#------------------------------------------------------------------------------
#$Date: 2021-11-01 04:06:57 +0200 (Mon, 01 Nov 2021) $
#$Revision: 270183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/38/7243810.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_7243810
loop_
_publ_author_name
'Shchegolkov, Evgeny V.'
'Burgart, Yanina V.'
'Matsneva, Daria A.'
'Borisevich, Sophia S.'
'Kadyrova, Renata A.'
'Orshanskaya, Iana R.'
'Zarubaev, Vladimir V.'
'Saloutin, Victor I.'
_publ_section_title
;
 Polyfluoroalkylated antipyrines in Pd-catalyzed transformations
;
_journal_issue                   56
_journal_name_full               'RSC Advances'
_journal_page_first              35174
_journal_page_last               35181
_journal_paper_doi               10.1039/D1RA06967E
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C18 H12 F6 N2 O'
_chemical_formula_sum            'C18 H12 F6 N2 O'
_chemical_formula_weight         386.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-17 deposited with the CCDC.	2021-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                93.734(6)
_cell_angle_beta                 90.935(6)
_cell_angle_gamma                95.221(6)
_cell_formula_units_Z            4
_cell_length_a                   8.6416(7)
_cell_length_b                   11.0188(9)
_cell_length_c                   18.0722(14)
_cell_measurement_reflns_used    2223
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.5630
_cell_measurement_theta_min      3.7390
_cell_volume                     1709.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00   5.00   1.00   50.00    --   22.52 -87.00  20.00   44
  2  ω    -11.00  14.00   1.00   50.00    --   22.52  87.00 137.00   25
  3  ω    -60.00  39.00   1.00   50.00    --  -23.92  87.00 137.00   99
  4  ω    -26.00   0.00   1.00   50.00    --  -23.92 -87.00  20.00   26
  5  ω     35.00  98.00   1.00   50.00    --   22.52 178.00 150.00   63
  6  ω    -25.00  64.00   1.00   50.00    --   22.52 -99.00 -30.00   89
  7  ω     -3.00  95.00   1.00   50.00    --   22.52  38.00 -60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0896
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15737
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.276
_diffrn_reflns_theta_min         3.612
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     584
_refine_ls_number_reflns         8397
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0565P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1816
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3326
_reflns_number_total             8397
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra06967e2.cif
_cod_data_source_block           exp_1081
_cod_database_code               7243810
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11B-C10B
 1.4 with sigma of 0.02
 C9-C8B
 1.4 with sigma of 0.02
 C8B-C7B
 1.4 with sigma of 0.02
 C10B-C9
 1.4 with sigma of 0.02
 C7B-C6
 1.4 with sigma of 0.02
 C11B-C6
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F4A) \\sim Ueq, Uanis(F6B) \\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F5B)
\\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F4B) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C10B) \\sim Ueq, Uanis(C11B) \\sim Ueq, Uanis(C8B) \\sim Ueq, Uanis(C7B)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: C7(0.93) H7(0.93) C8(0.93) H8(0.93) C10(0.93) H10(0.93) C11(0.93)
 H11(0.93) F4A(0.4) F5A(0.4) F6A(0.4) F4B(0.6) F5B(0.6) F6B(0.6) C8B(0.07)
 H8B(0.07) C7B(0.07) H7B(0.07) C11B(0.07) H11B(0.07) C10B(0.07) H10B(0.07)
5.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C17A(H17A), C8B(H8B), C7B(H7B), C11B(H11B), C10B(H10B)
5.b Idealised Me refined as rotating group:
 C01E(H01A,H01B,H01C), C019(H01D,H01E,H01F)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3671(3) 0.7578(3) 0.57570(15) 0.1446(11) Uani 1 1 d . . . . .
F2 F 0.2560(4) 0.5835(3) 0.59562(17) 0.1525(12) Uani 1 1 d . . . . .
F3 F 0.4172(3) 0.6755(3) 0.67389(15) 0.1368(10) Uani 1 1 d . . . . .
F4 F 0.2728(3) 1.2235(2) 0.39474(12) 0.1226(9) Uani 1 1 d . . . . .
F5 F 0.3564(3) 1.33813(19) 0.48854(11) 0.0949(6) Uani 1 1 d . . . . .
