#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/19/2221924.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_2221924
loop_
_publ_author_name
'Kuś, Piotr'
'Rojkiewicz, Marcin'
'Zieba, Grzegorz'
'Witoszek, Monika'
'Jones, Peter G.'
_publ_section_title
;
 (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-carboxypropanoate
;
_journal_coeditor_code           BT2936
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1192
_journal_paper_doi               10.1107/S1600536809015190
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H16 O6'
_chemical_formula_moiety         'C10 H16 O6'
_chemical_formula_sum            'C10 H16 O6'
_chemical_formula_weight         232.23
_chemical_melting_point          333
_chemical_name_common
;
1-O-2,3-isopropylideneglycerol hemisuccinate
;
_chemical_name_systematic
;
2,2-Dimethyl-1,3-dioxolan-4-ylmethyl 3-carboxypropanoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 98.658(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.7650(12)
_cell_length_b                   5.7007(3)
_cell_length_c                   9.6964(7)
_cell_measurement_reflns_used    7029
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7012
_cell_measurement_theta_min      4.3041
_cell_volume                     1134.73(12)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur diffractometer with an Atlas (Nova) detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10581
_diffrn_reflns_theta_full        74.49
_diffrn_reflns_theta_max         74.49
_diffrn_reflns_theta_min         4.31
_exptl_absorpt_coefficient_mu    0.964
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0399P)²+1.0966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1253
_reflns_number_gt                2170
_reflns_number_total             2304
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2936.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221924
_cod_database_fobs_code          2221924
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.44071(7) -0.1502(2) 0.58989(15) 0.0287(3) Uani d . 1 . .
H H01 0.4643(14) -0.164(5) 0.533(3) 0.047(8) Uiso d . 1 . .
O O2 0.47778(6) 0.2189(2) 0.59298(14) 0.0278(3) Uani d . 1 . .
C C1 0.44377(9) 0.0675(3) 0.63543(19) 0.0243(4) Uani d . 1 . .
C C2 0.40364(9) 0.1107(3) 0.7496(2) 0.0265(4) Uani d . 1 . .
H H2A 0.4299 0.0701 0.8403 0.032 Uiso calc R 1 . .
H H2B 0.3653 0.0055 0.7356 0.032 Uiso calc R 1 . .
C C3 0.38031(9) 0.3632(3) 0.75537(19) 0.0258(4) Uani d . 1 . .
H H3A 0.3599 0.3849 0.8405 0.031 Uiso calc R 1 . .
H H3B 0.4183 0.4697 0.7620 0.031 Uiso calc R 1 . .
C C4 0.33223(9) 0.4289(3) 0.6303(2) 0.0258(4) Uani d . 1 . .
O O3 0.32078(7) 0.3156(3) 0.52376(14) 0.0340(4) Uani d . 1 . .
O O4 0.30257(6) 0.6315(2) 0.65113(14) 0.0295(3) Uani d . 1 A .
C C5 0.26115(10) 0.7325(4) 0.5323(2) 0.0339(5) Uani d D 1 . .
H H5A 0.2372 0.6073 0.4752 0.041 Uiso calc PR 0.893(8) A 1
H H5B 0.2877 0.8205 0.4731 0.041 Uiso calc PR 0.893(8) A 1
H H5C 0.2798 0.8886 0.5170 0.041 Uiso calc PR 0.107(8) A 2
H H5D 0.2675 0.6354 0.4508 0.041 Uiso calc PR 0.107(8) A 2
O O5 0.16891(7) 0.7592(3) 0.65090(18) 0.0426(4) Uani d D 1 . .
O O6 0.10733(7) 0.9607(3) 0.48082(18) 0.0453(4) Uani d D 1 . .
C C6 0.21452(11) 0.8932(4) 0.5879(3) 0.0318(7) Uani d PD 0.893(8) A 1
H H6 0.2385 1.0041 0.6573 0.038 Uiso calc PR 0.893(8) A 1
C C7 0.17233(11) 1.0302(5) 0.4709(3) 0.0459(6) Uani d D 1 A .
H H7A 0.1779 1.2014 0.4852 0.055 Uiso calc PR 0.893(8) A 1
H H7B 0.1839 0.9886 0.3786 0.055 Uiso calc PR 0.893(8) A 1
H H7C 0.1896 1.1553 0.5371 0.055 Uiso calc PR 0.107(8) A 2
H H7D 0.1801 1.0664 0.3749 0.055 Uiso calc PR 0.107(8) A 2
C C6' 0.1934(9) 0.766(4) 0.523(2) 0.069(10) Uiso d PD 0.107(8) A 2
H H6' 0.1699 0.6485 0.4572 0.083 Uiso calc PR 0.107(8) A 2
C C8 0.10751(10) 0.8735(4) 0.6185(2) 0.0388(5) Uani d . 1 A .
