# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_p21
_database_code_depnum_ccdc_archive 'CCDC 1918924'
loop_
_audit_author_name
_audit_author_address
'Anna Gagor'
;ILT SR PAS Wroclaw Poland
Poland
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2019-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H20 Cl5 N2 Sb'
_chemical_formula_weight         443.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           ?

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

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

_cell_length_a                   8.4941(3)
_cell_length_b                   11.0389(6)
_cell_length_c                   17.5977(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90.100(10)
_cell_volume                     1650.05(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    149.9(2)
_cell_measurement_reflns_used    12927
_cell_measurement_theta_min      3.0120
_cell_measurement_theta_max      29.208


_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.461
_exptl_absorpt_correction_T_min  0.82435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.873
_oxdiff_exptl_absorpt_empirical_full_max 1.117
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      149.9(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            14800
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.398
_diffrn_reflns_theta_max         25.670
_diffrn_reflns_theta_full        25.670
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             6038
_reflns_number_gt                5974
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_max     0.935
_reflns_Friedel_fraction_full    0.935

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0130P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2673 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.278(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6038
_refine_ls_number_parameters     290
_refine_ls_number_restraints     161
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_ref         0.0362
_refine_ls_wR_factor_gt          0.0359
_refine_ls_goodness_of_fit_ref   0.832
_refine_ls_restrained_S_all      0.846
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.28319(5) 0.95105(4) -0.27537(2) 0.02338(10) Uani 1 1 d . . . . .
Sb2 Sb 0.80067(5) 0.63434(4) -0.13389(2) 0.02266(10) Uani 1 1 d . . . . .
Cl10 Cl 0.05174(19) 1.02192(15) -0.34010(10) 0.0326(4) Uani 1 1 d . . . . .
Cl11 Cl 0.4416(2) 1.1057(2) -0.33592(12) 0.0533(6) Uani 1 1 d . . . . .
Cl12 Cl 0.56954(19) 0.52392(15) -0.08936(10) 0.0334(4) Uani 1 1 d . . . . .
Cl13 Cl 0.9781(2) 0.50127(18) -0.06500(12) 0.0459(5) Uani 1 1 d . . . . .
Cl20 Cl 0.3332(3) 0.8096(2) -0.38283(11) 0.0635(7) Uani 1 1 d . . . . .
Cl21 Cl 0.7783(2) 0.76937(15) -0.02461(10) 0.0367(4) Uani 1 1 d . . . . .
Cl31 Cl 0.8020(2) 0.46087(14) -0.26511(10) 0.0357(4) Uani 1 1 d . . . . .
Cl30 Cl 0.19551(19) 1.11980(13) -0.16442(8) 0.0293(3) Uani 1 1 d . . . . .
Cl40 Cl 0.0747(2) 0.78285(16) -0.18216(10) 0.0348(4) Uani 1 1 d . . . . .
Cl41 Cl 0.58395(18) 0.82099(14) -0.20349(9) 0.0266(4) Uani 1 1 d . . . . .
C1 C -0.3473(9) 0.6301(6) -0.4386(4) 0.0366(16) Uani 1 1 d . U . . .
H1A H -0.458916 0.628117 -0.450241 0.044 Uiso 1 1 calc R U . . .
H1B H -0.304343 0.549230 -0.443893 0.044 Uiso 1 1 calc R U . . .
C2 C -0.2611(9) 0.7197(6) -0.4890(4) 0.0452(18) Uani 1 1 d . U . . .
H2A H -0.231748 0.682561 -0.536868 0.054 Uiso 1 1 calc R U . . .
H2B H -0.325923 0.790125 -0.499190 0.054 Uiso 1 1 calc R U . . .
C3 C -0.1185(9) 0.7538(7) -0.4440(4) 0.0483(18) Uani 1 1 d . U . . .
H3A H -0.074429 0.829824 -0.461696 0.058 Uiso 1 1 calc R U . . .
H3B H -0.038537 0.691364 -0.447156 0.058 Uiso 1 1 calc R U . . .
C4 C -0.1813(9) 0.7655(6) -0.3635(4) 0.0385(17) Uani 1 1 d . U . . .
H4A H -0.101568 0.743080 -0.326669 0.046 Uiso 1 1 calc R U . . .
H4B H -0.215021 0.847871 -0.353352 0.046 Uiso 1 1 calc R U . . .
N5 N -0.3184(6) 0.6795(4) -0.3605(3) 0.0263(12) Uani 1 1 d . U . . .
H5A H -0.297634 0.619213 -0.328465 0.032 Uiso 1 1 calc R U . . .
H5B H -0.403772 0.718099 -0.343944 0.032 Uiso 1 1 calc R U . . .
C6 C 0.3412(11) 0.5099(9) -0.2846(5) 0.083(3) Uani 1 1 d . U . . .
H6A H 0.454458 0.508155 -0.277597 0.099 Uiso 1 1 calc R U . . .
H6B H 0.307141 0.593739 -0.284147 0.099 Uiso 1 1 calc R U . . .
C7 C 0.2641(10) 0.4432(7) -0.2238(5) 0.054(2) Uani 1 1 d . U . . .
H7A H 0.211849 0.498440 -0.189199 0.065 Uiso 1 1 calc R U . . .
H7B H 0.340354 0.396083 -0.195435 0.065 Uiso 1 1 calc R U . . .
N8 N 0.1484(6) 0.3630(5) -0.2609(3) 0.0383(14) Uani 1 1 d . U . . .
H8A H 0.159889 0.287440 -0.244138 0.046 Uiso 1 1 calc R U . . .
H8B H 0.051148 0.387306 -0.250117 0.046 Uiso 1 1 calc R U . . .
C9 C 0.1746(9) 0.3672(7) -0.3440(4) 0.0502(19) Uani 1 1 d . U . . .
H9A H 0.205875 0.288499 -0.363171 0.060 Uiso 1 1 calc R U . . .
H9B H 0.080118 0.393033 -0.370306 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3011(15) 0.4557(9) -0.3535(6) 0.098(3) Uani 1 1 d . U . . .
H10A H 0.267887 0.517631 -0.389101 0.118 Uiso 1 1 calc R U . . .
H10B H 0.392904 0.415764 -0.374499 0.118 Uiso 1 1 calc R U . . .
C11 C 0.7627(8) 0.1218(6) -0.2070(4) 0.0343(16) Uani 1 1 d . U . . .
H11A H 0.843918 0.173267 -0.228517 0.041 Uiso 1 1 calc R U . . .
H11B H 0.709136 0.079810 -0.248030 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6476(8) 0.1955(7) -0.1609(4) 0.0422(18) Uani 1 1 d . U . . .
H12A H 0.545907 0.155686 -0.157754 0.051 Uiso 1 1 calc R U . . .
H12B H 0.633861 0.275804 -0.182282 0.051 Uiso 1 1 calc R U . . .
C13 C 0.7259(11) 0.2015(7) -0.0843(4) 0.058(2) Uani 1 1 d . U . . .
H13A H 0.801466 0.267365 -0.082769 0.070 Uiso 1 1 calc R U . . .
H13B H 0.648223 0.214344 -0.044692 0.070 Uiso 1 1 calc R U . . .
C14 C 0.8081(10) 0.0809(6) -0.0730(4) 0.0438(18) Uani 1 1 d . U . . .
H14A H 0.908072 0.091913 -0.047323 0.053 Uiso 1 1 calc R U . . .
H14B H 0.743177 0.026086 -0.043425 0.053 Uiso 1 1 calc R U . . .
N15 N 0.8322(6) 0.0331(5) -0.1520(3) 0.0334(13) Uani 1 1 d . U . . .
H15A H 0.934566 0.023902 -0.161161 0.040 Uiso 1 1 calc R U . . .
H15B H 0.785486 -0.038722 -0.156894 0.040 Uiso 1 1 calc R U . . .
