#------------------------------------------------------------------------------
#$Date: 2021-07-03 04:09:33 +0300 (Sat, 03 Jul 2021) $
#$Revision: 266921 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/39/1563906.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_1563906
loop_
_publ_author_name
'Trost, Barry M.'
'Jiao, Zhiwei'
'Gholami, Hadi'
_publ_section_title
;
 Palladium-Catalyzed Asymmetric Allylic Alkylation (AAA) with Alkyl
 Sulfones as Nucleophiles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02599F
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 N O2 S'
_chemical_formula_sum            'C18 H19 N O2 S'
_chemical_formula_weight         313.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-11 deposited with the CCDC.	2021-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.270(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1212(5)
_cell_length_b                   8.4842(4)
_cell_length_c                   20.1475(10)
_cell_measurement_reflns_used    9222
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.29
_cell_measurement_theta_min      4.39
_cell_volume                     1559.12(14)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32783
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.362
_diffrn_reflns_theta_min         2.193
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    1.894
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6885
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       tablet
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2461 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.046(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5761
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0258
_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)+(0.0345P)²+0.2927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0652
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                5643
_reflns_number_total             5761
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02599f2.cif
_cod_data_source_block           zjd783
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1563906
_shelx_shelxl_version_number     2018/3
_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   0.641
_shelx_estimated_absorpt_t_max   0.901
_diffrn_source_monochromator     'MONTEL Multi-layer'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.83742(5) 0.19460(6) 0.85269(2) 0.02007(12) Uani 1 1 d . . . . .
O1 O 0.93901(16) 0.08867(19) 0.88459(8) 0.0296(4) Uani 1 1 d . . . . .
O2 O 0.82503(16) 0.1885(2) 0.78153(7) 0.0289(3) Uani 1 1 d . . . . .
N1 N 0.90717(19) 0.4177(2) 0.93891(9) 0.0248(4) Uani 1 1 d . . . . .
C2 C 0.8870(2) 0.3931(3) 0.87398(10) 0.0218(4) Uani 1 1 d . . . . .
C3 C 0.9050(2) 0.5032(3) 0.82454(11) 0.0295(5) Uani 1 1 d . . . . .
H3 H 0.889407 0.477623 0.779150 0.035 Uiso 1 1 calc R U . . .
C4 C 0.9473(3) 0.6543(3) 0.84420(12) 0.0353(5) Uani 1 1 d . . . . .
H4 H 0.961267 0.735142 0.812232 0.042 Uiso 1 1 calc R U . . .
C5 C 0.9686(2) 0.6842(3) 0.91093(12) 0.0328(5) Uani 1 1 d . . . . .
H5 H 0.997213 0.786203 0.925523 0.039 Uiso 1 1 calc R U . . .
C6 C 0.9477(2) 0.5636(3) 0.95640(11) 0.0290(5) Uani 1 1 d . . . . .
H6 H 0.962804 0.585627 1.002149 0.035 Uiso 1 1 calc R U . . .
C7 C 0.6625(2) 0.1697(2) 0.89047(9) 0.0203(4) Uani 1 1 d . . . . .
H7A H 0.670360 0.195537 0.938275 0.024 Uiso 1 1 calc R U . . .
H7B H 0.591927 0.244123 0.870042 0.024 Uiso 1 1 calc R U . . .
C8 C 0.6041(2) 0.0001(2) 0.88268(9) 0.0201(4) Uani 1 1 d . . . . .
H8 H 0.687930 -0.074037 0.889721 0.024 Uiso 1 1 calc R U . . .
C9 C 0.4916(2) -0.0303(2) 0.93704(9) 0.0200(4) Uani 1 1 d . . . . .
C10 C 0.3512(2) -0.0604(3) 0.92327(10) 0.0230(4) Uani 1 1 d . . . . .
H10 H 0.288715 -0.085774 0.959310 0.028 Uiso 1 1 calc R U . . .
C11 C 0.2847(2) -0.0573(3) 0.85484(10) 0.0265(5) Uani 1 1 d . . . . .
H11A H 0.187968 -0.004575 0.856508 0.032 Uiso 1 1 calc R U . . .
H11B H 0.269330 -0.166657 0.839118 0.032 Uiso 1 1 calc R U . . .
C12 C 0.3836(2) 0.0298(3) 0.80634(10) 0.0273(5) Uani 1 1 d . . . . .
H12A H 0.380636 0.144302 0.815735 0.033 Uiso 1 1 calc R U . . .
H12B H 0.347942 0.012921 0.760394 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5407(2) -0.0301(3) 0.81287(10) 0.0244(4) Uani 1 1 d . . . . .
