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#$Date: 2022-05-06 12:22:52 +0300 (Fri, 06 May 2022) $
#$Revision: 275101 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105168.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_8105168
loop_
_publ_author_name
'Li, Jing-Yang'
'Miao, Bao-Xi'
'Zhao, Yun'
'Zhang, Li-Fang'
_publ_section_title
;
 Crystal structure of 2-benzoylpyrene, C23H14O
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              547
_journal_page_last               549
_journal_paper_doi               10.1515/ncrs-2019-0790
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C23 H14 O'
_chemical_formula_sum            'C23 H14 O'
_chemical_formula_weight         306.34
_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                 104.80(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.931(3)
_cell_length_b                   10.486(2)
_cell_length_c                   23.004(5)
_cell_measurement_reflns_used    3546
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      3.01
_cell_volume                     3015.7(12)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        SAINT-Plus
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX II CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24470
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         3.259
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       Block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0714P)²+0.1545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1375
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4937
_reflns_number_total             6805
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0790_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        3015.6(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105168
_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.
;
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
O1 O 1.02634(10) 0.63596(12) 0.05932(5) 0.0394(3) Uani 1 1 d . . . . .
C1 C 0.89505(13) 0.78178(16) -0.03752(8) 0.0291(4) Uani 1 1 d . . . . .
H1 H 0.9443 0.8331 -0.0112 0.035 Uiso 1 1 calc R U . . .
C2 C 0.84704(14) 0.82490(17) -0.09496(8) 0.0314(4) Uani 1 1 d . . . . .
H2 H 0.8628 0.9058 -0.1069 0.038 Uiso 1 1 calc R U . . .
C3 C 0.77541(13) 0.74734(17) -0.13462(7) 0.0299(4) Uani 1 1 d . . . . .
H3 H 0.7444 0.7757 -0.1735 0.036 Uiso 1 1 calc R U . . .
C4 C 0.74977(13) 0.62796(16) -0.11677(7) 0.0278(4) Uani 1 1 d . . . . .
H4 H 0.7021 0.5760 -0.1437 0.033 Uiso 1 1 calc R U . . .
C5 C 0.79525(12) 0.58588(16) -0.05874(7) 0.0252(3) Uani 1 1 d . . . . .
H5 H 0.7760 0.5070 -0.0463 0.030 Uiso 1 1 calc R U . . .
C6 C 0.86977(12) 0.66146(15) -0.01898(7) 0.0247(3) Uani 1 1 d . . . . .
C7 C 0.93111(13) 0.61109(15) 0.04071(7) 0.0264(4) Uani 1 1 d . . . . .
C8 C 0.87602(12) 0.52903(15) 0.07645(7) 0.0233(3) Uani 1 1 d . . . . .
C9 C 0.93443(12) 0.43320(15) 0.11275(7) 0.0235(3) Uani 1 1 d . . . . .
H9 H 1.0066 0.4227 0.1146 0.028 Uiso 1 1 calc R U . . .
C10 C 0.88560(12) 0.35307(15) 0.14632(7) 0.0221(3) Uani 1 1 d . . . . .
C11 C 0.94133(13) 0.24981(15) 0.18197(7) 0.0258(4) Uani 1 1 d . . . . .
H11 H 1.0134 0.2369 0.1841 0.031 Uiso 1 1 calc R U . . .
C12 C 0.89121(13) 0.17108(15) 0.21247(7) 0.0260(4) Uani 1 1 d . . . . .
H12 H 0.9294 0.1047 0.2349 0.031 Uiso 1 1 calc R U . . .
C13 C 0.78020(12) 0.18766(14) 0.21105(6) 0.0214(3) Uani 1 1 d . . . . .
C14 C 0.72657(14) 0.10623(15) 0.24147(7) 0.0260(4) Uani 1 1 d . . . . .
H14 H 0.7628 0.0375 0.2629 0.031 Uiso 1 1 calc R U . . .
