#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:31:16 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268574 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/85/7128581.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_7128581
loop_
_publ_author_name
'Hu, Xiao'
'Ding, Aishun'
'Xu, Dawen'
'Guo, Hao'
_publ_section_title
;
 Visible light-induced one-pot synthesis of
 CF₃/CF₂-substituted cyclobutene derivatives.
;
_journal_issue                   60
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7441
_journal_page_last               7444
_journal_paper_doi               10.1039/d1cc02696h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C19 H13 F2 N O'
_chemical_formula_weight         309.30
_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   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-04-08 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                112.81(3)
_cell_angle_beta                 107.33(3)
_cell_angle_gamma                96.28(3)
_cell_formula_units_Z            4
_cell_length_a                   8.982(5)
_cell_length_b                   13.786(5)
_cell_length_c                   13.975(3)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      56.99
_cell_measurement_theta_min      3.14
_cell_volume                     1472.2(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            44799
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.499
_diffrn_reflns_theta_min         3.349
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0116(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         5927
_refine_ls_number_restraints     76
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0447
_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/[σ²(Fo²)+(0.0629P)²+0.3470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1250
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4918
_reflns_number_total             5927
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02696h2.cif
_cod_data_source_block           210330a_0m_a
_cod_depositor_comments
'Adding full bibliography for 7128581--7128583.cif.'
_cod_original_cell_volume        1472.2(11)
_cod_database_code               7128581
_shelx_shelxl_version_number     2016/6
_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_min   0.699
_shelx_estimated_absorpt_t_max   0.927
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 0.16384(14) 0.16502(9) 0.77589(10) 0.0614(3) Uani 1 1 d . . . . .
F2 F -0.00817(13) 0.13458(9) 0.61455(10) 0.0619(3) Uani 1 1 d . . . . .
N1 N 0.63028(14) 0.51554(10) 0.80362(10) 0.0306(3) Uani 1 1 d . . . . .
O1 O 0.49650(13) 0.51714(9) 0.63604(9) 0.0396(3) Uani 1 1 d . . . . .
C1 C 0.49751(17) 0.47895(11) 0.70233(12) 0.0309(3) Uani 1 1 d . . . . .
C2 C 0.37299(17) 0.39480(11) 0.68906(12) 0.0301(3) Uani 1 1 d . . . . .
C3 C 0.20673(17) 0.32091(12) 0.60640(13) 0.0347(3) Uani 1 1 d . . . . .
H3A H 0.204532 0.269380 0.532853 0.042 Uiso 1 1 calc R U . . .
H3B H 0.119556 0.358780 0.598611 0.042 Uiso 1 1 calc R U . . .
C4 C 0.22511(18) 0.27484(12) 0.69234(12) 0.0337(3) Uani 1 1 d . . . . .
C5 C 0.38276(17) 0.35359(11) 0.76343(12) 0.0294(3) Uani 1 1 d . . . . .
C6 C 0.51693(17) 0.39133(11) 0.86618(12) 0.0301(3) Uani 1 1 d . . . . .
C7 C 0.53071(19) 0.35198(13) 0.94613(12) 0.0358(3) Uani 1 1 d . . . . .
H7 H 0.446315 0.295116 0.933412 0.043 Uiso 1 1 calc R U . . .
C8 C 0.6657(2) 0.39506(14) 1.04314(13) 0.0413(4) Uani 1 1 d . . . . .
H8 H 0.675646 0.367301 1.096619 0.050 Uiso 1 1 calc R U . . .
C9 C 0.7876(2) 0.47978(14) 1.06191(13) 0.0422(4) Uani 1 1 d . . . . .
H9 H 0.879846 0.510310 1.129303 0.051 Uiso 1 1 calc R U . . .
C10 C 0.77693(18) 0.52023(13) 0.98461(13) 0.0378(3) Uani 1 1 d . . . . .
H10 H 0.861634 0.578061 0.999458 0.045 Uiso 1 1 calc R U . . .
