<i>syn</i> and <i>anti</i> conformations in 2-hydroxy-5-[(<i>E</i>)-(4-nitrophenyl)diazenyl]benzoic acid and two related salts
Yatsenko, Alexandr V.; Paseshnichenko, Ksenia A.; Acta Crystallographica Section C 70 (2014) 493–497; doi:10.1107/S2053229614007827

data_2019507
_publ_section_title
;
 <i>syn</i> and <i>anti</i> conformations in
 2-hydroxy-5-[(<i>E</i>)-(4-nitrophenyl)diazenyl]benzoic acid and two
 related salts
;
_journal_coeditor_code           YF3059
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              493
_journal_page_last               497
_journal_paper_doi               10.1107/S2053229614007827
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C13 H9 N3 O5'
_chemical_formula_moiety         'C13 H9 N3 O5'
_chemical_formula_sum            'C13 H9 N3 O5'
_chemical_formula_weight         287.23
_chemical_melting_point          530
_chemical_name_common            'C.I. Mordant Orange 1'
_chemical_name_systematic
;
2-Hydroxy-5-[(<i>E</i>)-(4-nitrophenyl)diazenyl]benzoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.991(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9319(5)
_cell_length_b                   11.6649(14)
_cell_length_c                   21.619(2)
_cell_measurement_reflns_used    2234
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.34
_cell_measurement_theta_min      3.78
_cell_volume                     1239.0(2)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2012)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2012)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2012)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14169
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.00
_diffrn_reflns_theta_min         4.11
_exptl_absorpt_coefficient_mu    1.037
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            red--orange
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             592.0
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.177
_refine_ls_extinction_coef       0.0143(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2334
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0832P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                1804
_reflns_number_total             2334
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            yf3059sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2019506--2019508.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2019507
_cod_database_fobs_code          2019507