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_4031086
_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 H7 N5 O10'
_chemical_formula_sum            'C5 H7 N5 O10'
_chemical_formula_weight         297.16
_chemical_name_common            '4,4,4-trinitrobutyl nitrocarbamate'
_chemical_name_systematic        '4,4,4-trinitrobutyl nitrocarbamate'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Wed Jul 30 09:41:18 2014'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.5690(10)
_cell_length_b                   10.8030(8)
_cell_length_c                   25.5310(5)
_cell_measurement_reflns_used    3051
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.8600
_cell_measurement_theta_min      4.3820
_cell_volume                     2363.4(3)
_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)
;
_computing_data_reduction
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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_molecular_graphics
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'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
;
_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 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega  -89.00   -4.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931  -38.0000  -60.0000 85

  2 omega  -99.00  -39.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931 -179.0000   60.0000 60

  3 omega  -10.00   24.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931  -99.0000   30.0000 34

  4 omega  -23.00   22.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931  -99.0000 -164.0000 45

  5 omega  -89.00  -60.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931 -179.0000  -30.0000 29

  6 omega  -56.00  -29.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931   99.0000  -58.0000 27

  7 omega  -76.00   -6.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931    0.0000  -30.0000 70

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      -0.0781973000
_diffrn_orient_matrix_UB_12      0.0098303000
_diffrn_orient_matrix_UB_13      -0.0080819000
_diffrn_orient_matrix_UB_21      0.0267364000
_diffrn_orient_matrix_UB_22      0.0158531000
_diffrn_orient_matrix_UB_23      -0.0254338000
_diffrn_orient_matrix_UB_31      -0.0053948000
_diffrn_orient_matrix_UB_32      -0.0629067000
_diffrn_orient_matrix_UB_33      -0.0077309000
_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  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13957
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.41
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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    1.6702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_reflns         4786
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0760
_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^)+(0.1435P)^2^+0.0087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2012
_refine_ls_wR_factor_ref         0.2352
_reflns_number_gt                3367
_reflns_number_total             4786
_reflns_threshold_expression     >2\s(I)
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_cod_depositor_comments
'Adding full bibliography for 4031080--4031086.cif.'
_cod_database_code               4031086
loop_