#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/71/2227169.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_2227169
loop_
_publ_author_name
'Simone, Michela I.'
'Edwards, Alison A.'
'Parker, Samuel G.'
'Tranter, George E.'
'Fleet, George W. J.'
'Watkin, David J.'
_publ_section_title
;
 Pentafluorophenyl
 (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate
;
_journal_coeditor_code           BH2308
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2699
_journal_page_last               o2700
_journal_paper_doi               10.1107/S1600536810038559
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H25 F5 N4 O9'
_chemical_formula_moiety         'C22 H25 F5 N4 O9'
_chemical_formula_sum            'C22 H25 F5 N4 O9'
_chemical_formula_weight         584.45
_chemical_melting_point          364.2
_chemical_name_systematic
;
Pentafluorophenyl
(3R,4R,5S)-5-{[(3R,4R,5S)-5-
azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-
dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 102.4436(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.8973(4)
_cell_length_b                   7.90700(10)
_cell_length_c                   24.7763(5)
_cell_measurement_reflns_used    4194
_cell_measurement_temperature    150
_cell_measurement_theta_max      25
_cell_measurement_theta_min      5
_cell_volume                     5145.56(14)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material
'CRYSTALS (Betteridge et al., 2003; Cooper et al., 2010)'
_computing_structure_refinement
'CRYSTALS (Betteridge et al., 2003; Cooper et al., 2010)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17175
_diffrn_reflns_theta_full        25.033
_diffrn_reflns_theta_max         25.033
_diffrn_reflns_theta_min         5.127
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2416.000
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.90
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9857
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     759
_refine_ls_number_reflns         4754
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.0002536
_refine_ls_shift/su_mean         0.0000339
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(F²) + (0.12P)² + 4.59P], where P=[max(Fo²,0) + 2Fc²]/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1592
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1592
_reflns_number_gt                4160
_reflns_number_total             4754
_reflns_threshold_expression     I>2.0σ(I)
_cod_data_source_file            bh2308.cif
_cod_data_source_block           I
_cod_original_cell_volume        5145.56(15)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2227169
_cod_database_fobs_code          2227169
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,y+1/2,z
-x,y,-z
-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_adp_type
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4720(2) 0.0750(9) 0.3805(2) 0.0420 Uani 1.0000 . .
O O2 0.44018(13) 0.1870(6) 0.34614(16) 0.0397 Uani 1.0000 . .
C C3 0.38899(19) 0.1640(8) 0.3421(2) 0.0393 Uani 1.0000 . .
C C4 0.35842(18) 0.2805(7) 0.2970(2) 0.0334 Uani 1.0000 . .
C C5 0.30354(19) 0.2195(8) 0.2792(3) 0.0406 Uani 1.0000 . .
O O6 0.27353(15) 0.3616(6) 0.2641(2) 0.0581 Uani 1.0000 . .
C C7 0.3045(2) 0.5121(7) 0.2749(2) 0.0386 Uani 1.0000 . .
C C8 0.35104(18) 0.4609(7) 0.3173(2) 0.0334 Uani 1.0000 . .
O O9 0.34056(13) 0.4538(6) 0.37104(15) 0.0449 Uani 1.0000 . .
C C10 0.3731(3) 0.5595(13) 0.4103(3) 0.0746 Uani 1.0000 . .
C C11 0.2724(2) 0.6557(8) 0.2890(3) 0.0440 Uani 1.0000 . .
N N12 0.23588(15) 0.7098(6) 0.2389(2) 0.0377 Uani 1.0000 . .
C C13 0.2519(2) 0.8066(7) 0.2025(3) 0.0418 Uani 1.0000 . .
C C14 0.21709(19) 0.8268(7) 0.1449(3) 0.0408 Uani 1.0000 . .
C C15 0.2357(2) 0.7039(8) 0.1041(2) 0.0396 Uani 1.0000 . .
O O16 0.27759(15) 0.6052(6) 0.13194(17) 0.0465 Uani 1.0000 . .
C C17 0.2760(5) 0.4357(10) 0.1194(5) 0.1005 Uani 1.0000 . .
C C18 0.2499(2) 0.8238(9) 0.0613(3) 0.0500 Uani 1.0000 . .
O O19 0.2628(2) 0.9862(7) 0.0925(2) 0.0662 Uani 1.0000 . .
C C20 0.2237(3) 1.0042(8) 0.1210(4) 0.0604 Uani 1.0000 . .
C C21 0.2956(3) 0.7817(11) 0.0418(3) 0.0663 Uani 1.0000 . .
