# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_ceph031
_database_code_depnum_ccdc_archive 'CCDC 2358999'
loop_
_audit_author_name
_audit_author_address
'Chartrand '
;University of Montreal
Canada
;
_audit_update_record             
;
2024-05-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2023-09-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
daniel.chartrand.1@umontreal.ca
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br6 Sn, 2(C9 H14 N)'
_chemical_formula_sum            'C18 H28 Br6 N2 Sn'
_chemical_formula_weight         870.57
_chemical_absolute_configuration ad
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.5715(3)
_cell_length_b                   17.9623(7)
_cell_length_c                   20.2642(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2756.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    150
_cell_measurement_theta_max      61.346
_cell_measurement_theta_min      4.687
_shelx_estimated_absorpt_T_max   0.451
_shelx_estimated_absorpt_T_min   0.288
_exptl_absorpt_coefficient_mu    11.843
_exptl_absorpt_correction_T_max  0.1578
_exptl_absorpt_correction_T_min  0.0473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1584 before and 0.0821 after correction.
The Ratio of minimum to maximum transmission is 0.2997.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.098
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22042
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         62.330
_diffrn_reflns_theta_min         4.359
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                5787
_reflns_number_total             6331
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_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         0.866
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.069(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         6331
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+0.4329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0652
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.931(8)
 0.069(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 H1Aa-N1A \\sim N1A-H1Ab \\sim N1A-H1Ac \\sim H1Ba-N1B \\sim N1B-H1Bb \\sim
N1B-H1Bc
 with sigma of 0.02
 H1Ac-H1Aa \\sim H1Aa-H1Ab \\sim H1Ac-H1Ab \\sim H1Bc-H1Ba \\sim H1Ba-H1Bb
\\sim H1Bc-H1Bb
 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C3A(H3A), C3B(H3B)
4.b Secondary CH2 refined with riding coordinates:
 C2A(H2Aa,H2Ab), C2B(H2Ba,H2Bb)
4.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C5B(H5B), C6B(H6B),
 C7B(H7B), C8B(H8B), C9B(H9B)
4.d Idealised Me refined as rotating group:
 C1A(H1Ad,H1Ae,H1Af), C1B(H1Bd,H1Be,H1Bf)
;
_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 0.47440(5) 0.43720(2) 0.49550(2) 0.03373(9) Uani 1 1 d . . . . .
Br1 Br 0.21431(8) 0.36356(3) 0.55089(3) 0.04443(15) Uani 1 1 d . . . . .
Br2 Br 0.70387(7) 0.35026(3) 0.55315(3) 0.04028(14) Uani 1 1 d . . . . .
Br3 Br 0.49606(8) 0.52480(3) 0.59617(3) 0.04842(15) Uani 1 1 d . . . . .
Br4 Br 0.46736(9) 0.34448(4) 0.39750(3) 0.05332(17) Uani 1 1 d . . . . .
Br5 Br 0.23865(8) 0.52238(3) 0.44313(3) 0.04374(15) Uani 1 1 d . . . . .
Br6 Br 0.72704(8) 0.50831(3) 0.43790(3) 0.04420(15) Uani 1 1 d . . . . .
N1A N 0.4235(7) 0.2007(2) 0.5885(2) 0.0411(11) Uani 1 1 d D . . . .
H1AA H 0.310(4) 0.192(3) 0.580(3) 0.049 Uiso 1 1 d D U . . .
H1AB H 0.483(6) 0.174(2) 0.559(2) 0.049 Uiso 1 1 d D U . . .
H1AC H 0.439(6) 0.2471(17) 0.573(2) 0.049 Uiso 1 1 d D U . . .
C1A C 0.5901(10) 0.0943(4) 0.7391(3) 0.0649(19) Uani 1 1 d . . . . .
H1AD H 0.716979 0.098221 0.730295 0.097 Uiso 1 1 calc R U . . .
H1AE H 0.562335 0.043717 0.754044 0.097 Uiso 1 1 calc R U . . .
H1AF H 0.556900 0.130045 0.773465 0.097 Uiso 1 1 calc R U . . .
C2A C 0.4878(8) 0.1111(3) 0.6764(3) 0.0440(13) Uani 1 1 d . . . . .
H2AA H 0.360778 0.101222 0.684053 0.053 Uiso 1 1 calc R U . . .
H2AB H 0.528617 0.077509 0.640824 0.053 Uiso 1 1 calc R U . . .
C3A C 0.5117(7) 0.1920(3) 0.6545(2) 0.0381(11) Uani 1 1 d . . . . .
H3A H 0.640956 0.201132 0.648435 0.046 Uiso 1 1 calc R U . . .
C4A C 0.4426(9) 0.2491(3) 0.7021(3) 0.0424(14) Uani 1 1 d . . . . .
C5A C 0.5546(11) 0.3024(4) 0.7272(3) 0.0629(19) Uani 1 1 d . . . . .
H5A H 0.675082 0.303262 0.714130 0.075 Uiso 1 1 calc R U . . .
C6A C 0.4909(16) 0.3553(4) 0.7722(4) 0.086(3) Uani 1 1 d . . . . .
H6A H 0.568240 0.391885 0.789821 0.103 Uiso 1 1 calc R U . . .
C7A C 0.3175(16) 0.3541(4) 0.7905(4) 0.085(3) Uani 1 1 d . . . . .
H7A H 0.273736 0.391136 0.819754 0.102 Uiso 1 1 calc R U . . .
C8A C 0.2060(12) 0.3002(4) 0.7673(3) 0.074(2) Uani 1 1 d . . . . .
H8A H 0.086867 0.298236 0.781829 0.088 Uiso 1 1 calc R U . . .
C9A C 0.2672(10) 0.2497(3) 0.7234(3) 0.0533(16) Uani 1 1 d . . . . .
H9A H 0.188099 0.213311 0.706448 0.064 Uiso 1 1 calc R U . . .
N1B N 0.9623(7) 0.5213(2) 0.5815(2) 0.0447(11) Uani 1 1 d D . . . .
H1BA H 0.962(7) 0.4720(17) 0.588(2) 0.054 Uiso 1 1 d D U . . .
H1BB H 1.016(6) 0.526(3) 0.5430(19) 0.054 Uiso 1 1 d D U . . .
H1BC H 0.849(4) 0.531(3) 0.574(3) 0.054 Uiso 1 1 d D U . . .
C1B C 0.9275(11) 0.4815(4) 0.7237(3) 0.0656(19) Uani 1 1 d . . . . .
H1BD H 0.877064 0.479896 0.768231 0.098 Uiso 1 1 calc R U . . .
H1BE H 1.050951 0.465193 0.725270 0.098 Uiso 1 1 calc R U . . .
H1BF H 0.860264 0.448437 0.694612 0.098 Uiso 1 1 calc R U . . .
C2B C 0.9186(9) 0.5610(3) 0.6973(3) 0.0470(13) Uani 1 1 d . . . . .
H2BA H 0.793708 0.573437 0.687997 0.056 Uiso 1 1 calc R U . . .
H2BB H 0.960717 0.595403 0.732093 0.056 Uiso 1 1 calc R U . . .
C3B C 1.0262(8) 0.5741(3) 0.6353(3) 0.0415(12) Uani 1 1 d . . . . .
H3B H 1.152285 0.561906 0.645290 0.050 Uiso 1 1 calc R U . . .
C4B C 1.0183(8) 0.6531(3) 0.6104(3) 0.0403(12) Uani 1 1 d . . . . .
C5B C 1.1665(9) 0.6975(3) 0.6147(3) 0.0503(15) Uani 1 1 d . . . . .
H5B H 1.273051 0.677730 0.632238 0.060 Uiso 1 1 calc R U . . .
C6B C 1.1607(10) 0.7706(3) 0.5938(3) 0.0570(16) Uani 1 1 d . . . . .
H6B H 1.262940 0.800952 0.597677 0.068 Uiso 1 1 calc R U . . .
C7B C 1.0113(10) 0.7996(3) 0.5677(3) 0.0586(17) Uani 1 1 d . . . . .
H7B H 1.009145 0.850172 0.553904 0.070 Uiso 1 1 calc R U . . .
C8B C 0.8615(10) 0.7560(3) 0.5611(3) 0.0588(18) Uani 1 1 d . . . . .
H8B H 0.757539 0.775982 0.541762 0.071 Uiso 1 1 calc R U . . .
C9B C 0.8645(9) 0.6826(3) 0.5831(3) 0.0510(15) Uani 1 1 d . . . . .
H9B H 0.761605 0.652625 0.579454 0.061 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 Br1 2.6244(6) . ?
