# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'J Aube'
'Michal Szostak'

_publ_contact_author_name        'J Aube'
_publ_contact_author_email       JAUBE@KU.EDU

_publ_section_title              
;
Synthesis and rearrangement of a bridged thioamide
;

# Attachment 'Thioamide_SI_X-ray_comp_3a.cif'

#====================
data_k35g
_database_code_depnum_ccdc_archive 'CCDC 745512'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20.50 H30.50 Cl1.50 I N S'
_chemical_formula_weight         503.09

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'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6036(5)
_cell_length_b                   12.2354(6)
_cell_length_c                   18.6396(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.5200(10)
_cell_angle_gamma                90.00
_cell_volume                     2183.41(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9815
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      30.37

_exptl_crystal_description       'Rectangular parallelepiped'
_exptl_crystal_colour            Yellow-brown
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1020
_exptl_absorpt_coefficient_mu    1.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            26417
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         30.51
_reflns_number_total             12766
_reflns_number_gt                12378
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections except those that were flagged
by the user for being in the beamstop. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0539P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(12)
_refine_ls_number_reflns         12766
_refine_ls_number_parameters     460
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I1 I 0.22294(3) 0.13843(2) 0.522828(15) 0.02045(7) Uani 1 1 d . . .
I2 I 0.78338(3) 0.99286(2) -0.030282(15) 0.02228(7) Uani 1 1 d . . .
S1 S 0.05684(11) 0.43067(9) 0.30625(6) 0.0177(2) Uani 1 1 d . . .
N1 N 0.0634(4) 0.4192(3) 0.44432(19) 0.0154(7) Uani 1 1 d . . .
C1 C 0.1925(4) 0.4578(4) 0.2469(2) 0.0182(8) Uani 1 1 d . . .
H1A H 0.1499 0.4633 0.1969 0.022 Uiso 1 1 calc R . .
H1B H 0.2362 0.5291 0.2598 0.022 Uiso 1 1 calc R . .
C2 C 0.3057(5) 0.3695(4) 0.2502(2) 0.0190(8) Uani 1 1 d . . .
H2A H 0.3779 0.3898 0.2175 0.023 Uiso 1 1 calc R . .
H2B H 0.2636 0.2994 0.2331 0.023 Uiso 1 1 calc R . .
C3 C 0.3755(4) 0.3539(3) 0.3270(2) 0.0154(7) Uani 1 1 d . . .
H3 H 0.3091 0.3121 0.3553 0.018 Uiso 1 1 calc R . .
C4 C 0.3973(4) 0.4668(3) 0.3623(2) 0.0117(7) Uani 1 1 d . . .
H4A H 0.4100 0.5208 0.3237 0.014 Uiso 1 1 calc R . .
H4B H 0.4856 0.4646 0.3935 0.014 Uiso 1 1 calc R . .
C5 C 0.2786(4) 0.5101(3) 0.4087(2) 0.0115(7) Uani 1 1 d . . .
C6 C 0.1365(4) 0.4529(3) 0.3929(2) 0.0144(8) Uani 1 1 d . . .
C7 C 0.3294(4) 0.4862(4) 0.4876(2) 0.0158(7) Uani 1 1 d . . .
H7A H 0.3530 0.4078 0.4931 0.019 Uiso 1 1 calc R . .
H7B H 0.4149 0.5292 0.5010 0.019 Uiso 1 1 calc R . .
C8 C 0.2179(4) 0.5154(4) 0.5371(2) 0.0156(8) Uani 1 1 d . . .
H8A H 0.2554 0.5079 0.5879 0.019 Uiso 1 1 calc R . .
H8B H 0.1882 0.5922 0.5290 0.019 Uiso 1 1 calc R . .
C9 C 0.0947(4) 0.4399(4) 0.5222(2) 0.0180(8) Uani 1 1 d . . .
H9A H 0.1145 0.3695 0.5471 0.022 Uiso 1 1 calc R . .
H9B H 0.0116 0.4725 0.5420 0.022 Uiso 1 1 calc R . .
C10 C 0.5137(4) 0.2871(4) 0.3277(2) 0.0165(8) Uani 1 1 d . . .
