# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2005



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Dr Timothy Norris'
_publ_contact_author_address     
;
Chemical Research & Development
Pfizer Global Research & Development
Eastern Point Road
Groton
CT
06340
;

_publ_contact_author_email       'TIMOTHY NORRIS@GROTON.PFIZER.COM'

_publ_section_title              
;
New hydroxy-pyrazoline intermediates, subtle
regio-selectivity and relative reaction rates variation observed
during acid catalyzed and neutral pyrazole cyclization
;
loop_
_publ_author_name
'Timothy Norris'
'Roberto Colon-Cruz'
'David H.B. Ripin'

data_f783
_database_code_depnum_ccdc_archive 'CCDC 263085'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 F2 N3 O3 S'
_chemical_formula_weight         367.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5772(4)
_cell_length_b                   17.2951(7)
_cell_length_c                   9.3940(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.7810(10)
_cell_angle_gamma                90.00
_cell_volume                     1617.08(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       PRISM
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    2.188
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3360
_diffrn_reflns_av_R_equivalents  0.1021
_diffrn_reflns_av_sigmaI/netI    0.0686
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.44
_diffrn_reflns_theta_max         44.94
_reflns_number_total             1285
_reflns_number_gt                1150
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR
and
goodness of fit S are based on F^2^, conventional R-factors R are
based
on F, with F set to zero for negative F^2^. The threshold expression
of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc.
and is
not relevant to the choice of reflections for refinement. R-factors
based
on F^2^ are statistically about twice as large as those based on F,
and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w=1/[\s^2^(Fo^2^)+(0.0926P)^2^+0.1467P] where
P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0236(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1285
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1276
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.1411(3) -0.05586(18) -0.3895(4) 0.0423(10) Uani 1 1 d . . .
C2 C -0.2015(4) -0.1093(2) -0.4798(4) 0.0420(11) Uani 1 1 d . . .
C3 C -0.1336(4) -0.1866(2) -0.4510(4) 0.0506(12) Uani 1 1 d . . .
H3A H -0.1163 -0.2052 -0.5389 0.080 Uiso 1 1 calc R . .
H3B H -0.1864 -0.2240 -0.4205 0.080 Uiso 1 1 calc R . .
C4 C -0.0021(4) -0.1682(2) -0.3216(4) 0.0409(11) Uani 1 1 d . . .
N5 N -0.0229(3) -0.08566(17) -0.2914(4) 0.0410(10) Uani 1 1 d . . .
C6 C 0.0591(4) -0.0406(2) -0.1783(4) 0.0369(11) Uani 1 1 d . . .
C7 C 0.0339(4) 0.0380(2) -0.1661(4) 0.0414(11) Uani 1 1 d . . .
H7 H -0.0453 0.0620 -0.2344 0.080 Uiso 1 1 calc R . .
C8 C 0.1251(4) 0.0798(2) -0.0540(5) 0.0445(12) Uani 1 1 d . . .
H8 H 0.1109 0.1339 -0.0429 0.080 Uiso 1 1 calc R . .
C9 C 0.2385(4) 0.0432(2) 0.0438(4) 0.0392(11) Uani 1 1 d . . .
C10 C 0.2515(4) -0.0351(3) 0.0266(4) 0.0441(11) Uani 1 1 d . . .
H10 H 0.3275 -0.0608 0.0972 0.080 Uiso 1 1 calc R . .
N11 N 0.1655(3) -0.07783(17) -0.0816(4) 0.0445(10) Uani 1 1 d . . .
C12 C 0.1221(4) -0.1777(2) -0.3666(4) 0.0379(11) Uani 1 1 d . . .
C13 C 0.1602(4) -0.1201(2) -0.4459(4) 0.0455(12) Uani 1 1 d . . .
H13 H 0.1096 -0.0729 -0.4692 0.080 Uiso 1 1 calc R . .
C14 C 0.2699(5) -0.1296(3) -0.4920(4) 0.0533(12) Uani 1 1 d . . .
H14 H 0.2948 -0.0891 -0.5472 0.080 Uiso 1 1 calc R . .
C15 C 0.3437(4) -0.1967(3) -0.4596(5) 0.0606(13) Uani 1 1 d . . .
H15 H 0.4204 -0.2030 -0.4913 0.080 Uiso 1 1 calc R . .
C16 C 0.3072(5) -0.2546(3) -0.3813(5) 0.0561(13) Uani 1 1 d . . .
H16 H 0.3592 -0.3014 -0.3577 0.080 Uiso 1 1 calc R . .
C17 C 0.1954(4) -0.2462(2) -0.3360(4) 0.0469(12) Uani 1 1 d . . .
H17 H 0.1691 -0.2876 -0.2838 0.080 Uiso 1 1 calc R . .
O18 O 0.0065(3) -0.21515(16) -0.1960(3) 0.0550(9) Uani 1 1 d D . .
H18 H -0.054(3) -0.204(3) -0.164(5) 0.080 Uiso 1 1 d D . .
C19 C -0.3326(4) -0.0908(3) -0.5983(5) 0.0555(13) Uani 1 1 d . . .
H19 H -0.3718 -0.0457 -0.5704 0.080 Uiso 1 1 calc R . .
F20 F -0.3153(3) -0.07983(19) -0.7320(3) 0.1081(12) Uani 1 1 d . . .
F21 F -0.4167(2) -0.15109(16) -0.6199(3) 0.0915(10) Uani 1 1 d . . .
S22 S 0.36482(10) 0.09377(6) 0.18241(11) 0.0494(6) Uani 1 1 d . . .
O23 O 0.3090(3) 0.16326(14) 0.2169(3) 0.0624(10) Uani 1 1 d . . .
O24 O 0.4303(3) 0.04123(16) 0.3030(3) 0.0675(10) Uani 1 1 d . . .
C25 C 0.4784(5) 0.1188(3) 0.0928(5) 0.0834(16) Uani 1 1 d . . .
H25A H 0.4341 0.1503 0.0061 0.080 Uiso 1 1 calc R . .
H25B H 0.5122 0.0728 0.0612 0.080 Uiso 1 1 calc R . .
H25C H 0.5517 0.1472 0.1617 0.080 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.037(2) 0.043(2) 0.042(2) 0.000(2) 0.0078(18) -0.003(2)
C2 0.033(3) 0.048(3) 0.042(3) -0.005(3) 0.009(2) -0.007(3)
C3 0.042(3) 0.043(3) 0.059(3) -0.006(2) 0.007(2) -0.001(2)
C4 0.044(3) 0.031(3) 0.041(3) 0.001(2) 0.005(2) 0.000(2)
N5 0.031(2) 0.037(2) 0.042(2) -0.0034(19) -0.003(2) 0.0047(18)
C6 0.030(3) 0.042(3) 0.035(3) -0.004(2) 0.006(2) -0.008(3)
C7 0.039(3) 0.035(3) 0.046(3) -0.001(2) 0.007(2) 0.003(2)
C8 0.044(3) 0.036(2) 0.050(3) -0.006(2) 0.012(2) -0.003(2)
C9 0.031(3) 0.042(3) 0.039(2) -0.006(2) 0.006(2) -0.002(2)
C10 0.033(3) 0.050(3) 0.041(3) -0.004(2) 0.001(2) 0.001(2)
N11 0.039(2) 0.042(2) 0.043(2) -0.0013(19) 0.001(2) 0.005(2)
C12 0.036(3) 0.037(3) 0.036(2) 0.001(2) 0.005(2) -0.003(2)
C13 0.041(3) 0.047(3) 0.046(3) 0.000(2) 0.011(2) 0.002(2)
C14 0.056(3) 0.052(3) 0.049(3) -0.006(2) 0.014(2) -0.009(3)
C15 0.046(3) 0.071(3) 0.059(3) -0.019(3) 0.010(3) -0.009(3)
C16 0.041(3) 0.049(3) 0.066(3) -0.013(3) 0.002(3) 0.011(2)
C17 0.045(3) 0.036(3) 0.048(3) -0.0020(19) 0.001(2) 0.003(2)
O18 0.056(2) 0.0529(18) 0.063(2) 0.0090(16) 0.0297(16) 0.0014(16)
C19 0.044(3) 0.066(3) 0.047(3) -0.008(2) 0.003(3) -0.008(3)
F20 0.075(2) 0.191(3) 0.0469(18) 0.0201(18) 0.0060(16) 0.0031(19)
F21 0.0492(17) 0.098(2) 0.101(2) -0.0064(16) -0.0080(15) -0.0241(17)
S22 0.0396(9) 0.0576(9) 0.0475(9) -0.0126(6) 0.0100(7) -0.0066(6)
O23 0.060(2) 0.0548(18) 0.0667(19) -0.0232(15) 0.0141(16) -0.0022(16)
O24 0.0548(19) 0.074(2) 0.0555(18) 0.0008(17) -0.0053(15) 0.0034(16)
C25 0.065(3) 0.118(4) 0.072(3) -0.038(3) 0.029(3) -0.039(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s.
planes)
are estimated using the full covariance matrix. The cell esds are
taken
into account individually in the estimation of esds in distances,
angles
and torsion angles; correlations between esds in cell parameters are
only
used when they are defined by crystal symmetry. An approximate
(isotropic)
treatment of cell esds is used for estimating esds involving l.s.
planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.271(4) . ?
N1 N5 1.378(4) . ?
C2 C19 1.490(5) . ?
C2 C3 1.497(5) . ?
C3 C4 1.539(5) . ?
C4 O18 1.409(4) . ?
C4 N5 1.486(5) . ?
C4 C12 1.519(6) . ?
N5 C6 1.366(4) . ?
C6 N11 1.347(4) . ?
C6 C7 1.397(5) . ?
C7 C8 1.369(5) . ?
C8 C9 1.392(5) . ?
C9 C10 1.376(5) . ?
C9 S22 1.752(4) . ?
C10 N11 1.335(4) . ?
C12 C13 1.383(5) . ?
C12 C17 1.392(5) . ?
C13 C14 1.379(5) . ?
C14 C15 1.373(6) . ?
C15 C16 1.374(6) . ?
C16 C17 1.393(6) . ?
C19 F21 1.340(5) . ?
C19 F20 1.343(5) . ?
S22 O23 1.424(3) . ?
S22 O24 1.434(3) . ?
S22 C25 1.739(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 N5 108.1(3) . . ?
N1 C2 C19 118.2(4) . . ?
