# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2d
_database_code_depnum_ccdc_archive 'CCDC 1515224'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H23 Fe N2 O4 Sb'
_chemical_formula_sum            'C20 H23 Fe N2 O4 Sb'
_chemical_formula_weight         533.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   10.9560(8)
_cell_length_b                   9.9450(4)
_cell_length_c                   19.8771(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.737(5)
_cell_angle_gamma                90
_cell_volume                     2150.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    16213
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    1.957
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.197
0 0 1 0.196
0 1 0 0.199
0 -1 0 0.200
-1 0 0 0.202
1 0 0 0.171
0 -1 -1 0.191
-1 0 1 0.241
1 0 1 0.185
1 0 -1 0.183
-1 0 -1 0.187


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.498
_exptl_absorpt_correction_T_max  0.571
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;


_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16165
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         27.13
_reflns_number_total             4662
_reflns_number_gt                4290
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0164P)²+1.5923P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4662
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0196
_refine_ls_wR_factor_ref         0.0492
_refine_ls_wR_factor_gt          0.0459
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.762924(11) 0.108748(12) 0.913369(6) 0.01768(4) Uani 1 1 d . . .
Fe1 Fe 0.81393(2) 0.31004(3) 0.837875(13) 0.01768(6) Uani 1 1 d . . .
C1 C 0.57968(17) 0.13871(18) 0.93017(9) 0.0177(3) Uani 1 1 d . . .
C9 C 0.8550(3) 0.4300(3) 1.08621(15) 0.0507(7) Uani 1 1 d . . .
H9A H 0.8262 0.4840 1.0475 0.061 Uiso 1 1 d R . .
H9B H 0.9313 0.4659 1.1075 0.061 Uiso 1 1 d R . .
H9C H 0.7952 0.4309 1.1178 0.061 Uiso 1 1 d R . .
O2 O 1.06485(14) 0.20298(18) 0.86429(8) 0.0347(4) Uani 1 1 d . . .
N1 N 0.76602(16) 0.23917(17) 1.01654(8) 0.0223(3) Uani 1 1 d . . .
C17 C 0.71453(18) 0.24963(19) 0.76812(10) 0.0228(4) Uani 1 1 d . . .
O1 O 0.65082(14) 0.22120(16) 0.71962(7) 0.0317(3) Uani 1 1 d . . .
C3 C 0.4309(2) 0.2265(2) 0.99933(10) 0.0276(4) Uani 1 1 d . . .
H3 H 0.4124 0.2754 1.0367 0.033 Uiso 1 1 d R . .
C20 C 0.86729(19) 0.4460(2) 0.79206(10) 0.0246(4) Uani 1 1 d . . .
N2 N 0.63643(15) -0.01513(15) 0.82623(8) 0.0200(3) Uani 1 1 d . . .
O4 O 0.90299(16) 0.53328(17) 0.76248(9) 0.0411(4) Uani 1 1 d . . .
C5 C 0.36305(19) 0.0962(2) 0.89978(11) 0.0243(4) Uani 1 1 d . . .
H5 H 0.2996 0.0576 0.8710 0.029 Uiso 1 1 d R . .
C12 C 0.52196(18) -0.00291(18) 0.83247(10) 0.0215(4) Uani 1 1 d . . .
H12 H 0.4631 -0.0459 0.8024 0.026 Uiso 1 1 d R . .
C4 C 0.33705(19) 0.1705(2) 0.95545(11) 0.0279(4) Uani 1 1 d . . .
H4 H 0.2558 0.1826 0.9634 0.033 Uiso 1 1 d R . .
C18 C 0.96663(19) 0.2440(2) 0.85435(10) 0.0232(4) Uani 1 1 d . . .
C7 C 0.6580(2) 0.2594(2) 1.03171(10) 0.0256(4) Uani 1 1 d . . .
H7 H 0.6462 0.3052 1.0712 0.031 Uiso 1 1 d R . .
O3 O 0.68512(19) 0.49012(17) 0.92246(9) 0.0472(5) Uani 1 1 d . . .
C19 C 0.7375(2) 0.4170(2) 0.89148(11) 0.0287(4) Uani 1 1 d . . .
C15 C 0.5987(2) -0.1047(2) 0.70786(11) 0.0323(5) Uani 1 1 d . . .
H15A H 0.5172 -0.1356 0.7127 0.039 Uiso 1 1 d R . .
H15B H 0.6339 -0.1604 0.6757 0.039 Uiso 1 1 d R . .
H15C H 0.5952 -0.0134 0.6922 0.039 Uiso 1 1 d R . .
C2 C 0.55299(18) 0.21000(19) 0.98703(9) 0.0216(4) Uani 1 1 d . . .
C13 C 0.6781(2) -0.11242(19) 0.77616(11) 0.0256(4) Uani 1 1 d . . .
C6 C 0.48536(17) 0.07986(18) 0.88718(9) 0.0191(4) Uani 1 1 d . . .
C8 C 0.8750(2) 0.2853(2) 1.06355(10) 0.0290(4) Uani 1 1 d . . .
C16 C 0.8109(2) -0.0792(2) 0.76743(12) 0.0328(5) Uani 1 1 d . . .
H16A H 0.8145 0.0081 0.7471 0.039 Uiso 1 1 d R . .
H16B H 0.8423 -0.1453 0.7387 0.039 Uiso 1 1 d R . .
H16C H 0.8596 -0.0793 0.8108 0.039 Uiso 1 1 d R . .
C10 C 0.8891(2) 0.1911(3) 1.12436(12) 0.0424(6) Uani 1 1 d . . .
H10A H 0.8157 0.1941 1.1464 0.051 Uiso 1 1 d R . .
H10B H 0.9579 0.2190 1.1556 0.051 Uiso 1 1 d R . .
H10C H 0.9023 0.1010 1.1095 0.051 Uiso 1 1 d R . .
C14 C 0.6710(2) -0.2526(2) 0.80700(13) 0.0375(5) Uani 1 1 d . . .
H14A H 0.7181 -0.2544 0.8509 0.045 Uiso 1 1 d R . .
H14B H 0.7035 -0.3175 0.7781 0.045 Uiso 1 1 d R . .
H14C H 0.5868 -0.2739 0.8113 0.045 Uiso 1 1 d R . .
C11 C 0.9878(2) 0.2777(3) 1.02665(12) 0.0465(7) Uani 1 1 d . . .
H11A H 0.9972 0.1874 1.0110 0.056 Uiso 1 1 d R . .
H11B H 1.0589 0.3024 1.0570 0.056 Uiso 1 1 d R . .
H11C H 0.9791 0.3380 0.9887 0.056 Uiso 1 1 d R . .


_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
Sb1 C1 2.0947(19) . ?
Sb1 N1 2.4234(16) . ?
Sb1 N2 2.4238(16) . ?
Sb1 Fe1 2.6015(3) . ?
Fe1 C17 1.765(2) . ?
Fe1 C20 1.768(2) . ?
Fe1 C19 1.782(2) . ?
Fe1 C18 1.791(2) . ?
C1 C6 1.390(3) . ?
C1 C2 1.394(3) . ?
C9 C8 1.532(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O2 C18 1.146(3) . ?
N1 C7 1.271(3) . ?
N1 C8 1.499(3) . ?
C17 O1 1.157(3) . ?
C3 C4 1.385(3) . ?
C3 C2 1.397(3) . ?
C3 H3 0.9301 . ?
C20 O4 1.142(3) . ?
N2 C12 1.280(3) . ?
N2 C13 1.497(2) . ?
C5 C4 1.388(3) . ?
C5 C6 1.401(3) . ?
C5 H5 0.9300 . ?
C12 C6 1.457(3) . ?
C12 H12 0.9300 . ?
C4 H4 0.9300 . ?
C7 C2 1.454(3) . ?
C7 H7 0.9299 . ?
O3 C19 1.149(3) . ?
C15 C13 1.526(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9599 . ?
C15 H15C 0.9600 . ?
C13 C16 1.521(3) . ?
C13 C14 1.528(3) . ?
C8 C11 1.511(3) . ?
C8 C10 1.523(3) . ?
C16 H16A 0.9601 . ?
C16 H16B 0.9601 . ?
C16 H16C 0.9599 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C14 H14A 0.9599 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9599 . ?

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
C1 Sb1 N1 72.99(7) . . ?
C1 Sb1 N2 73.02(6) . . ?
N1 Sb1 N2 145.77(6) . . ?
C1 Sb1 Fe1 104.90(5) . . ?
N1 Sb1 Fe1 95.37(4) . . ?
N2 Sb1 Fe1 97.03(4) . . ?
C17 Fe1 C20 93.82(9) . . ?
C17 Fe1 C19 112.51(10) . . ?
C20 Fe1 C19 93.35(9) . . ?
C17 Fe1 C18 119.72(9) . . ?
C20 Fe1 C18 90.94(9) . . ?
C19 Fe1 C18 127.13(10) . . ?
C17 Fe1 Sb1 92.11(6) . . ?
C20 Fe1 Sb1 172.84(7) . . ?
C19 Fe1 Sb1 88.08(7) . . ?
C18 Fe1 Sb1 82.62(6) . . ?
C6 C1 C2 120.06(17) . . ?
C6 C1 Sb1 119.95(13) . . ?
C2 C1 Sb1 119.85(14) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 N1 C8 119.97(17) . . ?
C7 N1 Sb1 111.37(13) . . ?
C8 N1 Sb1 128.47(13) . . ?
O1 C17 Fe1 173.77(18) . . ?
C4 C3 C2 119.84(19) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 120.3 . . ?
O4 C20 Fe1 179.26(19) . . ?
C12 N2 C13 120.27(16) . . ?
C12 N2 Sb1 111.54(12) . . ?
C13 N2 Sb1 127.59(12) . . ?
C4 C5 C6 119.62(19) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.3 . . ?
N2 C12 C6 118.96(17) . . ?
N2 C12 H12 120.5 . . ?
C6 C12 H12 120.5 . . ?
C3 C4 C5 120.64(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
O2 C18 Fe1 179.07(19) . . ?
N1 C7 C2 119.59(18) . . ?
N1 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
O3 C19 Fe1 175.7(2) . . ?
C13 C15 H15A 109.6 . . ?
C13 C15 H15B 109.4 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C2 C3 119.87(18) . . ?
C1 C2 C7 116.15(17) . . ?
C3 C2 C7 123.95(18) . . ?
N2 C13 C16 107.80(16) . . ?
N2 C13 C15 111.88(17) . . ?
C16 C13 C15 109.91(18) . . ?
N2 C13 C14 106.80(17) . . ?
C16 C13 C14 109.76(19) . . ?
C15 C13 C14 110.60(18) . . ?
C1 C6 C5 119.92(18) . . ?
C1 C6 C12 116.53(17) . . ?
C5 C6 C12 123.47(18) . . ?
N1 C8 C11 108.61(17) . . ?
N1 C8 C10 107.78(18) . . ?
C11 C8 C10 110.0(2) . . ?
N1 C8 C9 109.87(19) . . ?
C11 C8 C9 110.1(2) . . ?
C10 C8 C9 110.4(2) . . ?
C13 C16 H16A 109.4 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.6 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C10 H10A 109.3 . . ?
C8 C10 H10B 109.6 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.6 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.4 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C11 H11A 109.3 . . ?
C8 C11 H11B 109.3 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.8 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.13
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_3d
_database_code_depnum_ccdc_archive 'CCDC 1515225'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H23 Bi Fe N2 O4'
_chemical_formula_sum            'C20 H23 Bi Fe N2 O4'
_chemical_formula_weight         620.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Fe Fe 0.3463 0.8444 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   11.1360(10)
_cell_length_b                   11.5650(10)
_cell_length_c                   18.6181(13)
_cell_angle_alpha                90
_cell_angle_beta                 112.958(6)
_cell_angle_gamma                90
_cell_volume                     2207.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    21187
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    8.643
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.097
0 -1 -1 0.111
0 0 1 0.056
-1 0 0 0.085
1 0 0 0.127
0 0 -1 0.145
1 1 1 0.104
1 -1 -1 0.129


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.222
_exptl_absorpt_correction_T_max  0.326
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21097
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4989
_reflns_number_gt                4132
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0328P)²+7.9776P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4989
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.639608(18) 0.357134(17) 0.171392(11) 0.02360(8) Uani 1 1 d . . .
Fe1 Fe 0.67922(7) 0.14613(7) 0.23466(4) 0.02601(17) Uani 1 1 d . . .
C4 C 0.9193(6) 0.3386(5) 0.0183(3) 0.0333(13) Uani 1 1 d . . .
H4 H 0.9717 0.3340 -0.0102 0.040 Uiso 1 1 d R . .
O3 O 0.9555(4) 0.1921(4) 0.3257(3) 0.0428(11) Uani 1 1 d . . .
C5 C 0.9704(5) 0.3791(5) 0.0943(3) 0.0303(12) Uani 1 1 d . . .
H5 H 1.0568 0.4033 0.1163 0.036 Uiso 1 1 d R . .
C6 C 0.8942(5) 0.3830(5) 0.1386(3) 0.0266(11) Uani 1 1 d . . .
C1 C 0.7650(5) 0.3436(5) 0.1056(3) 0.0248(11) Uani 1 1 d . . .
C10 C 0.3210(6) 0.1860(6) 0.0398(4) 0.0425(16) Uani 1 1 d . . .
H10A H 0.3594 0.1150 0.0325 0.051 Uiso 1 1 d R . .
H10B H 0.2278 0.1779 0.0196 0.051 Uiso 1 1 d R . .
H10C H 0.3528 0.2039 0.0945 0.051 Uiso 1 1 d R . .
N1 N 0.5025(4) 0.2941(4) 0.0331(2) 0.0230(9) Uani 1 1 d . . .
N2 N 0.8632(4) 0.4440(4) 0.2520(3) 0.0281(10) Uani 1 1 d . . .
C19 C 0.8464(6) 0.1784(5) 0.2888(3) 0.0306(12) Uani 1 1 d . . .
C7 C 0.5720(5) 0.2822(5) -0.0073(3) 0.0282(11) Uani 1 1 d . . .
H7 H 0.5339 0.2595 -0.0593 0.034 Uiso 1 1 d R . .
O2 O 0.6246(5) 0.0490(4) 0.0798(3) 0.0533(13) Uani 1 1 d . . .
C12 C 0.9397(5) 0.4356(5) 0.2161(3) 0.0281(11) Uani 1 1 d . . .
H12 H 1.0250 0.4624 0.2397 0.034 Uiso 1 1 d R . .
C2 C 0.7125(5) 0.3057(5) 0.0285(3) 0.0253(11) Uani 1 1 d . . .
C8 C 0.3574(5) 0.2824(5) -0.0024(3) 0.0273(11) Uani 1 1 d . . .
C16 C 0.8365(7) 0.6297(5) 0.3028(4) 0.0428(16) Uani 1 1 d . . .
H16A H 0.8714 0.6659 0.2687 0.051 Uiso 1 1 d R . .
H16B H 0.8567 0.6760 0.3489 0.051 Uiso 1 1 d R . .
H16C H 0.7436 0.6226 0.2765 0.051 Uiso 1 1 d R . .
C3 C 0.7899(5) 0.3034(5) -0.0151(3) 0.0294(12) Uani 1 1 d . . .
H3 H 0.7534 0.2798 -0.0669 0.035 Uiso 1 1 d R . .
C13 C 0.8970(6) 0.5102(5) 0.3255(3) 0.0291(12) Uani 1 1 d . . .
C18 C 0.6444(6) 0.0905(5) 0.1390(4) 0.0352(13) Uani 1 1 d . . .
C17 C 0.6871(6) 0.0064(6) 0.2730(4) 0.0449(16) Uani 1 1 d . . .
C15 C 1.0454(7) 0.5245(7) 0.3703(4) 0.0499(18) Uani 1 1 d . . .
H15A H 1.0857 0.4498 0.3826 0.060 Uiso 1 1 d R . .
H15B H 1.0621 0.5667 0.4177 0.060 Uiso 1 1 d R . .
H15C H 1.0807 0.5662 0.3384 0.060 Uiso 1 1 d R . .
C20 C 0.5613(6) 0.1898(6) 0.2717(3) 0.0379(14) Uani 1 1 d . . .
O1 O 0.6907(5) -0.0858(5) 0.2969(4) 0.0688(17) Uani 1 1 d . . .
C11 C 0.3046(6) 0.2573(7) -0.0896(3) 0.0433(16) Uani 1 1 d . . .
H11A H 0.3305 0.3184 -0.1155 0.052 Uiso 1 1 d R . .
H11B H 0.2111 0.2532 -0.1097 0.052 Uiso 1 1 d R . .
H11C H 0.3389 0.1852 -0.0987 0.052 Uiso 1 1 d R . .
O4 O 0.4878(5) 0.2155(6) 0.2985(3) 0.0618(16) Uani 1 1 d . . .
C9 C 0.3036(7) 0.3965(7) 0.0122(5) 0.055(2) Uani 1 1 d . . .
H9A H 0.3264 0.4056 0.0672 0.066 Uiso 1 1 d R . .
H9B H 0.2103 0.3964 -0.0144 0.066 Uiso 1 1 d R . .
H9C H 0.3395 0.4593 -0.0067 0.066 Uiso 1 1 d R . .
C14 C 0.8378(9) 0.4491(7) 0.3750(4) 0.058(2) Uani 1 1 d . . .
H14A H 0.7445 0.4483 0.3489 0.070 Uiso 1 1 d R . .
H14B H 0.8620 0.4884 0.4241 0.070 Uiso 1 1 d R . .
H14C H 0.8697 0.3711 0.3839 0.070 Uiso 1 1 d R . .


