#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:22:04 +0300 (Fri, 05 May 2023) $
#$Revision: 283470 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159255.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_7159255
loop_
_publ_author_name
'Sierra, Sonia'
'López, Rosa'
'Gómez-Bengoa, Enrique'
'Falvello, Larry R.'
'Urriolabeitia, Esteban P.'
_publ_section_title
;
 Synthesis of 1,2-diaminotruxinic δ-cyclobutanes by
 BF₃-controlled [2 + 2]-photocycloaddition of
 5(4H)-oxazolones and stereoselective expansion of
 δ-cyclobutanes to give highly substituted
 pyrrolidine-2,5-dicarboxylates.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3203
_journal_page_last               3213
_journal_paper_doi               10.1039/d3ob00284e
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C34 H28 F2 N2 O6,C H2 Cl2'
_chemical_formula_sum            'C35 H30 Cl2 F2 N2 O6'
_chemical_formula_weight         683.51
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2022-06-06 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                96.5540(10)
_cell_angle_beta                 96.0450(10)
_cell_angle_gamma                105.3120(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6404(8)
_cell_length_b                   10.1481(9)
_cell_length_c                   17.4357(15)
_cell_measurement_reflns_used    5247
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.815
_cell_measurement_theta_min      2.212
_cell_volume                     1618.0(2)
_computing_cell_refinement       'SAINT+ in APEX3 v. 2017.3 (Bruker AXS, 2008)'
_computing_data_collection       'SMART in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT+ in APEX3 v. 2017.3 (Bruker AXS, 2008)'
_computing_molecular_graphics    'ORTEP-3 (farrugia, 2012)'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_device_type  'Bruker APEX CCD system'
_diffrn_measurement_method       'narrow ω frames'
_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  0.0801
_diffrn_reflns_av_unetI/netI     0.1178
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17405
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         29.381
_diffrn_reflns_theta_min         2.104
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.5939
_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    1.403
_exptl_crystal_description       plate
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         7779
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0851
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1467P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2397
_refine_ls_wR_factor_ref         0.2648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4414
_reflns_number_total             7779
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00284e2.cif
_cod_data_source_block           cmpnd_2o
_cod_depositor_comments
'Adding full bibliography for 7159254--7159256.cif.'
_cod_database_code               7159255
_shelx_shelxl_version_number     2019/2
_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.
;
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 0.7613(2) 0.2015(3) 0.80579(14) 0.0519(7) Uani 1 1 d . . . . .
F2 F 0.0445(2) 0.1811(2) 0.82394(14) 0.0390(5) Uani 1 1 d . . . . .
O4 O 0.2416(2) 0.5074(2) 0.78381(15) 0.0331(6) Uani 1 1 d . . . . .
O5 O 0.0845(2) 0.3401(2) 0.69828(14) 0.0283(5) Uani 1 1 d . . . . .
O6 O 0.2902(3) 0.3812(2) 0.58820(14) 0.0314(5) Uani 1 1 d . . . . .
O1 O 0.5988(3) 0.2891(2) 0.64986(14) 0.0336(6) Uani 1 1 d . . . . .
O2 O 0.5954(3) 0.5118(2) 0.66212(14) 0.0319(5) Uani 1 1 d . . . . .
O3 O 0.7635(2) 0.5359(2) 0.81460(14) 0.0277(5) Uani 1 1 d . . . . .
N2 N 0.2795(3) 0.2121(2) 0.66183(15) 0.0208(5) Uani 1 1 d D . . . .
N1 N 0.5218(3) 0.5100(2) 0.80351(15) 0.0203(5) Uani 1 1 d . . . . .
C1 C 0.5996(3) 0.2846(3) 0.87419(18) 0.0217(6) Uani 1 1 d . . . . .
C2 C 0.7339(4) 0.2609(3) 0.8733(2) 0.0294(7) Uani 1 1 d . . . . .
C3 C 0.8402(4) 0.2968(4) 0.9370(2) 0.0371(9) Uani 1 1 d . . . . .
H3 H 0.931588 0.279479 0.933053 0.044 Uiso 1 1 calc R U . . .
C4 C 0.8138(4) 0.3578(4) 1.0063(2) 0.0377(9) Uani 1 1 d . . . . .
H4 H 0.886793 0.384192 1.050568 0.045 Uiso 1 1 calc R U . . .
C5 C 0.6790(4) 0.3804(4) 1.0106(2) 0.0346(8) Uani 1 1 d . . . . .
