#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/23/2222357.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222357
loop_
_publ_author_name
'Zhu, Xiao-Tong'
'Zhang, Ge'
'Ma, Ning'
_publ_section_title
;2-Amino-5,7-bis(4-fluorophenyl)-1',3'-dimethyl-7,8-dihydrospiro[pyrido[2,3-d]pyrimidine-6(5H),5'-pyrimidine]-2',4,4',6'(3H,1'H,3'H,5'H)-tetraone
 ethanol solvate
;
_journal_coeditor_code           HK2707
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1625
_journal_paper_doi               10.1107/S1600536809022946
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C24 H20 F2 N6 O4, C2 H6 O'
_chemical_formula_moiety         'C24 H20 F2 N6 O4, C2 H6 O'
_chemical_formula_sum            'C26 H26 F2 N6 O5'
_chemical_formula_weight         540.53
_chemical_melting_point_gt       573
_chemical_name_systematic
;
2-Amino-5,7-bis(4-fluorophenyl)-1',3'-dimethyl-7,8-
dihydrospiro[pyrido[2,3-d]pyrimidine-6(5H),5'-pyrimidine]-
2',4,4',6'(3H,1'H,3'H,5'H)-tetraone ethanol
solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                64.634(2)
_cell_angle_beta                 81.467(3)
_cell_angle_gamma                69.027(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2189(15)
_cell_length_b                   12.5924(17)
_cell_length_c                   14.100(2)
_cell_measurement_reflns_used    1085
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.236
_cell_measurement_theta_min      2.505
_cell_volume                     1381.0(4)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0919
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7223
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1526
_refine_ls_R_factor_gt           0.0664
_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)+(0.0296P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                1979
_reflns_number_total             4773
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2707.cif
_cod_data_source_block           I
_cod_database_code               2222357
_cod_database_fobs_code          2222357
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 -0.6967(3) 0.6507(3) 0.4242(2) 0.1682(12) Uani d . 1 . .
F F2 0.5065(3) -0.0663(2) 0.3998(2) 0.1646(12) Uani d . 1 . .
O O1 0.3825(3) 0.4015(2) 0.05479(17) 0.0724(7) Uani d . 1 . .
O O2 -0.1950(3) 0.3213(2) 0.1939(2) 0.0921(9) Uani d . 1 . .
O O3 -0.0319(4) 0.1522(3) 0.5289(2) 0.1190(11) Uani d . 1 . .
O O4 0.0495(3) 0.5117(2) 0.31565(17) 0.0687(7) Uani d . 1 . .
O O5 0.8805(3) 0.9228(2) 0.0997(2) 0.0952(8) Uani d . 1 . .
H H5 0.9547 0.9075 0.0620 0.143 Uiso calc R 1 . .
N N1 -0.1126(3) 0.6500(2) 0.1209(2) 0.0631(8) Uani d . 1 . .
H H1 -0.1678 0.7246 0.1130 0.076 Uiso calc R 1 . .
N N2 0.0779(3) 0.7345(2) 0.0419(2) 0.0641(8) Uani d . 1 . .
N N3 0.3234(3) 0.6058(3) 0.01820(19) 0.0644(8) Uani d . 1 . .
H H3 0.4169 0.6010 -0.0035 0.077 Uiso calc R 1 . .
N N4 0.2777(3) 0.8125(3) -0.0313(2) 0.0967(11) Uani d . 1 . .
H H4A 0.2176 0.8855 -0.0376 0.116 Uiso calc R 1 . .
H H4B 0.3725 0.8012 -0.0519 0.116 Uiso calc R 1 . .
N N5 -0.1246(3) 0.2430(3) 0.3629(3) 0.0754(9) Uani d . 1 . .
N N6 0.0080(3) 0.3332(3) 0.4216(2) 0.0633(8) Uani d . 1 . .
C C1 0.0370(4) 0.6286(3) 0.0878(2) 0.0542(9) Uani d . 1 . .
C C2 0.2236(5) 0.7165(4) 0.0104(3) 0.0666(10) Uani d . 1 . .
C C3 0.2842(4) 0.4988(3) 0.0593(2) 0.0572(9) Uani d . 1 . .
C C4 0.1348(4) 0.5102(3) 0.1027(2) 0.0511(8) Uani d . 1 . .
C C5 0.0803(3) 0.3989(3) 0.1575(2) 0.0534(9) Uani d . 1 . .
