#------------------------------------------------------------------------------
#$Date: 2024-04-05 03:12:28 +0300 (Fri, 05 Apr 2024) $
#$Revision: 291052 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159812.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_7159812
loop_
_publ_author_name
'Chen, Feijing'
'Zhao, Xiao-Xiao'
'Zhang, Hao-Tian'
'Ma, Yan-Na'
'Chen, Xuenian'
_publ_section_title
;
 Facile Friedel-Crafts alkylation of arenes under solvent-free conditions.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2187
_journal_page_last               2191
_journal_paper_doi               10.1039/d4ob00162a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C17 H12 F3 N O2'
_chemical_formula_sum            'C17 H12 F3 N O2'
_chemical_formula_weight         319.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-12-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-01-29 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.316(8)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   34.085(2)
_cell_length_b                   11.9376(5)
_cell_length_c                   15.8740(12)
_cell_measurement_reflns_used    2764
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.1600
_cell_measurement_theta_min      3.9460
_cell_volume                     5975.3(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -45.00   1.00    3.50    --  -33.50 178.00  90.00   62
  2  ω    -55.00  26.00   1.00    3.50    --  -33.50  37.00 150.00   81
  3  ω    -64.00 -22.00   1.00    3.50    --  -33.50 -19.00-180.00   42
  4  ω   -108.00 -74.00   1.00    3.50    --  -33.50 178.00   0.00   34
  5  ω    -55.00  23.00   1.00    3.50    --  -33.50  19.00  60.00   78
  6  ω     84.00 110.00   1.00    3.50    --   36.47 178.00 -90.00   26
  7  ω     62.00 146.00   1.00   17.50    --  108.00 178.00  60.00   84
  8  ω    102.00 161.00   1.00   17.50    --  108.00  77.00 -30.00   59
  9  ω     78.00 104.00   1.00   17.50    --  108.00-111.00-180.00   26
 10  ω    106.00 164.00   1.00   17.50    --  108.00  45.00  90.00   58
 11  ω     94.00 173.00   1.00   17.50    --  108.00  61.00-150.00   79
 12  ω     40.00 126.00   1.00   17.50    --  108.00 -61.00 120.00   86
 13  ω     48.00 109.00   1.00   17.50    --  108.00-111.00  90.00   61
 14  ω     94.00 176.00   1.00   17.50    --  108.00  61.00 -90.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0043732072
_diffrn_orient_matrix_UB_12      0.1049318681
_diffrn_orient_matrix_UB_13      -0.0593686737
_diffrn_orient_matrix_UB_21      -0.0324059550
_diffrn_orient_matrix_UB_22      -0.0618900818
_diffrn_orient_matrix_UB_23      -0.0822184017
_diffrn_orient_matrix_UB_31      -0.0363056536
_diffrn_orient_matrix_UB_32      0.0427322563
_diffrn_orient_matrix_UB_33      0.0268110799
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11015
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.960
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.021
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.420
_exptl_crystal_description       cube
_exptl_crystal_F_000             2624
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5333
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0739
_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)+(0.1105P)²+1.0053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1964
_refine_ls_wR_factor_ref         0.2384
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3297
_reflns_number_total             5333
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00162a2.cif
_cod_data_source_block           202312335
_cod_depositor_comments          'Adding full bibliography for 7159812.cif.'