N N22 0.3103(2) 0.9143(9) 0.0060(2) 0.0644 Uani 1.0000 . .
N N23 0.33914(17) 1.0349(8) 0.0317(2) 0.0455 Uani 1.0000 . .
N N24 0.3598(3) 1.1349(12) 0.0451(4) 0.0996 Uani 1.0000 . .
O O25 0.16578(14) 0.7812(6) 0.14434(18) 0.0475 Uani 1.0000 . .
C C26 0.1388(3) 0.9057(11) 0.1697(3) 0.0646 Uani 1.0000 . .
O O27 0.29382(14) 0.8802(6) 0.2127(2) 0.0511 Uani 1.0000 . .
O O28 0.38321(12) 0.3016(5) 0.25249(14) 0.0301 Uani 1.0000 . .
C C29 0.38704(19) 0.1522(8) 0.2206(2) 0.0367 Uani 1.0000 . .
O O30 0.37183(15) 0.0637(7) 0.3697(2) 0.0587 Uani 1.0000 . .
C C31 0.4741(3) -0.0927(9) 0.3682(3) 0.0514 Uani 1.0000 . .
C C32 0.5094(3) -0.1973(12) 0.4007(4) 0.0747 Uani 1.0000 . .
C C33 0.5434(3) -0.1318(14) 0.4461(3) 0.0724 Uani 1.0000 . .
C C34 0.5418(2) 0.0377(14) 0.4584(3) 0.0654 Uani 1.0000 . .
C C35 0.5070(2) 0.1392(11) 0.4262(3) 0.0514 Uani 1.0000 . .
F F36 0.50605(14) 0.3058(7) 0.43773(17) 0.0658 Uani 1.0000 . .
F F37 0.57451(14) 0.1043(9) 0.50139(17) 0.0893 Uani 1.0000 . .
F F38 0.5772(2) -0.2327(9) 0.4771(2) 0.1124 Uani 1.0000 . .
F F39 0.5108(3) -0.3608(7) 0.3887(3) 0.1051 Uani 1.0000 . .
F F40 0.44264(17) -0.1554(6) 0.32414(17) 0.0674 Uani 1.0000 . .
H H51 0.2930 0.1663 0.3101 0.0515 Uiso 1.0000 . .
H H52 0.2992 0.1399 0.2486 0.0513 Uiso 1.0000 . .
H H71 0.3164 0.5395 0.2409 0.0450 Uiso 1.0000 . .
H H81 0.3792 0.5329 0.3159 0.0414 Uiso 1.0000 . .
H H101 0.3618 0.5613 0.4445 0.1108 Uiso 1.0000 . .
H H102 0.4076 0.5171 0.4164 0.1109 Uiso 1.0000 . .
H H103 0.3719 0.6722 0.3955 0.1114 Uiso 1.0000 . .
H H111 0.2539 0.6184 0.3168 0.0536 Uiso 1.0000 . .
H H112 0.2937 0.7512 0.3025 0.0536 Uiso 1.0000 . .
H H151 0.2073 0.6292 0.0873 0.0484 Uiso 1.0000 . .
H H171 0.3063 0.3811 0.1416 0.1369 Uiso 1.0000 . .
H H172 0.2756 0.4218 0.0805 0.1373 Uiso 1.0000 . .
H H173 0.2452 0.3864 0.1274 0.1370 Uiso 1.0000 . .
H H181 0.2193 0.8517 0.0330 0.0616 Uiso 1.0000 . .
H H201 0.2328 1.0904 0.1501 0.0843 Uiso 1.0000 . .
H H202 0.1922 1.0373 0.0961 0.0842 Uiso 1.0000 . .
H H211 0.2902 0.6730 0.0219 0.0866 Uiso 1.0000 . .
H H212 0.3233 0.7699 0.0747 0.0861 Uiso 1.0000 . .
H H261 0.1043 0.8660 0.1674 0.1063 Uiso 1.0000 . .
H H262 0.1557 0.9180 0.2081 0.1062 Uiso 1.0000 . .
H H263 0.1385 1.0131 0.1508 0.1062 Uiso 1.0000 . .
H H291 0.4064 0.1752 0.1929 0.0577 Uiso 1.0000 . .
H H292 0.4042 0.0641 0.2445 0.0578 Uiso 1.0000 . .
H H293 0.3534 0.1133 0.2030 0.0571 Uiso 1.0000 . .
H H121 0.2049 0.6703 0.2314 0.0453 Uiso 1.0000 . .
