#------------------------------------------------------------------------------
#$Date: 2019-11-24 08:16:52 +0100 (dom 24 de nov de 2019) $
#$Revision: 237434 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/71/7237128.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_7237128
loop_
_publ_author_name
'Szimhardt, Norbert'
'Wurzenberger, Maximilian H. H.'
'Klapötke, Thomas M.'
'Lechner, Jasmin T.'
'Reichherzer, Hannes'
'Unger, Cornelia C.'
'Stierstorfer, Jörg'
_publ_section_title
;
 Highly functional energetic complexes: stability tuning through
 coordination diversity of isomeric propyl-linked ditetrazoles
;
_journal_issue                   15
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              6565
_journal_paper_doi               10.1039/C8TA01412D
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C10 H20 Cu N16 O2, 2(C2 N3 O4)'
_chemical_formula_sum            'C14 H20 Cu N22 O10'
_chemical_formula_weight         720.06
_chemical_name_common
'diaqua bis(di(5H-tetrazol1-yl)propyl) copper(II) cyanodinitromethanide'
_chemical_name_systematic
;
diaqua bis(di(5H-tetrazol1-yl)propyl) copper(II) cyanodinitromethanide'
;
_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   mixed
_audit_creation_date
;
'Thu Jul 07 17:22:40 2016'
;
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-01-12 deposited with the CCDC.
2018-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.390(4)
_cell_angle_beta                 92.808(4)
_cell_angle_gamma                98.412(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4670(5)
_cell_length_b                   10.3140(5)
_cell_length_c                   14.0761(7)
_cell_measurement_reflns_used    4484
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      32.1440
_cell_measurement_theta_min      4.2210
_cell_volume                     1357.87(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00  105.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   19.0000    0.0000 117

#__ type_ start__ end____ width___ exp.time_
  2 omega   19.00   45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   57.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   55.00   81.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   57.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   45.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  179.0000 -180.0000 65

#__ type_ start__ end____ width___ exp.time_
  5 omega  -12.00   42.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994   77.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
  6 omega   18.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000  -30.0000 57

#__ type_ start__ end____ width___ exp.time_
  7 omega   -8.00   63.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000 -180.0000 71

#__ type_ start__ end____ width___ exp.time_
  8 omega  -90.00  -14.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  -77.0000 -120.0000 76

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0630605000
_diffrn_orient_matrix_UB_12      0.0292257000
_diffrn_orient_matrix_UB_13      0.0025225000
_diffrn_orient_matrix_UB_21      -0.0355203000
_diffrn_orient_matrix_UB_22      -0.0465062000
_diffrn_orient_matrix_UB_23      -0.0337663000
_diffrn_orient_matrix_UB_31      -0.0226423000
_diffrn_orient_matrix_UB_32      -0.0426239000
_diffrn_orient_matrix_UB_33      0.0374069000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11012
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         4.231
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_description       block
_exptl_crystal_F_000             734
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         5316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0293
_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)+(0.0266P)²+1.0037P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4536
_reflns_number_total             5316
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ta01412d2.cif
_cod_data_source_block           lx333
_cod_database_code               7237128
_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   0.614
_shelx_estimated_absorpt_t_max   0.787
_shelxl_version_number           2013-4
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
Cu1 Cu 0.5000 0.5000 0.5000 0.01140(9) Uani 1 2 d S . P
O1 O 0.73326(15) 0.48232(16) 0.55320(11) 0.0162(3) Uani 1 1 d . . .
N1 N 0.55760(16) 0.63035(14) 0.39829(11) 0.0132(3) Uani 1 1 d . . .
N2 N 0.69538(17) 0.66800(16) 0.37644(12) 0.0186(4) Uani 1 1 d . . .
N3 N 0.69972(17) 0.74649(16) 0.30544(12) 0.0192(4) Uani 1 1 d . . .
N4 N 0.56432(16) 0.76098(14) 0.28051(11) 0.0119(3) Uani 1 1 d . . .
N5 N 0.50480(16) 0.35081(14) 0.40660(11) 0.0126(3) Uani 1 1 d . . .
