#------------------------------------------------------------------------------
#$Date: 2017-02-04 04:26:12 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191389 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/51/1545139.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_1545139
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            'C52 H24.5 Cl0.5 F15 N4 O'
_chemical_formula_weight         1023.98
_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                111.361(3)
_cell_angle_beta                 106.737(2)
_cell_angle_gamma                99.7020(10)
_cell_formula_units_Z            2
_cell_length_a                   12.5205(12)
_cell_length_b                   14.7808(13)
_cell_length_c                   15.1296(14)
_cell_measurement_temperature    298(2)
_cell_volume                     2376.9(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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0667
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11436
_diffrn_reflns_theta_full        24.52
_diffrn_reflns_theta_max         24.52
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.9465
_exptl_absorpt_correction_T_min  0.9337
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_refine_diff_density_max         1.112
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     719
_refine_ls_number_reflns         7766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1591
_refine_ls_R_factor_gt           0.0925
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2659
_refine_ls_wR_factor_ref         0.3166
_reflns_number_gt                4054
_reflns_number_total             7766
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03816_si_004.cif
_cod_data_source_block           160424f
_cod_depositor_comments
'Adding full bibliography for 1545137--1545139.cif.'
_cod_original_formula_sum        'C52 H24.50 Cl0.50 F15 N4 O'
_cod_database_code               1545139
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7848(4) 0.7781(4) 1.1931(3) 0.1060(14) Uani 1 1 d . . .
F2 F 0.9514(6) 0.9254(5) 1.3726(4) 0.169(3) Uani 1 1 d . . .
F3 F 1.1480(5) 1.0311(4) 1.3735(4) 0.176(3) Uani 1 1 d . . .
F4 F 1.1867(5) 0.9856(5) 1.1969(6) 0.177(3) Uani 1 1 d . . .
F5 F 1.0198(4) 0.8372(4) 1.0163(4) 0.1219(17) Uani 1 1 d . . .
F6 F 0.5761(3) 0.8660(3) 0.6562(3) 0.0808(11) Uani 1 1 d . . .
F7 F 0.4927(4) 0.9990(3) 0.5956(3) 0.0951(13) Uani 1 1 d . . .
F8 F 0.3216(4) 1.0641(3) 0.6509(3) 0.0887(12) Uani 1 1 d . . .
F9 F 0.2398(3) 1.0000(3) 0.7705(3) 0.0822(11) Uani 1 1 d . . .
F10 F 0.3194(3) 0.8635(3) 0.8296(3) 0.0712(10) Uani 1 1 d . . .
F11 F 0.1113(4) 0.3321(5) 0.5406(3) 0.153(3) Uani 1 1 d . . .
F12 F -0.0769(4) 0.2078(6) 0.3696(4) 0.177(3) Uani 1 1 d . . .
F13 F -0.0581(3) 0.1360(4) 0.1857(3) 0.1114(16) Uani 1 1 d . . .
F14 F 0.1504(4) 0.1934(5) 0.1739(3) 0.136(2) Uani 1 1 d . . .
F15 F 0.3406(3) 0.3223(4) 0.3452(3) 0.1131(17) Uani 1 1 d . . .
N4 N 0.8456(4) 0.4832(3) 0.9254(3) 0.0547(12) Uani 1 1 d . . .
H1 H 0.8823 0.4397 0.9288 0.066 Uiso 1 1 calc R . .
N3 N 0.6220(3) 0.7235(3) 0.8698(3) 0.0427(10) Uani 1 1 d . . .
N2 N 0.4343(3) 0.5839(3) 0.6701(3) 0.0409(10) Uani 1 1 d . . .
H3 H 0.4872 0.5760 0.7150 0.049 Uiso 1 1 calc R . .
N1 N 0.5159(3) 0.4071(3) 0.6727(3) 0.0425(10) Uani 1 1 d . . .
O1 O 0.9823(3) 0.6278(3) 1.0645(3) 0.0697(12) Uani 1 1 d . . .
C1 C 0.7357(4) 0.4603(4) 0.8490(4) 0.0420(12) Uani 1 1 d . . .
C4 C 0.7046(4) 0.5455(4) 0.8669(4) 0.0496(13) Uani 1 1 d . . .
H4 H 0.6353 0.5496 0.8269 0.059 Uiso 1 1 calc R . .
C3 C 0.7944(4) 0.6305(4) 0.9577(4) 0.0461(13) Uani 1 1 d . . .
C2 C 0.8861(4) 0.5851(4) 0.9940(4) 0.0514(14) Uani 1 1 d . . .
C5 C 0.7987(4) 0.7293(4) 1.0018(4) 0.0463(13) Uani 1 1 d . . .
C6 C 0.7167(4) 0.7746(4) 0.9574(4) 0.0439(12) Uani 1 1 d . . .