F6 F 0.1149(3) 1.3180(2) 0.46032(15) 0.1295(10) Uani 1 1 d . . . . .
O1 O -0.0739(3) 0.96278(18) 0.72838(11) 0.0689(6) Uani 1 1 d . . . . .
N1 N -0.0036(3) 0.7711(2) 0.74933(13) 0.0595(6) Uani 1 1 d . . . . .
N2 N 0.0920(3) 0.6887(2) 0.71604(14) 0.0639(7) Uani 1 1 d . . . . .
C1 C 0.2424(4) 1.2550(3) 0.4641(2) 0.0777(10) Uani 1 1 d . . . . .
C01A C 0.3034(5) 0.6925(4) 0.6263(2) 0.0900(12) Uani 1 1 d . . . . .
C01E C 0.1540(4) 0.6024(3) 0.7651(2) 0.0862(11) Uani 1 1 d . . . . .
H01A H 0.228226 0.645720 0.799606 0.129 Uiso 1 1 calc R U . . .
H01B H 0.203660 0.541828 0.735890 0.129 Uiso 1 1 calc R U . . .
H01C H 0.070421 0.563207 0.791776 0.129 Uiso 1 1 calc R U . . .
C3 C 0.1737(4) 0.7513(3) 0.66428(16) 0.0599(8) Uani 1 1 d . . . . .
C4 C 0.1254(3) 0.8650(3) 0.65766(15) 0.0564(7) Uani 1 1 d . . . . .
C5 C 0.0068(3) 0.8790(3) 0.71375(15) 0.0540(7) Uani 1 1 d . . . . .
C6 C 0.1629(3) 0.9604(3) 0.60550(16) 0.0575(7) Uani 1 1 d D . . . .
C7 C 0.1720(4) 1.0811(3) 0.63313(19) 0.0617(8) Uani 0.93 1 d . . P A 1
H7 H 0.149(3) 1.102(3) 0.6858(17) 0.066(9) Uiso 0.93 1 d . . P . .
C8 C 0.1999(4) 1.1763(3) 0.58734(18) 0.0646(9) Uani 0.93 1 d . . P A 1
H8 H 0.209(4) 1.268(3) 0.6106(17) 0.081(10) Uiso 0.93 1 d . . P . .
C9 C 0.2180(3) 1.1522(3) 0.51274(17) 0.0643(8) Uani 1 1 d D . . . .
C10 C 0.2091(4) 1.0316(4) 0.4832(2) 0.0696(10) Uani 0.93 1 d . . P A 1
H10 H 0.212(4) 1.019(3) 0.4303(19) 0.076(10) Uiso 0.93 1 d . . P . .
C11 C 0.1811(4) 0.9366(4) 0.52882(19) 0.0645(9) Uani 0.93 1 d . . P A 1
H11 H 0.167(4) 0.853(3) 0.5086(16) 0.070(10) Uiso 0.93 1 d . . P . .
C12 C -0.1270(4) 0.7290(3) 0.79610(16) 0.0569(7) Uani 1 1 d . . . . .
C13 C -0.2414(4) 0.6419(3) 0.76935(19) 0.0757(9) Uani 1 1 d . . . . .
H13 H -0.239065 0.609272 0.720654 0.091 Uiso 1 1 calc R U . . .
C14 C -0.3591(5) 0.6032(3) 0.8147(2) 0.0911(11) Uani 1 1 d . . . . .
H14 H -0.437312 0.544744 0.796504 0.109 Uiso 1 1 calc R U . . .
C15 C -0.3620(5) 0.6504(4) 0.8869(2) 0.0941(13) Uani 1 1 d . . . . .
H15 H -0.441073 0.623438 0.917790 0.113 Uiso 1 1 calc R U . . .
C16 C -0.2478(6) 0.7371(4) 0.9128(2) 0.0958(13) Uani 1 1 d . . . . .
H16 H -0.250806 0.770288 0.961390 0.115 Uiso 1 1 calc R U . . .
C17 C -0.1285(5) 0.7761(3) 0.86822(18) 0.0757(10) Uani 1 1 d . . . . .
H17 H -0.049763 0.833785 0.886700 0.091 Uiso 1 1 calc R U . . .
F1A F 0.3014(3) -0.10239(17) 0.84659(12) 0.0995(7) Uani 1 1 d . . . . .
