A comparative experimental and theoretical investigation of hydrogen-bond, halogen-bond and π–π interactions in the solid-state supramolecular assembly of 2- and 4-formylphenyl arylsulfonates
Andleeb, Hina; Khan, Imtiaz; Bauzá, Antonio; Tahir, Muhammad Nawaz; Simpson, Jim; Hameed, Shahid; Frontera, Antonio; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618008355

data_2021159
_publ_section_title
;
 A comparative experimental and theoretical investigation of
 hydrogen-bond, halogen-bond and \p--\p interactions in the solid-state
 supramolecular assembly of 2- and 4-formylphenyl arylsulfonates
;
_journal_coeditor_code           RH3006
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618008355
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C13 H9 Br O4 S'
_chemical_formula_moiety         'C13 H9 Br O4 S'
_chemical_formula_sum            'C13 H9 Br O4 S'
_chemical_formula_weight         341.17
_chemical_name_systematic
;
2-Formylphenyl 4-bromobenzenesulfonate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                91.249(3)
_cell_angle_beta                 102.818(2)
_cell_angle_gamma                95.938(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8282(5)
_cell_length_b                   8.5963(6)
_cell_length_c                   10.1139(6)
_cell_measurement_reflns_used    2262
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.158
_cell_measurement_theta_min      2.067
_cell_volume                     659.38(7)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>, 2008)
;
_computing_publication_material
;
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018  (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.80
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_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  0.0273
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10289
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.158
_diffrn_reflns_theta_min         2.067
_exptl_absorpt_coefficient_mu    3.281
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2007)
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.455
_refine_ls_extinction_coef       0.098(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.2877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0803
_reflns_number_gt                2262
_reflns_number_total             2877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            rh3006sup1.cif
_cod_data_source_block           3c
_cod_database_code               2021159
_cod_database_fobs_code          2021159
_shelx_estimated_absorpt_t_min   0.354
_shelx_estimated_absorpt_t_max   0.506
_shelx_hkl_checksum              35697
_shelx_res_checksum              23166