N16 N 0.3505(6) 0.7821(5) -0.0593(3) 0.0315(13) Uani 1 1 d . U . . .
H16A H 0.275098 0.780600 -0.094437 0.038 Uiso 1 1 calc R U . . .
H16B H 0.440018 0.756666 -0.080188 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3069(9) 0.7053(6) 0.0070(4) 0.0393(15) Uani 1 1 d . U . . .
H17A H 0.400061 0.678556 0.034095 0.047 Uiso 1 1 calc R U . . .
H17B H 0.247306 0.634830 -0.009089 0.047 Uiso 1 1 calc R U . . .
C18 C 0.2083(9) 0.7867(6) 0.0560(4) 0.0358(15) Uani 1 1 d . U . . .
H18A H 0.239817 0.779820 0.108808 0.043 Uiso 1 1 calc R U . . .
H18B H 0.097923 0.764908 0.051872 0.043 Uiso 1 1 calc R U . . .
C19 C 0.2350(8) 0.9144(6) 0.0275(4) 0.0382(17) Uani 1 1 d . U . . .
H19A H 0.262212 0.968042 0.069150 0.046 Uiso 1 1 calc R U . . .
H19B H 0.141340 0.945103 0.002601 0.046 Uiso 1 1 calc R U . . .
C20 C 0.3692(8) 0.9046(6) -0.0279(4) 0.0341(16) Uani 1 1 d . U . . .
H20A H 0.360970 0.965481 -0.067458 0.041 Uiso 1 1 calc R U . . .
H20B H 0.469761 0.913404 -0.002414 0.041 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Cl10 2.4042(16) . ?
Sb1 Cl11 2.4194(19) . ?
Sb1 Cl20 2.4893(19) . ?
Sb1 Cl30 2.8004(15) . ?
Sb1 Cl40 3.0433(18) . ?
Sb1 Cl41 3.1939(16) . ?
Sb2 Cl13 2.4306(18) . ?
Sb2 Cl12 2.4384(17) . ?
Sb2 Cl21 2.4406(17) . ?
Sb2 Cl40 2.9690(18) 1_655 ?
Sb2 Cl41 3.0244(16) . ?
C1 N5 1.499(8) . ?
C1 C2 1.516(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.494(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.520(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N5 1.502(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
C6 C7 1.453(10) . ?
C6 C10 1.394(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N8 1.475(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N8 C9 1.478(9) . ?
N8 H8A 0.8900 . ?
N8 H8B 0.8900 . ?
C9 C10 1.460(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.511(9) . ?
C11 N15 1.500(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.504(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.517(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N15 1.500(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N15 H15A 0.8900 . ?
N15 H15B 0.8900 . ?
N16 C17 1.490(8) . ?
N16 C20 1.469(8) . ?
N16 H16A 0.8900 . ?
N16 H16B 0.8900 . ?
C17 C18 1.501(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.513(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.504(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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
Cl10 Sb1 Cl11 90.91(6) . . ?
Cl10 Sb1 Cl20 89.12(6) . . ?
Cl11 Sb1 Cl20 90.73(9) . . ?
Cl10 Sb1 Cl30 83.99(5) . . ?
Cl11 Sb1 Cl30 89.19(6) . . ?
Cl20 Sb1 Cl30 173.10(6) . . ?
Cl10 Sb1 Cl40 88.78(5) . . ?
Cl11 Sb1 Cl40 171.99(7) . . ?
Cl20 Sb1 Cl40 97.26(7) . . ?
Cl30 Sb1 Cl40 82.82(5) . . ?
Cl10 Sb1 Cl41 171.54(5) . . ?
Cl11 Sb1 Cl41 92.71(6) . . ?
Cl20 Sb1 Cl41 83.20(6) . . ?
Cl30 Sb1 Cl41 103.70(4) . . ?
Cl40 Sb1 Cl41 88.70(5) . . ?
Cl13 Sb2 Cl12 92.14(6) . . ?
Cl13 Sb2 Cl21 91.44(7) . . ?
Cl12 Sb2 Cl21 89.35(6) . . ?
Cl13 Sb2 Cl40 89.42(6) . 1_655 ?
Cl12 Sb2 Cl40 176.19(6) . 1_655 ?
Cl21 Sb2 Cl40 87.14(6) . 1_655 ?
Cl13 Sb2 Cl41 173.02(6) . . ?
Cl12 Sb2 Cl41 88.86(5) . . ?
Cl21 Sb2 Cl41 81.66(5) . . ?
Cl40 Sb2 Cl41 89.17(5) 1_655 . ?
Sb2 Cl41 Sb1 162.73(6) . . ?
N5 C1 C2 102.8(5) . . ?
N5 C1 H1A 111.2 . . ?
C2 C1 H1A 111.2 . . ?
N5 C1 H1B 111.2 . . ?
C2 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
C3 C2 C1 104.2(6) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C2 C3 C4 103.3(6) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
N5 C4 C3 104.5(5) . . ?
N5 C4 H4A 110.8 . . ?
C3 C4 H4A 110.8 . . ?
N5 C4 H4B 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C1 N5 C4 108.9(5) . . ?
C1 N5 H5A 109.9 . . ?
C4 N5 H5A 109.9 . . ?
C1 N5 H5B 109.9 . . ?
C4 N5 H5B 109.9 . . ?
H5A N5 H5B 108.3 . . ?
C7 C6 C10 108.2(8) . . ?
C7 C6 H6A 110.1 . . ?
C10 C6 H6A 110.1 . . ?
C7 C6 H6B 110.1 . . ?
C10 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C6 C7 N8 106.1(7) . . ?
C6 C7 H7A 110.5 . . ?
N8 C7 H7A 110.5 . . ?
C6 C7 H7B 110.5 . . ?
N8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C9 N8 C7 108.6(6) . . ?
C9 N8 H8A 110.0 . . ?
C7 N8 H8A 110.0 . . ?
C9 N8 H8B 110.0 . . ?
C7 N8 H8B 110.0 . . ?
H8A N8 H8B 108.4 . . ?
C10 C9 N8 104.2(7) . . ?
C10 C9 H9A 110.9 . . ?
N8 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
N8 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C9 C10 C6 111.5(8) . . ?
C9 C10 H10A 109.3 . . ?
C6 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C6 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 N15 105.1(6) . . ?
C12 C11 H11A 110.7 . . ?
N15 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
N15 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C11 C12 C13 102.6(6) . . ?
C11 C12 H12A 111.2 . . ?
C13 C12 H12A 111.2 . . ?
C11 C12 H12B 111.2 . . ?
C13 C12 H12B 111.2 . . ?
H12A C12 H12B 109.2 . . ?
C14 C13 C12 106.4(6) . . ?
C14 C13 H13A 110.4 . . ?
C12 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
C12 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
N15 C14 C13 104.6(6) . . ?
N15 C14 H14A 110.8 . . ?
C13 C14 H14A 110.8 . . ?
N15 C14 H14B 110.8 . . ?
C13 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
C11 N15 C14 108.3(5) . . ?
C11 N15 H15A 110.0 . . ?
C14 N15 H15A 110.0 . . ?
C11 N15 H15B 110.0 . . ?
C14 N15 H15B 110.0 . . ?
H15A N15 H15B 108.4 . . ?
C17 N16 C20 104.8(5) . . ?
C17 N16 H16A 110.8 . . ?
C20 N16 H16A 110.8 . . ?
C17 N16 H16B 110.8 . . ?
C20 N16 H16B 110.8 . . ?
H16A N16 H16B 108.9 . . ?
N16 C17 C18 104.4(5) . . ?
N16 C17 H17A 110.9 . . ?
C18 C17 H17A 110.9 . . ?
N16 C17 H17B 110.9 . . ?
C18 C17 H17B 110.9 . . ?
H17A C17 H17B 108.9 . . ?
C17 C18 C19 106.5(5) . . ?
C17 C18 H18A 110.4 . . ?
C19 C18 H18A 110.4 . . ?
C17 C18 H18B 110.4 . . ?
C19 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
C18 C19 C20 105.1(6) . . ?
C18 C19 H19A 110.7 . . ?
C20 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
C20 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?
N16 C20 C19 103.3(5) . . ?
N16 C20 H20A 111.1 . . ?
C19 C20 H20A 111.1 . . ?
N16 C20 H20B 111.1 . . ?
C19 C20 H20B 111.1 . . ?
H20A C20 H20B 109.1 . . ?

