# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_mx172
_database_code_depnum_ccdc_archive 'CCDC 1934798'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             
;
'Tue Apr 11 20:42:09 2017'
;
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
tetrakis(1-aminotetrazolyl) bis(phloroglucinato) copper(II) 
;
_chemical_name_common            
'tetrakis(1-aminotetrazolyl) bis(phloroglucinato) copper(II) '
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Cu N26 O18'
_chemical_formula_sum            'C16 H16 Cu N26 O18'
_chemical_formula_weight         924.09

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_symmetry_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                   10.5340(11)
_cell_length_b                   8.9870(9)
_cell_length_c                   17.0430(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.395(8)
_cell_angle_gamma                90
_cell_volume                     1591.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    791
_cell_measurement_theta_min      4.4450
_cell_measurement_theta_max      21.7740

_exptl_crystal_description       stab
_exptl_crystal_colour            green-yellow
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.813
_shelx_estimated_absorpt_T_min   0.716
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75303
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.928
_exptl_crystal_F_000             934
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            10227
_diffrn_reflns_av_unetI/netI     0.1668
_diffrn_reflns_av_R_equivalents  0.1154
_diffrn_reflns_av_sigmaI/netI    0.2287
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.260
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3104
_reflns_number_gt                1570
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;

_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'enCIFer 1.5.1 (CCDC 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0097P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3104
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      -0.0120524000
_diffrn_orient_matrix_UB_12      0.0006525000
_diffrn_orient_matrix_UB_13      -0.0421698000
_diffrn_orient_matrix_UB_21      0.0671701000
_diffrn_orient_matrix_UB_22      -0.0019463000
_diffrn_orient_matrix_UB_23      -0.0005872000
_diffrn_orient_matrix_UB_31      -0.0017463000
_diffrn_orient_matrix_UB_32      -0.0788930000
_diffrn_orient_matrix_UB_33      -0.0003554000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00   48.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931   77.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3869   77.0000 -180.0000 105

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   89.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3869   77.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3869   77.0000   60.0000 71

#__ type_ start__ end____ width___ exp.time_
  5 omega  -53.00   43.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931   77.0000  -90.0000 96

;



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_
_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 0.5000 0.5000 0.5000 0.0311(3) Uani 1 2 d S . P . .
O1 O 0.6377(4) 0.4143(4) 0.4145(2) 0.0324(11) Uani 1 1 d . . . . .
O2 O 0.6277(4) 0.0183(5) 0.4697(2) 0.0450(13) Uani 1 1 d . . . . .
O3 O 0.7931(5) 0.1632(5) 0.4796(2) 0.0575(15) Uani 1 1 d . . . . .
O4 O 0.6481(4) -0.0701(5) 0.3160(2) 0.0340(11) Uani 1 1 d . . . . .
H4 H 0.6200 -0.1203 0.2753 0.051 Uiso 1 1 calc R U . . .
O5 O 0.5665(4) -0.1071(5) 0.1701(2) 0.0437(13) Uani 1 1 d . . . . .
O6 O 0.5173(4) 0.0784(5) 0.0892(2) 0.0432(13) Uani 1 1 d . . . . .
O7 O 0.5173(4) 0.3441(4) 0.1398(2) 0.0350(11) Uani 1 1 d . . . . .
H7 H 0.5110 0.2767 0.1053 0.053 Uiso 1 1 calc R U . . .
O8 O 0.4568(4) 0.5820(5) 0.2299(2) 0.0392(12) Uani 1 1 d . . . . .
O9 O 0.6504(4) 0.6193(5) 0.2925(2) 0.0410(12) Uani 1 1 d . . . . .
N1 N 0.6669(5) 0.1965(6) 0.6673(3) 0.0312(13) Uani 1 1 d . . . . .
N2 N 0.7583(5) 0.3037(7) 0.6768(3) 0.0395(14) Uani 1 1 d . . . . .
N3 N 0.7152(5) 0.4087(6) 0.6269(3) 0.0348(14) Uani 1 1 d . . . . .
N4 N 0.5983(5) 0.3695(6) 0.5851(3) 0.0289(13) Uani 1 1 d . . . . .
N5 N 0.6753(6) 0.0685(7) 0.7146(4) 0.0453(17) Uani 1 1 d . . . . .
N6 N 0.1877(5) 0.2279(6) 0.4495(3) 0.0367(14) Uani 1 1 d . . . . .
N7 N 0.2528(5) 0.1886(6) 0.3903(3) 0.0394(15) Uani 1 1 d . . . . .
N8 N 0.3621(5) 0.2573(6) 0.4059(3) 0.0444(15) Uani 1 1 d . . . . .
N9 N 0.3664(5) 0.3442(5) 0.4727(3) 0.0287(12) Uani 1 1 d . . . . .
N10 N 0.0650(6) 0.1695(9) 0.4575(3) 0.0448(16) Uani 1 1 d . . . . .
N11 N 0.6927(5) 0.1138(6) 0.4426(3) 0.0339(14) Uani 1 1 d . . . . .
N12 N 0.5526(5) 0.0309(6) 0.1589(3) 0.0357(14) Uani 1 1 d . . . . .
N13 N 0.5624(5) 0.5373(6) 0.2650(3) 0.0285(13) Uani 1 1 d . . . . .
C1 C 0.5717(6) 0.2370(7) 0.6112(3) 0.0310(16) Uani 1 1 d . . . . .
H1 H 0.4968 0.1802 0.5927 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2573(6) 0.3247(7) 0.4978(4) 0.0391(17) Uani 1 1 d . . . . .
H2 H 0.2317 0.3714 0.5428 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6255(5) 0.3282(7) 0.3556(4) 0.0283(15) Uani 1 1 d . . . . .
C4 C 0.6475(5) 0.1735(7) 0.3632(3) 0.0238(14) Uani 1 1 d . . . . .
C5 C 0.6218(5) 0.0729(7) 0.3017(3) 0.0246(14) Uani 1 1 d . . . . .
C6 C 0.5756(5) 0.1281(7) 0.2232(3) 0.0250(14) Uani 1 1 d . . . . .
C7 C 0.5568(5) 0.2848(7) 0.2122(3) 0.0297(15) Uani 1 1 d . . . . .
C8 C 0.5823(6) 0.3772(7) 0.2767(3) 0.0280(15) Uani 1 1 d . . . . .
H10A H -0.001(7) 0.231(8) 0.430(4) 0.07(3) Uiso 1 1 d . . . . .
H5A H 0.710(6) 0.095(7) 0.765(4) 0.06(2) Uiso 1 1 d . . . . .
H5B H 0.723(11) -0.006(13) 0.688(7) 0.23(6) Uiso 1 1 d . . . . .
H10B H 0.032(8) 0.079(10) 0.437(5) 0.13(4) Uiso 1 1 d . . . . .


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 N9 1.986(5) 3_666 ?
Cu1 N9 1.986(5) . ?
Cu1 N4 2.015(5) 3_666 ?
Cu1 N4 2.015(5) . ?
Cu1 O1 2.348(4) . ?
Cu1 O1 2.348(4) 3_666 ?
O1 C3 1.257(6) . ?
O2 N11 1.234(6) . ?
O3 N11 1.223(6) . ?
O4 C5 1.329(6) . ?
O4 H4 0.8400 . ?
O5 N12 1.259(6) . ?
O6 N12 1.260(5) . ?
O7 C7 1.345(6) . ?
O7 H7 0.8400 . ?
O8 N13 1.241(5) . ?
O9 N13 1.216(5) . ?
N1 C1 1.318(6) . ?
N1 N2 1.353(6) . ?
N1 N5 1.399(7) . ?
N2 N3 1.301(6) . ?
N3 N4 1.364(6) . ?
N4 C1 1.317(7) . ?
N5 H5A 0.91(6) . ?
N5 H5B 0.99(11) . ?
N6 C2 1.332(7) . ?
N6 N7 1.355(6) . ?
N6 N10 1.422(7) . ?
N7 N8 1.295(6) . ?
N8 N9 1.376(6) . ?
N9 C2 1.302(7) . ?
N10 H10A 0.94(7) . ?
N10 H10B 0.93(9) . ?
N11 C4 1.462(7) . ?
N12 C6 1.391(7) . ?
N13 C8 1.463(7) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.412(7) . ?
C3 C8 1.419(7) . ?
C4 C5 1.377(7) . ?
C5 C6 1.436(7) . ?
C6 C7 1.430(8) . ?
C7 C8 1.369(7) . ?

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 Cu1 N9 180.00(19) 3_666 . ?
N9 Cu1 N4 91.14(19) 3_666 3_666 ?
N9 Cu1 N4 88.86(19) . 3_666 ?
N9 Cu1 N4 88.86(19) 3_666 . ?
N9 Cu1 N4 91.14(19) . . ?
N4 Cu1 N4 180.0 3_666 . ?
N9 Cu1 O1 83.73(17) 3_666 . ?
N9 Cu1 O1 96.28(17) . . ?
N4 Cu1 O1 92.36(16) 3_666 . ?
N4 Cu1 O1 87.64(16) . . ?
N9 Cu1 O1 96.27(17) 3_666 3_666 ?
N9 Cu1 O1 83.72(17) . 3_666 ?
N4 Cu1 O1 87.64(16) 3_666 3_666 ?
N4 Cu1 O1 92.36(16) . 3_666 ?
O1 Cu1 O1 180.0 . 3_666 ?
C3 O1 Cu1 134.8(4) . . ?
C5 O4 H4 109.5 . . ?
C7 O7 H7 109.5 . . ?
C1 N1 N2 109.4(5) . . ?
C1 N1 N5 127.9(6) . . ?
N2 N1 N5 122.6(5) . . ?
N3 N2 N1 105.8(5) . . ?
N2 N3 N4 110.1(5) . . ?
C1 N4 N3 106.3(5) . . ?
C1 N4 Cu1 131.0(4) . . ?
N3 N4 Cu1 122.7(4) . . ?
N1 N5 H5A 108(4) . . ?
N1 N5 H5B 106(7) . . ?
H5A N5 H5B 117(8) . . ?
C2 N6 N7 109.7(5) . . ?
C2 N6 N10 126.7(6) . . ?
N7 N6 N10 123.6(5) . . ?
N8 N7 N6 105.3(5) . . ?
N7 N8 N9 110.3(5) . . ?
C2 N9 N8 106.5(5) . . ?
C2 N9 Cu1 130.3(4) . . ?
N8 N9 Cu1 121.4(4) . . ?
N6 N10 H10A 110(4) . . ?
N6 N10 H10B 125(5) . . ?
H10A N10 H10B 97(6) . . ?
O3 N11 O2 123.1(5) . . ?
O3 N11 C4 117.9(5) . . ?
O2 N11 C4 119.0(5) . . ?
O5 N12 O6 119.1(5) . . ?
O5 N12 C6 119.8(5) . . ?
O6 N12 C6 121.1(6) . . ?
O9 N13 O8 123.8(5) . . ?
O9 N13 C8 117.4(5) . . ?
O8 N13 C8 118.7(5) . . ?
N4 C1 N1 108.4(5) . . ?
N4 C1 H1 125.8 . . ?
N1 C1 H1 125.8 . . ?
N9 C2 N6 108.1(6) . . ?
N9 C2 H2 126.0 . . ?
N6 C2 H2 126.0 . . ?
O1 C3 C4 122.6(5) . . ?
O1 C3 C8 122.8(6) . . ?
C4 C3 C8 114.5(5) . . ?
C5 C4 C3 124.6(5) . . ?
C5 C4 N11 117.3(5) . . ?
C3 C4 N11 118.0(5) . . ?
O4 C5 C4 119.1(5) . . ?
O4 C5 C6 122.3(5) . . ?
C4 C5 C6 118.5(5) . . ?
N12 C6 C7 120.8(5) . . ?
N12 C6 C5 120.4(6) . . ?
C7 C6 C5 118.7(5) . . ?
O7 C7 C8 119.1(6) . . ?
O7 C7 C6 121.8(5) . . ?
C8 C7 C6 119.1(5) . . ?
C7 C8 C3 124.3(6) . . ?
C7 C8 N13 118.9(5) . . ?
C3 C8 N13 116.8(5) . . ?

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 N1 N2 N3 1.2(7) . . . . ?
N5 N1 N2 N3 -175.9(5) . . . . ?
N1 N2 N3 N4 -0.7(6) . . . . ?
N2 N3 N4 C1 0.0(6) . . . . ?
N2 N3 N4 Cu1 -178.7(4) . . . . ?
C2 N6 N7 N8 2.6(7) . . . . ?
N10 N6 N7 N8 -176.2(6) . . . . ?
N6 N7 N8 N9 -2.1(7) . . . . ?
N7 N8 N9 C2 0.8(7) . . . . ?
N7 N8 N9 Cu1 -165.6(4) . . . . ?
N3 N4 C1 N1 0.7(6) . . . . ?
Cu1 N4 C1 N1 179.3(4) . . . . ?
N2 N1 C1 N4 -1.2(7) . . . . ?
N5 N1 C1 N4 175.7(6) . . . . ?
N8 N9 C2 N6 0.8(7) . . . . ?
Cu1 N9 C2 N6 165.6(4) . . . . ?
N7 N6 C2 N9 -2.1(7) . . . . ?
N10 N6 C2 N9 176.6(6) . . . . ?
Cu1 O1 C3 C4 -89.6(7) . . . . ?
Cu1 O1 C3 C8 87.2(7) . . . . ?
O1 C3 C4 C5 172.5(5) . . . . ?
C8 C3 C4 C5 -4.5(9) . . . . ?
O1 C3 C4 N11 -3.2(9) . . . . ?
C8 C3 C4 N11 179.8(5) . . . . ?
O3 N11 C4 C5 126.1(6) . . . . ?
O2 N11 C4 C5 -55.0(7) . . . . ?
O3 N11 C4 C3 -57.9(8) . . . . ?
O2 N11 C4 C3 121.1(6) . . . . ?
C3 C4 C5 O4 179.2(5) . . . . ?
N11 C4 C5 O4 -5.1(8) . . . . ?
C3 C4 C5 C6 3.4(9) . . . . ?
N11 C4 C5 C6 179.2(5) . . . . ?
O5 N12 C6 C7 -178.1(5) . . . . ?
O6 N12 C6 C7 1.5(8) . . . . ?
O5 N12 C6 C5 3.4(8) . . . . ?
O6 N12 C6 C5 -177.0(5) . . . . ?
O4 C5 C6 N12 2.2(8) . . . . ?
C4 C5 C6 N12 177.8(5) . . . . ?
O4 C5 C6 C7 -176.3(5) . . . . ?
C4 C5 C6 C7 -0.7(8) . . . . ?
N12 C6 C7 O7 -0.4(8) . . . . ?
C5 C6 C7 O7 178.0(5) . . . . ?
N12 C6 C7 C8 -179.0(5) . . . . ?
C5 C6 C7 C8 -0.5(8) . . . . ?
O7 C7 C8 C3 -179.4(5) . . . . ?
C6 C7 C8 C3 -0.8(9) . . . . ?
O7 C7 C8 N13 1.6(8) . . . . ?
C6 C7 C8 N13 -179.8(5) . . . . ?
O1 C3 C8 C7 -173.9(5) . . . . ?
C4 C3 C8 C7 3.1(9) . . . . ?
O1 C3 C8 N13 5.2(9) . . . . ?
C4 C3 C8 N13 -177.9(5) . . . . ?
O9 N13 C8 C7 -129.3(6) . . . . ?
O8 N13 C8 C7 52.6(8) . . . . ?
O9 N13 C8 C3 51.7(7) . . . . ?
O8 N13 C8 C3 -126.4(6) . . . . ?

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
O4 H4 O5 0.84 1.79 2.517(5) 143.2 .
O4 H4 O9 0.84 2.37 2.821(6) 114.0 1_545
O4 H4 N12 0.84 2.41 2.851(6) 113.1 .
O7 H7 O6 0.84 1.81 2.540(6) 144.9 .
O7 H7 N12 0.84 2.40 2.851(7) 114.1 .
N10 H10A O5 0.94(7) 2.27(7) 3.114(8) 149(6) 2
N5 H5A N3 0.91(6) 2.51(6) 3.109(8) 123(5) 2_646
N5 H5B N7 0.99(11) 2.16(12) 3.091(9) 156(10) 3_656
N5 H5B O8 0.99(11) 2.54(11) 3.231(8) 127(8) 4_666
N10 H10B O7 0.93(9) 2.50(9) 3.404(8) 166(7) 2_545

_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.
;



_refine_diff_density_max         0.868
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.106

_shelxl_version_number           2013-4


####################################################################### 
# 
# 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_nx263
_database_code_depnum_ccdc_archive 'CCDC 1934805'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2018-07-11
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
bis(1-amino-5-methyltetrazolyl) copper(II) styphnate
;
_chemical_name_common            
'bis(1-amino-5-methyltetrazolyl) copper(II) styphnate'
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 Cu N13 O8'
_chemical_formula_sum            'C10 H11 Cu N13 O8'
_chemical_formula_weight         504.86

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'


_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+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.6007(14)
_cell_length_b                   15.0584(14)
_cell_length_c                   8.0850(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1777.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1307
_cell_measurement_theta_min      4.6170
_cell_measurement_theta_max      24.9710

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.537
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    1.309
_shelx_estimated_absorpt_T_min   0.540
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92714
_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.
;

_exptl_special_details           ?


