#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/81/2218124.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_2218124
loop_
_publ_author_name
'Zhou, Tian'
'Han, De-Fu'
'Hu, Yong-Jun'
_publ_section_title
;
 4,6-Dinitrobenzene-1,3-diamine
;
_journal_coeditor_code           HB2712
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o840
_journal_paper_doi               10.1107/S1600536808009318
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C6 H6 N4 O4'
_chemical_formula_moiety         'C6 H6 N4 O4'
_chemical_formula_sum            'C6 H6 N4 O4'
_chemical_formula_weight         198.15
_chemical_name_systematic
;
4,6-Dinitrobenzene-1,3-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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                67.710(6)
_cell_angle_beta                 86.692(6)
_cell_angle_gamma                62.214(5)
_cell_formula_units_Z            2
_cell_length_a                   7.1294(6)
_cell_length_b                   7.1770(9)
_cell_length_c                   9.1289(8)
_cell_measurement_reflns_used    1322
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.09
_cell_measurement_theta_min      3.37
_cell_volume                     378.30(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_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      295(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2447
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         3.37
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0511
_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)+(0.15P)²+0.0584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1725
_refine_ls_wR_factor_ref         0.1871
_reflns_number_gt                1098
_reflns_number_total             1322
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2712.cif
_cod_data_source_block           I
_cod_database_code               2218124
_cod_database_fobs_code          2218124
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
C C1 0.2508(3) 0.6981(4) 0.8212(2) 0.0307(5) Uani d . 1
C C2 0.2639(3) 0.8653(4) 0.6845(2) 0.0325(6) Uani d . 1
H H2 0.2723 0.9844 0.6965 0.039 Uiso calc R 1
C C3 0.2654(3) 0.8654(3) 0.5319(2) 0.0291(5) Uani d . 1
C C4 0.2464(3) 0.6832(3) 0.5162(2) 0.0284(5) Uani d . 1
C C5 0.2400(3) 0.5121(3) 0.6491(2) 0.0308(5) Uani d . 1
H H5 0.2317 0.3932 0.6369 0.037 Uiso calc R 1
C C6 0.2457(3) 0.5127(3) 0.7994(2) 0.0312(5) Uani d . 1
N N1 0.2441(3) 0.7171(3) 0.9615(2) 0.0399(6) Uani d . 1
H H1A 0.2478 0.8319 0.9678 0.048 Uiso calc R 1
H H1B 0.2360 0.6146 1.0455 0.048 Uiso calc R 1
N N2 0.2856(3) 1.0298(3) 0.4091(2) 0.0397(5) Uani d . 1
H H2A 0.2977 1.1347 0.4248 0.048 Uiso calc R 1
H H2B 0.2865 1.0300 0.3148 0.048 Uiso calc R 1
N N3 0.2326(3) 0.6701(3) 0.3643(2) 0.0332(5) Uani d . 1
N N4 0.2487(3) 0.3197(3) 0.9290(2) 0.0390(5) Uani d . 1
O O1 0.2415(3) 0.8172(3) 0.24312(17) 0.0490(5) Uani d . 1
O O2 0.2106(3) 0.5129(3) 0.35769(19) 0.0501(5) Uani d . 1
O O3 0.2537(4) 0.1638(3) 0.9013(2) 0.0635(7) Uani d . 1
O O4 0.2458(3) 0.3152(3) 1.06588(18) 0.0539(6) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0380(11) 0.0317(11) 0.0225(10) -0.0169(9) 0.0053(8) -0.0108(8)
C2 0.0471(12) 0.0284(11) 0.0280(12) -0.0218(9) 0.0058(9) -0.0126(9)
C3 0.0360(11) 0.0269(11) 0.0236(10) -0.0160(8) 0.0051(8) -0.0082(8)
C4 0.0354(11) 0.0300(11) 0.0207(10) -0.0149(9) 0.0052(7) -0.0122(9)
C5 0.0401(11) 0.0256(10) 0.0287(11) -0.0172(9) 0.0043(8) -0.0112(9)
C6 0.0415(11) 0.0288(11) 0.0220(11) -0.0186(9) 0.0041(8) -0.0065(9)
N1 0.0684(13) 0.0374(11) 0.0218(10) -0.0307(10) 0.0093(8) -0.0132(8)
N2 0.0674(13) 0.0363(10) 0.0241(9) -0.0343(10) 0.0092(8) -0.0091(8)
N3 0.0443(10) 0.0319(10) 0.0253(9) -0.0185(8) 0.0041(7) -0.0129(8)
N4 0.0593(12) 0.0337(11) 0.0265(9) -0.0268(9) 0.0078(8) -0.0090(8)
O1 0.0861(13) 0.0490(11) 0.0202(8) -0.0406(9) 0.0121(7) -0.0121(8)
O2 0.0847(12) 0.0457(10) 0.0358(10) -0.0388(9) 0.0054(8) -0.0217(8)
O3 0.1255(18) 0.0439(11) 0.0397(10) -0.0569(12) 0.0171(10) -0.0147(9)
O4 0.0979(14) 0.0498(11) 0.0214(9) -0.0460(10) 0.0134(8) -0.0087(8)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 119.87(19)
N1 C1 C6 123.84(19)
C2 C1 C6 116.29(19)
C3 C2 C1 124.43(19)
C3 C2 H2 117.8
C1 C2 H2 117.8
N2 C3 C2 119.92(18)
N2 C3 C4 123.51(19)
C2 C3 C4 116.57(18)
C5 C4 C3 120.39(19)
C5 C4 N3 117.18(18)
C3 C4 N3 122.43(19)
C4 C5 C6 121.69(19)
C4 C5 H5 119.2
C6 C5 H5 119.2
C5 C6 N4 116.47(18)
C5 C6 C1 120.45(19)
N4 C6 C1 123.07(19)
C1 N1 H1A 120.0
C1 N1 H1B 120.0
H1A N1 H1B 120.0
C3 N2 H2A 120.0
C3 N2 H2B 120.0
H2A N2 H2B 120.0
O1 N3 O2 121.21(18)
O1 N3 C4 119.26(17)
O2 N3 C4 119.52(17)
O3 N4 O4 121.72(17)
O3 N4 C6 119.01(18)
O4 N4 C6 119.27(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.334(3)
C1 C2 1.401(3)
C1 C6 1.435(3)
C2 C3 1.392(3)
C2 H2 0.9300
C3 N2 1.344(3)
C3 C4 1.434(3)
C4 C5 1.377(3)
C4 N3 1.437(3)
C5 C6 1.377(3)
C5 H5 0.9300
C6 N4 1.432(3)
N1 H1A 0.8600
N1 H1B 0.8600
N2 H2A 0.8600
N2 H2B 0.8600
N3 O1 1.229(2)
N3 O2 1.233(2)
N4 O3 1.222(3)
N4 O4 1.236(3)
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 H1A O3 1_565 0.86 2.24 3.074(2) 162
N1 H1A O1 1_556 0.86 2.47 2.917(2) 113
N1 H1B O4 . 0.86 2.05 2.667(3) 128
N2 H2A O2 1_565 0.86 2.31 3.098(2) 152
N2 H2B O1 . 0.86 2.03 2.642(2) 128
N2 H2B O4 1_564 0.86 2.33 2.964(3) 131
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 257460