C11 C 0.64205(17) 0.47671(11) 0.88419(12) 0.0307(3) Uani 1 1 d . . . . .
C12 C 0.76495(18) 0.60003(13) 0.82103(13) 0.0371(3) Uani 1 1 d . . . . .
H12A H 0.761298 0.593722 0.747300 0.045 Uiso 1 1 calc R U . . .
H12B H 0.867989 0.586527 0.857377 0.045 Uiso 1 1 calc R U . . .
C13 C 0.7623(2) 0.71470(13) 0.89180(13) 0.0390(4) Uani 1 1 d . . . . .
C14 C 0.6201(2) 0.74801(14) 0.87498(15) 0.0466(4) Uani 1 1 d . . . . .
H14 H 0.521509 0.696686 0.821436 0.056 Uiso 1 1 calc R U . . .
C15 C 0.6199(3) 0.85503(16) 0.93513(18) 0.0656(6) Uani 1 1 d . . . . .
H15 H 0.521707 0.876659 0.922972 0.079 Uiso 1 1 calc R U . . .
C16 C 0.7623(4) 0.92964(18) 1.01243(19) 0.0788(7) Uani 1 1 d . U . . .
H16 H 0.762398 1.003062 1.053416 0.095 Uiso 1 1 calc R U . . .
C17 C 0.9046(3) 0.89873(17) 1.03081(16) 0.0749(7) Uani 1 1 d . U . . .
H17 H 1.002463 0.950746 1.084586 0.090 Uiso 1 1 calc R U . . .
C18 C 0.9057(2) 0.79073(15) 0.97044(14) 0.0533(5) Uani 1 1 d . . . . .
H18 H 1.004122 0.769494 0.983206 0.064 Uiso 1 1 calc R U . . .
C19 C 0.1335(2) 0.19607(14) 0.69489(14) 0.0428(4) Uani 1 1 d . . . . .
N2 N 0.66690(14) 0.30969(10) 0.55316(10) 0.0300(3) Uani 1 1 d . . . . .
O2 O 0.90745(13) 0.39099(9) 0.70377(9) 0.0437(3) Uani 1 1 d . . . . .
C20 C 0.77655(17) 0.32232(12) 0.65480(12) 0.0325(3) Uani 1 1 d . . . . .
C21 C 0.71729(19) 0.24871(13) 0.69266(12) 0.0355(3) Uani 1 1 d . . . . .
C22 C 0.7633(2) 0.22077(15) 0.79095(14) 0.0469(4) Uani 1 1 d . . . . .
H22A H 0.775328 0.280308 0.863329 0.056 Uiso 1 1 calc R U . . .
H22B H 0.854657 0.186439 0.797960 0.056 Uiso 1 1 calc R U . . .
C23 C 0.5958(2) 0.14040(14) 0.72598(15) 0.0448(4) Uani 1 1 d D . . . .
C24 C 0.57254(19) 0.17501(12) 0.63645(13) 0.0347(3) Uani 1 1 d . . . . .
C25 C 0.46426(18) 0.15871(12) 0.53037(12) 0.0331(3) Uani 1 1 d . . . . .
C26 C 0.3161(2) 0.08032(13) 0.46571(14) 0.0414(4) Uani 1 1 d . . . . .
H26 H 0.279931 0.032461 0.492721 0.050 Uiso 1 1 calc R U . . .
C27 C 0.2228(2) 0.07201(14) 0.36395(15) 0.0470(4) Uani 1 1 d . . . . .
H27 H 0.122670 0.018684 0.320537 0.056 Uiso 1 1 calc R U . . .
C28 C 0.2765(2) 0.14264(15) 0.32471(14) 0.0456(4) Uani 1 1 d . . . . .
H28 H 0.212193 0.136280 0.253857 0.055 Uiso 1 1 calc R U . . .
C29 C 0.42037(18) 0.22127(14) 0.38638(13) 0.0383(3) Uani 1 1 d . . . . .
