Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2005
data_global
_journal_coden_Cambridge 177
loop_
_publ_author_name
'Wei Zhuang.'
'Rita G. Hazell'
'Karl Anker Jorgensen'
_publ_contact_author_name 'Karl Anker Jorgensen'
_publ_contact_author_address
;
Department of Chemistry
Aarhus University
Aarhus C
DK 8000
DENMARK
;
_publ_contact_author_email KAJ@CHEM.AU.DK
_publ_requested_journal 'Organic & Biomolecular Chemistry'
_publ_section_title
;
Enantioselective Friedel-Crafts type addition of
indoles to nitroolefins using a chiral hydrogen-bonding catalyst -
synthesis of optically active tetrahydro-beta-carbolines
;
#==============================================================================
_publ_section_references
;
Becker,P.J. & Coppens, P. (1974). Acta Cryst. A30, 129-153.
Burnett,M.N. & Johnson,C.K. (1996). ORTEP-III. Report ORNL-6895.
Oak Ridge National Laboratory, Tennessee, USA.
Busing,W.R., Martin,K.O. & Levy,H.A. (1962). ORFLS. Report
ORNL-TM-305. Oak Ridge National Laboratory, Tennessee, USA.
Hazell,A. (1995). KRYSTAL, An integrated system of
crystallographic programs. Aarhus University, Denmark.
Rogers,D. (1981). Acta Cryst. A37, 734-741.
Siemens (1995) SMART, SAINT and XPREP Area-Detector Control and
Integration Software. Siemens Analytical X-ray Instruments Inc.
Madison, Wisconsin, USA.
;
data_04jowz002_0m
_database_code_depnum_ccdc_archive 'CCDC 268882'
_audit_creation_date 2005-01-24T10:45:59-00:00
_audit_creation_method 'WinGX routine CIF_UPDATE'
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C31 H25 Cl1 N2 O1'
_chemical_formula_sum 'C31 H25 Cl N2 O'
_chemical_formula_weight 476.98
_chemical_compound_source 'synthesis as described'
_chemical_absolute_configuration ad
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting trigonal
_symmetry_space_group_name_H-M 'P 31'
_symmetry_space_group_name_Hall 'P 31'
_symmetry_Int_Tables_number 144
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
_cell_length_a 10.0175(8)
_cell_length_b 10.0175(8)
_cell_length_c 21.2378(13)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 120
_cell_volume 1845.7(2)
_cell_formula_units_Z 3
_cell_measurement_temperature 225(2)
_cell_measurement_reflns_used 1904
_cell_measurement_theta_min 2.35
_cell_measurement_theta_max 20.57
_cell_measurement_wavelength 0.71073
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description prism
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.08
_exptl_crystal_density_diffrn 1.287
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 750
_exptl_special_details
;
?
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu 0.182
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_correction_T_min 0.955
_exptl_absorpt_correction_T_max 0.988
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature 225(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_measurement_device_type 'Bruker APEX2 CCD-based diffractometer'
_diffrn_measurement_method \f-scans
_diffrn_detector_area_resol_mean 0.0833
_diffrn_standards_number 0
_diffrn_reflns_av_R_equivalents 0.0486
_diffrn_reflns_av_unetI/netI 0.0764
_diffrn_reflns_number 4167
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 26
_diffrn_reflns_theta_min 2.54
_diffrn_reflns_theta_max 25.94
_diffrn_reflns_theta_full 25.94
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total 4167
_reflns_number_gt 2774
_reflns_threshold_expression >2sigma(I)
_diffrn_reflns_reduction_process
;
Scaled and merged with SORTAV
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection 'Apex2 (Bruker-Nonius, 2004)'
_computing_cell_refinement 'SAINT+ (Bruker-Nonius, 2004)'
_computing_data_reduction 'SAINT+ (Bruker-Nonius, 2004)'
_computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'WinGX publication routines (Farrugia, 1999)'
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_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^)+(0.0414P)^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 constr
_refine_ls_extinction_method none
_refine_ls_number_reflns 4167
_refine_ls_number_parameters 316
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0761
_refine_ls_R_factor_gt 0.0387
_refine_ls_wR_factor_ref 0.0905
_refine_ls_wR_factor_gt 0.0805
_refine_ls_goodness_of_fit_ref 0.962
_refine_ls_restrained_S_all 0.961
_refine_ls_shift/su_max 0
_refine_ls_shift/su_mean 0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.03(6)
_refine_diff_density_max 0.139
_refine_diff_density_min -0.17
_refine_diff_density_rms 0.034
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
Cl1 Cl -0.25431(9) 0.14116(9) 0.31830(4) 0.0589(2) Uani 1 1 d . . .
O1 O 0.1377(3) 0.6688(3) 0.54004(11) 0.0887(9) Uani 1 1 d . . .
N1 N 0.4943(3) 1.2088(3) 0.49649(9) 0.0396(6) Uani 1 1 d . . .
N2 N 0.2920(3) 0.7922(3) 0.45745(10) 0.0406(6) Uani 1 1 d . . .
C1 C 0.4209(3) 1.2349(3) 0.39872(11) 0.0360(7) Uani 1 1 d . . .
C2 C 0.4026(3) 1.3197(3) 0.35015(12) 0.0402(7) Uani 1 1 d . . .
H2 H 0.3553 1.271 0.3121 0.048 Uiso 1 1 calc R . .
C3 C 0.4538(4) 1.4731(3) 0.35842(14) 0.0456(8) Uani 1 1 d . . .
H3 H 0.4414 1.5294 0.3258 0.055 Uiso 1 1 calc R . .
C4 C 0.5247(4) 1.5480(4) 0.41487(14) 0.0479(8) Uani 1 1 d . . .
H4 H 0.5599 1.6538 0.4194 0.057 Uiso 1 1 calc R . .
C5 C 0.5431(3) 1.4687(4) 0.46354(13) 0.0431(7) Uani 1 1 d . . .
H5 H 0.5903 1.5186 0.5014 0.052 Uiso 1 1 calc R . .
C6 C 0.4900(3) 1.3123(3) 0.45524(12) 0.0363(7) Uani 1 1 d . . .
C7 C 0.4293(3) 1.0674(3) 0.46656(12) 0.0373(7) Uani 1 1 d . . .
C8 C 0.3867(3) 1.0792(3) 0.40667(12) 0.0357(7) Uani 1 1 d . . .
C9 C 0.3195(3) 0.9468(3) 0.36117(12) 0.0376(7) Uani 1 1 d . . .
H9 H 0.3864 0.9809 0.3234 0.045 Uiso 1 1 calc R . .
C9A C 0.1588(3) 0.9020(3) 0.33923(12) 0.0391(7) Uani 1 1 d . . .
C9B C 0.0551(4) 0.9162(4) 0.37710(15) 0.0522(8) Uani 1 1 d . . .
H9B H 0.0842 0.9538 0.4183 0.063 Uiso 1 1 calc R . .
C9C C -0.0911(4) 0.8767(4) 0.35612(18) 0.0648(10) Uani 1 1 d . . .
H9C H -0.16 0.8868 0.3831 0.078 Uiso 1 1 calc R . .
C9D C -0.1349(5) 0.8234(4) 0.2965(2) 0.0781(12) Uani 1 1 d . . .
H9D H -0.2334 0.798 0.2819 0.094 Uiso 1 1 calc R . .
C9E C -0.0337(5) 0.8070(4) 0.25766(19) 0.0788(13) Uani 1 1 d . . .
H9E H -0.0641 0.769 0.2166 0.095 Uiso 1 1 calc R . .
C9F C 0.1122(4) 0.8460(4) 0.27873(15) 0.0579(9) Uani 1 1 d . . .
H9F H 0.1801 0.8344 0.2518 0.069 Uiso 1 1 calc R . .
C10 C 0.3317(3) 0.8130(3) 0.38998(12) 0.0409(7) Uani 1 1 d . . .
H10A H 0.2623 0.7178 0.3674 0.049 Uiso 1 1 calc R . .
H10B H 0.4371 0.8326 0.3846 0.049 Uiso 1 1 calc R . .
C11 C 0.4004(3) 0.9216(3) 0.49791(12) 0.0405(7) Uani 1 1 d . . .
H11 H 0.3471 0.9133 0.5382 0.049 Uiso 1 1 calc R . .
C11A C 0.5429(4) 0.9093(3) 0.51288(12) 0.0413(7) Uani 1 1 d . . .
C11B C 0.6888(4) 1.0179(4) 0.49245(14) 0.0546(9) Uani 1 1 d . . .
H11B H 0.7026 1.1013 0.4674 0.065 Uiso 1 1 calc R . .
C11C C 0.8144(4) 1.0029(5) 0.50918(16) 0.0671(10) Uani 1 1 d . . .
H11C H 0.9134 1.0767 0.4953 0.081 Uiso 1 1 calc R . .
C11D C 0.7963(5) 0.8822(5) 0.54552(16) 0.0677(11) Uani 1 1 d . . .
H11D H 0.8823 0.8733 0.5567 0.081 Uiso 1 1 calc R . .
C11E C 0.6518(5) 0.7743(4) 0.56553(15) 0.0612(10) Uani 1 1 d . . .
H11E H 0.6389 0.6911 0.5905 0.073 Uiso 1 1 calc R . .
C11F C 0.5249(4) 0.7870(4) 0.54932(13) 0.0510(8) Uani 1 1 d . . .
H11F H 0.4262 0.7122 0.5631 0.061 Uiso 1 1 calc R . .
C12 C 0.1659(4) 0.6729(4) 0.48344(14) 0.0535(9) Uani 1 1 d . . .
C13 C 0.0621(4) 0.5406(4) 0.44138(14) 0.0488(8) Uani 1 1 d . . .
C14 C -0.0759(4) 0.5257(4) 0.42095(14) 0.0526(8) Uani 1 1 d . . .
H14 H -0.1034 0.5992 0.4326 0.063 Uiso 1 1 calc R . .
C15 C -0.1734(4) 0.4022(4) 0.38324(15) 0.0516(8) Uani 1 1 d . . .
H15 H -0.2667 0.3922 0.3688 0.062 Uiso 1 1 calc R . .
C16 C -0.1328(4) 0.2937(3) 0.36690(13) 0.0457(8) Uani 1 1 d . . .
C17 C 0.0031(4) 0.3058(4) 0.38765(14) 0.0506(8) Uani 1 1 d . . .
H17 H 0.0296 0.231 0.3767 0.061 Uiso 1 1 calc R . .
C18 C 0.0999(4) 0.4306(4) 0.42493(14) 0.0526(8) Uani 1 1 d . . .
H18 H 0.1932 0.4404 0.4393 0.063 Uiso 1 1 calc R . .
C20 C 0.5663(4) 1.2486(4) 0.55832(13) 0.0542(9) Uani 1 1 d . . .
