#------------------------------------------------------------------------------
#$Date: 2022-04-14 01:14:49 +0300 (Thu, 14 Apr 2022) $
#$Revision: 274513 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/67/1566793.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_1566793
loop_
_publ_author_name
'Yan, Qiaolin'
'Duan, Meng'
'Chen, Cien'
'Deng, Zhiqin'
'Wu, Mandi'
'Yu, Peiyuan'
'He, Ming-Liang'
'Zhu, Guangyu'
'Houk, Kendall N.'
'Sun, Jianwei'
_publ_section_title
;
 Organocatalytic Discrimination of Non-Directing Aryl and Heteroaryl
 Groups: Enantioselective Synthesis of Bioactive Indole-Containing
 Triarylmethanes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00636G
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H17 N S'
_chemical_formula_sum            'C20 H17 N S'
_chemical_formula_weight         303.40
_chemical_name_systematic
(S)-3-Methyl-2-(phenyl(thiophen-3-yl)methyl)-1H-indole
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-15
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2021-10-20 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                103.482(4)
_cell_angle_beta                 103.756(4)
_cell_angle_gamma                102.858(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4366(4)
_cell_length_b                   8.5299(4)
_cell_length_c                   11.8199(6)
_cell_measurement_reflns_used    4268
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.1110
_cell_measurement_theta_min      4.0170
_cell_volume                     767.86(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1788
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    120.00 170.00   1.00    2.50    --  113.00  77.00  60.00   50
  2  ω     10.00 105.00   1.00    1.00    --   39.95  57.00 -60.00   95
  3  ω     -7.00  64.00   1.00    1.00    --   39.95 -37.00  30.00   71
  4  ω     12.00  74.00   1.00    1.00    --   39.95 -77.00 -30.00   62
  5  ω     19.00 103.00   1.00    1.00    --   39.95  37.00-150.00   84
  6  ω    -34.00  -8.00   1.00    1.00    --   39.95 -37.00  30.00   26
  7  ω     68.00 109.00   1.00    2.50    --  113.00-111.00-120.00   41
  8  ω     34.00  91.00   1.00    2.50    --  113.00 -77.00 150.00   57
  9  ω     36.00  66.00   1.00    2.50    --  113.00-111.00-120.00   30
 10  ω     88.00 178.00   1.00    2.50    --  113.00  45.00  30.00   90
 11  ω     38.00 109.00   1.00    2.50    --  113.00-111.00  60.00   71
 12  ω     51.00 107.00   1.00    2.50    --  113.00 -94.00  90.00   56
 13  ω     38.00 146.00   1.00    2.50    --  113.00 -77.00-120.00  108
 14  ω     86.00 178.00   1.00    2.50    --  113.00  45.00 -30.00   92
 15  ω     38.00 138.00   1.00    2.50    --  113.00 -30.00   0.00  100
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1082845000
_diffrn_orient_matrix_UB_12      -0.0200404000
_diffrn_orient_matrix_UB_13      0.1176353000
_diffrn_orient_matrix_UB_21      0.1126399000
_diffrn_orient_matrix_UB_22      0.1835208000
_diffrn_orient_matrix_UB_23      0.0350928000
_diffrn_orient_matrix_UB_31      -0.1194999000
_diffrn_orient_matrix_UB_32      0.0606891000
_diffrn_orient_matrix_UB_33      0.0688781000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4569
_diffrn_reflns_point_group_measured_fraction_full 0.546
_diffrn_reflns_point_group_measured_fraction_max 0.528
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.202
_diffrn_reflns_theta_min         4.039
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.811
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.016(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         3400
