Synthesis of [n,5]-Spiroketals by Ring Enlargement of Donor-Acceptor-Substituted Cyclopropane Derivatives
Christian Brand; Gesche Rauch; Michele Zanoni; Birger Dittrich; Daniel B. Werz; Journal of Organic Chemistry 74 (2009) 8779–8786; doi:10.1021/jo901902g

data_4025063
_publ_contact_author
;
Dittrich, Birger, Institute for inorganic chemistry,
Georg-August-University Goettingen, Tammannstr. 4,
D-37077 Goettingen, Germany.
;
_publ_contact_author_email       bdittri@gwdg.de
_publ_contact_author_fax         +49-551-3922582
_publ_contact_author_phone       +49-551-3919405
_publ_section_title
;
Synthesis of [n,5]-Spiroketals by Ring Enlargement of
Donor-Acceptor-Substituted Cyclopropane Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8779
_journal_page_last               8786
_journal_paper_doi               10.1021/jo901902g
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C22 H32 O8'
_chemical_formula_sum            'C22 H32 O8'
_chemical_formula_weight         424.48
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2009-09-01T18:51:09-00:00
_audit_creation_method           'XD routine XDCIF'
_cell_angle_alpha                90
_cell_angle_beta                 113.029(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2.0
_cell_length_a                   9.462(2)
_cell_length_b                   10.521(2)
_cell_length_c                   11.851(2)
_cell_measurement_reflns_used    5160
_cell_measurement_temperature    100
_cell_measurement_theta_max      53.98
_cell_measurement_theta_min      4.675
_cell_volume                     1085.8(4)
_computing_molecular_graphics    'Koritsanszky et al, (2003)'
_computing_publication_material  'Koritsanszky et al, (2003)'
_computing_structure_refinement  'Koritsanszky et al, (2003)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker Apex 2 Diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_UB_11      2.8039983e-02
_diffrn_orient_matrix_UB_12      9.1932677e-02
_diffrn_orient_matrix_UB_13      2.8682307e-03
_diffrn_orient_matrix_UB_21      -5.4426812e-02
_diffrn_orient_matrix_UB_22      5.3453292e-03
_diffrn_orient_matrix_UB_23      -9.1152497e-02
_diffrn_orient_matrix_UB_31      -9.7149141e-02
_diffrn_orient_matrix_UB_32      2.3539698e-02
_diffrn_orient_matrix_UB_33      9.4969776e-03
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            19371
_diffrn_reflns_theta_full        27.8
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         4.675
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6195
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS version 2008/2, Bruker AXS, 2008.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       plate
_exptl_crystal_F_000             456.0
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.0481
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         2175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
     calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0303
_reflns_number_gt                2175
_reflns_number_total             2845
_reflns_threshold_expression     F>3(\s)F
_cod_data_source_file            jo901902g_si_002_2.cif
_cod_data_source_block           glucose-6-alcohol
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025063