C C117 0.5021(3) 0.2319(13) 0.0929(4) 0.0801 Uani 1.0000 . .
O O116 0.49194(18) 0.4042(8) 0.0831(2) 0.0722 Uani 1.0000 . .
C C115 0.4454(2) 0.4581(10) 0.0950(3) 0.0550 Uani 1.0000 . .
C C114 0.45486(17) 0.5879(7) 0.1427(2) 0.0310 Uani 1.0000 . .
C C120 0.4646(3) 0.7465(9) 0.1117(2) 0.0497 Uani 1.0000 . .
O O119 0.4268(2) 0.7415(9) 0.06111(19) 0.0794 Uani 1.0000 . .
C C118 0.4153(2) 0.5647(11) 0.0463(2) 0.0621 Uani 1.0000 . .
C C121 0.4308(5) 0.575(2) -0.0090(4) 0.0581 Uani 0.511(18) 1 1
N N122 0.3979(5) 0.6849(15) -0.0521(5) 0.0483 Uani 0.511(18) 1 1
N N123 0.4064(5) 0.8486(15) -0.0497(5) 0.0443 Uani 0.511(18) 1 1
N N124 0.4131(5) 0.9747(17) -0.0512(5) 0.0637 Uani 0.511(18) 1 1
C C113 0.49815(17) 0.5442(7) 0.1907(2) 0.0312 Uani 1.0000 . .
N N112 0.48531(14) 0.4574(6) 0.23224(18) 0.0337 Uani 1.0000 . .
C C111 0.5243(2) 0.3948(8) 0.2780(2) 0.0373 Uani 1.0000 . .
C C107 0.55076(18) 0.2409(7) 0.2601(2) 0.0312 Uani 1.0000 . .
O O106 0.51648(13) 0.0987(5) 0.25502(17) 0.0412 Uani 1.0000 . .
C C105 0.54569(18) -0.0488(8) 0.2533(2) 0.0372 Uani 1.0000 . .
C C104 0.60205(17) -0.0040(7) 0.2762(2) 0.0291 Uani 1.0000 . .
C C108 0.59836(18) 0.1781(7) 0.2994(2) 0.0320 Uani 1.0000 . .
O O109 0.59212(13) 0.1648(5) 0.35444(15) 0.0383 Uani 1.0000 . .
C C110 0.6201(2) 0.2895(9) 0.3900(2) 0.0492 Uani 1.0000 . .
C C103 0.62809(17) -0.1243(7) 0.3212(2) 0.0308 Uani 1.0000 . .
O O102 0.67965(12) -0.0920(5) 0.33282(14) 0.0312 Uani 1.0000 . .
C C101 0.71065(17) -0.1939(7) 0.3717(2) 0.0301 Uani 1.0000 . .
C C131 0.71597(19) -0.3638(7) 0.3636(2) 0.0333 Uani 1.0000 . .
C C132 0.7505(2) -0.4588(8) 0.4010(2) 0.0419 Uani 1.0000 . .
C C133 0.7793(2) -0.3825(8) 0.4467(2) 0.0398 Uani 1.0000 . .
C C134 0.7739(2) -0.2145(8) 0.4554(2) 0.0397 Uani 1.0000 . .
C C135 0.73976(19) -0.1191(7) 0.4179(2) 0.0337 Uani 1.0000 . .
F F136 0.73630(13) 0.0473(5) 0.42632(14) 0.0484 Uani 1.0000 . .
F F137 0.80219(14) -0.1370(6) 0.50043(14) 0.0575 Uani 1.0000 . .
F F138 0.81310(13) -0.4746(5) 0.48326(15) 0.0551 Uani 1.0000 . .
F F139 0.75578(15) -0.6241(5) 0.39232(16) 0.0559 Uani 1.0000 . .
F F140 0.68948(12) -0.4392(5) 0.31769(13) 0.0459 Uani 1.0000 . .
O O130 0.60865(14) -0.2288(5) 0.34484(17) 0.0434 Uani 1.0000 . .
O O128 0.63024(12) 0.0180(5) 0.23410(14) 0.0319 Uani 1.0000 . .
C C129 0.63836(19) -0.1350(8) 0.2052(2) 0.0382 Uani 1.0000 . .
O O127 0.54240(12) 0.5832(5) 0.19084(17) 0.0420 Uani 1.0000 . .
O O125 0.40702(12) 0.5920(5) 0.15871(14) 0.0350 Uani 1.0000 . .
C C126 0.3985(2) 0.7382(9) 0.1890(3) 0.0533 Uani 1.0000 . .
