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#$Date: 2022-11-17 12:32:11 +0200 (Thu, 17 Nov 2022) $
#$Revision: 279365 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106145.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_8106145
loop_
_publ_author_name
'Lee, See Mun'
'Tan, Yee Seng'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of
 {N-(3-ethoxy-2-oxidobenzylidene)-4-fluorobenzohydrazonato-κ3
 O,N,O′}dimethyltin(IV), C18H19FN2O3Sn
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              335
_journal_page_last               337
_journal_paper_doi               10.1515/ncrs-2017-0417
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C18 H19 F N2 O3 Sn'
_chemical_formula_sum            'C18 H19 F N2 O3 Sn'
_chemical_formula_weight         449.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.271(1)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.1120(3)
_cell_length_b                   9.5721(1)
_cell_length_c                   13.3072(1)
_cell_measurement_reflns_used    14460
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0800
_cell_measurement_theta_min      3.3480
_cell_volume                     3417.55(6)
_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  'SHELXL2014/7 [3]'
_computing_structure_refinement  'SHELXL2014/7 [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  0.0207
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19108
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         3.294
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    12.169
_exptl_absorpt_correction_T_max  0.757
_exptl_absorpt_correction_T_min  0.383
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_description       prism
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.139
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0165
_refine_ls_R_factor_gt           0.0159
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0243P)²+3.9591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0421
_refine_ls_wR_factor_ref         0.0425
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2973
_reflns_number_total             3054
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0417_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8106145
_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   0.283
_shelx_estimated_absorpt_t_max   0.470
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 1.03593(2) 0.18572(2) 0.54436(2) 0.01938(5) Uani 1 1 d . . . . .
F1 F 1.23392(4) 0.83093(11) 0.76403(10) 0.0307(3) Uani 1 1 d . . . . .
O1 O 0.95968(4) 0.11587(13) 0.52846(10) 0.0259(3) Uani 1 1 d . . . . .
O2 O 1.09603(5) 0.33896(13) 0.57464(10) 0.0246(3) Uani 1 1 d . . . . .
O3 O 0.87769(16) -0.0365(5) 0.5139(3) 0.0206(8) Uani 0.5 1 d . . P A 1
O3' O 0.87368(17) -0.0243(5) 0.4702(3) 0.0195(8) Uani 0.5 1 d . . P A 2
N1 N 1.00493(5) 0.37540(15) 0.60330(10) 0.0174(3) Uani 1 1 d . . . . .
N2 N 1.03850(5) 0.48275(15) 0.63577(11) 0.0184(3) Uani 1 1 d . . . . .
C1 C 0.91867(7) 0.17438(18) 0.55216(14) 0.0192(4) Uani 1 1 d . . . . .
C2 C 0.91703(7) 0.30860(18) 0.59516(13) 0.0183(4) Uani 1 1 d . . . . .
C3 C 0.87167(7) 0.3645(2) 0.61810(14) 0.0249(4) Uani 1 1 d . . . . .
H3 H 0.8713 0.4552 0.6470 0.030 Uiso 1 1 calc R U . . .
C4 C 0.82829(7) 0.2899(2) 0.59934(15) 0.0270(4) Uani 1 1 d . . . . .
H4 H 0.7980 0.3282 0.6153 0.032 Uiso 1 1 calc R U . . .
C5 C 0.82902(7) 0.1569(2) 0.55643(15) 0.0254(4) Uani 1 1 d . . . . .
H5 H 0.7989 0.1052 0.5427 0.030 Uiso 1 1 calc R U . . .
C6 C 0.87269(7) 0.0997(2) 0.53373(15) 0.0253(4) Uani 1 1 d . . . . .
C7 C 0.95958(6) 0.39878(19) 0.61917(12) 0.0184(3) Uani 1 1 d . . . . .
H7 H 0.9538 0.4854 0.6502 0.022 Uiso 1 1 calc R U . . .
