# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1041683'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_date             2014-08-26T14:25:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H29 Cl2 N4 Sb'
_chemical_formula_sum            'C18 H29 Cl2 N4 Sb'
_chemical_formula_weight         494.1
_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                   10.5551(6)
_cell_length_b                   12.4385(7)
_cell_length_c                   16.6000(9)
_cell_angle_alpha                87.275(4)
_cell_angle_beta                 75.794(4)
_cell_angle_gamma                86.572(4)
_cell_volume                     2107.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    48501
_cell_measurement_theta_min      5.03
_cell_measurement_theta_max      33.6
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.782
_shelx_estimated_absorpt_T_min   0.452
_shelx_estimated_absorpt_T_max   0.859

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_number            23396
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.518
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_number_total             7820
_reflns_number_gt                6561
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0250P)²+0.5724P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7820
_refine_ls_number_parameters     455
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_ref         0.0511
_refine_ls_wR_factor_gt          0.049
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5736(2) 0.75632(18) 0.04441(13) 0.0365(5) Uani 1 d . .
C2 C 0.6046(2) 0.8468(2) -0.00618(14) 0.0428(5) Uani 1 d . .
C3 C 0.5461(3) 0.8663(2) -0.07255(15) 0.0521(6) Uani 1 d . .
H3 H 0.5672 0.9262 -0.1079 0.063 Uiso 1 calc . .
C4 C 0.4571(3) 0.7966(2) -0.08554(16) 0.0545(7) Uani 1 d . .
H4 H 0.4178 0.8103 -0.1296 0.065 Uiso 1 calc . .
C5 C 0.4256(3) 0.7068(2) -0.03419(15) 0.0497(6) Uani 1 d . .
H5 H 0.3646 0.6608 -0.0433 0.06 Uiso 1 calc . .
C6 C 0.4850(2) 0.68526(19) 0.03111(14) 0.0406(5) Uani 1 d . .
C7 C 0.6937(3) 0.9247(2) 0.01498(18) 0.0520(6) Uani 1 d . .
H7A H 0.742 0.9598 -0.0358 0.062 Uiso 1 calc . .
H7B H 0.6415 0.9799 0.0495 0.062 Uiso 1 calc . .
C8 C 0.8289(2) 0.95357(19) 0.10842(17) 0.0460(6) Uani 1 d . .
H8A H 0.754 0.9786 0.1511 0.055 Uiso 1 calc . .
H8B H 0.8603 1.0148 0.0721 0.055 Uiso 1 calc . .
C9 C 0.9350(2) 0.9092(2) 0.14841(15) 0.0463(6) Uani 1 d . .
H9A H 0.9597 0.965 0.1797 0.056 Uiso 1 calc . .
H9B H 0.9024 0.8503 0.1869 0.056 Uiso 1 calc . .
C10 C 0.9053(2) 0.8273(2) -0.00151(14) 0.0435(5) Uani 1 d . .
H10A H 0.9388 0.8832 -0.0426 0.052 Uiso 1 calc . .
H10B H 0.8806 0.7688 -0.0302 0.052 Uiso 1 calc . .
C11 C 1.0108(2) 0.7867(2) 0.03999(15) 0.0476(6) Uani 1 d . .
H11A H 0.98 0.7266 0.0776 0.057 Uiso 1 calc . .
H11B H 1.0866 0.761 -0.0018 0.057 Uiso 1 calc . .
C12 C 1.1531(3) 0.8301(3) 0.12470(19) 0.0656(8) Uani 1 d . .
H12A H 1.228 0.807 0.0823 0.098 Uiso 1 calc . .
H12B H 1.1234 0.7703 0.1619 0.098 Uiso 1 calc . .
H12C H 1.1766 0.8863 0.1552 0.098 Uiso 1 calc . .
C13 C 0.4648(3) 0.58359(19) 0.08418(15) 0.0479(6) Uani 1 d . .
H13A H 0.3769 0.5608 0.0887 0.058 Uiso 1 calc . .
H13B H 0.5259 0.5273 0.0573 0.058 Uiso 1 calc . .
C14 C 0.3617(2) 0.64396(19) 0.22322(14) 0.0396(5) Uani 1 d . .
H14A H 0.2883 0.6032 0.2189 0.048 Uiso 1 calc . .
H14B H 0.3467 0.7175 0.2042 0.048 Uiso 1 calc . .
C15 C 0.3680(3) 0.64355(19) 0.31284(14) 0.0430(5) Uani 1 d . .
H15A H 0.4366 0.6892 0.3183 0.052 Uiso 1 calc . .
H15B H 0.2856 0.6726 0.3464 0.052 Uiso 1 calc . .
C16 C 0.5162(3) 0.48960(18) 0.20364(15) 0.0446(6) Uani 1 d . .
H16A H 0.6008 0.4628 0.1715 0.053 Uiso 1 calc . .
H16B H 0.4516 0.4395 0.1988 0.053 Uiso 1 calc . .
C17 C 0.5199(3) 0.49429(19) 0.29297(16) 0.0464(6) Uani 1 d . .
H17A H 0.5411 0.4229 0.3136 0.056 Uiso 1 calc . .
H17B H 0.5876 0.5413 0.2977 0.056 Uiso 1 calc . .
C18 C 0.3935(4) 0.5328(2) 0.43054(17) 0.0674(8) Uani 1 d . .
H18A H 0.4065 0.4599 0.4498 0.101 Uiso 1 calc . .
H18B H 0.311 0.5626 0.4616 0.101 Uiso 1 calc . .
H18C H 0.4627 0.575 0.4382 0.101 Uiso 1 calc . .
C19 C 0.9767(2) 0.13591(18) 0.32881(14) 0.0376(5) Uani 1 d . .
C20 C 0.9510(2) 0.04053(18) 0.37573(15) 0.0401(5) Uani 1 d . .
C21 C 1.0477(3) -0.0420(2) 0.36656(17) 0.0529(6) Uani 1 d . .
H21 H 1.0308 -0.107 0.3962 0.063 Uiso 1 calc . .
C22 C 1.1680(3) -0.0276(2) 0.31385(19) 0.0617(8) Uani 1 d . .
H22 H 1.2331 -0.0824 0.309 0.074 Uiso 1 calc . .
C23 C 1.1936(3) 0.0671(3) 0.26806(18) 0.0601(7) Uani 1 d . .
H23 H 1.2758 0.0758 0.2326 0.072 Uiso 1 calc . .
C24 C 1.0975(2) 0.1497(2) 0.27447(14) 0.0461(6) Uani 1 d . .
C25 C 0.8239(3) 0.03330(19) 0.44007(16) 0.0468(6) Uani 1 d . .
H25A H 0.7958 -0.04 0.4437 0.056 Uiso 1 calc . .
H25B H 0.8374 0.0499 0.4938 0.056 Uiso 1 calc . .
C26 C 0.6244(2) 0.1355(2) 0.50051(15) 0.0445(6) Uani 1 d . .
H26A H 0.6677 0.175 0.5341 0.053 Uiso 1 calc . .
H26B H 0.5944 0.0698 0.5312 0.053 Uiso 1 calc . .
C27 C 0.5089(3) 0.2023(2) 0.48546(17) 0.0486(6) Uani 1 d . .
H27A H 0.4496 0.2195 0.5383 0.058 Uiso 1 calc . .
H27B H 0.5383 0.2694 0.4567 0.058 Uiso 1 calc . .
C30 C 0.3259(3) 0.2084(2) 0.4235(2) 0.0669(8) Uani 1 d . .
H30A H 0.2792 0.1669 0.394 0.1 Uiso 1 calc . .
H30B H 0.3529 0.2731 0.3917 0.1 Uiso 1 calc . .
H30C H 0.2698 0.2267 0.4764 0.1 Uiso 1 calc . .
C29 C 0.5302(3) 0.1219(2) 0.35652(17) 0.0498(6) Uani 1 d . .
H29A H 0.5582 0.1889 0.3272 0.06 Uiso 1 calc . .
H29B H 0.4852 0.0839 0.323 0.06 Uiso 1 calc . .
C28 C 0.6484(2) 0.05433(19) 0.36754(16) 0.0443(6) Uani 1 d . .
H28A H 0.621 -0.0152 0.3926 0.053 Uiso 1 calc . .
H28B H 0.7072 0.0422 0.3135 0.053 Uiso 1 calc . .
C31 C 1.1154(3) 0.2530(2) 0.22221(16) 0.0570(7) Uani 1 d . .
H31A H 1.2071 0.2693 0.2085 0.068 Uiso 1 calc . .
H31B H 1.0908 0.2427 0.1706 0.068 Uiso 1 calc . .
C32 C 1.1066(2) 0.3947(2) 0.32015(16) 0.0455(6) Uani 1 d . .
H32A H 1.1926 0.414 0.2882 0.055 Uiso 1 calc . .
H32B H 1.1182 0.3425 0.3634 0.055 Uiso 1 calc . .
C33 C 1.0323(3) 0.4933(2) 0.35942(16) 0.0503(6) Uani 1 d . .
H33A H 0.9493 0.4728 0.395 0.06 Uiso 1 calc . .
H33B H 1.0817 0.5244 0.3939 0.06 Uiso 1 calc . .
C36 C 0.9338(5) 0.6661(2) 0.3386(2) 0.0883(12) Uani 1 d . .
H36A H 0.9187 0.719 0.2975 0.132 Uiso 1 calc . .
H36B H 0.9819 0.6968 0.3732 0.132 Uiso 1 calc . .
H36C H 0.8514 0.6436 0.3722 0.132 Uiso 1 calc . .
C35 C 0.9389(3) 0.5261(2) 0.24380(18) 0.0579(7) Uani 1 d . .
H35A H 0.9251 0.5792 0.2017 0.07 Uiso 1 calc . .
H35B H 0.8538 0.5055 0.2764 0.07 Uiso 1 calc . .
C34 C 1.0130(3) 0.4292(2) 0.20243(16) 0.0561(7) Uani 1 d . .
H34A H 0.9638 0.3995 0.1672 0.067 Uiso 1 calc . .
H34B H 1.0962 0.4504 0.1675 0.067 Uiso 1 calc . .
N1 N 0.78781(18) 0.87120(15) 0.05944(12) 0.0384(4) Uani 1 d . .
N2 N 1.0489(2) 0.87078(17) 0.08626(12) 0.0454(5) Uani 1 d . .
N3 N 0.48328(19) 0.59698(14) 0.16871(11) 0.0359(4) Uani 1 d . .
N4 N 0.3943(2) 0.53426(15) 0.34286(12) 0.0429(4) Uani 1 d . .
N5 N 0.71964(19) 0.10748(14) 0.42119(12) 0.0379(4) Uani 1 d . .
N6 N 0.4403(2) 0.14544(16) 0.43614(14) 0.0483(5) Uani 1 d . .
N7 N 1.0365(2) 0.34535(16) 0.26471(11) 0.0416(4) Uani 1 d . .
N8 N 1.0084(3) 0.57384(17) 0.29766(15) 0.0575(6) Uani 1 d . .
Cl1 Cl 0.51695(7) 0.88444(5) 0.21917(4) 0.05355(16) Uani 1 d . .
Cl2 Cl 0.79550(7) 0.57088(5) 0.05296(4) 0.05807(17) Uani 1 d . .
Cl3 Cl 0.90279(7) 0.27828(5) 0.48961(3) 0.04647(14) Uani 1 d . .
Cl4 Cl 0.79893(8) 0.22582(6) 0.20410(4) 0.06228(19) Uani 1 d . .
Sb1 Sb 0.66576(2) 0.72373(2) 0.14318(2) 0.03298(5) Uani 1 d . .
Sb2 Sb 0.83513(2) 0.26456(2) 0.34825(2) 0.03275(5) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.377(3) . ?
C1 C6 1.387(3) . ?
C1 Sb1 2.115(2) . ?
C2 C3 1.394(3) . ?
C2 C7 1.501(3) . ?
C3 C4 1.377(4) . ?
C3 H3 0.93 . ?
C4 C5 1.378(4) . ?
C4 H4 0.93 . ?
C5 C6 1.388(3) . ?
C5 H5 0.93 . ?
C6 C13 1.502(3) . ?
C7 N1 1.486(3) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 N1 1.485(3) . ?
C8 C9 1.501(4) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N2 1.452(3) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 N1 1.489(3) . ?
C10 C11 1.498(4) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N2 1.457(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 N2 1.456(3) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 N3 1.482(3) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 N3 1.483(3) . ?
C14 C15 1.505(3) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 N4 1.460(3) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 N3 1.487(3) . ?
C16 C17 1.497(3) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 N4 1.453(3) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 N4 1.453(3) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 C24 1.384(3) . ?
C19 C20 1.391(3) . ?
C19 Sb2 2.103(2) . ?
C20 C21 1.390(4) . ?
C20 C25 1.500(3) . ?
C21 C22 1.370(4) . ?
C21 H21 0.93 . ?
C22 C23 1.375(4) . ?
C22 H22 0.93 . ?
C23 C24 1.389(4) . ?
C23 H23 0.93 . ?
C24 C31 1.510(4) . ?
C25 N5 1.477(3) . ?
C25 H25A 0.97 . ?
C25 H25B 0.97 . ?
C26 N5 1.489(3) . ?
C26 C27 1.499(4) . ?
C26 H26A 0.97 . ?
C26 H26B 0.97 . ?
C27 N6 1.450(3) . ?
C27 H27A 0.97 . ?
C27 H27B 0.97 . ?
C30 N6 1.453(4) . ?
C30 H30A 0.96 . ?
C30 H30B 0.96 . ?
C30 H30C 0.96 . ?
C29 N6 1.456(3) . ?
C29 C28 1.506(4) . ?
C29 H29A 0.97 . ?
C29 H29B 0.97 . ?
C28 N5 1.497(3) . ?
C28 H28A 0.97 . ?
C28 H28B 0.97 . ?
C31 N7 1.478(3) . ?
C31 H31A 0.97 . ?
C31 H31B 0.97 . ?
C32 N7 1.487(3) . ?
C32 C33 1.501(4) . ?
C32 H32A 0.97 . ?
C32 H32B 0.97 . ?
C33 N8 1.455(3) . ?
C33 H33A 0.97 . ?
C33 H33B 0.97 . ?
C36 N8 1.450(4) . ?
C36 H36A 0.96 . ?
C36 H36B 0.96 . ?
C36 H36C 0.96 . ?
C35 N8 1.454(3) . ?
C35 C34 1.496(4) . ?
C35 H35A 0.97 . ?
C35 H35B 0.97 . ?
C34 N7 1.487(3) . ?
C34 H34A 0.97 . ?
C34 H34B 0.97 . ?
N1 Sb1 2.4735(18) . ?
N3 Sb1 2.5048(18) . ?
N5 Sb2 2.4708(18) . ?
N7 Sb2 2.4753(19) . ?
Cl1 Sb1 2.6356(6) . ?
Cl2 Sb1 2.5856(6) . ?
Cl3 Sb2 2.6308(6) . ?
Cl4 Sb2 2.5854(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.5(2) . . ?
C2 C1 Sb1 119.22(17) . . ?
C6 C1 Sb1 119.31(17) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 C7 118.9(2) . . ?
C3 C2 C7 122.0(2) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 C13 118.4(2) . . ?
C5 C6 C13 122.5(2) . . ?
N1 C7 C2 112.3(2) . . ?
N1 C7 H7A 109.1 . . ?
C2 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C2 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C9 111.57(19) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108 . . ?
N2 C9 C8 110.9(2) . . ?
N2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108 . . ?
N1 C10 C11 111.72(19) . . ?
N1 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C10 111.5(2) . . ?
N2 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C6 112.70(17) . . ?
N3 C13 H13A 109.1 . . ?
C6 C13 H13A 109.1 . . ?
N3 C13 H13B 109.1 . . ?
C6 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
N3 C14 C15 112.31(19) . . ?
N3 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
N4 C15 C14 110.63(18) . . ?
N4 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N3 C16 C17 111.98(18) . . ?
N3 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N3 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N4 C17 C16 110.6(2) . . ?
N4 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 120.8(2) . . ?
C24 C19 Sb2 119.84(18) . . ?
C20 C19 Sb2 119.20(17) . . ?
C21 C20 C19 119.2(2) . . ?
C21 C20 C25 121.7(2) . . ?
C19 C20 C25 118.9(2) . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120 . . ?
C20 C21 H21 120 . . ?
C21 C22 C23 120.7(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 120.4(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 118.9(2) . . ?
C19 C24 C31 117.6(2) . . ?
C23 C24 C31 123.4(2) . . ?
N5 C25 C20 112.66(19) . . ?
N5 C25 H25A 109.1 . . ?
C20 C25 H25A 109.1 . . ?
N5 C25 H25B 109.1 . . ?
C20 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
N5 C26 C27 111.7(2) . . ?
N5 C26 H26A 109.3 . . ?
C27 C26 H26A 109.3 . . ?
N5 C26 H26B 109.3 . . ?
C27 C26 H26B 109.3 . . ?
H26A C26 H26B 107.9 . . ?
N6 C27 C26 111.1(2) . . ?
N6 C27 H27A 109.4 . . ?
C26 C27 H27A 109.4 . . ?
N6 C27 H27B 109.4 . . ?
C26 C27 H27B 109.4 . . ?
H27A C27 H27B 108 . . ?
N6 C30 H30A 109.5 . . ?
N6 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N6 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N6 C29 C28 111.6(2) . . ?
N6 C29 H29A 109.3 . . ?
C28 C29 H29A 109.3 . . ?
N6 C29 H29B 109.3 . . ?
C28 C29 H29B 109.3 . . ?
H29A C29 H29B 108 . . ?
N5 C28 C29 111.72(18) . . ?
N5 C28 H28A 109.3 . . ?
C29 C28 H28A 109.3 . . ?
N5 C28 H28B 109.3 . . ?
C29 C28 H28B 109.3 . . ?
H28A C28 H28B 107.9 . . ?
N7 C31 C24 112.7(2) . . ?
N7 C31 H31A 109.1 . . ?
C24 C31 H31A 109.1 . . ?
N7 C31 H31B 109.1 . . ?
C24 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
N7 C32 C33 111.4(2) . . ?
N7 C32 H32A 109.4 . . ?
C33 C32 H32A 109.4 . . ?
N7 C32 H32B 109.4 . . ?
C33 C32 H32B 109.4 . . ?
H32A C32 H32B 108 . . ?
N8 C33 C32 112.1(2) . . ?
N8 C33 H33A 109.2 . . ?
C32 C33 H33A 109.2 . . ?
N8 C33 H33B 109.2 . . ?
C32 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
N8 C36 H36A 109.5 . . ?
N8 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N8 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N8 C35 C34 111.7(3) . . ?
N8 C35 H35A 109.3 . . ?
C34 C35 H35A 109.3 . . ?
N8 C35 H35B 109.3 . . ?
C34 C35 H35B 109.3 . . ?
H35A C35 H35B 108 . . ?
N7 C34 C35 111.3(2) . . ?
N7 C34 H34A 109.4 . . ?
C35 C34 H34A 109.4 . . ?
N7 C34 H34B 109.4 . . ?
C35 C34 H34B 109.4 . . ?
H34A C34 H34B 108 . . ?
C8 N1 C7 107.94(19) . . ?
C8 N1 C10 108.82(18) . . ?
C7 N1 C10 110.03(19) . . ?
C8 N1 Sb1 114.92(14) . . ?
C7 N1 Sb1 104.29(13) . . ?
C10 N1 Sb1 110.68(14) . . ?
C9 N2 C12 111.0(2) . . ?
C9 N2 C11 109.02(19) . . ?
C12 N2 C11 110.5(2) . . ?
C13 N3 C14 110.18(19) . . ?
C13 N3 C16 108.80(17) . . ?
C14 N3 C16 109.45(18) . . ?
C13 N3 Sb1 102.86(13) . . ?
C14 N3 Sb1 111.66(12) . . ?
C16 N3 Sb1 113.67(14) . . ?
C18 N4 C17 111.3(2) . . ?
C18 N4 C15 110.74(19) . . ?
C17 N4 C15 108.20(19) . . ?
C25 N5 C26 108.86(19) . . ?
C25 N5 C28 110.32(18) . . ?
C26 N5 C28 108.36(18) . . ?
C25 N5 Sb2 104.78(13) . . ?
C26 N5 Sb2 112.97(13) . . ?
C28 N5 Sb2 111.48(14) . . ?
C27 N6 C30 111.3(2) . . ?
C27 N6 C29 108.65(19) . . ?
C30 N6 C29 110.4(2) . . ?
C31 N7 C34 110.0(2) . . ?
C31 N7 C32 110.5(2) . . ?
C34 N7 C32 108.08(18) . . ?
C31 N7 Sb2 104.04(14) . . ?
C34 N7 Sb2 114.02(16) . . ?
C32 N7 Sb2 110.12(14) . . ?
C36 N8 C35 110.9(3) . . ?
C36 N8 C33 109.9(2) . . ?
C35 N8 C33 109.31(19) . . ?
C1 Sb1 N1 75.19(8) . . ?
C1 Sb1 N3 74.79(8) . . ?
N1 Sb1 N3 149.96(6) . . ?
C1 Sb1 Cl2 85.58(6) . . ?
N1 Sb1 Cl2 95.24(5) . . ?
N3 Sb1 Cl2 83.45(4) . . ?
C1 Sb1 Cl1 86.75(6) . . ?
N1 Sb1 Cl1 83.09(5) . . ?
N3 Sb1 Cl1 94.24(4) . . ?
Cl2 Sb1 Cl1 172.32(2) . . ?
C19 Sb2 N5 75.12(8) . . ?
C19 Sb2 N7 75.37(8) . . ?
N5 Sb2 N7 150.48(7) . . ?
C19 Sb2 Cl4 86.75(6) . . ?
N5 Sb2 Cl4 95.51(5) . . ?
N7 Sb2 Cl4 83.39(5) . . ?
C19 Sb2 Cl3 83.70(6) . . ?
N5 Sb2 Cl3 82.55(4) . . ?
N7 Sb2 Cl3 93.68(5) . . ?
Cl4 Sb2 Cl3 170.45(3) . . ?