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_F_000             1020
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_probe          x-ray
_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            13583
_diffrn_reflns_av_unetI/netI     0.1287
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_av_sigmaI/netI    0.1610
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.293
_diffrn_reflns_theta_max         29.441
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4360
_reflns_number_gt                2894
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_max     0.833
_reflns_Friedel_fraction_full    0.984

_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    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Encifer 1.5.1, CCDC 2014'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0102P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_refine_ls_abs_structure_Flack   -0.025(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4360
_refine_ls_number_parameters     299
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000



_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
;



_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      -0.0434705000
_diffrn_orient_matrix_UB_12      0.0203713000
_diffrn_orient_matrix_UB_13      -0.0097226000
_diffrn_orient_matrix_UB_21      0.0201345000
_diffrn_orient_matrix_UB_22      0.0422373000
_diffrn_orient_matrix_UB_23      0.0138618000
_diffrn_orient_matrix_UB_31      0.0081048000
_diffrn_orient_matrix_UB_32      0.0044687000
_diffrn_orient_matrix_UB_33      -0.0860613000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  17.00   1.00   42.00    --  -21.75 -99.00 120.00   42
  2  ω    -99.00 -34.00   1.00   42.00    --  -21.75-179.00 -90.00   65
  3  ω    -41.00  18.00   1.00   42.00    --  -21.75  38.00 120.00   59
  4  ω    -25.00  23.00   1.00   42.00    --  -21.75 -99.00 -90.00   48
  5  ω     -7.00  80.00   1.00   42.00    --   22.84  38.00 -90.00   87
  6  ω     39.00  92.00   1.00   42.00    --   22.84  57.00 -60.00   53
  7  ω    -48.00   7.00   1.00   42.00    --   22.84 -57.00 150.00   55
;



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_
_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 0.57004(6) 0.78803(5) 0.82639(11) 0.01608(18) Uani 1 1 d . . . . .
O1 O 0.5697(3) 0.8249(3) 0.5942(6) 0.0173(11) Uani 1 1 d . . . . .
O2 O 0.4408(4) 0.8561(3) 0.3261(9) 0.0363(13) Uani 1 1 d . . . . .
O3 O 0.3659(4) 0.9249(4) 0.5152(8) 0.0458(18) Uani 1 1 d . . . . .
O4 O 0.4513(3) 1.0896(3) 0.3882(5) 0.0182(12) Uani 1 1 d . . . . .
O5 O 0.5811(3) 1.2252(3) 0.3562(7) 0.0297(16) Uani 1 1 d . . . . .
O6 O 0.6889(4) 1.2179(4) 0.5348(6) 0.0361(15) Uani 1 1 d . . . . .
O7 O 0.8042(4) 0.9624(4) 0.7410(6) 0.0323(14) Uani 1 1 d . . . . .
O8 O 0.7294(4) 0.8391(3) 0.7564(5) 0.0224(12) Uani 1 1 d . . . . .
N2 N 0.5693(4) 0.5436(4) 0.6047(7) 0.0178(13) Uani 1 1 d . . . . .
N3 N 0.6430(4) 0.5350(4) 0.7045(7) 0.0237(15) Uani 1 1 d . . . . .
N4 N 0.6487(4) 0.6075(4) 0.7863(7) 0.0234(16) Uani 1 1 d . . . . .
N5 N 0.5798(4) 0.6643(4) 0.7402(7) 0.0190(14) Uani 1 1 d . . . . .
N6 N 0.5412(4) 0.4799(4) 0.4893(6) 0.0229(16) Uani 1 1 d . . . . .
H6A H 0.589874 0.474486 0.454595 0.028 Uiso 1 1 d R U . . .
H6B H 0.517667 0.436208 0.555844 0.028 Uiso 1 1 d R U . . .
N7 N 0.6689(4) 0.7360(4) 1.2904(6) 0.0168(15) Uani 1 1 d . . . . .
N8 N 0.6177(4) 0.6620(4) 1.2653(7) 0.0216(15) Uani 1 1 d . . . . .
N9 N 0.5774(4) 0.6747(4) 1.1253(7) 0.0213(15) Uani 1 1 d . . . . .
N10 N 0.6008(4) 0.7550(4) 1.0608(7) 0.0189(14) Uani 1 1 d . . . . .
N11 N 0.7294(5) 0.7454(5) 1.4238(8) 0.0243(17) Uani 1 1 d . . . . .
N12 N 0.4363(5) 0.9101(4) 0.4377(8) 0.0254(15) Uani 1 1 d . . . . .
N13 N 0.6274(5) 1.1829(4) 0.4584(7) 0.0223(15) Uani 1 1 d . . . . .
N14 N 0.7375(4) 0.9165(4) 0.7051(7) 0.0211(15) Uani 1 1 d . . . . .
C1 C 0.5302(5) 0.6234(5) 0.6250(8) 0.0159(16) Uani 1 1 d . . . . .
C2 C 0.4489(5) 0.6551(5) 0.5371(9) 0.0237(19) Uani 1 1 d . . . . .
H2A H 0.465996 0.704365 0.464091 0.035 Uiso 1 1 calc R U . . .
H2B H 0.403239 0.675547 0.617240 0.035 Uiso 1 1 calc R U . . .
H2C H 0.423174 0.606606 0.470966 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6590(5) 0.7934(5) 1.1672(8) 0.0182(16) Uani 1 1 d . . . . .
C4 C 0.7043(5) 0.8795(4) 1.1563(9) 0.0241(19) Uani 1 1 d . . . . .
H4A H 0.751723 0.883530 1.241811 0.036 Uiso 1 1 calc R U . . .
H4B H 0.659161 0.926789 1.172919 0.036 Uiso 1 1 calc R U . . .
H4C H 0.732498 0.885962 1.046993 0.036 Uiso 1 1 calc R U . . .
C5 C 0.5861(5) 0.9080(5) 0.5603(8) 0.0149(16) Uani 1 1 d . . . . .
C6 C 0.5201(5) 0.9589(4) 0.4793(8) 0.0168(17) Uani 1 1 d . . . . .
C7 C 0.5227(5) 1.0501(4) 0.4436(8) 0.0144(16) Uani 1 1 d . . . . .
C8 C 0.6098(5) 1.0897(5) 0.4840(8) 0.0164(16) Uani 1 1 d . . . . .
C9 C 0.6772(5) 1.0426(5) 0.5629(8) 0.0189(17) Uani 1 1 d . . . . .
H9 H 0.732887 1.071739 0.590042 0.023 Uiso 1 1 calc R U . . .
C10 C 0.6670(5) 0.9543(5) 0.6045(8) 0.0162(16) Uani 1 1 d . . . . .
H11A H 0.693(5) 0.751(5) 1.521(8) 0.02(2) Uiso 1 1 d . . . . .
H11B H 0.761(6) 0.705(5) 1.415(10) 0.04(3) Uiso 1 1 d . . . . .


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 O4 1.934(4) 2_675 ?
Cu1 O1 1.958(5) . ?
Cu1 N5 1.994(6) . ?
Cu1 N10 2.011(6) . ?
Cu1 O5 2.229(5) 2_675 ?
O1 C5 1.303(8) . ?
O2 N12 1.217(8) . ?
O3 N12 1.225(8) . ?
O4 C7 1.281(8) . ?
O5 N13 1.243(7) . ?
O6 N13 1.211(7) . ?
O7 N14 1.230(7) . ?
O8 N14 1.243(7) . ?
N2 C1 1.340(8) . ?
N2 N3 1.351(8) . ?
N2 N6 1.400(7) . ?
N3 N4 1.279(8) . ?
N4 N5 1.372(8) . ?
N5 C1 1.331(9) . ?
N6 H6A 0.7692 . ?
N6 H6B 0.9162 . ?
N7 C3 1.327(8) . ?
N7 N8 1.357(7) . ?
N7 N11 1.401(8) . ?
N8 N9 1.290(7) . ?
N9 N10 1.361(8) . ?
N10 C3 1.340(8) . ?
N11 H11A 0.95(7) . ?
N11 H11B 0.77(8) . ?
N12 C6 1.465(9) . ?
N13 C8 1.442(9) . ?
N14 C10 1.430(8) . ?
C1 C2 1.463(9) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.458(9) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.394(9) . ?
C5 C10 1.417(9) . ?
C6 C7 1.404(9) . ?
C7 C8 1.443(10) . ?
C8 C9 1.371(10) . ?
C9 C10 1.379(9) . ?
C9 H9 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
O4 Cu1 O1 88.72(18) 2_675 . ?
O4 Cu1 N5 172.6(2) 2_675 . ?
O1 Cu1 N5 86.0(2) . . ?
O4 Cu1 N10 91.6(2) 2_675 . ?
O1 Cu1 N10 167.1(2) . . ?
N5 Cu1 N10 94.7(2) . . ?
O4 Cu1 O5 84.10(18) 2_675 2_675 ?
O1 Cu1 O5 97.2(2) . 2_675 ?
N5 Cu1 O5 91.4(2) . 2_675 ?
N10 Cu1 O5 95.6(2) . 2_675 ?
C5 O1 Cu1 118.2(4) . . ?
C7 O4 Cu1 131.6(4) . 2_674 ?
N13 O5 Cu1 124.4(5) . 2_674 ?
C1 N2 N3 110.6(6) . . ?
C1 N2 N6 124.9(6) . . ?
N3 N2 N6 124.4(6) . . ?
N4 N3 N2 106.2(6) . . ?
N3 N4 N5 110.1(6) . . ?
C1 N5 N4 107.5(6) . . ?
C1 N5 Cu1 129.7(5) . . ?
N4 N5 Cu1 122.7(5) . . ?
N2 N6 H6A 92.5 . . ?
N2 N6 H6B 102.2 . . ?
H6A N6 H6B 119.0 . . ?
C3 N7 N8 111.2(6) . . ?
C3 N7 N11 125.5(6) . . ?
N8 N7 N11 123.0(6) . . ?
N9 N8 N7 105.1(5) . . ?
N8 N9 N10 110.7(6) . . ?
C3 N10 N9 107.3(6) . . ?
C3 N10 Cu1 129.8(5) . . ?
N9 N10 Cu1 121.7(5) . . ?
N7 N11 H11A 107(4) . . ?
N7 N11 H11B 103(6) . . ?
H11A N11 H11B 119(7) . . ?
O2 N12 O3 123.1(7) . . ?
O2 N12 C6 117.4(7) . . ?
O3 N12 C6 119.5(6) . . ?
O6 N13 O5 121.3(6) . . ?
O6 N13 C8 118.9(6) . . ?
O5 N13 C8 119.8(6) . . ?
O7 N14 O8 121.6(6) . . ?
O7 N14 C10 118.8(6) . . ?
O8 N14 C10 119.7(6) . . ?
N5 C1 N2 105.6(6) . . ?
N5 C1 C2 129.1(7) . . ?
N2 C1 C2 125.3(6) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N7 C3 N10 105.7(6) . . ?
N7 C3 C4 125.1(7) . . ?
N10 C3 C4 129.2(7) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 C6 119.9(7) . . ?
O1 C5 C10 125.0(6) . . ?
C6 C5 C10 115.1(6) . . ?
C5 C6 C7 128.0(7) . . ?
C5 C6 N12 114.2(6) . . ?
C7 C6 N12 117.7(6) . . ?
O4 C7 C6 120.4(7) . . ?
O4 C7 C8 127.1(6) . . ?
C6 C7 C8 112.4(7) . . ?
C9 C8 N13 116.3(7) . . ?
C9 C8 C7 121.6(6) . . ?
N13 C8 C7 121.8(7) . . ?
C8 C9 C10 122.3(7) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C9 C10 C5 120.2(7) . . ?
C9 C10 N14 116.4(6) . . ?
C5 C10 N14 123.2(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
C1 N2 N3 N4 0.8(8) . . . . ?
N6 N2 N3 N4 177.3(6) . . . . ?
N2 N3 N4 N5 -0.5(8) . . . . ?
N3 N4 N5 C1 0.1(8) . . . . ?
N3 N4 N5 Cu1 -175.3(5) . . . . ?
C3 N7 N8 N9 0.5(7) . . . . ?
N11 N7 N8 N9 -174.7(6) . . . . ?
N7 N8 N9 N10 -0.4(7) . . . . ?
N8 N9 N10 C3 0.2(8) . . . . ?
N8 N9 N10 Cu1 168.5(5) . . . . ?
Cu1 O5 N13 O6 -139.4(6) 2_674 . . . ?
Cu1 O5 N13 C8 42.5(9) 2_674 . . . ?
N4 N5 C1 N2 0.3(8) . . . . ?
Cu1 N5 C1 N2 175.3(5) . . . . ?
N4 N5 C1 C2 179.5(7) . . . . ?
Cu1 N5 C1 C2 -5.6(12) . . . . ?
N3 N2 C1 N5 -0.7(8) . . . . ?
N6 N2 C1 N5 -177.2(6) . . . . ?
N3 N2 C1 C2 -179.8(6) . . . . ?
N6 N2 C1 C2 3.6(11) . . . . ?
N8 N7 C3 N10 -0.3(8) . . . . ?
N11 N7 C3 N10 174.7(6) . . . . ?
N8 N7 C3 C4 179.8(7) . . . . ?
N11 N7 C3 C4 -5.1(11) . . . . ?
N9 N10 C3 N7 0.1(7) . . . . ?
Cu1 N10 C3 N7 -166.9(5) . . . . ?
N9 N10 C3 C4 179.9(7) . . . . ?
Cu1 N10 C3 C4 12.9(11) . . . . ?
Cu1 O1 C5 C6 -119.2(6) . . . . ?
Cu1 O1 C5 C10 58.6(8) . . . . ?
O1 C5 C6 C7 174.9(6) . . . . ?
C10 C5 C6 C7 -3.1(11) . . . . ?
O1 C5 C6 N12 -0.8(9) . . . . ?
C10 C5 C6 N12 -178.8(6) . . . . ?
O2 N12 C6 C5 -72.4(8) . . . . ?
O3 N12 C6 C5 107.5(8) . . . . ?
O2 N12 C6 C7 111.3(7) . . . . ?
O3 N12 C6 C7 -68.8(9) . . . . ?
Cu1 O4 C7 C6 -179.9(4) 2_674 . . . ?
Cu1 O4 C7 C8 3.3(10) 2_674 . . . ?
C5 C6 C7 O4 -170.5(7) . . . . ?
N12 C6 C7 O4 5.1(10) . . . . ?
C5 C6 C7 C8 6.7(10) . . . . ?
N12 C6 C7 C8 -177.7(6) . . . . ?
O6 N13 C8 C9 -15.0(10) . . . . ?
O5 N13 C8 C9 163.2(7) . . . . ?
O6 N13 C8 C7 159.1(7) . . . . ?
O5 N13 C8 C7 -22.7(10) . . . . ?
O4 C7 C8 C9 171.2(7) . . . . ?
C6 C7 C8 C9 -5.8(10) . . . . ?
O4 C7 C8 N13 -2.6(11) . . . . ?
C6 C7 C8 N13 -179.6(6) . . . . ?
N13 C8 C9 C10 175.9(6) . . . . ?
C7 C8 C9 C10 1.8(11) . . . . ?
C8 C9 C10 C5 2.4(10) . . . . ?
C8 C9 C10 N14 -172.2(6) . . . . ?
O1 C5 C10 C9 -179.7(6) . . . . ?
C6 C5 C10 C9 -1.8(9) . . . . ?
O1 C5 C10 N14 -5.6(11) . . . . ?
C6 C5 C10 N14 172.3(6) . . . . ?
O7 N14 C10 C9 -3.7(9) . . . . ?
O8 N14 C10 C9 175.1(6) . . . . ?
O7 N14 C10 C5 -178.0(6) . . . . ?
O8 N14 C10 C5 0.7(10) . . . . ?

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
C2 H2A O1 0.98 2.59 3.139(9) 115.8 .




_refine_diff_density_max         0.638
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.117

_shelxl_version_number           ?


