# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2004

data_global

_publ_contact_author_email       WENTRUP@UQ.EDU.AU

_publ_contact_author_name        'Prof Curt Wentrup'
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_publ_contact_author_address     
;
Brisbane
4072
AUSTRALIA
;

_publ_section_title              
;
Diazepins.2.Synthesis of 1,3-diazepines and ring
contraction to cyanopyrroles
;

loop_
_publ_author_name
'Curt Wentrup'
'Paul V. Bernhardt'
'Ales Reisinger'

data_cw17298
_database_code_CSD               218060

_audit_creation_date             2003-08-20T12:19:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C6 H7 Cl1 N4 O1'
_chemical_formula_structural     'C6 H7 CL N4 O'
_chemical_formula_sum            'C7 H7 Cl N4 O'
_chemical_formula_weight         198.62
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.792(1)
_cell_length_b                   10.213(2)
_cell_length_c                   11.809(3)
_cell_angle_alpha                105.66(2)
_cell_angle_beta                 94.91(3)
_cell_angle_gamma                102.04(2)
_cell_volume                     874.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.787
_cell_measurement_theta_max      14.048
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_factor_muR        0.039
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   5
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_correction_T_ave  0.9334

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.75463E-1
_diffrn_orient_matrix_ub_12      0.74551E-1
_diffrn_orient_matrix_ub_13      -0.26687E-1
_diffrn_orient_matrix_ub_21      -0.109091
_diffrn_orient_matrix_ub_22      0.24029E-1
_diffrn_orient_matrix_ub_23      -0.31111E-1
_diffrn_orient_matrix_ub_31      0.5172E-2
_diffrn_orient_matrix_ub_32      0.06959
_diffrn_orient_matrix_ub_33      0.79047E-1
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_standards_number         3
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        1
_diffrn_standards_decay_corr_max 1.009
_diffrn_standards_decay_corr_min 0.963
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 -2 2
0 5 -5
-1 1 5

_diffrn_reflns_number            3313
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3068
_reflns_number_gt                1429
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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^)+(0.0546P)^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     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef       0.015(2)
_refine_ls_number_reflns         3068
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
#                   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
N1 N 0.1817(4) 0.4136(3) 0.8017(3) 0.0580(8) Uani 1 1 d . . .
N2 N 0.1193(4) 0.5171(3) 0.7763(3) 0.0628(9) Uani 1 1 d . . .
N3 N 0.0825(4) 0.4980(3) 0.6620(3) 0.0639(9) Uani 1 1 d . . .
N4 N 0.1261(4) 0.3753(3) 0.6100(3) 0.0504(8) Uani 1 1 d . . .
O1 O 0.2947(3) 0.1514(2) 0.7520(2) 0.0604(7) Uani 1 1 d . . .
Cl1 Cl 0.15313(17) 0.10715(12) 0.31013(8) 0.0825(4) Uani 1 1 d . . .
C5 C 0.1110(5) 0.3136(4) 0.4897(3) 0.0569(10) Uani 1 1 d . . .
H5 H 0.0688 0.3524 0.4335 0.068 Uiso 1 1 calc R . .
C6 C 0.1622(5) 0.1922(4) 0.4596(3) 0.0541(10) Uani 1 1 d . . .
C7 C 0.2251(5) 0.1310(4) 0.5429(3) 0.0533(10) Uani 1 1 d . . .
H7 H 0.2583 0.0467 0.5175 0.064 Uiso 1 1 calc R . .
C8 C 0.2367(5) 0.1961(4) 0.6610(3) 0.0518(10) Uani 1 1 d . . .
C8A C 0.1850(5) 0.3243(4) 0.6963(3) 0.0455(9) Uani 1 1 d . . .
C9 C 0.3437(6) 0.0187(4) 0.7190(3) 0.0647(11) Uani 1 1 d . . .
H9A H 0.4452 0.0256 0.677 0.078 Uiso 1 1 calc R . .
H9B H 0.2458 -0.0537 0.6676 0.078 Uiso 1 1 calc R . .
C10 C 0.3887(6) -0.0157(5) 0.8319(4) 0.0847(14) Uani 1 1 d . . .
H10A H 0.4866 0.0562 0.8816 0.127 Uiso 1 1 calc R . .
H10B H 0.4206 -0.1041 0.8134 0.127 Uiso 1 1 calc R . .
H10C H 0.2876 -0.0212 0.8731 0.127 Uiso 1 1 calc R . .
N1' N -0.2936(4) 0.2161(3) 0.5819(3) 0.0577(9) Uani 1 1 d . . .
N2' N -0.3435(4) 0.2541(3) 0.4854(3) 0.0655(9) Uani 1 1 d . . .
N3' N -0.3913(4) 0.3721(3) 0.5139(3) 0.0640(9) Uani 1 1 d . . .
N4' N -0.3711(4) 0.4147(3) 0.6353(2) 0.0488(8) Uani 1 1 d . . .
C5' C -0.4021(5) 0.5349(4) 0.7062(3) 0.0552(10) Uani 1 1 d . . .
H5' H -0.4437 0.5988 0.6748 0.066 Uiso 1 1 calc R . .
C6' C -0.3690(5) 0.5549(4) 0.8237(3) 0.0533(10) Uani 1 1 d . . .
C7' C -0.3061(5) 0.4596(4) 0.8731(3) 0.0542(10) Uani 1 1 d . . .
H7' H -0.2851 0.4779 0.9552 0.065 Uiso 1 1 calc R . .
C8' C -0.2762(5) 0.3403(4) 0.8000(3) 0.0509(10) Uani 1 1 d . . .
C8A' C -0.3103(5) 0.3180(4) 0.6754(3) 0.0466(9) Uani 1 1 d . . .
C9' C -0.1457(5) 0.2694(4) 0.9559(3) 0.0619(11) Uani 1 1 d . . .
H9'1 H -0.2418 0.2751 1.0026 0.074 Uiso 1 1 calc R . .
H9'2 H -0.057 0.3577 0.9842 0.074 Uiso 1 1 calc R . .
C10' C -0.0662(6) 0.1527(5) 0.9672(3) 0.0724(12) Uani 1 1 d . . .
H10D H -0.1551 0.0659 0.9389 0.109 Uiso 1 1 calc R . .
H10E H -0.021 0.1684 1.0492 0.109 Uiso 1 1 calc R . .
H10F H 0.029 0.1484 0.9209 0.109 Uiso 1 1 calc R . .
O1' O -0.2117(3) 0.2406(2) 0.8314(2) 0.0594(7) Uani 1 1 d . . .
Cl1' Cl -0.40665(15) 0.70242(11) 0.91993(9) 0.0752(4) Uani 1 1 d . . .

