#------------------------------------------------------------------------------
#$Date: 2024-07-05 20:37:56 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293197 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/32/7063263.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_7063263
loop_
_publ_author_name
'Xiang, Zixin'
'Zhang, Simiao'
'Zhang, Ziyi'
'Liu, Hang'
'Wang, Junqi'
'Chen, Wenwen'
'Wang, Yong'
'Wan, Xiaobing'
_publ_section_title
;
 Vicinal difunctionalization of nitriles: modular construction of N-alkyl
 amidines and late-stage modification
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11834
_journal_page_last               11843
_journal_paper_doi               10.1039/D4NJ02051K
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C20 H25 Br N2 O2 S'
_chemical_formula_sum            'C20 H25 Br N2 O2 S'
_chemical_formula_weight         437.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2hjl9y
_audit_creation_date             2023-11-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-23 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.570(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8785(8)
_cell_length_b                   11.3457(5)
_cell_length_c                   11.5314(6)
_cell_measurement_reflns_used    5874
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      29.5540
_cell_measurement_theta_min      2.2370
_cell_volume                     2010.61(18)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  37.00   1.00    2.50    --   12.72 -37.00  90.00   99
  2  ω    -12.00  87.00   1.00    2.50    --   12.72  37.00 -90.00   99
  3  ω     39.00 101.00   1.00    2.50    --   12.72 178.00 120.00   62
  4  ω    -75.00 -25.00   1.00    2.50    --   12.72   0.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0385425000
_diffrn_orient_matrix_UB_12      0.0239398000
_diffrn_orient_matrix_UB_13      0.0109782000
_diffrn_orient_matrix_UB_21      -0.0099916000
_diffrn_orient_matrix_UB_22      0.0270904000
_diffrn_orient_matrix_UB_23      -0.0572750000
_diffrn_orient_matrix_UB_31      -0.0233818000
_diffrn_orient_matrix_UB_32      -0.0509864000
_diffrn_orient_matrix_UB_33      -0.0252504000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17520
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.561
_diffrn_reflns_theta_min         2.231
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0044(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         5243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0466
_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)+(0.0481P)²+0.6872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3471
_reflns_number_total             5243
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj02051k2.cif
_cod_data_source_block           g231102c_auto
_cod_depositor_comments          'Adding full bibliography for 7063263.cif.'
_cod_original_cell_volume        2010.61(17)
_cod_database_code               7063263
_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_max   0.881
_shelx_estimated_absorpt_t_min   0.478
_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.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), N2(H2), C10(H10), C6(H6), C20(H20), C17(H17), C19(H19), C9(H9),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C4(H4A,H4B,H4C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.173
_oxdiff_exptl_absorpt_empirical_full_min 0.743
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Br1 Br 0.33830(2) 0.02495(3) 0.41301(3) 0.06244(15) Uani 1 1 d . . . . .
S1 S -0.10197(4) 0.30201(5) -0.41481(5) 0.02905(16) Uani 1 1 d . . . . .
O2 O -0.09753(12) 0.17802(15) -0.44063(16) 0.0395(5) Uani 1 1 d . . . . .
O1 O -0.10161(11) 0.37976(15) -0.51363(14) 0.0353(4) Uani 1 1 d . . . . .
N1 N -0.02651(12) 0.32514(17) -0.29552(17) 0.0289(5) Uani 1 1 d . . . . .
C5 C -0.35853(15) 0.3518(2) -0.3101(2) 0.0287(5) Uani 1 1 d . . . . .
C8 C -0.20020(15) 0.3259(2) -0.3725(2) 0.0290(5) Uani 1 1 d . . . . .
C7 C -0.26783(16) 0.3873(2) -0.4467(2) 0.0311(5) Uani 1 1 d . . . . .
H7 H -0.260824 0.420820 -0.518234 0.037 Uiso 1 1 calc R U . . .
N2 N 0.05076(13) 0.44306(18) -0.14953(17) 0.0308(5) Uani 1 1 d . . . . .
H2 H 0.066302 0.513593 -0.123011 0.037 Uiso 1 1 calc R U . . .
C13 C 0.08807(16) 0.3432(2) -0.0749(2) 0.0319(6) Uani 1 1 d . . . . .
H13A H 0.127886 0.300167 -0.112250 0.038 Uiso 1 1 calc R U . . .
H13B H 0.041753 0.289240 -0.066660 0.038 Uiso 1 1 calc R U . . .
C1 C -0.44673(16) 0.3650(2) -0.2798(2) 0.0342(6) Uani 1 1 d . . . . .
C11 C -0.00544(15) 0.4328(2) -0.2554(2) 0.0271(5) Uani 1 1 d . . . . .
C18 C 0.27674(17) 0.1356(3) 0.2991(2) 0.0387(6) Uani 1 1 d . . . . .
C12 C -0.03814(18) 0.5460(2) -0.3168(2) 0.0358(6) Uani 1 1 d . . . . .
