#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:25:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180298 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/12/7151257.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_7151257
loop_
_publ_author_name
'Hayman, Colin M.'
'Larsen, David S.'
'Simpson, Jim'
'Bailey, Karl B.'
'Gill, Gurmit Singh'
_publ_section_title
;
 A stereoselective synthesis of 6,6,6-trifluoro-L-daunosamine and
 6,6,6-trifluoro-L-acosamine.
;
_journal_issue                   14
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2794
_journal_page_last               2800
_journal_paper_doi               10.1039/b606055b
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_formula_sum            'C18 H21 F6 N O4'
_chemical_formula_weight         429.36
_chemical_name_systematic
;
N-(6-ethoxy-3-hydroxy-2-(trifluoromethyl)-tetrahydro-2H-pyran-4-yl)-
2,2,2-trifluoro-N-(1-phenylethyl)acetamide
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.345(3)
_cell_angle_beta                 98.080(3)
_cell_angle_gamma                103.188(3)
_cell_formula_units_Z            2
_cell_length_a                   9.499(2)
_cell_length_b                   10.601(3)
_cell_length_c                   11.958(3)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      8.64
_cell_volume                     1039.9(5)
_computing_cell_refinement       'SAINT (Bruker 1999)'
_computing_data_collection       'SMART (Bruker 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) & PLATON (Spek 1995)
;
_computing_publication_material
;
SHELXL-97 & enCIFER V1.1 (Allen et al., 2004)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, 1997) & TITAN2000 (Hunter & Simpson, 1999)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'φ and 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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13093
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.68
_diffrn_reflns_theta_min         2.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Friedel pairs were averaged'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         4459
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0577P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                3981
_reflns_number_total             4459
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b606055b.txt
_cod_data_source_block           feda
_cod_original_cell_volume        1039.9(4)
_cod_database_code               7151257
loop_
_symmetry_equiv_pos_as_xyz
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C12' C 1.4283(4) 1.1903(3) 0.4805(3) 0.0708(8) Uani 1 1 d . . .
H12A H 1.4459 1.1098 0.4170 0.106 Uiso 1 1 calc R . .
H12B H 1.4899 1.2789 0.4855 0.106 Uiso 1 1 calc R . .
H12C H 1.3248 1.1840 0.4590 0.106 Uiso 1 1 calc R . .
C11' C 1.4662(3) 1.1878(3) 0.6056(3) 0.0530(6) Uani 1 1 d . . .
H11A H 1.5709 1.1948 0.6282 0.064 Uiso 1 1 calc R . .
H11B H 1.4495 1.2694 0.6704 0.064 Uiso 1 1 calc R . .
O11 O 1.37320(17) 1.05468(17) 0.59702(16) 0.0461(4) Uani 1 1 d . . .
C11 C 1.4225(2) 1.0231(2) 0.6948(2) 0.0373(4) Uani 1 1 d . . .
H11 H 1.5281 1.0282 0.7035 0.045 Uiso 1 1 calc R . .
C12 C 1.3288(2) 0.8730(2) 0.6681(2) 0.0366(4) Uani 1 1 d . . .
H12D H 1.3386 0.8018 0.5905 0.044 Uiso 1 1 calc R . .
H12E H 1.2241 0.8675 0.6584 0.044 Uiso 1 1 calc R . .
C13 C 1.3833(2) 0.8419(2) 0.77854(19) 0.0328(4) Uani 1 1 d . . .
H13 H 1.4865 0.8415 0.7795 0.039 Uiso 1 1 calc R . .
N13 N 1.29754(18) 0.69448(18) 0.76010(16) 0.0347(4) Uani 1 1 d . . .
C115 C 1.1535(2) 0.6690(2) 0.7641(2) 0.0403(5) Uani 1 1 d . . .
O115 O 1.08372(16) 0.75550(17) 0.77818(16) 0.0455(4) Uani 1 1 d . . .
C116 C 1.0646(3) 0.5160(3) 0.7479(3) 0.0538(6) Uani 1 1 d . . .
F164 F 0.9310(2) 0.5180(2) 0.7687(2) 0.0851(6) Uani 1 1 d . . .