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 0.069(2) 0.057(2) 0.0446(18) 0.0052(16) 0.0068(15) 0.0219(18)
N2 0.075(2) 0.058(2) 0.054(2) 0.0059(17) 0.0124(18) 0.0240(19)
N3 0.078(2) 0.060(2) 0.057(2) 0.0102(17) 0.0112(18) 0.0306(19)
N4 0.054(2) 0.0484(18) 0.0477(19) 0.0073(16) 0.0084(15) 0.0176(16)
O1 0.0808(19) 0.0573(16) 0.0457(15) 0.0120(13) 0.0057(13) 0.0280(15)
Cl1 0.1124(10) 0.0869(8) 0.0406(6) 0.0001(5) 0.0090(6) 0.0332(7)
C5 0.067(3) 0.063(3) 0.040(2) 0.0116(19) 0.0063(19) 0.021(2)
C6 0.063(3) 0.058(2) 0.036(2) 0.0062(18) 0.0071(18) 0.013(2)
C7 0.063(3) 0.047(2) 0.047(2) 0.0042(18) 0.0088(19) 0.019(2)
C8 0.055(3) 0.051(2) 0.047(2) 0.011(2) 0.0071(18) 0.013(2)
C8A 0.050(2) 0.046(2) 0.040(2) 0.0101(18) 0.0072(17) 0.0129(19)
C9 0.080(3) 0.056(2) 0.064(3) 0.016(2) 0.014(2) 0.028(2)
C10 0.114(4) 0.084(3) 0.079(3) 0.042(3) 0.020(3) 0.046(3)
N1' 0.073(2) 0.0544(19) 0.0461(19) 0.0107(16) 0.0087(16) 0.0211(18)
N2' 0.083(3) 0.066(2) 0.045(2) 0.0087(17) 0.0063(17) 0.027(2)
N3' 0.085(3) 0.067(2) 0.0410(19) 0.0097(17) 0.0088(17) 0.028(2)
N4' 0.053(2) 0.0515(18) 0.0418(18) 0.0130(15) 0.0050(14) 0.0153(16)
C5' 0.061(3) 0.047(2) 0.056(3) 0.008(2) 0.005(2) 0.021(2)
C6' 0.056(3) 0.048(2) 0.053(2) 0.0055(19) 0.0059(19) 0.016(2)
C7' 0.063(3) 0.056(2) 0.039(2) 0.0068(18) 0.0046(18) 0.014(2)
C8' 0.052(2) 0.052(2) 0.044(2) 0.0107(19) 0.0023(18) 0.010(2)
C8A' 0.053(2) 0.044(2) 0.041(2) 0.0083(18) 0.0058(17) 0.0147(19)
C9' 0.073(3) 0.072(3) 0.041(2) 0.017(2) 0.000(2) 0.020(2)
C10' 0.085(3) 0.092(3) 0.053(2) 0.031(2) 0.007(2) 0.038(3)
O1' 0.0808(19) 0.0572(15) 0.0426(14) 0.0121(12) 0.0021(13) 0.0281(15)
Cl1' 0.0920(9) 0.0640(7) 0.0657(7) 0.0011(5) 0.0129(6) 0.0340(6)

