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#$Date: 2024-01-06 11:40:31 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288890 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/96/7159692.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_7159692
loop_
_publ_author_name
'Takallou, Ahmad'
'Al-Siyabi, Munir'
'Al-Shidhani, Sulaiman'
'Lotfi Nosood, Yazdanbakhsh'
'Habibi, Azizollah'
'Almaani, Alhajaj'
'Anwar, Muhammad U.'
'Al-Harrasi, Ahmed'
_publ_section_title
;
 Preparation of pyridopyrazines through tandem Pd-catalyzed C-N/C-C
 coupling reactions of Ugi adducts.
;
_journal_issue                   48
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9530
_journal_page_last               9533
_journal_paper_doi               10.1039/d3ob01768k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C25 H21 F N2 O2'
_chemical_formula_weight         400.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;FinalCif V121 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-05-28 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.6450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9745(6)
_cell_length_b                   20.9846(8)
_cell_length_c                   7.8209(4)
_cell_measurement_reflns_used    6167
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.344
_cell_measurement_theta_min      2.7865
_cell_volume                     1993.27(15)
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_collection
'Bruker BIS V6.2.16/2021-10-23 && APEX4 2022.10-0'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11556
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.786
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.483
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1538 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_extinction_coef       0.0093(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4066
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0350
_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)+(0.0357P)²+0.5586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.986
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3500
_reflns_number_total             4066
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01768k2.cif
_cod_data_source_block           MU39_P_R1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7159692--7159693.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7159692
_shelx_shelxl_version_number     2019/1
_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_min   0.957
_shelx_estimated_absorpt_t_max   0.996
_diffrn_measurement_ambient_temperature_device_make '296 K'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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
F1 F 0.10686(16) 0.42195(12) 0.4441(3) 0.0842(7) Uani 1 1 d . . . . .
O1 O 0.53274(17) 0.52744(9) 0.4561(3) 0.0507(5) Uani 1 1 d . . . . .
O2 O 0.36969(16) 0.34533(11) 0.0206(3) 0.0577(6) Uani 1 1 d . . . . .
N1 N 0.56969(16) 0.42209(9) 0.4678(3) 0.0337(5) Uani 1 1 d . . . . .
N2 N 0.53981(18) 0.31150(10) 0.2544(3) 0.0401(5) Uani 1 1 d . . . . .
C1 C 0.6978(2) 0.49048(13) 0.7305(4) 0.0383(6) Uani 1 1 d . . . . .
C2 C 0.7586(2) 0.43792(13) 0.8382(4) 0.0400(6) Uani 1 1 d . . . . .
C3 C 0.8560(2) 0.44873(16) 1.0166(4) 0.0514(7) Uani 1 1 d . . . . .
H3 H 0.897460 0.414337 1.091740 0.062 Uiso 1 1 calc R U . . .
C4 C 0.8902(2) 0.50966(18) 1.0807(5) 0.0597(9) Uani 1 1 d . . . . .
H4 H 0.955388 0.516198 1.198238 0.072 Uiso 1 1 calc R U . . .
C5 C 0.8294(3) 0.56140(17) 0.9732(5) 0.0597(9) Uani 1 1 d . . . . .
H5 H 0.853408 0.602505 1.018676 0.072 Uiso 1 1 calc R U . . .
C6 C 0.7330(2) 0.55221(14) 0.7986(4) 0.0483(7) Uani 1 1 d . . . . .
H6 H 0.691631 0.587036 0.726354 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5950(2) 0.48306(12) 0.5431(4) 0.0362(6) Uani 1 1 d . . . . .
C8 C 0.63457(19) 0.36927(11) 0.5646(4) 0.0343(6) Uani 1 1 d . . . . .
C9 C 0.7229(2) 0.37415(12) 0.7565(4) 0.0373(6) Uani 1 1 d . . . . .
