#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/72/2017254.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_2017254
loop_
_publ_author_name
'Ha, Jeong-Myeong'
'Young, Victor'
_publ_section_title
;
 Enantiotropic phase transition and twinning in
 2,2,3,3,4,4-hexafluoropentane-1,5-diol
;
_journal_coeditor_code           GZ3166
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o388
_journal_page_last               o395
_journal_paper_doi               10.1107/S0108270109025141
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C5 H6 F6 O2'
_chemical_formula_moiety         'C5 H6 F6 O2'
_chemical_formula_sum            'C5 H6 F6 O2'
_chemical_formula_weight         212.10
_chemical_name_common            II
_chemical_name_systematic
;
2,2,3,3,4,4-hexafluoropentane-1,5-diol
;
_space_group_IT_number           1
_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           SHELXL97
_cell_angle_alpha                82.814(3)
_cell_angle_beta                 87.274(3)
_cell_angle_gamma                86.435(4)
_cell_formula_units_Z            2
_cell_length_a                   4.8641(12)
_cell_length_b                   5.7380(14)
_cell_length_c                   13.325(3)
_cell_measurement_reflns_used    2983
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      3.725
_cell_volume                     367.97(15)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD Platform'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5181
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.9609
_exptl_absorpt_correction_T_min  0.9218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS, Version 2008/1; Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.388
_refine_ls_abs_structure_details 'Flack (1983), with how many Friedel pairs?'
_refine_ls_abs_structure_Flack   -0.8(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         1652
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0537
_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)+(0.0784P)²+0.0456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                1289
_reflns_number_total             1652
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gz3166.cif
_cod_data_source_block           II
_cod_original_cell_volume        367.98(16)
_cod_database_code               2017254
_cod_database_fobs_code          2017254
loop_
_symmetry_equiv_pos_as_xyz
'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 0.4059(8) 0.3817(6) 0.8853(2) 0.0346(9) Uani d . 1 . .
F F2 -0.0025(8) 0.5432(6) 0.8558(3) 0.0348(9) Uani d . 1 . .
F F3 0.4761(7) 0.2581(6) 0.7018(3) 0.0320(8) Uani d . 1 . .
F F4 0.0464(7) 0.3487(6) 0.6670(2) 0.0333(9) Uani d . 1 . .
F F5 0.5090(8) 0.7370(6) 0.7351(3) 0.0328(8) Uani d . 1 . .
F F6 0.0999(7) 0.7996(6) 0.6739(2) 0.0304(8) Uani d . 1 . .
O O1 -0.0047(9) 0.1011(7) 0.9698(3) 0.0310(10) Uani d . 1 . .
H H1A 0.1369 0.0484 1.0007 0.047 Uiso calc R 1 . .
O O2 0.4994(10) 0.9049(7) 0.5273(3) 0.0347(10) Uani d . 1 . .
H H2A 0.3564 0.9660 0.4995 0.052 Uiso calc R 1 . .
F F7 0.5730(8) 0.3695(6) 0.3820(3) 0.0354(9) Uani d . 1 . .
F F8 0.9676(8) 0.5310(6) 0.3562(2) 0.0359(9) Uani d . 1 . .
F F9 0.5695(7) 0.2604(5) 0.1976(2) 0.0307(8) Uani d . 1 . .
F F10 0.9979(7) 0.3423(6) 0.1650(2) 0.0306(8) Uani d . 1 . .
F F11 0.4824(7) 0.7441(6) 0.2379(2) 0.0310(8) Uani d . 1 . .
F F12 0.8956(7) 0.7916(6) 0.1720(2) 0.0291(8) Uani d . 1 . .
O O3 0.9963(9) 0.0837(7) 0.4664(3) 0.0311(10) Uani d . 1 . .
H H3A 0.8441 0.0523 0.4959 0.047 Uiso calc R 1 . .
O O4 0.5023(9) 0.9131(7) 0.0305(3) 0.0332(10) Uani d . 1 . .
H H4A 0.6488 0.9785 0.0115 0.050 Uiso calc R 1 . .
C C1 0.0582(14) 0.1288(10) 0.8631(4) 0.0270(13) Uani d . 1 . .
H H1C -0.1113 0.1178 0.8260 0.032 Uiso calc R 1 . .
H H1B 0.1930 0.0020 0.8459 0.032 Uiso calc R 1 . .
C C2 0.1767(12) 0.3656(10) 0.8321(4) 0.0235(12) Uani d . 1 . .
C C3 0.2586(12) 0.4082(10) 0.7184(4) 0.0208(10) Uani d . 1 . .
