Uncovering diverse reactivity of NHCs with diazoalkane: C-H activation, C[double bond, length as m-dash]C bond formation, and access to N-heterocyclic methylenehydrazine.
Balayan, Kajal; Sharma, Himanshu; Vanka, Kumar; Gonnade, Rajesh G.; Sen, Sakya S.; Chemical science 15 (2024) 18387–18394; doi:10.1039/d4sc05740f

data_1572841
_publ_section_title
;
 Uncovering diverse reactivity of NHCs with diazoalkane: C-H activation,
 C[double bond, length as m-dash]C bond formation, and access to
 N-heterocyclic methylenehydrazine.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              18387
_journal_page_last               18394
_journal_paper_doi               10.1039/d4sc05740f
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C28 H38 N4'
_chemical_formula_sum            'C28 H38 N4'
_chemical_formula_weight         430.62
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2ybc'
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_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-04-10 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.828(2)
_cell_angle_gamma                90
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_cell_length_a                   19.9625(12)
_cell_length_b                   6.8258(4)
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_cell_measurement_reflns_used    6099
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.20
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_cell_volume                     2602.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
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_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
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_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
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_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1105
_diffrn_reflns_av_unetI/netI     0.1155
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31733
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.026
_diffrn_reflns_theta_min         2.565
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         7569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1640
_refine_ls_R_factor_gt           0.0746
_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^)+(0.0631P)^2^+1.1075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1903
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3965
_reflns_number_total             7569
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           mo_IDippCHN2TMS_0ma_a
_cod_depositor_comments
'Adding full bibliography for 1572840--1572853.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1572841
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              15847
_shelx_hkl_checksum              26245