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#$Date: 2022-04-05 12:00:48 +0300 (Tue, 05 Apr 2022) $
#$Revision: 274343 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/50/8105031.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_8105031
loop_
_publ_author_name
'Luo, Peng'
'Chittiboyina, Amar G.'
'Wang, Mei'
'Khan, Ikhlas A.'
'Pan, Wei-Gao'
'Wei, Wan-Xing'
_publ_section_title
;
 Crystal structure of
 12-(2-hydroxybenzoyl)benzo[f]pyrido[1,2-a]indole-6,11-dione, C23H13NO4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              105
_journal_page_last               107
_journal_paper_doi               10.1515/ncrs-2019-0524
_journal_volume                  235
_journal_year                    2019
_chemical_formula_moiety         'C23 H13 N O4'
_chemical_formula_sum            'C23 H13 N O4'
_chemical_formula_weight         367.34
_chemical_name_systematic
;
Crystal structure of
 12-(2-hydroxybenzoyl)benzo[f]pyrido[1,2-a]indole-6,11-dione
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 96.266(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6537(6)
_cell_length_b                   5.1315(2)
_cell_length_c                   26.8047(13)
_cell_measurement_reflns_used    2617
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.73
_cell_volume                     1593.37(13)
_computing_cell_refinement       'Bruker SAINT[1]'
_computing_data_collection       'Bruker APEX3[1]'
_computing_data_reduction        'Bruker SAINT[1]'
_computing_molecular_graphics    'SHELXS-97 (Sheldrick, 2008)[2]'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)[3]'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)[3]'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)[2]'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            14398
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.513
_diffrn_reflns_theta_min         1.839
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       lath
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0531
_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)+(0.0765P)²+0.1899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3317
_reflns_number_total             4810
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0524_suppl.cif
_cod_data_source_block           Amar1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105031
_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   0.968
_shelx_estimated_absorpt_t_max   0.997
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 0.56928(11) -0.2702(2) 0.06371(5) 0.0191(3) Uani 1 1 d . . . . .
O2 O 0.39483(10) 0.5568(2) 0.15726(5) 0.0177(3) Uani 1 1 d . . . . .
O3 O 0.09611(11) 0.5444(2) 0.06004(4) 0.0197(3) Uani 1 1 d . . . . .
O4 O -0.00752(11) 0.7681(2) 0.12774(5) 0.0218(3) Uani 1 1 d . . . . .
H4O H 0.010(2) 0.717(4) 0.0973(10) 0.033 Uiso 1 1 d . U . . .
N1 N 0.33258(12) -0.0672(2) 0.03466(5) 0.0134(3) Uani 1 1 d . . . . .
C1 C 0.52921(14) -0.0858(3) 0.08571(6) 0.0138(3) Uani 1 1 d . . . . .
C2 C 0.41347(14) 0.0127(3) 0.07365(6) 0.0135(3) Uani 1 1 d . . . . .
C3 C 0.36254(14) 0.2088(3) 0.09978(6) 0.0139(3) Uani 1 1 d . . . . .
C4 C 0.43211(14) 0.3608(3) 0.13882(6) 0.0133(3) Uani 1 1 d . . . . .
C5 C 0.55334(14) 0.2688(3) 0.15213(6) 0.0132(3) Uani 1 1 d . . . . .
C6 C 0.62359(14) 0.4053(3) 0.18879(6) 0.0154(3) Uani 1 1 d . . . . .
H6 H 0.5926 0.5458 0.2061 0.018 Uiso 1 1 calc R U . . .
C7 C 0.73880(15) 0.3358(3) 0.19995(6) 0.0171(3) Uani 1 1 d . . . . .
H7 H 0.7865 0.4298 0.2248 0.021 Uiso 1 1 calc R U . . .
C8 C 0.78447(15) 0.1301(3) 0.17505(6) 0.0174(3) Uani 1 1 d . . . . .
H8 H 0.8637 0.0856 0.1823 0.021 Uiso 1 1 calc R U . . .
