#------------------------------------------------------------------------------
#$Date: 2021-02-04 02:39:27 +0200 (Thu, 04 Feb 2021) $
#$Revision: 261453 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/55/4135576.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_4135576
loop_
_publ_author_name
'Haut, Franz-Lucas'
'Habiger, Christoph'
'Wein, Lukas A.'
'Wurst, Klaus'
'Podewitz, Maren'
'Magauer, Thomas'
_publ_section_title
;
 Rapid Assembly of Tetrasubstituted Furans via Pummerer-Type
 Rearrangement.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1216
_journal_page_last               1223
_journal_paper_doi               10.1021/jacs.0c12194
_journal_volume                  143
_journal_year                    2021
_chemical_formula_sum            'C12 H18 O2 S'
_chemical_formula_weight         226.32
_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_method           SHELXL-2014/7
_cell_angle_alpha                108.4650(10)
_cell_angle_beta                 102.6140(10)
_cell_angle_gamma                98.5840(10)
_cell_formula_units_Z            8
_cell_length_a                   9.1402(4)
_cell_length_b                   15.4595(7)
_cell_length_c                   19.9824(9)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      23.8
_cell_measurement_theta_min      2.2
_cell_volume                     2539.8(2)
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_collection       'Bruker Apex III'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL-XT-2014/4 (Bruker AXS, 2014)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39037
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        22.998
_diffrn_reflns_theta_max         22.998
_diffrn_reflns_theta_min         2.241
_diffrn_source                   'Incoatec Microfocus'
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS-2014/5)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         7034
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0522
_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)+(0.0407P)²+2.7899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5246
_reflns_number_total             7034
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c12194_si_002.cif
_cod_data_source_block           11d
_cod_database_code               4135576
_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_min   0.963
_shelx_estimated_absorpt_t_max   0.988
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 0.42045(12) 0.87500(7) 0.58566(5) 0.0553(3) Uani 1 1 d . . . . .
S2 S 0.69525(11) 0.04545(7) 0.15396(6) 0.0508(3) Uani 1 1 d . . . . .
S3 S -0.10809(12) 0.11554(7) -0.07338(5) 0.0569(3) Uani 1 1 d . . . . .
S4 S 1.04118(12) 0.91937(8) 0.34918(6) 0.0649(3) Uani 1 1 d . . . . .
O1 O 0.5668(2) 0.57901(15) 0.35848(12) 0.0356(5) Uani 1 1 d D . . . .
H1O H 0.548(4) 0.5216(13) 0.3385(17) 0.043(11) Uiso 1 1 d D . . . .
O2 O 0.4971(3) 0.39338(15) 0.27800(13) 0.0365(5) Uani 1 1 d D . . . .
H2O H 0.470(4) 0.384(2) 0.2339(11) 0.045(11) Uiso 1 1 d D . . . .
O3 O 0.4095(3) 0.41373(16) 0.14519(12) 0.0379(6) Uani 1 1 d D . . . .
H3O H 0.437(3) 0.4704(13) 0.1602(16) 0.029(9) Uiso 1 1 d D . . . .
O4 O 0.5141(3) 0.59977(15) 0.22523(13) 0.0362(5) Uani 1 1 d D . . . .
H4O H 0.542(4) 0.608(2) 0.2692(11) 0.048(12) Uiso 1 1 d D . . . .
O11 O 0.6709(2) 0.85134(14) 0.53929(11) 0.0377(5) Uani 1 1 d . . . . .
O22 O 0.4239(2) 0.09160(14) 0.14779(11) 0.0387(6) Uani 1 1 d . . . . .
O33 O 0.1987(3) 0.13837(14) -0.02850(12) 0.0421(6) Uani 1 1 d . . . . .
O44 O 0.7519(3) 0.89329(15) 0.35926(12) 0.0433(6) Uani 1 1 d . . . . .
C1 C 0.3132(4) 0.9114(3) 0.5175(2) 0.0545(10) Uani 1 1 d . . . . .
H1A H 0.2489 0.9513 0.5390 0.082 Uiso 1 1 calc R U . . .
H1B H 0.3847 0.9467 0.5001 0.082 Uiso 1 1 calc R U . . .
H1C H 0.2472 0.8560 0.4761 0.082 Uiso 1 1 calc R U . . .
C2 C 0.6423(5) -0.0505(3) 0.1835(2) 0.0667(12) Uani 1 1 d . . . . .
H2A H 0.7010 -0.0976 0.1679 0.100 Uiso 1 1 calc R U . . .
H2B H 0.6655 -0.0270 0.2373 0.100 Uiso 1 1 calc R U . . .
H2C H 0.5317 -0.0791 0.1615 0.100 Uiso 1 1 calc R U . . .
