2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry
Caracelli, Ignez; Zukerman-Schpector, Julio; Traesel, Henrique J.; Olivato, Paulo R.; Jotani, Mukesh M.; Tiekink, Edward R. T.; Acta Crystallographica Section E 75 (2019) 816–822; doi:10.1107/S2056989019006765

data_2242940
_publ_section_title
;
 2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal
 structure, Hirshfeld surface analysis and computational chemistry
;
_journal_coeditor_code           HB7825
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              816
_journal_page_last               822
_journal_paper_doi               10.1107/S2056989019006765
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C15 H13 Br O2 S'
_chemical_formula_moiety         'C15 H13 Br O2 S'
_chemical_formula_sum            'C15 H13 Br O2 S'
_chemical_formula_weight         337.21
_chemical_name_systematic
;
2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_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           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0683(13)
_cell_length_b                   8.0190(6)
_cell_length_c                   9.8513(5)
_cell_measurement_reflns_used    1496
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.50
_cell_measurement_theta_min      2.78
_cell_volume                     1427.35(16)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
<i>MarvinSketch</i> (ChemAxon, 2010) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2014 (Burla <i>et al.</i>, 2015)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0875
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6329
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         2.254
_exptl_absorpt_coefficient_mu    3.020
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       irregular
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.359
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 702 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al</i>., 2013)
;
_refine_ls_abs_structure_Flack   0.013(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.902
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0354
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                1903
_reflns_number_total             2820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7825sup1.cif
_cod_data_source_block           I
_cod_database_code               2242940
_cod_database_fobs_code          2242940
_shelx_estimated_absorpt_t_min   0.333
_shelx_estimated_absorpt_t_max   0.677
_shelx_hkl_checksum              4438
_shelx_res_checksum              13918
_shelxl_version_number           2014/6