#------------------------------------------------------------------------------
#$Date: 2022-03-04 01:16:05 +0200 (Fri, 04 Mar 2022) $
#$Revision: 273289 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/65/1566541.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_1566541
loop_
_publ_author_name
'Yang, Hefei'
'Wang, Le-Cheng'
'Zhang, Yu'
'Zheng, Dongling'
'Chen, Zhengkai'
'Wu, Xiao-Feng'
_publ_section_title
;
 Controllable access to trifluoromethyl-containing indoles and indolines:
 Palladium-catalyzed regioselective functionalization of unactivated
 alkenes with trifluoroacetimidoyl chlorides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00546H
_journal_year                    2022
_chemical_formula_sum            'C22 H15 F3 N3 O'
_chemical_formula_weight         394.37
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2022-01-25 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.651(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.6657(19)
_cell_length_b                   33.014(4)
_cell_length_c                   7.2436(9)
_cell_measurement_reflns_used    2132
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.83
_cell_measurement_theta_min      2.27
_cell_volume                     3703.7(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL(Sheldrick, 2015)'
_computing_publication_material  'WINGX (Farrugia,2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Bruker APEX2 CCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0798
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            23881
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.31
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.911
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1678
_refine_ls_R_factor_gt           0.0789
_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)+(0.1387P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2188
_refine_ls_wR_factor_ref         0.2743
_reflns_number_gt                3645
_reflns_number_total             7525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2sc00546h2.cif
_cod_data_source_block           1_a
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1566541
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.26915(17) 0.28184(8) 0.9600(4) 0.0570(8) Uani 1 1 d . . .
O1 O 0.73913(17) 0.45390(9) 0.3969(4) 0.0614(9) Uani 1 1 d . . .
N5 N 0.40473(19) 0.29022(10) 0.8860(5) 0.0460(8) Uani 1 1 d . . .
N2 N 0.87074(19) 0.45528(10) 0.3037(5) 0.0481(9) Uani 1 1 d . . .
N6 N 0.5905(2) 0.43644(10) 0.5560(5) 0.0537(9) Uani 1 1 d . . .
H6A H 0.6418 0.4424 0.5361 0.064 Uiso 1 1 calc R . .
N3 N 1.1065(2) 0.31107(10) 0.0418(5) 0.0539(9) Uani 1 1 d . . .
H3A H 1.1586 0.3037 0.0345 0.065 Uiso 1 1 calc R . .
N4 N 0.56514(19) 0.28132(10) 0.8207(5) 0.0463(8) Uani 1 1 d . . .
F2 F 0.6761(2) 0.43586(11) 0.9574(5) 0.1197(14) Uani 1 1 d . . .
F3 F 0.6199(2) 0.37865(13) 0.9743(6) 0.1340(17) Uani 1 1 d . . .
N1 N 1.0276(2) 0.47795(11) 0.2661(5) 0.0574(10) Uani 1 1 d . . .
C21 C 0.9634(2) 0.32126(11) -0.0270(6) 0.0435(10) Uani 1 1 d . . .
F1 F 0.7067(2) 0.38942(13) 0.7896(6) 0.1260(14) Uani 1 1 d . . .
C42 C 0.4463(2) 0.43062(11) 0.5215(5) 0.0408(9) Uani 1 1 d . . .
C17 C 1.0361(2) 0.30465(11) -0.0906(6) 0.0476(10) Uani 1 1 d . . .
C29 C 0.4346(2) 0.25034(11) 0.8782(5) 0.0398(9) Uani 1 1 d . . .
C30 C 0.5208(2) 0.24680(11) 0.8425(5) 0.0399(9) Uani 1 1 d . . .
C31 C 0.3271(2) 0.30392(12) 0.9257(6) 0.0449(10) Uani 1 1 d . . .
C28 C 0.3885(3) 0.21603(12) 0.9028(5) 0.0484(10) Uani 1 1 d . . .
H28 H 0.3322 0.2181 0.9283 0.058 Uiso 1 1 calc R . .
