#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/31/2223169.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_2223169
loop_
_publ_author_name
'Booysen, Irvin'
'Gerber, Thomas I. A.'
'Hosten, Eric'
'Mayer, Peter'
_publ_section_title
;
 6-(2-Hydroxyphenyl)-5,6-dihydrobenzimidazolo[1,2-c]quinazolin-12-ium
 bromide ethanol solvate
;
_journal_coeditor_code           NG2630
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2216
_journal_paper_doi               10.1107/S1600536809032899
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H16 N3 O +, Br -, C2 H6 O'
_chemical_formula_moiety         'C20 H16 N3 O +, Br -, C2 H6 O'
_chemical_formula_sum            'C22 H22 Br N3 O2'
_chemical_formula_weight         440.333
_chemical_melting_point          484
_chemical_name_systematic
;
6-(2-Hydroxyphenyl)-5,6-dihydrobenzimidazolo[1,2-c]quinazolin-12-ium
bromide ethanol solvate
;
_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_block_code                C20H16N3O_Br_EtOH_no016_gerber
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_cell_angle_alpha                86.832(4)
_cell_angle_beta                 77.203(4)
_cell_angle_gamma                84.674(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3438(5)
_cell_length_b                   10.0736(5)
_cell_length_c                   10.8452(5)
_cell_measurement_reflns_used    3249
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.2452
_cell_measurement_theta_min      3.8914
_cell_volume                     990.53(9)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'PARST (Nardelli, 1995) and publCIF (Westrip, 20091)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0784
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7695
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         3.90
_exptl_absorpt_coefficient_mu    2.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.47638(13)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.348
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.842
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.842
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0344
_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)+(0.0232P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0537
_refine_ls_wR_factor_ref         0.0568
_reflns_number_gt                2664
_reflns_number_total             4004
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2630.cif
_cod_data_source_block           I
_cod_database_code               2223169
_cod_database_fobs_code          2223169
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
O O1 0.29606(17) 0.74651(15) 0.40530(15) 0.0371(4) Uani d . 1 . .
H H1 0.2997 0.7026 0.4728 0.056 Uiso calc R 1 . .
N N1 0.14604(19) 0.98882(17) 0.28625(17) 0.0320(5) Uani d . 1 . .
H H71 0.0504 1.0043 0.2930 0.038 Uiso calc R 1 . .
N N2 0.38107(18) 0.90626(17) 0.17422(16) 0.0253(4) Uani d . 1 . .
N N3 0.59036(18) 0.96092(17) 0.20465(17) 0.0281(5) Uani d . 1 . .
H H73 0.6551 0.9964 0.2378 0.034 Uiso calc R 1 . .
C C1 0.2175(2) 0.6833(2) 0.3382(2) 0.0261(5) Uani d . 1 . .
C C2 0.1706(2) 0.5575(2) 0.3723(2) 0.0314(6) Uani d . 1 . .
H H2A 0.1938 0.5116 0.4452 0.038 Uiso calc R 1 . .
C C3 0.0906(2) 0.4986(2) 0.3012(2) 0.0388(6) Uani d . 1 . .
H H3 0.0573 0.4129 0.3264 0.047 Uiso calc R 1 . .
C C4 0.0583(3) 0.5626(2) 0.1941(2) 0.0394(6) Uani d . 1 . .
H H4 0.0040 0.5211 0.1447 0.047 Uiso calc R 1 . .
C C5 0.1056(2) 0.6874(2) 0.1593(2) 0.0324(6) Uani d . 1 . .
H H5 0.0842 0.7313 0.0848 0.039 Uiso calc R 1 . .
C C6 0.1839(2) 0.7507(2) 0.2306(2) 0.0243(5) Uani d . 1 . .
C C7 0.2219(2) 0.8922(2) 0.1944(2) 0.0248(5) Uani d . 1 . .
H H7 0.1918 0.9171 0.1127 0.030 Uiso calc R 1 . .
C C8 0.2073(2) 1.0582(2) 0.3632(2) 0.0268(5) Uani d . 1 . .
