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_7248131
_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_formula_moiety         'C12 H18 O3'
_chemical_formula_sum            'C12 H18 O3'
_chemical_formula_weight         210.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 103.606(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.589(2)
_cell_length_b                   8.8658(11)
_cell_length_c                   8.1243(11)
_cell_measurement_reflns_used    5214
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.53
_cell_volume                     1161.3(3)
_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 0.978
_diffrn_measured_fraction_theta_max 0.972
_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  0.0418
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11487
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         2.526
_diffrn_source                   'microfocus Mo X-ray tube'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8594
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Stalke et al., 2015)

 Equivalent reflections defined by point group 2/m for scaling and error model
 Mean and maximum errors in direction cosine check function =   0.001   0.015
 Restraint esd for equal adjacent scale factors =  0.0060
 Maximum odd and even orders for spherical harmonics =   1   4
 wR2(int) =  0.1376 (selected reflections only, before parameter refinement)
 wR2(int) =  0.0546 (selected reflections only, after parameter refinement)

   12304 total and   2785 unique reflections assuming Friedel's law
 plus   1288 total and   800 unique reflections in fast scans
 Reflections rejected for which |I-<I>|/su >   3.00
 where:  su^2 = sigma(I)^2 + (  0.04000 <I>)^2  (sigma(I) from SAINT)

   12112 total and   2783 unique reflections left after |I-<I>|/su test
 plus   1135 total and   745 unique reflections in fast scans
 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  15.9  0.0426  0.208 - 0.440  0.903 - 1.044  0.922  0.0405  24.7    4174    2820
   2  15.9  0.0386  0.145 - 0.233  0.937 - 1.044  0.884  0.0405  24.7    2491    1882
   3  15.9  0.0443  0.175 - 0.387  0.903 - 1.038  0.918  0.0405  24.7    4279    2994
   4  15.9  0.0415  0.108 - 0.208  0.924 - 1.023  1.011  0.0405  24.7    1168     830
   5f  0.0  0.1101  0.117 - 0.323  0.903 - 1.038  1.721  0.0405  24.7    1135     630

       3 Overloads replaced by fast scan measurements
   12115 Corrected reflections written to file hkl
 Estimated minimum and maximum transmission:  0.8594  1.0000
 Additional spherical absorption correction applied with mu*r =  0.0000
 3lambda correction factor = 0.00150
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2609
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0682P)^2^+0.6249P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2097
_reflns_number_total             2609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01196h1.cif
_cod_data_source_block           fayz002
_cod_depositor_comments
'Adding full bibliography for 7248131--7248132.cif.'
_cod_original_cell_volume        1161.4(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7248131
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              62783