4-Chloro-2-[(4-chlorobenzylidene)amino]phenol
Efil, Kürşat; Şen, Fatih; Bekdemir, Yunus; Büyükgüngör, Orhan; Acta Crystallographica Section E 68 (2012) o1696–; doi:10.1107/S1600536812019770

data_2235337
_publ_section_title
;
 4-Chloro-2-[(4-chlorobenzylidene)amino]phenol
;
_journal_coeditor_code           ZS2205
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1696
_journal_paper_doi               10.1107/S1600536812019770
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H9 Cl2 N O'
_chemical_formula_moiety         'C13 H9 Cl2 N O'
_chemical_formula_sum            'C13 H9 Cl2 N O'
_chemical_formula_weight         266.11
_chemical_melting_point_gt       396
_chemical_melting_point_lt       398
_chemical_name_common
<i>N</i>-(4-chlorobenzylidene)-2-hydroxy-5-chloroaniline
_chemical_name_systematic
;
4-Chloro-2-[(4-chlorobenzylidene)amino]phenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6615(2)
_cell_length_b                   10.5375(5)
_cell_length_c                   25.2153(15)
_cell_measurement_reflns_used    16508
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      1.61
_cell_volume                     1238.59(11)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS 2 CCD'
_diffrn_measurement_method       'rotation method'
_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  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            2562
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  0.8819
_exptl_absorpt_correction_T_min  0.8146
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.235
_refine_ls_abs_structure_details 'Flack (1983), 1024 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0496P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                1910
_reflns_number_total             2562
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            zs2205.cif
_cod_data_source_block           I
_cod_database_code               2235337
_cod_database_fobs_code          2235337