#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:30:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180302 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151611.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151611
loop_
_publ_author_name
'Yamamura, Kimiaki'
'Houda, Yuuko'
'Hashimoto, Masao'
'Kimura, Takatomo'
'Kamezawa, Makoto'
'Otani, Takehiko'
_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_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         302.37
_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/[σ²(Fo²)+(0.0762P)²+0.0493P] where P=(Fo²+2Fc²)/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
;
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 
;
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               7151611
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0934(2) 0.2500 0.2865(2) 0.0397(5) Uani 1 2 d S . .
C2 C 0.1322(3) 0.2500 0.1826(3) 0.0557(7) Uani 1 2 d S . .
C3 C 0.0281(4) 0.2500 0.0659(3) 0.0676(9) Uani 1 2 d S . .
C4 C -0.1109(3) 0.2500 0.0527(2) 0.0619(8) Uani 1 2 d S . .
C5 C -0.1501(3) 0.2500 0.1559(2) 0.0487(6) Uani 1 2 d S . .
C6 C -0.0469(2) 0.2500 0.2764(2) 0.0364(5) Uani 1 2 d S . .
C7 C -0.0571(2) 0.2500 0.3984(2) 0.0349(5) Uani 1 2 d S . .
C8 C -0.1605(2) 0.2500 0.4524(2) 0.0353(5) Uani 1 2 d S . .
C9 C -0.3037(3) 0.2500 0.3890(2) 0.0462(6) Uani 1 2 d S . .
C10 C -0.4102(3) 0.2500 0.4365(3) 0.0577(7) Uani 1 2 d S . .
C11 C -0.4005(3) 0.2500 0.5599(3) 0.0596(8) Uani 1 2 d S . .
C12 C -0.2840(3) 0.2500 0.6675(3) 0.0538(7) Uani 1 2 d S . .
C13 C -0.1445(3) 0.2500 0.6814(2) 0.0427(5) Uani 1 2 d S . .
C14 C -0.0849(2) 0.2500 0.5905(2) 0.0356(5) Uani 1 2 d S . .
C15 C 0.0599(2) 0.2500 0.6137(2) 0.0342(5) Uani 1 2 d S . .
C16 C 0.0732(2) 0.2500 0.4951(2) 0.0339(5) Uani 1 2 d S . .
C17 C 0.1698(2) 0.2500 0.7339(2) 0.0379(5) Uani 1 2 d S . .
C18 C 0.3071(3) 0.2500 0.7564(2) 0.0474(6) Uani 1 2 d S . .
C19 C 0.4173(3) 0.2500 0.8800(3) 0.0551(7) Uani 1 2 d S . .
C20 C 0.3800(4) 0.2500 0.9946(3) 0.0697(10) Uani 1 2 d S . .
H1 H 0.231(3) 0.2500 0.188(3) 0.065(8) Uiso 1 2 d S . .
H2 H 0.048(4) 0.2500 -0.007(4) 0.078(10) Uiso 1 2 d S . .
H3 H -0.180(3) 0.2500 -0.023(3) 0.063(9) Uiso 1 2 d S . .
H4 H -0.248(3) 0.2500 0.146(3) 0.050(7) Uiso 1 2 d S . .
H5 H -0.336(3) 0.2500 0.298(3) 0.054(8) Uiso 1 2 d S . .
H6 H -0.509(4) 0.2500 0.378(3) 0.066(9) Uiso 1 2 d S . .
H7 H -0.482(3) 0.2500 0.574(2) 0.054(8) Uiso 1 2 d S . .
H8 H -0.299(3) 0.2500 0.745(3) 0.070(9) Uiso 1 2 d S . .
H9 H -0.081(3) 0.2500 0.762(2) 0.042(7) Uiso 1 2 d S . .
H10 H 0.143(3) 0.2500 0.801(3) 0.054(8) Uiso 1 2 d S . .
H11 H 0.347(3) 0.2500 0.685(3) 0.061(8) Uiso 1 2 d S . .
H12 H 0.331(3) 0.137(4) 1.000(3) 0.117(11) Uiso 1 1 d . . .
H13 H 0.464(5) 0.2500 1.068(4) 0.110(15) Uiso 1 2 d S . .
O1 O 0.5390(2) 0.2500 0.8895(2) 0.0933(9) Uani 1 2 d S . .
S1 S 0.20999(6) 0.2500 0.44182(5) 0.0413(2) Uani 1 2 d S . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.3(2) . . ?
C2 C1 S1 124.8(2) . . ?
C6 C1 S1 112.89(17) . . ?
C3 C2 C1 118.1(3) . . ?
C2 C3 C4 121.1(3) . . ?
C5 C4 C3 121.1(3) . . ?
C4 C5 C6 119.5(3) . . ?
C1 C6 C5 118.0(2) . . ?
C1 C6 C7 110.67(19) . . ?
C5 C6 C7 131.4(2) . . ?
C16 C7 C8 108.1(2) . . ?
C16 C7 C6 112.7(2) . . ?
C8 C7 C6 139.3(2) . . ?
C9 C8 C7 126.5(2) . . ?
C9 C8 C14 127.3(2) . . ?
C7 C8 C14 106.23(18) . . ?
C8 C9 C10 129.2(2) . . ?
C11 C10 C9 128.8(3) . . ?
C12 C11 C10 129.5(3) . . ?
C11 C12 C13 129.3(3) . . ?
C12 C13 C14 129.4(2) . . ?
C13 C14 C15 125.5(2) . . ?
C13 C14 C8 126.5(2) . . ?
C15 C14 C8 108.04(18) . . ?
C14 C15 C16 106.25(18) . . ?
C14 C15 C17 126.3(2) . . ?
C16 C15 C17 127.5(2) . . ?
C7 C16 C15 111.4(2) . . ?
C7 C16 S1 112.96(17) . . ?
C15 C16 S1 135.63(17) . . ?
C18 C17 C15 126.5(2) . . ?
C17 C18 C19 125.5(3) . . ?
O1 C19 C18 120.0(3) . . ?
O1 C19 C20 120.2(3) . . ?
C18 C19 C20 119.8(2) . . ?
C16 S1 C1 90.80(10) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(3) . ?
C1 C6 1.406(3) . ?
C1 S1 1.752(2) . ?
C2 C3 1.380(4) . ?
C3 C4 1.383(5) . ?
C4 C5 1.381(4) . ?
C5 C6 1.407(3) . ?
C6 C7 1.440(3) . ?
C7 C16 1.398(3) . ?
C7 C8 1.412(3) . ?
C8 C9 1.387(3) . ?
C8 C14 1.492(3) . ?
C9 C10 1.389(4) . ?
C10 C11 1.382(4) . ?
C11 C12 1.376(4) . ?
C12 C13 1.385(4) . ?
C13 C14 1.387(3) . ?
C14 C15 1.415(3) . ?
C15 C16 1.416(3) . ?
C15 C17 1.433(3) . ?
C16 S1 1.724(2) . ?
C17 C18 1.341(3) . ?
C18 C19 1.461(3) . ?
C19 O1 1.216(3) . ?
C19 C20 1.497(5) . ?
