#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:03:23 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180329 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/43/7154360.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_7154360
loop_
_publ_author_name
'Brant, Michael G.'
'Friedmann, Jordan N.'
'Bohlken, Connor G.'
'Oliver, Allen G.'
'Wulff, Jeremy E.'
_publ_section_title
;
 Diastereoselective tandem reactions of substituted 3-sulfolenes with
 bis-vinyl ketones leading to highly functionalized bicyclic and tricyclic
 frameworks.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4581
_journal_page_last               4588
_journal_paper_doi               10.1039/c5ob00387c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C23 H23 Cl O5 S'
_chemical_formula_sum            'C23 H23 Cl O5 S'
_chemical_formula_weight         446.92
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2014-09-18 deposited with the CCDC.
2015-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 120.899(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.4489(15)
_cell_length_b                   15.1178(15)
_cell_length_c                   14.8599(12)
_cell_measurement_reflns_used    5628
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.69
_cell_measurement_theta_min      2.21
_cell_volume                     4134.6(6)
_computing_cell_refinement       'Bruker SAINT v8.32B'
_computing_data_collection       'Bruker APEX-II v2013-10.0'
_computing_data_reduction        'Bruker SAINT v8.32B'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of ω and φ-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  0.0713
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31813
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_min         1.743
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8379
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0334P)²+3.0297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0898
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3173
_reflns_number_total             4240
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ob00387c2.cif
_cod_data_source_block           uvic1407a
_cod_depositor_comments
'Adding full bibliography for 7154360--7154364.cif.'
_cod_database_code               7154360
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.45773(3) 0.66809(4) 0.61442(4) 0.02306(17) Uani 0.9426(17) 1 d . . P A
1
Cl1A Cl 0.3822(7) 0.7726(9) 0.7004(10) 0.055(4) Uiso 0.0574(17) 1 d . . P A 2
S1 S 0.35814(3) 0.50892(3) 0.71437(4) 0.01797(13) Uani 1 1 d . . . . .
O1 O 0.29030(8) 0.46372(9) 0.67466(11) 0.0255(4) Uani 1 1 d . . . . .
O2 O 0.42013(8) 0.47304(10) 0.80622(11) 0.0271(4) Uani 1 1 d . . . . .
O3 O 0.24675(8) 0.63388(9) 0.46957(12) 0.0198(3) Uani 1 1 d . . . . .
H3O H 0.2163(15) 0.6087(19) 0.417(2) 0.053(9) Uiso 1 1 d . . . . .
O4 O 0.40360(8) 0.13636(9) 0.44181(12) 0.0277(4) Uani 1 1 d . . . . .
O5 O 0.37885(8) 1.03284(9) 0.17833(11) 0.0258(4) Uani 1 1 d . . . . .
C1 C 0.38016(10) 0.52509(12) 0.61413(14) 0.0155(4) Uani 1 1 d . . . . .
H1 H 0.4310 0.5065 0.6408 0.019 Uiso 1 1 calc R U . . .
C2 C 0.32965(10) 0.47834(12) 0.50963(14) 0.0156(4) Uani 1 1 d . . . . .
H2 H 0.2811 0.4730 0.5017 0.019 Uiso 1 1 calc R U . . .
C3 C 0.32473(11) 0.54695(12) 0.43059(15) 0.0159(4) Uani 1 1 d . . . . .
H3A H 0.3693 0.5476 0.4275 0.019 Uiso 1 1 calc R U . . .
H3B H 0.2833 0.5348 0.3604 0.019 Uiso 1 1 calc R U . . .
C4 C 0.31475(10) 0.63397(13) 0.47268(15) 0.0162(4) Uani 1 1 d . . . . .
C5 C 0.37297(11) 0.62547(13) 0.59199(15) 0.0167(4) Uani 1 1 d . . . . .
H5 H 0.4199 0.6483 0.6041 0.020 Uiso 0.0574(17) 1 calc R U P A 2
C6 C 0.35532(11) 0.67098(14) 0.66536(15) 0.0211(5) Uani 1 1 d . . . . .
H6 H 0.3501 0.7328 0.6645 0.025 Uiso 0.9426(17) 1 calc R U P A 1
C7 C 0.34746(11) 0.62091(14) 0.73120(15) 0.0202(5) Uani 1 1 d . . . . .
H7 H 0.3373 0.6429 0.7815 0.024 Uiso 1 1 calc R U . . .
