#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:39:49 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257146 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038781.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_4038781
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         'C28 H19 Cl N2 O6 S'
_chemical_formula_sum            'C28 H19 Cl N2 O6 S'
_chemical_formula_weight         546.96
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.027(4)
_cell_angle_beta                 114.297(4)
_cell_angle_gamma                94.437(4)
_cell_formula_units_Z            2
_cell_length_a                   10.2791(13)
_cell_length_b                   11.3288(14)
_cell_length_c                   11.7187(15)
_cell_measurement_reflns_used    9048
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.23
_cell_volume                     1239.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_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  0.0302
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17676
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_min         2.672
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0457
_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)+(0.0576P)²+0.7410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1218
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3955
_reflns_number_total             4836
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01290_si_002.cif
_cod_data_source_block           4c
_cod_depositor_comments
'Adding full bibliography for 4038776--4038786.cif.'
_cod_database_code               4038781
_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   0.929
_shelx_estimated_absorpt_t_max   0.945
loop_
_space_group_symop_operation_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1053(2) 0.87160(18) 0.9133(2) 0.0380(5) Uani 1 1 d . . . . .
C2 C 0.0271(3) 0.8498(2) 0.9850(3) 0.0561(7) Uani 1 1 d . . . . .
H2 H 0.0748 0.8473 1.0717 0.067 Uiso 1 1 calc R U . . .
C3 C -0.1189(3) 0.8323(3) 0.9295(4) 0.0725(9) Uani 1 1 d . . . . .
H3 H -0.1704 0.8183 0.9781 0.087 Uiso 1 1 calc R U . . .
C4 C -0.1893(3) 0.8352(3) 0.8014(4) 0.0716(9) Uani 1 1 d . . . . .
H4 H -0.2887 0.8228 0.7635 0.086 Uiso 1 1 calc R U . . .
C5 C -0.1138(3) 0.8566(2) 0.7279(3) 0.0562(7) Uani 1 1 d . . . . .
H5 H -0.1629 0.8585 0.6413 0.067 Uiso 1 1 calc R U . . .
C6 C 0.0352(2) 0.87515(18) 0.7828(2) 0.0377(5) Uani 1 1 d . . . . .
C7 C 0.3458(2) 0.87038(16) 0.86871(17) 0.0262(4) Uani 1 1 d . . . . .
H7 H 0.4435 0.9080 0.8965 0.031 Uiso 1 1 calc R U . . .
C8 C 0.2538(2) 0.93596(16) 0.75256(17) 0.0280(4) Uani 1 1 d . . . . .
C9 C 0.2768(2) 1.07021(17) 0.77910(19) 0.0350(5) Uani 1 1 d . . . . .
H9A H 0.2503 1.0878 0.8473 0.042 Uiso 1 1 calc R U . . .
H9B H 0.3781 1.0945 0.8070 0.042 Uiso 1 1 calc R U . . .
C10 C 0.1940(2) 1.14284(18) 0.6695(2) 0.0399(5) Uani 1 1 d . . . . .
C11 C 0.1604(4) 1.3378(2) 0.6017(3) 0.0912(12) Uani 1 1 d . . . . .
H11A H 0.1825 1.3285 0.5303 0.137 Uiso 1 1 calc R U . . .
H11B H 0.1891 1.4175 0.6354 0.137 Uiso 1 1 calc R U . . .
H11C H 0.0592 1.3216 0.5766 0.137 Uiso 1 1 calc R U . . .
C12 C 0.2980(2) 0.58480(18) 0.9565(2) 0.0367(5) Uani 1 1 d . . . . .
C13 C 0.2190(3) 0.4950(2) 0.9853(3) 0.0539(6) Uani 1 1 d . . . . .
H13 H 0.2590 0.4544 1.0591 0.065 Uiso 1 1 calc R U . . .
C14 C 0.0797(3) 0.4674(2) 0.9018(3) 0.0640(8) Uani 1 1 d . . . . .
H14 H 0.0235 0.4080 0.9192 0.077 Uiso 1 1 calc R U . . .
C15 C 0.0228(3) 0.5276(2) 0.7919(3) 0.0585(7) Uani 1 1 d . . . . .
C16 C 0.1017(2) 0.61822(18) 0.7621(2) 0.0408(5) Uani 1 1 d . . . . .