_cod_database_code               7159812
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C17H20N3O1
_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   0.932
_shelx_estimated_absorpt_t_min   0.854
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
 F2-F3 \\sim F2-F1 \\sim F3-F1 \\sim F2A-F3A \\sim F2A-F1A
 with sigma of 0.04
 C16-F2 \\sim C16-F3 \\sim C16-F1 \\sim C16-F2A \\sim C16-F3A \\sim C16-F1A
 with sigma of 0.02
 F1'-F3' \\sim F1'-F2' \\sim F3'-F2' \\sim F1'A-F3'A \\sim F1'A-F2'A \\sim
F3'A-F2'A
 with sigma of 0.04
 C16'-F1' \\sim C16'-F3' \\sim C16'-F2' \\sim C16'-F1'A \\sim C16'-F3'A \\sim
C16'-F2'A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F1'A) \\sim Ueq, Uanis(F1') \\sim Ueq, Uanis(F3'A) \\sim Ueq, Uanis(F3')
\\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F3A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2) = Uanis(F2A)
Uanis(F3) = Uanis(F3A)
Uanis(F1) = Uanis(F1A)
Uanis(F1') = Uanis(F1'A)
Uanis(F3') = Uanis(F3'A)
Uanis(F2') = Uanis(F2'A)
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(F1'A)=Sof(F2'A)=Sof(F3'A)=1-FVAR(2)
 Sof(F1')=Sof(F2')=Sof(F3')=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14),
 C15(H15), C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5'), C11'(H11'),
 C13'(H13'), C14'(H14'), C15'(H15')
5.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C17'(H17D,H17E,H17F)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.798
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.32883(9) 0.5489(3) 0.0160(3) 0.1205(14) Uani 0.904(6) 1 d D . P A 1
F1A F 0.3626(12) 0.564(3) -0.0171(14) 0.1205(14) Uani 0.096(6) 1 d D . P A 2
F2 F 0.3770(2) 0.5907(3) 0.1392(3) 0.169(2) Uani 0.904(6) 1 d D U P A 1
F2A F 0.3364(8) 0.567(3) 0.083(3) 0.169(2) Uani 0.096(6) 1 d D U P A 2
F3 F 0.38930(14) 0.5851(3) 0.0187(3) 0.1318(14) Uani 0.904(6) 1 d D . P A 1
F3A F 0.3989(8) 0.590(3) 0.1315(19) 0.1318(14) Uani 0.096(6) 1 d D U P A 2
O1 O 0.30361(7) 0.0090(2) 0.17581(16) 0.0730(6) Uani 1 1 d . . . . .
O2 O 0.36859(8) -0.0308(2) 0.1675(2) 0.0850(7) Uani 1 1 d . . . . .
N1 N 0.29711(9) 0.1915(2) 0.1456(2) 0.0715(7) Uani 1 1 d . . . . .
C1 C 0.21135(13) 0.1844(4) 0.1502(3) 0.0905(11) Uani 1 1 d . . . . .
H1 H 0.2191 0.2502 0.1292 0.109 Uiso 1 1 calc R . . . .
C2 C 0.17225(15) 0.1769(5) 0.1577(4) 0.1132(16) Uani 1 1 d . . . . .
H2 H 0.1535 0.2369 0.1403 0.136 Uiso 1 1 calc R . . . .
C3 C 0.16127(17) 0.0809(6) 0.1906(4) 0.121(2) Uani 1 1 d . . . . .
H3 H 0.1352 0.0761 0.1963 0.146 Uiso 1 1 calc R . . . .
C4 C 0.18858(17) -0.0077(5) 0.2149(3) 0.1085(16) Uani 1 1 d . . . . .
H4 H 0.1810 -0.0725 0.2375 0.130 Uiso 1 1 calc R . . . .
C5 C 0.22719(14) -0.0022(4) 0.2064(3) 0.0861(11) Uani 1 1 d . . . . .
H5 H 0.2454 -0.0634 0.2225 0.103 Uiso 1 1 calc R . . . .
C6 C 0.23884(11) 0.0947(3) 0.1737(2) 0.0743(9) Uani 1 1 d . . . . .
C7 C 0.27918(11) 0.1044(3) 0.1640(2) 0.0693(8) Uani 1 1 d . . . . .
C8 C 0.33854(11) 0.0431(3) 0.1616(2) 0.0683(8) Uani 1 1 d . . . . .
C9 C 0.33546(11) 0.1544(3) 0.1434(2) 0.0695(8) Uani 1 1 d . . . . .
C10 C 0.36415(11) 0.2288(3) 0.1211(3) 0.0715(8) Uani 1 1 d . . . . .
