#------------------------------------------------------------------------------
#$Date: 2022-11-25 12:19:10 +0200 (Fri, 25 Nov 2022) $
#$Revision: 279566 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106260.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_8106260
loop_
_publ_author_name
'Cuicui, Huang'
'Shi, Maojian'
'Liu, Jing'
'Ding, Lin'
'Zhou, Jinhui'
_publ_section_title
;
 Crystal structure of 4-((1,3-dioxoisoindolin-2-yl)methyl)phenethyl
 4-methylbenzenesulfonate, C24H21NO5S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              683
_journal_page_last               684
_journal_paper_doi               10.1515/ncrs-2018-0010
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C24 H21 N O5 S'
_chemical_formula_sum            'C24 H21 N O5 S'
_chemical_formula_weight         435.48
_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
_cell_angle_alpha                90
_cell_angle_beta                 107.15(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7790(16)
_cell_length_b                   22.726(5)
_cell_length_c                   12.755(3)
_cell_measurement_reflns_used    1902
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      23
_cell_measurement_theta_min      2
_cell_volume                     2154.6(9)
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_collection       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34088
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.167
_diffrn_reflns_theta_min         3.890
_exptl_absorpt_coefficient_mu    1.640
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0453
_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/[σ²(Fo²)+(0.0535P)²+0.5450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2702
_reflns_number_total             3896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0010_suppl.cif
_cod_data_source_block           1
_cod_database_code               8106260
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.853
_shelx_estimated_absorpt_t_min   0.735
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.65559(9) 0.34733(3) 0.24221(5) 0.0699(2) Uani 1 1 d . . . . .
O1 O 0.4767(2) 0.36163(7) 0.15066(13) 0.0701(5) Uani 1 1 d . . . . .
O2 O 0.2664(3) 0.68074(9) 0.33844(17) 0.0888(6) Uani 1 1 d . . . . .
O3 O 0.6635(3) 0.64986(9) 0.14344(17) 0.0947(6) Uani 1 1 d . . . . .
O4 O 0.7887(3) 0.34565(9) 0.18642(18) 0.0937(6) Uani 1 1 d . . . . .
O5 O 0.6302(3) 0.29745(7) 0.30401(15) 0.0820(5) Uani 1 1 d . . . . .
N1 N 0.4295(3) 0.66102(8) 0.21802(16) 0.0631(5) Uani 1 1 d . . . . .
C1 C 0.3084(4) 0.35763(11) 0.1777(2) 0.0716(7) Uani 1 1 d . . . . .
H1A H 0.3219 0.3749 0.2492 0.086 Uiso 1 1 calc R . . . .
H1B H 0.2739 0.3167 0.1797 0.086 Uiso 1 1 calc R . . . .
C2 C 0.1663(4) 0.39033(11) 0.0910(2) 0.0753(7) Uani 1 1 d . . . . .
H2A H 0.0491 0.3814 0.0994 0.090 Uiso 1 1 calc R . . . .
H2B H 0.1673 0.3766 0.0192 0.090 Uiso 1 1 calc R . . . .
C3 C 0.1937(3) 0.45621(11) 0.0970(2) 0.0652(6) Uani 1 1 d . . . . .
C4 C 0.2810(4) 0.48491(12) 0.0334(2) 0.0750(7) Uani 1 1 d . . . . .
H4 H 0.3217 0.4636 -0.0169 0.090 Uiso 1 1 calc R . . . .
C5 C 0.3099(4) 0.54502(12) 0.0424(2) 0.0763(7) Uani 1 1 d . . . . .
H5 H 0.3714 0.5632 -0.0012 0.092 Uiso 1 1 calc R . . . .
C6 C 0.2499(3) 0.57843(11) 0.1140(2) 0.0658(6) Uani 1 1 d . . . . .
C7 C 0.2808(4) 0.64403(11) 0.1223(2) 0.0797(8) Uani 1 1 d . . . . .
H7A H 0.3061 0.6578 0.0564 0.096 Uiso 1 1 calc R . . . .
H7B H 0.1716 0.6633 0.1264 0.096 Uiso 1 1 calc R . . . .
C8 C 0.4073(3) 0.68039(10) 0.3166(2) 0.0659(6) Uani 1 1 d . . . . .
