# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_pyrbicla
_database_code_depnum_ccdc_archive 'CCDC 1815566'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2018-02-21 downloaded from the CCDC.
;
_audit_creation_date             2017-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 Cl8, 2(H2 O), 2(C3 H5 N2)'
_chemical_formula_sum            'C6 H14 Bi2 Cl8 N4 O2'
_chemical_formula_weight         875.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H14N4O2CL8BI2
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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.310(3)
_cell_length_b                   11.315(4)
_cell_length_c                   13.857(5)
_cell_angle_alpha                71.67(3)
_cell_angle_beta                 89.38(3)
_cell_angle_gamma                77.11(3)
_cell_volume                     1058.4(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7456
_cell_measurement_temperature    240.01(10)
_cell_measurement_theta_max      28.8663
_cell_measurement_theta_min      2.8464
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    17.620
_exptl_absorpt_correction_T_max  0.249
_exptl_absorpt_correction_T_min  0.083
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    2.748
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.1959
_exptl_crystal_size_mid          0.1456
_exptl_crystal_size_min          0.0917
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.926
_diffrn_reflns_theta_min         2.854
_diffrn_ambient_temperature      240.01(10)
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -15.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       15.6585   77.0000  150.0000 112

#__ type_ start__ end____ width___ exp.time_
  2 omega   -6.00   94.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       15.6585   77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega  -56.00   45.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.6741   77.0000  -90.0000 101

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00  100.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       15.6585   57.0000  -60.0000 121

#__ type_ start__ end____ width___ exp.time_
  5 omega  -22.00  100.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       15.6585   37.0000   60.0000 122

