#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/03/7150383.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_7150383
loop_
_publ_author_name
'Ley, Steven V.'
'Dixon, Darren J.'
'Guy, Richard T.'
'Palomero, Maria A.'
'Polara, Alessandra'
'Rodriguez, Felix'
'Sheppard, Tom D.'
_publ_section_title
;
 Studies on the generation of enolate anions from butane-2,3-diacetal
 protected glycolic acid derivatives and subsequent highly
 diastereoselective coupling reactions with aldehydes and acid
 chlorides.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3618
_journal_page_last               3627
_journal_paper_doi               10.1039/b412790k
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C14 H16 O8 S'
_chemical_formula_sum            'C14 H16 O8 S'
_chemical_formula_weight         344.33
_chemical_name_systematic
;
?
;
_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                 100.877(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.4730(2)
_cell_length_b                   11.0206(4)
_cell_length_c                   12.9676(5)
_cell_measurement_reflns_used    5286
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     768.10(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6902
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.70
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.14(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3411
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w==1/[σ²(Fo²)+(0.0437P)²+0.0479P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                3043
_reflns_number_total             3411
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b412790k.txt
_cod_data_source_block           sl0323
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7150383
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 0.43645(10) 0.79864(5) 0.24697(4) 0.02235(14) Uani 1 1 d . . .
O1 O 0.6951(3) 1.10783(15) 0.33350(13) 0.0280(4) Uani 1 1 d . . .
O2 O 0.8291(3) 1.08513(13) 0.50640(11) 0.0232(3) Uani 1 1 d . . .
O3 O 1.0544(3) 0.84609(15) 0.48895(13) 0.0235(4) Uani 1 1 d D . .
H3 H 1.064(5) 0.7629(17) 0.4705(19) 0.028 Uiso 1 1 d D . .
O4 O 1.2871(3) 1.04758(17) 0.62423(13) 0.0330(4) Uani 1 1 d . . .
O5 O 1.1259(3) 0.92414(16) 0.73299(12) 0.0303(4) Uani 1 1 d . . .
O6 O 0.6731(3) 0.84586(14) 0.32878(12) 0.0224(3) Uani 1 1 d . . .
O7 O 0.2580(3) 0.75128(15) 0.30348(12) 0.0280(4) Uani 1 1 d . . .
O8 O 0.5438(3) 0.72334(16) 0.17796(13) 0.0316(4) Uani 1 1 d . . .
C1 C 0.7195(4) 1.0456(2) 0.40939(18) 0.0214(5) Uani 1 1 d . . .
C2 C 0.6402(4) 0.9143(2) 0.41962(16) 0.0198(5) Uani 1 1 d . . .
H2 H 0.4639 0.9098 0.4300 0.024 Uiso 1 1 calc R . .
C3 C 0.8199(4) 0.8690(2) 0.51725(17) 0.0197(5) Uani 1 1 d . . .
C4 C 0.8554(4) 0.9870(2) 0.58251(17) 0.0219(5) Uani 1 1 d . . .
H4 H 0.7277 0.9937 0.6281 0.026 Uiso 1 1 calc R . .
C5 C 1.1152(4) 0.9932(2) 0.64744(17) 0.0234(5) Uani 1 1 d . . .
C6 C 0.7242(4) 0.7633(2) 0.57163(18) 0.0261(5) Uani 1 1 d . . .
H6A H 0.7071 0.6922 0.5254 0.039 Uiso 1 1 calc R . .
H6B H 0.5617 0.7839 0.5882 0.039 Uiso 1 1 calc R . .
H6C H 0.8415 0.7449 0.6367 0.039 Uiso 1 1 calc R . .
C7 C 1.3710(5) 0.9080(3) 0.7974(2) 0.0376(6) Uani 1 1 d . . .
H7A H 1.3540 0.8805 0.8676 0.056 Uiso 1 1 calc R . .
H7B H 1.4609 0.9853 0.8031 0.056 Uiso 1 1 calc R . .
H7C H 1.4635 0.8473 0.7651 0.056 Uiso 1 1 calc R . .
C8 C 0.3203(4) 0.9315(2) 0.18035(17) 0.0214(5) Uani 1 1 d . . .
C9 C 0.1225(4) 0.9925(2) 0.20905(18) 0.0267(5) Uani 1 1 d . . .
H9 H 0.0452 0.9620 0.2635 0.032 Uiso 1 1 calc R . .
C10 C 0.0389(5) 1.0989(2) 0.1569(2) 0.0319(6) Uani 1 1 d . . .
H10 H -0.0957 1.1419 0.1766 0.038 Uiso 1 1 calc R . .
C11 C 0.1491(5) 1.1437(2) 0.07627(19) 0.0305(6) Uani 1 1 d . . .
C12 C 0.3480(5) 1.0809(2) 0.04940(19) 0.0318(6) Uani 1 1 d . . .
H12 H 0.4255 1.1111 -0.0050 0.038 Uiso 1 1 calc R . .
C13 C 0.4348(4) 0.9749(2) 0.10081(18) 0.0273(5) Uani 1 1 d . . .
H13 H 0.5708 0.9324 0.0819 0.033 Uiso 1 1 calc R . .
C14 C 0.0533(6) 1.2581(3) 0.0194(3) 0.0471(8) Uani 1 1 d . . .
H14A H 0.1256 1.2668 -0.0438 0.071 Uiso 1 1 calc R . .
H14B H 0.1001 1.3281 0.0655 0.071 Uiso 1 1 calc R . .
