#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012852.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012852
loop_
_publ_author_name
'Linden, Anthony'
'Majchrzak, Agnieszka'
'Cavegn, Jovita'
'Mloston, Grzegorz'
'Heimgartner, Heinz'
_publ_section_title
;
 Four
 bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutan-1-yl)oligosulfanes
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o480
_journal_page_last               o484
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C16 H24 Cl2 O2 S4'
_chemical_formula_sum            'C16 H24 Cl2 O2 S4'
_chemical_formula_weight         447.51
_chemical_melting_point          .405E-305
_chemical_name_systematic
;
1,4-bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutan-1-yl)tetrasulfane
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                71.8478(5)
_cell_angle_beta                 89.8055(5)
_cell_angle_gamma                73.5431(5)
_cell_formula_units_Z            4
_cell_length_a                   11.13720(10)
_cell_length_b                   13.08430(10)
_cell_length_c                   16.3379(2)
_cell_measurement_reflns_used    39875
_cell_measurement_temperature    253.0(10)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     2160.20(4)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2002)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      253.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '\f and \w scans with \k offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR591 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.038
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_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            61153
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.56
_refine_ls_extinction_coef       0.0049(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         12596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.065
_refine_ls_R_factor_gt           0.041
_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/[\s^2^(Fo^2^)+(0.0529P)^2^+0.5211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.102
_refine_ls_wR_factor_ref         0.114
_reflns_number_gt                9118
_reflns_number_total             12599
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm1503.cif
_[local]_cod_data_source_block   VII
_cod_database_code               2012852
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cl1 0.60123(4) 0.27674(4) 0.08168(4) 0.05255(13) Uani d . 1 Cl
Cl2 0.89837(4) -0.26835(4) 0.22743(3) 0.05085(12) Uani d . 1 Cl
S1 0.56483(4) 0.10689(4) 0.01143(3) 0.04517(12) Uani d . 1 S
S2 0.66408(5) -0.00384(4) 0.12373(4) 0.05424(14) Uani d . 1 S
S3 0.84544(5) 0.00729(4) 0.11382(4) 0.05064(13) Uani d . 1 S
S4 0.93563(4) -0.11413(4) 0.06302(3) 0.04337(12) Uani d . 1 S
O1 0.17854(16) 0.3565(2) 0.01191(17) 0.1224(9) Uani d . 1 O
O2 1.31772(15) -0.37814(19) 0.19871(14) 0.0945(7) Uani d . 1 O
C1 0.48584(15) 0.23044(13) 0.04065(11) 0.0343(3) Uani d . 1 C
