#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:57:47 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225243 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/67/7156777.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_7156777
loop_
_publ_author_name
'Guo, Jia'
'Xu, Cong'
'Wang, Ling'
'Huang, Wanqiao'
'Wang, Mang'
_publ_section_title
;
Catalyst-free and selective trifluoromethylative cyclization of
acryloanilides using PhICF3Cl.
;
_journal_issue 18
_journal_name_full 'Organic & biomolecular chemistry'
_journal_page_first 4593
_journal_page_last 4599
_journal_paper_doi 10.1039/c9ob00601j
_journal_volume 17
_journal_year 2019
_chemical_formula_moiety '0.21(C20 H18 F3 N O)'
_chemical_formula_sum 'C4.21 H3.79 F0.63 N0.21 O0.21'
_chemical_formula_weight 72.71
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_Hall '-P 2yn'
_space_group_name_H-M_alt 'P 1 21/n 1'
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 1 21/n 1'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary dual
_audit_block_doi 10.5517/ccdc.csd.cc207z9k
_audit_creation_date 2018-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-07-09 deposited with the CCDC. 2019-04-08 downloaded from the CCDC.
;
_cell_angle_alpha 90
_cell_angle_beta 106.736(6)
_cell_angle_gamma 90
_cell_formula_units_Z 19
_cell_length_a 8.1844(9)
_cell_length_b 24.475(3)
_cell_length_c 8.6835(9)
_cell_measurement_reflns_used 6162
_cell_measurement_temperature 294(2)
_cell_measurement_theta_max 72.11
_cell_measurement_theta_min 3.61
_cell_volume 1665.7(3)
_computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction 'SAINT v8.37A (Bruker, 2015)'
_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 'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature 294.21
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0302
_diffrn_reflns_av_unetI/netI 0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 30
_diffrn_reflns_limit_k_min -29
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_number 12352
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full 67.679
_diffrn_reflns_theta_max 72.302
_diffrn_reflns_theta_min 3.612
_exptl_absorpt_coefficient_mu 0.908
_exptl_absorpt_correction_type none
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.377
_exptl_crystal_description block
_exptl_crystal_F_000 720
_exptl_crystal_size_max 0.4
_exptl_crystal_size_mid 0.3
_exptl_crystal_size_min 0.2
_refine_diff_density_max 0.226
_refine_diff_density_min -0.256
_refine_diff_density_rms 0.037
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.050
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 298
_refine_ls_number_reflns 3252
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.050
_refine_ls_R_factor_all 0.0664
_refine_ls_R_factor_gt 0.0520
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.7873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1199
_refine_ls_wR_factor_ref 0.1280
_reflns_Friedel_coverage 0.000
_reflns_number_gt 2586
_reflns_number_total 3252
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file c9ob00601j2.cif
_cod_data_source_block a
_cod_depositor_comments 'Adding full bibliography for 7156777.cif.'
_cod_database_code 7156777
_shelx_shelxl_version_number 2014/7
_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.