C9 C 0.71445(15) -0.0109(3) 0.13952(6) 0.0161(3) Uani 1 1 d . . . . .
H9 H 0.7455 -0.1554 0.1234 0.019 Uiso 1 1 calc R U . . .
C10 C 0.59931(14) 0.0572(3) 0.12727(6) 0.0136(3) Uani 1 1 d . . . . .
C11 C 0.34066(15) -0.2625(3) -0.00030(6) 0.0153(3) Uani 1 1 d . . . . .
H11 H 0.4077 -0.3687 0.0009 0.018 Uiso 1 1 calc R U . . .
C12 C 0.25092(15) -0.2995(3) -0.03641(6) 0.0166(3) Uani 1 1 d . . . . .
H12 H 0.2547 -0.4353 -0.0603 0.020 Uiso 1 1 calc R U . . .
C13 C 0.15200(15) -0.1385(3) -0.03890(6) 0.0171(3) Uani 1 1 d . . . . .
H13 H 0.0912 -0.1625 -0.0651 0.021 Uiso 1 1 calc R U . . .
C14 C 0.14328(14) 0.0519(3) -0.00369(6) 0.0153(3) Uani 1 1 d . . . . .
H14 H 0.0769 0.1602 -0.0054 0.018 Uiso 1 1 calc R U . . .
C15 C 0.23385(14) 0.0853(3) 0.03506(6) 0.0138(3) Uani 1 1 d . . . . .
C16 C 0.24945(14) 0.2513(3) 0.07717(6) 0.0138(3) Uani 1 1 d . . . . .
C17 C 0.15555(14) 0.4160(3) 0.09268(6) 0.0133(3) Uani 1 1 d . . . . .
C18 C 0.12771(13) 0.4131(3) 0.14494(6) 0.0127(3) Uani 1 1 d . . . . .
C19 C 0.04765(14) 0.5944(3) 0.16008(6) 0.0141(3) Uani 1 1 d . . . . .
C20 C 0.02286(14) 0.6000(3) 0.21010(6) 0.0165(3) Uani 1 1 d . . . . .
H20 H -0.0274 0.7294 0.2208 0.020 Uiso 1 1 calc R U . . .
C21 C 0.07135(14) 0.4179(3) 0.24362(6) 0.0159(3) Uani 1 1 d . . . . .
H21 H 0.0536 0.4215 0.2774 0.019 Uiso 1 1 calc R U . . .
C22 C 0.14633(14) 0.2279(3) 0.22882(6) 0.0156(3) Uani 1 1 d . . . . .
H22 H 0.1778 0.1001 0.2521 0.019 Uiso 1 1 calc R U . . .
C23 C 0.17427(14) 0.2274(3) 0.18005(6) 0.0141(3) Uani 1 1 d . . . . .
H23 H 0.2259 0.0991 0.1700 0.017 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'
N N 0.0061 0.0033 '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
C19 O4 H4O 104.1(15) . .
C11 N1 C2 129.23(14) . .
C11 N1 C15 122.02(14) . .
C2 N1 C15 108.75(13) . .
O1 C1 C2 123.69(15) . .
O1 C1 C10 121.78(15) . .
C2 C1 C10 114.53(14) . .
N1 C2 C3 107.41(14) . .
N1 C2 C1 127.25(14) . .
C3 C2 C1 125.34(15) . .
C2 C3 C16 109.01(14) . .
C2 C3 C4 120.44(14) . .
C16 C3 C4 129.81(14) . .
O2 C4 C3 122.04(15) . .
O2 C4 C5 122.14(15) . .
C3 C4 C5 115.72(14) . .
C6 C5 C10 119.66(15) . .
C6 C5 C4 118.39(14) . .
C10 C5 C4 121.88(14) . .
C7 C6 C5 120.08(15) . .
C7 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
C8 C7 C6 120.30(16) . .
C8 C7 H7 119.9 . .
C6 C7 H7 119.9 . .
C7 C8 C9 119.97(16) . .
