#------------------------------------------------------------------------------
#$Date: 2023-11-10 21:21:08 +0200 (Fri, 10 Nov 2023) $
#$Revision: 287519 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/56/7215633.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_7215633
loop_
_publ_author_name
'Klapötke, Thomas M.'
'Miró Sabaté, Carles'
'Rasp, Matthias'
_publ_section_title
;
 Synthesis and properties of 5-nitrotetrazole derivatives as new energetic
 materials
;
_journal_issue                   15
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              2240
_journal_paper_doi               10.1039/b818925k
_journal_volume                  19
_journal_year                    2009
_chemical_formula_moiety         'C3 H2 N6 O2'
_chemical_formula_sum            'C3 H2 N6 O2'
_chemical_formula_weight         154.11
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2008-09-01T14:27:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4521(3)
_cell_length_b                   6.1470(3)
_cell_length_c                   17.4832(9)
_cell_measurement_reflns_used    4260
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.9987
_cell_measurement_theta_min      3.7342
_cell_volume                     585.93(5)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Oxford Xcalibur3 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7761
_diffrn_reflns_theta_full        30.10
_diffrn_reflns_theta_max         30.10
_diffrn_reflns_theta_min         3.91
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0255
_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/[σ²(Fo²)+(0.0338P)²+0.4333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0563
_refine_ls_wR_factor_ref         0.0622
_reflns_number_gt                896
_reflns_number_total             1036
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b818925k.txt
_cod_data_source_block           dx098-NTAN
_cod_database_code               7215633
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
O2 O -0.0748(2) 0.04824(19) 0.34568(6) 0.0199(2) Uani 1 1 d
O1 O 0.2311(2) -0.13448(19) 0.39350(6) 0.0215(3) Uani 1 1 d
N5 N 0.1358(2) 0.0344(2) 0.20515(7) 0.0120(2) Uani 1 1 d
N4 N 0.3019(2) -0.02001(19) 0.15331(7) 0.0120(2) Uani 1 1 d
N1 N 0.1214(2) -0.0466(2) 0.34082(7) 0.0143(2) Uani 1 1 d
N2 N 0.4455(2) -0.1631(2) 0.25364(7) 0.0148(3) Uani 1 1 d
N3 N 0.4883(2) -0.1377(2) 0.17999(7) 0.0152(3) Uani 1 1 d
N6 N -0.1314(3) -0.0745(2) 0.01441(8) 0.0208(3) Uani 1 1 d
C2 C 0.2869(3) 0.0470(3) 0.07310(8) 0.0147(3) Uani 1 1 d
C3 C 0.0524(3) -0.0251(3) 0.03997(8) 0.0149(3) Uani 1 1 d
C1 C 0.2341(3) -0.0586(2) 0.26587(8) 0.0122(3) Uani 1 1 d
H1 H 0.426(3) -0.020(3) 0.0466(9) 0.013(4) Uiso 1 1 d
H2 H 0.296(4) 0.211(3) 0.0706(11) 0.028(5) Uiso 1 1 d
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
O2 0.0195(6) 0.0205(5) 0.0197(5) 0.0004(5) 0.0038(5) 0.0042(5)
O1 0.0277(6) 0.0234(5) 0.0133(5) 0.0056(5) -0.0056(5) -0.0004(6)
N5 0.0123(6) 0.0113(5) 0.0125(5) -0.0010(5) -0.0001(4) -0.0018(5)
N4 0.0115(5) 0.0115(5) 0.0129(5) -0.0006(5) 0.0000(5) -0.0002(5)
N1 0.0184(6) 0.0111(5) 0.0135(5) -0.0001(5) -0.0011(5) -0.0022(5)
N2 0.0154(6) 0.0128(6) 0.0162(6) 0.0005(5) -0.0013(5) 0.0000(5)
N3 0.0151(6) 0.0133(5) 0.0172(6) -0.0004(5) -0.0011(5) 0.0018(5)
N6 0.0191(7) 0.0242(7) 0.0190(6) -0.0010(6) -0.0010(5) 0.0001(6)
C2 0.0150(7) 0.0167(6) 0.0126(6) 0.0014(6) 0.0004(5) -0.0013(7)
C3 0.0182(7) 0.0145(7) 0.0120(6) -0.0004(6) 0.0005(6) 0.0019(6)
C1 0.0128(6) 0.0096(6) 0.0142(6) -0.0008(5) -0.0016(5) -0.0020(6)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N5 N4 99.43(12)
N5 N4 N3 114.79(11)
N5 N4 C2 123.11(12)
N3 N4 C2 122.08(12)
O2 N1 O1 125.89(13)
O2 N1 C1 117.30(12)
O1 N1 C1 116.81(12)
N3 N2 C1 104.62(12)
N2 N3 N4 105.74(12)
N4 C2 C3 109.92(12)
N4 C2 H1 107.0(10)
C3 C2 H1 111.0(10)
N4 C2 H2 108.6(11)
C3 C2 H2 109.1(11)
H1 C2 H2 111.1(15)
N6 C3 C2 177.90(17)
N5 C1 N2 115.43(13)
N5 C1 N1 122.25(13)
N2 C1 N1 122.32(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 N1 1.2211(16)
O1 N1 1.2239(16)
N5 C1 1.3192(18)
N5 N4 1.3242(16)
N4 N3 1.3318(16)
N4 C2 1.4640(19)
N1 C1 1.4489(18)
N2 N3 1.3178(18)
N2 C1 1.3367(19)
N6 C3 1.138(2)
C2 C3 1.472(2)
C2 H1 0.977(17)
C2 H2 1.007(19)
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 N5 N4 N3 0.06(15)
C1 N5 N4 C2 -178.64(13)
C1 N2 N3 N4 0.27(15)
N5 N4 N3 N2 -0.22(16)
C2 N4 N3 N2 178.50(13)
N5 N4 C2 C3 -56.50(17)
N3 N4 C2 C3 124.89(14)
N4 N5 C1 N2 0.12(16)
N4 N5 C1 N1 179.63(12)
N3 N2 C1 N5 -0.26(17)
N3 N2 C1 N1 -179.76(13)
O2 N1 C1 N5 2.2(2)
O1 N1 C1 N5 -178.37(13)
O2 N1 C1 N2 -178.29(13)
O1 N1 C1 N2 1.1(2)
_cod_duplicate_entry 7200616
