A Formal Metal-Free N-Arylation via the Schmidt Reaction of Aromatic Aldehydes with an Azido Amine.
Gu, Peiming; Sun, Jian; Kang, Xiao-Yan; Yi, Ming; Li, Xue-Qiang; Xue, Ping; Li, Rui; Organic letters 15 (2013) 1124–1127; doi:10.1021/ol400213f

data_1508965
_publ_section_title
;
 A Formal Metal-Free N-Arylation via the Schmidt Reaction of Aromatic
 Aldehydes with an Azido Amine.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1124
_journal_page_last               1127
_journal_paper_doi               10.1021/ol400213f
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C17 H19 Br N2 O3 S'
_chemical_formula_sum            'C17 H19 Br N2 O3 S'
_chemical_formula_weight         411.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-10-29
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.725(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0215(15)
_cell_length_b                   5.7478(3)
_cell_length_c                   19.227(6)
_cell_measurement_reflns_used    2801
_cell_measurement_temperature    112(19)
_cell_measurement_theta_max      28.5323
_cell_measurement_theta_min      3.1262
_cell_volume                     1758.4(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      112(19)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9722
_diffrn_measurement_details
;
  1 omega  -31.00    4.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492   57.0000   60.0000 35

  2 omega  -41.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000  -90.0000 127

  3 omega  -35.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000   60.0000 59
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0306093000
_diffrn_orient_matrix_UB_12      0.0883458000
_diffrn_orient_matrix_UB_13      -0.0083086000
_diffrn_orient_matrix_UB_21      -0.0026569000
_diffrn_orient_matrix_UB_22      0.0174552000
_diffrn_orient_matrix_UB_23      0.0360992000
_diffrn_orient_matrix_UB_31      0.0324084000
_diffrn_orient_matrix_UB_32      0.0848810000
_diffrn_orient_matrix_UB_33      0.0012158000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5976
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.14
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+0.8899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0828
_reflns_number_gt                2866
_reflns_number_total             3322
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400213f_si_001.cif
_cod_data_source_block           gupm1026_2
_cod_original_cell_volume        1758.3(6)
_cod_database_code               1508965
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32