# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nmo
_database_code_depnum_ccdc_archive 'CCDC 2119618'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-11-01 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
3-(nitromethylene)oxetane
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H5 N O3'
_chemical_formula_sum            'C4 H5 N O3'
_chemical_formula_weight         115.09

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.5374(10)
_cell_length_b                   5.7930(3)
_cell_length_c                   13.2478(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.740(6)
_cell_angle_gamma                90
_cell_volume                     962.10(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1556
_cell_measurement_theta_min      4.4170
_cell_measurement_theta_max      31.6830

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82520
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            3509
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.162
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             984
_reflns_number_gt                896
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.5306P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         984
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.36535(8) 0.09445(16) 0.75307(7) 0.0251(3) Uani 1 1 d . . . . .
N1 N 0.38090(8) 0.37754(17) 0.45312(8) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.37023(10) -0.0695(2) 0.66954(9) 0.0226(3) Uani 1 1 d . . . . .
H1A H 0.305686 -0.166874 0.662440 0.027 Uiso 1 1 calc R U . . .
H1B H 0.435585 -0.165393 0.670264 0.027 Uiso 1 1 calc R U . . .
O2 O 0.38453(8) 0.39123(17) 0.36019(7) 0.0290(3) Uani 1 1 d . . . . .
C2 C 0.37043(10) 0.2896(2) 0.68309(9) 0.0209(3) Uani 1 1 d . . . . .
H2A H 0.435879 0.383734 0.691167 0.025 Uiso 1 1 calc R U . . .
H2B H 0.306008 0.388334 0.683586 0.025 Uiso 1 1 calc R U . . .
O3 O 0.37961(7) 0.54721(16) 0.50898(7) 0.0258(3) Uani 1 1 d . . . . .
C3 C 0.37372(10) 0.1271(2) 0.59561(10) 0.0188(3) Uani 1 1 d . . . . .
C4 C 0.37799(10) 0.1489(2) 0.49605(10) 0.0196(3) Uani 1 1 d . . . . .
H4 H 0.379104 0.016343 0.453840 0.024 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.4600(15) . ?
O1 C2 1.4637(15) . ?
N1 O3 1.2306(13) . ?
N1 O2 1.2352(14) . ?
N1 C4 1.4422(16) . ?
C1 C3 1.5031(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.4937(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.3268(18) . ?
C4 H4 0.9500 . ?

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
C1 O1 C2 91.12(9) . . ?
O3 N1 O2 123.30(11) . . ?
O3 N1 C4 119.73(10) . . ?
O2 N1 C4 116.97(10) . . ?
O1 C1 C3 90.16(10) . . ?
O1 C1 H1A 113.6 . . ?
C3 C1 H1A 113.6 . . ?
O1 C1 H1B 113.6 . . ?
C3 C1 H1B 113.6 . . ?
H1A C1 H1B 110.9 . . ?
O1 C2 C3 90.39(9) . . ?
O1 C2 H2A 113.6 . . ?
C3 C2 H2A 113.6 . . ?
O1 C2 H2B 113.6 . . ?
C3 C2 H2B 113.6 . . ?
H2A C2 H2B 110.8 . . ?
C4 C3 C2 135.51(12) . . ?
C4 C3 C1 136.19(12) . . ?
C2 C3 C1 88.31(10) . . ?
C3 C4 N1 118.73(11) . . ?
C3 C4 H4 120.6 . . ?
N1 C4 H4 120.6 . . ?

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 O1 C1 C3 -0.88(9) . . . . ?
C1 O1 C2 C3 0.89(9) . . . . ?
O1 C2 C3 C4 179.21(15) . . . . ?
O1 C2 C3 C1 -0.86(9) . . . . ?
O1 C1 C3 C4 -179.20(15) . . . . ?
O1 C1 C3 C2 0.87(9) . . . . ?
C2 C3 C4 N1 0.3(2) . . . . ?
C1 C3 C4 N1 -179.61(13) . . . . ?
O3 N1 C4 C3 0.14(18) . . . . ?
O2 N1 C4 C3 -179.79(11) . . . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.046

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ca5at
_database_code_depnum_ccdc_archive 'CCDC 2119619'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-11-01 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
2-(3-(nitromethyl)oxetan-3-yl)-2H-tetrazol-5-amine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H8 N6 O3'
_chemical_formula_sum            'C5 H8 N6 O3'
_chemical_formula_weight         200.17

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6779(6)
_cell_length_b                   9.9578(8)
_cell_length_c                   13.9118(13)
_cell_angle_alpha                103.269(8)
_cell_angle_beta                 101.444(8)
_cell_angle_gamma                104.382(7)
_cell_volume                     839.56(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1880
_cell_measurement_theta_min      1.7190
_cell_measurement_theta_max      28.5350

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96056
_exptl_absorpt_correction_T_max  1.00000
_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.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            5638
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.301
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3391
_reflns_number_gt                2650
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.1330P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3391
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.0578(2) 0.75780(12) 0.29795(9) 0.0240(3) Uani 1 1 d . . . . .
H1B H -0.211(3) 0.6189(18) 0.1544(12) 0.013(4) Uiso 1 1 d . . . . .
H1A H -0.263(3) 0.7728(17) 0.1729(12) 0.018(4) Uiso 1 1 d . . . . .
N1 N 0.2918(2) 1.00990(15) 0.13087(11) 0.0227(3) Uani 1 1 d . . . . .
C1 C -0.1509(3) 0.72633(19) 0.18860(14) 0.0213(4) Uani 1 1 d . . . . .
N2 N 0.1594(2) 0.57099(14) 0.14447(10) 0.0192(3) Uani 1 1 d . . . . .
H2B H 0.260(3) 0.8084(19) 0.3168(14) 0.023 Uiso 1 1 d . U . . .
H2A H 0.170(3) 0.945(2) 0.3234(13) 0.023 Uiso 1 1 d . U . . .
C2 C 0.1480(3) 0.8444(2) 0.29181(13) 0.0211(4) Uani 1 1 d . . . . .
O2 O 0.3180(2) 1.06432(13) 0.06229(10) 0.0305(3) Uani 1 1 d . . . . .
O3 O 0.4320(2) 1.02982(14) 0.20862(10) 0.0351(3) Uani 1 1 d . . . . .
N3 N 0.1634(2) 0.69654(14) 0.12255(10) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.0685(3) 0.80013(17) 0.17384(12) 0.0182(4) Uani 1 1 d . . . . .
O4 O 1.1193(2) 0.24204(12) 0.20591(9) 0.0269(3) Uani 1 1 d . . . . .
H4A H -0.001(3) 0.9821(18) 0.1536(13) 0.019(5) Uiso 1 1 d . . . . .
H4B H 0.002(3) 0.8783(18) 0.0484(14) 0.021(5) Uiso 1 1 d . . . . .
N4 N 0.2622(2) 0.71945(15) 0.05227(11) 0.0208(3) Uani 1 1 d . . . . .
C4 C 0.0700(3) 0.91710(18) 0.12081(14) 0.0208(4) Uani 1 1 d . . . . .
N8 N 0.8698(2) 0.09035(15) 0.35889(11) 0.0219(3) Uani 1 1 d . . . . .
H7B H 0.788(3) 0.1618(19) 0.1719(13) 0.020(5) Uiso 1 1 d . . . . .
H7A H 0.876(3) 0.3258(18) 0.1633(13) 0.019(4) Uiso 1 1 d . . . . .
C7 C 0.9055(3) 0.2567(2) 0.20076(14) 0.0238(4) Uani 1 1 d . . . . .
N9 N 0.8539(2) 0.22470(14) 0.36926(10) 0.0184(3) Uani 1 1 d . . . . .
C8 C 0.9656(3) 0.32042(17) 0.31801(13) 0.0188(4) Uani 1 1 d . . . . .
N7 N 0.7616(2) 0.50128(15) 0.35167(11) 0.0228(3) Uani 1 1 d . . . . .
H9B H 1.049(3) 0.5356(18) 0.3222(13) 0.019(4) Uiso 1 1 d . . . . .
H9A H 1.059(3) 0.5184(18) 0.4333(14) 0.021(5) Uiso 1 1 d . . . . .
C9 C 0.9769(3) 0.47724(18) 0.36133(14) 0.0201(4) Uani 1 1 d . . . . .
N10 N 0.7249(2) 0.25775(15) 0.42402(11) 0.0208(3) Uani 1 1 d . . . . .
N11 N 0.6489(2) 0.14226(15) 0.45405(11) 0.0215(3) Uani 1 1 d . . . . .
C10 C 0.7398(3) 0.04210(18) 0.41329(13) 0.0201(4) Uani 1 1 d . . . . .
N12 N 0.7003(3) -0.09108(18) 0.42675(14) 0.0326(4) Uani 1 1 d . . . . .
H121 H 0.771(4) -0.150(2) 0.3975(16) 0.039 Uiso 1 1 d . U . . .
H122 H 0.618(4) -0.112(2) 0.4626(16) 0.039 Uiso 1 1 d . U . . .
O6 O 0.6278(2) 0.44280(14) 0.26843(10) 0.0315(3) Uani 1 1 d . . . . .
H6B H 1.233(3) 0.2370(19) 0.3543(13) 0.023(5) Uiso 1 1 d . . . . .
H6A H 1.301(3) 0.399(2) 0.3355(14) 0.025(5) Uiso 1 1 d . . . . .
H61 H 0.403(4) 0.376(2) 0.0432(16) 0.042(6) Uiso 1 1 d . . . . .
H62 H 0.268(3) 0.3440(18) 0.1161(14) 0.021(5) Uiso 1 1 d . . . . .
N6 N 0.2910(3) 0.38277(15) 0.06583(12) 0.0201(3) Uani 1 1 d . . . . .
C6 C 1.1896(3) 0.3057(2) 0.31652(14) 0.0237(4) Uani 1 1 d . . . . .
O5 O 0.7345(2) 0.58154(13) 0.42575(10) 0.0306(3) Uani 1 1 d . . . . .
N5 N 0.3276(2) 0.60491(15) 0.02344(10) 0.0209(3) Uani 1 1 d . . . . .
C5 C 0.2630(3) 0.51622(17) 0.07995(12) 0.0177(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.452(2) . ?
O1 C2 1.460(2) . ?
N1 O2 1.2211(18) . ?
N1 O3 1.2220(19) . ?
N1 C4 1.499(2) . ?
C1 C3 1.544(2) . ?
C1 H1B 1.005(17) . ?
C1 H1A 0.985(17) . ?
N2 C5 1.338(2) . ?
N2 N3 1.3485(18) . ?
C2 C3 1.541(2) . ?
C2 H2B 0.948(18) . ?
C2 H2A 0.961(18) . ?
N3 N4 1.3141(18) . ?
N3 C3 1.463(2) . ?
C3 C4 1.514(2) . ?
O4 C6 1.452(2) . ?
O4 C7 1.460(2) . ?
N4 N5 1.3267(18) . ?
C4 H4A 0.975(17) . ?
C4 H4B 0.961(18) . ?
N8 C10 1.333(2) . ?
N8 N9 1.3454(18) . ?
C7 C8 1.537(2) . ?
C7 H7B 1.002(19) . ?
C7 H7A 0.989(17) . ?
N9 N10 1.3102(18) . ?
N9 C8 1.464(2) . ?
C8 C9 1.516(2) . ?
C8 C6 1.542(2) . ?
N7 O6 1.2249(19) . ?
N7 O5 1.2255(18) . ?
N7 C9 1.500(2) . ?
C9 H9B 0.989(18) . ?
C9 H9A 0.976(18) . ?
N10 N11 1.3302(19) . ?
N11 C10 1.365(2) . ?
C10 N12 1.350(2) . ?
N12 H121 0.92(2) . ?
N12 H122 0.84(2) . ?
N6 C5 1.363(2) . ?
N6 H61 0.88(2) . ?
N6 H62 0.894(19) . ?
C6 H6B 1.015(18) . ?
C6 H6A 0.972(19) . ?
N5 C5 1.360(2) . ?

