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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/81/7218172.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_7218172
loop_
_publ_author_name
'Thiyagarajan, Shanmugam'
'Wu, Jing'
'Knoop, Rutger J.'
'Haveren, Jacco van'
'Lutz, Martin'
'ES, Daan van'
_publ_section_title
;
 Isohexide hydroxy esters: synthesis and application of a new class of
 biobased AB-type building blocks
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA07896A
_journal_year                    2014
_chemical_absolute_configuration unkn
_chemical_formula_moiety         'C7 H10 O5'
_chemical_formula_sum            'C7 H10 O5'
_chemical_formula_weight         174.15
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.295(3)
_cell_angle_beta                 102.547(2)
_cell_angle_gamma                102.956(3)
_cell_formula_units_Z            1
_cell_length_a                   5.0392(2)
_cell_length_b                   5.4022(2)
_cell_length_c                   7.5864(3)
_cell_measurement_reflns_used    5543
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.82
_cell_volume                     191.601(14)
_computing_cell_refinement       Peakref
_computing_data_collection       Apex2
_computing_data_reduction        'Eval15, SADABS-2008/1'
_computing_structure_refinement  'SHELXT (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5668
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             92
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1706
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0247
_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)+(0.0434P)²+0.0291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0642
_refine_ls_wR_factor_ref         0.0646
_reflns_number_gt                1691
_reflns_number_total             1706
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c4ra07896a2.cif
_cod_data_source_block           l0384a
_cod_original_cell_volume        191.598(15)
_cod_database_code               7218172
loop_
_symmetry_equiv_pos_as_xyz
'x, y, 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
O1 O 0.73010(16) 0.38133(15) 0.69142(10) 0.01410(17) Uani 1 1 d .
O2 O 0.43457(17) 0.76730(15) 0.47073(11) 0.01768(19) Uani 1 1 d .
O3 O 0.87453(16) 0.95128(16) 0.76891(11) 0.01410(17) Uani 1 1 d .
H3O H 0.825(4) 1.066(4) 0.727(3) 0.029(5) Uiso 1 1 d .
O4 O 0.01648(17) 0.13645(18) 0.24132(12) 0.0225(2) Uani 1 1 d .
O5 O 0.30466(17) 0.17657(18) 0.05526(12) 0.0213(2) Uani 1 1 d .
H5O H 0.153(4) 0.099(4) -0.028(3) 0.038(5) Uiso 1 1 d .
C1 C 0.7442(3) 0.5519(2) 0.86229(15) 0.0169(2) Uani 1 1 d .
H1A H 0.9400 0.6140 0.9423 0.020 Uiso 1 1 calc R
H1B H 0.6206 0.4619 0.9307 0.020 Uiso 1 1 calc R
C2 C 0.6427(2) 0.7759(2) 0.80262(14) 0.0143(2) Uani 1 1 d .
H2 H 0.5636 0.8647 0.8969 0.017 Uiso 1 1 calc R
C3 C 0.4111(2) 0.6379(2) 0.61879(14) 0.0138(2) Uani 1 1 d .
H3 H 0.2186 0.6153 0.6395 0.017 Uiso 1 1 calc R
C4 C 0.4674(2) 0.3712(2) 0.56350(14) 0.0121(2) Uani 1 1 d .
H4 H 0.3090 0.2237 0.5663 0.015 Uiso 1 1 calc R
C5 C 0.5129(2) 0.3589(2) 0.37104(14) 0.0120(2) Uani 1 1 d .
H5 H 0.6713 0.2795 0.3596 0.014 Uiso 1 1 calc R
C6 C 0.5975(2) 0.6490(2) 0.36611(15) 0.0171(2) Uani 1 1 d .