H H5A 0.0389 0.3884 0.1031 0.064 Uiso calc R 1 . .
C C6 -0.0593(3) 0.4266(3) 0.2334(2) 0.0508(8) Uani d . 1 . .
C C7 -0.1839(4) 0.5532(3) 0.1689(3) 0.0587(9) Uani d . 1 . .
H H7 -0.2202 0.5436 0.1121 0.070 Uiso calc R 1 . .
C C8 -0.1336(4) 0.3270(3) 0.2608(3) 0.0645(10) Uani d . 1 . .
C C9 -0.0484(5) 0.2372(4) 0.4437(3) 0.0788(12) Uani d . 1 . .
C C10 0.0015(4) 0.4300(3) 0.3251(3) 0.0551(9) Uani d . 1 . .
C C11 -0.1894(5) 0.1422(4) 0.3883(3) 0.1337(18) Uani d . 1 . .
H H11A -0.2645 0.1673 0.3358 0.201 Uiso calc R 1 . .
H H11B -0.2387 0.1255 0.4557 0.201 Uiso calc R 1 . .
H H11C -0.1073 0.0683 0.3900 0.201 Uiso calc R 1 . .
C C12 0.0864(4) 0.3261(4) 0.5089(3) 0.0979(13) Uani d . 1 . .
H H12A 0.0106 0.3622 0.5507 0.147 Uiso calc R 1 . .
H H12B 0.1590 0.3710 0.4813 0.147 Uiso calc R 1 . .
H H12C 0.1408 0.2406 0.5517 0.147 Uiso calc R 1 . .
C C13 0.2024(4) 0.2751(3) 0.2181(3) 0.0566(9) Uani d . 1 . .
C C14 0.2005(5) 0.1674(4) 0.2162(3) 0.0923(13) Uani d . 1 . .
H H14 0.1292 0.1720 0.1731 0.111 Uiso calc R 1 . .
C C15 0.3015(6) 0.0531(4) 0.2763(4) 0.1288(19) Uani d . 1 . .
H H15 0.2984 -0.0190 0.2744 0.155 Uiso calc R 1 . .
C C16 0.4049(6) 0.0471(4) 0.3381(4) 0.1049(15) Uani d . 1 . .
C C17 0.4125(4) 0.1504(4) 0.3425(3) 0.0855(12) Uani d . 1 . .
H H17 0.4847 0.1443 0.3858 0.103 Uiso calc R 1 . .
C C18 0.3109(4) 0.2647(3) 0.2815(3) 0.0658(10) Uani d . 1 . .
H H18 0.3160 0.3362 0.2834 0.079 Uiso calc R 1 . .
C C19 -0.3239(4) 0.5881(3) 0.2339(3) 0.0614(9) Uani d . 1 . .
C C20 -0.4521(4) 0.5589(3) 0.2302(3) 0.0846(12) Uani d . 1 . .
H H20 -0.4539 0.5245 0.1839 0.102 Uiso calc R 1 . .
C C21 -0.5790(5) 0.5796(4) 0.2940(4) 0.1103(16) Uani d . 1 . .
H H21 -0.6653 0.5586 0.2921 0.132 Uiso calc R 1 . .
C C22 -0.5731(6) 0.6310(5) 0.3588(4) 0.1072(16) Uani d . 1 . .
C C23 -0.4515(5) 0.6654(4) 0.3646(3) 0.1005(14) Uani d . 1 . .
H H23 -0.4530 0.7024 0.4096 0.121 Uiso calc R 1 . .
C C24 -0.3249(4) 0.6426(3) 0.3002(3) 0.0776(11) Uani d . 1 . .
H H24 -0.2395 0.6646 0.3021 0.093 Uiso calc R 1 . .
C C25 0.9345(6) 0.8842(4) 0.2021(3) 0.1126(15) Uani d D 1 . .
H H25A 0.9644 0.7943 0.2376 0.135 Uiso calc R 1 . .
H H25B 0.8507 0.9193 0.2416 0.135 Uiso calc R 1 . .
C C26 1.0640(7) 0.9217(5) 0.2010(4) 0.168(2) Uani d D 1 . .
H H26A 1.1452 0.8910 0.1588 0.251 Uiso calc R 1 . .
H H26B 1.1015 0.8884 0.2713 0.251 Uiso calc R 1 . .
H H26C 1.0323 1.0109 0.1720 0.251 Uiso calc R 1 . .
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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C7 . . 123.3(3) ?
C1 N1 H1 . . 118.3 ?