Sn1 Br2 2.6119(6) . ?
Sn1 Br3 2.5815(6) . ?
Sn1 Br4 2.5924(7) . ?
Sn1 Br5 2.5795(6) . ?
Sn1 Br6 2.5794(6) . ?
N1A H1AA 0.89(3) . ?
N1A H1AB 0.89(3) . ?
N1A H1AC 0.90(3) . ?
N1A C3A 1.503(7) . ?
C1A H1AD 0.9800 . ?
C1A H1AE 0.9800 . ?
C1A H1AF 0.9800 . ?
C1A C2A 1.518(8) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.530(7) . ?
C3A H3A 1.0000 . ?
C3A C4A 1.502(7) . ?
C4A C5A 1.376(8) . ?
C4A C9A 1.397(9) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.403(11) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.364(14) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.369(13) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.352(9) . ?
C9A H9A 0.9500 . ?
N1B H1BA 0.90(3) . ?
N1B H1BB 0.88(3) . ?
N1B H1BC 0.89(3) . ?
N1B C3B 1.524(7) . ?
C1B H1BD 0.9800 . ?
C1B H1BE 0.9800 . ?
C1B H1BF 0.9800 . ?
C1B C2B 1.526(8) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B C3B 1.516(8) . ?
C3B H3B 1.0000 . ?
C3B C4B 1.508(7) . ?
C4B C5B 1.380(8) . ?
C4B C9B 1.395(8) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.381(8) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.352(10) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.386(10) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.391(8) . ?
C9B H9B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br2 Sn1 Br1 90.37(2) . . ?
Br3 Sn1 Br1 90.97(2) . . ?
Br3 Sn1 Br2 88.21(2) . . ?
Br3 Sn1 Br4 176.60(3) . . ?
Br4 Sn1 Br1 89.33(2) . . ?
Br4 Sn1 Br2 88.41(2) . . ?
Br5 Sn1 Br1 87.46(2) . . ?
Br5 Sn1 Br2 177.42(2) . . ?
Br5 Sn1 Br3 90.43(2) . . ?
Br5 Sn1 Br4 92.96(2) . . ?
Br6 Sn1 Br1 178.40(3) . . ?
Br6 Sn1 Br2 90.30(2) . . ?
Br6 Sn1 Br3 90.50(2) . . ?
Br6 Sn1 Br4 89.24(2) . . ?
Br6 Sn1 Br5 91.91(2) . . ?
H1AA N1A H1AB 106(3) . . ?
H1AA N1A H1AC 102(3) . . ?
H1AB N1A H1AC 101(3) . . ?
C3A N1A H1AA 125(4) . . ?
C3A N1A H1AB 109(4) . . ?
C3A N1A H1AC 111(3) . . ?
H1AD C1A H1AE 109.5 . . ?
H1AD C1A H1AF 109.5 . . ?
H1AE C1A H1AF 109.5 . . ?
C2A C1A H1AD 109.5 . . ?
C2A C1A H1AE 109.5 . . ?
C2A C1A H1AF 109.5 . . ?
C1A C2A H2AA 109.3 . . ?
C1A C2A H2AB 109.3 . . ?
C1A C2A C3A 111.8(5) . . ?
H2AA C2A H2AB 107.9 . . ?
C3A C2A H2AA 109.3 . . ?
C3A C2A H2AB 109.3 . . ?
N1A C3A C2A 107.7(4) . . ?
N1A C3A H3A 107.9 . . ?
C2A C3A H3A 107.9 . . ?
C4A C3A N1A 110.2(4) . . ?
C4A C3A C2A 114.9(4) . . ?
C4A C3A H3A 107.9 . . ?
C5A C4A C3A 119.9(6) . . ?
C5A C4A C9A 117.8(6) . . ?
C9A C4A C3A 122.3(5) . . ?
C4A C5A H5A 120.0 . . ?
C4A C5A C6A 120.0(8) . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A H6A 120.1 . . ?
C7A C6A C5A 119.8(8) . . ?
C7A C6A H6A 120.1 . . ?
C6A C7A H7A 119.7 . . ?
C6A C7A C8A 120.7(7) . . ?
C8A C7A H7A 119.7 . . ?
C7A C8A H8A 120.3 . . ?
C9A C8A C7A 119.4(8) . . ?
C9A C8A H8A 120.3 . . ?
C4A C9A H9A 118.9 . . ?
C8A C9A C4A 122.2(7) . . ?
C8A C9A H9A 118.9 . . ?
H1BA N1B H1BB 104(3) . . ?
H1BA N1B H1BC 103(3) . . ?
H1BB N1B H1BC 106(3) . . ?
C3B N1B H1BA 120(4) . . ?
C3B N1B H1BB 115(4) . . ?
C3B N1B H1BC 108(4) . . ?
H1BD C1B H1BE 109.5 . . ?
H1BD C1B H1BF 109.5 . . ?
H1BE C1B H1BF 109.5 . . ?
C2B C1B H1BD 109.5 . . ?
C2B C1B H1BE 109.5 . . ?
C2B C1B H1BF 109.5 . . ?
C1B C2B H2BA 108.7 . . ?
C1B C2B H2BB 108.7 . . ?
H2BA C2B H2BB 107.6 . . ?
C3B C2B C1B 114.3(5) . . ?
C3B C2B H2BA 108.7 . . ?
C3B C2B H2BB 108.7 . . ?
N1B C3B H3B 108.1 . . ?
C2B C3B N1B 109.0(5) . . ?
C2B C3B H3B 108.1 . . ?
C4B C3B N1B 109.5(4) . . ?
C4B C3B C2B 113.7(4) . . ?
C4B C3B H3B 108.1 . . ?
C5B C4B C3B 119.4(5) . . ?
C5B C4B C9B 119.0(5) . . ?
C9B C4B C3B 121.6(5) . . ?
C4B C5B H5B 119.9 . . ?
C4B C5B C6B 120.3(6) . . ?
C6B C5B H5B 119.9 . . ?
C5B C6B H6B 119.6 . . ?
C7B C6B C5B 120.9(6) . . ?
C7B C6B H6B 119.6 . . ?
C6B C7B H7B 119.9 . . ?
C6B C7B C8B 120.3(6) . . ?
C8B C7B H7B 119.9 . . ?
C7B C8B H8B 120.3 . . ?
C7B C8B C9B 119.5(6) . . ?
C9B C8B H8B 120.3 . . ?
C4B C9B H9B 120.0 . . ?
C8B C9B C4B 120.1(6) . . ?
C8B C9B H9B 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1AA Br4 0.89(3) 2.71(3) 3.559(5) 159(5) 4_456 yes
N1A H1AB Br1 0.89(3) 2.91(3) 3.763(5) 160(4) 4_556 yes
N1A H1AC Br1 0.90(3) 2.73(4) 3.413(5) 133(4) . yes
N1A H1AC Br2 0.90(3) 2.76(4) 3.499(5) 140(4) . yes
N1B H1BA Br1 0.90(3) 2.83(4) 3.471(5) 130(4) 1_655 yes
N1B H1BB Br5 0.88(3) 2.63(3) 3.499(5) 166(4) 1_655 yes
N1B H1BC Br3 0.89(3) 2.71(3) 3.543(5) 156(4) . yes
N1B H1BC Br6 0.89(3) 2.94(5) 3.420(5) 116(4) . yes

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
N1A C3A C4A C5A -116.2(6) . . . . ?
N1A C3A C4A C9A 65.2(7) . . . . ?
C1A C2A C3A N1A 173.6(5) . . . . ?
C1A C2A C3A C4A -63.2(7) . . . . ?
C2A C3A C4A C5A 121.9(6) . . . . ?
C2A C3A C4A C9A -56.7(7) . . . . ?
C3A C4A C5A C6A -179.3(6) . . . . ?
C3A C4A C9A C8A 178.5(6) . . . . ?
C4A C5A C6A C7A -0.4(12) . . . . ?
C5A C4A C9A C8A -0.1(10) . . . . ?
C5A C6A C7A C8A 2.3(13) . . . . ?
C6A C7A C8A C9A -3.0(12) . . . . ?
C7A C8A C9A C4A 1.9(11) . . . . ?
C9A C4A C5A C6A -0.7(10) . . . . ?
N1B C3B C4B C5B -127.5(6) . . . . ?
N1B C3B C4B C9B 52.6(7) . . . . ?
C1B C2B C3B N1B 58.4(7) . . . . ?
C1B C2B C3B C4B -179.1(6) . . . . ?
C2B C3B C4B C5B 110.3(6) . . . . ?
