Solubility- and melting-based approaches to evaluate the inner-crystal enantiophobia and enantiophilia undergoing a structural change within a homologous series, exemplified by chiral glycerol ethers
Zakharychev, Dmitry V.; Fayzullin, Robert R.; CrystEngComm 26 (2024) 1571–1582; doi:10.1039/D3CE01196H

data_7248132
_publ_section_title
;
 Solubility- and melting-based approaches to evaluate the inner-crystal
 enantiophobia and enantiophilia undergoing a structural change within a
 homologous series, exemplified by chiral glycerol ethers
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1571
_journal_page_last               1582
_journal_paper_doi               10.1039/D3CE01196H
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C12 H18 O3'
_chemical_formula_sum            'C12 H18 O3'
_chemical_formula_weight         210.26
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-11-08 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   4.83470(10)
_cell_length_b                   20.8619(5)
_cell_length_c                   22.8684(6)
_cell_measurement_reflns_used    40004
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      32.51
_cell_measurement_theta_min      2.64
_cell_volume                     2306.53(9)
_computing_cell_refinement       'APEX4 v2021.10-0 (Bruker AXS)'
_computing_data_collection       'APEX4 v2021.10-0 (Bruker AXS)'
_computing_data_reduction        'APEX4 v2021.10-0 (Bruker AXS)'
_computing_molecular_graphics
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012);
PLATON (Spek, 2009); Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012);
PLATON (Spek, 2009); Olex2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      102(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            117718
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.032
_diffrn_reflns_theta_min         2.146
_diffrn_source                   'microfocus Mo X-ray tube'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9416
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Stalke et al., 2015)

 Equivalent reflections defined by point group 222 for scaling and error model
 Mean and maximum errors in direction cosine check function =   0.000   0.000
 Restraint esd for equal adjacent scale factors =  0.0110
 Maximum odd and even orders for spherical harmonics =   1   4
 wR2(int) =  0.1670 (selected reflections only, before parameter refinement)
 wR2(int) =  0.0594 (selected reflections only, after parameter refinement)

  120704 total and   8448 unique reflections.
 Reflections rejected for which |I-<I>|/su >   3.00
 where:  su^2 = sigma(I)^2 + (  0.04000 <I>)^2  (sigma(I) from SAINT)

  119301 total and   8446 unique reflections left after |I-<I>|/su test
 su^2 = [K*sigma(I)]^2 + [g<I>]^2  where sigma(I) is from SAINT

 Error model 5: refine all K and overall g
 Run 2theta R(int) Incid. factors Diffr. factors    K      g   I/s(lim) Total I>2sig(I)
   1  22.0  0.0568  0.123 - 0.412  0.992 - 1.023  0.946  0.0249  40.1   14826   10212
   2  22.0  0.0504  0.330 - 0.414  0.998 - 1.036  0.895  0.0249  40.1   11728    8500
   3  21.9  0.0538  0.105 - 0.336  0.992 - 1.036  0.967  0.0249  40.1   14619   10104
   4  21.9  0.0504  0.063 - 0.313  0.992 - 1.036  0.978  0.0249  40.1   14428   10368
   5  21.9  0.0566  0.192 - 0.281  0.992 - 1.036  0.967  0.0249  40.1   14577   10543
   6  21.9  0.0538  0.074 - 0.342  0.992 - 1.036  0.971  0.0249  40.1   14404   10125
   7  21.9  0.0502  0.102 - 0.311  0.992 - 1.024  1.049  0.0249  40.1   11207    8564
   8   0.0  0.0464  0.180 - 0.318  0.992 - 1.033  1.010  0.0249  40.1   10816    8935
   9   0.0  0.0492  0.241 - 0.399  0.996 - 1.036  0.988  0.0249  40.1    8595    7011
  10   0.0  0.0764  0.266 - 0.307  0.993 - 1.017  1.017  0.0249  40.1    4101    3056

  119301 Corrected reflections written to file hkl
 Estimated minimum and maximum transmission:  0.9416  1.0000
 The ratio of these values is more reliable than their absolute values!
 3lambda correction factor = 0.00150
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       needle
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 2761 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_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     291
_refine_ls_number_reflns         8031
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0711P)^2^+0.3186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1206
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                7012
_reflns_number_total             8031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01196h1.cif
_cod_data_source_block           fayz003
_cod_depositor_comments
'Adding full bibliography for 7248131--7248132.cif.'
_cod_database_code               7248132
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              96961