#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:54:16 +0300 (Thu, 05 May 2022) $
#$Revision: 275057 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158591.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_7158591
loop_
_publ_author_name
'Dai, Qing-Song'
'Li, Jun-Long'
'Wang, Qi-Wei'
'Yang, Si-Lin'
'Tao, Ying-Mao'
'He, Mei-Hao'
'Li, Qing-Zhu'
'Han, Bo'
'Zhang, Xiang'
_publ_section_title
;
 Sulphur ylide-mediated cyclopropanation and subsequent spirocyclopropane
 rearrangement reactions.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3486
_journal_page_last               3490
_journal_paper_doi               10.1039/d2ob00466f
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H22 N2 O3 S'
_chemical_formula_sum            'C30 H22 N2 O3 S'
_chemical_formula_weight         490.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-28 deposited with the CCDC.	2022-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.023(3)
_cell_length_b                   12.4076(16)
_cell_length_c                   18.781(3)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.395
_cell_measurement_theta_min      2.168
_cell_volume                     4898.9(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0676
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            43968
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_min         1.906
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0727 after correction.
The Ratio of minimum to maximum transmission is 0.9013.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       blcok
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 3274 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.46(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     651
_refine_ls_number_reflns         10630
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0422
_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)+(0.0421P)²+0.6828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                8787
_reflns_number_total             10630
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00466f2.cif
_cod_data_source_block           mo_ljl_0918_150k_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7158590--7158592.cif.'
_cod_original_cell_volume        4899.0(13)
_cod_database_code               7158591
_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_max   0.974
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C37(H37)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C39(H39), C40(H40),
 C44(H44), C45(H45), C46(H46), C47(H47), C51(H51), C52(H52), C54(H54), C55(H55),
  C56(H56), C57(H57), C58(H58), C59(H59), C60(H60)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C42(H42A,H42B,H42C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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
S1 S 0.63917(4) 0.53025(6) 0.47785(5) 0.02793(18) Uani 1 1 d . . . . .
S2 S 0.34223(4) 0.74183(6) 0.52866(5) 0.03032(18) Uani 1 1 d . . . . .
O1 O 0.57852(10) 0.39015(18) 0.59035(14) 0.0334(6) Uani 1 1 d . . . . .
O2 O 0.69179(11) 0.57967(18) 0.44250(14) 0.0353(6) Uani 1 1 d . . . . .
O3 O 0.59160(12) 0.59538(18) 0.51039(15) 0.0389(6) Uani 1 1 d . . . . .
O4 O 0.39438(13) 0.8038(2) 0.50382(16) 0.0467(7) Uani 1 1 d . . . . .
O5 O 0.41143(11) 0.6099(2) 0.41382(15) 0.0391(6) Uani 1 1 d . . . . .
O6 O 0.28739(12) 0.79433(17) 0.55693(14) 0.0349(6) Uani 1 1 d . . . . .
N1 N 0.67224(11) 0.45414(19) 0.54083(14) 0.0229(6) Uani 1 1 d . . . . .
N2 N 0.78817(14) 0.2653(2) 0.70952(15) 0.0317(7) Uani 1 1 d . . . . .
N3 N 0.31510(12) 0.6701(2) 0.46011(14) 0.0248(6) Uani 1 1 d . . . . .
N4 N 0.20642(13) 0.4739(2) 0.28896(15) 0.0275(6) Uani 1 1 d . . . . .
C1 C 0.5164(3) 0.2165(3) 0.2737(3) 0.0627(14) Uani 1 1 d . . . . .
H1A H 0.4710 0.2082 0.2842 0.094 Uiso 1 1 calc R U . . .
H1B H 0.5374 0.1462 0.2772 0.094 Uiso 1 1 calc R U . . .
H1C H 0.5216 0.2451 0.2255 0.094 Uiso 1 1 calc R U . . .
C2 C 0.5459(2) 0.2936(3) 0.3267(2) 0.0434(10) Uani 1 1 d . . . . .
C3 C 0.6107(2) 0.3149(3) 0.3227(2) 0.0406(9) Uani 1 1 d . . . . .
H3 H 0.6358 0.2789 0.2880 0.049 Uiso 1 1 calc R U . . .
C4 C 0.63934(18) 0.3875(3) 0.3683(2) 0.0345(8) Uani 1 1 d . . . . .
H4 H 0.6835 0.4026 0.3645 0.041 Uiso 1 1 calc R U . . .
C5 C 0.60248(16) 0.4381(3) 0.41970(19) 0.0287(7) Uani 1 1 d . . . . .
C6 C 0.74183(14) 0.4406(2) 0.55100(17) 0.0210(6) Uani 1 1 d . . . . .
H6 H 0.7625 0.5120 0.5596 0.025 Uiso 1 1 calc R U . . .