H5 H 0.658796 0.421479 1.058324 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5736(4) 0.3432(4) 0.9456(2) 0.0309(7) Uani 1 1 d . . . . .
H6 H 0.481228 0.357901 0.949798 0.037 Uiso 1 1 calc R U . . .
C7 C 0.4879(3) 0.3783(3) 0.75375(18) 0.0194(6) Uani 1 1 d . . . . .
C8 C 0.4946(3) 0.2553(3) 0.80016(17) 0.0191(6) Uani 1 1 d . . . . .
H8 H 0.510203 0.177699 0.764473 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5692(3) 0.3869(3) 0.68338(18) 0.0226(6) Uani 1 1 d . . . . .
C10 C 0.6625(5) 0.5264(5) 0.5927(3) 0.0521(11) Uani 1 1 d . . . . .
H10A H 0.753806 0.500852 0.599222 0.078 Uiso 1 1 calc R U . . .
H10B H 0.682497 0.622482 0.583159 0.078 Uiso 1 1 calc R U . . .
H10C H 0.597073 0.465727 0.548219 0.078 Uiso 1 1 calc R U . . .
C11 C 0.6611(3) 0.5792(3) 0.83116(18) 0.0217(6) Uani 1 1 d . . . . .
C12 C 0.6831(3) 0.7118(3) 0.88416(18) 0.0239(7) Uani 1 1 d . . . . .
C13 C 0.5912(4) 0.7963(3) 0.8781(2) 0.0321(8) Uani 1 1 d . . . . .
H13 H 0.509101 0.771029 0.838665 0.038 Uiso 1 1 calc R U . . .
C14 C 0.6203(5) 0.9176(3) 0.9300(2) 0.0408(9) Uani 1 1 d . . . . .
H14 H 0.557808 0.975692 0.926045 0.049 Uiso 1 1 calc R U . . .
C15 C 0.7399(5) 0.9546(3) 0.9875(2) 0.0433(10) Uani 1 1 d . . . . .
H15 H 0.758940 1.037698 1.022920 0.052 Uiso 1 1 calc R U . . .
C16 C 0.8314(4) 0.8712(4) 0.9935(2) 0.0391(9) Uani 1 1 d . . . . .
H16 H 0.913660 0.897055 1.032789 0.047 Uiso 1 1 calc R U . . .
C17 C 0.8032(4) 0.7503(3) 0.9423(2) 0.0307(8) Uani 1 1 d . . . . .
H17 H 0.866078 0.692693 0.946731 0.037 Uiso 1 1 calc R U . . .
C18 C 0.2342(3) 0.0854(3) 0.80180(17) 0.0205(6) Uani 1 1 d . . . . .
C19 C 0.0909(4) 0.0658(3) 0.81163(18) 0.0245(7) Uani 1 1 d . . . . .
C20 C -0.0053(4) -0.0600(3) 0.8119(2) 0.0313(8) Uani 1 1 d . . . . .
H20 H -0.103561 -0.067334 0.818392 0.038 Uiso 1 1 calc R U . . .
C21 C 0.0437(4) -0.1765(3) 0.8025(2) 0.0357(9) Uani 1 1 d . . . . .
H21 H -0.020875 -0.265237 0.802600 0.043 Uiso 1 1 calc R U . . .
C22 C 0.1867(4) -0.1631(3) 0.7929(2) 0.0377(9) Uani 1 1 d . . . . .
H22 H 0.220606 -0.242974 0.786347 0.045 Uiso 1 1 calc R U . . .
C23 C 0.2820(4) -0.0330(3) 0.7927(2) 0.0301(8) Uani 1 1 d . . . . .
H23 H 0.380351 -0.024949 0.786256 0.036 Uiso 1 1 calc R U . . .
C24 C 0.3153(3) 0.3080(3) 0.73318(17) 0.0203(6) Uani 1 1 d . . . . .
C25 C 0.3314(3) 0.2292(3) 0.80531(17) 0.0186(6) Uani 1 1 d . . . . .
H25 H 0.319751 0.287328 0.853182 0.022 Uiso 1 1 calc R U . . .
C26 C 0.2122(3) 0.3989(3) 0.74027(17) 0.0193(6) Uani 1 1 d . . . . .
C27 C -0.0229(4) 0.4166(4) 0.7077(3) 0.0409(10) Uani 1 1 d . . . . .
H27A H -0.037222 0.428665 0.762612 0.061 Uiso 1 1 calc R U . . .
