#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/49/2014940.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_2014940
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          'C13 H12 F N3'
_chemical_formula_moiety         'C13 H12 F N3'
_chemical_formula_sum            'C13 H12 F N3'
_chemical_formula_weight         229.26
_chemical_name_systematic
;
1-(4-fluorophenyl)-3-(4-methylphenyl)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                 92.512(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.683(3)
_cell_length_b                   4.7712(6)
_cell_length_c                   17.742(4)
_cell_measurement_reflns_used    3288
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      1.84
_cell_volume                     1157.2(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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0812
_diffrn_reflns_av_sigmaI/netI    0.1028
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_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            6441
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.850
_refine_ls_R_factor_all          0.1532
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0316P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1103
_reflns_number_gt                757
_reflns_number_total             2019
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ta1464.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2014940
_cod_database_fobs_code          2014940
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
F1 0.59689(18) -0.2842(5) 0.41441(11) 0.1179(9) Uani d . 1 . . F
N1 0.7588(2) 0.3437(6) 0.65048(13) 0.0690(8) Uani d . 1 . . N
N2 0.8287(2) 0.5281(6) 0.64092(15) 0.0612(7) Uani d . 1 . . N
N3 0.8525(2) 0.6608(6) 0.70168(13) 0.0646(8) Uani d . 1 . . N
C1 0.7201(3) 0.1830(7) 0.59027(15) 0.0605(9) Uani d . 1 . . C
C2 0.6487(3) -0.0110(8) 0.6024(2) 0.0704(11) Uani d . 1 . . C
C3 0.6081(3) -0.1655(8) 0.5441(2) 0.0800(11) Uani d . 1 . . C
C4 0.6405(3) -0.1262(8) 0.47375(18) 0.0713(10) Uani d . 1 . . C
C5 0.7111(3) 0.0606(9) 0.4589(2) 0.0764(11) Uani d . 1 . . C
C6 0.7531(3) 0.2209(8) 0.51692(18) 0.0740(11) Uani d . 1 . . C
C7 0.9297(2) 0.8534(7) 0.69146(15) 0.0610(9) Uani d . 1 . . C
C8 0.9712(3) 0.9756(8) 0.7551(2) 0.0731(11) Uani d . 1 . . C
C9 1.0464(3) 1.1635(9) 0.7525(2) 0.0799(11) Uani d . 1 . . C
C10 1.0837(2) 1.2405(7) 0.6842(2) 0.0705(10) Uani d . 1 . . C
C11 1.0410(3) 1.1238(9) 0.6199(2) 0.0773(11) Uani d . 1 . . C
C12 0.9664(3) 0.9370(9) 0.62253(19) 0.0728(11) Uani d . 1 . . C
C13 1.1642(2) 1.4475(7) 0.68079(18) 0.0750(11) Uani d . 1 . . C
H1 0.7365 0.3214 0.6946 0.083 Uiso calc R 1 . . H
H2 0.635(3) -0.038(8) 0.651(2) 0.116(14) Uiso d . 1 . . H