C7 C8 H8 120.0 . .
C9 C8 H8 120.0 . .
C8 C9 C10 120.72(15) . .
C8 C9 H9 119.6 . .
C10 C9 H9 119.6 . .
C9 C10 C5 119.24(15) . .
C9 C10 C1 119.07(14) . .
C5 C10 C1 121.58(14) . .
C12 C11 N1 118.71(15) . .
C12 C11 H11 120.6 . .
N1 C11 H11 120.6 . .
C11 C12 C13 120.79(16) . .
C11 C12 H12 119.6 . .
C13 C12 H12 119.6 . .
C14 C13 C12 120.38(16) . .
C14 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C13 C14 C15 119.28(16) . .
C13 C14 H14 120.4 . .
C15 C14 H14 120.4 . .
N1 C15 C14 118.63(14) . .
N1 C15 C16 108.13(14) . .
C14 C15 C16 133.23(15) . .
C3 C16 C15 106.51(14) . .
C3 C16 C17 130.97(15) . .
C15 C16 C17 122.40(15) . .
O3 C17 C18 120.73(14) . .
O3 C17 C16 118.54(15) . .
C18 C17 C16 120.58(14) . .
C23 C18 C19 118.32(15) . .
C23 C18 C17 122.31(14) . .
C19 C18 C17 119.30(14) . .
O4 C19 C20 117.72(14) . .
O4 C19 C18 122.21(15) . .
C20 C19 C18 120.07(15) . .
C21 C20 C19 119.89(15) . .
C21 C20 H20 120.1 . .
C19 C20 H20 120.1 . .
C20 C21 C22 120.97(15) . .
C20 C21 H21 119.5 . .
C22 C21 H21 119.5 . .
C23 C22 C21 119.33(15) . .
C23 C22 H22 120.3 . .
C21 C22 H22 120.3 . .
C22 C23 C18 121.23(15) . .
C22 C23 H23 119.4 . .
C18 C23 H23 119.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2335(19) .
O2 C4 1.2213(19) .
O3 C17 1.2438(19) .
O4 C19 1.3555(19) .
O4 H4O 0.90(3) .
N1 C11 1.382(2) .
N1 C2 1.391(2) .
N1 C15 1.393(2) .
C1 C2 1.444(2) .
C1 C10 1.499(2) .
C2 C3 1.395(2) .
C3 C16 1.406(2) .
C3 C4 1.475(2) .
C4 C5 1.495(2) .
C5 C6 1.397(2) .
C5 C10 1.410(2) .
C6 C7 1.390(2) .
C6 H6 0.9500 .
C7 C8 1.386(2) .
C7 H7 0.9500 .
C8 C9 1.388(2) .
C8 H8 0.9500 .
C9 C10 1.391(2) .
C9 H9 0.9500 .
C11 C12 1.359(2) .
C11 H11 0.9500 .
C12 C13 1.414(2) .
C12 H12 0.9500 .
C13 C14 1.370(2) .
C13 H13 0.9500 .
C14 C15 1.408(2) .
C14 H14 0.9500 .
C15 C16 1.410(2) .
C16 C17 1.478(2) .
C17 C18 1.472(2) .
C18 C23 1.406(2) .
C18 C19 1.408(2) .
C19 C20 1.402(2) .
C20 C21 1.374(2) .
C20 H20 0.9500 .
C21 C22 1.396(2) .
C21 H21 0.9500 .
C22 C23 1.381(2) .
C22 H22 0.9500 .
C23 H23 0.9500 .
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
O4 H4O O3 0.90(3) 1.73(3) 2.5591(18) 151(2) .
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
C11 N1 C2 C3 -177.28(15) . . . .
C15 N1 C2 C3 2.56(18) . . . .
C11 N1 C2 C1 2.7(3) . . . .
C15 N1 C2 C1 -177.47(15) . . . .
O1 C1 C2 N1 -4.5(3) . . . .
C10 C1 C2 N1 174.66(14) . . . .
