#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024502.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_4024502
loop_
_publ_author_name
'Jing Sun'
'Li-Li Zhang'
'Er-Yan Xia'
'Chao-Guo Yan'
_publ_contact_author_address
;
      College of Chemistry & Chemical Engineering
      Yangzhou University
      Yangzhou 225002, 
      P.R. China
;
_publ_contact_author_email       cgyan@yzu.edu.cn
_publ_contact_author_fax         +86-514-7975590-8401
_publ_contact_author_name        'Chao Guo Yan'
_publ_contact_author_phone       +86-514-7975531
_publ_section_title
;
Synthesis of Dihydrothiophenes or Spirocyclic Compounds by Domino Reactions
of 1,3-Thiazolidinedione
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3398
_journal_page_last               3401
_journal_paper_doi               10.1021/jo900215a
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C23 H13 Cl2 N5 O2 S, C4 H11 N, C3 H7 N O'
_chemical_formula_sum            'C30 H31 Cl2 N7 O3 S'
_chemical_formula_weight         640.58
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.936(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.222(16)
_cell_length_b                   13.940(10)
_cell_length_c                   21.503(15)
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.599
_cell_measurement_theta_min      2.304
_cell_volume                     6457(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            44410
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colours
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2672
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.076
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     783
_refine_ls_number_reflns         11477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1026P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1717
_reflns_number_gt                8322
_reflns_number_total             11477
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900215a_si_001_10.cif
_cod_data_source_block           7i
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024502
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.54831(11) -0.05239(19) 0.25629(12) 0.0240(6) Uani 1 1 d . . .
H1 H 0.5626 -0.1183 0.2555 0.029 Uiso 1 1 calc R . .
C2 C 0.54513(12) -0.03921(19) 0.32485(13) 0.0258(6) Uani 1 1 d . . .
C3 C 0.49798(12) -0.00178(19) 0.33968(13) 0.0266(6) Uani 1 1 d . . .
C4 C 0.43885(11) 0.03481(19) 0.28297(13) 0.0245(6) Uani 1 1 d . . .
C5 C 0.44589(11) 0.03980(18) 0.21284(12) 0.0226(6) Uani 1 1 d . . .
H5 H 0.4732 0.0947 0.2162 0.027 Uiso 1 1 calc R . .
C6 C 0.48156(12) -0.04816(18) 0.20123(13) 0.0231(6) Uani 1 1 d . . .
C7 C 0.48440(11) -0.03988(19) 0.13082(13) 0.0249(6) Uani 1 1 d . . .
C8 C 0.44941(12) -0.1937(2) 0.11930(14) 0.0309(6) Uani 1 1 d . . .
C9 C 0.59822(11) 0.01206(19) 0.24729(12) 0.0236(6) Uani 1 1 d . . .
C10 C 0.60486(12) 0.1088(2) 0.26606(14) 0.0303(6) Uani 1 1 d . . .
H10 H 0.5775 0.1363 0.2833 0.036 Uiso 1 1 calc R . .
C11 C 0.65199(12) 0.1647(2) 0.25925(15) 0.0343(7) Uani 1 1 d . . .
H11 H 0.6549 0.2297 0.2697 0.041 Uiso 1 1 calc R . .
C12 C 0.69412(12) 0.1221(2) 0.23682(15) 0.0342(7) Uani 1 1 d . . .
C13 C 0.68908(13) 0.0262(2) 0.21887(16) 0.0386(7) Uani 1 1 d . . .
H13 H 0.7177 -0.0018 0.2036 0.046 Uiso 1 1 calc R . .
C14 C 0.64080(12) -0.0276(2) 0.22395(14) 0.0309(6) Uani 1 1 d . . .
H14 H 0.6370 -0.0919 0.2114 0.037 Uiso 1 1 calc R . .
C15 C 0.38417(12) 0.06663(19) 0.15737(13) 0.0255(6) Uani 1 1 d . . .
