#------------------------------------------------------------------------------
#$Date: 2023-07-06 21:17:42 +0300 (Thu, 06 Jul 2023) $
#$Revision: 285049 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022759.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022759
loop_
_publ_author_name
'Hong, Dabeen'
'Lee, Kyounghoon'
_publ_section_title
;
 Polymorphic structures of
 3-phenyl-1H-1,3-benzo-diazol-2(3H)-one.
;
_journal_coeditor_code           VM2281
_journal_issue                   'Pt 6'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              534
_journal_page_last               537
_journal_paper_doi               10.1107/S2056989023003961
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C13 H10 N2 O'
_chemical_formula_moiety         'C13 H10 N2 O'
_chemical_formula_sum            'C13 H10 N2 O'
_chemical_formula_weight         210.23
_chemical_name_systematic
;
3-Phenyl-1H-1,3-benzodiazol-2(3H)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.181(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.0187(9)
_cell_length_b                   6.4455(3)
_cell_length_c                   18.7315(10)
_cell_measurement_reflns_used    2753
_cell_measurement_temperature    193.15
_cell_measurement_theta_max      27.505
_cell_measurement_theta_min      2.332
_cell_volume                     2028.50(18)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
Olex2 1.3 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.3 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      193.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9328
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.579
_diffrn_reflns_theta_min         2.332
_diffrn_source_current           18.0
_diffrn_source_power             0.9
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.226
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0407
_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)+(0.0438P)²+1.4081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                1956
_reflns_number_total             2350
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2281sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2022759--2022760.cif.'
_cod_database_code               2022759
_cod_database_fobs_code          2022759
_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   0.956
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.60223(5) 0.96614(15) 0.57745(5) 0.0239(2) Uani d 1 . .
N N3 0.53005(6) 0.77512(18) 0.46886(6) 0.0210(3) Uani d 1 . .
H H3 0.488955 0.857863 0.448435 0.025 Uiso calc 1 . .
N N1 0.64477(6) 0.64976(18) 0.54578(6) 0.0199(3) Uani d 1 . .
C C8 0.71782(7) 0.6314(2) 0.60949(7) 0.0200(3) Uani d 1 . .
C C7A 0.61292(7) 0.5048(2) 0.48703(7) 0.0198(3) Uani d 1 . .
C C3A 0.54019(7) 0.5865(2) 0.43844(7) 0.0202(3) Uani d 1 . .
C C2 0.59267(7) 0.8152(2) 0.53505(7) 0.0201(3) Uani d 1 . .
C C9 0.73216(8) 0.4585(2) 0.65660(7) 0.0242(3) Uani d 1 . .
H H9 0.694564 0.348538 0.645522 0.029 Uiso calc 1 . .
C C13 0.77316(7) 0.7904(2) 0.62403(7) 0.0230(3) Uani d 1 . .
H H13 0.763240 0.907155 0.590917 0.028 Uiso calc 1 . .
C C7 0.64074(8) 0.3170(2) 0.47242(8) 0.0236(3) Uani d 1 . .
H H7 0.689738 0.261391 0.506014 0.028 Uiso calc 1 . .
C C4 0.49365(8) 0.4809(2) 0.37362(7) 0.0238(3) Uani d 1 . .
H H4 0.443989 0.534926 0.340804 0.029 Uiso calc 1 . .
C C5 0.52220(8) 0.2924(2) 0.35821(8) 0.0274(3) Uani d 1 . .
H H5 0.491700 0.217059 0.313667 0.033 Uiso calc 1 . .
C C10 0.80220(8) 0.4481(2) 0.72020(8) 0.0275(3) Uani d 1 . .
H H10 0.812386 0.330940 0.753147 0.033 Uiso calc 1 . .
C C6 0.59439(8) 0.2116(2) 0.40654(8) 0.0266(3) Uani d 1 . .
H H6 0.612378 0.082452 0.394429 0.032 Uiso calc 1 . .
C C12 0.84327(8) 0.7775(2) 0.68750(8) 0.0274(3) Uani d 1 . .
H H12 0.881670 0.885313 0.697783 0.033 Uiso calc 1 . .
C C11 0.85719(8) 0.6075(2) 0.73576(7) 0.0283(3) Uani d 1 . .
H H11 0.904654 0.600345 0.779703 0.034 Uiso calc 1 . .
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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3A N3 H3 . . 124.7 ?
C2 N3 H3 . . 124.7 ?
C2 N3 C3A . . 110.58(11) ?
C7A N1 C8 . . 126.52(11) ?
C2 N1 C8 . . 123.83(11) ?
C2 N1 C7A . . 109.60(10) ?
C9 C8 N1 . . 120.15(12) ?
C13 C8 N1 . . 118.93(12) ?
C13 C8 C9 . . 120.91(12) ?
N1 C7A C3A . . 106.37(12) ?
C7 C7A N1 . . 131.98(12) ?
C7 C7A C3A . . 121.64(12) ?
