#------------------------------------------------------------------------------
#$Date: 2022-03-04 01:16:05 +0200 (Fri, 04 Mar 2022) $
#$Revision: 273289 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/65/1566540.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_1566540
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_moiety         'C21 H15 Cl F3 N3 O2'
_chemical_formula_sum            'C21 H15 Cl F3 N3 O2'
_chemical_formula_weight         433.81
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2022-01-25 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.523(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.287(5)
_cell_length_b                   15.859(5)
_cell_length_c                   17.629(6)
_cell_measurement_reflns_used    4497
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.10
_cell_measurement_theta_min      2.30
_cell_volume                     3888(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23729
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         1.806
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         8818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0562
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5022
_reflns_number_total             8818
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00546h2.cif
_cod_data_source_block           cfk_0m
_cod_database_code               1566540
_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   0.964
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.07) H3(0.074) H6(0.056) H7A(0.065) H7B(0.065) H8(0.07)
 H11A(0.071) H11B(0.071) H14(0.088) H15(0.103) H16(0.093) H19(0.089) H20(0.101)
 H21(0.092) H23(0.073) H24(0.075) H27(0.06) H30A(0.072) H30B(0.072) H31(0.055)
 H32A(0.07) H32B(0.07) H35(0.086) H36(0.103) H37(0.097) H40(0.107) H41(0.122)
 H42(0.107)
 Fixed X: H2(1.053539) H3(0.893286) H6(1.093717) H7A(0.764928) H7B(0.771072)
 H8(0.785596) H11A(0.72311) H11B(0.733585) H14(0.431275) H15(0.269529)
 H16(0.19283) H19(0.451151) H20(0.291407) H21(0.201971) H23(0.34176)
 H24(0.50345) H27(0.297895) H30A(0.632968) H30B(0.590323) H31(0.619133)
 H32A(0.663172) H32B(0.653735) H35(0.959014) H36(1.126577) H37(1.20662)
 H40(1.200574) H41(1.108286) H42(0.941618)
 Fixed Y: H2(0.490649) H3(0.508083) H6(0.360324) H7A(0.336155) H7B(0.411598)
 H8(0.507173) H11A(0.474721) H11B(0.378095) H14(0.429846) H15(0.392655)
 H16(0.341757) H19(0.328219) H20(0.288647) H21(0.29711) H23(0.212482)
 H24(0.230903) H27(0.121247) H30A(0.139384) H30B(0.230513) H31(0.256428)
 H32A(0.146046) H32B(0.081911) H35(0.180597) H36(0.178446) H37(0.129809)
 H40(0.064339) H41(0.017962) H42(0.017761)
 Fixed Z: H2(0.730626) H3(0.644019) H6(0.552628) H7A(0.413665) H7B(0.357775)
 H8(0.453887) H11A(0.548989) H11B(0.536648) H14(0.309746) H15(0.247851)
 H16(0.323703) H19(0.661708) H20(0.606341) H21(0.465732) H23(0.16817)
 H24(0.252584) H27(0.362625) H30A(0.540125) H30B(0.537032) H31(0.42727)
 H32A(0.356179) H32B(0.420025) H35(0.600746) H36(0.657173) H37(0.583128)
 H40(0.450272) H41(0.318059) H42(0.269213)
;
_shelx_shelxl_version_number     2016/6
_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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.18523(6) 0.15102(6) 0.19421(4) 0.0777(3) Uani 1 1 d . . . . .
Cl2 Cl 1.20923(5) 0.41671(5) 0.71408(4) 0.0685(2) Uani 1 1 d . . . . .
F1 F 0.83348(15) 0.36831(12) 0.25513(10) 0.0892(6) Uani 1 1 d . . . . .
F2 F 0.91942(17) 0.25851(15) 0.27021(12) 0.1200(8) Uani 1 1 d . . . . .
F3 F 0.80115(16) 0.25630(12) 0.30370(12) 0.0972(7) Uani 1 1 d . . . . .
