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#$Date: 2025-09-20 01:09:48 +0300 (Sat, 20 Sep 2025) $
#$Revision: 302196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/58/1575835.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_1575835
loop_
_publ_author_name
'Head, Joshua'
'Schubert, Tanner'
'Zhao, Biyu'
'Dong, Yuyang'
_publ_section_title
;
 Cu-Catalyzed Enantioconvergent Deborylative Alkynylation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC04733A
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H19 N S'
_chemical_formula_sum            'C20 H19 N S'
_chemical_formula_weight         305.42
_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_date             2025-04-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2025-04-23 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.008(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6964(17)
_cell_length_b                   8.141(3)
_cell_length_c                   17.530(5)
_cell_measurement_reflns_used    2185
_cell_measurement_temperature    118.67
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.76
_cell_volume                     809.8(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      118.67
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10695
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.156
_diffrn_reflns_theta_max         25.156
_diffrn_reflns_theta_min         2.761
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5217
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0885 before and 0.0643 after correction.
The Ratio of minimum to maximum transmission is 0.7001.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.010
_exptl_crystal_size_mid          0.008
_exptl_crystal_size_min          0.004
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 665 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0666
_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)+(0.0560P)²+0.6264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1619
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1888
_reflns_number_total             2834
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc04733a2.cif
_cod_data_source_block           dyy_2_a
_cod_database_code               1575835
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1A-C17 \\sim S1-C17
 with sigma of 0.005
 C18A-C17 \\sim C18-C17
 with sigma of 0.005
 C20A-C19A \\sim C20-C19
 with sigma of 0.005
 S1A-C20A \\sim S1-C20
 with sigma of 0.005
 C19A-C18A \\sim C19-C18
 with sigma of 0.005
 C13A-C12A \\sim C13-C12
 with sigma of 0.005
 C12A-C11 \\sim C12-C11
 with sigma of 0.005
 C14A-C13A \\sim C14-C13
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(S1) = Uanis(S1A)
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C20) = Uanis(C20A)
Uanis(C13) = Uanis(C13A)
Uanis(C12) = Uanis(C12A)
Uanis(C14) = Uanis(C14A)
Uanis(C20) = Uanis(C19)
4. Others
 Sof(S1A)=Sof(C18A)=Sof(H18A)=1-FVAR(1)
 Sof(S1)=Sof(C18)=Sof(H18)=FVAR(1)
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=1-FVAR(2)
 Sof(C20)=Sof(H20)=Sof(C19)=Sof(H19)=FVAR(2)
 Sof(H11A)=Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C13A)=Sof(H13C)=
 Sof(H13D)=Sof(C12A)=Sof(H12C)=Sof(H12D)=1-FVAR(3)
 Sof(H11)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C11(H11A)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B), C13A(H13C,H13D), C12A(H12C,H12D)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C6(H6), C3(H3), C2(H2), C4(H4), C10(H10), C9(H9), C20(H20),
 C19(H19), C18(H18), C18A(H18A), C19A(H19A), C20A(H20A)
5.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14A(H14D,H14E,H14F)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
N1 N 0.1129(9) 0.6553(6) 0.4207(3) 0.0291(13) Uani 1 1 d . . . . .
C1 C 0.2011(13) 0.7230(8) 0.3556(4) 0.0372(17) Uani 1 1 d . . . . .
H1 H 0.350115 0.774078 0.352987 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2394(11) 0.6541(7) 0.4955(3) 0.0270(14) Uani 1 1 d . . . . .
C7 C 0.2882(12) 0.5548(7) 0.6248(4) 0.0310(15) Uani 1 1 d . . . . .
H7 H 0.229998 0.491824 0.664716 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1606(12) 0.5583(7) 0.5543(4) 0.0323(16) Uani 1 1 d . . . . .
H6 H 0.019886 0.495836 0.545670 0.039 Uiso 1 1 calc R U . . .
C3 C -0.1612(13) 0.6197(8) 0.3248(4) 0.0381(17) Uani 1 1 d . . . . .
H3 H -0.303625 0.588697 0.296192 0.046 Uiso 1 1 calc R U . . .
C2 C 0.0291(12) 0.7010(8) 0.2959(4) 0.0387(17) Uani 1 1 d . . . . .
H2 H 0.038148 0.734891 0.244394 0.046 Uiso 1 1 calc R U . . .
C4 C -0.1068(12) 0.5930(8) 0.4007(4) 0.0355(17) Uani 1 1 d . . . . .
H4 H -0.204888 0.540049 0.434332 0.043 Uiso 1 1 calc R U . . .
C10 C 0.4441(12) 0.7444(8) 0.5105(4) 0.0336(16) Uani 1 1 d . . . . .
