#------------------------------------------------------------------------------
#$Date: 2021-02-04 02:53:14 +0200 (Thu, 04 Feb 2021) $
#$Revision: 261473 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/56/4135601.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4135601
loop_
_publ_author_name
'Benz, Maximilian'
'Klapötke, Thomas M'
'Krumm, Burkhard'
'Lommel, Marcus'
'Stierstorfer, Jörg'
_publ_section_title
;
 Nitrocarbamoyl Azide O₂NN(H)C(O)N₃: A Stable but
 Highly Energetic Member of the Carbonyl Azide Family.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1323
_journal_page_last               1327
_journal_paper_doi               10.1021/jacs.0c12507
_journal_volume                  143
_journal_year                    2021
_chemical_formula_moiety         'C H4 N4 O3, H2 O'
_chemical_formula_sum            'C H6 N4 O4'
_chemical_formula_weight         138.10
_chemical_name_common            4-nitro-semicarbazid
_chemical_name_systematic        4-nitro-semicarbazid
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     difmap
_audit_creation_date
;
'Wed Jun 15 13:09:44 2016'
;
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5532(3)
_cell_length_b                   6.3625(2)
_cell_length_c                   16.3333(5)
_cell_measurement_reflns_used    2372
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      33.1370
_cell_measurement_theta_min      4.4350
_cell_volume                     992.77(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Encifer 1.5.1, CCDC 2014'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00  103.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       32.0000   79.0000    0.0000 104

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00  103.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       32.0000   79.0000  120.0000 104

#__ type_ start__ end____ width___ exp.time_
  3 omega  -65.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.0000   80.0000  250.0000 104

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0684929000
_diffrn_orient_matrix_UB_12      -0.0387196000
_diffrn_orient_matrix_UB_13      -0.0073386000
_diffrn_orient_matrix_UB_21      -0.0244140000
_diffrn_orient_matrix_UB_22      0.0533678000
_diffrn_orient_matrix_UB_23      0.0353490000
_diffrn_orient_matrix_UB_31      -0.0149543000
_diffrn_orient_matrix_UB_32      0.0898946000
_diffrn_orient_matrix_UB_33      -0.0241454000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5643
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.272
_diffrn_reflns_theta_min         4.267
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95422
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.024(2)
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0371P)²+0.3685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0752
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1088
_reflns_number_total             1238
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c12507_si_001.cif
_cod_data_source_block           lx301
_cod_database_code               4135601
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.18228(8) 0.67226(13) 0.39969(5) 0.0178(2) Uani 1 1 d . . . . .
O4 O 0.37744(8) 0.43337(13) 0.07451(5) 0.0160(2) Uani 1 1 d . . . . .
O1 O 0.21387(8) 0.75992(13) 0.24035(5) 0.0169(2) Uani 1 1 d . . . . .
O3 O 0.37646(8) 0.61019(14) 0.46453(5) 0.0190(2) Uani 1 1 d . . . . .
N4 N 0.31249(9) 0.66392(14) 0.40059(5) 0.0120(2) Uani 1 1 d . . . . .
N3 N 0.39640(9) 0.70764(14) 0.33812(5) 0.0124(2) Uani 1 1 d . . . . .
N2 N 0.40163(10) 0.84187(15) 0.12786(6) 0.0127(2) Uani 1 1 d . . . . .
N1 N 0.44124(10) 0.79859(16) 0.20947(5) 0.0147(2) Uani 1 1 d . . . . .
C1 C 0.33647(11) 0.75416(16) 0.26274(6) 0.0113(2) Uani 1 1 d . . . . .
H1 H 0.5285(17) 0.775(2) 0.2197(9) 0.022(4) Uiso 1 1 d . . . . .
H4B H 0.441(2) 0.358(3) 0.0987(10) 0.035(5) Uiso 1 1 d . . . . .
H2C H 0.4586(16) 0.944(2) 0.1067(10) 0.025(4) Uiso 1 1 d . . . . .
H2A H 0.3130(18) 0.881(2) 0.1253(10) 0.025(4) Uiso 1 1 d . . . . .
H2B H 0.4073(17) 0.722(3) 0.0959(10) 0.025(4) Uiso 1 1 d . . . . .
H4A H 0.3744(18) 0.393(3) 0.0267(12) 0.036(5) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H4B O4 H4A 106.6(16) . . ?
O2 N4 O3 120.46(9) . . ?
O2 N4 N3 125.84(9) . . ?
O3 N4 N3 113.70(9) . . ?
N4 N3 C1 118.49(9) . . ?
N1 N2 H2C 109.6(10) . . ?
N1 N2 H2A 110.9(10) . . ?
H2C N2 H2A 110.5(14) . . ?
N1 N2 H2B 110.9(10) . . ?
H2C N2 H2B 109.6(14) . . ?
H2A N2 H2B 105.3(14) . . ?
C1 N1 N2 116.64(9) . . ?
C1 N1 H1 123.5(10) . . ?
N2 N1 H1 118.4(10) . . ?
O1 C1 N1 120.46(10) . . ?
O1 C1 N3 131.56(10) . . ?
N1 C1 N3 107.98(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N4 1.2451(12) . ?
O4 H4B 0.872(19) . ?
O4 H4A 0.822(19) . ?
O1 C1 1.2275(13) . ?
O3 N4 1.2575(12) . ?
N4 N3 1.3270(12) . ?
N3 C1 1.3898(13) . ?
N2 N1 1.4128(13) . ?
N2 H2C 0.914(16) . ?
N2 H2A 0.884(17) . ?
N2 H2B 0.925(17) . ?
N1 C1 1.3559(13) . ?
N1 H1 0.864(16) . ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.864(16) 2.528(15) 3.0212(12) 117.1(12) 6_656
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N4 N3 C1 -4.49(15) . . . . ?
O3 N4 N3 C1 175.46(9) . . . . ?
N2 N1 C1 O1 -2.59(15) . . . . ?
N2 N1 C1 N3 177.47(9) . . . . ?
N4 N3 C1 O1 -1.54(17) . . . . ?
N4 N3 C1 N1 178.39(9) . . . . ?
