#------------------------------------------------------------------------------
#$Date: 2023-07-05 11:51:30 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284845 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/16/7131631.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_7131631
loop_
_publ_author_name
'Li, Cheng'
'Zhao, Bin'
'Mao, Guojiang'
'Deng, Guo-Jun'
_publ_section_title
;
 Rhodium(III)-catalyzed mild and regioselective dearomative
 spirocyclization of 2-aryl-3-nitrosoindoles with alkynes.
;
_journal_issue                   46
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7044
_journal_page_last               7047
_journal_paper_doi               10.1039/d3cc01940c
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C31 H22 N2 O'
_chemical_formula_sum            'C31 H22 N2 O'
_chemical_formula_weight         438.50
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-02
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-03-13 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.132(9)
_cell_angle_beta                 110.122(10)
_cell_angle_gamma                104.018(10)
_cell_formula_units_Z            2
_cell_length_a                   10.2696(12)
_cell_length_b                   10.3708(13)
_cell_length_c                   12.6585(13)
_cell_measurement_reflns_used    3121
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      28.1930
_cell_measurement_theta_min      2.5520
_cell_volume                     1222.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  61.00   1.00    5.00    --  -11.27  77.00 120.00  105
  2  ω     28.00  56.00   1.00    5.00    --  -11.27  77.00   0.00   28
  3  ω      1.00  77.00   1.00    5.00    --   11.90  77.00  30.00   76
  4  ω    -20.00  86.00   1.00    5.00    --   11.90  77.00 -90.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0274119000
_diffrn_orient_matrix_UB_12      -0.0530444000
_diffrn_orient_matrix_UB_13      -0.0110348000
_diffrn_orient_matrix_UB_21      0.0431653000
_diffrn_orient_matrix_UB_22      0.0436808000
_diffrn_orient_matrix_UB_23      -0.0251123000
_diffrn_orient_matrix_UB_31      0.0564309000
_diffrn_orient_matrix_UB_32      0.0170840000
_diffrn_orient_matrix_UB_33      0.0532967000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8691
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.187
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0653
_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)+(0.0962P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1626
_refine_ls_wR_factor_ref         0.1861
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3009
_reflns_number_total             4303
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc01940c2.cif
_cod_data_source_block           458-2
_cod_depositor_comments
'Adding full bibliography for 7131630--7131631.cif.'
_cod_database_code               7131631
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.82 with sigma of 0.01
 N2-C13
 2.6 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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 7.771
_oxdiff_exptl_absorpt_empirical_full_min 0.238
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
O1 O 0.99774(18) 0.99380(16) 0.36451(15) 0.0452(5) Uani 1 1 d D . . . .
N1 N 0.7385(2) 0.56147(16) 0.30581(15) 0.0350(5) Uani 1 1 d . . . . .
N2 N 0.92004(19) 0.89575(17) 0.41165(16) 0.0365(5) Uani 1 1 d D . . . .
C1 C 0.3986(3) 0.8025(2) 0.06480(19) 0.0400(6) Uani 1 1 d . . . . .
C2 C 0.4705(3) 0.8196(2) -0.0115(2) 0.0516(7) Uani 1 1 d . . . . .
H2 H 0.563083 0.804057 0.009234 0.062 Uiso 1 1 calc R U . . .
C3 C 0.4080(4) 0.8590(3) -0.1169(2) 0.0684(9) Uani 1 1 d . . . . .
H3 H 0.458409 0.871243 -0.168022 0.082 Uiso 1 1 calc R U . . .
C4 C 0.2752(4) 0.8804(3) -0.1483(3) 0.0777(11) Uani 1 1 d . . . . .
H4 H 0.233215 0.907955 -0.221036 0.093 Uiso 1 1 calc R U . . .
C5 C 0.2019(4) 0.8624(3) -0.0755(3) 0.0809(11) Uani 1 1 d . . . . .
H5 H 0.108300 0.875950 -0.098237 0.097 Uiso 1 1 calc R U . . .
C6 C 0.2637(3) 0.8242(3) 0.0323(2) 0.0611(8) Uani 1 1 d . . . . .
H6 H 0.212869 0.813267 0.083090 0.073 Uiso 1 1 calc R U . . .
C7 C 0.4671(2) 0.7662(2) 0.1744(2) 0.0372(6) Uani 1 1 d . . . . .
C8 C 0.5313(2) 0.7412(2) 0.2680(2) 0.0342(5) Uani 1 1 d . . . . .
