An efficient novel synthesis of beta-(azuleno[1,2-b]benzothienyl)- and beta-(azuleno[2,1-b]benzothienyl)-alpha,beta-unsaturated ketones by the tropylium ion-mediated intramolecular furan ring-opening reaction and X-ray investigation of methyl ketone derivative
Yamamura, Kimiaki; Houda, Yuuko; Hashimoto, Masao; Kimura, Takatomo; Kamezawa, Makoto; Otani, Takehiko; Organic & Biomolecular Chemistry 2 (2004) 1413–1418; doi:10.1039/b401579g

data_7151612
_publ_section_title
;
 An efficient novel synthesis of beta-(azuleno[1,2-b]benzothienyl)- and
 beta-(azuleno[2,1-b]benzothienyl)-alpha,beta-unsaturated ketones by
 the tropylium ion-mediated intramolecular furan ring-opening reaction
 and X-ray investigation of methyl ketone derivative
;
_journal_coden_ASTM              OBCRAK
_journal_issue                   9
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1413
_journal_page_last               1418
_journal_paper_doi               10.1039/b401579g
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'benzothiophene, azulene, carbonyl'
_chemical_formula_sum            'C20 H14 O S'
_chemical_formula_weight         302.3
_chemical_melting_point          431
_chemical_name_common
(E)-4-(11-azuleno(1,2-b)benzothiophenyl)-3-butene-2-one
_chemical_name_systematic
(E)-4-(11-azuleno[1,2-b]benzothiophenyl)-3-butene-2-one
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.905(3)
_cell_length_b                   4.7718(7)
_cell_length_c                   33.799(5)
_cell_measurement_temperature    298(2)
_cell_volume                     3049.0(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_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  0.0869
_diffrn_reflns_av_sigmaI/netI    0.1119
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            15383
_diffrn_reflns_theta_full        27.28
_diffrn_reflns_theta_max         27.28
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.60(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5720
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.1765
_refine_ls_R_factor_gt           0.0827
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1310P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1934
_refine_ls_wR_factor_ref         0.2379
_reflns_number_gt                2635
_reflns_number_total             5720
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b401579g.txt
_cod_data_source_block           azul-4a
_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               7151612