Practical Synthesis of N-Substituted Cyanamides via Tiemann Rearrangement of Amidoximes.
Lin, Chia-Chi; Hsieh, Tsung-Han; Liao, Pen-Yuan; Liao, Zhen-Yuan; Chang, Chih-Wei; Shih, Yu-Chiao; Yeh, Wen-Hsiung; Chien, Tun-Cheng; Organic letters 16 (2014) 892–895; doi:10.1021/ol403645y

data_1513488
_publ_section_title
;
 Practical Synthesis of N-Substituted Cyanamides via Tiemann Rearrangement
 of Amidoximes.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              892
_journal_page_last               895
_journal_paper_doi               10.1021/ol403645y
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C14 H13 N3 O2 S'
_chemical_formula_sum            'C14 H13 N3 O2 S'
_chemical_formula_weight         287.33
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.652(3)
_cell_angle_beta                 71.319(2)
_cell_angle_gamma                86.053(3)
_cell_formula_units_Z            4
_cell_length_a                   9.7187(4)
_cell_length_b                   10.3158(5)
_cell_length_c                   14.7642(6)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1383.37(11)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11575
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_correction_T_min  0.9106
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0434P)^2^+1.0157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                3460
_reflns_number_total             4863
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403645y_si_004.cif
_cod_data_source_block           a12905
_cod_original_cell_volume        1383.38(10)
_cod_database_code               1513488