#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/76/2227608.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_2227608
loop_
_publ_author_name
'Cai, Xu'
'Zhou, Xinbo'
'Zheng, Zhibing'
'Zhong, Wu'
'Li, Song'
_publ_section_title
;
 (3S,4R,4aS,7aR,12bS)-3-Cyclopropylmethyl-4a,9-dihydroxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium
 2,2,2-trifluoroacetate methanol solvate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2868
_journal_paper_doi               10.1107/S1600536810041164
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H26 N O4 +, C2 F3 O2 - , C H4 O'
_chemical_formula_moiety         'C21 H26 N O4 +, C2 F3 O2 - , C H4 O'
_chemical_formula_sum            'C24 H30 F3 N O7'
_chemical_formula_weight         501.49
_chemical_name_systematic
;
(3S,4R,4aS,7aR,12bS)-3-Cyclopropylmethyl-
4a,9-dihydroxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-
methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoroacetate
methanol solvate
;
_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                   9.404(2)
_cell_length_b                   12.526(3)
_cell_length_c                   19.693(5)
_cell_measurement_reflns_used    8884
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.6
_cell_volume                     2319.7(9)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'XCIF in SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       'ω and φ 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  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16033
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku/MSC, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0321
_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)+(0.0510P)²+0.2916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0789
_reflns_number_gt                2261
_reflns_number_total             2336
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            hg2721.cif
_cod_data_source_block           I
_cod_original_cell_volume        2319.8(10)
_cod_database_code               2227608
_cod_database_fobs_code          2227608
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.33431(18) 0.71301(14) 0.23591(8) 0.0281(4) Uani d . 1 . .
H H1 1.3709 0.7168 0.1971 0.042 Uiso calc R 1 . .
O O2 1.14964(17) 0.71503(13) 0.35444(7) 0.0233(4) Uani d . 1 . .
O O3 1.0961(2) 0.92317(15) 0.35475(11) 0.0430(5) Uani d . 1 . .
O O4 0.69083(18) 0.71936(12) 0.41814(7) 0.0239(4) Uani d . 1 . .
H H4 0.6411 0.7735 0.4265 0.036 Uiso calc R 1 . .
N N1 0.6598(2) 0.54016(14) 0.31973(9) 0.0224(4) Uani d . 1 . .
C C1 1.1913(3) 0.70077(18) 0.22998(12) 0.0238(5) Uani d . 1 . .
C C2 1.1185(3) 0.69242(18) 0.16778(12) 0.0258(6) Uani d . 1 . .
H H2 1.1719 0.6938 0.1268 0.031 Uiso calc R 1 . .
C C3 0.9710(3) 0.68222(18) 0.16386(12) 0.0255(5) Uani d . 1 . .
H H3 0.9263 0.6788 0.1206 0.031 Uiso calc R 1 . .
C C4 0.8880(3) 0.67693(18) 0.22272(12) 0.0230(5) Uani d . 1 . .
C C5 0.9618(3) 0.68362(17) 0.28299(11) 0.0215(5) Uani d . 1 . .
C C6 1.1068(3) 0.69866(18) 0.28753(11) 0.0219(5) Uani d . 1 . .
C C7 1.0192(3) 0.74854(18) 0.38813(11) 0.0228(5) Uani d . 1 . .
H H7 1.0236 0.7337 0.4380 0.027 Uiso calc R 1 . .
C C8 0.9985(3) 0.86850(19) 0.37436(12) 0.0271(6) Uani d . 1 . .
C C9 0.8483(3) 0.90873(18) 0.38089(13) 0.0286(6) Uani d . 1 . .
H H9A 0.8448 0.9859 0.3702 0.034 Uiso calc R 1 . .
H H9B 0.8144 0.8987 0.4281 0.034 Uiso calc R 1 . .
C C10 0.7521(3) 0.84654(17) 0.33149(12) 0.0244(5) Uani d . 1 . .
H H10A 0.6544 0.8759 0.3329 0.029 Uiso calc R 1 . .
