#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:46:54 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180315 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/29/7152993.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_7152993
loop_
_publ_author_name
'Dudkin, Sergii'
'Iaroshenko, Viktor O.'
'Sosnovskikh, Vyacheslav Ya'
'Tolmachev, Andrey A.'
'Villinger, Alexander'
'Langer, Peter'
_publ_section_title
;
 Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5351
_journal_page_last               5361
_journal_paper_doi               10.1039/c3ob26837c
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C17 H12 F7 N3 O3, C H Cl3'
_chemical_formula_sum            'C18 H13 Cl3 F7 N3 O3'
_chemical_formula_weight         558.66
_chemical_name_systematic
;
?
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.776(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.2256(8)
_cell_length_b                   6.8967(4)
_cell_length_c                   12.7724(8)
_cell_measurement_reflns_used    4220
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      60.628
_cell_measurement_theta_min      5.907
_cell_volume                     1071.45(12)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10034
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_T_max  0.9599
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         2781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0478
_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)+(0.0821P)²+0.4737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1491
_reflns_number_gt                2118
_reflns_number_total             2781
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3ob26837c.txt
_cod_data_source_block           is_sd206
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7152993
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_group
O3 O 0.78279(17) 0.2060(4) 0.20869(17) 0.0319(10) Uani 0.50 1 d P .
N1 N 1.10447(15) 0.2500 0.30481(15) 0.0266(5) Uani 1 2 d S .
N2 N 1.07953(16) 0.2500 0.48001(15) 0.0255(4) Uani 1 2 d S .
N3 N 0.95685(17) 0.2500 0.17222(15) 0.0271(5) Uani 1 2 d S .
O1 O 1.13403(16) 0.2500 0.13250(15) 0.0454(6) Uani 1 2 d S .
O2 O 1.05263(15) 0.2500 0.84994(13) 0.0331(4) Uani 1 2 d S .
F1 F 0.6921(2) 0.4404(4) 0.49188(17) 0.0372(6) Uani 0.50 1 d P .
F2 F 0.7086(3) 0.4505(5) 0.3276(3) 0.0289(7) Uani 0.50 1 d P .
F3 F 0.6247(2) 0.1032(5) 0.4977(2) 0.0519(7) Uani 0.50 1 d P .
F4 F 0.6957(4) 0.0001(6) 0.3604(3) 0.0439(10) Uani 0.50 1 d P .
F5 F 0.4878(3) 0.3444(7) 0.3708(3) 0.0692(11) Uani 0.50 1 d P .
F6 F 0.4718(2) 0.0352(7) 0.3446(3) 0.0631(9) Uani 0.50 1 d P .
F7 F 0.54791(16) 0.2500 0.23472(16) 0.0769(8) Uani 1 2 d S .
C1 C 1.0696(2) 0.2500 0.19927(19) 0.0307(6) Uani 1 2 d S .
C2 C 1.03327(18) 0.2500 0.38325(18) 0.0242(5) Uani 1 2 d S .
C3 C 1.01426(18) 0.2500 0.55987(18) 0.0238(5) Uani 1 2 d S .
C4 C 1.06889(19) 0.2500 0.66269(18) 0.0245(5) Uani 1 2 d S .
H4 H 1.1469 0.2500 0.6729 0.029 Uiso 1 2 calc SR .
C5 C 1.0089(2) 0.2500 0.74782(18) 0.0265(5) Uani 1 2 d S .
C6 C 0.8927(2) 0.2500 0.73200(19) 0.0313(6) Uani 1 2 d S .
H6 H 0.8517 0.2500 0.7913 0.038 Uiso 1 2 calc SR .
C7 C 0.8386(2) 0.2500 0.6341(2) 0.0332(6) Uani 1 2 d S .
H7 H 0.7605 0.2500 0.6261 0.040 Uiso 1 2 calc SR .
C8 C 0.89688(19) 0.2500 0.54226(19) 0.0313(6) Uani 1 2 d S .
C9 C 0.8499(2) 0.2825(8) 0.4360(2) 0.0217(15) Uani 0.50 1 d P .
C10 C 0.91761(18) 0.2500 0.35447(18) 0.0242(5) Uani 1 2 d S .
C11 C 0.87735(19) 0.2500 0.24211(18) 0.0250(5) Uani 1 2 d S .
C12 C 0.9196(2) 0.2500 0.05898(19) 0.0346(6) Uani 1 2 d S .
H12A H 0.9707 0.3266 0.0213 0.052 Uiso 0.50 1 calc PR .
H12B H 0.8459 0.3069 0.0477 0.052 Uiso 0.50 1 calc PR .
H12C H 0.9175 0.1165 0.0326 0.052 Uiso 0.50 1 calc PR .
C13 C 1.22425(19) 0.2500 0.3327(2) 0.0362(7) Uani 1 2 d S .
H13A H 1.2410 0.3049 0.4033 0.054 Uiso 0.50 1 calc PR .