C16 C 0.37542(13) 0.1599(2) 0.13284(14) 0.0315(6) Uani 1 1 d . . .
H16 H 0.4080 0.2034 0.1491 0.038 Uiso 1 1 calc R . .
C17 C 0.31947(13) 0.1901(2) 0.08473(15) 0.0375(7) Uani 1 1 d . . .
H17 H 0.3145 0.2531 0.0693 0.045 Uiso 1 1 calc R . .
C18 C 0.27164(13) 0.1252(2) 0.06041(14) 0.0374(7) Uani 1 1 d . . .
C19 C 0.27851(13) 0.0313(2) 0.08301(14) 0.0357(7) Uani 1 1 d . . .
H19 H 0.2457 -0.0117 0.0661 0.043 Uiso 1 1 calc R . .
C20 C 0.33448(12) 0.0017(2) 0.13100(14) 0.0316(6) Uani 1 1 d . . .
H20 H 0.3392 -0.0615 0.1459 0.038 Uiso 1 1 calc R . .
C21 C 0.59954(13) -0.0686(2) 0.38068(14) 0.0326(7) Uani 1 1 d . . .
C22 C 0.38670(13) -0.0292(2) 0.28162(14) 0.0301(6) Uani 1 1 d . . .
C23 C 0.42396(12) 0.1335(2) 0.29897(13) 0.0279(6) Uani 1 1 d . . .
C24 C 0.58649(18) 0.2233(3) 0.0825(2) 0.0744(13) Uani 1 1 d . . .
H24A H 0.5886 0.1693 0.1110 0.112 Uiso 1 1 calc R . .
H24B H 0.6081 0.2766 0.1094 0.112 Uiso 1 1 calc R . .
H24C H 0.6055 0.2069 0.0512 0.112 Uiso 1 1 calc R . .
C25 C 0.52036(18) 0.2498(2) 0.04529(18) 0.0546(10) Uani 1 1 d . . .
H25A H 0.5179 0.3002 0.0133 0.065 Uiso 1 1 calc R . .
H25B H 0.5025 0.2739 0.0764 0.065 Uiso 1 1 calc R . .
C26 C 0.41678(15) 0.1836(3) -0.02746(17) 0.0535(9) Uani 1 1 d . . .
H26A H 0.4111 0.2220 -0.0669 0.064 Uiso 1 1 calc R . .
H26B H 0.4010 0.2198 0.0013 0.064 Uiso 1 1 calc R . .
C27 C 0.38119(17) 0.0916(3) -0.04803(19) 0.0718(13) Uani 1 1 d . . .
H27A H 0.3971 0.0556 -0.0762 0.108 Uiso 1 1 calc R . .
H27B H 0.3381 0.1056 -0.0722 0.108 Uiso 1 1 calc R . .
H27C H 0.3856 0.0546 -0.0088 0.108 Uiso 1 1 calc R . .
C28 C 1.05346(11) -0.02221(18) 0.26220(12) 0.0208(5) Uani 1 1 d . . .
H28 H 1.0685 -0.0881 0.2629 0.025 Uiso 1 1 calc R . .
C29 C 1.05131(11) -0.00429(19) 0.33111(12) 0.0229(6) Uani 1 1 d . . .
C30 C 1.00420(11) 0.03230(18) 0.34628(12) 0.0207(5) Uani 1 1 d . . .
C31 C 0.94384(11) 0.06553(18) 0.28931(11) 0.0192(5) Uani 1 1 d . . .
C32 C 0.95127(11) 0.06909(18) 0.21952(11) 0.0203(5) Uani 1 1 d . . .
H32 H 0.9793 0.1231 0.2227 0.024 Uiso 1 1 calc R . .
C33 C 0.89041(11) 0.09516(19) 0.16250(12) 0.0228(6) Uani 1 1 d . . .
C34 C 0.88367(13) 0.1883(2) 0.13665(13) 0.0300(6) Uani 1 1 d . . .
