The effect of the intramolecular C–H⋯O interactions on the conformational preferences of bis-arylsulfones – 5-HT6 receptor antagonists and beyond
Kalinowska-Tłuścik, Justyna; Staroń, Jakub; Krawczuk, Anna; Mordalski, Stefan; Warszycki, Dawid; Satała, Grzegorz; Hogendorf, Adam S.; Bojarski, Andrzej J.; RSC Advances 8 (2018) 18672–; doi:10.1039/C8RA03107J

data_7230712
_publ_section_title
;
 The effect of the intramolecular C--H&#x22EF;O interactions on the
 conformational preferences of bis-arylsulfones -- 5-HT6 receptor
 antagonists and beyond
;
_journal_issue                   33
_journal_name_full               'RSC Advances'
_journal_page_first              18672
_journal_paper_doi               10.1039/C8RA03107J
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H25 N4, C2HO4'
_chemical_formula_sum            'C25 H26 N4 O4'
_chemical_formula_weight         446.5
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_space_group_name_H-M   'I 1 a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-02-23T23:32:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2017-05-15 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.85(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5126(19)
_cell_length_b                   22.934(16)
_cell_length_c                   11.454(4)
_cell_measurement_reflns_used    2209
_cell_measurement_temperature    130(1)
_cell_measurement_theta_max      28.6339
_cell_measurement_theta_min      3.2166
_cell_volume                     2196.2(18)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130(1)
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0230206
_diffrn_orient_matrix_UB_12      -0.0264485
_diffrn_orient_matrix_UB_13      -0.0305057
_diffrn_orient_matrix_UB_21      0.0120381
_diffrn_orient_matrix_UB_22      -0.0150794
_diffrn_orient_matrix_UB_23      0.0550818
_diffrn_orient_matrix_UB_31      -0.0807148
_diffrn_orient_matrix_UB_32      0.005274
_diffrn_orient_matrix_UB_33      0.0044576
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.175
_diffrn_reflns_av_unetI/netI     0.2016
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13886
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.9
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.682
_diffrn_reflns_theta_min         3.222
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.30665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.35
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 588 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5103
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.2077
_refine_ls_R_factor_gt           0.0789
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0669P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1682
_refine_ls_wR_factor_ref         0.2356
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                1906
_reflns_number_total             5103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra03107j2.cif
_cod_data_source_block           1c
_cod_original_sg_symbol_H-M      'I a'
_cod_database_code               7230712
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.995