H20A H 0.5338 1.1553 0.5826 0.081 Uiso 1 1 calc R . .
H20B H 0.5355 1.3142 0.58 0.081 Uiso 1 1 calc R . .
H20C H 0.6775 1.3029 0.5536 0.081 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
Cl1 0.0481(5) 0.0565(5) 0.0608(5) -0.0019(4) 0.0011(4) 0.0177(5)
O1 0.0792(19) 0.087(2) 0.0499(15) -0.0021(14) 0.0239(13) 0.0044(16)
N1 0.0444(15) 0.0417(15) 0.0358(12) -0.0071(11) -0.0066(11) 0.0237(12)
N2 0.0426(15) 0.0394(15) 0.0376(13) 0.0026(11) 0.0048(11) 0.0188(13)
C1 0.0295(15) 0.0402(18) 0.0349(15) 0.0016(13) 0.0017(12) 0.0148(14)
C2 0.0377(17) 0.0453(19) 0.0340(15) -0.0010(14) -0.0028(13) 0.0179(15)
C3 0.0481(19) 0.045(2) 0.0480(17) 0.0087(16) 0.0042(15) 0.0263(17)
C4 0.047(2) 0.0373(18) 0.0553(19) -0.0031(15) 0.0004(16) 0.0184(15)
C5 0.0413(18) 0.0438(19) 0.0407(15) -0.0040(14) -0.0041(14) 0.0187(15)
C6 0.0317(16) 0.0390(18) 0.0375(15) -0.0055(13) -0.0011(13) 0.0171(14)
C7 0.0351(17) 0.0417(18) 0.0363(14) -0.0040(14) -0.0023(13) 0.0202(15)
C8 0.0314(16) 0.0374(17) 0.0365(15) -0.0026(13) -0.0003(13) 0.0159(14)
C9 0.0360(17) 0.0383(16) 0.0335(14) -0.0033(13) 0.0008(13) 0.0147(14)
C9A 0.0425(18) 0.0305(16) 0.0371(15) -0.0002(13) -0.0052(14) 0.0128(15)
C9B 0.047(2) 0.053(2) 0.0530(18) -0.0042(16) -0.0067(16) 0.0217(18)
C9C 0.046(2) 0.057(2) 0.090(3) -0.006(2) -0.0130(19) 0.0239(18)
C9D 0.056(3) 0.062(3) 0.106(3) -0.002(2) -0.035(2) 0.022(2)
C9E 0.081(3) 0.065(3) 0.064(2) -0.014(2) -0.040(2) 0.017(2)
C9F 0.061(2) 0.050(2) 0.0503(19) -0.0076(16) -0.0133(17) 0.0183(18)
C10 0.0423(17) 0.0399(17) 0.0404(16) -0.0030(13) 0.0058(13) 0.0206(15)
C11 0.0425(18) 0.0436(18) 0.0322(14) -0.0032(13) 0.0000(13) 0.0190(15)
C11A 0.052(2) 0.0467(19) 0.0292(14) -0.0047(13) -0.0065(14) 0.0281(16)
C11B 0.055(2) 0.074(2) 0.0454(18) 0.0120(17) 0.0009(16) 0.041(2)
C11C 0.058(2) 0.090(3) 0.063(2) 0.008(2) -0.0003(18) 0.045(2)
C11D 0.082(3) 0.091(3) 0.058(2) -0.018(2) -0.027(2) 0.065(3)
C11E 0.093(3) 0.059(2) 0.0470(19) -0.0120(17) -0.025(2) 0.050(2)
C11F 0.070(2) 0.048(2) 0.0401(16) -0.0069(15) -0.0116(16) 0.0334(18)
C12 0.043(2) 0.056(2) 0.052(2) 0.0025(17) 0.0100(16) 0.0173(17)
C13 0.0414(19) 0.048(2) 0.0476(18) 0.0081(15) 0.0131(15) 0.0150(17)
C14 0.047(2) 0.048(2) 0.063(2) 0.0011(17) 0.0074(17) 0.0239(17)
C15 0.0401(19) 0.058(2) 0.0567(18) 0.0106(17) 0.0089(16) 0.0248(18)
C16 0.0396(18) 0.0443(19) 0.0454(17) 0.0058(14) 0.0053(14) 0.0151(16)
C17 0.050(2) 0.050(2) 0.0550(19) 0.0039(16) 0.0046(16) 0.0270(17)
C18 0.042(2) 0.057(2) 0.061(2) 0.0033(17) 0.0019(16) 0.0267(18)
C20 0.065(2) 0.057(2) 0.0401(16) -0.0105(16) -0.0172(16) 0.0304(19)
#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#
_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
Cl1 C16 1.738(3) . ?
O1 C12 1.231(3) . ?
N1 C6 1.374(4) . ?
N1 C7 1.383(3) . ?
N1 C20 1.455(3) . ?
N2 C12 1.349(4) . ?
N2 C10 1.474(3) . ?
N2 C11 1.480(3) . ?
C1 C2 1.405(4) . ?
C1 C6 1.408(4) . ?
C1 C8 1.429(4) . ?
C2 C3 1.366(4) . ?
C2 H2 0.94 . ?
C3 C4 1.404(4) . ?
C3 H3 0.94 . ?
C4 C5 1.371(4) . ?
C4 H4 0.94 . ?
C5 C6 1.392(4) . ?
C5 H5 0.94 . ?
C7 C8 1.366(4) . ?
C7 C11 1.496(4) . ?
C8 C9 1.501(4) . ?
C9 C9A 1.512(4) . ?
C9 C10 1.533(4) . ?
C9 H9 0.99 . ?
C9A C9B 1.377(4) . ?
C9A C9F 1.386(4) . ?
C9B C9C 1.386(5) . ?
C9B H9B 0.94 . ?
C9C C9D 1.358(5) . ?
C9C H9C 0.94 . ?
C9D C9E 1.379(6) . ?
C9D H9D 0.94 . ?
C9E C9F 1.385(5) . ?
C9E H9E 0.94 . ?
C9F H9F 0.94 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C11 C11A 1.527(4) . ?
C11 H11 0.99 . ?
C11A C11F 1.383(4) . ?
C11A C11B 1.385(4) . ?
C11B C11C 1.386(4) . ?
C11B H11B 0.94 . ?
C11C C11D 1.368(5) . ?
C11C H11C 0.94 . ?
C11D C11E 1.371(5) . ?
C11D H11D 0.94 . ?
C11E C11F 1.382(5) . ?
C11E H11E 0.94 . ?
C11F H11F 0.94 . ?
C12 C13 1.503(5) . ?
C13 C18 1.377(5) . ?
C13 C14 1.384(4) . ?
C14 C15 1.385(4) . ?
C14 H14 0.94 . ?
C15 C16 1.382(4) . ?
C15 H15 0.94 . ?
C16 C17 1.377(4) . ?
C17 C18 1.384(4) . ?
C17 H17 0.94 . ?
C18 H18 0.94 . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C20 H20C 0.97 . ?
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 C7 107.7(2) . . ?
C6 N1 C20 124.5(2) . . ?
C7 N1 C20 127.6(3) . . ?
C12 N2 C10 126.2(2) . . ?
C12 N2 C11 119.4(2) . . ?
C10 N2 C11 114.4(2) . . ?
C2 C1 C6 118.0(3) . . ?
C2 C1 C8 135.5(2) . . ?
C6 C1 C8 106.5(2) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.0(3) . . ?
C4 C5 H5 121 . . ?
C6 C5 H5 121 . . ?
N1 C6 C5 129.1(2) . . ?
N1 C6 C1 108.7(2) . . ?
C5 C6 C1 122.3(3) . . ?
C8 C7 N1 110.3(3) . . ?
C8 C7 C11 125.7(2) . . ?
N1 C7 C11 123.9(2) . . ?
C7 C8 C1 106.8(2) . . ?
C7 C8 C9 123.0(3) . . ?
C1 C8 C9 130.2(2) . . ?
C8 C9 C9A 113.7(2) . . ?
C8 C9 C10 108.6(2) . . ?
C9A C9 C10 113.7(2) . . ?
C8 C9 H9 106.8 . . ?
C9A C9 H9 106.8 . . ?
C10 C9 H9 106.8 . . ?
C9B C9A C9F 117.7(3) . . ?
C9B C9A C9 122.4(2) . . ?
C9F C9A C9 120.0(3) . . ?
C9A C9B C9C 121.8(3) . . ?
C9A C9B H9B 119.1 . . ?
C9C C9B H9B 119.1 . . ?
C9D C9C C9B 120.0(4) . . ?
C9D C9C H9C 120 . . ?
C9B C9C H9C 120 . . ?
C9C C9D C9E 119.5(4) . . ?
C9C C9D H9D 120.3 . . ?
C9E C9D H9D 120.3 . . ?
C9D C9E C9F 120.5(3) . . ?
C9D C9E H9E 119.7 . . ?
C9F C9E H9E 119.7 . . ?
C9E C9F C9A 120.6(4) . . ?
C9E C9F H9F 119.7 . . ?
C9A C9F H9F 119.7 . . ?
N2 C10 C9 112.2(2) . . ?
N2 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C7 107.2(2) . . ?
N2 C11 C11A 110.9(2) . . ?
C7 C11 C11A 116.0(2) . . ?
N2 C11 H11 107.5 . . ?
C7 C11 H11 107.5 . . ?
C11A C11 H11 107.5 . . ?
C11F C11A C11B 119.3(3) . . ?
C11F C11A C11 118.4(3) . . ?
C11B C11A C11 122.3(3) . . ?
C11A C11B C11C 119.6(3) . . ?
C11A C11B H11B 120.2 . . ?
C11C C11B H11B 120.2 . . ?
C11D C11C C11B 120.9(4) . . ?
C11D C11C H11C 119.5 . . ?
C11B C11C H11C 119.5 . . ?
C11C C11D C11E 119.5(3) . . ?
C11C C11D H11D 120.2 . . ?
C11E C11D H11D 120.2 . . ?
C11D C11E C11F 120.5(3) . . ?
C11D C11E H11E 119.8 . . ?
C11F C11E H11E 119.8 . . ?
C11E C11F C11A 120.2(3) . . ?
C11E C11F H11F 119.9 . . ?
C11A C11F H11F 119.9 . . ?
O1 C12 N2 121.8(3) . . ?
O1 C12 C13 120.3(3) . . ?
N2 C12 C13 117.8(3) . . ?
C18 C13 C14 119.6(3) . . ?
C18 C13 C12 120.7(3) . . ?
C14 C13 C12 119.7(3) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 Cl1 119.6(3) . . ?
C15 C16 Cl1 119.2(3) . . ?