C C9 0.1194(2) 1.1389(2) 0.4568(2) 0.0339(6) Uani d . 1 . .
H H9 0.0153 1.1454 0.4678 0.041 Uiso calc R 1 . .
C C10 0.1830(3) 1.2084(2) 0.5323(2) 0.0393(6) Uani d . 1 . .
H H10 0.1218 1.2622 0.5957 0.047 Uiso calc R 1 . .
C C11 0.3347(3) 1.2023(2) 0.5187(2) 0.0369(6) Uani d . 1 . .
H H11 0.3769 1.2511 0.5721 0.044 Uiso calc R 1 . .
C C12 0.4231(3) 1.1247(2) 0.4269(2) 0.0329(6) Uani d . 1 . .
H H12 0.5270 1.1201 0.4163 0.039 Uiso calc R 1 . .
C C13 0.3605(2) 1.0524(2) 0.3490(2) 0.0251(5) Uani d . 1 . .
C C14 0.4443(2) 0.9756(2) 0.2468(2) 0.0249(5) Uani d . 1 . .
C C15 0.4906(2) 0.8449(2) 0.0805(2) 0.0234(5) Uani d . 1 . .
C C16 0.6239(2) 0.8808(2) 0.1001(2) 0.0248(5) Uani d . 1 . .
C C17 0.7569(2) 0.8389(2) 0.0233(2) 0.0300(6) Uani d . 1 . .
H H17 0.8475 0.8646 0.0364 0.036 Uiso calc R 1 . .
C C18 0.7518(2) 0.7580(2) -0.0733(2) 0.0337(6) Uani d . 1 . .
H H18 0.8411 0.7264 -0.1280 0.040 Uiso calc R 1 . .
C C19 0.6187(3) 0.7212(2) -0.0929(2) 0.0337(6) Uani d . 1 . .
H H19 0.6199 0.6650 -0.1607 0.040 Uiso calc R 1 . .
C C20 0.4854(2) 0.7640(2) -0.0169(2) 0.0315(6) Uani d . 1 . .
H H20 0.3948 0.7391 -0.0307 0.038 Uiso calc R 1 . .
O O2 0.7042(2) 0.38247(17) 0.37419(15) 0.0512(5) Uani d . 1 . .
H H2 0.7545 0.3286 0.3219 0.077 Uiso calc R 1 . .
C C21 0.5862(3) 0.4457(3) 0.3245(3) 0.0556(8) Uani d . 1 . .
H H21A 0.5252 0.5062 0.3880 0.067 Uiso calc R 1 . .
H H21B 0.5236 0.3771 0.3092 0.067 Uiso calc R 1 . .
C C22 0.6360(3) 0.5233(3) 0.2049(3) 0.0656(9) Uani d . 1 . .
H H22A 0.7003 0.5901 0.2188 0.098 Uiso calc R 1 . .
H H22B 0.5503 0.5683 0.1774 0.098 Uiso calc R 1 . .
H H22C 0.6905 0.4630 0.1396 0.098 Uiso calc R 1 . .
Br Br1 0.85598(3) 0.14400(3) 0.18829(3) 0.04163(10) 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'
Br Br -0.2901 2.4595 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?
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
C1 O1 H1 . . 109.5 ?
C8 N1 C7 . . 126.93(17) ?
C8 N1 H71 . . 116.5 ?
C7 N1 H71 . . 116.5 ?
C14 N2 C15 . . 109.14(17) ?
C14 N2 C7 . . 125.15(18) ?
C15 N2 C7 . . 125.64(18) ?
C14 N3 C16 . . 109.31(18) ?
C14 N3 H73 . . 125.3 ?
C16 N3 H73 . . 125.3 ?
O1 C1 C2 . . 122.8(2) ?
O1 C1 C6 . . 117.34(19) ?
C2 C1 C6 . . 119.9(2) ?
C3 C2 C1 . . 120.3(2) ?
C3 C2 H2A . . 119.8 ?
C1 C2 H2A . . 119.8 ?
C2 C3 C4 . . 120.7(2) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C3 C4 C5 . . 119.2(2) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
C4 C5 C6 . . 121.5(2) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C5 C6 C1 . . 118.4(2) ?