H34 H 0.9162 0.2316 0.1540 0.036 Uiso 1 1 calc R . .
C35 C 0.82937(14) 0.2174(2) 0.08554(14) 0.0381(7) Uani 1 1 d . . .
H35 H 0.8255 0.2795 0.0687 0.046 Uiso 1 1 calc R . .
C36 C 0.78144(14) 0.1529(2) 0.06021(14) 0.0366(7) Uani 1 1 d . . .
C37 C 0.78650(13) 0.0601(2) 0.08475(14) 0.0351(7) Uani 1 1 d . . .
H37 H 0.7537 0.0172 0.0671 0.042 Uiso 1 1 calc R . .
C38 C 0.84062(12) 0.0319(2) 0.13572(13) 0.0289(6) Uani 1 1 d . . .
H38 H 0.8440 -0.0303 0.1525 0.035 Uiso 1 1 calc R . .
C39 C 1.10126(11) 0.04290(19) 0.24908(12) 0.0230(6) Uani 1 1 d . . .
C40 C 1.13651(12) 0.0049(2) 0.21507(13) 0.0299(6) Uani 1 1 d . . .
H40 H 1.1305 -0.0587 0.2009 0.036 Uiso 1 1 calc R . .
C41 C 1.18004(13) 0.0594(2) 0.20205(14) 0.0381(7) Uani 1 1 d . . .
H41 H 1.2032 0.0333 0.1790 0.046 Uiso 1 1 calc R . .
C42 C 1.18899(12) 0.1542(2) 0.22373(15) 0.0353(7) Uani 1 1 d . . .
C43 C 1.15548(12) 0.1932(2) 0.25846(14) 0.0327(7) Uani 1 1 d . . .
H43 H 1.1618 0.2566 0.2729 0.039 Uiso 1 1 calc R . .
C44 C 1.11203(12) 0.13696(19) 0.27189(13) 0.0268(6) Uani 1 1 d . . .
H44 H 1.0900 0.1625 0.2963 0.032 Uiso 1 1 calc R . .
C45 C 1.10652(13) -0.0295(2) 0.38601(13) 0.0321(7) Uani 1 1 d . . .
C46 C 0.92796(11) 0.1652(2) 0.30377(12) 0.0228(6) Uani 1 1 d . . .
C47 C 0.89157(12) 0.00345(18) 0.28913(12) 0.0224(6) Uani 1 1 d . . .
C2S C 0.25398(16) 0.5620(4) 0.0912(2) 0.0858(15) Uani 1 1 d . . .
H2S1 H 0.2662 0.5533 0.0536 0.129 Uiso 1 1 calc R . .
H2S2 H 0.2836 0.5312 0.1299 0.129 Uiso 1 1 calc R . .
H2S3 H 0.2524 0.6292 0.1000 0.129 Uiso 1 1 calc R . .
C3S C 0.14470(16) 0.5736(3) 0.06428(15) 0.0541(10) Uani 1 1 d . . .
H3S H 0.1518 0.6388 0.0728 0.065 Uiso 1 1 calc R . .
O1S O 0.08973(10) 0.5468(2) 0.04251(12) 0.0681(8) Uani 1 1 d . . .
C52 C 1.04003(18) 0.2893(2) 0.09784(16) 0.0548(10) Uani 1 1 d . . .
H52A H 1.0023 0.3260 0.0816 0.082 Uiso 1 1 calc R . .
H52B H 1.0744 0.3311 0.1200 0.082 Uiso 1 1 calc R . .
H52C H 1.0373 0.2417 0.1289 0.082 Uiso 1 1 calc R . .
C53 C 1.04949(17) 0.2405(2) 0.03960(15) 0.0455(8) Uani 1 1 d . . .
H53A H 1.0457 0.2877 0.0052 0.055 Uiso 1 1 calc R . .
H53B H 1.0912 0.2143 0.0547 0.055 Uiso 1 1 calc R . .