C7 C 0.74237(14) 0.3737(2) 0.61797(16) 0.0221(6) Uani 1 1 d . . . . .
C8 C 0.79584(16) 0.3304(2) 0.65469(18) 0.0264(7) Uani 1 1 d . . . . .
C9 C 0.86177(16) 0.3531(3) 0.63100(19) 0.0311(8) Uani 1 1 d . . . . .
C10 C 0.88587(19) 0.4573(3) 0.6331(3) 0.0492(11) Uani 1 1 d . . . . .
H10 H 0.8600 0.5149 0.6497 0.059 Uiso 1 1 calc R U . . .
C11 C 0.9476(2) 0.4770(4) 0.6110(3) 0.0656(14) Uani 1 1 d . . . . .
H11 H 0.9641 0.5483 0.6123 0.079 Uiso 1 1 calc R U . . .
C12 C 0.9851(2) 0.3932(5) 0.5871(3) 0.0650(14) Uani 1 1 d . . . . .
H12 H 1.0280 0.4062 0.5736 0.078 Uiso 1 1 calc R U . . .
C13 C 0.51061(19) 0.3449(3) 0.3785(2) 0.0447(10) Uani 1 1 d . . . . .
H13 H 0.4664 0.3301 0.3820 0.054 Uiso 1 1 calc R U . . .
C14 C 0.53786(17) 0.4177(3) 0.4259(2) 0.0374(9) Uani 1 1 d . . . . .
H14 H 0.5130 0.4524 0.4614 0.045 Uiso 1 1 calc R U . . .
C15 C 0.63606(15) 0.3967(2) 0.59079(18) 0.0245(7) Uani 1 1 d . . . . .
C16 C 0.68241(15) 0.3475(2) 0.63947(17) 0.0228(6) Uani 1 1 d . . . . .
C17 C 0.77362(14) 0.3827(2) 0.48895(16) 0.0217(6) Uani 1 1 d . . . . .
C18 C 0.75065(15) 0.2831(2) 0.46672(18) 0.0274(7) Uani 1 1 d . . . . .
H18 H 0.7155 0.2513 0.4905 0.033 Uiso 1 1 calc R U . . .
C19 C 0.77874(17) 0.2304(3) 0.41022(19) 0.0332(8) Uani 1 1 d . . . . .
H19 H 0.7626 0.1628 0.3948 0.040 Uiso 1 1 calc R U . . .
C20 C 0.83025(17) 0.2760(3) 0.3761(2) 0.0377(9) Uani 1 1 d . . . . .
H20 H 0.8493 0.2403 0.3368 0.045 Uiso 1 1 calc R U . . .
C21 C 0.85415(17) 0.3737(3) 0.3993(2) 0.0364(8) Uani 1 1 d . . . . .
H21 H 0.8901 0.4045 0.3763 0.044 Uiso 1 1 calc R U . . .
C22 C 0.82584(15) 0.4269(3) 0.45573(19) 0.0289(7) Uani 1 1 d . . . . .
H22 H 0.8425 0.4939 0.4716 0.035 Uiso 1 1 calc R U . . .
C23 C 0.9605(2) 0.2909(4) 0.5829(3) 0.0603(13) Uani 1 1 d . . . . .
H23 H 0.9858 0.2337 0.5648 0.072 Uiso 1 1 calc R U . . .
C24 C 0.89905(18) 0.2709(3) 0.6050(3) 0.0464(10) Uani 1 1 d . . . . .
H24 H 0.8823 0.1999 0.6022 0.056 Uiso 1 1 calc R U . . .
C25 C 0.72769(17) 0.2413(3) 0.73290(18) 0.0309(8) Uani 1 1 d . . . . .
C26 C 0.67206(17) 0.2806(2) 0.69929(18) 0.0283(7) Uani 1 1 d . . . . .
C27 C 0.61153(19) 0.2517(3) 0.7262(2) 0.0377(9) Uani 1 1 d . . . . .
H27 H 0.5739 0.2765 0.7035 0.045 Uiso 1 1 calc R U . . .
C28 C 0.6079(2) 0.1873(3) 0.7855(2) 0.0506(12) Uani 1 1 d . . . . .
H28 H 0.5674 0.1686 0.8043 0.061 Uiso 1 1 calc R U . . .
C29 C 0.6629(2) 0.1490(3) 0.8185(2) 0.0510(12) Uani 1 1 d . . . . .
H29 H 0.6592 0.1047 0.8596 0.061 Uiso 1 1 calc R U . . .
C30 C 0.7214(2) 0.1737(3) 0.7932(2) 0.0431(10) Uani 1 1 d . . . . .
H30 H 0.7582 0.1457 0.8159 0.052 Uiso 1 1 calc R U . . .
C31 C 0.0097(2) 0.5846(5) 0.4206(3) 0.0643(14) Uani 1 1 d . . . . .