C2 0.39258(17) 0.32410(15) -0.03731(12) 0.0418(4) Uani d . 1 C
C3 0.28888(18) 0.31110(19) 0.02201(15) 0.0580(5) Uani d . 1 C
C4 0.37223(18) 0.22151(17) 0.09875(13) 0.0474(4) Uani d . 1 C
C5 0.4078(2) 0.44162(17) -0.06262(18) 0.0703(7) Uani d . 1 C
H51 0.3373 0.4942 -0.1017 0.105 Uiso calc R 1 H
H52 0.4839 0.4419 -0.0904 0.105 Uiso calc R 1 H
H53 0.4118 0.4629 -0.0117 0.105 Uiso calc R 1 H
C6 0.3788(3) 0.2939(2) -0.11876(15) 0.0726(7) Uani d . 1 C
H61 0.3696 0.2196 -0.1032 0.109 Uiso calc R 1 H
H62 0.4521 0.2959 -0.1495 0.109 Uiso calc R 1 H
H63 0.3058 0.3471 -0.1550 0.109 Uiso calc R 1 H
C7 0.3726(3) 0.2580(3) 0.17796(18) 0.0877(9) Uani d . 1 C
H71 0.3933 0.3276 0.1630 0.132 Uiso calc R 1 H
H72 0.4340 0.2012 0.2221 0.132 Uiso calc R 1 H
H73 0.2909 0.2684 0.1990 0.132 Uiso calc R 1 H
C8 0.3372(3) 0.1111(2) 0.1199(2) 0.0826(8) Uani d . 1 C
H81 0.2537 0.1226 0.1380 0.124 Uiso calc R 1 H
H82 0.3956 0.0536 0.1656 0.124 Uiso calc R 1 H
H83 0.3406 0.0882 0.0693 0.124 Uiso calc R 1 H
C9 1.01452(15) -0.23266(13) 0.15743(10) 0.0348(3) Uani d . 1 C
C10 1.13192(17) -0.22354(16) 0.20647(11) 0.0425(4) Uani d . 1 C
C11 1.20871(18) -0.32457(18) 0.18258(13) 0.0520(5) Uani d . 1 C
C12 1.10139(17) -0.33522(15) 0.13192(12) 0.0424(4) Uani d . 1 C
C13 1.1754(2) -0.1200(2) 0.16386(17) 0.0670(6) Uani d . 1 C
H131 1.2586 -0.1323 0.1883 0.101 Uiso calc R 1 H
H132 1.1188 -0.0554 0.1738 0.101 Uiso calc R 1 H
H133 1.1762 -0.1074 0.1028 0.101 Uiso calc R 1 H
C14 1.1296(2) -0.2448(2) 0.30343(13) 0.0623(6) Uani d . 1 C
H141 1.1035 -0.3106 0.3295 0.094 Uiso calc R 1 H
H142 1.0717 -0.1810 0.3136 0.094 Uiso calc R 1 H
H143 1.2122 -0.2560 0.3283 0.094 Uiso calc R 1 H
C15 1.1186(2) -0.3129(2) 0.03568(14) 0.0623(6) Uani d . 1 C
H151 1.1399 -0.2438 0.0127 0.093 Uiso calc R 1 H
H152 1.0419 -0.3068 0.0055 0.093 Uiso calc R 1 H
H153 1.1850 -0.3739 0.0284 0.093 Uiso calc R 1 H
C16 1.0748(3) -0.44772(17) 0.16906(19) 0.0729(7) Uani d . 1 C
H161 1.1406 -0.5056 0.1574 0.109 Uiso calc R 1 H
H162 0.9958 -0.4435 0.1428 0.109 Uiso calc R 1 H
H163 1.0714 -0.4651 0.2304 0.109 Uiso calc R 1 H
Cl21 0.71636(4) 0.26896(4) 0.27609(3) 0.05166(13) Uani d . 1 Cl
Cl22 0.78294(4) -0.27841(4) 0.41765(3) 0.05102(12) Uani d . 1 Cl
S21 0.86092(4) 0.10730(4) 0.43601(3) 0.04429(12) Uani d . 1 S
S22 0.84084(5) -0.01087(4) 0.38475(4) 0.05559(14) Uani d . 1 S
S23 0.65176(5) 0.00070(4) 0.38499(4) 0.05233(13) Uani d . 1 S
S24 0.63673(4) -0.11695(4) 0.49701(3) 0.04265(11) Uani d . 1 S
O21 1.10527(14) 0.32566(15) 0.33197(12) 0.0692(4) Uani d . 1 O
O22 0.41045(16) -0.35990(16) 0.50155(14) 0.0829(6) Uani d . 1 O
C21 0.86012(15) 0.22684(13) 0.34193(10) 0.0335(3) Uani d . 1 C
C22 0.88989(16) 0.32241(14) 0.37163(11) 0.0388(4) Uani d . 1 C
C23 1.01325(17) 0.29567(15) 0.33082(12) 0.0431(4) Uani d . 1 C
C24 0.98270(17) 0.21408(16) 0.29156(12) 0.0426(4) Uani d . 1 C
C25 0.8050(2) 0.44140(16) 0.32573(17) 0.0616(6) Uani d . 1 C
H251 0.8398 0.4948 0.3381 0.092 Uiso calc R 1 H
H252 0.7228 0.4495 0.3457 0.092 Uiso calc R 1 H