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0367
_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)+(0.0636P)²+0.3778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.119
_reflns_Friedel_fraction_full    0.123
_reflns_Friedel_fraction_max     0.112
_reflns_number_gt                3388
_reflns_number_total             3400
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00636g2.cif
_cod_data_source_block           qyan2cult
_cod_original_cell_volume        767.85(7)
_cod_database_code               1566793
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H18 O4'
_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_max   0.773
_shelx_estimated_absorpt_t_min   0.531
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-C6 \\sim C9-C7 \\sim C7-C8
 with sigma of 0.02
 C5-C4 \\sim C4-C3 \\sim C3-C2
 with sigma of 0.02
 S2-C6 \\sim S2-C8
 with sigma of 0.02
 S1-C5 \\sim S1-C2
 with sigma of 0.02
 C9-C1 \\sim C3-C1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(S1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of
0.005
Uanis(S2) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C7) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of
0.005
4. Rigid body (RIGU) restrains
 S2, C6, C7, C8, C9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 S1, C2, C3, C4, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: S1(0.77) S2(0.23) H1A(0.77) H1B(0.23) C2(0.77) H2(0.77) C3(0.77)
 C4(0.77) H4(0.77) C5(0.77) H5(0.77) C6(0.23) H6(0.23) C7(0.23) H7(0.23)
 C8(0.23) H8(0.23) C9(0.23)
6.a Ternary CH refined with riding coordinates:
 C1(H1A), C1(H1B), C1A(H1AB)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15),
 C16(H16), C17(H17), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
 N1A(H1AA), C2A(H2A), C4A(H4A), C5A(H5A), C14A(H14A), C15A(H15A), C16A(H16A),
 C17A(H17A), C22A(H22A), C23A(H23A), C24A(H24A), C25A(H25A), C26A(H26A)
6.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C19A(H19D,H19E,H19F)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.686
_oxdiff_exptl_absorpt_empirical_full_min 0.458
loop_
_space_group_symop_operation_xyz
'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 0.32051(16) 0.31294(15) 0.37053(9) 0.0184(3) Uani 0.77 1 d D U P A 1
S2 S 0.2837(8) 0.4550(8) 0.4881(5) 0.0178(12) Uani 0.23 1 d D U P A 2
N1 N 0.7275(3) 0.5330(3) 0.8740(2) 0.0130(5) Uani 1 1 d . . . . .
H1 H 0.6409 0.4772 0.8922 0.016 Uiso 1 1 calc R U . . .
C1 C 0.6715(3) 0.3159(3) 0.6709(2) 0.0111(5) Uani 1 1 d D . . . .
H1A H 0.7521 0.2823 0.6269 0.013 Uiso 0.77 1 calc R U P B 1
H1B H 0.7500 0.2825 0.6247 0.013 Uiso 0.23 1 calc R U P C 2
C2 C 0.4898(9) 0.2672(11) 0.4531(6) 0.0190(14) Uani 0.77 1 d D U P A 1
H2 H 0.5502 0.1981 0.4176 0.023 Uiso 0.77 1 calc R U P A 1
C3 C 0.529(2) 0.341(2) 0.5765(9) 0.0113(10) Uani 0.77 1 d D U P A 1
C4 C 0.427(2) 0.448(3) 0.6030(9) 0.0165(12) Uani 0.77 1 d D U P A 1
H4 H 0.4420 0.5163 0.6830 0.020 Uiso 0.77 1 calc R U P A 1
C5 C 0.3055(11) 0.4422(11) 0.5015(7) 0.0194(14) Uani 0.77 1 d D U P A 1
H5 H 0.2229 0.5018 0.5027 0.023 Uiso 0.77 1 calc R U P A 1
C6 C 0.426(8) 0.449(10) 0.610(3) 0.019(3) Uani 0.23 1 d D U P A 2
H6 H 0.4388 0.5101 0.6916 0.023 Uiso 0.23 1 calc R U P A 2
C7 C 0.465(3) 0.249(4) 0.458(2) 0.018(3) Uani 0.23 1 d D U P A 2
H7 H 0.5026 0.1581 0.4208 0.021 Uiso 0.23 1 calc R U P A 2
C8 C 0.341(3) 0.310(3) 0.3997(19) 0.019(2) Uani 0.23 1 d D U P A 2
H8 H 0.2913 0.2715 0.3134 0.023 Uiso 0.23 1 calc R U P A 2
C9 C 0.526(8) 0.344(9) 0.581(3) 0.018(3) Uani 0.23 1 d D U P A 2
C11 C 0.7724(3) 0.4794(3) 0.7692(2) 0.0117(5) Uani 1 1 d . . . . .