C8 C 1.08356(7) 0.45227(18) 0.61761(12) 0.0181(3) Uani 1 1 d . . . . .
C9 C 1.12316(6) 0.55560(18) 0.65236(12) 0.0174(3) Uani 1 1 d . . . . .
C10 C 1.17296(7) 0.52091(19) 0.65213(14) 0.0223(4) Uani 1 1 d . . . . .
H10 H 1.1813 0.4331 0.6258 0.027 Uiso 1 1 calc R U . . .
C11 C 1.21060(7) 0.6129(2) 0.68982(15) 0.0251(4) Uani 1 1 d . . . . .
H11 H 1.2447 0.5891 0.6904 0.030 Uiso 1 1 calc R U . . .
C12 C 1.19717(7) 0.73946(19) 0.72642(14) 0.0214(4) Uani 1 1 d . . . . .
C13 C 1.14843(7) 0.77872(19) 0.72732(14) 0.0213(4) Uani 1 1 d . . . . .
H13 H 1.1405 0.8671 0.7533 0.026 Uiso 1 1 calc R U . . .
C14 C 1.11134(7) 0.68607(18) 0.68941(14) 0.0204(4) Uani 1 1 d . . . . .
H14 H 1.0774 0.7113 0.6885 0.025 Uiso 1 1 calc R U . . .
C15 C 0.83344(14) -0.1226(4) 0.5047(3) 0.0213(8) Uani 0.5 1 d . . P A 1
H15A H 0.8140 -0.0991 0.5599 0.026 Uiso 0.5 1 calc R U P A 1
H15B H 0.8433 -0.2221 0.5122 0.026 Uiso 0.5 1 calc R U P A 1
C16 C 0.80136(19) -0.1014(5) 0.4034(3) 0.0278(10) Uani 0.5 1 d . . P A 1
H16A H 0.7717 -0.1608 0.3994 0.042 Uiso 0.5 1 calc R U P A 1
H16B H 0.8204 -0.1265 0.3487 0.042 Uiso 0.5 1 calc R U P A 1
H16C H 0.7912 -0.0033 0.3962 0.042 Uiso 0.5 1 calc R U P A 1
C15' C 0.82725(16) -0.0866(4) 0.4251(3) 0.0191(8) Uani 0.5 1 d . . P A 2
H15C H 0.8332 -0.1421 0.3652 0.023 Uiso 0.5 1 calc R U P A 2
H15D H 0.8034 -0.0113 0.4010 0.023 Uiso 0.5 1 calc R U P A 2
C16' C 0.80407(16) -0.1798(4) 0.4971(3) 0.0242(8) Uani 0.5 1 d . . P A 2
H16D H 0.7729 -0.2192 0.4619 0.036 Uiso 0.5 1 calc R U P A 2
H16E H 0.7971 -0.1250 0.5556 0.036 Uiso 0.5 1 calc R U P A 2
H16F H 0.8272 -0.2557 0.5204 0.036 Uiso 0.5 1 calc R U P A 2
C17 C 1.03680(8) 0.2026(2) 0.38741(15) 0.0264(4) Uani 1 1 d . . . . .
H17A H 1.0291 0.1115 0.3553 0.040 Uiso 1 1 calc R U . . .
H17B H 1.0699 0.2330 0.3749 0.040 Uiso 1 1 calc R U . . .
H17C H 1.0118 0.2711 0.3587 0.040 Uiso 1 1 calc R U . . .
C18 C 1.06014(7) 0.0752(2) 0.67942(15) 0.0282(4) Uani 1 1 d . . . . .
H18A H 1.0601 -0.0252 0.6649 0.042 Uiso 1 1 calc R U . . .
H18B H 1.0376 0.0943 0.7291 0.042 Uiso 1 1 calc R U . . .
H18C H 1.0940 0.1050 0.7071 0.042 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
F F 0.0727 0.0534 '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
C17 Sn C18 147.23(8) . .
