#------------------------------------------------------------------------------
#$Date: 2021-02-05 11:09:52 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261789 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/02/1560280.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_1560280
loop_
_publ_author_name
'Aitken, R.'
'Haslett, Oliver'
'Slawin, Alexandra'
_publ_section_title
;
 (S)-1-(Ethoxycarbonyl)ethyl(2R,5S)-2,5-dimethyl-1,3-dioxolan-4-one-2-carboxylate
;
_journal_issue                   1
_journal_name_full               Molbank
_journal_page_first              M1178
_journal_paper_doi               10.3390/M1178
_journal_volume                  2021
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C11 H16 O7'
_chemical_formula_sum            'C11 H16 O7'
_chemical_formula_weight         260.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-06
_audit_creation_method           'by CrystalStructure 4.2'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   4.8832(7)
_cell_length_b                   7.5868(12)
_cell_length_c                   35.478(6)
_cell_measurement_reflns_used    3866
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.70
_cell_volume                     1314.4(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5175
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.300
_diffrn_reflns_theta_min         2.746
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552.00
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details
;
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0370P)²+0.1925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.593
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                2149
_reflns_number_total             2275
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            s5.cif
_cod_data_source_block           2
_cod_database_code               1560280
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0645(3) 0.2392(2) 0.33423(4) 0.0249(4) Uani 1 1 d . . . . .
O2 O 0.0348(3) 0.4873(2) 0.30010(5) 0.0339(4) Uani 1 1 d . . . . .
O4 O 0.4399(3) 0.1115(2) 0.30745(4) 0.0255(4) Uani 1 1 d . . . . .
O6 O 0.5518(3) 0.0518(2) 0.39519(4) 0.0285(4) Uani 1 1 d . . . . .
O7 O 0.4837(3) 0.3324(2) 0.37554(4) 0.0240(4) Uani 1 1 d . . . . .
O9 O 0.2363(3) 0.3340(2) 0.44226(5) 0.0321(4) Uani 1 1 d . . . . .
O10 O 0.5890(3) 0.4697(2) 0.47083(4) 0.0272(4) Uani 1 1 d . . . . .
C2 C 0.1554(5) 0.3546(3) 0.30779(7) 0.0256(5) Uani 1 1 d . . . . .
C3 C 0.4175(5) 0.2839(3) 0.29108(6) 0.0252(5) Uani 1 1 d . . . . .
H3 H 0.5759 0.3587 0.2991 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2708(4) 0.1063(3) 0.33981(6) 0.0232(5) Uani 1 1 d . . . . .
C6 C 0.4488(4) 0.1576(3) 0.37425(6) 0.0229(5) Uani 1 1 d . . . . .
C8 C 0.6455(4) 0.3995(3) 0.40661(6) 0.0244(5) Uani 1 1 d . . . . .
H8 H 0.8079 0.3215 0.4107 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4634(5) 0.3962(3) 0.44151(6) 0.0240(5) Uani 1 1 d . . . . .
C10 C 0.4344(5) 0.4668(3) 0.50611(6) 0.0290(5) Uani 1 1 d . . . . .
H10A H 0.4187 0.3445 0.5156 0.035 Uiso 1 1 calc R U . . .
H10B H 0.2476 0.5138 0.5020 0.035 Uiso 1 1 calc R U . . .
C11 C 0.5840(6) 0.5787(4) 0.53415(7) 0.0371(6) Uani 1 1 d . . . . .
H11A H 0.4841 0.5788 0.5581 0.045 Uiso 1 1 calc R U . . .
H11B H 0.7682 0.5308 0.5381 0.045 Uiso 1 1 calc R U . . .
H11C H 0.5978 0.6995 0.5246 0.045 Uiso 1 1 calc R U . . .
C12 C 0.4098(5) 0.2691(3) 0.24848(7) 0.0345(6) Uani 1 1 d . . . . .
H12A H 0.3945 0.3870 0.2374 0.041 Uiso 1 1 calc R U . . .
H12B H 0.5783 0.2127 0.2396 0.041 Uiso 1 1 calc R U . . .
H12C H 0.2516 0.1979 0.2409 0.041 Uiso 1 1 calc R U . . .
C13 C 0.1406(5) -0.0721(3) 0.34383(7) 0.0295(5) Uani 1 1 d . . . . .
H13A H 0.0243 -0.0736 0.3663 0.035 Uiso 1 1 calc R U . . .
H13B H 0.0289 -0.0971 0.3215 0.035 Uiso 1 1 calc R U . . .
H13C H 0.2837 -0.1620 0.3463 0.035 Uiso 1 1 calc R U . . .
C14 C 0.7405(6) 0.5820(3) 0.39599(7) 0.0332(6) Uani 1 1 d . . . . .
