#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/14/4021470.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_4021470
loop_
_publ_author_name
'Konstantin Karaghiosoff'
'Thomas M. Klapötke'
'Peter Mayer'
'Holger Piotrowski'
'Kurt Polborn'
'Rodney L. Willer'
'Jan J. Weigand'
_publ_contact_author_address
;
Department Chemie
Ludwig-Maximilians Universität
Butenandtstrasse 5-13 (Haus D)
D-81377 München
Bundesrepublik Deutschland
;
_publ_contact_author_email       tmk@cup.uni-muenchen.de
_publ_contact_author_fax         +49-89-2180-77492
_publ_contact_author_name        'Thomas M. Klapötke '
_publ_contact_author_phone       +49-89-2180-77491
_publ_section_title
;
 N-Nitroso- and N-Nitraminotetrazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1295
_journal_page_last               1305
_journal_paper_doi               10.1021/jo0513820
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C3 H6 N6 O'
_chemical_formula_sum            'C3 H6 N6 O'
_chemical_formula_weight         142.14
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.285(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.045(2)
_cell_length_b                   5.7882(18)
_cell_length_c                   8.231(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      9
_cell_volume                     653.8(3)
_computing_cell_refinement       'CAD-4 Operations Manual'
_computing_data_collection       'CAD-4 Operations Manual (Nonius, 1994)'
_computing_data_reduction        'OpenMoleN (Nonius, 1997)'
_computing_molecular_graphics    ZORTEP(Zsolnai,Huttner,_1994)
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Nonius_MACH3
_diffrn_measurement_method       ο-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1107
_diffrn_reflns_theta_full        23.96
_diffrn_reflns_theta_max         23.96
_diffrn_reflns_theta_min         2.97
_diffrn_standards_decay_%        1.3
_diffrn_standards_interval_time  7200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9963
_exptl_absorpt_correction_T_min  0.8729
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   OpenMolEN(Nonius,1997)
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0630P)²+0.2299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                823
_reflns_number_total             1023
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0513820rom20050704_033027.cif
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4021470
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.88339(14) 0.2517(4) -0.0027(3) 0.0958(7) Uani 1 1 d .
N1 N 0.65365(12) 0.0342(3) 0.17813(18) 0.0486(5) Uani 1 1 d .
N2 N 0.59943(14) -0.0927(4) 0.2634(2) 0.0651(6) Uani 1 1 d .
N3 N 0.65494(17) -0.2561(4) 0.3344(2) 0.0735(6) Uani 1 1 d .
N4 N 0.74515(14) -0.2436(3) 0.2995(2) 0.0666(6) Uani 1 1 d .
N5 N 0.82029(12) 0.0061(3) 0.1383(2) 0.0510(5) Uani 1 1 d .
N6 N 0.81026(15) 0.1999(4) 0.0483(3) 0.0726(6) Uani 1 1 d .
C1 C 0.74127(14) -0.0630(4) 0.2023(2) 0.0462(5) Uani 1 1 d .
C2 C 0.60769(17) 0.2264(4) 0.0774(3) 0.0666(7) Uani 1 1 d .
H2A H 0.5431 0.2488 0.0957 0.080 Uiso 1 1 calc R
H2B H 0.6043 0.1932 -0.0380 0.080 Uiso 1 1 calc R
H2C H 0.6453 0.3641 0.1079 0.080 Uiso 1 1 calc R
C3 C 0.90829(17) -0.1316(5) 0.1689(3) 0.0790(8) Uani 1 1 d .
H3A H 0.8922 -0.2902 0.1842 0.095 Uiso 1 1 calc R
H3B H 0.9520 -0.0766 0.2672 0.095 Uiso 1 1 calc R
H3C H 0.9391 -0.1195 0.0757 0.095 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0831(12) 0.1042(15) 0.1103(15) 0.0306(12) 0.0436(11) -0.0154(11)
N1 0.0594(10) 0.0512(10) 0.0378(8) -0.0023(7) 0.0161(7) -0.0044(8)
N2 0.0737(12) 0.0752(13) 0.0514(10) -0.0001(10) 0.0248(9) -0.0163(11)
N3 0.0864(14) 0.0757(14) 0.0607(12) 0.0131(10) 0.0210(10) -0.0207(12)
N4 0.0760(13) 0.0619(12) 0.0589(11) 0.0169(9) 0.0077(9) -0.0083(10)
N5 0.0540(10) 0.0532(10) 0.0454(9) 0.0019(8) 0.0100(7) -0.0040(8)
N6 0.0732(13) 0.0705(13) 0.0790(13) 0.0204(11) 0.0274(11) -0.0045(10)
C1 0.0550(11) 0.0466(11) 0.0362(9) -0.0013(8) 0.0079(8) -0.0062(9)
C2 0.0673(14) 0.0651(15) 0.0713(15) 0.0084(12) 0.0233(11) 0.0147(12)
C3 0.0606(14) 0.0863(19) 0.0899(17) 0.0105(15) 0.0152(12) 0.0103(13)
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 N2 107.30(17)
C1 N1 C2 133.92(17)
N2 N1 C2 118.66(18)
N3 N2 N1 106.32(18)
N2 N3 N4 111.55(18)
C1 N4 N3 104.60(18)
N6 N5 C1 117.07(17)
N6 N5 C3 123.03(19)
C1 N5 C3 119.89(18)
O1 N6 N5 113.5(2)
N4 C1 N1 110.24(17)
N4 C1 N5 122.00(19)
N1 C1 N5 127.76(18)
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N5 C3 H3A 109.5
N5 C3 H3B 109.5
H3A C3 H3B 109.5
N5 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N6 1.227(2)
N1 C1 1.329(3)
N1 N2 1.356(2)
N1 C2 1.454(3)
N2 N3 1.284(3)
N3 N4 1.360(3)
N4 C1 1.310(3)
N5 N6 1.335(3)
N5 C1 1.385(2)
N5 C3 1.447(3)
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
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
C1 N1 N2 N3 0.3(2)
C2 N1 N2 N3 176.86(18)
N1 N2 N3 N4 -0.1(2)
N2 N3 N4 C1 -0.2(3)
C1 N5 N6 O1 179.2(2)
C3 N5 N6 O1 -1.4(3)
N3 N4 C1 N1 0.4(2)
N3 N4 C1 N5 -179.45(18)
N2 N1 C1 N4 -0.4(2)
C2 N1 C1 N4 -176.3(2)
N2 N1 C1 N5 179.39(17)
C2 N1 C1 N5 3.6(4)
N6 N5 C1 N4 -176.34(18)
C3 N5 C1 N4 4.2(3)
N6 N5 C1 N1 3.8(3)
C3 N5 C1 N1 -175.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 250947
2 PubChem 284757
