#------------------------------------------------------------------------------
#$Date: 2022-07-30 00:50:49 +0300 (Sat, 30 Jul 2022) $
#$Revision: 276998 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/04/7130442.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_7130442
loop_
_publ_author_name
'Wang, Qing'
'Wang, Sen-Lin'
'Fan, Jin-Bao'
'Zeng, Guang-Yao'
'Zhou, Ying-Jun'
'Deng, Xu'
_publ_section_title
;
 Acid-promoted intra- and intermolecular [2+2] cycloaddition of indoles to
 aryl alkynes to access cyclobutene-fused indolines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02840A
_journal_year                    2022
_chemical_formula_moiety         'C20 H19 N'
_chemical_formula_sum            'C20 H19 N'
_chemical_formula_weight         273.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2022-04-23
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-05-18 deposited with the CCDC.	2022-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                107.989(2)
_cell_angle_beta                 94.9730(10)
_cell_angle_gamma                92.730(2)
_cell_formula_units_Z            2
_cell_length_a                   8.71530(10)
_cell_length_b                   9.2902(2)
_cell_length_c                   9.50980(10)
_cell_measurement_reflns_used    5445
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.5540
_cell_measurement_theta_min      4.9250
_cell_volume                     727.33(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     56.00  82.00   0.50    0.50    --   42.30 -77.00-150.00   52
  2  ω     85.00 110.00   0.50    0.50    --   42.30  77.00 120.00   50
  3  ω     23.00  57.00   0.50    0.50    --   42.30 -57.00   0.00   68
  4  ω     83.00 126.00   0.50    0.50    --   42.30  77.00 -60.00   86
  5  ω    -24.00  82.00   0.50    0.50    --   42.30 -82.00 150.00  212
  6  ω     42.00  83.00   0.50    0.50    --   42.30 -82.00 -60.00   82
  7  ω    -41.00  37.00   0.50    0.50    --   42.30 -77.00-150.00  156
  8  ω    -31.00  38.00   0.50    0.50    --   42.30 -82.00 -60.00  138
  9  ω     82.00 132.00   0.50    0.50    --   42.30  77.00-150.00  100
 10  ω     60.00 146.00   0.50    0.50    --  102.30 -82.00-120.00  172
 11  ω     19.00  44.00   0.50    0.50    --  102.30 -82.00-120.00   50
 12  ω     50.00  94.00   0.50    0.50    --  102.30 -82.00  30.00   88
 13  ω     76.00 146.00   0.50    0.50    --  102.30 -82.00  60.00  140
 14  ω    110.00 146.00   0.50    0.50    --  102.30  82.00 -60.00   72
 15  ω     13.00  96.00   0.50    0.50    --  102.30 -63.00-150.00  166
 16  ω     16.00  41.00   0.50    0.50    --  102.30 -82.00 -60.00   50
 17  ω     77.00 106.00   0.50    0.50    --  102.30 -82.00 120.00   58
 18  ω     14.00 133.00   0.50    0.50    --  102.30 -63.00  30.00  238
 19  ω     27.00  52.00   0.50    0.50    --  102.30 -82.00 120.00   50
 20  ω     68.00 172.00   0.50    0.50    --  102.30 -12.00 -60.00  208
 21  ω     13.00  63.00   0.50    0.50    --  102.30 -12.00 -60.00  100
 22  ω     86.00 122.00   0.50    0.50    --  102.30 -82.00 -60.00   72
 23  ω     14.00 184.00   0.50    0.50    --  102.30  12.00   0.00  340
 24  ω     99.00 134.00   0.50    0.50    --  102.30 -63.00-150.00   70
 25  ω    165.00 190.00   0.50    0.50    --  102.30  82.00  90.00   50
 26  ω     43.00 103.00   0.50    0.50    --  102.30 -82.00-180.00  120
 27  ω     67.00 141.00   0.50    0.50    --  102.30 -38.00  30.00  148
 28  ω     98.00 124.00   0.50    0.50    --  102.30 -82.00  90.00   52
 29  ω     30.00  55.00   0.50    0.50    --  102.30 -38.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1565372000
_diffrn_orient_matrix_UB_12      0.0009949000
_diffrn_orient_matrix_UB_13      -0.0636651000
_diffrn_orient_matrix_UB_21      0.0711161000
_diffrn_orient_matrix_UB_22      -0.0711680000
_diffrn_orient_matrix_UB_23      0.1144880000
_diffrn_orient_matrix_UB_31      -0.0460053000
_diffrn_orient_matrix_UB_32      -0.1597509000
_diffrn_orient_matrix_UB_33      -0.1103793000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6281
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.998
_diffrn_reflns_theta_min         4.918
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0218(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0375
_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)+(0.0473P)²+0.2390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2617
_reflns_number_total             2750
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02840a2.cif
_cod_data_source_block           8
_cod_database_code               7130442
_shelx_shelxl_version_number     2017/1
_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   0.947
_shelx_estimated_absorpt_t_min   0.928
_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.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 1.557
_oxdiff_exptl_absorpt_empirical_full_min 0.628
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
N1 N 0.48413(11) 0.71017(11) 0.85515(10) 0.0262(2) Uani 1 1 d . . . . .
