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_7122329
_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         'C13 H15 N5'
_chemical_formula_sum            'C13 H15 N5'
_chemical_formula_weight         241.30
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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
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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                90.00
_cell_angle_beta                 96.656(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0745(8)
_cell_length_b                   9.2802(7)
_cell_length_c                   11.0512(6)
_cell_measurement_reflns_used    1326
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.5720
_cell_measurement_theta_min      4.0460
_cell_volume                     1229.98(14)
_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      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -99.00  -60.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000 -180.0000 39

  2 omega   -2.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000    0.0000 65

  3 omega  -37.00   80.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000    0.0000 117
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0111350000
_diffrn_orient_matrix_UB_12      -0.0577031000
_diffrn_orient_matrix_UB_13      0.0389164000
_diffrn_orient_matrix_UB_21      -0.0045885000
_diffrn_orient_matrix_UB_22      0.0496403000
_diffrn_orient_matrix_UB_23      0.0479534000
_diffrn_orient_matrix_UB_31      -0.0579006000
_diffrn_orient_matrix_UB_32      0.0071860000
_diffrn_orient_matrix_UB_33      -0.0189690000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4342
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78590
_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    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0350P)^2^+0.3021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                1913
_reflns_number_total             2421
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc06324a2.cif
_cod_data_source_block           lilh_0507
_cod_depositor_comments
'Adding full bibliography for 7122325--7122329.cif.'
_cod_database_code               7122329
_reflns_odcompleteness_completeness 99.66
_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
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C7(H7), C5(H5), C2(H2), C4(H4), C3(H3)
;
_olex2_date_sample_data_collection 2018-05-07
_olex2_submission_special_instructions 'No special instructions were received'