C25 C 0.5576(3) 0.20758(12) 0.8294(5) 0.0463(10) Uani 1 1 d . . .
C37 C 0.5161(3) 0.44493(12) 0.4390(6) 0.0480(10) Uani 1 1 d . . .
C10 C 0.8036(2) 0.43639(12) 0.3634(6) 0.0458(10) Uani 1 1 d . . .
C35 C 0.4820(2) 0.41236(11) 0.6969(6) 0.0461(10) Uani 1 1 d . . .
C13 C 0.9423(2) 0.35804(12) 0.2826(6) 0.0483(10) Uani 1 1 d . . .
H13 H 0.9707 0.3622 0.4034 0.058 Uiso 1 1 calc R . .
C14 C 0.9925(2) 0.33853(11) 0.1551(6) 0.0442(10) Uani 1 1 d . . .
C36 C 0.5702(2) 0.41689(12) 0.7099(6) 0.0495(10) Uani 1 1 d . . .
C33 C 0.3622(2) 0.37228(12) 0.7918(6) 0.0473(10) Uani 1 1 d . . .
H33 H 0.3346 0.3730 0.6689 0.057 Uiso 1 1 calc R . .
C34 C 0.4361(2) 0.39158(12) 0.8311(6) 0.0484(10) Uani 1 1 d . . .
H34 H 0.4616 0.3921 0.9556 0.058 Uiso 1 1 calc R . .
C44 C 0.8837(3) 0.31795(12) -0.1440(6) 0.0523(11) Uani 1 1 d . . .
H44 H 0.8342 0.3288 -0.1069 0.063 Uiso 1 1 calc R . .
C9 C 0.9667(3) 0.50760(13) 0.2454(5) 0.0492(10) Uani 1 1 d . . .
C32 C 0.3191(3) 0.34922(12) 0.9308(7) 0.0554(11) Uani 1 1 d . . .
H32A H 0.2582 0.3561 0.9108 0.066 Uiso 1 1 calc R . .
H32B H 0.3430 0.3584 1.0550 0.066 Uiso 1 1 calc R . .
C41 C 0.3626(3) 0.43722(13) 0.4266(6) 0.0541(11) Uani 1 1 d . . .
H41 H 0.3149 0.4289 0.4792 0.065 Uiso 1 1 calc R . .
C15 C 1.0801(2) 0.33114(12) 0.1873(6) 0.0497(10) Uani 1 1 d . . .
C11 C 0.8157(3) 0.39115(13) 0.3913(7) 0.0579(12) Uani 1 1 d . . .
H11A H 0.8480 0.3864 0.5145 0.070 Uiso 1 1 calc R . .
H11B H 0.7594 0.3787 0.3878 0.070 Uiso 1 1 calc R . .
F6 F 1.2172(2) 0.35319(18) 0.3005(6) 0.174(2) Uani 1 1 d . . .
C12 C 0.8618(3) 0.37063(12) 0.2493(6) 0.0522(11) Uani 1 1 d . . .
H12 H 0.8314 0.3666 0.1302 0.063 Uiso 1 1 calc R . .
C27 C 0.4257(3) 0.17799(13) 0.8897(6) 0.0561(11) Uani 1 1 d . . .
H27 H 0.3931 0.1550 0.9057 0.067 Uiso 1 1 calc R . .
C8 C 0.8814(3) 0.49649(12) 0.2684(6) 0.0482(10) Uani 1 1 d . . .
C18 C 1.0309(3) 0.28447(13) -0.2618(7) 0.0572(11) Uani 1 1 d . . .
H18 H 1.0797 0.2730 -0.2995 0.069 Uiso 1 1 calc R . .
C22 C 0.6457(2) 0.27763(14) 0.7863(6) 0.0550(11) Uani 1 1 d . . .
H22 H 0.6762 0.3012 0.7698 0.066 Uiso 1 1 calc R . .
C26 C 0.5076(3) 0.17329(13) 0.8546(6) 0.0587(12) Uani 1 1 d . . .
H26 H 0.5306 0.1475 0.8472 0.070 Uiso 1 1 calc R . .
