#------------------------------------------------------------------------------
#$Date: 2024-04-05 01:54:41 +0200 (Fri 05 de Apr de 2024) $
#$Revision: 291000 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/81/7248181.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_7248181
loop_
_publ_author_name
'Wang, Zhen'
'Gausmann, Marcel'
'Dickoff, Jan-Hendrik'
'Christmann, Mathias'
_publ_section_title
;
 Iodine-enabled organoelectrocatalysis: enantioselective cross
 dehydrogenative coupling of sulfides and aldehydes
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              2546
_journal_page_last               2551
_journal_paper_doi               10.1039/D3GC03828A
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_sum            'C22 H24 N2 O6 S'
_chemical_formula_weight         444.49
_chemical_name_systematic
'(R)-2-cyclohexyl-2-(p-tolylthio)ethyl 3,5-dinitrobenzoate'
_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
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-05-18 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.4062(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.34031(9)
_cell_length_b                   7.13358(5)
_cell_length_c                   24.66536(18)
_cell_measurement_reflns_used    9212
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.65
_cell_volume                     2128.42(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            34981
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.209
_diffrn_reflns_theta_min         3.654
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1634 before and 0.1073 after correction.
The Ratio of minimum to maximum transmission is 0.5908.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       rod
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.4449
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.174
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         7622
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0552
_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)+(0.0774P)²+0.4244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7315
_reflns_number_total             7622
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc03828a2.cif
_cod_data_source_block           ZW_CH119
_cod_depositor_comments          'Adding full bibliography for 7248181.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7248181
_shelx_shelxl_version_number     2019/3
_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   0.431
_shelx_estimated_absorpt_t_max   0.919
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 0.41218(6) 0.23944(12) 0.83206(3) 0.0230(2) Uani 1 1 d . . . . .
O1 O 0.3969(2) 0.6668(3) 0.85353(10) 0.0212(5) Uani 1 1 d . . . . .
O2 O 0.4298(2) 0.7060(4) 0.94650(10) 0.0261(5) Uani 1 1 d . . . . .
O3 O 0.6554(2) 0.8350(5) 0.74410(11) 0.0331(6) Uani 1 1 d . . . . .
O4 O 0.7956(3) 1.0095(6) 0.77726(12) 0.0484(9) Uani 1 1 d . . . . .
O5 O 0.7917(2) 0.9947(4) 1.02756(10) 0.0342(7) Uani 1 1 d . . . . .
O6 O 0.9038(2) 1.0792(5) 0.97487(11) 0.0331(6) Uani 1 1 d . . . . .
N1 N 0.7151(3) 0.9161(5) 0.78200(12) 0.0256(7) Uani 1 1 d . . . . .
N2 N 0.8170(3) 1.0107(4) 0.98198(12) 0.0226(6) Uani 1 1 d . . . . .
C1 C 0.2131(3) 0.2459(5) 0.86731(13) 0.0206(7) Uani 1 1 d . . . . .
H1 H 0.159067 0.331172 0.880273 0.025 Uiso 1 1 calc R U . . .
C2 C 0.2275(3) 0.0766(5) 0.90554(15) 0.0268(8) Uani 1 1 d . . . . .
H2A H 0.258797 0.117515 0.943785 0.032 Uiso 1 1 calc R U . . .
H2B H 0.280153 -0.012273 0.893938 0.032 Uiso 1 1 calc R U . . .
C3 C 0.1173(3) -0.0222(6) 0.90440(17) 0.0302(8) Uani 1 1 d . . . . .
H3A H 0.129788 -0.135900 0.927832 0.036 Uiso 1 1 calc R U . . .
H3B H 0.067382 0.062074 0.919890 0.036 Uiso 1 1 calc R U . . .
C4 C 0.0629(3) -0.0772(6) 0.84585(18) 0.0294(8) Uani 1 1 d . . . . .