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
N5 H5A Cl31 0.89 2.24 3.114(5) 167.0 1_455 yes
N5 H5B Cl20 0.89 2.55 3.315(6) 144.8 1_455 yes
N5 H5B Cl41 0.89 2.72 3.280(5) 121.9 1_455 yes
N8 H8A Cl30 0.89 2.34 3.202(6) 162.5 1_545 yes
N8 H8B Cl31 0.89 2.28 3.137(5) 160.8 1_455 yes
N15 H15A Cl30 0.89 2.46 3.237(5) 146.7 1_645 yes
N15 H15A Cl40 0.89 2.94 3.489(5) 121.5 1_645 yes
N15 H15B Cl41 0.89 2.45 3.276(5) 155.0 1_545 yes
N16 H16A Cl40 0.89 2.30 3.187(6) 177.6 . yes
N16 H16B Cl12 0.89 2.80 3.447(5) 130.6 . yes
N16 H16B Cl41 0.89 2.59 3.248(5) 131.4 . yes

_refine_diff_density_max         0.495
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.056


_exptl_crystal_preparation       ferroelectric
####################################################################### 
# 
# 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_pnma
_database_code_depnum_ccdc_archive 'CCDC 1918926'
loop_
_audit_author_name
_audit_author_address
'Anna Gagor'
;ILT SR PAS Wroclaw Poland
Poland
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2019-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H20 Cl5 N2 Sb'
_chemical_formula_weight         443.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P m n b'
_space_group_name_Hall           ?

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

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

_cell_length_a                   8.5385(5)
_cell_length_b                   11.0894(4)
_cell_length_c                   17.9031(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1695.19(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    269.96(16)
_cell_measurement_reflns_used    4574
_cell_measurement_theta_min      3.2150
_cell_measurement_theta_max      22.2050

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.396
_exptl_absorpt_correction_T_min  0.86914
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.918
_oxdiff_exptl_absorpt_empirical_full_max 1.110
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      269.96(16)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            14590
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.643
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_full        25.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1720
_reflns_number_gt                1186
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1603P)²+2.5609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1720
_refine_ls_number_parameters     103
_refine_ls_number_restraints     94
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0747
_refine_ls_wR_factor_ref         0.2702
_refine_ls_wR_factor_gt          0.2412
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.004

