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#$Date: 2022-09-20 11:24:25 +0300 (Tue, 20 Sep 2022) $
#$Revision: 277992 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/57/8105792.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_8105792
loop_
_publ_author_name
'Gao, Dong-Mei'
'Liu, Lu'
'Tang, Meng'
'He, Chunting'
'Du, Zhen-Ting'
_publ_section_title
;
 The crystal structure of
 (E)-1-(4-methoxyphenyl)-3-(2-nitrophenyl)triaz-1-ene C8H8N2O4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              597
_journal_page_last               598
_journal_paper_doi               10.1515/ncrs-2018-0234
_journal_volume                  234
_journal_year                    2019
_chemical_formula_sum            'C13 H12 N4 O3'
_chemical_formula_weight         272.27
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.393(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.748(5)
_cell_length_b                   5.6488(10)
_cell_length_c                   16.437(3)
_cell_measurement_reflns_used    3015
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.69
_cell_measurement_theta_min      2.48
_cell_volume                     2571.9(8)
_computing_cell_refinement       'Bruker SAINT [9]'
_computing_data_collection       'Bruker APEX2 [8]'
_computing_data_reduction        'Bruker SAINT [9]'
_computing_molecular_graphics    'Bruker SHELXTL [8]'
_computing_publication_material  'Bruker SHELXTL [8]'
_computing_structure_refinement  'SHELXL-2013 [10]'
_computing_structure_solution    'SHELXS-2013 [10]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6124
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0083(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2287
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0499P)²+0.6610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                1932
_reflns_number_total             2287
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2018-0234_suppl.cif
_cod_data_source_block           xb9485_0m
_cod_original_cell_volume        2571.8(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8105792
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_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
N1 N 0.18263(4) 1.0440(2) 0.63917(7) 0.0494(3) Uani 1 1 d . . .
N2 N 0.07714(3) 1.01814(19) 0.62604(7) 0.0458(3) Uani 1 1 d . . .
H2 H 0.0911 1.1309 0.6012 0.055 Uiso 1 1 calc R . .
N3 N 0.02846(3) 1.00685(18) 0.62401(6) 0.0428(3) Uani 1 1 d . . .
N4 N 0.00952(3) 1.17546(18) 0.58451(6) 0.0443(3) Uani 1 1 d . . .
O1 O 0.22620(3) 1.0524(2) 0.65413(8) 0.0812(4) Uani 1 1 d . . .
O2 O 0.16171(3) 1.18838(17) 0.59357(6) 0.0582(3) Uani 1 1 d . . .
O3 O -0.19050(3) 1.19616(17) 0.54348(6) 0.0568(3) Uani 1 1 d . . .
C1 C 0.15512(4) 0.8591(2) 0.67634(7) 0.0428(3) Uani 1 1 d . . .
C2 C 0.18143(5) 0.6914(3) 0.72205(8) 0.0516(4) Uani 1 1 d . . .
H2A H 0.2149 0.7018 0.7272 0.062 Uiso 1 1 calc R . .
C3 C 0.15860(5) 0.5121(3) 0.75937(9) 0.0576(4) Uani 1 1 d . . .
H3 H 0.1762 0.4017 0.7908 0.069 Uiso 1 1 calc R . .
C4 C 0.10865(5) 0.4960(3) 0.74991(9) 0.0555(4) Uani 1 1 d . . .
H4 H 0.0929 0.3721 0.7745 0.067 Uiso 1 1 calc R . .
C5 C 0.08217(5) 0.6596(2) 0.70496(8) 0.0493(3) Uani 1 1 d . . .
H5 H 0.0488 0.6438 0.6992 0.059 Uiso 1 1 calc R . .
C6 C 0.10437(4) 0.8501(2) 0.66757(7) 0.0403(3) Uani 1 1 d . . .
C7 C -0.04178(4) 1.1681(2) 0.57883(7) 0.0386(3) Uani 1 1 d . . .
C8 C -0.06500(4) 1.3558(2) 0.53913(8) 0.0447(3) Uani 1 1 d . . .
H8 H -0.0470 1.4797 0.5193 0.054 Uiso 1 1 calc R . .
C9 C -0.11460(4) 1.3604(2) 0.52877(8) 0.0462(3) Uani 1 1 d . . .
H9 H -0.1299 1.4877 0.5022 0.055 Uiso 1 1 calc R . .
C10 C -0.14181(4) 1.1770(2) 0.55763(8) 0.0413(3) Uani 1 1 d . . .
C11 C -0.11889(4) 0.9895(2) 0.59774(8) 0.0456(3) Uani 1 1 d . . .
H11 H -0.1370 0.8664 0.6179 0.055 Uiso 1 1 calc R . .
C12 C -0.06924(4) 0.9850(2) 0.60792(8) 0.0447(3) Uani 1 1 d . . .
H12 H -0.0540 0.8578 0.6346 0.054 Uiso 1 1 calc R . .
C13 C -0.22012(5) 1.0107(3) 0.57198(11) 0.0624(4) Uani 1 1 d . . .
