Ag(I)-Promoted homo-dimerization of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes <i>via</i> a [4 + 2] cycloaddition of benzopyrylium ions: access to structurally unique naphthalenes.
Baire, Beeraiah; Santhi, Jampani; Organic & biomolecular chemistry 20 (2021) 247–251; doi:10.1039/d1ob02229f

data_7158429
_publ_section_title
;
 Ag(I)-Promoted homo-dimerization of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes
 <i>via</i> a [4 + 2] cycloaddition of benzopyrylium ions: access to
 structurally unique naphthalenes.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              247
_journal_page_last               251
_journal_paper_doi               10.1039/d1ob02229f
_journal_volume                  20
_journal_year                    2021
_chemical_formula_sum            'C33 H18 Br2 O'
_chemical_formula_weight         590.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-11-13 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 122.657(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5539(7)
_cell_length_b                   17.8625(8)
_cell_length_c                   12.4649(9)
_cell_measurement_temperature    296(2)
_cell_volume                     2540.8(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7587
_diffrn_reflns_point_group_measured_fraction_full 0.824
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        24.828
_diffrn_reflns_theta_max         24.828
_diffrn_reflns_theta_min         2.118
_exptl_absorpt_coefficient_mu    3.215
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 897 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3604
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0177P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_full    0.648
_reflns_Friedel_fraction_max     0.648
_reflns_number_gt                2513
_reflns_number_total             3604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02229f2.cif
_cod_data_source_block           17
_cod_depositor_comments
'Adding full bibliography for 7158428--7158430.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7158429
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.500
_shelx_estimated_absorpt_t_max   0.739
_shelx_res_checksum              85209