C7 N1 H1 . . 118.3 ?
C2 N2 C1 . . 114.7(3) ?
C2 N3 C3 . . 123.3(3) ?
C2 N3 H3 . . 118.4 ?
C3 N3 H3 . . 118.4 ?
C2 N4 H4A . . 120.0 ?
C2 N4 H4B . . 120.0 ?
H4A N4 H4B . . 120.0 ?
C8 N5 C9 . . 125.8(3) ?
C8 N5 C11 . . 117.4(3) ?
C9 N5 C11 . . 116.5(4) ?
C10 N6 C9 . . 125.3(3) ?
C10 N6 C12 . . 118.7(3) ?
C9 N6 C12 . . 116.0(3) ?
C25 O5 H5 . . 109.5 ?
N1 C1 N2 . . 113.2(3) ?
N1 C1 C4 . . 121.5(3) ?
N2 C1 C4 . . 125.3(3) ?
N2 C2 N3 . . 123.5(3) ?
N2 C2 N4 . . 119.7(4) ?
N3 C2 N4 . . 116.8(4) ?
O1 C3 N3 . . 118.3(3) ?
O1 C3 C4 . . 126.1(3) ?
N3 C3 C4 . . 115.6(3) ?
C1 C4 C3 . . 117.1(3) ?
C1 C4 C5 . . 121.4(3) ?
C3 C4 C5 . . 121.4(3) ?
C4 C5 C13 . . 116.7(3) ?
C4 C5 C6 . . 109.9(3) ?
C13 C5 C6 . . 109.1(2) ?
C4 C5 H5A . . 106.9 ?
C13 C5 H5A . . 106.9 ?
C6 C5 H5A . . 106.9 ?
C10 C6 C8 . . 115.5(3) ?
C10 C6 C7 . . 111.9(3) ?
C8 C6 C7 . . 106.2(3) ?
C10 C6 C5 . . 109.1(2) ?
C8 C6 C5 . . 105.7(3) ?
C7 C6 C5 . . 108.1(2) ?
N1 C7 C19 . . 112.1(3) ?
N1 C7 C6 . . 109.7(2) ?
C19 C7 C6 . . 112.5(3) ?
N1 C7 H7 . . 107.4 ?
C19 C7 H7 . . 107.4 ?
C6 C7 H7 . . 107.4 ?
O2 C8 N5 . . 121.6(3) ?
O2 C8 C6 . . 120.8(4) ?
N5 C8 C6 . . 117.5(3) ?
O3 C9 N6 . . 121.7(4) ?
O3 C9 N5 . . 121.5(4) ?
N6 C9 N5 . . 116.9(4) ?
O4 C10 N6 . . 119.6(3) ?
O4 C10 C6 . . 122.3(3) ?
N6 C10 C6 . . 118.0(3) ?
N5 C11 H11A . . 109.5 ?
N5 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N5 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N6 C12 H12A . . 109.5 ?
N6 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N6 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C18 C13 C14 . . 117.5(3) ?
C18 C13 C5 . . 122.3(3) ?
C14 C13 C5 . . 120.1(3) ?
C15 C14 C13 . . 121.6(4) ?
C15 C14 H14 . . 119.2 ?
C13 C14 H14 . . 119.2 ?
C16 C15 C14 . . 118.9(4) ?
C16 C15 H15 . . 120.5 ?
C14 C15 H15 . . 120.5 ?
C15 C16 C17 . . 122.0(4) ?
C15 C16 F2 . . 120.1(5) ?
C17 C16 F2 . . 117.9(5) ?
C16 C17 C18 . . 118.6(4) ?
C16 C17 H17 . . 120.7 ?
C18 C17 H17 . . 120.7 ?
C13 C18 C17 . . 121.4(4) ?
C13 C18 H18 . . 119.3 ?
C17 C18 H18 . . 119.3 ?
C20 C19 C24 . . 118.7(3) ?
C20 C19 C7 . . 118.7(4) ?
C24 C19 C7 . . 122.5(3) ?
C19 C20 C21 . . 121.3(4) ?
C19 C20 H20 . . 119.3 ?
C21 C20 H20 . . 119.3 ?
C22 C21 C20 . . 117.6(4) ?
C22 C21 H21 . . 121.2 ?
C20 C21 H21 . . 121.2 ?
C21 C22 C23 . . 124.2(4) ?
C21 C22 F1 . . 118.7(5) ?
