#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:07:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180288 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/02/7150243.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_7150243
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            'C17 H16 F2 O6 S'
_chemical_formula_weight         386.36
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 94.6090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9999(5)
_cell_length_b                   8.3226(4)
_cell_length_c                   19.8738(10)
_cell_measurement_reflns_used    7626
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.53
_cell_measurement_theta_min      2.28
_cell_volume                     1648.65(14)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11548
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
absorption correction based on 9817 reflections (SADABS);
Rint 0.026 and 0.019 before
and after correction respectively.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0309
_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)+(0.0456P)²+0.5992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0816
_reflns_number_gt                2664
_reflns_number_total             2900
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b507131c.txt
_cod_data_source_block           10b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      P2(1)/c
_cod_database_code               7150243
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S1 S 0.75893(4) 0.94441(5) 0.03106(2) 0.02760(13) Uani 1 1 d . . .
F1 F 1.15505(9) 0.70660(11) 0.06543(4) 0.0291(2) Uani 1 1 d . . .
F2 F 1.22555(9) 0.86913(11) 0.14599(5) 0.0312(2) Uani 1 1 d . . .
O1 O 0.94200(10) 0.89791(12) 0.17059(5) 0.0212(2) Uani 1 1 d . . .
O2 O 1.14147(11) 0.78074(13) 0.28047(5) 0.0269(3) Uani 1 1 d . . .
O3 O 1.26231(10) 0.58070(12) 0.23989(5) 0.0225(2) Uani 1 1 d . . .
O4 O 1.07269(9) 0.50209(12) 0.15091(5) 0.0205(2) Uani 1 1 d . . .
O5 O 0.99060(10) 0.30276(12) 0.08778(5) 0.0244(2) Uani 1 1 d . . .
O6 O 0.86439(10) 0.51803(12) 0.09136(5) 0.0237(2) Uani 1 1 d . . .
C1 C 0.92303(14) 0.72747(17) 0.17914(7) 0.0194(3) Uani 1 1 d . . .
C2 C 1.06683(14) 0.66430(17) 0.17353(7) 0.0186(3) Uani 1 1 d . . .
C3 C 1.11639(14) 0.78543(18) 0.12014(7) 0.0223(3) Uani 1 1 d . . .
C4 C 0.99637(14) 0.89601(18) 0.10569(7) 0.0221(3) Uani 1 1 d . . .
H4 H 1.0192 1.0045 0.0883 0.027 Uiso 1 1 calc R . .
C5 C 0.89033(14) 0.80492(17) 0.06085(7) 0.0219(3) Uani 1 1 d . . .
H5 H 0.9307 0.7507 0.0224 0.026 Uiso 1 1 calc R . .
C6 C 0.84413(14) 0.68163(17) 0.11204(7) 0.0205(3) Uani 1 1 d . . .
H6 H 0.7463 0.6982 0.1169 0.025 Uiso 1 1 calc R . .
C7 C 0.85392(15) 0.68613(18) 0.24122(7) 0.0232(3) Uani 1 1 d . . .
H7A H 0.9075 0.7256 0.2813 0.035 Uiso 1 1 calc R . .
H7B H 0.8441 0.5693 0.2443 0.035 Uiso 1 1 calc R . .
H7C H 0.7651 0.7365 0.2386 0.035 Uiso 1 1 calc R . .
C8 C 1.15876(14) 0.68049(17) 0.23876(7) 0.0199(3) Uani 1 1 d . . .
C9 C 1.35924(15) 0.6032(2) 0.29833(8) 0.0287(4) Uani 1 1 d . . .
H9A H 1.3172 0.5767 0.3404 0.034 Uiso 1 1 calc R . .
H9B H 1.3892 0.7166 0.3010 0.034 Uiso 1 1 calc R . .
C10 C 1.47647(18) 0.4953(3) 0.29064(10) 0.0460(5) Uani 1 1 d . . .
H10A H 1.4468 0.3830 0.2905 0.069 Uiso 1 1 calc R . .
H10B H 1.5442 0.5126 0.3284 0.069 Uiso 1 1 calc R . .
H10C H 1.5153 0.5194 0.2480 0.069 Uiso 1 1 calc R . .
C11 C 0.97571(14) 0.43551(17) 0.10856(7) 0.0194(3) Uani 1 1 d . . .
C12 C 0.64656(15) 0.80805(18) -0.01341(7) 0.0245(3) Uani 1 1 d . . .
C13 C 0.68599(16) 0.7246(2) -0.06891(8) 0.0300(4) Uani 1 1 d . . .
