#------------------------------------------------------------------------------
#$Date: 2017-02-04 04:26:12 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191389 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/51/1545138.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_1545138
loop_
_publ_author_name
'Kong, Jiahui'
'Shao, Jiewei'
'Li, Chengjie'
'Qi, Dongdong'
'Li, Minzhi'
'Liang, Xu'
'Zhu, Weihua'
'Jiang, Jianzhuang'
'Xie, Yongshu'
_publ_section_title
;
 Neo-N-confused Phlorins and Phlorinone: Rational Synthesis and Tunable
 Properties.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              650
_journal_page_last               653
_journal_paper_doi               10.1021/acs.orglett.6b03816
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C59 H39 F15 N4'
_chemical_formula_weight         1088.94
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                119.469(3)
_cell_angle_beta                 93.1170(10)
_cell_angle_gamma                105.428(2)
_cell_formula_units_Z            2
_cell_length_a                   13.8688(12)
_cell_length_b                   15.3205(13)
_cell_length_c                   15.3261(15)
_cell_measurement_temperature    298(2)
_cell_volume                     2665.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0812
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12936
_diffrn_reflns_theta_full        24.50
_diffrn_reflns_theta_max         24.50
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9771
_exptl_absorpt_correction_T_min  0.9494
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     706
_refine_ls_number_reflns         8713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.0834
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1651P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2294
_refine_ls_wR_factor_ref         0.2746
_reflns_number_gt                4238
_reflns_number_total             8713
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03816_si_002.cif
_cod_data_source_block           160118f
_cod_depositor_comments
'Adding full bibliography for 1545137--1545139.cif.'
_cod_database_code               1545138
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.2874(3) 0.0959(3) 0.3308(3) 0.1238(15) Uani 1 1 d .
F2 F 0.2372(4) -0.1140(4) 0.1868(3) 0.1516(19) Uani 1 1 d .
F3 F 0.0395(3) -0.2407(3) 0.1091(2) 0.1179(13) Uani 1 1 d .
F4 F -0.1119(3) -0.1563(3) 0.1757(3) 0.1225(14) Uani 1 1 d .
F5 F -0.0629(2) 0.0530(3) 0.3183(3) 0.1044(11) Uani 1 1 d .
F6 F 0.4472(3) 0.3976(3) 0.8075(3) 0.1169(13) Uani 1 1 d .
F7 F 0.5096(4) 0.3525(4) 0.9465(4) 0.173(2) Uani 1 1 d .
F8 F 0.3879(5) 0.3372(3) 1.0766(3) 0.176(2) Uani 1 1 d .
F9 F 0.2011(5) 0.3645(3) 1.0638(3) 0.155(2) Uani 1 1 d .
F10 F 0.1432(3) 0.4136(3) 0.9276(2) 0.0973(11) Uani 1 1 d .
F11 F 0.0731(2) 0.7734(2) 0.9269(2) 0.0719(8) Uani 1 1 d .
F12 F 0.0689(3) 0.9716(3) 1.0468(2) 0.0880(10) Uani 1 1 d .
F13 F 0.1732(3) 1.1319(2) 1.0198(2) 0.1094(12) Uani 1 1 d .
F14 F 0.2854(3) 1.0907(3) 0.8715(3) 0.1128(12) Uani 1 1 d .
F15 F 0.2938(3) 0.8941(2) 0.7527(2) 0.0914(10) Uani 1 1 d .
N1 N 0.1783(3) 0.3732(3) 0.4171(3) 0.0486(9) Uani 1 1 d .
H1 H 0.1969 0.4134 0.4829 0.058 Uiso 1 1 calc R
N2 N 0.1950(3) 0.3418(3) 0.5942(2) 0.0464(8) Uani 1 1 d .
N3 N 0.2192(3) 0.5583(3) 0.7506(3) 0.0513(9) Uani 1 1 d .
H3 H 0.1999 0.5183 0.6848 0.062 Uiso 1 1 calc R
N4 N 0.1019(3) 0.6251(3) 0.4945(3) 0.0576(10) Uani 1 1 d .
H4 H 0.0629 0.6176 0.4440 0.069 Uiso 1 1 calc R
C1 C 0.1755(3) 0.4096(3) 0.3499(3) 0.0505(11) Uani 1 1 d .
C2 C 0.1397(4) 0.3194(4) 0.2513(3) 0.0607(12) Uani 1 1 d .
H2 H 0.1294 0.3196 0.1909 0.073 Uiso 1 1 calc R
C3 C 0.1214(4) 0.2278(4) 0.2575(3) 0.0600(12) Uani 1 1 d .
H3A H 0.0972 0.1577 0.2025 0.072 Uiso 1 1 calc R
C4 C 0.1464(3) 0.2621(3) 0.3622(3) 0.0488(10) Uani 1 1 d .
