#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/57/2225717.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_2225717
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Hemamalini, Madhukar'
'Samshuddin, S.'
'Narayana, B.'
'Yathirajan, H. S.'
_publ_section_title
;
 Methyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate
;
_journal_coeditor_code           SJ2744
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o864
_journal_page_last               o865
_journal_paper_doi               10.1107/S1600536810009414
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H16 F2 O3'
_chemical_formula_moiety         'C20 H16 F2 O3'
_chemical_formula_sum            'C20 H16 F2 O3'
_chemical_formula_weight         342.33
_chemical_name_systematic
;
Methyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 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            8
_cell_length_a                   17.3774(5)
_cell_length_b                   9.0629(3)
_cell_length_c                   22.2238(7)
_cell_measurement_reflns_used    7809
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.87
_cell_measurement_theta_min      2.52
_cell_volume                     3500.02(19)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_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  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38134
_diffrn_reflns_theta_full        30.18
_diffrn_reflns_theta_max         30.17
_diffrn_reflns_theta_min         2.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9726
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         5278
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0821P)²+0.1221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1685
_reflns_number_gt                2895
_reflns_number_total             5278
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2744.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2225717
_cod_database_fobs_code          2225717
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
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
F F1A 0.13044(18) -0.1190(4) 0.76691(10) 0.1074(9) Uani d . 1 . .
F F2A -0.0040(2) -0.1767(4) 0.23590(14) 0.1323(12) Uani d . 1 . .
O O1A 0.40617(15) 0.0074(3) 0.44238(14) 0.0808(8) Uani d . 1 . .
O O2A 0.39944(18) -0.1519(3) 0.57537(17) 0.0913(9) Uani d . 1 . .
O O3A 0.41115(18) 0.0919(3) 0.57886(15) 0.0886(8) Uani d . 1 . .
C C1A 0.2085(2) -0.2420(4) 0.62524(16) 0.0726(9) Uani d . 1 . .
H H1AA 0.2232 -0.3296 0.6067 0.087 Uiso calc R 1 . .
C C2A 0.1803(3) -0.2447(5) 0.68369(19) 0.0818(11) Uani d . 1 . .
H H2AA 0.1762 -0.3329 0.7048 0.098 Uiso calc R 1 . .
C C3A 0.1588(2) -0.1153(5) 0.70904(16) 0.0751(11) Uani d . 1 . .
C C4A 0.1641(3) 0.0180(5) 0.6812(2) 0.0809(11) Uani d . 1 . .
H H4AA 0.1496 0.1046 0.7006 0.097 Uiso calc R 1 . .
C C5A 0.1921(3) 0.0189(5) 0.62256(19) 0.0763(11) Uani d . 1 . .
H H5AA 0.1957 0.1080 0.6020 0.092 Uiso calc R 1 . .
C C6A 0.21478(19) -0.1097(4) 0.59429(14) 0.0601(8) Uani d . 1 . .
C C7A 0.2441(2) -0.1129(4) 0.52993(16) 0.0615(8) Uani d . 1 . .
H H7AA 0.2645 -0.2121 0.5226 0.074 Uiso calc R 1 . .
C C8A 0.1799(2) -0.0870(4) 0.48469(15) 0.0610(8) Uani d . 1 . .
H H8AA 0.1432 -0.1673 0.4876 0.073 Uiso calc R 1 . .
H H8AB 0.1532 0.0035 0.4952 0.073 Uiso calc R 1 . .
C C9A 0.2075(2) -0.0759(4) 0.42100(15) 0.0599(8) Uani d . 1 . .
C C10A 0.2816(2) -0.0426(4) 0.40906(16) 0.0650(8) Uani d . 1 . .
H H10A 0.2969 -0.0383 0.3690 0.078 Uiso calc R 1 . .
C C11A 0.3381(2) -0.0134(4) 0.45435(17) 0.0640(9) Uani d . 1 . .
C C12A 0.3102(2) -0.0035(4) 0.51956(16) 0.0611(8) Uani d . 1 . .
