 
data_p21
 
_audit_creation_method            SHELXL-2014
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C16 H32 Cl6 N2 Sn'
_chemical_formula_sum
 'C16 H32 Cl6 N2 Sn' 
_chemical_formula_weight          583.82

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Sn'  'Sn'  -0.6537   1.4246
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    8.4404(4)
_cell_length_b                    9.3829(5)
_cell_length_c                    17.6920(10)
_cell_angle_alpha                 90
_cell_angle_beta                  115.385(4)
_cell_angle_gamma                 90
_cell_volume                      1265.84(12)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     4282 
_cell_measurement_theta_min       4.3960 
_cell_measurement_theta_max       28.6250 
 
_exptl_crystal_description         block 
_exptl_crystal_colour             white 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.532          
_exptl_crystal_F_000              588
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.210
_exptl_crystal_size_mid           0.190
_exptl_crystal_size_min           0.190
_exptl_absorpt_coefficient_mu     1.647
_shelx_estimated_absorpt_T_min    0.724
_shelx_estimated_absorpt_T_max    0.745
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.715
_exptl_absorpt_correction_T_max   0.731
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'micro-focus sealed X-ray tube'                      
_diffrn_measurement_device_type   'SuperNova, Single source at offset, EosS2' 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             7586
_diffrn_reflns_av_unetI/netI      0.0350
_diffrn_reflns_av_R_equivalents   0.0310
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.348
_diffrn_reflns_theta_max          25.026
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.958
_diffrn_measured_fraction_theta_full  0.972
_diffrn_reflns_Laue_measured_fraction_max    0.958
_diffrn_reflns_Laue_measured_fraction_full   0.972
_diffrn_reflns_point_group_measured_fraction_max   0.958
_diffrn_reflns_point_group_measured_fraction_full  0.972
_reflns_number_total              2252
_reflns_number_gt                 2087
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction         'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution     'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics     'SHELXL-2014 (Sheldrick, 2014)'
 
_refine_special_details
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0653P)²+17.7209P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2252
_refine_ls_number_parameters      126
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0704
_refine_ls_R_factor_gt            0.0650
_refine_ls_wR_factor_ref          0.1950
_refine_ls_wR_factor_gt           0.1864
_refine_ls_goodness_of_fit_ref    1.219
_refine_ls_restrained_S_all       1.219
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Sn1 Sn 0.5000 0.0000 0.0000 0.0260(3) Uani 1 2 d S . P . .
Cl1 Cl 0.7306(4) 0.1733(3) 0.02693(17) 0.0410(7) Uani 1 1 d . . . . .
Cl2 Cl 0.6455(4) -0.0766(3) 0.14569(15) 0.0415(7) Uani 1 1 d . . . . .
Cl3 Cl 0.3360(4) 0.1742(3) 0.03958(19) 0.0441(7) Uani 1 1 d . . . . .
N1 N 0.8019(11) 0.3227(10) 0.2962(5) 0.036(2) Uani 1 1 d . . . . .
C1 C 0.6318(17) 0.3887(16) 0.2350(9) 0.055(3) Uani 1 1 d . . . . .
H1A H 0.5611 0.4124 0.2643 0.066 Uiso 1 1 calc R U . . .
H1B H 0.5676 0.3191 0.1923 0.066 Uiso 1 1 calc R U . . .
C2 C 0.658(2) 0.5224(15) 0.1930(9) 0.062(4) Uani 1 1 d . . . . .
C3 C 0.619(2) 0.5281(16) 0.1149(10) 0.077(5) Uani 1 1 d . . . . .
H3A H 0.5733 0.4485 0.0813 0.093 Uiso 1 1 calc R U . . .
H3B H 0.6374 0.6119 0.0916 0.093 Uiso 1 1 calc R U . . .
C4 C 0.7477(19) 0.1957(15) 0.3327(8) 0.055(3) Uani 1 1 d . . . . .
H4A H 0.6846 0.2298 0.3638 0.066 Uiso 1 1 calc R U . . .
H4B H 0.6680 0.1368 0.2873 0.066 Uiso 1 1 calc R U . . .
C5 C 0.898(2) 0.1059(18) 0.3893(8) 0.064(4) Uani 1 1 d . . . . .
C6 C 0.905(2) -0.0278(18) 0.3798(10) 0.076(5) Uani 1 1 d . . . . .
H6A H 0.8139 -0.0739 0.3363 0.092 Uiso 1 1 calc R U . . .
H6B H 1.0013 -0.0796 0.4165 0.092 Uiso 1 1 calc R U . . .
C7 C 0.8962(19) 0.4274(14) 0.3636(8) 0.054(3) Uani 1 1 d . . . . .
H7A H 0.9997 0.3838 0.4053 0.082 Uiso 1 1 calc R U . . .
H7B H 0.8210 0.4573 0.3888 0.082 Uiso 1 1 calc R U . . .
H7C H 0.9287 0.5086 0.3404 0.082 Uiso 1 1 calc R U . . .
C8 C 0.9056(18) 0.2746(17) 0.2523(9) 0.056(4) Uani 1 1 d . . . . .
H8A H 0.9259 0.3535 0.2231 0.084 Uiso 1 1 calc R U . . .
H8B H 0.8427 0.2013 0.2131 0.084 Uiso 1 1 calc R U . . .
H8C H 1.0159 0.2376 0.2922 0.084 Uiso 1 1 calc R U . . .
H5 H 1.00(2) 0.148(17) 0.438(10) 0.07(5) Uiso 1 1 d . . . . .
H2 H 0.684(16) 0.614(14) 0.227(8) 0.05(3) Uiso 1 1 d . . . . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
Sn1 0.0286(5) 0.0269(5) 0.0205(5) 0.0001(4) 0.0085(4) -0.0022(5)
Cl1 0.0418(15) 0.0409(15) 0.0398(15) -0.0040(12) 0.0171(12) -0.0155(13)
Cl2 0.0452(15) 0.0495(16) 0.0232(12) 0.0079(11) 0.0083(11) -0.0006(14)
Cl3 0.0442(15) 0.0419(16) 0.0480(17) -0.0092(13) 0.0216(13) 0.0046(13)
N1 0.032(5) 0.043(5) 0.032(5) -0.004(4) 0.013(4) -0.003(4)
C1 0.038(7) 0.064(9) 0.056(8) 0.000(7) 0.014(6) 0.003(6)
C2 0.068(9) 0.040(7) 0.061(9) 0.001(7) 0.013(7) -0.002(7)
C3 0.113(14) 0.047(8) 0.057(9) 0.011(7) 0.022(9) 0.004(9)
C4 0.062(8) 0.057(8) 0.048(7) -0.005(6) 0.027(7) -0.015(7)
C5 0.072(10) 0.072(10) 0.032(7) 0.011(7) 0.008(7) 0.004(9)
C6 0.095(12) 0.077(12) 0.049(8) 0.017(8) 0.023(8) 0.018(10)
C7 0.066(9) 0.048(7) 0.044(7) -0.012(6) 0.020(7) -0.004(7)
C8 0.050(7) 0.073(10) 0.052(8) -0.004(7) 0.029(6) 0.003(7)
 
