#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:20:08 +0200 (lun 06 de sep de 2021) $
#$Revision: 268787 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/77/7707740.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7707740
loop_
_publ_author_name
'Gruhne, Michael S.'
'Lenz, Tobias'
'Rösch, Markus'
'Lommel, Marcus'
'Wurzenberger, Maximilian H. H.'
'Klapötke, Thomas M'
'Stierstorfer, Jörg'
_publ_section_title
;
 Nitratoethyl-5H-tetrazoles: improving the oxygen balance through
 application of organic nitrates in energetic coordination compounds.
;
_journal_issue                   31
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10811
_journal_page_last               10825
_journal_paper_doi               10.1039/d1dt01898a
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C3 H5 N5 O3'
_chemical_formula_sum            'C3 H5 N5 O3'
_chemical_formula_weight         159.12
_chemical_name_common            2-nitratoethyl-5H-tetrazole
_chemical_name_systematic        2-nitratoethyl-5H-tetrazole
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-05-17 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3292(8)
_cell_length_b                   14.3427(15)
_cell_length_c                   6.3485(5)
_cell_measurement_reflns_used    1838
_cell_measurement_temperature    128
_cell_measurement_theta_max      24.2450
_cell_measurement_theta_min      3.0800
_cell_volume                     667.36(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Encifer 1.5.1, CCDC 2014'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      128
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  -5.00   1.00    2.00    --  -15.43 128.00-122.69   66
  2  ω    -77.00  -6.00   1.00    2.00    --  -15.43 -57.00 150.00   71
  3  ω    -70.00  -3.00   1.00    2.00    --  -15.43 128.00 153.35   67
  4  ω    -83.00  -4.00   1.00    2.00    --  -15.43 -57.00-120.00   79
  5  ω    -85.00   4.00   1.00    2.00    --  -15.43 -37.00 -60.00   89
  6  ω     -1.00  82.00   1.00    2.00    --   16.37  37.00-180.00   83
  7  ω    -19.00  55.00   1.00    2.00    --   16.37 -99.00 120.00   74
  8  ω    -38.00  43.00   1.00    2.00    --   16.37 -77.00  30.00   81
  9  ω      1.00  84.00   1.00    2.00    --   16.37  57.00  90.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0780591000
_diffrn_orient_matrix_UB_12      -0.0289086000
_diffrn_orient_matrix_UB_13      0.0102303000
_diffrn_orient_matrix_UB_21      -0.0571479000
_diffrn_orient_matrix_UB_22      0.0398109000
_diffrn_orient_matrix_UB_23      -0.0061434000
_diffrn_orient_matrix_UB_31      -0.0039676000
_diffrn_orient_matrix_UB_32      -0.0048545000
_diffrn_orient_matrix_UB_33      -0.1110682000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9133
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.840
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.331
_exptl_crystal_size_min          0.239
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 457 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1355
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0311P)²+0.2168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0806
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1160
_reflns_number_total             1355
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt01898a2.cif
_cod_data_source_block           px360
_cod_depositor_comments
'Adding full bibliography for 7707739--7707758.cif.'
_cod_database_code               7707740
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.933
_shelx_estimated_absorpt_t_max   0.967
_olex2_submission_original_sample_id px360
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.244
_oxdiff_exptl_absorpt_empirical_full_min 0.801
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'
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 0.4666(3) 0.42661(15) 0.6151(4) 0.0238(5) Uani 1 1 d . . . . .
O3 O 0.1818(3) 0.43187(15) 0.5256(4) 0.0292(6) Uani 1 1 d . . . . .
O2 O 0.2491(3) 0.38158(17) 0.8409(4) 0.0325(6) Uani 1 1 d . . . . .
N2 N 0.8112(4) 0.35598(18) 0.4845(4) 0.0218(6) Uani 1 1 d . . . . .
N5 N 0.2840(4) 0.41155(19) 0.6663(4) 0.0248(6) Uani 1 1 d . . . . .
N3 N 0.7881(4) 0.3920(2) 0.2941(4) 0.0294(7) Uani 1 1 d . . . . .