C12 C 0.9109(3) 0.5999(3) 0.7699(3) 0.0127(5) Uani 1 1 d . . . . .
C13 C 0.9547(3) 0.7361(3) 0.8808(3) 0.0124(5) Uani 1 1 d . . . . .
C14 C 1.0847(4) 0.8905(3) 0.9340(3) 0.0154(5) Uani 1 1 d . . . . .
H14 H 1.1635 0.9252 0.8926 0.019 Uiso 1 1 calc R U . . .
C15 C 1.0961(4) 0.9913(4) 1.0479(3) 0.0184(6) Uani 1 1 d . . . . .
H15 H 1.1812 1.0976 1.0835 0.022 Uiso 1 1 calc R U . . .
C16 C 0.9837(4) 0.9386(4) 1.1115(3) 0.0176(6) Uani 1 1 d . . . . .
H16 H 0.9965 1.0084 1.1904 0.021 Uiso 1 1 calc R U . . .
C17 C 0.8537(4) 0.7860(4) 1.0612(3) 0.0153(5) Uani 1 1 d . . . . .
H17 H 0.7775 0.7505 1.1041 0.018 Uiso 1 1 calc R U . . .
C18 C 0.8407(3) 0.6880(3) 0.9452(3) 0.0127(5) Uani 1 1 d . . . . .
C19 C 1.0041(4) 0.5892(4) 0.6764(3) 0.0171(6) Uani 1 1 d . . . . .
H19A H 1.0053 0.6851 0.6440 0.026 Uiso 1 1 calc R U . . .
H19B H 0.9462 0.4838 0.6096 0.026 Uiso 1 1 calc R U . . .
H19C H 1.1216 0.5916 0.7144 0.026 Uiso 1 1 calc R U . . .
C21 C 0.6099(3) 0.1711(3) 0.7213(2) 0.0113(5) Uani 1 1 d . . . . .
C22 C 0.4543(4) 0.0468(3) 0.6594(3) 0.0151(5) Uani 1 1 d . . . . .
H22 H 0.3813 0.0547 0.5874 0.018 Uiso 1 1 calc R U . . .
C23 C 0.4056(4) -0.0900(4) 0.7035(3) 0.0216(6) Uani 1 1 d . . . . .
H23 H 0.2996 -0.1745 0.6609 0.026 Uiso 1 1 calc R U . . .
C24 C 0.5092(4) -0.1024(4) 0.8069(3) 0.0214(6) Uani 1 1 d . . . . .
H24 H 0.4743 -0.1943 0.8369 0.026 Uiso 1 1 calc R U . . .
C25 C 0.6668(4) 0.0203(4) 0.8687(3) 0.0180(6) Uani 1 1 d . . . . .
H25 H 0.7401 0.0109 0.9398 0.022 Uiso 1 1 calc R U . . .
C26 C 0.7156(4) 0.1558(4) 0.8256(3) 0.0155(5) Uani 1 1 d . . . . .
H26 H 0.8225 0.2390 0.8678 0.019 Uiso 1 1 calc R U . . .
S1A S -0.09803(9) 0.46557(10) 0.28459(7) 0.02427(19) Uani 1 1 d . . . . .
N1A N 0.5160(3) 0.7607(3) 0.3929(2) 0.0133(5) Uani 1 1 d . . . . .
H1AA H 0.4550 0.6815 0.4146 0.016 Uiso 1 1 calc R U . . .
C1A C 0.3006(3) 0.6945(3) 0.1872(2) 0.0127(5) Uani 1 1 d . . . . .