C5 C6 C7 . . 119.27(19) ?
C1 C6 C7 . . 122.17(19) ?
N1 C7 N2 . . 107.70(17) ?
N1 C7 C6 . . 113.67(17) ?
N2 C7 C6 . . 112.43(15) ?
N1 C7 H7 . . 107.6 ?
N2 C7 H7 . . 107.6 ?
C6 C7 H7 . . 107.6 ?
N1 C8 C9 . . 121.2(2) ?
N1 C8 C13 . . 120.7(2) ?
C9 C8 C13 . . 118.2(2) ?
C10 C9 C8 . . 120.3(2) ?
C10 C9 H9 . . 119.9 ?
C8 C9 H9 . . 119.9 ?
C9 C10 C11 . . 121.6(2) ?
C9 C10 H10 . . 119.2 ?
C11 C10 H10 . . 119.2 ?
C12 C11 C10 . . 119.2(2) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C11 C12 C13 . . 120.2(2) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C12 C13 C8 . . 120.6(2) ?
C12 C13 C14 . . 123.8(2) ?
C8 C13 C14 . . 115.6(2) ?
N3 C14 N2 . . 108.79(19) ?
N3 C14 C13 . . 128.8(2) ?
N2 C14 C13 . . 122.39(19) ?
C20 C15 C16 . . 121.4(2) ?
C20 C15 N2 . . 132.57(19) ?
C16 C15 N2 . . 106.04(19) ?
C17 C16 N3 . . 131.3(2) ?
C17 C16 C15 . . 122.0(2) ?
N3 C16 C15 . . 106.71(19) ?
C18 C17 C16 . . 116.6(2) ?
C18 C17 H17 . . 121.7 ?
C16 C17 H17 . . 121.7 ?
C17 C18 C19 . . 121.6(2) ?
C17 C18 H18 . . 119.2 ?
C19 C18 H18 . . 119.2 ?
C20 C19 C18 . . 121.9(2) ?
C20 C19 H19 . . 119.0 ?
C18 C19 H19 . . 119.0 ?
C19 C20 C15 . . 116.5(2) ?
C19 C20 H20 . . 121.8 ?
C15 C20 H20 . . 121.8 ?
C21 O2 H2 . . 109.5 ?
O2 C21 C22 . . 113.1(2) ?
O2 C21 H21A . . 109.0 ?
C22 C21 H21A . . 109.0 ?
O2 C21 H21B . . 109.0 ?
C22 C21 H21B . . 109.0 ?
H21A C21 H21B . . 107.8 ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 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
O1 C1 . 1.360(2) ?
O1 H1 . 0.8400 ?
N1 C8 . 1.365(3) ?
N1 C7 . 1.452(3) ?
N1 H71 . 0.8800 ?
N2 C14 . 1.342(3) ?
N2 C15 . 1.398(3) ?
N2 C7 . 1.474(2) ?
N3 C14 . 1.336(2) ?
N3 C16 . 1.390(3) ?
N3 H73 . 0.8800 ?
C1 C2 . 1.383(3) ?
C1 C6 . 1.398(3) ?
C2 C3 . 1.376(3) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.376(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.377(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.390(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.511(3) ?
C7 H7 . 1.0000 ?
C8 C9 . 1.401(3) ?
C8 C13 . 1.402(3) ?
C9 C10 . 1.367(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.388(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.373(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.397(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.427(3) ?
C15 C20 . 1.381(3) ?
C15 C16 . 1.392(3) ?
C16 C17 . 1.379(3) ?
C17 C18 . 1.373(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.393(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.380(3) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
O2 C21 . 1.416(3) ?
O2 H2 . 0.8400 ?
C21 C22 . 1.482(3) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?
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
O1 H1 O2 2_666 0.84 1.82 2.657(2) 175.2 yes
N1 H71 Br1 1_465 0.88 2.61 3.3501(17) 141.8 yes
N3 H73 Br1 1_565 0.88 2.45 3.1956(18) 142.7 yes
O2 H2 Br1 . 0.84 2.41 3.2378(17) 167.6 yes
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 C1 C2 C3 . . . . 179.6(2) ?