C2B C3B C4B C9B -69.6(7) . . . . ?
C3B C4B C5B C6B -178.3(6) . . . . ?
C3B C4B C9B C8B 179.4(5) . . . . ?
C4B C5B C6B C7B -1.1(10) . . . . ?
C5B C4B C9B C8B -0.5(9) . . . . ?
C5B C6B C7B C8B -0.6(11) . . . . ?
C6B C7B C8B C9B 1.7(11) . . . . ?
C7B C8B C9B C4B -1.1(10) . . . . ?
C9B C4B C5B C6B 1.6(9) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop with paratone'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.931(8)
2 0.069(8)

####################################################################### 
# 
# 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_ceph024
_database_code_depnum_ccdc_archive 'CCDC 2359000'
loop_
_audit_author_name
_audit_author_address
'Chartrand '
;University of Montreal
Canada
;
_audit_update_record             
;
2024-05-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2023-09-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
daniel.chartrand.1@umontreal.ca
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br6 Sn, 2(C9 H14 N)'
_chemical_formula_sum            'C18 H28 Br6 N2 Sn'
_chemical_formula_weight         870.57
_chemical_absolute_configuration ad
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.5756(3)
_cell_length_b                   17.9704(6)
_cell_length_c                   20.2660(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2758.94(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9221
_cell_measurement_temperature    150
_cell_measurement_theta_max      59.180
_cell_measurement_theta_min      2.860
_shelx_estimated_absorpt_T_max   0.718
_shelx_estimated_absorpt_T_min   0.537
_exptl_absorpt_coefficient_mu    11.831
_exptl_absorpt_correction_T_max  0.1071
_exptl_absorpt_correction_T_min  0.0208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1596 before and 0.0982 after correction.
The Ratio of minimum to maximum transmission is 0.1942.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29150
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         65.914
_diffrn_reflns_theta_min         2.859
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                4884
_reflns_number_total             6939
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_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         1.184
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.147
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.058(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         6939
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0649P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1242
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.942(13)
 0.058(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C3A(H3A), C3B(H3B)
3.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C2B(H2BA,H2BB)
3.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C5B(H5B), C6B(H6B),
 C7B(H7B), C8B(H8B), C9B(H9B)
3.d Idealised Me refined as rotating group:
 N1A(H1AA,H1AB,H1AC), C1A(H1AD,H1AE,H1AF), N1B(H1BA,H1BB,H1BC), C1B(H1BD,H1BE,
 H1BF)
;
_atom_sites_solution_hydrogens   geom
_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 0.52409(8) 0.56322(3) 0.50511(3) 0.04884(18) Uani 1 1 d . . . . .
Br1 Br 0.78378(13) 0.63653(5) 0.44950(6) 0.0619(3) Uani 1 1 d . . . . .
Br2 Br 0.29401(13) 0.64918(6) 0.44700(6) 0.0563(3) Uani 1 1 d . . . . .
Br3 Br 0.50366(14) 0.47467(6) 0.40496(6) 0.0659(3) Uani 1 1 d . . . . .
Br4 Br 0.53054(16) 0.65633(7) 0.60281(6) 0.0724(3) Uani 1 1 d . . . . .
Br5 Br 0.75990(13) 0.47854(6) 0.55803(6) 0.0615(3) Uani 1 1 d . . . . .
Br6 Br 0.27197(13) 0.49205(6) 0.56302(6) 0.0606(3) Uani 1 1 d . . . . .
N1A N 0.5736(12) 0.7989(5) 0.4112(4) 0.058(2) Uani 1 1 d . . . . .
H1AA H 0.691291 0.808155 0.407583 0.069 Uiso 1 1 calc R U . . .
H1AB H 0.556922 0.751423 0.425561 0.069 Uiso 1 1 calc R U . . .
H1AC H 0.524867 0.831230 0.440565 0.069 Uiso 1 1 calc R U . . .
C1A C 0.4139(19) 0.9048(8) 0.2594(6) 0.085(4) Uani 1 1 d . . . . .
H1AD H 0.326843 0.865569 0.251177 0.128 Uiso 1 1 calc R U . . .
H1AE H 0.497470 0.906917 0.222484 0.128 Uiso 1 1 calc R U . . .
H1AF H 0.353460 0.952815 0.263489 0.128 Uiso 1 1 calc R U . . .
C2A C 0.5132(15) 0.8881(5) 0.3228(5) 0.062(2) Uani 1 1 d . . . . .
H2AA H 0.640638 0.897372 0.315905 0.075 Uiso 1 1 calc R U . . .
H2AB H 0.471649 0.922089 0.357966 0.075 Uiso 1 1 calc R U . . .
C3A C 0.4872(13) 0.8086(5) 0.3450(4) 0.053(2) Uani 1 1 d . . . . .
H3A H 0.357669 0.800088 0.350721 0.064 Uiso 1 1 calc R U . . .
C4A C 0.5555(17) 0.7508(5) 0.2974(5) 0.062(3) Uani 1 1 d . . . . .
C5A C 0.445(2) 0.6972(8) 0.2737(6) 0.091(4) Uani 1 1 d . . . . .
H5A H 0.326051 0.696068 0.288212 0.109 Uiso 1 1 calc R U . . .
C6A C 0.504(3) 0.6439(7) 0.2287(7) 0.101(5) Uani 1 1 d . . . . .
H6A H 0.425742 0.607399 0.211392 0.121 Uiso 1 1 calc R U . . .
C7A C 0.682(3) 0.6461(8) 0.2099(7) 0.100(5) Uani 1 1 d . . . . .
H7A H 0.725944 0.609174 0.180590 0.120 Uiso 1 1 calc R U . . .
C8A C 0.793(2) 0.6994(8) 0.2323(6) 0.092(4) Uani 1 1 d . . . . .
H8A H 0.912276 0.701685 0.217491 0.110 Uiso 1 1 calc R U . . .
C9A C 0.7294(19) 0.7496(7) 0.2768(6) 0.077(3) Uani 1 1 d . . . . .
H9A H 0.808336 0.785535 0.294507 0.092 Uiso 1 1 calc R U . . .
N1B N 0.0367(11) 0.4786(4) 0.4189(4) 0.0572(19) Uani 1 1 d . . . . .
H1BA H 0.014654 0.526303 0.406300 0.069 Uiso 1 1 calc R U . . .
H1BB H 0.154844 0.472454 0.425020 0.069 Uiso 1 1 calc R U . . .
H1BC H -0.021065 0.468837 0.457308 0.069 Uiso 1 1 calc R U . . .
C1B C 0.0695(19) 0.5189(7) 0.2766(7) 0.084(4) Uani 1 1 d . . . . .
H1BD H 0.106160 0.519711 0.230264 0.126 Uiso 1 1 calc R U . . .
H1BE H 0.147988 0.550868 0.302569 0.126 Uiso 1 1 calc R U . . .
H1BF H -0.052027 0.537143 0.280266 0.126 Uiso 1 1 calc R U . . .
C2B C 0.0794(15) 0.4391(6) 0.3029(5) 0.065(3) Uani 1 1 d . . . . .
H2BA H 0.037123 0.404804 0.268039 0.078 Uiso 1 1 calc R U . . .
H2BB H 0.204465 0.426809 0.311859 0.078 Uiso 1 1 calc R U . . .
C3B C -0.0275(14) 0.4252(5) 0.3653(5) 0.060(2) Uani 1 1 d . . . . .
H3B H -0.153735 0.437164 0.355628 0.072 Uiso 1 1 calc R U . . .
C4B C -0.0189(14) 0.3463(5) 0.3906(5) 0.057(2) Uani 1 1 d . . . . .
C5B C -0.1667(15) 0.3028(6) 0.3852(6) 0.068(3) Uani 1 1 d . . . . .
H5B H -0.273108 0.322431 0.367625 0.081 Uiso 1 1 calc R U . . .
C6B C -0.1573(18) 0.2280(6) 0.4064(7) 0.075(3) Uani 1 1 d . . . . .
H6B H -0.257877 0.196776 0.402163 0.090 Uiso 1 1 calc R U . . .
C7B C -0.0075(18) 0.2004(6) 0.4327(6) 0.075(3) Uani 1 1 d . . . . .
H7B H -0.003358 0.149968 0.446710 0.090 Uiso 1 1 calc R U . . .
C8B C 0.1362(19) 0.2438(6) 0.4392(7) 0.077(3) Uani 1 1 d . . . . .
H8B H 0.239965 0.224112 0.458934 0.093 Uiso 1 1 calc R U . . .
