Metal-free oxidative olefination of primary amines with benzylic C-H bonds through direct deamination and C-H bond activation.
Gong, Liang; Xing, Li-Juan; Xu, Tong; Zhu, Xue-Ping; Zhou, Wen; Kang, Ning; Wang, Bin; Organic & biomolecular chemistry 12 (2014) 6557–6560; doi:10.1039/c4ob01025f

data_7153990
_publ_section_title
;
 Metal-free oxidative olefination of primary amines with benzylic C-H
 bonds through direct deamination and C-H bond activation.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6557
_journal_page_last               6560
_journal_paper_doi               10.1039/c4ob01025f
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C17 H13 N'
_chemical_formula_sum            'C17 H13 N'
_chemical_formula_weight         231.28
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   constr
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.264(19)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   6.6680(16)
_cell_length_b                   19.172(3)
_cell_length_c                   14.717(2)
_cell_measurement_reflns_used    7125
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      1.40
_cell_volume                     1870.2(6)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17402
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.751
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.239
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0723
_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^)+(0.0337P)^2^+1.8300P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1536
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3169
_reflns_number_total             3280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_duplicate_entry             7153951
_cod_data_source_file            c4ob01025f2.cif
_cod_data_source_block           shelxl
_cod_database_code               7153990
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-2
_shelx_res_checksum              23273
_shelx_hkl_checksum              29847