#------------------------------------------------------------------------------
#$Date: 2022-09-21 03:32:42 +0300 (Wed, 21 Sep 2022) $
#$Revision: 278020 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/88/7158887.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_7158887
loop_
_publ_author_name
'Meng, Xiangrui'
'Guo, Weisi'
'Nan, Guang-Ming'
'Li, Ming'
_publ_section_title
;
 Synthesis of pyrrole disulfides via umpolung of β-ketothioamides
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01506D
_journal_year                    2022
_chemical_formula_moiety         'C40 H34 N4 O6 S2, C H2 Cl2'
_chemical_formula_sum            'C41 H36 Cl2 N4 O6 S2'
_chemical_formula_weight         815.76
_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   mixed
_audit_creation_date             2015-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-04-18 deposited with the CCDC.	2022-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                102.494(7)
_cell_angle_beta                 94.881(5)
_cell_angle_gamma                91.629(5)
_cell_formula_units_Z            2
_cell_length_a                   8.200(3)
_cell_length_b                   14.629(5)
_cell_length_c                   17.002(6)
_cell_measurement_reflns_used    6790
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4830
_cell_measurement_theta_min      1.2321
_cell_volume                     1981.7(12)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 39.9565
	          2theta: -19.8344
scan:
	Number of images: 264
	           Slice: -77.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 39.9565
	          2theta: -19.8344
scan:
	Number of images: 240
	           Slice: -110.0000 - 10.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 39.9565
	          2theta: -19.8344
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0870
_diffrn_orient_matrix_UB_12      0.0454
_diffrn_orient_matrix_UB_13      -0.0734
_diffrn_orient_matrix_UB_21      0.0024
_diffrn_orient_matrix_UB_22      0.0608
_diffrn_orient_matrix_UB_23      0.0348
_diffrn_orient_matrix_UB_31      0.0454
_diffrn_orient_matrix_UB_32      -0.0088
_diffrn_orient_matrix_UB_33      0.0390
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21520
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         1.427
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       rod
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.929
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         8909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0772
_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)+(0.0551P)²+1.9572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.1797
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7251
_reflns_number_total             8909
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01506d2.cif
_cod_data_source_block           mx4339
_cod_original_cell_volume        1981.8(11)
_cod_database_code               7158887
_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.
;
_diffrn_number_total             8910
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H41C)=Sof(H41D)=Sof(Cl2A)=Sof(Cl1A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(H41A)=Sof(H41B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C33(H33A,H33B), C41(H41A,H41B), C41(H41C,H41D)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C36(H36),
  C37(H37), C38(H38), C39(H39), C40(H40)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C34(H34A,H34B,H34C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
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
S1 S 0.40078(9) 0.30119(5) 0.66354(5) 0.03073(19) Uani 1 1 d . . . . .
S2 S 0.42872(9) 0.42895(5) 0.62633(4) 0.02841(18) Uani 1 1 d . . . . .
O1 O 0.7596(3) 0.33690(16) 0.78551(14) 0.0456(6) Uani 1 1 d . . . . .
O2 O 1.0108(3) 0.05669(17) 0.58141(14) 0.0425(6) Uani 1 1 d . . . . .
O3 O 1.0229(3) 0.15258(15) 0.70454(13) 0.0343(5) Uani 1 1 d . . . . .
O4 O 0.3396(3) 0.64635(16) 0.77690(14) 0.0374(5) Uani 1 1 d . . . . .
O5 O 0.9398(3) 0.70618(17) 0.86880(14) 0.0414(6) Uani 1 1 d . . . . .
O6 O 0.6738(3) 0.71741(16) 0.89255(13) 0.0353(5) Uani 1 1 d . . . . .
N1 N 0.5637(3) 0.18526(17) 0.54730(15) 0.0303(6) Uani 1 1 d . . . . .
N2 N 0.7392(4) 0.0835(2) 0.47004(18) 0.0417(7) Uani 1 1 d . . . . .
N3 N 0.7512(3) 0.49122(18) 0.67189(14) 0.0278(5) Uani 1 1 d . . . . .
N4 N 1.0049(3) 0.5705(2) 0.72699(19) 0.0413(7) Uani 1 1 d . . . . .
