Nickel-Catalyzed Isocyanide Insertion Reaction with Aromatic Amines: Direct Access to Open-Chain Guanidines
Zheng, Zhe; Ma, Hongqiang; Jin, Hongwei; Zhou, Bingwei; Hu, Yuanyuan; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01509J

data_7160903
_publ_section_title
;
 Nickel-Catalyzed Isocyanide Insertion Reaction with Aromatic Amines:
 Direct Access to Open-Chain Guanidines
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01509J
_journal_year                    2025
_chemical_formula_moiety         'C17 H21 N3'
_chemical_formula_sum            'C17 H21 N3'
_chemical_formula_weight         267.376
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-11-25
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-11-25 deposited with the CCDC.	2025-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.518(8)
_cell_angle_beta                 91.336(7)
_cell_angle_gamma                93.881(7)
_cell_formula_units_Z            4
_cell_length_a                   5.9783(10)
_cell_length_b                   10.038(2)
_cell_length_c                   25.696(5)
_cell_measurement_reflns_used    4032
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      27.008
_cell_measurement_theta_min      2.175
_cell_volume                     1538.0(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      223.00
_diffrn_measured_fraction_theta_full 0.9781
_diffrn_measured_fraction_theta_max 0.9783
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.9781
_diffrn_reflns_Laue_measured_fraction_max 0.9783
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6564
_diffrn_reflns_point_group_measured_fraction_full 0.9781
_diffrn_reflns_point_group_measured_fraction_max 0.9783
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.0468
_exptl_absorpt_correction_T_min  0.0239
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1455 before and 0.0703 after correction.
The Ratio of minimum to maximum transmission is 0.5107.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_description       plate
_exptl_crystal_F_000             576.312
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.4974
_refine_diff_density_min         -0.4875
_refine_diff_density_rms         0.1050
_refine_ls_d_res_high            0.8300
_refine_ls_d_res_low             10.0142
_refine_ls_goodness_of_fit_ref   1.0559
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    72
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0559
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.1013
_refine_ls_shift/su_max          -0.0042
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1127P)^2^+3.4041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2740
_refine_ls_wR_factor_ref         0.2901
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                4038
_reflns_number_total             5512
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob01509j2.cif
_cod_data_source_block           mo_JS_10045_0m_tw
_cod_original_cell_volume        1537.9(5)
_cod_database_code               7160903
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9970(7)
 0.0030(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N4(H4), N5(H5), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29),
 C31(H31), C32(H32), C33(H33), C34(H34), C1(H1), N1(H1a), N2(H2), C2(H2a),
 C3(H3), C5(H5a), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
3.b Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C20(H20a,H20b,H20c), C21(H21a,H21b,H21c), C14(H14a,H14b,
 H14c), C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
;
_olex2_submission_special_instructions 'No special instructions were received'