#__ type_ start__ end____ width___ exp.time_
  6 omega  -25.00   37.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       15.6585  -99.0000   60.0000 62
;
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0255483000
_diffrn_orient_matrix_UB_12      -0.0620704000
_diffrn_orient_matrix_UB_13      0.0362826000
_diffrn_orient_matrix_UB_21      -0.0367244000
_diffrn_orient_matrix_UB_22      0.0251460000
_diffrn_orient_matrix_UB_23      0.0389015000
_diffrn_orient_matrix_UB_31      -0.0891219000
_diffrn_orient_matrix_UB_32      -0.0106565000
_diffrn_orient_matrix_UB_33      -0.0095053000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4123
_reflns_number_total             4964
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.857
_refine_diff_density_min         -1.119
_refine_diff_density_rms         0.175
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4964
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0196P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0502
_refine_ls_wR_factor_ref         0.0541
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1-H1A = O1-H1B
 0.85 with sigma of 0.01
 O2-H2A = O2-H2B
 0.85 with sigma of 0.01
 H1B-H1A
 1.387 with sigma of 0.02
 H2B-H2A
 1.387 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C4(H4), C5(H5), N6(H6), N7(H7), C8(H8), C9(H9),
 C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.21026(3) 0.14377(2) 0.21487(2) 0.02687(6) Uani 1 1 d . . . . .
Bi2 Bi 0.70363(3) 0.14626(2) 0.45629(2) 0.02451(6) Uani 1 1 d . . . . .
Cl1 Cl 0.1371(2) 0.36132(13) 0.08239(10) 0.0429(4) Uani 1 1 d . . . . .
Cl2 Cl -0.0116(2) 0.07820(16) 0.11353(12) 0.0507(4) Uani 1 1 d . . . . .
Cl3 Cl 0.4845(2) 0.07745(16) 0.11670(12) 0.0514(4) Uani 1 1 d . . . . .
Cl4 Cl 0.4165(2) 0.27914(13) 0.30893(11) 0.0390(3) Uani 1 1 d . . . . .
Cl5 Cl 0.9102(2) 0.27939(13) 0.31316(11) 0.0380(3) Uani 1 1 d . . . . .
Cl6 Cl 0.97658(19) 0.06623(13) 0.60303(10) 0.0365(3) Uani 1 1 d . . . . .
Cl7 Cl 0.4754(2) 0.06700(13) 0.60277(10) 0.0362(3) Uani 1 1 d . . . . .
Cl8 Cl 0.6303(2) 0.35021(13) 0.49975(10) 0.0391(3) Uani 1 1 d . . . . .
O1 O 0.6454(6) 0.3677(4) 0.0947(3) 0.0508(11) Uani 1 1 d D . . . .
H1A H 0.596(7) 0.308(4) 0.132(4) 0.076 Uiso 1 1 d DR . . . .
H1B H 0.7637(19) 0.345(6) 0.108(5) 0.076 Uiso 1 1 d DR . . . .
O2 O 1.1347(7) 0.3677(5) 0.4754(4) 0.0572(12) Uani 1 1 d D . . . .
H2A H 1.245(5) 0.379(7) 0.463(5) 0.086 Uiso 1 1 d DR . . . .
H2B H 1.111(8) 0.320(6) 0.443(5) 0.086 Uiso 1 1 d DR . . . .
N1 N 0.4643(9) 0.5788(6) 0.1602(5) 0.0630(17) Uani 1 1 d . . . . .
H1 H 0.510082 0.504163 0.153456 0.076 Uiso 1 1 calc R . . . .
N2 N 0.3927(9) 0.6848(6) 0.0853(4) 0.0597(16) Uani 1 1 d . . . . .
H2 H 0.382256 0.691023 0.021262 0.072 Uiso 1 1 calc R . . . .
C3 C 0.3401(10) 0.7785(7) 0.1223(5) 0.0568(19) Uani 1 1 d . . . . .
H3 H 0.286481 0.864180 0.084452 0.068 Uiso 1 1 calc R . . . .
C4 C 0.3765(9) 0.7305(6) 0.2268(5) 0.0483(16) Uani 1 1 d . . . . .
H4 H 0.351521 0.775974 0.273564 0.058 Uiso 1 1 calc R . . . .
C5 C 0.4553(11) 0.6045(7) 0.2477(5) 0.0592(19) Uani 1 1 d . . . . .
H5 H 0.496520 0.545411 0.312570 0.071 Uiso 1 1 calc R . . . .
N6 N 0.9562(10) 0.5927(6) 0.2956(6) 0.084(2) Uani 1 1 d . . . . .
H6 H 1.002834 0.518274 0.340259 0.100 Uiso 1 1 calc R . . . .
N7 N 0.8869(9) 0.6987(7) 0.3159(4) 0.0623(17) Uani 1 1 d . . . . .
H7 H 0.879605 0.705308 0.376750 0.075 Uiso 1 1 calc R . . . .
C8 C 0.8310(10) 0.7916(6) 0.2329(5) 0.0556(18) Uani 1 1 d . . . . .
H8 H 0.773905 0.876832 0.227250 0.067 Uiso 1 1 calc R . . . .
C9 C 0.8704(12) 0.7429(10) 0.1547(5) 0.077(3) Uani 1 1 d . . . . .
H9 H 0.850023 0.788737 0.084697 0.092 Uiso 1 1 calc R . . . .
C10 C 0.9434(14) 0.6178(10) 0.1965(8) 0.087(3) Uani 1 1 d . . . . .
H10 H 0.979175 0.558349 0.161356 0.105 Uiso 1 1 calc 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 Cl1 2.5113(18) . ?
Bi1 Cl2 2.5285(17) . ?
Bi1 Cl3 2.5188(17) . ?
Bi1 Cl4 2.9406(16) . ?
Bi1 Cl5 2.9611(17) 1_455 ?
Bi2 Cl4 2.7546(19) . ?
Bi2 Cl5 2.7486(17) . ?
Bi2 Cl6 2.6570(18) . ?
Bi2 Cl7 2.6751(16) . ?
Bi2 Cl8 2.5082(16) . ?
O1 H1A 0.855(10) . ?
O1 H1B 0.850(10) . ?
O2 H2A 0.851(10) . ?
O2 H2B 0.851(10) . ?
N1 H1 0.8700 . ?
N1 N2 1.318(7) . ?
N1 C5 1.331(8) . ?
N2 H2 0.8700 . ?
N2 C3 1.300(8) . ?
C3 H3 0.9400 . ?
C3 C4 1.383(8) . ?
C4 H4 0.9400 . ?
C4 C5 1.351(9) . ?
C5 H5 0.9400 . ?
N6 H6 0.8700 . ?
N6 N7 1.308(8) . ?
N6 C10 1.312(10) . ?
N7 H7 0.8700 . ?
N7 C8 1.286(8) . ?
C8 H8 0.9400 . ?
C8 C9 1.364(9) . ?
C9 H9 0.9400 . ?
C9 C10 1.333(12) . ?
C10 H10 0.9400 . ?

