#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/11/2221185.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_2221185
loop_
_publ_author_name
'Wang, Zhi-Gang'
'Wang, Rong'
'Zhang, Yi'
'Zhi, Feng'
'Yang, Yi-Lin'
_publ_section_title
2-[6,8-Dibromo-3-(4-hydroxycyclohexyl)-1,2,3,4-tetrahydroquinazolin-2-yl]-6-methoxyphenol
_journal_coeditor_code           SJ2575
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o550
_journal_paper_doi               10.1107/S1600536809005182
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H24 Br2 N2 O3'
_chemical_formula_moiety         'C21 H24 Br2 N2 O3'
_chemical_formula_sum            'C21 H24 Br2 N2 O3'
_chemical_formula_weight         512.24
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.870(3)
_cell_angle_beta                 78.226(3)
_cell_angle_gamma                67.031(2)
_cell_formula_units_Z            2
_cell_length_a                   8.695(2)
_cell_length_b                   11.124(3)
_cell_length_c                   12.090(2)
_cell_measurement_reflns_used    2079
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.6
_cell_measurement_theta_min      2.3
_cell_volume                     1028.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'ω 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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8514
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         1.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.967
_exptl_absorpt_correction_T_max  0.3824
_exptl_absorpt_correction_T_min  0.3824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.413
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0423P)²+0.0168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                3035
_reflns_number_total             4305
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj2575.cif
_cod_data_source_block           I
_cod_database_code               2221185
_cod_database_fobs_code          2221185
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 1.17738(5) 0.24247(4) 0.32321(4) 0.04726(14) Uani d . 1 . .
Br Br2 1.28346(5) 0.54977(4) 0.58131(3) 0.04402(14) Uani d . 1 . .
O O1 0.2331(3) 0.9422(3) 0.3052(2) 0.0418(7) Uani d . 1 . .
H H1 0.1581 0.9883 0.2635 0.063 Uiso calc R 1 . .
O O2 0.9413(3) 0.8807(3) -0.1082(2) 0.0430(7) Uani d . 1 . .
H H2 0.8961 0.8692 -0.0416 0.065 Uiso calc R 1 . .
O O3 1.1435(4) 0.9116(3) -0.2940(2) 0.0510(7) Uani d . 1 . .
N N1 1.0518(4) 0.5182(3) 0.1542(2) 0.0305(7) Uani d . 1 . .
H H1A 1.0527 0.4432 0.1469 0.037 Uiso calc R 1 . .
N N2 0.9133(3) 0.7617(3) 0.1103(2) 0.0249(6) Uani d . 1 . .
C C1 1.1053(4) 0.6460(3) 0.2638(3) 0.0265(8) Uani d . 1 . .
C C2 1.1080(4) 0.5243(3) 0.2507(3) 0.0263(7) Uani d . 1 . .
C C3 1.1674(4) 0.4110(3) 0.3381(3) 0.0287(8) Uani d . 1 . .
C C4 1.2199(4) 0.4172(3) 0.4357(3) 0.0317(8) Uani d . 1 . .
H H4 1.2586 0.3405 0.4931 0.038 Uiso calc R 1 . .
C C5 1.2143(4) 0.5386(4) 0.4468(3) 0.0302(8) Uani d . 1 . .
C C6 1.1591(4) 0.6523(3) 0.3620(3) 0.0306(8) Uani d . 1 . .
H H6 1.1576 0.7334 0.3702 0.037 Uiso calc R 1 . .
C C7 1.0414(4) 0.7698(3) 0.1692(3) 0.0259(7) Uani d . 1 . .
H H7A 0.9929 0.8481 0.2027 0.031 Uiso calc R 1 . .
H H7B 1.1349 0.7799 0.1128 0.031 Uiso calc R 1 . .
C C8 0.7481(4) 0.7705(3) 0.1797(3) 0.0269(8) Uani d . 1 . .
H H8 0.7560 0.6812 0.2263 0.032 Uiso calc R 1 . .
C C9 0.6954(4) 0.8659(4) 0.2601(3) 0.0377(9) Uani d . 1 . .
H H9A 0.6977 0.9525 0.2156 0.045 Uiso calc R 1 . .
H H9B 0.7751 0.8324 0.3168 0.045 Uiso calc R 1 . .
