#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:22:37 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266146 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/05/7060524.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_7060524
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         'C30 H24 Cl N3 O4 S'
_chemical_formula_sum            'C30 H24 Cl N3 O4 S'
_chemical_formula_weight         558.03
_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                113.688(3)
_cell_angle_beta                 98.967(3)
_cell_angle_gamma                96.146(4)
_cell_formula_units_Z            4
_cell_length_a                   9.7808(11)
_cell_length_b                   17.785(2)
_cell_length_c                   20.680(2)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.53
_cell_measurement_theta_min      2.20
_cell_volume                     3196.2(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            43059
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.273
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0082(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     708
_refine_ls_number_reflns         11222
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0700
_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)+(0.1263P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2008
_refine_ls_wR_factor_ref         0.2209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6525
_reflns_number_total             11222
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj00947h2.cif
_cod_data_source_block           5f
_cod_depositor_comments
'Adding full bibliography for 7060515--7060528.cif.'
_cod_original_cell_volume        3196.3(6)
_cod_database_code               7060524
_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   0.937
_shelx_estimated_absorpt_t_max   0.961
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 0.6548(4) 0.4258(2) 0.1111(2) 0.0563(9) Uani 1 1 d . . . . .
C2 C 0.6243(4) 0.4483(3) 0.0552(2) 0.0697(11) Uani 1 1 d . . . . .
H2 H 0.5698 0.4891 0.0594 0.084 Uiso 1 1 calc R U . . .
C3 C 0.6725(5) 0.4119(3) -0.0069(2) 0.0870(14) Uani 1 1 d . . . . .
H3 H 0.6532 0.4291 -0.0438 0.104 Uiso 1 1 calc R U . . .
C4 C 0.7501(5) 0.3494(3) -0.0147(3) 0.0908(14) Uani 1 1 d . . . . .
H4 H 0.7814 0.3238 -0.0571 0.109 Uiso 1 1 calc R U . . .
C5 C 0.7813(4) 0.3249(3) 0.0412(2) 0.0812(13) Uani 1 1 d . . . . .
H5 H 0.8319 0.2821 0.0357 0.097 Uiso 1 1 calc R U . . .
C6 C 0.7368(4) 0.3642(3) 0.1047(2) 0.0643(10) Uani 1 1 d . . . . .
C7 C 0.6399(3) 0.3594(2) 0.21755(17) 0.0493(9) Uani 1 1 d . . . . .
C8 C 0.5646(3) 0.4200(2) 0.21339(17) 0.0471(8) Uani 1 1 d . . . . .
C9 C 0.4457(3) 0.43315(19) 0.24487(16) 0.0417(8) Uani 1 1 d . . . . .
C10 C 0.3602(4) 0.4904(2) 0.23211(19) 0.0541(9) Uani 1 1 d . . . . .
C11 C 0.1256(5) 0.5174(3) 0.2115(4) 0.1062(17) Uani 1 1 d . . . . .
H11A H 0.1680 0.5760 0.2394 0.127 Uiso 1 1 calc R U . . .
H11B H 0.0401 0.5067 0.2272 0.127 Uiso 1 1 calc R U . . .
C12 C 0.0912(9) 0.4982(6) 0.1337(5) 0.213(4) Uani 1 1 d . . . . .
H12A H 0.1757 0.5101 0.1186 0.320 Uiso 1 1 calc R U . . .
H12B H 0.0260 0.5319 0.1256 0.320 Uiso 1 1 calc R U . . .
H12C H 0.0493 0.4402 0.1063 0.320 Uiso 1 1 calc R U . . .
C13 C 0.5829(3) 0.2254(2) 0.30606(17) 0.0495(9) Uani 1 1 d . . . . .
C14 C 0.6055(4) 0.1634(3) 0.3293(2) 0.0671(10) Uani 1 1 d . . . . .
H14 H 0.6759 0.1325 0.3170 0.081 Uiso 1 1 calc R U . . .