H27B H -0.115196 0.365112 0.675642 0.061 Uiso 1 1 calc R U . . .
H27C H 0.011677 0.507335 0.691213 0.061 Uiso 1 1 calc R U . . .
C28 C 0.2662(3) 0.2577(3) 0.59191(18) 0.0225(6) Uani 1 1 d . . . . .
C29 C 0.2228(4) 0.1499(3) 0.52160(19) 0.0260(7) Uani 1 1 d . . . . .
C30 C 0.2842(4) 0.0413(3) 0.5110(2) 0.0339(8) Uani 1 1 d . . . . .
H30 H 0.352839 0.030106 0.551252 0.041 Uiso 1 1 calc R U . . .
C31 C 0.2469(5) -0.0500(4) 0.4431(2) 0.0440(10) Uani 1 1 d . . . . .
H31 H 0.291203 -0.122898 0.435522 0.053 Uiso 1 1 calc R U . . .
C32 C 0.1432(5) -0.0351(4) 0.3849(2) 0.0438(10) Uani 1 1 d . . . . .
H32 H 0.117021 -0.097913 0.337566 0.053 Uiso 1 1 calc R U . . .
C33 C 0.0787(4) 0.0707(4) 0.3960(2) 0.0391(9) Uani 1 1 d . . . . .
H33 H 0.006307 0.078583 0.356782 0.047 Uiso 1 1 calc R U . . .
C34 C 0.1180(4) 0.1641(3) 0.4628(2) 0.0337(8) Uani 1 1 d . . . . .
H34 H 0.074992 0.237964 0.469647 0.040 Uiso 1 1 calc R U . . .
H1N H 0.459(4) 0.552(4) 0.814(2) 0.029(10) Uiso 1 1 d . . . . .
H2N H 0.245(4) 0.122(2) 0.665(2) 0.031(10) Uiso 1 1 d 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
C26 O5 C27 114.5(2) . . ?
C9 O2 C10 115.2(3) . . ?
C28 N2 C24 120.4(2) . . ?
C28 N2 H2N 120(2) . . ?
C24 N2 H2N 118(2) . . ?
C11 N1 C7 120.2(3) . . ?
C11 N1 H1N 116(3) . . ?
C7 N1 H1N 124(3) . . ?
C2 C1 C6 115.9(3) . . ?
C2 C1 C8 120.2(3) . . ?
C6 C1 C8 123.7(3) . . ?
F1 C2 C3 119.0(3) . . ?
F1 C2 C1 117.5(3) . . ?
C3 C2 C1 123.5(3) . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 121.7(3) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
N1 C7 C9 112.1(2) . . ?
N1 C7 C8 113.1(2) . . ?
C9 C7 C8 115.6(2) . . ?
N1 C7 C24 112.0(2) . . ?
C9 C7 C24 114.6(2) . . ?
C8 C7 C24 87.4(2) . . ?
C1 C8 C25 119.0(2) . . ?
C1 C8 C7 118.5(2) . . ?
C25 C8 C7 89.0(2) . . ?
C1 C8 H8 109.6 . . ?
C25 C8 H8 109.6 . . ?
C7 C8 H8 109.6 . . ?
O1 C9 O2 125.4(3) . . ?
O1 C9 C7 123.1(3) . . ?
O2 C9 C7 111.5(2) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 N1 122.4(3) . . ?
O3 C11 C12 122.0(3) . . ?
N1 C11 C12 115.6(3) . . ?
C13 C12 C17 119.5(3) . . ?
C13 C12 C11 123.5(3) . . ?
C17 C12 C11 116.9(3) . . ?
C14 C13 C12 119.5(4) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 120.5(3) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C19 C18 C23 116.3(3) . . ?
C19 C18 C25 119.9(3) . . ?
C23 C18 C25 123.8(3) . . ?
F2 C19 C20 118.6(3) . . ?
F2 C19 C18 116.9(3) . . ?
C20 C19 C18 124.5(3) . . ?
C19 C20 C21 118.5(3) . . ?
C19 C20 H20 120.8 . . ?
C21 C20 H20 120.8 . . ?
C22 C21 C20 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 120.7(3) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
N2 C24 C26 113.0(3) . . ?
N2 C24 C25 110.1(2) . . ?
C26 C24 C25 113.8(2) . . ?
N2 C24 C7 111.5(2) . . ?
C26 C24 C7 119.2(2) . . ?
C25 C24 C7 86.3(2) . . ?
C18 C25 C8 121.1(2) . . ?