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 -0.6(3) . . . . ?
Sb1 C1 C2 C3 178.29(18) . . . . ?
C6 C1 C2 C7 175.7(2) . . . . ?
Sb1 C1 C2 C7 -5.5(3) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C7 C2 C3 C4 -174.9(2) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
Sb1 C1 C6 C5 -179.56(17) . . . . ?
C2 C1 C6 C13 174.8(2) . . . . ?
Sb1 C1 C6 C13 -4.0(3) . . . . ?
C4 C5 C6 C1 1.3(4) . . . . ?
C4 C5 C6 C13 -174.0(2) . . . . ?
C1 C2 C7 N1 29.2(3) . . . . ?
C3 C2 C7 N1 -154.6(2) . . . . ?
N1 C8 C9 N2 58.9(3) . . . . ?
N1 C10 C11 N2 -57.2(3) . . . . ?
C1 C6 C13 N3 31.0(3) . . . . ?
C5 C6 C13 N3 -153.7(2) . . . . ?
N3 C14 C15 N4 -57.2(3) . . . . ?
N3 C16 C17 N4 58.9(3) . . . . ?
C24 C19 C20 C21 -1.0(3) . . . . ?
Sb2 C19 C20 C21 -176.02(17) . . . . ?
C24 C19 C20 C25 173.8(2) . . . . ?
Sb2 C19 C20 C25 -1.2(3) . . . . ?
C19 C20 C21 C22 2.1(4) . . . . ?
C25 C20 C21 C22 -172.5(2) . . . . ?
C20 C21 C22 C23 -1.6(4) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C20 C19 C24 C23 -0.7(3) . . . . ?
Sb2 C19 C24 C23 174.34(18) . . . . ?
C20 C19 C24 C31 176.6(2) . . . . ?
Sb2 C19 C24 C31 -8.4(3) . . . . ?
C22 C23 C24 C19 1.2(4) . . . . ?
C22 C23 C24 C31 -175.9(3) . . . . ?
C21 C20 C25 N5 -159.8(2) . . . . ?
C19 C20 C25 N5 25.6(3) . . . . ?
N5 C26 C27 N6 59.6(3) . . . . ?
N6 C29 C28 N5 -57.2(3) . . . . ?
C19 C24 C31 N7 31.6(3) . . . . ?
C23 C24 C31 N7 -151.2(2) . . . . ?
N7 C32 C33 N8 -57.4(3) . . . . ?
N8 C35 C34 N7 59.0(3) . . . . ?
C9 C8 N1 C7 -174.0(2) . . . . ?
C9 C8 N1 C10 -54.6(3) . . . . ?
C9 C8 N1 Sb1 70.1(2) . . . . ?
C2 C7 N1 C8 -155.8(2) . . . . ?
C2 C7 N1 C10 85.6(2) . . . . ?
C2 C7 N1 Sb1 -33.2(2) . . . . ?
C11 C10 N1 C8 53.7(3) . . . . ?
C11 C10 N1 C7 171.8(2) . . . . ?
C11 C10 N1 Sb1 -73.4(2) . . . . ?
C8 C9 N2 C12 178.6(2) . . . . ?
C8 C9 N2 C11 -59.4(3) . . . . ?
C10 C11 N2 C9 58.8(3) . . . . ?
C10 C11 N2 C12 -178.9(2) . . . . ?
C6 C13 N3 C14 83.2(2) . . . . ?
C6 C13 N3 C16 -156.8(2) . . . . ?
C6 C13 N3 Sb1 -36.0(2) . . . . ?
C15 C14 N3 C13 171.23(18) . . . . ?
C15 C14 N3 C16 51.6(2) . . . . ?
C15 C14 N3 Sb1 -75.12(19) . . . . ?
C17 C16 N3 C13 -172.8(2) . . . . ?
C17 C16 N3 C14 -52.4(3) . . . . ?
C17 C16 N3 Sb1 73.2(2) . . . . ?
C16 C17 N4 C18 176.3(2) . . . . ?
C16 C17 N4 C15 -61.8(2) . . . . ?
C14 C15 N4 C18 -176.9(2) . . . . ?
C14 C15 N4 C17 60.8(3) . . . . ?
C20 C25 N5 C26 -152.97(19) . . . . ?
C20 C25 N5 C28 88.2(2) . . . . ?
C20 C25 N5 Sb2 -31.9(2) . . . . ?
C27 C26 N5 C25 -174.53(18) . . . . ?
C27 C26 N5 C28 -54.5(2) . . . . ?
C27 C26 N5 Sb2 69.52(19) . . . . ?
C29 C28 N5 C25 172.4(2) . . . . ?
C29 C28 N5 C26 53.3(3) . . . . ?
C29 C28 N5 Sb2 -71.7(2) . . . . ?
C26 C27 N6 C30 178.2(2) . . . . ?
C26 C27 N6 C29 -60.0(3) . . . . ?
C28 C29 N6 C27 59.0(3) . . . . ?
C28 C29 N6 C30 -178.6(2) . . . . ?
C24 C31 N7 C34 -156.5(2) . . . . ?
C24 C31 N7 C32 84.2(3) . . . . ?
C24 C31 N7 Sb2 -33.9(2) . . . . ?
C35 C34 N7 C31 -177.2(2) . . . . ?
C35 C34 N7 C32 -56.5(3) . . . . ?
C35 C34 N7 Sb2 66.3(2) . . . . ?
C33 C32 N7 C31 176.1(2) . . . . ?
C33 C32 N7 C34 55.6(3) . . . . ?
C33 C32 N7 Sb2 -69.5(2) . . . . ?
C34 C35 N8 C36 -178.7(2) . . . . ?
C34 C35 N8 C33 -57.4(3) . . . . ?
C32 C33 N8 C36 178.6(3) . . . . ?
C32 C33 N8 C35 56.7(3) . . . . ?

_shelxl_version_number           2013-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1041684'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_date             2014-08-20T21:50:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C36  H58  N8  O2  Sb2'
_chemical_formula_sum            'C36 H58 N8 O2 Sb2'
_chemical_formula_weight         878.4

#----------------------------------------------------------------------------#
#                   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                   9.080(2)
_cell_length_b                   10.126(3)
_cell_length_c                   11.752(3)
_cell_angle_alpha                68.806(4)
_cell_angle_beta                 82.572(4)
_cell_angle_gamma                83.749(4)
_cell_volume                     996.7(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.396
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.648
_shelx_estimated_absorpt_T_max   0.758

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

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_number            9896
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.867
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_number_total             3680
_reflns_number_gt                3207
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+0.3216P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3680
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.815
_refine_diff_density_min         -1.132
_refine_diff_density_rms         0.118

#----------------------------------------------------------------------------#
#                   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'
Sb Sb -0.5866 1.5461 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5703(6) 0.5046(6) 0.7562(5) 0.0353(13) Uani 1 d . .
C2 C 0.6306(7) 0.6281(6) 0.6708(5) 0.0411(14) Uani 1 d . .
C3 C 0.7412(8) 0.6165(8) 0.5794(6) 0.0603(19) Uani 1 d . .
H3 H 0.7859 0.6973 0.5258 0.072 Uiso 1 calc . .
C4 C 0.7844(8) 0.4875(9) 0.5678(6) 0.0603(19) Uani 1 d . .
H4 H 0.8557 0.4818 0.5051 0.072 Uiso 1 calc . .
C5 C 0.7230(7) 0.3678(8) 0.6480(6) 0.0517(17) Uani 1 d . .
H5 H 0.7525 0.2806 0.6397 0.062 Uiso 1 calc . .
C6 C 0.6168(7) 0.3748(6) 0.7420(5) 0.0416(14) Uani 1 d . .
C7 C 0.5744(8) 0.7680(6) 0.6798(6) 0.0507(17) Uani 1 d . .
H7A H 0.6159 0.7806 0.7469 0.061 Uiso 1 calc . .
H7B H 0.6058 0.8435 0.6046 0.061 Uiso 1 calc . .
C8 C 0.3432(8) 0.7780(7) 0.5936(6) 0.0544(18) Uani 1 d . .
H8A H 0.3787 0.6941 0.5741 0.065 Uiso 1 calc . .
H8B H 0.372 0.8607 0.5235 0.065 Uiso 1 calc . .
C9 C 0.1773(8) 0.7825(7) 0.6173(6) 0.0579(18) Uani 1 d . .
H9A H 0.1348 0.7845 0.545 0.07 Uiso 1 calc . .
H9B H 0.1483 0.6973 0.6845 0.07 Uiso 1 calc . .
C10 C 0.3538(9) 0.8970(6) 0.7340(6) 0.0556(19) Uani 1 d . .
H10A H 0.3831 0.9837 0.6687 0.067 Uiso 1 calc . .
H10B H 0.3951 0.8921 0.8076 0.067 Uiso 1 calc . .
C11 C 0.1887(9) 0.8999(7) 0.7560(6) 0.060(2) Uani 1 d . .
H11A H 0.1602 0.8153 0.8241 0.072 Uiso 1 calc . .
H11B H 0.1521 0.9816 0.7786 0.072 Uiso 1 calc . .
C12 C -0.0418(10) 0.9129(10) 0.6676(8) 0.088(3) Uani 1 d . .
H12A H -0.0777 0.9971 0.6847 0.132 Uiso 1 calc . .
H12B H -0.0724 0.8308 0.7358 0.132 Uiso 1 calc . .
H12C H -0.082 0.9144 0.5954 0.132 Uiso 1 calc . .
C13 C 0.5491(7) 0.2424(6) 0.8298(6) 0.0445(15) Uani 1 d . .
H13A H 0.5664 0.1685 0.7944 0.053 Uiso 1 calc . .
H13B H 0.5973 0.2098 0.9051 0.053 Uiso 1 calc . .
C14 C 0.3104(7) 0.2857(7) 0.7518(5) 0.0422(14) Uani 1 d . .
H14A H 0.3306 0.2025 0.7282 0.051 Uiso 1 calc . .
H14B H 0.3459 0.3667 0.6831 0.051 Uiso 1 calc . .
C15 C 0.1439(7) 0.3090(7) 0.7794(6) 0.0538(17) Uani 1 d . .
H15A H 0.1222 0.3966 0.796 0.065 Uiso 1 calc . .
H15B H 0.0939 0.3174 0.7087 0.065 Uiso 1 calc . .
C16 C 0.3324(8) 0.1510(6) 0.9636(5) 0.0460(16) Uani 1 d . .
H16A H 0.3822 0.142 1.0345 0.055 Uiso 1 calc . .
H16B H 0.3516 0.0624 0.9483 0.055 Uiso 1 calc . .
C17 C 0.1691(7) 0.1773(7) 0.9899(6) 0.0502(16) Uani 1 d . .
H17A H 0.1324 0.0994 1.0611 0.06 Uiso 1 calc . .
H17B H 0.1502 0.2637 1.0087 0.06 Uiso 1 calc . .
C18 C -0.0692(9) 0.2080(9) 0.9100(7) 0.074(2) Uani 1 d . .
H18A H -0.095 0.297 0.9218 0.111 Uiso 1 calc . .
H18B H -0.1019 0.1319 0.9828 0.111 Uiso 1 calc . .
H18C H -0.1168 0.2068 0.8421 0.111 Uiso 1 calc . .
N1 N 0.4127(6) 0.7755(5) 0.7004(4) 0.0411(12) Uani 1 d . .
N2 N 0.1184(7) 0.9072(7) 0.6476(5) 0.0636(16) Uani 1 d . .
N3 N 0.3922(6) 0.2659(5) 0.8575(4) 0.0390(11) Uani 1 d . .
N4 N 0.0892(6) 0.1907(6) 0.8851(5) 0.0487(13) Uani 1 d . .
O1 O 0.5055(4) 0.6358(4) 0.9610(3) 0.0392(9) Uani 1 d . .
Sb1 Sb 0.39894(4) 0.51398(4) 0.90011(3) 0.03461(16) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 C6 1.397(8) . ?
C1 C2 1.404(8) . ?
C1 Sb1 2.167(6) . ?
C2 C3 1.401(9) . ?
C2 C7 1.488(8) . ?
C3 C4 1.372(10) . ?
C3 H3 0.93 . ?
C4 C5 1.362(10) . ?
C4 H4 0.93 . ?
C5 C6 1.386(8) . ?
C5 H5 0.93 . ?
C6 C13 1.502(8) . ?
C7 N1 1.456(8) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 N1 1.466(8) . ?
C8 C9 1.494(10) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N2 1.462(8) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 N1 1.453(8) . ?
C10 C11 1.487(10) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N2 1.471(9) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 N2 1.441(10) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 N3 1.434(8) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 N3 1.470(7) . ?
C14 C15 1.515(9) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 N4 1.456(8) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 N3 1.455(7) . ?
C16 C17 1.490(9) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 N4 1.467(8) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 N4 1.435(9) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
O1 Sb1 2.002(4) 2_667 ?
O1 Sb1 2.011(4) . ?
Sb1 O1 2.002(4) 2_667 ?
Sb1 Sb1 3.0789(10) 2_667 ?

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 C1 C2 118.3(5) . . ?
C6 C1 Sb1 120.1(4) . . ?
C2 C1 Sb1 121.4(4) . . ?
C3 C2 C1 119.2(6) . . ?
C3 C2 C7 121.9(6) . . ?
C1 C2 C7 118.9(5) . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.1(6) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.5(6) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.8(6) . . ?
C5 C6 C13 120.2(6) . . ?
C1 C6 C13 119.0(5) . . ?
N1 C7 C2 110.0(5) . . ?
N1 C7 H7A 109.7 . . ?
C2 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
C2 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N1 C8 C9 111.4(5) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108 . . ?
N2 C9 C8 111.4(6) . . ?
N2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
N1 C10 C11 110.7(5) . . ?
N1 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C10 112.4(6) . . ?
N2 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C6 111.8(5) . . ?
N3 C13 H13A 109.3 . . ?
C6 C13 H13A 109.3 . . ?
N3 C13 H13B 109.3 . . ?
C6 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
N3 C14 C15 112.3(5) . . ?
N3 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
N4 C15 C14 110.1(5) . . ?
N4 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N4 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
N3 C16 C17 111.2(5) . . ?
N3 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N3 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108 . . ?
N4 C17 C16 111.2(5) . . ?
N4 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
N4 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 N1 C7 112.2(5) . . ?
C10 N1 C8 109.5(5) . . ?
C7 N1 C8 112.1(5) . . ?
C12 N2 C9 111.2(7) . . ?
C12 N2 C11 112.7(6) . . ?
C9 N2 C11 106.9(5) . . ?
C13 N3 C16 112.2(5) . . ?
C13 N3 C14 111.3(5) . . ?
C16 N3 C14 109.5(5) . . ?
C18 N4 C15 111.0(5) . . ?
C18 N4 C17 112.6(5) . . ?
C15 N4 C17 108.8(5) . . ?
Sb1 O1 Sb1 100.20(16) 2_667 . ?
O1 Sb1 O1 79.80(16) 2_667 . ?
O1 Sb1 C1 96.93(18) 2_667 . ?
O1 Sb1 C1 96.18(19) . . ?
O1 Sb1 Sb1 40.01(10) 2_667 2_667 ?
O1 Sb1 Sb1 39.79(10) . 2_667 ?
C1 Sb1 Sb1 98.56(14) . 2_667 ?

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 -3.8(8) . . . . ?
Sb1 C1 C2 C3 -180.0(5) . . . . ?
C6 C1 C2 C7 175.9(5) . . . . ?
Sb1 C1 C2 C7 -0.3(7) . . . . ?
C1 C2 C3 C4 4.0(10) . . . . ?
C7 C2 C3 C4 -175.7(6) . . . . ?
C2 C3 C4 C5 -2.0(11) . . . . ?
C3 C4 C5 C6 -0.1(10) . . . . ?
C4 C5 C6 C1 0.2(10) . . . . ?
C4 C5 C6 C13 179.7(6) . . . . ?
C2 C1 C6 C5 1.8(9) . . . . ?
Sb1 C1 C6 C5 178.0(4) . . . . ?
C2 C1 C6 C13 -177.7(5) . . . . ?
Sb1 C1 C6 C13 -1.5(7) . . . . ?
C3 C2 C7 N1 135.1(6) . . . . ?
C1 C2 C7 N1 -44.6(7) . . . . ?
N1 C8 C9 N2 58.8(7) . . . . ?
N1 C10 C11 N2 -59.1(7) . . . . ?
C5 C6 C13 N3 -138.9(6) . . . . ?
C1 C6 C13 N3 40.6(7) . . . . ?
N3 C14 C15 N4 -56.8(7) . . . . ?
N3 C16 C17 N4 59.4(7) . . . . ?
C11 C10 N1 C7 -179.2(5) . . . . ?
C11 C10 N1 C8 55.6(7) . . . . ?
C2 C7 N1 C10 168.5(5) . . . . ?
C2 C7 N1 C8 -67.7(6) . . . . ?
C9 C8 N1 C10 -56.0(7) . . . . ?
C9 C8 N1 C7 178.8(5) . . . . ?
C8 C9 N2 C12 178.7(6) . . . . ?
C8 C9 N2 C11 -58.0(8) . . . . ?
C10 C11 N2 C12 -178.9(6) . . . . ?
C10 C11 N2 C9 58.7(8) . . . . ?
C6 C13 N3 C16 -165.9(5) . . . . ?
C6 C13 N3 C14 71.1(6) . . . . ?
C17 C16 N3 C13 -179.6(5) . . . . ?
C17 C16 N3 C14 -55.5(6) . . . . ?
C15 C14 N3 C13 179.3(5) . . . . ?
C15 C14 N3 C16 54.8(7) . . . . ?
C14 C15 N4 C18 -177.8(6) . . . . ?
C14 C15 N4 C17 57.7(7) . . . . ?
C16 C17 N4 C18 176.7(6) . . . . ?
C16 C17 N4 C15 -59.8(7) . . . . ?

_shelxl_version_number           2013-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1041685'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_date             2014-08-25T10:46:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C36 H58 Bi2 N8 O2, 4(H2 O)'
_chemical_formula_sum            'C36 H66 Bi2 N8 O6'
_chemical_formula_weight         1124.92

#----------------------------------------------------------------------------#
#                   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                   11.146(6)
_cell_length_b                   12.870(6)
_cell_length_c                   16.347(8)
_cell_angle_alpha                107.146(8)
_cell_angle_beta                 99.329(9)
_cell_angle_gamma                92.409(9)
_cell_volume                     2201.1(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4062
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      21.78
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    8.033
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.283
_shelx_estimated_absorpt_T_max   0.326

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_number            21104
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.326
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_reflns_number_total             8093
_reflns_number_gt                5300
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.00084(19)
_refine_ls_number_reflns         8093
_refine_ls_number_parameters     498
_refine_ls_number_restraints     12
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.733
_refine_diff_density_min         -1.322
_refine_diff_density_rms         0.217

#----------------------------------------------------------------------------#
#                   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'
Bi Bi -4.1077 10.2566 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3247(10) 0.6952(9) 0.2364(6) 0.040(3) Uani 1 d . .
C2 C 0.4320(11) 0.7183(9) 0.2092(7) 0.046(3) Uani 1 d . .
C3 C 0.4240(13) 0.7610(10) 0.1386(8) 0.063(4) Uani 1 d . .
H3 H 0.4943 0.777 0.1191 0.075 Uiso 1 calc . .
C4 C 0.3107(15) 0.7790(11) 0.0984(8) 0.072(4) Uani 1 d . .
H4 H 0.3049 0.8058 0.051 0.086 Uiso 1 calc . .
C5 C 0.2097(13) 0.7578(10) 0.1277(7) 0.056(3) Uani 1 d . .
H5 H 0.1347 0.7717 0.1007 0.067 Uiso 1 calc . .
C6 C 0.2135(10) 0.7159(9) 0.1966(6) 0.041(3) Uani 1 d . .
C7 C 0.5560(11) 0.7008(10) 0.2558(8) 0.056(3) Uani 1 d . .
H7A H 0.5714 0.625 0.2331 0.067 Uiso 1 calc . .
H7B H 0.6194 0.7456 0.2442 0.067 Uiso 1 calc . .
C8 C 0.5727(11) 0.8485(9) 0.3926(8) 0.050(3) Uani 1 d . .
H8A H 0.5036 0.8791 0.367 0.06 Uiso 1 calc . .
H8B H 0.6463 0.881 0.3818 0.06 Uiso 1 calc . .
C9 C 0.5772(11) 0.8777(10) 0.4886(8) 0.060(3) Uani 1 d . .
H9A H 0.5839 0.9565 0.5138 0.072 Uiso 1 calc . .
H9B H 0.5028 0.8477 0.5003 0.072 Uiso 1 calc . .
C10 C 0.6698(10) 0.6864(10) 0.3894(8) 0.055(3) Uani 1 d . .
H10A H 0.7433 0.7169 0.377 0.066 Uiso 1 calc . .
H10B H 0.6645 0.6075 0.365 0.066 Uiso 1 calc . .
C11 C 0.6759(11) 0.7171(10) 0.4861(8) 0.059(3) Uani 1 d . .
H11A H 0.6042 0.6825 0.4978 0.071 Uiso 1 calc . .
H11B H 0.7472 0.6892 0.5118 0.071 Uiso 1 calc . .
C12 C 0.6926(13) 0.8599(11) 0.6212(8) 0.084(5) Uani 1 d . .
H12A H 0.6887 0.9369 0.6463 0.126 Uiso 1 calc . .
H12B H 0.7691 0.8397 0.6454 0.126 Uiso 1 calc . .
H12C H 0.6268 0.8204 0.634 0.126 Uiso 1 calc . .
C13 C 0.1016(9) 0.6948(9) 0.2295(6) 0.039(3) Uani 1 d . .
H13A H 0.0368 0.7326 0.2072 0.047 Uiso 1 calc . .
H13B H 0.0757 0.6171 0.208 0.047 Uiso 1 calc . .
C14 C 0.1392(11) 0.8481(9) 0.3565(7) 0.049(3) Uani 1 d . .
H14A H 0.0702 0.8788 0.331 0.059 Uiso 1 calc . .
H14B H 0.2121 0.8736 0.34 0.059 Uiso 1 calc . .
C15 C 0.1525(12) 0.8868(10) 0.4550(8) 0.061(4) Uani 1 d . .
H15A H 0.224 0.8593 0.4807 0.073 Uiso 1 calc . .
H15B H 0.164 0.966 0.4758 0.073 Uiso 1 calc . .
C16 C 0.0143(10) 0.6913(10) 0.3516(8) 0.056(3) Uani 1 d . .
H16A H 0.0039 0.6121 0.3316 0.067 Uiso 1 calc . .
H16B H -0.0586 0.7179 0.3268 0.067 Uiso 1 calc . .
C17 C 0.0325(11) 0.7318(11) 0.4494(8) 0.059(4) Uani 1 d . .
H17A H -0.0374 0.705 0.4684 0.071 Uiso 1 calc . .
H17B H 0.1044 0.7034 0.4738 0.071 Uiso 1 calc . .
C18 C 0.0530(14) 0.8909(13) 0.5771(8) 0.093(5) Uani 1 d . .
H18A H 0.1078 0.8507 0.6049 0.139 Uiso 1 calc . .
H18B H -0.0269 0.8814 0.59 0.139 Uiso 1 calc . .
H18C H 0.0821 0.967 0.5981 0.139 Uiso 1 calc . .
C19 C 0.2698(9) 0.3909(8) 0.0994(6) 0.035(2) Uani 1 d . .
C20 C 0.1501(9) 0.3951(8) 0.0557(7) 0.039(3) Uani 1 d . .
C21 C 0.1334(11) 0.4131(9) -0.0228(7) 0.049(3) Uani 1 d . .
H21 H 0.055 0.4182 -0.0503 0.059 Uiso 1 calc . .
C22 C 0.2301(14) 0.4236(11) -0.0619(8) 0.067(4) Uani 1 d . .
H22 H 0.2165 0.437 -0.1154 0.08 Uiso 1 calc . .
C23 C 0.3481(13) 0.4149(10) -0.0243(8) 0.061(3) Uani 1 d . .
H23 H 0.4132 0.4205 -0.0523 0.073 Uiso 1 calc . .
C24 C 0.3669(10) 0.3972(9) 0.0592(7) 0.043(3) Uani 1 d . .
C25 C 0.0444(9) 0.3764(9) 0.0988(7) 0.044(3) Uani 1 d . .
H25A H 0.0381 0.4422 0.1452 0.053 Uiso 1 calc . .
H25B H -0.0309 0.3612 0.0564 0.053 Uiso 1 calc . .
C26 C 0.0652(10) 0.1818(8) 0.0684(6) 0.037(2) Uani 1 d . .
H26A H 0.1326 0.188 0.0388 0.044 Uiso 1 calc . .
H26B H -0.0098 0.1642 0.0256 0.044 Uiso 1 calc . .
C27 C 0.0821(9) 0.0933(9) 0.1093(7) 0.046(3) Uani 1 d . .
H27A H 0.0873 0.0252 0.0649 0.055 Uiso 1 calc . .
H27B H 0.158 0.1103 0.1511 0.055 Uiso 1 calc . .
C28 C -0.0409(10) 0.2756(9) 0.1792(7) 0.046(3) Uani 1 d . .
H28A H -0.1175 0.2625 0.1383 0.055 Uiso 1 calc . .
H28B H -0.0423 0.3433 0.225 0.055 Uiso 1 calc . .
C29 C -0.0279(10) 0.1843(10) 0.2172(7) 0.049(3) Uani 1 d . .
H29A H 0.045 0.2014 0.262 0.059 Uiso 1 calc . .
H29B H -0.0975 0.1778 0.2448 0.059 Uiso 1 calc . .
C30 C -0.0072(12) -0.0079(10) 0.1910(8) 0.066(4) Uani 1 d . .
H30A H 0.0122 -0.0715 0.1488 0.099 Uiso 1 calc . .
H30B H -0.0825 -0.0242 0.208 0.099 Uiso 1 calc . .
H30C H 0.0571 0.0133 0.2411 0.099 Uiso 1 calc . .
C31 C 0.4938(9) 0.3851(8) 0.1015(6) 0.038(3) Uani 1 d . .
H31A H 0.5444 0.365 0.0573 0.046 Uiso 1 calc . .
H31B H 0.5289 0.4547 0.1428 0.046 Uiso 1 calc . .
C32 C 0.4676(10) 0.1910(9) 0.0847(7) 0.048(3) Uani 1 d . .
H32A H 0.5267 0.178 0.0461 0.058 Uiso 1 calc . .
H32B H 0.387 0.1836 0.0493 0.058 Uiso 1 calc . .
C33 C 0.4729(10) 0.1084(9) 0.1326(8) 0.054(3) Uani 1 d . .
H33A H 0.411 0.1193 0.169 0.065 Uiso 1 calc . .
H33B H 0.4554 0.0357 0.0911 0.065 Uiso 1 calc . .
C34 C 0.6132(9) 0.3138(9) 0.2034(7) 0.047(3) Uani 1 d . .
H34A H 0.6268 0.3855 0.2465 0.056 Uiso 1 calc . .
H34B H 0.6776 0.3067 0.1693 0.056 Uiso 1 calc . .
C35 C 0.6173(10) 0.2259(10) 0.2492(8) 0.056(3) Uani 1 d . .
H35A H 0.6973 0.2326 0.2851 0.067 Uiso 1 calc . .
H35B H 0.5572 0.2369 0.2869 0.067 Uiso 1 calc . .
C36 C 0.5978(13) 0.0334(11) 0.2298(9) 0.079(4) Uani 1 d . .
H36A H 0.6791 0.0359 0.2611 0.118 Uiso 1 calc . .
H36B H 0.5759 -0.0371 0.1871 0.118 Uiso 1 calc . .
H36C H 0.5416 0.0458 0.2697 0.118 Uiso 1 calc . .
N1 N 0.5616(7) 0.7286(7) 0.3493(6) 0.043(2) Uani 1 d . .
N2 N 0.6822(8) 0.8338(8) 0.5274(6) 0.051(2) Uani 1 d . .
N3 N 0.1210(7) 0.7303(7) 0.3230(5) 0.039(2) Uani 1 d . .
N4 N 0.0472(9) 0.8500(10) 0.4814(6) 0.060(3) Uani 1 d . .
N5 N 0.0599(7) 0.2856(7) 0.1346(5) 0.036(2) Uani 1 d . .
N6 N -0.0197(8) 0.0803(8) 0.1533(6) 0.048(2) Uani 1 d . .
N7 N 0.4939(7) 0.3030(7) 0.1461(6) 0.040(2) Uani 1 d . .
N8 N 0.5929(8) 0.1170(8) 0.1868(7) 0.056(3) Uani 1 d . .
O1 O 0.4385(6) 0.4955(5) 0.2957(4) 0.0407(17) Uani 1 d . .
O2 O 0.1930(6) 0.4938(5) 0.2864(4) 0.0392(17) Uani 1 d . .
Bi1 Bi 0.33370(3) 0.62525(3) 0.34906(2) 0.03610(16) Uani 1 d . .
Bi2 Bi 0.29802(3) 0.36471(3) 0.23131(2) 0.03345(15) Uani 1 d . .
O3 O 0.5632(9) 0.4385(9) 0.4289(6) 0.077(3) Uani 1 d . .
H3A H 0.638(3) 0.445(12) 0.426(8) 0.093 Uiso 1 d . .
H3B H 0.528(8) 0.467(10) 0.393(6) 0.093 Uiso 1 d . .
O4 O 0.0772(9) 0.4251(10) 0.3997(6) 0.087(3) Uani 1 d . .
H4A H 0.102(10) 0.432(12) 0.356(4) 0.104 Uiso 1 d . .
H4B H 0.134(8) 0.453(12) 0.442(5) 0.104 Uiso 1 d . .
O5 O 0.7362(9) 0.0338(10) 0.0476(6) 0.091(3) Uani 1 d . .
H5A H 0.691(9) 0.063(12) 0.083(6) 0.11 Uiso 1 d . .
H5B H 0.802(6) 0.030(12) 0.079(6) 0.11 Uiso 1 d . .
O6 O 0.1725(10) 0.5442(11) 0.5752(9) 0.110(4) Uani 1 d . .
H6A H 0.143(13) 0.497(9) 0.595(11) 0.132 Uiso 1 d . .
H6B H 0.121(11) 0.591(9) 0.580(11) 0.132 Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 C6 1.378(14) . ?
C1 C2 1.392(15) . ?
C1 Bi1 2.267(10) . ?
C2 C3 1.409(15) . ?
C2 C7 1.526(15) . ?
C3 C4 1.387(18) . ?
C3 H3 0.93 . ?
C4 C5 1.341(18) . ?
C4 H4 0.93 . ?
C5 C6 1.381(14) . ?
C5 H5 0.93 . ?
C6 C13 1.480(14) . ?
C7 N1 1.453(13) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 N1 1.487(13) . ?
C8 C9 1.495(15) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N2 1.455(13) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 N1 1.479(13) . ?
C10 C11 1.503(15) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N2 1.447(14) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 N2 1.454(14) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 N3 1.437(11) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 N3 1.444(13) . ?
C14 C15 1.518(14) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 N4 1.424(15) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 N3 1.467(13) . ?
C16 C17 1.505(15) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 N4 1.448(15) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 N4 1.484(14) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 C24 1.365(14) . ?
C19 C20 1.419(13) . ?
C19 Bi2 2.254(10) . ?
C20 C21 1.356(14) . ?
C20 C25 1.512(15) . ?
C21 C22 1.361(16) . ?
C21 H21 0.93 . ?
C22 C23 1.382(17) . ?
C22 H22 0.93 . ?
C23 C24 1.433(14) . ?
C23 H23 0.93 . ?
C24 C31 1.506(14) . ?
C25 N5 1.458(12) . ?
C25 H25A 0.97 . ?
C25 H25B 0.97 . ?
C26 N5 1.461(12) . ?
C26 C27 1.484(14) . ?
C26 H26A 0.97 . ?
C26 H26B 0.97 . ?
C27 N6 1.468(13) . ?
C27 H27A 0.97 . ?
C27 H27B 0.97 . ?
C28 N5 1.455(12) . ?
C28 C29 1.484(15) . ?
C28 H28A 0.97 . ?
C28 H28B 0.97 . ?
C29 N6 1.451(13) . ?
C29 H29A 0.97 . ?
C29 H29B 0.97 . ?
C30 N6 1.444(13) . ?
C30 H30A 0.96 . ?
C30 H30B 0.96 . ?
C30 H30C 0.96 . ?
C31 N7 1.451(12) . ?
C31 H31A 0.97 . ?
C31 H31B 0.97 . ?
C32 N7 1.479(12) . ?
C32 C33 1.493(15) . ?
C32 H32A 0.97 . ?
C32 H32B 0.97 . ?
C33 N8 1.460(14) . ?
C33 H33A 0.97 . ?
C33 H33B 0.97 . ?
C34 N7 1.472(13) . ?
C34 C35 1.526(15) . ?
C34 H34A 0.97 . ?
C34 H34B 0.97 . ?
C35 N8 1.455(14) . ?
C35 H35A 0.97 . ?
C35 H35B 0.97 . ?
C36 N8 1.447(15) . ?
C36 H36A 0.96 . ?
C36 H36B 0.96 . ?
C36 H36C 0.96 . ?
N7 Bi2 2.796(8) . ?
O1 Bi1 2.133(6) . ?
O1 Bi2 2.143(7) . ?
O2 Bi2 2.137(6) . ?
O2 Bi1 2.146(7) . ?
Bi1 Bi2 3.3077(16) . ?
O3 H3A 0.85(5) . ?
O3 H3B 0.84(11) . ?
O4 H4A 0.83(10) . ?
O4 H4B 0.84(9) . ?
O5 H5A 0.84(11) . ?
O5 H5B 0.84(8) . ?
O6 H6A 0.85(14) . ?
O6 H6B 0.85(13) . ?

