#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024480.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_4024480
loop_
_publ_author_name
'Santos Fustero'
'Gema Chiva'
'Julio Piera'
'Juan F. Sanz-Cervera'
'Alessandro Volonterio'
'Matteo Zanda'
'Carmen Ramírez de Arellano'
_publ_contact_author_address
;Departamento de Química Orgánica
Universidad de Valencia
46100 Valencia
Spain
;
_publ_contact_author_email       Carmen.ramirezdearellano@uv.es
_publ_contact_author_fax         +34963544939
_publ_contact_author_name        'Carmen Ramírez de Arellano'
_publ_contact_author_phone       +34963543046
_publ_section_title
;
New Fluorinated Peptidomimetics through Tandem Aza-Michael Addition to
α-Trifluoromethyl Acrylamide Acceptors: Synthesis and Conformational Study
in Solid State and Solution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3122
_journal_page_last               3132
_journal_paper_doi               10.1021/jo9001867
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_sum            'C17 H24 F6 N2 O4'
_chemical_formula_weight         434.38
_chemical_name_common            gt319a
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.52(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.504(2)
_cell_length_b                   9.4224(19)
_cell_length_c                   11.523(2)
_cell_measurement_reflns_used    2424
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1068.1(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'SHELXTL v6.14 (Bruker, 2000-2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       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  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4203
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         5.12
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       spike
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(3)
_refine_ls_extinction_coef       0.09(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         2297
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.0813
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1538P)²+0.2576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2143
_refine_ls_wR_factor_ref         0.2623
_reflns_number_gt                1290
_reflns_number_total             2297
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9001867_si_002_4.cif
_cod_data_source_block           gt319_compound_13
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4024480
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 1.1036(6) 0.6499(5) 0.8422(6) 0.0917(16) Uani 1 1 d . . .
O3 O 0.9334(7) 0.6603(5) 1.0534(6) 0.1020(19) Uani 1 1 d . . .
N7 N 1.1044(7) 0.8661(6) 0.9277(7) 0.0830(17) Uani 1 1 d D . .
H7 H 1.062(11) 0.945(7) 0.901(11) 0.15(5) Uiso 1 1 d D . .
N3 N 0.8353(7) 0.8744(6) 1.0520(5) 0.0791(17) Uani 1 1 d D . .
H3 H 0.853(10) 0.964(3) 1.064(10) 0.11(3) Uiso 1 1 d D . .
C2 C 0.6961(9) 0.8238(10) 0.9991(7) 0.103(3) Uani 1 1 d . . .
H2 H 0.6985 0.7179 0.9957 0.123 Uiso 1 1 calc R . .
C1 C 0.6365(9) 0.8791(11) 0.8667(9) 0.107(3) Uani 1 1 d . . .
O1 O 0.6588(12) 0.9923(12) 0.8343(8) 0.220(7) Uani 1 1 d . . .
C10 C 1.0232(18) 0.9728(11) 0.6748(12) 0.143(5) Uani 1 1 d . . .
H10B H 0.9870 1.0027 0.5908 0.172 Uiso 1 1 calc R . .
H10A H 1.0676 1.0392 0.7381 0.172 Uiso 1 1 calc R . .
C9 C 1.0117(10) 0.8379(9) 0.7037(8) 0.094(3) Uani 1 1 d . . .
C8 C 1.0789(8) 0.7785(7) 0.8324(8) 0.078(2) Uani 1 1 d . . .
C6 C 1.1687(9) 0.8237(8) 1.0542(8) 0.090(2) Uani 1 1 d . . .
H6A H 1.2577 0.8721 1.0899 0.107 Uiso 1 1 calc R . .
H6B H 1.1853 0.7201 1.0582 0.107 Uiso 1 1 calc R . .
C5 C 1.0804(7) 0.8608(7) 1.1291(6) 0.076(2) Uani 1 1 d . . .
H5 H 1.0670 0.9660 1.1259 0.091 Uiso 1 1 calc R . .
