#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/38/2223853.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223853
loop_
_publ_author_name
'Eberle, Marcel K.'
'Stoeckli-Evans, Helen'
'Keese, Reinhart'
_publ_section_title
;
 (RSS)-[N-Hydroxyethyloxy]-hexafluoroVal--MeLeu--Ala
 tert-butyl ester
;
_journal_coeditor_code           IM2143
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2900
_journal_paper_doi               10.1107/S1600536809042974
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H35 F6 N3 O6'
_chemical_formula_moiety         'C21 H35 F6 N3 O6'
_chemical_formula_sum            'C21 H35 F6 N3 O6'
_chemical_formula_weight         539.52
_chemical_name_common
;
(RSS)-[N-Hydroxyethyloxy]-hexafluoroVal--MeLeu--Ala
tert-butyl ester
;
_chemical_name_systematic
;
(2S,5S,8R)-tert-butyl
8-(1,1,1,3,3,3-hexafluoropropan-2-yl)-12-hydroxy-5-isobutyl-2,6-dimethyl-
4,7-dioxo-10-oxa-3,6,9-triazadodecanoate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1608(7)
_cell_length_b                   11.2088(7)
_cell_length_c                   21.2562(15)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      2.06
_cell_volume                     2659.1(3)
_computing_cell_refinement       'CELL in IPDS-I (Stoe & Cie, 2000)'
_computing_data_collection       'EXPOSE in IPDS-I (Stoe & Cie, 2000)'
_computing_data_reduction        'INTEGRATE in IPDS-I (Stoe & Cie, 2000)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'phi oscillation'
_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  0.0632
_diffrn_reflns_av_sigmaI/netI    0.0327
_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       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18889
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.88
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.374
_refine_ls_abs_structure_details 'none; the 2234 Friedel pairs were merged'
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0769
_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)+(0.0533P)²+7.6569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.2012
_reflns_number_gt                2554
_reflns_number_total             2917
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2143.cif
_cod_data_source_block           I
_cod_database_code               2223853
_cod_database_fobs_code          2223853
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
F F1 0.8576(6) 0.5625(5) 0.7742(2) 0.0700(19) Uani . . 1.000
F F2 1.0348(6) 0.6382(5) 0.7580(2) 0.083(2) Uani . . 1.000
