#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/49/2014939.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_2014939
loop_
_publ_author_name
'Karadayı, Nevzat'
'C̨akmak, S̨ükriye'
'Odabas̨oğlu, Mustafa '
'Büyükgüngör, Orhan'
_publ_section_title
;
 1,3-Bis(4-methylphenyl)triazene,
 1-(4-chlorophenyl)-3-(4-fluorophenyl)triazene and
 1-(4-fluorophenyl)-3-(4-methylphenyl)triazene
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o303
_journal_page_last               o305
_journal_paper_doi               10.1107/S0108270105004373
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H9 Cl F N3'
_chemical_formula_moiety         'C12 H9 Cl F N3'
_chemical_formula_sum            'C12 H9 Cl F N3'
_chemical_formula_weight         249.67
_chemical_name_systematic
;
1-(4-chlorophenyl)-3-(4-fluorophenyl)triazene
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.298(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.500(3)
_cell_length_b                   4.7385(5)
_cell_length_c                   17.848(3)
_cell_measurement_reflns_used    4244
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.42
_cell_measurement_theta_min      1.78
_cell_volume                     1225.3(4)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 1997)
;
_computing_publication_material
;
WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8654
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.8858
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe&Cie, 2002)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.443
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2157
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.293
_refine_ls_R_factor_all          0.1704
_refine_ls_R_factor_gt           0.0867
_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)+(0.1152P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2182
_refine_ls_wR_factor_ref         0.2534
_reflns_number_gt                978
_reflns_number_total             2157
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ta1464.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2014939
_cod_database_fobs_code          2014939
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.59926(18) -0.3008(6) 0.40352(15) 0.1056(11) Uani d . 1 . . Cl
F1 1.1636(3) 1.4616(11) 0.6800(3) 0.1030(18) Uani d D 1 . . F
N1 0.7594(4) 0.3764(14) 0.6514(3) 0.0663(17) Uani d . 1 . . N
N2 0.8269(4) 0.5565(12) 0.6397(4) 0.0584(16) Uani d . 1 . . N
N3 0.8480(4) 0.7023(13) 0.7008(3) 0.0586(15) Uani d . 1 . . N
C1 0.7251(5) 0.2108(14) 0.5920(4) 0.0515(17) Uani d . 1 . . C
C2 0.6540(5) 0.0309(16) 0.6034(4) 0.066(2) Uani d . 1 . . C
C3 0.6152(5) -0.1239(17) 0.5473(4) 0.067(2) Uani d . 1 . . C
C4 0.6490(5) -0.1087(15) 0.4770(4) 0.0573(18) Uani d . 1 . . C
C5 0.7222(5) 0.0627(16) 0.4628(4) 0.066(2) Uani d . 1 . . C
C6 0.7609(5) 0.2270(15) 0.5195(4) 0.066(2) Uani d . 1 . . C
C7 0.9237(4) 0.8901(14) 0.6902(4) 0.0484(16) Uani d . 1 . . C
C8 0.9579(5) 1.0271(16) 0.7524(4) 0.063(2) Uani d . 1 . . C