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
Cl1 Bi1 Cl2 88.21(6) . . ?
Cl1 Bi1 Cl3 88.94(6) . . ?
Cl1 Bi1 Cl4 79.83(6) . . ?
Cl1 Bi1 Cl5 80.20(5) . 1_455 ?
Cl2 Bi1 Cl4 166.90(5) . . ?
Cl2 Bi1 Cl5 95.15(6) . 1_455 ?
Cl3 Bi1 Cl2 91.81(6) . . ?
Cl3 Bi1 Cl4 93.28(6) . . ?
Cl3 Bi1 Cl5 166.88(5) . 1_455 ?
Cl4 Bi1 Cl5 77.66(5) . 1_455 ?
Cl5 Bi2 Cl4 82.00(6) . . ?
Cl6 Bi2 Cl4 167.85(4) . . ?
Cl6 Bi2 Cl5 93.92(6) . . ?
Cl6 Bi2 Cl7 86.74(6) . . ?
Cl7 Bi2 Cl4 94.71(6) . . ?
Cl7 Bi2 Cl5 167.16(4) . . ?
Cl8 Bi2 Cl4 82.47(6) . . ?
Cl8 Bi2 Cl5 82.19(5) . . ?
Cl8 Bi2 Cl6 85.64(6) . . ?
Cl8 Bi2 Cl7 85.07(5) . . ?
Bi2 Cl4 Bi1 120.94(6) . . ?
Bi2 Cl5 Bi1 120.78(6) . 1_655 ?
H1A O1 H1B 109(3) . . ?
H2A O2 H2B 108(3) . . ?
N2 N1 H1 125.5 . . ?
N2 N1 C5 109.0(5) . . ?
C5 N1 H1 125.5 . . ?
N1 N2 H2 125.4 . . ?
C3 N2 N1 109.1(5) . . ?
C3 N2 H2 125.4 . . ?
N2 C3 H3 125.8 . . ?
N2 C3 C4 108.3(6) . . ?
C4 C3 H3 125.8 . . ?
C3 C4 H4 127.2 . . ?
C5 C4 C3 105.6(6) . . ?
C5 C4 H4 127.2 . . ?
N1 C5 C4 107.9(6) . . ?
N1 C5 H5 126.1 . . ?
C4 C5 H5 126.1 . . ?
N7 N6 H6 125.8 . . ?
N7 N6 C10 108.3(7) . . ?
C10 N6 H6 125.8 . . ?
N6 N7 H7 124.9 . . ?
C8 N7 N6 110.2(6) . . ?
C8 N7 H7 124.9 . . ?
N7 C8 H8 126.6 . . ?
N7 C8 C9 106.9(7) . . ?
C9 C8 H8 126.6 . . ?
C8 C9 H9 126.6 . . ?
C10 C9 C8 106.8(7) . . ?
C10 C9 H9 126.6 . . ?
N6 C10 C9 107.7(7) . . ?
N6 C10 H10 126.2 . . ?
C9 C10 H10 126.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A Cl3 0.855(10) 2.97(5) 3.653(5) 138(6) .
O1 H1A Cl4 0.855(10) 2.74(5) 3.375(5) 133(6) .
O1 H1B Cl1 0.850(10) 2.79(2) 3.582(5) 156(5) 1_655
O1 H1B Cl5 0.850(10) 2.86(6) 3.358(5) 120(5) .
O2 H2A Cl4 0.851(10) 2.87(5) 3.316(4) 115(5) 1_655
O2 H2A Cl8 0.851(10) 2.80(3) 3.598(5) 157(7) 1_655
O2 H2B Cl5 0.851(10) 2.54(4) 3.311(5) 151(6) .
N1 H1 O1 0.87 2.03 2.866(7) 160.8 .
N2 H2 O1 0.87 1.95 2.769(7) 156.4 2_665
N6 H6 O2 0.87 2.15 2.998(9) 163.6 .
N7 H7 O2 0.87 1.97 2.763(7) 151.8 2_766

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -1 0.0291 0.0000 -0.0000 -1.0000 -0.0363 -0.0389 0.0095
0 0 1 0.0627 -0.0000 0.0000 1.0000 0.0363 0.0389 -0.0095
-10 -7 0 0.0938 -10.0000 -7.0000 -0.0000 0.1790 0.1912 0.9658
10 4 2 0.0766 10.2551 3.9114 2.1447 0.0970 -0.1948 -0.9760
0 -15 -8 0.0643 -0.0000 -15.0000 -8.0000 0.6408 -0.6884 0.2359
0 15 2 0.0694 0.0000 15.0000 2.0000 -0.8585 0.4550 -0.1789
0 -11 8 0.0659 -0.0000 -11.0000 8.0000 0.9730 0.0346 0.0412
0 11 17 0.0779 -0.0000 11.0000 17.0000 -0.0660 0.9379 -0.2788

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jasbabs
_database_code_depnum_ccdc_archive 'CCDC 1815568'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2018-02-21 downloaded from the CCDC.
;
_audit_creation_date             2017-12-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl8 Sb2, 2(H2 O), 2(C3 H5 N2)'
_chemical_formula_sum            'C6 H14 Cl8 N4 O2 Sb2'
_chemical_formula_weight         701.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H14Sb2Cl8N4O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.449(3)
_cell_length_b                   13.654(4)
_cell_length_c                   20.679(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2103.2(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    31470
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.5810
_cell_measurement_theta_min      4.9300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.592
_exptl_absorpt_correction_T_max  0.707
_exptl_absorpt_correction_T_min  0.372
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 18 -12 0.0817
9 8 1 0.1937
1 -18 -10 0.0649
0 1 -29 0.0725
-10 0 4 0.1766
1 -1 29 0.0379
0 15 18 0.0759
9 -11 1 0.1643
-9 -6 -14 0.1711
-1 -5 28 0.0451

_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.3734 17.5091 -12.1363 -0.9370 0.3218 -0.1426
9.4847 8.3167 0.5332 -0.0206 0.9965 -0.0917
0.6448 -18.0951 -9.8617 0.7159 -0.3960 -0.5764
0.4493 1.3199 -29.0832 -0.3825 -0.0425 -0.9244
-10.4247 0.4226 3.7681 -0.3534 -0.8603 0.3700
0.7371 -0.6575 29.0911 0.3962 0.1583 0.9059
-0.4303 15.0807 18.1212 -0.4770 0.3768 0.7952
8.5163 -11.2751 1.1624 0.8262 0.4695 -0.3146
-8.6271 -6.2452 -13.7586 -0.1954 -0.9268 -0.3240
-1.3647 -4.7099 28.0379 0.4884 -0.1165 0.8663