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.250000 0.65479(9) -0.56825(5) 0.1052(6) Uani 1 2 d S T P . .
Cl1 Cl 0.0502(5) 0.7746(4) -0.6275(3) 0.1649(15) Uani 1 1 d . . . . .
Cl2 Cl 0.250000 0.5111(5) -0.6754(3) 0.165(2) Uani 1 2 d S T P . .
Cl3 Cl 0.250000 0.8129(10) -0.4455(5) 0.274(6) Uani 1 2 d S T P . .
Cl4 Cl 0.000000 0.500000 -0.500000 0.186(2) Uani 1 2 d S . P . .
C1 C 0.250000 0.5157(17) -0.2254(12) 0.292(9) Uani 1 2 d DS TU P . .
H11 H 0.158129 0.509106 -0.193741 0.351 Uiso 0.5 1 calc R U P . .
H12 H 0.341871 0.509107 -0.193741 0.351 Uiso 0.5 1 calc R U P . .
C2 C 0.250000 0.6324(19) -0.2619(10) 0.296(9) Uani 1 2 d DS TU P . .
H21 H 0.342128 0.677824 -0.247272 0.355 Uiso 0.5 1 calc R U P . .
H22 H 0.157872 0.677823 -0.247272 0.355 Uiso 0.5 1 calc R U P . .
C3 C 0.250000 0.6132(17) -0.3420(10) 0.297(9) Uani 1 2 d DS TU P . .
H31 H 0.157494 0.648070 -0.364852 0.357 Uiso 0.5 1 calc R U P . .
H32 H 0.342506 0.648071 -0.364852 0.357 Uiso 0.5 1 calc R U P . .
N4 N 0.250000 0.4830(17) -0.3491(11) 0.294(9) Uani 1 2 d DS TU P . .
H41 H 0.334077 0.461114 -0.375199 0.353 Uiso 0.5 1 calc R U P . .
H42 H 0.165923 0.461114 -0.375199 0.353 Uiso 0.5 1 calc R U P . .
C5 C 0.250000 0.4177(19) -0.2790(10) 0.294(9) Uani 1 2 d DS TU P . .
H51 H 0.342663 0.367753 -0.273916 0.352 Uiso 0.5 1 calc R U P . .
H52 H 0.157337 0.367753 -0.273916 0.352 Uiso 0.5 1 calc R U P . .
C11 C -0.250000 0.801(2) -0.3553(8) 0.222(8) Uani 1 2 d DS TU P . .
H111 H -0.318692 0.739230 -0.335077 0.267 Uiso 0.5 1 calc R U P . .
H112 H -0.169821 0.818601 -0.318501 0.267 Uiso 0.5 1 calc R U P . .
N21 N -0.179(3) 0.759(2) -0.4241(9) 0.221(8) Uani 0.5 1 d D U P . .
H211 H -0.075843 0.771877 -0.423128 0.266 Uiso 0.5 1 calc R U P . .
H212 H -0.195396 0.680328 -0.429955 0.266 Uiso 0.5 1 calc R U P . .
C31 C -0.250000 0.8260(19) -0.4848(7) 0.214(8) Uani 1 2 d DS TU P . .
H311 H -0.169428 0.861999 -0.515779 0.257 Uiso 0.5 1 calc R U P . .
H312 H -0.312166 0.772307 -0.515625 0.257 Uiso 0.5 1 calc R U P . .
C41 C -0.349(4) 0.919(2) -0.4532(9) 0.212(8) Uani 0.5 1 d D U P . .
H411 H -0.313031 0.998246 -0.469086 0.255 Uiso 0.5 1 calc R U P . .
H412 H -0.456221 0.908750 -0.469475 0.255 Uiso 0.5 1 calc R U P . .
C51 C -0.339(3) 0.909(2) -0.3726(9) 0.216(8) Uani 0.5 1 d D U P . .
H511 H -0.286818 0.979058 -0.351822 0.259 Uiso 0.5 1 calc R U P . .
H512 H -0.442771 0.903440 -0.351151 0.259 Uiso 0.5 1 calc R U 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
Sb1 Cl1 2.408(3) . ?
Sb1 Cl1 2.408(3) 7_655 ?
Sb1 Cl2 2.494(5) . ?
Sb1 Cl3 2.811(7) . ?
Sb1 Cl4 2.9994(6) . ?
Sb1 Cl4 2.9994(6) 3_564 ?
Cl1 H511 21.84(2) 1_464 ?
Cl4 H412 26.456(14) 1_464 ?
Cl4 H412 26.456(15) 5_655 ?
C1 C2 1.4499(10) . ?
C1 C5 1.4499(10) . ?
C1 H11 0.9700 . ?
C1 H12 0.9700 . ?
C2 C3 1.4500(10) . ?
C2 H21 0.9700 . ?
C2 H22 0.9700 . ?
C2 H21 10.35(3) 5_665 ?
C2 H21 10.35(3) 3_465 ?
C3 N4 1.4499(10) . ?
C3 H31 0.9700 . ?
C3 H32 0.9700 . ?
N4 C5 1.4499(10) . ?
N4 H41 0.8900 . ?
N4 H42 0.8900 . ?
C5 H51 0.9700 . ?
C5 H52 0.9700 . ?
C11 C51 1.4501(10) . ?
C11 N21 1.4504(10) . ?
C11 H111 0.9700 . ?
C11 H112 0.9700 . ?
N21 C31 1.4502(10) . ?
N21 H211 0.8900 . ?
N21 H212 0.8900 . ?
N21 H311 24.560(2) 1_464 ?
C31 C41 1.4501(10) . ?
C31 H311 0.9700 . ?
C31 H312 0.9700 . ?
C31 H311 23.1155 1_464 ?
C31 H311 23.1155 7_664 ?
C41 C51 1.4501(10) . ?
C41 H411 0.9700 . ?
C41 H412 0.9700 . ?
C51 H511 0.9700 . ?
C51 H512 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Sb1 Cl1 90.2(2) . 7_655 ?
Cl1 Sb1 Cl2 90.79(16) . . ?
Cl1 Sb1 Cl2 90.79(16) 7_655 . ?
Cl1 Sb1 Cl3 90.0(2) . . ?
Cl1 Sb1 Cl3 90.0(2) 7_655 . ?
Cl2 Sb1 Cl3 178.9(3) . . ?
Cl1 Sb1 Cl4 89.49(11) . . ?
Cl1 Sb1 Cl4 177.77(13) 7_655 . ?
Cl2 Sb1 Cl4 87.00(10) . . ?
Cl3 Sb1 Cl4 92.21(19) . . ?
Cl1 Sb1 Cl4 177.77(13) . 3_564 ?
Cl1 Sb1 Cl4 89.49(11) 7_655 3_564 ?
Cl2 Sb1 Cl4 87.00(10) . 3_564 ?
Cl3 Sb1 Cl4 92.21(19) . 3_564 ?
Cl4 Sb1 Cl4 90.75(2) . 3_564 ?


