#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:59:33 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272753 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158483.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_7158483
loop_
_publ_author_name
'Xu, Lichun'
'Ma, Zhongxiao'
'Hu, Xi'
'Zhang, Xin'
'Gao, Shulin'
'Liang, Deqiang'
'Wang, Baoling'
'Li, Weili'
'Li, Yanni'
_publ_section_title
;
 Electroreductive synthesis of polyfunctionalized pyridin-2-ones from
 acetoacetanilides and carbon disulfide with oxygen evolution.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1013
_journal_page_last               1018
_journal_paper_doi               10.1039/d1ob02379a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C21 H18 N2 O3'
_chemical_formula_sum            'C21 H18 N2 O3'
_chemical_formula_weight         346.37
_chemical_name_systematic
5-acetyl-2-methyl-6-oxo-N,1-diphenyl-1,6-dihydropyridine-3-carboxamide
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-09-11
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2021-10-07 deposited with the CCDC.	2022-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                92.542(8)
_cell_angle_beta                 98.729(10)
_cell_angle_gamma                97.055(9)
_cell_formula_units_Z            2
_cell_length_a                   8.1439(10)
_cell_length_b                   9.6588(8)
_cell_length_c                   11.5840(13)
_cell_measurement_reflns_used    2034
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5730
_cell_measurement_theta_min      3.8780
_cell_volume                     891.98(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9925
_diffrn_measured_fraction_theta_max 0.9731
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 -43.00   1.00    1.00    --    0.00 -57.00 -90.00   26
  2  ω    -30.00  -4.00   1.00    1.00    --    0.00 -57.00 -90.00   26
  3  ω     -8.00  21.00   1.00    1.00    --    0.00  57.00  30.00   29
  4  ω     39.00  66.00   1.00    1.00    --    0.00  57.00  30.00   27
  5  ω    -16.00  11.00   1.00    1.00    --   54.00 -19.00 -60.00   27
  6  ω      1.00  74.00   1.00    1.00    --   54.00 -57.00 -60.00   73
  7  ω     30.00 126.00   1.00    1.00    --   54.00  37.00 120.00   96
  8  ω     41.00 106.00   1.00    1.00    --   54.00-125.00 150.00   65
  9  ω     16.00  67.00   1.00    1.00    --   54.00 -19.00 -60.00   51
 10  ω     -5.00  39.00   1.00    1.00    --   54.00 -57.00 150.00   44
 11  ω    -10.00  71.00   1.00    1.00    --   54.00 -57.00-150.00   81
 12  ω     66.00 105.00   1.00    1.00    --  108.00-111.00-120.00   39
 13  ω     86.00 175.00   1.00    1.00    --  108.00  37.00   0.00   89
 14  ω    103.00 174.00   1.00    1.00    --  108.00 111.00-180.00   71
 15  ω     65.00 100.00   1.00    1.00    --  108.00 -25.00  90.00   35
 16  ω     73.00 103.00   1.00    1.00    --  108.00-111.00 -30.00   30
 17  ω     88.00 168.00   1.00    1.00    --  108.00  50.00-120.00   80
 18  ω    142.00 172.00   1.00    1.00    --  108.00  50.00 -90.00   30
 19  ω     90.00 124.00   1.00    1.00    --  108.00  50.00 -90.00   34
 20  ω     40.00 126.00   1.00    1.00    --  108.00 -63.00-150.00   86
 21  ω     92.00 173.00   1.00    1.00    --  108.00  50.00 -60.00   81
 22  ω     44.00 108.00   1.00    1.00    --  108.00-111.00  30.00   64
 23  ω     65.00 112.00   1.00    1.00    --  108.00-111.00 120.00   47
 24  ω     37.00  63.00   1.00    1.00    --  108.00-111.00 120.00   26
 25  ω     71.00 116.00   1.00    1.00    --  108.00 178.00 120.00   45
 26  ω     40.00 130.00   1.00    1.00    --  108.00 -63.00  90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0993267000
_diffrn_orient_matrix_UB_12      0.1158295000
_diffrn_orient_matrix_UB_13      0.0880988000
_diffrn_orient_matrix_UB_21      0.1406800000
_diffrn_orient_matrix_UB_22      0.0159053000
_diffrn_orient_matrix_UB_23      -0.0754755000
_diffrn_orient_matrix_UB_31      -0.0872524000
_diffrn_orient_matrix_UB_32      0.1107549000
_diffrn_orient_matrix_UB_33      -0.0687062000
_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  0.0166
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5461
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.87
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0069(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0635P)²+0.1338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                2613
_reflns_number_total             3166
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob02379a2.cif
_cod_data_source_block           exp_3536
_cod_depositor_comments          'Adding full bibliography for 7158483.cif.'
_cod_database_code               7158483
_reflns_odcompleteness_completeness 99.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Riding coordinates:
 C14(H1A)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.791
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0591(2) 0.11040(17) -0.19108(15) 0.0548(4) Uani 1 1 d . . .
H1 H -0.0223 0.1344 -0.1484 0.066 Uiso 1 1 calc R . .