####################################################################### 
# 
# 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_nx281
_database_code_depnum_ccdc_archive 'CCDC 1934807'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2018-07-24
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
monoaqua tetrakis(1-amino-5-methyl-tetrazolyl)copper(II) trinitrophloglucinate
;
_chemical_name_common            
;
monoaqua tetrakis(1-amino-5-methyl-tetrazolyl)copper(II) trinitrophloglucinate
;
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H22 Cu N20 O, 2(C6 H2 N3 O9)'
_chemical_formula_sum            'C20 H26 Cu N26 O19'
_chemical_formula_weight         998.21

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_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                   6.8633(3)
_cell_length_b                   16.3608(8)
_cell_length_c                   32.863(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.152(5)
_cell_angle_gamma                90
_cell_volume                     3687.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    2439
_cell_measurement_theta_min      4.3300
_cell_measurement_theta_max      25.2180

_exptl_crystal_description       rod
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.081
_exptl_absorpt_coefficient_mu    0.711
_shelx_estimated_absorpt_T_min   0.807
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99225
_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.
;

_exptl_special_details           
;
 ?
;


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_F_000             2036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_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            20880
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_sigmaI/netI    0.1182
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         4.175
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7501
_reflns_number_gt                4672
_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    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'enCIFer 1.5.1 (CCDC 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7501
_refine_ls_number_parameters     655
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      -0.0013936000
_diffrn_orient_matrix_UB_12      0.0260275000
_diffrn_orient_matrix_UB_13      -0.0172555000
_diffrn_orient_matrix_UB_21      0.0355988000
_diffrn_orient_matrix_UB_22      -0.0324674000
_diffrn_orient_matrix_UB_23      -0.0119700000
_diffrn_orient_matrix_UB_31      -0.0970956000
_diffrn_orient_matrix_UB_32      -0.0122489000
_diffrn_orient_matrix_UB_33      -0.0049888000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00   3.00   1.00   37.50    --  -20.29 -57.00  30.00   93
  2  ω    -44.00  50.00   1.00   37.50    --  -20.29  57.00-180.00   94
  3  ω    -13.00  25.00   1.00   37.50    --  -20.29 -99.00-180.00   38
  4  ω    -49.00  52.00   1.00   37.50    --   21.39 -77.00 -60.00  101
;



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_
_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 0.32790(5) 0.24879(3) 0.37586(2) 0.01631(13) Uani 1 1 d . . . . .
O1 O 0.6524(4) 0.2570(2) 0.37725(11) 0.0275(7) Uani 1 1 d . . . . .
N1 N 0.2375(4) 0.07649(18) 0.28585(9) 0.0177(7) Uani 1 1 d . . . . .
N2 N 0.0542(4) 0.09617(19) 0.29610(10) 0.0237(7) Uani 1 1 d . . . . .
N3 N 0.0726(4) 0.14855(19) 0.32537(10) 0.0250(8) Uani 1 1 d . . . . .
N4 N 0.2666(4) 0.16260(17) 0.33417(9) 0.0170(7) Uani 1 1 d . . . . .
N5 N 0.2599(5) 0.0227(2) 0.25348(11) 0.0247(8) Uani 1 1 d . . . . .
N6 N 0.2767(4) 0.43201(18) 0.29018(9) 0.0196(7) Uani 1 1 d . . . . .
N7 N 0.4632(4) 0.4415(2) 0.30475(10) 0.0268(8) Uani 1 1 d . . . . .
N8 N 0.4925(4) 0.38394(18) 0.33112(10) 0.0249(8) Uani 1 1 d . . . . .
N9 N 0.3256(4) 0.33810(17) 0.33406(9) 0.0176(7) Uani 1 1 d . . . . .
N10 N 0.2062(6) 0.4870(2) 0.26094(12) 0.0263(9) Uani 1 1 d . . . . .
N11 N 0.1923(4) 0.41710(18) 0.46323(9) 0.0189(7) Uani 1 1 d . . . . .
N12 N 0.0118(4) 0.39356(19) 0.44919(10) 0.0257(8) Uani 1 1 d . . . . .
N13 N 0.0377(4) 0.34042(19) 0.42103(10) 0.0235(8) Uani 1 1 d . . . . .
N14 N 0.2351(4) 0.32966(18) 0.41634(9) 0.0178(7) Uani 1 1 d . . . . .
N15 N 0.2310(4) 0.4742(2) 0.49367(11) 0.0214(8) Uani 1 1 d . . . . .
N16 N 0.3162(4) 0.08676(18) 0.47081(10) 0.0232(7) Uani 1 1 d . . . . .
N17 N 0.5046(4) 0.11169(19) 0.47300(10) 0.0251(8) Uani 1 1 d . . . . .
N18 N 0.5251(4) 0.15951(19) 0.44256(9) 0.0226(7) Uani 1 1 d . . . . .
N19 N 0.3517(4) 0.16624(18) 0.42055(9) 0.0199(7) Uani 1 1 d . . . . .
N20 N 0.2310(6) 0.0377(3) 0.49988(13) 0.0344(10) Uani 1 1 d . . . . .
C1 C 0.3679(5) 0.1170(2) 0.30959(11) 0.0166(8) Uani 1 1 d . . . . .
C2 C 0.5824(5) 0.1111(2) 0.30748(12) 0.0275(10) Uani 1 1 d . . . . .
H2A H 0.6427 0.1602 0.3195 0.041 Uiso 1 1 calc R U . . .
H2B H 0.6179 0.1064 0.2790 0.041 Uiso 1 1 calc R U . . .
H2C H 0.6287 0.0628 0.3226 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1922(5) 0.3695(2) 0.30863(11) 0.0182(8) Uani 1 1 d . . . . .
C4 C -0.0127(5) 0.3443(2) 0.30207(12) 0.0281(10) Uani 1 1 d . . . . .
H4A H -0.0329 0.2913 0.3151 0.042 Uiso 1 1 calc R U . . .
H4B H -0.0433 0.3397 0.2728 0.042 Uiso 1 1 calc R U . . .
H4C H -0.0981 0.3852 0.3139 0.042 Uiso 1 1 calc R U . . .
C5 C 0.3274(5) 0.3779(2) 0.44277(11) 0.0179(8) Uani 1 1 d . . . . .
C6 C 0.5400(5) 0.3893(2) 0.44962(12) 0.0313(10) Uani 1 1 d . . . . .
H6A H 0.6010 0.3365 0.4561 0.047 Uiso 1 1 calc R U . . .
H6B H 0.5642 0.4271 0.4724 0.047 Uiso 1 1 calc R U . . .
H6C H 0.5955 0.4117 0.4250 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2235(5) 0.1205(2) 0.43888(11) 0.0196(8) Uani 1 1 d . . . . .
C8 C 0.0139(5) 0.1086(2) 0.42780(12) 0.0280(10) Uani 1 1 d . . . . .
H8A H -0.0094 0.1207 0.3988 0.042 Uiso 1 1 calc R U . . .
H8B H -0.0646 0.1455 0.4441 0.042 Uiso 1 1 calc R U . . .
H8C H -0.0229 0.0519 0.4332 0.042 Uiso 1 1 calc R U . . .
O2 O 0.8271(4) 0.25583(19) 0.00525(9) 0.0424(8) Uani 1 1 d . . . . .
O3 O 1.1392(4) 0.2664(2) 0.00861(9) 0.0448(9) Uani 1 1 d . . . . .
O4 O 0.9666(3) 0.09798(16) 0.05369(8) 0.0282(6) Uani 1 1 d . . . . .
O5 O 0.8083(4) 0.01724(18) 0.12316(9) 0.0425(8) Uani 1 1 d . . . . .
O6 O 1.0700(4) 0.03140(18) 0.16089(9) 0.0440(8) Uani 1 1 d . . . . .
O7 O 0.9648(4) 0.1840(2) 0.19001(10) 0.0378(8) Uani 1 1 d . . . . .
O8 O 1.0151(4) 0.33645(19) 0.20260(9) 0.0426(8) Uani 1 1 d . . . . .
O9 O 1.0584(4) 0.42148(17) 0.15308(9) 0.0404(8) Uani 1 1 d . . . . .
O10 O 1.0156(4) 0.37841(18) 0.07932(10) 0.0354(8) Uani 1 1 d . . . . .
N21 N 0.9841(5) 0.25539(19) 0.02412(10) 0.0264(7) Uani 1 1 d . . . . .
N22 N 0.9455(4) 0.0580(2) 0.13659(10) 0.0289(8) Uani 1 1 d . . . . .
N23 N 1.0246(4) 0.3503(2) 0.16521(11) 0.0317(9) Uani 1 1 d . . . . .
C10 C 0.9824(5) 0.2388(2) 0.06801(11) 0.0198(8) Uani 1 1 d . . . . .
C11 C 0.9682(5) 0.1543(2) 0.07936(12) 0.0236(9) Uani 1 1 d . . . . .
C12 C 0.9631(5) 0.1419(2) 0.12238(12) 0.0214(9) Uani 1 1 d . . . . .
C13 C 0.9753(5) 0.2038(3) 0.15058(12) 0.0242(9) Uani 1 1 d . . . . .
C14 C 0.9979(5) 0.2863(2) 0.13720(12) 0.0249(9) Uani 1 1 d . . . . .
C15 C 1.0004(5) 0.3026(2) 0.09451(12) 0.0229(9) Uani 1 1 d . . . . .
O11 O 0.5026(4) 0.41506(15) 0.19609(8) 0.0299(7) Uani 1 1 d . . . . .
O12 O 0.6762(4) 0.48481(18) 0.12342(9) 0.0432(8) Uani 1 1 d . . . . .
O13 O 0.4002(4) 0.47606(17) 0.09036(10) 0.0451(8) Uani 1 1 d . . . . .
O14 O 0.4989(4) 0.3183(2) 0.06184(10) 0.0320(8) Uani 1 1 d . . . . .
O15 O 0.4700(4) 0.16459(18) 0.05217(9) 0.0409(8) Uani 1 1 d . . . . .
O16 O 0.4142(4) 0.08331(17) 0.10262(9) 0.0377(7) Uani 1 1 d . . . . .
O17 O 0.4525(4) 0.13175(18) 0.17613(10) 0.0325(8) Uani 1 1 d . . . . .
O18 O 0.3316(4) 0.23013(18) 0.24285(9) 0.0415(8) Uani 1 1 d . . . . .
O19 O 0.6201(4) 0.2805(2) 0.24965(9) 0.0556(10) Uani 1 1 d . . . . .
N24 N 0.5286(5) 0.4470(2) 0.11292(10) 0.0284(8) Uani 1 1 d . . . . .
N25 N 0.4520(4) 0.1529(2) 0.08938(11) 0.0297(8) Uani 1 1 d . . . . .
N26 N 0.4793(5) 0.2593(2) 0.22897(10) 0.0283(8) Uani 1 1 d . . . . .
C16 C 0.5009(5) 0.3561(2) 0.17221(12) 0.0214(9) Uani 1 1 d . . . . .
C17 C 0.5069(5) 0.3644(2) 0.12881(12) 0.0209(9) Uani 1 1 d . . . . .
C18 C 0.4920(5) 0.3013(2) 0.10153(11) 0.0216(9) Uani 1 1 d . . . . .
C19 C 0.4708(5) 0.2195(2) 0.11655(12) 0.0202(9) Uani 1 1 d . . . . .
C20 C 0.4663(5) 0.2064(2) 0.15971(12) 0.0219(9) Uani 1 1 d . . . . .
C21 C 0.4849(5) 0.2725(2) 0.18505(12) 0.0215(9) Uani 1 1 d . . . . .
H1A H 0.689(7) 0.243(3) 0.3990(16) 0.07(2) Uiso 1 1 d . . . . .
H1B H 0.679(8) 0.303(4) 0.3703(18) 0.10(3) Uiso 1 1 d . . . . .
H10A H 0.107(6) 0.507(3) 0.2682(14) 0.053(17) Uiso 1 1 d . . . . .
H10B H 0.191(6) 0.464(3) 0.2404(14) 0.040(15) Uiso 1 1 d . . . . .
H15A H 0.170(5) 0.459(2) 0.5137(11) 0.021(11) Uiso 1 1 d . . . . .
H15B H 0.183(5) 0.523(3) 0.4840(13) 0.045(14) Uiso 1 1 d . . . . .
H20B H 0.229(6) 0.062(3) 0.5228(14) 0.051(17) Uiso 1 1 d . . . . .
H20A H 0.295(6) -0.002(3) 0.5022(14) 0.045(16) Uiso 1 1 d . . . . .
H5A H 0.319(5) 0.054(3) 0.2329(13) 0.050(14) Uiso 1 1 d . . . . .
H5B H 0.339(6) -0.015(3) 0.2627(13) 0.051(15) Uiso 1 1 d . . . . .
H7 H 0.979(6) 0.223(2) 0.2007(14) 0.032(15) Uiso 1 1 d . . . . .
H10 H 1.041(6) 0.405(3) 0.0995(13) 0.038(14) Uiso 1 1 d . . . . .
H17 H 0.450(5) 0.102(2) 0.1574(12) 0.031(14) Uiso 1 1 d . . . . .
H14 H 0.506(8) 0.280(3) 0.0545(18) 0.08(2) Uiso 1 1 d . . . . .


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 N19 1.997(3) . ?
Cu1 N14 1.998(3) . ?
Cu1 N4 2.000(3) . ?
Cu1 N9 2.005(3) . ?
Cu1 O1 2.230(3) . ?
O1 H1A 0.79(5) . ?
O1 H1B 0.81(6) . ?
N1 C1 1.341(4) . ?
N1 N2 1.353(4) . ?
N1 N5 1.394(4) . ?
N2 N3 1.291(4) . ?
N3 N4 1.371(4) . ?
N4 C1 1.317(4) . ?
N5 H5A 0.95(4) . ?
N5 H5B 0.87(4) . ?
N6 C3 1.333(4) . ?
N6 N7 1.359(4) . ?
N6 N10 1.390(4) . ?
N7 N8 1.291(4) . ?
N8 N9 1.375(4) . ?
N9 C3 1.321(4) . ?
N10 H10A 0.80(4) . ?
N10 H10B 0.77(4) . ?
N11 C5 1.330(4) . ?
N11 N12 1.361(4) . ?
N11 N15 1.387(4) . ?
N12 N13 1.287(4) . ?
N13 N14 1.380(3) . ?
N14 C5 1.318(4) . ?
N15 H15A 0.83(3) . ?
N15 H15B 0.91(4) . ?
N16 C7 1.327(4) . ?
N16 N17 1.356(4) . ?
N16 N20 1.393(4) . ?
N17 N18 1.282(4) . ?
N18 N19 1.374(4) . ?
N19 C7 1.318(4) . ?
N20 H20B 0.85(5) . ?
N20 H20A 0.78(4) . ?
C1 C2 1.479(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.473(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.480(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.484(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O2 N21 1.223(4) . ?
O3 N21 1.211(4) . ?
O4 C11 1.250(4) . ?
O5 N22 1.222(4) . ?
O6 N22 1.227(4) . ?
O7 C13 1.340(5) . ?
O7 H7 0.74(4) . ?
O8 N23 1.253(4) . ?
O9 N23 1.256(4) . ?
O10 C15 1.342(4) . ?
O10 H10 0.81(4) . ?
N21 C10 1.468(5) . ?
N22 C12 1.456(5) . ?
N23 C14 1.402(5) . ?
C10 C15 1.363(5) . ?
C10 C11 1.435(5) . ?
C11 C12 1.430(5) . ?
C12 C13 1.373(5) . ?
C13 C14 1.429(5) . ?
C14 C15 1.429(5) . ?
O11 C16 1.243(4) . ?
O12 N24 1.226(4) . ?
O13 N24 1.226(4) . ?
O14 C18 1.336(5) . ?
O14 H14 0.67(5) . ?
O15 N25 1.249(4) . ?
O16 N25 1.249(4) . ?
O17 C20 1.340(4) . ?
O17 H17 0.79(4) . ?
O18 N26 1.224(4) . ?
O19 N26 1.211(4) . ?
N24 C17 1.457(4) . ?
N25 C19 1.411(5) . ?
N26 C21 1.461(5) . ?
C16 C17 1.435(5) . ?
C16 C21 1.438(5) . ?
C17 C18 1.370(5) . ?
C18 C19 1.435(5) . ?
C19 C20 1.436(5) . ?
C20 C21 1.367(5) . ?

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
N19 Cu1 N14 88.71(12) . . ?
N19 Cu1 N4 92.08(12) . . ?
N14 Cu1 N4 149.22(11) . . ?
N19 Cu1 N9 174.13(12) . . ?
N14 Cu1 N9 88.80(12) . . ?
N4 Cu1 N9 92.78(12) . . ?
N19 Cu1 O1 88.37(13) . . ?
N14 Cu1 O1 106.85(11) . . ?
N4 Cu1 O1 103.93(11) . . ?
N9 Cu1 O1 87.26(13) . . ?
Cu1 O1 H1A 107(4) . . ?
Cu1 O1 H1B 106(4) . . ?
H1A O1 H1B 118(5) . . ?
C1 N1 N2 110.1(3) . . ?
C1 N1 N5 131.7(3) . . ?
N2 N1 N5 118.1(3) . . ?
N3 N2 N1 106.1(3) . . ?
N2 N3 N4 109.6(3) . . ?
C1 N4 N3 107.9(3) . . ?
C1 N4 Cu1 135.8(2) . . ?
N3 N4 Cu1 116.1(2) . . ?
N1 N5 H5A 106(3) . . ?
N1 N5 H5B 106(3) . . ?
H5A N5 H5B 111(3) . . ?
C3 N6 N7 110.4(3) . . ?
C3 N6 N10 131.7(3) . . ?
N7 N6 N10 117.9(3) . . ?
N8 N7 N6 105.9(3) . . ?
N7 N8 N9 109.7(3) . . ?
C3 N9 N8 107.6(3) . . ?
C3 N9 Cu1 134.8(2) . . ?
N8 N9 Cu1 117.4(2) . . ?
N6 N10 H10A 110(3) . . ?
N6 N10 H10B 109(3) . . ?
H10A N10 H10B 111(4) . . ?
C5 N11 N12 109.6(3) . . ?
C5 N11 N15 124.8(3) . . ?
N12 N11 N15 125.6(3) . . ?
N13 N12 N11 106.6(3) . . ?
N12 N13 N14 109.2(3) . . ?
C5 N14 N13 107.4(3) . . ?
C5 N14 Cu1 132.7(2) . . ?
N13 N14 Cu1 119.9(2) . . ?
N11 N15 H15A 106(3) . . ?
N11 N15 H15B 106(3) . . ?
H15A N15 H15B 111(3) . . ?
C7 N16 N17 110.2(3) . . ?
C7 N16 N20 125.5(3) . . ?
N17 N16 N20 124.1(3) . . ?
N18 N17 N16 105.9(3) . . ?
N17 N18 N19 110.0(3) . . ?
C7 N19 N18 107.1(3) . . ?
C7 N19 Cu1 133.1(2) . . ?
N18 N19 Cu1 119.1(2) . . ?
N16 N20 H20B 111(3) . . ?
N16 N20 H20A 107(3) . . ?
H20B N20 H20A 109(5) . . ?
N4 C1 N1 106.3(3) . . ?
N4 C1 C2 128.0(3) . . ?
N1 C1 C2 125.7(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N9 C3 N6 106.4(3) . . ?
N9 C3 C4 128.3(3) . . ?
N6 C3 C4 125.3(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N14 C5 N11 107.2(3) . . ?
N14 C5 C6 128.5(3) . . ?
N11 C5 C6 124.4(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N19 C7 N16 106.8(3) . . ?
N19 C7 C8 128.3(3) . . ?
N16 C7 C8 124.8(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 O7 H7 104(4) . . ?
C15 O10 H10 102(3) . . ?
O3 N21 O2 123.9(3) . . ?
O3 N21 C10 118.8(3) . . ?
O2 N21 C10 117.4(3) . . ?
O5 N22 O6 123.3(3) . . ?
O5 N22 C12 118.1(3) . . ?
O6 N22 C12 118.6(3) . . ?
O8 N23 O9 119.7(3) . . ?
O8 N23 C14 119.9(4) . . ?
O9 N23 C14 120.4(4) . . ?
C15 C10 C11 125.3(4) . . ?
C15 C10 N21 118.8(3) . . ?
C11 C10 N21 115.9(3) . . ?
O4 C11 C12 124.2(4) . . ?
O4 C11 C10 122.3(4) . . ?
C12 C11 C10 113.5(3) . . ?
C13 C12 C11 124.0(4) . . ?
C13 C12 N22 118.9(3) . . ?
C11 C12 N22 117.2(3) . . ?
O7 C13 C12 118.0(4) . . ?
O7 C13 C14 122.5(4) . . ?
C12 C13 C14 119.6(4) . . ?
N23 C14 C13 121.1(4) . . ?
N23 C14 C15 119.9(4) . . ?
C13 C14 C15 119.0(3) . . ?
O10 C15 C10 118.5(4) . . ?
O10 C15 C14 122.8(4) . . ?
C10 C15 C14 118.6(4) . . ?
C18 O14 H14 100(5) . . ?
C20 O17 H17 105(3) . . ?
O12 N24 O13 122.8(3) . . ?
O12 N24 C17 117.5(3) . . ?
O13 N24 C17 119.7(3) . . ?
O15 N25 O16 120.7(3) . . ?
O15 N25 C19 119.4(3) . . ?
O16 N25 C19 119.9(4) . . ?
O19 N26 O18 123.8(4) . . ?
O19 N26 C21 117.5(3) . . ?
O18 N26 C21 118.6(3) . . ?
O11 C16 C17 123.7(4) . . ?
O11 C16 C21 123.5(4) . . ?
C17 C16 C21 112.8(3) . . ?
C18 C17 C16 125.1(4) . . ?
C18 C17 N24 118.1(3) . . ?
C16 C17 N24 116.8(3) . . ?
O14 C18 C17 118.5(4) . . ?
O14 C18 C19 122.5(4) . . ?
C17 C18 C19 119.0(3) . . ?
N25 C19 C18 120.7(3) . . ?
N25 C19 C20 120.3(3) . . ?
C18 C19 C20 119.0(3) . . ?
O17 C20 C21 118.8(4) . . ?
O17 C20 C19 122.5(3) . . ?
C21 C20 C19 118.6(3) . . ?
C20 C21 C16 125.5(4) . . ?
C20 C21 N26 118.7(3) . . ?
C16 C21 N26 115.8(3) . . ?

