De Novo Synthesis of Aceric Acid and an Aceric Acid Building Block
Mattie S. M. Timmer; Bridget L. Stocker; Peter H. Seeberger; Journal of Organic Chemistry 71 (2006) 8294–8297; doi:10.1021/jo061607m

data_4022023
_publ_contact_author_name        'Seeberger, P.H.'
_publ_section_title
;
 De Novo Synthesis of Aceric Acid and an Aceric Acid Building Block
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8294
_journal_page_last               8297
_journal_paper_doi               10.1021/jo061607m
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C14 H20 O10, H2 O'
_chemical_formula_sum            'C14 H22 O11'
_chemical_formula_weight         366.32
_chemical_name_common            'Methyl aceric acid dimer'
_chemical_name_systematic
;        
Dimethyl (2S,3R,3aS,4aS,6S,7R,7aS,8aS)-3,7-dihydroxy-2,6-dimethyl-
hexahydro-1,4,5,8-tetraoxa-s-indacene-3,7-dicarboxylate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1422(3)
_cell_length_b                   11.0909(4)
_cell_length_c                   21.2039(7)
_cell_measurement_reflns_used    4419
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.66
_cell_volume                     1679.63(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Kappa CCD'
_computing_data_reduction        'Denzo + Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP (Johnson,1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et Al., 1997)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3137
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.66
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut fragment'
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method MeOH/H2O
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         1859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+0.0330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                1675
_reflns_number_total             1859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061607msi20060803_021700.cif
_cod_database_code               4022023