Boronic acid-promoted site-selective Fischer esterifications of sugar alcohols
Manhas, Sanjay; Lin, Yu Chen; Wang, Grace; Kyne, Luke T.; Taylor, Mark S.; Green Chemistry 21 (2019) 5363–; doi:10.1039/C9GC00901A

data_7233731
_publ_section_title
;
 Boronic acid-promoted site-selective Fischer esterifications of sugar
 alcohols
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              5363
_journal_paper_doi               10.1039/C9GC00901A
_journal_volume                  21
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H30 O6'
_chemical_formula_sum            'C15 H30 O6'
_chemical_formula_weight         306.39
_chemical_melting_point          398.0(10)
_chemical_name_common            '(S,S,S)-arabitol monocaprate'
_chemical_name_systematic
'(2S,3S,4S)-2,3,4,5-tetrahydroxypentyl decanoate'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-03-15 deposited with the CCDC.    2019-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                81.706(2)
_cell_angle_beta                 89.469(3)
_cell_angle_gamma                86.953(3)
_cell_formula_units_Z            1
_cell_length_a                   4.8349(3)
_cell_length_b                   5.3640(3)
_cell_length_c                   16.1843(10)
_cell_measurement_reflns_used    9265
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.80
_cell_measurement_theta_min      2.76
_cell_volume                     414.75(4)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0448
_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       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10352
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        66.798
_diffrn_reflns_theta_max         66.797
_diffrn_reflns_theta_min         2.759
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.5307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       plate
_exptl_crystal_F_000             168
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 1285 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0502P)^2^+0.0440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0851
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_full    0.907
_reflns_Friedel_fraction_max     0.907
_reflns_number_gt                2767
_reflns_number_total             2808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc00901a2.cif
_cod_data_source_block           d1696_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '397--399' was changed to '398.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7233731.cif.
;
_cod_database_code               7233731
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.723
_shelx_estimated_absorpt_t_max   0.941
_shelx_res_checksum              65087