#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:12:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178425 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/46/4024683.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_4024683
loop_
_publ_author_name
'Yu-Long Zhao'
'Li Chen'
'Shao-Chun Yang'
'Cui Tian'
'Qun Liu'
_publ_section_title
;
A Synthetic Strategy for Polyfunctionalized Bicyclo[3.3.1]nonanes Based on
a Tandem Three-Component [3 + 2] Cycloaddition of α-Cinnamoyl
Ketene-S,S-acetals with Oxalyl Chloride
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5622
_journal_page_last               5625
_journal_paper_doi               10.1021/jo900764s
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C28 H30 O6 S4'
_chemical_formula_weight         590.76
_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                99.850(2)
_cell_angle_beta                 97.480(2)
_cell_angle_gamma                104.845(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7052(10)
_cell_length_b                   9.8540(12)
_cell_length_c                   18.635(2)
_cell_measurement_reflns_used    5760
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      1.51
_cell_volume                     1496.8(3)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8474
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0627
_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)+(0.0709P)²+0.5773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1648
_reflns_number_gt                3867
_reflns_number_total             5760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900764s_si_001.cif
_cod_data_source_block           ra187m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024683
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 0.51931(11) 0.22007(11) 0.02878(5) 0.0619(3) Uani 1 1 d . . .
S2 S -0.37235(12) 0.19434(11) -0.27215(6) 0.0670(3) Uani 1 1 d . . .
S3 S 0.16715(12) 0.12599(13) -0.02531(6) 0.0767(3) Uani 1 1 d . . .
S4 S -0.08765(13) 0.36513(11) -0.33109(7) 0.0800(4) Uani 1 1 d . . .
O1 O 0.0472(4) 0.0017(3) -0.40685(14) 0.0824(8) Uani 1 1 d . . .
O2 O -0.5471(3) -0.3318(3) -0.44430(14) 0.0723(7) Uani 1 1 d . . .
O3 O -0.1645(3) -0.0515(3) -0.20516(14) 0.0817(8) Uani 1 1 d . . .
O4 O 0.6547(3) 0.4511(3) -0.04618(14) 0.0711(7) Uani 1 1 d . . .
O5 O 0.5758(3) 0.5557(3) -0.18099(14) 0.0729(7) Uani 1 1 d . . .
O6 O 0.3536(3) 0.3693(2) -0.20277(12) 0.0533(6) Uani 1 1 d . . .
C1 C -0.1040(8) 0.5158(5) -0.2682(5) 0.149(3) Uani 1 1 d . . .
H1A H -0.0885 0.5963 -0.2927 0.179 Uiso 1 1 calc R . .
H1B H -0.2137 0.4942 -0.2587 0.179 Uiso 1 1 calc R . .
C2 C -0.0382(7) 0.2828(6) 0.0059(4) 0.134(2) Uani 1 1 d . . .
H2A H -0.1039 0.3407 -0.0100 0.201 Uiso 1 1 calc R . .
H2B H 0.0428 0.3386 0.0479 0.201 Uiso 1 1 calc R . .
H2C H -0.1048 0.2008 0.0195 0.201 Uiso 1 1 calc R . .
C3 C -0.6706(6) -0.4451(5) -0.4842(3) 0.0883(13) Uani 1 1 d . . .
H3A H -0.7083 -0.4592 -0.5347 0.106 Uiso 1 1 calc R . .
C4 C 0.1506(6) -0.1026(5) -0.3262(2) 0.0862(13) Uani 1 1 d . . .
H4A H 0.1923 -0.1223 -0.2819 0.103 Uiso 1 1 calc R . .
C5 C -0.5047(6) 0.1240(5) -0.4220(3) 0.0966(15) Uani 1 1 d . . .
H5A H -0.5664 0.1499 -0.4613 0.145 Uiso 1 1 calc R . .
H5B H -0.5596 0.0293 -0.4170 0.145 Uiso 1 1 calc R . .
H5C H -0.3999 0.1254 -0.4333 0.145 Uiso 1 1 calc R . .
C6 C 0.1310(6) -0.1881(5) -0.3986(3) 0.0958(15) Uani 1 1 d . . .
H6A H 0.1564 -0.2743 -0.4106 0.115 Uiso 1 1 calc R . .
C7 C 0.0704(6) -0.1214(6) -0.4444(3) 0.0925(14) Uani 1 1 d . . .
H7A H 0.0463 -0.1530 -0.4956 0.111 Uiso 1 1 calc R . .
C8 C 0.0395(5) 0.2350(6) -0.0540(2) 0.0956(15) Uani 1 1 d . . .
H8A H 0.1047 0.3178 -0.0685 0.115 Uiso 1 1 calc R . .
H8B H -0.0423 0.1790 -0.0965 0.115 Uiso 1 1 calc R . .
C9 C -0.7303(6) -0.5329(5) -0.4418(3) 0.0884(14) Uani 1 1 d . . .
H9A H -0.8154 -0.6169 -0.4565 0.106 Uiso 1 1 calc R . .
C10 C -0.4863(5) 0.2285(5) -0.3514(3) 0.0776(12) Uani 1 1 d . . .