C9 C 0.6189(2) 0.71224(19) 0.37383(18) 0.0312(5) Uani 1 1 d . . . . .
C10 C 0.6045(2) 0.7210(2) 0.47624(18) 0.0314(5) Uani 1 1 d . . . . .
C11 C 0.7256(2) 0.6838(2) 0.56104(18) 0.0327(5) Uani 1 1 d . . . . .
C12 C 0.8172(2) 0.6561(2) 0.50881(18) 0.0317(5) Uani 1 1 d . . . . .
C13 C 0.7585(2) 0.6751(2) 0.38454(18) 0.0313(5) Uani 1 1 d D . . . .
C14 C 0.8546(2) 0.7888(2) 0.34532(18) 0.0319(5) Uani 1 1 d . . . . .
C15 C 0.8462(2) 0.7436(2) 0.23343(19) 0.0352(6) Uani 1 1 d . . . . .
C16 C 0.7703(2) 0.6086(2) 0.2126(2) 0.0365(6) Uani 1 1 d . . . . .
C17 C 0.7386(3) 0.5372(3) 0.1100(2) 0.0480(7) Uani 1 1 d . . . . .
H17 H 0.685539 0.446204 0.094890 0.058 Uiso 1 1 calc R U . . .
C18 C 0.7870(3) 0.6034(3) 0.0309(2) 0.0604(8) Uani 1 1 d . . . . .
H18 H 0.765330 0.556941 -0.040270 0.072 Uiso 1 1 calc R U . . .
C19 C 0.8660(3) 0.7353(3) 0.0519(2) 0.0615(8) Uani 1 1 d . . . . .
H19 H 0.899084 0.776924 -0.004170 0.074 Uiso 1 1 calc R U . . .
C20 C 0.8974(3) 0.8076(3) 0.1540(2) 0.0480(7) Uani 1 1 d . . . . .
H20 H 0.952330 0.897990 0.169056 0.058 Uiso 1 1 calc R U . . .
C21 C 0.6259(3) 0.4423(2) 0.2956(2) 0.0478(7) Uani 1 1 d . . . . .
H21A H 0.533806 0.454805 0.245488 0.072 Uiso 1 1 calc R U . . .
H21B H 0.620980 0.424651 0.370328 0.072 Uiso 1 1 calc R U . . .
H21C H 0.646426 0.366418 0.263952 0.072 Uiso 1 1 calc R U . . .
C22 C 0.9399(2) 0.6197(2) 0.5692(2) 0.0403(6) Uani 1 1 d . . . . .
H22 H 1.002591 0.603314 0.533269 0.048 Uiso 1 1 calc R U . . .
C23 C 0.9706(3) 0.6072(2) 0.6841(2) 0.0470(6) Uani 1 1 d . . . . .
H23 H 1.054906 0.581742 0.727108 0.056 Uiso 1 1 calc R U . . .
C24 C 0.8797(3) 0.6313(2) 0.7361(2) 0.0469(6) Uani 1 1 d . . . . .
H24 H 0.901377 0.620535 0.814316 0.056 Uiso 1 1 calc R U . . .
C25 C 0.7568(3) 0.6713(2) 0.6760(2) 0.0405(6) Uani 1 1 d . . . . .
H25 H 0.695683 0.689587 0.712629 0.049 Uiso 1 1 calc R U . . .
C26 C 0.4912(2) 0.7667(2) 0.49918(18) 0.0332(5) Uani 1 1 d . . . . .
C27 C 0.5269(3) 0.8642(2) 0.5877(2) 0.0403(6) Uani 1 1 d . . . . .
H27 H 0.624126 0.896784 0.636416 0.048 Uiso 1 1 calc R U . . .
C28 C 0.4219(3) 0.9136(2) 0.6049(2) 0.0507(7) Uani 1 1 d . . . . .
H28 H 0.447411 0.981330 0.664476 0.061 Uiso 1 1 calc R U . . .
C29 C 0.2803(3) 0.8656(3) 0.5364(3) 0.0589(8) Uani 1 1 d . . . . .
H29 H 0.208348 0.898958 0.549548 0.071 Uiso 1 1 calc R U . . .
C30 C 0.2430(3) 0.7691(3) 0.4488(2) 0.0558(7) Uani 1 1 d . . . . .
H30 H 0.145374 0.736320 0.401101 0.067 Uiso 1 1 calc R U . . .
C31 C 0.3482(3) 0.7199(2) 0.4302(2) 0.0426(6) Uani 1 1 d . . . . .
H31 H 0.322019 0.653402 0.369604 0.051 Uiso 1 1 calc R U . . .
