# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_77-300k_auto
_database_code_depnum_ccdc_archive 'CCDC 2210039'
loop_
_audit_author_name
_audit_author_address
'Xinxin Hu'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2022-12-22 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;
_audit_creation_date             2022-12-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br3 Sn0.5), 2(C5 H12 N)'
_chemical_formula_sum            'C10 H24 Br6 N2 Sn'
_chemical_formula_weight         770.46
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn 0.1164 4.3256 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           32
_space_group_name_H-M_alt        'P b a 2'
_space_group_name_Hall           'P 2 -2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'

_cell_length_a                   15.5317(4)
_cell_length_b                   13.8647(3)
_cell_length_c                   10.0184(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2157.39(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7423
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      59.8530
_cell_measurement_theta_min      2.4570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    15.044
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15344
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.129
_diffrn_reflns_theta_min         3.715
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  ROM
_diffrn_measurement_method       ?
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   ?
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3535
_reflns_number_total             4550
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.066
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         4550
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.084
_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)+(0.0992P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1583
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.49(4)
 0.51(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C14-C13
 1.45 with sigma of 0.02
 C12-C11
 1.5 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C16)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Ternary CH refined with riding coordinates:
 N9(H9), N10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C18(H18A,H18B), C11(H11A,H11B), C19(H19A,
 H19B), C17(H17A,H17B), C12(H12A,H12B), C13(H13A,H13B)
5.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.500000 0.500000 0.7488(3) 0.0427(2) Uani 1 2 d S T P . .
Sn2 Sn 0.500000 0.000000 0.2487(4) 0.0490(2) Uani 1 2 d S T P . .
Br3 Br 0.50337(13) 0.63364(17) 0.93034(18) 0.0630(7) Uani 1 1 d . . . . .
Br4 Br 0.66691(6) 0.49986(6) 0.7463(5) 0.0616(3) Uani 1 1 d . . . . .
Br8 Br 0.60575(16) 0.06093(19) 0.4333(2) 0.0774(7) Uani 1 1 d . . . . .
Br5 Br 0.49578(14) 0.36743(17) 0.5667(2) 0.0664(8) Uani 1 1 d . . . . .
Br7 Br 0.42430(8) 0.16586(8) 0.2483(5) 0.0890(4) Uani 1 1 d . . . . .
Br6 Br 0.39444(18) -0.0612(2) 0.0669(3) 0.0857(8) Uani 1 1 d . . . . .
N9 N 0.3758(6) 0.2009(7) 0.753(2) 0.081(3) Uani 1 1 d . . . . .
H9 H 0.403605 0.264294 0.756995 0.098 Uiso 1 1 calc R U . . .
N10 N 0.2050(6) 0.0061(6) 0.249(3) 0.071(2) Uani 1 1 d . . . . .
H10 H 0.267301 0.006292 0.233330 0.086 Uiso 1 1 calc R U . . .
C14 C 0.3268(13) 0.1893(16) 0.870(2) 0.076(5) Uani 1 1 d D U . . .
H14A H 0.357616 0.212110 0.947680 0.092 Uiso 1 1 calc R U . . .
H14B H 0.310134 0.122599 0.882808 0.092 Uiso 1 1 calc R U . . .
C16 C 0.166(2) 0.055(2) 0.145(3) 0.111(9) Uani 1 1 d . U . . .
H16A H 0.104089 0.042659 0.145503 0.134 Uiso 1 1 calc R U . . .
H16B H 0.189098 0.034427 0.060277 0.134 Uiso 1 1 calc R U . . .
C20 C 0.1731(10) -0.0969(10) 0.240(5) 0.119(7) Uani 1 1 d . . . . .
H20A H 0.111344 -0.097364 0.241327 0.179 Uiso 1 1 calc R U . . .
H20B H 0.194468 -0.132863 0.315253 0.179 Uiso 1 1 calc R U . . .