H4A H -0.010863 -0.131634 0.846051 0.035 Uiso 1 1 calc R U . . .
H4B H 0.108151 -0.174399 0.832220 0.035 Uiso 1 1 calc R U . . .
C5 C 0.0501(3) 0.0900(6) 0.80700(17) 0.0297(8) Uani 1 1 d . . . . .
H5A H -0.002481 0.180427 0.817969 0.036 Uiso 1 1 calc R U . . .
H5B H 0.019169 0.047501 0.768877 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1608(3) 0.1877(6) 0.80799(15) 0.0270(8) Uani 1 1 d . . . . .
H6A H 0.149137 0.299986 0.783945 0.032 Uiso 1 1 calc R U . . .
H6B H 0.211263 0.101791 0.793489 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3223(3) 0.3568(5) 0.87240(14) 0.0191(7) Uani 1 1 d . . . . .
H7 H 0.360466 0.356761 0.912140 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2975(3) 0.5589(5) 0.85450(15) 0.0217(7) Uani 1 1 d . . . . .
H8A H 0.249957 0.560118 0.817117 0.026 Uiso 1 1 calc R U . . .
H8B H 0.255853 0.619313 0.880205 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4561(3) 0.7241(5) 0.90182(13) 0.0191(7) Uani 1 1 d . . . . .
C10 C 0.5624(3) 0.8114(5) 0.89464(14) 0.0188(7) Uani 1 1 d . . . . .
C11 C 0.5872(3) 0.8248(5) 0.84168(14) 0.0188(7) Uani 1 1 d . . . . .
H11 H 0.536759 0.782538 0.809828 0.023 Uiso 1 1 calc R U . . .
C12 C 0.6887(3) 0.9025(5) 0.83767(14) 0.0206(7) Uani 1 1 d . . . . .
C13 C 0.7652(3) 0.9634(5) 0.88200(15) 0.0199(7) Uani 1 1 d . . . . .
H13 H 0.834036 1.014996 0.877758 0.024 Uiso 1 1 calc R U . . .
C14 C 0.7371(3) 0.9459(5) 0.93360(14) 0.0192(7) Uani 1 1 d . . . . .
C15 C 0.6369(3) 0.8713(5) 0.94053(14) 0.0206(7) Uani 1 1 d . . . . .
H15 H 0.619992 0.861677 0.976355 0.025 Uiso 1 1 calc R U . . .
C16 C 0.5464(3) 0.3222(5) 0.86159(15) 0.0207(7) Uani 1 1 d . . . . .
C17 C 0.5875(3) 0.3360(5) 0.91812(14) 0.0210(7) Uani 1 1 d . . . . .
H17 H 0.541755 0.303007 0.943417 0.025 Uiso 1 1 calc R U . . .
C18 C 0.6943(3) 0.3974(5) 0.93786(16) 0.0254(8) Uani 1 1 d . . . . .
H18 H 0.719864 0.411193 0.976589 0.030 Uiso 1 1 calc R U . . .
C19 C 0.7657(3) 0.4399(5) 0.90163(18) 0.0276(8) Uani 1 1 d . . . . .
C20 C 0.7249(3) 0.4208(5) 0.84510(17) 0.0274(8) Uani 1 1 d . . . . .
H20 H 0.772027 0.445816 0.819829 0.033 Uiso 1 1 calc R U . . .
C21 C 0.6164(3) 0.3657(5) 0.82499(15) 0.0238(7) Uani 1 1 d . . . . .
H21 H 0.589459 0.357487 0.786224 0.029 Uiso 1 1 calc R U . . .
C22 C 0.8835(3) 0.5027(7) 0.9231(2) 0.0400(10) Uani 1 1 d . . . . .
H22A H 0.903964 0.597274 0.898106 0.060 Uiso 1 1 calc R U . . .
H22B H 0.933248 0.394799 0.924968 0.060 Uiso 1 1 calc R U . . .
