#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/40/4024041.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_4024041
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 H34 O10 S'
_chemical_formula_sum            'C28 H34 O10 S'
_chemical_formula_weight         562.61
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 90.08
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.926
_cell_length_b                   13.267
_cell_length_c                   14.196
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      1.43
_cell_volume                     1492.6
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.854
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       'omega scan'
_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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2923
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.43
_diffrn_standards_interval_time  '60 sec'
_diffrn_standards_number         25
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.863
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.774
_refine_ls_shift/su_mean         0.105
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1541P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1689
_reflns_number_gt                2129
_reflns_number_total             2731
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062373+si20061117_031659.cif
_cod_data_source_block           dmmdb
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024041
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 0.65659(15) 0.37943(10) 0.36511(10) 0.0524(4) Uani 1 1 d . . .
O1 O 0.3075(5) 0.1678(3) 0.4478(2) 0.0499(9) Uani 1 1 d . . .
O8 O 0.0481(5) 0.2480(4) 0.6065(3) 0.0688(11) Uani 1 1 d . . .
O4 O 0.1650(5) 0.2655(3) 0.2167(3) 0.0512(9) Uani 1 1 d . . .
O5 O 0.7957(5) 0.4252(3) 0.4141(4) 0.0703(12) Uani 1 1 d . . .
O10 O 0.2353(5) 0.5174(3) 0.4732(3) 0.0659(11) Uani 1 1 d . . .
O3 O 0.2677(6) 0.0797(3) 0.2233(3) 0.0649(11) Uani 1 1 d . . .
O2 O 0.4018(5) 0.0334(3) 0.3661(3) 0.0646(11) Uani 1 1 d . . .
O7 O 0.3175(5) 0.2805(3) 0.6425(3) 0.0626(11) Uani 1 1 d . . .
O6 O 0.6893(5) 0.2927(3) 0.3127(3) 0.0705(12) Uani 1 1 d . . .
O9 O 0.1345(7) 0.4732(4) 0.6227(4) 0.0809(14) Uani 1 1 d . . .
C16 C 0.1850(6) 0.3545(4) 0.4985(4) 0.0450(11) Uani 1 1 d . . .
H16 H 0.0738 0.3423 0.4705 0.054 Uiso 1 1 calc R . .
C3 C 0.1539(6) 0.2185(4) 0.3081(3) 0.0416(11) Uani 1 1 d . . .
H3 H 0.0507 0.2397 0.3405 0.050 Uiso 1 1 calc R . .
C21 C 0.5011(6) 0.3589(4) 0.4595(4) 0.0466(12) Uani 1 1 d . . .
H21A H 0.5369 0.3026 0.4982 0.056 Uiso 1 1 calc R . .
H21B H 0.4961 0.4183 0.4993 0.056 Uiso 1 1 calc R . .
C1 C 0.2588(7) 0.0830(4) 0.3991(4) 0.0525(12) Uani 1 1 d . . .
H1 H 0.1908 0.0384 0.4389 0.063 Uiso 1 1 calc R . .
C5 C 0.3214(6) 0.3367(4) 0.4185(4) 0.0420(11) Uani 1 1 d . . .
H5 H 0.3005 0.3880 0.3702 0.050 Uiso 1 1 calc R . .
C4 C 0.3114(6) 0.2393(4) 0.3711(4) 0.0417(11) Uani 1 1 d . . .
H4 H 0.4140 0.2287 0.3340 0.050 Uiso 1 1 calc R . .
C2 C 0.1625(7) 0.1085(4) 0.3028(4) 0.0480(12) Uani 1 1 d . . .
H2 H 0.0504 0.0775 0.2999 0.058 Uiso 1 1 calc R . .
C22 C 0.5619(7) 0.4582(4) 0.2777(4) 0.0540(13) Uani 1 1 d . . .
C27 C 0.4907(9) 0.4257(5) 0.1903(5) 0.0683(17) Uani 1 1 d . . .
H27 H 0.4952 0.3572 0.1766 0.082 Uiso 1 1 calc R . .
C17 C 0.1966(7) 0.2893(4) 0.5903(4) 0.0489(12) Uani 1 1 d . . .
C19 C 0.1817(7) 0.4551(4) 0.5399(4) 0.0524(14) Uani 1 1 d . . .
C10 C 0.0378(8) 0.3143(5) 0.0639(4) 0.0648(16) Uani 1 1 d . . .
C9 C 0.0244(8) 0.2484(5) 0.1510(4) 0.0655(16) Uani 1 1 d . . .