H13B H 1.2596 0.3284 0.2817 0.054 Uiso 0.50 1 calc PR .
H13C H 1.2519 0.1167 0.3317 0.054 Uiso 0.50 1 calc PR .
C14 C 1.1698(2) 0.2500 0.8708(2) 0.0350(6) Uani 1 2 d S .
H14A H 1.1992 0.1276 0.8465 0.052 Uiso 0.50 1 calc PR .
H14B H 1.1901 0.2639 0.9466 0.052 Uiso 0.50 1 calc PR .
H14C H 1.2004 0.3584 0.8336 0.052 Uiso 0.50 1 calc PR .
C15 C 0.7263(3) 0.3308(6) 0.4122(3) 0.0263(7) Uani 0.50 1 d P .
C16 C 0.6479(3) 0.1543(6) 0.4002(3) 0.0318(8) Uani 0.50 1 d P .
C17 C 0.5363(3) 0.1887(8) 0.3358(4) 0.0443(12) Uani 0.50 1 d P .
C18A C 0.5925(19) 0.2500 0.9386(17) 0.094(8) Uani 0.57(3) 2 d SP 1
H18A H 0.5882 0.2500 1.0164 0.113 Uiso 0.57(3) 2 calc SPR 1
Cl1A Cl 0.6490(4) 0.0479(9) 0.9134(4) 0.0880(16) Uani 0.50 1 d P 1
Cl2A Cl 0.4618(6) 0.2500 0.8845(16) 0.125(3) Uani 0.57(3) 2 d SP 1
C18B C 0.5861(18) 0.2500 0.9383(10) 0.046(5) Uani 0.43(3) 2 d SP 2
H18B H 0.5721 0.2500 1.0141 0.055 Uiso 0.43(3) 2 calc SPR 2
Cl1B Cl 0.6724(3) 0.0385(7) 0.9045(2) 0.0447(5) Uani 0.50 1 d P 2
Cl2B Cl 0.4574(7) 0.2500 0.8491(12) 0.118(3) Uani 0.43(3) 2 d SP 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
O3 O3 C11 75.72(13) 4_565 .
C1 N1 C2 123.5(2) . .
C1 N1 C13 116.18(19) . .
C2 N1 C13 120.32(19) . .
C2 N2 C3 118.7(2) . .
C11 N3 C1 125.7(2) . .
C11 N3 C12 117.8(2) . .
C1 N3 C12 116.48(19) . .
C5 O2 C14 117.94(19) . .
F3 F1 C15 103.3(3) 4_565 .
F3 F1 C16 68.2(3) 4_565 4_565
C15 F1 C16 40.6(2) . 4_565
F3 F1 F4 106.0(3) 4_565 4_565
C15 F1 F4 51.0(2) . 4_565
C16 F1 F4 49.2(2) 4_565 4_565
F4 F2 C15 79.2(7) 4_565 .
F4 F2 C16 68.2(7) 4_565 4_565
C15 F2 C16 40.0(2) . 4_565
F1 F3 C16 74.2(3) 4_565 .
F1 F3 C15 47.8(2) 4_565 4_565
C16 F3 C15 31.78(19) . 4_565
F2 F4 C16 88.2(8) 4_565 .
F2 F4 C15 76.5(7) 4_565 4_565
C16 F4 C15 41.4(2) . 4_565
F2 F4 F1 127.1(8) 4_565 4_565
C16 F4 F1 52.4(2) . 4_565
C15 F4 F1 50.6(2) 4_565 4_565
C17 F5 F6 101.3(8) 4_565 4_565
C17 F5 F5 73.7(5) 4_565 4_565
F6 F5 F5 156.0(4) 4_565 4_565
C17 F5 C17 37.8(5) 4_565 .
F6 F5 C17 134.7(6) 4_565 .
F5 F5 C17 35.9(3) 4_565 .
F5 F6 C17 36.6(4) 4_565 .
C17 F7 C17 35.7(4) 4_565 .
O1 C1 N1 121.9(2) . .
O1 C1 N3 121.5(2) . .
N1 C1 N3 116.6(2) . .
N2 C2 N1 116.0(2) . .
N2 C2 C10 124.6(2) . .
N1 C2 C10 119.4(2) . .
N2 C3 C4 116.1(2) . .
N2 C3 C8 122.6(2) . .
C4 C3 C8 121.3(2) . .
C5 C4 C3 119.8(2) . .
C5 C4 H4 120.1 . .
C3 C4 H4 120.1 . .
O2 C5 C4 124.8(2) . .
O2 C5 C6 115.4(2) . .
C4 C5 C6 119.8(2) . .
C7 C6 C5 121.4(2) . .
C7 C6 H6 119.3 . .
C5 C6 H6 119.3 . .
C6 C7 C8 121.3(2) . .
C6 C7 H7 119.4 . .
C8 C7 H7 119.4 . .
C3 C8 C7 116.4(2) . .
C3 C8 C9 116.6(2) . .