C17 Sn O1 94.25(7) . .
C18 Sn O1 96.01(6) . .
C17 Sn O2 90.99(6) . .
C18 Sn O2 92.71(6) . .
O1 Sn O2 154.91(5) . .
C17 Sn N1 110.62(7) . .
C18 Sn N1 101.48(7) . .
O1 Sn N1 83.12(5) . .
O2 Sn N1 72.09(5) . .
C1 O1 Sn 132.29(11) . .
C8 O2 Sn 114.13(11) . .
C6 O3 C15 117.7(4) . .
C15' O3' C6 119.3(4) . .
C7 N1 N2 114.39(14) . .
C7 N1 Sn 128.50(12) . .
N2 N1 Sn 116.91(10) . .
C8 N2 N1 111.19(14) . .
O1 C1 C2 124.00(17) . .
O1 C1 C6 119.35(16) . .
C2 C1 C6 116.65(17) . .
C1 C2 C3 120.77(17) . .
C1 C2 C7 124.44(17) . .
C3 C2 C7 114.79(16) . .
C4 C3 C2 121.01(18) . .
C4 C3 H3 119.5 . .
C2 C3 H3 119.5 . .
C3 C4 C5 119.19(18) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
C6 C5 C4 121.05(18) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
O3 C6 C5 123.0(2) . .
O3 C6 C1 114.2(2) . .
C5 C6 C1 121.34(18) . .
C5 C6 O3' 122.6(2) . .
C1 C6 O3' 114.7(2) . .
N1 C7 C2 127.50(16) . .
N1 C7 H7 116.2 . .
C2 C7 H7 116.2 . .
O2 C8 N2 125.27(16) . .
O2 C8 C9 118.25(15) . .
N2 C8 C9 116.45(15) . .
C10 C9 C14 119.10(16) . .
C10 C9 C8 119.94(16) . .
C14 C9 C8 120.90(16) . .
C11 C10 C9 120.79(17) . .
C11 C10 H10 119.6 . .
C9 C10 H10 119.6 . .
C12 C11 C10 118.01(17) . .
C12 C11 H11 121.0 . .
C10 C11 H11 121.0 . .
F1 C12 C11 118.59(16) . .
F1 C12 C13 118.21(16) . .
C11 C12 C13 123.20(17) . .
C12 C13 C14 118.13(17) . .
C12 C13 H13 120.9 . .
C14 C13 H13 120.9 . .
C13 C14 C9 120.74(17) . .
C13 C14 H14 119.6 . .
C9 C14 H14 119.6 . .
O3 C15 C16 111.3(4) . .
O3 C15 H15A 109.4 . .
C16 C15 H15A 109.4 . .
O3 C15 H15B 109.4 . .
C16 C15 H15B 109.4 . .
H15A C15 H15B 108.0 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
O3' C15' C16' 113.4(4) . .
O3' C15' H15C 108.9 . .
C16' C15' H15C 108.9 . .
O3' C15' H15D 108.9 . .
C16' C15' H15D 108.9 . .
H15C C15' H15D 107.7 . .
C15' C16' H16D 109.5 . .
C15' C16' H16E 109.5 . .
H16D C16' H16E 109.5 . .
C15' C16' H16F 109.5 . .
H16D C16' H16F 109.5 . .
H16E C16' H16F 109.5 . .
Sn C17 H17A 109.5 . .
Sn C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
Sn C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
Sn C18 H18A 109.5 . .
Sn C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
Sn C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn C17 2.098(2) .
Sn C18 2.1074(19) .
Sn O1 2.1541(12) .
Sn O2 2.1863(13) .
Sn N1 2.1927(15) .
F1 C12 1.366(2) .
O1 C1 1.323(2) .
O2 C8 1.293(2) .
O3 C6 1.341(5) .
O3 C15 1.446(6) .
O3' C15' 1.443(6) .
O3' C6 1.460(5) .
N1 C7 1.296(2) .