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
C1 O1 C2 91.50(12) . . ?
O2 N1 O3 124.57(16) . . ?
O2 N1 C4 117.60(14) . . ?
O3 N1 C4 117.79(14) . . ?
O1 C1 C3 91.46(13) . . ?
O1 C1 H1B 111.1(9) . . ?
C3 C1 H1B 115.4(9) . . ?
O1 C1 H1A 113.0(9) . . ?
C3 C1 H1A 115.2(10) . . ?
H1B C1 H1A 109.6(14) . . ?
C5 N2 N3 100.70(12) . . ?
O1 C2 C3 91.26(13) . . ?
O1 C2 H2B 110.9(11) . . ?
C3 C2 H2B 114.0(11) . . ?
O1 C2 H2A 109.6(11) . . ?
C3 C2 H2A 112.9(10) . . ?
H2B C2 H2A 115.4(16) . . ?
N4 N3 N2 114.55(12) . . ?
N4 N3 C3 122.59(13) . . ?
N2 N3 C3 122.85(13) . . ?
N3 C3 C4 109.49(13) . . ?
N3 C3 C2 113.34(13) . . ?
C4 C3 C2 119.15(14) . . ?
N3 C3 C1 112.97(13) . . ?
C4 C3 C1 115.07(14) . . ?
C2 C3 C1 85.07(13) . . ?
C6 O4 C7 92.11(12) . . ?
N3 N4 N5 106.15(12) . . ?
N1 C4 C3 113.17(14) . . ?
N1 C4 H4A 106.1(10) . . ?
C3 C4 H4A 108.3(10) . . ?
N1 C4 H4B 105.7(11) . . ?
C3 C4 H4B 112.7(10) . . ?
H4A C4 H4B 110.7(14) . . ?
C10 N8 N9 100.96(13) . . ?
O4 C7 C8 90.94(13) . . ?
O4 C7 H7B 113.4(10) . . ?
C8 C7 H7B 115.1(10) . . ?
O4 C7 H7A 112.5(10) . . ?
C8 C7 H7A 113.5(10) . . ?
H7B C7 H7A 110.3(14) . . ?
N10 N9 N8 114.56(13) . . ?
N10 N9 C8 124.14(13) . . ?
N8 N9 C8 121.23(12) . . ?
N9 C8 C9 112.60(13) . . ?
N9 C8 C7 113.81(14) . . ?
C9 C8 C7 117.95(14) . . ?
N9 C8 C6 112.37(13) . . ?
C9 C8 C6 111.49(14) . . ?
C7 C8 C6 85.83(13) . . ?
O6 N7 O5 124.68(15) . . ?
O6 N7 C9 117.13(14) . . ?
O5 N7 C9 118.13(15) . . ?
N7 C9 C8 114.03(15) . . ?
N7 C9 H9B 105.5(10) . . ?
C8 C9 H9B 108.8(9) . . ?
N7 C9 H9A 107.9(10) . . ?
C8 C9 H9A 112.6(10) . . ?
H9B C9 H9A 107.5(14) . . ?
N9 N10 N11 106.32(13) . . ?
N10 N11 C10 105.61(13) . . ?
N8 C10 N12 124.27(16) . . ?
N8 C10 N11 112.54(14) . . ?
N12 C10 N11 123.19(16) . . ?
C10 N12 H121 116.9(13) . . ?
C10 N12 H122 118.1(14) . . ?
H121 N12 H122 124.9(19) . . ?
C5 N6 H61 114.0(14) . . ?
C5 N6 H62 113.0(10) . . ?
H61 N6 H62 118.1(18) . . ?
O4 C6 C8 91.07(13) . . ?
O4 C6 H6B 112.8(10) . . ?
C8 C6 H6B 114.4(10) . . ?
O4 C6 H6A 110.7(11) . . ?
C8 C6 H6A 113.1(10) . . ?
H6B C6 H6A 112.8(15) . . ?
N4 N5 C5 106.05(13) . . ?
N2 C5 N5 112.55(13) . . ?
N2 C5 N6 125.01(15) . . ?
N5 C5 N6 122.32(14) . . ?

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 O1 C1 C3 6.49(12) . . . . ?
C1 O1 C2 C3 -6.50(12) . . . . ?
C5 N2 N3 N4 -0.82(18) . . . . ?
C5 N2 N3 C3 -179.89(15) . . . . ?
N4 N3 C3 C4 9.6(2) . . . . ?
N2 N3 C3 C4 -171.40(14) . . . . ?
N4 N3 C3 C2 -126.08(16) . . . . ?
N2 N3 C3 C2 52.9(2) . . . . ?
N4 N3 C3 C1 139.25(16) . . . . ?
N2 N3 C3 C1 -41.7(2) . . . . ?
O1 C2 C3 N3 -106.79(14) . . . . ?
O1 C2 C3 C4 122.16(15) . . . . ?
O1 C2 C3 C1 6.13(12) . . . . ?
O1 C1 C3 N3 107.12(14) . . . . ?
O1 C1 C3 C4 -126.13(14) . . . . ?
O1 C1 C3 C2 -6.17(12) . . . . ?
N2 N3 N4 N5 0.63(19) . . . . ?
C3 N3 N4 N5 179.71(14) . . . . ?
O2 N1 C4 C3 151.36(14) . . . . ?
O3 N1 C4 C3 -31.1(2) . . . . ?
N3 C3 C4 N1 -65.65(18) . . . . ?
C2 C3 C4 N1 67.1(2) . . . . ?
C1 C3 C4 N1 165.84(14) . . . . ?
C6 O4 C7 C8 -1.70(13) . . . . ?
C10 N8 N9 N10 -0.56(19) . . . . ?
C10 N8 N9 C8 -177.64(15) . . . . ?
N10 N9 C8 C9 18.7(2) . . . . ?
N8 N9 C8 C9 -164.47(15) . . . . ?
N10 N9 C8 C7 -118.87(17) . . . . ?
N8 N9 C8 C7 57.9(2) . . . . ?
N10 N9 C8 C6 145.64(16) . . . . ?
N8 N9 C8 C6 -37.6(2) . . . . ?
O4 C7 C8 N9 -111.04(14) . . . . ?
O4 C7 C8 C9 113.75(15) . . . . ?
O4 C7 C8 C6 1.60(12) . . . . ?
O6 N7 C9 C8 -46.3(2) . . . . ?
O5 N7 C9 C8 136.21(15) . . . . ?
N9 C8 C9 N7 -60.53(19) . . . . ?
C7 C8 C9 N7 75.19(19) . . . . ?
C6 C8 C9 N7 172.10(14) . . . . ?
N8 N9 N10 N11 0.59(19) . . . . ?
C8 N9 N10 N11 177.57(14) . . . . ?
N9 N10 N11 C10 -0.34(18) . . . . ?
N9 N8 C10 N12 -179.99(17) . . . . ?
N9 N8 C10 N11 0.32(19) . . . . ?
N10 N11 C10 N8 0.0(2) . . . . ?
N10 N11 C10 N12 -179.69(17) . . . . ?
C7 O4 C6 C8 1.70(13) . . . . ?
N9 C8 C6 O4 112.45(14) . . . . ?
C9 C8 C6 O4 -120.06(14) . . . . ?
C7 C8 C6 O4 -1.61(12) . . . . ?
N3 N4 N5 C5 -0.14(17) . . . . ?
N3 N2 C5 N5 0.70(18) . . . . ?
N3 N2 C5 N6 -175.26(16) . . . . ?
N4 N5 C5 N2 -0.38(19) . . . . ?
N4 N5 C5 N6 175.70(16) . . . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.049

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ca_5at_sp
_database_code_depnum_ccdc_archive 'CCDC 2119621'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-11-01 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
N,2-bis(3-(nitromethyl)oxetan-3-yl)-2H-tetrazol-5-amine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H13 N7 O6'
_chemical_formula_sum            'C9 H13 N7 O6'
_chemical_formula_weight         315.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3155(17)
_cell_length_b                   10.2060(10)
_cell_length_c                   11.8112(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.753(14)
_cell_angle_gamma                90
_cell_volume                     1319.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1015
_cell_measurement_theta_min      2.6450
_cell_measurement_theta_max      27.0900

