#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/11/2001180.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_2001180
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          366
_chemical_name_systematic
;(+-)(1R,2S,3R,6S,7R,8S,13S)-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           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8700(10)
_cell_length_b                   13.845(2)
_cell_length_c                   22.664(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      17.36
_cell_measurement_theta_min      11.36
_cell_volume                     1841.9(4)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'TEXSAN: PROCESS (MSC)'
_computing_molecular_graphics    'TEXSAN: ORTEPII (Johnson)'
_computing_publication_material  'TEXSAN: FINISH (MSC)'
_computing_structure_refinement  'TEXSAN: LS (MSC)'
_computing_structure_solution    'TEXSAN: MITHRIL (Gilmore)'
_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  2.40
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1776
_diffrn_reflns_theta_max         23.9293
_diffrn_reflns_theta_min         0
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.1102
_exptl_absorpt_correction_type   'not applied'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       plate
_exptl_crystal_F_000             816.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.05
_refine_diff_density_max         -0.29936
_refine_diff_density_min         0.26681
_refine_ls_abs_structure_details
'Mo anomolous component too low for absolute configuration determinations'
_refine_ls_extinction_method     'not applied'
_refine_ls_goodness_of_fit_obs   1.954
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         866
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0689
_refine_ls_shift/esd_max         0.0016
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0349
_reflns_number_observed          866
_reflns_number_total             1719
_reflns_observed_criterion       F>3\sF
_cod_data_source_file            hu1033.cif
_cod_data_source_block           U152
_cod_original_cell_volume        1841.9(7)
_cod_original_sg_symbol_H-M      'P 21 21 21             '
_cod_database_code               2001180
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
0.5-x,-y,0.5+z
0.5+x,0.5-y,-z
-x,0.5+y,0.5-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
F1 0.548(2) 0.5572(6) 0.8244(3) 0.1138
F2 0.7980(10) 0.6551(4) 0.8249(2) 0.0950
F3 0.878(2) 0.5067(6) 0.8250(3) 0.1440
O1 0.9400(10) 0.3594(4) 0.6565(3) 0.0466
O2 0.678(2) 0.2748(6) 0.7006(3) 0.0907
O11 0.5750(10) 0.6058(4) 0.6487(3) 0.0449
O12 1.029(2) 0.7960(6) 0.6035(4) 0.0749
C1 0.651(2) 0.6558(8) 0.7003(4) 0.0468
C2 0.853(2) 0.7173(7) 0.6796(4) 0.0473
C3 0.826(3) 0.8041(8) 0.6379(4) 0.0632
C4 0.643(3) 0.7844(9) 0.5933(6) 0.0720
C5 0.736(3) 0.7230(9) 0.5561(5) 0.0715
C6 0.968(3) 0.7045(8) 0.5778(5) 0.0660
C7 0.960(2) 0.6406(8) 0.6352(4) 0.0449
C8 0.794(2) 0.5587(7) 0.6395(4) 0.0415
C9 0.831(2) 0.5115(7) 0.7002(4) 0.0423
C10 0.745(2) 0.5742(7) 0.7376(4) 0.0367
C13 0.967(2) 0.4233(8) 0.7083(4) 0.0396
C14 0.770(2) 0.2958(8) 0.6571(5) 0.0506
C15 0.741(2) 0.2534(8) 0.5964(4) 0.0620
C16 0.658(3) 0.3327(9) 0.5550(5) 0.0544
C17 0.797(3) 0.3670(10) 0.5123(7) 0.0623
C18 0.742(4) 0.4380(10) 0.4748(7) 0.1071
C19 0.546(4) 0.4800(10) 0.4825(7) 0.0989
C20 0.393(2) 0.4490(10) 0.5244(8) 0.0937
C21 0.451(3) 0.3730(10) 0.5605(6) 0.0630
C22 1.226(2) 0.4413(8) 0.7146(4) 0.0572
C23 0.757(3) 0.5673(9) 0.8022(5) 0.0673
H1 0.5352 0.6920 0.7194 0.0563
H2 0.9539 0.7314 0.7112 0.0567
H3 0.8100 0.8643 0.6577 0.0758
H4 0.4929 0.8104 0.5922 0.0865
H5 0.6667 0.6960 0.5220 0.0856
H6 1.0705 0.6819 0.5485 0.0791
H7 1.1079 0.6215 0.6472 0.0538
H8 0.7975 0.5150 0.6072 0.0497
H13 0.9143 0.3903 0.7424 0.0476
H15A 0.6326 0.2025 0.5976 0.0743
H15B 0.8829 0.2290 0.5828 0.0743
H17 0.9442 0.3388 0.5088 0.0748
H18 0.8418 0.4563 0.4437 0.1287
H19 0.5077 0.5347 0.4589 0.1185
H20 0.2479 0.4786 0.5282 0.1124
H21 0.3461 0.3498 0.5891 0.0756
H22A 1.3029 0.3812 0.7179 0.0686
H22B 1.2539 0.4790 0.7488 0.0686
H22C 1.2800 0.4748 0.6808 0.0686
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 1 -6
1 -3 1
1 1 6
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 . . . 123.0(10) yes
C1 C2 C7 . . . 97.3(8) yes
C3 C2 C7 . . . 100.0(8) yes
C2 C7 C6 . . . 99.2(8) yes
C2 C7 C8 . . . 102.0(8) yes
C6 C7 C8 . . . 120.0(10) 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 . . 1.530(10) yes
C1 C10 . . 1.510(10) yes
C2 C3 . . 1.540(10) yes
C2 C7 . . 1.590(10) yes
C3 C4 . . 1.50(2) yes
C4 C5 . . 1.320(10) yes
C5 C6 . . 1.47(2) yes
C6 C7 . . 1.570(10) yes
C7 C8 . . 1.500(10) yes
C8 C9 . . 1.540(10) yes
C9 C10 . . 1.310(10) yes