C3 C -0.1617(4) 0.0823(2) -0.00195(19) 0.0461(9) Uani 1 1 d . . . . .
H3A H -0.2670 0.0429 -0.0212 0.069 Uiso 1 1 calc R U . . .
H3B H -0.0905 0.0471 0.0150 0.069 Uiso 1 1 calc R U . . .
H3C H -0.1569 0.1388 0.0393 0.069 Uiso 1 1 calc R U . . .
C4 C 1.0511(6) 0.9972(3) 0.3031(3) 0.1053(19) Uani 1 1 d . . . . .
H4A H 1.1573 1.0345 0.3180 0.158 Uiso 1 1 calc R U . . .
H4B H 1.0192 0.9621 0.2499 0.158 Uiso 1 1 calc R U . . .
H4C H 0.9824 1.0391 0.3152 0.158 Uiso 1 1 calc R U . . .
C11 C 0.6654(3) 0.6088(2) 0.43213(16) 0.0287(7) Uani 1 1 d . . . . .
H11 H 0.6378 0.5601 0.4532 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8389(3) 0.6229(2) 0.43678(17) 0.0329(8) Uani 1 1 d . . . . .
C13 C 0.8987(4) 0.7171(2) 0.42974(18) 0.0395(8) Uani 1 1 d . . . . .
H13A H 1.0082 0.7232 0.4300 0.047 Uiso 1 1 calc R U . . .
H13B H 0.8399 0.7167 0.3817 0.047 Uiso 1 1 calc R U . . .
C14 C 0.8860(4) 0.8030(2) 0.49081(18) 0.0383(8) Uani 1 1 d . . . . .
H14A H 0.9661 0.8156 0.5372 0.046 Uiso 1 1 calc R U . . .
H14B H 0.9003 0.8591 0.4769 0.046 Uiso 1 1 calc R U . . .
C15 C 0.7308(3) 0.7819(2) 0.50045(16) 0.0315(7) Uani 1 1 d . . . . .
C16 C 0.6318(3) 0.6979(2) 0.47588(15) 0.0265(7) Uani 1 1 d . . . . .
C17 C 0.4981(3) 0.7131(2) 0.49990(16) 0.0310(7) Uani 1 1 d . . . . .
C18 C 0.5253(4) 0.8061(2) 0.53789(17) 0.0360(8) Uani 1 1 d . . . . .
C19 C 0.8653(4) 0.5436(2) 0.37512(19) 0.0492(10) Uani 1 1 d . . . . .
H19A H 0.8110 0.5444 0.3273 0.074 Uiso 1 1 calc R U . . .
H19B H 0.9760 0.5523 0.3798 0.074 Uiso 1 1 calc R U . . .
H19C H 0.8258 0.4832 0.3787 0.074 Uiso 1 1 calc R U . . .
C20 C 0.9247(4) 0.6204(2) 0.51104(18) 0.0407(8) Uani 1 1 d . . . . .
H20A H 0.9087 0.6710 0.5510 0.061 Uiso 1 1 calc R U . . .
H20B H 0.8850 0.5598 0.5142 0.061 Uiso 1 1 calc R U . . .
H20C H 1.0352 0.6289 0.5153 0.061 Uiso 1 1 calc R U . . .
C21 C 0.4278(3) 0.3115(2) 0.28923(16) 0.0294(7) Uani 1 1 d . . . . .
H21 H 0.4752 0.3194 0.3415 0.035 Uiso 1 1 calc R U . . .
C22 C 0.2517(3) 0.2964(2) 0.27673(17) 0.0315(7) Uani 1 1 d . . . . .
C23 C 0.1669(3) 0.2534(2) 0.19421(17) 0.0352(8) Uani 1 1 d . . . . .
H23A H 0.0549 0.2476 0.1877 0.042 Uiso 1 1 calc R U . . .
H23B H 0.2014 0.2966 0.1702 0.042 Uiso 1 1 calc R U . . .
C24 C 0.1940(4) 0.1568(2) 0.15572(18) 0.0388(8) Uani 1 1 d . . . . .
H24A H 0.1309 0.1082 0.1669 0.047 Uiso 1 1 calc R U . . .
H24B H 0.1641 0.1408 0.1018 0.047 Uiso 1 1 calc R U . . .
C25 C 0.3592(4) 0.1606(2) 0.18274(16) 0.0318(8) Uani 1 1 d . . . . .
C26 C 0.4651(3) 0.2267(2) 0.24138(15) 0.0259(7) Uani 1 1 d . . . . .
C27 C 0.6089(3) 0.1988(2) 0.24476(17) 0.0304(7) Uani 1 1 d . . . . .
C28 C 0.5787(4) 0.1173(2) 0.18742(17) 0.0344(8) Uani 1 1 d . . . . .