#----------------------------------------------------------------------------#
#                   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
N1 C8A 1.336(4) . ?
N1 N2 1.342(4) . ?
N2 N3 1.309(4) . ?
N3 N4 1.364(4) . ?
N4 C8A 1.351(4) . ?
N4 C5 1.374(4) . ?
O1 C8 1.355(4) . ?
O1 C9 1.445(4) . ?
Cl1 C6 1.732(3) . ?
C5 C6 1.347(5) . ?
C6 C7 1.406(5) . ?
C7 C8 1.359(4) . ?
C8 C8A 1.416(5) . ?
C9 C10 1.500(5) . ?
N1' C8A' 1.335(4) . ?
N1' N2' 1.351(4) . ?
N2' N3' 1.301(4) . ?
N3' N4' 1.365(4) . ?
N4' C8A' 1.355(4) . ?
N4' C5' 1.368(4) . ?
C5' C6' 1.341(5) . ?
C6' C7' 1.408(5) . ?
C6' Cl1' 1.722(4) . ?
C7' C8' 1.368(5) . ?
C8' O1' 1.345(4) . ?
C8' C8A' 1.419(4) . ?
C9' O1' 1.445(4) . ?
C9' C10' 1.483(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
C8A N1 N2 105.2(3) . . ?
N3 N2 N1 113.0(3) . . ?
N2 N3 N4 104.6(3) . . ?
C8A N4 N3 108.7(3) . . ?
C8A N4 C5 125.8(3) . . ?
N3 N4 C5 125.5(3) . . ?
C8 O1 C9 116.1(3) . . ?
C6 C5 N4 114.6(3) . . ?
C5 C6 C7 123.7(3) . . ?
C5 C6 Cl1 118.5(3) . . ?
C7 C6 Cl1 117.8(3) . . ?
C8 C7 C6 119.4(3) . . ?
O1 C8 C7 126.6(3) . . ?
O1 C8 C8A 114.7(3) . . ?
C7 C8 C8A 118.7(3) . . ?
N1 C8A N4 108.4(3) . . ?
N1 C8A C8 133.7(3) . . ?
N4 C8A C8 117.9(3) . . ?
O1 C9 C10 107.1(3) . . ?
C8A' N1' N2' 105.5(3) . . ?
N3' N2' N1' 112.3(3) . . ?
N2' N3' N4' 105.6(3) . . ?
C8A' N4' N3' 108.1(3) . . ?
C8A' N4' C5' 124.9(3) . . ?
N3' N4' C5' 127.0(3) . . ?
C6' C5' N4' 115.8(3) . . ?
C5' C6' C7' 123.0(3) . . ?
C5' C6' Cl1' 119.1(3) . . ?
C7' C6' Cl1' 117.8(3) . . ?
C8' C7' C6' 119.9(3) . . ?
O1' C8' C7' 127.9(3) . . ?
O1' C8' C8A' 114.4(3) . . ?
C7' C8' C8A' 117.6(3) . . ?
N1' C8A' N4' 108.5(3) . . ?
N1' C8A' C8' 132.8(3) . . ?
N4' C8A' C8' 118.7(3) . . ?
O1' C9' C10' 107.2(3) . . ?
C8' O1' C9' 116.8(3) . . ?

#===END

data_1411ar1
_database_code_CSD               218061

_audit_creation_date             2003-08-20T15:26:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C10 H17 N3 O1'
_chemical_formula_structural     'C10 H17 N3 O'
_chemical_formula_sum            'C10 H17 N3 O'
_chemical_formula_weight         195.27
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   11.185(2)
_cell_length_b                   8.1266(4)
_cell_length_c                   12.711(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.343(9)
_cell_angle_gamma                90
_cell_volume                     1102.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10.102
_cell_measurement_theta_max      14.234
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_factor_muR        0
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   1
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_absorpt_correction_T_min  0.9343
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_correction_T_ave  0.9678

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.74943E-1
_diffrn_orient_matrix_ub_12      0.16684E-1
_diffrn_orient_matrix_ub_13      0.65596E-1
_diffrn_orient_matrix_ub_21      -0.54992E-1
_diffrn_orient_matrix_ub_22      -0.2482E-2
_diffrn_orient_matrix_ub_23      0.49255E-1
_diffrn_orient_matrix_ub_31      0.11429E-1
_diffrn_orient_matrix_ub_32      -0.12194
_diffrn_orient_matrix_ub_33      0.7929E-2
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_standards_number         3
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        2
_diffrn_standards_decay_corr_max 1.03
_diffrn_standards_decay_corr_min 0.968
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 0 7
-6 -1 -1
-2 -4 3

_diffrn_reflns_number            3648
_diffrn_reflns_av_R_equivalents  0.002
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             1939
_reflns_number_gt                1510
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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^)+(0.0559P)^2^+0.3197P] 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         1939
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   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'