F4 F 0.4677(2) 0.0647(2) 0.65708(13) 0.1662(14) Uani 1 1 d . . . . .
F5 F 0.5905(2) 0.04810(14) 0.63402(12) 0.1191(9) Uani 1 1 d . . . . .
F6 F 0.55105(16) 0.16839(12) 0.65366(10) 0.0926(6) Uani 1 1 d . . . . .
O1 O 0.60013(15) 0.43776(15) 0.36746(12) 0.0767(6) Uani 1 1 d . . . . .
O2 O 1.02695(16) 0.31709(14) 0.41399(12) 0.0739(6) Uani 1 1 d . . . . .
O3 O 0.79165(14) 0.20081(14) 0.53494(12) 0.0779(6) Uani 1 1 d . . . . .
O4 O 0.37351(17) 0.06871(17) 0.49994(13) 0.0945(8) Uani 1 1 d . . . . .
N1 N 0.90297(15) 0.36950(12) 0.43858(12) 0.0483(5) Uani 1 1 d . . . . .
N2 N 0.55092(16) 0.41584(13) 0.46991(14) 0.0520(5) Uani 1 1 d . . . . .
N3 N 0.45886(16) 0.36099(14) 0.55846(14) 0.0577(6) Uani 1 1 d . . . . .
N4 N 0.48728(14) 0.14291(12) 0.47744(11) 0.0451(5) Uani 1 1 d . . . . .
N5 N 0.83885(16) 0.12322(16) 0.45184(15) 0.0581(6) Uani 1 1 d . . . . .
N6 N 0.93332(18) 0.06716(16) 0.36636(15) 0.0649(6) Uani 1 1 d . . . . .
C1 C 1.08774(19) 0.42552(15) 0.64918(15) 0.0487(6) Uani 1 1 d . . . . .
C2 C 1.0288(2) 0.46843(17) 0.67697(16) 0.0580(7) Uani 1 1 d . . . . .
H2 H 1.053539 0.490649 0.730626 0.070 Uiso 1 1 calc R U . . .
C3 C 0.9332(2) 0.47852(18) 0.62542(17) 0.0614(7) Uani 1 1 d . . . . .
H3 H 0.893286 0.508083 0.644019 0.074 Uiso 1 1 calc R U . . .
C4 C 0.89623(19) 0.44496(16) 0.54630(16) 0.0511(6) Uani 1 1 d . . . . .
C5 C 0.95679(18) 0.39978(14) 0.52063(14) 0.0438(6) Uani 1 1 d . . . . .
C6 C 1.05346(18) 0.38983(15) 0.57085(14) 0.0469(6) Uani 1 1 d . . . . .
H6 H 1.093717 0.360324 0.552628 0.056 Uiso 1 1 calc R U . . .
C7 C 0.79942(18) 0.38738(17) 0.41329(16) 0.0541(6) Uani 1 1 d . . . . .
H7A H 0.764928 0.336155 0.413665 0.065 Uiso 1 1 calc R U . . .
H7B H 0.771072 0.411598 0.357775 0.065 Uiso 1 1 calc R U . . .
C8 C 0.7958(2) 0.45040(18) 0.47798(17) 0.0583(7) Uani 1 1 d . . . . .
H8 H 0.785596 0.507173 0.453887 0.070 Uiso 1 1 calc R U . . .
C9 C 0.9424(2) 0.33054(17) 0.39229(16) 0.0537(6) Uani 1 1 d . . . . .
C10 C 0.8730(2) 0.3034(2) 0.30455(18) 0.0680(8) Uani 1 1 d . . . . .
C11 C 0.71979(19) 0.43216(19) 0.50836(17) 0.0593(7) Uani 1 1 d . . . . .
H11A H 0.723110 0.474721 0.548989 0.071 Uiso 1 1 calc R U . . .