N6 N 0.60213(18) 0.36032(16) 0.33790(12) 0.0195(4) Uani 1 1 d . . .
N7 N 0.59607(19) 0.24912(16) 0.29431(13) 0.0210(4) Uani 1 1 d . . .
N8 N 0.49403(16) 0.16546(14) 0.33480(11) 0.0129(3) Uani 1 1 d . . .
C1 C 0.4784(2) 0.68941(17) 0.33762(14) 0.0145(4) Uani 1 1 d . . .
H1 H 0.3770 0.6818 0.3353 0.017 Uiso 1 1 calc R U .
C2 C 0.4392(2) 0.22859(18) 0.40302(14) 0.0141(4) Uani 1 1 d . . .
H2 H 0.3654 0.1922 0.4425 0.017 Uiso 1 1 calc R U .
C3 C 0.4557(2) 0.02798(18) 0.30223(15) 0.0170(4) Uani 1 1 d . . .
H3A H 0.3623(15) 0.0162(3) 0.2712(5) 0.020 Uiso 1 1 calc R U .
H3B H 0.4534(2) -0.0286(9) 0.3560(9) 0.020 Uiso 1 1 calc R U .
C4 C 0.5628(2) -0.00848(18) 0.23398(14) 0.0163(4) Uani 1 1 d . . .
H4A H 0.6538(15) 0.0086(3) 0.2631(5) 0.020 Uiso 1 1 calc R U .
H4B H 0.5611(2) 0.0439(9) 0.1807(9) 0.020 Uiso 1 1 calc R U .
C5 C 0.5336(2) 0.84823(18) 0.20242(13) 0.0143(4) Uani 1 1 d . . .
H5A H 0.4371(16) 0.8271(4) 0.1810(4) 0.017 Uiso 1 1 calc R U .
H5B H 0.5907(9) 0.8352(3) 0.1512(8) 0.017 Uiso 1 1 calc R U .
Cu2 Cu 0.0000 0.0000 0.0000 0.01163(9) Uani 1 2 d S . P
O2 O -0.24737(16) -0.08231(16) 0.01531(11) 0.0186(3) Uani 1 1 d . . .
N9 N 0.01718(17) 0.32791(14) 0.16903(11) 0.0135(3) Uani 1 1 d . . .
N10 N -0.06773(18) 0.23943(15) 0.21902(12) 0.0189(4) Uani 1 1 d . . .
N11 N -0.08663(18) 0.13154(16) 0.17024(12) 0.0179(4) Uani 1 1 d . . .
N12 N -0.01428(17) 0.14859(15) 0.08893(11) 0.0134(3) Uani 1 1 d . . .
N13 N 0.04355(16) -0.11325(14) 0.11153(11) 0.0125(3) Uani 1 1 d . . .
N14 N 0.17960(18) -0.11399(17) 0.14525(13) 0.0218(4) Uani 1 1 d . . .
N15 N 0.18124(18) -0.19847(17) 0.21239(12) 0.0199(4) Uani 1 1 d . . .
N16 N 0.04590(16) -0.25339(14) 0.22268(11) 0.0110(3) Uani 1 1 d . . .
C6 C 0.0697(2) 0.45990(18) 0.20731(15) 0.0168(4) Uani 1 1 d . . .
H6A H 0.0996(6) 0.5154(9) 0.1573(8) 0.020 Uiso 1 1 calc R U .
H6B H 0.1490(13) 0.45633(18) 0.2494(7) 0.020 Uiso 1 1 calc R U .
C7 C 0.0489(2) 0.27164(18) 0.09005(14) 0.0144(4) Uani 1 1 d . . .
H7 H 0.1069 0.3124 0.0423 0.017 Uiso 1 1 calc R U .
C8 C -0.0375(2) -0.19935(18) 0.16098(13) 0.0146(4) Uani 1 1 d . . .
H8 H -0.1386 -0.2195 0.1538 0.018 Uiso 1 1 calc R U .
C9 C 0.0117(2) -0.34813(17) 0.29868(13) 0.0126(4) Uani 1 1 d . . .
H9A H -0.0597(11) -0.3184(5) 0.3378(6) 0.015 Uiso 1 1 calc R U .