H12A H -0.019440 0.552493 -0.390439 0.054 Uiso 1 1 calc R U . . .
H12B H -0.014981 0.611683 -0.264629 0.054 Uiso 1 1 calc R U . . .
H12C H -0.101199 0.547369 -0.335267 0.054 Uiso 1 1 calc R U . . .
C10 C -0.28814(17) 0.2942(2) -0.2354(2) 0.0402(7) Uani 1 1 d . . . . .
H10 H -0.293984 0.263818 -0.161959 0.048 Uiso 1 1 calc R U . . .
C6 C -0.34563(15) 0.3992(2) -0.4153(2) 0.0324(6) Uani 1 1 d . . . . .
H6 H -0.391352 0.440715 -0.466748 0.039 Uiso 1 1 calc R U . . .
C14 C 0.13679(19) 0.3880(2) 0.0470(2) 0.0421(7) Uani 1 1 d . . . . .
H14A H 0.178402 0.448034 0.035724 0.051 Uiso 1 1 calc R U . . .
H14B H 0.095037 0.426853 0.084225 0.051 Uiso 1 1 calc R U . . .
C20 C 0.24769(18) 0.3336(3) 0.2336(2) 0.0421(7) Uani 1 1 d . . . . .
H20 H 0.259245 0.414546 0.245235 0.051 Uiso 1 1 calc R U . . .
C4 C -0.44785(19) 0.3060(3) -0.1614(2) 0.0438(7) Uani 1 1 d . . . . .
H4A H -0.438230 0.222005 -0.167062 0.066 Uiso 1 1 calc R U . . .
H4B H -0.503840 0.319193 -0.144185 0.066 Uiso 1 1 calc R U . . .
H4C H -0.402199 0.339297 -0.097613 0.066 Uiso 1 1 calc R U . . .
C15 C 0.18557(16) 0.2965(2) 0.1330(2) 0.0323(6) Uani 1 1 d . . . . .
C2 C -0.4674(2) 0.4961(3) -0.2715(3) 0.0489(8) Uani 1 1 d . . . . .
H2A H -0.423401 0.532261 -0.207602 0.073 Uiso 1 1 calc R U . . .
H2B H -0.524011 0.504596 -0.254701 0.073 Uiso 1 1 calc R U . . .
H2C H -0.468034 0.534404 -0.346862 0.073 Uiso 1 1 calc R U . . .
C17 C 0.21514(18) 0.0952(3) 0.2004(2) 0.0406(6) Uani 1 1 d . . . . .
H17 H 0.203812 0.014160 0.189174 0.049 Uiso 1 1 calc R U . . .
C19 C 0.29305(18) 0.2542(3) 0.3172(2) 0.0448(7) Uani 1 1 d . . . . .
H19 H 0.334492 0.280806 0.385429 0.054 Uiso 1 1 calc R U . . .
C9 C -0.20993(17) 0.2801(3) -0.2656(2) 0.0413(7) Uani 1 1 d . . . . .
H9 H -0.163723 0.239716 -0.213925 0.050 Uiso 1 1 calc R U . . .
C16 C 0.17036(17) 0.1763(2) 0.1181(2) 0.0393(7) Uani 1 1 d . . . . .
H16 H 0.128535 0.149354 0.050404 0.047 Uiso 1 1 calc R U . . .
C3 C -0.51731(19) 0.3071(3) -0.3801(3) 0.0515(8) Uani 1 1 d . . . . .
H3A H -0.519936 0.346969 -0.455392 0.077 Uiso 1 1 calc R U . . .
H3B H -0.573258 0.313352 -0.361056 0.077 Uiso 1 1 calc R U . . .
H3C H -0.503170 0.224703 -0.387146 0.077 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N1 105.78(10) . . ?
O2 S1 C8 107.39(11) . . ?
O1 S1 O2 115.03(11) . . ?
O1 S1 N1 115.30(10) . . ?
O1 S1 C8 107.66(11) . . ?
N1 S1 C8 105.00(11) . . ?
C11 N1 S1 121.45(17) . . ?
C10 C5 C1 122.8(2) . . ?
C6 C5 C1 120.4(2) . . ?
C6 C5 C10 116.8(2) . . ?
C7 C8 S1 120.6(2) . . ?
C7 C8 C9 119.9(2) . . ?
C9 C8 S1 119.52(19) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 H7 120.2 . . ?
C13 N2 H2 118.1 . . ?
C11 N2 H2 118.1 . . ?
C11 N2 C13 123.8(2) . . ?
N2 C13 H13A 109.9 . . ?
N2 C13 H13B 109.9 . . ?
N2 C13 C14 109.0(2) . . ?
H13A C13 H13B 108.3 . . ?
C14 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
C5 C1 C3 108.7(2) . . ?
C4 C1 C5 112.2(2) . . ?
C4 C1 C2 108.6(2) . . ?
C4 C1 C3 108.4(2) . . ?
C2 C1 C5 109.4(2) . . ?
C2 C1 C3 109.5(2) . . ?
