#------------------------------------------------------------------------------
#$Date: 2021-09-06 14:20:08 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/77/7707751.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_7707751
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 Cu2 N17 O3'
_chemical_formula_sum            'C3 H5 Cu2 N17 O3'
_chemical_formula_weight         454.32
_chemical_name_common
'2-nitratoethyl-5H-tetrazole dicopper(I)) tetrazide'
_chemical_name_systematic
'2-nitratoethyl-5H-tetrazole dicopper(I)) tetrazide'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-12-12
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-17 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.892(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7453(11)
_cell_length_b                   5.7379(4)
_cell_length_c                   16.3858(14)
_cell_measurement_reflns_used    1548
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.8170
_cell_measurement_theta_min      2.2370
_cell_volume                     1392.0(2)
_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, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00  -8.00   1.00   78.00    --  -23.84 -38.00 -60.00   83
  2  ω    -84.00  -8.00   1.00   78.00    --  -23.84 136.00 103.67   76
  3  ω    -96.00 -61.00   1.00   78.00    --  -23.84-178.00 -30.00   35
  4  ω    -75.00  32.00   1.00   78.00    --  -23.84   0.00 -30.00  107
  5  ω     62.00  97.00   1.00   78.00    --   24.62 178.00   0.00   35
  6  ω    -33.00  -4.00   1.00   78.00    --   24.62 132.00 -54.80   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0073475000
_diffrn_orient_matrix_UB_12      -0.1030289000
_diffrn_orient_matrix_UB_13      0.0205688000
_diffrn_orient_matrix_UB_21      0.0299698000
_diffrn_orient_matrix_UB_22      -0.0616038000
_diffrn_orient_matrix_UB_23      -0.0161940000
_diffrn_orient_matrix_UB_31      0.0366443000
_diffrn_orient_matrix_UB_32      0.0295573000
_diffrn_orient_matrix_UB_33      0.0378700000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_sigmaI/netI    0.1548
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9140
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.208
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95764
_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            brown
_exptl_crystal_density_diffrn    2.168
_exptl_crystal_description       platelet
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0514
_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)+(0.0380P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1971
_reflns_number_total             2839
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt01898a2.cif
_cod_data_source_block           px455
_cod_depositor_comments
'Adding full bibliography for 7707739--7707758.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7707751
_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'
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
Cu1 Cu 0.56729(4) 0.32610(11) 0.16748(4) 0.0179(2) Uani 1 1 d . . . . .
Cu2 Cu 0.52787(4) 0.78975(11) 0.06239(4) 0.01666(19) Uani 1 1 d . . . . .
N7 N 0.7178(3) 0.0200(7) 0.1924(3) 0.0169(10) Uani 1 1 d . . . . .
N15 N 0.4467(3) 1.0688(7) 0.0391(3) 0.0177(10) Uani 1 1 d . . . . .
N9 N 0.5991(3) 0.4952(7) 0.0758(3) 0.0187(10) Uani 1 1 d . . . . .
N12 N 0.4842(3) 0.6054(7) 0.1433(3) 0.0183(10) Uani 1 1 d . . . . .
N4 N 0.5215(3) 0.1768(8) 0.2528(3) 0.0256(11) Uani 1 1 d . . . . .
N10 N 0.6715(3) 0.4707(8) 0.0669(3) 0.0254(12) Uani 1 1 d . . . . .
N6 N 0.6356(3) 0.0396(7) 0.1611(3) 0.0184(11) Uani 1 1 d . . . . .
N3 N 0.4427(3) 0.2339(10) 0.2593(3) 0.0354(13) Uani 1 1 d . . . . .
N13 N 0.4204(3) 0.6553(8) 0.1653(4) 0.0329(13) Uani 1 1 d . . . . .
N16 N 0.3721(3) 1.0870(9) 0.0481(3) 0.0297(12) Uani 1 1 d . . . . .
N8 N 0.7942(3) -0.0025(8) 0.2212(3) 0.0267(12) Uani 1 1 d . . . . .
O1 O 0.3789(5) 0.4283(14) 0.4233(6) 0.107(3) Uani 1 1 d . . . . .
N2 N 0.4303(4) 0.0943(14) 0.3169(4) 0.065(2) Uani 1 1 d . . . . .
N17 N 0.3037(4) 1.1124(11) 0.0580(5) 0.059(2) Uani 1 1 d . . . . .
N14 N 0.3614(5) 0.7004(11) 0.1869(5) 0.068(2) Uani 1 1 d . . . . .
N11 N 0.7380(4) 0.4390(12) 0.0574(5) 0.064(2) Uani 1 1 d . . . . .
O2 O 0.3859(4) 0.4338(12) 0.5616(5) 0.088(2) Uani 1 1 d . . . . .
C3 C 0.3635(6) 0.1869(14) 0.4300(5) 0.064(2) Uani 1 1 d . . . . .
H3A H 0.310977 0.160775 0.446973 0.076 Uiso 1 1 calc R U . . .
H3B H 0.415505 0.112659 0.471920 0.076 Uiso 1 1 calc R U . . .
N5 N 0.3948(6) 0.5404(16) 0.5025(10) 0.115(5) Uani 1 1 d . . . . .
C1 C 0.5521(5) -0.0044(15) 0.3081(5) 0.063(3) Uani 1 1 d . . . . .
H1 H 0.606325 -0.080937 0.315839 0.075 Uiso 1 1 calc R U . . .
C2 C 0.3480(5) 0.096(2) 0.3397(5) 0.083(3) Uani 1 1 d . . . . .