H29 H 0.453474 0.269153 0.358453 0.046 Uiso 1 1 calc R U . . .
C30 C 0.51844(17) 0.23087(11) 0.49057(12) 0.0306(3) Uani 1 1 d . . . . .
C31 C 0.71665(18) 0.38469(12) 0.51037(12) 0.0337(3) Uani 1 1 d . . . . .
H31A H 0.798040 0.449943 0.573663 0.040 Uiso 1 1 calc R U . . .
H31B H 0.621916 0.408695 0.478725 0.040 Uiso 1 1 calc R U . . .
C32 C 0.78658(16) 0.33608(12) 0.42184(12) 0.0313(3) Uani 1 1 d . . . . .
C33 C 0.83856(18) 0.40137(13) 0.37705(14) 0.0389(4) Uani 1 1 d . . . . .
H33 H 0.828589 0.474125 0.402318 0.047 Uiso 1 1 calc R U . . .
C34 C 0.9045(2) 0.36183(16) 0.29628(15) 0.0472(4) Uani 1 1 d . . . . .
H34 H 0.940359 0.407489 0.266949 0.057 Uiso 1 1 calc R U . . .
C35 C 0.9181(2) 0.25574(17) 0.25831(15) 0.0521(5) Uani 1 1 d . . . . .
H35 H 0.962141 0.227970 0.202204 0.062 Uiso 1 1 calc R U . . .
C36 C 0.8675(2) 0.19036(15) 0.30239(15) 0.0488(4) Uani 1 1 d . . . . .
H36 H 0.876858 0.117469 0.276513 0.059 Uiso 1 1 calc R U . . .
C37 C 0.80276(19) 0.23055(13) 0.38442(13) 0.0384(3) Uani 1 1 d . . . . .
H37 H 0.769476 0.185258 0.414923 0.046 Uiso 1 1 calc R U . . .
C38 C 0.5005(16) 0.0754(5) 0.7455(7) 0.0549(16) Uani 0.79(4) 1 d . U P A 1
F3 F 0.3506(15) 0.0160(4) 0.6797(8) 0.0710(16) Uani 0.79(4) 1 d . U P A 1
F4 F 0.5449(19) 0.0580(7) 0.8360(8) 0.0828(19) Uani 0.79(4) 1 d . . P A 1
C38' C 0.545(3) 0.0756(18) 0.7605(18) 0.048(4) Uani 0.21(4) 1 d D U P A 2
F3' F 0.401(3) 0.008(2) 0.695(2) 0.072(4) Uani 0.21(4) 1 d D U P A 2
F4' F 0.609(4) 0.076(2) 0.8579(18) 0.068(4) Uani 0.21(4) 1 d D 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 0.0137 0.0067 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
C11 N1 C1 125.22(12) . . ?
C11 N1 C12 119.98(12) . . ?
C1 N1 C12 114.79(12) . . ?
O1 C1 N1 121.28(13) . . ?
O1 C1 C2 126.71(14) . . ?
N1 C1 C2 112.01(13) . . ?
C5 C2 C1 124.15(14) . . ?
C5 C2 C3 95.22(12) . . ?
C1 C2 C3 140.62(13) . . ?
C2 C3 C4 82.87(11) . . ?
C2 C3 H3A 114.8 . . ?
C4 C3 H3A 114.8 . . ?
C2 C3 H3B 114.8 . . ?
C4 C3 H3B 114.8 . . ?
H3A C3 H3B 111.9 . . ?
C19 C4 C5 137.24(15) . . ?
C19 C4 C3 132.75(15) . . ?
C5 C4 C3 90.00(11) . . ?
C2 C5 C6 123.65(13) . . ?
C2 C5 C4 91.89(12) . . ?
C6 C5 C4 144.46(14) . . ?
C7 C6 C11 120.39(14) . . ?
C7 C6 C5 125.42(14) . . ?
C11 C6 C5 114.18(13) . . ?
C8 C7 C6 120.55(15) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 119.27(15) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 121.36(15) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 120.62(15) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 N1 121.46(14) . . ?