;
_olex2_refinement_description
;
;
_shelx_res_file
;
a.res created by SHELXL-2014/7
TITL a_a.res in P2(1)/n
REM Old TITL a in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.197, Rweak 0.021, Alpha 0.048, Orientation as input
REM Formula found by SHELXT: C19 N2 O F3
CELL 1.54178 8.1844 24.4751 8.6835 90 106.736 90
ZERR 19 0.0009 0.0029 0.0009 0 0.006 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H F N O
UNIT 80 72 12 4 4
L.S. 10
PLAN 20
TEMP 21.06
BOND $H
LIST 6
fmap 2
acta
REM
REM
REM
WGHT 0.050200 0.787300
FVAR 1.01586
F1 3 1.011111 0.551762 0.905582 11.00000 0.06582 0.12173 =
0.06064 0.02230 0.00467 0.01184
O1 5 0.765665 0.623398 1.072742 11.00000 0.08745 0.07095 =
0.03790 0.00592 0.02611 -0.00504
F3 3 1.120915 0.601063 0.766742 11.00000 0.04346 0.10543 =
0.12344 0.02858 0.00476 -0.00730
N1 4 0.863966 0.680672 0.916965 11.00000 0.05688 0.04322 =
0.03097 -0.00630 0.01090 -0.00681
F2 3 1.111420 0.515038 0.731623 11.00000 0.09355 0.12179 =
0.13291 -0.02489 0.00157 0.07304
C15 1 0.815259 0.664446 0.629305 11.00000 0.03251 0.03453 =
0.03254 -0.00223 0.00974 0.00013
C16 1 0.872208 0.698306 0.764296 11.00000 0.03985 0.03732 =
0.03581 -0.00323 0.01118 -0.00423
C10 1 0.734077 0.608896 0.640752 11.00000 0.03643 0.02937 =
0.03175 -0.00219 0.00868 0.00059
C5 1 0.568543 0.604919 0.501504 11.00000 0.04227 0.02932 =
0.04018 -0.00110 0.00493 -0.00355
C20 1 0.834166 0.682904 0.484237 11.00000 0.05293 0.04691 =
0.03720 -0.00465 0.01864 -0.00640
C13 1 0.769842 0.636920 0.938477 11.00000 0.04979 0.04353 =
0.03392 0.00241 0.01565 0.00565
C11 1 0.854019 0.561305 0.630434 11.00000 0.04980 0.04082 =
0.04677 -0.00331 0.01443 0.00844
C8 1 0.660405 0.608596 0.788458 11.00000 0.04045 0.03476 =
0.04041 0.00363 0.01606 -0.00002
C6 1 0.432360 0.624639 0.550651 11.00000 0.03944 0.03626 =
0.05536 0.00392 0.00849 -0.00184
C7 1 0.492969 0.641987 0.722897 11.00000 0.04072 0.04634 =
0.05452 0.00188 0.02074 0.00333
C9 1 0.614102 0.551422 0.832437 11.00000 0.06213 0.04178 =
0.06318 0.00873 0.02310 -0.00684
C4 1 0.543937 0.586642 0.345117 11.00000 0.06086 0.03819 =
0.04538 -0.00788 0.00364 -0.00315
C17 1 0.941494 0.749353 0.748997 11.00000 0.06159 0.04640 =
0.05199 -0.01262 0.01812 -0.01773
C19 1 0.905551 0.733082 0.471216 11.00000 0.07864 0.05656 =
0.05046 0.00577 0.03309 -0.01387
C18 1 0.957815 0.766390 0.603272 11.00000 0.07749 0.04653 =