C7 C8 C9 126.1(2) . .
C3 C8 C9 116.6(2) . 4_565
C7 C8 C9 126.1(2) . 4_565
C9 C8 C9 18.0(4) . 4_565
C9 C9 C10 80.9(2) 4_565 .
C9 C9 C8 81.0(2) 4_565 .
C10 C9 C8 117.6(2) . .
C9 C9 C15 102.4(2) 4_565 .
C10 C9 C15 121.5(2) . .
C8 C9 C15 120.6(2) . .
C9 C9 C15 62.7(2) 4_565 4_565
C10 C9 C15 111.8(3) . 4_565
C8 C9 C15 111.1(3) . 4_565
C15 C9 C15 39.7(3) . 4_565
C9 C10 C9 18.3(4) . 4_565
C9 C10 C2 116.7(2) . .
C9 C10 C2 116.7(2) 4_565 .
C9 C10 C11 123.8(2) . .
C9 C10 C11 123.8(2) 4_565 .
C2 C10 C11 118.6(2) . .
O3 C11 O3 28.6(3) . 4_565
O3 C11 N3 118.2(2) . .
O3 C11 N3 118.2(2) 4_565 .
O3 C11 C10 123.4(2) . .
O3 C11 C10 123.4(2) 4_565 .
N3 C11 C10 116.2(2) . .
N3 C12 H12A 109.5 . .
N3 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N3 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N1 C13 H13A 109.5 . .
N1 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
N1 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O2 C14 H14A 109.5 . .
O2 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O2 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 C15 96.2(3) 4_565 4_565
C16 C15 F2 74.5(3) 4_565 .
C15 C15 F2 127.4(2) 4_565 .
C16 C15 F1 71.7(3) 4_565 .
C15 C15 F1 123.6(2) 4_565 .
F2 C15 F1 102.7(3) . .
C16 C15 F4 67.3(4) 4_565 4_565
C15 C15 F4 148.1(2) 4_565 4_565
F2 C15 F4 24.27(16) . 4_565
F1 C15 F4 78.5(3) . 4_565
C16 C15 C16 58.0(4) 4_565 .
C15 C15 C16 38.11(19) 4_565 .
F2 C15 C16 110.6(3) . .
F1 C15 C16 106.1(3) . .
F4 C15 C16 119.0(3) 4_565 .
C16 C15 C9 173.3(5) 4_565 .
C15 C15 C9 77.6(2) 4_565 .
F2 C15 C9 111.1(3) . .
F1 C15 C9 109.8(3) . .
F4 C15 C9 119.3(4) 4_565 .
C16 C15 C9 115.7(3) . .
C16 C15 C9 158.7(5) 4_565 4_565
C15 C15 C9 62.7(2) 4_565 4_565
F2 C15 C9 119.2(3) . 4_565
F1 C15 C9 117.0(3) . 4_565
F4 C15 C9 132.0(3) 4_565 4_565
C16 C15 C9 100.8(3) . 4_565
C9 C15 C9 14.9(4) . 4_565
C16 C15 F3 47.9(3) 4_565 4_565
C15 C15 F3 104.71(17) 4_565 4_565
F2 C15 F3 105.4(3) . 4_565
F1 C15 F3 28.82(15) . 4_565
F4 C15 F3 84.6(3) 4_565 4_565
C16 C15 F3 78.5(2) . 4_565
C9 C15 F3 131.1(2) . 4_565
C9 C15 F3 131.7(2) 4_565 4_565
C15 C16 C16 83.8(3) 4_565 4_565
C15 C16 F4 71.3(4) 4_565 .
C16 C16 F4 142.6(2) 4_565 .
C15 C16 F3 100.4(4) 4_565 .
C16 C16 F3 105.1(2) 4_565 .
F4 C16 F3 106.4(4) . .
C15 C16 F1 67.8(3) 4_565 4_565
C16 C16 F1 117.8(2) 4_565 4_565
F4 C16 F1 78.5(3) . 4_565
F3 C16 F1 37.61(17) . 4_565
C15 C16 F2 65.5(3) 4_565 4_565
C16 C16 F2 120.1(2) 4_565 4_565
F4 C16 F2 23.52(17) . 4_565
F3 C16 F2 129.2(4) . 4_565
F1 C16 F2 97.1(3) 4_565 4_565
C15 C16 C17 152.3(5) 4_565 .
C16 C16 C17 81.1(2) 4_565 .
F4 C16 C17 108.4(4) . .
F3 C16 C17 106.0(3) . .
F1 C16 C17 140.0(3) 4_565 .
F2 C16 C17 102.7(3) 4_565 .
C15 C16 C15 45.7(4) 4_565 .
C16 C16 C15 38.11(19) 4_565 .
F4 C16 C15 111.9(3) . .
F3 C16 C15 107.4(3) . .
F1 C16 C15 95.8(3) 4_565 .
F2 C16 C15 96.0(2) 4_565 .
C17 C16 C15 116.0(4) . .
