#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/50/2225083.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_2225083
loop_
_publ_author_name
'Li, De-Liang'
'Wu, Yang'
'Wang, Qiang'
'He, Gu'
'Yu, Luo-Ting'
_publ_section_title
;
 N⁴-(3-Bromophenyl)quinazoline-4,6-diamine
;
_journal_coeditor_code           PB2020
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o447
_journal_paper_doi               10.1107/S1600536810002631
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H11 Br N4'
_chemical_formula_moiety         'C14 H11 Br N4'
_chemical_formula_sum            'C14 H11 Br N4'
_chemical_formula_weight         315.18
_chemical_name_systematic
;
N⁴-(3-Bromophenyl)quinazoline-4,6-diamine
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                110.24(3)
_cell_angle_beta                 96.79(3)
_cell_angle_gamma                96.75(3)
_cell_formula_units_Z            4
_cell_length_a                   7.5579(15)
_cell_length_b                   11.743(2)
_cell_length_c                   15.554(3)
_cell_measurement_reflns_used    3726
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.90
_cell_volume                     1267.4(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0803
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10616
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    3.234
_exptl_absorpt_correction_T_max  0.5234
_exptl_absorpt_correction_T_min  0.3889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[SADABS (Sheldrick, 1996) using a modified Dwiggins (1975) procedure]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         1.419
_refine_diff_density_min         -1.542
_refine_ls_extinction_coef       0.0265(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0433
_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)+(0.0520P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                3735
_reflns_number_total             5931
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            pb2020.cif
_cod_data_source_block           I
_cod_original_cell_volume        1267.4(4)
_cod_database_code               2225083
_cod_database_fobs_code          2225083
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 0.32081(4) 0.54984(3) 0.19450(3) 0.02528(13) Uani d . 1 . .
N N1 0.7074(3) 0.7482(2) 0.01210(19) 0.0175(6) Uani d . 1 . .
H H1N 0.622(5) 0.800(4) 0.026(3) 0.036(11) Uiso d . 1 . .
N N2 0.9911(3) 0.7443(2) -0.03199(19) 0.0176(6) Uani d . 1 . .
N N3 1.0997(3) 0.8702(2) -0.11423(19) 0.0175(6) Uani d . 1 . .
N N4 0.4365(3) 1.0316(2) -0.13941(19) 0.0184(6) Uani d . 1 . .
H H4A 0.3481 1.0082 -0.1139 0.022 Uiso calc R 1 . .
H H4B 0.4225 1.0832 -0.1684 0.022 Uiso calc R 1 . .
C C1 0.5318(4) 0.5673(3) 0.1418(2) 0.0179(7) Uani d . 1 . .
C C2 0.6659(4) 0.4991(3) 0.1522(2) 0.0204(7) Uani d . 1 . .
H H2 0.6528 0.4433 0.1839 0.024 Uiso calc R 1 . .
C C3 0.8198(4) 0.5164(3) 0.1143(2) 0.0198(7) Uani d . 1 . .
H H3 0.9136 0.4711 0.1204 0.024 Uiso calc R 1 . .
C C4 0.8412(4) 0.5974(3) 0.0679(2) 0.0180(7) Uani d . 1 . .
H H4 0.9484 0.6074 0.0431 0.022 Uiso calc R 1 . .
C C5 0.7044(4) 0.6642(3) 0.0580(2) 0.0164(7) Uani d . 1 . .
C C6 0.5474(4) 0.6477(3) 0.0953(2) 0.0167(7) Uani d . 1 . .
H H6 0.4524 0.6918 0.0885 0.020 Uiso calc R 1 . .
C C7 0.8344(4) 0.7850(3) -0.0327(2) 0.0158(7) Uani d . 1 . .
C C8 1.1141(4) 0.7914(3) -0.0728(2) 0.0182(7) Uani d . 1 . .
H H8 1.2267 0.7632 -0.0710 0.022 Uiso calc R 1 . .
C C9 0.9338(4) 0.9078(3) -0.1195(2) 0.0151(6) Uani d . 1 . .
C C10 0.7933(4) 0.8659(3) -0.0804(2) 0.0149(6) Uani d . 1 . .
C C11 0.6255(4) 0.9061(3) -0.0889(2) 0.0166(7) Uani d . 1 . .
H H11 0.5295 0.8771 -0.0633 0.020 Uiso calc R 1 . .
C C12 0.5995(4) 0.9869(3) -0.1338(2) 0.0154(7) Uani d . 1 . .
C C13 0.7425(4) 1.0290(3) -0.1721(2) 0.0196(7) Uani d . 1 . .
H H13 0.7256 1.0854 -0.2026 0.024 Uiso calc R 1 . .
C C14 0.9041(4) 0.9895(3) -0.1658(2) 0.0191(7) Uani d . 1 . .
H H14 0.9980 1.0175 -0.1929 0.023 Uiso calc R 1 . .
Br Br2 0.47743(6) 0.69252(4) 0.64544(4) 0.05308(17) Uani d . 1 . .
N N5 0.0018(4) 0.2805(3) 0.5104(2) 0.0236(7) Uani d . 1 . .