C C221 0.4201(5) 0.4784(19) -0.0043(4) 0.0622 Uani 0.489(18) 1 2
N N222 0.3914(4) 0.581(2) -0.0501(4) 0.0713 Uani 0.489(18) 1 2
N N223 0.4109(6) 0.730(3) -0.0551(7) 0.0682 Uani 0.489(18) 1 2
N N224 0.4213(7) 0.848(2) -0.0642(7) 0.0742 Uani 0.489(18) 1 2
H H1171 0.5378 0.2119 0.0944 0.1160 Uiso 1.0000 . .
H H1172 0.4817 0.1663 0.0638 0.1159 Uiso 1.0000 . .
H H1173 0.4944 0.2023 0.1280 0.1160 Uiso 1.0000 . .
H H1151 0.4263 0.3604 0.1032 0.0717 Uiso 1.0000 . .
H H1201 0.4993 0.7468 0.1062 0.0583 Uiso 1.0000 . .
H H1202 0.4591 0.8459 0.1319 0.0583 Uiso 1.0000 . .
H H1111 0.5084 0.3635 0.3083 0.0432 Uiso 1.0000 . .
H H1112 0.5502 0.4822 0.2899 0.0435 Uiso 1.0000 . .
H H1071 0.5596 0.2633 0.2239 0.0365 Uiso 1.0000 . .
H H1051 0.5413 -0.0905 0.2154 0.0461 Uiso 1.0000 . .
H H1052 0.5354 -0.1370 0.2760 0.0454 Uiso 1.0000 . .
H H1081 0.6282 0.2477 0.2973 0.0372 Uiso 1.0000 . .
H H1101 0.6117 0.2792 0.4257 0.0722 Uiso 1.0000 . .
H H1102 0.6113 0.4009 0.3753 0.0721 Uiso 1.0000 . .
H H1103 0.6556 0.2705 0.3940 0.0721 Uiso 1.0000 . .
H H1291 0.6531 -0.1053 0.1746 0.0582 Uiso 1.0000 . .
H H1292 0.6069 -0.1947 0.1926 0.0584 Uiso 1.0000 . .
H H1293 0.6617 -0.2071 0.2299 0.0583 Uiso 1.0000 . .
H H1261 0.3708 0.7169 0.2070 0.0804 Uiso 1.0000 . .
H H1262 0.3899 0.8332 0.1646 0.0800 Uiso 1.0000 . .
H H1263 0.4291 0.7634 0.2163 0.0800 Uiso 1.0000 . .
H H1121 0.4538 0.4325 0.2307 0.0413 Uiso 1.0000 . .
H H1211 0.4310 0.4576 -0.0243 0.0720 Uiso 0.511(18) 1 1
H H1212 0.4661 0.6221 -0.0016 0.0720 Uiso 0.511(18) 1 1
H H2211 0.4058 0.3615 -0.0054 0.0681 Uiso 0.489(18) 1 2
H H2212 0.4568 0.4724 -0.0061 0.0681 Uiso 0.489(18) 1 2
H H1181 0.3782 0.5463 0.0443 0.0747 Uiso 1.0000 . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 'International Tables Vol C 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
O2 C1 C31 . . . 122.2(6) no
O2 C1 C35 . . . 118.8(6) no
C31 C1 C35 . . . 118.6(6) no
C1 O2 C3 . . . 115.9(4) no
O2 C3 C4 . . . 110.1(4) no
O2 C3 O30 . . . 123.3(5) no
C4 C3 O30 . . . 126.6(5) no
C3 C4 C5 . . . 110.6(5) no
C3 C4 C8 . . . 113.7(4) no
C5 C4 C8 . . . 101.7(4) no
C3 C4 O28 . . . 111.6(4) no
C5 C4 O28 . . . 113.7(4) no
C8 C4 O28 . . . 105.1(4) no
C4 C5 O6 . . . 107.0(5) no
C4 C5 H51 . . . 109.8 no
O6 C5 H51 . . . 108.3 no
C4 C5 H52 . . . 112.0 no
O6 C5 H52 . . . 110.4 no
H51 C5 H52 . . . 109.2 no
C5 O6 C7 . . . 109.8(4) no
O6 C7 C8 . . . 105.5(5) no
O6 C7 C11 . . . 109.0(4) no
C8 C7 C11 . . . 118.0(5) no
O6 C7 H71 . . . 107.7 no
C8 C7 H71 . . . 106.3 no
C11 C7 H71 . . . 109.8 no
C4 C8 C7 . . . 99.6(4) no
C4 C8 O9 . . . 109.6(4) no
C7 C8 O9 . . . 111.3(4) no
C4 C8 H81 . . . 112.4 no
C7 C8 H81 . . . 111.1 no
O9 C8 H81 . . . 112.2 no
C8 O9 C10 . . . 113.5(5) no
