# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_2a4mprmsbbr
_database_code_depnum_ccdc_archive 'CCDC 2023492'
loop_
_audit_author_name
_audit_author_address
'Magdalena Owczarek'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br5 Sb, C5 H9 N3, H2 O'
_chemical_formula_sum            'C5 H11 Br5 N3 O Sb'
_chemical_formula_weight         650.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C5 H11 N3 Sb1 Br5 O1'
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'
Br Br -0.2901 2.4595 '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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.296(4)
_cell_length_b                   8.333(3)
_cell_length_c                   16.662(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.10(2)
_cell_angle_gamma                90
_cell_volume                     1490.8(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4942
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.7120
_cell_measurement_theta_min      4.8860
_shelx_estimated_absorpt_T_max   0.462
_shelx_estimated_absorpt_T_min   0.134
_exptl_absorpt_coefficient_mu    15.234
_exptl_absorpt_correction_T_max  0.444
_exptl_absorpt_correction_T_min  0.151
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.898
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 1 23 0.0632
6 -10 2 0.0882
-6 10 -2 0.0882
7 -2 -23 0.0594
2 -11 -6 0.0909
-2 11 6 0.0909
-15 -2 -1 0.0274
15 2 1 0.0274

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
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
-6.9995 0.9987 23.0001 0.8098 0.4465 0.3628
6.0013 -10.0007 1.9989 0.2501 0.1722 -0.9051
-6.0013 10.0007 -1.9989 -0.2501 -0.1722 0.9051
6.9996 -1.9988 -23.0003 -0.7738 -0.4678 -0.4369
2.0012 -11.0004 -6.0016 0.1707 -0.3357 -0.8954
-2.0012 11.0004 6.0016 -0.1707 0.3357 0.8954
-14.9996 -2.0004 -1.0013 0.4604 -0.8668 0.2773
14.9996 2.0004 1.0013 -0.4604 0.8668 -0.2773

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17564
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.504
_diffrn_reflns_theta_min         4.893
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_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   18.00   0.00  29.00 -10.00    --   270
  2  ω     25.00  75.00   1.00   30.00    --   40.00 -79.00   0.00   50
  3  ω    -40.00  75.00   1.00   30.00    --   40.00 -79.00 120.00  115
  4  ω    -40.00 -14.00   1.00   30.00    --   40.00 -79.00 240.00   26
;
_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      -0.0277819000
_diffrn_orient_matrix_UB_12      -0.0360206000
_diffrn_orient_matrix_UB_13      0.0283201000
_diffrn_orient_matrix_UB_21      0.0526480000
_diffrn_orient_matrix_UB_22      0.0212683000
_diffrn_orient_matrix_UB_23      0.0345110000
_diffrn_orient_matrix_UB_31      -0.0286244000
_diffrn_orient_matrix_UB_32      0.0740931000
_diffrn_orient_matrix_UB_33      0.0038472000
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3605
_reflns_number_total             4942
_reflns_odcompleteness_completeness 99.18
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.327
_refine_diff_density_min         -1.337
_refine_diff_density_rms         0.250
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         4942
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.011
_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)+(0.0161P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0670
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O1W-H1WB = O1W-H1WA
 0.88 with sigma of 0.02
 H1WA-H1WB
 1.44 with sigma of 0.02
3.a Riding coordinates:
 N1(H1)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C5(H5), C6(H6)
3.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_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
Sb Sb -0.18954(2) 0.62339(3) 0.23277(2) 0.01075(6) Uani 1 1 d . . . . .
Br2 Br -0.01606(4) 0.38018(4) 0.23497(3) 0.01776(10) Uani 1 1 d . . . . .
Br4 Br -0.35850(4) 0.86153(5) 0.23101(3) 0.01831(10) Uani 1 1 d . . . . .
Br3 Br -0.24812(4) 0.64191(4) 0.06170(3) 0.01736(10) Uani 1 1 d . . . . .
Br5 Br -0.11877(4) 0.61214(5) 0.41129(2) 0.01769(10) Uani 1 1 d . . . . .
Br1 Br -0.35905(4) 0.40891(5) 0.22141(3) 0.01918(10) Uani 1 1 d . . . . .
N3 N 0.1772(3) 0.7243(4) 0.4883(2) 0.0164(8) Uani 1 1 d . . . . .
H3 H 0.097384 0.701726 0.467033 0.020 Uiso 1 1 calc R . . . .
N1 N 0.3754(3) 0.7115(4) 0.4781(2) 0.0160(7) Uani 1 1 d . . . . .
H1 H 0.425842 0.681545 0.451230 0.019 Uiso 1 1 d R . . . .
N2 N 0.2149(4) 0.5756(4) 0.3814(2) 0.0220(8) Uani 1 1 d . . . . .
H2A H 0.266509 0.539122 0.355491 0.026 Uiso 1 1 calc R . . . .
H2B H 0.135516 0.549522 0.362768 0.026 Uiso 1 1 calc R . . . .
C7 C 0.1193(4) 0.8645(5) 0.5973(3) 0.0208(9) Uani 1 1 d . . . . .
H7A H 0.127123 0.980132 0.608301 0.031 Uiso 1 1 calc GR . . . .
H7B H 0.130608 0.806930 0.650467 0.031 Uiso 1 1 calc GR . . . .
H7C H 0.036520 0.840892 0.558121 0.031 Uiso 1 1 calc GR . . . .
C5 C 0.3406(4) 0.8487(5) 0.5921(3) 0.0183(9) Uani 1 1 d . . . . .
H5 H 0.371878 0.907990 0.642993 0.022 Uiso 1 1 calc R . . . .
C6 C 0.4176(4) 0.7976(4) 0.5492(3) 0.0180(9) Uani 1 1 d . . . . .
H6 H 0.503708 0.823401 0.570058 0.022 Uiso 1 1 calc R . . . .
C2 C 0.2563(4) 0.6689(4) 0.4478(3) 0.0164(9) Uani 1 1 d . . . . .
C4 C 0.2153(4) 0.8124(4) 0.5597(3) 0.0166(9) Uani 1 1 d . . . . .
O1W O 0.5609(3) 0.6051(3) 0.4176(2) 0.0229(7) Uani 1 1 d D . . . .
H1WA H 0.631(3) 0.662(5) 0.437(3) 0.034 Uiso 1 1 d DR . . . .
H1WB H 0.560(4) 0.573(5) 0.3668(16) 0.034 Uiso 1 1 d DR . . . .


_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
Sb Br2 3.0799(9) 2 ?
Sb Br2 2.8115(9) . ?
Sb Br4 2.7471(8) . ?
Sb Br3 2.7229(8) . ?
Sb Br5 2.8317(9) . ?
Sb Br1 2.5829(8) . ?
N3 C2 1.358(5) . ?
N3 C4 1.350(5) . ?
N1 C6 1.339(5) . ?
N1 C2 1.330(5) . ?
N2 C2 1.314(5) . ?
C7 C4 1.475(6) . ?
C5 C6 1.355(6) . ?
C5 C4 1.383(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br2 Sb Br2 90.79(3) . 2 ?
Br2 Sb Br5 89.67(2) . . ?
Br4 Sb Br2 89.07(3) . 2 ?
Br4 Sb Br2 179.820(19) . . ?
Br4 Sb Br5 90.20(2) . . ?
Br3 Sb Br2 89.78(2) . . ?
Br3 Sb Br2 93.91(2) . 2 ?
Br3 Sb Br4 90.34(2) . . ?
Br3 Sb Br5 177.421(16) . . ?
Br5 Sb Br2 83.58(2) . 2 ?
Br1 Sb Br2 174.377(16) . 2 ?
Br1 Sb Br2 90.00(3) . . ?
Br1 Sb Br4 90.13(3) . . ?
Br1 Sb Br3 91.66(2) . . ?
Br1 Sb Br5 90.86(2) . . ?
C4 N3 C2 123.0(4) . . ?
C2 N1 C6 121.3(4) . . ?
C6 C5 C4 118.2(4) . . ?
N1 C6 C5 121.6(4) . . ?
N1 C2 N3 117.7(4) . . ?
N2 C2 N3 120.2(4) . . ?
N2 C2 N1 122.1(4) . . ?
N3 C4 C7 117.3(4) . . ?
N3 C4 C5 118.0(4) . . ?
C5 C4 C7 124.6(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
_geom_hbond_publ_flag
N3 H3 Br5 0.88 2.44 3.321(4) 174.5 . yes
N1 H1 O1W 0.86 1.89 2.739(5) 166.7 . yes
N2 H2A Br4 0.88 2.51 3.348(4) 160.4 2_545 yes
N2 H2B Br2 0.88 2.68 3.384(4) 137.6 . yes
O1W H1WA Br3 0.900(18) 2.66(3) 3.412(3) 142(4) 4_676 yes

_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 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.802
####################################################################### 
# 
# 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_2shprmbibr
_database_code_depnum_ccdc_archive 'CCDC 2023491'
loop_
_audit_author_name
_audit_author_address
'Magdalena Owczarek'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Br5, 2(C4 H5 N2 S)'
_chemical_formula_sum            'C8 H10 Bi Br5 N4 S2'
_chemical_formula_weight         834.85
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H10 N4 S2 Bi Br5'
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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 '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                   5.752(4)
_cell_length_b                   15.263(5)
_cell_length_c                   10.633(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.77(2)
_cell_angle_gamma                90
_cell_volume                     902.7(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2826
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.0420
_cell_measurement_theta_min      5.2930
_shelx_estimated_absorpt_T_max   0.187
_shelx_estimated_absorpt_T_min   0.171
_exptl_absorpt_coefficient_mu    21.058
_exptl_absorpt_correction_T_max  0.223
_exptl_absorpt_correction_T_min  0.167
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.072
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -21 -1 0.0686
0 21 1 0.0686
5 12 -11 0.0604
-5 -12 11 0.0604
4 -16 -9 0.0715
-4 16 9 0.0715
1 -8 13 0.0427
7 3 3 0.0600
-7 -3 -3 0.0600
7 -12 0 0.0578
-7 12 0 0.0578
-2 -14 -10 0.0610
-6 7 12 0.0595
6 -7 -12 0.0595
0 8 13 0.0416

_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_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
-0.0000 -21.0000 -1.0000 0.0402 0.1522 0.9652
0.0000 21.0000 1.0000 -0.0402 -0.1522 -0.9652
5.0000 12.0000 -11.0000 -0.4931 -0.8159 -0.3720
-5.0000 -12.0000 11.0000 0.4931 0.8159 0.3720
4.0000 -16.0000 -9.0000 -0.2775 -0.4521 0.8689
-4.0000 16.0000 9.0000 0.2775 0.4521 -0.8689
1.0000 -8.0000 13.0000 0.9677 0.1435 0.2464
7.0000 3.0000 3.0000 0.6066 -0.7614 -0.0774
-7.0000 -3.0000 -3.0000 -0.6066 0.7614 0.0774
7.0000 -12.0000 -0.0000 0.4830 -0.6863 0.6350
-7.0000 12.0000 0.0000 -0.4830 0.6863 -0.6350
-2.0000 -14.0000 -10.0000 -0.7160 0.1873 0.7115
-6.0000 7.0000 12.0000 0.4028 0.7912 -0.5150
6.0000 -7.0000 -12.0000 -0.4028 -0.7912 0.5150
-0.0000 8.0000 13.0000 0.8260 0.1280 -0.4941