H22C H 0.889527 0.556726 0.960097 0.060 Uiso 1 1 calc R U . . .
S1B S 0.94549(8) 0.70308(14) 0.35664(3) 0.0289(2) Uani 1 1 d . . . . .
O1B O 0.7972(2) 0.7231(4) 0.48964(9) 0.0271(5) Uani 1 1 d . . . . .
O2B O 0.9745(2) 0.7188(5) 0.53519(10) 0.0327(6) Uani 1 1 d . . . . .
O3B O 1.0522(2) 0.6285(5) 0.73349(11) 0.0370(7) Uani 1 1 d . . . . .
O4B O 0.9246(3) 0.5418(5) 0.77682(12) 0.0442(8) Uani 1 1 d . . . . .
O5B O 0.5104(3) 0.5215(6) 0.58921(14) 0.0519(10) Uani 1 1 d . . . . .
O6B O 0.5562(3) 0.4239(5) 0.67304(14) 0.0446(8) Uani 1 1 d . . . . .
N1B N 0.9567(3) 0.5882(5) 0.73449(13) 0.0291(7) Uani 1 1 d . . . . .
N2B N 0.5785(3) 0.4953(6) 0.63166(14) 0.0348(8) Uani 1 1 d . . . . .
C1B C 0.7672(3) 0.5009(6) 0.38131(14) 0.0247(8) Uani 1 1 d . . . . .
H1B H 0.724137 0.473959 0.410773 0.030 Uiso 1 1 calc R U . . .
C2B C 0.8025(3) 0.3126(6) 0.36155(15) 0.0267(8) Uani 1 1 d . . . . .
H2BA H 0.848514 0.246298 0.393178 0.032 Uiso 1 1 calc R U . . .
H2BB H 0.848553 0.334378 0.333543 0.032 Uiso 1 1 calc R U . . .
C3B C 0.7047(3) 0.1880(6) 0.33646(16) 0.0324(9) Uani 1 1 d . . . . .
H3BA H 0.732382 0.071805 0.321922 0.039 Uiso 1 1 calc R U . . .
H3BB H 0.663631 0.152272 0.365533 0.039 Uiso 1 1 calc R U . . .
C4B C 0.6274(4) 0.2889(6) 0.28998(16) 0.0318(9) Uani 1 1 d . . . . .
H4BA H 0.561928 0.209376 0.276354 0.038 Uiso 1 1 calc R U . . .
H4BB H 0.665784 0.310543 0.258880 0.038 Uiso 1 1 calc R U . . .
C5B C 0.5901(3) 0.4764(6) 0.30989(17) 0.0318(9) Uani 1 1 d . . . . .
H5BA H 0.544841 0.453494 0.338192 0.038 Uiso 1 1 calc R U . . .
H5BB H 0.543229 0.542274 0.278416 0.038 Uiso 1 1 calc R U . . .
C6B C 0.6888(3) 0.6017(6) 0.33462(15) 0.0268(8) Uani 1 1 d . . . . .
H6BA H 0.729442 0.636619 0.305288 0.032 Uiso 1 1 calc R U . . .
H6BB H 0.661581 0.718291 0.349107 0.032 Uiso 1 1 calc R U . . .
C7B C 0.8686(3) 0.6192(6) 0.40851(15) 0.0265(8) Uani 1 1 d . . . . .
H7B H 0.918918 0.537149 0.435188 0.032 Uiso 1 1 calc R U . . .
C8B C 0.8367(4) 0.7876(6) 0.44051(15) 0.0290(8) Uani 1 1 d . . . . .
H8BA H 0.901651 0.870319 0.451843 0.035 Uiso 1 1 calc R U . . .
H8BB H 0.777896 0.860706 0.416453 0.035 Uiso 1 1 calc R U . . .
C9B C 0.8770(3) 0.6997(6) 0.53451(14) 0.0263(8) Uani 1 1 d . . . . .
