#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/93/2239311.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2239311
loop_
_publ_author_name
'Rjabovs, Vitālijs'
'Mishnev, Anatoly'
'Kiselovs, Glebs'
'Turks, Māris'
_publ_section_title
;
 {(3aR,5S,6R,6aR)-5-[(R)-1,2-Dihydroxyethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}methyl
 methanesulfonate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o524
_journal_page_last               o525
_journal_paper_doi               10.1107/S1600536814007387
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H20 O8 S'
_chemical_formula_moiety         'C11 H20 O8 S'
_chemical_formula_sum            'C11 H20 O8 S'
_chemical_formula_weight         312.33
_chemical_name_systematic
'{(3aR,5S,6R,6aR)-5-[(R)-1,2-Dihydroxyethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}methyl methanesulfonate'
_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                 98.9130(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.57940(10)
_cell_length_b                   15.6118(3)
_cell_length_c                   8.0653(2)
_cell_measurement_reflns_used    7583
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     694.04(3)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Bruker, 2004)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_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  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5266
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.213
_refine_ls_abs_structure_details 'Flack (1983), 1528 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.064(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0319P)²+0.0938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0646
_reflns_number_gt                3005
_reflns_number_total             3185
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zp2012sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2239311
_cod_database_fobs_code          2239311
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C9 0.0490(4) 0.33494(13) -0.8352(2) 0.0407(4) Uani d . 1 1
H H9A 0.1797 0.3741 -0.8422 0.061 Uiso calc R 1 1
H H9B -0.0757 0.3429 -0.9302 0.061 Uiso calc R 1 1
H H9C 0.1083 0.2772 -0.8345 0.061 Uiso calc R 1 1
C C7 -0.0536(3) 0.35157(11) -0.6762(2) 0.0316(3) Uani d . 1 1
C C8 -0.2632(4) 0.29425(14) -0.6553(2) 0.0470(5) Uani d . 1 1
H H8A -0.2092 0.2358 -0.6465 0.071 Uiso calc R 1 1
H H8B -0.3882 0.3003 -0.7507 0.071 Uiso calc R 1 1
H H8C -0.3262 0.3100 -0.5554 0.071 Uiso calc R 1 1
S S1 0.60651(6) 0.22002(2) -0.20810(5) 0.02715(10) Uani d . 1 1
O O4 0.22882(19) 0.51605(8) 0.01079(13) 0.0303(2) Uani d . 1 1
H H41 0.3738 0.5199 0.0049 0.046 Uiso calc R 1 1
O O1 -0.0420(3) 0.52359(9) -0.43022(15) 0.0465(4) Uani d . 1 1
O O6 0.55516(19) 0.31615(7) -0.26299(14) 0.0278(2) Uani d . 1 1
O O3 0.1263(2) 0.34259(7) -0.53311(14) 0.0347(3) Uani d . 1 1
O O5 -0.27358(19) 0.51658(8) -0.01728(15) 0.0364(3) Uani d . 1 1
H H51 -0.1929 0.5014 0.0716 0.055 Uiso calc R 1 1
O O2 -0.1278(2) 0.44075(9) -0.67350(16) 0.0396(3) Uani d . 1 1
O O8 0.8446(2) 0.20376(8) -0.24301(17) 0.0427(3) Uani d . 1 1
O O7 0.5551(2) 0.20875(9) -0.04236(15) 0.0426(3) Uani d . 1 1
C C10 0.3456(3) 0.35774(10) -0.2075(2) 0.0284(3) Uani d . 1 1
H H10A 0.3819 0.3718 -0.0891 0.034 Uiso calc R 1 1
