#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025687.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_4025687
loop_
_publ_author_name
'Michael G. Brant'
'Caleb M. Bromba'
'Jeremy E. Wulff'
_publ_contact_author_address
'Dept. of Chemistry.  University of Victoria.'
_publ_contact_author_email       wulff@uvic.ca
_publ_contact_author_name        'Jeremy Wulff'
_publ_section_title
;
 Tandem Vinylogous 1,2-Addition/Anionic Oxy-Cope Reaction Leading from
 Butadiene Sulfone to an Orthogonally Functionalized Bicycle
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6312
_journal_page_last               6315
_journal_paper_doi               10.1021/jo101389c
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C18 H24 O3 S'
_chemical_formula_sum            'C18 H24 O3 S'
_chemical_formula_weight         320.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.2547(2)
_cell_length_b                   27.5395(5)
_cell_length_c                   9.9291(2)
_cell_measurement_reflns_used    5882
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.41
_cell_measurement_theta_min      3.21
_cell_volume                     3350.96(11)
_computing_cell_refinement       'Bruker SAINT v7.60A'
_computing_data_collection       'Bruker APEX-II v2009-7'
_computing_data_reduction        'Bruker SAINT v7.60A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            30135
_diffrn_reflns_theta_full        69.65
_diffrn_reflns_theta_max         69.65
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    1.794
_exptl_absorpt_correction_T_max  0.8135
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0400
_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)+(0.0502P)²+2.7070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                2614
_reflns_number_total             3131
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101389c_si_002.cif
_cod_data_source_block           uvic04a
_cod_database_code               4025687
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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 0.69803(4) 0.440607(16) 0.54443(5) 0.01972(14) Uani 1 1 d . . .
O1 O 0.68501(11) 0.48142(5) 0.45328(13) 0.0246(3) Uani 1 1 d . . .
O2 O 0.80839(11) 0.42346(5) 0.56654(14) 0.0259(3) Uani 1 1 d . . .
O3 O 0.40208(10) 0.42161(5) 0.61440(13) 0.0236(3) Uani 1 1 d . . .
H3 H 0.3654 0.4470 0.6026 0.028 Uiso 1 1 calc R . .
C1 C 0.61509(15) 0.39005(6) 0.49300(19) 0.0208(4) Uani 1 1 d . . .
H1A H 0.5461 0.4026 0.4520 0.025 Uiso 1 1 calc R . .
C2 C 0.58793(15) 0.36505(7) 0.62645(19) 0.0223(4) Uani 1 1 d . . .
H2A H 0.6492 0.3438 0.6539 0.027 Uiso 1 1 calc R . .
H2B H 0.5219 0.3447 0.6157 0.027 Uiso 1 1 calc R . .
C3 C 0.56788(15) 0.40411(7) 0.73533(19) 0.0207(4) Uani 1 1 d . . .
H3A H 0.5916 0.3909 0.8245 0.025 Uiso 1 1 calc R . .
C4 C 0.63470(16) 0.45107(7) 0.70457(19) 0.0208(4) Uani 1 1 d . . .
H4A H 0.6925 0.4553 0.7748 0.025 Uiso 1 1 calc R . .
C5 C 0.55501(15) 0.49434(7) 0.71094(19) 0.0225(4) Uani 1 1 d . . .
H5A H 0.5262 0.5008 0.6184 0.027 Uiso 1 1 calc R . .
C6 C 0.46275(16) 0.47401(7) 0.7980(2) 0.0240(4) Uani 1 1 d . . .
H6A H 0.3950 0.4931 0.7858 0.029 Uiso 1 1 calc R . .
H6B H 0.4831 0.4744 0.8945 0.029 Uiso 1 1 calc R . .
C7 C 0.44792(15) 0.42190(7) 0.74735(19) 0.0214(4) Uani 1 1 d . . .
C8 C 0.38276(15) 0.39013(7) 0.8413(2) 0.0234(4) Uani 1 1 d . . .
H8A H 0.4049 0.3894 0.9329 0.028 Uiso 1 1 calc R . .
C9 C 0.29764(16) 0.36322(7) 0.8079(2) 0.0251(4) Uani 1 1 d . . .
H9A H 0.2761 0.3634 0.7160 0.030 Uiso 1 1 calc R . .
C10 C 0.23224(17) 0.33246(8) 0.9026(2) 0.0316(5) Uani 1 1 d . . .
H10A H 0.2358 0.2985 0.8737 0.047 Uiso 1 1 calc R . .