F2A F 0.3104(3) 0.02381(18) 0.94204(11) 0.0944(7) Uani 1 1 d . . . . .
F3A F 0.5194(2) -0.03737(17) 0.89954(12) 0.0960(7) Uani 1 1 d . . . . .
O002 O 0.3344(3) 0.36866(18) 0.75017(11) 0.0711(6) Uani 1 1 d . . . . .
N1A N 0.5013(3) 0.2159(2) 0.74599(12) 0.0574(6) Uani 1 1 d . . . . .
N2A N 0.5213(3) 0.1117(2) 0.78480(13) 0.0598(6) Uani 1 1 d . . . . .
C00V C 0.3817(4) -0.0037(3) 0.8794(2) 0.0687(9) Uani 1 1 d . . . . .
C1A C -0.2610(5) 0.3071(4) 0.9704(2) 0.0785(10) Uani 1 1 d . . . . .
C3A C 0.3960(4) 0.1004(2) 0.83035(15) 0.0546(7) Uani 1 1 d . . . . .
C4A C 0.3025(3) 0.1937(2) 0.82617(14) 0.0511(7) Uani 1 1 d . . . . .
C5A C 0.3729(3) 0.2712(3) 0.77105(15) 0.0556(7) Uani 1 1 d . . . . .
C6A C 0.1601(3) 0.2204(2) 0.86510(15) 0.0534(7) Uani 1 1 d . . . . .
C7A C 0.0424(4) 0.1298(3) 0.87721(17) 0.0609(8) Uani 1 1 d . . . . .
H7A H 0.052(3) 0.044(3) 0.8572(14) 0.067(8) Uiso 1 1 d . . . . .
C8A C -0.0922(4) 0.1572(3) 0.91228(17) 0.0639(8) Uani 1 1 d . . . . .
H8A H -0.174(4) 0.095(3) 0.9191(15) 0.069(9) Uiso 1 1 d . . . . .
C9A C -0.1138(4) 0.2770(3) 0.93414(16) 0.0613(8) Uani 1 1 d . . . . .
C10A C -0.0013(4) 0.3681(3) 0.92012(17) 0.0679(9) Uani 1 1 d . . . . .
H10A H -0.006(4) 0.448(3) 0.935(2) 0.111(13) Uiso 1 1 d . . . . .
C11A C 0.1348(4) 0.3410(3) 0.88670(17) 0.0619(8) Uani 1 1 d . . . . .
H11A H 0.215(3) 0.405(2) 0.8782(14) 0.057(8) Uiso 1 1 d . . . . .
C12A C 0.6276(4) 0.2708(3) 0.70563(15) 0.0568(7) Uani 1 1 d . . . . .
C13A C 0.7799(4) 0.2637(3) 0.72910(17) 0.0714(9) Uani 1 1 d . . . . .
H13A H 0.801305 0.221366 0.770379 0.086 Uiso 1 1 calc R U . . .
C14A C 0.8985(4) 0.3199(3) 0.6907(2) 0.0810(10) Uani 1 1 d . . . . .
H14A H 1.000948 0.315509 0.706034 0.097 Uiso 1 1 calc R U . . .
C15A C 0.8675(5) 0.3827(3) 0.6296(2) 0.0847(11) Uani 1 1 d . . . . .
H15A H 0.948780 0.419620 0.603515 0.102 Uiso 1 1 calc R U . . .
C16A C 0.7164(5) 0.3908(3) 0.60711(18) 0.0811(10) Uani 1 1 d . . . . .
H16A H 0.695565 0.434425 0.566321 0.097 Uiso 1 1 calc R U . . .
C17A C 0.5954(4) 0.3344(3) 0.64477(17) 0.0712(9) Uani 1 1 d . . . . .
H17A H 0.493135 0.339269 0.629304 0.085 Uiso 1 1 calc R U . . .
C019 C 0.5674(4) 0.0053(3) 0.73807(19) 0.0827(10) Uani 1 1 d . . . . .
H01D H 0.485247 -0.022502 0.702928 0.124 Uiso 1 1 calc R U . . .
H01E H 0.586659 -0.059517 0.769071 0.124 Uiso 1 1 calc R U . . .
H01F H 0.660110 0.029136 0.712077 0.124 Uiso 1 1 calc R U . . .