C8 C 0.35336(11) 0.38747(13) 0.49758(14) 0.0156(4) Uani 1 1 d . . . . .
C9 C 0.30214(11) 0.32052(13) 0.45385(15) 0.0198(4) Uani 1 1 d . . . . .
H9 H 0.2541 0.3319 0.4363 0.024 Uiso 1 1 calc R U . . .
C10 C 0.31994(11) 0.23783(13) 0.43552(16) 0.0231(5) Uani 1 1 d . . . . .
H10 H 0.2843 0.1935 0.4051 0.028 Uiso 1 1 calc R U . . .
C11 C 0.39054(11) 0.22035(13) 0.46216(15) 0.0185(4) Uani 1 1 d . . . . .
C12 C 0.44304(11) 0.28569(13) 0.50718(15) 0.0198(4) Uani 1 1 d . . . . .
H12 H 0.4913 0.2737 0.5264 0.024 Uiso 1 1 calc R U . . .
C13 C 0.42378(11) 0.36871(13) 0.52354(15) 0.0191(4) Uani 1 1 d . . . . .
H13 H 0.4592 0.4133 0.5529 0.023 Uiso 1 1 calc R U . . .
C14 C 0.47332(12) 0.11902(15) 0.4572(2) 0.0372(6) Uani 1 1 d . . . . .
H14A H 0.4744 0.0596 0.4334 0.056 Uiso 1 1 calc R U . . .
H14B H 0.5096 0.1243 0.5311 0.056 Uiso 1 1 calc R U . . .
H14C H 0.4837 0.1613 0.4176 0.056 Uiso 1 1 calc R U . . .
C15 C 0.32061(11) 0.71661(13) 0.42314(15) 0.0181(4) Uani 1 1 d . . . . .
H15 H 0.3076 0.7697 0.4421 0.022 Uiso 1 1 calc R U . . .
C16 C 0.34253(11) 0.72192(13) 0.35480(15) 0.0187(4) Uani 1 1 d . . . . .
H16 H 0.3529 0.6682 0.3332 0.022 Uiso 1 1 calc R U . . .
C17 C 0.35238(10) 0.80292(13) 0.30919(14) 0.0167(4) Uani 1 1 d . . . . .
C18 C 0.33298(10) 0.88624(13) 0.32723(14) 0.0166(4) Uani 1 1 d . . . . .
H18 H 0.3123 0.8913 0.3695 0.020 Uiso 1 1 calc R U . . .
C19 C 0.34363(10) 0.96091(13) 0.28436(15) 0.0187(4) Uani 1 1 d . . . . .
H19 H 0.3310 1.0166 0.2983 0.022 Uiso 1 1 calc R U . . .
C20 C 0.37302(11) 0.95436(13) 0.22051(15) 0.0193(4) Uani 1 1 d . . . . .
C21 C 0.39381(11) 0.87273(14) 0.20255(16) 0.0216(5) Uani 1 1 d . . . . .
H21 H 0.4149 0.8679 0.1608 0.026 Uiso 1 1 calc R U . . .
C22 C 0.38301(11) 0.79830(14) 0.24698(15) 0.0205(5) Uani 1 1 d . . . . .
H22 H 0.3969 0.7428 0.2345 0.025 Uiso 1 1 calc R U . . .
C23 C 0.40685(14) 1.02841(17) 0.1100(2) 0.0387(6) Uani 1 1 d . . . . .
H23A H 0.4095 1.0875 0.0869 0.058 Uiso 1 1 calc R U . . .
H23B H 0.3751 0.9922 0.0496 0.058 Uiso 1 1 calc R U . . .