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            44050
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         38.551
_diffrn_reflns_theta_min         4.800
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ      0.00 270.00   1.00   10.00   0.00   0.00   0.00    --   270
  2  ω    -60.00  84.00   1.00   30.00    --   40.00 -79.00   0.00  144
  3  ω    -60.00  84.00   1.00   30.00    --   40.00 -79.00 120.00  144
  4  ω    -60.00  84.00   1.00   30.00    --   40.00 -79.00 240.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0363200000
_diffrn_orient_matrix_UB_12      -0.0446412000
_diffrn_orient_matrix_UB_13      0.0116884000
_diffrn_orient_matrix_UB_21      0.0848302000
_diffrn_orient_matrix_UB_22      0.0228295000
_diffrn_orient_matrix_UB_23      0.0038090000
_diffrn_orient_matrix_UB_31      -0.0233616000
_diffrn_orient_matrix_UB_32      0.0135626000
_diffrn_orient_matrix_UB_33      0.0320381000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                10974
_reflns_number_total             11640
_reflns_odcompleteness_completeness 98.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         2.297
_refine_diff_density_min         -1.122
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.306(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         11640
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0226
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0210P)²+0.4599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0480
_refine_ls_wR_factor_ref         0.0493
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.694(14) 0.306(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3. Restrained distances
 O2-H2A = O2-H2B
 0.85 with sigma of 0.01
 O1-H1A = O1-H1B
 0.85 with sigma of 0.01
 H2B-H2A
 1.387 with sigma of 0.02
 H1B-H1A
 1.387 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C4(H4), C5(H5), N6(H6), N7(H7), C8(H8), C9(H9),
 C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 1.17520(2) 0.49762(2) 0.07252(2) 0.01365(3) Uani 1 1 d . . . . .
Sb2 Sb 0.68331(2) 0.74914(2) 0.07619(2) 0.01262(3) Uani 1 1 d . . . . .
Cl1 Cl 1.16116(9) 0.42152(4) 0.17694(2) 0.01926(10) Uani 1 1 d . . . . .
Cl2 Cl 1.39783(9) 0.38029(4) 0.03761(3) 0.02311(12) Uani 1 1 d . . . . .
Cl3 Cl 0.92465(9) 0.39177(5) 0.03931(3) 0.02195(11) Uani 1 1 d . . . . .
Cl4 Cl 0.93460(8) 0.64032(4) 0.14024(3) 0.01739(9) Uani 1 1 d . . . . .
Cl5 Cl 0.43809(8) 0.61487(4) 0.13714(3) 0.01804(9) Uani 1 1 d . . . . .
Cl6 Cl 0.43155(8) 0.86216(4) 0.04132(3) 0.01771(9) Uani 1 1 d . . . . .
Cl7 Cl 0.91051(8) 0.87110(4) 0.04477(3) 0.01825(10) Uani 1 1 d . . . . .
Cl8 Cl 0.65978(9) 0.82936(4) 0.17911(2) 0.01812(9) Uani 1 1 d . . . . .
O1 O 0.6970(3) 0.44553(13) 0.17869(9) 0.0201(3) Uani 1 1 d D . . . .
H1A H 0.789(3) 0.460(3) 0.1563(17) 0.050(13) Uiso 1 1 d D . . . .
H1B H 0.614(4) 0.482(3) 0.164(2) 0.080(17) Uiso 1 1 d D . . . .
O2 O 0.2017(3) 0.80877(13) 0.17757(9) 0.0200(3) Uani 1 1 d D . . . .
H2A H 0.107(3) 0.779(3) 0.167(2) 0.056(13) Uiso 1 1 d D . . . .
H2B H 0.283(4) 0.801(4) 0.1490(18) 0.073(16) Uiso 1 1 d D . . . .
N1 N 0.8014(4) 0.56027(17) 0.28929(11) 0.0272(5) Uani 1 1 d . . . . .
H1 H 0.784008 0.536461 0.250244 0.033 Uiso 1 1 calc R . . . .
N2 N 0.8242(3) 0.50693(15) 0.34306(10) 0.0248(4) Uani 1 1 d . . . . .
H2 H 0.825075 0.442552 0.345089 0.030 Uiso 1 1 calc R . . . .
C3 C 0.8453(4) 0.56783(19) 0.39308(12) 0.0248(5) Uani 1 1 d . . . . .
H3 H 0.863236 0.549016 0.436832 0.030 Uiso 1 1 calc R . . . .
C4 C 0.8365(4) 0.66276(18) 0.37031(12) 0.0238(5) Uani 1 1 d . . . . .
H4 H 0.847114 0.721268 0.394882 0.029 Uiso 1 1 calc R . . . .
C5 C 0.8091(5) 0.65511(19) 0.30433(12) 0.0270(5) Uani 1 1 d . . . . .
H5 H 0.797843 0.708171 0.274887 0.032 Uiso 1 1 calc R . . . .
N6 N 0.3029(4) 0.69611(17) 0.28710(11) 0.0278(5) Uani 1 1 d . . . . .
H6 H 0.283156 0.721424 0.248618 0.033 Uiso 1 1 calc R . . . .
N7 N 0.3343(3) 0.74685(16) 0.34124(10) 0.0256(4) Uani 1 1 d . . . . .
H7 H 0.339043 0.811108 0.344073 0.031 Uiso 1 1 calc R . . . .
C8 C 0.3572(4) 0.68513(19) 0.38986(13) 0.0269(6) Uani 1 1 d . . . . .
H8 H 0.380648 0.702565 0.433524 0.032 Uiso 1 1 calc R . . . .
C9 C 0.3410(4) 0.59081(18) 0.36613(12) 0.0245(5) Uani 1 1 d . . . . .
H9 H 0.351627 0.531459 0.389798 0.029 Uiso 1 1 calc R . . . .
C10 C 0.3064(5) 0.6008(2) 0.30110(12) 0.0272(5) Uani 1 1 d . . . . .
H10 H 0.288053 0.548805 0.271320 0.033 Uiso 1 1 calc 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 Cl1 2.3987(8) . ?
Sb1 Cl2 2.4162(8) . ?
Sb1 Cl3 2.4584(9) . ?
Sb1 Cl5 2.8606(8) 1_655 ?
Sb2 Cl4 2.7323(8) . ?
Sb2 Cl5 2.8785(8) . ?
Sb2 Cl6 2.5335(9) . ?
Sb2 Cl7 2.4616(8) . ?
Sb2 Cl8 2.4001(8) . ?
O1 H1A 0.847(13) . ?
O1 H1B 0.852(13) . ?
O2 H2A 0.846(13) . ?
O2 H2B 0.849(13) . ?
N1 H1 0.8800 . ?
N1 N2 1.340(3) . ?
N1 C5 1.333(4) . ?
N2 H2 0.8800 . ?
N2 C3 1.337(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(4) . ?
C5 H5 0.9500 . ?
N6 H6 0.8800 . ?
N6 N7 1.337(3) . ?
N6 C10 1.333(4) . ?
N7 H7 0.8800 . ?
N7 C8 1.323(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.376(4) . ?
C10 H10 0.9500 . ?

