#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:07:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180288 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/02/7150246.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_7150246
loop_
_publ_author_name
'Crowley, Patrick J.'
'Fawcett, John'
'Griffith, Gerry A.'
'Moralee, Andrew C.'
'Percy, Jonathan M.'
'Salafia, Vittoria'
_publ_section_title
;
 Highly-functionalised difluorinated cyclohexane polyols via the
 Diels-Alder reaction: regiochemical control via the phenylsulfonyl
 group.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3297
_journal_page_last               3310
_journal_paper_doi               10.1039/b507131c
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C18 H22 F2 O4'
_chemical_formula_weight         340.36
_chemical_name_systematic
;
?
;
_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                75.465(3)
_cell_angle_beta                 71.827(3)
_cell_angle_gamma                68.790(3)
_cell_formula_units_Z            4
_cell_length_a                   10.5327(18)
_cell_length_b                   11.552(2)
_cell_length_c                   16.158(3)
_cell_measurement_reflns_used    5631
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.23
_cell_volume                     1720.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12601
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         6014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0381
_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)+(0.0537P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                5077
_reflns_number_total             6014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b507131c.txt
_cod_data_source_block           46b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1720.2(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150246
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.83581(10) -0.06555(9) 0.37052(6) 0.0494(3) Uani 1 1 d . . .
F2 F 1.01644(9) -0.14009(8) 0.26849(6) 0.0453(2) Uani 1 1 d . . .
O1 O 0.62896(10) 0.13805(9) 0.16050(7) 0.0329(2) Uani 1 1 d . . .
H1 H 0.5504 0.1926 0.1731 0.049 Uiso 1 1 calc R . .
O2 O 0.89924(9) -0.02276(8) 0.13713(6) 0.0273(2) Uani 1 1 d . . .
O3 O 0.83568(10) -0.20079(9) 0.18593(6) 0.0310(2) Uani 1 1 d . . .
O4 O 0.69794(10) 0.33799(9) 0.19586(6) 0.0321(2) Uani 1 1 d . . .
C1 C 0.70601(14) 0.12331(13) 0.22227(9) 0.0262(3) Uani 1 1 d . . .
C1' C 0.60767(15) 0.14434(14) 0.31246(10) 0.0353(4) Uani 1 1 d . . .
H1'1 H 0.5359 0.2265 0.3073 0.053 Uiso 1 1 calc R . .
H1'2 H 0.6614 0.1418 0.3530 0.053 Uiso 1 1 calc R . .
H1'3 H 0.5623 0.0782 0.3352 0.053 Uiso 1 1 calc R . .
C2 C 0.80971(14) -0.01093(13) 0.22314(9) 0.0262(3) Uani 1 1 d . . .
C3 C 0.90485(15) -0.03423(14) 0.28452(10) 0.0337(3) Uani 1 1 d . . .
C4 C 0.95620(16) 0.07149(15) 0.27793(11) 0.0385(4) Uani 1 1 d . . .
H4 H 1.0281 0.0586 0.3061 0.046 Uiso 1 1 calc R . .
C5 C 0.90542(15) 0.18304(15) 0.23418(10) 0.0354(4) Uani 1 1 d . . .
H5 H 0.9430 0.2475 0.2320 0.043 Uiso 1 1 calc R . .
C6 C 0.79243(14) 0.21438(12) 0.18777(9) 0.0281(3) Uani 1 1 d . . .
H6 H 0.8374 0.2101 0.1237 0.034 Uiso 1 1 calc R . .
C7 C 0.74047(15) -0.11378(13) 0.24277(10) 0.0302(3) Uani 1 1 d . . .
H7A H 0.7296 -0.1537 0.3054 0.036 Uiso 1 1 calc R . .
H7B H 0.6471 -0.0795 0.2293 0.036 Uiso 1 1 calc R . .
C8 C 0.89967(15) -0.13098(13) 0.10868(9) 0.0308(3) Uani 1 1 d . . .
C9 C 1.04886(17) -0.20951(14) 0.07665(11) 0.0420(4) Uani 1 1 d . . .
H9A H 1.0975 -0.2339 0.1240 0.063 Uiso 1 1 calc R . .
H9B H 1.0967 -0.1607 0.0258 0.063 Uiso 1 1 calc R . .
H9C H 1.0497 -0.2852 0.0592 0.063 Uiso 1 1 calc R . .
C10 C 0.81585(18) -0.08856(15) 0.03984(10) 0.0415(4) Uani 1 1 d . . .