H1AB H 0.2635 0.7711 0.1409 0.015 Uiso 1 1 calc R U . . .
C2A C 0.0506(4) 0.4761(4) 0.2061(3) 0.0173(6) Uani 1 1 d . . . . .
H2A H 0.0561 0.3831 0.1463 0.021 Uiso 1 1 calc R U . . .
C3A C 0.1595(3) 0.6364(4) 0.2414(3) 0.0129(5) Uani 1 1 d . . . . .
C4A C 0.1200(4) 0.7494(4) 0.3330(3) 0.0163(5) Uani 1 1 d . . . . .
H4A H 0.1824 0.8655 0.3682 0.020 Uiso 1 1 calc R U . . .
C5A C -0.0166(4) 0.6745(4) 0.3654(3) 0.0203(6) Uani 1 1 d . . . . .
H5A H -0.0600 0.7311 0.4248 0.024 Uiso 1 1 calc R U . . .
C11A C 0.4660(3) 0.7984(3) 0.2849(2) 0.0119(5) Uani 1 1 d . . . . .
C12A C 0.5909(4) 0.9273(3) 0.2813(3) 0.0127(5) Uani 1 1 d . . . . .
C13A C 0.7283(4) 0.9732(3) 0.3920(3) 0.0119(5) Uani 1 1 d . . . . .
C14A C 0.8911(4) 1.0918(4) 0.4409(3) 0.0158(6) Uani 1 1 d . . . . .
H14A H 0.9297 1.1639 0.3965 0.019 Uiso 1 1 calc R U . . .
C15A C 0.9943(4) 1.1027(3) 0.5536(3) 0.0170(6) Uani 1 1 d . . . . .
H15A H 1.1048 1.1821 0.5863 0.020 Uiso 1 1 calc R U . . .
C16A C 0.9379(4) 0.9972(4) 0.6211(3) 0.0159(5) Uani 1 1 d . . . . .
H16A H 1.0108 1.0077 0.6991 0.019 Uiso 1 1 calc R U . . .
C17A C 0.7782(4) 0.8786(4) 0.5757(3) 0.0154(5) Uani 1 1 d . . . . .
H17A H 0.7399 0.8082 0.6212 0.019 Uiso 1 1 calc R U . . .
C18A C 0.6766(3) 0.8667(3) 0.4613(3) 0.0122(5) Uani 1 1 d . . . . .
C19A C 0.5835(4) 1.0106(4) 0.1816(3) 0.0170(6) Uani 1 1 d . . . . .
H19D H 0.5662 1.1212 0.2097 0.025 Uiso 1 1 calc R U . . .
H19E H 0.4886 0.9398 0.1089 0.025 Uiso 1 1 calc R U . . .
H19F H 0.6910 1.0249 0.1615 0.025 Uiso 1 1 calc R U . . .
C21A C 0.3240(3) 0.5505(3) 0.0954(3) 0.0127(5) Uani 1 1 d . . . . .
C22A C 0.4557(4) 0.4792(4) 0.1248(3) 0.0149(5) Uani 1 1 d . . . . .
H22A H 0.5348 0.5204 0.2047 0.018 Uiso 1 1 calc R U . . .
C23A C 0.4718(4) 0.3465(4) 0.0366(3) 0.0185(6) Uani 1 1 d . . . . .
H23A H 0.5611 0.2974 0.0572 0.022 Uiso 1 1 calc R U . . .
C24A C 0.3585(4) 0.2876(4) -0.0796(3) 0.0218(6) Uani 1 1 d . . . . .
H24A H 0.3702 0.1984 -0.1393 0.026 Uiso 1 1 calc R U . . .
C25A C 0.2289(4) 0.3569(4) -0.1094(3) 0.0252(7) Uani 1 1 d . . . . .
H25A H 0.1506 0.3154 -0.1897 0.030 Uiso 1 1 calc R U . . .
C26A C 0.2113(4) 0.4883(4) -0.0225(3) 0.0210(6) Uani 1 1 d . . . . .