H9A H -0.0813 0.2626 0.1828 0.079 Uiso 1 1 calc R . .
H9B H 0.0234 0.1782 0.1321 0.079 Uiso 1 1 calc R . .
C23 C 0.5549(9) 0.5548(4) 0.3016(5) 0.0667(17) Uani 1 1 d . . .
H23 H 0.5979 0.5799 0.3579 0.080 Uiso 1 1 calc R . .
C6 C 0.3850(9) 0.0131(5) 0.2616(5) 0.0710(18) Uani 1 1 d . . .
C26 C 0.4156(11) 0.4882(6) 0.1248(5) 0.084(2) Uani 1 1 d . . .
H26 H 0.3719 0.4634 0.0686 0.101 Uiso 1 1 calc R . .
C20 C 0.2444(10) 0.6160(5) 0.5071(7) 0.087(2) Uani 1 1 d . . .
H20A H 0.2844 0.6597 0.4580 0.130 Uiso 1 1 calc R . .
H20B H 0.3208 0.6186 0.5596 0.130 Uiso 1 1 calc R . .
H20C H 0.1345 0.6375 0.5269 0.130 Uiso 1 1 calc R . .
C25 C 0.4090(10) 0.5847(6) 0.1460(6) 0.0803(19) Uani 1 1 d . . .
C24 C 0.4775(11) 0.6142(6) 0.2347(6) 0.084(2) Uani 1 1 d . . .
H24 H 0.4688 0.6823 0.2493 0.101 Uiso 1 1 calc R . .
C18 C 0.0399(11) 0.1841(7) 0.6924(6) 0.096(3) Uani 1 1 d . . .
H18A H -0.0721 0.1575 0.6992 0.143 Uiso 1 1 calc R . .
H18B H 0.0675 0.2240 0.7467 0.143 Uiso 1 1 calc R . .
H18C H 0.1188 0.1296 0.6869 0.143 Uiso 1 1 calc R . .
C15 C 0.1436(12) 0.2917(8) -0.0144(6) 0.104(3) Uani 1 1 d . . .
H15 H 0.2075 0.2330 -0.0121 0.125 Uiso 1 1 calc R . .
C11 C -0.0538(12) 0.3951(8) 0.0578(9) 0.118(3) Uani 1 1 d . . .
H11 H -0.1278 0.4117 0.1061 0.142 Uiso 1 1 calc R . .
C13 C 0.0599(19) 0.4363(16) -0.0939(12) 0.151(7) Uani 1 1 d . . .
H13 H 0.0631 0.4803 -0.1449 0.181 Uiso 1 1 calc R . .
C28 C 0.3247(17) 0.6534(9) 0.0721(7) 0.132(4) Uani 1 1 d . . .
H28A H 0.3285 0.7220 0.0933 0.197 Uiso 1 1 calc R . .
H28B H 0.2093 0.6332 0.0635 0.197 Uiso 1 1 calc R . .
H28C H 0.3837 0.6477 0.0133 0.197 Uiso 1 1 calc R . .
C8 C 0.3176(17) -0.0873(6) 0.2504(9) 0.141(5) Uani 1 1 d . . .
H8A H 0.3954 -0.1353 0.2763 0.211 Uiso 1 1 calc R . .
H8B H 0.3009 -0.1010 0.1846 0.211 Uiso 1 1 calc R . .
H8C H 0.2116 -0.0921 0.2828 0.211 Uiso 1 1 calc R . .
C7 C 0.5495(13) 0.0296(11) 0.2115(7) 0.126(4) Uani 1 1 d . . .
H7A H 0.5864 0.0978 0.2212 0.189 Uiso 1 1 calc R . .
H7B H 0.5346 0.0176 0.1453 0.189 Uiso 1 1 calc R . .
H7C H 0.6327 -0.0160 0.2360 0.189 Uiso 1 1 calc R . .
C14 C 0.1574(19) 0.3541(12) -0.0965(7) 0.136(5) Uani 1 1 d . . .
H14 H 0.2278 0.3388 -0.1469 0.163 Uiso 1 1 calc R . .
C12 C -0.0412(19) 0.4583(12) -0.0225(16) 0.179(8) Uani 1 1 d . . .
H12 H -0.1057 0.5168 -0.0251 0.215 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
O6 S1 O5 117.6(3) . . ?
O6 S1 C22 101.0(3) . . ?
O5 S1 C22 114.2(3) . . ?
O6 S1 C21 113.0(3) . . ?
O5 S1 C21 103.0(2) . . ?
C22 S1 C21 108.1(2) . . ?