H14C H -0.1284 1.2540 -0.0006 0.071 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
O8 S1 O7 120.85(11) . . ?
O8 S1 O6 103.17(9) . . ?
O7 S1 O6 109.02(9) . . ?
O8 S1 C8 109.27(10) . . ?
O7 S1 C8 109.78(11) . . ?
O6 S1 C8 103.16(10) . . ?
C1 O2 C4 111.14(17) . . ?
C3 O3 H3 109.4(16) . . ?
C5 O5 C7 116.0(2) . . ?
C2 O6 S1 120.21(13) . . ?
O1 C1 O2 123.0(2) . . ?
O1 C1 C2 129.2(2) . . ?
O2 C1 C2 107.86(19) . . ?
O6 C2 C1 110.19(18) . . ?
O6 C2 C3 110.19(18) . . ?
C1 C2 C3 103.44(18) . . ?
O6 C2 H2 110.9 . . ?
C1 C2 H2 110.9 . . ?
C3 C2 H2 110.9 . . ?
O3 C3 C6 113.20(18) . . ?
O3 C3 C2 108.32(18) . . ?
C6 C3 C2 114.40(18) . . ?
O3 C3 C4 105.33(17) . . ?
C6 C3 C4 114.46(18) . . ?
C2 C3 C4 99.95(17) . . ?
O2 C4 C5 107.91(17) . . ?
O2 C4 C3 105.58(16) . . ?
C5 C4 C3 110.56(18) . . ?
O2 C4 H4 110.9 . . ?
C5 C4 H4 110.9 . . ?
C3 C4 H4 110.9 . . ?
O4 C5 O5 125.3(2) . . ?
O4 C5 C4 125.6(2) . . ?
O5 C5 C4 109.01(19) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 121.2(2) . . ?
C9 C8 S1 120.09(18) . . ?
C13 C8 S1 118.69(18) . . ?
C8 C9 C10 118.8(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C11 121.1(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 118.8(2) . . ?
C12 C11 C14 120.8(2) . . ?
C10 C11 C14 120.4(2) . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C8 119.1(2) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 O8 1.4258(17) . ?
S1 O7 1.4258(17) . ?
S1 O6 1.5984(16) . ?
S1 C8 1.757(2) . ?
O1 C1 1.186(3) . ?
O2 C1 1.359(3) . ?
O2 C4 1.453(3) . ?
O3 C3 1.423(3) . ?
O3 H3 0.951(17) . ?
O4 C5 1.201(3) . ?
O5 C5 1.337(3) . ?
O5 C7 1.451(3) . ?
O6 C2 1.439(2) . ?
C1 C2 1.524(3) . ?
C2 C3 1.533(3) . ?
C2 H2 1.0000 . ?
C3 C6 1.506(3) . ?
C3 C4 1.544(3) . ?
C4 C5 1.511(3) . ?
C4 H4 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.384(3) . ?
C8 C13 1.389(3) . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 C14 1.504(4) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O8 S1 O6 C2 -172.73(16) . . . . ?
O7 S1 O6 C2 -43.11(18) . . . . ?
C8 S1 O6 C2 73.52(17) . . . . ?
C4 O2 C1 O1 -174.5(2) . . . . ?
C4 O2 C1 C2 5.9(2) . . . . ?
S1 O6 C2 C1 -110.67(18) . . . . ?
S1 O6 C2 C3 135.81(16) . . . . ?
O1 C1 C2 O6 36.8(3) . . . . ?
O2 C1 C2 O6 -143.54(17) . . . . ?
O1 C1 C2 C3 154.6(2) . . . . ?
O2 C1 C2 C3 -25.8(2) . . . . ?
O6 C2 C3 O3 41.1(2) . . . . ?
C1 C2 C3 O3 -76.7(2) . . . . ?
O6 C2 C3 C6 -86.2(2) . . . . ?
C1 C2 C3 C6 156.03(19) . . . . ?
O6 C2 C3 C4 151.04(17) . . . . ?
C1 C2 C3 C4 33.3(2) . . . . ?
C1 O2 C4 C5 134.66(19) . . . . ?
C1 O2 C4 C3 16.4(2) . . . . ?
O3 C3 C4 O2 81.61(19) . . . . ?
C6 C3 C4 O2 -153.39(19) . . . . ?
C2 C3 C4 O2 -30.7(2) . . . . ?
O3 C3 C4 C5 -34.8(2) . . . . ?
C6 C3 C4 C5 90.2(2) . . . . ?
C2 C3 C4 C5 -147.12(18) . . . . ?
C7 O5 C5 O4 -4.8(3) . . . . ?
C7 O5 C5 C4 172.6(2) . . . . ?
O2 C4 C5 O4 -17.3(3) . . . . ?
C3 C4 C5 O4 97.7(3) . . . . ?
O2 C4 C5 O5 165.27(17) . . . . ?
C3 C4 C5 O5 -79.7(2) . . . . ?
O8 S1 C8 C9 152.12(18) . . . . ?
O7 S1 C8 C9 17.5(2) . . . . ?
O6 S1 C8 C9 -98.63(19) . . . . ?
O8 S1 C8 C13 -29.4(2) . . . . ?
O7 S1 C8 C13 -164.10(18) . . . . ?
O6 S1 C8 C13 79.81(19) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
S1 C8 C9 C10 178.31(18) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C9 C10 C11 C14 179.0(2) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C14 C11 C12 C13 -179.3(2) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
S1 C8 C13 C12 -178.63(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21188955