C15 C16 C17 132.9(4) 4_565 4_565
C16 C16 C17 54.55(19) 4_565 4_565
F4 C16 C17 128.4(4) . 4_565
F3 C16 C17 110.2(3) . 4_565
F1 C16 C17 147.4(3) 4_565 4_565
F2 C16 C17 114.1(3) 4_565 4_565
C17 C16 C17 26.6(3) . 4_565
C15 C16 C17 90.3(3) . 4_565
F5 C17 C17 106.3(5) 4_565 4_565
F5 C17 F5 70.4(6) 4_565 .
C17 C17 F5 35.9(3) 4_565 .
F5 C17 F6 42.0(5) 4_565 .
C17 C17 F6 142.6(3) 4_565 .
F5 C17 F6 109.0(4) . .
F5 C17 F7 138.8(5) 4_565 .
C17 C17 F7 72.1(2) 4_565 .
F5 C17 F7 99.1(4) . .
F6 C17 F7 116.2(3) . .
F5 C17 C16 108.6(5) 4_565 .
C17 C17 C16 98.9(2) 4_565 .
F5 C17 C16 110.3(4) . .
F6 C17 C16 109.5(4) . .
F7 C17 C16 112.3(3) . .
F5 C17 C16 117.5(6) 4_565 4_565
C17 C17 C16 54.55(19) 4_565 4_565
F5 C17 C16 73.3(3) . 4_565
F6 C17 C16 146.8(4) . 4_565
F7 C17 C16 95.5(3) . 4_565
C16 C17 C16 44.3(3) . 4_565
Cl1A C18A Cl1A 120.9(14) 4_565 .
Cl1A C18A Cl2A 109.2(9) 4_565 .
Cl1A C18A Cl2A 109.2(9) . .
Cl1A C18A H18A 105.4 4_565 .
Cl1A C18A H18A 105.4 . .
Cl2A C18A H18A 105.4 . .
Cl2B C18B Cl1B 108.8(6) . 4_565
Cl2B C18B Cl1B 108.8(6) . .
Cl1B C18B Cl1B 102.1(10) 4_565 .
Cl2B C18B H18B 112.2 . .
Cl1B C18B H18B 112.2 4_565 .
Cl1B C18B H18B 112.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 O3 0.607(5) 4_565
O3 C11 1.229(3) .
N1 C1 1.372(3) .
N1 C2 1.392(3) .
N1 C13 1.472(3) .
N2 C2 1.306(3) .
N2 C3 1.357(3) .
N3 C11 1.384(3) .
N3 C1 1.387(3) .
N3 C12 1.472(3) .
O1 C1 1.218(3) .
O2 C5 1.359(3) .
O2 C14 1.431(3) .
F1 F3 0.888(3) 4_565
F1 C15 1.366(4) .
F1 C16 1.401(4) 4_565
F1 F4 1.733(5) 4_565
F2 F4 0.575(3) 4_565
F2 C15 1.360(5) .
F2 C16 1.440(5) 4_565
F3 F1 0.888(3) 4_565
F3 C16 1.351(4) .
F3 C15 1.793(4) 4_565
F4 F2 0.575(3) 4_565
F4 C16 1.338(6) .
F4 C15 1.374(6) 4_565
F4 F1 1.733(5) 4_565
F5 C17 0.811(5) 4_565
F5 F6 0.909(5) 4_565
F5 F5 1.302(9) 4_565
F5 C17 1.326(6) .
F6 F5 0.909(5) 4_565
F6 C17 1.332(6) .
F7 C17 1.379(5) 4_565
F7 C17 1.379(5) .
C2 C10 1.425(3) .
C3 C4 1.412(3) .
C3 C8 1.430(3) .
C4 C5 1.371(3) .
C4 H4 0.9500 .
C5 C6 1.415(4) .
C6 C7 1.355(4) .
C6 H6 0.9500 .
C7 C8 1.432(3) .
C7 H7 0.9500 .
C8 C9 1.437(4) .
C8 C9 1.437(4) 4_565
C9 C9 0.449(11) 4_565
C9 C10 1.412(3) .
C9 C15 1.548(4) .
C9 C15 1.702(5) 4_565
C10 C9 1.412(3) 4_565
C10 C11 1.470(3) .
C11 O3 1.229(3) 4_565
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 0.960(4) 4_565
C15 C15 1.114(8) 4_565
C15 F4 1.374(6) 4_565
C15 C16 1.547(5) .
C15 C9 1.702(5) 4_565
C15 F3 1.793(4) 4_565
C16 C15 0.960(5) 4_565
C16 C16 1.320(8) 4_565
C16 F1 1.401(4) 4_565
C16 F2 1.440(5) 4_565
C16 C17 1.540(5) .
C16 C17 1.867(6) 4_565
C17 F5 0.811(5) 4_565
C17 C17 0.846(10) 4_565
C17 C16 1.867(6) 4_565
C18A Cl1A 1.602(12) 4_565
C18A Cl1A 1.602(12) .