C10B C 0.8342(3) 0.6479(5) 0.58516(14) 0.0239(8) Uani 1 1 d . . . . .
C11B C 0.9100(3) 0.6440(5) 0.63442(15) 0.0246(8) Uani 1 1 d . . . . .
H11B H 0.985196 0.674749 0.635341 0.029 Uiso 1 1 calc R U . . .
C12B C 0.8751(3) 0.5947(5) 0.68255(14) 0.0240(7) Uani 1 1 d . . . . .
C13B C 0.7670(3) 0.5442(5) 0.68294(15) 0.0266(8) Uani 1 1 d . . . . .
H13B H 0.744396 0.507137 0.715993 0.032 Uiso 1 1 calc R U . . .
C14B C 0.6941(3) 0.5505(6) 0.63302(16) 0.0279(8) Uani 1 1 d . . . . .
C15B C 0.7236(3) 0.6018(6) 0.58360(16) 0.0276(8) Uani 1 1 d . . . . .
H15B H 0.670488 0.605461 0.549971 0.033 Uiso 1 1 calc R U . . .
C16B C 1.0864(3) 0.6551(5) 0.38681(15) 0.0260(8) Uani 1 1 d . . . . .
C17B C 1.1317(3) 0.6710(5) 0.44319(14) 0.0256(8) Uani 1 1 d . . . . .
H17B H 1.086110 0.704774 0.468497 0.031 Uiso 1 1 calc R U . . .
C18B C 1.2439(4) 0.6369(6) 0.46212(15) 0.0297(8) Uani 1 1 d . . . . .
H18B H 1.273718 0.646821 0.500589 0.036 Uiso 1 1 calc R U . . .
C19B C 1.3138(3) 0.5888(6) 0.42645(16) 0.0300(8) Uani 1 1 d . . . . .
C20B C 1.2677(3) 0.5744(6) 0.36992(16) 0.0284(8) Uani 1 1 d . . . . .
H20B H 1.313634 0.542609 0.344606 0.034 Uiso 1 1 calc R U . . .
C21B C 1.1561(3) 0.6060(5) 0.35054(15) 0.0264(8) Uani 1 1 d . . . . .
H21B H 1.126350 0.594254 0.312119 0.032 Uiso 1 1 calc R U . . .
C22B C 1.4347(4) 0.5515(8) 0.44777(19) 0.0415(10) Uani 1 1 d . . . . .
H22D H 1.450806 0.419447 0.441730 0.062 Uiso 1 1 calc R U . . .
H22E H 1.453392 0.579556 0.487415 0.062 Uiso 1 1 calc R U . . .
H22F H 1.478814 0.631176 0.428032 0.062 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
C16 S1 C7 103.97(16) . . ?
C9 O1 C8 117.6(3) . . ?
O3 N1 O4 124.5(3) . . ?
O3 N1 C12 118.2(3) . . ?
O4 N1 C12 117.3(3) . . ?
O6 N2 O5 123.8(3) . . ?
O6 N2 C14 118.5(3) . . ?
O5 N2 C14 117.7(3) . . ?
C2 C1 C6 110.6(3) . . ?
C2 C1 C7 111.3(3) . . ?
C6 C1 C7 114.3(3) . . ?
C2 C1 H1 106.8 . . ?
C6 C1 H1 106.8 . . ?
C7 C1 H1 106.8 . . ?
C1 C2 C3 111.1(3) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 111.2(3) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C5 111.6(3) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 111.6(3) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C1 110.1(3) . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C1 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C1 109.8(3) . . ?
C8 C7 S1 112.6(2) . . ?
C1 C7 S1 109.5(2) . . ?
C8 C7 H7 108.3 . . ?
C1 C7 H7 108.3 . . ?
S1 C7 H7 108.3 . . ?
O1 C8 C7 112.6(3) . . ?