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5070
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.692
_diffrn_reflns_theta_min         4.781
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ      0.00 245.00   1.00   30.00   0.00  29.00 -25.00    --   245
  2  ω     25.00  50.00   1.00   55.00    --   40.00 -79.00   0.00   25
;
_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      0.0602712000
_diffrn_orient_matrix_UB_12      -0.0050906000
_diffrn_orient_matrix_UB_13      0.0666687000
_diffrn_orient_matrix_UB_21      -0.1116728000
_diffrn_orient_matrix_UB_22      -0.0079513000
_diffrn_orient_matrix_UB_23      0.0147375000
_diffrn_orient_matrix_UB_31      0.0127361000
_diffrn_orient_matrix_UB_32      -0.0454858000
_diffrn_orient_matrix_UB_33      -0.0100169000
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1902
_reflns_number_total             2247
_reflns_odcompleteness_completeness 97.10
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.921
_refine_diff_density_min         -1.563
_refine_diff_density_rms         0.213
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         2247
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0266
_refine_ls_restrained_S_all      1.029
_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)+(0.0187P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0536
_refine_ls_wR_factor_ref         0.0566
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N1-H1 = N3-H3
 0.88 with sigma of 0.02
3.a Riding coordinates:
 N1(H1), N3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_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
Bi Bi 1.500000 0.500000 0.500000 0.01077(7) Uani 1 2 d S T P . .
Br2 Br 1.34712(9) 0.56022(3) 0.24334(5) 0.02014(12) Uani 1 1 d . . . . .
Br3 Br 1.45361(9) 0.32515(3) 0.41086(5) 0.01549(11) Uani 1 1 d . . . . .
S S 0.2129(2) 0.39972(8) -0.03903(14) 0.0178(3) Uani 1 1 d . . . . .
Br1 Br 1.000000 0.500000 0.500000 0.0289(2) Uani 1 2 d S T P . .
N1 N 0.6685(7) 0.3970(2) 0.1056(4) 0.0148(9) Uani 1 1 d D . . . .
H1 H 0.655499 0.453459 0.088153 0.018 Uiso 1 1 d DR . . . .
C6 C 0.8638(9) 0.3609(3) 0.1818(5) 0.0168(10) Uani 1 1 d . . . . .
H6 H 1.002514 0.395726 0.215530 0.020 Uiso 1 1 calc R . . . .
N3 N 0.4689(7) 0.2663(2) 0.0845(4) 0.0159(9) Uani 1 1 d D . . . .
H3 H 0.339145 0.236750 0.049308 0.019 Uiso 1 1 d DR . . . .
C4 C 0.6608(9) 0.2272(3) 0.1588(5) 0.0167(11) Uani 1 1 d . . . . .
H4 H 0.655756 0.166169 0.175345 0.020 Uiso 1 1 calc R . . . .
C2 C 0.4568(8) 0.3544(3) 0.0532(5) 0.0125(9) Uani 1 1 d . . . . .
C5 C 0.8665(9) 0.2734(3) 0.2123(5) 0.0173(10) Uani 1 1 d . . . . .
H5 H 1.003819 0.246343 0.267465 0.021 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
Bi Br2 2.8004(11) 3_866 ?
Bi Br2 2.8004(11) . ?
Bi Br3 2.8219(9) . ?
Bi Br3 2.8219(9) 3_866 ?
Bi Br1 2.876(2) 1_655 ?
Bi Br1 2.876(2) . ?
S C2 1.645(5) . ?
N1 C6 1.326(7) . ?
N1 C2 1.367(6) . ?
C6 C5 1.373(7) . ?
N3 C4 1.324(7) . ?
N3 C2 1.384(6) . ?
C4 C5 1.370(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br2 Bi Br2 180.0 3_866 . ?
Br2 Bi Br3 89.78(2) . 3_866 ?
Br2 Bi Br3 90.22(2) 3_866 3_866 ?
Br2 Bi Br3 90.22(2) . . ?
Br2 Bi Br3 89.78(2) 3_866 . ?
Br2 Bi Br1 86.24(3) 3_866 1_655 ?
Br2 Bi Br1 86.24(3) . . ?
Br2 Bi Br1 93.76(3) . 1_655 ?
Br2 Bi Br1 93.76(3) 3_866 . ?
Br3 Bi Br3 180.0 . 3_866 ?
Br3 Bi Br1 89.488(12) . . ?
Br3 Bi Br1 90.511(12) 3_866 . ?
Br3 Bi Br1 90.512(12) . 1_655 ?
Br3 Bi Br1 89.489(12) 3_866 1_655 ?
Br1 Bi Br1 180.0 1_655 . ?
Bi Br1 Bi 180.0 1_455 . ?
C6 N1 C2 125.4(4) . . ?
N1 C6 C5 120.4(5) . . ?
C4 N3 C2 124.4(4) . . ?
N3 C4 C5 121.1(4) . . ?
N1 C2 S 125.4(4) . . ?
N1 C2 N3 112.3(4) . . ?
N3 C2 S 122.3(4) . . ?
C4 C5 C6 116.5(5) . . ?

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
_geom_hbond_publ_flag
N1 H1 S 0.88 2.46 3.292(4) 157.0 3_665 yes
N3 H3 Br3 0.87 2.51 3.369(5) 168.1 4_465 yes

_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 1.370
_oxdiff_exptl_absorpt_empirical_full_min 0.812
####################################################################### 
# 
# 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_2shprmsbcl5
_database_code_depnum_ccdc_archive 'CCDC 2023489'
loop_
_audit_author_name
_audit_author_address
'Magdalena Owczarek'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl5 Sb, 2(C4 H5 N2 S)'
_chemical_formula_sum            'C8 H10 Cl5 N4 S2 Sb'
_chemical_formula_weight         525.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H10 N4 S2 Sb Cl5'
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'
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'
S S 0.1246 0.1234 '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      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                   5.540(4)
_cell_length_b                   14.910(5)
_cell_length_c                   10.210(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.08(2)
_cell_angle_gamma                90
_cell_volume                     818.0(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2447
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.4690
_cell_measurement_theta_min      5.4520
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.535
_exptl_absorpt_coefficient_mu    2.751
_exptl_absorpt_correction_T_max  0.832
_exptl_absorpt_correction_T_min  0.683
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.133
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -12 12 0.0410
-2 -13 -10 0.0505
2 13 10 0.0505
7 4 -8 0.0859
-4 7 13 0.0863
0 12 -12 0.0245
-4 -13 -6 0.0610
0 11 12 0.0431
-7 -8 2 0.0809

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
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 -12.0000 12.0000 -0.3481 0.8272 0.5092
-2.0000 -13.0000 -10.0000 0.6611 0.3339 -0.7128
2.0000 13.0000 10.0000 -0.6611 -0.3339 0.7128
7.0000 4.0000 -8.0000 -0.6373 -0.3600 -0.6523
-4.0000 7.0000 13.0000 0.0298 -0.0042 1.0076
0.0000 12.0000 -12.0000 0.3481 -0.8272 -0.5092
-4.0000 -13.0000 -6.0000 0.7789 0.4274 -0.4089
0.0000 11.0000 12.0000 -0.4649 -0.1997 0.8691
-7.0000 -8.0000 2.0000 0.8622 0.3929 0.2412

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5036
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.654
_diffrn_reflns_theta_min         4.929
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ      0.00 221.00   1.00   22.00   0.00  29.00 -20.00    --   221
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1271052000
_diffrn_orient_matrix_UB_12      -0.0050765000
_diffrn_orient_matrix_UB_13      -0.0340866000
_diffrn_orient_matrix_UB_21      0.0018383000
_diffrn_orient_matrix_UB_22      -0.0446475000
_diffrn_orient_matrix_UB_23      0.0242823000
_diffrn_orient_matrix_UB_31      -0.0357426000
_diffrn_orient_matrix_UB_32      0.0156467000
_diffrn_orient_matrix_UB_33      0.0580836000
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2204
_reflns_number_total             2715
_reflns_odcompleteness_completeness 93.85
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.811
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         2715
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0137P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0565
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N1-H1 = N3-H3
 0.88 with sigma of 0.02
3. Others
 Fixed Sof: Cl1(0.5)
4.a Riding coordinates:
 N3(H3), N1(H1)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_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
Sb Sb -0.500000 0.500000 0.500000 0.01472(6) Uani 1 2 d S T P . .
Cl3 Cl -0.46142(11) 0.33350(3) 0.58344(6) 0.01541(12) Uani 1 1 d . . . . .
Cl2 Cl -0.66090(12) 0.44512(4) 0.25448(6) 0.01976(13) Uani 1 1 d . . . . .
Cl1 Cl -0.0941(2) 0.50026(8) 0.48019(13) 0.0190(2) Uani 0.5 1 d . . . . .
C5 C 0.1230(5) 0.26835(14) 0.7818(2) 0.0150(5) Uani 1 1 d . . . . .
H5 H -0.020350 0.240343 0.726835 0.018 Uiso 1 1 calc R . . . .
C4 C 0.3358(5) 0.22019(15) 0.8371(2) 0.0164(5) Uani 1 1 d . . . . .
H4 H 0.341186 0.157681 0.819967 0.020 Uiso 1 1 calc R . . . .
N3 N 0.5349(4) 0.26104(12) 0.91472(19) 0.0147(4) Uani 1 1 d D . . . .
H3 H 0.677758 0.232607 0.949333 0.018 Uiso 1 1 d DR . . . .
N1 N 0.3311(4) 0.39598(12) 0.88749(19) 0.0136(4) Uani 1 1 d D . . . .
H1 H 0.318232 0.451692 0.905909 0.016 Uiso 1 1 d DR . . . .
C6 C 0.1270(5) 0.35830(15) 0.8094(2) 0.0148(5) Uani 1 1 d . . . . .
H6 H -0.015488 0.394052 0.772987 0.018 Uiso 1 1 calc R . . . .
S S 0.79753(11) 0.39826(4) 1.04021(6) 0.01479(12) Uani 1 1 d . . . . .
C2 C 0.5456(4) 0.35135(14) 0.9446(2) 0.0121(4) Uani 1 1 d . . . . .


_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
Sb Cl3 2.6165(9) 3_466 ?
Sb Cl3 2.6164(10) . ?
Sb Cl2 2.5808(13) 3_466 ?
Sb Cl2 2.5808(13) . ?
Sb Cl1 2.306(2) . ?
Sb Cl1 2.306(2) 3_466 ?
Cl1 Cl1 1.023(2) 3_566 ?
C5 C4 1.379(3) . ?
C5 C6 1.370(3) . ?
C4 N3 1.338(3) . ?
N3 C2 1.379(3) . ?
N1 C6 1.338(3) . ?
N1 C2 1.363(3) . ?
S C2 1.651(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
Cl3 Sb Cl3 180.0 . 3_466 ?
Cl2 Sb Cl3 89.83(3) 3_466 3_466 ?
Cl2 Sb Cl3 89.83(3) . . ?
Cl2 Sb Cl3 90.17(3) . 3_466 ?
Cl2 Sb Cl3 90.17(3) 3_466 . ?
Cl2 Sb Cl2 180.0 . 3_466 ?
Cl1 Sb Cl3 88.51(3) . 3_466 ?
Cl1 Sb Cl3 91.49(3) . . ?
Cl1 Sb Cl3 88.51(4) 3_466 . ?
Cl1 Sb Cl3 91.49(3) 3_466 3_466 ?
Cl1 Sb Cl2 91.67(4) . . ?
Cl1 Sb Cl2 88.33(4) . 3_466 ?
Cl1 Sb Cl2 91.67(4) 3_466 3_466 ?
Cl1 Sb Cl2 88.33(4) 3_466 . ?
Cl1 Sb Cl1 180.0 . 3_466 ?
Cl1 Cl1 Sb 152.55(18) 3_566 . ?
C6 C5 C4 117.1(2) . . ?
N3 C4 C5 120.3(2) . . ?
C4 N3 C2 124.1(2) . . ?
C6 N1 C2 124.91(19) . . ?
N1 C6 C5 120.2(2) . . ?
N3 C2 S 121.96(18) . . ?
N1 C2 N3 113.3(2) . . ?
N1 C2 S 124.72(16) . . ?

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
_geom_hbond_publ_flag
N1 H1 S 0.86 2.43 3.274(2) 169.2 3_667 yes

_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 1.062
_oxdiff_exptl_absorpt_empirical_full_min 0.932
####################################################################### 
# 
# 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_2a4mprmsbcl
_database_code_depnum_ccdc_archive 'CCDC 2023495'
loop_
_audit_author_name
_audit_author_address
'Magdalena Owczarek'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl5 Sb, 2(C5 H8 N3), H2 O'
_chemical_formula_sum            'C10 H18 Cl5 N6 O Sb'
_chemical_formula_weight         537.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 N6 Sb Cl5 O H18'
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'
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'
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      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.626(3)
_cell_length_b                   18.512(5)
_cell_length_c                   8.957(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.09(2)
_cell_angle_gamma                90
_cell_volume                     932.7(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13173
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.8200
_cell_measurement_theta_min      3.1560
_shelx_estimated_absorpt_T_max   0.679
_shelx_estimated_absorpt_T_min   0.530
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_T_max  0.779
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.46 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.913
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 -6 -5 0.1107
-1 -26 1 0.1265
1 -25 -3 0.1178
1 -19 9 0.1002
4 23 0 0.1230
-5 18 4 0.0799
7 -9 -4 0.1018
5 1 10 0.0899
0 -7 -12 0.0412
-7 6 5 0.1107

_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
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
6.9995 -5.9997 -4.9990 0.0822 -0.1202 0.9768
-1.0000 -25.9979 1.0007 -0.5802 0.7884 0.2369
0.9998 -24.9982 -2.9987 -0.6285 0.5397 0.5503
0.9999 -18.9978 8.9989 0.1116 1.0148 0.1232
3.9998 22.9982 -0.0008 0.7659 -0.6592 0.0985
-4.9996 17.9987 3.9988 0.2608 -0.2771 -0.9063
6.9995 -8.9994 -3.9991 0.0679 0.0179 0.9914
4.9998 1.0007 9.9980 0.8632 0.4936 0.2362
-0.0001 -7.0002 -11.9976 -0.7619 -0.4469 0.4414
-6.9995 5.9997 4.9990 -0.0822 0.1202 -0.9768