H31 H -0.0318 0.5938 0.4397 0.077 Uiso 1 1 calc R U . . .
C32 C 0.0348(2) 0.4833(4) 0.4155(3) 0.0586(12) Uani 1 1 d . . . . .
H32 H 0.0108 0.4227 0.4306 0.070 Uiso 1 1 calc R U . . .
C33 C 0.09490(17) 0.4696(3) 0.3885(2) 0.0407(9) Uani 1 1 d . . . . .
H33 H 0.1122 0.3991 0.3847 0.049 Uiso 1 1 calc R U . . .
C34 C 0.13064(16) 0.5576(3) 0.36675(19) 0.0298(7) Uani 1 1 d . . . . .
C35 C 0.19672(15) 0.5398(2) 0.34288(17) 0.0243(6) Uani 1 1 d . . . . .
C36 C 0.24869(15) 0.5867(2) 0.38049(17) 0.0228(6) Uani 1 1 d . . . . .
C37 C 0.24606(14) 0.6535(2) 0.44760(17) 0.0234(6) Uani 1 1 d . . . . .
H37 H 0.2245 0.7239 0.4382 0.028 Uiso 1 1 calc R U . . .
C38 C 0.36952(15) 0.6464(3) 0.59014(19) 0.0285(7) Uani 1 1 d . . . . .
C39 C 0.43097(17) 0.6076(3) 0.5846(2) 0.0375(8) Uani 1 1 d . . . . .
H39 H 0.4589 0.6338 0.5488 0.045 Uiso 1 1 calc R U . . .
C40 C 0.45099(18) 0.5292(3) 0.6325(2) 0.0409(9) Uani 1 1 d . . . . .
H40 H 0.4929 0.5010 0.6288 0.049 Uiso 1 1 calc R U . . .
C41 C 0.41126(19) 0.4916(3) 0.6854(2) 0.0389(9) Uani 1 1 d . . . . .
C42 C 0.4339(2) 0.4113(3) 0.7403(3) 0.0552(12) Uani 1 1 d . . . . .
H42A H 0.4724 0.3754 0.7229 0.083 Uiso 1 1 calc R U . . .
H42B H 0.4006 0.3574 0.7485 0.083 Uiso 1 1 calc R U . . .
H42C H 0.4433 0.4488 0.7849 0.083 Uiso 1 1 calc R U . . .
C43 C 0.26761(16) 0.4539(2) 0.26700(17) 0.0276(7) Uani 1 1 d . . . . .
C44 C 0.27575(19) 0.3857(3) 0.20745(19) 0.0341(8) Uani 1 1 d . . . . .
H44 H 0.2397 0.3543 0.1850 0.041 Uiso 1 1 calc R U . . .
C45 C 0.3357(2) 0.3649(3) 0.1820(2) 0.0415(9) Uani 1 1 d . . . . .
H45 H 0.3410 0.3198 0.1415 0.050 Uiso 1 1 calc R U . . .
C46 C 0.38887(19) 0.4091(3) 0.2151(2) 0.0398(9) Uani 1 1 d . . . . .
H46 H 0.4300 0.3940 0.1967 0.048 Uiso 1 1 calc R U . . .
C47 C 0.38291(18) 0.4745(3) 0.2738(2) 0.0347(8) Uani 1 1 d . . . . .
H47 H 0.4197 0.5034 0.2962 0.042 Uiso 1 1 calc R U . . .
C48 C 0.32215(16) 0.4981(2) 0.30040(18) 0.0277(7) Uani 1 1 d . . . . .
C49 C 0.30932(15) 0.5649(2) 0.36052(17) 0.0240(7) Uani 1 1 d . . . . .
C50 C 0.35416(16) 0.6152(3) 0.41156(18) 0.0272(7) Uani 1 1 d . . . . .
C51 C 0.0438(2) 0.6740(4) 0.3983(3) 0.0599(14) Uani 1 1 d . . . . .
H51 H 0.0257 0.7440 0.4014 0.072 Uiso 1 1 calc R U . . .
C52 C 0.10507(18) 0.6601(3) 0.3712(2) 0.0436(10) Uani 1 1 d . . . . .
H52 H 0.1291 0.7207 0.3560 0.052 Uiso 1 1 calc R U . . .
C53 C 0.21345(15) 0.5947(2) 0.50827(17) 0.0232(6) Uani 1 1 d . . . . .
C54 C 0.23544(16) 0.4942(2) 0.53004(19) 0.0287(7) Uani 1 1 d . . . . .
H54 H 0.2702 0.4616 0.5059 0.034 Uiso 1 1 calc R U . . .
C55 C 0.20698(18) 0.4418(3) 0.5865(2) 0.0359(8) Uani 1 1 d . . . . .