H10B H 0.1561 0.3434 0.9021 0.047 Uiso 1 1 calc R . .
H10C H 0.2620 0.3354 0.9938 0.047 Uiso 1 1 calc R . .
C11 C 0.67568(16) 0.35910(7) 0.3883(2) 0.0256(4) Uani 1 1 d . . .
H11A H 0.7045 0.3805 0.3166 0.031 Uiso 1 1 calc R . .
H11B H 0.7385 0.3429 0.4321 0.031 Uiso 1 1 calc R . .
C12 C 0.60244(16) 0.32104(7) 0.3258(2) 0.0248(4) Uani 1 1 d . . .
C13 C 0.59100(18) 0.27487(8) 0.3815(2) 0.0316(5) Uani 1 1 d . . .
H13A H 0.6312 0.2664 0.4599 0.038 Uiso 1 1 calc R . .
C14 C 0.5214(2) 0.24119(8) 0.3234(2) 0.0379(6) Uani 1 1 d . . .
H14A H 0.5152 0.2097 0.3616 0.045 Uiso 1 1 calc R . .
C15 C 0.46121(19) 0.25290(9) 0.2110(2) 0.0367(5) Uani 1 1 d . . .
H15A H 0.4127 0.2298 0.1726 0.044 Uiso 1 1 calc R . .
C16 C 0.47189(18) 0.29851(8) 0.1544(2) 0.0343(5) Uani 1 1 d . . .
H16A H 0.4304 0.3068 0.0769 0.041 Uiso 1 1 calc R . .
C17 C 0.54295(17) 0.33215(8) 0.2101(2) 0.0285(5) Uani 1 1 d . . .
H17A H 0.5512 0.3631 0.1691 0.034 Uiso 1 1 calc R . .
C18 C 0.60727(18) 0.54064(7) 0.7655(2) 0.0305(5) Uani 1 1 d . . .
H18A H 0.6655 0.5512 0.7045 0.046 Uiso 1 1 calc R . .
H18B H 0.6380 0.5343 0.8549 0.046 Uiso 1 1 calc R . .
H18C H 0.5519 0.5662 0.7721 0.046 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O2 S1 O1 116.69(8) . . ?
O2 S1 C4 108.78(9) . . ?
O1 S1 C4 112.39(8) . . ?
O2 S1 C1 108.56(8) . . ?
O1 S1 C1 111.12(9) . . ?
C4 S1 C1 97.56(9) . . ?
C2 C1 C11 116.22(16) . . ?
C2 C1 S1 103.03(13) . . ?
C11 C1 S1 110.41(13) . . ?
C1 C2 C3 109.12(15) . . ?
C2 C3 C7 115.07(15) . . ?
C2 C3 C4 110.89(15) . . ?
C7 C3 C4 104.48(15) . . ?
C5 C4 C3 107.46(15) . . ?
C5 C4 S1 115.77(13) . . ?
C3 C4 S1 105.52(12) . . ?
C18 C5 C6 114.55(17) . . ?
C18 C5 C4 113.23(16) . . ?
C6 C5 C4 102.03(15) . . ?
C5 C6 C7 104.19(15) . . ?
O3 C7 C8 111.02(15) . . ?
O3 C7 C6 110.72(15) . . ?
C8 C7 C6 113.80(16) . . ?
O3 C7 C3 107.34(14) . . ?
C8 C7 C3 111.44(15) . . ?
C6 C7 C3 102.03(15) . . ?
C9 C8 C7 126.04(18) . . ?
C8 C9 C10 125.60(19) . . ?
C12 C11 C1 112.05(16) . . ?
C13 C12 C17 118.35(19) . . ?
C13 C12 C11 121.91(19) . . ?
C17 C12 C11 119.74(18) . . ?
C14 C13 C12 120.5(2) . . ?
C15 C14 C13 120.7(2) . . ?
C14 C15 C16 119.5(2) . . ?
C15 C16 C17 120.3(2) . . ?
C16 C17 C12 120.7(2) . . ?
C7 O3 H3 109.5 . . ?
C2 C1 H1A 109.0 . . ?
C11 C1 H1A 109.0 . . ?
S1 C1 H1A 109.0 . . ?
C1 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
C3 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C2 C3 H3A 108.7 . . ?
C7 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
S1 C4 H4A 109.3 . . ?
C18 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C5 C6 H6A 110.9 . . ?
C7 C6 H6A 110.9 . . ?
C5 C6 H6B 110.9 . . ?
C7 C6 H6B 110.9 . . ?
H6A C6 H6B 108.9 . . ?