C16 C17 C18 118.5(3) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C13 C18 C17 121.3(3) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.1(4) . . . . ?
C8 C1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C7 N1 C6 C5 -179.2(3) . . . . ?
C20 N1 C6 C5 -3.5(5) . . . . ?
C7 N1 C6 C1 0.2(3) . . . . ?
C20 N1 C6 C1 175.9(3) . . . . ?
C4 C5 C6 N1 -179.7(3) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C2 C1 C6 N1 178.9(2) . . . . ?
C8 C1 C6 N1 -1.5(3) . . . . ?
C2 C1 C6 C5 -1.6(4) . . . . ?
C8 C1 C6 C5 177.9(3) . . . . ?
C6 N1 C7 C8 1.3(3) . . . . ?
C20 N1 C7 C8 -174.3(3) . . . . ?
C6 N1 C7 C11 -174.5(3) . . . . ?
C20 N1 C7 C11 9.9(4) . . . . ?
N1 C7 C8 C1 -2.2(3) . . . . ?
C11 C7 C8 C1 173.5(3) . . . . ?
N1 C7 C8 C9 177.0(2) . . . . ?
C11 C7 C8 C9 -7.3(4) . . . . ?
C2 C1 C8 C7 -178.3(3) . . . . ?
C6 C1 C8 C7 2.3(3) . . . . ?
C2 C1 C8 C9 2.5(5) . . . . ?
C6 C1 C8 C9 -176.9(3) . . . . ?
C7 C8 C9 C9A 119.3(3) . . . . ?
C1 C8 C9 C9A -61.7(4) . . . . ?
C7 C8 C9 C10 -8.3(4) . . . . ?
C1 C8 C9 C10 170.7(3) . . . . ?
C8 C9 C9A C9B -32.2(4) . . . . ?
C10 C9 C9A C9B 92.7(3) . . . . ?
C8 C9 C9A C9F 147.0(3) . . . . ?
C10 C9 C9A C9F -88.1(3) . . . . ?
C9F C9A C9B C9C -0.1(4) . . . . ?
C9 C9A C9B C9C 179.1(3) . . . . ?
C9A C9B C9C C9D -0.5(5) . . . . ?
C9B C9C C9D C9E 1.0(6) . . . . ?
C9C C9D C9E C9F -0.8(6) . . . . ?
C9D C9E C9F C9A 0.1(6) . . . . ?
C9B C9A C9F C9E 0.4(5) . . . . ?
C9 C9A C9F C9E -178.9(3) . . . . ?
C12 N2 C10 C9 110.8(3) . . . . ?
C11 N2 C10 C9 -65.8(3) . . . . ?
C8 C9 C10 N2 42.1(3) . . . . ?
C9A C9 C10 N2 -85.5(3) . . . . ?
C12 N2 C11 C7 -130.5(3) . . . . ?
C10 N2 C11 C7 46.3(3) . . . . ?
C12 N2 C11 C11A 101.9(3) . . . . ?
C10 N2 C11 C11A -81.2(3) . . . . ?
C8 C7 C11 N2 -11.0(4) . . . . ?
N1 C7 C11 N2 164.1(2) . . . . ?
C8 C7 C11 C11A 113.5(3) . . . . ?
N1 C7 C11 C11A -71.4(3) . . . . ?
N2 C11 C11A C11F -66.0(3) . . . . ?
C7 C11 C11A C11F 171.4(2) . . . . ?
N2 C11 C11A C11B 115.5(3) . . . . ?
C7 C11 C11A C11B -7.1(4) . . . . ?
C11F C11A C11B C11C -0.5(4) . . . . ?
C11 C11A C11B C11C 178.1(3) . . . . ?
C11A C11B C11C C11D 0.1(5) . . . . ?
C11B C11C C11D C11E 0.2(5) . . . . ?
C11C C11D C11E C11F -0.1(5) . . . . ?
C11D C11E C11F C11A -0.3(5) . . . . ?
C11B C11A C11F C11E 0.6(4) . . . . ?
C11 C11A C11F C11E -178.0(3) . . . . ?
C10 N2 C12 O1 -176.1(3) . . . . ?
C11 N2 C12 O1 0.3(5) . . . . ?
C10 N2 C12 C13 6.1(4) . . . . ?
C11 N2 C12 C13 -177.5(3) . . . . ?
O1 C12 C13 C18 -98.8(4) . . . . ?
N2 C12 C13 C18 79.1(4) . . . . ?
O1 C12 C13 C14 78.7(4) . . . . ?
N2 C12 C13 C14 -103.5(3) . . . . ?
C18 C13 C14 C15 -1.2(4) . . . . ?
C12 C13 C14 C15 -178.7(3) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C14 C15 C16 Cl1 -178.8(2) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
Cl1 C16 C17 C18 178.3(2) . . . . ?
C14 C13 C18 C17 0.7(5) . . . . ?
C12 C13 C18 C17 178.2(3) . . . . ?
C16 C17 C18 C13 0.2(4) . . . . ?
#==============================================================================
data_wei-4b
_database_code_depnum_ccdc_archive 'CCDC 270611'
#===================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
(R,R) N-(1-tert-Butyl-3,3-dimethyl-2-trifluoromethanesulfonylamino-butyl)-
C,C,C-trifluoro-methanesulfonamide
;
_chemical_name_common ?
_chemical_formula_sum 'C12 H22 F6 N2 O4 S2'
_chemical_formula_moiety 'C12 H22 F6 N2 O4 S2'
_chemical_formula_weight 436.46
_chemical_melting_point ?
_chemical_compound_source ?
#===================================
# 6. CRYSTAL DATA
_symmetry_cell_setting tetragonal
_symmetry_space_group_name_H-M 'P 41 2 2'
_symmetry_space_group_name_Hall 'P 4w 2c'
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,-y,1/2+z
-y,+x,1/4+z
+y,-x,3/4+z
-x,+y,-z
+x,-y,1/2-z
+y,+x,3/4-z
-y,-x,1/4-z
_cell_length_a 12.2564(3)
_cell_length_b 12.2564(3)
_cell_length_c 13.4713(6)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2023.65(11)
_cell_formula_units_Z 4
_cell_measurement_temperature 100
_cell_measurement_reflns_used 7356
_cell_measurement_theta_min 2.79
_cell_measurement_theta_max 34.65
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.45
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_diffrn 1.433
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 904
_exptl_absorpt_coefficient_mu 0.335
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details none
#===================================
# 7. EXPERIMENTAL DATA
_diffrn_ambient_temperature 100
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source 'x-ray tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'Siemens SMART CCD diffractometer'
_diffrn_measurement_method 'scans with narrow frames '
_diffrn_standards_decay_% 0
_diffrn_reflns_number 61260
_diffrn_reflns_av_R_equivalents 0.064
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_theta_min 2.79
_diffrn_reflns_theta_max 34.65
_diffrn_reflns_reduction_process 61260
_reflns_number_total 4269
_diffrn_measured_fraction_theta_max 0.93
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_theta_full 30.51
_reflns_number_gt 3636
_reflns_threshold_expression I>3\s(I)
_computing_data_collection 'SMART (Siemens, 1995)'
_computing_cell_refinement 'SAINT (Siemens, 1995)'
_computing_data_reduction 'SAINT (Siemens, 1995)'
_computing_structure_solution
;
SIR97 (Altomare et al., 1997 ), KRYSTAL
;
_computing_structure_refinement 'modified ORFLS(1962), KRYSTAL'
_computing_molecular_graphics
;
ORTEP-III (Burnett & Johnson, 1996), KRYSTAL
;
_computing_publication_material KRYSTAL
_atom_type_scat_source IntTabIV
#===================================
# 8. REFINEMENT DATA
_refine_special_details
; The hydrogen atom on Nitrogen was located from a difference map but
not refined. The fluorine atoms have large displacement parameters
and the large peaks and holes in the final difference map are in this
region, hinting at some degree of disorder here.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w = 1/{[s~cs~(F^2^)+0.05F^2^]}^2^
;
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method
;
Type 1 Lorentzian isotropic (Becker and Coppens, 1974)
;
_refine_ls_extinction_coef 85(23)
_refine_ls_abs_structure_details
; The least squares refinement included a factor according to Rogers (1981).
3636 significant reflections were used, including 1466 Bijvoet pairs.
;
_refine_ls_abs_structure_Rogers 0.89(13)
_refine_ls_number_reflns 3636
_refine_ls_number_parameters 120
_refine_ls_number_restraints 0
_refine_ls_number_constraints 0
_refine_ls_R_factor_gt 0.044
_refine_ls_wR_factor_ref 0.093
_refine_ls_goodness_of_fit_ref 0.904
_refine_ls_shift/su_max 0.0046
_refine_ls_shift/su_mean 0.0005
_refine_diff_density_max 1.24(11)
_refine_diff_density_min -0.76(11)
#==========================================
# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
S1 0.44253(3) 0.20938(3) 0.30154(3) 0.0167(2) Uij
F1 0.53820(20) 0.38803(15) 0.35467(18) 0.0923(16) Uij
F2 0.64761(11) 0.26942(15) 0.30581(17) 0.0748(12) Uij
F3 0.54954(14) 0.35317(17) 0.20196(13) 0.0784(12) Uij
O1 0.34747(10) 0.27013(11) 0.27468(9) 0.0259(6) Uij
O2 0.47792(12) 0.11871(11) 0.24412(9) 0.0290(7) Uij
N1 0.44164(11) 0.17909(10) 0.41710(9) 0.0167(5) Uij
C1 0.5520(2) 0.3105(2) 0.2901(1) 0.0307(9) Uij
C2 0.4566(1) 0.0672(1) 0.4574(1) 0.0163(6) Uij
C3 0.3442(1) 0.0155(1) 0.4861(1) 0.0209(7) Uij
C4 0.2913(2) 0.0733(1) 0.5744(1) 0.0272(8) Uij
C5 0.3616(2) -0.1054(1) 0.5127(1) 0.0293(9) Uij
C6 0.2677(2) 0.0197(2) 0.3963(1) 0.0298(9) Uij
H1n 0.4096 0.2209 0.4530 0.0200 Uiso
H2 0.4857 0.0241 0.4051 0.0196 Uiso
H4a 0.2231 0.0418 0.5918 0.0326 Uiso
H4b 0.2802 0.1477 0.5577 0.0326 Uiso
H4c 0.3389 0.0685 0.6298 0.0326 Uiso
H5a 0.2934 -0.1368 0.5301 0.0352 Uiso
H5b 0.4104 -0.1109 0.5672 0.0352 Uiso
H5c 0.3912 -0.1429 0.4571 0.0352 Uiso
H6a 0.1994 -0.0117 0.4137 0.0358 Uiso
H6b 0.2989 -0.0200 0.3428 1.5306 Uiso
H6c 0.2571 0.0935 0.3767 1.5306 Uiso
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0198(2) 0.0190(2) 0.0112(1) -0.0001(1) 0.0005(1) 0.0008(1)
F1 0.1122(18) 0.0520(10) 0.1127(18) -0.0520(12) 0.0245(16) -0.0300(11)
F2 0.0236(6) 0.0702(11) 0.1306(17) -0.0098(6) -0.0091(8) 0.0616(12)
F3 0.0542(9) 0.1150(15) 0.0659(10) -0.0412(10) -0.0235(8) 0.0743(11)
O1 0.0222(5) 0.0385(7) 0.0172(6) 0.0044(5) -0.0011(4) 0.0069(5)
O2 0.0479(8) 0.0255(6) 0.0135(6) 0.0045(6) 0.0065(5) -0.0037(4)
N1 0.0245(6) 0.0149(5) 0.0107(5) 0.0021(5) 0.0024(5) 0.0006(4)
C1 0.0284(8) 0.0312(9) 0.0326(9) -0.0066(7) -0.0055(7) 0.0165(7)
C2 0.0224(6) 0.0128(5) 0.0137(6) -0.0006(5) 0.0011(5) 0.0001(5)
C3 0.0251(7) 0.0200(7) 0.0175(7) -0.0062(5) 0.0013(6) 0.0007(5)
C4 0.0280(8) 0.0301(8) 0.0234(8) -0.0059(7) 0.0077(6) -0.0003(6)
C5 0.0417(10) 0.0193(7) 0.0269(9) -0.0107(7) 0.0002(7) 0.0025(6)
C6 0.0268(9) 0.0350(9) 0.0277(9) -0.0091(7) -0.0023(7) 0.0021(7)
#=================================
# 10. MOLECULAR GEOMETRY
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 O2 1.422(1) . .
