#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:41:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178438 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/59/4025921.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_4025921
loop_
_publ_author_name
'Adam Duong'
'Thierry Maris'
'Olivier Lebel'
'James D. Wuest'
_publ_section_title
;
 Syntheses and Structures of Isomeric Diaminotriazinyl-Substituted
 2,2'-Bipyridines and 1,10-Phenanthrolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1333
_journal_page_last               1341
_journal_paper_doi               10.1021/jo102191n
_journal_volume                  76
_journal_year                    2011
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C16 H15 N12, 6(C2 H F3 O2), C2 F3 O2'
_chemical_formula_sum            'C30 H21 F21 N12 O14'
_chemical_formula_weight         1172.59
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 119.062(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1219(19)
_cell_length_b                   15.1818(15)
_cell_length_c                   17.9876(16)
_cell_measurement_reflns_used    17068
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.77
_cell_measurement_theta_min      4.05
_cell_volume                     4325.7(8)
_computing_cell_refinement       'SAINT V7.34A(Bruker AXS, 2006)'
_computing_data_collection       'APEX2  (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A(Bruker AXS, 2006)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.9999
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.072
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            66802
_diffrn_reflns_theta_full        68.59
_diffrn_reflns_theta_max         68.59
_diffrn_reflns_theta_min         4.03
_exptl_absorpt_coefficient_mu    1.803
_exptl_absorpt_correction_T_max  0.8657
_exptl_absorpt_correction_T_min  0.5441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2344
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     652
_refine_ls_number_reflns         7988
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0698
_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)+(0.1074P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1721
_reflns_number_gt                5352
_reflns_number_total             7988
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            COD_J_Org_Chem_76_2011_1333_1341.cif
_cod_data_source_block           jw1227
_cod_original_cell_volume        4325.7(7)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4025921
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.58818(18) 0.85853(17) 0.82307(15) 0.0529(6) Uani 1 1 d U . .
N2 N 0.34559(17) 0.90374(16) 0.53660(14) 0.0471(5) Uani 1 1 d U . .
N3 N 0.32724(17) 0.91907(16) 0.39971(14) 0.0467(5) Uani 1 1 d U . .
H3 H 0.2935 0.9272 0.3449 0.056 Uiso 1 1 calc R . .
N4 N 0.46317(16) 0.90258(15) 0.51301(13) 0.0432(5) Uani 1 1 d U . .
N5 N 0.21405(17) 0.91607(17) 0.42101(15) 0.0530(6) Uani 1 1 d U . .
H5A H 0.1911 0.9123 0.4542 0.064 Uiso 1 1 calc R . .
H5B H 0.1818 0.9221 0.3657 0.064 Uiso 1 1 calc R . .
N6 N 0.44083(16) 0.91532(15) 0.37703(13) 0.0447(5) Uani 1 1 d U . .
H6A H 0.4955 0.9102 0.3961 0.054 Uiso 1 1 calc R . .
H6B H 0.4063 0.9221 0.3222 0.054 Uiso 1 1 calc R . .
N7 N 0.74951(16) 0.84245(14) 0.89868(13) 0.0414(5) Uani 1 1 d U . .
N8 N 0.86810(16) 0.85167(14) 0.70064(14) 0.0429(5) Uani 1 1 d U . .
N9 N 1.00303(16) 0.82743(15) 0.71683(14) 0.0443(5) Uani 1 1 d U . .
N10 N 0.98439(16) 0.81522(16) 0.83561(15) 0.0484(5) Uani 1 1 d U . .
N11 N 0.89126(17) 0.86171(16) 0.58609(15) 0.0478(6) Uani 1 1 d U . .
H11A H 0.9252 0.8586 0.5641 0.057 Uiso 1 1 calc R . .
H11B H 0.8376 0.8746 0.5535 0.057 Uiso 1 1 calc R . .
N12 N 1.11225(19) 0.7907(2) 0.84705(17) 0.0659(8) Uani 1 1 d U . .
H12A H 1.1463 0.7879 0.8251 0.079 Uiso 1 1 calc R . .
H12B H 1.1318 0.7799 0.9015 0.079 Uiso 1 1 calc R . .
C1 C 0.6208(2) 0.86363(18) 0.77056(16) 0.0427(5) Uani 1 1 d U . .
