Transition-metal-free multinitrogenation of amides by C-C bond cleavage: a new approach to tetrazoles.
Li, Lian-Hua; Niu, Zhi-Jie; Li, Ying-Xiu; Liang, Yong-Min; Chemical communications (Cambridge, England) 54 (2018) 11148–11151; doi:10.1039/c8cc06324a

data_7122328
_publ_section_title
;
 Transition-metal-free multinitrogenation of amides by C-C bond cleavage:
 a new approach to tetrazoles.
;
_journal_issue                   79
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11148
_journal_page_last               11151
_journal_paper_doi               10.1039/c8cc06324a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C11 H19 N5'
_chemical_formula_sum            'C11 H19 N5'
_chemical_formula_weight         221.31
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-06-28 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                94.814(14)
_cell_angle_beta                 103.101(15)
_cell_angle_gamma                96.922(14)
_cell_formula_units_Z            2
_cell_length_a                   6.8335(13)
_cell_length_b                   9.1979(15)
_cell_length_c                   10.0075(17)
_cell_measurement_reflns_used    802
_cell_measurement_temperature    292.55(10)
_cell_measurement_theta_max      24.1110
_cell_measurement_theta_min      4.0740
_cell_volume                     604.13(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.55(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -87.00  -60.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836  178.0000  120.0000 18

  2 omega -101.00  -59.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836  178.0000  -30.0000 28

  3 omega  -18.00   25.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836  -99.0000 -120.0000 29

  4 omega  -48.00   42.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -57.0000  -30.0000 60

  5 omega   -2.00   52.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -77.0000  120.0000 36

  6 omega  -43.00   98.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430    0.0000  -30.0000 94
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0651268000
_diffrn_orient_matrix_UB_12      -0.0269174000
_diffrn_orient_matrix_UB_13      0.0552556000
_diffrn_orient_matrix_UB_21      -0.0855843000
_diffrn_orient_matrix_UB_22      -0.0386824000
_diffrn_orient_matrix_UB_23      0.0170626000
_diffrn_orient_matrix_UB_31      0.0055574000
_diffrn_orient_matrix_UB_32      -0.0624060000
_diffrn_orient_matrix_UB_33      -0.0449705000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3965
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.55
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.0924P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                1526
_reflns_number_total             2371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc06324a2.cif
_cod_data_source_block           lilh_416_3n3
_cod_depositor_comments
'Adding full bibliography for 7122325--7122329.cif.'
_cod_original_cell_volume        604.14(18)
_cod_database_code               7122328
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H9AA(0.4) H9AB(0.4) H9BC(0.6) H9BD(0.6) C10(0.4) H10A(0.4)
 H10B(0.4) C10'(0.6) H10C(0.6) H10D(0.6)
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B),
 C9(H9AA,H9AB), C9(H9BC,H9BD), C10(H10A,H10B), C10'(H10C,H10D)
;
_olex2_date_sample_data_collection 2018-05-07
_olex2_submission_special_instructions 'No special instructions were received'