#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/03/7150334.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_7150334
loop_
_publ_author_name
'Grainger, Richard S.'
'Tisselli, Patrizia'
'Steed, Jonathan W.'
_publ_section_title
;
 Diastereotopic group selective intramolecular cycloadditions of
 sulfenic acids to 1,4-dienes.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              151
_journal_page_last               153
_journal_paper_doi               10.1039/b314176d
_journal_volume                  2
_journal_year                    2004
_chemical_formula_sum            'C9 H15 O2.5 S'
_chemical_formula_weight         195.27
_chemical_name_common            pt062a
_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                109.079(2)
_cell_angle_beta                 92.0540(10)
_cell_angle_gamma                100.681(2)
_cell_formula_units_Z            4
_cell_length_a                   7.1304(3)
_cell_length_b                   10.9979(4)
_cell_length_c                   13.4699(6)
_cell_measurement_temperature    120(2)
_cell_volume                     975.68(7)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Hooft, 1999)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.590
_diffrn_measured_fraction_theta_max 0.590
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3808
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.9429
_exptl_absorpt_correction_T_min  0.7967
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0251P)²+0.6204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                2203
_reflns_number_total             2637
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b314176d.txt
_cod_data_source_block           PT062A.CIF
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C9 H15 O2.50 S'
_cod_database_code               7150334
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
S1 S -0.83177(9) 0.37586(6) 0.10753(5) 0.0222(2) Uani 1 1 d . . .
O1 O -0.9108(3) 0.29673(17) 0.17595(13) 0.0322(5) Uani 1 1 d . . .
C1 C -0.9910(3) 0.3157(2) -0.01356(19) 0.0216(6) Uani 1 1 d . . .
H1A H -1.0677 0.2269 -0.0240 0.026 Uiso 1 1 calc R . .
H1B H -1.0793 0.3757 -0.0125 0.026 Uiso 1 1 calc R . .
S2 S -0.35704(9) 0.37045(6) -0.47332(5) 0.0213(2) Uani 1 1 d . . .
O2 O -0.7830(2) 0.44450(15) -0.08955(13) 0.0220(4) Uani 1 1 d . . .
H2 H -0.7384 0.4475 -0.1458 0.026 Uiso 1 1 calc R . .
C2 C -0.8594(3) 0.3116(2) -0.10013(19) 0.0185(6) Uani 1 1 d . . .
H2A H -0.9318 0.2628 -0.1713 0.022 Uiso 1 1 calc R . .
H51 H -0.595(4) 0.420(3) -0.313(2) 0.050(10) Uiso 1 1 d . . .
O3 O -0.4976(2) 0.30450(16) -0.41558(13) 0.0271(4) Uani 1 1 d . . .
C3 C -0.7028(3) 0.2410(2) -0.07881(17) 0.0160(5) Uani 1 1 d . . .
O4 O -0.1361(2) 0.37481(14) -0.67030(12) 0.0191(4) Uani 1 1 d . . .
H4 H -0.0605 0.3586 -0.7171 0.023 Uiso 1 1 calc R . .
C4 C -0.7925(3) 0.0967(2) -0.10462(19) 0.0174(5) Uani 1 1 d . . .
H4A H -0.8611 0.0516 -0.1725 0.021 Uiso 1 1 calc R . .
O5 O -0.6376(3) 0.47915(19) -0.25952(14) 0.0240(4) Uani 1 1 d . . .
C5 C -0.7835(3) 0.0284(2) -0.04073(19) 0.0206(6) Uani 1 1 d . . .
H5 H -0.8440 -0.0622 -0.0661 0.025 Uiso 1 1 calc R . .
C6 C -0.6839(4) 0.0849(2) 0.0689(2) 0.0249(6) Uani 1 1 d . . .
H6A H -0.6063 0.0237 0.0801 0.030 Uiso 1 1 calc R . .
H6B H -0.7812 0.0931 0.1200 0.030 Uiso 1 1 calc R . .
C7 C -0.5536(4) 0.2195(2) 0.09034(19) 0.0226(6) Uani 1 1 d . . .
H7A H -0.5304 0.2656 0.1676 0.027 Uiso 1 1 calc R . .
H7B H -0.4283 0.2066 0.0641 0.027 Uiso 1 1 calc R . .
C8 C -0.6336(3) 0.3071(2) 0.03946(18) 0.0179(6) Uani 1 1 d . . .
H8 H -0.5268 0.3834 0.0462 0.022 Uiso 1 1 calc R . .
C9 C -0.5366(3) 0.2547(2) -0.14665(19) 0.0227(6) Uani 1 1 d . . .
H9A H -0.5860 0.2181 -0.2215 0.034 Uiso 1 1 calc R . .
H9B H -0.4412 0.2068 -0.1329 0.034 Uiso 1 1 calc R . .
H9C H -0.4765 0.3479 -0.1287 0.034 Uiso 1 1 calc R . .
C10 C -0.4185(3) 0.2779(2) -0.61278(18) 0.0198(6) Uani 1 1 d . . .
H10A H -0.5069 0.1931 -0.6227 0.024 Uiso 1 1 calc R . .
H10B H -0.4825 0.3282 -0.6475 0.024 Uiso 1 1 calc R . .
C11 C -0.2335(3) 0.2543(2) -0.65984(19) 0.0167(5) Uani 1 1 d . . .
H11 H -0.2606 0.1824 -0.7302 0.020 Uiso 1 1 calc R . .