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 0.69003(14) -0.15250(17) 0.66573(12) 0.0502(4) Uani 1 1 d . . .
C2 C 0.70742(15) -0.0433(2) 0.74234(13) 0.0442(4) Uani 1 1 d . . .
N3 N 0.70294(13) -0.05194(18) 0.84807(11) 0.0483(4) Uani 1 1 d . . .
C4 C 0.61491(16) -0.1355(2) 0.87250(13) 0.0450(4) Uani 1 1 d . . .
C5 C 0.50634(16) -0.2016(2) 0.78207(15) 0.0568(5) Uani 1 1 d . . .
H5A H 0.4415 -0.2422 0.8118 0.068 Uiso 1 1 calc R . .
H5B H 0.4709 -0.1164 0.7283 0.068 Uiso 1 1 calc R . .
C6 C 0.55796(19) -0.3380(2) 0.73042(16) 0.0594(5) Uani 1 1 d . . .
H6 H 0.5309 -0.4455 0.7342 0.071 Uiso 1 1 calc R . .
C7 C 0.64247(19) -0.3060(2) 0.67911(16) 0.0574(5) Uani 1 1 d . . .
H7 H 0.6729 -0.3953 0.6491 0.069 Uiso 1 1 calc R . .
O8 O 0.75354(12) 0.10616(15) 0.72620(9) 0.0543(4) Uani 1 1 d . . .
C9 C 0.77388(16) 0.1418(2) 0.62104(13) 0.0476(4) Uani 1 1 d . . .
H9 H 0.8083 0.0446 0.5948 0.057 Uiso 1 1 calc R . .
C10 C 0.86856(19) 0.2787(3) 0.64398(17) 0.0617(5) Uani 1 1 d . . .
H10A H 0.9445 0.2425 0.697 0.093 Uiso 1 1 calc R . .
H10B H 0.8359 0.3722 0.6726 0.093 Uiso 1 1 calc R . .
H10C H 0.8857 0.309 0.5769 0.093 Uiso 1 1 calc R . .
C11 C 0.65315(18) 0.1914(3) 0.53759(16) 0.0625(5) Uani 1 1 d . . .
H11A H 0.595 0.1014 0.5252 0.094 Uiso 1 1 calc R . .
H11B H 0.6688 0.2199 0.4696 0.094 Uiso 1 1 calc R . .
H11C H 0.6185 0.2847 0.5646 0.094 Uiso 1 1 calc R . .
N12 N 0.62423(14) -0.16224(19) 0.97870(12) 0.0533(4) Uani 1 1 d . . .
C13 C 0.73169(19) -0.1009(3) 1.06516(15) 0.0633(5) Uani 1 1 d . . .
H13A H 0.7036 -0.0282 1.1124 0.095 Uiso 1 1 calc R . .
H13B H 0.7863 -0.0423 1.0326 0.095 Uiso 1 1 calc R . .
H13C H 0.7761 -0.1917 1.1075 0.095 Uiso 1 1 calc R . .
C14 C 0.53379(19) -0.2532(3) 1.01747(18) 0.0673(6) Uani 1 1 d . . .
H14A H 0.577 -0.3298 1.0734 0.101 Uiso 1 1 calc R . .
H14B H 0.4781 -0.3121 0.957 0.101 Uiso 1 1 calc R . .
H14C H 0.4864 -0.178 1.0476 0.101 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 0.0635(9) 0.0380(8) 0.0472(8) -0.0042(6) 0.0133(7) -0.0003(7)
C2 0.0496(9) 0.0394(9) 0.0409(9) 0.0021(7) 0.0093(7) -0.0042(7)
N3 0.0596(9) 0.0456(8) 0.0380(7) 0.0002(6) 0.0119(6) -0.0127(7)
C4 0.0511(9) 0.0366(9) 0.0447(9) 0.0043(7) 0.0103(7) -0.0002(7)
C5 0.0466(10) 0.0599(12) 0.0567(11) 0.0075(9) 0.0045(8) -0.0052(9)
C6 0.0660(12) 0.0402(10) 0.0582(11) 0.0032(8) -0.0024(9) -0.0126(9)
C7 0.0709(12) 0.0348(9) 0.0582(11) -0.0047(8) 0.0070(10) 0.0042(9)
O8 0.0812(9) 0.0440(7) 0.0422(6) -0.0043(5) 0.0252(6) -0.0167(6)
C9 0.0594(10) 0.0467(10) 0.0416(9) 0.0006(7) 0.0225(8) -0.0022(8)
C10 0.0632(12) 0.0614(12) 0.0648(12) 0.0070(10) 0.0254(10) -0.0091(10)
C11 0.0633(12) 0.0663(13) 0.0574(11) 0.0070(10) 0.0174(9) -0.0023(10)
N12 0.0596(9) 0.0538(9) 0.0478(8) 0.0067(7) 0.0181(7) -0.0106(7)
C13 0.0711(12) 0.0762(14) 0.0412(9) 0.0010(9) 0.0145(9) -0.0111(11)
C14 0.0698(13) 0.0687(14) 0.0694(13) 0.0143(10) 0.0298(11) -0.0078(10)

#----------------------------------------------------------------------------#
#                   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
N1 C2 1.288(2) . ?
N1 C7 1.387(2) . ?
C2 O8 1.359(2) . ?
C2 N3 1.362(2) . ?
N3 C4 1.307(2) . ?
C4 N12 1.340(2) . ?
C4 C5 1.501(2) . ?
C5 C6 1.490(3) . ?
C6 C7 1.324(3) . ?
O8 C9 1.4504(19) . ?
C9 C11 1.502(3) . ?
C9 C10 1.503(3) . ?
N12 C14 1.453(2) . ?
N12 C13 1.454(2) . ?

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 C7 120.26(16) . . ?
N1 C2 O8 118.68(15) . . ?
N1 C2 N3 131.99(16) . . ?
O8 C2 N3 108.79(13) . . ?
C4 N3 C2 120.87(14) . . ?
N3 C4 N12 119.05(15) . . ?
N3 C4 C5 119.91(15) . . ?
N12 C4 C5 121.03(16) . . ?
C6 C5 C4 105.82(15) . . ?
C7 C6 C5 119.87(17) . . ?
C6 C7 N1 126.39(18) . . ?
C2 O8 C9 119.25(13) . . ?
O8 C9 C11 110.45(14) . . ?
O8 C9 C10 105.32(14) . . ?
C11 C9 C10 111.79(16) . . ?
C4 N12 C14 124.84(16) . . ?
C4 N12 C13 120.29(15) . . ?
C14 N12 C13 114.86(15) . . ?