N3 C3A C7A . . 107.14(11) ?
C4 C3A N3 . . 131.89(12) ?
C4 C3A C7A . . 120.97(13) ?
O1 C2 N3 . . 127.84(12) ?
O1 C2 N1 . . 125.88(11) ?
N3 C2 N1 . . 106.28(11) ?
C8 C9 H9 . . 120.4 ?
C8 C9 C10 . . 119.16(14) ?
C10 C9 H9 . . 120.4 ?
C8 C13 H13 . . 120.3 ?
C8 C13 C12 . . 119.38(13) ?
C12 C13 H13 . . 120.3 ?
C7A C7 H7 . . 121.3 ?
C7A C7 C6 . . 117.46(12) ?
C6 C7 H7 . . 121.3 ?
C3A C4 H4 . . 121.3 ?
C3A C4 C5 . . 117.46(12) ?
C5 C4 H4 . . 121.3 ?
C4 C5 H5 . . 119.3 ?
C4 C5 C6 . . 121.45(13) ?
C6 C5 H5 . . 119.3 ?
C9 C10 H10 . . 119.9 ?
C11 C10 C9 . . 120.28(14) ?
C11 C10 H10 . . 119.9 ?
C7 C6 H6 . . 119.5 ?
C5 C6 C7 . . 121.00(14) ?
C5 C6 H6 . . 119.5 ?
C13 C12 H12 . . 120.0 ?
C11 C12 C13 . . 120.03(13) ?
C11 C12 H12 . . 120.0 ?
C10 C11 C12 . . 120.23(12) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.2282(16) ?
N3 H3 . 0.8800 ?
N3 C3A . 1.3824(18) ?
N3 C2 . 1.3660(16) ?
N1 C8 . 1.4266(15) ?
N1 C7A . 1.3988(17) ?
N1 C2 . 1.3864(17) ?
C8 C9 . 1.3868(19) ?
C8 C13 . 1.3867(19) ?
C7A C3A . 1.4004(17) ?
C7A C7 . 1.375(2) ?
C3A C4 . 1.3803(18) ?
C9 H9 . 0.9500 ?
C9 C10 . 1.3893(18) ?
C13 H13 . 0.9500 ?
C13 C12 . 1.3896(18) ?
C7 H7 . 0.9500 ?
C7 C6 . 1.3920(19) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.390(2) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.390(2) ?
C10 H10 . 0.9500 ?
C10 C11 . 1.384(2) ?
C6 H6 . 0.9500 ?
C12 H12 . 0.9500 ?
C12 C11 . 1.384(2) ?
C11 H11 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3 O1 5_676 0.88 1.91 2.7786(14) 177 yes
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
_geom_torsion_publ_flag
N3 C3A C4 C5 . . . . 178.80(13) ?
N1 C8 C9 C10 . . . . -177.25(12) ?
N1 C8 C13 C12 . . . . 177.74(12) ?
N1 C7A C3A N3 . . . . -0.29(13) ?
N1 C7A C3A C4 . . . . 179.34(11) ?
N1 C7A C7 C6 . . . . -178.35(12) ?
C8 N1 C7A C3A . . . . 178.81(11) ?
C8 N1 C7A C7 . . . . -1.8(2) ?
C8 N1 C2 O1 . . . . 0.7(2) ?
C8 N1 C2 N3 . . . . -179.32(11) ?
C8 C9 C10 C11 . . . . -0.6(2) ?
C8 C13 C12 C11 . . . . -0.3(2) ?
C7A N1 C8 C9 . . . . -54.27(17) ?
C7A N1 C8 C13 . . . . 126.85(14) ?
C7A N1 C2 O1 . . . . 178.38(12) ?
C7A N1 C2 N3 . . . . -1.62(14) ?
C7A C3A C4 C5 . . . . -0.72(19) ?
C7A C7 C6 C5 . . . . -0.96(19) ?
C3A N3 C2 O1 . . . . -178.55(13) ?
C3A N3 C2 N1 . . . . 1.45(14) ?
C3A C7A C7 C6 . . . . 0.98(19) ?
C3A C4 C5 C6 . . . . 0.7(2) ?
C2 N3 C3A C7A . . . . -0.73(14) ?
C2 N3 C3A C4 . . . . 179.69(13) ?
C2 N1 C8 C9 . . . . 123.03(14) ?
C2 N1 C8 C13 . . . . -55.86(17) ?
C2 N1 C7A C3A . . . . 1.19(14) ?
C2 N1 C7A C7 . . . . -179.40(13) ?
C9 C8 C13 C12 . . . . -1.1(2) ?
C9 C10 C11 C12 . . . . -0.8(2) ?
C13 C8 C9 C10 . . . . 1.62(19) ?
C13 C12 C11 C10 . . . . 1.3(2) ?
C7 C7A C3A N3 . . . . -179.77(11) ?
C7 C7A C3A C4 . . . . -0.14(19) ?
C4 C5 C6 C7 . . . . 0.1(2) ?
