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#$Date: 2022-06-13 10:14:23 +0300 (Mon, 13 Jun 2022) $
#$Revision: 275978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105384.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_8105384
loop_
_publ_author_name
'Guo, Chun-Mei'
'Song, Xiu-Ying'
'Wang, Mi-Na'
'Gu, Jia'
'Nie, Xu-Liang'
_publ_section_title
;
 Crystal structure of 3-cinnamoyl-4-hydroxybenzoic acid, C16H12O4
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1083
_journal_page_last               1085
_journal_paper_doi               10.1515/ncrs-2020-0178
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C16 H12 O4'
_chemical_formula_sum            'C16 H12 O4'
_chemical_formula_weight         268.26
_chemical_name_common
;
3-cinnamoyl-4-hydroxybenzoic acid
;
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.331(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.760(5)
_cell_length_b                   4.9003(18)
_cell_length_c                   19.125(7)
_cell_measurement_reflns_used    2907
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.90
_cell_measurement_theta_min      3.02
_cell_volume                     1264.4(8)
_computing_cell_refinement       'APEX2, SAINT and SADABS [1]'
_computing_data_collection       'APEX2, SAINT and SADABS [1]'
_computing_data_reduction        'APEX2, SAINT and SADABS [1]'
_computing_molecular_graphics    'Diamond 4.0 [3]'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014) [2]'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014) [2]'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014) [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9086
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.172
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_transmission_factor_max   0.984
_exptl_transmission_factor_min   0.978
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Crystallogr. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0574P)²+0.0989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1072
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1731
_reflns_number_total             2343
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0178_suppl.cif
_cod_data_source_block           3966_0m
_cod_original_cell_volume        1264.5(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105384
_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   0.978
_shelx_estimated_absorpt_t_max   0.984
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
C1 C 0.77919(10) 0.6380(3) 1.06311(8) 0.0397(4) Uani 1 1 d . . . . .
C2 C 0.78315(11) 0.5818(3) 1.13623(8) 0.0416(4) Uani 1 1 d . . . . .
C3 C 0.72342(12) 0.7273(3) 1.17403(8) 0.0468(4) Uani 1 1 d . . . . .
H3 H 0.7258 0.6886 1.2219 0.056 Uiso 1 1 calc R U . . .
C4 C 0.66175(11) 0.9255(3) 1.14138(8) 0.0444(4) Uani 1 1 d . . . . .
H4 H 0.6222 1.0207 1.1673 0.053 Uiso 1 1 calc R U . . .
C5 C 0.65682(10) 0.9887(3) 1.06928(8) 0.0387(4) Uani 1 1 d . . . . .
C6 C 0.71519(10) 0.8435(3) 1.03136(8) 0.0392(4) Uani 1 1 d . . . . .
H6 H 0.7118 0.8838 0.9834 0.047 Uiso 1 1 calc R U . . .
C7 C 0.58925(10) 1.2080(3) 1.03728(8) 0.0390(4) Uani 1 1 d . . . . .
C8 C 0.84122(11) 0.4732(3) 1.02408(9) 0.0454(4) Uani 1 1 d . . . . .
C9 C 0.83713(12) 0.5112(4) 0.94729(9) 0.0504(4) Uani 1 1 d . . . . .
H9 H 0.7958 0.6439 0.9225 0.060 Uiso 1 1 calc R U . . .
C10 C 0.89186(12) 0.3578(4) 0.91312(9) 0.0512(4) Uani 1 1 d . . . . .
H10 H 0.9311 0.2280 0.9408 0.061 Uiso 1 1 calc R U . . .
C11 C 0.89932(12) 0.3637(4) 0.83814(9) 0.0493(4) Uani 1 1 d . . . . .
C12 C 0.96149(13) 0.1802(4) 0.81336(11) 0.0630(5) Uani 1 1 d . . . . .
H12 H 0.9973 0.0546 0.8447 0.076 Uiso 1 1 calc R U . . .