C1 C 0.5620(4) 0.2355(2) 0.62813(18) 0.0287(6) Uani 1 1 d . . . . .
C2 C 0.6971(4) 0.2134(2) 0.67181(18) 0.0294(6) Uani 1 1 d . . . . .
C3 C 0.7871(4) 0.1495(2) 0.61786(18) 0.0307(6) Uani 1 1 d . . . . .
C4 C 0.7009(4) 0.1355(2) 0.54107(18) 0.0320(7) Uani 1 1 d . . . . .
C5 C 0.7397(4) 0.2526(2) 0.76055(19) 0.0333(7) Uani 1 1 d . . . . .
C6 C 0.7544(4) 0.1871(2) 0.81646(18) 0.0347(7) Uani 1 1 d . . . . .
C7 C 0.8228(4) 0.2219(3) 0.89578(19) 0.0413(8) Uani 1 1 d . . . . .
H7 H 0.8569 0.2849 0.9125 0.050 Uiso 1 1 calc R . . . .
C8 C 0.8401(5) 0.1635(3) 0.9498(2) 0.0485(9) Uani 1 1 d . . . . .
H8 H 0.8865 0.1872 1.0024 0.058 Uiso 1 1 calc R . . . .
C9 C 0.7893(5) 0.0713(3) 0.9260(2) 0.0554(10) Uani 1 1 d . . . . .
H9 H 0.8013 0.0322 0.9623 0.066 Uiso 1 1 calc R . . . .
C10 C 0.7195(6) 0.0359(3) 0.8473(2) 0.0547(10) Uani 1 1 d . . . . .
H10 H 0.6839 -0.0268 0.8312 0.066 Uiso 1 1 calc R . . . .
C11 C 0.7030(5) 0.0936(2) 0.7929(2) 0.0413(8) Uani 1 1 d . . . . .
H11 H 0.6571 0.0695 0.7403 0.050 Uiso 1 1 calc R . . . .
C12 C 0.9479(4) 0.1144(2) 0.63104(18) 0.0320(7) Uani 1 1 d . . . . .
C13 C 1.1806(4) 0.1164(2) 0.7244(2) 0.0365(7) Uani 1 1 d . . . . .
H13A H 1.2579 0.1275 0.6870 0.044 Uiso 1 1 calc R . . . .
H13B H 1.1694 0.0495 0.7213 0.044 Uiso 1 1 calc R . . . .
C14 C 1.2395(5) 0.1671(3) 0.8090(2) 0.0530(10) Uani 1 1 d . . . . .
H14A H 1.2481 0.2332 0.8115 0.080 Uiso 1 1 calc GR . . . .
H14B H 1.3450 0.1458 0.8240 0.080 Uiso 1 1 calc GR . . . .
H14C H 1.1632 0.1545 0.8455 0.080 Uiso 1 1 calc GR . . . .
C15 C 0.4495(4) 0.1908(2) 0.47931(18) 0.0292(6) Uani 1 1 d . . . . .
C16 C 0.3166(5) 0.1289(3) 0.4570(2) 0.0494(9) Uani 1 1 d . . . . .
H16 H 0.2952 0.0845 0.4870 0.059 Uiso 1 1 calc R . . . .
C17 C 0.2141(5) 0.1340(3) 0.3885(3) 0.0608(12) Uani 1 1 d . . . . .
H17 H 0.1232 0.0926 0.3728 0.073 Uiso 1 1 calc R . . . .
C18 C 0.2454(5) 0.1993(3) 0.3440(2) 0.0474(9) Uani 1 1 d . . . . .
H18 H 0.1782 0.2008 0.2974 0.057 Uiso 1 1 calc R . . . .
C19 C 0.3755(5) 0.2620(3) 0.3686(2) 0.0553(10) Uani 1 1 d . . . . .
H19 H 0.3948 0.3077 0.3397 0.066 Uiso 1 1 calc R . . . .
C20 C 0.4788(5) 0.2580(3) 0.4362(2) 0.0479(9) Uani 1 1 d . . . . .
H20 H 0.5680 0.3006 0.4525 0.058 Uiso 1 1 calc R . . . .
C21 C 0.5847(3) 0.4954(2) 0.68883(17) 0.0247(6) Uani 1 1 d . . . . .