C1 C 0.62276(13) 0.63741(13) 0.83792(12) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.65129(14) 0.49989(14) 0.86027(13) 0.0289(3) Uani 1 1 d . . . . .
H2 H 0.572046 0.439421 0.878278 0.035 Uiso 1 1 calc R U . . .
C3 C 0.80097(14) 0.45470(14) 0.85510(14) 0.0317(3) Uani 1 1 d . . . . .
H3 H 0.821604 0.362923 0.870104 0.038 Uiso 1 1 calc R U . . .
C4 C 0.91995(14) 0.54328(15) 0.82813(14) 0.0320(3) Uani 1 1 d . . . . .
H4 H 1.019438 0.511225 0.825653 0.038 Uiso 1 1 calc R U . . .
C5 C 0.89042(13) 0.68054(14) 0.80468(13) 0.0285(3) Uani 1 1 d . . . . .
H5 H 0.970154 0.740717 0.787001 0.034 Uiso 1 1 calc R U . . .
C6 C 0.74177(13) 0.72703(13) 0.80780(12) 0.0238(2) Uani 1 1 d . . . . .
C7 C 0.67967(13) 0.86805(13) 0.78293(12) 0.0251(3) Uani 1 1 d . . . . .
C8 C 0.61507(13) 0.83875(12) 0.61928(12) 0.0249(3) Uani 1 1 d . . . . .
C9 C 0.46830(13) 0.81123(13) 0.64408(13) 0.0266(3) Uani 1 1 d . . . . .
C10 C 0.50594(13) 0.84585(13) 0.80843(12) 0.0259(3) Uani 1 1 d . . . . .
H10 H 0.462791 0.936773 0.869956 0.031 Uiso 1 1 calc R U . . .
C11 C 0.33513(13) 0.62343(15) 0.78929(14) 0.0311(3) Uani 1 1 d . . . . .
H11A H 0.252481 0.681531 0.834252 0.037 Uiso 1 1 calc R U . . .
H11B H 0.331363 0.529514 0.813804 0.037 Uiso 1 1 calc R U . . .
C12 C 0.30561(14) 0.58519(15) 0.61981(14) 0.0349(3) Uani 1 1 d . . . . .
H12A H 0.202631 0.535228 0.586804 0.042 Uiso 1 1 calc R U . . .
H12B H 0.378748 0.514441 0.573704 0.042 Uiso 1 1 calc R U . . .
C13 C 0.32021(14) 0.72579(16) 0.56688(14) 0.0342(3) Uani 1 1 d . . . . .
H13A H 0.321987 0.695506 0.459890 0.041 Uiso 1 1 calc R U . . .
H13B H 0.234105 0.787667 0.593146 0.041 Uiso 1 1 calc R U . . .
C14 C 0.69202(13) 0.83088(12) 0.48653(12) 0.0255(3) Uani 1 1 d . . . . .
C15 C 0.60510(14) 0.82526(13) 0.35391(13) 0.0295(3) Uani 1 1 d . . . . .
H15 H 0.498656 0.830458 0.351683 0.035 Uiso 1 1 calc R U . . .