0.06663 -0.00097 0.03142 -0.02257
C12 1 1.021785 0.557348 0.756666 11.00000 0.04715 0.05910 =
0.06455 0.00460 0.01525 0.01529
C2 1 0.268945 0.625722 0.443343 11.00000 0.04201 0.05806 =
0.07807 0.00890 0.00311 0.00188
C3 1 0.379838 0.587963 0.238887 11.00000 0.07862 0.04794 =
0.04928 -0.00529 -0.01085 -0.00657
C1 1 0.244750 0.606661 0.288259 11.00000 0.05850 0.05861 =
0.07584 0.00486 -0.02032 -0.00841
C14 1 0.951782 0.712788 1.058920 11.00000 0.09680 0.06092 =
0.03657 -0.01186 0.00718 -0.01277
H9A 2 0.541585 0.533076 0.735866 11.00000 0.06241
H9B 2 0.548288 0.554339 0.912335 11.00000 0.09510
H9C 2 0.715015 0.527898 0.875167 11.00000 0.06609
H14A 2 0.947634 0.690535 1.152533 11.00000 0.08333
H14B 2 1.075031 0.717397 1.061304 11.00000 0.08604
H14C 2 0.893308 0.748639 1.057139 11.00000 0.09069
H7A 2 0.521588 0.684129 0.730889 11.00000 0.05079
H7B 2 0.419306 0.634637 0.784841 11.00000 0.06065
H20 2 0.794147 0.659839 0.389279 11.00000 0.05688
H4 2 0.643717 0.571686 0.308255 11.00000 0.05884
H17 2 0.974769 0.773107 0.840104 11.00000 0.06599
H1 2 0.129878 0.605622 0.210517 11.00000 0.09196
H3 2 0.358463 0.573098 0.124183 11.00000 0.07994
H19 2 0.914256 0.744532 0.371544 11.00000 0.08125
H2 2 0.175918 0.637560 0.482805 11.00000 0.07352
H18 2 1.005700 0.802154 0.593571 11.00000 0.07797
H11A 2 0.881606 0.564822 0.531240 11.00000 0.05016
H11B 2 0.795202 0.525232 0.627245 11.00000 0.06237
HKLF 4
REM a_a.res in P2(1)/n
REM R1 = 0.0520 for 2586 Fo > 4sig(Fo) and 0.0664 for all 3252 data
REM 298 parameters refined using 0 restraints
END
WGHT 0.0502 0.7873
REM Highest difference peak 0.226, deepest hole -0.256, 1-sigma level 0.037
Q1 1 0.7088 0.6089 0.7253 11.00000 0.05 0.23
Q2 1 1.0291 0.5165 0.8391 11.00000 0.05 0.22
Q3 1 0.5770 0.6229 0.7554 11.00000 0.05 0.21
Q4 1 0.6561 0.6069 0.5605 11.00000 0.05 0.20
Q5 1 1.1222 0.5681 0.6807 11.00000 0.05 0.19
Q6 1 1.0356 0.5852 0.8572 11.00000 0.05 0.18
Q7 1 0.7147 0.6223 0.8574 11.00000 0.05 0.17
Q8 1 0.4976 0.6097 0.5366 11.00000 0.05 0.15
Q9 1 0.6303 0.5831 0.8078 11.00000 0.05 0.14
Q10 1 0.8043 0.5894 0.6459 11.00000 0.05 0.14
Q11 1 0.5334 0.5779 0.4465 11.00000 0.05 0.13
Q12 1 0.8310 0.6097 1.0221 11.00000 0.05 0.13
Q13 1 0.8410 0.6910 0.8357 11.00000 0.05 0.13
Q14 1 0.4459 0.6393 0.6205 11.00000 0.05 0.12
Q15 1 0.7844 0.6342 0.6396 11.00000 0.05 0.12