H26A H 0.1212 0.5359 -0.0442 0.025 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'
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
C2 S1 C5 91.3(4) . . ?
C8 S2 C6 90(2) . . ?
C11 N1 H1 125.5 . . ?
C18 N1 H1 125.5 . . ?
C18 N1 C11 109.0(2) . . ?
C3 C1 H1A 106.1 . . ?
C3 C1 C21 113.5(9) . . ?
C9 C1 H1B 106.9 . . ?
C9 C1 C21 113(4) . . ?
C11 C1 H1A 106.1 . . ?
C11 C1 H1B 106.9 . . ?
C11 C1 C3 111.0(6) . . ?
C11 C1 C9 110(2) . . ?
C11 C1 C21 113.3(2) . . ?
C21 C1 H1A 106.1 . . ?
C21 C1 H1B 106.9 . . ?
S1 C2 H2 123.8 . . ?
C3 C2 S1 112.5(5) . . ?
C3 C2 H2 123.8 . . ?
C2 C3 C1 123.0(8) . . ?
C2 C3 C4 111.7(6) . . ?
C4 C3 C1 125.2(7) . . ?
C3 C4 H4 123.6 . . ?
C5 C4 C3 112.8(8) . . ?
C5 C4 H4 123.6 . . ?
S1 C5 H5 124.3 . . ?
C4 C5 S1 111.5(8) . . ?
C4 C5 H5 124.3 . . ?
S2 C6 H6 123.5 . . ?
C9 C6 S2 113(2) . . ?
C9 C6 H6 123.5 . . ?
C8 C7 H7 126.3 . . ?
C8 C7 C9 107(2) . . ?
C9 C7 H7 126.3 . . ?
S2 C8 H8 121.6 . . ?
C7 C8 S2 116.7(17) . . ?
C7 C8 H8 121.6 . . ?
C6 C9 C1 126(2) . . ?
C7 C9 C1 122(3) . . ?
C7 C9 C6 112(2) . . ?
N1 C11 C1 122.2(2) . . ?
C12 C11 N1 109.6(2) . . ?
C12 C11 C1 128.1(3) . . ?
C11 C12 C13 106.8(2) . . ?
C11 C12 C19 126.8(3) . . ?
C13 C12 C19 126.4(2) . . ?
C14 C13 C12 133.7(3) . . ?
C14 C13 C18 119.0(3) . . ?
C18 C13 C12 107.2(2) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.9(3) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 120.9(3) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.5(3) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 121.5 . . ?
C16 C17 C18 117.0(3) . . ?
C18 C17 H17 121.5 . . ?
N1 C18 C13 107.5(2) . . ?
N1 C18 C17 129.9(3) . . ?
C17 C18 C13 122.6(3) . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C21 C1 121.1(2) . . ?
C26 C21 C1 119.8(2) . . ?
C26 C21 C22 118.9(2) . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.6(3) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 119.9(3) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.8(3) . . ?
C26 C25 H25 120.1 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.8(3) . . ?
C25 C26 H26 119.6 . . ?
C5A S1A C2A 92.78(15) . . ?
C11A N1A H1AA 125.5 . . ?
C18A N1A H1AA 125.5 . . ?
C18A N1A C11A 109.1(2) . . ?
C3A C1A H1AB 106.4 . . ?
C11A C1A H1AB 106.4 . . ?
C11A C1A C3A 111.9(2) . . ?
C11A C1A C21A 112.1(2) . . ?
C21A C1A H1AB 106.4 . . ?
C21A C1A C3A 112.9(2) . . ?
S1A C2A H2A 124.4 . . ?
C3A C2A S1A 111.1(2) . . ?
C3A C2A H2A 124.4 . . ?
C2A C3A C1A 125.7(3) . . ?
C2A C3A C4A 111.7(3) . . ?
C4A C3A C1A 122.5(2) . . ?
C3A C4A H4A 123.2 . . ?