C15 C 0.61980(14) 0.12638(15) 0.24019(7) 0.0280(4) Uani 1 1 d . . . . .
H15 H 0.5853 0.0711 0.2607 0.034 Uiso 1 1 calc R U . . .
C16 C 0.56440(13) 0.22834(15) 0.20850(7) 0.0256(3) Uani 1 1 d . . . . .
H16 H 0.4931 0.2412 0.2082 0.031 Uiso 1 1 calc R U . . .
C17 C 0.61464(12) 0.31231(14) 0.17699(7) 0.0213(3) Uani 1 1 d . . . . .
C18 C 0.55989(12) 0.41852(14) 0.14357(7) 0.0234(3) Uani 1 1 d . . . . .
H18 H 0.4893 0.4347 0.1438 0.028 Uiso 1 1 calc R U . . .
C19 C 0.60890(12) 0.49574(14) 0.11162(7) 0.0227(3) Uani 1 1 d . . . . .
H19 H 0.5712 0.5637 0.0902 0.027 Uiso 1 1 calc R U . . .
C20 C 0.71821(12) 0.47474(14) 0.11011(6) 0.0203(3) Uani 1 1 d . . . . .
C21 C 0.77610(12) 0.37342(13) 0.14490(6) 0.0193(3) Uani 1 1 d . . . . .
C22 C 0.72364(12) 0.29148(14) 0.17779(6) 0.0195(3) Uani 1 1 d . . . . .
C23 C 0.76917(12) 0.54962(14) 0.07546(7) 0.0226(3) Uani 1 1 d . . . . .
H23 H 0.7312 0.6141 0.0514 0.027 Uiso 1 1 calc R U . . .
O2 O 0.39545(9) 0.65809(10) 0.16360(5) 0.0310(3) Uani 1 1 d . . . . .
C24 C 0.19077(13) 0.75655(16) 0.16691(7) 0.0285(4) Uani 1 1 d . . . . .
H24 H 0.1867 0.6809 0.1454 0.034 Uiso 1 1 calc R U . . .
C25 C 0.10214(14) 0.79999(18) 0.18448(8) 0.0358(4) Uani 1 1 d . . . . .
H25 H 0.0384 0.7544 0.1741 0.043 Uiso 1 1 calc R U . . .
C26 C 0.10869(15) 0.91169(17) 0.21756(8) 0.0373(4) Uani 1 1 d . . . . .
H26 H 0.0495 0.9407 0.2296 0.045 Uiso 1 1 calc R U . . .
C27 C 0.20314(16) 0.97979(16) 0.23253(8) 0.0360(4) Uani 1 1 d . . . . .
H27 H 0.2075 1.0540 0.2552 0.043 Uiso 1 1 calc R U . . .
C28 C 0.29164(14) 0.93853(15) 0.21414(7) 0.0294(4) Uani 1 1 d . . . . .
H28 H 0.3545 0.9859 0.2236 0.035 Uiso 1 1 calc R U . . .
C29 C 0.28599(13) 0.82559(15) 0.18135(7) 0.0235(3) Uani 1 1 d . . . . .
C30 C 0.37999(12) 0.77357(14) 0.16249(7) 0.0224(3) Uani 1 1 d . . . . .
C31 C 0.45175(12) 0.86237(14) 0.14061(7) 0.0220(3) Uani 1 1 d . . . . .
C32 C 0.55802(12) 0.82663(14) 0.14633(7) 0.0227(3) Uani 1 1 d . . . . .
H32 H 0.5843 0.7526 0.1672 0.027 Uiso 1 1 calc R U . . .
C33 C 0.62512(12) 0.90006(14) 0.12123(7) 0.0223(3) Uani 1 1 d . . . . .
C34 C 0.73496(13) 0.86572(15) 0.12655(7) 0.0269(4) Uani 1 1 d . . . . .
H34 H 0.7639 0.7952 0.1495 0.032 Uiso 1 1 calc R U . . .
