#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/59/2225955.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_2225955
loop_
_publ_author_name
'Zhang, Mei-Mei'
'Yang, Ke'
'Wang, Xiang-Shan'
_publ_section_title
;
 2-(4-Bromophenyl)-2-methyl-2,3-dihydroquinazolin-4(1H)-one
;
_journal_coeditor_code           PV2270
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1069
_journal_paper_doi               10.1107/S1600536810012584
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H13 Br N2 O'
_chemical_formula_moiety         'C15 H13 Br N2 O'
_chemical_formula_sum            'C15 H13 Br N2 O'
_chemical_formula_weight         317.18
_chemical_melting_point_gt       494
_chemical_melting_point_lt       496
_chemical_name_systematic
;
2-(4-Bromophenyl)-2-methyl-2,3-dihydroquinazolin-4(1H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.7190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2106(3)
_cell_length_b                   9.0507(2)
_cell_length_c                   12.4046(3)
_cell_measurement_reflns_used    7144
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.81
_cell_volume                     1342.31(6)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16905
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    3.055
_exptl_absorpt_correction_T_max  0.8013
_exptl_absorpt_correction_T_min  0.3434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.885
_refine_diff_density_min         -0.857
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2369
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0402P)²+1.4299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0873
_reflns_number_gt                2068
_reflns_number_total             2369
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2270.cif
_cod_data_source_block           I
_cod_original_cell_volume        1342.31(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225955
_cod_database_fobs_code          2225955
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.39200(3) 0.15530(4) 0.53610(3) 0.06231(16) Uani d . 1 . .
O O1 0.12331(16) 0.5903(2) -0.02983(14) 0.0438(5) Uani d . 1 . .
N N2 0.14117(19) 0.7611(2) 0.27005(18) 0.0356(5) Uani d D 1 . .
C C2 0.1400(2) 0.6296(3) 0.0687(2) 0.0331(6) Uani d . 1 . .
C C10 0.1575(2) 0.4972(3) 0.3192(2) 0.0305(5) Uani d . 1 . .
N N1 0.07053(18) 0.5872(3) 0.13329(17) 0.0341(5) Uani d D 1 . .
C C15 0.1462(2) 0.4648(3) 0.4258(2) 0.0423(6) Uani d . 1 . .
H H15A 0.0918 0.5136 0.4550 0.051 Uiso calc R 1 . .
C C8 0.2278(2) 0.7955(3) 0.2193(2) 0.0339(6) Uani d . 1 . .
C C7 0.3078(2) 0.9022(3) 0.2615(2) 0.0430(7) Uani d . 1 . .
H H7A 0.3047 0.9501 0.3271 0.052 Uiso calc R 1 . .
C C11 0.2387(2) 0.4209(3) 0.2788(2) 0.0371(6) Uani d . 1 . .
H H11A 0.2471 0.4391 0.2071 0.045 Uiso calc R 1 . .
C C3 0.2318(2) 0.7284(3) 0.1177(2) 0.0342(6) Uani d . 1 . .
C C9 -0.0294(2) 0.6307(3) 0.2795(2) 0.0418(6) Uani d . 1 . .
H H9A -0.0752 0.6953 0.2278 0.050 Uiso calc R 1 . .
H H9B -0.0224 0.6699 0.3525 0.050 Uiso calc R 1 . .
H H9C -0.0633 0.5346 0.2760 0.050 Uiso calc R 1 . .
C C1 0.0863(2) 0.6182(3) 0.2514(2) 0.0312(5) Uani d . 1 . .
C C13 0.2944(2) 0.2903(3) 0.4473(2) 0.0396(6) Uani d . 1 . .
C C14 0.2138(3) 0.3620(3) 0.4894(2) 0.0462(7) Uani d . 1 . .
H H14A 0.2046 0.3415 0.5605 0.055 Uiso calc R 1 . .
C C4 0.3171(2) 0.7652(3) 0.0637(2) 0.0417(6) Uani d . 1 . .