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 C1 C2 120.9(10) . . ?
C6 C1 Bi1 119.7(8) . . ?
C2 C1 Bi1 119.4(8) . . ?
C1 C2 C3 118.4(11) . . ?
C1 C2 C7 121.1(10) . . ?
C3 C2 C7 120.5(11) . . ?
C4 C3 C2 119.7(12) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.1(12) . . ?
C5 C4 H4 120 . . ?
C3 C4 H4 120 . . ?
C4 C5 C6 122.1(12) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C1 C6 C5 118.8(11) . . ?
C1 C6 C13 119.5(9) . . ?
C5 C6 C13 121.6(10) . . ?
N1 C7 C2 111.7(9) . . ?
N1 C7 H7A 109.3 . . ?
C2 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C2 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C9 112.9(9) . . ?
N1 C8 H8A 109 . . ?
C9 C8 H8A 109 . . ?
N1 C8 H8B 109 . . ?
C9 C8 H8B 109 . . ?
H8A C8 H8B 107.8 . . ?
N2 C9 C8 109.2(10) . . ?
N2 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
N2 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
N1 C10 C11 109.6(9) . . ?
N1 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N2 C11 C10 113.2(10) . . ?
N2 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
N2 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C6 111.9(8) . . ?
N3 C13 H13A 109.2 . . ?
C6 C13 H13A 109.2 . . ?
N3 C13 H13B 109.2 . . ?
C6 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N3 C14 C15 111.1(9) . . ?
N3 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N3 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108 . . ?
N4 C15 C14 110.9(11) . . ?
N4 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108 . . ?
N3 C16 C17 109.4(10) . . ?
N3 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
N3 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
N4 C17 C16 111.2(10) . . ?
N4 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
N4 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 119.6(10) . . ?
C24 C19 Bi2 120.3(8) . . ?
C20 C19 Bi2 120.0(7) . . ?
C21 C20 C19 120.0(10) . . ?
C21 C20 C25 122.3(9) . . ?
C19 C20 C25 117.7(9) . . ?
C20 C21 C22 120.7(11) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 121.8(11) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C22 C23 C24 118.0(12) . . ?
C22 C23 H23 121 . . ?
C24 C23 H23 121 . . ?
C19 C24 C23 119.8(11) . . ?
C19 C24 C31 120.7(9) . . ?
C23 C24 C31 119.5(10) . . ?
N5 C25 C20 111.6(8) . . ?
N5 C25 H25A 109.3 . . ?
C20 C25 H25A 109.3 . . ?
N5 C25 H25B 109.3 . . ?
C20 C25 H25B 109.3 . . ?
H25A C25 H25B 108 . . ?
N5 C26 C27 110.2(8) . . ?
N5 C26 H26A 109.6 . . ?
C27 C26 H26A 109.6 . . ?
N5 C26 H26B 109.6 . . ?
C27 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
N6 C27 C26 111.0(8) . . ?
N6 C27 H27A 109.4 . . ?
C26 C27 H27A 109.4 . . ?
N6 C27 H27B 109.4 . . ?
C26 C27 H27B 109.4 . . ?
H27A C27 H27B 108 . . ?
N5 C28 C29 110.6(9) . . ?
N5 C28 H28A 109.5 . . ?
C29 C28 H28A 109.5 . . ?
N5 C28 H28B 109.5 . . ?
C29 C28 H28B 109.5 . . ?
H28A C28 H28B 108.1 . . ?
N6 C29 C28 113.1(9) . . ?
N6 C29 H29A 109 . . ?
C28 C29 H29A 109 . . ?
N6 C29 H29B 109 . . ?
C28 C29 H29B 109 . . ?
H29A C29 H29B 107.8 . . ?
N6 C30 H30A 109.5 . . ?
N6 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N6 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N7 C31 C24 111.9(8) . . ?
N7 C31 H31A 109.2 . . ?
C24 C31 H31A 109.2 . . ?
N7 C31 H31B 109.2 . . ?
C24 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
N7 C32 C33 110.8(9) . . ?
N7 C32 H32A 109.5 . . ?
C33 C32 H32A 109.5 . . ?
N7 C32 H32B 109.5 . . ?
C33 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
N8 C33 C32 111.2(10) . . ?
N8 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
N8 C33 H33B 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108 . . ?
N7 C34 C35 110.4(9) . . ?
N7 C34 H34A 109.6 . . ?
C35 C34 H34A 109.6 . . ?
N7 C34 H34B 109.6 . . ?
C35 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
N8 C35 C34 111.4(10) . . ?
N8 C35 H35A 109.4 . . ?
C34 C35 H35A 109.4 . . ?
N8 C35 H35B 109.4 . . ?
C34 C35 H35B 109.4 . . ?
H35A C35 H35B 108 . . ?
N8 C36 H36A 109.5 . . ?
N8 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N8 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C7 N1 C10 110.1(9) . . ?
C7 N1 C8 112.5(9) . . ?
C10 N1 C8 106.8(9) . . ?
C11 N2 C12 111.3(10) . . ?
C11 N2 C9 109.8(9) . . ?
C12 N2 C9 112.1(10) . . ?
C13 N3 C14 110.6(8) . . ?
C13 N3 C16 109.3(9) . . ?
C14 N3 C16 109.4(8) . . ?
C15 N4 C17 108.1(9) . . ?
C15 N4 C18 112.9(11) . . ?
C17 N4 C18 111.6(11) . . ?
C28 N5 C25 108.9(8) . . ?
C28 N5 C26 109.3(8) . . ?
C25 N5 C26 113.0(8) . . ?
C30 N6 C29 112.7(9) . . ?
C30 N6 C27 111.8(9) . . ?
C29 N6 C27 108.2(9) . . ?
C31 N7 C34 109.2(8) . . ?
C31 N7 C32 112.1(8) . . ?
C34 N7 C32 110.1(8) . . ?
C31 N7 Bi2 98.5(5) . . ?
C34 N7 Bi2 115.4(6) . . ?
C32 N7 Bi2 111.1(6) . . ?
C36 N8 C35 111.6(10) . . ?
C36 N8 C33 110.4(10) . . ?
C35 N8 C33 108.8(8) . . ?
Bi1 O1 Bi2 101.4(3) . . ?
Bi2 O2 Bi1 101.1(3) . . ?
O1 Bi1 O2 78.7(2) . . ?
O1 Bi1 C1 94.8(3) . . ?
O2 Bi1 C1 96.6(3) . . ?
O1 Bi1 Bi2 39.43(18) . . ?
O2 Bi1 Bi2 39.33(17) . . ?
C1 Bi1 Bi2 96.8(3) . . ?
O2 Bi2 O1 78.7(2) . . ?
O2 Bi2 C19 94.4(3) . . ?
O1 Bi2 C19 97.5(3) . . ?
O2 Bi2 N7 147.0(2) . . ?
O1 Bi2 N7 76.2(3) . . ?
C19 Bi2 N7 68.3(3) . . ?
O2 Bi2 Bi1 39.53(18) . . ?
O1 Bi2 Bi1 39.22(17) . . ?
C19 Bi2 Bi1 97.2(2) . . ?
N7 Bi2 Bi1 112.47(18) . . ?
H3A O3 H3B 105(12) . . ?
H4A O4 H4B 106(10) . . ?
H5A O5 H5B 105(9) . . ?
H6A O6 H6B 104(14) . . ?

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 -1.5(16) . . . . ?
Bi1 C1 C2 C3 179.5(8) . . . . ?
C6 C1 C2 C7 177.0(10) . . . . ?
Bi1 C1 C2 C7 -2.0(14) . . . . ?
C1 C2 C3 C4 0.1(17) . . . . ?
C7 C2 C3 C4 -178.4(11) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C3 C4 C5 C6 -1(2) . . . . ?
C2 C1 C6 C5 1.5(16) . . . . ?
Bi1 C1 C6 C5 -179.5(8) . . . . ?
C2 C1 C6 C13 -177.4(10) . . . . ?
Bi1 C1 C6 C13 1.5(14) . . . . ?
C4 C5 C6 C1 -0.1(18) . . . . ?
C4 C5 C6 C13 178.8(11) . . . . ?
C1 C2 C7 N1 -37.1(14) . . . . ?
C3 C2 C7 N1 141.3(10) . . . . ?
N1 C8 C9 N2 59.8(13) . . . . ?
N1 C10 C11 N2 -58.5(13) . . . . ?
C1 C6 C13 N3 42.1(14) . . . . ?
C5 C6 C13 N3 -136.8(11) . . . . ?
N3 C14 C15 N4 -58.7(13) . . . . ?
N3 C16 C17 N4 60.0(12) . . . . ?
C24 C19 C20 C21 -4.7(16) . . . . ?
Bi2 C19 C20 C21 178.7(8) . . . . ?
C24 C19 C20 C25 173.9(10) . . . . ?
Bi2 C19 C20 C25 -2.7(12) . . . . ?
C19 C20 C21 C22 2.2(17) . . . . ?
C25 C20 C21 C22 -176.3(11) . . . . ?
C20 C21 C22 C23 1(2) . . . . ?
C21 C22 C23 C24 -1.6(19) . . . . ?
C20 C19 C24 C23 4.0(16) . . . . ?
Bi2 C19 C24 C23 -179.4(8) . . . . ?
C20 C19 C24 C31 -175.7(9) . . . . ?
Bi2 C19 C24 C31 0.9(14) . . . . ?
C22 C23 C24 C19 -0.9(17) . . . . ?
C22 C23 C24 C31 178.8(11) . . . . ?
C21 C20 C25 N5 135.3(10) . . . . ?
C19 C20 C25 N5 -43.2(12) . . . . ?
N5 C26 C27 N6 60.4(11) . . . . ?
N5 C28 C29 N6 -56.7(12) . . . . ?
C19 C24 C31 N7 38.2(13) . . . . ?
C23 C24 C31 N7 -141.6(10) . . . . ?
N7 C32 C33 N8 -59.1(12) . . . . ?
N7 C34 C35 N8 57.2(12) . . . . ?
C2 C7 N1 C10 166.5(9) . . . . ?
C2 C7 N1 C8 -74.5(11) . . . . ?
C11 C10 N1 C7 179.1(10) . . . . ?
C11 C10 N1 C8 56.6(12) . . . . ?
C9 C8 N1 C7 179.4(9) . . . . ?
C9 C8 N1 C10 -59.7(12) . . . . ?
C10 C11 N2 C12 -177.8(10) . . . . ?
C10 C11 N2 C9 57.5(13) . . . . ?
C8 C9 N2 C11 -56.1(13) . . . . ?
C8 C9 N2 C12 179.7(10) . . . . ?
C6 C13 N3 C14 68.7(11) . . . . ?
C6 C13 N3 C16 -170.8(9) . . . . ?
C15 C14 N3 C13 176.7(9) . . . . ?
C15 C14 N3 C16 56.3(12) . . . . ?
C17 C16 N3 C13 -178.0(9) . . . . ?
C17 C16 N3 C14 -56.8(11) . . . . ?
C14 C15 N4 C17 59.1(12) . . . . ?
C14 C15 N4 C18 -176.9(10) . . . . ?
C16 C17 N4 C15 -60.9(12) . . . . ?
C16 C17 N4 C18 174.4(10) . . . . ?
C29 C28 N5 C25 -179.6(9) . . . . ?
C29 C28 N5 C26 56.5(11) . . . . ?
C20 C25 N5 C28 176.9(8) . . . . ?
C20 C25 N5 C26 -61.4(11) . . . . ?
C27 C26 N5 C28 -59.0(11) . . . . ?
C27 C26 N5 C25 179.5(8) . . . . ?
C28 C29 N6 C30 -180.0(10) . . . . ?
C28 C29 N6 C27 55.8(12) . . . . ?
C26 C27 N6 C30 178.0(9) . . . . ?
C26 C27 N6 C29 -57.3(11) . . . . ?
C24 C31 N7 C34 -166.1(8) . . . . ?
C24 C31 N7 C32 71.6(10) . . . . ?
C24 C31 N7 Bi2 -45.3(8) . . . . ?
C35 C34 N7 C31 -178.2(8) . . . . ?
C35 C34 N7 C32 -54.7(11) . . . . ?
C35 C34 N7 Bi2 72.0(9) . . . . ?
C33 C32 N7 C31 177.9(8) . . . . ?
C33 C32 N7 C34 56.1(11) . . . . ?
C33 C32 N7 Bi2 -73.0(9) . . . . ?
C34 C35 N8 C36 179.5(9) . . . . ?
C34 C35 N8 C33 -58.5(12) . . . . ?
C32 C33 N8 C36 -177.6(9) . . . . ?
C32 C33 N8 C35 59.6(12) . . . . ?

_shelxl_version_number           2013-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1041686'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_date             2014-08-26T14:33:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C36 H61 N8 O2 Sb2, 3(C2 F3 O2), C7 H8, H2 O'
_chemical_formula_sum            'C49 H71 F9 N8 O9 Sb2'
_chemical_formula_weight         1330.63

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0460(11)
_cell_length_b                   28.780(3)
_cell_length_c                   18.4055(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.829(2)
_cell_angle_gamma                90
_cell_volume                     5820.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    3994
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      19.62
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2704
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.693
_shelx_estimated_absorpt_T_max   0.786

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

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_number            43470
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.8
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             10835
_reflns_number_gt                7744
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10835
_refine_ls_number_parameters     696
_refine_ls_number_restraints     5
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.057
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.112