C4 C 0.9411(9) 0.7903(6) 1.0764(5) 0.074(2) Uani 1 1 d . . .
O2 O 0.5510(5) 0.7888(5) 0.7965(4) 0.0793(14) Uani 1 1 d . A .
C11 C 0.4704(7) 0.8188(9) 0.6618(6) 0.0758(19) Uani 1 1 d . . .
C12 C 0.3880(17) 0.952(2) 0.6466(14) 0.102(6) Uani 0.74(3) 1 d P A 1
H12D H 0.3343 0.9478 0.7010 0.122 Uiso 0.74(3) 1 calc PR A 1
H12E H 0.3269 0.9600 0.5602 0.122 Uiso 0.74(3) 1 calc PR A 1
H12F H 0.4489 1.0339 0.6685 0.122 Uiso 0.74(3) 1 calc PR A 1
C13 C 0.372(2) 0.6924(17) 0.6237(11) 0.114(7) Uani 0.74(3) 1 d P A 1
H13D H 0.3059 0.6988 0.6659 0.137 Uiso 0.74(3) 1 calc PR A 1
H13E H 0.4234 0.6036 0.6471 0.137 Uiso 0.74(3) 1 calc PR A 1
H13F H 0.3243 0.6941 0.5338 0.137 Uiso 0.74(3) 1 calc PR A 1
C14 C 0.5566(12) 0.818(3) 0.5868(11) 0.125(6) Uani 0.74(3) 1 d P A 1
H14D H 0.5973 0.7234 0.5906 0.150 Uiso 0.74(3) 1 calc PR A 1
H14E H 0.6288 0.8886 0.6187 0.150 Uiso 0.74(3) 1 calc PR A 1
H14F H 0.5019 0.8402 0.5007 0.150 Uiso 0.74(3) 1 calc PR A 1
C12' C 0.5628(12) 0.897(3) 0.6039(11) 0.102(16) Uiso 0.26(3) 1 d PR A 2
H12A H 0.5844 0.9917 0.6406 0.123 Uiso 0.26(3) 1 calc PR A 2
H12B H 0.5156 0.9057 0.5142 0.123 Uiso 0.26(3) 1 calc PR A 2
H12C H 0.6471 0.8431 0.6200 0.123 Uiso 0.26(3) 1 calc PR A 2
C13' C 0.352(4) 0.890(5) 0.677(4) 0.086(11) Uiso 0.26(3) 1 d P A 2
H13A H 0.2810 0.9030 0.5953 0.104 Uiso 0.26(3) 1 calc PR A 2
H13B H 0.3794 0.9827 0.7161 0.104 Uiso 0.26(3) 1 calc PR A 2
H13C H 0.3164 0.8315 0.7289 0.104 Uiso 0.26(3) 1 calc PR A 2
C14' C 0.467(6) 0.677(5) 0.613(4) 0.105(13) Uiso 0.26(3) 1 d P A 2
H14A H 0.5597 0.6432 0.6294 0.125 Uiso 0.26(3) 1 calc PR A 2
H14B H 0.4165 0.6772 0.5238 0.125 Uiso 0.26(3) 1 calc PR A 2
H14C H 0.4212 0.6130 0.6538 0.125 Uiso 0.26(3) 1 calc PR A 2
C16 C 0.674(2) 0.814(3) 1.2090(15) 0.209(9) Uani 1 1 d . . .
H16A H 0.5998 0.7854 1.2363 0.251 Uiso 1 1 calc R . .
H16B H 0.7251 0.8921 1.2614 0.251 Uiso 1 1 calc R . .
H16C H 0.7353 0.7337 1.2155 0.251 Uiso 1 1 calc R . .
C15 C 0.6172(18) 0.864(4) 1.0761(19) 0.236(13) Uani 1 1 d . . .
H15 H 0.5348 0.8022 1.0416 0.283 Uiso 1 1 calc R . .
