#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/45/2204553.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_2204553
loop_
_publ_author_name
'Daqing Shi'
'Zhengyi Li'
'Chunling Shi'
'Xiangshan Wang'
'Yong Zhang'
_publ_section_title
;
 3-(4-Chlorophenyl)-3,4-dihydroquinazolin-2(1H)-one
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2011
_journal_page_last               o2013
_journal_paper_doi               10.1107/S1600536804025218
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C14 H11 Cl N2 O'
_chemical_formula_moiety         'C14 H11 Cl N2 O'
_chemical_formula_sum            'C14 H11 Cl N2 O'
_chemical_formula_weight         258.70
_chemical_melting_point          552.5(5)
_chemical_name_systematic
;
3-(4-Chlorophenyl)-3,4-dihydroquinazolin-2(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                 111.329(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.788(2)
_cell_length_b                   13.142(3)
_cell_length_c                   10.114(2)
_cell_measurement_reflns_used    5478
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1211.9(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2003)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13104
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.78
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.9146
_exptl_absorpt_correction_T_min  0.8205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.355
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.045P)²+0.4313P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                2596
_reflns_number_total             2767
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6418.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '552-553' was changed to '552.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '552-553' was changed to '552.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204553
_cod_database_fobs_code          2204553
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_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_type_symbol
Cl1 1.17552(4) 0.08482(3) 1.23922(4) 0.03801(13) Uani d . 1 Cl
O1 0.65179(10) 0.40940(7) 1.05253(10) 0.0294(2) Uani d . 1 O
N1 0.57442(13) 0.51126(9) 0.85885(13) 0.0316(3) Uani d . 1 N
N2 0.76210(12) 0.39581(9) 0.88803(11) 0.0269(2) Uani d . 1 N
C1 0.66197(13) 0.43694(10) 0.93965(14) 0.0254(3) Uani d . 1 C
C2 0.74234(17) 0.40419(11) 0.73756(14) 0.0344(3) Uani d . 1 C
H2A 0.6756 0.3497 0.6833 0.041 Uiso calc R 1 H
H2B 0.8381 0.3948 0.7267 0.041 Uiso calc R 1 H
C3 0.67993(14) 0.50578(10) 0.67866(14) 0.0287(3) Uani d . 1 C
C4 0.59493(14) 0.55671(11) 0.74218(14) 0.0288(3) Uani d . 1 C
C5 0.69748(15) 0.54795(11) 0.55997(15) 0.0332(3) Uani d . 1 C
H5 0.7539 0.5130 0.5152 0.040 Uiso calc R 1 H
C6 0.63332(16) 0.64073(12) 0.50611(16) 0.0375(3) Uani d . 1 C
H6 0.6457 0.6692 0.4249 0.045 Uiso calc R 1 H
C7 0.55076(17) 0.69171(12) 0.57205(16) 0.0383(3) Uani d . 1 C
H7 0.5073 0.7554 0.5359 0.046 Uiso calc R 1 H
C8 0.53153(15) 0.65020(11) 0.68998(15) 0.0347(3) Uani d . 1 C
H8 0.4754 0.6853 0.7349 0.042 Uiso calc R 1 H
C9 0.86292(13) 0.32077(10) 0.97114(13) 0.0247(3) Uani d . 1 C
C10 0.86808(14) 0.22494(10) 0.91564(14) 0.0284(3) Uani d . 1 C
H10 0.8039 0.2086 0.8221 0.034 Uiso calc R 1 H
C11 0.96687(15) 0.15283(10) 0.99654(15) 0.0303(3) Uani d . 1 C
H11 0.9715 0.0874 0.9585 0.036 Uiso calc R 1 H
C12 1.05842(14) 0.17722(10) 1.13298(14) 0.0273(3) Uani d . 1 C
C13 1.05681(15) 0.27301(11) 1.18835(15) 0.0338(3) Uani d . 1 C
H13 1.1219 0.2894 1.2815 0.041 Uiso calc R 1 H
C14 0.95910(15) 0.34496(11) 1.10649(15) 0.0335(3) Uani d . 1 C
H14 0.9579 0.4113 1.1433 0.040 Uiso calc R 1 H
H1 0.511(2) 0.5347(13) 0.8912(18) 0.039(4) Uiso d . 1 H
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C1 N1 C4 124.12(11) y
C1 N1 H1 114.5(12) ?
C4 N1 H1 120.9(12) ?
C1 N2 C9 118.77(11) y
C1 N2 C2 121.35(11) y
C9 N2 C2 117.61(10) y
O1 C1 N1 121.39(11) y
O1 C1 N2 122.87(12) y
N1 C1 N2 115.73(12) y
N2 C2 C3 111.11(11) y
N2 C2 H2A 109.4 ?
C3 C2 H2A 109.4 ?
N2 C2 H2B 109.4 ?
