Thermal cycloaddition reactions of azulene-1,5-quinones and azulene-1,7-quinones with cyclic dienes and cycloheptatriene
Mori, Akira; Yan, Yong Zhe; Kato, Nobuo; Takeshita, Hitoshi; Nozoe, Tetsuo; Journal of the Chemical Society, Perkin Transactions 1  (1999) 2129–; doi:10.1039/a902493j

data_7213068
_publ_section_title
;
 Thermal cycloaddition reactions of azulene-1,5-quinones and
 azulene-1,7-quinones with cyclic dienes and cycloheptatriene
;
_journal_issue                   15
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2129
_journal_paper_doi               10.1039/a902493j
_journal_year                    1999
_chemical_formula_moiety         'C26 H17 Br O4'
_chemical_formula_sum            'C26 H17 Br O4'
_chemical_formula_weight         473.32
_chemical_melting_point          195
_chemical_name_systematic
; 
 (5_a,6_b,9a_a,10_a,15_a,16_b,17_a)-15a-Bromo-
5,6,9a,10,15,15a,16,17-octahydro-5,17:10,15-diepoxy-
6,16-methanobenzo[5',6']cyclodeca[2',1'-3,4]cyclopenta
[1,2-b]naphthaleno-9,18-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.699(2)
_cell_length_b                   16.985(2)
_cell_length_c                   9.715(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      42
_cell_measurement_theta_min      22
_cell_volume                     2051.5(6)
_computing_cell_refinement       ' CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_collection       ' CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        ' MolEN (Fair, 1990)'
_computing_molecular_graphics    'Xtal_GX (Hall & du Boulay, 1995)'
_computing_publication_material  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution
; SIR92 (Altomare, Burla, Camalli, Cascarano, Giacovazzo, 
Guagliardi & Polidori, 1994) 
;
_diffrn_ambient_temperature      296(2)
_diffrn_measurement_device_type  'Enraf-Nonius FR590'
_diffrn_measurement_method       \w--2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3706
_diffrn_reflns_theta_max         64.95
_diffrn_reflns_theta_min         4.41
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.996
_exptl_absorpt_correction_T_max  0.407
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; empirical via \y scans (North, Phillips, & Mathews, 1968).
Relative values of T max and T min are 0.9998 and 0.8464, respectively.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         .231
_refine_diff_density_min         -.809
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0463P)^2^+1.8952P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                3289
_reflns_number_total             3487
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            902493jsup1.cif
_cod_data_source_block           13
_cod_database_code               7213068