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 N1 N2 N3 0.6(4) . . . . ?
N5 N1 N2 N3 -177.5(3) . . . . ?
N1 N2 N3 N4 -0.2(4) . . . . ?
N2 N3 N4 C1 -0.3(4) . . . . ?
N2 N3 N4 Cu1 175.4(2) . . . . ?
C3 N6 N7 N8 1.5(4) . . . . ?
N10 N6 N7 N8 179.8(3) . . . . ?
N6 N7 N8 N9 -0.8(4) . . . . ?
N7 N8 N9 C3 -0.1(4) . . . . ?
N7 N8 N9 Cu1 -176.1(2) . . . . ?
C5 N11 N12 N13 0.7(4) . . . . ?
N15 N11 N12 N13 179.6(3) . . . . ?
N11 N12 N13 N14 -0.5(4) . . . . ?
N12 N13 N14 C5 0.2(4) . . . . ?
N12 N13 N14 Cu1 178.4(2) . . . . ?
C7 N16 N17 N18 -0.4(4) . . . . ?
N20 N16 N17 N18 -175.9(4) . . . . ?
N16 N17 N18 N19 0.1(4) . . . . ?
N17 N18 N19 C7 0.1(4) . . . . ?
N17 N18 N19 Cu1 171.5(2) . . . . ?
N3 N4 C1 N1 0.6(4) . . . . ?
Cu1 N4 C1 N1 -173.8(3) . . . . ?
N3 N4 C1 C2 -180.0(3) . . . . ?
Cu1 N4 C1 C2 5.6(6) . . . . ?
N2 N1 C1 N4 -0.8(4) . . . . ?
N5 N1 C1 N4 176.9(4) . . . . ?
N2 N1 C1 C2 179.8(3) . . . . ?
N5 N1 C1 C2 -2.4(6) . . . . ?
N8 N9 C3 N6 1.0(4) . . . . ?
Cu1 N9 C3 N6 176.0(2) . . . . ?
N8 N9 C3 C4 -176.9(3) . . . . ?
Cu1 N9 C3 C4 -2.0(6) . . . . ?
N7 N6 C3 N9 -1.6(4) . . . . ?
N10 N6 C3 N9 -179.6(4) . . . . ?
N7 N6 C3 C4 176.5(3) . . . . ?
N10 N6 C3 C4 -1.5(6) . . . . ?
N13 N14 C5 N11 0.2(4) . . . . ?
Cu1 N14 C5 N11 -177.7(2) . . . . ?
N13 N14 C5 C6 -179.5(4) . . . . ?
Cu1 N14 C5 C6 2.6(6) . . . . ?
N12 N11 C5 N14 -0.5(4) . . . . ?
N15 N11 C5 N14 -179.4(3) . . . . ?
N12 N11 C5 C6 179.2(3) . . . . ?
N15 N11 C5 C6 0.3(6) . . . . ?
N18 N19 C7 N16 -0.3(4) . . . . ?
Cu1 N19 C7 N16 -170.0(2) . . . . ?
N18 N19 C7 C8 178.3(3) . . . . ?
Cu1 N19 C7 C8 8.6(6) . . . . ?
N17 N16 C7 N19 0.4(4) . . . . ?
N20 N16 C7 N19 175.9(4) . . . . ?
N17 N16 C7 C8 -178.2(3) . . . . ?
N20 N16 C7 C8 -2.7(6) . . . . ?
O3 N21 C10 C15 79.7(4) . . . . ?
O2 N21 C10 C15 -101.5(4) . . . . ?
O3 N21 C10 C11 -98.2(4) . . . . ?
O2 N21 C10 C11 80.6(4) . . . . ?
C15 C10 C11 O4 -174.5(3) . . . . ?
N21 C10 C11 O4 3.2(5) . . . . ?
C15 C10 C11 C12 3.5(5) . . . . ?
N21 C10 C11 C12 -178.8(3) . . . . ?
O4 C11 C12 C13 176.4(3) . . . . ?
C10 C11 C12 C13 -1.6(5) . . . . ?
O4 C11 C12 N22 -3.0(5) . . . . ?
C10 C11 C12 N22 179.0(3) . . . . ?
O5 N22 C12 C13 125.2(4) . . . . ?
O6 N22 C12 C13 -55.8(5) . . . . ?
O5 N22 C12 C11 -55.4(4) . . . . ?
O6 N22 C12 C11 123.6(4) . . . . ?
C11 C12 C13 O7 178.7(3) . . . . ?
N22 C12 C13 O7 -1.9(5) . . . . ?
C11 C12 C13 C14 -1.1(5) . . . . ?
N22 C12 C13 C14 178.3(3) . . . . ?
O8 N23 C14 C13 -5.1(5) . . . . ?
O9 N23 C14 C13 174.8(3) . . . . ?
O8 N23 C14 C15 177.3(3) . . . . ?
O9 N23 C14 C15 -2.8(5) . . . . ?
O7 C13 C14 N23 4.8(5) . . . . ?
C12 C13 C14 N23 -175.5(3) . . . . ?
O7 C13 C14 C15 -177.6(3) . . . . ?
C12 C13 C14 C15 2.1(5) . . . . ?
C11 C10 C15 O10 178.8(3) . . . . ?
N21 C10 C15 O10 1.2(5) . . . . ?
C11 C10 C15 C14 -2.6(5) . . . . ?
N21 C10 C15 C14 179.8(3) . . . . ?
N23 C14 C15 O10 -4.2(5) . . . . ?
C13 C14 C15 O10 178.1(3) . . . . ?
N23 C14 C15 C10 177.2(3) . . . . ?
C13 C14 C15 C10 -0.4(5) . . . . ?
O11 C16 C17 C18 -175.4(3) . . . . ?
C21 C16 C17 C18 2.3(5) . . . . ?
O11 C16 C17 N24 4.0(5) . . . . ?
C21 C16 C17 N24 -178.3(3) . . . . ?
O12 N24 C17 C18 -119.8(4) . . . . ?
O13 N24 C17 C18 61.1(5) . . . . ?
O12 N24 C17 C16 60.8(4) . . . . ?
O13 N24 C17 C16 -118.3(4) . . . . ?
C16 C17 C18 O14 179.6(3) . . . . ?
N24 C17 C18 O14 0.3(5) . . . . ?
C16 C17 C18 C19 -0.8(5) . . . . ?
N24 C17 C18 C19 179.9(3) . . . . ?
O15 N25 C19 C18 5.9(5) . . . . ?
O16 N25 C19 C18 -172.8(3) . . . . ?
O15 N25 C19 C20 -175.0(3) . . . . ?
O16 N25 C19 C20 6.3(5) . . . . ?
O14 C18 C19 N25 -1.4(5) . . . . ?
C17 C18 C19 N25 179.0(3) . . . . ?
O14 C18 C19 C20 179.5(3) . . . . ?
C17 C18 C19 C20 -0.1(5) . . . . ?
N25 C19 C20 O17 2.8(5) . . . . ?
C18 C19 C20 O17 -178.0(3) . . . . ?
N25 C19 C20 C21 -180.0(3) . . . . ?
C18 C19 C20 C21 -0.9(5) . . . . ?
O17 C20 C21 C16 -179.9(3) . . . . ?
C19 C20 C21 C16 2.8(5) . . . . ?
O17 C20 C21 N26 -3.0(5) . . . . ?
C19 C20 C21 N26 179.7(3) . . . . ?
O11 C16 C21 C20 174.3(3) . . . . ?
C17 C16 C21 C20 -3.4(5) . . . . ?
O11 C16 C21 N26 -2.7(5) . . . . ?
C17 C16 C21 N26 179.6(3) . . . . ?
O19 N26 C21 C20 121.0(4) . . . . ?
O18 N26 C21 C20 -61.2(5) . . . . ?
O19 N26 C21 C16 -61.8(4) . . . . ?
O18 N26 C21 C16 115.9(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
C2 H2A O1 0.98 2.47 3.332(5) 146.5 .
C2 H2B N10 0.98 2.67 3.395(5) 131.4 2_645
C2 H2C O11 0.98 2.64 3.261(5) 121.3 2_645
C4 H4A N3 0.98 2.46 3.340(5) 148.5 .
C4 H4B O8 0.98 2.36 3.284(5) 157.6 1_455
C4 H4B O19 0.98 2.59 3.176(5) 118.2 1_455
C4 H4C O6 0.98 2.54 3.322(5) 137.2 2_655
C6 H6B N15 0.98 2.39 3.273(5) 149.7 3_666
C8 H8A N3 0.98 2.54 3.467(5) 157.8 .
O1 H1A N18 0.79(5) 2.30(5) 2.838(5) 126(4) .
O1 H1B N8 0.81(6) 2.22(6) 2.774(5) 126(5) .
N10 H10A N5 0.80(4) 2.60(4) 3.269(5) 142(4) 2
N15 H15A O4 0.83(3) 2.16(3) 2.974(4) 165(4) 4_466
N15 H15B O4 0.91(4) 2.00(4) 2.864(4) 157(4) 2_655
N20 H20B O10 0.85(5) 2.60(4) 3.343(6) 146(4) 4_466
N20 H20B O13 0.85(5) 2.55(5) 3.159(5) 129(4) 4_566
N20 H20A N17 0.78(4) 2.39(4) 3.152(5) 165(4) 3_656
N5 H5A O17 0.95(4) 2.47(4) 3.412(5) 176(3) .
N5 H5B O11 0.87(4) 2.06(4) 2.881(4) 159(4) 2_645
O7 H7 O8 0.74(4) 1.87(4) 2.550(5) 153(5) .
O7 H7 N23 0.74(4) 2.41(4) 2.874(5) 122(4) .
O10 H10 O9 0.81(4) 1.78(4) 2.531(4) 154(4) .
O10 H10 N23 0.81(4) 2.35(4) 2.858(5) 122(4) .
O17 H17 O16 0.79(4) 1.83(4) 2.547(4) 150(4) .
O17 H17 N25 0.79(4) 2.39(4) 2.872(5) 121(4) .
O14 H14 O15 0.67(5) 1.91(5) 2.541(5) 157(7) .
O14 H14 N25 0.67(5) 2.42(6) 2.875(5) 128(6) .
C2 H2A O1 0.98 2.47 3.332(5) 146.5 .
C2 H2B N10 0.98 2.67 3.395(5) 131.4 2_645
C2 H2C O11 0.98 2.64 3.261(5) 121.3 2_645
C4 H4A N3 0.98 2.46 3.340(5) 148.5 .
C4 H4B O8 0.98 2.36 3.284(5) 157.6 1_455
C4 H4B O19 0.98 2.59 3.176(5) 118.2 1_455
C4 H4C O6 0.98 2.54 3.322(5) 137.2 2_655
C6 H6B N15 0.98 2.39 3.273(5) 149.7 3_666
C8 H8A N3 0.98 2.54 3.467(5) 157.8 .
O1 H1A N18 0.79(5) 2.30(5) 2.838(5) 126(4) .
O1 H1B N8 0.81(6) 2.22(6) 2.774(5) 126(5) .
N10 H10A N5 0.80(4) 2.60(4) 3.269(5) 142(4) 2
N15 H15A O4 0.83(3) 2.16(3) 2.974(4) 165(4) 4_466
N15 H15B O4 0.91(4) 2.00(4) 2.864(4) 157(4) 2_655
N20 H20B O10 0.85(5) 2.60(4) 3.343(6) 146(4) 4_466
N20 H20B O13 0.85(5) 2.55(5) 3.159(5) 129(4) 4_566
N20 H20A N17 0.78(4) 2.39(4) 3.152(5) 165(4) 3_656
N5 H5A O17 0.95(4) 2.47(4) 3.412(5) 176(3) .
N5 H5B O11 0.87(4) 2.06(4) 2.881(4) 159(4) 2_645
O7 H7 O8 0.74(4) 1.87(4) 2.550(5) 153(5) .
O7 H7 N23 0.74(4) 2.41(4) 2.874(5) 122(4) .
O10 H10 O9 0.81(4) 1.78(4) 2.531(4) 154(4) .
O10 H10 N23 0.81(4) 2.35(4) 2.858(5) 122(4) .
O17 H17 O16 0.79(4) 1.83(4) 2.547(4) 150(4) .
O17 H17 N25 0.79(4) 2.39(4) 2.872(5) 121(4) .
O14 H14 O15 0.67(5) 1.91(5) 2.541(5) 157(7) .
O14 H14 N25 0.67(5) 2.42(6) 2.875(5) 128(6) .

_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.
;



_refine_diff_density_max         0.714
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.086

_shelxl_version_number           2013-4


####################################################################### 
# 
# 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_nx241
_database_code_depnum_ccdc_archive 'CCDC 1934800'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2018-06-27
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
di(2-amino-5-methyltetrazolyl) dipicrato copper(II)
;
_chemical_name_common            
'di(2-amino-5-methyltetrazolyl) dipicrato copper(II)'
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cu N16 O14'
_chemical_formula_sum            'C16 H14 Cu N16 O14'
_chemical_formula_weight         717.97

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_symmetry_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                   7.7928(6)
_cell_length_b                   11.1366(9)
_cell_length_c                   15.8638(12)
_cell_angle_alpha                73.445(7)
_cell_angle_beta                 81.065(6)
_cell_angle_gamma                77.470(7)
_cell_volume                     1281.80(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    2295
_cell_measurement_theta_min      4.2770
_cell_measurement_theta_max      30.1010

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.083
_exptl_absorpt_coefficient_mu    0.958
_shelx_estimated_absorpt_T_min   0.814
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79147
_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.
;

_exptl_special_details           
;
 ?
;


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_F_000             726
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_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            10367
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0881
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.109
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5012
_reflns_number_gt                3881
_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    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'enCIFer 1.5.1 (CCDC 2014)'

_refine_special_details          
;
 ?
;
_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+0.2350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5012
_refine_ls_number_parameters     442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      0.0073055000
_diffrn_orient_matrix_UB_12      0.0522316000
_diffrn_orient_matrix_UB_13      0.0155618000
_diffrn_orient_matrix_UB_21      -0.0607170000
_diffrn_orient_matrix_UB_22      0.0407869000
_diffrn_orient_matrix_UB_23      -0.0294628000
_diffrn_orient_matrix_UB_31      -0.0710036000
_diffrn_orient_matrix_UB_32      -0.0132374000
_diffrn_orient_matrix_UB_33      0.0329778000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  -5.00   0.80   33.00    --  -28.70 -60.00  48.00  105
  2  ω   -101.00 -33.80   0.80   33.00    --  -28.70-179.00  60.00   84
  3  ω   -104.00   3.20   0.80   33.00    --  -28.70 -19.00-120.00  134
  4  ω     28.00  68.00   0.80   33.00    --   29.79 -99.00  90.00   50
  5  ω    -18.00  70.00   0.80   33.00    --   29.79 -99.00-120.00  110
  6  ω     -2.00 101.20   0.80   33.00    --   29.79  77.00   0.00  129
;



