#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/97/2239793.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_2239793
loop_
_publ_author_name
'Kautny, Paul'
'Fröhlich, Johannes'
'Stöger, Berthold'
'Weil, Matthias'
_publ_section_title
;
 Isotypic crystal structures of
 2,6-dibromo-N,N-bis(4-nitrophenyl)aniline and
 2,6-dichloro-N,N-bis(4-nitrophenyl)aniline
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              65
_journal_page_last               67
_journal_paper_doi               10.1107/S1600536814010964
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C18 H11 Br2 N3 O4'
_chemical_formula_moiety         'C18 H11 Br2 N3 O4'
_chemical_formula_sum            'C18 H11 Br2 N3 O4'
_chemical_formula_weight         493.1
_chemical_name_systematic
;
2,6-Dibromo-N,N-bis(4-nitrophenyl)aniline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 107.576(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4705(7)
_cell_length_b                   11.6686(6)
_cell_length_c                   11.7081(7)
_cell_measurement_reflns_used    9998
_cell_measurement_temperature    100
_cell_measurement_theta_max      34.9
_cell_measurement_theta_min      2.9
_cell_volume                     1754.39(17)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2013)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement
'JANA2006 (Petříček, et al., 2006)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            52187
_diffrn_reflns_theta_full        35.06
_diffrn_reflns_theta_max         35.06
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    4.652
_exptl_absorpt_correction_T_max  0.390
_exptl_absorpt_correction_T_min  0.055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            'translucent yellow'
_exptl_crystal_density_diffrn    1.8663
_exptl_crystal_description       'triangular prism'
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.00
_refine_diff_density_min         -0.91
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.36
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_constraints    44
_refine_ls_number_parameters     244
_refine_ls_number_reflns         7731
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.0072
_refine_ls_shift/su_mean         0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(σ²(I)+0.0009I²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                5557
_reflns_number_total             7731
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            su0003sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2ycb'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239793
_cod_database_fobs_code          2239793
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
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
Br Br1 0.573900(13) 0.859367(14) 0.064003(15) 0.01908(5) Uani d 1
Br Br2 0.901801(14) 1.107097(16) 0.387459(16) 0.02362(6) Uani d 1
O O1 0.60098(10) 1.55865(11) 0.07605(12) 0.0242(4) Uani d 1
O O2 0.52588(11) 1.50312(11) 0.20583(12) 0.0258(4) Uani d 1
O O3 0.89116(11) 0.84226(12) -0.27898(11) 0.0275(5) Uani d 1
O O4 1.01356(11) 0.77627(12) -0.12917(12) 0.0279(5) Uani d 1
N N1 0.74647(10) 1.04271(11) 0.14278(11) 0.0116(4) Uani d 1
N N2 0.57864(11) 1.48465(12) 0.13859(12) 0.0169(4) Uani d 1
N N3 0.93586(11) 0.83519(12) -0.17142(12) 0.0166(4) Uani d 1
C C1 0.74189(12) 0.96819(13) 0.23780(13) 0.0119(4) Uani d 1
C C2 0.67254(13) 0.87583(13) 0.21625(15) 0.0146(5) Uani d 1
C C3 0.67200(13) 0.79887(15) 0.30661(16) 0.0199(5) Uani d 1
C C4 0.73845(14) 0.81727(16) 0.42090(16) 0.0225(6) Uani d 1
C C5 0.80581(14) 0.90916(15) 0.44579(15) 0.0191(5) Uani d 1
C C6 0.80787(13) 0.98333(13) 0.35429(14) 0.0150(5) Uani d 1