#===END

data_1420ar2
_database_code_CSD               218062

_audit_creation_date             2003-08-20T16:34:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C25 H38 N6'
_chemical_formula_structural     'C25 H38 N6'
_chemical_formula_sum            'C25 H38 N6'
_chemical_formula_weight         422.61
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9884(9)
_cell_length_b                   11.953(1)
_cell_length_c                   12.2879(8)
_cell_angle_alpha                65.573(6)
_cell_angle_beta                 79.700(6)
_cell_angle_gamma                63.521(6)
_cell_volume                     1315.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10.322
_cell_measurement_theta_max      13.267
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.067
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_factor_muR        0
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   2
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_absorpt_correction_T_min  0.9501
_exptl_absorpt_correction_T_max  0.9988
_exptl_absorpt_correction_T_ave  0.9669

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      -0.38257E-1
_diffrn_orient_matrix_ub_12      0.53091E-1
_diffrn_orient_matrix_ub_13      0.52535E-1
_diffrn_orient_matrix_ub_21      -0.06044
_diffrn_orient_matrix_ub_22      -0.48146E-1
_diffrn_orient_matrix_ub_23      0.38726E-1
_diffrn_orient_matrix_ub_31      0.72255E-1
_diffrn_orient_matrix_ub_32      -0.71174E-1
_diffrn_orient_matrix_ub_33      0.61072E-1
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_standards_number         3
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        6
_diffrn_standards_decay_corr_max 1.115
_diffrn_standards_decay_corr_min 0.978
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 4 7
1 -4 3
2 -1 4

_diffrn_reflns_number            4922
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             4622
_reflns_number_gt                2840
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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^)+(0.0940P)^2^+0.3557P] 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         4622
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1826
_refine_ls_wR_factor_gt          0.1555
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   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'