C9 C 0.5884(3) 0.69838(10) 0.3864(2) 0.0605(6) Uani 1 1 d . . . . .
C10 C 0.7083(3) 0.68803(10) 0.3277(2) 0.0617(6) Uani 1 1 d . . . . .
C11 C 0.6082(4) 0.66426(11) 0.2186(2) 0.0661(6) Uani 1 1 d . . . . .
C12 C 0.8890(4) 0.69958(12) 0.3721(3) 0.0829(8) Uani 1 1 d . . . . .
H12 H 0.9700 0.6928 0.3324 0.099 Uiso 1 1 calc R . . . .
C13 C 0.9460(4) 0.72160(13) 0.4778(3) 0.0937(10) Uani 1 1 d . . . . .
H13 H 1.0676 0.7293 0.5102 0.112 Uiso 1 1 calc R . . . .
C14 C 0.8263(5) 0.73219(13) 0.5355(3) 0.0947(10) Uani 1 1 d . . . . .
H14 H 0.8682 0.7474 0.6062 0.114 Uiso 1 1 calc R . . . .
C15 C 0.6434(4) 0.72084(12) 0.4910(2) 0.0810(8) Uani 1 1 d . . . . .
H15 H 0.5621 0.7281 0.5303 0.097 Uiso 1 1 calc R . . . .
C16 C 0.1563(4) 0.55021(12) 0.1761(2) 0.0772(7) Uani 1 1 d . . . . .
H16 H 0.1110 0.5719 0.2239 0.093 Uiso 1 1 calc R . . . .
C17 C 0.1292(4) 0.48979(12) 0.1677(2) 0.0764(7) Uani 1 1 d . . . . .
H17 H 0.0665 0.4715 0.2105 0.092 Uiso 1 1 calc R . . . .
C18 C 0.6882(3) 0.40947(10) 0.32704(19) 0.0636(6) Uani 1 1 d . . . . .
C19 C 0.7033(4) 0.46419(12) 0.2835(2) 0.0824(8) Uani 1 1 d . . . . .
H19 H 0.6936 0.4680 0.2094 0.099 Uiso 1 1 calc R . . . .
C20 C 0.7328(4) 0.51305(12) 0.3503(2) 0.0877(9) Uani 1 1 d . . . . .
H20 H 0.7431 0.5498 0.3205 0.105 Uiso 1 1 calc R . . . .
C21 C 0.7473(4) 0.50863(11) 0.4598(2) 0.0764(7) Uani 1 1 d . . . . .
C22 C 0.7303(4) 0.45350(12) 0.5019(2) 0.0843(8) Uani 1 1 d . . . . .
H22 H 0.7385 0.4497 0.5758 0.101 Uiso 1 1 calc R . . . .
C23 C 0.7014(4) 0.40377(11) 0.4360(2) 0.0752(7) Uani 1 1 d . . . . .
H23 H 0.6912 0.3670 0.4655 0.090 Uiso 1 1 calc R . . . .
C24 C 0.7813(5) 0.56234(13) 0.5339(3) 0.1015(10) Uani 1 1 d . . . . .
H24A H 0.9063 0.5640 0.5749 0.152 Uiso 1 1 calc GR . . . .
H24B H 0.7098 0.5598 0.5836 0.152 Uiso 1 1 calc GR . . . .
H24C H 0.7491 0.5972 0.4900 0.152 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3330 0.5570 '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_1
_geom_angle_site_symmetry_3
O1 S1 C18 103.21(10) . .
O4 S1 O1 104.55(11) . .
O4 S1 O5 119.73(12) . .
O4 S1 C18 109.70(12) . .
O5 S1 O1 109.85(11) . .
O5 S1 C18 108.52(12) . .
C1 O1 S1 118.41(15) . .
C8 N1 C7 124.0(2) . .
C11 N1 C7 124.1(2) . .
C11 N1 C8 111.7(2) . .
O1 C1 H1A 110.1 . .
O1 C1 H1B 110.1 . .
O1 C1 C2 108.2(2) . .
H1A C1 H1B 108.4 . .
C2 C1 H1A 110.1 . .
C2 C1 H1B 110.1 . .
C1 C2 H2A 109.0 . .