F165 F 1.1332(2) 0.4778(2) 0.82870(17) 0.0754(5) Uani 1 1 d . . .
F166 F 1.04072(16) 0.41339(15) 0.63171(15) 0.0596(4) Uani 1 1 d . . .
C17 C 1.3792(2) 0.5837(2) 0.7320(2) 0.0406(5) Uani 1 1 d . . .
H17 H 1.3047 0.4897 0.7057 0.049 Uiso 1 1 calc R . .
C114 C 1.4925(3) 0.6139(3) 0.8507(2) 0.0536(6) Uani 1 1 d . . .
H11C H 1.5639 0.7082 0.8823 0.080 Uiso 1 1 calc R . .
H11D H 1.5435 0.5425 0.8309 0.080 Uiso 1 1 calc R . .
H11E H 1.4413 0.6100 0.9136 0.080 Uiso 1 1 calc R . .
C18 C 1.4415(2) 0.5757(2) 0.6205(2) 0.0386(5) Uani 1 1 d . . .
C19 C 1.3433(2) 0.5090(2) 0.5003(2) 0.0411(5) Uani 1 1 d . . .
H19 H 1.2418 0.4682 0.4900 0.049 Uiso 1 1 calc R . .
C110 C 1.3955(3) 0.5029(3) 0.3965(2) 0.0528(6) Uani 1 1 d . . .
H110 H 1.3292 0.4586 0.3170 0.063 Uiso 1 1 calc R . .
C111 C 1.5469(4) 0.5630(4) 0.4113(3) 0.0745(9) Uani 1 1 d . . .
H111 H 1.5824 0.5579 0.3415 0.089 Uiso 1 1 calc R . .
C112 C 1.6446(3) 0.6303(4) 0.5298(3) 0.0827(11) Uani 1 1 d . . .
H112 H 1.7456 0.6727 0.5398 0.099 Uiso 1 1 calc R . .
C113 C 1.5937(3) 0.6352(3) 0.6336(3) 0.0593(7) Uani 1 1 d . . .
H113 H 1.6609 0.6784 0.7126 0.071 Uiso 1 1 calc R . .
C14 C 1.3905(2) 0.9607(2) 0.90685(19) 0.0361(4) Uani 1 1 d . . .
H14 H 1.2892 0.9554 0.9174 0.043 Uiso 1 1 calc R . .
O14 O 1.47505(17) 0.94022(19) 1.00262(14) 0.0440(4) Uani 1 1 d . . .
H14A H 1.4275 0.9396 1.0547 0.066 Uiso 1 1 calc R . .
C15 C 1.4688(2) 1.1091(2) 0.9139(2) 0.0390(5) Uani 1 1 d . . .
H15 H 1.5747 1.1189 0.9178 0.047 Uiso 1 1 calc R . .
C16 C 1.4577(3) 1.2339(3) 1.0286(2) 0.0502(6) Uani 1 1 d . . .
F161 F 1.5162(2) 1.36102(16) 1.02762(19) 0.0788(6) Uani 1 1 d . . .
F162 F 1.31809(16) 1.22358(17) 1.03650(16) 0.0637(4) Uani 1 1 d . . .
F163 F 1.5333(2) 1.2414(2) 1.13579(15) 0.0798(6) Uani 1 1 d . . .
O15 O 1.40525(16) 1.12704(15) 0.80891(15) 0.0410(3) Uani 1 1 d . . .
C22' C 0.9831(3) 0.5826(3) 0.4147(2) 0.0468(5) Uani 1 1 d . . .
H22A H 0.9882 0.5718 0.4910 0.070 Uiso 1 1 calc R . .
H22B H 0.9249 0.6454 0.4136 0.070 Uiso 1 1 calc R . .
H22C H 1.0823 0.6235 0.4107 0.070 Uiso 1 1 calc R . .
C21' C 0.9115(3) 0.4386(2) 0.3043(2) 0.0454(5) Uani 1 1 d . . .
H21A H 0.8118 0.3953 0.3082 0.054 Uiso 1 1 calc R . .
H21B H 0.9036 0.4483 0.2266 0.054 Uiso 1 1 calc R . .