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
N4 H41 Cl4 0.89 2.68 3.448(15) 145.0 3_564 yes
N4 H42 Cl4 0.89 2.68 3.448(15) 145.0 . yes
N21 H211 Cl3 0.89 2.85 3.73(3) 170.8 . yes
N21 H212 Cl4 0.89 2.89 3.525(15) 129.6 . yes
N21 H212 Cl2 0.89 2.88 3.54(3) 132.2 5_564 yes

_refine_diff_density_max         0.788
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_240K
_database_code_depnum_ccdc_archive 'CCDC 1918927'
loop_
_audit_author_name
_audit_author_address
'Anna Gagor'
;ILT SR PAS Wroclaw Poland
Poland
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2019-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H20 Cl5 N2 Sb'
_chemical_formula_weight         443.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

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

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

_cell_length_a                   8.5703(4)
_cell_length_b                   10.9382(6)
_cell_length_c                   17.7953(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.805(5)
_cell_angle_gamma                90
_cell_volume                     1668.03(15)
_cell_formula_units_Z            6
_cell_measurement_temperature    239.94(19)
_cell_measurement_reflns_used    5792
_cell_measurement_theta_min      3.0420
_cell_measurement_theta_max      26.4920

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.435
_exptl_absorpt_correction_T_min  0.39780
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.532
_oxdiff_exptl_absorpt_empirical_full_max 2.362
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      239.94(19)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            6293
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.624
_diffrn_reflns_theta_max         25.675
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6293
_reflns_number_gt                5483
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;


_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1390P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.43(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6293
_refine_ls_number_parameters     290
_refine_ls_number_restraints     182
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1789
_refine_ls_wR_factor_gt          0.1735
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.104
_refine_ls_shift/su_mean         0.009

