A novel and efficient synthesis of diverse dihydronaphtho[1,2-b]furans using the ceric ammonium nitrate-catalyzed formal [3 + 2] cycloaddition of 1,4-naphthoquinones to olefins and its application to furomollugin.
Xia, Likai; Lee, Yong Rok; Organic & biomolecular chemistry 11 (2013) 6097–6107; doi:10.1039/c3ob40977e

data_7153069
_publ_section_title
;
 A novel and efficient synthesis of diverse dihydronaphtho[1,2-b]furans
 using the ceric ammonium nitrate-catalyzed formal [3 + 2] cycloaddition
 of 1,4-naphthoquinones to olefins and its application to furomollugin.
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_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6097
_journal_page_last               6107
_journal_paper_doi               10.1039/c3ob40977e
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C21 H18 O5'
_chemical_formula_sum            'C21 H18 O5'
_chemical_formula_weight         350.35
_space_group_IT_number           14
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_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 102.588(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6513(11)
_cell_length_b                   10.1496(9)
_cell_length_c                   14.4797(14)
_cell_measurement_reflns_used    1265
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      2.47
_cell_volume                     1671.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0993
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_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10313
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.1596
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1716
_reflns_number_gt                1519
_reflns_number_total             3291
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40977e.txt
_cod_data_source_block           C13-a
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7153069