N1 C11 N2 117.2(2) . . ?
N1 C11 C12 127.0(2) . . ?
N2 C11 C12 115.8(2) . . ?
C17 C18 Br1 119.1(2) . . ?
C19 C18 Br1 119.8(2) . . ?
C19 C18 C17 121.1(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C10 H10 118.9 . . ?
C9 C10 C5 122.1(2) . . ?
C9 C10 H10 118.9 . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 122.0(2) . . ?
C7 C6 H6 119.0 . . ?
C13 C14 H14A 108.3 . . ?
C13 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 C13 116.0(2) . . ?
C15 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C15 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C15 121.5(3) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C20 C15 C14 118.7(2) . . ?
C20 C15 C16 117.8(2) . . ?
C16 C15 C14 123.4(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C18 C17 H17 120.6 . . ?
C18 C17 C16 118.8(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C19 C20 119.1(2) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.7(2) . . ?
C17 C16 H16 119.2 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 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
Br1 C18 1.900(3) . ?
S1 O2 1.4433(18) . ?
S1 O1 1.4422(18) . ?
S1 N1 1.6023(19) . ?
S1 C8 1.768(3) . ?
N1 C11 1.319(3) . ?
C5 C1 1.534(4) . ?
C5 C10 1.391(3) . ?
C5 C6 1.389(3) . ?
C8 C7 1.381(3) . ?
C8 C9 1.382(3) . ?
C7 H7 0.9400 . ?
C7 C6 1.378(3) . ?
N2 H2 0.8700 . ?
N2 C13 1.455(3) . ?
N2 C11 1.323(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 C14 1.513(3) . ?
C1 C4 1.524(4) . ?
C1 C2 1.532(4) . ?
C1 C3 1.541(4) . ?
C11 C12 1.496(3) . ?
C18 C17 1.379(4) . ?
C18 C19 1.376(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C10 H10 0.9400 . ?
C10 C9 1.381(4) . ?
C6 H6 0.9400 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 C15 1.509(4) . ?
C20 H20 0.9400 . ?
C20 C15 1.385(3) . ?
C20 C19 1.382(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C15 C16 1.388(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C17 H17 0.9400 . ?
C17 C16 1.383(4) . ?
C19 H19 0.9400 . ?
C9 H9 0.9400 . ?
C16 H16 0.9400 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
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
Br1 C18 C17 C16 179.7(2) . . . . ?
Br1 C18 C19 C20 -179.9(2) . . . . ?
S1 N1 C11 N2 172.74(17) . . . . ?
S1 N1 C11 C12 -7.4(4) . . . . ?
S1 C8 C7 C6 176.28(19) . . . . ?
S1 C8 C9 C10 -177.0(2) . . . . ?
O2 S1 N1 C11 171.42(19) . . . . ?
O2 S1 C8 C7 -110.1(2) . . . . ?
O2 S1 C8 C9 68.2(2) . . . . ?
O1 S1 N1 C11 43.1(2) . . . . ?
O1 S1 C8 C7 14.3(2) . . . . ?
O1 S1 C8 C9 -167.4(2) . . . . ?
N1 S1 C8 C7 137.6(2) . . . . ?
N1 S1 C8 C9 -44.0(2) . . . . ?
C5 C10 C9 C8 1.0(4) . . . . ?
C8 S1 N1 C11 -75.2(2) . . . . ?
C8 C7 C6 C5 0.4(4) . . . . ?
C7 C8 C9 C10 1.4(4) . . . . ?
N2 C13 C14 C15 -175.5(2) . . . . ?
C13 N2 C11 N1 -1.7(4) . . . . ?
C13 N2 C11 C12 178.4(2) . . . . ?
C13 C14 C15 C20 164.6(3) . . . . ?
C13 C14 C15 C16 -16.8(4) . . . . ?
C1 C5 C10 C9 178.1(2) . . . . ?
C1 C5 C6 C7 -178.8(2) . . . . ?
C11 N2 C13 C14 -170.4(2) . . . . ?
C18 C17 C16 C15 -0.4(4) . . . . ?
C10 C5 C1 C4 -1.2(3) . . . . ?
C10 C5 C1 C2 119.5(3) . . . . ?
C10 C5 C1 C3 -121.1(3) . . . . ?
C10 C5 C6 C7 1.8(4) . . . . ?
C6 C5 C1 C4 179.5(2) . . . . ?
C6 C5 C1 C2 -59.9(3) . . . . ?
C6 C5 C1 C3 59.6(3) . . . . ?
C6 C5 C10 C9 -2.5(4) . . . . ?
C14 C15 C16 C17 -178.6(3) . . . . ?
C20 C15 C16 C17 0.1(4) . . . . ?
C15 C20 C19 C18 0.8(4) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C19 C18 C17 C16 0.9(4) . . . . ?
C19 C20 C15 C14 178.4(3) . . . . ?
C19 C20 C15 C16 -0.3(4) . . . . ?
C9 C8 C7 C6 -2.0(4) . . . . ?
