#------------------------------------------------------------------------------
#$Date: 2021-09-06 14:20:08 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/77/7707752.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_7707752
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         'C6 H10 Cu2 N22 O6'
_chemical_formula_sum            'C6 H10 Cu2 N22 O6'
_chemical_formula_weight         613.44
_chemical_name_common
'1-nitratoethyl-5H-tetrazole diazido copper(II)'
_chemical_name_systematic
'1-nitratoethyl-5H-tetrazole diazido copper(II)'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-17 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                102.119(3)
_cell_angle_beta                 96.226(3)
_cell_angle_gamma                91.774(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2622(4)
_cell_length_b                   10.5985(8)
_cell_length_c                   15.9381(14)
_cell_measurement_reflns_used    6258
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.63
_cell_volume                     1026.56(14)
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_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      173.0
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11434
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         1.968
_diffrn_source                   'rotating anode generator'
_exptl_absorpt_coefficient_mu    2.155
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.8073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.985
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0397
_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)+(0.0158P)²+1.2343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0789
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3184
_reflns_number_total             4172
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt01898a2.cif
_cod_data_source_block           yv690
_cod_depositor_comments
'Adding full bibliography for 7707739--7707758.cif.'
_cod_database_code               7707752
_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.
;
_olex2_submission_original_sample_id yv690
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cu2 Cu 0.95279(6) 0.85403(4) 0.46179(3) 0.01708(12) Uani 1 1 d . . . . .
Cu1 Cu 0.47206(6) 0.64546(4) 0.54008(3) 0.01721(12) Uani 1 1 d . . . . .
N4 N 0.5364(4) 0.7561(3) 0.65853(18) 0.0186(6) Uani 1 1 d . . . . .
N15 N 0.4400(4) 0.8389(3) 0.44925(19) 0.0197(6) Uani 1 1 d . . . . .
N9 N 0.9280(4) 0.7423(3) 0.34270(18) 0.0197(6) Uani 1 1 d . . . . .
N20 N 1.0288(4) 1.0174(3) 0.42526(18) 0.0185(6) Uani 1 1 d . . . . .
N11 N 0.4231(5) 0.5179(3) 0.42827(19) 0.0220(7) Uani 1 1 d . . . . .
N17 N 0.8381(4) 0.7110(3) 0.51037(19) 0.0190(6) Uani 1 1 d . . . . .
N12 N 0.3694(4) 0.5459(3) 0.3592(2) 0.0208(6) Uani 1 1 d . . . . .
N18 N 0.9672(4) 0.6576(3) 0.55121(19) 0.0189(6) Uani 1 1 d . . . . .
N1 N 0.6366(4) 0.9081(3) 0.76836(19) 0.0228(7) Uani 1 1 d . . . . .
N14 N 0.3340(4) 0.7885(3) 0.49332(19) 0.0197(6) Uani 1 1 d . . . . .
N8 N 0.9880(5) 0.7824(3) 0.2726(2) 0.0272(7) Uani 1 1 d . . . . .
N3 N 0.5102(5) 0.7135(3) 0.7319(2) 0.0336(8) Uani 1 1 d . . . . .
N19 N 1.0853(5) 0.6050(3) 0.5905(2) 0.0316(8) Uani 1 1 d . . . . .
N6 N 0.8352(4) 0.5955(3) 0.22920(19) 0.0222(7) Uani 1 1 d . . . . .
N21 N 0.9423(4) 1.0502(3) 0.3610(2) 0.0215(7) Uani 1 1 d . . . . .
N7 N 0.9329(5) 0.6946(3) 0.2044(2) 0.0294(7) Uani 1 1 d . . . . .
N22 N 0.8730(5) 1.0830(3) 0.3008(2) 0.0351(8) Uani 1 1 d . . . . .
N2 N 0.5699(6) 0.8050(3) 0.7982(2) 0.0367(8) Uani 1 1 d . . . . .
N16 N 0.5372(5) 0.8901(3) 0.4078(2) 0.0337(8) Uani 1 1 d . . . . .
N13 N 0.3220(6) 0.5755(3) 0.2951(2) 0.0396(9) Uani 1 1 d . . . . .
O1 O 0.3671(5) 1.0998(3) 0.8583(2) 0.0523(9) Uani 1 1 d . . . . .
O4 O 1.0973(5) 0.3934(3) 0.1388(2) 0.0508(8) Uani 1 1 d . . . . .
C4 C 0.8360(5) 0.6267(3) 0.3137(2) 0.0218(8) Uani 1 1 d . . . . .
H4 H 0.778808 0.573641 0.348020 0.026 Uiso 1 1 calc R U . . .
C1 C 0.6101(5) 0.8760(3) 0.6829(2) 0.0210(8) Uani 1 1 d . . . . .