#----------------------------------------------------------------------------#
#                   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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6233(5) 0.35707(19) 0.2743(3) 0.0337(14) Uani 1 d . .
C2 C 0.6747(6) 0.3634(2) 0.2087(3) 0.0403(15) Uani 1 d . .
C3 C 0.5998(7) 0.3709(2) 0.1452(3) 0.0535(19) Uani 1 d . .
H3 H 0.634 0.3744 0.1008 0.064 Uiso 1 calc . .
C4 C 0.4751(7) 0.3733(2) 0.1460(4) 0.059(2) Uani 1 d . .
H4 H 0.4251 0.3774 0.1021 0.071 Uiso 1 calc . .
C5 C 0.4245(6) 0.3698(2) 0.2098(4) 0.0485(17) Uani 1 d . .
H5 H 0.3398 0.3728 0.2101 0.058 Uiso 1 calc . .
C6 C 0.4971(6) 0.3618(2) 0.2750(3) 0.0384(15) Uani 1 d . .
C7 C 0.8104(6) 0.3618(2) 0.2088(3) 0.0464(17) Uani 1 d . .
H7A H 0.8369 0.3295 0.2053 0.056 Uiso 1 calc . .
H7B H 0.8345 0.3787 0.1664 0.056 Uiso 1 calc . .
C8 C 0.8516(6) 0.4337(2) 0.2743(4) 0.0521(18) Uani 1 d . .
H8A H 0.7643 0.4407 0.2682 0.063 Uiso 1 calc . .
H8B H 0.8886 0.4469 0.2328 0.063 Uiso 1 calc . .
C9 C 0.9095(6) 0.4548(2) 0.3450(4) 0.058(2) Uani 1 d . .
H9A H 0.8978 0.4886 0.3436 0.069 Uiso 1 calc . .
H9B H 0.8694 0.4426 0.3861 0.069 Uiso 1 calc . .
C10 C 1.0020(6) 0.3724(2) 0.2857(4) 0.0498(18) Uani 1 d . .
H10A H 1.0405 0.3849 0.2442 0.06 Uiso 1 calc . .
H10B H 1.0142 0.3386 0.2868 0.06 Uiso 1 calc . .
C11 C 1.0593(6) 0.3933(3) 0.3551(4) 0.057(2) Uani 1 d . .
H11A H 1.0237 0.3793 0.3966 0.068 Uiso 1 calc . .
H11B H 1.1467 0.3865 0.3604 0.068 Uiso 1 calc . .
C12 C 1.1001(7) 0.4659(3) 0.4235(4) 0.071(2) Uani 1 d . .
H12A H 1.1875 0.4616 0.4257 0.106 Uiso 1 calc . .
H12B H 1.07 0.4514 0.4658 0.106 Uiso 1 calc . .
H12C H 1.0815 0.4988 0.4233 0.106 Uiso 1 calc . .
C13 C 0.4421(5) 0.3585(2) 0.3470(3) 0.0375(15) Uani 1 d . .
H13A H 0.3696 0.3782 0.3454 0.045 Uiso 1 calc . .
H13B H 0.4171 0.3263 0.355 0.045 Uiso 1 calc . .
C14 C 0.5399(6) 0.42488(19) 0.4108(3) 0.0394(15) Uani 1 d . .
H14A H 0.4584 0.438 0.4122 0.047 Uiso 1 calc . .
H14B H 0.5722 0.4362 0.3665 0.047 Uiso 1 calc . .
C15 C 0.6205(6) 0.4415(2) 0.4763(3) 0.0407(16) Uani 1 d . .
H15A H 0.704 0.431 0.4728 0.049 Uiso 1 calc . .
H15B H 0.6207 0.4756 0.4773 0.049 Uiso 1 calc . .
C16 C 0.4935(5) 0.3565(2) 0.4783(3) 0.0356(14) Uani 1 d . .
H16A H 0.4927 0.3224 0.4784 0.043 Uiso 1 calc . .
H16B H 0.4108 0.3673 0.4836 0.043 Uiso 1 calc . .
C17 C 0.5776(5) 0.3734(2) 0.5417(3) 0.0377(15) Uani 1 d . .
H17A H 0.5507 0.3616 0.5873 0.045 Uiso 1 calc . .
H17B H 0.6601 0.3618 0.5376 0.045 Uiso 1 calc . .
C18 C 0.6532(6) 0.4416(2) 0.6071(3) 0.0550(19) Uani 1 d . .
H18A H 0.7366 0.4314 0.6058 0.082 Uiso 1 calc . .
H18B H 0.622 0.4298 0.6509 0.082 Uiso 1 calc . .
H18C H 0.6505 0.4753 0.6073 0.082 Uiso 1 calc . .
C19 C 0.6590(5) 0.23775(18) 0.2189(3) 0.0304(13) Uani 1 d . .
C20 C 0.5355(5) 0.2432(2) 0.1945(3) 0.0357(14) Uani 1 d . .
C21 C 0.4994(6) 0.2502(2) 0.1207(3) 0.0450(17) Uani 1 d . .
H21 H 0.4166 0.2541 0.1044 0.054 Uiso 1 calc . .
C22 C 0.5848(7) 0.2514(2) 0.0718(3) 0.0468(17) Uani 1 d . .
H22 H 0.5607 0.2576 0.0223 0.056 Uiso 1 calc . .
C23 C 0.7054(6) 0.24373(19) 0.0945(3) 0.0415(16) Uani 1 d . .
H23 H 0.7624 0.2428 0.0599 0.05 Uiso 1 calc . .
C24 C 0.7435(5) 0.23740(19) 0.1678(3) 0.0340(14) Uani 1 d . .
C25 C 0.4439(5) 0.2410(2) 0.2504(3) 0.0374(15) Uani 1 d . .
H25A H 0.4387 0.2715 0.2736 0.045 Uiso 1 calc . .
H25B H 0.3634 0.2334 0.2259 0.045 Uiso 1 calc . .
C26 C 0.4572(6) 0.1588(2) 0.2746(3) 0.0418(16) Uani 1 d . .
H26A H 0.5128 0.1536 0.2371 0.05 Uiso 1 calc . .
H26B H 0.3737 0.1573 0.2508 0.05 Uiso 1 calc . .
C27 C 0.4751(6) 0.1209(2) 0.3312(3) 0.0452(17) Uani 1 d . .
H27A H 0.4586 0.0906 0.3079 0.054 Uiso 1 calc . .
H27B H 0.5597 0.121 0.3532 0.054 Uiso 1 calc . .
C28 C 0.4038(5) 0.2114(2) 0.3683(3) 0.0395(16) Uani 1 d . .
H28A H 0.3177 0.2123 0.3492 0.047 Uiso 1 calc . .
H28B H 0.4239 0.241 0.3928 0.047 Uiso 1 calc . .
C29 C 0.4243(6) 0.1720(2) 0.4230(3) 0.0450(17) Uani 1 d . .
H29A H 0.5095 0.1719 0.4439 0.054 Uiso 1 calc . .
H29B H 0.3731 0.1767 0.4629 0.054 Uiso 1 calc . .
C30 C 0.4051(7) 0.0900(2) 0.4394(4) 0.068(2) Uani 1 d . .
H30A H 0.3915 0.0608 0.4138 0.102 Uiso 1 calc . .
H30B H 0.345 0.0938 0.4739 0.102 Uiso 1 calc . .
H30C H 0.486 0.0902 0.4655 0.102 Uiso 1 calc . .
C31 C 0.8767(6) 0.2295(2) 0.1899(3) 0.0417(16) Uani 1 d . .
H31A H 0.9158 0.2193 0.1472 0.05 Uiso 1 calc . .
H31B H 0.9144 0.259 0.2067 0.05 Uiso 1 calc . .
C32 C 0.8657(6) 0.1479(2) 0.2199(3) 0.0424(16) Uani 1 d . .
H32A H 0.9136 0.1405 0.1794 0.051 Uiso 1 calc . .
H32B H 0.7795 0.1474 0.2011 0.051 Uiso 1 calc . .
C33 C 0.8886(5) 0.1121(2) 0.2781(4) 0.0444(16) Uani 1 d . .
H33A H 0.8365 0.1182 0.3171 0.053 Uiso 1 calc . .
H33B H 0.8676 0.0813 0.2577 0.053 Uiso 1 calc . .
C34 C 1.0280(5) 0.1952(2) 0.2767(3) 0.0397(15) Uani 1 d . .
H34A H 1.0501 0.2261 0.2962 0.048 Uiso 1 calc . .
H34B H 1.0782 0.1885 0.237 0.048 Uiso 1 calc . .
C35 C 1.0527(6) 0.1592(2) 0.3365(4) 0.0443(17) Uani 1 d . .
H35A H 1.1393 0.1596 0.3544 0.053 Uiso 1 calc . .
H35B H 1.0061 0.1669 0.3775 0.053 Uiso 1 calc . .
C36 C 1.0443(6) 0.0760(2) 0.3653(4) 0.060(2) Uani 1 d . .
H36A H 1.0162 0.0461 0.3457 0.089 Uiso 1 calc . .
H36B H 1.0025 0.0834 0.4077 0.089 Uiso 1 calc . .
H36C H 1.1313 0.0746 0.3794 0.089 Uiso 1 calc . .
N1 N 0.8700(5) 0.38290(17) 0.2765(3) 0.0402(13) Uani 1 d . .
N2 N 1.0410(5) 0.4443(2) 0.3563(3) 0.0572(16) Uani 1 d . .
H2 H 1.0792 0.4576 0.3145 0.069 Uiso 1 calc . .
N3 N 0.5307(4) 0.37320(15) 0.4075(2) 0.0301(11) Uani 1 d . .
N4 N 0.5786(4) 0.42403(16) 0.5429(3) 0.0363(12) Uani 1 d . .
N5 N 0.4795(4) 0.20555(16) 0.3069(2) 0.0329(11) Uani 1 d . .
N6 N 0.3944(5) 0.12785(18) 0.3874(3) 0.0467(14) Uani 1 d . .
N7 N 0.8985(4) 0.19485(15) 0.2480(2) 0.0305(11) Uani 1 d . .
N8 N 1.0183(4) 0.11233(17) 0.3090(3) 0.0404(13) Uani 1 d . .
H8 H 1.0682 0.1054 0.2686 0.048 Uiso 1 calc . .
O1 O 0.8297(3) 0.28338(12) 0.3285(2) 0.0306(9) Uani 1 d . .
H1A H 0.894(3) 0.2783(18) 0.356(2) 0.037 Uiso 1 d . .
O2 O 0.6221(3) 0.28014(11) 0.37874(19) 0.0277(9) Uani 1 d . .
Sb1 Sb 0.72138(3) 0.33785(2) 0.37608(2) 0.02945(12) Uani 1 d . .
Sb2 Sb 0.70648(3) 0.22774(2) 0.33440(2) 0.02914(12) Uani 1 d . .
C37 C 0.1608(7) 0.2830(4) 0.5161(5) 0.085(3) Uani 1 d . .
C38 C 0.0384(6) 0.2817(2) 0.4706(4) 0.0489(18) Uani 1 d . .
F1 F 0.1618(6) 0.2796(4) 0.5838(3) 0.196(4) Uani 1 d . .
F2 F 0.2383(7) 0.2541(4) 0.4983(4) 0.220(6) Uani 1 d . .
F3 F 0.2162(8) 0.3187(4) 0.5069(7) 0.271(7) Uani 1 d . .
O3 O 0.0418(4) 0.2720(2) 0.4071(3) 0.0820(18) Uani 1 d . .
O4 O -0.0460(5) 0.2931(2) 0.5035(3) 0.0874(18) Uani 1 d . .
C39 C 0.2848(8) 0.4312(4) 0.6290(6) 0.084(3) Uani 1 d . .
C40 C 0.1712(9) 0.4189(3) 0.6742(6) 0.079(3) Uani 1 d . .
F4 F 0.2583(5) 0.4446(3) 0.5666(4) 0.201(4) Uani 1 d . .
F5 F 0.3513(8) 0.4658(3) 0.6553(4) 0.192(4) Uani 1 d . .
F6 F 0.3574(6) 0.3989(2) 0.6319(4) 0.162(3) Uani 1 d . .
O5 O 0.2013(7) 0.4084(4) 0.7297(4) 0.186(5) Uani 1 d . .
O6 O 0.0756(6) 0.4293(2) 0.6407(4) 0.108(2) Uani 1 d . .
C41 C 0.3203(7) 0.4962(3) 0.1930(5) 0.059(2) Uani 1 d . .
C42 C 0.2335(7) 0.4778(2) 0.2457(4) 0.0477(17) Uani 1 d . .
F7 F 0.4364(5) 0.4909(2) 0.2180(3) 0.119(2) Uani 1 d . .
F8 F 0.3106(5) 0.47254(19) 0.1318(3) 0.1058(18) Uani 1 d . .
F9 F 0.3076(5) 0.53979(17) 0.1778(4) 0.143(3) Uani 1 d . .
O7 O 0.1297(5) 0.49232(18) 0.2366(3) 0.0758(16) Uani 1 d . .
O8 O 0.2766(5) 0.45108(19) 0.2930(3) 0.0805(17) Uani 1 d . .
O9 O 0.9306(7) 0.3949(3) 0.5259(5) 0.119(2) Uani 1 d . .
H9C H 0.927(9) 0.3666(11) 0.514(6) 0.143 Uiso 1 d . .
H9D H 0.987(7) 0.397(3) 0.560(4) 0.143 Uiso 1 d . .
C43 C 0.8736(9) 0.4276(3) 0.0309(4) 0.123(5) Uani 1 d . .
C44 C 0.8329(7) 0.3843(5) 0.0053(3) 0.104(4) Uani 1 d . .
H44 H 0.7543 0.3811 -0.0191 0.125 Uiso 1 calc . .
C45 C 0.9084(13) 0.3457(3) 0.0157(4) 0.127(5) Uani 1 d . .
H45 H 0.8808 0.3164 -0.0016 0.153 Uiso 1 calc . .
C46 C 1.0245(11) 0.3504(4) 0.0517(5) 0.191(9) Uani 1 d . .
H46 H 1.0756 0.3243 0.0588 0.229 Uiso 1 calc . .
C47 C 1.0652(6) 0.3937(5) 0.0774(3) 0.144(5) Uani 1 d . .
H47 H 1.1438 0.3968 0.1017 0.173 Uiso 1 calc . .
C48 C 0.9897(11) 0.4323(3) 0.0669(4) 0.096(4) Uani 1 d . .
H48 H 1.0173 0.4615 0.0842 0.116 Uiso 1 calc . .
C49 C 0.8062(15) 0.4648(5) 0.0283(8) 0.236(9) Uani 1 d . .
H49A H 0.727 0.458 0.0029 0.283 Uiso 1 calc . .
H49B H 0.8451 0.4892 0.0025 0.283 Uiso 1 calc . .
H49C H 0.7966 0.4751 0.0775 0.283 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.398(8) . ?
C1 C6 1.402(8) . ?
C1 Sb1 2.140(6) . ?
C2 C3 1.378(9) . ?
C2 C7 1.499(8) . ?
C3 C4 1.380(9) . ?
C3 H3 0.94 . ?
C4 C5 1.355(9) . ?
C4 H4 0.94 . ?
C5 C6 1.392(8) . ?
C5 H5 0.94 . ?
C6 C13 1.517(8) . ?
C7 N1 1.479(7) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C8 N1 1.475(7) . ?
C8 C9 1.518(9) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C9 N2 1.479(8) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C10 N1 1.482(7) . ?
C10 C11 1.495(9) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C11 N2 1.481(8) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C12 N2 1.477(8) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C12 H12C 0.97 . ?
C13 N3 1.468(7) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C14 N3 1.492(7) . ?
C14 C15 1.501(8) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C15 N4 1.444(7) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C16 N3 1.485(7) . ?
C16 C17 1.498(8) . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C17 N4 1.457(7) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C18 N4 1.461(7) . ?
C18 H18A 0.97 . ?
C18 H18B 0.97 . ?
C18 H18C 0.97 . ?
C19 C24 1.391(8) . ?
C19 C20 1.401(8) . ?
C19 Sb2 2.156(6) . ?
C20 C21 1.392(8) . ?
C20 C25 1.515(8) . ?
C21 C22 1.368(8) . ?
C21 H21 0.94 . ?
C22 C23 1.372(8) . ?
C22 H22 0.94 . ?
C23 C24 1.385(8) . ?
C23 H23 0.94 . ?
C24 C31 1.504(8) . ?
C25 N5 1.482(7) . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C26 N5 1.482(7) . ?
C26 C27 1.507(8) . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C27 N6 1.446(7) . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C28 N5 1.482(7) . ?
C28 C29 1.518(8) . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C29 N6 1.454(7) . ?
C29 H29A 0.98 . ?
C29 H29B 0.98 . ?
C30 N6 1.446(8) . ?
C30 H30A 0.97 . ?
C30 H30B 0.97 . ?
C30 H30C 0.97 . ?
C31 N7 1.465(7) . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C32 N7 1.479(7) . ?
C32 C33 1.490(8) . ?
C32 H32A 0.98 . ?
C32 H32B 0.98 . ?
C33 N8 1.487(7) . ?
C33 H33A 0.98 . ?
C33 H33B 0.98 . ?
C34 N7 1.473(7) . ?
C34 C35 1.516(8) . ?
C34 H34A 0.98 . ?
C34 H34B 0.98 . ?
C35 N8 1.477(7) . ?
C35 H35A 0.98 . ?
C35 H35B 0.98 . ?
C36 N8 1.480(8) . ?
C36 H36A 0.97 . ?
C36 H36B 0.97 . ?
C36 H36C 0.97 . ?
N2 H2 0.99 . ?
N3 Sb1 2.461(4) . ?
N5 Sb2 2.587(4) . ?
N8 H8 0.99 . ?
O1 Sb2 2.112(4) . ?
O1 Sb1 2.207(4) . ?
O1 H1A 0.84(4) . ?
O2 Sb2 1.991(3) . ?
O2 Sb1 1.994(3) . ?
Sb1 Sb2 3.2605(6) . ?
C37 F3 1.217(12) . ?
C37 F1 1.248(10) . ?
C37 F2 1.260(11) . ?
C37 C38 1.516(10) . ?
C38 O3 1.206(8) . ?
C38 O4 1.208(8) . ?
C39 F4 1.218(10) . ?
C39 F6 1.227(9) . ?
C39 F5 1.300(12) . ?
C39 C40 1.614(12) . ?
C40 O5 1.084(10) . ?
C40 O6 1.205(9) . ?
C41 F9 1.290(8) . ?
C41 F8 1.312(8) . ?
C41 F7 1.327(8) . ?
C41 C42 1.525(9) . ?
C42 O7 1.215(8) . ?
C42 O8 1.223(8) . ?
O9 H9C 0.84(4) . ?
O9 H9D 0.84(8) . ?
C43 C49 1.304(13) . ?
C43 C44 1.391(16) . ?
C43 C48 1.389(15) . ?
C44 C45 1.391(17) . ?
C44 H44 0.94 . ?
C45 C46 1.389(17) . ?
C45 H45 0.94 . ?
C46 C47 1.391(17) . ?
C46 H46 0.94 . ?
C47 C48 1.391(16) . ?
C47 H47 0.94 . ?
C48 H48 0.94 . ?
C49 H49A 0.97 . ?
C49 H49B 0.97 . ?
C49 H49C 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
C2 C1 C6 119.1(6) . . ?
C2 C1 Sb1 125.2(5) . . ?
C6 C1 Sb1 115.6(4) . . ?
C3 C2 C1 119.4(6) . . ?
C3 C2 C7 121.4(6) . . ?
C1 C2 C7 119.2(6) . . ?
C2 C3 C4 120.9(6) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.4(7) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.4(7) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.6(6) . . ?
C5 C6 C13 121.1(6) . . ?
C1 C6 C13 119.3(5) . . ?
N1 C7 C2 110.4(5) . . ?
N1 C7 H7A 109.6 . . ?
C2 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C2 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 C9 109.2(5) . . ?
N1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
N2 C9 C8 111.1(6) . . ?
N2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
N1 C10 C11 109.9(5) . . ?
N1 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N2 C11 C10 111.4(6) . . ?
N2 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C6 110.4(5) . . ?
N3 C13 H13A 109.6 . . ?
C6 C13 H13A 109.6 . . ?
N3 C13 H13B 109.6 . . ?
C6 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
N3 C14 C15 112.6(5) . . ?
N3 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
N4 C15 C14 110.8(5) . . ?
N4 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N3 C16 C17 111.9(5) . . ?
N3 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N3 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N4 C17 C16 109.9(5) . . ?
N4 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
N4 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 118.8(5) . . ?
C24 C19 Sb2 123.6(4) . . ?
C20 C19 Sb2 117.6(4) . . ?
C21 C20 C19 120.2(6) . . ?
C21 C20 C25 121.6(6) . . ?
C19 C20 C25 118.2(5) . . ?
C22 C21 C20 119.8(6) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.6(6) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 120.5(6) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 120.0(6) . . ?
C23 C24 C31 118.4(5) . . ?
C19 C24 C31 121.6(5) . . ?
N5 C25 C20 110.9(5) . . ?
N5 C25 H25A 109.5 . . ?
C20 C25 H25A 109.5 . . ?
N5 C25 H25B 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
N5 C26 C27 112.0(5) . . ?
N5 C26 H26A 109.2 . . ?
C27 C26 H26A 109.2 . . ?
N5 C26 H26B 109.2 . . ?
C27 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
N6 C27 C26 110.3(5) . . ?
N6 C27 H27A 109.6 . . ?
C26 C27 H27A 109.6 . . ?
N6 C27 H27B 109.6 . . ?
C26 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
N5 C28 C29 111.3(5) . . ?
N5 C28 H28A 109.4 . . ?
C29 C28 H28A 109.4 . . ?
N5 C28 H28B 109.4 . . ?
C29 C28 H28B 109.4 . . ?
H28A C28 H28B 108 . . ?
N6 C29 C28 110.0(5) . . ?
N6 C29 H29A 109.7 . . ?
C28 C29 H29A 109.7 . . ?
N6 C29 H29B 109.7 . . ?
C28 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
N6 C30 H30A 109.5 . . ?
N6 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N6 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N7 C31 C24 112.5(5) . . ?
N7 C31 H31A 109.1 . . ?
C24 C31 H31A 109.1 . . ?
N7 C31 H31B 109.1 . . ?
C24 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
N7 C32 C33 111.3(5) . . ?
N7 C32 H32A 109.4 . . ?
C33 C32 H32A 109.4 . . ?
N7 C32 H32B 109.4 . . ?
C33 C32 H32B 109.4 . . ?
H32A C32 H32B 108 . . ?
N8 C33 C32 111.0(5) . . ?
N8 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
N8 C33 H33B 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108 . . ?
N7 C34 C35 110.6(5) . . ?
N7 C34 H34A 109.5 . . ?
C35 C34 H34A 109.5 . . ?
N7 C34 H34B 109.5 . . ?
C35 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
N8 C35 C34 110.7(5) . . ?
N8 C35 H35A 109.5 . . ?
C34 C35 H35A 109.5 . . ?
N8 C35 H35B 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
N8 C36 H36A 109.5 . . ?
N8 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N8 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C8 N1 C7 109.6(5) . . ?
C8 N1 C10 109.7(5) . . ?
C7 N1 C10 111.1(5) . . ?
C12 N2 C9 112.0(6) . . ?
C12 N2 C11 112.3(6) . . ?
C9 N2 C11 109.6(5) . . ?
C12 N2 H2 107.6 . . ?
C9 N2 H2 107.6 . . ?
C11 N2 H2 107.6 . . ?
C13 N3 C16 110.4(4) . . ?
C13 N3 C14 110.9(5) . . ?
C16 N3 C14 108.1(4) . . ?
C13 N3 Sb1 102.9(3) . . ?
C16 N3 Sb1 113.0(3) . . ?
C14 N3 Sb1 111.4(3) . . ?
C15 N4 C17 109.8(4) . . ?
C15 N4 C18 111.3(5) . . ?
C17 N4 C18 111.1(5) . . ?
C28 N5 C26 109.0(4) . . ?
C28 N5 C25 109.1(4) . . ?
C26 N5 C25 108.8(4) . . ?
C28 N5 Sb2 115.7(3) . . ?
C26 N5 Sb2 114.9(3) . . ?
C25 N5 Sb2 98.6(3) . . ?
C30 N6 C27 110.8(5) . . ?
C30 N6 C29 111.1(5) . . ?
C27 N6 C29 108.4(5) . . ?
C31 N7 C34 109.8(4) . . ?
C31 N7 C32 110.5(5) . . ?
C34 N7 C32 109.0(4) . . ?
C35 N8 C36 112.4(5) . . ?
C35 N8 C33 109.9(4) . . ?
C36 N8 C33 112.0(5) . . ?
C35 N8 H8 107.4 . . ?
C36 N8 H8 107.4 . . ?
C33 N8 H8 107.4 . . ?
Sb2 O1 Sb1 98.04(15) . . ?
Sb2 O1 H1A 110(4) . . ?
Sb1 O1 H1A 110(4) . . ?
Sb2 O2 Sb1 109.83(16) . . ?
O2 Sb1 C1 90.34(19) . . ?
O2 Sb1 O1 74.92(14) . . ?
C1 Sb1 O1 94.77(18) . . ?
O2 Sb1 N3 81.51(14) . . ?
C1 Sb1 N3 74.31(18) . . ?
O1 Sb1 N3 154.00(14) . . ?
O2 Sb1 Sb2 35.06(10) . . ?
C1 Sb1 Sb2 92.07(15) . . ?
O1 Sb1 Sb2 39.89(10) . . ?
N3 Sb1 Sb2 115.67(10) . . ?
O2 Sb2 O1 77.17(14) . . ?
O2 Sb2 C19 103.04(17) . . ?
O1 Sb2 C19 86.66(18) . . ?
O2 Sb2 N5 77.43(14) . . ?
O1 Sb2 N5 142.60(14) . . ?
C19 Sb2 N5 72.92(18) . . ?
O2 Sb2 Sb1 35.12(10) . . ?
O1 Sb2 Sb1 42.08(10) . . ?
C19 Sb2 Sb1 95.94(14) . . ?
N5 Sb2 Sb1 108.11(10) . . ?
F3 C37 F1 104.5(10) . . ?
F3 C37 F2 99.0(10) . . ?
F1 C37 F2 105.7(10) . . ?
F3 C37 C38 112.1(10) . . ?
F1 C37 C38 117.8(8) . . ?
F2 C37 C38 115.6(9) . . ?
O3 C38 O4 130.5(7) . . ?
O3 C38 C37 115.3(7) . . ?
O4 C38 C37 114.0(7) . . ?
F4 C39 F6 112.0(11) . . ?
F4 C39 F5 100.5(9) . . ?
F6 C39 F5 102.8(9) . . ?
F4 C39 C40 115.6(8) . . ?
F6 C39 C40 110.4(7) . . ?
F5 C39 C40 114.5(10) . . ?
O5 C40 O6 136.0(12) . . ?
O5 C40 C39 111.6(9) . . ?
O6 C40 C39 111.6(9) . . ?
F9 C41 F8 108.7(8) . . ?
F9 C41 F7 105.4(7) . . ?
F8 C41 F7 103.3(6) . . ?
F9 C41 C42 114.4(6) . . ?
F8 C41 C42 111.4(6) . . ?
F7 C41 C42 112.8(7) . . ?
O7 C42 O8 127.4(7) . . ?
O7 C42 C41 116.0(7) . . ?
O8 C42 C41 116.5(7) . . ?
H9C O9 H9D 106(9) . . ?
C49 C43 C44 124.2(12) . . ?
C49 C43 C48 115.7(12) . . ?
C44 C43 C48 120.0(8) . . ?
C45 C44 C43 120.0(8) . . ?
C45 C44 H44 120 . . ?
C43 C44 H44 120 . . ?
C44 C45 C46 120.0(9) . . ?
C44 C45 H45 120 . . ?
C46 C45 H45 120 . . ?
C45 C46 C47 120.0(10) . . ?
C45 C46 H46 120 . . ?
C47 C46 H46 120 . . ?
C48 C47 C46 120.0(8) . . ?
C48 C47 H47 120 . . ?
C46 C47 H47 120 . . ?
C47 C48 C43 120.0(8) . . ?
C47 C48 H48 120 . . ?
C43 C48 H48 120 . . ?
C43 C49 H49A 109.5 . . ?
C43 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C43 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 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 -4.6(9) . . . . ?
Sb1 C1 C2 C3 173.1(5) . . . . ?
C6 C1 C2 C7 175.6(5) . . . . ?
Sb1 C1 C2 C7 -6.7(8) . . . . ?
C1 C2 C3 C4 1.6(10) . . . . ?
C7 C2 C3 C4 -178.6(6) . . . . ?
C2 C3 C4 C5 2.1(11) . . . . ?
C3 C4 C5 C6 -2.6(11) . . . . ?
C4 C5 C6 C1 -0.5(10) . . . . ?
C4 C5 C6 C13 179.1(6) . . . . ?
C2 C1 C6 C5 4.1(9) . . . . ?
Sb1 C1 C6 C5 -173.8(5) . . . . ?
C2 C1 C6 C13 -175.5(5) . . . . ?
Sb1 C1 C6 C13 6.6(7) . . . . ?
C3 C2 C7 N1 143.8(6) . . . . ?
C1 C2 C7 N1 -36.4(8) . . . . ?
N1 C8 C9 N2 58.8(7) . . . . ?
N1 C10 C11 N2 -58.3(7) . . . . ?
C5 C6 C13 N3 -151.7(6) . . . . ?
C1 C6 C13 N3 27.9(8) . . . . ?
N3 C14 C15 N4 -56.6(6) . . . . ?
N3 C16 C17 N4 59.7(6) . . . . ?
C24 C19 C20 C21 -2.9(8) . . . . ?
Sb2 C19 C20 C21 179.4(4) . . . . ?
C24 C19 C20 C25 177.0(5) . . . . ?
Sb2 C19 C20 C25 -0.7(7) . . . . ?
C19 C20 C21 C22 0.6(9) . . . . ?
C25 C20 C21 C22 -179.3(6) . . . . ?
C20 C21 C22 C23 2.9(10) . . . . ?
C21 C22 C23 C24 -3.9(9) . . . . ?
C22 C23 C24 C19 1.5(9) . . . . ?
C22 C23 C24 C31 -179.5(5) . . . . ?
C20 C19 C24 C23 1.9(8) . . . . ?
Sb2 C19 C24 C23 179.5(4) . . . . ?
C20 C19 C24 C31 -177.1(5) . . . . ?
Sb2 C19 C24 C31 0.4(7) . . . . ?
C21 C20 C25 N5 142.1(6) . . . . ?
C19 C20 C25 N5 -37.8(7) . . . . ?
N5 C26 C27 N6 58.6(7) . . . . ?
N5 C28 C29 N6 -59.2(6) . . . . ?
C23 C24 C31 N7 -140.9(5) . . . . ?
C19 C24 C31 N7 38.2(7) . . . . ?
N7 C32 C33 N8 -58.0(6) . . . . ?
N7 C34 C35 N8 58.3(6) . . . . ?
C9 C8 N1 C7 178.2(5) . . . . ?
C9 C8 N1 C10 -59.6(7) . . . . ?
C2 C7 N1 C8 -71.3(6) . . . . ?
C2 C7 N1 C10 167.3(5) . . . . ?
C11 C10 N1 C8 59.8(7) . . . . ?
C11 C10 N1 C7 -178.9(5) . . . . ?
C8 C9 N2 C12 178.1(6) . . . . ?
C8 C9 N2 C11 -56.6(7) . . . . ?
C10 C11 N2 C12 -178.3(5) . . . . ?
C10 C11 N2 C9 56.5(7) . . . . ?
C6 C13 N3 C16 -162.3(5) . . . . ?
C6 C13 N3 C14 77.8(6) . . . . ?
C6 C13 N3 Sb1 -41.4(5) . . . . ?
C17 C16 N3 C13 -176.4(5) . . . . ?
C17 C16 N3 C14 -54.9(6) . . . . ?
C17 C16 N3 Sb1 69.0(5) . . . . ?
C15 C14 N3 C13 174.4(5) . . . . ?
C15 C14 N3 C16 53.2(6) . . . . ?
C15 C14 N3 Sb1 -71.6(5) . . . . ?
C14 C15 N4 C17 59.0(6) . . . . ?
C14 C15 N4 C18 -177.6(5) . . . . ?
C16 C17 N4 C15 -60.5(6) . . . . ?
C16 C17 N4 C18 176.0(5) . . . . ?
C29 C28 N5 C26 53.7(6) . . . . ?
C29 C28 N5 C25 172.3(5) . . . . ?
C29 C28 N5 Sb2 -77.7(5) . . . . ?
C27 C26 N5 C28 -53.5(6) . . . . ?
C27 C26 N5 C25 -172.3(5) . . . . ?
C27 C26 N5 Sb2 78.3(5) . . . . ?
C20 C25 N5 C28 168.0(5) . . . . ?
C20 C25 N5 C26 -73.2(6) . . . . ?
C20 C25 N5 Sb2 46.9(5) . . . . ?
C26 C27 N6 C30 176.2(5) . . . . ?
C26 C27 N6 C29 -61.6(6) . . . . ?
C28 C29 N6 C30 -176.0(5) . . . . ?
C28 C29 N6 C27 62.0(6) . . . . ?
C24 C31 N7 C34 -169.3(5) . . . . ?
C24 C31 N7 C32 70.4(6) . . . . ?
C35 C34 N7 C31 -179.5(5) . . . . ?
C35 C34 N7 C32 -58.3(6) . . . . ?
C33 C32 N7 C31 179.3(5) . . . . ?
C33 C32 N7 C34 58.6(6) . . . . ?
C34 C35 N8 C36 178.4(5) . . . . ?
C34 C35 N8 C33 -56.1(6) . . . . ?
C32 C33 N8 C35 56.2(6) . . . . ?
C32 C33 N8 C36 -178.1(5) . . . . ?
F3 C37 C38 O3 78.7(14) . . . . ?
F1 C37 C38 O3 -160.0(10) . . . . ?
F2 C37 C38 O3 -33.7(14) . . . . ?
F3 C37 C38 O4 -97.7(12) . . . . ?
F1 C37 C38 O4 23.7(14) . . . . ?
F2 C37 C38 O4 149.9(11) . . . . ?
F4 C39 C40 O5 -178.0(12) . . . . ?
F6 C39 C40 O5 53.6(15) . . . . ?
F5 C39 C40 O5 -61.9(13) . . . . ?
F4 C39 C40 O6 -6.8(15) . . . . ?
F6 C39 C40 O6 -135.1(10) . . . . ?
F5 C39 C40 O6 109.4(11) . . . . ?
F9 C41 C42 O7 40.2(11) . . . . ?
F8 C41 C42 O7 -83.5(8) . . . . ?
F7 C41 C42 O7 160.7(7) . . . . ?
F9 C41 C42 O8 -138.3(8) . . . . ?
F8 C41 C42 O8 97.9(9) . . . . ?
F7 C41 C42 O8 -17.8(10) . . . . ?
C49 C43 C44 C45 -174.8(11) . . . . ?
C48 C43 C44 C45 0 . . . . ?
C43 C44 C45 C46 0 . . . . ?
C44 C45 C46 C47 0.1(14) . . . . ?
C45 C46 C47 C48 -0.1(13) . . . . ?
C46 C47 C48 C43 0.1(12) . . . . ?
C49 C43 C48 C47 175.2(10) . . . . ?
C44 C43 C48 C47 -0.1(12) . . . . ?

