#------------------------------------------------------------------------------
#$Date: 2023-11-06 10:22:42 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287418 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159572.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_7159572
loop_
_publ_author_name
'He, Heng'
'Liu, Jian-Quan'
'Wang, Xiang-Shan'
_publ_section_title
;
 Synthesis of pyrimidine-fused skeletons through copper-catalyzed
 consecutive Sonogashira coupling and aminocyclization.
;
_journal_issue                   39
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7886
_journal_page_last               7890
_journal_paper_doi               10.1039/d3ob01248d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C24 H22 N4 O2'
_chemical_formula_weight         398.45
_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_method           SHELXL-2018/3
_audit_update_record
;
2023-04-03 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                108.2800(10)
_cell_angle_beta                 93.0630(10)
_cell_angle_gamma                108.3660(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8519(9)
_cell_length_b                   9.9144(11)
_cell_length_c                   12.8442(14)
_cell_measurement_reflns_used    3880
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.41
_cell_measurement_theta_min      2.72
_cell_volume                     1001.21(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5053
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.309
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       Block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.025(4)
_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   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0415
_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)+(0.0657P)²+0.2239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3002
_reflns_number_total             3473
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01248d2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7159572--7159574.cif.'
_cod_database_code               7159572
_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. 
;
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
C24 C 0.3350(3) 0.0922(2) -0.43766(17) 0.0759(6) Uani 1 1 d . . . . .
H24A H 0.301616 -0.013347 -0.482177 0.114 Uiso 1 1 calc R U . . .
H24B H 0.342036 0.150928 -0.485304 0.114 Uiso 1 1 calc R U . . .
H24C H 0.438816 0.123036 -0.393151 0.114 Uiso 1 1 calc R U . . .
C23 C 0.2136(2) 0.1175(2) -0.36283(15) 0.0624(5) Uani 1 1 d . . . . .
H23A H 0.205346 0.055775 -0.316426 0.075 Uiso 1 1 calc R U . . .
H23B H 0.108649 0.083643 -0.408500 0.075 Uiso 1 1 calc R U . . .
C22 C 0.2553(2) 0.2817(2) -0.28855(15) 0.0572(4) Uani 1 1 d . . . . .
H22A H 0.264678 0.343886 -0.334691 0.069 Uiso 1 1 calc R U . . .
H22B H 0.167898 0.290489 -0.247501 0.069 Uiso 1 1 calc R U . . .
N4 N 0.34598(14) 0.18933(14) -0.07862(10) 0.0431(3) Uani 1 1 d . . . . .
C13 C 0.74850(17) 0.31330(18) 0.23628(12) 0.0436(4) Uani 1 1 d . . . . .
H13A H 0.835061 0.372022 0.213229 0.052 Uiso 1 1 calc R U . . .
C15 C 0.6770(2) 0.3454(2) 0.42600(14) 0.0566(4) Uani 1 1 d . . . . .
H15A H 0.583727 0.360251 0.403542 0.068 Uiso 1 1 calc R U . . .
O2 O 1.00852(14) 0.25740(14) 0.30672(10) 0.0554(3) Uani 1 1 d . . . . .
C7 C 0.2006(2) -0.03320(19) 0.04536(15) 0.0524(4) Uani 1 1 d . . . . .
H7A H 0.125976 -0.055103 -0.016762 0.063 Uiso 1 1 calc R U . . .
N2 N 0.54037(16) 0.44752(16) -0.21515(11) 0.0483(3) Uani 1 1 d . . . . .
O1 O 0.82191(12) 0.45488(14) 0.07422(9) 0.0516(3) Uani 1 1 d . . . . .
C4 C 0.44240(17) 0.29595(17) -0.11767(12) 0.0406(3) Uani 1 1 d . . . . .
C5 C 0.41791(16) 0.18072(16) 0.00787(12) 0.0400(3) Uani 1 1 d . . . . .
N3 N 0.57797(14) 0.26904(14) 0.06304(10) 0.0392(3) Uani 1 1 d . . . . .
C12 C 0.61009(17) 0.23949(17) 0.16342(12) 0.0395(3) Uani 1 1 d . . . . .
C14 C 0.77635(18) 0.31019(17) 0.34907(12) 0.0436(4) Uani 1 1 d . . . . .
C11 C 0.46309(18) 0.11739(17) 0.16313(12) 0.0416(3) Uani 1 1 d . . . . .
