A catalytic intramolecular nitrene insertion into a copper(i)-N-heterocyclic carbene bond yielding fused nitrogen heterocycles.
Fauché, Kévin; Nauton, Lionel; Jouffret, Laurent; Cisnetti, Federico; Gautier, Arnaud; Chemical communications (Cambridge, England) 53 (2017) 2402–2405; doi:10.1039/c6cc09160a

data_7119572
_publ_section_title
;
 A catalytic intramolecular nitrene insertion into a
 copper(i)-N-heterocyclic carbene bond yielding fused nitrogen
 heterocycles.
;
_journal_issue                   15
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2402
_journal_page_last               2405
_journal_paper_doi               10.1039/c6cc09160a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C15 H12 N4'
_chemical_formula_weight         248.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-01-27 deposited with the CCDC.
2017-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8271(7)
_cell_length_b                   12.4492(14)
_cell_length_c                   16.779(2)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.99
_cell_measurement_theta_min      2.93
_cell_volume                     1217.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            73330
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.207
_diffrn_reflns_theta_min         3.273
_diffrn_source                   molybdene
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.99369
_exptl_absorpt_correction_T_min  0.95928
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       platelet
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.710
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1739 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         4485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0647P)^2^+0.1038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0949
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                4255
_reflns_number_total             4485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc09160a2.cif
_cod_data_source_block           C15N4H12
_cod_depositor_comments
'Adding full bibliography for 7119572--7119573.cif.'
_cod_database_code               7119572
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              48743