C15 C 0.5173(4) 0.1503(3) 0.3715(2) 0.0761(12) Uani 1 1 d . . . . .
H15 H 0.5294 0.1097 0.3884 0.091 Uiso 1 1 calc R U . . .
C16 C 0.4129(4) 0.1953(3) 0.3891(2) 0.0769(12) Uani 1 1 d . . . . .
H16 H 0.3559 0.1845 0.4176 0.092 Uiso 1 1 calc R U . . .
C17 C 0.3904(4) 0.2560(3) 0.36580(19) 0.0597(10) Uani 1 1 d . . . . .
H17 H 0.3192 0.2862 0.3784 0.072 Uiso 1 1 calc R U . . .
C18 C 0.4761(3) 0.2719(2) 0.32287(16) 0.0439(8) Uani 1 1 d . . . . .
C19 C 0.4837(3) 0.3285(2) 0.28860(15) 0.0405(8) Uani 1 1 d . . . . .
C20 C 0.5972(3) 0.3125(2) 0.25266(17) 0.0449(8) Uani 1 1 d . . . . .
C21 C 0.4080(3) 0.38829(18) 0.28469(15) 0.0383(7) Uani 1 1 d . . . . .
C22 C 0.2960(3) 0.40756(19) 0.32729(15) 0.0418(8) Uani 1 1 d . . . . .
C23 C 0.3315(4) 0.4746(2) 0.39441(17) 0.0560(9) Uani 1 1 d . . . . .
H23 H 0.4204 0.5082 0.4097 0.067 Uiso 1 1 calc R U . . .
C24 C 0.2374(4) 0.4924(2) 0.43921(18) 0.0654(11) Uani 1 1 d . . . . .
C25 C 0.1062(4) 0.4432(2) 0.41679(19) 0.0674(11) Uani 1 1 d . . . . .
H25 H 0.0431 0.4546 0.4472 0.081 Uiso 1 1 calc R U . . .
C26 C 0.0676(4) 0.3771(2) 0.34943(19) 0.0585(10) Uani 1 1 d . . . . .
H26 H -0.0225 0.3448 0.3341 0.070 Uiso 1 1 calc R U . . .
C27 C 0.1615(3) 0.35823(19) 0.30428(16) 0.0427(8) Uani 1 1 d . . . . .
C28 C 0.0173(3) 0.22761(19) 0.20740(18) 0.0434(8) Uani 1 1 d . . . . .
C29 C -0.1017(6) 0.1074(3) 0.1040(3) 0.1046(17) Uani 1 1 d . . . . .
H29A H -0.0661 0.0615 0.1105 0.126 Uiso 1 1 calc R U . . .
H29B H -0.1791 0.1185 0.1285 0.126 Uiso 1 1 calc R U . . .
C30 C -0.1523(7) 0.0831(4) 0.0312(3) 0.167(3) Uani 1 1 d . . . . .
H30A H -0.2067 0.1224 0.0247 0.251 Uiso 1 1 calc R U . . .
H30B H -0.2108 0.0286 0.0105 0.251 Uiso 1 1 calc R U . . .
H30C H -0.0747 0.0815 0.0077 0.251 Uiso 1 1 calc R U . . .
C31 C 0.6657(4) 0.2479(2) 0.6869(2) 0.0755(11) Uani 1 1 d D U . . .
C32 C 0.6184(5) 0.2827(3) 0.6405(2) 0.0958(14) Uani 1 1 d D U . . .
H32 H 0.5568 0.3200 0.6524 0.115 Uiso 1 1 calc R U . . .
C33 C 0.6636(7) 0.2616(4) 0.5760(3) 0.1268(18) Uani 1 1 d D U . . .
H33 H 0.6358 0.2872 0.5460 0.152 Uiso 1 1 calc R U . . .
C34 C 0.7490(7) 0.2034(4) 0.5560(3) 0.142(2) Uani 1 1 d D U . . .
H34 H 0.7769 0.1886 0.5122 0.170 Uiso 1 1 calc R U . . .