H H10B 0.7887 0.8539 0.2846 0.029 Uiso calc R 1 . .
C C11 0.7500(3) 0.72831(18) 0.35199(11) 0.0211(5) Uani d . 1 . .
C C12 0.9008(3) 0.68246(18) 0.35386(11) 0.0211(5) Uani d . 1 . .
C C13 0.8942(3) 0.56643(18) 0.38041(12) 0.0222(5) Uani d . 1 . .
H H13A 0.9918 0.5375 0.3844 0.027 Uiso calc R 1 . .
H H13B 0.8503 0.5656 0.4261 0.027 Uiso calc R 1 . .
C C14 0.8082(3) 0.49697(17) 0.33281(12) 0.0240(5) Uani d . 1 . .
H H14A 0.8004 0.4244 0.3525 0.029 Uiso calc R 1 . .
H H14B 0.8592 0.4909 0.2890 0.029 Uiso calc R 1 . .
C C15 0.7269(3) 0.6745(2) 0.22605(12) 0.0258(6) Uani d . 1 . .
H H15A 0.6921 0.6153 0.1971 0.031 Uiso calc R 1 . .
H H15B 0.6896 0.7419 0.2069 0.031 Uiso calc R 1 . .
C C16 0.6658(3) 0.65996(17) 0.29849(11) 0.0225(5) Uani d . 1 . .
H H16 0.5658 0.6871 0.2978 0.027 Uiso calc R 1 . .
C C17 0.5940(3) 0.4752(2) 0.26332(12) 0.0293(6) Uani d . 1 . .
H H17A 0.6626 0.4674 0.2262 0.044 Uiso calc R 1 . .
H H17B 0.5087 0.5115 0.2465 0.044 Uiso calc R 1 . .
H H17C 0.5681 0.4045 0.2806 0.044 Uiso calc R 1 . .
C C18 0.5687(3) 0.52023(18) 0.38352(12) 0.0238(5) Uani d . 1 . .
H H18A 0.5718 0.4431 0.3944 0.029 Uiso calc R 1 . .
H H18B 0.6118 0.5592 0.4221 0.029 Uiso calc R 1 . .
C C19 0.4160(3) 0.55373(18) 0.37701(12) 0.0239(5) Uani d . 1 . .
H H19 0.3997 0.6289 0.3618 0.029 Uiso calc R 1 . .
C C20 0.3038(3) 0.4746(2) 0.35699(13) 0.0328(6) Uani d . 1 . .
H H20A 0.2231 0.5007 0.3293 0.039 Uiso calc R 1 . .
H H20B 0.3345 0.4007 0.3468 0.039 Uiso calc R 1 . .
C C21 0.3133(3) 0.51176(19) 0.42924(12) 0.0307(6) Uani d . 1 . .
H H21A 0.3500 0.4608 0.4634 0.037 Uiso calc R 1 . .
H H21B 0.2386 0.5608 0.4460 0.037 Uiso calc R 1 . .
F F1 0.4670(15) 0.2811(8) 0.5019(7) 0.042(3) Uani d PDU 0.290(14) A 1
F F2 0.475(2) 0.1198(14) 0.5336(8) 0.066(4) Uani d PDU 0.290(14) A 1
F F3 0.3034(9) 0.1836(19) 0.4686(7) 0.089(4) Uani d PDU 0.290(14) A 1
F F1' 0.4075(11) 0.2763(4) 0.4989(4) 0.083(2) Uani d PDU 0.710(14) A 2
F F2' 0.5213(9) 0.1381(6) 0.5325(3) 0.0609(17) Uani d PDU 0.710(14) A 2
F F3' 0.3205(5) 0.1191(5) 0.4841(2) 0.0727(15) Uani d PDU 0.710(14) A 2
O O5 0.5400(2) 0.24675(13) 0.38094(8) 0.0294(4) Uani d . 1 . .
O O6 0.5533(2) 0.07136(14) 0.40010(9) 0.0396(5) Uani d . 1 . .