C11 C 0.35397(10) 0.3414(3) 0.1029(2) 0.0670(8) Uani 1 1 d . . . . .
H11 H 0.3287 0.3688 0.1044 0.080 Uiso 1 1 calc R . . . .
C12 C 0.38089(11) 0.4125(3) 0.0826(3) 0.0723(8) Uani 1 1 d . . . . .
C13 C 0.41792(14) 0.3755(4) 0.0794(4) 0.1014(14) Uani 1 1 d . . . . .
H13 H 0.4360 0.4244 0.0661 0.122 Uiso 1 1 calc R . . . .
C14 C 0.42818(17) 0.2638(4) 0.0964(5) 0.135(2) Uani 1 1 d . . . . .
H14 H 0.4533 0.2371 0.0939 0.162 Uiso 1 1 calc R . . . .
C15 C 0.40183(15) 0.1919(4) 0.1168(4) 0.1142(18) Uani 1 1 d . . . . .
H15 H 0.4094 0.1169 0.1280 0.137 Uiso 1 1 calc R . . . .
C16 C 0.36962(13) 0.5334(3) 0.0650(3) 0.0824(10) Uani 1 1 d D . . . .
C17 C 0.35894(15) -0.1467(3) 0.1684(3) 0.0963(12) Uani 1 1 d . . . . .
H17A H 0.3360 -0.1659 0.1127 0.144 Uiso 1 1 calc GR . . . .
H17B H 0.3508 -0.1619 0.2190 0.144 Uiso 1 1 calc GR . . . .
H17C H 0.3835 -0.1904 0.1743 0.144 Uiso 1 1 calc GR . . . .
F1' F 0.51294(15) 0.5789(4) 0.3925(6) 0.154(2) Uani 0.688(4) 1 d D U P B 1
F1'A F 0.5043(3) 0.5882(9) 0.4505(9) 0.154(2) Uani 0.312(4) 1 d D U P B 2
F2' F 0.44958(19) 0.6103(4) 0.3010(4) 0.1417(19) Uani 0.688(4) 1 d D . P B 1
F2'A F 0.4866(4) 0.5883(8) 0.3117(8) 0.1417(19) Uani 0.312(4) 1 d D . P B 2
F3' F 0.4644(2) 0.6132(4) 0.4393(5) 0.143(2) Uani 0.688(4) 1 d D U P B 1
F3'A F 0.4428(4) 0.6122(10) 0.3700(10) 0.143(2) Uani 0.312(4) 1 d D U P B 2
O1' O 0.39460(8) 1.1803(2) 0.38746(18) 0.0776(6) Uani 1 1 d . . . . .
O2' O 0.45765(10) 1.2191(2) 0.3701(3) 0.1039(10) Uani 1 1 d . . . . .
N1' N 0.39657(9) 0.9944(2) 0.39772(19) 0.0685(7) Uani 1 1 d . . . . .
C1' C 0.31673(12) 1.0001(3) 0.4314(3) 0.0778(9) Uani 1 1 d . . . . .
H1' H 0.3303 0.9311 0.4391 0.093 Uiso 1 1 calc R . . . .
C2' C 0.27882(12) 1.0087(4) 0.4417(3) 0.0875(11) Uani 1 1 d . . . . .
H2' H 0.2667 0.9453 0.4560 0.105 Uiso 1 1 calc R . . . .
C3' C 0.25829(13) 1.1105(4) 0.4311(3) 0.0962(13) Uani 1 1 d . . . . .
H3' H 0.2324 1.1158 0.4380 0.115 Uiso 1 1 calc R . . . .
C4' C 0.27635(14) 1.2037(4) 0.4104(3) 0.0922(11) Uani 1 1 d . . . . .
H4' H 0.2627 1.2725 0.4038 0.111 Uiso 1 1 calc R . . . .
C5' C 0.31430(13) 1.1966(3) 0.3993(3) 0.0808(10) Uani 1 1 d . . . . .
H5' H 0.3262 1.2602 0.3848 0.097 Uiso 1 1 calc R . . . .
