Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation.
Vita, Maria Victoria; Caramenti, Paola; Waser, Jerome; Organic letters 17 (2015) 5832–5835; doi:10.1021/acs.orglett.5b03002

data_1555439
_publ_section_title
;
 Enantioselective Synthesis of Homoallylic Azides and Nitriles via
 Palladium-Catalyzed Decarboxylative Allylation.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5832
_journal_page_last               5835
_journal_paper_doi               10.1021/acs.orglett.5b03002
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             31-07-2015
_audit_creation_method           'SHELXL-2014/7, STOE X-RED'
_cell_angle_alpha                90
_cell_angle_beta                 92.659(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0716(5)
_cell_length_b                   6.6011(3)
_cell_length_c                   13.3983(10)
_cell_measurement_reflns_used    10795
_cell_measurement_temperature    292
_cell_measurement_theta_max      67.22
_cell_measurement_theta_min      3.30
_cell_volume                     624.76(7)
_computing_cell_refinement       'X_Area, 1.36 (Stoe, 2006)'
_computing_data_collection       'X_Area, 1.36 (Stoe, 2006)'
_computing_data_reduction        'X_Area, 1.36 (Stoe, 2006)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004 (Burla, XXXX)'
_diffrn_ambient_temperature      292
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      ' 904 frames, detector distance = 40 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6532
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         67.937
_diffrn_reflns_theta_min         3.302
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  0.9372
_exptl_absorpt_correction_T_min  0.7555
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Stoe XRed32 1.31, Stoe (2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       Block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.588
_exptl_crystal_size_mid          0.333
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2171
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0599P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                1917
_reflns_number_total             2171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03002_si_001.cif
_cod_data_source_block           global
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555439
_audit_contact_author            'Kurt J. Schenk'
_shelx_res_checksum              11718
_shelx_hkl_checksum              63615