O1 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
O1 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O2 C9 O1 125.5(3) . . ?
O2 C9 C10 123.4(3) . . ?
O1 C9 C10 111.1(3) . . ?
C15 C10 C11 120.7(3) . . ?
C15 C10 C9 119.4(3) . . ?
C11 C10 C9 119.8(3) . . ?
C12 C11 C10 117.3(3) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
C13 C12 C11 124.0(3) . . ?
C13 C12 N1 118.6(3) . . ?
C11 C12 N1 117.4(3) . . ?
C12 C13 C14 116.5(3) . . ?
C12 C13 H13 121.8 . . ?
C14 C13 H13 121.8 . . ?
C15 C14 C13 122.5(3) . . ?
C15 C14 N2 119.6(3) . . ?
C13 C14 N2 117.9(3) . . ?
C10 C15 C14 119.0(3) . . ?
C10 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C21 118.8(3) . . ?
C17 C16 S1 124.1(3) . . ?
C21 C16 S1 117.0(3) . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 117.8(3) . . ?
C20 C19 C22 120.8(4) . . ?
C18 C19 C22 121.4(4) . . ?
C21 C20 C19 121.2(4) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C16 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16B S1B C7B 104.01(17) . . ?
C9B O1B C8B 114.3(3) . . ?
O3B N1B O4B 123.7(3) . . ?
O3B N1B C12B 118.4(3) . . ?
O4B N1B C12B 118.0(3) . . ?
O6B N2B O5B 123.4(4) . . ?
O6B N2B C14B 118.0(3) . . ?
O5B N2B C14B 118.5(3) . . ?
C2B C1B C6B 110.6(3) . . ?
C2B C1B C7B 111.2(3) . . ?
C6B C1B C7B 114.0(3) . . ?
C2B C1B H1B 106.9 . . ?
C6B C1B H1B 106.9 . . ?
C7B C1B H1B 106.9 . . ?
C1B C2B C3B 113.0(3) . . ?
C1B C2B H2BA 109.0 . . ?
C3B C2B H2BA 109.0 . . ?
C1B C2B H2BB 109.0 . . ?
C3B C2B H2BB 109.0 . . ?
H2BA C2B H2BB 107.8 . . ?
C4B C3B C2B 110.9(3) . . ?
C4B C3B H3BA 109.5 . . ?
C2B C3B H3BA 109.5 . . ?
C4B C3B H3BB 109.5 . . ?
C2B C3B H3BB 109.5 . . ?
H3BA C3B H3BB 108.0 . . ?
C3B C4B C5B 110.9(3) . . ?
C3B C4B H4BA 109.5 . . ?
C5B C4B H4BA 109.5 . . ?
C3B C4B H4BB 109.5 . . ?
C5B C4B H4BB 109.5 . . ?
H4BA C4B H4BB 108.1 . . ?
C4B C5B C6B 111.8(3) . . ?
C4B C5B H5BA 109.3 . . ?
C6B C5B H5BA 109.3 . . ?
C4B C5B H5BB 109.3 . . ?
C6B C5B H5BB 109.3 . . ?
H5BA C5B H5BB 107.9 . . ?
C1B C6B C5B 111.1(3) . . ?
C1B C6B H6BA 109.4 . . ?
C5B C6B H6BA 109.4 . . ?
C1B C6B H6BB 109.4 . . ?
C5B C6B H6BB 109.4 . . ?
H6BA C6B H6BB 108.0 . . ?
C8B C7B C1B 112.5(3) . . ?
C8B C7B S1B 108.9(3) . . ?
C1B C7B S1B 111.1(2) . . ?
C8B C7B H7B 108.0 . . ?
C1B C7B H7B 108.0 . . ?
S1B C7B H7B 108.0 . . ?
O1B C8B C7B 109.9(3) . . ?
O1B C8B H8BA 109.7 . . ?
C7B C8B H8BA 109.7 . . ?