O9 C10 H101 . . . 110.3 no
O9 C10 H102 . . . 109.3 no
H101 C10 H102 . . . 110.0 no
O9 C10 H103 . . . 108.5 no
H101 C10 H103 . . . 109.5 no
H102 C10 H103 . . . 109.3 no
C7 C11 N12 . . . 109.5(5) no
C7 C11 H111 . . . 109.8 no
N12 C11 H111 . . . 109.5 no
C7 C11 H112 . . . 110.0 no
N12 C11 H112 . . . 107.8 no
H111 C11 H112 . . . 110.2 no
C11 N12 C13 . . . 119.1(4) no
C11 N12 H121 . . . 120.7 no
C13 N12 H121 . . . 119.9 no
N12 C13 C14 . . . 118.0(5) no
N12 C13 O27 . . . 123.1(6) no
C14 C13 O27 . . . 118.9(5) no
C13 C14 C15 . . . 108.7(4) no
C13 C14 C20 . . . 110.6(5) no
C15 C14 C20 . . . 103.8(5) no
C13 C14 O25 . . . 112.2(4) no
C15 C14 O25 . . . 106.3(5) no
C20 C14 O25 . . . 114.6(5) no
C14 C15 O16 . . . 111.1(5) no
C14 C15 C18 . . . 103.0(5) no
O16 C15 C18 . . . 112.6(5) no
C14 C15 H151 . . . 108.8 no
O16 C15 H151 . . . 109.7 no
C18 C15 H151 . . . 111.4 no
C15 O16 C17 . . . 116.3(6) no
O16 C17 H171 . . . 108.8 no
O16 C17 H172 . . . 109.2 no
H171 C17 H172 . . . 109.7 no
O16 C17 H173 . . . 109.4 no
H171 C17 H173 . . . 110.6 no
H172 C17 H173 . . . 109.1 no
C15 C18 O19 . . . 103.8(5) no
C15 C18 C21 . . . 116.4(6) no
O19 C18 C21 . . . 104.4(6) no
C15 C18 H181 . . . 109.7 no
O19 C18 H181 . . . 103.9 no
C21 C18 H181 . . . 116.8 no
C18 O19 C20 . . . 103.4(5) no
C14 C20 O19 . . . 105.2(5) no
C14 C20 H201 . . . 112.3 no
O19 C20 H201 . . . 110.2 no
C14 C20 H202 . . . 109.4 no
O19 C20 H202 . . . 110.7 no
H201 C20 H202 . . . 109.0 no
C18 C21 N22 . . . 113.0(6) no
C18 C21 H211 . . . 108.8 no
N22 C21 H211 . . . 110.2 no
C18 C21 H212 . . . 106.9 no
N22 C21 H212 . . . 108.2 no
H211 C21 H212 . . . 109.7 no
C21 N22 N23 . . . 115.5(6) no
N22 N23 N24 . . . 170.6(8) no
C14 O25 C26 . . . 113.6(5) no
O25 C26 H261 . . . 108.5 no
O25 C26 H262 . . . 108.8 no
H261 C26 H262 . . . 109.5 no
O25 C26 H263 . . . 109.7 no
H261 C26 H263 . . . 110.5 no
H262 C26 H263 . . . 109.8 no
C4 O28 C29 . . . 115.7(4) no
O28 C29 H291 . . . 110.5 no
O28 C29 H292 . . . 109.7 no
H291 C29 H292 . . . 108.3 no
O28 C29 H293 . . . 109.8 no
H291 C29 H293 . . . 109.7 no
H292 C29 H293 . . . 108.9 no
C1 C31 C32 . . . 120.6(8) no
C1 C31 F40 . . . 119.8(6) no
C32 C31 F40 . . . 119.6(7) no
C31 C32 C33 . . . 120.0(9) no
C31 C32 F39 . . . 120.1(10) no
C33 C32 F39 . . . 119.9(8) no
C32 C33 C34 . . . 119.8(7) no
C32 C33 F38 . . . 119.8(10) no
C34 C33 F38 . . . 120.5(9) no
C33 C34 C35 . . . 119.7(8) no
C33 C34 F37 . . . 121.0(7) no
C35 C34 F37 . . . 119.3(9) no
C1 C35 C34 . . . 121.3(8) no
C1 C35 F36 . . . 119.0(6) no
C34 C35 F36 . . . 119.6(7) no
O116 C117 H1171 . . . 108.7 no
O116 C117 H1172 . . . 109.8 no
H1171 C117 H1172 . . . 110.1 no
O116 C117 H1173 . . . 108.7 no
H1171 C117 H1173 . . . 109.2 no