H13A H 0.602823 0.023251 0.779559 0.029 Uiso 1 1 calc R U . . .
H13B H 0.542806 -0.144616 0.803517 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5446(2) -0.0267(2) 1.00712(10) 0.0218(4) Uani 1 1 d . . . . .
C15 C 0.6773(2) -0.0960(3) 1.02633(11) 0.0293(5) Uani 1 1 d . . . . .
H15 H 0.737488 -0.145171 0.994031 0.035 Uiso 1 1 calc R U . . .
C16 C 0.7215(3) -0.0934(4) 1.09252(12) 0.0396(6) Uani 1 1 d . . . . .
H16 H 0.810348 -0.143530 1.105299 0.047 Uiso 1 1 calc R U . . .
C17 C 0.6371(3) -0.0184(4) 1.13988(12) 0.0411(7) Uani 1 1 d . . . . .
H17 H 0.669229 -0.014348 1.184776 0.049 Uiso 1 1 calc R U . . .
C18 C 0.5062(3) 0.0505(3) 1.12151(11) 0.0353(6) Uani 1 1 d . . . . .
H18 H 0.447283 0.100670 1.154000 0.042 Uiso 1 1 calc R U . . .
C19 C 0.4601(3) 0.0468(3) 1.05571(11) 0.0278(5) Uani 1 1 d . . . . .
H19 H 0.369806 0.094966 1.043623 0.033 Uiso 1 1 calc R U . . .
S1A S 0.16105(5) 0.62554(6) 0.65180(2) 0.02151(12) Uani 1 1 d . . . . .
O1A O 0.04295(17) 0.5186(2) 0.63633(8) 0.0318(4) Uani 1 1 d . . . . .
O2A O 0.20360(19) 0.6425(2) 0.72026(7) 0.0353(4) Uani 1 1 d . . . . .
N1A N 0.08821(18) 0.8318(2) 0.55833(8) 0.0219(4) Uani 1 1 d . . . . .
C2A C 0.1080(2) 0.8183(2) 0.62373(10) 0.0207(4) Uani 1 1 d . . . . .
C3A C 0.0809(2) 0.9342(3) 0.67010(10) 0.0248(4) Uani 1 1 d . . . . .
H3A H 0.099303 0.917218 0.715995 0.030 Uiso 1 1 calc R U . . .
C4A C 0.0255(2) 1.0770(3) 0.64700(12) 0.0287(5) Uani 1 1 d . . . . .
H4A H 0.003231 1.159971 0.676953 0.034 Uiso 1 1 calc R U . . .
C5A C 0.0037(2) 1.0953(3) 0.57954(11) 0.0270(5) Uani 1 1 d . . . . .
H5A H -0.033796 1.191501 0.562328 0.032 Uiso 1 1 calc R U . . .
C6A C 0.0372(2) 0.9715(3) 0.53718(10) 0.0253(4) Uani 1 1 d . . . . .
H6A H 0.023388 0.986494 0.490846 0.030 Uiso 1 1 calc R U . . .
C7A C 0.3149(2) 0.5741(3) 0.60210(10) 0.0219(4) Uani 1 1 d . . . . .
H7AA H 0.293936 0.601901 0.555285 0.026 Uiso 1 1 calc R U . . .
H7AB H 0.401036 0.636249 0.616756 0.026 Uiso 1 1 calc R U . . .
C8A C 0.3520(2) 0.3968(2) 0.60651(10) 0.0212(4) Uani 1 1 d . . . . .
H8A H 0.262744 0.335660 0.593408 0.025 Uiso 1 1 calc R U . . .
C9A C 0.4710(2) 0.3652(2) 0.55535(10) 0.0205(4) Uani 1 1 d . . . . .
C10A C 0.6100(2) 0.3421(3) 0.57366(10) 0.0234(4) Uani 1 1 d . . . . .
H10A H 0.679525 0.324916 0.539441 0.028 Uiso 1 1 calc R U . . .
C11A C 0.6659(2) 0.3411(3) 0.64392(11) 0.0286(5) Uani 1 1 d . . . . .
H11C H 0.754942 0.407416 0.646827 0.034 Uiso 1 1 calc R U . . .
H11D H 0.693747 0.232109 0.656213 0.034 Uiso 1 1 calc R U . . .
C12A C 0.5522(3) 0.4021(3) 0.69339(10) 0.0307(5) Uani 1 1 d . . . . .
H12C H 0.578611 0.366529 0.738682 0.037 Uiso 1 1 calc R U . . .
