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_4030642
_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_sum            'C20 H16 N2'
_chemical_formula_weight         284.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.997(2)
_cell_angle_beta                 72.905(2)
_cell_angle_gamma                74.292(2)
_cell_formula_units_Z            4
_cell_length_a                   10.8173(5)
_cell_length_b                   10.9150(6)
_cell_length_c                   14.5641(7)
_cell_measurement_reflns_used    6399
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.78
_cell_volume                     1545.89(14)
_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 0.688
_diffrn_measured_fraction_theta_max 0.688
_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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6399
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0455P)^2^+1.2379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                3809
_reflns_number_total             5074
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502248p_si_002.cif
_cod_data_source_block           mo_d8v299_0m
_cod_original_cell_volume        1545.89(13)
_cod_database_code               4030642