C6 C 0.35003(17) 0.08219(17) 0.06956(12) 0.0419(3) Uani 1 1 d . . . . .
N1 N 0.65746(15) 0.47339(15) -0.13116(10) 0.0443(3) Uani 1 1 d . . . . .
C2 C 0.60191(17) 0.38444(17) -0.07035(12) 0.0394(3) Uani 1 1 d . . . . .
C1 C 0.68298(17) 0.37848(17) 0.02741(12) 0.0398(3) Uani 1 1 d . . . . .
C3 C 0.40940(19) 0.34067(18) -0.20786(12) 0.0452(4) Uani 1 1 d . . . . .
C16 C 0.7159(3) 0.3587(2) 0.53619(15) 0.0684(6) Uani 1 1 d . . . . .
H16A H 0.648149 0.380909 0.586743 0.082 Uiso 1 1 calc R U . . .
C17 C 0.8545(3) 0.3388(2) 0.56969(15) 0.0676(6) Uani 1 1 d . . . . .
H17A H 0.881102 0.349090 0.643501 0.081 Uiso 1 1 calc R U . . .
C20 C 1.1502(2) 0.2295(3) 0.3368(2) 0.0721(6) Uani 1 1 d . . . . .
H20A H 1.203190 0.208340 0.273437 0.108 Uiso 1 1 calc R U . . .
H20B H 1.221940 0.317343 0.395751 0.108 Uiso 1 1 calc R U . . .
H20C H 1.120866 0.144159 0.361355 0.108 Uiso 1 1 calc R U . . .
C19 C 0.91635(19) 0.28981(17) 0.38603(13) 0.0445(4) Uani 1 1 d . . . . .
C8 C 0.1666(2) -0.1142(2) 0.11644(15) 0.0587(5) Uani 1 1 d . . . . .
H8A H 0.066813 -0.190861 0.102881 0.070 Uiso 1 1 calc R U . . .
C9 C 0.2800(2) -0.08242(19) 0.20816(15) 0.0569(4) Uani 1 1 d . . . . .
H9A H 0.255604 -0.139821 0.254063 0.068 Uiso 1 1 calc R U . . .
C10 C 0.4281(2) 0.03254(18) 0.23245(14) 0.0492(4) Uani 1 1 d . . . . .
H10A H 0.502948 0.052808 0.294006 0.059 Uiso 1 1 calc R U . . .
C21 C 0.8182(2) 0.5833(2) -0.11783(15) 0.0546(4) Uani 1 1 d . . . . .
H21A H 0.820623 0.628778 -0.173875 0.082 Uiso 1 1 calc R U . . .
H21B H 0.844064 0.660430 -0.045514 0.082 Uiso 1 1 calc R U . . .
H21C H 0.895728 0.533007 -0.125316 0.082 Uiso 1 1 calc R U . . .
C18 C 0.9547(2) 0.30380(19) 0.49567(14) 0.0577(5) Uani 1 1 d . . . . .
H18A H 1.047958 0.289590 0.519160 0.069 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'
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
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C24 C23 C22 113.72(16) . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C3 C22 C23 112.84(14) . . ?
C3 C22 H22A 109.0 . . ?
C23 C22 H22A 109.0 . . ?
C3 C22 H22B 109.0 . . ?
C23 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C5 N4 C4 113.43(12) . . ?
C12 C13 C14 126.12(14) . . ?
C12 C13 H13A 116.9 . . ?
C14 C13 H13A 116.9 . . ?
C14 C15 C16 120.77(18) . . ?
C14 C15 H15A 119.6 . . ?
C16 C15 H15A 119.6 . . ?
C19 O2 C20 118.24(14) . . ?
C8 C7 C6 117.93(16) . . ?
C8 C7 H7A 121.0 . . ?
C6 C7 H7A 121.0 . . ?
C3 N2 N1 106.71(13) . . ?
N4 C4 C2 123.87(13) . . ?
N4 C4 C3 130.95(13) . . ?
C2 C4 C3 105.18(14) . . ?
N4 C5 N3 126.41(14) . . ?
N4 C5 C6 127.12(13) . . ?
N3 C5 C6 106.45(12) . . ?
C1 N3 C5 123.17(12) . . ?
C1 N3 C12 126.10(12) . . ?
C5 N3 C12 110.53(12) . . ?
C13 C12 N3 123.97(14) . . ?
