Yb(OTf)3-Catalyzed Desymmetrization of myo-Inositol 1,3,5-Orthoformate and Its Application in the Synthesis of Chiral Inositol Phosphates.
Padiyar, Laxmansingh T.; Zulueta, Medel Manuel L.; Sabbavarapu, Narayana Murthy; Hung, Shang-Cheng; The Journal of organic chemistry 82 (2017) 11418–11430; doi:10.1021/acs.joc.7b01919

data_4033012
_publ_section_title
;
 Yb(OTf)3-Catalyzed Desymmetrization of myo-Inositol 1,3,5-Orthoformate
 and Its Application in the Synthesis of Chiral Inositol Phosphates.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11418
_journal_page_last               11430
_journal_paper_doi               10.1021/acs.joc.7b01919
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H18 O9'
_chemical_formula_sum            'C17 H18 O9'
_chemical_formula_weight         366.31
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2012-11-01 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.341
_cell_length_b                   10.055
_cell_length_c                   21.981
_cell_measurement_reflns_used    4158
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3376
_cell_measurement_theta_min      2.9197
_cell_volume                     1622.500
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.4875
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.94
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0560077
_diffrn_orient_matrix_UB_12      -0.0383895
_diffrn_orient_matrix_UB_13      -0.0195699
_diffrn_orient_matrix_UB_21      -0.0678522
_diffrn_orient_matrix_UB_22      -0.00304
_diffrn_orient_matrix_UB_23      0.0229397
_diffrn_orient_matrix_UB_31      -0.0399215
_diffrn_orient_matrix_UB_32      0.0590769
_diffrn_orient_matrix_UB_33      -0.0115285
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17313
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         29.53
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.99844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.5
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(7)
_refine_ls_extinction_coef       0.0100(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0333P)^2^+0.3119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0766
_reflns_number_gt                3624
_reflns_number_total             4122
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01919_si_002.cif
_cod_data_source_block           i13181
_cod_depositor_comments          'Adding full bibliography for 4033012.cif.'
_cod_original_cell_volume        1622.5
_cod_database_code               4033012