#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/50/4035069.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_4035069
loop_
_publ_author_name
'Klapötke, Thomas M'
'Krumm, Burkhard'
'Reith, Thomas'
'Unger, Cornelia C.'
_publ_section_title
;
 Synthetic Routes to a Triazole and Tetrazole with Trinitroalkyl
 Substitution at Nitrogen.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10505
_journal_page_last               10509
_journal_paper_doi               10.1021/acs.joc.8b01072
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C4 H5 N7 O6'
_chemical_formula_sum            'C4 H5 N7 O6'
_chemical_formula_weight         247.15
_chemical_name_common            1-(3,3,3-trinitropropyl)-tetrazole
_chemical_name_systematic        1-(3,3,3-trinitropropyl)-1H-tetrazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date
;
'Fri Aug 25 10:03:15 2017'
;
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 114.457(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0691(16)
_cell_length_b                   7.7257(9)
_cell_length_c                   12.030(2)
_cell_measurement_reflns_used    1489
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      27.2120
_cell_measurement_theta_min      4.3420
_cell_volume                     936.5(3)
_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
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      143(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6171
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.336
_diffrn_reflns_theta_min         4.199
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08373
_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.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0449
_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)+(0.0254P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1463
_reflns_number_total             2197
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b01072_si_003.cif
_cod_data_source_block           manuscript
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035069
_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.
;
_shelxl_version_number           2013-4
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
N5 N 0.19148(15) 0.7448(2) 0.77792(14) 0.0222(4) Uani 1 1 d
O5 O 0.02669(12) 0.8302(2) 0.96609(13) 0.0348(4) Uani 1 1 d
N6 N 0.21629(16) 0.5563(2) 0.94892(14) 0.0245(4) Uani 1 1 d
O1 O 0.19201(13) 0.88769(19) 0.73551(11) 0.0286(4) Uani 1 1 d
O6 O -0.03807(12) 0.7508(2) 0.77715(12) 0.0340(4) Uani 1 1 d
N1 N 0.35574(13) 1.1461(2) 1.08504(13) 0.0183(4) Uani 1 1 d
N2 N 0.48522(15) 1.1765(2) 1.11659(15) 0.0268(4) Uani 1 1 d
N7 N 0.04597(15) 0.7790(2) 0.87976(15) 0.0220(4) Uani 1 1 d
O2 O 0.18934(14) 0.6060(2) 0.72988(13) 0.0342(4) Uani 1 1 d
N3 N 0.52810(15) 1.2559(2) 1.22028(15) 0.0309(4) Uani 1 1 d
O3 O 0.33039(14) 0.50833(19) 0.98212(15) 0.0423(4) Uani 1 1 d
O4 O 0.12355(13) 0.47272(19) 0.94893(13) 0.0347(4) Uani 1 1 d
N4 N 0.42952(16) 1.2791(2) 1.25828(15) 0.0316(4) Uani 1 1 d
C2 C 0.2749(2) 1.0554(3) 0.97183(18) 0.0243(5) Uani 1 1 d
C3 C 0.28906(19) 0.8609(3) 0.99709(17) 0.0176(4) Uani 1 1 d
C1 C 0.3246(2) 1.2100(3) 1.17221(18) 0.0262(5) Uani 1 1 d
C4 C 0.19037(17) 0.7443(2) 0.90397(16) 0.0170(4) Uani 1 1 d
H4 H 0.2800(16) 0.834(3) 1.0687(17) 0.020(5) Uiso 1 1 d
H5 H 0.3705(19) 0.824(3) 1.0038(16) 0.025(5) Uiso 1 1 d
H2 H 0.1862(18) 1.091(3) 0.9490(16) 0.025(5) Uiso 1 1 d
H3 H 0.3072(18) 1.091(3) 0.9133(18) 0.031(6) Uiso 1 1 d
H1 H 0.241(2) 1.203(3) 1.1683(18) 0.038(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
O2 N5 O1 127.17(17)
O2 N5 C4 117.76(16)
O1 N5 C4 115.05(16)
O4 N6 O3 127.04(18)
O4 N6 C4 117.98(15)
O3 N6 C4 114.97(16)
C1 N1 N2 107.92(15)
C1 N1 C2 130.93(17)
N2 N1 C2 121.15(16)
N3 N2 N1 106.17(15)
O5 N7 O6 126.57(16)
O5 N7 C4 115.90(14)
O6 N7 C4 117.52(16)
N2 N3 N4 111.25(15)
C1 N4 N3 104.71(16)
N1 C2 C3 108.26(15)
N1 C2 H2 107.0(12)
C3 C2 H2 110.7(13)
N1 C2 H3 106.2(13)
C3 C2 H3 113.0(13)
H2 C2 H3 111.4(16)
C4 C3 C2 117.34(16)
C4 C3 H4 103.3(11)
C2 C3 H4 111.4(12)
C4 C3 H5 105.3(12)
C2 C3 H5 110.0(13)
H4 C3 H5 109.0(16)
N4 C1 N1 109.95(18)
N4 C1 H1 128.1(13)
N1 C1 H1 122.0(14)
C3 C4 N5 116.05(15)
C3 C4 N7 114.76(16)
N5 C4 N7 104.44(13)
C3 C4 N6 109.48(14)
N5 C4 N6 106.03(14)
N7 C4 N6 105.19(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N5 O2 1.213(2)
N5 O1 1.217(2)
N5 C4 1.522(2)
O5 N7 1.2101(19)
N6 O4 1.2130(19)
N6 O3 1.2142(19)
N6 C4 1.535(2)
O6 N7 1.2189(19)
N1 C1 1.327(2)
N1 N2 1.343(2)
N1 C2 1.462(2)
N2 N3 1.291(2)
N7 C4 1.525(2)
N3 N4 1.358(2)
N4 C1 1.308(3)
C2 C3 1.528(3)
C2 H2 0.944(18)
C2 H3 0.95(2)
C3 C4 1.499(3)
C3 H4 0.932(19)
C3 H5 0.918(19)
C1 H1 0.91(2)
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 0.2(2)
C2 N1 N2 N3 -179.31(17)
N1 N2 N3 N4 -0.1(2)
N2 N3 N4 C1 -0.2(2)
C1 N1 C2 C3 -93.4(2)
N2 N1 C2 C3 86.0(2)
N1 C2 C3 C4 165.34(16)
N3 N4 C1 N1 0.3(2)
N2 N1 C1 N4 -0.3(2)
C2 N1 C1 N4 179.14(19)
C2 C3 C4 N5 63.2(2)
C2 C3 C4 N7 -58.9(2)
C2 C3 C4 N6 -176.87(17)
O2 N5 C4 C3 133.47(18)
O1 N5 C4 C3 -47.8(2)
O2 N5 C4 N7 -99.13(18)
O1 N5 C4 N7 79.57(18)
O2 N5 C4 N6 11.7(2)
O1 N5 C4 N6 -169.60(14)
O5 N7 C4 C3 -32.6(2)
O6 N7 C4 C3 148.32(17)
O5 N7 C4 N5 -160.81(16)
O6 N7 C4 N5 20.1(2)
O5 N7 C4 N6 87.76(18)
O6 N7 C4 N6 -91.30(18)
O4 N6 C4 C3 128.53(17)
O3 N6 C4 C3 -50.8(2)
O4 N6 C4 N5 -105.58(17)
O3 N6 C4 N5 75.08(18)
O4 N6 C4 N7 4.7(2)
O3 N6 C4 N7 -174.63(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328876