C9B C 0.1345(17) 0.3175(6) 0.4171(7) 0.077(3) Uani 1 1 d . . . . .
H9B H 0.237506 0.347430 0.420250 0.093 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 Br1 2.6222(11) . ?
Sn1 Br2 2.6099(11) . ?
Sn1 Br3 2.5836(12) . ?
Sn1 Br4 2.5926(12) . ?
Sn1 Br5 2.5802(11) . ?
Sn1 Br6 2.5808(12) . ?
N1A H1AA 0.9100 . ?
N1A H1AB 0.9100 . ?
N1A H1AC 0.9100 . ?
N1A C3A 1.503(12) . ?
C1A H1AD 0.9800 . ?
C1A H1AE 0.9800 . ?
C1A H1AF 0.9800 . ?
C1A C2A 1.520(15) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.510(13) . ?
C3A H3A 1.0000 . ?
C3A C4A 1.508(13) . ?
C4A C5A 1.362(17) . ?
C4A C9A 1.382(18) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.40(2) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.40(3) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.35(2) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.366(17) . ?
C9A H9A 0.9500 . ?
N1B H1BA 0.9100 . ?
N1B H1BB 0.9100 . ?
N1B H1BC 0.9100 . ?
N1B C3B 1.528(13) . ?
C1B H1BD 0.9800 . ?
C1B H1BE 0.9800 . ?
C1B H1BF 0.9800 . ?
C1B C2B 1.531(16) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B C3B 1.523(15) . ?
C3B H3B 1.0000 . ?
C3B C4B 1.509(14) . ?
C4B C5B 1.370(15) . ?
C4B C9B 1.380(16) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.412(15) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.348(18) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.346(18) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.399(16) . ?
C9B H9B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br2 Sn1 Br1 90.56(4) . . ?
Br3 Sn1 Br1 90.96(4) . . ?
Br3 Sn1 Br2 88.28(4) . . ?
Br3 Sn1 Br4 176.84(5) . . ?
Br4 Sn1 Br1 89.42(4) . . ?
Br4 Sn1 Br2 88.58(4) . . ?
Br5 Sn1 Br1 87.45(4) . . ?
Br5 Sn1 Br2 177.52(5) . . ?
Br5 Sn1 Br3 90.27(4) . . ?
Br5 Sn1 Br4 92.88(4) . . ?
Br5 Sn1 Br6 91.78(4) . . ?
Br6 Sn1 Br1 178.41(5) . . ?
Br6 Sn1 Br2 90.24(4) . . ?
Br6 Sn1 Br3 90.44(4) . . ?
Br6 Sn1 Br4 89.23(4) . . ?
H1AA N1A H1AB 109.5 . . ?
H1AA N1A H1AC 109.5 . . ?
H1AB N1A H1AC 109.5 . . ?
C3A N1A H1AA 109.5 . . ?
C3A N1A H1AB 109.5 . . ?
C3A N1A H1AC 109.5 . . ?
H1AD C1A H1AE 109.5 . . ?
H1AD C1A H1AF 109.5 . . ?
H1AE C1A H1AF 109.5 . . ?
C2A C1A H1AD 109.5 . . ?
C2A C1A H1AE 109.5 . . ?
C2A C1A H1AF 109.5 . . ?
C1A C2A H2AA 109.2 . . ?
C1A C2A H2AB 109.2 . . ?
H2AA C2A H2AB 107.9 . . ?
C3A C2A C1A 112.0(10) . . ?
C3A C2A H2AA 109.2 . . ?
C3A C2A H2AB 109.2 . . ?
N1A C3A C2A 108.6(8) . . ?
N1A C3A H3A 107.8 . . ?
N1A C3A C4A 110.0(8) . . ?
C2A C3A H3A 107.8 . . ?
C4A C3A C2A 114.6(8) . . ?
C4A C3A H3A 107.8 . . ?
C5A C4A C3A 120.1(12) . . ?
C5A C4A C9A 117.8(12) . . ?
C9A C4A C3A 122.0(10) . . ?
C4A C5A H5A 119.3 . . ?
C4A C5A C6A 121.4(16) . . ?
C6A C5A H5A 119.3 . . ?
C5A C6A H6A 121.2 . . ?
C5A C6A C7A 117.6(15) . . ?
C7A C6A H6A 121.2 . . ?
C6A C7A H7A 119.1 . . ?
C8A C7A C6A 121.9(14) . . ?
C8A C7A H7A 119.1 . . ?
C7A C8A H8A 121.0 . . ?
C7A C8A C9A 117.9(15) . . ?
C9A C8A H8A 121.0 . . ?
C4A C9A H9A 118.4 . . ?
C8A C9A C4A 123.2(14) . . ?
C8A C9A H9A 118.4 . . ?
H1BA N1B H1BB 109.5 . . ?
H1BA N1B H1BC 109.5 . . ?
H1BB N1B H1BC 109.5 . . ?
C3B N1B H1BA 109.5 . . ?
C3B N1B H1BB 109.5 . . ?
C3B N1B H1BC 109.5 . . ?
H1BD C1B H1BE 109.5 . . ?
H1BD C1B H1BF 109.5 . . ?
H1BE C1B H1BF 109.5 . . ?
C2B C1B H1BD 109.5 . . ?
C2B C1B H1BE 109.5 . . ?
C2B C1B H1BF 109.5 . . ?
C1B C2B H2BA 108.6 . . ?
C1B C2B H2BB 108.6 . . ?
H2BA C2B H2BB 107.6 . . ?
C3B C2B C1B 114.6(9) . . ?
C3B C2B H2BA 108.6 . . ?
C3B C2B H2BB 108.6 . . ?
N1B C3B H3B 108.0 . . ?
C2B C3B N1B 108.6(8) . . ?
C2B C3B H3B 108.0 . . ?
C4B C3B N1B 109.6(8) . . ?
C4B C3B C2B 114.4(8) . . ?
C4B C3B H3B 108.0 . . ?
C5B C4B C3B 118.3(10) . . ?
C5B C4B C9B 120.3(10) . . ?
C9B C4B C3B 121.3(10) . . ?
C4B C5B H5B 120.7 . . ?
C4B C5B C6B 118.6(11) . . ?
C6B C5B H5B 120.7 . . ?
C5B C6B H6B 119.6 . . ?
C7B C6B C5B 120.8(12) . . ?
C7B C6B H6B 119.6 . . ?
C6B C7B H7B 119.8 . . ?
C8B C7B C6B 120.4(11) . . ?
C8B C7B H7B 119.8 . . ?
C7B C8B H8B 119.7 . . ?
C7B C8B C9B 120.6(12) . . ?
C9B C8B H8B 119.7 . . ?
C4B C9B C8B 119.2(12) . . ?
C4B C9B H9B 120.4 . . ?
C8B C9B H9B 120.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1AA Br4 0.91 2.66 3.565(9) 176.6 4_566 yes
N1A H1AB Br1 0.91 2.73 3.413(9) 132.7 . yes
N1A H1AB Br2 0.91 2.74 3.500(9) 141.2 . yes
N1A H1AC Br1 0.91 2.94 3.760(8) 150.9 4_466 yes
N1B H1BA Br1 0.91 2.78 3.480(8) 134.2 1_455 yes
N1B H1BB Br3 0.91 2.67 3.549(9) 161.7 . yes
N1B H1BB Br6 0.91 2.96 3.430(8) 114.2 . yes
N1B H1BC Br5 0.91 2.64 3.514(8) 162.2 1_455 yes

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
N1A C3A C4A C5A 113.8(12) . . . . ?
N1A C3A C4A C9A -65.6(13) . . . . ?
C1A C2A C3A N1A -174.2(9) . . . . ?
C1A C2A C3A C4A 62.4(13) . . . . ?
C2A C3A C4A C5A -123.6(12) . . . . ?
C2A C3A C4A C9A 57.0(14) . . . . ?
C3A C4A C5A C6A 178.8(12) . . . . ?
C3A C4A C9A C8A -178.0(11) . . . . ?
C4A C5A C6A C7A 2(2) . . . . ?
C5A C4A C9A C8A 2.6(19) . . . . ?
C5A C6A C7A C8A -2(2) . . . . ?
C6A C7A C8A C9A 3(2) . . . . ?
C7A C8A C9A C4A -3(2) . . . . ?
C9A C4A C5A C6A -2(2) . . . . ?
N1B C3B C4B C5B 128.5(10) . . . . ?
N1B C3B C4B C9B -53.1(13) . . . . ?
C1B C2B C3B N1B -57.9(12) . . . . ?
