#------------------------------------------------------------------------------
#$Date: 2021-02-15 11:37:38 +0200 (Mon, 15 Feb 2021) $
#$Revision: 261956 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/03/1560375.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_1560375
loop_
_publ_author_name
'Fukin, Georgy K.'
'Samsonov, Maxim A.'
'Arapova, Alla V.'
'Mazur, Anton S.'
'Artamonova, Tatiana O.'
'Khodorkovskiy, Mikhail A.'
'Vasilyev, Aleksander V.'
_publ_section_title
;
 Experimental and theoretical distribution of electron density and
 thermopolimerization in crystals of Ph 3 Sb(O 2 CCH=CH 2 ) 2 complex
;
_journal_name_full               'Journal of Solid State Chemistry'
_journal_page_first              32
_journal_page_last               39
_journal_paper_doi               10.1016/j.jssc.2017.06.030
_journal_volume                  254
_journal_year                    2017
_chemical_absolute_configuration -
_chemical_formula_moiety         'C24 H21 O4 Sb'
_chemical_formula_sum            'C24 H21 O4 Sb'
_chemical_formula_weight         495.164
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.
_cell_angle_beta                 98.958(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   8.6968(6)
_cell_length_b                   19.9327(13)
_cell_length_c                   12.2232(8)
_cell_measurement_reflns_used    9764
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      53.70
_cell_measurement_theta_min      3.12
_cell_volume                     2093.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'A molecular Viewer for the MoPro charge density program Version 1.0.165'
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Quest (CMOS)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_source         'microfocus tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.01902
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            382490
_diffrn_reflns_theta_full        51.43
_diffrn_reflns_theta_max         51.43
_diffrn_reflns_theta_min         2.582
_exptl_absorpt_coefficient_mu    1.345
_exptl_absorpt_correction_T_max  0.5432
_exptl_absorpt_correction_T_min  0.3813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.29
_refine_diff_density_rms         0.01
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         14876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.000
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'calc w =1/[7.5766*σ²(Fo²)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0328
_refine_ls_wR_factor_ref         0.0331
_reflns_number_gt                14871
_reflns_number_total             15495
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            mmc3.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1560375
loop_
_symmetry_equiv_pos_as_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_type_symbol
_atom_site_label
_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_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb SB1 -0.403209(6) 0.172149(2) 0.276576(4) 0.011787(2) Uani 1 d . . . .
O O1 -0.64551(9) 0.16930(4) 0.21472(7) 0.01606(4) Uani 1 d . . . .
O O2 -0.59783(12) 0.06035(4) 0.24104(8) 0.01944(5) Uani 1 d . . . .
O O3 -0.16076(10) 0.18323(4) 0.33363(7) 0.01681(4) Uani 1 d . . . .
O O4 -0.17644(11) 0.07246(4) 0.33649(8) 0.01827(4) Uani 1 d . . . .
C C1 -0.68813(11) 0.10621(5) 0.20707(7) 0.01583(4) Uani 1 d . . . .
C C2 -0.84876(14) 0.09167(6) 0.15254(10) 0.02118(6) Uani 1 d . . . .
H H2A -0.89478 0.04145 0.15724 0.02541 Uiso 1 d R U . .
C C3 -0.9392(2) 0.13795(12) 0.09728(16) 0.03088(8) Uani 1 d . . . .
H H3A -0.89625 0.18832 0.09176 0.03705 Uiso 1 d R U . .
H H3B -1.05580 0.12546 0.05922 0.03705 Uiso 1 d R U . .
C C4 -0.09890(11) 0.12409(4) 0.35433(7) 0.01509(4) Uani 1 d . . . .
C C5 0.06841(13) 0.12427(6) 0.40221(10) 0.01972(5) Uani 1 d . . . .
H H5A 0.13270 0.17098 0.40659 0.02366 Uiso 1 d R U . .
C C6 0.14164(17) 0.06834(8) 0.43988(13) 0.02540(7) Uani 1 d . . . .