C5A C4A C3A 113.6(3) . . ?
C5A C4A H4A 123.2 . . ?
S1A C5A H5A 124.6 . . ?
C4A C5A S1A 110.8(2) . . ?
C4A C5A H5A 124.6 . . ?
N1A C11A C1A 121.1(2) . . ?
C12A C11A N1A 109.9(2) . . ?
C12A C11A C1A 128.8(3) . . ?
C11A C12A C13A 107.2(2) . . ?
C11A C12A C19A 126.5(3) . . ?
C13A C12A C19A 126.3(3) . . ?
C14A C13A C12A 134.8(3) . . ?
C14A C13A C18A 118.2(3) . . ?
C18A C13A C12A 107.0(2) . . ?
C13A C14A H14A 120.2 . . ?
C15A C14A C13A 119.6(3) . . ?
C15A C14A H14A 120.2 . . ?
C14A C15A H15A 119.6 . . ?
C14A C15A C16A 120.8(3) . . ?
C16A C15A H15A 119.6 . . ?
C15A C16A H16A 119.4 . . ?
C17A C16A C15A 121.2(3) . . ?
C17A C16A H16A 119.4 . . ?
C16A C17A H17A 121.3 . . ?
C18A C17A C16A 117.5(3) . . ?
C18A C17A H17A 121.3 . . ?
N1A C18A C13A 106.9(2) . . ?
N1A C18A C17A 130.4(2) . . ?
C17A C18A C13A 122.7(2) . . ?
C12A C19A H19D 109.5 . . ?
C12A C19A H19E 109.5 . . ?
C12A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C22A C21A C1A 122.4(2) . . ?
C26A C21A C1A 119.1(3) . . ?
C26A C21A C22A 118.5(3) . . ?
C21A C22A H22A 119.9 . . ?
C21A C22A C23A 120.2(3) . . ?
C23A C22A H22A 119.9 . . ?
C22A C23A H23A 120.0 . . ?
C24A C23A C22A 120.1(3) . . ?
C24A C23A H23A 120.0 . . ?
C23A C24A H24A 119.9 . . ?
C25A C24A C23A 120.2(3) . . ?
C25A C24A H24A 119.9 . . ?
C24A C25A H25A 119.9 . . ?
C24A C25A C26A 120.2(3) . . ?
C26A C25A H25A 119.9 . . ?
C21A C26A C25A 120.8(3) . . ?
C21A C26A H26A 119.6 . . ?
C25A C26A H26A 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 C2 1.705(6) . ?
S1 C5 1.729(8) . ?
S2 C6 1.66(3) . ?
S2 C8 1.66(2) . ?
N1 H1 0.8800 . ?
N1 C11 1.387(4) . ?
N1 C18 1.380(3) . ?
C1 H1A 1.0000 . ?
C1 H1B 1.0000 . ?
C1 C3 1.526(6) . ?
C1 C9 1.526(18) . ?
C1 C11 1.505(4) . ?
C1 C21 1.535(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.373(9) . ?
C3 C4 1.417(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.364(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C9 1.40(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.39(3) . ?
C7 C9 1.39(3) . ?
C8 H8 0.9500 . ?
C11 C12 1.371(4) . ?
C12 C13 1.440(4) . ?
C12 C19 1.499(4) . ?
C13 C14 1.406(4) . ?
C13 C18 1.412(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.405(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C22 1.394(4) . ?
C21 C26 1.392(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.405(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.365(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.400(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.388(4) . ?
C26 H26 0.9500 . ?
S1A C2A 1.727(3) . ?
S1A C5A 1.705(3) . ?
N1A H1AA 0.8800 . ?
N1A C11A 1.382(4) . ?
N1A C18A 1.379(4) . ?
C1A H1AB 1.0000 . ?
C1A C3A 1.523(4) . ?
C1A C11A 1.507(4) . ?
C1A C21A 1.522(4) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.371(4) . ?
C3A C4A 1.429(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.371(4) . ?