H H4A 0.3202 0.7199 -0.0030 0.050 Uiso calc R 1 . .
C C5 0.3972(2) 0.8676(4) 0.1070(3) 0.0494(7) Uani d . 1 . .
H H5A 0.4546 0.8906 0.0707 0.059 Uiso calc R 1 . .
C C12 0.3077(2) 0.3185(3) 0.3416(2) 0.0416(6) Uani d . 1 . .
H H12A 0.3623 0.2693 0.3129 0.050 Uiso calc R 1 . .
C C6 0.3913(3) 0.9364(3) 0.2060(3) 0.0500(7) Uani d . 1 . .
H H6A 0.4447 1.0067 0.2352 0.060 Uiso calc R 1 . .
H H2 0.146(2) 0.794(3) 0.3350(12) 0.042(8) Uiso d D 1 . .
H H1 0.0147(16) 0.535(3) 0.103(2) 0.035(7) Uiso d D 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'
Br Br -0.2901 2.4595 '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
C8 N2 C1 . . 120.2(2) ?
C8 N2 H2 . . 116(2) ?
C1 N2 H2 . . 114(2) ?
O1 C2 N1 . . 120.5(2) ?
O1 C2 C3 . . 122.6(2) ?
N1 C2 C3 . . 116.8(2) ?
C11 C10 C15 . . 117.2(2) ?
C11 C10 C1 . . 121.6(2) ?
C15 C10 C1 . . 121.1(2) ?
C2 N1 C1 . . 125.0(2) ?
C2 N1 H1 . . 116.3(19) ?
C1 N1 H1 . . 118.5(19) ?
C14 C15 C10 . . 121.6(3) ?
C14 C15 H15A . . 119.2 ?
C10 C15 H15A . . 119.2 ?
N2 C8 C7 . . 122.1(2) ?
N2 C8 C3 . . 118.9(2) ?
C7 C8 C3 . . 118.9(2) ?
C6 C7 C8 . . 120.1(3) ?
C6 C7 H7A . . 120.0 ?
C8 C7 H7A . . 120.0 ?
C12 C11 C10 . . 122.0(2) ?
C12 C11 H11A . . 119.0 ?
C10 C11 H11A . . 119.0 ?
C4 C3 C8 . . 119.6(2) ?
C4 C3 C2 . . 122.1(2) ?
C8 C3 C2 . . 118.1(2) ?
C1 C9 H9A . . 109.5 ?
C1 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C1 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N2 C1 N1 . . 107.0(2) ?
N2 C1 C9 . . 108.4(2) ?
N1 C1 C9 . . 107.6(2) ?
N2 C1 C10 . . 110.9(2) ?
N1 C1 C10 . . 110.8(2) ?
C9 C1 C10 . . 112.0(2) ?
C14 C13 C12 . . 120.6(3) ?
C14 C13 Br1 . . 120.0(2) ?
C12 C13 Br1 . . 119.4(2) ?
C13 C14 C15 . . 119.6(3) ?
C13 C14 H14A . . 120.2 ?
C15 C14 H14A . . 120.2 ?
C5 C4 C3 . . 121.1(3) ?
C5 C4 H4A . . 119.5 ?
C3 C4 H4A . . 119.5 ?
C4 C5 C6 . . 119.1(3) ?
C4 C5 H5A . . 120.4 ?
C6 C5 H5A . . 120.4 ?
C13 C12 C11 . . 119.0(3) ?
C13 C12 H12A . . 120.5 ?
C11 C12 H12A . . 120.5 ?
C7 C6 C5 . . 121.1(3) ?
C7 C6 H6A . . 119.4 ?
C5 C6 H6A . . 119.4 ?
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
Br1 C13 . 1.896(3) ?
O1 C2 . 1.249(3) ?
N2 C8 . 1.372(3) ?
N2 C1 . 1.453(3) ?
N2 H2 . 0.851(10) ?