H10 H 0.497646 0.812347 0.471503 0.040 Uiso 1 1 calc R U . . .
C8 C 0.4973(12) 0.6393(8) 0.6396(3) 0.0326(15) Uani 1 1 d . . . . .
C15 C 0.5616(12) 0.5123(9) 0.7696(4) 0.0386(17) Uani 1 1 d . . . . .
C9 C 0.5717(13) 0.7374(8) 0.5810(4) 0.0365(17) Uani 1 1 d . . . . .
H9 H 0.712020 0.800179 0.589737 0.044 Uiso 1 1 calc R U . . .
C16 C 0.4903(14) 0.4220(8) 0.8169(4) 0.0416(17) Uani 1 1 d . . . . .
C11 C 0.6548(14) 0.6262(9) 0.7152(4) 0.0473(19) Uani 1 1 d D . . . .
H11 H 0.815246 0.588584 0.703891 0.057 Uiso 0.562(10) 1 calc R U P A 1
H11A H 0.799336 0.569478 0.700023 0.057 Uiso 0.438(10) 1 calc R U P A 2
S1 S 0.1710(13) 0.3417(10) 0.9165(6) 0.0522(9) Uani 0.597(6) 1 d D . P B 1
C17 C 0.4087(9) 0.3167(8) 0.8745(4) 0.0442(18) Uani 1 1 d D . . . .
C20 C 0.231(4) 0.162(2) 0.9674(10) 0.059(3) Uani 0.499(12) 1 d D . P B 1
H20 H 0.137438 0.123930 1.006127 0.071 Uiso 0.499(12) 1 calc R U P B 1
C13 C 0.829(2) 0.8156(17) 0.8268(7) 0.053(3) Uani 0.562(10) 1 d D . P A 1
H13A H 0.825682 0.930418 0.845285 0.063 Uiso 0.562(10) 1 calc R U P A 1
H13B H 0.761159 0.744904 0.865249 0.063 Uiso 0.562(10) 1 calc R U P A 1
C12 C 0.673(9) 0.802(2) 0.749(3) 0.076(8) Uani 0.562(10) 1 d D . P A 1
H12A H 0.512603 0.841615 0.756039 0.091 Uiso 0.562(10) 1 calc R U P A 1
H12B H 0.739695 0.874897 0.710852 0.091 Uiso 0.562(10) 1 calc R U P A 1
C14 C 1.084(3) 0.765(2) 0.8201(9) 0.059(3) Uani 0.562(10) 1 d D . P A 1
H14A H 1.156047 0.839326 0.784810 0.089 Uiso 0.562(10) 1 calc R U P A 1
H14B H 1.088650 0.652216 0.800448 0.089 Uiso 0.562(10) 1 calc R U P A 1
H14C H 1.172448 0.770291 0.870589 0.089 Uiso 0.562(10) 1 calc R U P A 1
C19 C 0.414(3) 0.084(2) 0.9476(8) 0.059(3) Uani 0.499(12) 1 d D . P B 1
H19 H 0.464056 -0.017014 0.970711 0.071 Uiso 0.499(12) 1 calc R U P B 1
C18 C 0.539(3) 0.1585(19) 0.8892(12) 0.066(5) Uani 0.597(6) 1 d D . P B 1
H18 H 0.670614 0.117688 0.865533 0.079 Uiso 0.597(6) 1 calc R U P B 1
S1A S 0.5502(10) 0.1871(7) 0.9311(4) 0.0522(9) Uani 0.403(6) 1 d D . P B 2
C18A C 0.188(8) 0.341(7) 0.913(4) 0.066(5) Uani 0.403(6) 1 d D . P B 2
H18A H 0.084031 0.429883 0.900871 0.079 Uiso 0.403(6) 1 calc R U P B 2
C19A C 0.140(4) 0.223(2) 0.9704(10) 0.059(3) Uani 0.501(12) 1 d D . P B 2
H19A H -0.006697 0.208961 0.991733 0.071 Uiso 0.501(12) 1 calc R U P B 2
C20A C 0.329(2) 0.138(2) 0.9882(9) 0.059(3) Uani 0.501(12) 1 d D . P B 2
H20A H 0.343818 0.057942 1.027874 0.071 Uiso 0.501(12) 1 calc R U P B 2
C14A C 1.069(4) 0.868(2) 0.8602(10) 0.059(3) Uani 0.438(10) 1 d D . P A 2
H14D H 1.115899 0.951309 0.824126 0.089 Uiso 0.438(10) 1 calc R U P A 2
H14E H 1.207845 0.833345 0.893423 0.089 Uiso 0.438(10) 1 calc R U P A 2
H14F H 0.951428 0.914332 0.891605 0.089 Uiso 0.438(10) 1 calc R U P A 2
C13A C 0.965(4) 0.720(2) 0.8159(11) 0.053(3) Uani 0.438(10) 1 d D . P A 2
H13C H 0.909365 0.637899 0.851954 0.063 Uiso 0.438(10) 1 calc R U P A 2
H13D H 1.086370 0.667851 0.786929 0.063 Uiso 0.438(10) 1 calc R U P A 2
C12A C 0.753(12) 0.779(2) 0.759(3) 0.076(8) Uani 0.438(10) 1 d D . P A 2
H12C H 0.629252 0.829703 0.787985 0.091 Uiso 0.438(10) 1 calc R U P A 2
H12D H 0.806981 0.861725 0.723185 0.091 Uiso 0.438(10) 1 calc R U P A 2
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'
N N 0.0061 0.0033 '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
C1 N1 C5 124.0(5) . . ?