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
N1A N -0.14872(18) 0.82595(18) 0.26699(15) 0.0532(5) Uani 1 1 d . A .
H1A H -0.2175 0.8933 0.2248 0.064 Uiso 1 1 d R . .
N2A N -0.1872(2) 0.90548(19) 0.42565(18) 0.0623(5) Uani 1 1 d . . .
N12A N 0.1448(2) 0.5842(2) 0.6007(2) 0.0789(7) Uani 1 1 d . . .
C2A C -0.1128(2) 0.8100(2) 0.37457(19) 0.0490(5) Uani 1 1 d . A .
C3A C 0.0025(2) 0.6902(2) 0.41107(19) 0.0495(5) Uani 1 1 d . . .
C4A C 0.0335(2) 0.6348(2) 0.3225(2) 0.0535(6) Uani 1 1 d . A .
H4A H 0.1029 0.5523 0.3254 0.064 Uiso 1 1 d R . .
C5A C -0.0609(2) 0.7210(2) 0.23368(19) 0.0515(5) Uani 1 1 d . . .
C6A C -0.2857(3) 0.8744(3) 0.5173(2) 0.0708(7) Uani 1 1 d . A .
H6A H -0.3538 0.9598 0.5225 0.085 Uiso 1 1 d R . .
C7A C -0.2219(4) 0.7825(4) 0.6411(3) 0.1123(12) Uani 1 1 d . . .
H7A1 H -0.1761 0.8226 0.6627 0.168 Uiso 1 1 d R A .
H7A2 H -0.1575 0.6966 0.6392 0.168 Uiso 1 1 d R . .
H7A3 H -0.2909 0.7701 0.6989 0.168 Uiso 1 1 d R . .
C8A C -0.3630(3) 0.8176(4) 0.4816(4) 0.1120(12) Uani 1 1 d . . .
H8A1 H -0.4041 0.8759 0.404 0.168 Uiso 1 1 d R A .
H8A2 H -0.4322 0.8056 0.5393 0.168 Uiso 1 1 d R . .
H8A3 H -0.299 0.7315 0.4798 0.168 Uiso 1 1 d R . .
C9A1 C -0.1255(5) 0.9863(5) 0.4262(4) 0.0648(15) Uiso 0.616(8) 1 d P A 1
H9A1 H -0.0513 0.9315 0.4851 0.078 Uiso 0.616(8) 1 d PR A 1
C9A2 C -0.1983(7) 1.0429(7) 0.3638(6) 0.061(2) Uiso 0.384(8) 1 d P A 2
H9A2 H -0.2731 1.0945 0.3056 0.073 Uiso 0.384(8) 1 d PR A 2
C10A C -0.0670(4) 1.0431(3) 0.3000(3) 0.0943(10) Uani 1 1 d . . .
H10A H -0.0031 0.9697 0.2775 0.141 Uiso 0.616(8) 1 d PR A 1
H10B H -0.0222 1.0952 0.3021 0.141 Uiso 0.616(8) 1 d PR A 1
H10C H -0.1401 1.0997 0.2427 0.141 Uiso 0.616(8) 1 d PR A 1
H10D H -0.0481 1.0015 0.2432 0.141 Uiso 0.384(8) 1 d PR A 2
H10E H 0.0064 0.9937 0.3568 0.141 Uiso 0.384(8) 1 d PR A 2
H10F H -0.0764 1.1346 0.2591 0.141 Uiso 0.384(8) 1 d PR A 2
C11A C -0.2258(3) 1.1098(3) 0.4551(3) 0.0956(10) Uani 1 1 d . . .
H11A H -0.2648 1.0801 0.5324 0.143 Uiso 0.616(8) 1 d PR A 1
H11B H -0.2968 1.1654 0.3958 0.143 Uiso 0.616(8) 1 d PR A 1
H11C H -0.1789 1.1609 0.4552 0.143 Uiso 0.616(8) 1 d PR A 1
H11D H -0.3087 1.1097 0.4965 0.143 Uiso 0.384(8) 1 d PR A 2
H11E H -0.235 1.2011 0.4139 0.143 Uiso 0.384(8) 1 d PR A 2
H11F H -0.1522 1.0602 0.5117 0.143 Uiso 0.384(8) 1 d PR A 2
C12A C 0.0800(2) 0.6331(2) 0.5169(2) 0.0577(6) Uani 1 1 d . A .
N1B N -0.27335(18) 0.65798(19) 0.17229(15) 0.0542(5) Uani 1 1 d . A .
H1B H -0.2371 0.595 0.2392 0.065 Uiso 1 1 d R . .
N2B N -0.4761(2) 0.6187(2) 0.19043(18) 0.0648(6) Uani 1 1 d . . .
N12B N -0.6171(3) 0.9156(3) -0.1224(2) 0.1012(9) Uani 1 1 d . . .
C2B C -0.3964(2) 0.6892(2) 0.1303(2) 0.0541(6) Uani 1 1 d . A .
C3B C -0.4147(2) 0.7948(2) 0.0212(2) 0.0600(6) Uani 1 1 d . . .
C4B C -0.3004(3) 0.8258(2) -0.0012(2) 0.0632(7) Uani 1 1 d . A .
H4B H -0.2862 0.893 -0.0681 0.076 Uiso 1 1 d R . .
C5B C -0.2137(2) 0.7390(2) 0.09355(19) 0.0546(6) Uani 1 1 d . . .
C6B C -0.5760(3) 0.6675(3) 0.2750(3) 0.0793(8) Uani 1 1 d . B .
H6B1 H -0.6354 0.6199 0.2982 0.095 Uiso 0.521(9) 1 d PR B 1
C7B1 C -0.6635(9) 0.8172(9) 0.2343(8) 0.123(3) Uiso 0.521(9) 1 d P B 1
H7B1 H -0.7124 0.8458 0.1633 0.185 Uiso 0.521(9) 1 d PR B 1
H7B2 H -0.6076 0.8653 0.2173 0.185 Uiso 0.521(9) 1 d PR B 1
H7B3 H -0.7269 0.8356 0.296 0.185 Uiso 0.521(9) 1 d PR B 1
C8B1 C -0.5023(7) 0.6312(9) 0.3919(7) 0.091(2) Uiso 0.521(9) 1 d P B 1
H8B1 H -0.4443 0.5364 0.4239 0.136 Uiso 0.521(9) 1 d PR B 1
H8B2 H -0.569 0.654 0.4502 0.136 Uiso 0.521(9) 1 d PR B 1
H8B3 H -0.4486 0.682 0.3723 0.136 Uiso 0.521(9) 1 d PR B 1
C7B2 C -0.7023(8) 0.7815(8) 0.1957(7) 0.097(3) Uiso 0.479(9) 1 d P B 2
H7B4 H -0.7324 0.7446 0.1552 0.145 Uiso 0.479(9) 1 d PR B 2
H7B5 H -0.6785 0.8522 0.1378 0.145 Uiso 0.479(9) 1 d PR B 2
H7B6 H -0.7741 0.8177 0.2452 0.145 Uiso 0.479(9) 1 d PR B 2
C8B2 C -0.5261(9) 0.7176(12) 0.3410(9) 0.115(3) Uiso 0.479(9) 1 d P B 2
H8B4 H -0.4487 0.6454 0.3892 0.172 Uiso 0.479(9) 1 d PR B 2
H8B5 H -0.5968 0.7536 0.3913 0.172 Uiso 0.479(9) 1 d PR B 2
H8B6 H -0.5003 0.7876 0.2845 0.172 Uiso 0.479(9) 1 d PR B 2
C9B1 C -0.4219(5) 0.4786(5) 0.2140(5) 0.0678(16) Uiso 0.614(8) 1 d P C 1
H9B1 H -0.3666 0.4278 0.2871 0.081 Uiso 0.614(8) 1 d PR C 1
C9B2 C -0.4766(8) 0.5305(8) 0.1375(7) 0.070(3) Uiso 0.386(8) 1 d P C 2
H9B2 H -0.5324 0.5845 0.0646 0.084 Uiso 0.386(8) 1 d PR C 2
C10B C -0.3334(4) 0.4471(4) 0.1093(3) 0.1051(11) Uani 1 1 d . . .
H10G H -0.2614 0.4758 0.0968 0.158 Uiso 0.614(8) 1 d PR C 1
H10H H -0.388 0.4943 0.0382 0.158 Uiso 0.614(8) 1 d PR C 1
H10I H -0.2952 0.3517 0.1278 0.158 Uiso 0.614(8) 1 d PR C 1
H10J H -0.2941 0.5059 0.0529 0.158 Uiso 0.386(8) 1 d PR C 2
H10K H -0.3357 0.3886 0.0755 0.158 Uiso 0.386(8) 1 d PR C 2
H10L H -0.2794 0.3937 0.1812 0.158 Uiso 0.386(8) 1 d PR C 2
C11B C -0.5338(4) 0.4298(4) 0.2286(4) 0.1087(12) Uani 1 1 d . . .
H11G H -0.5919 0.4475 0.2933 0.163 Uiso 0.614(8) 1 d PR C 1
H11H H -0.4934 0.3346 0.2457 0.163 Uiso 0.614(8) 1 d PR C 1
H11I H -0.5863 0.4772 0.1561 0.163 Uiso 0.614(8) 1 d PR C 1
H11J H -0.6249 0.4796 0.249 0.163 Uiso 0.386(8) 1 d PR C 2
H11K H -0.4781 0.3766 0.2994 0.163 Uiso 0.386(8) 1 d PR C 2
H11L H -0.5344 0.3715 0.1937 0.163 Uiso 0.386(8) 1 d PR C 2
C12B C -0.5280(3) 0.8603(3) -0.0573(2) 0.0737(8) Uani 1 1 d . C .
C13 C -0.0724(2) 0.7185(3) 0.1140(2) 0.0601(6) Uani 1 1 d . A .
C14 C 0.0300(3) 0.5820(3) 0.1090(3) 0.0855(9) Uani 1 1 d . . .
H14A H 0.1194 0.5704 0.1214 0.128 Uiso 1 1 d R A .
H14B H 0.0259 0.5794 0.0327 0.128 Uiso 1 1 d R . .
H14C H 0.0103 0.5107 0.171 0.128 Uiso 1 1 d R . .
C15 C -0.0406(3) 0.8335(4) 0.0155(2) 0.0936(10) Uani 1 1 d . . .
H15A H 0.0494 0.8196 0.0289 0.14 Uiso 1 1 d R A .
H15B H -0.1049 0.9191 0.0181 0.14 Uiso 1 1 d R . .
H15C H -0.045 0.8325 -0.0614 0.14 Uiso 1 1 d R . .
H6B2 H -0.609(7) 0.588(7) 0.335(6) 0.112 Uiso 0.479(9) 1 d P B 2