O21 O 1.00458(15) 0.34940(15) 0.30869(14) 0.0366(3) Uani 1 1 d . . .
C21 C 0.9432(2) 0.2073(2) 0.21894(18) 0.0314(4) Uani 1 1 d . . .
H21 H 0.8389 0.1698 0.2191 0.038 Uiso 1 1 calc R . .
C22 C 1.0342(2) 0.1182(2) 0.24781(18) 0.0317(4) Uani 1 1 d . . .
H22D H 1.0308 0.1214 0.3296 0.038 Uiso 1 1 calc R . .
H22E H 1.1378 0.1564 0.2492 0.038 Uiso 1 1 calc R . .
C23 C 0.9667(2) -0.0367(2) 0.14503(18) 0.0284(4) Uani 1 1 d . . .
H23 H 0.8618 -0.0670 0.1465 0.034 Uiso 1 1 calc R . .
N23 N 1.03464(17) -0.13945(17) 0.17020(15) 0.0305(3) Uani 1 1 d . . .
C215 C 1.1756(2) -0.1317(2) 0.16195(18) 0.0339(4) Uani 1 1 d . . .
O215 O 1.25656(16) -0.04392(18) 0.13679(15) 0.0416(3) Uani 1 1 d . . .
C216 C 1.2428(3) -0.2444(3) 0.1833(2) 0.0456(5) Uani 1 1 d . . .
F264 F 1.37429(17) -0.2320(2) 0.15481(18) 0.0697(5) Uani 1 1 d . . .
F265 F 1.15559(19) -0.38026(17) 0.11416(16) 0.0635(4) Uani 1 1 d . . .
F266 F 1.26914(16) -0.22070(17) 0.30434(14) 0.0548(4) Uani 1 1 d . . .
C27 C 0.9398(2) -0.2379(2) 0.2119(2) 0.0353(4) Uani 1 1 d . . .
H27 H 1.0035 -0.2863 0.2396 0.042 Uiso 1 1 calc R . .
C214 C 0.8118(3) -0.3551(3) 0.1024(3) 0.0494(6) Uani 1 1 d . . .
H21C H 0.7511 -0.3111 0.0685 0.074 Uiso 1 1 calc R . .
H21D H 0.7520 -0.4155 0.1316 0.074 Uiso 1 1 calc R . .
H21E H 0.8516 -0.4126 0.0381 0.074 Uiso 1 1 calc R . .
C28 C 0.8948(2) -0.1458(2) 0.3263(2) 0.0361(4) Uani 1 1 d . . .
C29 C 1.0051(2) -0.0612(2) 0.4400(2) 0.0390(5) Uani 1 1 d . . .
H29 H 1.1023 -0.0655 0.4444 0.047 Uiso 1 1 calc R . .
C210 C 0.9716(3) 0.0284(3) 0.5459(2) 0.0521(6) Uani 1 1 d . . .
H210 H 1.0458 0.0842 0.6210 0.063 Uiso 1 1 calc R . .
C211 C 0.8280(4) 0.0350(4) 0.5399(3) 0.0674(9) Uani 1 1 d . . .
H211 H 0.8057 0.0964 0.6109 0.081 Uiso 1 1 calc R . .
C212 C 0.7171(3) -0.0485(4) 0.4297(3) 0.0716(9) Uani 1 1 d . . .
H212 H 0.6202 -0.0439 0.4269 0.086 Uiso 1 1 calc R . .
C213 C 0.7488(3) -0.1396(3) 0.3225(3) 0.0526(6) Uani 1 1 d . . .
H213 H 0.6732 -0.1964 0.2484 0.063 Uiso 1 1 calc R . .
C24 C 0.9637(2) -0.0444(2) 0.01345(18) 0.0300(4) Uani 1 1 d . . .
H24 H 1.0658 -0.0179 0.0044 0.036 Uiso 1 1 calc R . .
O24 O 0.88139(15) -0.18639(16) -0.07856(13) 0.0371(3) Uani 1 1 d . . .
H24A H 0.9316 -0.2173 -0.1273 0.056 Uiso 1 1 calc R . .
C25 C 0.8833(2) 0.0626(2) 0.00015(18) 0.0319(4) Uani 1 1 d . . .