C29 C 0.2117(4) 0.3902(2) 0.3109(2) 0.0487(9) Uani 1 1 d . . . . .
H29A H 0.2660 0.4175 0.3636 0.073 Uiso 1 1 calc R U . . .
H29B H 0.2434 0.4332 0.2869 0.073 Uiso 1 1 calc R U . . .
H29C H 0.1002 0.3800 0.3040 0.073 Uiso 1 1 calc R U . . .
C30 C 0.2035(4) 0.2298(2) 0.31543(18) 0.0414(9) Uani 1 1 d . . . . .
H30A H 0.2288 0.1696 0.2938 0.062 Uiso 1 1 calc R U . . .
H30B H 0.2588 0.2577 0.3680 0.062 Uiso 1 1 calc R U . . .
H30C H 0.0921 0.2197 0.3092 0.062 Uiso 1 1 calc R U . . .
C31 C 0.4213(4) 0.3809(2) 0.07095(16) 0.0331(8) Uani 1 1 d . . . . .
H31 H 0.3988 0.4286 0.0486 0.040 Uiso 1 1 calc R U . . .
C32 C 0.5815(4) 0.3648(2) 0.06636(17) 0.0386(8) Uani 1 1 d . . . . .
C33 C 0.6000(4) 0.2729(2) 0.07841(18) 0.0432(9) Uani 1 1 d . . . . .
H33A H 0.7057 0.2655 0.0783 0.052 Uiso 1 1 calc R U . . .
H33B H 0.5886 0.2779 0.1275 0.052 Uiso 1 1 calc R U . . .
C34 C 0.4842(4) 0.1853(2) 0.02061(19) 0.0448(9) Uani 1 1 d . . . . .
H34A H 0.5139 0.1675 -0.0258 0.054 Uiso 1 1 calc R U . . .
H34B H 0.4818 0.1321 0.0382 0.054 Uiso 1 1 calc R U . . .
C35 C 0.3315(4) 0.2073(2) 0.00824(17) 0.0353(8) Uani 1 1 d . . . . .
C36 C 0.2994(4) 0.2922(2) 0.02905(16) 0.0308(7) Uani 1 1 d . . . . .
C37 C 0.1356(4) 0.2781(2) 0.00486(17) 0.0348(8) Uani 1 1 d . . . . .
C38 C 0.0790(4) 0.1840(2) -0.02946(17) 0.0410(9) Uani 1 1 d . . . . .
C39 C 0.7078(4) 0.4461(3) 0.1248(2) 0.0593(11) Uani 1 1 d . . . . .
H39A H 0.7001 0.4498 0.1738 0.089 Uiso 1 1 calc R U . . .
H39B H 0.8090 0.4358 0.1203 0.089 Uiso 1 1 calc R U . . .
H39C H 0.6955 0.5048 0.1180 0.089 Uiso 1 1 calc R U . . .
C40 C 0.5937(4) 0.3589(3) -0.0102(2) 0.0532(10) Uani 1 1 d . . . . .
H40A H 0.5125 0.3067 -0.0478 0.080 Uiso 1 1 calc R U . . .
H40B H 0.5813 0.4177 -0.0171 0.080 Uiso 1 1 calc R U . . .
H40C H 0.6949 0.3487 -0.0147 0.080 Uiso 1 1 calc R U . . .
C41 C 0.4815(3) 0.6846(2) 0.21745(17) 0.0308(7) Uani 1 1 d . . . . .
H41 H 0.4695 0.6775 0.1649 0.037 Uiso 1 1 calc R U . . .
C42 C 0.3309(4) 0.7049(2) 0.23513(17) 0.0351(8) Uani 1 1 d . . . . .
C43 C 0.3594(4) 0.7471(2) 0.31885(18) 0.0404(8) Uani 1 1 d . . . . .
H43A H 0.2608 0.7568 0.3293 0.048 Uiso 1 1 calc R U . . .
H43B H 0.3931 0.7015 0.3405 0.048 Uiso 1 1 calc R U . . .
C44 C 0.4800(4) 0.8401(2) 0.35621(19) 0.0427(9) Uani 1 1 d . . . . .
H44A H 0.4355 0.8915 0.3474 0.051 Uiso 1 1 calc R U . . .
H44B H 0.5145 0.8549 0.4099 0.051 Uiso 1 1 calc R U . . .
C45 C 0.6120(4) 0.8310(2) 0.32491(17) 0.0341(8) Uani 1 1 d . . . . .
C46 C 0.6158(3) 0.7647(2) 0.26330(16) 0.0280(7) Uani 1 1 d . . . . .