H253 0.7991 0.4548 0.2645 0.092 Uiso calc R 1 H
C26 0.9064(2) 0.30321(19) 0.46888(13) 0.0551(5) Uani d . 1 C
H261 0.9651 0.2304 0.4970 0.083 Uiso calc R 1 H
H262 0.8268 0.3068 0.4924 0.083 Uiso calc R 1 H
H263 0.9377 0.3604 0.4781 0.083 Uiso calc R 1 H
C27 0.9598(3) 0.2629(3) 0.19300(14) 0.0734(7) Uani d . 1 C
H271 0.8985 0.3359 0.1769 0.110 Uiso calc R 1 H
H272 0.9293 0.2139 0.1712 0.110 Uiso calc R 1 H
H273 1.0371 0.2698 0.1691 0.110 Uiso calc R 1 H
C28 1.0834(2) 0.09960(19) 0.31916(19) 0.0715(7) Uani d . 1 C
H281 1.1611 0.1084 0.2969 0.107 Uiso calc R 1 H
H282 1.0571 0.0489 0.2968 0.107 Uiso calc R 1 H
H283 1.0954 0.0696 0.3812 0.107 Uiso calc R 1 H
C29 0.63905(15) -0.23808(13) 0.46431(11) 0.0340(3) Uani d . 1 C
C30 0.51717(17) -0.22879(16) 0.40883(12) 0.0439(4) Uani d . 1 C
C31 0.49517(17) -0.31893(16) 0.48724(14) 0.0470(4) Uani d . 1 C
C32 0.61360(16) -0.33608(14) 0.54180(11) 0.0377(4) Uani d . 1 C
C33 0.4107(2) -0.11863(19) 0.38679(18) 0.0671(6) Uani d . 1 C
H331 0.3349 -0.1297 0.3683 0.101 Uiso calc R 1 H
H332 0.4323 -0.0618 0.3412 0.101 Uiso calc R 1 H
H333 0.3978 -0.0951 0.4371 0.101 Uiso calc R 1 H
C34 0.5400(3) -0.2676(3) 0.32983(17) 0.0788(8) Uani d . 1 C
H341 0.6042 -0.3389 0.3455 0.118 Uiso calc R 1 H
H342 0.5665 -0.2130 0.2853 0.118 Uiso calc R 1 H
H343 0.4636 -0.2753 0.3090 0.118 Uiso calc R 1 H
C35 0.5875(2) -0.31263(19) 0.62719(13) 0.0536(5) Uani d . 1 C
H351 0.5214 -0.2432 0.6167 0.080 Uiso calc R 1 H
H352 0.6623 -0.3069 0.6521 0.080 Uiso calc R 1 H
H353 0.5625 -0.3731 0.6664 0.080 Uiso calc R 1 H
C36 0.7068(2) -0.45262(16) 0.55966(16) 0.0575(5) Uani d . 1 C
H361 0.6748 -0.5076 0.5996 0.086 Uiso calc R 1 H
H362 0.7858 -0.4543 0.5841 0.086 Uiso calc R 1 H
H363 0.7185 -0.4695 0.5065 0.086 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0469(3) 0.0473(2) 0.0673(3) -0.0135(2) -0.0153(2) -0.0240(2)
Cl2 0.0437(2) 0.0562(3) 0.0471(2) -0.0174(2) 0.0174(2) -0.0069(2)
S1 0.0414(2) 0.0395(2) 0.0580(3) -0.00590(18) 0.0044(2) -0.0260(2)
S2 0.0424(3) 0.0353(2) 0.0712(3) -0.00456(19) 0.0114(2) -0.0045(2)
S3 0.0418(2) 0.0357(2) 0.0686(3) -0.00658(19) 0.0008(2) -0.0133(2)
S4 0.0400(2) 0.0396(2) 0.0368(2) -0.00300(18) 0.00100(18) -0.00131(17)
O1 0.0365(9) 0.157(2) 0.1247(19) 0.0091(11) 0.0002(10) -0.0116(17)
O2 0.0406(8) 0.1137(16) 0.1145(16) 0.0145(9) -0.0085(9) -0.0503(13)
C1 0.0340(8) 0.0317(8) 0.0396(8) -0.0075(6) -0.0006(7) -0.0169(7)
C2 0.0409(9) 0.0379(9) 0.0442(9) -0.0079(7) -0.0094(7) -0.0131(7)
C3 0.0347(10) 0.0636(13) 0.0720(14) -0.0055(9) -0.0024(9) -0.0248(11)
C4 0.0413(9) 0.0500(10) 0.0512(11) -0.0082(8) 0.0108(8) -0.0220(9)
C5 0.0737(15) 0.0382(11) 0.0850(17) -0.0130(10) -0.0269(13) -0.0036(11)
C6 0.0919(18) 0.0664(14) 0.0528(13) -0.0107(13) -0.0253(12) -0.0212(11)
C7 0.0714(16) 0.135(3) 0.0709(16) -0.0168(17) 0.0218(13) -0.0654(18)
C8 0.0723(16) 0.0681(16) 0.114(2) -0.0333(13) 0.0504(16) -0.0277(15)
C9 0.0327(8) 0.0341(8) 0.0308(7) -0.0082(6) 0.0062(6) -0.0028(6)