C18A Cl2A 1.68(2) .
C18A H18A 1.0000 .
C18B Cl2B 1.85(2) .
C18B Cl1B 1.876(14) 4_565
C18B Cl1B 1.876(14) .
C18B H18B 1.0000 .
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_4
C2 N1 C1 O1 180.0 . .
C13 N1 C1 O1 0.0 . .
C2 N1 C1 N3 0.0 . .
C13 N1 C1 N3 180.0 . .
C11 N3 C1 O1 180.0 . .
C12 N3 C1 O1 0.0 . .
C11 N3 C1 N1 0.0 . .
C12 N3 C1 N1 180.0 . .
C3 N2 C2 N1 180.0 . .
C3 N2 C2 C10 0.0 . .
C1 N1 C2 N2 180.0 . .
C13 N1 C2 N2 0.0 . .
C1 N1 C2 C10 0.0 . .
C13 N1 C2 C10 180.0 . .
C2 N2 C3 C4 180.0 . .
C2 N2 C3 C8 0.0 . .
N2 C3 C4 C5 180.0 . .
C8 C3 C4 C5 0.0 . .
C14 O2 C5 C4 0.0 . .
C14 O2 C5 C6 180.0 . .
C3 C4 C5 O2 180.0 . .
C3 C4 C5 C6 0.0 . .
O2 C5 C6 C7 180.0 . .
C4 C5 C6 C7 0.0 . .
C5 C6 C7 C8 0.0 . .
N2 C3 C8 C7 180.0 . .
C4 C3 C8 C7 0.0 . .
N2 C3 C8 C9 -10.1(2) . .
C4 C3 C8 C9 169.9(2) . .
N2 C3 C8 C9 10.1(2) . 4_565
C4 C3 C8 C9 -169.9(2) . 4_565
C6 C7 C8 C3 0.0 . .
C6 C7 C8 C9 -168.9(3) . .
C6 C7 C8 C9 168.9(3) . 4_565
C3 C8 C9 C9 94.54(12) . 4_565
C7 C8 C9 C9 -96.61(17) . 4_565
C3 C8 C9 C10 19.9(5) . .
C7 C8 C9 C10 -171.3(2) . .
C9 C8 C9 C10 -74.7(4) 4_565 .
C3 C8 C9 C15 -166.3(3) . .
C7 C8 C9 C15 2.6(5) . .
C9 C8 C9 C15 99.2(4) 4_565 .
C3 C8 C9 C15 150.5(2) . 4_565
C7 C8 C9 C15 -40.6(4) . 4_565
C9 C8 C9 C15 56.0(3) 4_565 4_565
C8 C9 C10 C9 74.8(4) . 4_565
C15 C9 C10 C9 -99.0(4) . 4_565
C15 C9 C10 C9 -55.6(3) 4_565 4_565
C9 C9 C10 C2 -94.65(12) 4_565 .
C8 C9 C10 C2 -19.9(5) . .
C15 C9 C10 C2 166.3(3) . .
C15 C9 C10 C2 -150.2(2) 4_565 .
C9 C9 C10 C11 96.19(16) 4_565 .
C8 C9 C10 C11 171.0(2) . .
C15 C9 C10 C11 -2.8(5) . .
C15 C9 C10 C11 40.6(4) 4_565 .
N2 C2 C10 C9 10.2(2) . .
N1 C2 C10 C9 -169.8(2) . .
N2 C2 C10 C9 -10.2(2) . 4_565
N1 C2 C10 C9 169.8(2) . 4_565
N2 C2 C10 C11 180.0 . .
N1 C2 C10 C11 0.0 . .
O3 O3 C11 N3 -97.85(10) 4_565 .
O3 O3 C11 C10 99.65(12) 4_565 .
C1 N3 C11 O3 -163.74(15) . .
C12 N3 C11 O3 16.26(15) . .
C1 N3 C11 O3 163.74(15) . 4_565
C12 N3 C11 O3 -16.26(15) . 4_565
C1 N3 C11 C10 0.0 . .
C12 N3 C11 C10 180.0 . .
C9 C10 C11 O3 -28.2(3) . .
C9 C10 C11 O3 -6.2(3) 4_565 .
C2 C10 C11 O3 162.82(16) . .
C9 C10 C11 O3 6.2(3) . 4_565
C9 C10 C11 O3 28.2(3) 4_565 4_565
C2 C10 C11 O3 -162.82(16) . 4_565
C9 C10 C11 N3 169.0(3) . .
C9 C10 C11 N3 -169.0(3) 4_565 .
C2 C10 C11 N3 0.0 . .
F4 F2 C15 C16 68.9(8) 4_565 4_565
F4 F2 C15 C15 154.8(7) 4_565 4_565
C16 F2 C15 C15 85.9(3) 4_565 4_565
F4 F2 C15 F1 2.3(8) 4_565 .