C35 C 0.7929(6) 0.1670(4) 0.6013(3) 0.1242(18) Uani 1 1 d D U . . .
H35 H 0.8493 0.1269 0.5875 0.149 Uiso 1 1 calc R U . . .
C36 C 0.7535(5) 0.1899(3) 0.6676(2) 0.0858(13) Uani 1 1 d D U . . .
C37 C 0.6729(4) 0.1506(2) 0.76896(19) 0.0565(9) Uani 1 1 d . . . . .
C38 C 0.5935(4) 0.2118(2) 0.77967(18) 0.0520(9) Uani 1 1 d . . . . .
C39 C 0.4797(3) 0.21268(19) 0.81589(17) 0.0464(8) Uani 1 1 d . . . . .
C40 C 0.3925(4) 0.2779(2) 0.82326(19) 0.0562(9) Uani 1 1 d . . . . .
C41 C 0.1633(5) 0.3124(3) 0.8278(4) 0.115(2) Uani 1 1 d . . . . .
H41A H 0.2093 0.3619 0.8253 0.138 Uiso 1 1 calc R U . . .
H41B H 0.0777 0.2890 0.7902 0.138 Uiso 1 1 calc R U . . .
C42 C 0.1274(9) 0.3356(5) 0.8976(5) 0.184(4) Uani 1 1 d . . . . .
H42A H 0.0901 0.2861 0.9020 0.275 Uiso 1 1 calc R U . . .
H42B H 0.0579 0.3706 0.9020 0.275 Uiso 1 1 calc R U . . .
H42C H 0.2102 0.3655 0.9351 0.275 Uiso 1 1 calc R U . . .
C43 C 0.6505(4) -0.0152(2) 0.82684(19) 0.0548(9) Uani 1 1 d . . . . .
C44 C 0.6879(4) -0.0830(2) 0.8365(2) 0.0665(11) Uani 1 1 d . . . . .
H44 H 0.7592 -0.1084 0.8168 0.080 Uiso 1 1 calc R U . . .
C45 C 0.6154(5) -0.1118(2) 0.8765(2) 0.0720(11) Uani 1 1 d . . . . .
H45 H 0.6386 -0.1574 0.8842 0.086 Uiso 1 1 calc R U . . .
C46 C 0.5077(4) -0.0740(2) 0.9058(2) 0.0676(11) Uani 1 1 d . . . . .
H46 H 0.4610 -0.0943 0.9330 0.081 Uiso 1 1 calc R U . . .
C47 C 0.4700(4) -0.0072(2) 0.89467(18) 0.0531(9) Uani 1 1 d . . . . .
H47 H 0.3970 0.0171 0.9135 0.064 Uiso 1 1 calc R U . . .
C48 C 0.5421(3) 0.0241(2) 0.85484(17) 0.0449(8) Uani 1 1 d . . . . .
C49 C 0.5344(3) 0.09217(19) 0.83298(16) 0.0418(8) Uani 1 1 d . . . . .
C50 C 0.6415(3) 0.0906(2) 0.79411(18) 0.0493(8) Uani 1 1 d . . . . .
C51 C 0.4528(3) 0.15365(19) 0.84376(16) 0.0411(8) Uani 1 1 d . . . . .
C52 C 0.3424(3) 0.15766(19) 0.88701(17) 0.0422(8) Uani 1 1 d . . . . .
C53 C 0.3685(3) 0.2192(2) 0.95683(18) 0.0492(8) Uani 1 1 d . . . . .
H53 H 0.4543 0.2563 0.9766 0.059 Uiso 1 1 calc R U . . .
C54 C 0.2674(4) 0.2256(2) 0.99724(18) 0.0580(9) Uani 1 1 d . . . . .
C55 C 0.1412(4) 0.1705(2) 0.9694(2) 0.0646(11) Uani 1 1 d . . . . .
H55 H 0.0736 0.1753 0.9972 0.078 Uiso 1 1 calc R U . . .