C2 C 0.5698(2) 0.87656(18) 0.68424(17) 0.0437(5) Uani 1 1 d U . .
H2 H 0.5927 0.8794 0.6467 0.052 Uiso 1 1 calc R . .
C3 C 0.48433(19) 0.88521(17) 0.65474(16) 0.0405(5) Uani 1 1 d U . .
C4 C 0.4525(2) 0.8795(2) 0.70951(18) 0.0523(7) Uani 1 1 d U . .
H4 H 0.3934 0.8825 0.6893 0.063 Uiso 1 1 calc R . .
C5 C 0.5080(2) 0.8693(2) 0.79424(19) 0.0569(7) Uani 1 1 d U . .
H5 H 0.4869 0.8701 0.8334 0.068 Uiso 1 1 calc R . .
C6 C 0.42765(19) 0.89865(17) 0.56179(17) 0.0422(5) Uani 1 1 d U . .
C7 C 0.2948(2) 0.91280(18) 0.45336(17) 0.0445(5) Uani 1 1 d U . .
C8 C 0.4108(2) 0.91282(18) 0.43025(17) 0.0453(5) Uani 1 1 d U . .
C9 C 0.71387(19) 0.85333(17) 0.81322(15) 0.0404(5) Uani 1 1 d U . .
C10 C 0.76270(18) 0.85183(16) 0.77321(16) 0.0378(5) Uani 1 1 d U . .
H10 H 0.7377 0.8600 0.7135 0.045 Uiso 1 1 calc R . .
C11 C 0.8314(2) 0.82838(18) 0.94532(17) 0.0456(6) Uani 1 1 d U . .
H11 H 0.8547 0.8195 1.0048 0.055 Uiso 1 1 calc R . .
C12 C 0.8839(2) 0.82622(17) 0.91013(17) 0.0428(5) Uani 1 1 d U . .
H12 H 0.9428 0.8168 0.9446 0.051 Uiso 1 1 calc R . .
C13 C 0.84810(19) 0.83823(17) 0.82202(16) 0.0410(5) Uani 1 1 d U . .
C14 C 0.90263(19) 0.83522(17) 0.78197(16) 0.0417(5) Uani 1 1 d U . .
C15 C 1.0340(2) 0.8108(2) 0.79955(18) 0.0484(6) Uani 1 1 d U . .
C16 C 0.92025(19) 0.84735(16) 0.66631(17) 0.0411(5) Uani 1 1 d U . .
O1 O 1.12729(13) 0.85284(14) 0.51733(13) 0.0576(5) Uani 1 1 d DU . .
H1 H 1.1557 0.8296 0.5654 0.086 Uiso 1 1 calc R . .
O2 O 1.01742(15) 0.83332(13) 0.53936(13) 0.0527(5) Uani 1 1 d U . .
C20 C 1.05018(15) 0.85633(18) 0.49886(18) 0.0482(5) Uani 1 1 d DU . .
C21 C 0.9963(2) 0.89892(18) 0.41203(19) 0.0492(5) Uani 1 1 d U . .
F1 F 1.02417(13) 0.88303(14) 0.35682(11) 0.0679(5) Uani 1 1 d U . .
F2 F 0.91703(14) 0.87010(13) 0.37254(13) 0.0707(5) Uani 1 1 d U . .
F3 F 0.99075(17) 0.98452(11) 0.41830(12) 0.0779(6) Uani 1 1 d U . .
O3 O 0.71291(16) 0.88718(17) 0.48521(13) 0.0654(6) Uani 1 1 d U . .
O4 O 0.59035(15) 0.89598(19) 0.36479(14) 0.0749(7) Uani 1 1 d DU . .
H4A H 0.5774 0.8836 0.3144 0.112 Uiso 1 1 calc R . .
C22 C 0.7149(2) 0.92192(19) 0.35908(19) 0.0514(5) Uani 1 1 d U . .
C23 C 0.67009(15) 0.9013(2) 0.40957(17) 0.0558(6) Uani 1 1 d DU . .
F4 F 0.78261(14) 0.97147(13) 0.40656(13) 0.0707(5) Uani 1 1 d U . .
F5 F 0.74247(14) 0.84939(11) 0.34005(12) 0.0632(5) Uani 1 1 d U . .