C6' C 0.33496(11) 1.0933(3) 0.4098(2) 0.0685(8) Uani 1 1 d . . . . .
C7' C 0.37529(11) 1.0833(3) 0.3989(2) 0.0681(8) Uani 1 1 d . . . . .
C8' C 0.43076(11) 1.1442(3) 0.3788(3) 0.0738(9) Uani 1 1 d . . . . .
C9' C 0.43296(10) 1.0312(3) 0.3851(2) 0.0669(8) Uani 1 1 d . . . . .
C10' C 0.46525(10) 0.9534(3) 0.3805(2) 0.0682(8) Uani 1 1 d . . . . .
C11' C 0.45865(10) 0.8397(3) 0.3822(2) 0.0662(8) Uani 1 1 d . . . . .
H11' H 0.4338 0.8133 0.3863 0.079 Uiso 1 1 calc R . . . .
C12' C 0.48864(11) 0.7647(3) 0.3777(2) 0.0700(8) Uani 1 1 d . . . . .
C13' C 0.52593(12) 0.8006(3) 0.3729(3) 0.0811(10) Uani 1 1 d . . . . .
H13' H 0.5462 0.7496 0.3708 0.097 Uiso 1 1 calc R . . . .
C14' C 0.53263(13) 0.9143(4) 0.3711(4) 0.0981(14) Uani 1 1 d . . . . .
H14' H 0.5576 0.9404 0.3674 0.118 Uiso 1 1 calc R . . . .
C15' C 0.50288(13) 0.9893(3) 0.3749(3) 0.0900(11) Uani 1 1 d . . . . .
H15' H 0.5080 1.0656 0.3737 0.108 Uiso 1 1 calc R . . . .
C16' C 0.48005(12) 0.6427(3) 0.3777(3) 0.0849(11) Uani 1 1 d D . . . .
C17' C 0.44319(16) 1.3317(3) 0.3484(4) 0.1080(15) Uani 1 1 d . . . . .
H17D H 0.4178 1.3323 0.2943 0.162 Uiso 1 1 calc GR . . . .
H17E H 0.4647 1.3752 0.3384 0.162 Uiso 1 1 calc GR . . . .
H17F H 0.4373 1.3634 0.3980 0.162 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C8 O1 C7 104.6(3) . . ?
C8 O2 C17 118.1(3) . . ?
C7 N1 C9 106.1(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C6 C1 C2 120.2(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(6) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(5) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(5) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.2(4) . . ?
C1 C6 C7 119.0(4) . . ?
C5 C6 C7 121.8(4) . . ?
O1 C7 C6 117.9(3) . . ?
N1 C7 O1 112.4(3) . . ?
N1 C7 C6 129.7(3) . . ?
O2 C8 O1 119.4(3) . . ?
O2 C8 C9 131.4(3) . . ?
C9 C8 O1 109.2(3) . . ?
N1 C9 C10 122.2(3) . . ?
C8 C9 N1 107.7(3) . . ?
C8 C9 C10 130.0(3) . . ?
C11 C10 C9 120.1(3) . . ?
C15 C10 C9 122.5(3) . . ?
C15 C10 C11 117.4(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C16 119.6(3) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 C16 119.1(3) . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.6(4) . . ?
C14 C13 H13 120.7 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.2(4) . . ?
C14 C15 H15 119.4 . . ?
F1 C16 C12 112.6(3) . . ?
F1A C16 F2A 106.5(17) . . ?
F1A C16 F3A 117(2) . . ?
F1A C16 C12 113.4(15) . . ?
F2 C16 F1 105.0(4) . . ?
F2 C16 F3 107.1(4) . . ?
F2 C16 C12 113.1(4) . . ?
F2A C16 F3A 96.9(16) . . ?
F2A C16 C12 115.6(15) . . ?
F3 C16 F1 104.4(4) . . ?
F3 C16 C12 113.9(3) . . ?