C9 C8 H8A 117.0 . . ?
C7 C8 H8A 117.0 . . ?
C8 C9 H9A 117.2 . . ?
C10 C9 H9A 117.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 H11A 109.2 . . ?
C1 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C1 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C16 C17 H17A 119.7 . . ?
C12 C17 H17A 119.7 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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 O2 1.4492(14) . ?
S1 O1 1.4517(13) . ?
S1 C4 1.7927(19) . ?
S1 C1 1.7980(18) . ?
O3 C7 1.435(2) . ?
C1 C2 1.530(3) . ?
C1 C11 1.536(3) . ?
C2 C3 1.545(3) . ?
C3 C7 1.554(3) . ?
C3 C4 1.561(3) . ?
C4 C5 1.542(3) . ?
C5 C6 1.529(3) . ?
C5 C18 1.526(3) . ?
C6 C7 1.531(3) . ?
C7 C8 1.508(3) . ?
C8 C9 1.322(3) . ?
C9 C10 1.498(3) . ?
C11 C12 1.513(3) . ?
C12 C13 1.394(3) . ?
C12 C17 1.394(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.376(3) . ?
C15 C16 1.382(3) . ?
C16 C17 1.387(3) . ?
O3 H3 0.8400 . ?
C1 H1A 1.0000 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 1.0000 . ?
C4 H4A 1.0000 . ?
C5 H5A 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
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
O3 H3 O1 0.84 2.14 2.9534(18) 163.4 5_666
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C1 C2 80.87(13) . . . . ?
O1 S1 C1 C2 -149.51(12) . . . . ?
C4 S1 C1 C2 -31.91(13) . . . . ?
O2 S1 C1 C11 -43.88(16) . . . . ?
O1 S1 C1 C11 85.74(15) . . . . ?
C4 S1 C1 C11 -156.66(14) . . . . ?
C11 C1 C2 C3 159.20(16) . . . . ?
S1 C1 C2 C3 38.34(17) . . . . ?
C1 C2 C3 C7 89.44(19) . . . . ?
C1 C2 C3 C4 -28.9(2) . . . . ?
C2 C3 C4 C5 128.97(16) . . . . ?
C7 C3 C4 C5 4.44(18) . . . . ?
C2 C3 C4 S1 4.90(18) . . . . ?
C7 C3 C4 S1 -119.64(13) . . . . ?
O2 S1 C4 C5 144.79(14) . . . . ?
O1 S1 C4 C5 14.00(17) . . . . ?
C1 S1 C4 C5 -102.61(15) . . . . ?
O2 S1 C4 C3 -96.54(13) . . . . ?
O1 S1 C4 C3 132.67(12) . . . . ?
C1 S1 C4 C3 16.06(14) . . . . ?
C3 C4 C5 C18 145.75(17) . . . . ?
S1 C4 C5 C18 -96.65(18) . . . . ?
C3 C4 C5 C6 22.12(18) . . . . ?
S1 C4 C5 C6 139.72(14) . . . . ?
C18 C5 C6 C7 -163.92(16) . . . . ?
C4 C5 C6 C7 -41.18(18) . . . . ?
C5 C6 C7 O3 -69.66(18) . . . . ?
C5 C6 C7 C8 164.48(16) . . . . ?
C5 C6 C7 C3 44.32(18) . . . . ?
C2 C3 C7 O3 -34.6(2) . . . . ?
C4 C3 C7 O3 87.24(17) . . . . ?
C2 C3 C7 C8 87.16(19) . . . . ?
C4 C3 C7 C8 -151.01(15) . . . . ?
C2 C3 C7 C6 -151.04(16) . . . . ?
C4 C3 C7 C6 -29.22(17) . . . . ?
O3 C7 C8 C9 3.1(3) . . . . ?
C6 C7 C8 C9 128.8(2) . . . . ?
C3 C7 C8 C9 -116.5(2) . . . . ?
C7 C8 C9 C10 -178.84(19) . . . . ?
C2 C1 C11 C12 72.4(2) . . . . ?
S1 C1 C11 C12 -170.74(14) . . . . ?
C1 C11 C12 C13 -89.3(2) . . . . ?
C1 C11 C12 C17 89.8(2) . . . . ?
C17 C12 C13 C14 -0.5(3) . . . . ?
C11 C12 C13 C14 178.57(19) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C12 -1.7(3) . . . . ?
C13 C12 C17 C16 1.8(3) . . . . ?
C11 C12 C17 C16 -177.29(18) . . . . ?