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16596
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.794
_diffrn_reflns_theta_min         3.165
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  60.75   0.75   10.00    --   30.00 -79.00   0.00  153
  2  ω    -54.00  60.75   0.75   10.00    --   30.00 -79.00  90.00  153
  3  ω    -54.00  60.75   0.75   10.00    --   30.00 -79.00 180.00  153
  4  ω    -54.00  60.75   0.75   10.00    --   30.00 -79.00 270.00  153
  5  ω    -54.00  60.75   0.75   20.00    --   48.00 -79.00  45.00  153
  6  ω    -54.00  60.75   0.75   20.00    --   48.00 -79.00 135.00  153
  7  ω    -54.00  60.75   0.75   20.00    --   48.00 -79.00 225.00  153
  8  ω    -54.00  60.75   0.75   20.00    --   48.00 -79.00 315.00  153
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0666595000
_diffrn_orient_matrix_UB_12      0.0217107000
_diffrn_orient_matrix_UB_13      0.0508333000
_diffrn_orient_matrix_UB_21      -0.0029693000
_diffrn_orient_matrix_UB_22      -0.0281456000
_diffrn_orient_matrix_UB_23      0.0536755000
_diffrn_orient_matrix_UB_31      0.1069724000
_diffrn_orient_matrix_UB_32      -0.0143227000
_diffrn_orient_matrix_UB_33      -0.0284339000
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4349
_reflns_number_total             4576
_reflns_odcompleteness_completeness 99.80
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.153
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         4576
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0180
_refine_ls_restrained_S_all      1.124
_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)+(0.0227P)²+0.1494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0438
_refine_ls_wR_factor_ref         0.0443
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O1W-H1WB = O1W-H1WA
 0.88 with sigma of 0.02
 H1WA-H1WB
 1.44 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C5(H5)
3.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_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
Sb Sb 0.41776(2) 0.250000 -0.53265(2) 0.00900(2) Uani 1 2 d S T P . .
Cl1 Cl 0.39483(4) 0.38962(2) -0.54727(3) 0.01460(4) Uani 1 1 d . . . . .
Cl4 Cl 0.41828(6) 0.250000 -0.19595(3) 0.01336(5) Uani 1 2 d S T P . .
Cl2 Cl 0.44890(6) 0.250000 -0.80479(3) 0.01312(5) Uani 1 2 d S T P . .
Cl3 Cl -0.00838(6) 0.250000 -0.53858(4) 0.01768(6) Uani 1 2 d S T P . .
N3 N 0.23751(14) 0.49624(4) 0.12842(9) 0.01149(13) Uani 1 1 d . . . . .
N1 N 0.04091(14) 0.38376(4) 0.12096(9) 0.01263(13) Uani 1 1 d . . . . .
H1 H 0.031312 0.339606 0.084930 0.015 Uiso 1 1 calc R . . . .
N2 N 0.37713(16) 0.40434(5) -0.01960(10) 0.01459(14) Uani 1 1 d . . . . .
H2A H 0.490880 0.433223 -0.049629 0.018 Uiso 1 1 calc R . . . .
H2B H 0.367912 0.359866 -0.053930 0.018 Uiso 1 1 calc R . . . .
C2 C 0.21953(16) 0.42784(5) 0.07745(10) 0.01112(14) Uani 1 1 d . . . . .
C4 C 0.07859(16) 0.51936(5) 0.22640(10) 0.01147(14) Uani 1 1 d . . . . .
C6 C -0.12302(17) 0.40690(5) 0.21929(11) 0.01370(15) Uani 1 1 d . . . . .
H6 H -0.247059 0.375527 0.249057 0.016 Uiso 1 1 calc R . . . .
C7 C 0.10654(19) 0.59445(5) 0.28430(11) 0.01598(16) Uani 1 1 d . . . . .
H7A H 0.200346 0.593605 0.377605 0.024 Uiso 1 1 calc GR . . . .
H7B H -0.050532 0.615081 0.302984 0.024 Uiso 1 1 calc GR . . . .
H7C H 0.188165 0.624011 0.210382 0.024 Uiso 1 1 calc GR . . . .
C5 C -0.10936(17) 0.47521(5) 0.27521(11) 0.01382(15) Uani 1 1 d . . . . .
H5 H -0.221920 0.492501 0.344402 0.017 Uiso 1 1 calc R . . . .
O1W O -0.05989(18) 0.250000 -0.03025(12) 0.01506(18) Uani 1 2 d DS T P . .
H1WA H 0.043(3) 0.250000 -0.101(2) 0.023 Uiso 1 2 d DRS T P . .
H1WB H -0.203(3) 0.250000 -0.066(2) 0.023 Uiso 1 2 d DRS T P . .


_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
Sb Cl1 2.5910(7) . ?
Sb Cl1 2.5910(7) 4_565 ?
Sb Cl4 3.0157(14) . ?
Sb Cl2 2.4472(11) . ?
Sb Cl3 2.3971(13) . ?
N3 C2 1.3491(12) . ?
N3 C4 1.3352(13) . ?
N1 C2 1.3574(13) . ?
N1 C6 1.3568(13) . ?
N2 C2 1.3268(13) . ?
C4 C7 1.4908(14) . ?
C4 C5 1.4124(14) . ?
C6 C5 1.3617(14) . ?

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 Sb Cl1 171.939(12) 4_565 . ?
Cl1 Sb Cl4 92.847(6) 4_565 . ?
Cl1 Sb Cl4 92.847(6) . . ?
Cl2 Sb Cl1 87.368(6) . . ?
Cl2 Sb Cl1 87.367(6) . 4_565 ?
Cl2 Sb Cl4 175.840(11) . . ?
Cl3 Sb Cl1 87.138(6) . . ?
Cl3 Sb Cl1 87.138(6) . 4_565 ?
Cl3 Sb Cl4 90.24(2) . . ?
Cl3 Sb Cl2 93.92(2) . . ?
C4 N3 C2 118.46(8) . . ?
C6 N1 C2 120.84(8) . . ?
N3 C2 N1 121.21(8) . . ?
N2 C2 N3 118.86(8) . . ?
N2 C2 N1 119.91(9) . . ?
N3 C4 C7 117.39(8) . . ?
N3 C4 C5 122.18(9) . . ?
C5 C4 C7 120.43(9) . . ?
N1 C6 C5 119.85(9) . . ?
C6 C5 C4 117.44(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
_geom_hbond_publ_flag
N1 H1 O1W 0.88 2.01 2.8736(12) 165.0 . yes
N2 H2A N3 0.88 2.14 3.0197(15) 178.4 3_665 yes
N2 H2B Cl4 0.88 2.42 3.2750(11) 164.5 . yes
O1W H1WA Cl4 0.870(15) 2.289(15) 3.0971(17) 154.6(19) . yes
O1W H1WB Cl4 0.861(15) 2.408(15) 3.2644(19) 172.8(19) 1_455 yes

_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 1.143
_oxdiff_exptl_absorpt_empirical_full_min 0.909
####################################################################### 
# 
# 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_2a4mprmbibr
_database_code_depnum_ccdc_archive 'CCDC 2023494'
loop_
_audit_author_name
_audit_author_address
'Magdalena Owczarek'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 Br10, 4(C5 H8 N3)'
_chemical_formula_sum            'C20 H32 Bi2 Br10 N12'
_chemical_formula_weight         1657.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H32 Bi2 Br10 N12'
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'
Br Br -0.2901 2.4595 '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'

_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                   9.775(4)
_cell_length_b                   9.808(4)
_cell_length_c                   11.435(5)
_cell_angle_alpha                76.78(2)
_cell_angle_beta                 65.46(2)
_cell_angle_gamma                82.72(2)
_cell_volume                     970.2(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7238
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.6000
_cell_measurement_theta_min      3.0760
_shelx_estimated_absorpt_T_max   0.204
_shelx_estimated_absorpt_T_min   0.120
_exptl_absorpt_coefficient_mu    19.386
_exptl_absorpt_correction_T_max  0.226
_exptl_absorpt_correction_T_min  0.089
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.837
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 14 3 0.0842
3 5 16 0.0746
-13 4 -6 0.0845
12 -2 11 0.0346
-2 2 -14 0.0498
-9 -1 6 0.0751
9 1 -6 0.0751
-3 -14 -3 0.0842
-6 -4 -16 0.0541

_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_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
2.9993 14.0003 2.9995 0.7265 -0.5881 -0.4097
3.0000 5.0006 16.0007 0.4827 0.5776 -0.6967
-13.0012 3.9996 -6.0000 -0.5457 -0.5640 -0.6688
12.0010 -1.9995 11.0003 0.6166 0.7159 0.3165
-2.0004 1.9996 -14.0009 -0.1403 -0.8467 0.4384
-9.0005 -1.0000 6.0008 -0.4400 0.3445 -0.7946
9.0005 1.0000 -6.0008 0.4400 -0.3445 0.7946
-2.9993 -14.0003 -2.9995 -0.7265 0.5881 0.4097
-6.0003 -4.0006 -16.0006 -0.5939 -0.6393 0.4776