C18 C25 C24 118.6(2) . . ?
C8 C25 C24 89.7(2) . . ?
C18 C25 H25 108.6 . . ?
C8 C25 H25 108.6 . . ?
C24 C25 H25 108.6 . . ?
O4 C26 O5 124.2(3) . . ?
O4 C26 C24 123.7(3) . . ?
O5 C26 C24 111.9(2) . . ?
O5 C27 H27A 109.5 . . ?
O5 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O5 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O6 C28 N2 120.8(3) . . ?
O6 C28 C29 122.9(3) . . ?
N2 C28 C29 116.3(3) . . ?
C30 C29 C34 119.7(3) . . ?
C30 C29 C28 123.0(3) . . ?
C34 C29 C28 117.3(3) . . ?
C31 C30 C29 120.6(4) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 119.4(4) . . ?
C30 C31 H31 120.3 . . ?
C32 C31 H31 120.3 . . ?
C33 C32 C31 120.2(3) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C34 C33 C32 120.6(4) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C29 119.4(3) . . ?
C33 C34 H34 120.3 . . ?
C29 C34 H34 120.3 . . ?
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 C2 1.345(4) . ?
F2 C19 1.362(4) . ?
O4 C26 1.211(3) . ?
O5 C26 1.315(4) . ?
O5 C27 1.460(4) . ?
O6 C28 1.223(4) . ?
O1 C9 1.209(4) . ?
O2 C9 1.328(4) . ?
O2 C10 1.436(4) . ?
O3 C11 1.230(4) . ?
N2 C28 1.358(4) . ?
N2 C24 1.439(3) . ?
N2 H2N 0.898(18) . ?
N1 C11 1.348(4) . ?
N1 C7 1.445(3) . ?
N1 H1N 0.85(4) . ?
C1 C2 1.379(4) . ?
C1 C6 1.393(4) . ?
C1 C8 1.503(4) . ?
C2 C3 1.373(5) . ?
C3 C4 1.374(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C9 1.523(4) . ?
C7 C8 1.575(4) . ?
C7 C24 1.611(4) . ?
C8 C25 1.539(4) . ?
C8 H8 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.494(4) . ?
C12 C13 1.390(5) . ?
C12 C17 1.395(5) . ?
C13 C14 1.387(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.376(4) . ?
C18 C23 1.394(4) . ?
C18 C25 1.502(4) . ?
C19 C20 1.366(4) . ?
C20 C21 1.384(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.396(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C26 1.529(4) . ?
C24 C25 1.581(4) . ?
C25 H25 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.490(4) . ?
C29 C30 1.386(5) . ?
C29 C34 1.409(5) . ?
C30 C31 1.370(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.397(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.381(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.365(5) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
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
C6 C1 C2 F1 178.4(3) . . . . ?
C8 C1 C2 F1 -5.0(4) . . . . ?
C6 C1 C2 C3 -2.7(5) . . . . ?
C8 C1 C2 C3 173.9(3) . . . . ?
F1 C2 C3 C4 179.9(3) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C3 C4 C5 C6 -0.7(6) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
C2 C1 C6 C5 2.6(5) . . . . ?
C8 C1 C6 C5 -173.8(3) . . . . ?
C11 N1 C7 C9 -54.2(4) . . . . ?
C11 N1 C7 C8 78.5(3) . . . . ?
C11 N1 C7 C24 175.3(3) . . . . ?
C2 C1 C8 C25 157.2(3) . . . . ?
C6 C1 C8 C25 -26.5(4) . . . . ?
C2 C1 C8 C7 -96.7(3) . . . . ?
C6 C1 C8 C7 79.6(4) . . . . ?
N1 C7 C8 C1 -30.7(4) . . . . ?
C9 C7 C8 C1 100.3(3) . . . . ?
C24 C7 C8 C1 -143.5(3) . . . . ?
N1 C7 C8 C25 92.1(3) . . . . ?
C9 C7 C8 C25 -136.8(2) . . . . ?
C24 C7 C8 C25 -20.70(19) . . . . ?
C10 O2 C9 O1 1.0(5) . . . . ?
C10 O2 C9 C7 -175.7(3) . . . . ?
N1 C7 C9 O1 153.6(3) . . . . ?
C8 C7 C9 O1 22.1(4) . . . . ?
C24 C7 C9 O1 -77.4(4) . . . . ?
N1 C7 C9 O2 -29.6(4) . . . . ?
C8 C7 C9 O2 -161.2(3) . . . . ?