C2 N1 . 1.336(3) ?
C2 C3 . 1.466(4) ?
C10 C11 . 1.384(4) ?
C10 C15 . 1.388(4) ?
C10 C1 . 1.538(3) ?
N1 C1 . 1.466(3) ?
N1 H1 . 0.854(10) ?
C15 C14 . 1.381(4) ?
C15 H15A . 0.9300 ?
C8 C7 . 1.397(4) ?
C8 C3 . 1.409(4) ?
C7 C6 . 1.376(4) ?
C7 H7A . 0.9300 ?
C11 C12 . 1.382(4) ?
C11 H11A . 0.9300 ?
C3 C4 . 1.389(4) ?
C9 C1 . 1.526(4) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C13 C14 . 1.368(4) ?
C13 C12 . 1.378(4) ?
C14 H14A . 0.9300 ?
C4 C5 . 1.375(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.391(4) ?
C5 H5A . 0.9300 ?
C12 H12A . 0.9300 ?
C6 H6A . 0.9300 ?
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
N1 H1 O1 3_565 0.854(10) 2.078(11) 2.932(3) 179(3)
N2 H2 O1 4_576 0.851(10) 2.041(13) 2.870(3) 164(3)
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
O1 C2 N1 C1 . . . . 175.6(2) ?
C3 C2 N1 C1 . . . . -7.2(4) ?
C11 C10 C15 C14 . . . . 0.6(4) ?
C1 C10 C15 C14 . . . . -176.5(3) ?
C1 N2 C8 C7 . . . . -156.5(2) ?
C1 N2 C8 C3 . . . . 27.8(4) ?
N2 C8 C7 C6 . . . . -178.0(3) ?
C3 C8 C7 C6 . . . . -2.4(4) ?
C15 C10 C11 C12 . . . . -1.2(4) ?
C1 C10 C11 C12 . . . . 175.9(2) ?
N2 C8 C3 C4 . . . . 178.1(2) ?
C7 C8 C3 C4 . . . . 2.4(4) ?
N2 C8 C3 C2 . . . . 2.7(4) ?
C7 C8 C3 C2 . . . . -173.1(2) ?
O1 C2 C3 C4 . . . . -11.0(4) ?
N1 C2 C3 C4 . . . . 171.9(2) ?
O1 C2 C3 C8 . . . . 164.4(2) ?
N1 C2 C3 C8 . . . . -12.8(3) ?
C8 N2 C1 N1 . . . . -43.0(3) ?
C8 N2 C1 C9 . . . . -158.8(2) ?
C8 N2 C1 C10 . . . . 77.9(3) ?
C2 N1 C1 N2 . . . . 33.1(3) ?
C2 N1 C1 C9 . . . . 149.4(2) ?
C2 N1 C1 C10 . . . . -87.8(3) ?
C11 C10 C1 N2 . . . . -88.1(3) ?
C15 C10 C1 N2 . . . . 88.9(3) ?
C11 C10 C1 N1 . . . . 30.5(3) ?
C15 C10 C1 N1 . . . . -152.5(2) ?
C11 C10 C1 C9 . . . . 150.7(2) ?
C15 C10 C1 C9 . . . . -32.4(3) ?
C12 C13 C14 C15 . . . . -0.8(5) ?
Br1 C13 C14 C15 . . . . 177.2(2) ?
C10 C15 C14 C13 . . . . 0.4(5) ?
C8 C3 C4 C5 . . . . -0.8(4) ?
C2 C3 C4 C5 . . . . 174.5(3) ?
C3 C4 C5 C6 . . . . -0.8(4) ?
C14 C13 C12 C11 . . . . 0.3(4) ?
Br1 C13 C12 C11 . . . . -177.8(2) ?
C10 C11 C12 C13 . . . . 0.7(4) ?
C8 C7 C6 C5 . . . . 0.8(5) ?
C4 C5 C6 C7 . . . . 0.8(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26249835