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9141
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.850
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  70.75   0.75   20.00    --   30.00 -79.00   0.00  193
  2  ω    -74.00  70.75   0.75   20.00    --   30.00 -79.00  90.00  193
  3  ω    -74.00  70.75   0.75   20.00    --   30.00 -79.00 180.00  193
  4  ω    -74.00  70.75   0.75   20.00    --   30.00 -79.00 270.00  193
  5  ω    -54.00  10.50   0.75   40.00    --   48.00 -79.00  45.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0501615000
_diffrn_orient_matrix_UB_12      0.0393273000
_diffrn_orient_matrix_UB_13      0.0084737000
_diffrn_orient_matrix_UB_21      0.0026435000
_diffrn_orient_matrix_UB_22      -0.0538003000
_diffrn_orient_matrix_UB_23      0.0524150000
_diffrn_orient_matrix_UB_31      0.0620215000
_diffrn_orient_matrix_UB_32      -0.0329357000
_diffrn_orient_matrix_UB_33      -0.0448749000
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3955
_reflns_number_total             4262
_reflns_odcompleteness_completeness 99.47
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.133
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.181
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0207
_refine_ls_restrained_S_all      1.064
_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)+(0.0265P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0515
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3B(H3B), N1A(H1A), C6B(H6B), C6A(H6A), C5A(H5A), C5B(H5B)
2.b X=CH2 refined with riding coordinates:
 N2B(H2BA,H2BB), N2A(H2AA,H2AB)
2.c Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C7B(H7BA,H7BB,H7BC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Bi Bi 0.22493(2) 0.02578(2) 0.32041(2) 0.01192(5) Uani 1 1 d . . . . .
Br5 Br 0.23882(4) 0.32078(4) 0.30121(4) 0.01607(9) Uani 1 1 d . . . . .
Br4 Br 0.52159(4) -0.01460(4) 0.30634(4) 0.01617(9) Uani 1 1 d . . . . .
Br3 Br 0.21724(4) -0.26052(4) 0.33294(4) 0.01725(9) Uani 1 1 d . . . . .
Br1 Br 0.29605(4) 0.07576(4) 0.06320(4) 0.01734(9) Uani 1 1 d . . . . .
Br2 Br -0.10511(4) 0.05960(4) 0.37268(4) 0.01482(8) Uani 1 1 d . . . . .
N3B N 0.6017(3) 0.3203(3) 0.2386(3) 0.0152(7) Uani 1 1 d . . . . .
H3B H 0.605528 0.228096 0.254406 0.018 Uiso 1 1 calc R . . . .
N1B N 0.5600(3) 0.5275(3) 0.3211(3) 0.0153(7) Uani 1 1 d . . . . .
N3A N 0.0476(3) 0.4024(3) 0.8609(3) 0.0139(7) Uani 1 1 d . . . . .
N2B N 0.5374(4) 0.3116(4) 0.4582(3) 0.0192(7) Uani 1 1 d . . . . .
H2BA H 0.515479 0.353739 0.524292 0.023 Uiso 1 1 calc R . . . .
H2BB H 0.540567 0.219518 0.471124 0.023 Uiso 1 1 calc R . . . .
N2A N 0.0296(4) 0.6412(3) 0.8510(3) 0.0186(7) Uani 1 1 d . . . . .
H2AA H -0.001152 0.626138 0.936739 0.022 Uiso 1 1 calc R . . . .
H2AB H 0.038731 0.727489 0.805461 0.022 Uiso 1 1 calc R . . . .
N1A N 0.1113(3) 0.5593(3) 0.6577(3) 0.0152(7) Uani 1 1 d . . . . .
H1A H 0.118283 0.646199 0.613792 0.018 Uiso 1 1 calc R . . . .
C2A C 0.0620(4) 0.5341(4) 0.7904(4) 0.0142(8) Uani 1 1 d . . . . .
C6B C 0.5910(4) 0.5975(4) 0.1985(4) 0.0192(8) Uani 1 1 d . . . . .
H6B H 0.585362 0.697045 0.183622 0.023 Uiso 1 1 calc R . . . .
C4A C 0.0823(4) 0.2961(4) 0.7978(4) 0.0144(8) Uani 1 1 d . . . . .
C7A C 0.0567(4) 0.1517(4) 0.8787(4) 0.0183(8) Uani 1 1 d . . . . .
H7AA H -0.020773 0.108826 0.866903 0.027 Uiso 1 1 calc GR . . . .
H7AB H 0.023458 0.156202 0.971293 0.027 Uiso 1 1 calc GR . . . .
H7AC H 0.150647 0.095181 0.851105 0.027 Uiso 1 1 calc GR . . . .
C6A C 0.1501(4) 0.4518(4) 0.5923(4) 0.0166(8) Uani 1 1 d . . . . .
H6A H 0.186289 0.470249 0.499355 0.020 Uiso 1 1 calc R . . . .
C2B C 0.5653(4) 0.3865(4) 0.3397(4) 0.0134(7) Uani 1 1 d . . . . .
C4B C 0.6327(4) 0.3904(4) 0.1131(4) 0.0166(8) Uani 1 1 d . . . . .
C7B C 0.6632(5) 0.3052(4) 0.0130(4) 0.0203(9) Uani 1 1 d . . . . .
H7BA H 0.744291 0.235682 0.014055 0.030 Uiso 1 1 calc GR . . . .
H7BB H 0.693536 0.366325 -0.073784 0.030 Uiso 1 1 calc GR . . . .
H7BC H 0.572024 0.257153 0.032375 0.030 Uiso 1 1 calc GR . . . .
C5A C 0.1368(4) 0.3179(4) 0.6600(4) 0.0186(8) Uani 1 1 d . . . . .
H5A H 0.163400 0.241105 0.616051 0.022 Uiso 1 1 calc R . . . .
C5B C 0.6310(4) 0.5336(4) 0.0916(4) 0.0173(8) Uani 1 1 d . . . . .
H5B H 0.656406 0.588046 0.005705 0.021 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
Bi Br5 2.8676(12) . ?
Bi Br4 2.8182(12) . ?
Bi Br3 2.7878(12) . ?
Bi Br1 2.6651(13) . ?
Bi Br2 3.1432(15) 2_556 ?
Bi Br2 3.0155(14) . ?
N3B C2B 1.351(5) . ?
N3B C4B 1.366(5) . ?
N1B C6B 1.337(5) . ?
N1B C2B 1.348(5) . ?
N3A C2A 1.346(5) . ?
N3A C4A 1.332(5) . ?
N2B C2B 1.318(5) . ?
N2A C2A 1.323(5) . ?
N1A C2A 1.359(5) . ?
N1A C6A 1.356(5) . ?
C6B C5B 1.390(5) . ?
C4A C7A 1.490(5) . ?
C4A C5A 1.411(5) . ?
C6A C5A 1.355(6) . ?
C4B C7B 1.479(5) . ?
C4B C5B 1.369(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br5 Bi Br2 97.18(3) . 2_556 ?
Br5 Bi Br2 90.53(2) . . ?
Br4 Bi Br5 90.14(2) . . ?
Br4 Bi Br2 172.732(12) . . ?
Br4 Bi Br2 89.10(3) . 2_556 ?
Br3 Bi Br5 178.580(12) . . ?
Br3 Bi Br4 89.19(2) . . ?
Br3 Bi Br2 90.29(2) . . ?
Br3 Bi Br2 84.06(3) . 2_556 ?
Br1 Bi Br5 88.34(3) . . ?
Br1 Bi Br4 96.88(3) . . ?
Br1 Bi Br3 90.50(3) . . ?
Br1 Bi Br2 171.870(12) . 2_556 ?
Br1 Bi Br2 90.37(3) . . ?
Br2 Bi Br2 83.64(3) . 2_556 ?
Bi Br2 Bi 96.36(3) . 2_556 ?
C2B N3B C4B 122.8(3) . . ?
C6B N1B C2B 116.6(3) . . ?
C4A N3A C2A 118.6(3) . . ?
C6A N1A C2A 120.7(3) . . ?
N3A C2A N1A 121.2(3) . . ?
N2A C2A N3A 119.6(4) . . ?
N2A C2A N1A 119.2(3) . . ?
N1B C6B C5B 124.0(4) . . ?
N3A C4A C7A 117.5(3) . . ?
N3A C4A C5A 121.8(4) . . ?
C5A C4A C7A 120.7(4) . . ?
C5A C6A N1A 119.7(4) . . ?
N1B C2B N3B 121.2(4) . . ?
N2B C2B N3B 119.3(4) . . ?
N2B C2B N1B 119.5(3) . . ?
N3B C4B C7B 117.3(4) . . ?
N3B C4B C5B 116.9(4) . . ?
C5B C4B C7B 125.9(4) . . ?
C6A C5A C4A 118.0(4) . . ?
C4B C5B C6B 118.4(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
_geom_hbond_publ_flag
N3B H3B Br4 0.88 2.48 3.315(3) 159.3 . yes
N2B H2BA N1B 0.88 2.16 3.036(5) 172.6 2_666 yes
N2B H2BB Br4 0.88 2.75 3.409(4) 132.5 2_656 yes
N2A H2AA N3A 0.88 2.12 2.997(5) 172.7 2_567 yes
N2A H2AB Br2 0.88 2.50 3.354(4) 164.8 2_566 yes
N1A H1A Br2 0.88 2.91 3.669(4) 145.7 2_566 yes

_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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.799
####################################################################### 
# 
# 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_2aprmbicl_centro
_database_code_depnum_ccdc_archive 'CCDC 2025388'
loop_
_audit_author_name
_audit_author_address
'Magdalena Owczarek'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 Cl10, 4(C4 H6 N3), 2(H2 O)'
_chemical_formula_sum            'C16 H28 Bi2 Cl10 N12 O2'
_chemical_formula_weight         1192.96
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H28 N12 Bi2 Cl10 O2'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   19.226(4)
_cell_length_b                   13.018(4)
_cell_length_c                   14.193(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.74(2)
_cell_angle_gamma                90
_cell_volume                     3490.1(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5315
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      37.0390
_cell_measurement_theta_min      4.8030
_shelx_estimated_absorpt_T_max   0.561
_shelx_estimated_absorpt_T_min   0.259
_exptl_absorpt_coefficient_mu    10.875
_exptl_absorpt_correction_T_max  0.566
_exptl_absorpt_correction_T_min  0.307
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-23 9 -1 0.0416
-15 -7 -12 0.0482
-7 -17 5 0.0411
10 13 -14 0.0520
16 -15 -2 0.0420
-16 15 2 0.0420
-12 -16 -1 0.0313
12 16 1 0.0313
23 -9 1 0.0416
-2 1 20 0.0682
7 17 -5 0.0411

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
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
-23.0048 9.0029 -1.0013 0.4107 0.2393 0.8820
-15.0019 -7.0005 -12.0053 0.9788 -0.0618 0.0524
-7.0023 -17.0039 5.0008 0.4305 0.5752 -0.6711
10.0039 13.0034 -14.0040 -0.0986 -0.8988 0.4814
16.0035 -15.0039 -2.0003 0.0239 -0.1298 -0.9990
-16.0035 15.0039 2.0003 -0.0239 0.1298 0.9990
-12.0027 -16.0032 -1.0015 0.7434 0.4291 -0.4883
12.0027 16.0032 1.0015 -0.7434 -0.4291 0.4883
23.0048 -9.0029 1.0013 -0.4107 -0.2393 -0.8820
-2.0028 0.9993 20.0070 -0.6638 0.7573 -0.0350
7.0023 17.0039 -5.0008 -0.4305 -0.5752 0.6711

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13638
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.146
_diffrn_reflns_theta_min         4.741
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  84.00   1.00   70.00    --   40.00 -79.00   0.00  144
  2  ω    -60.00  69.00   1.00   60.00    --   40.00 -79.00 120.00  129
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0260397000
_diffrn_orient_matrix_UB_12      -0.0247582000
_diffrn_orient_matrix_UB_13      -0.0345507000
_diffrn_orient_matrix_UB_21      -0.0180913000
_diffrn_orient_matrix_UB_22      -0.0155513000
_diffrn_orient_matrix_UB_23      0.0368200000
_diffrn_orient_matrix_UB_31      -0.0200920000
_diffrn_orient_matrix_UB_32      0.0459595000
_diffrn_orient_matrix_UB_33      -0.0060565000
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5004
_reflns_number_total             6456
_reflns_odcompleteness_completeness 99.06
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.658
_refine_diff_density_min         -1.046
_refine_diff_density_rms         0.190
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         6456
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      0.966
_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)+(0.0064P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0414
_refine_ls_wR_factor_ref         0.0463
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1W-H1WB = O1W-H1WA
 0.88 with sigma of 0.02
 H1WA-H1WB
 1.44 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N1B(H1B), C5A(H5A), C6A(H6A), N1A(H1A), C5B(H5B), C6B(H6B), C4A(H4A), C4B(H4B)
3.b X=CH2 refined with riding coordinates:
 N2B(H2BA,H2BB), N2A(H2AA,H2AB)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_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
Bi Bi 0.29347(2) 0.40275(2) 0.48119(2) 0.01534(3) Uani 1 1 d . . . . .
Cl4 Cl 0.36443(4) 0.40616(7) 0.65683(5) 0.02298(17) Uani 1 1 d . . . . .
Cl3 Cl 0.40245(4) 0.46727(7) 0.42557(7) 0.0273(2) Uani 1 1 d . . . . .
Cl1 Cl 0.24486(4) 0.59103(7) 0.50727(5) 0.02117(16) Uani 1 1 d . . . . .
Cl5 Cl 0.16811(4) 0.30003(7) 0.54307(6) 0.02307(18) Uani 1 1 d . . . . .
Cl2 Cl 0.22685(4) 0.40765(8) 0.28940(6) 0.0294(2) Uani 1 1 d . . . . .
N1B N -0.12610(13) 0.2884(2) 0.67386(19) 0.0207(6) Uani 1 1 d . . . . .
H1B H -0.165617 0.307629 0.691550 0.025 Uiso 1 1 calc R . . . .
C5A C 0.03125(17) 0.7966(3) 0.6223(2) 0.0228(7) Uani 1 1 d . . . . .
H5A H 0.015921 0.865302 0.627739 0.027 Uiso 1 1 calc R . . . .
C2B C -0.08003(17) 0.3607(3) 0.6561(2) 0.0184(7) Uani 1 1 d . . . . .
N3B N -0.01849(14) 0.3350(2) 0.62856(19) 0.0199(6) Uani 1 1 d . . . . .
N3A N 0.00506(14) 0.6161(2) 0.62303(19) 0.0199(6) Uani 1 1 d . . . . .
C6A C 0.09701(18) 0.7752(3) 0.6059(2) 0.0237(8) Uani 1 1 d . . . . .
H6A H 0.129621 0.828802 0.600922 0.028 Uiso 1 1 calc R . . . .
N1A N 0.11514(13) 0.6757(2) 0.59688(19) 0.0212(6) Uani 1 1 d . . . . .
H1A H 0.157656 0.661294 0.585976 0.025 Uiso 1 1 calc R . . . .
N2B N -0.09390(14) 0.4592(2) 0.6664(2) 0.0242(7) Uani 1 1 d . . . . .
H2BA H -0.133280 0.477640 0.684921 0.029 Uiso 1 1 calc R . . . .
H2BB H -0.063741 0.506234 0.654727 0.029 Uiso 1 1 calc R . . . .
C5B C -0.05210(17) 0.1578(3) 0.6374(2) 0.0247(8) Uani 1 1 d . . . . .
H5B H -0.041203 0.087422 0.629785 0.030 Uiso 1 1 calc R . . . .
C6B C -0.11318(17) 0.1867(3) 0.6652(2) 0.0233(8) Uani 1 1 d . . . . .
H6B H -0.146121 0.136793 0.678372 0.028 Uiso 1 1 calc R . . . .
C4A C -0.01279(17) 0.7137(3) 0.6307(2) 0.0206(7) Uani 1 1 d . . . . .
H4A H -0.058804 0.727964 0.642673 0.025 Uiso 1 1 calc R . . . .
C4B C -0.00620(17) 0.2356(3) 0.6206(2) 0.0220(7) Uani 1 1 d . . . . .
H4B H 0.036917 0.215983 0.602040 0.026 Uiso 1 1 calc R . . . .
C2A C 0.07003(16) 0.5978(3) 0.6041(2) 0.0189(6) Uani 1 1 d . . . . .
N2A N 0.08942(14) 0.5023(2) 0.5930(2) 0.0261(7) Uani 1 1 d . . . . .
H2AA H 0.060101 0.451571 0.597955 0.031 Uiso 1 1 calc R . . . .
H2AB H 0.131705 0.489246 0.580573 0.031 Uiso 1 1 calc R . . . .
O1W O 0.25074(15) 0.6656(3) 0.28079(18) 0.0400(8) Uani 1 1 d D . . . .
H1WA H 0.248(2) 0.696(3) 0.227(2) 0.060 Uiso 1 1 d DR . . . .
H1WB H 0.255(2) 0.5998(14) 0.277(3) 0.060 Uiso 1 1 d DR . . . .