H1172 C117 H1173 . . . 110.4 no
C117 O116 C115 . . . 113.9(7) no
O116 C115 C114 . . . 110.7(4) no
O116 C115 C118 . . . 109.9(6) no
C114 C115 C118 . . . 101.9(6) no
O116 C115 H1151 . . . 109.7 no
C114 C115 H1151 . . . 111.9 no
C118 C115 H1151 . . . 112.6 no
C115 C114 C120 . . . 100.3(5) no
C115 C114 C113 . . . 114.9(5) no
C120 C114 C113 . . . 113.4(4) no
C115 C114 O125 . . . 102.7(4) no
C120 C114 O125 . . . 112.6(5) no
C113 C114 O125 . . . 111.9(4) no
C114 C120 O119 . . . 104.6(5) no
C114 C120 H1201 . . . 110.3 no
O119 C120 H1201 . . . 113.4 no
C114 C120 H1202 . . . 110.4 no
O119 C120 H1202 . . . 108.6 no
H1201 C120 H1202 . . . 109.4 no
C120 O119 C118 . . . 108.5(5) no
C115 C118 O119 . . . 106.2(5) no
C115 C118 C121 . . . 122.1(6) no
O119 C118 C121 . . . 95.3(8) no
C115 C118 H1181 . . . 108.0 no
O119 C118 H1181 . . . 108.0 no
C121 C118 H1181 . . . 115.2 no
C115 C118 O119 . . . 106.2(5) no
C115 C118 C221 . . . 106.6(8) no
O119 C118 C221 . . . 127.6(8) no
C115 C118 H1181 . . . 108.0 no
O119 C118 H1181 . . . 108.0 no
C221 C118 H1181 . . . 99.2 no
C118 C121 N122 . . . 115.8(7) no
C118 C121 H1211 . . . 108.7 no
N122 C121 H1211 . . . 108.5 no
C118 C121 H1212 . . . 106.7 no
N122 C121 H1212 . . . 107.5 no
H1211 C121 H1212 . . . 109.5 no
C121 N122 N123 . . . 118.0(8) no
N122 N123 N124 . . . 175.3(16) no
C114 C113 N112 . . . 115.9(4) no
C114 C113 O127 . . . 121.7(5) no
N112 C113 O127 . . . 122.4(5) no
C113 N112 C111 . . . 120.7(4) no
C113 N112 H1121 . . . 119.7 no
C111 N112 H1121 . . . 119.4 no
N112 C111 C107 . . . 110.3(4) no
N112 C111 H1111 . . . 109.1 no
C107 C111 H1111 . . . 109.4 no
N112 C111 H1112 . . . 109.9 no
C107 C111 H1112 . . . 107.7 no
H1111 C111 H1112 . . . 110.4 no
C111 C107 O106 . . . 108.5(4) no
C111 C107 C108 . . . 117.2(5) no
O106 C107 C108 . . . 103.7(4) no
C111 C107 H1071 . . . 109.9 no
O106 C107 H1071 . . . 109.5 no
C108 C107 H1071 . . . 107.8 no
C107 O106 C105 . . . 107.3(3) no
O106 C105 C104 . . . 108.0(4) no
O106 C105 H1051 . . . 110.7 no
C104 C105 H1051 . . . 109.6 no
O106 C105 H1052 . . . 110.2 no
C104 C105 H1052 . . . 109.4 no
H1051 C105 H1052 . . . 108.9 no
C105 C104 C108 . . . 102.2(4) no
C105 C104 C103 . . . 112.8(4) no
C108 C104 C103 . . . 111.3(4) no
C105 C104 O128 . . . 113.3(4) no
C108 C104 O128 . . . 104.1(4) no
C103 C104 O128 . . . 112.3(4) no
C104 C108 C107 . . . 100.2(4) no
C104 C108 O109 . . . 108.5(4) no
C107 C108 O109 . . . 112.6(4) no
C104 C108 H1081 . . . 112.3 no
C107 C108 H1081 . . . 111.6 no
O109 C108 H1081 . . . 111.1 no
C108 O109 C110 . . . 112.8(4) no
O109 C110 H1101 . . . 108.2 no
O109 C110 H1102 . . . 110.3 no
H1101 C110 H1102 . . . 109.7 no
O109 C110 H1103 . . . 109.9 no
H1101 C110 H1103 . . . 108.6 no
