#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/05/2230574.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_2230574
loop_
_publ_author_name
'Rofouei, Mohammad Kazem'
'Ghalami, Zahra'
'Attar Gharamaleki, Jafar'
'Bruno, Giuseppe'
'Amiri Rudbari, Hadi'
_publ_section_title
;
 4-[(4-Chlorophenyl)diazenyl]-3-methoxyaniline
;
_journal_coeditor_code           BH2358
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1852
_journal_paper_doi               10.1107/S160053681102472X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H12 Cl N3 O'
_chemical_formula_moiety         'C13 H12 Cl N3 O'
_chemical_formula_sum            'C13 H12 Cl N3 O'
_chemical_formula_weight         261.71
_chemical_melting_point          464
_chemical_name_systematic
;
4-[(4-Chlorophenyl)diazenyl]-3-methoxyaniline
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00000
_cell_angle_beta                 107.650(10)
_cell_angle_gamma                90.00000
_cell_formula_units_Z            8
_cell_length_a                   15.398(2)
_cell_length_b                   12.132(2)
_cell_length_c                   14.276(2)
_cell_measurement_reflns_used    9801
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.78
_cell_measurement_theta_min      2.39
_cell_volume                     2541.3(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2005)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0084
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            42735
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.388
_refine_ls_extinction_coef       0.0021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0388
_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)+(0.0630P)²+1.2073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1180
_reflns_number_gt                2481
_reflns_number_total             2778
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2358.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2230574
_cod_database_fobs_code          2230574
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.38256(4) 0.12838(5) 0.25280(3) 0.0899(2) Uani d . 1 1 . .
N N2 0.61207(7) 0.40377(9) 0.64610(8) 0.0428(3) Uani d . 1 1 . .
O O 0.72867(7) 0.56731(8) 0.66289(7) 0.0538(3) Uani d . 1 1 . .
N N3 0.56583(8) 0.31792(9) 0.64438(8) 0.0450(3) Uani d . 1 1 . .
C C8 0.70965(9) 0.53992(11) 0.74685(9) 0.0425(3) Uani d . 1 1 . .
C C1 0.52338(9) 0.27653(11) 0.54826(9) 0.0435(3) Uani d . 1 1 . .
C C7 0.64918(9) 0.45106(10) 0.73903(9) 0.0401(3) Uani d . 1 1 . .
C C9 0.74743(10) 0.59254(12) 0.83601(10) 0.0478(3) Uani d . 1 1 . .
H H9 0.7869 0.6517 0.8403 0.057 Uiso calc R 1 1 . .
C C11 0.66611(10) 0.46804(12) 0.91223(10) 0.0485(3) Uani d . 1 1 . .
H H11 0.6520 0.4436 0.9676 0.058 Uiso calc R 1 1 . .
C C10 0.72618(10) 0.55670(12) 0.91959(10) 0.0484(3) Uani d . 1 1 . .
C C12 0.62817(9) 0.41745(11) 0.82355(10) 0.0437(3) Uani d . 1 1 . .
H H12 0.5876 0.3595 0.8193 0.052 Uiso calc R 1 1 . .
C C6 0.51547(11) 0.33586(13) 0.46265(11) 0.0543(4) Uani d . 1 1 . .
H H6 0.5398 0.4065 0.4665 0.065 Uiso calc R 1 1 . .
N N1 0.76334(13) 0.60746(16) 1.00811(11) 0.0723(5) Uani d . 1 1 . .
C C2 0.48455(12) 0.17279(13) 0.54185(12) 0.0590(4) Uani d . 1 1 . .
H H2 0.4879 0.1338 0.5989 0.071 Uiso calc R 1 1 . .
C C3 0.44078(12) 0.12672(14) 0.45107(13) 0.0658(4) Uani d . 1 1 . .
H H3 0.4150 0.0569 0.4467 0.079 Uiso calc R 1 1 . .
C C4 0.43604(11) 0.18557(15) 0.36754(12) 0.0589(4) Uani d . 1 1 . .
C C5 0.47166(12) 0.29024(15) 0.37226(11) 0.0619(4) Uani d . 1 1 . .
H H5 0.4662 0.3298 0.3150 0.074 Uiso calc R 1 1 . .
C C13 0.78626(14) 0.65978(16) 0.66487(13) 0.0711(5) Uani d . 1 1 . .
H H13A 0.7942 0.6693 0.6012 0.107 Uiso calc R 1 1 . .
H H13B 0.8445 0.6475 0.7128 0.107 Uiso calc R 1 1 . .
H H13C 0.7589 0.7248 0.6820 0.107 Uiso calc R 1 1 . .
H H1A 0.7476(16) 0.5869(19) 1.0576(17) 0.085(7) Uiso d . 1 1 . .
H H1B 0.8002(15) 0.6559(18) 1.0126(16) 0.075(6) Uiso d . 1 1 . .