C1 O1 C4 99.5(3) . . ?
C17 O8 C18 114.8(5) . . ?
C3 O4 C9 117.2(4) . . ?
C19 O10 C20 110.8(6) . . ?
C6 O3 C2 104.3(4) . . ?
C1 O2 C6 110.0(4) . . ?
C19 C16 C17 99.8(4) . . ?
C19 C16 C5 115.9(4) . . ?
C17 C16 C5 118.3(4) . . ?
O4 C3 C2 112.4(4) . . ?
O4 C3 C4 113.0(4) . . ?
C2 C3 C4 99.7(4) . . ?
C5 C21 S1 111.5(3) . . ?
O1 C1 O2 109.1(4) . . ?
O1 C1 C2 112.9(4) . . ?
O2 C1 C2 101.6(4) . . ?
C4 C5 C21 112.7(4) . . ?
C4 C5 C16 115.1(4) . . ?
C21 C5 C16 109.1(4) . . ?
O1 C4 C5 103.6(4) . . ?
O1 C4 C3 107.3(4) . . ?
C5 C4 C3 117.6(4) . . ?
O3 C2 C3 109.2(4) . . ?
O3 C2 C1 109.5(4) . . ?
C3 C2 C1 100.8(4) . . ?
C23 C22 C27 119.8(6) . . ?
C23 C22 S1 113.9(5) . . ?
C27 C22 S1 126.3(5) . . ?
C26 C27 C22 125.0(6) . . ?
O7 C17 O8 123.8(5) . . ?
O7 C17 C16 127.3(5) . . ?
O8 C17 C16 108.8(5) . . ?
O9 C19 O10 130.0(5) . . ?
O9 C19 C16 123.9(6) . . ?
O10 C19 C16 106.1(5) . . ?
C11 C10 C15 116.8(8) . . ?
C11 C10 C9 119.4(8) . . ?
C15 C10 C9 123.8(7) . . ?
O4 C9 C10 112.0(5) . . ?
C22 C23 C24 113.2(6) . . ?
O3 C6 C8 107.2(6) . . ?
O3 C6 O2 109.1(5) . . ?
C8 C6 O2 107.7(8) . . ?
O3 C6 C7 107.6(7) . . ?
C8 C6 C7 113.8(9) . . ?
O2 C6 C7 111.3(6) . . ?
C25 C26 C27 116.6(7) . . ?
C26 C25 C24 116.9(7) . . ?
C26 C25 C28 115.9(8) . . ?
C24 C25 C28 127.1(7) . . ?
C23 C24 C25 128.4(7) . . ?
C10 C15 C14 123.9(12) . . ?
C10 C11 C12 120.2(12) . . ?
C14 C13 C12 123.4(13) . . ?
C13 C14 C15 113.8(12) . . ?
C13 C12 C11 121.9(14) . . ?
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 O6 1.395(4) . ?
S1 O5 1.437(4) . ?
S1 C22 1.787(6) . ?
S1 C21 1.842(5) . ?
O1 C1 1.375(7) . ?
O1 C4 1.444(6) . ?
O8 C17 1.319(7) . ?
O8 C18 1.487(9) . ?
O4 C3 1.442(6) . ?
O4 C9 1.470(7) . ?
O10 C19 1.328(7) . ?
O10 C20 1.395(7) . ?
O3 C6 1.392(7) . ?
O3 C2 1.454(7) . ?
O2 C1 1.392(7) . ?
O2 C6 1.514(8) . ?
O7 C17 1.216(7) . ?
O9 C19 1.257(7) . ?
C16 C19 1.459(8) . ?
C16 C17 1.566(8) . ?
C16 C5 1.586(7) . ?
C3 C2 1.464(7) . ?
C3 C4 1.559(7) . ?
C21 C5 1.565(7) . ?
C1 C2 1.601(8) . ?
C5 C4 1.459(7) . ?
C22 C23 1.328(8) . ?
C22 C27 1.428(9) . ?
C27 C26 1.381(10) . ?
C10 C11 1.298(12) . ?
C10 C15 1.425(11) . ?
C10 C9 1.517(8) . ?
C23 C24 1.376(10) . ?
C6 C8 1.444(12) . ?
C6 C7 1.502(13) . ?
C26 C25 1.316(11) . ?
C25 C24 1.426(11) . ?
C25 C28 1.541(12) . ?
C15 C14 1.434(16) . ?
C11 C12 1.418(18) . ?
C13 C14 1.34(2) . ?
C13 C12 1.33(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20574431