H H12A 0.2909 0.0966 0.5267 0.073 Uiso calc R 1 . .
C C13A 0.1514(2) -0.1027(4) 0.37197(16) 0.0642(8) Uani d . 1 . .
C C14A 0.0756(2) -0.0588(4) 0.37815(17) 0.0698(9) Uani d . 1 . .
H H14A 0.0596 -0.0133 0.4135 0.084 Uiso calc R 1 . .
C C15A 0.0230(2) -0.0822(5) 0.3320(2) 0.0818(11) Uani d . 1 . .
H H15A -0.0279 -0.0517 0.3358 0.098 Uiso calc R 1 . .
C C16A 0.0481(3) -0.1514(6) 0.2809(2) 0.0956(14) Uani d . 1 . .
C C17A 0.1221(3) -0.1967(7) 0.2727(2) 0.1112(18) Uani d . 1 . .
H H17A 0.1371 -0.2429 0.2372 0.133 Uiso calc R 1 . .
C C18A 0.1741(3) -0.1723(6) 0.3184(2) 0.0933(14) Uani d . 1 . .
H H18A 0.2250 -0.2022 0.3137 0.112 Uiso calc R 1 . .
C C19A 0.3777(2) -0.0302(4) 0.56085(17) 0.0634(8) Uani d . 1 . .
C C20A 0.4811(4) 0.0706(6) 0.6153(3) 0.124(2) Uani d . 1 . .
H H20A 0.5034 0.1649 0.6246 0.187 Uiso calc R 1 . .
H H20B 0.5176 0.0126 0.5931 0.187 Uiso calc R 1 . .
H H20C 0.4681 0.0206 0.6520 0.187 Uiso calc R 1 . .
F F1B 0.1337(2) 0.5160(4) -0.19775(12) 0.1155(10) Uani d . 1 . .
F F2B 0.2341(2) 0.2462(4) 0.32262(14) 0.1301(11) Uani d . 1 . .
O O1B -0.15225(18) 0.6114(4) 0.12515(15) 0.0933(9) Uani d . 1 . .
O O2B -0.1376(3) 0.7363(4) -0.0131(2) 0.1300(15) Uani d . 1 A .
O O3B -0.1543(2) 0.4954(3) -0.00956(17) 0.0966(10) Uani d . 1 A .
C C1B 0.0509(2) 0.6346(5) -0.05757(19) 0.0760(10) Uani d . 1 A .
H H1BA 0.0377 0.7220 -0.0382 0.091 Uiso calc R 1 . .
C C2B 0.0835(2) 0.6400(5) -0.11435(18) 0.0781(11) Uani d . 1 . .
H H2BA 0.0924 0.7299 -0.1333 0.094 Uiso calc R 1 . .
C C3B 0.1021(3) 0.5116(5) -0.14166(17) 0.0788(11) Uani d . 1 . .
C C4B 0.0910(3) 0.3776(5) -0.1145(2) 0.0861(12) Uani d . 1 . .
H H4BA 0.1053 0.2906 -0.1337 0.103 Uiso calc R 1 . .
C C5B 0.0582(3) 0.3747(5) -0.0583(2) 0.0793(11) Uani d . 1 A .
H H5BA 0.0498 0.2842 -0.0397 0.095 Uiso calc R 1 . .
C C6B 0.0378(2) 0.5006(4) -0.02920(16) 0.0640(9) Uani d . 1 . .
C C7B 0.0036(3) 0.4823(7) 0.0331(3) 0.0566(14) Uani d P 0.818(13) A 1
H H7BA -0.0238 0.3878 0.0343 0.068 Uiso calc PR 0.818(13) A 1
C C7C 0.0136(17) 0.552(4) 0.0413(11) 0.063(7) Uani d P 0.182(13) A 2
H H7CA 0.0175 0.6596 0.0457 0.076 Uiso calc PR 0.182(13) A 2
C C8B 0.06828(19) 0.4779(4) 0.08113(15) 0.0580(8) Uani d . 1 . .