C10 C 0.46130(19) 0.41272(12) 0.2945(4) 0.0355(6) Uani 1 1 d . . . . .
H10 H 0.450460 0.448478 0.206042 0.043 Uiso 1 1 calc R U . . .
C11 C 0.4527(2) 0.35239(13) 0.1792(4) 0.0396(6) Uani 1 1 d . . . . .
C12 C 0.6118(2) 0.31123(12) 0.4624(4) 0.0385(6) Uani 1 1 d . . . . .
C13 C 0.6617(3) 0.25668(13) 0.5674(5) 0.0514(7) Uani 1 1 d . . . . .
H13 H 0.640155 0.217126 0.506387 0.062 Uiso 1 1 calc R U . . .
C14 C 0.7434(3) 0.26029(14) 0.7627(5) 0.0564(8) Uani 1 1 d . . . . .
H14 H 0.775781 0.223172 0.832438 0.068 Uiso 1 1 calc R U . . .
C15 C 0.7767(3) 0.31827(14) 0.8535(4) 0.0510(7) Uani 1 1 d . . . . .
H15 H 0.835750 0.320484 0.981123 0.061 Uiso 1 1 calc R U . . .
C16 C 0.3676(2) 0.41627(11) 0.3406(4) 0.0357(6) Uani 1 1 d . . . . .
C17 C 0.3837(2) 0.40846(13) 0.5272(4) 0.0417(6) Uani 1 1 d . . . . .
H17 H 0.454670 0.401940 0.631029 0.050 Uiso 1 1 calc R U . . .
C18 C 0.2965(2) 0.41008(15) 0.5641(5) 0.0514(7) Uani 1 1 d . . . . .
H18 H 0.307870 0.404714 0.690888 0.062 Uiso 1 1 calc R U . . .
C19 C 0.1934(2) 0.41979(16) 0.4091(5) 0.0551(8) Uani 1 1 d . . . . .
C20 C 0.1738(2) 0.42876(18) 0.2223(5) 0.0611(9) Uani 1 1 d . . . . .
H20 H 0.102620 0.435787 0.119798 0.073 Uiso 1 1 calc R U . . .
C21 C 0.2613(2) 0.42725(15) 0.1877(4) 0.0507(7) Uani 1 1 d . . . . .
H21 H 0.249181 0.433629 0.060835 0.061 Uiso 1 1 calc R U . . .
C22 C 0.5544(2) 0.26460(13) 0.1198(4) 0.0458(7) Uani 1 1 d . . . . .
C23 C 0.4890(3) 0.20422(15) 0.0984(6) 0.0667(10) Uani 1 1 d . . . . .
H23A H 0.491344 0.176830 0.002248 0.100 Uiso 1 1 calc R U . . .
H23B H 0.413956 0.215186 0.056913 0.100 Uiso 1 1 calc R U . . .
H23C H 0.520518 0.182550 0.222688 0.100 Uiso 1 1 calc R U . . .
C24 C 0.6765(3) 0.25148(16) 0.1990(5) 0.0567(8) Uani 1 1 d . . . . .
H24A H 0.685869 0.227828 0.103184 0.085 Uiso 1 1 calc R U . . .
H24B H 0.705036 0.227208 0.318342 0.085 Uiso 1 1 calc R U . . .
H24C H 0.715533 0.291151 0.225259 0.085 Uiso 1 1 calc R U . . .
C25 C 0.5138(3) 0.29529(17) -0.0826(5) 0.0604(8) Uani 1 1 d . . . . .
H25A H 0.537586 0.270120 -0.157121 0.091 Uiso 1 1 calc R U . . .
H25B H 0.543544 0.337521 -0.065904 0.091 Uiso 1 1 calc R U . . .
H25C H 0.434831 0.297445 -0.151290 0.091 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'
F F 0.0171 0.0103 '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
C7 N1 C8 123.0(2) . . ?
C7 N1 C10 116.7(2) . . ?