H25 H 0.7784 0.0281 0.0002 0.038 Uiso 1 1 calc R . .
C26 C 0.8895(2) 0.0790(3) -0.1208(2) 0.0398(5) Uani 1 1 d . . .
F261 F 0.83656(16) 0.18527(17) -0.12311(14) 0.0533(4) Uani 1 1 d . . .
F262 F 1.02726(15) 0.1089(2) -0.13530(14) 0.0600(4) Uani 1 1 d . . .
F263 F 0.80340(19) -0.04057(18) -0.22182(13) 0.0637(4) Uani 1 1 d . . .
O25 O 0.95007(15) 0.20367(15) 0.09834(13) 0.0340(3) 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
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 . . ?
O11 C11' C12' 109.0(2) . . ?
O11 C11' H11A 109.9 . . ?
C12' C11' H11A 109.9 . . ?
O11 C11' H11B 109.9 . . ?
C12' C11' H11B 109.9 . . ?
H11A C11' H11B 108.3 . . ?
C11 O11 C11' 113.99(17) . . ?
O11 C11 O15 108.39(17) . . ?
O11 C11 C12 109.61(17) . . ?
O15 C11 C12 109.19(17) . . ?
O11 C11 H11 109.9 . . ?
O15 C11 H11 109.9 . . ?
C12 C11 H11 109.9 . . ?
C11 C12 C13 108.63(16) . . ?
C11 C12 H12D 110.0 . . ?
C13 C12 H12D 110.0 . . ?
C11 C12 H12E 110.0 . . ?
C13 C12 H12E 110.0 . . ?
H12D C12 H12E 108.3 . . ?
N13 C13 C14 112.14(17) . . ?
N13 C13 C12 112.53(15) . . ?
C14 C13 C12 113.05(17) . . ?
N13 C13 H13 106.2 . . ?
C14 C13 H13 106.2 . . ?
C12 C13 H13 106.2 . . ?
C115 N13 C13 118.34(17) . . ?
C115 N13 C17 125.04(18) . . ?
C13 N13 C17 116.55(16) . . ?
O115 C115 N13 125.3(2) . . ?
O115 C115 C116 116.2(2) . . ?
N13 C115 C116 118.4(2) . . ?
F166 C116 F164 107.0(2) . . ?
F166 C116 F165 108.4(2) . . ?
F164 C116 F165 107.6(2) . . ?
F166 C116 C115 112.0(2) . . ?
F164 C116 C115 109.0(2) . . ?
F165 C116 C115 112.6(2) . . ?
N13 C17 C18 108.44(17) . . ?
N13 C17 C114 110.71(18) . . ?
C18 C17 C114 115.8(2) . . ?
N13 C17 H17 107.2 . . ?
C18 C17 H17 107.2 . . ?
C114 C17 H17 107.2 . . ?
C17 C114 H11C 109.5 . . ?
C17 C114 H11D 109.5 . . ?
H11C C114 H11D 109.5 . . ?
C17 C114 H11E 109.5 . . ?
H11C C114 H11E 109.5 . . ?
H11D C114 H11E 109.5 . . ?
C19 C18 C113 118.6(2) . . ?
C19 C18 C17 119.0(2) . . ?
C113 C18 C17 122.3(2) . . ?
C110 C19 C18 120.7(2) . . ?
C110 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C110 C111 120.0(3) . . ?
C19 C110 H110 120.0 . . ?
C111 C110 H110 120.0 . . ?
C112 C111 C110 119.8(3) . . ?
C112 C111 H111 120.1 . . ?
C110 C111 H111 120.1 . . ?
C113 C112 C111 120.6(3) . . ?
C113 C112 H112 119.7 . . ?
C111 C112 H112 119.7 . . ?
C112 C113 C18 120.3(3) . . ?
C112 C113 H113 119.8 . . ?
C18 C113 H113 119.8 . . ?
O14 C14 C13 108.40(16) . . ?
O14 C14 C15 109.58(16) . . ?
C13 C14 C15 108.85(17) . . ?
O14 C14 H14 110.0 . . ?
C13 C14 H14 110.0 . . ?
