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#$Date: 2023-06-09 10:14:07 +0300 (Fri, 09 Jun 2023) $
#$Revision: 284426 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107331.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_8107331
loop_
_publ_author_name
'Zhang, Zhenguo'
'Yuan, Changchun'
'Xun, Miao-Miao'
'Fu, Kai'
_publ_section_title
;
 Crystal structure of 2-hydroxy-1-tosylindolin-3-yl- 2-naphthoate,
 C26H21N1S1O5
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1193
_journal_page_last               1194
_journal_paper_doi               10.1515/ncrs-2022-0452
_journal_volume                  237
_journal_year                    2022
_chemical_formula_sum            'C26 H21 N O5 S'
_chemical_formula_weight         459.50
_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
_cell_angle_alpha                90
_cell_angle_beta                 100.073(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.623(3)
_cell_length_b                   25.617(12)
_cell_length_c                   11.775(5)
_cell_measurement_reflns_used    4587
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      1.59
_cell_volume                     2264.0(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12292
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.340
_diffrn_reflns_theta_min         1.590
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_correction_T_min  0.9587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0867P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3363
_reflns_number_total             4587
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0452_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        2264.2(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107331
_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_min   0.959
_shelx_estimated_absorpt_t_max   0.979
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 0.20654(6) 0.42815(2) 0.62890(4) 0.05140(17) Uani 1 1 d . . . . .
N1 N 0.08166(19) 0.44465(5) 0.72203(12) 0.0479(4) Uani 1 1 d . . . . .
O1 O -0.19596(16) 0.36414(4) 0.77700(10) 0.0492(3) Uani 1 1 d . . . . .
O2 O -0.3400(2) 0.35664(5) 0.92738(12) 0.0662(4) Uani 1 1 d . . . . .
O3 O -0.18949(17) 0.49181(5) 0.66884(10) 0.0601(4) Uani 1 1 d . . . . .
H3A H -0.159611 0.503996 0.610708 0.090 Uiso 1 1 calc R U . . .
O4 O 0.1227(2) 0.45117(5) 0.52270(12) 0.0734(5) Uani 1 1 d . . . . .
O5 O 0.38630(18) 0.44113(6) 0.67757(15) 0.0741(4) Uani 1 1 d . . . . .
C1 C -0.2778(2) 0.33663(7) 0.85025(14) 0.0473(4) Uani 1 1 d . . . . .
C2 C -0.2815(2) 0.27996(7) 0.82437(14) 0.0448(4) Uani 1 1 d . . . . .
C3 C -0.3489(2) 0.24645(7) 0.89787(14) 0.0464(4) Uani 1 1 d . . . . .
H3B H -0.389240 0.259928 0.961968 0.056 Uiso 1 1 calc R U . . .
C4 C -0.3577(2) 0.19178(7) 0.87752(14) 0.0455(4) Uani 1 1 d . . . . .
C5 C -0.4237(3) 0.15641(7) 0.95265(16) 0.0565(5) Uani 1 1 d . . . . .
H5B H -0.462332 0.169033 1.018095 0.068 Uiso 1 1 calc R U . . .
C6 C -0.4312(3) 0.10409(8) 0.93024(19) 0.0675(6) Uani 1 1 d . . . . .
H6A H -0.474571 0.081447 0.980520 0.081 Uiso 1 1 calc R U . . .
C7 C -0.3742(3) 0.08438(9) 0.8324(2) 0.0750(6) Uani 1 1 d . . . . .
H7A H -0.380589 0.048709 0.817562 0.090 Uiso 1 1 calc R U . . .
C8 C -0.3091(3) 0.11710(8) 0.75829(19) 0.0715(6) Uani 1 1 d . . . . .
H8A H -0.271584 0.103459 0.693347 0.086 Uiso 1 1 calc R U . . .
C9 C -0.2977(3) 0.17186(7) 0.77908(15) 0.0525(5) Uani 1 1 d . . . . .
C10 C -0.2290(3) 0.20742(8) 0.70580(16) 0.0614(5) Uani 1 1 d . . . . .
H10A H -0.188766 0.194703 0.640962 0.074 Uiso 1 1 calc R U . . .
C11 C -0.2201(3) 0.25927(7) 0.72729(15) 0.0534(5) Uani 1 1 d . . . . .
H11A H -0.173156 0.281482 0.677762 0.064 Uiso 1 1 calc R U . . .
C12 C 0.1302(3) 0.44137(7) 0.84494(15) 0.0485(4) Uani 1 1 d . . . . .
C13 C 0.2956(3) 0.45032(8) 0.9137(2) 0.0710(6) Uani 1 1 d . . . . .