C11 C 0.4864(5) 0.1799(4) 0.2861(3) 0.0296(11) Uani 1 1 d . . .
H11A H 0.5693 0.1332 0.2923 0.044 Uiso 1 1 calc R . .
H11B H 0.4656 0.1960 0.2349 0.044 Uiso 1 1 calc R . .
H11C H 0.4067 0.1421 0.3046 0.044 Uiso 1 1 calc R . .
C12 C 0.5610(5) 0.2577(4) 0.4062(2) 0.0218(9) Uani 1 1 d . . .
H12A H 0.6452 0.2123 0.4072 0.033 Uiso 1 1 calc R . .
H12B H 0.4865 0.2172 0.4275 0.033 Uiso 1 1 calc R . .
H12C H 0.5815 0.3248 0.4337 0.033 Uiso 1 1 calc R . .
C13 C 0.6307(4) 0.3508(4) 0.2955(2) 0.0208(9) Uani 1 1 d . . .
H13A H 0.7144 0.3050 0.2960 0.031 Uiso 1 1 calc R . .
H13B H 0.6517 0.4169 0.3241 0.031 Uiso 1 1 calc R . .
H13C H 0.6009 0.3714 0.2458 0.031 Uiso 1 1 calc R . .
C14 C -0.0698(4) 0.3605(4) 0.4305(3) 0.0213(9) Uani 1 1 d . . .
H14A H -0.0624 0.3087 0.3908 0.032 Uiso 1 1 calc R . .
H14B H -0.1447 0.4130 0.4175 0.032 Uiso 1 1 calc R . .
H14C H -0.0911 0.3205 0.4739 0.032 Uiso 1 1 calc R . .
C15 C 0.2622(4) 0.6336(4) 0.39768(19) 0.0142(7) Uani 1 1 d . . .
C16 C 0.3831(4) 0.6985(3) 0.4088(2) 0.0157(8) Uani 1 1 d . . .
H16 H 0.4704 0.6645 0.4217 0.019 Uiso 1 1 calc R . .
C17 C 0.3767(5) 0.8114(3) 0.4011(2) 0.0183(8) Uani 1 1 d . . .
H17 H 0.4589 0.8541 0.4097 0.022 Uiso 1 1 calc R . .
C18 C 0.2509(5) 0.8615(4) 0.3808(2) 0.0213(9) Uani 1 1 d . . .
H18 H 0.2464 0.9386 0.3751 0.026 Uiso 1 1 calc R . .
C19 C 0.1299(5) 0.7978(4) 0.3687(2) 0.0225(10) Uani 1 1 d . . .
H19 H 0.0434 0.8319 0.3538 0.027 Uiso 1 1 calc R . .
C20 C 0.1357(5) 0.6861(4) 0.3782(2) 0.0178(8) Uani 1 1 d . . .
H20 H 0.0524 0.6442 0.3715 0.021 Uiso 1 1 calc R . .
S2 S 0.90753(11) 0.68157(9) 0.19977(6) 0.0165(2) Uani 1 1 d . . .
N2 N 0.8989(4) 0.7000(3) 0.06179(18) 0.0139(6) Uani 1 1 d . . .
C21 C 0.7747(4) 0.6463(4) 0.2589(2) 0.0170(8) Uani 1 1 d . . .
H21A H 0.7370 0.5731 0.2458 0.020 Uiso 1 1 calc R . .
H21B H 0.8174 0.6425 0.3090 0.020 Uiso 1 1 calc R . .
C22 C 0.6549(4) 0.7287(3) 0.2553(2) 0.0164(8) Uani 1 1 d . . .
H22A H 0.6908 0.8001 0.2736 0.020 Uiso 1 1 calc R . .
H22B H 0.5833 0.7038 0.2871 0.020 Uiso 1 1 calc R . .
C23 C 0.5860(4) 0.7438(3) 0.1781(2) 0.0140(7) Uani 1 1 d . . .
H23 H 0.6527 0.7869 0.1507 0.017 Uiso 1 1 calc R . .
C24 C 0.5718(4) 0.6303(3) 0.14263(19) 0.0124(7) Uani 1 1 d . . .
