#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/77/2017741.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_2017741
loop_
_publ_author_name
'Lutz, Martin'
'van Krieken, Jan'
_publ_section_title
;
 (S,S)-Lactoyllactic acid and
 (S,S,S)-lactoyllactoyllactic acid
;
_journal_coeditor_code           BM3098
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o401
_journal_page_last               o405
_journal_paper_doi               10.1107/S0108270110026193
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H14 O7'
_chemical_formula_moiety         'C9 H14 O7'
_chemical_formula_sum            'C9 H14 O7'
_chemical_formula_weight         234.20
_chemical_name_systematic
;
(S,S,S)-3-Hydroxybut-3-en-2-yl
2-[(2-hydroxypropanoyl)oxy]propanoate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 123.8610(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.3594(5)
_cell_length_b                   5.62712(17)
_cell_length_c                   13.9888(6)
_cell_measurement_reflns_used    17211
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      1.75
_cell_volume                     1134.71(7)
_computing_cell_refinement       'PEAKREF (Schreurs, 2005)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction
;
EVAL15 (Schreurs et al.,  2010) and SADABS (Sheldrick,
2008a)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'manual editing of CIF from SHELXL97 (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008b)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0115
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19858
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1443
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0318P)²+0.5155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0685
_reflns_number_gt                1358
_reflns_number_total             1443
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm3098.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2017741
_cod_database_fobs_code          2017741
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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_disorder_assembly
_atom_site_disorder_group
O O1 0.17066(10) 0.4613(3) 0.73316(11) 0.0382(3) Uani d . 1 . .
O O2 0.11475(11) 0.7716(3) 0.61303(13) 0.0438(4) Uani d . 1 . .
H H2O 0.100(2) 0.823(8) 0.661(3) 0.085(10) Uiso d . 1 . .
O O3 0.25546(7) 0.2979(2) 0.62751(10) 0.0277(3) Uani d . 1 . .
O O4 0.35275(9) 0.6008(3) 0.72761(12) 0.0344(3) Uani d . 1 . .
O O5 0.49699(7) 0.2950(3) 0.85280(9) 0.0276(3) Uani d . 1 . .
O O6 0.50562(9) 0.3483(3) 0.70013(11) 0.0324(3) Uani d . 1 . .
O O7 0.68303(10) 0.5210(3) 0.84047(14) 0.0395(4) Uani d . 1 . .
H H7O 0.6698(19) 0.645(6) 0.803(2) 0.055(8) Uiso d . 1 . .
C C1 0.15700(12) 0.5649(3) 0.64948(15) 0.0275(4) Uani d . 1 . .
C C2 0.17984(11) 0.4664(4) 0.56672(14) 0.0258(4) Uani d . 1 . .
H H2 0.1973 0.5983 0.5344 0.031 Uiso calc R 1 . .
C C3 0.09807(12) 0.3285(4) 0.47044(15) 0.0339(4) Uani d . 1 . .
H H3A 0.0817 0.2000 0.5033 0.051 Uiso calc R 1 . .
H H3B 0.1148 0.2609 0.4197 0.051 Uiso calc R 1 . .
H H3C 0.0449 0.4354 0.4261 0.051 Uiso calc R 1 . .
C C4 0.33751(12) 0.3925(3) 0.70986(15) 0.0249(4) Uani d . 1 . .
C C5 0.40548(11) 0.1942(3) 0.77945(14) 0.0247(4) Uani d . 1 . .
H H5 0.4050 0.0729 0.7269 0.030 Uiso calc R 1 . .
C C6 0.38168(12) 0.0789(4) 0.85764(15) 0.0311(4) Uani d . 1 . .
H H6A 0.3839 0.1985 0.9100 0.047 Uiso calc R 1 . .
H H6B 0.4266 -0.0474 0.9025 0.047 Uiso calc R 1 . .
H H6C 0.3192 0.0108 0.8110 0.047 Uiso calc R 1 . .
C C7 0.53842(12) 0.3725(3) 0.80130(15) 0.0251(4) Uani d . 1 . .
C C8 0.63027(12) 0.4907(4) 0.88781(16) 0.0334(4) Uani d . 1 . .
H H8 0.6656 0.3837 0.9562 0.040 Uiso calc R 1 . .