C5 C 0.1421(3) 0.2000(3) 0.4078(3) 0.0496(11) Uani 1 1 d .
C6 C 0.1651(3) 0.2353(3) 0.5120(3) 0.0508(11) Uani 1 1 d .
C7 C 0.1704(4) 0.1640(4) 0.5493(3) 0.0617(13) Uani 1 1 d .
H7 H 0.1524 0.0902 0.5105 0.074 Uiso 1 1 calc R
C8 C 0.2071(4) 0.2286(4) 0.6520(3) 0.0632(13) Uani 1 1 d .
H8 H 0.2211 0.2077 0.6975 0.076 Uiso 1 1 calc R
C9 C 0.2206(3) 0.3377(3) 0.6784(3) 0.0500(11) Uani 1 1 d .
C10 C 0.2562(3) 0.4268(3) 0.7826(3) 0.0508(11) Uani 1 1 d .
C11 C 0.2546(3) 0.5281(4) 0.8145(3) 0.0536(11) Uani 1 1 d .
C12 C 0.2809(4) 0.6221(4) 0.9188(3) 0.0600(12) Uani 1 1 d .
H12 H 0.3086 0.6267 0.9781 0.072 Uiso 1 1 calc R
C13 C 0.2583(4) 0.7012(4) 0.9152(3) 0.0583(12) Uani 1 1 d .
H13 H 0.2665 0.7682 0.9714 0.070 Uiso 1 1 calc R
C14 C 0.2192(3) 0.6632(3) 0.8082(3) 0.0512(11) Uani 1 1 d .
C15 C 0.1891(3) 0.7163(3) 0.7671(3) 0.0520(11) Uani 1 1 d .
C16 C 0.0933(4) 0.6761(4) 0.5960(3) 0.0599(12) Uani 1 1 d .
H16 H 0.0451 0.7091 0.6207 0.072 Uiso 1 1 calc R
C17 C 0.1667(3) 0.6702(3) 0.6541(3) 0.0498(11) Uani 1 1 d .
C18 C 0.2234(3) 0.6129(4) 0.5847(3) 0.0529(11) Uani 1 1 d .
H18 H 0.2776 0.5953 0.6018 0.063 Uiso 1 1 calc R
C19 C 0.1829(3) 0.5886(4) 0.4880(3) 0.0504(11) Uani 1 1 d .
C20 C 0.2177(3) 0.5264(3) 0.3873(3) 0.0498(11) Uani 1 1 d .
C21 C 0.1142(4) 0.0807(3) 0.3299(3) 0.0506(11) Uani 1 1 d .
C22 C 0.1883(4) 0.0359(4) 0.2949(4) 0.0732(15) Uani 1 1 d .
C23 C 0.1628(5) -0.0736(5) 0.2201(4) 0.0827(17) Uani 1 1 d .
C24 C 0.0630(6) -0.1351(4) 0.1817(4) 0.0764(16) Uani 1 1 d .
C25 C -0.0119(5) -0.0936(4) 0.2156(4) 0.0759(16) Uani 1 1 d .
C26 C 0.0141(4) 0.0146(4) 0.2890(4) 0.0648(13) Uani 1 1 d .
C27 C 0.2942(4) 0.4078(4) 0.8633(3) 0.0620(13) Uani 1 1 d .
C28 C 0.3839(5) 0.3909(4) 0.8715(4) 0.0770(16) Uani 1 1 d .
C29 C 0.4183(7) 0.3663(5) 0.9425(6) 0.104(2) Uani 1 1 d .
C30 C 0.3556(8) 0.3605(5) 1.0084(5) 0.106(3) Uani 1 1 d .
C31 C 0.2664(7) 0.3749(5) 1.0023(4) 0.095(2) Uani 1 1 d .
C32 C 0.2328(5) 0.3985(4) 0.9317(4) 0.0734(16) Uani 1 1 d .
C33 C 0.1826(3) 0.8243(3) 0.8335(3) 0.0513(11) Uani 1 1 d .
C34 C 0.1272(4) 0.8497(4) 0.9110(3) 0.0589(12) Uani 1 1 d .
C35 C 0.1237(4) 0.9515(4) 0.9730(3) 0.0623(13) Uani 1 1 d .
C36 C 0.1752(5) 1.0319(4) 0.9591(4) 0.0727(15) Uani 1 1 d .
C37 C 0.2323(5) 1.0117(4) 0.8842(4) 0.0755(15) Uani 1 1 d .
C38 C 0.2346(4) 0.9085(4) 0.8220(3) 0.0641(13) Uani 1 1 d .
C39 C 0.1750(4) 0.5466(4) 0.3038(3) 0.0531(11) Uani 1 1 d .
C40 C 0.0681(4) 0.5024(4) 0.2608(3) 0.0622(13) Uani 1 1 d .