H24A H 0.4838 0.6289 0.1112 0.015 Uiso 1 1 calc R . .
H24B H 0.5631 0.5753 0.1809 0.015 Uiso 1 1 calc R . .
C25 C 0.6947(4) 0.5944(3) 0.0965(2) 0.0138(8) Uani 1 1 d . . .
C26 C 0.8297(4) 0.6610(3) 0.1133(2) 0.0135(8) Uani 1 1 d . . .
C27 C 0.6404(4) 0.6189(3) 0.0169(2) 0.0143(8) Uani 1 1 d . . .
H27A H 0.5588 0.5720 0.0030 0.017 Uiso 1 1 calc R . .
H27B H 0.6102 0.6961 0.0125 0.017 Uiso 1 1 calc R . .
C28 C 0.7551(5) 0.5974(4) -0.0334(2) 0.0183(9) Uani 1 1 d . . .
H28A H 0.7911 0.5220 -0.0265 0.022 Uiso 1 1 calc R . .
H28B H 0.7175 0.6056 -0.0841 0.022 Uiso 1 1 calc R . .
C29 C 0.8714(4) 0.6792(4) -0.0161(2) 0.0149(8) Uani 1 1 d . . .
H29A H 0.9580 0.6516 -0.0353 0.018 Uiso 1 1 calc R . .
H29B H 0.8465 0.7490 -0.0407 0.018 Uiso 1 1 calc R . .
C30 C 0.4462(4) 0.8083(3) 0.1742(2) 0.0154(8) Uani 1 1 d . . .
C31 C 0.4686(5) 0.9170(4) 0.2159(3) 0.0256(10) Uani 1 1 d . . .
H31A H 0.3818 0.9595 0.2118 0.038 Uiso 1 1 calc R . .
H31B H 0.5430 0.9590 0.1955 0.038 Uiso 1 1 calc R . .
H31C H 0.4952 0.9014 0.2667 0.038 Uiso 1 1 calc R . .
C32 C 0.4009(5) 0.8346(4) 0.0960(2) 0.0209(9) Uani 1 1 d . . .
H32A H 0.3882 0.7665 0.0686 0.031 Uiso 1 1 calc R . .
H32B H 0.4728 0.8792 0.0755 0.031 Uiso 1 1 calc R . .
H32C H 0.3126 0.8751 0.0935 0.031 Uiso 1 1 calc R . .
C33 C 0.3294(4) 0.7422(4) 0.2064(2) 0.0181(8) Uani 1 1 d . . .
H33A H 0.3106 0.6757 0.1780 0.027 Uiso 1 1 calc R . .
H33B H 0.2444 0.7866 0.2055 0.027 Uiso 1 1 calc R . .
H33C H 0.3590 0.7223 0.2562 0.027 Uiso 1 1 calc R . .
C34 C 1.0252(4) 0.7683(4) 0.0769(3) 0.0221(9) Uani 1 1 d . . .
H34A H 1.0088 0.8210 0.1149 0.033 Uiso 1 1 calc R . .
H34B H 1.0456 0.8076 0.0331 0.033 Uiso 1 1 calc R . .
H34C H 1.1046 0.7215 0.0926 0.033 Uiso 1 1 calc R . .
C35 C 0.7230(4) 0.4717(3) 0.1048(2) 0.0134(8) Uani 1 1 d . . .
C36 C 0.6111(5) 0.3985(4) 0.0971(2) 0.0168(8) Uani 1 1 d . . .
H36 H 0.5182 0.4252 0.0897 0.020 Uiso 1 1 calc R . .
C37 C 0.6356(5) 0.2872(4) 0.1005(2) 0.0190(8) Uani 1 1 d . . .
H37 H 0.5587 0.2383 0.0937 0.023 Uiso 1 1 calc R . .
C38 C 0.7676(5) 0.2453(4) 0.1132(2) 0.0223(9) Uani 1 1 d . . .
H38 H 0.7824 0.1687 0.1164 0.027 Uiso 1 1 calc R . .
C39 C 0.8790(5) 0.3176(4) 0.1214(2) 0.0211(9) Uani 1 1 d . . .