F4A F -0.2922(16) 0.4143(11) 0.9650(10) 0.140(4) Uani 0.4 1 d . U P B 1
F5A F -0.2289(12) 0.3120(16) 1.0484(4) 0.135(4) Uani 0.4 1 d . U P B 1
F6A F -0.3676(13) 0.2266(14) 0.9635(9) 0.133(6) Uani 0.4 1 d . U P B 1
F4B F -0.3657(6) 0.3399(7) 0.9166(3) 0.1069(15) Uani 0.6 1 d . U P B 2
F5B F -0.3430(13) 0.2174(8) 0.9976(6) 0.140(5) Uani 0.6 1 d . U P B 2
F6B F -0.2501(7) 0.3984(9) 1.0166(6) 0.132(3) Uani 0.6 1 d . U P B 2
C8B C 0.077(3) 1.144(3) 0.5540(17) 0.045(8) Uani 0.07 1 d D U P A 2
H8B H 0.005873 1.201817 0.550226 0.054 Uiso 0.07 1 calc R U P A 2
C7B C 0.047(4) 1.045(3) 0.601(2) 0.077(13) Uani 0.07 1 d D U P A 2
H7B H -0.044195 1.035833 0.627537 0.092 Uiso 0.07 1 calc R U P A 2
C11B C 0.305(3) 0.990(4) 0.576(2) 0.073(13) Uani 0.07 1 d D U P A 2
H11B H 0.383760 0.939445 0.584593 0.087 Uiso 0.07 1 calc R U P A 2
C10B C 0.341(4) 1.090(4) 0.533(3) 0.084(15) Uani 0.07 1 d D U P A 2
H10B H 0.441742 1.112735 0.519834 0.101 Uiso 0.07 1 calc R U P 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 0.0033 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'
F F 0.0171 0.0103 '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'
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
_geom_angle_publ_flag
N2 N1 C12 120.3(2) . . ?
C5 N1 N2 110.7(2) . . ?
C5 N1 C12 126.1(2) . . ?
N1 N2 C01E 115.9(2) . . ?
C3 N2 N1 105.8(2) . . ?
C3 N2 C01E 125.9(3) . . ?
F4 C1 F5 106.6(3) . . ?
F4 C1 F6 105.1(3) . . ?
F4 C1 C9 115.0(3) . . ?
F5 C1 F6 104.6(3) . . ?
F5 C1 C9 113.0(3) . . ?
F6 C1 C9 111.7(3) . . ?
F1 C01A F2 108.4(4) . . ?
F1 C01A F3 106.1(4) . . ?
F1 C01A C3 112.8(3) . . ?
F2 C01A F3 105.8(3) . . ?
F2 C01A C3 111.6(4) . . ?
F3 C01A C3 111.6(3) . . ?
N2 C01E H01A 109.5 . . ?
N2 C01E H01B 109.5 . . ?
N2 C01E H01C 109.5 . . ?
H01A C01E H01B 109.5 . . ?
H01A C01E H01C 109.5 . . ?
H01B C01E H01C 109.5 . . ?
N2 C3 C01A 118.4(3) . . ?
N2 C3 C4 112.1(2) . . ?
C4 C3 C01A 129.4(3) . . ?
C3 C4 C5 105.8(3) . . ?
C3 C4 C6 133.0(3) . . ?
C5 C4 C6 121.0(2) . . ?
O1 C5 N1 123.8(3) . . ?
O1 C5 C4 130.9(3) . . ?
N1 C5 C4 105.3(2) . . ?
C7 C6 C4 117.8(3) . . ?
C7 C6 C11 118.1(3) . . ?
C11 C6 C4 124.0(3) . . ?
C7B C6 C4 113.6(14) . . ?
C11B C6 C4 126.1(18) . . ?
C11B C6 C7B 119(2) . . ?
C6 C7 H7 120.3(18) . . ?
C6 C7 C8 121.5(3) . . ?
C8 C7 H7 118.0(18) . . ?
C7 C8 H8 119.6(17) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.3(18) . . ?
C8 C9 C1 119.4(3) . . ?
C8 C9 C10 119.9(3) . . ?
C10 C9 C1 120.7(3) . . ?
C8B C9 C1 117.1(13) . . ?
C10B C9 C1 120.6(17) . . ?
C10B C9 C8B 120(2) . . ?