H20C H 0.193418 -0.125667 0.159100 0.179 Uiso 1 1 calc R U . . .
C18 C 0.157(2) 0.164(2) 0.304(3) 0.143(12) Uani 1 1 d . U . . .
H18A H 0.095193 0.171315 0.309723 0.171 Uiso 1 1 calc R U . . .
H18B H 0.183708 0.218225 0.350334 0.171 Uiso 1 1 calc R U . . .
C15 C 0.4431(14) 0.1286(11) 0.739(4) 0.140(10) Uani 1 1 d . . . . .
H15A H 0.421849 0.067256 0.769061 0.210 Uiso 1 1 calc R U . . .
H15B H 0.491957 0.146861 0.792204 0.210 Uiso 1 1 calc R U . . .
H15C H 0.460036 0.123848 0.647213 0.210 Uiso 1 1 calc R U . . .
C11 C 0.3117(16) 0.203(2) 0.642(2) 0.095(7) Uani 1 1 d D U . . .
H11A H 0.295808 0.138202 0.617052 0.113 Uiso 1 1 calc R U . . .
H11B H 0.336512 0.234910 0.564606 0.113 Uiso 1 1 calc R U . . .
C19 C 0.1869(16) 0.0632(17) 0.373(2) 0.089(6) Uani 1 1 d . U . . .
H19A H 0.237883 0.071018 0.427486 0.106 Uiso 1 1 calc R U . . .
H19B H 0.141102 0.034691 0.425476 0.106 Uiso 1 1 calc R U . . .
C17 C 0.1839(13) 0.1621(14) 0.169(2) 0.081(5) Uani 1 1 d . U . . .
H17A H 0.244363 0.177909 0.159043 0.097 Uiso 1 1 calc R U . . .
H17B H 0.149185 0.203650 0.113084 0.097 Uiso 1 1 calc R U . . .
C12 C 0.2325(15) 0.2585(16) 0.689(3) 0.100(7) Uani 1 1 d D U . . .
H12A H 0.179042 0.226764 0.664779 0.120 Uiso 1 1 calc R U . . .
H12B H 0.231914 0.324951 0.658467 0.120 Uiso 1 1 calc R U . . .
C13 C 0.2536(14) 0.2493(16) 0.840(3) 0.101(7) Uani 1 1 d D U . . .
H13A H 0.264094 0.313278 0.875549 0.121 Uiso 1 1 calc R U . . .
H13B H 0.203651 0.223222 0.885364 0.121 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
Sn1 Br3 2.597(3) . ?
Sn1 Br3 2.597(3) 2_665 ?
Sn1 Br4 2.5926(10) . ?
Sn1 Br4 2.5926(10) 2_665 ?
Sn1 Br5 2.590(3) . ?
Sn1 Br5 2.590(3) 2_665 ?
Sn2 Br8 2.614(4) 2_655 ?
Sn2 Br8 2.614(4) . ?
Sn2 Br7 2.5828(10) 2_655 ?
Sn2 Br7 2.5827(10) . ?
Sn2 Br6 2.593(4) 2_655 ?
Sn2 Br6 2.593(4) . ?
N9 H9 0.9800 . ?
N9 C14 1.40(3) . ?
N9 C15 1.46(2) . ?
N9 C11 1.49(3) . ?
N10 H10 0.9800 . ?
N10 C16 1.38(3) . ?
N10 C20 1.513(15) . ?
N10 C19 1.50(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.44(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.53(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.63(4) . ?
C18 C17 1.41(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.52(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.55(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 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
Br3 Sn1 Br3 91.07(15) 2_665 . ?
Br4 Sn1 Br3 91.51(9) 2_665 . ?
Br4 Sn1 Br3 91.51(9) . 2_665 ?
Br4 Sn1 Br3 89.26(9) . . ?
Br4 Sn1 Br3 89.26(9) 2_665 2_665 ?
Br4 Sn1 Br4 178.9(2) . 2_665 ?