N1 C2 C3 115.3(3) . . ?
C19 C2 C3 126.5(4) . . ?
C2 C3 C4 102.0(3) . . ?
O18 C4 N5 111.4(3) . . ?
O18 C4 C12 110.7(3) . . ?
N5 C4 C12 110.8(3) . . ?
O18 C4 C3 109.1(3) . . ?
N5 C4 C3 101.3(3) . . ?
C12 C4 C3 113.2(3) . . ?
C6 N5 N1 120.0(3) . . ?
C6 N5 C4 126.9(3) . . ?
N1 N5 C4 113.0(3) . . ?
N11 C6 N5 114.6(3) . . ?
N11 C6 C7 123.3(3) . . ?
N5 C6 C7 122.1(4) . . ?
C8 C7 C6 118.2(3) . . ?
C7 C8 C9 119.6(3) . . ?
C10 C9 C8 117.9(3) . . ?
C10 C9 S22 119.8(3) . . ?
C8 C9 S22 122.2(3) . . ?
N11 C10 C9 124.4(3) . . ?
C10 N11 C6 116.6(3) . . ?
C13 C12 C17 118.7(4) . . ?
C13 C12 C4 120.6(3) . . ?
C17 C12 C4 120.6(4) . . ?
C14 C13 C12 120.8(4) . . ?
C15 C14 C13 120.5(4) . . ?
C16 C15 C14 119.6(4) . . ?
C15 C16 C17 120.6(4) . . ?
C12 C17 C16 119.8(4) . . ?
F21 C19 F20 105.1(3) . . ?
F21 C19 C2 110.4(3) . . ?
F20 C19 C2 110.0(3) . . ?
O23 S22 O24 118.82(17) . . ?
O23 S22 C25 107.9(2) . . ?
O24 S22 C25 108.2(2) . . ?
O23 S22 C9 108.67(18) . . ?
O24 S22 C9 108.25(18) . . ?
C25 S22 C9 104.07(19) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        44.94
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.116

data_f596
_database_code_depnum_ccdc_archive 'CCDC 263086'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 F3 N3 O2 S'
_chemical_formula_weight         367.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.208(4)
_cell_length_b                   5.0510(10)
_cell_length_c                   21.756(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.080(10)
_cell_angle_gamma                90.00
_cell_volume                     3221.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    42
_cell_measurement_theta_min      5.998
_cell_measurement_theta_max      54.666

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    2.245
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'theta and 2theta scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1679
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         49.99
_reflns_number_total             1639
_reflns_number_gt                1245
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR
and
goodness of fit S are based on F^2^, conventional R-factors R are
based
on F, with F set to zero for negative F^2^. The threshold expression
of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc.
and is
not relevant to the choice of reflections for refinement. R-factors
based
on F^2^ are statistically about twice as large as those based on F,
and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+4.2154P] where
P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00052(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1639
_refine_ls_number_parameters     285
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.004

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.12380(12) 0.4532(8) 0.49292(17) 0.0417(10) Uani 1 1 d . . .
N2 N 0.12326(13) 0.3935(8) 0.43149(17) 0.0480(11) Uani 1 1 d . . .
C3 C 0.09029(16) 0.2176(10) 0.40923(18) 0.0520(14) Uani 1 1 d D . .
C4 C 0.06977(16) 0.1609(12) 0.4555(2) 0.0598(15) Uani 1 1 d . . .
H4A H 0.0461 0.0419 0.4509 0.080 Uiso 1 1 calc R . .
C5 C 0.09106(15) 0.3136(10) 0.5087(2) 0.0436(13) Uani 1 1 d . . .
C6 C 0.15726(14) 0.6401(9) 0.5292(2) 0.0378(12) Uani 1 1 d . . .
N7 N 0.16382(14) 0.6567(9) 0.59159(19) 0.0596(13) Uani 1 1 d . . .
C8 C 0.19543(17) 0.8278(12) 0.6266(2) 0.0584(15) Uani 1 1 d . . .
H8A H 0.2002 0.8436 0.6710 0.080 Uiso 1 1 calc R . .
C9 C 0.22111(14) 0.9810(9) 0.6007(2) 0.0365(12) Uani 1 1 d . . .
C10 C 0.21305(18) 0.9604(10) 0.5349(2) 0.0566(14) Uani 1 1 d . . .
H10A H 0.2295 1.0636 0.5154 0.080 Uiso 1 1 calc R . .
C11 C 0.18051(18) 0.7862(11) 0.4979(2) 0.0597(16) Uani 1 1 d . . .
H11D H 0.1745 0.7682 0.4531 0.080 Uiso 1 1 calc R . .
S12 S 0.26348(4) 1.1937(2) 0.65098(6) 0.0456(5) Uani 1 1 d . . .
O13 O 0.27701(12) 1.3662(7) 0.60864(15) 0.0661(11) Uani 1 1 d . . .
O14 O 0.24764(11) 1.3075(7) 0.69937(15) 0.0608(10) Uani 1 1 d . . .
C15 C 0.30840(16) 0.9798(11) 0.6914(2) 0.0642(16) Uani 1 1 d . . .
H15A H 0.3200 0.9005 0.6601 0.080 Uiso 1 1 calc R . .
H15B H 0.2976 0.8438 0.7132 0.080 Uiso 1 1 calc R . .
H15C H 0.3323 1.0777 0.7230 0.080 Uiso 1 1 calc R . .
C16 C 0.07898(17) 0.1065(12) 0.3423(2) 0.0670(17) Uani 1 1 d D . .
F17 F 0.0559(8) 0.269(2) 0.2977(3) 0.107(4) Uani 0.50 1 d PD . .
F18 F 0.0538(5) -0.112(2) 0.3357(5) 0.076(3) Uani 0.50 1 d PD . .
F19 F 0.1153(2) 0.024(4) 0.3303(6) 0.087(4) Uani 0.50 1 d PD . .
F17A F 0.0960(8) 0.258(4) 0.3056(5) 0.109(4) Uani 0.50 1 d PD . .
F18A F 0.0942(11) -0.130(3) 0.3417(5) 0.210(10) Uani 0.50 1 d PD . .
F19A F 0.0349(2) 0.113(6) 0.3103(6) 0.142(7) Uani 0.50 1 d PD . .
C20 C 0.0786(3) 0.3457(17) 0.5681(3) 0.046(13) Uani 0.50 1 d PG . .
C21 C 0.10909(18) 0.2760(15) 0.6293(4) 0.045(3) Uani 0.50 1 d PG . .
C22 C 0.0944(3) 0.2627(16) 0.6827(3) 0.059(3) Uani 0.50 1 d PG . .
C23 C 0.0492(3) 0.3193(18) 0.6749(3) 0.079(13) Uani 0.50 1 d PG . .
C24 C 0.0188(2) 0.3890(16) 0.6137(4) 0.057(3) Uani 0.50 1 d PG . .
C25 C 0.0335(2) 0.4023(16) 0.5603(3) 0.052(3) Uani 0.50 1 d PG . .
H21A H 0.1401 0.2374 0.6350 0.080 Uiso 0.50 1 d P . .
H22A H 0.1151 0.2114 0.7254 0.080 Uiso 0.50 1 d P . .
H23A H 0.0386 0.3073 0.7123 0.080 Uiso 0.50 1 d P . .
H24A H -0.0129 0.4290 0.6089 0.080 Uiso 0.50 1 d P . .
H25A H 0.0121 0.4549 0.5184 0.080 Uiso 0.50 1 d P . .
C20X C 0.0795(2) 0.3224(19) 0.5697(3) 0.037(12) Uani 0.50 1 d PG . .
C21X C 0.0734(3) 0.0918(14) 0.6007(4) 0.058(3) Uani 0.50 1 d PG . .
C22X C 0.0580(3) 0.1060(16) 0.6534(4) 0.074(4) Uani 0.50 1 d PG . .
C23X C 0.0486(2) 0.351(2) 0.6751(3) 0.054(10) Uani 0.50 1 d PG . .
C24X C 0.0547(3) 0.5811(15) 0.6442(4) 0.061(3) Uani 0.50 1 d PG . .
C25X C 0.0702(3) 0.5670(15) 0.5915(4) 0.049(3) Uani 0.50 1 d PG . .
H21X H 0.0802 -0.0785 0.5865 0.080 Uiso 0.50 1 d P . .
H22X H 0.0540 -0.0533 0.6757 0.080 Uiso 0.50 1 d P . .
H23X H 0.0376 0.3616 0.7119 0.080 Uiso 0.50 1 d P . .
H24X H 0.0475 0.7513 0.6588 0.080 Uiso 0.50 1 d P . .