H10A H 0.8086 -0.1622 0.0241 0.062 Uiso 1 1 calc R . .
H10B H 0.8630 -0.0419 -0.0128 0.062 Uiso 1 1 calc R . .
H10C H 0.7215 -0.0341 0.0635 0.062 Uiso 1 1 calc R . .
C11 C 0.75119(16) 0.43447(14) 0.13871(10) 0.0354(4) Uani 1 1 d . . .
H11A H 0.8046 0.4073 0.0809 0.043 Uiso 1 1 calc R . .
H11B H 0.8155 0.4514 0.1643 0.043 Uiso 1 1 calc R . .
C12 C 0.63176(15) 0.55100(13) 0.12672(9) 0.0294(3) Uani 1 1 d . . .
C13 C 0.62815(17) 0.66390(14) 0.14295(10) 0.0371(4) Uani 1 1 d . . .
H13 H 0.6998 0.6669 0.1656 0.045 Uiso 1 1 calc R . .
C14 C 0.52195(19) 0.77226(15) 0.12668(12) 0.0465(4) Uani 1 1 d . . .
H14 H 0.5208 0.8495 0.1380 0.056 Uiso 1 1 calc R . .
C15 C 0.41798(19) 0.76909(16) 0.09423(12) 0.0514(5) Uani 1 1 d . . .
H15 H 0.3449 0.8440 0.0826 0.062 Uiso 1 1 calc R . .
C16 C 0.42004(18) 0.65646(17) 0.07852(12) 0.0497(4) Uani 1 1 d . . .
H16 H 0.3480 0.6538 0.0561 0.060 Uiso 1 1 calc R . .
C17 C 0.52537(16) 0.54831(15) 0.09505(11) 0.0390(4) Uani 1 1 d . . .
H17 H 0.5253 0.4710 0.0847 0.047 Uiso 1 1 calc R . .
F1A F 1.26059(9) 0.18051(8) 0.37951(6) 0.0434(2) Uani 1 1 d . . .
F2A F 1.22194(10) 0.35037(9) 0.42849(6) 0.0492(3) Uani 1 1 d . . .
O1A O 0.99948(10) 0.54421(9) 0.22391(6) 0.0329(2) Uani 1 1 d . . .
H1A H 0.9440 0.6177 0.2252 0.049 Uiso 1 1 calc R . .
O2A O 1.13235(9) 0.29007(9) 0.25267(6) 0.0267(2) Uani 1 1 d . . .
O3A O 1.35107(10) 0.30716(9) 0.19292(7) 0.0341(3) Uani 1 1 d . . .
O4A O 0.76607(10) 0.54494(9) 0.37522(7) 0.0347(3) Uani 1 1 d . . .
C1A C 1.01155(15) 0.48560(13) 0.31082(9) 0.0275(3) Uani 1 1 d . . .
C1" C 1.02002(17) 0.57775(14) 0.35979(10) 0.0365(4) Uani 1 1 d . . .
H1"1 H 1.1057 0.6014 0.3307 0.055 Uiso 1 1 calc R . .
H1"2 H 1.0219 0.5383 0.4208 0.055 Uiso 1 1 calc R . .
H1"3 H 0.9379 0.6530 0.3594 0.055 Uiso 1 1 calc R . .
C2A C 1.14549(14) 0.37177(13) 0.30019(9) 0.0265(3) Uani 1 1 d . . .
C3A C 1.16216(16) 0.29537(13) 0.39072(10) 0.0333(3) Uani 1 1 d . . .
C4A C 1.03174(18) 0.27892(15) 0.45286(10) 0.0393(4) Uani 1 1 d . . .
H4A H 1.0377 0.2187 0.5049 0.047 Uiso 1 1 calc R . .
C5A C 0.90724(17) 0.34477(14) 0.43870(10) 0.0383(4) Uani 1 1 d . . .
H5A H 0.8267 0.3325 0.4825 0.046 Uiso 1 1 calc R . .
C6A C 0.88551(14) 0.43785(13) 0.35748(9) 0.0294(3) Uani 1 1 d . . .
H6A H 0.8708 0.3956 0.3158 0.035 Uiso 1 1 calc R . .
C7A C 1.27707(15) 0.40598(14) 0.24399(10) 0.0331(3) Uani 1 1 d . . .
H7A1 H 1.2522 0.4882 0.2057 0.040 Uiso 1 1 calc R . .
H7A2 H 1.3337 0.4094 0.2815 0.040 Uiso 1 1 calc R . .