H55 H 0.2228 0.3739 0.6019 0.043 Uiso 1 1 calc R U . . .
C56 C 0.15561(19) 0.4878(3) 0.6206(2) 0.0415(9) Uani 1 1 d . . . . .
H56 H 0.1358 0.4515 0.6592 0.050 Uiso 1 1 calc R U . . .
C57 C 0.13308(18) 0.5866(3) 0.5984(2) 0.0402(9) Uani 1 1 d . . . . .
H57 H 0.0978 0.6182 0.6221 0.048 Uiso 1 1 calc R U . . .
C58 C 0.16158(16) 0.6405(3) 0.54187(19) 0.0296(7) Uani 1 1 d . . . . .
H58 H 0.1455 0.7082 0.5265 0.036 Uiso 1 1 calc R U . . .
C59 C 0.32804(16) 0.6081(3) 0.64131(19) 0.0304(7) Uani 1 1 d . . . . .
H59 H 0.2857 0.6347 0.6438 0.037 Uiso 1 1 calc R U . . .
C60 C 0.34890(18) 0.5306(3) 0.6888(2) 0.0363(8) Uani 1 1 d . . . . .
H60 H 0.3206 0.5037 0.7240 0.044 Uiso 1 1 calc R U . . .
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
O2 S1 N1 104.49(14) . . ?
O2 S1 C5 109.27(16) . . ?
O3 S1 O2 119.99(15) . . ?
O3 S1 N1 108.07(15) . . ?
O3 S1 C5 109.11(16) . . ?
N1 S1 C5 104.80(14) . . ?
O4 S2 O6 119.98(16) . . ?
O4 S2 N3 107.46(16) . . ?
O4 S2 C38 109.28(17) . . ?
O6 S2 N3 104.77(14) . . ?
O6 S2 C38 109.16(16) . . ?
N3 S2 C38 105.12(14) . . ?
C6 N1 S1 124.5(2) . . ?
C15 N1 S1 122.5(2) . . ?
C15 N1 C6 113.0(2) . . ?
C8 N2 C25 119.6(3) . . ?
C37 N3 S2 122.1(2) . . ?
C50 N3 S2 124.1(2) . . ?
C50 N3 C37 113.7(3) . . ?
C35 N4 C43 119.2(3) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 119.2(4) . . ?
C13 C2 C1 122.4(4) . . ?
C13 C2 C3 118.4(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.9(4) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 S1 118.8(3) . . ?
C14 C5 S1 119.7(3) . . ?
C14 C5 C4 121.5(3) . . ?
N1 C6 H6 110.5 . . ?
N1 C6 C7 100.2(2) . . ?
N1 C6 C17 112.8(3) . . ?
C7 C6 H6 110.5 . . ?
C7 C6 C17 112.1(2) . . ?
C17 C6 H6 110.5 . . ?
C8 C7 C6 128.2(3) . . ?
C16 C7 C6 111.8(3) . . ?
C16 C7 C8 119.8(3) . . ?
N2 C8 C7 120.9(3) . . ?
N2 C8 C9 117.7(3) . . ?
C7 C8 C9 121.4(3) . . ?
C10 C9 C8 120.6(3) . . ?
C24 C9 C8 119.9(3) . . ?
C24 C9 C10 119.5(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(5) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C23 C12 C11 119.9(4) . . ?
C23 C12 H12 120.0 . . ?
C2 C13 H13 119.0 . . ?
C2 C13 C14 122.0(4) . . ?
C14 C13 H13 119.0 . . ?
C5 C14 C13 117.9(4) . . ?
C5 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
O1 C15 N1 124.8(3) . . ?
O1 C15 C16 129.7(3) . . ?
N1 C15 C16 105.5(3) . . ?
C7 C16 C15 109.3(3) . . ?
C7 C16 C26 121.2(3) . . ?
C26 C16 C15 129.5(3) . . ?
C18 C17 C6 119.7(3) . . ?
C22 C17 C6 120.6(3) . . ?
C22 C17 C18 119.6(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.9(3) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 120.1(3) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C12 C23 H23 119.9 . . ?
C12 C23 C24 120.2(4) . . ?
C24 C23 H23 119.9 . . ?
C9 C24 C23 120.5(4) . . ?
C9 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
N2 C25 C26 123.1(3) . . ?
N2 C25 C30 118.0(3) . . ?
C30 C25 C26 118.9(3) . . ?
C16 C26 C25 115.4(3) . . ?
C16 C26 C27 124.8(3) . . ?
C27 C26 C25 119.7(3) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 C26 119.2(4) . . ?
C28 C27 H27 120.4 . . ?
C27 C28 H28 119.6 . . ?
C27 C28 C29 120.8(4) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 119.4 . . ?
C30 C29 C28 121.3(4) . . ?
C30 C29 H29 119.4 . . ?