_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
Bi1 C1 2.194(5) . ?
Bi1 N1 2.534(4) . ?
Bi1 N2 2.558(4) . ?
Bi1 Fe1 2.6706(8) . ?
Fe1 C17 1.755(7) . ?
Fe1 C19 1.776(6) . ?
Fe1 C20 1.778(6) . ?
Fe1 C18 1.789(6) . ?
C4 C5 1.386(8) . ?
C4 C3 1.390(8) . ?
C4 H4 0.9299 . ?
O3 C19 1.150(7) . ?
C5 C6 1.395(7) . ?
C5 H5 0.9299 . ?
C6 C1 1.402(8) . ?
C6 C12 1.463(8) . ?
C1 C2 1.393(7) . ?
C10 C8 1.508(8) . ?
C10 H10A 0.9601 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9599 . ?
N1 C7 1.281(7) . ?
N1 C8 1.495(6) . ?
N2 C12 1.276(7) . ?
N2 C13 1.483(7) . ?
C7 C2 1.467(7) . ?
C7 H7 0.9300 . ?
O2 C18 1.141(8) . ?
C12 H12 0.9300 . ?
C2 C3 1.395(7) . ?
C8 C9 1.517(9) . ?
C8 C11 1.523(8) . ?
C16 C13 1.523(8) . ?
C16 H16A 0.9599 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C3 H3 0.9299 . ?
C13 C14 1.502(8) . ?
C13 C15 1.542(9) . ?
C17 O1 1.150(8) . ?
C15 H15A 0.9601 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C20 O4 1.151(8) . ?
C11 H11A 0.9601 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9601 . ?
C9 H9A 0.9599 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9601 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C1 Bi1 N1 71.00(17) . . ?
C1 Bi1 N2 70.72(17) . . ?
N1 Bi1 N2 140.50(14) . . ?
C1 Bi1 Fe1 98.60(14) . . ?
N1 Bi1 Fe1 96.64(10) . . ?
N2 Bi1 Fe1 98.31(11) . . ?
C17 Fe1 C19 95.0(3) . . ?
C17 Fe1 C20 91.8(3) . . ?
C19 Fe1 C20 119.3(3) . . ?
C17 Fe1 C18 91.7(3) . . ?
C19 Fe1 C18 114.4(3) . . ?
C20 Fe1 C18 125.6(3) . . ?
C17 Fe1 Bi1 173.9(2) . . ?
C19 Fe1 Bi1 90.83(19) . . ?
C20 Fe1 Bi1 83.8(2) . . ?
C18 Fe1 Bi1 87.43(19) . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.8(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.1(5) . . ?
C5 C6 C12 122.7(5) . . ?
C1 C6 C12 118.0(5) . . ?
C2 C1 C6 120.1(5) . . ?
C2 C1 Bi1 119.7(4) . . ?
C6 C1 Bi1 120.0(4) . . ?
C8 C10 H10A 109.4 . . ?
C8 C10 H10B 109.7 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.3 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 N1 C8 121.8(5) . . ?
C7 N1 Bi1 111.5(3) . . ?
C8 N1 Bi1 126.5(3) . . ?
C12 N2 C13 122.8(5) . . ?
C12 N2 Bi1 111.0(4) . . ?
C13 N2 Bi1 125.7(3) . . ?
O3 C19 Fe1 175.6(6) . . ?
N1 C7 C2 119.7(5) . . ?
N1 C7 H7 120.4 . . ?
C2 C7 H7 119.9 . . ?
N2 C12 C6 120.2(5) . . ?
N2 C12 H12 119.6 . . ?
C6 C12 H12 120.1 . . ?
C1 C2 C3 120.0(5) . . ?
C1 C2 C7 118.1(5) . . ?
C3 C2 C7 121.6(5) . . ?
N1 C8 C10 107.5(4) . . ?
N1 C8 C9 106.1(5) . . ?
C10 C8 C9 110.1(6) . . ?
N1 C8 C11 113.0(4) . . ?
C10 C8 C11 110.2(5) . . ?
C9 C8 C11 109.9(6) . . ?
C13 C16 H16A 109.3 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.6 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 119.4 . . ?
N2 C13 C14 108.0(5) . . ?
N2 C13 C16 106.7(5) . . ?
C14 C13 C16 110.2(6) . . ?
N2 C13 C15 112.8(5) . . ?
C14 C13 C15 110.7(6) . . ?
C16 C13 C15 108.5(5) . . ?
O2 C18 Fe1 176.1(5) . . ?
O1 C17 Fe1 178.8(7) . . ?
C13 C15 H15A 109.6 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.3 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C20 Fe1 177.1(6) . . ?
C8 C11 H11A 109.1 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.8 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 110.0 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C13 C14 H14A 109.9 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.1 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         2.338
_refine_diff_density_min         -1.510
_refine_diff_density_rms         0.160
####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1515226'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_CHEMW03_2a                  
;
PROBLEM: WARNING: The ratio of given/expected molecular ...  
RESPONSE: The structure contains disordered toluene.
The Platon SQUEEZE program was used.
;
_vrf_CELLZ01_2a                  
;
PROBLEM: WARNING:  Difference between formula and atom_site ...  
RESPONSE: The structure contains disordered toluene.
The Platon SQUEEZE program was used.
;
_vrf_FORMU01_2a                  
;
PROBLEM: There is a discrepancy between the atom ...  
RESPONSE: The structure contains disordered toluene.
The Platon SQUEEZE program was used.
;
_vrf_PLAT041_2a                  
;
PROBLEM: WARNING:  Calc. and Reported SumFormula ...  
RESPONSE: The structure contains disordered toluene.
The Platon SQUEEZE program was used.
;
_vrf_PLAT990_2a                  
;
PROBLEM: Depricated RES file style based SQUEEZE job ...  
RESPONSE: The structure contains disordered toluene.
The Platon SQUEEZE program was used.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 Cr N2 O5 Sb, 0.5(C7 H8)'
_chemical_formula_sum            'C24.50 H27 Cr N2 O5 Sb'
_chemical_formula_weight         603.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Cr Cr 0.3209 0.6236 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   28.4024(6)
_cell_length_b                   9.3490(2)
_cell_length_c                   19.5303(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.652(4)
_cell_angle_gamma                90
_cell_volume                     5160.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    20114
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             2424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.504
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.137
0 -1 0 0.147
-1 0 0 0.025
1 0 0 0.025
0 0 -1 0.113
0 0 1 0.047
0 -1 1 0.127


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_reflns_number            20016
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.424
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5807
_reflns_number_gt                4502
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0131P)²+11.2245P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5807
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0601
_refine_ls_wR_factor_gt          0.0528
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.14438(2) 0.49756(2) 0.17660(2) 0.01986(5) Uani 1 1 d . . . . .
Cr1 Cr 0.07489(2) 0.70305(4) 0.16995(2) 0.02028(9) Uani 1 1 d . . . . .
C12 C 0.07909(10) 0.2281(3) 0.15616(14) 0.0274(6) Uani 1 1 d . . . . .
H12 H 0.0600 0.1526 0.1394 0.033 Uiso 1 1 d R U . . .
C1 C 0.11970(9) 0.3613(3) 0.24995(13) 0.0201(5) Uani 1 1 d . . . . .
C18 C 0.07901(9) 0.6978(3) 0.26790(14) 0.0248(6) Uani 1 1 d . . . . .
N2 N 0.09686(8) 0.3132(2) 0.11416(10) 0.0229(5) Uani 1 1 d . . . . .
O3 O 0.00142(7) 0.4642(2) 0.16472(11) 0.0374(5) Uani 1 1 d . . . . .
N1 N 0.18347(7) 0.5694(2) 0.28775(11) 0.0223(5) Uani 1 1 d . . . . .
O4 O 0.07629(8) 0.7326(3) 0.01638(11) 0.0458(6) Uani 1 1 d . . . . .
O2 O 0.08144(7) 0.6974(2) 0.32661(10) 0.0359(5) Uani 1 1 d . . . . .
O1 O -0.00172(7) 0.9235(2) 0.15787(11) 0.0375(5) Uani 1 1 d . . . . .
O5 O 0.14417(7) 0.9459(2) 0.17222(12) 0.0436(6) Uani 1 1 d . . . . .
C14 C 0.04233(12) 0.3519(4) 0.01170(17) 0.0520(9) Uani 1 1 d . . . . .
H14A H 0.0176 0.3068 0.0340 0.062 Uiso 1 1 d R U . . .
H14B H 0.0370 0.3363 -0.0370 0.062 Uiso 1 1 d R U . . .
H14C H 0.0423 0.4527 0.0210 0.062 Uiso 1 1 d R U . . .
C17 C 0.02752(10) 0.8376(3) 0.16396(14) 0.0259(6) Uani 1 1 d . . . . .
C21 C 0.11963(10) 0.8515(3) 0.17337(15) 0.0289(6) Uani 1 1 d . . . . .
C6 C 0.08911(9) 0.2493(3) 0.22966(13) 0.0243(6) Uani 1 1 d . . . . .
C2 C 0.13517(9) 0.3796(3) 0.31950(13) 0.0240(6) Uani 1 1 d . . . . .
C3 C 0.11824(11) 0.2892(3) 0.36877(14) 0.0337(7) Uani 1 1 d . . . . .
H3 H 0.1285 0.3011 0.4151 0.040 Uiso 1 1 d R U . . .
C20 C 0.07568(10) 0.7132(3) 0.07420(15) 0.0286(6) Uani 1 1 d . . . . .
C7 C 0.17038(9) 0.4899(3) 0.33618(13) 0.0256(5) Uani 1 1 d . . . . .
H7 H 0.1832 0.5036 0.3814 0.031 Uiso 1 1 d R U . . .
C4 C 0.08644(11) 0.1825(3) 0.34817(15) 0.0377(7) Uani 1 1 d . . . . .
H4 H 0.0741 0.1255 0.3811 0.045 Uiso 1 1 d R U . . .
C19 C 0.02945(10) 0.5512(3) 0.16620(14) 0.0261(6) Uani 1 1 d . . . . .
C13 C 0.08916(11) 0.2879(3) 0.03834(13) 0.0307(6) Uani 1 1 d . . . . .
C8 C 0.22093(10) 0.6808(3) 0.30373(15) 0.0303(6) Uani 1 1 d . . . . .
C5 C 0.07203(11) 0.1605(3) 0.27873(15) 0.0327(7) Uani 1 1 d . . . . .
H5 H 0.0515 0.0857 0.2655 0.039 Uiso 1 1 d R U . . .
C9 C 0.19791(12) 0.8133(3) 0.33009(17) 0.0409(8) Uani 1 1 d . . . . .
H9A H 0.1746 0.8493 0.2954 0.049 Uiso 1 1 d R U . . .
H9B H 0.2216 0.8852 0.3413 0.049 Uiso 1 1 d R U . . .
H9C H 0.1830 0.7892 0.3706 0.049 Uiso 1 1 d R U . . .
C11 C 0.25933(12) 0.6286(4) 0.3582(2) 0.0540(10) Uani 1 1 d . . . . .
H11A H 0.2466 0.6239 0.4018 0.065 Uiso 1 1 d R U . . .
H11B H 0.2855 0.6940 0.3612 0.065 Uiso 1 1 d R U . . .
H11C H 0.2699 0.5353 0.3460 0.065 Uiso 1 1 d R U . . .
C10 C 0.24209(11) 0.7135(4) 0.23713(17) 0.0430(8) Uani 1 1 d . . . . .
H10A H 0.2601 0.6326 0.2242 0.052 Uiso 1 1 d R U . . .
H10B H 0.2625 0.7952 0.2437 0.052 Uiso 1 1 d R U . . .
H10C H 0.2173 0.7334 0.2014 0.052 Uiso 1 1 d R U . . .
C15 C 0.12901(12) 0.3618(4) 0.00612(16) 0.0498(9) Uani 1 1 d . . . . .
H15A H 0.1280 0.4630 0.0143 0.060 Uiso 1 1 d R U . . .
H15B H 0.1258 0.3440 -0.0425 0.060 Uiso 1 1 d R U . . .
H15C H 0.1587 0.3241 0.0261 0.060 Uiso 1 1 d R U . . .
C16 C 0.0894(2) 0.1289(4) 0.02159(18) 0.0780(15) Uani 1 1 d . . . . .
H16A H 0.1174 0.0857 0.0443 0.094 Uiso 1 1 d R U . . .
H16B H 0.0892 0.1163 -0.0272 0.094 Uiso 1 1 d R U . . .
H16C H 0.0619 0.0843 0.0371 0.094 Uiso 1 1 d R U . . .


_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
Sb1 C1 2.089(2) . ?
Sb1 N1 2.434(2) . ?
Sb1 N2 2.441(2) . ?
Sb1 Cr1 2.7481(4) . ?
Cr1 C17 1.837(3) . ?
Cr1 C20 1.875(3) . ?
Cr1 C21 1.878(3) . ?
Cr1 C18 1.906(3) . ?
Cr1 C19 1.915(3) . ?
C12 N2 1.281(3) . ?
C12 C6 1.449(4) . ?
C12 H12 0.9300 . ?
C1 C6 1.393(4) . ?
C1 C2 1.396(4) . ?
C18 O2 1.142(3) . ?
N2 C13 1.494(3) . ?
O3 C19 1.137(3) . ?
N1 C7 1.286(3) . ?
N1 C8 1.499(3) . ?
O4 C20 1.146(3) . ?
O1 C17 1.153(3) . ?
O5 C21 1.126(3) . ?
C14 C13 1.504(4) . ?
C14 H14A 0.9602 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9599 . ?
C6 C5 1.391(4) . ?
C2 C3 1.400(4) . ?
C2 C7 1.451(4) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9301 . ?
C7 H7 0.9301 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9299 . ?
C13 C15 1.515(4) . ?
C13 C16 1.522(4) . ?
C8 C9 1.514(4) . ?
C8 C10 1.516(4) . ?
C8 C11 1.527(4) . ?
C5 H5 0.9299 . ?
C9 H9A 0.9601 . ?
C9 H9B 0.9601 . ?
C9 H9C 0.9599 . ?
C11 H11A 0.9601 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10 H10A 0.9601 . ?
C10 H10B 0.9601 . ?
C10 H10C 0.9601 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9598 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9599 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9601 . ?

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
C1 Sb1 N1 73.20(8) . . ?
C1 Sb1 N2 72.88(8) . . ?
N1 Sb1 N2 145.29(7) . . ?
C1 Sb1 Cr1 99.83(7) . . ?
N1 Sb1 Cr1 96.41(5) . . ?
N2 Sb1 Cr1 96.37(5) . . ?
C17 Cr1 C20 88.99(12) . . ?
C17 Cr1 C21 89.15(11) . . ?
C20 Cr1 C21 85.63(12) . . ?
C17 Cr1 C18 93.09(11) . . ?
C20 Cr1 C18 175.58(12) . . ?
C21 Cr1 C18 90.51(12) . . ?
C17 Cr1 C19 91.05(11) . . ?
C20 Cr1 C19 94.20(12) . . ?
C21 Cr1 C19 179.74(13) . . ?
C18 Cr1 C19 89.65(11) . . ?
C17 Cr1 Sb1 178.55(9) . . ?
C20 Cr1 Sb1 90.19(8) . . ?
C21 Cr1 Sb1 91.98(8) . . ?
C18 Cr1 Sb1 87.80(8) . . ?
C19 Cr1 Sb1 87.81(8) . . ?
N2 C12 C6 119.8(2) . . ?
N2 C12 H12 120.0 . . ?
C6 C12 H12 120.2 . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 Sb1 120.34(18) . . ?
C2 C1 Sb1 119.87(18) . . ?
O2 C18 Cr1 178.7(2) . . ?
C12 N2 C13 120.5(2) . . ?
C12 N2 Sb1 110.60(17) . . ?
C13 N2 Sb1 128.80(17) . . ?
C7 N1 C8 119.9(2) . . ?
C7 N1 Sb1 110.90(17) . . ?
C8 N1 Sb1 129.01(16) . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 110.0 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C17 Cr1 177.5(2) . . ?
O5 C21 Cr1 174.9(3) . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 C12 123.5(2) . . ?
C1 C6 C12 116.2(2) . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 C7 116.7(2) . . ?
C3 C2 C7 123.4(2) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.0 . . ?
O4 C20 Cr1 173.7(3) . . ?
N1 C7 C2 119.2(2) . . ?
N1 C7 H7 120.2 . . ?
C2 C7 H7 120.5 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
O3 C19 Cr1 177.7(2) . . ?
N2 C13 C14 108.5(2) . . ?
N2 C13 C15 107.3(2) . . ?
C14 C13 C15 110.3(3) . . ?
N2 C13 C16 111.3(2) . . ?
C14 C13 C16 109.7(3) . . ?
C15 C13 C16 109.7(3) . . ?
N1 C8 C9 108.5(2) . . ?
N1 C8 C10 107.1(2) . . ?
C9 C8 C10 110.4(3) . . ?
N1 C8 C11 111.5(2) . . ?
C9 C8 C11 109.1(3) . . ?
C10 C8 C11 110.2(3) . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 119.8 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.2 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C11 H11A 109.1 . . ?
C8 C11 H11B 109.6 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.8 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C10 H10A 109.4 . . ?
C8 C10 H10B 109.3 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.7 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C15 H15A 110.2 . . ?
C13 C15 H15B 109.3 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 108.9 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.4 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.250 0.500 186 48 ' '
2 0.250 -0.250 1.000 186 48 ' '
3 0.750 0.250 0.000 186 48 ' '
4 0.750 -0.250 0.500 186 48 ' '
_platon_squeeze_details          ?

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1515227'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT042_2c                  
;
PROBLEM: WARNING: Calc. and Reported MoietyFormula Strings ...  
RESPONSE: The structure contains more disorders.
Distances between Sb1 and W1 atoms 289.02(5)pm is a bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N2 O5 Sb W'
_chemical_formula_sum            'C21 H23 N2 O5 Sb W'
_chemical_formula_weight         689.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
W W -0.8490 6.8722 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5080(11)
_cell_length_b                   10.5261(16)
_cell_length_c                   11.4350(13)
_cell_angle_alpha                70.486(7)
_cell_angle_beta                 89.138(10)
_cell_angle_gamma                78.361(8)
_cell_volume                     1165.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    20983
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.963
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    6.121
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.056
0 0 -1 0.014
0 1 0 0.079
0 -1 0 0.053
-1 0 0 0.129
1 0 0 0.134
-1 1 0 0.116
1 -1 0 0.096