C C4 0.3345(12) 0.6552(9) 0.6731(4) 0.0207(11) Uani d . 1 . .
C C5 0.4570(14) 0.6668(10) 0.5657(4) 0.0289(13) Uani d . 1 . .
H H5A 0.6347 0.5729 0.5652 0.035 Uiso calc R 1 . .
H H5B 0.3303 0.6001 0.5223 0.035 Uiso calc R 1 . .
C C6 0.9648(13) 0.1191(10) 0.3606(4) 0.0258(12) Uani d . 1 . .
H H6A 0.8558 -0.0062 0.3404 0.031 Uiso calc R 1 . .
H H6B 1.1480 0.1111 0.3251 0.031 Uiso calc R 1 . .
C C7 0.8208(13) 0.3554(9) 0.3311(4) 0.0243(12) Uani d . 1 . .
C C8 0.7657(12) 0.4043(10) 0.2170(4) 0.0223(11) Uani d . 1 . .
C C9 0.6752(12) 0.6559(10) 0.1733(4) 0.0237(12) Uani d . 1 . .
C C10 0.5647(13) 0.6744(10) 0.0673(4) 0.0262(12) Uani d . 1 . .
H H10B 0.7043 0.6053 0.0213 0.031 Uiso calc R 1 . .
H H10A 0.3965 0.5850 0.0691 0.031 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
C1 O1 H1A . . 109.5 ?
C5 O2 H2A . . 109.5 ?
C6 O3 H3A . . 109.5 ?
C10 O4 H4A . . 109.5 ?
O1 C1 C2 . . 109.3(4) ?
O1 C1 H1C . . 109.8 ?
C2 C1 H1C . . 109.8 ?
O1 C1 H1B . . 109.8 ?
C2 C1 H1B . . 109.8 ?
H1C C1 H1B . . 108.3 ?
F2 C2 F1 . . 105.9(4) ?
F2 C2 C1 . . 111.2(5) ?
F1 C2 C1 . . 109.5(4) ?
F2 C2 C3 . . 108.9(4) ?
F1 C2 C3 . . 108.0(4) ?
C1 C2 C3 . . 113.0(4) ?
F3 C3 F4 . . 107.7(4) ?
F3 C3 C4 . . 107.8(4) ?
F4 C3 C4 . . 107.7(4) ?
F3 C3 C2 . . 107.2(4) ?
F4 C3 C2 . . 107.5(5) ?
C4 C3 C2 . . 118.5(4) ?
F5 C4 F6 . . 106.3(4) ?
F5 C4 C5 . . 110.9(5) ?
F6 C4 C5 . . 109.2(4) ?
F5 C4 C3 . . 108.8(4) ?
F6 C4 C3 . . 107.7(4) ?
C5 C4 C3 . . 113.6(4) ?
O2 C5 C4 . . 109.5(4) ?
O2 C5 H5A . . 109.8 ?
C4 C5 H5A . . 109.8 ?
O2 C5 H5B . . 109.8 ?
C4 C5 H5B . . 109.8 ?
H5A C5 H5B . . 108.2 ?
O3 C6 C7 . . 109.7(4) ?
O3 C6 H6A . . 109.7 ?
C7 C6 H6A . . 109.7 ?
O3 C6 H6B . . 109.7 ?
C7 C6 H6B . . 109.7 ?
H6A C6 H6B . . 108.2 ?
F8 C7 F7 . . 106.8(4) ?
F8 C7 C6 . . 111.1(5) ?
F7 C7 C6 . . 109.9(4) ?
F8 C7 C8 . . 108.3(4) ?
F7 C7 C8 . . 107.2(5) ?
C6 C7 C8 . . 113.2(4) ?
F10 C8 F9 . . 107.3(4) ?
F10 C8 C9 . . 107.2(4) ?
F9 C8 C9 . . 107.9(5) ?
F10 C8 C7 . . 108.1(5) ?
F9 C8 C7 . . 107.7(4) ?
C9 C8 C7 . . 118.2(4) ?
F11 C9 F12 . . 106.0(4) ?
F11 C9 C10 . . 110.3(5) ?
F12 C9 C10 . . 109.6(4) ?
F11 C9 C8 . . 108.8(4) ?
F12 C9 C8 . . 108.1(5) ?
C10 C9 C8 . . 113.8(5) ?
O4 C10 C9 . . 110.0(5) ?
O4 C10 H10B . . 109.7 ?
C9 C10 H10B . . 109.7 ?
O4 C10 H10A . . 109.7 ?
C9 C10 H10A . . 109.7 ?
H10B C10 H10A . . 108.2 ?
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 C2 . 1.364(7) ?
