#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:07:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180288 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/02/7150244.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_7150244
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            'C21 H27 F2 N O6 S'
_chemical_formula_weight         459.50
_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                 98.871(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.806(2)
_cell_length_b                   22.250(6)
_cell_length_c                   11.795(3)
_cell_measurement_reflns_used    5585
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.74
_cell_measurement_theta_min      2.32
_cell_volume                     2283.4(10)
_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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16416
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0406
_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)+(0.0583P)²+0.4490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                3394
_reflns_number_total             4020
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b507131c.txt
_cod_data_source_block           11b
_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_cell_volume        2283.2(10)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7150244
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 0.29684(7) 0.62420(2) -0.02181(4) 0.04892(18) Uani 1 1 d . . .
F1 F 0.48736(13) 0.54217(5) 0.31190(9) 0.0438(3) Uani 1 1 d . . .
F2 F 0.27589(14) 0.54789(5) 0.38310(9) 0.0488(3) Uani 1 1 d . . .
N1 N 0.79618(17) 0.68601(7) 0.46646(14) 0.0402(4) Uani 1 1 d . . .
O1 O 0.19596(13) 0.64708(5) 0.23861(11) 0.0351(3) Uani 1 1 d . . .
O2 O 0.24392(14) 0.66547(7) 0.51309(11) 0.0447(4) Uani 1 1 d . . .
O3 O 0.46019(15) 0.61266(6) 0.56700(11) 0.0402(3) Uani 1 1 d . . .
O4 O 0.57684(12) 0.64333(5) 0.38849(10) 0.0293(3) Uani 1 1 d . . .
O5 O 0.56955(14) 0.72834(6) 0.49266(11) 0.0384(3) Uani 1 1 d . . .
O6 O 0.56054(14) 0.70508(6) 0.19063(11) 0.0404(3) Uani 1 1 d . . .
H6 H 0.5760 0.7269 0.1354 0.061 Uiso 1 1 calc R . .
C1 C 0.32904(19) 0.68363(8) 0.28109(15) 0.0310(4) Uani 1 1 d . . .
C2 C 0.41412(19) 0.64088(8) 0.37536(15) 0.0292(4) Uani 1 1 d . . .
C3 C 0.3670(2) 0.57859(8) 0.31936(15) 0.0331(4) Uani 1 1 d . . .
C4 C 0.2751(2) 0.59538(8) 0.20534(15) 0.0319(4) Uani 1 1 d . . .
H4 H 0.2054 0.5628 0.1698 0.038 Uiso 1 1 calc R . .
C5 C 0.3835(2) 0.61986(8) 0.12672(15) 0.0324(4) Uani 1 1 d . . .
H5 H 0.4824 0.5970 0.1361 0.039 Uiso 1 1 calc R . .
C6 C 0.4079(2) 0.68506(8) 0.17270(15) 0.0329(4) Uani 1 1 d . . .
H6A H 0.3473 0.7126 0.1158 0.039 Uiso 1 1 calc R . .
C7 C 0.2807(2) 0.74503(8) 0.31477(18) 0.0414(5) Uani 1 1 d . . .
H7A H 0.2113 0.7629 0.2507 0.062 Uiso 1 1 calc R . .
H7B H 0.3718 0.7706 0.3339 0.062 Uiso 1 1 calc R . .
H7C H 0.2277 0.7417 0.3817 0.062 Uiso 1 1 calc R . .
C8 C 0.3606(2) 0.64301(8) 0.49320(16) 0.0333(4) Uani 1 1 d . . .
C9 C 0.4332(3) 0.60910(11) 0.68506(17) 0.0542(6) Uani 1 1 d . . .
H9A H 0.3862 0.5699 0.6992 0.065 Uiso 1 1 calc R . .
H9B H 0.3625 0.6415 0.7011 0.065 Uiso 1 1 calc R . .
C10 C 0.5807(4) 0.61554(16) 0.7587(2) 0.0885(10) Uani 1 1 d . . .
H10A H 0.6528 0.5856 0.7372 0.133 Uiso 1 1 calc R . .
H10B H 0.5673 0.6094 0.8389 0.133 Uiso 1 1 calc R . .
H10C H 0.6214 0.6560 0.7497 0.133 Uiso 1 1 calc R . .
C11 C 0.6443(2) 0.68960(8) 0.45287(15) 0.0321(4) Uani 1 1 d . . .
C12 C 0.8775(2) 0.63659(10) 0.41952(19) 0.0466(5) Uani 1 1 d . . .
H12A H 0.9758 0.6518 0.3997 0.056 Uiso 1 1 calc R . .
H12B H 0.8146 0.6218 0.3481 0.056 Uiso 1 1 calc R . .
C13 C 0.9097(3) 0.58557(12) 0.5026(3) 0.0756(8) Uani 1 1 d . . .
H13A H 0.9717 0.6001 0.5735 0.113 Uiso 1 1 calc R . .
H13B H 0.9659 0.5540 0.4688 0.113 Uiso 1 1 calc R . .
H13C H 0.8124 0.5693 0.5200 0.113 Uiso 1 1 calc R . .
C14 C 0.8868(2) 0.73245(11) 0.5337(2) 0.0625(7) Uani 1 1 d . . .
H14A H 0.8355 0.7437 0.5997 0.075 Uiso 1 1 calc R . .
H14B H 0.9894 0.7160 0.5645 0.075 Uiso 1 1 calc R . .