H12D H 0.552266 0.518828 0.693103 0.037 Uiso 1 1 calc R U . . .
C13A C 0.4000(2) 0.3421(3) 0.67551(10) 0.0274(5) Uani 1 1 d . . . . .
H13C H 0.328857 0.380620 0.708756 0.033 Uiso 1 1 calc R U . . .
H13D H 0.399727 0.225497 0.676978 0.033 Uiso 1 1 calc R U . . .
C14A C 0.4247(2) 0.3566(2) 0.48460(10) 0.0202(4) Uani 1 1 d . . . . .
C15A C 0.3043(2) 0.2659(3) 0.46545(10) 0.0234(4) Uani 1 1 d . . . . .
H15A H 0.248861 0.213177 0.498520 0.028 Uiso 1 1 calc R U . . .
C16A C 0.2632(2) 0.2506(3) 0.39942(11) 0.0264(4) Uani 1 1 d . . . . .
H16A H 0.181884 0.186462 0.387558 0.032 Uiso 1 1 calc R U . . .
C17A C 0.3412(2) 0.3293(3) 0.35088(11) 0.0277(5) Uani 1 1 d . . . . .
H17A H 0.313073 0.320236 0.305578 0.033 Uiso 1 1 calc R U . . .
C18A C 0.4605(3) 0.4211(3) 0.36868(10) 0.0277(5) Uani 1 1 d . . . . .
H18A H 0.514131 0.475246 0.335420 0.033 Uiso 1 1 calc R U . . .
C19A C 0.5023(2) 0.4348(3) 0.43487(10) 0.0238(4) Uani 1 1 d . . . . .
H19A H 0.584506 0.497982 0.446404 0.029 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.03(10) . . ?
O2 S1 C7 110.79(9) . . ?
O1 S1 C7 108.10(10) . . ?
O2 S1 C2 106.88(10) . . ?
O1 S1 C2 108.54(10) . . ?
C7 S1 C2 103.52(9) . . ?
C2 N1 C6 116.03(19) . . ?
N1 C2 C3 125.8(2) . . ?
N1 C2 S1 114.47(16) . . ?
C3 C2 S1 119.66(17) . . ?
C2 C3 C4 116.9(2) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 123.2(2) . . ?
N1 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C8 C7 S1 112.12(14) . . ?
C8 C7 H7A 109.2 . . ?
S1 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
S1 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C13 112.13(16) . . ?
C9 C8 C7 108.53(16) . . ?
C13 C8 C7 112.10(16) . . ?
C9 C8 H8 108.0 . . ?
C13 C8 H8 108.0 . . ?
C7 C8 H8 108.0 . . ?
C10 C9 C14 120.52(17) . . ?
C10 C9 C8 122.08(17) . . ?
C14 C9 C8 117.39(16) . . ?
C9 C10 C11 124.76(18) . . ?
C9 C10 H10 117.6 . . ?
C11 C10 H10 117.6 . . ?
C10 C11 C12 111.03(17) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 109.97(18) . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C8 111.83(16) . . ?
C12 C13 H13A 109.2 . . ?
C8 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C8 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C19 C14 C15 118.29(19) . . ?
C19 C14 C9 119.69(19) . . ?
C15 C14 C9 122.02(19) . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.9(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
O2A S1A O1A 117.93(11) . . ?
O2A S1A C7A 110.71(10) . . ?
O1A S1A C7A 108.31(10) . . ?
O2A S1A C2A 106.38(10) . . ?
O1A S1A C2A 107.75(10) . . ?
C7A S1A C2A 104.94(10) . . ?
C2A N1A C6A 115.74(18) . . ?
N1A C2A C3A 125.73(19) . . ?
N1A C2A S1A 115.10(15) . . ?
C3A C2A S1A 118.99(16) . . ?
C2A C3A C4A 117.38(19) . . ?
C2A C3A H3A 121.3 . . ?
C4A C3A H3A 121.3 . . ?
C5A C4A C3A 118.5(2) . . ?
C5A C4A H4A 120.7 . . ?
C3A C4A H4A 120.7 . . ?
C4A C5A C6A 119.3(2) . . ?
C4A C5A H5A 120.4 . . ?
C6A C5A H5A 120.4 . . ?
N1A C6A C5A 123.37(19) . . ?
N1A C6A H6A 118.3 . . ?
C5A C6A H6A 118.3 . . ?
C8A C7A S1A 112.29(14) . . ?
C8A C7A H7AA 109.1 . . ?
S1A C7A H7AA 109.1 . . ?