C23 C22 F1 . . 117.0(5) ?
C22 C23 C24 . . 117.0(4) ?
C22 C23 H23 . . 121.5 ?
C24 C23 H23 . . 121.5 ?
C19 C24 C23 . . 121.1(4) ?
C19 C24 H24 . . 119.5 ?
C23 C24 H24 . . 119.5 ?
O5 C25 C26 . . 112.3(4) ?
O5 C25 H25A . . 109.1 ?
C26 C25 H25A . . 109.1 ?
O5 C25 H25B . . 109.1 ?
C26 C25 H25B . . 109.1 ?
H25A C25 H25B . . 107.9 ?
C25 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C25 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C22 . 1.376(5) ?
F2 C16 . 1.376(4) ?
N1 C1 . 1.357(4) ?
N1 C7 . 1.453(3) ?
N1 H1 . 0.8600 ?
N2 C2 . 1.320(4) ?
N2 C1 . 1.374(4) ?
N3 C2 . 1.335(4) ?
N3 C3 . 1.378(4) ?
N3 H3 . 0.8600 ?
N4 C2 . 1.338(4) ?
N4 H4A . 0.8600 ?
N4 H4B . 0.8600 ?
N5 C8 . 1.366(4) ?
N5 C9 . 1.388(4) ?
N5 C11 . 1.478(4) ?
N6 C10 . 1.375(4) ?
N6 C9 . 1.382(4) ?
N6 C12 . 1.474(4) ?
O1 C3 . 1.258(3) ?
O2 C8 . 1.209(4) ?
O3 C9 . 1.203(4) ?
O4 C10 . 1.210(3) ?
O5 C25 . 1.418(4) ?
O5 H5 . 0.8200 ?
C1 C4 . 1.380(4) ?
C3 C4 . 1.406(4) ?
C4 C5 . 1.508(4) ?
C5 C13 . 1.522(4) ?
C5 C6 . 1.585(4) ?
C5 H5A . 0.9800 ?
C6 C10 . 1.507(4) ?
C6 C8 . 1.521(4) ?
C6 C7 . 1.564(4) ?
C7 C19 . 1.511(4) ?
C7 H7 . 0.9800 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C18 . 1.374(4) ?
C13 C14 . 1.375(4) ?
C14 C15 . 1.373(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.346(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.355(5) ?
C17 C18 . 1.379(4) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 C20 . 1.372(4) ?
C19 C24 . 1.374(4) ?
C20 C21 . 1.384(5) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.343(6) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.363(5) ?
C23 C24 . 1.392(5) ?
C23 H23 . 0.9300 ?
C24 H24 . 0.9300 ?
C25 C26 . 1.428(5) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3 O1 2_665 0.86 1.88 2.737(3) 177 yes
N4 H4A O5 2_675 0.86 2.07 2.890(3) 160 yes
O5 H5 N2 1_655 0.82 2.19 2.779(3) 129 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 N2 . . . . 178.1(3) ?
C7 N1 C1 C4 . . . . -3.3(5) ?
C2 N2 C1 N1 . . . . 178.9(3) ?
C2 N2 C1 C4 . . . . 0.4(5) ?
C1 N2 C2 N3 . . . . 2.5(5) ?
C1 N2 C2 N4 . . . . -177.2(3) ?
C3 N3 C2 N2 . . . . 0.5(5) ?
C3 N3 C2 N4 . . . . -179.8(3) ?
C2 N3 C3 O1 . . . . 173.9(3) ?
C2 N3 C3 C4 . . . . -6.0(5) ?
N1 C1 C4 C3 . . . . 175.8(3) ?
N2 C1 C4 C3 . . . . -5.8(5) ?
N1 C1 C4 C5 . . . . -0.6(5) ?
N2 C1 C4 C5 . . . . 177.8(3) ?
O1 C3 C4 C1 . . . . -171.8(3) ?
N3 C3 C4 C1 . . . . 8.1(4) ?
O1 C3 C4 C5 . . . . 4.6(5) ?
N3 C3 C4 C5 . . . . -175.5(3) ?
C1 C4 C5 C13 . . . . -149.9(3) ?
C3 C4 C5 C13 . . . . 33.9(4) ?
C1 C4 C5 C6 . . . . -25.0(4) ?
C3 C4 C5 C6 . . . . 158.7(3) ?
C4 C5 C6 C10 . . . . -70.3(3) ?
C13 C5 C6 C10 . . . . 58.8(3) ?
