# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ortho_300k_103s_0p8
_database_code_depnum_ccdc_archive 'CCDC 2255223'
loop_
_audit_author_name
_audit_author_address
'Ethan Crace'
;Duke University
United States of America
;
_audit_update_record             
;
2023-04-10 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;
_audit_creation_date             2023-01-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'catena-[bis(heptan-2-ammonium) bis(mu-iodo)-diiodo-tin]'
_chemical_formula_moiety         'I4 Sn, 2(C7 H18 N)'
_chemical_formula_sum            'C14 H36 I4 N2 Sn'
_chemical_formula_weight         858.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 N2 Sn1 I4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           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                   9.2171(4)
_cell_length_b                   8.5923(4)
_cell_length_c                   34.0460(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2696.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5429
_cell_measurement_temperature    299.97(10)
_cell_measurement_theta_max      27.4740
_cell_measurement_theta_min      2.4000
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.294
_exptl_absorpt_coefficient_mu    5.526
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.727
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.115
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 12 -2 0.1094
13 0 5 0.0299
-12 -3 -4 0.0430
-9 -9 -3 0.1057
-11 6 -5 0.0649
1 0 -48 0.0010
-1 0 48 0.0084

_exptl_crystal_preparation       
'Crystals were grown by slow cooling tin (II) iodide and racemic 2-aminoheptane in hydroiodic acid with hypophosphorous acid as stabilizer. Samples were left sealed until use.'
_exptl_crystal_recrystallization_method 'See preparation details.'
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.009
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9019 11.9773 -1.8625 -0.0086 0.0030 1.0000
12.9214 0.4270 4.7398 0.2321 0.9659 -0.1151
-12.3961 -3.4562 -4.3499 -0.2312 -0.9630 -0.1382
-8.8258 -8.8630 -2.6827 -0.1824 -0.7623 -0.6210
-11.4371 5.6361 -4.5846 -0.1887 -0.7829 0.5928
1.3060 -0.2976 -47.7368 -0.9723 0.2335 -0.0091
-1.3060 0.2976 47.7368 0.9723 -0.2335 0.0091

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            25770
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.393
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.97(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  70.20   0.80  102.54    --    4.40  11.00 -20.00   99
  2  ω    -23.00  27.40   0.80  102.54    --   -5.65 -99.00 -60.00   63
  3  ω    -69.00  19.00   0.80  102.54    --    4.40 -11.00 166.00  110
  4  ω    -28.00  66.40   0.80  102.54    --   -5.65  77.00 -30.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0102617000
_diffrn_orient_matrix_UB_12      0.0041197000
_diffrn_orient_matrix_UB_13      0.0206232000
_diffrn_orient_matrix_UB_21      0.0754237000
_diffrn_orient_matrix_UB_22      0.0117787000
_diffrn_orient_matrix_UB_23      -0.0029018000
_diffrn_orient_matrix_UB_31      -0.0113736000
_diffrn_orient_matrix_UB_32      0.0815838000
_diffrn_orient_matrix_UB_33      -0.0006301000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2073
_reflns_number_total             2766
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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         1.258
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.357
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0843
_refine_ls_restrained_S_all      1.347
_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)+(0.0100P)²+54.5525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1583
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C9-C1 = C5-C1
 1.54 with sigma of 0.02
2. Rigid bond restraints
 C1, N004, C005, C006, C007, C6, C5, C9
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
N004 \\sim C005 \\sim C006 \\sim C007 \\sim C6 \\sim C5 \\sim C1 \\sim C9:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4.a Ternary CH refined with riding coordinates:
 C005(H005)
4.b Secondary CH2 refined with riding coordinates:
 C007(H00G,H00H), C5(H5A,H5B), C6(H6A,H6B), C1(H1A,H1B)
4.c Idealised Me refined as rotating group:
 N004(H00A,H00B,H00C), C006(H00D,H00E,H00F), C9(H9A,H9B,H9C)
;
_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
Sn00 Sn 0.500000 0.000000 0.500000 0.0503(4) Uani 1 2 d S . P . .
I002 I 0.30152(11) 0.30568(12) 0.50207(3) 0.0601(3) Uani 1 1 d . . . . .
I003 I 0.52646(12) 0.00948(15) 0.59241(3) 0.0672(4) Uani 1 1 d . . . . .