C10 0.0376(9) 0.0464(10) 0.0387(9) -0.0125(7) -0.0004(7) -0.0069(7)
C11 0.0375(9) 0.0558(11) 0.0490(11) -0.0018(8) 0.0033(8) -0.0090(9)
C12 0.0417(9) 0.0359(9) 0.0420(9) -0.0055(7) 0.0079(7) -0.0077(7)
C13 0.0575(13) 0.0668(14) 0.0740(15) -0.0328(11) -0.0081(11) -0.0057(12)
C14 0.0646(14) 0.0743(15) 0.0437(11) -0.0168(11) -0.0045(10) -0.0165(10)
C15 0.0666(14) 0.0651(13) 0.0503(11) -0.0059(11) 0.0164(10) -0.0242(10)
C16 0.0795(16) 0.0354(10) 0.0953(19) -0.0125(10) 0.0229(14) -0.0137(11)
Cl21 0.0417(2) 0.0611(3) 0.0467(2) -0.0195(2) -0.01057(19) -0.0061(2)
Cl22 0.0413(2) 0.0602(3) 0.0593(3) -0.0160(2) 0.0225(2) -0.0293(2)
S21 0.0460(2) 0.0407(2) 0.0400(2) -0.01731(19) 0.00370(19) -0.00060(18)
S22 0.0479(3) 0.0388(2) 0.0826(4) -0.0179(2) 0.0207(3) -0.0189(2)
S23 0.0466(3) 0.0393(2) 0.0653(3) -0.0165(2) 0.0033(2) -0.0055(2)
S24 0.0485(3) 0.0383(2) 0.0513(3) -0.02035(19) 0.0137(2) -0.02189(19)
O21 0.0495(8) 0.0782(11) 0.0864(11) -0.0385(8) 0.0095(8) -0.0178(9)
O22 0.0601(10) 0.0906(13) 0.1084(14) -0.0508(10) 0.0003(10) -0.0210(11)
C21 0.0308(7) 0.0354(8) 0.0312(7) -0.0110(6) -0.0009(6) -0.0054(6)
C22 0.0366(8) 0.0362(8) 0.0429(9) -0.0128(7) 0.0006(7) -0.0101(7)
C23 0.0371(9) 0.0423(9) 0.0436(9) -0.0160(7) -0.0002(7) -0.0013(7)
C24 0.0381(9) 0.0477(10) 0.0413(9) -0.0154(8) 0.0110(7) -0.0113(8)
C25 0.0617(13) 0.0354(10) 0.0799(15) -0.0083(9) -0.0055(11) -0.0133(10)
C26 0.0573(12) 0.0679(13) 0.0503(11) -0.0235(10) 0.0036(9) -0.0290(10)
C27 0.0782(16) 0.109(2) 0.0406(11) -0.0441(15) 0.0206(11) -0.0205(12)
C28 0.0534(13) 0.0551(13) 0.1012(19) -0.0112(10) 0.0349(13) -0.0233(13)
C29 0.0322(8) 0.0356(8) 0.0393(8) -0.0114(6) 0.0100(6) -0.0183(7)
C30 0.0386(9) 0.0501(10) 0.0470(10) -0.0117(8) 0.0001(8) -0.0228(8)
C31 0.0389(9) 0.0474(10) 0.0641(12) -0.0190(8) 0.0055(9) -0.0255(9)
C32 0.0368(8) 0.0367(8) 0.0444(9) -0.0162(7) 0.0087(7) -0.0150(7)
C33 0.0448(11) 0.0580(13) 0.0910(17) -0.0071(10) -0.0153(11) -0.0211(12)
C34 0.0703(16) 0.121(2) 0.0684(15) -0.0312(15) 0.0041(12) -0.0609(16)
C35 0.0619(12) 0.0618(12) 0.0455(10) -0.0295(10) 0.0202(9) -0.0193(9)
C36 0.0548(12) 0.0375(10) 0.0741(14) -0.0110(9) 0.0052(11) -0.0122(9)
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 for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
Cl Cl 0.1484 0.1585
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O 0.0106 0.0060
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
S S 0.1246 0.1234
; International Tables for Crystallography (1992).
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_publ_flag
C1 S1 S2 103.59(6) yes
S1 S2 S3 105.29(3) yes
S4 S3 S2 105.17(3) yes
C9 S4 S3 103.61(6) yes
C2 C1 C4 90.73(13) yes
C2 C1 Cl1 114.49(11) ?
C4 C1 Cl1 114.32(12) ?
C2 C1 S1 111.37(11) ?
C4 C1 S1 116.46(12) ?
Cl1 C1 S1 108.69(9) ?
C3 C2 C6 114.36(18) ?
C3 C2 C5 112.44(18) ?
C6 C2 C5 109.08(19) ?
C1 C2 C3 86.31(14) yes
C6 C2 C1 116.78(15) ?
C5 C2 C1 116.41(14) ?
O1 C3 C4 131.5(2) ?
O1 C3 C2 132.0(2) ?
C2 C3 C4 96.49(14) yes
C3 C4 C7 113.43(19) ?
C3 C4 C8 110.7(2) ?