H40 H 0.0248 0.4643 0.2837 0.075 Uiso 1 1 calc R
C41 C 0.0273(4) 0.5155(5) 0.1850(4) 0.0732(15) Uani 1 1 d .
H41 H -0.0427 0.4850 0.1563 0.088 Uiso 1 1 calc R
C42 C 0.0917(5) 0.5742(5) 0.1524(4) 0.0761(15) Uani 1 1 d .
H42 H 0.0645 0.5849 0.1031 0.091 Uiso 1 1 calc R
C43 C 0.1946(5) 0.6163(5) 0.1922(4) 0.0773(15) Uani 1 1 d .
H43 H 0.2372 0.6550 0.1693 0.093 Uiso 1 1 calc R
C44 C 0.2375(4) 0.6018(4) 0.2682(3) 0.0672(13) Uani 1 1 d .
H44 H 0.3080 0.6297 0.2939 0.081 Uiso 1 1 calc R
C45 C 0.3363(4) 0.5657(4) 0.4106(3) 0.0600(12) Uani 1 1 d .
C46 C 0.3887(4) 0.4967(5) 0.3652(5) 0.0885(17) Uani 1 1 d .
H46 H 0.3526 0.4245 0.3208 0.106 Uiso 1 1 calc R
C47 C 0.4972(6) 0.5337(8) 0.3848(6) 0.122(3) Uani 1 1 d .
H47 H 0.5326 0.4865 0.3539 0.146 Uiso 1 1 calc R
C48 C 0.5485(6) 0.6393(8) 0.4495(6) 0.126(3) Uani 1 1 d .
H48 H 0.6198 0.6637 0.4635 0.151 Uiso 1 1 calc R
C49 C 0.4984(5) 0.7112(7) 0.4950(5) 0.106(2) Uani 1 1 d .
H49 H 0.5353 0.7834 0.5379 0.128 Uiso 1 1 calc R
C50 C 0.3919(4) 0.6747(5) 0.4761(4) 0.0784(16) Uani 1 1 d .
H50 H 0.3573 0.7227 0.5069 0.094 Uiso 1 1 calc R
C51 C 0.1028(9) 0.8346(8) 0.4229(6) 0.143(3) Uani 1 1 d .
H51A H 0.0702 0.7934 0.4509 0.214 Uiso 1 1 calc R
H51B H 0.0857 0.7910 0.3492 0.214 Uiso 1 1 calc R
H51C H 0.0793 0.8942 0.4445 0.214 Uiso 1 1 calc R
C52 C 0.2165(15) 0.8739(14) 0.4605(14) 0.247(8) Uani 1 1 d .
H52A H 0.2315 0.8140 0.4567 0.296 Uiso 1 1 calc R
H52B H 0.2446 0.8824 0.4074 0.296 Uiso 1 1 calc R
C53 C 0.2759(14) 0.9578(14) 0.5478(12) 0.213(6) Uani 1 1 d .
H53A H 0.2469 0.9511 0.6013 0.255 Uiso 1 1 calc R
H53B H 0.2636 1.0185 0.5507 0.255 Uiso 1 1 calc R
C54 C 0.3902(15) 0.9924(15) 0.5838(14) 0.242(7) Uani 1 1 d .
H54A H 0.4050 0.9413 0.5975 0.290 Uiso 1 1 calc R
H54B H 0.4223 0.9901 0.5284 0.290 Uiso 1 1 calc R
C55 C 0.4371(15) 1.0985(16) 0.6755(14) 0.255(7) Uani 1 1 d .
H55A H 0.4276 1.1488 0.6577 0.306 Uiso 1 1 calc R
H55B H 0.3972 1.1024 0.7266 0.306 Uiso 1 1 calc R
C56 C 0.5422(14) 1.1372(17) 0.7251(17) 0.344(13) Uani 1 1 d .
H56A H 0.5697 1.0800 0.6964 0.515 Uiso 1 1 calc R
H56B H 0.5478 1.1649 0.7973 0.515 Uiso 1 1 calc R
H56C H 0.5800 1.1927 0.7150 0.515 Uiso 1 1 calc R
C57 C 0.4698(18) 0.1999(19) 0.1950(15) 0.329(12) Uani 1 1 d .
H57A H 0.5273 0.2221 0.2477 0.493 Uiso 1 1 calc R
H57B H 0.4130 0.2150 0.2253 0.493 Uiso 1 1 calc R
H57C H 0.4880 0.2378 0.1603 0.493 Uiso 1 1 calc R
C58 C 0.440(2) 0.080(3) 0.1174(18) 0.353(17) Uani 1 1 d .
H58A H 0.4462 0.0441 0.1539 0.424 Uiso 1 1 calc R
H58B H 0.3683 0.0520 0.0823 0.424 Uiso 1 1 calc R
C59 C 0.504(3) 0.056(3) 0.0410(15) 0.32(2) Uani 1 1 d .