C9 1.0311(5) 1.2078(16) 0.7500(4) 0.065(2) Uani d . 1 . . C
C10 1.0765(5) 1.2662(14) 0.6839(4) 0.0568(18) Uani d D 1 . . C
C11 1.0376(6) 1.1284(17) 0.6210(4) 0.071(2) Uani d . 1 . . C
C12 0.9648(5) 0.9467(16) 0.6230(4) 0.062(2) Uani d . 1 . . C
H1 0.7369 0.3615 0.6951 0.080 Uiso calc R 1 . . H
H2 0.6316 0.0144 0.6513 0.080 Uiso calc R 1 . . H
H3 0.5655 -0.2412 0.5564 0.080 Uiso calc R 1 . . H
H5 0.7457 0.0684 0.4151 0.079 Uiso calc R 1 . . H
H6 0.8099 0.3469 0.5103 0.079 Uiso calc R 1 . . H
H8 0.9305 0.9966 0.7979 0.076 Uiso calc R 1 . . H
H9 1.0517 1.2958 0.7942 0.078 Uiso calc R 1 . . H
H11 1.0630 1.1629 0.5749 0.085 Uiso calc R 1 . . H
H12 0.9427 0.8603 0.5790 0.074 Uiso calc R 1 . . H
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'
Cl Cl 0.1484 0.1585 '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'
F F 0.0171 0.0103 '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
N2 N1 C1 119.2(6)
N2 N1 H1 120.4
C1 N1 H1 120.4
N3 N2 N1 110.9(6)
N2 N3 C7 111.8(5)
C2 C1 N1 119.3(7)
C2 C1 C6 118.6(7)
N1 C1 C6 122.1(7)
C3 C2 C1 121.9(8)
C3 C2 H2 119.1
C1 C2 H2 119.1
C2 C3 C4 119.9(8)
C2 C3 H3 120.0
C4 C3 H3 120.0
C3 C4 C5 120.7(7)
C3 C4 Cl1 121.0(6)
C5 C4 Cl1 118.3(6)
C4 C5 C6 119.6(7)
C4 C5 H5 120.2
C6 C5 H5 120.2
C5 C6 C1 119.2(7)
C5 C6 H6 120.4
C1 C6 H6 120.4
C8 C7 C12 117.2(7)
C8 C7 N3 116.5(6)
C12 C7 N3 126.4(6)
C7 C8 C9 122.2(7)
C7 C8 H8 118.9
C9 C8 H8 118.9
C8 C9 C10 122.8(7)
C8 C9 H9 118.6
C10 C9 H9 118.6
C11 C10 C9 113.3(7)
C11 C10 F1 122.7(6)
C9 C10 F1 124.0(6)
C12 C11 C10 124.3(7)
C12 C11 H11 117.9
C10 C11 H11 117.9
C11 C12 C7 120.2(7)
C11 C12 H12 119.9
C7 C12 H12 119.9
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
F1 C10 . 1.569(8) ?
N1 N2 . 1.321(7) ?
N1 C1 . 1.394(8) ?
N1 H1 . 0.8600 ?
N2 N3 . 1.317(8) ?
N3 C7 . 1.431(9) ?
Cl1 C4 . 1.731(7) ?
C1 C2 . 1.359(10) ?
C1 C6 . 1.415(10) ?
C2 C3 . 1.345(10) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.367(10) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.369(10) ?
C5 C6 . 1.379(10) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.361(9) ?
C7 C12 . 1.388(9) ?
C8 C9 . 1.366(10) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.403(10) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.397(10) ?
C11 C12 . 1.364(10) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
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
C1 N1 N2 N3 177.5(5)
N1 N2 N3 C7 177.5(5)
N2 N1 C1 C2 -178.3(6)
N2 N1 C1 C6 0.7(9)
N1 C1 C2 C3 176.8(7)
C6 C1 C2 C3 -2.2(11)
C1 C2 C3 C4 1.9(12)
C2 C3 C4 C5 0.1(11)
C2 C3 C4 Cl1 -178.9(6)
C3 C4 C5 C6 -1.6(11)
Cl1 C4 C5 C6 177.4(5)
C4 C5 C6 C1 1.2(11)
C2 C1 C6 C5 0.7(10)
N1 C1 C6 C5 -178.3(6)
N2 N3 C7 C8 -172.7(6)
N2 N3 C7 C12 7.7(9)
C12 C7 C8 C9 -1.6(10)
N3 C7 C8 C9 178.7(6)
C7 C8 C9 C10 0.0(12)
C8 C9 C10 C11 1.8(11)
C8 C9 C10 F1 -177.0(6)
C9 C10 C11 C12 -2.2(11)
F1 C10 C11 C12 176.7(6)
C10 C11 C12 C7 0.7(12)
C8 C7 C12 C11 1.3(10)
N3 C7 C12 C11 -179.1(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133853