Br5 Sn1 Br3 89.22(4) . 2_665 ?
Br5 Sn1 Br3 89.22(4) 2_665 . ?
Br5 Sn1 Br3 179.58(14) 2_665 2_665 ?
Br5 Sn1 Br3 179.58(14) . . ?
Br5 Sn1 Br4 88.19(9) . 2_665 ?
Br5 Sn1 Br4 91.03(9) . . ?
Br5 Sn1 Br4 88.19(9) 2_665 . ?
Br5 Sn1 Br4 91.03(9) 2_665 2_665 ?
Br5 Sn1 Br5 90.49(16) 2_665 . ?
Br8 Sn2 Br8 89.92(18) . 2_655 ?
Br7 Sn2 Br8 89.97(12) 2_655 2_655 ?
Br7 Sn2 Br8 89.97(12) . . ?
Br7 Sn2 Br8 90.17(13) 2_655 . ?
Br7 Sn2 Br8 90.17(13) . 2_655 ?
Br7 Sn2 Br7 179.8(3) . 2_655 ?
Br7 Sn2 Br6 90.13(13) 2_655 2_655 ?
Br7 Sn2 Br6 89.73(13) 2_655 . ?
Br7 Sn2 Br6 90.13(13) . . ?
Br7 Sn2 Br6 89.73(13) . 2_655 ?
Br6 Sn2 Br8 89.65(4) . 2_655 ?
Br6 Sn2 Br8 179.57(18) . . ?
Br6 Sn2 Br8 89.65(4) 2_655 . ?
Br6 Sn2 Br8 179.57(18) 2_655 2_655 ?
Br6 Sn2 Br6 90.77(19) . 2_655 ?
C14 N9 H9 107.8 . . ?
C14 N9 C15 113(2) . . ?
C14 N9 C11 105.1(11) . . ?
C15 N9 H9 107.8 . . ?
C15 N9 C11 115(2) . . ?
C11 N9 H9 107.8 . . ?
C16 N10 H10 108.4 . . ?
C16 N10 C20 106(2) . . ?
C16 N10 C19 106.2(13) . . ?
C20 N10 H10 108.4 . . ?
C19 N10 H10 108.4 . . ?
C19 N10 C20 119(3) . . ?
N9 C14 H14A 111.6 . . ?
N9 C14 H14B 111.6 . . ?
N9 C14 C13 100.9(19) . . ?
H14A C14 H14B 109.4 . . ?
C13 C14 H14A 111.6 . . ?
C13 C14 H14B 111.6 . . ?
N10 C16 H16A 110.5 . . ?
N10 C16 H16B 110.5 . . ?
N10 C16 C17 106(2) . . ?
H16A C16 H16B 108.7 . . ?
C17 C16 H16A 110.5 . . ?
C17 C16 H16B 110.5 . . ?
N10 C20 H20A 109.5 . . ?
N10 C20 H20B 109.5 . . ?
N10 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
C17 C18 H18A 110.2 . . ?
C17 C18 H18B 110.2 . . ?
C17 C18 C19 108(3) . . ?
N9 C15 H15A 109.5 . . ?
N9 C15 H15B 109.5 . . ?
N9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N9 C11 H11A 109.9 . . ?
N9 C11 H11B 109.9 . . ?
N9 C11 C12 109(2) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
N10 C19 C18 99.2(18) . . ?
N10 C19 H19A 111.9 . . ?
N10 C19 H19B 111.9 . . ?
C18 C19 H19A 111.9 . . ?
C18 C19 H19B 111.9 . . ?
H19A C19 H19B 109.6 . . ?
C16 C17 H17A 112.4 . . ?
C16 C17 H17B 112.4 . . ?
C18 C17 C16 97(2) . . ?
C18 C17 H17A 112.4 . . ?
C18 C17 H17B 112.4 . . ?
H17A C17 H17B 110.0 . . ?