C38 C 0.5055(3) 0.46462(13) 0.2661(7) 0.0605(12) Uani 1 1 d . . .
H38 H 0.5524 0.4740 0.2135 0.073 Uiso 1 1 calc R . .
C19 C 0.9529(3) 0.28219(13) -0.3712(7) 0.0637(12) Uani 1 1 d . . .
H19 H 0.9483 0.2694 -0.4867 0.076 Uiso 1 1 calc R . .
C24 C 0.6439(3) 0.20602(15) 0.7934(6) 0.0597(12) Uani 1 1 d . . .
H24 H 0.6706 0.1811 0.7836 0.072 Uiso 1 1 calc R . .
C4 C 0.9856(4) 0.54807(15) 0.2005(6) 0.0663(13) Uani 1 1 d . . .
C23 C 0.6874(3) 0.24059(16) 0.7733(7) 0.0623(12) Uani 1 1 d . . .
H23 H 0.7443 0.2398 0.7512 0.075 Uiso 1 1 calc R . .
C43 C 0.6400(3) 0.40487(15) 0.8558(7) 0.0626(12) Uani 1 1 d . . .
F4 F 1.1237(3) 0.3665(2) 0.4575(9) 0.246(4) Uani 1 1 d . . .
C16 C 1.1441(3) 0.34358(18) 0.3434(9) 0.0720(14) Uani 1 1 d . . .
C20 C 0.8790(3) 0.29873(13) -0.3130(7) 0.0614(12) Uani 1 1 d . . .
H20 H 0.8260 0.2967 -0.3901 0.074 Uiso 1 1 calc R . .
C7 C 0.8174(3) 0.52480(14) 0.2509(7) 0.0703(14) Uani 1 1 d . . .
H7 H 0.7616 0.5179 0.2680 0.084 Uiso 1 1 calc R . .
F5 F 1.1734(3) 0.3129(2) 0.4528(8) 0.192(3) Uani 1 1 d . . .
C39 C 0.4221(3) 0.46941(15) 0.1783(7) 0.0731(14) Uani 1 1 d . . .
H39 H 0.4126 0.4821 0.0625 0.088 Uiso 1 1 calc R . .
C40 C 0.3517(3) 0.45596(15) 0.2561(7) 0.0697(14) Uani 1 1 d . . .
H40 H 0.2963 0.4597 0.1917 0.084 Uiso 1 1 calc R . .
C1 C 1.1067(3) 0.48778(18) 0.2449(7) 0.0758(15) Uani 1 1 d . . .
H1 H 1.1491 0.4678 0.2619 0.091 Uiso 1 1 calc R . .
C3 C 1.0702(4) 0.5568(2) 0.1757(8) 0.0875(19) Uani 1 1 d . . .
H3 H 1.0851 0.5829 0.1444 0.105 Uiso 1 1 calc R . .
C2 C 1.1303(4) 0.5272(2) 0.1973(8) 0.0878(19) Uani 1 1 d . . .
H2 H 1.1868 0.5328 0.1810 0.105 Uiso 1 1 calc R . .
C6 C 0.8382(5) 0.56488(17) 0.2061(9) 0.0951(19) Uani 1 1 d . . .
H6 H 0.7946 0.5842 0.1923 0.114 Uiso 1 1 calc R . .
C5 C 0.9178(5) 0.57631(17) 0.1825(9) 0.101(2) Uani 1 1 d . . .
H5 H 0.9283 0.6032 0.1541 0.121 Uiso 1 1 calc R . .
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'
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
C31 N5 C29 129.2(3) . . ?
C10 N2 C8 129.0(3) . . ?
C37 N6 C36 108.8(3) . . ?
C37 N6 H6A 125.6 . . ?
C36 N6 H6A 125.6 . . ?
C15 N3 C17 108.2(3) . . ?
C15 N3 H3A 125.9 . . ?
C17 N3 H3A 125.9 . . ?
C22 N4 C30 117.5(3) . . ?
C1 N1 C9 117.9(4) . . ?
C17 C21 C44 117.6(4) . . ?