C24 C7 C9 O2 99.4(3) . . . . ?
C7 N1 C11 O3 1.3(5) . . . . ?
C7 N1 C11 C12 -178.0(3) . . . . ?
O3 C11 C12 C13 149.4(3) . . . . ?
N1 C11 C12 C13 -31.3(4) . . . . ?
O3 C11 C12 C17 -30.6(4) . . . . ?
N1 C11 C12 C17 148.7(3) . . . . ?
C17 C12 C13 C14 0.0(5) . . . . ?
C11 C12 C13 C14 180.0(3) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C13 C14 C15 C16 0.2(6) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
C15 C16 C17 C12 0.3(5) . . . . ?
C13 C12 C17 C16 -0.2(5) . . . . ?
C11 C12 C17 C16 179.9(3) . . . . ?
C23 C18 C19 F2 177.3(3) . . . . ?
C25 C18 C19 F2 0.3(4) . . . . ?
C23 C18 C19 C20 -0.9(5) . . . . ?
C25 C18 C19 C20 -177.9(3) . . . . ?
F2 C19 C20 C21 -177.5(3) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C20 C21 C22 C23 0.0(6) . . . . ?
C19 C18 C23 C22 0.7(5) . . . . ?
C25 C18 C23 C22 177.5(3) . . . . ?
C21 C22 C23 C18 -0.3(6) . . . . ?
C28 N2 C24 C26 54.3(4) . . . . ?
C28 N2 C24 C25 -177.3(3) . . . . ?
C28 N2 C24 C7 -83.2(3) . . . . ?
N1 C7 C24 N2 156.1(2) . . . . ?
C9 C7 C24 N2 27.1(3) . . . . ?
C8 C7 C24 N2 -89.9(3) . . . . ?
N1 C7 C24 C26 21.6(4) . . . . ?
C9 C7 C24 C26 -107.5(3) . . . . ?
C8 C7 C24 C26 135.5(3) . . . . ?
N1 C7 C24 C25 -93.7(3) . . . . ?
C9 C7 C24 C25 137.2(2) . . . . ?
C8 C7 C24 C25 20.17(19) . . . . ?
C19 C18 C25 C8 175.8(3) . . . . ?
C23 C18 C25 C8 -1.0(4) . . . . ?
C19 C18 C25 C24 -75.4(4) . . . . ?
C23 C18 C25 C24 107.8(3) . . . . ?
C1 C8 C25 C18 -92.8(3) . . . . ?
C7 C8 C25 C18 144.8(3) . . . . ?
C1 C8 C25 C24 143.5(2) . . . . ?
C7 C8 C25 C24 21.08(19) . . . . ?
N2 C24 C25 C18 -34.9(4) . . . . ?
C26 C24 C25 C18 93.1(3) . . . . ?
C7 C24 C25 C18 -146.5(2) . . . . ?
N2 C24 C25 C8 91.0(3) . . . . ?
C26 C24 C25 C8 -141.0(2) . . . . ?
C7 C24 C25 C8 -20.64(19) . . . . ?
C27 O5 C26 O4 0.1(5) . . . . ?
C27 O5 C26 C24 175.1(3) . . . . ?
N2 C24 C26 O4 -160.4(3) . . . . ?
C25 C24 C26 O4 73.1(4) . . . . ?
C7 C24 C26 O4 -26.4(4) . . . . ?
N2 C24 C26 O5 24.6(4) . . . . ?
C25 C24 C26 O5 -101.8(3) . . . . ?
C7 C24 C26 O5 158.6(3) . . . . ?
C24 N2 C28 O6 3.0(5) . . . . ?
C24 N2 C28 C29 -177.5(3) . . . . ?
O6 C28 C29 C30 134.2(4) . . . . ?
N2 C28 C29 C30 -45.3(4) . . . . ?
O6 C28 C29 C34 -43.5(5) . . . . ?
N2 C28 C29 C34 137.0(3) . . . . ?
C34 C29 C30 C31 1.8(5) . . . . ?
C28 C29 C30 C31 -175.8(3) . . . . ?
C29 C30 C31 C32 -1.6(6) . . . . ?
C30 C31 C32 C33 -0.2(6) . . . . ?
C31 C32 C33 C34 1.8(6) . . . . ?
C32 C33 C34 C29 -1.5(6) . . . . ?
C30 C29 C34 C33 -0.2(5) . . . . ?
C28 C29 C34 C33 177.5(3) . . . . ?