C17 C 0.563(2) 0.995(2) 1.0547(18) 0.184(7) Uani 1 1 d . . .
H17A H 0.5615 1.0291 0.9739 0.221 Uiso 1 1 calc R . .
H17B H 0.6173 1.0600 1.1197 0.221 Uiso 1 1 calc R . .
H17C H 0.4694 0.9924 1.0550 0.221 Uiso 1 1 calc R . .
C18 C 1.1467(12) 0.8185(9) 1.2609(9) 0.106(3) Uani 1 1 d . . .
C19 C 0.9427(14) 0.7347(14) 0.6054(10) 0.116(3) Uani 1 1 d . . .
F4 F 1.0266(9) 0.6452(9) 0.5829(7) 0.158(3) Uani 1 1 d . . .
F5 F 0.8662(11) 0.7988(11) 0.5005(6) 0.179(4) Uani 1 1 d . . .
F6 F 0.8550(6) 0.6567(8) 0.6402(6) 0.132(2) Uani 1 1 d . . .
F1 F 1.2632(6) 0.8917(7) 1.3164(5) 0.131(2) Uani 1 1 d . . .
F2 F 1.1824(8) 0.6796(6) 1.2760(5) 0.134(2) Uani 1 1 d . . .
F3 F 1.0716(7) 0.8398(6) 1.3305(4) 0.1157(19) Uani 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'
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
C8 N7 C6 123.8(6) . . ?
C8 N7 H7 108(9) . . ?
C6 N7 H7 127(9) . . ?
C4 N3 C2 122.9(7) . . ?
C4 N3 H3 116(7) . . ?
C2 N3 H3 121(7) . . ?
N3 C2 C15 111.3(13) . . ?
N3 C2 C1 107.9(7) . . ?
C15 C2 C1 113.5(10) . . ?
N3 C2 H2 108.0 . . ?
C15 C2 H2 108.0 . . ?
C1 C2 H2 108.0 . . ?
O1 C1 O2 124.6(8) . . ?
O1 C1 C2 124.6(8) . . ?
O2 C1 C2 110.6(8) . . ?
C9 C10 H10B 120.0 . . ?
C9 C10 H10A 120.0 . . ?
H10B C10 H10A 120.0 . . ?
C10 C9 C19 120.0(10) . . ?
C10 C9 C8 123.3(11) . . ?
C19 C9 C8 116.4(7) . . ?
O4 C8 N7 124.1(8) . . ?
O4 C8 C9 117.7(8) . . ?
N7 C8 C9 118.2(6) . . ?
N7 C6 C5 110.6(6) . . ?
N7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C18 C5 C6 111.0(7) . . ?
C18 C5 C4 109.3(7) . . ?
C6 C5 C4 111.5(6) . . ?
C18 C5 H5 108.3 . . ?
C6 C5 H5 108.3 . . ?
C4 C5 H5 108.3 . . ?
O3 C4 N3 124.0(8) . . ?
O3 C4 C5 119.5(8) . . ?
N3 C4 C5 116.3(5) . . ?
C1 O2 C11 122.3(6) . . ?
C14' C11 C14 73(2) . . ?
C14' C11 C13' 124(3) . . ?
C14 C11 C13' 143(2) . . ?
C14' C11 C12 142(2) . . ?
C14 C11 C12 113.1(12) . . ?
C13' C11 C12 32.6(15) . . ?
C14' C11 O2 98.8(18) . . ?
C14 C11 O2 111.5(6) . . ?
C13' C11 O2 99.0(17) . . ?
C12 C11 O2 111.7(8) . . ?
C14' C11 C13 41.2(19) . . ?
C14 C11 C13 108.7(12) . . ?
C13' C11 C13 82.8(18) . . ?
C12 C11 C13 108.1(10) . . ?
O2 C11 C13 103.1(7) . . ?
C14' C11 C12' 102(2) . . ?
C14 C11 C12' 29.6(3) . . ?