C47 C 0.7692(4) 0.7841(2) 0.25708(18) 0.0346(8) Uani 1 1 d . . . . .
C48 C 0.8480(4) 0.8613(2) 0.31578(19) 0.0402(8) Uani 1 1 d . . . . .
C49 C 0.2053(4) 0.6139(3) 0.2029(2) 0.0559(10) Uani 1 1 d . . . . .
H49A H 0.2369 0.5696 0.2258 0.084 Uiso 1 1 calc R U . . .
H49B H 0.1088 0.6273 0.2125 0.084 Uiso 1 1 calc R U . . .
H49C H 0.1896 0.5863 0.1497 0.084 Uiso 1 1 calc R U . . .
C50 C 0.2814(4) 0.7739(3) 0.1992(2) 0.0501(10) Uani 1 1 d . . . . .
H50A H 0.3619 0.8323 0.2199 0.075 Uiso 1 1 calc R U . . .
H50B H 0.2657 0.7463 0.1460 0.075 Uiso 1 1 calc R U . . .
H50C H 0.1849 0.7873 0.2088 0.075 Uiso 1 1 calc R U . . .
C171 C 0.3561(4) 0.6400(2) 0.48554(19) 0.0446(9) Uani 1 1 d . . . . .
H17A H 0.2849 0.6692 0.5103 0.067 Uiso 1 1 calc R U . . .
H17B H 0.3845 0.5917 0.5044 0.067 Uiso 1 1 calc R U . . .
H17C H 0.3060 0.6113 0.4325 0.067 Uiso 1 1 calc R U . . .
C271 C 0.7607(4) 0.2504(3) 0.3003(2) 0.0500(10) Uani 1 1 d . . . . .
H27A H 0.8353 0.2112 0.2943 0.075 Uiso 1 1 calc R U . . .
H27B H 0.7483 0.2653 0.3499 0.075 Uiso 1 1 calc R U . . .
H27C H 0.7982 0.3087 0.2931 0.075 Uiso 1 1 calc R U . . .
C371 C 0.0466(4) 0.3517(3) 0.0165(2) 0.0581(11) Uani 1 1 d . . . . .
H37A H -0.0635 0.3227 -0.0071 0.087 Uiso 1 1 calc R U . . .
H37B H 0.0809 0.3971 -0.0051 0.087 Uiso 1 1 calc R U . . .
H37C H 0.0636 0.3841 0.0694 0.087 Uiso 1 1 calc R U . . .
C471 C 0.8292(4) 0.7295(3) 0.1973(2) 0.0560(10) Uani 1 1 d . . . . .
H47A H 0.9362 0.7608 0.2051 0.084 Uiso 1 1 calc R U . . .
H47B H 0.7659 0.7259 0.1496 0.084 Uiso 1 1 calc R U . . .
H47C H 0.8248 0.6660 0.1978 0.084 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'
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
C18 S1 C1 102.68(16) . . ?
C28 S2 C2 100.66(17) . . ?
C38 S3 C3 102.82(16) . . ?
C48 S4 C4 102.4(2) . . ?
C11 O1 H1O 110(2) . . ?
C21 O2 H2O 108(2) . . ?
C31 O3 H3O 106(2) . . ?
C41 O4 H4O 109(2) . . ?
C15 O11 C18 105.6(2) . . ?
C25 O22 C28 105.9(2) . . ?
C35 O33 C38 105.9(2) . . ?
C45 O44 C48 105.2(2) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
S2 C2 H2A 109.5 . . ?
S2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
S2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
S3 C3 H3A 109.5 . . ?
S3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
S3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
S4 C4 H4A 109.5 . . ?
S4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
S4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C11 C16 107.3(2) . . ?
O1 C11 C12 113.5(2) . . ?
C16 C11 C12 110.8(2) . . ?
O1 C11 H11 108.4 . . ?
C16 C11 H11 108.4 . . ?
C12 C11 H11 108.4 . . ?
C19 C12 C20 108.7(3) . . ?
C19 C12 C13 109.0(3) . . ?
C20 C12 C13 110.9(3) . . ?
C19 C12 C11 110.4(3) . . ?
C20 C12 C11 107.8(2) . . ?
C13 C12 C11 110.0(3) . . ?
C14 C13 C12 114.1(3) . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 107.2(3) . . ?
C15 C14 H14A 110.3 . . ?
C13 C14 H14A 110.3 . . ?
C15 C14 H14B 110.3 . . ?
C13 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
C16 C15 O11 111.0(3) . . ?
C16 C15 C14 127.7(3) . . ?
O11 C15 C14 121.4(3) . . ?
C15 C16 C17 106.9(3) . . ?
C15 C16 C11 123.2(3) . . ?
C17 C16 C11 129.9(3) . . ?