C C22 0.5196(3) 0.16372(19) 0.41422(11) 0.0256(5) Uani d . 1 A .
C C23 0.4420(4) 0.1785(2) 0.48217(14) 0.0434(8) Uani d D 1 . .
O O7 0.4835(2) 0.37757(13) 0.04273(8) 0.0277(4) Uani d . 1 . .
H H7A 0.4593 0.4383 0.0566 0.042 Uiso calc R 1 . .
C C24 0.6210(3) 0.3522(2) 0.06831(13) 0.0371(7) Uani d . 1 . .
H H24A 0.6853 0.4126 0.0606 0.056 Uiso calc R 1 . .
H H24B 0.6577 0.2890 0.0449 0.056 Uiso calc R 1 . .
H H24C 0.6146 0.3377 0.1171 0.056 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1 . . 109.5 ?
C6 O2 C7 . . 103.31(17) ?
C11 O4 H4 . . 109.5 ?
C17 N1 C14 . . 108.01(18) ?
C17 N1 C18 . . 106.54(18) ?
C14 N1 C18 . . 108.35(16) ?
C17 N1 C16 . . 109.65(17) ?
C14 N1 C16 . . 110.83(18) ?
C18 N1 C16 . . 113.25(17) ?
O1 C1 C6 . . 120.0(2) ?
O1 C1 C2 . . 124.4(2) ?
C6 C1 C2 . . 115.6(2) ?
C3 C2 C1 . . 122.6(2) ?
C3 C2 H2 . . 118.7 ?
C1 C2 H2 . . 118.7 ?
C2 C3 C4 . . 120.9(2) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C5 C4 C3 . . 115.4(2) ?
C5 C4 C15 . . 117.9(2) ?
C3 C4 C15 . . 126.5(2) ?
C4 C5 C6 . . 124.2(2) ?
C4 C5 C12 . . 127.2(2) ?
C6 C5 C12 . . 108.5(2) ?
C5 C6 C1 . . 121.1(2) ?
C5 C6 O2 . . 111.5(2) ?
C1 C6 O2 . . 127.3(2) ?
O2 C7 C8 . . 107.92(18) ?
O2 C7 C12 . . 104.70(17) ?
C8 C7 C12 . . 110.80(19) ?
O2 C7 H7 . . 111.1 ?
C8 C7 H7 . . 111.1 ?
C12 C7 H7 . . 111.1 ?
O3 C8 C9 . . 123.4(2) ?
O3 C8 C7 . . 120.9(2) ?
C9 C8 C7 . . 115.5(2) ?
C8 C9 C10 . . 109.13(19) ?
C8 C9 H9A . . 109.9 ?
C10 C9 H9A . . 109.9 ?
C8 C9 H9B . . 109.9 ?
C10 C9 H9B . . 109.9 ?
H9A C9 H9B . . 108.3 ?
C11 C10 C9 . . 109.23(19) ?
C11 C10 H10A . . 109.8 ?
C9 C10 H10A . . 109.8 ?
C11 C10 H10B . . 109.8 ?
C9 C10 H10B . . 109.8 ?
H10A C10 H10B . . 108.3 ?
O4 C11 C12 . . 108.15(18) ?
O4 C11 C10 . . 108.80(18) ?
C12 C11 C10 . . 110.9(2) ?
O4 C11 C16 . . 111.95(18) ?
C12 C11 C16 . . 106.19(18) ?
C10 C11 C16 . . 110.83(18) ?
C5 C12 C11 . . 109.05(19) ?
C5 C12 C7 . . 97.19(19) ?
C11 C12 C7 . . 118.55(19) ?
C5 C12 C13 . . 109.71(18) ?
C11 C12 C13 . . 108.87(19) ?
C7 C12 C13 . . 112.68(19) ?
C14 C13 C12 . . 110.65(19) ?
C14 C13 H13A . . 109.5 ?
C12 C13 H13A . . 109.5 ?