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_
_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 0.35679(4) 0.01151(3) 0.25972(2) 0.01909(12) Uani 1 1 d . . . . .
O1 O 0.5006(2) -0.15326(19) 0.25931(13) 0.0201(5) Uani 1 1 d . . . . .
O2 O 0.4280(3) -0.0532(2) 0.40550(14) 0.0237(5) Uani 1 1 d . . . . .
O3 O 0.4039(3) -0.1916(2) 0.53059(15) 0.0328(6) Uani 1 1 d . . . . .
O4 O 0.5791(3) -0.3142(2) 0.15244(15) 0.0302(5) Uani 1 1 d . . . . .
O5 O 0.8548(3) -0.3960(2) 0.17033(15) 0.0333(6) Uani 1 1 d . . . . .
O6 O 0.8830(3) -0.6784(2) 0.47176(16) 0.0371(6) Uani 1 1 d . . . . .
O7 O 0.7979(4) -0.5876(3) 0.57813(18) 0.0545(8) Uani 1 1 d . . . . .
O8 O 0.2121(2) 0.17742(19) 0.25470(13) 0.0193(5) Uani 1 1 d . . . . .
O9 O 0.2595(3) 0.0706(2) 0.11116(15) 0.0281(5) Uani 1 1 d . . . . .
O10 O 0.0873(3) 0.1995(2) 0.01554(15) 0.0316(6) Uani 1 1 d . . . . .
O11 O 0.2837(3) 0.6078(2) -0.09618(16) 0.0402(6) Uani 1 1 d . . . . .
O12 O 0.3332(3) 0.7013(2) -0.00164(17) 0.0385(6) Uani 1 1 d . . . . .
O13 O 0.4265(3) 0.4343(2) 0.29976(16) 0.0332(6) Uani 1 1 d . . . . .
O14 O 0.2023(3) 0.3414(2) 0.35387(15) 0.0353(6) Uani 1 1 d . . . . .
N1 N 0.8474(3) 0.1243(2) 0.19272(17) 0.0227(6) Uani 1 1 d . . . . .
N2 N 0.7613(3) 0.1736(2) 0.25720(17) 0.0192(6) Uani 1 1 d . . . . .
N3 N 0.5992(3) 0.1569(2) 0.27945(17) 0.0222(6) Uani 1 1 d . . . . .
N4 N 0.5741(3) 0.0899(2) 0.22570(17) 0.0206(6) Uani 1 1 d . . . . .
N5 N 0.8337(4) 0.2470(3) 0.2945(2) 0.0230(6) Uani 1 1 d . . . . .
N6 N -0.0769(3) -0.1759(2) 0.34359(18) 0.0245(6) Uani 1 1 d . . . . .
N7 N -0.0787(3) -0.1064(2) 0.39915(17) 0.0213(6) Uani 1 1 d . . . . .
N8 N 0.0495(3) -0.0414(2) 0.38357(17) 0.0209(6) Uani 1 1 d . . . . .
N9 N 0.1434(3) -0.0696(2) 0.31133(17) 0.0197(6) Uani 1 1 d . . . . .
N10 N -0.2070(4) -0.1094(3) 0.4714(2) 0.0260(6) Uani 1 1 d . . . . .
N11 N 0.4533(3) -0.1648(2) 0.45137(18) 0.0219(6) Uani 1 1 d . . . . .
N12 N 0.7035(3) -0.3551(2) 0.19852(17) 0.0224(6) Uani 1 1 d . . . . .
N13 N 0.8101(4) -0.5869(3) 0.5004(2) 0.0297(7) Uani 1 1 d . . . . .
N14 N 0.1828(3) 0.1788(3) 0.07396(17) 0.0233(6) Uani 1 1 d . . . . .
N15 N 0.3031(3) 0.3877(2) 0.29173(18) 0.0245(6) Uani 1 1 d . . . . .
N16 N 0.2953(3) 0.6115(3) -0.0205(2) 0.0299(7) Uani 1 1 d . . . . .
C1 C 0.7257(4) 0.0717(3) 0.1730(2) 0.0223(7) Uani 1 1 d . . . . .
C2 C 0.7521(4) 0.0039(3) 0.1030(2) 0.0294(8) Uani 1 1 d . . . . .
H2A H 0.8555 0.0256 0.0622 0.044 Uiso 1 1 calc R U . . .
H2B H 0.6473 0.0293 0.0705 0.044 Uiso 1 1 calc R U . . .
H2C H 0.7710 -0.0882 0.1298 0.044 Uiso 1 1 calc R U . . .
C3 C 0.0666(4) -0.1520(3) 0.2887(2) 0.0228(7) Uani 1 1 d . . . . .
C4 C 0.1355(4) -0.2108(3) 0.2146(2) 0.0317(8) Uani 1 1 d . . . . .
H4A H 0.0575 -0.2673 0.2115 0.047 Uiso 1 1 calc R U . . .
H4B H 0.2545 -0.2601 0.2241 0.047 Uiso 1 1 calc R U . . .
H4C H 0.1400 -0.1438 0.1591 0.047 Uiso 1 1 calc R U . . .
C5 C 0.5655(4) -0.2497(3) 0.3179(2) 0.0184(6) Uani 1 1 d . . . . .
C6 C 0.5481(4) -0.2656(3) 0.4120(2) 0.0195(7) Uani 1 1 d . . . . .
C7 C 0.6272(4) -0.3741(3) 0.4703(2) 0.0231(7) Uani 1 1 d . . . . .
H7 H 0.6114 -0.3809 0.5320 0.028 Uiso 1 1 calc R U . . .
C8 C 0.7285(4) -0.4720(3) 0.4384(2) 0.0229(7) Uani 1 1 d . . . . .
C9 C 0.7553(4) -0.4649(3) 0.3489(2) 0.0222(7) Uani 1 1 d . . . . .
H9 H 0.8291 -0.5319 0.3273 0.027 Uiso 1 1 calc R U . . .
C10 C 0.6720(4) -0.3585(3) 0.2924(2) 0.0197(7) Uani 1 1 d . . . . .
C11 C 0.2328(4) 0.2772(3) 0.1896(2) 0.0197(7) Uani 1 1 d . . . . .
C12 C 0.2148(4) 0.2878(3) 0.1000(2) 0.0202(7) Uani 1 1 d . . . . .
C13 C 0.2257(4) 0.3966(3) 0.0321(2) 0.0229(7) Uani 1 1 d . . . . .
H13 H 0.2036 0.4010 -0.0261 0.027 Uiso 1 1 calc R U . . .
C14 C 0.2696(4) 0.4983(3) 0.0515(2) 0.0223(7) Uani 1 1 d . . . . .
C15 C 0.2973(4) 0.4955(3) 0.1360(2) 0.0229(7) Uani 1 1 d . . . . .
H15 H 0.3310 0.5657 0.1478 0.027 Uiso 1 1 calc R U . . .
C16 C 0.2749(4) 0.3879(3) 0.2027(2) 0.0199(7) Uani 1 1 d . . . . .
H5A H 0.938(5) 0.214(4) 0.296(2) 0.037(11) Uiso 1 1 d . . . . .
H10B H -0.162(6) -0.170(5) 0.515(3) 0.067(15) Uiso 1 1 d . . . . .
H5B H 0.778(5) 0.239(4) 0.352(3) 0.052(12) Uiso 1 1 d . . . . .
H10A H -0.233(5) -0.035(4) 0.481(3) 0.053(13) Uiso 1 1 d . . . . .


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 O8 1.932(2) . ?
Cu1 O1 1.933(2) . ?
Cu1 N4 2.002(2) . ?
Cu1 N9 2.014(2) . ?
Cu1 O2 2.335(2) . ?
O1 C5 1.271(3) . ?
O2 N11 1.239(3) . ?
O3 N11 1.226(3) . ?
O4 N12 1.233(3) . ?
O5 N12 1.232(3) . ?
O6 N13 1.225(3) . ?
O7 N13 1.219(4) . ?
O8 C11 1.304(3) . ?
O9 N14 1.245(3) . ?
O10 N14 1.218(3) . ?
O11 N16 1.231(4) . ?
O12 N16 1.226(4) . ?
O13 N15 1.226(3) . ?
O14 N15 1.225(3) . ?
N1 N2 1.321(4) . ?
N1 C1 1.334(4) . ?
N2 N3 1.296(3) . ?
N2 N5 1.384(4) . ?
N3 N4 1.342(4) . ?
N4 C1 1.350(4) . ?
N5 H5A 0.82(4) . ?
N5 H5B 0.93(4) . ?
N6 N7 1.326(4) . ?
N6 C3 1.332(4) . ?
N7 N8 1.311(3) . ?
N7 N10 1.396(4) . ?
N8 N9 1.339(4) . ?
N9 C3 1.350(4) . ?
N10 H10B 0.88(5) . ?
N10 H10A 0.86(5) . ?
N11 C6 1.447(4) . ?
N12 C10 1.462(4) . ?
N13 C8 1.461(4) . ?
N14 C12 1.468(4) . ?
N15 C16 1.462(4) . ?
N16 C14 1.466(4) . ?
C1 C2 1.478(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.479(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.435(4) . ?
C5 C6 1.440(4) . ?
C6 C7 1.383(4) . ?
C7 C8 1.373(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(4) . ?
C9 C10 1.368(4) . ?
C9 H9 0.9500 . ?
C11 C12 1.418(4) . ?
C11 C16 1.418(4) . ?
C12 C13 1.381(4) . ?
C13 C14 1.376(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C15 C16 1.377(4) . ?
C15 H15 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
O8 Cu1 O1 177.50(9) . . ?
O8 Cu1 N4 90.28(9) . . ?
O1 Cu1 N4 89.65(9) . . ?
O8 Cu1 N9 89.65(9) . . ?
O1 Cu1 N9 90.75(9) . . ?
N4 Cu1 N9 172.08(11) . . ?
O8 Cu1 O2 101.77(8) . . ?
O1 Cu1 O2 80.72(8) . . ?
N4 Cu1 O2 88.14(9) . . ?
N9 Cu1 O2 84.12(9) . . ?
C5 O1 Cu1 135.3(2) . . ?
N11 O2 Cu1 125.30(19) . . ?
C11 O8 Cu1 122.60(17) . . ?
N2 N1 C1 102.2(2) . . ?
N3 N2 N1 115.9(3) . . ?
N3 N2 N5 121.5(3) . . ?
N1 N2 N5 122.5(2) . . ?
N2 N3 N4 104.1(2) . . ?
N3 N4 C1 107.6(2) . . ?
N3 N4 Cu1 115.09(18) . . ?
C1 N4 Cu1 135.5(2) . . ?
N2 N5 H5A 105(3) . . ?
N2 N5 H5B 107(3) . . ?
H5A N5 H5B 110(3) . . ?
N7 N6 C3 101.7(2) . . ?
N8 N7 N6 115.9(2) . . ?
N8 N7 N10 123.7(3) . . ?
N6 N7 N10 120.3(3) . . ?
N7 N8 N9 103.6(2) . . ?
N8 N9 C3 107.9(2) . . ?
N8 N9 Cu1 118.6(2) . . ?
C3 N9 Cu1 133.6(2) . . ?
N7 N10 H10B 106(3) . . ?
N7 N10 H10A 108(3) . . ?
H10B N10 H10A 114(4) . . ?
O3 N11 O2 121.3(3) . . ?
O3 N11 C6 118.9(3) . . ?
O2 N11 C6 119.8(3) . . ?
O5 N12 O4 123.6(3) . . ?
O5 N12 C10 117.2(2) . . ?
O4 N12 C10 119.2(2) . . ?
O7 N13 O6 123.6(3) . . ?
O7 N13 C8 118.3(3) . . ?
O6 N13 C8 118.1(3) . . ?
O10 N14 O9 123.7(3) . . ?
O10 N14 C12 118.4(3) . . ?
O9 N14 C12 117.8(3) . . ?
O14 N15 O13 123.8(3) . . ?
O14 N15 C16 118.3(3) . . ?
O13 N15 C16 117.9(3) . . ?
O12 N16 O11 124.5(3) . . ?
O12 N16 C14 118.0(3) . . ?
O11 N16 C14 117.5(3) . . ?
N1 C1 N4 110.3(3) . . ?
N1 C1 C2 125.0(3) . . ?
N4 C1 C2 124.7(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N6 C3 N9 110.9(3) . . ?
N6 C3 C4 124.6(3) . . ?
N9 C3 C4 124.6(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 C10 119.9(3) . . ?
O1 C5 C6 127.5(3) . . ?
C10 C5 C6 112.6(3) . . ?
C7 C6 C5 123.0(3) . . ?
C7 C6 N11 115.3(3) . . ?
C5 C6 N11 121.6(3) . . ?
C8 C7 C6 119.5(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 121.8(3) . . ?
C7 C8 N13 119.2(3) . . ?
C9 C8 N13 119.0(3) . . ?
C10 C9 C8 117.9(3) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C5 125.1(3) . . ?
C9 C10 N12 116.1(3) . . ?
C5 C10 N12 118.7(3) . . ?
O8 C11 C12 124.5(3) . . ?
O8 C11 C16 122.2(3) . . ?
C12 C11 C16 113.2(3) . . ?
C13 C12 C11 124.4(3) . . ?
C13 C12 N14 115.3(3) . . ?
C11 C12 N14 120.3(3) . . ?
C14 C13 C12 117.8(3) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C13 C14 C15 122.2(3) . . ?
C13 C14 N16 119.1(3) . . ?
C15 C14 N16 118.7(3) . . ?
C16 C15 C14 118.0(3) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C15 C16 C11 124.2(3) . . ?
C15 C16 N15 117.1(3) . . ?
C11 C16 N15 118.7(3) . . ?

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 N1 N2 N3 0.0(3) . . . . ?
C1 N1 N2 N5 -175.1(3) . . . . ?
N1 N2 N3 N4 0.4(3) . . . . ?
N5 N2 N3 N4 175.7(2) . . . . ?
N2 N3 N4 C1 -0.7(3) . . . . ?
N2 N3 N4 Cu1 166.36(17) . . . . ?
C3 N6 N7 N8 0.3(3) . . . . ?
C3 N6 N7 N10 -176.9(3) . . . . ?
N6 N7 N8 N9 0.4(3) . . . . ?
N10 N7 N8 N9 177.5(3) . . . . ?
N7 N8 N9 C3 -0.9(3) . . . . ?
N7 N8 N9 Cu1 179.05(17) . . . . ?
Cu1 O2 N11 O3 -142.7(2) . . . . ?
Cu1 O2 N11 C6 39.4(3) . . . . ?
N2 N1 C1 N4 -0.5(3) . . . . ?
N2 N1 C1 C2 179.1(3) . . . . ?
N3 N4 C1 N1 0.8(3) . . . . ?
Cu1 N4 C1 N1 -162.4(2) . . . . ?
N3 N4 C1 C2 -178.8(3) . . . . ?
Cu1 N4 C1 C2 18.0(5) . . . . ?
N7 N6 C3 N9 -0.9(3) . . . . ?
N7 N6 C3 C4 177.4(3) . . . . ?
N8 N9 C3 N6 1.2(3) . . . . ?
Cu1 N9 C3 N6 -178.8(2) . . . . ?
N8 N9 C3 C4 -177.1(3) . . . . ?
Cu1 N9 C3 C4 2.9(5) . . . . ?
Cu1 O1 C5 C10 -178.90(19) . . . . ?
Cu1 O1 C5 C6 0.1(5) . . . . ?
O1 C5 C6 C7 -178.7(3) . . . . ?
C10 C5 C6 C7 0.3(4) . . . . ?
O1 C5 C6 N11 -2.1(5) . . . . ?
C10 C5 C6 N11 176.9(2) . . . . ?
O3 N11 C6 C7 -21.3(4) . . . . ?
O2 N11 C6 C7 156.6(3) . . . . ?
O3 N11 C6 C5 161.9(3) . . . . ?
O2 N11 C6 C5 -20.2(4) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
N11 C6 C7 C8 -176.3(3) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C6 C7 C8 N13 -179.4(3) . . . . ?
O7 N13 C8 C7 -6.2(4) . . . . ?
O6 N13 C8 C7 171.9(3) . . . . ?
O7 N13 C8 C9 173.9(3) . . . . ?
O6 N13 C8 C9 -8.0(4) . . . . ?
C7 C8 C9 C10 -2.3(5) . . . . ?
N13 C8 C9 C10 177.5(3) . . . . ?
C8 C9 C10 C5 3.3(5) . . . . ?
C8 C9 C10 N12 -179.8(3) . . . . ?
O1 C5 C10 C9 176.8(3) . . . . ?
C6 C5 C10 C9 -2.3(4) . . . . ?
O1 C5 C10 N12 0.1(4) . . . . ?
C6 C5 C10 N12 -179.1(2) . . . . ?
O5 N12 C10 C9 -40.1(4) . . . . ?
O4 N12 C10 C9 138.7(3) . . . . ?
O5 N12 C10 C5 136.9(3) . . . . ?
O4 N12 C10 C5 -44.2(4) . . . . ?
Cu1 O8 C11 C12 60.6(3) . . . . ?
Cu1 O8 C11 C16 -119.9(3) . . . . ?
O8 C11 C12 C13 175.7(3) . . . . ?
C16 C11 C12 C13 -3.8(4) . . . . ?
O8 C11 C12 N14 -4.5(4) . . . . ?
C16 C11 C12 N14 176.0(2) . . . . ?
O10 N14 C12 C13 -35.7(4) . . . . ?
O9 N14 C12 C13 142.1(3) . . . . ?
O10 N14 C12 C11 144.5(3) . . . . ?
O9 N14 C12 C11 -37.7(4) . . . . ?
C11 C12 C13 C14 4.9(4) . . . . ?
N14 C12 C13 C14 -174.9(3) . . . . ?
C12 C13 C14 C15 -1.9(4) . . . . ?
C12 C13 C14 N16 175.4(2) . . . . ?
O12 N16 C14 C13 179.5(3) . . . . ?
O11 N16 C14 C13 -3.1(4) . . . . ?
O12 N16 C14 C15 -3.1(4) . . . . ?
O11 N16 C14 C15 174.3(3) . . . . ?
C13 C14 C15 C16 -1.9(4) . . . . ?
N16 C14 C15 C16 -179.2(3) . . . . ?
C14 C15 C16 C11 3.0(4) . . . . ?
C14 C15 C16 N15 -179.4(3) . . . . ?
O8 C11 C16 C15 -179.8(3) . . . . ?
C12 C11 C16 C15 -0.3(4) . . . . ?
O8 C11 C16 N15 2.6(4) . . . . ?
C12 C11 C16 N15 -177.9(2) . . . . ?
O14 N15 C16 C15 139.8(3) . . . . ?
O13 N15 C16 C15 -40.0(4) . . . . ?
O14 N15 C16 C11 -42.4(4) . . . . ?
O13 N15 C16 C11 137.8(3) . . . . ?