C18 C17 C16 106.6(3) . . ?
C18 C17 C171 126.9(3) . . ?
C16 C17 C171 126.5(3) . . ?
C17 C18 O11 109.9(3) . . ?
C17 C18 S1 132.9(3) . . ?
O11 C18 S1 117.1(2) . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 C26 110.0(2) . . ?
O2 C21 C22 113.8(2) . . ?
C26 C21 C22 110.3(2) . . ?
O2 C21 H21 107.5 . . ?
C26 C21 H21 107.5 . . ?
C22 C21 H21 107.5 . . ?
C29 C22 C23 109.6(3) . . ?
C29 C22 C30 109.1(3) . . ?
C23 C22 C30 110.2(3) . . ?
C29 C22 C21 109.8(3) . . ?
C23 C22 C21 110.5(2) . . ?
C30 C22 C21 107.5(2) . . ?
C24 C23 C22 113.5(2) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C23 108.0(3) . . ?
C25 C24 H24A 110.1 . . ?
C23 C24 H24A 110.1 . . ?
C25 C24 H24B 110.1 . . ?
C23 C24 H24B 110.1 . . ?
H24A C24 H24B 108.4 . . ?
C26 C25 O22 110.8(3) . . ?
C26 C25 C24 128.0(3) . . ?
O22 C25 C24 121.2(3) . . ?
C25 C26 C27 106.9(3) . . ?
C25 C26 C21 122.6(3) . . ?
C27 C26 C21 130.5(3) . . ?
C28 C27 C26 106.0(3) . . ?
C28 C27 C271 127.2(3) . . ?
C26 C27 C271 126.7(3) . . ?
C27 C28 O22 110.4(3) . . ?
C27 C28 S2 132.6(3) . . ?
O22 C28 S2 117.0(2) . . ?
C22 C29 H29A 109.5 . . ?
C22 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C22 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C22 C30 H30A 109.5 . . ?
C22 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C22 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O3 C31 C36 107.2(2) . . ?
O3 C31 C32 113.4(2) . . ?
C36 C31 C32 110.8(3) . . ?
O3 C31 H31 108.5 . . ?
C36 C31 H31 108.5 . . ?
C32 C31 H31 108.5 . . ?
C39 C32 C40 109.5(3) . . ?
C39 C32 C31 110.4(3) . . ?
C40 C32 C31 107.7(3) . . ?
C39 C32 C33 109.1(3) . . ?
C40 C32 C33 110.5(3) . . ?
C31 C32 C33 109.7(3) . . ?
C34 C33 C32 114.0(3) . . ?
C34 C33 H33A 108.7 . . ?
C32 C33 H33A 108.7 . . ?
C34 C33 H33B 108.7 . . ?
C32 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?
C35 C34 C33 107.6(3) . . ?
C35 C34 H34A 110.2 . . ?
C33 C34 H34A 110.2 . . ?
C35 C34 H34B 110.2 . . ?
C33 C34 H34B 110.2 . . ?
H34A C34 H34B 108.5 . . ?
C36 C35 O33 110.7(3) . . ?
C36 C35 C34 127.8(3) . . ?
O33 C35 C34 121.6(3) . . ?
C35 C36 C37 107.3(3) . . ?
C35 C36 C31 122.8(3) . . ?
C37 C36 C31 129.9(3) . . ?
C38 C37 C36 106.0(3) . . ?
C38 C37 C371 127.4(3) . . ?
C36 C37 C371 126.6(3) . . ?
C37 C38 O33 110.2(3) . . ?
C37 C38 S3 132.1(3) . . ?
O33 C38 S3 117.7(2) . . ?
C32 C39 H39A 109.5 . . ?
C32 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C32 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C32 C40 H40A 109.5 . . ?
C32 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C32 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O4 C41 C46 109.5(2) . . ?
O4 C41 C42 113.8(2) . . ?
C46 C41 C42 111.1(3) . . ?
O4 C41 H41 107.4 . . ?
C46 C41 H41 107.4 . . ?
C42 C41 H41 107.4 . . ?
C49 C42 C50 109.4(3) . . ?
C49 C42 C43 109.7(3) . . ?
C50 C42 C43 110.7(3) . . ?
C49 C42 C41 109.6(3) . . ?
C50 C42 C41 107.6(3) . . ?
C43 C42 C41 109.8(3) . . ?
C44 C43 C42 113.9(3) . . ?
C44 C43 H43A 108.8 . . ?
C42 C43 H43A 108.8 . . ?
C44 C43 H43B 108.8 . . ?
C42 C43 H43B 108.8 . . ?
H43A C43 H43B 107.7 . . ?
C45 C44 C43 108.0(3) . . ?
C45 C44 H44A 110.1 . . ?