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.25633(18) 0.43816(11) 0.06781(8) 0.0440(3) Uani 1 1 d . . . . .
Sb2 Sb 0.74395(17) 0.12465(11) -0.06745(8) 0.0430(3) Uani 1 1 d . . . . .
Cl10 Cl 0.0862(12) 0.5762(10) 0.1305(7) 0.098(3) Uani 1 1 d . . . . .
Cl11 Cl 0.4802(9) 0.5220(9) 0.1324(5) 0.076(2) Uani 1 1 d . . . . .
Cl12 Cl 0.5625(13) -0.0158(11) -0.1235(7) 0.089(3) Uani 1 1 d . . . . .
Cl13 Cl 0.9651(11) 0.0084(7) -0.1150(6) 0.074(3) Uani 1 1 d . . . . .
Cl20 Cl 0.2301(18) 0.2881(10) 0.1695(5) 0.102(3) Uani 1 1 d . . . . .
Cl21 Cl 0.7450(18) 0.2529(7) -0.1791(3) 0.0822(19) Uani 1 1 d . . . . .
Cl30 Cl 0.3222(11) 0.6193(7) -0.0410(5) 0.0709(19) Uani 1 1 d . . . . .
Cl31 Cl 0.7203(8) -0.0325(6) 0.0695(5) 0.0644(17) Uani 1 1 d . . . . .
Cl40 Cl 0.9681(9) 0.3176(7) -0.0086(4) 0.0635(17) Uani 1 1 d . . . . .
Cl41 Cl 0.4795(8) 0.2756(7) -0.0191(5) 0.0627(18) Uani 1 1 d . . . . .
C1 C 0.761(5) 0.623(3) -0.0049(16) 0.087(6) Uani 1 1 d D U . . .
H1A H 0.814432 0.581932 0.036608 0.105 Uiso 1 1 calc R U . . .
H1B H 0.681429 0.675746 0.015108 0.105 Uiso 1 1 calc R U . . .
C2 C 0.872(5) 0.692(3) -0.0494(16) 0.092(6) Uani 1 1 d D U . . .
H2A H 0.977964 0.669708 -0.036244 0.111 Uiso 1 1 calc R U . . .
H2B H 0.858534 0.779165 -0.040875 0.111 Uiso 1 1 calc R U . . .
C3 C 0.837(5) 0.662(4) -0.1274(18) 0.098(6) Uani 1 1 d D U . . .
H3A H 0.805574 0.735207 -0.154190 0.117 Uiso 1 1 calc R U . . .
H3B H 0.930199 0.630168 -0.150715 0.117 Uiso 1 1 calc R U . . .
C4 C 0.713(4) 0.572(3) -0.1334(15) 0.091(6) Uani 1 1 d D U . . .
H4A H 0.618462 0.607218 -0.153957 0.109 Uiso 1 1 calc R U . . .
H4B H 0.744333 0.503252 -0.164565 0.109 Uiso 1 1 calc R U . . .
N5 N 0.693(3) 0.534(3) -0.0559(14) 0.087(6) Uani 1 1 d D U . . .
H5A H 0.591696 0.525952 -0.046632 0.104 Uiso 1 1 calc R U . . .
H5B H 0.738081 0.461315 -0.048600 0.104 Uiso 1 1 calc R U . . .
N6 N 1.210(3) 0.2563(17) -0.1454(12) 0.073(5) Uani 1 1 d D U . . .
H6A H 1.123342 0.234467 -0.121567 0.087 Uiso 1 1 calc R U . . .
H6B H 1.289994 0.252950 -0.113221 0.087 Uiso 1 1 calc R U . . .
C7 C 1.194(4) 0.378(2) -0.1769(17) 0.074(5) Uani 1 1 d D U . . .
H7A H 1.217083 0.439299 -0.139181 0.089 Uiso 1 1 calc R U . . .
H7B H 1.087991 0.390731 -0.195641 0.089 Uiso 1 1 calc R U . . .
C8 C 1.304(4) 0.385(2) -0.2380(17) 0.075(5) Uani 1 1 d D U . . .
H8A H 1.272100 0.443837 -0.275786 0.090 Uiso 1 1 calc R U . . .
H8B H 1.408531 0.404152 -0.219941 0.090 Uiso 1 1 calc R U . . .
C9 C 1.294(4) 0.260(2) -0.2662(17) 0.081(5) Uani 1 1 d D U . . .
H9A H 1.225170 0.258487 -0.309864 0.098 Uiso 1 1 calc R U . . .
H9B H 1.396564 0.233721 -0.281662 0.098 Uiso 1 1 calc R U . . .
C10 C 1.236(6) 0.178(2) -0.2098(13) 0.080(5) Uani 1 1 d D U . . .
H10A H 1.312063 0.114705 -0.197866 0.096 Uiso 1 1 calc R U . . .
H10B H 1.139591 0.139103 -0.226535 0.096 Uiso 1 1 calc R U . . .
C11 C 1.252(5) -0.188(4) -0.2211(17) 0.109(7) Uani 1 1 d D U . . .
H11A H 1.280373 -0.220565 -0.172101 0.130 Uiso 1 1 calc R U . . .
H11B H 1.198429 -0.110814 -0.214255 0.130 Uiso 1 1 calc R U . . .
C12 C 1.391(5) -0.170(5) -0.2658(15) 0.103(7) Uani 1 1 d D U . . .
H12A H 1.424685 -0.085568 -0.262322 0.124 Uiso 1 1 calc R U . . .
H12B H 1.474797 -0.221528 -0.246686 0.124 Uiso 1 1 calc R U . . .
N13 N 1.357(4) -0.201(3) -0.3436(14) 0.099(6) Uani 1 1 d D U . . .
H13A H 1.349739 -0.134117 -0.372012 0.119 Uiso 1 1 calc R U . . .
H13B H 1.429421 -0.250132 -0.362194 0.119 Uiso 1 1 calc R U . . .
C14 C 1.208(4) -0.262(5) -0.3389(16) 0.109(7) Uani 1 1 d D U . . .
H14A H 1.217195 -0.343522 -0.360356 0.131 Uiso 1 1 calc R U . . .
H14B H 1.131142 -0.217583 -0.368342 0.131 Uiso 1 1 calc R U . . .
C15 C 1.155(5) -0.273(5) -0.2618(16) 0.113(7) Uani 1 1 d D U . . .
H15A H 1.045503 -0.250369 -0.258144 0.136 Uiso 1 1 calc R U . . .
H15B H 1.168574 -0.355305 -0.242916 0.136 Uiso 1 1 calc R U . . .
C16 C 0.846(4) 0.141(3) -0.3626(15) 0.078(5) Uani 1 1 d D U . . .
H16A H 0.820741 0.224558 -0.348303 0.094 Uiso 1 1 calc R U . . .
H16B H 0.935774 0.114841 -0.333363 0.094 Uiso 1 1 calc R U . . .
N17 N 0.879(3) 0.136(2) -0.4421(13) 0.075(5) Uani 1 1 d D U . . .
H17A H 0.875331 0.210404 -0.461996 0.090 Uiso 1 1 calc R U . . .
H17B H 0.974629 0.105738 -0.448840 0.090 Uiso 1 1 calc R U . . .
C18 C 0.764(4) 0.058(3) -0.4782(15) 0.084(5) Uani 1 1 d D U . . .
H18A H 0.704707 0.103471 -0.515447 0.101 Uiso 1 1 calc R U . . .
H18B H 0.815125 -0.010048 -0.503216 0.101 Uiso 1 1 calc R U . . .
C19 C 0.662(4) 0.012(4) -0.4203(15) 0.091(6) Uani 1 1 d D U . . .
H19A H 0.665292 -0.076329 -0.418983 0.110 Uiso 1 1 calc R U . . .
H19B H 0.555430 0.037376 -0.430932 0.110 Uiso 1 1 calc R U . . .
C20 C 0.713(4) 0.061(3) -0.3481(16) 0.088(6) Uani 1 1 d D U . . .
H20A H 0.744081 -0.004363 -0.314511 0.105 Uiso 1 1 calc R U . . .
H20B H 0.629501 0.107089 -0.325129 0.105 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Cl10 2.387(8) . ?
Sb1 Cl11 2.405(8) . ?
Sb1 Cl20 2.456(8) . ?
Sb1 Cl40 2.686(8) ? ?
Sb1 Cl30 2.833(8) . ?
Sb1 Cl41 3.049(7) . ?
Sb2 Cl12 2.393(9) . ?
Sb2 Cl21 2.432(6) . ?
Sb2 Cl13 2.443(8) . ?
Sb2 Cl41 2.942(7) . ?
Sb2 Cl40 3.031(7) . ?
C1 N5 1.447(14) . ?
C1 C2 1.457(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.454(14) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.449(14) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N5 1.452(14) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
N6 C7 1.448(14) . ?
N6 C10 1.453(14) . ?
N6 H6A 0.8900 . ?
N6 H6B 0.8900 . ?
C7 C8 1.455(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.450(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.446(14) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C15 1.439(14) . ?
C11 C12 1.451(14) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N13 1.452(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
N13 C14 1.444(14) . ?
N13 H13A 0.8900 . ?
N13 H13B 0.8900 . ?
C14 C15 1.457(14) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N17 1.450(14) . ?
C16 C20 1.458(14) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
N17 C18 1.449(14) . ?
N17 H17A 0.8900 . ?
N17 H17B 0.8900 . ?
C18 C19 1.450(14) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.453(14) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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
Cl10 Sb1 Cl11 91.4(4) . . ?
Cl10 Sb1 Cl20 90.9(5) . . ?
Cl11 Sb1 Cl20 89.0(4) . . ?
Cl10 Sb1 Cl40 96.3(3) . ? ?
Cl11 Sb1 Cl40 172.0(3) . ? ?
Cl20 Sb1 Cl40 88.4(3) . ? ?
Cl10 Sb1 Cl30 90.3(4) . . ?
Cl11 Sb1 Cl30 84.0(3) . . ?
Cl20 Sb1 Cl30 172.9(4) . . ?
Cl40 Sb1 Cl30 98.4(2) ? . ?
Cl10 Sb1 Cl41 176.2(4) . . ?
Cl11 Sb1 Cl41 87.9(3) . . ?
Cl20 Sb1 Cl41 92.8(4) . . ?
Cl40 Sb1 Cl41 84.7(2) ? . ?
Cl30 Sb1 Cl41 85.9(2) . . ?
Cl12 Sb2 Cl21 92.3(4) . . ?
Cl12 Sb2 Cl13 91.4(4) . . ?
Cl21 Sb2 Cl13 90.3(4) . . ?
Cl12 Sb2 Cl41 89.1(3) . . ?
Cl21 Sb2 Cl41 85.8(3) . . ?
Cl13 Sb2 Cl41 176.1(3) . . ?
Cl12 Sb2 Cl40 174.8(4) . . ?
Cl21 Sb2 Cl40 82.6(3) . . ?
Cl13 Sb2 Cl40 89.5(3) . . ?
Cl41 Sb2 Cl40 89.7(2) . . ?
Sb2 Cl41 Sb1 165.2(3) . . ?
N5 C1 C2 106(2) . . ?
N5 C1 H1A 110.6 . . ?
C2 C1 H1A 110.6 . . ?
N5 C1 H1B 110.6 . . ?
C2 C1 H1B 110.6 . . ?
H1A C1 H1B 108.7 . . ?
C1 C2 C3 106(3) . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C4 C3 C2 111(3) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
N5 C4 C3 103(3) . . ?
N5 C4 H4A 111.2 . . ?
C3 C4 H4A 111.1 . . ?
N5 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C1 N5 C4 111(2) . . ?
C1 N5 H5A 109.6 . . ?
C4 N5 H5A 109.5 . . ?
C1 N5 H5B 109.5 . . ?
C4 N5 H5B 109.5 . . ?
H5A N5 H5B 108.1 . . ?
C7 N6 C10 105(2) . . ?
C7 N6 H6A 110.8 . . ?
C10 N6 H6A 110.8 . . ?
C7 N6 H6B 110.8 . . ?
C10 N6 H6B 110.9 . . ?
H6A N6 H6B 108.9 . . ?
N6 C7 C8 106(2) . . ?
N6 C7 H7A 110.5 . . ?
C8 C7 H7A 110.5 . . ?
N6 C7 H7B 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C9 C8 C7 100(2) . . ?
C9 C8 H8A 111.8 . . ?
C7 C8 H8A 111.8 . . ?
C9 C8 H8B 111.8 . . ?
C7 C8 H8B 111.8 . . ?
H8A C8 H8B 109.5 . . ?
C10 C9 C8 112(2) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 N6 104(2) . . ?
C9 C10 H10A 111.0 . . ?
N6 C10 H10A 111.0 . . ?
C9 C10 H10B 111.1 . . ?
N6 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
C15 C11 C12 107(3) . . ?
C15 C11 H11A 110.4 . . ?
C12 C11 H11A 110.5 . . ?
C15 C11 H11B 110.4 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
N13 C12 C11 110(3) . . ?
N13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
N13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 N13 C12 103(3) . . ?
C14 N13 H13A 111.1 . . ?
C12 N13 H13A 111.2 . . ?
C14 N13 H13B 111.4 . . ?
C12 N13 H13B 111.3 . . ?
H13A N13 H13B 109.2 . . ?
N13 C14 C15 112(3) . . ?
N13 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C11 C15 C14 104(3) . . ?
C11 C15 H15A 111.1 . . ?
C14 C15 H15A 110.9 . . ?
C11 C15 H15B 111.0 . . ?
C14 C15 H15B 111.2 . . ?
H15A C15 H15B 109.0 . . ?
N17 C16 C20 108(2) . . ?
N17 C16 H16A 110.0 . . ?
C20 C16 H16A 110.1 . . ?
N17 C16 H16B 110.0 . . ?
C20 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
C18 N17 C16 108(2) . . ?
C18 N17 H17A 110.0 . . ?
C16 N17 H17A 110.1 . . ?
C18 N17 H17B 110.1 . . ?
C16 N17 H17B 110.0 . . ?
H17A N17 H17B 108.4 . . ?
C19 C18 N17 107(2) . . ?
C19 C18 H18A 110.2 . . ?
N17 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
N17 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
C18 C19 C20 109(2) . . ?
C18 C19 H19A 109.9 . . ?
C20 C19 H19A 109.9 . . ?
C18 C19 H19B 109.9 . . ?
C20 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
C19 C20 C16 107(2) . . ?
C19 C20 H20A 110.3 . . ?
C16 C20 H20A 110.3 . . ?
C19 C20 H20B 110.3 . . ?
C16 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?