N004 N 0.5921(16) 0.4197(18) 0.5768(4) 0.077(4) Uani 1 1 d . U . . .
H00A H 0.559050 0.458034 0.554223 0.093 Uiso 1 1 calc R U . . .
H00B H 0.556066 0.324763 0.580498 0.093 Uiso 1 1 calc R U . . .
H00C H 0.688493 0.414857 0.576029 0.093 Uiso 1 1 calc R U . . .
C005 C 0.546(2) 0.523(2) 0.6097(6) 0.083(5) Uani 1 1 d . U . . .
H005 H 0.600412 0.620295 0.606946 0.099 Uiso 1 1 calc R U . . .
C006 C 0.394(2) 0.560(3) 0.6047(7) 0.109(8) Uani 1 1 d . U . . .
H00D H 0.380036 0.613112 0.580177 0.164 Uiso 1 1 calc R U . . .
H00E H 0.362160 0.625207 0.625866 0.164 Uiso 1 1 calc R U . . .
H00F H 0.337924 0.465349 0.604664 0.164 Uiso 1 1 calc R U . . .
C007 C 0.587(2) 0.454(3) 0.6485(6) 0.098(6) Uani 1 1 d . U . . .
H00G H 0.524384 0.365498 0.653448 0.117 Uiso 1 1 calc R U . . .
H00H H 0.685669 0.413969 0.646420 0.117 Uiso 1 1 calc R U . . .
C5 C 0.629(3) 0.472(4) 0.7193(7) 0.147(9) Uani 1 1 d D U . . .
H5A H 0.573806 0.376339 0.722360 0.176 Uiso 1 1 calc R U . . .
H5B H 0.730593 0.444971 0.717349 0.176 Uiso 1 1 calc R U . . .
C6 C 0.581(3) 0.554(3) 0.6818(7) 0.130(8) Uani 1 1 d . U . . .
H6A H 0.482559 0.591411 0.685066 0.156 Uiso 1 1 calc R U . . .
H6B H 0.643203 0.643348 0.677365 0.156 Uiso 1 1 calc R U . . .
C9 C 0.636(4) 0.496(4) 0.7931(7) 0.190(15) Uani 1 1 d D U . . .
H9A H 0.620975 0.385604 0.790473 0.285 Uiso 1 1 calc R U . . .
H9B H 0.572877 0.536175 0.812982 0.285 Uiso 1 1 calc R U . . .
H9C H 0.735343 0.514695 0.800481 0.285 Uiso 1 1 calc R U . . .
C1 C 0.605(4) 0.575(4) 0.7545(7) 0.188(12) Uani 1 1 d D U . . .
H1A H 0.666584 0.665635 0.752215 0.226 Uiso 1 1 calc R U . . .
H1B H 0.505024 0.609931 0.754596 0.226 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
Sn00 I002 3.2016(10) . ?
Sn00 I002 3.2016(10) 5_656 ?
Sn00 I003 3.1565(12) 5_656 ?
Sn00 I003 3.1566(12) . ?
N004 H00A 0.8900 . ?
N004 H00B 0.8900 . ?
N004 H00C 0.8900 . ?
N004 C005 1.49(2) . ?
C005 H005 0.9800 . ?
C005 C006 1.45(2) . ?
C005 C007 1.50(3) . ?
C006 H00D 0.9600 . ?
C006 H00E 0.9600 . ?
C006 H00F 0.9600 . ?
C007 H00G 0.9700 . ?
C007 H00H 0.9700 . ?
C007 C6 1.43(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.52(3) . ?
C5 C1 1.506(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C1 1.506(18) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I002 Sn00 I002 180.00(4) 5_656 . ?
I003 Sn00 I002 89.94(3) . 5_656 ?
I003 Sn00 I002 90.06(3) . . ?
I003 Sn00 I002 89.94(3) 5_656 . ?
I003 Sn00 I002 90.06(3) 5_656 5_656 ?
I003 Sn00 I003 180.0 5_656 . ?
Sn00 I002 Sn00 113.03(2) . 4_566 ?
H00A N004 H00B 109.5 . . ?
H00A N004 H00C 109.5 . . ?
H00B N004 H00C 109.5 . . ?
C005 N004 H00A 109.5 . . ?
C005 N004 H00B 109.5 . . ?
C005 N004 H00C 109.5 . . ?