C13' C11 C12' 121(2) . . ?
C12 C11 C12' 88.6(12) . . ?
O2 C11 C12' 108.8(6) . . ?
C13 C11 C12' 135.0(11) . . ?
C11 C12 H12D 109.5 . . ?
C11 C12 H12E 109.5 . . ?
H12D C12 H12E 109.5 . . ?
C11 C12 H12F 109.5 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 109.5 . . ?
C11 C13 H13D 109.5 . . ?
C11 C13 H13E 109.5 . . ?
H13D C13 H13E 109.5 . . ?
C11 C13 H13F 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
C11 C14 H14D 109.5 . . ?
C11 C14 H14E 109.5 . . ?
H14D C14 H14E 109.5 . . ?
C11 C14 H14F 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
C11 C12' H12A 109.5 . . ?
C11 C12' H12B 109.5 . . ?
H12A C12' H12B 109.5 . . ?
C11 C12' H12C 109.5 . . ?
H12A C12' H12C 109.5 . . ?
H12B C12' H12C 109.5 . . ?
C11 C13' H13A 109.5 . . ?
C11 C13' H13B 109.5 . . ?
H13A C13' H13B 109.5 . . ?
C11 C13' H13C 109.5 . . ?
H13A C13' H13C 109.5 . . ?
H13B C13' H13C 109.5 . . ?
C11 C14' H14A 109.5 . . ?
C11 C14' H14B 109.5 . . ?
H14A C14' H14B 109.5 . . ?
C11 C14' H14C 109.5 . . ?
H14A C14' H14C 109.5 . . ?
H14B C14' H14C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C15 C2 114.8(13) . . ?
C17 C15 C16 117(3) . . ?
C2 C15 C16 115.4(14) . . ?
C17 C15 H15 101.9 . . ?
C2 C15 H15 101.9 . . ?
C16 C15 H15 101.9 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F3 C18 F1 105.6(8) . . ?
F3 C18 F2 105.4(10) . . ?
F1 C18 F2 105.5(8) . . ?
F3 C18 C5 114.4(8) . . ?
F1 C18 C5 111.6(9) . . ?
F2 C18 C5 113.6(8) . . ?
F4 C19 F5 110.2(9) . . ?
F4 C19 F6 106.6(11) . . ?
F5 C19 F6 105.0(10) . . ?
F4 C19 C9 113.1(10) . . ?
F5 C19 C9 111.9(10) . . ?
F6 C19 C9 109.5(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
O4 C8 1.236(8) . ?
O3 C4 1.250(8) . ?
N7 C8 1.324(10) . ?
N7 C6 1.432(11) . ?
N7 H7 0.86(2) . ?
N3 C4 1.313(10) . ?
N3 C2 1.453(11) . ?
N3 H3 0.86(2) . ?
C2 C15 1.46(2) . ?
C2 C1 1.524(12) . ?
C2 H2 1.0000 . ?
C1 O1 1.180(12) . ?
C1 O2 1.294(10) . ?
C10 C9 1.330(14) . ?
C10 H10B 0.9500 . ?
C10 H10A 0.9500 . ?
C9 C19 1.476(16) . ?
C9 C8 1.509(11) . ?
C6 C5 1.514(12) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C5 C18 1.486(11) . ?
C5 C4 1.526(11) . ?
C5 H5 1.0000 . ?
O2 C11 1.512(8) . ?
C11 C14' 1.45(5) . ?
C11 C14 1.455(14) . ?
C11 C13' 1.48(4) . ?
C11 C12 1.496(15) . ?
C11 C13 1.537(16) . ?
C11 C12' 1.544(18) . ?
C12 H12D 0.9800 . ?
C12 H12E 0.9800 . ?
C12 H12F 0.9800 . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?
C14 H14D 0.9800 . ?
C14 H14E 0.9800 . ?
C14 H14F 0.9800 . ?
C12' H12A 0.9800 . ?
