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_7153070
_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.
;
_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           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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 114.543(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.757(2)
_cell_length_b                   10.0250(13)
_cell_length_c                   19.754(3)
_cell_measurement_reflns_used    3922
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.36
_cell_volume                     3378.9(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0665
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12307
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0676P)^2^+2.0152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1676
_reflns_number_gt                2137
_reflns_number_total             4212
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40977e.txt
_cod_data_source_block           T14
_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.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3378.8(7)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7153070