_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
Bi Cl4 2.6096(11) . ?
Bi Cl3 2.5171(9) . ?
Bi Cl1 2.6733(11) . ?
Bi Cl5 2.7799(11) 7_556 ?
Bi Cl5 3.0261(9) . ?
Bi Cl2 2.7847(11) . ?
N1B C2B 1.349(4) . ?
N1B C6B 1.356(4) . ?
C5A C6A 1.356(4) . ?
C5A C4A 1.390(5) . ?
C2B N3B 1.355(4) . ?
C2B N2B 1.323(4) . ?
N3B C4B 1.324(4) . ?
N3A C4A 1.326(4) . ?
N3A C2A 1.347(4) . ?
C6A N1A 1.353(4) . ?
N1A C2A 1.350(4) . ?
C5B C6B 1.360(5) . ?
C5B C4B 1.393(5) . ?
C2A N2A 1.315(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl4 Bi Cl1 89.21(3) . . ?
Cl4 Bi Cl5 91.76(3) . 7_556 ?
Cl4 Bi Cl5 91.90(3) . . ?
Cl4 Bi Cl2 175.36(3) . . ?
Cl3 Bi Cl4 88.64(3) . . ?
Cl3 Bi Cl1 94.03(3) . . ?
Cl3 Bi Cl5 173.25(3) . . ?
Cl3 Bi Cl5 91.26(3) . 7_556 ?
Cl3 Bi Cl2 86.79(3) . . ?
Cl1 Bi Cl5 92.70(3) . . ?
Cl1 Bi Cl5 174.64(2) . 7_556 ?
Cl1 Bi Cl2 90.31(3) . . ?
Cl5 Bi Cl5 82.00(3) 7_556 . ?
Cl5 Bi Cl2 89.15(3) 7_556 . ?
Cl2 Bi Cl5 92.73(3) . . ?
Bi Cl5 Bi 98.00(3) 7_556 . ?
C2B N1B C6B 121.8(3) . . ?
C6A C5A C4A 117.2(3) . . ?
N1B C2B N3B 121.3(3) . . ?
N2B C2B N1B 120.2(3) . . ?
N2B C2B N3B 118.5(3) . . ?
C4B N3B C2B 116.5(3) . . ?
C4A N3A C2A 116.7(3) . . ?
N1A C6A C5A 118.5(3) . . ?
C2A N1A C6A 122.1(3) . . ?
C6B C5B C4B 117.2(3) . . ?
N1B C6B C5B 118.6(3) . . ?
N3A C4A C5A 124.4(3) . . ?
N3B C4B C5B 124.5(3) . . ?
N3A C2A N1A 121.0(3) . . ?
N2A C2A N3A 119.0(3) . . ?
N2A C2A N1A 120.0(3) . . ?

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
_geom_hbond_publ_flag
N1B H1B O1W 0.88 1.79 2.663(4) 173.2 5_566 yes
N1A H1A Cl1 0.88 2.37 3.199(3) 158.3 . yes
N2B H2BA Cl2 0.88 2.42 3.245(3) 156.9 5_566 yes
N2B H2BB N3A 0.88 2.05 2.934(4) 178.2 . yes
N2A H2AA N3B 0.88 2.24 3.114(4) 171.7 . yes
N2A H2AB Cl1 0.88 2.90 3.619(3) 140.0 . yes
O1W H1WA Cl5 0.855(17) 2.77(3) 3.480(3) 141(4) 6_565 yes
O1W H1WB Cl2 0.866(18) 2.57(2) 3.395(4) 159(4) . yes

_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 1.115
_oxdiff_exptl_absorpt_empirical_full_min 0.911
####################################################################### 
# 
# 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_2a4mprmbicl
_database_code_depnum_ccdc_archive 'CCDC 2023493'
loop_
_audit_author_name
_audit_author_address
'Magdalena Owczarek'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Cl5, 2(C5 H8 N3), H2 O'
_chemical_formula_sum            'C10 H18 Bi Cl5 N6 O'
_chemical_formula_weight         624.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H18 N6 Bi Cl5 O '
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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.586(3)
_cell_length_b                   18.595(6)
_cell_length_c                   8.970(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.66(2)
_cell_angle_gamma                90
_cell_volume                     931.7(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5615
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.6950
_cell_measurement_theta_min      3.1550
_shelx_estimated_absorpt_T_max   0.310
_shelx_estimated_absorpt_T_min   0.113
_exptl_absorpt_coefficient_mu    10.190
_exptl_absorpt_correction_T_max  0.354
_exptl_absorpt_correction_T_min  0.139
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 13 0.1421
-8 0 -3 0.0807
2 20 -8 0.1209
3 -16 -9 0.1674
7 8 -3 0.0963
4 -21 4 0.0820
-2 -20 8 0.1209
8 -8 -1 0.1010
-7 10 3 0.0303
2 26 0 0.1232
-2 -26 0 0.1232
0 0 -13 0.1421

_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
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 0.0005 12.9999 -0.3935 0.4540 0.8345
-7.9997 0.0000 -3.0002 0.7714 0.6425 -0.2928
2.0000 19.9993 -7.9997 0.5607 -0.8525 -0.0482
2.9998 -16.0000 -8.9999 -0.3738 -0.2854 -0.8924
6.9998 7.9996 -2.9997 -0.3092 -0.9131 0.0712
3.9997 -20.9995 3.9999 -0.9746 0.1717 -0.1554
-2.0000 -19.9993 7.9997 -0.5607 0.8525 0.0482
7.9996 -8.0000 -0.9998 -0.8458 -0.6276 -0.1401
-6.9997 10.0000 2.9998 0.7491 0.5654 0.3250
2.0000 25.9994 0.0002 0.4652 -0.6890 0.5974
-2.0000 -25.9994 -0.0002 -0.4652 0.6890 -0.5974
0.0000 -0.0005 -12.9999 0.3935 -0.4540 -0.8345

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6440
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.736
_diffrn_reflns_theta_min         3.156
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  60.75   0.75    7.00    --   30.00 -79.00   0.00  153
  2  ω    -54.00  60.75   0.75    7.00    --   30.00 -79.00  90.00  153
  3  ω    -54.00  60.75   0.75    7.00    --   30.00 -79.00 180.00  153
  4  ω    -54.00  54.75   0.75    7.00    --   30.00 -79.00 270.00  145
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0850785000
_diffrn_orient_matrix_UB_12      0.0244374000
_diffrn_orient_matrix_UB_13      -0.0302734000
_diffrn_orient_matrix_UB_21      -0.0934122000
_diffrn_orient_matrix_UB_22      -0.0193166000
_diffrn_orient_matrix_UB_23      0.0349211000
_diffrn_orient_matrix_UB_31      0.0125254000
_diffrn_orient_matrix_UB_32      0.0220150000
_diffrn_orient_matrix_UB_33      0.0641914000
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2267
_reflns_number_total             2332
_reflns_odcompleteness_completeness 99.70
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.749
_refine_diff_density_min         -1.260
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         2332
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0226
_refine_ls_restrained_S_all      1.065
_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)+(0.0331P)²+0.4896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0561
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O1W-H1WA = O1W-H1WB
 0.88 with sigma of 0.02
 H1WB-H1WA
 1.44 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C5(H5)
3.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Bi Bi 0.40830(2) 0.250000 -0.53192(2) 0.00957(7) Uani 1 2 d S T P . .
Cl2 Cl 0.4456(2) 0.250000 -0.81757(11) 0.0142(2) Uani 1 2 d S T P . .
Cl4 Cl 0.4300(2) 0.250000 -0.21054(12) 0.0141(2) Uani 1 2 d S T P . .
Cl1 Cl 0.39590(13) 0.10711(5) -0.54420(8) 0.01658(17) Uani 1 1 d . . . . .
Cl3 Cl -0.0629(2) 0.250000 -0.53370(14) 0.0269(3) Uani 1 2 d S T P . .
N1 N 0.0410(5) 0.38257(14) 0.1187(3) 0.0143(5) Uani 1 1 d . . . . .
H1 H 0.032659 0.338643 0.082520 0.017 Uiso 1 1 calc R . . . .
N2 N 0.3782(5) 0.40402(17) -0.0236(3) 0.0162(6) Uani 1 1 d . . . . .
H2A H 0.491866 0.433041 -0.054364 0.019 Uiso 1 1 calc R . . . .
H2B H 0.369296 0.359822 -0.058323 0.019 Uiso 1 1 calc R . . . .
N3 N 0.2373(5) 0.49481(14) 0.1265(3) 0.0125(5) Uani 1 1 d . . . . .
C6 C -0.1249(6) 0.40508(18) 0.2174(4) 0.0154(6) Uani 1 1 d . . . . .
H6 H -0.249624 0.373623 0.247031 0.019 Uiso 1 1 calc R . . . .
C2 C 0.2198(6) 0.42697(17) 0.0752(3) 0.0127(6) Uani 1 1 d . . . . .
C4 C 0.0770(6) 0.51719(17) 0.2252(3) 0.0139(6) Uani 1 1 d . . . . .
C7 C 0.1053(6) 0.59166(18) 0.2833(4) 0.0177(7) Uani 1 1 d . . . . .
H7A H 0.200605 0.590664 0.375660 0.027 Uiso 1 1 calc GR . . . .
H7B H -0.052810 0.612089 0.303443 0.027 Uiso 1 1 calc GR . . . .
H7C H 0.186622 0.621279 0.209047 0.027 Uiso 1 1 calc GR . . . .
C5 C -0.1123(6) 0.47310(18) 0.2739(4) 0.0157(6) Uani 1 1 d . . . . .
H5 H -0.226351 0.490106 0.343256 0.019 Uiso 1 1 calc R . . . .
O1W O -0.0527(6) 0.250000 -0.0379(4) 0.0176(7) Uani 1 2 d DS T P . .
H1WA H -0.198(4) 0.250000 -0.073(5) 0.026 Uiso 1 2 d DRS T P . .
H1WB H 0.053(6) 0.250000 -0.108(4) 0.026 Uiso 1 2 d DRS T P . .


_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
Bi Cl2 2.5732(15) . ?
Bi Cl4 2.8840(17) . ?
Bi Cl1 2.6601(12) . ?
Bi Cl1 2.6602(12) 4_565 ?
Bi Cl3 2.954(2) 1_655 ?
Bi Cl3 2.6322(19) . ?
N1 C6 1.355(4) . ?
N1 C2 1.357(4) . ?
N2 C2 1.330(4) . ?
N3 C2 1.346(4) . ?
N3 C4 1.333(4) . ?
C6 C5 1.364(5) . ?
C4 C7 1.487(5) . ?
C4 C5 1.411(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Bi Cl4 172.95(3) . . ?
Cl2 Bi Cl1 87.773(16) . 4_565 ?
Cl2 Bi Cl1 87.773(16) . . ?
Cl2 Bi Cl3 94.96(4) . . ?
Cl2 Bi Cl3 84.38(4) . 1_655 ?
Cl4 Bi Cl3 88.56(4) . 1_655 ?
Cl1 Bi Cl4 92.417(17) . . ?
Cl1 Bi Cl4 92.416(17) 4_565 . ?
Cl1 Bi Cl1 174.42(3) . 4_565 ?
Cl1 Bi Cl3 91.453(16) 4_565 1_655 ?
Cl1 Bi Cl3 91.452(16) . 1_655 ?
Cl3 Bi Cl4 92.09(4) . . ?
Cl3 Bi Cl1 88.520(16) . . ?
Cl3 Bi Cl1 88.520(16) . 4_565 ?
Cl3 Bi Cl3 179.34(5) . 1_655 ?
Bi Cl3 Bi 179.34(5) . 1_455 ?
C6 N1 C2 120.7(3) . . ?
C4 N3 C2 118.2(3) . . ?
N1 C6 C5 119.8(3) . . ?
N2 C2 N1 119.6(3) . . ?
N2 C2 N3 118.8(3) . . ?
N3 C2 N1 121.5(3) . . ?
N3 C4 C7 117.0(3) . . ?
N3 C4 C5 122.4(3) . . ?
C5 C4 C7 120.6(3) . . ?
C6 C5 C4 117.3(3) . . ?