C25 C30 H30 119.9 . . ?
C29 C30 C25 120.1(4) . . ?
C29 C30 H30 119.9 . . ?
C32 C31 H31 119.5 . . ?
C32 C31 C51 120.9(4) . . ?
C51 C31 H31 119.5 . . ?
C31 C32 H32 120.1 . . ?
C31 C32 C33 119.8(4) . . ?
C33 C32 H32 120.1 . . ?
C32 C33 H33 119.7 . . ?
C32 C33 C34 120.6(4) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 C35 118.7(3) . . ?
C52 C34 C33 119.7(3) . . ?
C52 C34 C35 121.5(3) . . ?
N4 C35 C34 118.2(3) . . ?
N4 C35 C36 121.0(3) . . ?
C36 C35 C34 120.6(3) . . ?
C35 C36 C37 127.6(3) . . ?
C49 C36 C35 120.2(3) . . ?
C49 C36 C37 112.0(3) . . ?
N3 C37 C36 99.9(2) . . ?
N3 C37 H37 110.4 . . ?
N3 C37 C53 113.0(3) . . ?
C36 C37 H37 110.4 . . ?
C36 C37 C53 112.3(2) . . ?
C53 C37 H37 110.4 . . ?
C39 C38 S2 119.5(3) . . ?
C59 C38 S2 119.0(3) . . ?
C59 C38 C39 121.5(3) . . ?
C38 C39 H39 120.7 . . ?
C38 C39 C40 118.6(4) . . ?
C40 C39 H39 120.7 . . ?
C39 C40 H40 119.3 . . ?
C41 C40 C39 121.3(3) . . ?
C41 C40 H40 119.3 . . ?
C40 C41 C42 121.6(4) . . ?
C40 C41 C60 118.9(4) . . ?
C60 C41 C42 119.5(4) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N4 C43 C44 117.3(3) . . ?
N4 C43 C48 123.7(3) . . ?
C44 C43 C48 119.0(3) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 C43 119.9(4) . . ?
C45 C44 H44 120.0 . . ?
C44 C45 H45 119.7 . . ?
C44 C45 C46 120.5(3) . . ?
C46 C45 H45 119.7 . . ?
C45 C46 H46 119.4 . . ?
C47 C46 C45 121.2(3) . . ?
C47 C46 H46 119.4 . . ?
C46 C47 H47 120.3 . . ?
C46 C47 C48 119.5(4) . . ?
C48 C47 H47 120.3 . . ?
C43 C48 C49 115.0(3) . . ?
C47 C48 C43 119.9(3) . . ?
C47 C48 C49 125.1(3) . . ?
C36 C49 C48 120.8(3) . . ?
C36 C49 C50 109.6(3) . . ?
C48 C49 C50 129.5(3) . . ?
O5 C50 N3 126.0(3) . . ?
O5 C50 C49 129.4(3) . . ?
N3 C50 C49 104.6(3) . . ?
C31 C51 H51 120.4 . . ?
C31 C51 C52 119.2(4) . . ?
C52 C51 H51 120.4 . . ?
C34 C52 C51 119.7(4) . . ?
C34 C52 H52 120.2 . . ?
C51 C52 H52 120.2 . . ?
C54 C53 C37 120.1(3) . . ?
C58 C53 C37 120.2(3) . . ?
C58 C53 C54 119.7(3) . . ?
C53 C54 H54 119.9 . . ?
C55 C54 C53 120.3(3) . . ?
C55 C54 H54 119.9 . . ?
C54 C55 H55 120.0 . . ?
C56 C55 C54 120.0(3) . . ?
C56 C55 H55 120.0 . . ?
C55 C56 H56 120.1 . . ?
C57 C56 C55 119.8(3) . . ?
C57 C56 H56 120.1 . . ?
C56 C57 H57 119.7 . . ?
C56 C57 C58 120.7(3) . . ?
C58 C57 H57 119.7 . . ?
C53 C58 C57 119.4(3) . . ?
C53 C58 H58 120.3 . . ?
C57 C58 H58 120.3 . . ?
C38 C59 H59 120.4 . . ?
C38 C59 C60 119.2(3) . . ?
C60 C59 H59 120.4 . . ?
C41 C60 H60 119.7 . . ?
C59 C60 C41 120.6(4) . . ?
C59 C60 H60 119.7 . . ?
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
S1 O2 1.429(2) . ?
S1 O3 1.424(3) . ?
S1 N1 1.666(3) . ?
S1 C5 1.759(3) . ?
S2 O4 1.418(3) . ?
S2 O6 1.427(3) . ?
S2 N3 1.666(3) . ?
S2 C38 1.750(3) . ?
O1 C15 1.212(4) . ?
O5 C50 1.206(4) . ?
N1 C6 1.485(4) . ?