C C7 0.70196(12) 1.15186(12) 0.13580(13) 0.0108(4) Uani d 1
C C8 0.72745(13) 1.24028(13) 0.06810(14) 0.0143(5) Uani d 1
C C9 0.68543(13) 1.34821(13) 0.06712(14) 0.0150(5) Uani d 1
C C10 0.61940(12) 1.36934(13) 0.13585(14) 0.0132(4) Uani d 1
C C11 0.59367(12) 1.28422(13) 0.20434(14) 0.0132(4) Uani d 1
C C12 0.63388(12) 1.17542(13) 0.20293(13) 0.0128(4) Uani d 1
C C13 0.79772(12) 0.99930(12) 0.06341(13) 0.0114(4) Uani d 1
C C14 0.75857(13) 1.01765(14) -0.06029(13) 0.0153(5) Uani d 1
C C15 0.80630(13) 0.96656(14) -0.13642(14) 0.0158(5) Uani d 1
C C16 0.89197(12) 0.89691(13) -0.08923(13) 0.0126(4) Uani d 1
C C17 0.93330(12) 0.87926(13) 0.03259(14) 0.0138(4) Uani d 1
C C18 0.88567(12) 0.93065(13) 0.10882(13) 0.0129(4) Uani d 1
H H1c3 0.62618 0.733863 0.289983 0.0239 Uiso d 1
H H1c4 0.737607 0.765079 0.483986 0.027 Uiso d 1
H H1c5 0.850818 0.921597 0.525706 0.023 Uiso d 1
H H1c8 0.774364 1.225481 0.02228 0.0171 Uiso d 1
H H1c9 0.701637 1.408126 0.019449 0.018 Uiso d 1
H H1c11 0.548604 1.300523 0.252057 0.0158 Uiso d 1
H H1c12 0.615028 1.115297 0.248386 0.0154 Uiso d 1
H H1c14 0.698685 1.065633 -0.092153 0.0183 Uiso d 1
H H1c15 0.780239 0.979303 -0.221267 0.0189 Uiso d 1
H H1c17 0.993928 0.83222 0.063785 0.0165 Uiso d 1
H H1c18 0.913367 0.918984 0.19371 0.0154 Uiso d 1
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Br -0.2901 2.4595 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 Br1 C2 52.74(6)
N1 Br2 C6 52.88(5)
Br1 N1 Br2 133.15(5)
Br1 N1 C1 66.74(7)
Br1 N1 C7 110.03(9)
Br1 N1 C13 91.63(8)
Br2 N1 C1 66.54(7)
Br2 N1 C7 89.49(8)
Br2 N1 C13 111.71(8)
C1 N1 C7 118.76(14)
C1 N1 C13 116.10(12)
C7 N1 C13 125.13(13)
O1 N2 O2 123.55(15)
O1 N2 C10 118.34(16)
O2 N2 C10 118.09(14)
O3 N3 O4 123.27(16)
O3 N3 C16 118.22(14)
O4 N3 C16 118.47(13)
N1 C1 C2 120.82(12)
N1 C1 C6 121.30(13)
C2 C1 C6 117.86(15)
Br1 C2 C1 119.42(12)
Br1 C2 C3 119.35(12)
C1 C2 C3 121.17(14)
C2 C3 C4 119.04(16)
C2 C3 H1c3 120.48
C4 C3 H1c3 120.48
C3 C4 C5 121.18(17)
C3 C4 H1c4 119.41
C5 C4 H1c4 119.41
C4 C5 C6 119.27(14)
C4 C5 H1c5 120.37
C6 C5 H1c5 120.37
Br2 C6 C1 119.26(12)
Br2 C6 C5 119.31(11)
C1 C6 C5 121.42(15)
N1 C7 C8 121.85(16)
N1 C7 C12 119.11(14)
C8 C7 C12 118.97(14)
C7 C8 C9 120.36(17)
C7 C8 H1c8 119.82
C9 C8 H1c8 119.82
C8 C9 C10 119.34(16)
C8 C9 H1c9 120.33
C10 C9 H1c9 120.33
N2 C10 C9 119.20(15)
N2 C10 C11 119.18(16)
C9 C10 C11 121.60(15)
C10 C11 C12 118.96(16)
C10 C11 H1c11 120.52
C12 C11 H1c11 120.52
C7 C12 C11 120.75(15)
C7 C12 H1c12 119.63
C11 C12 H1c12 119.62
N1 C13 C14 121.39(13)
N1 C13 C18 118.94(13)
C14 C13 C18 119.55(16)
C13 C14 C15 119.86(14)
C13 C14 H1c14 120.07
C15 C14 H1c14 120.07
C14 C15 C16 119.38(14)
C14 C15 H1c15 120.31
C16 C15 H1c15 120.31
N3 C16 C15 118.75(13)
N3 C16 C17 119.29(14)
C15 C16 C17 121.85(16)
C16 C17 C18 118.74(14)
C16 C17 H1c17 120.63
C18 C17 H1c17 120.63
C13 C18 C17 120.58(14)
C13 C18 H1c18 119.71
C17 C18 H1c18 119.71
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 N1 3.0882(13)
Br1 C2 1.8840(15)
Br2 N1 3.0869(12)
Br2 C6 1.8817(16)
O1 N2 1.227(2)
O2 N2 1.228(2)
O3 N3 1.2237(17)
O4 N3 1.2247(19)
N1 C1 1.428(2)
N1 C7 1.3995(19)
N1 C13 1.409(2)
N2 C10 1.457(2)
N3 C16 1.462(2)
C1 C2 1.398(2)
C1 C6 1.396(2)
C2 C3 1.389(3)
C3 C4 1.384(2)
C3 H1c3 0.96
C4 C5 1.378(3)
C4 H1c4 0.96
C5 C6 1.384(2)
C5 H1c5 0.96
C7 C8 1.405(2)
C7 C12 1.403(3)
C8 C9 1.379(2)
C8 H1c8 0.96
C9 C10 1.390(3)
C9 H1c9 0.96
C10 C11 1.385(2)
C11 C12 1.382(2)
C11 H1c11 0.96
C12 H1c12 0.96
C13 C14 1.400(2)
C13 C18 1.396(2)
C14 C15 1.382(3)
C14 H1c14 0.96
C15 C16 1.383(2)
C15 H1c15 0.96
C16 C17 1.381(2)
C17 C18 1.383(3)
C17 H1c17 0.96
C18 H1c18 0.96
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
C5 H1C5 O3 1_556 0.96 2.37 3.175(2) 141
C12 H1C12 O2 2_645 0.96 2.49 3.347(2) 148