C14 C13 H13B . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 108.1 ?
C13 C14 N1 . . 113.03(18) ?
C13 C14 H14A . . 109.0 ?
N1 C14 H14A . . 109.0 ?
C13 C14 H14B . . 109.0 ?
N1 C14 H14B . . 109.0 ?
H14A C14 H14B . . 107.8 ?
C4 C15 C16 . . 114.4(2) ?
C4 C15 H15A . . 108.7 ?
C16 C15 H15A . . 108.7 ?
C4 C15 H15B . . 108.7 ?
C16 C15 H15B . . 108.7 ?
H15A C15 H15B . . 107.6 ?
C15 C16 N1 . . 111.92(18) ?
C15 C16 C11 . . 111.50(19) ?
N1 C16 C11 . . 111.26(17) ?
C15 C16 H16 . . 107.3 ?
N1 C16 H16 . . 107.3 ?
C11 C16 H16 . . 107.3 ?
N1 C17 H17A . . 109.5 ?
N1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C19 C18 N1 . . 114.64(19) ?
C19 C18 H18A . . 108.6 ?
N1 C18 H18A . . 108.6 ?
C19 C18 H18B . . 108.6 ?
N1 C18 H18B . . 108.6 ?
H18A C18 H18B . . 107.6 ?
C20 C19 C18 . . 120.7(2) ?
C20 C19 C21 . . 59.85(16) ?
C18 C19 C21 . . 117.2(2) ?
C20 C19 H19 . . 115.8 ?
C18 C19 H19 . . 115.8 ?
C21 C19 H19 . . 115.8 ?
C21 C20 C19 . . 60.24(16) ?
C21 C20 H20A . . 117.7 ?
C19 C20 H20A . . 117.7 ?
C21 C20 H20B . . 117.7 ?
C19 C20 H20B . . 117.7 ?
H20A C20 H20B . . 114.9 ?
C20 C21 C19 . . 59.91(17) ?
C20 C21 H21A . . 117.8 ?
C19 C21 H21A . . 117.8 ?
C20 C21 H21B . . 117.8 ?
C19 C21 H21B . . 117.8 ?
H21A C21 H21B . . 114.9 ?
O6 C22 O5 . . 128.8(2) ?
O6 C22 C23 . . 115.6(2) ?
O5 C22 C23 . . 115.5(2) ?
F2 C23 F1' . . 113.3(10) ?
F2 C23 F3 . . 114.8(10) ?
F1' C23 F3 . . 76.3(7) ?
F2 C23 F2' . . 21.5(8) ?
F1' C23 F2' . . 107.8(5) ?
F3 C23 F2' . . 135.3(8) ?
F2 C23 F1 . . 105.8(11) ?
F1' C23 F1 . . 24.3(6) ?
F3 C23 F1 . . 100.4(9) ?
F2' C23 F1 . . 92.8(7) ?
F2 C23 F3' . . 82.5(8) ?
F1' C23 F3' . . 107.2(4) ?
F3 C23 F3' . . 38.0(8) ?
F2' C23 F3' . . 103.9(4) ?
F1 C23 F3' . . 130.6(6) ?
F2 C23 C22 . . 120.1(9) ?
F1' C23 C22 . . 116.7(4) ?
F3 C23 C22 . . 107.3(5) ?
F2' C23 C22 . . 109.5(4) ?
F1 C23 C22 . . 106.3(7) ?
F3' C23 C22 . . 110.9(3) ?
C24 O7 H7A . . 109.5 ?
O7 C24 H24A . . 109.5 ?
O7 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
O7 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.359(3) ?
O1 H1 . 0.8400 ?
O2 C6 . 1.393(3) ?
O2 C7 . 1.456(3) ?
O3 C8 . 1.209(3) ?
O4 C11 . 1.421(3) ?
O4 H4 . 0.8400 ?
N1 C17 . 1.510(3) ?
N1 C14 . 1.519(3) ?
N1 C18 . 1.541(3) ?
