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#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/40/4024044.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_4024044
loop_
_publ_author_name
'Indrajit Das'
'Tarun K. Pal'
'Cheravakkattu G. Suresh'
'Tanmaya Pathak'
_publ_contact_author_address
'Department of Chemistry, IIT, Kharagpur 721 302, India'
_publ_contact_author_email       tpathak@chem.iitkgp.ernet.in
_publ_contact_author_name        'Tanmaya Pathak'
_publ_section_title
;
 Diastereoselective C-C Bond Formation at C-5 of Vinyl Sulfone-Modified
 Hex-5-enofuranosyl Carbohydrates: Diversity-Oriented Synthesis of
 Branched-Chain Sugars and Beyond
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5523
_journal_page_last               5533
_journal_paper_doi               10.1021/jo062373+
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C28 H30 O11 S'
_chemical_formula_sum            'C28 H30 O11 S'
_chemical_formula_weight         574.58
_space_group_IT_number           146
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_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                120.00
_cell_formula_units_Z            9
_cell_length_a                   27.9054(14)
_cell_length_b                   27.9054(14)
_cell_length_c                   9.5055(5)
_cell_measurement_reflns_used    9245
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.25
_cell_measurement_theta_min      1.46
_cell_volume                     6410.4(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'ω 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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9245
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         1.46
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.519
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'SADABS  (Bruker-AXS, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2718
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.11(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4073
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0415
_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)+(0.0742P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                3635
_reflns_number_total             4073
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062373+si20061117_031806.cif
_cod_data_source_block           sep9
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               4024044
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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 0.45985(4) 0.72526(4) 0.89057(9) 0.0441(2) Uani 1 1 d . . .
O7 O 0.51975(9) 0.90708(9) 0.3990(2) 0.0429(6) Uani 1 1 d . . .
O9 O 0.44595(9) 0.81292(10) 0.2704(2) 0.0425(6) Uani 1 1 d . . .
O2 O 0.39603(9) 0.76224(9) 0.5276(2) 0.0438(6) Uani 1 1 d . . .
O10 O 0.50299(11) 0.86326(12) 0.0958(3) 0.0571(7) Uani 1 1 d . . .
O1 O 0.51305(10) 0.74520(10) 0.4357(3) 0.0486(6) Uani 1 1 d . . .
C2 C 0.43918(14) 0.74785(14) 0.5467(4) 0.0408(8) Uani 1 1 d . . .
H2 H 0.4239 0.7103 0.5840 0.049 Uiso 1 1 calc R . .
O11 O 0.39107(10) 0.83967(11) 0.5345(3) 0.0553(7) Uani 1 1 d . . .
C28 C 0.41773(14) 0.81757(15) 0.5487(4) 0.0401(8) Uani 1 1 d . . .
O6 O 0.47173(13) 0.90472(12) 0.7492(3) 0.0676(8) Uani 1 1 d . . .
C4 C 0.47872(13) 0.84187(14) 0.5881(3) 0.0350(7) Uani 1 1 d . . .
O5 O 0.55362(10) 0.91279(12) 0.7069(3) 0.0635(8) Uani 1 1 d . . .
O4 O 0.42514(11) 0.67481(10) 0.8169(3) 0.0566(7) Uani 1 1 d . . .
O3 O 0.44928(11) 0.72895(11) 1.0356(3) 0.0573(7) Uani 1 1 d . . .
C24 C 0.50000(16) 0.89069(14) 0.6895(4) 0.0415(8) Uani 1 1 d . . .
C3 C 0.47808(13) 0.79085(13) 0.6523(3) 0.0340(7) Uani 1 1 d . . .
H3 H 0.5150 0.7948 0.6469 0.041 Uiso 1 1 calc R . .
C26 C 0.45780(16) 0.84003(15) 0.1474(4) 0.0434(9) Uani 1 1 d . . .
C5 C 0.51460(13) 0.85704(13) 0.4543(3) 0.0354(8) Uani 1 1 d . . .
H5 H 0.5515 0.8640 0.4806 0.042 Uiso 1 1 calc R . .
C1 C 0.46776(15) 0.75399(14) 0.4060(4) 0.0414(8) Uani 1 1 d . . .
H1 H 0.4422 0.7259 0.3399 0.050 Uiso 1 1 calc R . .
C8 C 0.58430(17) 0.73604(17) 0.3177(4) 0.0528(10) Uani 1 1 d . . .
C15 C 0.52914(16) 0.74105(15) 0.8719(4) 0.0463(9) Uani 1 1 d . . .
C7 C 0.52386(16) 0.71666(15) 0.3264(4) 0.0514(9) Uani 1 1 d . . .
H7A H 0.5112 0.7231 0.2372 0.062 Uiso 1 1 calc R . .
H7B H 0.5036 0.6772 0.3450 0.062 Uiso 1 1 calc R . .
O8 O 0.60753(12) 0.93646(14) 0.3401(4) 0.0812(10) Uani 1 1 d . . .
C19 C 0.5969(2) 0.7278(2) 0.7572(6) 0.0740(14) Uani 1 1 d . . .