C43 C44 H44A 110.1 . . ?
C45 C44 H44B 110.1 . . ?
C43 C44 H44B 110.1 . . ?
H44A C44 H44B 108.4 . . ?
C46 C45 O44 111.1(3) . . ?
C46 C45 C44 127.7(3) . . ?
O44 C45 C44 121.2(3) . . ?
C45 C46 C47 107.0(3) . . ?
C45 C46 C41 122.5(3) . . ?
C47 C46 C41 130.3(3) . . ?
C48 C47 C46 106.2(3) . . ?
C48 C47 C471 127.1(3) . . ?
C46 C47 C471 126.8(3) . . ?
C47 C48 O44 110.4(3) . . ?
C47 C48 S4 132.5(3) . . ?
O44 C48 S4 116.9(2) . . ?
C42 C49 H49A 109.5 . . ?
C42 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C42 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C42 C50 H50A 109.5 . . ?
C42 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C42 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C17 C171 H17A 109.5 . . ?
C17 C171 H17B 109.5 . . ?
H17A C171 H17B 109.5 . . ?
C17 C171 H17C 109.5 . . ?
H17A C171 H17C 109.5 . . ?
H17B C171 H17C 109.5 . . ?
C27 C271 H27A 109.5 . . ?
C27 C271 H27B 109.5 . . ?
H27A C271 H27B 109.5 . . ?
C27 C271 H27C 109.5 . . ?
H27A C271 H27C 109.5 . . ?
H27B C271 H27C 109.5 . . ?
C37 C371 H37A 109.5 . . ?
C37 C371 H37B 109.5 . . ?
H37A C371 H37B 109.5 . . ?
C37 C371 H37C 109.5 . . ?
H37A C371 H37C 109.5 . . ?
H37B C371 H37C 109.5 . . ?
C47 C471 H47A 109.5 . . ?
C47 C471 H47B 109.5 . . ?
H47A C471 H47B 109.5 . . ?
C47 C471 H47C 109.5 . . ?
H47A C471 H47C 109.5 . . ?
H47B C471 H47C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C18 1.739(3) . ?
S1 C1 1.789(4) . ?
S2 C28 1.735(3) . ?
S2 C2 1.802(4) . ?
S3 C38 1.740(3) . ?
S3 C3 1.799(4) . ?
S4 C48 1.733(3) . ?
S4 C4 1.736(5) . ?
O1 C11 1.435(3) . ?
O1 H1O 0.822(18) . ?
O2 C21 1.434(4) . ?
O2 H2O 0.820(18) . ?
O3 C31 1.442(4) . ?
O3 H3O 0.810(17) . ?
O4 C41 1.434(4) . ?
O4 H4O 0.821(18) . ?
O11 C15 1.374(4) . ?
O11 C18 1.398(4) . ?
O22 C25 1.368(4) . ?
O22 C28 1.389(4) . ?
O33 C35 1.370(4) . ?
O33 C38 1.387(4) . ?
O44 C45 1.365(4) . ?
O44 C48 1.401(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C11 C16 1.495(4) . ?
C11 C12 1.546(4) . ?
C11 H11 1.0000 . ?
C12 C19 1.531(4) . ?
C12 C20 1.535(4) . ?
C12 C13 1.538(4) . ?
C13 C14 1.532(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.475(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.341(4) . ?
C16 C17 1.432(4) . ?
C17 C18 1.351(4) . ?
C17 C171 1.496(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.494(4) . ?
C21 C22 1.544(4) . ?
C21 H21 1.0000 . ?
C22 C29 1.531(4) . ?
C22 C23 1.535(4) . ?
C22 C30 1.540(4) . ?
C23 C24 1.534(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.473(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.344(4) . ?
C26 C27 1.437(4) . ?
C27 C28 1.349(4) . ?
C27 C271 1.493(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C36 1.494(4) . ?
C31 C32 1.540(4) . ?
C31 H31 1.0000 . ?
C32 C39 1.525(5) . ?
C32 C40 1.534(4) . ?
C32 C33 1.540(5) . ?
C33 C34 1.529(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.473(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.342(4) . ?
C36 C37 1.429(4) . ?
C37 C38 1.358(4) . ?
C37 C371 1.485(5) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 C46 1.489(4) . ?
C41 C42 1.546(4) . ?
C41 H41 1.0000 . ?
C42 C49 1.528(5) . ?
C42 C50 1.531(4) . ?
C42 C43 1.536(4) . ?
C43 C44 1.526(5) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.480(4) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.340(4) . ?
C46 C47 1.431(4) . ?
C47 C48 1.344(4) . ?
C47 C471 1.492(5) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C171 H17A 0.9800 . ?
C171 H17B 0.9800 . ?
