#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/21/2212197.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_2212197
loop_
_publ_author_name
'Bohle, D. Scott'
'Dorans, Kirsten S.'
'Fotie, Jean'
_publ_section_title
;
 trans-Bis(2-aminophenyl)diazene
;
_journal_coeditor_code           HB2260
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o889
_journal_page_last               o890
_journal_paper_doi               10.1107/S1600536807002413
_journal_volume                  63
_journal_year                    2007
_chemical_formula_moiety         'C12 H12 N4'
_chemical_formula_sum            'C12 H12 N4'
_chemical_formula_weight         212.26
_chemical_name_common            daab
_chemical_name_systematic        2,2'-diaminoazobenzene
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.357(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.278(6)
_cell_length_b                   5.8647(16)
_cell_length_c                   8.254(2)
_cell_measurement_reflns_used    157
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.32
_cell_volume                     1034.8(5)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3927
_diffrn_reflns_theta_full        25.92
_diffrn_reflns_theta_max         25.92
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Siemens, 1996)'
_exptl_crystal_colour            orange--red
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      1.32
_exptl_crystal_density_method    'flotation <b>in ????</b>'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         1003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0335
_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)+(0.0584P)²+0.6927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                929
_reflns_number_total             1003
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2260.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2212197
_cod_database_fobs_code          2212197
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_refinement_flags
_atom_site_occupancy
N N1 0.01100(4) 0.09432(15) 0.48469(11) 0.0164(3) Uani d . 1
N N2 0.06365(5) 0.48594(16) 0.41750(12) 0.0196(3) Uani d . 1
C C1 0.07248(5) 0.14153(18) 0.58466(12) 0.0154(3) Uani d . 1
C C2 0.09767(5) 0.34962(18) 0.54716(12) 0.0158(3) Uani d . 1
C C3 0.15849(5) 0.40897(19) 0.64058(14) 0.0186(3) Uani d . 1
H H3A 0.1760 0.5444 0.6170 0.022 Uiso calc R 1
C C4 0.19264(5) 0.26818(19) 0.76747(14) 0.0206(3) Uani d . 1
H H4A 0.2329 0.3104 0.8287 0.025 Uiso calc R 1
C C5 0.16749(5) 0.0628(2) 0.80508(13) 0.0204(3) Uani d . 1
H H5A 0.1907 -0.0307 0.8910 0.024 Uiso calc R 1
C C6 0.10796(5) 0.00022(18) 0.71356(13) 0.0178(3) Uani d . 1
H H6A 0.0912 -0.1367 0.7374 0.021 Uiso calc R 1
H H2B 0.0770(7) 0.627(3) 0.4141(17) 0.030(4) Uiso d . 1
H H2A 0.0230(8) 0.458(3) 0.3846(18) 0.033(4) Uiso 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
N1 0.0181(5) 0.0164(5) 0.0159(5) -0.0006(3) 0.0066(4) -0.0012(3)
N2 0.0197(5) 0.0170(5) 0.0215(5) -0.0013(4) 0.0048(4) 0.0022(4)
C1 0.0162(5) 0.0174(5) 0.0140(5) 0.0002(4) 0.0064(4) -0.0031(4)
C2 0.0188(5) 0.0160(5) 0.0146(5) 0.0020(4) 0.0079(4) -0.0021(4)
C3 0.0191(6) 0.0170(6) 0.0217(6) -0.0031(4) 0.0089(4) -0.0022(4)
C4 0.0155(5) 0.0249(6) 0.0205(6) -0.0010(4) 0.0037(4) -0.0038(4)
C5 0.0200(6) 0.0227(6) 0.0172(5) 0.0031(4) 0.0033(4) 0.0015(4)
C6 0.0210(6) 0.0166(5) 0.0171(5) -0.0003(4) 0.0077(4) 0.0000(4)
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'
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
_geom_angle_publ_flag
N1 N1 C1 5_556 114.92(11) n
C2 N2 H2B . 116.9(9) n
C2 N2 H2A . 115.0(10) n
H2B N2 H2A . 119.2(13) n
C6 C1 N1 . 124.98(10) n
C6 C1 C2 . 120.15(10) n
N1 C1 C2 . 114.87(9) n
N2 C2 C3 . 121.20(10) n
N2 C2 C1 . 120.34(10) n
C3 C2 C1 . 118.43(10) n
C4 C3 C2 . 120.63(10) n
C4 C3 H3A . 119.7 n
C2 C3 H3A . 119.7 n
C3 C4 C5 . 120.86(10) n
C3 C4 H4A . 119.6 n
C5 C4 H4A . 119.6 n
C6 C5 C4 . 119.41(10) n
C6 C5 H5A . 120.3 n
C4 C5 H5A . 120.3 n
C5 C6 C1 . 120.52(10) n
C5 C6 H6A . 119.7 n
C1 C6 H6A . 119.7 n
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
N1 N1 5_556 1.2641(18) n
N1 C1 . 1.4131(14) n
N2 C2 . 1.3792(14) n
N2 H2B . 0.884(16) n
N2 H2A . 0.884(16) n
C1 C6 . 1.4036(15) n
C1 C2 . 1.4135(15) n
C2 C3 . 1.4011(15) n
C3 C4 . 1.3816(16) n
C3 H3A . 0.9300 n
C4 C5 . 1.3999(16) n
C4 H4A . 0.9300 n
C5 C6 . 1.3783(16) n
C5 H5A . 0.9300 n
C6 H6A . 0.9300 n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A N1 0.884(18) 2.330(17) 2.7064(15) 105.7(13)
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
_geom_torsion_publ_flag
N1 N1 C1 C6 5_556 -2.03(17) n
N1 N1 C1 C2 5_556 178.34(10) n
C6 C1 C2 N2 . 178.18(9) n
N1 C1 C2 N2 . -2.17(14) n
C6 C1 C2 C3 . 0.42(15) n
N1 C1 C2 C3 . -179.93(8) n
N2 C2 C3 C4 . -178.42(9) n
C1 C2 C3 C4 . -0.68(16) n
C2 C3 C4 C5 . 0.33(16) n
C3 C4 C5 C6 . 0.29(16) n
C4 C5 C6 C1 . -0.55(16) n
N1 C1 C6 C5 . -179.42(9) n
C2 C1 C6 C5 . 0.19(16) n