C7 C4 C8 111.0(2) ?
C1 C4 C3 86.48(14) yes
C7 C4 C1 116.82(18) ?
C8 C4 C1 116.18(16) ?
C2 C5 H51 109.5 ?
C2 C5 H52 109.5 ?
H51 C5 H52 109.5 ?
C2 C5 H53 109.5 ?
H51 C5 H53 109.5 ?
H52 C5 H53 109.5 ?
C2 C6 H61 109.5 ?
C2 C6 H62 109.5 ?
H61 C6 H62 109.5 ?
C2 C6 H63 109.5 ?
H61 C6 H63 109.5 ?
H62 C6 H63 109.5 ?
C4 C7 H71 109.5 ?
C4 C7 H72 109.5 ?
H71 C7 H72 109.5 ?
C4 C7 H73 109.5 ?
H71 C7 H73 109.5 ?
H72 C7 H73 109.5 ?
C4 C8 H81 109.5 ?
C4 C8 H82 109.5 ?
H81 C8 H82 109.5 ?
C4 C8 H83 109.5 ?
H81 C8 H83 109.5 ?
H82 C8 H83 109.5 ?
C10 C9 C12 90.97(13) yes
C12 C9 Cl2 113.88(12) ?
C10 C9 Cl2 113.23(11) ?
C12 C9 S4 112.18(11) ?
C10 C9 S4 117.55(12) ?
Cl2 C9 S4 108.35(8) ?
C11 C10 C14 114.11(16) ?
C11 C10 C13 111.16(18) ?
C14 C10 C13 110.31(18) ?
C9 C10 C11 86.27(14) yes
C14 C10 C9 116.96(16) ?
C13 C10 C9 116.06(15) ?
O2 C11 C12 131.9(2) ?
O2 C11 C10 131.7(2) ?
C10 C11 C12 96.36(14) yes
C11 C12 C16 113.43(18) ?
C11 C12 C15 113.42(17) ?
C16 C12 C15 109.28(19) ?
C9 C12 C11 86.32(14) yes
C16 C12 C9 116.72(16) ?
C15 C12 C9 116.15(15) ?
C10 C13 H131 109.5 ?
C10 C13 H132 109.5 ?
H131 C13 H132 109.5 ?
C10 C13 H133 109.5 ?
H131 C13 H133 109.5 ?
H132 C13 H133 109.5 ?
C10 C14 H141 109.5 ?
C10 C14 H142 109.5 ?
H141 C14 H142 109.5 ?
C10 C14 H143 109.5 ?
H141 C14 H143 109.5 ?
H142 C14 H143 109.5 ?
C12 C15 H151 109.5 ?
C12 C15 H152 109.5 ?
H151 C15 H152 109.5 ?
C12 C15 H153 109.5 ?
H151 C15 H153 109.5 ?
H152 C15 H153 109.5 ?
C12 C16 H161 109.5 ?
C12 C16 H162 109.5 ?
H161 C16 H162 109.5 ?
C12 C16 H163 109.5 ?
H161 C16 H163 109.5 ?
H162 C16 H163 109.5 ?
C21 S21 S22 103.93(6) yes
S21 S22 S23 105.30(3) yes
S24 S23 S22 105.29(3) yes
C29 S24 S23 103.69(6) yes
C22 C21 C24 90.73(13) yes
C24 C21 Cl21 114.91(11) ?
C22 C21 Cl21 115.54(11) ?
C24 C21 S21 116.10(11) ?
C22 C21 S21 109.99(11) ?
Cl21 C21 S21 108.74(9) ?
C23 C22 C25 112.44(16) ?
C23 C22 C26 113.98(15) ?
C25 C22 C26 109.62(17) ?
C21 C22 C23 86.14(13) yes
C25 C22 C21 114.97(15) ?
C26 C22 C21 117.99(15) ?
O21 C23 C24 131.90(19) ?
O21 C23 C22 132.05(19) ?
C22 C23 C24 96.00(13) yes
C23 C24 C27 111.86(17) ?
C23 C24 C28 112.30(17) ?
C27 C24 C28 110.66(19) ?
C21 C24 C23 86.43(13) yes
C27 C24 C21 115.46(16) ?
C28 C24 C21 117.98(16) ?
C22 C25 H251 109.5 ?
C22 C25 H252 109.5 ?
H251 C25 H252 109.5 ?
C22 C25 H253 109.5 ?
H251 C25 H253 109.5 ?
H252 C25 H253 109.5 ?
C22 C26 H261 109.5 ?
C22 C26 H262 109.5 ?
H261 C26 H262 109.5 ?