C13 C12 C11 131.08(14) . . ?
N3 C12 C11 104.95(12) . . ?
C15 C14 C19 118.02(15) . . ?
C15 C14 C13 121.68(15) . . ?
C19 C14 C13 119.83(14) . . ?
C10 C11 C6 119.52(14) . . ?
C10 C11 C12 131.49(14) . . ?
C6 C11 C12 108.83(13) . . ?
C7 C6 C11 121.75(15) . . ?
C7 C6 C5 129.22(14) . . ?
C11 C6 C5 109.01(13) . . ?
C2 N1 N2 110.90(12) . . ?
C2 N1 C21 128.90(13) . . ?
N2 N1 C21 120.19(13) . . ?
N1 C2 C4 107.19(13) . . ?
N1 C2 C1 129.37(13) . . ?
C4 C2 C1 123.42(14) . . ?
O1 C1 N3 123.65(13) . . ?
O1 C1 C2 126.68(14) . . ?
N3 C1 C2 109.67(12) . . ?
N2 C3 C4 110.01(13) . . ?
N2 C3 C22 121.77(15) . . ?
C4 C3 C22 128.21(15) . . ?
C17 C16 C15 119.64(18) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
C16 C17 C18 120.90(16) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C19 C18 124.21(15) . . ?
O2 C19 C14 114.82(13) . . ?
C18 C19 C14 120.97(16) . . ?
C7 C8 C9 120.66(16) . . ?
C7 C8 H8A 119.7 . . ?
C9 C8 H8A 119.7 . . ?
C10 C9 C8 121.41(17) . . ?
C10 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
C9 C10 C11 118.70(16) . . ?
C9 C10 H10A 120.6 . . ?
C11 C10 H10A 120.6 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C18 C19 119.69(18) . . ?
C17 C18 H18A 120.2 . . ?
C19 C18 H18A 120.2 . . ?
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
C24 C23 1.507(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 C22 1.518(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C22 C3 1.498(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
N4 C5 1.2904(19) . ?
N4 C4 1.381(2) . ?
C13 C12 1.340(2) . ?
C13 C14 1.468(2) . ?
C13 H13A 0.9300 . ?
C15 C14 1.393(2) . ?
C15 C16 1.393(3) . ?
C15 H15A 0.9300 . ?
O2 C19 1.362(2) . ?
O2 C20 1.425(2) . ?
C7 C8 1.381(3) . ?
C7 C6 1.391(2) . ?
C7 H7A 0.9300 . ?
N2 C3 1.332(2) . ?
N2 N1 1.3576(18) . ?
O1 C1 1.2231(18) . ?
C4 C2 1.388(2) . ?
C4 C3 1.411(2) . ?
C5 N3 1.4135(18) . ?
C5 C6 1.452(2) . ?
N3 C1 1.404(2) . ?
N3 C12 1.4420(19) . ?
C12 C11 1.471(2) . ?
C14 C19 1.399(2) . ?
C11 C10 1.390(2) . ?
C11 C6 1.399(2) . ?
N1 C2 1.353(2) . ?
N1 C21 1.456(2) . ?
C2 C1 1.439(2) . ?
C16 C17 1.371(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.374(3) . ?
C17 H17A 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 C18 1.384(2) . ?
C8 C9 1.392(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.381(2) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18 H18A 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C21 H21C O1 0.96 2.51 3.363(2) 148.7 2_765 yes
C21 H21A O2 0.96 2.62 3.466(2) 146.7 2_765 yes
C13 H13A O1 0.93 2.20 2.8509(19) 126.4 . yes
C21 H21C O1 0.96 2.51 3.363(2) 148.7 2_765 yes
C21 H21A O2 0.96 2.62 3.466(2) 146.7 2_765 yes
C13 H13A O1 0.93 2.20 2.8509(19) 126.4 . yes
C13 H13A O1 0.93 2.20 2.8509(19) 126.4 . yes
C21 H21A O2 0.96 2.62 3.466(2) 146.7 2_765 yes
C21 H21C O1 0.96 2.51 3.363(2) 148.7 2_765 yes
C13 H13A O1 0.93 2.20 2.8509(19) 126.4 . yes
C21 H21A O2 0.96 2.62 3.466(2) 146.7 2_765 yes
C21 H21C O1 0.96 2.51 3.363(2) 148.7 2_765 yes
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
C24 C23 C22 C3 -63.3(2) . . . . ?