N1 C16 . 1.559(3) ?
C1 C6 . 1.384(3) ?
C1 C2 . 1.407(3) ?
C2 C3 . 1.395(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.399(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.378(3) ?
C4 C15 . 1.517(4) ?
C5 C6 . 1.380(4) ?
C5 C12 . 1.509(3) ?
C7 C8 . 1.539(3) ?
C7 C12 . 1.543(3) ?
C7 H7 . 1.0000 ?
C8 C9 . 1.505(4) ?
C9 C10 . 1.540(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.535(3) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.530(3) ?
C11 C16 . 1.572(3) ?
C12 C13 . 1.546(3) ?
C13 C14 . 1.513(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.549(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16 . 1.0000 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 C19 . 1.501(3) ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C19 C20 . 1.501(3) ?
C19 C21 . 1.506(3) ?
C19 H19 . 1.0000 ?
C20 C21 . 1.500(4) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
F1 C23 . 1.363(9) ?
F2 C23 . 1.290(10) ?
F3 C23 . 1.332(8) ?
F1' C23 . 1.309(6) ?
F2' C23 . 1.340(5) ?
F3' C23 . 1.364(5) ?
O5 C22 . 1.244(3) ?
O6 C22 . 1.231(3) ?
C22 C23 . 1.536(4) ?
O7 C24 . 1.423(3) ?
O7 H7A . 0.8400 ?
C24 H24A . 0.9800 ?
C24 H24B . 0.9800 ?
C24 H24C . 0.9800 ?
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
O1 H1 O5 3_755 0.84 1.79 2.622(2) 170.2
O4 H4 O7 3_655 0.84 1.86 2.685(2) 169.4
O7 H7A O6 3_655 0.84 1.88 2.698(2) 165.9
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
O1 C1 C2 C3 . . . . -178.6(2) ?
C6 C1 C2 C3 . . . . -0.2(3) ?
C1 C2 C3 C4 . . . . -1.7(4) ?
C2 C3 C4 C5 . . . . 0.7(3) ?
C2 C3 C4 C15 . . . . 175.0(2) ?
C3 C4 C5 C6 . . . . 2.4(3) ?
C15 C4 C5 C6 . . . . -172.4(2) ?
C3 C4 C5 C12 . . . . 178.7(2) ?
C15 C4 C5 C12 . . . . 3.9(4) ?
C4 C5 C6 C1 . . . . -4.6(4) ?
C12 C5 C6 C1 . . . . 178.6(2) ?
C4 C5 C6 O2 . . . . 172.8(2) ?
C12 C5 C6 O2 . . . . -4.0(3) ?
O1 C1 C6 C5 . . . . -178.3(2) ?
C2 C1 C6 C5 . . . . 3.3(3) ?
O1 C1 C6 O2 . . . . 4.7(4) ?
C2 C1 C6 O2 . . . . -173.7(2) ?
C7 O2 C6 C5 . . . . -20.5(2) ?
C7 O2 C6 C1 . . . . 156.8(2) ?
C6 O2 C7 C8 . . . . -81.9(2) ?
C6 O2 C7 C12 . . . . 36.2(2) ?
O2 C7 C8 O3 . . . . -17.3(3) ?
C12 C7 C8 O3 . . . . -131.4(2) ?
O2 C7 C8 C9 . . . . 157.47(19) ?
C12 C7 C8 C9 . . . . 43.4(3) ?
O3 C8 C9 C10 . . . . 116.4(3) ?
C7 C8 C9 C10 . . . . -58.2(3) ?
C8 C9 C10 C11 . . . . 63.6(2) ?
C9 C10 C11 O4 . . . . 62.3(2) ?
C9 C10 C11 C12 . . . . -56.5(2) ?
C9 C10 C11 C16 . . . . -174.2(2) ?
C4 C5 C12 C11 . . . . -28.4(3) ?
C6 C5 C12 C11 . . . . 148.30(19) ?
C4 C5 C12 C7 . . . . -152.0(2) ?