H H8BA 0.1001 0.3917 0.0741 0.070 Uiso calc R 1 A 1
H H8BB 0.1006 0.5645 0.0763 0.070 Uiso calc R 1 A 1
C C9B 0.0387(2) 0.4732(4) 0.14515(16) 0.0600(8) Uani d . 1 A .
C C10B -0.0333(2) 0.5192(4) 0.15751(17) 0.0681(9) Uani d . 1 . .
H H10B -0.0503 0.5133 0.1971 0.082 Uiso calc R 1 A .
C C11B -0.0858(2) 0.5770(5) 0.11294(19) 0.0733(10) Uani d . 1 A .
C C12B -0.0537(3) 0.6048(6) 0.0490(2) 0.0618(16) Uani d P 0.818(13) A 1
H H12B -0.0253 0.6982 0.0499 0.074 Uiso calc PR 0.818(13) A 1
C C12C -0.0661(11) 0.504(2) 0.0472(9) 0.056(6) Uani d P 0.182(13) A 2
H H12C -0.0764 0.3988 0.0421 0.067 Uiso calc PR 0.182(13) A 2
C C13B 0.0905(2) 0.4144(4) 0.19204(16) 0.0652(8) Uani d . 1 . .
C C14B 0.1692(2) 0.4082(4) 0.18360(18) 0.0715(9) Uani d . 1 A .
H H14B 0.1900 0.4412 0.1475 0.086 Uiso calc R 1 . .
C C15B 0.2173(3) 0.3544(5) 0.2275(2) 0.0835(11) Uani d . 1 . .
H H15B 0.2702 0.3523 0.2213 0.100 Uiso calc R 1 A .
C C16B 0.1867(3) 0.3042(6) 0.2801(2) 0.0904(13) Uani d . 1 A .
C C17B 0.1109(3) 0.3063(8) 0.2898(2) 0.118(2) Uani d . 1 . .
H H17B 0.0911 0.2706 0.3258 0.142 Uiso calc R 1 A .
C C18B 0.0621(3) 0.3607(7) 0.2468(2) 0.1047(17) Uani d . 1 A .
H H18B 0.0094 0.3620 0.2541 0.126 Uiso calc R 1 . .
C C19B -0.1188(3) 0.6222(6) 0.0055(2) 0.0869(13) Uani d . 1 . .
C C20B -0.2189(4) 0.5075(7) -0.0513(4) 0.135(2) Uani d . 1 . .
H H20D -0.2467 0.4160 -0.0520 0.202 Uiso calc R 1 A .
H H20E -0.1998 0.5289 -0.0909 0.202 Uiso calc R 1 . .
H H20F -0.2525 0.5854 -0.0385 0.202 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 0.0000 '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'
O O 0.0106 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'
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
C19A O3A C20A . . 115.0(3) ?
C6A C1A C2A . . 120.5(4) ?
C6A C1A H1AA . . 119.8 ?
C2A C1A H1AA . . 119.8 ?
C3A C2A C1A . . 118.2(4) ?
C3A C2A H2AA . . 120.9 ?
C1A C2A H2AA . . 120.9 ?
C2A C3A C4A . . 124.2(4) ?
C2A C3A F1A . . 117.8(4) ?
C4A C3A F1A . . 118.0(4) ?
C3A C4A C5A . . 117.0(4) ?
C3A C4A H4AA . . 121.5 ?
C5A C4A H4AA . . 121.5 ?
C6A C5A C4A . . 121.4(4) ?
C6A C5A H5AA . . 119.3 ?
C4A C5A H5AA . . 119.3 ?
C5A C6A C1A . . 118.8(3) ?
C5A C6A C7A . . 122.7(3) ?
C1A C6A C7A . . 118.5(3) ?
C6A C7A C8A . . 111.9(3) ?
C6A C7A C12A . . 112.4(3) ?
C8A C7A C12A . . 110.5(3) ?
C6A C7A H7AA . . 107.3 ?
C8A C7A H7AA . . 107.3 ?
C12A C7A H7AA . . 107.3 ?
C9A C8A C7A . . 113.6(3) ?
C9A C8A H8AA . . 108.8 ?
