Organocatalytic enantioselective and (Z)-selective allylation of 3-indolylmethanol via hydrogen-bond activation
Yan Liu; Hong-Hao Zhang; Yu-Chen Zhang; Yan Jiang; Feng Shi; Shu-Jiang Tu; Chem.Commun. 50 (2014) 12054–; doi:10.1039/C4cc02056A

data_7115712
_publ_section_title
;
 Organocatalytic enantioselective and (Z)-selective allylation of
 3-indolylmethanol via hydrogen-bond activation
;
_journal_name_full               Chem.Commun.
_journal_page_first              12054
_journal_paper_doi               10.1039/C4cc02056A
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H27 Br N2 O2'
_chemical_formula_weight         563.47
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9032(6)
_cell_length_b                   11.1649(7)
_cell_length_c                   27.772(2)
_cell_measurement_reflns_used    2433
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.81
_cell_measurement_theta_min      2.93
_cell_volume                     2760.6(3)
_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  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1014
_diffrn_reflns_av_unetI/netI     0.1366
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24143
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         2.858
_exptl_absorpt_coefficient_mu    1.521
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             1160
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
; 
 Flack x determined using 818 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.025(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         6298
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.1860
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1508
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2682
_reflns_number_total             6298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc02056a2.cif
_cod_data_source_block           SF140220_LY_0m
_cod_database_code               7115712
_shelxl_version_number           2013-4
_shelx_res_checksum              23758
_shelx_hkl_checksum              90829