H H5N -0.105(6) 0.250(4) 0.497(3) 0.062(16) Uiso d . 1 . .
N N6 0.2839(4) 0.2212(3) 0.5094(2) 0.0225(6) Uani d . 1 . .
N N7 0.3236(3) 0.0159(3) 0.4224(2) 0.0220(6) Uani d . 1 . .
N N8 -0.4215(4) -0.1290(3) 0.3066(2) 0.0208(6) Uani d . 1 . .
H H8N1 -0.470(5) -0.207(4) 0.292(3) 0.031(11) Uiso d . 1 . .
H H8N2 -0.467(5) -0.080(4) 0.339(3) 0.029(12) Uiso d . 1 . .
C C15 0.2510(5) 0.5963(3) 0.6368(3) 0.0297(8) Uani d . 1 . .
C C16 0.1242(5) 0.6528(4) 0.6842(3) 0.0345(9) Uani d . 1 . .
H H16 0.1503 0.7376 0.7228 0.041 Uiso calc R 1 . .
C C17 -0.0417(5) 0.5833(4) 0.6743(3) 0.0353(9) Uani d . 1 . .
H H17 -0.1317 0.6202 0.7067 0.042 Uiso calc R 1 . .
C C18 -0.0788(5) 0.4601(3) 0.6177(3) 0.0294(8) Uani d . 1 . .
H H18 -0.1943 0.4132 0.6112 0.035 Uiso calc R 1 . .
C C19 0.0523(5) 0.4039(3) 0.5700(2) 0.0237(8) Uani d . 1 . .
C C20 0.2198(5) 0.4734(3) 0.5799(3) 0.0270(8) Uani d . 1 . .
H H20 0.3112 0.4375 0.5483 0.032 Uiso calc R 1 . .
C C21 0.1078(4) 0.1919(3) 0.4798(2) 0.0200(7) Uani d . 1 . .
C C22 0.3821(4) 0.1307(3) 0.4780(2) 0.0237(8) Uani d . 1 . .
H H22 0.5091 0.1530 0.4988 0.028 Uiso calc R 1 . .
C C23 0.1403(4) -0.0162(3) 0.3923(2) 0.0176(7) Uani d . 1 . .
C C24 0.0232(4) 0.0702(3) 0.4192(2) 0.0179(7) Uani d . 1 . .
C C25 -0.1655(4) 0.0310(3) 0.3887(2) 0.0209(7) Uani d . 1 . .
H H25 -0.2446 0.0894 0.4047 0.025 Uiso calc R 1 . .
C C26 -0.2359(4) -0.0901(3) 0.3363(2) 0.0200(7) Uani d . 1 . .
C C27 -0.1169(4) -0.1752(3) 0.3086(2) 0.0208(7) Uani d . 1 . .
H H27 -0.1645 -0.2585 0.2707 0.025 Uiso calc R 1 . .
C C28 0.0670(4) -0.1386(3) 0.3358(2) 0.0209(7) Uani d . 1 . .
H H28 0.1452 -0.1968 0.3162 0.025 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'
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
C7 N1 C5 . . 131.2(2) ?
C7 N1 H1N . . 114(2) ?
C5 N1 H1N . . 113(2) ?
C7 N2 C8 . . 115.9(2) ?
C8 N3 C9 . . 115.2(3) ?
C12 N4 H4A . . 120.0 ?
C12 N4 H4B . . 120.0 ?
H4A N4 H4B . . 120.0 ?
C6 C1 C2 . . 122.4(3) ?
C6 C1 Br1 . . 118.8(2) ?
C2 C1 Br1 . . 118.8(2) ?
C1 C2 C3 . . 117.0(3) ?
C1 C2 H2 . . 121.5 ?
C3 C2 H2 . . 121.5 ?
C4 C3 C2 . . 122.3(3) ?
C4 C3 H3 . . 118.9 ?
C2 C3 H3 . . 118.9 ?
C3 C4 C5 . . 119.5(3) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C4 C5 C6 . . 119.1(3) ?
C4 C5 N1 . . 125.6(3) ?
C6 C5 N1 . . 115.3(3) ?
C1 C6 C5 . . 119.6(3) ?
C1 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
N2 C7 N1 . . 119.6(3) ?
N2 C7 C10 . . 121.8(3) ?
N1 C7 C10 . . 118.6(2) ?
N3 C8 N2 . . 129.1(3) ?
N3 C8 H8 . . 115.4 ?
N2 C8 H8 . . 115.4 ?
N3 C9 C10 . . 121.7(3) ?
N3 C9 C14 . . 119.1(3) ?
C10 C9 C14 . . 119.1(3) ?
C9 C10 C11 . . 119.4(3) ?
C9 C10 C7 . . 116.1(2) ?
C11 C10 C7 . . 124.6(3) ?
C12 C11 C10 . . 120.6(3) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C11 C12 N4 . . 121.3(3) ?
C11 C12 C13 . . 119.4(3) ?
N4 C12 C13 . . 119.2(3) ?
C14 C13 C12 . . 120.7(3) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C9 . . 120.8(3) ?