C8A C 1.24900(14) 0.26779(14) 0.17687(9) 0.0307(3) Uani 1 1 d . . .
C9A C 1.20325(17) 0.34425(16) 0.09504(10) 0.0424(4) Uani 1 1 d . . .
H9A1 H 1.1689 0.4337 0.1003 0.064 Uiso 1 1 calc R . .
H9A2 H 1.1279 0.3196 0.0880 0.064 Uiso 1 1 calc R . .
H9A3 H 1.2831 0.3292 0.0436 0.064 Uiso 1 1 calc R . .
C10A C 1.30810(16) 0.12894(15) 0.17347(11) 0.0409(4) Uani 1 1 d . . .
H10D H 1.3911 0.1129 0.1239 0.061 Uiso 1 1 calc R . .
H10E H 1.2370 0.0993 0.1656 0.061 Uiso 1 1 calc R . .
H10F H 1.3346 0.0842 0.2287 0.061 Uiso 1 1 calc R . .
C11A C 0.63672(15) 0.52466(15) 0.38409(11) 0.0407(4) Uani 1 1 d . . .
H11C H 0.6179 0.4626 0.4373 0.049 Uiso 1 1 calc R . .
H11D H 0.6417 0.4911 0.3321 0.049 Uiso 1 1 calc R . .
C12A C 0.52158(15) 0.64706(15) 0.39153(10) 0.0356(4) Uani 1 1 d . . .
C13A C 0.51946(17) 0.73330(16) 0.43791(11) 0.0410(4) Uani 1 1 d . . .
H13A H 0.5926 0.7151 0.4663 0.049 Uiso 1 1 calc R . .
C14A C 0.41201(18) 0.84604(16) 0.44362(11) 0.0486(4) Uani 1 1 d . . .
H14A H 0.4121 0.9051 0.4753 0.058 Uiso 1 1 calc R . .
C15A C 0.30493(18) 0.87260(17) 0.40333(12) 0.0518(5) Uani 1 1 d . . .
H15A H 0.2311 0.9500 0.4071 0.062 Uiso 1 1 calc R . .
C16A C 0.30535(18) 0.78748(18) 0.35805(12) 0.0529(5) Uani 1 1 d . . .
H16A H 0.2312 0.8054 0.3306 0.064 Uiso 1 1 calc R . .
C17A C 0.41270(17) 0.67561(17) 0.35196(11) 0.0441(4) Uani 1 1 d . . .
H17A H 0.4119 0.6172 0.3201 0.053 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C8 110.12(10) . . ?
C7 O3 C8 107.40(10) . . ?
C11 O4 C6 113.75(10) . . ?
O1 C1 C1' 110.48(11) . . ?
O1 C1 C6 108.51(11) . . ?
C1' C1 C6 112.02(11) . . ?
O1 C1 C2 105.88(10) . . ?
C1' C1 C2 112.22(11) . . ?
C6 C1 C2 107.47(11) . . ?
O2 C2 C7 103.90(11) . . ?
O2 C2 C3 106.54(11) . . ?
C7 C2 C3 112.57(12) . . ?
O2 C2 C1 108.92(11) . . ?
C7 C2 C1 114.26(11) . . ?
C3 C2 C1 110.13(11) . . ?
F2 C3 F1 103.47(11) . . ?
F2 C3 C4 109.69(12) . . ?
F1 C3 C4 109.59(12) . . ?
F2 C3 C2 109.13(12) . . ?
F1 C3 C2 109.70(12) . . ?
C4 C3 C2 114.66(12) . . ?
C5 C4 C3 121.89(14) . . ?
C4 C5 C6 123.81(14) . . ?
O4 C6 C5 111.72(11) . . ?
O4 C6 C1 107.67(11) . . ?
C5 C6 C1 112.58(12) . . ?
O3 C7 C2 103.52(11) . . ?
O3 C8 O2 105.19(11) . . ?
O3 C8 C9 108.25(12) . . ?
O2 C8 C9 109.18(12) . . ?
O3 C8 C10 111.31(12) . . ?
O2 C8 C10 109.18(11) . . ?
C9 C8 C10 113.38(13) . . ?
O4 C11 C12 109.31(11) . . ?
C13 C12 C17 118.72(14) . . ?
C13 C12 C11 121.18(14) . . ?
C17 C12 C11 120.03(13) . . ?
C14 C13 C12 120.73(15) . . ?
C15 C14 C13 120.18(16) . . ?
C14 C15 C16 119.51(16) . . ?