H59A H 0.5742 0.0911 0.0796 0.388 Uiso 1 1 calc R
H59B H 0.4933 0.0911 0.0054 0.388 Uiso 1 1 calc R
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C4 110.3(3) . .
C1 N1 H1 124.9 . .
C4 N1 H1 124.9 . .
C9 N2 C6 104.4(3) . .
C11 N3 C14 110.6(3) . .
C11 N3 H3 124.7 . .
C14 N3 H3 124.7 . .
C19 N4 C16 108.7(3) . .
C19 N4 H4 125.7 . .
C16 N4 H4 125.7 . .
C2 C1 N1 106.4(4) . .
C2 C1 C20 131.7(4) . .
N1 C1 C20 121.6(3) . .
C1 C2 C3 109.3(4) . .
C1 C2 H2 125.4 . .
C3 C2 H2 125.4 . .
C2 C3 C4 107.5(4) . .
C2 C3 H3A 126.3 . .
C4 C3 H3A 126.3 . .
N1 C4 C3 106.6(4) . .
N1 C4 C5 124.4(3) . .
C3 C4 C5 129.0(4) . .
C6 C5 C4 128.2(4) . .
C6 C5 C21 117.9(4) . .
C4 C5 C21 113.8(3) . .
C5 C6 N2 125.9(4) . .
C5 C6 C7 122.9(4) . .
N2 C6 C7 110.9(3) . .
C8 C7 C6 105.4(4) . .
C8 C7 H7 127.3 . .
C6 C7 H7 127.3 . .
C7 C8 C9 107.4(4) . .
C7 C8 H8 126.3 . .
C9 C8 H8 126.3 . .
N2 C9 C10 126.1(4) . .
N2 C9 C8 111.9(4) . .
C10 C9 C8 122.1(4) . .
C11 C10 C9 124.7(4) . .
C11 C10 C27 117.5(4) . .
C9 C10 C27 117.7(4) . .
C10 C11 N3 125.0(4) . .
C10 C11 C12 129.5(4) . .
N3 C11 C12 105.4(4) . .
C13 C12 C11 109.4(4) . .
C13 C12 H12 125.3 . .
C11 C12 H12 125.3 . .
C12 C13 C14 108.1(4) . .
C12 C13 H13 125.9 . .
C14 C13 H13 125.9 . .
C15 C14 N3 124.6(4) . .
C15 C14 C13 129.0(4) . .
N3 C14 C13 106.4(4) . .
C14 C15 C17 121.2(4) . .
C14 C15 C33 121.6(4) . .
C17 C15 C33 117.2(4) . .
C17 C16 N4 109.3(4) . .
C17 C16 H16 125.4 . .
N4 C16 H16 125.4 . .
C16 C17 C18 106.2(4) . .
C16 C17 C15 128.5(4) . .
C18 C17 C15 125.2(4) . .
C19 C18 C17 107.8(4) . .
C19 C18 H18 126.1 . .
C17 C18 H18 126.1 . .
N4 C19 C18 108.0(4) . .
N4 C19 C20 124.8(3) . .
C18 C19 C20 127.1(4) . .
C1 C20 C45 110.6(4) . .
C1 C20 C19 108.2(3) . .
C45 C20 C19 108.5(3) . .
C1 C20 C39 109.8(3) . .
C45 C20 C39 110.0(3) . .
C19 C20 C39 109.7(3) . .
C26 C21 C22 117.0(4) . .
C26 C21 C5 121.5(4) . .
C22 C21 C5 121.4(4) . .
F1 C22 C21 120.2(4) . .
F1 C22 C23 118.1(5) . .
C21 C22 C23 121.7(5) . .
F2 C23 C24 121.1(5) . .
F2 C23 C22 119.9(6) . .
C24 C23 C22 118.9(5) . .
C23 C24 C25 120.8(5) . .
C23 C24 F3 118.3(6) . .
C25 C24 F3 120.9(6) . .
C24 C25 F4 120.2(5) . .
C24 C25 C26 119.8(5) . .
F4 C25 C26 120.0(6) . .
F5 C26 C21 120.5(4) . .
F5 C26 C25 117.8(5) . .
C21 C26 C25 121.8(5) . .
C28 C27 C32 115.5(5) . .
C28 C27 C10 123.0(5) . .
C32 C27 C10 121.3(5) . .
C27 C28 F6 119.1(5) . .
C27 C28 C29 124.1(7) . .
F6 C28 C29 116.8(6) . .
F7 C29 C30 122.4(7) . .
F7 C29 C28 120.1(9) . .
C30 C29 C28 117.4(7) . .
C31 C30 F8 121.6(9) . .