H H6A 0.07988 0.02138 0.43667 0.03048 Uiso 1 d R U . .
H H6B 0.26329 0.07044 0.47438 0.03048 Uiso 1 d R U . .
C C7 -0.41482(11) 0.27778(4) 0.26837(8) 0.01507(5) Uani 1 d . . . .
C C8 -0.30220(15) 0.31563(4) 0.33571(9) 0.01890(6) Uani 1 d . . . .
H H8A -0.21140 0.29066 0.39180 0.02268 Uiso 1 d R U . .
C C9 -0.30684(19) 0.38543(5) 0.33092(12) 0.02344(8) Uani 1 d . . . .
H H9A -0.22050 0.41459 0.38416 0.02813 Uiso 1 d R U . .
C C10 -0.42256(19) 0.41797(5) 0.25786(14) 0.02547(9) Uani 1 d . . . .
H H10A -0.42360 0.47223 0.25320 0.03056 Uiso 1 d R U . .
C C11 -0.53501(19) 0.38018(6) 0.19134(16) 0.02674(9) Uani 1 d . . . .
H H11A -0.62506 0.40569 0.13538 0.03209 Uiso 1 d R U . .
C C12 -0.53297(15) 0.31033(5) 0.19706(11) 0.02132(6) Uani 1 d . . . .
H H12A -0.62264 0.28144 0.14640 0.02558 Uiso 1 d R U . .
C C13 -0.36294(11) 0.13535(4) 0.12152(7) 0.01450(4) Uani 1 d . . . .
C C14 -0.34170(16) 0.06742(5) 0.10114(9) 0.01938(7) Uani 1 d . . . .
H H14A -0.34297 0.03081 0.16646 0.02326 Uiso 1 d R U . .
C C15 -0.31952(19) 0.04720(6) -0.00441(10) 0.02296(8) Uani 1 d . . . .
H H15A -0.30452 -0.00552 -0.02143 0.02755 Uiso 1 d R U . .
C C16 -0.31764(18) 0.09394(7) -0.08855(9) 0.02265(7) Uani 1 d . . . .
H H16A -0.29739 0.07797 -0.16979 0.02719 Uiso 1 d R U . .
C C17 -0.3412(2) 0.16163(7) -0.06813(9) 0.02357(8) Uani 1 d . . . .
H H17A -0.34089 0.19807 -0.13382 0.02828 Uiso 1 d R U . .
C C18 -0.36453(16) 0.18260(5) 0.03695(8) 0.01964(7) Uani 1 d . . . .
H H18A -0.38364 0.23514 0.05293 0.02356 Uiso 1 d R U . .
C C19 -0.44822(11) 0.14688(4) 0.43598(7) 0.01422(4) Uani 1 d . . . .
C C20 -0.52474(16) 0.19653(5) 0.48774(9) 0.02031(7) Uani 1 d . . . .
H H20A -0.55530 0.24380 0.44633 0.02437 Uiso 1 d R U . .
C C21 -0.5607(2) 0.18490(7) 0.59351(11) 0.02442(8) Uani 1 d . . . .
H H21A -0.61901 0.22322 0.63469 0.02930 Uiso 1 d R U . .
C C22 -0.52105(16) 0.12425(7) 0.64627(9) 0.02223(6) Uani 1 d . . . .
H H22A -0.54863 0.11530 0.72843 0.02668 Uiso 1 d R U . .
C C23 -0.44595(15) 0.07473(6) 0.59413(9) 0.02021(6) Uani 1 d . . . .
H H23A -0.41539 0.02754 0.63582 0.02425 Uiso 1 d R U . .
C C24 -0.40968(13) 0.08579(4) 0.48843(8) 0.01690(5) Uani 1 d . . . .
