Chemoenzymatic synthesis of carbasugars from iodobenzene.
Boyd, Derek R.; Sharma, Narain D.; Llamas, Nuria M.; Malone, John F.; O'Dowd, Colin R; Allen, Christopher C. R.; Organic & biomolecular chemistry 3 (2005) 1953–1963; doi:10.1039/b502009c

data_7150149
_publ_section_title
;
 Chemoenzymatic synthesis of carbasugars from iodobenzene.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1953
_journal_page_last               1963
_journal_paper_doi               10.1039/b502009c
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C16 H22 O10'
_chemical_formula_sum            'C16 H22 O10'
_chemical_formula_weight         374.34
_chemical_melting_point          139
_chemical_name_common
;Methyl(1R,2S,3R,4R,5S)-2,3,4,5-tetra(acetyloxy)cyclohexane-1-
carboxylate
;
_chemical_name_systematic
;
Methyl(1R,2S,3R,4R,5S)-2,3,4,5-tetra(acetyloxy)cyclohexane-1-carboxylate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.588(7)
_cell_angle_beta                 86.434(7)
_cell_angle_gamma                81.819(7)
_cell_formula_units_Z            2
_cell_length_a                   5.871(3)
_cell_length_b                   9.395(4)
_cell_length_c                   16.257(7)
_cell_measurement_reflns_used    662
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.90
_cell_measurement_theta_min      3.51
_cell_volume                     885.4(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97; enCIFer (CCDC, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker CCD area detector diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0092
_diffrn_reflns_av_sigmaI/netI    0.0876
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5440
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         1.26
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9736
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         4751
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0671
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1064P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1891
_reflns_number_gt                2995
_reflns_number_total             4751
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b502009c.txt
_cod_data_source_block           32
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7150149