C11 C12 H12A 112.7 . . ?
C11 C12 H12B 112.7 . . ?
C11 C12 C13 95(2) . . ?
H12A C12 H12B 110.2 . . ?
C13 C12 H12A 112.7 . . ?
C13 C12 H12B 112.7 . . ?
C14 C13 C12 115(2) . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N9 C14 C13 C12 28(3) . . . . ?
N9 C11 C12 C13 -18(3) . . . . ?
N10 C16 C17 C18 -50(3) . . . . ?
C14 N9 C11 C12 37.9(18) . . . . ?
C16 N10 C19 C18 -17(2) . . . . ?
C20 N10 C16 C17 170(2) . . . . ?
C20 N10 C19 C18 -136(2) . . . . ?
C15 N9 C14 C13 -165(2) . . . . ?
C15 N9 C11 C12 163(2) . . . . ?
C11 N9 C14 C13 -38.3(16) . . . . ?
C11 C12 C13 C14 -6(3) . . . . ?
C19 N10 C16 C17 42(2) . . . . ?
C19 C18 C17 C16 37(3) . . . . ?
C17 C18 C19 N10 -16(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.49(4)
2 0.51(4)

####################################################################### 
# 
# 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_mo_77360k_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2210040'
loop_
_audit_author_name
_audit_author_address
Huxinxin
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2022-09-28 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;
_audit_creation_date             2022-09-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br6 Sn, 2(C5 H12 N)'
_chemical_formula_sum            'C10 H24 Br6 N2 Sn'
_chemical_formula_weight         770.46
_chemical_melting_point          ?
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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.9302(10)
_cell_length_b                   15.5956(9)
_cell_length_c                   10.1118(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2196.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3802
_cell_measurement_temperature    360
_cell_measurement_theta_max      22.19
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    12.068
_exptl_absorpt_correction_T_max  0.0160
_exptl_absorpt_correction_T_min  0.0025
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1288 before and 0.0750 after correction.
The Ratio of minimum to maximum transmission is 0.1562.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0921
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            40197
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         3.203
_diffrn_ambient_temperature      360
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1361
_reflns_number_total             2661
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         2661
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.016
_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)+(0.0456P)²+3.4664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1301
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C12-C12_$1
 1.5 with sigma of 0.02
2. Others
 Fixed Sof: H14A(0.5) H14B(0.5) H14C(0.5) H11A(0.5) H11B(0.5) H11C(0.5)
3.a Riding coordinates:
 C14(H14A,H14B,H14C), C11(H11A,H11B,H11C)
3.b Ternary CH refined with riding coordinates:
 N7(H7), N8(H8)
3.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Sn1 Sn 0.000000 0.500000 1.000000 0.0793(3) Uani 1 4 d S T P . .
Sn2 Sn 0.500000 0.500000 0.500000 0.0882(3) Uani 1 4 d S T P . .
Br3 Br -0.00183(9) 0.66629(7) 1.000000 0.1046(4) Uani 1 2 d S T P . .
Br4 Br 0.13291(6) 0.49775(6) 1.18016(10) 0.1083(3) Uani 1 1 d . . . . .
Br5 Br 0.56255(8) 0.39572(7) 0.31856(12) 0.1314(4) Uani 1 1 d . . . . .
Br6 Br 0.33562(10) 0.42259(10) 0.500000 0.1373(6) Uani 1 2 d S T P . .
N7 N 0.4899(11) 0.2041(7) 0.500000 0.145(5) Uani 1 2 d S T P . .
H7 H 0.490418 0.266911 0.499998 0.174 Uiso 1 2 calc R U P . .
N8 N 0.2953(9) 0.3734(9) 1.000000 0.135(4) Uani 1 2 d S T P . .
H8 H 0.232479 0.401751 0.999999 0.162 Uiso 1 2 calc R U P . .
C14 C 0.5946(11) 0.1730(11) 0.500000 0.207(11) Uani 1 2 d S T P . .