C22 C 0.5787(3) 0.5613(2) 0.75922(16) 0.0256(6) Uani 1 1 d . . . . .
C23 C 0.7403(4) 0.5998(2) 0.78626(17) 0.0268(6) Uani 1 1 d . . . . .
C24 C 0.8432(4) 0.5540(2) 0.73043(17) 0.0288(6) Uani 1 1 d . . . . .
C25 C 0.4237(4) 0.5872(2) 0.79885(17) 0.0267(6) Uani 1 1 d . . . . .
C26 C 0.3771(4) 0.5383(2) 0.86169(17) 0.0291(6) Uani 1 1 d . . . . .
C27 C 0.2549(4) 0.5745(2) 0.9105(2) 0.0359(7) Uani 1 1 d . . . . .
H27 H 0.2084 0.6303 0.9050 0.043 Uiso 1 1 calc R . . . .
C28 C 0.2033(5) 0.5276(3) 0.9666(2) 0.0467(9) Uani 1 1 d . . . . .
H28 H 0.1225 0.5519 0.9993 0.056 Uiso 1 1 calc R . . . .
C29 C 0.2717(5) 0.4445(3) 0.9741(2) 0.0492(9) Uani 1 1 d . . . . .
H29 H 0.2349 0.4123 1.0113 0.059 Uiso 1 1 calc R . . . .
C30 C 0.3939(5) 0.4086(2) 0.9273(2) 0.0429(8) Uani 1 1 d . . . . .
H30 H 0.4397 0.3527 0.9332 0.052 Uiso 1 1 calc R . . . .
C31 C 0.4486(4) 0.4560(2) 0.87128(18) 0.0323(7) Uani 1 1 d . . . . .
H31 H 0.5326 0.4327 0.8404 0.039 Uiso 1 1 calc R . . . .
C32 C 0.7969(4) 0.6773(2) 0.85164(18) 0.0291(6) Uani 1 1 d . . . . .
C33 C 0.7208(5) 0.7987(3) 0.9567(2) 0.0453(9) Uani 1 1 d . . . . .
H33A H 0.7913 0.8419 0.9375 0.054 Uiso 1 1 calc R . . . .
H33B H 0.7799 0.7800 1.0021 0.054 Uiso 1 1 calc R . . . .
C34 C 0.5670(5) 0.8444(3) 0.9820(3) 0.0573(11) Uani 1 1 d . . . . .
H34A H 0.5109 0.8638 0.9369 0.086 Uiso 1 1 calc GR . . . .
H34B H 0.5940 0.8981 1.0254 0.086 Uiso 1 1 calc GR . . . .
H34C H 0.4975 0.8006 0.9999 0.086 Uiso 1 1 calc GR . . . .
C35 C 0.8138(3) 0.4391(2) 0.60025(17) 0.0277(6) Uani 1 1 d . . . . .
C36 C 0.9236(4) 0.3706(2) 0.6062(2) 0.0344(7) Uani 1 1 d . . . . .
H36 H 0.9537 0.3565 0.6560 0.041 Uiso 1 1 calc R . . . .
C37 C 0.9888(4) 0.3229(2) 0.5369(2) 0.0389(8) Uani 1 1 d . . . . .
H37 H 1.0637 0.2771 0.5403 0.047 Uiso 1 1 calc R . . . .
C38 C 0.9424(4) 0.3437(2) 0.4632(2) 0.0401(8) Uani 1 1 d . . . . .
H38 H 0.9859 0.3116 0.4169 0.048 Uiso 1 1 calc R . . . .
C39 C 0.8317(4) 0.4119(2) 0.45761(19) 0.0368(7) Uani 1 1 d . . . . .
H39 H 0.7996 0.4249 0.4075 0.044 Uiso 1 1 calc R . . . .
C40 C 0.7682(4) 0.4610(2) 0.52666(18) 0.0311(6) Uani 1 1 d . . . . .
H40 H 0.6958 0.5082 0.5235 0.037 Uiso 1 1 calc R . . . .
Cl1 Cl 0.0766(3) 0.92503(19) 0.83841(19) 0.0704(7) Uani 0.699(4) 1 d . . P A 1
Cl2 Cl 0.3605(3) 0.87920(17) 0.74800(15) 0.0894(9) Uani 0.699(4) 1 d . . P A 1
C41 C 0.2017(7) 0.8394(3) 0.7992(4) 0.0761(14) Uani 1 1 d . . . . .