N1 C15 1.402(4) . ?
N2 C8 1.319(4) . ?
N2 C25 1.378(5) . ?
N3 C37 1.485(4) . ?
N3 C50 1.403(4) . ?
N4 C35 1.317(4) . ?
N4 C43 1.373(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.513(5) . ?
C2 C3 1.391(6) . ?
C2 C13 1.380(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(5) . ?
C5 C14 1.387(5) . ?
C6 H6 1.0000 . ?
C6 C7 1.507(4) . ?
C6 C17 1.523(4) . ?
C7 C8 1.424(4) . ?
C7 C16 1.363(4) . ?
C8 C9 1.483(5) . ?
C9 C10 1.389(5) . ?
C9 C24 1.376(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(7) . ?
C12 H12 0.9500 . ?
C12 C23 1.373(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.469(5) . ?
C16 C26 1.414(4) . ?
C17 C18 1.391(4) . ?
C17 C22 1.376(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.378(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.416(5) . ?
C25 C30 1.415(5) . ?
C26 C27 1.416(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.373(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.396(7) . ?
C29 H29 0.9500 . ?
C29 C30 1.353(6) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C31 C32 1.367(7) . ?
C31 C51 1.386(7) . ?
C32 H32 0.9500 . ?
C32 C33 1.371(6) . ?
C33 H33 0.9500 . ?
C33 C34 1.387(5) . ?
C34 C35 1.477(5) . ?
C34 C52 1.383(5) . ?
C35 C36 1.425(4) . ?
C36 C37 1.509(4) . ?
C36 C49 1.356(4) . ?
C37 H37 1.0000 . ?
C37 C53 1.516(4) . ?
C38 C39 1.383(5) . ?
C38 C59 1.382(5) . ?
C39 H39 0.9500 . ?
C39 C40 1.390(6) . ?
C40 H40 0.9500 . ?
C40 C41 1.379(6) . ?
C41 C42 1.510(5) . ?
C41 C60 1.399(5) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.413(5) . ?
C43 C48 1.417(5) . ?
C44 H44 0.9500 . ?
C44 C45 1.373(5) . ?
C45 H45 0.9500 . ?
C45 C46 1.391(6) . ?
C46 H46 0.9500 . ?
C46 C47 1.375(5) . ?
C47 H47 0.9500 . ?
C47 C48 1.402(5) . ?
C48 C49 1.427(5) . ?
C49 C50 1.482(5) . ?
C51 H51 0.9500 . ?
C51 C52 1.396(6) . ?
C52 H52 0.9500 . ?
C53 C54 1.391(4) . ?
C53 C58 1.382(5) . ?
C54 H54 0.9500 . ?
C54 C55 1.381(5) . ?
C55 H55 0.9500 . ?
C55 C56 1.379(5) . ?
C56 H56 0.9500 . ?
C56 C57 1.379(5) . ?
C57 H57 0.9500 . ?
C57 C58 1.391(5) . ?
C58 H58 0.9500 . ?
C59 H59 0.9500 . ?
C59 C60 1.383(5) . ?
C60 H60 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C6 C7 175.0(2) . . . . ?
S1 N1 C6 C17 -65.7(3) . . . . ?
S1 N1 C15 O1 5.5(4) . . . . ?
S1 N1 C15 C16 -175.8(2) . . . . ?
S1 C5 C14 C13 179.5(3) . . . . ?
S2 N3 C37 C36 179.3(2) . . . . ?
S2 N3 C37 C53 -61.1(3) . . . . ?
S2 N3 C50 O5 2.2(5) . . . . ?
S2 N3 C50 C49 -179.4(2) . . . . ?
S2 C38 C39 C40 -177.9(3) . . . . ?
S2 C38 C59 C60 178.3(3) . . . . ?
O1 C15 C16 C7 177.6(3) . . . . ?
O1 C15 C16 C26 -0.9(5) . . . . ?
O2 S1 N1 C6 -3.3(3) . . . . ?
O2 S1 N1 C15 175.9(2) . . . . ?
O2 S1 C5 C4 29.5(3) . . . . ?
O2 S1 C5 C14 -150.3(3) . . . . ?
O3 S1 N1 C6 -132.1(2) . . . . ?
O3 S1 N1 C15 47.1(3) . . . . ?
O3 S1 C5 C4 162.5(3) . . . . ?
O3 S1 C5 C14 -17.4(3) . . . . ?
O4 S2 N3 C37 -140.1(2) . . . . ?
O4 S2 N3 C50 43.6(3) . . . . ?
O4 S2 C38 C39 -28.7(3) . . . . ?
O4 S2 C38 C59 154.2(3) . . . . ?
O6 S2 N3 C37 -11.4(3) . . . . ?
O6 S2 N3 C50 172.3(2) . . . . ?