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
#N5 H5A Cl41  0.89 2.94 3.43(3) 116.2 . yes
N5 H5A Cl30 0.89 2.53 3.33(3) 149.6 . yes
N5 H5B Cl40 0.89 2.61 3.44(3) 154.2 . yes
N6 H6A Cl13 0.89 2.82 3.47(2) 131.1 . yes
N6 H6A Cl40 0.89 2.59 3.29(2) 135.5 . yes
N6 H6B Cl41 0.89 2.33 3.21(3) 169.5 1_655 yes
N13 H13A Cl31 0.89 2.37 3.20(4) 155.7 2_554 yes
N13 H13B Cl20 0.89 2.66 3.34(4) 134.1 2_654 yes
N13 H13B Cl40 0.89 2.73 3.35(3) 127.9 2_554 yes
N17 H17A Cl30 0.89 2.37 3.24(3) 163.9 2_564 yes
N17 H17B Cl31 0.89 2.27 3.14(3) 164.0 2_554 yes

_refine_diff_density_max         1.694
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.156


_exptl_crystal_preparation       ferroelectric
####################################################################### 
# 
# 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_Pmn21-trans
_database_code_depnum_ccdc_archive 'CCDC 1918925'
loop_
_audit_author_name
_audit_author_address
'Anna Gagor'
;ILT SR PAS Wroclaw Poland
Poland
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2019-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H20 Cl5 N2 Sb'
_chemical_formula_weight         443.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_H-M_alt        'P m n 21'
_space_group_name_Hall           'P 2ac -2'

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

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

_cell_length_a                   8.5385(6)
_cell_length_b                   11.0894(5)
_cell_length_c                   17.9031(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1695.19(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    254.99(10)
_cell_measurement_reflns_used    3401
_cell_measurement_theta_min      3.0000
_cell_measurement_theta_max      24.8040

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.396
_exptl_absorpt_correction_T_min  0.72787
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.876
_oxdiff_exptl_absorpt_empirical_full_max 1.338
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      254.99(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            12609
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.643
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_full        25.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.795
_diffrn_reflns_point_group_measured_fraction_full 0.795
_reflns_number_total             2743
_reflns_number_gt                2240
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.541
_reflns_Friedel_fraction_max     0.578
_reflns_Friedel_fraction_full    0.578

