#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/12/2211206.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_2211206
loop_
_publ_author_name
'Nagarajan Vembu'
'Elinor C. Spencer'
'Jean Lee'
'John G. Kelly'
'Kevin B. Nolan'
'Marc Devocelle'
_publ_section_title
;
 5-Chloro-3-hydroxy-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one:
 supramolecular aggregation through a two-dimensional network of
 N---H···O and O---H···O
 interactions
;
_journal_coeditor_code           SJ2138
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5003
_journal_page_last               o5005
_journal_paper_doi               10.1107/S1600536806040852
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H11 Cl N2 O2'
_chemical_formula_moiety         'C10 H11 Cl N2 O2'
_chemical_formula_sum            'C10 H11 Cl N2 O2'
_chemical_formula_weight         226.66
_chemical_name_common            Chlorohydroxydimethyldihydroquinazolinone
_chemical_name_systematic
;
5-Chloro-3-hydroxy-2,2-dimethylquinazolin-4(1H)-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.7070(5)
_cell_length_b                   12.7121(7)
_cell_length_c                   16.4203(8)
_cell_measurement_reflns_used    2345
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.253
_cell_measurement_theta_min      2.479
_cell_volume                     2026.21(18)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'MERCURY (Macrae et al.,  2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 6K CCD area-detector'
_diffrn_measurement_method       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  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12430
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1998)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         1996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0376
_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)+(0.0571P)²+0.6859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                1507
_reflns_number_total             1996
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2138.cif
_cod_data_source_block           I
_cod_database_code               2211206
_cod_database_fobs_code          2211206
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
C C1 0.1625(2) 0.01410(16) 0.30349(13) 0.0232(5) Uani d 1
C C2 0.0732(2) 0.04246(18) 0.24247(14) 0.0272(5) Uani d 1
H H2 0.061(2) -0.0020(19) 0.1994(14) 0.030(6) Uiso d 1
C C3 0.0072(2) 0.13934(17) 0.24633(14) 0.0265(5) Uani d 1
H H3 -0.054(2) 0.1577(18) 0.2025(14) 0.028(6) Uiso d 1
C C4 0.0253(2) 0.20484(17) 0.31133(13) 0.0259(5) Uani d 1
H H4 -0.022(2) 0.2718(19) 0.3145(14) 0.032(6) Uiso d 1
C C5 0.11145(19) 0.17453(16) 0.37553(12) 0.0231(4) Uani d 1
C C6 0.18594(19) 0.07904(15) 0.37162(12) 0.0210(4) Uani d 1
C C7 0.2901(2) 0.05918(15) 0.43529(12) 0.0219(4) Uani d 1
C C8 0.2240(2) 0.28916(18) 0.57100(15) 0.0288(5) Uani d 1
H H8A 0.146(2) 0.3452(17) 0.5774(14) 0.030(6) Uiso d 1
H H8B 0.244(2) 0.2654(18) 0.6266(16) 0.030(6) Uiso d 1
H H8C 0.303(3) 0.320(2) 0.5486(15) 0.039(7) Uiso d 1
C C9 0.1737(2) 0.19813(16) 0.51952(12) 0.0245(5) Uani d 1
C C10 0.0626(2) 0.13579(19) 0.56367(15) 0.0313(5) Uani d 1