H H24A -0.35199 0.04724 0.44734 0.02028 Uiso 1 d 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 0.0033 0.0016 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
H H 0.0000 0.0000 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
O O 0.0106 0.0060 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
Sb Sb -0.5630 1.5715 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
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_2
_geom_angle_site_symmetry_3
O1 SB1 O3 175.30(3) . . .
O1 SB1 C19 90.34(3) . . .
O1 SB1 C7 88.41(3) . . .
O1 SB1 C13 88.01(3) . . .
O3 SB1 C19 92.24(4) . . .
O3 SB1 C7 87.11(3) . . .
O3 SB1 C13 92.06(3) . . .
C19 SB1 C7 105.55(3) . . .
C19 SB1 C13 145.84(6) . . .
C7 SB1 C13 108.50(3) . . .
C3 C2 H2A 118.358 . . .
H3A C3 H3B 120.056 . . .
C6 C5 H5A 119.185 . . .
H6A C6 H6B 120.129 . . .
C8 C7 C12 119.71(10) . . .
C9 C8 H8A 119.955 . . .
C10 C9 H9A 119.881 . . .
C11 C10 C9 119.54(14) . . .
C11 C10 H10A 120.687 . . .
C12 C11 H11A 120.193 . . .
C14 C13 C18 120.58(9) . . .
C15 C14 H14A 120.424 . . .
C16 C15 C14 120.70(11) . . .
C16 C15 H15A 119.517 . . .
C17 C16 H16A 119.888 . . .
C18 C17 H17A 119.934 . . .
C24 C19 C20 120.54(9) . . .
C21 C20 H20A 120.200 . . .
C22 C21 C20 119.95(11) . . .
C22 C21 H21A 119.917 . . .
C23 C22 H22A 119.687 . . .
C24 C23 H23A 119.936 . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
SB1 O1 2.1258(2) .
SB1 O3 2.1268(3) .
SB1 C19 2.1074(2) .
SB1 C7 2.1095(2) .
SB1 C13 2.1117(2) .
O1 C1 1.3101(5) .
O2 C1 1.2342(6) .
O3 C4 1.3041(5) .
O4 C4 1.2310(5) .
C1 C2 1.4798(5) .
C2 C3 1.3267(9) .
C2 H2A 1.08300 .
C3 H3A 1.07700 .
C3 H3B 1.07700 .
C4 C5 1.4813(5) .
C5 C6 1.3301(7) .
C5 H5A 1.08300 .
C6 H6A 1.07700 .
C6 H6B 1.07700 .
C7 C8 1.3983(5) .
C7 C12 1.3992(5) .
C8 C9 1.3929(5) .
C8 H8A 1.08300 .
C9 C10 1.3967(8) .
C9 H9A 1.08300 .
C10 C11 1.3918(9) .
C10 H10A 1.08300 .
C11 C12 1.3940(6) .
C11 H11A 1.08300 .
C12 H12A 1.08300 .
C13 C14 1.3943(5) .
C13 C18 1.3969(5) .
C14 C15 1.3934(5) .
C14 H14A 1.08300 .
C15 C16 1.3897(7) .
C15 H15A 1.08300 .
C16 C17 1.3930(7) .
C16 H16A 1.08300 .
C17 C18 1.3954(6) .
C17 H17A 1.08300 .
C18 H18A 1.08300 .
C19 C24 1.3925(4) .
C19 C20 1.3976(5) .
C20 C21 1.3962(6) .
C20 H20A 1.08300 .
C21 C22 1.3883(7) .
C21 H21A 1.08300 .
C22 C23 1.3916(7) .
C22 H22A 1.08300 .
C23 C24 1.3943(5) .
C23 H23A 1.08300 .
C24 H24A 1.08300 .
