Geminal Diazides Derived from 1,3-Dicarbonyls: A Protocol for Synthesis.
Erhardt, Hellmuth; Häring, Andreas P; Kotthaus, Andreas; Roggel, Markus; Tong, My Linh; Biallas, Phillip; Jübermann, Martin; Mohr, Fabian; Kirsch, Stefan F.; The Journal of organic chemistry 80 (2015) 12460–12469; doi:10.1021/acs.joc.5b02328

data_4036505
_publ_section_title
;
 Geminal Diazides Derived from 1,3-Dicarbonyls: A Protocol for Synthesis.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12460
_journal_page_last               12469
_journal_paper_doi               10.1021/acs.joc.5b02328
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C13 H14 N6 O3'
_chemical_formula_sum            'C13 H14 N6 O3'
_chemical_formula_weight         302.30
_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   difmap
_audit_creation_date             2015-05-15
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:32:32, GUI svn.r4372)
;
_cell_angle_alpha                103.936(5)
_cell_angle_beta                 91.136(5)
_cell_angle_gamma                111.334(5)
_cell_formula_units_Z            2
_cell_length_a                   8.3623(5)
_cell_length_b                   9.5799(5)
_cell_length_c                   10.5979(6)
_cell_measurement_reflns_used    2859
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.7550
_cell_measurement_theta_min      2.3590
_cell_volume                     762.10(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2705
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.8298
_diffrn_measurement_details
;
  1 omega   14.00   83.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805   57.0000  -30.0000 69

  2 omega   21.00   49.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805  -99.0000   90.0000 28

  3 omega  -42.00   15.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805  -57.0000   60.0000 57

  4 omega   10.00   51.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805   57.0000   30.0000 41

  5 omega    0.00   78.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805   57.0000 -180.0000 78

  6 omega    7.00   63.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805   57.0000  -90.0000 56

  7 omega  -47.00   11.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805  -57.0000 -180.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0916660000
_diffrn_orient_matrix_UB_12      0.0296174000
_diffrn_orient_matrix_UB_13      0.0063725000
_diffrn_orient_matrix_UB_21      -0.0023065000
_diffrn_orient_matrix_UB_22      -0.0102947000
_diffrn_orient_matrix_UB_23      -0.0686626000
_diffrn_orient_matrix_UB_31      0.0017582000
_diffrn_orient_matrix_UB_32      0.0762723000
_diffrn_orient_matrix_UB_33      0.0082580000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6417
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         29.46
_diffrn_reflns_theta_min         1.99
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0422P)^2^+0.1619P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                2776
_reflns_number_total             3519
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02328_si_001.cif
_cod_data_source_block           ocahiv173a
_cod_original_cell_volume        762.10(7)
_cod_database_code               4036505
_chemical_oxdiff_formula         C13H14N6O3
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H7 of C7, H4 of C4, H6 of C6, H5 of C5, H8 of C8
 At 1.5 times of:
  {H12A,H12B,H12C} of C12, {H11A,H11B,H11C} of C11, {H13A,H13B,H13C} of C13
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C4(H4), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;