C56 C 0.1148(4) 0.1080(2) 0.8999(2) 0.0628(10) Uani 1 1 d . . . . .
H56 H 0.0295 0.0704 0.8809 0.075 Uiso 1 1 calc R U . . .
C57 C 0.2152(3) 0.1011(2) 0.85843(18) 0.0482(8) Uani 1 1 d . . . . .
C58 C 0.0752(4) -0.0168(2) 0.7463(2) 0.0584(9) Uani 1 1 d . . . . .
C59 C -0.0254(5) -0.1270(3) 0.6337(3) 0.132(2) Uani 1 1 d D . . . .
H59A H -0.0860 -0.0999 0.6119 0.159 Uiso 1 1 calc R U . . .
H59B H -0.0782 -0.1482 0.6609 0.159 Uiso 1 1 calc R U . . .
C60 C 0.0122(8) -0.1985(4) 0.5754(4) 0.214(4) Uani 1 1 d D . . . .
H60A H 0.0397 -0.1810 0.5403 0.321 Uiso 1 1 calc R U . . .
H60B H -0.0678 -0.2434 0.5525 0.321 Uiso 1 1 calc R U . . .
H60C H 0.0890 -0.2172 0.5959 0.321 Uiso 1 1 calc R U . . .
Cl1 Cl 0.28535(15) 0.57761(9) 0.52297(6) 0.1137(5) Uani 1 1 d . . . . .
Cl2 Cl 0.29777(13) 0.30477(7) 1.08404(6) 0.0904(4) Uani 1 1 d . . . . .
N1 N 0.6060(3) 0.46467(18) 0.17504(16) 0.0585(8) Uani 1 1 d . . . . .
H1 H 0.6016 0.5169 0.1908 0.070 Uiso 1 1 calc R U . . .
N2 N 0.6558(3) 0.25135(17) 0.26395(15) 0.0522(7) Uani 1 1 d . . . . .
H2A H 0.7265 0.2320 0.2476 0.063 Uiso 1 1 calc R U . . .
N3 N 0.1263(3) 0.29252(16) 0.23420(13) 0.0476(7) Uani 1 1 d . . . . .
H3A H 0.1801 0.2940 0.2054 0.057 Uiso 1 1 calc R U . . .
N4 N 0.6224(3) 0.27012(19) 0.75231(16) 0.0692(9) Uani 1 1 d . . . . .
H4A H 0.6135 0.3209 0.7762 0.083 Uiso 1 1 calc R U . . .
N5 N 0.7094(3) 0.02553(19) 0.79035(16) 0.0614(8) Uani 1 1 d . . . . .
H5A H 0.7775 0.0123 0.7688 0.074 Uiso 1 1 calc R U . . .
N6 N 0.1943(3) 0.03933(18) 0.78731(15) 0.0630(9) Uani 1 1 d . . . . .
H6 H 0.2656 0.0368 0.7674 0.076 Uiso 1 1 calc R U . . .
O1 O 0.4043(3) 0.55228(18) 0.2260(2) 0.0973(11) Uani 1 1 d . . . . .
O2 O 0.2235(2) 0.46551(14) 0.22410(14) 0.0613(7) Uani 1 1 d . . . . .
O3 O -0.0631(2) 0.21173(14) 0.24100(13) 0.0598(6) Uani 1 1 d . . . . .
O4 O 0.0100(2) 0.18131(14) 0.13784(12) 0.0630(7) Uani 1 1 d . . . . .
O5 O 0.4395(3) 0.34895(17) 0.83385(16) 0.0761(8) Uani 1 1 d . . . . .
O6 O 0.2570(3) 0.25096(17) 0.81476(18) 0.0855(9) Uani 1 1 d . . . . .
O7 O -0.0346(2) -0.02404(17) 0.76449(15) 0.0819(9) Uani 1 1 d . . . . .
O8 O 0.0970(3) -0.06560(18) 0.68327(14) 0.0911(10) Uani 1 1 d D . . . .
