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#$Date: 2022-11-08 12:30:56 +0200 (Tue, 08 Nov 2022) $
#$Revision: 279099 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106020.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106020
loop_
_publ_author_name
'Lee, See Mun'
'Lo, Kong Mun'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of
 (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV),
 C24H20Cl4N2Sn
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1321
_journal_page_last               1323
_journal_paper_doi               10.1515/ncrs-2019-0508
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C24 H20 Cl4 N2 Sn'
_chemical_formula_sum            'C24 H20 Cl4 N2 Sn'
_chemical_formula_weight         596.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.0770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.79440(10)
_cell_length_b                   21.1245(2)
_cell_length_c                   14.76110(10)
_cell_measurement_reflns_used    16828
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1170
_cell_measurement_theta_min      3.6390
_cell_volume                     2420.92(4)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2014/7 [3]'
_computing_structure_refinement  'SHELXL-2014/7 [3]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30103
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.663
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    12.570
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0229
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0360P)²+1.0214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0603
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3987
_reflns_number_total             4329
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0508_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106020
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.276
_shelx_estimated_absorpt_t_max   0.640
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Sn Sn 0.56304(2) 0.69771(2) 0.57470(2) 0.02011(6) Uani 1 1 d . . . . .
Cl1 Cl 0.65370(8) 0.76490(3) 0.71076(4) 0.03300(14) Uani 1 1 d . . . . .
Cl2 Cl 0.46362(8) 0.59790(3) 0.64596(4) 0.03040(14) Uani 1 1 d . . . . .
Cl3 Cl 0.98078(10) 0.50596(4) 0.25670(5) 0.0559(2) Uani 1 1 d . . . . .
Cl4 Cl 0.16551(14) 0.98789(4) 0.39746(5) 0.0602(2) Uani 1 1 d . . . . .
N1 N 0.6389(2) 0.77422(9) 0.47038(12) 0.0220(4) Uani 1 1 d . . . . .
N2 N 0.4981(3) 0.66045(9) 0.42577(13) 0.0237(4) Uani 1 1 d . . . . .
C1 C 0.8256(3) 0.66250(12) 0.57962(17) 0.0293(5) Uani 1 1 d . . . . .
H1A H 0.9052 0.6991 0.5846 0.035 Uiso 1 1 calc R U . . .
H1B H 0.8487 0.6368 0.6354 0.035 Uiso 1 1 calc R U . . .
C2 C 0.8653(3) 0.62366(12) 0.50031(18) 0.0274(5) Uani 1 1 d . . . . .
C3 C 0.9441(3) 0.65035(13) 0.42807(17) 0.0295(6) Uani 1 1 d . . . . .
H3 H 0.9741 0.6939 0.4302 0.035 Uiso 1 1 calc R U . . .
C4 C 0.9793(3) 0.61458(14) 0.35337(18) 0.0347(6) Uani 1 1 d . . . . .
H4 H 1.0346 0.6332 0.3051 0.042 Uiso 1 1 calc R U . . .
C5 C 0.9331(3) 0.55163(14) 0.35000(19) 0.0361(6) Uani 1 1 d . . . . .
C6 C 0.8530(3) 0.52352(14) 0.4196(2) 0.0403(7) Uani 1 1 d . . . . .
H6 H 0.8211 0.4801 0.4163 0.048 Uiso 1 1 calc R U . . .
C7 C 0.8204(3) 0.55973(13) 0.4940(2) 0.0357(6) Uani 1 1 d . . . . .
H7 H 0.7659 0.5406 0.5421 0.043 Uiso 1 1 calc R U . . .
C8 C 0.3035(3) 0.73429(11) 0.57325(16) 0.0245(5) Uani 1 1 d . . . . .
H8A H 0.2244 0.7033 0.5412 0.029 Uiso 1 1 calc R U . . .
H8B H 0.2731 0.7367 0.6369 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2704(3) 0.79740(11) 0.53029(16) 0.0234(5) Uani 1 1 d . . . . .