C22 C26 H263 109.5 ?
H261 C26 H263 109.5 ?
H262 C26 H263 109.5 ?
C24 C27 H271 109.5 ?
C24 C27 H272 109.5 ?
H271 C27 H272 109.5 ?
C24 C27 H273 109.5 ?
H271 C27 H273 109.5 ?
H272 C27 H273 109.5 ?
C24 C28 H281 109.5 ?
C24 C28 H282 109.5 ?
H281 C28 H282 109.5 ?
C24 C28 H283 109.5 ?
H281 C28 H283 109.5 ?
H282 C28 H283 109.5 ?
C30 C29 C32 90.69(13) yes
C32 C29 Cl22 114.56(11) ?
C30 C29 Cl22 114.38(11) ?
C32 C29 S24 111.46(11) ?
C30 C29 S24 116.68(11) ?
Cl22 C29 S24 108.37(9) ?
C31 C30 C34 112.67(19) ?
C31 C30 C33 112.08(18) ?
C34 C30 C33 110.45(19) ?
C29 C30 C31 86.44(13) yes
C34 C30 C29 116.14(16) ?
C33 C30 C29 117.03(15) ?
O22 C31 C32 132.2(2) ?
O22 C31 C30 131.61(19) ?
C30 C31 C32 96.12(14) yes
C31 C32 C36 112.84(15) ?
C31 C32 C35 113.31(16) ?
C36 C32 C35 109.50(17) ?
C29 C32 C31 86.63(13) yes
C36 C32 C29 116.09(15) ?
C35 C32 C29 116.88(14) ?
C30 C33 H331 109.5 ?
C30 C33 H332 109.5 ?
H331 C33 H332 109.5 ?
C30 C33 H333 109.5 ?
H331 C33 H333 109.5 ?
H332 C33 H333 109.5 ?
C30 C34 H341 109.5 ?
C30 C34 H342 109.5 ?
H341 C34 H342 109.5 ?
C30 C34 H343 109.5 ?
H341 C34 H343 109.5 ?
H342 C34 H343 109.5 ?
C32 C35 H351 109.5 ?
C32 C35 H352 109.5 ?
H351 C35 H352 109.5 ?
C32 C35 H353 109.5 ?
H351 C35 H353 109.5 ?
H352 C35 H353 109.5 ?
C32 C36 H361 109.5 ?
C32 C36 H362 109.5 ?
H361 C36 H362 109.5 ?
C32 C36 H363 109.5 ?
H361 C36 H363 109.5 ?
H362 C36 H363 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.7799(16) yes
Cl2 C9 1.7885(16) yes
S1 C1 1.8131(16) yes
S1 S2 2.0341(7) yes
S2 S3 2.0680(7) yes
S3 S4 2.0332(7) yes
S4 C9 1.8174(16) yes
O1 C3 1.190(3) ?
O2 C11 1.200(2) ?
C1 C2 1.587(2) yes
C1 C4 1.588(3) yes
C2 C3 1.518(3) ?
C2 C6 1.521(3) ?
C2 C5 1.522(3) ?
C3 C4 1.511(3) ?
C4 C7 1.513(3) ?
C4 C8 1.538(3) ?
C5 H51 0.9600 ?
C5 H52 0.9600 ?
C5 H53 0.9600 ?
C6 H61 0.9600 ?
C6 H62 0.9600 ?
C6 H63 0.9600 ?
C7 H71 0.9600 ?
C7 H72 0.9600 ?
C7 H73 0.9600 ?
C8 H81 0.9600 ?
C8 H82 0.9600 ?
C8 H83 0.9600 ?
C9 C10 1.588(2) yes
C9 C12 1.588(2) yes
C10 C11 1.520(3) ?
C10 C14 1.522(3) ?
C10 C13 1.528(3) ?
C11 C12 1.518(3) ?
C12 C16 1.520(3) ?
C12 C15 1.529(3) ?
C13 H131 0.9600 ?
C13 H132 0.9600 ?
C13 H133 0.9600 ?
C14 H141 0.9600 ?
C14 H142 0.9600 ?
C14 H143 0.9600 ?
C15 H151 0.9600 ?
C15 H152 0.9600 ?
C15 H153 0.9600 ?
C16 H161 0.9600 ?
C16 H162 0.9600 ?
C16 H163 0.9600 ?
Cl21 C21 1.7796(16) yes
Cl22 C29 1.7863(16) yes
S21 C21 1.8176(16) yes
S21 S22 2.0361(7) yes
S22 S23 2.0681(7) yes
S23 S24 2.0336(7) yes
S24 C29 1.8172(16) yes
O21 C23 1.199(2) ?
