#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:22:37 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266146 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/05/7060519.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_7060519
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         'C34 H26 Cl N3 O3 S'
_chemical_formula_sum            'C34 H26 Cl N3 O3 S'
_chemical_formula_weight         592.09
_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
_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                90
_cell_angle_beta                 110.707(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.0749(18)
_cell_length_b                   11.6066(11)
_cell_length_c                   16.6701(16)
_cell_measurement_reflns_used    5395
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.95
_cell_measurement_theta_min      2.19
_cell_volume                     3452.3(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(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  0.0997
_diffrn_reflns_av_unetI/netI     0.1081
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31809
_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         26.000
_diffrn_reflns_theta_min         2.093
_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    1.139
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         6771
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1693
_refine_ls_R_factor_gt           0.0777
_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)+(0.1253P)²+1.1317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2001
_refine_ls_wR_factor_ref         0.2471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3363
_reflns_number_total             6771
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj00947h2.cif
_cod_data_source_block           3g
_cod_depositor_comments
'Adding full bibliography for 7060515--7060528.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7060519
_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   0.952
_shelx_estimated_absorpt_t_max   0.960
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
C1 C 0.1807(2) 0.3422(5) 0.3126(3) 0.0571(13) Uani 1 1 d . . . . .
C2 C 0.1073(3) 0.3712(6) 0.2623(3) 0.0752(16) Uani 1 1 d . . . . .
H2 H 0.0957 0.4459 0.2417 0.090 Uiso 1 1 calc R U . . .
C3 C 0.0522(3) 0.2881(7) 0.2432(4) 0.093(2) Uani 1 1 d . . . . .
H3 H 0.0028 0.3074 0.2113 0.112 Uiso 1 1 calc R U . . .
C4 C 0.0701(3) 0.1764(7) 0.2713(4) 0.087(2) Uani 1 1 d . . . . .
H4 H 0.0326 0.1208 0.2576 0.105 Uiso 1 1 calc R U . . .
C5 C 0.1432(3) 0.1458(5) 0.3197(3) 0.0728(16) Uani 1 1 d . . . . .
H5 H 0.1549 0.0701 0.3376 0.087 Uiso 1 1 calc R U . . .
C6 C 0.1983(2) 0.2290(5) 0.3408(3) 0.0536(12) Uani 1 1 d . . . . .
C7 C 0.3321(2) 0.3672(3) 0.3507(2) 0.0367(10) Uani 1 1 d . . . . .
H7 H 0.3749 0.4144 0.3847 0.044 Uiso 1 1 calc R U . . .
C8 C 0.3366(2) 0.2587(3) 0.4027(3) 0.0398(10) Uani 1 1 d . . . . .
C9 C 0.4033(2) 0.2231(3) 0.4590(3) 0.0402(10) Uani 1 1 d . . . . .
H9 H 0.4461 0.2651 0.4637 0.048 Uiso 1 1 calc R U . . .
C10 C 0.4107(2) 0.1219(4) 0.5125(3) 0.0465(11) Uani 1 1 d . . . . .
C11 C 0.4933(3) 0.0070(4) 0.6214(3) 0.0715(15) Uani 1 1 d . . . . .
H11A H 0.4661 0.0183 0.6593 0.107 Uiso 1 1 calc R U . . .
H11B H 0.5458 0.0000 0.6543 0.107 Uiso 1 1 calc R U . . .
H11C H 0.4761 -0.0619 0.5885 0.107 Uiso 1 1 calc R U . . .
C12 C 0.0990(3) 0.5850(5) 0.0079(3) 0.0721(14) Uani 1 1 d . U . . .
H12 H 0.0979 0.5445 -0.0407 0.086 Uiso 1 1 calc R U . . .
C13 C 0.0347(3) 0.6388(6) 0.0107(4) 0.0898(17) Uani 1 1 d . U . . .
H13 H -0.0096 0.6339 -0.0364 0.108 Uiso 1 1 calc R U . . .
C14 C 0.0358(3) 0.6988(5) 0.0822(4) 0.0817(16) Uani 1 1 d . U . . .
H14 H -0.0069 0.7374 0.0824 0.098 Uiso 1 1 calc R U . . .
C15 C 0.0983(3) 0.7013(5) 0.1512(4) 0.0723(14) Uani 1 1 d . U . . .
H15 H 0.0983 0.7382 0.2007 0.087 Uiso 1 1 calc R U . . .
C16 C 0.1633(3) 0.6496(4) 0.1499(3) 0.0618(13) Uani 1 1 d . U . . .
H16 H 0.2066 0.6536 0.1983 0.074 Uiso 1 1 calc R U . . .
C17 C 0.1651(2) 0.5927(4) 0.0788(3) 0.0486(11) Uani 1 1 d . U . . .
C18 C 0.2370(2) 0.5405(4) 0.0755(3) 0.0499(12) Uani 1 1 d . . . . .
