Substituted 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctenes: syntheses, properties, and DFT studies of substituted Sondheimer-Wong diynes.
Xu, Feng; Peng, Lifen; Shinohara, Kenta; Morita, Takamoto; Yoshida, Suguru; Hosoya, Takamitsu; Orita, Akihiro; Otera, Junzo; The Journal of organic chemistry 79 (2014) 11592–11608; doi:10.1021/jo502248p

data_4030643
_publ_section_title
;
 Substituted 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctenes: syntheses,
 properties, and DFT studies of substituted Sondheimer-Wong diynes.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11592
_journal_page_last               11608
_journal_paper_doi               10.1021/jo502248p
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C13 H10 N2 O'
_chemical_formula_sum            'C13 H10 N2 O'
_chemical_formula_weight         210.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.663(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3806(8)
_cell_length_b                   16.057(2)
_cell_length_c                   9.1541(10)
_cell_measurement_reflns_used    14563
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.54
_cell_volume                     1021.6(2)
_computing_cell_refinement       'APEX2 v.2013.6-2, Bruker/Nonius'
_computing_data_collection       'APEX2 v.2013.6-2, Bruker/Nonius'
_computing_data_reduction        'APEX2 v.2013.6-2, Bruker/Nonius'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      122(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_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  0.1096
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14563
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0453P)^2^+0.3068P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                1487
_reflns_number_total             2252
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502248p_si_003.cif
_cod_data_source_block           mo_d8v662_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4030643