C7 C 0.7333(5) 0.8831(4) 0.9978(4) 0.0528(14) Uani 1 1 d . . .
H7 H 0.7922 0.9341 1.0579 0.063 Uiso 1 1 calc R . .
C8 C 0.6446(4) 0.8958(4) 0.9298(4) 0.0497(13) Uani 1 1 d . . .
H8 H 0.6316 0.9572 0.9345 0.060 Uiso 1 1 calc R . .
C9 C 0.5759(4) 0.7958(4) 0.8498(4) 0.0403(12) Uani 1 1 d . . .
C10 C 0.4839(4) 0.7741(4) 0.7621(4) 0.0421(12) Uani 1 1 d . . .
C11 C 0.4178(4) 0.6759(4) 0.6779(4) 0.0471(13) Uani 1 1 d . . .
C12 C 0.3230(5) 0.6552(4) 0.5887(5) 0.0685(18) Uani 1 1 d . . .
H12 H 0.2928 0.7033 0.5732 0.082 Uiso 1 1 calc R . .
C13 C 0.2831(5) 0.5523(4) 0.5290(4) 0.0628(16) Uani 1 1 d . . .
H13 H 0.2206 0.5181 0.4658 0.075 Uiso 1 1 calc R . .
C14 C 0.3528(4) 0.5070(4) 0.5794(4) 0.0465(13) Uani 1 1 d . . .
C15 C 0.3379(4) 0.3999(4) 0.5432(4) 0.0413(12) Uani 1 1 d . . .
C16 C 0.4108(4) 0.3540(4) 0.5867(4) 0.0426(12) Uani 1 1 d . . .
C17 C 0.3906(5) 0.2440(4) 0.5481(4) 0.0532(14) Uani 1 1 d . . .
H17 H 0.3276 0.1925 0.4919 0.064 Uiso 1 1 calc R . .
C18 C 0.4823(5) 0.2334(4) 0.6112(4) 0.0565(15) Uani 1 1 d . . .
H18 H 0.4954 0.1722 0.6070 0.068 Uiso 1 1 calc R . .
C19 C 0.5587(4) 0.3362(4) 0.6883(4) 0.0442(12) Uani 1 1 d . . .
C20 C 0.6734(4) 0.3511(4) 0.7701(4) 0.0425(12) Uani 1 1 d . . .
C21 C 0.8965(5) 0.8049(4) 1.1017(5) 0.0573(15) Uani 1 1 d . . .
C22 C 0.8824(6) 0.8278(5) 1.1920(5) 0.075(2) Uani 1 1 d . . .
C23 C 0.9680(8) 0.9042(6) 1.2843(6) 0.097(3) Uani 1 1 d . . .
C24 C 1.0677(9) 0.9574(6) 1.2842(8) 0.105(3) Uani 1 1 d . . .
C25 C 1.0852(7) 0.9348(6) 1.1970(8) 0.105(3) Uani 1 1 d . . .
C26 C 1.0001(6) 0.8581(5) 1.1036(6) 0.082(2) Uani 1 1 d . . .
C27 C 0.4494(4) 0.8606(4) 0.7440(4) 0.0411(12) Uani 1 1 d . . .
C28 C 0.4935(5) 0.8982(4) 0.6867(4) 0.0507(14) Uani 1 1 d . . .
C29 C 0.4501(5) 0.9669(4) 0.6543(4) 0.0574(15) Uani 1 1 d . . .
C30 C 0.3650(5) 0.9995(4) 0.6821(4) 0.0538(14) Uani 1 1 d . . .
C31 C 0.3219(5) 0.9662(4) 0.7433(4) 0.0522(14) Uani 1 1 d . . .
C32 C 0.3651(5) 0.8966(4) 0.7731(4) 0.0466(13) Uani 1 1 d . . .
C33 C 0.2316(4) 0.3308(4) 0.4477(4) 0.0410(12) Uani 1 1 d . . .
C34 C 0.1250(5) 0.2977(5) 0.4495(4) 0.0703(18) Uani 1 1 d . . .
C35 C 0.0275(5) 0.2338(6) 0.3628(5) 0.081(2) Uani 1 1 d . . .
C36 C 0.0359(5) 0.2013(5) 0.2713(4) 0.0679(17) Uani 1 1 d . . .
C37 C 0.1405(5) 0.2300(5) 0.2647(4) 0.0696(18) Uani 1 1 d . . .
C38 C 0.2371(5) 0.2949(5) 0.3535(4) 0.0566(15) Uani 1 1 d . . .
C39 C 0.6448(5) 0.2900(4) 0.8303(4) 0.0506(13) Uani 1 1 d . . .
C40 C 0.5408(5) 0.2809(5) 0.8452(5) 0.0679(17) Uani 1 1 d . . .