C9 C10 H10 117.0(19) . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 123(2) . . ?
C6 C11 H11 118.4(18) . . ?
C10 C11 C6 120.5(4) . . ?
C10 C11 H11 121.0(18) . . ?
C13 C12 N1 120.5(3) . . ?
C13 C12 C17 120.4(3) . . ?
C17 C12 N1 119.1(3) . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 120.9(4) . . ?
C17 C16 H16 119.5 . . ?
C12 C17 C16 119.2(4) . . ?
C12 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
N2A N1A C12A 120.0(2) . . ?
C5A N1A N2A 110.5(2) . . ?
C5A N1A C12A 126.6(2) . . ?
N1A N2A C019 114.6(2) . . ?
C3A N2A N1A 105.0(2) . . ?
C3A N2A C019 121.1(3) . . ?
F1A C00V C3A 112.1(3) . . ?
F2A C00V F1A 106.9(3) . . ?
F2A C00V F3A 105.9(3) . . ?
F2A C00V C3A 112.2(3) . . ?
F3A C00V F1A 106.9(3) . . ?
F3A C00V C3A 112.3(3) . . ?
F4A C1A C9A 114.4(5) . . ?
F4A C1A F5A 99.0(9) . . ?
F5A C1A C9A 105.7(5) . . ?
F6A C1A C9A 114.9(7) . . ?
F6A C1A F4A 117.9(10) . . ?
F6A C1A F5A 101.5(8) . . ?
F4B C1A C9A 109.5(3) . . ?
F5B C1A C9A 116.2(5) . . ?
F5B C1A F4B 100.5(6) . . ?
F6B C1A C9A 116.1(4) . . ?
F6B C1A F4B 103.0(6) . . ?
F6B C1A F5B 109.6(6) . . ?
N2A C3A C00V 118.5(3) . . ?
C4A C3A N2A 112.9(3) . . ?
C4A C3A C00V 128.5(3) . . ?
C3A C4A C5A 105.3(3) . . ?
C3A C4A C6A 131.8(3) . . ?
C5A C4A C6A 122.9(2) . . ?
O002 C5A N1A 124.2(3) . . ?
O002 C5A C4A 129.6(3) . . ?
N1A C5A C4A 106.1(2) . . ?
C7A C6A C4A 122.1(3) . . ?
C7A C6A C11A 117.6(3) . . ?
C11A C6A C4A 120.1(3) . . ?
C6A C7A H7A 119.6(17) . . ?
C8A C7A C6A 121.2(3) . . ?
C8A C7A H7A 119.1(17) . . ?
C7A C8A H8A 120.8(18) . . ?
C7A C8A C9A 120.1(3) . . ?
C9A C8A H8A 119.0(18) . . ?
C8A C9A C1A 120.2(3) . . ?
C10A C9A C1A 120.4(3) . . ?
C10A C9A C8A 119.4(3) . . ?
C9A C10A H10A 124(3) . . ?
C9A C10A C11A 120.7(3) . . ?
C11A C10A H10A 115(3) . . ?
C6A C11A H11A 118.8(16) . . ?
C10A C11A C6A 120.9(3) . . ?
C10A C11A H11A 120.4(16) . . ?
C13A C12A N1A 120.3(3) . . ?
C17A C12A N1A 119.1(3) . . ?
C17A C12A C13A 120.6(3) . . ?
C12A C13A H13A 120.4 . . ?
C14A C13A C12A 119.1(3) . . ?
C14A C13A H13A 120.4 . . ?
C13A C14A H14A 119.7 . . ?
C13A C14A C15A 120.7(3) . . ?
C15A C14A H14A 119.7 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A C14A 120.0(4) . . ?
C16A C15A H15A 120.0 . . ?
C15A C16A H16A 119.9 . . ?
C15A C16A C17A 120.3(3) . . ?
C17A C16A H16A 119.9 . . ?
C12A C17A H17A 120.3 . . ?
C16A C17A C12A 119.4(3) . . ?
C16A C17A H17A 120.3 . . ?
N2A C019 H01D 109.5 . . ?
N2A C019 H01E 109.5 . . ?
N2A C019 H01F 109.5 . . ?
H01D C019 H01E 109.5 . . ?
H01D C019 H01F 109.5 . . ?
H01E C019 H01F 109.5 . . ?