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.339
_exptl_absorpt_correction_T_max  0.679
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_reflns_number            20829
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_av_R_equivalents  0.0945
_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       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.892
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5337
_reflns_number_gt                4996
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²+1.9109P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5337
_refine_ls_number_parameters     295
_refine_ls_number_restraints     352
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
W1 W 0.81344(2) 0.76778(2) 0.11902(2) 0.02520(10) Uani 1 1 d . U . . .
Sb1 Sb 0.73304(3) 0.57313(3) 0.33712(3) 0.01984(11) Uani 1 1 d . U . . .
C18 C 0.6225(5) 0.8192(5) 0.0588(4) 0.0204(9) Uani 1 1 d . U . . .
C19 C 0.7955(6) 0.9109(6) 0.2025(6) 0.0326(12) Uani 1 1 d . U . . .
N1 N 0.5144(4) 0.7084(4) 0.3264(3) 0.0189(7) Uani 1 1 d . U . . .
O2 O 0.5159(4) 0.8458(4) 0.0230(4) 0.0292(8) Uani 1 1 d . U . . .
C1 C 0.6111(5) 0.4929(4) 0.2505(4) 0.0184(8) Uani 1 1 d . U . . .
C7 C 0.4324(5) 0.6661(5) 0.2754(4) 0.0214(9) Uani 1 1 d . U . . .
H7 H 0.3445 0.7077 0.2665 0.026 Uiso 1 1 d R U . . .
O3 O 0.7905(6) 0.9921(5) 0.2511(5) 0.0496(13) Uani 1 1 d . U . . .
C6 C 0.6613(5) 0.3751(5) 0.2200(4) 0.0211(9) Uani 1 1 d . U . . .
O1 O 0.8548(5) 0.5216(5) 0.0102(4) 0.0364(10) Uani 1 1 d . U . . .
C3 C 0.3979(5) 0.4966(5) 0.1727(5) 0.0259(10) Uani 1 1 d . U . . .
H3 H 0.3094 0.5355 0.1591 0.031 Uiso 1 1 d R U . . .
C8 C 0.4675(5) 0.8220(5) 0.3782(4) 0.0212(9) Uani 1 1 d . U . . .
N2 N 0.8638(4) 0.3668(4) 0.3112(4) 0.0232(8) Uani 1 1 d . U . . .
C17 C 0.8412(5) 0.6103(6) 0.0490(5) 0.0276(10) Uani 1 1 d . U . . .
C9 C 0.4535(6) 0.9597(5) 0.2721(5) 0.0269(11) Uani 1 1 d . U . . .
H9A H 0.5354 0.9661 0.2347 0.032 Uiso 1 1 d R U . . .
H9B H 0.4273 1.0340 0.3042 0.032 Uiso 1 1 d R U . . .
H9C H 0.3890 0.9656 0.2110 0.032 Uiso 1 1 d R U . . .
C5 C 0.5778(6) 0.3209(5) 0.1638(5) 0.0267(10) Uani 1 1 d . U . . .
H5 H 0.6106 0.2431 0.1425 0.032 Uiso 1 1 d R U . . .
C12 C 0.7971(5) 0.3119(5) 0.2556(5) 0.0233(10) Uani 1 1 d . U . . .
H12 H 0.8352 0.2325 0.2390 0.028 Uiso 1 1 d R U . . .
C13 C 0.9998(5) 0.2965(5) 0.3609(5) 0.0295(11) Uani 1 1 d D U . . .
C4 C 0.4488(6) 0.3816(6) 0.1408(6) 0.0304(11) Uani 1 1 d . U . . .
H4 H 0.3948 0.3466 0.1013 0.037 Uiso 1 1 d R U . . .
C2 C 0.4800(5) 0.5518(5) 0.2290(4) 0.0194(9) Uani 1 1 d . U . . .
C10 C 0.5715(6) 0.8069(6) 0.4770(5) 0.0342(12) Uani 1 1 d . U . . .
H10A H 0.5854 0.7160 0.5378 0.041 Uiso 1 1 d R U . . .
H10B H 0.5424 0.8739 0.5168 0.041 Uiso 1 1 d R U . . .
H10C H 0.6514 0.8220 0.4385 0.041 Uiso 1 1 d R U . . .
C11 C 0.3380(6) 0.8115(6) 0.4368(6) 0.0343(12) Uani 1 1 d . U . . .
H11A H 0.2711 0.8348 0.3724 0.041 Uiso 1 1 d R U . . .
H11B H 0.3191 0.8747 0.4820 0.041 Uiso 1 1 d R U . . .
H11C H 0.3412 0.7194 0.4924 0.041 Uiso 1 1 d R U . . .
C21A C 0.8875(18) 0.8782(18) -0.0221(14) 0.030(2) Uani 0.413(13) 1 d D U P A 2
O4A O 1.1096(9) 0.6654(12) 0.2433(12) 0.0468(18) Uani 0.486(9) 1 d D U P A 2
O5A O 0.9205(16) 0.9496(17) -0.1133(12) 0.046(2) Uani 0.413(13) 1 d D U P A 2
C20A C 1.0043(10) 0.6937(14) 0.2010(14) 0.0266(19) Uani 0.486(9) 1 d D U P A 2
C14A C 1.0854(11) 0.3165(13) 0.2555(10) 0.0324(15) Uani 0.461(7) 1 d D U P B 2
H14A H 1.0564 0.2794 0.1970 0.049 Uiso 0.461(7) 1 calc R U P B 2
H14B H 1.1731 0.2701 0.2854 0.049 Uiso 0.461(7) 1 calc R U P B 2
H14C H 1.0823 0.4132 0.2155 0.049 Uiso 0.461(7) 1 calc R U P B 2
C15A C 1.0017(12) 0.1389(9) 0.4203(12) 0.0330(16) Uani 0.461(7) 1 d D U P B 2
H15A H 0.9464 0.1240 0.4892 0.050 Uiso 0.461(7) 1 calc R U P B 2
H15B H 1.0890 0.0897 0.4490 0.050 Uiso 0.461(7) 1 calc R U P B 2
H15C H 0.9707 0.1063 0.3593 0.050 Uiso 0.461(7) 1 calc R U P B 2
C16A C 1.0277(13) 0.3458(14) 0.4627(10) 0.0348(16) Uani 0.461(7) 1 d D U P B 2
H16A H 0.9647 0.3264 0.5244 0.052 Uiso 0.461(7) 1 calc R U P B 2
H16B H 1.0234 0.4434 0.4301 0.052 Uiso 0.461(7) 1 calc R U P B 2
H16C H 1.1133 0.2997 0.4999 0.052 Uiso 0.461(7) 1 calc R U P B 2
O4 O 1.1079(9) 0.7312(11) 0.1828(12) 0.0468(18) Uani 0.514(9) 1 d D U P A 1
C16 C 0.9994(11) 0.2467(12) 0.4995(7) 0.0348(16) Uani 0.539(7) 1 d D U P B 1
H16D H 0.9511 0.3188 0.5262 0.052 Uiso 0.539(7) 1 calc R U P B 1
H16E H 1.0873 0.2214 0.5341 0.052 Uiso 0.539(7) 1 calc R U P B 1
H16F H 0.9597 0.1680 0.5272 0.052 Uiso 0.539(7) 1 calc R U P B 1
C14 C 1.0808(10) 0.4132(10) 0.3296(10) 0.0324(15) Uani 0.539(7) 1 d D U P B 1
H14D H 1.0413 0.4825 0.3639 0.049 Uiso 0.539(7) 1 calc R U P B 1
H14E H 1.0825 0.4542 0.2411 0.049 Uiso 0.539(7) 1 calc R U P B 1
H14F H 1.1682 0.3742 0.3647 0.049 Uiso 0.539(7) 1 calc R U P B 1
C15 C 1.0710(10) 0.1970(10) 0.3029(10) 0.0330(16) Uani 0.539(7) 1 d D U P B 1
H15D H 1.0647 0.2397 0.2141 0.050 Uiso 0.539(7) 1 calc R U P B 1
H15E H 1.0333 0.1168 0.3252 0.050 Uiso 0.539(7) 1 calc R U P B 1
H15F H 1.1609 0.1703 0.3320 0.050 Uiso 0.539(7) 1 calc R U P B 1
C20 C 0.9997(10) 0.7435(13) 0.1608(13) 0.0266(19) Uani 0.514(9) 1 d D U P A 1
C21 C 0.8467(13) 0.9185(13) -0.0407(10) 0.030(2) Uani 0.587(13) 1 d D U P A 1
O5 O 0.8640(11) 1.0010(12) -0.1336(8) 0.046(2) Uani 0.587(13) 1 d D U P A 1


_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
W1 C21A 1.906(12) . ?
W1 C20 1.967(10) . ?
W1 C19 2.014(6) . ?
W1 C18 2.037(5) . ?
W1 C17 2.040(5) . ?
W1 C21 2.060(9) . ?
W1 C20A 2.109(10) . ?
W1 Sb1 2.8902(5) . ?
Sb1 C1 2.090(5) . ?
Sb1 N1 2.427(4) . ?
Sb1 N2 2.430(4) . ?
C18 O2 1.145(7) . ?
C19 O3 1.158(7) . ?
N1 C7 1.275(7) . ?
N1 C8 1.500(6) . ?
C1 C2 1.381(7) . ?
C1 C6 1.399(6) . ?
C7 C2 1.467(6) . ?
C7 H7 0.9300 . ?
C6 C5 1.405(7) . ?
C6 C12 1.448(7) . ?
O1 C17 1.143(7) . ?
C3 C4 1.383(7) . ?
C3 C2 1.402(7) . ?
C3 H3 0.9300 . ?
C8 C11 1.516(8) . ?
C8 C9 1.529(6) . ?
C8 C10 1.531(7) . ?
N2 C12 1.285(7) . ?
N2 C13 1.493(7) . ?
C9 H9A 0.9601 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C5 C4 1.365(8) . ?
C5 H5 0.9300 . ?
C12 H12 0.9299 . ?
C13 C14A 1.476(8) . ?
C13 C16A 1.480(8) . ?
C13 C15 1.493(8) . ?
C13 C16 1.494(8) . ?
C13 C15A 1.565(8) . ?
C13 C14 1.576(8) . ?
C4 H4 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9601 . ?
C10 H10C 0.9599 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C21A O5A 1.159(9) . ?
O4A C20A 1.155(9) . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
O4 C20 1.141(8) . ?
C16 H16D 0.9600 . ?
C16 H16E 0.9600 . ?
C16 H16F 0.9600 . ?
C14 H14D 0.9600 . ?
C14 H14E 0.9600 . ?
C14 H14F 0.9600 . ?
C15 H15D 0.9600 . ?
C15 H15E 0.9600 . ?
C15 H15F 0.9600 . ?
C21 O5 1.165(8) . ?

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
C21A W1 C19 92.6(7) . . ?
C20 W1 C19 82.8(4) . . ?
C21A W1 C18 100.8(6) . . ?
C20 W1 C18 172.0(4) . . ?
C19 W1 C18 94.1(2) . . ?
C21A W1 C17 90.5(7) . . ?
C20 W1 C17 94.0(4) . . ?
C19 W1 C17 174.7(2) . . ?
C18 W1 C17 89.6(2) . . ?
C20 W1 C21 84.7(5) . . ?
C19 W1 C21 86.9(4) . . ?
C18 W1 C21 87.7(4) . . ?
C17 W1 C21 97.0(4) . . ?
C21A W1 C20A 86.6(7) . . ?
C19 W1 C20A 86.9(4) . . ?
C18 W1 C20A 172.5(4) . . ?
C17 W1 C20A 88.9(4) . . ?
C21A W1 Sb1 172.3(6) . . ?
C20 W1 Sb1 101.9(4) . . ?
C19 W1 Sb1 91.40(16) . . ?
C18 W1 Sb1 85.51(13) . . ?
C17 W1 Sb1 85.11(16) . . ?
C21 W1 Sb1 172.9(4) . . ?
C20A W1 Sb1 87.0(4) . . ?
C1 Sb1 N1 72.97(16) . . ?
C1 Sb1 N2 73.04(17) . . ?
N1 Sb1 N2 145.39(14) . . ?
C1 Sb1 W1 99.09(12) . . ?
N1 Sb1 W1 94.98(9) . . ?
N2 Sb1 W1 96.55(10) . . ?
O2 C18 W1 178.1(4) . . ?
O3 C19 W1 177.3(6) . . ?
C7 N1 C8 119.5(4) . . ?
C7 N1 Sb1 111.6(3) . . ?
C8 N1 Sb1 128.8(3) . . ?
C2 C1 C6 120.0(4) . . ?
C2 C1 Sb1 120.1(3) . . ?
C6 C1 Sb1 119.8(4) . . ?
N1 C7 C2 118.6(5) . . ?
N1 C7 H7 120.7 . . ?
C2 C7 H7 120.7 . . ?
C1 C6 C5 119.2(5) . . ?
C1 C6 C12 116.8(4) . . ?
C5 C6 C12 123.9(5) . . ?
C4 C3 C2 119.6(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.2 . . ?
N1 C8 C11 111.9(4) . . ?
N1 C8 C9 108.2(4) . . ?
C11 C8 C9 109.6(4) . . ?
N1 C8 C10 106.2(4) . . ?
C11 C8 C10 109.7(4) . . ?
C9 C8 C10 111.2(4) . . ?
C12 N2 C13 120.3(4) . . ?
C12 N2 Sb1 111.3(3) . . ?
C13 N2 Sb1 128.1(3) . . ?
O1 C17 W1 178.9(5) . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.3 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C5 C6 120.2(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 119.8 . . ?
N2 C12 C6 119.0(4) . . ?
N2 C12 H12 120.5 . . ?
C6 C12 H12 120.5 . . ?
C14A C13 C16A 118.4(8) . . ?
C14A C13 N2 108.3(6) . . ?
C16A C13 N2 106.9(6) . . ?
N2 C13 C15 117.0(6) . . ?
N2 C13 C16 107.6(6) . . ?
C15 C13 C16 116.7(7) . . ?
C14A C13 C15A 108.4(8) . . ?
C16A C13 C15A 107.2(8) . . ?
N2 C13 C15A 107.2(6) . . ?
N2 C13 C14 106.1(5) . . ?
C15 C13 C14 103.9(7) . . ?
C16 C13 C14 104.0(7) . . ?
C5 C4 C3 120.9(5) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.5 . . ?
C1 C2 C3 120.1(4) . . ?
C1 C2 C7 116.7(4) . . ?
C3 C2 C7 123.1(5) . . ?
C8 C10 H10A 109.8 . . ?
C8 C10 H10B 109.0 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.6 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.0 . . ?
C8 C11 H11B 109.3 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 110.1 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5A C21A W1 173.4(16) . . ?
O4A C20A W1 173.8(11) . . ?
C13 C14A H14A 109.5 . . ?
C13 C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13 C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13 C15A H15A 109.5 . . ?
C13 C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C13 C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C13 C16A H16A 109.5 . . ?
C13 C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C13 C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C13 C16 H16D 109.5 . . ?
C13 C16 H16E 109.5 . . ?
H16D C16 H16E 109.5 . . ?
C13 C16 H16F 109.5 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C13 C14 H14D 109.5 . . ?
C13 C14 H14E 109.5 . . ?
H14D C14 H14E 109.5 . . ?
C13 C14 H14F 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
C13 C15 H15D 109.5 . . ?
C13 C15 H15E 109.5 . . ?
H15D C15 H15E 109.5 . . ?
C13 C15 H15F 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
O4 C20 W1 178.7(13) . . ?
O5 C21 W1 177.4(12) . . ?

_refine_diff_density_max         3.563
_refine_diff_density_min         -4.001
_refine_diff_density_rms         0.243
####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1515228'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C21 H23 Bi Cr N2 O5), C7 H8'
_chemical_formula_sum            'C49 H54 Bi2 Cr2 N4 O10'
_chemical_formula_weight         1380.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Cr Cr 0.3209 0.6236 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.3042(13)
_cell_length_b                   19.3039(14)
_cell_length_c                   13.576(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5059.1(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    38605
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_F_000             2680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    7.413
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.220
0 1 0 0.276
0 -1 -1 0.217
0 0 -1 0.244
0 0 1 0.213
0 1 1 0.244
-1 0 0 0.049
1 0 0 0.047
0 1 -1 0.273
0 -1 1 0.228


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.085
_exptl_absorpt_correction_T_max  0.493
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_reflns_number            38570
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.834
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             11036
_reflns_number_gt                9184
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_max     0.920
_reflns_Friedel_fraction_full    0.973

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+35.3879P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3645 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.015(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         11036
_refine_ls_number_parameters     604
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0833
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.60094(2) 0.48151(2) 0.68098(3) 0.02129(10) Uani 1 1 d . . . . .
Bi2 Bi 0.90205(2) 0.83131(2) 0.67599(3) 0.01889(9) Uani 1 1 d . . . . .
Cr3 Cr 0.89958(11) 0.84387(8) 0.88106(12) 0.0193(3) Uani 1 1 d . . . . .
Cr4 Cr 0.58519(9) 0.49354(9) 0.88636(13) 0.0188(4) Uani 1 1 d . . . . .
N1 N 0.4914(5) 0.4154(5) 0.6554(7) 0.025(2) Uani 1 1 d . . . . .
C119 C 0.9987(6) 0.8382(6) 0.8785(9) 0.023(3) Uani 1 1 d . . . . .
N3 N 0.8429(5) 0.9489(5) 0.6396(7) 0.022(2) Uani 1 1 d . . . . .
C20 C 0.4884(6) 0.4852(6) 0.8732(9) 0.027(3) Uani 1 1 d . . . . .
C4 C 0.4127(7) 0.6484(7) 0.5991(9) 0.035(3) Uani 1 1 d . . . . .
H4 H 0.3770 0.6799 0.5891 0.041 Uiso 1 1 d R U . . .
O6 O 0.9001(6) 0.8656(4) 1.1002(6) 0.036(2) Uani 1 1 d . . . . .
C118 C 0.8953(7) 0.7468(6) 0.8965(8) 0.022(2) Uani 1 1 d . . . . .
C108 C 0.7672(6) 0.9644(7) 0.6311(9) 0.029(3) Uani 1 1 d . . . . .
C6 C 0.5343(6) 0.6247(6) 0.6261(9) 0.024(3) Uani 1 1 d . . . . .
O4 O 0.4298(4) 0.4786(5) 0.8674(7) 0.037(2) Uani 1 1 d . . . . .
C112 C 1.0665(6) 0.8175(6) 0.6494(8) 0.025(3) Uani 1 1 d . . . . .
H112 H 1.1120 0.8019 0.6450 0.030 Uiso 1 1 d R U . . .
C21 C 0.5902(6) 0.3970(6) 0.9029(8) 0.025(2) Uani 1 1 d . . . . .
C18 C 0.6818(7) 0.5005(6) 0.8967(9) 0.028(3) Uani 1 1 d . . . . .
O7 O 0.8932(6) 0.6884(4) 0.9087(6) 0.038(2) Uani 1 1 d . . . . .
C105 C 1.1012(7) 0.9411(5) 0.6238(8) 0.026(2) Uani 1 1 d . . . . .
H105 H 1.1479 0.9295 0.6225 0.032 Uiso 1 1 d R U . . .
C117 C 0.9000(7) 0.8568(5) 1.0165(8) 0.024(2) Uani 1 1 d . . . . .
C120 C 0.9039(7) 0.9408(6) 0.8637(8) 0.025(2) Uani 1 1 d . . . . .
O8 O 1.0570(5) 0.8342(5) 0.8819(7) 0.035(2) Uani 1 1 d . . . . .
N2 N 0.6544(6) 0.6036(5) 0.6539(7) 0.028(2) Uani 1 1 d . . . . .
N4 N 1.0187(5) 0.7734(5) 0.6620(7) 0.023(2) Uani 1 1 d . . . . .
C3 C 0.3979(7) 0.5783(6) 0.6119(9) 0.030(3) Uani 1 1 d . . . . .
H3 H 0.3531 0.5620 0.6031 0.036 Uiso 1 1 d R U . . .
C113 C 1.0363(6) 0.6973(5) 0.6642(9) 0.026(3) Uani 1 1 d . . . . .
C103 C 1.0136(7) 1.0282(6) 0.6129(9) 0.026(3) Uani 1 1 d . . . . .
H103 H 1.0019 1.0746 0.6045 0.031 Uiso 1 1 d R U . . .
C101 C 0.9815(6) 0.9108(5) 0.6460(8) 0.019(2) Uani 1 1 d . . . . .
C5 C 0.4809(7) 0.6713(6) 0.6050(9) 0.027(3) Uani 1 1 d . . . . .
H5 H 0.4923 0.7174 0.5932 0.032 Uiso 1 1 d R U . . .
O9 O 0.9050(5) 1.0002(4) 0.8559(6) 0.034(2) Uani 1 1 d . . . . .
C114 C 0.9691(6) 0.6576(6) 0.6692(11) 0.032(3) Uani 1 1 d . . . . .
114A H 0.9461 0.6688 0.7298 0.039 Uiso 1 1 d R U . . .
114B H 0.9399 0.6700 0.6147 0.039 Uiso 1 1 d R U . . .
114C H 0.9785 0.6088 0.6671 0.039 Uiso 1 1 d R U . . .
C107 C 0.8886(6) 0.9952(6) 0.6242(8) 0.023(3) Uani 1 1 d . . . . .
H107 H 0.8751 1.0405 0.6106 0.028 Uiso 1 1 d R U . . .
O3 O 0.5685(5) 0.6488(4) 0.8571(7) 0.035(2) Uani 1 1 d . . . . .
C7 C 0.4402(6) 0.4562(6) 0.6383(8) 0.024(2) Uani 1 1 d . . . . .
H7 H 0.3960 0.4382 0.6287 0.029 Uiso 1 1 d R U . . .
O1 O 0.5717(5) 0.5114(5) 1.1052(6) 0.036(2) Uani 1 1 d . . . . .
C9 C 0.4443(8) 0.3170(7) 0.5601(9) 0.031(3) Uani 1 1 d . . . . .
H9A H 0.4707 0.3324 0.5042 0.037 Uiso 1 1 d R U . . .
H9B H 0.4427 0.2673 0.5606 0.037 Uiso 1 1 d R U . . .
H9C H 0.3981 0.3350 0.5559 0.037 Uiso 1 1 d R U . . .
C115 C 1.0798(7) 0.6815(7) 0.7558(11) 0.039(4) Uani 1 1 d . . . . .
115A H 1.1194 0.7115 0.7587 0.046 Uiso 1 1 d R U . . .
115B H 1.0526 0.6871 0.8145 0.046 Uiso 1 1 d R U . . .
115C H 1.0949 0.6343 0.7507 0.046 Uiso 1 1 d R U . . .
C10 C 0.4341(7) 0.3204(7) 0.7428(9) 0.030(3) Uani 1 1 d . . . . .
H10A H 0.4010 0.2856 0.7245 0.036 Uiso 1 1 d R U . . .
H10B H 0.4636 0.3027 0.7939 0.036 Uiso 1 1 d R U . . .
H10C H 0.4102 0.3607 0.7664 0.036 Uiso 1 1 d R U . . .
C19 C 0.5767(6) 0.5898(6) 0.8672(8) 0.023(2) Uani 1 1 d . . . . .
C102 C 0.9623(6) 0.9790(6) 0.6287(9) 0.022(2) Uani 1 1 d . . . . .
O2 O 0.7414(5) 0.5034(6) 0.9068(8) 0.040(2) Uani 1 1 d . . . . .
C116 C 1.0737(10) 0.6778(7) 0.5716(11) 0.046(5) Uani 1 1 d . . . . .
116A H 1.0897 0.6307 0.5746 0.055 Uiso 1 1 d R U . . .
116B H 1.0409 0.6825 0.5189 0.055 Uiso 1 1 d R U . . .
116C H 1.1123 0.7081 0.5601 0.055 Uiso 1 1 d R U . . .
C8 C 0.4792(6) 0.3392(6) 0.6561(8) 0.023(3) Uani 1 1 d . . . . .
C121 C 0.8016(7) 0.8445(6) 0.8783(9) 0.028(3) Uani 1 1 d . . . . .
C17 C 0.5763(6) 0.5046(5) 1.0199(10) 0.023(3) Uani 1 1 d . . . . .
C11 C 0.5503(7) 0.3059(6) 0.6666(10) 0.035(3) Uani 1 1 d . . . . .
H11A H 0.5631 0.3069 0.7349 0.042 Uiso 1 1 d R U . . .
H11B H 0.5467 0.2587 0.6449 0.042 Uiso 1 1 d R U . . .
H11C H 0.5850 0.3294 0.6284 0.042 Uiso 1 1 d R U . . .
C109 C 0.7310(7) 0.8962(8) 0.6138(12) 0.043(4) Uani 1 1 d . . . . .
109A H 0.7346 0.8691 0.6730 0.052 Uiso 1 1 d R U . . .
109B H 0.6830 0.9041 0.5988 0.052 Uiso 1 1 d R U . . .
109C H 0.7524 0.8717 0.5604 0.052 Uiso 1 1 d R U . . .
O5 O 0.5929(6) 0.3382(4) 0.9186(6) 0.036(2) Uani 1 1 d . . . . .
C110 C 0.7517(7) 1.0161(9) 0.5481(11) 0.050(4) Uani 1 1 d . . . . .
110A H 0.7706 1.0003 0.4867 0.060 Uiso 1 1 d R U . . .
110B H 0.7023 1.0199 0.5426 0.060 Uiso 1 1 d R U . . .
110C H 0.7709 1.0606 0.5640 0.060 Uiso 1 1 d R U . . .
C12 C 0.6072(7) 0.6461(6) 0.6323(8) 0.028(3) Uani 1 1 d . . . . .
H12 H 0.6183 0.6922 0.6204 0.034 Uiso 1 1 d R U . . .
C2 C 0.4514(6) 0.5314(6) 0.6324(9) 0.024(2) Uani 1 1 d . . . . .
C106 C 1.0506(6) 0.8913(6) 0.6418(9) 0.022(2) Uani 1 1 d . . . . .
O10 O 0.7430(5) 0.8434(6) 0.8792(8) 0.043(2) Uani 1 1 d . . . . .
C1 C 0.5194(7) 0.5543(6) 0.6422(9) 0.027(3) Uani 1 1 d . . . . .
C104 C 1.0826(6) 1.0098(7) 0.6114(10) 0.031(3) Uani 1 1 d . . . . .
H104 H 1.1160 1.0431 0.5980 0.037 Uiso 1 1 d R U . . .
C16 C 0.7371(8) 0.6707(9) 0.7501(11) 0.046(4) Uani 1 1 d . . . . .
H16A H 0.6936 0.6780 0.7828 0.055 Uiso 1 1 d R U . . .
H16B H 0.7686 0.6479 0.7942 0.055 Uiso 1 1 d R U . . .
H16C H 0.7562 0.7145 0.7306 0.055 Uiso 1 1 d R U . . .
C111 C 0.7443(8) 0.9965(9) 0.7290(11) 0.043(4) Uani 1 1 d . . . . .
111A H 0.7646 1.0419 0.7289 0.052 Uiso 1 1 d R U . . .
111B H 0.6948 1.0004 0.7325 0.052 Uiso 1 1 d R U . . .
111C H 0.7608 0.9709 0.7849 0.052 Uiso 1 1 d R U . . .
C13 C 0.7264(7) 0.6280(7) 0.6572(9) 0.031(3) Uani 1 1 d . . . . .
C27 C 0.7340(8) 0.6500(8) 0.1927(13) 0.048(4) Uani 1 1 d . . . . .
H27 H 0.7181 0.6052 0.1813 0.057 Uiso 1 1 calc R U . . .
C23 C 0.7593(8) 0.7633(9) 0.1366(12) 0.047(4) Uani 1 1 d . . . . .
H23 H 0.7617 0.7950 0.0850 0.057 Uiso 1 1 calc R U . . .
C22 C 0.7368(7) 0.6957(8) 0.1175(11) 0.039(4) Uani 1 1 d . . . . .
C14 C 0.7484(10) 0.6682(11) 0.5670(11) 0.057(5) Uani 1 1 d . . . . .
H14A H 0.7149 0.7035 0.5525 0.069 Uiso 1 1 d R U . . .
H14B H 0.7929 0.6892 0.5773 0.069 Uiso 1 1 d R U . . .
H14C H 0.7511 0.6365 0.5127 0.069 Uiso 1 1 d R U . . .
C15 C 0.7727(7) 0.5634(8) 0.6621(13) 0.047(4) Uani 1 1 d . . . . .
H15A H 0.7579 0.5297 0.6145 0.057 Uiso 1 1 d R U . . .
H15B H 0.8189 0.5782 0.6468 0.057 Uiso 1 1 d R U . . .
H15C H 0.7719 0.5431 0.7266 0.057 Uiso 1 1 d R U . . .
C28 C 0.7172(10) 0.6761(11) 0.0150(12) 0.065(5) Uani 1 1 d . . . . .
H28A H 0.7496 0.6946 -0.0317 0.078 Uiso 1 1 d R U . . .
H28B H 0.7186 0.6264 0.0129 0.078 Uiso 1 1 d R U . . .
H28C H 0.6713 0.6916 -0.0012 0.078 Uiso 1 1 d R U . . .
C25 C 0.7745(8) 0.7358(8) 0.3053(11) 0.046(4) Uani 1 1 d . . . . .
H25 H 0.7856 0.7484 0.3695 0.055 Uiso 1 1 calc R U . . .
C24 C 0.7786(8) 0.7845(8) 0.2320(11) 0.047(4) Uani 1 1 d . . . . .
H24 H 0.7934 0.8294 0.2447 0.056 Uiso 1 1 calc R U . . .
C26 C 0.7545(8) 0.6692(9) 0.2865(14) 0.053(4) Uani 1 1 d . . . . .
H26 H 0.7546 0.6366 0.3370 0.063 Uiso 1 1 calc R U . . .