F3A C16 C12 106.5(18) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8' O1' C7' 104.1(3) . . ?
C8' O2' C17' 118.1(3) . . ?
C7' N1' C9' 106.1(3) . . ?
C2' C1' H1' 119.8 . . ?
C2' C1' C6' 120.3(4) . . ?
C6' C1' H1' 119.8 . . ?
C1' C2' H2' 119.7 . . ?
C1' C2' C3' 120.7(4) . . ?
C3' C2' H2' 119.7 . . ?
C2' C3' H3' 120.3 . . ?
C4' C3' C2' 119.4(4) . . ?
C4' C3' H3' 120.3 . . ?
C3' C4' H4' 119.6 . . ?
C3' C4' C5' 120.8(4) . . ?
C5' C4' H4' 119.6 . . ?
C4' C5' H5' 120.2 . . ?
C4' C5' C6' 119.6(4) . . ?
C6' C5' H5' 120.2 . . ?
C1' C6' C5' 119.2(3) . . ?
C1' C6' C7' 119.9(3) . . ?
C5' C6' C7' 120.9(3) . . ?
O1' C7' C6' 117.9(3) . . ?
N1' C7' O1' 113.0(3) . . ?
N1' C7' C6' 129.2(3) . . ?
O2' C8' O1' 119.1(3) . . ?
O2' C8' C9' 131.2(3) . . ?
C9' C8' O1' 109.6(3) . . ?
N1' C9' C10' 122.1(3) . . ?
C8' C9' N1' 107.2(3) . . ?
C8' C9' C10' 130.7(3) . . ?
C11' C10' C9' 119.5(3) . . ?
C11' C10' C15' 117.9(3) . . ?
C15' C10' C9' 122.6(3) . . ?
C10' C11' H11' 119.7 . . ?
C10' C11' C12' 120.6(3) . . ?
C12' C11' H11' 119.7 . . ?
C11' C12' C16' 119.1(3) . . ?
C13' C12' C11' 121.3(3) . . ?
C13' C12' C16' 119.6(3) . . ?
C12' C13' H13' 120.9 . . ?
C12' C13' C14' 118.3(3) . . ?
C14' C13' H13' 120.9 . . ?
C13' C14' H14' 119.6 . . ?
C15' C14' C13' 120.7(3) . . ?
C15' C14' H14' 119.6 . . ?
C10' C15' H15' 119.4 . . ?
C14' C15' C10' 121.2(4) . . ?
C14' C15' H15' 119.4 . . ?
F1' C16' F2' 108.4(5) . . ?
F1' C16' F3' 105.8(5) . . ?
F1' C16' C12' 114.7(4) . . ?
F1'A C16' F2'A 102.4(8) . . ?
F1'A C16' C12' 115.4(6) . . ?
F2' C16' F3' 101.8(5) . . ?
F2' C16' C12' 111.9(4) . . ?
F2'A C16' C12' 112.9(5) . . ?
F3' C16' C12' 113.3(4) . . ?
F3'A C16' F1'A 102.4(8) . . ?
F3'A C16' F2'A 104.1(8) . . ?
F3'A C16' C12' 117.8(6) . . ?
O2' C17' H17D 109.5 . . ?
O2' C17' H17E 109.5 . . ?
O2' C17' H17F 109.5 . . ?
H17D C17' H17E 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
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 C16 1.323(5) . ?
F1A C16 1.286(15) . ?
F2 C16 1.300(5) . ?
F2A C16 1.328(14) . ?
F3 C16 1.322(5) . ?
F3A C16 1.331(16) . ?
O1 C7 1.381(4) . ?
O1 C8 1.356(4) . ?
O2 C8 1.328(4) . ?
O2 C17 1.423(5) . ?
N1 C7 1.295(4) . ?
N1 C9 1.393(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(6) . ?
C1 C6 1.378(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.364(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(6) . ?
C6 C7 1.445(5) . ?
C8 C9 1.355(5) . ?
C9 C10 1.460(5) . ?
C10 C11 1.391(5) . ?