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
_geom_hbond_publ_flag
N1 H1 O1W 0.88 2.02 2.882(3) 164.5 . yes
N2 H2A N3 0.88 2.13 3.008(4) 178.7 3_665 yes
N2 H2B Cl4 0.88 2.48 3.333(3) 162.8 . yes
O1W H1WA Cl4 0.870(19) 2.40(2) 3.263(4) 171(4) 1_455 yes
O1W H1WB Cl4 0.867(19) 2.31(2) 3.125(4) 157(4) . yes

_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 1.128
_oxdiff_exptl_absorpt_empirical_full_min 0.876
####################################################################### 
# 
# 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_2aprmsbcl_acentro
_database_code_depnum_ccdc_archive 'CCDC 2025386'
loop_
_audit_author_name
_audit_author_address
'Magdalena Owczarek'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl5 Sb, 2(C4 H6 N3)'
_chemical_formula_sum            'C8 H12 Cl5 N6 Sb'
_chemical_formula_weight         491.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H12 N6 Sb1 Cl5'
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'
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'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.713(3)
_cell_length_b                   14.125(5)
_cell_length_c                   10.254(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.65(2)
_cell_angle_gamma                90
_cell_volume                     796.8(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12171
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.0020
_cell_measurement_theta_min      3.5370
_shelx_estimated_absorpt_T_max   0.748
_shelx_estimated_absorpt_T_min   0.602
_exptl_absorpt_coefficient_mu    2.567
_exptl_absorpt_correction_T_max  0.806
_exptl_absorpt_correction_T_min  0.649
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             476
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-8 1 0 0.0695
-5 15 7 0.1145
4 12 7 0.0719
-1 -14 -9 0.0855
2 -11 11 0.0464
0 10 -12 0.0731
8 0 0 0.0431

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_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
-7.9999 1.0002 0.0002 -0.4971 0.0487 -0.9030
-5.0000 14.9997 6.9997 0.5025 0.0037 -0.8999
3.9999 11.9996 6.9994 0.9978 0.0027 0.1594
-0.9999 -13.9996 -8.9994 -0.9590 -0.0845 0.2175
2.0000 -10.9994 10.9995 0.2648 0.9023 0.4709
-0.0000 9.9994 -11.9995 -0.2122 -0.9481 -0.2274
7.9999 -0.0002 -0.0003 0.5312 -0.0774 0.8798

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14833
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.962
_diffrn_reflns_theta_min         2.884
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  70.62   0.73   10.00    --   30.00 -79.00   0.00  194
  2  ω    -71.00  70.62   0.73   10.00    --   30.00 -79.00  90.00  194
  3  ω    -71.00  70.62   0.73   10.00    --   30.00 -79.00 180.00  194
  4  ω    -71.00  70.62   0.73   10.00    --   30.00 -79.00 270.00  194
  5  ω    -54.00  60.61   0.73   16.00    --   48.00 -79.00  45.00  157
  6  ω    -54.00  60.61   0.73   16.00    --   48.00 -79.00 135.00  157
  7  ω    -54.00  60.61   0.73   16.00    --   48.00 -79.00 225.00  157
  8  ω    -54.00   5.86   0.73   16.00    --   48.00 -79.00 315.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0664068000
_diffrn_orient_matrix_UB_12      0.0341153000
_diffrn_orient_matrix_UB_13      0.0461142000
_diffrn_orient_matrix_UB_21      -0.0096713000
_diffrn_orient_matrix_UB_22      -0.0286905000
_diffrn_orient_matrix_UB_23      0.0551001000
_diffrn_orient_matrix_UB_31      0.1099808000
_diffrn_orient_matrix_UB_32      -0.0231659000
_diffrn_orient_matrix_UB_33      -0.0003563000
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.702
_reflns_number_gt                6240
_reflns_number_total             6494
_reflns_odcompleteness_completeness 99.82
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.402
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details 
;
 Flack x determined using 2564 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.396(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         6494
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0236
_refine_ls_restrained_S_all      1.081
_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)+(0.0257P)²+0.1531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0531
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3B(H3B), N1A(H1A), C6A(H6A), C4A(H4A), C5A(H5A), C6B(H6B), N1B(H1B), C4B(H4B)
2.b X=CH2 refined with riding coordinates:
 N2B(H2BA,H2BB), N2A(H2AA,H2AB)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Sb Sb 0.52377(3) 0.41308(3) 0.25867(2) 0.01119(4) Uani 1 1 d . . . . .
Cl4 Cl 0.47479(13) 0.58952(5) 0.16643(7) 0.01582(12) Uani 1 1 d . . . . .
Cl3 Cl 0.45928(13) 0.35130(5) 0.01438(7) 0.01722(13) Uani 1 1 d . . . . .
Cl2 Cl 0.53276(13) 0.23682(5) 0.33687(7) 0.01603(12) Uani 1 1 d . . . . .
Cl5 Cl 0.54244(14) 0.47106(5) 0.50516(7) 0.01731(13) Uani 1 1 d . . . . .
C3B C -0.1395(6) 0.6414(2) 0.9688(3) 0.0161(5) Uani 1 1 d . . . . .
H3B H -0.222024 0.670494 1.027231 0.019 Uiso 1 1 calc R . . . .
N2B N 0.2105(5) 0.5109(2) 0.7237(3) 0.0192(5) Uani 1 1 d . . . . .
H2BA H 0.182742 0.450943 0.701743 0.023 Uiso 1 1 calc R . . . .
H2BB H 0.315779 0.543223 0.692709 0.023 Uiso 1 1 calc R . . . .
Cl1 Cl 0.09290(10) 0.41371(7) 0.22416(6) 0.01716(10) Uani 1 1 d . . . A 1
N3A N 0.0658(5) 0.31258(19) 0.6478(3) 0.0163(5) Uani 1 1 d . . . . .
N1A N -0.1290(5) 0.16817(18) 0.6655(2) 0.0157(4) Uani 1 1 d . . . . .
H1A H -0.228565 0.135717 0.700617 0.019 Uiso 1 1 calc R . . . .
C2A C -0.0908(6) 0.2614(2) 0.6965(3) 0.0149(5) Uani 1 1 d . . . . .
C6A C -0.0170(6) 0.1242(2) 0.5817(3) 0.0162(5) Uani 1 1 d . . . . .
H6A H -0.045343 0.058861 0.561364 0.019 Uiso 1 1 calc R . . . .
C4A C 0.1727(6) 0.2695(2) 0.5641(3) 0.0160(5) Uani 1 1 d . . . . .
H4A H 0.280212 0.305506 0.527434 0.019 Uiso 1 1 calc R . . . .
N2A N -0.2065(5) 0.3027(2) 0.7774(3) 0.0199(5) Uani 1 1 d . . . . .
H2AA H -0.180476 0.362807 0.798768 0.024 Uiso 1 1 calc R . . . .
H2AB H -0.309262 0.269844 0.809789 0.024 Uiso 1 1 calc R . . . .
C5A C 0.1367(6) 0.1743(2) 0.5266(3) 0.0166(5) Uani 1 1 d . . . . .
H5A H 0.215426 0.145953 0.465822 0.020 Uiso 1 1 calc R . . . .
C6B C 0.0217(6) 0.6904(2) 0.9178(3) 0.0168(5) Uani 1 1 d . . . . .
H6B H 0.053091 0.755425 0.939188 0.020 Uiso 1 1 calc R . . . .
N1B N 0.1361(5) 0.64518(18) 0.8363(2) 0.0157(4) Uani 1 1 d . . . . .
H1B H 0.240831 0.676624 0.803755 0.019 Uiso 1 1 calc R . . . .
C4B C -0.1773(6) 0.5467(2) 0.9311(3) 0.0152(5) Uani 1 1 d . . . . .
H4B H -0.289218 0.511426 0.965545 0.018 Uiso 1 1 calc R . . . .
N3B N -0.0665(5) 0.50267(18) 0.8501(2) 0.0154(4) Uani 1 1 d . . . . .
C2B C 0.0936(6) 0.5526(2) 0.8035(3) 0.0149(5) Uani 1 1 d . . . . .


_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
Sb Cl4 2.6536(12) . ?
Sb Cl3 2.5834(12) . ?
Sb Cl2 2.6119(12) . ?
Sb Cl5 2.6315(12) . ?
Sb Cl1 2.3905(14) . ?
C3B C6B 1.364(4) . ?
C3B C4B 1.394(4) . ?
N2B C2B 1.325(4) . ?
N3A C2A 1.347(4) . ?
N3A C4A 1.328(4) . ?
N1A C2A 1.359(4) . ?
N1A C6A 1.353(4) . ?
C2A N2A 1.327(4) . ?
C6A C5A 1.363(4) . ?
C4A C5A 1.398(4) . ?
C6B N1B 1.352(4) . ?
N1B C2B 1.355(4) . ?
C4B N3B 1.327(4) . ?
N3B C2B 1.341(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl3 Sb Cl4 89.88(3) . . ?
Cl3 Sb Cl2 87.80(3) . . ?
Cl3 Sb Cl5 174.07(3) . . ?
Cl2 Sb Cl4 174.97(3) . . ?
Cl2 Sb Cl5 90.54(3) . . ?
Cl5 Sb Cl4 91.32(3) . . ?
Cl1 Sb Cl4 86.47(3) . . ?
Cl1 Sb Cl3 89.19(3) . . ?
Cl1 Sb Cl2 89.04(3) . . ?
Cl1 Sb Cl5 85.08(3) . . ?
C6B C3B C4B 116.8(3) . . ?
C4A N3A C2A 117.4(3) . . ?
C6A N1A C2A 121.4(3) . . ?
N3A C2A N1A 120.9(3) . . ?
N2A C2A N3A 119.3(3) . . ?
N2A C2A N1A 119.8(3) . . ?
N1A C6A C5A 119.5(3) . . ?
N3A C4A C5A 124.0(3) . . ?
C6A C5A C4A 116.7(3) . . ?
N1B C6B C3B 119.1(3) . . ?
C6B N1B C2B 121.7(3) . . ?
N3B C4B C3B 124.0(3) . . ?
C4B N3B C2B 117.6(3) . . ?
N2B C2B N1B 119.7(3) . . ?
N2B C2B N3B 119.5(3) . . ?
N3B C2B N1B 120.8(3) . . ?

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
_geom_hbond_publ_flag
N2B H2BA N3A 0.88 2.09 2.965(4) 172.0 . yes
N2B H2BB Cl2 0.88 2.91 3.635(3) 141.0 2_656 yes
N1A H1A Cl4 0.88 2.30 3.154(3) 163.0 2_546 yes
N2A H2AA N3B 0.88 2.10 2.976(4) 171.8 . yes
N2A H2AB Cl4 0.88 2.75 3.496(3) 143.3 2_546 yes
N1B H1B Cl2 0.88 2.34 3.197(3) 164.2 2_656 yes

_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 1.125
_oxdiff_exptl_absorpt_empirical_full_min 0.923
####################################################################### 
# 
# 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_2shprmbicl
_database_code_depnum_ccdc_archive 'CCDC 2023490'
loop_
_audit_author_name
_audit_author_address
'Magdalena Owczarek'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Cl5, 2(C4 H5 N2 S)'
_chemical_formula_sum            'C8 H10 Bi Cl5 N4 S2'
_chemical_formula_weight         612.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H10 N4 S2 Bi Cl5'
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'
S S 0.1246 0.1234 '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                   5.500(4)
_cell_length_b                   15.082(5)
_cell_length_c                   10.360(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.39(2)
_cell_angle_gamma                90
_cell_volume                     832.4(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8313
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.5330
_cell_measurement_theta_min      4.9500
_shelx_estimated_absorpt_T_max   0.313
_shelx_estimated_absorpt_T_min   0.204
_exptl_absorpt_coefficient_mu    11.636
_exptl_absorpt_correction_T_max  0.319
_exptl_absorpt_correction_T_min  0.178
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             572
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -13 -4 0.0977
8 0 -7 0.0863
4 13 6 0.0688
0 5 14 0.0494
0 -15 -10 0.0785
2 13 -12 0.0760
-2 -13 12 0.0760
2 -16 8 0.0822
-2 16 -8 0.0822
-8 0 7 0.0863
-1 18 8 0.0423

_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
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
-5.0006 -12.9995 -3.9998 0.4039 0.8897 0.1899
8.0007 -0.0019 -7.0013 -1.0450 -0.1599 0.0108
4.0006 12.9996 6.0000 -0.2459 -0.9313 -0.1489
0.0003 4.9989 14.0005 0.3583 -0.8933 0.3296
-0.0002 -15.0008 -10.0007 -0.2958 0.9297 0.2142
2.0001 13.0026 -12.0002 -0.4654 0.1889 -0.8941
-2.0001 -13.0026 12.0002 0.4654 -0.1889 0.8941
2.0003 -16.0039 7.9994 -0.0798 -0.1649 0.9988
-2.0003 16.0039 -7.9994 0.0798 0.1649 -0.9988
-8.0007 0.0019 7.0013 1.0450 0.1599 -0.0108
-0.9999 18.0018 8.0009 0.3669 -0.8291 -0.4417

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16766
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         38.504
_diffrn_reflns_theta_min         4.685
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.971
_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   30.00   0.00  29.00 -20.00    --   270
  2  ω    -40.00  75.00   1.00   65.00    --   40.00 -79.00   0.00  115
  3  ω    -40.00  75.00   1.00   65.00    --   40.00 -79.00 120.00  115
  4  ω    -40.00  75.00   1.00   65.00    --   40.00 -79.00 240.00  115
;
_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      -0.1093141000
_diffrn_orient_matrix_UB_12      0.0034894000
_diffrn_orient_matrix_UB_13      0.0243452000
_diffrn_orient_matrix_UB_21      -0.0678493000
_diffrn_orient_matrix_UB_22      -0.0255146000
_diffrn_orient_matrix_UB_23      -0.0546922000
_diffrn_orient_matrix_UB_31      0.0342387000
_diffrn_orient_matrix_UB_32      -0.0393414000
_diffrn_orient_matrix_UB_33      0.0375888000
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3732
_reflns_number_total             4549
_reflns_odcompleteness_completeness 99.20
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.482
_refine_diff_density_min         -1.448
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         4549
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0189
_refine_ls_restrained_S_all      1.019
_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)+(0.0123P)²+0.5377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0348
_refine_ls_wR_factor_ref         0.0373
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-H1 = N3-H3
 0.88 with sigma of 0.02
3.a Riding coordinates:
 N1(H1), N3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_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
Bi Bi 1.000000 0.500000 0.500000 0.00849(2) Uani 1 2 d S T P . .
Cl3 Cl 1.03810(8) 0.66898(3) 0.58450(4) 0.01413(7) Uani 1 1 d . . . . .
Cl2 Cl 0.85688(9) 0.55524(3) 0.24932(4) 0.01817(8) Uani 1 1 d . . . . .
Cl1 Cl 0.500000 0.500000 0.500000 0.02538(13) Uani 1 2 d S T P . .
C6 C 0.3750(3) 0.35921(11) 0.18920(17) 0.0140(3) Uani 1 1 d . . . . .
H6 H 0.519409 0.394298 0.225220 0.017 Uiso 1 1 calc R . . . .
N1 N 0.1692(3) 0.39685(9) 0.11116(14) 0.0132(2) Uani 1 1 d D . . . .
H1 H 0.175039 0.453164 0.096303 0.030(7) Uiso 1 1 d DR . . . .
C5 C 0.3776(3) 0.26966(11) 0.21728(17) 0.0146(3) Uani 1 1 d . . . . .
H5 H 0.520634 0.241908 0.273130 0.017 Uiso 1 1 calc R . . . .
N3 N -0.0369(3) 0.26311(9) 0.08346(14) 0.0132(2) Uani 1 1 d D . . . .
H3 H -0.172580 0.235199 0.049919 0.031(7) Uiso 1 1 d DR . . . .
C4 C 0.1631(3) 0.22234(11) 0.16055(17) 0.0150(3) Uani 1 1 d . . . . .
H4 H 0.157365 0.160421 0.176324 0.018 Uiso 1 1 calc R . . . .
C2 C -0.0476(3) 0.35233(11) 0.05412(16) 0.0123(3) Uani 1 1 d . . . . .
S S -0.30191(8) 0.39901(3) -0.04159(4) 0.01411(7) Uani 1 1 d . . . . .