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87805
_exptl_absorpt_correction_T_max  1.00000
_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.
;
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            8479
_diffrn_reflns_av_unetI/netI     0.1008
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2682
_reflns_number_gt                1653
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0142P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2682
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.17074(17) -0.07895(14) 0.83881(13) 0.0261(5) Uani 1 1 d . . . . .
C1 C 0.2709(3) -0.1266(2) 0.7934(2) 0.0211(7) Uani 1 1 d . . . . .
N1 N 0.0522(2) -0.27528(19) 0.51876(18) 0.0244(6) Uani 1 1 d . . . . .
N2 N 0.27834(19) 0.06871(16) 0.60940(16) 0.0172(5) Uani 1 1 d . . . . .
C2 C 0.0940(3) -0.0614(3) 0.7207(2) 0.0216(7) Uani 1 1 d . . . . .
O2 O -0.02270(17) -0.18701(16) 0.49952(15) 0.0338(5) Uani 1 1 d . . . . .
O3 O 0.0465(2) -0.37234(18) 0.45803(17) 0.0541(7) Uani 1 1 d . . . . .
N3 N 0.23242(18) -0.05260(17) 0.58429(16) 0.0158(5) Uani 1 1 d . . . . .
C3 C 0.1880(2) -0.1308(2) 0.66843(19) 0.0154(6) Uani 1 1 d . . . . .
O5 O 0.0737(2) 0.34581(19) 0.2661(2) 0.0623(8) Uani 1 1 d . . . . .
N5 N 0.2747(2) 0.00562(17) 0.42677(16) 0.0213(5) Uani 1 1 d . . . . .
C5 C 0.3019(2) 0.1013(2) 0.5082(2) 0.0170(6) Uani 1 1 d . . . . .
O6 O 0.2290(2) 0.4607(2) 0.35848(17) 0.0499(7) Uani 1 1 d . . . . .
C6 C 0.3803(2) 0.2464(2) 0.3804(2) 0.0200(6) Uani 1 1 d . . . . .
N6 N 0.3522(2) 0.21731(19) 0.48996(17) 0.0222(6) Uani 1 1 d . . . . .
H9 H 0.359(2) 0.285(2) 0.540(2) 0.034(8) Uiso 1 1 d . . . . .
C9 C 0.4787(3) 0.3515(3) 0.3894(3) 0.0302(8) Uani 1 1 d . . . . .
C8 C 0.4741(3) 0.1560(2) 0.3459(3) 0.0244(7) Uani 1 1 d . . . . .
N7 N 0.1836(3) 0.3629(2) 0.3037(2) 0.0394(7) Uani 1 1 d . . . . .
C7 C 0.2682(3) 0.2615(3) 0.2798(2) 0.0290(7) Uani 1 1 d . . . . .
H1 H 0.133(2) -0.3171(18) 0.6809(17) 0.011(6) Uiso 1 1 d . . . . .
H13 H 0.225(2) -0.3084(19) 0.6045(17) 0.012(6) Uiso 1 1 d . . . . .
H2 H 0.3019(19) -0.2115(19) 0.8310(16) 0.014 Uiso 1 1 d . U . . .
H15 H 0.335(2) -0.062(2) 0.8044(17) 0.021(7) Uiso 1 1 d . . . . .
H3 H 0.085(2) 0.026(2) 0.6974(18) 0.026 Uiso 1 1 d . U . . .
H19 H 0.018(2) -0.109(2) 0.7126(19) 0.025(7) Uiso 1 1 d . . . . .
H4 H 0.214(2) 0.180(2) 0.2544(17) 0.019(6) Uiso 1 1 d . . . . .
O4 O 0.55245(17) 0.26692(15) 0.33673(15) 0.0308(5) Uani 1 1 d . . . . .
N4 N 0.2295(2) -0.09257(17) 0.47786(16) 0.0221(5) Uani 1 1 d . . . . .
C4 C 0.1582(3) -0.2681(2) 0.6238(2) 0.0180(6) Uani 1 1 d . . . . .
H20 H 0.289(2) 0.291(2) 0.206(2) 0.031(7) Uiso 1 1 d . . . . .
H5 H 0.517(2) 0.0969(19) 0.4132(18) 0.023(7) Uiso 1 1 d . . . . .
H21 H 0.448(2) 0.1128(18) 0.2717(18) 0.017(7) Uiso 1 1 d . . . . .
H6 H 0.523(2) 0.3655(19) 0.469(2) 0.026(7) Uiso 1 1 d . . . . .
H22 H 0.454(2) 0.428(2) 0.3430(19) 0.032(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C2 1.454(3) . ?
O1 C1 1.455(3) . ?
C1 C3 1.535(3) . ?
C1 H2 0.996(19) . ?
C1 H15 0.97(2) . ?
N1 O3 1.215(2) . ?
N1 O2 1.218(2) . ?
N1 C4 1.492(3) . ?
N2 C5 1.331(3) . ?
N2 N3 1.346(2) . ?
C2 C3 1.533(3) . ?
C2 H3 0.93(2) . ?
C2 H19 0.97(2) . ?
N3 N4 1.314(2) . ?
N3 C3 1.460(3) . ?
C3 C4 1.504(3) . ?
O5 N7 1.222(3) . ?
N5 N4 1.337(2) . ?
N5 C5 1.350(3) . ?
C5 N6 1.355(3) . ?
O6 N7 1.228(3) . ?
C6 N6 1.440(3) . ?
C6 C7 1.508(4) . ?
C6 C9 1.531(4) . ?
C6 C8 1.538(4) . ?
N6 H9 0.90(2) . ?
C9 O4 1.447(3) . ?
C9 H6 0.96(2) . ?
C9 H22 0.95(2) . ?
C8 O4 1.459(3) . ?
C8 H5 1.02(2) . ?
C8 H21 0.96(2) . ?
N7 C7 1.485(4) . ?
C7 H4 1.03(2) . ?
C7 H20 1.00(2) . ?
C4 H1 0.94(2) . ?
C4 H13 0.94(2) . ?

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 O1 C1 91.06(18) . . ?
O1 C1 C3 91.2(2) . . ?
O1 C1 H2 110.2(12) . . ?
C3 C1 H2 117.7(11) . . ?
O1 C1 H15 110.7(14) . . ?
C3 C1 H15 113.8(12) . . ?
H2 C1 H15 111.4(18) . . ?
O3 N1 O2 124.3(2) . . ?
O3 N1 C4 116.2(2) . . ?
O2 N1 C4 119.5(2) . . ?
C5 N2 N3 100.74(18) . . ?
O1 C2 C3 91.35(19) . . ?
O1 C2 H3 113.4(13) . . ?
C3 C2 H3 111.2(15) . . ?
O1 C2 H19 109.4(13) . . ?
C3 C2 H19 114.7(14) . . ?
H3 C2 H19 115(2) . . ?
N4 N3 N2 114.24(19) . . ?
N4 N3 C3 123.52(18) . . ?
N2 N3 C3 122.23(18) . . ?
N3 C3 C4 110.8(2) . . ?
N3 C3 C2 114.60(19) . . ?
C4 C3 C2 117.1(2) . . ?
N3 C3 C1 114.0(2) . . ?
C4 C3 C1 112.98(19) . . ?
C2 C3 C1 85.19(19) . . ?
N4 N5 C5 105.35(18) . . ?
N2 C5 N5 113.4(2) . . ?
N2 C5 N6 123.3(2) . . ?
N5 C5 N6 123.2(2) . . ?
N6 C6 C7 113.3(2) . . ?
N6 C6 C9 113.9(2) . . ?
C7 C6 C9 115.7(2) . . ?
N6 C6 C8 116.1(2) . . ?
C7 C6 C8 110.6(2) . . ?
C9 C6 C8 84.2(2) . . ?
C5 N6 C6 121.4(2) . . ?
C5 N6 H9 122.4(16) . . ?
C6 N6 H9 115.5(15) . . ?
O4 C9 C6 92.33(19) . . ?
O4 C9 H6 107.6(15) . . ?
C6 C9 H6 111.0(14) . . ?
O4 C9 H22 110.8(15) . . ?
C6 C9 H22 115.8(16) . . ?
H6 C9 H22 116.5(18) . . ?
O4 C8 C6 91.61(18) . . ?
O4 C8 H5 109.9(13) . . ?
C6 C8 H5 111.9(13) . . ?
O4 C8 H21 109.8(13) . . ?
C6 C8 H21 116.6(14) . . ?
H5 C8 H21 114.6(17) . . ?
O5 N7 O6 123.9(3) . . ?
O5 N7 C7 118.5(3) . . ?
O6 N7 C7 117.6(3) . . ?
N7 C7 C6 112.0(2) . . ?
N7 C7 H4 105.0(13) . . ?
C6 C7 H4 117.5(11) . . ?
N7 C7 H20 105.3(13) . . ?
C6 C7 H20 112.0(15) . . ?
H4 C7 H20 104.0(17) . . ?
C9 O4 C8 90.2(2) . . ?
N3 N4 N5 106.25(17) . . ?
N1 C4 C3 113.4(2) . . ?
N1 C4 H1 104.3(13) . . ?
C3 C4 H1 109.0(12) . . ?
N1 C4 H13 107.6(13) . . ?
C3 C4 H13 111.9(13) . . ?
H1 C4 H13 110.3(18) . . ?

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 O1 C1 C3 -8.40(18) . . . . ?
C1 O1 C2 C3 8.41(19) . . . . ?
C5 N2 N3 N4 1.0(3) . . . . ?
C5 N2 N3 C3 -178.0(2) . . . . ?
N4 N3 C3 C4 9.0(3) . . . . ?
N2 N3 C3 C4 -172.2(2) . . . . ?
N4 N3 C3 C2 -126.2(2) . . . . ?
N2 N3 C3 C2 52.6(3) . . . . ?
N4 N3 C3 C1 137.8(2) . . . . ?
N2 N3 C3 C1 -43.3(3) . . . . ?
O1 C2 C3 N3 -122.26(19) . . . . ?
O1 C2 C3 C4 105.4(2) . . . . ?
O1 C2 C3 C1 -8.00(18) . . . . ?
O1 C1 C3 N3 122.8(2) . . . . ?
O1 C1 C3 C4 -109.4(2) . . . . ?
O1 C1 C3 C2 7.99(18) . . . . ?
N3 N2 C5 N5 -1.2(3) . . . . ?
N3 N2 C5 N6 -179.0(2) . . . . ?
N4 N5 C5 N2 1.0(3) . . . . ?
N4 N5 C5 N6 178.8(2) . . . . ?
N2 C5 N6 C6 177.7(2) . . . . ?
N5 C5 N6 C6 0.1(4) . . . . ?
C7 C6 N6 C5 67.9(3) . . . . ?
C9 C6 N6 C5 -157.1(2) . . . . ?
C8 C6 N6 C5 -61.7(3) . . . . ?
N6 C6 C9 O4 125.5(2) . . . . ?
C7 C6 C9 O4 -100.7(2) . . . . ?
C8 C6 C9 O4 9.5(2) . . . . ?
N6 C6 C8 O4 -123.2(2) . . . . ?
C7 C6 C8 O4 106.0(2) . . . . ?
C9 C6 C8 O4 -9.4(2) . . . . ?
O5 N7 C7 C6 -144.9(3) . . . . ?
O6 N7 C7 C6 36.5(3) . . . . ?
N6 C6 C7 N7 56.0(3) . . . . ?
C9 C6 C7 N7 -78.1(3) . . . . ?
C8 C6 C7 N7 -171.7(2) . . . . ?
C6 C9 O4 C8 -9.9(2) . . . . ?
C6 C8 O4 C9 9.9(2) . . . . ?
N2 N3 N4 N5 -0.4(3) . . . . ?
C3 N3 N4 N5 178.5(2) . . . . ?
C5 N5 N4 N3 -0.4(3) . . . . ?
O3 N1 C4 C3 158.1(2) . . . . ?
O2 N1 C4 C3 -22.7(4) . . . . ?
N3 C3 C4 N1 -66.8(3) . . . . ?
C2 C3 C4 N1 67.2(3) . . . . ?
C1 C3 C4 N1 163.8(2) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.054