C15 C 0.9058(3) 0.78602(13) 0.4659(3) 0.0970(11) Uani 1 1 d . . .
H15A H 0.9517 0.7748 0.3983 0.145 Uiso 1 1 calc R . .
H15B H 0.9732 0.8147 0.5126 0.145 Uiso 1 1 calc R . .
H15C H 0.8053 0.8046 0.4412 0.145 Uiso 1 1 calc R . .
C16 C 0.2385(2) 0.55060(9) -0.06201(16) 0.0379(5) Uani 1 1 d . . .
C17 C 0.2963(2) 0.49881(9) -0.00679(17) 0.0413(5) Uani 1 1 d . . .
H17 H 0.3733 0.5012 0.0590 0.050 Uiso 1 1 calc R . .
C18 C 0.2416(2) 0.44351(10) -0.04767(18) 0.0473(5) Uani 1 1 d . . .
H18 H 0.2805 0.4080 -0.0089 0.057 Uiso 1 1 calc R . .
C19 C 0.1322(3) 0.43909(11) -0.14336(18) 0.0541(6) Uani 1 1 d . . .
H19 H 0.0947 0.4009 -0.1706 0.065 Uiso 1 1 calc R . .
C20 C 0.0775(3) 0.49051(12) -0.19936(19) 0.0596(7) Uani 1 1 d . . .
H20 H 0.0035 0.4877 -0.2669 0.072 Uiso 1 1 calc R . .
C21 C 0.1282(2) 0.54589(11) -0.15905(17) 0.0503(6) Uani 1 1 d . . .
H21 H 0.0876 0.5812 -0.1978 0.060 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'
N N 0.0061 0.0033 '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
C16 S1 C5 105.92(9) . . ?
C11 N1 C14 118.65(16) . . ?
C11 N1 C12 122.83(16) . . ?
C14 N1 C12 118.50(16) . . ?
C4 O1 C1 98.27(12) . . ?
C8 O3 C9 118.04(15) . . ?
C11 O4 C2 115.91(13) . . ?
O1 C1 C7 110.77(14) . . ?
O1 C1 C6 99.66(13) . . ?
C7 C1 C6 112.41(15) . . ?
O1 C1 C2 100.23(13) . . ?
C7 C1 C2 119.29(15) . . ?
C6 C1 C2 111.93(14) . . ?
O4 C2 C8 110.22(14) . . ?
O4 C2 C3 106.14(13) . . ?
C8 C2 C3 108.14(14) . . ?
O4 C2 C1 114.80(14) . . ?
C8 C2 C1 116.40(14) . . ?
C3 C2 C1 99.90(13) . . ?
F1 C3 F2 105.67(14) . . ?
F1 C3 C4 114.24(15) . . ?
F2 C3 C4 109.61(14) . . ?
F1 C3 C2 113.60(14) . . ?
F2 C3 C2 110.57(14) . . ?
C4 C3 C2 103.21(14) . . ?
O1 C4 C3 99.90(14) . . ?
O1 C4 C5 104.82(14) . . ?
C3 C4 C5 109.27(14) . . ?
C4 C5 C6 100.76(14) . . ?
C4 C5 S1 113.46(12) . . ?
C6 C5 S1 107.74(12) . . ?
O6 C6 C1 115.12(14) . . ?
O6 C6 C5 115.33(15) . . ?
C1 C6 C5 102.35(14) . . ?
O2 C8 O3 125.88(17) . . ?
O2 C8 C2 125.60(17) . . ?
O3 C8 C2 108.39(15) . . ?
O3 C9 C10 107.7(2) . . ?
O5 C11 N1 126.15(17) . . ?
O5 C11 O4 122.26(15) . . ?
N1 C11 O4 111.58(15) . . ?
N1 C12 C13 112.04(19) . . ?
C15 C14 N1 112.2(2) . . ?
C17 C16 C21 119.11(19) . . ?
C17 C16 S1 125.33(15) . . ?
C21 C16 S1 115.54(16) . . ?
C18 C17 C16 119.70(19) . . ?
C19 C18 C17 121.0(2) . . ?
C18 C19 C20 119.2(2) . . ?
C21 C20 C19 120.8(2) . . ?
C20 C21 C16 120.2(2) . . ?
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 C16 1.759(2) . ?
S1 C5 1.8023(18) . ?
F1 C3 1.348(2) . ?
F2 C3 1.364(2) . ?
N1 C11 1.325(2) . ?
N1 C14 1.463(3) . ?
N1 C12 1.466(2) . ?
O1 C4 1.431(2) . ?
O1 C1 1.451(2) . ?
O2 C8 1.198(2) . ?
O3 C8 1.322(2) . ?
O3 C9 1.450(2) . ?
O4 C11 1.360(2) . ?
O4 C2 1.418(2) . ?
O5 C11 1.222(2) . ?
O6 C6 1.401(2) . ?
C1 C7 1.502(3) . ?
C1 C6 1.546(3) . ?
C1 C2 1.564(2) . ?
C2 C8 1.535(3) . ?
C2 C3 1.563(2) . ?
C3 C4 1.506(2) . ?
C4 C5 1.530(3) . ?
C5 C6 1.552(2) . ?
C9 C10 1.454(3) . ?
C12 C13 1.498(3) . ?
C14 C15 1.460(4) . ?
C16 C17 1.382(3) . ?
C16 C21 1.386(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.370(3) . ?
C19 C20 1.371(3) . ?
C20 C21 1.371(3) . ?