C16 F2 C15 F1 -66.6(3) 4_565 .
C16 F2 C15 F4 -68.9(8) 4_565 4_565
F4 F2 C15 C16 115.2(8) 4_565 .
C16 F2 C15 C16 46.3(4) 4_565 .
F4 F2 C15 C9 -114.9(8) 4_565 .
C16 F2 C15 C9 176.1(5) 4_565 .
F4 F2 C15 C9 -128.8(8) 4_565 4_565
C16 F2 C15 C9 162.3(5) 4_565 4_565
F4 F2 C15 F3 32.0(8) 4_565 4_565
C16 F2 C15 F3 -37.0(3) 4_565 4_565
F3 F1 C15 C16 30.3(4) 4_565 4_565
F4 F1 C15 C16 -69.7(4) 4_565 4_565
F3 F1 C15 C15 -54.9(3) 4_565 4_565
C16 F1 C15 C15 -85.1(3) 4_565 4_565
F4 F1 C15 C15 -154.8(3) 4_565 4_565
F3 F1 C15 F2 98.9(4) 4_565 .
C16 F1 C15 F2 68.7(4) 4_565 .
F4 F1 C15 F2 -1.0(4) 4_565 .
F3 F1 C15 F4 99.9(4) 4_565 4_565
C16 F1 C15 F4 69.7(4) 4_565 4_565
F3 F1 C15 C16 -17.2(4) 4_565 .
C16 F1 C15 C16 -47.5(4) 4_565 .
F4 F1 C15 C16 -117.1(3) 4_565 .
F3 F1 C15 C9 -142.8(4) 4_565 .
C16 F1 C15 C9 -173.1(5) 4_565 .
F4 F1 C15 C9 117.3(4) 4_565 .
F3 F1 C15 C9 -128.6(4) 4_565 4_565
C16 F1 C15 C9 -158.8(5) 4_565 4_565
F4 F1 C15 C9 131.5(4) 4_565 4_565
C16 F1 C15 F3 -30.3(4) 4_565 4_565
F4 F1 C15 F3 -99.9(4) 4_565 4_565
C9 C9 C15 C16 21(3) 4_565 4_565
C10 C9 C15 C16 107(3) . 4_565
C8 C9 C15 C16 -66(4) . 4_565
C15 C9 C15 C16 21(3) 4_565 4_565
C9 C9 C15 C15 0.000(1) 4_565 4_565
C10 C9 C15 C15 86.8(4) . 4_565
C8 C9 C15 C15 -86.8(4) . 4_565
C9 C9 C15 F2 -125.5(3) 4_565 .
C10 C9 C15 F2 -38.7(6) . .
C8 C9 C15 F2 147.6(4) . .
C15 C9 C15 F2 -125.5(3) 4_565 .
C9 C9 C15 F1 121.5(2) 4_565 .
C10 C9 C15 F1 -151.7(4) . .
C8 C9 C15 F1 34.7(5) . .
C15 C9 C15 F1 121.5(2) 4_565 .
C9 C9 C15 F4 -150.9(3) 4_565 4_565
C10 C9 C15 F4 -64.1(5) . 4_565
C8 C9 C15 F4 122.3(4) . 4_565
C15 C9 C15 F4 -150.9(3) 4_565 4_565
C9 C9 C15 C16 1.6(3) 4_565 .
C10 C9 C15 C16 88.4(5) . .
C8 C9 C15 C16 -85.2(5) . .
C15 C9 C15 C16 1.6(3) 4_565 .
C10 C9 C15 C9 86.8(4) . 4_565
C8 C9 C15 C9 -86.8(4) . 4_565
C15 C9 C15 C9 0.000(1) 4_565 4_565
C9 C9 C15 F3 98.8(4) 4_565 4_565
C10 C9 C15 F3 -174.4(3) . 4_565
C8 C9 C15 F3 12.0(7) . 4_565
C15 C9 C15 F3 98.8(4) 4_565 4_565
F2 F4 C16 C15 -71.5(8) 4_565 4_565
F1 F4 C16 C15 70.2(3) 4_565 4_565
F2 F4 C16 C16 -20.6(10) 4_565 4_565
C15 F4 C16 C16 50.9(4) 4_565 4_565
F1 F4 C16 C16 121.1(4) 4_565 4_565
F2 F4 C16 F3 -167.1(8) 4_565 .
C15 F4 C16 F3 -95.6(4) 4_565 .
F1 F4 C16 F3 -25.4(2) 4_565 .
F2 F4 C16 F1 -141.7(8) 4_565 4_565
C15 F4 C16 F1 -70.2(3) 4_565 4_565
C15 F4 C16 F2 71.5(8) 4_565 4_565
F1 F4 C16 F2 141.7(8) 4_565 4_565
F2 F4 C16 C17 79.2(8) 4_565 .
C15 F4 C16 C17 150.7(5) 4_565 .
F1 F4 C16 C17 -139.1(4) 4_565 .