H H10C -0.015(3) 0.183(2) 0.5808(16) 0.047(7) Uiso d 1
H H10B 0.102(3) 0.101(2) 0.6148(18) 0.048(8) Uiso d 1
H H10A 0.022(3) 0.081(2) 0.5298(17) 0.050(8) Uiso d 1
H H2O 0.426(3) 0.057(2) 0.5458(17) 0.048(8) Uiso d 1
H H2N 0.102(3) 0.301(2) 0.4410(16) 0.047(8) Uiso d 1
Cl Cl1 0.24305(5) -0.10747(4) 0.29303(3) 0.02900(19) Uani d 1
N N1 0.28885(18) 0.12826(14) 0.49761(11) 0.0260(4) Uani d 1
N N2 0.12798(19) 0.23850(15) 0.44190(11) 0.0275(4) Uani d 1
O O1 0.38023(14) -0.01006(11) 0.43358(9) 0.0277(4) Uani d 1
O O2 0.37357(16) 0.10485(13) 0.56416(9) 0.0312(4) Uani 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'
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 C1 C6 121.83(19)
C2 C1 Cl1 116.40(16)
C6 C1 Cl1 121.76(16)
C1 C2 C3 119.4(2)
C1 C2 H2 119.0(15)
C3 C2 H2 121.6(15)
C4 C3 C2 121.1(2)
C4 C3 H3 121.1(14)
C2 C3 H3 117.8(14)
C3 C4 C5 119.9(2)
C3 C4 H4 121.0(14)
C5 C4 H4 119.1(14)
N2 C5 C4 120.40(19)
N2 C5 C6 119.08(18)
C4 C5 C6 120.49(19)
C1 C6 C5 117.16(18)
C1 C6 C7 124.94(18)
C5 C6 C7 117.69(18)
O1 C7 N1 119.01(18)
O1 C7 C6 126.01(19)
N1 C7 C6 114.85(17)
C9 C8 H8A 110.0(13)
C9 C8 H8B 110.4(14)
H8A C8 H8B 105.0(19)
C9 C8 H8C 111.2(16)
H8A C8 H8C 111(2)
H8B C8 H8C 109(2)
N2 C9 N1 103.41(16)
N2 C9 C8 108.69(17)
N1 C9 C8 110.62(17)
N2 C9 C10 112.83(18)
N1 C9 C10 109.90(17)
C8 C9 C10 111.14(18)
C9 C10 H10C 110.6(15)
C9 C10 H10B 110.7(16)
H10C C10 H10B 108(2)
C9 C10 H10A 112.7(16)
H10C C10 H10A 107(2)
H10B C10 H10A 108(2)
C7 N1 O2 116.67(16)
C7 N1 C9 125.78(17)
O2 N1 C9 112.57(16)
C5 N2 C9 121.84(17)
C5 N2 H2N 121.1(19)
C9 N2 H2N 116.5(19)
N1 O2 H2O 103.1(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.373(3)
C1 C6 1.409(3)
C1 Cl1 1.740(2)
C2 C3 1.390(3)
C2 H2 0.91(2)
C3 C4 1.365(3)
C3 H3 0.96(2)
C4 C5 1.399(3)
C4 H4 0.97(2)
C5 N2 1.369(3)
C5 C6 1.414(3)
C6 C7 1.476(3)
C7 O1 1.242(2)
C7 N1 1.349(3)
C8 C9 1.514(3)
C8 H8A 1.05(2)
C8 H8B 0.98(3)
C8 H8C 0.93(3)
C9 N2 1.444(3)
C9 N1 1.473(3)
C9 C10 1.522(3)
C10 H10C 1.00(3)
C10 H10B 1.02(3)
C10 H10A 0.98(3)
N1 O2 1.400(2)
N2 H2N 0.83(3)
O2 H2O 0.85(3)
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
N2 H2N O2 4_456 0.83(3) 2.52(3) 3.174(2) 136(2) y
N2 H2N O1 8_665 0.83(3) 2.41(3) 3.200(2) 158(2) y
O2 H2O O1 . 0.85(3) 2.08(3) 2.595(2) 119(2) y
O2 H2O O1 5_656 0.85(3) 2.00(3) 2.677(2) 136(2) y
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
C6 C1 C2 C3 2.1(3) ?
Cl1 C1 C2 C3 -178.94(16) ?
C1 C2 C3 C4 -2.7(3) ?
C2 C3 C4 C5 -0.1(3) ?
C3 C4 C5 N2 -178.50(19) ?
C3 C4 C5 C6 3.5(3) ?
C2 C1 C6 C5 1.1(3) ?
Cl1 C1 C6 C5 -177.76(14) ?
C2 C1 C6 C7 -173.57(19) ?
Cl1 C1 C6 C7 7.6(3) ?
N2 C5 C6 C1 178.05(18) ?
C4 C5 C6 C1 -3.9(3) ?
N2 C5 C6 C7 -6.9(3) y
C4 C5 C6 C7 171.16(18) ?
C1 C6 C7 O1 8.1(3) ?
C5 C6 C7 O1 -166.55(19) ?
C1 C6 C7 N1 -176.11(19) y
C5 C6 C7 N1 9.2(3) ?
O1 C7 N1 O2 -11.8(3) y
C6 C7 N1 O2 172.09(16) y
O1 C7 N1 C9 -164.85(19) ?
C6 C7 N1 C9 19.0(3) y
N2 C9 N1 C7 -43.6(3) y
C8 C9 N1 C7 -159.8(2) y
C10 C9 N1 C7 77.1(3) y
N2 C9 N1 O2 162.41(16) y
C8 C9 N1 O2 46.2(2) ?
C10 C9 N1 O2 -76.9(2) ?
C4 C5 N2 C9 157.99(19) ?
C6 C5 N2 C9 -24.0(3) y
N1 C9 N2 C5 44.8(2) y
C8 C9 N2 C5 162.40(18) y
C10 C9 N2 C5 -73.9(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126087