C5 N4 C4 C2 0.9(2) . . . . ?
C5 N4 C4 C3 -179.17(15) . . . . ?
C4 N4 C5 N3 1.0(2) . . . . ?
C4 N4 C5 C6 179.12(13) . . . . ?
N4 C5 N3 C1 -1.6(2) . . . . ?
C6 C5 N3 C1 179.98(12) . . . . ?
N4 C5 N3 C12 173.51(13) . . . . ?
C6 C5 N3 C12 -4.95(15) . . . . ?
C14 C13 C12 N3 167.01(14) . . . . ?
C14 C13 C12 C11 -13.2(3) . . . . ?
C1 N3 C12 C13 -1.0(2) . . . . ?
C5 N3 C12 C13 -175.84(13) . . . . ?
C1 N3 C12 C11 179.22(12) . . . . ?
C5 N3 C12 C11 4.33(15) . . . . ?
C16 C15 C14 C19 -0.5(2) . . . . ?
C16 C15 C14 C13 -172.64(15) . . . . ?
C12 C13 C14 C15 -53.8(2) . . . . ?
C12 C13 C14 C19 134.13(16) . . . . ?
C13 C12 C11 C10 -6.5(3) . . . . ?
N3 C12 C11 C10 173.29(15) . . . . ?
C13 C12 C11 C6 178.20(15) . . . . ?
N3 C12 C11 C6 -1.99(15) . . . . ?
C8 C7 C6 C11 -0.5(2) . . . . ?
C8 C7 C6 C5 177.99(15) . . . . ?
C10 C11 C6 C7 1.9(2) . . . . ?
C12 C11 C6 C7 177.83(13) . . . . ?
C10 C11 C6 C5 -176.90(13) . . . . ?
C12 C11 C6 C5 -0.96(16) . . . . ?
N4 C5 C6 C7 6.5(3) . . . . ?
N3 C5 C6 C7 -175.07(14) . . . . ?
N4 C5 C6 C11 -174.84(14) . . . . ?
N3 C5 C6 C11 3.60(16) . . . . ?
C3 N2 N1 C2 -0.25(17) . . . . ?
C3 N2 N1 C21 178.72(13) . . . . ?
N2 N1 C2 C4 0.64(17) . . . . ?
C21 N1 C2 C4 -178.22(14) . . . . ?
N2 N1 C2 C1 -177.77(14) . . . . ?
C21 N1 C2 C1 3.4(3) . . . . ?
N4 C4 C2 N1 179.23(12) . . . . ?
C3 C4 C2 N1 -0.74(16) . . . . ?
N4 C4 C2 C1 -2.2(2) . . . . ?
C3 C4 C2 C1 177.78(13) . . . . ?
C5 N3 C1 O1 -179.60(13) . . . . ?
C12 N3 C1 O1 6.1(2) . . . . ?
C5 N3 C1 C2 0.19(18) . . . . ?
C12 N3 C1 C2 -174.10(12) . . . . ?
N1 C2 C1 O1 -0.5(3) . . . . ?
C4 C2 C1 O1 -178.68(14) . . . . ?
N1 C2 C1 N3 179.71(13) . . . . ?
C4 C2 C1 N3 1.54(19) . . . . ?
N1 N2 C3 C4 -0.24(17) . . . . ?
N1 N2 C3 C22 -179.40(14) . . . . ?
N4 C4 C3 N2 -179.36(14) . . . . ?
C2 C4 C3 N2 0.61(17) . . . . ?
N4 C4 C3 C22 -0.3(3) . . . . ?
C2 C4 C3 C22 179.71(15) . . . . ?
C23 C22 C3 N2 112.45(18) . . . . ?
C23 C22 C3 C4 -66.5(2) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C20 O2 C19 C18 2.8(2) . . . . ?
C20 O2 C19 C14 -177.74(15) . . . . ?
C15 C14 C19 O2 -179.27(13) . . . . ?
C13 C14 C19 O2 -7.0(2) . . . . ?
C15 C14 C19 C18 0.2(2) . . . . ?
C13 C14 C19 C18 172.49(14) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C7 C8 C9 C10 1.4(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C6 C11 C10 C9 -1.6(2) . . . . ?
C12 C11 C10 C9 -176.43(15) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
O2 C19 C18 C17 179.15(15) . . . . ?
C14 C19 C18 C17 -0.2(2) . . . . ?
