#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:22:37 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266146 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/05/7060515.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_7060515
loop_
_publ_author_name
'Pan, Liu-Na'
'Wang, Qing'
'Sun, Jing'
'Sun, Quan-Shun'
'Yan, Chao-Guo'
_publ_section_title
;
 Molecular diversity of the acid promoted domino reaction of
 3-hydroxy-3-(indol-3-yl)indolin-2-ones and cyclic mercapto-substituted
 β-enamino esters
;
_journal_issue                   18
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8314
_journal_page_last               8320
_journal_paper_doi               10.1039/D1NJ00947H
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         ' C27 H21 N3 O3 S, C2 H6 O S '
_chemical_formula_sum            'C29 H27 N3 O4 S2'
_chemical_formula_weight         545.65
_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
_audit_update_record
;
2020-12-29 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                88.6303(15)
_cell_angle_beta                 73.6805(14)
_cell_angle_gamma                69.6071(14)
_cell_formula_units_Z            2
_cell_length_a                   11.2427(5)
_cell_length_b                   11.4819(5)
_cell_length_c                   13.5468(6)
_cell_measurement_reflns_used    9593
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.36
_cell_volume                     1567.75(12)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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  0.0312
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22380
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.226
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0440
_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)+(0.0533P)²+0.4549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4676
_reflns_number_total             6105
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj00947h2.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 7060515--7060528.cif.'
_cod_database_code               7060515
_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   0.953
_shelx_estimated_absorpt_t_max   0.960
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 -0.11099(17) 0.67671(17) 0.48475(15) 0.0398(4) Uani 1 1 d . . . . .
C2 C -0.22680(19) 0.7354(2) 0.56292(17) 0.0545(5) Uani 1 1 d . . . . .
H2 H -0.2227 0.7657 0.6245 0.065 Uiso 1 1 calc R U . . .
C3 C -0.3478(2) 0.7490(2) 0.5499(2) 0.0688(7) Uani 1 1 d . . . . .
H3 H -0.4251 0.7871 0.6032 0.083 Uiso 1 1 calc R U . . .
C4 C -0.3553(2) 0.7068(2) 0.4588(2) 0.0720(7) Uani 1 1 d . . . . .
H4 H -0.4374 0.7167 0.4502 0.086 Uiso 1 1 calc R U . . .
C5 C -0.2410(2) 0.6495(2) 0.38010(19) 0.0578(6) Uani 1 1 d . . . . .
H5 H -0.2461 0.6221 0.3179 0.069 Uiso 1 1 calc R U . . .
C6 C -0.11812(18) 0.63260(17) 0.39302(15) 0.0422(4) Uani 1 1 d . . . . .
C7 C 0.13460(17) 0.63144(16) 0.31439(13) 0.0342(4) Uani 1 1 d . . . . .
H7 H 0.2254 0.5765 0.2790 0.041 Uiso 1 1 calc R U . . .
C8 C 0.12895(16) 0.64281(15) 0.42650(13) 0.0330(4) Uani 1 1 d . . . . .
C9 C 0.23970(18) 0.63313(17) 0.45182(14) 0.0400(4) Uani 1 1 d . . . . .
H9 H 0.3175 0.6199 0.3987 0.048 Uiso 1 1 calc R U . . .
C10 C 0.24422(19) 0.64210(18) 0.55591(15) 0.0413(4) Uani 1 1 d . . . . .
C11 C 0.3877(3) 0.6143(3) 0.66021(19) 0.0722(7) Uani 1 1 d . . . . .
H11A H 0.3357 0.6927 0.7000 0.108 Uiso 1 1 calc R U . . .
H11B H 0.4798 0.5961 0.6536 0.108 Uiso 1 1 calc R U . . .
H11C H 0.3605 0.5496 0.6943 0.108 Uiso 1 1 calc R U . . .
C12 C -0.09879(19) 0.88377(17) 0.25379(14) 0.0415(4) Uani 1 1 d . . . . .
C13 C -0.2270(2) 0.9691(2) 0.28588(18) 0.0556(5) Uani 1 1 d . . . . .
H13 H -0.2838 0.9827 0.2449 0.067 Uiso 1 1 calc R U . . .
C14 C -0.2670(2) 1.0331(2) 0.3813(2) 0.0641(6) Uani 1 1 d . . . . .
H14 H -0.3529 1.0907 0.4052 0.077 Uiso 1 1 calc R U . . .
C15 C -0.1836(2) 1.01422(19) 0.44219(18) 0.0564(6) Uani 1 1 d . . . . .
H15 H -0.2127 1.0605 0.5054 0.068 Uiso 1 1 calc R U . . .
