Catalytic double hydroarylation of alkynes to 9,9-disubstituted 9,10-dihydroacridine derivatives by an electrophilic phenoxyphosphonium dication
LaFortune, James H. W.; Bayne, Julia M.; Johnstone, Timothy C.; Fan, Louie; Stephan, Douglas W.; Chemical Communications  (2017) –; doi:10.1039/C7CC08037A

data_7120873
_publ_section_title
;
 Catalytic double hydroarylation of alkynes to 9,9-disubstituted
 9,10-dihydroacridine derivatives by an electrophilic phenoxyphosphonium
 dication
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C7CC08037A
_journal_year                    2017
_chemical_formula_sum            'C23 H22 Br N'
_chemical_formula_weight         392.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_Hall           'I 2 -2c'
_space_group_name_H-M_alt        'I b a 2'
_symmetry_space_group_name_Hall  'I 2 -2c'
_symmetry_space_group_name_H-M   'I b a 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-10-17 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.530(13)
_cell_length_b                   25.541(14)
_cell_length_c                   7.450(4)
_cell_measurement_reflns_used    5456
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.29
_cell_measurement_theta_min      2.54
_cell_volume                     3906(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1183
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27208
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.828
_diffrn_reflns_theta_min         1.595
_exptl_absorpt_coefficient_mu    2.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       SHARD
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.192(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3953
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0468P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2843
_reflns_number_total             3953
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc08037a2.cif
_cod_data_source_block           JL023_iba2
_cod_database_code               7120873
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.227
_shelx_estimated_absorpt_t_max   0.678
_shelx_res_checksum              37149