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
C3 H3A C20 1.077 2.773 3.5947(4) 132.95 4_454
C10 H10A O4 1.083 2.500 3.4444(3) 145.15 2_455
C23 H23A O2 1.083 2.301 3.3489(3) 162.31 3_456
C16 H16A C22 1.083 2.886 3.4950(4) 115.74 1_554
C8 H8A O3 1.083 2.320 2.9135(3) 112.63 1_555
C12 H12A O1 1.083 2.405 2.9955(3) 112.75 1_555
C14 H14A O2 1.083 2.592 3.0153(3) 102.33 1_555
C14 H14A O4 1.083 2.484 3.0106(3) 108.66 1_555
C18 H18A C7 1.083 2.820 3.4896(3) 119.97 1_555
C20 H20A C7 1.083 2.741 3.3949(3) 118.60 1_555
C24 H24A O4 1.083 2.250 2.9678(3) 121.84 1_555
C22 H22A C16 1.083 2.797 3.4950(4) 122.11 1_556
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
SB1 O1 C1 O2 . . . . 5.57(6)
SB1 O1 C1 C2 . . . . -172.59(4)
SB1 O3 C4 O4 . . . . 2.85(6)
SB1 O3 C4 C5 . . . . -176.01(2)
SB1 C19 C24 C23 . . . . -179.766(17)
SB1 C19 C24 H24A . . . . 0.24
SB1 C19 C20 C21 . . . . 179.785(17)
SB1 C19 C20 H20A . . . . -0.58
SB1 C7 C8 C9 . . . . 179.433(5)
SB1 C7 C8 H8A . . . . -0.71
SB1 C7 C12 C11 . . . . -178.253(9)
SB1 C7 C12 H12A . . . . 1.74
SB1 C13 C14 C15 . . . . 178.434(14)
SB1 C13 C14 H14A . . . . -1.28
SB1 C13 C18 C17 . . . . -179.015(11)
SB1 C13 C18 H18A . . . . 1.07
O1 SB1 O3 C4 . . . . -163.93(5)
O1 SB1 C19 C24 . . . . 110.73(6)
O1 SB1 C19 C20 . . . . -68.14(8)
O1 SB1 C7 C8 . . . . 156.69(11)
O1 SB1 C7 C12 . . . . -23.23(11)
O1 SB1 C13 C14 . . . . -95.53(7)
O1 SB1 C13 C18 . . . . 81.98(7)
O1 C1 C2 C3 . . . . 10.87(10)
O1 C1 C2 H2A . . . . -169.43
O2 C1 C2 C3 . . . . -167.31(11)
O2 C1 C2 H2A . . . . 12.39
O3 SB1 O1 C1 . . . . 162.38(5)
O3 SB1 C19 C24 . . . . -73.20(6)
O3 SB1 C19 C20 . . . . 107.93(8)
O3 SB1 C7 C8 . . . . -24.74(12)
O3 SB1 C7 C12 . . . . 155.34(10)
O3 SB1 C13 C14 . . . . 89.17(7)
O3 SB1 C13 C18 . . . . -93.32(7)
O3 C4 C5 C6 . . . . 171.65(10)
O3 C4 C5 H5A . . . . -8.42
O4 C4 C5 C6 . . . . -7.19(9)
O4 C4 C5 H5A . . . . 172.73
C1 O1 SB1 C19 . . . . -74.38(6)
C1 O1 SB1 C7 . . . . -179.93(4)
C1 O1 SB1 C13 . . . . 71.49(6)
C1 C2 C3 H3A . . . . -0.58
C1 C2 C3 H3B . . . . -179.55
H2A C2 C3 H3A . . . . 179.72
H2A C2 C3 H3B . . . . 0.74
C4 O3 SB1 C19 . . . . 72.89(6)
C4 O3 SB1 C7 . . . . 178.36(4)
C4 O3 SB1 C13 . . . . -73.21(6)
C4 C5 C6 H6A . . . . -0.34
C4 C5 C6 H6B . . . . -179.81
H5A C5 C6 H6A . . . . 179.73
H5A C5 C6 H6B . . . . 0.27