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lsg002_1
_database_code_depnum_ccdc_archive 'CCDC 2119620'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-11-01 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
1-(3-(nitromethyl)oxetan-3-yl)-1H-tetrazol-5-amine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H8 N6 O3'
_chemical_formula_sum            'C5 H8 N6 O3'
_chemical_formula_weight         200.17

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9708(2)
_cell_length_b                   5.9762(4)
_cell_length_c                   23.6021(13)
_cell_angle_alpha                96.514(5)
_cell_angle_beta                 94.962(4)
_cell_angle_gamma                94.389(4)
_cell_volume                     830.44(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3224
_cell_measurement_theta_min      3.4090
_cell_measurement_theta_max      31.7040

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95235
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            12124
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.618
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3350
_reflns_number_gt                2856
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+1.3726P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3350
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.2455(4) 0.4445(4) 0.22345(10) 0.0196(5) Uani 1 1 d . . . . .
H121 H 0.760(6) 0.346(6) 0.4560(15) 0.031(9) Uiso 1 1 d . . . . .
C1 C 0.1583(5) 0.8425(5) 0.15809(12) 0.0201(6) Uani 1 1 d . . . . .
H1A H -0.002(4) 0.8498(5) 0.1499(2) 0.024 Uiso 1 1 calc R U . . .
H1B H 0.2030(11) 0.8818(10) 0.1985(10) 0.024 Uiso 1 1 calc R U . . .
O1 O 0.2910(4) 0.9666(3) 0.12256(9) 0.0308(5) Uani 1 1 d . . . . .
O2 O 0.0881(4) 0.2982(3) 0.21284(9) 0.0271(5) Uani 1 1 d . . . . .
H122 H 0.621(6) 0.216(6) 0.4931(16) 0.033(10) Uiso 1 1 d . . . . .
C2 C 0.3805(5) 0.7662(4) 0.09734(11) 0.0183(6) Uani 1 1 d . . . . .
H2A H 0.543(4) 0.7656(4) 0.1061(2) 0.022 Uiso 1 1 calc R U . . .
H2B H 0.3385(10) 0.7324(9) 0.0562(10) 0.022 Uiso 1 1 calc R U . . .
N2 N 0.0622(4) 0.4667(4) 0.09975(9) 0.0150(5) Uani 1 1 d . . . . .
O3 O 0.2962(5) 0.5507(4) 0.27100(9) 0.0386(6) Uani 1 1 d . . . . .
H61 H 0.377(6) 0.289(5) 0.0445(14) 0.022(8) Uiso 1 1 d . . . . .
C3 C 0.2415(4) 0.6182(4) 0.13335(11) 0.0154(5) Uani 1 1 d . . . . .
N3 N -0.1553(4) 0.4660(4) 0.11411(10) 0.0206(5) Uani 1 1 d . . . . .
O4 O 1.3520(3) 0.1727(4) 0.38200(9) 0.0289(5) Uani 1 1 d . . . . .
H62 H 0.222(6) 0.138(7) 0.0071(16) 0.034(10) Uiso 1 1 d . . . . .
C4 C 0.3814(4) 0.4968(5) 0.17564(11) 0.0163(5) Uani 1 1 d . . . . .
H4A H 0.4268(11) 0.355(3) 0.1558(4) 0.020 Uiso 1 1 calc R U . . .
H4B H 0.520(3) 0.594(2) 0.1911(3) 0.020 Uiso 1 1 calc R U . . .
N4 N -0.2706(4) 0.3110(4) 0.07910(10) 0.0229(5) Uani 1 1 d . . . . .
N5 N -0.1395(4) 0.2045(4) 0.04152(10) 0.0194(5) Uani 1 1 d . . . . .
C5 C 0.0666(4) 0.3049(4) 0.05483(11) 0.0154(5) Uani 1 1 d . . . . .
N6 N 0.2479(4) 0.2633(4) 0.02623(10) 0.0172(5) Uani 1 1 d . . . . .
C6 C 1.1720(4) 0.2999(5) 0.40175(11) 0.0182(6) Uani 1 1 d . . . . .
H6A H 1.1758(4) 0.454(4) 0.3899(3) 0.022 Uiso 1 1 calc R U . . .
H6B H 1.1612(5) 0.3053(5) 0.4435(10) 0.022 Uiso 1 1 calc R U . . .
O6 O 0.8134(4) -0.1201(4) 0.26625(9) 0.0279(5) Uani 1 1 d . . . . .
C7 C 1.1985(4) 0.0308(5) 0.34011(12) 0.0189(6) Uani 1 1 d . . . . .
H7A H 1.2044(5) -0.130(4) 0.34308(13) 0.023 Uiso 1 1 calc R U . . .
H7B H 1.2142(6) 0.0620(8) 0.3010(9) 0.023 Uiso 1 1 calc R U . . .
N7 N 0.7302(4) 0.0599(4) 0.27458(10) 0.0199(5) Uani 1 1 d . . . . .
O5 O 0.5745(4) 0.1169(4) 0.24424(9) 0.0344(6) Uani 1 1 d . . . . .
N8 N 0.8772(4) -0.0249(4) 0.39976(9) 0.0149(5) Uani 1 1 d . . . . .
C8 C 0.9921(4) 0.1298(4) 0.36534(10) 0.0138(5) Uani 1 1 d . . . . .
N9 N 0.8668(4) -0.2537(4) 0.38585(10) 0.0208(5) Uani 1 1 d . . . . .
C9 C 0.8262(4) 0.2290(4) 0.32500(11) 0.0167(5) Uani 1 1 d . . . . .
H9A H 0.704(3) 0.2816(13) 0.3459(5) 0.020 Uiso 1 1 calc R U . . .
H9B H 0.9015(17) 0.358(3) 0.3110(3) 0.020 Uiso 1 1 calc R U . . .
N11 N 0.6761(4) -0.1775(4) 0.45999(10) 0.0190(5) Uani 1 1 d . . . . .
N10 N 0.7482(4) -0.3396(4) 0.42203(10) 0.0237(5) Uani 1 1 d . . . . .
C10 C 0.7596(4) 0.0180(4) 0.44560(11) 0.0145(5) Uani 1 1 d . . . . .
N12 N 0.7402(4) 0.2233(4) 0.47446(10) 0.0164(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 O2 1.222(3) . ?
N1 O3 1.226(3) . ?
N1 C4 1.493(3) . ?
C1 O1 1.431(3) . ?
C1 C3 1.536(4) . ?
C1 H1A 0.96(2) . ?
C1 H1B 0.96(2) . ?
O1 C2 1.437(3) . ?
C2 C3 1.541(4) . ?
C2 H2A 0.98(2) . ?
C2 H2B 0.98(2) . ?
N2 C5 1.355(3) . ?
N2 N3 1.370(3) . ?
N2 C3 1.462(3) . ?
C3 C4 1.528(4) . ?
N3 N4 1.283(3) . ?
O4 C7 1.439(3) . ?
O4 C6 1.443(3) . ?
C4 H4A 0.99(2) . ?
C4 H4B 0.99(2) . ?
N4 N5 1.368(3) . ?
N5 C5 1.323(3) . ?
C5 N6 1.349(3) . ?
N6 H61 0.84(4) . ?
N6 H62 0.83(4) . ?
C6 C8 1.550(4) . ?
C6 H6A 0.99(2) . ?
C6 H6B 0.99(2) . ?
O6 N7 1.222(3) . ?
C7 C8 1.544(4) . ?
C7 H7A 0.97(2) . ?
C7 H7B 0.97(2) . ?
N7 O5 1.217(3) . ?
N7 C9 1.512(3) . ?
N8 C10 1.351(3) . ?
N8 N9 1.364(3) . ?
N8 C8 1.468(3) . ?
C8 C9 1.515(4) . ?
N9 N10 1.282(3) . ?
C9 H9A 0.97(2) . ?
C9 H9B 0.97(2) . ?
N11 C10 1.326(3) . ?
N11 N10 1.364(3) . ?
C10 N12 1.352(3) . ?
N12 H121 0.90(4) . ?
N12 H122 0.87(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
O2 N1 O3 123.5(2) . . ?
O2 N1 C4 117.9(2) . . ?
O3 N1 C4 118.6(2) . . ?
O1 C1 C3 91.6(2) . . ?
O1 C1 H1A 113.4 . . ?
C3 C1 H1A 113.4 . . ?
O1 C1 H1B 113.4 . . ?
C3 C1 H1B 113.4 . . ?
H1A C1 H1B 110.7 . . ?
C1 O1 C2 92.59(19) . . ?
O1 C2 C3 91.12(19) . . ?
O1 C2 H2A 113.4 . . ?
C3 C2 H2A 113.4 . . ?
O1 C2 H2B 113.4 . . ?
C3 C2 H2B 113.4 . . ?
H2A C2 H2B 110.7 . . ?
C5 N2 N3 107.8(2) . . ?
C5 N2 C3 131.7(2) . . ?
N3 N2 C3 120.3(2) . . ?
N2 C3 C4 112.2(2) . . ?
N2 C3 C1 112.8(2) . . ?
C4 C3 C1 115.8(2) . . ?
N2 C3 C2 114.0(2) . . ?
C4 C3 C2 114.8(2) . . ?
C1 C3 C2 84.73(19) . . ?
N4 N3 N2 106.1(2) . . ?
C7 O4 C6 91.71(19) . . ?
N1 C4 C3 109.6(2) . . ?
N1 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N3 N4 N5 112.0(2) . . ?
C5 N5 N4 105.5(2) . . ?
N5 C5 N6 125.7(2) . . ?
N5 C5 N2 108.6(2) . . ?
N6 C5 N2 125.5(2) . . ?
C5 N6 H61 118(2) . . ?
C5 N6 H62 108(3) . . ?
H61 N6 H62 115(3) . . ?
O4 C6 C8 91.31(19) . . ?
O4 C6 H6A 113.4 . . ?
C8 C6 H6A 113.4 . . ?
O4 C6 H6B 113.4 . . ?
C8 C6 H6B 113.4 . . ?
H6A C6 H6B 110.7 . . ?
O4 C7 C8 91.7(2) . . ?
O4 C7 H7A 113.3 . . ?
C8 C7 H7A 113.3 . . ?
O4 C7 H7B 113.3 . . ?
C8 C7 H7B 113.3 . . ?
H7A C7 H7B 110.7 . . ?
O5 N7 O6 124.4(2) . . ?
O5 N7 C9 116.4(2) . . ?
O6 N7 C9 119.2(2) . . ?
C10 N8 N9 108.0(2) . . ?
C10 N8 C8 130.6(2) . . ?
N9 N8 C8 121.3(2) . . ?
N8 C8 C9 111.7(2) . . ?
N8 C8 C7 112.2(2) . . ?
C9 C8 C7 117.5(2) . . ?
N8 C8 C6 112.7(2) . . ?
C9 C8 C6 116.2(2) . . ?
C7 C8 C6 83.90(19) . . ?
N10 N9 N8 106.2(2) . . ?
N7 C9 C8 112.4(2) . . ?
N7 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
N7 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C10 N11 N10 105.5(2) . . ?
N9 N10 N11 111.9(2) . . ?
N11 C10 N8 108.4(2) . . ?
N11 C10 N12 125.1(2) . . ?
N8 C10 N12 126.4(2) . . ?
C10 N12 H121 118(2) . . ?
C10 N12 H122 109(2) . . ?
H121 N12 H122 116(3) . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.067

