#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/24/8102429.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102429
loop_
_publ_author_name
'Jing-Jing Hu'
'Chuan-Ming Jin'
'Zhu Zhu'
'Hong-Feng Mei'
_publ_section_title
;
 Crystal structure of 1,4-bis[(2-phenylazo)imidazol- 1-yl]-butane,
 C22H22N8
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              219
_journal_volume                  224
_journal_year                    2009
_chemical_formula_moiety         'C11 H11 N4'
_chemical_formula_sum            'C11 H11 N4'
_chemical_formula_weight         199.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.572(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1850(11)
_cell_length_b                   12.9063(17)
_cell_length_c                   9.8571(13)
_cell_measurement_reflns_used    733
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.14
_cell_measurement_theta_min      2.63
_cell_volume                     1020.1(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5590
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.63
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,Sheldrick,1997
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0605
_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)+(0.0794P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1603
_reflns_number_gt                1296
_reflns_number_total             1996
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1267-2549.cff
_cod_data_source_block           080604cm
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8102429
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2480(3) 0.36695(19) 1.0805(3) 0.0577(7) Uani 1 1 d . . .
H1 H 0.1761 0.3666 0.9944 0.069 Uiso 1 1 calc R . .
C2 C 0.2679(4) 0.2788(2) 1.1621(3) 0.0679(8) Uani 1 1 d . . .
H2 H 0.2097 0.2188 1.1304 0.081 Uiso 1 1 calc R . .
C3 C 0.3727(4) 0.2792(2) 1.2895(3) 0.0721(9) Uani 1 1 d . . .
H3 H 0.3848 0.2197 1.3439 0.086 Uiso 1 1 calc R . .
C4 C 0.4593(4) 0.3669(3) 1.3363(3) 0.0782(9) Uani 1 1 d . . .
H4 H 0.5307 0.3671 1.4226 0.094 Uiso 1 1 calc R . .
C5 C 0.4408(3) 0.4555(2) 1.2555(3) 0.0662(8) Uani 1 1 d . . .
H5 H 0.4998 0.5152 1.2876 0.079 Uiso 1 1 calc R . .
C6 C 0.3358(3) 0.45542(18) 1.1281(2) 0.0473(6) Uani 1 1 d . . .
C7 C 0.2146(3) 0.64564(16) 0.8713(2) 0.0383(5) Uani 1 1 d . . .
C8 C 0.2255(3) 0.79920(18) 0.8029(2) 0.0511(6) Uani 1 1 d . . .
H8 H 0.2558 0.8684 0.7992 0.061 Uiso 1 1 calc R . .
C9 C 0.1113(3) 0.75179(16) 0.7036(2) 0.0459(6) Uani 1 1 d . . .
H9 H 0.0504 0.7810 0.6229 0.055 Uiso 1 1 calc R . .
C10 C 0.0019(3) 0.57102(16) 0.6719(2) 0.0419(6) Uani 1 1 d . . .
H10A H -0.1135 0.5936 0.6518 0.050 Uiso 1 1 calc R . .
H10B H 0.0091 0.5098 0.7299 0.050 Uiso 1 1 calc R . .
C11 C 0.0539(3) 0.54324(14) 0.5382(2) 0.0376(6) Uani 1 1 d . . .
H11A H 0.1696 0.5213 0.5578 0.045 Uiso 1 1 calc R . .
H11B H 0.0451 0.6040 0.4793 0.045 Uiso 1 1 calc R . .
N1 N 0.3241(2) 0.55225(15) 1.0561(2) 0.0504(5) Uani 1 1 d . . .
N2 N 0.2276(2) 0.55071(14) 0.93999(19) 0.0434(5) Uani 1 1 d . . .
N3 N 0.2902(2) 0.73451(14) 0.90761(19) 0.0475(5) Uani 1 1 d . . .
N4 N 0.1052(2) 0.65289(13) 0.74753(17) 0.0394(5) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.3(3) . . ?
C6 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 N1 114.9(2) . . ?
C1 C6 N1 125.1(2) . . ?
N3 C7 N4 111.79(18) . . ?
N3 C7 N2 130.3(2) . . ?
N4 C7 N2 117.85(18) . . ?
N3 C8 C9 112.4(2) . . ?
N3 C8 H8 123.8 . . ?
C9 C8 H8 123.8 . . ?
N4 C9 C8 105.04(19) . . ?
N4 C9 H9 127.5 . . ?
C8 C9 H9 127.5 . . ?
N4 C10 C11 112.45(18) . . ?
N4 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N4 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C11 111.6(2) . 3_566 ?
C10 C11 H11A 109.3 . . ?
C11 C11 H11A 109.3 3_566 . ?
C10 C11 H11B 109.3 . . ?
C11 C11 H11B 109.3 3_566 . ?
H11A C11 H11B 108.0 . . ?
N2 N1 C6 113.95(19) . . ?
N1 N2 C7 113.71(18) . . ?
C7 N3 C8 103.85(18) . . ?
C9 N4 C7 106.94(17) . . ?
C9 N4 C10 125.04(18) . . ?
C7 N4 C10 128.00(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.381(3) . ?
C1 C2 1.385(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.431(3) . ?
C7 N3 1.318(2) . ?
C7 N4 1.364(3) . ?
C7 N2 1.393(3) . ?
C8 N3 1.351(3) . ?
C8 C9 1.356(3) . ?
C8 H8 0.9300 . ?
C9 N4 1.352(3) . ?
C9 H9 0.9300 . ?
C10 N4 1.461(2) . ?
C10 C11 1.508(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C11 1.525(4) 3_566 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
N1 N2 1.254(2) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.5(4) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 N1 178.4(2) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C1 C6 N1 -178.4(2) . . . . ?
N3 C8 C9 N4 -0.5(3) . . . . ?
N4 C10 C11 C11 179.3(2) . . . 3_566 ?
C5 C6 N1 N2 -180.0(2) . . . . ?
C1 C6 N1 N2 -1.8(3) . . . . ?
C6 N1 N2 C7 179.04(17) . . . . ?
N3 C7 N2 N1 1.9(3) . . . . ?
N4 C7 N2 N1 -176.44(18) . . . . ?
N4 C7 N3 C8 0.1(2) . . . . ?
N2 C7 N3 C8 -178.4(2) . . . . ?
C9 C8 N3 C7 0.3(3) . . . . ?
C8 C9 N4 C7 0.5(2) . . . . ?
C8 C9 N4 C10 -178.3(2) . . . . ?
N3 C7 N4 C9 -0.4(2) . . . . ?
N2 C7 N4 C9 178.28(19) . . . . ?
N3 C7 N4 C10 178.36(19) . . . . ?
N2 C7 N4 C10 -3.0(3) . . . . ?
C11 C10 N4 C9 65.8(3) . . . . ?
C11 C10 N4 C7 -112.7(2) . . . . ?
