A facile tandem decyanation/cyanation reaction of α-iminonitriles toward cyano-substituted amides.
Chen, Zhengwang; Liang, Pei; Liu, Botao; Luo, Haiqing; Zheng, Jing; Wen, Xiaowei; Liu, Tanggao; Ye, Min; Organic & biomolecular chemistry 16 (2018) 8481–8485; doi:10.1039/c8ob02186d

data_7156532
_publ_section_title
;
 A facile tandem decyanation/cyanation reaction of \a-iminonitriles toward
 cyano-substituted amides.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8481
_journal_page_last               8485
_journal_paper_doi               10.1039/c8ob02186d
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C13 H9 N3 O'
_chemical_formula_sum            'C13 H9 N3 O'
_chemical_formula_weight         223.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1zx7gl
_audit_creation_date             2018-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-05-19 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.86
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.042
_cell_length_b                   5.681
_cell_length_c                   14.602
_cell_measurement_reflns_used    1876
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.4910
_cell_measurement_theta_min      3.3910
_cell_volume                     1068.976
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11018
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        24.812
_diffrn_reflns_theta_max         24.812
_diffrn_reflns_theta_min         1.580
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_refine_diff_density_max         1.186
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1469
_refine_ls_R_factor_gt           0.1114
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2549
_refine_ls_wR_factor_ref         0.2965
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1187
_reflns_number_total             1780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02186d2.cif
_cod_data_source_block           bb
_cod_depositor_comments          'Adding full bibliography for 7156532.cif.'
_cod_original_cell_volume        1069.0
_cod_database_code               7156532
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), N2(H2A)
;
_shelx_res_checksum              74364
_olex2_submission_special_instructions 'No special instructions were received'