S1 O1 1.429(1) . .
S1 N1 1.600(1) . .
S1 C1 1.833(2) . .
F1 C1 1.299(3) . .
F2 C1 1.293(2) . .
F3 C1 1.298(2) . .
N1 C2 1.486(2) . .
C2 C2 1.564(3) . 5_656
C2 C3 1.565(2) . .
C3 C4 1.529(2) . .
C3 C6 1.533(2) . .
C3 C5 1.538(2) . .
N1 H1n 0.81 . .
C2 H2 0.95 . .
C4 H4b 0.95 . .
C4 H4c 0.95 . .
C4 H4a 0.95 . .
C5 H5b 0.95 . .
C5 H5a 0.95 . .
C5 H5c 0.95 . .
C6 H6b 0.95 . .
C6 H6a 0.95 . .
C6 H6c 0.95 . .
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_2
_geom_angle_site_symmetry_3
O1 S1 O2 121.21(9) . . .
N1 S1 O2 110.49(7) . . .
C1 S1 O2 105.04(9) . . .
N1 S1 O1 111.19(7) . . .
C1 S1 O1 102.89(8) . . .
C1 S1 N1 104.10(8) . . .
S1 N1 C2 124.6(1) . . .
F3 C1 F2 109.1(2) . . .
F1 C1 F2 107.0(2) . . .
S1 C1 F2 112.7(1) . . .
F1 C1 F3 108.3(2) . . .
S1 C1 F3 109.4(1) . . .
S1 C1 F1 110.1(2) . . .
C2 C2 N1 110.61(8) 5_656 . .
C3 C2 N1 110.8(1) . . .
C3 C2 C2 114.6(1) . . 5_656
C6 C3 C4 109.8(2) . . .
C5 C3 C4 108.9(1) . . .
C2 C3 C4 112.2(1) . . .
C5 C3 C6 107.5(1) . . .
C2 C3 C6 109.3(1) . . .
C2 C3 C5 109.1(1) . . .
C2 N1 H1n 115.3 . . .
S1 N1 H1n 116.1 . . .
N1 C2 H2 106.8 . . .
C2 C2 H2 106.8 5_656 . .
C3 C2 H2 106.8 . . .
H4c C4 H4b 109.5 . . .
H4a C4 H4b 108.8 . . .
C3 C4 H4b 108.8 . . .
H4a C4 H4c 108.8 . . .
C3 C4 H4c 108.8 . . .
C3 C4 H4a 112.2 . . .
H5a C5 H5b 109.6 . . .
H5c C5 H5b 109.5 . . .
C3 C5 H5b 109.6 . . .
H5c C5 H5a 109.6 . . .
C3 C5 H5a 109.1 . . .
C3 C5 H5c 109.6 . . .
H6a C6 H6b 109.5 . . .
H6c C6 H6b 109.5 . . .
C3 C6 H6b 109.6 . . .
H6c C6 H6a 109.5 . . .
C3 C6 H6a 109.3 . . .
C3 C6 H6c 109.5 . . .
loop_
_publ_manuscript_incl_extra_item
'_geom_bond_atom_site_label_D'
'_geom_bond_atom_site_label_H'
'_geom_contact_atom_site_label_A'
'_geom_bond_distance_DH'
'_geom_contact_distance_HA'
'_geom_contact_distance_DA'
'_geom_angle_DHA'
'_geom_contact_site_symmetry_A'
loop_
_geom_bond_atom_site_label_D
_geom_bond_atom_site_label_H
_geom_contact_atom_site_label_A
_geom_bond_distance_DH
_geom_contact_distance_HA
_geom_contact_distance_DA
_geom_angle_DHA
_geom_contact_site_symmetry_A
N1 H1n O1 0.807 2.328 3.048(2) 149.1(1) 7_555
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C2 C2 N1 19.4(2) . . 5_656 5_656
S1 N1 C2 C2 131.4(1) . . . 5_656
# Dihedral angle:
# S1 N1 C2 - S1 N1 C2 162.8(2) . . . 5_656
# Intramolecular distances:
# N1 N1 2.652(3) . 5_656
# H1n H1n 2.552(0) . 5_656
# N1 H1n 2.578(1) . 5_656
# H1n H2 3.333(0) . 5_656
# H2 H2 2.581(0) . 5_656
# S1 S1 5.530(1) . 5_656
data_wei-4c
_database_code_depnum_ccdc_archive 'CCDC 270612'
#===================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
(R,R) N-(1,2-Dicyclohexyl-2-trifluoromethanesulfonylamino-ethyl9-
C,C,C-trifluoro-methanesulfonamide
;
_chemical_formula_sum 'C16 H26 F6 N2 O4 S2'
_chemical_formula_moiety 'C16 H26 F6 N2 O4 S2'
_chemical_formula_weight 488.53
#===================================
# 6. CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,+y,1/2-z
-x,-y,-z
+x,-y,1/2+z
1/2+x,1/2+y,+z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+z
_cell_length_a 20.6214(6)
_cell_length_b 10.7987(7)
_cell_length_c 9.401(3)
_cell_angle_alpha 90.000
_cell_angle_beta 95.972(3)
_cell_angle_gamma 90.000
_cell_volume 2082.1(7)
_cell_formula_units_Z 4
_cell_measurement_temperature 100
_cell_measurement_reflns_used 8505
_cell_measurement_theta_min 2.97
_cell_measurement_theta_max 33.94
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.56
_exptl_crystal_size_mid 0.42
_exptl_crystal_size_min 0.02
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_diffrn 1.559
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1016
_exptl_absorpt_coefficient_mu 0.335
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS, 1996 '
_exptl_absorpt_correction_T_min 0.773
_exptl_absorpt_correction_T_max 1.000
#===================================
# 7. EXPERIMENTAL DATA
_diffrn_ambient_temperature 100
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source 'x-ray tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'Siemens SMART CCD diffractometer'
_diffrn_measurement_method 'scans with narrow frames'
_diffrn_standards_decay_% 0
_diffrn_reflns_number 33027
_diffrn_reflns_av_R_equivalents 0.109
_diffrn_reflns_limit_h_min -32
_diffrn_reflns_limit_h_max 32
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 2.97
_diffrn_reflns_theta_max 33.94
_diffrn_reflns_reduction_process 33027
_reflns_number_total 4126
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_theta_full 33.94
_reflns_number_gt 2968
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART (Siemens, 1995)'
_computing_cell_refinement 'SAINT (Siemens, 1995)'
_computing_data_reduction 'SAINT (Siemens, 1995)'
_computing_structure_solution
;
SIR97 (Altomare et al., 1997 ), KRYSTAL
;
_computing_structure_refinement 'modified ORFLS(1962), KRYSTAL'
_computing_molecular_graphics
;
ORTEP-III (Burnett & Johnson, 1996), KRYSTAL
;
_computing_publication_material KRYSTAL
_atom_type_scat_source IntTabIV
#===================================
# 8. REFINEMENT DATA
_refine_special_details
; The structure consists of layers in the bc-plane with very little interaction
between layers resulting in serious disorder in the stacking of planes. Many
lines in reciporcal space parallel to the a-axis are continuous lines with few
spots and gaps. Datasets from several crystals have been collected showing
varying degrees of twinning. Structure solution in various space groups all
agree on the same structure for one layer. The present solution neglects some
streaks with weak maxima but accounts reasonably for most of the data; the
agreement was improved by giving separate scalefactors to reflections on lines
with continuous streaks and to h0l, which is common to two twins.
The final difference map shows maxima and minima in the region of the cyclo-
hexane rings, but it was not possible to fit them to a model for an alternative
orientation of the ring, and it is consireded most likely an effect of neglect
of twin-contributions to many reflections.
Another crystal had its strong reflections indexed on a triclinic cell with
a = 9.432(2), b = 10.891(3), c = 11.339(3), \a = 104.54, \b = 109.09(2),
\c = 90.05(2). The disorder-streaks had less well defined maxima.
It solved in space group P -1 to give the same structure within the layer but a
different stacking of layers. The refinement was less satisfactory, possibly
because the influence of twinning and other stackings disorders were neglected.