F2 F4 C16 C15 -50.1(9) 4_565 .
C15 F4 C16 C15 21.5(2) 4_565 .
F1 F4 C16 C15 91.7(3) 4_565 .
F2 F4 C16 C17 59.0(9) 4_565 4_565
C15 F4 C16 C17 130.5(5) 4_565 4_565
F1 F4 C16 C17 -159.3(4) 4_565 4_565
F1 F3 C16 C15 -29.8(4) 4_565 4_565
F1 F3 C16 C16 -116.2(3) 4_565 4_565
C15 F3 C16 C16 -86.4(4) 4_565 4_565
F1 F3 C16 F4 43.6(4) 4_565 .
C15 F3 C16 F4 73.4(4) 4_565 .
C15 F3 C16 F1 29.8(4) 4_565 4_565
F1 F3 C16 F2 37.0(5) 4_565 4_565
C15 F3 C16 F2 66.8(4) 4_565 4_565
F1 F3 C16 C17 158.9(4) 4_565 .
C15 F3 C16 C17 -171.3(6) 4_565 .
F1 F3 C16 C15 -76.5(4) 4_565 .
C15 F3 C16 C15 -46.7(4) 4_565 .
F1 F3 C16 C17 -173.4(4) 4_565 4_565
C15 F3 C16 C17 -143.6(5) 4_565 4_565
C16 C15 C16 C15 180.0 4_565 4_565
F2 C15 C16 C15 124.8(3) . 4_565
F1 C15 C16 C15 -124.5(2) . 4_565
F4 C15 C16 C15 150.0(2) 4_565 4_565
C9 C15 C16 C15 -2.5(4) . 4_565
C9 C15 C16 C15 -2.1(4) 4_565 4_565
F3 C15 C16 C15 -132.8(2) 4_565 4_565
C15 C15 C16 C16 180.0 4_565 4_565
F2 C15 C16 C16 -55.2(3) . 4_565
F1 C15 C16 C16 55.5(2) . 4_565
F4 C15 C16 C16 -30.0(2) 4_565 4_565
C9 C15 C16 C16 177.5(4) . 4_565
C9 C15 C16 C16 177.9(4) 4_565 4_565
F3 C15 C16 C16 47.2(2) 4_565 4_565
C16 C15 C16 F4 151.1(2) 4_565 .
C15 C15 C16 F4 -28.9(2) 4_565 .
F2 C15 C16 F4 95.9(4) . .
F1 C15 C16 F4 -153.4(3) . .
F4 C15 C16 F4 121.1(4) 4_565 .
C9 C15 C16 F4 -31.5(4) . .
C9 C15 C16 F4 -31.1(4) 4_565 .
F3 C15 C16 F4 -161.8(3) 4_565 .
C16 C15 C16 F3 -92.4(4) 4_565 .
C15 C15 C16 F3 87.6(4) 4_565 .
F2 C15 C16 F3 -147.6(3) . .
F1 C15 C16 F3 -36.9(4) . .
F4 C15 C16 F3 -122.4(4) 4_565 .
C9 C15 C16 F3 85.0(3) . .
C9 C15 C16 F3 85.4(3) 4_565 .
F3 C15 C16 F3 -45.3(3) 4_565 .
C16 C15 C16 F1 -129.1(2) 4_565 4_565
C15 C15 C16 F1 50.9(2) 4_565 4_565
F2 C15 C16 F1 175.8(3) . 4_565
F1 C15 C16 F1 -73.5(3) . 4_565
F4 C15 C16 F1 -159.0(3) 4_565 4_565
C9 C15 C16 F1 48.4(3) . 4_565
C9 C15 C16 F1 48.8(3) 4_565 4_565
F3 C15 C16 F1 -81.9(2) 4_565 4_565
C16 C15 C16 F2 133.1(2) 4_565 4_565
C15 C15 C16 F2 -46.9(2) 4_565 4_565
F2 C15 C16 F2 78.0(3) . 4_565
F1 C15 C16 F2 -171.3(3) . 4_565
F4 C15 C16 F2 103.2(4) 4_565 4_565
C9 C15 C16 F2 -49.4(3) . 4_565
C9 C15 C16 F2 -49.0(3) 4_565 4_565
F3 C15 C16 F2 -179.7(3) 4_565 4_565
C16 C15 C16 C17 25.9(5) 4_565 .
C15 C15 C16 C17 -154.1(5) 4_565 .
F2 C15 C16 C17 -29.3(4) . .
F1 C15 C16 C17 81.4(4) . .
F4 C15 C16 C17 -4.1(5) 4_565 .
C9 C15 C16 C17 -156.7(3) . .
C9 C15 C16 C17 -156.2(3) 4_565 .
F3 C15 C16 C17 73.0(3) 4_565 .