C C9 0.10142(14) 1.0693(5) 0.7197(3) 0.0568(7) Uani d . 1 . .
H H9A 0.1050 1.0054 0.8144 0.085 Uiso calc R 1 A .
H H9B 0.0590 1.1461 0.6952 0.085 Uiso calc R 1 . .
H H9C 0.1362 1.1841 0.7156 0.085 Uiso calc R 1 . .
C C10 0.05421(12) 0.6939(5) 0.6160(3) 0.0532(7) Uani d . 1 . .
H H10A 0.0609 0.5680 0.5508 0.080 Uiso calc R 1 A .
H H10B 0.0119 0.7686 0.5861 0.080 Uiso calc R 1 . .
H H10C 0.0552 0.6282 0.7097 0.080 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 0.0181 0.0091 '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 0.0492 0.0322 '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
O2 C1 O1 . . 123.58(17) ?
O2 C1 C2 . . 122.95(17) ?
O1 C1 C2 . . 113.42(16) ?
C1 C2 C3 . . 113.37(16) ?
C4 C3 C2 . . 112.54(16) ?
O3 C4 O4 . . 123.59(18) ?
O3 C4 C3 . . 125.36(18) ?
O4 C4 C3 . . 111.05(16) ?
C4 O4 C5 . . 117.01(16) ?
C6' C5 O4 . . 124.8(7) ?
O4 C5 C6 . . 107.25(17) ?
C6' O5 C8 . . 102.9(7) ?
C8 O5 C6 . . 106.90(17) ?
C7 O6 C8 . . 106.95(17) ?
O5 C6 C5 . . 109.58(19) ?
O5 C6 C7 . . 104.30(18) ?
C5 C6 C7 . . 112.0(2) ?
O6 C7 C6 . . 104.48(19) ?
O6 C7 C6' . . 86.3(7) ?
C5 C6' O5 . . 115.5(14) ?
C5 C6' C7 . . 111.3(13) ?
O5 C6' C7 . . 100.5(11) ?
O6 C8 O5 . . 104.06(17) ?
O6 C8 C9 . . 111.3(2) ?
O5 C8 C9 . . 110.8(2) ?
O6 C8 C10 . . 109.0(2) ?
O5 C8 C10 . . 108.9(2) ?
C9 C8 C10 . . 112.4(2) ?
C1 O1 H01 . . 109(2) ?
C1 C2 H2A . . 108.9 ?
C3 C2 H2A . . 108.9 ?
C1 C2 H2B . . 108.9 ?
C3 C2 H2B . . 108.9 ?
H2A C2 H2B . . 107.7 ?
C4 C3 H3A . . 109.1 ?
C2 C3 H3A . . 109.1 ?
C4 C3 H3B . . 109.1 ?
C2 C3 H3B . . 109.1 ?
H3A C3 H3B . . 107.8 ?
O4 C5 H5A . . 110.3 ?
C6 C5 H5A . . 110.3 ?
C6' C5 H5B . . 122.2 ?
O4 C5 H5B . . 110.3 ?
C6 C5 H5B . . 110.3 ?
H5A C5 H5B . . 108.5 ?
C6' C5 H5C . . 106.1 ?
O4 C5 H5C . . 106.1 ?
H5A C5 H5C . . 137.6 ?
C6' C5 H5D . . 106.1 ?
O4 C5 H5D . . 106.1 ?
H5C C5 H5D . . 106.3 ?
O5 C6 H6 . . 110.3 ?
C5 C6 H6 . . 110.3 ?
C7 C6 H6 . . 110.3 ?
O6 C7 H7A . . 110.9 ?
C6 C7 H7A . . 110.9 ?
O6 C7 H7B . . 110.9 ?
C6 C7 H7B . . 110.9 ?
H7A C7 H7B . . 108.9 ?
O6 C7 H7C . . 114.3 ?
C6 C7 H7C . . 77.1 ?
C6' C7 H7C . . 114.3 ?
O6 C7 H7D . . 114.3 ?
C6 C7 H7D . . 130.1 ?
C6' C7 H7D . . 114.3 ?
H7C C7 H7D . . 111.4 ?
