#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:39:49 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257146 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038779.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_4038779
loop_
_publ_author_name
'Sun, Quan-Shun'
'Sun, Jing'
'Pan, Liu-Na'
'Yan, Chao-Guo'
_publ_section_title
;
 Selective Construction of Diverse Polycyclic Spirooxindoles via a
 Three-Component Reaction of Cyclic Mercapto-Substituted β-Enamino
 Esters, Isatins, and Cyclic 1,3-Diketones.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12117
_journal_page_last               12127
_journal_paper_doi               10.1021/acs.joc.0c01290
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C25 H20 N2 O4 S'
_chemical_formula_sum            'C25 H20 N2 O4 S'
_chemical_formula_weight         444.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.003(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2296(8)
_cell_length_b                   8.9965(5)
_cell_length_c                   20.0891(12)
_cell_measurement_reflns_used    5099
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.46
_cell_measurement_theta_min      2.48
_cell_volume                     2557.6(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20082
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.039
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0565
_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)+(0.0642P)²+0.6146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1448
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2959
_reflns_number_total             5015
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01290_si_002.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 4038776--4038786.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038779
_shelx_shelxl_version_number     2014/7
_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   0.963
_shelx_estimated_absorpt_t_max   0.972
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.54643(18) 0.1801(3) -0.11319(12) 0.0434(6) Uani 1 1 d . . . . .
C2 C 0.4913(2) 0.1809(3) -0.17414(14) 0.0605(8) Uani 1 1 d . . . . .
H2 H 0.4821 0.0937 -0.1988 0.073 Uiso 1 1 calc R U . . .
C3 C 0.4501(2) 0.3114(4) -0.19794(15) 0.0689(9) Uani 1 1 d . . . . .
H3 H 0.4135 0.3122 -0.2391 0.083 Uiso 1 1 calc R U . . .
C4 C 0.4624(2) 0.4413(4) -0.16150(15) 0.0631(8) Uani 1 1 d . . . . .
H4 H 0.4346 0.5290 -0.1781 0.076 Uiso 1 1 calc R U . . .
C5 C 0.51578(19) 0.4403(3) -0.10094(14) 0.0541(7) Uani 1 1 d . . . . .
H5 H 0.5233 0.5274 -0.0760 0.065 Uiso 1 1 calc R U . . .
C6 C 0.55899(18) 0.3100(3) -0.07612(12) 0.0433(6) Uani 1 1 d . . . . .
C7 C 0.63010(17) 0.1237(2) 0.02425(11) 0.0360(6) Uani 1 1 d . . . . .
H7 H 0.5680 0.1117 0.0405 0.043 Uiso 1 1 calc R U . . .
C8 C 0.63699(17) 0.0126(3) -0.03152(11) 0.0355(6) Uani 1 1 d . . . . .
C9 C 0.68017(17) -0.1251(3) -0.01866(11) 0.0368(6) Uani 1 1 d . . . . .
C10 C 0.6880(2) -0.2269(3) -0.07497(13) 0.0460(7) Uani 1 1 d . . . . .
C11 C 0.7592(2) -0.4437(3) -0.11310(16) 0.0774(10) Uani 1 1 d . . . . .
H11A H 0.7004 -0.4776 -0.1358 0.116 Uiso 1 1 calc R U . . .
H11B H 0.7955 -0.5275 -0.0956 0.116 Uiso 1 1 calc R U . . .
H11C H 0.7939 -0.3906 -0.1440 0.116 Uiso 1 1 calc R U . . .
C12 C 0.81088(19) 0.2912(3) 0.13093(12) 0.0420(6) Uani 1 1 d . . . . .
C13 C 0.8926(2) 0.3758(3) 0.14061(16) 0.0603(8) Uani 1 1 d . . . . .
H13 H 0.9023 0.4430 0.1759 0.072 Uiso 1 1 calc R U . . .
C14 C 0.9591(2) 0.3566(3) 0.0958(2) 0.0713(10) Uani 1 1 d . . . . .
H14 H 1.0138 0.4138 0.1010 0.086 Uiso 1 1 calc R U . . .