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
Cl1 Sb1 Cl2 90.67(3) . . ?
Cl1 Sb1 Cl3 87.92(2) . . ?
Cl1 Sb1 Cl5 81.48(2) . 1_655 ?
Cl2 Sb1 Cl3 92.74(4) . . ?
Cl2 Sb1 Cl5 92.34(3) . 1_655 ?
Cl3 Sb1 Cl5 168.288(19) . 1_655 ?
Cl4 Sb2 Cl5 82.89(3) . . ?
Cl6 Sb2 Cl4 167.505(18) . . ?
Cl6 Sb2 Cl5 92.46(3) . . ?
Cl7 Sb2 Cl4 91.42(3) . . ?
Cl7 Sb2 Cl5 169.325(19) . . ?
Cl7 Sb2 Cl6 91.24(3) . . ?
Cl8 Sb2 Cl4 82.43(2) . . ?
Cl8 Sb2 Cl5 81.72(2) . . ?
Cl8 Sb2 Cl6 85.43(2) . . ?
Cl8 Sb2 Cl7 88.60(2) . . ?
Sb1 Cl5 Sb2 125.89(3) 1_455 . ?
H1A O1 H1B 105(3) . . ?
H2A O2 H2B 110(3) . . ?
N2 N1 H1 125.4 . . ?
C5 N1 H1 125.4 . . ?
C5 N1 N2 109.2(2) . . ?
N1 N2 H2 125.7 . . ?
C3 N2 N1 108.6(2) . . ?
C3 N2 H2 125.7 . . ?
N2 C3 H3 125.8 . . ?
N2 C3 C4 108.3(2) . . ?
C4 C3 H3 125.8 . . ?
C3 C4 H4 127.1 . . ?
C3 C4 C5 105.8(2) . . ?
C5 C4 H4 127.1 . . ?
N1 C5 C4 108.0(2) . . ?
N1 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
N7 N6 H6 125.7 . . ?
C10 N6 H6 125.7 . . ?
C10 N6 N7 108.7(2) . . ?
N6 N7 H7 125.4 . . ?
C8 N7 N6 109.2(2) . . ?
C8 N7 H7 125.4 . . ?
N7 C8 H8 125.9 . . ?
N7 C8 C9 108.2(2) . . ?
C9 C8 H8 125.9 . . ?
C8 C9 H9 127.2 . . ?
C10 C9 C8 105.7(2) . . ?
C10 C9 H9 127.2 . . ?
N6 C10 C9 108.2(2) . . ?
N6 C10 H10 125.9 . . ?
C9 C10 H10 125.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A Cl1 0.847(13) 2.85(3) 3.473(3) 131(3) .
O1 H1A Cl3 0.847(13) 2.78(3) 3.424(2) 134(4) .
O1 H1A Cl4 0.847(13) 2.72(4) 3.292(2) 126(3) .
O1 H1B Cl5 0.852(13) 2.30(2) 3.131(2) 164(5) .
O2 H2A Cl4 0.846(13) 2.35(2) 3.137(2) 155(4) 1_455
O2 H2B Cl5 0.849(13) 2.81(5) 3.288(2) 118(4) .
O2 H2B Cl6 0.849(13) 2.62(3) 3.377(2) 148(5) .
O2 H2B Cl8 0.849(13) 2.90(4) 3.424(2) 121(4) .
N1 H1 Cl4 0.88 2.91 3.418(3) 118.8 .
N1 H1 O1 0.88 2.04 2.879(3) 159.8 .
N2 H2 O2 0.88 1.90 2.746(3) 161.7 3_645
N6 H6 Cl5 0.88 2.96 3.444(3) 116.5 .
N6 H6 O2 0.88 1.99 2.840(3) 162.8 .
N7 H7 O1 0.88 1.91 2.754(3) 159.1 3_655