C17 C16 C15 120.42(17) . . ?
C16 C17 C12 120.43(15) . . ?
C2A O2A C8A 110.16(10) . . ?
C8A O3A C7A 107.09(10) . . ?
C6A O4A C11A 113.65(11) . . ?
O1A C1A C1" 110.07(11) . . ?
O1A C1A C6A 108.52(11) . . ?
C1" C1A C6A 111.60(12) . . ?
O1A C1A C2A 105.90(11) . . ?
C1" C1A C2A 111.94(12) . . ?
C6A C1A C2A 108.59(11) . . ?
O2A C2A C7A 103.69(11) . . ?
O2A C2A C3A 106.30(11) . . ?
C7A C2A C3A 113.20(12) . . ?
O2A C2A C1A 109.35(11) . . ?
C7A C2A C1A 113.64(11) . . ?
C3A C2A C1A 110.14(11) . . ?
F1A C3A F2A 103.34(11) . . ?
F1A C3A C4A 110.00(12) . . ?
F2A C3A C4A 109.17(12) . . ?
F1A C3A C2A 109.15(12) . . ?
F2A C3A C2A 109.39(12) . . ?
C4A C3A C2A 115.14(12) . . ?
C5A C4A C3A 122.15(14) . . ?
C4A C5A C6A 123.57(14) . . ?
O4A C6A C5A 112.54(11) . . ?
O4A C6A C1A 107.16(11) . . ?
C5A C6A C1A 112.55(12) . . ?
O3A C7A C2A 103.81(11) . . ?
O3A C8A O2A 104.77(10) . . ?
O3A C8A C10A 108.41(12) . . ?
O2A C8A C10A 109.21(12) . . ?
O3A C8A C9A 111.15(12) . . ?
O2A C8A C9A 109.69(12) . . ?
C10A C8A C9A 113.25(13) . . ?
O4A C11A C12A 108.70(13) . . ?
C13A C12A C17A 118.25(15) . . ?
C13A C12A C11A 121.85(14) . . ?
C17A C12A C11A 119.89(15) . . ?
C12A C13A C14A 120.77(16) . . ?
C15A C14A C13A 119.92(17) . . ?
C16A C15A C14A 119.77(17) . . ?
C15A C16A C17A 120.31(17) . . ?
C16A C17A C12A 120.99(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.3778(18) . ?
F2 C3 1.3686(16) . ?
O1 C1 1.4156(16) . ?
O2 C2 1.4227(16) . ?
O2 C8 1.4344(16) . ?
O3 C7 1.4210(16) . ?
O3 C8 1.4233(17) . ?
O4 C11 1.4220(17) . ?
O4 C6 1.4251(16) . ?
C1 C1' 1.5197(19) . ?
C1 C6 1.5257(19) . ?
C1 C2 1.5399(19) . ?
C2 C7 1.5288(19) . ?
C2 C3 1.5333(19) . ?
C3 C4 1.474(2) . ?
C4 C5 1.314(2) . ?
C5 C6 1.489(2) . ?
C8 C9 1.502(2) . ?
C8 C10 1.511(2) . ?
C11 C12 1.493(2) . ?
C12 C13 1.379(2) . ?
C12 C17 1.382(2) . ?
C13 C14 1.376(2) . ?
C14 C15 1.368(2) . ?
C15 C16 1.378(2) . ?
C16 C17 1.370(2) . ?
F1A C3A 1.3698(16) . ?
F2A C3A 1.3771(17) . ?
O1A C1A 1.4208(16) . ?
O2A C2A 1.4227(16) . ?
O2A C8A 1.4376(16) . ?
O3A C8A 1.4201(17) . ?
O3A C7A 1.4210(16) . ?
O4A C6A 1.4221(16) . ?
O4A C11A 1.4226(18) . ?
C1A C1" 1.5175(19) . ?
C1A C6A 1.527(2) . ?
C1A C2A 1.5391(19) . ?
C2A C7A 1.527(2) . ?
C2A C3A 1.533(2) . ?
C3A C4A 1.471(2) . ?
C4A C5A 1.315(2) . ?
C5A C6A 1.494(2) . ?
C8A C10A 1.505(2) . ?
C8A C9A 1.505(2) . ?
C11A C12A 1.496(2) . ?
C12A C13A 1.379(2) . ?
C12A C17A 1.382(2) . ?
C13A C14A 1.384(2) . ?
C14A C15A 1.377(2) . ?
C15A C16A 1.363(3) . ?
C16A C17A 1.377(2) . ?