H10A H -0.5931 0.2278 -0.3413 0.093 Uiso 1 1 calc R . .
H10B H -0.4338 0.3240 -0.3577 0.093 Uiso 1 1 calc R . .
C11 C 0.5708(5) 0.1265(5) 0.1541(2) 0.0839(13) Uani 1 1 d . . .
H11A H 0.5290 0.0773 0.1907 0.126 Uiso 1 1 calc R . .
H11B H 0.6303 0.2240 0.1772 0.126 Uiso 1 1 calc R . .
H11C H 0.6411 0.0788 0.1313 0.126 Uiso 1 1 calc R . .
C12 C -0.6391(5) -0.4736(4) -0.3701(2) 0.0718(11) Uani 1 1 d . . .
H12A H -0.6529 -0.5113 -0.3282 0.086 Uiso 1 1 calc R . .
C13 C 0.4327(5) 0.1256(4) 0.09584(19) 0.0623(9) Uani 1 1 d . . .
H13A H 0.3605 0.1732 0.1182 0.075 Uiso 1 1 calc R . .
H13B H 0.3717 0.0277 0.0720 0.075 Uiso 1 1 calc R . .
C14 C -0.1774(4) 0.2156(4) -0.29454(19) 0.0552(9) Uani 1 1 d . . .
C15 C -0.5286(4) -0.3527(4) -0.37321(19) 0.0555(9) Uani 1 1 d . . .
C16 C 0.1651(4) 0.1488(4) -0.20446(18) 0.0539(8) Uani 1 1 d . . .
H16A H 0.1288 0.0741 -0.1807 0.065 Uiso 1 1 calc R . .
C17 C -0.3146(4) -0.1243(3) -0.32713(19) 0.0547(8) Uani 1 1 d . . .
H17A H -0.3263 -0.1009 -0.3734 0.066 Uiso 1 1 calc R . .
C18 C -0.1945(4) -0.0224(4) -0.2654(2) 0.0566(9) Uani 1 1 d . . .
C19 C 0.3584(4) 0.2160(3) -0.03666(17) 0.0492(8) Uani 1 1 d . . .
C20 C 0.4971(4) 0.4556(4) -0.16136(18) 0.0540(8) Uani 1 1 d . . .
C21 C 0.0988(4) 0.0097(4) -0.33387(18) 0.0559(9) Uani 1 1 d . . .
C22 C -0.1024(4) 0.1177(4) -0.28155(17) 0.0501(8) Uani 1 1 d . . .
C23 C 0.2878(4) 0.2571(3) -0.16734(17) 0.0484(8) Uani 1 1 d . . .
C24 C 0.5313(4) 0.3986(3) -0.09176(18) 0.0503(8) Uani 1 1 d . . .
C25 C 0.0779(4) 0.1346(4) -0.28187(17) 0.0515(8) Uani 1 1 d . . .
H25A H 0.1235 0.2225 -0.2990 0.062 Uiso 1 1 calc R . .
C26 C 0.3895(4) 0.2834(3) -0.09448(17) 0.0464(7) Uani 1 1 d . . .
C27 C -0.4063(4) -0.2482(3) -0.31838(19) 0.0528(8) Uani 1 1 d . . .
H27A H -0.3890 -0.2691 -0.2717 0.063 Uiso 1 1 calc R . .
C28 C -0.0042(12) 0.5581(11) -0.2035(5) 0.253(6) Uani 1 1 d . . .
H18A H -0.0271 0.6384 -0.1744 0.379 Uiso 1 1 calc R . .
H18B H 0.1053 0.5861 -0.2113 0.379 Uiso 1 1 calc R . .
H18C H -0.0185 0.4805 -0.1778 0.379 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'
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
C19 S1 C13 105.83(17) . . ?
C14 S2 C10 103.47(18) . . ?
C19 S3 C8 104.4(2) . . ?
C14 S4 C1 104.4(3) . . ?
C21 O1 C7 106.3(3) . . ?
C15 O2 C3 105.9(3) . . ?
C20 O6 C23 110.2(2) . . ?
C28 C1 S4 117.7(7) . . ?
C28 C1 H1A 107.9 . . ?
S4 C1 H1A 107.9 . . ?
C28 C1 H1B 107.9 . . ?
S4 C1 H1B 107.9 . . ?
H1A C1 H1B 107.2 . . ?
C8 C2 H2A 109.5 . . ?
C8 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C8 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C9 C3 O2 111.2(4) . . ?
C9 C3 H3A 124.4 . . ?
O2 C3 H3A 124.4 . . ?
C21 C4 C6 107.3(4) . . ?
C21 C4 H4A 126.4 . . ?
C6 C4 H4A 126.4 . . ?
C10 C5 H5A 109.5 . . ?
C10 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C10 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 106.3(4) . . ?
C7 C6 H6A 126.9 . . ?
C4 C6 H6A 126.9 . . ?
C6 C7 O1 110.7(4) . . ?
C6 C7 H7A 124.7 . . ?
O1 C7 H7A 124.7 . . ?
C2 C8 S3 110.7(4) . . ?
C2 C8 H8A 109.5 . . ?