H9B H 0.0974(13) -0.35218(18) 0.3391(6) 0.015 Uiso 1 1 calc R U .
C10 C -0.0448(2) 0.51595(17) 0.25902(14) 0.0138(4) Uani 1 1 d . . .
H10A H -0.0759(5) 0.4592(9) 0.3101(8) 0.017 Uiso 1 1 calc R U .
H10B H -0.1257(13) 0.52052(18) 0.2159(7) 0.017 Uiso 1 1 calc R U .
O3 O 0.80115(17) 0.46742(17) 0.02797(12) 0.0369(4) Uani 1 1 d . . .
O4 O 0.6761(2) 0.60776(15) 0.08449(14) 0.0433(5) Uani 1 1 d . . .
O5 O 0.37535(17) 0.29267(17) 0.12982(12) 0.0335(4) Uani 1 1 d . . .
O6 O 0.4314(2) 0.50401(17) 0.15258(13) 0.0406(4) Uani 1 1 d . . .
N17 N 0.6901(2) 0.49357(18) 0.06390(14) 0.0279(4) Uani 1 1 d . . .
N18 N 0.4587(2) 0.39830(18) 0.12277(13) 0.0254(4) Uani 1 1 d . . .
N19 N 0.6238(2) 0.16091(19) 0.02362(14) 0.0299(4) Uani 1 1 d . . .
C11 C 0.5859(2) 0.38814(19) 0.07886(14) 0.0183(4) Uani 1 1 d . . .
C12 C 0.6084(2) 0.2632(2) 0.04828(15) 0.0215(4) Uani 1 1 d . . .
O7 O 0.95258(15) 0.35719(13) 0.47265(10) 0.0196(3) Uani 1 1 d . . .
O8 O 1.11414(15) 0.26107(14) 0.40833(11) 0.0231(3) Uani 1 1 d . . .
O9 O 0.72326(15) 0.19765(14) 0.51868(11) 0.0227(3) Uani 1 1 d . . .
O10 O 0.70886(16) -0.00189(14) 0.46413(11) 0.0257(3) Uani 1 1 d . . .
N20 N 0.99200(17) 0.25719(15) 0.44008(11) 0.0148(3) Uani 1 1 d . . .
N21 N 0.77361(18) 0.11230(16) 0.47471(12) 0.0178(4) Uani 1 1 d . . .
N22 N 1.0117(2) -0.05148(18) 0.36009(14) 0.0303(5) Uani 1 1 d . . .
C13 C 0.9054(2) 0.13690(18) 0.43384(13) 0.0146(4) Uani 1 1 d . . .
C14 C 0.9620(2) 0.03224(19) 0.39255(14) 0.0192(4) Uani 1 1 d . . .
H1A H 0.771(3) 0.436(2) 0.5216(18) 0.024(7) Uiso 1 1 d . . .
H1B H 0.784(3) 0.552(3) 0.5553(18) 0.027(7) Uiso 1 1 d . . .
H2A H -0.292(3) -0.132(3) -0.020(2) 0.034(8) Uiso 1 1 d . . .
H2B H -0.280(3) -0.019(3) 0.015(2) 0.040(8) 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'
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'
H H 0.0000 0.0000 '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
N1 Cu1 N1 180.0 2_666 .
N1 Cu1 N5 89.82(6) 2_666 .
N1 Cu1 N5 90.18(6) . .
N1 Cu1 N5 90.18(6) 2_666 2_666
N1 Cu1 N5 89.82(6) . 2_666
N5 Cu1 N5 180.00(7) . 2_666
N1 Cu1 O1 94.98(6) 2_666 2_666
N1 Cu1 O1 85.02(6) . 2_666
N5 Cu1 O1 90.51(6) . 2_666
N5 Cu1 O1 89.49(6) 2_666 2_666
N1 Cu1 O1 85.02(6) 2_666 .
N1 Cu1 O1 94.98(6) . .
N5 Cu1 O1 89.49(6) . .
N5 Cu1 O1 90.50(6) 2_666 .
O1 Cu1 O1 180.0 2_666 .
Cu1 O1 H1A 113.8(18) . .