F2 C2 . 1.357(7) ?
F3 C3 . 1.350(6) ?
F4 C3 . 1.350(6) ?
F5 C4 . 1.355(6) ?
F6 C4 . 1.368(6) ?
O1 C1 . 1.431(6) ?
O1 H1A . 0.8400 ?
O2 C5 . 1.421(7) ?
O2 H2A . 0.8400 ?
F7 C7 . 1.358(6) ?
F8 C7 . 1.354(6) ?
F9 C8 . 1.354(6) ?
F10 C8 . 1.348(6) ?
F11 C9 . 1.360(6) ?
F12 C9 . 1.362(6) ?
O3 C6 . 1.414(6) ?
O3 H3A . 0.8400 ?
O4 C10 . 1.415(7) ?
O4 H4A . 0.8400 ?
C1 C2 . 1.511(8) ?
C1 H1C . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.541(6) ?
C3 C4 . 1.529(7) ?
C4 C5 . 1.519(7) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.503(8) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.545(7) ?
C8 C9 . 1.533(7) ?
C9 C10 . 1.525(7) ?
C10 H10B . 0.9900 ?
C10 H10A . 0.9900 ?
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
O1 H1A O4 1_546 0.84 1.93 2.746(6) 162.5 n
O2 H2A O3 1_465 0.84 1.89 2.714(6) 166.9 n
O3 H3A O2 1_545 0.84 1.93 2.733(6) 159.5 n
O4 H4A O1 1_664 0.84 1.90 2.736(6) 175.2 n
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 F2 . . . . -58.7(6) ?
O1 C1 C2 F1 . . . . 57.9(6) ?
O1 C1 C2 C3 . . . . 178.4(5) ?
F2 C2 C3 F3 . . . . 167.7(4) ?
F1 C2 C3 F3 . . . . 53.1(5) ?
C1 C2 C3 F3 . . . . -68.2(6) ?
F2 C2 C3 F4 . . . . -76.7(5) ?
F1 C2 C3 F4 . . . . 168.7(5) ?
C1 C2 C3 F4 . . . . 47.4(6) ?
F2 C2 C3 C4 . . . . 45.5(7) ?
F1 C2 C3 C4 . . . . -69.1(6) ?
C1 C2 C3 C4 . . . . 169.7(5) ?
F3 C3 C4 F5 . . . . -75.7(5) ?
F4 C3 C4 F5 . . . . 168.3(4) ?
C2 C3 C4 F5 . . . . 46.2(6) ?
F3 C3 C4 F6 . . . . 169.5(4) ?
F4 C3 C4 F6 . . . . 53.5(5) ?
C2 C3 C4 F6 . . . . -68.6(6) ?
F3 C3 C4 C5 . . . . 48.4(6) ?
F4 C3 C4 C5 . . . . -67.5(6) ?
C2 C3 C4 C5 . . . . 170.3(5) ?
F5 C4 C5 O2 . . . . -61.8(6) ?
F6 C4 C5 O2 . . . . 54.9(6) ?
C3 C4 C5 O2 . . . . 175.2(5) ?
O3 C6 C7 F8 . . . . 60.5(6) ?
O3 C6 C7 F7 . . . . -57.5(6) ?
O3 C6 C7 C8 . . . . -177.4(5) ?
F8 C7 C8 F10 . . . . 78.0(5) ?
F7 C7 C8 F10 . . . . -167.1(4) ?
C6 C7 C8 F10 . . . . -45.7(6) ?
F8 C7 C8 F9 . . . . -166.4(4) ?
F7 C7 C8 F9 . . . . -51.5(5) ?
C6 C7 C8 F9 . . . . 69.8(6) ?
F8 C7 C8 C9 . . . . -43.9(7) ?
F7 C7 C8 C9 . . . . 71.0(6) ?
C6 C7 C8 C9 . . . . -167.6(5) ?
F10 C8 C9 F11 . . . . -166.0(4) ?
F9 C8 C9 F11 . . . . 78.8(5) ?
C7 C8 C9 F11 . . . . -43.6(7) ?
F10 C8 C9 F12 . . . . -51.2(5) ?
F9 C8 C9 F12 . . . . -166.5(4) ?
C7 C8 C9 F12 . . . . 71.1(6) ?
F10 C8 C9 C10 . . . . 70.7(6) ?
F9 C8 C9 C10 . . . . -44.6(6) ?
C7 C8 C9 C10 . . . . -166.9(5) ?
F11 C9 C10 O4 . . . . 61.1(6) ?
F12 C9 C10 O4 . . . . -55.3(6) ?
C8 C9 C10 O4 . . . . -176.4(5) ?