C3 C2 H2B 109.4 ?
H2A C2 H2B 108.0 ?
C5 C3 C4 119.29(13) ?
C5 C3 C2 122.59(12) ?
C4 C3 C2 118.04(12) ?
C8 C4 C3 120.53(13) ?
C8 C4 N1 121.04(12) no
C3 C4 N1 118.43(12) no
C3 C5 C6 120.60(13) ?
C3 C5 H5 119.7 ?
C6 C5 H5 119.7 ?
C5 C6 C7 119.54(14) ?
C5 C6 H6 120.2 ?
C7 C6 H6 120.2 ?
C8 C7 C6 120.48(14) ?
C8 C7 H7 119.8 ?
C6 C7 H7 119.8 ?
C7 C8 C4 119.55(13) ?
C7 C8 H8 120.2 ?
C4 C8 H8 120.2 ?
C14 C9 C10 119.73(12) ?
C14 C9 N2 119.80(12) no
C10 C9 N2 120.44(11) no
C9 C10 C11 120.09(12) ?
C9 C10 H10 120.0 ?
C11 C10 H10 120.0 ?
C12 C11 C10 119.32(12) ?
C12 C11 H11 120.3 ?
C10 C11 H11 120.3 ?
C13 C12 C11 121.18(12) ?
C13 C12 Cl1 119.11(11) ?
C11 C12 Cl1 119.69(11) ?
C12 C13 C14 119.17(13) ?
C12 C13 H13 120.4 ?
C14 C13 H13 120.4 ?
C13 C14 C9 120.45(13) ?
C13 C14 H14 119.8 ?
C9 C14 H14 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C12 1.7456(13) ?
O1 C1 1.2358(17) y
N1 C1 1.3589(17) y
N1 C4 1.4006(18) y
N1 H1 0.861(18) ?
N2 C1 1.3775(16) y
N2 C9 1.4317(16) y
N2 C2 1.4668(17) y
C2 C3 1.4986(19) y
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 C5 1.388(2) ?
C3 C4 1.3935(18) ?
C4 C8 1.391(2) ?
C5 C6 1.389(2) ?
C5 H5 0.9500 ?
C6 C7 1.392(2) ?
C6 H6 0.9500 ?
C7 C8 1.385(2) ?
C7 H7 0.9500 ?
C8 H8 0.9500 ?
C9 C14 1.3869(19) ?
C9 C10 1.3872(18) ?
C10 C11 1.3881(19) ?
C10 H10 0.9500 ?
C11 C12 1.3822(19) ?
C11 H11 0.9500 ?
C12 C13 1.380(2) ?
C13 C14 1.3850(19) ?
C13 H13 0.9500 ?
C14 H14 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
N1 H1 O1 3_667 0.861(18) 2.012(19) 2.8699(15) 174.5(16)
C7 H7 O1 2_656 0.95 2.51 3.4477(18) 169
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_publ_flag
C4 N1 C1 O1 169.77(12) no
C4 N1 C1 N2 -9.71(19) y
C9 N2 C1 O1 -2.58(19) no
C2 N2 C1 O1 159.91(13) no
C9 N2 C1 N1 176.89(11) y
C2 N2 C1 N1 -20.61(18) y
C1 N2 C2 C3 37.78(18) y
C9 N2 C2 C3 -159.53(12) y
N2 C2 C3 C5 156.71(13) y
N2 C2 C3 C4 -26.63(18) y
C5 C3 C4 C8 -1.8(2) ?
C2 C3 C4 C8 -178.57(13) ?
C5 C3 C4 N1 177.85(12) no
C2 C3 C4 N1 1.07(19) y
C1 N1 C4 C8 -160.96(13) y
C1 N1 C4 C3 19.4(2) y
C4 C3 C5 C6 1.1(2) no
C2 C3 C5 C6 177.72(14) ?
C3 C5 C6 C7 0.0(2) ?
C5 C6 C7 C8 -0.4(2) ?
C6 C7 C8 C4 -0.2(2) ?
C3 C4 C8 C7 1.4(2) ?
N1 C4 C8 C7 -178.26(13) no
C1 N2 C9 C14 -59.84(17) y
C2 N2 C9 C14 137.01(14) no
C1 N2 C9 C10 122.08(13) no
C2 N2 C9 C10 -41.07(17) y
C14 C9 C10 C11 1.5(2) ?
N2 C9 C10 C11 179.54(12) ?
C9 C10 C11 C12 0.7(2) ?
C10 C11 C12 C13 -2.2(2) ?
C10 C11 C12 Cl1 176.30(10) ?
C11 C12 C13 C14 1.5(2) ?
Cl1 C12 C13 C14 -177.02(11) ?
C12 C13 C14 C9 0.7(2) ?
C10 C9 C14 C13 -2.2(2) ?
N2 C9 C14 C13 179.72(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130285