H1 H 1.050(3) 1.045(3) 0.4228(18) 0.086(11) Uiso 1 1 d D . . . .
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'
O O 0.0106 0.0060 '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
N2 O1 H1 100(2) . . ?
C16 N1 C13 109.33(16) . . ?
C16 N1 C21 121.67(18) . . ?
C21 N1 C13 118.83(17) . . ?
C14 N2 O1 112.66(18) . . ?
C2 C1 C7 119.3(2) . . ?
C6 C1 C2 118.7(2) . . ?
C6 C1 C7 121.9(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.9(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C1 176.5(2) . . ?
C7 C8 C9 173.9(2) . . ?
C8 C9 C13 119.64(18) . . ?
C10 C9 C8 129.2(2) . . ?
C10 C9 C13 111.01(19) . . ?
C9 C10 C11 108.42(19) . . ?
C9 C10 C26 125.7(2) . . ?
C26 C10 C11 125.81(19) . . ?
C12 C11 C10 109.31(18) . . ?
C25 C11 C10 130.9(2) . . ?
C25 C11 C12 119.8(2) . . ?
C11 C12 C13 109.34(19) . . ?
C22 C12 C11 121.4(2) . . ?
C22 C12 C13 129.2(2) . . ?
N1 C13 C9 113.90(17) . . ?
N1 C13 C12 116.02(17) . . ?
N1 C13 C14 101.50(16) . . ?
C9 C13 C14 109.09(17) . . ?
C12 C13 C9 101.82(16) . . ?
C12 C13 C14 114.81(17) . . ?
N2 C14 C13 117.95(19) . . ?
N2 C14 C15 134.7(2) . . ?
C15 C14 C13 107.34(17) . . ?
C16 C15 C14 106.67(18) . . ?
C20 C15 C14 132.6(2) . . ?
C20 C15 C16 120.8(2) . . ?
N1 C16 C15 111.59(19) . . ?
C17 C16 N1 127.5(2) . . ?
C17 C16 C15 120.9(2) . . ?
C16 C17 H17 121.3 . . ?
C18 C17 C16 117.5(2) . . ?
C18 C17 H17 121.3 . . ?
C17 C18 H18 118.9 . . ?
C17 C18 C19 122.1(2) . . ?
C19 C18 H18 118.9 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.7(2) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 117.9(2) . . ?
C15 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C22 H22 120.7 . . ?
C12 C22 C23 118.5(2) . . ?
C23 C22 H22 120.7 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.1(2) . . ?
C25 C24 H24 119.4 . . ?
C11 C25 C24 118.5(2) . . ?
C11 C25 H25 120.8 . . ?
C24 C25 H25 120.8 . . ?
C27 C26 C10 120.2(2) . . ?
C31 C26 C10 121.17(19) . . ?
C31 C26 C27 118.6(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(2) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.5(2) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.0(2) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.9(3) . . ?
C31 C30 H30 120.1 . . ?
C26 C31 C30 120.8(2) . . ?
C26 C31 H31 119.6 . . ?
C30 C31 H31 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
O1 N2 1.401(2) . ?
O1 H1 0.839(10) . ?
N1 C13 1.470(3) . ?
N1 C16 1.388(3) . ?
N1 C21 1.444(3) . ?
N2 C14 1.278(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.377(4) . ?
C1 C7 1.421(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.357(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.364(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.205(3) . ?
C8 C9 1.414(3) . ?
C9 C10 1.360(3) . ?
C9 C13 1.535(3) . ?
C10 C11 1.471(3) . ?
C10 C26 1.470(3) . ?
C11 C12 1.401(3) . ?
C11 C25 1.392(3) . ?
C12 C13 1.511(3) . ?
C12 C22 1.373(3) . ?
C13 C14 1.545(3) . ?
C14 C15 1.458(3) . ?
C15 C16 1.401(3) . ?
C15 C20 1.388(3) . ?
C16 C17 1.389(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C23 1.392(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.392(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.395(3) . ?
C26 C31 1.387(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.380(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.376(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.376(4) . ?
C30 H30 0.9500 . ?
C30 C31 1.387(4) . ?
C31 H31 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
O1 N2 C14 C13 -176.91(18) . . . . ?
O1 N2 C14 C15 2.5(4) . . . . ?
N1 C13 C14 N2 -164.28(19) . . . . ?
N1 C13 C14 C15 16.1(2) . . . . ?
N1 C16 C17 C18 -176.9(2) . . . . ?