H19 H 0.6062 0.7099 0.6892 0.089 Uiso 1 1 calc R . .
C27 C 0.40684(17) 0.83665(19) 0.0863(5) 0.0616(11) Uani 1 1 d . . .
H27A H 0.4147 0.8522 -0.0067 0.092 Uiso 1 1 calc R . .
H27B H 0.3951 0.8570 0.1445 0.092 Uiso 1 1 calc R . .
H27C H 0.3780 0.7986 0.0817 0.092 Uiso 1 1 calc R . .
C25 C 0.5801(2) 0.9576(2) 0.8068(6) 0.0816(15) Uani 1 1 d . . .
H25A H 0.5795 0.9895 0.7714 0.122 Uiso 1 1 calc R . .
H25B H 0.6178 0.9665 0.8206 0.122 Uiso 1 1 calc R . .
H25C H 0.5607 0.9466 0.8949 0.122 Uiso 1 1 calc R . .
C22 C 0.56945(17) 0.94378(16) 0.3415(4) 0.0524(10) Uani 1 1 d . . .
C20 C 0.54298(19) 0.71423(18) 0.7718(5) 0.0623(12) Uani 1 1 d . . .
H20 H 0.5158 0.6872 0.7149 0.075 Uiso 1 1 calc R . .
C6 C 0.49085(14) 0.81153(14) 0.3422(4) 0.0394(8) Uani 1 1 d . . .
H6 H 0.5199 0.8180 0.2742 0.047 Uiso 1 1 calc R . .
C16 C 0.56934(17) 0.78144(18) 0.9558(4) 0.0599(11) Uani 1 1 d . . .
H16 H 0.5601 0.7999 1.0226 0.072 Uiso 1 1 calc R . .
C14 C 0.45729(14) 0.78039(14) 0.8042(4) 0.0402(8) Uani 1 1 d . . .
H14A H 0.4193 0.7727 0.8048 0.048 Uiso 1 1 calc R . .
H14B H 0.4792 0.8140 0.8579 0.048 Uiso 1 1 calc R . .
C23 C 0.5675(2) 0.99251(19) 0.2846(6) 0.0806(15) Uani 1 1 d . . .
H23A H 0.5987 1.0259 0.3194 0.121 Uiso 1 1 calc R . .
H23B H 0.5339 0.9910 0.3141 0.121 Uiso 1 1 calc R . .
H23C H 0.5689 0.9921 0.1837 0.121 Uiso 1 1 calc R . .
C17 C 0.62346(19) 0.7939(2) 0.9389(6) 0.0735(13) Uani 1 1 d . . .
H17 H 0.6507 0.8210 0.9955 0.088 Uiso 1 1 calc R . .
C9 C 0.6017(2) 0.7039(2) 0.2479(7) 0.0831(15) Uani 1 1 d . . .
H9 H 0.5754 0.6698 0.2114 0.100 Uiso 1 1 calc R . .
C18 C 0.6382(2) 0.7676(2) 0.8412(6) 0.0759(14) Uani 1 1 d . . .
C21 C 0.6979(2) 0.7816(3) 0.8261(8) 0.117(2) Uani 1 1 d . . .
H21A H 0.7184 0.8162 0.7771 0.176 Uiso 1 1 calc R . .
H21B H 0.6994 0.7529 0.7740 0.176 Uiso 1 1 calc R . .
H21C H 0.7137 0.7847 0.9177 0.176 Uiso 1 1 calc R . .
C13 C 0.6237(2) 0.7866(3) 0.3623(7) 0.108(2) Uani 1 1 d . . .
H13 H 0.6131 0.8093 0.4081 0.130 Uiso 1 1 calc R . .
C10 C 0.6572(3) 0.7213(3) 0.2312(8) 0.107(2) Uani 1 1 d . . .
H10 H 0.6679 0.6986 0.1858 0.128 Uiso 1 1 calc R . .
C11 C 0.6954(3) 0.7708(4) 0.2805(8) 0.121(2) Uani 1 1 d . . .
H11 H 0.7328 0.7817 0.2739 0.145 Uiso 1 1 calc R . .
C12 C 0.6797(3) 0.8055(3) 0.3410(9) 0.132(3) Uani 1 1 d . . .
H12 H 0.7061 0.8412 0.3673 0.158 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
O3 S1 O4 118.83(17) . . ?
O3 S1 C15 108.67(17) . . ?
O4 S1 C15 108.34(18) . . ?
O3 S1 C14 106.57(17) . . ?
O4 S1 C14 108.99(16) . . ?
C15 S1 C14 104.52(16) . . ?
C22 O7 C5 116.7(3) . . ?
C26 O9 C6 117.0(3) . . ?
C28 O2 C2 109.5(2) . . ?
C7 O1 C1 113.8(3) . . ?
O2 C2 C1 108.5(3) . . ?
O2 C2 C3 103.1(3) . . ?
C1 C2 C3 111.3(3) . . ?
O2 C2 H2 111.2 . . ?
C1 C2 H2 111.2 . . ?
C3 C2 H2 111.2 . . ?
O11 C28 O2 122.2(3) . . ?