F F3 0.9114(5) 0.7225(4) 0.82195(18) 0.0505(14) Uani . . 1.000
F F4 0.9183(4) 0.3504(4) 0.8362(2) 0.0513(16) Uani . . 1.000
F F5 1.0984(5) 0.3567(4) 0.8715(3) 0.0623(18) Uani . . 1.000
F F6 1.0617(5) 0.4058(4) 0.7766(2) 0.0670(19) Uani . . 1.000
O O1 0.9061(4) 0.6526(4) 1.24644(19) 0.0343(12) Uani . . 1.000
O O2 0.9956(5) 0.6041(6) 1.1539(3) 0.0573(19) Uani . . 1.000
O O3 0.7713(5) 0.9284(4) 1.0905(2) 0.0357(14) Uani . . 1.000
O O4 1.0307(4) 0.7163(4) 0.9528(2) 0.0403(17) Uani . . 1.000
O O5A 0.9190(14) 0.4938(14) 1.0180(7) 0.042(4) Uani . . 0.543(9)
O O6A 0.6768(14) 0.4094(14) 1.0107(12) 0.127(8) Uani . . 0.543(9)
N N1 0.8327(6) 0.7356(5) 1.0887(3) 0.0387(19) Uani . . 1.000
N N2 0.8262(5) 0.7377(5) 0.9574(2) 0.0270(16) Uani . . 1.000
N N3A 0.982(2) 0.473(3) 0.9578(16) 0.031(6) Uani . . 0.543(9)
C C1 0.9169(7) 0.6529(6) 1.1836(3) 0.0350(19) Uani . . 1.000
C C2 0.8107(6) 0.7148(6) 1.1547(3) 0.0337(19) Uani . . 1.000
C C3 0.6980(7) 0.6393(8) 1.1630(3) 0.045(3) Uani . . 1.000
C C4 0.9872(7) 0.5833(7) 1.2875(3) 0.039(2) Uani . . 1.000
C C5 1.1153(8) 0.6268(9) 1.2817(4) 0.061(3) Uani . . 1.000
C C6 0.9761(9) 0.4527(7) 1.2725(4) 0.060(3) Uani . . 1.000
C C7 0.9347(8) 0.6062(8) 1.3525(3) 0.050(3) Uani . . 1.000
C C8 0.8089(5) 0.8426(6) 1.0615(3) 0.0260(17) Uani . . 1.000
C C9 0.8399(6) 0.8523(5) 0.9904(3) 0.0293(17) Uani . . 1.000
C C14 0.9274(7) 0.6796(6) 0.9424(3) 0.0337(19) Uani . . 1.000
C C15 0.9200(7) 0.5526(6) 0.9140(3) 0.0330(19) Uani . . 1.000
C C16 1.0017(7) 0.5429(6) 0.8559(3) 0.036(2) Uani . . 1.000
C C17 1.0167(7) 0.4139(7) 0.8347(4) 0.041(2) Uani . . 1.000
C C18 0.9518(8) 0.6150(7) 0.8028(3) 0.044(2) Uani . . 1.000
C C19 0.7068(6) 0.6926(7) 0.9431(4) 0.044(2) Uani . . 1.000
C C20 0.7694(7) 0.9544(6) 0.9583(3) 0.0357(19) Uani . . 1.000
C C21 0.7368(9) 1.0861(8) 0.8671(4) 0.056(3) Uani . . 1.000
C C22 0.8160(9) 0.9903(7) 0.8948(4) 0.059(3) Uani . . 1.000
C C23A 0.9457(15) 1.0506(16) 0.9098(8) 0.056(3) Uani . . 0.500
C C23B 0.9385(14) 1.0120(17) 0.8825(8) 0.056(3) Uani . . 0.500
C C24A 0.8850(19) 0.3851(14) 1.0521(10) 0.080(4) Uani . . 0.543(9)
C C25A 0.7784(17) 0.3265(15) 1.0138(12) 0.080(4) Uani . . 0.543(9)
N N3B 0.947(3) 0.465(4) 0.966(2) 0.031(6) Uani . . 0.457(9)
O O5B 0.8575(18) 0.4829(19) 1.0142(11) 0.059(6) Uani . . 0.457(9)
O O6B 0.9684(16) 0.2308(12) 1.0006(7) 0.073(6) Uani . . 0.457(9)
C C24B 0.803(2) 0.3747(19) 1.0197(15) 0.080(4) Uani . . 0.457(9)
C C25B 0.882(2) 0.2763(17) 1.0439(11) 0.080(4) Uani . . 0.457(9)
H H3A1 1.04260 0.42520 0.95020 0.0380 Uiso calc . 0.543(9)