O22 C31 1.200(2) ?
C21 C22 1.588(2) yes
C21 C24 1.587(2) yes
C22 C23 1.524(3) ?
C22 C25 1.524(3) ?
C22 C26 1.532(3) ?
C23 C24 1.517(3) ?
C24 C27 1.528(3) ?
C24 C28 1.528(3) ?
C25 H251 0.9600 ?
C25 H252 0.9600 ?
C25 H253 0.9600 ?
C26 H261 0.9600 ?
C26 H262 0.9600 ?
C26 H263 0.9600 ?
C27 H271 0.9600 ?
C27 H272 0.9600 ?
C27 H273 0.9600 ?
C28 H281 0.9600 ?
C28 H282 0.9600 ?
C28 H283 0.9600 ?
C29 C30 1.589(2) yes
C29 C32 1.587(2) yes
C30 C31 1.521(3) ?
C30 C34 1.523(3) ?
C30 C33 1.525(3) ?
C31 C32 1.517(2) ?
C32 C36 1.522(3) ?
C32 C35 1.529(3) ?
C33 H331 0.9600 ?
C33 H332 0.9600 ?
C33 H333 0.9600 ?
C34 H341 0.9600 ?
C34 H342 0.9600 ?
C34 H343 0.9600 ?
C35 H351 0.9600 ?
C35 H352 0.9600 ?
C35 H353 0.9600 ?
C36 H361 0.9600 ?
C36 H362 0.9600 ?
C36 H363 0.9600 ?
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_publ_flag
C1 S1 S2 S3 -99.07(6) yes
S1 S2 S3 S4 -92.44(3) yes
S2 S3 S4 C9 -96.10(6) yes
S2 S1 C1 C2 -174.87(10) ?
S2 S1 C1 C4 -72.75(12) ?
S2 S1 C1 Cl1 58.09(9) ?
C4 C1 C2 C3 0.09(14) ?
Cl1 C1 C2 C3 -117.19(13) ?
S1 C1 C2 C3 119.00(13) ?
C4 C1 C2 C6 -115.4(2) ?
Cl1 C1 C2 C6 127.32(18) ?
S1 C1 C2 C6 3.5(2) ?
C4 C1 C2 C5 113.35(19) ?
Cl1 C1 C2 C5 -3.9(2) ?
S1 C1 C2 C5 -127.73(18) ?
C6 C2 C3 O1 -62.6(4) ?
C5 C2 C3 O1 62.5(4) ?
C1 C2 C3 O1 179.6(3) ?
C6 C2 C3 C4 117.70(18) ?
C5 C2 C3 C4 -117.19(17) ?
C1 C2 C3 C4 -0.10(14) ?
O1 C3 C4 C7 -61.8(4) ?
C2 C3 C4 C7 117.9(2) ?
O1 C3 C4 C8 63.7(4) ?
C2 C3 C4 C8 -116.61(18) ?
O1 C3 C4 C1 -179.6(3) ?
C2 C3 C4 C1 0.10(14) ?
C2 C1 C4 C3 -0.09(14) ?
Cl1 C1 C4 C3 117.34(14) ?
S1 C1 C4 C3 -114.51(14) ?
C2 C1 C4 C7 -114.6(2) ?
Cl1 C1 C4 C7 2.8(2) ?
S1 C1 C4 C7 130.95(19) ?
C2 C1 C4 C8 111.3(2) ?
Cl1 C1 C4 C8 -131.25(19) ?
S1 C1 C4 C8 -3.1(2) ?
S3 S4 C9 C12 -175.16(11) ?
S3 S4 C9 C10 -71.66(13) ?
S3 S4 C9 Cl2 58.26(9) ?
C12 C9 C10 C11 -1.88(13) ?
Cl2 C9 C10 C11 114.73(13) ?
S4 C9 C10 C11 -117.65(13) ?
C12 C9 C10 C14 -117.10(18) ?
Cl2 C9 C10 C14 -0.5(2) ?
S4 C9 C10 C14 127.13(16) ?
C12 C9 C10 C13 109.89(18) ?
Cl2 C9 C10 C13 -133.50(17) ?
S4 C9 C10 C13 -5.9(2) ?
C14 C10 C11 O2 -59.9(3) ?
C13 C10 C11 O2 65.7(3) ?
C9 C10 C11 O2 -177.8(3) ?
C14 C10 C11 C12 119.92(18) ?
C13 C10 C11 C12 -114.56(17) ?
C9 C10 C11 C12 1.98(14) ?
O2 C11 C12 C16 60.2(3) ?
