#------------------------------------------------------------------------------
#$Date: 2020-04-08 08:39:14 +0300 (Wed, 08 Apr 2020) $
#$Revision: 250496 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557753.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_1557753
loop_
_publ_author_name
'Feightner, Kylie'
'Powell, Douglas R.'
'Burba, Christopher M.'
_publ_section_title
;
 2,2,3,3,4,4,5,5-Octafluorohexane-1,6-diol
;
_journal_coeditor_code           LH4054
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x200445
_journal_paper_doi               10.1107/S2414314620004459
_journal_volume                  5
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C6 H6 F8 O4'
_chemical_formula_moiety         'C6 H6 F8 O4'
_chemical_formula_sum            'C6 H6 F8 O4'
_chemical_formula_weight         294.11
_chemical_name_systematic
;
2,2,3,3,4,4,5,5-Octafluorohexane-1,6-diol
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.146(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.3009(8)
_cell_length_b                   8.6250(12)
_cell_length_c                   10.6976(14)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      3.03
_cell_volume                     489.00(12)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Photon II CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14748
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.534
_diffrn_reflns_theta_min         3.034
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.997
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.490
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.401
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.5(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0750P)²+0.0780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                2896
_reflns_number_total             2985
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh4054sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1557753
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.886
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.7033(3) 0.36867(16) 0.87486(11) 0.0193(3) Uani d 1 . .
F F2 1.1035(3) 0.40107(18) 0.84955(14) 0.0238(3) Uani d 1 . .
F F3 0.4638(2) 0.4558(2) 0.65888(13) 0.0241(3) Uani d 1 . .
F F4 0.7907(3) 0.31004(16) 0.63351(13) 0.0232(3) Uani d 1 . .
F F5 0.7219(3) 0.68928(15) 0.52189(12) 0.0214(3) Uani d 1 . .
F F6 1.0050(2) 0.51638(17) 0.48334(12) 0.0192(3) Uani d 1 . .
F F7 0.7953(2) 0.36716(19) 0.26323(13) 0.0225(3) Uani d 1 . .
F F8 0.7493(3) 0.61560(17) 0.26968(12) 0.0204(3) Uani d 1 . .
O O1 0.6422(3) 0.67095(18) 0.95429(14) 0.0166(3) Uani d 1 . .
H H1O 0.556(6) 0.614(5) 1.001(3) 0.020 Uiso d 1 . .
O O2 0.8372(3) 0.54080(17) 0.73056(13) 0.0155(3) Uani d 1 . .
O O3 0.5994(3) 0.46959(19) 0.42741(13) 0.0167(3) Uani d 1 . .
O O4 0.4017(3) 0.46960(18) 0.10482(13) 0.0155(3) Uani d 1 . .
H H4O 0.395(6) 0.376(5) 0.081(3) 0.019 Uiso d 1 . .
C C1 0.8841(4) 0.6040(2) 0.94631(18) 0.0155(3) Uani d 1 . .
H H1A 0.935916 0.560859 1.028644 0.019 Uiso calc 1 . .
H H1B 1.007975 0.684471 0.923235 0.019 Uiso calc 1 . .
C C2 0.8810(3) 0.4762(2) 0.84895(17) 0.0144(3) Uani d 1 . .
C C3 0.7124(3) 0.4577(2) 0.63955(17) 0.0137(3) Uani d 1 . .
C C4 0.7627(3) 0.5366(2) 0.51257(17) 0.0130(3) Uani d 1 . .
C C5 0.6362(3) 0.4807(2) 0.29963(17) 0.0133(3) Uani d 1 . .
C C6 0.3799(3) 0.4651(2) 0.23611(17) 0.0138(3) Uani d 1 . .
H H6A 0.301564 0.365806 0.260933 0.017 Uiso calc 1 . .
H H6B 0.269087 0.550509 0.263425 0.017 Uiso calc 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 H1O . . 108(2) ?
C3 O2 C2 . . 120.31(16) ?
C4 O3 C5 . . 121.70(15) ?
C6 O4 H4O . . 106(2) ?
O1 C1 C2 . . 109.99(15) ?
O1 C1 H1A . . 109.7 ?
C2 C1 H1A . . 109.7 ?
O1 C1 H1B . . 109.7 ?
C2 C1 H1B . . 109.7 ?
H1A C1 H1B . . 108.2 ?
F2 C2 F1 . . 106.43(17) ?