C1B C2B C3B C4B 179.4(10) . . . . ?
C2B C3B C4B C5B -109.3(11) . . . . ?
C2B C3B C4B C9B 69.1(14) . . . . ?
C3B C4B C5B C6B 177.6(10) . . . . ?
C3B C4B C9B C8B -179.3(11) . . . . ?
C4B C5B C6B C7B 1.4(19) . . . . ?
C5B C4B C9B C8B -0.9(19) . . . . ?
C5B C6B C7B C8B 0(2) . . . . ?
C6B C7B C8B C9B -2(2) . . . . ?
C7B C8B C9B C4B 2(2) . . . . ?
C9B C4B C5B C6B -0.9(18) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop with paratone'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.942(13)
2 0.058(13)

_vrf_PLAT420_ceph024             
;
PROBLEM: D-H Bond Without Acceptor N1A --H1AC. Please Check
RESPONSE: H1AC acceptor atom is a symmetry generated Br1 atom
 located 2.9 A away.
;
####################################################################### 
# 
# 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_ceph061
_database_code_depnum_ccdc_archive 'CCDC 2359004'
loop_
_audit_author_name
_audit_author_address
'Chartrand '
;University of Montreal
Canada
;
_audit_update_record             
;
2024-05-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2023-09-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
daniel.chartrand.1@umontreal.ca
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I3 Sn, C9 H14 N'
_chemical_formula_sum            'C9 H14 I3 N Sn'
_chemical_formula_weight         635.60
_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 0.0148 0.0070 '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'
I I 0.0030 5.4350 '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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   8.2467(3)
_cell_length_b                   8.5854(3)
_cell_length_c                   21.7734(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1541.58(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7570
_cell_measurement_temperature    150
_cell_measurement_theta_max      59.905
_cell_measurement_theta_min      3.533
_shelx_estimated_absorpt_T_max   0.370
_shelx_estimated_absorpt_T_min   0.191
_exptl_absorpt_coefficient_mu    41.308
_exptl_absorpt_correction_T_max  0.1551
_exptl_absorpt_correction_T_min  0.0472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1531 before and 0.0763 after correction.
The Ratio of minimum to maximum transmission is 0.3043.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.739
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14645
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.575
_diffrn_reflns_theta_min         3.532
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1631
_reflns_number_total             1874
_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 (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_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         1.267
_refine_diff_density_min         -0.830
_refine_diff_density_rms         0.242
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1874
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0739P)²+5.2345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1246
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups
2. Restrained distances
 H1A-N1 = N1-H1B = H1C-N1
 0.91 with sigma of 0.02
 C8-C7 \\sim C7-C6 \\sim C5-C4 \\sim C4-C9 \\sim C9-C8 \\sim C5-C6
 with sigma of 0.02
 H1B-H1C \\sim H1C-H1A \\sim H1B-H1C \\sim H1A-H1B
 with sigma of 0.02
 H1B-C3 \\sim C3-H1C \\sim C3-H1A
 with sigma of 0.02
3. Others
 Fixed Sof: I2(0.5) N1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C1(0.5) H1D(0.5)
 H1E(0.5) H1F(0.5) C2(0.5) H2A(0.5) H2B(0.5) C3(0.5) H3(0.5) C4(0.5) C5(0.5)
 H5(0.5) C6(0.5) H6(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) H9(0.5)
4.a Ternary CH refined with riding coordinates:
 C3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
4.d Idealised Me refined as rotating group:
 C1(H1D,H1E,H1F)
;
_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
I2 I 0.15639(9) 1.21956(10) 0.63703(3) 0.0360(4) Uani 0.5 1 d . . P A -1
I1 I 0.56002(6) 0.99069(5) 0.70376(2) 0.0440(2) Uani 1 1 d . . . . .
Sn1 Sn 0.34521(8) 1.250000 0.75313(3) 0.0345(2) Uani 1 2 d S T P . .
N1 N 0.2065(14) 0.7836(11) 0.6649(4) 0.036(4) Uani 0.5 1 d D . P B -1
H1A H 0.308(6) 0.754(13) 0.677(4) 0.054 Uiso 0.5 1 d D U P C -1
H1B H 0.231(12) 0.887(4) 0.660(5) 0.054 Uiso 0.5 1 d D U P D -1
H1C H 0.164(12) 0.794(11) 0.703(2) 0.054 Uiso 0.5 1 d D U P E -1
C1 C -0.1540(19) 0.666(3) 0.5669(9) 0.068(5) Uani 0.5 1 d . . P B -1
H1D H -0.128287 0.711673 0.526878 0.103 Uiso 0.5 1 calc R U P B -1
H1E H -0.269655 0.679947 0.575651 0.103 Uiso 0.5 1 calc R U P B -1
H1F H -0.128299 0.554435 0.566352 0.103 Uiso 0.5 1 calc R U P B -1
C2 C -0.0566(15) 0.744(8) 0.6153(6) 0.055(5) Uani 0.5 1 d . . P B -1
H2A H -0.104233 0.719492 0.655931 0.066 Uiso 0.5 1 calc R U P B -1
H2B H -0.063530 0.858121 0.609383 0.066 Uiso 0.5 1 calc R U P B -1
C3 C 0.1195(18) 0.6965(16) 0.6154(6) 0.042(3) Uani 0.5 1 d D . P B -1
H3 H 0.125939 0.582630 0.624838 0.050 Uiso 0.5 1 calc R U P B -1
C4 C 0.2155(15) 0.728(2) 0.5562(6) 0.041(5) Uani 0.5 1 d D . P B -1
C5 C 0.3288(19) 0.6183(17) 0.5396(6) 0.052(4) Uani 0.5 1 d D . P B -1
H5 H 0.347872 0.530415 0.565119 0.062 Uiso 0.5 1 calc R U P B -1
C6 C 0.4156(18) 0.6368(18) 0.4852(6) 0.045(3) Uani 0.5 1 d D . P B -1
H6 H 0.492763 0.560123 0.473502 0.054 Uiso 0.5 1 calc R U P B -1
C7 C 0.3910(16) 0.766(3) 0.4479(6) 0.043(3) Uani 0.5 1 d D . P B -1
H7 H 0.452226 0.779099 0.411293 0.052 Uiso 0.5 1 calc R U P B -1
C8 C 0.2750(17) 0.8747(16) 0.4650(6) 0.045(3) Uani 0.5 1 d D . P B -1
H8 H 0.255118 0.962685 0.439616 0.054 Uiso 0.5 1 calc R U P B -1
C9 C 0.1876(17) 0.8556(18) 0.5193(6) 0.046(3) Uani 0.5 1 d D . P B -1
H9 H 0.108835 0.930792 0.530935 0.055 Uiso 0.5 1 calc R U P B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 Sn1 2.9804(10) . ?
I1 Sn1 3.0414(6) . ?
N1 H1A 0.91(2) . ?
N1 H1B 0.92(2) . ?
N1 H1C 0.91(2) . ?
N1 C3 1.496(17) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C1 C2 1.48(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.51(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.537(18) . ?
C4 C5 1.373(13) . ?
C4 C9 1.380(14) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(12) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(14) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(13) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(12) . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I2 Sn1 I1 86.58(2) . . ?
I2 Sn1 I1 93.94(2) . 7_585 ?
I1 Sn1 I1 94.11(3) . 7_585 ?
H1A N1 H1B 96(8) . . ?
H1A N1 H1C 97(8) . . ?
H1B N1 H1C 96(8) . . ?
C3 N1 H1A 121(7) . . ?
C3 N1 H1B 120(6) . . ?
C3 N1 H1C 122(7) . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C1 C2 C3 114(3) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
N1 C3 C2 109(2) . . ?
N1 C3 H3 108.4 . . ?
N1 C3 C4 105.7(11) . . ?
C2 C3 H3 108.4 . . ?
C2 C3 C4 116.6(13) . . ?
C4 C3 H3 108.4 . . ?
C5 C4 C3 116.8(13) . . ?
C5 C4 C9 120.3(12) . . ?
C9 C4 C3 122.8(12) . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.7(13) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.9(13) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.7(12) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.3(12) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 120.1(13) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A I1 0.91(2) 2.96(10) 3.518(11) 121(9) . yes
N1 H1A I1 0.91(2) 3.02(6) 3.842(10) 152(9) 7_575 yes
N1 H1B I2 0.92(2) 2.96(5) 3.814(10) 155(8) . yes
N1 H1C I1 0.91(2) 3.29(8) 3.896(10) 127(7) 4_466 yes
N1 H1C I1 0.91(2) 2.78(5) 3.577(10) 148(8) 6_557 yes

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
N1 C3 C4 C5 95.6(17) . . . . ?
