Crystal engineering for intramolecular π–π stacking: effect of substitution of electron-donating and electron-withdrawing groups on the molecular geometry in conformationally flexible Sulfoesters and sulfonamides
Shaikh, Samir R.; Gawade, Rupesh L.; Dabke, Niteen B.; Dash, Soumya R.; Vanka, Kumar; Gonnade, Rajesh G.; CrystEngComm 26 (2024) 3557–3573; doi:10.1039/D4CE00309H

data_7248716
_publ_section_title
;
 Crystal engineering for intramolecular \p--\p stacking: effect of
 substitution of electron-donating and electron-withdrawing groups on the
 molecular geometry in conformationally flexible Sulfoesters and
 sulfonamides
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              3557
_journal_page_last               3573
_journal_paper_doi               10.1039/D4CE00309H
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C15 H14 N2 O2 S'
_chemical_formula_sum            'C15 H14 N2 O2 S'
_chemical_formula_weight         286.34
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'difference Fourier'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1812(6)
_cell_length_b                   5.7173(4)
_cell_length_c                   53.186(4)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.30
_cell_volume                     2791.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            16364
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         3.064
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.809
_refine_diff_density_min         -1.645
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4735
_refine_ls_number_restraints     145
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0886
_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^)+(0.0001P)^2^+25.2577P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2034
_refine_ls_wR_factor_ref         0.2042
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                4570
_reflns_number_total             4735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00309h2.cif
_cod_data_source_block           2b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'direct method' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7248707--7248724.cif.
;
_cod_database_code               7248716
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              75986