#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:28:30 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268934 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/82/7158232.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_7158232
loop_
_publ_author_name
'Pradhan, Subham'
'Thiyagarajan, Subramanian'
'Gunanathan, Chidambaram'
_publ_section_title
;
 Ruthenium(ii)-catalysed 1,2-selective hydroboration of aldazines.
;
_journal_issue                   33
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7147
_journal_page_last               7151
_journal_paper_doi               10.1039/d1ob01218e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C18 H22 N2 O2'
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.37
_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
_audit_creation_date             2021-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2021-04-14 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                80.613(3)
_cell_angle_beta                 85.440(3)
_cell_angle_gamma                89.520(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2951(2)
_cell_length_b                   7.8493(3)
_cell_length_c                   16.3441(5)
_cell_measurement_reflns_used    7407
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.1210
_cell_measurement_theta_min      5.4840
_cell_volume                     794.25(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00 -14.00   0.50    0.88    --  -38.50 141.00-114.00  170
  2  ω    -90.00  -8.00   0.50    0.88    --  -38.50 129.00  73.00  164
  3  ω     36.00 110.00   0.50    0.88    --   49.31-141.00-172.00  148
  4  ω     30.00 103.00   0.50    0.88    --   49.31-129.00  -0.00  146
  5  ω     39.00 115.00   0.50    3.49    --  102.63-129.00  -0.00  152
  6  ω     95.00 167.00   0.50    3.49    --  102.63 129.00  73.00  144
  7  ω     39.00 124.00   0.50    3.49    --  102.63-141.00-172.00  170
  8  ω     88.00 166.00   0.50    3.49    --  102.63 141.00-114.00  156
  9  ω   -105.00 -35.00   0.50    0.88    --  -38.50 -38.00   0.00  140
 10  ω   -105.00 -35.00   0.50    0.88    --  -38.50 -38.00-180.00  140
 11  ω    -42.00  28.00   0.50    0.88    --  -38.50  38.00-180.00  140
 12  ω    -42.00  28.00   0.50    0.88    --  -38.50  38.00 -60.00  140
 13  ω     40.00 116.00   0.50    3.49    --  102.63 -61.00 150.00  152
 14  ω     99.00 171.00   0.50    3.49    --  102.63  30.00 -90.00  144
 15  ω     38.00 107.00   0.50    3.49    --  102.63 -45.00 -30.00  138
 16  ω    103.00 167.00   0.50    3.49    --  102.63  77.00 -30.00  128
 17  ω     38.00 107.00   0.50    3.49    --  102.63 -45.00-180.00  138
 18  ω     35.00 106.00   0.50    3.49    --  102.63 -30.00 120.00  142
 19  ω     98.00 167.00   0.50    3.49    --  102.63  45.00  90.00  138
 20  ω     34.00 107.00   0.50    3.49    --  102.63 -94.00 150.00  146
 21  ω     38.00 126.00   0.50    3.49    --  102.63 -77.00 -30.00  176
 22  ω     95.00 171.00   0.50    3.49    --  102.63  15.00-180.00  152
 23  ω     38.00 107.00   0.50    3.49    --  102.63 -45.00-120.00  138
 24  ω     40.00 116.00   0.50    3.49    --  102.63 -61.00   0.00  152
 25  ω     38.00 112.00   0.50    3.49    --  102.63-125.00 -90.00  148
 26  ω     34.00 107.00   0.50    3.49    --  102.63 -94.00 -30.00  146
 27  ω     90.00 165.00   0.50    3.49    --  102.63  61.00 150.00  150
 28  ω    103.00 167.00   0.50    3.49    --  102.63  77.00-120.00  128
 29  ω     38.00 112.00   0.50    3.49    --  102.63-125.00 120.00  148
 30  ω     99.00 171.00   0.50    3.49    --  102.63  30.00  30.00  144
 31  ω   -101.00 -27.00   0.50    0.88    --  -38.50 -57.00 -90.00  148
 32  ω     38.00 112.00   0.50    0.88    --   49.31  57.00 120.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1437773000
_diffrn_orient_matrix_UB_12      -0.0233417000
_diffrn_orient_matrix_UB_13      -0.0781336000
_diffrn_orient_matrix_UB_21      -0.1601905000
_diffrn_orient_matrix_UB_22      0.1022336000
_diffrn_orient_matrix_UB_23      -0.0553316000
_diffrn_orient_matrix_UB_31      0.1180669000
_diffrn_orient_matrix_UB_32      0.1690570000
_diffrn_orient_matrix_UB_33      0.0042933000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12051
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.831
_diffrn_reflns_theta_min         5.504
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0020(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0752P)²+0.1820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2845
_reflns_number_total             3191
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01218e2.cif
_cod_data_source_block           cg-sp-96
_cod_depositor_comments
'Adding full bibliography for 7158232--7158234.cif.'