N1 C3 C4 C9 -86.8(17) . . . . ?
C1 C2 C3 N1 179(3) . . . . ?
C1 C2 C3 C4 59(4) . . . . ?
C2 C3 C4 C5 -143(3) . . . . ?
C2 C3 C4 C9 35(3) . . . . ?
C3 C4 C5 C6 177.6(13) . . . . ?
C3 C4 C9 C8 -177.8(14) . . . . ?
C4 C5 C6 C7 1(3) . . . . ?
C5 C4 C9 C8 0(2) . . . . ?
C5 C6 C7 C8 -1(3) . . . . ?
C6 C7 C8 C9 1(3) . . . . ?
C7 C8 C9 C4 0(2) . . . . ?
C9 C4 C5 C6 0(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop with paratone'
_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT420_ceph061             
;
PROBLEM: D-H Bond Without Acceptor N1 --H1C Please Check
RESPONSE: H1C acceptor atom is the I2 atom, located at 3.3 A away. 
;
####################################################################### 
# 
# 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_ceph051
_database_code_depnum_ccdc_archive 'CCDC 2359002'
loop_
_audit_author_name
_audit_author_address
'Chartrand '
;University of Montreal
Canada
;
_audit_update_record             
;
2024-05-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2023-09-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(I3 Sn), 2(C9 H14 N)'
_chemical_formula_sum            'C18 H28 I6 N2 Sn2'
_chemical_formula_weight         1271.20
_chemical_absolute_configuration ad
_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'
I I 0.0030 5.4350 '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 0.1615 4.3612 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5559(2)
_cell_length_b                   8.6602(2)
_cell_length_c                   20.3328(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1506.58(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    150
_cell_measurement_theta_max      62.364
_cell_measurement_theta_min      4.830
_shelx_estimated_absorpt_T_max   0.365
_shelx_estimated_absorpt_T_min   0.122
_exptl_absorpt_coefficient_mu    42.125
_exptl_absorpt_correction_T_max  0.1244
_exptl_absorpt_correction_T_min  0.0161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1545 before and 0.0816 after correction.
The Ratio of minimum to maximum transmission is 0.1294.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.802
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.086
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15515
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         62.335
_diffrn_reflns_theta_min         3.783
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                3399
_reflns_number_total             3432
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_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         1.328
_refine_diff_density_min         -1.696
_refine_diff_density_rms         0.292
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+2.0067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0684
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.90(3)
 0.10(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups
3. Restrained distances
 H1C-N1 = N1-H1B = N1-H1A
 0.91 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
4.d Idealised Me refined as rotating group:
 C1(H1D,H1E,H1F)
;
_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
I1 I 0.05228(5) 0.50869(5) 0.53804(2) 0.02810(12) Uani 1 1 d . . . . .
I2 I 0.44937(6) 0.28786(5) 0.61848(2) 0.02855(13) Uani 1 1 d . . . . .
I3 I 0.08656(5) -0.00302(5) 0.55154(2) 0.02795(12) Uani 1 1 d . . . . .
Sn1 Sn 0.27805(5) 0.24778(6) 0.49409(2) 0.02695(13) Uani 1 1 d . . . . .
N1 N 0.3983(8) 0.7167(9) 0.5905(3) 0.0306(13) Uani 1 1 d D . . . .
H1A H 0.299(5) 0.745(12) 0.581(5) 0.046 Uiso 1 1 d D U . . .
H1B H 0.392(13) 0.613(4) 0.597(5) 0.046 Uiso 1 1 d D U . . .
H1C H 0.449(12) 0.730(12) 0.551(3) 0.046 Uiso 1 1 d D U . . .
C1 C 0.7340(10) 0.7794(12) 0.6253(4) 0.043(2) Uani 1 1 d . . . . .
H1D H 0.834948 0.761902 0.646755 0.064 Uiso 1 1 calc R U . . .
H1E H 0.728906 0.885913 0.609154 0.064 Uiso 1 1 calc R U . . .
H1F H 0.722525 0.707897 0.588207 0.064 Uiso 1 1 calc R U . . .
C2 C 0.6023(9) 0.7520(10) 0.6746(4) 0.0330(16) Uani 1 1 d . . . . .
H2A H 0.596755 0.640118 0.684350 0.040 Uiso 1 1 calc R U . . .
H2B H 0.628575 0.805920 0.716083 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4421(10) 0.8061(9) 0.6517(3) 0.0290(15) Uani 1 1 d . . . . .
H3 H 0.450301 0.917771 0.639623 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3167(9) 0.7901(10) 0.7040(3) 0.0279(15) Uani 1 1 d . . . . .
C5 C 0.2497(10) 0.9209(9) 0.7305(4) 0.0295(15) Uani 1 1 d . . . . .
H5 H 0.279000 1.019737 0.714424 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1394(12) 0.9094(11) 0.7808(4) 0.040(2) Uani 1 1 d . . . . .
H6 H 0.094013 0.999904 0.799027 0.047 Uiso 1 1 calc R U . . .
C7 C 0.0962(11) 0.7646(11) 0.8040(4) 0.0388(19) Uani 1 1 d . . . . .
H7 H 0.021283 0.755623 0.838221 0.047 Uiso 1 1 calc R U . . .
C8 C 0.1623(12) 0.6347(12) 0.7772(4) 0.041(2) Uani 1 1 d . . . . .
H8 H 0.131033 0.535926 0.792677 0.049 Uiso 1 1 calc R U . . .
C9 C 0.2748(11) 0.6448(11) 0.7275(4) 0.0369(18) Uani 1 1 d . . . . .
H9 H 0.321763 0.554218 0.710056 0.044 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
I1 Sn1 3.1042(7) . ?
I2 Sn1 2.9439(6) . ?
I3 Sn1 2.9607(7) . ?
N1 H1A 0.90(3) . ?
N1 H1B 0.91(3) . ?
N1 H1C 0.91(3) . ?
N1 C3 1.513(9) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C1 C2 1.527(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.522(11) . ?
C3 H3 1.0000 . ?
C3 C4 1.516(10) . ?
C4 C5 1.380(11) . ?
C4 C9 1.393(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(12) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(14) . ?
C7 H7 0.9500 . ?
C7 C8 1.372(14) . ?
C8 H8 0.9500 . ?
C8 C9 1.398(12) . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I2 Sn1 I1 88.663(18) . . ?
I2 Sn1 I3 91.321(18) . . ?
I3 Sn1 I1 94.362(18) . . ?
H1A N1 H1B 104(10) . . ?
H1A N1 H1C 103(10) . . ?
H1B N1 H1C 107(9) . . ?
C3 N1 H1A 106(7) . . ?
C3 N1 H1B 113(7) . . ?
C3 N1 H1C 122(7) . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 C1 114.6(6) . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
N1 C3 C2 108.5(6) . . ?
N1 C3 H3 108.1 . . ?
N1 C3 C4 110.7(6) . . ?
C2 C3 H3 108.1 . . ?
C4 C3 C2 113.3(6) . . ?
C4 C3 H3 108.1 . . ?
C5 C4 C3 119.6(7) . . ?
C5 C4 C9 120.0(7) . . ?
C9 C4 C3 120.4(7) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(8) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.5(8) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.7(8) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.3(9) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C8 118.8(8) . . ?
C4 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?

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
N1 H1A I1 0.90(3) 3.06(9) 3.626(7) 122(8) . yes
N1 H1A I3 0.90(3) 2.91(6) 3.692(7) 146(8) 1_565 yes
N1 H1B I2 0.91(3) 2.89(4) 3.782(8) 167(10) . yes
N1 H1C I1 0.91(3) 3.03(7) 3.772(7) 139(8) 4_566 yes
N1 H1C I3 0.91(3) 3.11(8) 3.790(7) 133(8) 4_556 yes

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
N1 C3 C4 C5 -124.8(8) . . . . ?
N1 C3 C4 C9 58.4(9) . . . . ?
C1 C2 C3 N1 61.6(9) . . . . ?
C1 C2 C3 C4 -175.0(7) . . . . ?
C2 C3 C4 C5 113.0(8) . . . . ?
C2 C3 C4 C9 -63.7(10) . . . . ?
C3 C4 C5 C6 -177.0(7) . . . . ?
C3 C4 C9 C8 178.0(8) . . . . ?
C4 C5 C6 C7 -0.3(13) . . . . ?
C5 C4 C9 C8 1.2(12) . . . . ?
C5 C6 C7 C8 -0.1(13) . . . . ?