C5 C6' H6' . . 109.7 ?
O5 C6' H6' . . 109.7 ?
C7 C6' H6' . . 109.7 ?
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 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 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 . 1.316(2) ?
O2 C1 . 1.225(2) ?
C1 C2 . 1.502(3) ?
C2 C3 . 1.523(3) ?
C3 C4 . 1.498(3) ?
C4 O3 . 1.211(2) ?
C4 O4 . 1.338(2) ?
O4 C5 . 1.449(2) ?
C5 C6' . 1.408(16) ?
C5 C6 . 1.492(3) ?
O5 C6' . 1.409(17) ?
O5 C8 . 1.424(3) ?
O5 C6 . 1.424(3) ?
O6 C7 . 1.424(3) ?
O6 C8 . 1.424(3) ?
C6 C7 . 1.537(3) ?
C7 C6' . 1.629(17) ?
C8 C9 . 1.505(3) ?
C8 C10 . 1.505(3) ?
O1 H01 . 0.80(3) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C5 H5C . 0.9900 ?
C5 H5D . 0.9900 ?
C6 H6 . 1.0000 ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C7 H7C . 0.9900 ?
C7 H7D . 0.9900 ?
C6' H6' . 1.0000 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 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
O1 H01 O2 3_656 0.80(3) 1.86(3) 2.6582(19) 175(3)
C3 H3A O3 4_566 0.99 2.36 3.211(2) 143.8
C2 H2B O4 1_545 0.99 2.57 3.489(2) 154.9
C7 H7B O5 4_575 0.99 2.60 3.506(3) 152.1
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
O2 C1 C2 C3 . . . . 30.0(3) ?
O1 C1 C2 C3 . . . . -152.49(16) ?
C1 C2 C3 C4 . . . . 67.0(2) ?
C2 C3 C4 O3 . . . . -12.7(3) ?
C2 C3 C4 O4 . . . . 167.00(15) ?
O3 C4 O4 C5 . . . . -8.3(3) ?
C3 C4 O4 C5 . . . . 172.00(16) ?
C4 O4 C5 C6' . . . . 116.4(12) ?
C4 O4 C5 C6 . . . . 157.92(17) ?
C6' O5 C6 C5 . . . . -51.5(9) ?
C8 O5 C6 C5 . . . . -142.17(19) ?
C6' O5 C6 C7 . . . . 68.5(9) ?
C8 O5 C6 C7 . . . . -22.1(2) ?
C6' C5 C6 O5 . . . . 53.2(10) ?
O4 C5 C6 O5 . . . . -70.5(2) ?
C6' C5 C6 C7 . . . . -62.0(10) ?
O4 C5 C6 C7 . . . . 174.27(18) ?
C8 O6 C7 C6 . . . . 21.4(3) ?
C8 O6 C7 C6' . . . . 54.2(8) ?
O5 C6 C7 O6 . . . . 0.5(3) ?
C5 C6 C7 O6 . . . . 118.9(2) ?
O5 C6 C7 C6' . . . . -62.8(9) ?
C5 C6 C7 C6' . . . . 55.6(9) ?
O4 C5 C6' O5 . . . . 18(2) ?
C6 C5 C6' O5 . . . . -57.7(14) ?
O4 C5 C6' C7 . . . . 131.5(8) ?
C6 C5 C6' C7 . . . . 56.1(12) ?
C8 O5 C6' C5 . . . . 160.9(13) ?
C6 O5 C6' C5 . . . . 59.9(15) ?
C8 O5 C6' C7 . . . . 41.0(13) ?
C6 O5 C6' C7 . . . . -60.0(10) ?
O6 C7 C6' C5 . . . . 179.6(14) ?
C6 C7 C6' C5 . . . . -60.5(13) ?
O6 C7 C6' O5 . . . . -57.5(11) ?
C6 C7 C6' O5 . . . . 62.4(11) ?
C7 O6 C8 O5 . . . . -35.5(2) ?
C7 O6 C8 C9 . . . . 83.9(2) ?
C7 O6 C8 C10 . . . . -151.6(2) ?
C6' O5 C8 O6 . . . . -7.5(11) ?
C6 O5 C8 O6 . . . . 35.9(2) ?
C6' O5 C8 C9 . . . . -127.2(11) ?
C6 O5 C8 C9 . . . . -83.9(2) ?
C6' O5 C8 C10 . . . . 108.6(11) ?
C6 O5 C8 C10 . . . . 152.0(2) ?