H40 H 0.4861 0.3078 0.8164 0.081 Uiso 1 1 calc R . .
C41 C 0.5168(7) 0.2301(5) 0.9048(5) 0.082(2) Uani 1 1 d . . .
H41 H 0.4470 0.2249 0.9156 0.098 Uiso 1 1 calc R . .
C42 C 0.5959(7) 0.1894(6) 0.9458(5) 0.086(2) Uani 1 1 d . . .
H42 H 0.5796 0.1551 0.9833 0.104 Uiso 1 1 calc R . .
C43 C 0.6975(7) 0.1989(5) 0.9318(5) 0.082(2) Uani 1 1 d . . .
H43 H 0.7515 0.1716 0.9611 0.099 Uiso 1 1 calc R . .
C44 C 0.7248(5) 0.2486(4) 0.8747(4) 0.0606(16) Uani 1 1 d . . .
H44 H 0.7959 0.2541 0.8663 0.073 Uiso 1 1 calc R . .
C45 C 0.7484(5) 0.3092(4) 0.7096(4) 0.0495(13) Uani 1 1 d . . .
C46 C 0.7355(5) 0.2066(4) 0.6628(4) 0.0596(15) Uani 1 1 d . . .
H46 H 0.6857 0.1607 0.6732 0.072 Uiso 1 1 calc R . .
C47 C 0.7963(6) 0.1706(6) 0.5997(5) 0.077(2) Uani 1 1 d . . .
H47 H 0.7850 0.1009 0.5670 0.093 Uiso 1 1 calc R . .
C48 C 0.8723(7) 0.2372(7) 0.5860(5) 0.080(2) Uani 1 1 d . . .
H48 H 0.9133 0.2128 0.5448 0.096 Uiso 1 1 calc R . .
C49 C 0.8884(6) 0.3399(6) 0.6325(6) 0.080(2) Uani 1 1 d . . .
H49 H 0.9409 0.3849 0.6234 0.096 Uiso 1 1 calc R . .
C50 C 0.8256(5) 0.3774(5) 0.6939(5) 0.0609(15) Uani 1 1 d . . .
H50 H 0.8351 0.4469 0.7241 0.073 Uiso 1 1 calc R . .
C51 C 0.102(4) 0.592(3) 0.679(3) 0.119(13) Uani 0.25 1 d P A 1
H51A H 0.1488 0.6513 0.6807 0.179 Uiso 0.25 1 calc PR A 1
H51B H 0.0240 0.5710 0.6290 0.179 Uiso 0.25 1 calc PR A 1
H51C H 0.1359 0.5375 0.6606 0.179 Uiso 0.25 1 calc PR A 1
C52 C 0.097(4) 0.616(2) 0.784(3) 0.103(12) Uani 0.25 1 d P A 1
H52A H 0.0171 0.5871 0.7756 0.123 Uiso 0.25 1 calc PR A 1
H52B H 0.1185 0.6894 0.8227 0.123 Uiso 0.25 1 calc PR A 1
C53 C 0.177(9) 0.576(9) 0.847(10) 0.15(3) Uani 0.25 1 d P A 1
H53A H 0.1331 0.5422 0.8756 0.174 Uiso 0.25 1 calc PR A 1
H53B H 0.2407 0.6333 0.9039 0.174 Uiso 0.25 1 calc PR A 1
C54 C 0.231(4) 0.501(4) 0.788(3) 0.129(15) Uani 0.25 1 d P A 1
H54A H 0.1680 0.4451 0.7282 0.155 Uiso 0.25 1 calc PR A 1
H54B H 0.2804 0.5353 0.7639 0.155 Uiso 0.25 1 calc PR A 1
C55 C 0.302(4) 0.457(3) 0.850(4) 0.137(15) Uani 0.25 1 d P A 1
H55A H 0.2679 0.4525 0.8995 0.165 Uiso 0.25 1 calc PR A 1
H55B H 0.2937 0.3878 0.8048 0.165 Uiso 0.25 1 calc PR A 1
C56 C 0.429(3) 0.514(3) 0.908(3) 0.118(13) Uani 0.25 1 d P A 1
H56A H 0.4370 0.5861 0.9311 0.141 Uiso 0.25 1 calc PR A 1
H56B H 0.4668 0.4969 0.8586 0.141 Uiso 0.25 1 calc PR A 1
C57 C 0.5000 0.5000 1.0000 0.104(7) Uani 0.50 2 d SP . 1
H57A H 0.5820 0.5236 1.0140 0.155 Uiso 0.25 1 d PR . 1
H57B H 0.4840 0.5405 1.0577 0.155 Uiso 0.25 1 d PR . 1
H57C H 0.4785 0.4298 0.9880 0.155 Uiso 0.25 1 d PR . 1
Cl1 Cl 0.0331(13) 0.6386(9) 0.8463(11) 0.162(5) Uani 0.25 1 d P B 2
C58 C 0.124(8) 0.563(9) 0.840(10) 0.14(3) Uani 0.25 1 d P B 2
H58A H 0.0787 0.4920 0.8114 0.162 Uiso 0.25 1 calc PR B 2
H58B H 0.1808 0.5827 0.9081 0.162 Uiso 0.25 1 calc PR B 2
Cl2 Cl 0.1910(16) 0.5837(12) 0.7624(13) 0.166(6) Uani 0.25 1 d P B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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
C2 N4 C1 110.7(4) . .