C2 C 0.0178(3) 0.0115(2) -0.28517(18) 0.0684(5) Uani 1 1 d . . .
H2 H -0.0922 -0.0312 -0.3056 0.082 Uiso 1 1 calc R . .
C3 C 0.1377(3) -0.0233(2) -0.34790(18) 0.0754(6) Uani 1 1 d . . .
H3 H 0.1091 -0.0894 -0.4109 0.091 Uiso 1 1 calc R . .
C4 C 0.3000(3) 0.0391(2) -0.31793(19) 0.0810(7) Uani 1 1 d . . .
H4 H 0.3813 0.0150 -0.3606 0.097 Uiso 1 1 calc R . .
C5 C 0.3435(2) 0.1382(2) -0.22428(17) 0.0660(5) Uani 1 1 d . . .
H5 H 0.4535 0.1810 -0.2040 0.079 Uiso 1 1 calc R . .
C6 C 0.2221(2) 0.17201(15) -0.16218(13) 0.0453(4) Uani 1 1 d . . .
C7 C 0.3263(3) 0.08571(17) 0.06218(16) 0.0651(5) Uani 1 1 d . . .
H7A H 0.2155 0.0371 0.0595 0.098 Uiso 1 1 calc R . .
H7B H 0.3928 0.0744 0.1362 0.098 Uiso 1 1 calc R . .
H7C H 0.3769 0.0480 0.0002 0.098 Uiso 1 1 calc R . .
C8 C 0.31648(19) 0.23779(15) 0.04766(13) 0.0441(4) Uani 1 1 d . . .
C9 C 0.35636(19) 0.33930(16) 0.13842(13) 0.0439(4) Uani 1 1 d . . .
C10 C 0.33396(19) 0.47762(16) 0.11479(13) 0.0439(4) Uani 1 1 d . . .
H10 H 0.3589 0.5458 0.1763 0.053 Uiso 1 1 calc R . .
C11 C 0.27712(19) 0.51673(15) 0.00538(13) 0.0426(4) Uani 1 1 d . . .
C12 C 0.25396(18) 0.41617(15) -0.09282(13) 0.0424(4) Uani 1 1 d . . .
C13 C 0.2390(2) 0.66294(16) -0.00792(15) 0.0507(4) Uani 1 1 d . . .
C14 C 0.1414(3) 0.7030(2) -0.11855(19) 0.0767(6) Uani 1 1 d . . .
H14A H 0.1093 0.7942 -0.1062 0.115 Uiso 1 1 calc R . .
H14B H 0.0428 0.6363 -0.1410 0.115 Uiso 1 1 calc R . .
H14C H 0.2094 0.7042 -0.1794 0.115 Uiso 1 1 calc R . .
H1A H 0.5939 0.4629 0.2750 0.092 Uiso 1 1 d R . .
C15 C 0.4118(2) 0.30203(17) 0.26157(14) 0.0489(4) Uani 1 1 d . . .
C16 C 0.6279(2) 0.38277(19) 0.43565(13) 0.0506(4) Uani 1 1 d . . .
C17 C 0.6027(3) 0.2697(2) 0.50285(15) 0.0633(5) Uani 1 1 d . . .
H17 H 0.5196 0.1954 0.4762 0.076 Uiso 1 1 calc R . .
C18 C 0.7034(3) 0.2688(3) 0.61073(16) 0.0751(6) Uani 1 1 d . . .
H18 H 0.6877 0.1924 0.6559 0.090 Uiso 1 1 calc R . .
C19 C 0.8243(3) 0.3767(3) 0.65204(16) 0.0790(7) Uani 1 1 d . . .
H19 H 0.8924 0.3731 0.7237 0.095 Uiso 1 1 calc R . .
C20 C 0.8448(3) 0.4912(3) 0.58678(18) 0.0804(7) Uani 1 1 d . . .
H20 H 0.9249 0.5668 0.6155 0.097 Uiso 1 1 calc R . .
C21 C 0.7469(2) 0.4947(2) 0.47841(16) 0.0675(5) Uani 1 1 d . . .
H21 H 0.7614 0.5723 0.4346 0.081 Uiso 1 1 calc R . .
N1 N 0.54109(18) 0.39051(14) 0.32028(11) 0.0517(4) Uani 1 1 d . . .
N2 N 0.26563(16) 0.27608(12) -0.06358(10) 0.0421(3) Uani 1 1 d . . .
O1 O 0.34416(18) 0.19999(14) 0.30272(11) 0.0736(4) Uani 1 1 d . . .
O2 O 0.22626(16) 0.43930(11) -0.19683(9) 0.0557(3) Uani 1 1 d . . .
O3 O 0.2809(2) 0.74853(13) 0.07472(12) 0.0800(5) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C6 C1 C2 118.86(18) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.47(18) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.97(18) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 118.99(18) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 N2 118.95(15) . . ?
C5 C6 C1 121.33(15) . . ?
C5 C6 N2 119.72(14) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
C9 C8 C7 123.84(14) . . ?
N2 C8 C7 116.96(14) . . ?