C6 C7 C8 C9 1.1(14) . . . . ?
C7 C8 C9 C4 -1.6(14) . . . . ?
C9 C4 C5 C6 -0.2(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.90(3)
2 0.10(3)

####################################################################### 
# 
# 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_ceph011
_database_code_depnum_ccdc_archive 'CCDC 2359001'
loop_
_audit_author_name
_audit_author_address
'Chartrand '
;University of Montreal
Canada
;
_audit_update_record             
;
2024-05-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2023-09-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
daniel.chartrand.1@umontreal.ca
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br6 Sn, 2(C9 H14 N)'
_chemical_formula_sum            'C18 H28 Br6 N2 Sn'
_chemical_formula_weight         870.57
_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.5056(4)
_cell_length_b                   13.0933(8)
_cell_length_c                   27.1689(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2670.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    150
_cell_measurement_theta_max      57.386
_cell_measurement_theta_min      2.831
_shelx_estimated_absorpt_T_max   0.527
_shelx_estimated_absorpt_T_min   0.322
_exptl_absorpt_coefficient_mu    12.225
_exptl_absorpt_correction_T_max  0.1512
_exptl_absorpt_correction_T_min  0.0417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1443 before and 0.0747 after correction.
The Ratio of minimum to maximum transmission is 0.2758.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.166
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            21046
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         58.202
_diffrn_reflns_theta_min         5.667
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2198
_reflns_number_total             2685
_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 (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_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         0.900
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0153P)²+19.1397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0889
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1A \\sim N1-H1B \\sim N1-H1C
 with sigma of 0.02
 H1A-H1B \\sim H1B-H1C \\sim H1C-H1A
 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C5(H5), C8(H8), C7(H7)
3.d Idealised Me refined as rotating group:
 C1(H1D,H1E,H1F)
;
_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 1.000000 0.500000 0.500000 0.03712(16) Uani 1 2 d S . P . .
Br1 Br 0.78597(8) 0.36769(5) 0.53913(2) 0.04117(17) Uani 1 1 d . . . . .
Br2 Br 0.72323(9) 0.59690(5) 0.46638(2) 0.04332(18) Uani 1 1 d . . . . .
Br3 Br 0.99143(9) 0.60948(6) 0.57983(3) 0.04616(19) Uani 1 1 d . . . . .
N1 N 0.4344(8) 0.6703(4) 0.5686(2) 0.0429(12) Uani 1 1 d D . . . .
H1A H 0.503(7) 0.637(3) 0.548(2) 0.052 Uiso 1 1 d D U . . .
H1B H 0.428(7) 0.735(3) 0.559(2) 0.052 Uiso 1 1 d D U . . .
H1C H 0.325(5) 0.645(4) 0.567(2) 0.052 Uiso 1 1 d D U . . .
C6 C 0.3804(9) 0.9003(6) 0.6903(2) 0.0504(17) Uani 1 1 d . . . . .
H6 H 0.420699 0.968608 0.694310 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5211(9) 0.6650(5) 0.6186(2) 0.0453(15) Uani 1 1 d . . . . .
H3 H 0.643856 0.693810 0.615240 0.054 Uiso 1 1 calc R U . . .
C9 C 0.2653(10) 0.7024(6) 0.6782(2) 0.0527(17) Uani 1 1 d . . . . .
H9 H 0.224686 0.634193 0.674089 0.063 Uiso 1 1 calc R U . . .
C2 C 0.5401(10) 0.5563(6) 0.6340(3) 0.0527(17) Uani 1 1 d . . . . .
H2A H 0.605248 0.518431 0.608111 0.063 Uiso 1 1 calc R U . . .
H2B H 0.420211 0.525477 0.637168 0.063 Uiso 1 1 calc R U . . .
C1 C 0.6384(10) 0.5450(6) 0.6824(3) 0.061(2) Uani 1 1 d . . . . .
H1D H 0.754922 0.578384 0.680025 0.091 Uiso 1 1 calc R U . . .
H1E H 0.654966 0.472322 0.689744 0.091 Uiso 1 1 calc R U . . .
H1F H 0.568853 0.576926 0.708779 0.091 Uiso 1 1 calc R U . . .
C5 C 0.4731(9) 0.8344(5) 0.6600(2) 0.0460(15) Uani 1 1 d . . . . .
H5 H 0.576904 0.857875 0.643458 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4176(9) 0.7355(5) 0.6532(2) 0.0431(15) Uani 1 1 d . . . . .
C8 C 0.1733(10) 0.7683(6) 0.7088(3) 0.0570(19) Uani 1 1 d . . . . .
H8 H 0.070525 0.744785 0.725807 0.068 Uiso 1 1 calc R U . . .
C7 C 0.2294(9) 0.8677(6) 0.7150(2) 0.0541(18) Uani 1 1 d . . . . .
H7 H 0.165599 0.913021 0.735855 0.065 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 Br1 2.5908(6) 5_766 ?
Sn1 Br1 2.5908(6) . ?
Sn1 Br2 2.5999(6) . ?
Sn1 Br2 2.5999(6) 5_766 ?
Sn1 Br3 2.6006(7) . ?
Sn1 Br3 2.6007(7) 5_766 ?
N1 H1A 0.88(3) . ?
N1 H1B 0.89(3) . ?
N1 H1C 0.89(3) . ?
N1 C3 1.509(8) . ?
C6 H6 0.9500 . ?
C6 C5 1.382(9) . ?
C6 C7 1.385(10) . ?
C3 H3 1.0000 . ?
C3 C2 1.490(10) . ?
C3 C4 1.530(9) . ?
C9 H9 0.9500 . ?
C9 C4 1.398(10) . ?
C9 C8 1.384(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.515(9) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C5 H5 0.9500 . ?
C5 C4 1.372(9) . ?
C8 H8 0.9500 . ?
C8 C7 1.378(10) . ?
C7 H7 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Sn1 Br1 180.0 5_766 . ?
Br1 Sn1 Br2 91.43(2) 5_766 . ?
Br1 Sn1 Br2 88.57(2) . . ?
Br1 Sn1 Br2 88.57(2) 5_766 5_766 ?
Br1 Sn1 Br2 91.43(2) . 5_766 ?
Br1 Sn1 Br3 89.37(2) 5_766 . ?
Br1 Sn1 Br3 89.37(2) . 5_766 ?
Br1 Sn1 Br3 90.63(2) . . ?
Br1 Sn1 Br3 90.63(2) 5_766 5_766 ?
Br2 Sn1 Br2 180.00(3) . 5_766 ?
Br2 Sn1 Br3 90.25(2) 5_766 5_766 ?
Br2 Sn1 Br3 89.75(2) 5_766 . ?
Br2 Sn1 Br3 90.25(2) . . ?
Br2 Sn1 Br3 89.75(2) . 5_766 ?
Br3 Sn1 Br3 180.00(3) . 5_766 ?
H1A N1 H1B 109(3) . . ?
H1A N1 H1C 109(3) . . ?
H1B N1 H1C 107(3) . . ?
C3 N1 H1A 108(4) . . ?
C3 N1 H1B 109(4) . . ?
C3 N1 H1C 115(4) . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.6(7) . . ?
C7 C6 H6 119.7 . . ?
N1 C3 H3 107.3 . . ?
N1 C3 C4 107.9(5) . . ?
C2 C3 N1 109.7(5) . . ?
C2 C3 H3 107.3 . . ?
C2 C3 C4 116.9(6) . . ?
C4 C3 H3 107.3 . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C4 120.4(7) . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C3 C2 C1 112.6(6) . . ?
H2A C2 H2B 107.8 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(6) . . ?
C4 C5 H5 119.5 . . ?
C9 C4 C3 121.7(6) . . ?
C5 C4 C3 119.8(6) . . ?
C5 C4 C9 118.5(6) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.7(7) . . ?
C7 C8 H8 119.7 . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 118.9(7) . . ?
C8 C7 H7 120.6 . . ?

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
N1 H1A Br2 0.88(3) 2.81(4) 3.652(5) 161(5) . yes
N1 H1B Br1 0.89(3) 2.82(5) 3.424(5) 127(4) 8_765 yes
N1 H1B Br2 0.89(3) 2.77(4) 3.564(6) 150(4) 4_466 yes
N1 H1C Br3 0.89(3) 2.57(4) 3.432(6) 164(5) 1_455 yes

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
N1 C3 C2 C1 175.9(5) . . . . ?
N1 C3 C4 C9 85.5(7) . . . . ?
N1 C3 C4 C5 -93.8(7) . . . . ?
