#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/38/2233885.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_2233885
loop_
_publ_author_name
'Seidel, Nadine'
'Seichter, Wilhelm'
'Weber, Edwin'
_publ_section_title
;
 1,5-Diamino-2,6-dibromo-9,10-anthraquinone
;
_journal_coeditor_code           IM2352
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o838
_journal_paper_doi               10.1107/S1600536812004229
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H8 Br2 N2 O2'
_chemical_formula_moiety         'C14 H8 Br2 N2 O2'
_chemical_formula_sum            'C14 H8 Br2 N2 O2'
_chemical_formula_weight         396.04
_chemical_name_systematic
;
1,5-Diamino-2,6-dibromo-9,10-anthraquinone
;
_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           SHELXL97
_cell_angle_alpha                94.455(2)
_cell_angle_beta                 99.970(2)
_cell_angle_gamma                100.859(2)
_cell_formula_units_Z            1
_cell_length_a                   4.41770(10)
_cell_length_b                   6.2240(2)
_cell_length_c                   11.8410(3)
_cell_measurement_reflns_used    5166
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      38.80
_cell_measurement_theta_min      3.18
_cell_volume                     312.865(15)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7769
_diffrn_reflns_theta_full        31.09
_diffrn_reflns_theta_max         31.09
_diffrn_reflns_theta_min         3.35
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    6.479
_exptl_absorpt_correction_T_max  0.7592
_exptl_absorpt_correction_T_min  0.1170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.102
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.634
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         2003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0256
_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)+(0.0454P)²+0.2515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0713
_reflns_number_gt                1844
_reflns_number_total             2003
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2352.cif
_cod_data_source_block           I
_cod_database_code               2233885
_cod_database_fobs_code          2233885
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_symmetry_multiplicity
Br Br1 0.18844(5) 0.30597(3) 0.572710(15) 0.02812(8) Uani d . 1 1
O O1 0.1853(3) 0.3189(2) 1.04118(13) 0.0228(3) Uani d . 1 1
N N1 0.1114(4) 0.3920(3) 0.82251(13) 0.0197(3) Uani d . 1 1
H H1A 0.0439 0.4563 0.7622 0.024 Uiso calc R 1 1
H H1B 0.0777 0.4351 0.8910 0.024 Uiso calc R 1 1
C C1 0.3215(4) 0.1566(3) 0.69978(14) 0.0184(3) Uani d . 1 1
C C2 0.4697(4) -0.0157(3) 0.68165(15) 0.0205(3) Uani d . 1 1
H H2 0.4972 -0.0606 0.6062 0.025 Uiso calc R 1 1
C C3 0.5785(4) -0.1235(3) 0.77398(15) 0.0188(3) Uani d . 1 1
H H3 0.6811 -0.2421 0.7618 0.023 Uiso calc R 1 1
C C4 0.5371(4) -0.0574(3) 0.88430(14) 0.0152(3) Uani d . 1 1
C C5 0.3340(4) 0.1755(3) 1.02023(15) 0.0159(3) Uani d . 1 1
C C6 0.3806(4) 0.1154(3) 0.90319(14) 0.0145(3) Uani d . 1 1
C C7 0.2662(4) 0.2273(3) 0.80995(14) 0.0158(3) Uani d . 1 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_3
_geom_angle
C7 N1 H1A . 120.0
C7 N1 H1B . 120.0
H1A N1 H1B . 120.0
C2 C1 C7 . 122.64(16)
C2 C1 Br1 . 118.66(13)
C7 C1 Br1 . 118.69(13)
C1 C2 C3 . 119.84(16)
C1 C2 H2 . 120.1
C3 C2 H2 . 120.1
C2 C3 C4 . 119.87(16)
C2 C3 H3 . 120.1
C4 C3 H3 . 120.1
C3 C4 C6 . 120.66(16)
C3 C4 C5 2_657 117.24(15)
C6 C4 C5 2_657 122.10(15)
O1 C5 C6 . 121.83(16)
O1 C5 C4 2_657 119.18(16)
C6 C5 C4 2_657 118.98(15)
C4 C6 C7 . 120.42(15)
C4 C6 C5 . 118.89(15)
C7 C6 C5 . 120.69(15)
N1 C7 C1 . 120.38(16)
N1 C7 C6 . 123.08(15)
C1 C7 C6 . 116.54(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C1 . 1.8949(18)
O1 C5 . 1.238(2)
N1 C7 . 1.348(2)
N1 H1A . 0.8800
N1 H1B . 0.8800
C1 C2 . 1.379(3)
C1 C7 . 1.420(2)
C2 C3 . 1.389(3)
C2 H2 . 0.9500
C3 C4 . 1.392(2)
C3 H3 . 0.9500
C4 C6 . 1.407(2)
C5 C6 . 1.467(2)
C5 C4 2_657 1.485(2)
C6 C7 . 1.421(2)
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 H1B O1 1 0.88 1.99 2.639(2) 129.8
N1 H1A Br1 1 0.88 2.59 3.053(2) 113.7
N1 H1B O1 2_567 0.88 2.27 2.955(2) 134.9
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_4
_geom_torsion
Br1 Br1 C1 C2 1 . 0.00(9)
Br1 Br1 C1 C7 1 . 0.00(10)
C7 C1 C2 C3 . . -1.7(3)
Br1 C1 C2 C3 . . 177.95(14)
C1 C2 C3 C4 . . 0.1(3)
C2 C3 C4 C6 . . 1.1(3)
C2 C3 C4 C5 . 2_657 -178.47(16)
O1 O1 C5 C6 1 . 0.0(5)
O1 O1 C5 C4 1 2_657 0.0(6)
C3 C4 C6 C7 . . -0.9(2)
C5 C4 C6 C7 2_657 . 178.70(15)
C3 C4 C6 C5 . . 178.25(15)
C5 C4 C6 C5 2_657 . -2.2(3)
O1 C5 C6 C4 . . -176.53(16)
C4 C5 C6 C4 2_657 . 2.1(2)
O1 C5 C6 C7 . . 2.6(2)
C4 C5 C6 C7 2_657 . -178.77(14)
C2 C1 C7 N1 . . -177.84(17)
Br1 C1 C7 N1 . . 2.5(2)
C2 C1 C7 C6 . . 1.9(2)
Br1 C1 C7 C6 . . -177.76(12)
C4 C6 C7 N1 . . 179.15(16)
C5 C6 C7 N1 . . 0.0(2)
C4 C6 C7 C1 . . -0.6(2)
C5 C6 C7 C1 . . -179.71(15)