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1373P)²+1.1179P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2743
_refine_ls_number_parameters     153
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1974
_refine_ls_wR_factor_gt          0.1814
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.000000 -0.42274(14) 0.4930(9) 0.0901(5) Uani 1 2 d S T P . .
Sb2 Sb -0.500000 -0.11229(14) 0.3563(9) 0.0889(5) Uani 1 2 d S T P . .
Cl10 Cl 0.1993(8) -0.5366(6) 0.5562(10) 0.154(2) Uani 1 1 d . . . . .
Cl12 Cl -0.7004(7) 0.0115(6) 0.3006(9) 0.141(2) Uani 1 1 d . . . . .
Cl21 Cl -0.500000 -0.2464(8) 0.2462(10) 0.137(3) Uani 1 2 d S T P . .
Cl20 Cl 0.000000 -0.2700(9) 0.5962(10) 0.150(3) Uani 1 2 d S T P . .
Cl30 Cl 0.000000 -0.6030(13) 0.3851(11) 0.236(8) Uani 1 2 d S T P . .
Cl31 Cl 0.500000 1.0392(9) -0.5102(11) 0.190(5) Uani 1 2 d S T P . .
Cl40 Cl -0.2512(8) -0.2731(7) 0.4160(9) 0.155(2) Uani 1 1 d . . . . .
N10 N 0.047(2) -0.246(2) 0.2781(16) 0.082(6) Uiso 0.5 1 d D . P . .
C20 C -0.034(8) -0.178(5) 0.220(3) 0.19(3) Uiso 0.5 1 d D . P . .
C30 C 0.00(3) -0.244(4) 0.153(3) 0.173(16) Uiso 1 2 d D . P . .
C40 C -0.03(2) -0.360(8) 0.186(6) 0.33(6) Uiso 0.5 1 d D . P . .
C50 C -0.051(10) -0.351(6) 0.266(5) 0.26(4) Uiso 0.5 1 d D . P . .
C21 C 0.542(4) 0.6946(19) -0.4022(12) 0.150(7) Uiso 0.5 1 d D . P . .
C31 C 0.573(4) 0.699(2) -0.3226(11) 0.150(7) Uiso 0.5 1 d D . P . .
C41 C 0.500000 0.813(2) -0.3050(11) 0.150(7) Uiso 1 2 d DS . P . .
C51 C 0.636(2) 0.854(3) -0.3459(12) 0.150(7) Uiso 0.5 1 d D . P . .
N11 N 0.591(3) 0.816(2) -0.4203(10) 0.150(7) Uiso 0.5 1 d D . P . .
N13 N 0.432(5) 0.479(3) 0.3685(14) 0.200(11) Uiso 0.5 1 d D . P . .
C23 C 0.500000 0.441(3) 0.2980(18) 0.200(11) Uiso 1 2 d DS . P . .
C33 C 0.597(6) 0.334(3) 0.2934(15) 0.200(11) Uiso 0.5 1 d D . P . .
C43 C 0.596(6) 0.311(4) 0.3731(14) 0.200(11) Uiso 0.5 1 d D . P . .
C53 C 0.500000 0.390(3) 0.4184(18) 0.200(11) Uiso 1 2 d DS . P . .
N12 N 0.096(2) 0.027(3) 0.5055(10) 0.161(8) Uani 0.5 1 d D U P . .
C22 C 0.000000 0.085(3) 0.4490(8) 0.154(8) Uani 1 2 d DS TU P . .
C32 C -0.1328(18) 0.125(3) 0.4927(11) 0.153(8) Uani 0.5 1 d D U P . .
C42 C -0.053(3) 0.164(2) 0.5600(12) 0.156(8) Uani 0.5 1 d D U P . .
C52 C 0.000000 0.042(2) 0.5717(10) 0.158(8) Uani 1 2 d DS TU 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
Sb1 Cl10 2.402(6) 4 ?
Sb1 Cl10 2.402(6) . ?
Sb1 Cl20 2.506(9) . ?
Sb1 Cl30 2.780(11) . ?
Sb1 Cl40 3.043(6) . ?
Sb2 Cl12 2.409(5) 4_455 ?
Sb2 Cl12 2.409(5) . ?
Sb2 Cl21 2.469(7) . ?
Sb2 Cl40 2.972(6) . ?
N10 C50 1.450(13) . ?
N10 C20 1.460(13) . ?
C20 C30 1.449(13) . ?
C20 C30 1.44(11) 4 ?
C30 C40 1.451(13) . ?
C30 C40 1.44(11) 4 ?
C40 C50 1.453(13) . ?
C21 N11 1.4500(13) . ?
C21 C31 1.4501(13) . ?
C31 C41 1.4500(13) . ?
C41 C51 1.4500(13) . ?
C41 C51 1.4500(13) 4_655 ?
C51 N11 1.4501(13) . ?
N13 C53 1.4500(13) . ?
N13 C23 1.4501(13) . ?
C23 C33 1.4499(13) 4_655 ?
C23 C33 1.4500(13) . ?
C33 C43 1.4500(13) . ?
C43 C53 1.4500(13) . ?
N12 C22 1.4495(13) . ?
N12 C52 1.4496(13) . ?
C22 C32 1.4494(13) 4 ?
C22 C32 1.4494(13) . ?
C32 C42 1.4497(13) . ?
C42 C52 1.4498(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl10 Sb1 Cl10 90.2(4) 4 . ?
Cl10 Sb1 Cl20 90.5(3) 4 . ?
Cl10 Sb1 Cl20 90.5(3) . . ?
Cl10 Sb1 Cl30 87.1(3) 4 . ?
Cl10 Sb1 Cl30 87.1(3) . . ?
Cl20 Sb1 Cl30 176.5(4) . . ?
Cl10 Sb1 Cl40 90.0(2) 4 . ?
Cl10 Sb1 Cl40 178.5(2) . . ?
Cl20 Sb1 Cl40 88.0(2) . . ?
Cl30 Sb1 Cl40 94.4(3) . . ?
Cl12 Sb2 Cl12 90.5(3) 4_455 . ?
Cl12 Sb2 Cl21 90.7(2) 4_455 . ?
Cl12 Sb2 Cl21 90.7(2) . . ?
Cl12 Sb2 Cl40 89.0(2) 4_455 . ?
Cl12 Sb2 Cl40 176.4(2) . . ?
Cl21 Sb2 Cl40 85.7(2) . . ?
Cl12 Sb2 Cl31 25.19(17) 4_455 . ?
Cl12 Sb2 Cl31 69.55(16) . . ?
Cl21 Sb2 Cl31 77.58(19) . . ?
Cl40 Sb2 Cl31 109.08(16) . . ?
Sb2 Cl40 Sb1 173.7(3) . . ?


_refine_diff_density_max         0.920
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.129


_exptl_crystal_preparation       ferroelectric