F2 C2 O2 . . 109.02(16) ?
F1 C2 O2 . . 110.76(15) ?
F2 C2 C1 . . 110.45(15) ?
F1 C2 C1 . . 110.80(16) ?
O2 C2 C1 . . 109.34(16) ?
F3 C3 F4 . . 107.59(17) ?
F3 C3 O2 . . 111.10(16) ?
F4 C3 O2 . . 112.68(16) ?
F3 C3 C4 . . 109.20(15) ?
F4 C3 C4 . . 108.44(15) ?
O2 C3 C4 . . 107.76(16) ?
F5 C4 F6 . . 107.64(16) ?
F5 C4 O3 . . 111.28(16) ?
F6 C4 O3 . . 112.68(16) ?
F5 C4 C3 . . 109.64(16) ?
F6 C4 C3 . . 109.31(15) ?
O3 C4 C3 . . 106.26(15) ?
F8 C5 F7 . . 105.85(15) ?
F8 C5 O3 . . 111.40(15) ?
F7 C5 O3 . . 109.52(16) ?
F8 C5 C6 . . 111.64(16) ?
F7 C5 C6 . . 111.42(16) ?
O3 C5 C6 . . 107.05(14) ?
O4 C6 C5 . . 110.69(14) ?
O4 C6 H6A . . 109.5 ?
C5 C6 H6A . . 109.5 ?
O4 C6 H6B . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 108.1 ?
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 . 1.354(2) ?
F2 C2 . 1.345(2) ?
F3 C3 . 1.338(2) ?
F4 C3 . 1.342(2) ?
F5 C4 . 1.338(2) ?
F6 C4 . 1.339(2) ?
F7 C5 . 1.354(2) ?
F8 C5 . 1.351(2) ?
O1 C1 . 1.410(2) ?
O1 H1O . 0.84(4) ?
O2 C3 . 1.368(2) ?
O2 C2 . 1.399(2) ?
O3 C4 . 1.372(2) ?
O3 C5 . 1.388(2) ?
O4 C6 . 1.412(2) ?
O4 H4O . 0.85(4) ?
C1 C2 . 1.517(3) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C3 C4 . 1.547(3) ?
C5 C6 . 1.513(2) ?
C6 H6A . 0.9900 ?
C6 H6B . 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 H1O O4 1_556 0.84(4) 1.87(4) 2.705(2) 172(3) yes
O4 H4O O1 2_646 0.85(4) 1.82(4) 2.661(2) 173(3) yes
C6 H6B F4 2_656 0.99 2.52 3.416(2) 150.6 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
C3 O2 C2 F2 . . . . 89.9(2) ?
C3 O2 C2 F1 . . . . -26.9(2) ?
C3 O2 C2 C1 . . . . -149.29(17) ?
O1 C1 C2 F2 . . . . -173.74(16) ?
O1 C1 C2 F1 . . . . -56.1(2) ?
O1 C1 C2 O2 . . . . 66.3(2) ?
C2 O2 C3 F3 . . . . 77.1(2) ?
C2 O2 C3 F4 . . . . -43.8(2) ?
C2 O2 C3 C4 . . . . -163.34(16) ?
C5 O3 C4 F5 . . . . 78.4(2) ?
C5 O3 C4 F6 . . . . -42.6(2) ?
C5 O3 C4 C3 . . . . -162.26(17) ?
F3 C3 C4 F5 . . . . 72.2(2) ?
F4 C3 C4 F5 . . . . -170.79(16) ?
O2 C3 C4 F5 . . . . -48.5(2) ?
F3 C3 C4 F6 . . . . -169.97(16) ?
F4 C3 C4 F6 . . . . -53.01(19) ?
O2 C3 C4 F6 . . . . 69.23(19) ?
F3 C3 C4 O3 . . . . -48.1(2) ?
F4 C3 C4 O3 . . . . 68.84(19) ?
O2 C3 C4 O3 . . . . -168.91(15) ?
C4 O3 C5 F8 . . . . -31.6(2) ?
C4 O3 C5 F7 . . . . 85.1(2) ?
C4 O3 C5 C6 . . . . -153.95(17) ?
F8 C5 C6 O4 . . . . 59.9(2) ?
F7 C5 C6 O4 . . . . -58.2(2) ?
O3 C5 C6 O4 . . . . -177.92(15) ?

_cod_database_fobs_code 1557753