O1B C8B H8BB 109.7 . . ?
C7B C8B H8BB 109.7 . . ?
H8BA C8B H8BB 108.2 . . ?
O2B C9B O1B 124.4(3) . . ?
O2B C9B C10B 122.1(3) . . ?
O1B C9B C10B 113.4(3) . . ?
C11B C10B C15B 120.5(3) . . ?
C11B C10B C9B 116.8(3) . . ?
C15B C10B C9B 122.7(3) . . ?
C10B C11B C12B 119.3(3) . . ?
C10B C11B H11B 120.4 . . ?
C12B C11B H11B 120.4 . . ?
C13B C12B C11B 122.3(3) . . ?
C13B C12B N1B 118.8(3) . . ?
C11B C12B N1B 118.8(3) . . ?
C14B C13B C12B 116.5(3) . . ?
C14B C13B H13B 121.7 . . ?
C12B C13B H13B 121.7 . . ?
C13B C14B C15B 123.8(4) . . ?
C13B C14B N2B 118.1(3) . . ?
C15B C14B N2B 118.1(3) . . ?
C14B C15B C10B 117.5(4) . . ?
C14B C15B H15B 121.2 . . ?
C10B C15B H15B 121.2 . . ?
C17B C16B C21B 118.7(4) . . ?
C17B C16B S1B 124.4(3) . . ?
C21B C16B S1B 116.9(3) . . ?
C18B C17B C16B 119.7(3) . . ?
C18B C17B H17B 120.2 . . ?
C16B C17B H17B 120.2 . . ?
C19B C18B C17B 122.1(3) . . ?
C19B C18B H18B 119.0 . . ?
C17B C18B H18B 119.0 . . ?
C18B C19B C20B 117.8(4) . . ?
C18B C19B C22B 121.2(4) . . ?
C20B C19B C22B 120.9(4) . . ?
C21B C20B C19B 120.8(4) . . ?
C21B C20B H20B 119.6 . . ?
C19B C20B H20B 119.6 . . ?
C20B C21B C16B 121.0(3) . . ?
C20B C21B H21B 119.5 . . ?
C16B C21B H21B 119.5 . . ?
C19B C22B H22D 109.5 . . ?
C19B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C19B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 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 C16 1.774(4) . ?
S1 C7 1.833(3) . ?
O1 C9 1.332(4) . ?
O1 C8 1.453(4) . ?
O2 C9 1.216(4) . ?
O3 N1 1.216(5) . ?
O4 N1 1.221(5) . ?
O5 N2 1.230(4) . ?
O6 N2 1.221(4) . ?
N1 C12 1.476(4) . ?
N2 C14 1.464(5) . ?
C1 C2 1.521(5) . ?
C1 C6 1.535(5) . ?
C1 C7 1.546(5) . ?
C1 H1 1.0000 . ?
C2 C3 1.527(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.519(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.519(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.529(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(5) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.494(5) . ?
C10 C15 1.378(5) . ?
C10 C11 1.403(4) . ?
C11 C12 1.390(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.367(5) . ?
C13 C14 1.390(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(5) . ?
C16 C21 1.401(5) . ?
C17 C18 1.383(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.407(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(6) . ?
C19 C22 1.513(5) . ?
C20 C21 1.389(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
S1B C16B 1.784(4) . ?
S1B C7B 1.837(4) . ?
O1B C9B 1.339(5) . ?
O1B C8B 1.467(4) . ?
O2B C9B 1.207(5) . ?
O3B N1B 1.218(4) . ?
O4B N1B 1.233(4) . ?
O5B N2B 1.220(5) . ?
O6B N2B 1.220(5) . ?
N1B C12B 1.465(5) . ?
N2B C14B 1.474(5) . ?
C1B C2B 1.522(5) . ?
C1B C6B 1.529(5) . ?
C1B C7B 1.548(6) . ?