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.155
_oxdiff_exptl_absorpt_empirical_full_min 0.915
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.694(14)
2 0.306(14)

####################################################################### 
# 
# 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_pyrbicl100a
_database_code_depnum_ccdc_archive 'CCDC 1815567'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2018-02-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_pyrbicl100a         
;
PROBLEM: Check Calcd Resid. Dens.  1.72A   From Cl2             4.25 eA-3
RESPONSE: high peaks on the difference Fourier maps results from allotwinning after phase transition
;
_vrf_PLAT971_pyrbicl100a_2       
;
PROBLEM: Check Calcd Resid. Dens.  2.00A   From Cl7             3.77 eA-3
RESPONSE: high peaks on the difference Fourier maps results from allotwinning after phase transition
;
_vrf_PLAT094_pyrbicl100a         
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.01 Report
RESPONSE: high peaks on the difference Fourier maps results from allotwinning after phase transition
;
# Added during the CSD deposition process: Monday 08 January 2018 10:42 PM
# end Validation Reply Form

_audit_creation_date             2017-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 Cl8, 2(H2 O), 2(C3 H5 N2)'
_chemical_formula_sum            'C6 H14 Bi2 Cl8 N4 O2'
_chemical_formula_weight         875.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H14Bi2Cl8N4O2
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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.773(4)
_cell_length_b                   7.213(3)
_cell_length_c                   21.910(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.53(3)
_cell_angle_gamma                90
_cell_volume                     2075.6(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5628
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.7663
_cell_measurement_theta_min      2.8684
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    17.970
_exptl_absorpt_correction_T_max  0.243
_exptl_absorpt_correction_T_min  0.084
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.803
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0642
3 0 -5 0.0497
-3 0 5 0.0497
-3 -5 0 0.0798
0 0 -1 0.0642
3 5 0 0.0798
2 0 -1 0.0620
-3 0 -4 0.0749
3 0 4 0.0749
-1 -10 3 0.0925
1 10 -3 0.0925
-1 0 1 0.0467

_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.099
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -0.0001 0.9998 -0.0311 0.0134 -0.0017
2.9984 -0.0001 -4.9973 0.1716 0.0884 -0.0347
-2.9984 0.0001 4.9973 -0.1716 -0.0884 0.0347
-2.9999 -4.9950 -0.0030 0.0142 -0.0276 0.5164
0.0000 0.0001 -0.9998 0.0311 -0.0134 0.0017
2.9999 4.9950 0.0030 -0.0142 0.0276 -0.5164
1.9989 -0.0003 -0.9984 0.0417 0.0902 -0.0270
-2.9981 0.0008 -4.0022 0.1088 -0.2089 0.0496
2.9981 -0.0008 4.0022 -0.1088 0.2089 -0.0496
-1.3146 -10.1130 2.9665 -0.0386 0.2304 0.9723
1.3146 10.1130 -2.9665 0.0386 -0.2304 -0.9723
-0.9995 0.0001 0.9992 -0.0364 -0.0384 0.0127

