#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/33/8103319.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_8103319
loop_
_publ_author_name
'Lan-Qin Chai'
'Yu-Li Zhang'
'Kai Cui'
'Zai-Rui Wang'
'Li-Wen Zhang'
'Yong-Ze Zhang'
_publ_section_title
;
 Crystal structure of
 2-(3,5-dichloro-2-hydroxyphenyl)-4-methyl-1,2-dihydroquinazoline 3-oxide,
 C15H12Cl2N2O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              153
_journal_volume                  227
_journal_year                    2012
_chemical_formula_sum            'C15 H12 Cl2 N2 O2'
_chemical_formula_weight         323.17
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.8770(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7831(11)
_cell_length_b                   14.6259(13)
_cell_length_c                   9.7936(7)
_cell_measurement_reflns_used    2723
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.202
_cell_measurement_theta_min      2.535
_cell_volume                     1377.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6794
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_T_max  0.8943
_exptl_absorpt_correction_T_min  0.8250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0349
_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)+(0.0494P)²+0.4631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0985
_reflns_number_gt                1829
_reflns_number_total             2417
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3655.cff
_cod_data_source_block           110809g
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               8103319
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl -0.11378(7) 0.62166(4) 0.29764(8) 0.0457(2) Uani 1 1 d .
Cl2 Cl 0.20063(7) 0.70120(4) 0.01584(8) 0.0457(2) Uani 1 1 d .
N1 N 0.27295(19) 0.34853(11) 0.3841(2) 0.0262(4) Uani 1 1 d .
N2 N 0.2762(2) 0.34999(12) 0.1414(2) 0.0311(4) Uani 1 1 d .
H2 H 0.2416 0.3220 0.0548 0.037 Uiso 1 1 calc R
O1 O 0.19550(16) 0.31942(11) 0.44914(18) 0.0347(4) Uani 1 1 d .
O2 O -0.00159(17) 0.44001(11) 0.32426(19) 0.0383(4) Uani 1 1 d .
H2A H 0.0524 0.3973 0.3626 0.057 Uiso 1 1 calc R
C1 C 0.4776(3) 0.35131(17) 0.6276(3) 0.0377(6) Uani 1 1 d .
H1A H 0.4098 0.3382 0.6631 0.057 Uiso 1 1 calc R
H1B H 0.5263 0.4065 0.6748 0.057 Uiso 1 1 calc R
H1C H 0.5426 0.3016 0.6541 0.057 Uiso 1 1 calc R
C2 C 0.4066(2) 0.36305(14) 0.4582(3) 0.0269(5) Uani 1 1 d .
C3 C 0.4810(2) 0.38842(14) 0.3715(3) 0.0279(5) Uani 1 1 d .
C4 C 0.4151(2) 0.37678(14) 0.2119(3) 0.0298(5) Uani 1 1 d .
C5 C 0.4898(3) 0.39063(17) 0.1294(3) 0.0409(6) Uani 1 1 d .
H5 H 0.4470 0.3821 0.0239 0.049 Uiso 1 1 calc R
C6 C 0.6278(3) 0.41710(19) 0.2043(3) 0.0484(7) Uani 1 1 d .
H6 H 0.6774 0.4258 0.1485 0.058 Uiso 1 1 calc R
C7 C 0.6932(3) 0.43085(17) 0.3612(3) 0.0445(7) Uani 1 1 d .
H7 H 0.7853 0.4501 0.4101 0.053 Uiso 1 1 calc R
C8 C 0.6207(3) 0.41577(15) 0.4438(3) 0.0355(6) Uani 1 1 d .
H8 H 0.6650 0.4238 0.5494 0.043 Uiso 1 1 calc R
C9 C 0.1930(2) 0.37005(14) 0.2160(2) 0.0261(5) Uani 1 1 d .
H9 H 0.1108 0.3305 0.1724 0.031 Uiso 1 1 calc R
C10 C 0.1434(2) 0.46974(14) 0.1985(2) 0.0246(5) Uani 1 1 d .
C11 C 0.0497(2) 0.49677(15) 0.2538(2) 0.0271(5) Uani 1 1 d .
C12 C 0.0043(2) 0.58784(16) 0.2325(3) 0.0298(5) Uani 1 1 d .
C13 C 0.0511(2) 0.65117(15) 0.1620(2) 0.0310(5) Uani 1 1 d .
H13 H 0.0219 0.7117 0.1514 0.037 Uiso 1 1 calc R
C14 C 0.1425(2) 0.62214(15) 0.1075(2) 0.0298(5) Uani 1 1 d .
C15 C 0.1873(2) 0.53279(14) 0.1237(2) 0.0269(5) Uani 1 1 d .