C35 C 0.79679(13) 0.93451(16) 0.09866(7) 0.0295(4) Uani 1 1 d . . . . .
H35 H 0.8672 0.9096 0.1024 0.035 Uiso 1 1 calc R U . . .
C36 C 0.75620(13) 1.04472(15) 0.06350(7) 0.0261(4) Uani 1 1 d . . . . .
C37 C 0.81766(14) 1.11643(16) 0.03352(7) 0.0306(4) Uani 1 1 d . . . . .
H37 H 0.8878 1.0919 0.0361 0.037 Uiso 1 1 calc R U . . .
C38 C 0.77661(14) 1.22294(16) 0.00013(7) 0.0318(4) Uani 1 1 d . . . . .
H38 H 0.8190 1.2688 -0.0196 0.038 Uiso 1 1 calc R U . . .
C39 C 0.67228(14) 1.26176(15) -0.00403(7) 0.0290(4) Uani 1 1 d . . . . .
H39 H 0.6456 1.3340 -0.0263 0.035 Uiso 1 1 calc R U . . .
C40 C 0.60674(13) 1.19341(14) 0.02488(7) 0.0244(3) Uani 1 1 d . . . . .
C41 C 0.49800(14) 1.22880(15) 0.02096(7) 0.0260(4) Uani 1 1 d . . . . .
H41 H 0.4700 1.3013 -0.0007 0.031 Uiso 1 1 calc R U . . .
C42 C 0.43494(13) 1.15951(15) 0.04796(7) 0.0246(3) Uani 1 1 d . . . . .
H42 H 0.3646 1.1847 0.0442 0.030 Uiso 1 1 calc R U . . .
C43 C 0.47546(12) 1.04783(14) 0.08230(6) 0.0208(3) Uani 1 1 d . . . . .
C44 C 0.58303(12) 1.01110(14) 0.08764(6) 0.0214(3) Uani 1 1 d . . . . .
C45 C 0.64898(13) 1.08363(14) 0.05884(7) 0.0228(3) Uani 1 1 d . . . . .
C46 C 0.41177(12) 0.97325(14) 0.10963(7) 0.0225(3) Uani 1 1 d . . . . .
H46 H 0.3417 0.9980 0.1071 0.027 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 0.0033 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
C2 C1 C6 120.23(16) . .
C1 C2 C3 119.88(16) . .
C4 C3 C2 120.40(16) . .
C3 C4 C5 119.93(16) . .
C4 C5 C6 120.21(15) . .
C5 C6 C1 119.31(15) . .
C5 C6 C7 121.15(14) . .
C1 C6 C7 119.25(14) . .
O1 C7 C8 120.65(15) . .
O1 C7 C6 119.73(15) . .
C8 C7 C6 119.60(14) . .
C23 C8 C9 120.22(14) . .
C23 C8 C7 120.88(14) . .
C9 C8 C7 118.87(14) . .
C10 C9 C8 120.74(14) . .
C9 C10 C21 118.98(14) . .
C9 C10 C11 122.52(14) . .
C21 C10 C11 118.49(14) . .
C12 C11 C10 121.32(15) . .
C11 C12 C13 121.52(14) . .
C14 C13 C22 119.03(15) . .
C14 C13 C12 122.39(14) . .
C22 C13 C12 118.58(14) . .
C15 C14 C13 120.97(15) . .
C16 C15 C14 120.38(15) . .
C15 C16 C17 120.74(15) . .
C16 C17 C22 119.07(14) . .
C16 C17 C18 122.34(14) . .
C22 C17 C18 118.59(14) . .
C19 C18 C17 121.33(14) . .
C18 C19 C20 121.32(14) . .
C23 C20 C21 118.90(14) . .
C23 C20 C19 122.45(14) . .
C21 C20 C19 118.65(14) . .
C20 C21 C10 120.14(14) . .
C20 C21 C22 119.68(14) . .
C10 C21 C22 120.17(13) . .
C13 C22 C17 119.79(14) . .