H23C H 0.4550 1.0024 0.1469 0.058 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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
O1 S1 O2 117.42(9)
O1 S1 C7 109.99(9)
O2 S1 C7 110.87(9)
O1 S1 C1 111.56(9)
O2 S1 C1 109.29(9)
C7 S1 C1 95.55(9)
C11 O4 C14 117.10(16)
C20 O5 C23 117.05(17)
C2 C1 C5 107.19(15)
C2 C1 S1 115.27(13)
C5 C1 S1 105.70(13)
C8 C2 C3 114.91(16)
C8 C2 C1 115.71(16)
C3 C2 C1 101.49(15)
C4 C3 C2 103.89(15)
O3 C4 C15 109.12(15)
O3 C4 C3 109.99(16)
C15 C4 C3 117.27(16)
O3 C4 C5 104.06(15)
C15 C4 C5 114.13(16)
C3 C4 C5 101.33(15)
C6 C5 C1 109.42(16)
C6 C5 C4 115.84(16)
C1 C5 C4 104.87(15)
C6 C5 Cl1 108.18(13)
C1 C5 Cl1 109.46(13)
C4 C5 Cl1 108.94(13)
C7 C6 C5 117.10(18)
C7 C6 Cl1A 117.7(5)
C5 C6 Cl1A 119.1(5)
C6 C7 S1 112.08(16)
C13 C8 C9 118.06(18)
C13 C8 C2 122.74(18)
C9 C8 C2 119.12(18)
C10 C9 C8 121.54(19)
C9 C10 C11 119.53(19)
O4 C11 C10 115.71(18)
O4 C11 C12 124.13(18)
C10 C11 C12 120.16(18)
C13 C12 C11 119.38(19)
C12 C13 C8 121.32(19)
C16 C15 C4 125.77(18)
C15 C16 C17 126.72(19)
C22 C17 C18 117.70(18)
C22 C17 C16 119.81(18)
C18 C17 C16 122.49(18)
C19 C18 C17 121.10(19)
C18 C19 C20 120.12(19)
O5 C20 C21 124.53(18)
O5 C20 C19 115.43(18)
C21 C20 C19 120.03(18)
C22 C21 C20 118.93(19)
C21 C22 C17 122.09(19)
C4 O3 H3O 110(2)
C2 C1 H1 109.5
C5 C1 H1 109.5
S1 C1 H1 109.5
C8 C2 H2 108.1
C3 C2 H2 108.1
C1 C2 H2 108.1
C4 C3 H3A 111.0
C2 C3 H3A 111.0
C4 C3 H3B 111.0
C2 C3 H3B 111.0
H3A C3 H3B 109.0
C6 C5 H5 108.8
C1 C5 H5 108.8
C4 C5 H5 108.8
C7 C6 H6 121.4
C5 C6 H6 121.4
C6 C7 H7 124.0
S1 C7 H7 124.0
C10 C9 H9 119.2
C8 C9 H9 119.2
C9 C10 H10 120.2
C11 C10 H10 120.2
C13 C12 H12 120.3
C11 C12 H12 120.3
C12 C13 H13 119.3
C8 C13 H13 119.3
O4 C14 H14A 109.5
O4 C14 H14B 109.5
H14A C14 H14B 109.5
O4 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C16 C15 H15 117.1
C4 C15 H15 117.1
C15 C16 H16 116.6
C17 C16 H16 116.6
C19 C18 H18 119.5
C17 C18 H18 119.5
C18 C19 H19 119.9
C20 C19 H19 119.9
C22 C21 H21 120.5
C20 C21 H21 120.5
C21 C22 H22 119.0
C17 C22 H22 119.0
O5 C23 H23A 109.5
O5 C23 H23B 109.5
H23A C23 H23B 109.5
O5 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.791(2)
Cl1A C6 1.630(13)
S1 O1 1.4319(15)
S1 O2 1.4357(15)
S1 C7 1.744(2)
S1 C1 1.7956(19)
O3 C4 1.435(2)
O4 C11 1.367(2)
O4 C14 1.416(3)
O5 C20 1.377(2)
O5 C23 1.422(3)
C1 C2 1.535(3)
C1 C5 1.544(3)
C2 C8 1.507(3)
C2 C3 1.530(3)
C3 C4 1.518(3)
C4 C15 1.488(3)
C4 C5 1.564(3)
C5 C6 1.493(3)
C6 C7 1.314(3)
C8 C13 1.383(3)
C8 C9 1.386(3)