C31 C30 C29 120.6(6) . .
F8 C30 C29 117.8(9) . .
C30 C31 F9 121.4(7) . .
C30 C31 C32 121.6(7) . .
F9 C31 C32 117.0(8) . .
F10 C32 C31 120.5(6) . .
F10 C32 C27 118.8(4) . .
C31 C32 C27 120.7(7) . .
C38 C33 C34 115.6(4) . .
C38 C33 C15 120.6(4) . .
C34 C33 C15 123.8(4) . .
F11 C34 C35 117.3(4) . .
F11 C34 C33 120.0(4) . .
C35 C34 C33 122.7(5) . .
F12 C35 C36 119.7(4) . .
F12 C35 C34 120.2(5) . .
C36 C35 C34 120.1(5) . .
F13 C36 C35 120.7(5) . .
F13 C36 C37 119.5(5) . .
C35 C36 C37 119.8(5) . .
F14 C37 C36 120.4(5) . .
F14 C37 C38 120.3(5) . .
C36 C37 C38 119.3(5) . .
F15 C38 C33 120.7(4) . .
F15 C38 C37 116.8(5) . .
C33 C38 C37 122.5(5) . .
C44 C39 C40 118.5(4) . .
C44 C39 C20 122.6(4) . .
C40 C39 C20 118.8(4) . .
C41 C40 C39 120.9(5) . .
C41 C40 H40 119.5 . .
C39 C40 H40 119.5 . .
C42 C41 C40 119.5(5) . .
C42 C41 H41 120.3 . .
C40 C41 H41 120.3 . .
C43 C42 C41 120.3(5) . .
C43 C42 H42 119.8 . .
C41 C42 H42 119.8 . .
C42 C43 C44 120.7(5) . .
C42 C43 H43 119.6 . .
C44 C43 H43 119.6 . .
C39 C44 C43 120.0(5) . .
C39 C44 H44 120.0 . .
C43 C44 H44 120.0 . .
C46 C45 C50 118.9(5) . .
C46 C45 C20 121.2(5) . .
C50 C45 C20 119.9(4) . .
C45 C46 C47 120.9(6) . .
C45 C46 H46 119.6 . .
C47 C46 H46 119.6 . .
C48 C47 C46 118.7(7) . .
C48 C47 H47 120.6 . .
C46 C47 H47 120.6 . .
C47 C48 C49 122.1(7) . .
C47 C48 H48 119.0 . .
C49 C48 H48 119.0 . .
C48 C49 C50 119.2(7) . .
C48 C49 H49 120.4 . .
C50 C49 H49 120.4 . .
C49 C50 C45 120.3(6) . .
C49 C50 H50 119.8 . .
C45 C50 H50 119.8 . .
C52 C51 H51A 109.5 . .
C52 C51 H51B 109.5 . .
H51A C51 H51B 109.5 . .
C52 C51 H51C 109.5 . .
H51A C51 H51C 109.5 . .
H51B C51 H51C 109.5 . .
C53 C52 C51 130.1(15) . .
C53 C52 H52A 104.8 . .
C51 C52 H52A 104.8 . .
C53 C52 H52B 104.8 . .
C51 C52 H52B 104.8 . .
H52A C52 H52B 105.8 . .
C52 C53 C54 128.2(16) . .
C52 C53 H53A 105.3 . .
C54 C53 H53A 105.3 . .
C52 C53 H53B 105.3 . .
C54 C53 H53B 105.3 . .
H53A C53 H53B 106.0 . .
C55 C54 C53 115.4(16) . .
C55 C54 H54A 108.4 . .
C53 C54 H54A 108.4 . .
C55 C54 H54B 108.4 . .
C53 C54 H54B 108.4 . .
H54A C54 H54B 107.5 . .
C56 C55 C54 121.6(19) . .
C56 C55 H55A 106.9 . .
C54 C55 H55A 106.9 . .
C56 C55 H55B 106.9 . .
C54 C55 H55B 106.9 . .
H55A C55 H55B 106.7 . .
C55 C56 H56A 109.5 . .
C55 C56 H56B 109.5 . .
H56A C56 H56B 109.5 . .
C55 C56 H56C 109.5 . .
H56A C56 H56C 109.5 . .
H56B C56 H56C 109.5 . .
C58 C57 H57A 109.5 . .
C58 C57 H57B 109.5 . .
H57A C57 H57B 109.5 . .
C58 C57 H57C 109.5 . .
H57A C57 H57C 109.5 . .
H57B C57 H57C 109.5 . .
C59 C58 C57 112(4) . .
C59 C58 H58A 109.2 . .
C57 C58 H58A 109.2 . .
C59 C58 H58B 109.2 . .
C57 C58 H58B 109.2 . .
H58A C58 H58B 107.9 . .
C58 C59 C59 124(6) . 2_655
C58 C59 H59A 106.3 . .
