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_7122325
_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 H17 N5'
_chemical_formula_sum            'C13 H17 N5'
_chemical_formula_weight         243.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-03-07
_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                90.00
_cell_angle_beta                 106.224(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.970(2)
_cell_length_b                   7.2564(6)
_cell_length_c                   17.3888(17)
_cell_measurement_reflns_used    1473
_cell_measurement_temperature    290.04(10)
_cell_measurement_theta_max      68.6910
_cell_measurement_theta_min      4.3910
_cell_volume                     2540.6(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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_environment      air
_diffrn_ambient_temperature      290.04(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -8.00  19.00   1.50    2.00    --    0.00  57.00-120.00   18
  2  \w     22.00  49.00   1.50    2.00    --    0.00  57.00-120.00   18
  3  \w     28.00 115.00   1.50    2.00    --   54.00  38.00 -30.00   58
  4  \w     88.00 178.00   1.50    4.00    --  108.00  25.00-120.00   60
  5  \w    117.00 166.50   1.50    4.00    --  108.00 111.00 -90.00   33
  6  \w    123.00 150.00   1.50    4.00    --  108.00 178.00  30.00   18
  7  \w     96.00 130.50   1.50    4.00    --  108.00  63.00 -90.00   23
  8  \w     85.00 178.00   1.50    4.00    --  108.00  38.00 -30.00   62
  9  \w     89.00 134.00   1.50    4.00    --  108.00 -38.00 -60.00   30
 10  \w     69.00 114.00   1.50    4.00    --  108.00-111.00-180.00   30
 11  \w     40.00 137.50   1.50    4.00    --  108.00 -77.00-180.00   65
 12  \w     39.00 108.00   1.50    2.00    --   54.00-125.00   0.00   46
 13  \w     40.00  70.00   1.50    4.00    --  108.00 -38.00 -60.00   20
 14  \w    -18.00  79.50   1.50    2.00    --   54.00 -38.00 150.00   65
 15  \w     32.00  63.50   1.50    2.00    --    0.00  57.00 150.00   21
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0674408000
_diffrn_orient_matrix_UB_12      -0.0066905000
_diffrn_orient_matrix_UB_13      0.0189864000
_diffrn_orient_matrix_UB_21      0.0355213000
_diffrn_orient_matrix_UB_22      0.0263321000
_diffrn_orient_matrix_UB_23      0.0896870000
_diffrn_orient_matrix_UB_31      -0.0065922000
_diffrn_orient_matrix_UB_32      0.2105332000
_diffrn_orient_matrix_UB_33      -0.0107350000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4434
_diffrn_reflns_theta_full        69.99
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         4.39
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0521P)^2^+0.2389P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                1798
_reflns_number_total             2362
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc06324a2.cif
_cod_data_source_block           lilh_0306_2
_cod_depositor_comments
'Adding full bibliography for 7122325--7122329.cif.'
_cod_database_code               7122325
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;
_olex2_date_sample_data_collection 2018-03-06
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.412
_oxdiff_exptl_absorpt_empirical_full_min 0.710