_cod_database_code               7158232
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C38 H46 N2 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.
;
_diffrn_oxdiff_digest_frames
;
0199e80f5b6b5c2dcd3f935e022fa7c17b00033e592
;
_diffrn_oxdiff_digest_hkl
;
018773a3b8a7fda95d06f2129fb964651562f5
;
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C7(H7A,H7B), C21(H21A,H21B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C15(H15), C10(H10), C12(H12), C16(H16), C5(H5), C13(H13), C3(H3),
 C6(H6), C2(H2)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C22(H22A,H22B,H22C)
;
_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 3.276
_oxdiff_exptl_absorpt_empirical_full_min 0.645
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
O17 O 0.21608(14) 0.62020(12) 0.05787(5) 0.0303(2) Uani 1 1 d . . . . .
O20 O 1.20560(14) 0.03516(12) 0.78753(5) 0.0313(2) Uani 1 1 d . . . . .
N9 N 0.52463(17) 0.38079(14) 0.42410(6) 0.0292(3) Uani 1 1 d . . . . .
N8 N 0.62132(18) 0.30697(15) 0.49281(7) 0.0322(3) Uani 1 1 d . . . . .
H8 H 0.570736 0.323838 0.541272 0.039 Uiso 1 1 calc R . . . .
C14 C 0.2870(2) 0.54891(16) 0.13299(8) 0.0273(3) Uani 1 1 d . . . . .
C4 C 1.11576(19) 0.08272(16) 0.71371(7) 0.0270(3) Uani 1 1 d . . . . .
C15 C 0.4756(2) 0.45480(16) 0.12899(8) 0.0290(3) Uani 1 1 d . . . . .
H15 H 0.542343 0.440937 0.077669 0.035 Uiso 1 1 calc R . . . .
C1 C 0.9111(2) 0.16151(17) 0.56604(8) 0.0300(3) Uani 1 1 d . . . . .
C10 C 0.57295(19) 0.32972(16) 0.35411(8) 0.0281(3) Uani 1 1 d . . . . .
H10 H 0.676309 0.245249 0.350775 0.034 Uiso 1 1 calc R . . . .
C12 C 0.2761(2) 0.49416(17) 0.28235(8) 0.0303(3) Uani 1 1 d . . . . .
H12 H 0.208363 0.506900 0.333654 0.036 Uiso 1 1 calc R . . . .
C16 C 0.5627(2) 0.38230(16) 0.20154(8) 0.0291(3) Uani 1 1 d . . . . .
H16 H 0.687429 0.318543 0.198391 0.035 Uiso 1 1 calc R . . . .
C5 C 0.9368(2) -0.01138(17) 0.70196(8) 0.0305(3) Uani 1 1 d . . . . .
H5 H 0.885101 -0.100670 0.743120 0.037 Uiso 1 1 calc R . . . .
C13 C 0.1854(2) 0.56621(17) 0.21018(8) 0.0305(3) Uani 1 1 d . . . . .
H13 H 0.057458 0.625781 0.213213 0.037 Uiso 1 1 calc R . . . .