H11B H 0.733585 0.378095 0.536648 0.071 Uiso 1 1 calc R U . . .
C12 C 0.6181(2) 0.43012(16) 0.44049(17) 0.0517(6) Uani 1 1 d . . . . .
C13 C 0.45266(18) 0.39859(16) 0.42597(16) 0.0495(6) Uani 1 1 d . . . . .
C14 C 0.4016(2) 0.4085(2) 0.34224(18) 0.0733(9) Uani 1 1 d . . . . .
H14 H 0.431275 0.429846 0.309746 0.088 Uiso 1 1 calc R U . . .
C15 C 0.3036(2) 0.3862(2) 0.3051(2) 0.0859(10) Uani 1 1 d . . . . .
H15 H 0.269529 0.392655 0.247851 0.103 Uiso 1 1 calc R U . . .
C16 C 0.2576(2) 0.3559(2) 0.3500(2) 0.0773(9) Uani 1 1 d . . . . .
H16 H 0.192830 0.341757 0.323703 0.093 Uiso 1 1 calc R U . . .
C17 C 0.30737(19) 0.34569(16) 0.43597(19) 0.0588(7) Uani 1 1 d . . . . .
C18 C 0.40569(18) 0.36783(15) 0.47488(16) 0.0487(6) Uani 1 1 d . . . . .
C19 C 0.4155(2) 0.3325(2) 0.6044(2) 0.0741(9) Uani 1 1 d . . . . .
H19 H 0.451151 0.328219 0.661708 0.089 Uiso 1 1 calc R U . . .
C20 C 0.3189(3) 0.3084(2) 0.5715(3) 0.0843(10) Uani 1 1 d . . . . .
H20 H 0.291407 0.288647 0.606341 0.101 Uiso 1 1 calc R U . . .
C21 C 0.2660(2) 0.3141(2) 0.4885(2) 0.0767(9) Uani 1 1 d . . . . .
H21 H 0.201971 0.297110 0.465732 0.092 Uiso 1 1 calc R U . . .
C22 C 0.3069(2) 0.16461(17) 0.25740(15) 0.0540(7) Uani 1 1 d . . . . .
C23 C 0.3662(2) 0.19787(17) 0.22428(16) 0.0612(7) Uani 1 1 d . . . . .
H23 H 0.341760 0.212482 0.168170 0.073 Uiso 1 1 calc R U . . .
C24 C 0.4624(2) 0.20948(18) 0.27475(16) 0.0624(7) Uani 1 1 d . . . . .
H24 H 0.503450 0.230903 0.252584 0.075 Uiso 1 1 calc R U . . .
C25 C 0.49775(17) 0.18904(15) 0.35884(14) 0.0448(6) Uani 1 1 d . . . . .
C26 C 0.43590(17) 0.15644(14) 0.39012(13) 0.0417(5) Uani 1 1 d . . . . .
C27 C 0.33904(18) 0.14324(16) 0.34086(14) 0.0502(6) Uani 1 1 d . . . . .
H27 H 0.297895 0.121247 0.362625 0.060 Uiso 1 1 calc R U . . .
C28 C 0.4517(2) 0.10217(18) 0.52497(16) 0.0562(7) Uani 1 1 d . . . . .
C29 C 0.5149(2) 0.0967(2) 0.61792(17) 0.0677(8) Uani 1 1 d . . . . .
C30 C 0.58485(19) 0.1792(2) 0.50541(16) 0.0601(7) Uani 1 1 d . . . . .
H30A H 0.632968 0.139384 0.540125 0.072 Uiso 1 1 calc R U . . .
H30B H 0.590323 0.230513 0.537032 0.072 Uiso 1 1 calc R U . . .
C31 C 0.59788(17) 0.19791(15) 0.42580(14) 0.0461(6) Uani 1 1 d . . . . .
H31 H 0.619133 0.256428 0.427270 0.055 Uiso 1 1 calc R U . . .
