#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/23/2222340.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_2222340
loop_
_publ_author_name
'Gille, Annika'
'Schürmann, Markus'
'Preut, Hans'
'Hiersemann, Martin'
_publ_section_title
;(+-)-syn-Isopropyl
 4-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)-1-hydroxy-3-methyl-2-(prop-1-ynyl)cyclopent-2-enecarboxylate
;
_journal_coeditor_code           HG2521
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1660
_journal_paper_doi               10.1107/S1600536809023162
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H18 F6 O4'
_chemical_formula_moiety         'C16 H18 F6 O4'
_chemical_formula_sum            'C16 H18 F6 O4'
_chemical_formula_weight         388.30
_chemical_name_systematic
;
(+-)-syn-Isopropyl 4-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)-1-hydroxy-
3-methyl-2-(prop-1-ynyl)cyclopent-2-enecarboxylate
;
_space_group_IT_number           2
_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                104.600(5)
_cell_angle_beta                 91.775(5)
_cell_angle_gamma                96.955(5)
_cell_formula_units_Z            2
_cell_length_a                   6.0166(4)
_cell_length_b                   11.9075(6)
_cell_length_c                   13.2798(8)
_cell_measurement_reflns_used    3408
_cell_measurement_temperature    173.0(10)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.68
_cell_volume                     912.03(10)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.0(10)
_diffrn_detector_area_resol_mean 16.0560
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur S CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7349
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_correction_T_min  0.9439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.288
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0420
_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)+(0.0599P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                2089
_reflns_number_total             3175
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2521.cif
_cod_data_source_block           I
_cod_database_code               2222340
_cod_database_fobs_code          2222340
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
F F1 0.8004(4) 0.56391(17) 0.16252(16) 0.1130(8) Uani d . 1 . .
F F2 1.0918(3) 0.49063(18) 0.10772(12) 0.1036(7) Uani d . 1 . .
F F3 0.7665(3) 0.39187(15) 0.06173(11) 0.0842(6) Uani d . 1 . .
F F4 1.0556(2) 0.43622(12) 0.40071(10) 0.0537(4) Uani d . 1 . .
F F5 0.9672(2) 0.59099(11) 0.36511(11) 0.0631(5) Uani d . 1 . .
F F6 1.2566(2) 0.51846(13) 0.30212(11) 0.0608(4) Uani d . 1 . .
O O1 0.0648(2) 0.15814(11) 0.13523(10) 0.0286(4) Uani d . 1 . .
H H1 0.0264 0.1079 0.0786 0.043 Uiso calc R 1 . .
O O2 0.6874(2) 0.38842(11) 0.26452(11) 0.0310(4) Uani d . 1 . .
O O3 0.1934(2) -0.05252(12) 0.05543(11) 0.0406(4) Uani d . 1 . .
O O4 0.4173(2) -0.03491(12) 0.19701(11) 0.0391(4) Uani d . 1 . .
C C1 0.6115(3) 0.26537(16) 0.25431(15) 0.0243(5) Uani d . 1 . .
H H1A 0.7429 0.2231 0.2609 0.029 Uiso calc R 1 . .
C C2 0.4539(3) 0.25339(16) 0.33674(15) 0.0243(5) Uani d . 1 . .
C C3 0.2714(3) 0.17686(16) 0.29615(15) 0.0231(4) Uani d . 1 . .
C C4 0.2677(3) 0.13463(16) 0.17825(14) 0.0227(4) Uani d . 1 . .
C C5 0.4762(3) 0.20733(17) 0.15116(15) 0.0293(5) Uani d . 1 . .
H H5A 0.5661 0.1562 0.1028 0.035 Uiso calc R 1 . .
H H5B 0.4311 0.2673 0.1177 0.035 Uiso calc R 1 . .
C C6 0.9030(3) 0.41341(17) 0.23280(16) 0.0299(5) Uani d . 1 . .
H H6 0.9684 0.3384 0.2098 0.036 Uiso calc R 1 . .
C C7 0.8883(5) 0.4666(2) 0.1413(2) 0.0605(8) Uani d . 1 . .
C C8 1.0461(4) 0.4918(2) 0.32484(18) 0.0397(6) Uani d . 1 . .
C C9 0.5107(3) 0.31553(18) 0.44862(15) 0.0367(6) Uani d . 1 . .
H H9A 0.3943 0.2902 0.4912 0.055 Uiso calc R 1 . .
H H9B 0.5193 0.4002 0.4574 0.055 Uiso calc R 1 . .