C6 C1 C2 C3 . . . . -0.3(3) ?
C1 C2 C3 C4 . . . . 1.2(3) ?
C2 C3 C4 C5 . . . . -0.8(3) ?
C3 C4 C5 C6 . . . . -0.6(3) ?
C4 C5 C6 C1 . . . . 1.5(3) ?
C4 C5 C6 C7 . . . . -174.82(19) ?
O1 C1 C6 C5 . . . . 179.06(19) ?
C2 C1 C6 C5 . . . . -1.0(3) ?
O1 C1 C6 C7 . . . . -4.7(3) ?
C2 C1 C6 C7 . . . . 175.17(19) ?
C8 N1 C7 N2 . . . . -14.3(3) ?
C8 N1 C7 C6 . . . . 110.9(2) ?
C14 N2 C7 N1 . . . . 12.6(3) ?
C15 N2 C7 N1 . . . . -170.59(17) ?
C14 N2 C7 C6 . . . . -113.4(2) ?
C15 N2 C7 C6 . . . . 63.4(2) ?
C5 C6 C7 N1 . . . . 112.5(2) ?
C1 C6 C7 N1 . . . . -63.7(2) ?
C5 C6 C7 N2 . . . . -124.8(2) ?
C1 C6 C7 N2 . . . . 59.0(3) ?
C7 N1 C8 C9 . . . . -173.6(2) ?
C7 N1 C8 C13 . . . . 7.6(3) ?
N1 C8 C9 C10 . . . . -179.5(2) ?
C13 C8 C9 C10 . . . . -0.7(3) ?
C8 C9 C10 C11 . . . . 0.4(3) ?
C9 C10 C11 C12 . . . . 0.1(3) ?
C10 C11 C12 C13 . . . . -0.4(3) ?
C11 C12 C13 C8 . . . . 0.1(3) ?
C11 C12 C13 C14 . . . . 176.3(2) ?
N1 C8 C13 C12 . . . . 179.27(19) ?
C9 C8 C13 C12 . . . . 0.4(3) ?
N1 C8 C13 C14 . . . . 2.8(3) ?
C9 C8 C13 C14 . . . . -176.06(19) ?
C16 N3 C14 N2 . . . . 0.7(2) ?
C16 N3 C14 C13 . . . . -177.9(2) ?
C15 N2 C14 N3 . . . . -0.4(2) ?
C7 N2 C14 N3 . . . . 176.86(17) ?
C15 N2 C14 C13 . . . . 178.27(18) ?
C7 N2 C14 C13 . . . . -4.4(3) ?
C12 C13 C14 N3 . . . . -2.1(3) ?
C8 C13 C14 N3 . . . . 174.23(19) ?
C12 C13 C14 N2 . . . . 179.4(2) ?
C8 C13 C14 N2 . . . . -4.2(3) ?
C14 N2 C15 C20 . . . . -179.8(2) ?
C7 N2 C15 C20 . . . . 2.9(4) ?
C14 N2 C15 C16 . . . . -0.1(2) ?
C7 N2 C15 C16 . . . . -177.31(17) ?
C14 N3 C16 C17 . . . . 178.9(2) ?
C14 N3 C16 C15 . . . . -0.8(2) ?
C20 C15 C16 C17 . . . . 0.6(3) ?
N2 C15 C16 C17 . . . . -179.22(19) ?
C20 C15 C16 N3 . . . . -179.71(19) ?
N2 C15 C16 N3 . . . . 0.5(2) ?
N3 C16 C17 C18 . . . . 179.6(2) ?
C15 C16 C17 C18 . . . . -0.8(3) ?
C16 C17 C18 C19 . . . . 0.5(3) ?
C17 C18 C19 C20 . . . . 0.1(3) ?
C18 C19 C20 C15 . . . . -0.3(3) ?
C16 C15 C20 C19 . . . . 0.0(3) ?
N2 C15 C20 C19 . . . . 179.8(2) ?