C C10 0.5210(5) 0.8823(4) 0.3222(3) 0.0410(10) Uani d . 1 . .
H H10A 0.5213 0.7973 0.3722 0.049 Uiso calc R 1 . .
H H10B 0.4908 0.9464 0.3705 0.049 Uiso calc R 1 . .
C C11 0.3920(4) 0.9293(3) 0.2392(3) 0.0322(8) Uani d . 1 . .
H H11 0.3880 1.0175 0.1918 0.039 Uiso calc R 1 . .
C C12 0.4406(4) 0.8330(4) 0.1607(3) 0.0414(10) Uani d . 1 . .
H H12A 0.3600 0.8662 0.1045 0.050 Uiso calc R 1 . .
H H12B 0.4380 0.7468 0.2062 0.050 Uiso calc R 1 . .
C C13 0.6155(4) 0.8160(4) 0.0976(3) 0.0378(9) Uani d . 1 . .
H H13A 0.6452 0.7509 0.0504 0.045 Uiso calc R 1 . .
H H13B 0.6143 0.9006 0.0463 0.045 Uiso calc R 1 . .
C C14 0.9912(4) 0.6381(3) 0.0655(3) 0.0255(7) Uani d . 1 . .
H H14 0.9030 0.6289 0.0329 0.031 Uiso calc R 1 . .
C C15 1.1251(4) 0.6565(4) -0.0355(3) 0.0296(8) Uani d . 1 . .
C C16 1.0875(4) 0.7752(4) -0.1185(3) 0.0298(8) Uani d . 1 . .
C C17 1.1986(5) 0.7917(4) -0.2178(3) 0.0367(9) Uani d . 1 . .
C C18 1.3514(5) 0.6900(5) -0.2301(3) 0.0454(11) Uani d . 1 . .
H H18 1.4274 0.7007 -0.2951 0.055 Uiso calc R 1 . .
C C19 1.3921(5) 0.5718(4) -0.1457(4) 0.0476(11) Uani d . 1 . .
H H19 1.4954 0.5038 -0.1541 0.057 Uiso calc R 1 . .
C C20 1.2793(4) 0.5554(4) -0.0496(3) 0.0368(9) Uani d . 1 . .
H H20 1.3068 0.4759 0.0063 0.044 Uiso calc R 1 . .
C C21 1.2282(7) 0.9219(5) -0.4076(3) 0.0797(17) Uani d . 1 . .
H H21A 1.3418 0.9132 -0.4048 0.120 Uiso calc R 1 . .
H H21B 1.1715 1.0074 -0.4549 0.120 Uiso calc R 1 . .
H H21C 1.2288 0.8521 -0.4400 0.120 Uiso calc R 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
C11 O1 H1 . . 109.5 ?
C16 O2 H2 . . 109.5 ?
C17 O3 C21 . . 117.3(3) ?
C2 N1 C14 . . 120.0(3) ?
C2 N1 H1A . . 120.0 ?
C14 N1 H1A . . 120.0 ?
C14 N2 C7 . . 107.0(2) ?
C14 N2 C8 . . 112.1(2) ?
C7 N2 C8 . . 116.3(2) ?
C6 C1 C2 . . 120.2(3) ?
C6 C1 C7 . . 121.4(3) ?
C2 C1 C7 . . 118.4(3) ?
N1 C2 C3 . . 121.7(3) ?
N1 C2 C1 . . 120.4(3) ?
C3 C2 C1 . . 118.0(3) ?
C4 C3 C2 . . 121.9(3) ?
C4 C3 Br1 . . 118.5(3) ?
C2 C3 Br1 . . 119.6(3) ?
C5 C4 C3 . . 118.9(3) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
C6 C5 C4 . . 121.1(3) ?
C6 C5 Br2 . . 119.3(3) ?
C4 C5 Br2 . . 119.6(3) ?
C5 C6 C1 . . 119.9(3) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
N2 C7 C1 . . 111.6(3) ?
N2 C7 H7A . . 109.3 ?
C1 C7 H7A . . 109.3 ?
N2 C7 H7B . . 109.3 ?
C1 C7 H7B . . 109.3 ?
H7A C7 H7B . . 108.0 ?
N2 C8 C9 . . 112.9(3) ?