S1 S 0.79063(10) 0.34352(8) 0.17965(6) 0.0774(4) Uani 1 1 d . . . . .
S2 S 0.81809(12) 0.14930(8) 0.72801(7) 0.0914(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 119.4(3) . . ?
C2 C1 N1 120.7(4) . . ?
C6 C1 N1 119.9(3) . . ?
C1 C2 C3 121.3(4) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.9(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 S1 121.1(3) . . ?
C1 C6 S1 119.2(3) . . ?
C20 C7 C8 119.2(3) . . ?
C20 C7 S1 120.2(3) . . ?
C8 C7 S1 120.7(2) . . ?
C7 C8 N1 118.4(3) . . ?
C7 C8 C9 120.2(3) . . ?
N1 C8 C9 121.3(3) . . ?
C8 C9 C21 120.1(3) . . ?
C8 C9 C10 118.4(3) . . ?
C21 C9 C10 121.5(3) . . ?
O1 C10 O2 121.4(3) . . ?
O1 C10 C9 125.3(3) . . ?
O2 C10 C9 113.2(3) . . ?
O2 C11 C12 109.8(5) . . ?
O2 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
O2 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 128.2(3) . . ?
N2 C13 C18 109.0(3) . . ?
C14 C13 C18 122.8(3) . . ?
C15 C14 C13 116.4(4) . . ?
C15 C14 H14 121.8 . . ?
C13 C14 H14 121.8 . . ?
C16 C15 C14 121.9(4) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 121.6(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C18 119.1(4) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 118.3(3) . . ?
C17 C18 C19 134.8(3) . . ?
C13 C18 C19 106.9(3) . . ?
C21 C19 C20 119.9(3) . . ?
C21 C19 C18 134.5(3) . . ?
C20 C19 C18 105.7(3) . . ?
N2 C20 C7 129.0(3) . . ?
N2 C20 C19 109.5(3) . . ?
C7 C20 C19 121.3(3) . . ?
C19 C21 C9 119.1(3) . . ?
C19 C21 C22 118.3(3) . . ?
C9 C21 C22 122.4(3) . . ?
C23 C22 C27 119.1(3) . . ?
C23 C22 C21 117.6(3) . . ?
C27 C22 C21 123.2(3) . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C23 119.7(3) . . ?
C25 C24 Cl1 120.6(3) . . ?
C23 C24 Cl1 119.7(3) . . ?
C24 C25 C26 120.2(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C27 120.5(3) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C22 119.4(3) . . ?
C26 C27 N3 122.8(3) . . ?
C22 C27 N3 117.7(2) . . ?
O3 C28 O4 123.5(3) . . ?
O3 C28 N3 126.0(3) . . ?
O4 C28 N3 110.5(3) . . ?
C30 C29 O4 113.9(4) . . ?
C30 C29 H29A 108.8 . . ?
O4 C29 H29A 108.8 . . ?
C30 C29 H29B 108.8 . . ?
O4 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C36 120.0(4) . . ?
C32 C31 N4 119.8(4) . . ?
C36 C31 N4 120.2(3) . . ?
C31 C32 C33 119.6(5) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C34 C33 C32 120.7(5) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 119.6(6) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C36 120.6(5) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C31 C36 C35 119.4(4) . . ?
C31 C36 S2 119.7(3) . . ?
C35 C36 S2 120.9(4) . . ?
C38 C37 C50 118.9(3) . . ?
C38 C37 S2 121.6(3) . . ?
C50 C37 S2 119.5(3) . . ?
C37 C38 N4 118.6(3) . . ?
C37 C38 C39 119.9(3) . . ?
N4 C38 C39 121.4(3) . . ?
C51 C39 C38 120.6(3) . . ?
C51 C39 C40 121.5(3) . . ?
C38 C39 C40 117.9(3) . . ?
O5 C40 O6 122.5(3) . . ?
O5 C40 C39 123.8(3) . . ?
O6 C40 C39 113.7(3) . . ?
C42 C41 O6 111.7(5) . . ?