C9 C8B H8B 120.4 . . ?
C7B C8B C9 119(3) . . ?
C7B C8B H8B 120.4 . . ?
C6 C7B H7B 121.3 . . ?
C8B C7B C6 117(3) . . ?
C8B C7B H7B 121.3 . . ?
C6 C11B H11B 117.9 . . ?
C6 C11B C10B 124(3) . . ?
C10B C11B H11B 117.9 . . ?
C9 C10B C11B 117(3) . . ?
C9 C10B H10B 121.7 . . ?
C11B C10B H10B 121.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C01A 1.299(4) . ?
F2 C01A 1.317(5) . ?
F3 C01A 1.330(4) . ?
F4 C1 1.315(4) . ?
F5 C1 1.332(4) . ?
F6 C1 1.357(4) . ?
O1 C5 1.225(3) . ?
N1 N2 1.396(3) . ?
N1 C5 1.385(3) . ?
N1 C12 1.435(4) . ?
N2 C01E 1.471(4) . ?
N2 C3 1.366(4) . ?
C1 C9 1.481(4) . ?
C01A C3 1.498(4) . ?
C01E H01A 0.9600 . ?
C01E H01B 0.9600 . ?
C01E H01C 0.9600 . ?
C3 C4 1.368(4) . ?
C4 C5 1.464(4) . ?
C4 C6 1.475(4) . ?
C6 C7 1.384(4) . ?
C6 C11 1.408(4) . ?
C6 C7B 1.433(19) . ?
C6 C11B 1.370(19) . ?
C7 H7 0.99(3) . ?
C7 C8 1.384(4) . ?
C8 H8 1.07(3) . ?
C8 C9 1.371(4) . ?
C9 C10 1.395(5) . ?
C9 C8B 1.440(18) . ?
C9 C10B 1.374(19) . ?
C10 H10 0.96(3) . ?
C10 C11 1.381(5) . ?
C11 H11 0.97(3) . ?
C12 C13 1.372(4) . ?
C12 C17 1.372(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.364(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(5) . ?
C17 H17 0.9300 . ?
F1A C00V 1.335(4) . ?
F2A C00V 1.329(4) . ?
F3A C00V 1.331(4) . ?
O002 C5A 1.233(3) . ?
N1A N2A 1.406(3) . ?
N1A C5A 1.383(3) . ?
N1A C12A 1.433(4) . ?
N2A C3A 1.372(4) . ?
N2A C019 1.488(3) . ?
C00V C3A 1.492(4) . ?
C1A C9A 1.494(5) . ?
C1A F4A 1.245(8) . ?
C1A F5A 1.430(9) . ?
C1A F6A 1.218(11) . ?
C1A F4B 1.403(6) . ?
C1A F5B 1.292(9) . ?
C1A F6B 1.260(6) . ?
C3A C4A 1.369(4) . ?
C4A C5A 1.458(4) . ?
C4A C6A 1.471(4) . ?
C6A C7A 1.389(4) . ?
C6A C11A 1.398(4) . ?
C7A H7A 1.00(3) . ?
C7A C8A 1.382(4) . ?
C8A H8A 0.96(3) . ?
C8A C9A 1.383(4) . ?
C9A C10A 1.371(4) . ?
C10A H10A 0.91(3) . ?
C10A C11A 1.378(4) . ?
C11A H11A 0.97(3) . ?
C12A C13A 1.387(4) . ?
C12A C17A 1.380(4) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.371(5) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.376(5) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.373(5) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.379(5) . ?
C17A H17A 0.9300 . ?
C019 H01D 0.9600 . ?
C019 H01E 0.9600 . ?
C019 H01F 0.9600 . ?
C8B H8B 0.9300 . ?
C8B C7B 1.432(19) . ?
C7B H7B 0.9300 . ?
C11B H11B 0.9300 . ?
C11B C10B 1.40(2) . ?
C10B H10B 0.9300 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C01A C3 N2 176.6(3) . . . . ?
F1 C01A C3 C4 -6.6(6) . . . . ?
F2 C01A C3 N2 54.3(4) . . . . ?
F2 C01A C3 C4 -129.0(4) . . . . ?
F3 C01A C3 N2 -63.9(5) . . . . ?
F3 C01A C3 C4 112.8(4) . . . . ?