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^
where A = 0.10 and B = 5.0
;
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_number_reflns 2968
_refine_ls_number_parameters 141
_refine_ls_number_restraints 0
_refine_ls_number_constraints 2
_refine_ls_R_factor_gt 0.143
_refine_ls_wR_factor_ref 0.169
_refine_ls_goodness_of_fit_ref 1.166
_refine_ls_shift/su_max 0.0006
_refine_ls_shift/su_mean 0.0001
_refine_diff_density_max 2.9(1)
_refine_diff_density_min -1.3(1)
#==========================================
# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
S 0.06927(7) 0.3352(1) 0.4832(1) 0.0155(6) Uij
F1 0.1777(2) 0.2910(5) 0.6464(5) 0.042(3) Uij
F2 0.1498(3) 0.4798(5) 0.6387(5) 0.048(3) Uij
F3 0.1888(2) 0.3946(5) 0.4581(4) 0.038(2) Uij
O1 0.0764(2) 0.2118(4) 0.4303(5) 0.023(2) Uij
O2 0.0515(2) 0.4365(4) 0.3890(5) 0.025(2) Uij
N 0.0253(2) 0.3357(4) 0.6131(5) 0.016(2) Uij
C1 -0.0056(2) 0.2238(5) 0.6677(5) 0.013(2) Uij
C2 -0.0776(3) 0.2145(5) 0.6081(6) 0.016(2) Uij
C3 -0.1101(3) 0.1006(6) 0.6624(6) 0.020(3) Uij
C4 -0.1817(3) 0.0883(7) 0.6018(6) 0.026(3) Uij
C5 -0.1900(3) 0.0925(7) 0.4380(7) 0.028(3) Uij
C6 -0.1573(3) 0.2066(7) 0.3839(6) 0.027(3) Uij
C7 -0.0862(3) 0.2153(6) 0.4433(6) 0.022(3) Uij
C8 0.1511(3) 0.3793(6) 0.5627(6) 0.023(3) Uij
H1n 0.0032 0.4002 0.6122 0.019 Uiso
H1 0.0162 0.1537 0.6346 0.016 Uiso
H2 -0.0995 0.2851 0.6400 0.019 Uiso
H3a -0.1079 0.1053 0.7637 0.024 Uiso
H3b -0.0871 0.0294 0.6359 0.024 Uiso
H4a -0.2058 0.1544 0.6374 0.032 Uiso
H4b -0.1981 0.0116 0.6323 0.032 Uiso
H5a -0.2352 0.0945 0.4054 0.034 Uiso
H5b -0.1709 0.0206 0.4018 0.034 Uiso
H6a -0.1796 0.2782 0.4121 0.032 Uiso
H6b -0.1599 0.2031 0.2825 0.032 Uiso
H7a -0.0634 0.1467 0.4095 0.027 Uiso
H7b -0.0685 0.2900 0.4105 0.027 Uiso
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S 0.0171(6) 0.0161(7) 0.0137(5) -0.0001(5) 0.0040(4) 0.0025(5)
F1 0.030(2) 0.053(3) 0.040(2) 0.000(2) -0.005(2) 0.023(2)
F2 0.056(3) 0.047(3) 0.041(3) -0.031(2) 0.005(2) -0.014(2)
F3 0.017(2) 0.069(3) 0.029(2) -0.009(2) 0.008(1) 0.010(2)
O1 0.030(2) 0.024(2) 0.018(2) 0.002(2) 0.011(2) -0.004(2)
O2 0.033(2) 0.021(2) 0.022(2) 0.006(2) 0.007(2) 0.009(2)
N 0.019(2) 0.012(2) 0.016(2) 0.000(2) 0.004(1) 0.003(2)
C1 0.016(2) 0.012(2) 0.012(2) -0.001(2) 0.001(2) -0.002(2)
C2 0.025(3) 0.011(2) 0.012(2) -0.003(2) 0.001(2) 0.001(2)
C3 0.017(2) 0.024(3) 0.018(2) -0.007(2) -0.002(2) 0.007(2)
C4 0.020(3) 0.042(4) 0.016(2) -0.013(3) -0.003(2) 0.003(2)
C5 0.015(3) 0.042(4) 0.026(3) -0.006(2) -0.003(2) -0.003(3)
C6 0.020(3) 0.043(4) 0.016(2) -0.004(3) -0.005(2) 0.000(3)
C7 0.019(2) 0.036(3) 0.012(2) -0.005(2) 0.000(2) 0.002(2)
C8 0.014(2) 0.033(3) 0.022(3) -0.005(2) 0.001(2) 0.012(2)
#=================================
# 10. MOLECULAR GEOMETRY
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S O2 1.432(4) . .
S O1 1.434(5) . .
S N 1.595(4) . .
S C8 1.838(6) . .
F1 C8 1.319(7) . .
F2 C8 1.301(8) . .
F3 C8 1.325(7) . .
N C1 1.481(7) . .
C1 C2 1.536(8) . .
C1 C1 1.541(10) . 2_556
C2 C7 1.541(7) . .
C2 C3 1.513(8) . .
C3 C4 1.534(8) . .
C4 C5 1.533(9) . .
C5 C6 1.517(10) . .
C6 C7 1.518(8) . .
N H1n 0.83 . .
C1 H1 0.95 . .
C2 H2 0.95 . .
C3 H3b 0.95 . .
C3 H3a 0.95 . .
C4 H4a 0.95 . .
C4 H4b 0.95 . .
C5 H5b 0.95 . .
C5 H5a 0.95 . .
C6 H6b 0.95 . .
C6 H6a 0.95 . .
C7 H7a 0.95 . .
C7 H7b 0.95 . .
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_2
_geom_angle_site_symmetry_3
O1 S O2 121.6(3) . . .
N S O2 110.0(3) . . .
C8 S O2 102.7(3) . . .
N S O1 110.8(3) . . .
C8 S O1 105.0(3) . . .
C8 S N 105.0(3) . . .
S N C1 124.1(4) . . .
C2 C1 N 111.2(4) . . .
C1 C1 N 108.8(3) 2_556 . .
C1 C1 C2 114.0(5) 2_556 . .
C1 C2 C7 112.0(5) . . .
C3 C2 C7 109.5(5) . . .
C3 C2 C1 112.0(4) . . .
C2 C3 C4 112.8(5) . . .
C5 C4 C3 112.0(5) . . .
C6 C5 C4 110.6(5) . . .
C7 C6 C5 111.9(5) . . .
C6 C7 C2 112.1(5) . . .
F3 C8 F1 107.1(5) . . .
F2 C8 F1 107.8(5) . . .
S C8 F1 111.3(4) . . .
F2 C8 F3 110.5(5) . . .
S C8 F3 108.4(4) . . .
S C8 F2 111.7(5) . . .
C1 N H1n 115.6 . . .
S N H1n 110.4 . . .
N C1 H1 107.6 . . .
C2 C1 H1 107.5 . . .
C1 C1 H1 107.5 2_556 . .
C7 C2 H2 107.7 . . .
C1 C2 H2 107.7 . . .
C3 C2 H2 107.7 . . .
H3a C3 H3b 109.4 . . .
C4 C3 H3b 108.6 . . .
C2 C3 H3b 108.6 . . .
C4 C3 H3a 108.7 . . .
C2 C3 H3a 108.6 . . .
H4b C4 H4a 109.5 . . .
C3 C4 H4a 108.9 . . .
C5 C4 H4a 108.8 . . .
C3 C4 H4b 108.8 . . .
C5 C4 H4b 108.8 . . .
H5a C5 H5b 109.5 . . .
C4 C5 H5b 109.1 . . .
C6 C5 H5b 109.2 . . .
C4 C5 H5a 109.3 . . .
C6 C5 H5a 109.2 . . .
H6a C6 H6b 109.4 . . .
C5 C6 H6b 108.8 . . .
C7 C6 H6b 108.9 . . .
C5 C6 H6a 108.9 . . .
C7 C6 H6a 108.9 . . .
H7b C7 H7a 109.5 . . .
C2 C7 H7a 108.8 . . .
C6 C7 H7a 108.8 . . .
C2 C7 H7b 108.8 . . .
C6 C7 H7b 108.8 . . .
loop_
_publ_manuscript_incl_extra_item
'_geom_bond_atom_site_label_D'
'_geom_bond_atom_site_label_H'
'_geom_contact_atom_site_label_A'
'_geom_bond_distance_DH'
'_geom_contact_distance_HA'
'_geom_contact_distance_DA'
'_geom_angle_DHA'
'_geom_contact_site_symmetry_A'
loop_
_geom_bond_atom_site_label_D
_geom_bond_atom_site_label_H
_geom_contact_atom_site_label_A
_geom_bond_distance_DH
_geom_contact_distance_HA
_geom_contact_distance_DA
_geom_angle_DHA
_geom_contact_site_symmetry_A
N H1n O1 0.832(5) 2.092(4) 2.924(7) 118.1(3) 3_567
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N C1 C1 N 61.2(7) . . 2_556 2_556
S N C1 C1 134.5(4) . . . 2_556
C2 C1 C1 C2 171.8(6) . . 2_556 2_556
S C1 C1 S 112.7(5) . . 2_556 2_556
data_wei-4d
_database_code_depnum_ccdc_archive 'CCDC 270613'
#===================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
(S,S) C,C,C-Trifluoro-N-(2-trifluoromethanesulfonylamino-cyclohexyl)
-methanesulfonamide
;
_chemical_name_common ?
_chemical_formula_sum 'C9.80 H12 F6 N2 O4 S2'
_chemical_formula_moiety 'C8 H12 F6 N2 O4 S2, C1.80'
_chemical_formula_weight 397.43
_chemical_melting_point ?
_chemical_compound_source ?
#===================================
# 6. CRYSTAL DATA
_symmetry_cell_setting trigonal
_symmetry_space_group_name_H-M 'P 32 2 1'
_symmetry_space_group_name_Hall 'P 32 2'
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-y,+x-y,2/3+z
-x+y,-x,1/3+z
+y,+x,-z
+x-y,-y,1/3-z
-x,-x+y,2/3-z
_cell_length_a 14.3841(2)
_cell_length_b 14.3841(2)
_cell_length_c 13.9800(4)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 120
_cell_volume 2504.97(9)
_cell_formula_units_Z 6
_cell_measurement_temperature 100
_cell_measurement_reflns_used 5844
_cell_measurement_theta_min 2.83
_cell_measurement_theta_max 32.96
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.56
_exptl_crystal_size_mid 0.06
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_diffrn 1.581
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1209.2
_exptl_absorpt_coefficient_mu 0.398
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details none
#===================================
# 7. EXPERIMENTAL DATA
_diffrn_ambient_temperature 100
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source 'x-ray tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'Siemens SMART CCD diffractometer'
_diffrn_measurement_method '\w rotation scans with narrow frames'
_diffrn_standards_decay_% 0
_diffrn_reflns_number 24180
_diffrn_reflns_av_R_equivalents 0.081
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_k_min -22
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_theta_min 2.83
_diffrn_reflns_theta_max 32.96
_diffrn_reflns_reduction_process 24180
_reflns_number_total 6270
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measured_fraction_theta_full 1.00
_diffrn_reflns_theta_full 32.96
_reflns_number_gt 5312
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART (Siemens, 1995)'
_computing_cell_refinement 'SAINT (Siemens, 1995)'
_computing_data_reduction 'SAINT (Siemens, 1995)'
_computing_structure_solution
;
SIR97 (Altomare et al., 1997 ), KRYSTAL
;
_computing_structure_refinement 'modified ORFLS(1962), KRYSTAL'
_computing_molecular_graphics
;
ORTEP-III (Burnett & Johnson, 1996), KRYSTAL
;
_computing_publication_material KRYSTAL
_atom_type_scat_source IntTabIV
#===================================
# 8. REFINEMENT DATA
_refine_special_details
; The structure contains large channels along the unique axis filled by
solvent molecules (n-hexane). The solvent is completely disordered, and the
carbon atoms C11-C14 are included at the most important peak positions in
order to improve the model of the main residue. The peaks form an infinite
chain.