C59 C59 H59A 106.3 2_655 .
C58 C59 H59B 106.3 . .
C59 C59 H59B 106.3 2_655 .
H59A C59 H59B 106.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C22 1.337(6) .
F2 C23 1.339(6) .
F3 C24 1.368(6) .
F4 C25 1.357(6) .
F5 C26 1.348(6) .
F6 C28 1.373(7) .
F7 C29 1.342(9) .
F8 C30 1.350(7) .
F9 C31 1.376(8) .
F10 C32 1.328(7) .
F11 C34 1.351(6) .
F12 C35 1.351(5) .
F13 C36 1.355(5) .
F14 C37 1.348(6) .
F15 C38 1.346(5) .
N1 C1 1.395(5) .
N1 C4 1.397(5) .
N1 H1 0.8600 .
N2 C9 1.355(5) .
N2 C6 1.408(5) .
N3 C11 1.390(5) .
N3 C14 1.402(5) .
N3 H3 0.8600 .
N4 C19 1.369(5) .
N4 C16 1.385(5) .
N4 H4 0.8600 .
C1 C2 1.392(6) .
C1 C20 1.507(6) .
C2 C3 1.409(7) .
C2 H2 0.9300 .
C3 C4 1.409(6) .
C3 H3A 0.9300 .
C4 C5 1.423(6) .
C5 C6 1.395(6) .
C5 C21 1.530(6) .
C6 C7 1.477(6) .
C7 C8 1.352(6) .
C7 H7 0.9300 .
C8 C9 1.467(6) .
C8 H8 0.9300 .
C9 C10 1.437(6) .
C10 C11 1.386(6) .
C10 C27 1.502(6) .
C11 C12 1.468(6) .
C12 C13 1.354(6) .
C12 H12 0.9300 .
C13 C14 1.456(6) .
C13 H13 0.9300 .
C14 C15 1.375(6) .
C15 C17 1.488(6) .
C15 C33 1.488(6) .
C16 C17 1.367(6) .
C16 H16 0.9300 .
C17 C18 1.435(6) .
C18 C19 1.381(6) .
C18 H18 0.9300 .
C19 C20 1.550(6) .
C20 C45 1.548(6) .
C20 C39 1.577(6) .
C21 C26 1.370(6) .
C21 C22 1.375(7) .
C22 C23 1.415(7) .
C23 C24 1.350(8) .
C24 C25 1.356(8) .
C25 C26 1.396(7) .
C27 C28 1.349(8) .
C27 C32 1.422(8) .
C28 C29 1.413(9) .
C29 C30 1.388(11) .
C30 C31 1.319(10) .
C31 C32 1.393(8) .
C33 C38 1.398(7) .
C33 C34 1.399(6) .
C34 C35 1.386(6) .
C35 C36 1.372(7) .
C36 C37 1.386(7) .
C37 C38 1.399(7) .
C39 C44 1.371(6) .
C39 C40 1.418(6) .
C40 C41 1.388(7) .
C40 H40 0.9300 .
C41 C42 1.386(8) .
C41 H41 0.9300 .
C42 C43 1.361(8) .
C42 H42 0.9300 .
C43 C44 1.418(7) .
C43 H43 0.9300 .
C44 H44 0.9300 .
C45 C46 1.367(7) .
C45 C50 1.404(7) .
C46 C47 1.416(9) .
C46 H46 0.9300 .
C47 C48 1.356(11) .
C47 H47 0.9300 .
C48 C49 1.373(10) .
C48 H48 0.9300 .
C49 C50 1.390(8) .
C49 H49 0.9300 .
C50 H50 0.9300 .
C51 C52 1.496(18) .
C51 H51A 0.9600 .
C51 H51B 0.9600 .
C51 H51C 0.9600 .
C52 C53 1.321(17) .
C52 H52A 0.9700 .
C52 H52B 0.9700 .
C53 C54 1.505(18) .
C53 H53A 0.9700 .
C53 H53B 0.9700 .
C54 C55 1.460(19) .
C54 H54A 0.9700 .
C54 H54B 0.9700 .
C55 C56 1.43(2) .
C55 H55A 0.9700 .
C55 H55B 0.9700 .
C56 H56A 0.9600 .
C56 H56B 0.9600 .
C56 H56C 0.9600 .
C57 C58 1.54(4) .
C57 H57A 0.9600 .
C57 H57B 0.9600 .
C57 H57C 0.9600 .
C58 C59 1.47(4) .
C58 H58A 0.9700 .
C58 H58B 0.9700 .
C59 C59 1.51(6) 2_655
C59 H59A 0.9700 .
C59 H59B 0.9700 .
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_4
C4 N1 C1 C2 1.0(5) .
C4 N1 C1 C20 -172.7(4) .