C42 C41 H41A 109.3 . . ?
O6 C41 H41A 109.3 . . ?
C42 C41 H41B 109.3 . . ?
O6 C41 H41B 109.3 . . ?
H41A C41 H41B 107.9 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 N5 127.8(3) . . ?
C44 C43 C48 123.1(4) . . ?
N5 C43 C48 109.1(3) . . ?
C43 C44 C45 117.3(4) . . ?
C43 C44 H44 121.4 . . ?
C45 C44 H44 121.4 . . ?
C44 C45 C46 121.3(4) . . ?
C44 C45 H45 119.4 . . ?
C46 C45 H45 119.4 . . ?
C47 C46 C45 120.7(4) . . ?
C47 C46 H46 119.6 . . ?
C45 C46 H46 119.6 . . ?
C46 C47 C48 119.5(3) . . ?
C46 C47 H47 120.3 . . ?
C48 C47 H47 120.3 . . ?
C47 C48 C43 118.1(3) . . ?
C47 C48 C49 135.3(3) . . ?
C43 C48 C49 106.6(3) . . ?
C51 C49 C50 119.0(3) . . ?
C51 C49 C48 135.0(3) . . ?
C50 C49 C48 105.9(3) . . ?
N5 C50 C37 128.1(3) . . ?
N5 C50 C49 109.3(3) . . ?
C37 C50 C49 122.5(3) . . ?
C49 C51 C39 119.0(3) . . ?
C49 C51 C52 119.4(3) . . ?
C39 C51 C52 121.5(3) . . ?
C53 C52 C57 119.7(3) . . ?
C53 C52 C51 118.7(3) . . ?
C57 C52 C51 121.5(3) . . ?
C54 C53 C52 120.0(3) . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C55 C54 C53 120.8(3) . . ?
C55 C54 Cl2 119.1(3) . . ?
C53 C54 Cl2 120.1(3) . . ?
C54 C55 C56 119.7(3) . . ?
C54 C55 H55 120.2 . . ?
C56 C55 H55 120.2 . . ?
C55 C56 C57 120.2(3) . . ?
C55 C56 H56 119.9 . . ?
C57 C56 H56 119.9 . . ?
C56 C57 C52 119.7(3) . . ?
C56 C57 N6 122.8(3) . . ?
C52 C57 N6 117.5(3) . . ?
O7 C58 O8 123.6(3) . . ?
O7 C58 N6 126.3(3) . . ?
O8 C58 N6 110.1(3) . . ?
O8 C59 C60 113.0(4) . . ?
O8 C59 H59A 109.0 . . ?
C60 C59 H59A 109.0 . . ?
O8 C59 H59B 109.0 . . ?
C60 C59 H59B 109.0 . . ?
H59A C59 H59B 107.8 . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C8 N1 C1 121.3(3) . . ?
C8 N1 H1 119.3 . . ?
C1 N1 H1 119.3 . . ?
C20 N2 C13 108.9(3) . . ?
C20 N2 H2A 125.6 . . ?
C13 N2 H2A 125.6 . . ?
C28 N3 C27 127.0(3) . . ?
C28 N3 H3A 116.5 . . ?
C27 N3 H3A 116.5 . . ?
C38 N4 C31 121.4(3) . . ?
C38 N4 H4A 119.3 . . ?
C31 N4 H4A 119.3 . . ?
C50 N5 C43 109.0(3) . . ?
C50 N5 H5A 125.5 . . ?
C43 N5 H5A 125.5 . . ?
C58 N6 C57 127.8(3) . . ?
C58 N6 H6 116.1 . . ?
C57 N6 H6 116.1 . . ?
C10 O2 C11 119.0(3) . . ?
C28 O4 C29 115.0(3) . . ?
C40 O6 C41 118.0(3) . . ?
C58 O8 C59 115.0(3) . . ?
C6 S1 C7 99.12(17) . . ?
C36 S2 C37 98.56(19) . . ?
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 1.369(5) . ?