_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
Bi Cl3 2.6859(9) 3_766 ?
Bi Cl3 2.6859(9) . ?
Bi Cl2 2.6537(10) 3_766 ?
Bi Cl2 2.6538(10) . ?
Bi Cl1 2.750(2) 1_655 ?
Bi Cl1 2.750(2) . ?
C6 N1 1.343(2) . ?
C6 C5 1.381(2) . ?
N1 C2 1.368(2) . ?
C5 C4 1.379(3) . ?
N3 C4 1.338(2) . ?
N3 C2 1.378(2) . ?
C2 S 1.6570(19) . ?

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
Cl3 Bi Cl3 180.0 . 3_766 ?
Cl3 Bi Cl1 90.171(11) . 1_655 ?
Cl3 Bi Cl1 90.171(11) 3_766 . ?
Cl3 Bi Cl1 89.829(11) 3_766 1_655 ?
Cl3 Bi Cl1 89.829(11) . . ?
Cl2 Bi Cl3 89.93(2) . 3_766 ?
Cl2 Bi Cl3 90.07(2) 3_766 3_766 ?
Cl2 Bi Cl3 90.07(2) . . ?
Cl2 Bi Cl3 89.93(2) 3_766 . ?
Cl2 Bi Cl2 180.0 3_766 . ?
Cl2 Bi Cl1 86.94(3) 3_766 1_655 ?
Cl2 Bi Cl1 86.94(3) . . ?
Cl2 Bi Cl1 93.06(3) 3_766 . ?
Cl2 Bi Cl1 93.06(3) . 1_655 ?
Cl1 Bi Cl1 180.0 1_655 . ?
Bi Cl1 Bi 180.0 1_455 . ?
N1 C6 C5 120.23(16) . . ?
C6 N1 C2 124.51(15) . . ?
C4 C5 C6 116.96(16) . . ?
C4 N3 C2 124.35(15) . . ?
N3 C4 C5 120.41(16) . . ?
N1 C2 N3 113.53(14) . . ?
N1 C2 S 124.43(13) . . ?
N3 C2 S 122.04(13) . . ?

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
_geom_hbond_publ_flag
N1 H1 S 0.87 2.44 3.2852(18) 164.1 3_565 yes
N3 H3 Cl3 0.85 2.36 3.203(2) 168.4 2_545 yes

_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 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.825
####################################################################### 
# 
# 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_2aprmsbbr
_database_code_depnum_ccdc_archive 'CCDC 2025387'
loop_
_audit_author_name
_audit_author_address
'Magdalena Owczarek'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br5 Sb, 2(C4 H6 N3)'
_chemical_formula_sum            'C8 H12 Br5 N6 Sb'
_chemical_formula_weight         713.54
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H12 N6 Sb1 Br5'
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'
Br Br -0.2901 2.4595 '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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.946(3)
_cell_length_b                   14.401(4)
_cell_length_c                   10.621(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.31(2)
_cell_angle_gamma                90
_cell_volume                     877.2(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5599
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.5550
_cell_measurement_theta_min      4.8790
_shelx_estimated_absorpt_T_max   0.357
_shelx_estimated_absorpt_T_min   0.231
_exptl_absorpt_coefficient_mu    12.959
_exptl_absorpt_correction_T_max  0.416
_exptl_absorpt_correction_T_min  0.265
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.701
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -9 -13 0.0495
0 12 -12 0.0589
1 9 13 0.0495
0 -11 12 0.0437
-8 3 -2 0.0505
8 -2 1 0.0688
1 17 7 0.0666
1 -19 -5 0.0618
8 6 -4 0.0552

_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
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
-0.9998 -9.0010 -13.0023 -0.7843 -0.1941 0.6546
-0.0004 12.0023 -12.0016 0.1731 0.0425 1.0040
0.9998 9.0010 13.0023 0.7843 0.1941 -0.6546
0.0003 -11.0022 12.0017 -0.1290 -0.0370 -0.9828
-8.0013 2.9997 -2.0007 0.0686 -0.9428 0.4460
8.0013 -1.9995 1.0005 -0.0542 0.9464 -0.3623
0.9995 17.0025 7.0016 0.9592 0.2263 -0.1103
1.0008 -19.0027 -5.0012 -0.9869 0.0054 -0.1214
8.0010 6.0019 -4.0001 0.1504 0.9806 0.1194

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7214
_diffrn_reflns_point_group_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.693
_diffrn_reflns_theta_min         4.689
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    170.00 270.00   1.00   30.00   0.00  28.00   0.00    --   100
  2  ω    -60.00  84.00   1.00   50.00    --   40.00 -79.00   0.00  144
  3  ω    -60.00  74.00   1.00   50.00    --   40.00 -79.00 120.00  134
;
_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      0.0005406000
_diffrn_orient_matrix_UB_12      0.0441432000
_diffrn_orient_matrix_UB_13      0.0297189000
_diffrn_orient_matrix_UB_21      0.1194085000
_diffrn_orient_matrix_UB_22      0.0054905000
_diffrn_orient_matrix_UB_23      0.0019474000
_diffrn_orient_matrix_UB_31      -0.0321859000
_diffrn_orient_matrix_UB_32      0.0211431000
_diffrn_orient_matrix_UB_33      -0.0625068000
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.616
_reflns_Friedel_fraction_full    0.683
_reflns_Friedel_fraction_max     0.635
_reflns_number_gt                3442
_reflns_number_total             3618
_reflns_odcompleteness_completeness 96.77
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.057
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details 
;
 Flack x determined using 1241 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.446(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0226
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0142P)²+1.3770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0498
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1A(H1A), C5A(H5A), C6A(H6A), C4A(H4A), N1B(H1B), C4B(H4B), C5B(H5B), C6B(H6B)
2.b X=CH2 refined with riding coordinates:
 N2A(H2AA,H2AB), N2B(H2BA,H2BB)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Br2 Br 0.97942(13) 0.58984(4) -0.33746(7) 0.01434(16) Uani 1 1 d . . . . .
Br3 Br 0.94705(12) 0.34652(5) -0.50849(7) 0.01563(15) Uani 1 1 d . . . . .
Sb Sb 0.99304(7) 0.40733(7) -0.25456(4) 0.01007(8) Uani 1 1 d . . . . .
Br5 Br 1.05402(12) 0.46920(5) -0.00182(7) 0.01544(15) Uani 1 1 d . . . . .
Br4 Br 1.01435(12) 0.22360(4) -0.16533(7) 0.01408(16) Uani 1 1 d . . . . .
Br1 Br 1.43470(10) 0.40288(6) -0.22328(6) 0.01649(13) Uani 1 1 d . . . . .
N3A N 0.5691(12) 0.3172(4) 0.1541(6) 0.0145(14) Uani 1 1 d . . . . .
N2A N 0.3065(12) 0.3085(5) 0.2799(7) 0.0211(16) Uani 1 1 d . . . . .
H2AA H 0.205575 0.277429 0.311093 0.025 Uiso 1 1 calc R . . . .
H2AB H 0.337713 0.366838 0.302214 0.025 Uiso 1 1 calc R . . . .
N1A N 0.3665(11) 0.1788(5) 0.1643(6) 0.0158(14) Uani 1 1 d . . . . .
H1A H 0.265391 0.148032 0.195710 0.019 Uiso 1 1 calc R . . . .
C2A C 0.4110(13) 0.2674(5) 0.1996(7) 0.0146(16) Uani 1 1 d . . . . .
C5A C 0.6260(13) 0.1804(6) 0.0344(7) 0.0160(16) Uani 1 1 d . . . . .
H5A H 0.703109 0.151724 -0.023202 0.019 Uiso 1 1 calc R . . . .
C6A C 0.4710(13) 0.1341(6) 0.0817(7) 0.0169(17) Uani 1 1 d . . . . .
H6A H 0.434480 0.071115 0.058188 0.020 Uiso 1 1 calc R . . . .
C4A C 0.6691(13) 0.2728(5) 0.0735(7) 0.0157(16) Uani 1 1 d . . . . .
H4A H 0.778034 0.306409 0.039922 0.019 Uiso 1 1 calc R . . . .
N3B N 0.4356(12) 0.5054(5) 0.3500(7) 0.0162(14) Uani 1 1 d . . . . .
N2B N 0.6933(12) 0.5146(5) 0.2209(6) 0.0189(15) Uani 1 1 d . . . . .
H2BA H 0.665887 0.455852 0.199231 0.023 Uiso 1 1 calc R . . . .
H2BB H 0.791676 0.546650 0.189107 0.023 Uiso 1 1 calc R . . . .
N1B N 0.6280(11) 0.6453(4) 0.3337(6) 0.0149(13) Uani 1 1 d . . . . .
H1B H 0.724422 0.676606 0.299456 0.018 Uiso 1 1 calc R . . . .
C2B C 0.5857(14) 0.5549(6) 0.3019(8) 0.0159(16) Uani 1 1 d . . . . .
C4B C 0.3361(13) 0.5476(5) 0.4319(7) 0.0152(16) Uani 1 1 d . . . . .
H4B H 0.230735 0.512778 0.466635 0.018 Uiso 1 1 calc R . . . .
C5B C 0.3761(13) 0.6407(5) 0.4709(8) 0.0164(16) Uani 1 1 d . . . . .
H5B H 0.303757 0.668714 0.531124 0.020 Uiso 1 1 calc R . . . .
C6B C 0.5262(14) 0.6884(5) 0.4164(7) 0.0154(16) Uani 1 1 d . . . . .
H6B H 0.558394 0.751996 0.437206 0.018 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
Br2 Sb 2.7662(14) . ?
Br3 Sb 2.7796(13) . ?
Sb Br5 2.7599(13) . ?
Sb Br4 2.8021(14) . ?
Sb Br1 2.5594(15) . ?
N3A C2A 1.368(9) . ?
N3A C4A 1.328(9) . ?
N2A C2A 1.320(9) . ?
N1A C2A 1.337(10) . ?
N1A C6A 1.363(9) . ?
C5A C6A 1.338(11) . ?
C5A C4A 1.398(11) . ?
N3B C2B 1.344(9) . ?
N3B C4B 1.322(9) . ?
N2B C2B 1.333(9) . ?
N1B C2B 1.352(10) . ?
N1B C6B 1.343(9) . ?
C4B C5B 1.404(11) . ?
C5B C6B 1.370(10) . ?

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
Br2 Sb Br3 90.19(3) . . ?
Br2 Sb Br4 178.70(3) . . ?
Br3 Sb Br4 90.84(4) . . ?
Br5 Sb Br2 89.32(4) . . ?
Br5 Sb Br3 178.09(3) . . ?
Br5 Sb Br4 89.61(3) . . ?
Br1 Sb Br2 90.46(3) . . ?
Br1 Sb Br3 87.29(3) . . ?
Br1 Sb Br5 90.86(3) . . ?
Br1 Sb Br4 88.81(3) . . ?
C4A N3A C2A 116.3(7) . . ?
C2A N1A C6A 122.8(6) . . ?
N2A C2A N3A 118.6(7) . . ?
N2A C2A N1A 121.1(6) . . ?
N1A C2A N3A 120.3(7) . . ?
C6A C5A C4A 117.0(7) . . ?
C5A C6A N1A 118.8(8) . . ?
N3A C4A C5A 124.8(7) . . ?
C4B N3B C2B 117.6(7) . . ?
C6B N1B C2B 121.5(6) . . ?
N3B C2B N1B 120.9(6) . . ?
N2B C2B N3B 119.7(8) . . ?
N2B C2B N1B 119.4(7) . . ?
N3B C4B C5B 124.2(7) . . ?
C6B C5B C4B 115.6(7) . . ?
N1B C6B C5B 120.1(7) . . ?