_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
Bi1 C1 2.175(13) . ?
Bi1 N1 2.494(10) . ?
Bi1 N2 2.598(10) . ?
Bi1 Cr4 2.814(2) . ?
Bi2 C101 2.207(11) . ?
Bi2 N4 2.521(9) . ?
Bi2 N3 2.588(9) . ?
Bi2 Cr3 2.7950(18) . ?
Cr3 C117 1.856(11) . ?
Cr3 C118 1.886(11) . ?
Cr3 C120 1.888(11) . ?
Cr3 C121 1.892(14) . ?
Cr3 C119 1.916(12) . ?
Cr4 C17 1.834(13) . ?
Cr4 C18 1.874(14) . ?
Cr4 C21 1.880(12) . ?
Cr4 C19 1.883(11) . ?
Cr4 C20 1.885(13) . ?
N1 C7 1.285(15) . ?
N1 C8 1.491(14) . ?
C119 O8 1.130(15) . ?
N3 C107 1.273(15) . ?
N3 C108 1.497(14) . ?
C20 O4 1.140(15) . ?
C4 C5 1.390(19) . ?
C4 C3 1.392(18) . ?
C4 H4 0.9300 . ?
O6 C117 1.149(13) . ?
C118 O7 1.140(13) . ?
C108 C109 1.510(19) . ?
C108 C111 1.531(19) . ?
C108 C110 1.534(19) . ?
C6 C5 1.398(17) . ?
C6 C1 1.406(16) . ?
C6 C12 1.469(18) . ?
C112 N4 1.266(14) . ?
C112 C106 1.461(16) . ?
C112 H112 0.9300 . ?
C21 O5 1.156(13) . ?
C18 O2 1.161(16) . ?
C105 C104 1.383(17) . ?
C105 C106 1.392(16) . ?
C105 H105 0.9301 . ?
C120 O9 1.151(13) . ?
N2 C12 1.260(16) . ?
N2 C13 1.469(15) . ?
N4 C113 1.508(13) . ?
C3 C2 1.401(17) . ?
C3 H3 0.9300 . ?
C113 C116 1.499(18) . ?
C113 C114 1.509(16) . ?
C113 C115 1.531(17) . ?
C103 C104 1.379(17) . ?
C103 C102 1.389(16) . ?
C103 H103 0.9301 . ?
C101 C106 1.388(16) . ?
C101 C102 1.388(15) . ?
C5 H5 0.9301 . ?
C114 114A 0.9600 . ?
C114 114B 0.9600 . ?
C114 114C 0.9600 . ?
C107 C102 1.458(16) . ?
C107 H107 0.9300 . ?
O3 C19 1.158(14) . ?
C7 C2 1.470(16) . ?
C7 H7 0.9301 . ?
O1 C17 1.169(15) . ?
C9 C8 1.529(16) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9599 . ?
C9 H9C 0.9601 . ?
C115 115A 0.9600 . ?
C115 115B 0.9599 . ?
C115 115C 0.9601 . ?
C10 C8 1.508(16) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9599 . ?
C10 H10C 0.9599 . ?
C116 116A 0.9600 . ?
C116 116B 0.9601 . ?
C116 116C 0.9600 . ?
C8 C11 1.523(17) . ?
C121 O10 1.132(16) . ?
C11 H11A 0.9599 . ?
C11 H11B 0.9601 . ?
C11 H11C 0.9601 . ?
C109 109A 0.9601 . ?
C109 109B 0.9601 . ?
C109 109C 0.9600 . ?
C110 110A 0.9601 . ?
C110 110B 0.9599 . ?
C110 110C 0.9599 . ?
C12 H12 0.9299 . ?
C2 C1 1.392(17) . ?
C104 H104 0.9298 . ?
C16 C13 1.520(18) . ?
C16 H16A 0.9601 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9598 . ?
C111 111A 0.9600 . ?
C111 111B 0.9599 . ?
C111 111C 0.9602 . ?
C13 C14 1.51(2) . ?
C13 C15 1.536(19) . ?
C27 C22 1.35(2) . ?
C27 C26 1.38(2) . ?
C27 H27 0.9300 . ?
C23 C22 1.40(2) . ?
C23 C24 1.41(2) . ?
C23 H23 0.9300 . ?
C22 C28 1.49(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9598 . ?
C14 H14C 0.9602 . ?
C15 H15A 0.9599 . ?
C15 H15B 0.9601 . ?
C15 H15C 0.9600 . ?
C28 H28A 0.9601 . ?
C28 H28B 0.9601 . ?
C28 H28C 0.9600 . ?
C25 C24 1.37(2) . ?
C25 C26 1.37(2) . ?
C25 H25 0.9300 . ?
C24 H24 0.9300 . ?
C26 H26 0.9300 . ?

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
C1 Bi1 N1 71.5(4) . . ?
C1 Bi1 N2 70.5(4) . . ?
N1 Bi1 N2 141.3(3) . . ?
C1 Bi1 Cr4 96.2(3) . . ?
N1 Bi1 Cr4 95.1(2) . . ?
N2 Bi1 Cr4 96.2(2) . . ?
C101 Bi2 N4 70.9(4) . . ?
C101 Bi2 N3 70.2(4) . . ?
N4 Bi2 N3 140.2(3) . . ?
C101 Bi2 Cr3 97.8(3) . . ?
N4 Bi2 Cr3 97.4(2) . . ?
N3 Bi2 Cr3 96.1(2) . . ?
C117 Cr3 C118 91.3(5) . . ?
C117 Cr3 C120 89.5(5) . . ?
C118 Cr3 C120 179.2(5) . . ?
C117 Cr3 C121 91.4(6) . . ?
C118 Cr3 C121 88.0(5) . . ?
C120 Cr3 C121 92.0(6) . . ?
C117 Cr3 C119 91.2(6) . . ?
C118 Cr3 C119 89.4(5) . . ?
C120 Cr3 C119 90.6(5) . . ?
C121 Cr3 C119 176.4(5) . . ?
C117 Cr3 Bi2 177.0(3) . . ?
C118 Cr3 Bi2 91.4(3) . . ?
C120 Cr3 Bi2 87.8(3) . . ?
C121 Cr3 Bi2 89.9(4) . . ?
C119 Cr3 Bi2 87.7(4) . . ?
C17 Cr4 C18 90.6(5) . . ?
C17 Cr4 C21 90.1(5) . . ?
C18 Cr4 C21 90.6(5) . . ?
C17 Cr4 C19 90.8(5) . . ?
C18 Cr4 C19 91.5(5) . . ?
C21 Cr4 C19 177.7(5) . . ?
C17 Cr4 C20 90.6(5) . . ?
C18 Cr4 C20 178.6(6) . . ?
C21 Cr4 C20 88.8(5) . . ?
C19 Cr4 C20 89.1(5) . . ?
C17 Cr4 Bi1 177.9(4) . . ?
C18 Cr4 Bi1 88.4(4) . . ?
C21 Cr4 Bi1 91.8(3) . . ?
C19 Cr4 Bi1 87.3(3) . . ?
C20 Cr4 Bi1 90.3(4) . . ?
C7 N1 C8 118.9(10) . . ?
C7 N1 Bi1 111.4(8) . . ?
C8 N1 Bi1 129.7(7) . . ?
O8 C119 Cr3 176.6(11) . . ?
C107 N3 C108 121.6(10) . . ?
C107 N3 Bi2 110.0(7) . . ?
C108 N3 Bi2 128.4(8) . . ?
O4 C20 Cr4 177.9(12) . . ?
C5 C4 C3 119.8(12) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
O7 C118 Cr3 177.9(10) . . ?
N3 C108 C109 106.9(10) . . ?
N3 C108 C111 107.2(10) . . ?
C109 C108 C111 110.7(12) . . ?
N3 C108 C110 112.1(10) . . ?
C109 C108 C110 111.3(12) . . ?
C111 C108 C110 108.5(12) . . ?
C5 C6 C1 120.2(12) . . ?
C5 C6 C12 122.6(11) . . ?
C1 C6 C12 117.2(11) . . ?
N4 C112 C106 120.8(11) . . ?
N4 C112 H112 118.7 . . ?
C106 C112 H112 120.5 . . ?
O5 C21 Cr4 176.1(10) . . ?
O2 C18 Cr4 177.2(12) . . ?
C104 C105 C106 120.1(12) . . ?
C104 C105 H105 118.8 . . ?
C106 C105 H105 121.1 . . ?
O6 C117 Cr3 179.2(10) . . ?
O9 C120 Cr3 177.6(11) . . ?
C12 N2 C13 118.8(11) . . ?
C12 N2 Bi1 109.7(8) . . ?
C13 N2 Bi1 131.5(8) . . ?
C112 N4 C113 119.5(10) . . ?
C112 N4 Bi2 111.3(7) . . ?
C113 N4 Bi2 129.2(7) . . ?
C4 C3 C2 120.1(13) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 119.5 . . ?
C116 C113 N4 109.7(10) . . ?
C116 C113 C114 108.9(12) . . ?
N4 C113 C114 107.6(9) . . ?
C116 C113 C115 111.5(12) . . ?
N4 C113 C115 109.5(10) . . ?
C114 C113 C115 109.5(11) . . ?
C104 C103 C102 120.9(11) . . ?
C104 C103 H103 118.8 . . ?
C102 C103 H103 120.3 . . ?
C106 C101 C102 120.4(10) . . ?
C106 C101 Bi2 119.2(8) . . ?
C102 C101 Bi2 120.4(8) . . ?
C4 C5 C6 120.3(11) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 118.3 . . ?
C113 C114 114A 108.8 . . ?
C113 C114 114B 110.1 . . ?
114A C114 114B 109.5 . . ?
C113 C114 114C 109.5 . . ?
114A C114 114C 109.5 . . ?
114B C114 114C 109.5 . . ?
N3 C107 C102 121.2(10) . . ?
N3 C107 H107 119.8 . . ?
C102 C107 H107 119.0 . . ?
N1 C7 C2 120.1(11) . . ?
N1 C7 H7 120.1 . . ?
C2 C7 H7 119.8 . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 106.7 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 110.9 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C113 C115 115A 110.5 . . ?
C113 C115 115B 110.6 . . ?
115A C115 115B 109.5 . . ?
C113 C115 115C 107.3 . . ?
115A C115 115C 109.5 . . ?
115B C115 115C 109.5 . . ?
C8 C10 H10A 110.5 . . ?
C8 C10 H10B 107.9 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 110.0 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C19 Cr4 176.8(10) . . ?
C103 C102 C101 119.1(11) . . ?
C103 C102 C107 122.8(11) . . ?
C101 C102 C107 118.1(11) . . ?
C113 C116 116A 111.0 . . ?
C113 C116 116B 106.4 . . ?
116A C116 116B 109.5 . . ?
C113 C116 116C 111.0 . . ?
116A C116 116C 109.5 . . ?
116B C116 116C 109.5 . . ?
N1 C8 C10 109.5(9) . . ?
N1 C8 C11 105.9(9) . . ?
C10 C8 C11 110.2(10) . . ?
N1 C8 C9 109.9(9) . . ?
C10 C8 C9 110.2(10) . . ?
C11 C8 C9 111.0(10) . . ?
O10 C121 Cr3 177.7(12) . . ?
O1 C17 Cr4 178.9(10) . . ?
C8 C11 H11A 108.3 . . ?
C8 C11 H11B 107.8 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 112.3 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C108 C109 109A 108.1 . . ?
C108 C109 109B 109.9 . . ?
109A C109 109B 109.5 . . ?
C108 C109 109C 110.4 . . ?
109A C109 109C 109.5 . . ?
109B C109 109C 109.5 . . ?
C108 C110 110A 110.9 . . ?
C108 C110 110B 107.5 . . ?
110A C110 110B 109.5 . . ?
C108 C110 110C 110.0 . . ?
110A C110 110C 109.5 . . ?
110B C110 110C 109.5 . . ?
N2 C12 C6 121.6(11) . . ?
N2 C12 H12 119.8 . . ?
C6 C12 H12 118.6 . . ?
C1 C2 C3 120.5(11) . . ?
C1 C2 C7 116.6(11) . . ?
C3 C2 C7 122.7(12) . . ?
C101 C106 C105 119.6(11) . . ?
C101 C106 C112 117.6(10) . . ?
C105 C106 C112 122.6(11) . . ?
C2 C1 C6 119.0(12) . . ?
C2 C1 Bi1 120.0(8) . . ?
C6 C1 Bi1 121.0(9) . . ?
C103 C104 C105 119.8(11) . . ?
C103 C104 H104 119.6 . . ?
C105 C104 H104 120.4 . . ?
C13 C16 H16A 110.1 . . ?
C13 C16 H16B 110.8 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 107.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C108 C111 111A 104.5 . . ?
C108 C111 111B 111.3 . . ?
111A C111 111B 109.5 . . ?
C108 C111 111C 112.5 . . ?
111A C111 111C 109.5 . . ?
111B C111 111C 109.5 . . ?
N2 C13 C14 114.0(12) . . ?
N2 C13 C16 109.2(11) . . ?
C14 C13 C16 110.9(12) . . ?
N2 C13 C15 106.9(10) . . ?
C14 C13 C15 106.8(13) . . ?
C16 C13 C15 109.0(12) . . ?
C22 C27 C26 120.5(15) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C22 C23 C24 121.5(15) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C27 C22 C23 118.9(15) . . ?
C27 C22 C28 121.9(15) . . ?
C23 C22 C28 119.2(16) . . ?
C13 C14 H14A 109.9 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 108.0 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 110.4 . . ?
C13 C15 H15B 106.7 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 111.2 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 C28 H28A 110.9 . . ?
C22 C28 H28B 105.9 . . ?
H28A C28 H28B 109.5 . . ?
C22 C28 H28C 111.6 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C25 C26 121.7(15) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C25 C24 C23 117.0(14) . . ?
C25 C24 H24 121.5 . . ?
C23 C24 H24 121.5 . . ?
C25 C26 C27 120.4(16) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?