C17 C21 C14 107.1(3) . . ?
C44 C21 C14 135.3(4) . . ?
C41 C42 C37 118.0(4) . . ?
C41 C42 C35 135.1(4) . . ?
C37 C42 C35 106.9(3) . . ?
N3 C17 C18 129.0(4) . . ?
N3 C17 C21 108.6(4) . . ?
C18 C17 C21 122.4(4) . . ?
C28 C29 N5 125.9(4) . . ?
C28 C29 C30 119.4(4) . . ?
N5 C29 C30 114.7(3) . . ?
N4 C30 C29 118.1(3) . . ?
N4 C30 C25 122.4(3) . . ?
C29 C30 C25 119.5(3) . . ?
O2 C31 N5 123.9(4) . . ?
O2 C31 C32 121.6(4) . . ?
N5 C31 C32 114.5(3) . . ?
C29 C28 C27 120.2(4) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C26 C25 C24 124.2(4) . . ?
C26 C25 C30 119.0(4) . . ?
C24 C25 C30 116.9(4) . . ?
N6 C37 C38 128.8(4) . . ?
N6 C37 C42 108.3(4) . . ?
C38 C37 C42 122.8(4) . . ?
O1 C10 N2 123.6(4) . . ?
O1 C10 C11 122.1(4) . . ?
N2 C10 C11 114.3(3) . . ?
C36 C35 C42 105.5(4) . . ?
C36 C35 C34 126.4(4) . . ?
C42 C35 C34 128.0(3) . . ?
C12 C13 C14 128.3(4) . . ?
C12 C13 H13 115.8 . . ?
C14 C13 H13 115.8 . . ?
C15 C14 C21 104.7(3) . . ?
C15 C14 C13 126.3(4) . . ?
C21 C14 C13 129.0(3) . . ?
N6 C36 C35 110.4(4) . . ?
N6 C36 C43 118.6(4) . . ?
C35 C36 C43 130.9(4) . . ?
C34 C33 C32 124.9(4) . . ?
C34 C33 H33 117.6 . . ?
C32 C33 H33 117.6 . . ?
C33 C34 C35 126.1(4) . . ?
C33 C34 H34 117.0 . . ?
C35 C34 H34 117.0 . . ?
C20 C44 C21 119.9(4) . . ?
C20 C44 H44 120.0 . . ?
C21 C44 H44 120.0 . . ?
N1 C9 C4 122.4(4) . . ?
N1 C9 C8 117.3(4) . . ?
C4 C9 C8 120.3(4) . . ?
C33 C32 C31 116.2(3) . . ?
C33 C32 H32A 108.2 . . ?
C31 C32 H32A 108.2 . . ?
C33 C32 H32B 108.2 . . ?
C31 C32 H32B 108.2 . . ?
H32A C32 H32B 107.4 . . ?
C40 C41 C42 119.5(4) . . ?
C40 C41 H41 120.2 . . ?
C42 C41 H41 120.2 . . ?
N3 C15 C14 111.5(4) . . ?
N3 C15 C16 119.0(4) . . ?
C14 C15 C16 129.4(4) . . ?
C12 C11 C10 114.6(4) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 124.2(4) . . ?
C13 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
C26 C27 C28 122.2(4) . . ?
C26 C27 H27 118.9 . . ?
C28 C27 H27 118.9 . . ?
C7 C8 N2 125.2(4) . . ?
C7 C8 C9 120.3(4) . . ?
N2 C8 C9 114.4(3) . . ?
C19 C18 C17 118.1(4) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
N4 C22 C23 124.1(4) . . ?
N4 C22 H22 118.0 . . ?
C23 C22 H22 118.0 . . ?
C27 C26 C25 119.7(4) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C39 C38 C37 116.4(4) . . ?
C39 C38 H38 121.8 . . ?
C37 C38 H38 121.8 . . ?
C18 C19 C20 121.1(4) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C23 C24 C25 120.1(4) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C3 C4 C5 124.9(5) . . ?
C3 C4 C9 117.4(5) . . ?
