#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:04:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178419 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/40/4024043.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_4024043
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         'C17 H21 N O8 S'
_chemical_formula_sum            'C17 H21 N O8 S'
_chemical_formula_weight         399.42
_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                 90.36
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.843
_cell_length_b                   7.300
_cell_length_c                   11.813
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     935.0
_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  0.0074
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1882
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.72
_diffrn_standards_interval_time  '60 sec'
_diffrn_standards_number         25
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             418
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.19(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         1783
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.850
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          2.214
_refine_ls_shift/su_mean         0.268
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1713
_reflns_number_gt                1675
_reflns_number_total             1783
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062373+si20061117_031743.cif
_cod_data_source_block           44
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024043
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
C10 C 0.7994(4) 1.1878(6) 0.2952(3) 0.0382(9) Uani 1 1 d . . .
H10A H 0.8856 1.1992 0.3164 0.046 Uiso 1 1 calc R . .
H10B H 0.7824 1.2792 0.2375 0.046 Uiso 1 1 calc R . .
C13 C 0.5248(4) 0.9566(9) 0.2123(4) 0.0510(11) Uani 1 1 d . . .
H13 H 0.5231 0.9272 0.2889 0.061 Uiso 1 1 calc R . .
C11 C 0.6356(4) 0.9852(7) 0.1566(3) 0.0405(9) Uani 1 1 d . . .
C12 C 0.6386(5) 1.0261(8) 0.0437(4) 0.0492(11) Uani 1 1 d . . .
H12 H 0.7137 1.0471 0.0084 0.059 Uiso 1 1 calc R . .
C14 C 0.4166(4) 0.9735(10) 0.1492(4) 0.0555(11) Uani 1 1 d . . .
H14 H 0.3416 0.9588 0.1858 0.067 Uiso 1 1 calc R . .
O8 O 0.7576(4) 0.8376(5) 0.3241(3) 0.0521(9) Uani 1 1 d . . .
C15 C 0.4157(5) 1.0108(7) 0.0363(5) 0.0538(13) Uani 1 1 d . . .
C16 C 0.5297(5) 1.0362(8) -0.0183(4) 0.0559(13) Uani 1 1 d . . .
H16 H 0.5319 1.0598 -0.0956 0.067 Uiso 1 1 calc R . .
O7 O 0.8742(3) 0.9393(7) 0.1560(3) 0.0645(12) Uani 1 1 d . . .
C17 C 0.2970(6) 1.0208(11) -0.0317(6) 0.0742(18) Uani 1 1 d . . .
H17A H 0.3157 1.0476 -0.1093 0.111 Uiso 1 1 calc R . .
H17B H 0.2455 1.1157 -0.0016 0.111 Uiso 1 1 calc R . .
H17C H 0.2548 0.9055 -0.0273 0.111 Uiso 1 1 calc R . .
S1 S 0.77547(9) 0.96675(14) 0.23527(8) 0.0414(3) Uani 1 1 d . . .
O2 O 0.9859(3) 1.0006(7) 0.6752(3) 0.0573(11) Uani 1 1 d . . .
O1 O 0.8932(3) 1.0989(6) 0.5059(2) 0.0487(8) Uani 1 1 d . . .
C9 C 0.7215(3) 1.2297(6) 0.3978(3) 0.0361(9) Uani 1 1 d . . .
H9 H 0.6358 1.1950 0.3820 0.043 Uiso 1 1 calc R . .
O4 O 0.7696(4) 1.4520(5) 0.5368(3) 0.0625(11) Uani 1 1 d . . .
C5 C 0.9037(4) 0.9788(9) 0.7685(4) 0.0498(11) Uani 1 1 d . . .
C4 C 0.7646(4) 1.1363(6) 0.5078(3) 0.0365(9) Uani 1 1 d . . .
H4 H 0.7159 1.0269 0.5252 0.044 Uiso 1 1 calc R . .
O5 O 0.5503(4) 1.5098(8) 0.3217(4) 0.0774(14) Uani 1 1 d . . .
C3 C 0.7498(4) 1.2845(8) 0.5970(4) 0.0498(11) Uani 1 1 d . . .
H3 H 0.6697 1.2802 0.6348 0.060 Uiso 1 1 calc R . .
N1 N 0.5956(4) 1.5176(7) 0.4174(4) 0.0541(10) Uani 1 1 d . . .
C2 C 0.8588(4) 1.2547(8) 0.6787(4) 0.0509(12) Uani 1 1 d . . .
H2 H 0.8921 1.3700 0.7083 0.061 Uiso 1 1 calc R . .
C1 C 0.9529(4) 1.1492(8) 0.6078(4) 0.0468(10) Uani 1 1 d . . .
H1 H 1.0250 1.2259 0.5922 0.056 Uiso 1 1 calc R . .
C8 C 0.7265(4) 1.4357(6) 0.4297(4) 0.0454(11) Uani 1 1 d . . .