C4 C5 C6 C8 . . . . 164.9(3) ?
C13 C5 C6 C8 . . . . -66.0(3) ?
C4 C5 C6 C7 . . . . 51.5(3) ?
C13 C5 C6 C7 . . . . -179.4(3) ?
C1 N1 C7 C19 . . . . 158.4(3) ?
C1 N1 C7 C6 . . . . 32.6(4) ?
C10 C6 C7 N1 . . . . 65.0(3) ?
C8 C6 C7 N1 . . . . -168.2(3) ?
C5 C6 C7 N1 . . . . -55.2(3) ?
C10 C6 C7 C19 . . . . -60.5(4) ?
C8 C6 C7 C19 . . . . 66.3(4) ?
C5 C6 C7 C19 . . . . 179.3(3) ?
C9 N5 C8 O2 . . . . 175.8(4) ?
C11 N5 C8 O2 . . . . 1.5(5) ?
C9 N5 C8 C6 . . . . -2.5(5) ?
C11 N5 C8 C6 . . . . -176.8(3) ?
C10 C6 C8 O2 . . . . 175.2(3) ?
C7 C6 C8 O2 . . . . 50.6(4) ?
C5 C6 C8 O2 . . . . -64.1(4) ?
C10 C6 C8 N5 . . . . -6.4(4) ?
C7 C6 C8 N5 . . . . -131.0(3) ?
C5 C6 C8 N5 . . . . 114.3(3) ?
C10 N6 C9 O3 . . . . 176.3(3) ?
C12 N6 C9 O3 . . . . -1.1(5) ?
C10 N6 C9 N5 . . . . -3.5(5) ?
C12 N6 C9 N5 . . . . 179.1(3) ?
C8 N5 C9 O3 . . . . -171.9(4) ?
C11 N5 C9 O3 . . . . 2.4(6) ?
C8 N5 C9 N6 . . . . 7.8(5) ?
C11 N5 C9 N6 . . . . -177.9(3) ?
C9 N6 C10 O4 . . . . 177.2(3) ?
C12 N6 C10 O4 . . . . -5.5(5) ?
C9 N6 C10 C6 . . . . -5.5(5) ?
C12 N6 C10 C6 . . . . 171.9(3) ?
C8 C6 C10 O4 . . . . -172.6(3) ?
C7 C6 C10 O4 . . . . -51.0(4) ?
C5 C6 C10 O4 . . . . 68.6(4) ?
C8 C6 C10 N6 . . . . 10.1(4) ?
C7 C6 C10 N6 . . . . 131.7(3) ?
C5 C6 C10 N6 . . . . -108.7(3) ?
C4 C5 C13 C18 . . . . 43.5(4) ?
C6 C5 C13 C18 . . . . -81.7(4) ?
C4 C5 C13 C14 . . . . -140.8(3) ?
C6 C5 C13 C14 . . . . 94.0(4) ?
C18 C13 C14 C15 . . . . 0.9(6) ?
C5 C13 C14 C15 . . . . -174.9(4) ?
C13 C14 C15 C16 . . . . -0.3(7) ?
C14 C15 C16 C17 . . . . -0.1(8) ?
C14 C15 C16 F2 . . . . 179.5(4) ?
C15 C16 C17 C18 . . . . -0.1(7) ?
F2 C16 C17 C18 . . . . -179.7(3) ?
C14 C13 C18 C17 . . . . -1.2(5) ?
C5 C13 C18 C17 . . . . 174.6(3) ?
C16 C17 C18 C13 . . . . 0.8(6) ?
N1 C7 C19 C20 . . . . 139.9(3) ?
C6 C7 C19 C20 . . . . -95.8(4) ?
N1 C7 C19 C24 . . . . -43.2(4) ?
C6 C7 C19 C24 . . . . 81.1(4) ?
C24 C19 C20 C21 . . . . -2.1(6) ?
C7 C19 C20 C21 . . . . 174.9(4) ?
C19 C20 C21 C22 . . . . 0.9(7) ?
C20 C21 C22 C23 . . . . 0.9(8) ?
C20 C21 C22 F1 . . . . -179.0(4) ?
C21 C22 C23 C24 . . . . -1.4(7) ?
F1 C22 C23 C24 . . . . 178.5(4) ?
C20 C19 C24 C23 . . . . 1.6(5) ?
C7 C19 C24 C23 . . . . -175.4(3) ?
C22 C23 C24 C19 . . . . 0.2(6) ?
