#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:07:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180288 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/02/7150245.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_7150245
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 H20 F2 O5 S'
_chemical_formula_weight         386.40
_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                 93.158(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.875(3)
_cell_length_b                   6.5609(12)
_cell_length_c                   15.029(3)
_cell_measurement_reflns_used    2065
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.54
_cell_measurement_theta_min      2.71
_cell_volume                     1759.9(6)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0728
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12099
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0697P)²+0.3417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1545
_reflns_number_gt                2149
_reflns_number_total             3096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b507131c.txt
_cod_data_source_block           27
_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               7150245
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 0.17893(6) 0.63664(14) 0.46781(6) 0.0348(3) Uani 1 1 d . . .
F1 F 0.36018(16) 0.1113(4) 0.36103(15) 0.0765(9) Uani 1 1 d . . .
F2 F 0.39660(14) 0.4206(5) 0.38312(16) 0.0814(10) Uani 1 1 d . . .
O1 O 0.21602(14) 0.2790(3) 0.32305(15) 0.0333(6) Uani 1 1 d . . .
O2 O 0.36387(15) 0.5145(5) 0.21746(17) 0.0503(8) Uani 1 1 d . . .
O3 O 0.35193(15) 0.2843(4) 0.10780(16) 0.0470(7) Uani 1 1 d . . .
O4 O 0.19935(15) 0.5473(4) 0.55239(15) 0.0417(7) Uani 1 1 d . . .
O5 O 0.16854(16) 0.8516(4) 0.46297(16) 0.0453(7) Uani 1 1 d . . .
C1 C 0.2382(2) 0.4158(5) 0.2542(2) 0.0284(8) Uani 1 1 d . . .
C1' C 0.1880(2) 0.3909(5) 0.1726(2) 0.0361(9) Uani 1 1 d . . .
H1'1 H 0.1884 0.2481 0.1535 0.054 Uiso 1 1 calc R . .
H1'2 H 0.2058 0.4775 0.1250 0.054 Uiso 1 1 calc R . .
H1'3 H 0.1369 0.4307 0.1855 0.054 Uiso 1 1 calc R . .
C2 C 0.3209(2) 0.3552(6) 0.2495(2) 0.0372(9) Uani 1 1 d . . .
C3 C 0.3396(2) 0.3099(7) 0.3485(3) 0.0471(11) Uani 1 1 d . . .
C4 C 0.2673(2) 0.3460(6) 0.3921(2) 0.0394(10) Uani 1 1 d . . .
H4 H 0.2631 0.2724 0.4499 0.047 Uiso 1 1 calc R . .
C5 C 0.2518(2) 0.5734(5) 0.3969(2) 0.0342(9) Uani 1 1 d . . .
H5 H 0.2988 0.6463 0.4175 0.041 Uiso 1 1 calc R . .
C6 C 0.2340(2) 0.6195(5) 0.3002(2) 0.0311(9) Uani 1 1 d . . .
C6' C 0.2171(2) 0.7938(6) 0.2639(3) 0.0466(11) Uani 1 1 d . . .
H6'1 H 0.2149 0.9125 0.2999 0.056 Uiso 1 1 calc R . .
H6'2 H 0.2070 0.8029 0.2013 0.056 Uiso 1 1 calc R . .
C7 C 0.3356(2) 0.1803(6) 0.1863(2) 0.0435(10) Uani 1 1 d . . .
H7A H 0.3785 0.0961 0.2088 0.052 Uiso 1 1 calc R . .
H7B H 0.2908 0.0924 0.1767 0.052 Uiso 1 1 calc R . .
C8 C 0.3941(2) 0.4555(7) 0.1343(3) 0.0517(12) Uani 1 1 d . . .
C9 C 0.4758(3) 0.4059(10) 0.1495(4) 0.089(2) Uani 1 1 d . . .
H9A H 0.4824 0.3062 0.1978 0.134 Uiso 1 1 calc R . .
H9B H 0.5036 0.5304 0.1657 0.134 Uiso 1 1 calc R . .
H9C H 0.4947 0.3488 0.0948 0.134 Uiso 1 1 calc R . .
C10 C 0.3783(3) 0.6233(8) 0.0687(3) 0.0753(16) Uani 1 1 d . . .
H10A H 0.3938 0.5808 0.0099 0.113 Uiso 1 1 calc R . .
H10B H 0.4064 0.7455 0.0879 0.113 Uiso 1 1 calc R . .
H10C H 0.3246 0.6537 0.0652 0.113 Uiso 1 1 calc R . .
C11 C 0.0981(2) 0.5175(5) 0.4238(2) 0.0335(9) Uani 1 1 d . . .
C12 C 0.0825(2) 0.3216(6) 0.4485(2) 0.0421(10) Uani 1 1 d . . .