H41A H 0.1362 0.7898 0.7617 0.091 Uiso 0.699(4) 1 calc R . P A 1
H41B H 0.2507 0.8130 0.8427 0.091 Uiso 0.699(4) 1 calc R . P A 1
H41C H 0.3028 0.8171 0.8205 0.091 Uiso 0.301(4) 1 calc R . P A 2
H41D H 0.1143 0.7940 0.8009 0.091 Uiso 0.301(4) 1 calc R . P A 2
Cl2A Cl 0.2171(7) 0.8432(3) 0.7066(3) 0.0793(19) Uani 0.301(4) 1 d . . P A 2
Cl1A Cl 0.1617(17) 0.9477(5) 0.8640(4) 0.125(4) Uani 0.301(4) 1 d . . P A 2
H4A H 1.058(5) 0.534(3) 0.693(2) 0.050(11) Uiso 1 1 d . . . . .
H4B H 1.060(5) 0.608(3) 0.768(3) 0.053(12) Uiso 1 1 d . . . . .
H2A H 0.826(5) 0.055(3) 0.465(2) 0.040(10) Uiso 1 1 d . . . . .
H2B H 0.686(6) 0.088(3) 0.427(3) 0.071(15) Uiso 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'
Cl Cl 0.1484 0.1585 '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
C1 S1 S2 105.60(11) . . ?
C21 S2 S1 107.86(10) . . ?
C12 O3 C13 116.2(2) . . ?
C32 O6 C33 115.7(2) . . ?
C1 N1 C15 127.1(2) . . ?
C4 N1 C1 108.8(2) . . ?
C4 N1 C15 123.8(2) . . ?
C4 N2 H2A 123(3) . . ?
C4 N2 H2B 119(3) . . ?
H2A N2 H2B 117(4) . . ?
C21 N3 C35 126.8(2) . . ?
C24 N3 C21 109.0(2) . . ?
C24 N3 C35 123.8(2) . . ?
C24 N4 H4A 121(3) . . ?
C24 N4 H4B 118(3) . . ?
H4A N4 H4B 119(4) . . ?
N1 C1 S1 123.6(2) . . ?
C2 C1 S1 128.0(2) . . ?
C2 C1 N1 107.9(2) . . ?
C1 C2 C3 107.9(3) . . ?
C1 C2 C5 124.3(3) . . ?
C3 C2 C5 127.8(3) . . ?
C2 C3 C12 129.9(3) . . ?
C4 C3 C2 106.7(3) . . ?
C4 C3 C12 122.7(3) . . ?
N1 C4 C3 108.6(3) . . ?
N2 C4 N1 122.3(3) . . ?
N2 C4 C3 129.1(3) . . ?
O1 C5 C2 119.6(3) . . ?
O1 C5 C6 121.3(3) . . ?
C6 C5 C2 119.0(3) . . ?
C7 C6 C5 118.4(3) . . ?
C11 C6 C5 122.6(3) . . ?
C11 C6 C7 119.0(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.5(4) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.9(4) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 H11 119.9 . . ?
C10 C11 C6 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
O2 C12 O3 122.7(3) . . ?
O2 C12 C3 124.5(3) . . ?
O3 C12 C3 112.8(3) . . ?
O3 C13 H13A 110.3 . . ?
O3 C13 H13B 110.3 . . ?
O3 C13 C14 107.0(3) . . ?
H13A C13 H13B 108.6 . . ?
C14 C13 H13A 110.3 . . ?
C14 C13 H13B 110.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N1 120.7(3) . . ?
C16 C15 C20 120.7(3) . . ?
C20 C15 N1 118.6(3) . . ?
C15 C16 H16 120.7 . . ?
C15 C16 C17 118.6(4) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.5(4) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 119.8(3) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
N3 C21 S2 122.9(2) . . ?
C22 C21 S2 129.9(2) . . ?
C22 C21 N3 107.1(2) . . ?
C21 C22 C23 108.5(2) . . ?
C21 C22 C25 124.2(3) . . ?
C23 C22 C25 127.3(3) . . ?