_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 Cl1 2.421(3) 3_655 ?
Sn1 Cl1 2.421(3) . ?
Sn1 Cl3 2.431(3) 3_655 ?
Sn1 Cl3 2.431(3) . ?
Sn1 Cl2 2.440(2) 3_655 ?
Sn1 Cl2 2.440(2) . ?
N1 C8 1.467(15) . ?
N1 C7 1.486(15) . ?
N1 C1 1.511(15) . ?
N1 C4 1.517(16) . ?
C1 C2 1.52(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.28(2) . ?
C2 H2 1.01(13) . ?
C3 H3A 0.9300 . ?
C3 H3B 0.9300 . ?
C4 C5 1.49(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.27(2) . ?
C5 H5 1.02(16) . ?
C6 H6A 0.9300 . ?
C6 H6B 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
Cl1 Sn1 Cl1 180.0 3_655 . ?
Cl1 Sn1 Cl3 90.05(10) 3_655 3_655 ?
Cl1 Sn1 Cl3 89.95(10) . 3_655 ?
Cl1 Sn1 Cl3 89.95(10) 3_655 . ?
Cl1 Sn1 Cl3 90.05(10) . . ?
Cl3 Sn1 Cl3 180.0 3_655 . ?
Cl1 Sn1 Cl2 89.53(10) 3_655 3_655 ?
Cl1 Sn1 Cl2 90.47(10) . 3_655 ?
Cl3 Sn1 Cl2 89.12(10) 3_655 3_655 ?
Cl3 Sn1 Cl2 90.88(10) . 3_655 ?
Cl1 Sn1 Cl2 90.47(10) 3_655 . ?
Cl1 Sn1 Cl2 89.53(10) . . ?
Cl3 Sn1 Cl2 90.88(10) 3_655 . ?
Cl3 Sn1 Cl2 89.12(10) . . ?
Cl2 Sn1 Cl2 180.0 3_655 . ?
C8 N1 C7 113.1(10) . . ?
C8 N1 C1 110.3(10) . . ?
C7 N1 C1 108.8(10) . . ?
C8 N1 C4 109.9(10) . . ?
C7 N1 C4 109.4(9) . . ?
C1 N1 C4 105.0(10) . . ?
N1 C1 C2 113.3(11) . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 122.7(14) . . ?
C3 C2 H2 119(7) . . ?
C1 C2 H2 117(7) . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?
C5 C4 N1 113.8(12) . . ?
C5 C4 H4A 108.8 . . ?
N1 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
N1 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 122.9(16) . . ?
C6 C5 H5 115(9) . . ?
C4 C5 H5 122(9) . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
 
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
C8 N1 C1 C2 -63.4(15) . . . . ?
C7 N1 C1 C2 61.2(14) . . . . ?
C4 N1 C1 C2 178.2(11) . . . . ?
N1 C1 C2 C3 113.0(18) . . . . ?
C8 N1 C4 C5 55.7(14) . . . . ?
C7 N1 C4 C5 -69.1(14) . . . . ?
C1 N1 C4 C5 174.3(12) . . . . ?
N1 C4 C5 C6 -126.9(17) . . . . ?
 
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 
C7 H7A Cl3  0.96 2.87 3.804(14) 165.7 4_666
C4 H4A Cl1  0.97 2.89 3.710(14) 143.1 4_566
C1 H1B Cl3  0.97 2.90 3.852(15) 165.6 .
C1 H1A Cl2  0.97 2.82 3.779(15) 168.8 2_655
C7 H7A Cl3  0.96 2.87 3.804(14) 165.7 4_666
C4 H4A Cl1  0.97 2.89 3.710(14) 143.1 4_566
C1 H1A Cl2  0.97 2.82 3.779(15) 168.8 2_655
 
_refine_diff_density_max    2.445
_refine_diff_density_min   -1.047
_refine_diff_density_rms    0.198

_shelxl_version_number 2014-3