H2A H 0.324441 -0.061837 0.335387 0.099 Uiso 1 1 calc R U . . .
H2B H 0.302809 0.191414 0.298264 0.099 Uiso 1 1 calc R U . . .
O3 O 0.4148(6) 0.7387(13) 0.5082(8) 0.179(5) Uani 1 1 d . . . . .
N1 N 0.4969(4) -0.0600(17) 0.3492(5) 0.099(3) Uani 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'
Cu Cu 0.3201 1.2651 '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
N4 Cu1 N6 90.72(19) . . ?
N4 Cu1 N9 173.17(18) . . ?
N6 Cu1 N9 94.81(19) . . ?
N4 Cu1 N12 96.62(19) . . ?
N6 Cu1 N12 166.37(18) . . ?
N9 Cu1 N12 77.17(18) . . ?
N12 Cu2 N9 77.64(18) . . ?
N12 Cu2 N15 102.05(18) . . ?
N9 Cu2 N15 174.19(17) . . ?
N12 Cu2 N15 167.46(17) . 3_675 ?
N9 Cu2 N15 99.80(19) . 3_675 ?
N15 Cu2 N15 79.2(2) . 3_675 ?
N12 Cu2 N6 101.24(17) . 1_565 ?
N9 Cu2 N6 100.99(16) . 1_565 ?
N15 Cu2 N6 84.79(16) . 1_565 ?
N15 Cu2 N6 91.29(16) 3_675 1_565 ?
N8 N7 N6 178.8(5) . . ?
N16 N15 Cu2 128.0(4) . . ?
N16 N15 Cu2 121.9(4) . 3_675 ?
Cu2 N15 Cu2 100.8(2) . 3_675 ?
N10 N9 Cu1 121.7(4) . . ?
N10 N9 Cu2 127.1(4) . . ?
Cu1 N9 Cu2 102.7(2) . . ?
N13 N12 Cu2 125.6(4) . . ?
N13 N12 Cu1 132.5(4) . . ?
Cu2 N12 Cu1 101.8(2) . . ?
N3 N4 C1 105.4(5) . . ?
N3 N4 Cu1 121.9(4) . . ?
C1 N4 Cu1 132.4(5) . . ?
N11 N10 N9 177.2(7) . . ?
N7 N6 Cu1 124.7(3) . . ?
N7 N6 Cu2 129.4(3) . 1_545 ?
Cu1 N6 Cu2 105.08(18) . 1_545 ?
N2 N3 N4 106.4(5) . . ?
N14 N13 N12 179.1(7) . . ?
N17 N16 N15 177.3(7) . . ?
N5 O1 C3 111.2(8) . . ?
N3 N2 N1 113.8(6) . . ?
N3 N2 C2 123.0(7) . . ?
N1 N2 C2 123.0(7) . . ?
O1 C3 C2 103.8(7) . . ?
O1 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
O1 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
O3 N5 O2 122.2(16) . . ?
O3 N5 O1 118.7(13) . . ?
O2 N5 O1 119.1(9) . . ?
N1 C1 N4 112.7(7) . . ?
N1 C1 H1 123.7 . . ?
N4 C1 H1 123.7 . . ?
N2 C2 C3 112.9(7) . . ?
N2 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
N2 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C1 N1 N2 101.7(6) . . ?
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
Cu1 N4 1.973(5) . ?
Cu1 N6 1.987(4) . ?
Cu1 N9 1.991(5) . ?
Cu1 N12 2.021(4) . ?
Cu2 N12 1.992(4) . ?
Cu2 N9 1.999(4) . ?
Cu2 N15 2.002(4) . ?
Cu2 N15 2.010(5) 3_675 ?
Cu2 N6 2.384(4) 1_565 ?
N7 N8 1.140(6) . ?
N7 N6 1.224(5) . ?
N15 N16 1.237(6) . ?
N9 N10 1.205(6) . ?
N12 N13 1.210(6) . ?
N4 N3 1.322(6) . ?
N4 C1 1.355(8) . ?
N10 N11 1.126(7) . ?
N3 N2 1.302(8) . ?
N13 N14 1.132(7) . ?
N16 N17 1.152(7) . ?
O1 N5 1.392(14) . ?
O1 C3 1.417(10) . ?
N2 N1 1.336(9) . ?
N2 C2 1.467(9) . ?
O2 N5 1.193(12) . ?
C3 C2 1.508(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N5 O3 1.176(11) . ?
C1 N1 1.307(9) . ?
C1 H1 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
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
C3 H3B O3 0.97 2.23 2.864(11) 122.2 1_545
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
C1 N4 N3 N2 1.2(8) . . . . ?
Cu1 N4 N3 N2 175.9(4) . . . . ?
N4 N3 N2 N1 -1.2(9) . . . . ?
N4 N3 N2 C2 -177.2(7) . . . . ?
N5 O1 C3 C2 -179.9(7) . . . . ?
C3 O1 N5 O3 174.9(8) . . . . ?
C3 O1 N5 O2 -6.6(12) . . . . ?
N3 N4 C1 N1 -0.9(10) . . . . ?
Cu1 N4 C1 N1 -174.8(6) . . . . ?
N3 N2 C2 C3 -110.5(9) . . . . ?
N1 N2 C2 C3 73.9(12) . . . . ?
O1 C3 C2 N2 70.6(9) . . . . ?
N4 C1 N1 N2 0.2(11) . . . . ?
N3 N2 N1 C1 0.6(11) . . . . ?
C2 N2 N1 C1 176.6(9) . . . . ?