C15 C14 H14 110.0 . . ?
C14 O14 H14A 109.5 . . ?
O15 C15 C16 105.27(19) . . ?
O15 C15 C14 112.73(16) . . ?
C16 C15 C14 112.32(19) . . ?
O15 C15 H15 108.8 . . ?
C16 C15 H15 108.8 . . ?
C14 C15 H15 108.8 . . ?
F162 C16 F161 107.2(2) . . ?
F162 C16 F163 106.8(2) . . ?
F161 C16 F163 106.90(19) . . ?
F162 C16 C15 113.09(17) . . ?
F161 C16 C15 111.3(2) . . ?
F163 C16 C15 111.2(2) . . ?
C15 O15 C11 110.58(15) . . ?
C21' C22' H22A 109.5 . . ?
C21' C22' H22B 109.5 . . ?
H22A C22' H22B 109.5 . . ?
C21' C22' H22C 109.5 . . ?
H22A C22' H22C 109.5 . . ?
H22B C22' H22C 109.5 . . ?
O21 C21' C22' 107.35(17) . . ?
O21 C21' H21A 110.2 . . ?
C22' C21' H21A 110.2 . . ?
O21 C21' H21B 110.2 . . ?
C22' C21' H21B 110.2 . . ?
H21A C21' H21B 108.5 . . ?
C21 O21 C21' 113.58(15) . . ?
O21 C21 O25 107.58(15) . . ?
O21 C21 C22 109.00(15) . . ?
O25 C21 C22 109.95(16) . . ?
O21 C21 H21 110.1 . . ?
O25 C21 H21 110.1 . . ?
C22 C21 H21 110.1 . . ?
C21 C22 C23 107.70(15) . . ?
C21 C22 H22D 110.2 . . ?
C23 C22 H22D 110.2 . . ?
C21 C22 H22E 110.2 . . ?
C23 C22 H22E 110.2 . . ?
H22D C22 H22E 108.5 . . ?
N23 C23 C22 113.14(15) . . ?
N23 C23 C24 113.73(16) . . ?
C22 C23 C24 111.40(15) . . ?
N23 C23 H23 105.9 . . ?
C22 C23 H23 105.9 . . ?
C24 C23 H23 105.9 . . ?
C215 N23 C23 118.86(16) . . ?
C215 N23 C27 125.38(16) . . ?
C23 N23 C27 115.62(15) . . ?
O215 C215 N23 125.21(18) . . ?
O215 C215 C216 116.63(18) . . ?
N23 C215 C216 118.16(18) . . ?
F265 C216 F264 108.2(2) . . ?
F265 C216 F266 107.3(2) . . ?
F264 C216 F266 106.57(18) . . ?
F265 C216 C215 113.36(18) . . ?
F264 C216 C215 109.23(19) . . ?
F266 C216 C215 111.86(19) . . ?
N23 C27 C28 108.50(16) . . ?
N23 C27 C214 110.98(18) . . ?
C28 C27 C214 115.64(18) . . ?
N23 C27 H27 107.1 . . ?
C28 C27 H27 107.1 . . ?
C214 C27 H27 107.1 . . ?
C27 C214 H21C 109.5 . . ?
C27 C214 H21D 109.5 . . ?
H21C C214 H21D 109.5 . . ?
C27 C214 H21E 109.5 . . ?
H21C C214 H21E 109.5 . . ?
H21D C214 H21E 109.5 . . ?
C213 C28 C29 118.6(2) . . ?
C213 C28 C27 123.0(2) . . ?
C29 C28 C27 118.39(18) . . ?
C210 C29 C28 120.9(2) . . ?
C210 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C211 C210 C29 119.8(3) . . ?
C211 C210 H210 120.1 . . ?
C29 C210 H210 120.1 . . ?
C210 C211 C212 120.4(3) . . ?
C210 C211 H211 119.8 . . ?
C212 C211 H211 119.8 . . ?
C211 C212 C213 120.5(3) . . ?
C211 C212 H212 119.8 . . ?
C213 C212 H212 119.8 . . ?
C212 C213 C28 119.8(3) . . ?
C212 C213 H213 120.1 . . ?