Cu1 O1 H1B 112.4(17) . .
H1A O1 H1B 106(2) . .
C1 N1 N2 106.42(15) . .
C1 N1 Cu1 130.29(13) . .
N2 N1 Cu1 123.18(12) . .
N3 N2 N1 109.63(15) . .
N2 N3 N4 107.18(15) . .
C1 N4 N3 108.52(15) . .
C1 N4 C5 131.10(16) . .
N3 N4 C5 120.36(15) . .
C2 N5 N6 106.26(15) . .
C2 N5 Cu1 132.17(13) . .
N6 N5 Cu1 121.02(12) . .
N7 N6 N5 110.01(15) . .
N6 N7 N8 106.69(15) . .
C2 N8 N7 108.82(15) . .
C2 N8 C3 129.05(16) . .
N7 N8 C3 122.12(15) . .
N1 C1 N4 108.25(17) . .
N1 C1 H1 125.9 . .
N4 C1 H1 125.9 . .
N5 C2 N8 108.21(16) . .
N5 C2 H2 125.9 . .
N8 C2 H2 125.9 . .
N8 C3 C4 110.71(16) . .
N8 C3 H3A 109.5 . .
C4 C3 H3A 109.5 . .
N8 C3 H3B 109.5 . .
C4 C3 H3B 109.5 . .
H3A C3 H3B 108.1 . .
C3 C4 C5 113.07(16) . 1_545
C3 C4 H4A 109.0 . .
C5 C4 H4A 109.0 1_545 .
C3 C4 H4B 109.0 . .
C5 C4 H4B 109.0 1_545 .
H4A C4 H4B 107.8 . .
N4 C5 C4 111.42(16) . 1_565
N4 C5 H5A 109.3 . .
C4 C5 H5A 109.3 1_565 .
N4 C5 H5B 109.3 . .
C4 C5 H5B 109.3 1_565 .
H5A C5 H5B 108.0 . .
N12 Cu2 N12 180.00(9) 2 .
N12 Cu2 N13 90.25(6) 2 2
N12 Cu2 N13 89.75(6) . 2
N12 Cu2 N13 89.75(6) 2 .
N12 Cu2 N13 90.25(6) . .
N13 Cu2 N13 180.0 2 .
N12 Cu2 O2 89.32(6) 2 .
N12 Cu2 O2 90.68(6) . .
N13 Cu2 O2 92.39(6) 2 .
N13 Cu2 O2 87.61(6) . .
N12 Cu2 O2 90.68(6) 2 2
N12 Cu2 O2 89.32(6) . 2
N13 Cu2 O2 87.61(6) 2 2
N13 Cu2 O2 92.39(6) . 2
O2 Cu2 O2 180.0 . 2
Cu2 O2 H2A 124(2) . .
Cu2 O2 H2B 101(2) . .
H2A O2 H2B 109(3) . .
C7 N9 N10 109.02(15) . .
C7 N9 C6 129.30(16) . .
N10 N9 C6 121.47(16) . .
N11 N10 N9 106.75(15) . .
N10 N11 N12 109.60(15) . .
C7 N12 N11 106.64(15) . .
C7 N12 Cu2 130.92(13) . .
N11 N12 Cu2 122.11(12) . .
C8 N13 N14 106.62(15) . .
C8 N13 Cu2 132.51(13) . .
N14 N13 Cu2 120.77(12) . .
N15 N14 N13 109.49(15) . .
N14 N15 N16 107.25(15) . .
C8 N16 N15 108.27(15) . .
C8 N16 C9 131.37(16) . .
N15 N16 C9 120.15(14) . .
N9 C6 C10 111.56(16) . .
N9 C6 H6A 109.3 . .
C10 C6 H6A 109.3 . .
N9 C6 H6B 109.3 . .
C10 C6 H6B 109.3 . .
H6A C6 H6B 108.0 . .
N9 C7 N12 107.98(16) . .
N9 C7 H7 126.0 . .
N12 C7 H7 126.0 . .
N13 C8 N16 108.36(17) . .
N13 C8 H8 125.8 . .
N16 C8 H8 125.8 . .