H14A H 0.597647 0.117578 0.458970 0.310 Uiso 0.5 1 d R U P A -1
H14B H 0.634067 0.212558 0.451620 0.310 Uiso 0.5 1 d R U P A -1
H14C H 0.617357 0.168978 0.589410 0.310 Uiso 0.5 1 d R U P A -1
C10 C 0.3040(10) 0.3193(9) 0.8886(12) 0.172(6) Uani 1 1 d . . . . .
H10A H 0.370504 0.303943 0.873304 0.206 Uiso 1 1 calc R U . . .
H10B H 0.278828 0.347023 0.809989 0.206 Uiso 1 1 calc R U . . .
C11 C 0.3725(13) 0.4377(14) 1.000000 0.207(10) Uani 1 2 d S T P . .
H11A H 0.433144 0.409831 0.986110 0.310 Uiso 0.5 1 d R U P B -1
H11B H 0.361364 0.478291 0.930370 0.310 Uiso 0.5 1 d R U P B -1
H11C H 0.373294 0.466911 1.083520 0.310 Uiso 0.5 1 d R U P B -1
C9 C 0.2458(8) 0.2422(8) 0.9234(15) 0.198(8) Uani 1 1 d . . . . .
H9A H 0.275127 0.190337 0.889001 0.238 Uiso 1 1 calc R U . . .
H9B H 0.181049 0.246874 0.888999 0.238 Uiso 1 1 calc R U . . .
C12 C 0.3345(9) 0.1730(9) 0.4290(8) 0.206(8) Uani 1 1 d D . . . .
H12A H 0.299787 0.222342 0.395476 0.247 Uiso 1 1 calc R U . . .
H12B H 0.304222 0.121360 0.395476 0.247 Uiso 1 1 calc R U . . .
C13 C 0.4425(10) 0.1768(10) 0.3857(13) 0.190(6) Uani 1 1 d . . . . .
H13A H 0.465141 0.120779 0.357964 0.228 Uiso 1 1 calc R U . . .
H13B H 0.451579 0.217193 0.313867 0.228 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
Sn1 Br3 2.5936(11) . ?
Sn1 Br3 2.5936(11) 5_567 ?
Sn1 Br4 2.5977(9) 6_557 ?
Sn1 Br4 2.5977(9) 5_567 ?
Sn1 Br4 2.5977(9) 2_565 ?
Sn1 Br4 2.5976(9) . ?
Sn2 Br5 2.6019(10) . ?
Sn2 Br5 2.6020(10) 5_666 ?
Sn2 Br5 2.6020(10) 6_556 ?
Sn2 Br5 2.6020(10) 2_665 ?
Sn2 Br6 2.5886(14) 5_666 ?
Sn2 Br6 2.5886(14) . ?
N7 H7 0.9800 . ?
N7 C14 1.537(18) . ?
N7 C13 1.398(13) 6_556 ?
N7 C13 1.398(13) . ?
N8 H8 0.9800 . ?
N8 C10 1.412(12) . ?
N8 C10 1.412(12) 6_557 ?
N8 C11 1.47(2) . ?
C14 H14A 0.9598 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.493(17) . ?
C11 H11A 0.9601 . ?
C11 H11B 0.9599 . ?
C11 H11C 0.9600 . ?
C9 C9 1.55(3) 6_557 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C12 C12 1.435(17) 6_556 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.568(14) . ?
C13 H13A 0.9700 . ?
C13 H13B 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
Br3 Sn1 Br3 180.0 . 5_567 ?
Br3 Sn1 Br4 88.83(3) 5_567 6_557 ?
Br3 Sn1 Br4 88.83(3) . 5_567 ?
Br3 Sn1 Br4 91.17(3) 5_567 5_567 ?
Br3 Sn1 Br4 88.83(3) 5_567 . ?
Br3 Sn1 Br4 88.83(3) . 2_565 ?