C12 C -0.1181(3) 0.2140(2) -0.58035(18) 0.0154(5) Uani 1 1 d . . .
C13 C -0.2143(3) 0.0779(2) -0.58509(19) 0.0184(6) Uani 1 1 d . . .
H13 H -0.2471 0.0123 -0.6530 0.022 Uiso 1 1 calc R . .
C14 C -0.2568(3) 0.0424(2) -0.5022(2) 0.0216(6) Uani 1 1 d . . .
H14 H -0.3140 -0.0471 -0.5148 0.026 Uiso 1 1 calc R . .
C15 C -0.2210(4) 0.1332(2) -0.39108(19) 0.0271(6) Uani 1 1 d . . .
H15A H -0.1576 0.0921 -0.3477 0.033 Uiso 1 1 calc R . .
H15B H -0.3456 0.1462 -0.3639 0.033 Uiso 1 1 calc R . .
C16 C -0.0953(4) 0.2679(2) -0.37849(19) 0.0269(6) Uani 1 1 d . . .
H16A H -0.1216 0.3337 -0.3131 0.032 Uiso 1 1 calc R . .
H16B H 0.0412 0.2628 -0.3702 0.032 Uiso 1 1 calc R . .
C17 C -0.1276(3) 0.3154(2) -0.47122(18) 0.0188(6) Uani 1 1 d . . .
H17 H -0.0226 0.3936 -0.4618 0.023 Uiso 1 1 calc R . .
C18 C 0.0902(3) 0.2170(2) -0.6050(2) 0.0243(6) Uani 1 1 d . . .
H18A H 0.1612 0.1960 -0.5512 0.036 Uiso 1 1 calc R . .
H18B H 0.1495 0.3048 -0.6049 0.036 Uiso 1 1 calc R . .
H18C H 0.0933 0.1519 -0.6746 0.036 Uiso 1 1 calc R . .
H52 H -0.702(5) 0.517(3) -0.284(2) 0.054(11) Uiso 1 1 d . . .
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'
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
O1 S1 C1 106.96(11) . . ?
O1 S1 C8 109.32(10) . . ?
C1 S1 C8 92.57(10) . . ?
C2 C1 S1 104.86(16) . . ?
O3 S2 C10 106.37(10) . . ?
O3 S2 C17 109.95(10) . . ?
C10 S2 C17 92.51(10) . . ?
O2 C2 C1 106.35(18) . . ?
O2 C2 C3 112.08(19) . . ?
C1 C2 C3 105.81(18) . . ?
C4 C3 C8 111.17(19) . . ?
C4 C3 C9 109.48(18) . . ?
C8 C3 C9 111.00(19) . . ?
C4 C3 C2 108.36(19) . . ?
C8 C3 C2 105.45(18) . . ?
C9 C3 C2 111.30(19) . . ?
C5 C4 C3 125.5(2) . . ?
C4 C5 C6 124.0(2) . . ?
C5 C6 C7 112.5(2) . . ?
C8 C7 C6 114.3(2) . . ?
C7 C8 C3 114.62(19) . . ?
C7 C8 S1 112.92(16) . . ?
C3 C8 S1 108.11(15) . . ?
C11 C10 S2 107.25(16) . . ?
O4 C11 C10 107.64(18) . . ?
O4 C11 C12 111.63(18) . . ?
C10 C11 C12 105.78(18) . . ?
C13 C12 C18 110.20(19) . . ?
C13 C12 C17 110.54(18) . . ?
C18 C12 C17 110.70(19) . . ?
C13 C12 C11 108.59(19) . . ?
C18 C12 C11 111.38(18) . . ?
C17 C12 C11 105.32(18) . . ?
C14 C13 C12 125.3(2) . . ?
C13 C14 C15 124.4(2) . . ?
C14 C15 C16 113.1(2) . . ?
C17 C16 C15 113.8(2) . . ?
C16 C17 C12 114.37(19) . . ?
C16 C17 S2 112.71(17) . . ?
C12 C17 S2 108.34(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 O1 1.5180(17) . ?
S1 C1 1.808(3) . ?
S1 C8 1.856(2) . ?
C1 C2 1.517(3) . ?
S2 O3 1.5135(17) . ?
S2 C10 1.812(2) . ?
S2 C17 1.849(2) . ?
O2 C2 1.420(3) . ?
C2 C3 1.542(3) . ?
C3 C4 1.515(3) . ?
C3 C8 1.537(3) . ?
C3 C9 1.538(3) . ?
O4 C11 1.431(3) . ?
C4 C5 1.321(3) . ?
C5 C6 1.494(3) . ?
C6 C7 1.527(3) . ?
C7 C8 1.526(3) . ?
C10 C11 1.513(3) . ?
C11 C12 1.550(3) . ?
C12 C13 1.507(3) . ?
C12 C18 1.530(3) . ?
C12 C17 1.540(3) . ?
C13 C14 1.325(3) . ?
C14 C15 1.485(3) . ?
C15 C16 1.536(3) . ?
C16 C17 1.528(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O5 0.84 1.82 2.656(2) 171.9 .
O5 H51 O3 0.90(3) 1.81(3) 2.707(2) 177(3) .
O4 H4 O1 0.84 1.85 2.682(2) 171.4 1_654
O5 H52 O4 0.81(3) 2.01(4) 2.814(3) 174(3) 2_464