H H3C 0.67350 0.64060 1.20730 0.0680 Uiso calc R 1.000
H H5A 1.11730 0.71370 1.28630 0.0920 Uiso calc R 1.000
H H1N 0.860(7) 0.667(4) 1.075(3) 0.0470 Uiso . . 1.000
H H2 0.79870 0.79330 1.17620 0.0400 Uiso calc R 1.000
H H6A1 0.61320 0.37270 1.01920 0.1510 Uiso calc . 0.543(9)
H H3A 0.63350 0.67190 1.13690 0.0680 Uiso calc R 1.000
H H3B 0.71470 0.55700 1.15020 0.0680 Uiso calc R 1.000
H H7A 0.85130 0.57900 1.35360 0.0760 Uiso calc R 1.000
H H7B 0.93780 0.69180 1.36170 0.0760 Uiso calc R 1.000
H H7C 0.98130 0.56260 1.38410 0.0760 Uiso calc R 1.000
H H9 0.92660 0.87400 0.98770 0.0350 Uiso calc R 1.000
H H15 0.83580 0.52690 0.90530 0.0400 Uiso calc R 1.000
H H16 1.08230 0.57540 0.86710 0.0430 Uiso calc R 1.000
H H19A 0.69300 0.69650 0.89760 0.0660 Uiso calc R 1.000
H H19B 0.64680 0.74140 0.96480 0.0660 Uiso calc R 1.000
H H19C 0.70030 0.60970 0.95730 0.0660 Uiso calc R 1.000
H H20A 0.68480 0.92950 0.95380 0.0430 Uiso calc R 1.000
H H20B 0.77110 1.02510 0.98630 0.0430 Uiso calc R 1.000
H H21A 0.65580 1.05440 0.86110 0.0840 Uiso calc R 1.000
H H21B 0.73380 1.15450 0.89580 0.0840 Uiso calc R 1.000
H H21C 0.76950 1.11160 0.82650 0.0840 Uiso calc R 1.000
H H22A 0.82370 0.92020 0.86600 0.0710 Uiso calc . 0.500
H H22B 0.80410 0.91870 0.86740 0.0710 Uiso . . 0.500
H H23A 1.00580 0.98780 0.91550 0.0840 Uiso calc . 0.500
H H23B 0.94010 1.09830 0.94840 0.0840 Uiso calc . 0.500
H H23C 0.96930 1.10210 0.87470 0.0840 Uiso calc . 0.500
H H23D 0.96630 1.07870 0.90850 0.0840 Uiso calc . 0.500
H H23E 0.94910 1.03180 0.83800 0.0840 Uiso calc . 0.500
H H23F 0.98520 0.94050 0.89260 0.0840 Uiso calc . 0.500
H H24A 0.85890 0.40490 1.09540 0.0950 Uiso calc . 0.543(9)
H H24B 0.95370 0.32950 1.05460 0.0950 Uiso calc . 0.543(9)
H H25A 0.80560 0.30680 0.97070 0.0950 Uiso calc . 0.543(9)
H H25B 0.75300 0.25160 1.03460 0.0950 Uiso calc . 0.543(9)
H H5B 1.14720 0.60460 1.24040 0.0920 Uiso calc R 1.000
H H5C 1.16430 0.59010 1.31480 0.0920 Uiso calc R 1.000
H H6A 1.00380 0.43820 1.22940 0.0900 Uiso calc R 1.000
H H6B 0.89210 0.42830 1.27640 0.0900 Uiso calc R 1.000
H H6C 1.02510 0.40650 1.30200 0.0900 Uiso calc R 1.000
H H3B1 1.00600 0.41330 0.96670 0.0380 Uiso calc . 0.457(9)
H H6B1 0.97770 0.27970 0.97100 0.0880 Uiso calc . 0.457(9)
H H24C 0.77180 0.35110 0.97790 0.0950 Uiso calc . 0.457(9)
H H24D 0.73370 0.38290 1.04840 0.0950 Uiso calc . 0.457(9)
H H25C 0.92560 0.30610 1.08140 0.0950 Uiso calc . 0.457(9)
H H25D 0.83080 0.20940 1.05780 0.0950 Uiso calc . 0.457(9)