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
C4 H4A O5 0.98 2.61 3.576(4) 168.8 1_455
C4 H4B O4 0.98 2.62 3.480(4) 145.9 .
C4 H4C O9 0.98 2.62 3.367(4) 133.3 .
C7 H7 O13 0.95 2.55 3.491(4) 171.5 2_656
C9 H9 N5 0.95 2.65 3.460(4) 143.5 1_545
C13 H13 O5 0.95 2.42 3.368(4) 175.8 2_655
C15 H15 O4 0.95 2.60 3.448(4) 149.0 1_565
N5 H5A O8 0.82(4) 2.12(4) 2.899(4) 159(3) 1_655
N10 H10B O6 0.88(5) 2.44(5) 3.110(4) 133(4) 2_646
N10 H10B O14 0.88(5) 2.42(5) 3.205(4) 149(4) 2_556
N5 H5B O3 0.93(4) 2.17(4) 3.071(4) 162(4) 2_656
N5 H5B O6 0.93(4) 2.64(4) 3.248(4) 124(3) 1_565
N10 H10A O2 0.86(5) 2.46(4) 3.111(4) 133(3) 2_556
N10 H10A O3 0.86(5) 2.55(5) 3.364(4) 157(4) 2_556
C4 H4A O5 0.98 2.61 3.576(4) 168.8 1_455
C4 H4B O4 0.98 2.62 3.480(4) 145.9 .
C4 H4C O9 0.98 2.62 3.367(4) 133.3 .
C7 H7 O13 0.95 2.55 3.491(4) 171.5 2_656
C9 H9 N5 0.95 2.65 3.460(4) 143.5 1_545
C13 H13 O5 0.95 2.42 3.368(4) 175.8 2_655
C15 H15 O4 0.95 2.60 3.448(4) 149.0 1_565
N5 H5A O8 0.82(4) 2.12(4) 2.899(4) 159(3) 1_655
N10 H10B O6 0.88(5) 2.44(5) 3.110(4) 133(4) 2_646
N10 H10B O14 0.88(5) 2.42(5) 3.205(4) 149(4) 2_556
N5 H5B O3 0.93(4) 2.17(4) 3.071(4) 162(4) 2_656
N5 H5B O6 0.93(4) 2.64(4) 3.248(4) 124(3) 1_565
N10 H10A O2 0.86(5) 2.46(4) 3.111(4) 133(3) 2_556
N10 H10A O3 0.86(5) 2.55(5) 3.364(4) 157(4) 2_556

_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.
;



_refine_diff_density_max         0.375
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-4


####################################################################### 
# 
# 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_nx111
_database_code_depnum_ccdc_archive 'CCDC 1934799'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2018-03-26
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
 di(1-aminotetrazolyl) dipicrato copper(II)
;
_chemical_name_common            ' di(1-aminotetrazolyl) dipicrato copper(II)'
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Cu N16 O14'
_chemical_formula_sum            'C14 H10 Cu N16 O14'
_chemical_formula_weight         689.92

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_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                   7.8960(6)
_cell_length_b                   21.2750(15)
_cell_length_c                   7.0280(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.995(8)
_cell_angle_gamma                90
_cell_volume                     1174.16(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1086
_cell_measurement_theta_min      4.5000
_cell_measurement_theta_max      22.2400

_exptl_crystal_description       platelet
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.042
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85843
_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.
;

_exptl_special_details           
;
 ?
;


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.951
_exptl_crystal_F_000             694
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_probe          x-ray
_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            7938
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_sigmaI/netI    0.1302
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.093
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2306
_reflns_number_gt                1495
_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    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'enCIFer 1.5.1 (CCDC 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+0.0867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2306
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      0.0459235000
_diffrn_orient_matrix_UB_12      0.0259538000
_diffrn_orient_matrix_UB_13      0.0425234000
_diffrn_orient_matrix_UB_21      -0.0325459000
_diffrn_orient_matrix_UB_22      0.0193573000
_diffrn_orient_matrix_UB_23      -0.0775147000
_diffrn_orient_matrix_UB_31      -0.0706125000
_diffrn_orient_matrix_UB_32      0.0079596000
_diffrn_orient_matrix_UB_33      0.0498448000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  24.00   1.00   30.00    --  -20.29 -99.00   0.00   43
  2  ω    -86.00  12.00   1.00   30.00    --  -20.29  19.00  60.00   98
  3  ω    -14.00  25.00   1.00   30.00    --  -20.29 -99.00 -90.00   39
  4  ω    -97.00 -50.00   1.00   30.00    --  -20.29 179.00  30.00   47
  5  ω    -53.00  40.00   1.00   30.00    --  -20.29  19.00 120.00   93
  6  ω     -8.00  71.00   1.00   30.00    --   21.39  77.00-120.00   79
;



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_
_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 1.0000 0.0000 1.0000 0.0215(2) Uani 1 2 d S . P . .
O1 O 0.9897(3) 0.08486(12) 0.9072(4) 0.0240(7) Uani 1 1 d . . . . .
O2 O 1.2628(4) 0.16006(13) 0.9615(4) 0.0338(8) Uani 1 1 d . . . . .
O3 O 1.1982(4) 0.24224(14) 0.7871(4) 0.0381(8) Uani 1 1 d . . . . .
O4 O 0.7269(4) 0.35582(12) 1.0298(5) 0.0363(8) Uani 1 1 d . . . . .
O5 O 0.5017(4) 0.30325(12) 1.0818(5) 0.0375(8) Uani 1 1 d . . . . .
O6 O 0.5365(4) 0.08491(13) 1.1681(5) 0.0417(9) Uani 1 1 d . . . . .
O7 O 0.7205(4) 0.02720(12) 1.0468(4) 0.0315(8) Uani 1 1 d . . . . .
N1 N 0.7472(4) -0.05992(14) 0.4901(5) 0.0213(8) Uani 1 1 d . . . . .
N2 N 0.8807(5) -0.09968(16) 0.5094(5) 0.0335(10) Uani 1 1 d . . . . .
N3 N 0.9751(5) -0.08196(16) 0.6604(6) 0.0333(10) Uani 1 1 d . . . . .
N4 N 0.9025(4) -0.03103(14) 0.7414(5) 0.0245(8) Uani 1 1 d . . . . .
N5 N 0.6122(5) -0.06493(19) 0.3447(6) 0.0262(9) Uani 1 1 d . . . . .
N6 N 0.6624(4) 0.07970(15) 1.0826(5) 0.0239(8) Uani 1 1 d . . . . .
N7 N 0.6492(4) 0.30619(15) 1.0413(5) 0.0237(8) Uani 1 1 d . . . . .
N8 N 1.1617(4) 0.19910(15) 0.8889(5) 0.0236(8) Uani 1 1 d . . . . .
C1 C 0.7600(5) -0.01880(18) 0.6319(6) 0.0236(10) Uani 1 1 d . . . . .
H1 H 0.6811 0.0137 0.6515 0.028 Uiso 1 1 calc R U . . .
C2 C 0.9114(5) 0.13368(17) 0.9536(5) 0.0185(9) Uani 1 1 d . . . . .
C3 C 0.9835(5) 0.19484(17) 0.9329(5) 0.0190(9) Uani 1 1 d . . . . .
C4 C 0.9009(5) 0.24982(18) 0.9571(5) 0.0212(9) Uani 1 1 d . . . . .
H4 H 0.9544 0.2889 0.9369 0.025 Uiso 1 1 calc R U . . .
C5 C 0.7380(5) 0.24801(17) 1.0115(5) 0.0190(9) Uani 1 1 d . . . . .
C6 C 0.6613(5) 0.19187(17) 1.0488(5) 0.0192(9) Uani 1 1 d . . . . .
H6 H 0.5512 0.1914 1.0917 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7460(5) 0.13644(17) 1.0233(6) 0.0197(9) Uani 1 1 d . . . . .
H5B H 0.643(5) -0.0566(18) 0.240(6) 0.021(12) Uiso 1 1 d . . . . .
H5A H 0.586(6) -0.104(2) 0.338(7) 0.049(16) Uiso 1 1 d . . . . .


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 O1 1.919(3) . ?
Cu1 O1 1.919(2) 3_757 ?
Cu1 N4 2.010(4) 3_757 ?
Cu1 N4 2.010(4) . ?
Cu1 O7 2.338(3) . ?
Cu1 O7 2.338(3) 3_757 ?
O1 C2 1.269(4) . ?
O2 N8 1.226(4) . ?
O3 N8 1.217(4) . ?
O4 N7 1.228(4) . ?
O5 N7 1.229(4) . ?
O6 N6 1.219(4) . ?
O7 N6 1.243(4) . ?
N1 C1 1.322(5) . ?
N1 N2 1.347(4) . ?
N1 N5 1.401(5) . ?
N2 N3 1.288(5) . ?
N3 N4 1.376(4) . ?
N4 C1 1.321(5) . ?
N5 H5B 0.82(4) . ?
N5 H5A 0.86(5) . ?
N6 C7 1.457(4) . ?
N7 C5 1.449(4) . ?
N8 C3 1.475(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.434(5) . ?
C2 C7 1.444(5) . ?
C3 C4 1.359(5) . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(5) . ?
C6 C7 1.376(5) . ?
C6 H6 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
O1 Cu1 O1 180.00(15) . 3_757 ?
O1 Cu1 N4 89.83(12) . 3_757 ?
O1 Cu1 N4 90.17(12) 3_757 3_757 ?
O1 Cu1 N4 90.17(12) . . ?
O1 Cu1 N4 89.83(12) 3_757 . ?
N4 Cu1 N4 180.0 3_757 . ?
O1 Cu1 O7 78.92(10) . . ?
O1 Cu1 O7 101.08(10) 3_757 . ?
N4 Cu1 O7 93.97(12) 3_757 . ?
N4 Cu1 O7 86.03(12) . . ?
O1 Cu1 O7 101.08(10) . 3_757 ?
O1 Cu1 O7 78.92(10) 3_757 3_757 ?
N4 Cu1 O7 86.03(12) 3_757 3_757 ?
N4 Cu1 O7 93.97(12) . 3_757 ?
O7 Cu1 O7 180.00(12) . 3_757 ?
C2 O1 Cu1 133.4(2) . . ?
N6 O7 Cu1 128.7(2) . . ?
C1 N1 N2 110.0(4) . . ?
C1 N1 N5 126.3(3) . . ?
N2 N1 N5 123.6(3) . . ?
N3 N2 N1 106.2(3) . . ?
N2 N3 N4 109.9(3) . . ?
C1 N4 N3 106.3(4) . . ?
C1 N4 Cu1 133.2(3) . . ?
N3 N4 Cu1 119.7(3) . . ?
N1 N5 H5B 111(3) . . ?
N1 N5 H5A 106(3) . . ?
H5B N5 H5A 104(4) . . ?
O6 N6 O7 121.2(3) . . ?
O6 N6 C7 118.8(3) . . ?
O7 N6 C7 119.9(3) . . ?
O4 N7 O5 123.4(3) . . ?
O4 N7 C5 118.2(3) . . ?
O5 N7 C5 118.3(3) . . ?
O3 N8 O2 124.9(3) . . ?
O3 N8 C3 117.3(3) . . ?
O2 N8 C3 117.7(3) . . ?
N4 C1 N1 107.6(3) . . ?
N4 C1 H1 126.2 . . ?
N1 C1 H1 126.2 . . ?
O1 C2 C3 120.5(3) . . ?
O1 C2 C7 127.1(3) . . ?
C3 C2 C7 112.4(3) . . ?
C4 C3 C2 124.6(3) . . ?
C4 C3 N8 117.0(3) . . ?
C2 C3 N8 118.3(3) . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 N7 119.0(3) . . ?
C4 C5 N7 119.7(3) . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C2 123.2(3) . . ?
C6 C7 N6 115.6(3) . . ?
C2 C7 N6 121.1(3) . . ?

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 N1 N2 N3 -1.0(4) . . . . ?
N5 N1 N2 N3 -178.0(4) . . . . ?
N1 N2 N3 N4 0.7(4) . . . . ?
N2 N3 N4 C1 -0.1(4) . . . . ?
N2 N3 N4 Cu1 171.0(3) . . . . ?
Cu1 O7 N6 O6 -153.6(3) . . . . ?
Cu1 O7 N6 C7 25.9(5) . . . . ?
N3 N4 C1 N1 -0.5(4) . . . . ?
Cu1 N4 C1 N1 -169.9(2) . . . . ?
N2 N1 C1 N4 1.0(4) . . . . ?
N5 N1 C1 N4 177.8(4) . . . . ?
Cu1 O1 C2 C3 149.0(3) . . . . ?
Cu1 O1 C2 C7 -33.3(6) . . . . ?
O1 C2 C3 C4 171.8(4) . . . . ?
C7 C2 C3 C4 -6.2(6) . . . . ?
O1 C2 C3 N8 -10.4(6) . . . . ?
C7 C2 C3 N8 171.6(3) . . . . ?
O3 N8 C3 C4 -36.2(5) . . . . ?
O2 N8 C3 C4 141.9(4) . . . . ?
O3 N8 C3 C2 145.9(4) . . . . ?
O2 N8 C3 C2 -36.0(5) . . . . ?
C2 C3 C4 C5 2.2(6) . . . . ?
N8 C3 C4 C5 -175.5(3) . . . . ?
C3 C4 C5 C6 2.6(6) . . . . ?
C3 C4 C5 N7 178.9(4) . . . . ?
O4 N7 C5 C6 171.4(4) . . . . ?
O5 N7 C5 C6 -6.7(6) . . . . ?
O4 N7 C5 C4 -5.0(6) . . . . ?
O5 N7 C5 C4 177.0(4) . . . . ?
C4 C5 C6 C7 -2.8(6) . . . . ?
N7 C5 C6 C7 -179.1(4) . . . . ?
C5 C6 C7 C2 -1.8(6) . . . . ?
C5 C6 C7 N6 174.6(4) . . . . ?
O1 C2 C7 C6 -172.0(4) . . . . ?
C3 C2 C7 C6 5.9(6) . . . . ?
O1 C2 C7 N6 11.8(6) . . . . ?
C3 C2 C7 N6 -170.4(4) . . . . ?
O6 N6 C7 C6 -7.9(6) . . . . ?
O7 N6 C7 C6 172.6(4) . . . . ?
O6 N6 C7 C2 168.6(4) . . . . ?
O7 N6 C7 C2 -10.9(6) . . . . ?

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
N5 H5B O7 0.82(4) 2.36(4) 3.055(5) 143(3) 1_554
N5 H5A O5 0.86(5) 2.18(5) 3.006(5) 160(4) 2_646

_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.
;



_refine_diff_density_max         0.612
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.098

_shelxl_version_number           2013-4


####################################################################### 
# 
# 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_lx541
_database_code_depnum_ccdc_archive 'CCDC 1934801'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             
;
'Thu Nov 10 18:19:58 2016'
;
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
bis(1-aminotetrazolyl) bis(trinitroresorcinato)copper(II)
;
_chemical_name_common            
'bis(1-aminotetrazolyl) bis(trinitroresorcinato)copper(II)'
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Cu N16 O16'
_chemical_formula_sum            'C14 H10 Cu N16 O16'
_chemical_formula_weight         721.92

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_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                   5.8896(3)
_cell_length_b                   19.8705(9)
_cell_length_c                   10.7979(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.962(6)
_cell_angle_gamma                90
_cell_volume                     1258.93(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1576
_cell_measurement_theta_min      4.2810
_cell_measurement_theta_max      24.1280

_exptl_crystal_description       block
_exptl_crystal_colour            yellow-green
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.982
_shelx_estimated_absorpt_T_min   0.828
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97932
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_F_000             726
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            9810
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_sigmaI/netI    0.1473
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.224
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2459
_reflns_number_gt                1771
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'enCIFer 1.5.1 (CCDC 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+0.5210P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2459
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1220
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      0.0230635000
_diffrn_orient_matrix_UB_12      0.0350327000
_diffrn_orient_matrix_UB_13      0.0007975000
_diffrn_orient_matrix_UB_21      0.1026829000
_diffrn_orient_matrix_UB_22      -0.0059702000
_diffrn_orient_matrix_UB_23      -0.0280797000
_diffrn_orient_matrix_UB_31      -0.0595147000
_diffrn_orient_matrix_UB_32      0.0032817000
_diffrn_orient_matrix_UB_33      -0.0596526000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    3.00  100.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   77.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00   75.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega   80.00  112.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932 -179.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00   46.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -57.0000  150.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega  -92.00   12.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994   19.0000  120.0000 104

#__ type_ start__ end____ width___ exp.time_
  6 omega -107.00  -44.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000  150.0000 63

;



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_
_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 1.0000 0.5000 0.5000 0.0256(2) Uani 1 2 d S . P . .
O1 O 0.7279(5) 0.43655(13) 0.5896(3) 0.0317(7) Uani 1 1 d . . . . .
O2 O 0.6636(7) 0.35956(16) 0.7217(3) 0.0557(10) Uani 1 1 d . . . . .
O3 O 1.1020(5) 0.41003(12) 0.4545(2) 0.0268(6) Uani 1 1 d . . . . .
O4 O 0.6780(7) 0.13279(16) 0.5857(4) 0.0652(12) Uani 1 1 d . . . . .
O5 O 0.9336(5) 0.09946(13) 0.4687(3) 0.0394(8) Uani 1 1 d . . . . .
O6 O 1.2296(7) 0.3136(2) 0.2120(3) 0.0801(14) Uani 1 1 d . . . . .
O7 O 1.4813(5) 0.32460(17) 0.3646(3) 0.0490(9) Uani 1 1 d . . . . .
N1 N 0.7876(6) 0.50287(15) 0.3454(3) 0.0260(7) Uani 1 1 d . . . . .
N2 N 0.8272(6) 0.54154(17) 0.2445(3) 0.0331(8) Uani 1 1 d . . . . .
N3 N 0.6622(6) 0.53389(17) 0.1591(3) 0.0311(8) Uani 1 1 d . . . . .
N4 N 0.5144(6) 0.49090(15) 0.2044(3) 0.0257(7) Uani 1 1 d . . . . .
N5 N 0.3094(7) 0.4702(2) 0.1428(4) 0.0349(9) Uani 1 1 d . . . . .
N7 N 0.7480(6) 0.37760(16) 0.6282(3) 0.0300(8) Uani 1 1 d . . . . .
N8 N 0.8314(7) 0.14488(17) 0.5206(3) 0.0361(9) Uani 1 1 d . . . . .
N9 N 1.2905(6) 0.31160(16) 0.3217(3) 0.0299(8) Uani 1 1 d . . . . .
C1 C 0.5922(8) 0.4730(2) 0.3178(4) 0.0284(10) Uani 1 1 d . . . . .
C2 C 0.8669(7) 0.32953(18) 0.5575(3) 0.0236(8) Uani 1 1 d . . . . .
C3 C 0.8050(7) 0.26314(19) 0.5712(4) 0.0257(9) Uani 1 1 d . . . . .
H3 H 0.6978 0.2516 0.6286 0.031 Uiso 1 1 calc R U . . .
C4 C 0.8983(7) 0.21333(18) 0.5016(4) 0.0272(9) Uani 1 1 d . . . . .
C5 C 1.0607(7) 0.22960(18) 0.4191(4) 0.0242(9) Uani 1 1 d . . . . .
C6 C 1.1198(6) 0.29624(18) 0.4090(3) 0.0221(8) Uani 1 1 d . . . . .
C7 C 1.0291(7) 0.35031(18) 0.4738(3) 0.0227(9) Uani 1 1 d . . . . .
O8 O 1.1676(6) 0.18532(15) 0.3502(3) 0.0447(9) Uani 1 1 d . . . . .
H1 H 0.525(8) 0.446(2) 0.362(4) 0.038(13) Uiso 1 1 d . . . . .
H8 H 1.098(11) 0.138(3) 0.376(6) 0.10(2) Uiso 1 1 d . . . . .
H5B H 0.344(9) 0.451(3) 0.081(5) 0.049(17) Uiso 1 1 d . . . . .
H5A H 0.244(10) 0.508(3) 0.118(5) 0.063(18) Uiso 1 1 d . . . . .