C171 H17C 0.9800 . ?
C271 H27A 0.9800 . ?
C271 H27B 0.9800 . ?
C271 H27C 0.9800 . ?
C371 H37A 0.9800 . ?
C371 H37B 0.9800 . ?
C371 H37C 0.9800 . ?
C471 H47A 0.9800 . ?
C471 H47B 0.9800 . ?
C471 H47C 0.9800 . ?
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
O1 H1O O2 0.822(18) 1.890(19) 2.704(3) 171(3) .
O2 H2O O3 0.820(18) 1.95(2) 2.731(3) 158(3) .
O3 H3O O4 0.810(17) 1.93(2) 2.709(3) 162(3) .
O4 H4O O1 0.821(18) 1.95(2) 2.730(3) 159(3) .
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
O1 C11 C12 C19 -42.0(3) . . . . ?
C16 C11 C12 C19 -162.8(3) . . . . ?
O1 C11 C12 C20 -160.6(2) . . . . ?
C16 C11 C12 C20 78.6(3) . . . . ?
O1 C11 C12 C13 78.3(3) . . . . ?
C16 C11 C12 C13 -42.4(3) . . . . ?
C19 C12 C13 C14 -177.2(3) . . . . ?
C20 C12 C13 C14 -57.6(4) . . . . ?
C11 C12 C13 C14 61.6(3) . . . . ?
C12 C13 C14 C15 -45.4(4) . . . . ?
C18 O11 C15 C16 -0.2(3) . . . . ?
C18 O11 C15 C14 -179.2(3) . . . . ?
C13 C14 C15 C16 15.5(4) . . . . ?
C13 C14 C15 O11 -165.6(3) . . . . ?
O11 C15 C16 C17 0.2(3) . . . . ?
C14 C15 C16 C17 179.2(3) . . . . ?
O11 C15 C16 C11 -179.7(2) . . . . ?
C14 C15 C16 C11 -0.7(5) . . . . ?
O1 C11 C16 C15 -109.9(3) . . . . ?
C12 C11 C16 C15 14.5(4) . . . . ?
O1 C11 C16 C17 70.3(4) . . . . ?
C12 C11 C16 C17 -165.3(3) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C11 C16 C17 C18 179.7(3) . . . . ?
C15 C16 C17 C171 179.9(3) . . . . ?
C11 C16 C17 C171 -0.3(5) . . . . ?
C16 C17 C18 O11 0.0(3) . . . . ?
C171 C17 C18 O11 -180.0(3) . . . . ?
C16 C17 C18 S1 -177.2(3) . . . . ?
C171 C17 C18 S1 2.8(5) . . . . ?
C15 O11 C18 C17 0.1(3) . . . . ?
C15 O11 C18 S1 177.8(2) . . . . ?
C1 S1 C18 C17 -92.6(4) . . . . ?
C1 S1 C18 O11 90.3(3) . . . . ?
O2 C21 C22 C29 -42.2(3) . . . . ?
C26 C21 C22 C29 -166.3(3) . . . . ?
O2 C21 C22 C23 78.9(3) . . . . ?
C26 C21 C22 C23 -45.2(3) . . . . ?
O2 C21 C22 C30 -160.8(2) . . . . ?
C26 C21 C22 C30 75.2(3) . . . . ?
C29 C22 C23 C24 -177.3(3) . . . . ?
C30 C22 C23 C24 -57.3(3) . . . . ?
C21 C22 C23 C24 61.5(3) . . . . ?
C22 C23 C24 C25 -43.0(4) . . . . ?
C28 O22 C25 C26 -0.1(3) . . . . ?
C28 O22 C25 C24 180.0(3) . . . . ?
C23 C24 C25 C26 13.7(4) . . . . ?
C23 C24 C25 O22 -166.4(3) . . . . ?
O22 C25 C26 C27 0.1(3) . . . . ?
C24 C25 C26 C27 180.0(3) . . . . ?
O22 C25 C26 C21 178.8(2) . . . . ?
C24 C25 C26 C21 -1.3(5) . . . . ?
O2 C21 C26 C25 -109.1(3) . . . . ?
C22 C21 C26 C25 17.2(4) . . . . ?
O2 C21 C26 C27 69.4(4) . . . . ?
C22 C21 C26 C27 -164.3(3) . . . . ?
C25 C26 C27 C28 0.0(3) . . . . ?
C21 C26 C27 C28 -178.6(3) . . . . ?
C25 C26 C27 C271 179.5(3) . . . . ?
C21 C26 C27 C271 0.9(5) . . . . ?
C26 C27 C28 O22 -0.1(3) . . . . ?
C271 C27 C28 O22 -179.6(3) . . . . ?
C26 C27 C28 S2 176.7(3) . . . . ?