C5A H5A 0.9500 . ?
C11A C12A 1.359(4) . ?
C12A C13A 1.430(4) . ?
C12A C19A 1.507(4) . ?
C13A C14A 1.405(4) . ?
C13A C18A 1.424(4) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.376(4) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.414(4) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.387(4) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.385(4) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C21A C22A 1.393(4) . ?
C21A C26A 1.388(4) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.404(4) . ?
C23A H23A 0.9500 . ?
C23A C24A 1.376(5) . ?
C24A H24A 0.9500 . ?
C24A C25A 1.368(5) . ?
C25A H25A 0.9500 . ?
C25A C26A 1.394(5) . ?
C26A H26A 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
S1 C2 C3 C1 177.9(13) . . . . ?
S1 C2 C3 C4 -5(2) . . . . ?
S2 C6 C9 C1 178(6) . . . . ?
S2 C6 C9 C7 -9(9) . . . . ?
N1 C11 C12 C13 -0.1(3) . . . . ?
N1 C11 C12 C19 177.3(3) . . . . ?
C1 C3 C4 C5 -177.8(17) . . . . ?
C1 C11 C12 C13 176.7(3) . . . . ?
C1 C11 C12 C19 -5.8(5) . . . . ?
C1 C21 C22 C23 176.1(3) . . . . ?
C1 C21 C26 C25 -176.1(2) . . . . ?
C2 S1 C5 C4 0.1(14) . . . . ?
C2 C3 C4 C5 5(3) . . . . ?
C3 C1 C11 N1 89.1(9) . . . . ?
C3 C1 C11 C12 -87.4(9) . . . . ?
C3 C1 C21 C22 18.6(6) . . . . ?
C3 C1 C21 C26 -166.2(5) . . . . ?
C3 C4 C5 S1 -3(2) . . . . ?
C5 S1 C2 C3 2.6(12) . . . . ?
C6 S2 C8 C7 2(4) . . . . ?
C8 S2 C6 C9 4(7) . . . . ?
C8 C7 C9 C1 -177(6) . . . . ?
C8 C7 C9 C6 10(8) . . . . ?
C9 C1 C11 N1 87(3) . . . . ?
C9 C1 C11 C12 -90(3) . . . . ?
C9 C1 C21 C22 20.9(17) . . . . ?
C9 C1 C21 C26 -163.8(17) . . . . ?
C9 C7 C8 S2 -7(5) . . . . ?
C11 N1 C18 C13 2.6(3) . . . . ?
C11 N1 C18 C17 -175.5(3) . . . . ?
C11 C1 C3 C2 138.0(15) . . . . ?
C11 C1 C3 C4 -39(2) . . . . ?
C11 C1 C9 C6 -38(9) . . . . ?
C11 C1 C9 C7 149(6) . . . . ?
C11 C1 C21 C22 146.3(3) . . . . ?
C11 C1 C21 C26 -38.5(3) . . . . ?
C11 C12 C13 C14 178.1(3) . . . . ?
C11 C12 C13 C18 1.7(3) . . . . ?
C12 C13 C14 C15 -176.5(3) . . . . ?
C12 C13 C18 N1 -2.7(3) . . . . ?
C12 C13 C18 C17 175.7(3) . . . . ?
C13 C14 C15 C16 2.0(4) . . . . ?
C14 C13 C18 N1 -179.7(2) . . . . ?
C14 C13 C18 C17 -1.4(4) . . . . ?
C14 C15 C16 C17 -1.9(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 N1 179.4(3) . . . . ?
C16 C17 C18 C13 1.5(4) . . . . ?
C18 N1 C11 C1 -178.6(2) . . . . ?
C18 N1 C11 C12 -1.6(3) . . . . ?
C18 C13 C14 C15 -0.4(4) . . . . ?
C19 C12 C13 C14 0.7(5) . . . . ?
C19 C12 C13 C18 -175.8(3) . . . . ?
