Friedel-Crafts Alkylation of Indoles with p-Quinols: The Role of Hydrogen Bonding of Water for the Desymmetrization of the Cyclohexadienone System.
García-García, Carolina; Ortiz-Rojano, Laura; Álvarez, Susana; Álvarez, Rosana; Ribagorda, María; Carreño, M Carmen; Organic letters 18 (2016) 2224–2227; doi:10.1021/acs.orglett.6b00781

data_1555539
_publ_section_title
;
 Friedel-Crafts Alkylation of Indoles with p-Quinols: The Role of Hydrogen
 Bonding of Water for the Desymmetrization of the Cyclohexadienone System.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2224
_journal_page_last               2227
_journal_paper_doi               10.1021/acs.orglett.6b00781
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C16 H15 Br Cl3 N O2'
_chemical_formula_weight         439.55
_chemical_name_common            L206
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                76.9570(10)
_cell_angle_beta                 81.0660(10)
_cell_angle_gamma                75.3020(10)
_cell_formula_units_Z            2
_cell_length_a                   7.50910(10)
_cell_length_b                   10.1225(2)
_cell_length_c                   12.5419(2)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      27.2936
_cell_measurement_theta_min      2.8197
_cell_volume                     893.46(3)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25128
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    2.756
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.878
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0994P)^2^+0.8195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1460
_reflns_number_gt                2979
_reflns_number_total             3268
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00781_si_003.cif
_cod_data_source_block           I
_cod_database_code               1555539