Intramolecular benzoallene–alkyne cycloaddition initiated by site-selective SN2’ reaction of epoxytetracene en route to π-extended pyracylene
Hamura, Toshiyuki; Kitamura, Kei; Asahina, Kenta; Adachi, Kazuhiko; Chemical Communications  (2019) –; doi:10.1039/C9CC05500B

data_7124058
_publ_section_title
;
 Intramolecular benzoallene--alkyne cycloaddition initiated by
 site-selective SN2&#x2019; reaction of epoxytetracene en route to
 \p-extended pyracylene
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05500B
_journal_year                    2019
_chemical_formula_moiety         'C52 H31 Br O2, C6 H6'
_chemical_formula_sum            'C58 H37 Br O2'
_chemical_formula_weight         845.78
_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-2014/7
_audit_update_record
;
2019-07-12 deposited with the CCDC.    2019-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                91.289(2)
_cell_angle_beta                 95.8040(10)
_cell_angle_gamma                90.059(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0716(3)
_cell_length_b                   12.9698(4)
_cell_length_c                   15.7503(4)
_cell_measurement_reflns_used    8720
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.06
_cell_measurement_theta_min      3.41
_cell_volume                     2046.33(10)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.1164
_diffrn_reflns_av_unetI/netI     0.1924
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23945
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.204
_diffrn_reflns_theta_min         3.409
_diffrn_source                   'rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    1.725
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.114
_refine_diff_density_min         -0.947
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         7346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.2000
_refine_ls_R_factor_gt           0.1076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1486P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2301
_refine_ls_wR_factor_ref         0.3081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2651
_reflns_number_total             7346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05500b2.cif
_cod_data_source_block           shelxl
_cod_database_code               7124058
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.817
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              72309