C28 C213 H213 120.1 . . ?
O24 C24 C23 108.82(15) . . ?
O24 C24 C25 109.49(14) . . ?
C23 C24 C25 107.18(15) . . ?
O24 C24 H24 110.4 . . ?
C23 C24 H24 110.4 . . ?
C25 C24 H24 110.4 . . ?
C24 O24 H24A 109.5 . . ?
O25 C25 C26 104.82(16) . . ?
O25 C25 C24 112.32(14) . . ?
C26 C25 C24 112.41(17) . . ?
O25 C25 H25 109.1 . . ?
C26 C25 H25 109.1 . . ?
C24 C25 H25 109.1 . . ?
F262 C26 F263 108.5(2) . . ?
F262 C26 F261 107.03(18) . . ?
F263 C26 F261 105.63(16) . . ?
F262 C26 C25 112.82(16) . . ?
F263 C26 C25 110.98(18) . . ?
F261 C26 C25 111.59(19) . . ?
C25 O25 C21 111.30(14) . . ?
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
C12' C11' 1.502(4) . ?
C12' H12A 0.9600 . ?
C12' H12B 0.9600 . ?
C12' H12C 0.9600 . ?
C11' O11 1.440(3) . ?
C11' H11A 0.9700 . ?
C11' H11B 0.9700 . ?
O11 C11 1.387(3) . ?
C11 O15 1.434(3) . ?
C11 C12 1.517(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.534(3) . ?
C12 H12D 0.9700 . ?
C12 H12E 0.9700 . ?
C13 N13 1.500(3) . ?
C13 C14 1.531(3) . ?
C13 H13 0.9800 . ?
N13 C115 1.344(3) . ?
N13 C17 1.507(3) . ?
C115 O115 1.222(3) . ?
C115 C116 1.570(3) . ?
C116 F166 1.329(3) . ?
C116 F164 1.330(3) . ?
C116 F165 1.332(3) . ?
C17 C18 1.514(3) . ?
C17 C114 1.526(3) . ?
C17 H17 0.9800 . ?
C114 H11C 0.9600 . ?
C114 H11D 0.9600 . ?
C114 H11E 0.9600 . ?
C18 C19 1.397(3) . ?
C18 C113 1.398(3) . ?
C19 C110 1.384(4) . ?
C19 H19 0.9300 . ?
C110 C111 1.388(4) . ?
C110 H110 0.9300 . ?
C111 C112 1.381(5) . ?
C111 H111 0.9300 . ?
C112 C113 1.380(5) . ?
C112 H112 0.9300 . ?
C113 H113 0.9300 . ?
C14 O14 1.422(3) . ?
C14 C15 1.542(3) . ?
C14 H14 0.9800 . ?
O14 H14A 0.8200 . ?
C15 O15 1.416(3) . ?
C15 C16 1.520(3) . ?
C15 H15 0.9800 . ?
C16 F162 1.325(3) . ?
C16 F161 1.340(3) . ?
C16 F163 1.342(3) . ?
C22' C21' 1.487(3) . ?
C22' H22A 0.9600 . ?
C22' H22B 0.9600 . ?
C22' H22C 0.9600 . ?
C21' O21 1.444(3) . ?
C21' H21A 0.9700 . ?
C21' H21B 0.9700 . ?
O21 C21 1.379(2) . ?
C21 O25 1.438(2) . ?
C21 C22 1.519(3) . ?
C21 H21 0.9800 . ?
C22 C23 1.522(3) . ?
C22 H22D 0.9700 . ?
C22 H22E 0.9700 . ?
C23 N23 1.490(2) . ?
C23 C24 1.539(3) . ?
C23 H23 0.9800 . ?
N23 C215 1.343(3) . ?
N23 C27 1.502(3) . ?
C215 O215 1.228(3) . ?
C215 C216 1.563(3) . ?
C216 F265 1.328(3) . ?
C216 F264 1.332(3) . ?
C216 F266 1.342(3) . ?
C27 C28 1.518(3) . ?
C27 C214 1.520(3) . ?
C27 H27 0.9800 . ?
C214 H21C 0.9600 . ?
C214 H21D 0.9600 . ?