C54 C 0.93703(15) 0.1917(2) -0.02125(15) 0.0436(8) Uani 1 1 d . . .
H54A H 0.9315 0.2331 -0.0593 0.052 Uiso 1 1 calc R . .
H54B H 0.9259 0.2277 0.0112 0.052 Uiso 1 1 calc R . .
C55 C 0.89586(15) 0.1058(3) -0.04378(17) 0.0601(11) Uani 1 1 d . . .
H55A H 0.9084 0.0686 -0.0742 0.090 Uiso 1 1 calc R . .
H55B H 0.8536 0.1262 -0.0660 0.090 Uiso 1 1 calc R . .
H55C H 0.8992 0.0673 -0.0056 0.090 Uiso 1 1 calc R . .
Cl1 Cl 0.75549(4) 0.19011(6) 0.23170(5) 0.0574(3) Uani 1 1 d . . .
Cl2 Cl 0.20050(4) 0.16330(7) 0.00130(4) 0.0568(3) Uani 1 1 d . . .
Cl3 Cl 0.71239(4) 0.19000(7) -0.00359(4) 0.0597(3) Uani 1 1 d . . .
Cl4 Cl 1.24556(4) 0.22314(7) 0.20888(5) 0.0567(3) Uani 1 1 d . . .
N1 N 0.64275(12) -0.0919(2) 0.42551(13) 0.0490(7) Uani 1 1 d . . .
N2 N 0.34728(12) -0.0773(2) 0.28306(13) 0.0449(7) Uani 1 1 d . . .
N3 N 0.47100(10) -0.11904(16) 0.09339(11) 0.0289(5) Uani 1 1 d . . .
H3 H 0.4756 -0.1227 0.0556 0.035 Uiso 1 1 calc R . .
N4 N 0.49644(11) 0.00487(18) 0.40146(11) 0.0353(6) Uani 1 1 d . . .
H4A H 0.5272 -0.0157 0.4356 0.042 Uiso 1 1 calc R . .
H4B H 0.4647 0.0297 0.4068 0.042 Uiso 1 1 calc R . .
N5 N 0.48437(11) 0.16384(17) 0.00901(11) 0.0336(6) Uani 1 1 d . . .
H5A H 0.4884 0.1169 0.0391 0.040 Uiso 1 1 d R . .
N6 N 0.41229(11) 0.20999(18) 0.31042(12) 0.0375(6) Uani 1 1 d . . .
N7 N 1.15179(13) -0.0492(2) 0.42979(12) 0.0542(8) Uani 1 1 d . . .
N8 N 1.00495(10) 0.04318(16) 0.40887(10) 0.0256(5) Uani 1 1 d . . .
H8A H 1.0371 0.0263 0.4428 0.031 Uiso 1 1 calc R . .
H8B H 0.9732 0.0670 0.4148 0.031 Uiso 1 1 calc R . .
N9 N 0.91383(10) 0.24117(17) 0.31220(11) 0.0321(6) Uani 1 1 d . . .
N10 N 0.85093(10) -0.04264(17) 0.29012(11) 0.0307(5) Uani 1 1 d . . .
N1S N 0.19311(12) 0.5198(2) 0.07635(12) 0.0444(7) Uani 1 1 d . . .
N12 N 1.00326(11) 0.16069(16) 0.00968(10) 0.0283(5) Uani 1 1 d . . .
H12A H 1.0066 0.1181 0.0423 0.034 Uiso 1 1 d R . .
O1 O 0.50012(8) 0.03850(14) 0.11424(9) 0.0302(4) Uani 1 1 d . . .
O2 O 0.43317(10) -0.27282(15) 0.09487(10) 0.0420(5) Uani 1 1 d . . .
S2 S 0.95035(3) -0.13624(5) 0.21338(3) 0.02314(17) Uani 1 1 d . . .
S1 S 0.44523(3) -0.16462(5) 0.20016(4) 0.02882(18) Uani 1 1 d . . .
