Copper-catalyzed carboxamide-directed ortho amination of anilines with alkylamines at room temperature.
Li, Qiong; Zhang, Shu-Yu; He, Gang; Ai, Zhaoyan; Nack, William A.; Chen, Gong; Organic letters 16 (2014) 1764–1767; doi:10.1021/ol500464x

data_1513919
_publ_section_title
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 Copper-catalyzed carboxamide-directed ortho amination of anilines with
 alkylamines at room temperature.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1764
_journal_page_last               1767
_journal_paper_doi               10.1021/ol500464x
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C15 H16 N4 O2'
_chemical_formula_sum            'C15 H16 N4 O2'
_chemical_formula_weight         284.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 92.289(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.522(3)
_cell_length_b                   15.626(4)
_cell_length_c                   19.401(5)
_cell_measurement_reflns_used    4056
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.903
_cell_measurement_theta_min      2.504
_cell_volume                     2884.4(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0772
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19534
_diffrn_reflns_theta_full        28.48
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         7218
_refine_ls_number_restraints     435
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1518
_refine_ls_R_factor_gt           0.1077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+5.2434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2676
_refine_ls_wR_factor_ref         0.2909
_reflns_number_gt                4537
_reflns_number_total             7218
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500464x_si_003.cif
_cod_data_source_block           suz6s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1513919