H13A H 0.396201 0.457214 0.881538 0.085 Uiso 1 1 calc R U . . .
C14 C 0.3039(4) 0.44852(9) 1.0319(2) 0.0869(8) Uani 1 1 d . . . . .
H14A H 0.413218 0.453302 1.079937 0.104 Uiso 1 1 calc R U . . .
C15 C 0.1554(4) 0.43988(8) 1.08009(19) 0.0795(8) Uani 1 1 d . . . . .
H15A H 0.164693 0.440005 1.159897 0.095 Uiso 1 1 calc R U . . .
C16 C -0.0081(3) 0.43097(7) 1.01112(16) 0.0637(6) Uani 1 1 d . . . . .
H16A H -0.108688 0.425154 1.044049 0.076 Uiso 1 1 calc R U . . .
C17 C -0.0203(3) 0.43081(6) 0.89223(14) 0.0477(4) Uani 1 1 d . . . . .
C18 C -0.1754(2) 0.42023(6) 0.79728(14) 0.0460(4) Uani 1 1 d . . . . .
H18A H -0.285486 0.436547 0.812048 0.055 Uiso 1 1 calc R U . . .
C19 C -0.1162(2) 0.44213(7) 0.68971(14) 0.0449(4) Uani 1 1 d . . . . .
H19A H -0.152283 0.419129 0.623230 0.054 Uiso 1 1 calc R U . . .
C20 C 0.2708(3) 0.32747(7) 0.69876(17) 0.0585(5) Uani 1 1 d . . . . .
H20A H 0.321150 0.341193 0.770168 0.070 Uiso 1 1 calc R U . . .
C21 C 0.2714(3) 0.27410(8) 0.6793(2) 0.0700(6) Uani 1 1 d . . . . .
H21A H 0.321934 0.252058 0.738908 0.084 Uiso 1 1 calc R U . . .
C22 C 0.1990(3) 0.25287(8) 0.5740(2) 0.0722(6) Uani 1 1 d . . . . .
C23 C 0.1206(3) 0.28589(9) 0.4879(2) 0.0758(6) Uani 1 1 d . . . . .
H23A H 0.069174 0.272022 0.416909 0.091 Uiso 1 1 calc R U . . .
C24 C 0.1164(3) 0.33910(8) 0.50450(17) 0.0617(5) Uani 1 1 d . . . . .
H24A H 0.061833 0.360817 0.445430 0.074 Uiso 1 1 calc R U . . .
C25 C 0.1940(2) 0.35997(7) 0.60985(15) 0.0456(4) Uani 1 1 d . . . . .
C26 C 0.2100(4) 0.19435(9) 0.5533(3) 0.1151(11) Uani 1 1 d . . . . .
H26A H 0.268659 0.177638 0.622601 0.173 Uiso 1 1 calc R U . . .
H26B H 0.091952 0.180390 0.531875 0.173 Uiso 1 1 calc R U . . .
H26C H 0.276226 0.188146 0.492393 0.173 Uiso 1 1 calc R U . . .
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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
O4 S1 O5 120.40(10) . .
O4 S1 N1 104.93(9) . .
O5 S1 N1 107.58(9) . .
O4 S1 C25 106.97(9) . .
O5 S1 C25 107.97(8) . .
N1 S1 C25 108.53(8) . .
C12 N1 C19 109.05(14) . .
C12 N1 S1 125.95(13) . .
C19 N1 S1 120.08(11) . .
C1 O1 C18 117.26(13) . .
C19 O3 H3A 109.5 . .
O2 C1 O1 123.03(17) . .
O2 C1 C2 124.97(16) . .
O1 C1 C2 112.00(15) . .
C3 C2 C11 119.11(17) . .
C3 C2 C1 118.42(16) . .
C11 C2 C1 122.47(15) . .
C2 C3 C4 121.28(17) . .
C2 C3 H3B 119.4 . .
C4 C3 H3B 119.4 . .
C9 C4 C5 118.79(17) . .
C9 C4 C3 118.79(15) . .
C5 C4 C3 122.42(16) . .
C6 C5 C4 120.93(18) . .
C6 C5 H5B 119.5 . .
C4 C5 H5B 119.5 . .
C5 C6 C7 120.41(19) . .
C5 C6 H6A 119.8 . .
C7 C6 H6A 119.8 . .
C8 C7 C6 120.4(2) . .
C8 C7 H7A 119.8 . .
C6 C7 H7A 119.8 . .
C7 C8 C9 120.9(2) . .
C7 C8 H8A 119.6 . .