C214 H21E 0.9600 . ?
C28 C213 1.398(3) . ?
C28 C29 1.399(3) . ?
C29 C210 1.380(3) . ?
C29 H29 0.9300 . ?
C210 C211 1.375(4) . ?
C210 H210 0.9300 . ?
C211 C212 1.375(5) . ?
C211 H211 0.9300 . ?
C212 C213 1.388(4) . ?
C212 H212 0.9300 . ?
C213 H213 0.9300 . ?
C24 O24 1.413(2) . ?
C24 C25 1.549(3) . ?
C24 H24 0.9800 . ?
O24 H24A 0.8200 . ?
C25 O25 1.408(3) . ?
C25 C26 1.531(3) . ?
C25 H25 0.9800 . ?
C26 F262 1.327(3) . ?
C26 F263 1.330(3) . ?
C26 F261 1.343(3) . ?
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
O14 H14A O215 0.82 2.02 2.791(2) 157.0 1_566
O14 H14A F264 0.82 2.54 3.144(2) 131.0 1_566
O24 H24A O115 0.82 1.96 2.764(2) 166.5 1_544
O24 H24A F164 0.82 2.58 3.123(3) 125.3 1_544
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
C12' C11' O11 C11 164.6(2) . . . . ?
C11' O11 C11 O15 68.0(2) . . . . ?
C11' O11 C11 C12 -172.9(2) . . . . ?
O11 C11 C12 C13 -178.87(17) . . . . ?
O15 C11 C12 C13 -60.3(2) . . . . ?
C11 C12 C13 N13 -179.56(16) . . . . ?
C11 C12 C13 C14 52.1(2) . . . . ?
C14 C13 N13 C115 59.9(2) . . . . ?
C12 C13 N13 C115 -68.9(2) . . . . ?
C14 C13 N13 C17 -122.96(18) . . . . ?
C12 C13 N13 C17 108.3(2) . . . . ?
C13 N13 C115 O115 2.2(3) . . . . ?
C17 N13 C115 O115 -174.7(2) . . . . ?
C13 N13 C115 C116 -178.61(18) . . . . ?
C17 N13 C115 C116 4.6(3) . . . . ?
O115 C115 C116 F166 110.6(3) . . . . ?
N13 C115 C116 F166 -68.7(3) . . . . ?
O115 C115 C116 F164 -7.6(3) . . . . ?
N13 C115 C116 F164 173.1(2) . . . . ?
O115 C115 C116 F165 -126.9(2) . . . . ?
N13 C115 C116 F165 53.8(3) . . . . ?
C115 N13 C17 C18 123.5(2) . . . . ?
C13 N13 C17 C18 -53.4(2) . . . . ?
C115 N13 C17 C114 -108.4(2) . . . . ?
C13 N13 C17 C114 74.7(2) . . . . ?
N13 C17 C18 C19 -73.1(2) . . . . ?
C114 C17 C18 C19 161.8(2) . . . . ?
N13 C17 C18 C113 105.6(2) . . . . ?
C114 C17 C18 C113 -19.5(3) . . . . ?
C113 C18 C19 C110 -0.5(3) . . . . ?
C17 C18 C19 C110 178.3(2) . . . . ?
C18 C19 C110 C111 0.3(4) . . . . ?
C19 C110 C111 C112 -0.9(5) . . . . ?
C110 C111 C112 C113 1.7(6) . . . . ?
C111 C112 C113 C18 -1.9(6) . . . . ?
C19 C18 C113 C112 1.3(4) . . . . ?
C17 C18 C113 C112 -177.5(3) . . . . ?
N13 C13 C14 O14 65.5(2) . . . . ?
C12 C13 C14 O14 -166.00(16) . . . . ?
N13 C13 C14 C15 -175.38(16) . . . . ?
C12 C13 C14 C15 -46.9(2) . . . . ?
O14 C14 C15 O15 170.03(16) . . . . ?
C13 C14 C15 O15 51.6(2) . . . . ?
O14 C14 C15 C16 -71.2(2) . . . . ?
C13 C14 C15 C16 170.38(18) . . . . ?
O15 C15 C16 F162 68.5(3) . . . . ?