C10 C15 1.384(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(5) . ?
C12 C13 1.356(5) . ?
C12 C16 1.492(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.367(6) . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
F1' C16' 1.301(5) . ?
F1'A C16' 1.310(11) . ?
F2' C16' 1.324(6) . ?
F2'A C16' 1.321(10) . ?
F3' C16' 1.327(6) . ?
F3'A C16' 1.282(11) . ?
O1' C7' 1.378(4) . ?
O1' C8' 1.361(4) . ?
O2' C8' 1.325(4) . ?
O2' C17' 1.429(5) . ?
N1' C7' 1.289(4) . ?
N1' C9' 1.400(4) . ?
C1' H1' 0.9300 . ?
C1' C2' 1.366(5) . ?
C1' C6' 1.379(5) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.381(6) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.370(6) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.373(5) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.399(5) . ?
C6' C7' 1.454(5) . ?
C8' C9' 1.353(5) . ?
C9' C10' 1.463(5) . ?
C10' C11' 1.377(5) . ?
C10' C15' 1.387(5) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.381(5) . ?
C12' C13' 1.371(5) . ?
C12' C16' 1.485(5) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.378(6) . ?
C14' H14' 0.9300 . ?
C14' C15' 1.371(6) . ?
C15' H15' 0.9300 . ?
C17' H17D 0.9600 . ?
C17' H17E 0.9600 . ?
C17' H17F 0.9600 . ?
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
O1 C8 C9 N1 -0.4(4) . . . . ?
O1 C8 C9 C10 -178.1(3) . . . . ?
O2 C8 C9 N1 -180.0(4) . . . . ?
O2 C8 C9 C10 2.3(7) . . . . ?
N1 C9 C10 C11 1.2(5) . . . . ?
N1 C9 C10 C15 -178.5(4) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C1 C6 C7 O1 -171.2(3) . . . . ?
C1 C6 C7 N1 9.2(6) . . . . ?
C2 C1 C6 C5 -1.1(6) . . . . ?
C2 C1 C6 C7 179.1(4) . . . . ?
C2 C3 C4 C5 -0.3(8) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C4 C5 C6 C7 179.7(4) . . . . ?
C5 C6 C7 O1 9.0(5) . . . . ?
C5 C6 C7 N1 -170.6(4) . . . . ?
C6 C1 C2 C3 1.5(7) . . . . ?
C7 O1 C8 O2 -179.5(3) . . . . ?
C7 O1 C8 C9 0.8(4) . . . . ?
C7 N1 C9 C8 -0.2(4) . . . . ?
C7 N1 C9 C10 177.7(3) . . . . ?
C8 O1 C7 N1 -1.0(4) . . . . ?
C8 O1 C7 C6 179.2(3) . . . . ?
C8 C9 C10 C11 178.6(4) . . . . ?
C8 C9 C10 C15 -1.1(7) . . . . ?
C9 N1 C7 O1 0.8(4) . . . . ?
C9 N1 C7 C6 -179.5(3) . . . . ?
C9 C10 C11 C12 179.5(3) . . . . ?
C9 C10 C15 C14 -179.5(5) . . . . ?
C10 C11 C12 C13 0.2(6) . . . . ?
C10 C11 C12 C16 -178.8(4) . . . . ?
C11 C10 C15 C14 0.8(8) . . . . ?
C11 C12 C13 C14 0.5(8) . . . . ?
C11 C12 C16 F1 -40.6(5) . . . . ?
C11 C12 C16 F1A -114.7(19) . . . . ?
C11 C12 C16 F2 78.2(6) . . . . ?
C11 C12 C16 F2A 8.8(18) . . . . ?
C11 C12 C16 F3 -159.2(4) . . . . ?
C11 C12 C16 F3A 115.2(15) . . . . ?
C12 C13 C14 C15 -0.6(11) . . . . ?
C13 C12 C16 F1 140.4(4) . . . . ?
C13 C12 C16 F1A 66(2) . . . . ?