C10 C11 C6 117.79(14) . . ?
N1 C11 C6 120.75(13) . . ?
N1 C12 C13 113.71(12) . . ?
N1 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N1 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C18 118.84(17) . . ?
C14 C13 C12 121.18(15) . . ?
C18 C13 C12 119.85(17) . . ?
C15 C14 C13 121.02(19) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 119.8(2) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C4 C19 F1 126.56(16) . . ?
C4 C19 F2 124.15(16) . . ?
F1 C19 F2 109.28(14) . . ?
C20 N2 C30 124.90(13) . . ?
C20 N2 C31 115.69(13) . . ?
C30 N2 C31 119.40(12) . . ?
O2 C20 N2 121.64(14) . . ?
O2 C20 C21 126.00(14) . . ?
N2 C20 C21 112.35(13) . . ?
C24 C21 C20 124.00(14) . . ?
C24 C21 C22 95.07(14) . . ?
C20 C21 C22 140.89(16) . . ?
C21 C22 C23 83.27(13) . . ?
C21 C22 H22A 114.8 . . ?
C23 C22 H22A 114.8 . . ?
C21 C22 H22B 114.8 . . ?
C23 C22 H22B 114.8 . . ?
H22A C22 H22B 111.8 . . ?
C38' C23 C24 148.5(10) . . ?
C38 C23 C24 133.7(6) . . ?
C38' C23 C22 121.5(10) . . ?
C38 C23 C22 136.2(5) . . ?
C24 C23 C22 89.70(13) . . ?
C21 C24 C25 123.56(14) . . ?
C21 C24 C23 91.93(14) . . ?
C25 C24 C23 144.51(16) . . ?
C26 C25 C30 119.83(14) . . ?
C26 C25 C24 126.20(15) . . ?
C30 C25 C24 113.97(14) . . ?
C27 C26 C25 120.73(16) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 119.40(16) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C29 C28 C27 121.47(16) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C30 120.14(16) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 N2 120.49(13) . . ?
C29 C30 C25 118.42(14) . . ?
N2 C30 C25 121.08(13) . . ?
N2 C31 C32 114.05(12) . . ?
N2 C31 H31A 108.7 . . ?
C32 C31 H31A 108.7 . . ?
N2 C31 H31B 108.7 . . ?
C32 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
C37 C32 C33 118.71(14) . . ?
C37 C32 C31 123.08(13) . . ?
C33 C32 C31 118.21(13) . . ?
C34 C33 C32 120.95(15) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C35 C34 C33 119.90(15) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C36 C35 C34 119.65(16) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C35 C36 C37 120.41(17) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C32 C37 C36 120.38(15) . . ?
C32 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
F3 C38 F4 108.8(5) . . ?
F3 C38 C23 127.2(6) . . ?
F4 C38 C23 124.0(6) . . ?
C23 C38' F4' 127.9(18) . . ?
C23 C38' F3' 115.6(17) . . ?
F4' C38' F3' 116.0(18) . . ?
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 C19 1.325(2) . ?
F2 C19 1.332(2) . ?
N1 C11 1.4051(19) . ?
N1 C1 1.411(2) . ?
N1 C12 1.475(2) . ?
O1 C1 1.2287(17) . ?
C1 C2 1.434(2) . ?
C2 C5 1.351(2) . ?
C2 C3 1.526(2) . ?
C3 C4 1.539(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C19 1.307(2) . ?
C4 C5 1.470(2) . ?
C5 C6 1.427(2) . ?
C6 C7 1.400(2) . ?
C6 C11 1.423(2) . ?
C7 C8 1.379(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.404(2) . ?
C10 H10 0.9500 . ?
C12 C13 1.512(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.390(3) . ?
C13 C18 1.390(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.401(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N2 C20 1.3984(19) . ?
N2 C30 1.405(2) . ?
N2 C31 1.4709(18) . ?
O2 C20 1.234(2) . ?