O6 S2 C38 C39 -161.7(3) . . . . ?
O6 S2 C38 C59 21.2(3) . . . . ?
N1 S1 C5 C4 -82.0(3) . . . . ?
N1 S1 C5 C14 98.2(3) . . . . ?
N1 C6 C7 C8 177.8(3) . . . . ?
N1 C6 C7 C16 3.6(3) . . . . ?
N1 C6 C17 C18 -53.9(4) . . . . ?
N1 C6 C17 C22 127.7(3) . . . . ?
N1 C15 C16 C7 -1.0(3) . . . . ?
N1 C15 C16 C26 -179.5(3) . . . . ?
N2 C8 C9 C10 -117.8(4) . . . . ?
N2 C8 C9 C24 63.8(5) . . . . ?
N2 C25 C26 C16 -0.3(4) . . . . ?
N2 C25 C26 C27 179.5(3) . . . . ?
N2 C25 C30 C29 179.2(3) . . . . ?
N3 S2 C38 C39 86.4(3) . . . . ?
N3 S2 C38 C59 -90.8(3) . . . . ?
N3 C37 C53 C54 -56.3(4) . . . . ?
N3 C37 C53 C58 124.1(3) . . . . ?
N4 C35 C36 C37 -172.9(3) . . . . ?
N4 C35 C36 C49 0.8(4) . . . . ?
N4 C43 C44 C45 178.4(3) . . . . ?
N4 C43 C48 C47 -179.2(3) . . . . ?
N4 C43 C48 C49 1.1(4) . . . . ?
C1 C2 C3 C4 177.7(4) . . . . ?
C1 C2 C13 C14 -178.4(4) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C2 C13 C14 C5 0.1(6) . . . . ?
C3 C2 C13 C14 0.8(6) . . . . ?
C3 C4 C5 S1 179.8(3) . . . . ?
C3 C4 C5 C14 -0.3(5) . . . . ?
C4 C5 C14 C13 -0.3(5) . . . . ?
C5 S1 N1 C6 111.6(2) . . . . ?
C5 S1 N1 C15 -69.2(3) . . . . ?
C6 N1 C15 O1 -175.2(3) . . . . ?
C6 N1 C15 C16 3.5(3) . . . . ?
C6 C7 C8 N2 -174.0(3) . . . . ?
C6 C7 C8 C9 3.4(5) . . . . ?
C6 C7 C16 C15 -1.8(3) . . . . ?
C6 C7 C16 C26 176.9(3) . . . . ?
C6 C17 C18 C19 179.5(3) . . . . ?
C6 C17 C22 C21 -179.8(3) . . . . ?
C7 C6 C17 C18 58.3(4) . . . . ?
C7 C6 C17 C22 -120.1(3) . . . . ?
C7 C8 C9 C10 64.6(5) . . . . ?
C7 C8 C9 C24 -113.7(4) . . . . ?
C7 C16 C26 C25 -1.8(4) . . . . ?
C7 C16 C26 C27 178.4(3) . . . . ?
C8 N2 C25 C26 2.1(5) . . . . ?
C8 N2 C25 C30 -178.2(3) . . . . ?
C8 C7 C16 C15 -176.6(3) . . . . ?
C8 C7 C16 C26 2.1(4) . . . . ?
C8 C9 C10 C11 179.8(4) . . . . ?
C8 C9 C24 C23 -179.9(4) . . . . ?
C9 C10 C11 C12 -0.2(8) . . . . ?
C10 C9 C24 C23 1.8(6) . . . . ?
C10 C11 C12 C23 2.3(8) . . . . ?
C11 C12 C23 C24 -2.4(8) . . . . ?
C12 C23 C24 C9 0.3(7) . . . . ?
C13 C2 C3 C4 -1.5(6) . . . . ?
C15 N1 C6 C7 -4.3(3) . . . . ?
C15 N1 C6 C17 115.0(3) . . . . ?
C15 C16 C26 C25 176.6(3) . . . . ?
C15 C16 C26 C27 -3.3(5) . . . . ?
C16 C7 C8 N2 -0.2(5) . . . . ?
C16 C7 C8 C9 177.3(3) . . . . ?
C16 C26 C27 C28 -179.0(3) . . . . ?
C17 C6 C7 C8 58.0(4) . . . . ?
C17 C6 C7 C16 -116.3(3) . . . . ?
C17 C18 C19 C20 0.8(5) . . . . ?
C18 C17 C22 C21 1.8(5) . . . . ?
C18 C19 C20 C21 0.9(6) . . . . ?
C19 C20 C21 C22 -1.2(6) . . . . ?
C20 C21 C22 C17 -0.2(6) . . . . ?
C22 C17 C18 C19 -2.1(5) . . . . ?
C24 C9 C10 C11 -1.9(7) . . . . ?
