Synthesis of azulene-substituted benzofurans and isocoumarins via intramolecular cyclization of 1-ethynylazulenes, and their structural and optical properties.
Shoji, Taku; Tanaka, Miwa; Takagaki, Sho; Miura, Kota; Ohta, Akira; Sekiguchi, Ryuta; Ito, Shunji; Mori, Shigeki; Okujima, Tetsuo; Organic & biomolecular chemistry 16 (2018) 480–489; doi:10.1039/c7ob02861j

data_7156042
_publ_section_title
;
 Synthesis of azulene-substituted benzofurans and isocoumarins via
 intramolecular cyclization of 1-ethynylazulenes, and their structural and
 optical properties.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              480
_journal_page_last               489
_journal_paper_doi               10.1039/c7ob02861j
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C21 H13 I O4'
_chemical_formula_sum            'C21 H13 I O4'
_chemical_formula_weight         456.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-04-18 deposited with the CCDC.
2017-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                103.6260(17)
_cell_angle_beta                 100.7920(17)
_cell_angle_gamma                99.5738(17)
_cell_formula_units_Z            4
_cell_length_a                   7.76154(16)
_cell_length_b                   14.0693(3)
_cell_length_c                   16.6303(3)
_cell_measurement_reflns_used    18691
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.26
_cell_measurement_theta_min      1.75
_cell_volume                     1691.05(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_publication_material  'CrystalStructure 4.2.4'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28239
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_min         2.259
_diffrn_source                   'Varimax 50 kV 24 mA Rotating anode'
_exptl_absorpt_coefficient_mu    1.918
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.813
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         8138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0258P)^2^+2.4452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0719
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6953
_reflns_number_total             8138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02861j2.cif
_cod_data_source_block           shelxl_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7156040--7156045.cif.'
_cod_database_code               7156042
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.927
_shelx_estimated_absorpt_t_max   0.963
_shelx_res_checksum              69828