C11 C 0.4676(2) 0.40263(16) 0.27956(8) 0.0273(3) Uani 1 1 d . . . . .
C3 C 1.1920(2) 0.21605(17) 0.65174(8) 0.0310(3) Uani 1 1 d . . . . .
H3 H 1.311187 0.279507 0.659011 0.037 Uiso 1 1 calc R . . . .
C6 C 0.8363(2) 0.02824(17) 0.62901(8) 0.0315(3) Uani 1 1 d . . . . .
H6 H 0.716801 -0.034890 0.621730 0.038 Uiso 1 1 calc R . . . .
C2 C 1.0887(2) 0.25375(17) 0.57884(8) 0.0323(3) Uani 1 1 d . . . . .
H2 H 1.140120 0.343117 0.537669 0.039 Uiso 1 1 calc R . . . .
C7 C 0.8085(2) 0.20038(18) 0.48501(8) 0.0331(3) Uani 1 1 d . . . . .
H7A H 0.910073 0.259625 0.442299 0.040 Uiso 1 1 calc R . . . .
H7B H 0.768250 0.093051 0.468093 0.040 Uiso 1 1 calc R . . . .
C21 C 1.4026(2) 0.11869(17) 0.79738(9) 0.0336(3) Uani 1 1 d . . . . .
H21A H 1.379493 0.241238 0.796700 0.040 Uiso 1 1 calc R . . . .
H21B H 1.507045 0.104486 0.752105 0.040 Uiso 1 1 calc R . . . .
C18 C 0.0148(2) 0.70809(17) 0.05830(8) 0.0317(3) Uani 1 1 d . . . . .
H18A H 0.020165 0.804706 0.088297 0.038 Uiso 1 1 calc R . . . .
H18B H -0.097601 0.629919 0.085220 0.038 Uiso 1 1 calc R . . . .
C19 C -0.0270(2) 0.77094(18) -0.03076(9) 0.0372(3) Uani 1 1 d . . . . .
H19A H -0.024305 0.674953 -0.060472 0.056 Uiso 1 1 calc GR . . . .
H19B H 0.080942 0.853065 -0.055811 0.056 Uiso 1 1 calc GR . . . .
H19C H -0.164227 0.824959 -0.032915 0.056 Uiso 1 1 calc GR . . . .
C22 C 1.4817(2) 0.03769(19) 0.87897(10) 0.0408(4) Uani 1 1 d . . . . .
H22A H 1.494494 -0.084757 0.880616 0.061 Uiso 1 1 calc GR . . . .
H22B H 1.382714 0.060397 0.923662 0.061 Uiso 1 1 calc GR . . . .
H22C H 1.618387 0.085633 0.884810 0.061 Uiso 1 1 calc GR . . . .
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'
O O 0.0492 0.0322 '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
C14 O17 C18 117.85(10) . . ?
C4 O20 C21 117.03(10) . . ?
C10 N9 N8 119.54(10) . . ?
N9 N8 H8 119.7 . . ?
N9 N8 C7 120.64(10) . . ?
C7 N8 H8 119.7 . . ?
O17 C14 C15 115.59(11) . . ?
O17 C14 C13 124.59(11) . . ?
C13 C14 C15 119.82(11) . . ?
O20 C4 C5 116.22(11) . . ?
O20 C4 C3 124.17(11) . . ?
C3 C4 C5 119.61(12) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.76(11) . . ?
C16 C15 H15 120.1 . . ?
C6 C1 C7 121.50(12) . . ?
C2 C1 C6 118.09(12) . . ?
C2 C1 C7 120.37(12) . . ?
N9 C10 H10 119.5 . . ?
N9 C10 C11 120.99(11) . . ?
C11 C10 H10 119.5 . . ?
C13 C12 H12 119.3 . . ?
C13 C12 C11 121.33(11) . . ?
C11 C12 H12 119.3 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C11 121.48(11) . . ?
C11 C16 H16 119.3 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.95(12) . . ?
C6 C5 H5 120.0 . . ?
C14 C13 H13 120.2 . . ?