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16143
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.766
_diffrn_reflns_theta_min         2.868
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  97.00   1.00   28.00    --   15.66  77.00 150.00  112
  2  ω     -6.00  94.00   1.00   28.00    --   15.66  77.00  30.00  100
  3  ω    -56.00  45.00   1.00   28.00    --  -16.67  77.00 -90.00  101
  4  ω    -21.00  27.00   1.00   28.00    --   15.66  57.00 -60.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0053015000
_diffrn_orient_matrix_UB_12      -0.0060092000
_diffrn_orient_matrix_UB_13      -0.0311526000
_diffrn_orient_matrix_UB_21      0.0517877000
_diffrn_orient_matrix_UB_22      -0.0255910000
_diffrn_orient_matrix_UB_23      0.0133884000
_diffrn_orient_matrix_UB_31      -0.0143527000
_diffrn_orient_matrix_UB_32      -0.0947686000
_diffrn_orient_matrix_UB_33      -0.0016669000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4004
_reflns_number_total             4891
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         3.834
_refine_diff_density_min         -0.957
_refine_diff_density_rms         0.221
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4891
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+0.0921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0646
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1-H1A = O1-H1B
 0.85 with sigma of 0.01
 O2-H2A = O2-H2B
 0.85 with sigma of 0.01
 H1B-H1A
 1.387 with sigma of 0.02
 H2B-H2A
 1.387 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C4(H4), C5(H5), N6(H6), N7(H7), C8(H8), C9(H9),
 C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Bi2 Bi 0.27669(2) 0.59391(3) 0.32215(2) 0.00787(6) Uani 1 1 d . . . . .
Bi1 Bi 0.03296(2) 0.08681(3) 0.31949(2) 0.00880(6) Uani 1 1 d . . . . .
Cl1 Cl 0.00686(11) 0.0787(2) 0.42875(7) 0.0144(3) Uani 1 1 d . . . . .
Cl2 Cl -0.09361(12) -0.1773(2) 0.28897(8) 0.0175(3) Uani 1 1 d . . . . .
Cl3 Cl -0.10631(12) 0.3233(2) 0.28502(8) 0.0186(4) Uani 1 1 d . . . . .
Cl4 Cl 0.18725(11) 0.3560(2) 0.38891(8) 0.0131(3) Uani 1 1 d . . . . .
Cl5 Cl 0.20915(11) 0.8521(2) 0.39074(7) 0.0130(3) Uani 1 1 d . . . . .
Cl6 Cl 0.38824(11) 0.8384(2) 0.28343(7) 0.0126(3) Uani 1 1 d . . . . .
Cl7 Cl 0.38339(11) 0.3327(2) 0.28227(8) 0.0126(3) Uani 1 1 d . . . . .
Cl8 Cl 0.42385(11) 0.5760(2) 0.42499(7) 0.0137(3) Uani 1 1 d . . . . .
O1 O 0.0309(3) 0.6101(6) 0.4348(2) 0.0188(10) Uani 1 1 d D . . . .
H1A H 0.054(5) 0.582(7) 0.404(2) 0.028 Uiso 1 1 d DR . . . .
H1B H 0.034(5) 0.7279(19) 0.439(3) 0.028 Uiso 1 1 d DR . . . .
O2 O 0.4049(3) 1.1145(6) 0.4347(2) 0.0187(10) Uani 1 1 d D . . . .
H2A H 0.403(4) 1.2316(17) 0.430(3) 0.028 Uiso 1 1 d DR . . . .
H2B H 0.351(3) 1.068(7) 0.409(3) 0.028 Uiso 1 1 d DR . . . .
N1 N 0.1962(4) 0.5070(8) 0.5411(3) 0.0215(13) Uani 1 1 d . . . . .
H1 H 0.149952 0.528818 0.504214 0.026 Uiso 1 1 calc R . . . .
N2 N 0.1778(4) 0.4668(8) 0.5963(3) 0.0211(13) Uani 1 1 d . . . . .
H2 H 0.116888 0.460720 0.601451 0.025 Uiso 1 1 calc R . . . .
C3 C 0.2646(5) 0.4375(9) 0.6421(3) 0.0197(15) Uani 1 1 d . . . . .
H3 H 0.272211 0.404968 0.685313 0.024 Uiso 1 1 calc R . . . .
C4 C 0.3415(5) 0.4634(9) 0.6150(3) 0.0186(15) Uani 1 1 d . . . . .
H4 H 0.412523 0.452265 0.635952 0.022 Uiso 1 1 calc R . . . .
C5 C 0.2965(5) 0.5082(9) 0.5520(3) 0.0196(15) Uani 1 1 d . . . . .
H5 H 0.330903 0.535306 0.521419 0.024 Uiso 1 1 calc R . . . .
N6 N 0.3461(4) 1.0071(8) 0.5431(3) 0.0217(13) Uani 1 1 d . . . . .
H6 H 0.356036 1.032004 0.506091 0.026 Uiso 1 1 calc R . . . .
N7 N 0.4179(4) 0.9637(8) 0.5973(3) 0.0196(13) Uani 1 1 d . . . . .
H7 H 0.483313 0.954671 0.601466 0.024 Uiso 1 1 calc R . . . .
C8 C 0.3768(5) 0.9362(9) 0.6443(3) 0.0169(14) Uani 1 1 d . . . . .
H8 H 0.412047 0.905535 0.687491 0.020 Uiso 1 1 calc R . . . .
C9 C 0.2723(5) 0.9608(9) 0.6181(3) 0.0175(15) Uani 1 1 d . . . . .
H9 H 0.221861 0.949057 0.639336 0.021 Uiso 1 1 calc R . . . .
C10 C 0.2572(5) 1.0059(10) 0.5549(3) 0.0220(16) Uani 1 1 d . . . . .
H10 H 0.193225 1.031942 0.524490 0.026 Uiso 1 1 calc 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
Bi2 Cl4 2.7728(16) . ?
Bi2 Cl5 2.7264(16) . ?
Bi2 Cl6 2.6413(15) . ?
Bi2 Cl7 2.6920(16) . ?
Bi2 Cl8 2.5398(19) . ?
Bi1 Cl1 2.5261(16) . ?
Bi1 Cl2 2.5323(16) . ?
Bi1 Cl3 2.5076(16) . ?
Bi1 Cl4 2.9413(17) . ?
Bi1 Cl5 2.9850(17) 1_545 ?
O1 H1A 0.854(10) . ?
O1 H1B 0.854(10) . ?
O2 H2A 0.850(10) . ?
O2 H2B 0.852(10) . ?
N1 H1 0.8800 . ?
N1 N2 1.339(8) . ?
N1 C5 1.330(8) . ?
N2 H2 0.8800 . ?
N2 C3 1.326(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(9) . ?
C5 H5 0.9500 . ?
N6 H6 0.8800 . ?
N6 N7 1.334(8) . ?
N6 C10 1.325(8) . ?
N7 H7 0.8800 . ?
N7 C8 1.331(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(9) . ?
C10 H10 0.9500 . ?