H1 H 0.640005 0.931418 0.645371 0.025 Uiso 1 1 calc R U . . .
O3 O 0.5368(6) 1.1458(5) 0.9916(2) 0.0843(13) Uani 1 1 d . . . . .
C2 C 0.7225(6) 1.0275(4) 0.8277(3) 0.0341(10) Uani 1 1 d . . . . .
H2A H 0.858480 1.056405 0.809389 0.041 Uiso 1 1 calc R U . . .
H2B H 0.755256 1.010740 0.886461 0.041 Uiso 1 1 calc R U . . .
O6 O 0.9366(7) 0.3511(5) 0.0045(2) 0.0883(14) Uani 1 1 d . . . . .
C5 C 0.7470(6) 0.4795(4) 0.1662(3) 0.0347(10) Uani 1 1 d . . . . .
H5A H 0.727032 0.499591 0.108050 0.042 Uiso 1 1 calc R U . . .
H5B H 0.604039 0.454349 0.180532 0.042 Uiso 1 1 calc R U . . .
O2 O 0.1975(6) 1.0867(5) 0.9675(3) 0.0978(16) Uani 1 1 d . . . . .
N5 N 0.3696(8) 1.1131(5) 0.9469(3) 0.0661(13) Uani 1 1 d . . . . .
O5 O 1.2813(6) 0.3990(5) 0.0321(3) 0.0891(14) Uani 1 1 d . . . . .
C6 C 0.8887(8) 0.3685(4) 0.1643(3) 0.0460(12) Uani 1 1 d . . . . .
H6A H 0.908067 0.348326 0.222507 0.055 Uiso 1 1 calc R U . . .
H6B H 0.816807 0.291606 0.123602 0.055 Uiso 1 1 calc R U . . .
C3 C 0.5668(8) 1.1331(4) 0.8305(3) 0.0489(12) Uani 1 1 d . . . . .
H3A H 0.632927 1.212517 0.870331 0.059 Uiso 1 1 calc R U . . .
H3B H 0.538765 1.152006 0.772213 0.059 Uiso 1 1 calc R U . . .
N10 N 1.1038(8) 0.3790(5) 0.0506(3) 0.0665(13) 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
N9 Cu2 N20 173.60(11) . 2_776 ?
N9 Cu2 N16 80.69(11) . . ?
N20 Cu2 N9 95.15(11) . . ?
N20 Cu2 N20 78.98(12) . 2_776 ?
N20 Cu2 N16 96.32(11) 2_776 . ?
N20 Cu2 N16 86.85(10) . . ?
N17 Cu2 N9 92.07(12) . . ?
N17 Cu2 N20 93.41(11) . 2_776 ?
N17 Cu2 N20 169.31(12) . . ?
N17 Cu2 N16 86.55(10) . . ?
N4 Cu1 N11 95.85(11) . 2_666 ?
N4 Cu1 N14 92.49(11) . . ?
N11 Cu1 N4 172.96(11) . . ?
N11 Cu1 N11 77.11(13) . 2_666 ?
N11 Cu1 N14 94.54(12) . . ?
N14 Cu1 N11 170.44(12) . 2_666 ?
N3 N4 Cu1 123.4(2) . . ?
C1 N4 Cu1 129.9(2) . . ?
C1 N4 N3 106.7(3) . . ?
N16 N15 N14 177.9(3) . . ?
N8 N9 Cu2 124.1(2) . . ?
C4 N9 Cu2 129.4(2) . . ?
C4 N9 N8 106.2(3) . . ?
Cu2 N20 Cu2 101.02(12) . 2_776 ?
N21 N20 Cu2 117.4(2) . 2_776 ?
N21 N20 Cu2 124.8(2) . . ?
Cu1 N11 Cu1 102.89(13) . 2_666 ?
N12 N11 Cu1 132.4(2) . 2_666 ?
N12 N11 Cu1 124.0(2) . . ?
N18 N17 Cu2 116.9(2) . . ?
N13 N12 N11 178.1(4) . . ?
N19 N18 N17 178.2(3) . . ?
N2 N1 C2 121.0(3) . . ?
C1 N1 N2 107.8(3) . . ?
C1 N1 C2 131.1(3) . . ?
N15 N14 Cu1 115.4(2) . . ?
N7 N8 N9 109.7(3) . . ?
N2 N3 N4 109.2(3) . . ?
N7 N6 C5 121.4(3) . . ?
C4 N6 N7 108.0(3) . . ?
C4 N6 C5 130.7(3) . . ?
N22 N21 N20 176.2(4) . . ?
N8 N7 N6 107.1(3) . . ?
N3 N2 N1 107.2(3) . . ?