C1 C6 1.403(5) . ?
C1 N1 1.410(4) . ?
C2 C3 1.370(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9300 . ?
C6 S1 1.748(4) . ?
C7 C20 1.380(4) . ?
C7 C8 1.390(5) . ?
C7 S1 1.772(3) . ?
C8 N1 1.401(4) . ?
C8 C9 1.415(4) . ?
C9 C21 1.418(4) . ?
C9 C10 1.461(5) . ?
C10 O1 1.201(4) . ?
C10 O2 1.325(4) . ?
C11 O2 1.463(5) . ?
C11 C12 1.478(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N2 1.388(4) . ?
C13 C14 1.393(5) . ?
C13 C18 1.401(5) . ?
C14 C15 1.385(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.397(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.448(4) . ?
C19 C21 1.379(4) . ?
C19 C20 1.421(4) . ?
C20 N2 1.365(4) . ?
C21 C22 1.494(4) . ?
C22 C23 1.378(4) . ?
C22 C27 1.396(4) . ?
C23 C24 1.378(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.369(5) . ?
C24 Cl1 1.732(3) . ?
C25 C26 1.375(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.382(4) . ?
C26 H26 0.9300 . ?
C27 N3 1.408(4) . ?
C28 O3 1.209(4) . ?
C28 O4 1.325(4) . ?
C28 N3 1.347(4) . ?
C29 C30 1.377(7) . ?
C29 O4 1.459(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.384(4) . ?
C31 C36 1.387(4) . ?
C31 N4 1.398(5) . ?
C32 C33 1.390(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.374(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.379(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.395(4) . ?
C35 H35 0.9300 . ?
C36 S2 1.748(5) . ?
C37 C38 1.370(5) . ?
C37 C50 1.389(5) . ?
C37 S2 1.761(3) . ?
C38 N4 1.391(4) . ?
C38 C39 1.433(4) . ?
C39 C51 1.406(4) . ?
C39 C40 1.486(5) . ?
C40 O5 1.215(4) . ?
C40 O6 1.319(4) . ?
C41 C42 1.445(8) . ?
C41 O6 1.470(5) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 C44 1.376(5) . ?
C43 N5 1.382(4) . ?
C43 C48 1.404(4) . ?
C44 C45 1.378(6) . ?
C44 H44 0.9300 . ?
C45 C46 1.397(6) . ?
C45 H45 0.9300 . ?
C46 C47 1.374(5) . ?
C46 H46 0.9300 . ?
C47 C48 1.397(4) . ?
C47 H47 0.9300 . ?
C48 C49 1.457(4) . ?
C49 C51 1.389(4) . ?
C49 C50 1.413(4) . ?
C50 N5 1.376(4) . ?
C51 C52 1.495(4) . ?
C52 C53 1.379(4) . ?
C52 C57 1.391(4) . ?
C53 C54 1.376(4) . ?
C53 H53 0.9300 . ?
C54 C55 1.372(5) . ?
C54 Cl2 1.734(3) . ?
C55 C56 1.381(5) . ?
C55 H55 0.9300 . ?
C56 C57 1.385(4) . ?
C56 H56 0.9300 . ?
C57 N6 1.404(4) . ?
C58 O7 1.202(4) . ?
C58 O8 1.310(4) . ?
C58 N6 1.355(4) . ?
C59 O8 1.454(4) . ?
C59 C60 1.487(4) . ?
C59 H59A 0.9700 . ?
C59 H59B 0.9700 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?
N3 H3A 0.8600 . ?
N4 H4A 0.8600 . ?
N5 H5A 0.8600 . ?
N6 H6 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 2.23 2.723(4) 116.3 .
N2 H2A O3 0.86 2.14 2.972(4) 161.7 1_655
N4 H4A O1 0.86 2.30 3.053(4) 146.6 2_666
N4 H4A O5 0.86 2.21 2.755(4) 120.7 .
N5 H5A O7 0.86 2.02 2.801(4) 151.3 1_655