F6 F 0.66973(14) 0.96582(12) 0.28795(11) 0.0667(5) Uani 1 1 d U . .
O5 O -0.07408(18) 0.84832(14) 0.16153(14) 0.0738(7) Uani 1 1 d U . .
O6 O -0.02614(17) 0.98515(14) 0.19438(16) 0.0748(7) Uani 1 1 d DU . .
H6 H 0.0182 0.9643 0.1976 0.112 Uiso 1 1 calc R . .
C24 C -0.1653(3) 0.9575(3) 0.1688(4) 0.0962(8) Uani 1 1 d U . .
C25 C -0.0801(2) 0.92394(18) 0.1762(2) 0.0624(6) Uani 1 1 d DU . .
F7 F -0.1506(2) 1.01548(19) 0.2284(2) 0.1264(9) Uani 1 1 d U . .
F8 F -0.2026(2) 0.8924(2) 0.1809(3) 0.1359(11) Uani 1 1 d U . .
F9 F -0.20975(19) 0.9922(2) 0.0960(2) 0.1418(12) Uani 1 1 d U . .
O7 O 0.24169(17) 0.90713(17) 0.23320(14) 0.0740(7) Uani 1 1 d DU . .
O8 O 0.12405(17) 0.93639(16) 0.23779(15) 0.0706(6) Uani 1 1 d U . .
C26 C 0.1177(3) 0.9151(2) 0.1022(2) 0.0682(6) Uani 1 1 d U . .
C27 C 0.16239(17) 0.9189(2) 0.1984(2) 0.0614(7) Uani 1 1 d DU . .
F10 F 0.12642(19) 0.83910(13) 0.07298(12) 0.0960(8) Uani 1 1 d U . .
F11 F 0.14348(19) 0.97390(14) 0.06830(13) 0.0929(7) Uani 1 1 d U . .
F12 F 0.03755(19) 0.9328(2) 0.07146(14) 0.1205(9) Uani 1 1 d U . .
O9 O 1.24037(15) 0.82840(15) 0.66196(13) 0.0610(6) Uani 1 1 d U . .
O10 O 1.16103(14) 0.79518(17) 0.72249(13) 0.0663(6) Uani 1 1 d DU . .
H10A H 1.1220 0.7970 0.6718 0.099 Uiso 1 1 calc . . .
C28 C 1.3083(2) 0.8102(2) 0.8094(2) 0.0563(5) Uani 1 1 d U . .
C29 C 1.23096(16) 0.8118(2) 0.72510(18) 0.0526(6) Uani 1 1 d DU . .
F13 F 1.29440(13) 0.77964(14) 0.87093(11) 0.0740(6) Uani 1 1 d U . .
F14 F 1.34197(13) 0.88942(12) 0.83073(11) 0.0655(5) Uani 1 1 d U . .
F15 F 1.36718(13) 0.75781(12) 0.80628(13) 0.0704(5) Uani 1 1 d U . .
O11 O 0.3931(2) 0.9408(2) 0.2018(2) 0.1073(10) Uani 1 1 d U . .
O12 O 0.4931(2) 0.8537(3) 0.2029(2) 0.1397(16) Uani 1 1 d DU . .
H12C H 0.5026 0.8407 0.1630 0.210 Uiso 1 1 calc R . .
C30 C 0.4224(2) 0.8929(2) 0.1732(2) 0.0725(8) Uani 1 1 d DU . .
C31 C 0.3627(5) 0.8765(3) 0.0780(3) 0.1111(11) Uani 1 1 d U . .
F16 F 0.3851(2) 0.9246(2) 0.02813(16) 0.1333(11) Uani 1 1 d U . .
F17 F 0.2826(3) 0.8948(4) 0.0489(2) 0.2047(19) Uani 1 1 d U . .
F18 F 0.3659(4) 0.7931(2) 0.05832(19) 0.270(3) Uani 1 1 d U . .