C32 C 0.66927(18) 0.13984(18) 0.41290(17) 0.0584(7) Uani 1 1 d . . . . .
H32A H 0.663172 0.146046 0.356179 0.070 Uiso 1 1 calc R U . . .
H32B H 0.653735 0.081911 0.420025 0.070 Uiso 1 1 calc R U . . .
C33 C 0.77256(19) 0.15766(17) 0.47285(16) 0.0535(6) Uani 1 1 d . . . . .
C34 C 0.93914(18) 0.12827(16) 0.49137(16) 0.0532(6) Uani 1 1 d . . . . .
C35 C 0.9906(2) 0.1592(2) 0.56978(18) 0.0720(8) Uani 1 1 d . . . . .
H35 H 0.959014 0.180597 0.600746 0.086 Uiso 1 1 calc R U . . .
C36 C 1.0919(2) 0.1583(2) 0.6034(2) 0.0857(10) Uani 1 1 d . . . . .
H36 H 1.126577 0.178446 0.657173 0.103 Uiso 1 1 calc R U . . .
C37 C 1.1398(2) 0.1290(2) 0.5596(2) 0.0811(9) Uani 1 1 d . . . . .
H37 H 1.206620 0.129809 0.583128 0.097 Uiso 1 1 calc R U . . .
C38 C 1.0893(2) 0.09747(18) 0.4788(2) 0.0652(8) Uani 1 1 d . . . . .
C39 C 0.98802(19) 0.09709(17) 0.44406(17) 0.0547(7) Uani 1 1 d . . . . .
C40 C 1.1339(3) 0.0659(2) 0.4296(3) 0.0888(11) Uani 1 1 d . . . . .
H40 H 1.200574 0.064339 0.450272 0.107 Uiso 1 1 calc R U . . .
C41 C 1.0795(3) 0.0377(3) 0.3518(3) 0.1020(12) Uani 1 1 d . . . . .
H41 H 1.108286 0.017962 0.318059 0.122 Uiso 1 1 calc R U . . .
C42 C 0.9782(3) 0.0385(2) 0.3224(2) 0.0891(11) Uani 1 1 d . . . . .
H42 H 0.941618 0.017761 0.269213 0.107 Uiso 1 1 calc R U . . .
H2D H 0.576(2) 0.4105(15) 0.5261(18) 0.062(8) Uiso 1 1 d . . . . .
H6D H 0.8196(19) 0.1007(15) 0.4073(16) 0.047(7) Uiso 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 '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
C5 N1 C7 109.68(19) . . ?
C9 N1 C5 123.8(2) . . ?
C9 N1 C7 126.5(2) . . ?
C12 N2 C13 129.3(2) . . ?
C12 N2 H2D 113.4(19) . . ?
C13 N2 H2D 116.8(18) . . ?
C19 N3 C18 117.7(2) . . ?
C26 N4 C30 109.21(19) . . ?
C28 N4 C26 124.3(2) . . ?
C28 N4 C30 126.5(2) . . ?
C33 N5 C34 129.9(2) . . ?
C33 N5 H6D 116.3(19) . . ?
C34 N5 H6D 113.3(19) . . ?
C42 N6 C39 117.5(3) . . ?
C2 C1 Cl2 119.1(2) . . ?
C2 C1 C6 121.9(2) . . ?
C6 C1 Cl2 119.0(2) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.9(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 C8 129.8(2) . . ?
C5 C4 C8 111.4(2) . . ?
C4 C5 N1 108.9(2) . . ?
C6 C5 N1 128.9(2) . . ?
C6 C5 C4 122.1(2) . . ?
C1 C6 C5 117.1(2) . . ?
C1 C6 H6 121.4 . . ?
C5 C6 H6 121.4 . . ?
N1 C7 H7A 110.7 . . ?
N1 C7 H7B 110.7 . . ?
N1 C7 C8 105.3(2) . . ?
H7A C7 H7B 108.8 . . ?
