1,3-Bis(4-methylphenyl)triazene, 1-(4-chlorophenyl)-3-(4-fluorophenyl)triazene and 1-(4-fluorophenyl)-3-(4-methylphenyl)triazene
Karadayı, Nevzat; C̨akmak, S̨ükriye; Odabas̨oğlu, Mustafa; Büyükgüngör, Orhan; Acta Crystallographica Section C 61 (2005) o303–o305; doi:10.1107/S0108270105004373

data_2014939
_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       '\w 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/[\s^2^(Fo^2^)+(0.1152P)^2^] where P=(Fo^2^+2Fc^2^)/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>2\s(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