O13 O 0.6547(4) 0.8063(3) -0.0159(3) 0.1138(17) Uiso 0.721(6) 1 d PU A 1
O14 O 0.64574(13) 0.69296(12) 0.05783(12) 0.113(3) Uiso 0.721(6) 1 d PU A 1
H14 H 0.6716 0.6656 0.0369 0.169 Uiso 0.721(6) 1 calc PR A 1
C32 C 0.64060(13) 0.77021(12) 0.03869(12) 0.112(3) Uiso 0.721(6) 1 d PRU A 1
C33 C 0.59479(13) 0.83088(12) 0.07186(12) 0.098(2) Uiso 0.721(6) 1 d PRU A 1
F19 F 0.61987(13) 0.81509(12) 0.15412(12) 0.1264(19) Uiso 0.721(6) 1 d PRU A 1
F20 F 0.60590(13) 0.91479(12) 0.06608(12) 0.153(3) Uiso 0.721(6) 1 d PRU A 1
F21 F 0.51279(13) 0.81398(12) 0.03140(12) 0.181(3) Uiso 0.721(6) 1 d PRU A 1
O13B O 0.63585(13) 0.80622(12) 0.16476(12) 0.036(2) Uiso 0.279(6) 1 d PRU A 2
O14B O 0.60058(13) 0.91849(12) 0.07511(12) 0.070(4) Uiso 0.279(6) 1 d PRU A 2
H14B H 0.5922 0.9442 0.1117 0.106 Uiso 0.279(6) 1 calc PR A 2
C32B C 0.62430(13) 0.84354(12) 0.09839(12) 0.087(5) Uiso 0.279(6) 1 d PRU A 2
C33B C 0.64286(13) 0.78600(12) 0.03931(12) 0.042(3) Uiso 0.279(6) 1 d PRU A 2
F19B F 0.65449(13) 0.70133(12) 0.06345(12) 0.165(11) Uiso 0.279(6) 1 d PRU A 2
F20B F 0.70904(13) 0.80851(12) 0.03332(12) 0.114(4) Uiso 0.279(6) 1 d PRU A 2
F21B F 0.57658(13) 0.78601(12) -0.03801(12) 0.146(5) Uiso 0.279(6) 1 d PRU A 2
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'
F F 0.0727 0.0534 '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_publ_flag
C5 N1 C1 120.3(3) y
C6 N2 C7 115.9(2) y
C8 N3 C7 119.9(2) y
C8 N3 H3 120.1 ?
C7 N3 H3 120.1 ?
C6 N4 C8 115.9(3) y
C7 N5 H5A 120.0 ?
C7 N5 H5B 120.0 ?
H5A N5 H5B 120.0 ?
C8 N6 H6A 120.0 ?
C8 N6 H6B 120.0 ?
H6A N6 H6B 120.0 ?
C11 N7 C9 120.6(2) y
C14 N8 C16 116.1(3) y
C15 N9 C16 121.2(2) y
C15 N10 C14 115.2(2) y
C16 N11 H11A 120.0 ?
C16 N11 H11B 120.0 ?
H11A N11 H11B 120.0 ?
C15 N12 H12A 120.0 ?
C15 N12 H12B 120.0 ?
H12A N12 H12B 120.0 ?
N1 C1 C2 121.2(3) y
N1 C1 C9 114.2(2) y
C2 C1 C9 124.6(2) y
C3 C2 C1 117.4(3) y
C3 C2 H2 121.3 ?
C1 C2 H2 121.3 ?
C4 C3 C2 120.4(3) y
C4 C3 C6 121.0(3) y
C2 C3 C6 118.6(2) y
C3 C4 C5 118.2(3) y
C3 C4 H4 120.9 ?
C5 C4 H4 120.9 ?
N1 C5 C4 122.4(3) y
N1 C5 H5 118.8 ?
C4 C5 H5 118.8 ?
N4 C6 N2 126.7(2) y
N4 C6 C3 117.4(3) y
N2 C6 C3 115.9(2) y
N5 C7 N2 121.7(3) y
N5 C7 N3 117.8(2) y
N2 C7 N3 120.4(3) y
N6 C8 N4 119.9(3) y
N6 C8 N3 119.0(2) y
N4 C8 N3 121.1(2) y
N7 C9 C10 120.9(3) y
N7 C9 C1 113.2(2) y
C10 C9 C1 125.8(2) y
C13 C10 C9 118.4(2) y
C13 C10 H10 120.8 ?
C9 C10 H10 120.8 ?
N7 C11 C12 121.8(2) y
N7 C11 H11 119.1 ?
C12 C11 H11 119.1 ?
C11 C12 C13 118.3(3) y
C11 C12 H12 120.9 ?