C7A C8A H8AA . . 108.8 ?
C9A C8A H8AB . . 108.8 ?
C7A C8A H8AB . . 108.8 ?
H8AA C8A H8AB . . 107.7 ?
C10A C9A C13A . . 121.3(3) ?
C10A C9A C8A . . 120.4(3) ?
C13A C9A C8A . . 118.3(3) ?
C9A C10A C11A . . 123.9(3) ?
C9A C10A H10A . . 118.0 ?
C11A C10A H10A . . 118.0 ?
O1A C11A C10A . . 122.5(3) ?
O1A C11A C12A . . 120.1(4) ?
C10A C11A C12A . . 117.4(3) ?
C19A C12A C11A . . 108.7(3) ?
C19A C12A C7A . . 112.7(3) ?
C11A C12A C7A . . 109.9(3) ?
C19A C12A H12A . . 108.5 ?
C11A C12A H12A . . 108.5 ?
C7A C12A H12A . . 108.5 ?
C14A C13A C18A . . 118.8(4) ?
C14A C13A C9A . . 120.4(3) ?
C18A C13A C9A . . 120.8(3) ?
C13A C14A C15A . . 120.6(4) ?
C13A C14A H14A . . 119.7 ?
C15A C14A H14A . . 119.7 ?
C16A C15A C14A . . 118.2(4) ?
C16A C15A H15A . . 120.9 ?
C14A C15A H15A . . 120.9 ?
C17A C16A F2A . . 118.5(4) ?
C17A C16A C15A . . 123.3(4) ?
F2A C16A C15A . . 118.2(4) ?
C16A C17A C18A . . 118.2(4) ?
C16A C17A H17A . . 120.9 ?
C18A C17A H17A . . 120.9 ?
C17A C18A C13A . . 120.8(4) ?
C17A C18A H18A . . 119.6 ?
C13A C18A H18A . . 119.6 ?
O2A C19A O3A . . 123.3(4) ?
O2A C19A C12A . . 123.4(3) ?
O3A C19A C12A . . 113.2(3) ?
O3A C20A H20A . . 109.5 ?
O3A C20A H20B . . 109.5 ?
H20A C20A H20B . . 109.5 ?
O3A C20A H20C . . 109.5 ?
H20A C20A H20C . . 109.5 ?
H20B C20A H20C . . 109.5 ?
C19B O3B C20B . . 116.5(4) ?
C2B C1B C6B . . 120.8(4) ?
C2B C1B H1BA . . 119.6 ?
C6B C1B H1BA . . 119.6 ?
C3B C2B C1B . . 118.5(4) ?
C3B C2B H2BA . . 120.8 ?
C1B C2B H2BA . . 120.8 ?
C2B C3B F1B . . 118.8(4) ?
C2B C3B C4B . . 122.1(4) ?
F1B C3B C4B . . 119.1(4) ?
C3B C4B C5B . . 118.4(4) ?
C3B C4B H4BA . . 120.8 ?
C5B C4B H4BA . . 120.8 ?
C6B C5B C4B . . 121.7(4) ?
C6B C5B H5BA . . 119.1 ?
C4B C5B H5BA . . 119.1 ?
C5B C6B C1B . . 118.4(4) ?
C5B C6B C7B . . 116.5(4) ?
C1B C6B C7B . . 125.1(4) ?
C5B C6B C7C . . 137.7(12) ?
C1B C6B C7C . . 102.7(12) ?
C7B C6B C7C . . 23.8(10) ?
C6B C7B C12B . . 112.7(4) ?
C6B C7B C8B . . 110.3(4) ?
C12B C7B C8B . . 109.4(5) ?
C6B C7B H7BA . . 108.1 ?
C12B C7B H7BA . . 108.1 ?
C8B C7B H7BA . . 108.1 ?
C12C C7C C8B . . 115(2) ?
C12C C7C C6B . . 103.7(19) ?
C8B C7C C6B . . 105.8(18) ?
C12C C7C H7CA . . 110.6 ?
C8B C7C H7CA . . 110.6 ?