C20 C21 1.435(2) . ?
C21 C24 1.350(2) . ?
C21 C22 1.521(2) . ?
C22 C23 1.535(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C38' 1.270(16) . ?
C23 C38 1.331(7) . ?
C23 C24 1.472(2) . ?
C24 C25 1.424(2) . ?
C25 C26 1.403(2) . ?
C25 C30 1.421(2) . ?
C26 C27 1.371(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.396(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.376(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.405(2) . ?
C29 H29 0.9500 . ?
C31 C32 1.512(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C37 1.383(2) . ?
C32 C33 1.393(2) . ?
C33 C34 1.383(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.381(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.390(2) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 F3 1.329(7) . ?
C38 F4 1.330(6) . ?
C38' F4' 1.304(17) . ?
C38' F3' 1.321(18) . ?
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
C11 N1 C1 O1 -179.97(13) . . . . ?
C12 N1 C1 O1 -1.01(19) . . . . ?
C11 N1 C1 C2 -0.66(19) . . . . ?
C12 N1 C1 C2 178.30(12) . . . . ?
O1 C1 C2 C5 177.91(14) . . . . ?
N1 C1 C2 C5 -1.36(19) . . . . ?
O1 C1 C2 C3 -0.2(3) . . . . ?
N1 C1 C2 C3 -179.43(16) . . . . ?
C5 C2 C3 C4 -1.21(11) . . . . ?
C1 C2 C3 C4 177.19(18) . . . . ?
C2 C3 C4 C19 -178.01(18) . . . . ?
C2 C3 C4 C5 1.11(10) . . . . ?
C1 C2 C5 C6 1.9(2) . . . . ?
C3 C2 C5 C6 -179.30(13) . . . . ?
C1 C2 C5 C4 -177.52(13) . . . . ?
C3 C2 C5 C4 1.26(11) . . . . ?
C19 C4 C5 C2 177.8(2) . . . . ?
C3 C4 C5 C2 -1.24(11) . . . . ?
C19 C4 C5 C6 -1.4(3) . . . . ?
C3 C4 C5 C6 179.56(19) . . . . ?
C2 C5 C6 C7 179.02(14) . . . . ?
C4 C5 C6 C7 -1.9(3) . . . . ?
C2 C5 C6 C11 -0.4(2) . . . . ?
C4 C5 C6 C11 178.68(18) . . . . ?
C11 C6 C7 C8 -0.2(2) . . . . ?
C5 C6 C7 C8 -179.55(14) . . . . ?
C6 C7 C8 C9 1.1(2) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 N1 -178.90(13) . . . . ?
C9 C10 C11 C6 1.0(2) . . . . ?
C1 N1 C11 C10 -177.98(13) . . . . ?
C12 N1 C11 C10 3.1(2) . . . . ?
C1 N1 C11 C6 2.2(2) . . . . ?
C12 N1 C11 C6 -176.75(12) . . . . ?
C7 C6 C11 C10 -0.8(2) . . . . ?
C5 C6 C11 C10 178.58(12) . . . . ?
C7 C6 C11 N1 179.02(12) . . . . ?
C5 C6 C11 N1 -1.56(18) . . . . ?
C11 N1 C12 C13 -84.42(17) . . . . ?
C1 N1 C12 C13 96.56(15) . . . . ?
N1 C12 C13 C14 -44.2(2) . . . . ?
N1 C12 C13 C18 140.04(15) . . . . ?
C18 C13 C14 C15 0.0(2) . . . . ?
C12 C13 C14 C15 -175.85(16) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C14 C13 C18 C17 -0.1(2) . . . . ?
C12 C13 C18 C17 175.82(15) . . . . ?
C16 C17 C18 C13 0.0(3) . . . . ?
C5 C4 C19 F1 1.9(3) . . . . ?
C3 C4 C19 F1 -179.38(15) . . . . ?
C5 C4 C19 F2 -178.74(16) . . . . ?
C3 C4 C19 F2 0.0(3) . . . . ?