C271 C27 C28 S2 -2.8(5) . . . . ?
C25 O22 C28 C27 0.1(3) . . . . ?
C25 O22 C28 S2 -177.2(2) . . . . ?
C2 S2 C28 C27 105.9(3) . . . . ?
C2 S2 C28 O22 -77.5(3) . . . . ?
O3 C31 C32 C39 -44.1(4) . . . . ?
C36 C31 C32 C39 -164.6(3) . . . . ?
O3 C31 C32 C40 -163.5(3) . . . . ?
C36 C31 C32 C40 76.0(3) . . . . ?
O3 C31 C32 C33 76.2(3) . . . . ?
C36 C31 C32 C33 -44.4(3) . . . . ?
C39 C32 C33 C34 -177.2(3) . . . . ?
C40 C32 C33 C34 -56.8(4) . . . . ?
C31 C32 C33 C34 61.8(4) . . . . ?
C32 C33 C34 C35 -44.1(4) . . . . ?
C38 O33 C35 C36 -0.6(3) . . . . ?
C38 O33 C35 C34 179.6(3) . . . . ?
C33 C34 C35 C36 14.2(5) . . . . ?
C33 C34 C35 O33 -166.1(3) . . . . ?
O33 C35 C36 C37 0.3(3) . . . . ?
C34 C35 C36 C37 -179.9(3) . . . . ?
O33 C35 C36 C31 179.3(3) . . . . ?
C34 C35 C36 C31 -0.9(5) . . . . ?
O3 C31 C36 C35 -107.6(3) . . . . ?
C32 C31 C36 C35 16.5(4) . . . . ?
O3 C31 C36 C37 71.2(4) . . . . ?
C32 C31 C36 C37 -164.7(3) . . . . ?
C35 C36 C37 C38 0.1(4) . . . . ?
C31 C36 C37 C38 -178.8(3) . . . . ?
C35 C36 C37 C371 179.0(3) . . . . ?
C31 C36 C37 C371 0.1(5) . . . . ?
C36 C37 C38 O33 -0.4(4) . . . . ?
C371 C37 C38 O33 -179.3(3) . . . . ?
C36 C37 C38 S3 -179.0(3) . . . . ?
C371 C37 C38 S3 2.1(6) . . . . ?
C35 O33 C38 C37 0.6(3) . . . . ?
C35 O33 C38 S3 179.4(2) . . . . ?
C3 S3 C38 C37 -94.8(4) . . . . ?
C3 S3 C38 O33 86.7(3) . . . . ?
O4 C41 C42 C49 -41.2(4) . . . . ?
C46 C41 C42 C49 -165.4(3) . . . . ?
O4 C41 C42 C50 -160.1(3) . . . . ?
C46 C41 C42 C50 75.7(3) . . . . ?
O4 C41 C42 C43 79.3(3) . . . . ?
C46 C41 C42 C43 -44.8(3) . . . . ?
C49 C42 C43 C44 -178.3(3) . . . . ?
C50 C42 C43 C44 -57.4(4) . . . . ?
C41 C42 C43 C44 61.3(3) . . . . ?
C42 C43 C44 C45 -44.1(4) . . . . ?
C48 O44 C45 C46 -1.0(3) . . . . ?
C48 O44 C45 C44 178.2(3) . . . . ?
C43 C44 C45 C46 15.4(5) . . . . ?
C43 C44 C45 O44 -163.7(3) . . . . ?
O44 C45 C46 C47 0.7(3) . . . . ?
C44 C45 C46 C47 -178.5(3) . . . . ?
O44 C45 C46 C41 176.2(3) . . . . ?
C44 C45 C46 C41 -3.0(5) . . . . ?
O4 C41 C46 C45 -108.6(3) . . . . ?
C42 C41 C46 C45 18.0(4) . . . . ?
O4 C41 C46 C47 65.8(4) . . . . ?
C42 C41 C46 C47 -167.6(3) . . . . ?
C45 C46 C47 C48 0.0(3) . . . . ?
C41 C46 C47 C48 -175.1(3) . . . . ?
C45 C46 C47 C471 -179.9(3) . . . . ?
C41 C46 C47 C471 5.1(5) . . . . ?
C46 C47 C48 O44 -0.6(4) . . . . ?
C471 C47 C48 O44 179.2(3) . . . . ?
C46 C47 C48 S4 173.5(3) . . . . ?
C471 C47 C48 S4 -6.7(6) . . . . ?
C45 O44 C48 C47 1.0(3) . . . . ?
C45 O44 C48 S4 -174.1(2) . . . . ?
C4 S4 C48 C47 88.6(4) . . . . ?
C4 S4 C48 O44 -97.6(3) . . . . ?