C6B C7C H7CA . . 110.6 ?
C7C C8B C9B . . 111.2(10) ?
C7C C8B C7B . . 26.0(12) ?
C9B C8B C7B . . 113.6(3) ?
C7C C8B H8BA . . 130.1 ?
C9B C8B H8BA . . 108.8 ?
C7B C8B H8BA . . 108.8 ?
C7C C8B H8BB . . 86.3 ?
C9B C8B H8BB . . 108.8 ?
C7B C8B H8BB . . 108.8 ?
H8BA C8B H8BB . . 107.7 ?
C10B C9B C13B . . 122.3(3) ?
C10B C9B C8B . . 119.9(3) ?
C13B C9B C8B . . 117.8(3) ?
C9B C10B C11B . . 124.0(3) ?
C9B C10B H10B . . 118.0 ?
C11B C10B H10B . . 118.0 ?
O1B C11B C10B . . 122.3(4) ?
O1B C11B C12B . . 120.0(4) ?
C10B C11B C12B . . 117.5(3) ?
O1B C11B C12C . . 119.8(8) ?
C10B C11B C12C . . 109.5(7) ?
C12B C11B C12C . . 34.0(7) ?
C19B C12B C7B . . 114.8(5) ?
C19B C12B C11B . . 109.7(4) ?
C7B C12B C11B . . 109.1(4) ?
C19B C12B H12B . . 107.7 ?
C7B C12B H12B . . 107.7 ?
C11B C12B H12B . . 107.7 ?
C7C C12C C11B . . 99.1(17) ?
C7C C12C C19B . . 106.2(19) ?
C11B C12C C19B . . 97.0(11) ?
C7C C12C H12C . . 117.1 ?
C11B C12C H12C . . 117.1 ?
C19B C12C H12C . . 117.1 ?
C14B C13B C18B . . 116.9(4) ?
C14B C13B C9B . . 121.5(3) ?
C18B C13B C9B . . 121.6(4) ?
C15B C14B C13B . . 121.4(4) ?
C15B C14B H14B . . 119.3 ?
C13B C14B H14B . . 119.3 ?
C16B C15B C14B . . 119.4(4) ?
C16B C15B H15B . . 120.3 ?
C14B C15B H15B . . 120.3 ?
C17B C16B F2B . . 119.5(4) ?
C17B C16B C15B . . 121.2(4) ?
F2B C16B C15B . . 119.3(4) ?
C16B C17B C18B . . 120.3(4) ?
C16B C17B H17B . . 119.9 ?
C18B C17B H17B . . 119.9 ?
C17B C18B C13B . . 120.9(4) ?
C17B C18B H18B . . 119.5 ?
C13B C18B H18B . . 119.5 ?
O2B C19B O3B . . 122.9(5) ?
O2B C19B C12B . . 122.4(5) ?
O3B C19B C12B . . 114.6(4) ?
O2B C19B C12C . . 156.0(9) ?
O3B C19B C12C . . 81.1(8) ?
C12B C19B C12C . . 33.6(7) ?
O3B C20B H20D . . 109.5 ?
O3B C20B H20E . . 109.5 ?
H20D C20B H20E . . 109.5 ?
O3B C20B H20F . . 109.5 ?
H20D C20B H20F . . 109.5 ?
H20E C20B H20F . . 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
F1A C3A . 1.378(4) ?
F2A C16A . 1.368(5) ?
O1A C11A . 1.227(4) ?
O2A C19A . 1.210(4) ?
O3A C19A . 1.312(4) ?
O3A C20A . 1.474(6) ?
C1A C6A . 1.387(5) ?
C1A C2A . 1.388(6) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.353(7) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.360(6) ?
C4A C5A . 1.392(6) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.381(6) ?
C5A H5AA . 0.9300 ?
C6A C7A . 1.519(5) ?
C7A C8A . 1.521(5) ?
C7A C12A . 1.535(5) ?
C7A H7AA . 0.9800 ?
C8A C9A . 1.498(5) ?
C8A H8AA . 0.9700 ?
C8A H8AB . 0.9700 ?