H H10B 0.2063 0.3198 -0.2244 0.034 Uiso calc R 1 1
C C3 0.2921(3) 0.43831(10) -0.31045(18) 0.0247(3) Uani d . 1 1
H H3 0.4270 0.4787 -0.2833 0.030 Uiso calc R 1 1
C C1 0.0500(3) 0.48807(11) -0.5677(2) 0.0329(4) Uani d . 1 1
H H1 0.1185 0.5329 -0.6313 0.039 Uiso calc R 1 1
C C6 -0.1460(3) 0.58175(10) -0.0923(2) 0.0335(4) Uani d . 1 1
H H6A -0.1128 0.6293 -0.0147 0.040 Uiso calc R 1 1
H H6B -0.2477 0.6028 -0.1925 0.040 Uiso calc R 1 1
C C4 0.0556(3) 0.48076(10) -0.2760(2) 0.0276(3) Uani d . 1 1
H H4 -0.0583 0.4370 -0.2493 0.033 Uiso calc R 1 1
C C2 0.2447(3) 0.42291(10) -0.49929(19) 0.0277(3) Uani d . 1 1
H H2 0.3917 0.4282 -0.5511 0.033 Uiso calc R 1 1
C C5 0.0908(3) 0.54919(10) -0.13860(19) 0.0266(3) Uani d . 1 1
H H5 0.1789 0.5976 -0.1777 0.032 Uiso calc R 1 1
C C11 0.3976(3) 0.16137(13) -0.3475(3) 0.0445(4) Uani d . 1 1
H H11A 0.4188 0.1014 -0.3237 0.067 Uiso calc R 1 1
H H11B 0.4233 0.1724 -0.4605 0.067 Uiso calc R 1 1
H H11C 0.2358 0.1781 -0.3348 0.067 Uiso calc R 1 1
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
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O3 C7 O2 104.53(12)
O3 C7 C8 108.42(14)
O2 C7 C8 109.89(15)
O3 C7 C9 111.26(14)
O2 C7 C9 108.93(14)
C8 C7 C9 113.43(15)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O7 S1 O8 119.66(8)
O7 S1 O6 109.11(7)
O8 S1 O6 104.40(7)
O7 S1 C11 109.17(10)
O8 S1 C11 109.23(9)
O6 S1 C11 104.11(8)
C5 O4 H41 109.5
C1 O1 C4 111.21(12)
C10 O6 S1 117.00(10)
C7 O3 C2 108.57(12)
C6 O5 H51 109.5
C1 O2 C7 109.55(12)
O6 C10 C3 107.43(11)
O6 C10 H10A 110.2
C3 C10 H10A 110.2
O6 C10 H10B 110.2
C3 C10 H10B 110.2
H10A C10 H10B 108.5
C10 C3 C2 114.00(13)
C10 C3 C4 111.15(12)
C2 C3 C4 103.12(12)
C10 C3 H3 109.5
C2 C3 H3 109.5
C4 C3 H3 109.5
O1 C1 O2 112.02(14)
O1 C1 C2 107.70(13)
O2 C1 C2 105.27(13)
O1 C1 H1 110.6
O2 C1 H1 110.6
C2 C1 H1 110.6
O5 C6 C5 112.10(13)
O5 C6 H6A 109.2
C5 C6 H6A 109.2
O5 C6 H6B 109.2
C5 C6 H6B 109.2
H6A C6 H6B 107.9
O1 C4 C5 106.85(12)
O1 C4 C3 105.29(12)
C5 C4 C3 114.43(12)
O1 C4 H4 110.0
C5 C4 H4 110.0
C3 C4 H4 110.0
O3 C2 C3 109.51(12)
O3 C2 C1 103.57(12)
C3 C2 C1 105.03(12)
O3 C2 H2 112.7
C3 C2 H2 112.7
C1 C2 H2 112.7
O4 C5 C6 106.96(12)
O4 C5 C4 110.57(12)
C6 C5 C4 113.18(12)
O4 C5 H5 108.7
C6 C5 H5 108.7
C4 C5 H5 108.7
S1 C11 H11A 109.5
S1 C11 H11B 109.5
H11A C11 H11B 109.5
S1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 C7 1.506(2)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C7 O3 1.4140(19)
C7 O2 1.454(2)
C7 C8 1.503(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
S1 O7 1.4210(12)
S1 O8 1.4226(12)
S1 O6 1.5782(11)
S1 C11 1.7480(18)
O4 C5 1.4230(18)
O4 H41 0.8200
O1 C1 1.406(2)
O1 C4 1.442(2)
O6 C10 1.4669(17)
O3 C2 1.4238(19)
O5 C6 1.429(2)
O5 H51 0.8200
O2 C1 1.413(2)
C10 C3 1.511(2)
C10 H10A 0.9700
C10 H10B 0.9700
C3 C2 1.524(2)
C3 C4 1.540(2)
C3 H3 0.9800
C1 C2 1.528(2)
C1 H1 0.9800
C6 C5 1.515(2)
C6 H6A 0.9700
C6 H6B 0.9700
C4 C5 1.530(2)
C4 H4 0.9800
C2 H2 0.9800
C5 H5 0.9800
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H41 O5 1_655 0.82 2.00 2.820(2) 174 yes
O5 H51 O2 1_556 0.82 2.24 3.009(2) 156 yes
O5 H51 O4 . 0.82 2.49 2.777(2) 102 no
C3 H3 O5 1_655 0.98 2.58 3.344(2) 135 yes
C8 H8C O6 1_455 0.96 2.55 3.486(2) 165 yes
C9 H9A O4 1_554 0.96 2.55 3.306(2) 136 yes
C10 H10A O4 . 0.97 2.58 3.160(2) 118 no
C11 H11C O8 1_455 0.96 2.44 3.387(2) 167 yes
