#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/40/4024042.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_4024042
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         'C20 H28 O8 S'
_chemical_formula_sum            'C20 H28 O8 S'
_chemical_formula_weight         428.48
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   11.111
_cell_length_b                   13.059
_cell_length_c                   15.198
_cell_measurement_reflns_used    2213
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.06
_cell_volume                     2205.1
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2213
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.06
_diffrn_standards_interval_time  '60 sec'
_diffrn_standards_number         25
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.756
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.756
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.125
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1699P)²+0.6841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1842
_reflns_number_gt                1530
_reflns_number_total             2213
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062373+si20061117_031723.cif
_cod_data_source_block           pttp4
_cod_database_code               4024042
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.46392(16) 0.94619(13) 0.37543(11) 0.0675(5) Uani 1 1 d . . .
O3 O 0.4152(4) 0.4276(3) 0.4149(3) 0.0592(10) Uani 1 1 d . . .
O1 O 0.3285(4) 0.6187(3) 0.5380(2) 0.0545(10) Uani 1 1 d . . .
O2 O 0.3844(4) 0.4508(3) 0.5598(2) 0.0633(11) Uani 1 1 d . . .
O4 O 0.2648(4) 0.6630(3) 0.3533(3) 0.0675(12) Uani 1 1 d . . .
O7 O 0.2179(4) 0.8345(3) 0.5985(3) 0.0737(13) Uani 1 1 d . . .
O8 O 0.3392(5) 0.7805(4) 0.7060(3) 0.0766(13) Uani 1 1 d . . .
O6 O 0.5578(4) 0.9742(4) 0.3146(3) 0.0909(17) Uani 1 1 d . . .
O5 O 0.4455(6) 1.0081(3) 0.4525(3) 0.0927(17) Uani 1 1 d . . .
C7 C 0.4210(5) 0.3762(4) 0.4966(4) 0.0542(14) Uani 1 1 d . . .
C19 C 0.3291(5) 0.9326(4) 0.2264(3) 0.0554(14) Uani 1 1 d . . .
H19 H 0.4019 0.9320 0.1962 0.066 Uiso 1 1 calc R . .
C2 C 0.3222(5) 0.5015(4) 0.4200(3) 0.0493(13) Uani 1 1 d . . .
H2 H 0.2491 0.4783 0.3900 0.059 Uiso 1 1 calc R . .
C4 C 0.4084(5) 0.6554(4) 0.4703(4) 0.0486(13) Uani 1 1 d . . .
H4 H 0.4905 0.6318 0.4826 0.058 Uiso 1 1 calc R . .
C3 C 0.3634(5) 0.6059(4) 0.3864(4) 0.0509(13) Uani 1 1 d . . .
H3 H 0.4277 0.5993 0.3426 0.061 Uiso 1 1 calc R . .
C1 C 0.3011(5) 0.5166(4) 0.5186(4) 0.0506(14) Uani 1 1 d . . .
H1 H 0.2182 0.4997 0.5351 0.061 Uiso 1 1 calc R . .
C14 C 0.3267(5) 0.9392(4) 0.3174(4) 0.0544(14) Uani 1 1 d . . .
C13 C 0.4937(5) 0.8178(4) 0.4086(4) 0.0598(15) Uani 1 1 d . . .
H13A H 0.4944 0.7748 0.3566 0.072 Uiso 1 1 calc R . .
H13B H 0.5737 0.8152 0.4342 0.072 Uiso 1 1 calc R . .
C5 C 0.4041(5) 0.7721(4) 0.4751(3) 0.0510(13) Uani 1 1 d . . .
H5 H 0.3231 0.7940 0.4580 0.061 Uiso 1 1 calc R . .
C18 C 0.2213(6) 0.9269(4) 0.1812(4) 0.0584(15) Uani 1 1 d . . .
H18 H 0.2225 0.9227 0.1202 0.070 Uiso 1 1 calc R . .
C17 C 0.1118(6) 0.9272(5) 0.2244(4) 0.0617(16) Uani 1 1 d . . .
C11 C 0.3151(7) 0.8098(4) 0.6235(4) 0.0596(15) Uani 1 1 d . . .
C15 C 0.2176(6) 0.9426(5) 0.3617(4) 0.0671(17) Uani 1 1 d . . .
H15 H 0.2161 0.9492 0.4226 0.081 Uiso 1 1 calc R . .
C16 C 0.1128(6) 0.9362(5) 0.3156(4) 0.0679(18) Uani 1 1 d . . .
H16 H 0.0401 0.9380 0.3459 0.081 Uiso 1 1 calc R . .
C10 C 0.4273(6) 0.8101(5) 0.5692(4) 0.0624(16) Uani 1 1 d . . .
H10A H 0.4871 0.7666 0.5969 0.075 Uiso 1 1 calc R . .
H10B H 0.4594 0.8792 0.5669 0.075 Uiso 1 1 calc R . .
C9 C 0.3367(8) 0.2857(5) 0.4997(5) 0.086(2) Uani 1 1 d . . .
H9A H 0.3431 0.2527 0.5560 0.129 Uiso 1 1 calc R . .
H9B H 0.3580 0.2380 0.4542 0.129 Uiso 1 1 calc R . .