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
N1A 0.0442(10) 0.0517(11) 0.0479(10) -0.0089(9) -0.0174(8) -0.0094(9)
N2A 0.0643(12) 0.0534(11) 0.0640(12) -0.0215(10) 0.0051(10) -0.0227(10)
N12A 0.0765(15) 0.0771(15) 0.0668(14) -0.0060(11) -0.0357(12) -0.0245(12)
C2A 0.0463(11) 0.0453(12) 0.0468(12) -0.0097(10) -0.0107(9) -0.0148(10)
C3A 0.0435(11) 0.0468(12) 0.0482(12) -0.0085(10) -0.0153(9) -0.0133(10)
C4A 0.0434(12) 0.0498(12) 0.0603(14) -0.0179(11) -0.0109(10) -0.0122(10)
C5A 0.0453(12) 0.0567(13) 0.0505(12) -0.0170(11) -0.0065(10) -0.0201(11)
C6A 0.0617(15) 0.0664(16) 0.0745(17) -0.0255(14) 0.0049(13) -0.0211(13)
C7A 0.118(3) 0.128(3) 0.0676(19) -0.0117(19) 0.0084(19) -0.057(2)
C8A 0.074(2) 0.143(3) 0.143(3) -0.068(3) 0.024(2) -0.061(2)
C10A 0.113(3) 0.083(2) 0.097(2) -0.0304(18) 0.018(2) -0.059(2)
C11A 0.097(2) 0.081(2) 0.125(3) -0.057(2) 0.007(2) -0.0368(18)
C12A 0.0536(13) 0.0508(13) 0.0599(14) -0.0100(11) -0.0164(12) -0.0183(11)
N1B 0.0505(10) 0.0580(11) 0.0423(10) -0.0065(9) -0.0172(8) -0.0176(9)
N2B 0.0645(13) 0.0681(13) 0.0634(12) -0.0222(11) -0.0019(10) -0.0303(11)
N12B 0.0934(18) 0.0883(18) 0.0957(18) -0.0187(15) -0.0580(16) -0.0094(15)
C2B 0.0501(12) 0.0538(13) 0.0526(13) -0.0138(11) -0.0158(10) -0.0168(11)
C3B 0.0618(14) 0.0556(14) 0.0520(13) -0.0095(11) -0.0252(11) -0.0162(12)
C4B 0.0746(16) 0.0601(14) 0.0476(13) -0.0045(11) -0.0166(12) -0.0302(13)
C5B 0.0573(13) 0.0611(14) 0.0425(12) -0.0139(11) -0.0104(10) -0.0234(12)
C6B 0.0575(16) 0.082(2) 0.094(2) -0.0347(17) -0.0009(15) -0.0238(15)
C10B 0.113(3) 0.089(2) 0.128(3) -0.058(2) 0.018(2) -0.044(2)
C11B 0.115(3) 0.100(2) 0.135(3) -0.042(2) 0.012(2) -0.070(2)
C12B 0.0773(17) 0.0602(15) 0.0681(16) -0.0119(13) -0.0357(15) -0.0137(14)
C13 0.0545(13) 0.0798(17) 0.0483(13) -0.0225(12) -0.0023(10) -0.0305(13)
C14 0.0619(16) 0.122(3) 0.085(2) -0.0648(19) 0.0010(14) -0.0252(17)
C15 0.100(2) 0.138(3) 0.0587(16) -0.0188(17) 0.0020(16) -0.080(2)