H25X H 0.0738 0.7260 0.5696 0.080 Uiso 0.50 1 d P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.042(2) 0.047(3) 0.033(2) -0.002(2) 0.0094(19) -0.002(2)
N2 0.049(3) 0.060(3) 0.033(2) -0.003(2) 0.011(2) -0.001(2)
C3 0.042(3) 0.070(4) 0.040(3) -0.007(3) 0.009(3) -0.006(3)
C4 0.048(3) 0.080(4) 0.049(3) -0.013(3) 0.013(3) -0.017(3)
C5 0.035(3) 0.054(3) 0.041(3) 0.001(3) 0.011(2) 0.000(3)
C6 0.038(3) 0.036(3) 0.038(3) 0.001(2) 0.011(2) 0.004(2)
N7 0.054(3) 0.088(4) 0.038(3) -0.009(2) 0.018(2) -0.032(3)
C8 0.055(3) 0.087(4) 0.035(3) -0.005(3) 0.017(3) -0.018(3)
C9 0.040(3) 0.036(3) 0.035(3) 0.000(2) 0.014(2) 0.000(2)
C10 0.076(4) 0.056(4) 0.045(3) -0.002(3) 0.029(3) -0.021(3)
C11 0.086(4) 0.062(4) 0.034(3) -0.009(3) 0.023(3) -0.021(3)
S12 0.0512(8) 0.0410(8) 0.0441(8) -0.0025(6) 0.0157(6) -0.0048(7)
O13 0.081(3) 0.063(3) 0.056(2) 0.0051(19) 0.0261(19) -0.027(2)
O14 0.080(3) 0.053(2) 0.055(2) -0.0140(19) 0.0298(19) 0.002(2)
C15 0.048(3) 0.063(4) 0.071(4) -0.004(3) 0.007(3) -0.002(3)
C16 0.051(4) 0.097(6) 0.052(4) -0.012(4) 0.016(3) -0.022(4)
F17 0.151(12) 0.093(8) 0.033(4) 0.004(4) -0.026(7) 0.012(8)
F18 0.086(6) 0.075(7) 0.071(6) -0.032(5) 0.033(6) -0.025(6)
F19 0.061(5) 0.141(13) 0.064(7) -0.040(9) 0.028(4) -0.009(7)
F17A 0.129(9) 0.144(12) 0.053(6) -0.023(6) 0.031(7) -0.061(10)
F18A 0.42(3) 0.102(14) 0.073(7) -0.015(8) 0.032(18) 0.114(18)
F19A 0.064(6) 0.27(2) 0.084(8) -0.079(11) 0.014(6) -0.050(12)
C20 0.03(2) 0.05(2) 0.05(2) 0.027(13) -0.003(18) -0.009(13)
C21 0.045(6) 0.044(7) 0.049(7) 0.010(5) 0.018(6) -0.002(6)
C22 0.065(8) 0.064(8) 0.041(6) 0.004(6) 0.010(6) -0.019(7)
C23 0.15(3) 0.057(19) 0.05(2) -0.004(13) 0.05(2) -0.038(17)
C24 0.059(7) 0.052(8) 0.073(8) 0.002(6) 0.039(7) 0.001(6)
C25 0.037(6) 0.057(7) 0.057(7) 0.005(6) 0.009(5) 0.000(6)
C20X 0.04(2) 0.035(19) 0.04(2) -0.024(11) 0.020(19) 0.003(13)
C21X 0.072(8) 0.030(7) 0.077(8) 0.002(6) 0.034(7) -0.001(6)
C22X 0.106(10) 0.074(10) 0.059(8) 0.003(7) 0.051(7) -0.028(8)
C23X 0.036(13) 0.073(19) 0.06(2) -0.023(13) 0.033(14) -0.009(12)
C24X 0.060(7) 0.055(9) 0.075(8) -0.016(7) 0.036(6) -0.015(6)
C25X 0.048(7) 0.045(8) 0.053(7) -0.001(6) 0.017(6) -0.006(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s.
planes)
are estimated using the full covariance matrix. The cell esds are
taken
into account individually in the estimation of esds in distances,
angles
and torsion angles; correlations between esds in cell parameters are
only
used when they are defined by crystal symmetry. An approximate
(isotropic)
treatment of cell esds is used for estimating esds involving l.s.
planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.365(5) . ?
N1 C5 1.379(6) . ?
N1 C6 1.428(6) . ?
N2 C3 1.319(6) . ?
C3 C4 1.396(6) . ?
C3 C16 1.486(5) . ?
C4 C5 1.360(6) . ?
C5 C20 1.479(7) . ?
C5 C20X 1.490(7) . ?
C6 N7 1.303(5) . ?
C6 C11 1.370(6) . ?
N7 C8 1.336(6) . ?
C8 C9 1.367(6) . ?
C9 C10 1.368(6) . ?
C9 S12 1.763(4) . ?
C10 C11 1.376(7) . ?
S12 O14 1.428(3) . ?
S12 O13 1.433(3) . ?
S12 C15 1.749(5) . ?
C16 F17 1.286(7) . ?
C16 F18A 1.288(8) . ?
C16 F19A 1.311(8) . ?
C16 F19 1.314(7) . ?
C16 F18 1.334(7) . ?
C16 F17A 1.339(7) . ?
F17 F19A 1.119(12) . ?
F17 F17A 1.203(11) . ?
F18 F18A 1.22(2) . ?
F18 F19A 1.311(18) . ?
F19 F18A 1.10(2) . ?
F19 F17A 1.350(13) . ?
C20 C25X 1.293(11) . ?
C20 C21 1.3900 . ?
C20 C25 1.3900 . ?
C20 C21X 1.501(11) . ?
C21 C20X 1.328(11) . ?
C21 C22 1.3900 . ?
C21 C21X 1.419(11) . ?
C21 C25X 1.904(10) . ?
C21 C22X 2.032(10) . ?
C22 C22X 1.352(11) . ?
C22 C23 1.3900 . ?
C22 C23X 1.450(12) . ?
C22 C21X 1.886(10) . ?
C22 C24X 2.027(10) . ?
C23 C22X 1.242(12) . ?
C23 C24 1.3900 . ?
C23 C24X 1.518(12) . ?
C24 C23X 1.355(11) . ?
C24 C25 1.3900 . ?
C24 C24X 1.459(11) . ?
C24 C22X 1.887(11) . ?
C24 C25X 2.036(10) . ?
C25 C25X 1.389(10) . ?
C25 C20X 1.438(11) . ?
C25 C24X 1.939(10) . ?
C25 C21X 2.008(10) . ?
C20X C21X 1.3900 . ?
C20X C25X 1.3900 . ?
C21X C22X 1.3900 . ?
C22X C23X 1.3900 . ?
C23X C24X 1.3900 . ?
C24X C25X 1.3900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C5 111.7(4) . . ?
N2 N1 C6 116.7(4) . . ?
C5 N1 C6 131.6(4) . . ?
C3 N2 N1 104.7(3) . . ?
N2 C3 C4 111.5(4) . . ?
N2 C3 C16 120.5(4) . . ?
C4 C3 C16 128.1(5) . . ?
C5 C4 C3 106.7(4) . . ?
C4 C5 N1 105.4(4) . . ?
C4 C5 C20 127.4(5) . . ?
N1 C5 C20 126.9(5) . . ?
C4 C5 C20X 125.3(5) . . ?
N1 C5 C20X 129.3(5) . . ?
C20 C5 C20X 4.8(5) . . ?
N7 C6 C11 124.3(4) . . ?
N7 C6 N1 116.3(4) . . ?
C11 C6 N1 119.5(4) . . ?
C6 N7 C8 117.1(4) . . ?
N7 C8 C9 123.7(4) . . ?
C10 C9 C8 117.7(4) . . ?
C10 C9 S12 121.7(4) . . ?
C8 C9 S12 120.7(4) . . ?
C9 C10 C11 119.7(4) . . ?
C6 C11 C10 117.6(4) . . ?
O14 S12 O13 118.8(2) . . ?
O14 S12 C15 107.4(2) . . ?
O13 S12 C15 109.7(2) . . ?
O14 S12 C9 109.1(2) . . ?
O13 S12 C9 107.2(2) . . ?
C15 S12 C9 103.7(2) . . ?
F17 C16 F18A 134.3(7) . . ?
F17 C16 F19A 51.0(6) . . ?
F18A C16 F19A 109.9(8) . . ?
F17 C16 F19 110.5(7) . . ?
F18A C16 F19 50.2(10) . . ?
F19A C16 F19 136.1(7) . . ?
F17 C16 F18 107.0(6) . . ?
F18A C16 F18 55.6(11) . . ?
F19A C16 F18 59.4(8) . . ?
F19 C16 F18 103.5(6) . . ?
F17 C16 F17A 54.5(6) . . ?
F18A C16 F17A 107.6(8) . . ?
F19A C16 F17A 103.2(7) . . ?
F19 C16 F17A 61.1(6) . . ?
F18 C16 F17A 138.4(6) . . ?
F17 C16 C3 112.4(5) . . ?
F18A C16 C3 113.3(6) . . ?
F19A C16 C3 111.4(6) . . ?
F19 C16 C3 112.5(5) . . ?
F18 C16 C3 110.5(5) . . ?
F17A C16 C3 111.0(5) . . ?
F19A F17 F17A 126.8(10) . . ?
F19A F17 C16 65.6(6) . . ?
F17A F17 C16 65.0(5) . . ?
F18A F18 F19A 114.0(9) . . ?
F18A F18 C16 60.3(7) . . ?
F19A F18 C16 59.4(5) . . ?
F18A F19 C16 63.7(8) . . ?
F18A F19 F17A 119.3(10) . . ?
C16 F19 F17A 60.4(5) . . ?
F17 F17A C16 60.5(5) . . ?
F17 F17A F19 113.4(8) . . ?
C16 F17A F19 58.5(5) . . ?
F19 F18A F18 126.5(10) . . ?
F19 F18A C16 66.1(6) . . ?
F18 F18A C16 64.1(7) . . ?
F17 F19A C16 63.3(5) . . ?
F17 F19A F18 119.9(11) . . ?
C16 F19A F18 61.2(7) . . ?
C25X C20 C21 90.4(5) . . ?
C25X C20 C25 62.3(5) . . ?
C21 C20 C25 120.0 . . ?
C25X C20 C5 126.1(7) . . ?
C21 C20 C5 120.7(6) . . ?
C25 C20 C5 118.4(6) . . ?
C25X C20 C21X 118.8(6) . . ?
C21 C20 C21X 58.7(4) . . ?
C25 C20 C21X 87.9(4) . . ?
C5 C20 C21X 115.0(7) . . ?
C20X C21 C22 120.4(4) . . ?
C20X C21 C20 4.5(5) . . ?
C22 C21 C20 120.0 . . ?
C20X C21 C21X 60.7(4) . . ?
C22 C21 C21X 84.3(5) . . ?
C20 C21 C21X 64.6(5) . . ?
C20X C21 C25X 46.9(3) . . ?
C22 C21 C25X 93.0(3) . . ?
C20 C21 C25X 42.8(4) . . ?
C21X C21 C25X 91.6(4) . . ?
C20X C21 C22X 89.0(4) . . ?
C22 C21 C22X 41.5(4) . . ?
C20 C21 C22X 90.9(3) . . ?
C21X C21 C22X 43.1(3) . . ?
C25X C21 C22X 89.8(3) . . ?
C22X C22 C21 95.6(5) . . ?
C22X C22 C23 53.9(5) . . ?
C21 C22 C23 120.0 . . ?
C22X C22 C23X 59.3(4) . . ?
C21 C22 C23X 119.0(4) . . ?
C23 C22 C23X 6.0(5) . . ?
C22X C22 C21X 47.4(3) . . ?
C21 C22 C21X 48.5(4) . . ?
C23 C22 C21X 88.3(3) . . ?
C23X C22 C21X 91.4(4) . . ?
C22X C22 C24X 88.5(5) . . ?
C21 C22 C24X 86.9(3) . . ?
C23 C22 C24X 48.4(3) . . ?