C16 C -0.05661(19) 0.92668(17) 0.40976(15) 0.0436(5) Uani 1 1 d . . . . .
H16 H -0.0003 0.9128 0.4511 0.052 Uiso 1 1 calc R U . . .
C17 C -0.01459(17) 0.86019(15) 0.31518(13) 0.0344(4) Uani 1 1 d . . . . .
C18 C 0.11462(17) 0.75755(16) 0.26062(13) 0.0340(4) Uani 1 1 d . . . . .
C19 C 0.09066(19) 0.73533(18) 0.15585(14) 0.0417(4) Uani 1 1 d . . . . .
C20 C 0.2361(2) 0.90621(19) 0.27257(15) 0.0473(5) Uani 1 1 d . . . . .
H20 H 0.1607 0.9743 0.3045 0.057 Uiso 1 1 calc R U . . .
C21 C 0.23553(18) 0.79348(17) 0.24328(13) 0.0368(4) Uani 1 1 d . . . . .
C22 C 0.37279(18) 0.71754(17) 0.19547(13) 0.0389(4) Uani 1 1 d . . . . .
C23 C 0.44046(19) 0.59723(19) 0.14584(14) 0.0465(5) Uani 1 1 d . . . . .
H23 H 0.3939 0.5466 0.1386 0.056 Uiso 1 1 calc R U . . .
C24 C 0.5769(2) 0.5547(2) 0.10787(17) 0.0577(6) Uani 1 1 d . . . . .
H24 H 0.6221 0.4744 0.0758 0.069 Uiso 1 1 calc R U . . .
C25 C 0.6480(2) 0.6295(3) 0.11656(18) 0.0658(7) Uani 1 1 d . . . . .
H25 H 0.7400 0.5981 0.0907 0.079 Uiso 1 1 calc R U . . .
C26 C 0.5858(2) 0.7480(3) 0.16227(19) 0.0635(6) Uani 1 1 d . . . . .
H26 H 0.6337 0.7984 0.1671 0.076 Uiso 1 1 calc R U . . .
C27 C 0.4483(2) 0.7910(2) 0.20151(15) 0.0477(5) Uani 1 1 d . . . . .
C28 C 0.0283(4) 0.8625(3) 0.8581(3) 0.1104(12) Uani 1 1 d . . . . .
H28A H -0.0184 0.9510 0.8648 0.166 Uiso 1 1 calc R U . . .
H28B H 0.0813 0.8363 0.7879 0.166 Uiso 1 1 calc R U . . .
H28C H 0.0848 0.8422 0.9025 0.166 Uiso 1 1 calc R U . . .
C29 C 0.0294(3) 0.6340(3) 0.8890(2) 0.0895(9) Uani 1 1 d . . . . .
H29A H 0.0804 0.6333 0.9354 0.134 Uiso 1 1 calc R U . . .
H29B H 0.0876 0.6091 0.8200 0.134 Uiso 1 1 calc R U . . .
H29C H -0.0168 0.5770 0.9093 0.134 Uiso 1 1 calc R U . . .
N1 N 0.01104(14) 0.66354(14) 0.49949(11) 0.0405(4) Uani 1 1 d . . . . .
H1 H 0.0116 0.6693 0.5625 0.049 Uiso 1 1 calc R U . . .
N2 N -0.03369(16) 0.81049(16) 0.16017(12) 0.0475(4) Uani 1 1 d . . . . .
H2A H -0.0688 0.8130 0.1110 0.057 Uiso 1 1 calc R U . . .
N3 N 0.36298(18) 0.90508(17) 0.24850(15) 0.0577(5) Uani 1 1 d . . . . .
H3A H 0.3854 0.9663 0.2609 0.069 Uiso 1 1 calc R U . . .
O1 O 0.15071(14) 0.66445(14) 0.63377(10) 0.0523(4) Uani 1 1 d . . . . .
O2 O 0.36843(14) 0.62105(15) 0.55982(11) 0.0572(4) Uani 1 1 d . . . . .
O3 O 0.17033(14) 0.66305(15) 0.08384(10) 0.0607(4) Uani 1 1 d . . . . .
O4 O -0.15909(16) 0.82805(19) 1.00500(12) 0.0774(5) Uani 1 1 d . . . . .
S1 S 0.02891(5) 0.54936(4) 0.29734(4) 0.04621(14) Uani 1 1 d . . . . .
S2 S -0.08642(7) 0.78579(7) 0.89345(4) 0.06989(19) 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 119.44(18) . . ?
C2 C1 N1 119.45(18) . . ?
C6 C1 N1 121.11(16) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.64(19) . . ?