C12 C13 C14 119.67(11) . . ?
C12 C13 H13 120.2 . . ?
C12 C11 C10 123.14(11) . . ?
C16 C11 C10 118.95(11) . . ?
C16 C11 C12 117.90(11) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.53(12) . . ?
C2 C3 H3 120.2 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.18(12) . . ?
C5 C6 H6 119.4 . . ?
C1 C2 C3 121.64(12) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
N8 C7 C1 111.04(10) . . ?
N8 C7 H7A 109.4 . . ?
N8 C7 H7B 109.4 . . ?
C1 C7 H7A 109.4 . . ?
C1 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
O20 C21 H21A 110.1 . . ?
O20 C21 H21B 110.1 . . ?
O20 C21 C22 108.20(11) . . ?
H21A C21 H21B 108.4 . . ?
C22 C21 H21A 110.1 . . ?
C22 C21 H21B 110.1 . . ?
O17 C18 H18A 110.3 . . ?
O17 C18 H18B 110.3 . . ?
O17 C18 C19 107.24(11) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O17 C14 1.3707(14) . ?
O17 C18 1.4375(15) . ?
O20 C4 1.3685(14) . ?
O20 C21 1.4398(16) . ?
N9 N8 1.3630(14) . ?
N9 C10 1.2861(17) . ?
N8 H8 0.8600 . ?
N8 C7 1.4486(16) . ?
C14 C15 1.3957(17) . ?
C14 C13 1.3946(18) . ?
C4 C5 1.3951(18) . ?
C4 C3 1.3917(18) . ?
C15 H15 0.9300 . ?
C15 C16 1.3816(17) . ?
C1 C6 1.3983(19) . ?
C1 C2 1.385(2) . ?
C1 C7 1.5051(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.4651(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.3860(17) . ?
C12 C11 1.3997(17) . ?
C16 H16 0.9300 . ?
C16 C11 1.3975(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.3836(17) . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.3912(18) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.5014(18) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.5019(18) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
O17 C14 C15 C16 178.15(10) . . . . ?
O17 C14 C13 C12 -177.43(11) . . . . ?
O20 C4 C5 C6 -179.97(10) . . . . ?
O20 C4 C3 C2 179.93(11) . . . . ?
N9 N8 C7 C1 169.15(11) . . . . ?
N9 C10 C11 C12 -17.25(19) . . . . ?
N9 C10 C11 C16 161.99(12) . . . . ?
N8 N9 C10 C11 178.19(11) . . . . ?
C14 O17 C18 C19 -179.13(10) . . . . ?
C14 C15 C16 C11 -0.8(2) . . . . ?
C4 O20 C21 C22 -175.37(10) . . . . ?
C4 C5 C6 C1 0.19(19) . . . . ?
C4 C3 C2 C1 -0.11(19) . . . . ?
C15 C14 C13 C12 1.97(19) . . . . ?
C15 C16 C11 C10 -177.10(11) . . . . ?
C15 C16 C11 C12 2.18(19) . . . . ?
C10 N9 N8 C7 13.51(18) . . . . ?
C5 C4 C3 C2 0.00(18) . . . . ?
C13 C14 C15 C16 -1.31(19) . . . . ?
C13 C12 C11 C10 177.75(11) . . . . ?
C13 C12 C11 C16 -1.50(19) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.03(18) . . . . ?
C6 C1 C2 C3 0.26(19) . . . . ?
C6 C1 C7 N8 82.32(15) . . . . ?
C2 C1 C6 C5 -0.30(19) . . . . ?
C2 C1 C7 N8 -100.14(14) . . . . ?
C7 C1 C6 C5 177.30(11) . . . . ?
C7 C1 C2 C3 -177.36(11) . . . . ?
C21 O20 C4 C5 173.86(11) . . . . ?
C21 O20 C4 C3 -6.07(17) . . . . ?
C18 O17 C14 C15 175.69(11) . . . . ?
C18 O17 C14 C13 -4.88(18) . . . . ?