C10 C 0.2932(3) 0.85329(12) 0.58044(16) 0.0270(5) Uani 1 1 d . . . . .
H10 H 0.3307 0.8510 0.6434 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2624(4) 0.91181(13) 0.54036(17) 0.0332(6) Uani 1 1 d . . . . .
H11 H 0.2767 0.9495 0.5753 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2103(4) 0.91449(12) 0.44805(18) 0.0338(6) Uani 1 1 d . . . . .
C13 C 0.1897(3) 0.86048(13) 0.39608(16) 0.0293(5) Uani 1 1 d . . . . .
H13 H 0.1553 0.8632 0.3328 0.035 Uiso 1 1 calc R U . . .
C14 C 0.2197(3) 0.80247(11) 0.43712(17) 0.0245(5) Uani 1 1 d . . . . .
H14 H 0.2058 0.7651 0.4015 0.029 Uiso 1 1 calc R U . . .
C15 C 0.7005(3) 0.83109(12) 0.49631(17) 0.0290(5) Uani 1 1 d . . . . .
H15 H 0.7154 0.8406 0.5594 0.035 Uiso 1 1 calc R U . . .
C16 C 0.7434(4) 0.87653(13) 0.4348(2) 0.0368(6) Uani 1 1 d . . . . .
H16 H 0.7898 0.9162 0.4551 0.044 Uiso 1 1 calc R U . . .
C17 C 0.7174(4) 0.86304(13) 0.3438(2) 0.0408(7) Uani 1 1 d . . . . .
H17 H 0.7455 0.8935 0.3000 0.049 Uiso 1 1 calc R U . . .
C18 C 0.6503(4) 0.80501(12) 0.31598(19) 0.0339(6) Uani 1 1 d . . . . .
H18 H 0.6292 0.7957 0.2530 0.041 Uiso 1 1 calc R U . . .
C19 C 0.6136(3) 0.76016(11) 0.38062(15) 0.0227(5) Uani 1 1 d . . . . .
C20 C 0.5476(3) 0.69619(11) 0.35705(16) 0.0219(5) Uani 1 1 d . . . . .
C21 C 0.5388(3) 0.67292(13) 0.26900(16) 0.0301(5) Uani 1 1 d . . . . .
H21 H 0.5729 0.6985 0.2208 0.036 Uiso 1 1 calc R U . . .
C22 C 0.4795(3) 0.61185(14) 0.25209(17) 0.0336(6) Uani 1 1 d . . . . .
H22 H 0.4758 0.5949 0.1923 0.040 Uiso 1 1 calc R U . . .
C23 C 0.4262(3) 0.57587(13) 0.32175(18) 0.0340(6) Uani 1 1 d . . . . .
H23 H 0.3828 0.5343 0.3110 0.041 Uiso 1 1 calc R U . . .
C24 C 0.4377(3) 0.60198(12) 0.40811(18) 0.0307(6) Uani 1 1 d . . . . .
H24 H 0.4012 0.5774 0.4568 0.037 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn 0.0259 5.4591 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C8 Sn C1 178.39(9) . .
C8 Sn N1 92.14(8) . .
C1 Sn N1 88.07(8) . .
C8 Sn N2 89.22(8) . .
C1 Sn N2 92.35(8) . .
N1 Sn N2 70.25(7) . .
C8 Sn Cl1 90.16(7) . .
C1 Sn Cl1 88.23(7) . .
N1 Sn Cl1 93.80(5) . .
N2 Sn Cl1 164.00(5) . .
C8 Sn Cl2 88.91(6) . .
C1 Sn Cl2 91.33(7) . .
N1 Sn Cl2 163.73(5) . .
N2 Sn Cl2 93.54(5) . .
Cl1 Sn Cl2 102.43(2) . .
C15 N1 C19 119.6(2) . .
C15 N1 Sn 122.45(15) . .
C19 N1 Sn 117.89(15) . .
C24 N2 C20 119.3(2) . .
C24 N2 Sn 122.31(16) . .