H1102 C110 H1103 . . . 110.1 no
C104 C103 O102 . . . 108.8(4) no
C104 C103 O130 . . . 127.7(4) no
O102 C103 O130 . . . 123.5(5) no
C103 O102 C101 . . . 117.7(4) no
O102 C101 C131 . . . 122.3(5) no
O102 C101 C135 . . . 118.5(5) no
C131 C101 C135 . . . 119.1(5) no
C101 C131 C132 . . . 120.7(5) no
C101 C131 F140 . . . 120.4(5) no
C132 C131 F140 . . . 118.9(5) no
C131 C132 C133 . . . 119.6(5) no
C131 C132 F139 . . . 120.1(6) no
C133 C132 F139 . . . 120.3(5) no
C132 C133 C134 . . . 120.1(5) no
C132 C133 F138 . . . 119.8(5) no
C134 C133 F138 . . . 120.1(6) no
C133 C134 C135 . . . 120.4(6) no
C133 C134 F137 . . . 120.8(5) no
C135 C134 F137 . . . 118.8(6) no
C134 C135 C101 . . . 120.1(5) no
C134 C135 F136 . . . 119.3(5) no
C101 C135 F136 . . . 120.5(5) no
C104 O128 C129 . . . 114.9(4) no
O128 C129 H1291 . . . 108.6 no
O128 C129 H1292 . . . 110.8 no
H1291 C129 H1292 . . . 110.4 no
O128 C129 H1293 . . . 109.1 no
H1291 C129 H1293 . . . 109.0 no
H1292 C129 H1293 . . . 108.9 no
C114 O125 C126 . . . 115.0(4) no
O125 C126 H1261 . . . 109.3 no
O125 C126 H1262 . . . 110.3 no
H1261 C126 H1262 . . . 108.8 no
O125 C126 H1263 . . . 109.1 no
H1261 C126 H1263 . . . 109.8 no
H1262 C126 H1263 . . . 109.4 no
C118 C221 N222 . . . 106.0(7) no
C118 C221 H2211 . . . 110.6 no
N222 C221 H2211 . . . 110.7 no
C118 C221 H2212 . . . 109.4 no
N222 C221 H2212 . . . 110.5 no
H2211 C221 H2212 . . . 109.5 no
C221 N222 N223 . . . 114.5(8) no
N222 N223 N224 . . . 170.8(17) 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
C1 O2 . . 1.388(7) no
C1 C31 . . 1.365(10) no
C1 C35 . . 1.401(10) no
O2 C3 . . 1.371(6) no
C3 C4 . . 1.542(8) no
C3 O30 . . 1.202(7) no
C4 C5 . . 1.525(7) no
C4 C8 . . 1.540(8) no
C4 O28 . . 1.416(6) no
C5 O6 . . 1.387(7) no
C5 H51 . . 0.966 no
C5 H52 . . 0.973 no
O6 C7 . . 1.444(7) no
C7 C8 . . 1.507(7) no
C7 C11 . . 1.512(8) no
C7 H71 . . 0.986 no
C8 O9 . . 1.420(6) no
C8 H81 . . 0.954 no
O9 C10 . . 1.429(8) no
C10 H101 . . 0.959 no
C10 H102 . . 0.968 no
C10 H103 . . 0.962 no
C11 N12 . . 1.471(8) no
C11 H111 . . 0.979 no
C11 H112 . . 0.963 no
N12 C13 . . 1.324(8) no
N12 H121 . . 0.870 no
C13 C14 . . 1.538(9) no
C13 O27 . . 1.245(7) no
C14 C15 . . 1.559(8) no
C14 C20 . . 1.546(8) no
C14 O25 . . 1.424(6) no
C15 O16 . . 1.422(7) no
C15 C18 . . 1.531(9) no
C15 H151 . . 0.983 no
O16 C17 . . 1.374(9) no
C17 H171 . . 0.980 no
C17 H172 . . 0.969 no
C17 H173 . . 0.972 no
C18 O19 . . 1.500(9) no
C18 C21 . . 1.453(9) no
C18 H181 . . 0.985 no
O19 C20 . . 1.397(8) no
C20 H201 . . 0.984 no
C20 H202 . . 0.970 no
C21 N22 . . 1.482(9) no
C21 H211 . . 0.986 no
C21 H212 . . 0.982 no
N22 N23 . . 1.305(8) no
N23 N24 . . 0.983(9) no
O25 C26 . . 1.446(9) no
C26 H261 . . 0.968 no