The hydrogen atoms on nitrogen were located from a difference fourier map
but were not refined. They are found to point towards oxygen atoms in
neighbouring molecules.
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^
where A = 0.03 and B = 0.0
;
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_abs_structure_details
; The least squares refinement included a factor according to Rogers (1981).
5312 significant reflections were used, including 2288 Bijvoet pairs.
;
_refine_ls_abs_structure_Rogers 0.79(9)
_refine_ls_number_reflns 5312
_refine_ls_number_parameters 215
_refine_ls_number_restraints 0
_refine_ls_number_constraints 3
_refine_ls_R_factor_gt 0.034
_refine_ls_wR_factor_ref 0.036
_refine_ls_goodness_of_fit_ref 1.027
_refine_ls_shift/su_max 0.0043
_refine_ls_shift/su_mean 0.0003
_refine_diff_density_max 0.88(8)
_refine_diff_density_min -0.60(8)
#==========================================
# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
S1 0.68404(4) 0.41124(3) 0.92124(2) 0.0220(3) Uij 1.0
S2 0.68015(3) 0.13666(4) 0.93408(3) 0.0225(3) Uij 1.0
F1 0.7398(2) 0.6126(1) 0.91148(13) 0.0800(16) Uij 1.0
F2 0.6446(1) 0.5179(1) 0.79345(8) 0.0456(11) Uij 1.0
F3 0.5698(2) 0.5051(1) 0.92854(10) 0.0641(16) Uij 1.0
F4 0.7397(1) -0.0063(1) 0.92304(10) 0.0514(13) Uij 1.0
F5 0.6917(2) 0.0139(1) 1.06451(9) 0.0579(14) Uij 1.0
F6 0.5721(1) -0.0707(1) 0.95551(9) 0.0503(11) Uij 1.0
O1 0.7703(1) 0.4266(1) 0.86050(8) 0.0292(9) Uij 1.0
O2 0.6960(1) 0.4197(1) 1.02280(7) 0.0324(9) Uij 1.0
O3 0.7868(1) 0.2151(1) 0.95780(11) 0.0397(11) Uij 1.0
O4 0.6423(1) 0.1185(1) 0.83778(7) 0.0293(9) Uij 1.0
N1 0.5779(1) 0.3050(1) 0.89403(8) 0.0247(9) Uij 1.0
N2 0.5974(1) 0.1474(1) 1.00138(9) 0.0245(10) Uij 1.0
C1 0.4927(1) 0.2350(1) 0.96202(10) 0.0215(10) Uij 1.0
C2 0.3837(2) 0.2167(2) 0.93030(12) 0.0275(12) Uij 1.0
C3 0.2968(2) 0.1437(2) 1.00150(14) 0.0311(13) Uij 1.0
C4 0.2958(2) 0.0379(2) 1.01540(13) 0.0298(12) Uij 1.0
C5 0.4055(2) 0.0565(1) 1.04462(12) 0.0253(11) Uij 1.0
C6 0.4914(1) 0.1287(1) 0.97259(10) 0.0201(10) Uij 1.0
C7 0.6580(2) 0.5186(2) 0.88710(15) 0.0404(16) Uij 1.0
C8 0.6697(2) 0.0105(2) 0.97142(13) 0.0356(16) Uij 1.0
H1n 0.5702 0.2946 0.8322 0.030 Uiso 1.0
H2n 0.6200 0.1600 1.0533 0.029 Uiso 1.0
H1 0.5090 0.2695 1.0226 0.026 Uiso 1.0
H2a 0.3671 0.1839 0.8690 0.033 Uiso 1.0
H2b 0.3860 0.2838 0.9271 0.033 Uiso 1.0
H3a 0.2287 0.1289 0.9781 0.037 Uiso 1.0
H3b 0.3102 0.1795 1.0614 0.037 Uiso 1.0
H4a 0.2752 -0.0013 0.9571 0.036 Uiso 1.0
H4b 0.2454 -0.0027 1.0639 0.036 Uiso 1.0
H5a 0.4033 -0.0105 1.0478 0.030 Uiso 1.0
H5b 0.4236 0.0899 1.1057 0.030 Uiso 1.0
H6 0.4739 0.0935 0.9123 0.024 Uiso 1.0
C11 0.940(2) 1.000 0.167 0.204(5) Uiso 0.42(1)
C12 0.896(2) 0.922(1) 0.106(1) 0.204 Uiso 0.59(2)
C13 0.953(2) 0.969(2) 0.036(2) 0.204 Uiso 0.50(1)
C14 1.011(3) 0.977(4) 0.154(3) 0.204 Uiso 0.29(1)
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0290(2) 0.0253(2) 0.0080(1) 0.0107(2) 0.0004(1) 0.0003(1)
S2 0.0232(2) 0.0287(2) 0.0154(1) 0.0130(2) 0.0010(1) 0.0003(1)
F1 0.1038(16) 0.0268(7) 0.0944(13) 0.0213(10) -0.0399(11) -0.0155(8)
F2 0.0659(10) 0.0482(8) 0.0300(6) 0.0340(8) 0.0004(6) 0.0137(5)
F3 0.0990(14) 0.0833(12) 0.0472(8) 0.0735(12) 0.0116(8) -0.0031(8)
F4 0.0679(10) 0.0683(10) 0.0456(7) 0.0548(9) -0.0089(7) -0.0132(7)
F5 0.1064(13) 0.0672(10) 0.0243(6) 0.0617(10) -0.0132(7) 0.0014(6)
F6 0.0646(10) 0.0285(6) 0.0467(7) 0.0149(7) 0.0061(7) 0.0007(5)
O1 0.0310(7) 0.0393(7) 0.0128(4) 0.0142(6) 0.0043(5) 0.0034(5)
O2 0.0353(7) 0.0409(8) 0.0078(4) 0.0091(6) -0.0016(4) -0.0018(5)
O3 0.0265(7) 0.0458(9) 0.0406(8) 0.0134(7) -0.0015(6) -0.0071(7)
O4 0.0361(7) 0.0458(8) 0.0110(4) 0.0243(6) 0.0039(4) 0.0017(4)
N1 0.0305(8) 0.0272(7) 0.0073(4) 0.0077(6) 0.0022(5) 0.0005(5)
N2 0.0263(8) 0.0379(9) 0.0118(5) 0.0180(7) -0.0024(5) -0.0052(5)
C1 0.0273(8) 0.0244(8) 0.0106(5) 0.0113(7) 0.0028(5) 0.0007(5)
C2 0.0324(10) 0.0311(9) 0.0238(7) 0.0193(8) -0.0011(7) 0.0005(7)
C3 0.0267(10) 0.0334(11) 0.0352(9) 0.0166(8) 0.0040(7) -0.0036(8)
C4 0.0262(9) 0.0292(10) 0.0310(9) 0.0116(8) 0.0080(7) 0.0003(7)
C5 0.0319(9) 0.0250(8) 0.0182(6) 0.0137(8) 0.0065(6) 0.0033(6)
C6 0.0229(8) 0.0266(8) 0.0113(5) 0.0128(7) 0.0009(5) -0.0007(5)
C7 0.0608(15) 0.0328(11) 0.0306(9) 0.0257(11) -0.0045(9) -0.0041(8)
C8 0.0545(13) 0.0407(12) 0.0221(8) 0.0318(11) -0.0064(8) -0.0026(8)
#=================================
# 10. MOLECULAR GEOMETRY
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 O1 1.427(1) . .
S1 O2 1.428(1) . .
S1 N1 1.574(2) . .
S1 C7 1.825(2) . .
S2 O3 1.416(2) . .
S2 O4 1.426(1) . .
S2 N2 1.585(1) . .
S2 C8 1.821(2) . .
F1 C7 1.319(3) . .
F2 C7 1.323(2) . .
F3 C7 1.318(3) . .
F4 C8 1.331(2) . .
F5 C8 1.334(2) . .
F6 C8 1.321(3) . .
N1 C1 1.479(2) . .
N2 C6 1.465(2) . .
C1 C2 1.520(2) . .
C1 C6 1.527(2) . .
C2 C3 1.531(3) . .
C3 C4 1.528(3) . .
C4 C5 1.519(3) . .
C5 C6 1.528(2) . .
N1 H1n 0.88 . .
N2 H2n 0.78 . .
C1 H1 0.95 . .
C2 H2a 0.95 . .
C2 H2b 0.95 . .
C3 H3b 0.95 . .
C3 H3a 0.95 . .
C4 H4a 0.95 . .
C4 H4b 0.95 . .
C5 H5a 0.95 . .
C5 H5b 0.95 . .
C6 H6 0.95 . .
C11 C14 1.229(30) . .
C11 C14 1.229(30) . 5_675
C11 C12 1.296(18) . .
C11 C12 1.296(18) . 5_675
C12 C13 1.233(19) . .
C12 C14 1.581(38) . .
C13 C13 1.074(41) . 4_555
C13 C14 1.831(47) . .
C14 C14 0.68(8) . 5_675
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_2
_geom_angle_site_symmetry_3
O2 S1 O1 121.32(8) . . .
N1 S1 O1 110.63(8) . . .
C7 S1 O1 104.1(1) . . .
N1 S1 O2 109.90(7) . . .
C7 S1 O2 104.78(9) . . .
C7 S1 N1 104.4(1) . . .
O4 S2 O3 121.95(9) . . .
N2 S2 O3 110.54(8) . . .
C8 S2 O3 104.1(1) . . .
N2 S2 O4 109.97(7) . . .
C8 S2 O4 104.74(9) . . .
C8 S2 N2 103.64(9) . . .
S1 N1 C1 125.3(1) . . .
S2 N2 C6 125.6(1) . . .
C2 C1 N1 111.3(1) . . .
C6 C1 N1 109.6(1) . . .
C6 C1 C2 111.1(1) . . .
C3 C2 C1 110.3(1) . . .
C2 C3 C4 111.4(2) . . .
C3 C4 C5 111.5(2) . . .
C6 C5 C4 111.0(1) . . .
C1 C6 N2 110.6(1) . . .
C5 C6 N2 110.9(1) . . .
C5 C6 C1 110.2(1) . . .
F1 C7 F3 109.6(2) . . .
F2 C7 F3 108.0(2) . . .
S1 C7 F3 110.5(2) . . .
F2 C7 F1 108.4(2) . . .
S1 C7 F1 110.2(2) . . .