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 O3 1.962(2) . ?
Cu1 O3 1.962(2) 3_766 ?
Cu1 N1 1.999(3) . ?
Cu1 N1 1.999(3) 3_766 ?
Cu1 O1 2.316(3) . ?
Cu1 O1 2.316(3) 3_766 ?
O1 N7 1.245(4) . ?
O2 N7 1.218(4) . ?
O3 C7 1.285(4) . ?
O4 N8 1.216(5) . ?
O5 N8 1.245(4) . ?
O6 N9 1.208(4) . ?
O7 N9 1.206(4) . ?
N1 C1 1.306(5) . ?
N1 N2 1.369(4) . ?
N2 N3 1.289(4) . ?
N3 N4 1.342(5) . ?
N4 C1 1.318(5) . ?
N4 N5 1.390(5) . ?
N5 H5B 0.80(5) . ?
N5 H5A 0.87(5) . ?
N7 C2 1.441(5) . ?
N8 C4 1.436(5) . ?
N9 C6 1.468(5) . ?
C1 H1 0.84(4) . ?
C2 C3 1.380(5) . ?
C2 C7 1.432(5) . ?
C3 C4 1.385(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(6) . ?
C5 O8 1.343(5) . ?
C5 C6 1.376(5) . ?
C6 C7 1.412(5) . ?
O8 H8 1.08(7) . ?

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
O3 Cu1 O3 180.0 . 3_766 ?
O3 Cu1 N1 89.99(11) . . ?
O3 Cu1 N1 90.01(11) 3_766 . ?
O3 Cu1 N1 90.01(11) . 3_766 ?
O3 Cu1 N1 89.99(11) 3_766 3_766 ?
N1 Cu1 N1 180.0 . 3_766 ?
O3 Cu1 O1 81.16(10) . . ?
O3 Cu1 O1 98.84(10) 3_766 . ?
N1 Cu1 O1 87.64(12) . . ?
N1 Cu1 O1 92.36(12) 3_766 . ?
O3 Cu1 O1 98.84(10) . 3_766 ?
O3 Cu1 O1 81.16(10) 3_766 3_766 ?
N1 Cu1 O1 92.36(12) . 3_766 ?
N1 Cu1 O1 87.64(12) 3_766 3_766 ?
O1 Cu1 O1 180.00(12) . 3_766 ?
N7 O1 Cu1 127.1(2) . . ?
C7 O3 Cu1 133.4(3) . . ?
C1 N1 N2 106.3(3) . . ?
C1 N1 Cu1 130.8(3) . . ?
N2 N1 Cu1 122.9(3) . . ?
N3 N2 N1 109.5(3) . . ?
N2 N3 N4 106.7(3) . . ?
C1 N4 N3 109.0(3) . . ?
C1 N4 N5 125.7(4) . . ?
N3 N4 N5 125.3(3) . . ?
N4 N5 H5B 105(4) . . ?
N4 N5 H5A 104(4) . . ?
H5B N5 H5A 107(5) . . ?
O2 N7 O1 121.4(3) . . ?
O2 N7 C2 119.7(3) . . ?
O1 N7 C2 118.9(3) . . ?
O4 N8 O5 122.0(4) . . ?
O4 N8 C4 119.8(4) . . ?
O5 N8 C4 118.3(4) . . ?
O7 N9 O6 123.8(4) . . ?
O7 N9 C6 117.7(3) . . ?
O6 N9 C6 118.4(4) . . ?
N1 C1 N4 108.6(4) . . ?
N1 C1 H1 128(3) . . ?
N4 C1 H1 124(3) . . ?
C3 C2 C7 122.7(3) . . ?
C3 C2 N7 115.6(4) . . ?
C7 C2 N7 121.6(3) . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 N8 118.2(4) . . ?
C5 C4 N8 121.4(4) . . ?
O8 C5 C6 116.9(4) . . ?
O8 C5 C4 125.4(4) . . ?
C6 C5 C4 117.7(3) . . ?
C5 C6 C7 125.7(4) . . ?
C5 C6 N9 116.3(3) . . ?
C7 C6 N9 118.0(3) . . ?
O3 C7 C6 118.5(4) . . ?
O3 C7 C2 128.2(3) . . ?
C6 C7 C2 113.3(3) . . ?
C5 O8 H8 103(4) . . ?

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 N1 N2 N3 -1.1(4) . . . . ?
Cu1 N1 N2 N3 -179.6(2) . . . . ?
N1 N2 N3 N4 0.6(4) . . . . ?
N2 N3 N4 C1 0.2(4) . . . . ?
N2 N3 N4 N5 178.4(4) . . . . ?
Cu1 O1 N7 O2 142.4(3) . . . . ?
Cu1 O1 N7 C2 -39.8(4) . . . . ?
N2 N1 C1 N4 1.1(4) . . . . ?
Cu1 N1 C1 N4 179.5(2) . . . . ?
N3 N4 C1 N1 -0.8(4) . . . . ?
N5 N4 C1 N1 -179.1(4) . . . . ?
O2 N7 C2 C3 24.1(5) . . . . ?
O1 N7 C2 C3 -153.7(4) . . . . ?
O2 N7 C2 C7 -159.2(4) . . . . ?
O1 N7 C2 C7 23.0(5) . . . . ?
C7 C2 C3 C4 -0.7(6) . . . . ?
N7 C2 C3 C4 176.0(3) . . . . ?
C2 C3 C4 C5 1.6(6) . . . . ?
C2 C3 C4 N8 179.0(3) . . . . ?
O4 N8 C4 C3 8.1(6) . . . . ?
O5 N8 C4 C3 -172.1(3) . . . . ?
O4 N8 C4 C5 -174.6(4) . . . . ?
O5 N8 C4 C5 5.2(6) . . . . ?
C3 C4 C5 O8 177.8(4) . . . . ?
N8 C4 C5 O8 0.5(6) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
N8 C4 C5 C6 -178.2(3) . . . . ?
O8 C5 C6 C7 -179.6(3) . . . . ?
C4 C5 C6 C7 -0.7(6) . . . . ?
O8 C5 C6 N9 1.2(5) . . . . ?
C4 C5 C6 N9 -180.0(3) . . . . ?
O7 N9 C6 C5 -104.9(4) . . . . ?
O6 N9 C6 C5 78.6(5) . . . . ?
O7 N9 C6 C7 75.8(5) . . . . ?
O6 N9 C6 C7 -100.7(5) . . . . ?
Cu1 O3 C7 C6 169.1(2) . . . . ?
Cu1 O3 C7 C2 -12.9(6) . . . . ?
C5 C6 C7 O3 179.9(3) . . . . ?
N9 C6 C7 O3 -0.9(5) . . . . ?
C5 C6 C7 C2 1.6(5) . . . . ?
N9 C6 C7 C2 -179.2(3) . . . . ?
C3 C2 C7 O3 -178.9(4) . . . . ?
N7 C2 C7 O3 4.6(6) . . . . ?
C3 C2 C7 C6 -0.8(5) . . . . ?
N7 C2 C7 C6 -177.3(3) . . . . ?

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
C1 H1 O1 0.84(4) 2.64(4) 3.062(5) 112(3) .
C1 H1 O7 0.84(4) 2.42(4) 3.072(5) 135(4) 1_455
O8 H8 O5 1.08(7) 1.64(7) 2.598(4) 145(6) .
O8 H8 N2 1.08(7) 2.37(6) 3.036(4) 119(5) 2_745
O8 H8 N3 1.08(7) 2.54(6) 3.176(4) 117(5) 2_745
O8 H8 N8 1.08(7) 2.32(7) 2.929(5) 114(4) .
N5 H5B O4 0.80(5) 2.58(5) 3.085(6) 122(4) 4_565
N5 H5B N3 0.80(5) 2.61(5) 3.280(5) 142(4) 3_665
N5 H5A O5 0.87(5) 2.27(6) 3.129(5) 173(5) 2_655
C1 H1 O1 0.84(4) 2.64(4) 3.062(5) 112(3) .
C1 H1 O7 0.84(4) 2.42(4) 3.072(5) 135(4) 1_455
O8 H8 O5 1.08(7) 1.64(7) 2.598(4) 145(6) .
O8 H8 N2 1.08(7) 2.37(6) 3.036(4) 119(5) 2_745
O8 H8 N3 1.08(7) 2.54(6) 3.176(4) 117(5) 2_745
O8 H8 N8 1.08(7) 2.32(7) 2.929(5) 114(4) .
N5 H5B O4 0.80(5) 2.58(5) 3.085(6) 122(4) 4_565
N5 H5B N3 0.80(5) 2.61(5) 3.280(5) 142(4) 3_665
N5 H5A O5 0.87(5) 2.27(6) 3.129(5) 173(5) 2_655

_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.
;



_refine_diff_density_max         0.806
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-4


####################################################################### 
# 
# 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_nx246
_database_code_depnum_ccdc_archive 'CCDC 1934802'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2018-06-29
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
monoaqua 2-amino-5-methyltetrazolyl trinitroresorcinato copper(II) hydrate
;
_chemical_name_common            
;
monoaqua 2-amino-5-methyltetrazolyl trinitroresorcinato copper(II) hydrate
;
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 Cu N8 O9, H2 O'
_chemical_formula_sum            'C8 H10 Cu N8 O10'
_chemical_formula_weight         441.78

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_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                   11.7176(5)
_cell_length_b                   8.0996(3)
_cell_length_c                   16.7581(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.825(5)
_cell_angle_gamma                90
_cell_volume                     1505.40(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    3095
_cell_measurement_theta_min      4.3710
_cell_measurement_theta_max      30.5980

_exptl_crystal_description       rod
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.109
_exptl_absorpt_coefficient_mu    1.531
_shelx_estimated_absorpt_T_min   0.515
_shelx_estimated_absorpt_T_max   0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86423
_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.
;

_exptl_special_details           
;
 ?
;


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.949
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_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            11264
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.294
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2943
_reflns_number_gt                2494
_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    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'enCIFer 1.5.1 (CCDC 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+1.7061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2943
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      -0.0638956000
_diffrn_orient_matrix_UB_12      -0.0032583000
_diffrn_orient_matrix_UB_13      -0.0148012000
_diffrn_orient_matrix_UB_21      -0.0000479000
_diffrn_orient_matrix_UB_22      -0.0185623000
_diffrn_orient_matrix_UB_23      0.0413719000
_diffrn_orient_matrix_UB_31      -0.0024713000
_diffrn_orient_matrix_UB_32      0.0854936000
_diffrn_orient_matrix_UB_33      0.0084137000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     15.00  41.00   1.00    8.00    --   29.79-113.00-116.00   26
  2  ω     56.00  82.00   1.00    8.00    --   29.79-113.00-116.00   26
  3  ω    -19.00  53.00   1.00    8.00    --   29.79 -99.00-180.00   72
  4  ω   -100.00  40.00   1.00    8.00    --  -28.70   0.00 -30.00  140
  5  ω     60.00 108.00   1.00    8.00    --   29.79 179.00-180.00   48
  6  ω   -101.00   4.00   1.00    8.00    --  -28.70 -77.00 -30.00  105
  7  ω   -109.00 -62.00   1.00    8.00    --  -28.70-179.00 150.00   47
;



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_
_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 0.19419(3) 0.84707(4) 0.17405(2) 0.01507(11) Uani 1 1 d . . . . .
O1 O 0.35711(16) 0.7740(2) 0.23404(12) 0.0174(4) Uani 1 1 d . . . . .
O2 O 0.25008(17) 0.7819(3) 0.05931(13) 0.0262(5) Uani 1 1 d . . . . .
O3 O 0.3586(2) 0.7237(3) -0.01766(14) 0.0391(6) Uani 1 1 d . . . . .
O7 O 0.5920(2) 0.8386(3) 0.39443(14) 0.0360(6) Uani 1 1 d . . . . .
O8 O 0.5347(2) 0.5874(3) 0.39713(13) 0.0326(5) Uani 1 1 d . . . . .
O5 O 0.82715(16) 0.4505(2) 0.20099(12) 0.0211(4) Uani 1 1 d . . . . .
O6 O 0.74925(15) 0.5743(2) 0.32623(11) 0.0158(4) Uani 1 1 d . . . . .
O9 O 0.03281(17) 0.9329(3) 0.11182(14) 0.0237(5) Uani 1 1 d . . . . .
N1 N 0.0962(2) 0.3659(3) 0.21641(14) 0.0184(5) Uani 1 1 d . . . . .
N2 N 0.03768(19) 0.4021(3) 0.13650(14) 0.0168(5) Uani 1 1 d . . . . .
N3 N 0.05514(19) 0.5513(3) 0.11255(14) 0.0178(5) Uani 1 1 d . . . . .
N4 N 0.13114(19) 0.6194(3) 0.18124(14) 0.0171(5) Uani 1 1 d . . . . .
N5 N -0.0379(2) 0.2871(3) 0.08328(18) 0.0212(5) Uani 1 1 d . . . . .
N6 N 0.3485(2) 0.7411(3) 0.05226(15) 0.0192(5) Uani 1 1 d . . . . .
N8 N 0.55926(19) 0.7053(3) 0.36084(14) 0.0182(5) Uani 1 1 d . . . . .
C7 C 0.6586(2) 0.6189(3) 0.26187(17) 0.0149(5) Uani 1 1 d . . . . .
C1 C 0.1555(2) 0.5058(3) 0.24401(17) 0.0184(6) Uani 1 1 d . . . . .
C2 C 0.2374(3) 0.5307(4) 0.33151(18) 0.0250(6) Uani 1 1 d . . . . .
H2A H 0.2091 0.4645 0.3704 0.037 Uiso 1 1 calc R U . . .
H2B H 0.2378 0.6477 0.3465 0.037 Uiso 1 1 calc R U . . .
H2C H 0.3192 0.4964 0.3354 0.037 Uiso 1 1 calc R U . . .
C3 C 0.4461(2) 0.7285(3) 0.21006(17) 0.0145(5) Uani 1 1 d . . . . .
C4 C 0.4507(2) 0.7107(3) 0.12589(16) 0.0149(5) Uani 1 1 d . . . . .
C5 C 0.5537(2) 0.6563(3) 0.11039(17) 0.0171(6) Uani 1 1 d . . . . .
H5 H 0.5550 0.6518 0.0541 0.021 Uiso 1 1 calc R U . . .
C8 C 0.5550(2) 0.6858(3) 0.27279(16) 0.0155(5) Uani 1 1 d . . . . .
N7 N 0.7532(2) 0.5441(3) 0.15226(15) 0.0195(5) Uani 1 1 d . . . . .
C6 C 0.6539(2) 0.6088(3) 0.17538(17) 0.0162(5) Uani 1 1 d . . . . .
O4 O 0.7609(2) 0.5793(3) 0.08301(14) 0.0375(6) Uani 1 1 d . . . . .
O10 O 0.1500(2) 0.1963(3) 0.00955(16) 0.0305(5) Uani 1 1 d . . . . .
H5A H -0.031(3) 0.300(4) 0.034(2) 0.027(9) Uiso 1 1 d . . . . .
H5B H -0.109(4) 0.316(5) 0.077(3) 0.051(12) Uiso 1 1 d . . . . .
H9A H 0.027(3) 1.028(5) 0.109(2) 0.045(12) Uiso 1 1 d . . . . .
H9B H -0.024(3) 0.890(5) 0.072(2) 0.042(11) Uiso 1 1 d . . . . .
H10A H 0.189(3) 0.151(4) 0.053(3) 0.038(11) Uiso 1 1 d . . . . .
H10B H 0.194(4) 0.247(5) -0.004(3) 0.043(13) Uiso 1 1 d . . . . .