N1 C1 C2 C3 -0.6(5) .
C20 C1 C2 C3 172.2(4) .
C1 C2 C3 C4 0.0(6) .
C1 N1 C4 C3 -1.0(5) .
C1 N1 C4 C5 178.8(4) .
C2 C3 C4 N1 0.6(5) .
C2 C3 C4 C5 -179.2(4) .
N1 C4 C5 C6 1.8(7) .
C3 C4 C5 C6 -178.4(5) .
N1 C4 C5 C21 -174.6(4) .
C3 C4 C5 C21 5.2(7) .
C4 C5 C6 N2 2.0(7) .
C21 C5 C6 N2 178.2(4) .
C4 C5 C6 C7 -172.0(4) .
C21 C5 C6 C7 4.3(6) .
C9 N2 C6 C5 -172.9(4) .
C9 N2 C6 C7 1.7(5) .
C5 C6 C7 C8 172.3(4) .
N2 C6 C7 C8 -2.4(5) .
C6 C7 C8 C9 2.1(5) .
C6 N2 C9 C10 -179.9(4) .
C6 N2 C9 C8 -0.4(5) .
C7 C8 C9 N2 -1.2(6) .
C7 C8 C9 C10 178.3(4) .
N2 C9 C10 C11 10.6(7) .
C8 C9 C10 C11 -168.8(5) .
N2 C9 C10 C27 -171.9(4) .
C8 C9 C10 C27 8.7(7) .
C9 C10 C11 N3 -0.5(7) .
C27 C10 C11 N3 -178.0(4) .
C9 C10 C11 C12 174.6(5) .
C27 C10 C11 C12 -3.0(7) .
C14 N3 C11 C10 174.5(4) .
C14 N3 C11 C12 -1.6(5) .
C10 C11 C12 C13 -173.9(5) .
N3 C11 C12 C13 1.9(5) .
C11 C12 C13 C14 -1.6(6) .
C11 N3 C14 C15 179.4(4) .
C11 N3 C14 C13 0.7(5) .
C12 C13 C14 C15 -178.1(5) .
C12 C13 C14 N3 0.6(5) .
N3 C14 C15 C17 -8.4(7) .
C13 C14 C15 C17 170.1(4) .
N3 C14 C15 C33 174.7(4) .
C13 C14 C15 C33 -6.9(8) .
C19 N4 C16 C17 -1.5(5) .
N4 C16 C17 C18 0.2(5) .
N4 C16 C17 C15 177.8(4) .
C14 C15 C17 C16 143.7(5) .
C33 C15 C17 C16 -39.2(7) .
C14 C15 C17 C18 -39.1(7) .
C33 C15 C17 C18 138.0(5) .
C16 C17 C18 C19 1.2(5) .
C15 C17 C18 C19 -176.5(4) .
C16 N4 C19 C18 2.3(5) .
C16 N4 C19 C20 179.5(4) .
C17 C18 C19 N4 -2.1(5) .
C17 C18 C19 C20 -179.3(4) .
C2 C1 C20 C45 -96.4(5) .
N1 C1 C20 C45 75.5(5) .
C2 C1 C20 C19 144.9(5) .
N1 C1 C20 C19 -43.2(5) .
C2 C1 C20 C39 25.2(6) .
N1 C1 C20 C39 -162.9(4) .
N4 C19 C20 C1 -99.5(5) .
C18 C19 C20 C1 77.2(5) .
N4 C19 C20 C45 140.4(4) .
C18 C19 C20 C45 -42.8(6) .
N4 C19 C20 C39 20.2(6) .
C18 C19 C20 C39 -163.0(4) .
C6 C5 C21 C26 95.8(5) .
C4 C5 C21 C26 -87.4(5) .
C6 C5 C21 C22 -86.9(5) .
C4 C5 C21 C22 89.9(5) .
C26 C21 C22 F1 179.4(5) .
C5 C21 C22 F1 1.9(7) .
C26 C21 C22 C23 -0.2(7) .
C5 C21 C22 C23 -177.6(5) .
F1 C22 C23 F2 -0.6(8) .
C21 C22 C23 F2 179.0(5) .
F1 C22 C23 C24 -179.0(5) .
C21 C22 C23 C24 0.6(8) .
F2 C23 C24 C25 -179.8(6) .
C22 C23 C24 C25 -1.4(8) .
F2 C23 C24 F3 1.3(8) .
C22 C23 C24 F3 179.7(5) .
C23 C24 C25 F4 179.5(5) .
F3 C24 C25 F4 -1.7(8) .
C23 C24 C25 C26 1.8(8) .
F3 C24 C25 C26 -179.4(4) .
C22 C21 C26 F5 -179.0(4) .
C5 C21 C26 F5 -1.5(7) .
C22 C21 C26 C25 0.5(7) .