O4 O 1.00262(8) 0.05796(13) 0.11812(8) 0.0263(4) Uani 1 1 d . . .
O3 O 0.93011(9) -0.24885(13) 0.10821(9) 0.0325(5) Uani 1 1 d . . .
N11 N 0.96848(9) -0.09837(15) 0.10099(10) 0.0231(5) Uani 1 1 d . . .
H11A H 0.9697 -0.1044 0.0617 0.028 Uiso 1 1 calc R . .
C58 C 0.94854(11) -0.16976(19) 0.13084(12) 0.0235(6) Uani 1 1 d . . .
C57 C 0.98609(11) -0.01789(18) 0.13705(12) 0.0209(5) Uani 1 1 d . . .
C56 C 0.98595(11) -0.02076(17) 0.20903(12) 0.0191(5) Uani 1 1 d . . .
C1S C 0.1882(3) 0.4177(3) 0.0643(3) 0.0983(17) Uani 1 1 d . . .
H1S1 H 0.1463 0.3975 0.0548 0.147 Uiso 1 1 calc R . .
H1S2 H 0.2156 0.3847 0.1033 0.147 Uiso 1 1 calc R . .
H1S3 H 0.1995 0.4031 0.0267 0.147 Uiso 1 1 calc R . .
O2S O 0.41446(11) 0.0525(2) 0.46731(12) 0.0621(8) Uani 1 1 d . . .
N2S N 0.31720(12) -0.0065(2) 0.41444(14) 0.0538(8) Uani 1 1 d . . .
C6S C 0.3745(2) -0.0175(4) 0.4535(2) 0.0730(13) Uani 1 1 d . . .
H6S H 0.3878 -0.0774 0.4724 0.088 Uiso 1 1 calc R . .
C5S C 0.2761(2) -0.0921(4) 0.3924(3) 0.0968(17) Uani 1 1 d . . .
H5S1 H 0.2691 -0.1061 0.3464 0.145 Uiso 1 1 calc R . .
H5S2 H 0.2372 -0.0793 0.3967 0.145 Uiso 1 1 calc R . .
H5S3 H 0.2957 -0.1462 0.4198 0.145 Uiso 1 1 calc R . .
C4S C 0.2898(3) 0.0803(4) 0.3848(3) 0.123(2) Uani 1 1 d . . .
H4S1 H 0.3178 0.1323 0.4045 0.184 Uiso 1 1 calc R . .
H4S2 H 0.2519 0.0899 0.3920 0.184 Uiso 1 1 calc R . .
H4S3 H 0.2812 0.0780 0.3375 0.184 Uiso 1 1 calc R . .
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 C9 111.4(2) . . ?
C2 C1 C6 109.8(2) . . ?
C9 C1 C6 117.7(2) . . ?
C2 C1 H1 105.7 . . ?
C9 C1 H1 105.7 . . ?
C6 C1 H1 105.7 . . ?
C3 C2 C21 116.6(2) . . ?
C3 C2 C1 127.9(2) . . ?
C21 C2 C1 115.5(2) . . ?
N4 C3 C2 125.5(2) . . ?
N4 C3 C4 114.4(2) . . ?
C2 C3 C4 120.0(2) . . ?
C23 C4 C22 107.4(2) . . ?
C23 C4 C3 109.7(2) . . ?
C22 C4 C3 107.0(2) . . ?
C23 C4 C5 107.2(2) . . ?
C22 C4 C5 112.3(2) . . ?
C3 C4 C5 113.0(2) . . ?
C15 C5 C6 118.0(2) . . ?
C15 C5 C4 110.8(2) . . ?
C6 C5 C4 111.8(2) . . ?
C15 C5 H5 105.0 . . ?
C6 C5 H5 105.0 . . ?
C4 C5 H5 105.0 . . ?
C7 C6 C5 108.6(2) . . ?
C7 C6 C1 110.6(2) . . ?