C16 C15 C16 C17 18.9(4) 4_565 4_565
C15 C15 C16 C17 -161.1(4) 4_565 4_565
F2 C15 C16 C17 -36.3(3) . 4_565
F1 C15 C16 C17 74.4(3) . 4_565
F4 C15 C16 C17 -11.1(4) 4_565 4_565
C9 C15 C16 C17 -163.7(3) . 4_565
C9 C15 C16 C17 -163.2(2) 4_565 4_565
F3 C15 C16 C17 66.0(2) 4_565 4_565
C17 F5 C17 F5 180.000(3) 4_565 4_565
F6 F5 C17 F5 -145.5(5) 4_565 4_565
F6 F5 C17 C17 34.5(5) 4_565 4_565
F5 F5 C17 C17 180.000(3) 4_565 4_565
C17 F5 C17 F6 -163.1(3) 4_565 .
F6 F5 C17 F6 -128.6(7) 4_565 .
F5 F5 C17 F6 16.9(3) 4_565 .
C17 F5 C17 F7 -41.2(5) 4_565 .
F6 F5 C17 F7 -6.8(7) 4_565 .
F5 F5 C17 F7 138.8(5) 4_565 .
C17 F5 C17 C16 76.7(6) 4_565 .
F6 F5 C17 C16 111.1(7) 4_565 .
F5 F5 C17 C16 -103.3(6) 4_565 .
C17 F5 C17 C16 51.8(4) 4_565 4_565
F6 F5 C17 C16 86.2(6) 4_565 4_565
F5 F5 C17 C16 -128.2(4) 4_565 4_565
F5 F6 C17 C17 -40.5(6) 4_565 4_565
F5 F6 C17 F5 -24.1(4) 4_565 .
F5 F6 C17 F7 -135.0(7) 4_565 .
F5 F6 C17 C16 96.6(6) 4_565 .
F5 F6 C17 C16 64.3(8) 4_565 4_565
C17 F7 C17 F5 94.6(10) 4_565 4_565
C17 F7 C17 F5 24.0(3) 4_565 .
C17 F7 C17 F6 140.5(3) 4_565 .
C17 F7 C17 C16 -92.5(3) 4_565 .
C17 F7 C17 C16 -50.0(2) 4_565 4_565
C15 C16 C17 F5 -168.7(10) 4_565 4_565
C16 C16 C17 F5 -110.7(6) 4_565 4_565
F4 C16 C17 F5 106.6(6) . 4_565
F3 C16 C17 F5 -7.4(7) . 4_565
F1 C16 C17 F5 12.6(9) 4_565 4_565
F2 C16 C17 F5 130.3(6) 4_565 4_565
C15 C16 C17 F5 -126.5(6) . 4_565
C17 C16 C17 F5 -110.7(6) 4_565 4_565
C15 C16 C17 C17 -58.1(10) 4_565 4_565
C16 C16 C17 C17 0.0 4_565 4_565
F4 C16 C17 C17 -142.8(2) . 4_565
F3 C16 C17 C17 103.3(3) . 4_565
F1 C16 C17 C17 123.3(5) 4_565 4_565
F2 C16 C17 C17 -119.1(2) 4_565 4_565
C15 C16 C17 C17 -15.8(3) . 4_565
C15 C16 C17 F5 -93.3(10) 4_565 .
C16 C16 C17 F5 -35.3(4) 4_565 .
F4 C16 C17 F5 -178.0(4) . .
F3 C16 C17 F5 68.0(5) . .
F1 C16 C17 F5 88.0(6) 4_565 .
F2 C16 C17 F5 -154.3(4) 4_565 .
C15 C16 C17 F5 -51.1(5) . .
C17 C16 C17 F5 -35.3(4) 4_565 .
C15 C16 C17 F6 146.7(9) 4_565 .
C16 C16 C17 F6 -155.2(4) 4_565 .
F4 C16 C17 F6 62.0(5) . .
F3 C16 C17 F6 -51.9(5) . .
F1 C16 C17 F6 -32.0(7) 4_565 .
F2 C16 C17 F6 85.7(4) 4_565 .
C15 C16 C17 F6 -171.1(3) . .
C17 C16 C17 F6 -155.2(4) 4_565 .
C15 C16 C17 F7 16.2(11) 4_565 .
C16 C16 C17 F7 74.2(3) 4_565 .
F4 C16 C17 F7 -68.5(4) . .
F3 C16 C17 F7 177.5(3) . .
F1 C16 C17 F7 -162.5(4) 4_565 .
F2 C16 C17 F7 -44.8(4) 4_565 .
C15 C16 C17 F7 58.4(4) . .
C17 C16 C17 F7 74.2(3) 4_565 .
C15 C16 C17 C16 -58.1(10) 4_565 4_565
F4 C16 C17 C16 -142.8(2) . 4_565
F3 C16 C17 C16 103.3(3) . 4_565
F1 C16 C17 C16 123.3(5) 4_565 4_565
F2 C16 C17 C16 -119.1(2) 4_565 4_565
C15 C16 C17 C16 -15.8(3) . 4_565
C17 C16 C17 C16 0.000(1) 4_565 4_565