N2 C8 C9 119.19(13) . . ?
C8 C9 C10 118.53(13) . . ?
C8 C9 C15 120.98(13) . . ?
C10 C9 C15 120.37(14) . . ?
C9 C10 H10 118.5 . . ?
C11 C10 C9 123.01(14) . . ?
C11 C10 H10 118.5 . . ?
C10 C11 C12 119.37(13) . . ?
C10 C11 C13 118.65(14) . . ?
C12 C11 C13 121.97(13) . . ?
N2 C12 C11 115.03(13) . . ?
O2 C12 C11 126.96(14) . . ?
O2 C12 N2 118.01(13) . . ?
C11 C13 C14 120.96(15) . . ?
O3 C13 C11 119.21(15) . . ?
O3 C13 C14 119.73(16) . . ?
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 . . ?
N1 C15 C9 113.89(13) . . ?
O1 C15 C9 122.03(14) . . ?
O1 C15 N1 124.07(15) . . ?
C17 C16 N1 123.84(16) . . ?
C21 C16 C17 119.86(16) . . ?
C21 C16 N1 116.27(16) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.89(19) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.6(2) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.26(18) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 119.9(2) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C15 N1 H1A 116.6 . . ?
C15 N1 C16 128.38(14) . . ?
C16 N1 H1A 114.4 . . ?
C8 N2 C6 121.00(12) . . ?
C8 N2 C12 124.05(12) . . ?
C12 N2 C6 114.94(12) . . ?
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
C1 H1 0.9300 . ?
C1 C2 1.389(2) . ?
C1 C6 1.371(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(3) . ?
C6 N2 1.4589(19) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 C8 1.496(2) . ?
C8 C9 1.378(2) . ?
C8 N2 1.3735(19) . ?
C9 C10 1.404(2) . ?
C9 C15 1.503(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.368(2) . ?
C11 C12 1.437(2) . ?
C11 C13 1.492(2) . ?
C12 N2 1.4203(19) . ?
C12 O2 1.2273(18) . ?
C13 C14 1.495(2) . ?
C13 O3 1.216(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N1 1.346(2) . ?
C15 O1 1.221(2) . ?
C16 C17 1.382(3) . ?
C16 C21 1.379(3) . ?
C16 N1 1.4235(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.358(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.375(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(3) . ?
C21 H21 0.9300 . ?
N1 H1A 0.9880 . ?
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
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C6 N2 C8 90.50(19) . . . . ?
C1 C6 N2 C12 -90.61(17) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C1 C6 N2 179.86(15) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 N2 -179.92(18) . . . . ?
C5 C6 N2 C8 -89.8(2) . . . . ?
C5 C6 N2 C12 89.06(19) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C7 C8 C9 C10 -176.81(16) . . . . ?
C7 C8 C9 C15 -0.8(2) . . . . ?
C7 C8 N2 C6 0.5(2) . . . . ?
C7 C8 N2 C12 -178.25(15) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
C8 C9 C15 N1 137.76(16) . . . . ?
C8 C9 C15 O1 -42.0(2) . . . . ?
C9 C8 N2 C6 -179.94(14) . . . . ?
C9 C8 N2 C12 1.3(2) . . . . ?
C9 C10 C11 C12 -6.2(2) . . . . ?
C9 C10 C11 C13 173.04(14) . . . . ?
C9 C15 N1 C16 -177.24(15) . . . . ?
C10 C9 C15 N1 -46.3(2) . . . . ?
C10 C9 C15 O1 133.89(19) . . . . ?
C10 C11 C12 N2 10.4(2) . . . . ?
C10 C11 C12 O2 -169.35(16) . . . . ?
C10 C11 C13 C14 -166.07(18) . . . . ?
C10 C11 C13 O3 10.2(3) . . . . ?
C11 C12 N2 C6 172.87(13) . . . . ?
C11 C12 N2 C8 -8.3(2) . . . . ?
C12 C11 C13 C14 13.2(3) . . . . ?
C12 C11 C13 O3 -170.57(16) . . . . ?
C13 C11 C12 N2 -168.82(13) . . . . ?
C13 C11 C12 O2 11.4(3) . . . . ?
C15 C9 C10 C11 -177.21(14) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C17 C16 C21 C20 2.3(3) . . . . ?
C17 C16 N1 C15 7.7(3) . . . . ?
C17 C18 C19 C20 1.6(3) . . . . ?
C18 C19 C20 C21 -2.0(3) . . . . ?
C19 C20 C21 C16 0.1(3) . . . . ?
C21 C16 C17 C18 -2.7(3) . . . . ?
C21 C16 N1 C15 -174.46(18) . . . . ?
N1 C16 C17 C18 175.10(17) . . . . ?
N1 C16 C21 C20 -175.65(17) . . . . ?
N2 C8 C9 C10 3.7(2) . . . . ?
N2 C8 C9 C15 179.72(14) . . . . ?
O1 C15 N1 C16 2.6(3) . . . . ?
O2 C12 N2 C6 -7.3(2) . . . . ?
O2 C12 N2 C8 171.52(14) . . . . ?
