A versatile approach toward enantiospecific synthesis of sugar-linked oxapolyquinanes <i>via</i> IPKR.
Maurya, Kanchan; Kaliappan, Krishna P.; Organic & biomolecular chemistry 23 (2025) 4409–4420; doi:10.1039/d4ob02016b

data_7160462
_publ_section_title
;
 A versatile approach toward enantiospecific synthesis of sugar-linked
 oxapolyquinanes <i>via</i> IPKR.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4409
_journal_page_last               4420
_journal_paper_doi               10.1039/d4ob02016b
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H16 O6'
_chemical_formula_sum            'C14 H16 O6'
_chemical_formula_weight         280.27
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-29
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2024-06-15 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2184(4)
_cell_length_b                   7.8161(5)
_cell_length_c                   22.5614(14)
_cell_measurement_reflns_used    3983
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.6780
_cell_measurement_theta_min      1.7800
_cell_volume                     1272.91(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    129.99 273.99   1.00    2.00   9.41 -12.98 -31.50    --   144
  2  \w   -108.63  15.37   1.00    2.00    --  -12.98 -59.25 122.08  124
  3  \w   -108.63  15.37   1.00    2.00    --  -12.98 -59.25  20.08  124
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0617024000
_diffrn_orient_matrix_UB_12      0.0504344000
_diffrn_orient_matrix_UB_13      -0.0171400000
_diffrn_orient_matrix_UB_21      -0.0512159000
_diffrn_orient_matrix_UB_22      0.0744089000
_diffrn_orient_matrix_UB_23      0.0073916000
_diffrn_orient_matrix_UB_31      0.0567641000
_diffrn_orient_matrix_UB_32      0.0123930000
_diffrn_orient_matrix_UB_33      0.0253073000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1627
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12304
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.987
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_min         1.805
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.462
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 630 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.8(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0591
_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^)+(0.0974P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1682
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1910
_reflns_number_total             2252
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob02016b2.cif
_cod_data_source_block           kpk_197_km_202_pkr_5_autored
_cod_depositor_comments
'Adding full bibliography for 7160461--7160463.cif.'
_cod_database_code               7160462
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.977
_reflns_odcompleteness_completeness 88.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.69
_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.a Ternary CH refined with riding coordinates:
 C009(H009), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008)
2.d Idealised Me refined as rotating group:
 C00J(H00E,H00H,H00J), C00K(H00K,H00L,H00M)
2.e Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_shelx_res_checksum              91057
_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 1.420
_oxdiff_exptl_absorpt_empirical_full_min 0.582