_refine_diff_density_max         1.833
_refine_diff_density_min         -1.623
_refine_diff_density_rms         0.189
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1515229'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_CHEMW03_2b                  
;
PROBLEM: WARNING: The ratio of given/expected molecular ...  
RESPONSE: The structure contains disorder of toluene.
The platon SQUEEZE program was used.
;
_vrf_CELLZ01_2b                  
;
PROBLEM: WARNING:  Difference between formula and atom_site ...  
RESPONSE: The structure contains disorder of toluene.
The platon SQUEEZE program was used.
;
_vrf_FORMU01_2b                  
;
PROBLEM: There is a discrepancy between the atom ...  
RESPONSE: The structure contains disorder of toluene.
The platon SQUEEZE program was used.
;
_vrf_PLAT041_2b                  
;
PROBLEM: WARNING:  Calc. and Reported SumFormula ...  
RESPONSE: The structure contains disorder of toluene.
The platon SQUEEZE program was used.
;
_vrf_PLAT990_2b                  
;
PROBLEM: Depricated RES file style based SQUEEZE job ...  
RESPONSE: The structure contains disorder of toluene.
The platon SQUEEZE program was used.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 Mo N2 O5 Sb, 0.25(C7 H8)'
_chemical_formula_sum            'C22.75 H25 Mo N2 O5 Sb'
_chemical_formula_weight         624.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Mo Mo -1.6832 0.6857 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   28.7432(3)
_cell_length_b                   9.4385(7)
_cell_length_c                   19.6321(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.060(2)
_cell_angle_gamma                90
_cell_volume                     5296.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    25513
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             2468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.525
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.140
-1 0 0 0.173
-1 -1 1 0.087
-1 1 0 0.058
0 0 -1 0.041
0 0 1 0.045
-1 0 1 0.128
1 -1 1 0.123
1 1 -1 0.112


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_reflns_number            25340
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.034
_diffrn_reflns_theta_max         27.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             5821
_reflns_number_gt                5160
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+11.8534P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5821
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0586
_refine_ls_wR_factor_gt          0.0528
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.14690(2) 0.49630(2) 0.17639(2) 0.02030(5) Uani 1 1 d . . . . .
Mo1 Mo 0.07454(2) 0.71030(2) 0.16851(2) 0.02072(5) Uani 1 1 d . . . . .
O1 O 0.08195(7) 0.7010(2) 0.33165(9) 0.0407(5) Uani 1 1 d . . . . .
N2 N 0.09906(7) 0.3188(2) 0.11358(9) 0.0245(4) Uani 1 1 d . . . . .
C3 C 0.11963(9) 0.2901(3) 0.36637(12) 0.0344(6) Uani 1 1 d . . . . .
H3 H 0.1295 0.3015 0.4127 0.041 Uiso 1 1 d R U . . .
C12 C 0.08086(8) 0.2341(2) 0.15452(11) 0.0262(5) Uani 1 1 d . . . . .
H12 H 0.0614 0.1609 0.1374 0.031 Uiso 1 1 d R U . . .
C2 C 0.13686(8) 0.3799(2) 0.31811(11) 0.0244(4) Uani 1 1 d . . . . .
O4 O 0.14644(7) 0.9633(3) 0.17160(13) 0.0557(6) Uani 1 1 d . . . . .
C10 C 0.19722(11) 0.8108(3) 0.32979(16) 0.0436(7) Uani 1 1 d . . . . .
H10A H 0.1730 0.8414 0.2956 0.052 Uiso 1 1 d R U . . .
H10B H 0.2199 0.8851 0.3385 0.052 Uiso 1 1 d R U . . .
H10C H 0.1839 0.7885 0.3713 0.052 Uiso 1 1 d R U . . .
C1 C 0.12163(7) 0.3633(2) 0.24883(10) 0.0216(4) Uani 1 1 d . . . . .
C20 C 0.12161(9) 0.8696(3) 0.17207(13) 0.0330(5) Uani 1 1 d . . . . .
C9 C 0.24240(11) 0.7125(4) 0.23896(16) 0.0489(8) Uani 1 1 d . . . . .
H9A H 0.2624 0.6357 0.2288 0.059 Uiso 1 1 d R U . . .
H9B H 0.2604 0.7982 0.2447 0.059 Uiso 1 1 d R U . . .
H9C H 0.2181 0.7240 0.2020 0.059 Uiso 1 1 d R U . . .
C17 C 0.07913(8) 0.7040(3) 0.27365(12) 0.0272(5) Uani 1 1 d . . . . .
C19 C 0.07351(9) 0.7260(3) 0.06572(13) 0.0329(5) Uani 1 1 d . . . . .
C11 C 0.25838(10) 0.6302(4) 0.36051(19) 0.0557(9) Uani 1 1 d . . . . .
H11A H 0.2452 0.6253 0.4034 0.067 Uiso 1 1 d R U . . .
H11B H 0.2840 0.6960 0.3643 0.067 Uiso 1 1 d R U . . .
H11C H 0.2695 0.5381 0.3491 0.067 Uiso 1 1 d R U . . .
C14 C 0.12954(11) 0.3760(4) 0.00660(14) 0.0554(9) Uani 1 1 d . . . . .
H14A H 0.1304 0.4723 0.0224 0.067 Uiso 1 1 d R U . . .
H14B H 0.1234 0.3746 -0.0424 0.067 Uiso 1 1 d R U . . .
H14C H 0.1591 0.3314 0.0200 0.067 Uiso 1 1 d R U . . .
O3 O 0.07314(8) 0.7463(3) 0.00821(10) 0.0533(6) Uani 1 1 d . . . . .
O2 O -0.00066(7) 0.4598(2) 0.16324(11) 0.0426(5) Uani 1 1 d . . . . .
N1 N 0.18427(6) 0.5687(2) 0.28806(9) 0.0239(4) Uani 1 1 d . . . . .
C13 C 0.09145(9) 0.2958(3) 0.03781(11) 0.0312(5) Uani 1 1 d . . . . .
O5 O -0.00494(6) 0.9364(2) 0.15763(10) 0.0411(4) Uani 1 1 d . . . . .
C21 C 0.02425(8) 0.8524(3) 0.16265(12) 0.0272(5) Uani 1 1 d . . . . .
C18 C 0.02621(8) 0.5475(3) 0.16410(12) 0.0285(5) Uani 1 1 d . . . . .
C6 C 0.09105(8) 0.2533(2) 0.22756(11) 0.0250(5) Uani 1 1 d . . . . .
C5 C 0.07403(9) 0.1651(3) 0.27611(12) 0.0333(5) Uani 1 1 d . . . . .
H5 H 0.0534 0.0921 0.2622 0.040 Uiso 1 1 d R U . . .
C15 C 0.04430(11) 0.3547(4) 0.01153(15) 0.0572(9) Uani 1 1 d . . . . .
H15A H 0.0202 0.3012 0.0302 0.069 Uiso 1 1 d R U . . .
H15B H 0.0402 0.3485 -0.0375 0.069 Uiso 1 1 d R U . . .
H15C H 0.0424 0.4520 0.0252 0.069 Uiso 1 1 d R U . . .
C8 C 0.22089(8) 0.6797(3) 0.30451(13) 0.0313(5) Uani 1 1 d . . . . .
C16 C 0.0944(2) 0.1397(4) 0.02039(16) 0.0885(16) Uani 1 1 d . . . . .
H16A H 0.1213 0.0994 0.0465 0.106 Uiso 1 1 d R U . . .
H16B H 0.0975 0.1299 -0.0276 0.106 Uiso 1 1 d R U . . .
H16C H 0.0667 0.0913 0.0311 0.106 Uiso 1 1 d R U . . .
C4 C 0.08808(10) 0.1849(3) 0.34528(13) 0.0386(6) Uani 1 1 d . . . . .
H4 H 0.0757 0.1279 0.3776 0.046 Uiso 1 1 d R U . . .
C7 C 0.17126(8) 0.4891(2) 0.33552(11) 0.0257(5) Uani 1 1 d . . . . .
H7 H 0.1838 0.5019 0.3807 0.031 Uiso 1 1 d R U . . .


_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
Sb1 C1 2.084(2) . ?
Sb1 N2 2.4212(19) . ?
Sb1 N1 2.4350(18) . ?
Sb1 Mo1 2.8917(2) . ?
Mo1 C21 1.966(2) . ?
Mo1 C20 2.019(3) . ?
Mo1 C19 2.020(2) . ?
Mo1 C17 2.055(2) . ?
Mo1 C18 2.068(3) . ?
O1 C17 1.133(3) . ?
N2 C12 1.283(3) . ?
N2 C13 1.496(3) . ?
C3 C4 1.378(4) . ?
C3 C2 1.400(3) . ?
C3 H3 0.9301 . ?
C12 C6 1.444(3) . ?
C12 H12 0.9300 . ?
C2 C1 1.393(3) . ?
C2 C7 1.444(3) . ?
O4 C20 1.137(3) . ?
C10 C8 1.520(4) . ?
C10 H10A 0.9599 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9602 . ?
C1 C6 1.395(3) . ?
C9 C8 1.517(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9599 . ?
C9 H9C 0.9601 . ?
C19 O3 1.144(3) . ?
C11 C8 1.529(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9601 . ?
C11 H11C 0.9600 . ?
C14 C13 1.513(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O2 C18 1.131(3) . ?
N1 C7 1.283(3) . ?
N1 C8 1.497(3) . ?
C13 C15 1.505(4) . ?
C13 C16 1.517(4) . ?
O5 C21 1.151(3) . ?
C6 C5 1.393(3) . ?
C5 C4 1.388(3) . ?
C5 H5 0.9301 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9599 . ?
C15 H15C 0.9601 . ?
C16 H16A 0.9599 . ?
C16 H16B 0.9601 . ?
C16 H16C 0.9600 . ?
C4 H4 0.9301 . ?
C7 H7 0.9301 . ?

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
C1 Sb1 N2 73.16(7) . . ?
C1 Sb1 N1 72.97(7) . . ?
N2 Sb1 N1 145.64(6) . . ?
C1 Sb1 Mo1 99.03(6) . . ?
N2 Sb1 Mo1 95.14(4) . . ?
N1 Sb1 Mo1 95.66(4) . . ?
C21 Mo1 C20 88.85(10) . . ?
C21 Mo1 C19 87.61(10) . . ?
C20 Mo1 C19 85.35(11) . . ?
C21 Mo1 C17 92.71(9) . . ?
C20 Mo1 C17 90.86(10) . . ?
C19 Mo1 C17 176.19(10) . . ?
C21 Mo1 C18 91.03(9) . . ?
C20 Mo1 C18 179.58(10) . . ?
C19 Mo1 C18 94.24(10) . . ?
C17 Mo1 C18 89.55(9) . . ?
C21 Mo1 Sb1 178.67(7) . . ?
C20 Mo1 Sb1 92.46(7) . . ?
C19 Mo1 Sb1 92.26(7) . . ?
C17 Mo1 Sb1 87.51(6) . . ?
C18 Mo1 Sb1 87.66(7) . . ?
C12 N2 C13 120.4(2) . . ?
C12 N2 Sb1 111.05(14) . . ?
C13 N2 Sb1 128.47(15) . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 119.9 . . ?
N2 C12 C6 119.3(2) . . ?
N2 C12 H12 120.4 . . ?
C6 C12 H12 120.3 . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 C7 116.6(2) . . ?
C3 C2 C7 123.7(2) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.4 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C1 C6 120.0(2) . . ?
C2 C1 Sb1 120.12(16) . . ?
C6 C1 Sb1 119.86(15) . . ?
O4 C20 Mo1 176.2(2) . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.6 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C17 Mo1 179.5(2) . . ?
O3 C19 Mo1 174.6(3) . . ?
C8 C11 H11A 109.3 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.6 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C14 H14A 109.8 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.1 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 N1 C8 120.37(19) . . ?
C7 N1 Sb1 110.81(15) . . ?
C8 N1 Sb1 128.62(14) . . ?
N2 C13 C15 108.6(2) . . ?
N2 C13 C14 107.1(2) . . ?
C15 C13 C14 109.9(3) . . ?
N2 C13 C16 111.0(2) . . ?
C15 C13 C16 110.6(3) . . ?
C14 C13 C16 109.6(3) . . ?
O5 C21 Mo1 178.3(2) . . ?
O2 C18 Mo1 178.1(2) . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 C12 123.7(2) . . ?
C1 C6 C12 116.5(2) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 120.0 . . ?
C13 C15 H15A 109.6 . . ?
C13 C15 H15B 109.4 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.4 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C8 C9 107.5(2) . . ?
N1 C8 C10 108.2(2) . . ?
C9 C8 C10 110.3(2) . . ?
N1 C8 C11 111.5(2) . . ?
C9 C8 C11 110.7(2) . . ?
C10 C8 C11 108.7(2) . . ?
C13 C16 H16A 109.0 . . ?
C13 C16 H16B 109.1 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 110.3 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.8 . . ?
N1 C7 C2 119.4(2) . . ?
N1 C7 H7 120.2 . . ?
C2 C7 H7 120.4 . . ?

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.250 0.500 190 32 ' '
2 0.250 -0.250 1.000 190 32 ' '
3 0.750 0.250 0.000 190 32 ' '
4 0.750 -0.250 0.500 190 32 ' '
_platon_squeeze_details          ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1515230'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C21 H23 Bi N2 O5 W), C7 H8'
_chemical_formula_sum            'C49 H54 Bi2 N4 O10 W2'
_chemical_formula_weight         1644.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
W W -0.8490 6.8722 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   19.4793(16)
_cell_length_b                   19.4789(13)
_cell_length_c                   13.5431(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5138.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    21550
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3080
_exptl_absorpt_coefficient_mu    11.349
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.175
0 -1 0 0.193
0 0 -1 0.080
-1 0 1 0.121
1 0 1 0.058
1 0 0 0.077
-1 0 0 0.149
-1 0 -1 0.127


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.113
_exptl_absorpt_correction_T_max  0.211
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21522
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.40
_reflns_number_total             11091
_reflns_number_gt                10306
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0433P)²+65.0873P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         11091
_refine_ls_number_parameters     604
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.57962(2) 0.15092(2) 1.07868(3) 0.01875(9) Uani 1 1 d . . .
Bi2 Bi 0.76724(2) 0.35293(2) 1.42893(3) 0.02157(10) Uani 1 1 d . . .
W2 W 0.75648(2) 0.33696(2) 1.64458(3) 0.01808(10) Uani 1 1 d . . .
W1 W 0.59303(2) 0.14737(2) 0.86301(3) 0.01864(10) Uani 1 1 d . . .
N1 N 0.5232(5) 0.2676(5) 1.0869(8) 0.020(2) Uani 1 1 d . . .
C21 C 0.5957(6) 0.0443(7) 0.8655(11) 0.028(3) Uani 1 1 d . . .
C19 C 0.5866(6) 0.2524(6) 0.8653(10) 0.023(2) Uani 1 1 d . . .
O3 O 0.5823(5) 0.3109(5) 0.8648(9) 0.036(2) Uani 1 1 d . . .
N3 N 0.6454(6) 0.4037(5) 1.4071(8) 0.026(2) Uani 1 1 d . . .
O2 O 0.4319(5) 0.1389(6) 0.8365(8) 0.036(2) Uani 1 1 d . . .
N2 N 0.6958(6) 0.0925(5) 1.1120(8) 0.025(2) Uani 1 1 d . . .
N4 N 0.8323(5) 0.2437(6) 1.4051(8) 0.025(2) Uani 1 1 d . . .
O4 O 0.7543(4) 0.1546(5) 0.8950(7) 0.035(2) Uani 1 1 d . . .
O8 O 0.9177(4) 0.3452(6) 1.6751(7) 0.035(2) Uani 1 1 d . . .
C120 C 0.7654(6) 0.2328(6) 1.6317(10) 0.025(2) Uani 1 1 d . . .
C117 C 0.7452(5) 0.3275(6) 1.7904(11) 0.025(3) Uani 1 1 d . . .
C101 C 0.6953(6) 0.2701(7) 1.3944(10) 0.028(3) Uani 1 1 d . . .
C5 C 0.7750(6) 0.2624(7) 1.1362(10) 0.027(2) Uani 1 1 d . . .
H5 H 0.8208 0.2509 1.1459 0.032 Uiso 1 1 d R . .
C20 C 0.6951(5) 0.1520(6) 0.8833(8) 0.019(2) Uani 1 1 d . . .
C18 C 0.4900(6) 0.1422(6) 0.8475(9) 0.024(2) Uani 1 1 d . . .
C1 C 0.6581(5) 0.2295(6) 1.1060(8) 0.014(2) Uani 1 1 d . . .
C121 C 0.6528(6) 0.3267(6) 1.6237(10) 0.026(3) Uani 1 1 d . . .
C12 C 0.7428(6) 0.1370(6) 1.1253(8) 0.020(2) Uani 1 1 d . . .
H12 H 0.7872 0.1229 1.1408 0.024 Uiso 1 1 d R . .
C119 C 0.8585(6) 0.3423(6) 1.6613(10) 0.026(3) Uani 1 1 d . . .
C8 C 0.4482(6) 0.2846(7) 1.0846(10) 0.025(3) Uani 1 1 d . . .
C6 C 0.7267(6) 0.2096(6) 1.1195(8) 0.019(2) Uani 1 1 d . . .
C118 C 0.7493(6) 0.4405(6) 1.6557(9) 0.023(2) Uani 1 1 d . . .
C7 C 0.5665(6) 0.3144(5) 1.0997(9) 0.019(2) Uani 1 1 d . . .
H7 H 0.5517 0.3598 1.1037 0.023 Uiso 1 1 d R . .
O9 O 0.7733(5) 0.1761(5) 1.6229(9) 0.040(2) Uani 1 1 d . . .
C10 C 0.4282(7) 0.3193(9) 1.1819(12) 0.037(4) Uani 1 1 d . . .
H10A H 0.4454 0.2926 1.2362 0.044 Uiso 1 1 d R . .
H10B H 0.3792 0.3225 1.1864 0.044 Uiso 1 1 d R . .
H10C H 0.4478 0.3645 1.1841 0.044 Uiso 1 1 d R . .
C106 C 0.7192(7) 0.2032(7) 1.3839(10) 0.027(3) Uani 1 1 d . . .
C17 C 0.6061(5) 0.1475(7) 0.7211(10) 0.026(2) Uani 1 1 d . . .
C113 C 0.9079(6) 0.2332(7) 1.4057(9) 0.026(3) Uani 1 1 d . . .
C2 C 0.6397(5) 0.2984(6) 1.1082(9) 0.020(2) Uani 1 1 d . . .
C104 C 0.6028(7) 0.1643(8) 1.3557(13) 0.039(3) Uani 1 1 d . . .
H104 H 0.5719 0.1286 1.3452 0.047 Uiso 1 1 d R . .
C116 C 0.9305(7) 0.1997(7) 1.3086(10) 0.026(3) Uani 1 1 d . . .
H116A H 0.9006 0.1621 1.2926 0.032 Uiso 1 1 d R . .
H116B H 0.9767 0.1832 1.3147 0.032 Uiso 1 1 d R . .
H116C H 0.9283 0.2335 1.2571 0.032 Uiso 1 1 d R . .
C107 C 0.6032(6) 0.3562(8) 1.3845(9) 0.030(3) Uani 1 1 d . . .
H107 H 0.5575 0.3665 1.3713 0.036 Uiso 1 1 d R . .
C4 C 0.7572(6) 0.3293(6) 1.1379(9) 0.028(3) Uani 1 1 d . . .
H4 H 0.7911 0.3622 1.1484 0.034 Uiso 1 1 d R . .
C112 C 0.7932(6) 0.1918(7) 1.3911(9) 0.023(2) Uani 1 1 d . . .
H112 H 0.8121 0.1482 1.3850 0.028 Uiso 1 1 d R . .
C3 C 0.6895(6) 0.3491(7) 1.1242(9) 0.026(2) Uani 1 1 d . . .
H3 H 0.6774 0.3952 1.1266 0.032 Uiso 1 1 d R . .
C105 C 0.6710(6) 0.1502(7) 1.3665(8) 0.025(2) Uani 1 1 d . . .
H105 H 0.6862 0.1051 1.3613 0.030 Uiso 1 1 d R . .
C115 C 0.9283(8) 0.1866(8) 1.4915(11) 0.036(3) Uani 1 1 d . . .
H115A H 0.9057 0.2019 1.5506 0.043 Uiso 1 1 d R . .
H115B H 0.9771 0.1885 1.5007 0.043 Uiso 1 1 d R . .
H115C H 0.9148 0.1402 1.4774 0.043 Uiso 1 1 d R . .
C114 C 0.9431(6) 0.3028(7) 1.4192(11) 0.031(3) Uani 1 1 d . . .
H114A H 0.9244 0.3351 1.3729 0.037 Uiso 1 1 d R . .
H114B H 0.9914 0.2976 1.4076 0.037 Uiso 1 1 d R . .
H114C H 0.9358 0.3193 1.4852 0.037 Uiso 1 1 d R . .
C11 C 0.4084(6) 0.2177(8) 1.0765(13) 0.038(3) Uani 1 1 d . . .
H11A H 0.4181 0.1893 1.1327 0.046 Uiso 1 1 d R . .
H11B H 0.4225 0.1944 1.0173 0.046 Uiso 1 1 d R . .
H11C H 0.3601 0.2269 1.0735 0.046 Uiso 1 1 d R . .
C9 C 0.4332(7) 0.3293(7) 0.9966(10) 0.032(3) Uani 1 1 d . . .
H9A H 0.3844 0.3350 0.9904 0.038 Uiso 1 1 d R . .
H9B H 0.4508 0.3073 0.9385 0.038 Uiso 1 1 d R . .
H9C H 0.4545 0.3734 1.0043 0.038 Uiso 1 1 d R . .
O1 O 0.6158(4) 0.1484(6) 0.6336(6) 0.035(2) Uani 1 1 d . . .
O6 O 0.7385(4) 0.3221(5) 1.8737(7) 0.030(2) Uani 1 1 d . . .
O7 O 0.7448(6) 0.4984(5) 1.6660(9) 0.042(3) Uani 1 1 d . . .
O5 O 0.5958(6) -0.0157(5) 0.8638(9) 0.040(2) Uani 1 1 d . . .
O10 O 0.5964(4) 0.3183(6) 1.6113(8) 0.035(2) Uani 1 1 d . . .
C103 C 0.5789(7) 0.2328(7) 1.3597(11) 0.032(3) Uani 1 1 d . . .
H103 H 0.5325 0.2425 1.3515 0.039 Uiso 1 1 d R . .
C102 C 0.6258(6) 0.2857(6) 1.3795(9) 0.024(2) Uani 1 1 d . . .
C16 C 0.7599(11) 0.0009(7) 1.2058(12) 0.044(4) Uani 1 1 d . . .
H16A H 0.8055 0.0159 1.1900 0.053 Uiso 1 1 d R . .
H16B H 0.7600 -0.0479 1.2164 0.053 Uiso 1 1 d R . .
H16C H 0.7446 0.0236 1.2647 0.053 Uiso 1 1 d R . .
C14 C 0.7456(9) -0.0047(7) 1.0223(13) 0.039(4) Uani 1 1 d . . .
H14A H 0.7162 0.0064 0.9677 0.047 Uiso 1 1 d R . .
H14B H 0.7526 -0.0534 1.0247 0.047 Uiso 1 1 d R . .
H14C H 0.7890 0.0180 1.0142 0.047 Uiso 1 1 d R . .
C108 C 0.6223(7) 0.4771(7) 1.4118(11) 0.034(3) Uani 1 1 d . . .
C109 C 0.6859(9) 0.5219(7) 1.4201(13) 0.044(4) Uani 1 1 d . . .
H109A H 0.7098 0.5105 1.4799 0.053 Uiso 1 1 d R . .
H109B H 0.6725 0.5693 1.4219 0.053 Uiso 1 1 d R . .
H109C H 0.7154 0.5141 1.3645 0.053 Uiso 1 1 d R . .
C13 C 0.7112(7) 0.0184(7) 1.1189(11) 0.032(3) Uani 1 1 d . . .
C15 C 0.6437(8) -0.0179(7) 1.1335(15) 0.044(4) Uani 1 1 d . . .
H15A H 0.6199 -0.0003 1.1902 0.053 Uiso 1 1 d R . .
H15B H 0.6524 -0.0660 1.1425 0.053 Uiso 1 1 d R . .
H15C H 0.6160 -0.0112 1.0757 0.053 Uiso 1 1 d R . .
C111 C 0.5785(11) 0.4854(9) 1.5046(18) 0.059(6) Uani 1 1 d . . .
H111A H 0.5331 0.4682 1.4925 0.071 Uiso 1 1 d R . .
H111B H 0.5760 0.5329 1.5232 0.071 Uiso 1 1 d R . .
H111C H 0.5994 0.4595 1.5569 0.071 Uiso 1 1 d R . .
C24 C 0.0795(9) -0.0034(8) 0.9628(18) 0.051(5) Uani 1 1 d . . .
H24 H 0.1130 -0.0044 0.9140 0.061 Uiso 1 1 d R . .
C27 C -0.0148(10) -0.0065(8) 1.1080(13) 0.045(4) Uani 1 1 d . . .
H27 H -0.0479 -0.0028 1.1572 0.054 Uiso 1 1 d R . .
C25 C 0.0146(10) -0.0219(9) 0.9371(17) 0.054(4) Uani 1 1 d . . .
H25 H 0.0025 -0.0305 0.8718 0.065 Uiso 1 1 d R . .
C22 C 0.0530(9) 0.0119(8) 1.1248(15) 0.045(4) Uani 1 1 d . . .
C26 C -0.0330(10) -0.0251(10) 1.0142(16) 0.057(5) Uani 1 1 d . . .
H26 H -0.0768 -0.0426 1.0027 0.068 Uiso 1 1 d R . .
C23 C 0.0995(11) 0.0166(10) 1.0526(17) 0.056(5) Uani 1 1 d . . .
H23 H 0.1436 0.0333 1.0630 0.068 Uiso 1 1 d R . .
C110 C 0.5827(12) 0.4978(12) 1.3192(17) 0.067(7) Uani 1 1 d . . .
H110A H 0.6130 0.4980 1.2633 0.081 Uiso 1 1 d R . .
H110B H 0.5647 0.5432 1.3293 0.081 Uiso 1 1 d R . .
H110C H 0.5456 0.4665 1.3075 0.081 Uiso 1 1 d R . .
C28 C 0.0728(14) 0.0309(14) 1.2309(16) 0.076(7) Uani 1 1 d . . .
H28A H 0.1164 0.0108 1.2470 0.092 Uiso 1 1 d R . .
H28B H 0.0385 0.0143 1.2760 0.092 Uiso 1 1 d R . .
H28C H 0.0759 0.0800 1.2360 0.092 Uiso 1 1 d R . .


