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_7151611
_publ_section_title
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 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.
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_journal_issue                   9
_journal_name_full               'Organic &amp; 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         302.37
_chemical_melting_point          393
_chemical_name_common
(E)-4-(11-azuleno(2,1-b)benzothiophenyl)-3-butene-2-one
_chemical_name_systematic
(E)-4-(11-azuleno[2,1-b]benzothiophenyl)-3-butene-2-one
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 111.162(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2869(16)
_cell_length_b                   6.7635(11)
_cell_length_c                   11.4718(18)
_cell_measurement_temperature    289(2)
_cell_volume                     744.3(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      289(2)
_diffrn_measured_fraction_theta_full 0.903
_diffrn_measured_fraction_theta_max 0.903
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3962
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark greenish-brown'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0762P)^2^+0.0493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                1315
_reflns_number_total             1608
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b401579g.txt
_cod_data_source_block           azul-8a
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '393K' was changed to '393' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
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_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               7151611