N16 C9 C10 111.81(15) . 1_545
N16 C9 H9A 109.3 . .
C10 C9 H9A 109.3 1_545 .
N16 C9 H9B 109.3 . .
C10 C9 H9B 109.3 1_545 .
H9A C9 H9B 107.9 . .
C6 C10 C9 110.80(16) . 1_565
C6 C10 H10A 109.5 . .
C9 C10 H10A 109.5 1_565 .
C6 C10 H10B 109.5 . .
C9 C10 H10B 109.5 1_565 .
H10A C10 H10B 108.1 . .
O4 N17 O3 121.22(19) . .
O4 N17 C11 122.7(2) . .
O3 N17 C11 116.10(19) . .
O6 N18 O5 122.80(19) . .
O6 N18 C11 121.84(19) . .
O5 N18 C11 115.36(18) . .
N17 C11 N18 123.82(19) . .
N17 C11 C12 118.39(19) . .
N18 C11 C12 117.79(18) . .
N19 C12 C11 178.6(2) . .
O7 N20 O8 120.88(16) . .
O7 N20 C13 123.12(16) . .
O8 N20 C13 115.97(16) . .
O9 N21 O10 121.99(17) . .
O9 N21 C13 122.33(16) . .
O10 N21 C13 115.67(17) . .
N20 C13 N21 123.20(17) . .
N20 C13 C14 117.27(17) . .
N21 C13 C14 119.18(17) . .
N22 C14 C13 178.1(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.0106(15) 2_666
Cu1 N1 2.0106(15) .
Cu1 N5 2.0241(15) .
Cu1 N5 2.0241(15) 2_666
Cu1 O1 2.3298(14) 2_666
Cu1 O1 2.3299(14) .
O1 H1A 0.78(3) .
O1 H1B 0.81(3) .
N1 C1 1.319(2) .
N1 N2 1.356(2) .
N2 N3 1.289(2) .
N3 N4 1.342(2) .
N4 C1 1.323(2) .
N4 C5 1.470(2) .
N5 C2 1.321(2) .
N5 N6 1.362(2) .
N6 N7 1.290(2) .
N7 N8 1.349(2) .
N8 C2 1.325(2) .
N8 C3 1.475(2) .
C1 H1 0.9500 .
C2 H2 0.9500 .
C3 C4 1.515(3) .
C3 H3A 0.957(15) .
C3 H3B 0.957(15) .
C4 C5 1.522(3) 1_545
C4 H4A 0.928(15) .
C4 H4B 0.928(15) .
C5 C4 1.522(3) 1_565
C5 H5A 0.942(15) .
C5 H5B 0.942(15) .
Cu2 N12 1.9962(15) 2
Cu2 N12 1.9963(15) .
Cu2 N13 2.0252(15) 2
Cu2 N13 2.0253(15) .
Cu2 O2 2.3920(15) .
Cu2 O2 2.3920(15) 2
O2 H2A 0.77(3) .
O2 H2B 0.77(3) .
N9 C7 1.318(2) .
N9 N10 1.350(2) .
N9 C6 1.468(2) .
N10 N11 1.289(2) .
N11 N12 1.362(2) .
N12 C7 1.321(2) .
N13 C8 1.312(2) .
N13 N14 1.352(2) .
N14 N15 1.291(2) .
N15 N16 1.338(2) .
N16 C8 1.325(2) .
N16 C9 1.470(2) .
C6 C10 1.514(3) .
C6 H6A 0.939(15) .
C6 H6B 0.939(15) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 C10 1.518(2) 1_545
C9 H9A 0.974(15) .
C9 H9B 0.974(15) .
C10 C9 1.518(2) 1_565
C10 H10A 0.960(14) .
C10 H10B 0.960(14) .
O3 N17 1.252(3) .
O4 N17 1.238(2) .
O5 N18 1.256(2) .
O6 N18 1.232(2) .
N17 C11 1.382(3) .
N18 C11 1.397(3) .
N19 C12 1.140(3) .
C11 C12 1.405(3) .
O7 N20 1.239(2) .
O8 N20 1.255(2) .
O9 N21 1.237(2) .