C22 C23 C32 130.2(3) . . ?
C24 C23 C22 106.7(2) . . ?
C24 C23 C32 122.8(3) . . ?
N3 C24 C23 108.7(3) . . ?
N4 C24 N3 122.2(3) . . ?
N4 C24 C23 128.8(3) . . ?
O4 C25 C22 119.1(3) . . ?
O4 C25 C26 122.3(3) . . ?
C26 C25 C22 118.6(2) . . ?
C27 C26 C25 119.0(3) . . ?
C31 C26 C25 121.3(3) . . ?
C31 C26 C27 119.7(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.1(3) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.1 . . ?
C27 C28 C29 119.8(3) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 119.6 . . ?
C30 C29 C28 120.8(3) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.9(3) . . ?
C31 C30 H30 120.1 . . ?
C26 C31 C30 119.7(3) . . ?
C26 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
O5 C32 O6 122.4(3) . . ?
O5 C32 C23 124.9(3) . . ?
O6 C32 C23 112.7(3) . . ?
O6 C33 H33A 110.2 . . ?
O6 C33 H33B 110.2 . . ?
O6 C33 C34 107.4(3) . . ?
H33A C33 H33B 108.5 . . ?
C34 C33 H33A 110.2 . . ?
C34 C33 H33B 110.2 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 N3 119.7(3) . . ?
C36 C35 C40 121.0(3) . . ?
C40 C35 N3 119.2(3) . . ?
C35 C36 H36 120.3 . . ?
C35 C36 C37 119.4(3) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 119.9(3) . . ?
C38 C37 H37 120.0 . . ?
C37 C38 H38 119.8 . . ?
C37 C38 C39 120.4(3) . . ?
C39 C38 H38 119.8 . . ?
C38 C39 H39 120.0 . . ?
C38 C39 C40 120.1(3) . . ?
C40 C39 H39 120.0 . . ?
C35 C40 C39 119.2(3) . . ?
C35 C40 H40 120.4 . . ?
C39 C40 H40 120.4 . . ?
Cl1 C41 Cl2 113.7(3) . . ?
Cl1 C41 H41A 108.8 . . ?
Cl1 C41 H41B 108.8 . . ?
Cl2 C41 H41A 108.8 . . ?
Cl2 C41 H41B 108.8 . . ?
H41A C41 H41B 107.7 . . ?
H41C C41 H41D 107.5 . . ?
Cl2A C41 H41C 108.4 . . ?
Cl2A C41 H41D 108.4 . . ?
Cl2A C41 Cl1A 115.4(4) . . ?
Cl1A C41 H41C 108.4 . . ?
Cl1A C41 H41D 108.4 . . ?
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 S2 2.1114(12) . ?
S1 C1 1.730(3) . ?
S2 C21 1.721(3) . ?
O1 C5 1.215(4) . ?
O2 C12 1.217(4) . ?
O3 C12 1.342(4) . ?
O3 C13 1.452(4) . ?
O4 C25 1.222(4) . ?
O5 C32 1.223(4) . ?
O6 C32 1.351(4) . ?
O6 C33 1.447(4) . ?
N1 C1 1.413(4) . ?
N1 C4 1.357(4) . ?
N1 C15 1.442(4) . ?
N2 C4 1.348(4) . ?
N2 H2A 0.84(4) . ?
N2 H2B 0.84(5) . ?
N3 C21 1.419(4) . ?
N3 C24 1.356(4) . ?
N3 C35 1.434(4) . ?
N4 C24 1.350(4) . ?
N4 H4A 0.86(4) . ?
N4 H4B 0.88(4) . ?
C1 C2 1.367(4) . ?
C2 C3 1.429(4) . ?
C2 C5 1.501(4) . ?
C3 C4 1.402(4) . ?
C3 C12 1.446(4) . ?
C5 C6 1.490(5) . ?
C6 C7 1.397(4) . ?
C6 C11 1.382(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.364(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.393(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(5) . ?
C11 H11 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.499(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.369(5) . ?
C15 C20 1.376(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.394(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.362(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(4) . ?
C22 C23 1.423(4) . ?
C22 C25 1.509(4) . ?
C23 C24 1.398(4) . ?
C23 C32 1.440(4) . ?
C25 C26 1.477(4) . ?