O11 C28 C4 130.1(3) . . ?
O2 C28 C4 107.7(3) . . ?
C24 C4 C28 113.6(3) . . ?
C24 C4 C3 113.2(3) . . ?
C28 C4 C3 101.0(3) . . ?
C24 C4 C5 111.5(3) . . ?
C28 C4 C5 110.2(3) . . ?
C3 C4 C5 106.6(3) . . ?
C24 O5 C25 117.3(3) . . ?
O6 C24 O5 125.1(3) . . ?
O6 C24 C4 124.8(3) . . ?
O5 C24 C4 110.0(3) . . ?
C2 C3 C14 114.8(3) . . ?
C2 C3 C4 98.1(3) . . ?
C14 C3 C4 112.2(3) . . ?
C2 C3 H3 110.4 . . ?
C14 C3 H3 110.4 . . ?
C4 C3 H3 110.4 . . ?
O10 C26 O9 123.9(3) . . ?
O10 C26 C27 125.9(3) . . ?
O9 C26 C27 110.2(3) . . ?
O7 C5 C6 110.2(3) . . ?
O7 C5 C4 107.8(3) . . ?
C6 C5 C4 113.2(3) . . ?
O7 C5 H5 108.5 . . ?
C6 C5 H5 108.5 . . ?
C4 C5 H5 108.5 . . ?
O1 C1 C2 105.4(3) . . ?
O1 C1 C6 108.3(3) . . ?
C2 C1 C6 112.9(3) . . ?
O1 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
C6 C1 H1 110.0 . . ?
C13 C8 C9 117.5(4) . . ?
C13 C8 C7 122.8(4) . . ?
C9 C8 C7 119.3(4) . . ?
C16 C15 C20 120.6(4) . . ?
C16 C15 S1 119.2(3) . . ?
C20 C15 S1 120.2(3) . . ?
O1 C7 C8 110.7(3) . . ?
O1 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C20 C19 C18 121.6(5) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O8 C22 O7 122.9(4) . . ?
O8 C22 C23 127.0(4) . . ?
O7 C22 C23 110.2(4) . . ?
C19 C20 C15 119.3(4) . . ?
C19 C20 H20 120.4 . . ?
C15 C20 H20 120.4 . . ?
O9 C6 C1 107.5(3) . . ?
O9 C6 C5 109.1(3) . . ?
C1 C6 C5 112.1(3) . . ?
O9 C6 H6 109.4 . . ?
C1 C6 H6 109.4 . . ?
C5 C6 H6 109.4 . . ?
C15 C16 C17 118.7(4) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C3 C14 S1 115.2(2) . . ?
C3 C14 H14A 108.5 . . ?
S1 C14 H14A 108.5 . . ?
C3 C14 H14B 108.5 . . ?
S1 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C17 C16 122.0(5) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C10 C9 C8 121.5(5) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C17 C18 C19 117.9(5) . . ?
C17 C18 C21 120.8(5) . . ?
C19 C18 C21 121.3(5) . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 C13 C12 121.4(6) . . ?
C8 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.2(6) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 119.2(7) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
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 O3 1.424(3) . ?
S1 O4 1.431(3) . ?
S1 C15 1.764(4) . ?
S1 C14 1.777(4) . ?
O7 C22 1.360(4) . ?
O7 C5 1.430(4) . ?
O9 C26 1.342(4) . ?
O9 C6 1.444(4) . ?
O2 C28 1.362(4) . ?
O2 C2 1.458(4) . ?
O10 C26 1.197(4) . ?
O1 C7 1.430(4) . ?
O1 C1 1.431(4) . ?
C2 C1 1.522(5) . ?
C2 C3 1.524(5) . ?
C2 H2 0.9800 . ?
O11 C28 1.188(4) . ?
C28 C4 1.531(5) . ?
O6 C24 1.186(5) . ?
C4 C24 1.526(5) . ?
C4 C3 1.541(5) . ?
C4 C5 1.542(5) . ?
O5 C24 1.313(4) . ?
O5 C25 1.446(5) . ?
C3 C14 1.529(5) . ?
C3 H3 0.9800 . ?
C26 C27 1.495(6) . ?
C5 C6 1.531(5) . ?
C5 H5 0.9800 . ?
C1 C6 1.525(5) . ?
C1 H1 0.9800 . ?
C8 C13 1.352(7) . ?
C8 C9 1.384(6) . ?
C8 C7 1.494(6) . ?
C15 C16 1.379(6) . ?
C15 C20 1.380(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O8 C22 1.178(5) . ?
C19 C20 1.364(7) . ?
C19 C18 1.386(7) . ?
C19 H19 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C22 C23 1.489(6) . ?
C20 H20 0.9300 . ?
C6 H6 0.9800 . ?
C16 C17 1.379(6) . ?
C16 H16 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C17 C18 1.369(7) . ?
C17 H17 0.9300 . ?
C9 C10 1.381(8) . ?
C9 H9 0.9300 . ?
C18 C21 1.514(7) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C13 C12 1.393(8) . ?
C13 H13 0.9300 . ?
C10 C11 1.339(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(10) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20575124