C1B H1B 1.0000 . ?
C2B C3B 1.527(6) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C3B C4B 1.520(6) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C4B C5B 1.527(6) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C5B C6B 1.537(6) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C8B 1.531(5) . ?
C7B H7B 1.0000 . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B C10B 1.496(5) . ?
C10B C11B 1.379(5) . ?
C10B C15B 1.398(6) . ?
C11B C12B 1.385(5) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.384(6) . ?
C13B C14B 1.375(6) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.389(5) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.397(5) . ?
C16B C21B 1.403(5) . ?
C17B C18B 1.393(6) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.391(6) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.402(6) . ?
C19B C22B 1.505(6) . ?
C20B C21B 1.384(6) . ?
C20B H20B 0.9500 . ?
C21B H21B 0.9500 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
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 C1 C2 C3 -57.1(4) . . . . ?
C7 C1 C2 C3 174.8(3) . . . . ?
C1 C2 C3 C4 55.7(4) . . . . ?
C2 C3 C4 C5 -54.5(4) . . . . ?
C3 C4 C5 C6 55.2(4) . . . . ?
C4 C5 C6 C1 -56.1(4) . . . . ?
C2 C1 C6 C5 57.0(4) . . . . ?
C7 C1 C6 C5 -176.5(3) . . . . ?
C2 C1 C7 C8 -156.1(3) . . . . ?
C6 C1 C7 C8 77.7(4) . . . . ?
C2 C1 C7 S1 79.7(3) . . . . ?
C6 C1 C7 S1 -46.4(4) . . . . ?
C16 S1 C7 C8 79.0(3) . . . . ?
C16 S1 C7 C1 -158.5(2) . . . . ?
C9 O1 C8 C7 -76.6(4) . . . . ?
C1 C7 C8 O1 -174.8(3) . . . . ?
S1 C7 C8 O1 -52.5(3) . . . . ?
C8 O1 C9 O2 -5.8(5) . . . . ?
C8 O1 C9 C10 172.8(3) . . . . ?
O2 C9 C10 C15 1.6(5) . . . . ?
O1 C9 C10 C15 -177.0(3) . . . . ?
O2 C9 C10 C11 179.1(3) . . . . ?
O1 C9 C10 C11 0.5(4) . . . . ?
C15 C10 C11 C12 -0.7(5) . . . . ?
C9 C10 C11 C12 -178.2(3) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C10 C11 C12 N1 179.8(3) . . . . ?
O3 N1 C12 C13 168.3(4) . . . . ?
O4 N1 C12 C13 -12.0(5) . . . . ?
O3 N1 C12 C11 -10.7(5) . . . . ?
O4 N1 C12 C11 169.0(4) . . . . ?
C11 C12 C13 C14 -0.5(5) . . . . ?
N1 C12 C13 C14 -179.3(3) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C12 C13 C14 N2 -179.7(3) . . . . ?
O6 N2 C14 C15 -178.6(3) . . . . ?
O5 N2 C14 C15 0.5(5) . . . . ?
O6 N2 C14 C13 0.9(5) . . . . ?
O5 N2 C14 C13 -179.9(3) . . . . ?
C11 C10 C15 C14 0.2(5) . . . . ?
C9 C10 C15 C14 177.7(3) . . . . ?
C13 C14 C15 C10 0.3(5) . . . . ?
N2 C14 C15 C10 179.8(3) . . . . ?
C7 S1 C16 C17 44.5(3) . . . . ?
C7 S1 C16 C21 -139.3(3) . . . . ?
C21 C16 C17 C18 2.1(5) . . . . ?
S1 C16 C17 C18 178.3(3) . . . . ?
C16 C17 C18 C19 -2.7(5) . . . . ?
C17 C18 C19 C20 1.0(5) . . . . ?
C17 C18 C19 C22 -178.6(3) . . . . ?
C18 C19 C20 C21 1.4(6) . . . . ?
