#------------------------------------------------------------------------------
#$Date: 2021-02-04 02:53:14 +0200 (Thu, 04 Feb 2021) $
#$Revision: 261473 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/56/4135608.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_4135608
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         'C2 H4 N2 O4'
_chemical_formula_sum            'C2 H4 N2 O4'
_chemical_formula_weight         120.07
_chemical_name_common            'methyl nitrocarbamate'
_chemical_name_systematic        'methyl nitrocarbamate'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     difmap
_audit_creation_date             2020-09-03
_audit_creation_method           SHELXL-2018/3
_audit_update_record             2020-10-01
_cell_angle_alpha                99.142(12)
_cell_angle_beta                 90.045(12)
_cell_angle_gamma                103.622(12)
_cell_formula_units_Z            4
_cell_length_a                   7.6411(10)
_cell_length_b                   7.7969(11)
_cell_length_c                   8.3332(13)
_cell_measurement_reflns_used    801
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.4310
_cell_measurement_theta_min      2.5600
_cell_volume                     475.99(12)
_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      110(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -41.00  52.00   1.00   47.00    --   29.64 -57.00  30.00   93
  2  ω    -19.00  72.00   1.00   47.00    --   29.64 -99.00 -90.00   91
  3  ω      6.00  99.00   1.00   47.00    --   29.64  57.00-180.00   93
  4  ω     81.00 112.00   1.00   47.00    --   29.64-178.00 120.00   31
  5  ω    -44.00  45.00   1.00   47.00    --   29.64 -37.00 -90.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0533045000
_diffrn_orient_matrix_UB_12      0.0519306000
_diffrn_orient_matrix_UB_13      -0.0302058000
_diffrn_orient_matrix_UB_21      -0.0059700000
_diffrn_orient_matrix_UB_22      0.0445931000
_diffrn_orient_matrix_UB_23      0.0801806000
_diffrn_orient_matrix_UB_31      0.0791227000
_diffrn_orient_matrix_UB_32      0.0657092000
_diffrn_orient_matrix_UB_33      -0.0101498000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3157
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.358
_diffrn_reflns_theta_min         2.725
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57409
_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    1.676
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0489
_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)+(0.0888P)²+0.0051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1484
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1449
_reflns_number_total             1947
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c12507_si_001.cif
_cod_data_source_block           px309
_cod_database_code               4135608
_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   0.960
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O6 O 0.80598(17) 0.98936(18) 0.29462(16) 0.0284(4) Uani 1 1 d . . . . .
O5 O 0.58500(17) 0.81415(18) 0.41616(18) 0.0313(4) Uani 1 1 d . . . . .
O1 O 0.91431(17) 0.63164(19) 0.41624(17) 0.0326(4) Uani 1 1 d . . . . .
O2 O 0.69642(18) 0.38436(19) 0.32622(16) 0.0316(4) Uani 1 1 d . . . . .
O7 O 0.60134(18) 0.9359(2) 0.73502(17) 0.0360(4) Uani 1 1 d . . . . .
O4 O 0.6603(2) 0.5523(2) 0.84147(18) 0.0396(4) Uani 1 1 d . . . . .
O3 O 0.87663(19) 0.7302(2) 0.73581(19) 0.0391(4) Uani 1 1 d . . . . .
O8 O 0.8132(2) 1.1735(2) 0.81397(19) 0.0431(4) Uani 1 1 d . . . . .
C1 C 0.7863(2) 0.5149(2) 0.4367(2) 0.0226(4) Uani 1 1 d . . . . .
C3 C 0.7122(2) 0.9393(2) 0.4194(2) 0.0225(4) Uani 1 1 d . . . . .
C4 C 0.7485(4) 0.8795(4) 0.1373(3) 0.0373(6) Uani 1 1 d . . . . .
C2 C 0.7564(4) 0.3779(4) 0.1613(3) 0.0390(6) Uani 1 1 d . . . . .
N2 N 0.7519(2) 0.5995(2) 0.7284(2) 0.0278(4) Uani 1 1 d . . . . .
N4 N 0.7285(2) 1.0531(2) 0.7111(2) 0.0266(4) Uani 1 1 d . . . . .
N1 N 0.7025(2) 0.4902(2) 0.58181(19) 0.0248(4) Uani 1 1 d . . . . .