C8A C7A H7AB 109.1 . . ?
S1A C7A H7AB 109.1 . . ?
H7AA C7A H7AB 107.9 . . ?
C9A C8A C13A 111.13(17) . . ?
C9A C8A C7A 106.81(17) . . ?
C13A C8A C7A 114.19(18) . . ?
C9A C8A H8A 108.2 . . ?
C13A C8A H8A 108.2 . . ?
C7A C8A H8A 108.2 . . ?
C10A C9A C14A 121.57(18) . . ?
C10A C9A C8A 121.20(19) . . ?
C14A C9A C8A 117.20(17) . . ?
C9A C10A C11A 125.40(19) . . ?
C9A C10A H10A 117.3 . . ?
C11A C10A H10A 117.3 . . ?
C10A C11A C12A 112.56(18) . . ?
C10A C11A H11C 109.1 . . ?
C12A C11A H11C 109.1 . . ?
C10A C11A H11D 109.1 . . ?
C12A C11A H11D 109.1 . . ?
H11C C11A H11D 107.8 . . ?
C13A C12A C11A 110.65(18) . . ?
C13A C12A H12C 109.5 . . ?
C11A C12A H12C 109.5 . . ?
C13A C12A H12D 109.5 . . ?
C11A C12A H12D 109.5 . . ?
H12C C12A H12D 108.1 . . ?
C12A C13A C8A 111.78(17) . . ?
C12A C13A H13C 109.3 . . ?
C8A C13A H13C 109.3 . . ?
C12A C13A H13D 109.3 . . ?
C8A C13A H13D 109.3 . . ?
H13C C13A H13D 107.9 . . ?
C15A C14A C19A 117.69(19) . . ?
C15A C14A C9A 120.82(17) . . ?
C19A C14A C9A 121.46(18) . . ?
C16A C15A C14A 121.72(19) . . ?
C16A C15A H15A 119.1 . . ?
C14A C15A H15A 119.1 . . ?
C17A C16A C15A 119.7(2) . . ?
C17A C16A H16A 120.1 . . ?
C15A C16A H16A 120.1 . . ?
C16A C17A C18A 119.63(19) . . ?
C16A C17A H17A 120.2 . . ?
C18A C17A H17A 120.2 . . ?
C17A C18A C19A 120.48(19) . . ?
C17A C18A H18A 119.8 . . ?
C19A C18A H18A 119.8 . . ?
C18A C19A C14A 120.7(2) . . ?
C18A C19A H19A 119.6 . . ?
C14A C19A H19A 119.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4385(14) . ?
S1 O1 1.4401(16) . ?
S1 C7 1.7832(19) . ?
S1 C2 1.795(2) . ?
N1 C2 1.337(3) . ?
N1 C6 1.338(3) . ?
C2 C3 1.377(3) . ?
C3 C4 1.395(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.543(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.526(3) . ?
C8 C13 1.540(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.334(3) . ?
C9 C14 1.491(3) . ?
C10 C11 1.504(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.524(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.526(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.396(3) . ?
C14 C15 1.398(3) . ?
C15 C16 1.392(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S1A O2A 1.4382(15) . ?
S1A O1A 1.4414(17) . ?
S1A C7A 1.782(2) . ?
S1A C2A 1.796(2) . ?
N1A C2A 1.334(3) . ?
N1A C6A 1.342(3) . ?
C2A C3A 1.380(3) . ?
C3A C4A 1.392(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.382(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.388(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.545(3) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C9A 1.524(3) . ?
C8A C13A 1.528(3) . ?
C8A H8A 1.0000 . ?
C9A C10A 1.333(3) . ?
C9A C14A 1.487(3) . ?
C10A C11A 1.502(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.532(3) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A C13A 1.520(3) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C14A C15A 1.394(3) . ?
C14A C19A 1.397(3) . ?
C15A C16A 1.386(3) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.384(3) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.384(3) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.390(3) . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 0.4(3) . . . . ?
C6 N1 C2 S1 178.46(15) . . . . ?
O2 S1 C2 N1 -178.16(14) . . . . ?
O1 S1 C2 N1 -49.87(17) . . . . ?
C7 S1 C2 N1 64.81(17) . . . . ?
O2 S1 C2 C3 0.0(2) . . . . ?
O1 S1 C2 C3 128.30(18) . . . . ?
C7 S1 C2 C3 -117.02(18) . . . . ?
N1 C2 C3 C4 -0.4(3) . . . . ?
S1 C2 C3 C4 -178.35(17) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C2 N1 C6 C5 -0.2(3) . . . . ?