C26 C27 1.398(4) . ?
C26 C31 1.389(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.376(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.380(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.378(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.389(5) . ?
C31 H31 0.9300 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.497(5) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.379(4) . ?
C35 C40 1.382(4) . ?
C36 H36 0.9300 . ?
C36 C37 1.390(4) . ?
C37 H37 0.9300 . ?
C37 C38 1.378(5) . ?
C38 H38 0.9300 . ?
C38 C39 1.381(5) . ?
C39 H39 0.9300 . ?
C39 C40 1.388(4) . ?
C40 H40 0.9300 . ?
Cl1 C41 1.701(6) . ?
Cl2 C41 1.778(6) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 H41C 0.9700 . ?
C41 H41D 0.9700 . ?
C41 Cl2A 1.603(7) . ?
C41 Cl1A 1.779(9) . ?
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
N4 H4B O4 0.88(4) 2.33(4) 2.917(4) 125(3) 1_655
N4 H4B O5 0.88(4) 2.29(4) 2.871(4) 124(3) .
N2 H2A O2 0.84(4) 2.20(4) 2.990(4) 158(3) 2_756
N2 H2A O2 0.84(4) 2.38(4) 2.890(4) 120(3) .
N2 H2B Cl2A 0.84(5) 2.84(5) 3.442(5) 131(4) 2_666
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 S2 C21 N3 89.9(2) . . . . ?
S1 S2 C21 C22 -92.3(3) . . . . ?
S1 C1 C2 C3 173.7(2) . . . . ?
S1 C1 C2 C5 -7.3(5) . . . . ?
S2 S1 C1 N1 -79.6(3) . . . . ?
S2 S1 C1 C2 108.6(3) . . . . ?
S2 C21 C22 C23 -177.3(2) . . . . ?
S2 C21 C22 C25 2.2(5) . . . . ?
O1 C5 C6 C7 -12.4(5) . . . . ?
O1 C5 C6 C11 167.5(3) . . . . ?
O4 C25 C26 C27 -14.8(4) . . . . ?
O4 C25 C26 C31 163.2(3) . . . . ?
N1 C1 C2 C3 0.9(3) . . . . ?
N1 C1 C2 C5 179.9(3) . . . . ?
N1 C15 C16 C17 -176.9(3) . . . . ?
N1 C15 C20 C19 177.0(3) . . . . ?
N3 C21 C22 C23 0.8(3) . . . . ?
N3 C21 C22 C25 -179.7(3) . . . . ?
N3 C35 C36 C37 -177.4(3) . . . . ?
N3 C35 C40 C39 178.6(3) . . . . ?
C1 N1 C4 N2 -177.3(3) . . . . ?
C1 N1 C4 C3 2.3(4) . . . . ?
C1 N1 C15 C16 -94.2(4) . . . . ?
C1 N1 C15 C20 87.3(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C2 C3 C12 171.3(3) . . . . ?
C1 C2 C5 O1 -58.6(5) . . . . ?
C1 C2 C5 C6 120.6(3) . . . . ?
C2 C3 C4 N1 -1.7(4) . . . . ?
C2 C3 C4 N2 177.8(3) . . . . ?
C2 C3 C12 O2 176.9(3) . . . . ?
C2 C3 C12 O3 -3.5(5) . . . . ?
C2 C5 C6 C7 168.4(3) . . . . ?
C2 C5 C6 C11 -11.7(5) . . . . ?
C3 C2 C5 O1 120.2(4) . . . . ?
C3 C2 C5 C6 -60.7(4) . . . . ?
C4 N1 C1 S1 -175.2(2) . . . . ?
C4 N1 C1 C2 -2.0(4) . . . . ?
C4 N1 C15 C16 92.1(4) . . . . ?
C4 N1 C15 C20 -86.5(4) . . . . ?
C4 C3 C12 O2 -13.6(5) . . . . ?
C4 C3 C12 O3 166.0(3) . . . . ?
C5 C2 C3 C4 -178.5(3) . . . . ?
C5 C2 C3 C12 -7.7(6) . . . . ?
C5 C6 C7 C8 -179.5(3) . . . . ?
C5 C6 C11 C10 -180.0(3) . . . . ?
C6 C7 C8 C9 -0.5(6) . . . . ?