N3 N 0.7901(2) 1.0581(2) 0.55543(19) 0.0246(4) Uani 1 1 d . . . . .
H4C H 0.823(4) 0.942(4) 0.064(4) 0.073(9) Uiso 1 1 d . . . . .
H4B H 0.767(5) 0.764(5) 0.125(4) 0.093(12) Uiso 1 1 d . . . . .
H4A H 0.637(5) 0.877(4) 0.102(4) 0.082(10) Uiso 1 1 d . . . . .
H1 H 0.612(3) 0.413(3) 0.593(3) 0.033(6) Uiso 1 1 d . . . . .
H3 H 0.878(3) 1.144(3) 0.552(3) 0.034(6) Uiso 1 1 d . . . . .
H2A H 0.673(5) 0.284(5) 0.095(4) 0.098(12) Uiso 1 1 d . . . . .
H2C H 0.737(5) 0.466(5) 0.114(4) 0.092(12) Uiso 1 1 d . . . . .
H2B H 0.869(5) 0.381(5) 0.147(4) 0.107(13) 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
C3 O6 C4 115.94(16) . . ?
C1 O2 C2 117.36(16) . . ?
O1 C1 O2 127.14(18) . . ?
O1 C1 N1 127.14(19) . . ?
O2 C1 N1 105.73(14) . . ?
O5 C3 O6 127.01(18) . . ?
O5 C3 N3 126.45(18) . . ?
O6 C3 N3 106.54(15) . . ?
O6 C4 H4C 103(2) . . ?
O6 C4 H4B 116(2) . . ?
H4C C4 H4B 108(3) . . ?
O6 C4 H4A 115(2) . . ?
H4C C4 H4A 103(3) . . ?
H4B C4 H4A 111(3) . . ?
O2 C2 H2A 108(2) . . ?
O2 C2 H2C 113(2) . . ?
H2A C2 H2C 97(3) . . ?
O2 C2 H2B 117(2) . . ?
H2A C2 H2B 116(3) . . ?
H2C C2 H2B 104(3) . . ?
O3 N2 O4 126.39(18) . . ?
O3 N2 N1 119.33(16) . . ?
O4 N2 N1 114.28(16) . . ?
O7 N4 O8 125.96(17) . . ?
O7 N4 N3 119.85(17) . . ?
O8 N4 N3 114.18(15) . . ?
N2 N1 C1 124.99(15) . . ?
N2 N1 H1 108.9(16) . . ?
C1 N1 H1 126.0(16) . . ?
C3 N3 N4 124.38(15) . . ?
C3 N3 H3 123.3(16) . . ?
N4 N3 H3 112.2(16) . . ?
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
O6 C3 1.321(2) . ?
O6 C4 1.452(3) . ?
O5 C3 1.201(2) . ?
O1 C1 1.202(2) . ?
O2 C1 1.314(2) . ?
O2 C2 1.446(3) . ?
O7 N4 1.208(2) . ?
O4 N2 1.226(2) . ?
O3 N2 1.214(2) . ?
O8 N4 1.221(2) . ?
C1 N1 1.388(2) . ?
C3 N3 1.379(3) . ?
C4 H4C 0.95(3) . ?
C4 H4B 0.93(4) . ?
C4 H4A 0.90(3) . ?
C2 H2A 0.95(4) . ?
C2 H2C 0.88(4) . ?
C2 H2B 0.86(4) . ?
N2 N1 1.371(2) . ?
N4 N3 1.384(2) . ?
N1 H1 0.82(2) . ?
N3 H3 0.83(3) . ?
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
C2 O2 C1 O1 0.2(3) . . . . ?
C2 O2 C1 N1 -179.92(17) . . . . ?
C4 O6 C3 O5 -0.5(3) . . . . ?
C4 O6 C3 N3 178.97(17) . . . . ?
O3 N2 N1 C1 0.9(3) . . . . ?
O4 N2 N1 C1 -179.51(17) . . . . ?
O1 C1 N1 N2 1.1(3) . . . . ?
O2 C1 N1 N2 -178.78(16) . . . . ?
O5 C3 N3 N4 -1.8(3) . . . . ?
O6 C3 N3 N4 178.69(16) . . . . ?
O7 N4 N3 C3 2.2(3) . . . . ?
O8 N4 N3 C3 -177.98(18) . . . . ?