O1 C1 C2 C3 175.44(16) . . . .
C10 C1 C2 C3 -5.4(2) . . . .
N1 C2 C3 C16 0.14(18) . . . .
C1 C2 C3 C16 -179.83(15) . . . .
N1 C2 C3 C4 -170.97(13) . . . .
C1 C2 C3 C4 9.1(2) . . . .
C2 C3 C4 O2 169.27(15) . . . .
C16 C3 C4 O2 0.2(3) . . . .
C2 C3 C4 C5 -7.2(2) . . . .
C16 C3 C4 C5 -176.24(15) . . . .
O2 C4 C5 C6 3.4(2) . . . .
C3 C4 C5 C6 179.86(14) . . . .
O2 C4 C5 C10 -173.81(15) . . . .
C3 C4 C5 C10 2.7(2) . . . .
C10 C5 C6 C7 1.3(2) . . . .
C4 C5 C6 C7 -175.98(14) . . . .
C5 C6 C7 C8 -0.4(2) . . . .
C6 C7 C8 C9 -1.3(2) . . . .
C7 C8 C9 C10 2.2(2) . . . .
C8 C9 C10 C5 -1.3(2) . . . .
C8 C9 C10 C1 174.97(15) . . . .
C6 C5 C10 C9 -0.4(2) . . . .
C4 C5 C10 C9 176.71(14) . . . .
C6 C5 C10 C1 -176.58(15) . . . .
C4 C5 C10 C1 0.6(2) . . . .
O1 C1 C10 C9 3.5(2) . . . .
C2 C1 C10 C9 -175.70(14) . . . .
O1 C1 C10 C5 179.64(15) . . . .
C2 C1 C10 C5 0.4(2) . . . .
C2 N1 C11 C12 -177.71(16) . . . .
C15 N1 C11 C12 2.5(2) . . . .
N1 C11 C12 C13 1.2(2) . . . .
C11 C12 C13 C14 -2.4(3) . . . .
C12 C13 C14 C15 -0.1(2) . . . .
C11 N1 C15 C14 -4.9(2) . . . .
C2 N1 C15 C14 175.23(14) . . . .
C11 N1 C15 C16 175.57(14) . . . .
C2 N1 C15 C16 -4.28(17) . . . .
C13 C14 C15 N1 3.6(2) . . . .
C13 C14 C15 C16 -177.01(17) . . . .
C2 C3 C16 C15 -2.72(18) . . . .
C4 C3 C16 C15 167.29(16) . . . .
C2 C3 C16 C17 173.16(16) . . . .
C4 C3 C16 C17 -16.8(3) . . . .
N1 C15 C16 C3 4.27(17) . . . .
C14 C15 C16 C3 -175.14(17) . . . .
N1 C15 C16 C17 -172.05(14) . . . .
C14 C15 C16 C17 8.5(3) . . . .
C3 C16 C17 O3 138.38(18) . . . .
C15 C16 C17 O3 -46.3(2) . . . .
C3 C16 C17 C18 -46.0(2) . . . .
C15 C16 C17 C18 129.34(17) . . . .
O3 C17 C18 C23 164.88(15) . . . .
C16 C17 C18 C23 -10.7(2) . . . .
O3 C17 C18 C19 -12.1(2) . . . .
C16 C17 C18 C19 172.34(15) . . . .
C23 C18 C19 O4 -175.26(15) . . . .
C17 C18 C19 O4 1.9(2) . . . .
C23 C18 C19 C20 4.9(2) . . . .
C17 C18 C19 C20 -177.97(15) . . . .
O4 C19 C20 C21 176.16(15) . . . .
C18 C19 C20 C21 -4.0(2) . . . .
C19 C20 C21 C22 0.7(3) . . . .
C20 C21 C22 C23 1.6(2) . . . .
C21 C22 C23 C18 -0.6(2) . . . .
C19 C18 C23 C22 -2.6(2) . . . .
C17 C18 C23 C22 -179.64(15) . . . .