C23X C22 C24X 43.3(3) . . ?
C21X C22 C24X 90.5(3) . . ?
C22X C23 C24 91.4(5) . . ?
C22X C23 C22 61.5(5) . . ?
C24 C23 C22 120.0 . . ?
C22X C23 C24X 121.1(6) . . ?
C24 C23 C24X 60.0(4) . . ?
C22 C23 C24X 88.3(4) . . ?
C23X C24 C25 121.3(4) . . ?
C23X C24 C23 6.5(5) . . ?
C25 C24 C23 120.0 . . ?
C23X C24 C24X 59.1(4) . . ?
C25 C24 C24X 85.7(5) . . ?
C23 C24 C24X 64.3(5) . . ?
C23X C24 C22X 47.4(3) . . ?
C25 C24 C22X 94.0(4) . . ?
C23 C24 C22X 41.2(4) . . ?
C24X C24 C22X 91.1(4) . . ?
C23X C24 C25X 88.1(4) . . ?
C25 C24 C25X 42.9(3) . . ?
C23 C24 C25X 90.2(3) . . ?
C24X C24 C25X 43.1(3) . . ?
C22X C24 C25X 90.2(3) . . ?
C25X C25 C24 94.2(5) . . ?
C25X C25 C20 55.5(5) . . ?
C24 C25 C20 120.0 . . ?
C25X C25 C20X 58.9(4) . . ?
C24 C25 C20X 117.9(4) . . ?
C20 C25 C20X 4.6(5) . . ?
C25X C25 C24X 45.8(3) . . ?
C24 C25 C24X 48.6(4) . . ?
C20 C25 C24X 88.7(3) . . ?
C20X C25 C24X 89.7(4) . . ?
C25X C25 C21X 88.3(4) . . ?
C24 C25 C21X 86.0(3) . . ?
C20 C25 C21X 48.3(3) . . ?
C20X C25 C21X 43.8(3) . . ?
C24X C25 C21X 89.5(3) . . ?
C21 C20X C21X 62.9(5) . . ?
C21 C20X C25X 88.9(5) . . ?
C21X C20X C25X 120.0 . . ?
C21 C20X C25 121.0(6) . . ?
C21X C20X C25 90.5(4) . . ?
C25X C20X C25 58.8(4) . . ?
C21 C20X C5 124.4(6) . . ?
C21X C20X C5 121.4(7) . . ?
C25X C20X C5 118.2(7) . . ?
C25 C20X C5 114.6(5) . . ?
C20X C21X C22X 120.0 . . ?
C20X C21X C21 56.4(5) . . ?
C22X C21X C21 92.7(5) . . ?
C20X C21X C20 2.2(4) . . ?
C22X C21X C20 118.0(4) . . ?
C21 C21X C20 56.8(4) . . ?
C20X C21X C22 90.8(3) . . ?
C22X C21X C22 45.7(4) . . ?
C21 C21X C22 47.2(3) . . ?
C20 C21X C22 89.9(4) . . ?
C20X C21X C25 45.7(3) . . ?
C22X C21X C25 88.9(3) . . ?
C21 C21X C25 87.5(4) . . ?
C20 C21X C25 43.8(3) . . ?
C22 C21X C25 91.0(3) . . ?
C23 C22X C22 64.6(5) . . ?
C23 C22X C23X 2.7(4) . . ?
C22 C22X C23X 63.9(5) . . ?
C23 C22X C21X 122.6(4) . . ?
C22 C22X C21X 86.9(5) . . ?
C23X C22X C21X 120.0 . . ?
C23 C22X C24 47.4(4) . . ?
C22 C22X C24 94.6(5) . . ?
C23X C22X C24 45.8(4) . . ?
C21X C22X C24 90.9(3) . . ?
C23 C22X C21 91.4(5) . . ?
C22 C22X C21 42.9(3) . . ?
C23X C22X C21 89.3(3) . . ?
C21X C22X C21 44.2(3) . . ?
C24 C22X C21 90.3(3) . . ?
C24 C23X C22X 86.8(5) . . ?
C24 C23X C24X 64.2(5) . . ?
C22X C23X C24X 120.0 . . ?
C24 C23X C22 118.2(6) . . ?
C22X C23X C22 56.8(5) . . ?
C24X C23X C22 91.1(4) . . ?
C23X C24X C25X 120.0 . . ?
C23X C24X C24 56.7(5) . . ?
C25X C24X C24 91.2(4) . . ?
C23X C24X C23 3.8(4) . . ?
C25X C24X C23 116.2(4) . . ?
C24 C24X C23 55.6(4) . . ?
C23X C24X C25 90.4(3) . . ?
C25X C24X C25 45.8(4) . . ?
C24 C24X C25 45.6(3) . . ?
C23 C24X C25 87.4(4) . . ?
C23X C24X C22 45.7(3) . . ?
C25X C24X C22 87.9(3) . . ?
C24 C24X C22 85.7(4) . . ?
C23 C24X C22 43.3(3) . . ?
C25 C24X C22 89.0(3) . . ?
C20 C25X C25 62.3(5) . . ?
C20 C25X C24X 123.1(4) . . ?
C25 C25X C24X 88.5(5) . . ?
C20 C25X C20X 3.3(4) . . ?
C25 C25X C20X 62.3(5) . . ?
C24X C25X C20X 120.0 . . ?
C20 C25X C21 46.9(3) . . ?
C25 C25X C21 92.6(5) . . ?
C24X C25X C21 92.0(4) . . ?
C20X C25X C21 44.2(4) . . ?
C20 C25X C24 89.8(4) . . ?
C25 C25X C24 42.9(3) . . ?
C24X C25X C24 45.8(3) . . ?
C20X C25X C24 87.9(3) . . ?
C21 C25X C24 89.7(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        49.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.044

data_f579
_database_code_depnum_ccdc_archive 'CCDC 263087'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 F2 N3 O2 S'
_chemical_formula_weight         349.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.614(2)
_cell_length_b                   7.4840(10)
_cell_length_c                   20.523(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.250(10)
_cell_angle_gamma                90.00
_cell_volume                     1620.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       PRISM
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    2.108
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1790
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.19
_diffrn_reflns_theta_max         49.98
_reflns_number_total             1674
_reflns_number_gt                1271
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR
and
goodness of fit S are based on F^2^, conventional R-factors R are
based
on F, with F set to zero for negative F^2^. The threshold expression
of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc.
and is
not relevant to the choice of reflections for refinement. R-factors
based
on F^2^ are statistically about twice as large as those based on F,
and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+0.4721P] where
P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1674
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1X S 0.53678(10) 0.07320(14) 0.13470(5) 0.0474(4) Uani 1 1 d . . .
C1 C 0.6923(4) -0.4103(5) 0.17403(18) 0.0395(10) Uani 1 1 d . . .
H1B H 0.6923 -0.5017 0.2047 0.080 Uiso 1 1 calc R . .
C2 C 0.6245(4) -0.2552(5) 0.18015(19) 0.0425(11) Uani 1 1 d . . .
H2B H 0.5787 -0.2379 0.2158 0.080 Uiso 1 1 calc R . .
C3 C 0.6259(3) -0.1257(5) 0.13194(18) 0.0341(10) Uani 1 1 d . . .
C4 C 0.6990(4) -0.1522(5) 0.08154(18) 0.0421(11) Uani 1 1 d . . .
H4B H 0.7006 -0.0631 0.0500 0.080 Uiso 1 1 calc R . .
N5 N 0.7679(3) -0.2999(4) 0.07550(15) 0.0409(9) Uani 1 1 d . . .
C6 C 0.7603(3) -0.4249(5) 0.12067(17) 0.0320(9) Uani 1 1 d . . .
N7 N 0.8295(3) -0.5840(4) 0.11201(14) 0.0356(8) Uani 1 1 d . . .
N8 N 0.8810(3) -0.6684(4) 0.16759(15) 0.0419(9) Uani 1 1 d . . .
C9 C 0.9420(4) -0.8066(5) 0.14508(19) 0.0418(10) Uani 1 1 d . . .
C10 C 0.9306(4) -0.8132(5) 0.07702(19) 0.0428(11) Uani 1 1 d . . .
H10B H 0.9655 -0.8980 0.0512 0.080 Uiso 1 1 calc R . .
C11 C 0.8573(3) -0.6688(5) 0.05564(18) 0.0349(10) Uani 1 1 d . . .
C12 C 0.8096(3) -0.6191(5) -0.01192(17) 0.0342(10) Uani 1 1 d . . .
C13 C 0.6855(4) -0.5654(5) -0.0298(2) 0.0461(11) Uani 1 1 d . . .
H13B H 0.6295 -0.5575 0.0019 0.080 Uiso 1 1 calc R . .
C14 C 0.6446(5) -0.5239(6) -0.0938(2) 0.0576(13) Uani 1 1 d . . .
H14B H 0.5614 -0.4876 -0.1052 0.080 Uiso 1 1 calc R . .
C15 C 0.7266(6) -0.5360(6) -0.1409(2) 0.0687(15) Uani 1 1 d . . .
H15B H 0.6991 -0.5063 -0.1841 0.080 Uiso 1 1 calc R . .
C16 C 0.8497(5) -0.5922(6) -0.1244(2) 0.0650(14) Uani 1 1 d . . .
H16B H 0.9044 -0.6036 -0.1566 0.080 Uiso 1 1 calc R . .
C17 C 0.8914(4) -0.6313(5) -0.0603(2) 0.0486(11) Uani 1 1 d . . .
H17B H 0.9750 -0.6663 -0.0491 0.080 Uiso 1 1 calc R . .
C18 C 1.0086(4) -0.9308(6) 0.1940(2) 0.0521(12) Uani 1 1 d . . .
H18B H 1.0149 -0.8788 0.2380 0.080 Uiso 1 1 calc R . .
F19 F 0.9482(3) -1.0893(4) 0.19267(17) 0.1126(13) Uani 1 1 d . . .
F20 F 1.1234(3) -0.9713(5) 0.17728(15) 0.1089(13) Uani 1 1 d . . .
O21 O 0.5449(4) 0.1342(5) 0.20054(16) 0.0854(11) Uani 1 1 d . . .
O22 O 0.5756(3) 0.1905(4) 0.08583(17) 0.0782(11) Uani 1 1 d . . .
C23 C 0.3814(4) 0.0083(7) 0.1108(3) 0.0802(17) Uani 1 1 d . . .