H18A H 0.2274 0.5087 0.0188 0.060 Uiso 1 1 calc R U . . .
H18B H 0.2742 0.6010 0.0847 0.060 Uiso 1 1 calc R U . . .
C19 C 0.2415(2) 0.3357(4) 0.1312(3) 0.0414(10) Uani 1 1 d . . . . .
C20 C 0.1825(2) 0.2885(4) 0.0637(3) 0.0589(13) Uani 1 1 d . . . . .
H20 H 0.1547 0.3326 0.0166 0.071 Uiso 1 1 calc R U . . .
C21 C 0.1669(3) 0.1734(5) 0.0698(3) 0.0658(14) Uani 1 1 d . . . . .
H21 H 0.1275 0.1388 0.0265 0.079 Uiso 1 1 calc R U . . .
C22 C 0.2095(2) 0.1093(4) 0.1398(3) 0.0537(12) Uani 1 1 d . . . . .
C23 C 0.2694(2) 0.1561(4) 0.2054(3) 0.0430(11) Uani 1 1 d . . . . .
H23 H 0.2987 0.1111 0.2511 0.052 Uiso 1 1 calc R U . . .
C24 C 0.2842(2) 0.2712(3) 0.2007(3) 0.0362(10) Uani 1 1 d . . . . .
C25 C 0.34242(19) 0.3480(3) 0.2619(2) 0.0340(9) Uani 1 1 d . . . . .
C26 C 0.3255(2) 0.4652(4) 0.2140(3) 0.0355(10) Uani 1 1 d . . . . .
C27 C 0.4421(2) 0.2223(3) 0.2347(3) 0.0399(10) Uani 1 1 d . . . . .
H27 H 0.4087 0.1714 0.1972 0.048 Uiso 1 1 calc R U . . .
C28 C 0.4223(2) 0.3133(3) 0.2746(3) 0.0361(10) Uani 1 1 d . . . . .
C29 C 0.49150(19) 0.3702(3) 0.3267(2) 0.0326(9) Uani 1 1 d . . . . .
C30 C 0.5101(2) 0.4664(3) 0.3796(3) 0.0404(10) Uani 1 1 d . . . . .
H30 H 0.4729 0.5108 0.3886 0.048 Uiso 1 1 calc R U . . .
C31 C 0.5842(2) 0.4946(4) 0.4183(3) 0.0526(12) Uani 1 1 d . . . . .
H31 H 0.5970 0.5580 0.4548 0.063 Uiso 1 1 calc R U . . .
C32 C 0.6413(2) 0.4307(5) 0.4045(3) 0.0586(13) Uani 1 1 d . . . . .
H32 H 0.6910 0.4531 0.4310 0.070 Uiso 1 1 calc R U . . .
C33 C 0.6252(2) 0.3377(4) 0.3536(3) 0.0521(12) Uani 1 1 d . . . . .
H33 H 0.6630 0.2950 0.3445 0.062 Uiso 1 1 calc R U . . .
C34 C 0.5496(2) 0.3067(3) 0.3146(3) 0.0395(10) Uani 1 1 d . . . . .
Cl1 Cl 0.18480(8) -0.03408(11) 0.14711(11) 0.0838(5) Uani 1 1 d . . . . .
N1 N 0.27191(17) 0.2007(3) 0.3915(2) 0.0518(10) Uani 1 1 d . . . . .
H1 H 0.2770 0.1373 0.4197 0.062 Uiso 1 1 calc R U . . .
N2 N 0.26743(17) 0.4500(3) 0.1393(2) 0.0393(8) Uani 1 1 d . . . . .
N3 N 0.51852(18) 0.2178(3) 0.2584(2) 0.0480(9) Uani 1 1 d . . . . .
H3A H 0.5431 0.1676 0.2410 0.058 Uiso 1 1 calc R U . . .
O1 O 0.35971(18) 0.0579(3) 0.5115(2) 0.0666(10) Uani 1 1 d . . . . .
O2 O 0.48139(17) 0.1046(3) 0.5641(2) 0.0598(9) Uani 1 1 d . . . . .
O3 O 0.35901(14) 0.5557(2) 0.23845(19) 0.0473(8) Uani 1 1 d . . . . .
S1 S 0.24941(6) 0.45012(10) 0.34389(8) 0.0537(4) 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 120.0(5) . . ?
C2 C1 S1 119.5(4) . . ?
C6 C1 S1 120.4(3) . . ?
C3 C2 C1 119.5(6) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.1(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 121.0(5) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 119.3(6) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 N1 120.2(5) . . ?
C1 C6 N1 119.7(4) . . ?
C8 C7 C25 114.8(3) . . ?
C8 C7 S1 110.4(3) . . ?
C25 C7 S1 114.2(2) . . ?
C8 C7 H7 105.5 . . ?
C25 C7 H7 105.5 . . ?
S1 C7 H7 105.5 . . ?