C15 C 0.9475(2) 0.2561(4) 0.04381(17) 0.0643(9) Uani 1 1 d . . . . .
C16 C 1.0212(3) 0.2396(5) -0.0055(2) 0.1079(14) Uani 1 1 d . . . . .
H16A H 1.0074 0.1528 -0.0326 0.162 Uiso 1 1 calc R U . . .
H16B H 1.0827 0.2297 0.0186 0.162 Uiso 1 1 calc R U . . .
H16C H 1.0199 0.3259 -0.0337 0.162 Uiso 1 1 calc R U . . .
C17 C 0.86532(19) 0.1693(3) 0.03628(14) 0.0484(7) Uani 1 1 d . . . . .
H17 H 0.8565 0.0996 0.0020 0.058 Uiso 1 1 calc R U . . .
C18 C 0.79789(17) 0.1877(2) 0.07970(11) 0.0350(6) Uani 1 1 d . . . . .
C19 C 0.70531(16) 0.1082(2) 0.08465(10) 0.0327(6) Uani 1 1 d . . . . .
C20 C 0.6682(2) 0.1887(3) 0.14505(12) 0.0415(6) Uani 1 1 d . . . . .
C21 C 0.72296(16) -0.0543(2) 0.09822(11) 0.0340(6) Uani 1 1 d . . . . .
C22 C 0.71517(16) -0.1592(2) 0.04987(11) 0.0353(6) Uani 1 1 d . . . . .
C23 C 0.7452(2) -0.3090(3) 0.07875(13) 0.0463(7) Uani 1 1 d . . . . .
H23A H 0.7961 -0.3503 0.0559 0.056 Uiso 1 1 calc R U . . .
H23B H 0.6926 -0.3781 0.0748 0.056 Uiso 1 1 calc R U . . .
C24 C 0.7785(2) -0.2779(3) 0.15212(13) 0.0504(7) Uani 1 1 d . . . . .
H24A H 0.7431 -0.3371 0.1812 0.060 Uiso 1 1 calc R U . . .
H24B H 0.8452 -0.3004 0.1618 0.060 Uiso 1 1 calc R U . . .
C25 C 0.76052(18) -0.1145(3) 0.16157(12) 0.0427(6) Uani 1 1 d . . . . .
N1 N 0.59254(15) 0.0478(2) -0.09194(9) 0.0463(6) Uani 1 1 d . . . . .
H1 H 0.5924 -0.0206 -0.1218 0.056 Uiso 1 1 calc R U . . .
N2 N 0.73344(16) 0.2910(2) 0.16794(10) 0.0461(6) Uani 1 1 d . . . . .
H2A H 0.7277 0.3490 0.2013 0.055 Uiso 1 1 calc R U . . .
O1 O 0.65311(18) -0.2073(2) -0.13143(10) 0.0814(7) Uani 1 1 d . . . . .
O2 O 0.74060(15) -0.3458(2) -0.05857(9) 0.0620(6) Uani 1 1 d . . . . .
O3 O 0.59249(15) 0.1660(2) 0.16581(9) 0.0596(5) Uani 1 1 d . . . . .
O4 O 0.77688(14) -0.04430(19) 0.21445(8) 0.0587(5) Uani 1 1 d . . . . .
S1 S 0.63905(6) 0.31506(7) -0.00440(3) 0.0571(3) Uani 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 0.0000 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
_geom_angle_publ_flag
C2 C1 C6 120.0(2) . . ?
C2 C1 N1 118.5(2) . . ?
C6 C1 N1 121.4(2) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 S1 120.19(19) . . ?
C5 C6 S1 120.0(2) . . ?
C8 C7 C19 115.54(19) . . ?
C8 C7 S1 112.20(16) . . ?
C19 C7 S1 105.58(15) . . ?
C8 C7 H7 107.7 . . ?
C19 C7 H7 107.7 . . ?
S1 C7 H7 107.7 . . ?
N1 C8 C9 122.1(2) . . ?
N1 C8 C7 116.9(2) . . ?
C9 C8 C7 120.7(2) . . ?
C8 C9 C22 117.7(2) . . ?
C8 C9 C10 118.6(2) . . ?