_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
Bi1 C1 2.195(10) . ?
Bi1 N1 2.526(10) . ?
Bi1 N2 2.573(10) . ?
Bi1 W1 2.9334(7) . ?
Bi2 C101 2.187(14) . ?
Bi2 N4 2.497(11) . ?
Bi2 N3 2.588(11) . ?
Bi2 W2 2.9446(7) . ?
W2 C117 1.996(15) . ?
W2 C119 2.003(12) . ?
W2 C118 2.028(11) . ?
W2 C120 2.043(12) . ?
W2 C121 2.050(12) . ?
W1 C17 1.939(14) . ?
W1 C21 2.008(13) . ?
W1 C20 2.010(10) . ?
W1 C18 2.020(12) . ?
W1 C19 2.051(11) . ?
N1 C7 1.255(14) . ?
N1 C8 1.499(14) . ?
C21 O5 1.170(16) . ?
C19 O3 1.142(15) . ?
N3 C107 1.276(18) . ?
N3 C108 1.500(17) . ?
O2 C18 1.144(15) . ?
N2 C12 1.274(16) . ?
N2 C13 1.477(15) . ?
N4 C112 1.280(16) . ?
N4 C113 1.488(15) . ?
O4 C20 1.165(13) . ?
O8 C119 1.168(15) . ?
C120 O9 1.123(16) . ?
C117 O6 1.140(17) . ?
C101 C106 1.392(19) . ?
C101 C102 1.403(17) . ?
C5 C4 1.348(18) . ?
C5 C6 1.412(17) . ?
C5 H5 0.9299 . ?
C1 C2 1.388(16) . ?
C1 C6 1.404(15) . ?
C121 O10 1.122(15) . ?
C12 C6 1.451(15) . ?
C12 H12 0.9300 . ?
C8 C9 1.504(18) . ?
C8 C11 1.520(19) . ?
C8 C10 1.532(19) . ?
C118 O7 1.140(15) . ?
C7 C2 1.464(14) . ?
C7 H7 0.9301 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9601 . ?
C10 H10C 0.9600 . ?
C106 C105 1.415(17) . ?
C106 C112 1.460(17) . ?
C17 O1 1.200(17) . ?
C113 C115 1.528(19) . ?
C113 C114 1.531(19) . ?
C113 C116 1.533(17) . ?
C2 C3 1.401(16) . ?
C104 C105 1.365(18) . ?
C104 C103 1.41(2) . ?
C104 H104 0.9301 . ?
C116 H116A 0.9599 . ?
C116 H116B 0.9601 . ?
C116 H116C 0.9601 . ?
C107 C102 1.443(19) . ?
C107 H107 0.9299 . ?
C4 C3 1.387(17) . ?
C4 H4 0.9301 . ?
C112 H112 0.9300 . ?
C3 H3 0.9301 . ?
C105 H105 0.9299 . ?
C115 H115A 0.9600 . ?
C115 H115B 0.9600 . ?
C115 H115C 0.9601 . ?
C114 H114A 0.9600 . ?
C114 H114B 0.9601 . ?
C114 H114C 0.9599 . ?
C11 H11A 0.9599 . ?
C11 H11B 0.9599 . ?
C11 H11C 0.9601 . ?
C9 H9A 0.9599 . ?
C9 H9B 0.9599 . ?
C9 H9C 0.9599 . ?
C103 C102 1.402(18) . ?
C103 H103 0.9298 . ?
C16 C13 1.55(2) . ?
C16 H16A 0.9599 . ?
C16 H16B 0.9601 . ?
C16 H16C 0.9601 . ?
C14 C13 1.54(2) . ?
C14 H14A 0.9601 . ?
C14 H14B 0.9601 . ?
C14 H14C 0.9598 . ?
C108 C109 1.52(2) . ?
C108 C110 1.53(2) . ?
C108 C111 1.53(2) . ?
C109 H109A 0.9600 . ?
C109 H109B 0.9602 . ?
C109 H109C 0.9599 . ?
C13 C15 1.51(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C111 H111A 0.9599 . ?
C111 H111B 0.9600 . ?
C111 H111C 0.9600 . ?
C24 C23 1.33(3) . ?
C24 C25 1.36(2) . ?
C24 H24 0.9300 . ?
C27 C26 1.37(3) . ?
C27 C22 1.39(2) . ?
C27 H27 0.9300 . ?
C25 C26 1.40(3) . ?
C25 H25 0.9299 . ?
C22 C23 1.34(3) . ?
C22 C28 1.53(3) . ?
C26 H26 0.9299 . ?
C23 H23 0.9301 . ?
C110 H110A 0.9599 . ?
C110 H110B 0.9600 . ?
C110 H110C 0.9600 . ?
C28 H28A 0.9599 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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
C1 Bi1 N1 70.6(4) . . ?
C1 Bi1 N2 70.5(4) . . ?
N1 Bi1 N2 140.6(3) . . ?
C1 Bi1 W1 97.0(3) . . ?
N1 Bi1 W1 96.0(2) . . ?
N2 Bi1 W1 94.9(2) . . ?
C101 Bi2 N4 70.7(4) . . ?
C101 Bi2 N3 70.7(4) . . ?
N4 Bi2 N3 140.9(3) . . ?
C101 Bi2 W2 95.1(3) . . ?
N4 Bi2 W2 94.2(2) . . ?
N3 Bi2 W2 95.1(2) . . ?
C117 W2 C119 90.1(5) . . ?
C117 W2 C118 90.6(5) . . ?
C119 W2 C118 90.5(5) . . ?
C117 W2 C120 90.1(5) . . ?
C119 W2 C120 88.7(5) . . ?
C118 W2 C120 178.9(5) . . ?
C117 W2 C121 91.1(5) . . ?
C119 W2 C121 177.0(5) . . ?
C118 W2 C121 92.3(5) . . ?
C120 W2 C121 88.5(5) . . ?
C117 W2 Bi2 177.6(3) . . ?
C119 W2 Bi2 92.1(4) . . ?
C118 W2 Bi2 88.5(4) . . ?
C120 W2 Bi2 90.8(4) . . ?
C121 W2 Bi2 86.8(4) . . ?
C17 W1 C21 90.8(6) . . ?
C17 W1 C20 90.3(4) . . ?
C21 W1 C20 91.0(5) . . ?
C17 W1 C18 91.6(5) . . ?
C21 W1 C18 88.7(5) . . ?
C20 W1 C18 178.1(5) . . ?
C17 W1 C19 91.2(5) . . ?
C21 W1 C19 177.2(5) . . ?
C20 W1 C19 90.8(5) . . ?
C18 W1 C19 89.5(5) . . ?
C17 W1 Bi1 177.2(3) . . ?
C21 W1 Bi1 90.5(4) . . ?
C20 W1 Bi1 87.2(3) . . ?
C18 W1 Bi1 90.9(4) . . ?
C19 W1 Bi1 87.5(4) . . ?
C7 N1 C8 119.8(10) . . ?
C7 N1 Bi1 111.6(7) . . ?
C8 N1 Bi1 128.5(7) . . ?
O5 C21 W1 177.5(13) . . ?
O3 C19 W1 178.6(13) . . ?
C107 N3 C108 120.6(11) . . ?
C107 N3 Bi2 109.9(8) . . ?
C108 N3 Bi2 129.4(8) . . ?
C12 N2 C13 120.6(11) . . ?
C12 N2 Bi1 110.9(7) . . ?
C13 N2 Bi1 128.5(8) . . ?
C112 N4 C113 118.8(11) . . ?
C112 N4 Bi2 113.0(8) . . ?
C113 N4 Bi2 128.3(8) . . ?
O9 C120 W2 176.7(11) . . ?
O6 C117 W2 179.7(12) . . ?
C106 C101 C102 120.7(12) . . ?
C106 C101 Bi2 119.9(9) . . ?
C102 C101 Bi2 119.4(10) . . ?
C4 C5 C6 122.5(11) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 119.0 . . ?
O4 C20 W1 179.9(12) . . ?
O2 C18 W1 178.4(12) . . ?
C2 C1 C6 120.7(10) . . ?
C2 C1 Bi1 119.8(8) . . ?
C6 C1 Bi1 119.5(8) . . ?
O10 C121 W2 177.1(11) . . ?
N2 C12 C6 120.0(10) . . ?
N2 C12 H12 120.0 . . ?
C6 C12 H12 120.0 . . ?
O8 C119 W2 177.3(11) . . ?
N1 C8 C9 109.6(10) . . ?
N1 C8 C11 108.0(10) . . ?
C9 C8 C11 109.8(12) . . ?
N1 C8 C10 109.1(11) . . ?
C9 C8 C10 112.2(11) . . ?
C11 C8 C10 108.1(12) . . ?
C1 C6 C5 116.9(10) . . ?
C1 C6 C12 118.8(10) . . ?
C5 C6 C12 124.0(10) . . ?
O7 C118 W2 177.2(12) . . ?
N1 C7 C2 120.6(10) . . ?
N1 C7 H7 119.4 . . ?
C2 C7 H7 120.0 . . ?
C8 C10 H10A 109.4 . . ?
C8 C10 H10B 109.7 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.3 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C101 C106 C105 118.6(12) . . ?
C101 C106 C112 117.8(11) . . ?
C105 C106 C112 123.7(12) . . ?
O1 C17 W1 178.3(10) . . ?
N4 C113 C115 110.1(11) . . ?
N4 C113 C114 108.8(11) . . ?
C115 C113 C114 108.6(11) . . ?
N4 C113 C116 109.8(10) . . ?
C115 C113 C116 109.0(11) . . ?
C114 C113 C116 110.6(11) . . ?
C1 C2 C3 120.3(10) . . ?
C1 C2 C7 117.2(10) . . ?
C3 C2 C7 122.4(11) . . ?
C105 C104 C103 120.4(12) . . ?
C105 C104 H104 119.7 . . ?
C103 C104 H104 119.8 . . ?
C113 C116 H116A 110.2 . . ?
C113 C116 H116B 109.7 . . ?
H116A C116 H116B 109.5 . . ?
C113 C116 H116C 108.5 . . ?
H116A C116 H116C 109.5 . . ?
H116B C116 H116C 109.5 . . ?
N3 C107 C102 120.4(11) . . ?
N3 C107 H107 120.3 . . ?
C102 C107 H107 119.2 . . ?
C5 C4 C3 120.7(11) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 120.3 . . ?
N4 C112 C106 118.5(12) . . ?
N4 C112 H112 119.9 . . ?
C106 C112 H112 121.6 . . ?
C4 C3 C2 118.9(11) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.8 . . ?
C104 C105 C106 121.2(12) . . ?
C104 C105 H105 119.4 . . ?
C106 C105 H105 119.4 . . ?
C113 C115 H115A 109.3 . . ?
C113 C115 H115B 109.4 . . ?
H115A C115 H115B 109.5 . . ?
C113 C115 H115C 109.7 . . ?
H115A C115 H115C 109.5 . . ?
H115B C115 H115C 109.5 . . ?
C113 C114 H114A 109.5 . . ?
C113 C114 H114B 109.0 . . ?
H114A C114 H114B 109.5 . . ?
C113 C114 H114C 110.0 . . ?
H114A C114 H114C 109.5 . . ?
H114B C114 H114C 109.5 . . ?
C8 C11 H11A 109.6 . . ?
C8 C11 H11B 108.7 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 110.1 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 110.4 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C102 C103 C104 119.1(12) . . ?
C102 C103 H103 120.3 . . ?
C104 C103 H103 120.6 . . ?
C103 C102 C101 119.9(12) . . ?
C103 C102 C107 120.7(12) . . ?
C101 C102 C107 119.5(12) . . ?
C13 C16 H16A 109.2 . . ?
C13 C16 H16B 109.4 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.8 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 110.3 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C108 C109 107.8(11) . . ?
N3 C108 C110 111.6(14) . . ?
C109 C108 C110 108.7(15) . . ?
N3 C108 C111 107.6(12) . . ?
C109 C108 C111 109.5(15) . . ?
C110 C108 C111 111.5(15) . . ?
C108 C109 H109A 109.1 . . ?
C108 C109 H109B 109.4 . . ?
H109A C109 H109B 109.5 . . ?
C108 C109 H109C 109.9 . . ?
H109A C109 H109C 109.5 . . ?
H109B C109 H109C 109.5 . . ?
N2 C13 C15 106.7(11) . . ?
N2 C13 C14 108.7(12) . . ?
C15 C13 C14 110.8(13) . . ?
N2 C13 C16 112.8(11) . . ?
C15 C13 C16 109.4(14) . . ?
C14 C13 C16 108.4(13) . . ?
C13 C15 H15A 111.1 . . ?
C13 C15 H15B 108.6 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 108.7 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C108 C111 H111A 109.7 . . ?
C108 C111 H111B 110.2 . . ?
H111A C111 H111B 109.5 . . ?
C108 C111 H111C 108.4 . . ?
H111A C111 H111C 109.5 . . ?
H111B C111 H111C 109.5 . . ?
C23 C24 C25 126(2) . . ?
C23 C24 H24 116.7 . . ?
C25 C24 H24 117.7 . . ?
C26 C27 C22 118.0(18) . . ?
C26 C27 H27 120.3 . . ?
C22 C27 H27 121.5 . . ?
C24 C25 C26 116(2) . . ?
C24 C25 H25 121.7 . . ?
C26 C25 H25 122.3 . . ?
C23 C22 C27 122.8(19) . . ?
C23 C22 C28 120.0(17) . . ?
C27 C22 C28 117.1(19) . . ?
C27 C26 C25 120.6(17) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.9 . . ?
C24 C23 C22 116.7(19) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 122.6 . . ?
C108 C110 H110A 109.9 . . ?
C108 C110 H110B 108.1 . . ?
H110A C110 H110B 109.5 . . ?
C108 C110 H110C 110.4 . . ?
H110A C110 H110C 109.5 . . ?
H110B C110 H110C 109.5 . . ?
C22 C28 H28A 109.6 . . ?
C22 C28 H28B 109.9 . . ?
H28A C28 H28B 109.5 . . ?
C22 C28 H28C 108.9 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.40
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         3.613
_refine_diff_density_min         -2.686
_refine_diff_density_rms         0.270
####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1515231'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 Bi Mo N2 O5'
_chemical_formula_sum            'C21 H23 Bi Mo N2 O5'
_chemical_formula_weight         688.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5700(7)
_cell_length_b                   10.6180(8)
_cell_length_c                   11.4101(8)
_cell_angle_alpha                70.472(7)
_cell_angle_beta                 89.817(7)
_cell_angle_gamma                78.893(6)
_cell_volume                     1181.72(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    25212
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    7.998
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.259
-1 0 1 0.248
-1 -1 -1 0.075
1 1 1 0.064
0 -1 0 0.185
0 1 0 0.232
-1 1 1 0.212
0 0 1 0.217