N1 N 0.8629(4) 0.26781(19) 0.4828(5) 0.0280(6) Uani 1 1 d . . . . .
N4 N 0.8266(4) 0.3247(2) 0.1597(5) 0.0336(8) Uani 1 1 d . . . . .
C3 C 0.5952(5) 0.3901(2) 0.7694(5) 0.0227(7) Uani 1 1 d . . . . .
C2 C 0.7809(5) 0.4095(3) 0.6770(5) 0.0238(7) Uani 1 1 d . . . . .
C1 C 0.8716(5) 0.2510(3) 0.2775(5) 0.0303(8) Uani 1 1 d . . . . .
H3A H 0.568(4) 0.326(2) 0.779(5) 0.015(8) Uiso 1 1 d . . . . .
H2A H 0.873(4) 0.390(2) 0.778(5) 0.013(8) Uiso 1 1 d . . . . .
H2B H 0.803(5) 0.476(3) 0.646(5) 0.025(9) Uiso 1 1 d . . . . .
H3B H 0.591(5) 0.425(3) 0.901(6) 0.031(10) Uiso 1 1 d . . . . .
H1 H 0.909(5) 0.189(3) 0.217(5) 0.030(10) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 O1 C3 114.1(2) . . ?
N3 N2 C2 122.6(3) . . ?
N1 N2 N3 113.7(3) . . ?
N1 N2 C2 123.7(3) . . ?
O3 N5 O1 112.8(3) . . ?
O3 N5 O2 129.2(3) . . ?
O2 N5 O1 118.0(3) . . ?
N4 N3 N2 106.1(3) . . ?
N2 N1 C1 101.3(3) . . ?
N3 N4 C1 105.6(3) . . ?
O1 C3 C2 104.8(3) . . ?
O1 C3 H3A 105.0(19) . . ?
O1 C3 H3B 112(2) . . ?
C2 C3 H3A 113.2(19) . . ?
C2 C3 H3B 106(2) . . ?
H3A C3 H3B 116(3) . . ?
N2 C2 C3 111.5(3) . . ?
N2 C2 H2A 107.1(19) . . ?
N2 C2 H2B 108(2) . . ?
C3 C2 H2A 108.3(19) . . ?
C3 C2 H2B 114(2) . . ?
H2A C2 H2B 108(3) . . ?
N1 C1 N4 113.2(3) . . ?
N1 C1 H1 123.4(19) . . ?
N4 C1 H1 123.4(19) . . ?
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 N5 1.394(3) . ?
O1 C3 1.456(4) . ?
O3 N5 1.201(4) . ?
O2 N5 1.216(4) . ?
N2 N3 1.326(4) . ?
N2 N1 1.320(4) . ?
N2 C2 1.460(4) . ?
N3 N4 1.318(4) . ?
N1 C1 1.327(4) . ?
N4 C1 1.336(4) . ?
C3 C2 1.508(5) . ?
C3 H3A 0.95(3) . ?
C3 H3B 0.98(4) . ?
C2 H2A 0.97(3) . ?
C2 H2B 0.99(4) . ?
C1 H1 1.00(4) . ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
? ? ? ? ? ? ? ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C2 N2 -65.8(4) . . . . ?
N2 N3 N4 C1 -0.1(3) . . . . ?
N2 N1 C1 N4 -0.4(4) . . . . ?
N5 O1 C3 C2 177.0(2) . . . . ?
N3 N2 N1 C1 0.3(4) . . . . ?
N3 N2 C2 C3 98.3(4) . . . . ?
N3 N4 C1 N1 0.3(4) . . . . ?
N1 N2 N3 N4 -0.2(4) . . . . ?
N1 N2 C2 C3 -81.3(4) . . . . ?
C3 O1 N5 O3 -171.5(3) . . . . ?
C3 O1 N5 O2 9.2(4) . . . . ?
C2 N2 N3 N4 -179.8(3) . . . . ?
C2 N2 N1 C1 180.0(3) . . . . ?