N15 N16 Cu2 103.9(2) . . ?
N5 O1 C3 115.2(4) . . ?
N10 O4 C6 115.4(3) . . ?
N9 C4 N6 109.0(3) . . ?
N9 C4 H4 125.5 . . ?
N6 C4 H4 125.5 . . ?
N4 C1 N1 108.9(3) . . ?
N4 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
N1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
N1 C2 C3 111.8(3) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
N6 C5 H5A 109.1 . . ?
N6 C5 H5B 109.1 . . ?
N6 C5 C6 112.6(3) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
O3 N5 O1 118.0(5) . . ?
O3 N5 O2 129.1(5) . . ?
O2 N5 O1 112.9(4) . . ?
O4 C6 C5 113.1(4) . . ?
O4 C6 H6A 109.0 . . ?
O4 C6 H6B 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
O1 C3 C2 112.7(4) . . ?
O1 C3 H3A 109.1 . . ?
O1 C3 H3B 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
O6 N10 O4 117.2(5) . . ?
O6 N10 O5 129.6(5) . . ?
O5 N10 O4 113.1(4) . . ?
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
Cu2 N9 2.002(3) . ?
Cu2 N20 1.999(3) . ?
Cu2 N20 2.007(3) 2_776 ?
Cu2 N17 1.990(3) . ?
Cu2 N16 2.715(3) . ?
Cu1 N4 1.994(3) . ?
Cu1 N11 2.012(3) 2_666 ?
Cu1 N11 1.986(3) . ?
Cu1 N14 2.004(3) . ?
N4 N3 1.363(4) . ?
N4 C1 1.302(4) . ?
N15 N14 1.207(4) . ?
N15 N16 1.149(4) . ?
N9 N8 1.361(4) . ?
N9 C4 1.308(4) . ?
N20 N21 1.227(4) . ?
N11 N12 1.215(4) . ?
N17 N18 1.211(4) . ?
N12 N13 1.142(4) . ?
N18 N19 1.150(4) . ?
N1 N2 1.351(4) . ?
N1 C1 1.324(4) . ?
N1 C2 1.460(4) . ?
N8 N7 1.281(4) . ?
N3 N2 1.287(4) . ?
N6 N7 1.350(4) . ?
N6 C4 1.317(4) . ?
N6 C5 1.464(4) . ?
N21 N22 1.135(4) . ?
O1 N5 1.388(5) . ?
O1 C3 1.430(6) . ?
O4 C6 1.443(5) . ?
O4 N10 1.387(5) . ?
C4 H4 0.9500 . ?
C1 H1 0.9500 . ?
O3 N5 1.198(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.503(6) . ?
O6 N10 1.202(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.493(6) . ?
O2 N5 1.201(5) . ?
O5 N10 1.204(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
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
Cu2 N9 N8 N7 -173.4(2) . . . . ?
Cu2 N9 C4 N6 172.6(2) . . . . ?
Cu1 N4 N3 N2 178.3(2) . . . . ?
Cu1 N4 C1 N1 -177.4(2) . . . . ?
N4 N3 N2 N1 -0.3(4) . . . . ?
N9 N8 N7 N6 0.1(4) . . . . ?
N1 C2 C3 O1 60.1(5) . . . . ?
N8 N9 C4 N6 -0.7(4) . . . . ?
N3 N4 C1 N1 1.8(4) . . . . ?
N6 C5 C6 O4 -62.3(5) . . . . ?
N7 N6 C4 N9 0.8(4) . . . . ?
N7 N6 C5 C6 102.2(4) . . . . ?
N2 N1 C1 N4 -2.1(4) . . . . ?
N2 N1 C2 C3 -107.0(4) . . . . ?
C4 N9 N8 N7 0.4(4) . . . . ?
C4 N6 N7 N8 -0.5(4) . . . . ?
C4 N6 C5 C6 -79.0(5) . . . . ?
C1 N4 N3 N2 -1.0(4) . . . . ?
C1 N1 N2 N3 1.4(4) . . . . ?
C1 N1 C2 C3 74.0(5) . . . . ?
C2 N1 N2 N3 -177.8(3) . . . . ?
C2 N1 C1 N4 177.1(3) . . . . ?
C5 N6 N7 N8 178.5(3) . . . . ?
C5 N6 C4 N9 -178.1(3) . . . . ?
N5 O1 C3 C2 79.5(4) . . . . ?
C6 O4 N10 O6 2.0(6) . . . . ?
C6 O4 N10 O5 -179.0(4) . . . . ?
C3 O1 N5 O3 -2.8(7) . . . . ?
C3 O1 N5 O2 178.5(4) . . . . ?
N10 O4 C6 C5 -80.1(4) . . . . ?
