Brønsted Acid-Catalyzed Hydroarylation of Activated Olefins
Fleischer, Ivana; Pospech, Jola; RSC Adv.  (2014) –; doi:10.1039/C4RA13647K

data_7218829
_publ_section_title
;
 Br\/onsted Acid-Catalyzed Hydroarylation of Activated Olefins
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA13647K
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H16 N O1.5'
_chemical_formula_weight         246.30
_chemical_name_systematic        '2-(1-(1H-Indol-3-yl)ethyl)phenol '
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.487(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.2584(3)
_cell_length_b                   5.6362(1)
_cell_length_c                   12.3333(2)
_cell_measurement_reflns_used    7196
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.55
_cell_measurement_theta_min      3.60
_cell_volume                     1263.38(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEX II Duo'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         microfocus
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7959
_diffrn_reflns_theta_full        66.55
_diffrn_reflns_theta_max         66.55
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             524
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: heptane/ethanol'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(18)
_refine_ls_extinction_coef       0.0076(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2229
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0229
_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^)+(0.0386P)^2^+0.2749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0635
_reflns_number_gt                2219
_reflns_number_total             2229
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra13647k2.cif
_cod_data_source_block           ax0389
_cod_original_sg_symbol_H-M      C2
_cod_original_formula_sum        'C16 H16 N O1.50'
_cod_database_code               7218829