_shelxl_version_number           2013-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1041687'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_date             2014-08-20T08:36:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H29 N4 O4 Sb, H2 O'
_chemical_formula_sum            'C20 H31 N4 O5 Sb'
_chemical_formula_weight         529.24

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0558(19)
_cell_length_b                   17.283(4)
_cell_length_c                   16.433(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.629(4)
_cell_angle_gamma                90
_cell_volume                     2476.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3800
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      21.13
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.148
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.683
_shelx_estimated_absorpt_T_max   0.762

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

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_number            23884
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.745
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             4590
_reflns_number_gt                3793
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.6313P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4590
_refine_ls_number_parameters     281
_refine_ls_number_restraints     3
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.085

#----------------------------------------------------------------------------#
#                   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'
Sb Sb -0.5866 1.5461 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4851(5) 0.4327(2) 0.3484(3) 0.0391(10) Uani 1 d . .
C2 C 0.5426(5) 0.4024(2) 0.4299(3) 0.0418(10) Uani 1 d . .
C3 C 0.4485(6) 0.4017(3) 0.4846(3) 0.0539(12) Uani 1 d . .
H3 H 0.4853 0.3818 0.5389 0.065 Uiso 1 calc . .
C4 C 0.3009(6) 0.4305(3) 0.4586(4) 0.0626(15) Uani 1 d . .
H4 H 0.2402 0.4315 0.4961 0.075 Uiso 1 calc . .
C5 C 0.2425(6) 0.4579(3) 0.3764(3) 0.0556(13) Uani 1 d . .
H5 H 0.1419 0.4755 0.3588 0.067 Uiso 1 calc . .
C6 C 0.3330(5) 0.4593(2) 0.3210(3) 0.0423(10) Uani 1 d . .
C7 C 0.7042(5) 0.3707(2) 0.4558(3) 0.0479(11) Uani 1 d . .
H7A H 0.775 0.4117 0.4808 0.057 Uiso 1 calc . .
H7B H 0.7114 0.3306 0.498 0.057 Uiso 1 calc . .
C8 C 0.6728(5) 0.2624(2) 0.3562(3) 0.0434(10) Uani 1 d . .
H8A H 0.5623 0.2687 0.3411 0.052 Uiso 1 calc . .
H8B H 0.7013 0.2266 0.4033 0.052 Uiso 1 calc . .
C9 C 0.7198(5) 0.2293(2) 0.2818(3) 0.0449(10) Uani 1 d . .
H9A H 0.6712 0.1793 0.2671 0.054 Uiso 1 calc . .
H9B H 0.6846 0.2633 0.2335 0.054 Uiso 1 calc . .
C10 C 0.9162(5) 0.3287(2) 0.4010(3) 0.0484(11) Uani 1 d . .
H10A H 0.9513 0.2942 0.449 0.058 Uiso 1 calc . .
H10B H 0.9657 0.3784 0.416 0.058 Uiso 1 calc . .
C11 C 0.9610(5) 0.2958(3) 0.3257(3) 0.0529(12) Uani 1 d . .
H11A H 0.9309 0.3316 0.2786 0.063 Uiso 1 calc . .
H11B H 1.0715 0.2896 0.3397 0.063 Uiso 1 calc . .
C12 C 0.9305(6) 0.1891(3) 0.2269(3) 0.0767(16) Uani 1 d . .
H12A H 0.9018 0.2253 0.1809 0.115 Uiso 1 calc . .
H12B H 0.8788 0.1408 0.2102 0.115 Uiso 1 calc . .
H12C H 1.0393 0.181 0.2415 0.115 Uiso 1 calc . .
C13 C 0.2713(5) 0.4849(2) 0.2305(3) 0.0449(10) Uani 1 d . .
H13A H 0.1609 0.4781 0.2132 0.054 Uiso 1 calc . .
H13B H 0.293 0.5394 0.226 0.054 Uiso 1 calc . .
C14 C 0.2739(5) 0.3608(2) 0.1618(3) 0.0427(10) Uani 1 d . .
H14A H 0.1633 0.3646 0.1405 0.051 Uiso 1 calc . .
H14B H 0.2969 0.3344 0.2158 0.051 Uiso 1 calc . .
C15 C 0.3359(5) 0.3133(2) 0.1004(3) 0.0461(10) Uani 1 d . .
H15A H 0.4453 0.3056 0.1235 0.055 Uiso 1 calc . .
H15B H 0.2869 0.2629 0.0926 0.055 Uiso 1 calc . .
C16 C 0.3138(5) 0.4777(2) 0.0903(3) 0.0443(10) Uani 1 d . .
H16 H 0.362 0.5283 0.0971 0.053 Uiso 1 calc . .
H16B H 0.2046 0.4849 0.0661 0.053 Uiso 1 calc . .
C17 C 0.3778(5) 0.4296(2) 0.0309(3) 0.0471(11) Uani 1 d . .
H17 H 0.3591 0.4558 -0.0231 0.057 Uiso 1 calc . .
H17B H 0.4877 0.4242 0.054 0.057 Uiso 1 calc . .
C18 C 0.3674(6) 0.3069(3) -0.0408(3) 0.0718(15) Uani 1 d . .
H18A H 0.4766 0.3019 -0.0192 0.108 Uiso 1 calc . .
H18B H 0.3439 0.3324 -0.0947 0.108 Uiso 1 calc . .
H18C H 0.3212 0.2565 -0.0472 0.108 Uiso 1 calc . .
C19 C 0.8036(5) 0.5718(2) 0.3459(3) 0.0439(10) Uani 1 d . .
C20 C 0.6705(5) 0.6057(2) 0.2752(3) 0.0414(10) Uani 1 d . .
N1 N 0.7475(4) 0.33827(18) 0.3819(2) 0.0386(8) Uani 1 d . .
N2 N 0.8866(4) 0.2203(2) 0.3008(2) 0.0503(9) Uani 1 d . .
N3 N 0.3408(4) 0.44010(16) 0.1741(2) 0.0377(8) Uani 1 d . .
N4 N 0.3069(4) 0.35293(19) 0.0186(2) 0.0457(9) Uani 1 d . .
O1 O 0.8035(3) 0.49647(15) 0.35005(18) 0.0459(7) Uani 1 d . .
O2 O 0.5756(3) 0.55417(14) 0.2328(2) 0.0454(7) Uani 1 d . .
O3 O 0.8973(4) 0.61319(18) 0.39300(19) 0.0641(9) Uani 1 d . .
O4 O 0.6592(4) 0.67437(18) 0.2618(2) 0.0663(10) Uani 1 d . .
Sb1 Sb 0.62641(3) 0.43600(2) 0.26285(2) 0.03497(11) Uani 1 d . .
O5 O -0.0039(4) 0.3879(2) -0.0629(3) 0.0903(13) Uani 1 d . .
H5A H 0.081(3) 0.370(3) -0.036(3) 0.108 Uiso 1 d . .
H5B H -0.039(6) 0.357(3) -0.103(2) 0.108 Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.401(6) . ?
C1 C6 1.406(6) . ?
C1 Sb1 2.142(4) . ?
C2 C3 1.396(6) . ?
C2 C7 1.512(6) . ?
C3 C4 1.381(7) . ?
C3 H3 0.93 . ?
C4 C5 1.394(7) . ?
C4 H4 0.93 . ?
C5 C6 1.379(6) . ?
C5 H5 0.93 . ?
C6 C13 1.507(6) . ?
C7 N1 1.483(5) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 N1 1.484(5) . ?
C8 C9 1.511(6) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N2 1.465(5) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 N1 1.484(5) . ?
C10 C11 1.513(6) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N2 1.476(5) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 N2 1.477(6) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 N3 1.473(5) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 N3 1.490(5) . ?
C14 C15 1.520(5) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 N4 1.467(5) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 N3 1.483(5) . ?
C16 C17 1.510(6) . ?
C16 H16 0.97 . ?
C16 H16B 0.97 . ?
C17 N4 1.463(5) . ?
C17 H17 0.97 . ?
C17 H17B 0.97 . ?
C18 N4 1.474(5) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 O3 1.215(5) . ?
C19 O1 1.305(4) . ?
C19 C20 1.546(6) . ?
C20 O4 1.206(5) . ?
C20 O2 1.302(5) . ?
N1 Sb1 2.593(3) . ?
N3 Sb1 2.605(3) . ?
O1 Sb1 2.117(3) . ?
O2 Sb1 2.122(3) . ?
O5 H5A 0.84(4) . ?
O5 H5B 0.84(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.6(4) . . ?
C2 C1 Sb1 120.2(3) . . ?
C6 C1 Sb1 119.2(3) . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 C7 121.9(4) . . ?
C1 C2 C7 119.2(4) . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.2(4) . . ?
C5 C6 C13 121.9(4) . . ?
C1 C6 C13 118.9(4) . . ?
N1 C7 C2 110.8(3) . . ?
N1 C7 H7A 109.5 . . ?
C2 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 C9 111.0(3) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108 . . ?
N2 C9 C8 111.5(3) . . ?
N2 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108 . . ?
N1 C10 C11 110.9(3) . . ?
N1 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C10 110.8(4) . . ?
N2 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C6 111.1(3) . . ?
N3 C13 H13A 109.4 . . ?
C6 C13 H13A 109.4 . . ?
N3 C13 H13B 109.4 . . ?
C6 C13 H13B 109.4 . . ?
H13A C13 H13B 108 . . ?
N3 C14 C15 112.2(3) . . ?
N3 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N4 C15 C14 110.4(3) . . ?
N4 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N4 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N3 C16 C17 111.3(3) . . ?
N3 C16 H16 109.4 . . ?
C17 C16 H16 109.4 . . ?
N3 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16 C16 H16B 108 . . ?
N4 C17 C16 111.0(3) . . ?
N4 C17 H17 109.4 . . ?
C16 C17 H17 109.4 . . ?
N4 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17 C17 H17B 108 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 O1 124.3(4) . . ?
O3 C19 C20 121.7(4) . . ?
O1 C19 C20 114.0(3) . . ?
O4 C20 O2 124.3(4) . . ?
O4 C20 C19 121.4(4) . . ?
O2 C20 C19 114.3(3) . . ?
C7 N1 C8 111.5(3) . . ?
C7 N1 C10 110.7(3) . . ?
C8 N1 C10 109.0(3) . . ?
C7 N1 Sb1 102.7(2) . . ?
C8 N1 Sb1 107.1(2) . . ?
C10 N1 Sb1 115.7(2) . . ?
C9 N2 C11 109.4(3) . . ?
C9 N2 C12 110.7(4) . . ?
C11 N2 C12 110.3(4) . . ?
C13 N3 C16 111.3(3) . . ?
C13 N3 C14 110.0(3) . . ?
C16 N3 C14 108.5(3) . . ?
C13 N3 Sb1 100.9(2) . . ?
C16 N3 Sb1 115.0(2) . . ?
C14 N3 Sb1 110.9(2) . . ?
C17 N4 C15 109.4(3) . . ?
C17 N4 C18 110.7(4) . . ?
C15 N4 C18 110.4(3) . . ?
C19 O1 Sb1 117.9(3) . . ?
C20 O2 Sb1 117.6(3) . . ?
O1 Sb1 O2 76.09(11) . . ?
O1 Sb1 C1 92.66(13) . . ?
O2 Sb1 C1 92.74(13) . . ?
O1 Sb1 N1 73.84(10) . . ?
O2 Sb1 N1 145.42(11) . . ?
C1 Sb1 N1 72.15(13) . . ?
O1 Sb1 N3 145.33(10) . . ?
O2 Sb1 N3 73.94(10) . . ?
C1 Sb1 N3 71.93(14) . . ?
N1 Sb1 N3 126.45(10) . . ?
H5A O5 H5B 106(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 -2.4(6) . . . . ?
Sb1 C1 C2 C3 179.4(3) . . . . ?
C6 C1 C2 C7 177.0(3) . . . . ?
Sb1 C1 C2 C7 -1.2(5) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C7 C2 C3 C4 -179.4(4) . . . . ?
C2 C3 C4 C5 2.3(7) . . . . ?
C3 C4 C5 C6 -2.3(7) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C4 C5 C6 C13 176.9(4) . . . . ?
C2 C1 C6 C5 2.5(6) . . . . ?
Sb1 C1 C6 C5 -179.3(3) . . . . ?
C2 C1 C6 C13 -174.7(3) . . . . ?
Sb1 C1 C6 C13 3.6(5) . . . . ?
C3 C2 C7 N1 148.7(4) . . . . ?
C1 C2 C7 N1 -30.6(5) . . . . ?
N1 C8 C9 N2 57.8(4) . . . . ?
N1 C10 C11 N2 -58.7(4) . . . . ?
C5 C6 C13 N3 -144.8(4) . . . . ?
C1 C6 C13 N3 32.3(5) . . . . ?
N3 C14 C15 N4 -57.2(4) . . . . ?
N3 C16 C17 N4 59.5(4) . . . . ?
O3 C19 C20 O4 3.6(7) . . . . ?
O1 C19 C20 O4 -177.2(4) . . . . ?
O3 C19 C20 O2 -176.8(4) . . . . ?
O1 C19 C20 O2 2.4(5) . . . . ?
C2 C7 N1 C8 -75.2(4) . . . . ?
C2 C7 N1 C10 163.3(3) . . . . ?
C2 C7 N1 Sb1 39.2(3) . . . . ?
C9 C8 N1 C7 -179.0(3) . . . . ?
C9 C8 N1 C10 -56.5(4) . . . . ?
C9 C8 N1 Sb1 69.3(3) . . . . ?
C11 C10 N1 C7 -179.8(3) . . . . ?
C11 C10 N1 C8 57.2(4) . . . . ?
C11 C10 N1 Sb1 -63.5(4) . . . . ?
C8 C9 N2 C11 -57.3(4) . . . . ?
C8 C9 N2 C12 -179.1(4) . . . . ?
C10 C11 N2 C9 57.6(4) . . . . ?
C10 C11 N2 C12 179.7(4) . . . . ?
C6 C13 N3 C16 -164.9(3) . . . . ?
C6 C13 N3 C14 74.8(4) . . . . ?
C6 C13 N3 Sb1 -42.4(3) . . . . ?
C17 C16 N3 C13 -177.0(3) . . . . ?
C17 C16 N3 C14 -55.8(4) . . . . ?
C17 C16 N3 Sb1 69.1(3) . . . . ?
C15 C14 N3 C13 177.1(3) . . . . ?
C15 C14 N3 C16 55.1(4) . . . . ?
C15 C14 N3 Sb1 -72.1(4) . . . . ?
C16 C17 N4 C15 -59.4(4) . . . . ?
C16 C17 N4 C18 178.8(4) . . . . ?
C14 C15 N4 C17 57.8(4) . . . . ?
C14 C15 N4 C18 179.8(4) . . . . ?
O3 C19 O1 Sb1 178.9(3) . . . . ?
C20 C19 O1 Sb1 -0.4(4) . . . . ?
O4 C20 O2 Sb1 176.3(3) . . . . ?
C19 C20 O2 Sb1 -3.3(4) . . . . ?

