#------------------------------------------------------------------------------
#$Date: 2021-02-04 02:53:14 +0200 (Thu, 04 Feb 2021) $
#$Revision: 261473 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/56/4135604.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_4135604
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 N5 O3, C H6 N3'
_chemical_formula_sum            'C2 H6 N8 O3'
_chemical_formula_weight         190.15
_chemical_name_common            'guanidinium nitro-carbonyl-azide'
_chemical_name_systematic        'guanidinium nitro-carbonyl-azide'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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   difmap
_atom_sites_solution_primary     difmap
_audit_creation_date             2020-08-18
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 94.328(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4975(9)
_cell_length_b                   15.4884(16)
_cell_length_c                   6.6145(8)
_cell_measurement_reflns_used    1179
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.7900
_cell_measurement_theta_min      2.6370
_cell_volume                     765.91(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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      113(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -89.00  37.00   1.00   40.00    --  -23.84   0.00  90.00  126
  2  ω    -95.00 -63.00   1.00   40.00    --  -23.84 178.00 -90.00   32
  3  ω    -20.00  41.00   1.00   40.00    --  -23.84  37.00 120.00   61
  4  ω    -93.00 -62.00   1.00   40.00    --  -23.84 178.00  90.00   31
  5  ω    -95.00 -69.00   1.00   40.00    --  -23.84-178.00   0.00   26
  6  ω    -80.00 -46.00   1.00   40.00    --  -23.84 131.00  36.24   34
  7  ω    -31.00  -5.00   1.00   40.00    --   24.63 128.00  99.98   26
  8  ω    -31.00  -5.00   1.00   40.00    --   24.63 132.00-143.63   26
  9  ω    -17.00  54.00   1.00   40.00    --   24.63 -99.00 -60.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0927128000
_diffrn_orient_matrix_UB_12      0.0087205000
_diffrn_orient_matrix_UB_13      0.0021833000
_diffrn_orient_matrix_UB_21      0.0194720000
_diffrn_orient_matrix_UB_22      0.0441846000
_diffrn_orient_matrix_UB_23      0.0195121000
_diffrn_orient_matrix_UB_31      -0.0056057000
_diffrn_orient_matrix_UB_32      0.0083104000
_diffrn_orient_matrix_UB_33      -0.1057002000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0667
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6154
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.630
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0379
_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)+(0.0397P)²+0.0669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1234
_reflns_number_total             1564
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c12507_si_001.cif
_cod_data_source_block           px298
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4135604
_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   0.919
_shelx_estimated_absorpt_t_max   0.974
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.46529(15) 0.52534(8) 0.25893(17) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.22630(17) 0.43041(8) 0.04983(18) 0.0296(3) Uani 1 1 d . . . . .
O3 O 0.28092(17) 0.29322(8) 0.05350(19) 0.0327(3) Uani 1 1 d . . . . .
N7 N 0.3564(2) 0.70423(11) 0.2580(2) 0.0220(3) Uani 1 1 d . . . . .
N6 N 0.1314(2) 0.61396(11) 0.1339(2) 0.0233(4) Uani 1 1 d . . . . .
N1 N 0.72787(19) 0.44815(9) 0.3321(2) 0.0218(4) Uani 1 1 d . . . . .
N4 N 0.49328(18) 0.37655(9) 0.18639(19) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.78460(19) 0.51824(10) 0.4087(2) 0.0224(3) Uani 1 1 d . . . . .
N5 N 0.32749(19) 0.36848(9) 0.09512(19) 0.0218(3) Uani 1 1 d . . . . .
N8 N 0.0823(2) 0.76032(11) 0.1480(2) 0.0218(3) Uani 1 1 d . . . . .
N3 N 0.8449(2) 0.57818(11) 0.4795(2) 0.0321(4) Uani 1 1 d . . . . .
C2 C 0.1915(2) 0.69300(11) 0.1791(2) 0.0175(4) Uani 1 1 d . . . . .
C1 C 0.5446(2) 0.45660(11) 0.2529(2) 0.0186(4) Uani 1 1 d . . . . .
H8A H -0.020(3) 0.7516(13) 0.084(3) 0.034(6) Uiso 1 1 d . . . . .
H7A H 0.426(3) 0.6608(15) 0.278(3) 0.038(6) Uiso 1 1 d . . . . .
H7B H 0.406(3) 0.7573(15) 0.281(3) 0.036(6) Uiso 1 1 d . . . . .
H6A H 0.022(3) 0.6080(15) 0.076(3) 0.043(6) Uiso 1 1 d . . . . .
H8B H 0.124(3) 0.8123(15) 0.165(3) 0.039(6) Uiso 1 1 d . . . . .
H6B H 0.207(3) 0.5686(15) 0.144(3) 0.043(6) 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
C2 N7 H7A 120.3(15) . . ?
C2 N7 H7B 122.8(14) . . ?
H7A N7 H7B 117(2) . . ?
C2 N6 H6A 118.7(15) . . ?
C2 N6 H6B 120.1(14) . . ?
H6A N6 H6B 120(2) . . ?
N2 N1 C1 110.64(14) . . ?
N5 N4 C1 117.30(14) . . ?
N3 N2 N1 175.73(17) . . ?
O3 N5 O2 120.91(14) . . ?
O3 N5 N4 114.92(14) . . ?
O2 N5 N4 124.16(14) . . ?
C2 N8 H8A 118.0(14) . . ?
C2 N8 H8B 119.5(15) . . ?
H8A N8 H8B 121(2) . . ?
N7 C2 N6 120.16(17) . . ?
N7 C2 N8 120.36(17) . . ?
N6 C2 N8 119.46(17) . . ?
O1 C1 N4 132.66(16) . . ?
O1 C1 N1 121.41(15) . . ?
N4 C1 N1 105.90(14) . . ?
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
O1 C1 1.222(2) . ?
O2 N5 1.2454(18) . ?
O3 N5 1.2417(18) . ?
N7 C2 1.317(2) . ?
N7 H7A 0.86(2) . ?
N7 H7B 0.91(2) . ?
N6 C2 1.331(2) . ?
N6 H6A 0.89(2) . ?
N6 H6B 0.90(2) . ?
N1 N2 1.2583(19) . ?
N1 C1 1.439(2) . ?
N4 N5 1.3461(19) . ?
N4 C1 1.361(2) . ?
N2 N3 1.120(2) . ?
N8 C2 1.332(2) . ?
N8 H8A 0.86(2) . ?
N8 H8B 0.87(2) . ?
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
? ? ? ? ? ? ? ?
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
C1 N4 N5 O3 -173.84(13) . . . . ?
C1 N4 N5 O2 7.6(2) . . . . ?
N5 N4 C1 O1 5.4(3) . . . . ?
N5 N4 C1 N1 -176.73(12) . . . . ?
N2 N1 C1 O1 2.0(2) . . . . ?
N2 N1 C1 N4 -176.13(12) . . . . ?