C8 C7 H7A 110.7 . . ?
C8 C7 H7B 110.7 . . ?
C4 C8 C7 102.6(2) . . ?
C4 C8 H8 109.0 . . ?
C7 C8 H8 109.0 . . ?
C11 C8 C4 112.8(2) . . ?
C11 C8 C7 114.4(2) . . ?
C11 C8 H8 109.0 . . ?
O2 C9 N1 125.4(3) . . ?
O2 C9 C10 118.2(2) . . ?
N1 C9 C10 116.4(3) . . ?
F1 C10 F3 106.4(3) . . ?
F1 C10 C9 112.5(2) . . ?
F2 C10 F1 107.7(3) . . ?
F2 C10 F3 107.1(3) . . ?
F2 C10 C9 109.7(3) . . ?
F3 C10 C9 113.2(2) . . ?
C8 C11 H11A 108.6 . . ?
C8 C11 H11B 108.6 . . ?
C8 C11 C12 114.5(2) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
O1 C12 N2 123.7(3) . . ?
O1 C12 C11 123.0(3) . . ?
N2 C12 C11 113.3(2) . . ?
N2 C13 C18 115.3(2) . . ?
C14 C13 N2 125.2(3) . . ?
C14 C13 C18 119.4(3) . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.7(3) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.0 . . ?
C16 C15 C14 122.1(3) . . ?
C16 C15 H15 119.0 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 119.3(3) . . ?
C16 C17 C21 124.3(3) . . ?
C21 C17 C18 116.5(3) . . ?
N3 C18 C13 117.4(2) . . ?
N3 C18 C17 122.9(3) . . ?
C17 C18 C13 119.7(2) . . ?
N3 C19 H19 118.2 . . ?
N3 C19 C20 123.5(3) . . ?
C20 C19 H19 118.2 . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 119.1(3) . . ?
C21 C20 H20 120.5 . . ?
C17 C21 H21 119.8 . . ?
C20 C21 C17 120.3(3) . . ?
C20 C21 H21 119.8 . . ?
C23 C22 Cl1 119.7(2) . . ?
C23 C22 C27 122.7(3) . . ?
C27 C22 Cl1 117.6(2) . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.5(2) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.7(3) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C31 129.4(2) . . ?
C26 C25 C24 119.2(2) . . ?
C26 C25 C31 111.4(2) . . ?
C25 C26 N4 109.1(2) . . ?
C25 C26 C27 122.5(2) . . ?
C27 C26 N4 128.4(2) . . ?
C22 C27 C26 116.3(2) . . ?
C22 C27 H27 121.8 . . ?
C26 C27 H27 121.8 . . ?
O4 C28 N4 125.4(2) . . ?
O4 C28 C29 117.2(2) . . ?
N4 C28 C29 117.4(2) . . ?
F4 C29 F5 106.8(3) . . ?
F4 C29 F6 107.6(3) . . ?
F4 C29 C28 110.7(3) . . ?
F5 C29 C28 111.9(3) . . ?
F6 C29 F5 104.3(3) . . ?
F6 C29 C28 115.0(2) . . ?
N4 C30 H30A 110.6 . . ?
N4 C30 H30B 110.6 . . ?
N4 C30 C31 105.51(19) . . ?
H30A C30 H30B 108.8 . . ?
C31 C30 H30A 110.6 . . ?
C31 C30 H30B 110.6 . . ?
C25 C31 C30 103.0(2) . . ?
C25 C31 H31 109.1 . . ?
C25 C31 C32 112.8(2) . . ?
C30 C31 H31 109.1 . . ?
C32 C31 C30 113.4(2) . . ?
C32 C31 H31 109.1 . . ?
C31 C32 H32A 109.0 . . ?
C31 C32 H32B 109.0 . . ?
C31 C32 C33 112.8(2) . . ?
H32A C32 H32B 107.8 . . ?
C33 C32 H32A 109.0 . . ?
