#------------------------------------------------------------------------------
#$Date: 2022-04-03 23:19:51 +0300 (Sun, 03 Apr 2022) $
#$Revision: 274274 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/94/4519423.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_4519423
loop_
_publ_author_name
'Fomina, Marina V.'
'Vatsadze, Sergey Z.'
'Freidzon, Alexandra Ya.'
'Kuz’mina, Lyudmila G.'
'Moiseeva, Anna A.'
'Starostin, Roman O.'
'Nuriev, Vyacheslav N.'
'Gromov, Sergey P.'
_publ_section_title
;
 Structure--Property Relationships of Dibenzylidenecyclohexanones
;
_journal_issue                   12
_journal_name_full               'ACS Omega'
_journal_page_first              10087
_journal_page_last               10099
_journal_paper_doi               10.1021/acsomega.1c06129
_journal_volume                  7
_journal_year                    2022
_chemical_formula_moiety         'C20 H18 O'
_chemical_formula_sum            'C20 H18 O'
_chemical_formula_weight         274.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 115.2690(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4669(3)
_cell_length_b                   18.2488(7)
_cell_length_c                   9.3371(3)
_cell_measurement_reflns_used    6091
_cell_measurement_temperature    170.15
_cell_measurement_theta_max      30.468
_cell_measurement_theta_min      2.232
_cell_volume                     1458.72(9)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14940
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.38
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6746
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0445 before and 0.0360 after correction.
The Ratio of minimum to maximum transmission is 0.9042.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0645P)²+0.2314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                3227
_reflns_number_total             3830
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao1c06129_si_001.cif
_cod_data_source_block           p21c
_cod_database_code               4519423
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C7A(H7A), C9A(H9A),
 C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.39680(9) 0.61504(4) 0.09266(9) 0.02740(18) Uani 1 d . . .
C1 C 0.32625(11) 0.55832(5) 0.03232(11) 0.02070(19) Uani 1 d . . .
C2 C 0.17359(11) 0.56196(5) -0.11191(11) 0.02054(19) Uani 1 d . . .
C3 C 0.11223(12) 0.49267(5) -0.20565(12) 0.0247(2) Uani 1 d . . .
H3A H 0.1667 0.4837 -0.2739 0.030 Uiso 1 calc . . R
H3B H -0.0007 0.4981 -0.2747 0.030 Uiso 1 calc . . R
C4 C 0.13808(12) 0.42771(6) -0.09371(13) 0.0265(2) Uani 1 d . . .
H4A H 0.0817 0.4365 -0.0271 0.032 Uiso 1 calc . . R
H4B H 0.0949 0.3828 -0.1566 0.032 Uiso 1 calc . . R
C5 C 0.31129(11) 0.41651(5) 0.01244(12) 0.0235(2) Uani 1 d . . .
H5A H 0.3231 0.3767 0.0889 0.028 Uiso 1 calc . . R
H5B H 0.3645 0.4008 -0.0535 0.028 Uiso 1 calc . . R
C6 C 0.38953(11) 0.48479(5) 0.10250(11) 0.02041(19) Uani 1 d . . .
C7 C 0.09907(12) 0.62675(5) -0.14117(12) 0.0229(2) Uani 1 d . . .
H7 H 0.1481 0.6640 -0.0649 0.027 Uiso 1 calc . . R
C8 C -0.04788(12) 0.64790(5) -0.27488(12) 0.0225(2) Uani 1 d . . .
C9 C -0.08794(13) 0.62428(6) -0.43018(12) 0.0257(2) Uani 1 d . . .
H9 H -0.0190 0.5932 -0.4520 0.031 Uiso 1 calc . . R
C10 C -0.22833(13) 0.64618(6) -0.55244(13) 0.0289(2) Uani 1 d . . .
H10 H -0.2544 0.6301 -0.6575 0.035 Uiso 1 calc . . R
C11 C -0.33058(13) 0.69123(6) -0.52263(13) 0.0299(2) Uani 1 d . . .
H11 H -0.4280 0.7045 -0.6061 0.036 Uiso 1 calc . . R
C12 C -0.28999(13) 0.71694(6) -0.37019(14) 0.0305(2) Uani 1 d . . .
H12 H -0.3586 0.7487 -0.3495 0.037 Uiso 1 calc . . R
C13 C -0.14876(13) 0.69610(6) -0.24768(13) 0.0273(2) Uani 1 d . . .
H13 H -0.1204 0.7149 -0.1441 0.033 Uiso 1 calc . . R
C7A C 0.51056(12) 0.48640(5) 0.24711(12) 0.0227(2) Uani 1 d . . .
H7A H 0.5455 0.5341 0.2876 0.027 Uiso 1 calc . . R
C8A C 0.59699(11) 0.42607(5) 0.35196(12) 0.0224(2) Uani 1 d . . .
C9A C 0.61563(12) 0.35615(6) 0.30020(12) 0.0250(2) Uani 1 d . . .
H9A H 0.5738 0.3458 0.1900 0.030 Uiso 1 calc . . R
C10A C 0.69506(13) 0.30183(6) 0.40942(13) 0.0303(2) Uani 1 d . . .
H10A H 0.7064 0.2544 0.3735 0.036 Uiso 1 calc . . R
C11A C 0.75798(13) 0.31652(7) 0.57099(13) 0.0315(2) Uani 1 d . . .
H11A H 0.8103 0.2789 0.6452 0.038 Uiso 1 calc . . R
C12A C 0.74430(13) 0.38599(6) 0.62367(12) 0.0293(2) Uani 1 d . . .