H39 H 0.9710 0.2898 0.1304 0.025 Uiso 1 1 calc R . .
C40 C 0.8583(4) 0.4302(4) 0.1166(2) 0.0156(8) Uani 1 1 d . . .
H40 H 0.9360 0.4785 0.1214 0.019 Uiso 1 1 calc R . .
Cl1S Cl -0.15804(14) 0.00407(14) 0.25458(7) 0.0411(3) Uani 1 1 d . . .
Cl2S Cl 0.09347(13) 0.07207(12) 0.19249(7) 0.0346(3) Uani 1 1 d . . .
Cl3S Cl 0.05999(12) 0.11711(9) 0.34207(6) 0.0245(2) Uani 1 1 d . . .
C1S C -0.0252(5) 0.1035(4) 0.2561(2) 0.0238(9) Uani 1 1 d . . .
H1S H -0.0696 0.1753 0.2425 0.029 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01681(13) 0.02044(14) 0.02409(14) -0.00052(11) 0.00149(10) -0.00306(11)
I2 0.01687(13) 0.02186(15) 0.02784(15) -0.00177(12) 0.00001(11) 0.00229(11)
S1 0.0139(4) 0.0199(5) 0.0184(5) -0.0018(4) -0.0040(4) -0.0024(4)
N1 0.0130(16) 0.0123(16) 0.0206(17) -0.0021(13) -0.0001(13) 0.0004(12)
C1 0.0169(19) 0.022(2) 0.0154(18) 0.0038(15) -0.0012(15) -0.0005(16)
C2 0.020(2) 0.020(2) 0.0160(19) -0.0033(15) -0.0007(15) -0.0003(16)
C3 0.0173(18) 0.0130(18) 0.0160(18) -0.0020(14) 0.0016(14) 0.0024(15)
C4 0.0119(16) 0.0090(17) 0.0138(17) -0.0001(12) -0.0027(13) -0.0003(13)
C5 0.0129(17) 0.0057(17) 0.0160(17) 0.0022(13) 0.0017(13) 0.0014(13)
C6 0.0108(17) 0.0141(18) 0.0176(19) -0.0022(15) -0.0024(14) 0.0021(14)
C7 0.0114(16) 0.021(2) 0.0152(16) -0.0014(16) 0.0004(13) -0.0010(16)
C8 0.020(2) 0.011(2) 0.0147(17) -0.0024(14) -0.0030(15) -0.0015(15)
C9 0.019(2) 0.019(2) 0.0161(19) 0.0020(16) 0.0054(15) -0.0020(16)
C10 0.0152(18) 0.0136(18) 0.0214(19) -0.0018(16) 0.0052(15) 0.0015(15)
C11 0.024(2) 0.021(2) 0.044(3) -0.007(2) 0.005(2) 0.0059(19)
C12 0.020(2) 0.018(2) 0.027(2) 0.0099(17) -0.0002(17) 0.0050(16)
C13 0.016(2) 0.024(2) 0.023(2) -0.0023(18) 0.0005(16) -0.0014(17)
C14 0.017(2) 0.019(2) 0.028(2) -0.0040(17) 0.0014(17) -0.0061(16)
C15 0.0151(17) 0.0153(18) 0.0123(15) -0.0014(15) 0.0013(13) 0.0027(16)
C16 0.0161(18) 0.015(2) 0.0150(18) -0.0019(15) -0.0028(14) 0.0000(15)
C17 0.022(2) 0.015(2) 0.0180(19) -0.0050(15) 0.0015(16) -0.0037(16)
C18 0.035(3) 0.0104(18) 0.019(2) -0.0006(15) 0.0038(18) 0.0039(17)
C19 0.029(2) 0.022(2) 0.017(2) 0.0026(18) 0.0033(17) 0.0101(19)
C20 0.0159(19) 0.019(2) 0.019(2) -0.0022(16) 0.0056(15) 0.0010(16)
S2 0.0120(4) 0.0214(5) 0.0153(4) -0.0020(4) -0.0039(3) -0.0002(4)
N2 0.0131(15) 0.0127(16) 0.0156(16) 0.0003(12) -0.0014(12) -0.0028(12)
C21 0.0160(18) 0.021(2) 0.0128(16) 0.0012(17) -0.0033(13) -0.0001(17)
C22 0.0154(19) 0.0156(19) 0.0173(19) -0.0025(15) -0.0044(15) 0.0019(15)
C23 0.0160(18) 0.0124(18) 0.0127(17) -0.0005(14) -0.0038(14) 0.0023(14)