C33 C32 H32B 109.0 . . ?
O3 C33 N5 123.6(3) . . ?
O3 C33 C32 121.5(2) . . ?
N5 C33 C32 114.9(2) . . ?
N5 C34 C39 115.0(2) . . ?
C35 C34 N5 125.2(3) . . ?
C35 C34 C39 119.8(3) . . ?
C34 C35 H35 120.3 . . ?
C34 C35 C36 119.5(3) . . ?
C36 C35 H35 120.3 . . ?
C35 C36 H36 119.1 . . ?
C37 C36 C35 121.7(3) . . ?
C37 C36 H36 119.1 . . ?
C36 C37 H37 119.8 . . ?
C36 C37 C38 120.3(3) . . ?
C38 C37 H37 119.8 . . ?
C37 C38 C39 119.1(3) . . ?
C40 C38 C37 123.7(3) . . ?
C40 C38 C39 117.3(3) . . ?
N6 C39 C34 117.4(2) . . ?
N6 C39 C38 123.0(3) . . ?
C38 C39 C34 119.6(3) . . ?
C38 C40 H40 120.2 . . ?
C41 C40 C38 119.7(3) . . ?
C41 C40 H40 120.2 . . ?
C40 C41 H41 120.4 . . ?
C40 C41 C42 119.3(3) . . ?
C42 C41 H41 120.4 . . ?
N6 C42 C41 123.2(3) . . ?
N6 C42 H42 118.4 . . ?
C41 C42 H42 118.4 . . ?
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
Cl1 C22 1.740(3) . ?
Cl2 C1 1.736(3) . ?
F1 C10 1.322(3) . ?
F2 C10 1.316(3) . ?
F3 C10 1.323(4) . ?
F4 C29 1.291(3) . ?
F5 C29 1.319(4) . ?
F6 C29 1.306(3) . ?
O1 C12 1.206(3) . ?
O2 C9 1.206(3) . ?
O3 C33 1.219(3) . ?
O4 C28 1.211(3) . ?
N1 C5 1.419(3) . ?
N1 C7 1.483(3) . ?
N1 C9 1.348(3) . ?
N2 C12 1.348(3) . ?
N2 C13 1.402(3) . ?
N2 H2D 0.91(3) . ?
N3 C18 1.360(3) . ?
N3 C19 1.322(4) . ?
N4 C26 1.424(3) . ?
N4 C28 1.339(3) . ?
N4 C30 1.479(3) . ?
N5 C33 1.332(3) . ?
N5 C34 1.398(3) . ?
N5 H6D 0.80(3) . ?
N6 C39 1.360(3) . ?
N6 C42 1.311(4) . ?
C1 C2 1.372(4) . ?
C1 C6 1.379(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(4) . ?
C4 C5 1.387(3) . ?
C4 C8 1.510(4) . ?
C5 C6 1.381(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.534(4) . ?
C8 H8 0.9800 . ?
C8 C11 1.496(4) . ?
C9 C10 1.530(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.518(4) . ?
C13 C14 1.362(4) . ?
C13 C18 1.418(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.409(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.345(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.395(4) . ?
C17 C18 1.413(4) . ?
C17 C21 1.412(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.350(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(4) . ?
C22 C27 1.386(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.379(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.389(3) . ?
C25 C26 1.378(3) . ?
C25 C31 1.502(3) . ?
C26 C27 1.387(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.520(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.526(3) . ?
C31 H31 0.9800 . ?
C31 C32 1.516(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.518(4) . ?
C34 C35 1.366(4) . ?
C34 C39 1.420(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.410(4) . ?
C36 H36 0.9300 . ?
C36 C37 1.348(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.400(5) . ?
C38 C39 1.409(4) . ?
C38 C40 1.400(5) . ?
C40 H40 0.9300 . ?
C40 C41 1.350(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.414(5) . ?