C4 C5 C6 N1 -0.1(3) . . . . ?
O2 S1 C7 C8 70.16(16) . . . . ?
O1 S1 C7 C8 -60.59(16) . . . . ?
C2 S1 C7 C8 -175.59(14) . . . . ?
S1 C7 C8 C9 157.65(13) . . . . ?
S1 C7 C8 C13 -77.95(18) . . . . ?
C13 C8 C9 C10 -7.5(3) . . . . ?
C7 C8 C9 C10 116.8(2) . . . . ?
C13 C8 C9 C14 171.83(18) . . . . ?
C7 C8 C9 C14 -63.8(2) . . . . ?
C14 C9 C10 C11 176.2(2) . . . . ?
C8 C9 C10 C11 -4.5(3) . . . . ?
C9 C10 C11 C12 -16.6(3) . . . . ?
C10 C11 C12 C13 48.4(2) . . . . ?
C11 C12 C13 C8 -61.9(2) . . . . ?
C9 C8 C13 C12 40.2(2) . . . . ?
C7 C8 C13 C12 -82.1(2) . . . . ?
C10 C9 C14 C19 -42.4(3) . . . . ?
C8 C9 C14 C19 138.2(2) . . . . ?
C10 C9 C14 C15 137.2(2) . . . . ?
C8 C9 C14 C15 -42.2(3) . . . . ?
C19 C14 C15 C16 1.1(3) . . . . ?
C9 C14 C15 C16 -178.5(2) . . . . ?
C14 C15 C16 C17 -1.9(4) . . . . ?
C15 C16 C17 C18 1.8(4) . . . . ?
C16 C17 C18 C19 -1.0(4) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?
C15 C14 C19 C18 -0.3(3) . . . . ?
C9 C14 C19 C18 179.4(2) . . . . ?
C6A N1A C2A C3A -0.1(3) . . . . ?
C6A N1A C2A S1A 174.88(15) . . . . ?
O2A S1A C2A N1A 169.25(15) . . . . ?
O1A S1A C2A N1A -63.40(17) . . . . ?
C7A S1A C2A N1A 51.86(17) . . . . ?
O2A S1A C2A C3A -15.40(19) . . . . ?
O1A S1A C2A C3A 111.95(17) . . . . ?
C7A S1A C2A C3A -132.79(17) . . . . ?
N1A C2A C3A C4A 1.3(3) . . . . ?
S1A C2A C3A C4A -173.54(16) . . . . ?
C2A C3A C4A C5A -1.2(3) . . . . ?
C3A C4A C5A C6A 0.1(3) . . . . ?
C2A N1A C6A C5A -1.1(3) . . . . ?
C4A C5A C6A N1A 1.1(3) . . . . ?
O2A S1A C7A C8A 80.03(17) . . . . ?
O1A S1A C7A C8A -50.71(17) . . . . ?
C2A S1A C7A C8A -165.58(14) . . . . ?
S1A C7A C8A C9A 172.72(13) . . . . ?
S1A C7A C8A C13A -64.0(2) . . . . ?
C13A C8A C9A C10A -19.8(3) . . . . ?
C7A C8A C9A C10A 105.4(2) . . . . ?
C13A C8A C9A C14A 158.49(18) . . . . ?
C7A C8A C9A C14A -76.4(2) . . . . ?
C14A C9A C10A C11A -177.0(2) . . . . ?
C8A C9A C10A C11A 1.1(3) . . . . ?
C9A C10A C11A C12A -11.5(3) . . . . ?
C10A C11A C12A C13A 40.0(3) . . . . ?
C11A C12A C13A C8A -60.4(2) . . . . ?
C9A C8A C13A C12A 49.1(2) . . . . ?
C7A C8A C13A C12A -71.8(2) . . . . ?
C10A C9A C14A C15A 130.4(2) . . . . ?
C8A C9A C14A C15A -47.8(3) . . . . ?
C10A C9A C14A C19A -47.7(3) . . . . ?
C8A C9A C14A C19A 134.1(2) . . . . ?
C19A C14A C15A C16A 1.1(3) . . . . ?
C9A C14A C15A C16A -177.07(19) . . . . ?
C14A C15A C16A C17A -1.3(3) . . . . ?
C15A C16A C17A C18A 0.7(3) . . . . ?
C16A C17A C18A C19A 0.0(3) . . . . ?
C17A C18A C19A C14A -0.2(3) . . . . ?
C15A C14A C19A C18A -0.4(3) . . . . ?
C9A C14A C19A C18A 177.78(19) . . . . ?