C24 0.0132(16) 0.0090(17) 0.0151(16) -0.0021(14) 0.0012(12) -0.0023(14)
C25 0.0161(19) 0.0156(19) 0.0092(17) 0.0010(14) -0.0026(14) 0.0000(15)
C26 0.0115(17) 0.015(2) 0.0130(17) -0.0025(14) -0.0032(13) 0.0027(14)
C27 0.0143(17) 0.0141(19) 0.0140(16) 0.0030(13) -0.0027(13) -0.0004(14)
C28 0.017(2) 0.023(2) 0.0142(19) -0.0048(16) -0.0022(15) -0.0032(17)
C29 0.0119(17) 0.0178(19) 0.0148(18) 0.0012(15) 0.0001(14) -0.0006(15)
C30 0.0134(18) 0.0101(17) 0.022(2) -0.0033(14) -0.0045(15) 0.0000(14)
C31 0.022(2) 0.018(2) 0.037(3) -0.0068(19) 0.0037(19) 0.0034(17)
C32 0.017(2) 0.018(2) 0.027(2) 0.0061(17) -0.0006(17) 0.0031(16)
C33 0.0155(19) 0.018(2) 0.020(2) -0.0032(16) 0.0012(15) -0.0020(15)
C34 0.0154(19) 0.021(2) 0.029(2) 0.0029(17) -0.0014(17) -0.0049(17)
C35 0.0173(18) 0.012(2) 0.0107(16) -0.0028(13) 0.0015(13) 0.0000(14)
C36 0.0157(19) 0.019(2) 0.0155(18) -0.0021(15) -0.0002(15) -0.0011(16)
C37 0.030(2) 0.0151(19) 0.0114(17) -0.0015(15) -0.0002(16) 0.0014(17)
C38 0.033(2) 0.0114(19) 0.022(2) -0.0005(16) -0.0021(18) 0.0065(17)
C39 0.026(2) 0.019(2) 0.018(2) -0.0002(16) 0.0032(17) 0.0081(18)
C40 0.0145(18) 0.017(2) 0.0146(18) -0.0001(15) 0.0000(14) 0.0042(15)
Cl1S 0.0303(6) 0.0529(8) 0.0400(7) 0.0029(7) 0.0027(5) -0.0152(6)
Cl2S 0.0294(6) 0.0470(8) 0.0288(6) 0.0017(5) 0.0109(5) 0.0063(5)
Cl3S 0.0306(6) 0.0188(5) 0.0241(5) 0.0029(4) 0.0020(4) 0.0020(4)
C1S 0.024(2) 0.023(2) 0.025(2) 0.0027(17) 0.0073(17) 0.0049(17)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C6 1.752(4) . ?
S1 C1 1.805(4) . ?
N1 C6 1.299(5) . ?
N1 C14 1.472(5) . ?
N1 C9 1.481(5) . ?
C1 C2 1.530(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.543(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.537(5) . ?
C3 C10 1.558(6) . ?
C3 H3 1.0000 . ?
C4 C5 1.576(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C15 1.531(6) . ?
C5 C6 1.542(6) . ?
C5 C7 1.542(5) . ?
C7 C8 1.510(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.510(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C13 1.529(6) . ?
C10 C11 1.536(6) . ?
C10 C12 1.539(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.396(6) . ?
C15 C16 1.408(6) . ?
C16 C17 1.390(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.402(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(7) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
S2 C26 1.740(4) . ?
S2 C21 1.803(4) . ?
N2 C26 1.301(5) . ?
N2 C29 1.477(5) . ?
N2 C34 1.481(5) . ?
C21 C22 1.527(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.547(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.540(5) . ?
C23 C30 1.555(5) . ?
C23 H23 1.0000 . ?