S1 C7 F2 110.1(1) . . .
F4 C8 F6 108.7(2) . . .
F5 C8 F6 108.9(2) . . .
S2 C8 F6 110.7(1) . . .
F5 C8 F4 108.4(2) . . .
S2 C8 F4 110.0(2) . . .
S2 C8 F5 110.0(1) . . .
C1 N1 H1n 121.9 . . .
S1 N1 H1n 112.5 . . .
C6 N2 H2n 125.0 . . .
S2 N2 H2n 109.2 . . .
N1 C1 H1 108.3 . . .
C2 C1 H1 108.3 . . .
C6 C1 H1 108.2 . . .
H2b C2 H2a 109.5 . . .
C1 C2 H2a 109.3 . . .
C3 C2 H2a 109.3 . . .
C1 C2 H2b 109.2 . . .
C3 C2 H2b 109.2 . . .
H3a C3 H3b 109.4 . . .
C4 C3 H3b 109.0 . . .
C2 C3 H3b 109.0 . . .
C4 C3 H3a 109.0 . . .
C2 C3 H3a 109.0 . . .
H4b C4 H4a 109.4 . . .
C5 C4 H4a 108.9 . . .
C3 C4 H4a 109.0 . . .
C5 C4 H4b 108.9 . . .
C3 C4 H4b 109.0 . . .
H5b C5 H5a 109.5 . . .
C4 C5 H5a 109.2 . . .
C6 C5 H5a 109.0 . . .
C4 C5 H5b 109.2 . . .
C6 C5 H5b 109.0 . . .
N2 C6 H6 108.4 . . .
C1 C6 H6 108.4 . . .
C5 C6 H6 108.3 . . .
C12 C11 C14 109.0(25) 5_675 . .
C12 C11 C14 77.5(21) . . .
C12 C11 C12 173.6(27) 5_675 . .
C11 C12 C13 98.4(17) . . .
C14 C12 C13 80.2(24) . . .
C12 C13 C13 140.6(17) . . 4_555
C14 C13 C13 135.4(31) . . 4_555
C14 C13 C12 58.3(18) . . .
C11 C14 C14 74.0(19) . . 5_675
C12 C14 C14 126.3(23) . . 5_675
C13 C14 C14 121(8) . . 5_675
C13 C14 C11 74.6(20) . . .
loop_
_publ_manuscript_incl_extra_item
'_geom_bond_atom_site_label_D'
'_geom_bond_atom_site_label_H'
'_geom_contact_atom_site_label_A'
'_geom_bond_distance_DH'
'_geom_contact_distance_HA'
'_geom_contact_distance_DA'
'_geom_angle_DHA'
'_geom_contact_site_symmetry_A'
loop_
_geom_bond_atom_site_label_D
_geom_bond_atom_site_label_H
_geom_contact_atom_site_label_A
_geom_bond_distance_DH
_geom_contact_distance_HA
_geom_contact_distance_DA
_geom_angle_DHA
_geom_contact_site_symmetry_A
N1 H1n O2 0.88 2.03 2.892(2) 170 2_654
N2 H2n O1 0.78 2.15 2.890(2) 160 3_665
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C1 C6 N2 55.6(2) . . . .
S1 N1 C1 C6 -111.1(1) . . . .
C1 C6 N2 S2 -105.4(1) . . . .
#Dihedral angle:
# S1 N1 C1 - C1' N1' S2' 51.8(1) . . . .
# Intramolecular distances:
# S1 S2 3.926(1) . .
# N1 N2 2.844(2) . .
# N1 H2n 3.307(1) . .
# N2 H1n 3.324(1) . .
# H1n H2n 3.899(0) . .
# H1n H5b 2.745(0) . .
# H2n H1 2.780(0) . .
#==============================================================================
data_wei-4a
_database_code_depnum_ccdc_archive 'CCDC 272816'
#===================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
(R,R) N-(1,2-Diphenyl-2-trifluoromethanesulfonylamino-ethyl)-
C,C,C-trifluoro-methanesulfonamide
;
_chemical_formula_sum 'C16 H14 F6 N2 O4 S2'
_chemical_formula_moiety 'C16 H14 F6 N2 O4 S2'
_chemical_formula_weight 476.42
_chemical_melting_point ?
_chemical_compound_source ?
#===================================
# 6. CRYSTAL DATA
_symmetry_cell_setting hexagonal
_symmetry_space_group_name_H-M 'P 65 2 2'
_symmetry_space_group_name_Hall 'P 65 2 (0 0 1)'
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-y,+x-y,2/3+z
-x+y,-x,1/3+z
-x,-y,1/2+z
+y,-x+y,1/6+z
+x-y,+x,5/6+z
+y,+x,2/3-z
+x-y,-y,-z
-x,-x+y,1/3-z
-y,-x,1/6-z
-x+y,+y,1/2-z
+x,+x-y,5/6-z
_cell_length_a 11.6353(10)
_cell_length_b 11.6353(10)
_cell_length_c 52.806(9)
_cell_angle_alpha 90.000
_cell_angle_beta 90.000
_cell_angle_gamma 120.000
_cell_volume 6191.1(13)
_cell_formula_units_Z 12
_cell_measurement_temperature 100
_cell_measurement_reflns_used 7007
_cell_measurement_theta_min 3.07
_cell_measurement_theta_max 28.14
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.54
_exptl_crystal_size_mid 0.07
_exptl_crystal_size_min 0.06
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_diffrn 1.533
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2904
_exptl_absorpt_coefficient_mu 0.336
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details none
#===================================
# 7. EXPERIMENTAL DATA
_diffrn_ambient_temperature 100
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source 'x-ray tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'Siemens SMART CCD diffractometer'
_diffrn_measurement_method 'scans with narrow frames '
_diffrn_standards_decay_% 0
_diffrn_reflns_number 62518
_diffrn_reflns_av_R_equivalents 0.107
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -66
_diffrn_reflns_limit_l_max 55
_diffrn_reflns_theta_min 3.07
_diffrn_reflns_theta_max 28.14
_diffrn_reflns_reduction_process 62518
_reflns_number_total 5027
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_theta_full 20.82
_reflns_number_gt 4303
_reflns_threshold_expression I>3\s(I)
_computing_data_collection 'SMART (Siemens, 1995)'
_computing_cell_refinement 'SAINT (Siemens, 1995)'
_computing_data_reduction 'SAINT (Siemens, 1995)'
_computing_structure_solution
;
SIR97 (Altomare et al., 1997 ), KRYSTAL
;
_computing_structure_refinement 'modified ORFLS(1962), KRYSTAL'
_computing_molecular_graphics
;
ORTEP-III (Burnett & Johnson, 1996), KRYSTAL
;
_computing_publication_material KRYSTAL
_atom_type_scat_source IntTabIV
#===================================
# 8. REFINEMENT DATA
_refine_special_details
; The crystals available were small and poorly diffracting. Both one triflate-
group and one phenyl show large thermal motion. The largest peaks and holes in
the final difference map are found in these regions.
The hydrogen atoms on nitrogen were located from a difference fourier map and
their coordinates refined.
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^
where A = 0.05 and B = 0.25
;
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method
;
Type 1 Lorentzian isotropic (Becker and Coppens, 1974)
;
_refine_ls_extinction_coef 1396(144)
_refine_ls_abs_structure_details
; The least squares refinement included a factor according to Rogers (1981).
4303 significant reflections were used, including 1598 Bijvoet pairs.
;
_refine_ls_abs_structure_Rogers 1.02(24)
_refine_ls_number_reflns 4303
_refine_ls_number_parameters 279
_refine_ls_number_restraints 0
_refine_ls_number_constraints 0
_refine_ls_R_factor_gt 0.064
_refine_ls_wR_factor_ref 0.081
_refine_ls_goodness_of_fit_ref 1.70
_refine_ls_shift/su_max 0.0006
_refine_ls_shift/su_mean 0.00005
_refine_diff_density_max 0.8(1)
_refine_diff_density_min -1.1(1)
#==========================================
# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
S1 0.77079(15) 0.59057(12) 0.34188(2) 0.0511(9) Uij
S2 1.03508(9) 0.72498(8) 0.25645(2) 0.0195(5) Uij
F1 0.9135(4) 0.5298(3) 0.37058(6) 0.069(3) Uij
F2 0.8301(5) 0.4046(3) 0.33810(8) 0.099(4) Uij
F3 0.9970(4) 0.6026(3) 0.33370(7) 0.074(3) Uij
F4 1.2513(3) 0.7674(4) 0.27836(7) 0.069(3) Uij
F5 1.0915(3) 0.5691(3) 0.28185(6) 0.048(2) Uij
F6 1.1948(4) 0.6353(4) 0.24651(6) 0.070(4) Uij
O1 0.6628(4) 0.5134(4) 0.35866(7) 0.071(3) Uij
O2 0.7526(4) 0.5866(3) 0.31516(6) 0.055(3) Uij
O3 0.9866(3) 0.7471(3) 0.27948(5) 0.028(2) Uij
O4 1.1066(3) 0.8296(2) 0.23891(5) 0.029(2) Uij
N1 0.8479(4) 0.7381(4) 0.35141(7) 0.037(3) Uij
N2 0.9209(3) 0.6036(3) 0.24172(6) 0.023(2) Uij