C1 C2 H2B 109.0 . .
C1 C2 C3 112.9(2) . .
H2A C2 H2B 107.8 . .
C3 C2 H2A 109.0 . .
C3 C2 H2B 109.0 . .
C4 C3 C2 122.0(3) . .
C4 C3 C17 117.6(2) . .
C17 C3 C2 120.5(2) . .
C3 C4 H4 119.4 . .
C3 C4 C5 121.2(3) . .
C5 C4 H4 119.4 . .
C4 C5 H5 119.2 . .
C6 C5 C4 121.5(3) . .
C6 C5 H5 119.2 . .
C5 C6 C7 121.0(3) . .
C5 C6 C16 117.7(2) . .
C16 C6 C7 121.2(3) . .
N1 C7 C6 112.9(2) . .
N1 C7 H7A 109.0 . .
N1 C7 H7B 109.0 . .
C6 C7 H7A 109.0 . .
C6 C7 H7B 109.0 . .
H7A C7 H7B 107.8 . .
O2 C8 N1 125.0(2) . .
O2 C8 C9 128.7(3) . .
N1 C8 C9 106.3(2) . .
C10 C9 C8 107.6(2) . .
C15 C9 C8 130.8(2) . .
C15 C9 C10 121.6(2) . .
C9 C10 C11 108.7(2) . .
C12 C10 C9 121.1(2) . .
C12 C10 C11 130.2(2) . .
O3 C11 N1 124.9(3) . .
O3 C11 C10 129.3(3) . .
N1 C11 C10 105.8(2) . .
C10 C12 H12 121.2 . .
C10 C12 C13 117.7(3) . .
C13 C12 H12 121.2 . .
C12 C13 H13 119.5 . .
C14 C13 C12 121.0(3) . .
C14 C13 H13 119.5 . .
C13 C14 H14 119.2 . .
C13 C14 C15 121.6(3) . .
C15 C14 H14 119.2 . .
C9 C15 C14 116.9(3) . .
C9 C15 H15 121.5 . .
C14 C15 H15 121.5 . .
C6 C16 H16 119.7 . .
C6 C16 C17 120.6(3) . .
C17 C16 H16 119.7 . .
C3 C17 C16 121.3(3) . .
C3 C17 H17 119.3 . .
C16 C17 H17 119.3 . .
C19 C18 S1 119.5(2) . .
C23 C18 S1 120.30(19) . .
C23 C18 C19 120.2(2) . .
C18 C19 H19 120.1 . .
C20 C19 C18 119.8(3) . .
C20 C19 H19 120.1 . .
C19 C20 H20 119.4 . .
C21 C20 C19 121.3(3) . .
C21 C20 H20 119.4 . .
C20 C21 C22 118.2(2) . .
C20 C21 C24 121.4(3) . .
C22 C21 C24 120.4(3) . .
C21 C22 H22 119.4 . .
C21 C22 C23 121.3(3) . .
C23 C22 H22 119.4 . .
C18 C23 C22 119.2(2) . .
C18 C23 H23 120.4 . .
C22 C23 H23 120.4 . .
C21 C24 H24A 109.5 . .
C21 C24 H24B 109.5 . .
C21 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.5645(18) .
S1 O4 1.419(2) .
S1 O5 1.4273(18) .
S1 C18 1.751(2) .
O1 C1 1.451(3) .
O2 C8 1.208(3) .
O3 C11 1.206(3) .
N1 C7 1.464(3) .
N1 C8 1.390(3) .
N1 C11 1.390(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C1 C2 1.508(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 C3 1.511(3) .
C3 C4 1.367(3) .
C3 C17 1.383(4) .
C4 H4 0.9300 .
C4 C5 1.384(4) .
C5 H5 0.9300 .
C5 C6 1.371(4) .
C6 C7 1.509(4) .
C6 C16 1.382(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.485(3) .
C9 C10 1.378(3) .
C9 C15 1.373(4) .
C10 C11 1.482(4) .
C10 C12 1.377(3) .
C12 H12 0.9300 .
C12 C13 1.383(4) .
C13 H13 0.9300 .
C13 C14 1.367(4) .
C14 H14 0.9300 .
C14 C15 1.392(4) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C16 C17 1.388(4) .
