Sustainable sorbitol-derived compounds for gelation of the full range of ethanol-water mixtures.
Dizon, Glenieliz C.; Atkinson, George; Argent, Stephen P.; Santu, Lea T.; Amabilino, David B.; Soft matter 16 (2020) 4640–4654; doi:10.1039/d0sm00343c

data_1557952
_publ_section_title
;
 Sustainable sorbitol-derived compounds for gelation of the full range of
 ethanol-water mixtures.
;
_journal_issue                   19
_journal_name_full               'Soft matter'
_journal_page_first              4640
_journal_page_last               4654
_journal_paper_doi               10.1039/d0sm00343c
_journal_volume                  16
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H20 O8'
_chemical_formula_sum            'C14 H20 O8'
_chemical_formula_weight         316.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-08-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-06 deposited with the CCDC.	2020-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.9088(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.92283(14)
_cell_length_b                   4.60123(7)
_cell_length_c                   17.4539(3)
_cell_measurement_reflns_used    7491
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.4150
_cell_measurement_theta_min      4.9530
_cell_volume                     715.66(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -50.00  34.00   1.00    6.00    --  -38.50  38.00 -60.00   84
  2  \w    -65.00  32.00   1.00    6.00    --  -38.50  57.00  60.00   97
  3  \w     20.00 115.00   1.00    6.00    --   42.83  38.00-120.00   95
  4  \w     11.00 117.00   1.00    6.00    --   42.83  77.00 120.00  106
  5  \w     33.00  98.00   1.00   24.00    --  104.50 -45.00  30.00   65
  6  \w     81.00 178.00   1.00   24.00    --  104.50  30.00 -90.00   97
  7  \w     59.00 178.00   1.00   24.00    --  104.50  15.00   0.00  119
  8  \w     77.00 175.00   1.00   24.00    --  104.50  61.00  90.00   98
  9  \w     33.00  98.00   1.00   24.00    --  104.50 -45.00 150.00   65
 10  \w     33.00  98.00   1.00   24.00    --  104.50 -45.00 -90.00   65
 11  \w     30.00  91.00   1.00   24.00    --  104.50 -30.00  90.00   61
 12  \w     23.00 109.00   1.00   24.00    --  104.50 -94.00  60.00   86
 13  \w     30.00  91.00   1.00   24.00    --  104.50 -30.00-180.00   61
 14  \w     30.00  91.00   1.00   24.00    --  104.50 -30.00 -30.00   61
 15  \w     23.00 109.00   1.00   24.00    --  104.50 -94.00  30.00   86
 16  \w     23.00 109.00   1.00   24.00    --  104.50 -94.00 -60.00   86
 17  \w     23.00 109.00   1.00   24.00    --  104.50 -94.00 150.00   86
 18  \w    -94.00  -2.00   1.00    6.00    --  -38.50 125.00  90.00   92
 19  \w     11.00 117.00   1.00    6.00    --   42.83  77.00-120.00  106
 20  \w     16.00 113.00   1.00    6.00    --   42.83  57.00  60.00   97
 21  \w     16.00 113.00   1.00    6.00    --   42.83  57.00-150.00   97
 22  \w     11.00 117.00   1.00    6.00    --   42.83  77.00 -30.00  106
 23  \w     73.00 178.00   1.00   24.00    --  104.50  77.00  30.00  105
 24  \w     81.00 178.00   1.00   24.00    --  104.50  30.00-180.00   97
 25  \w     77.00 102.00   1.00   24.00    --  104.50  61.00-150.00   25
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas S2'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1706627000
_diffrn_orient_matrix_UB_12      0.0418094000
_diffrn_orient_matrix_UB_13      0.0041163000
_diffrn_orient_matrix_UB_21      0.0152040000
_diffrn_orient_matrix_UB_22      0.3158298000
_diffrn_orient_matrix_UB_23      -0.0279232000
_diffrn_orient_matrix_UB_31      -0.0228339000
_diffrn_orient_matrix_UB_32      -0.1031227000
_diffrn_orient_matrix_UB_33      -0.0837539000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9752
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.532
_diffrn_reflns_theta_min         4.963
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    1.035
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over 			a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       plank
_exptl_crystal_F_000             336
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1179 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2828
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0253
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+0.1508P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0665
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                2777
_reflns_number_total             2828
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sm00343c2.cif
_cod_data_source_block           MBS-Van
_cod_depositor_comments
'Adding full bibliography for 1557951--1557952.cif.'
_cod_database_code               1557952
_nottingham_internal_coll_name   OGPALB
_nottingham_internal_coll_number 17025
_nottingham_internal_coll_client GPA/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '6.00, 24.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pcxga2
_nottingham_internal_coll_date   15/05/2017
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 25/05/2017
_nottingham_internal_process_user pcxga2
_nottingham_internal_solution_date 25/05/2017
_nottingham_internal_solution_user pcxga2
_nottingham_internal_refinement_date 20/06/2019
_nottingham_internal_refinement_user pczspa
_nottingham_internal_validation_date 2019
_nottingham_internal_validation_user pczspa
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H20 O8'
_chemical_oxdiff_usercomment
'OGPALB #17025 GVB-1352 IN FOMBLIM ON A MICROMOUNT FOR GPA/DBA'
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.824
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O22-H22
 0.84 with sigma of 0.02
 O4-H4
 0.84 with sigma of 0.02
 O2-H2
 0.84 with sigma of 0.02
 O8-H8
 0.84 with sigma of 0.02
 O12-H12
 0.84 with sigma of 0.02
3. Restrained planarity
 C13, C14, C15, C19
 with sigma of 0.01
4.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C9(H9), C13(H13)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B)
4.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C15(H15)
4.d Fitted hexagon refined as free rotating group:
 C17(C18,C19,C14,C15,C16)
4.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
4.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              4628
_shelx_hkl_checksum              62799
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.782