_shelxl_version_number           2013-3



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1041688'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_date             2014-08-20T19:59:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H33 N4 O2 Sb, 2(H2 O)'
_chemical_formula_sum            'C20 H37 N4 O4 Sb'
_chemical_formula_weight         519.28

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.626(3)
_cell_length_b                   12.291(3)
_cell_length_c                   15.792(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.53(3)
_cell_angle_gamma                90
_cell_volume                     2416.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.172
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.758
_shelx_estimated_absorpt_T_max   0.817

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.2051
_diffrn_reflns_number            23681
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.917
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             4502
_reflns_number_gt                3293
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+5.0340P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0023(8)
_refine_ls_number_reflns         4502
_refine_ls_number_parameters     277
_refine_ls_number_restraints     6
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1519
_refine_ls_R_factor_gt           0.1086
_refine_ls_wR_factor_ref         0.2261
_refine_ls_wR_factor_gt          0.2069
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_restrained_S_all      1.191
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.493
_refine_diff_density_min         -2.062
_refine_diff_density_rms         0.161

#----------------------------------------------------------------------------#
#                   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'
Sb Sb -0.5866 1.5461 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4280(8) 0.0129(9) 0.1944(6) 0.033(3) Uani 1 d . .
C2 C 0.3978(9) -0.0720(8) 0.2438(7) 0.033(3) Uani 1 d . .
C3 C 0.4476(11) -0.1719(11) 0.2408(9) 0.056(4) Uani 1 d . .
H3 H 0.4268 -0.2296 0.2724 0.067 Uiso 1 calc . .
C4 C 0.5269(12) -0.1881(10) 0.1921(9) 0.060(4) Uani 1 d . .
H4 H 0.5591 -0.256 0.1909 0.072 Uiso 1 calc . .
C5 C 0.5581(9) -0.1036(11) 0.1455(8) 0.049(3) Uani 1 d . .
H5 H 0.6113 -0.1147 0.112 0.058 Uiso 1 calc . .
C6 C 0.5098(8) 0.0022(9) 0.1475(7) 0.034(3) Uani 1 d . .
C7 C 0.3116(9) -0.0540(9) 0.2993(7) 0.042(3) Uani 1 d . .
H7A H 0.241 -0.0601 0.2643 0.05 Uiso 1 calc . .
H7B H 0.3176 -0.109 0.3438 0.05 Uiso 1 calc . .
C8 C 0.4192(9) 0.0582(9) 0.4060(7) 0.039(3) Uani 1 d . .
H8A H 0.4829 0.0422 0.3813 0.047 Uiso 1 calc . .
H8B H 0.4125 0.0028 0.4486 0.047 Uiso 1 calc . .
C9 C 0.4316(9) 0.1690(10) 0.4493(8) 0.044(3) Uani 1 d . .
H9A H 0.4937 0.168 0.4947 0.053 Uiso 1 calc . .
H9B H 0.4439 0.2236 0.4077 0.053 Uiso 1 calc . .
C10 C 0.2265(9) 0.0883(11) 0.3736(7) 0.047(3) Uani 1 d . .
H10A H 0.2109 0.0348 0.415 0.056 Uiso 1 calc . .
H10B H 0.1655 0.0917 0.3274 0.056 Uiso 1 calc . .
C11 C 0.2444(9) 0.2000(10) 0.4170(7) 0.042(3) Uani 1 d . .
H11A H 0.2559 0.254 0.3747 0.05 Uiso 1 calc . .
H11B H 0.1807 0.2206 0.4401 0.05 Uiso 1 calc . .
C12 C 0.3508(12) 0.2994(12) 0.5297(9) 0.065(4) Uani 1 d . .
H12A H 0.3991 0.2899 0.5829 0.098 Uiso 1 calc . .
H12B H 0.2828 0.3251 0.5412 0.098 Uiso 1 calc . .
H12C H 0.3803 0.3515 0.4948 0.098 Uiso 1 calc . .
C13 C 0.5454(9) 0.0967(10) 0.0980(8) 0.046(3) Uani 1 d . .
H13A H 0.618 0.0838 0.0876 0.055 Uiso 1 calc . .
H13B H 0.4988 0.1025 0.0428 0.055 Uiso 1 calc . .
C14 C 0.6276(9) 0.2027(9) 0.2208(7) 0.039(3) Uani 1 d . .
H14A H 0.6967 0.1957 0.2021 0.047 Uiso 1 calc . .
H14B H 0.619 0.1417 0.2581 0.047 Uiso 1 calc . .
C15 C 0.6236(10) 0.3103(9) 0.2705(8) 0.045(3) Uani 1 d . .
H15A H 0.557 0.3139 0.2934 0.054 Uiso 1 calc . .
H15B H 0.6825 0.3121 0.3185 0.054 Uiso 1 calc . .
C16 C 0.5506(10) 0.2957(10) 0.0925(8) 0.048(3) Uani 1 d . .
H16A H 0.493 0.2945 0.0436 0.058 Uiso 1 calc . .
H16B H 0.6184 0.2938 0.0713 0.058 Uiso 1 calc . .
C17 C 0.5437(9) 0.3983(9) 0.1435(8) 0.043(3) Uani 1 d . .
H17A H 0.5461 0.461 0.1065 0.051 Uiso 1 calc . .
H17B H 0.4759 0.3999 0.1647 0.051 Uiso 1 calc . .
C18 C 0.6236(12) 0.5047(11) 0.2639(9) 0.070(4) Uani 1 d . .
H18A H 0.6809 0.5066 0.3121 0.105 Uiso 1 calc . .
H18B H 0.5559 0.5067 0.2839 0.105 Uiso 1 calc . .
H18C H 0.6293 0.5665 0.2277 0.105 Uiso 1 calc . .
C19 C 0.1520(12) 0.1049(15) 0.0897(10) 0.081(5) Uani 1 d . .
H19A H 0.0997 0.1631 0.0776 0.097 Uiso 1 calc . .
H19B H 0.114 0.0366 0.0779 0.097 Uiso 1 calc . .
C20 C 0.2305(12) 0.1155(13) 0.0318(8) 0.065(4) Uani 1 d . .
H20A H 0.2606 0.0446 0.0231 0.078 Uiso 1 calc . .
H20B H 0.1949 0.1422 -0.0234 0.078 Uiso 1 calc . .
N1 N 0.3247(7) 0.0550(8) 0.3385(5) 0.036(2) Uani 1 d . .
N2 N 0.3363(8) 0.1982(8) 0.4856(6) 0.041(2) Uani 1 d . .
N3 N 0.5421(7) 0.2013(7) 0.1466(5) 0.029(2) Uani 1 d . .
N4 N 0.6311(8) 0.4044(8) 0.2149(6) 0.045(3) Uani 1 d . .
O1 O 0.1965(6) 0.1084(7) 0.1773(5) 0.046(2) Uani 1 d . .
O2 O 0.3140(6) 0.1878(7) 0.0656(5) 0.048(2) Uani 1 d . .
Sb1 Sb 0.34681(6) 0.17027(6) 0.19658(5) 0.0327(3) Uani 1 d . .
O3 O 0.3075(7) 0.0357(8) 0.6171(6) 0.061(2) Uani 1 d . .
H3A H 0.319(9) 0.085(8) 0.583(6) 0.073 Uiso 1 d . .
H3B H 0.246(5) 0.011(10) 0.598(7) 0.073 Uiso 1 d . .
O4 O 0.8136(13) 0.1592(13) 0.4269(8) 0.113(5) Uani 1 d . .
H4A H 0.755(6) 0.152(17) 0.445(10) 0.135 Uiso 1 d . .
H4B H 0.862(9) 0.156(18) 0.471(7) 0.135 Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 C6 1.374(14) . ?
C1 C2 1.393(14) . ?
C1 Sb1 2.192(11) . ?
C2 C3 1.384(16) . ?
C2 C7 1.522(15) . ?
C3 C4 1.373(19) . ?
C3 H3 0.93 . ?
C4 C5 1.369(18) . ?
C4 H4 0.93 . ?
C5 C6 1.439(15) . ?
C5 H5 0.93 . ?
C6 C13 1.510(16) . ?
C7 N1 1.474(14) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 N1 1.463(12) . ?
C8 C9 1.520(15) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N2 1.461(14) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 N1 1.496(14) . ?
C10 C11 1.535(17) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N2 1.451(15) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 N2 1.423(15) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 N3 1.501(14) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 N3 1.456(13) . ?
C14 C15 1.543(15) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 N4 1.465(14) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 N3 1.454(14) . ?
C16 C17 1.506(17) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 N4 1.443(14) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 N4 1.467(15) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 O1 1.405(16) . ?
C19 C20 1.461(19) . ?
C19 H19A 0.97 . ?
C19 H19B 0.97 . ?
C20 O2 1.414(15) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
O1 Sb1 2.021(7) . ?
O2 Sb1 2.052(8) . ?
O3 H3A 0.84(10) . ?
O3 H3B 0.84(7) . ?
O4 H4A 0.84(10) . ?
O4 H4B 0.85(12) . ?

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 C1 C2 122.1(10) . . ?
C6 C1 Sb1 119.2(8) . . ?
C2 C1 Sb1 118.7(8) . . ?
C3 C2 C1 118.5(11) . . ?
C3 C2 C7 121.4(10) . . ?
C1 C2 C7 120.1(10) . . ?
C4 C3 C2 121.7(12) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 119.5(12) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.8(11) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.2(11) . . ?
C1 C6 C13 121.4(10) . . ?
C5 C6 C13 121.3(10) . . ?
N1 C7 C2 109.5(9) . . ?
N1 C7 H7A 109.8 . . ?
C2 C7 H7A 109.8 . . ?
N1 C7 H7B 109.8 . . ?
C2 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
N1 C8 C9 111.3(9) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108 . . ?
N2 C9 C8 111.5(10) . . ?
N2 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108 . . ?
N1 C10 C11 109.9(9) . . ?
N1 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N2 C11 C10 111.1(10) . . ?
N2 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C6 111.0(9) . . ?
N3 C13 H13A 109.4 . . ?
C6 C13 H13A 109.4 . . ?
N3 C13 H13B 109.4 . . ?
C6 C13 H13B 109.4 . . ?
H13A C13 H13B 108 . . ?
N3 C14 C15 109.7(9) . . ?
N3 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
N3 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
N4 C15 C14 111.2(10) . . ?
N4 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
N4 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108 . . ?
N3 C16 C17 109.8(10) . . ?
N3 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
N3 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N4 C17 C16 110.9(10) . . ?
N4 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 C20 114.3(12) . . ?
O1 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
O1 C19 H19B 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
O2 C20 C19 111.1(11) . . ?
O2 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
O2 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108 . . ?
C8 N1 C7 110.6(8) . . ?
C8 N1 C10 110.4(9) . . ?
C7 N1 C10 111.2(9) . . ?
C12 N2 C11 112.0(10) . . ?
C12 N2 C9 111.0(10) . . ?
C11 N2 C9 108.6(9) . . ?
C16 N3 C14 110.3(9) . . ?
C16 N3 C13 111.9(9) . . ?
C14 N3 C13 110.0(8) . . ?
C17 N4 C15 108.1(9) . . ?
C17 N4 C18 110.4(10) . . ?
C15 N4 C18 109.3(10) . . ?
C19 O1 Sb1 111.8(8) . . ?
C20 O2 Sb1 109.2(7) . . ?
O1 Sb1 O2 81.9(3) . . ?
O1 Sb1 C1 95.5(4) . . ?
O2 Sb1 C1 95.4(3) . . ?
H3A O3 H3B 106(11) . . ?
H4A O4 H4B 106(12) . . ?

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 -4.2(16) . . . . ?
Sb1 C1 C2 C3 178.6(8) . . . . ?
C6 C1 C2 C7 176.0(10) . . . . ?
Sb1 C1 C2 C7 -1.2(13) . . . . ?
C1 C2 C3 C4 1.5(18) . . . . ?
C7 C2 C3 C4 -178.7(12) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C3 C4 C5 C6 0.7(19) . . . . ?
C2 C1 C6 C5 5.0(15) . . . . ?
Sb1 C1 C6 C5 -177.8(7) . . . . ?
C2 C1 C6 C13 -176.8(10) . . . . ?
Sb1 C1 C6 C13 0.4(14) . . . . ?
C4 C5 C6 C1 -3.2(17) . . . . ?
C4 C5 C6 C13 178.6(11) . . . . ?
C3 C2 C7 N1 141.2(11) . . . . ?
C1 C2 C7 N1 -39.0(13) . . . . ?
N1 C8 C9 N2 57.5(13) . . . . ?
N1 C10 C11 N2 -58.4(12) . . . . ?
C1 C6 C13 N3 37.6(14) . . . . ?
C5 C6 C13 N3 -144.2(10) . . . . ?
N3 C14 C15 N4 -56.6(12) . . . . ?
N3 C16 C17 N4 61.7(12) . . . . ?
O1 C19 C20 O2 -36(2) . . . . ?
C9 C8 N1 C7 -178.0(9) . . . . ?
C9 C8 N1 C10 -54.4(12) . . . . ?
C2 C7 N1 C8 -72.2(11) . . . . ?
C2 C7 N1 C10 164.6(9) . . . . ?
C11 C10 N1 C8 54.6(12) . . . . ?
C11 C10 N1 C7 177.8(9) . . . . ?
C10 C11 N2 C12 -176.9(9) . . . . ?
C10 C11 N2 C9 60.2(11) . . . . ?
C8 C9 N2 C12 177.1(10) . . . . ?
C8 C9 N2 C11 -59.4(12) . . . . ?
C17 C16 N3 C14 -58.8(12) . . . . ?
C17 C16 N3 C13 178.4(9) . . . . ?
C15 C14 N3 C16 56.2(12) . . . . ?
C15 C14 N3 C13 -179.9(9) . . . . ?
C6 C13 N3 C16 -166.1(9) . . . . ?
C6 C13 N3 C14 70.9(11) . . . . ?
C16 C17 N4 C15 -60.5(12) . . . . ?
C16 C17 N4 C18 179.9(10) . . . . ?
C14 C15 N4 C17 58.0(13) . . . . ?
C14 C15 N4 C18 178.3(10) . . . . ?
C20 C19 O1 Sb1 16.8(17) . . . . ?
C19 C20 O2 Sb1 35.9(15) . . . . ?

_shelxl_version_number           2013-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1041689'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_date             2014-08-25T21:21:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H33 Bi N4 O2, 2(H2 O)'
_chemical_formula_sum            'C20 H37 Bi N4 O4'
_chemical_formula_weight         606.51

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.6247(9)
_cell_length_b                   12.1795(9)
_cell_length_c                   15.7589(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.4150(10)
_cell_angle_gamma                90
_cell_volume                     2390.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5396
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      22.41
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    7.406
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.259
_shelx_estimated_absorpt_T_max   0.305

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

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_number            23158
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.921
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             4445
_reflns_number_gt                3738
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+0.1679P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4445
_refine_ls_number_parameters     276
_refine_ls_number_restraints     6
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0723
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.724
_refine_diff_density_min         -1.053
_refine_diff_density_rms         0.111

#----------------------------------------------------------------------------#
#                   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'
Bi Bi -4.1077 10.2566 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5716(4) 0.5117(4) 0.3055(3) 0.0337(12) Uani 1 d . .
C2 C 0.6005(4) 0.4262(4) 0.2571(4) 0.0396(14) Uani 1 d . .
C3 C 0.5508(5) 0.3260(5) 0.2595(4) 0.0532(17) Uani 1 d . .
H3 H 0.5706 0.2679 0.2271 0.064 Uiso 1 calc . .
C4 C 0.4725(6) 0.3109(5) 0.3089(5) 0.062(2) Uani 1 d . .
H4 H 0.4409 0.2423 0.3114 0.074 Uiso 1 calc . .
C5 C 0.4404(5) 0.3976(5) 0.3551(4) 0.0527(17) Uani 1 d . .
H5 H 0.3857 0.3875 0.3874 0.063 Uiso 1 calc . .
C6 C 0.4891(4) 0.5003(4) 0.3538(4) 0.0400(14) Uani 1 d . .
C7 C 0.6870(5) 0.4437(4) 0.2014(4) 0.0448(15) Uani 1 d . .
H7A H 0.7574 0.4369 0.2365 0.054 Uiso 1 calc . .
H7B H 0.6807 0.3879 0.157 0.054 Uiso 1 calc . .
C8 C 0.5820(4) 0.5558(5) 0.0937(4) 0.0427(14) Uani 1 d . .
H8A H 0.518 0.5397 0.1182 0.051 Uiso 1 calc . .
H8B H 0.5891 0.4999 0.0511 0.051 Uiso 1 calc . .
C9 C 0.5706(5) 0.6670(4) 0.0510(4) 0.0446(14) Uani 1 d . .
H9A H 0.5091 0.6663 0.0052 0.054 Uiso 1 calc . .
H9B H 0.5578 0.7219 0.0927 0.054 Uiso 1 calc . .
C10 C 0.7719(4) 0.5846(5) 0.1258(4) 0.0473(15) Uani 1 d . .
H10A H 0.7851 0.5312 0.0831 0.057 Uiso 1 calc . .
H10B H 0.8339 0.5854 0.1713 0.057 Uiso 1 calc . .
C11 C 0.7569(5) 0.6958(5) 0.0854(4) 0.0496(16) Uani 1 d . .
H11A H 0.7447 0.7492 0.1285 0.06 Uiso 1 calc . .
H11B H 0.8217 0.7168 0.0638 0.06 Uiso 1 calc . .
C12 C 0.6537(6) 0.8026(5) -0.0270(5) 0.069(2) Uani 1 d . .
H12A H 0.7218 0.8272 -0.0395 0.104 Uiso 1 calc . .
H12B H 0.627 0.8548 0.01 0.104 Uiso 1 calc . .
H12C H 0.6037 0.7961 -0.0797 0.104 Uiso 1 calc . .
C13 C 0.4569(5) 0.5965(4) 0.4037(4) 0.0433(14) Uani 1 d . .
H13A H 0.3856 0.584 0.4172 0.052 Uiso 1 calc . .
H13B H 0.5063 0.6033 0.4574 0.052 Uiso 1 calc . .
C14 C 0.3699(5) 0.7021(4) 0.2808(4) 0.0402(14) Uani 1 d . .
H14A H 0.3015 0.6965 0.301 0.048 Uiso 1 calc . .
H14B H 0.3763 0.6398 0.2436 0.048 Uiso 1 calc . .
C15 C 0.3732(5) 0.8081(4) 0.2302(4) 0.0428(14) Uani 1 d . .
H15A H 0.4392 0.811 0.2062 0.051 Uiso 1 calc . .
H15B H 0.3134 0.8095 0.1829 0.051 Uiso 1 calc . .
C16 C 0.4494(5) 0.7955(4) 0.4090(4) 0.0469(15) Uani 1 d . .
H16A H 0.5078 0.7946 0.4573 0.056 Uiso 1 calc . .
H16B H 0.3823 0.7932 0.4313 0.056 Uiso 1 calc . .
C17 C 0.4545(5) 0.8981(5) 0.3585(4) 0.0500(16) Uani 1 d . .
H17A H 0.4501 0.9611 0.3954 0.06 Uiso 1 calc . .
H17B H 0.5229 0.9014 0.338 0.06 Uiso 1 calc . .
C18 C 0.3718(6) 1.0036(5) 0.2357(5) 0.070(2) Uani 1 d . .
H18A H 0.3647 1.066 0.2716 0.105 Uiso 1 calc . .
H18B H 0.3144 1.0037 0.1875 0.105 Uiso 1 calc . .
H18C H 0.4394 1.0073 0.2153 0.105 Uiso 1 calc . .
C19 C 0.8543(5) 0.6105(7) 0.4141(4) 0.071(2) Uani 1 d . .
H19A H 0.902 0.6733 0.4236 0.086 Uiso 1 calc . .
H19B H 0.8972 0.5451 0.4288 0.086 Uiso 1 calc . .
C20 C 0.7769(6) 0.6186(7) 0.4707(4) 0.070(2) Uani 1 d . .
H20A H 0.7492 0.5458 0.4791 0.084 Uiso 1 calc . .
H20B H 0.8126 0.6448 0.5262 0.084 Uiso 1 calc . .
N1 N 0.6759(3) 0.5528(4) 0.1616(3) 0.0365(11) Uani 1 d . .
N2 N 0.6668(4) 0.6967(4) 0.0154(3) 0.0453(12) Uani 1 d . .
N3 N 0.4572(3) 0.6991(3) 0.3545(3) 0.0351(11) Uani 1 d . .
N4 N 0.3673(4) 0.9032(4) 0.2852(3) 0.0456(12) Uani 1 d . .
O1 O 0.8108(3) 0.6060(3) 0.3272(2) 0.0501(10) Uani 1 d . .
O2 O 0.6908(3) 0.6882(3) 0.4413(2) 0.0504(11) Uani 1 d . .
Bi1 Bi 0.65289(2) 0.67434(2) 0.30256(2) 0.03398(8) Uani 1 d . .
O3 O 0.3086(4) 0.4674(3) 0.1163(3) 0.0593(12) Uani 1 d . .
H3A H 0.327(5) 0.422(3) 0.081(3) 0.071 Uiso 1 d . .
H3B H 0.278(5) 0.432(4) 0.151(3) 0.071 Uiso 1 d . .
O4 O 0.3182(6) 0.1576(6) 0.4284(4) 0.103(2) Uani 1 d . .
H4A H 0.253(2) 0.168(7) 0.431(6) 0.124 Uiso 1 d . .
H4B H 0.341(6) 0.123(7) 0.474(4) 0.124 Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.375(7) . ?
C1 C6 1.393(7) . ?
C1 Bi1 2.235(5) . ?
C2 C3 1.376(7) . ?
C2 C7 1.524(8) . ?
C3 C4 1.367(9) . ?
C3 H3 0.93 . ?
C4 C5 1.381(9) . ?
C4 H4 0.93 . ?
C5 C6 1.396(7) . ?
C5 H5 0.93 . ?
C6 C13 1.504(7) . ?
C7 N1 1.466(7) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 N1 1.461(6) . ?
C8 C9 1.509(7) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N2 1.464(7) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 N1 1.470(6) . ?
C10 C11 1.496(8) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N2 1.450(7) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 N2 1.450(7) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 N3 1.470(6) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 N3 1.465(7) . ?
C14 C15 1.522(7) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 N4 1.456(7) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 N3 1.467(6) . ?
C16 C17 1.489(8) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 N4 1.461(7) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 N4 1.456(7) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 O1 1.390(7) . ?
C19 C20 1.430(8) . ?
C19 H19A 0.97 . ?
C19 H19B 0.97 . ?
C20 O2 1.397(8) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
N1 Bi1 2.725(4) . ?
N3 Bi1 2.744(4) . ?
O1 Bi1 2.136(4) . ?
O2 Bi1 2.167(4) . ?
O3 H3A 0.84(5) . ?
O3 H3B 0.84(5) . ?
O4 H4A 0.84(4) . ?
O4 H4B 0.84(7) . ?

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 C1 C6 121.1(5) . . ?
C2 C1 Bi1 119.7(4) . . ?
C6 C1 Bi1 119.1(4) . . ?
C1 C2 C3 119.6(6) . . ?
C1 C2 C7 119.6(5) . . ?
C3 C2 C7 120.8(5) . . ?
C4 C3 C2 120.7(6) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.0(6) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
C4 C5 C6 120.6(6) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.9(5) . . ?
C1 C6 C13 119.9(5) . . ?
C5 C6 C13 122.2(5) . . ?
N1 C7 C2 110.3(4) . . ?
N1 C7 H7A 109.6 . . ?
C2 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C2 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 C9 110.8(4) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N2 C9 C8 111.6(5) . . ?
N2 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108 . . ?
N1 C10 C11 110.3(5) . . ?
N1 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N1 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C10 111.1(5) . . ?
N2 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C6 111.2(5) . . ?
N3 C13 H13A 109.4 . . ?
C6 C13 H13A 109.4 . . ?
N3 C13 H13B 109.4 . . ?
C6 C13 H13B 109.4 . . ?
H13A C13 H13B 108 . . ?
N3 C14 C15 110.8(4) . . ?
N3 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N4 C15 C14 110.7(5) . . ?
N4 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N3 C16 C17 110.3(5) . . ?
N3 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
N3 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N4 C17 C16 111.4(5) . . ?
N4 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
N4 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 C20 114.6(5) . . ?
O1 C19 H19A 108.6 . . ?
C20 C19 H19A 108.6 . . ?
O1 C19 H19B 108.6 . . ?
C20 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
O2 C20 C19 114.2(6) . . ?
O2 C20 H20A 108.7 . . ?
C19 C20 H20A 108.7 . . ?
O2 C20 H20B 108.7 . . ?
C19 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C8 N1 C7 110.2(4) . . ?
C8 N1 C10 109.5(4) . . ?
C7 N1 C10 112.1(4) . . ?
C8 N1 Bi1 113.6(3) . . ?
C7 N1 Bi1 99.1(3) . . ?
C10 N1 Bi1 112.0(3) . . ?
C12 N2 C11 111.9(5) . . ?
C12 N2 C9 111.0(5) . . ?
C11 N2 C9 107.7(4) . . ?
C14 N3 C16 109.3(4) . . ?
C14 N3 C13 111.9(4) . . ?
C16 N3 C13 111.4(4) . . ?
C14 N3 Bi1 111.3(3) . . ?
C16 N3 Bi1 114.3(3) . . ?
C13 N3 Bi1 98.3(3) . . ?
C15 N4 C18 109.8(5) . . ?
C15 N4 C17 109.4(4) . . ?
C18 N4 C17 111.6(5) . . ?
C19 O1 Bi1 111.7(3) . . ?
C20 O2 Bi1 108.6(3) . . ?
O1 Bi1 O2 78.54(15) . . ?
O1 Bi1 C1 93.97(17) . . ?
O2 Bi1 C1 94.27(17) . . ?
O1 Bi1 N1 73.49(13) . . ?
O2 Bi1 N1 146.07(14) . . ?
C1 Bi1 N1 69.27(16) . . ?
O1 Bi1 N3 147.94(14) . . ?
O2 Bi1 N3 75.59(14) . . ?
C1 Bi1 N3 69.63(16) . . ?
N1 Bi1 N3 121.63(13) . . ?
H3A O3 H3B 107(3) . . ?
H4A O4 H4B 104(8) . . ?