H9C H 0.2556 0.3086 0.4909 0.129 Uiso 1 1 calc R . .
C6 C 0.2402(9) 0.6461(6) 0.2634(4) 0.087(2) Uani 1 1 d . . .
H6A H 0.1722 0.6867 0.2460 0.131 Uiso 1 1 calc R . .
H6B H 0.2225 0.5750 0.2541 0.131 Uiso 1 1 calc R . .
H6C H 0.3090 0.6652 0.2289 0.131 Uiso 1 1 calc R . .
C20 C -0.0049(6) 0.9205(6) 0.1756(5) 0.089(2) Uani 1 1 d . . .
H20A H -0.0705 0.9213 0.2168 0.134 Uiso 1 1 calc R . .
H20B H -0.0072 0.8580 0.1423 0.134 Uiso 1 1 calc R . .
H20C H -0.0120 0.9778 0.1364 0.134 Uiso 1 1 calc R . .
C8 C 0.5495(7) 0.3474(7) 0.5146(6) 0.092(2) Uani 1 1 d . . .
H8A H 0.5546 0.3130 0.5703 0.138 Uiso 1 1 calc R . .
H8B H 0.5982 0.4081 0.5161 0.138 Uiso 1 1 calc R . .
H8C H 0.5779 0.3027 0.4690 0.138 Uiso 1 1 calc R . .
C12 C 0.2365(9) 0.7772(7) 0.7642(5) 0.098(3) Uani 1 1 d . . .
H12A H 0.2620 0.7564 0.8218 0.147 Uiso 1 1 calc R . .
H12B H 0.1786 0.7291 0.7419 0.147 Uiso 1 1 calc R . .
H12C H 0.2005 0.8439 0.7674 0.147 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 118.9(3) . . ?
O6 S1 C14 108.6(3) . . ?
O5 S1 C14 108.2(3) . . ?
O6 S1 C13 106.6(3) . . ?
O5 S1 C13 109.0(3) . . ?
C14 S1 C13 104.7(3) . . ?
C7 O3 C2 108.0(4) . . ?
C1 O1 C4 107.5(4) . . ?
C1 O2 C7 107.7(4) . . ?
C3 O4 C6 114.3(5) . . ?
C11 O8 C12 115.0(6) . . ?
O3 C7 O2 104.7(4) . . ?
O3 C7 C8 108.8(5) . . ?
O2 C7 C8 108.6(6) . . ?
O3 C7 C9 111.8(5) . . ?
O2 C7 C9 109.7(5) . . ?
C8 C7 C9 112.8(6) . . ?
C14 C19 C18 118.9(6) . . ?
O3 C2 C3 111.8(4) . . ?
O3 C2 C1 104.7(4) . . ?
C3 C2 C1 105.0(5) . . ?
O1 C4 C3 104.8(4) . . ?
O1 C4 C5 106.2(4) . . ?
C3 C4 C5 117.1(5) . . ?
O4 C3 C4 109.2(4) . . ?
O4 C3 C2 110.9(5) . . ?
C4 C3 C2 101.4(4) . . ?
O1 C1 O2 110.2(5) . . ?
O1 C1 C2 107.2(4) . . ?
O2 C1 C2 104.8(4) . . ?
C15 C14 C19 120.1(6) . . ?
C15 C14 S1 120.8(4) . . ?
C19 C14 S1 119.1(5) . . ?
C5 C13 S1 115.5(4) . . ?
C13 C5 C4 109.6(5) . . ?
C13 C5 C10 112.2(5) . . ?
C4 C5 C10 111.2(4) . . ?
C17 C18 C19 121.8(5) . . ?
C18 C17 C16 117.8(6) . . ?
C18 C17 C20 121.8(6) . . ?
C16 C17 C20 120.4(6) . . ?
O7 C11 O8 124.0(6) . . ?
O7 C11 C10 125.4(5) . . ?
O8 C11 C10 110.5(6) . . ?
C14 C15 C16 119.8(5) . . ?
C15 C16 C17 121.6(6) . . ?
C11 C10 C5 111.9(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 O6 1.441(5) . ?
S1 O5 1.437(5) . ?
S1 C14 1.763(6) . ?
S1 C13 1.782(6) . ?
O3 C7 1.413(7) . ?
O3 C2 1.416(6) . ?
O1 C1 1.398(7) . ?
O1 C4 1.441(6) . ?
O2 C1 1.410(7) . ?
O2 C7 1.427(7) . ?
O4 C3 1.417(7) . ?
O4 C6 1.411(7) . ?
O7 C11 1.189(8) . ?
O8 C11 1.338(7) . ?
O8 C12 1.445(9) . ?
C7 C8 1.502(9) . ?
C7 C9 1.509(8) . ?
C19 C14 1.387(8) . ?
C19 C18 1.382(8) . ?
C2 C3 1.525(8) . ?
C2 C1 1.530(7) . ?
C4 C3 1.515(8) . ?
C4 C5 1.527(8) . ?
C14 C15 1.387(8) . ?
C13 C5 1.539(8) . ?
C5 C10 1.536(8) . ?
C18 C17 1.382(8) . ?
C17 C16 1.391(9) . ?
C17 C20 1.497(10) . ?
C11 C10 1.495(9) . ?
C15 C16 1.361(9) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658827