C16 C 0.67547(15) 0.81205(14) 0.22599(14) 0.0329(3) Uani 1 1 d . . . . .
H16 H 0.615933 0.806849 0.138280 0.040 Uiso 1 1 calc R U . . .
C17 C 0.83398(16) 0.80655(14) 0.22800(14) 0.0349(3) Uani 1 1 d . . . . .
H17 H 0.880965 0.796350 0.141649 0.042 Uiso 1 1 calc R U . . .
C18 C 0.92205(15) 0.81629(16) 0.35910(15) 0.0361(3) Uani 1 1 d . . . . .
H18 H 1.028838 0.814654 0.361418 0.043 Uiso 1 1 calc R U . . .
C19 C 0.85176(14) 0.82851(14) 0.48728(13) 0.0312(3) Uani 1 1 d . . . . .
H19 H 0.912157 0.835203 0.574953 0.037 Uiso 1 1 calc R U . . .
C20 C 0.77163(15) 1.01669(14) 0.86805(14) 0.0338(3) Uani 1 1 d . . . . .
H20A H 0.788512 1.024473 0.971326 0.051 Uiso 1 1 calc R U . . .
H20B H 0.715285 1.099728 0.857516 0.051 Uiso 1 1 calc R U . . .
H20C H 0.869340 1.020027 0.829219 0.051 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'
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 C10 106.71(9) . . ?
C1 N1 C11 120.06(10) . . ?
C10 N1 C11 111.81(9) . . ?
C2 C1 N1 126.77(10) . . ?
C2 C1 C6 120.68(11) . . ?
C6 C1 N1 112.29(10) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.47(11) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.42(11) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.86(11) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.68(11) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C7 110.30(10) . . ?
C5 C6 C1 119.86(11) . . ?
C5 C6 C7 129.84(10) . . ?
C6 C7 C8 111.79(9) . . ?
C6 C7 C10 100.86(9) . . ?
C8 C7 C10 84.43(8) . . ?
C20 C7 C6 115.71(10) . . ?
C20 C7 C8 119.72(10) . . ?
C20 C7 C10 119.14(10) . . ?
C9 C8 C7 93.72(9) . . ?
C9 C8 C14 134.44(11) . . ?
C14 C8 C7 131.61(10) . . ?
C8 C9 C10 94.46(9) . . ?
C8 C9 C13 141.17(11) . . ?
C13 C9 C10 120.83(10) . . ?
N1 C10 C7 108.93(9) . . ?
N1 C10 C9 112.05(9) . . ?
N1 C10 H10 115.1 . . ?
C7 C10 H10 115.1 . . ?
C9 C10 C7 87.17(8) . . ?
C9 C10 H10 115.1 . . ?
N1 C11 H11A 108.7 . . ?
N1 C11 H11B 108.7 . . ?
N1 C11 C12 114.33(9) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C11 C12 C13 113.25(10) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C9 C13 C12 105.73(10) . . ?
C9 C13 H13A 110.6 . . ?
C9 C13 H13B 110.6 . . ?
C12 C13 H13A 110.6 . . ?
C12 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C15 C14 C8 120.15(11) . . ?
C19 C14 C8 121.82(10) . . ?
C19 C14 C15 118.03(10) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.85(11) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.30(11) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.59(11) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.24(12) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 120.94(11) . . ?
C18 C19 H19 119.5 . . ?
C7 C20 H20A 109.5 . . ?
C7 C20 H20B 109.5 . . ?
C7 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
N1 C1 1.4097(14) . ?
N1 C10 1.4698(15) . ?
N1 C11 1.4750(15) . ?
C1 C2 1.3886(16) . ?
C1 C6 1.4027(16) . ?
C2 H2 0.9300 . ?
C2 C3 1.3896(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.3832(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.3925(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.3848(16) . ?
C6 C7 1.5173(15) . ?
C7 C8 1.5443(15) . ?
C7 C10 1.5680(15) . ?
C7 C20 1.5152(16) . ?
C8 C9 1.3475(16) . ?
C8 C14 1.4640(15) . ?
C9 C10 1.4980(15) . ?
C9 C13 1.4877(17) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.5349(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5418(19) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.3989(16) . ?
C14 C19 1.3928(16) . ?
