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_1572840
_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 H48 N4 Si'
_chemical_formula_sum            'C31 H48 N4 Si'
_chemical_formula_weight         504.82
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'Difference Fourier'
_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                86.625(9)
_cell_angle_beta                 85.739(10)
_cell_angle_gamma                72.015(11)
_cell_formula_units_Z            2
_cell_length_a                   8.281(4)
_cell_length_b                   10.126(5)
_cell_length_c                   19.388(8)
_cell_measurement_reflns_used    9785
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.33
_cell_volume                     1540.9(12)
_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  0.108
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6079
_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         25.999
_diffrn_reflns_theta_min         2.108
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.152475
_exptl_absorpt_correction_T_min  0.081178
_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            yellow
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_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0055(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         6079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0713
_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^)+(0.0416P)^2^+2.5847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.1726
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5454
_reflns_number_total             6079
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05740f2.cif
_cod_data_source_block           mo_KB_5_SIPr_TMSCHN2_0m_5
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Direct Method' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1572840--1572853.cif.
;
_cod_original_cell_volume        1541.0(13)
_cod_database_code               1572840
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              26439
_shelx_hkl_checksum              84258