C8 N1 C10 119.57(19) . . ?
C11 N2 C12 118.0(2) . . ?
C11 N2 C22 120.3(2) . . ?
C12 N2 C22 121.6(2) . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 C7 121.5(2) . . ?
C6 C1 C7 117.8(2) . . ?
C1 C2 C3 118.3(2) . . ?
C1 C2 C9 119.1(2) . . ?
C3 C2 C9 122.4(3) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O1 C7 N1 120.4(2) . . ?
O1 C7 C1 123.3(2) . . ?
N1 C7 C1 116.2(2) . . ?
N1 C8 C9 121.1(2) . . ?
N1 C8 C12 118.5(2) . . ?
C9 C8 C12 120.4(2) . . ?
C15 C9 C8 118.3(2) . . ?
C15 C9 C2 123.8(2) . . ?
C8 C9 C2 117.8(2) . . ?
N1 C10 C16 113.0(2) . . ?
N1 C10 C11 113.7(2) . . ?
C16 C10 C11 110.8(2) . . ?
N1 C10 H10 106.2 . . ?
C16 C10 H10 106.2 . . ?
C11 C10 H10 106.2 . . ?
O2 C11 N2 124.1(2) . . ?
O2 C11 C10 117.4(2) . . ?
N2 C11 C10 118.4(2) . . ?
C13 C12 C8 118.4(2) . . ?
C13 C12 N2 123.0(2) . . ?
C8 C12 N2 118.6(2) . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C9 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C9 C15 H15 119.6 . . ?
C17 C16 C21 118.6(2) . . ?
C17 C16 C10 122.6(2) . . ?
C21 C16 C10 118.8(2) . . ?
C16 C17 C18 121.4(2) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 118.0(3) . . ?
C19 C18 H18 121.0 . . ?
C17 C18 H18 121.0 . . ?
C20 C19 C18 122.6(3) . . ?
C20 C19 F1 118.9(3) . . ?
C18 C19 F1 118.5(3) . . ?
C19 C20 C21 118.8(3) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C20 C21 C16 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C23 C22 C24 112.6(3) . . ?
C23 C22 N2 109.6(2) . . ?
C24 C22 N2 109.9(2) . . ?
C23 C22 C25 109.9(3) . . ?
C24 C22 C25 105.2(3) . . ?
N2 C22 C25 109.5(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
F1 C19 1.366(3) . ?
O1 C7 1.225(3) . ?
O2 C11 1.217(3) . ?
N1 C7 1.379(3) . ?
N1 C8 1.394(3) . ?
N1 C10 1.463(3) . ?
N2 C11 1.362(3) . ?
N2 C12 1.429(3) . ?
N2 C22 1.526(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.395(4) . ?
C1 C7 1.467(3) . ?
C2 C3 1.404(4) . ?
C2 C9 1.461(4) . ?
C3 C4 1.370(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.397(3) . ?
C8 C12 1.404(3) . ?
C9 C15 1.397(4) . ?
C10 C16 1.522(4) . ?
C10 C11 1.524(4) . ?
C10 H10 0.9800 . ?
C12 C13 1.380(4) . ?
C13 C14 1.385(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.372(4) . ?
C16 C21 1.390(4) . ?
C17 C18 1.386(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.360(5) . ?
C20 C21 1.378(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.522(4) . ?
C22 C24 1.526(4) . ?
C22 C25 1.534(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C6 C1 C2 C3 0.1(4) . . . . ?
C7 C1 C2 C3 -179.8(3) . . . . ?
C6 C1 C2 C9 -176.2(3) . . . . ?
C7 C1 C2 C9 3.9(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C9 C2 C3 C4 175.4(3) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C7 C1 C6 C5 -179.6(3) . . . . ?
C8 N1 C7 O1 -176.9(2) . . . . ?
C10 N1 C7 O1 -6.5(4) . . . . ?
C8 N1 C7 C1 2.3(3) . . . . ?
