#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/11/2001179.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_2001179
loop_
_publ_author_name
'Barlow, M. G.'
'Pritchard, R. G.'
'Tajammal, S.'
'Tipping, A. E.'
_publ_section_title
;Two diastereoisomers of
 1-(10-trifluoromethyl-11,12-dioxatetracyclo[6.2.1.1^3,6^.0^2,7^]dodeca-4,9-dien-9-yl)ethyl
 phenylacetate, C₂₁H₁₉F₃O₄: members of a series of adducts generated
 by repeated Diels--Alder cycloaddition of furan to
 5,5,5-trifluoropent-3-yn-2-yl phenylacetate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2151
_journal_page_last               2153
_journal_paper_doi               10.1107/S0108270193007668
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C21 H19 F3 O4'
_chemical_formula_sum            'C21 H19 F3 O4'
_chemical_formula_weight         392.37
_chemical_melting_point          391
_chemical_name_systematic
;(+-)(1R,2S,3R,6S,7R,8S,13R)-9-[(phenylacetoxy)ethyl]-10-trifluoromethyl-
11,12-dioxatetracyclo [6.2.1.1.^3,6^0^2,7^]deca-4,9-diene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                80.480(10)
_cell_angle_beta                 87.250(10)
_cell_angle_gamma                74.500(10)
_cell_formula_units_Z            2
_cell_length_a                   5.7070(10)
_cell_length_b                   10.227(2)
_cell_length_c                   16.625(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      24.27
_cell_measurement_theta_min      10.15
_cell_volume                     922.2(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction
'TEXSAN PROCESS (Molecular Structure Corporation, 1985)'
_computing_molecular_graphics    'TEXSAN ORTEPII (Johnson, 1976)'
_computing_publication_material  'TEXSAN FINISH'
_computing_structure_refinement  'TEXSAN LS'
_computing_structure_solution    'TEXSAN MITHRIL (Gilmore, 1984)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       CAD-4
_diffrn_measurement_method       'ω/2-θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2975
_diffrn_reflns_theta_max         23.9704
_diffrn_reflns_theta_min         0
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.1101
_exptl_absorpt_correction_type   'not applied'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       plate
_exptl_crystal_F_000             408.00
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         -0.20708
_refine_diff_density_min         0.23758
_refine_ls_extinction_method     'not applied'
_refine_ls_goodness_of_fit_obs   1.734
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         1544
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0522
_refine_ls_shift/esd_max         0.0003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0298
_reflns_number_observed          1544
_reflns_number_total             2894
_reflns_observed_criterion       F>3\sF
_cod_data_source_file            hu1033.cif
_cod_data_source_block           U142
_cod_original_cell_volume        922.3(5)
_cod_original_sg_symbol_H-M      'P -1                   '
_cod_database_code               2001179
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
F1 0.7097(5) 0.1057(3) 0.0338(2) 0.0860
F2 0.9911(5) -0.0040(2) 0.1187(2) 0.0722
F3 0.6890(5) -0.0847(3) 0.1056(2) 0.0864
O1 0.2379(5) 0.4622(3) 0.1221(2) 0.0490
O2 0.5943(7) 0.5172(3) 0.1059(2) 0.0770
O11 0.4323(5) 0.1049(3) 0.2962(2) 0.0430
O12 0.8963(5) 0.2594(3) 0.3887(2) 0.0589
C1 0.6692(8) 0.0519(4) 0.2636(3) 0.0419
C2 0.8211(8) 0.1412(4) 0.2911(2) 0.0393
C3 0.9076(9) 0.1178(5) 0.3814(3) 0.0514
C4 0.7070(10) 0.0927(6) 0.4378(3) 0.0597
C5 0.5400(10) 0.2105(6) 0.4337(3) 0.0621
C6 0.6378(9) 0.3111(5) 0.3743(3) 0.0519
C7 0.6273(8) 0.2805(4) 0.2859(2) 0.0396
C8 0.4004(8) 0.2445(4) 0.2575(2) 0.0382
C9 0.4564(7) 0.2260(4) 0.1684(2) 0.0364
C10 0.6198(7) 0.1056(4) 0.1728(2) 0.0392
C13 0.3467(9) 0.3285(4) 0.0964(3) 0.0434
C14 0.3830(10) 0.5472(4) 0.1211(3) 0.0518
C15 0.2380(10) 0.6841(5) 0.1430(3) 0.0720
C16 0.1955(9) 0.6777(4) 0.2348(3) 0.0542
C17 0.3220(10) 0.7418(5) 0.2774(4) 0.0760
C18 0.2820(10) 0.7405(7) 0.3599(4) 0.0923
C19 0.1250(10) 0.6760(7) 0.4001(4) 0.0930
C20 -0.0010(10) 0.6104(7) 0.3597(5) 0.0976
C21 0.0350(10) 0.6130(6) 0.2760(4) 0.0760
C22 0.1400(10) 0.2935(6) 0.0592(4) 0.0661
C23 0.7513(9) 0.0324(5) 0.1076(3) 0.0567
H1 0.734(5) -0.049(3) 0.280(2) 0.029(10)
H2 0.964(5) 0.142(3) 0.256(2) 0.025(10)
H3 1.080(6) 0.059(3) 0.393(2) 0.040(10)
H4 0.691(6) 0.010(3) 0.464(2) 0.040(10)
H5 0.378(6) 0.229(4) 0.451(2) 0.050(10)
H6 0.572(6) 0.415(4) 0.380(2) 0.050(10)
H7 0.666(5) 0.356(3) 0.250(2) 0.021(9)
H8 0.240(6) 0.306(3) 0.268(2) 0.040(10)
H13 0.464(6) 0.342(3) 0.060(2) 0.040(10)
H15A 0.063(7) 0.695(4) 0.122(2) 0.08(2)
H15B 0.344(10) 0.753(6) 0.123(3) 0.16(2)
H17 0.455(8) 0.783(5) 0.248(3) 0.11(2)
H18 0.397(9) 0.785(5) 0.383(3) 0.13(2)
H19 0.109(8) 0.670(5) 0.455(3) 0.10(2)
H20 -0.150(10) 0.579(7) 0.376(4) 0.21(3)
H21 -0.062(8) 0.575(4) 0.245(3) 0.09(2)
H22A 0.193(6) 0.204(4) 0.042(2) 0.060(10)
H22B -0.003(8) 0.299(5) 0.099(3) 0.10(2)
H22C 0.078(8) 0.359(4) 0.015(3) 0.09(2)
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 0 6
-1 -1 -4
1 -1 -3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 C2 C3 . . . 120.9(4) yes
C1 C2 C7 . . . 100.4(3) yes
C3 C2 C7 . . . 101.6(3) yes
C2 C7 C6 . . . 100.6(3) yes
C2 C7 C8 . . . 101.8(3) yes
C6 C7 C8 . . . 119.9(4) yes
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 C2 . . 1.548(5) yes
C1 C10 . . 1.530(5) yes
C2 C3 . . 1.563(5) yes
C2 C7 . . 1.545(5) yes
C3 C4 . . 1.493(6) yes
C4 C5 . . 1.317(6) yes
C5 C6 . . 1.506(6) yes
C6 C7 . . 1.561(5) yes
C7 C8 . . 1.551(5) yes
C8 C9 . . 1.533(5) yes
C9 C10 . . 1.325(4) yes