H23A H 0.3266 0.1102 0.1112 0.080 Uiso 1 1 calc R . .
H23B H 0.3564 -0.0803 0.1407 0.080 Uiso 1 1 calc R . .
H23C H 0.3755 -0.0410 0.0674 0.080 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1X 0.0469(7) 0.0366(7) 0.0607(8) -0.0051(6) 0.0152(5) 0.0063(5)
C1 0.040(2) 0.042(3) 0.036(2) 0.000(2) 0.0043(19) 0.001(2)
C2 0.041(3) 0.049(3) 0.040(3) -0.003(2) 0.013(2) 0.002(2)
C3 0.035(2) 0.031(2) 0.038(2) -0.005(2) 0.0074(19) 0.0012(18)
C4 0.052(3) 0.035(3) 0.040(3) 0.000(2) 0.012(2) 0.002(2)
N5 0.046(2) 0.038(2) 0.040(2) -0.0021(18) 0.0120(16) 0.0025(18)
C6 0.030(2) 0.033(2) 0.033(2) -0.004(2) 0.0019(18) 0.002(2)
N7 0.0368(18) 0.037(2) 0.0321(19) -0.0001(17) 0.0018(15) 0.0073(17)
N8 0.043(2) 0.042(2) 0.040(2) 0.0038(18) -0.0012(16) 0.0088(19)
C9 0.040(2) 0.043(3) 0.041(3) -0.001(2) 0.002(2) 0.009(2)
C10 0.046(2) 0.039(3) 0.043(3) -0.003(2) 0.003(2) 0.010(2)
C11 0.034(2) 0.037(2) 0.034(2) -0.002(2) 0.0062(18) 0.003(2)
C12 0.035(2) 0.032(2) 0.035(2) -0.0047(19) 0.0011(19) -0.0006(19)
C13 0.047(3) 0.044(3) 0.044(3) -0.010(2) -0.006(2) 0.002(2)
C14 0.063(3) 0.045(3) 0.059(3) -0.011(2) -0.019(3) 0.008(2)
C15 0.107(5) 0.053(3) 0.042(3) 0.003(2) -0.012(3) -0.001(3)
C16 0.092(4) 0.062(3) 0.044(3) 0.001(3) 0.022(3) -0.001(3)
C17 0.051(3) 0.053(3) 0.043(3) -0.005(2) 0.010(2) -0.003(2)
C18 0.049(3) 0.045(3) 0.060(3) -0.001(2) -0.004(2) 0.008(3)
F19 0.122(3) 0.067(2) 0.133(3) 0.037(2) -0.060(2) -0.012(2)
F20 0.077(2) 0.154(3) 0.098(2) 0.042(2) 0.0150(17) 0.067(2)
O21 0.107(3) 0.082(3) 0.067(2) -0.033(2) 0.0107(19) 0.036(2)
O22 0.083(2) 0.0459(19) 0.114(3) 0.0266(19) 0.047(2) 0.0139(18)
C23 0.044(3) 0.055(3) 0.141(5) 0.002(3) 0.007(3) 0.012(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s.
planes)
are estimated using the full covariance matrix. The cell esds are
taken
into account individually in the estimation of esds in distances,
angles
and torsion angles; correlations between esds in cell parameters are
only
used when they are defined by crystal symmetry. An approximate
(isotropic)
treatment of cell esds is used for estimating esds involving l.s.
planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1X O21 1.420(3) . ?
S1X O22 1.427(3) . ?
S1X C23 1.737(5) . ?
S1X C3 1.768(4) . ?
C1 C2 1.379(5) . ?
C1 C6 1.380(5) . ?
C2 C3 1.386(5) . ?
C3 C4 1.373(5) . ?
C4 N5 1.339(5) . ?
N5 C6 1.326(5) . ?
C6 N7 1.420(5) . ?
N7 N8 1.365(4) . ?
N7 C11 1.379(4) . ?
N8 C9 1.329(5) . ?
C9 C10 1.390(5) . ?
C9 C18 1.489(6) . ?
C10 C11 1.375(5) . ?
C11 C12 1.471(5) . ?
C12 C13 1.387(5) . ?
C12 C17 1.391(5) . ?
C13 C14 1.374(6) . ?
C14 C15 1.372(6) . ?
C15 C16 1.379(7) . ?
C16 C17 1.372(6) . ?
C18 F20 1.337(5) . ?
C18 F19 1.347(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O21 S1X O22 118.6(2) . . ?
O21 S1X C23 108.4(3) . . ?
O22 S1X C23 108.2(2) . . ?
O21 S1X C3 108.90(19) . . ?
O22 S1X C3 107.39(18) . . ?
C23 S1X C3 104.5(2) . . ?
C2 C1 C6 117.5(4) . . ?
C1 C2 C3 118.5(3) . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 S1X 119.6(3) . . ?
C2 C3 S1X 121.2(3) . . ?
N5 C4 C3 123.2(4) . . ?
C6 N5 C4 116.2(3) . . ?
N5 C6 C1 125.2(4) . . ?
N5 C6 N7 115.6(3) . . ?
C1 C6 N7 119.2(3) . . ?
N8 N7 C11 112.7(3) . . ?
N8 N7 C6 116.7(3) . . ?
C11 N7 C6 130.6(3) . . ?
C9 N8 N7 103.6(3) . . ?
N8 C9 C10 112.6(3) . . ?
N8 C9 C18 117.7(4) . . ?
C10 C9 C18 129.7(4) . . ?
C11 C10 C9 106.1(3) . . ?
C10 C11 N7 105.0(3) . . ?
C10 C11 C12 128.6(3) . . ?
N7 C11 C12 126.2(3) . . ?
C13 C12 C17 118.6(4) . . ?
C13 C12 C11 122.8(3) . . ?
C17 C12 C11 118.6(3) . . ?
C14 C13 C12 120.7(4) . . ?
C15 C14 C13 120.0(4) . . ?
C14 C15 C16 120.2(4) . . ?
C17 C16 C15 119.9(4) . . ?
C16 C17 C12 120.6(4) . . ?
F20 C18 F19 103.9(4) . . ?
F20 C18 C9 110.4(4) . . ?
F19 C18 C9 110.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        49.98
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042


data_f874
_database_code_depnum_ccdc_archive 'CCDC 263088'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N3 O3 S'
_chemical_formula_weight         331.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.9809(10)
_cell_length_b                   9.4557(6)
_cell_length_c                   10.5313(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.4710(10)
_cell_angle_gamma                90.00
_cell_volume                     1591.34(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       PRISM
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8021
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         20.82
_reflns_number_total             1663
_reflns_number_gt                1342
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR
and
goodness of fit S are based on F^2^, conventional R-factors R are
based
on F, with F set to zero for negative F^2^. The threshold expression
of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc.
and is
not relevant to the choice of reflections for refinement. R-factors
based
on F^2^ are statistically about twice as large as those based on F,
and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w=1/[\s^2^(Fo^2^)+(0.0635P)^2^+0.0000P] where
P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0120(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1663
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.20483(13) 0.3613(2) 0.5908(2) 0.0472(6) Uani 1 1 d . . .
C2 C -0.12782(17) 0.3570(3) 0.6410(3) 0.0470(8) Uani 1 1 d . . .
H2 H -0.1105 0.4326 0.6962 0.080 Uiso 1 1 calc R . .
C3 C -0.07207(16) 0.2491(3) 0.6173(2) 0.0423(7) Uani 1 1 d . . .
C4 C -0.09800(18) 0.1390(3) 0.5396(3) 0.0506(8) Uani 1 1 d . . .
H4 H -0.0608 0.0617 0.5223 0.080 Uiso 1 1 calc R . .
C5 C -0.17646(17) 0.1406(3) 0.4880(3) 0.0465(8) Uani 1 1 d . . .
H5 H -0.1955 0.0650 0.4343 0.080 Uiso 1 1 calc R . .
C6 C -0.22790(16) 0.2543(3) 0.5149(2) 0.0408(7) Uani 1 1 d . . .
N7 N -0.30600(14) 0.2660(2) 0.4624(2) 0.0548(7) Uani 1 1 d . . .
N8 N -0.34863(15) 0.1462(2) 0.4208(2) 0.0510(7) Uani 1 1 d . . .
C9 C -0.42423(18) 0.1821(3) 0.3968(3) 0.0509(8) Uani 1 1 d . . .
C10 C -0.44227(19) 0.3331(3) 0.4203(3) 0.0776(11) Uani 1 1 d . . .
H10A H -0.4875 0.3436 0.4789 0.080 Uiso 1 1 calc R . .
H10B H -0.4566 0.3808 0.3426 0.080 Uiso 1 1 calc R . .
C11 C -0.36083(17) 0.3913(3) 0.4765(3) 0.0568(8) Uani 1 1 d . . .
C12 C -0.32691(16) 0.5155(3) 0.4026(3) 0.0490(8) Uani 1 1 d . . .
C13 C -0.33594(17) 0.6518(3) 0.4475(3) 0.0550(8) Uani 1 1 d . . .
H13 H -0.3612 0.6678 0.5287 0.080 Uiso 1 1 calc R . .
C14 C -0.3087(2) 0.7658(3) 0.3758(4) 0.0704(10) Uani 1 1 d . . .
H14 H -0.3152 0.8601 0.4078 0.080 Uiso 1 1 calc R . .
C15 C -0.2729(2) 0.7451(4) 0.2606(4) 0.0742(10) Uani 1 1 d . . .
H15 H -0.2534 0.8242 0.2120 0.080 Uiso 1 1 calc R . .
C16 C -0.2649(2) 0.6116(5) 0.2152(3) 0.0764(11) Uani 1 1 d . . .
H16 H -0.2404 0.5968 0.1333 0.080 Uiso 1 1 calc R . .
C17 C -0.29144(19) 0.4973(3) 0.2846(3) 0.0640(9) Uani 1 1 d . . .
H17 H -0.2853 0.4037 0.2507 0.080 Uiso 1 1 calc R . .
O18 O -0.37516(13) 0.4218(3) 0.6049(2) 0.0715(8) Uani 1 1 d . . .
H18X H -0.331(2) 0.436(4) 0.634(3) 0.080 Uiso 1 1 d . . .
C19 C -0.48843(19) 0.0832(3) 0.3479(3) 0.0732(10) Uani 1 1 d . . .