N004 C005 H005 107.1 . . ?
N004 C005 C007 111.0(16) . . ?
C006 C005 N004 108.5(17) . . ?
C006 C005 H005 107.1 . . ?
C006 C005 C007 115.8(19) . . ?
C007 C005 H005 107.1 . . ?
C005 C006 H00D 109.5 . . ?
C005 C006 H00E 109.5 . . ?
C005 C006 H00F 109.5 . . ?
H00D C006 H00E 109.5 . . ?
H00D C006 H00F 109.5 . . ?
H00E C006 H00F 109.5 . . ?
C005 C007 H00G 108.1 . . ?
C005 C007 H00H 108.1 . . ?
H00G C007 H00H 107.3 . . ?
C6 C007 C005 117(2) . . ?
C6 C007 H00G 108.1 . . ?
C6 C007 H00H 108.1 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 C6 111(2) . . ?
C007 C6 C5 112(2) . . ?
C007 C6 H6A 109.2 . . ?
C007 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
C5 C1 H1A 108.8 . . ?
C5 C1 H1B 108.8 . . ?
C9 C1 C5 114(2) . . ?
C9 C1 H1A 108.8 . . ?
C9 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?

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
N004 C005 C007 C6 166(2) . . . . ?
C005 C007 C6 C5 -179(2) . . . . ?
C006 C005 C007 C6 -70(3) . . . . ?
C6 C5 C1 C9 175(3) . . . . ?
C1 C5 C6 C007 -174(3) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Samples, still in the mother liquor, were opened in air and crystals were coated in paratone oil and transfered to a glass slide. Crystals were mounted on a Mitigen loop using paratone oil and quickly placed under a stream of nitrogen for screening and collection.'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.851
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
####################################################################### 
# 
# 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_ec1-187_akash_1mehasni_80k
_database_code_depnum_ccdc_archive 'CCDC 2255224'
loop_
_audit_author_name
_audit_author_address
'Ethan Crace'
;Duke University
United States of America
;
_audit_update_record             
;
2023-04-10 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;
_audit_creation_date             2023-01-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'catena-[bis(heptan-2-ammonium) bis(mu-iodo)-diiodo-tin]'
_chemical_formula_moiety         'I4 Sn, 2(C7 H18 N)'
_chemical_formula_sum            'C14 H36 I4 N2 Sn'
_chemical_formula_weight         858.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N Sn I'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.04641(16)
_cell_length_b                   8.47695(15)
_cell_length_c                   34.0759(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2613.15(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    31503
_cell_measurement_temperature    80.0(8)
_cell_measurement_theta_max      30.9320
_cell_measurement_theta_min      2.3930
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.513
_exptl_absorpt_coefficient_mu    5.702
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.441
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-10 6 -19 0.0299
11 -4 18 0.0329
10 7 3 0.0517
-11 -6 -5 0.0300
-2 -2 -47 0.0064
2 2 47 0.0024

_exptl_crystal_preparation       
'Crystals were grown by slow cooling tin (II) iodide and racemic 2-aminoheptane in hydroiodic acid with hypophosphorous acid as a stabilizer. Samples were left sealed until use.'
_exptl_crystal_recrystallization_method 'See preparation details.'