C6 C5 C4 C3 178.9(6) . . . . ?
C6 C5 C4 C9 -0.5(10) . . . . ?
C9 C8 C7 C6 -0.5(11) . . . . ?
C2 C3 C4 C9 -38.7(9) . . . . ?
C2 C3 C4 C5 142.0(7) . . . . ?
C5 C6 C7 C8 0.1(10) . . . . ?
C4 C3 C2 C1 -60.9(8) . . . . ?
C4 C9 C8 C7 0.5(11) . . . . ?
C8 C9 C4 C3 -179.3(6) . . . . ?
C8 C9 C4 C5 0.1(10) . . . . ?
C7 C6 C5 C4 0.4(10) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop with paratone'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ceph041
_database_code_depnum_ccdc_archive 'CCDC 2359003'
loop_
_audit_author_name
_audit_author_address
'Chartrand D.'
;University of Montreal
Canada
;
_audit_update_record             
;
2024-05-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2023-09-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
daniel.chartrand.1@umontreal.ca
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I3 Sn, C9 H14 N'
_chemical_formula_sum            'C9 H14 I3 N Sn'
_chemical_formula_weight         635.60
_chemical_absolute_configuration ad
_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'
I I 0.0030 5.4350 '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 0.1615 4.3612 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5537(4)
_cell_length_b                   8.6479(3)
_cell_length_c                   20.3305(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1503.88(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6552
_cell_measurement_temperature    150
_cell_measurement_theta_max      63.837
_cell_measurement_theta_min      3.784
_shelx_estimated_absorpt_T_max   0.364
_shelx_estimated_absorpt_T_min   0.122
_exptl_absorpt_coefficient_mu    42.201
_exptl_absorpt_correction_T_max  0.0889
_exptl_absorpt_correction_T_min  0.0100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1472 before and 0.0589 after correction.
The Ratio of minimum to maximum transmission is 0.1125.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.807
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.086
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9623
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         63.979
_diffrn_reflns_theta_min         3.783
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                3175
_reflns_number_total             3534
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_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         1.483
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.265
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3534
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      0.998
_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)+(0.0495P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0893
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.97(3)
 0.03(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups
3. Restrained distances
 H1C-N1 = N1-H1B = N1-H1A
 0.91 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
4.d Idealised Me refined as rotating group:
 C1(H1D,H1E,H1F)
;
_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
I1 I 0.94786(8) 0.49132(7) 0.46193(3) 0.03990(18) Uani 1 1 d . . . . .
I2 I 0.55066(9) 0.71222(7) 0.38151(3) 0.04088(18) Uani 1 1 d . . . . .
I3 I 0.91341(8) 1.00300(8) 0.44843(3) 0.03983(18) Uani 1 1 d . . . . .
Sn1 Sn 0.72199(8) 0.75228(8) 0.50591(4) 0.03876(18) Uani 1 1 d . . . . .
N1 N 0.6014(13) 0.2825(12) 0.4089(5) 0.044(2) Uani 1 1 d D . . . .
H1A H 0.701(7) 0.252(15) 0.418(7) 0.066 Uiso 1 1 d D U . . .
H1B H 0.602(17) 0.387(4) 0.402(7) 0.066 Uiso 1 1 d D U . . .
H1C H 0.527(13) 0.286(16) 0.441(5) 0.066 Uiso 1 1 d D U . . .
C1 C 0.2682(15) 0.2208(16) 0.3741(7) 0.056(3) Uani 1 1 d . . . . .
H1D H 0.167216 0.240691 0.352906 0.084 Uiso 1 1 calc R U . . .
H1E H 0.281415 0.291208 0.411438 0.084 Uiso 1 1 calc R U . . .
H1F H 0.271459 0.113639 0.389675 0.084 Uiso 1 1 calc R U . . .
C2 C 0.3977(13) 0.2467(14) 0.3253(6) 0.045(2) Uani 1 1 d . . . . .
H2A H 0.371099 0.192058 0.284011 0.054 Uiso 1 1 calc R U . . .
H2B H 0.403350 0.358585 0.315190 0.054 Uiso 1 1 calc R U . . .
C3 C 0.5558(14) 0.1935(12) 0.3478(5) 0.042(2) Uani 1 1 d . . . . .
H3 H 0.547745 0.081622 0.359880 0.050 Uiso 1 1 calc R U . . .
C4 C 0.6847(13) 0.2103(13) 0.2962(5) 0.039(2) Uani 1 1 d . . . . .
C5 C 0.7513(15) 0.0812(13) 0.2697(5) 0.044(3) Uani 1 1 d . . . . .
H5 H 0.722953 -0.017637 0.286248 0.053 Uiso 1 1 calc R U . . .
C6 C 0.8602(18) 0.0913(17) 0.2188(6) 0.056(3) Uani 1 1 d . . . . .
H6 H 0.903901 0.000421 0.200122 0.067 Uiso 1 1 calc R U . . .
C7 C 0.9031(14) 0.2339(15) 0.1964(6) 0.049(3) Uani 1 1 d . . . . .
H7 H 0.979247 0.243108 0.162607 0.059 Uiso 1 1 calc R U . . .
C8 C 0.8352(17) 0.3650(16) 0.2231(6) 0.053(3) Uani 1 1 d . . . . .
H8 H 0.865166 0.463911 0.207135 0.063 Uiso 1 1 calc R U . . .
C9 C 0.7247(16) 0.3551(14) 0.2726(5) 0.047(3) Uani 1 1 d . . . . .
H9 H 0.677412 0.445586 0.290091 0.056 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
I1 Sn1 3.1024(10) . ?
I2 Sn1 2.9434(10) . ?
I3 Sn1 2.9576(10) . ?
N1 H1A 0.92(3) . ?
N1 H1B 0.91(3) . ?
N1 H1C 0.91(3) . ?
N1 C3 1.511(15) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C1 C2 1.503(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.501(15) . ?
C3 H3 1.0000 . ?
C3 C4 1.530(16) . ?
C4 C5 1.364(16) . ?
C4 C9 1.383(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.365(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(17) . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I2 Sn1 I1 88.67(3) . . ?
I2 Sn1 I3 91.29(3) . . ?
I3 Sn1 I1 94.28(3) . . ?
H1A N1 H1B 109(10) . . ?
H1A N1 H1C 121(10) . . ?
H1B N1 H1C 95(10) . . ?
C3 N1 H1A 105(9) . . ?
C3 N1 H1B 112(9) . . ?
C3 N1 H1C 115(9) . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 C1 114.6(10) . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
N1 C3 H3 108.0 . . ?
N1 C3 C4 109.2(9) . . ?
C2 C3 N1 109.1(10) . . ?
C2 C3 H3 108.0 . . ?
C2 C3 C4 114.2(9) . . ?
C4 C3 H3 108.0 . . ?
C5 C4 C3 119.6(10) . . ?
C5 C4 C9 120.1(10) . . ?
C9 C4 C3 120.1(10) . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.3(11) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.0(12) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.7(12) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(12) . . ?
C9 C8 H8 119.3 . . ?
C4 C9 H9 120.8 . . ?
C8 C9 C4 118.5(12) . . ?
C8 C9 H9 120.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A I1 0.92(3) 3.09(12) 3.634(10) 120(10) . yes
N1 H1A I3 0.92(3) 2.88(8) 3.689(11) 148(11) 1_545 yes
N1 H1B I2 0.91(3) 2.88(4) 3.783(10) 171(13) . yes
N1 H1C I1 0.91(3) 3.18(12) 3.773(10) 125(11) 4_456 yes
N1 H1C I3 0.91(3) 3.05(9) 3.801(10) 140(11) 4_466 yes

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
N1 C3 C4 C5 124.9(11) . . . . ?
N1 C3 C4 C9 -60.1(13) . . . . ?
C1 C2 C3 N1 -61.4(13) . . . . ?
C1 C2 C3 C4 176.1(10) . . . . ?
C2 C3 C4 C5 -112.6(12) . . . . ?
C2 C3 C4 C9 62.3(14) . . . . ?
C3 C4 C5 C6 174.9(11) . . . . ?
C3 C4 C9 C8 -176.2(11) . . . . ?
C4 C5 C6 C7 1.5(19) . . . . ?
C5 C4 C9 C8 -1.3(17) . . . . ?
C5 C6 C7 C8 -1.7(19) . . . . ?
C6 C7 C8 C9 0.3(19) . . . . ?
C7 C8 C9 C4 1.2(19) . . . . ?
C9 C4 C5 C6 0.0(18) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop with paratone'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.97(3)
2 0.03(3)