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.063
_exptl_absorpt_correction_T_max  0.356
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_reflns_number            25088
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0658
_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       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.898
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5402
_reflns_number_gt                5070
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+3.2133P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5402
_refine_ls_number_parameters     295
_refine_ls_number_restraints     352
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0731
_refine_ls_wR_factor_gt          0.0678
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.23768(2) 0.07618(2) -0.15366(2) 0.01800(6) Uani 1 1 d . U . . .
Mo1 Mo 0.31360(4) 0.27117(4) -0.38014(4) 0.02370(9) Uani 1 1 d . U . . .
O3 O 0.0173(3) 0.3446(3) -0.4775(3) 0.0282(7) Uani 1 1 d . U . . .
N1 N 0.0080(3) 0.2091(3) -0.1698(3) 0.0172(6) Uani 1 1 d . U . . .
N2 N 0.3656(3) -0.1372(4) -0.1860(3) 0.0214(7) Uani 1 1 d . U . . .
O4 O 0.3532(4) 0.0267(4) -0.4882(3) 0.0356(8) Uani 1 1 d . U . . .
O2 O 0.2867(5) 0.4951(4) -0.2506(5) 0.0512(11) Uani 1 1 d . U . . .
C7 C -0.0693(4) 0.1641(4) -0.2234(4) 0.0198(7) Uani 1 1 d . U . . .
H7 H -0.1570 0.2032 -0.2348 0.024 Uiso 1 1 d R U . . .
C20 C 0.3402(4) 0.1142(5) -0.4500(4) 0.0274(9) Uani 1 1 d . U . . .
C1 C 0.1108(4) -0.0073(4) -0.2459(4) 0.0172(7) Uani 1 1 d . U . . .
C3 C -0.1018(4) -0.0030(5) -0.3257(4) 0.0250(9) Uani 1 1 d . U . . .
H3 H -0.1889 0.0380 -0.3436 0.030 Uiso 1 1 d R U . . .
C4 C -0.0520(5) -0.1155(5) -0.3591(5) 0.0296(9) Uani 1 1 d . U . . .
H4 H -0.1061 -0.1520 -0.3971 0.035 Uiso 1 1 d R U . . .
C12 C 0.2954(4) -0.1869(4) -0.2427(4) 0.0209(8) Uani 1 1 d . U . . .
H12 H 0.3310 -0.2646 -0.2613 0.025 Uiso 1 1 d R U . . .
C6 C 0.1602(4) -0.1228(4) -0.2772(4) 0.0193(7) Uani 1 1 d . U . . .
C19 C 0.1230(4) 0.3200(4) -0.4419(4) 0.0211(8) Uani 1 1 d . U . . .
C9 C -0.0497(5) 0.4577(4) -0.2262(4) 0.0284(9) Uani 1 1 d . U . . .
H9A H 0.0340 0.4645 -0.2576 0.034 Uiso 1 1 d R U . . .
H9B H -0.0801 0.5314 -0.1956 0.034 Uiso 1 1 d R U . . .
H9C H -0.1090 0.4626 -0.2919 0.034 Uiso 1 1 d R U . . .
C8 C -0.0407(4) 0.3221(4) -0.1205(4) 0.0212(8) Uani 1 1 d . U . . .
C2 C -0.0205(4) 0.0511(4) -0.2675(4) 0.0183(7) Uani 1 1 d . U . . .
C13 C 0.5015(4) -0.2076(4) -0.1403(4) 0.0283(9) Uani 1 1 d D U . . .
C18 C 0.2935(5) 0.4151(5) -0.2976(5) 0.0318(10) Uani 1 1 d . U . . .
C5 C 0.0783(5) -0.1758(4) -0.3352(4) 0.0257(9) Uani 1 1 d . U . . .
H5 H 0.1114 -0.2513 -0.3581 0.031 Uiso 1 1 d R U . . .
C10 C 0.0575(5) 0.3077(5) -0.0173(5) 0.0346(11) Uani 1 1 d . U . . .
H10A H 0.0681 0.2187 0.0450 0.042 Uiso 1 1 d R U . . .
H10B H 0.0287 0.3759 0.0203 0.042 Uiso 1 1 d R U . . .
H10C H 0.1385 0.3200 -0.0529 0.042 Uiso 1 1 d R U . . .
C11 C -0.1728(5) 0.3137(5) -0.0679(5) 0.0328(10) Uani 1 1 d . U . . .
H11A H -0.2332 0.3180 -0.1325 0.039 Uiso 1 1 d R U . . .
H11B H -0.2016 0.3886 -0.0385 0.039 Uiso 1 1 d R U . . .
H11C H -0.1669 0.2292 -0.0002 0.039 Uiso 1 1 d R U . . .
C21 C 0.4993(9) 0.2447(12) -0.3336(13) 0.0300(19) Uani 0.532(9) 1 d D U P A 1
C17 C 0.3506(19) 0.4099(19) -0.5352(17) 0.046(3) Uani 0.67(3) 1 d D U P A 1
O1 O 0.3715(18) 0.4946(15) -0.6241(9) 0.062(3) Uani 0.67(3) 1 d D U P A 1
O5 O 0.6070(7) 0.2306(10) -0.3083(10) 0.0468(17) Uani 0.532(9) 1 d D U P A 1
C14 C 0.5835(8) -0.0911(8) -0.1774(8) 0.0315(13) Uani 0.562(6) 1 d D U P B 1
H14A H 0.5834 -0.0537 -0.2665 0.047 Uiso 0.562(6) 1 calc R U P B 1
H14B H 0.6707 -0.1289 -0.1426 0.047 Uiso 0.562(6) 1 calc R U P B 1
H14C H 0.5459 -0.0204 -0.1455 0.047 Uiso 0.562(6) 1 calc R U P B 1
C16 C 0.5086(9) -0.2587(10) -0.0018(7) 0.0349(14) Uani 0.562(6) 1 d D U P B 1
H16A H 0.4657 -0.1876 0.0273 0.052 Uiso 0.562(6) 1 calc R U P B 1
H16B H 0.5975 -0.2860 0.0294 0.052 Uiso 0.562(6) 1 calc R U P B 1
H16C H 0.4673 -0.3356 0.0274 0.052 Uiso 0.562(6) 1 calc R U P B 1
C15 C 0.5648(8) -0.3070(8) -0.2008(8) 0.0331(14) Uani 0.562(6) 1 d D U P B 1
H15A H 0.5548 -0.2641 -0.2897 0.050 Uiso 0.562(6) 1 calc R U P B 1
H15B H 0.5251 -0.3851 -0.1768 0.050 Uiso 0.562(6) 1 calc R U P B 1
H15C H 0.6551 -0.3353 -0.1746 0.050 Uiso 0.562(6) 1 calc R U P B 1
C15A C 0.5028(11) -0.3652(8) -0.0854(11) 0.0331(14) Uani 0.438(6) 1 d D U P B 2
H15D H 0.4512 -0.3835 -0.0146 0.050 Uiso 0.438(6) 1 calc R U P B 2
H15E H 0.5900 -0.4147 -0.0604 0.050 Uiso 0.438(6) 1 calc R U P B 2
H15F H 0.4680 -0.3935 -0.1479 0.050 Uiso 0.438(6) 1 calc R U P B 2
C14A C 0.5817(9) -0.1851(12) -0.2472(9) 0.0315(13) Uani 0.438(6) 1 d D U P B 2
H14D H 0.5482 -0.2176 -0.3074 0.047 Uiso 0.438(6) 1 calc R U P B 2
H14E H 0.6688 -0.2337 -0.2200 0.047 Uiso 0.438(6) 1 calc R U P B 2
H14F H 0.5807 -0.0894 -0.2845 0.047 Uiso 0.438(6) 1 calc R U P B 2
C16A C 0.5338(11) -0.1667(13) -0.0335(9) 0.0349(14) Uani 0.438(6) 1 d D U P B 2
H16D H 0.4723 -0.1885 0.0284 0.052 Uiso 0.438(6) 1 calc R U P B 2
H16E H 0.5311 -0.0703 -0.0620 0.052 Uiso 0.438(6) 1 calc R U P B 2
H16F H 0.6189 -0.2149 0.0020 0.052 Uiso 0.438(6) 1 calc R U P B 2
O5A O 0.6069(8) 0.1675(12) -0.2564(12) 0.0468(17) Uani 0.468(9) 1 d D U P A 2
O1A O 0.424(3) 0.453(4) -0.614(2) 0.062(3) Uani 0.33(3) 1 d . U P A 2
C21A C 0.5030(11) 0.1969(14) -0.2990(14) 0.0300(19) Uani 0.468(9) 1 d D U P A 2
C17A C 0.377(5) 0.398(4) -0.536(4) 0.046(3) Uani 0.33(3) 1 d D U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C1 2.188(4) . ?
Bi1 N1 2.536(3) . ?
Bi1 N2 2.544(4) . ?
Bi1 Mo1 2.9426(5) . ?
Mo1 C21 1.977(9) . ?
Mo1 C17 1.982(8) . ?
Mo1 C18 2.026(5) . ?
Mo1 C17A 2.041(18) . ?
Mo1 C19 2.046(4) . ?
Mo1 C20 2.049(5) . ?
Mo1 C21A 2.098(10) . ?
O3 C19 1.141(5) . ?
N1 C7 1.273(5) . ?
N1 C8 1.493(5) . ?
N2 C12 1.277(6) . ?
N2 C13 1.491(5) . ?
O4 C20 1.138(6) . ?
O2 C18 1.138(7) . ?
C7 C2 1.456(6) . ?
C7 H7 0.9300 . ?
C1 C2 1.393(6) . ?
C1 C6 1.396(5) . ?
C3 C4 1.382(6) . ?
C3 C2 1.399(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(7) . ?
C4 H4 0.9299 . ?
C12 C6 1.453(6) . ?
C12 H12 0.9299 . ?
C6 C5 1.394(6) . ?
C9 C8 1.524(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 C10 1.521(6) . ?
C8 C11 1.525(6) . ?
C13 C14A 1.463(8) . ?
C13 C16A 1.484(8) . ?
C13 C16 1.487(7) . ?
C13 C15 1.500(7) . ?
C13 C15A 1.576(8) . ?
C13 C14 1.588(7) . ?
C5 H5 0.9299 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9601 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9601 . ?
C11 H11B 0.9601 . ?
C11 H11C 0.9600 . ?
C21 O5 1.144(8) . ?
C17 O1 1.163(9) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?
C15A H15F 0.9600 . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
O5A C21A 1.145(8) . ?
O1A C17A 1.07(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
C1 Bi1 N1 70.88(13) . . ?
C1 Bi1 N2 70.69(13) . . ?
N1 Bi1 N2 141.08(11) . . ?
C1 Bi1 Mo1 97.30(10) . . ?
N1 Bi1 Mo1 94.82(7) . . ?
N2 Bi1 Mo1 95.93(8) . . ?
C21 Mo1 C17 84.6(7) . . ?
C21 Mo1 C18 83.8(4) . . ?
C17 Mo1 C18 88.3(9) . . ?
C18 Mo1 C17A 91.2(18) . . ?
C21 Mo1 C19 173.5(4) . . ?
C17 Mo1 C19 89.4(6) . . ?
C18 Mo1 C19 93.58(19) . . ?
C17A Mo1 C19 96.6(13) . . ?
C21 Mo1 C20 93.9(4) . . ?
C17 Mo1 C20 95.5(9) . . ?
C18 Mo1 C20 175.3(2) . . ?
C17A Mo1 C20 92.3(18) . . ?
C19 Mo1 C20 89.14(17) . . ?
C18 Mo1 C21A 88.7(5) . . ?
C17A Mo1 C21A 90.8(14) . . ?
C19 Mo1 C21A 172.1(4) . . ?
C20 Mo1 C21A 88.1(4) . . ?
C21 Mo1 Bi1 99.4(4) . . ?
C17 Mo1 Bi1 175.6(6) . . ?
C18 Mo1 Bi1 90.44(14) . . ?
C17A Mo1 Bi1 176.4(13) . . ?
C19 Mo1 Bi1 86.51(11) . . ?
C20 Mo1 Bi1 85.93(13) . . ?
C21A Mo1 Bi1 86.0(4) . . ?
C7 N1 C8 120.9(4) . . ?
C7 N1 Bi1 111.2(3) . . ?
C8 N1 Bi1 127.8(3) . . ?
C12 N2 C13 121.0(4) . . ?
C12 N2 Bi1 111.1(3) . . ?
C13 N2 Bi1 127.7(3) . . ?
N1 C7 C2 120.0(4) . . ?
N1 C7 H7 120.2 . . ?
C2 C7 H7 119.8 . . ?
O4 C20 Mo1 179.0(4) . . ?
C2 C1 C6 120.2(4) . . ?
C2 C1 Bi1 119.7(3) . . ?
C6 C1 Bi1 120.0(3) . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 119.4 . . ?
N2 C12 C6 120.1(4) . . ?
N2 C12 H12 119.7 . . ?
C6 C12 H12 120.1 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 C12 122.4(4) . . ?
C1 C6 C12 118.0(4) . . ?
O3 C19 Mo1 178.2(4) . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.4 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C8 C10 106.5(3) . . ?
N1 C8 C9 108.5(3) . . ?
C10 C8 C9 110.8(4) . . ?
N1 C8 C11 112.1(4) . . ?
C10 C8 C11 109.5(4) . . ?
C9 C8 C11 109.4(4) . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 C7 118.2(4) . . ?
C3 C2 C7 122.1(4) . . ?
C14A C13 C16A 119.9(7) . . ?
C14A C13 N2 108.4(5) . . ?
C16A C13 N2 107.0(5) . . ?
N2 C13 C16 108.2(5) . . ?
N2 C13 C15 116.3(5) . . ?
C16 C13 C15 116.1(6) . . ?
C14A C13 C15A 107.4(7) . . ?
C16A C13 C15A 106.4(7) . . ?
N2 C13 C15A 107.0(5) . . ?
N2 C13 C14 105.6(4) . . ?
C16 C13 C14 105.0(6) . . ?
C15 C13 C14 104.3(6) . . ?
O2 C18 Mo1 177.7(5) . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 119.8 . . ?
C8 C10 H10A 110.0 . . ?
C8 C10 H10B 109.9 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 108.6 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.1 . . ?
C8 C11 H11B 109.8 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.6 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C21 Mo1 179.0(11) . . ?
O1 C17 Mo1 178(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C15A H15D 109.5 . . ?
C13 C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
C13 C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C13 C14A H14D 109.5 . . ?
C13 C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
C13 C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C13 C16A H16D 109.5 . . ?
C13 C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C13 C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
O5A C21A Mo1 174.3(11) . . ?
O1A C17A Mo1 171(4) . . ?

_refine_diff_density_max         1.475
_refine_diff_density_min         -3.047
_refine_diff_density_rms         0.192
####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1515232'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_CHEMW03_1a                  
;
PROBLEM: WARNING: The ratio of given/expected molecular ...  
RESPONSE: The structure contains disordered toluene.
The Platon SQUEEZE program was used.
;
_vrf_CELLZ01_1a                  
;
PROBLEM: WARNING:  Difference between formula and atom_site ...  
RESPONSE: The structure contains disordered toluene.
The Platon SQUEEZE program was used.
;
_vrf_FORMU01_1a                  
;
PROBLEM: WARNING:  Difference between formula and atom_site ...  
RESPONSE: The structure contains disordered toluene.
The Platon SQUEEZE program was used.
;
_vrf_PLAT041_1a                  
;
PROBLEM: WARNING:  Difference between formula and atom_site ...  
RESPONSE: The structure contains disordered toluene.
The Platon SQUEEZE program was used.
;
_vrf_PLAT990_1a                  
;
PROBLEM: WARNING:  Difference between formula and atom_site ...  
RESPONSE: The structure contains disordered toluene.
The Platon SQUEEZE program was used.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 As Cr N2 O5, 0.5(C7 H8)'
_chemical_formula_sum            'C24.50 H27 As Cr N2 O5'
_chemical_formula_weight         556.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   28.0370(3)
_cell_length_b                   9.3332(4)
_cell_length_c                   19.4852(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.871(2)
_cell_angle_gamma                90
_cell_volume                     5072.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    16634
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             2280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.39
_exptl_absorpt_coefficient_mu    1.782
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 0 0.248
-1 -1 0 0.221
-1 0 0 0.146
1 0 0 0.175
0 0 -1 0.111
0 0 1 0.204
0 -1 1 0.249
1 -1 0 0.153
1 0 1 0.178