H19A H -0.4637 -0.0082 0.3351 0.080 Uiso 1 1 calc R . .
H19B H -0.5103 0.1179 0.2688 0.080 Uiso 1 1 calc R . .
H19C H -0.5329 0.0756 0.4082 0.080 Uiso 1 1 calc R . .
S20 S 0.03011(4) 0.25518(8) 0.67961(7) 0.0512(3) Uani 1 1 d . . .
O21 O 0.06891(13) 0.1219(2) 0.6575(2) 0.0780(7) Uani 1 1 d . . .
O22 O 0.02806(13) 0.3069(3) 0.8059(2) 0.0930(8) Uani 1 1 d . . .
C23 C 0.07959(19) 0.3794(4) 0.5852(3) 0.0800(11) Uani 1 1 d . . .
H23A H 0.1381 0.3822 0.6064 0.080 Uiso 1 1 calc R . .
H23B H 0.0553 0.4708 0.5994 0.080 Uiso 1 1 calc R . .
H23C H 0.0728 0.3539 0.4975 0.080 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0371(16) 0.0451(15) 0.0593(16) -0.0052(13) -0.0107(12) 0.0034(12)
C2 0.0425(19) 0.0481(19) 0.0502(18) -0.0014(14) -0.0076(15) -0.0008(16)
C3 0.0369(17) 0.0448(18) 0.0451(18) 0.0035(14) -0.0048(14) 0.0012(15)
C4 0.041(2) 0.0458(19) 0.065(2) -0.0016(16) -0.0044(15) 0.0056(15)
C5 0.0400(19) 0.0446(19) 0.0548(19) -0.0052(14) -0.0066(15) 0.0020(16)
C6 0.0328(18) 0.0427(19) 0.0468(18) 0.0038(15) -0.0057(14) -0.0002(15)
N7 0.0378(17) 0.0387(15) 0.088(2) -0.0048(13) -0.0207(14) 0.0005(12)
N8 0.0422(17) 0.0530(17) 0.0575(16) -0.0013(12) -0.0099(12) -0.0055(13)
C9 0.039(2) 0.061(2) 0.0526(19) 0.0001(15) -0.0077(15) -0.0071(17)
C10 0.046(2) 0.067(2) 0.119(3) 0.003(2) -0.024(2) -0.0027(18)
C11 0.0364(19) 0.054(2) 0.079(3) -0.0057(19) -0.0124(16) 0.0074(16)
C12 0.0395(18) 0.045(2) 0.062(2) -0.0063(17) -0.0192(15) 0.0076(15)
C13 0.0415(19) 0.054(2) 0.069(2) -0.0109(19) -0.0143(15) 0.0058(16)
C14 0.064(2) 0.050(2) 0.097(3) -0.008(2) -0.029(2) 0.0069(19)
C15 0.076(3) 0.068(3) 0.078(3) 0.015(2) -0.026(2) 0.001(2)
C16 0.091(3) 0.082(3) 0.056(2) 0.005(2) -0.0135(19) 0.012(2)
C17 0.073(2) 0.053(2) 0.066(2) -0.0106(19) -0.0161(19) 0.0132(18)
O18 0.0515(15) 0.0846(17) 0.0784(18) 0.0008(13) 0.0048(13) 0.0068(13)
C19 0.053(2) 0.085(3) 0.081(2) -0.0096(19) -0.0130(18) -0.0123(18)
S20 0.0413(5) 0.0567(6) 0.0553(6) 0.0056(4) -0.0139(4) 0.0052(4)
O21 0.0546(14) 0.0509(13) 0.128(2) 0.0018(13) -0.0324(13) 0.0154(11)
O22 0.0641(16) 0.159(2) 0.0556(15) -0.0256(15) -0.0194(11) 0.0161(15)
C23 0.050(2) 0.086(2) 0.104(3) 0.031(2) -0.0244(19) -0.0157(19)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s.
planes)
are estimated using the full covariance matrix. The cell esds are
taken
into account individually in the estimation of esds in distances,
angles
and torsion angles; correlations between esds in cell parameters are
only
used when they are defined by crystal symmetry. An approximate
(isotropic)
treatment of cell esds is used for estimating esds involving l.s.
planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.336(3) . ?
N1 C6 1.340(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.385(4) . ?
C3 S20 1.756(3) . ?
C4 C5 1.363(4) . ?
C5 C6 1.384(3) . ?
C6 N7 1.366(3) . ?
N7 N8 1.391(3) . ?
N7 C11 1.482(3) . ?
N8 C9 1.278(3) . ?
C9 C19 1.478(4) . ?
C9 C10 1.478(4) . ?
C10 C11 1.528(4) . ?
C11 O18 1.404(4) . ?
C11 C12 1.512(4) . ?
C12 C13 1.381(4) . ?
C12 C17 1.381(4) . ?
C13 C14 1.388(4) . ?
C14 C15 1.359(4) . ?
C15 C16 1.357(5) . ?
C16 C17 1.374(4) . ?
S20 O22 1.417(2) . ?
S20 O21 1.424(2) . ?
S20 C23 1.734(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 117.5(2) . . ?
N1 C2 C3 123.0(3) . . ?
C2 C3 C4 118.2(3) . . ?
C2 C3 S20 120.5(2) . . ?
C4 C3 S20 121.2(2) . . ?
C5 C4 C3 119.8(3) . . ?
C4 C5 C6 118.2(3) . . ?
N1 C6 N7 115.2(2) . . ?
N1 C6 C5 123.2(2) . . ?
N7 C6 C5 121.5(2) . . ?
C6 N7 N8 120.3(2) . . ?
C6 N7 C11 124.3(2) . . ?
N8 N7 C11 113.2(2) . . ?
C9 N8 N7 107.8(2) . . ?
N8 C9 C19 123.6(3) . . ?
N8 C9 C10 114.1(2) . . ?
C19 C9 C10 122.3(3) . . ?
C9 C10 C11 104.3(2) . . ?
O18 C11 N7 111.2(2) . . ?
O18 C11 C12 113.5(2) . . ?
N7 C11 C12 110.8(2) . . ?
O18 C11 C10 107.6(3) . . ?
N7 C11 C10 100.1(2) . . ?
C12 C11 C10 112.8(3) . . ?
C13 C12 C17 118.0(3) . . ?
C13 C12 C11 120.6(3) . . ?
C17 C12 C11 121.2(3) . . ?
C12 C13 C14 120.3(3) . . ?
C15 C14 C13 120.7(3) . . ?
C16 C15 C14 119.3(3) . . ?
C15 C16 C17 120.9(3) . . ?
C16 C17 C12 120.8(3) . . ?
O22 S20 O21 118.18(15) . . ?
O22 S20 C23 108.56(18) . . ?
O21 S20 C23 107.71(16) . . ?
O22 S20 C3 109.49(13) . . ?
O21 S20 C3 108.33(13) . . ?
C23 S20 C3 103.59(13) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        20.82
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.038

data_f876
_database_code_depnum_ccdc_archive 'CCDC 263089'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 F3 N3 O3 S'
_chemical_formula_weight         385.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3741(5)
_cell_length_b                   19.8459(13)
_cell_length_c                   10.4665(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.8450(10)
_cell_angle_gamma                90.00
_cell_volume                     1646.20(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       PRISM
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8453
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         20.81
_reflns_number_total             1721
_reflns_number_gt                1463
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR
and
goodness of fit S are based on F^2^, conventional R-factors R are
based
on F, with F set to zero for negative F^2^. The threshold expression
of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc.
and is
not relevant to the choice of reflections for refinement. R-factors
based
on F^2^ are statistically about twice as large as those based on F,
and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+0.0000P] where
P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1721
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0788
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0423(2) 0.04611(9) 0.26259(19) 0.0445(5) Uani 1 1 d . . .
C2 C 0.1007(3) 0.10379(12) 0.3271(2) 0.0443(7) Uani 1 1 d . . .
H2 H 0.2100 0.1037 0.3949 0.080 Uiso 1 1 calc R . .
C3 C 0.0117(3) 0.16322(11) 0.3010(2) 0.0397(6) Uani 1 1 d . . .
C4 C -0.1463(3) 0.16385(12) 0.2014(2) 0.0444(7) Uani 1 1 d . . .
H4 H -0.2114 0.2046 0.1817 0.080 Uiso 1 1 calc R . .
C5 C -0.2075(3) 0.10610(12) 0.1322(2) 0.0432(6) Uani 1 1 d . . .
H5 H -0.3142 0.1055 0.0612 0.080 Uiso 1 1 calc R . .
C6 C -0.1099(3) 0.04791(12) 0.1682(2) 0.0388(6) Uani 1 1 d . . .
N7 N -0.1691(2) -0.01294(9) 0.10776(19) 0.0443(5) Uani 1 1 d . . .
C8 C -0.0885(3) -0.07886(11) 0.1440(2) 0.0429(6) Uani 1 1 d . . .
C9 C -0.1806(3) -0.12096(12) 0.0206(2) 0.0505(7) Uani 1 1 d . . .
H9A H -0.1042 -0.1370 -0.0240 0.080 Uiso 1 1 calc R . .
H9B H -0.2364 -0.1587 0.0448 0.080 Uiso 1 1 calc R . .
C10 C -0.3056(3) -0.07232(13) -0.0669(2) 0.0423(7) Uani 1 1 d . . .
N11 N -0.2959(2) -0.01295(10) -0.0163(2) 0.0444(5) Uani 1 1 d . . .
C12 C -0.4251(3) -0.08857(13) -0.1999(2) 0.0454(7) Uani 1 1 d . . .
C13 C -0.5106(3) -0.03803(14) -0.2866(3) 0.0600(8) Uani 1 1 d . . .
H13 H -0.4913 0.0083 -0.2597 0.080 Uiso 1 1 calc R . .
C14 C -0.6233(4) -0.05428(18) -0.4113(3) 0.0772(9) Uani 1 1 d . . .
H14 H -0.6839 -0.0191 -0.4701 0.080 Uiso 1 1 calc R . .
C15 C -0.6493(4) -0.11989(19) -0.4519(3) 0.0753(9) Uani 1 1 d . . .
H15 H -0.7259 -0.1307 -0.5398 0.080 Uiso 1 1 calc R . .
C16 C -0.5667(4) -0.17001(16) -0.3676(3) 0.0680(8) Uani 1 1 d . . .
H16 H -0.5859 -0.2161 -0.3960 0.080 Uiso 1 1 calc R . .