C24 C25 1.577(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C35 1.532(6) . ?
C25 C26 1.543(6) . ?
C25 C27 1.561(5) . ?
C27 C28 1.524(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.515(6) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C32 1.522(6) . ?
C30 C33 1.542(6) . ?
C30 C31 1.547(6) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C40 1.396(6) . ?
C35 C36 1.398(6) . ?
C36 C37 1.383(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.371(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.387(7) . ?
C38 H38 0.9500 . ?
C39 C40 1.394(6) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
Cl1S C1S 1.762(5) . ?
Cl2S C1S 1.751(5) . ?
Cl3S C1S 1.749(5) . ?
C1S H1S 1.0000 . ?

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
C6 S1 C1 104.6(2) . . ?
C6 N1 C14 122.5(4) . . ?
C6 N1 C9 126.1(4) . . ?
C14 N1 C9 111.2(3) . . ?
C2 C1 S1 113.0(3) . . ?
C2 C1 H1A 109.0 . . ?
S1 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
S1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 C3 112.3(3) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 108.7(3) . . ?
C4 C3 C10 112.3(3) . . ?
C2 C3 C10 112.4(3) . . ?
C4 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
C10 C3 H3 107.7 . . ?
C3 C4 C5 117.2(3) . . ?
C3 C4 H4A 108.0 . . ?
C5 C4 H4A 108.0 . . ?
C3 C4 H4B 108.0 . . ?
C5 C4 H4B 108.0 . . ?
H4A C4 H4B 107.2 . . ?
C15 C5 C6 110.0(3) . . ?
C15 C5 C7 109.6(3) . . ?
C6 C5 C7 107.8(3) . . ?
C15 C5 C4 109.2(3) . . ?
C6 C5 C4 114.2(3) . . ?
C7 C5 C4 105.8(3) . . ?
N1 C6 C5 121.7(4) . . ?
N1 C6 S1 114.1(3) . . ?
C5 C6 S1 124.2(3) . . ?
C8 C7 C5 110.6(3) . . ?
C8 C7 H7A 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C7 109.0(3) . . ?
C9 C8 H8A 109.9 . . ?
C7 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N1 C9 C8 112.4(3) . . ?
N1 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C13 C10 C11 109.8(4) . . ?
C13 C10 C12 108.7(4) . . ?
C11 C10 C12 107.8(4) . . ?
C13 C10 C3 112.4(4) . . ?
C11 C10 C3 109.4(3) . . ?
C12 C10 C3 108.6(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.0(4) . . ?
C20 C15 C5 124.5(4) . . ?
C16 C15 C5 117.5(3) . . ?
C17 C16 C15 121.1(4) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.6(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 120.3(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C15 121.0(4) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C26 S2 C21 105.00(19) . . ?
C26 N2 C29 126.9(3) . . ?
C26 N2 C34 121.7(4) . . ?
C29 N2 C34 111.4(3) . . ?
C22 C21 S2 112.5(3) . . ?
C22 C21 H21A 109.1 . . ?
S2 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
S2 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 C23 112.7(3) . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C22 108.0(3) . . ?
C24 C23 C30 113.0(3) . . ?
C22 C23 C30 114.2(3) . . ?
C24 C23 H23 107.1 . . ?
C22 C23 H23 107.1 . . ?
C30 C23 H23 107.1 . . ?
C23 C24 C25 116.2(3) . . ?
C23 C24 H24A 108.2 . . ?
C25 C24 H24A 108.2 . . ?
C23 C24 H24B 108.2 . . ?
C25 C24 H24B 108.2 . . ?
H24A C24 H24B 107.4 . . ?
C35 C25 C26 111.0(3) . . ?
C35 C25 C27 109.1(3) . . ?
C26 C25 C27 107.7(3) . . ?
C35 C25 C24 110.7(3) . . ?
C26 C25 C24 113.2(3) . . ?
C27 C25 C24 104.9(3) . . ?
N2 C26 C25 120.9(3) . . ?
N2 C26 S2 115.0(3) . . ?
C25 C26 S2 123.9(3) . . ?
C28 C27 C25 110.4(3) . . ?