C5 C4 C9 117.7(5) . . ?
C24 C23 C22 119.0(4) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
F3 C43 F1 105.6(4) . . ?
F3 C43 F2 105.8(5) . . ?
F1 C43 F2 101.8(4) . . ?
F3 C43 C36 115.7(4) . . ?
F1 C43 C36 113.1(4) . . ?
F2 C43 C36 113.6(4) . . ?
F4 C16 F6 110.7(6) . . ?
F4 C16 F5 100.1(6) . . ?
F6 C16 F5 95.4(5) . . ?
F4 C16 C15 119.4(4) . . ?
F6 C16 C15 115.0(5) . . ?
F5 C16 C15 112.6(5) . . ?
C44 C20 C19 120.9(4) . . ?
C44 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C8 C7 C6 118.1(5) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C38 C39 C40 122.3(5) . . ?
C38 C39 H39 118.8 . . ?
C40 C39 H39 118.8 . . ?
C41 C40 C39 120.9(4) . . ?
C41 C40 H40 119.6 . . ?
C39 C40 H40 119.6 . . ?
N1 C1 C2 122.9(5) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C2 C3 C4 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C5 C6 C7 123.1(5) . . ?
C5 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
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
O2 C31 1.219(4) . ?
O1 C10 1.220(4) . ?
N5 C31 1.368(5) . ?
N5 C29 1.401(5) . ?
N2 C10 1.348(5) . ?
N2 C8 1.399(5) . ?
N6 C37 1.364(5) . ?
N6 C36 1.367(5) . ?
N6 H6A 0.8600 . ?
N3 C15 1.361(5) . ?
N3 C17 1.365(5) . ?
N3 H3A 0.8600 . ?
N4 C22 1.328(5) . ?
N4 C30 1.356(5) . ?
F2 C43 1.335(5) . ?
F3 C43 1.291(5) . ?
N1 C1 1.312(5) . ?
N1 C9 1.360(5) . ?
C21 C17 1.403(5) . ?
C21 C44 1.404(5) . ?
C21 C14 1.446(6) . ?
F1 C43 1.316(6) . ?
C42 C41 1.402(5) . ?
C42 C37 1.405(5) . ?
C42 C35 1.441(6) . ?
C17 C18 1.399(6) . ?
C29 C28 1.369(5) . ?
C29 C30 1.418(5) . ?
C30 C25 1.426(5) . ?
C31 C32 1.502(6) . ?
C28 C27 1.394(6) . ?
C28 H28 0.9300 . ?
C25 C26 1.404(6) . ?
C25 C24 1.416(6) . ?
C37 C38 1.398(6) . ?
C10 C11 1.515(6) . ?
C35 C36 1.379(5) . ?
C35 C34 1.464(5) . ?
C13 C12 1.315(5) . ?
C13 C14 1.451(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(5) . ?
C36 C43 1.456(6) . ?
C33 C34 1.314(5) . ?
C33 C32 1.501(5) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C44 C20 1.371(6) . ?
C44 H44 0.9300 . ?
C9 C4 1.417(6) . ?
C9 C8 1.419(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C41 C40 1.369(6) . ?
C41 H41 0.9300 . ?
C15 C16 1.453(7) . ?
C11 C12 1.504(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
F6 C16 1.270(6) . ?
C12 H12 0.9300 . ?
C27 C26 1.354(6) . ?
C27 H27 0.9300 . ?
C8 C7 1.363(6) . ?
C18 C19 1.355(6) . ?
C18 H18 0.9300 . ?
C22 C23 1.396(6) . ?
C22 H22 0.9300 . ?
C26 H26 0.9300 . ?
C38 C39 1.372(6) . ?
C38 H38 0.9300 . ?
C19 C20 1.401(6) . ?
C19 H19 0.9300 . ?
C24 C23 1.348(6) . ?
C24 H24 0.9300 . ?
C4 C3 1.393(7) . ?
C4 C5 1.405(8) . ?
C23 H23 0.9300 . ?
F4 C16 1.199(6) . ?
C16 F5 1.326(7) . ?