N2 C14 C15 C16 172.5(2) . . . . ?
N2 C14 C15 C20 -7.0(5) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C7 C1 C2 C3 -177.9(2) . . . . ?
C7 C1 C6 C5 178.7(2) . . . . ?
C8 C9 C10 C11 -178.27(19) . . . . ?
C8 C9 C10 C26 -1.2(3) . . . . ?
C8 C9 C13 N1 -55.5(2) . . . . ?
C8 C9 C13 C12 178.80(17) . . . . ?
C8 C9 C13 C14 57.1(2) . . . . ?
C9 C10 C11 C12 1.9(2) . . . . ?
C9 C10 C11 C25 -176.9(2) . . . . ?
C9 C10 C26 C27 -129.8(2) . . . . ?
C9 C10 C26 C31 46.6(3) . . . . ?
C9 C13 C14 N2 75.2(2) . . . . ?
C9 C13 C14 C15 -104.39(19) . . . . ?
C10 C9 C13 N1 128.89(19) . . . . ?
C10 C9 C13 C12 3.2(2) . . . . ?
C10 C9 C13 C14 -118.5(2) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C10 C11 C12 C22 179.49(18) . . . . ?
C10 C11 C25 C24 178.8(2) . . . . ?
C10 C26 C27 C28 175.7(2) . . . . ?
C10 C26 C31 C30 -176.3(2) . . . . ?
C11 C10 C26 C27 46.8(3) . . . . ?
C11 C10 C26 C31 -136.8(2) . . . . ?
C11 C12 C13 N1 -126.22(19) . . . . ?
C11 C12 C13 C9 -2.0(2) . . . . ?
C11 C12 C13 C14 115.7(2) . . . . ?
C11 C12 C22 C23 1.6(3) . . . . ?
C12 C11 C25 C24 0.1(3) . . . . ?
C12 C13 C14 N2 -38.3(3) . . . . ?
C12 C13 C14 C15 142.11(19) . . . . ?
C12 C22 C23 C24 -0.2(3) . . . . ?
C13 N1 C16 C15 15.5(3) . . . . ?
C13 N1 C16 C17 -166.1(2) . . . . ?
C13 C9 C10 C11 -3.2(2) . . . . ?
C13 C9 C10 C26 173.87(18) . . . . ?
C13 C12 C22 C23 -179.30(19) . . . . ?
C13 C14 C15 C16 -8.0(2) . . . . ?
C13 C14 C15 C20 172.5(3) . . . . ?
C14 C15 C16 N1 -4.3(3) . . . . ?
C14 C15 C16 C17 177.3(2) . . . . ?
C14 C15 C20 C19 -177.9(3) . . . . ?
C15 C16 C17 C18 1.3(4) . . . . ?
C16 N1 C13 C9 98.2(2) . . . . ?
C16 N1 C13 C12 -144.08(19) . . . . ?
C16 N1 C13 C14 -18.9(2) . . . . ?
C16 C15 C20 C19 2.7(4) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
C17 C18 C19 C20 -1.3(5) . . . . ?
C18 C19 C20 C15 -0.5(4) . . . . ?
C20 C15 C16 N1 175.3(2) . . . . ?
C20 C15 C16 C17 -3.1(4) . . . . ?
C21 N1 C13 C9 -47.8(3) . . . . ?
C21 N1 C13 C12 70.0(3) . . . . ?
C21 N1 C13 C14 -164.84(19) . . . . ?
C21 N1 C16 C15 160.3(2) . . . . ?
C21 N1 C16 C17 -21.4(4) . . . . ?
C22 C12 C13 N1 54.6(3) . . . . ?
C22 C12 C13 C9 178.9(2) . . . . ?
C22 C12 C13 C14 -63.4(3) . . . . ?
C22 C23 C24 C25 -1.3(4) . . . . ?
C23 C24 C25 C11 1.3(3) . . . . ?
C25 C11 C12 C13 179.19(18) . . . . ?
C25 C11 C12 C22 -1.6(3) . . . . ?
C26 C10 C11 C12 -175.20(19) . . . . ?
C26 C10 C11 C25 6.0(4) . . . . ?
C26 C27 C28 C29 1.2(4) . . . . ?
C27 C26 C31 C30 0.1(3) . . . . ?
C27 C28 C29 C30 -1.1(4) . . . . ?
C28 C29 C30 C31 0.4(4) . . . . ?
C29 C30 C31 C26 0.1(4) . . . . ?
C31 C26 C27 C28 -0.7(3) . . . . ?