C13 C12 C16 F2 -100.8(6) . . . . ?
C13 C12 C16 F2A -170.2(18) . . . . ?
C13 C12 C16 F3 21.8(6) . . . . ?
C13 C12 C16 F3A -63.8(15) . . . . ?
C13 C14 C15 C10 -0.1(11) . . . . ?
C15 C10 C11 C12 -0.8(6) . . . . ?
C16 C12 C13 C14 179.5(5) . . . . ?
C17 O2 C8 O1 13.7(5) . . . . ?
C17 O2 C8 C9 -166.7(4) . . . . ?
O1' C8' C9' N1' 0.3(4) . . . . ?
O1' C8' C9' C10' -179.7(3) . . . . ?
O2' C8' C9' N1' 177.2(4) . . . . ?
O2' C8' C9' C10' -2.8(8) . . . . ?
N1' C9' C10' C11' 4.7(5) . . . . ?
N1' C9' C10' C15' -175.0(3) . . . . ?
C1' C2' C3' C4' -0.2(7) . . . . ?
C1' C6' C7' O1' -172.9(3) . . . . ?
C1' C6' C7' N1' 7.6(6) . . . . ?
C2' C1' C6' C5' 0.5(6) . . . . ?
C2' C1' C6' C7' -179.9(3) . . . . ?
C2' C3' C4' C5' 0.6(7) . . . . ?
C3' C4' C5' C6' -0.5(6) . . . . ?
C4' C5' C6' C1' -0.1(6) . . . . ?
C4' C5' C6' C7' -179.7(3) . . . . ?
C5' C6' C7' O1' 6.7(5) . . . . ?
C5' C6' C7' N1' -172.9(4) . . . . ?
C6' C1' C2' C3' -0.3(6) . . . . ?
C7' O1' C8' O2' -177.5(3) . . . . ?
C7' O1' C8' C9' -0.1(4) . . . . ?
C7' N1' C9' C8' -0.3(4) . . . . ?
C7' N1' C9' C10' 179.7(3) . . . . ?
C8' O1' C7' N1' -0.1(4) . . . . ?
C8' O1' C7' C6' -179.7(3) . . . . ?
C8' C9' C10' C11' -175.3(4) . . . . ?
C8' C9' C10' C15' 5.0(6) . . . . ?
C9' N1' C7' O1' 0.2(4) . . . . ?
C9' N1' C7' C6' 179.8(3) . . . . ?
C9' C10' C11' C12' 179.8(3) . . . . ?
C9' C10' C15' C14' 179.7(4) . . . . ?
C10' C11' C12' C13' 1.0(6) . . . . ?
C10' C11' C12' C16' -178.8(4) . . . . ?
C11' C10' C15' C14' 0.0(7) . . . . ?
C11' C12' C13' C14' -1.0(6) . . . . ?
C11' C12' C16' F1' -166.3(5) . . . . ?
C11' C12' C16' F1'A -112.4(7) . . . . ?
C11' C12' C16' F2' 69.7(5) . . . . ?
C11' C12' C16' F2'A 130.3(7) . . . . ?
C11' C12' C16' F3' -44.7(6) . . . . ?
C11' C12' C16' F3'A 8.9(9) . . . . ?
C12' C13' C14' C15' 0.5(7) . . . . ?
C13' C12' C16' F1' 13.9(7) . . . . ?
C13' C12' C16' F1'A 67.9(8) . . . . ?
C13' C12' C16' F2' -110.0(5) . . . . ?
C13' C12' C16' F2'A -49.4(9) . . . . ?
C13' C12' C16' F3' 135.6(5) . . . . ?
C13' C12' C16' F3'A -170.8(8) . . . . ?
C13' C14' C15' C10' 0.0(8) . . . . ?
C15' C10' C11' C12' -0.4(5) . . . . ?
C16' C12' C13' C14' 178.7(4) . . . . ?
C17' O2' C8' O1' -14.6(6) . . . . ?
C17' O2' C8' C9' 168.7(5) . . . . ?