C2 N4 H1 124.6 . .
C1 N4 H1 124.6 . .
C6 N3 C9 106.5(4) . .
C14 N2 C11 109.2(4) . .
C14 N2 H3 125.4 . .
C11 N2 H3 125.4 . .
C19 N1 C16 105.4(4) . .
C4 C1 N4 108.8(4) . .
C4 C1 C20 132.3(4) . .
N4 C1 C20 118.7(4) . .
C1 C4 C3 110.2(4) . .
C1 C4 H4 124.9 . .
C3 C4 H4 124.9 . .
C5 C3 C4 129.6(4) . .
C5 C3 C2 126.0(5) . .
C4 C3 C2 104.3(4) . .
O1 C2 N4 125.0(5) . .
O1 C2 C3 128.9(5) . .
N4 C2 C3 105.9(4) . .
C3 C5 C6 124.9(5) . .
C3 C5 C21 121.4(4) . .
C6 C5 C21 113.7(4) . .
N3 C6 C7 110.9(4) . .
N3 C6 C5 125.1(4) . .
C7 C6 C5 123.7(4) . .
C8 C7 C6 106.1(4) . .
C8 C7 H7 127.0 . .
C6 C7 H7 127.0 . .
C7 C8 C9 106.6(4) . .
C7 C8 H8 126.7 . .
C9 C8 H8 126.7 . .
C10 C9 N3 124.0(4) . .
C10 C9 C8 125.9(4) . .
N3 C9 C8 109.9(4) . .
C9 C10 C11 127.4(4) . .
C9 C10 C27 119.1(4) . .
C11 C10 C27 113.3(4) . .
N2 C11 C12 107.2(5) . .
N2 C11 C10 126.3(4) . .
C12 C11 C10 126.5(5) . .
C13 C12 C11 108.1(5) . .
C13 C12 H12 126.0 . .
C11 C12 H12 126.0 . .
C12 C13 C14 108.2(5) . .
C12 C13 H13 125.9 . .
C14 C13 H13 125.9 . .
N2 C14 C13 107.3(4) . .
N2 C14 C15 126.9(4) . .
C13 C14 C15 125.7(5) . .
C16 C15 C14 126.9(4) . .
C16 C15 C33 117.1(4) . .
C14 C15 C33 116.0(4) . .
C15 C16 N1 124.5(4) . .
C15 C16 C17 124.9(4) . .
N1 C16 C17 110.6(4) . .
C18 C17 C16 105.1(5) . .
C18 C17 H17 127.5 . .
C16 C17 H17 127.5 . .
C17 C18 C19 107.6(5) . .
C17 C18 H18 126.2 . .
C19 C18 H18 126.2 . .
N1 C19 C18 111.3(4) . .
N1 C19 C20 127.8(4) . .
C18 C19 C20 120.8(4) . .
C1 C20 C19 114.1(4) . .
C1 C20 C45 111.2(4) . .
C19 C20 C45 104.6(4) . .
C1 C20 C39 106.2(4) . .
C19 C20 C39 107.9(4) . .
C45 C20 C39 113.0(4) . .
C22 C21 C26 117.9(6) . .
C22 C21 C5 120.7(6) . .
C26 C21 C5 121.2(6) . .
F1 C22 C21 119.5(6) . .
F1 C22 C23 119.0(8) . .
C21 C22 C23 121.5(8) . .
F2 C23 C24 120.1(8) . .
F2 C23 C22 120.1(10) . .
C24 C23 C22 119.8(9) . .
C25 C24 F3 121.2(11) . .
C25 C24 C23 120.1(8) . .
F3 C24 C23 118.7(11) . .
C24 C25 F4 120.4(9) . .
C24 C25 C26 120.9(9) . .
F4 C25 C26 118.8(10) . .
F5 C26 C21 120.5(6) . .
F5 C26 C25 119.6(8) . .
C21 C26 C25 119.9(9) . .
C32 C27 C28 117.7(4) . .
C32 C27 C10 122.3(4) . .
C28 C27 C10 119.6(4) . .
F6 C28 C27 120.4(4) . .
F6 C28 C29 118.0(5) . .
C27 C28 C29 121.6(5) . .