S3 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
S3 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C3 C9 C12 106.2(4) . . ?
C3 C9 H9A 126.9 . . ?
C12 C9 H9A 126.9 . . ?
C5 C10 S2 114.8(3) . . ?
C5 C10 H10A 108.6 . . ?
S2 C10 H10A 108.6 . . ?
C5 C10 H10B 108.6 . . ?
S2 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C13 C11 H11A 109.5 . . ?
C13 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C13 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C12 C9 107.6(4) . . ?
C15 C12 H12A 126.2 . . ?
C9 C12 H12A 126.2 . . ?
C11 C13 S1 107.3(3) . . ?
C11 C13 H13A 110.3 . . ?
S1 C13 H13A 110.3 . . ?
C11 C13 H13B 110.3 . . ?
S1 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C22 C14 S2 117.6(3) . . ?
C22 C14 S4 122.5(3) . . ?
S2 C14 S4 119.8(2) . . ?
C12 C15 O2 109.1(3) . . ?
C12 C15 C27 132.6(4) . . ?
O2 C15 C27 118.3(3) . . ?
C23 C16 C25 126.0(3) . . ?
C23 C16 H16A 117.0 . . ?
C25 C16 H16A 117.0 . . ?
C27 C17 C18 121.8(3) . . ?
C27 C17 H17A 119.1 . . ?
C18 C17 H17A 119.1 . . ?
O3 C18 C17 122.2(3) . . ?
O3 C18 C22 120.9(3) . . ?
C17 C18 C22 116.8(3) . . ?
C26 C19 S1 118.4(2) . . ?
C26 C19 S3 124.4(2) . . ?
S1 C19 S3 117.25(19) . . ?
O5 C20 O6 122.0(3) . . ?
O5 C20 C24 129.6(3) . . ?
O6 C20 C24 108.4(3) . . ?
C4 C21 O1 109.4(3) . . ?
C4 C21 C25 135.1(3) . . ?
O1 C21 C25 115.4(3) . . ?
C14 C22 C18 120.5(3) . . ?
C14 C22 C25 124.7(3) . . ?
C18 C22 C25 114.8(3) . . ?
C16 C23 O6 119.1(3) . . ?
C16 C23 C26 132.5(3) . . ?
O6 C23 C26 108.1(3) . . ?
O4 C24 C26 132.1(3) . . ?
O4 C24 C20 122.7(3) . . ?
C26 C24 C20 105.1(3) . . ?
C21 C25 C16 111.1(3) . . ?
C21 C25 C22 110.3(3) . . ?
C16 C25 C22 109.8(3) . . ?
C21 C25 H25A 108.5 . . ?
C16 C25 H25A 108.5 . . ?
C22 C25 H25A 108.5 . . ?
C19 C26 C24 124.4(3) . . ?
C19 C26 C23 128.2(3) . . ?
C24 C26 C23 107.3(3) . . ?
C17 C27 C15 126.7(3) . . ?
C17 C27 H27A 116.7 . . ?
C15 C27 H27A 116.7 . . ?
C1 C28 H18A 109.5 . . ?
C1 C28 H18B 109.5 . . ?
H18A C28 H18B 109.5 . . ?
C1 C28 H18C 109.5 . . ?
H18A C28 H18C 109.5 . . ?
H18B C28 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 C19 1.720(3) . ?
S1 C13 1.811(3) . ?
S2 C14 1.769(3) . ?
S2 C10 1.799(4) . ?
S3 C19 1.733(3) . ?
S3 C8 1.824(5) . ?
S4 C14 1.771(4) . ?
S4 C1 1.776(6) . ?
O1 C21 1.358(4) . ?
O1 C7 1.369(5) . ?
O2 C15 1.370(4) . ?
O2 C3 1.360(5) . ?
O3 C18 1.218(4) . ?
O4 C24 1.213(4) . ?
O5 C20 1.192(4) . ?
O6 C20 1.363(4) . ?
O6 C23 1.417(4) . ?
C1 C28 1.324(10) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C8 1.451(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C9 1.324(6) . ?
C3 H3A 0.9300 . ?
C4 C21 1.319(5) . ?
C4 C6 1.426(6) . ?
C4 H4A 0.9300 . ?
C5 C10 1.489(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.300(6) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C12 1.405(6) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C13 1.509(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C15 1.341(5) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C22 1.333(5) . ?
C15 C27 1.426(5) . ?
C16 C23 1.315(4) . ?
C16 C25 1.506(4) . ?
C16 H16A 0.9300 . ?
C17 C27 1.326(4) . ?
C17 C18 1.475(5) . ?
C17 H17A 0.9300 . ?
C18 C22 1.509(5) . ?
C19 C26 1.380(4) . ?
C20 C24 1.523(5) . ?
C21 C25 1.496(5) . ?
C22 C25 1.536(4) . ?
C23 C26 1.464(4) . ?
C24 C26 1.435(4) . ?
C25 H25A 0.9800 . ?
C27 H27A 0.9300 . ?
C28 H18A 0.9600 . ?
C28 H18B 0.9600 . ?
C28 H18C 0.9600 . ?