C14 C15 C16 F162 -54.5(3) . . . . ?
O15 C15 C16 F161 -52.2(2) . . . . ?
C14 C15 C16 F161 -175.20(18) . . . . ?
O15 C15 C16 F163 -171.24(18) . . . . ?
C14 C15 C16 F163 65.7(2) . . . . ?
C16 C15 O15 C11 174.30(16) . . . . ?
C14 C15 O15 C11 -62.9(2) . . . . ?
O11 C11 O15 C15 -173.76(16) . . . . ?
C12 C11 O15 C15 66.9(2) . . . . ?
C22' C21' O21 C21 173.48(19) . . . . ?
C21' O21 C21 O25 71.7(2) . . . . ?
C21' O21 C21 C22 -169.14(18) . . . . ?
O21 C21 C22 C23 -178.25(16) . . . . ?
O25 C21 C22 C23 -60.54(19) . . . . ?
C21 C22 C23 N23 -173.23(16) . . . . ?
C21 C22 C23 C24 57.2(2) . . . . ?
C22 C23 N23 C215 -70.6(2) . . . . ?
C24 C23 N23 C215 57.9(2) . . . . ?
C22 C23 N23 C27 105.43(18) . . . . ?
C24 C23 N23 C27 -126.16(17) . . . . ?
C23 N23 C215 O215 1.2(3) . . . . ?
C27 N23 C215 O215 -174.4(2) . . . . ?
C23 N23 C215 C216 -177.56(17) . . . . ?
C27 N23 C215 C216 6.9(3) . . . . ?
O215 C215 C216 F265 -127.9(2) . . . . ?
N23 C215 C216 F265 51.0(3) . . . . ?
O215 C215 C216 F264 -7.2(3) . . . . ?
N23 C215 C216 F264 171.72(19) . . . . ?
O215 C215 C216 F266 110.6(2) . . . . ?
N23 C215 C216 F266 -70.5(2) . . . . ?
C215 N23 C27 C28 121.1(2) . . . . ?
C23 N23 C27 C28 -54.6(2) . . . . ?
C215 N23 C27 C214 -110.8(2) . . . . ?
C23 N23 C27 C214 73.5(2) . . . . ?
N23 C27 C28 C213 108.8(2) . . . . ?
C214 C27 C28 C213 -16.6(3) . . . . ?
N23 C27 C28 C29 -70.0(2) . . . . ?
C214 C27 C28 C29 164.60(19) . . . . ?
C213 C28 C29 C210 -1.1(3) . . . . ?
C27 C28 C29 C210 177.69(19) . . . . ?
C28 C29 C210 C211 0.0(4) . . . . ?
C29 C210 C211 C212 0.9(4) . . . . ?
C210 C211 C212 C213 -0.6(5) . . . . ?
C211 C212 C213 C28 -0.5(4) . . . . ?
C29 C28 C213 C212 1.3(4) . . . . ?
C27 C28 C213 C212 -177.4(2) . . . . ?
N23 C23 C24 O24 58.92(19) . . . . ?
C22 C23 C24 O24 -171.78(15) . . . . ?
N23 C23 C24 C25 177.24(15) . . . . ?
C22 C23 C24 C25 -53.46(19) . . . . ?
O24 C24 C25 O25 173.03(15) . . . . ?
C23 C24 C25 O25 55.15(19) . . . . ?
O24 C24 C25 C26 -69.0(2) . . . . ?
C23 C24 C25 C26 173.07(15) . . . . ?
O25 C25 C26 F262 70.8(2) . . . . ?
C24 C25 C26 F262 -51.5(2) . . . . ?
O25 C25 C26 F263 -167.29(17) . . . . ?
C24 C25 C26 F263 70.4(2) . . . . ?
O25 C25 C26 F261 -49.8(2) . . . . ?
C24 C25 C26 F261 -172.04(16) . . . . ?
C26 C25 O25 C21 176.01(15) . . . . ?
C24 C25 O25 C21 -61.66(19) . . . . ?
O21 C21 O25 C25 -177.40(14) . . . . ?
C22 C21 O25 C25 64.01(19) . . . . ?