F7 C29 C30 120.7(5) . .
F7 C29 C28 119.7(5) . .
C30 C29 C28 119.6(5) . .
F8 C30 C29 120.4(5) . .
F8 C30 C31 119.3(5) . .
C29 C30 C31 120.3(5) . .
F9 C31 C30 119.3(5) . .
F9 C31 C32 121.6(5) . .
C30 C31 C32 119.1(5) . .
F10 C32 C27 120.6(4) . .
F10 C32 C31 117.7(5) . .
C27 C32 C31 121.7(5) . .
C34 C33 C38 115.3(5) . .
C34 C33 C15 122.8(5) . .
C38 C33 C15 121.8(4) . .
C33 C34 F11 119.0(5) . .
C33 C34 C35 123.4(5) . .
F11 C34 C35 117.6(5) . .
C36 C35 F12 120.0(6) . .
C36 C35 C34 119.6(6) . .
F12 C35 C34 120.3(6) . .
C35 C36 F13 120.4(6) . .
C35 C36 C37 119.7(6) . .
F13 C36 C37 119.8(6) . .
F14 C37 C36 119.8(6) . .
F14 C37 C38 120.9(6) . .
C36 C37 C38 119.2(5) . .
F15 C38 C33 119.0(5) . .
F15 C38 C37 118.3(5) . .
C33 C38 C37 122.7(5) . .
C40 C39 C44 118.3(5) . .
C40 C39 C20 119.8(5) . .
C44 C39 C20 121.8(5) . .
C39 C40 C41 120.2(6) . .
C39 C40 H40 119.9 . .
C41 C40 H40 119.9 . .
C42 C41 C40 120.0(7) . .
C42 C41 H41 120.0 . .
C40 C41 H41 120.0 . .
C43 C42 C41 119.8(6) . .
C43 C42 H42 120.1 . .
C41 C42 H42 120.1 . .
C42 C43 C44 121.9(6) . .
C42 C43 H43 119.0 . .
C44 C43 H43 119.0 . .
C39 C44 C43 119.7(6) . .
C39 C44 H44 120.1 . .
C43 C44 H44 120.1 . .
C46 C45 C50 118.5(5) . .
C46 C45 C20 122.5(5) . .
C50 C45 C20 118.7(5) . .
C45 C46 C47 120.8(6) . .
C45 C46 H46 119.6 . .
C47 C46 H46 119.6 . .
C48 C47 C46 120.4(6) . .
C48 C47 H47 119.8 . .
C46 C47 H47 119.8 . .
C47 C48 C49 120.3(7) . .
C47 C48 H48 119.8 . .
C49 C48 H48 119.8 . .
C48 C49 C50 120.2(7) . .
C48 C49 H49 119.9 . .
C50 C49 H49 119.9 . .
C49 C50 C45 119.8(6) . .
C49 C50 H50 120.1 . .
C45 C50 H50 120.1 . .
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 . .
C51 C52 C53 114(6) . .
C51 C52 H52A 108.7 . .
C53 C52 H52A 108.7 . .
C51 C52 H52B 108.7 . .
C53 C52 H52B 108.7 . .
H52A C52 H52B 107.6 . .
C52 C53 C54 116(9) . .
C52 C53 H53A 108.4 . .
C54 C53 H53A 108.4 . .
C52 C53 H53B 108.4 . .
C54 C53 H53B 108.4 . .
H53A C53 H53B 107.5 . .
C55 C54 C53 114(7) . .
C55 C54 H54A 108.8 . .
C53 C54 H54A 108.8 . .
C55 C54 H54B 108.8 . .
C53 C54 H54B 108.8 . .
H54A C54 H54B 107.7 . .
C56 C55 C54 116(4) . .
C56 C55 H55A 108.2 . .
C54 C55 H55A 108.2 . .
C56 C55 H55B 108.2 . .
C54 C55 H55B 108.2 . .
H55A C55 H55B 107.3 . .
C55 C56 C57 120(4) . .
C55 C56 H56A 107.2 . .
C57 C56 H56A 107.2 . .
C55 C56 H56B 107.2 . .
C57 C56 H56B 107.2 . .
H56A C56 H56B 106.9 . .
C56 C57 C56 180.00(2) . 2_667
C56 C57 H57A 109.5 . .
C56 C57 H57A 70.5 2_667 .
C56 C57 H57B 107.5 . .
C56 C57 H57B 72.5 2_667 .
H57A C57 H57B 109.5 . .
C56 C57 H57C 111.4 . .
C56 C57 H57C 68.6 2_667 .
H57A C57 H57C 109.5 . .
H57B C57 H57C 109.5 . .
Cl1 C58 Cl2 105(8) . .
Cl1 C58 H58A 110.7 . .
Cl2 C58 H58A 110.7 . .
