#------------------------------------------------------------------------------
#$Date: 2018-05-22 18:05:36 +0300 (Tue, 22 May 2018) $
#$Revision: 207900 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/07/7230709.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7230709
loop_
_publ_author_name
'Kalinowska-Tłuścik, Justyna'
'Staroń, Jakub'
'Krawczuk, Anna'
'Mordalski, Stefan'
'Warszycki, Dawid'
'Satała, Grzegorz'
'Hogendorf, Adam S.'
'Bojarski, Andrzej J.'
_publ_section_title
;
 The effect of the intramolecular C--H⋯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         'C20 H25 N2 O3, C2 H O4'
_chemical_formula_sum            'C22 H26 N2 O5'
_chemical_formula_weight         398.45
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-08-25T17:30:42-00:00
_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                114.544(5)
_cell_angle_beta                 92.599(4)
_cell_angle_gamma                112.821(5)
_cell_formula_units_Z            2
_cell_length_a                   9.1897(4)
_cell_length_b                   11.1766(6)
_cell_length_c                   11.9074(7)
_cell_measurement_reflns_used    6022
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6452
_cell_measurement_theta_min      3.4117
_cell_volume                     993.84(12)
_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      293(2)
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.9
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0820425
_diffrn_orient_matrix_UB_12      0.0549641
_diffrn_orient_matrix_UB_13      0.0228588
_diffrn_orient_matrix_UB_21      -0.0164036
_diffrn_orient_matrix_UB_22      0.0290783
_diffrn_orient_matrix_UB_23      -0.0391458
_diffrn_orient_matrix_UB_31      -0.0215594
_diffrn_orient_matrix_UB_32      0.0471149
_diffrn_orient_matrix_UB_33      0.0501008
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.9
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.708
_diffrn_reflns_theta_min         3.419
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.88442
_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    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0403P)²+0.3921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1208
_reflns_Friedel_coverage         0
_reflns_number_gt                3571
_reflns_number_total             4623
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ra03107j2.cif
_cod_data_source_block           2c
_cod_original_cell_volume        993.84(10)
_cod_database_code               7230709
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.986
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O31 O 0.03016(15) 0.12982(13) 0.44718(12) 0.0447(3) Uani 1 1 d . .
O32 O -0.16070(16) 0.04165(14) 0.53932(14) 0.0544(4) Uani 1 1 d . .
C30 C -0.04193(19) 0.04753(16) 0.49869(15) 0.0350(3) Uani 1 1 d . .
H31 H -0.012(3) 0.203(3) 0.454(2) 0.096(8) Uiso 1 1 d . .
O22 O -0.07536(14) 0.31663(12) 0.46732(13) 0.0469(3) Uani 1 1 d . .
N33 N 0.40567(17) 0.72454(14) 0.49189(12) 0.0348(3) Uani 1 1 d . .
O21 O 0.16944(15) 0.46839(13) 0.46877(13) 0.0507(3) Uani 1 1 d . .
C9 C 0.17470(18) 0.61679(17) -0.04713(16) 0.0375(4) Uani 1 1 d . .
N1 N 0.14629(17) 0.72826(15) 0.03985(14) 0.0419(3) Uani 1 1 d . .
C5 C 0.27427(19) 0.44474(18) -0.04610(15) 0.0381(4) Uani 1 1 d . .
H5 H 0.3165 0.4078 -0.0031 0.046 Uiso 1 1 calc R U
O61 O 0.27260(18) 0.26746(16) -0.25453(12) 0.0599(4) Uani 1 1 d . .
C20 C 0.02847(19) 0.43843(16) 0.48101(15) 0.0344(3) Uani 1 1 d . .
C4 C 0.23622(18) 0.56179(16) 0.02020(15) 0.0346(3) Uani 1 1 d . .
C6 C 0.2472(2) 0.38615(19) -0.17684(16) 0.0434(4) Uani 1 1 d . .
C32 C 0.3681(2) 0.75394(17) 0.38492(15) 0.0367(3) Uani 1 1 d . .
H32B H 0.4673 0.8265 0.3821 0.044 Uiso 1 1 calc R U
H32A H 0.2913 0.7953 0.4017 0.044 Uiso 1 1 calc R U
C3 C 0.24388(19) 0.64387(17) 0.15173(15) 0.0358(3) Uani 1 1 d . .