C15 H15 0.9300 . ?
C15 C16 1.3840(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.3836(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.3819(19) . ?
C18 H18 0.9300 . ?
C18 C19 1.3873(17) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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 -172.40(11) . . . . ?
N1 C1 C6 C5 172.57(10) . . . . ?
N1 C1 C6 C7 -7.33(13) . . . . ?
N1 C11 C12 C13 -54.37(14) . . . . ?
C1 N1 C10 C7 -8.70(11) . . . . ?
C1 N1 C10 C9 86.04(11) . . . . ?
C1 N1 C11 C12 -74.26(13) . . . . ?
C1 C2 C3 C4 -0.13(18) . . . . ?
C1 C6 C7 C8 -86.78(11) . . . . ?
C1 C6 C7 C10 1.52(11) . . . . ?
C1 C6 C7 C20 131.51(10) . . . . ?
C2 C1 C6 C5 -1.97(17) . . . . ?
C2 C1 C6 C7 178.13(10) . . . . ?
C2 C3 C4 C5 -0.35(19) . . . . ?
C3 C4 C5 C6 -0.33(18) . . . . ?
C4 C5 C6 C1 1.47(17) . . . . ?
C4 C5 C6 C7 -178.65(11) . . . . ?
C5 C6 C7 C8 93.33(14) . . . . ?
C5 C6 C7 C10 -178.37(11) . . . . ?
C5 C6 C7 C20 -48.38(16) . . . . ?
C6 C1 C2 C3 1.29(17) . . . . ?
C6 C7 C8 C9 95.94(10) . . . . ?
C6 C7 C8 C14 -79.11(14) . . . . ?
C6 C7 C10 N1 4.39(11) . . . . ?
C6 C7 C10 C9 -107.97(9) . . . . ?
C7 C8 C9 C10 3.71(9) . . . . ?
C7 C8 C9 C13 -152.74(16) . . . . ?
C7 C8 C14 C15 -170.31(11) . . . . ?
C7 C8 C14 C19 9.80(18) . . . . ?
C8 C7 C10 N1 115.55(9) . . . . ?
C8 C7 C10 C9 3.19(8) . . . . ?
C8 C9 C10 N1 -112.95(10) . . . . ?
C8 C9 C10 C7 -3.65(9) . . . . ?
C8 C9 C13 C12 103.32(17) . . . . ?
C8 C14 C15 C16 -177.55(10) . . . . ?
C8 C14 C19 C18 177.99(11) . . . . ?
C9 C8 C14 C15 16.61(19) . . . . ?
C9 C8 C14 C19 -163.29(13) . . . . ?
C10 N1 C1 C2 -175.85(11) . . . . ?
C10 N1 C1 C6 10.01(12) . . . . ?
C10 N1 C11 C12 51.85(13) . . . . ?
C10 C7 C8 C9 -3.55(9) . . . . ?
C10 C7 C8 C14 -178.61(12) . . . . ?
C10 C9 C13 C12 -49.04(14) . . . . ?
C11 N1 C1 C2 -47.40(16) . . . . ?
C11 N1 C1 C6 138.47(10) . . . . ?
C11 N1 C10 C7 -141.81(9) . . . . ?
C11 N1 C10 C9 -47.07(12) . . . . ?
C11 C12 C13 C9 48.51(13) . . . . ?
C13 C9 C10 N1 50.09(14) . . . . ?
C13 C9 C10 C7 159.39(11) . . . . ?
C14 C8 C9 C10 178.53(12) . . . . ?
C14 C8 C9 C13 22.1(3) . . . . ?
C14 C15 C16 C17 -1.00(18) . . . . ?
C15 C14 C19 C18 -1.91(18) . . . . ?
C15 C16 C17 C18 -0.83(19) . . . . ?
C16 C17 C18 C19 1.3(2) . . . . ?
C17 C18 C19 C14 0.1(2) . . . . ?
C19 C14 C15 C16 2.35(17) . . . . ?
C20 C7 C8 C9 -124.06(11) . . . . ?
C20 C7 C8 C14 60.88(16) . . . . ?
C20 C7 C10 N1 -123.40(11) . . . . ?
C20 C7 C10 C9 124.24(11) . . . . ?
