Molecular cocrystals of 5-(4-bromophenyl)-1,3,4-thiadiazol-2-amine: hydrogen bonding in the structures of the 1:1 adduct with 2-(naphthalen-2-yloxy)acetic acid and the salt with 3,5-dinitrobenzoic acid
Smith, Graham; Lynch, Daniel E.; Acta Crystallographica Section C 69 (2013) 1034–1038; doi:10.1107/S0108270113019665

data_2019126
_publ_section_title
;
 Molecular cocrystals of 5-(4-bromophenyl)-1,3,4-thiadiazol-2-amine:
 hydrogen bonding in the structures of the 1:1 adduct with
 2-(naphthalen-2-yloxy)acetic acid and the salt with 3,5-dinitrobenzoic
 acid
;
_journal_coeditor_code           FG3301
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1034
_journal_page_last               1038
_journal_paper_doi               10.1107/S0108270113019665
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C8 H6 Br N3 S , C12 H10 O3'
_chemical_formula_moiety         'C8 H6 Br N3 S, C12 H10 O3'
_chemical_formula_sum            'C20 H16 Br N3 O3 S'
_chemical_formula_weight         458.33
_chemical_name_systematic
;
5-(4-Bromophenyl)-1,3,4-thiadiazol-2-amine--2-(naphthalen-2-yloxy)acetic acid
(1/1)
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   41.357(2)
_cell_length_b                   3.9369(3)
_cell_length_c                   11.4761(5)
_cell_measurement_reflns_used    1229
_cell_measurement_temperature    200.0(10)
_cell_measurement_theta_max      28.79
_cell_measurement_theta_min      3.44
_cell_volume                     1868.52(19)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200.0(10)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Gemini-S CCD area-detector'
_diffrn_measurement_method       \w
_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  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5208
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.339
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.398
_refine_ls_abs_structure_details 'Flack (1983), with 1386 Friedel pairs'
_refine_ls_abs_structure_Flack   0.001(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3309
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0169P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                2842
_reflns_number_total             3309
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3301.cif
_cod_data_source_block           I
_cod_original_cell_volume        1868.53(19)
_cod_database_code               2019126
_cod_database_fobs_code          2019126