C7 C6 C11 C10 -0.1(5) . . . . ?
C7 C8 C9 C10 -0.1(6) . . . . ?
C8 C9 C10 C11 0.6(6) . . . . ?
C9 C10 C11 C6 -0.5(6) . . . . ?
C11 C6 C7 C8 0.6(5) . . . . ?
C12 O3 C13 C14 -178.8(3) . . . . ?
C12 C3 C4 N1 -173.3(3) . . . . ?
C12 C3 C4 N2 6.2(6) . . . . ?
C13 O3 C12 O2 -4.2(5) . . . . ?
C13 O3 C12 C3 176.1(3) . . . . ?
C15 N1 C1 S1 10.3(4) . . . . ?
C15 N1 C1 C2 -176.5(3) . . . . ?
C15 N1 C4 N2 -2.5(5) . . . . ?
C15 N1 C4 C3 177.0(3) . . . . ?
C15 C16 C17 C18 0.1(7) . . . . ?
C16 C15 C20 C19 -1.5(6) . . . . ?
C16 C17 C18 C19 -2.1(7) . . . . ?
C17 C18 C19 C20 2.3(7) . . . . ?
C18 C19 C20 C15 -0.5(7) . . . . ?
C20 C15 C16 C17 1.6(6) . . . . ?
C21 N3 C24 N4 -175.0(3) . . . . ?
C21 N3 C24 C23 0.1(3) . . . . ?
C21 N3 C35 C36 -119.5(3) . . . . ?
C21 N3 C35 C40 63.2(4) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C21 C22 C23 C32 172.7(3) . . . . ?
C21 C22 C25 O4 -85.6(4) . . . . ?
C21 C22 C25 C26 93.0(3) . . . . ?
C22 C23 C24 N3 0.4(3) . . . . ?
C22 C23 C24 N4 175.0(3) . . . . ?
C22 C23 C32 O5 -178.3(3) . . . . ?
C22 C23 C32 O6 0.6(5) . . . . ?
C22 C25 C26 C27 166.7(3) . . . . ?
C22 C25 C26 C31 -15.4(4) . . . . ?
C23 C22 C25 O4 93.8(4) . . . . ?
C23 C22 C25 C26 -87.6(4) . . . . ?
C24 N3 C21 S2 177.7(2) . . . . ?
C24 N3 C21 C22 -0.6(3) . . . . ?
C24 N3 C35 C36 68.9(4) . . . . ?
C24 N3 C35 C40 -108.4(3) . . . . ?
C24 C23 C32 O5 -5.8(5) . . . . ?
C24 C23 C32 O6 173.1(3) . . . . ?
C25 C22 C23 C24 179.8(3) . . . . ?
C25 C22 C23 C32 -6.8(5) . . . . ?
C25 C26 C27 C28 176.6(3) . . . . ?
C25 C26 C31 C30 -175.7(3) . . . . ?
C26 C27 C28 C29 -0.4(5) . . . . ?
C27 C26 C31 C30 2.3(5) . . . . ?
C27 C28 C29 C30 1.4(6) . . . . ?
C28 C29 C30 C31 -0.5(6) . . . . ?
C29 C30 C31 C26 -1.4(5) . . . . ?
C31 C26 C27 C28 -1.4(5) . . . . ?
C32 O6 C33 C34 168.0(3) . . . . ?
C32 C23 C24 N3 -173.6(3) . . . . ?
C32 C23 C24 N4 1.0(5) . . . . ?
C33 O6 C32 O5 1.8(4) . . . . ?
C33 O6 C32 C23 -177.2(3) . . . . ?
C35 N3 C21 S2 5.0(4) . . . . ?
C35 N3 C21 C22 -173.2(3) . . . . ?
C35 N3 C24 N4 -2.0(5) . . . . ?
C35 N3 C24 C23 173.0(3) . . . . ?
C35 C36 C37 C38 -0.6(5) . . . . ?
C36 C35 C40 C39 1.3(5) . . . . ?
C36 C37 C38 C39 0.2(5) . . . . ?
C37 C38 C39 C40 1.0(5) . . . . ?
C38 C39 C40 C35 -1.7(5) . . . . ?
C40 C35 C36 C37 -0.2(5) . . . . ?