N1 N2 1.399(2) .
N2 C8 1.312(2) .
C1 C2 1.410(2) .
C1 C6 1.427(3) .
C2 C3 1.414(3) .
C2 C7 1.439(2) .
C3 C4 1.368(3) .
C3 H3 0.9500 .
C4 C5 1.397(3) .
C4 H4 0.9500 .
C5 C6 1.377(3) .
C5 H5 0.9500 .
C7 H7 0.9500 .
C8 C9 1.484(2) .
C9 C10 1.391(2) .
C9 C14 1.397(2) .
C10 C11 1.386(3) .
C10 H10 0.9500 .
C11 C12 1.374(3) .
C11 H11 0.9500 .
C12 C13 1.376(3) .
C13 C14 1.381(3) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C16 1.509(6) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C15' C16' 1.510(6) .
C15' H15C 0.9900 .
C15' H15D 0.9900 .
C16' H16D 0.9800 .
C16' H16E 0.9800 .
C16' H16F 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
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
C7 N1 N2 C8 179.90(14) . . . .
Sn N1 N2 C8 4.54(17) . . . .
Sn O1 C1 C2 1.3(3) . . . .
Sn O1 C1 C6 -178.85(13) . . . .
O1 C1 C2 C3 179.75(17) . . . .
C6 C1 C2 C3 -0.1(3) . . . .
O1 C1 C2 C7 -0.3(3) . . . .
C6 C1 C2 C7 179.86(17) . . . .
C1 C2 C3 C4 0.1(3) . . . .
C7 C2 C3 C4 -179.90(17) . . . .
C2 C3 C4 C5 -0.3(3) . . . .
C3 C4 C5 C6 0.6(3) . . . .
C15 O3 C6 C5 7.4(4) . . . .
C15 O3 C6 C1 173.8(3) . . . .
C4 C5 C6 O3 164.9(3) . . . .
C4 C5 C6 C1 -0.7(3) . . . .
C4 C5 C6 O3' -166.8(2) . . . .
O1 C1 C6 O3 13.8(3) . . . .
C2 C1 C6 O3 -166.3(2) . . . .
O1 C1 C6 C5 -179.47(18) . . . .
C2 C1 C6 C5 0.4(3) . . . .
O1 C1 C6 O3' -12.3(3) . . . .
C2 C1 C6 O3' 167.6(2) . . . .
C15' O3' C6 C5 3.0(5) . . . .
C15' O3' C6 C1 -164.0(3) . . . .
N2 N1 C7 C2 -179.49(16) . . . .
Sn N1 C7 C2 -4.8(3) . . . .
C1 C2 C7 N1 2.2(3) . . . .
C3 C2 C7 N1 -177.79(17) . . . .
Sn O2 C8 N2 -5.2(2) . . . .
Sn O2 C8 C9 172.90(11) . . . .
N1 N2 C8 O2 0.5(2) . . . .
N1 N2 C8 C9 -177.63(13) . . . .
O2 C8 C9 C10 -9.4(2) . . . .
N2 C8 C9 C10 168.87(16) . . . .
O2 C8 C9 C14 173.17(16) . . . .
N2 C8 C9 C14 -8.5(2) . . . .
C14 C9 C10 C11 1.2(3) . . . .
C8 C9 C10 C11 -176.20(17) . . . .
C9 C10 C11 C12 -0.6(3) . . . .
C10 C11 C12 F1 179.84(16) . . . .
C10 C11 C12 C13 0.0(3) . . . .
F1 C12 C13 C14 -179.91(16) . . . .
C11 C12 C13 C14 -0.1(3) . . . .
C12 C13 C14 C9 0.7(3) . . . .
C10 C9 C14 C13 -1.3(3) . . . .
C8 C9 C14 C13 176.10(16) . . . .
C6 O3 C15 C16 77.0(4) . . . .
C6 O3' C15' C16' -81.0(4) . . . .