C20 H20 0.9300 . ?
C7 C6 1.412(7) . ?
C7 H7 0.9300 . ?
C39 C40 1.385(6) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C1 C2 1.409(8) . ?
C1 H1 0.9300 . ?
C3 C2 1.349(8) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C6 C5 1.338(8) . ?
C6 H6 0.9300 . ?
C5 H5 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
C15 N3 C17 C18 -178.3(4) . . . . ?
C15 N3 C17 C21 0.2(5) . . . . ?
C44 C21 C17 N3 179.8(3) . . . . ?
C14 C21 C17 N3 -0.2(4) . . . . ?
C44 C21 C17 C18 -1.6(6) . . . . ?
C14 C21 C17 C18 178.5(4) . . . . ?
C31 N5 C29 C28 2.8(6) . . . . ?
C31 N5 C29 C30 -176.7(4) . . . . ?
C22 N4 C30 C29 -179.6(3) . . . . ?
C22 N4 C30 C25 -0.1(5) . . . . ?
C28 C29 C30 N4 -179.3(3) . . . . ?
N5 C29 C30 N4 0.3(5) . . . . ?
C28 C29 C30 C25 1.2(5) . . . . ?
N5 C29 C30 C25 -179.3(3) . . . . ?
C29 N5 C31 O2 -0.8(7) . . . . ?
C29 N5 C31 C32 177.1(4) . . . . ?
N5 C29 C28 C27 179.4(4) . . . . ?
C30 C29 C28 C27 -1.1(6) . . . . ?
N4 C30 C25 C26 179.7(4) . . . . ?
C29 C30 C25 C26 -0.8(5) . . . . ?
N4 C30 C25 C24 0.5(6) . . . . ?
C29 C30 C25 C24 180.0(3) . . . . ?
C36 N6 C37 C38 179.8(4) . . . . ?
C36 N6 C37 C42 0.4(5) . . . . ?
C41 C42 C37 N6 178.3(3) . . . . ?
C35 C42 C37 N6 -0.5(4) . . . . ?
C41 C42 C37 C38 -1.2(6) . . . . ?
C35 C42 C37 C38 -179.9(4) . . . . ?
C8 N2 C10 O1 -0.1(7) . . . . ?
C8 N2 C10 C11 -178.4(4) . . . . ?
C41 C42 C35 C36 -178.1(4) . . . . ?
C37 C42 C35 C36 0.3(4) . . . . ?
C41 C42 C35 C34 4.4(7) . . . . ?
C37 C42 C35 C34 -177.1(4) . . . . ?
C17 C21 C14 C15 0.1(4) . . . . ?
C44 C21 C14 C15 -179.9(4) . . . . ?
C17 C21 C14 C13 -177.7(4) . . . . ?
C44 C21 C14 C13 2.4(7) . . . . ?
C12 C13 C14 C15 169.9(4) . . . . ?
C12 C13 C14 C21 -12.8(7) . . . . ?
C37 N6 C36 C35 -0.2(5) . . . . ?
C37 N6 C36 C43 -179.8(4) . . . . ?
C42 C35 C36 N6 -0.1(5) . . . . ?
C34 C35 C36 N6 177.5(4) . . . . ?
C42 C35 C36 C43 179.4(4) . . . . ?
C34 C35 C36 C43 -3.1(7) . . . . ?
C32 C33 C34 C35 176.3(4) . . . . ?
C36 C35 C34 C33 -149.2(4) . . . . ?
C42 C35 C34 C33 27.8(7) . . . . ?
C17 C21 C44 C20 0.5(6) . . . . ?
C14 C21 C44 C20 -179.5(4) . . . . ?
C1 N1 C9 C4 0.6(6) . . . . ?
C1 N1 C9 C8 179.9(4) . . . . ?
C34 C33 C32 C31 -102.7(5) . . . . ?
O2 C31 C32 C33 -146.0(4) . . . . ?
N5 C31 C32 C33 36.1(5) . . . . ?
C37 C42 C41 C40 2.1(6) . . . . ?