C11 C 0.17995(19) 0.96880(18) 0.06270(16) 0.0386(4) Uani 1 1 d . .
C31 C 0.2976(2) 0.61765(18) 0.25664(15) 0.0407(4) Uani 1 1 d . .
H31B H 0.3789 0.5823 0.2358 0.049 Uiso 1 1 calc R U
H31A H 0.2051 0.5415 0.262 0.049 Uiso 1 1 calc R U
C8 C 0.1546(2) 0.5605(2) -0.17870(17) 0.0465(4) Uani 1 1 d . .
H8 H 0.1179 0.5999 -0.2222 0.056 Uiso 1 1 calc R U
C10 C 0.0693(2) 0.8076(2) 0.0108(2) 0.0502(4) Uani 1 1 d . .
H10A H -0.0257 0.7963 0.0456 0.06 Uiso 1 1 calc R U
H10B H 0.0323 0.7636 -0.081 0.06 Uiso 1 1 calc R U
C35 C 0.5321(2) 0.6713(2) 0.47918(18) 0.0502(4) Uani 1 1 d . .
H35C H 0.4987 0.5852 0.3983 0.075 Uiso 1 1 calc R U
H35B H 0.6333 0.7468 0.4846 0.075 Uiso 1 1 calc R U
H35A H 0.5461 0.6475 0.5464 0.075 Uiso 1 1 calc R U
C2 C 0.1871(2) 0.74225(18) 0.15868(16) 0.0410(4) Uani 1 1 d . .
H2 H 0.1774 0.8093 0.2333 0.049 Uiso 1 1 calc R U
C7 C 0.1906(2) 0.4451(2) -0.24185(17) 0.0485(4) Uani 1 1 d . .
H7 H 0.1772 0.4054 -0.3296 0.058 Uiso 1 1 calc R U
C34 C 0.4560(3) 0.8578(2) 0.61663(17) 0.0520(5) Uani 1 1 d . .
H34B H 0.3738 0.8916 0.6242 0.078 Uiso 1 1 calc R U
H34C H 0.4699 0.8344 0.6841 0.078 Uiso 1 1 calc R U
H34A H 0.5571 0.9336 0.6223 0.078 Uiso 1 1 calc R U
C62 C 0.3138(2) 0.1935(2) -0.19728(19) 0.0546(5) Uani 1 1 d . .
H62C H 0.3282 0.1137 -0.2605 0.082 Uiso 1 1 calc R U
H62B H 0.4132 0.2607 -0.132 0.082 Uiso 1 1 calc R U
H62A H 0.228 0.1555 -0.1603 0.082 Uiso 1 1 calc R U
C12 C 0.3122(2) 1.0156(2) 0.0148(2) 0.0545(5) Uani 1 1 d . .
H12 H 0.3333 0.9471 -0.0506 0.065 Uiso 1 1 calc R U
C16 C 0.1520(2) 1.0739(2) 0.15948(18) 0.0531(5) Uani 1 1 d . .
H16 H 0.0642 1.0444 0.194 0.064 Uiso 1 1 calc R U
C15 C 0.2528(3) 1.2226(2) 0.2058(2) 0.0699(7) Uani 1 1 d . .
H15 H 0.2312 1.2922 0.2696 0.084 Uiso 1 1 calc R U
C14 C 0.3831(3) 1.2663(2) 0.1578(3) 0.0764(7) Uani 1 1 d . .
H14 H 0.4515 1.3659 0.1894 0.092 Uiso 1 1 calc R U
C13 C 0.4142(3) 1.1645(3) 0.0636(3) 0.0711(7) Uani 1 1 d . .
H13 H 0.5044 1.1951 0.0317 0.085 Uiso 1 1 calc R U
H6 H 0.314(2) 0.652(2) 0.4903(17) 0.046(5) Uiso 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C30 O31 H31 113.9(15) .
O32 C30 O31 126.00(14) .
O32 C30 C30 122.09(18) 2_556
O31 C30 C30 111.90(16) 2_556
C34 N33 C35 109.95(14) .
C34 N33 C32 110.71(13) .
C35 N33 C32 112.77(13) .
C34 N33 H6 108.2(11) .
C35 N33 H6 106.8(12) .
C32 N33 H6 108.2(12) .
