Electronic effects on a one-pot aromatization cascade involving alkynyl-Prins cyclization, Friedel–Crafts alkylation and dehydration to tricyclic benzo[f]isochromenes
Hinkle, Robert J.; Chen, Yuzhou; Nofi, Colleen P.; Lewis, Shane E.; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01412K

data_7155858
_publ_section_title
;
 Electronic effects on a one-pot aromatization cascade involving
 alkynyl-Prins cyclization, Friedel--Crafts alkylation and dehydration to
 tricyclic benzo[f]isochromenes
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01412K
_journal_year                    2017
_chemical_formula_moiety         'C23 H23 Br O'
_chemical_formula_sum            'C23 H23 Br O'
_chemical_formula_weight         395.32
_chemical_name_systematic
'(+-)-4-(4-bromophenyl)-2,2,7,10-tetramethyl-1,4-dihydro-2H-benzo[f]isochromene (2dA)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-06-08 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.9170(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0425(3)
_cell_length_b                   6.45510(10)
_cell_length_c                   17.1404(3)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.27
_cell_measurement_theta_min      3.48
_cell_volume                     1875.59(5)
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2004)'
_computing_data_reduction        SAINTPLUS
_computing_molecular_graphics    'SHELXLE (Hubschle, 2011)'
_computing_publication_material  'Mercury 3.1 (CCDC, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\w and \y'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20549
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.992
_diffrn_reflns_theta_min         3.482
_exptl_absorpt_coefficient_mu    3.026
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4086
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.555
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.189
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0242
_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^)+(0.0360P)^2^+1.3958P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0656
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3257
_reflns_number_total             3309
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01412k2.cif
_cod_data_source_block           P21onn
_cod_database_code               7155858
_shelx_estimated_absorpt_t_min   0.284
_shelx_estimated_absorpt_t_max   0.599
_shelxl_version_number           2013-2
_shelx_res_checksum              22944
_shelx_hkl_checksum              75881