C30 N2 C20 O2 177.57(13) . . . . ?
C31 N2 C20 O2 -1.18(19) . . . . ?
C30 N2 C20 C21 -3.10(19) . . . . ?
C31 N2 C20 C21 178.16(11) . . . . ?
O2 C20 C21 C24 179.68(14) . . . . ?
N2 C20 C21 C24 0.4(2) . . . . ?
O2 C20 C21 C22 2.6(3) . . . . ?
N2 C20 C21 C22 -176.71(17) . . . . ?
C24 C21 C22 C23 -1.57(12) . . . . ?
C20 C21 C22 C23 176.01(19) . . . . ?
C21 C22 C23 C38' 176.9(15) . . . . ?
C21 C22 C23 C38 -171.6(6) . . . . ?
C21 C22 C23 C24 1.43(11) . . . . ?
C20 C21 C24 C25 2.7(2) . . . . ?
C22 C21 C24 C25 -179.17(13) . . . . ?
C20 C21 C24 C23 -176.53(14) . . . . ?
C22 C21 C24 C23 1.62(12) . . . . ?
C38' C23 C24 C21 -174(2) . . . . ?
C38 C23 C24 C21 171.7(5) . . . . ?
C22 C23 C24 C21 -1.60(12) . . . . ?
C38' C23 C24 C25 7(2) . . . . ?
C38 C23 C24 C25 -7.2(6) . . . . ?
C22 C23 C24 C25 179.5(2) . . . . ?
C21 C24 C25 C26 176.87(14) . . . . ?
C23 C24 C25 C26 -4.5(3) . . . . ?
C21 C24 C25 C30 -2.9(2) . . . . ?
C23 C24 C25 C30 175.74(19) . . . . ?
C30 C25 C26 C27 0.3(2) . . . . ?
C24 C25 C26 C27 -179.41(14) . . . . ?
C25 C26 C27 C28 -0.1(2) . . . . ?
C26 C27 C28 C29 -0.6(3) . . . . ?
C27 C28 C29 C30 1.0(2) . . . . ?
C28 C29 C30 N2 178.87(14) . . . . ?
C28 C29 C30 C25 -0.7(2) . . . . ?
C20 N2 C30 C29 -176.71(13) . . . . ?
C31 N2 C30 C29 1.99(19) . . . . ?
C20 N2 C30 C25 2.9(2) . . . . ?
C31 N2 C30 C25 -178.42(12) . . . . ?
C26 C25 C30 C29 0.1(2) . . . . ?
C24 C25 C30 C29 179.84(13) . . . . ?
C26 C25 C30 N2 -179.53(13) . . . . ?
C24 C25 C30 N2 0.24(19) . . . . ?
C20 N2 C31 C32 98.99(15) . . . . ?
C30 N2 C31 C32 -79.82(16) . . . . ?
N2 C31 C32 C37 -0.1(2) . . . . ?
N2 C31 C32 C33 -179.40(13) . . . . ?
C37 C32 C33 C34 0.3(2) . . . . ?
C31 C32 C33 C34 179.62(14) . . . . ?
C32 C33 C34 C35 0.6(2) . . . . ?
C33 C34 C35 C36 -0.8(3) . . . . ?
C34 C35 C36 C37 0.1(3) . . . . ?
C33 C32 C37 C36 -1.0(2) . . . . ?
C31 C32 C37 C36 179.74(15) . . . . ?
C35 C36 C37 C32 0.8(3) . . . . ?
C24 C23 C38 F3 4.4(9) . . . . ?
C22 C23 C38 F3 174.8(4) . . . . ?
C24 C23 C38 F4 -177.3(5) . . . . ?
C22 C23 C38 F4 -7.0(11) . . . . ?
C24 C23 C38' F4' -177.6(15) . . . . ?
C22 C23 C38' F4' 11(3) . . . . ?
C24 C23 C38' F3' -7(4) . . . . ?
C22 C23 C38' F3' -177.9(16) . . . . ?