C5 C6 C1 110.3(2) . . ?
C7 C6 S1 104.06(17) . . ?
C5 C6 S1 115.65(18) . . ?
C1 C6 S1 107.41(17) . . ?
O1 C7 N3 125.5(2) . . ?
O1 C7 C6 118.1(2) . . ?
N3 C7 C6 116.4(2) . . ?
O2 C8 N3 128.1(3) . . ?
O2 C8 S1 119.6(2) . . ?
N3 C8 S1 112.3(2) . . ?
C14 C9 C10 118.3(2) . . ?
C14 C9 C1 119.2(2) . . ?
C10 C9 C1 122.3(2) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 Cl1 119.4(2) . . ?
C13 C12 Cl1 119.5(2) . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 121.4(3) . . ?
C9 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C20 117.8(2) . . ?
C16 C15 C5 119.1(2) . . ?
C20 C15 C5 123.0(2) . . ?
C15 C16 C17 122.0(3) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C18 C17 C16 118.7(3) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 C19 121.2(3) . . ?
C17 C18 Cl2 119.1(2) . . ?
C19 C18 Cl2 119.7(2) . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C15 120.5(3) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
N1 C21 C2 179.5(3) . . ?
N2 C22 C4 177.4(3) . . ?
N6 C23 C4 179.1(3) . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C24 C25 N5 110.1(3) . . ?
C24 C25 H25A 109.6 . . ?
N5 C25 H25A 109.6 . . ?
C24 C25 H25B 109.6 . . ?
N5 C25 H25B 109.6 . . ?
H25A C25 H25B 108.2 . . ?
N5 C26 C27 110.6(3) . . ?
N5 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
N5 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C39 111.7(2) . . ?
C29 C28 C56 108.8(2) . . ?
C39 C28 C56 117.0(2) . . ?
C29 C28 H28 106.2 . . ?
C39 C28 H28 106.2 . . ?
C56 C28 H28 106.2 . . ?
C30 C29 C45 116.8(2) . . ?
C30 C29 C28 128.3(2) . . ?
C45 C29 C28 114.8(2) . . ?
N8 C30 C29 125.0(2) . . ?
N8 C30 C31 115.2(2) . . ?
C29 C30 C31 119.8(2) . . ?
C47 C31 C46 106.0(2) . . ?
C47 C31 C30 108.9(2) . . ?
C46 C31 C30 109.46(19) . . ?
C47 C31 C32 113.29(19) . . ?
C46 C31 C32 106.9(2) . . ?
C30 C31 C32 111.99(19) . . ?
C33 C32 C56 116.7(2) . . ?
C33 C32 C31 112.0(2) . . ?
C56 C32 C31 111.17(19) . . ?
C33 C32 H32 105.3 . . ?
C56 C32 H32 105.3 . . ?
C31 C32 H32 105.3 . . ?
C34 C33 C38 118.1(2) . . ?
C34 C33 C32 118.2(2) . . ?
C38 C33 C32 123.7(2) . . ?
C35 C34 C33 121.3(3) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C36 C35 C34 118.9(3) . . ?
C36 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
C35 C36 C37 121.3(3) . . ?
C35 C36 Cl3 119.0(2) . . ?
C37 C36 Cl3 119.7(2) . . ?
C38 C37 C36 119.4(3) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C37 C38 C33 121.0(3) . . ?
C37 C38 H38 119.5 . . ?
C33 C38 H38 119.5 . . ?
C44 C39 C40 118.8(2) . . ?
C44 C39 C28 122.6(2) . . ?
C40 C39 C28 118.6(2) . . ?
C41 C40 C39 121.2(3) . . ?
C41 C40 H40 119.4 . . ?
C39 C40 H40 119.4 . . ?
C40 C41 C42 119.1(3) . . ?
C40 C41 H41 120.4 . . ?
C42 C41 H41 120.4 . . ?
C43 C42 C41 120.8(3) . . ?