C22 C19 C20 C21 -179.1(4) . . . . ?
C19 C20 C21 C16 -2.0(6) . . . . ?
C17 C16 C21 C20 0.3(5) . . . . ?
S1 C16 C21 C20 -176.2(3) . . . . ?
C6B C1B C2B C3B -54.5(4) . . . . ?
C7B C1B C2B C3B 177.7(3) . . . . ?
C1B C2B C3B C4B 55.0(4) . . . . ?
C2B C3B C4B C5B -54.8(4) . . . . ?
C3B C4B C5B C6B 55.9(4) . . . . ?
C2B C1B C6B C5B 54.1(4) . . . . ?
C7B C1B C6B C5B -179.7(3) . . . . ?
C4B C5B C6B C1B -55.6(4) . . . . ?
C2B C1B C7B C8B -166.8(3) . . . . ?
C6B C1B C7B C8B 67.3(4) . . . . ?
C2B C1B C7B S1B 70.8(3) . . . . ?
C6B C1B C7B S1B -55.1(4) . . . . ?
C16B S1B C7B C8B 101.7(3) . . . . ?
C16B S1B C7B C1B -133.8(3) . . . . ?
C9B O1B C8B C7B 87.7(4) . . . . ?
C1B C7B C8B O1B 68.7(4) . . . . ?
S1B C7B C8B O1B -167.6(2) . . . . ?
C8B O1B C9B O2B -3.9(5) . . . . ?
C8B O1B C9B C10B 175.6(3) . . . . ?
O2B C9B C10B C11B 7.3(6) . . . . ?
O1B C9B C10B C11B -172.2(3) . . . . ?
O2B C9B C10B C15B -171.5(4) . . . . ?
O1B C9B C10B C15B 8.9(5) . . . . ?
C15B C10B C11B C12B -0.3(6) . . . . ?
C9B C10B C11B C12B -179.2(3) . . . . ?
C10B C11B C12B C13B 1.7(6) . . . . ?
C10B C11B C12B N1B 179.0(3) . . . . ?
O3B N1B C12B C13B 178.2(4) . . . . ?
O4B N1B C12B C13B -1.7(5) . . . . ?
O3B N1B C12B C11B 0.8(5) . . . . ?
O4B N1B C12B C11B -179.1(4) . . . . ?
C11B C12B C13B C14B -1.9(5) . . . . ?
N1B C12B C13B C14B -179.2(3) . . . . ?
C12B C13B C14B C15B 0.7(6) . . . . ?
C12B C13B C14B N2B 179.2(3) . . . . ?
O6B N2B C14B C13B -9.4(6) . . . . ?
O5B N2B C14B C13B 171.4(4) . . . . ?
O6B N2B C14B C15B 169.2(4) . . . . ?
O5B N2B C14B C15B -10.0(6) . . . . ?
C13B C14B C15B C10B 0.6(6) . . . . ?
N2B C14B C15B C10B -178.0(3) . . . . ?
C11B C10B C15B C14B -0.8(6) . . . . ?
C9B C10B C15B C14B 178.1(4) . . . . ?
C7B S1B C16B C17B -36.5(4) . . . . ?
C7B S1B C16B C21B 146.3(3) . . . . ?
C21B C16B C17B C18B -0.4(6) . . . . ?
S1B C16B C17B C18B -177.6(3) . . . . ?
C16B C17B C18B C19B 0.6(6) . . . . ?
C17B C18B C19B C20B -0.2(6) . . . . ?
C17B C18B C19B C22B -179.6(4) . . . . ?
C18B C19B C20B C21B -0.4(6) . . . . ?
C22B C19B C20B C21B 179.0(4) . . . . ?
C19B C20B C21B C16B 0.7(6) . . . . ?
C17B C16B C21B C20B -0.3(6) . . . . ?
S1B C16B C21B C20B 177.1(3) . . . . ?