C22 C9 C10 123.7(2) . . ?
O1 C10 O2 121.2(2) . . ?
O1 C10 C9 125.3(2) . . ?
O2 C10 C9 113.4(2) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C18 121.2(3) . . ?
C13 C12 N2 128.7(2) . . ?
C18 C12 N2 110.1(2) . . ?
C14 C13 C12 117.4(3) . . ?
C14 C13 H13 121.3 . . ?
C12 C13 H13 121.3 . . ?
C15 C14 C13 122.6(3) . . ?
C15 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C14 C15 C17 118.7(3) . . ?
C14 C15 C16 121.4(3) . . ?
C17 C15 C16 119.9(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C15 119.7(3) . . ?
C18 C17 H17 120.2 . . ?
C15 C17 H17 120.2 . . ?
C17 C18 C12 120.3(2) . . ?
C17 C18 C19 131.1(2) . . ?
C12 C18 C19 108.6(2) . . ?
C21 C19 C18 109.96(19) . . ?
C21 C19 C7 108.67(18) . . ?
C18 C19 C7 116.42(18) . . ?
C21 C19 C20 112.07(18) . . ?
C18 C19 C20 101.61(19) . . ?
C7 C19 C20 108.01(19) . . ?
O3 C20 N2 126.9(2) . . ?
O3 C20 C19 125.3(2) . . ?
N2 C20 C19 107.8(2) . . ?
C22 C21 C25 111.7(2) . . ?
C22 C21 C19 123.3(2) . . ?
C25 C21 C19 124.6(2) . . ?
C21 C22 C9 122.1(2) . . ?
C21 C22 C23 110.4(2) . . ?
C9 C22 C23 127.5(2) . . ?
C22 C23 C24 104.70(19) . . ?
C22 C23 H23A 110.8 . . ?
C24 C23 H23A 110.8 . . ?
C22 C23 H23B 110.8 . . ?
C24 C23 H23B 110.8 . . ?
H23A C23 H23B 108.9 . . ?
C25 C24 C23 105.1(2) . . ?
C25 C24 H24A 110.7 . . ?
C23 C24 H24A 110.7 . . ?
C25 C24 H24B 110.7 . . ?
C23 C24 H24B 110.7 . . ?
H24A C24 H24B 108.8 . . ?
O4 C25 C21 126.0(2) . . ?
O4 C25 C24 125.9(2) . . ?
C21 C25 C24 108.0(2) . . ?
C8 N1 C1 129.3(2) . . ?
C8 N1 H1 115.3 . . ?
C1 N1 H1 115.3 . . ?
C20 N2 C12 111.9(2) . . ?
C20 N2 H2A 124.1 . . ?
C12 N2 H2A 124.1 . . ?
C10 O2 C11 116.4(2) . . ?
C6 S1 C7 100.08(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(4) . ?
C1 C6 1.387(3) . ?
C1 N1 1.404(3) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 S1 1.741(3) . ?
C7 C8 1.512(3) . ?
C7 C19 1.538(3) . ?
C7 S1 1.824(2) . ?
C7 H7 0.9800 . ?
C8 N1 1.346(3) . ?
C8 C9 1.395(3) . ?
C9 C22 1.447(3) . ?
C9 C10 1.468(3) . ?
C10 O1 1.203(3) . ?
C10 O2 1.327(3) . ?
C11 O2 1.451(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.386(4) . ?
C12 C18 1.386(3) . ?
C12 N2 1.392(3) . ?
C13 C14 1.383(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C17 1.401(4) . ?
C15 C16 1.524(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.372(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.511(3) . ?
C19 C21 1.504(3) . ?
C19 C20 1.552(3) . ?
C20 O3 1.213(3) . ?
C20 N2 1.353(3) . ?
C21 C22 1.350(3) . ?
C21 C25 1.434(3) . ?
C22 C23 1.512(3) . ?
C23 C24 1.526(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.507(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O4 1.237(3) . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?
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
N1 H1 O1 0.86 1.91 2.604(3) 137.1 .
N2 H2A O4 0.86 1.95 2.806(3) 171.3 2_655