C13 C22 C21 119.87(14) . .
C17 C22 C21 120.33(13) . .
C8 C23 C20 120.92(14) . .
C25 C24 C29 120.39(16) . .
C24 C25 C26 119.88(17) . .
C27 C26 C25 119.98(17) . .
C26 C27 C28 120.60(16) . .
C27 C28 C29 119.75(16) . .
C24 C29 C28 119.39(15) . .
C24 C29 C30 118.42(14) . .
C28 C29 C30 122.17(15) . .
O2 C30 C31 120.78(14) . .
O2 C30 C29 119.65(14) . .
C31 C30 C29 119.53(13) . .
C46 C31 C32 119.98(14) . .
C46 C31 C30 120.86(14) . .
C32 C31 C30 118.86(14) . .
C33 C32 C31 121.00(14) . .
C32 C33 C44 118.99(14) . .
C32 C33 C34 122.19(14) . .
C44 C33 C34 118.80(14) . .
C35 C34 C33 121.04(15) . .
C34 C35 C36 121.48(15) . .
C37 C36 C45 118.33(15) . .
C37 C36 C35 122.73(15) . .
C45 C36 C35 118.93(14) . .
C38 C37 C36 121.53(16) . .
C37 C38 C39 120.23(16) . .
C38 C39 C40 120.81(16) . .
C39 C40 C45 118.80(16) . .
C39 C40 C41 122.68(15) . .
C45 C40 C41 118.52(14) . .
C42 C41 C40 121.81(15) . .
C41 C42 C43 120.80(15) . .
C46 C43 C44 119.16(14) . .
C46 C43 C42 122.05(14) . .
C44 C43 C42 118.79(14) . .
C43 C44 C45 120.31(14) . .
C43 C44 C33 119.92(14) . .
C45 C44 C33 119.77(14) . .
C40 C45 C36 120.30(15) . .
C40 C45 C44 119.76(15) . .
C36 C45 C44 119.93(14) . .
C31 C46 C43 120.90(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.2241(19) .
C1 C2 1.384(2) .
C1 C6 1.397(2) .
C2 C3 1.386(3) .
C3 C4 1.384(2) .
C4 C5 1.386(2) .
C5 C6 1.394(2) .
C6 C7 1.496(2) .
C7 C8 1.491(2) .
C8 C23 1.393(2) .
C8 C9 1.398(2) .
C9 C10 1.396(2) .
C10 C21 1.424(2) .
C10 C11 1.436(2) .
C11 C12 1.351(2) .
C12 C13 1.438(2) .
C13 C14 1.396(2) .
C13 C22 1.421(2) .
C14 C15 1.390(2) .
C15 C16 1.386(2) .
C16 C17 1.401(2) .
C17 C22 1.422(2) .
C17 C18 1.433(2) .
C18 C19 1.355(2) .
C19 C20 1.440(2) .
C20 C23 1.398(2) .
C20 C21 1.422(2) .
C21 C22 1.426(2) .
O2 C30 1.2265(18) .
C24 C25 1.386(2) .
C24 C29 1.393(2) .
C25 C26 1.388(3) .
C26 C27 1.380(3) .
C27 C28 1.387(2) .
C28 C29 1.396(2) .
C29 C30 1.494(2) .
C30 C31 1.490(2) .
C31 C46 1.392(2) .
C31 C32 1.398(2) .
C32 C33 1.391(2) .
C33 C44 1.426(2) .
C33 C34 1.440(2) .
C34 C35 1.354(2) .
C35 C36 1.431(2) .
C36 C37 1.397(2) .
C36 C45 1.423(2) .
C37 C38 1.382(2) .
C38 C39 1.389(2) .
C39 C40 1.401(2) .
C40 C45 1.420(2) .
C40 C41 1.435(2) .
C41 C42 1.355(2) .
C42 C43 1.435(2) .
C43 C46 1.396(2) .
C43 C44 1.418(2) .
C44 C45 1.426(2) .