C7 SB1 C19 C24 . . . . -160.82(5)
C7 SB1 C19 C20 . . . . 20.31(8)
C7 SB1 C13 C14 . . . . 176.81(4)
C7 SB1 C13 C18 . . . . -5.68(6)
C7 C8 C9 C10 . . . . -0.88(8)
C7 C8 C9 H9A . . . . 179.02
C7 C12 C11 C10 . . . . -1.50(8)
C7 C12 C11 H11A . . . . 179.03
C8 C7 SB1 C19 . . . . 66.78(6)
C8 C7 SB1 C13 . . . . -115.95(7)
C8 C7 C12 C11 . . . . 1.83(9)
C8 C7 C12 H12A . . . . -178.18
C8 C9 C10 C11 . . . . 1.21(9)
C8 C9 C10 H10A . . . . -178.48
H8A C8 C7 C12 . . . . 179.20
H8A C8 C9 C10 . . . . 179.27
H8A C8 C9 H9A . . . . -0.84
C9 C8 C7 C12 . . . . -0.65(9)
C9 C10 C11 C12 . . . . 0.00(10)
C9 C10 C11 H11A . . . . 179.45
H9A C9 C10 C11 . . . . -178.68
H9A C9 C10 H10A . . . . 1.63
C10 C11 C12 H12A . . . . 178.51
H10A C10 C11 C12 . . . . 179.67
H10A C10 C11 H11A . . . . -0.86
H11A C11 C12 H12A . . . . -0.96
C12 C7 SB1 C19 . . . . -113.14(8)
C12 C7 SB1 C13 . . . . 64.14(7)
C13 SB1 C19 C24 . . . . 23.78(6)
C13 SB1 C19 C20 . . . . -155.09(10)
C13 C14 C15 C16 . . . . 0.33(7)
C13 C14 C15 H15A . . . . -179.15
C13 C18 C17 C16 . . . . 0.51(7)
C13 C18 C17 H17A . . . . -179.28
C14 C13 SB1 C19 . . . . -7.86(5)
C14 C13 C18 C17 . . . . -1.44(7)
C14 C13 C18 H18A . . . . 178.64
C14 C15 C16 C17 . . . . -1.26(8)
C14 C15 C16 H16A . . . . 178.43
H14A C14 C13 C18 . . . . -178.69
H14A C14 C15 C16 . . . . -179.95
H14A C14 C15 H15A . . . . 0.57
C15 C16 C17 C18 . . . . 0.83(8)
C15 C16 C17 H17A . . . . -179.38
C15 C14 C13 C18 . . . . 1.02(7)
H15A C15 C16 C17 . . . . 178.23
H15A C15 C16 H16A . . . . -2.08
C16 C17 C18 H18A . . . . -179.58
H16A C16 C17 C18 . . . . -178.86
H16A C16 C17 H17A . . . . 0.93
H17A C17 C18 H18A . . . . 0.63
C18 C13 SB1 C19 . . . . 169.65(5)
C19 C24 C23 C22 . . . . 0.44(7)
C19 C24 C23 H23A . . . . -179.41
C19 C20 C21 C22 . . . . -0.25(8)
C19 C20 C21 H21A . . . . 179.40
C20 C19 C24 C23 . . . . -0.95(7)
C20 C19 C24 H24A . . . . 179.05
C20 C21 C22 C23 . . . . -0.25(8)
C20 C21 C22 H22A . . . . 179.79
H20A C20 C19 C24 . . . . -179.50
H20A C20 C21 C22 . . . . -179.89
H20A C20 C21 H21A . . . . -0.24
C21 C22 C23 C24 . . . . 0.16(8)
C21 C22 C23 H23A . . . . -179.98
C21 C20 C19 C24 . . . . 0.86(8)
H21A C21 C22 C23 . . . . -179.91
H21A C21 C22 H22A . . . . 0.14
C22 C23 C24 H24A . . . . -179.56
H22A C22 C23 C24 . . . . -179.89
H22A C22 C23 H23A . . . . -0.03
H23A C23 C24 H24A . . . . 0.59