C17 C -0.4554(3) -0.15491(13) -0.2417(3) 0.0542(7) Uani 1 1 d . . .
H17 H -0.3985 -0.1906 -0.1827 0.080 Uiso 1 1 calc R . .
C18 C -0.1235(4) -0.10612(14) 0.2676(3) 0.0572(8) Uani 1 1 d . . .
F19 F -0.0528(2) -0.07027(8) 0.37946(16) 0.0800(5) Uani 1 1 d . . .
F20 F -0.0652(2) -0.16897(8) 0.29402(16) 0.0831(5) Uani 1 1 d . . .
F21 F -0.2879(2) -0.10806(8) 0.24977(16) 0.0785(5) Uani 1 1 d . . .
O22 O 0.0848(2) -0.07830(9) 0.16710(19) 0.0577(5) Uani 1 1 d . . .
H22X H 0.120(4) -0.0455(14) 0.216(3) 0.080 Uiso 1 1 d . . .
S23 S 0.09494(9) 0.23627(3) 0.39127(6) 0.0508(3) Uani 1 1 d . . .
O24 O 0.2553(2) 0.21935(9) 0.48684(17) 0.0666(6) Uani 1 1 d . . .
O25 O -0.0296(2) 0.26619(8) 0.43990(17) 0.0654(5) Uani 1 1 d . . .
C26 C 0.1274(4) 0.29077(13) 0.2713(3) 0.0663(8) Uani 1 1 d . . .
H26A H 0.0221 0.2988 0.2014 0.080 Uiso 1 1 calc R . .
H26B H 0.2059 0.2708 0.2328 0.080 Uiso 1 1 calc R . .
H26C H 0.1720 0.3327 0.3136 0.080 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0436(13) 0.0367(13) 0.0498(13) -0.0004(11) 0.0104(11) 0.0026(11)
C2 0.0453(16) 0.0434(17) 0.0425(15) 0.0001(13) 0.0119(12) 0.0004(14)
C3 0.0488(16) 0.0344(15) 0.0383(15) 0.0011(12) 0.0172(13) 0.0020(13)
C4 0.0533(18) 0.0380(16) 0.0432(15) 0.0052(13) 0.0176(14) 0.0068(13)
C5 0.0483(16) 0.0352(16) 0.0462(15) 0.0039(13) 0.0154(13) 0.0049(13)
C6 0.0427(16) 0.0352(16) 0.0406(15) 0.0020(13) 0.0165(13) -0.0023(14)
N7 0.0475(13) 0.0314(13) 0.0484(14) 0.0035(10) 0.0077(11) 0.0037(11)
C8 0.0450(17) 0.0328(15) 0.0510(17) 0.0043(12) 0.0155(13) -0.0008(13)
C9 0.0574(17) 0.0391(15) 0.0550(17) -0.0009(14) 0.0182(14) 0.0004(14)
C10 0.0416(16) 0.0391(17) 0.0502(17) 0.0014(13) 0.0205(14) -0.0021(13)
N11 0.0423(13) 0.0411(14) 0.0479(13) 0.0004(11) 0.0119(11) -0.0013(11)
C12 0.0418(16) 0.0483(17) 0.0487(17) -0.0006(15) 0.0183(14) 0.0012(14)
C13 0.0651(19) 0.0549(18) 0.0563(19) -0.0015(16) 0.0143(16) -0.0005(16)
C14 0.081(2) 0.081(3) 0.057(2) 0.0069(18) 0.0050(18) 0.0149(19)
C15 0.073(2) 0.086(3) 0.057(2) -0.016(2) 0.0076(17) 0.002(2)
C16 0.064(2) 0.066(2) 0.072(2) -0.0224(19) 0.0191(18) -0.0012(18)
C17 0.0530(17) 0.0496(19) 0.060(2) -0.0085(14) 0.0185(16) -0.0020(14)
C18 0.066(2) 0.0463(19) 0.058(2) 0.0019(16) 0.0186(16) -0.0033(16)
F19 0.1143(14) 0.0720(11) 0.0523(10) -0.0002(9) 0.0251(10) -0.0166(10)
F20 0.1161(14) 0.0474(10) 0.0808(12) 0.0228(9) 0.0250(10) 0.0086(10)
F21 0.0782(13) 0.0791(12) 0.0917(13) 0.0051(9) 0.0461(10) -0.0105(10)
O22 0.0448(12) 0.0481(12) 0.0791(14) -0.0062(9) 0.0186(10) 0.0040(10)
S23 0.0620(5) 0.0404(4) 0.0470(4) -0.0061(3) 0.0137(4) 0.0022(4)
O24 0.0665(13) 0.0582(12) 0.0560(11) -0.0126(9) -0.0067(10) 0.0071(10)
O25 0.0809(13) 0.0561(12) 0.0660(13) -0.0106(9) 0.0333(11) 0.0149(10)
C26 0.078(2) 0.0452(17) 0.076(2) -0.0024(15) 0.0255(17) -0.0112(15)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s.
planes)
are estimated using the full covariance matrix. The cell esds are
taken
into account individually in the estimation of esds in distances,
angles
and torsion angles; correlations between esds in cell parameters are
only
used when they are defined by crystal symmetry. An approximate
(isotropic)
treatment of cell esds is used for estimating esds involving l.s.
planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.338(3) . ?
N1 C2 1.339(3) . ?
C2 C3 1.375(3) . ?
C3 C4 1.395(3) . ?
C3 S23 1.748(2) . ?
C4 C5 1.364(3) . ?
C5 C6 1.394(3) . ?
C6 N7 1.379(3) . ?
N7 N11 1.387(2) . ?
N7 C8 1.465(3) . ?
C8 O22 1.392(3) . ?
C8 C18 1.515(3) . ?
C8 C9 1.522(3) . ?
C9 C10 1.499(3) . ?
C10 N11 1.284(3) . ?
C10 C12 1.464(3) . ?
C12 C17 1.385(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.380(4) . ?
C14 C15 1.365(4) . ?
C15 C16 1.361(4) . ?
C16 C17 1.379(3) . ?
C18 F21 1.329(3) . ?
C18 F19 1.334(3) . ?
C18 F20 1.335(3) . ?
S23 O25 1.4289(17) . ?
S23 O24 1.4314(17) . ?
S23 C26 1.744(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 117.1(2) . . ?
N1 C2 C3 123.2(2) . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 S23 120.53(19) . . ?
C4 C3 S23 120.86(19) . . ?
C5 C4 C3 119.5(2) . . ?
C4 C5 C6 117.7(2) . . ?
N1 C6 N7 115.5(2) . . ?
N1 C6 C5 123.9(2) . . ?
N7 C6 C5 120.6(2) . . ?
C6 N7 N11 118.84(19) . . ?
C6 N7 C8 126.62(19) . . ?
N11 N7 C8 113.07(18) . . ?
O22 C8 N7 113.88(18) . . ?
O22 C8 C18 109.4(2) . . ?
N7 C8 C18 109.9(2) . . ?
O22 C8 C9 111.44(19) . . ?
N7 C8 C9 101.88(18) . . ?
C18 C8 C9 110.1(2) . . ?
C10 C9 C8 103.13(19) . . ?
N11 C10 C12 121.8(2) . . ?
N11 C10 C9 113.6(2) . . ?
C12 C10 C9 124.5(2) . . ?
C10 N11 N7 108.27(19) . . ?
C17 C12 C13 118.6(2) . . ?
C17 C12 C10 120.6(2) . . ?
C13 C12 C10 120.8(2) . . ?
C14 C13 C12 120.1(3) . . ?
C15 C14 C13 120.6(3) . . ?
C16 C15 C14 119.9(3) . . ?
C15 C16 C17 120.4(3) . . ?
C16 C17 C12 120.5(3) . . ?
F21 C18 F19 106.5(2) . . ?
F21 C18 F20 107.1(2) . . ?
F19 C18 F20 106.7(2) . . ?
F21 C18 C8 111.6(2) . . ?
F19 C18 C8 113.9(2) . . ?
F20 C18 C8 110.6(2) . . ?
O25 S23 O24 118.45(11) . . ?
O25 S23 C26 107.46(13) . . ?
O24 S23 C26 108.64(13) . . ?
O25 S23 C3 109.12(11) . . ?
O24 S23 C3 107.67(11) . . ?
C26 S23 C3 104.65(12) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        20.81
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.030

data_f888
_database_code_depnum_ccdc_archive 'CCDC 263090'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 F3 N2'
_chemical_formula_weight         288.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4600(10)
_cell_length_b                   16.282(2)
_cell_length_c                   10.7060(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.520(10)
_cell_angle_gamma                90.00
_cell_volume                     1406.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    31
_cell_measurement_theta_min      11.783
_cell_measurement_theta_max      49.795

_exptl_crystal_description       prisms
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'theta and 2theta scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1570
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.11
_diffrn_reflns_theta_max         50.00
_reflns_number_total             1449
_reflns_number_gt                978
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR
and
goodness of fit S are based on F^2^, conventional R-factors R are
based
on F, with F set to zero for negative F^2^. The threshold expression
of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc.
and is
not relevant to the choice of reflections for refinement. R-factors
based
on F^2^ are statistically about twice as large as those based on F,
and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w=1/[\s^2^(Fo^2^)+(0.0771P)^2^+0.0000P] where
P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0041(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1449
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0597(4) 0.88616(18) 0.4291(3) 0.0505(8) Uani 1 1 d . . .
N2 N 0.0349(4) 0.92848(18) 0.3150(3) 0.0556(9) Uani 1 1 d . . .
C3 C -0.1159(5) 0.9062(2) 0.2446(3) 0.0557(10) Uani 1 1 d . . .
C4 C -0.1880(5) 0.8512(2) 0.3092(3) 0.0554(11) Uani 1 1 d . . .
H4A H -0.2927 0.8276 0.2781 0.080 Uiso 1 1 calc R . .
C5 C -0.0728(5) 0.8386(2) 0.4292(3) 0.0489(10) Uani 1 1 d . . .
C6 C -0.0902(4) 0.7918(2) 0.5411(3) 0.0485(10) Uani 1 1 d . . .
C7 C -0.1554(5) 0.7136(2) 0.5227(4) 0.0626(11) Uani 1 1 d . . .
H7A H -0.1827 0.6899 0.4399 0.080 Uiso 1 1 calc R . .
