Preference for the Diels–Alder addition of dienes <i>syn</i> to the O atom in cross-conjugated spirocyclic cyclohexadienones
Gallucci, Judith C.; Tamura, Yukiko; Paquette, Leo A.; Acta Crystallographica Section C 60 (2004) o656–o658; doi:10.1107/S0108270104015951

data_2014148
_publ_section_title
;
 Preference for the Diels--Alder addition of dienes <i>syn</i> to the O
 atom in cross-conjugated spirocyclic cyclohexadienones
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o656
_journal_page_last               o658
_journal_paper_doi               10.1107/S0108270104015951
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C27 H20 O3'
_chemical_formula_moiety         'C27 H20 O3'
_chemical_formula_sum            'C27 H20 O3'
_chemical_formula_weight         392.43
_chemical_name_systematic
;
rel-(1R,4aR,9S,9aS,10R)-4a,9,9a,10-tetrahydro-9,10-diphenylspiro[9,10-
epoxyanthracene-1(4H),2'-oxiran]-4--one
;
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 110.254(4)
_cell_angle_gamma                90.00
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_cell_length_b                   14.2390(10)
_cell_length_c                   14.1380(10)
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_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.04
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_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  reference?
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w 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  0.036
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
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_diffrn_reflns_limit_k_min       -18
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_diffrn_reflns_limit_l_min       -18
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_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
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_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
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_refine_diff_density_min         -0.228
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_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.4364P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1178
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_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fr1490.cif
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_cod_original_cell_volume        1949.3(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2014148
_cod_database_fobs_code          2014148