C9A C10A . 1.350(5) ?
C9A C13A . 1.482(5) ?
C10A C11A . 1.430(5) ?
C10A H10A . 0.9300 ?
C11A C12A . 1.531(5) ?
C12A C19A . 1.509(5) ?
C12A H12A . 0.9800 ?
C13A C14A . 1.383(5) ?
C13A C18A . 1.404(6) ?
C14A C15A . 1.389(6) ?
C14A H14A . 0.9300 ?
C15A C16A . 1.370(7) ?
C15A H15A . 0.9300 ?
C16A C17A . 1.362(7) ?
C17A C18A . 1.378(7) ?
C17A H17A . 0.9300 ?
C18A H18A . 0.9300 ?
C20A H20A . 0.9600 ?
C20A H20B . 0.9600 ?
C20A H20C . 0.9600 ?
F1B C3B . 1.363(5) ?
F2B C16B . 1.359(5) ?
O1B C11B . 1.227(5) ?
O2B C19B . 1.160(5) ?
O3B C19B . 1.346(6) ?
O3B C20B . 1.461(7) ?
C1B C2B . 1.384(6) ?
C1B C6B . 1.388(6) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.352(6) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.370(7) ?
C4B C5B . 1.373(6) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.359(6) ?
C5B H5BA . 0.9300 ?
C6B C7B . 1.516(6) ?
C6B C7C . 1.69(3) ?
C7B C12B . 1.532(8) ?
C7B C8B . 1.551(7) ?
C7B H7BA . 0.9800 ?
C7C C12C . 1.46(4) ?
C7C C8B . 1.46(3) ?
C7C H7CA . 0.9800 ?
C8B C9B . 1.514(5) ?
C8B H8BA . 0.9700 ?
C8B H8BB . 0.9700 ?
C9B C10B . 1.346(5) ?
C9B C13B . 1.477(5) ?
C10B C11B . 1.445(6) ?
C10B H10B . 0.9300 ?
C11B C12B . 1.548(6) ?
C11B C12C . 1.64(2) ?
C12B C19B . 1.496(7) ?
C12B H12B . 0.9800 ?
C12C C19B . 1.685(19) ?
C12C H12C . 0.9800 ?
C13B C14B . 1.380(5) ?
C13B C18B . 1.401(6) ?
C14B C15B . 1.374(6) ?
C14B H14B . 0.9300 ?
C15B C16B . 1.363(6) ?
C15B H15B . 0.9300 ?
C16B C17B . 1.335(7) ?
C17B C18B . 1.368(7) ?
C17B H17B . 0.9300 ?
C18B H18B . 0.9300 ?
C20B H20D . 0.9600 ?
C20B H20E . 0.9600 ?
C20B H20F . 0.9600 ?
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
C8A H8AB O2B 2_565 0.9700 2.3800 3.263(5) 151.00 yes
C8B H8BB O2A 4_564 0.9700 2.5700 3.404(5) 144.00 yes
C15B H15B O1B 3_565 0.9300 2.5500 3.226(6) 130.00 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
C6A C1A C2A C3A . . . . 0.5(6) ?
C1A C2A C3A C4A . . . . -0.9(7) ?
C1A C2A C3A F1A . . . . 179.6(4) ?
C2A C3A C4A C5A . . . . 1.2(7) ?
F1A C3A C4A C5A . . . . -179.3(4) ?
C3A C4A C5A C6A . . . . -1.0(7) ?
C4A C5A C6A C1A . . . . 0.6(6) ?
C4A C5A C6A C7A . . . . 178.8(4) ?
C2A C1A C6A C5A . . . . -0.3(6) ?
C2A C1A C6A C7A . . . . -178.5(4) ?
C5A C6A C7A C8A . . . . -72.1(5) ?
C1A C6A C7A C8A . . . . 106.0(4) ?
C5A C6A C7A C12A . . . . 52.9(5) ?
C1A C6A C7A C12A . . . . -128.9(4) ?
C6A C7A C8A C9A . . . . 174.9(3) ?