Cl1 C58 H58B 110.7 . .
Cl2 C58 H58B 110.7 . .
H58A C58 H58B 108.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C22 1.323(9) .
F2 C23 1.342(10) .
F3 C24 1.341(9) .
F4 C25 1.364(11) .
F5 C26 1.347(9) .
F6 C28 1.338(6) .
F7 C29 1.339(6) .
F8 C30 1.335(6) .
F9 C31 1.320(6) .
F10 C32 1.337(6) .
F11 C34 1.357(7) .
F12 C35 1.343(7) .
F13 C36 1.350(6) .
F14 C37 1.332(7) .
F15 C38 1.346(6) .
N4 C2 1.379(7) .
N4 C1 1.409(6) .
N4 H1 0.8600 .
N3 C6 1.340(6) .
N3 C9 1.383(6) .
N2 C14 1.372(6) .
N2 C11 1.377(6) .
N2 H3 0.8600 .
N1 C19 1.317(6) .
N1 C16 1.401(6) .
O1 C2 1.225(6) .
C1 C4 1.337(7) .
C1 C20 1.509(7) .
C4 C3 1.452(7) .
C4 H4 0.9300 .
C3 C5 1.350(7) .
C3 C2 1.496(7) .
C5 C6 1.455(7) .
C5 C21 1.509(7) .
C6 C7 1.446(7) .
C7 C8 1.371(7) .
C7 H7 0.9300 .
C8 C9 1.434(7) .
C8 H8 0.9300 .
C9 C10 1.370(6) .
C10 C11 1.433(7) .
C10 C27 1.507(6) .
C11 C12 1.407(7) .
C12 C13 1.365(8) .
C12 H12 0.9300 .
C13 C14 1.406(7) .
C13 H13 0.9300 .
C14 C15 1.432(7) .
C15 C16 1.384(6) .
C15 C33 1.504(7) .
C16 C17 1.460(7) .
C17 C18 1.339(7) .
C17 H17 0.9300 .
C18 C19 1.470(7) .
C18 H18 0.9300 .
C19 C20 1.521(7) .
C20 C45 1.542(8) .
C20 C39 1.567(7) .
C21 C22 1.355(9) .
C21 C26 1.386(10) .
C22 C23 1.398(10) .
C23 C24 1.359(13) .
C24 C25 1.331(13) .
C25 C26 1.406(10) .
C27 C32 1.369(7) .
C27 C28 1.374(7) .
C28 C29 1.402(7) .
C29 C30 1.352(8) .
C30 C31 1.386(8) .
C31 C32 1.394(7) .
C33 C34 1.354(7) .
C33 C38 1.354(7) .
C34 C35 1.375(8) .
C35 C36 1.333(8) .
C36 C37 1.350(8) .
C37 C38 1.387(8) .
C39 C40 1.377(8) .
C39 C44 1.395(7) .
C40 C41 1.428(9) .
C40 H40 0.9300 .
C41 C42 1.358(10) .
C41 H41 0.9300 .
C42 C43 1.342(10) .
C42 H42 0.9300 .
C43 C44 1.397(9) .
C43 H43 0.9300 .
C44 H44 0.9300 .
C45 C46 1.377(8) .
C45 C50 1.408(8) .
C46 C47 1.400(9) .
C46 H46 0.9300 .
C47 C48 1.366(10) .
C47 H47 0.9300 .
C48 C49 1.369(10) .
C48 H48 0.9300 .
C49 C50 1.408(9) .
C49 H49 0.9300 .
C50 H50 0.9300 .
C51 C52 1.52(6) .
C51 H51A 0.9600 .
C51 H51B 0.9600 .
C51 H51C 0.9600 .
C52 C53 1.53(17) .
C52 H52A 0.9700 .
C52 H52B 0.9700 .
C53 C54 1.53(14) .
C53 H53A 0.9700 .
C53 H53B 0.9700 .
C54 C55 1.50(6) .
C54 H54A 0.9700 .
C54 H54B 0.9700 .
C55 C56 1.49(5) .
C55 H55A 0.9700 .
C55 H55B 0.9700 .
C56 C57 1.53(5) .
C56 H56A 0.9700 .
C56 H56B 0.9700 .
C57 C56 1.53(5) 2_667
C57 H57A 0.9600 .
C57 H57B 0.9600 .
C57 H57C 0.9601 .
Cl1 C58 1.71(15) .
C58 Cl2 1.71(12) .
C58 H58A 0.9700 .
C58 H58B 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
C2 N4 C1 C4 0.0(6) .
C2 N4 C1 C20 -176.5(5) .
N4 C1 C4 C3 0.2(6) .
C20 C1 C4 C3 176.0(5) .
C1 C4 C3 C5 179.2(6) .
C1 C4 C3 C2 -0.3(6) .