N1 C9 C8 130.98(16) .
N1 C9 C4 107.60(14) .
C8 C9 C4 121.41(16) .
C2 N1 C9 108.36(13) .
C2 N1 C10 125.02(15) .
C9 N1 C10 126.30(15) .
C6 C5 C4 118.15(15) .
C6 C5 H5 120.9 .
C4 C5 H5 120.9 .
C6 O61 C62 117.27(14) .
O21 C20 O22 126.03(14) .
O21 C20 C20 118.31(16) 2_566
O22 C20 C20 115.65(17) 2_566
C9 C4 C5 119.72(14) .
C9 C4 C3 107.32(14) .
C5 C4 C3 132.96(15) .
C5 C6 O61 124.42(16) .
C5 C6 C7 121.34(16) .
O61 C6 C7 114.23(15) .
N33 C32 C31 113.09(12) .
N33 C32 H32B 109 .
C31 C32 H32B 109 .
N33 C32 H32A 109 .
C31 C32 H32A 109 .
H32B C32 H32A 107.8 .
C2 C3 C4 106.28(14) .
C2 C3 C31 128.68(15) .
C4 C3 C31 124.98(14) .
C12 C11 C16 118.21(17) .
C12 C11 C10 120.68(17) .
C16 C11 C10 121.11(17) .
C3 C31 C32 113.05(13) .
C3 C31 H31B 109 .
C32 C31 H31B 109 .
C3 C31 H31A 109 .
C32 C31 H31A 109 .
H31B C31 H31A 107.8 .
C7 C8 C9 117.94(16) .
C7 C8 H8 121 .
C9 C8 H8 121 .
N1 C10 C11 113.55(14) .
N1 C10 H10A 108.9 .
C11 C10 H10A 108.9 .
N1 C10 H10B 108.9 .
C11 C10 H10B 108.9 .
H10A C10 H10B 107.7 .
N33 C35 H35C 109.5 .
N33 C35 H35B 109.5 .
H35C C35 H35B 109.5 .
N33 C35 H35A 109.5 .
H35C C35 H35A 109.5 .
H35B C35 H35A 109.5 .
C3 C2 N1 110.43(15) .
C3 C2 H2 124.8 .
N1 C2 H2 124.8 .
C8 C7 C6 121.34(16) .
C8 C7 H7 119.3 .
C6 C7 H7 119.3 .
N33 C34 H34B 109.5 .
N33 C34 H34C 109.5 .
H34B C34 H34C 109.5 .
N33 C34 H34A 109.5 .
H34B C34 H34A 109.5 .
H34C C34 H34A 109.5 .
O61 C62 H62C 109.5 .
O61 C62 H62B 109.5 .
H62C C62 H62B 109.5 .
O61 C62 H62A 109.5 .
H62C C62 H62A 109.5 .
H62B C62 H62A 109.5 .
C11 C12 C13 120.4(2) .
C11 C12 H12 119.8 .
C13 C12 H12 119.8 .
C11 C16 C15 121.0(2) .
C11 C16 H16 119.5 .
C15 C16 H16 119.5 .
C14 C15 C16 119.8(2) .
C14 C15 H15 120.1 .
C16 C15 H15 120.1 .
C15 C14 C13 120.2(2) .
C15 C14 H14 119.9 .
C13 C14 H14 119.9 .
C14 C13 C12 120.4(2) .
C14 C13 H13 119.8 .
C12 C13 H13 119.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O31 C30 1.3015(18) .
O31 H31 1.01(3) .
O32 C30 1.2035(19) .
C30 C30 1.544(3) 2_556
O22 C20 1.2586(18) .
N33 C34 1.485(2) .
N33 C35 1.485(2) .
N33 C32 1.498(2) .
N33 H6 0.908(19) .
O21 C20 1.2381(19) .
C9 N1 1.378(2) .
C9 C8 1.396(2) .
C9 C4 1.406(2) .
N1 C2 1.375(2) .
N1 C10 1.458(2) .
C5 C6 1.381(2) .
C5 C4 1.407(2) .
C5 H5 0.93 .
O61 C6 1.382(2) .
O61 C62 1.407(2) .
C20 C20 1.561(3) 2_566
C4 C3 1.430(2) .
C6 C7 1.399(3) .
C32 C31 1.512(2) .
C32 H32B 0.97 .