C17 H17 0.9300 .
C18 C19 1.381(3) .
C18 C23 1.369(3) .
C19 H19 0.9300 .
C19 C20 1.377(4) .
C20 H20 0.9300 .
C20 C21 1.372(4) .
C21 C22 1.385(4) .
C21 C24 1.518(4) .
C22 H22 0.9300 .
C22 C23 1.387(4) .
C23 H23 0.9300 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
S1 O1 C1 C2 162.99(16) . . . .
S1 C18 C19 C20 -178.6(2) . . . .
S1 C18 C23 C22 178.9(2) . . . .
O1 S1 C18 C19 -59.0(2) . . . .
O1 S1 C18 C23 122.1(2) . . . .
O1 C1 C2 C3 -70.3(3) . . . .
O2 C8 C9 C10 177.7(2) . . . .
O2 C8 C9 C15 -1.5(4) . . . .
O4 S1 O1 C1 170.71(17) . . . .
O4 S1 C18 C19 52.0(3) . . . .
O4 S1 C18 C23 -127.0(2) . . . .
O5 S1 O1 C1 41.04(19) . . . .
O5 S1 C18 C19 -175.5(2) . . . .
O5 S1 C18 C23 5.5(3) . . . .
N1 C8 C9 C10 -1.0(2) . . . .
N1 C8 C9 C15 179.7(2) . . . .
C1 C2 C3 C4 95.8(3) . . . .
C1 C2 C3 C17 -84.6(3) . . . .
C2 C3 C4 C5 -177.9(2) . . . .
C2 C3 C17 C16 178.6(2) . . . .
C3 C4 C5 C6 -1.1(4) . . . .
C4 C3 C17 C16 -1.7(4) . . . .
C4 C5 C6 C7 -179.4(2) . . . .
C4 C5 C6 C16 -1.1(4) . . . .
C5 C6 C7 N1 -101.7(3) . . . .
C5 C6 C16 C17 1.8(4) . . . .
C6 C16 C17 C3 -0.4(4) . . . .
C7 N1 C8 O2 6.7(4) . . . .
C7 N1 C8 C9 -174.5(2) . . . .
C7 N1 C11 O3 -5.2(4) . . . .
C7 N1 C11 C10 175.1(2) . . . .
C7 C6 C16 C17 -179.9(2) . . . .
C8 N1 C7 C6 -97.5(3) . . . .
C8 N1 C11 O3 179.6(2) . . . .
C8 N1 C11 C10 -0.1(3) . . . .
C8 C9 C10 C11 1.0(3) . . . .
C8 C9 C10 C12 -178.9(2) . . . .
C8 C9 C15 C14 178.5(2) . . . .
C9 C10 C11 O3 179.7(3) . . . .
C9 C10 C11 N1 -0.6(3) . . . .
C9 C10 C12 C13 0.3(4) . . . .
C10 C9 C15 C14 -0.6(4) . . . .
C10 C12 C13 C14 -0.8(4) . . . .
C11 N1 C7 C6 87.9(3) . . . .
C11 N1 C8 O2 -178.1(2) . . . .
C11 N1 C8 C9 0.7(2) . . . .
C11 C10 C12 C13 -179.5(3) . . . .
C12 C10 C11 O3 -0.4(5) . . . .
C12 C10 C11 N1 179.3(2) . . . .
C12 C13 C14 C15 0.6(5) . . . .
C13 C14 C15 C9 0.1(4) . . . .
C15 C9 C10 C11 -179.7(2) . . . .
C15 C9 C10 C12 0.4(4) . . . .
C16 C6 C7 N1 80.0(3) . . . .
C17 C3 C4 C5 2.4(4) . . . .
C18 S1 O1 C1 -74.54(18) . . . .
C18 C19 C20 C21 -0.1(5) . . . .
C19 C18 C23 C22 -0.1(4) . . . .
C19 C20 C21 C22 -0.4(5) . . . .
C19 C20 C21 C24 179.5(3) . . . .
C20 C21 C22 C23 0.7(5) . . . .
C21 C22 C23 C18 -0.5(4) . . . .
C23 C18 C19 C20 0.4(4) . . . .
C24 C21 C22 C23 -179.2(3) . . . .