H H9C 0.6557 0.2970 0.4708 0.055 Uiso calc R 1 . .
C C10 0.0936(3) 0.13487(17) 0.35228(15) 0.0256(5) Uani d . 1 . .
C C11 -0.0581(3) 0.09773(18) 0.39548(16) 0.0318(5) Uani d . 1 . .
C C12 -0.2433(4) 0.0527(2) 0.44912(19) 0.0486(6) Uani d . 1 . .
H H12A -0.2256 -0.0270 0.4525 0.073 Uiso calc R 1 . .
H H12B -0.3858 0.0518 0.4109 0.073 Uiso calc R 1 . .
H H12C -0.2428 0.1032 0.5200 0.073 Uiso calc R 1 . .
C C13 0.2847(3) 0.00474(17) 0.13700(15) 0.0237(5) Uani d . 1 . .
C C14 0.4642(4) -0.15683(18) 0.16071(17) 0.0392(6) Uani d . 1 . .
H H14 0.3778 -0.1949 0.0926 0.047 Uiso calc R 1 . .
C C15 0.7079(4) -0.1520(2) 0.1452(2) 0.0602(8) Uani d . 1 . .
H H15A 0.7475 -0.1045 0.0963 0.090 Uiso calc R 1 . .
H H15B 0.7441 -0.2315 0.1168 0.090 Uiso calc R 1 . .
H H15C 0.7929 -0.1168 0.2121 0.090 Uiso calc R 1 . .
C C16 0.3840(5) -0.2186(2) 0.2411(2) 0.0710(9) Uani d . 1 . .
H H16A 0.4691 -0.1819 0.3078 0.107 Uiso calc R 1 . .
H H16B 0.4064 -0.3011 0.2184 0.107 Uiso calc R 1 . .
H H16C 0.2241 -0.2131 0.2495 0.107 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'
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
C4 O1 H1 . . 109.5 ?
C6 O2 C1 . . 115.42(14) ?
C13 O4 C14 . . 118.33(14) ?
O2 C1 C2 . . 109.65(14) ?
O2 C1 C5 . . 112.11(17) ?
C2 C1 C5 . . 105.10(14) ?
O2 C1 H1A . . 110.0 ?
C2 C1 H1A . . 110.0 ?
C5 C1 H1A . . 110.0 ?
C3 C2 C9 . . 127.42(19) ?
C3 C2 C1 . . 110.79(16) ?
C9 C2 C1 . . 121.69(16) ?
C2 C3 C10 . . 126.87(18) ?
C2 C3 C4 . . 112.41(17) ?
C10 C3 C4 . . 120.72(15) ?
O1 C4 C3 . . 108.58(14) ?
O1 C4 C13 . . 108.35(13) ?
C3 C4 C13 . . 114.56(17) ?
O1 C4 C5 . . 112.55(16) ?
C3 C4 C5 . . 103.23(14) ?
C13 C4 C5 . . 109.61(15) ?
C1 C5 C4 . . 106.17(16) ?
C1 C5 H5A . . 110.5 ?
C4 C5 H5A . . 110.5 ?
C1 C5 H5B . . 110.5 ?
C4 C5 H5B . . 110.5 ?
H5A C5 H5B . . 108.7 ?
O2 C6 C8 . . 108.60(17) ?
O2 C6 C7 . . 109.24(18) ?
C8 C6 C7 . . 113.26(19) ?
O2 C6 H6 . . 108.5 ?
C8 C6 H6 . . 108.5 ?
C7 C6 H6 . . 108.5 ?
F1 C7 F3 . . 108.0(2) ?
F1 C7 F2 . . 106.8(2) ?
F3 C7 F2 . . 106.9(2) ?
F1 C7 C6 . . 113.5(2) ?
F3 C7 C6 . . 110.3(2) ?
F2 C7 C6 . . 111.1(2) ?
F5 C8 F6 . . 107.57(18) ?
F5 C8 F4 . . 106.86(19) ?
F6 C8 F4 . . 106.70(18) ?
F5 C8 C6 . . 113.48(18) ?
F6 C8 C6 . . 112.73(19) ?
F4 C8 C6 . . 109.13(18) ?
C2 C9 H9A . . 109.5 ?
C2 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C2 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 C3 . . 177.6(2) ?
C10 C11 C12 . . 179.6(2) ?
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 ?
O3 C13 O4 . . 124.56(18) ?
O3 C13 C4 . . 122.24(17) ?
O4 C13 C4 . . 113.11(15) ?
O4 C14 C15 . . 107.02(18) ?