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.009
_exptl_crystal_size_rad          0.400
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9.8870 5.8070 -19.4153 0.0319 0.1290 0.9911
10.9196 -4.1575 18.3699 -0.0687 -0.2825 -0.9568
10.3548 6.9416 2.5931 -0.2268 -0.9433 -0.2423
-11.0971 -5.7468 -5.0845 0.2179 0.9059 0.3631
-2.4833 -1.6465 -46.6497 0.8900 -0.0230 0.4553
2.4833 1.6465 46.6497 -0.8900 0.0230 -0.4553

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            103955
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.872
_diffrn_reflns_theta_min         2.391
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      80.0(8)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  78.40   0.80   50.00    --    4.40  19.00  60.00  108
  2  ω    -18.00  70.00   0.80   50.00    --   -5.65  25.00 -70.33  110
  3  ω    -24.00  42.40   0.80   50.00    --    4.40  90.00-139.00   83
  4  ω    -18.00  67.60   0.80   50.00    --   -5.65  37.00 120.00  107
  5  ω    -18.00  67.60   0.80   50.00    --   -5.65  37.00  30.00  107
  6  ω    -18.00  70.00   0.80   50.00    --   -5.65  19.00-120.00  110
  7  ω    -18.00  67.60   0.80   50.00    --   -5.65  31.00-172.29  107
  8  ω    -18.00  67.60   0.80   50.00    --   -5.65  37.00 -30.00  107
  9  ω    -18.00  68.40   0.80   50.00    --   -5.65  32.00  81.23  108
 10  ω    -18.00  67.60   0.80   50.00    --   -5.65  31.00-100.42  107
 11  ω    -23.00  27.40   0.80   50.00    --   -5.65 -99.00-120.00   63
 12  ω    -42.00  32.40   0.80   50.00    --    4.40 -90.00 106.00   93
 13  ω    -41.00  21.40   0.80   50.00    --   -5.65 -90.00 106.00   78
 14  ω    -34.00  42.00   0.80   50.00    --   -5.65  90.00-139.00   95
 15  ω    -46.00  -2.00   0.80   50.00    --   -5.65 111.00 -49.37   55
 16  ω    -47.00  -5.40   0.80   50.00    --   -5.65 113.00  44.20   52
 17  ω    -47.00  -5.40   0.80   50.00    --   -5.65 113.00-129.55   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0091980000
_diffrn_orient_matrix_UB_12      -0.0396032000
_diffrn_orient_matrix_UB_13      -0.0181712000
_diffrn_orient_matrix_UB_21      -0.0557731000
_diffrn_orient_matrix_UB_22      -0.0547124000
_diffrn_orient_matrix_UB_23      0.0053920000
_diffrn_orient_matrix_UB_31      -0.0543410000
_diffrn_orient_matrix_UB_32      0.0493718000
_diffrn_orient_matrix_UB_33      -0.0086097000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_special_details          
'As the collection continued, icing was observed on the crystal. This leads to rings appearing in later frames.'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2818
_reflns_number_total             3117
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         1.434
_refine_diff_density_min         -1.421
_refine_diff_density_rms         0.186
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.478
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         3117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.478
_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)+34.3898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C6(H6)
1.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C2(H2A,H2B)
1.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.80545(5) 0.68957(5) 0.49798(2) 0.01820(11) Uani 1 1 d . . . . .
Sn2 Sn 0.500000 0.500000 0.500000 0.01906(15) Uani 1 2 d S . P . .
I2 I 0.47933(6) 0.49577(7) 0.40776(2) 0.02580(13) Uani 1 1 d . . . . .
N1 N 0.1002(8) 0.5860(8) 0.42395(19) 0.0265(15) Uani 1 1 d . . . . .
H1A H 0.060999 0.683332 0.419691 0.032 Uiso 1 1 calc R U . . .
H1B H 0.200576 0.593027 0.424595 0.032 Uiso 1 1 calc R U . . .
H1C H 0.066845 0.547666 0.447266 0.032 Uiso 1 1 calc R U . . .
C6 C 0.0541(10) 0.4760(10) 0.3911(2) 0.0270(17) Uani 1 1 d . . . . .
H6 H 0.109802 0.374519 0.393486 0.032 Uiso 1 1 calc R U . . .
C8 C 0.0889(12) 0.4502(12) 0.3177(3) 0.040(2) Uani 1 1 d . . . . .
H8A H -0.013021 0.408637 0.315381 0.048 Uiso 1 1 calc R U . . .
H8B H 0.155958 0.359516 0.321973 0.048 Uiso 1 1 calc R U . . .
C9 C 0.1309(13) 0.5320(14) 0.2795(3) 0.045(3) Uani 1 1 d . . . . .
H9A H 0.068867 0.627556 0.276695 0.054 Uiso 1 1 calc R U . . .
H9B H 0.234945 0.567305 0.281586 0.054 Uiso 1 1 calc R U . . .
C10 C 0.0973(10) 0.5588(11) 0.3525(2) 0.0298(18) Uani 1 1 d . . . . .
H10A H 0.030580 0.649653 0.348186 0.036 Uiso 1 1 calc R U . . .
H10B H 0.199338 0.599915 0.354902 0.036 Uiso 1 1 calc R U . . .
C5 C -0.1077(10) 0.4441(13) 0.3948(3) 0.038(2) Uani 1 1 d . . . . .
H5A H -0.127042 0.388760 0.419529 0.057 Uiso 1 1 calc R U . . .
