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_1572852
_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         'C31 H46 N4 Si'
_chemical_formula_sum            'C31 H46 N4 Si'
_chemical_formula_weight         502.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-06-17 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.065(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2595(8)
_cell_length_b                   19.2221(14)
_cell_length_c                   16.2971(13)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.20
_cell_measurement_theta_min      2.33
_cell_volume                     3072.4(4)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1501
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            162231
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.356
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.101
_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    1.087
_exptl_crystal_description       needle
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.1553
_exptl_transmission_factor_min   0.1069
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         7424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+2.2681P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5325
_reflns_number_total             7424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05740f2.cif
_cod_data_source_block           mo_IdippTMSCHN2_07_06_0ma_a
_cod_depositor_comments
'Adding full bibliography for 1572840--1572853.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1572852
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              62465
_shelx_hkl_checksum              91468