H12A H 0.7883 0.3963 0.7339 0.035 Uiso 1 calc . . R
C13A C 0.66627(12) 0.44042(6) 0.51512(12) 0.0261(2) Uani 1 d . . .
H13A H 0.6596 0.4883 0.5519 0.031 Uiso 1 calc . . R
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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
O1 C1 C2 120.07(9) . . ?
O1 C1 C6 120.97(9) . . ?
C2 C1 C6 118.95(8) . . ?
C1 C2 C3 118.02(8) . . ?
C7 C2 C1 116.30(8) . . ?
C7 C2 C3 125.57(9) . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C2 C3 C4 110.13(8) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 C3 111.22(8) . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 112.80(8) . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C1 C6 C5 119.04(8) . . ?
C7A C6 C1 115.34(9) . . ?
C7A C6 C5 125.56(9) . . ?
C2 C7 H7 115.5 . . ?
C2 C7 C8 128.92(9) . . ?
C8 C7 H7 115.5 . . ?
C9 C8 C7 122.57(9) . . ?
C13 C8 C7 118.87(9) . . ?
C13 C8 C9 118.50(9) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.19(10) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.69(10) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.68(10) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.93(10) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 120.90(10) . . ?
C12 C13 H13 119.5 . . ?
C6 C7A H7A 114.9 . . ?
C6 C7A C8A 130.17(9) . . ?
C8A C7A H7A 114.9 . . ?
C9A C8A C7A 124.67(9) . . ?
C9A C8A C13A 118.36(9) . . ?
C13A C8A C7A 116.96(9) . . ?
C8A C9A H9A 119.9 . . ?
C10A C9A C8A 120.28(10) . . ?
C10A C9A H9A 119.9 . . ?
C9A C10A H10A 119.8 . . ?
C9A C10A C11A 120.34(10) . . ?
C11A C10A H10A 119.8 . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A C10A 119.97(10) . . ?
C12A C11A H11A 120.0 . . ?
C11A C12A H12A 120.1 . . ?
C11A C12A C13A 119.84(10) . . ?
C13A C12A H12A 120.1 . . ?
C8A C13A H13A 119.4 . . ?
C12A C13A C8A 121.12(10) . . ?
C12A C13A H13A 119.4 . . ?
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
O1 C1 1.2303(12) . ?
C1 C2 1.4983(13) . ?
C1 C6 1.5013(13) . ?
C2 C3 1.5061(13) . ?
C2 C7 1.3437(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5295(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5249(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5088(13) . ?
C6 C7A 1.3476(13) . ?
C7 H7 0.9500 . ?
C7 C8 1.4698(13) . ?
C8 C9 1.4009(14) . ?
C8 C13 1.3991(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.3906(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3858(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3881(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3910(15) . ?
C13 H13 0.9500 . ?
C7A H7A 0.9500 . ?
C7A C8A 1.4683(13) . ?
C8A C9A 1.4020(14) . ?
C8A C13A 1.4024(14) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.3904(14) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.3912(16) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.3857(16) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.3857(15) . ?
C13A H13A 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
_geom_torsion_publ_flag
O1 C1 C2 C3 164.56(9) . . . . ?
O1 C1 C2 C7 -18.94(14) . . . . ?
O1 C1 C6 C5 -171.60(9) . . . . ?
O1 C1 C6 C7A 11.01(14) . . . . ?
C1 C2 C3 C4 41.38(12) . . . . ?
C1 C2 C7 C8 177.51(10) . . . . ?
C1 C6 C7A C8A 177.77(10) . . . . ?
C2 C1 C6 C5 9.33(13) . . . . ?
C2 C1 C6 C7A -168.06(9) . . . . ?
C2 C3 C4 C5 -60.52(11) . . . . ?
C2 C7 C8 C9 -38.71(17) . . . . ?
C2 C7 C8 C13 144.23(11) . . . . ?
C3 C2 C7 C8 -6.29(17) . . . . ?
C3 C4 C5 C6 54.24(12) . . . . ?
C4 C5 C6 C1 -28.32(13) . . . . ?
C4 C5 C6 C7A 148.79(10) . . . . ?
C5 C6 C7A C8A 0.57(18) . . . . ?
C6 C1 C2 C3 -16.36(13) . . . . ?
C6 C1 C2 C7 160.13(9) . . . . ?
C6 C7A C8A C9A 28.17(17) . . . . ?
C6 C7A C8A C13A -152.38(11) . . . . ?
C7 C2 C3 C4 -134.75(11) . . . . ?
C7 C8 C9 C10 -179.76(10) . . . . ?
C7 C8 C13 C12 -179.20(10) . . . . ?
C8 C9 C10 C11 -0.27(16) . . . . ?
C9 C8 C13 C12 3.62(16) . . . . ?
C9 C10 C11 C12 2.36(16) . . . . ?
C10 C11 C12 C13 -1.43(17) . . . . ?
C11 C12 C13 C8 -1.58(17) . . . . ?
C13 C8 C9 C10 -2.68(15) . . . . ?
C7A C8A C9A C10A -177.70(10) . . . . ?
C7A C8A C13A C12A 177.12(10) . . . . ?
C8A C9A C10A C11A -0.58(16) . . . . ?
C9A C8A C13A C12A -3.40(15) . . . . ?
C9A C10A C11A C12A -1.28(17) . . . . ?
C10A C11A C12A C13A 0.77(17) . . . . ?
C11A C12A C13A C8A 1.60(16) . . . . ?
C13A C8A C9A C10A 2.87(15) . . . . ?