H13 H 0.7740 0.7382 -0.0828 0.036 Uiso 1 1 calc R . .
C14 C 0.59705(17) 0.6217(2) -0.10401(8) 0.0337(4) Uani 1 1 d . . .
H14 H 0.6250 0.5616 -0.1410 0.040 Uiso 1 1 calc R . .
C15 C 0.46749(17) 0.6061(2) -0.08536(9) 0.0316(4) Uani 1 1 d . . .
H15 H 0.4061 0.5370 -0.1102 0.038 Uiso 1 1 calc R . .
C16 C 0.42718(16) 0.6903(2) -0.03088(9) 0.0317(4) Uani 1 1 d . . .
H16 H 0.3378 0.6801 -0.0185 0.038 Uiso 1 1 calc R . .
C17 C 0.51680(16) 0.78975(19) 0.00582(8) 0.0289(4) Uani 1 1 d . . .
H17 H 0.4896 0.8455 0.0441 0.035 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'
S S 0.1246 0.1234 '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
C12 S1 C5 99.53(7) . . ?
C4 O1 C1 99.06(10) . . ?
C8 O3 C9 113.55(11) . . ?
C11 O4 C2 122.64(11) . . ?
C11 O6 C6 123.29(11) . . ?
O1 C1 C7 113.31(12) . . ?
O1 C1 C6 101.79(11) . . ?
C7 C1 C6 114.62(12) . . ?
O1 C1 C2 101.20(11) . . ?
C7 C1 C2 118.31(12) . . ?
C6 C1 C2 105.55(11) . . ?
O4 C2 C8 108.23(11) . . ?
O4 C2 C1 114.05(11) . . ?
C8 C2 C1 114.06(12) . . ?
O4 C2 C3 111.78(11) . . ?
C8 C2 C3 108.30(11) . . ?
C1 C2 C3 100.16(11) . . ?
F1 C3 F2 106.23(11) . . ?
F1 C3 C4 114.44(12) . . ?
F2 C3 C4 111.01(12) . . ?
F1 C3 C2 110.94(12) . . ?
F2 C3 C2 111.11(11) . . ?
C4 C3 C2 103.21(11) . . ?
O1 C4 C3 100.75(11) . . ?
O1 C4 C5 103.50(11) . . ?
C3 C4 C5 108.03(12) . . ?
C4 C5 C6 100.13(11) . . ?
C4 C5 S1 108.81(10) . . ?
C6 C5 S1 113.15(10) . . ?
O6 C6 C5 112.60(12) . . ?
O6 C6 C1 113.98(11) . . ?
C5 C6 C1 104.26(11) . . ?
O2 C8 O3 125.46(13) . . ?
O2 C8 C2 122.40(13) . . ?
O3 C8 C2 111.93(12) . . ?
O3 C9 C10 108.47(13) . . ?
O5 C11 O6 120.98(13) . . ?
O5 C11 O4 119.49(13) . . ?
O6 C11 O4 119.52(12) . . ?
C13 C12 C17 119.67(15) . . ?
C13 C12 S1 120.35(12) . . ?
C17 C12 S1 119.93(12) . . ?
C14 C13 C12 119.93(15) . . ?
C15 C14 C13 120.12(16) . . ?
C16 C15 C14 120.20(16) . . ?
C15 C16 C17 120.05(15) . . ?
C16 C17 C12 119.99(15) . . ?
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
S1 C12 1.7810(16) . ?
S1 C5 1.8166(15) . ?
F1 C3 1.3527(17) . ?
F2 C3 1.3604(17) . ?
O1 C4 1.4394(17) . ?
O1 C1 1.4430(17) . ?
O2 C8 1.1984(18) . ?
O3 C8 1.3262(18) . ?
O3 C9 1.4637(17) . ?
O4 C11 1.3508(17) . ?
O4 C2 1.4256(17) . ?
O5 C11 1.1929(17) . ?
O6 C11 1.3291(17) . ?
O6 C6 1.4412(17) . ?
C1 C7 1.502(2) . ?
C1 C6 1.542(2) . ?
C1 C2 1.5435(19) . ?
C2 C8 1.534(2) . ?
C2 C3 1.5725(19) . ?
C3 C4 1.521(2) . ?
C4 C5 1.530(2) . ?
C5 C6 1.542(2) . ?
C9 C10 1.495(2) . ?
C12 C13 1.387(2) . ?
C12 C17 1.390(2) . ?
C13 C14 1.383(2) . ?
C14 C15 1.382(2) . ?
C15 C16 1.377(2) . ?
C16 C17 1.384(2) . ?