C43 C42 Cl4 119.9(2) . . ?
C41 C42 Cl4 119.2(2) . . ?
C42 C43 C44 119.5(3) . . ?
C42 C43 H43 120.3 . . ?
C44 C43 H43 120.3 . . ?
C39 C44 C43 120.5(3) . . ?
C39 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
N7 C45 C29 178.8(3) . . ?
N9 C46 C31 177.1(3) . . ?
N10 C47 C31 178.1(3) . . ?
N1S C2S H2S1 109.5 . . ?
N1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
N1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
O1S C3S N1S 126.5(4) . . ?
O1S C3S H3S 116.7 . . ?
N1S C3S H3S 116.7 . . ?
C53 C52 H52A 109.5 . . ?
C53 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C53 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
N12 C53 C52 112.5(3) . . ?
N12 C53 H53A 109.1 . . ?
C52 C53 H53A 109.1 . . ?
N12 C53 H53B 109.1 . . ?
C52 C53 H53B 109.1 . . ?
H53A C53 H53B 107.8 . . ?
N12 C54 C55 109.9(3) . . ?
N12 C54 H54A 109.7 . . ?
C55 C54 H54A 109.7 . . ?
N12 C54 H54B 109.7 . . ?
C55 C54 H54B 109.7 . . ?
H54A C54 H54B 108.2 . . ?
C54 C55 H55A 109.5 . . ?
C54 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C54 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C7 N3 C8 115.1(2) . . ?
C7 N3 H3 122.4 . . ?
C8 N3 H3 122.4 . . ?
C3 N4 H4A 120.0 . . ?
C3 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C26 N5 C25 113.4(3) . . ?
C26 N5 H5A 108.5 . . ?
C25 N5 H5A 108.6 . . ?
C30 N8 H8A 120.0 . . ?
C30 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C3S N1S C1S 122.1(4) . . ?
C3S N1S C2S 120.7(4) . . ?
C1S N1S C2S 116.3(4) . . ?
C54 N12 C53 115.2(2) . . ?
C54 N12 H12A 108.2 . . ?
C53 N12 H12A 108.3 . . ?
C58 S2 C56 91.28(12) . . ?
C8 S1 C6 91.20(13) . . ?
C57 N11 C58 115.2(2) . . ?
C57 N11 H11A 122.4 . . ?
C58 N11 H11A 122.4 . . ?
O3 C58 N11 127.4(2) . . ?
O3 C58 S2 119.9(2) . . ?
N11 C58 S2 112.67(19) . . ?
O4 C57 N11 126.0(2) . . ?
O4 C57 C56 117.7(2) . . ?
N11 C57 C56 116.3(2) . . ?
C57 C56 C32 108.64(19) . . ?
C57 C56 C28 110.88(19) . . ?
C32 C56 C28 109.80(19) . . ?
C57 C56 S2 104.10(16) . . ?
C32 C56 S2 115.76(17) . . ?
C28 C56 S2 107.54(16) . . ?
N1S C1S H1S1 109.5 . . ?
N1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
N1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C6S N2S C4S 125.4(4) . . ?
C6S N2S C5S 119.6(4) . . ?
C4S N2S C5S 114.7(4) . . ?
N2S C6S O2S 122.2(4) . . ?
N2S C6S H6S 118.9 . . ?
O2S C6S H6S 118.9 . . ?
N2S C5S H5S1 109.5 . . ?
N2S C5S H5S2 109.5 . . ?
H5S1 C5S H5S2 109.5 . . ?
N2S C5S H5S3 109.5 . . ?
H5S1 C5S H5S3 109.5 . . ?
H5S2 C5S H5S3 109.5 . . ?
N2S C4S H4S1 109.5 . . ?
N2S C4S H4S2 109.5 . . ?
H4S1 C4S H4S2 109.5 . . ?
N2S C4S H4S3 109.5 . . ?
H4S1 C4S H4S3 109.5 . . ?