C5 C21 C26 C25 178.0(4) .
C24 C25 C26 F5 178.1(5) .
F4 C25 C26 F5 0.4(7) .
C24 C25 C26 C21 -1.4(8) .
F4 C25 C26 C21 -179.1(4) .
C11 C10 C27 C28 -110.2(5) .
C9 C10 C27 C28 72.1(6) .
C11 C10 C27 C32 74.8(6) .
C9 C10 C27 C32 -102.9(5) .
C32 C27 C28 F6 179.4(4) .
C10 C27 C28 F6 4.1(7) .
C32 C27 C28 C29 -0.5(8) .
C10 C27 C28 C29 -175.8(5) .
C27 C28 C29 F7 -178.8(5) .
F6 C28 C29 F7 1.2(8) .
C27 C28 C29 C30 -0.7(9) .
F6 C28 C29 C30 179.3(5) .
F7 C29 C30 C31 179.8(6) .
C28 C29 C30 C31 1.7(10) .
F7 C29 C30 F8 -1.8(9) .
C28 C29 C30 F8 -179.9(5) .
F8 C30 C31 F9 -1.4(9) .
C29 C30 C31 F9 176.9(6) .
F8 C30 C31 C32 -179.7(5) .
C29 C30 C31 C32 -1.4(10) .
C30 C31 C32 F10 -179.4(6) .
F9 C31 C32 F10 2.2(7) .
C30 C31 C32 C27 0.1(8) .
F9 C31 C32 C27 -178.3(5) .
C28 C27 C32 F10 -179.7(4) .
C10 C27 C32 F10 -4.3(7) .
C28 C27 C32 C31 0.9(7) .
C10 C27 C32 C31 176.3(4) .
C14 C15 C33 C38 125.8(5) .
C17 C15 C33 C38 -51.3(6) .
C14 C15 C33 C34 -53.2(7) .
C17 C15 C33 C34 129.7(4) .
C38 C33 C34 F11 179.0(4) .
C15 C33 C34 F11 -2.0(6) .
C38 C33 C34 C35 -0.2(7) .
C15 C33 C34 C35 178.8(4) .
F11 C34 C35 F12 0.8(7) .
C33 C34 C35 F12 -180.0(4) .
F11 C34 C35 C36 -178.6(4) .
C33 C34 C35 C36 0.7(7) .
F12 C35 C36 F13 1.2(8) .
C34 C35 C36 F13 -179.4(4) .
F12 C35 C36 C37 179.3(5) .
C34 C35 C36 C37 -1.3(8) .
F13 C36 C37 F14 -0.1(8) .
C35 C36 C37 F14 -178.3(5) .
F13 C36 C37 C38 179.7(5) .
C35 C36 C37 C38 1.5(8) .
C34 C33 C38 F15 177.2(4) .
C15 C33 C38 F15 -1.9(7) .
C34 C33 C38 C37 0.4(7) .
C15 C33 C38 C37 -178.6(5) .
F14 C37 C38 F15 1.8(8) .
C36 C37 C38 F15 -178.0(5) .
F14 C37 C38 C33 178.7(5) .
C36 C37 C38 C33 -1.1(8) .
C1 C20 C39 C44 -128.5(5) .
C45 C20 C39 C44 -6.5(6) .
C19 C20 C39 C44 112.8(5) .
C1 C20 C39 C40 49.1(5) .
C45 C20 C39 C40 171.0(4) .
C19 C20 C39 C40 -69.7(5) .
C44 C39 C40 C41 -0.5(7) .
C20 C39 C40 C41 -178.2(4) .
C39 C40 C41 C42 -1.3(8) .
C40 C41 C42 C43 1.9(8) .
C41 C42 C43 C44 -0.6(8) .
C40 C39 C44 C43 1.8(7) .
C20 C39 C44 C43 179.3(4) .
C42 C43 C44 C39 -1.2(8) .
C1 C20 C45 C46 23.5(6) .
C19 C20 C45 C46 142.0(5) .
C39 C20 C45 C46 -98.0(5) .
C1 C20 C45 C50 -159.3(4) .
C19 C20 C45 C50 -40.8(5) .
C39 C20 C45 C50 79.2(5) .
C50 C45 C46 C47 1.0(9) .
C20 C45 C46 C47 178.3(6) .
C45 C46 C47 C48 -0.2(11) .
C46 C47 C48 C49 -1.1(13) .
C47 C48 C49 C50 1.4(12) .
C48 C49 C50 C45 -0.5(9) .
C46 C45 C50 C49 -0.7(8) .
C20 C45 C50 C49 -178.0(5) .
C51 C52 C53 C54 177.9(16) .
C52 C53 C54 C55 169.4(19) .
C53 C54 C55 C56 172.8(19) .
C57 C58 C59 C59 176(3) 2_655