C4 N1 C1 108.9(5) . . ?
C4 N1 C5 127.2(5) . . ?
N1 C1 H1 126.7 . . ?
C2 C1 N1 106.6(6) . . ?
C2 C1 H1 126.7 . . ?
C6 C5 N1 120.5(6) . . ?
C10 C5 N1 121.0(5) . . ?
C10 C5 C6 118.5(6) . . ?
C6 C7 H7 118.8 . . ?
C6 C7 C8 122.5(6) . . ?
C8 C7 H7 118.8 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(6) . . ?
C7 C6 H6 120.2 . . ?
C2 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
C4 C3 C2 108.2(6) . . ?
C1 C2 C3 107.9(6) . . ?
C1 C2 H2 126.1 . . ?
C3 C2 H2 126.1 . . ?
N1 C4 H4 125.8 . . ?
C3 C4 N1 108.5(6) . . ?
C3 C4 H4 125.8 . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.2(6) . . ?
C9 C10 H10 119.4 . . ?
C7 C8 C9 117.3(6) . . ?
C7 C8 C11 123.8(6) . . ?
C9 C8 C11 118.8(6) . . ?
C16 C15 C11 177.3(7) . . ?
C10 C9 C8 120.9(7) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C15 C16 C17 178.6(8) . . ?
C8 C11 H11 109.0 . . ?
C8 C11 H11A 103.6 . . ?
C8 C11 C12 106.1(9) . . ?
C8 C11 C12A 122.2(12) . . ?
C15 C11 C8 112.9(6) . . ?
C15 C11 H11 109.0 . . ?
C15 C11 H11A 103.6 . . ?
C15 C11 C12 111(2) . . ?
C15 C11 C12A 109(3) . . ?
C12 C11 H11 109.0 . . ?
C12A C11 H11A 103.6 . . ?
C17 S1 C20 89.6(8) . . ?
C16 C17 S1 125.8(5) . . ?
C16 C17 C18 116.8(8) . . ?
C16 C17 S1A 130.5(5) . . ?
C16 C17 C18A 125.6(13) . . ?
C18 C17 S1 116.9(7) . . ?
C18A C17 S1A 101.5(15) . . ?
S1 C20 H20 123.2 . . ?
C19 C20 S1 113.7(13) . . ?
C19 C20 H20 123.2 . . ?
H13A C13 H13B 107.8 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C14 C13 C12 112(2) . . ?
C11 C12 C13 114.3(13) . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C19 H19 121.7 . . ?
C20 C19 C18 116.5(14) . . ?
C18 C19 H19 121.7 . . ?
C17 C18 H18 128.6 . . ?
C19 C18 C17 102.7(12) . . ?
C19 C18 H18 128.6 . . ?
C17 S1A C20A 99.1(6) . . ?
C17 C18A H18A 121.6 . . ?
C19A C18A C17 117(2) . . ?
C19A C18A H18A 121.6 . . ?
C18A C19A H19A 125.6 . . ?
C20A C19A C18A 109(2) . . ?
C20A C19A H19A 125.6 . . ?
S1A C20A H20A 124.1 . . ?
C19A C20A S1A 111.8(14) . . ?
C19A C20A H20A 124.1 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C13A C14A H14D 109.5 . . ?
C13A C14A H14E 109.5 . . ?
C13A C14A H14F 109.5 . . ?
C14A C13A H13C 109.9 . . ?
C14A C13A H13D 109.9 . . ?
C14A C13A C12A 108.9(14) . . ?
H13C C13A H13D 108.3 . . ?
C12A C13A H13C 109.9 . . ?
C12A C13A H13D 109.9 . . ?
C11 C12A C13A 107.1(12) . . ?