C12' H12B 0.9800 . ?
C12' H12C 0.9800 . ?
C13' H13A 0.9800 . ?
C13' H13B 0.9800 . ?
C13' H13C 0.9800 . ?
C14' H14A 0.9800 . ?
C14' H14B 0.9800 . ?
C14' H14C 0.9800 . ?
C16 C15 1.51(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 C17 1.35(3) . ?
C15 H15 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 F3 1.323(14) . ?
C18 F1 1.354(11) . ?
C18 F2 1.356(11) . ?
C19 F4 1.310(13) . ?
C19 F5 1.338(13) . ?
C19 F6 1.345(13) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O4 0.86(2) 2.02(4) 2.843(8) 158(10) 2_757
N7 H7 O3 0.86(2) 2.10(8) 2.820(7) 141(11) 2_757
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
C4 N3 C2 C15 124.8(12) . . . . ?
C4 N3 C2 C1 -110.0(9) . . . . ?
N3 C2 C1 O1 -37.6(19) . . . . ?
C15 C2 C1 O1 86(2) . . . . ?
N3 C2 C1 O2 146.8(8) . . . . ?
C15 C2 C1 O2 -89.4(17) . . . . ?
C6 N7 C8 O4 2.5(13) . . . . ?
C6 N7 C8 C9 -179.4(8) . . . . ?
C10 C9 C8 O4 -154.8(10) . . . . ?
C19 C9 C8 O4 18.7(12) . . . . ?
C10 C9 C8 N7 27.0(13) . . . . ?
C19 C9 C8 N7 -159.5(8) . . . . ?
C8 N7 C6 C5 -124.0(8) . . . . ?
N7 C6 C5 C18 -179.5(6) . . . . ?
N7 C6 C5 C4 58.3(7) . . . . ?
C2 N3 C4 O3 2.3(11) . . . . ?
C2 N3 C4 C5 178.7(7) . . . . ?
C18 C5 C4 O3 -73.2(9) . . . . ?
C6 C5 C4 O3 50.0(8) . . . . ?
C18 C5 C4 N3 110.2(7) . . . . ?
C6 C5 C4 N3 -126.6(7) . . . . ?
O1 C1 O2 C11 0.9(19) . . . . ?
C2 C1 O2 C11 176.6(7) . . . . ?
C1 O2 C11 C14' 145(2) . . . . ?
C1 O2 C11 C14 70.7(16) . . . . ?
C1 O2 C11 C13' -88(2) . . . . ?
C1 O2 C11 C12 -56.9(14) . . . . ?
C1 O2 C11 C13 -172.9(12) . . . . ?
C1 O2 C11 C12' 39.3(14) . . . . ?
N3 C2 C15 C17 85(2) . . . . ?
C1 C2 C15 C17 -37(3) . . . . ?
N3 C2 C15 C16 -56(3) . . . . ?
C1 C2 C15 C16 -178.5(18) . . . . ?
C6 C5 C18 F3 -176.0(7) . . . . ?
C4 C5 C18 F3 -52.6(9) . . . . ?
C6 C5 C18 F1 64.1(10) . . . . ?
C4 C5 C18 F1 -172.5(8) . . . . ?
C6 C5 C18 F2 -55.0(12) . . . . ?
C4 C5 C18 F2 68.4(12) . . . . ?
C10 C9 C19 F4 107.7(13) . . . . ?
C8 C9 C19 F4 -66.0(12) . . . . ?
C10 C9 C19 F5 -17.5(15) . . . . ?
C8 C9 C19 F5 168.8(8) . . . . ?
C10 C9 C19 F6 -133.5(11) . . . . ?
C8 C9 C19 F6 52.8(12) . . . . ?
C4 C5 C6 N7 58.3(7) . . . . ?
N3 C4 C5 C6 -126.6(7) . . . . ?
C1 C2 N3 C4 -110.0(9) . . . . ?
O2 C1 C2 N3 146.8(8) . . . . ?