Q16 1 0.5634 0.6036 0.4405 11.00000 0.05 0.12
Q17 1 0.8388 0.5348 0.5289 11.00000 0.05 0.12
Q18 1 0.8553 0.6770 0.7023 11.00000 0.05 0.12
Q19 1 0.3953 0.6481 0.4920 11.00000 0.05 0.11
Q20 1 1.2123 0.4675 0.7413 11.00000 0.05 0.11
;
_shelx_res_checksum 3034
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
F1 F 1.0111(2) 0.55176(8) 0.90558(18) 0.0856(5) Uani 1 1 d
O1 O 0.7657(2) 0.62340(7) 1.07274(18) 0.0637(5) Uani 1 1 d
F3 F 1.12092(19) 0.60106(8) 0.7667(2) 0.0948(6) Uani 1 1 d
N1 N 0.8640(2) 0.68067(7) 0.91697(18) 0.0441(4) Uani 1 1 d
F2 F 1.1114(3) 0.51504(9) 0.7316(3) 0.1226(8) Uani 1 1 d
C15 C 0.8153(2) 0.66445(7) 0.6293(2) 0.0331(4) Uani 1 1 d
C16 C 0.8722(2) 0.69831(8) 0.7643(2) 0.0376(4) Uani 1 1 d
C10 C 0.7341(2) 0.60890(7) 0.6408(2) 0.0328(4) Uani 1 1 d
C5 C 0.5685(2) 0.60492(7) 0.5015(2) 0.0387(4) Uani 1 1 d
C20 C 0.8342(3) 0.68290(9) 0.4842(2) 0.0445(5) Uani 1 1 d
C13 C 0.7698(3) 0.63692(8) 0.9385(2) 0.0417(4) Uani 1 1 d
C11 C 0.8540(3) 0.56130(9) 0.6304(3) 0.0457(5) Uani 1 1 d
C8 C 0.6604(2) 0.60860(7) 0.7885(2) 0.0376(4) Uani 1 1 d
C6 C 0.4324(2) 0.62464(8) 0.5507(3) 0.0448(5) Uani 1 1 d
C7 C 0.4930(3) 0.64199(9) 0.7229(3) 0.0457(5) Uani 1 1 d
C9 C 0.6141(3) 0.55142(9) 0.8324(3) 0.0546(6) Uani 1 1 d
C4 C 0.5439(3) 0.58664(8) 0.3451(3) 0.0506(5) Uani 1 1 d
C17 C 0.9415(3) 0.74935(9) 0.7490(3) 0.0530(6) Uani 1 1 d
C19 C 0.9056(3) 0.73308(10) 0.4712(3) 0.0589(6) Uani 1 1 d
C18 C 0.9578(3) 0.76639(10) 0.6033(3) 0.0613(6) Uani 1 1 d
C12 C 1.0218(3) 0.55735(10) 0.7567(3) 0.0571(6) Uani 1 1 d
C2 C 0.2689(3) 0.62572(10) 0.4433(3) 0.0624(7) Uani 1 1 d
C3 C 0.3798(4) 0.58796(10) 0.2389(3) 0.0647(7) Uani 1 1 d
C1 C 0.2447(4) 0.60666(11) 0.2883(4) 0.0726(8) Uani 1 1 d
C14 C 0.9518(5) 0.71279(12) 1.0589(3) 0.0673(7) Uani 1 1 d
H9A H 0.542(3) 0.5331(11) 0.736(3) 0.062(7) Uiso 1 1 d
H9B H 0.548(4) 0.5543(13) 0.912(4) 0.095(10) Uiso 1 1 d
H9C H 0.715(3) 0.5279(11) 0.875(3) 0.066(7) Uiso 1 1 d
H14A H 0.948(4) 0.6905(12) 1.153(4) 0.083(9) Uiso 1 1 d
H14B H 1.075(4) 0.7174(12) 1.061(3) 0.086(10) Uiso 1 1 d
H14C H 0.893(4) 0.7486(13) 1.057(4) 0.091(10) Uiso 1 1 d
H7A H 0.522(3) 0.6841(10) 0.731(3) 0.051(6) Uiso 1 1 d
H7B H 0.419(3) 0.6346(10) 0.785(3) 0.061(7) Uiso 1 1 d
H20 H 0.794(3) 0.6598(9) 0.389(3) 0.057(6) Uiso 1 1 d
H4 H 0.644(3) 0.5717(10) 0.308(3) 0.059(7) Uiso 1 1 d
H17 H 0.975(3) 0.7731(11) 0.840(3) 0.066(7) Uiso 1 1 d
