An organocatalytic strategy for the stereoselective synthesis of C-galactosides with fluorine at the pseudoanomeric carbon.
Altiti, Ahmad S.; Bachan, S.; Alrowhani, W.; Mootoo, D. R.; Organic & biomolecular chemistry 13 (2015) 10328–10335; doi:10.1039/c5ob01471a

data_7154647
_publ_section_title
;
 An organocatalytic strategy for the stereoselective synthesis of
 C-galactosides with fluorine at the pseudoanomeric carbon.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10328
_journal_page_last               10335
_journal_paper_doi               10.1039/c5ob01471a
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_compound_source        N/A
_chemical_formula_moiety         'C37 H39 F O5'
_chemical_formula_sum            'C37 H39 F O5'
_chemical_formula_weight         582.72
_chemical_melting_point          370
_chemical_name_common            'Fluoroalkene 11'
_chemical_name_systematic
;
3-?-(2?, 3?, 4?, 6?-?-Tetra-?-O-?-benzyl-?-\a-?-D-?- galactopyranosyl)-?-3-?-R-?-fluoropropene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-14 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.749(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.036(5)
_cell_length_b                   10.533(5)
_cell_length_c                   12.239(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1546.3(12)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.9553
_diffrn_measured_fraction_theta_max 0.9553
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71095
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20929
_diffrn_reflns_theta_full        30.1483
_diffrn_reflns_theta_max         30.15
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.086
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.2515
_exptl_crystal_description       needle
_exptl_crystal_F_000             620.3383
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether/methanol'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.8790
_refine_diff_density_min         -0.8275
_refine_diff_density_rms         0.2200
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   10.68(10)
_refine_ls_d_res_high            0.7078
_refine_ls_d_res_low             12.1970
_refine_ls_goodness_of_fit_ref   0.9821
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    72
_refine_ls_number_parameters     387
_refine_ls_number_reflns         8725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9821
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0655
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1206P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1831
_reflns_Friedel_coverage         0.917
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              17
_reflns_limit_l_min              -17
_reflns_number_gt                6688
_reflns_number_total             8725
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5ob01471a2.cif
_cod_data_source_block           MK-15-003-LT
_cod_depositor_comments          'Adding full bibliography for 7154647.cif.'
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7154647
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C19(H19a,H19b), C27(H27a,H27b), C34(H34a,H34b), C36(H36a,H36b)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33),
  C38(H38), C39(H39), C40(H40), C41(H41), C42(H42)
2.d X=CH2 refined with riding coordinates:
 C9(H9a,H9b)
;
_olex2_submission_special_instructions 'No special instructions were received'