C20 N2 Sn 117.67(15) . .
C2 C1 Sn 115.12(16) . .
C2 C1 H1A 108.5 . .
Sn C1 H1A 108.5 . .
C2 C1 H1B 108.5 . .
Sn C1 H1B 108.5 . .
H1A C1 H1B 107.5 . .
C3 C2 C7 117.7(2) . .
C3 C2 C1 121.1(2) . .
C7 C2 C1 121.3(2) . .
C4 C3 C2 121.3(3) . .
C4 C3 H3 119.3 . .
C2 C3 H3 119.3 . .
C3 C4 C5 119.1(3) . .
C3 C4 H4 120.5 . .
C5 C4 H4 120.5 . .
C6 C5 C4 121.4(3) . .
C6 C5 Cl3 119.3(2) . .
C4 C5 Cl3 119.2(2) . .
C7 C6 C5 118.7(3) . .
C7 C6 H6 120.6 . .
C5 C6 H6 120.6 . .
C6 C7 C2 121.8(3) . .
C6 C7 H7 119.1 . .
C2 C7 H7 119.1 . .
C9 C8 Sn 116.77(16) . .
C9 C8 H8A 108.1 . .
Sn C8 H8A 108.1 . .
C9 C8 H8B 108.1 . .
Sn C8 H8B 108.1 . .
H8A C8 H8B 107.3 . .
C10 C9 C14 117.9(2) . .
C10 C9 C8 121.5(2) . .
C14 C9 C8 120.6(2) . .
C11 C10 C9 121.3(2) . .
C11 C10 H10 119.3 . .
C9 C10 H10 119.3 . .
C10 C11 C12 118.8(2) . .
C10 C11 H11 120.6 . .
C12 C11 H11 120.6 . .
C13 C12 C11 121.5(2) . .
C13 C12 Cl4 119.3(2) . .
C11 C12 Cl4 119.1(2) . .
C12 C13 C14 119.0(2) . .
C12 C13 H13 120.5 . .
C14 C13 H13 120.5 . .
C13 C14 C9 121.5(2) . .
C13 C14 H14 119.3 . .
C9 C14 H14 119.3 . .
N1 C15 C16 122.5(2) . .
N1 C15 H15 118.8 . .
C16 C15 H15 118.8 . .
C17 C16 C15 118.4(3) . .
C17 C16 H16 120.8 . .
C15 C16 H16 120.8 . .
C16 C17 C18 119.6(3) . .
C16 C17 H17 120.2 . .
C18 C17 H17 120.2 . .
C17 C18 C19 119.7(3) . .
C17 C18 H18 120.1 . .
C19 C18 H18 120.1 . .
N1 C19 C18 120.0(2) . .
N1 C19 C20 116.7(2) . .
C18 C19 C20 123.3(2) . .
N2 C20 C21 120.9(2) . .
N2 C20 C19 116.9(2) . .
C21 C20 C19 122.2(2) . .
C20 C21 C22 119.2(2) . .
C20 C21 H21 120.4 . .
C22 C21 H21 120.4 . .
C23 C22 C21 119.9(2) . .
C23 C22 H22 120.0 . .
C21 C22 H22 120.0 . .
C22 C23 C24 118.0(2) . .
C22 C23 H23 121.0 . .
C24 C23 H23 121.0 . .
N2 C24 C23 122.7(2) . .
N2 C24 H24 118.7 . .
C23 C24 H24 118.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn C8 2.164(2) .
Sn C1 2.173(2) .
Sn N1 2.3439(19) .
Sn N2 2.3478(19) .
Sn Cl1 2.5093(6) .
Sn Cl2 2.5094(6) .
Cl3 C5 1.748(3) .
Cl4 C12 1.743(3) .
N1 C15 1.337(3) .
N1 C19 1.355(3) .
N2 C24 1.339(3) .
N2 C20 1.348(3) .
C1 C2 1.484(4) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.396(4) .
C2 C7 1.396(4) .
C3 C4 1.384(4) .
C3 H3 0.9500 .
