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_7230708
_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_formula_moiety         'C23 H23 N4 O3, CL, 2(H2 O)'
_chemical_formula_sum            'C23 H27 Cl N4 O3'
_chemical_formula_weight         442.93
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-08-25T13:57:20-00:00
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.5146(2)
_cell_length_b                   18.6958(3)
_cell_length_c                   30.8781(5)
_cell_measurement_reflns_used    20449
_cell_measurement_temperature    121(2)
_cell_measurement_theta_max      71.183
_cell_measurement_theta_min      4.727
_cell_volume                     4338.11(15)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      121(2)
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0015124
_diffrn_orient_matrix_UB_12      0.0754012
_diffrn_orient_matrix_UB_13      0.0201171
_diffrn_orient_matrix_UB_21      -0.0122533
_diffrn_orient_matrix_UB_22      -0.0331922
_diffrn_orient_matrix_UB_23      0.0455696
_diffrn_orient_matrix_UB_31      0.2046356
_diffrn_orient_matrix_UB_32      -0.0014305
_diffrn_orient_matrix_UB_33      0.0028797
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            63365
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.087
_diffrn_reflns_theta_min         4.731
_exptl_absorpt_coefficient_mu    1.831
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.59295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       plate
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0415P)^2^+6.7662P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0
_reflns_number_gt                3808
_reflns_number_total             4202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra03107j2.cif
_cod_data_source_block           1b
_cod_database_code               7230708
_shelx_estimated_absorpt_t_min   0.528
_shelx_estimated_absorpt_t_max   0.914