C9 C8 N1 122.0(4) . . ?
C9 C8 C7 120.0(3) . . ?
N1 C8 C7 118.0(3) . . ?
C8 C9 C10 122.5(4) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
O1 C10 O2 122.4(4) . . ?
O1 C10 C9 125.5(4) . . ?
O2 C10 C9 112.0(4) . . ?
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 119.1(5) . . ?
C13 C12 H12 120.4 . . ?
C17 C12 H12 120.4 . . ?
C14 C13 C12 120.9(5) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 119.6(5) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.7(6) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 121.3(5) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C12 118.3(4) . . ?
C16 C17 C18 121.6(4) . . ?
C12 C17 C18 120.1(5) . . ?
N2 C18 C17 113.1(3) . . ?
N2 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
N2 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C24 C19 C20 122.3(4) . . ?
C24 C19 N2 110.4(3) . . ?
C20 C19 N2 127.3(4) . . ?
C21 C20 C19 117.0(4) . . ?
C21 C20 H20 121.5 . . ?
C19 C20 H20 121.5 . . ?
C22 C21 C20 120.5(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 122.1(4) . . ?
C21 C22 Cl1 118.7(4) . . ?
C23 C22 Cl1 119.2(4) . . ?
C24 C23 C22 117.8(4) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
C23 C24 C19 120.3(4) . . ?
C23 C24 C25 130.8(4) . . ?
C19 C24 C25 108.8(3) . . ?
C24 C25 C28 113.7(3) . . ?
C24 C25 C26 101.6(3) . . ?
C28 C25 C26 108.7(3) . . ?
C24 C25 C7 114.4(3) . . ?
C28 C25 C7 111.1(3) . . ?
C26 C25 C7 106.7(3) . . ?
O3 C26 N2 125.4(4) . . ?
O3 C26 C25 126.3(3) . . ?
N2 C26 C25 108.2(3) . . ?
N3 C27 C28 109.8(4) . . ?
N3 C27 H27 125.1 . . ?
C28 C27 H27 125.1 . . ?
C27 C28 C29 106.9(3) . . ?
C27 C28 C25 125.0(3) . . ?
C29 C28 C25 128.1(3) . . ?
C30 C29 C34 118.4(3) . . ?
C30 C29 C28 135.8(4) . . ?
C34 C29 C28 105.8(3) . . ?
C31 C30 C29 118.7(4) . . ?
C31 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
C30 C31 C32 121.8(4) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C33 C32 C31 120.9(4) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C33 C34 117.9(4) . . ?
C32 C33 H33 121.1 . . ?
C34 C33 H33 121.1 . . ?
N3 C34 C33 129.2(4) . . ?
N3 C34 C29 108.6(3) . . ?
C33 C34 C29 122.2(4) . . ?
C8 N1 C6 129.4(4) . . ?
C8 N1 H1 115.3 . . ?
C6 N1 H1 115.3 . . ?
C26 N2 C19 110.9(3) . . ?
C26 N2 C18 124.1(3) . . ?
C19 N2 C18 125.0(3) . . ?
C27 N3 C34 109.0(3) . . ?
C27 N3 H3A 125.5 . . ?
C34 N3 H3A 125.5 . . ?
C10 O2 C11 115.5(4) . . ?
C1 S1 C7 100.5(2) . . ?
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 1.395(6) . ?
C1 C6 1.397(7) . ?
C1 S1 1.754(5) . ?
C2 C3 1.378(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(6) . ?
C5 H5 0.9300 . ?
C6 N1 1.397(5) . ?
C7 C8 1.514(5) . ?
C7 C25 1.576(5) . ?
C7 S1 1.817(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.352(5) . ?
C8 N1 1.359(5) . ?
C9 C10 1.450(6) . ?
C9 H9 0.9300 . ?
C10 O1 1.220(5) . ?
C10 O2 1.334(5) . ?
C11 O2 1.447(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.393(7) . ?
C12 C17 1.393(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.333(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.517(6) . ?
C18 N2 1.461(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.378(5) . ?
C19 C20 1.392(6) . ?
C19 N2 1.405(5) . ?
C20 C21 1.380(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(6) . ?
C22 Cl1 1.746(5) . ?
C23 C24 1.374(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.507(5) . ?
C25 C28 1.516(5) . ?
C25 C26 1.552(5) . ?
C26 O3 1.222(4) . ?
C26 N2 1.354(5) . ?
C27 N3 1.370(5) . ?
C27 C28 1.371(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.457(5) . ?
C29 C30 1.389(5) . ?
C29 C34 1.404(5) . ?
C30 C31 1.370(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.403(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.339(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.403(5) . ?
C33 H33 0.9300 . ?
C34 N3 1.379(5) . ?
N1 H1 0.8600 . ?
N3 H3A 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 1.99 2.680(5) 136.2 .
N3 H3A O3 0.86 2.20 2.985(4) 151.9 2_645