C12A C7A C8A C9A . . . . 48.8(4) ?
C7A C8A C9A C10A . . . . -20.7(4) ?
C7A C8A C9A C13A . . . . 159.1(3) ?
C13A C9A C10A C11A . . . . 179.0(3) ?
C8A C9A C10A C11A . . . . -1.1(5) ?
C9A C10A C11A O1A . . . . 175.3(4) ?
C9A C10A C11A C12A . . . . -6.8(5) ?
O1A C11A C12A C19A . . . . -23.2(4) ?
C10A C11A C12A C19A . . . . 158.8(3) ?
O1A C11A C12A C7A . . . . -147.0(3) ?
C10A C11A C12A C7A . . . . 35.0(4) ?
C6A C7A C12A C19A . . . . 57.7(4) ?
C8A C7A C12A C19A . . . . -176.5(3) ?
C6A C7A C12A C11A . . . . 179.2(3) ?
C8A C7A C12A C11A . . . . -55.1(4) ?
C10A C9A C13A C14A . . . . -144.8(4) ?
C8A C9A C13A C14A . . . . 35.4(5) ?
C10A C9A C13A C18A . . . . 35.0(6) ?
C8A C9A C13A C18A . . . . -144.9(4) ?
C18A C13A C14A C15A . . . . -0.5(6) ?
C9A C13A C14A C15A . . . . 179.3(4) ?
C13A C14A C15A C16A . . . . 0.9(7) ?
C14A C15A C16A C17A . . . . -0.8(8) ?
C14A C15A C16A F2A . . . . 178.9(4) ?
F2A C16A C17A C18A . . . . -179.4(6) ?
C15A C16A C17A C18A . . . . 0.4(10) ?
C16A C17A C18A C13A . . . . 0.1(9) ?
C14A C13A C18A C17A . . . . 0.0(8) ?
C9A C13A C18A C17A . . . . -179.7(5) ?
C20A O3A C19A O2A . . . . 3.9(7) ?
C20A O3A C19A C12A . . . . -175.3(5) ?
C11A C12A C19A O2A . . . . -84.5(4) ?
C7A C12A C19A O2A . . . . 37.7(5) ?
C11A C12A C19A O3A . . . . 94.8(4) ?
C7A C12A C19A O3A . . . . -143.1(3) ?
C6B C1B C2B C3B . . . . 0.1(7) ?
C1B C2B C3B F1B . . . . 179.5(4) ?
C1B C2B C3B C4B . . . . -1.2(7) ?
C2B C3B C4B C5B . . . . 1.5(7) ?
F1B C3B C4B C5B . . . . -179.2(4) ?
C3B C4B C5B C6B . . . . -0.8(7) ?
C4B C5B C6B C1B . . . . -0.1(7) ?
C4B C5B C6B C7B . . . . -178.9(5) ?
C4B C5B C6B C7C . . . . -165.1(15) ?
C2B C1B C6B C5B . . . . 0.5(6) ?
C2B C1B C6B C7B . . . . 179.1(4) ?
C2B C1B C6B C7C . . . . 170.2(10) ?
C5B C6B C7B C12B . . . . -150.1(5) ?
C1B C6B C7B C12B . . . . 31.3(7) ?
C7C C6B C7B C12B . . . . 53(2) ?
C5B C6B C7B C8B . . . . 87.4(5) ?
C1B C6B C7B C8B . . . . -91.2(5) ?
C7C C6B C7B C8B . . . . -69(3) ?
C5B C6B C7C C12C . . . . -78(2) ?
C1B C6B C7C C12C . . . . 115(2) ?
C7B C6B C7C C12C . . . . -46(2) ?
C5B C6B C7C C8B . . . . 43(3) ?
C1B C6B C7C C8B . . . . -123.0(17) ?
C7B C6B C7C C8B . . . . 75(3) ?
C12C C7C C8B C9B . . . . -48(3) ?
C6B C7C C8B C9B . . . . -161.5(11) ?
C12C C7C C8B C7B . . . . 53(3) ?
C6B C7C C8B C7B . . . . -61(2) ?