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 0.0000 '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 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C4 . . . 122.3(5) no
N3A O5A C24A . . . 114.8(18) no
N3B O5B C24B . . . 104(3) no
C25A O6A H6A1 . . . 109.00 no
C25B O6B H6B1 . . . 109.00 no
C2 N1 C8 . . . 121.6(6) no
C9 N2 C19 . . . 119.8(5) no
C9 N2 C14 . . . 116.7(6) no
C14 N2 C19 . . . 123.5(6) no
O5A N3A C15 . . . 103.3(18) no
O5B N3B C15 . . . 107(3) no
C8 N1 H1N . . . 135(4) no
C2 N1 H1N . . . 104(4) no
C15 N3A H3A1 . . . 128.00 no
O5A N3A H3A1 . . . 128.00 no
C15 N3B H3B1 . . . 126.00 no
O5B N3B H3B1 . . . 127.00 no
O1 C1 O2 . . . 125.6(7) no
O1 C1 C2 . . . 109.7(6) no
O2 C1 C2 . . . 124.5(6) no
C1 C2 C3 . . . 110.3(6) no
N1 C2 C3 . . . 110.0(5) no
N1 C2 C1 . . . 109.7(6) no
C5 C4 C6 . . . 112.0(7) no
O1 C4 C7 . . . 102.2(6) no
O1 C4 C6 . . . 109.6(6) no
C6 C4 C7 . . . 109.0(7) no
O1 C4 C5 . . . 111.1(6) no
C5 C4 C7 . . . 112.5(6) no
O3 C8 N1 . . . 123.4(6) no
N1 C8 C9 . . . 115.6(6) no
O3 C8 C9 . . . 120.9(6) no
C8 C9 C20 . . . 111.6(5) no
N2 C9 C8 . . . 112.3(5) no
N2 C9 C20 . . . 112.5(5) no
N2 C14 C15 . . . 119.6(6) no
O4 C14 C15 . . . 115.0(6) no
O4 C14 N2 . . . 125.3(6) no
N3B C15 C14 . . . 107.6(17) no
C14 C15 C16 . . . 110.3(6) no
N3A C15 C14 . . . 106.7(14) no
N3A C15 C16 . . . 100.8(12) no
N3B C15 C16 . . . 115.1(15) no
C15 C16 C18 . . . 110.3(6) no
C17 C16 C18 . . . 109.3(6) no
C15 C16 C17 . . . 111.7(6) no
F6 C17 C16 . . . 112.3(6) no
F5 C17 F6 . . . 104.3(6) no
F4 C17 C16 . . . 114.6(6) no
F4 C17 F5 . . . 107.0(6) no
F4 C17 F6 . . . 107.5(6) no
F5 C17 C16 . . . 110.5(6) no
F1 C18 F3 . . . 105.4(7) no
F2 C18 F3 . . . 105.6(6) no
F3 C18 C16 . . . 112.3(5) no
F2 C18 C16 . . . 112.3(7) no
F1 C18 F2 . . . 107.5(5) no
F1 C18 C16 . . . 113.2(6) no
C9 C20 C22 . . . 114.7(6) no
C20 C22 C23A . . . 104.1(8) no
C23A C22 C23B . . . 26.5(10) no
C20 C22 C21 . . . 109.8(7) no
C21 C22 C23B . . . 111.8(10) no
C21 C22 C23A . . . 107.5(9) no
C20 C22 C23B . . . 123.2(10) no
C22 C23A C23B . . . 60.0(17) no
C22 C23B C23A . . . 94(2) no
O5A C24A C25A . . . 106.5(16) no
O5B C24B C25B . . . 114.9(19) no
O6A C25A C24A . . . 109.9(15) no
O6B C25B C24B . . . 116(2) no
N1 C2 H2 . . . 109.00 no
C1 C2 H2 . . . 109.00 no
C3 C2 H2 . . . 109.00 no
C2 C3 H3A . . . 109.00 no
H3A C3 H3C . . . 109.00 no
H3B C3 H3C . . . 109.00 no
C2 C3 H3B . . . 109.00 no
C2 C3 H3C . . . 109.00 no
H3A C3 H3B . . . 109.00 no
C4 C5 H5A . . . 109.00 no
C4 C5 H5B . . . 110.00 no
C4 C5 H5C . . . 109.00 no
H5B C5 H5C . . . 109.00 no
H5A C5 H5B . . . 110.00 no
H5A C5 H5C . . . 109.00 no