H1 H 0.130(4) 0.6056(12) 0.211(4) 0.092(9) Uiso 1 1 d
H3 H 0.358(4) 0.5731(11) 0.124(3) 0.080(8) Uiso 1 1 d
H19 H 0.914(4) 0.7445(11) 0.372(4) 0.081(9) Uiso 1 1 d
H2 H 0.176(4) 0.6376(11) 0.483(3) 0.074(8) Uiso 1 1 d
H18 H 1.006(4) 0.8022(12) 0.594(3) 0.078(8) Uiso 1 1 d
H11A H 0.882(3) 0.5648(9) 0.531(3) 0.050(6) Uiso 1 1 d
H11B H 0.795(3) 0.5252(11) 0.627(3) 0.062(7) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0658(9) 0.1217(14) 0.0606(9) 0.0223(9) 0.0047(7) 0.0118(9)
O1 0.0875(12) 0.0710(11) 0.0379(8) 0.0059(7) 0.0261(8) -0.0050(9)
F3 0.0435(8) 0.1054(13) 0.1234(15) 0.0286(11) 0.0048(8) -0.0073(8)
N1 0.0569(10) 0.0432(9) 0.0310(8) -0.0063(7) 0.0109(7) -0.0068(8)
F2 0.0935(13) 0.1218(16) 0.1329(17) -0.0249(13) 0.0016(11) 0.0730(12)
C15 0.0325(9) 0.0345(9) 0.0325(9) -0.0022(7) 0.0097(7) 0.0001(7)
C16 0.0398(10) 0.0373(10) 0.0358(10) -0.0032(8) 0.0112(8) -0.0042(8)
C10 0.0364(9) 0.0294(9) 0.0317(9) -0.0022(7) 0.0087(7) 0.0006(7)
C5 0.0423(10) 0.0293(9) 0.0402(10) -0.0011(7) 0.0049(8) -0.0035(8)
C20 0.0529(12) 0.0469(11) 0.0372(10) -0.0047(9) 0.0186(9) -0.0064(9)
C13 0.0498(11) 0.0435(11) 0.0339(10) 0.0024(8) 0.0156(8) 0.0056(9)
C11 0.0498(12) 0.0408(11) 0.0468(12) -0.0033(9) 0.0144(9) 0.0084(9)
C8 0.0404(10) 0.0348(9) 0.0404(10) 0.0036(8) 0.0161(8) 0.0000(8)
C6 0.0394(10) 0.0363(10) 0.0554(12) 0.0039(9) 0.0085(9) -0.0018(8)
C7 0.0407(10) 0.0463(12) 0.0545(12) 0.0019(10) 0.0207(9) 0.0033(9)
C9 0.0621(15) 0.0418(12) 0.0632(15) 0.0087(11) 0.0231(12) -0.0068(11)
C4 0.0609(13) 0.0382(11) 0.0454(12) -0.0079(9) 0.0036(10) -0.0032(10)
C17 0.0616(13) 0.0464(12) 0.0520(13) -0.0126(10) 0.0181(11) -0.0177(10)
C19 0.0786(16) 0.0566(14) 0.0505(13) 0.0058(11) 0.0331(12) -0.0139(12)
C18 0.0775(16) 0.0465(13) 0.0666(15) -0.0010(11) 0.0314(13) -0.0226(12)
C12 0.0472(12) 0.0591(14) 0.0646(15) 0.0046(11) 0.0153(11) 0.0153(11)
C2 0.0420(12) 0.0581(14) 0.0781(17) 0.0089(12) 0.0031(12) 0.0019(11)
C3 0.0786(17) 0.0479(13) 0.0493(14) -0.0053(11) -0.0109(12) -0.0066(12)
C1 0.0585(15) 0.0586(15) 0.0758(18) 0.0049(13) -0.0203(14) -0.0084(12)
C14 0.097(2) 0.0609(16) 0.0366(12) -0.0119(11) 0.0072(12) -0.0128(15)
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
C16 N1 C14 118.75(18)
C13 N1 C16 123.34(15)
C13 N1 C14 117.79(18)
C16 C15 C10 121.17(15)
C20 C15 C16 118.00(17)
C20 C15 C10 120.83(16)
C15 C16 N1 120.63(16)
C17 C16 N1 119.56(17)