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ca5azt
_database_code_depnum_ccdc_archive 'CCDC 2119622'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-11-01 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
5-azido-2-(3-(nitromethyl)oxetan-3-yl)-2H-tetrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H6 N8 O3'
_chemical_formula_sum            'C5 H6 N8 O3'
_chemical_formula_weight         226.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0695(5)
_cell_length_b                   7.1343(2)
_cell_length_c                   12.2573(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.469(5)
_cell_angle_gamma                90
_cell_volume                     912.65(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4152
_cell_measurement_theta_min      2.8960
_cell_measurement_theta_max      31.9950

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91555
_exptl_absorpt_correction_T_max  1.00000
_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.
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            17638
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.035
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2778
_reflns_number_gt                2308
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+0.2007P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2778
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.34047(8) 0.54002(10) 0.44756(6) 0.02161(17) Uani 1 1 d . . . . .
H1B H 0.2390(13) 0.3055(18) 0.3901(11) 0.021(3) Uiso 1 1 d . . . . .
H1A H 0.3869(12) 0.2764(17) 0.4184(10) 0.017(3) Uiso 1 1 d . . . . .
N1 N 0.46487(8) 0.03438(12) 0.63917(8) 0.01856(17) Uani 1 1 d . . . . .
C1 C 0.32180(10) 0.33853(14) 0.44114(9) 0.01860(19) Uani 1 1 d . . . . .
O2 O 0.54028(8) -0.05151(11) 0.71921(7) 0.02880(19) Uani 1 1 d . . . . .
H2B H 0.2730(12) 0.6049(17) 0.5757(11) 0.018(3) Uiso 1 1 d . . . . .
H2A H 0.4241(12) 0.5999(17) 0.6180(11) 0.018(3) Uiso 1 1 d . . . . .
N2 N 0.10659(8) 0.29039(13) 0.52982(8) 0.02050(18) Uani 1 1 d . . . . .
C2 C 0.34478(10) 0.54399(13) 0.56724(9) 0.01800(19) Uani 1 1 d . . . . .
O3 O 0.39668(8) -0.03748(10) 0.54872(7) 0.02442(17) Uani 1 1 d . . . . .
N3 N 0.22702(8) 0.25304(12) 0.59578(7) 0.01673(17) Uani 1 1 d . . . . .
C3 C 0.33813(9) 0.32815(13) 0.57098(8) 0.01570(18) Uani 1 1 d . . . . .
C4 C 0.45969(9) 0.24279(13) 0.65201(9) 0.01723(19) Uani 1 1 d . . . . .
H4A H 0.5305(13) 0.2898(19) 0.6314(11) 0.024(3) Uiso 1 1 d . . . . .
H4B H 0.4713(11) 0.2654(17) 0.7341(10) 0.017(3) Uiso 1 1 d . . . . .
N4 N 0.23731(8) 0.14643(13) 0.68647(8) 0.02124(19) Uani 1 1 d . . . . .
N5 N 0.11926(8) 0.10827(13) 0.68224(8) 0.02144(19) Uani 1 1 d . . . . .
C5 C 0.04302(9) 0.19836(14) 0.58757(9) 0.01853(19) Uani 1 1 d . . . . .
N8 N -0.18986(9) 0.07579(14) 0.67784(8) 0.0269(2) Uani 1 1 d . . . . .
N7 N -0.13595(8) 0.13034(12) 0.62187(8) 0.02023(18) Uani 1 1 d . . . . .
N6 N -0.09063(8) 0.19540(14) 0.54869(8) 0.0242(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.4507(12) . ?
O1 C2 1.4521(12) . ?
N1 O2 1.2201(11) . ?
N1 O3 1.2263(11) . ?
N1 C4 1.4983(12) . ?
C1 C3 1.5424(14) . ?
C1 H1B 0.951(13) . ?
C1 H1A 0.963(13) . ?
N2 C5 1.3264(13) . ?
N2 N3 1.3354(11) . ?
C2 C3 1.5431(13) . ?
C2 H2B 0.941(13) . ?
C2 H2A 0.976(13) . ?
N3 N4 1.3202(11) . ?
N3 C3 1.4634(12) . ?
C3 C4 1.5090(13) . ?
C4 H4A 0.960(14) . ?
C4 H4B 0.984(12) . ?
N4 N5 1.3188(12) . ?
N5 C5 1.3487(13) . ?
C5 N6 1.3952(13) . ?
N8 N7 1.1186(13) . ?
N7 N6 1.2536(12) . ?

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
C1 O1 C2 91.73(7) . . ?
O2 N1 O3 124.54(9) . . ?
O2 N1 C4 116.99(8) . . ?
O3 N1 C4 118.44(8) . . ?
O1 C1 C3 91.49(7) . . ?
O1 C1 H1B 111.7(8) . . ?
C3 C1 H1B 115.0(8) . . ?
O1 C1 H1A 111.4(7) . . ?
C3 C1 H1A 115.8(7) . . ?
H1B C1 H1A 110.2(11) . . ?
C5 N2 N3 100.27(8) . . ?
O1 C2 C3 91.41(7) . . ?
O1 C2 H2B 112.0(8) . . ?
C3 C2 H2B 114.0(8) . . ?
O1 C2 H2A 111.8(7) . . ?
C3 C2 H2A 115.5(7) . . ?
H2B C2 H2A 110.8(11) . . ?
N4 N3 N2 114.41(8) . . ?
N4 N3 C3 122.90(8) . . ?
N2 N3 C3 122.67(8) . . ?
N3 C3 C4 110.02(8) . . ?
N3 C3 C1 114.47(8) . . ?
C4 C3 C1 118.08(8) . . ?
N3 C3 C2 115.04(8) . . ?
C4 C3 C2 112.42(8) . . ?
C1 C3 C2 84.94(7) . . ?
N1 C4 C3 112.85(8) . . ?
N1 C4 H4A 104.8(8) . . ?
C3 C4 H4A 108.2(8) . . ?
N1 C4 H4B 105.9(7) . . ?
C3 C4 H4B 113.0(7) . . ?
H4A C4 H4B 111.8(10) . . ?
N5 N4 N3 106.23(8) . . ?
N4 N5 C5 105.26(8) . . ?
N2 C5 N5 113.82(9) . . ?
N2 C5 N6 121.07(9) . . ?
N5 C5 N6 125.09(9) . . ?
N8 N7 N6 171.96(11) . . ?
N7 N6 C5 113.13(9) . . ?

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 O1 C1 C3 -5.05(8) . . . . ?
C1 O1 C2 C3 5.05(8) . . . . ?
C5 N2 N3 N4 0.20(11) . . . . ?
C5 N2 N3 C3 -178.32(9) . . . . ?
N4 N3 C3 C4 8.36(13) . . . . ?
N2 N3 C3 C4 -173.24(8) . . . . ?
N4 N3 C3 C1 144.10(9) . . . . ?
N2 N3 C3 C1 -37.50(12) . . . . ?
N4 N3 C3 C2 -119.83(10) . . . . ?
N2 N3 C3 C2 58.57(12) . . . . ?
O1 C1 C3 N3 120.02(8) . . . . ?
O1 C1 C3 C4 -107.98(9) . . . . ?
O1 C1 C3 C2 4.77(7) . . . . ?
O1 C2 C3 N3 -119.45(8) . . . . ?
O1 C2 C3 C4 113.57(8) . . . . ?
O1 C2 C3 C1 -4.77(7) . . . . ?
O2 N1 C4 C3 -161.05(9) . . . . ?
O3 N1 C4 C3 21.02(12) . . . . ?
N3 C3 C4 N1 61.71(10) . . . . ?
C1 C3 C4 N1 -72.24(11) . . . . ?
C2 C3 C4 N1 -168.67(8) . . . . ?
N2 N3 N4 N5 0.35(12) . . . . ?
C3 N3 N4 N5 178.87(9) . . . . ?
N3 N4 N5 C5 -0.73(11) . . . . ?
N3 N2 C5 N5 -0.69(11) . . . . ?
N3 N2 C5 N6 -179.17(9) . . . . ?
N4 N5 C5 N2 0.94(12) . . . . ?
N4 N5 C5 N6 179.34(10) . . . . ?
N2 C5 N6 N7 -168.67(10) . . . . ?
N5 C5 N6 N7 13.04(15) . . . . ?