C4 C6 H6A . . . 109.00 no
C4 C6 H6B . . . 109.00 no
C4 C6 H6C . . . 109.00 no
H6A C6 H6B . . . 110.00 no
H6B C6 H6C . . . 109.00 no
H6A C6 H6C . . . 110.00 no
C4 C7 H7C . . . 109.00 no
H7A C7 H7B . . . 109.00 no
H7B C7 H7C . . . 109.00 no
C4 C7 H7A . . . 110.00 no
H7A C7 H7C . . . 109.00 no
C4 C7 H7B . . . 109.00 no
N2 C9 H9 . . . 107.00 no
C8 C9 H9 . . . 107.00 no
C20 C9 H9 . . . 107.00 no
C14 C15 H15 . . . 113.00 no
N3A C15 H15 . . . 113.00 no
C16 C15 H15 . . . 113.00 no
N3B C15 H15 . . . 98.00 no
C15 C16 H16 . . . 108.00 no
C18 C16 H16 . . . 109.00 no
C17 C16 H16 . . . 109.00 no
N2 C19 H19C . . . 109.00 no
N2 C19 H19B . . . 109.00 no
H19B C19 H19C . . . 109.00 no
H19A C19 H19B . . . 109.00 no
H19A C19 H19C . . . 110.00 no
N2 C19 H19A . . . 110.00 no
C22 C20 H20B . . . 109.00 no
H20A C20 H20B . . . 108.00 no
C9 C20 H20B . . . 108.00 no
C22 C20 H20A . . . 109.00 no
C9 C20 H20A . . . 109.00 no
C22 C21 H21A . . . 109.00 no
C22 C21 H21B . . . 109.00 no
H21B C21 H21C . . . 109.00 no
H21A C21 H21C . . . 110.00 no
H21A C21 H21B . . . 109.00 no
C22 C21 H21C . . . 109.00 no
C21 C22 H22A . . . 112.00 no
C20 C22 H22B . . . 105.00 no
C23A C22 H22B . . . 124.00 no
C21 C22 H22B . . . 105.00 no
C23A C22 H22A . . . 112.00 no
H22A C22 H22B . . . 13.00 no
C20 C22 H22A . . . 112.00 no
C23B C22 H22A . . . 86.00 no
C23B C22 H22B . . . 99.00 no
C22 C23A H23A . . . 110.00 no
C22 C23A H23B . . . 109.00 no
C22 C23A H23C . . . 110.00 no
C22 C23A H23D . . . 147.00 no
C23B C23A H23C . . . 77.00 no
C23B C23A H23D . . . 119.00 no
C23B C23A H23F . . . 44.00 no
H23A C23A H23B . . . 109.00 no
H23A C23A H23C . . . 109.00 no
H23A C23A H23D . . . 101.00 no
H23A C23A H23F . . . 33.00 no
H23B C23A H23C . . . 109.00 no
H23B C23A H23D . . . 70.00 no
H23B C23A H23F . . . 138.00 no
H23C C23A H23D . . . 47.00 no
H23C C23A H23F . . . 104.00 no
C22 C23A H23F . . . 82.00 no
C23B C23A H23A . . . 75.00 no
C23B C23A H23B . . . 169.00 no
H23D C23A H23F . . . 121.00 no
C22 C23B H23E . . . 110.00 no
C22 C23B H23F . . . 109.00 no
C22 C23B H23D . . . 109.00 no
C23A C23B H23C . . . 62.00 no
C23A C23B H23D . . . 20.00 no
C23A C23B H23A . . . 63.00 no
C23A C23B H23F . . . 105.00 no
H23A C23B H23C . . . 97.00 no
H23A C23B H23D . . . 66.00 no
H23A C23B H23E . . . 128.00 no
H23A C23B H23F . . . 43.00 no
H23C C23B H23D . . . 43.00 no
C23A C23B H23E . . . 128.00 no
H23C C23B H23F . . . 129.00 no
H23D C23B H23E . . . 109.00 no
H23D C23B H23F . . . 109.00 no
H23E C23B H23F . . . 109.00 no
H23C C23B H23E . . . 66.00 no