C42 H42 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
Cl1 C22 C23 C24 179.2(2) . . . . ?
Cl1 C22 C27 C26 -178.64(18) . . . . ?
Cl2 C1 C2 C3 177.8(2) . . . . ?
Cl2 C1 C6 C5 -178.71(18) . . . . ?
O2 C9 C10 F1 -111.8(3) . . . . ?
O2 C9 C10 F2 8.0(4) . . . . ?
O2 C9 C10 F3 127.5(3) . . . . ?
O4 C28 C29 F4 -8.0(5) . . . . ?
O4 C28 C29 F5 111.0(3) . . . . ?
O4 C28 C29 F6 -130.2(3) . . . . ?
N1 C5 C6 C1 -179.5(2) . . . . ?
N1 C7 C8 C4 -14.1(3) . . . . ?
N1 C7 C8 C11 -136.5(2) . . . . ?
N1 C9 C10 F1 66.9(3) . . . . ?
N1 C9 C10 F2 -173.2(3) . . . . ?
N1 C9 C10 F3 -53.7(4) . . . . ?
N2 C13 C14 C15 177.9(3) . . . . ?
N2 C13 C18 N3 2.2(3) . . . . ?
N2 C13 C18 C17 -177.7(2) . . . . ?
N3 C19 C20 C21 0.0(5) . . . . ?
N4 C26 C27 C22 177.8(2) . . . . ?
N4 C28 C29 F4 172.5(3) . . . . ?
N4 C28 C29 F5 -68.5(4) . . . . ?
N4 C28 C29 F6 50.3(4) . . . . ?
N4 C30 C31 C25 12.6(3) . . . . ?
N4 C30 C31 C32 -109.6(2) . . . . ?
N5 C34 C35 C36 178.0(3) . . . . ?
N5 C34 C39 N6 0.8(4) . . . . ?
N5 C34 C39 C38 -178.6(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C2 C3 C4 C8 -177.4(3) . . . . ?
C3 C4 C5 N1 178.4(2) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C3 C4 C8 C7 -170.6(3) . . . . ?
C3 C4 C8 C11 -47.0(4) . . . . ?
C4 C5 C6 C1 1.3(4) . . . . ?
C4 C8 C11 C12 -175.4(2) . . . . ?
C5 N1 C7 C8 13.5(3) . . . . ?
C5 N1 C9 O2 -0.5(4) . . . . ?
C5 N1 C9 C10 -179.1(2) . . . . ?
C5 C4 C8 C7 10.7(3) . . . . ?
C5 C4 C8 C11 134.2(2) . . . . ?
C6 C1 C2 C3 -1.6(4) . . . . ?
C7 N1 C5 C4 -7.0(3) . . . . ?
C7 N1 C5 C6 173.6(2) . . . . ?
C7 N1 C9 O2 179.5(3) . . . . ?
C7 N1 C9 C10 0.9(4) . . . . ?
C7 C8 C11 C12 -58.7(3) . . . . ?
C8 C4 C5 N1 -2.7(3) . . . . ?
C8 C4 C5 C6 176.7(2) . . . . ?
C8 C11 C12 O1 4.0(4) . . . . ?
C8 C11 C12 N2 -178.3(2) . . . . ?
C9 N1 C5 C4 173.0(2) . . . . ?
C9 N1 C5 C6 -6.4(4) . . . . ?
C9 N1 C7 C8 -166.5(2) . . . . ?
C12 N2 C13 C14 -13.2(4) . . . . ?
C12 N2 C13 C18 166.3(2) . . . . ?
C13 N2 C12 O1 7.2(4) . . . . ?
C13 N2 C12 C11 -170.5(2) . . . . ?
C13 C14 C15 C16 0.7(5) . . . . ?
C14 C13 C18 N3 -178.4(2) . . . . ?
C14 C13 C18 C17 1.7(4) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C15 C16 C17 C21 -179.7(3) . . . . ?