C35 C42 C41 C40 -179.7(5) . . . . ?
C17 N3 C15 C14 -0.2(5) . . . . ?
C17 N3 C15 C16 -176.8(4) . . . . ?
C21 C14 C15 N3 0.0(5) . . . . ?
C13 C14 C15 N3 177.9(4) . . . . ?
C21 C14 C15 C16 176.2(5) . . . . ?
C13 C14 C15 C16 -6.0(7) . . . . ?
O1 C10 C11 C12 144.3(4) . . . . ?
N2 C10 C11 C12 -37.3(5) . . . . ?
C14 C13 C12 C11 -179.1(4) . . . . ?
C10 C11 C12 C13 105.4(5) . . . . ?
C29 C28 C27 C26 0.6(6) . . . . ?
C10 N2 C8 C7 -14.5(7) . . . . ?
C10 N2 C8 C9 167.2(4) . . . . ?
N1 C9 C8 C7 179.5(4) . . . . ?
C4 C9 C8 C7 -1.2(6) . . . . ?
N1 C9 C8 N2 -2.1(5) . . . . ?
C4 C9 C8 N2 177.1(4) . . . . ?
N3 C17 C18 C19 -179.6(4) . . . . ?
C21 C17 C18 C19 2.0(6) . . . . ?
C30 N4 C22 C23 -0.7(6) . . . . ?
C28 C27 C26 C25 -0.3(7) . . . . ?
C24 C25 C26 C27 179.5(4) . . . . ?
C30 C25 C26 C27 0.4(6) . . . . ?
N6 C37 C38 C39 -179.5(4) . . . . ?
C42 C37 C38 C39 -0.2(7) . . . . ?
C17 C18 C19 C20 -1.4(7) . . . . ?
C26 C25 C24 C23 -179.2(4) . . . . ?
C30 C25 C24 C23 0.0(6) . . . . ?
N1 C9 C4 C3 0.7(6) . . . . ?
C8 C9 C4 C3 -178.6(4) . . . . ?
N1 C9 C4 C5 -179.9(4) . . . . ?
C8 C9 C4 C5 0.8(7) . . . . ?
C25 C24 C23 C22 -0.8(7) . . . . ?
N4 C22 C23 C24 1.2(7) . . . . ?
N6 C36 C43 F3 -164.3(5) . . . . ?
C35 C36 C43 F3 16.3(8) . . . . ?
N6 C36 C43 F1 -42.4(6) . . . . ?
C35 C36 C43 F1 138.2(5) . . . . ?
N6 C36 C43 F2 73.0(6) . . . . ?
C35 C36 C43 F2 -106.4(6) . . . . ?
N3 C15 C16 F4 168.5(7) . . . . ?
C14 C15 C16 F4 -7.4(10) . . . . ?
N3 C15 C16 F6 33.3(7) . . . . ?
C14 C15 C16 F6 -142.6(5) . . . . ?
N3 C15 C16 F5 -74.6(7) . . . . ?
C14 C15 C16 F5 109.5(6) . . . . ?
C21 C44 C20 C19 0.1(7) . . . . ?
C18 C19 C20 C44 0.4(7) . . . . ?
N2 C8 C7 C6 -177.0(5) . . . . ?
C9 C8 C7 C6 1.2(7) . . . . ?
C37 C38 C39 C40 0.7(7) . . . . ?
C42 C41 C40 C39 -1.7(7) . . . . ?
C38 C39 C40 C41 0.3(8) . . . . ?
C9 N1 C1 C2 -1.6(7) . . . . ?
C5 C4 C3 C2 179.7(6) . . . . ?
C9 C4 C3 C2 -0.9(7) . . . . ?
C4 C3 C2 C1 0.0(8) . . . . ?
N1 C1 C2 C3 1.4(8) . . . . ?
C8 C7 C6 C5 -0.9(9) . . . . ?
C7 C6 C5 C4 0.5(10) . . . . ?
C3 C4 C5 C6 178.9(6) . . . . ?
C9 C4 C5 C6 -0.5(8) . . . . ?