C13 C12 H12 120.9 ?
C10 C13 C12 120.0(3) y
C10 C13 C14 120.3(2) y
C12 C13 C14 119.7(3) y
N8 C14 N10 127.2(3) y
N8 C14 C13 118.0(3) y
N10 C14 C13 114.8(2) y
N12 C15 N9 121.0(3) y
N12 C15 N10 118.2(3) y
N9 C15 N10 120.8(3) y
N11 C16 N9 120.2(3) y
N11 C16 N8 120.3(3) y
N9 C16 N8 119.5(2) y
C20 O1 H1 109.5 ?
O2 C20 O1 129.6(3) y
O2 C20 C21 119.2(2) y
O1 C20 C21 111.2(2) y
F3 C21 F2 105.3(3) y
F3 C21 F1 108.3(2) y
F2 C21 F1 104.1(2) y
F3 C21 C20 111.7(2) y
F2 C21 C20 113.3(2) y
F1 C21 C20 113.5(3) y
C23 O4 H4A 109.5 ?
F6 C22 F5 107.8(2) y
F6 C22 F4 106.3(2) y
F5 C22 F4 106.9(3) y
F6 C22 C23 115.1(3) y
F5 C22 C23 111.3(2) y
F4 C22 C23 109.0(2) y
O3 C23 O4 127.6(3) y
O3 C23 C22 118.1(2) y
O4 C23 C22 114.1(2) y
C25 O6 H6 109.5 ?
F9 C24 F8 112.0(5) y
F9 C24 F7 109.8(4) y
F8 C24 F7 107.2(5) y
F9 C24 C25 109.1(4) y
F8 C24 C25 108.4(3) y
F7 C24 C25 110.4(4) y
O5 C25 O6 128.2(3) y
O5 C25 C24 119.0(3) y
O6 C25 C24 112.8(3) y
F11 C26 F12 103.9(3) y
F11 C26 F10 106.1(3) y
F12 C26 F10 109.7(3) y
F11 C26 C27 113.4(3) y
F12 C26 C27 110.2(3) y
F10 C26 C27 113.0(3) y
O8 C27 O7 124.2(3) y
O8 C27 C26 121.6(3) y
O7 C27 C26 114.1(3) y
C29 O10 H10A 109.5 ?
F14 C28 F13 108.9(3) y
F14 C28 F15 106.5(3) y
F13 C28 F15 107.4(2) y
F14 C28 C29 111.0(2) y
F13 C28 C29 112.9(3) y
F15 C28 C29 109.8(3) y
O9 C29 O10 125.4(3) y
O9 C29 C28 116.9(2) y
O10 C29 C28 117.7(3) y
C30 O12 H12C 109.5 ?
O11 C30 O12 133.9(4) y
O11 C30 C31 111.7(4) y
O12 C30 C31 114.4(4) y
F17 C31 F18 106.3(6) y
F17 C31 F16 104.4(4) y
F18 C31 F16 105.7(5) y
F17 C31 C30 117.0(5) y
F18 C31 C30 110.7(4) y
F16 C31 C30 111.9(5) y
C32 O14 H14 109.5 ?
O14 C32 O13 128.9(3) y
O14 C32 C33 116.7 y
O13 C32 C33 113.3(3) y
F20 C33 F21 108.8 y
F20 C33 F19 106.3 y
F21 C33 F19 105.1 y
F20 C33 C32 114.9 y
F21 C33 C32 110.1 y
F19 C33 C32 111.3 y
C32B O14B H14B 109.5 ?
O14B C32B O13B 128.5 y
O14B C32B C33B 117.0 y
O13B C32B C33B 114.5 y
F20B C33B F21B 108.4 y
F20B C33B F19B 105.8 y
F21B C33B F19B 105.1 y
F20B C33B C32B 115.4 y
F21B C33B C32B 109.6 y
F19B C33B C32B 112.0 y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 1.294(4) y
N1 C1 1.338(4) y
N2 C6 1.330(4) y
N2 C7 1.330(4) y
N3 C8 1.341(4) y
N3 C7 1.355(4) y
N3 H3 0.8800 ?
N4 C6 1.318(3) y
N4 C8 1.330(4) y
N5 C7 1.287(4) y
N5 H5a 0.8800 ?
N5 H5b 0.8800 ?
