Retro-Claisen benzylation: direct use of benzyl alcohols in Pd-catalyzed couplings with nitriles
Tapan Maji; Kinthada Ramakumar; Jon A. Tunge; Chem.Commun. 50 (2014) 14045–; doi:10.1039/C4cc07001A

data_7115924
_publ_section_title
;
 Retro-Claisen benzylation: direct use of benzyl alcohols in Pd-catalyzed
 couplings with nitriles
;
_journal_name_full               Chem.Commun.
_journal_page_first              14045
_journal_paper_doi               10.1039/C4cc07001A
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C21 H21 N'
_chemical_formula_weight         287.39
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.129(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9040(6)
_cell_length_b                   28.724(2)
_cell_length_c                   8.0911(7)
_cell_measurement_reflns_used    7453
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.11
_cell_measurement_theta_min      3.08
_cell_volume                     1604.5(2)
_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    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker Platinum 135 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9501
_diffrn_reflns_point_group_measured_fraction_full 0.769
_diffrn_reflns_point_group_measured_fraction_max 0.748
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         68.105
_diffrn_reflns_theta_min         3.077
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       'Rectangular parallelepiped'
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
; 
 Flack x determined using 1477 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   1.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         4392
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0269
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+0.2372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0705
_reflns_Friedel_coverage         0.544
_reflns_Friedel_fraction_full    0.559
_reflns_Friedel_fraction_max     0.539
_reflns_number_gt                4256
_reflns_number_total             4392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc07001a2.cif
_cod_data_source_block           v55b_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scan ' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_database_code               7115924
_shelx_estimated_absorpt_t_min   0.816
_shelx_estimated_absorpt_t_max   0.975
_shelxl_version_number           2013-4
_shelx_res_checksum              90600
_shelx_hkl_checksum              85204
_cod_duplicate_entry 7115923