Br3 Sn1 Br4 91.17(3) . 6_557 ?
Br3 Sn1 Br4 91.17(3) . . ?
Br3 Sn1 Br4 91.17(3) 5_567 2_565 ?
Br4 Sn1 Br4 89.06(5) . 6_557 ?
Br4 Sn1 Br4 89.06(5) 5_567 2_565 ?
Br4 Sn1 Br4 180.00(4) . 5_567 ?
Br4 Sn1 Br4 90.94(5) . 2_565 ?
Br4 Sn1 Br4 180.0 6_557 2_565 ?
Br4 Sn1 Br4 90.94(5) 5_567 6_557 ?
Br5 Sn2 Br5 180.0 . 5_666 ?
Br5 Sn2 Br5 90.32(5) . 2_665 ?
Br5 Sn2 Br5 89.68(5) 5_666 2_665 ?
Br5 Sn2 Br5 90.32(5) 5_666 6_556 ?
Br5 Sn2 Br5 89.68(5) . 6_556 ?
Br5 Sn2 Br5 180.00(4) 2_665 6_556 ?
Br6 Sn2 Br5 89.73(4) 5_666 . ?
Br6 Sn2 Br5 89.73(4) . 2_665 ?
Br6 Sn2 Br5 89.73(4) 5_666 6_556 ?
Br6 Sn2 Br5 90.27(4) . . ?
Br6 Sn2 Br5 90.27(4) . 6_556 ?
Br6 Sn2 Br5 90.27(4) 5_666 2_665 ?
Br6 Sn2 Br5 90.27(4) 5_666 5_666 ?
Br6 Sn2 Br5 89.73(4) . 5_666 ?
Br6 Sn2 Br6 180.0 . 5_666 ?
C14 N7 H7 107.9 . . ?
C13 N7 H7 107.9 6_556 . ?
C13 N7 H7 107.9 . . ?
C13 N7 C14 110.6(10) . . ?
C13 N7 C14 110.6(10) 6_556 . ?
C13 N7 C13 111.6(16) . 6_556 ?
C10 N8 H8 110.2 . . ?
C10 N8 H8 110.2 6_557 . ?
C10 N8 C10 105.8(14) 6_557 . ?
C10 N8 C11 110.1(10) 6_557 . ?
C10 N8 C11 110.1(10) . . ?
C11 N8 H8 110.2 . . ?
N7 C14 H14A 109.0 . . ?
N7 C14 H14B 109.9 . . ?
N7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N8 C10 H10A 110.9 . . ?
N8 C10 H10B 110.9 . . ?
N8 C10 C9 104.3(13) . . ?
H10A C10 H10B 108.9 . . ?
C9 C10 H10A 110.9 . . ?
C9 C10 H10B 110.9 . . ?
N8 C11 H11A 109.6 . . ?
N8 C11 H11B 109.4 . . ?
N8 C11 H11C 109.4 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C9 C9 103.7(8) . 6_557 ?
C10 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
C9 C9 H9A 111.0 6_557 . ?
C9 C9 H9B 111.0 6_557 . ?
H9A C9 H9B 109.0 . . ?
C12 C12 H12A 110.5 6_556 . ?
C12 C12 H12B 110.5 6_556 . ?
C12 C12 C13 106.2(6) 6_556 . ?
H12A C12 H12B 108.7 . . ?
C13 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
N7 C13 C12 103.5(11) . . ?
N7 C13 H13A 111.1 . . ?
N7 C13 H13B 111.1 . . ?
C12 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N8 C10 C9 C9 -24.7(9) . . . 6_557 ?
C14 N7 C13 C12 153.8(11) . . . . ?
C10 N8 C10 C9 42.2(17) 6_557 . . . ?
C11 N8 C10 C9 161.2(11) . . . . ?
C12 C12 C13 N7 -17.1(12) 6_556 . . . ?
C13 N7 C13 C12 30(2) 6_556 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