H13A H -0.2111 0.8634 0.5480 0.094 Uiso 1 1 calc R . .
H13B H -0.2534 1.0442 0.5568 0.094 Uiso 1 1 calc R . .
H13C H -0.2158 0.9999 0.6302 0.094 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 N1 O2 121.57(12) . .
O1 N1 C1 118.88(11) . .
O2 N1 C1 119.55(10) . .
N3 N2 C6 120.06(10) . .
N3 N2 H2 120.0 . .
C6 N2 H2 120.0 . .
N4 N3 N2 111.46(10) . .
N3 N4 C7 113.60(10) . .
C10 O3 C13 118.05(10) . .
C2 C1 C6 121.40(12) . .
C2 C1 N1 116.51(11) . .
C6 C1 N1 122.09(11) . .
C3 C2 C1 120.53(13) . .
C3 C2 H2A 119.7 . .
C1 C2 H2A 119.7 . .
C2 C3 C4 119.13(12) . .
C2 C3 H3 120.4 . .
C4 C3 H3 120.4 . .
C5 C4 C3 121.09(13) . .
C5 C4 H4 119.5 . .
C3 C4 H4 119.5 . .
C4 C5 C6 121.30(12) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
N2 C6 C5 120.48(11) . .
N2 C6 C1 123.01(11) . .
C5 C6 C1 116.51(11) . .
C8 C7 C12 118.97(11) . .
C8 C7 N4 116.43(10) . .
C12 C7 N4 124.58(10) . .
C9 C8 C7 120.45(11) . .
C9 C8 H8 119.8 . .
C7 C8 H8 119.8 . .
C8 C9 C10 120.36(11) . .
C8 C9 H9 119.8 . .
C10 C9 H9 119.8 . .
O3 C10 C11 124.50(11) . .
O3 C10 C9 115.99(10) . .
C11 C10 C9 119.51(11) . .
C12 C11 C10 120.04(11) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C11 C12 C7 120.66(11) . .
C11 C12 H12 119.7 . .
C7 C12 H12 119.7 . .
O3 C13 H13A 109.5 . .
O3 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
O3 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 O1 1.2205(13) .
N1 O2 1.2297(14) .
N1 C1 1.4497(17) .
N2 N3 1.3508(14) .
N2 C6 1.3699(15) .
N2 H2 0.8600 .
N3 N4 1.2509(14) .
N4 C7 1.4216(15) .
O3 C10 1.3615(14) .
O3 C13 1.4275(17) .
C1 C2 1.3895(18) .
C1 C6 1.4079(17) .
C2 C3 1.360(2) .
C2 H2A 0.9300 .
C3 C4 1.389(2) .
C3 H3 0.9300 .
C4 C5 1.3693(19) .
C4 H4 0.9300 .
C5 C6 1.4001(18) .
C5 H5 0.9300 .
C7 C8 1.3837(16) .
C7 C12 1.3867(17) .
C8 C9 1.3771(17) .
C8 H8 0.9300 .
C9 C10 1.3826(17) .
C9 H9 0.9300 .
C10 C11 1.3824(17) .
C11 C12 1.3781(17) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
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
C6 N2 N3 N4 179.08(10) . . . .
N2 N3 N4 C7 178.48(9) . . . .
O1 N1 C1 C2 -4.89(18) . . . .
O2 N1 C1 C2 175.17(11) . . . .
O1 N1 C1 C6 174.48(12) . . . .
O2 N1 C1 C6 -5.46(18) . . . .
C6 C1 C2 C3 0.4(2) . . . .
N1 C1 C2 C3 179.75(12) . . . .
C1 C2 C3 C4 1.3(2) . . . .
C2 C3 C4 C5 -1.1(2) . . . .
C3 C4 C5 C6 -0.6(2) . . . .
N3 N2 C6 C5 3.00(17) . . . .
N3 N2 C6 C1 -176.02(11) . . . .
C4 C5 C6 N2 -176.92(12) . . . .
C4 C5 C6 C1 2.16(18) . . . .
C2 C1 C6 N2 177.01(11) . . . .
N1 C1 C6 N2 -2.33(18) . . . .
C2 C1 C6 C5 -2.04(18) . . . .
N1 C1 C6 C5 178.62(11) . . . .
N3 N4 C7 C8 177.06(11) . . . .
N3 N4 C7 C12 -4.88(17) . . . .
C12 C7 C8 C9 0.04(19) . . . .
N4 C7 C8 C9 178.21(11) . . . .
C7 C8 C9 C10 -0.28(19) . . . .
C13 O3 C10 C11 0.10(19) . . . .
C13 O3 C10 C9 179.86(12) . . . .
C8 C9 C10 O3 -179.15(11) . . . .
C8 C9 C10 C11 0.63(19) . . . .
O3 C10 C11 C12 179.01(12) . . . .
C9 C10 C11 C12 -0.74(19) . . . .
C10 C11 C12 C7 0.5(2) . . . .
C8 C7 C12 C11 -0.16(19) . . . .
N4 C7 C12 C11 -178.17(11) . . . .