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
Cl5 Bi2 Cl4 81.51(5) . . ?
Cl6 Bi2 Cl4 167.59(5) . . ?
Cl6 Bi2 Cl5 92.81(5) . . ?
Cl6 Bi2 Cl7 86.33(5) . . ?
Cl7 Bi2 Cl4 96.36(5) . . ?
Cl7 Bi2 Cl5 165.29(5) . . ?
Cl8 Bi2 Cl4 82.14(5) . . ?
Cl8 Bi2 Cl5 81.92(5) . . ?
Cl8 Bi2 Cl6 86.16(5) . . ?
Cl8 Bi2 Cl7 83.37(5) . . ?
Cl1 Bi1 Cl2 87.12(5) . . ?
Cl1 Bi1 Cl4 79.17(5) . . ?
Cl1 Bi1 Cl5 79.44(5) . 1_545 ?
Cl2 Bi1 Cl4 164.96(5) . . ?
Cl2 Bi1 Cl5 95.62(6) . 1_545 ?
Cl3 Bi1 Cl1 89.24(5) . . ?
Cl3 Bi1 Cl2 91.66(6) . . ?
Cl3 Bi1 Cl4 94.28(6) . . ?
Cl3 Bi1 Cl5 166.18(5) . 1_545 ?
Cl4 Bi1 Cl5 75.94(5) . 1_545 ?
Bi2 Cl4 Bi1 120.16(6) . . ?
Bi2 Cl5 Bi1 117.24(6) . 1_565 ?
H1A O1 H1B 107(2) . . ?
H2A O2 H2B 109(3) . . ?
N2 N1 H1 126.0 . . ?
C5 N1 H1 126.0 . . ?
C5 N1 N2 108.0(6) . . ?
N1 N2 H2 124.9 . . ?
C3 N2 N1 110.1(5) . . ?
C3 N2 H2 124.9 . . ?
N2 C3 H3 126.6 . . ?
N2 C3 C4 106.8(6) . . ?
C4 C3 H3 126.6 . . ?
C3 C4 H4 126.5 . . ?
C5 C4 C3 107.1(6) . . ?
C5 C4 H4 126.5 . . ?
N1 C5 C4 108.0(6) . . ?
N1 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
N7 N6 H6 126.1 . . ?
C10 N6 H6 126.1 . . ?
C10 N6 N7 107.8(6) . . ?
N6 N7 H7 124.7 . . ?
C8 N7 N6 110.5(5) . . ?
C8 N7 H7 124.7 . . ?
N7 C8 H8 126.6 . . ?
N7 C8 C9 106.8(6) . . ?
C9 C8 H8 126.6 . . ?
C8 C9 H9 127.2 . . ?
C10 C9 C8 105.7(6) . . ?
C10 C9 H9 127.2 . . ?
N6 C10 C9 109.2(6) . . ?
N6 C10 H10 125.4 . . ?
C9 C10 H10 125.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A Cl4 0.854(10) 2.55(5) 3.212(5) 135(6) .
O1 H1A Cl5 0.854(10) 2.97(6) 3.382(4) 112(4) .
O1 H1B Cl1 0.854(10) 2.56(2) 3.395(5) 167(7) 1_565
O2 H2A Cl8 0.850(10) 2.507(12) 3.351(5) 172(5) 1_565
O2 H2B Cl5 0.852(10) 2.43(3) 3.197(5) 149(6) .
N1 H1 O1 0.88 1.96 2.822(7) 166.2 .
N2 H2 Cl3 0.88 2.98 3.400(6) 111.7 3_566
N2 H2 O1 0.88 2.02 2.802(7) 148.2 3_566
N6 H6 O2 0.88 1.97 2.838(7) 167.6 .

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.127
_oxdiff_exptl_absorpt_empirical_full_min 0.845