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 -3.1(8) . . . . ?
Bi1 C1 C2 C3 179.6(4) . . . . ?
C6 C1 C2 C7 176.8(5) . . . . ?
Bi1 C1 C2 C7 -0.6(7) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C7 C2 C3 C4 -179.4(6) . . . . ?
C2 C3 C4 C5 2.0(10) . . . . ?
C3 C4 C5 C6 -1.8(10) . . . . ?
C2 C1 C6 C5 3.2(8) . . . . ?
Bi1 C1 C6 C5 -179.5(4) . . . . ?
C2 C1 C6 C13 -178.0(5) . . . . ?
Bi1 C1 C6 C13 -0.6(7) . . . . ?
C4 C5 C6 C1 -0.8(8) . . . . ?
C4 C5 C6 C13 -179.6(6) . . . . ?
C1 C2 C7 N1 -38.8(7) . . . . ?
C3 C2 C7 N1 141.0(5) . . . . ?
N1 C8 C9 N2 57.4(6) . . . . ?
N1 C10 C11 N2 -60.9(6) . . . . ?
C1 C6 C13 N3 39.9(7) . . . . ?
C5 C6 C13 N3 -141.3(5) . . . . ?
N3 C14 C15 N4 -57.3(6) . . . . ?
N3 C16 C17 N4 59.7(6) . . . . ?
O1 C19 C20 O2 -40.2(10) . . . . ?
C9 C8 N1 C7 -179.0(5) . . . . ?
C9 C8 N1 C10 -55.2(6) . . . . ?
C9 C8 N1 Bi1 70.8(5) . . . . ?
C2 C7 N1 C8 -72.4(5) . . . . ?
C2 C7 N1 C10 165.4(4) . . . . ?
C2 C7 N1 Bi1 47.1(4) . . . . ?
C11 C10 N1 C8 57.0(6) . . . . ?
C11 C10 N1 C7 179.6(5) . . . . ?
C11 C10 N1 Bi1 -70.0(5) . . . . ?
C10 C11 N2 C12 -177.6(5) . . . . ?
C10 C11 N2 C9 60.3(6) . . . . ?
C8 C9 N2 C12 178.8(5) . . . . ?
C8 C9 N2 C11 -58.4(6) . . . . ?
C15 C14 N3 C16 57.1(6) . . . . ?
C15 C14 N3 C13 -179.0(4) . . . . ?
C15 C14 N3 Bi1 -70.1(5) . . . . ?
C17 C16 N3 C14 -58.3(6) . . . . ?
C17 C16 N3 C13 177.6(5) . . . . ?
C17 C16 N3 Bi1 67.3(5) . . . . ?
C6 C13 N3 C14 69.9(6) . . . . ?
C6 C13 N3 C16 -167.4(5) . . . . ?
C6 C13 N3 Bi1 -47.1(5) . . . . ?
C14 C15 N4 C18 179.3(5) . . . . ?
C14 C15 N4 C17 56.6(6) . . . . ?
C16 C17 N4 C15 -58.4(6) . . . . ?
C16 C17 N4 C18 179.9(5) . . . . ?
C20 C19 O1 Bi1 22.5(8) . . . . ?
C19 C20 O2 Bi1 35.4(8) . . . . ?

_shelxl_version_number           2013-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1041690'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_date             2014-08-20T08:27:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24  H41  N4  O2  Sb1'
_chemical_formula_sum            'C24 H41 N4 O2 Sb'
_chemical_formula_weight         539.36

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.188(9)
_cell_length_b                   11.022(9)
_cell_length_c                   21.870(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.335(15)
_cell_angle_gamma                90
_cell_volume                     2692(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2930
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      20.16
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.27
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.05
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.704
_shelx_estimated_absorpt_T_max   0.765

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

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_number            24813
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.626
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_number_total             4980
_reflns_number_gt                3708
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4980
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.71
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.082

#----------------------------------------------------------------------------#
#                   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'
Sb Sb -0.5866 1.5461 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9302(4) 0.4447(5) 0.3356(2) 0.0487(13) Uani 1 d . .
C2 C 1.0034(5) 0.3482(6) 0.3199(2) 0.0644(16) Uani 1 d . .
C3 C 1.1228(6) 0.3673(8) 0.3101(3) 0.089(2) Uani 1 d . .
H3 H 1.1696 0.302 0.2991 0.107 Uiso 1 calc . .
C4 C 1.1731(6) 0.4771(10) 0.3161(3) 0.108(3) Uani 1 d . .
H4 H 1.2534 0.4881 0.3086 0.129 Uiso 1 calc . .
C5 C 1.1037(6) 0.5750(7) 0.3338(3) 0.095(2) Uani 1 d . .
H5 H 1.1383 0.6512 0.3396 0.114 Uiso 1 calc . .
C6 C 0.9828(5) 0.5582(5) 0.3427(2) 0.0606(15) Uani 1 d . .
C7 C 0.9514(5) 0.2236(6) 0.3145(3) 0.0732(18) Uani 1 d . .
H7A H 0.9096 0.2146 0.2746 0.088 Uiso 1 calc . .
H7B H 1.0155 0.1643 0.3175 0.088 Uiso 1 calc . .
C8 C 0.9367(6) 0.1814(6) 0.4217(3) 0.0826(19) Uani 1 d . .
H8A H 0.9849 0.2526 0.4315 0.099 Uiso 1 calc . .
H8B H 0.9899 0.1125 0.4187 0.099 Uiso 1 calc . .
C9 C 0.8512(7) 0.1591(6) 0.4715(3) 0.095(2) Uani 1 d . .
H9A H 0.8963 0.1485 0.5104 0.114 Uiso 1 calc . .
H9B H 0.7994 0.229 0.475 0.114 Uiso 1 calc . .
C10 C 0.7905(6) 0.0939(4) 0.3494(3) 0.0711(18) Uani 1 d . .
H10A H 0.8398 0.0229 0.3435 0.085 Uiso 1 calc . .
H10B H 0.7417 0.1078 0.3119 0.085 Uiso 1 calc . .
C11 C 0.7112(6) 0.0714(5) 0.4010(3) 0.0767(19) Uani 1 d . .
H11A H 0.6596 0.1412 0.4054 0.092 Uiso 1 calc . .
H11B H 0.6606 0.0018 0.3911 0.092 Uiso 1 calc . .
C12 C 0.7000(8) 0.0289(7) 0.5069(4) 0.129(3) Uani 1 d . .
H12A H 0.6486 0.0979 0.5109 0.194 Uiso 1 calc . .
H12B H 0.7474 0.017 0.5444 0.194 Uiso 1 calc . .
H12C H 0.6522 -0.042 0.4981 0.194 Uiso 1 calc . .
C13 C 0.9060(5) 0.6638(5) 0.3586(3) 0.0724(18) Uani 1 d . .
H13A H 0.9562 0.727 0.3773 0.087 Uiso 1 calc . .
H13B H 0.8673 0.6965 0.3213 0.087 Uiso 1 calc . .
C14 C 0.8685(5) 0.6075(5) 0.4626(2) 0.0681(16) Uani 1 d . .
H14A H 0.9133 0.6787 0.4764 0.082 Uiso 1 calc . .
H14B H 0.9242 0.5402 0.4611 0.082 Uiso 1 calc . .
C15 C 0.7757(6) 0.5788(6) 0.5077(3) 0.0742(17) Uani 1 d . .
H15A H 0.7356 0.5037 0.4958 0.089 Uiso 1 calc . .
H15B H 0.8149 0.5673 0.548 0.089 Uiso 1 calc . .
C16 C 0.7206(5) 0.7234(4) 0.4039(3) 0.0690(17) Uani 1 d . .
H16A H 0.68 0.733 0.3638 0.083 Uiso 1 calc . .
H16B H 0.7579 0.8003 0.4153 0.083 Uiso 1 calc . .
C17 C 0.6308(6) 0.6914(5) 0.4495(3) 0.0764(18) Uani 1 d . .
H17A H 0.5713 0.7553 0.4504 0.092 Uiso 1 calc . .
H17B H 0.5902 0.617 0.4368 0.092 Uiso 1 calc . .
C18 C 0.5986(7) 0.6497(7) 0.5555(3) 0.111(3) Uani 1 d . .
H18A H 0.5418 0.7149 0.5558 0.166 Uiso 1 calc . .
H18B H 0.6384 0.6418 0.5954 0.166 Uiso 1 calc . .
H18C H 0.5577 0.5754 0.5448 0.166 Uiso 1 calc . .
C19 C 0.6800(5) 0.3969(4) 0.2174(2) 0.0522(13) Uani 1 d . .
C20 C 0.6151(4) 0.5105(4) 0.2400(2) 0.0520(13) Uani 1 d . .
C21 C 0.7984(5) 0.4340(5) 0.1896(3) 0.0716(17) Uani 1 d . .
H21A H 0.8454 0.3629 0.1829 0.107 Uiso 1 calc . .
H21B H 0.8423 0.4876 0.2172 0.107 Uiso 1 calc . .
H21C H 0.781 0.4746 0.1512 0.107 Uiso 1 calc . .
C22 C 0.6046(5) 0.3221(5) 0.1719(2) 0.0645(15) Uani 1 d . .
H22A H 0.573 0.3734 0.1394 0.097 Uiso 1 calc . .
H22B H 0.5398 0.2855 0.1921 0.097 Uiso 1 calc . .
H22C H 0.6531 0.2598 0.1553 0.097 Uiso 1 calc . .
C23 C 0.6025(5) 0.6134(5) 0.1932(3) 0.0739(18) Uani 1 d . .
H23A H 0.6797 0.6484 0.1876 0.111 Uiso 1 calc . .
H23B H 0.5499 0.6745 0.2077 0.111 Uiso 1 calc . .
H23C H 0.5699 0.582 0.1548 0.111 Uiso 1 calc . .
C24 C 0.4881(4) 0.4775(5) 0.2604(3) 0.0691(16) Uani 1 d . .
H24A H 0.4364 0.4599 0.225 0.104 Uiso 1 calc . .
H24B H 0.4563 0.5447 0.2822 0.104 Uiso 1 calc . .
H24C H 0.4934 0.4077 0.2867 0.104 Uiso 1 calc . .
N1 N 0.8678(4) 0.1998(4) 0.36248(18) 0.0581(12) Uani 1 d . .
N2 N 0.7775(6) 0.0497(4) 0.4578(3) 0.0934(18) Uani 1 d . .
N3 N 0.8135(4) 0.6295(4) 0.40099(18) 0.0516(11) Uani 1 d . .
N4 N 0.6872(5) 0.6755(4) 0.5104(2) 0.0745(14) Uani 1 d . .
O1 O 0.7067(3) 0.3231(3) 0.27008(13) 0.0485(8) Uani 1 d . .
O2 O 0.6841(3) 0.5544(3) 0.29237(14) 0.0512(9) Uani 1 d . .
Sb1 Sb 0.74210(3) 0.41849(3) 0.34739(2) 0.04308(13) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 C6 1.388(7) . ?
C1 C2 1.397(7) . ?
C1 Sb1 2.155(5) . ?
C2 C3 1.381(8) . ?
C2 C7 1.494(8) . ?
C3 C4 1.337(10) . ?
C3 H3 0.93 . ?
C4 C5 1.398(10) . ?
C4 H4 0.93 . ?
C5 C6 1.390(8) . ?
C5 H5 0.93 . ?
C6 C13 1.499(8) . ?
C7 N1 1.470(6) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 N1 1.481(6) . ?
C8 C9 1.511(8) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N2 1.482(7) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 N1 1.471(6) . ?
C10 C11 1.495(8) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N2 1.430(7) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 N2 1.437(9) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 N3 1.479(6) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 N3 1.469(6) . ?
C14 C15 1.505(8) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 N4 1.458(7) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 N3 1.471(6) . ?
C16 C17 1.497(7) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 N4 1.451(7) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 N4 1.467(7) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 O1 1.427(5) . ?
C19 C22 1.512(6) . ?
C19 C20 1.543(7) . ?
C19 C21 1.545(7) . ?
C20 O2 1.428(5) . ?
C20 C23 1.529(7) . ?
C20 C24 1.557(7) . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
C22 H22A 0.96 . ?
C22 H22B 0.96 . ?
C22 H22C 0.96 . ?
C23 H23A 0.96 . ?
C23 H23B 0.96 . ?
C23 H23C 0.96 . ?
C24 H24A 0.96 . ?
C24 H24B 0.96 . ?
C24 H24C 0.96 . ?
O1 Sb1 2.011(3) . ?
O2 Sb1 2.005(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.6(5) . . ?
C6 C1 Sb1 121.2(4) . . ?
C2 C1 Sb1 121.2(4) . . ?
C3 C2 C1 120.5(6) . . ?
C3 C2 C7 120.3(6) . . ?
C1 C2 C7 119.2(5) . . ?
C4 C3 C2 121.9(7) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.3(7) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 119.8(7) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C6 C5 120.9(6) . . ?
C1 C6 C13 118.7(5) . . ?
C5 C6 C13 120.3(6) . . ?
N1 C7 C2 111.6(4) . . ?
N1 C7 H7A 109.3 . . ?
C2 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C2 C7 H7B 109.3 . . ?
H7A C7 H7B 108 . . ?
N1 C8 C9 109.5(5) . . ?
N1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C8 110.7(5) . . ?
N2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 C11 110.6(4) . . ?
N1 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C10 112.5(6) . . ?
N2 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C6 112.2(4) . . ?
N3 C13 H13A 109.2 . . ?
C6 C13 H13A 109.2 . . ?
N3 C13 H13B 109.2 . . ?
C6 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N3 C14 C15 111.5(5) . . ?
N3 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
N3 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108 . . ?
N4 C15 C14 111.7(5) . . ?
N4 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
N4 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
N3 C16 C17 111.5(4) . . ?
N3 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N3 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108 . . ?
N4 C17 C16 111.5(5) . . ?
N4 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
N4 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 C22 107.7(4) . . ?
O1 C19 C20 106.6(4) . . ?
C22 C19 C20 113.4(4) . . ?
O1 C19 C21 109.0(4) . . ?
C22 C19 C21 110.1(4) . . ?
C20 C19 C21 110.0(4) . . ?
O2 C20 C23 108.1(4) . . ?
O2 C20 C19 106.8(4) . . ?
C23 C20 C19 114.5(5) . . ?
O2 C20 C24 108.0(4) . . ?
C23 C20 C24 108.4(4) . . ?
C19 C20 C24 110.9(4) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 N1 C10 113.2(4) . . ?
C7 N1 C8 109.2(5) . . ?
C10 N1 C8 109.4(4) . . ?
C11 N2 C12 111.8(7) . . ?
C11 N2 C9 107.1(5) . . ?
C12 N2 C9 109.3(5) . . ?
C14 N3 C16 109.6(4) . . ?
C14 N3 C13 110.3(4) . . ?
C16 N3 C13 111.7(4) . . ?
C17 N4 C15 108.1(4) . . ?
C17 N4 C18 111.5(5) . . ?
C15 N4 C18 111.9(5) . . ?
C19 O1 Sb1 113.7(3) . . ?
C20 O2 Sb1 111.7(3) . . ?
O2 Sb1 O1 81.09(14) . . ?
O2 Sb1 C1 96.47(16) . . ?
O1 Sb1 C1 96.63(16) . . ?

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 -1.8(8) . . . . ?
Sb1 C1 C2 C3 177.4(4) . . . . ?
C6 C1 C2 C7 177.4(5) . . . . ?
Sb1 C1 C2 C7 -3.4(6) . . . . ?
C1 C2 C3 C4 0.9(9) . . . . ?
C7 C2 C3 C4 -178.2(6) . . . . ?
C2 C3 C4 C5 1.2(11) . . . . ?
C3 C4 C5 C6 -2.3(10) . . . . ?
C2 C1 C6 C5 0.6(8) . . . . ?
Sb1 C1 C6 C5 -178.6(4) . . . . ?
C2 C1 C6 C13 178.9(4) . . . . ?
Sb1 C1 C6 C13 -0.3(6) . . . . ?
C4 C5 C6 C1 1.4(9) . . . . ?
C4 C5 C6 C13 -176.8(6) . . . . ?
C3 C2 C7 N1 139.8(5) . . . . ?
C1 C2 C7 N1 -39.4(7) . . . . ?
N1 C8 C9 N2 60.2(7) . . . . ?
N1 C10 C11 N2 -59.4(6) . . . . ?
C1 C6 C13 N3 36.8(7) . . . . ?
C5 C6 C13 N3 -144.8(5) . . . . ?
N3 C14 C15 N4 -57.2(6) . . . . ?
N3 C16 C17 N4 58.7(6) . . . . ?
O1 C19 C20 O2 47.9(5) . . . . ?
C22 C19 C20 O2 166.2(4) . . . . ?
C21 C19 C20 O2 -70.0(5) . . . . ?
O1 C19 C20 C23 167.5(4) . . . . ?
C22 C19 C20 C23 -74.2(6) . . . . ?
C21 C19 C20 C23 49.6(6) . . . . ?
O1 C19 C20 C24 -69.4(5) . . . . ?
C22 C19 C20 C24 48.9(6) . . . . ?
C21 C19 C20 C24 172.6(4) . . . . ?
C2 C7 N1 C10 164.2(4) . . . . ?
C2 C7 N1 C8 -73.8(6) . . . . ?
C11 C10 N1 C7 177.7(4) . . . . ?
C11 C10 N1 C8 55.7(6) . . . . ?
C9 C8 N1 C7 179.0(5) . . . . ?
C9 C8 N1 C10 -56.7(6) . . . . ?
C10 C11 N2 C12 179.7(5) . . . . ?
C10 C11 N2 C9 60.0(7) . . . . ?
C8 C9 N2 C11 -60.5(7) . . . . ?
C8 C9 N2 C12 178.2(6) . . . . ?
C15 C14 N3 C16 53.6(6) . . . . ?
C15 C14 N3 C13 177.0(5) . . . . ?
C17 C16 N3 C14 -54.4(6) . . . . ?
C17 C16 N3 C13 -176.9(4) . . . . ?
C6 C13 N3 C14 72.4(5) . . . . ?
C6 C13 N3 C16 -165.5(4) . . . . ?
C16 C17 N4 C15 -59.2(6) . . . . ?
C16 C17 N4 C18 177.3(5) . . . . ?
C14 C15 N4 C17 58.5(6) . . . . ?
C14 C15 N4 C18 -178.3(5) . . . . ?
C22 C19 O1 Sb1 -155.2(3) . . . . ?
C20 C19 O1 Sb1 -33.2(4) . . . . ?
C21 C19 O1 Sb1 85.4(4) . . . . ?
C23 C20 O2 Sb1 -165.5(3) . . . . ?
C19 C20 O2 Sb1 -41.8(4) . . . . ?
C24 C20 O2 Sb1 77.4(4) . . . . ?

_shelxl_version_number           2013-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1041691'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_date             2014-11-21T16:06:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C24 H33 N4 O2 Sb'
_chemical_formula_sum            'C24 H33 N4 O2 Sb'
_chemical_formula_weight         531.29

#----------------------------------------------------------------------------#
#                   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                   9.7365(11)
_cell_length_b                   10.1979(11)
_cell_length_c                   15.6619(18)
_cell_angle_alpha                81.563(2)
_cell_angle_beta                 76.977(2)
_cell_angle_gamma                64.391(2)
_cell_volume                     1364.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3978
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      22.61
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.43
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544

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

_exptl_absorpt_coefficient_mu    1.035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_T_max  0.662
_shelx_estimated_absorpt_T_min   0.58
_shelx_estimated_absorpt_T_max   0.665