C4 C5 1.378(4) .
C4 H4 0.9500 .
C5 C6 1.382(4) .
C6 C7 1.380(4) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 C9 1.489(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.397(3) .
C9 C14 1.401(3) .
C10 C11 1.382(4) .
C10 H10 0.9500 .
C11 C12 1.388(4) .
C11 H11 0.9500 .
C12 C13 1.376(4) .
C13 C14 1.378(3) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C16 1.382(4) .
C15 H15 0.9500 .
C16 C17 1.371(4) .
C16 H16 0.9500 .
C17 C18 1.381(4) .
C17 H17 0.9500 .
C18 C19 1.392(3) .
C18 H18 0.9500 .
C19 C20 1.476(3) .
C20 C21 1.385(3) .
C21 C22 1.386(4) .
C21 H21 0.9500 .
C22 C23 1.372(4) .
C22 H22 0.9500 .
C23 C24 1.385(4) .
C23 H23 0.9500 .
C24 H24 0.9500 .
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
Sn C1 C2 C3 96.9(2) . . . .
Sn C1 C2 C7 -81.0(3) . . . .
C7 C2 C3 C4 -1.1(3) . . . .
C1 C2 C3 C4 -179.1(2) . . . .
C2 C3 C4 C5 1.0(4) . . . .
C3 C4 C5 C6 -0.2(4) . . . .
C3 C4 C5 Cl3 -178.89(19) . . . .
C4 C5 C6 C7 -0.4(4) . . . .
Cl3 C5 C6 C7 178.3(2) . . . .
C5 C6 C7 C2 0.3(4) . . . .
C3 C2 C7 C6 0.5(4) . . . .
C1 C2 C7 C6 178.5(2) . . . .
Sn C8 C9 C10 -89.0(2) . . . .
Sn C8 C9 C14 89.2(2) . . . .
C14 C9 C10 C11 1.8(4) . . . .
C8 C9 C10 C11 180.0(2) . . . .
C9 C10 C11 C12 -1.0(4) . . . .
C10 C11 C12 C13 -0.3(4) . . . .
C10 C11 C12 Cl4 178.3(2) . . . .
C11 C12 C13 C14 0.8(4) . . . .
Cl4 C12 C13 C14 -177.8(2) . . . .
C12 C13 C14 C9 0.1(4) . . . .
C10 C9 C14 C13 -1.3(4) . . . .
C8 C9 C14 C13 -179.5(2) . . . .
C19 N1 C15 C16 -1.3(4) . . . .
Sn N1 C15 C16 -179.2(2) . . . .
N1 C15 C16 C17 1.7(4) . . . .
C15 C16 C17 C18 -0.2(4) . . . .
C16 C17 C18 C19 -1.6(4) . . . .
C15 N1 C19 C18 -0.5(3) . . . .
Sn N1 C19 C18 177.47(18) . . . .
C15 N1 C19 C20 179.2(2) . . . .
Sn N1 C19 C20 -2.8(3) . . . .
C17 C18 C19 N1 2.0(4) . . . .
C17 C18 C19 C20 -177.7(2) . . . .
C24 N2 C20 C21 -0.8(3) . . . .
Sn N2 C20 C21 169.63(17) . . . .
C24 N2 C20 C19 -179.8(2) . . . .
Sn N2 C20 C19 -9.4(3) . . . .
N1 C19 C20 N2 8.1(3) . . . .
C18 C19 C20 N2 -172.2(2) . . . .
N1 C19 C20 C21 -170.9(2) . . . .
C18 C19 C20 C21 8.8(4) . . . .
N2 C20 C21 C22 -0.6(4) . . . .
C19 C20 C21 C22 178.4(2) . . . .
C20 C21 C22 C23 1.7(4) . . . .
C21 C22 C23 C24 -1.5(4) . . . .
C20 N2 C24 C23 1.1(4) . . . .
Sn N2 C24 C23 -168.89(19) . . . .
C22 C23 C24 N2 0.1(4) . . . .