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.045

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_max
_database_code_depnum_ccdc_archive 'CCDC 2119623'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-11-01 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
2-(3-(nitromethyl)oxetan-3-yl)-2H-tetrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H7 N5 O3'
_chemical_formula_sum            'C5 H7 N5 O3'
_chemical_formula_weight         185.16

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   10.3115(6)
_cell_length_b                   10.3339(7)
_cell_length_c                   7.3393(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.240(7)
_cell_angle_gamma                90
_cell_volume                     764.28(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    102(2)
_cell_measurement_reflns_used    1577
_cell_measurement_theta_min      2.7970
_cell_measurement_theta_max      28.9170

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91105
_exptl_absorpt_correction_T_max  1.00000
_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.
;
_diffrn_ambient_temperature      102(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            4582
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.823
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1552
_reflns_number_gt                1309
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+0.2081P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1552
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.41010(10) 0.37908(10) 0.42422(13) 0.0233(3) Uani 1 1 d . . . . .
H1B H 0.3730(16) 0.2637(16) 0.635(2) 0.022(4) Uiso 1 1 d . . . . .
H1A H 0.4799(15) 0.3801(14) 0.704(2) 0.017(4) Uiso 1 1 d . . . . .
C1 C 0.39866(14) 0.35494(15) 0.6152(2) 0.0192(3) Uani 1 1 d . . . . .
N1 N 0.33216(11) 0.56143(11) 0.90868(17) 0.0193(3) Uani 1 1 d . . . . .
C2 C 0.29385(14) 0.46166(15) 0.3905(2) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.11739(12) 0.27878(12) 0.55703(18) 0.0246(3) Uani 1 1 d . . . . .
H2B H 0.2208(15) 0.4224(14) 0.305(2) 0.017(4) Uiso 1 1 d . . . . .
H2A H 0.3128(13) 0.5503(14) 0.351(2) 0.011(3) Uiso 1 1 d . . . . .
O2 O 0.32437(11) 0.65990(11) 0.99861(15) 0.0324(3) Uani 1 1 d . . . . .
O3 O 0.35915(11) 0.45477(10) 0.97703(14) 0.0254(3) Uani 1 1 d . . . . .
C3 C 0.28321(13) 0.45112(13) 0.59728(19) 0.0163(3) Uani 1 1 d . . . . .
N3 N 0.15826(11) 0.39478(11) 0.62395(16) 0.0173(3) Uani 1 1 d . . . . .
C4 C 0.31120(15) 0.57715(14) 0.70126(19) 0.0186(3) Uani 1 1 d . . . . .
H4A H 0.2414(16) 0.6379(15) 0.666(2) 0.020(4) Uiso 1 1 d . . . . .
H4B H 0.3947(16) 0.6099(15) 0.681(2) 0.019(4) Uiso 1 1 d . . . . .
N4 N 0.07244(12) 0.45674(12) 0.70388(17) 0.0228(3) Uani 1 1 d . . . . .
C5 C -0.00041(15) 0.27209(16) 0.6020(2) 0.0260(4) Uani 1 1 d . . . . .
H5 H -0.0525(18) 0.1994(18) 0.575(3) 0.036(5) Uiso 1 1 d . . . . .
N5 N -0.03028(12) 0.37815(13) 0.69025(18) 0.0271(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C2 1.4493(17) . ?
O1 C1 1.4530(17) . ?
C1 C3 1.5350(19) . ?
C1 H1B 0.998(16) . ?
C1 H1A 0.981(16) . ?
N1 O3 1.2185(15) . ?
N1 O2 1.2247(15) . ?
N1 C4 1.5004(18) . ?
C2 C3 1.5482(19) . ?
C2 H2B 0.963(16) . ?
C2 H2A 0.992(14) . ?
N2 C5 1.3265(19) . ?
N2 N3 1.3297(17) . ?
C3 N3 1.4644(16) . ?
C3 C4 1.5061(19) . ?
N3 N4 1.3256(15) . ?
C4 H4A 0.948(16) . ?
C4 H4B 0.966(16) . ?
N4 N5 1.3216(17) . ?
C5 N5 1.342(2) . ?
C5 H5 0.920(19) . ?

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 O1 C1 91.85(9) . . ?
O1 C1 C3 91.50(10) . . ?
O1 C1 H1B 112.4(9) . . ?
C3 C1 H1B 113.5(9) . . ?
O1 C1 H1A 111.3(8) . . ?
C3 C1 H1A 115.0(9) . . ?
H1B C1 H1A 111.6(13) . . ?
O3 N1 O2 124.40(12) . . ?
O3 N1 C4 119.13(11) . . ?
O2 N1 C4 116.43(11) . . ?
O1 C2 C3 91.11(10) . . ?
O1 C2 H2B 111.6(9) . . ?
C3 C2 H2B 113.8(9) . . ?
O1 C2 H2A 112.7(8) . . ?
C3 C2 H2A 114.1(8) . . ?
H2B C2 H2A 112.0(12) . . ?
C5 N2 N3 100.97(12) . . ?
N3 C3 C4 110.83(11) . . ?
N3 C3 C1 114.80(11) . . ?
C4 C3 C1 117.04(12) . . ?
N3 C3 C2 113.96(11) . . ?
C4 C3 C2 112.95(11) . . ?
C1 C3 C2 85.11(10) . . ?
N4 N3 N2 114.20(11) . . ?
N4 N3 C3 123.78(11) . . ?
N2 N3 C3 121.87(11) . . ?
N1 C4 C3 113.04(11) . . ?
N1 C4 H4A 106.6(9) . . ?
C3 C4 H4A 112.4(9) . . ?
N1 C4 H4B 104.8(9) . . ?
C3 C4 H4B 107.7(9) . . ?
H4A C4 H4B 112.0(13) . . ?
N5 N4 N3 105.61(11) . . ?
N2 C5 N5 113.18(14) . . ?
N2 C5 H5 120.8(11) . . ?
N5 C5 H5 126.0(11) . . ?
N4 N5 C5 106.04(11) . . ?

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 O1 C1 C3 -5.13(11) . . . . ?
C1 O1 C2 C3 5.09(11) . . . . ?
O1 C1 C3 N3 119.00(12) . . . . ?
O1 C1 C3 C4 -108.49(12) . . . . ?
O1 C1 C3 C2 4.82(10) . . . . ?
O1 C2 C3 N3 -119.84(11) . . . . ?
O1 C2 C3 C4 112.51(12) . . . . ?
O1 C2 C3 C1 -4.83(10) . . . . ?
C5 N2 N3 N4 -0.39(15) . . . . ?
C5 N2 N3 C3 -176.00(12) . . . . ?
C4 C3 N3 N4 9.88(18) . . . . ?
C1 C3 N3 N4 145.25(13) . . . . ?
C2 C3 N3 N4 -118.86(14) . . . . ?
C4 C3 N3 N2 -174.94(12) . . . . ?
C1 C3 N3 N2 -39.57(17) . . . . ?
C2 C3 N3 N2 56.33(16) . . . . ?
O3 N1 C4 C3 18.64(17) . . . . ?
O2 N1 C4 C3 -163.44(12) . . . . ?
N3 C3 C4 N1 64.06(15) . . . . ?
C1 C3 C4 N1 -70.22(15) . . . . ?
C2 C3 C4 N1 -166.67(11) . . . . ?
N2 N3 N4 N5 0.24(15) . . . . ?
C3 N3 N4 N5 175.76(12) . . . . ?
N3 N2 C5 N5 0.40(16) . . . . ?
N3 N4 N5 C5 0.02(15) . . . . ?
N2 C5 N5 N4 -0.28(18) . . . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.046

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_test1
_database_code_depnum_ccdc_archive 'CCDC 2119795'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT089_test1               
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.20 Note
RESPONSE: In the crystal the molecule is disordered over two positions. 
;
# Added during the CSD deposition process: Tuesday 02 November 2021 11:09 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
1-(3-(nitromethyl)oxetan-3-yl)-1H-tetrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H7 N5 O3'
_chemical_formula_sum            'C5 H7 N5 O3'
_chemical_formula_weight         185.16

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   13.2428(16)
_cell_length_b                   5.8688(4)
_cell_length_c                   10.8791(10)
_cell_angle_alpha                90
_cell_angle_beta                 116.862(10)
_cell_angle_gamma                90
_cell_volume                     754.28(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1690
_cell_measurement_theta_min      2.1070
_cell_measurement_theta_max      31.9090

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            5947
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.449
_diffrn_reflns_theta_max         30.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2001
_reflns_number_gt                1729
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.993