C6B C7B C8B C7C . . . . 85(3) ?
C12B C7B C8B C7C . . . . -40(3) ?
C6B C7B C8B C9B . . . . 175.0(3) ?
C12B C7B C8B C9B . . . . 50.5(5) ?
C7C C8B C9B C10B . . . . 7.0(15) ?
C7B C8B C9B C10B . . . . -21.0(5) ?
C7C C8B C9B C13B . . . . -174.2(15) ?
C7B C8B C9B C13B . . . . 157.7(4) ?
C13B C9B C10B C11B . . . . -179.9(4) ?
C8B C9B C10B C11B . . . . -1.2(5) ?
C9B C10B C11B O1B . . . . 176.5(4) ?
C9B C10B C11B C12B . . . . -7.6(6) ?
C9B C10B C11B C12C . . . . 28.6(9) ?
C6B C7B C12B C19B . . . . 56.2(7) ?
C8B C7B C12B C19B . . . . 179.2(4) ?
C6B C7B C12B C11B . . . . 179.8(4) ?
C8B C7B C12B C11B . . . . -57.2(6) ?
O1B C11B C12B C19B . . . . -20.0(6) ?
C10B C11B C12B C19B . . . . 163.9(4) ?
C12C C11B C12B C19B . . . . 79.6(13) ?
O1B C11B C12B C7B . . . . -146.6(5) ?
C10B C11B C12B C7B . . . . 37.4(6) ?
C12C C11B C12B C7B . . . . -47.0(12) ?
C8B C7C C12C C11B . . . . 71(2) ?
C6B C7C C12C C11B . . . . -173.6(13) ?
C8B C7C C12C C19B . . . . 171.4(15) ?
C6B C7C C12C C19B . . . . -74(2) ?
O1B C11B C12C C7C . . . . 152.4(16) ?
C10B C11B C12C C7C . . . . -58.7(19) ?
C12B C11B C12C C7C . . . . 51.8(17) ?
O1B C11B C12C C19B . . . . 44.7(12) ?
C10B C11B C12C C19B . . . . -166.5(6) ?
C12B C11B C12C C19B . . . . -55.9(9) ?
C10B C9B C13B C14B . . . . -160.8(4) ?
C8B C9B C13B C14B . . . . 20.5(5) ?
C10B C9B C13B C18B . . . . 20.0(6) ?
C8B C9B C13B C18B . . . . -158.7(4) ?
C18B C13B C14B C15B . . . . -1.2(7) ?
C9B C13B C14B C15B . . . . 179.5(4) ?
C13B C14B C15B C16B . . . . 0.9(7) ?
C14B C15B C16B C17B . . . . 0.0(8) ?
C14B C15B C16B F2B . . . . 177.7(4) ?
F2B C16B C17B C18B . . . . -178.3(6) ?
C15B C16B C17B C18B . . . . -0.6(10) ?
C16B C17B C18B C13B . . . . 0.3(10) ?
C14B C13B C18B C17B . . . . 0.6(8) ?
C9B C13B C18B C17B . . . . 179.9(5) ?
C20B O3B C19B O2B . . . . 0.0(8) ?
C20B O3B C19B C12B . . . . 179.3(5) ?
C20B O3B C19B C12C . . . . 179.3(8) ?
C7B C12B C19B O2B . . . . -132.9(6) ?
C11B C12B C19B O2B . . . . 103.9(6) ?
C7B C12B C19B O3B . . . . 47.9(6) ?
C11B C12B C19B O3B . . . . -75.4(5) ?
C7B C12B C19B C12C . . . . 47.8(13) ?
C11B C12B C19B C12C . . . . -75.5(13) ?
C7C C12C C19B O2B . . . . -43(3) ?
C11B C12C C19B O2B . . . . 59(2) ?
C7C C12C C19B O3B . . . . 138.5(18) ?
C11B C12C C19B O3B . . . . -119.8(9) ?
C7C C12C C19B C12B . . . . -41.6(15) ?
C11B C12C C19B C12B . . . . 60.1(10) ?