C8 C -0.1807(5) 0.6700(3) 0.6251(5) 0.0745(13) Uani 1 1 d . . .
H8A H -0.2253 0.6173 0.6112 0.080 Uiso 1 1 calc R . .
C9 C -0.1404(5) 0.7038(3) 0.7468(4) 0.0736(13) Uani 1 1 d . . .
H9A H -0.1564 0.6742 0.8162 0.080 Uiso 1 1 calc R . .
C10 C -0.0758(5) 0.7822(3) 0.7672(4) 0.0679(12) Uani 1 1 d . . .
H10A H -0.0489 0.8053 0.8503 0.080 Uiso 1 1 calc R . .
C11 C -0.0511(5) 0.8261(2) 0.6652(4) 0.0580(11) Uani 1 1 d . . .
H11A H -0.0080 0.8790 0.6795 0.080 Uiso 1 1 calc R . .
C12 C -0.1874(8) 0.9416(4) 0.1117(5) 0.0784(14) Uani 1 1 d . . .
F13 F -0.3471(11) 0.9336(13) 0.0693(12) 0.138(8) Uani 0.66(3) 1 d P . .
F14 F -0.158(2) 1.0199(5) 0.1059(8) 0.117(5) Uani 0.66(3) 1 d P . .
F15 F -0.1248(18) 0.9064(9) 0.0274(7) 0.122(6) Uani 0.66(3) 1 d P . .
F13A F -0.287(8) 0.893(2) 0.037(3) 0.24(2) Uani 0.34(3) 1 d P . .
F14A F -0.276(7) 1.005(3) 0.110(2) 0.170(18) Uani 0.34(3) 1 d P . .
F15A F -0.086(3) 0.967(4) 0.055(4) 0.22(2) Uani 0.34(3) 1 d P . .
C16 C 0.2199(5) 0.8910(2) 0.5256(3) 0.0518(10) Uani 1 1 d . . .
C17 C 0.3013(5) 0.8208(3) 0.5804(4) 0.0680(12) Uani 1 1 d . . .
H17A H 0.2522 0.7697 0.5576 0.080 Uiso 1 1 calc R . .
C18 C 0.4569(6) 0.8272(4) 0.6695(5) 0.0901(16) Uani 1 1 d . . .
H18A H 0.5131 0.7800 0.7078 0.080 Uiso 1 1 calc R . .
C19 C 0.5289(6) 0.9022(4) 0.7019(5) 0.0981(17) Uani 1 1 d . . .
H19A H 0.6337 0.9062 0.7626 0.080 Uiso 1 1 calc R . .
C20 C 0.4475(7) 0.9710(3) 0.6456(5) 0.0994(17) Uani 1 1 d . . .
H20A H 0.4973 1.0221 0.6674 0.080 Uiso 1 1 calc R . .
C21 C 0.2917(5) 0.9658(3) 0.5563(4) 0.0757(13) Uani 1 1 d . . .
H21A H 0.2365 1.0130 0.5175 0.080 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.052(2) 0.0524(19) 0.0462(19) 0.0018(16) 0.0130(16) 0.0031(17)
N2 0.066(2) 0.056(2) 0.046(2) 0.0060(17) 0.0178(18) -0.0006(17)
C3 0.061(3) 0.056(3) 0.045(2) 0.004(2) 0.010(2) 0.002(2)
C4 0.061(3) 0.054(2) 0.050(2) -0.0004(19) 0.014(2) -0.006(2)
C5 0.053(2) 0.046(2) 0.047(2) -0.0018(19) 0.014(2) 0.002(2)
C6 0.050(2) 0.048(2) 0.047(2) 0.000(2) 0.0145(18) 0.0038(19)
C7 0.070(3) 0.062(3) 0.055(3) 0.001(2) 0.017(2) -0.004(2)
C8 0.076(3) 0.071(3) 0.077(3) 0.011(3) 0.024(3) -0.006(2)
C9 0.067(3) 0.092(4) 0.069(3) 0.027(3) 0.032(2) 0.009(3)
C10 0.066(3) 0.091(3) 0.049(2) -0.001(3) 0.021(2) 0.011(3)
C11 0.061(3) 0.058(2) 0.057(3) -0.003(2) 0.021(2) -0.001(2)
C12 0.086(4) 0.081(4) 0.060(4) 0.007(3) 0.009(4) -0.004(4)
F13 0.076(6) 0.215(19) 0.099(7) 0.073(9) -0.010(4) -0.021(7)
F14 0.178(12) 0.077(5) 0.071(5) 0.025(4) 0.000(6) -0.015(7)
F15 0.188(12) 0.138(8) 0.046(4) 0.002(5) 0.042(4) 0.035(7)
F13A 0.37(5) 0.16(2) 0.075(13) 0.053(13) -0.11(2) -0.12(3)
F14A 0.21(4) 0.18(3) 0.126(14) 0.084(17) 0.06(2) 0.11(3)
F15A 0.150(15) 0.35(5) 0.19(3) 0.20(3) 0.090(19) 0.05(3)
C16 0.050(3) 0.059(3) 0.047(2) 0.000(2) 0.016(2) 0.004(2)
C17 0.061(3) 0.070(3) 0.072(3) 0.015(2) 0.020(2) 0.010(2)
C18 0.060(3) 0.118(5) 0.088(3) 0.033(3) 0.015(3) 0.021(3)
C19 0.054(3) 0.153(6) 0.076(3) 0.003(4) 0.003(3) 0.002(4)
C20 0.077(4) 0.099(4) 0.111(4) -0.027(3) 0.010(3) -0.012(3)
C21 0.059(3) 0.073(3) 0.085(3) -0.014(2) 0.008(3) 0.002(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s.
planes)
are estimated using the full covariance matrix. The cell esds are
taken
into account individually in the estimation of esds in distances,
angles
and torsion angles; correlations between esds in cell parameters are
only
used when they are defined by crystal symmetry. An approximate
(isotropic)
treatment of cell esds is used for estimating esds involving l.s.
planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.362(4) . ?
N1 N2 1.363(4) . ?
N1 C16 1.438(4) . ?
N2 C3 1.322(4) . ?
C3 C4 1.381(5) . ?
C3 C12 1.484(6) . ?
C4 C5 1.374(5) . ?
C5 C6 1.465(5) . ?
C6 C7 1.378(5) . ?
C6 C11 1.386(5) . ?
C7 C8 1.376(5) . ?
C8 C9 1.360(6) . ?
C9 C10 1.379(6) . ?
C10 C11 1.372(5) . ?
C12 F13 1.296(11) . ?
C12 F15A 1.26(2) . ?
C12 F14A 1.27(2) . ?
C12 F13A 1.26(2) . ?
C12 F15 1.309(11) . ?
C12 F14 1.304(10) . ?
F13 F13A 0.96(6) . ?
F13 F14A 1.33(4) . ?
F14 F14A 1.03(4) . ?
F14 F15A 1.27(5) . ?
F15 F15A 1.05(6) . ?
F15 F13A 1.42(6) . ?
C16 C21 1.356(5) . ?
C16 C17 1.372(5) . ?
C17 C18 1.378(6) . ?
C18 C19 1.362(7) . ?
C19 C20 1.358(7) . ?
C20 C21 1.379(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 N2 112.5(3) . . ?
C5 N1 C16 129.0(3) . . ?
N2 N1 C16 118.3(3) . . ?
C3 N2 N1 103.6(3) . . ?
N2 C3 C4 112.8(3) . . ?
N2 C3 C12 119.0(4) . . ?
C4 C3 C12 128.1(4) . . ?
C5 C4 C3 105.6(3) . . ?
N1 C5 C4 105.5(3) . . ?
N1 C5 C6 125.5(3) . . ?
C4 C5 C6 128.7(4) . . ?
C7 C6 C11 118.6(3) . . ?
C7 C6 C5 119.9(3) . . ?
C11 C6 C5 121.4(3) . . ?
C8 C7 C6 121.0(4) . . ?
C9 C8 C7 120.0(4) . . ?
C8 C9 C10 120.0(4) . . ?
C11 C10 C9 120.3(4) . . ?
C10 C11 C6 120.2(4) . . ?
F13 C12 F15A 130.7(16) . . ?
F13 C12 F14A 62(2) . . ?
F15A C12 F14A 102.0(16) . . ?
F13 C12 F13A 44(3) . . ?
F15A C12 F13A 109(2) . . ?
F14A C12 F13A 103(2) . . ?
F13 C12 F15 108.1(9) . . ?
F15A C12 F15 48(3) . . ?
F14A C12 F15 134.7(9) . . ?
F13A C12 F15 67(3) . . ?
F13 C12 F14 105.9(9) . . ?
F15A C12 F14 60(2) . . ?
F14A C12 F14 47(2) . . ?
F13A C12 F14 133.4(13) . . ?
F15 C12 F14 105.9(8) . . ?
F13 C12 C3 112.2(7) . . ?
F15A C12 C3 116.7(12) . . ?
F14A C12 C3 113.4(10) . . ?
F13A C12 C3 111.7(12) . . ?
F15 C12 C3 111.0(6) . . ?
F14 C12 C3 113.4(5) . . ?
F13A F13 C12 66(2) . . ?
F13A F13 F14A 119(3) . . ?
C12 F13 F14A 58.2(12) . . ?
F14A F14 C12 64.9(16) . . ?
F14A F14 F15A 117(2) . . ?
C12 F14 F15A 58.5(15) . . ?
F15A F15 C12 63.5(19) . . ?
F15A F15 F13A 111(2) . . ?
C12 F15 F13A 54.5(16) . . ?
F13 F13A C12 70(2) . . ?
F13 F13A F15 123(3) . . ?
C12 F13A F15 58(2) . . ?
F14 F14A C12 67.9(18) . . ?
F14 F14A F13 122(2) . . ?
C12 F14A F13 59.7(16) . . ?
F15 F15A C12 68(2) . . ?
F15 F15A F14 127(3) . . ?
C12 F15A F14 61.9(17) . . ?
C21 C16 C17 120.9(4) . . ?
C21 C16 N1 118.7(4) . . ?
C17 C16 N1 120.3(4) . . ?
C16 C17 C18 119.1(4) . . ?
C19 C18 C17 120.3(5) . . ?
C20 C19 C18 119.9(5) . . ?
C19 C20 C21 120.6(5) . . ?
C16 C21 C20 119.2(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        50.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.033