#----------------------------------------------------------------------------#
#                   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
N1A C2A 1.360(3) . ?
N1A C5A 1.370(3) . ?
N2A C2A 1.394(3) . ?
N2A C9A1 1.409(5) . ?
N2A C9A2 1.453(7) . ?
N2A C6A 1.467(3) . ?
N12A C12A 1.141(3) . ?
C2A C3A 1.383(3) . ?
C3A C4A 1.414(3) . ?
C3A C12A 1.424(3) . ?
C4A C5A 1.360(3) . ?
C5A C13 1.512(3) . ?
C6A C8A 1.507(4) . ?
C6A C7A 1.525(4) . ?
C9A1 C11A 1.537(5) . ?
C9A1 C10A 1.562(5) . ?
C9A2 C10A 1.514(7) . ?
C9A2 C11A 1.547(7) . ?
N1B C5B 1.367(3) . ?
N1B C2B 1.369(3) . ?
N2B C2B 1.391(3) . ?
N2B C9B1 1.419(5) . ?
N2B C9B2 1.452(7) . ?
N2B C6B 1.465(4) . ?
N12B C12B 1.141(3) . ?
C2B C3B 1.379(3) . ?
C3B C4B 1.414(3) . ?
C3B C12B 1.424(3) . ?
C4B C5B 1.363(3) . ?
C5B C13 1.510(3) . ?
C6B C8B2 1.474(9) . ?
C6B C7B1 1.508(9) . ?
C6B C7B2 1.559(8) . ?
C6B C8B1 1.580(7) . ?
C9B1 C11B 1.535(5) . ?
C9B1 C10B 1.540(6) . ?
C9B2 C10B 1.511(8) . ?
C9B2 C11B 1.551(8) . ?
C13 C14 1.534(4) . ?
C13 C15 1.542(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
C2A N1A C5A 111.33(17) . . ?
C2A N2A C9A1 116.5(2) . . ?
C2A N2A C9A2 119.7(3) . . ?
C9A1 N2A C9A2 40.7(3) . . ?
C2A N2A C6A 116.1(2) . . ?
C9A1 N2A C6A 121.5(2) . . ?
C9A2 N2A C6A 121.1(3) . . ?
N1A C2A C3A 106.02(19) . . ?
N1A C2A N2A 121.32(19) . . ?
C3A C2A N2A 132.6(2) . . ?
C2A C3A C4A 107.94(18) . . ?
C2A C3A C12A 126.7(2) . . ?
C4A C3A C12A 125.34(19) . . ?
C5A C4A C3A 107.71(19) . . ?
C4A C5A N1A 106.99(19) . . ?
C4A C5A C13 130.9(2) . . ?
N1A C5A C13 122.02(19) . . ?
N2A C6A C8A 111.5(2) . . ?
N2A C6A C7A 113.1(2) . . ?
C8A C6A C7A 111.0(3) . . ?
N2A C9A1 C11A 112.8(3) . . ?
N2A C9A1 C10A 110.1(3) . . ?
C11A C9A1 C10A 106.2(3) . . ?
N2A C9A2 C10A 110.5(5) . . ?
N2A C9A2 C11A 109.8(5) . . ?
C10A C9A2 C11A 108.1(5) . . ?
C9A2 C10A C9A1 37.8(3) . . ?
C9A1 C11A C9A2 37.7(3) . . ?
N12A C12A C3A 177.9(3) . . ?
C5B N1B C2B 111.41(18) . . ?
C2B N2B C9B1 118.9(2) . . ?
C2B N2B C9B2 114.3(3) . . ?
C9B1 N2B C9B2 41.1(3) . . ?
C2B N2B C6B 117.2(2) . . ?
C9B1 N2B C6B 117.2(3) . . ?
C9B2 N2B C6B 126.1(3) . . ?
N1B C2B C3B 105.6(2) . . ?
N1B C2B N2B 123.3(2) . . ?
C3B C2B N2B 131.0(2) . . ?
C2B C3B C4B 108.43(19) . . ?
C2B C3B C12B 126.1(2) . . ?
C4B C3B C12B 125.5(2) . . ?
C5B C4B C3B 107.5(2) . . ?
C4B C5B N1B 107.0(2) . . ?
C4B C5B C13 130.8(2) . . ?
N1B C5B C13 122.05(19) . . ?
N2B C6B C8B2 112.7(4) . . ?
N2B C6B C7B1 117.5(4) . . ?
C8B2 C6B C7B1 74.2(5) . . ?
N2B C6B C7B2 104.2(4) . . ?
C8B2 C6B C7B2 111.8(5) . . ?
C7B1 C6B C7B2 37.8(4) . . ?
N2B C6B C8B1 110.3(3) . . ?
C8B2 C6B C8B1 34.1(4) . . ?
C7B1 C6B C8B1 104.8(5) . . ?
C7B2 C6B C8B1 139.3(4) . . ?
N2B C9B1 C11B 112.1(3) . . ?
N2B C9B1 C10B 110.6(3) . . ?
C11B C9B1 C10B 106.1(3) . . ?
N2B C9B2 C10B 110.5(5) . . ?
N2B C9B2 C11B 109.5(5) . . ?
C10B C9B2 C11B 106.8(5) . . ?
C9B2 C10B C9B1 38.6(3) . . ?
C9B1 C11B C9B2 38.1(3) . . ?
N12B C12B C3B 177.8(3) . . ?
C5B C13 C5A 111.41(19) . . ?
C5B C13 C14 108.9(2) . . ?
C5A C13 C14 109.4(2) . . ?
C5B C13 C15 109.0(2) . . ?
C5A C13 C15 108.2(2) . . ?
C14 C13 C15 109.9(2) . . ?

#===END