C28 C27 H27A 109.6 . . ?
C25 C27 H27A 109.6 . . ?
C28 C27 H27B 109.6 . . ?
C25 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
C29 C28 C27 108.2(4) . . ?
C29 C28 H28A 110.1 . . ?
C27 C28 H28A 110.1 . . ?
C29 C28 H28B 110.1 . . ?
C27 C28 H28B 110.1 . . ?
H28A C28 H28B 108.4 . . ?
N2 C29 C28 113.2(3) . . ?
N2 C29 H29A 108.9 . . ?
C28 C29 H29A 108.9 . . ?
N2 C29 H29B 108.9 . . ?
C28 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
C32 C30 C33 108.8(3) . . ?
C32 C30 C31 108.5(4) . . ?
C33 C30 C31 109.4(4) . . ?
C32 C30 C23 109.5(3) . . ?
C33 C30 C23 111.6(3) . . ?
C31 C30 C23 109.1(3) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N2 C34 H34A 109.5 . . ?
N2 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N2 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C40 C35 C36 118.8(4) . . ?
C40 C35 C25 121.9(4) . . ?
C36 C35 C25 119.2(4) . . ?
C37 C36 C35 120.0(4) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C38 C37 C36 121.8(4) . . ?
C38 C37 H37 119.1 . . ?
C36 C37 H37 119.1 . . ?
C37 C38 C39 118.4(4) . . ?
C37 C38 H38 120.8 . . ?
C39 C38 H38 120.8 . . ?
C38 C39 C40 121.2(4) . . ?
C38 C39 H39 119.4 . . ?
C40 C39 H39 119.4 . . ?
C39 C40 C35 119.7(4) . . ?
C39 C40 H40 120.2 . . ?
C35 C40 H40 120.2 . . ?
Cl3S C1S Cl2S 111.0(3) . . ?
Cl3S C1S Cl1S 111.5(2) . . ?
Cl2S C1S Cl1S 110.3(3) . . ?
Cl3S C1S H1S 108.0 . . ?
Cl2S C1S H1S 108.0 . . ?
Cl1S C1S H1S 108.0 . . ?

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
C6 S1 C1 C2 71.4(3) . . . . ?
S1 C1 C2 C3 -57.5(4) . . . . ?
C1 C2 C3 C4 -40.6(5) . . . . ?
C1 C2 C3 C10 -165.5(4) . . . . ?
C2 C3 C4 C5 92.8(4) . . . . ?
C10 C3 C4 C5 -142.2(3) . . . . ?
C3 C4 C5 C15 -142.9(3) . . . . ?
C3 C4 C5 C6 -19.2(5) . . . . ?
C3 C4 C5 C7 99.2(4) . . . . ?
C14 N1 C6 C5 -177.5(4) . . . . ?
C9 N1 C6 C5 6.9(6) . . . . ?
C14 N1 C6 S1 4.2(5) . . . . ?
C9 N1 C6 S1 -171.4(3) . . . . ?
C15 C5 C6 N1 -102.7(4) . . . . ?
C7 C5 C6 N1 16.8(5) . . . . ?
C4 C5 C6 N1 134.0(4) . . . . ?
C15 C5 C6 S1 75.4(4) . . . . ?
C7 C5 C6 S1 -165.1(3) . . . . ?
C4 C5 C6 S1 -47.9(5) . . . . ?
C1 S1 C6 N1 -168.5(3) . . . . ?
C1 S1 C6 C5 13.2(4) . . . . ?
C15 C5 C7 C8 67.3(4) . . . . ?
C6 C5 C7 C8 -52.5(4) . . . . ?
C4 C5 C7 C8 -175.0(3) . . . . ?
C5 C7 C8 C9 66.0(5) . . . . ?
C6 N1 C9 C8 5.2(6) . . . . ?
C14 N1 C9 C8 -170.8(4) . . . . ?
C7 C8 C9 N1 -40.5(5) . . . . ?
C4 C3 C10 C13 -53.0(4) . . . . ?
C2 C3 C10 C13 69.9(5) . . . . ?
C4 C3 C10 C11 -175.3(4) . . . . ?