H5B H -0.140295 0.378500 0.372767 0.057 Uiso 1 1 calc R U . . .
H5C H -0.161945 0.544184 0.394532 0.057 Uiso 1 1 calc R U . . .
C3 C 0.1502(17) 0.516(2) 0.2055(3) 0.080(5) Uani 1 1 d . . . . .
H3A H 0.128580 0.444993 0.183505 0.121 Uiso 1 1 calc R U . . .
H3B H 0.255132 0.544438 0.205065 0.121 Uiso 1 1 calc R U . . .
H3C H 0.089888 0.611401 0.203161 0.121 Uiso 1 1 calc R U . . .
C2 C 0.1155(17) 0.4354(16) 0.2428(3) 0.065(4) Uani 1 1 d . . . . .
H2A H 0.180786 0.342188 0.245184 0.078 Uiso 1 1 calc R U . . .
H2B H 0.012514 0.396267 0.241364 0.078 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 Sn2 3.1666(4) 3_566 ?
I1 Sn2 3.1972(4) . ?
Sn2 I2 3.1490(5) 5_666 ?
Sn2 I2 3.1490(5) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C6 1.514(10) . ?
C6 H6 1.0000 . ?
C6 C10 1.542(11) . ?
C6 C5 1.494(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.523(13) . ?
C8 C10 1.505(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C2 1.501(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 C2 1.476(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

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
Sn2 I1 Sn2 153.840(16) 3_566 . ?
I1 Sn2 I1 93.620(4) 7_755 5_666 ?
I1 Sn2 I1 93.620(4) 3_466 . ?
I1 Sn2 I1 180.000(16) 7_755 3_466 ?
I1 Sn2 I1 86.380(4) 3_466 5_666 ?
I1 Sn2 I1 86.380(4) 7_755 . ?
I1 Sn2 I1 180.0 . 5_666 ?
I2 Sn2 I1 87.962(13) 5_666 . ?
I2 Sn2 I1 90.106(13) . 7_755 ?
I2 Sn2 I1 87.962(13) . 5_666 ?
I2 Sn2 I1 89.894(13) . 3_466 ?
I2 Sn2 I1 92.039(13) . . ?
I2 Sn2 I1 92.037(13) 5_666 5_666 ?
I2 Sn2 I1 89.894(13) 5_666 7_755 ?
I2 Sn2 I1 90.106(13) 5_666 3_466 ?
I2 Sn2 I2 180.00(2) 5_666 . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C6 N1 H1A 109.5 . . ?
C6 N1 H1B 109.5 . . ?
C6 N1 H1C 109.5 . . ?
N1 C6 H6 109.4 . . ?
N1 C6 C10 106.2(6) . . ?
C10 C6 H6 109.4 . . ?
C5 C6 N1 108.6(7) . . ?
C5 C6 H6 109.4 . . ?
C5 C6 C10 113.7(7) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C10 C8 H8A 109.1 . . ?
C10 C8 H8B 109.1 . . ?
C10 C8 C9 112.5(8) . . ?
C8 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C2 C9 C8 116.1(10) . . ?
C2 C9 H9A 108.3 . . ?
C2 C9 H9B 108.3 . . ?
C6 C10 H10A 109.1 . . ?
C6 C10 H10B 109.1 . . ?
C8 C10 C6 112.5(7) . . ?
C8 C10 H10A 109.1 . . ?
C8 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
C9 C2 H2A 108.2 . . ?
C9 C2 H2B 108.2 . . ?
C3 C2 C9 116.5(12) . . ?
C3 C2 H2A 108.2 . . ?
C3 C2 H2B 108.2 . . ?
H2A C2 H2B 107.3 . . ?

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 C6 C10 C8 167.6(7) . . . . ?
C8 C9 C2 C3 177.6(11) . . . . ?
C9 C8 C10 C6 179.7(8) . . . . ?
C10 C8 C9 C2 -175.9(10) . . . . ?
C5 C6 C10 C8 -72.9(10) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Samples, still in the mother liquor, were opened in air and crystals were coated in paratone oil and transfered to a glass slide. Crystals were mounted on a Mitegen loop using paratone oil and quickly placed under a stream of nitrogen for screening and collection. '
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.277
_oxdiff_exptl_absorpt_empirical_full_min 0.710
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