C9 C10 1.375(3)
C10 C11 1.380(3)
C11 C12 1.385(3)
C12 C13 1.381(3)
C15 C16 1.322(3)
C16 C17 1.467(3)
C17 C22 1.384(3)
C17 C18 1.395(3)
C18 C19 1.372(3)
C19 C20 1.386(3)
C20 C21 1.384(3)
C21 C22 1.383(3)
O3 H3O 0.81(3)
C1 H1 0.9900
C2 H2 0.9900
C3 H3A 0.9800
C3 H3B 0.9800
C5 H5 0.9900
C6 H6 0.9400
C7 H7 0.9400
C9 H9 0.9400
C10 H10 0.9400
C12 H12 0.9400
C13 H13 0.9400
C14 H14A 0.9700
C14 H14B 0.9700
C14 H14C 0.9700
C15 H15 0.9400
C16 H16 0.9400
C18 H18 0.9400
C19 H19 0.9400
C21 H21 0.9400
C22 H22 0.9400
C23 H23A 0.9700
C23 H23B 0.9700
C23 H23C 0.9700
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 H3O O5 0.81(3) 2.13(3) 2.888(2) 157(3) 4_545
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
O1 S1 C1 C2 -7.74(17)
O2 S1 C1 C2 123.79(14)
C7 S1 C1 C2 -121.80(14)
O1 S1 C1 C5 110.44(13)
O2 S1 C1 C5 -118.04(13)
C7 S1 C1 C5 -3.63(14)
C5 C1 C2 C8 149.99(16)
S1 C1 C2 C8 -92.67(18)
C5 C1 C2 C3 24.90(19)
S1 C1 C2 C3 142.24(13)
C8 C2 C3 C4 -169.32(16)
C1 C2 C3 C4 -43.69(18)
C2 C3 C4 O3 -64.71(18)
C2 C3 C4 C15 169.87(16)
C2 C3 C4 C5 44.95(18)
C2 C1 C5 C6 126.88(17)
S1 C1 C5 C6 3.43(18)
C2 C1 C5 C4 2.0(2)
S1 C1 C5 C4 -121.44(14)
C2 C1 C5 Cl1 -114.74(14)
S1 C1 C5 Cl1 121.82(11)
O3 C4 C5 C6 -34.9(2)
C15 C4 C5 C6 84.0(2)
C3 C4 C5 C6 -149.04(17)
O3 C4 C5 C1 85.86(17)
C15 C4 C5 C1 -155.32(16)
C3 C4 C5 C1 -28.32(18)
O3 C4 C5 Cl1 -157.04(12)
C15 C4 C5 Cl1 -38.2(2)
C3 C4 C5 Cl1 88.78(15)
C1 C5 C6 C7 -1.6(2)
C4 C5 C6 C7 116.7(2)
Cl1 C5 C6 C7 -120.74(18)
C1 C5 C6 Cl1A 150.4(5)
C4 C5 C6 Cl1A -91.3(6)
Cl1 C5 C6 Cl1A 31.3(6)
C5 C6 C7 S1 -1.3(2)
Cl1A C6 C7 S1 -153.7(5)
O1 S1 C7 C6 -112.34(16)
O2 S1 C7 C6 116.12(16)
C1 S1 C7 C6 3.02(17)
C3 C2 C8 C13 71.7(2)
C1 C2 C8 C13 -46.2(3)
C3 C2 C8 C9 -105.0(2)
C1 C2 C8 C9 137.16(18)
C13 C8 C9 C10 -0.6(3)
C2 C8 C9 C10 176.23(18)
C8 C9 C10 C11 0.7(3)
C14 O4 C11 C10 173.1(2)
C14 O4 C11 C12 -7.4(3)
C9 C10 C11 O4 179.64(18)
C9 C10 C11 C12 0.1(3)
O4 C11 C12 C13 179.47(18)
C10 C11 C12 C13 -1.0(3)
C11 C12 C13 C8 1.2(3)
C9 C8 C13 C12 -0.4(3)
C2 C8 C13 C12 -177.07(18)
O3 C4 C15 C16 -134.8(2)
C3 C4 C15 C16 -8.9(3)
C5 C4 C15 C16 109.3(2)
C4 C15 C16 C17 -176.54(18)
C15 C16 C17 C22 173.2(2)
C15 C16 C17 C18 -5.8(3)
C22 C17 C18 C19 0.3(3)
C16 C17 C18 C19 179.27(18)
C17 C18 C19 C20 1.1(3)
C23 O5 C20 C21 1.4(3)
C23 O5 C20 C19 -178.25(19)
C18 C19 C20 O5 177.62(17)
C18 C19 C20 C21 -2.0(3)
O5 C20 C21 C22 -177.97(18)
C19 C20 C21 C22 1.6(3)
C20 C21 C22 C17 -0.3(3)
C18 C17 C22 C21 -0.7(3)
C16 C17 C22 C21 -179.68(18)