H3 0.5591 -0.2954 0.5526 0.096 Uiso calc R 1 . . H
H5 0.728(3) 0.097(8) 0.4075(19) 0.115(13) Uiso d . 1 . . H
H6 0.805(2) 0.352(6) 0.5094(15) 0.063(9) Uiso d . 1 . . H
H8 0.956(2) 0.915(8) 0.8017(19) 0.104(13) Uiso d . 1 . . H
H9 1.080(2) 1.238(6) 0.7958(15) 0.067(10) Uiso d . 1 . . H
H11 1.061(2) 1.189(6) 0.5717(16) 0.086(11) Uiso d . 1 . . H
H12 0.936(2) 0.852(6) 0.5843(15) 0.069(11) Uiso d . 1 . . H
H13A 1.1614 1.5744 0.7226 0.112 Uiso calc R 1 . . H
H13B 1.1574 1.5509 0.6344 0.112 Uiso calc R 1 . . H
H13C 1.2259 1.3513 0.6831 0.112 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'
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 121.4(3)
N2 N1 H1 119.3
C1 N1 H1 119.3
N3 N2 N1 112.4(3)
N2 N3 C7 112.1(2)
C2 C1 N1 119.9(3)
C2 C1 C6 119.5(3)
N1 C1 C6 120.6(3)
C3 C2 C1 120.9(4)
C3 C2 H2 124(2)
C1 C2 H2 115(2)
C4 C3 C2 118.9(4)
C4 C3 H3 120.5
C2 C3 H3 120.5
C5 C4 C3 122.5(4)
C5 C4 F1 119.4(3)
C3 C4 F1 118.1(4)
C4 C5 C6 119.7(4)
C4 C5 H5 121(2)
C6 C5 H5 119(2)
C5 C6 C1 118.5(4)
C5 C6 H6 122.8(17)
C1 C6 H6 118.7(17)
C8 C7 C12 116.5(4)
C8 C7 N3 117.0(3)
C12 C7 N3 126.5(3)
C9 C8 C7 122.4(4)
C9 C8 H8 116(2)
C7 C8 H8 121(2)
C8 C9 C10 120.7(4)
C8 C9 H9 124.1(18)
C10 C9 H9 115.0(18)
C11 C10 C9 117.3(4)
C11 C10 C13 121.7(4)
C9 C10 C13 121.0(4)
C12 C11 C10 122.0(4)
C12 C11 H11 119.2(18)
C10 C11 H11 118.6(18)
C11 C12 C7 121.0(4)
C11 C12 H12 127.5(19)
C7 C12 H12 111.4(19)
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 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
F1 C4 . 1.406(4) ?
N1 N2 . 1.316(3) ?
N1 C1 . 1.400(4) ?
N1 H1 . 0.8600 ?
N2 N3 . 1.280(3) ?
N3 C7 . 1.417(4) ?
C1 C2 . 1.370(4) ?
C1 C6 . 1.408(4) ?
C2 C3 . 1.369(4) ?
C2 H2 . 0.90(4) ?
C3 C4 . 1.355(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.350(5) ?
C5 C6 . 1.387(5) ?
C5 H5 . 0.97(3) ?
C6 H6 . 0.96(3) ?
C7 C8 . 1.372(4) ?
C7 C12 . 1.400(4) ?
C8 C9 . 1.367(5) ?
C8 H8 . 0.91(3) ?
C9 C10 . 1.385(5) ?
C9 H9 . 0.95(3) ?
C10 C11 . 1.376(5) ?
C10 C13 . 1.483(4) ?
C11 C12 . 1.357(5) ?
C11 H11 . 0.96(3) ?
C12 H12 . 0.88(3) ?
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
C1 N1 N2 N3 177.9(3)
N1 N2 N3 C7 178.3(3)
N2 N1 C1 C2 178.8(3)
N2 N1 C1 C6 -2.0(4)
N1 C1 C2 C3 178.4(3)
C6 C1 C2 C3 -0.9(5)
C1 C2 C3 C4 0.7(5)
C2 C3 C4 C5 -0.2(5)
C2 C3 C4 F1 -179.1(3)
C3 C4 C5 C6 -0.1(6)
F1 C4 C5 C6 178.8(3)
C4 C5 C6 C1 0.0(5)
C2 C1 C6 C5 0.5(5)
N1 C1 C6 C5 -178.7(3)
N2 N3 C7 C8 -170.3(3)
N2 N3 C7 C12 11.4(4)
C12 C7 C8 C9 -1.9(5)
N3 C7 C8 C9 179.7(3)
C7 C8 C9 C10 0.6(6)
C8 C9 C10 C11 0.9(5)
C8 C9 C10 C13 179.0(3)
C9 C10 C11 C12 -1.0(5)
C13 C10 C11 C12 -179.1(3)
C10 C11 C12 C7 -0.3(6)
C8 C7 C12 C11 1.7(5)
N3 C7 C12 C11 -179.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133854