C9 C8 H8A 119.6 . .
C4 C9 C10 118.33(17) . .
C4 C9 C8 118.55(17) . .
C10 C9 C8 123.13(18) . .
C11 C10 C9 121.98(18) . .
C11 C10 H10A 119.0 . .
C9 C10 H10A 119.0 . .
C10 C11 C2 120.50(17) . .
C10 C11 H11A 119.7 . .
C2 C11 H11A 119.7 . .
C17 C12 C13 121.78(19) . .
C17 C12 N1 109.37(16) . .
C13 C12 N1 128.72(19) . .
C14 C13 C12 117.2(2) . .
C14 C13 H13A 121.4 . .
C12 C13 H13A 121.4 . .
C15 C14 C13 121.8(2) . .
C15 C14 H14A 119.1 . .
C13 C14 H14A 119.1 . .
C14 C15 C16 120.6(2) . .
C14 C15 H15A 119.7 . .
C16 C15 H15A 119.7 . .
C15 C16 C17 119.2(2) . .
C15 C16 H16A 120.4 . .
C17 C16 H16A 120.4 . .
C12 C17 C16 119.40(19) . .
C12 C17 C18 109.57(15) . .
C16 C17 C18 131.03(19) . .
O1 C18 C17 110.30(13) . .
O1 C18 C19 105.38(13) . .
C17 C18 C19 104.06(14) . .
O1 C18 H18A 112.2 . .
C17 C18 H18A 112.2 . .
C19 C18 H18A 112.2 . .
O3 C19 N1 111.21(14) . .
O3 C19 C18 108.34(13) . .
N1 C19 C18 103.72(13) . .
O3 C19 H19A 111.1 . .
N1 C19 H19A 111.1 . .
C18 C19 H19A 111.1 . .
C25 C20 C21 118.77(19) . .
C25 C20 H20A 120.6 . .
C21 C20 H20A 120.6 . .
C22 C21 C20 121.7(2) . .
C22 C21 H21A 119.2 . .
C20 C21 H21A 119.2 . .
C23 C22 C21 118.35(19) . .
C23 C22 C26 121.1(2) . .
C21 C22 C26 120.5(2) . .
C22 C23 C24 121.5(2) . .
C22 C23 H23A 119.2 . .
C24 C23 H23A 119.2 . .
C23 C24 C25 119.45(19) . .
C23 C24 H24A 120.3 . .
C25 C24 H24A 120.3 . .
C24 C25 C20 120.20(18) . .
C24 C25 S1 120.13(14) . .
C20 C25 S1 119.57(14) . .
C22 C26 H26A 109.5 . .
C22 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C22 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O4 1.4285(15) .
S1 O5 1.4290(16) .
S1 N1 1.6287(16) .
S1 C25 1.761(2) .
N1 C12 1.432(2) .
N1 C19 1.491(2) .
O1 C1 1.348(2) .
O1 C18 1.461(2) .
O2 C1 1.210(2) .
O3 C19 1.394(2) .
O3 H3A 0.8200 .
C1 C2 1.483(3) .
C2 C3 1.380(2) .
C2 C11 1.412(2) .
C3 C4 1.421(2) .
C3 H3B 0.9300 .
C4 C9 1.414(3) .
C4 C5 1.419(2) .
C5 C6 1.365(3) .
C5 H5B 0.9300 .
C6 C7 1.395(3) .
C6 H6A 0.9300 .
C7 C8 1.364(3) .
C7 H7A 0.9300 .
C8 C9 1.424(3) .
C8 H8A 0.9300 .
C9 C10 1.417(3) .
C10 C11 1.352(3) .
C10 H10A 0.9300 .
C11 H11A 0.9300 .
C12 C17 1.386(3) .
C12 C13 1.393(3) .
C13 C14 1.382(4) .
C13 H13A 0.9300 .
C14 C15 1.370(4) .
C14 H14A 0.9300 .
C15 C16 1.382(3) .
C15 H15A 0.9300 .
C16 C17 1.387(3) .
C16 H16A 0.9300 .
C17 C18 1.503(3) .
C18 C19 1.524(2) .
C18 H18A 0.9800 .
C19 H19A 0.9800 .
C20 C25 1.385(3) .
C20 C21 1.386(3) .
C20 H20A 0.9300 .
C21 C22 1.378(3) .
C21 H21A 0.9300 .
C22 C23 1.374(3) .
C22 C26 1.524(3) .
C23 C24 1.378(3) .
C23 H23A 0.9300 .
C24 C25 1.385(3) .
C24 H24A 0.9300 .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