C13 C14 H14 . . 119.6 ?
C9 C14 H14 . . 119.6 ?
C21 N5 C19 . . 129.5(3) ?
C21 N5 H5N . . 111(3) ?
C19 N5 H5N . . 119(3) ?
C21 N6 C22 . . 116.5(3) ?
C22 N7 C23 . . 116.0(3) ?
C26 N8 H8N1 . . 121(2) ?
C26 N8 H8N2 . . 106(3) ?
H8N1 N8 H8N2 . . 117(4) ?
C16 C15 C20 . . 123.2(4) ?
C16 C15 Br2 . . 118.7(3) ?
C20 C15 Br2 . . 118.1(3) ?
C15 C16 C17 . . 118.1(4) ?
C15 C16 H16 . . 121.0 ?
C17 C16 H16 . . 121.0 ?
C16 C17 C18 . . 120.6(4) ?
C16 C17 H17 . . 119.7 ?
C18 C17 H17 . . 119.7 ?
C17 C18 C19 . . 120.5(4) ?
C17 C18 H18 . . 119.7 ?
C19 C18 H18 . . 119.7 ?
C20 C19 C18 . . 119.1(3) ?
C20 C19 N5 . . 123.6(3) ?
C18 C19 N5 . . 117.2(3) ?
C15 C20 C19 . . 118.5(3) ?
C15 C20 H20 . . 120.7 ?
C19 C20 H20 . . 120.7 ?
N6 C21 N5 . . 118.7(3) ?
N6 C21 C24 . . 122.1(3) ?
N5 C21 C24 . . 119.1(3) ?
N7 C22 N6 . . 128.0(3) ?
N7 C22 H22 . . 116.0 ?
N6 C22 H22 . . 116.0 ?
N7 C23 C28 . . 119.3(3) ?
N7 C23 C24 . . 121.5(3) ?
C28 C23 C24 . . 119.2(3) ?
C23 C24 C25 . . 119.2(3) ?
C23 C24 C21 . . 115.8(3) ?
C25 C24 C21 . . 125.0(3) ?
C26 C25 C24 . . 121.0(3) ?
C26 C25 H25 . . 119.5 ?
C24 C25 H25 . . 119.5 ?
C25 C26 N8 . . 121.1(3) ?
C25 C26 C27 . . 119.2(3) ?
N8 C26 C27 . . 119.6(3) ?
C28 C27 C26 . . 120.7(3) ?
C28 C27 H27 . . 119.7 ?
C26 C27 H27 . . 119.7 ?
C27 C28 C23 . . 120.7(3) ?
C27 C28 H28 . . 119.7 ?
C23 C28 H28 . . 119.7 ?
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 C1 . 1.899(3) ?
N1 C7 . 1.365(4) ?
N1 C5 . 1.403(4) ?
N1 H1N . 0.93(4) ?
N2 C7 . 1.328(4) ?
N2 C8 . 1.354(4) ?
N3 C8 . 1.305(4) ?
N3 C9 . 1.380(4) ?
N4 C12 . 1.400(4) ?
N4 H4A . 0.8800 ?
N4 H4B . 0.8800 ?
C1 C6 . 1.377(4) ?
C1 C2 . 1.391(4) ?
C2 C3 . 1.390(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.384(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.395(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.403(4) ?
C6 H6 . 0.9500 ?
C7 C10 . 1.433(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.406(4) ?
C9 C14 . 1.407(4) ?
C10 C11 . 1.412(4) ?
C11 C12 . 1.378(4) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.414(4) ?
C13 C14 . 1.362(4) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
Br2 C15 . 1.900(4) ?
N5 C21 . 1.376(4) ?
N5 C19 . 1.401(5) ?
N5 H5N . 0.82(4) ?
N6 C21 . 1.319(4) ?
N6 C22 . 1.353(4) ?
N7 C22 . 1.313(4) ?
N7 C23 . 1.372(4) ?
N8 C26 . 1.392(4) ?
N8 H8N1 . 0.89(4) ?
N8 H8N2 . 0.77(4) ?
C15 C16 . 1.372(5) ?
C15 C20 . 1.381(5) ?
C16 C17 . 1.374(5) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.383(5) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.399(5) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.384(5) ?
C20 H20 . 0.9500 ?
C21 C24 . 1.431(5) ?
C22 H22 . 0.9500 ?
C23 C28 . 1.402(5) ?
C23 C24 . 1.412(4) ?
C24 C25 . 1.416(4) ?
C25 C26 . 1.374(5) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.413(4) ?
C27 C28 . 1.375(4) ?
C27 H27 . 0.9500 ?
C28 H28 . 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 H1N N4 2_675 0.93(4) 2.28(4) 3.069(4) 142(3)
N4 H4A N3 1_455 0.88 2.33 3.137(4) 152.6
N4 H4B N8 2_565 0.88 2.39 3.178(4) 149.4
N8 H8N1 Br1 1_445 0.89(4) 2.88(4) 3.739(4) 163(3)
N8 H8N2 N7 1_455 0.77(4) 2.31(4) 3.053(4) 162(4)