C10 C11 C12 C16 -119.57(18) ?
O2 C11 C12 C15 -65.2(3) ?
C10 C11 C12 C15 114.99(17) ?
O2 C11 C12 C9 177.8(3) ?
C10 C11 C12 C9 -1.98(14) ?
C10 C9 C12 C11 1.88(13) ?
Cl2 C9 C12 C11 -114.16(13) ?
S4 C9 C12 C11 122.31(13) ?
C10 C9 C12 C16 116.32(19) ?
Cl2 C9 C12 C16 0.3(2) ?
S4 C9 C12 C16 -123.25(18) ?
C10 C9 C12 C15 -112.46(18) ?
Cl2 C9 C12 C15 131.50(16) ?
S4 C9 C12 C15 8.0(2) ?
C21 S21 S22 S23 -98.25(6) yes
S21 S22 S23 S24 -94.27(3) yes
S22 S23 S24 C29 -96.40(6) yes
S22 S21 C21 C24 -72.78(12) ?
S22 S21 C21 C22 -173.93(10) ?
S22 S21 C21 Cl21 58.64(9) ?
C24 C21 C22 C23 -6.18(12) ?
Cl21 C21 C22 C23 -124.41(12) ?
S21 C21 C22 C23 112.04(12) ?
C24 C21 C22 C25 106.81(18) ?
Cl21 C21 C22 C25 -11.4(2) ?
S21 C21 C22 C25 -134.97(16) ?
C24 C21 C22 C26 -121.35(16) ?
Cl21 C21 C22 C26 120.42(15) ?
S21 C21 C22 C26 -3.13(19) ?
C25 C22 C23 O21 73.5(3) ?
C26 C22 C23 O21 -52.1(3) ?
C21 C22 C23 O21 -171.1(2) ?
C25 C22 C23 C24 -108.95(17) ?
C26 C22 C23 C24 125.50(16) ?
C21 C22 C23 C24 6.50(13) ?
O21 C23 C24 C27 -72.9(3) ?
C22 C23 C24 C27 109.53(17) ?
O21 C23 C24 C28 52.2(3) ?
C22 C23 C24 C28 -125.35(17) ?
O21 C23 C24 C21 171.1(2) ?
C22 C23 C24 C21 -6.51(13) ?
C22 C21 C24 C23 6.21(12) ?
Cl21 C21 C24 C23 124.98(12) ?
S21 C21 C24 C23 -106.56(13) ?
C22 C21 C24 C27 -106.34(18) ?
Cl21 C21 C24 C27 12.4(2) ?
S21 C21 C24 C27 140.90(17) ?
C22 C21 C24 C28 119.61(19) ?
Cl21 C21 C24 C28 -121.61(18) ?
S21 C21 C24 C28 6.8(2) ?
S23 S24 C29 C32 -173.96(10) ?
S23 S24 C29 C30 -71.72(13) ?
S23 S24 C29 Cl22 59.09(9) ?
C32 C29 C30 C31 2.59(12) ?
Cl22 C29 C30 C31 120.10(13) ?
S24 C29 C30 C31 -111.96(13) ?
C32 C29 C30 C34 -111.0(2) ?
Cl22 C29 C30 C34 6.5(2) ?
S24 C29 C30 C34 134.48(18) ?
C32 C29 C30 C33 115.61(19) ?
Cl22 C29 C30 C33 -126.88(18) ?
S24 C29 C30 C33 1.1(2) ?
C34 C30 C31 O22 -67.7(3) ?
C33 C30 C31 O22 57.6(3) ?
C29 C30 C31 O22 175.4(2) ?
C34 C30 C31 C32 114.17(18) ?
C33 C30 C31 C32 -120.51(16) ?
C29 C30 C31 C32 -2.73(13) ?
O22 C31 C32 C36 67.7(3) ?
C30 C31 C32 C36 -114.22(17) ?
O22 C31 C32 C35 -57.5(3) ?
C30 C31 C32 C35 120.62(16) ?
O22 C31 C32 C29 -175.4(2) ?
C30 C31 C32 C29 2.73(13) ?
C30 C29 C32 C31 -2.60(13) ?
Cl22 C29 C32 C31 -119.95(12) ?
S24 C29 C32 C31 116.56(12) ?
C30 C29 C32 C36 111.23(16) ?
Cl22 C29 C32 C36 -6.1(2) ?
S24 C29 C32 C36 -129.61(15) ?
C30 C29 C32 C35 -117.09(16) ?
Cl22 C29 C32 C35 125.56(15) ?
S24 C29 C32 C35 2.06(19) ?