C22 C23B H23A . . . 121.00 no
C22 C23B H23C . . . 120.00 no
O5A C24A H24A . . . 110.00 no
O5A C24A H24B . . . 110.00 no
C25A C24A H24A . . . 110.00 no
C25A C24A H24B . . . 110.00 no
H24A C24A H24B . . . 109.00 no
O5B C24B H24C . . . 109.00 no
C25B C24B H24D . . . 108.00 no
O5B C24B H24D . . . 109.00 no
C25B C24B H24C . . . 109.00 no
H24C C24B H24D . . . 108.00 no
O6A C25A H25A . . . 110.00 no
O6A C25A H25B . . . 110.00 no
C24A C25A H25B . . . 110.00 no
H25A C25A H25B . . . 108.00 no
C24A C25A H25A . . . 110.00 no
O6B C25B H25C . . . 108.00 no
O6B C25B H25D . . . 108.00 no
C24B C25B H25C . . . 108.00 no
C24B C25B H25D . . . 109.00 no
H25C C25B H25D . . . 107.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C18 . . 1.350(10) no
F2 C18 . . 1.354(10) no
F3 C18 . . 1.349(9) no
F4 C17 . . 1.309(9) no
F5 C17 . . 1.362(10) no
F6 C17 . . 1.336(10) no
O1 C1 . . 1.341(8) no
O1 C4 . . 1.478(9) no
O2 C1 . . 1.212(9) no
O3 C8 . . 1.217(8) no
O4 C14 . . 1.244(9) no
O5A N3A . . 1.48(4) no
O5A C24A . . 1.47(2) no
O5B C24B . . 1.36(3) no
O5B N3B . . 1.45(4) no
O6A C25A . . 1.47(2) no
O6B C25B . . 1.43(3) no
O6A H6A1 . . 0.8400 no
O6B H6B1 . . 0.8400 no
N1 C8 . . 1.358(9) no
N1 C2 . . 1.443(9) no
N2 C19 . . 1.457(9) no
N2 C14 . . 1.342(9) no
N2 C9 . . 1.472(8) no
N3A C15 . . 1.46(3) no
N3B C15 . . 1.51(4) no
N1 H1N . . 0.88(5) no
N3A H3A1 . . 0.8800 no
N3B H3B1 . . 0.8800 no
C1 C2 . . 1.505(10) no
C2 C3 . . 1.526(11) no
C4 C6 . . 1.503(11) no
C4 C7 . . 1.523(10) no
C4 C5 . . 1.516(12) no
C8 C9 . . 1.554(9) no
C9 C20 . . 1.547(9) no
C14 C15 . . 1.548(9) no
C15 C16 . . 1.539(10) no
C16 C17 . . 1.524(10) no
C16 C18 . . 1.496(10) no
C20 C22 . . 1.501(11) no
C21 C22 . . 1.510(13) no
C22 C23B . . 1.413(19) no
C22 C23A . . 1.63(2) no
C23A C23B . . 0.73(2) no
C24A C25A . . 1.58(3) no
C24B C25B . . 1.50(3) no
C2 H2 . . 1.0000 no
C3 H3A . . 0.9800 no
C3 H3C . . 0.9800 no
C3 H3B . . 0.9800 no
C5 H5B . . 0.9800 no
C5 H5A . . 0.9800 no
C5 H5C . . 0.9800 no
C6 H6B . . 0.9800 no
C6 H6A . . 0.9800 no
C6 H6C . . 0.9800 no
C7 H7C . . 0.9800 no
C7 H7A . . 0.9800 no
C7 H7B . . 0.9800 no
C9 H9 . . 1.0000 no
C15 H15 . . 1.0000 no
C16 H16 . . 1.0000 no
C19 H19B . . 0.9800 no
C19 H19A . . 0.9800 no
C19 H19C . . 0.9800 no
C20 H20B . . 0.9900 no
C20 H20A . . 0.9900 no
C21 H21A . . 0.9800 no
C21 H21B . . 0.9800 no
C21 H21C . . 0.9800 no
C22 H22A . . 1.0000 no
C22 H22B . . 1.0000 no
C23A H23C . . 0.9800 no
C23A H23D . . 0.3900 no
C23A H23B . . 0.9800 no
C23A H23A . . 0.9800 no
C23A H23F . . 1.3600 no
C23B H23C . . 1.0800 no
C23B H23A . . 1.0600 no