C11 C12A H12C 110.3 . . ?
C11 C12A H12D 110.3 . . ?
C13A C12A H12C 110.3 . . ?
C13A C12A H12D 110.3 . . ?
H12C C12A H12D 108.6 . . ?
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
N1 C1 1.399(8) . ?
N1 C5 1.441(7) . ?
N1 C4 1.367(9) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(10) . ?
C5 C6 1.397(8) . ?
C5 C10 1.384(9) . ?
C7 H7 0.9500 . ?
C7 C6 1.378(9) . ?
C7 C8 1.381(9) . ?
C6 H6 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.402(10) . ?
C3 C4 1.357(9) . ?
C2 H2 0.9500 . ?
C4 H4 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.379(10) . ?
C8 C9 1.397(8) . ?
C8 C11 1.538(9) . ?
C15 C16 1.204(9) . ?
C15 C11 1.463(10) . ?
C9 H9 0.9500 . ?
C16 C17 1.433(10) . ?
C11 H11 1.0000 . ?
C11 H11A 1.0000 . ?
C11 C12 1.545(12) . ?
C11 C12A 1.545(13) . ?
S1 C17 1.609(7) . ?
S1 C20 1.732(13) . ?
C17 C18 1.496(15) . ?
C17 S1A 1.616(7) . ?
C17 C18A 1.497(17) . ?
C20 H20 0.9500 . ?
C20 C19 1.30(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C12 1.571(18) . ?
C13 C14 1.526(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C18 1.43(2) . ?
C18 H18 0.9500 . ?
S1A C20A 1.724(13) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.43(2) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.30(2) . ?
C20A H20A 0.9500 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C14A C13A 1.526(15) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C13A C12A 1.571(19) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
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
N1 C1 C2 C3 -0.3(7) . . . . ?
N1 C5 C6 C7 177.9(5) . . . . ?
N1 C5 C10 C9 -176.8(6) . . . . ?
C1 N1 C5 C6 -167.9(6) . . . . ?
C1 N1 C5 C10 10.5(8) . . . . ?
C1 N1 C4 C3 -0.2(7) . . . . ?
C5 N1 C1 C2 -179.7(5) . . . . ?
C5 N1 C4 C3 179.8(5) . . . . ?
C5 C10 C9 C8 -0.3(10) . . . . ?
C7 C8 C9 C10 -2.1(10) . . . . ?
C7 C8 C11 C15 0.9(10) . . . . ?
C7 C8 C11 C12 -121(3) . . . . ?
C7 C8 C11 C12A -132(4) . . . . ?
C6 C5 C10 C9 1.6(9) . . . . ?
C6 C7 C8 C9 3.2(9) . . . . ?
C6 C7 C8 C11 -174.4(6) . . . . ?
C2 C3 C4 N1 0.0(7) . . . . ?
C4 N1 C1 C2 0.3(7) . . . . ?
C4 N1 C5 C6 12.1(8) . . . . ?
C4 N1 C5 C10 -169.5(6) . . . . ?
C4 C3 C2 C1 0.2(7) . . . . ?
C10 C5 C6 C7 -0.5(9) . . . . ?
C8 C7 C6 C5 -2.0(9) . . . . ?
C8 C11 C12 C13 -180(3) . . . . ?
C8 C11 C12A C13A -162(3) . . . . ?
C15 C11 C12 C13 57(4) . . . . ?
C15 C11 C12A C13A 64(5) . . . . ?
C9 C8 C11 C15 -176.7(6) . . . . ?
C9 C8 C11 C12 62(3) . . . . ?
C9 C8 C11 C12A 51(4) . . . . ?
C16 C17 C18 C19 -179.5(11) . . . . ?
C16 C17 S1A C20A 172.3(9) . . . . ?
C16 C17 C18A C19A -179(3) . . . . ?
C11 C8 C9 C10 175.7(6) . . . . ?
S1 C17 C18 C19 -7.3(18) . . . . ?
S1 C20 C19 C18 1(3) . . . . ?
C17 S1 C20 C19 -4.6(17) . . . . ?
C17 S1A C20A C19A -3.5(18) . . . . ?
C17 C18A C19A C20A 14(7) . . . . ?
C20 S1 C17 C16 178.3(9) . . . . ?
C20 S1 C17 C18 7.0(14) . . . . ?
C20 C19 C18 C17 4(2) . . . . ?
C14 C13 C12 C11 61(5) . . . . ?
S1A C17 C18A C19A -15(6) . . . . ?
C18A C17 S1A C20A 10(3) . . . . ?
C18A C19A C20A S1A -5(4) . . . . ?
C14A C13A C12A C11 179(4) . . . . ?