H8 H 0.7824 1.4993 0.3781 0.054 Uiso 1 1 calc R . .
O3 O 0.8235(4) 1.1336(8) 0.7650(3) 0.0694(13) Uani 1 1 d . . .
C6 C 0.8285(9) 0.8113(16) 0.7504(9) 0.103(3) Uani 1 1 d . . .
H6A H 0.8811 0.7055 0.7524 0.155 Uiso 1 1 calc R . .
H6B H 0.7879 0.8182 0.6781 0.155 Uiso 1 1 calc R . .
H6C H 0.7679 0.8018 0.8090 0.155 Uiso 1 1 calc R . .
O6 O 0.5492(5) 1.5904(10) 0.4963(4) 0.0935(19) Uani 1 1 d . . .
C7 C 0.9774(5) 0.9814(15) 0.8761(4) 0.074(2) Uani 1 1 d . . .
H7A H 1.0305 0.8763 0.8786 0.111 Uiso 1 1 calc R . .
H7B H 0.9226 0.9785 0.9396 0.111 Uiso 1 1 calc R . .
H7C H 1.0262 1.0910 0.8791 0.111 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'
N N 0.0061 0.0033 '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
C9 C10 S1 114.9(3) . . ?
C14 C13 C11 117.5(4) . . ?
C12 C11 C13 121.4(4) . . ?
C12 C11 S1 120.1(3) . . ?
C13 C11 S1 118.5(3) . . ?
C16 C12 C11 120.1(4) . . ?
C15 C14 C13 122.9(5) . . ?
C14 C15 C16 118.3(4) . . ?
C14 C15 C17 122.0(5) . . ?
C16 C15 C17 119.7(5) . . ?
C12 C16 C15 119.8(4) . . ?
O7 S1 O8 119.5(3) . . ?
O7 S1 C11 107.8(2) . . ?
O8 S1 C11 108.4(2) . . ?
O7 S1 C10 106.1(2) . . ?
O8 S1 C10 109.1(2) . . ?
C11 S1 C10 105.1(2) . . ?
C1 O2 C5 111.6(4) . . ?
C4 O1 C1 112.4(3) . . ?
C10 C9 C4 114.8(3) . . ?
C10 C9 C8 111.9(4) . . ?
C4 C9 C8 102.4(3) . . ?
C8 O4 C3 109.7(4) . . ?
O3 C5 O2 105.8(4) . . ?
O3 C5 C6 108.3(5) . . ?
O2 C5 C6 109.0(6) . . ?
O3 C5 C7 109.7(6) . . ?
O2 C5 C7 108.7(4) . . ?
C6 C5 C7 115.0(7) . . ?
O1 C4 C3 104.8(3) . . ?
O1 C4 C9 111.4(3) . . ?
C3 C4 C9 103.7(4) . . ?
O4 C3 C4 104.3(3) . . ?
O4 C3 C2 108.4(4) . . ?
C4 C3 C2 104.5(4) . . ?
O6 N1 O5 124.9(5) . . ?
O6 N1 C8 119.5(4) . . ?
O5 N1 C8 115.5(4) . . ?
O3 C2 C1 105.4(4) . . ?
O3 C2 C3 109.4(4) . . ?
C1 C2 C3 103.9(4) . . ?
O2 C1 O1 113.6(5) . . ?
O2 C1 C2 104.5(4) . . ?
O1 C1 C2 107.1(3) . . ?
O4 C8 C9 109.0(4) . . ?
O4 C8 N1 111.5(4) . . ?
C9 C8 N1 108.7(4) . . ?
C2 O3 C5 110.5(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
C10 C9 1.513(6) . ?
C10 S1 1.780(5) . ?
C13 C14 1.391(6) . ?
C13 C11 1.389(6) . ?
C11 C12 1.367(6) . ?
C11 S1 1.779(4) . ?
C12 C16 1.387(7) . ?
C14 C15 1.362(7) . ?
O8 S1 1.424(4) . ?
C15 C16 1.410(9) . ?
C15 C17 1.515(6) . ?
O7 S1 1.441(4) . ?
O2 C1 1.391(7) . ?
O2 C5 1.431(6) . ?
O1 C4 1.421(5) . ?
O1 C1 1.412(5) . ?
C9 C4 1.539(6) . ?
C9 C8 1.551(6) . ?
O4 C8 1.351(6) . ?
O4 C3 1.431(8) . ?
C5 O3 1.426(7) . ?
C5 C6 1.484(12) . ?
C5 C7 1.497(6) . ?
C4 C3 1.519(6) . ?
O5 N1 1.231(6) . ?
C3 C2 1.536(6) . ?
N1 O6 1.187(6) . ?
N1 C8 1.546(6) . ?
C2 O3 1.404(8) . ?
C2 C1 1.531(7) . ?