N2 C8 C13 . . 108.8(3) ?
C9 C8 C13 . . 109.3(3) ?
N2 C8 H8 . . 108.6 ?
C9 C8 H8 . . 108.6 ?
C13 C8 H8 . . 108.6 ?
C8 C9 C10 . . 112.0(3) ?
C8 C9 H9A . . 109.2 ?
C10 C9 H9A . . 109.2 ?
C8 C9 H9B . . 109.2 ?
C10 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
C11 C10 C9 . . 112.0(3) ?
C11 C10 H10A . . 109.2 ?
C9 C10 H10A . . 109.2 ?
C11 C10 H10B . . 109.2 ?
C9 C10 H10B . . 109.2 ?
H10A C10 H10B . . 107.9 ?
O1 C11 C10 . . 107.9(3) ?
O1 C11 C12 . . 112.8(3) ?
C10 C11 C12 . . 109.8(3) ?
O1 C11 H11 . . 108.8 ?
C10 C11 H11 . . 108.8 ?
C12 C11 H11 . . 108.8 ?
C11 C12 C13 . . 110.9(3) ?
C11 C12 H12A . . 109.5 ?
C13 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
C13 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.1 ?
C8 C13 C12 . . 112.7(3) ?
C8 C13 H13A . . 109.1 ?
C12 C13 H13A . . 109.1 ?
C8 C13 H13B . . 109.1 ?
C12 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.8 ?
N1 C14 N2 . . 113.6(3) ?
N1 C14 C15 . . 113.8(3) ?
N2 C14 C15 . . 109.0(3) ?
N1 C14 H14 . . 106.7 ?
N2 C14 H14 . . 106.7 ?
C15 C14 H14 . . 106.7 ?
C16 C15 C20 . . 118.9(3) ?
C16 C15 C14 . . 118.9(3) ?
C20 C15 C14 . . 122.1(3) ?
O2 C16 C15 . . 122.2(3) ?
O2 C16 C17 . . 116.8(3) ?
C15 C16 C17 . . 121.0(3) ?
O3 C17 C18 . . 126.0(3) ?
O3 C17 C16 . . 114.9(3) ?
C18 C17 C16 . . 119.1(4) ?
C17 C18 C19 . . 120.2(4) ?
C17 C18 H18 . . 119.9 ?
C19 C18 H18 . . 119.9 ?
C20 C19 C18 . . 120.1(4) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C19 C20 C15 . . 120.6(4) ?
C19 C20 H20 . . 119.7 ?
C15 C20 H20 . . 119.7 ?
O3 C21 H21A . . 109.5 ?
O3 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O3 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
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 C3 . 1.900(3) ?
Br2 C5 . 1.895(3) ?
O1 C11 . 1.423(4) ?
O1 H1 . 0.8200 ?
O2 C16 . 1.364(4) ?
O2 H2 . 0.8200 ?
O3 C17 . 1.363(4) ?
O3 C21 . 1.416(4) ?
N1 C2 . 1.381(4) ?
N1 C14 . 1.448(4) ?
N1 H1A . 0.8600 ?
N2 C14 . 1.476(4) ?
N2 C7 . 1.482(4) ?
N2 C8 . 1.490(4) ?
C1 C6 . 1.389(4) ?
C1 C2 . 1.396(4) ?
C1 C7 . 1.517(4) ?
C2 C3 . 1.395(5) ?
C3 C4 . 1.376(4) ?
C4 C5 . 1.376(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.374(5) ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.513(5) ?
C8 C13 . 1.518(4) ?
C8 H8 . 0.9800 ?
C9 C10 . 1.514(5) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.499(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.509(5) ?
C11 H11 . 0.9800 ?
C12 C13 . 1.520(5) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.535(4) ?
C14 H14 . 0.9800 ?
C15 C16 . 1.385(5) ?
C15 C20 . 1.388(5) ?
C16 C17 . 1.397(5) ?
C17 C18 . 1.381(5) ?
C18 C19 . 1.391(6) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.379(5) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
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
O2 H2 N2 . 0.82 1.89 2.614(3) 146.5
O1 H1 O3 2_675 0.82 2.41 3.048(4) 135.3
O1 H1 O2 2_675 0.82 2.13 2.897(4) 154.6