N6 C8 1.311(4) y
N6 H6a 0.8800 ?
N6 H6b 0.8800 ?
N7 C11 1.319(4) y
N7 C9 1.358(3) y
N8 C14 1.306(3) y
N8 C16 1.359(4) y
N9 C15 1.335(4) y
N9 C16 1.358(4) y
N10 C15 1.341(4) y
N10 C14 1.353(4) y
N11 C16 1.292(4) y
N11 H11a 0.8800 ?
N11 H11b 0.8800 ?
N12 C15 1.288(4) y
N12 H12a 0.8800 ?
N12 H12b 0.8800 ?
C1 C2 1.382(4) y
C1 C9 1.483(4) y
C2 C3 1.378(4) y
C2 H2 0.9500 ?
C3 C4 1.365(4) y
C3 C6 1.491(4) y
C4 C5 1.367(4) y
C4 H4 0.9500 ?
C5 H5 0.9500 ?
C9 C10 1.386(4) y
C10 C13 1.374(4) y
C10 H10 0.9500 ?
C11 C12 1.375(4) y
C11 H11 0.9500 ?
C12 C13 1.403(4) y
C12 H12 0.9500 ?
C13 C14 1.479(4) y
O1 C20 1.271(4) y
O1 H1 0.8400 ?
O2 C20 1.194(3) y
C20 C21 1.526(4) y
C21 F3 1.312(3) y
C21 F2 1.329(4) y
C21 F1 1.337(3) y
O3 C23 1.214(3) y
O4 C23 1.270(3) y
O4 H4a 0.8400 ?
C22 F6 1.317(3) y
C22 F5 1.321(3) y
C22 F4 1.335(4) y
C22 C23 1.517(4) y
O5 C25 1.195(4) y
O6 C25 1.271(4) y
O6 H6 0.8400 ?
C24 F9 1.271(6) y
C24 F8 1.273(5) y
C24 F7 1.311(6) y
C24 C25 1.569(6) y
O7 C27 1.271(4) y
O8 C27 1.239(4) y
C26 F11 1.291(4) y
C26 F12 1.306(5) y
C26 F10 1.309(4) y
C26 C27 1.513(5) y
O9 C29 1.253(3) y
O10 C29 1.271(4) y
O10 H10a 0.8400 ?
C28 F14 1.318(4) y
C28 F13 1.332(3) y
C28 F15 1.354(4) y
C28 C29 1.482(4) y
O11 C30 1.158(4) y
O12 C30 1.271(4) y
O12 H12c 0.8400 ?
C30 C31 1.538(6) y
C31 F17 1.311(8) y
C31 F18 1.324(6) y
C31 F16 1.363(6) y
O13 C32 1.254(5) y
O14 C32 1.2130 y
O14 H14 0.8400 ?
C32 C33 1.5412 y
C33 F20 1.3018 y
C33 F21 1.3240 y
C33 F19 1.3416 y
O13b C32b 1.2439 y
O14b C32b 1.2165 y
O14b H14b 0.8400 ?
C32b C33b 1.5338 y
C33b F20b 1.3009 y
C33b F21b 1.3244 y
C33b F19b 1.3404 y
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
N5 H5A O1 0.88 2.17 3.007(3) 158.3 1_455
N5 H5B O8 0.88 2.02 2.897(3) 171.4 .
N6 H6A O4 0.88 2.06 2.838(3) 146.3 .
N6 H6B O11 0.88 2.08 2.861(4) 147.4 .
N6 H6B O7 0.88 2.62 3.265(4) 130.8 .
N11 H11A O2 0.88 1.96 2.826(3) 165.9 .
N11 H11B O3 0.88 1.99 2.862(4) 171.7 .
N12 H12A O10 0.88 1.99 2.780(3) 148.4 .
O1 H1 O9 0.84 1.67 2.434(3) 150.6 .
O4 H4A O12 0.84 1.89 2.648(4) 148.7 .
O6 H6 O8 0.84 1.74 2.550(4) 160.9 .
N3 H3 O7 0.88 1.78 2.626(3) 159.5 .
O10 H10A O2 0.84 2.28 3.103(3) 167.8 .
O12 H12C O13B 0.84 2.46 3.068(4) 130.4 .
O14 H14 O3 0.84 1.66 2.493(3) 173.6 4_575