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 N2 C7 . . 115.10(11) ?
C8 O C13 . . 118.32(11) ?
N2 N3 C1 . . 113.79(11) ?
O C8 C9 . . 123.74(12) ?
O C8 C7 . . 115.59(11) ?
C9 C8 C7 . . 120.65(12) ?
C2 C1 C6 . . 119.42(13) ?
C2 C1 N3 . . 116.62(13) ?
C6 C1 N3 . . 123.89(12) ?
N2 C7 C12 . . 124.25(12) ?
N2 C7 C8 . . 117.38(11) ?
C12 C7 C8 . . 118.34(11) ?
C8 C9 C10 . . 119.94(13) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C12 C11 C10 . . 120.03(12) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
N1 C10 C9 . . 120.56(15) ?
N1 C10 C11 . . 119.81(14) ?
C9 C10 C11 . . 119.63(12) ?
C11 C12 C7 . . 121.39(13) ?
C11 C12 H12 . . 119.3 ?
C7 C12 H12 . . 119.3 ?
C5 C6 C1 . . 120.16(14) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
C10 N1 H1B . . 119.4(16) ?
C10 N1 H1A . . 119.5(16) ?
H1B N1 H1A . . 121(2) ?
C3 C2 C1 . . 120.45(15) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C4 C3 C2 . . 119.06(15) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
C3 C4 C5 . . 121.45(14) ?
C3 C4 Cl . . 119.73(13) ?
C5 C4 Cl . . 118.81(13) ?
C4 C5 C6 . . 119.40(15) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
O C13 H13A . . 109.5 ?
O C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C4 . 1.7391(16) ?
N2 N3 . 1.2578(16) ?
N2 C7 . 1.3985(16) ?
O C8 . 1.3586(16) ?
O C13 . 1.4250(18) ?
N3 C1 . 1.4206(17) ?
C8 C9 . 1.3846(18) ?
C8 C7 . 1.4065(18) ?
C1 C2 . 1.384(2) ?
C1 C6 . 1.392(2) ?
C7 C12 . 1.4014(18) ?
C9 C10 . 1.3987(19) ?
C9 H9 . 0.9300 ?
C11 C12 . 1.3683(19) ?
C11 C10 . 1.402(2) ?
C11 H11 . 0.9300 ?
C10 N1 . 1.3657(19) ?
C12 H12 . 0.9300 ?
C6 C5 . 1.378(2) ?
C6 H6 . 0.9300 ?
N1 H1B . 0.81(2) ?
N1 H1A . 0.85(2) ?
C2 C3 . 1.384(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.373(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.377(2) ?
C5 H5 . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
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
_geom_hbond_publ_flag
N1 H1A O 6_566 0.85(2) 2.47(2) 3.222(2) 147(2) yes
C12 H12 N3 2_656 0.93 2.62 3.379(2) 140 yes
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N2 N3 C1 . . . . 175.50(10) ?
C13 O C8 C9 . . . . -4.1(2) ?
C13 O C8 C7 . . . . 177.23(14) ?
N2 N3 C1 C2 . . . . 169.37(13) ?
N2 N3 C1 C6 . . . . -13.7(2) ?
N3 N2 C7 C12 . . . . -8.56(19) ?
N3 N2 C7 C8 . . . . 173.14(11) ?
O C8 C7 N2 . . . . -2.78(18) ?
C9 C8 C7 N2 . . . . 178.49(12) ?
O C8 C7 C12 . . . . 178.82(12) ?
C9 C8 C7 C12 . . . . 0.1(2) ?
O C8 C9 C10 . . . . -178.02(13) ?
C7 C8 C9 C10 . . . . 0.6(2) ?
C8 C9 C10 N1 . . . . 179.64(15) ?
C8 C9 C10 C11 . . . . -0.5(2) ?
C12 C11 C10 N1 . . . . 179.51(15) ?
C12 C11 C10 C9 . . . . -0.4(2) ?
C10 C11 C12 C7 . . . . 1.1(2) ?
N2 C7 C12 C11 . . . . -179.24(12) ?
C8 C7 C12 C11 . . . . -1.0(2) ?
C2 C1 C6 C5 . . . . -1.9(2) ?
N3 C1 C6 C5 . . . . -178.75(14) ?
C6 C1 C2 C3 . . . . 2.1(2) ?
N3 C1 C2 C3 . . . . 179.20(15) ?
C1 C2 C3 C4 . . . . -0.3(3) ?
C2 C3 C4 C5 . . . . -1.7(3) ?
C2 C3 C4 Cl . . . . 179.22(14) ?
C3 C4 C5 C6 . . . . 2.0(3) ?
Cl C4 C5 C6 . . . . -178.99(14) ?
C1 C6 C5 C4 . . . . -0.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 15261908