C23B H23F . . 0.9800 no
C23B H23D . . 0.9800 no
C23B H23E . . 0.9800 no
C24A H24A . . 0.9900 no
C24A H24B . . 0.9900 no
C24B H24C . . 0.9900 no
C24B H24D . . 0.9900 no
C25A H25A . . 0.9900 no
C25A H25B . . 0.9900 no
C25B H25C . . 0.9900 no
C25B H25D . . 0.9900 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3A H3A1 F5 . 0.88 1.94 2.60(3) 130 yes
N1 H1N O2 . 0.88(5) 2.37(7) 2.720(9) 104(5) yes
N1 H1N O5A . 0.88(5) 2.38(6) 3.245(17) 169(6) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 O1 C1 O2 . . . . -4.5(11) no
C4 O1 C1 C2 . . . . 170.9(6) no
C1 O1 C4 C5 . . . . 62.9(8) no
C1 O1 C4 C6 . . . . -61.4(8) no
C1 O1 C4 C7 . . . . -176.9(6) no
C24A O5A N3A C15 . . . . 132.9(18) no
N3A O5A C24A C25A . . . . -72(2) no
C8 N1 C2 C1 . . . . -134.2(6) no
C8 N1 C2 C3 . . . . 104.4(7) no
C2 N1 C8 O3 . . . . 2.2(10) no
C2 N1 C8 C9 . . . . 178.7(6) no
C14 N2 C9 C8 . . . . -105.0(6) no
C14 N2 C9 C20 . . . . 128.2(6) no
C19 N2 C9 C8 . . . . 74.6(7) no
C19 N2 C9 C20 . . . . -52.3(8) no
C9 N2 C14 O4 . . . . -1.8(9) no
C9 N2 C14 C15 . . . . 173.6(5) no
C19 N2 C14 O4 . . . . 178.6(6) no
C19 N2 C14 C15 . . . . -6.0(9) no
O5A N3A C15 C14 . . . . 55.9(18) no
O5A N3A C15 C16 . . . . 171.0(14) no
O1 C1 C2 N1 . . . . 169.0(5) no
O1 C1 C2 C3 . . . . -69.6(7) no
O2 C1 C2 N1 . . . . -15.5(10) no
O2 C1 C2 C3 . . . . 105.8(8) no
O3 C8 C9 N2 . . . . -152.0(6) no
O3 C8 C9 C20 . . . . -24.6(8) no
N1 C8 C9 N2 . . . . 31.5(8) no
N1 C8 C9 C20 . . . . 158.8(6) no
N2 C9 C20 C22 . . . . -67.7(8) no
C8 C9 C20 C22 . . . . 165.1(6) no
O4 C14 C15 N3A . . . . 57.1(13) no
O4 C14 C15 C16 . . . . -51.5(8) no
N2 C14 C15 N3A . . . . -118.8(12) no
N2 C14 C15 C16 . . . . 132.6(6) no
N3A C15 C16 C17 . . . . 55.9(14) no
N3A C15 C16 C18 . . . . 177.7(13) no
C14 C15 C16 C17 . . . . 168.4(6) no
C14 C15 C16 C18 . . . . -69.9(8) no
C15 C16 C17 F4 . . . . 41.6(9) no
C15 C16 C17 F5 . . . . -79.4(8) no
C15 C16 C17 F6 . . . . 164.6(6) no
C18 C16 C17 F4 . . . . -80.8(8) no
C18 C16 C17 F5 . . . . 158.3(7) no
C18 C16 C17 F6 . . . . 42.3(9) no
C15 C16 C18 F1 . . . . -76.2(8) no
C15 C16 C18 F2 . . . . 161.9(6) no
C15 C16 C18 F3 . . . . 43.0(9) no
C17 C16 C18 F1 . . . . 47.0(9) no
C17 C16 C18 F2 . . . . -75.0(8) no
C17 C16 C18 F3 . . . . 166.2(7) no
C9 C20 C22 C21 . . . . 177.4(6) no
C9 C20 C22 C23A . . . . -67.8(9) no
C9 C20 C22 C23B . . . . -47.6(13) no
C20 C22 C23A C23B . . . . 140(2) no
C21 C22 C23A C23B . . . . -104(2) no
C20 C22 C23B C23A . . . . -49(2) no
C21 C22 C23B C23A . . . . 86(2) no
O5A C24A C25A O6A . . . . -60(2) no