C13 C 0.97090(15) 0.1813(4) 0.74304(12) 0.0709(6) Uani 1 1 d . . . . .
H13 H 1.0131 0.0572 0.7274 0.085 Uiso 1 1 calc R U . . .
C14 C 0.91873(14) 0.3629(4) 0.69604(11) 0.0667(6) Uani 1 1 d . . . . .
H14 H 0.9252 0.3626 0.6486 0.080 Uiso 1 1 calc R U . . .
C15 C 0.85659(14) 0.5462(5) 0.71923(10) 0.0677(5) Uani 1 1 d . . . . .
H15 H 0.8209 0.6704 0.6874 0.081 Uiso 1 1 calc R U . . .
C16 C 0.84680(14) 0.5470(4) 0.78955(10) 0.0617(5) Uani 1 1 d . . . . .
H16 H 0.8044 0.6719 0.8047 0.074 Uiso 1 1 calc R U . . .
O1 O 0.58625(8) 1.2546(2) 0.96936(5) 0.0502(3) Uani 1 1 d . . . . .
H1 H 0.5453 1.3741 0.9554 0.075 Uiso 1 1 calc R U . . .
O2 O 0.53939(8) 1.3372(2) 1.07233(6) 0.0496(3) Uani 1 1 d . . . . .
O3 O 0.84206(8) 0.3900(2) 1.17154(6) 0.0547(3) Uani 1 1 d . . . . .
H3A H 0.8760 0.3230 1.1452 0.082 Uiso 1 1 calc R U . . .
O4 O 0.89718(9) 0.2970(3) 1.05631(6) 0.0614(4) Uani 1 1 d . . . . .
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
C6 C1 C2 117.95(14) . .
C6 C1 C8 123.48(14) . .
C2 C1 C8 118.57(14) . .
O3 C2 C3 117.36(14) . .
O3 C2 C1 122.59(14) . .
C3 C2 C1 120.05(15) . .
C4 C3 C2 120.44(15) . .
C3 C4 C5 121.01(15) . .
C6 C5 C4 118.83(15) . .
C6 C5 C7 122.85(14) . .
C4 C5 C7 118.32(13) . .
C5 C6 C1 121.71(14) . .
O2 C7 O1 122.69(14) . .
O2 C7 C5 121.68(14) . .
O1 C7 C5 115.64(13) . .
O4 C8 C9 118.93(14) . .
O4 C8 C1 119.58(15) . .
C9 C8 C1 121.49(15) . .
C10 C9 C8 120.49(17) . .
C9 C10 C11 129.14(17) . .
C12 C11 C16 117.72(17) . .
C12 C11 C10 119.38(17) . .
C16 C11 C10 122.90(15) . .
C13 C12 C11 120.94(19) . .
C14 C13 C12 120.52(18) . .
C13 C14 C15 119.64(19) . .
C14 C15 C16 120.3(2) . .
C15 C16 C11 120.92(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.396(2) .
C1 C2 1.416(2) .
C1 C8 1.479(2) .
C2 O3 1.3345(18) .
C2 C3 1.393(2) .
C3 C4 1.358(2) .
C4 C5 1.402(2) .
C5 C6 1.380(2) .
C5 C7 1.473(2) .
C7 O2 1.2252(17) .
C7 O1 1.3115(18) .
C8 O4 1.2376(19) .
C8 C9 1.470(2) .
C9 C10 1.324(2) .
C10 C11 1.458(2) .
C11 C12 1.387(2) .
C11 C16 1.389(3) .
C12 C13 1.376(3) .
C13 C14 1.365(3) .
C14 C15 1.372(3) .
C15 C16 1.378(3) .
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
O3 H3A O4 0.82 1.78 2.5093(18) 146.5 .
O1 H1 O2 0.82 1.84 2.6618(17) 175.4 3_687
C3 H3 O3 0.93 2.60 3.349(2) 138.3 2_657