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
_geom_hbond_publ_flag
N2A H2AA Br2 0.88 2.96 3.705(7) 143.8 2_645 yes
N2A H2AB N3B 0.88 2.10 2.981(9) 175.5 . yes
N1A H1A Br2 0.88 2.50 3.354(6) 164.1 2_645 yes
N2B H2BA N3A 0.88 2.10 2.975(9) 174.1 . yes
N2B H2BB Br4 0.88 2.84 3.602(7) 146.5 2_755 yes
N1B H1B Br4 0.88 2.46 3.317(6) 163.5 2_755 yes

_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 1.109
_oxdiff_exptl_absorpt_empirical_full_min 0.931
####################################################################### 
# 
# 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_2apyrimabs
_database_code_depnum_ccdc_archive 'CCDC 2025389'
loop_
_audit_author_name
_audit_author_address
'Magdalena Owczarek'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT973_2apyrimabs          
;
PROBLEM: Check Calcd Positive Resid. Density on Bi 2.14 eA-3
RESPONSE: Due to the high absorption coefficient (20mm-1), even the analytical numeric absorption correction using a multifaceted crystal model is not efficient. As a consequence, an additional residual density maximum around heavy metal ion appears. It is not a result of twinning, unassigned atoms, or errors in the model.
;
# end Validation Reply Form

_audit_creation_date             2020-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Br5, 2(C4 H6 N3)'
_chemical_formula_sum            'C8 H12 Bi Br5 N6'
_chemical_formula_weight         800.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H12 Bi Br5 N6'
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'
Br Br -0.2901 2.4595 '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'

_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                   7.8733(3)
_cell_length_b                   11.4038(5)
_cell_length_c                   11.6180(5)
_cell_angle_alpha                115.801(5)
_cell_angle_beta                 96.295(3)
_cell_angle_gamma                98.857(3)
_cell_volume                     909.46(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5859
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.5440
_cell_measurement_theta_min      3.3250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    20.675
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_correction_T_min  0.035
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.924
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 -1 0.0192
-1 -1 1 0.0192
0 -1 0 0.0483
0 1 0 0.0483
0 0 1 0.0979
0 0 -1 0.1449
3 -5 2 0.0968
-2 5 -3 0.1150

_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.038
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
1.0000 1.0000 -1.0000 -0.0332 0.0634 0.0962
-1.0000 -1.0000 1.0000 0.0332 -0.0634 -0.0962
0.0000 -1.0000 -0.0000 0.0588 -0.0396 0.0021
-0.0000 1.0000 0.0000 -0.0588 0.0396 -0.0021
0.0000 0.0000 1.0000 -0.0598 -0.0325 -0.0122
-0.0000 -0.0000 -1.0000 0.0598 0.0325 0.0122
3.0000 -5.0000 2.0000 0.0717 -0.2889 0.2443
-2.0000 5.0000 -3.0000 -0.0461 0.3127 -0.1460

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.567
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9692
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.567
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.673
_diffrn_reflns_theta_min         2.972
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.567
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  69.50   0.75   30.00    --   28.00 -79.00   0.00  186
  2  ω    -70.00  69.50   0.75   30.00    --   28.00 -79.00  90.00  186
  3  ω    -70.00  69.50   0.75   30.00    --   28.00 -79.00 180.00  186
  4  ω    -70.00  69.50   0.75   30.00    --   28.00 -79.00 270.00  186
  5  ω    -54.00  60.00   0.75   50.00    --   48.00 -79.00  45.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0342251000
_diffrn_orient_matrix_UB_12      -0.0588107000
_diffrn_orient_matrix_UB_13      -0.0598369000
_diffrn_orient_matrix_UB_21      -0.0087018000
_diffrn_orient_matrix_UB_22      0.0395608000
_diffrn_orient_matrix_UB_23      -0.0325141000
_diffrn_orient_matrix_UB_31      0.0860660000
_diffrn_orient_matrix_UB_32      -0.0021123000
_diffrn_orient_matrix_UB_33      -0.0122301000
_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                4358
_reflns_number_total             5132
_reflns_odcompleteness_completeness 99.22
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.716
_refine_diff_density_min         -2.757
_refine_diff_density_rms         0.400
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         5132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0756P)²+5.6399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1499
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1A(H1A), C5A(H5A), N1B(H1B), C6A(H6A), C4A(H4A), C6B(H6B), C4B(H4B), C5B(H5B)
2.b X=CH2 refined with riding coordinates:
 N2A(H2AA,H2AB), N2B(H2BA,H2BB)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Bi Bi 0.53421(4) 0.17160(3) 0.69515(2) 0.01589(12) Uani 1 1 d . . . . .
Br5 Br 0.29628(12) 0.27251(9) 0.85852(8) 0.0201(2) Uani 1 1 d . . . . .
Br3 Br 0.76511(12) 0.05453(9) 0.51492(8) 0.0212(2) Uani 1 1 d . . . . .
Br4 Br 0.47705(13) 0.33987(9) 0.56548(8) 0.0219(2) Uani 1 1 d . . . . .
Br1 Br 0.82137(12) 0.36133(9) 0.86152(7) 0.0227(2) Uani 1 1 d . . . . .
Br2 Br 0.57962(13) 0.01698(10) 0.81647(8) 0.0235(2) Uani 1 1 d . . . . .
N1A N 1.2157(10) 0.5027(8) 0.7820(6) 0.0224(16) Uani 1 1 d . . . . .
H1A H 1.184842 0.437881 0.802635 0.027 Uiso 1 1 calc R . . . .
N2A N 0.9944(11) 0.3922(8) 0.5963(6) 0.0215(16) Uani 1 1 d . . . . .
H2AA H 0.937361 0.385065 0.523211 0.026 Uiso 1 1 calc R . . . .
H2AB H 0.964660 0.329775 0.620283 0.026 Uiso 1 1 calc R . . . .
N3A N 1.1726(10) 0.5929(8) 0.6354(7) 0.0197(15) Uani 1 1 d . . . . .
C5A C 1.4021(13) 0.7100(10) 0.8308(8) 0.023(2) Uani 1 1 d . . . . .
H5A H 1.495214 0.785082 0.884841 0.028 Uiso 1 1 calc R . . . .
N2B N 1.0012(14) -0.0306(10) 0.7279(10) 0.039(2) Uani 1 1 d . . . . .
H2BA H 0.941085 -0.039941 0.654804 0.047 Uiso 1 1 calc R . . . .
H2BB H 1.087577 0.039850 0.774871 0.047 Uiso 1 1 calc R . . . .
N1B N 0.8308(11) -0.2299(9) 0.6965(8) 0.0282(19) Uani 1 1 d . . . . .
H1B H 0.771300 -0.238500 0.623483 0.034 Uiso 1 1 calc R . . . .
C6A C 1.3504(12) 0.6061(11) 0.8595(8) 0.024(2) Uani 1 1 d . . . . .
H6A H 1.411217 0.607717 0.935679 0.029 Uiso 1 1 calc R . . . .
C4A C 1.3039(13) 0.6947(10) 0.7135(8) 0.0220(19) Uani 1 1 d . . . . .
H4A H 1.334859 0.763263 0.688941 0.026 Uiso 1 1 calc R . . . .
N3B N 1.0615(12) -0.1052(9) 0.8787(7) 0.030(2) Uani 1 1 d . . . . .
C2A C 1.1256(12) 0.4971(9) 0.6704(7) 0.0173(17) Uani 1 1 d . . . . .
C2B C 0.9621(14) -0.1219(12) 0.7669(9) 0.028(2) Uani 1 1 d . . . . .
C6B C 0.7865(15) -0.3258(11) 0.7330(11) 0.031(2) Uani 1 1 d . . . . .
H6B H 0.693590 -0.401874 0.681611 0.037 Uiso 1 1 calc R . . . .
C4B C 1.0193(17) -0.1967(12) 0.9162(10) 0.037(3) Uani 1 1 d . . . . .
H4B H 1.086737 -0.185916 0.994567 0.045 Uiso 1 1 calc R . . . .
C5B C 0.8822(17) -0.3087(13) 0.8487(11) 0.038(3) Uani 1 1 d . . . . .
H5B H 0.854977 -0.371571 0.880897 0.045 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
Bi Br5 2.8246(9) . ?
Bi Br3 3.0902(10) 2_656 ?
Bi Br3 2.9361(9) . ?
Bi Br4 2.9644(10) . ?
Bi Br1 2.7247(9) . ?
Bi Br2 2.7333(10) . ?
N1A H1A 0.8800 . ?
N1A C6A 1.344(13) . ?
N1A C2A 1.379(11) . ?
N2A H2AA 0.8800 . ?
N2A H2AB 0.8800 . ?
N2A C2A 1.330(11) . ?
N3A C4A 1.322(12) . ?
N3A C2A 1.338(11) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.382(14) . ?
C5A C4A 1.416(12) . ?
N2B H2BA 0.8800 . ?
N2B H2BB 0.8800 . ?
N2B C2B 1.314(14) . ?
N1B H1B 0.8800 . ?
N1B C2B 1.342(14) . ?
N1B C6B 1.348(14) . ?
C6A H6A 0.9500 . ?
C4A H4A 0.9500 . ?
N3B C2B 1.360(13) . ?
N3B C4B 1.309(15) . ?
C6B H6B 0.9500 . ?
C6B C5B 1.384(16) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.389(18) . ?
C5B H5B 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
Br5 Bi Br3 176.79(3) . . ?
Br5 Bi Br3 91.11(3) . 2_656 ?
Br5 Bi Br4 91.52(3) . . ?
Br3 Bi Br3 85.68(3) . 2_656 ?
Br3 Bi Br4 88.58(3) . . ?
Br4 Bi Br3 89.10(3) . 2_656 ?
Br1 Bi Br5 95.09(3) . . ?
Br1 Bi Br3 173.77(3) . 2_656 ?
Br1 Bi Br3 88.12(3) . . ?
Br1 Bi Br4 90.16(3) . . ?
Br1 Bi Br2 90.44(3) . . ?
Br2 Bi Br5 87.25(3) . . ?
Br2 Bi Br3 90.44(3) . 2_656 ?
Br2 Bi Br3 92.62(3) . . ?
Br2 Bi Br4 178.67(3) . . ?
Bi Br3 Bi 94.32(3) . 2_656 ?
C6A N1A H1A 119.7 . . ?
C6A N1A C2A 120.6(8) . . ?
C2A N1A H1A 119.7 . . ?
H2AA N2A H2AB 120.0 . . ?
C2A N2A H2AA 120.0 . . ?
C2A N2A H2AB 120.0 . . ?
C4A N3A C2A 117.8(8) . . ?
C6A C5A H5A 123.0 . . ?
C6A C5A C4A 114.0(8) . . ?
C4A C5A H5A 123.0 . . ?
H2BA N2B H2BB 120.0 . . ?
C2B N2B H2BA 120.0 . . ?
C2B N2B H2BB 120.0 . . ?
C2B N1B H1B 118.7 . . ?
C2B N1B C6B 122.6(9) . . ?
C6B N1B H1B 118.7 . . ?
N1A C6A C5A 121.4(8) . . ?
N1A C6A H6A 119.3 . . ?
C5A C6A H6A 119.3 . . ?
N3A C4A C5A 125.4(9) . . ?
N3A C4A H4A 117.3 . . ?
C5A C4A H4A 117.3 . . ?
C4B N3B C2B 116.9(10) . . ?
N2A C2A N1A 118.4(8) . . ?
N2A C2A N3A 120.8(8) . . ?
N3A C2A N1A 120.8(8) . . ?
N2B C2B N1B 120.8(10) . . ?
N2B C2B N3B 118.0(10) . . ?
N1B C2B N3B 121.2(10) . . ?
N1B C6B H6B 121.4 . . ?
N1B C6B C5B 117.2(11) . . ?
C5B C6B H6B 121.4 . . ?
N3B C4B H4B 117.9 . . ?
N3B C4B C5B 124.2(11) . . ?
C5B C4B H4B 117.9 . . ?
C6B C5B C4B 117.8(10) . . ?
C6B C5B H5B 121.1 . . ?
C4B C5B H5B 121.1 . . ?

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
_geom_hbond_publ_flag
N1A H1A Br5 0.88 2.49 3.241(9) 143.7 1_655 yes
N2A H2AA N3A 0.88 2.08 2.949(10) 168.8 2_766 yes
N2A H2AB Br3 0.88 2.92 3.646(8) 140.8 . yes
N2B H2BA Br3 0.88 2.69 3.487(10) 152.0 . yes
N2B H2BB Br5 0.88 2.60 3.440(11) 160.7 1_655 yes
N1B H1B Br4 0.88 2.48 3.291(8) 154.3 2_656 yes

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.572
_oxdiff_exptl_absorpt_empirical_full_min 0.655