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.512
_exptl_absorpt_correction_T_max  0.655
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_reflns_number            16519
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.066
_diffrn_reflns_theta_max         26.850
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             5351
_reflns_number_gt                4006
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+54.5372P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5351
_refine_ls_number_parameters     271
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
As1 As 0.14228(2) 0.48064(7) 0.18273(3) 0.0517(2) Uani 1 1 d . . . . .
Cr1 Cr 0.07592(3) 0.68199(9) 0.17218(4) 0.0316(2) Uani 1 1 d . . . . .
O1 O 0.00027(12) 0.9078(4) 0.1588(2) 0.0393(8) Uani 1 1 d . . . . .
N2 N 0.09825(13) 0.3088(4) 0.11500(18) 0.0260(8) Uani 1 1 d . . . . .
N1 N 0.18355(12) 0.5607(4) 0.28613(18) 0.0240(8) Uani 1 1 d . . . . .
O3 O 0.08176(12) 0.6886(4) 0.32874(18) 0.0436(9) Uani 1 1 d . . . . .
C1 C 0.11953(15) 0.3575(5) 0.2488(2) 0.0250(9) Uani 1 1 d . . . . .
O2 O 0.14346(15) 0.9319(6) 0.1717(3) 0.0788(17) Uani 1 1 d . . . . .
O5 O 0.07699(17) 0.7160(5) 0.0187(2) 0.0603(12) Uani 1 1 d . . . . .
C2 C 0.13585(16) 0.3742(5) 0.3188(2) 0.0267(9) Uani 1 1 d . . . . .
O4 O -0.00092(14) 0.4507(5) 0.1644(2) 0.0493(10) Uani 1 1 d . . . . .
C17 C 0.02890(15) 0.8186(5) 0.1650(2) 0.0281(10) Uani 1 1 d . . . . .
C8 C 0.22215(16) 0.6711(5) 0.2995(3) 0.0365(11) Uani 1 1 d . . . . .
C19 C 0.07938(16) 0.6827(6) 0.2703(3) 0.0342(11) Uani 1 1 d . . . . .
C6 C 0.08915(17) 0.2437(5) 0.2291(2) 0.0300(10) Uani 1 1 d . . . . .
C7 C 0.17132(16) 0.4827(5) 0.3352(2) 0.0281(10) Uani 1 1 d . . . . .
H7 H 0.1852 0.4956 0.3802 0.034 Uiso 1 1 d R U . . .
C12 C 0.07945(17) 0.2214(5) 0.1555(2) 0.0303(10) Uani 1 1 d . . . . .
H12 H 0.0600 0.1464 0.1382 0.036 Uiso 1 1 d R U . . .
C3 C 0.11891(19) 0.2817(6) 0.3675(2) 0.0367(11) Uani 1 1 d . . . . .
H3 H 0.1295 0.2930 0.4140 0.044 Uiso 1 1 d R U . . .
C21 C 0.0765(2) 0.6932(6) 0.0762(3) 0.0420(13) Uani 1 1 d . . . . .
C18 C 0.11975(18) 0.8311(8) 0.1742(3) 0.0511(17) Uani 1 1 d . . . . .
C13 C 0.0926(2) 0.2842(6) 0.0391(2) 0.0367(12) Uani 1 1 d . . . . .
C9 C 0.2008(2) 0.8041(6) 0.3278(3) 0.0444(13) Uani 1 1 d . . . . .
H9A H 0.1757 0.8391 0.2947 0.053 Uiso 1 1 d R U . . .
H9B H 0.2250 0.8764 0.3364 0.053 Uiso 1 1 d R U . . .
H9C H 0.1877 0.7811 0.3700 0.053 Uiso 1 1 d R U . . .
C20 C 0.02849(18) 0.5343(6) 0.1667(3) 0.0360(11) Uani 1 1 d . . . . .
C4 C 0.0868(2) 0.1744(6) 0.3474(3) 0.0457(14) Uani 1 1 d . . . . .
H4 H 0.0746 0.1163 0.3802 0.055 Uiso 1 1 d R U . . .
C11 C 0.2417(2) 0.7037(7) 0.2313(4) 0.065(2) Uani 1 1 d . . . . .
H11A H 0.2612 0.6264 0.2177 0.078 Uiso 1 1 d R U . . .
H11B H 0.2605 0.7898 0.2362 0.078 Uiso 1 1 d R U . . .
H11C H 0.2151 0.7178 0.1969 0.078 Uiso 1 1 d R U . . .
C5 C 0.0725(2) 0.1532(6) 0.2779(3) 0.0413(12) Uani 1 1 d . . . . .
H5 H 0.0518 0.0784 0.2639 0.050 Uiso 1 1 d R U . . .
C16 C 0.0440(2) 0.3406(7) 0.0095(3) 0.0491(14) Uani 1 1 d . . . . .
H16A H 0.0191 0.2922 0.0308 0.059 Uiso 1 1 d R U . . .
H16B H 0.0399 0.3238 -0.0393 0.059 Uiso 1 1 d R U . . .
H16C H 0.0423 0.4416 0.0183 0.059 Uiso 1 1 d R U . . .
C14 C 0.1324(2) 0.3667(9) 0.0095(3) 0.0608(19) Uani 1 1 d . . . . .
H14A H 0.1324 0.4642 0.0251 0.073 Uiso 1 1 d R U . . .
H14B H 0.1275 0.3646 -0.0400 0.073 Uiso 1 1 d R U . . .
H14C H 0.1627 0.3231 0.0248 0.073 Uiso 1 1 d R U . . .
C15 C 0.0973(4) 0.1259(7) 0.0223(3) 0.089(3) Uani 1 1 d . . . . .
H15A H 0.1274 0.0888 0.0428 0.106 Uiso 1 1 d R U . . .
H15B H 0.0952 0.1139 -0.0269 0.106 Uiso 1 1 d R U . . .
H15C H 0.0715 0.0749 0.0401 0.106 Uiso 1 1 d R U . . .
C10 C 0.2618(2) 0.6168(8) 0.3522(5) 0.084(2) Uani 1 1 d . U . . .
H10A H 0.2509 0.6076 0.3971 0.101 Uiso 1 1 d R U . . .
H10B H 0.2882 0.6827 0.3545 0.101 Uiso 1 1 d R U . . .
H10C H 0.2721 0.5249 0.3371 0.101 Uiso 1 1 d R U . . .


_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
As1 C1 1.885(4) . ?
As1 N1 2.341(3) . ?
As1 N2 2.346(4) . ?
As1 Cr1 2.6378(9) . ?
Cr1 C17 1.829(5) . ?
Cr1 C18 1.854(7) . ?
Cr1 C21 1.875(5) . ?
Cr1 C19 1.904(5) . ?
Cr1 C20 1.911(6) . ?
O1 C17 1.155(5) . ?
N2 C12 1.285(6) . ?
N2 C13 1.490(6) . ?
N1 C7 1.276(6) . ?
N1 C8 1.498(6) . ?
O3 C19 1.136(6) . ?
C1 C6 1.391(6) . ?
C1 C2 1.403(6) . ?
O2 C18 1.155(8) . ?
O5 C21 1.141(6) . ?
C2 C3 1.400(6) . ?
C2 C7 1.432(6) . ?
O4 C20 1.133(6) . ?
C8 C9 1.506(7) . ?
C8 C11 1.519(8) . ?
C8 C10 1.522(8) . ?
C6 C5 1.387(7) . ?
C6 C12 1.448(6) . ?
C7 H7 0.9299 . ?
C12 H12 0.9301 . ?
C3 C4 1.375(7) . ?
C3 H3 0.9300 . ?
C13 C14 1.518(8) . ?
C13 C16 1.519(7) . ?
C13 C15 1.522(8) . ?
C9 H9A 0.9601 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9599 . ?
C4 C5 1.388(7) . ?
C4 H4 0.9299 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9601 . ?
C11 H11C 0.9599 . ?
C5 H5 0.9299 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 H14A 0.9601 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9601 . ?
C15 H15A 0.9599 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C10 H10A 0.9602 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
C1 As1 N1 77.21(16) . . ?
C1 As1 N2 76.83(16) . . ?
N1 As1 N2 152.59(13) . . ?
C1 As1 Cr1 101.67(13) . . ?
N1 As1 Cr1 97.02(9) . . ?
N2 As1 Cr1 96.70(9) . . ?
C17 Cr1 C18 87.1(2) . . ?
C17 Cr1 C21 88.0(2) . . ?
C18 Cr1 C21 84.6(3) . . ?
C17 Cr1 C19 92.1(2) . . ?
C18 Cr1 C19 90.6(2) . . ?
C21 Cr1 C19 175.2(2) . . ?
C17 Cr1 C20 90.4(2) . . ?
C18 Cr1 C20 176.9(2) . . ?
C21 Cr1 C20 93.6(2) . . ?
C19 Cr1 C20 91.3(2) . . ?
C17 Cr1 As1 178.74(15) . . ?
C18 Cr1 As1 94.15(18) . . ?
C21 Cr1 As1 92.25(16) . . ?
C19 Cr1 As1 87.77(15) . . ?
C20 Cr1 As1 88.37(15) . . ?
C12 N2 C13 120.2(4) . . ?
C12 N2 As1 108.3(3) . . ?
C13 N2 As1 131.4(3) . . ?
C7 N1 C8 120.4(4) . . ?
C7 N1 As1 108.4(3) . . ?
C8 N1 As1 130.9(3) . . ?
C6 C1 C2 118.8(4) . . ?
C6 C1 As1 121.2(3) . . ?
C2 C1 As1 119.8(3) . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 C7 124.1(4) . . ?
C1 C2 C7 116.4(4) . . ?
O1 C17 Cr1 177.3(4) . . ?
N1 C8 C9 108.9(4) . . ?
N1 C8 C11 107.7(4) . . ?
C9 C8 C11 110.3(5) . . ?
N1 C8 C10 110.7(4) . . ?
C9 C8 C10 108.6(5) . . ?
C11 C8 C10 110.7(5) . . ?
O3 C19 Cr1 177.4(5) . . ?
C5 C6 C1 121.1(4) . . ?
C5 C6 C12 123.3(5) . . ?
C1 C6 C12 115.5(4) . . ?
N1 C7 C2 118.0(4) . . ?
N1 C7 H7 120.9 . . ?
C2 C7 H7 121.1 . . ?
N2 C12 C6 118.0(4) . . ?
N2 C12 H12 121.2 . . ?
C6 C12 H12 120.8 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.6 . . ?
O5 C21 Cr1 172.5(5) . . ?
O2 C18 Cr1 173.1(5) . . ?
N2 C13 C14 106.9(4) . . ?
N2 C13 C16 108.8(4) . . ?
C14 C13 C16 110.3(5) . . ?
N2 C13 C15 111.2(4) . . ?
C14 C13 C15 109.2(6) . . ?
C16 C13 C15 110.4(6) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.3 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C20 Cr1 177.2(4) . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 119.7 . . ?
C8 C11 H11A 111.0 . . ?
C8 C11 H11B 108.9 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 108.4 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C5 C4 119.8(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 120.3 . . ?
C13 C16 H16A 109.7 . . ?
C13 C16 H16B 109.3 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.4 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.2 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 110.6 . . ?
C13 C15 H15B 109.2 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 108.6 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C10 H10A 111.3 . . ?
C8 C10 H10B 109.0 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 108.1 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.244 0.500 180 41 ' '
2 0.250 -0.245 1.000 180 41 ' '
3 0.750 0.245 0.000 180 41 ' '
4 0.750 -0.245 0.500 180 41 ' '
_platon_squeeze_details          ?

_refine_diff_density_max         1.679
_refine_diff_density_min         -2.387
_refine_diff_density_rms         0.107
####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 1515233'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H23 As Fe N2 O4'
_chemical_formula_sum            'C20 H23 As Fe N2 O4'
_chemical_formula_weight         486.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'
_symmetry_space_group_name_Hall  'C -2yc'

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

_cell_length_a                   13.9922(4)
_cell_length_b                   16.2860(2)
_cell_length_c                   9.5112(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.863(5)
_cell_angle_gamma                90
_cell_volume                     2112.99(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    14612
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.4

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    2.295
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.214
1 0 -1 0.205
1 0 1 0.149
-1 0 -1 0.156
0 -1 0 0.048
0 1 0 0.024


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.493
_exptl_absorpt_correction_T_max  0.845
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14579
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4586
_reflns_number_gt                4432
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0108P)²+1.9294P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.007(6)
_refine_ls_number_reflns         4586
_refine_ls_number_parameters     253
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0181
_refine_ls_wR_factor_ref         0.0421
_refine_ls_wR_factor_gt          0.0401
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
As1 As 0.853850(14) 0.778130(11) 0.570217(17) 0.02039(5) Uani 1 1 d . . .
Fe1 Fe 0.75826(2) 0.681645(17) 0.39045(3) 0.02127(7) Uani 1 1 d . . .
N2 N 0.81937(11) 0.72023(10) 0.77077(17) 0.0186(3) Uani 1 1 d . . .
C20 C 0.87564(17) 0.63761(13) 0.3970(3) 0.0291(5) Uani 1 1 d . . .
C7 C 0.79408(14) 0.93804(12) 0.4318(2) 0.0210(4) Uani 1 1 d . . .
H7 H 0.7883 0.9866 0.3791 0.025 Uiso 1 1 d R . .
C2 C 0.73217(13) 0.92103(12) 0.5326(2) 0.0189(4) Uani 1 1 d . . .
C12 C 0.75175(14) 0.76032(12) 0.8118(2) 0.0193(4) Uani 1 1 d . . .
H12 H 0.7300 0.7452 0.8936 0.023 Uiso 1 1 d R . .
C1 C 0.75457(13) 0.84828(11) 0.60942(19) 0.0177(4) Uani 1 1 d . . .
C6 C 0.71087(13) 0.83030(12) 0.72494(19) 0.0172(4) Uani 1 1 d . . .
O4 O 0.95076(12) 0.60687(11) 0.4034(2) 0.0440(4) Uani 1 1 d . . .
N1 N 0.85735(11) 0.88351(10) 0.41860(17) 0.0199(3) Uani 1 1 d . . .
C3 C 0.66123(14) 0.97363(12) 0.5650(2) 0.0235(4) Uani 1 1 d . . .
H3 H 0.6457 1.0222 0.5136 0.028 Uiso 1 1 d R . .
O3 O 0.63200(12) 0.63314(11) 0.58444(18) 0.0365(4) Uani 1 1 d . . .
C8 C 0.92965(15) 0.89681(13) 0.3265(2) 0.0253(4) Uani 1 1 d . . .
C5 C 0.63936(13) 0.88305(12) 0.7556(2) 0.0210(4) Uani 1 1 d . . .
H5 H 0.6096 0.8715 0.8315 0.025 Uiso 1 1 d R . .
C17 C 0.70396(17) 0.60597(15) 0.2661(2) 0.0326(5) Uani 1 1 d . . .
C18 C 0.70163(16) 0.76429(14) 0.2781(2) 0.0302(5) Uani 1 1 d . . .
C13 C 0.87972(15) 0.65707(13) 0.8613(2) 0.0260(4) Uani 1 1 d . . .
C9 C 0.87904(18) 0.87805(17) 0.1706(2) 0.0373(5) Uani 1 1 d . . .
H9A H 0.8324 0.9205 0.1343 0.045 Uiso 1 1 d R . .
H9B H 0.9272 0.8754 0.1130 0.045 Uiso 1 1 d R . .
H9C H 0.8458 0.8263 0.1666 0.045 Uiso 1 1 d R . .
O2 O 0.66039(13) 0.81397(12) 0.2025(2) 0.0464(4) Uani 1 1 d . . .
C4 C 0.61399(14) 0.95304(13) 0.6743(2) 0.0246(4) Uani 1 1 d . . .
H4 H 0.5644 0.9868 0.6922 0.030 Uiso 1 1 d R . .
O1 O 0.67016(14) 0.55584(12) 0.1853(2) 0.0499(5) Uani 1 1 d . . .
C11 C 1.01359(17) 0.8374(2) 0.3759(3) 0.0443(7) Uani 1 1 d . . .
H11A H 0.9892 0.7823 0.3612 0.053 Uiso 1 1 d R . .
H11B H 1.0625 0.8462 0.3208 0.053 Uiso 1 1 d R . .
H11C H 1.0421 0.8458 0.4764 0.053 Uiso 1 1 d R . .
C19 C 0.68372(15) 0.65302(13) 0.5131(2) 0.0253(4) Uani 1 1 d . . .
C10 C 0.9678(2) 0.98431(17) 0.3380(3) 0.0507(7) Uani 1 1 d . . .
H10A H 0.9878 0.9993 0.4379 0.061 Uiso 1 1 d R . .
H10B H 1.0228 0.9882 0.2936 0.061 Uiso 1 1 d R . .
H10C H 0.9170 1.0208 0.2902 0.061 Uiso 1 1 d R . .
C14 C 0.9065(2) 0.59189(15) 0.7631(3) 0.0398(6) Uani 1 1 d . . .
H14A H 0.9402 0.6171 0.6967 0.048 Uiso 1 1 d R . .
H14B H 0.9485 0.5518 0.8199 0.048 Uiso 1 1 d R . .
H14C H 0.8480 0.5656 0.7105 0.048 Uiso 1 1 d R . .
C16 C 0.8284(2) 0.61818(17) 0.9696(3) 0.0476(7) Uani 1 1 d . . .
H16A H 0.7665 0.5957 0.9209 0.057 Uiso 1 1 d R . .
H16B H 0.8688 0.5753 1.0207 0.057 Uiso 1 1 d R . .
H16C H 0.8180 0.6595 1.0367 0.057 Uiso 1 1 d R . .
C15 C 0.97341(18) 0.70235(17) 0.9370(3) 0.0454(6) Uani 1 1 d . . .
H15A H 0.9575 0.7451 0.9973 0.055 Uiso 1 1 d R . .
H15B H 1.0178 0.6642 0.9947 0.055 Uiso 1 1 d R . .
H15C H 1.0037 0.7259 0.8652 0.055 Uiso 1 1 d R . .


_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
As1 C1 1.8986(18) . ?
As1 N1 2.2491(16) . ?
As1 N2 2.2737(16) . ?
As1 Fe1 2.4827(3) . ?
Fe1 C17 1.759(2) . ?
Fe1 C20 1.780(2) . ?
Fe1 C18 1.790(2) . ?
Fe1 C19 1.791(2) . ?
N2 C12 1.280(2) . ?
N2 C13 1.479(2) . ?
C20 O4 1.154(3) . ?
C7 N1 1.280(3) . ?
C7 C2 1.455(3) . ?
C7 H7 0.9300 . ?
C2 C1 1.390(3) . ?
C2 C3 1.397(3) . ?
C12 C6 1.448(3) . ?
C12 H12 0.9299 . ?
C1 C6 1.402(3) . ?
C6 C5 1.398(3) . ?
N1 C8 1.494(3) . ?
C3 C4 1.391(3) . ?
C3 H3 0.9300 . ?
O3 C19 1.143(2) . ?
C8 C11 1.514(3) . ?
C8 C10 1.517(3) . ?
C8 C9 1.525(3) . ?
C5 C4 1.379(3) . ?
C5 H5 0.9299 . ?
C17 O1 1.148(3) . ?
C18 O2 1.149(3) . ?
C13 C14 1.515(3) . ?
C13 C16 1.519(3) . ?
C13 C15 1.536(3) . ?
C9 H9A 0.9601 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C4 H4 0.9299 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9601 . ?
C10 H10C 0.9600 . ?
C14 H14A 0.9601 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9599 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C1 As1 N1 77.76(7) . . ?
C1 As1 N2 77.51(7) . . ?
N1 As1 N2 153.29(6) . . ?
C1 As1 Fe1 102.15(5) . . ?
N1 As1 Fe1 97.28(4) . . ?
N2 As1 Fe1 97.64(4) . . ?
C17 Fe1 C20 89.92(11) . . ?
C17 Fe1 C18 93.32(11) . . ?
C20 Fe1 C18 127.32(10) . . ?
C17 Fe1 C19 91.64(10) . . ?
C20 Fe1 C19 122.58(10) . . ?
C18 Fe1 C19 109.87(10) . . ?
C17 Fe1 As1 172.87(8) . . ?
C20 Fe1 As1 83.07(7) . . ?
C18 Fe1 As1 91.96(7) . . ?
C19 Fe1 As1 91.07(6) . . ?
C12 N2 C13 122.84(16) . . ?
C12 N2 As1 110.70(13) . . ?
C13 N2 As1 125.19(12) . . ?
O4 C20 Fe1 177.8(2) . . ?
N1 C7 C2 117.32(17) . . ?
N1 C7 H7 121.1 . . ?
C2 C7 H7 121.6 . . ?
C1 C2 C3 119.67(18) . . ?
C1 C2 C7 114.26(16) . . ?
C3 C2 C7 125.82(18) . . ?
N2 C12 C6 116.89(17) . . ?
N2 C12 H12 121.5 . . ?
C6 C12 H12 121.6 . . ?
C2 C1 C6 120.20(17) . . ?
C2 C1 As1 119.92(14) . . ?
C6 C1 As1 119.60(14) . . ?
C5 C6 C1 119.48(18) . . ?
C5 C6 C12 125.09(17) . . ?
C1 C6 C12 115.19(16) . . ?
C7 N1 C8 122.03(17) . . ?
C7 N1 As1 110.62(13) . . ?
C8 N1 As1 126.93(12) . . ?
C4 C3 C2 119.74(19) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.1 . . ?
N1 C8 C11 107.75(17) . . ?
N1 C8 C10 111.52(18) . . ?
C11 C8 C10 110.0(2) . . ?
N1 C8 C9 108.21(17) . . ?
C11 C8 C9 109.5(2) . . ?
C10 C8 C9 109.8(2) . . ?
C4 C5 C6 119.89(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 120.2 . . ?
O1 C17 Fe1 178.7(2) . . ?
O2 C18 Fe1 175.6(2) . . ?
N2 C13 C14 108.44(16) . . ?
N2 C13 C16 112.95(17) . . ?
C14 C13 C16 110.2(2) . . ?
N2 C13 C15 104.82(17) . . ?
C14 C13 C15 108.8(2) . . ?
C16 C13 C15 111.4(2) . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.4 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C4 C3 120.82(18) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.5 . . ?
C8 C11 H11A 109.1 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.9 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C19 Fe1 175.87(19) . . ?
C8 C10 H10A 109.3 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.6 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C16 H16A 110.1 . . ?
C13 C16 H16B 109.4 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 108.9 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C15 H15A 110.0 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.0 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.045