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

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_number            13491
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.337
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_number_total             5028
_reflns_number_gt                4374
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+0.3021P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5028
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   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'
Sb Sb -0.5866 1.5461 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3395(4) 0.0764(4) 0.1990(2) 0.0454(9) Uani 1 d . .
C2 C 0.3281(4) 0.0877(4) 0.1111(2) 0.0504(9) Uani 1 d . .
C3 C 0.3388(4) -0.0305(5) 0.0726(3) 0.0627(11) Uani 1 d . .
H3 H 0.3311 -0.0227 0.0138 0.075 Uiso 1 calc . .
C4 C 0.3606(5) -0.1602(5) 0.1210(3) 0.0674(12) Uani 1 d . .
H4 H 0.3703 -0.2404 0.0945 0.081 Uiso 1 calc . .
C5 C 0.3682(5) -0.1703(5) 0.2086(3) 0.0622(11) Uani 1 d . .
H5 H 0.3806 -0.257 0.2416 0.075 Uiso 1 calc . .
C6 C 0.3575(4) -0.0528(4) 0.2481(2) 0.0493(9) Uani 1 d . .
C7 C 0.2997(5) 0.2321(4) 0.0598(2) 0.0573(10) Uani 1 d . .
H7A H 0.3975 0.2398 0.0379 0.069 Uiso 1 calc . .
H7B H 0.2538 0.237 0.0099 0.069 Uiso 1 calc . .
C8 C 0.0375(4) 0.3611(4) 0.1319(3) 0.0501(9) Uani 1 d . .
H8A H 0.0358 0.2745 0.1664 0.06 Uiso 1 calc . .
H8B H 0.0086 0.3626 0.0763 0.06 Uiso 1 calc . .
C9 C -0.0781(4) 0.4932(4) 0.1794(3) 0.0563(10) Uani 1 d . .
H9A H -0.1809 0.4958 0.187 0.068 Uiso 1 calc . .
H9B H -0.0546 0.4878 0.2372 0.068 Uiso 1 calc . .
C10 C 0.1972(5) 0.4913(4) 0.0719(3) 0.0553(10) Uani 1 d . .
H10A H 0.1764 0.501 0.0131 0.066 Uiso 1 calc . .
H10B H 0.2991 0.4893 0.0671 0.066 Uiso 1 calc . .
C11 C 0.0776(5) 0.6209(4) 0.1222(3) 0.0581(10) Uani 1 d . .
H11A H 0.1017 0.6144 0.1799 0.07 Uiso 1 calc . .
H11B H 0.0802 0.7098 0.0914 0.07 Uiso 1 calc . .
C12 C -0.1959(5) 0.7559(5) 0.1740(3) 0.0758(13) Uani 1 d . .
H12A H -0.1864 0.841 0.1432 0.114 Uiso 1 calc . .
H12B H -0.1837 0.7516 0.2337 0.114 Uiso 1 calc . .
H12C H -0.2961 0.7604 0.1732 0.114 Uiso 1 calc . .
C13 C 0.3642(5) -0.0611(4) 0.3434(3) 0.0554(10) Uani 1 d . .
H13A H 0.3376 -0.1394 0.3734 0.066 Uiso 1 calc . .
H13B H 0.4692 -0.0836 0.3494 0.066 Uiso 1 calc . .
C14 C 0.0982(4) 0.0930(4) 0.3945(2) 0.0520(10) Uani 1 d . .
H14A H 0.0883 0.0066 0.425 0.062 Uiso 1 calc . .
H14B H 0.0727 0.103 0.3368 0.062 Uiso 1 calc . .
C15 C -0.0145(4) 0.2251(4) 0.4451(3) 0.0582(11) Uani 1 d . .
H15A H -0.0102 0.3124 0.4127 0.07 Uiso 1 calc . .
H15B H -0.119 0.2325 0.4515 0.07 Uiso 1 calc . .
C16 C 0.2942(5) 0.0751(4) 0.4713(2) 0.0548(10) Uani 1 d . .
H16A H 0.3969 0.0727 0.4638 0.066 Uiso 1 calc . .
H16B H 0.2941 -0.0118 0.5061 0.066 Uiso 1 calc . .
C17 C 0.1778(5) 0.2080(5) 0.5194(3) 0.0604(11) Uani 1 d . .
H17A H 0.2037 0.2046 0.5762 0.072 Uiso 1 calc . .
H17B H 0.1813 0.2949 0.4862 0.072 Uiso 1 calc . .
C18 C -0.0911(6) 0.3355(6) 0.5843(3) 0.0914(16) Uani 1 d . .
H18A H -0.1919 0.3364 0.5908 0.137 Uiso 1 calc . .
H18B H -0.0919 0.4257 0.5557 0.137 Uiso 1 calc . .
H18C H -0.0642 0.3237 0.6412 0.137 Uiso 1 calc . .
C19 C 0.6265(4) 0.2134(4) 0.1711(2) 0.0482(9) Uani 1 d . .
C20 C 0.6474(4) 0.1358(4) 0.2516(2) 0.0443(8) Uani 1 d . .
C21 C 0.7948(5) 0.0517(4) 0.2671(3) 0.0552(10) Uani 1 d . .
H21 H 0.8092 0.0053 0.3221 0.066 Uiso 1 calc . .
C22 C 0.9224(5) 0.0352(5) 0.2014(3) 0.0634(11) Uani 1 d . .
H22 H 1.022 -0.0232 0.2117 0.076 Uiso 1 calc . .
C23 C 0.8994(5) 0.1067(5) 0.1205(3) 0.0630(11) Uani 1 d . .
H23 H 0.9842 0.0944 0.0757 0.076 Uiso 1 calc . .
C24 C 0.7519(5) 0.1967(5) 0.1051(3) 0.0581(11) Uani 1 d . .
H24 H 0.7376 0.2454 0.0506 0.07 Uiso 1 calc . .
N1 N 0.1955(3) 0.3540(3) 0.11566(18) 0.0438(7) Uani 1 d . .
N2 N -0.0757(4) 0.6256(3) 0.1312(2) 0.0528(8) Uani 1 d . .
N3 N 0.2587(3) 0.0752(3) 0.38501(19) 0.0447(7) Uani 1 d . .
N4 N 0.0233(4) 0.2142(4) 0.5313(2) 0.0585(9) Uani 1 d . .
O1 O 0.4803(3) 0.3014(3) 0.16124(17) 0.0613(7) Uani 1 d . .
O2 O 0.5178(3) 0.1517(3) 0.31213(16) 0.0521(6) Uani 1 d . .
Sb1 Sb 0.31866(3) 0.26311(3) 0.25847(2) 0.04530(11) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 C6 1.387(5) . ?
C1 C2 1.390(5) . ?
C1 Sb1 2.153(4) . ?
C2 C3 1.380(5) . ?
C2 C7 1.513(5) . ?
C3 C4 1.380(6) . ?
C3 H3 0.93 . ?
C4 C5 1.378(6) . ?
C4 H4 0.93 . ?
C5 C6 1.382(5) . ?
C5 H5 0.93 . ?
C6 C13 1.497(5) . ?
C7 N1 1.473(5) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 N1 1.473(4) . ?
C8 C9 1.497(5) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N2 1.453(5) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 N1 1.471(5) . ?
C10 C11 1.511(5) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N2 1.448(5) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 N2 1.466(5) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 N3 1.463(5) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 N3 1.469(4) . ?
C14 C15 1.513(5) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 N4 1.455(5) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 N3 1.468(4) . ?
C16 C17 1.508(5) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 N4 1.448(5) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 N4 1.467(5) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 O1 1.345(4) . ?
C19 C24 1.375(5) . ?
C19 C20 1.393(5) . ?
C20 O2 1.358(4) . ?
C20 C21 1.373(5) . ?
C21 C22 1.388(6) . ?
C21 H21 0.93 . ?
C22 C23 1.379(6) . ?
C22 H22 0.93 . ?
C23 C24 1.384(6) . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
O1 Sb1 2.056(2) . ?
O2 Sb1 2.075(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
C6 C1 C2 119.6(4) . . ?
C6 C1 Sb1 120.9(3) . . ?
C2 C1 Sb1 119.4(3) . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 C7 121.1(4) . . ?
C1 C2 C7 118.9(3) . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 C13 121.5(4) . . ?
C1 C6 C13 118.8(3) . . ?
N1 C7 C2 110.7(3) . . ?
N1 C7 H7A 109.5 . . ?
C2 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 C9 111.9(3) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 C8 111.1(3) . . ?
N2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
N1 C10 C11 111.3(3) . . ?
N1 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
N1 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108 . . ?
N2 C11 C10 110.5(3) . . ?
N2 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C6 112.1(3) . . ?
N3 C13 H13A 109.2 . . ?
C6 C13 H13A 109.2 . . ?
N3 C13 H13B 109.2 . . ?
C6 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N3 C14 C15 111.5(3) . . ?
N3 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
N3 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108 . . ?
N4 C15 C14 110.4(3) . . ?
N4 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N4 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N3 C16 C17 111.4(3) . . ?
N3 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N3 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108 . . ?
N4 C17 C16 110.4(3) . . ?
N4 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N4 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 C24 122.5(3) . . ?
O1 C19 C20 117.2(3) . . ?
C24 C19 C20 120.2(4) . . ?
O2 C20 C21 123.4(3) . . ?
O2 C20 C19 117.1(3) . . ?
C21 C20 C19 119.5(3) . . ?
C20 C21 C22 120.7(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 119.0(4) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 120.9(4) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C19 C24 C23 119.5(4) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C10 N1 C7 109.8(3) . . ?
C10 N1 C8 110.1(3) . . ?
C7 N1 C8 109.1(3) . . ?
C11 N2 C9 108.6(3) . . ?
C11 N2 C12 111.9(3) . . ?
C9 N2 C12 111.5(3) . . ?
C13 N3 C16 110.3(3) . . ?
C13 N3 C14 109.5(3) . . ?
C16 N3 C14 110.0(3) . . ?
C17 N4 C15 108.2(3) . . ?
C17 N4 C18 111.7(4) . . ?
C15 N4 C18 111.6(4) . . ?
C19 O1 Sb1 112.5(2) . . ?
C20 O2 Sb1 111.7(2) . . ?
O1 Sb1 O2 78.95(10) . . ?
O1 Sb1 C1 93.82(12) . . ?
O2 Sb1 C1 94.75(12) . . ?

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 -1.7(5) . . . . ?
Sb1 C1 C2 C3 -178.9(3) . . . . ?
C6 C1 C2 C7 176.6(3) . . . . ?
Sb1 C1 C2 C7 -0.6(5) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C7 C2 C3 C4 -178.3(4) . . . . ?
C2 C3 C4 C5 1.6(6) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
C4 C5 C6 C1 -0.2(6) . . . . ?
C4 C5 C6 C13 179.6(4) . . . . ?
C2 C1 C6 C5 1.8(5) . . . . ?
Sb1 C1 C6 C5 179.0(3) . . . . ?
C2 C1 C6 C13 -178.0(3) . . . . ?
Sb1 C1 C6 C13 -0.8(5) . . . . ?
C3 C2 C7 N1 142.0(3) . . . . ?
C1 C2 C7 N1 -36.3(5) . . . . ?
N1 C8 C9 N2 57.1(4) . . . . ?
N1 C10 C11 N2 -58.4(4) . . . . ?
C5 C6 C13 N3 -142.4(4) . . . . ?
C1 C6 C13 N3 37.4(5) . . . . ?
N3 C14 C15 N4 -57.8(4) . . . . ?
N3 C16 C17 N4 58.9(4) . . . . ?
O1 C19 C20 O2 2.3(5) . . . . ?
C24 C19 C20 O2 -176.6(3) . . . . ?
O1 C19 C20 C21 -175.8(3) . . . . ?
C24 C19 C20 C21 5.3(6) . . . . ?
O2 C20 C21 C22 177.5(3) . . . . ?
C19 C20 C21 C22 -4.6(6) . . . . ?
C20 C21 C22 C23 1.2(6) . . . . ?
C21 C22 C23 C24 1.6(6) . . . . ?
O1 C19 C24 C23 178.5(4) . . . . ?
C20 C19 C24 C23 -2.6(6) . . . . ?
C22 C23 C24 C19 -0.8(6) . . . . ?
C11 C10 N1 C7 173.2(3) . . . . ?
C11 C10 N1 C8 53.1(4) . . . . ?
C2 C7 N1 C10 167.2(3) . . . . ?
C2 C7 N1 C8 -72.1(4) . . . . ?
C9 C8 N1 C10 -52.7(4) . . . . ?
C9 C8 N1 C7 -173.3(3) . . . . ?
C10 C11 N2 C9 60.7(4) . . . . ?
C10 C11 N2 C12 -175.8(3) . . . . ?
C8 C9 N2 C11 -60.2(4) . . . . ?
C8 C9 N2 C12 176.0(3) . . . . ?
C6 C13 N3 C16 -166.8(3) . . . . ?
C6 C13 N3 C14 71.9(4) . . . . ?
C17 C16 N3 C13 -174.6(3) . . . . ?
C17 C16 N3 C14 -53.6(4) . . . . ?
C15 C14 N3 C13 174.6(3) . . . . ?
C15 C14 N3 C16 53.2(4) . . . . ?
C16 C17 N4 C15 -61.5(4) . . . . ?
C16 C17 N4 C18 175.2(3) . . . . ?
C14 C15 N4 C17 61.0(4) . . . . ?
C14 C15 N4 C18 -175.7(3) . . . . ?
C24 C19 O1 Sb1 165.4(3) . . . . ?
C20 C19 O1 Sb1 -13.5(4) . . . . ?
C21 C20 O2 Sb1 -172.1(3) . . . . ?
C19 C20 O2 Sb1 9.9(4) . . . . ?

_shelxl_version_number           2014/6



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1041692'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_date             2014-08-25T21:45:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H33 Bi N4 O2'
_chemical_formula_sum            'C24 H33 Bi N4 O2'
_chemical_formula_weight         618.52

#----------------------------------------------------------------------------#
#                   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                   9.8126(9)
_cell_length_b                   10.1505(9)
_cell_length_c                   15.7304(14)
_cell_angle_alpha                82.242(2)
_cell_angle_beta                 77.035(2)
_cell_angle_gamma                64.0120(10)
_cell_volume                     1371.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4079
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      21.02
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    6.452
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.331
_shelx_estimated_absorpt_T_max   0.407

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

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_number            13523
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_number_total             5064
_reflns_number_gt                4282
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0276P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5064
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0742
_refine_ls_wR_factor_gt          0.0675
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.87
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.102

#----------------------------------------------------------------------------#
#                   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'
Bi Bi -4.1077 10.2566 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3394(6) 0.0732(6) 0.6978(3) 0.0494(14) Uani 1 d . .
C2 C 0.3271(6) 0.0870(6) 0.6109(3) 0.0515(14) Uani 1 d . .
C3 C 0.3397(6) -0.0321(7) 0.5714(4) 0.0622(17) Uani 1 d . .
H3 H 0.3338 -0.0251 0.5127 0.075 Uiso 1 calc . .
C4 C 0.3611(7) -0.1625(8) 0.6196(5) 0.0711(18) Uani 1 d . .
H4 H 0.3697 -0.2429 0.5929 0.085 Uiso 1 calc . .
C5 C 0.3696(6) -0.1735(7) 0.7075(4) 0.0636(16) Uani 1 d . .
H5 H 0.3838 -0.2611 0.7395 0.076 Uiso 1 calc . .
C6 C 0.3570(6) -0.0556(6) 0.7469(4) 0.0515(14) Uani 1 d . .
C7 C 0.3015(7) 0.2320(6) 0.5607(4) 0.0608(16) Uani 1 d . .
H7A H 0.3994 0.2389 0.5414 0.073 Uiso 1 calc . .
H7B H 0.2601 0.2365 0.5094 0.073 Uiso 1 calc . .
C8 C 0.0380(6) 0.3625(6) 0.6291(4) 0.0497(13) Uani 1 d . .
H8A H 0.0358 0.2759 0.6629 0.06 Uiso 1 calc . .
H8B H 0.0127 0.3623 0.5729 0.06 Uiso 1 calc . .
C9 C -0.0814(6) 0.4965(6) 0.6755(4) 0.0550(15) Uani 1 d . .
H9A H -0.1828 0.4987 0.6806 0.066 Uiso 1 calc . .
H9B H -0.0626 0.4924 0.734 0.066 Uiso 1 calc . .
C10 C 0.1955(6) 0.4933(6) 0.5715(4) 0.0585(16) Uani 1 d . .
H10A H 0.1773 0.5006 0.5126 0.07 Uiso 1 calc . .
H10B H 0.296 0.4922 0.5677 0.07 Uiso 1 calc . .
C11 C 0.0730(7) 0.6245(7) 0.6208(4) 0.0605(16) Uani 1 d . .
H11A H 0.0948 0.6197 0.6786 0.073 Uiso 1 calc . .
H11B H 0.0758 0.7134 0.5906 0.073 Uiso 1 calc . .
C12 C -0.1976(7) 0.7607(7) 0.6722(4) 0.0763(19) Uani 1 d . .
H12A H -0.1906 0.8466 0.6415 0.114 Uiso 1 calc . .
H12B H -0.1836 0.7572 0.7311 0.114 Uiso 1 calc . .
H12C H -0.2972 0.7643 0.6728 0.114 Uiso 1 calc . .
C13 C 0.3664(6) -0.0622(6) 0.8416(4) 0.0576(15) Uani 1 d . .
H13A H 0.3451 -0.1431 0.8713 0.069 Uiso 1 calc . .
H13B H 0.4705 -0.0812 0.846 0.069 Uiso 1 calc . .
C14 C 0.0984(6) 0.0917(6) 0.8941(4) 0.0522(14) Uani 1 d . .
H14A H 0.089 0.0046 0.923 0.063 Uiso 1 calc . .
H14B H 0.073 0.1031 0.8366 0.063 Uiso 1 calc . .
C15 C -0.0145(6) 0.2238(7) 0.9460(4) 0.0618(16) Uani 1 d . .
H15A H -0.0123 0.3122 0.9147 0.074 Uiso 1 calc . .
H15B H -0.1181 0.2305 0.9529 0.074 Uiso 1 calc . .
C16 C 0.2946(7) 0.0720(7) 0.9701(4) 0.0609(16) Uani 1 d . .
H16A H 0.3963 0.0701 0.9624 0.073 Uiso 1 calc . .
H16B H 0.2961 -0.0158 1.0039 0.073 Uiso 1 calc . .
C17 C 0.1760(7) 0.2070(7) 1.0200(4) 0.0642(16) Uani 1 d . .
H17A H 0.202 0.2034 1.0765 0.077 Uiso 1 calc . .
H17B H 0.1781 0.2949 0.9879 0.077 Uiso 1 calc . .
C18 C -0.0888(9) 0.3330(8) 1.0854(5) 0.099(3) Uani 1 d . .
H18A H -0.0608 0.3215 1.1415 0.148 Uiso 1 calc . .
H18B H -0.1886 0.333 1.0926 0.148 Uiso 1 calc . .
H18C H -0.0919 0.4241 1.0575 0.148 Uiso 1 calc . .
C19 C 0.6289(6) 0.2176(6) 0.6726(4) 0.0535(14) Uani 1 d . .
C20 C 0.6499(6) 0.1392(6) 0.7533(3) 0.0479(13) Uani 1 d . .
C21 C 0.7985(6) 0.0542(6) 0.7676(4) 0.0572(15) Uani 1 d . .
H21 H 0.8143 0.0084 0.8222 0.069 Uiso 1 calc . .
C22 C 0.9241(7) 0.0367(7) 0.7011(4) 0.0672(17) Uani 1 d . .
H22 H 1.0238 -0.022 0.7106 0.081 Uiso 1 calc . .
C23 C 0.9004(7) 0.1068(7) 0.6206(4) 0.0664(17) Uani 1 d . .
H23 H 0.9841 0.0926 0.5753 0.08 Uiso 1 calc . .
C24 C 0.7545(7) 0.1971(7) 0.6073(4) 0.0598(16) Uani 1 d . .
H24 H 0.7401 0.2453 0.5532 0.072 Uiso 1 calc . .
N1 N 0.1945(4) 0.3551(5) 0.6154(3) 0.0454(11) Uani 1 d . .
N2 N -0.0785(5) 0.6306(5) 0.6286(3) 0.0542(12) Uani 1 d . .
N3 N 0.2590(5) 0.0722(5) 0.8847(3) 0.0470(11) Uani 1 d . .
N4 N 0.0243(6) 0.2127(5) 1.0319(3) 0.0628(13) Uani 1 d . .
O1 O 0.4829(4) 0.3092(5) 0.6617(2) 0.0675(12) Uani 1 d . .
O2 O 0.5234(4) 0.1542(4) 0.8149(2) 0.0544(10) Uani 1 d . .
Bi1 Bi 0.31101(2) 0.27036(2) 0.76188(2) 0.04690(9) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.382(7) . ?
C1 C6 1.387(7) . ?
C1 Bi1 2.242(6) . ?
C2 C3 1.379(8) . ?
C2 C7 1.518(8) . ?
C3 C4 1.388(9) . ?
C3 H3 0.93 . ?
C4 C5 1.392(9) . ?
C4 H4 0.93 . ?
C5 C6 1.367(8) . ?
C5 H5 0.93 . ?
C6 C13 1.503(8) . ?
C7 N1 1.463(7) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 N1 1.472(6) . ?
C8 C9 1.498(7) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N2 1.466(7) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 N1 1.480(7) . ?
C10 C11 1.510(8) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N2 1.439(7) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 N2 1.454(7) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 N3 1.449(7) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 N3 1.474(6) . ?
C14 C15 1.510(8) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 N4 1.460(7) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 N3 1.462(7) . ?
C16 C17 1.527(8) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 N4 1.435(7) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 N4 1.450(8) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 O1 1.358(6) . ?
C19 C24 1.372(7) . ?
C19 C20 1.410(7) . ?
C20 O2 1.356(6) . ?
C20 C21 1.384(7) . ?
C21 C22 1.388(8) . ?
C21 H21 0.93 . ?
C22 C23 1.381(9) . ?
C22 H22 0.93 . ?
C23 C24 1.366(8) . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
N1 Bi1 2.672(4) . ?
N3 Bi1 2.729(4) . ?
O1 Bi1 2.169(3) . ?
O2 Bi1 2.189(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.3(5) . . ?
C2 C1 Bi1 118.5(4) . . ?
C6 C1 Bi1 120.0(4) . . ?
C3 C2 C1 119.1(6) . . ?
C3 C2 C7 121.3(5) . . ?
C1 C2 C7 119.5(5) . . ?
C2 C3 C4 119.9(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.3(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.0(6) . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
C5 C6 C1 119.3(5) . . ?
C5 C6 C13 122.0(6) . . ?
C1 C6 C13 118.6(5) . . ?
N1 C7 C2 110.6(4) . . ?
N1 C7 H7A 109.5 . . ?
C2 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 C9 112.5(4) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N2 C9 C8 111.2(4) . . ?
N2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
N1 C10 C11 110.9(4) . . ?
N1 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108 . . ?
N2 C11 C10 111.6(5) . . ?
N2 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C6 112.6(4) . . ?
N3 C13 H13A 109.1 . . ?
C6 C13 H13A 109.1 . . ?
N3 C13 H13B 109.1 . . ?
C6 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
N3 C14 C15 112.0(5) . . ?
N3 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N4 C15 C14 110.5(5) . . ?
N4 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N3 C16 C17 111.5(5) . . ?
N3 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N3 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108 . . ?
N4 C17 C16 110.4(5) . . ?
N4 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N4 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 C24 122.2(5) . . ?
O1 C19 C20 118.2(5) . . ?
C24 C19 C20 119.6(5) . . ?
O2 C20 C21 122.5(5) . . ?
O2 C20 C19 118.6(5) . . ?
C21 C20 C19 118.8(5) . . ?
C20 C21 C22 120.4(6) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.7(6) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C24 C23 C22 120.3(6) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C19 120.9(6) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C7 N1 C8 109.3(4) . . ?
C7 N1 C10 109.3(4) . . ?
C8 N1 C10 109.6(4) . . ?
C7 N1 Bi1 100.3(3) . . ?
C8 N1 Bi1 111.6(3) . . ?
C10 N1 Bi1 116.2(3) . . ?
C11 N2 C12 111.8(5) . . ?
C11 N2 C9 108.6(4) . . ?
C12 N2 C9 111.2(5) . . ?
C13 N3 C16 110.2(4) . . ?
C13 N3 C14 111.1(4) . . ?
C16 N3 C14 110.3(4) . . ?
C13 N3 Bi1 99.2(3) . . ?
C16 N3 Bi1 116.0(3) . . ?
C14 N3 Bi1 109.6(3) . . ?
C17 N4 C18 111.6(6) . . ?
C17 N4 C15 108.5(4) . . ?
C18 N4 C15 111.6(5) . . ?
C19 O1 Bi1 112.1(3) . . ?
C20 O2 Bi1 111.6(3) . . ?
O1 Bi1 O2 76.62(13) . . ?
O1 Bi1 C1 93.19(17) . . ?
O2 Bi1 C1 94.17(17) . . ?
O1 Bi1 N1 72.89(13) . . ?
O2 Bi1 N1 144.66(12) . . ?
C1 Bi1 N1 70.40(16) . . ?
O1 Bi1 N3 144.69(14) . . ?
O2 Bi1 N3 74.26(13) . . ?
C1 Bi1 N3 69.66(16) . . ?
N1 Bi1 N3 124.82(13) . . ?

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 -2.9(8) . . . . ?
Bi1 C1 C2 C3 -178.1(4) . . . . ?
C6 C1 C2 C7 177.6(5) . . . . ?
Bi1 C1 C2 C7 2.5(6) . . . . ?
C1 C2 C3 C4 1.3(8) . . . . ?
C7 C2 C3 C4 -179.2(5) . . . . ?
C2 C3 C4 C5 0.1(9) . . . . ?
C3 C4 C5 C6 -0.1(9) . . . . ?
C4 C5 C6 C1 -1.5(8) . . . . ?
C4 C5 C6 C13 -179.6(5) . . . . ?
C2 C1 C6 C5 3.0(8) . . . . ?
Bi1 C1 C6 C5 178.1(4) . . . . ?
C2 C1 C6 C13 -178.8(5) . . . . ?
Bi1 C1 C6 C13 -3.7(6) . . . . ?
C3 C2 C7 N1 141.2(5) . . . . ?
C1 C2 C7 N1 -39.3(7) . . . . ?
N1 C8 C9 N2 56.5(6) . . . . ?
N1 C10 C11 N2 -58.8(6) . . . . ?
C5 C6 C13 N3 -141.3(5) . . . . ?
C1 C6 C13 N3 40.5(7) . . . . ?
N3 C14 C15 N4 -56.7(6) . . . . ?
N3 C16 C17 N4 58.7(6) . . . . ?
O1 C19 C20 O2 2.6(8) . . . . ?
C24 C19 C20 O2 -175.9(5) . . . . ?
O1 C19 C20 C21 -175.2(5) . . . . ?
C24 C19 C20 C21 6.3(8) . . . . ?
O2 C20 C21 C22 176.9(5) . . . . ?
C19 C20 C21 C22 -5.4(8) . . . . ?
C20 C21 C22 C23 1.2(9) . . . . ?
C21 C22 C23 C24 2.2(9) . . . . ?
C22 C23 C24 C19 -1.3(9) . . . . ?
O1 C19 C24 C23 178.5(5) . . . . ?
C20 C19 C24 C23 -3.0(9) . . . . ?
C2 C7 N1 C8 -71.1(6) . . . . ?
C2 C7 N1 C10 168.9(5) . . . . ?
C2 C7 N1 Bi1 46.3(5) . . . . ?
C9 C8 N1 C7 -173.1(5) . . . . ?
C9 C8 N1 C10 -53.2(6) . . . . ?
C9 C8 N1 Bi1 76.9(5) . . . . ?
C11 C10 N1 C7 173.3(5) . . . . ?
C11 C10 N1 C8 53.5(6) . . . . ?
C11 C10 N1 Bi1 -74.1(5) . . . . ?
C10 C11 N2 C12 -177.1(5) . . . . ?
C10 C11 N2 C9 59.8(6) . . . . ?
C8 C9 N2 C11 -58.3(6) . . . . ?
C8 C9 N2 C12 178.2(5) . . . . ?
C6 C13 N3 C16 -168.2(5) . . . . ?
C6 C13 N3 C14 69.3(6) . . . . ?
C6 C13 N3 Bi1 -46.0(5) . . . . ?
C17 C16 N3 C13 -175.7(5) . . . . ?
C17 C16 N3 C14 -52.7(6) . . . . ?
C17 C16 N3 Bi1 72.6(5) . . . . ?
C15 C14 N3 C13 174.8(5) . . . . ?
C15 C14 N3 C16 52.3(6) . . . . ?
C15 C14 N3 Bi1 -76.5(5) . . . . ?
C16 C17 N4 C18 175.2(5) . . . . ?
C16 C17 N4 C15 -61.4(6) . . . . ?
C14 C15 N4 C17 60.7(6) . . . . ?
C14 C15 N4 C18 -175.9(5) . . . . ?
C24 C19 O1 Bi1 164.0(4) . . . . ?
C20 C19 O1 Bi1 -14.5(6) . . . . ?
C21 C20 O2 Bi1 -171.7(4) . . . . ?
C19 C20 O2 Bi1 10.5(6) . . . . ?

_shelxl_version_number           2013-3