C21 C1 C3 C2 -93.1(18) . . . . ?
C21 C1 C3 C4 90(2) . . . . ?
C21 C1 C9 C6 89(8) . . . . ?
C21 C1 C9 C7 -84(7) . . . . ?
C21 C1 C11 N1 -39.9(3) . . . . ?
C21 C1 C11 C12 143.6(3) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C22 C21 C26 C25 -0.8(4) . . . . ?
C22 C23 C24 C25 -1.1(5) . . . . ?
C23 C24 C25 C26 1.1(5) . . . . ?
C24 C25 C26 C21 -0.2(4) . . . . ?
C26 C21 C22 C23 0.8(4) . . . . ?
S1A C2A C3A C1A -176.7(2) . . . . ?
S1A C2A C3A C4A 0.1(3) . . . . ?
N1A C11A C12A C13A 0.6(3) . . . . ?
N1A C11A C12A C19A -177.4(2) . . . . ?
C1A C3A C4A C5A 176.9(3) . . . . ?
C1A C11A C12A C13A -174.5(3) . . . . ?
C1A C11A C12A C19A 7.5(5) . . . . ?
C1A C21A C22A C23A -179.9(2) . . . . ?
C1A C21A C26A C25A 179.7(3) . . . . ?
C2A S1A C5A C4A 0.0(2) . . . . ?
C2A C3A C4A C5A -0.1(3) . . . . ?
C3A C1A C11A N1A 36.9(3) . . . . ?
C3A C1A C11A C12A -148.5(3) . . . . ?
C3A C1A C21A C22A -101.7(3) . . . . ?
C3A C1A C21A C26A 78.9(3) . . . . ?
C3A C4A C5A S1A 0.0(3) . . . . ?
C5A S1A C2A C3A -0.1(2) . . . . ?
C11A N1A C18A C13A -0.6(3) . . . . ?
C11A N1A C18A C17A 179.1(3) . . . . ?
C11A C1A C3A C2A -133.6(3) . . . . ?
C11A C1A C3A C4A 49.8(3) . . . . ?
C11A C1A C21A C22A 25.9(4) . . . . ?
C11A C1A C21A C26A -153.5(3) . . . . ?
C11A C12A C13A C14A 178.5(3) . . . . ?
C11A C12A C13A C18A -1.0(3) . . . . ?
C12A C13A C14A C15A -179.9(3) . . . . ?
C12A C13A C18A N1A 0.9(3) . . . . ?
C12A C13A C18A C17A -178.8(3) . . . . ?
C13A C14A C15A C16A -0.6(4) . . . . ?
C14A C13A C18A N1A -178.6(2) . . . . ?
C14A C13A C18A C17A 1.7(4) . . . . ?
C14A C15A C16A C17A 0.7(4) . . . . ?
C15A C16A C17A C18A 0.4(4) . . . . ?
C16A C17A C18A N1A 178.8(3) . . . . ?
C16A C17A C18A C13A -1.6(4) . . . . ?
C18A N1A C11A C1A 175.5(2) . . . . ?
C18A N1A C11A C12A 0.0(3) . . . . ?
C18A C13A C14A C15A -0.5(4) . . . . ?
C19A C12A C13A C14A -3.5(5) . . . . ?
C19A C12A C13A C18A 177.0(3) . . . . ?
C21A C1A C3A C2A -6.0(4) . . . . ?
C21A C1A C3A C4A 177.5(3) . . . . ?
C21A C1A C11A N1A -91.2(3) . . . . ?
C21A C1A C11A C12A 83.4(3) . . . . ?
C21A C22A C23A C24A 0.6(4) . . . . ?
C22A C21A C26A C25A 0.3(4) . . . . ?
C22A C23A C24A C25A -0.5(4) . . . . ?
C23A C24A C25A C26A 0.3(5) . . . . ?
C24A C25A C26A C21A -0.2(5) . . . . ?
C26A C21A C22A C23A -0.5(4) . . . . ?
