The crystal structures and Hirshfeld surface analysis of three new bromo-substituted 3-methyl-1-(phenylsulfonyl)-1H-indole derivatives
Madhan, S.; NizamMohideen, M.; Harikrishnan, K.; MohanaKrishnan, Arasambattu K.; Acta Crystallographica Section E Crystallographic Communications 80 (2024) 682–690; doi:10.1107/S2056989024004985

data_2023146
_publ_section_title
;
 The crystal structures and Hirshfeld surface analysis of three new
 bromo-substituted 3-methyl-1-(phenylsulfonyl)-1H-indole derivatives
;
_journal_coeditor_code           NU2005
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              682
_journal_page_last               690
_journal_paper_doi               10.1107/S2056989024004985
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C16 H14 Br N O2 S'
_chemical_formula_moiety         'C16 H14 Br N O2 S'
_chemical_formula_sum            'C16 H14 Br N O2 S'
_chemical_formula_weight         364.25
_chemical_name_systematic
;
2-(Bromomethyl)-3-methyl-1-(phenylsulfonyl)-1<i>H</i>-indole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 99.04(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.979(6)
_cell_length_b                   11.100(8)
_cell_length_c                   17.540(14)
_cell_measurement_reflns_used    66991
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.996
_cell_measurement_theta_min      1.403
_cell_volume                     1534(2)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON
(Spek, 2020)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
<i>SHELXS2018/3</i> (Sheldrick, 2008)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            66991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.042
_diffrn_reflns_theta_min         3.237
_diffrn_source                   'micro focus sealed tube'
_exptl_absorpt_coefficient_mu    2.819
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.797
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+1.2291P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                3158
_reflns_number_total             4464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nu2005.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2023146
_shelx_estimated_absorpt_t_min   0.489
_shelx_estimated_absorpt_t_max   0.836
_shelx_hkl_checksum              35553
_shelx_res_checksum              27923