H12 H 0.1155 0.2507 0.4894 0.050 Uiso 1 1 calc R . .
C13 C 0.0189(3) 0.2298(7) 0.4136(3) 0.0512(12) Uani 1 1 d . . .
H13 H 0.0077 0.0937 0.4298 0.061 Uiso 1 1 calc R . .
C14 C -0.0285(3) 0.3333(7) 0.3554(3) 0.0548(12) Uani 1 1 d . . .
H14 H -0.0727 0.2683 0.3315 0.066 Uiso 1 1 calc R . .
C15 C -0.0134(2) 0.5287(8) 0.3312(3) 0.0520(12) Uani 1 1 d . . .
H15 H -0.0471 0.5994 0.2911 0.062 Uiso 1 1 calc R . .
C16 C 0.0504(2) 0.6231(6) 0.3649(2) 0.0417(10) Uani 1 1 d . . .
H16 H 0.0616 0.7587 0.3479 0.050 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
O5 S1 O4 118.55(15) . . ?
O5 S1 C11 108.80(18) . . ?
O4 S1 C11 108.65(17) . . ?
O5 S1 C5 107.37(17) . . ?
O4 S1 C5 106.15(16) . . ?
C11 S1 C5 106.71(17) . . ?
C4 O1 C1 98.1(3) . . ?
C2 O2 C8 109.7(3) . . ?
C8 O3 C7 106.5(3) . . ?
O1 C1 C1' 110.3(3) . . ?
O1 C1 C6 101.6(3) . . ?
C1' C1 C6 115.6(3) . . ?
O1 C1 C2 100.1(3) . . ?
C1' C1 C2 118.1(3) . . ?
C6 C1 C2 108.8(3) . . ?
O2 C2 C7 103.4(3) . . ?
O2 C2 C3 112.6(3) . . ?
C7 C2 C3 115.0(3) . . ?
O2 C2 C1 111.7(3) . . ?
C7 C2 C1 115.0(3) . . ?
C3 C2 C1 99.4(3) . . ?
F2 C3 F1 105.8(3) . . ?
F2 C3 C4 113.7(3) . . ?
F1 C3 C4 108.8(4) . . ?
F2 C3 C2 113.2(4) . . ?
F1 C3 C2 111.2(3) . . ?
C4 C3 C2 104.2(3) . . ?
O1 C4 C3 99.7(3) . . ?
O1 C4 C5 103.2(3) . . ?
C3 C4 C5 109.8(3) . . ?
C6 C5 C4 100.5(3) . . ?
C6 C5 S1 114.2(3) . . ?
C4 C5 S1 113.5(3) . . ?
C6' C6 C5 128.1(3) . . ?
C6' C6 C1 127.3(3) . . ?
C5 C6 C1 104.6(3) . . ?
O3 C7 C2 102.0(3) . . ?
O3 C8 O2 104.0(3) . . ?
O3 C8 C10 108.9(4) . . ?
O2 C8 C10 108.0(4) . . ?
O3 C8 C9 111.9(4) . . ?
O2 C8 C9 109.5(4) . . ?
C10 C8 C9 113.9(4) . . ?
C12 C11 C16 121.0(4) . . ?
C12 C11 S1 119.7(3) . . ?
C16 C11 S1 119.3(3) . . ?
C13 C12 C11 119.2(4) . . ?
C12 C13 C14 120.1(4) . . ?
C15 C14 C13 120.9(4) . . ?
C14 C15 C16 120.0(4) . . ?
C15 C16 C11 118.8(4) . . ?
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 O5 1.424(2) . ?
S1 O4 1.429(2) . ?
S1 C11 1.741(4) . ?
S1 C5 1.777(4) . ?
F1 C3 1.364(5) . ?
F2 C3 1.334(5) . ?
O1 C4 1.416(4) . ?
O1 C1 1.442(4) . ?
O2 C2 1.398(4) . ?
O2 C8 1.441(4) . ?
O3 C8 1.399(5) . ?
O3 C7 1.407(4) . ?
C1 C1' 1.488(5) . ?
C1 C6 1.508(5) . ?
C1 C2 1.537(5) . ?
C2 C7 1.522(5) . ?
C2 C3 1.535(5) . ?
C3 C4 1.501(5) . ?
C4 C5 1.519(5) . ?
C5 C6 1.501(5) . ?
C6 C6' 1.295(5) . ?
C8 C10 1.495(6) . ?
C8 C9 1.501(6) . ?
C11 C12 1.370(5) . ?
C11 C16 1.382(5) . ?
C12 C13 1.365(6) . ?
C13 C14 1.365(6) . ?
C14 C15 1.364(6) . ?
C15 C16 1.369(6) . ?
