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_4031082
_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         'C5 H8 N4 O8'
_chemical_formula_sum            'C5 H8 N4 O8'
_chemical_formula_weight         252.15
_chemical_name_common            '4,4,4-trinitrobutyl carbamate'
_chemical_name_systematic        '4,4,4-trinitrobutyl carbamate'
_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
;
'Fri Apr 04 05:57:03 2014'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.778(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4255(8)
_cell_length_b                   10.2488(6)
_cell_length_c                   7.4690(5)
_cell_measurement_reflns_used    1919
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.2600
_cell_measurement_theta_min      4.8180
_cell_volume                     1022.48(11)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 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 0.992
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_diffrn_measurement_details
;
  1 omega -109.00  -61.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000  -60.0000 48

  2 omega  -76.00    2.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  -77.0000  -60.0000 78

  3 omega -104.00   30.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994    0.0000  -60.0000 134

  4 omega   25.00   93.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932 -130.0000 -137.0000 68

  5 omega   34.00  102.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   77.0000   90.0000 68

  6 omega   60.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  179.0000  -30.0000 31

  7 omega   42.00   67.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932 -179.0000 -120.0000 25

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
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_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      0.0104315000
_diffrn_orient_matrix_UB_12      -0.0038941000
_diffrn_orient_matrix_UB_13      0.0948855000
_diffrn_orient_matrix_UB_21      0.0520301000
_diffrn_orient_matrix_UB_22      -0.0018893000
_diffrn_orient_matrix_UB_23      -0.0093694000
_diffrn_orient_matrix_UB_31      0.0019817000
_diffrn_orient_matrix_UB_32      0.0690509000
_diffrn_orient_matrix_UB_33      0.0051189000
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7159
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         4.37
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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            colorless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         1895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0840P)^2^+0.8635P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1684
_reflns_number_gt                1487
_reflns_number_total             1895
_reflns_threshold_expression     >2\s(I)
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'Adding full bibliography for 4031080--4031086.cif.'
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loop_