C1 0.9312(4) 0.8567(4) 0.33600(7) 0.026(3) Uij
C2 1.0625(4) 0.9422(4) 0.34920(8) 0.031(3) Uij
C3 1.0694(5) 1.0147(5) 0.37072(9) 0.042(4) Uij
C4 1.1896(6) 1.0970(6) 0.38175(11) 0.053(4) Uij
C5 1.3062(6) 1.1111(6) 0.37225(12) 0.056(4) Uij
C6 1.2983(5) 1.0369(7) 0.35134(12) 0.057(5) Uij
C7 1.1788(5) 0.9540(5) 0.33988(9) 0.041(4) Uij
C8 0.8844(8) 0.5290(5) 0.34633(11) 0.070(6) Uij
C11 0.8075(3) 0.4866(3) 0.25355(7) 0.022(2) Uij
C12 0.8035(4) 0.3598(4) 0.24542(8) 0.028(3) Uij
C13 0.8056(5) 0.3309(4) 0.22031(9) 0.037(3) Uij
C14 0.7923(5) 0.2105(5) 0.21310(11) 0.048(4) Uij
C15 0.7741(5) 0.1170(5) 0.23129(13) 0.053(4) Uij
C16 0.7724(5) 0.1456(5) 0.25635(12) 0.050(4) Uij
C17 0.7855(4) 0.2653(4) 0.26356(10) 0.040(3) Uij
C18 1.1516(4) 0.6714(5) 0.26605(9) 0.037(3) Uij
H1n 0.852(6) 0.744(6) 0.3645(9) 0.043 Uiso
H2n 0.931(5) 0.608(5) 0.2284(9) 0.027 Uiso
H1 0.9466 0.8297 0.31996 0.031 Uiso
H3 0.9908 1.0078 0.37765 0.051 Uiso
H4 1.1927 1.1464 0.39624 0.063 Uiso
H5 1.3892 1.1698 0.37984 0.067 Uiso
H6 1.3771 1.0422 0.34480 0.069 Uiso
H7 1.1759 0.9043 0.32533 0.049 Uiso
H11 0.8161 0.4947 0.27142 0.027 Uiso
H13 0.8163 0.3935 0.20773 0.043 Uiso
H14 0.7949 0.1919 0.19559 0.057 Uiso
H15 0.7632 0.0340 0.22625 0.064 Uiso
H16 0.7622 0.0821 0.26876 0.060 Uiso
H17 0.7819 0.2836 0.28094 0.048 Uiso
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0625(9) 0.0293(6) 0.0286(6) -0.0016(6) 0.0085(5) 0.0025(5)
S2 0.0206(4) 0.0166(4) 0.0171(4) 0.0062(3) -0.0001(3) 0.0006(3)
F1 0.107(3) 0.050(2) 0.051(2) 0.039(2) 0.006(2) 0.012(2)
F2 0.175(5) 0.038(2) 0.078(3) 0.047(3) 0.015(3) 0.001(2)
F3 0.109(3) 0.055(2) 0.074(2) 0.052(2) 0.031(2) 0.016(2)
F4 0.038(2) 0.063(2) 0.084(3) 0.009(2) -0.032(2) 0.009(2)
F5 0.056(2) 0.042(2) 0.053(2) 0.031(1) -0.003(1) 0.016(1)
F6 0.074(2) 0.127(3) 0.055(2) 0.086(2) 0.012(2) 0.014(2)
O1 0.069(3) 0.051(2) 0.042(2) -0.009(2) 0.009(2) 0.009(2)
O2 0.073(3) 0.030(2) 0.029(2) 0.001(2) 0.000(2) -0.004(1)
O3 0.031(1) 0.027(1) 0.020(1) 0.010(1) 0.001(1) -0.001(1)
O4 0.031(1) 0.020(1) 0.020(1) 0.002(1) 0.002(1) 0.006(1)
N1 0.042(2) 0.035(2) 0.018(2) 0.008(2) 0.012(2) -0.001(2)
N2 0.025(2) 0.014(1) 0.020(2) 0.004(1) -0.002(1) 0.001(1)
C1 0.036(2) 0.028(2) 0.013(2) 0.015(2) 0.009(1) 0.001(1)
C2 0.040(2) 0.027(2) 0.027(2) 0.017(2) 0.003(2) 0.002(2)
C3 0.045(3) 0.056(3) 0.038(3) 0.035(2) -0.009(2) -0.009(2)
C4 0.057(3) 0.050(3) 0.066(4) 0.038(3) -0.029(3) -0.018(3)
C5 0.045(3) 0.056(3) 0.075(4) 0.029(3) -0.020(3) 0.002(3)
C6 0.033(3) 0.074(4) 0.072(4) 0.033(3) 0.010(3) 0.022(3)
C7 0.048(3) 0.042(3) 0.039(2) 0.027(2) 0.012(2) 0.012(2)
C8 0.118(6) 0.031(3) 0.047(3) 0.027(3) 0.017(4) 0.009(2)
C11 0.020(2) 0.011(1) 0.027(2) 0.001(1) -0.004(1) 0.004(1)
C12 0.027(2) 0.016(2) 0.039(2) 0.009(2) -0.008(2) -0.002(2)
C13 0.042(3) 0.025(2) 0.045(3) 0.019(2) -0.006(2) -0.001(2)
C14 0.053(3) 0.031(2) 0.064(3) 0.024(2) -0.005(3) -0.013(2)
C15 0.049(3) 0.022(2) 0.097(5) 0.025(2) -0.004(3) -0.006(2)
C16 0.040(3) 0.030(2) 0.086(4) 0.022(2) 0.008(3) 0.021(3)
C17 0.036(2) 0.028(2) 0.056(3) 0.016(2) -0.004(2) 0.012(2)
C18 0.025(2) 0.042(3) 0.043(3) 0.017(2) -0.002(2) 0.009(2)
#=================================
# 10. MOLECULAR GEOMETRY
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 O2 1.424(4) . .
S1 O1 1.429(4) . .
S1 N1 1.570(4) . .
S1 C8 1.807(8) . .
S2 O3 1.417(3) . .
S2 O4 1.421(3) . .
S2 N2 1.577(3) . .
S2 C18 1.824(4) . .
F1 C8 1.323(7) . .
F2 C8 1.330(7) . .
F3 C8 1.331(8) . .
F4 C18 1.311(5) . .
F5 C18 1.331(5) . .
F6 C18 1.306(6) . .
N1 C1 1.472(5) . .
N2 C11 1.480(4) . .
C1 C2 1.513(6) . .
C1 C1 1.529(9) . 7_555
C2 C7 1.381(7) . .
C2 C3 1.393(6) . .
C3 C4 1.369(7) . .
C4 C5 1.378(8) . .
C5 C6 1.376(9) . .
C6 C7 1.375(8) . .
C11 C12 1.514(5) . .
C11 C11 1.542(7) . 11_655
C12 C13 1.372(7) . .
C12 C17 1.392(6) . .
C13 C14 1.383(6) . .
C14 C15 1.386(8) . .
C15 C16 1.367(8) . .
C16 C17 1.377(7) . .
N1 H1n 0.69(5) . .
N2 H2n 0.709(45) . .
C1 H1 0.95 . .
C3 H3 0.95 . .
C4 H4 0.95 . .
C5 H5 0.95 . .
C6 H6 0.95 . .
C7 H7 0.95 . .
C11 H11 0.95 . .
C13 H13 0.95 . .
C14 H14 0.95 . .
C15 H15 0.95 . .
C16 H16 0.95 . .
C17 H17 0.95 . .
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_2
_geom_angle_site_symmetry_3
O1 S1 O2 121.6(3) . . .
N1 S1 O2 110.3(2) . . .
C8 S1 O2 104.1(3) . . .
N1 S1 O1 109.3(2) . . .
C8 S1 O1 105.0(3) . . .
C8 S1 N1 105.1(3) . . .
O4 S2 O3 121.3(2) . . .
N2 S2 O3 110.6(2) . . .
C18 S2 O3 104.7(2) . . .
N2 S2 O4 108.4(2) . . .
C18 S2 O4 104.9(2) . . .
C18 S2 N2 105.6(2) . . .
S1 N1 C1 126.6(3) . . .
S2 N2 C11 125.4(3) . . .
C2 C1 N1 109.7(3) . . .
C1 C1 N1 109.8(3) 7_555 . .
C1 C1 C2 112.6(3) 7_555 . .
C3 C2 C7 118.3(5) . . .
C1 C2 C7 121.2(4) . . .
C1 C2 C3 120.5(4) . . .
C2 C3 C4 120.0(5) . . .
C5 C4 C3 122.0(5) . . .
C4 C5 C6 117.7(5) . . .
C5 C6 C7 121.4(5) . . .
C2 C7 C6 120.7(5) . . .
F2 C8 F1 107.7(5) . . .
F3 C8 F1 108.3(6) . . .
S1 C8 F1 111.0(5) . . .
F3 C8 F2 108.4(5) . . .
S1 C8 F2 110.2(6) . . .
S1 C8 F3 111.1(4) . . .
C12 C11 N2 110.9(3) . . .
C11 C11 N2 108.4(3) 11_655 . .
C11 C11 C12 111.9(2) 11_655 . .
C17 C12 C13 119.0(4) . . .
C11 C12 C13 121.2(4) . . .
C11 C12 C17 119.5(4) . . .
C14 C13 C12 120.5(4) . . .
C15 C14 C13 120.0(5) . . .
C14 C15 C16 119.6(4) . . .
C17 C16 C15 120.4(5) . . .
C12 C17 C16 120.3(5) . . .
F4 C18 F6 110.3(4) . . .
F5 C18 F6 108.8(4) . . .
S2 C18 F6 111.2(3) . . .
F5 C18 F4 107.3(4) . . .
S2 C18 F4 109.8(3) . . .
S2 C18 F5 109.4(3) . . .
C1 N1 H1n 119(5) . . .
S1 N1 H1n 114(5) . . .
C11 N2 H2n 122(4) . . .
S2 N2 H2n 113(4) . . .
N1 C1 H1 109.1 . . .
C2 C1 H1 109.5 . . .
C1 C1 H1 106.1 7_555 . .
C4 C3 H3 119.9 . . .
C2 C3 H3 120.1 . . .
C3 C4 H4 119.0 . . .
C5 C4 H4 119.0 . . .
C6 C5 H5 121.0 . . .
C4 C5 H5 121.3 . . .
C7 C6 H6 119.2 . . .
C5 C6 H6 119.4 . . .
C6 C7 H7 119.9 . . .
C2 C7 H7 119.5 . . .
N2 C11 H11 109.1 . . .
C12 C11 H11 109.3 . . .
C11 C11 H11 107.2 11_655 . .
C12 C13 H13 120.1 . . .
C14 C13 H13 119.4 . . .
C13 C14 H14 119.8 . . .
C15 C14 H14 120.2 . . .
C16 C15 H15 120.7 . . .
C14 C15 H15 119.7 . . .
C15 C16 H16 119.3 . . .
C17 C16 H16 120.2 . . .
C16 C17 H17 120.0 . . .
C12 C17 H17 119.7 . . .
loop_
_publ_manuscript_incl_extra_item
'_geom_bond_atom_site_label_D'
'_geom_bond_atom_site_label_H'
'_geom_contact_atom_site_label_A'
'_geom_bond_distance_DH'
'_geom_contact_distance_HA'
'_geom_contact_distance_DA'
'_geom_angle_DHA'
'_geom_contact_site_symmetry_A'
loop_
_geom_bond_atom_site_label_D
_geom_bond_atom_site_label_H
_geom_contact_atom_site_label_A
_geom_bond_distance_DH
_geom_contact_distance_HA
_geom_contact_distance_DA
_geom_angle_DHA
_geom_contact_site_symmetry_A
N1 H1n O4 0.69(5) 2.18(5) 2.867(4) 169(6) 5_565
N2 H2n O2 0.71(5) 2.52(5) 3.144(5) 148(5) 11_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C1 C1 N1 -64.1(6) . . 7_555 7_555
N2 C11 C11 N2 -65.7(5) . . 11_655 11_655
S1 N1 C1 C1 104.1(5) . . . 7_555
S2 N2 C11 C11 114.4(4) . . . 11_655