H14A H 0.8510 0.6312 0.4165 0.040 Uiso 1 1 calc R U . . .
H14B H 0.8513 0.5758 0.3730 0.040 Uiso 1 1 calc R U . . .
H14C H 0.5811 0.6577 0.3916 0.040 Uiso 1 1 calc R U . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(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
C2 O1 C5 108.51(17) . . ?
C5 O4 C3 108.02(16) . . ?
C6 O7 C8 116.33(17) . . ?
C9 O10 C10 115.14(18) . . ?
O2 C2 O1 122.6(2) . . ?
O2 C2 C3 128.8(2) . . ?
O1 C2 C3 108.6(2) . . ?
O4 C3 C2 103.27(18) . . ?
O4 C3 C12 109.73(19) . . ?
C2 C3 C12 113.4(2) . . ?
O4 C3 H3 110.1 . . ?
C2 C3 H3 110.1 . . ?
C12 C3 H3 110.1 . . ?
O4 C5 O1 106.12(17) . . ?
O4 C5 C13 110.45(18) . . ?
O1 C5 C13 110.36(17) . . ?
O4 C5 C6 107.80(16) . . ?
O1 C5 C6 108.99(17) . . ?
C13 C5 C6 112.87(19) . . ?
O6 C6 O7 125.9(2) . . ?
O6 C6 C5 123.6(2) . . ?
O7 C6 C5 110.31(18) . . ?
O7 C8 C14 107.46(18) . . ?
O7 C8 C9 107.11(17) . . ?
C14 C8 C9 113.41(19) . . ?
O7 C8 H8 109.6 . . ?
C14 C8 H8 109.6 . . ?
C9 C8 H8 109.6 . . ?
O9 C9 O10 124.8(2) . . ?
O9 C9 C8 124.1(2) . . ?
O10 C9 C8 111.04(18) . . ?
O10 C10 C11 107.9(2) . . ?
O10 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
O10 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 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
O1 C2 1.358(3) . ?
O1 C5 1.439(3) . ?
O2 C2 1.198(3) . ?
O4 C5 1.415(3) . ?
O4 C3 1.435(3) . ?
O6 C6 1.203(3) . ?
O7 C6 1.338(3) . ?
O7 C8 1.448(3) . ?
O9 C9 1.205(3) . ?
O10 C9 1.330(3) . ?
O10 C10 1.462(3) . ?
C2 C3 1.509(3) . ?
C3 C12 1.516(3) . ?
C3 H3 1.0000 . ?
C5 C13 1.502(3) . ?
C5 C6 1.549(3) . ?
C8 C14 1.508(3) . ?
C8 C9 1.525(3) . ?
C8 H8 1.0000 . ?
C10 C11 1.498(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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
C5 O1 C2 O2 -173.2(2) . . . . ?
C5 O1 C2 C3 7.7(2) . . . . ?
C5 O4 C3 C2 -19.1(2) . . . . ?
C5 O4 C3 C12 -140.23(19) . . . . ?
O2 C2 C3 O4 -172.2(2) . . . . ?
O1 C2 C3 O4 6.9(2) . . . . ?
O2 C2 C3 C12 -53.5(3) . . . . ?
O1 C2 C3 C12 125.6(2) . . . . ?
C3 O4 C5 O1 24.2(2) . . . . ?
C3 O4 C5 C13 143.83(19) . . . . ?
C3 O4 C5 C6 -92.4(2) . . . . ?
C2 O1 C5 O4 -19.7(2) . . . . ?
C2 O1 C5 C13 -139.3(2) . . . . ?
C2 O1 C5 C6 96.2(2) . . . . ?
C8 O7 C6 O6 -4.4(3) . . . . ?
C8 O7 C6 C5 179.62(16) . . . . ?
O4 C5 C6 O6 -97.7(2) . . . . ?
O1 C5 C6 O6 147.5(2) . . . . ?
C13 C5 C6 O6 24.5(3) . . . . ?
O4 C5 C6 O7 78.4(2) . . . . ?
O1 C5 C6 O7 -36.4(2) . . . . ?
C13 C5 C6 O7 -159.41(19) . . . . ?
C6 O7 C8 C14 160.84(19) . . . . ?
C6 O7 C8 C9 -77.0(2) . . . . ?
C10 O10 C9 O9 1.8(3) . . . . ?
C10 O10 C9 C8 -177.77(17) . . . . ?
O7 C8 C9 O9 5.6(3) . . . . ?
C14 C8 C9 O9 124.0(2) . . . . ?
O7 C8 C9 O10 -174.76(17) . . . . ?
C14 C8 C9 O10 -56.4(2) . . . . ?
C9 O10 C10 C11 -171.16(19) . . . . ?