H16 H 0.0624 0.6572 0.6872 0.049 Uiso 1 1 calc R U . . .
C17 C 0.2394(2) 0.64778(17) 0.84719(18) 0.0312(4) Uani 1 1 d . . . . .
C18 C 0.35488(19) 0.73717(16) 0.84243(17) 0.0263(4) Uani 1 1 d . . . . .
C19 C 0.4887(2) 0.70365(17) 0.95906(17) 0.0302(4) Uani 1 1 d . . . . .
C20 C 0.4324(2) 0.62216(17) 0.70050(18) 0.0320(4) Uani 1 1 d . . . . .
C21 C 0.3777(2) 0.72875(16) 0.72411(17) 0.0268(4) Uani 1 1 d . . . . .
C22 C 0.3509(2) 0.81640(16) 0.64131(17) 0.0284(4) Uani 1 1 d . . . . .
C23 C 0.3763(2) 0.80613(17) 0.52935(18) 0.0314(4) Uani 1 1 d . . . . .
C24 C 0.3476(3) 0.8923(2) 0.4388(2) 0.0446(5) Uani 1 1 d . . . . .
H24 H 0.3098 0.9616 0.4489 0.054 Uiso 1 1 calc R U . . .
C25 C 0.3751(3) 0.8751(2) 0.3350(2) 0.0534(6) Uani 1 1 d . . . . .
H25 H 0.3562 0.9326 0.2750 0.064 Uiso 1 1 calc R U . . .
C26 C 0.4309(3) 0.7717(2) 0.3199(2) 0.0517(6) Uani 1 1 d . . . . .
H26 H 0.4485 0.7603 0.2491 0.062 Uiso 1 1 calc R U . . .
C27 C 0.4607(3) 0.6861(2) 0.4077(2) 0.0445(5) Uani 1 1 d . . . . .
H27 H 0.4992 0.6173 0.3975 0.053 Uiso 1 1 calc R U . . .
C28 C 0.4322(2) 0.70404(18) 0.51145(18) 0.0337(4) Uani 1 1 d . . . . .
Cl1 Cl -0.15332(9) 0.48980(9) 0.68621(11) 0.1077(4) Uani 1 1 d . . . . .
N1 N 0.10763(17) 0.88762(15) 0.70467(15) 0.0345(4) Uani 1 1 d . . . . .
H1 H 0.0638 0.8660 0.6268 0.041 Uiso 1 1 calc R U . . .
N2 N 0.44262(19) 0.62320(16) 1.02241(16) 0.0376(4) Uani 1 1 d . . . . .
H2A H 0.4961 0.5986 1.0948 0.045 Uiso 1 1 calc R U . . .
O1 O 0.1052(2) 1.10691(16) 0.57169(18) 0.0774(7) Uani 1 1 d . . . . .
O2 O 0.2363(2) 1.25629(14) 0.69595(17) 0.0680(6) Uani 1 1 d . . . . .
O3 O 0.60910(15) 0.74842(14) 0.98818(14) 0.0417(4) Uani 1 1 d . . . . .
O4 O 0.45910(17) 0.61463(12) 0.59550(13) 0.0395(4) Uani 1 1 d . . . . .
O5 O 0.45700(18) 0.53748(13) 0.76690(14) 0.0430(4) Uani 1 1 d . . . . .
O6 O 0.30194(15) 0.92017(12) 0.65394(12) 0.0335(3) Uani 1 1 d . . . . .
S1 S 0.29299(6) 0.89526(5) 0.99453(5) 0.03645(16) 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'
Cl Cl 0.1484 0.1585 '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 120.3(2) . . ?
C2 C1 S1 117.0(2) . . ?
C6 C1 S1 122.67(16) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.1(2) . . ?
C5 C6 N1 118.5(2) . . ?
C1 C6 N1 123.20(18) . . ?
C8 C7 C18 114.09(15) . . ?
C8 C7 S1 110.45(13) . . ?
C18 C7 S1 113.57(12) . . ?
C8 C7 H7 106.0 . . ?
C18 C7 H7 106.0 . . ?
S1 C7 H7 106.0 . . ?
N1 C8 O6 106.74(15) . . ?
N1 C8 C9 115.02(16) . . ?
O6 C8 C9 103.54(15) . . ?
N1 C8 C7 110.38(15) . . ?
O6 C8 C7 109.98(14) . . ?