C1 N4 C2 O1 -175.2(5) .
C1 N4 C2 C3 -0.2(6) .
C5 C3 C2 O1 -4.4(10) .
C4 C3 C2 O1 175.1(6) .
C5 C3 C2 N4 -179.2(5) .
C4 C3 C2 N4 0.3(6) .
C4 C3 C5 C6 -8.4(9) .
C2 C3 C5 C6 171.0(5) .
C4 C3 C5 C21 175.2(6) .
C2 C3 C5 C21 -5.5(9) .
C9 N3 C6 C7 1.0(6) .
C9 N3 C6 C5 -173.7(5) .
C3 C5 C6 N3 4.0(9) .
C21 C5 C6 N3 -179.3(5) .
C3 C5 C6 C7 -170.0(5) .
C21 C5 C6 C7 6.7(8) .
N3 C6 C7 C8 -0.7(6) .
C5 C6 C7 C8 174.1(5) .
C6 C7 C8 C9 0.1(6) .
C6 N3 C9 C10 174.3(5) .
C6 N3 C9 C8 -1.0(6) .
C7 C8 C9 C10 -174.6(5) .
C7 C8 C9 N3 0.5(6) .
N3 C9 C10 C11 1.5(8) .
C8 C9 C10 C11 176.0(5) .
N3 C9 C10 C27 -173.8(4) .
C8 C9 C10 C27 0.7(8) .
C14 N2 C11 C12 -0.1(6) .
C14 N2 C11 C10 178.9(5) .
C9 C10 C11 N2 0.6(9) .
C27 C10 C11 N2 176.2(5) .
C9 C10 C11 C12 179.5(6) .
C27 C10 C11 C12 -4.9(8) .
N2 C11 C12 C13 0.4(7) .
C10 C11 C12 C13 -178.7(5) .
C11 C12 C13 C14 -0.5(7) .
C11 N2 C14 C13 -0.1(6) .
C11 N2 C14 C15 -178.2(5) .
C12 C13 C14 N2 0.4(7) .
C12 C13 C14 C15 178.5(5) .
N2 C14 C15 C16 -8.0(9) .
C13 C14 C15 C16 174.2(5) .
N2 C14 C15 C33 172.0(5) .
C13 C14 C15 C33 -5.7(8) .
C14 C15 C16 N1 -3.0(8) .
C33 C15 C16 N1 176.9(4) .
C14 C15 C16 C17 178.6(5) .
C33 C15 C16 C17 -1.4(7) .
C19 N1 C16 C15 -179.1(5) .
C19 N1 C16 C17 -0.6(6) .
C15 C16 C17 C18 178.9(5) .
N1 C16 C17 C18 0.4(6) .
C16 C17 C18 C19 0.0(6) .
C16 N1 C19 C18 0.6(6) .
C16 N1 C19 C20 178.1(5) .
C17 C18 C19 N1 -0.4(7) .
C17 C18 C19 C20 -178.1(5) .
C4 C1 C20 C19 7.4(8) .
N4 C1 C20 C19 -177.1(4) .
C4 C1 C20 C45 125.5(6) .
N4 C1 C20 C45 -59.0(6) .
C4 C1 C20 C39 -111.2(6) .
N4 C1 C20 C39 64.3(6) .
N1 C19 C20 C1 8.1(7) .
C18 C19 C20 C1 -174.6(5) .
N1 C19 C20 C45 -113.7(6) .
C18 C19 C20 C45 63.6(6) .
N1 C19 C20 C39 125.8(5) .
C18 C19 C20 C39 -56.9(6) .
C3 C5 C21 C22 -96.6(7) .
C6 C5 C21 C22 86.5(6) .
C3 C5 C21 C26 88.0(7) .
C6 C5 C21 C26 -88.9(6) .
C26 C21 C22 F1 -179.7(5) .
C5 C21 C22 F1 4.7(8) .
C26 C21 C22 C23 1.4(9) .
C5 C21 C22 C23 -174.2(5) .
F1 C22 C23 F2 0.9(10) .
C21 C22 C23 F2 179.8(6) .
F1 C22 C23 C24 -178.7(6) .
C21 C22 C23 C24 0.2(10) .
F2 C23 C24 C25 178.5(7) .
C22 C23 C24 C25 -1.9(12) .
F2 C23 C24 F3 -0.3(11) .
C22 C23 C24 F3 179.3(6) .
F3 C24 C25 F4 0.9(12) .
C23 C24 C25 F4 -177.9(7) .
F3 C24 C25 C26 -179.4(6) .
C23 C24 C25 C26 1.8(12) .
C22 C21 C26 F5 178.8(6) .
C5 C21 C26 F5 -5.7(9) .
C22 C21 C26 C25 -1.4(9) .
C5 C21 C26 C25 174.1(6) .