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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).
;
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+0.2624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2001
_refine_ls_number_parameters     222
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.799
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1A C 0.7693(12) 1.3465(16) 0.5150(9) 0.0250(18) Uani 0.627(6) 1 d D . P A 1
H1A H 0.830252 1.339488 0.486162 0.030 Uiso 0.627(6) 1 calc R U P A 1
H1B H 0.693915 1.346461 0.433776 0.030 Uiso 0.627(6) 1 calc R U P A 1
C2A C 0.7725(9) 1.3705(12) 0.7051(9) 0.0231(15) Uani 0.627(6) 1 d D . P A 1
H2A H 0.698435 1.380715 0.706689 0.028 Uiso 0.627(6) 1 calc R U P A 1
H2B H 0.835347 1.378724 0.799724 0.028 Uiso 0.627(6) 1 calc R U P A 1
C3A C 0.7813(4) 1.1686(9) 0.6230(6) 0.0178(9) Uani 0.627(6) 1 d D . P A 1
C4A C 0.8917(4) 1.0439(9) 0.6912(5) 0.0199(9) Uani 0.627(6) 1 d D . P A 1
H6A H 0.953728 1.156324 0.733865 0.024 Uiso 0.627(6) 1 calc R U P A 1
H6B H 0.891703 0.947387 0.765817 0.024 Uiso 0.627(6) 1 calc R U P A 1
C5A C 0.6098(4) 0.9272(9) 0.4612(5) 0.0260(10) Uani 0.627(6) 1 d D . P A 1
H5A H 0.605(4) 0.971(8) 0.378(4) 0.031 Uiso 0.627(6) 1 d . U P A 1
O1A O 0.7840(5) 1.5281(11) 0.6115(5) 0.0307(11) Uani 0.627(6) 1 d D . P A 1
O2A O 1.0029(4) 0.7860(8) 0.6471(5) 0.0366(11) Uani 0.627(6) 1 d D . P A 1
O3A O 0.85400(18) 0.9070(4) 0.4800(2) 0.0345(5) Uani 0.627(6) 1 d D . P A 1
N1A N 0.9149(3) 0.8969(7) 0.5942(4) 0.0213(9) Uani 0.627(6) 1 d D . P A 1
N2A N 0.6851(3) 1.0123(6) 0.5824(3) 0.0174(8) Uani 0.627(6) 1 d D . P A 1
N5A N 0.66693(19) 0.9105(4) 0.6894(2) 0.0331(5) Uani 0.627(6) 1 d D . P A 1
N4A N 0.5755(4) 0.7879(8) 0.6166(4) 0.0282(10) Uani 0.627(6) 1 d D . P A 1
N3A N 0.5414(4) 0.7939(9) 0.4789(5) 0.0330(11) Uani 0.627(6) 1 d D . P A 1
C1B C 0.7586(18) 1.370(3) 0.4805(13) 0.021(3) Uani 0.373(6) 1 d D . P A 2
H1C H 0.833543 1.386181 0.482139 0.025 Uiso 0.373(6) 1 calc R U P A 2
H1D H 0.697333 1.371258 0.384733 0.025 Uiso 0.373(6) 1 calc R U P A 2
C2B C 0.7673(17) 1.355(3) 0.6722(14) 0.034(4) Uani 0.373(6) 1 d D . P A 2
H2C H 0.711926 1.344278 0.709794 0.041 Uiso 0.373(6) 1 calc R U P A 2
H2D H 0.845601 1.365086 0.747290 0.041 Uiso 0.373(6) 1 calc R U P A 2
C3B C 0.7517(6) 1.1717(15) 0.5643(11) 0.0190(16) Uani 0.373(6) 1 d D . P A 2
C4B C 0.6368(6) 1.0482(16) 0.4904(8) 0.0254(18) Uani 0.373(6) 1 d D . P A 2
H6C H 0.576231 1.163774 0.448783 0.030 Uiso 0.373(6) 1 calc R U P A 2
H6D H 0.636928 0.955132 0.414598 0.030 Uiso 0.373(6) 1 calc R U P A 2
C5B C 0.9160(6) 0.9367(17) 0.7217(8) 0.0287(18) Uani 0.373(6) 1 d D . P A 2
H5B H 0.917918 0.979307 0.806952 0.034 Uiso 0.373(6) 1 calc R U P A 2
O1B O 0.7406(8) 1.525(2) 0.5691(9) 0.0321(19) Uani 0.373(6) 1 d D . P A 2
O2B O 0.5235(5) 0.7896(13) 0.5297(11) 0.042(2) Uani 0.373(6) 1 d D . P A 2
O3B O 0.66693(19) 0.9105(4) 0.6894(2) 0.0331(5) Uani 0.373(6) 1 d D . P A 2
N1B N 0.6097(5) 0.8979(13) 0.5818(7) 0.0275(17) Uani 0.373(6) 1 d D . P A 2
N2B N 0.8452(5) 1.0102(9) 0.6010(6) 0.0211(15) Uani 0.373(6) 1 d D . P A 2
N5B N 0.85400(18) 0.9070(4) 0.4800(2) 0.0345(5) Uani 0.373(6) 1 d D . P A 2
N3B N 0.9908(8) 0.7796(17) 0.7035(9) 0.039(2) Uani 0.373(6) 1 d D . P A 2
N4B N 0.9583(7) 0.7839(14) 0.5701(9) 0.035(2) Uani 0.373(6) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1A O1A 1.446(10) . ?
C1A C3A 1.525(8) . ?
C1A H1A 0.9900 . ?
C1A H1B 0.9900 . ?
C2A O1A 1.435(8) . ?
C2A C3A 1.520(9) . ?
C2A H2A 0.9900 . ?
C2A H2B 0.9900 . ?
C3A N2A 1.467(6) . ?
C3A C4A 1.498(7) . ?
C4A N1A 1.498(6) . ?
C4A H6A 0.9900 . ?
C4A H6B 0.9900 . ?
C5A N3A 1.276(7) . ?
C5A N2A 1.340(5) . ?
C5A H5A 0.91(4) . ?
O2A N1A 1.228(5) . ?
O3A N1A 1.137(4) . ?
N2A N5A 1.423(4) . ?
N5A N4A 1.321(5) . ?
N4A N3A 1.356(6) . ?
C1B O1B 1.422(16) . ?
C1B C3B 1.505(13) . ?
C1B H1C 0.9900 . ?
C1B H1D 0.9900 . ?
C2B O1B 1.422(15) . ?
C2B C3B 1.535(14) . ?
C2B H2C 0.9900 . ?
C2B H2D 0.9900 . ?
C3B N2B 1.465(9) . ?
C3B C4B 1.543(11) . ?
C4B N1B 1.490(9) . ?
C4B H6C 0.9900 . ?
C4B H6D 0.9900 . ?
C5B N2B 1.295(9) . ?
C5B N3B 1.430(12) . ?
C5B H5B 0.9500 . ?
O2B N1B 1.201(9) . ?
O3B N1B 1.072(6) . ?
N2B N5B 1.500(6) . ?
N5B N4B 1.472(10) . ?
N3B N4B 1.315(11) . ?

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
O1A C1A C3A 90.7(5) . . ?
O1A C1A H1A 113.5 . . ?
C3A C1A H1A 113.5 . . ?
O1A C1A H1B 113.5 . . ?
C3A C1A H1B 113.5 . . ?
H1A C1A H1B 110.8 . . ?
O1A C2A C3A 91.3(6) . . ?
O1A C2A H2A 113.4 . . ?
C3A C2A H2A 113.4 . . ?
O1A C2A H2B 113.4 . . ?
C3A C2A H2B 113.4 . . ?
H2A C2A H2B 110.7 . . ?
N2A C3A C4A 111.4(4) . . ?
N2A C3A C2A 112.2(5) . . ?
C4A C3A C2A 114.0(6) . . ?
N2A C3A C1A 115.0(6) . . ?
C4A C3A C1A 117.1(7) . . ?
C2A C3A C1A 84.9(5) . . ?
N1A C4A C3A 113.4(4) . . ?
N1A C4A H6A 108.9 . . ?
C3A C4A H6A 108.9 . . ?
N1A C4A H6B 108.9 . . ?
C3A C4A H6B 108.9 . . ?
H6A C4A H6B 107.7 . . ?
N3A C5A N2A 110.1(4) . . ?
N3A C5A H5A 126(3) . . ?
N2A C5A H5A 124(3) . . ?
C2A O1A C1A 91.0(6) . . ?
O3A N1A O2A 126.4(5) . . ?
O3A N1A C4A 118.1(3) . . ?
O2A N1A C4A 115.4(4) . . ?
C5A N2A N5A 108.8(3) . . ?
C5A N2A C3A 133.5(4) . . ?
N5A N2A C3A 117.5(3) . . ?
N4A N5A N2A 100.7(3) . . ?
N5A N4A N3A 113.9(4) . . ?
C5A N3A N4A 106.1(4) . . ?
O1B C1B C3B 90.6(9) . . ?
O1B C1B H1C 113.5 . . ?
C3B C1B H1C 113.5 . . ?
O1B C1B H1D 113.5 . . ?
C3B C1B H1D 113.5 . . ?
H1C C1B H1D 110.8 . . ?
O1B C2B C3B 89.3(9) . . ?
O1B C2B H2C 113.8 . . ?
C3B C2B H2C 113.8 . . ?
O1B C2B H2D 113.8 . . ?
C3B C2B H2D 113.8 . . ?
H2C C2B H2D 111.0 . . ?
N2B C3B C1B 112.9(9) . . ?
N2B C3B C2B 116.0(10) . . ?
C1B C3B C2B 84.2(9) . . ?
N2B C3B C4B 110.6(7) . . ?
C1B C3B C4B 111.3(10) . . ?
C2B C3B C4B 119.2(10) . . ?
N1B C4B C3B 114.1(6) . . ?
N1B C4B H6C 108.7 . . ?
C3B C4B H6C 108.7 . . ?
N1B C4B H6D 108.7 . . ?
C3B C4B H6D 108.7 . . ?
H6C C4B H6D 107.6 . . ?
N2B C5B N3B 107.7(6) . . ?
N2B C5B H5B 126.2 . . ?
N3B C5B H5B 126.2 . . ?
C2B O1B C1B 91.5(9) . . ?
O3B N1B O2B 127.2(9) . . ?
O3B N1B C4B 115.0(6) . . ?
O2B N1B C4B 117.6(8) . . ?
C5B N2B C3B 128.9(7) . . ?
C5B N2B N5B 116.6(5) . . ?
C3B N2B N5B 114.4(6) . . ?
N4B N5B N2B 92.1(4) . . ?
N4B N3B C5B 103.8(7) . . ?
N3B N4B N5B 119.0(7) . . ?