C9 C8 C7 110.82(15) . . ?
C10 C9 C8 114.89(17) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
O1 C10 O2 123.0(2) . . ?
O1 C10 C9 126.7(2) . . ?
O2 C10 C9 110.19(19) . . ?
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 C17 121.9(2) . . ?
C13 C12 N2 128.2(2) . . ?
C17 C12 N2 109.83(17) . . ?
C14 C13 C12 118.0(2) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 122.2(2) . . ?
C14 C15 Cl1 119.4(2) . . ?
C16 C15 Cl1 118.4(2) . . ?
C17 C16 C15 117.5(2) . . ?
C17 C16 H16 121.3 . . ?
C15 C16 H16 121.3 . . ?
C16 C17 C12 120.21(19) . . ?
C16 C17 C18 131.09(18) . . ?
C12 C17 C18 108.53(17) . . ?
C21 C18 C17 114.14(16) . . ?
C21 C18 C7 107.47(14) . . ?
C17 C18 C7 118.18(15) . . ?
C21 C18 C19 111.66(15) . . ?
C17 C18 C19 101.24(15) . . ?
C7 C18 C19 103.46(14) . . ?
O3 C19 N2 127.76(18) . . ?
O3 C19 C18 124.51(18) . . ?
N2 C19 C18 107.61(17) . . ?
O5 C20 O4 116.67(17) . . ?
O5 C20 C21 124.89(18) . . ?
O4 C20 C21 118.44(16) . . ?
C22 C21 C20 119.56(17) . . ?
C22 C21 C18 122.88(17) . . ?
C20 C21 C18 117.56(16) . . ?
O6 C22 C21 125.00(17) . . ?
O6 C22 C23 113.57(16) . . ?
C21 C22 C23 121.43(17) . . ?
C28 C23 C24 118.44(18) . . ?
C28 C23 C22 117.40(17) . . ?
C24 C23 C22 124.16(18) . . ?
C25 C24 C23 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.9(2) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 121.0(2) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 118.6(2) . . ?
C26 C27 H27 120.7 . . ?
C28 C27 H27 120.7 . . ?
O4 C28 C27 117.03(18) . . ?
O4 C28 C23 121.19(17) . . ?
C27 C28 C23 121.77(19) . . ?
C6 N1 C8 120.88(16) . . ?
C6 N1 H1 119.6 . . ?
C8 N1 H1 119.6 . . ?
C19 N2 C12 112.09(16) . . ?
C19 N2 H2A 124.0 . . ?
C12 N2 H2A 124.0 . . ?
C10 O2 C11 116.5(2) . . ?
C20 O4 C28 121.96(15) . . ?
C22 O6 C8 119.23(14) . . ?
C1 S1 C7 100.11(10) . . ?
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 1.393(3) . ?
C1 C6 1.398(3) . ?
C1 S1 1.763(2) . ?
C2 C3 1.366(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.399(3) . ?
C7 C8 1.533(3) . ?
C7 C18 1.558(3) . ?
C7 S1 1.7975(18) . ?
C7 H7 0.9800 . ?
C8 N1 1.432(2) . ?
C8 O6 1.448(2) . ?
C8 C9 1.533(3) . ?
C9 C10 1.504(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O1 1.180(3) . ?
C10 O2 1.319(3) . ?
C11 O2 1.444(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.381(3) . ?
C12 C17 1.395(3) . ?
C12 N2 1.396(3) . ?
C13 C14 1.372(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(3) . ?
C15 Cl1 1.741(3) . ?
C16 C17 1.369(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.518(3) . ?
C18 C21 1.503(3) . ?
C18 C19 1.562(3) . ?
C19 O3 1.208(2) . ?
C19 N2 1.353(3) . ?
C20 O5 1.211(2) . ?
C20 O4 1.370(2) . ?
C20 C21 1.443(3) . ?
C21 C22 1.352(3) . ?
C22 O6 1.345(2) . ?
C22 C23 1.446(3) . ?
C23 C28 1.383(3) . ?
C23 C24 1.398(3) . ?
C24 C25 1.374(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.372(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.382(3) . ?
C27 H27 0.9300 . ?
C28 O4 1.376(2) . ?
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 2.30 3.077(2) 150.7 2_576
N2 H2A O5 0.86 2.17 2.945(2) 149.7 2_667