C C9 0.61305(18) 0.7229(6) 0.9273(3) 0.0732(10) Uani d . 1 . .
H H9A 0.5828 0.8350 0.8628 0.110 Uiso calc R 1 . .
H H9B 0.6723 0.7893 0.9899 0.110 Uiso calc R 1 . .
H H9C 0.5729 0.6947 0.9549 0.110 Uiso calc R 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O2 H2O . . 109(3) ?
C4 O3 C2 . . 115.09(15) ?
C7 O5 C5 . . 116.91(13) ?
C8 O7 H7O . . 112.4(19) ?
O1 C1 O2 . . 124.60(17) ?
O1 C1 C2 . . 124.65(17) ?
O2 C1 C2 . . 110.61(15) ?
O3 C2 C3 . . 106.24(16) ?
O3 C2 C1 . . 109.06(13) ?
C3 C2 C1 . . 110.50(14) ?
O3 C2 H2 . . 110.3 ?
C3 C2 H2 . . 110.3 ?
C1 C2 H2 . . 110.3 ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O4 C4 O3 . . 124.84(18) ?
O4 C4 C5 . . 125.72(17) ?
O3 C4 C5 . . 109.38(15) ?
O5 C5 C6 . . 106.87(13) ?
O5 C5 C4 . . 108.75(15) ?
C6 C5 C4 . . 110.54(14) ?
O5 C5 H5 . . 110.2 ?
C6 C5 H5 . . 110.2 ?
C4 C5 H5 . . 110.2 ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
O6 C7 O5 . . 123.38(16) ?
O6 C7 C8 . . 125.91(15) ?
O5 C7 C8 . . 110.71(14) ?
O7 C8 C9 . . 112.3(2) ?
O7 C8 C7 . . 110.38(15) ?
C9 C8 C7 . . 109.68(16) ?
O7 C8 H8 . . 108.1 ?
C9 C8 H8 . . 108.1 ?
C7 C8 H8 . . 108.1 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.207(2) ?
O2 C1 . 1.317(2) ?
O2 H2O . 0.89(3) ?
O3 C4 . 1.346(2) ?
O3 C2 . 1.450(2) ?
O4 C4 . 1.197(2) ?
O5 C7 . 1.3430(19) ?
O5 C5 . 1.443(2) ?
O6 C7 . 1.203(2) ?
O7 C8 . 1.408(2) ?
O7 H7O . 0.83(3) ?
C1 C2 . 1.522(2) ?
C2 C3 . 1.517(2) ?
C2 H2 . 1.0000 ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C4 C5 . 1.518(3) ?
C5 C6 . 1.514(2) ?
C5 H5 . 1.0000 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 C8 . 1.516(3) ?
C8 C9 . 1.512(4) ?
C8 H8 . 1.0000 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
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
O2 H2O O6 3_455 0.89(3) 2.00(3) 2.7986(19) 149(3)
O2 H2O O7 3_455 0.89(3) 2.37(3) 3.049(2) 134(3)
O7 H7O O1 3 0.83(3) 2.03(3) 2.843(2) 166(3)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 O3 C2 C3 . . . . 173.83(14) y
C4 O3 C2 C1 . . . . -67.06(18) ?
O1 C1 C2 O3 . . . . -26.7(2) ?
O2 C1 C2 O3 . . . . 157.42(15) ?
O1 C1 C2 C3 . . . . 89.7(2) ?
O2 C1 C2 C3 . . . . -86.2(2) ?
C2 O3 C4 O4 . . . . -7.0(2) ?
C2 O3 C4 C5 . . . . 170.40(13) y
C7 O5 C5 C6 . . . . 169.37(16) ?
C7 O5 C5 C4 . . . . -71.28(18) y
O4 C4 C5 O5 . . . . -13.1(2) ?
O3 C4 C5 O5 . . . . 169.56(12) y
O4 C4 C5 C6 . . . . 103.9(2) ?
O3 C4 C5 C6 . . . . -73.41(17) ?
C5 O5 C7 O6 . . . . -4.7(3) ?
C5 O5 C7 C8 . . . . 175.50(16) y
O6 C7 C8 O7 . . . . -13.6(3) ?
O5 C7 C8 O7 . . . . 166.21(16) ?
O6 C7 C8 C9 . . . . 110.7(2) ?
O5 C7 C8 C9 . . . . -69.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654250
