Direct synthesis of 2-arylazulenes by [8+2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with silyl enol ethers.
Shoji, Taku; Sugiyama, Shuhei; Kobayashi, Yoshiaki; Yamazaki, Akari; Ariga, Yukino; Katoh, Ryuzi; Wakui, Hiroki; Yasunami, Masafumi; Ito, Shunji; Chemical communications (Cambridge, England) 56 (2020) 1485–1488; doi:10.1039/c9cc09376a

data_7125684
_publ_section_title
;
 Direct synthesis of 2-arylazulenes by [8+2] cycloaddition of
 2H-cyclohepta[b]furan-2-ones with silyl enol ethers.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1485
_journal_page_last               1488
_journal_paper_doi               10.1039/c9cc09376a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C15 H13 N'
_chemical_formula_sum            'C15 H13 N'
_chemical_formula_weight         207.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-12-07 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.605(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9324(5)
_cell_length_b                   5.7383(3)
_cell_length_c                   21.1175(13)
_cell_measurement_reflns_used    6995
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.22
_cell_measurement_theta_min      2.26
_cell_volume                     1070.23(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3.1 (Rigaku, 2018)'
_computing_publication_material  'CrystalStructure 4.3.1 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17392
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.994
_diffrn_reflns_theta_min         1.951
_diffrn_source                   'rotating anode X-ray generator'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+1.1639P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1694
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1827
_reflns_number_total             2582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09376a2.cif
_cod_data_source_block           shelxl_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7125682--7125685.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7125684
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_checksum              75096