Synthesis of Energetic Nitrocarbamates from Polynitro Alcohols and Their Potential as High Energetic Oxidizers.
Axthammer, Quirin J.; Krumm, Burkhard; Klapötke, Thomas M; The Journal of organic chemistry 80 (2015) 6329–6335; doi:10.1021/acs.joc.5b00655

data_4031085
_publ_section_title
;
 Synthesis of Energetic Nitrocarbamates from Polynitro Alcohols and Their
 Potential as High Energetic Oxidizers.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6329
_journal_page_last               6335
_journal_paper_doi               10.1021/acs.joc.5b00655
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C4 H6 N4 O8'
_chemical_formula_sum            'C4 H6 N4 O8'
_chemical_formula_weight         238.113
_chemical_name_common            '2,2-dinitropropyl nitrocarbamate'
_chemical_name_systematic        '2,2-dinitropropyl nitrocarbamate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
;
'Wed Jul 30 17:24:56 2014'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.824(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4551(6)
_cell_length_b                   6.2566(2)
_cell_length_c                   9.7445(4)
_cell_measurement_reflns_used    2110
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.0400
_cell_measurement_theta_min      5.0920
_cell_volume                     906.55(6)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
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_computing_molecular_graphics
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'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
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_computing_publication_material
'PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   23.00   95.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   38.0000  -30.0000 72

  2 omega   55.00   81.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   57.0000    0.0000 26

  3 omega   46.00   85.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   38.0000  -90.0000 39

  4 omega   15.00  103.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   38.0000 -150.0000 88

  5 omega   25.00   74.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000  -30.0000 49

  6 omega   27.00   73.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000 -150.0000 46

  7 omega  -89.00  -34.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000  -60.0000 55

  8 omega -108.00  -32.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  179.0000    0.0000 76

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      -0.0462781000
_diffrn_orient_matrix_UB_12      -0.0273561000
_diffrn_orient_matrix_UB_13      -0.0190560000
_diffrn_orient_matrix_UB_21      0.0096193000
_diffrn_orient_matrix_UB_22      -0.0882155000
_diffrn_orient_matrix_UB_23      0.0474695000
_diffrn_orient_matrix_UB_31      -0.0063573000
_diffrn_orient_matrix_UB_32      0.0658044000
_diffrn_orient_matrix_UB_33      0.0557348000
_diffrn_radiation_collimation    0.5
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6513
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.19
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.7446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_parameters     169
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0351P)^2^+0.2302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                1574
_reflns_number_total             1849
_reflns_threshold_expression     >2\s(I)
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_cod_data_source_block           3d
_cod_depositor_comments
'Adding full bibliography for 4031080--4031086.cif.'
_cod_database_code               4031085
loop_