#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:01:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178456 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/77/4027703.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4027703
loop_
_publ_author_name
'Albrecht Berkessel'
'Sonja S. Vormittag'
'Nils E. Schlörer'
'Jörg-M. Neudörfl'
_publ_section_title
;
 TEFDDOLs (α,α,α',α'-Tetrakis(perfluoroaryl/alkyl)-2,2'-dimethyl
 -1,3-dioxolane-4,5-dimethanols): Highly Fluorinated Chiral H-Bond Donors
 and Brønsted Acids with Distinct H-Bonding Patterns and Supramolecular
 Architectures
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10145
_journal_page_last               10157
_journal_paper_doi               10.1021/jo301609g
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C7 H8 Cl2 O4'
_chemical_formula_sum            'C7 H8 Cl2 O4'
_chemical_formula_weight         227.03
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 129.481(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2526(12)
_cell_length_b                   8.9791(10)
_cell_length_c                   9.7106(5)
_cell_measurement_reflns_used    2376
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.72
_cell_volume                     959.17(15)
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-Scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2376
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0303P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0664
_reflns_number_gt                1588
_reflns_number_total             1734
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301609g_si_012.cif
_cod_data_source_block           ccdc827655
_cod_original_cell_volume        959.17(14)
_cod_database_code               4027703
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.34538(5) 0.19438(7) -0.04973(8) 0.02606(16) Uani 1 1 d .
O1 O 0.28424(16) 0.4650(2) -0.0414(2) 0.0297(5) Uani 1 1 d .
O2 O 0.51881(15) 0.58528(18) 0.1335(2) 0.0197(4) Uani 1 1 d .
C1 C 0.3645(2) 0.3900(3) -0.0069(3) 0.0194(5) Uani 1 1 d .
C2 C 0.4929(2) 0.4374(3) 0.0727(3) 0.0167(5) Uani 1 1 d .
H2 H 0.546(2) 0.367(3) 0.166(3) 0.024(7) Uiso 1 1 d .
C3 C 0.5000 0.6825(4) 0.0000 0.0198(7) Uani 1 2 d S
C4 C 0.3871(2) 0.7753(3) -0.0850(3) 0.0270(6) Uani 1 1 d .
H4A H 0.3165 0.7096 -0.1403 0.029(7) Uiso 1 1 calc R
H4B H 0.3751 0.8400 -0.1762 0.039(9) Uiso 1 1 calc R
H4C H 0.3962 0.8365 0.0065 0.042(9) Uiso 1 1 calc R
Cl2 Cl 0.36715(7) -0.09692(7) 0.50845(10) 0.03291(18) Uani 1 1 d .
O3 O 0.34577(14) 0.1667(2) 0.5965(2) 0.0269(4) Uani 1 1 d .
O4 O 0.54696(15) 0.29058(18) 0.6499(2) 0.0167(3) Uani 1 1 d .
C5 C 0.4030(2) 0.0948(3) 0.5723(3) 0.0195(5) Uani 1 1 d .
C6 C 0.5138(2) 0.1430(3) 0.5919(3) 0.0167(5) Uani 1 1 d .
H6 H 0.585(2) 0.071(3) 0.683(3) 0.024(7) Uiso 1 1 d .
C7 C 0.5000 0.3894(4) 0.5000 0.0174(7) Uani 1 2 d S
C8 C 0.6042(2) 0.4816(3) 0.5431(3) 0.0256(6) Uani 1 1 d .
H8A H 0.6657 0.4158 0.5602 0.030(8) Uiso 1 1 calc R
H8B H 0.6404 0.5385 0.6526 0.050(10) Uiso 1 1 calc R
H8C H 0.5742 0.5503 0.4444 0.021(7) Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 O2 C3 110.28(18) . .
O1 C1 C2 128.3(2) . .
O1 C1 Cl1 121.28(19) . .
C2 C1 Cl1 110.41(17) . .
O2 C2 C1 112.81(19) . .
O2 C2 C2 103.34(12) . 2_655
C1 C2 C2 110.4(2) . 2_655
O2 C2 H2 112.6(16) . .
C1 C2 H2 106.0(15) . .
C2 C2 H2 111.9(15) 2_655 .
O2 C3 O2 105.4(3) . 2_655
O2 C3 C4 110.51(12) . .
O2 C3 C4 108.62(12) 2_655 .
O2 C3 C4 108.62(12) . 2_655
O2 C3 C4 110.51(12) 2_655 2_655
C4 C3 C4 113.0(3) . 2_655
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C6 O4 C7 110.64(17) . .
O3 C5 C6 127.8(2) . .
O3 C5 Cl2 121.04(19) . .
C6 C5 Cl2 111.14(17) . .
O4 C6 C5 112.15(19) . .
O4 C6 C6 103.55(12) . 2_656
C5 C6 C6 111.6(2) . 2_656
O4 C6 H6 110.4(15) . .
C5 C6 H6 107.5(14) . .
C6 C6 H6 111.7(14) 2_656 .
O4 C7 O4 104.8(3) . 2_656
O4 C7 C8 108.16(12) . .
O4 C7 C8 110.96(12) 2_656 .
O4 C7 C8 110.96(12) . 2_656
O4 C7 C8 108.16(12) 2_656 2_656
C8 C7 C8 113.5(3) . 2_656
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.786(3) .
O1 C1 1.178(3) .
O2 C2 1.403(3) .
O2 C3 1.439(3) .
C1 C2 1.525(3) .
C2 C2 1.550(5) 2_655
C2 H2 0.96(3) .
C3 O2 1.439(3) 2_655
C3 C4 1.509(3) .
C3 C4 1.509(3) 2_655
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
Cl2 C5 1.791(3) .
O3 C5 1.175(3) .
O4 C6 1.399(3) .
O4 C7 1.454(3) .
C5 C6 1.527(3) .
C6 C6 1.565(4) 2_656
C6 H6 1.04(3) .
C7 O4 1.454(3) 2_656
C7 C8 1.509(3) .
C7 C8 1.509(3) 2_656
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
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
_geom_torsion_site_symmetry_4
C3 O2 C2 C1 -96.75(19) .
C3 O2 C2 C2 22.4(3) 2_655
O1 C1 C2 O2 9.9(3) .
Cl1 C1 C2 O2 -171.13(15) .
O1 C1 C2 C2 -105.1(2) 2_655
Cl1 C1 C2 C2 73.83(16) 2_655
C2 O2 C3 O2 -9.47(12) 2_655
C2 O2 C3 C4 107.7(2) .
C2 O2 C3 C4 -127.9(2) 2_655
C7 O4 C6 C5 -98.86(19) .
C7 O4 C6 C6 21.6(3) 2_656
O3 C5 C6 O4 1.5(3) .
Cl2 C5 C6 O4 -177.19(15) .
O3 C5 C6 C6 -114.1(2) 2_656
Cl2 C5 C6 C6 67.16(16) 2_656
C6 O4 C7 O4 -9.18(11) 2_656
C6 O4 C7 C8 -127.6(2) .
C6 O4 C7 C8 107.3(2) 2_656