C1 C6 S1 119.37(14) . . ?
C5 C6 S1 120.92(17) . . ?
C8 C7 C18 114.23(13) . . ?
C8 C7 S1 110.71(12) . . ?
C18 C7 S1 114.50(12) . . ?
C8 C7 H7 105.5 . . ?
C18 C7 H7 105.5 . . ?
S1 C7 H7 105.5 . . ?
C9 C8 N1 121.77(16) . . ?
C9 C8 C7 119.68(15) . . ?
N1 C8 C7 118.54(15) . . ?
C8 C9 C10 123.72(17) . . ?
C8 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
O1 C10 O2 121.91(17) . . ?
O1 C10 C9 126.43(17) . . ?
O2 C10 C9 111.66(16) . . ?
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 122.02(18) . . ?
C13 C12 N2 128.16(18) . . ?
C17 C12 N2 109.82(16) . . ?
C14 C13 C12 117.0(2) . . ?
C14 C13 H13 121.5 . . ?
C12 C13 H13 121.5 . . ?
C15 C14 C13 122.0(2) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.06(19) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C12 119.69(17) . . ?
C16 C17 C18 131.41(16) . . ?
C12 C17 C18 108.89(15) . . ?
C21 C18 C17 114.12(14) . . ?
C21 C18 C19 110.75(14) . . ?
C17 C18 C19 101.26(14) . . ?
C21 C18 C7 110.58(14) . . ?
C17 C18 C7 112.77(14) . . ?
C19 C18 C7 106.74(13) . . ?
O3 C19 N2 126.59(17) . . ?
O3 C19 C18 125.69(17) . . ?
N2 C19 C18 107.72(15) . . ?
C21 C20 N3 110.54(18) . . ?
C21 C20 H20 124.7 . . ?
N3 C20 H20 124.7 . . ?
C20 C21 C22 105.84(16) . . ?
C20 C21 C18 125.99(16) . . ?
C22 C21 C18 128.15(16) . . ?
C23 C22 C27 117.79(17) . . ?
C23 C22 C21 135.53(18) . . ?
C27 C22 C21 106.65(17) . . ?
C24 C23 C22 119.2(2) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 121.2(2) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 121.4(2) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C27 117.6(2) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
N3 C27 C26 129.3(2) . . ?
N3 C27 C22 108.03(17) . . ?
C26 C27 C22 122.7(2) . . ?
S2 C28 H28A 109.5 . . ?
S2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
S2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
S2 C29 H29A 109.5 . . ?
S2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
S2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C8 N1 C1 128.01(16) . . ?
C8 N1 H1 116.0 . . ?
C1 N1 H1 116.0 . . ?
C19 N2 C12 112.17(15) . . ?
C19 N2 H2A 123.9 . . ?
C12 N2 H2A 123.9 . . ?
C27 N3 C20 108.92(17) . . ?
C27 N3 H3A 125.5 . . ?
C20 N3 H3A 125.5 . . ?
C10 O2 C11 116.66(17) . . ?
C6 S1 C7 99.96(8) . . ?
O4 S2 C28 105.33(14) . . ?
O4 S2 C29 107.14(12) . . ?
C28 S2 C29 97.19(17) . . ?
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 1.385(3) . ?
C1 C6 1.386(3) . ?
C1 N1 1.397(2) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 S1 1.755(2) . ?
C7 C8 1.509(2) . ?
C7 C18 1.579(2) . ?
C7 S1 1.8160(17) . ?
C7 H7 0.9800 . ?
C8 C9 1.350(2) . ?
C8 N1 1.359(2) . ?
C9 C10 1.433(3) . ?
C9 H9 0.9300 . ?
C10 O1 1.219(2) . ?
C10 O2 1.348(2) . ?
C11 O2 1.432(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.383(3) . ?
C12 C17 1.384(3) . ?
C12 N2 1.397(2) . ?
C13 C14 1.379(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.513(2) . ?
C18 C21 1.510(2) . ?
C18 C19 1.560(2) . ?
C19 O3 1.213(2) . ?
C19 N2 1.348(2) . ?
C20 C21 1.366(3) . ?
C20 N3 1.366(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.445(3) . ?
C22 C23 1.401(3) . ?
C22 C27 1.407(3) . ?
C23 C24 1.380(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.388(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.364(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.392(3) . ?
C26 H26 0.9300 . ?
C27 N3 1.364(3) . ?
C28 S2 1.759(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 S2 1.766(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?
N3 H3A 0.8600 . ?
O4 S2 1.5004(16) . ?
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 2.04 2.719(2) 135.1 .
N2 H2A O4 0.86 1.95 2.810(2) 176.1 1_554
