Synthesis of 2,8-Dioxabicyclo[3.3.1]nonane Derivatives via a Sequential Knoevenagel Condensation and Hetero-Diels-Alder Reaction in an Aqueous Medium
Venu Srinivas; Mamoru Koketsu; Journal of Organic Chemistry 78 (2013) 11612–11617; doi:10.1021/jo401990h

data_4028761
_publ_contact_author_address
;Department of Chemistry and Biomolecular Science 
Faculty of Engineering 
Gifu University 
Gifu 501-1193, Japan
;
_publ_contact_author_email       koketsu@gifu-u.ac.jp
_publ_contact_author_fax         +81-58-293-2794
_publ_contact_author_name        'Mamoru Koketsu'
_publ_contact_author_phone       +81-58-293-2619
_publ_section_title
;
 Synthesis of 2,8-Dioxabicyclo[3.3.1]nonane Derivatives via a Sequential
 Knoevenagel Condensation and Hetero-Diels-Alder Reaction in an Aqueous
 Medium
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11612
_journal_page_last               11617
_journal_paper_doi               10.1021/jo401990h
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C17 H17 Br O5'
_chemical_formula_sum            'C17 H17 Br O5'
_chemical_formula_weight         381.21
_chemical_name_common            2,8-Dioxabicyclo[3.3.1]nonane
_chemical_name_systematic
;
 5-acetyl-8-bromo-4-methyl-6H-2,6-methanobenzo[d][1,3]dioxocine-11-carboxylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 107.557(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.335(6)
_cell_length_b                   6.2952(15)
_cell_length_c                   23.129(6)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.8409
_cell_measurement_theta_min      2.7711
_cell_volume                     3239.3(14)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Mercury CCD (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12895
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    2.561
_exptl_absorpt_correction_T_max  0.605
_exptl_absorpt_correction_T_min  0.599
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                3133
_reflns_number_total             3724
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401990h_si_002.cif
_cod_data_source_block           compound_3b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'NUMERICAL' changed to
'numerical' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_database_code               4028761