H6A H 0.8022 0.7266 0.4232 0.020 Uiso 1 1 calc R
H6B H 0.5522 0.6719 0.2371 0.020 Uiso 1 1 calc R
C7 C 0.2492(2) 0.2124(2) 0.21981(14) 0.0126(2) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0179(4) 0.0119(4) 0.0099(3) 0.0003(3) -0.0009(3) 0.0048(3)
O2 0.0230(4) 0.0124(4) 0.0149(4) 0.0018(3) -0.0017(3) 0.0067(3)
O3 0.0155(4) 0.0103(4) 0.0125(3) 0.0016(3) -0.0020(3) 0.0017(3)
O4 0.0126(4) 0.0321(5) 0.0171(4) -0.0026(3) 0.0037(3) 0.0008(3)
O5 0.0145(4) 0.0302(5) 0.0102(4) -0.0034(3) 0.0003(3) -0.0038(3)
C1 0.0242(5) 0.0142(5) 0.0092(5) 0.0014(4) 0.0022(4) 0.0020(4)
C2 0.0157(5) 0.0132(5) 0.0109(5) -0.0020(4) 0.0029(4) 0.0018(4)
C3 0.0124(5) 0.0137(5) 0.0131(5) -0.0006(4) 0.0020(4) 0.0032(4)
C4 0.0124(5) 0.0113(5) 0.0106(5) 0.0008(4) 0.0017(4) 0.0013(4)
C5 0.0113(4) 0.0123(5) 0.0103(4) -0.0001(4) 0.0017(4) 0.0021(4)
C6 0.0204(5) 0.0143(6) 0.0119(5) 0.0012(4) 0.0020(4) -0.0009(4)
C7 0.0132(5) 0.0106(5) 0.0118(5) -0.0005(4) 0.0013(4) 0.0031(4)
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
C1 O1 C4 106.28(8)
C3 O2 C6 107.70(8)
C2 O3 H3O 111.0(14)
C7 O5 H5O 109.4(13)
O1 C1 C2 104.44(9)
O1 C1 H1A 110.9
C2 C1 H1A 110.9
O1 C1 H1B 110.9
C2 C1 H1B 110.9
H1A C1 H1B 108.9
O3 C2 C1 107.87(9)
O3 C2 C3 111.02(8)
C1 C2 C3 102.39(9)
O3 C2 H2 111.7
C1 C2 H2 111.7
C3 C2 H2 111.7
O2 C3 C4 107.01(8)
O2 C3 C2 113.37(9)
C4 C3 C2 104.56(8)
O2 C3 H3 110.6
C4 C3 H3 110.6
C2 C3 H3 110.6
O1 C4 C5 108.72(8)
O1 C4 C3 105.74(8)
C5 C4 C3 105.31(9)
O1 C4 H4 112.2
C5 C4 H4 112.2
C3 C4 H4 112.2
C7 C5 C4 112.56(9)
C7 C5 C6 111.21(8)
C4 C5 C6 101.86(9)
C7 C5 H5 110.3
C4 C5 H5 110.3
C6 C5 H5 110.3
O2 C6 C5 104.99(9)
O2 C6 H6A 110.7
C5 C6 H6A 110.7
O2 C6 H6B 110.7
C5 C6 H6B 110.7
H6A C6 H6B 108.8
O4 C7 O5 123.29(10)
O4 C7 C5 125.71(10)
O5 C7 C5 110.99(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4421(13)
O1 C4 1.4455(13)
O2 C3 1.4278(13)
O2 C6 1.4380(14)
O3 C2 1.4279(14)
O3 H3O 0.81(2)
O4 C7 1.2082(14)
O5 C7 1.3310(13)
O5 H5O 0.85(2)
C1 C2 1.5112(15)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.5588(14)
C2 H2 1.0000
C3 C4 1.5399(15)
C3 H3 1.0000
C4 C5 1.5198(14)
C4 H4 1.0000
C5 C7 1.5102(14)
C5 C6 1.5380(15)
C5 H5 1.0000
C6 H6A 0.9900
C6 H6B 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3O O1 0.81(2) 1.91(2) 2.6993(12) 165(2) 1_565
O5 H5O O3 0.85(2) 1.77(2) 2.6107(11) 169(2) 1_444
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
C4 O1 C1 C2 -42.26(10)
O1 C1 C2 O3 -81.68(10)
O1 C1 C2 C3 35.49(11)
C6 O2 C3 C4 -20.86(11)
C6 O2 C3 C2 93.88(10)
O3 C2 C3 O2 -17.96(12)
C1 C2 C3 O2 -132.86(9)
O3 C2 C3 C4 98.23(10)
C1 C2 C3 C4 -16.66(11)
C1 O1 C4 C5 143.30(9)
C1 O1 C4 C3 30.65(10)
O2 C3 C4 O1 112.99(9)
C2 C3 C4 O1 -7.55(10)
O2 C3 C4 C5 -2.02(11)
C2 C3 C4 C5 -122.56(9)
O1 C4 C5 C7 149.88(8)
C3 C4 C5 C7 -97.19(10)
O1 C4 C5 C6 -90.94(10)
C3 C4 C5 C6 21.99(11)
C3 O2 C6 C5 35.46(11)
C7 C5 C6 O2 85.11(10)
C4 C5 C6 O2 -35.03(10)
C4 C5 C7 O4 8.16(15)
C6 C5 C7 O4 -105.42(13)
C4 C5 C7 O5 -172.09(9)
C6 C5 C7 O5 74.33(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 78427035