H4S2 C4S H4S3 109.5 . . ?
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 1.514(4) . ?
C1 C9 1.535(4) . ?
C1 C6 1.561(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.354(4) . ?
C2 C21 1.440(4) . ?
C3 N4 1.345(3) . ?
C3 C4 1.543(4) . ?
C4 C23 1.490(4) . ?
C4 C22 1.496(4) . ?
C4 C5 1.578(4) . ?
C5 C15 1.530(3) . ?
C5 C6 1.551(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.544(4) . ?
C6 S1 1.826(3) . ?
C7 O1 1.246(3) . ?
C7 N3 1.332(3) . ?
C8 O2 1.219(3) . ?
C8 N3 1.362(4) . ?
C8 S1 1.823(3) . ?
C9 C14 1.381(4) . ?
C9 C10 1.400(4) . ?
C10 C11 1.395(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(4) . ?
C12 Cl1 1.749(3) . ?
C13 C14 1.387(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.390(4) . ?
C15 C20 1.408(4) . ?
C16 C17 1.390(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(4) . ?
C18 Cl2 1.749(3) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 N1 1.148(4) . ?
C22 N2 1.144(4) . ?
C23 N6 1.149(4) . ?
C24 C25 1.489(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 N5 1.502(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 N5 1.495(4) . ?
C26 C27 1.501(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.522(3) . ?
C28 C39 1.539(4) . ?
C28 C56 1.558(3) . ?
C28 H28 0.9800 . ?
C29 C30 1.353(4) . ?
C29 C45 1.425(4) . ?
C30 N8 1.348(3) . ?
C30 C31 1.548(3) . ?
C31 C47 1.490(4) . ?
C31 C46 1.500(4) . ?
C31 C32 1.574(3) . ?
C32 C33 1.529(3) . ?
C32 C56 1.551(3) . ?
C32 H32 0.9800 . ?
C33 C34 1.397(4) . ?
C33 C38 1.396(4) . ?
C34 C35 1.388(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.375(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.386(4) . ?
C36 Cl3 1.754(3) . ?
C37 C38 1.381(4) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C44 1.389(4) . ?
C39 C40 1.390(4) . ?
C40 C41 1.375(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.391(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.375(4) . ?
C42 Cl4 1.750(3) . ?
C43 C44 1.390(4) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C45 N7 1.152(4) . ?
C46 N9 1.143(3) . ?
C47 N10 1.148(3) . ?
C2S N1S 1.452(5) . ?
C2S H2S1 0.9600 . ?
C2S H2S2 0.9600 . ?
C2S H2S3 0.9600 . ?
C3S O1S 1.242(4) . ?
C3S N1S 1.294(4) . ?
C3S H3S 0.9300 . ?
C52 C53 1.512(4) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 N12 1.512(4) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C54 N12 1.494(4) . ?
C54 C55 1.496(5) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
N3 H3 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5A 0.9000 . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N1S C1S 1.444(5) . ?
N12 H12A 0.9000 . ?
S2 C58 1.821(3) . ?
S2 C56 1.828(3) . ?
O4 C57 1.244(3) . ?
O3 C58 1.216(3) . ?
N11 C57 1.338(3) . ?
N11 C58 1.356(3) . ?
N11 H11A 0.8600 . ?
C57 C56 1.549(3) . ?
C1S H1S1 0.9600 . ?
C1S H1S2 0.9600 . ?
C1S H1S3 0.9600 . ?
O2S C6S 1.301(5) . ?
N2S C6S 1.291(5) . ?
N2S C4S 1.404(5) . ?
N2S C5S 1.491(5) . ?
C6S H6S 0.9300 . ?
C5S H5S1 0.9600 . ?
C5S H5S2 0.9600 . ?
C5S H5S3 0.9600 . ?
C4S H4S1 0.9600 . ?
C4S H4S2 0.9600 . ?
C4S H4S3 0.9600 . ?