C32 H32A 0.97 .
C3 C2 1.364(2) .
C3 C31 1.500(2) .
C11 C12 1.376(3) .
C11 C16 1.382(2) .
C11 C10 1.503(2) .
C31 H31B 0.97 .
C31 H31A 0.97 .
C8 C7 1.373(3) .
C8 H8 0.93 .
C10 H10A 0.97 .
C10 H10B 0.97 .
C35 H35C 0.96 .
C35 H35B 0.96 .
C35 H35A 0.96 .
C2 H2 0.93 .
C7 H7 0.93 .
C34 H34B 0.96 .
C34 H34C 0.96 .
C34 H34A 0.96 .
C62 H62C 0.96 .
C62 H62B 0.96 .
C62 H62A 0.96 .
C12 C13 1.386(3) .
C12 H12 0.93 .
C16 C15 1.387(3) .
C16 H16 0.93 .
C15 C14 1.356(4) .
C15 H15 0.93 .
C14 C13 1.362(4) .
C14 H14 0.93 .
C13 H13 0.93 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O31 H31 O22 1.01(3) 1.55(3) 2.5560(16) 179(3) .
C32 H32A O32 0.97 2.44 3.3893(19) 165.3 2_566
C2 H2 O32 0.93 2.57 3.485(2) 166.8 2_566
C34 H34B O22 0.96 2.61 3.132(2) 114.8 2_566
N33 H6 O22 0.908(19) 2.391(18) 2.9829(18) 122.9(14) 2_566
N33 H6 O21 0.908(19) 1.86(2) 2.7304(18) 159.6(17) .
O31 H31 O22 1.01(3) 1.55(3) 2.5560(16) 179(3) .
C32 H32A O32 0.97 2.44 3.3893(19) 165.3 2_566
C2 H2 O32 0.93 2.57 3.485(2) 166.8 2_566
C34 H34B O22 0.96 2.61 3.132(2) 114.8 2_566
N33 H6 O22 0.908(19) 2.391(18) 2.9829(18) 122.9(14) 2_566
N33 H6 O21 0.908(19) 1.86(2) 2.7304(18) 159.6(17) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 C9 N1 C2 -179.42(17)
C4 C9 N1 C2 -0.61(17)
C8 C9 N1 C10 6.9(3)
C4 C9 N1 C10 -174.31(15)
N1 C9 C4 C5 179.20(13)
C8 C9 C4 C5 -1.9(2)
N1 C9 C4 C3 0.14(17)
C8 C9 C4 C3 179.08(15)
C6 C5 C4 C9 -0.9(2)
C6 C5 C4 C3 177.87(16)
C4 C5 C6 O61 -177.26(15)
C4 C5 C6 C7 2.9(2)
C62 O61 C6 C5 6.3(3)
C62 O61 C6 C7 -173.81(16)
C34 N33 C32 C31 -173.38(15)
C35 N33 C32 C31 62.96(19)
C9 C4 C3 C2 0.38(17)
C5 C4 C3 C2 -178.51(16)
C9 C4 C3 C31 177.91(15)
C5 C4 C3 C31 -1.0(3)
C2 C3 C31 C32 -29.9(2)
C4 C3 C31 C32 153.13(15)
N33 C32 C31 C3 173.99(13)
N1 C9 C8 C7 -178.76(16)
C4 C9 C8 C7 2.6(2)
C2 N1 C10 C11 70.7(2)
C9 N1 C10 C11 -116.62(18)
C12 C11 C10 N1 67.9(2)
C16 C11 C10 N1 -112.14(19)
C4 C3 C2 N1 -0.77(18)
C31 C3 C2 N1 -178.18(15)
C9 N1 C2 C3 0.88(19)
C10 N1 C2 C3 174.68(15)
C9 C8 C7 C6 -0.6(3)
C5 C6 C7 C8 -2.2(3)
O61 C6 C7 C8 177.93(16)
C16 C11 C12 C13 0.3(3)
C10 C11 C12 C13 -179.71(18)
C12 C11 C16 C15 1.0(3)
C10 C11 C16 C15 -178.99(17)
C11 C16 C15 C14 -1.5(3)
C16 C15 C14 C13 0.6(3)
C15 C14 C13 C12 0.7(3)
C11 C12 C13 C14 -1.2(3)