F4 C1 C9 C8 174.0(3) . . . . ?
F4 C1 C9 C10 -7.8(5) . . . . ?
F4 C1 C9 C8B -126.7(16) . . . . ?
F4 C1 C9 C10B 71(2) . . . . ?
F5 C1 C9 C8 51.3(5) . . . . ?
F5 C1 C9 C10 -130.5(4) . . . . ?
F5 C1 C9 C8B 110.6(16) . . . . ?
F5 C1 C9 C10B -52(2) . . . . ?
F6 C1 C9 C8 -66.3(4) . . . . ?
F6 C1 C9 C10 111.9(4) . . . . ?
F6 C1 C9 C8B -7.1(17) . . . . ?
F6 C1 C9 C10B -169(2) . . . . ?
N1 N2 C3 C01A 171.5(3) . . . . ?
N1 N2 C3 C4 -5.8(3) . . . . ?
N1 C12 C13 C14 -179.6(3) . . . . ?
N1 C12 C17 C16 179.1(3) . . . . ?
N2 N1 C5 O1 174.3(3) . . . . ?
N2 N1 C5 C4 -4.0(3) . . . . ?
N2 N1 C12 C13 -57.9(4) . . . . ?
N2 N1 C12 C17 121.6(3) . . . . ?
N2 C3 C4 C5 3.4(4) . . . . ?
N2 C3 C4 C6 -172.2(3) . . . . ?
C1 C9 C10 C11 -177.8(3) . . . . ?
C1 C9 C8B C7B 179(3) . . . . ?
C1 C9 C10B C11B -176(3) . . . . ?
C01A C3 C4 C5 -173.5(3) . . . . ?
C01A C3 C4 C6 10.9(6) . . . . ?
C01E N2 C3 C01A 31.6(5) . . . . ?
C01E N2 C3 C4 -145.7(3) . . . . ?
C3 C4 C5 O1 -177.7(3) . . . . ?
C3 C4 C5 N1 0.4(3) . . . . ?
C3 C4 C6 C7 -143.5(4) . . . . ?
C3 C4 C6 C11 40.2(5) . . . . ?
C3 C4 C6 C7B 158(2) . . . . ?
C3 C4 C6 C11B -37(2) . . . . ?
C4 C6 C7 C8 -177.1(3) . . . . ?
C4 C6 C11 C10 177.0(3) . . . . ?
C4 C6 C7B C8B 177(3) . . . . ?
C4 C6 C11B C10B -172(3) . . . . ?
C5 N1 N2 C01E 150.6(3) . . . . ?
C5 N1 N2 C3 6.0(3) . . . . ?
C5 N1 C12 C13 100.8(3) . . . . ?
C5 N1 C12 C17 -79.7(4) . . . . ?
C5 C4 C6 C7 41.3(4) . . . . ?
C5 C4 C6 C11 -134.9(3) . . . . ?
C5 C4 C6 C7B -17(2) . . . . ?
C5 C4 C6 C11B 148(2) . . . . ?
C6 C4 C5 O1 -1.4(5) . . . . ?
C6 C4 C5 N1 176.7(3) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C6 C11B C10B C9 -9(7) . . . . ?
C7 C6 C11 C10 0.7(5) . . . . ?
C7 C8 C9 C1 177.9(3) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C8 C9 C10 C11 0.4(5) . . . . ?
C9 C10 C11 C6 -0.6(5) . . . . ?
C9 C8B C7B C6 1(5) . . . . ?
C11 C6 C7 C8 -0.7(5) . . . . ?
C12 N1 N2 C01E -47.7(4) . . . . ?
C12 N1 N2 C3 167.7(3) . . . . ?
C12 N1 C5 O1 13.9(5) . . . . ?
C12 N1 C5 C4 -164.4(3) . . . . ?
C12 C13 C14 C15 -0.6(5) . . . . ?
C13 C12 C17 C16 -1.5(5) . . . . ?
C13 C14 C15 C16 0.8(6) . . . . ?
C14 C15 C16 C17 -1.3(6) . . . . ?
C15 C16 C17 C12 1.6(6) . . . . ?
C17 C12 C13 C14 1.0(5) . . . . ?
F1A C00V C3A N2A -90.2(4) . . . . ?
F1A C00V C3A C4A 93.2(4) . . . . ?