C10 N1 C7 C1 172.7(2) . . . . ?
C2 C1 C7 O1 171.1(3) . . . . ?
C6 C1 C7 O1 -8.8(4) . . . . ?
C2 C1 C7 N1 -8.0(3) . . . . ?
C6 C1 C7 N1 172.1(2) . . . . ?
C7 N1 C8 C9 7.8(4) . . . . ?
C10 N1 C8 C9 -162.4(2) . . . . ?
C7 N1 C8 C12 -169.9(2) . . . . ?
C10 N1 C8 C12 19.9(3) . . . . ?
N1 C8 C9 C15 172.7(2) . . . . ?
C12 C8 C9 C15 -9.6(4) . . . . ?
N1 C8 C9 C2 -11.8(3) . . . . ?
C12 C8 C9 C2 165.9(2) . . . . ?
C1 C2 C9 C15 -178.8(3) . . . . ?
C3 C2 C9 C15 5.0(4) . . . . ?
C1 C2 C9 C8 6.0(4) . . . . ?
C3 C2 C9 C8 -170.2(2) . . . . ?
C7 N1 C10 C16 -72.0(3) . . . . ?
C8 N1 C10 C16 98.7(3) . . . . ?
C7 N1 C10 C11 160.5(2) . . . . ?
C8 N1 C10 C11 -28.8(3) . . . . ?
C12 N2 C11 O2 -157.6(3) . . . . ?
C22 N2 C11 O2 18.4(4) . . . . ?
C12 N2 C11 C10 25.8(3) . . . . ?
C22 N2 C11 C10 -158.2(2) . . . . ?
N1 C10 C11 O2 -171.3(2) . . . . ?
C16 C10 C11 O2 60.1(3) . . . . ?
N1 C10 C11 N2 5.5(3) . . . . ?
C16 C10 C11 N2 -123.1(3) . . . . ?
N1 C8 C12 C13 -168.2(3) . . . . ?
C9 C8 C12 C13 14.1(4) . . . . ?
N1 C8 C12 N2 12.9(3) . . . . ?
C9 C8 C12 N2 -164.8(2) . . . . ?
C11 N2 C12 C13 144.6(3) . . . . ?
C22 N2 C12 C13 -31.3(4) . . . . ?
C11 N2 C12 C8 -36.5(3) . . . . ?
C22 N2 C12 C8 147.6(2) . . . . ?
C8 C12 C13 C14 -8.8(4) . . . . ?
N2 C12 C13 C14 170.1(3) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C13 C14 C15 C9 5.4(5) . . . . ?
C8 C9 C15 C14 -0.1(4) . . . . ?
C2 C9 C15 C14 -175.3(3) . . . . ?
N1 C10 C16 C17 -19.6(3) . . . . ?
C11 C10 C16 C17 109.4(3) . . . . ?
N1 C10 C16 C21 161.0(2) . . . . ?
C11 C10 C16 C21 -69.9(3) . . . . ?
C21 C16 C17 C18 1.3(4) . . . . ?
C10 C16 C17 C18 -178.1(3) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 C20 -1.0(5) . . . . ?
C17 C18 C19 F1 -179.5(3) . . . . ?
C18 C19 C20 C21 0.8(6) . . . . ?
F1 C19 C20 C21 179.3(3) . . . . ?
C19 C20 C21 C16 0.5(5) . . . . ?
C17 C16 C21 C20 -1.5(4) . . . . ?
C10 C16 C21 C20 177.9(3) . . . . ?
C11 N2 C22 C23 -86.4(3) . . . . ?
C12 N2 C22 C23 89.5(3) . . . . ?
C11 N2 C22 C24 149.4(3) . . . . ?
C12 N2 C22 C24 -34.8(3) . . . . ?
C11 N2 C22 C25 34.3(3) . . . . ?
C12 N2 C22 C25 -149.9(2) . . . . ?