C17 C16 C15 119.79(18)
C15 C10 C5 107.83(14)
C15 C10 C11 111.84(16)
C15 C10 C8 109.53(14)
C5 C10 C11 109.75(15)
C5 C10 C8 100.60(14)
C11 C10 C8 116.45(15)
C6 C5 C10 109.85(16)
C4 C5 C10 129.53(18)
C4 C5 C6 120.60(19)
C15 C20 H20 118.8(14)
C19 C20 C15 121.66(19)
C19 C20 H20 119.6(13)
O1 C13 N1 121.05(19)
O1 C13 C8 121.54(19)
N1 C13 C8 117.25(16)
C10 C11 H11A 107.7(13)
C10 C11 H11B 111.0(14)
C12 C11 C10 118.19(18)
C12 C11 H11A 105.2(14)
C12 C11 H11B 107.2(14)
H11A C11 H11B 106.9(19)
C13 C8 C10 115.41(15)
C13 C8 C7 108.29(16)
C13 C8 C9 109.35(17)
C7 C8 C10 101.77(15)
C9 C8 C10 113.01(17)
C9 C8 C7 108.49(17)
C5 C6 C7 109.96(17)
C5 C6 C2 120.1(2)
C2 C6 C7 129.9(2)
C8 C7 H7A 109.5(12)
C8 C7 H7B 109.6(15)
C6 C7 C8 102.73(16)
C6 C7 H7A 110.3(12)
C6 C7 H7B 116.0(15)
H7A C7 H7B 108.6(19)
C8 C9 H9A 109.7(15)
C8 C9 H9B 109.4(18)
C8 C9 H9C 112.8(15)
H9A C9 H9B 108(2)
H9A C9 H9C 107(2)
H9B C9 H9C 110(2)
C5 C4 C3 118.7(2)
C5 C4 H4 121.0(14)
C3 C4 H4 120.2(13)
C16 C17 H17 119.5(15)
C18 C17 C16 120.6(2)
C18 C17 H17 119.8(15)
C20 C19 H19 119.5(18)
C18 C19 C20 119.9(2)
C18 C19 H19 120.6(18)
C17 C18 H18 120.1(16)
C19 C18 C17 120.0(2)
C19 C18 H18 119.9(16)
F1 C12 F3 103.2(2)
F1 C12 C11 114.65(19)
F3 C12 C11 114.2(2)
F2 C12 F1 105.9(2)
F2 C12 F3 106.5(2)
F2 C12 C11 111.5(2)
C6 C2 H2 118.2(17)
C1 C2 C6 119.0(3)
C1 C2 H2 122.7(17)
C4 C3 H3 119.8(16)
C1 C3 C4 120.6(2)
C1 C3 H3 119.5(16)
C2 C1 H1 121.0(18)
C3 C1 C2 120.9(2)
C3 C1 H1 118.1(18)
N1 C14 H14A 105.8(17)
N1 C14 H14B 108.8(17)
N1 C14 H14C 110.0(18)
H14A C14 H14B 108(2)
H14A C14 H14C 112(2)
H14B C14 H14C 112(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C12 1.328(3)
O1 C13 1.222(2)
F3 C12 1.330(3)
N1 C16 1.414(2)
N1 C13 1.363(3)
N1 C14 1.464(3)
F2 C12 1.323(3)
C15 C16 1.401(2)
C15 C10 1.529(2)
C15 C20 1.388(3)
C16 C17 1.394(3)
C10 C5 1.537(2)
C10 C11 1.542(3)
C10 C8 1.567(2)
C5 C6 1.390(3)
C5 C4 1.388(3)
C20 C19 1.379(3)
C20 H20 0.97(2)
C13 C8 1.519(3)
C11 C12 1.493(3)
C11 H11A 0.96(2)
C11 H11B 1.00(3)
C8 C7 1.556(3)
C8 C9 1.527(3)
C6 C7 1.495(3)
C6 C2 1.393(3)
C7 H7A 1.06(2)
C7 H7B 0.93(3)
C9 H9A 0.99(3)
C9 H9B 1.00(3)
C9 H9C 0.99(3)
C4 C3 1.394(3)
C4 H4 1.03(2)
C17 C18 1.375(3)
C17 H17 0.96(3)
C19 C18 1.371(3)
C19 H19 0.93(3)
C18 H18 0.97(3)
C2 C1 1.384(4)
C2 H2 0.97(3)
C3 C1 1.374(4)
C3 H3 1.03(3)
C1 H1 0.99(3)
C14 H14A 0.99(3)
C14 H14B 1.01(3)
C14 H14C 1.00(3)