C2 C3 C10 C11 -52.3(5) . . . . ?
C4 C3 C10 C12 67.3(4) . . . . ?
C2 C3 C10 C12 -169.7(4) . . . . ?
C6 C5 C15 C20 1.7(5) . . . . ?
C7 C5 C15 C20 -116.6(4) . . . . ?
C4 C5 C15 C20 127.9(4) . . . . ?
C6 C5 C15 C16 -179.0(3) . . . . ?
C7 C5 C15 C16 62.7(4) . . . . ?
C4 C5 C15 C16 -52.8(4) . . . . ?
C20 C15 C16 C17 0.4(6) . . . . ?
C5 C15 C16 C17 -178.9(4) . . . . ?
C15 C16 C17 C18 -1.3(6) . . . . ?
C16 C17 C18 C19 0.5(6) . . . . ?
C17 C18 C19 C20 1.2(7) . . . . ?
C18 C19 C20 C15 -2.2(7) . . . . ?
C16 C15 C20 C19 1.3(6) . . . . ?
C5 C15 C20 C19 -179.4(4) . . . . ?
C26 S2 C21 C22 -69.6(3) . . . . ?
S2 C21 C22 C23 56.3(4) . . . . ?
C21 C22 C23 C24 41.8(4) . . . . ?
C21 C22 C23 C30 168.3(3) . . . . ?
C22 C23 C24 C25 -93.7(4) . . . . ?
C30 C23 C24 C25 139.1(3) . . . . ?
C23 C24 C25 C35 143.6(3) . . . . ?
C23 C24 C25 C26 18.3(5) . . . . ?
C23 C24 C25 C27 -98.9(4) . . . . ?
C29 N2 C26 C25 -6.5(6) . . . . ?
C34 N2 C26 C25 177.2(4) . . . . ?
C29 N2 C26 S2 169.0(3) . . . . ?
C34 N2 C26 S2 -7.2(5) . . . . ?
C35 C25 C26 N2 101.0(4) . . . . ?
C27 C25 C26 N2 -18.4(5) . . . . ?
C24 C25 C26 N2 -133.9(4) . . . . ?
C35 C25 C26 S2 -74.2(4) . . . . ?
C27 C25 C26 S2 166.5(3) . . . . ?
C24 C25 C26 S2 51.0(5) . . . . ?
C21 S2 C26 N2 168.4(3) . . . . ?
C21 S2 C26 C25 -16.2(4) . . . . ?
C35 C25 C27 C28 -66.6(4) . . . . ?
C26 C25 C27 C28 53.9(5) . . . . ?
C24 C25 C27 C28 174.8(3) . . . . ?
C25 C27 C28 C29 -65.6(5) . . . . ?
C26 N2 C29 C28 -4.3(6) . . . . ?
C34 N2 C29 C28 172.3(4) . . . . ?
C27 C28 C29 N2 39.4(5) . . . . ?
C24 C23 C30 C32 -65.5(4) . . . . ?
C22 C23 C30 C32 170.6(3) . . . . ?
C24 C23 C30 C33 55.0(4) . . . . ?
C22 C23 C30 C33 -69.0(4) . . . . ?
C24 C23 C30 C31 175.9(3) . . . . ?
C22 C23 C30 C31 52.0(5) . . . . ?
C26 C25 C35 C40 -7.8(5) . . . . ?
C27 C25 C35 C40 110.7(4) . . . . ?
C24 C25 C35 C40 -134.4(4) . . . . ?
C26 C25 C35 C36 175.1(3) . . . . ?
C27 C25 C35 C36 -66.4(5) . . . . ?
C24 C25 C35 C36 48.5(5) . . . . ?
C40 C35 C36 C37 -0.8(6) . . . . ?
C25 C35 C36 C37 176.4(4) . . . . ?
C35 C36 C37 C38 1.9(6) . . . . ?
C36 C37 C38 C39 -1.4(7) . . . . ?
C37 C38 C39 C40 -0.2(7) . . . . ?
C38 C39 C40 C35 1.3(7) . . . . ?
C36 C35 C40 C39 -0.7(6) . . . . ?
C25 C35 C40 C39 -177.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         2.661
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.142