F2A C00V C3A N2A 149.4(3) . . . . ?
F2A C00V C3A C4A -27.2(5) . . . . ?
F3A C00V C3A N2A 30.2(4) . . . . ?
F3A C00V C3A C4A -146.4(3) . . . . ?
N1A N2A C3A C00V 179.5(3) . . . . ?
N1A N2A C3A C4A -3.4(3) . . . . ?
N1A C12A C13A C14A -178.3(3) . . . . ?
N1A C12A C17A C16A 178.0(3) . . . . ?
N2A N1A C5A O002 175.0(3) . . . . ?
N2A N1A C5A C4A -3.2(3) . . . . ?
N2A N1A C12A C13A -29.9(4) . . . . ?
N2A N1A C12A C17A 152.3(3) . . . . ?
N2A C3A C4A C5A 1.5(3) . . . . ?
N2A C3A C4A C6A -178.7(3) . . . . ?
C00V C3A C4A C5A 178.2(3) . . . . ?
C00V C3A C4A C6A -1.9(5) . . . . ?
C1A C9A C10A C11A 180.0(3) . . . . ?
C3A C4A C5A O002 -176.9(3) . . . . ?
C3A C4A C5A N1A 1.1(3) . . . . ?
C3A C4A C6A C7A -42.2(5) . . . . ?
C3A C4A C6A C11A 142.3(3) . . . . ?
C4A C6A C7A C8A -178.4(3) . . . . ?
C4A C6A C11A C10A 176.9(3) . . . . ?
C5A N1A N2A C3A 4.0(3) . . . . ?
C5A N1A N2A C019 139.4(3) . . . . ?
C5A N1A C12A C13A 129.0(3) . . . . ?
C5A N1A C12A C17A -48.7(4) . . . . ?
C5A C4A C6A C7A 137.7(3) . . . . ?
C5A C4A C6A C11A -37.8(4) . . . . ?
C6A C4A C5A O002 3.2(5) . . . . ?
C6A C4A C5A N1A -178.8(2) . . . . ?
C6A C7A C8A C9A 1.9(5) . . . . ?
C7A C6A C11A C10A 1.2(5) . . . . ?
C7A C8A C9A C1A 178.5(3) . . . . ?
C7A C8A C9A C10A 0.6(5) . . . . ?
C8A C9A C10A C11A -2.1(5) . . . . ?
C9A C10A C11A C6A 1.2(5) . . . . ?
C11A C6A C7A C8A -2.8(4) . . . . ?
C12A N1A N2A C3A 166.1(2) . . . . ?
C12A N1A N2A C019 -58.5(3) . . . . ?
C12A N1A C5A O002 14.4(5) . . . . ?
C12A N1A C5A C4A -163.8(3) . . . . ?
C12A C13A C14A C15A 0.0(5) . . . . ?
C13A C12A C17A C16A 0.2(5) . . . . ?
C13A C14A C15A C16A 0.8(5) . . . . ?
C14A C15A C16A C17A -1.1(5) . . . . ?
C15A C16A C17A C12A 0.6(5) . . . . ?
C17A C12A C13A C14A -0.5(5) . . . . ?
C019 N2A C3A C00V 47.8(4) . . . . ?
C019 N2A C3A C4A -135.1(3) . . . . ?
F4A C1A C9A C8A -156.8(11) . . . . ?
F4A C1A C9A C10A 21.1(12) . . . . ?
F5A C1A C9A C8A 95.4(9) . . . . ?
F5A C1A C9A C10A -86.7(9) . . . . ?
F6A C1A C9A C8A -15.8(11) . . . . ?
F6A C1A C9A C10A 162.1(10) . . . . ?
F4B C1A C9A C8A -94.7(5) . . . . ?
F4B C1A C9A C10A 83.2(6) . . . . ?
F5B C1A C9A C8A 18.2(9) . . . . ?
F5B C1A C9A C10A -163.9(8) . . . . ?
F6B C1A C9A C8A 149.3(8) . . . . ?
F6B C1A C9A C10A -32.8(9) . . . . ?
C8B C9 C10B C11B 22(5) . . . . ?
C7B C6 C11B C10B -8(6) . . . . ?
C11B C6 C7B C8B 11(5) . . . . ?
C10B C9 C8B C7B -18(5) . . . . ?