C25 N2 C8 C7 -1.9(4) . . . . ?
C25 N2 C8 C9 -179.4(3) . . . . ?
C25 C26 C27 C28 1.2(5) . . . . ?
C26 C25 C30 C29 -1.0(5) . . . . ?
C26 C27 C28 C29 -1.1(6) . . . . ?
C27 C28 C29 C30 -0.1(6) . . . . ?
C28 C29 C30 C25 1.2(6) . . . . ?
C30 C25 C26 C16 180.0(3) . . . . ?
C30 C25 C26 C27 -0.2(5) . . . . ?
C31 C32 C33 C34 0.5(7) . . . . ?
C31 C51 C52 C34 0.3(6) . . . . ?
C32 C31 C51 C52 -0.9(7) . . . . ?
C32 C33 C34 C35 175.7(4) . . . . ?
C32 C33 C34 C52 -1.1(6) . . . . ?
C33 C34 C35 N4 58.4(4) . . . . ?
C33 C34 C35 C36 -117.3(4) . . . . ?
C33 C34 C52 C51 0.6(6) . . . . ?
C34 C35 C36 C37 2.6(5) . . . . ?
C34 C35 C36 C49 176.3(3) . . . . ?
C35 N4 C43 C44 -177.9(3) . . . . ?
C35 N4 C43 C48 1.7(5) . . . . ?
C35 C34 C52 C51 -176.0(4) . . . . ?
C35 C36 C37 N3 176.7(3) . . . . ?
C35 C36 C37 C53 56.7(4) . . . . ?
C35 C36 C49 C48 2.1(4) . . . . ?
C35 C36 C49 C50 -175.0(3) . . . . ?
C36 C37 C53 C54 55.8(4) . . . . ?
C36 C37 C53 C58 -123.8(3) . . . . ?
C36 C49 C50 O5 176.1(3) . . . . ?
C36 C49 C50 N3 -2.1(3) . . . . ?
C37 N3 C50 O5 -174.4(3) . . . . ?
C37 N3 C50 C49 4.0(3) . . . . ?
C37 C36 C49 C48 176.8(3) . . . . ?
C37 C36 C49 C50 -0.4(3) . . . . ?
C37 C53 C54 C55 178.3(3) . . . . ?
C37 C53 C58 C57 -178.6(3) . . . . ?
C38 S2 N3 C37 103.6(2) . . . . ?
C38 S2 N3 C50 -72.7(3) . . . . ?
C38 C39 C40 C41 -1.0(5) . . . . ?
C38 C59 C60 C41 0.3(5) . . . . ?
C39 C38 C59 C60 1.2(5) . . . . ?
C39 C40 C41 C42 -176.4(4) . . . . ?
C39 C40 C41 C60 2.4(5) . . . . ?
C40 C41 C60 C59 -2.1(5) . . . . ?
C42 C41 C60 C59 176.8(3) . . . . ?
C43 N4 C35 C34 -178.3(3) . . . . ?
C43 N4 C35 C36 -2.7(4) . . . . ?
C43 C44 C45 C46 1.0(5) . . . . ?
C43 C48 C49 C36 -2.9(4) . . . . ?
C43 C48 C49 C50 173.6(3) . . . . ?
C44 C43 C48 C47 0.5(5) . . . . ?
C44 C43 C48 C49 -179.3(3) . . . . ?
C44 C45 C46 C47 0.1(5) . . . . ?
C45 C46 C47 C48 -0.8(5) . . . . ?
C46 C47 C48 C43 0.5(5) . . . . ?
C46 C47 C48 C49 -179.7(3) . . . . ?
C47 C48 C49 C36 177.3(3) . . . . ?
C47 C48 C49 C50 -6.2(5) . . . . ?
C48 C43 C44 C45 -1.2(5) . . . . ?
C48 C49 C50 O5 -0.7(6) . . . . ?
C48 C49 C50 N3 -179.0(3) . . . . ?
C49 C36 C37 N3 2.6(3) . . . . ?
C49 C36 C37 C53 -117.4(3) . . . . ?
C50 N3 C37 C36 -4.1(3) . . . . ?
C50 N3 C37 C53 115.5(3) . . . . ?
C51 C31 C32 C33 0.5(7) . . . . ?
C52 C34 C35 N4 -125.0(4) . . . . ?
C52 C34 C35 C36 59.4(5) . . . . ?
C53 C54 C55 C56 1.5(5) . . . . ?
C54 C53 C58 C57 1.8(5) . . . . ?
C54 C55 C56 C57 -0.5(6) . . . . ?
C55 C56 C57 C58 0.2(6) . . . . ?
C56 C57 C58 C53 -0.8(6) . . . . ?
C58 C53 C54 C55 -2.1(5) . . . . ?
C59 C38 C39 C40 -0.8(5) . . . . ?
