Complex Electronic interplay of -hole and π-hole interactions in crystals of halogen substituted 1,3,4-oxadiazol-2(3H)-thiones
shukla, rahul; Khan, Imtiaz; Ibrar, Aliya; Simpson, Jim; Chopra, Deepak; CrystEngComm  (2017) –; doi:10.1039/C7CE00678K

data_7228310
_publ_section_title
;
 Complex Electronic interplay of &#xF073;-hole and \p-hole interactions in
 crystals of halogen substituted 1,3,4-oxadiazol-2(3H)-thiones
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00678K
_journal_year                    2017
_chemical_formula_moiety         'C9 H7 Cl N2 O S'
_chemical_formula_sum            'C9 H7 Cl N2 O S'
_chemical_formula_weight         226.68
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-19 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8187(3)
_cell_length_b                   9.7550(6)
_cell_length_c                   20.3555(13)
_cell_measurement_reflns_used    5612
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      32.51
_cell_measurement_theta_min      2.89
_cell_volume                     956.84(10)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_structure_refinement
'SHELXL-2014/7 (Sheldrick, 2014) & TITAN (Hunter & Simpson, 1999)'
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10092
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        31.500
_diffrn_reflns_theta_max         33.334
_diffrn_reflns_theta_min         2.315
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular plate'
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1178 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0347P)^2^+0.0475P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0677
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                3088
_reflns_number_total             3294
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00678k2.cif
_cod_data_source_block           OT2
_cod_database_code               7228310
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.760
_shelx_estimated_absorpt_t_max   0.918
_shelx_res_checksum              99364