Spacer-Mediated Synthesis of Contra-Thermodynamic Spiroacetals: Stereoselective Synthesis of C~2~-Symmetric Difructose Dianhydrides
Enrique M. Rubio; M. Isabel García-Moreno; Patricia Balbuena; Fernando J. Lahoz; Eleuterio Álvarez; Carmen Ortiz Mellet; José M. García Fernández; Journal of Organic Chemistry 71 (2006) 2257–2266; doi:10.1021/jo052184b

data_4021549
_publ_section_title
;
 Spacer-Mediated Synthesis of Contra-Thermodynamic Spiroacetals:
 Stereoselective Synthesis of C~2~-Symmetric Difructose Dianhydrides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2257
_journal_page_last               2266
_journal_paper_doi               10.1021/jo052184b
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C96 H100 O20'
_chemical_formula_sum            'C96 H100 O20'
_chemical_formula_weight         1573.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 95.554(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   59.445(3)
_cell_length_b                   10.5079(5)
_cell_length_c                   25.8107(11)
_cell_measurement_reflns_used    8638
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.59
_cell_measurement_theta_min      2.31
_cell_volume                     16046.8(13)
_computing_cell_refinement       'SAINT+ v. 7.06a (Bruker AXS, 2003)'
_computing_data_collection       'SMART v. 5.630 (Bruker AXS, 2003)'
_computing_data_reduction        'SAINT+ v. 7.06a (Bruker AXS, 2003)'
_computing_molecular_graphics    'XP program, SHELXTL v6.12, Bruker2000'
_computing_publication_material  'XCIF program, SHELXTLv6.12, BrukerAXS'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Giacovazzo, 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'BrukerAXS SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       '\w rotations with narrow frames'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_source         'Daresbury SRS Station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.69340
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_av_sigmaI/netI    0.1414
_diffrn_reflns_limit_h_max       75
_diffrn_reflns_limit_h_min       -78
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            78891
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        'no decay'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS: Area-Detector Absorption Correction. (1996)  Bruker-AXS 
 within SAINT+ package, v. 7.06.              
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             6688
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     2515
_refine_ls_number_reflns         20722
_refine_ls_number_restraints     3513
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0874
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1225P)^2^+5.7485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2239
_refine_ls_wR_factor_ref         0.2532
_reflns_number_gt                13790
_reflns_number_total             20722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052184bsi20060112_030748.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4021549