O10 N21 1.250(2) .
N20 C13 1.383(2) .
N21 C13 1.390(3) .
N22 C14 1.144(3) .
C13 C14 1.408(3) .
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
O1 H1A O7 0.78(3) 2.15(3) 2.873(2) 154(2) .
O1 H1A O9 0.78(3) 2.43(2) 2.960(2) 126(2) .
O1 H1B O8 0.81(3) 2.07(3) 2.858(2) 165(2) 2_766
O1 H1B O7 0.81(3) 2.58(3) 3.224(2) 138(2) 2_766
O1 H1B N20 0.81(3) 2.67(3) 3.452(2) 165(2) 2_766
O2 H2A O5 0.77(3) 2.28(3) 3.046(2) 167(3) 2
O2 H2B N19 0.77(3) 2.18(3) 2.949(2) 176(3) 1_455
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_4
C1 N1 N2 N3 -0.1(2) .
Cu1 N1 N2 N3 176.51(13) .
N1 N2 N3 N4 0.2(2) .
N2 N3 N4 C1 -0.2(2) .
N2 N3 N4 C5 178.45(16) .
C2 N5 N6 N7 0.1(2) .
Cu1 N5 N6 N7 172.60(13) .
N5 N6 N7 N8 -0.1(2) .
N6 N7 N8 C2 0.1(2) .
N6 N7 N8 C3 179.24(17) .
N2 N1 C1 N4 -0.1(2) .
Cu1 N1 C1 N4 -176.31(12) .
N3 N4 C1 N1 0.2(2) .
C5 N4 C1 N1 -178.29(17) .
N6 N5 C2 N8 0.0(2) .
Cu1 N5 C2 N8 -171.33(12) .
N7 N8 C2 N5 -0.1(2) .
C3 N8 C2 N5 -179.10(17) .
C2 N8 C3 C4 -170.36(18) .
N7 N8 C3 C4 10.7(2) .
N8 C3 C4 C5 176.63(16) 1_545
C1 N4 C5 C4 101.0(2) 1_565
N3 N4 C5 C4 -77.3(2) 1_565
C7 N9 N10 N11 -0.1(2) .
C6 N9 N10 N11 -175.35(16) .
N9 N10 N11 N12 0.3(2) .
N10 N11 N12 C7 -0.3(2) .
N10 N11 N12 Cu2 173.74(12) .
C8 N13 N14 N15 0.5(2) .
Cu2 N13 N14 N15 -176.42(13) .
N13 N14 N15 N16 0.1(2) .
N14 N15 N16 C8 -0.6(2) .
N14 N15 N16 C9 -175.93(16) .
C7 N9 C6 C10 145.60(19) .
N10 N9 C6 C10 -40.2(2) .
N10 N9 C7 N12 -0.1(2) .
C6 N9 C7 N12 174.66(17) .
N11 N12 C7 N9 0.2(2) .
Cu2 N12 C7 N9 -173.09(12) .
N14 N13 C8 N16 -0.9(2) .
Cu2 N13 C8 N16 175.55(12) .
N15 N16 C8 N13 0.9(2) .
C9 N16 C8 N13 175.54(17) .
C8 N16 C9 C10 71.2(2) 1_545
N15 N16 C9 C10 -114.65(18) 1_545
N9 C6 C10 C9 179.59(15) 1_565
O4 N17 C11 N18 -3.5(3) .
O3 N17 C11 N18 176.50(19) .
O4 N17 C11 C12 176.52(19) .
O3 N17 C11 C12 -3.5(3) .
O6 N18 C11 N17 -0.9(3) .
O5 N18 C11 N17 179.41(18) .
O6 N18 C11 C12 179.16(19) .
O5 N18 C11 C12 -0.6(3) .
O7 N20 C13 N21 -8.9(3) .
O8 N20 C13 N21 172.84(17) .
O7 N20 C13 C14 178.00(17) .
O8 N20 C13 C14 -0.3(2) .
O9 N21 C13 N20 1.1(3) .
O10 N21 C13 N20 -178.94(17) .
O9 N21 C13 C14 174.14(17) .
O10 N21 C13 C14 -5.9(3) .