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
O1A C2A C3A N2A -125.5(6) . . . . ?
O1A C2A C3A C4A 106.8(6) . . . . ?
O1A C2A C3A C1A -10.6(7) . . . . ?
O1A C1A C3A N2A 122.6(6) . . . . ?
O1A C1A C3A C4A -103.9(7) . . . . ?
O1A C1A C3A C2A 10.5(7) . . . . ?
N2A C3A C4A N1A 70.1(5) . . . . ?
C2A C3A C4A N1A -161.7(4) . . . . ?
C1A C3A C4A N1A -65.0(6) . . . . ?
C3A C2A O1A C1A 11.1(7) . . . . ?
C3A C1A O1A C2A -11.1(7) . . . . ?
C3A C4A N1A O3A 6.3(6) . . . . ?
C3A C4A N1A O2A -177.7(4) . . . . ?
N3A C5A N2A N5A 4.1(5) . . . . ?
N3A C5A N2A C3A 179.4(5) . . . . ?
C4A C3A N2A C5A -105.5(6) . . . . ?
C2A C3A N2A C5A 125.4(6) . . . . ?
C1A C3A N2A C5A 30.6(8) . . . . ?
C4A C3A N2A N5A 69.4(5) . . . . ?
C2A C3A N2A N5A -59.7(6) . . . . ?
C1A C3A N2A N5A -154.5(5) . . . . ?
C5A N2A N5A N4A -4.8(4) . . . . ?
C3A N2A N5A N4A 179.1(4) . . . . ?
N2A N5A N4A N3A 4.0(5) . . . . ?
N2A C5A N3A N4A -1.6(6) . . . . ?
N5A N4A N3A C5A -1.7(6) . . . . ?
O1B C1B C3B N2B -131.1(10) . . . . ?
O1B C1B C3B C2B -15.3(11) . . . . ?
O1B C1B C3B C4B 103.8(11) . . . . ?
O1B C2B C3B N2B 128.0(9) . . . . ?
O1B C2B C3B C1B 15.3(11) . . . . ?
O1B C2B C3B C4B -95.9(11) . . . . ?
N2B C3B C4B N1B 70.9(10) . . . . ?
C1B C3B C4B N1B -162.7(9) . . . . ?
C2B C3B C4B N1B -67.4(11) . . . . ?
C3B C2B O1B C1B -16.1(12) . . . . ?
C3B C1B O1B C2B 16.5(12) . . . . ?
C3B C4B N1B O3B 7.9(10) . . . . ?
C3B C4B N1B O2B -177.1(8) . . . . ?
N3B C5B N2B C3B 179.4(8) . . . . ?
N3B C5B N2B N5B 3.8(9) . . . . ?
C1B C3B N2B C5B 125.1(11) . . . . ?
C2B C3B N2B C5B 30.3(13) . . . . ?
C4B C3B N2B C5B -109.4(9) . . . . ?
C1B C3B N2B N5B -59.1(10) . . . . ?
C2B C3B N2B N5B -153.9(8) . . . . ?
C4B C3B N2B N5B 66.3(8) . . . . ?
C5B N2B N5B N4B -7.5(7) . . . . ?
C3B N2B N5B N4B 176.2(6) . . . . ?
N2B C5B N3B N4B 2.6(11) . . . . ?
C5B N3B N4B N5B -8.6(11) . . . . ?
N2B N5B N4B N3B 9.7(9) . . . . ?

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.036

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_v1_shelx
_database_code_depnum_ccdc_archive 'CCDC 2119624'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-11-01 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
5-nitro-2-(3-(nitromethyl)oxetan-3-yl)-2H-tetrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H6 N6 O5'
_chemical_formula_sum            'C5 H6 N6 O5'
_chemical_formula_weight         230.16

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.4514(5)
_cell_length_b                   7.0564(3)
_cell_length_c                   23.9816(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1768.63(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4392
_cell_measurement_theta_min      2.5640
_cell_measurement_theta_max      31.2070

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            29387
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.698
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2186
_reflns_number_gt                1751
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+0.6197P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2186
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C3 C 0.54424(12) 0.64591(19) 0.40495(6) 0.0170(3) Uani 1 1 d . . . . .
N3 N 0.59631(11) 0.70639(16) 0.35089(5) 0.0189(3) Uani 1 1 d . . . . .
O3 O 0.54203(10) 1.01532(15) 0.43796(5) 0.0266(3) Uani 1 1 d . . . . .
O2 O 0.33555(11) 1.03985(16) 0.43830(5) 0.0302(3) Uani 1 1 d . . . . .
H2B H 0.7301(17) 0.645(2) 0.4398(7) 0.023(4) Uiso 1 1 d . . . . .
H2A H 0.6241(14) 0.703(2) 0.4843(7) 0.017(4) Uiso 1 1 d . . . . .
C2 C 0.64346(14) 0.6301(2) 0.45189(6) 0.0205(3) Uani 1 1 d . . . . .
N2 N 0.54872(11) 0.64473(18) 0.30298(5) 0.0209(3) Uani 1 1 d . . . . .
O1 O 0.61399(10) 0.43050(14) 0.45944(4) 0.0243(3) Uani 1 1 d . . . . .
C1 C 0.53239(14) 0.4287(2) 0.41075(6) 0.0201(3) Uani 1 1 d . . . . .
H1B H 0.5697(15) 0.361(2) 0.3795(7) 0.023(4) Uiso 1 1 d . . . . .
H1A H 0.4463(15) 0.382(2) 0.4184(7) 0.018(4) Uiso 1 1 d . . . . .
N1 N 0.43467(12) 0.95008(17) 0.43205(5) 0.0202(3) Uani 1 1 d . . . . .
N6 N 0.61709(13) 0.7057(2) 0.20795(6) 0.0299(3) Uani 1 1 d . . . . .
N5 N 0.71534(13) 0.8396(2) 0.29124(6) 0.0285(3) Uani 1 1 d . . . . .
O5 O 0.68800(12) 0.80360(19) 0.17920(5) 0.0404(3) Uani 1 1 d . . . . .
C5 C 0.62601(13) 0.7315(2) 0.26782(6) 0.0223(3) Uani 1 1 d . . . . .
N4 N 0.69591(12) 0.82260(19) 0.34533(5) 0.0266(3) Uani 1 1 d . . . . .
O4 O 0.54055(13) 0.5890(2) 0.19060(5) 0.0407(3) Uani 1 1 d . . . . .
H4A H 0.3845(16) 0.690(2) 0.4513(7) 0.023(4) Uiso 1 1 d . . . . .
H4B H 0.3601(15) 0.738(2) 0.3876(7) 0.019(4) Uiso 1 1 d . . . . .
C4 C 0.41973(13) 0.7446(2) 0.41813(6) 0.0189(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C3 N3 1.4693(17) . ?
C3 C4 1.5093(18) . ?
C3 C2 1.5347(19) . ?
C3 C1 1.5438(19) . ?
N3 N2 1.3254(17) . ?
N3 N4 1.3318(16) . ?
O3 N1 1.2210(16) . ?
O2 N1 1.2236(16) . ?
C2 O1 1.4531(17) . ?
C2 H2B 0.956(17) . ?
C2 H2A 0.953(16) . ?
N2 C5 1.3187(18) . ?
O1 C1 1.4461(18) . ?
C1 H1B 0.971(18) . ?
C1 H1A 0.977(16) . ?
N1 C4 1.4963(18) . ?
N6 O4 1.2207(18) . ?
N6 O5 1.2256(18) . ?
N6 C5 1.4503(19) . ?
N5 N4 1.3186(18) . ?
N5 C5 1.330(2) . ?
C4 H4A 0.958(18) . ?
C4 H4B 0.963(16) . ?

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
N3 C3 C4 111.73(11) . . ?
N3 C3 C2 114.71(11) . . ?
C4 C3 C2 117.54(12) . . ?
N3 C3 C1 113.42(11) . . ?
C4 C3 C1 111.71(11) . . ?
C2 C3 C1 85.18(10) . . ?
N2 N3 N4 114.13(11) . . ?
N2 N3 C3 122.03(11) . . ?
N4 N3 C3 123.82(11) . . ?
O1 C2 C3 91.07(10) . . ?
O1 C2 H2B 110.2(10) . . ?
C3 C2 H2B 114.2(10) . . ?
O1 C2 H2A 112.1(9) . . ?
C3 C2 H2A 114.5(9) . . ?
H2B C2 H2A 112.8(14) . . ?
C5 N2 N3 99.90(12) . . ?
C1 O1 C2 91.88(10) . . ?
O1 C1 C3 90.97(10) . . ?
O1 C1 H1B 113.0(10) . . ?
C3 C1 H1B 112.8(10) . . ?
O1 C1 H1A 113.2(10) . . ?
C3 C1 H1A 115.4(9) . . ?
H1B C1 H1A 110.4(14) . . ?
O3 N1 O2 124.66(12) . . ?
O3 N1 C4 119.16(11) . . ?
O2 N1 C4 116.15(12) . . ?
O4 N6 O5 125.78(14) . . ?
O4 N6 C5 117.66(13) . . ?
O5 N6 C5 116.56(13) . . ?
N4 N5 C5 104.80(12) . . ?
N2 C5 N5 115.23(13) . . ?
N2 C5 N6 122.37(13) . . ?
N5 C5 N6 122.37(13) . . ?
N5 N4 N3 105.94(12) . . ?
N1 C4 C3 113.81(11) . . ?
N1 C4 H4A 104.3(10) . . ?
C3 C4 H4A 108.6(10) . . ?
N1 C4 H4B 106.4(9) . . ?
C3 C4 H4B 112.1(9) . . ?
H4A C4 H4B 111.3(14) . . ?

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
C4 C3 N3 N2 -76.27(16) . . . . ?
C2 C3 N3 N2 146.73(13) . . . . ?
C1 C3 N3 N2 51.07(17) . . . . ?
C4 C3 N3 N4 105.39(15) . . . . ?
C2 C3 N3 N4 -31.62(18) . . . . ?
C1 C3 N3 N4 -127.27(14) . . . . ?
N3 C3 C2 O1 -120.59(12) . . . . ?
C4 C3 C2 O1 105.01(13) . . . . ?
C1 C3 C2 O1 -6.99(10) . . . . ?
N4 N3 N2 C5 -0.08(15) . . . . ?
C3 N3 N2 C5 -178.58(12) . . . . ?
C3 C2 O1 C1 7.44(11) . . . . ?
C2 O1 C1 C3 -7.39(11) . . . . ?
N3 C3 C1 O1 121.90(12) . . . . ?
C4 C3 C1 O1 -110.75(12) . . . . ?
C2 C3 C1 O1 7.02(10) . . . . ?
N3 N2 C5 N5 -0.04(17) . . . . ?
N3 N2 C5 N6 177.86(13) . . . . ?
N4 N5 C5 N2 0.15(18) . . . . ?
N4 N5 C5 N6 -177.76(13) . . . . ?
O4 N6 C5 N2 -5.1(2) . . . . ?
O5 N6 C5 N2 175.06(14) . . . . ?
O4 N6 C5 N5 172.65(15) . . . . ?
O5 N6 C5 N5 -7.2(2) . . . . ?
C5 N5 N4 N3 -0.18(16) . . . . ?
N2 N3 N4 N5 0.18(17) . . . . ?
C3 N3 N4 N5 178.64(12) . . . . ?
O3 N1 C4 C3 -8.19(18) . . . . ?
O2 N1 C4 C3 173.89(12) . . . . ?
N3 C3 C4 N1 -71.27(15) . . . . ?
C2 C3 C4 N1 64.40(16) . . . . ?
C1 C3 C4 N1 160.46(12) . . . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.051