C26 H262 . . 0.967 no
C26 H263 . . 0.969 no
O28 C29 . . 1.438(7) no
C29 H291 . . 0.962 no
C29 H292 . . 0.965 no
C29 H293 . . 0.967 no
C31 C32 . . 1.379(10) no
C31 F40 . . 1.325(9) no
C32 C33 . . 1.388(14) no
C32 F39 . . 1.329(12) no
C33 C34 . . 1.377(14) no
C33 F38 . . 1.323(9) no
C34 C35 . . 1.356(10) no
C34 F37 . . 1.335(10) no
C35 F36 . . 1.350(9) no
C117 O116 . . 1.400(12) no
C117 H1171 . . 0.967 no
C117 H1172 . . 0.958 no
C117 H1173 . . 0.967 no
O116 C115 . . 1.411(7) no
C115 C114 . . 1.545(8) no
C115 C118 . . 1.548(11) no
C115 H1151 . . 0.973 no
C114 C120 . . 1.523(8) no
C114 C113 . . 1.514(7) no
C114 O125 . . 1.426(5) no
C120 O119 . . 1.434(7) no
C120 H1201 . . 0.971 no
C120 H1202 . . 0.960 no
O119 C118 . . 1.461(11) no
C118 C121 . . 1.519(8) no
C118 H1181 . . 1.000 no
C118 C221 . . 1.458(8) no
C118 H1181 . . 1.000 no
C121 N122 . . 1.508(9) no
C121 H1211 . . 1.000 no
C121 H1212 . . 1.000 no
N122 N123 . . 1.313(9) no
N123 N124 . . 1.015(9) no
C113 N112 . . 1.343(7) no
C113 O127 . . 1.229(6) no
N112 C111 . . 1.455(7) no
N112 H1121 . . 0.863 no
C111 C107 . . 1.524(7) no
C111 H1111 . . 0.971 no
C111 H1112 . . 0.981 no
C107 O106 . . 1.442(7) no
C107 C108 . . 1.515(7) no
C107 H1071 . . 0.992 no
O106 C105 . . 1.412(7) no
C105 C104 . . 1.541(6) no
C105 H1051 . . 0.979 no
C105 H1052 . . 0.973 no
C104 C108 . . 1.562(7) no
C104 C103 . . 1.518(7) no
C104 O128 . . 1.425(6) no
C108 O109 . . 1.414(6) no
C108 H1081 . . 0.983 no
O109 C110 . . 1.424(7) no
C110 H1101 . . 0.963 no
C110 H1102 . . 0.962 no
C110 H1103 . . 0.952 no
C103 O102 . . 1.378(6) no
C103 O130 . . 1.196(6) no
O102 C101 . . 1.387(6) no
C101 C131 . . 1.370(8) no
C101 C135 . . 1.374(8) no
C131 C132 . . 1.385(8) no
C131 F140 . . 1.344(6) no
C132 C133 . . 1.366(9) no
C132 F139 . . 1.337(7) no
C133 C134 . . 1.359(9) no
C133 F138 . . 1.350(6) no
C134 C135 . . 1.382(8) no
C134 F137 . . 1.354(7) no
C135 F136 . . 1.339(7) no
O128 C129 . . 1.446(7) no
C129 H1291 . . 0.958 no
C129 H1292 . . 0.961 no
C129 H1293 . . 0.963 no
O125 C126 . . 1.423(8) no
C126 H1261 . . 0.963 no
C126 H1262 . . 0.961 no
C126 H1263 . . 0.967 no
C221 N222 . . 1.474(9) no
C221 H2211 . . 1.000 no
C221 H2212 . . 1.000 no
N222 N223 . . 1.301(9) no
N223 N224 . . 1.014(9) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
C5 H52 O27 . . 1_545 0.97 2.23 3.131(10) 153 yes
C20 H202 N222 . . 4_555 0.97 2.32 3.269(10) 167 yes
C26 H263 N222 . . 4_555 0.97 2.51 3.214(10) 129 yes
C29 H293 O27 . . 1_545 0.97 2.49 3.278(10) 139 yes
N12 H121 O128 . . 2_455 0.87 2.36 3.200(10) 164 yes
C129 H1292 O127 . . 1_545 0.96 2.46 3.370(10) 158 yes
C126 H1261 O27 . . . 0.96 2.47 3.202(10) 133 yes
N112 H1121 O28 . . . 0.86 2.33 3.147(10) 159 yes