C16 C17 C18 N3 179.0(2) . . . . ?
C16 C17 C18 C13 -1.1(4) . . . . ?
C16 C17 C21 C20 -178.2(3) . . . . ?
C18 N3 C19 C20 0.7(5) . . . . ?
C18 C13 C14 C15 -1.5(4) . . . . ?
C18 C17 C21 C20 1.8(4) . . . . ?
C19 N3 C18 C13 179.9(2) . . . . ?
C19 N3 C18 C17 -0.2(4) . . . . ?
C19 C20 C21 C17 -1.3(5) . . . . ?
C21 C17 C18 N3 -1.0(4) . . . . ?
C21 C17 C18 C13 178.9(2) . . . . ?
C22 C23 C24 C25 -1.3(4) . . . . ?
C23 C22 C27 C26 -0.6(4) . . . . ?
C23 C24 C25 C26 0.8(4) . . . . ?
C23 C24 C25 C31 -178.4(3) . . . . ?
C24 C25 C26 N4 -178.3(2) . . . . ?
C24 C25 C26 C27 -0.2(4) . . . . ?
C24 C25 C31 C30 170.5(3) . . . . ?
C24 C25 C31 C32 -66.9(3) . . . . ?
C25 C26 C27 C22 0.1(4) . . . . ?
C25 C31 C32 C33 171.5(2) . . . . ?
C26 N4 C28 O4 3.2(5) . . . . ?
C26 N4 C28 C29 -177.4(2) . . . . ?
C26 N4 C30 C31 -12.8(3) . . . . ?
C26 C25 C31 C30 -8.8(3) . . . . ?
C26 C25 C31 C32 113.8(2) . . . . ?
C27 C22 C23 C24 1.3(4) . . . . ?
C28 N4 C26 C25 -171.3(2) . . . . ?
C28 N4 C26 C27 10.8(4) . . . . ?
C28 N4 C30 C31 166.0(2) . . . . ?
C30 N4 C26 C25 7.6(3) . . . . ?
C30 N4 C26 C27 -170.3(2) . . . . ?
C30 N4 C28 O4 -175.5(3) . . . . ?
C30 N4 C28 C29 3.9(4) . . . . ?
C30 C31 C32 C33 -71.9(3) . . . . ?
C31 C25 C26 N4 1.1(3) . . . . ?
C31 C25 C26 C27 179.2(2) . . . . ?
C31 C32 C33 O3 15.0(4) . . . . ?
C31 C32 C33 N5 -164.6(2) . . . . ?
C33 N5 C34 C35 12.2(5) . . . . ?
C33 N5 C34 C39 -168.6(3) . . . . ?
C34 N5 C33 O3 -1.1(5) . . . . ?
C34 N5 C33 C32 178.5(3) . . . . ?
C34 C35 C36 C37 1.2(5) . . . . ?
C35 C34 C39 N6 -179.9(3) . . . . ?
C35 C34 C39 C38 0.7(4) . . . . ?
C35 C36 C37 C38 -0.7(6) . . . . ?
C36 C37 C38 C39 0.2(5) . . . . ?
C36 C37 C38 C40 -179.9(3) . . . . ?
C37 C38 C39 N6 -179.6(3) . . . . ?
C37 C38 C39 C34 -0.2(4) . . . . ?
C37 C38 C40 C41 -179.1(4) . . . . ?
C38 C40 C41 C42 -1.7(6) . . . . ?
C39 N6 C42 C41 -0.2(5) . . . . ?
C39 C34 C35 C36 -1.1(4) . . . . ?
C39 C38 C40 C41 0.7(5) . . . . ?
C40 C38 C39 N6 0.6(4) . . . . ?
C40 C38 C39 C34 179.9(3) . . . . ?
C40 C41 C42 N6 1.4(7) . . . . ?
C42 N6 C39 C34 179.8(3) . . . . ?
C42 N6 C39 C38 -0.8(4) . . . . ?