H15 H 0.2473 0.5146 0.0843 0.032 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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
C2 N1 O1 124.11(18)
C2 N1 C9 121.10(17)
O1 N1 C9 114.68(17)
C4 N2 C9 118.31(18)
C4 N2 H2 120.8
C9 N2 H2 120.8
C11 O2 H2A 109.5
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C3 118.6(2)
N1 C2 C1 118.9(2)
C3 C2 C1 122.5(2)
C8 C3 C4 119.0(2)
C8 C3 C2 121.8(2)
C4 C3 C2 118.9(2)
C5 C4 N2 121.9(2)
C5 C4 C3 119.6(2)
N2 C4 C3 118.5(2)
C6 C5 C4 119.9(2)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C7 121.0(2)
C5 C6 H6 119.5
C7 C6 H6 119.5
C8 C7 C6 119.3(2)
C8 C7 H7 120.3
C6 C7 H7 120.3
C7 C8 C3 121.1(2)
C7 C8 H8 119.5
C3 C8 H8 119.5
N2 C9 N1 109.68(17)
N2 C9 C10 114.07(17)
N1 C9 C10 108.58(16)
N2 C9 H9 108.1
N1 C9 H9 108.1
C10 C9 H9 108.1
C15 C10 C11 119.61(19)
C15 C10 C9 120.33(19)
C11 C10 C9 120.02(18)
O2 C11 C12 117.74(19)
O2 C11 C10 123.93(19)
C12 C11 C10 118.3(2)
C13 C12 C11 122.0(2)
C13 C12 Cl1 119.20(17)
C11 C12 Cl1 118.77(17)
C12 C13 C14 118.2(2)
C12 C13 H13 120.9
C14 C13 H13 120.9
C15 C14 C13 121.4(2)
C15 C14 Cl2 119.98(18)
C13 C14 Cl2 118.67(17)
C14 C15 C10 120.4(2)
C14 C15 H15 119.8
C10 C15 H15 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C12 1.734(2)
Cl2 C14 1.745(2)
N1 C2 1.305(3)
N1 O1 1.329(2)
N1 C9 1.506(3)
N2 C4 1.392(3)
N2 C9 1.420(3)
N2 H2 0.8600
O2 C11 1.347(3)
O2 H2A 0.8200
C1 C2 1.489(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.457(3)
C3 C8 1.402(3)
C3 C4 1.404(3)
C4 C5 1.390(3)
C5 C6 1.384(4)
C5 H5 0.9300
C6 C7 1.385(4)
C6 H6 0.9300
C7 C8 1.374(3)
C7 H7 0.9300
C8 H8 0.9300
C9 C10 1.536(3)
C9 H9 0.9800
C10 C15 1.388(3)
C10 C11 1.402(3)
C11 C12 1.402(3)
C12 C13 1.380(3)
C13 C14 1.383(3)
C13 H13 0.9300
C14 C15 1.377(3)
C15 H15 0.9300
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
O1 N1 C2 C3 175.49(18)
C9 N1 C2 C3 -8.5(3)
O1 N1 C2 C1 -3.3(3)
C9 N1 C2 C1 172.69(18)
N1 C2 C3 C8 172.2(2)
C1 C2 C3 C8 -9.1(3)
N1 C2 C3 C4 -14.0(3)
C1 C2 C3 C4 164.8(2)
C9 N2 C4 C5 -156.5(2)
C9 N2 C4 C3 24.6(3)
C8 C3 C4 C5 1.3(3)
C2 C3 C4 C5 -172.7(2)
C8 C3 C4 N2 -179.72(19)
C2 C3 C4 N2 6.3(3)
N2 C4 C5 C6 -179.9(2)
C3 C4 C5 C6 -1.0(3)
C4 C5 C6 C7 -0.5(4)
C5 C6 C7 C8 1.6(4)
C6 C7 C8 C3 -1.2(4)
C4 C3 C8 C7 -0.2(3)
C2 C3 C8 C7 173.6(2)
C4 N2 C9 N1 -43.7(2)
C4 N2 C9 C10 78.3(2)
C2 N1 C9 N2 36.4(2)
O1 N1 C9 N2 -147.29(17)
C2 N1 C9 C10 -88.9(2)
O1 N1 C9 C10 87.5(2)
N2 C9 C10 C15 -4.0(3)
N1 C9 C10 C15 118.6(2)
N2 C9 C10 C11 173.87(19)
N1 C9 C10 C11 -63.5(2)
C15 C10 C11 O2 178.22(19)
C9 C10 C11 O2 0.3(3)
C15 C10 C11 C12 -0.6(3)
C9 C10 C11 C12 -178.53(19)
O2 C11 C12 C13 179.8(2)
C10 C11 C12 C13 -1.3(3)
O2 C11 C12 Cl1 0.1(3)
C10 C11 C12 Cl1 178.96(17)
C11 C12 C13 C14 1.9(3)
Cl1 C12 C13 C14 -178.37(17)
C12 C13 C14 C15 -0.6(3)
C12 C13 C14 Cl2 179.18(17)
C13 C14 C15 C10 -1.3(3)
Cl2 C14 C15 C10 178.98(17)
C11 C10 C15 C14 1.9(3)
C9 C10 C15 C14 179.8(2)