C6 C5 C12 C7 . . . . 24.7(2) ?
C4 C5 C12 C13 . . . . 90.8(3) ?
C6 C5 C12 C13 . . . . -92.5(2) ?
O4 C11 C12 C5 . . . . 175.83(18) ?
C10 C11 C12 C5 . . . . -65.0(2) ?
C16 C11 C12 C5 . . . . 55.5(2) ?
O4 C11 C12 C7 . . . . -74.4(2) ?
C10 C11 C12 C7 . . . . 44.8(3) ?
C16 C11 C12 C7 . . . . 165.30(19) ?
O4 C11 C12 C13 . . . . 56.1(2) ?
C10 C11 C12 C13 . . . . 175.36(17) ?
C16 C11 C12 C13 . . . . -64.2(2) ?
O2 C7 C12 C5 . . . . -36.6(2) ?
C8 C7 C12 C5 . . . . 79.5(2) ?
O2 C7 C12 C11 . . . . -152.89(18) ?
C8 C7 C12 C11 . . . . -36.8(3) ?
O2 C7 C12 C13 . . . . 78.3(2) ?
C8 C7 C12 C13 . . . . -165.6(2) ?
C5 C12 C13 C14 . . . . -56.7(3) ?
C11 C12 C13 C14 . . . . 62.5(2) ?
C7 C12 C13 C14 . . . . -163.8(2) ?
C12 C13 C14 N1 . . . . -55.1(2) ?
C17 N1 C14 C13 . . . . 170.77(19) ?
C18 N1 C14 C13 . . . . -74.2(2) ?
C16 N1 C14 C13 . . . . 50.6(2) ?
C5 C4 C15 C16 . . . . -10.2(3) ?
C3 C4 C15 C16 . . . . 175.7(2) ?
C4 C15 C16 N1 . . . . -84.1(3) ?
C4 C15 C16 C11 . . . . 41.3(3) ?
C17 N1 C16 C15 . . . . -47.7(3) ?
C14 N1 C16 C15 . . . . 71.5(2) ?
C18 N1 C16 C15 . . . . -166.53(19) ?
C17 N1 C16 C11 . . . . -173.2(2) ?
C14 N1 C16 C11 . . . . -54.0(2) ?
C18 N1 C16 C11 . . . . 68.0(3) ?
O4 C11 C16 C15 . . . . 177.34(18) ?
C12 C11 C16 C15 . . . . -64.8(2) ?
C10 C11 C16 C15 . . . . 55.7(3) ?
O4 C11 C16 N1 . . . . -56.9(2) ?
C12 C11 C16 N1 . . . . 60.9(2) ?
C10 C11 C16 N1 . . . . -178.62(19) ?
C17 N1 C18 C19 . . . . -61.0(2) ?
C14 N1 C18 C19 . . . . -176.99(18) ?
C16 N1 C18 C19 . . . . 59.6(3) ?
N1 C18 C19 C20 . . . . 95.2(2) ?
N1 C18 C19 C21 . . . . 164.64(19) ?
C18 C19 C20 C21 . . . . 105.7(3) ?
C18 C19 C21 C20 . . . . -111.4(2) ?
O6 C22 C23 F2 . . . . 35.2(10) ?
O5 C22 C23 F2 . . . . -144.7(10) ?
O6 C22 C23 F1' . . . . 178.7(6) ?
O5 C22 C23 F1' . . . . -1.3(7) ?
O6 C22 C23 F3 . . . . -98.2(11) ?
O5 C22 C23 F3 . . . . 81.8(11) ?
O6 C22 C23 F2' . . . . 55.9(5) ?
O5 C22 C23 F2' . . . . -124.1(4) ?
O6 C22 C23 F1 . . . . 155.0(6) ?
O5 C22 C23 F1 . . . . -25.0(7) ?
O6 C22 C23 F3' . . . . -58.1(4) ?
O5 C22 C23 F3' . . . . 121.9(4) ?