C24 C25 C26 F5 179.6(7) .
F4 C25 C26 F5 -0.7(10) .
C24 C25 C26 C21 -0.1(11) .
F4 C25 C26 C21 179.5(6) .
C9 C10 C27 C32 -92.9(6) .
C11 C10 C27 C32 91.2(6) .
C9 C10 C27 C28 94.5(6) .
C11 C10 C27 C28 -81.5(6) .
C32 C27 C28 F6 179.9(5) .
C10 C27 C28 F6 -7.2(8) .
C32 C27 C28 C29 -3.2(8) .
C10 C27 C28 C29 169.7(5) .
F6 C28 C29 F7 -0.8(8) .
C27 C28 C29 F7 -177.8(5) .
F6 C28 C29 C30 178.8(5) .
C27 C28 C29 C30 1.8(9) .
F7 C29 C30 F8 0.3(9) .
C28 C29 C30 F8 -179.2(5) .
F7 C29 C30 C31 -179.7(5) .
C28 C29 C30 C31 0.8(9) .
F8 C30 C31 F9 -0.8(8) .
C29 C30 C31 F9 179.2(5) .
F8 C30 C31 C32 178.2(5) .
C29 C30 C31 C32 -1.8(8) .
C28 C27 C32 F10 -179.5(5) .
C10 C27 C32 F10 7.7(8) .
C28 C27 C32 C31 2.2(8) .
C10 C27 C32 C31 -170.6(5) .
F9 C31 C32 F10 0.9(8) .
C30 C31 C32 F10 -178.1(5) .
F9 C31 C32 C27 179.3(5) .
C30 C31 C32 C27 0.3(8) .
C16 C15 C33 C34 94.6(6) .
C14 C15 C33 C34 -85.5(7) .
C16 C15 C33 C38 -83.5(6) .
C14 C15 C33 C38 96.4(6) .
C38 C33 C34 F11 -178.4(6) .
C15 C33 C34 F11 3.5(9) .
C38 C33 C34 C35 -1.2(10) .
C15 C33 C34 C35 -179.4(6) .
C33 C34 C35 C36 0.2(12) .
F11 C34 C35 C36 177.4(7) .
C33 C34 C35 F12 -176.8(7) .
F11 C34 C35 F12 0.4(12) .
F12 C35 C36 F13 -5.1(12) .
C34 C35 C36 F13 177.9(7) .
F12 C35 C36 C37 178.1(7) .
C34 C35 C36 C37 1.2(12) .
C35 C36 C37 F14 176.5(7) .
F13 C36 C37 F14 -0.3(11) .
C35 C36 C37 C38 -1.4(11) .
F13 C36 C37 C38 -178.2(6) .
C34 C33 C38 F15 -178.5(5) .
C15 C33 C38 F15 -0.3(8) .
C34 C33 C38 C37 0.9(9) .
C15 C33 C38 C37 179.1(5) .
F14 C37 C38 F15 1.9(10) .
C36 C37 C38 F15 179.8(6) .
F14 C37 C38 C33 -177.5(6) .
C36 C37 C38 C33 0.4(10) .
C1 C20 C39 C40 89.4(6) .
C19 C20 C39 C40 -33.3(7) .
C45 C20 C39 C40 -148.4(5) .
C1 C20 C39 C44 -87.1(6) .
C19 C20 C39 C44 150.2(5) .
C45 C20 C39 C44 35.1(7) .
C44 C39 C40 C41 0.0(9) .
C20 C39 C40 C41 -176.6(5) .
C39 C40 C41 C42 -0.9(10) .
C40 C41 C42 C43 1.4(11) .
C41 C42 C43 C44 -0.9(12) .
C40 C39 C44 C43 0.5(9) .
C20 C39 C44 C43 177.0(5) .
C42 C43 C44 C39 0.0(10) .
C1 C20 C45 C46 155.2(5) .
C19 C20 C45 C46 -81.2(5) .
C39 C20 C45 C46 35.9(6) .
C1 C20 C45 C50 -30.7(6) .
C19 C20 C45 C50 93.0(5) .
C39 C20 C45 C50 -149.9(5) .
C50 C45 C46 C47 -0.9(8) .
C20 C45 C46 C47 173.3(5) .
C45 C46 C47 C48 1.9(9) .
C46 C47 C48 C49 -1.0(10) .
C47 C48 C49 C50 -0.8(10) .
C48 C49 C50 C45 1.7(9) .
C46 C45 C50 C49 -0.8(8) .
C20 C45 C50 C49 -175.2(5) .
C51 C52 C53 C54 -11(7) .
C52 C53 C54 C55 -176(5) .
C53 C54 C55 C56 -91(5) .
C54 C55 C56 C57 159(3) .
C55 C56 C57 C56 -165(47) 2_667