O4 C14 C16 . . 106.87(18) ?
C15 C14 C16 . . 115.0(2) ?
O4 C14 H14 . . 109.3 ?
C15 C14 H14 . . 109.3 ?
C16 C14 H14 . . 109.3 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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
F1 C7 . 1.302(3) ?
F2 C7 . 1.339(3) ?
F3 C7 . 1.329(3) ?
F4 C8 . 1.341(3) ?
F5 C8 . 1.319(2) ?
F6 C8 . 1.330(2) ?
O1 C4 . 1.419(2) ?
O1 H1 . 0.8400 ?
O2 C6 . 1.397(2) ?
O2 C1 . 1.452(2) ?
O3 C13 . 1.200(2) ?
O4 C13 . 1.318(2) ?
O4 C14 . 1.474(2) ?
C1 C2 . 1.492(3) ?
C1 C5 . 1.528(3) ?
C1 H1A . 1.0000 ?
C2 C3 . 1.342(2) ?
C2 C9 . 1.492(3) ?
C3 C10 . 1.434(3) ?
C3 C4 . 1.517(3) ?
C4 C13 . 1.522(3) ?
C4 C5 . 1.541(3) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C8 . 1.507(3) ?
C6 C7 . 1.510(3) ?
C6 H6 . 1.0000 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C11 . 1.192(3) ?
C11 C12 . 1.461(3) ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C14 C15 . 1.483(3) ?
C14 C16 . 1.502(4) ?
C14 H14 . 1.0000 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 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 O3 2 0.84 2.10 2.8431(17) 147.5
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
C6 O2 C1 C2 . . . . 149.56(16) ?
C6 O2 C1 C5 . . . . -94.11(18) ?
O2 C1 C2 C3 . . . . 133.92(16) ?
C5 C1 C2 C3 . . . . 13.2(2) ?
O2 C1 C2 C9 . . . . -49.5(2) ?
C5 C1 C2 C9 . . . . -170.23(17) ?
C9 C2 C3 C10 . . . . -2.3(3) ?
C1 C2 C3 C10 . . . . 173.99(18) ?
C9 C2 C3 C4 . . . . 178.06(18) ?
C1 C2 C3 C4 . . . . -5.6(2) ?
C2 C3 C4 O1 . . . . -123.92(17) ?
C10 C3 C4 O1 . . . . 56.4(2) ?
C2 C3 C4 C13 . . . . 114.83(18) ?
C10 C3 C4 C13 . . . . -64.8(2) ?
C2 C3 C4 C5 . . . . -4.3(2) ?
C10 C3 C4 C5 . . . . 176.06(16) ?
O2 C1 C5 C4 . . . . -134.32(16) ?
C2 C1 C5 C4 . . . . -15.27(19) ?
O1 C4 C5 C1 . . . . 128.89(16) ?
C3 C4 C5 C1 . . . . 12.02(18) ?
C13 C4 C5 C1 . . . . -110.46(17) ?
C1 O2 C6 C8 . . . . -119.38(18) ?
C1 O2 C6 C7 . . . . 116.65(19) ?
O2 C6 C7 F1 . . . . 60.4(2) ?
C8 C6 C7 F1 . . . . -60.8(3) ?
O2 C6 C7 F3 . . . . -60.9(3) ?
C8 C6 C7 F3 . . . . 177.9(2) ?
O2 C6 C7 F2 . . . . -179.27(18) ?
C8 C6 C7 F2 . . . . 59.6(3) ?
O2 C6 C8 F5 . . . . -58.6(2) ?
C7 C6 C8 F5 . . . . 63.0(3) ?
O2 C6 C8 F6 . . . . 178.82(17) ?
C7 C6 C8 F6 . . . . -59.6(3) ?
O2 C6 C8 F4 . . . . 60.5(2) ?
C7 C6 C8 F4 . . . . -178.0(2) ?
C14 O4 C13 O3 . . . . 2.1(3) ?
C14 O4 C13 C4 . . . . -174.52(16) ?
O1 C4 C13 O3 . . . . 25.9(2) ?
C3 C4 C13 O3 . . . . 147.25(18) ?
C5 C4 C13 O3 . . . . -97.3(2) ?
O1 C4 C13 O4 . . . . -157.37(16) ?
C3 C4 C13 O4 . . . . -36.0(2) ?
C5 C4 C13 O4 . . . . 79.5(2) ?
C13 O4 C14 C15 . . . . 115.9(2) ?
C13 O4 C14 C16 . . . . -120.4(2) ?