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 O1 1.9409(18) . ?
Cu1 O6 1.9567(17) 2_655 ?
Cu1 O9 1.968(2) . ?
Cu1 N4 2.005(2) . ?
Cu1 O2 2.284(2) . ?
Cu1 O5 2.3425(19) 2_655 ?
O1 C3 1.287(3) . ?
O2 N6 1.241(3) . ?
O3 N6 1.223(3) . ?
O7 N8 1.221(3) . ?
O8 N8 1.215(3) . ?
O5 N7 1.239(3) . ?
O5 Cu1 2.3425(19) 2_645 ?
O6 C7 1.297(3) . ?
O6 Cu1 1.9567(17) 2_645 ?
O9 H9A 0.77(4) . ?
O9 H9B 0.85(4) . ?
N1 N2 1.325(3) . ?
N1 C1 1.332(3) . ?
N2 N3 1.310(3) . ?
N2 N5 1.392(3) . ?
N3 N4 1.327(3) . ?
N4 C1 1.357(3) . ?
N5 H5A 0.87(4) . ?
N5 H5B 0.84(4) . ?
N6 C4 1.436(3) . ?
N8 C8 1.469(3) . ?
C7 C8 1.394(4) . ?
C7 C6 1.435(4) . ?
C1 C2 1.484(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C8 1.410(3) . ?
C3 C4 1.436(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9500 . ?
N7 O4 1.226(3) . ?
N7 C6 1.438(3) . ?
O10 H10A 0.81(4) . ?
O10 H10B 0.75(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
O1 Cu1 O6 90.62(7) . 2_655 ?
O1 Cu1 O9 176.78(8) . . ?
O6 Cu1 O9 86.26(8) 2_655 . ?
O1 Cu1 N4 90.47(8) . . ?
O6 Cu1 N4 175.65(9) 2_655 . ?
O9 Cu1 N4 92.70(9) . . ?
O1 Cu1 O2 82.19(7) . . ?
O6 Cu1 O2 91.50(8) 2_655 . ?
O9 Cu1 O2 97.07(8) . . ?
N4 Cu1 O2 92.82(9) . . ?
O1 Cu1 O5 90.97(7) . 2_655 ?
O6 Cu1 O5 78.44(7) 2_655 2_655 ?
O9 Cu1 O5 89.19(8) . 2_655 ?
N4 Cu1 O5 97.33(8) . 2_655 ?
O2 Cu1 O5 167.82(7) . 2_655 ?
C3 O1 Cu1 133.36(17) . . ?
N6 O2 Cu1 132.00(17) . . ?
N7 O5 Cu1 123.66(16) . 2_645 ?
C7 O6 Cu1 116.55(15) . 2_645 ?
Cu1 O9 H9A 116(3) . . ?
Cu1 O9 H9B 130(2) . . ?
H9A O9 H9B 109(4) . . ?
N2 N1 C1 101.8(2) . . ?
N3 N2 N1 115.6(2) . . ?
N3 N2 N5 123.4(2) . . ?
N1 N2 N5 120.9(2) . . ?
N2 N3 N4 104.2(2) . . ?
N3 N4 C1 107.8(2) . . ?
N3 N4 Cu1 119.17(17) . . ?
C1 N4 Cu1 132.93(18) . . ?
N2 N5 H5A 108(2) . . ?
N2 N5 H5B 107(3) . . ?
H5A N5 H5B 104(3) . . ?
O3 N6 O2 120.1(2) . . ?
O3 N6 C4 119.5(2) . . ?
O2 N6 C4 120.4(2) . . ?
O8 N8 O7 123.6(2) . . ?
O8 N8 C8 118.8(2) . . ?
O7 N8 C8 117.5(2) . . ?
O6 C7 C8 120.9(2) . . ?
O6 C7 C6 125.3(2) . . ?
C8 C7 C6 113.8(2) . . ?
N1 C1 N4 110.6(2) . . ?
N1 C1 C2 123.9(2) . . ?
N4 C1 C2 125.5(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 C8 117.9(2) . . ?
O1 C3 C4 128.8(2) . . ?
C8 C3 C4 113.3(2) . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 N6 115.4(2) . . ?
C3 C4 N6 122.8(2) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C7 C8 C3 127.9(2) . . ?
C7 C8 N8 115.1(2) . . ?
C3 C8 N8 116.9(2) . . ?
O4 N7 O5 121.1(2) . . ?
O4 N7 C6 118.9(2) . . ?
O5 N7 C6 120.0(2) . . ?
C5 C6 C7 121.9(2) . . ?
C5 C6 N7 116.6(2) . . ?
C7 C6 N7 121.5(2) . . ?
H10A O10 H10B 106(4) . . ?

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 N1 N2 N3 -0.3(3) . . . . ?
C1 N1 N2 N5 -179.6(2) . . . . ?
N1 N2 N3 N4 0.3(3) . . . . ?
N5 N2 N3 N4 179.6(2) . . . . ?
N2 N3 N4 C1 -0.2(3) . . . . ?
N2 N3 N4 Cu1 176.07(16) . . . . ?
Cu1 O2 N6 O3 -174.49(19) . . . . ?
Cu1 O2 N6 C4 6.8(4) . . . . ?
Cu1 O6 C7 C8 125.6(2) 2_645 . . . ?
Cu1 O6 C7 C6 -55.7(3) 2_645 . . . ?
N2 N1 C1 N4 0.1(3) . . . . ?
N2 N1 C1 C2 -179.4(3) . . . . ?
N3 N4 C1 N1 0.0(3) . . . . ?
Cu1 N4 C1 N1 -175.50(18) . . . . ?
N3 N4 C1 C2 179.6(3) . . . . ?
Cu1 N4 C1 C2 4.0(4) . . . . ?
Cu1 O1 C3 C8 178.60(17) . . . . ?
Cu1 O1 C3 C4 -2.9(4) . . . . ?
O1 C3 C4 C5 -178.5(2) . . . . ?
C8 C3 C4 C5 0.1(3) . . . . ?
O1 C3 C4 N6 -1.1(4) . . . . ?
C8 C3 C4 N6 177.5(2) . . . . ?
O3 N6 C4 C5 -2.5(3) . . . . ?
O2 N6 C4 C5 176.2(2) . . . . ?
O3 N6 C4 C3 180.0(2) . . . . ?
O2 N6 C4 C3 -1.3(4) . . . . ?
C3 C4 C5 C6 3.5(4) . . . . ?
N6 C4 C5 C6 -174.1(2) . . . . ?
O6 C7 C8 C3 -174.8(2) . . . . ?
C6 C7 C8 C3 6.3(4) . . . . ?
O6 C7 C8 N8 1.7(3) . . . . ?
C6 C7 C8 N8 -177.2(2) . . . . ?
O1 C3 C8 C7 173.4(2) . . . . ?
C4 C3 C8 C7 -5.3(4) . . . . ?
O1 C3 C8 N8 -3.1(3) . . . . ?
C4 C3 C8 N8 178.2(2) . . . . ?
O8 N8 C8 C7 -83.6(3) . . . . ?
O7 N8 C8 C7 93.6(3) . . . . ?
O8 N8 C8 C3 93.3(3) . . . . ?
O7 N8 C8 C3 -89.4(3) . . . . ?
Cu1 O5 N7 O4 -171.29(19) 2_645 . . . ?
Cu1 O5 N7 C6 6.5(3) 2_645 . . . ?
C4 C5 C6 C7 -2.4(4) . . . . ?
C4 C5 C6 N7 176.1(2) . . . . ?
O6 C7 C6 C5 179.0(2) . . . . ?
C8 C7 C6 C5 -2.1(4) . . . . ?
O6 C7 C6 N7 0.7(4) . . . . ?
C8 C7 C6 N7 179.5(2) . . . . ?
O4 N7 C6 C5 22.0(4) . . . . ?
O5 N7 C6 C5 -155.9(2) . . . . ?
O4 N7 C6 C7 -159.6(3) . . . . ?
O5 N7 C6 C7 22.5(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
C2 H2B O3 0.98 2.49 3.170(4) 126.4 4_576
C2 H2B O5 0.98 2.61 3.488(3) 148.4 2_655
C2 H2C O8 0.98 2.51 3.330(4) 140.9 .
N5 H5A N3 0.87(4) 2.66(4) 3.478(4) 157(3) 3_565
N5 H5A O10 0.87(4) 2.44(3) 2.944(4) 118(3) .
N5 H5B O2 0.84(4) 2.47(4) 2.893(3) 112(3) 3_565
N5 H5B O4 0.84(4) 2.64(4) 3.340(3) 141(3) 1_455
O9 H9A N5 0.77(4) 2.23(4) 2.981(3) 166(4) 1_565
O9 H9B O10 0.85(4) 1.80(4) 2.647(3) 176(4) 3_565
O10 H10A O6 0.81(4) 2.02(4) 2.801(3) 162(4) 2_645
O10 H10B O4 0.75(4) 2.12(4) 2.801(3) 153(4) 3_665
C2 H2B O3 0.98 2.49 3.170(4) 126.4 4_576
C2 H2B O5 0.98 2.61 3.488(3) 148.4 2_655
C2 H2C O8 0.98 2.51 3.330(4) 140.9 .
N5 H5A N3 0.87(4) 2.66(4) 3.478(4) 157(3) 3_565
N5 H5A O10 0.87(4) 2.44(3) 2.944(4) 118(3) .
N5 H5B O2 0.84(4) 2.47(4) 2.893(3) 112(3) 3_565
N5 H5B O4 0.84(4) 2.64(4) 3.340(3) 141(3) 1_455
O9 H9A N5 0.77(4) 2.23(4) 2.981(3) 166(4) 1_565
O9 H9B O10 0.85(4) 1.80(4) 2.647(3) 176(4) 3_565
O10 H10A O6 0.81(4) 2.02(4) 2.801(3) 162(4) 2_645
O10 H10B O4 0.75(4) 2.12(4) 2.801(3) 153(4) 3_665

_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.
;



_refine_diff_density_max         0.415
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-4


####################################################################### 
# 
# 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_nx243
_database_code_depnum_ccdc_archive 'CCDC 1934806'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_vrf_PLAT430_nx243               
; 
PROBLEM: Short Inter D...A Contact  O18 ..N1   2.81 Ang.  
            -1/2+x,1/2-y,-1/2+z  =      4_565 Check 
RESPONSE: These are classical nitro-nitro interaction of the picrate anion 
;
_audit_creation_date             2018-06-28
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
di(1-amino-5-methyltetrazolyl) dipicrato copper(II) semihydrate
;
_chemical_name_common            
'di(1-amino-5-methyltetrazolyl) dipicrato copper(II) semihydrate'
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H14 Cu N16 O14), H2 O'
_chemical_formula_sum            'C32 H30 Cu2 N32 O29'
_chemical_formula_weight         1453.96

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_symmetry_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                   16.5743(8)
_cell_length_b                   15.0908(7)
_cell_length_c                   22.2088(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.280(4)
_cell_angle_gamma                90
_cell_volume                     5406.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    3351
_cell_measurement_theta_min      4.3870
_cell_measurement_theta_max      25.0670

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.171
_exptl_absorpt_coefficient_mu    0.911
_shelx_estimated_absorpt_T_min   0.726
_shelx_estimated_absorpt_T_max   0.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94737
_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.
;

_exptl_special_details           
;
 ?
;


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_F_000             2944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_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            29193
_diffrn_reflns_av_unetI/netI     0.1085
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_sigmaI/netI    0.1368
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         4.159
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             10570
_reflns_number_gt                6322
_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    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'enCIFer 1.5.1 (CCDC 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         10570
_refine_ls_number_parameters     911
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      -0.0245185000
_diffrn_orient_matrix_UB_12      0.0073354000
_diffrn_orient_matrix_UB_13      0.0218349000
_diffrn_orient_matrix_UB_21      0.0158851000
_diffrn_orient_matrix_UB_22      0.0437109000
_diffrn_orient_matrix_UB_23      0.0049540000
_diffrn_orient_matrix_UB_31      -0.0328542000
_diffrn_orient_matrix_UB_32      0.0156537000
_diffrn_orient_matrix_UB_33      -0.0239958000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  94.00   1.00   10.00    --   21.39  77.00-180.00  106
  2  ω    -12.00  94.00   1.00   10.00    --   21.39  77.00  60.00  106
  3  ω    -12.00  93.00   1.00   10.00    --   21.39  77.00 -60.00  105
;



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_
_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 0.25073(3) 0.19140(4) 0.62626(2) 0.02306(15) Uani 1 1 d . . . . .
O1 O 0.32585(19) 0.15547(19) 0.57420(13) 0.0256(7) Uani 1 1 d . . . . .
O2 O 0.3311(2) 0.3249(2) 0.61354(14) 0.0310(8) Uani 1 1 d . . . . .
O3 O 0.3153(3) 0.4284(2) 0.54494(15) 0.0511(11) Uani 1 1 d . . . . .
O4 O 0.3467(2) 0.3836(2) 0.34296(15) 0.0375(9) Uani 1 1 d . . . . .
O5 O 0.3625(2) 0.2520(2) 0.30946(16) 0.0527(11) Uani 1 1 d . . . . .
O8 O 0.17094(18) 0.23838(18) 0.55517(13) 0.0235(7) Uani 1 1 d . . . . .
O9 O 0.1753(2) 0.0629(2) 0.59022(14) 0.0322(8) Uani 1 1 d . . . . .
O11 O 0.0828(2) 0.0196(2) 0.30977(13) 0.0331(8) Uani 1 1 d . . . . .
O12 O 0.0768(2) 0.1532(2) 0.27321(14) 0.0362(9) Uani 1 1 d . . . . .
O13 O 0.1521(2) 0.4002(2) 0.41378(15) 0.0368(9) Uani 1 1 d . . . . .
O14 O 0.1092(3) 0.3863(2) 0.49814(17) 0.0571(12) Uani 1 1 d . . . . .
N1 N 0.4338(2) 0.1117(2) 0.77277(16) 0.0208(8) Uani 1 1 d . . . . .
N2 N 0.4105(3) 0.1898(3) 0.79336(17) 0.0331(10) Uani 1 1 d . . . . .
N3 N 0.3515(3) 0.2199(3) 0.74994(17) 0.0344(10) Uani 1 1 d . . . . .
N4 N 0.3362(2) 0.1622(2) 0.70119(16) 0.0271(9) Uani 1 1 d . . . . .
N5 N 0.4974(3) 0.0588(3) 0.8058(2) 0.0283(10) Uani 1 1 d . . . . .
N6 N 0.0883(2) 0.2506(2) 0.73439(15) 0.0198(8) Uani 1 1 d . . . . .
N7 N 0.0997(2) 0.1626(2) 0.74427(16) 0.0278(9) Uani 1 1 d . . . . .
N8 N 0.1478(3) 0.1376(2) 0.70974(17) 0.0314(10) Uani 1 1 d . . . . .
N9 N 0.1683(2) 0.2087(2) 0.67807(15) 0.0243(9) Uani 1 1 d . . . . .
N10 N 0.0425(3) 0.3035(3) 0.7663(2) 0.0273(10) Uani 1 1 d . . . . .
N11 N 0.3261(2) 0.3509(3) 0.55993(18) 0.0298(10) Uani 1 1 d . . . . .
N12 N 0.3523(2) 0.3035(3) 0.35028(18) 0.0316(10) Uani 1 1 d . . . . .
N13 N 0.3530(3) 0.0456(3) 0.4820(2) 0.0364(11) Uani 1 1 d . . . . .
N14 N 0.1447(3) 0.0463(3) 0.53629(19) 0.0446(12) Uani 1 1 d . . . . .
N15 N 0.0886(2) 0.1004(3) 0.31658(17) 0.0265(9) Uani 1 1 d . . . . .
N16 N 0.1320(2) 0.3550(2) 0.45390(18) 0.0297(10) Uani 1 1 d . . . . .
C1 C 0.3881(3) 0.0953(3) 0.71597(19) 0.0214(10) Uani 1 1 d . . . . .
C2 C 0.3979(3) 0.0170(3) 0.6783(2) 0.0291(12) Uani 1 1 d . . . . .
H2A H 0.3432 -0.0034 0.6556 0.044 Uiso 1 1 calc R U . . .
H2B H 0.4255 -0.0305 0.7055 0.044 Uiso 1 1 calc R U . . .
H2C H 0.4315 0.0329 0.6489 0.044 Uiso 1 1 calc R U . . .
C3 C 0.1301(3) 0.2790(3) 0.69316(19) 0.0198(10) Uani 1 1 d . . . . .
C4 C 0.1321(3) 0.3695(3) 0.6703(2) 0.0277(11) Uani 1 1 d . . . . .
H4A H 0.1813 0.4000 0.6942 0.042 Uiso 1 1 calc R U . . .
H4B H 0.0821 0.4011 0.6748 0.042 Uiso 1 1 calc R U . . .
H4C H 0.1341 0.3681 0.6265 0.042 Uiso 1 1 calc R U . . .
C5 C 0.3352(3) 0.1942(3) 0.5249(2) 0.0210(10) Uani 1 1 d . . . . .
C6 C 0.3336(3) 0.2866(3) 0.5126(2) 0.0208(10) Uani 1 1 d . . . . .
C7 C 0.3394(3) 0.3213(3) 0.4561(2) 0.0258(11) Uani 1 1 d . . . . .
H7 H 0.3380 0.3836 0.4500 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3471(3) 0.2658(3) 0.4093(2) 0.0224(10) Uani 1 1 d . . . . .
C9 C 0.3522(3) 0.1750(3) 0.4178(2) 0.0265(11) Uani 1 1 d . . . . .
H9 H 0.3592 0.1369 0.3853 0.032 Uiso 1 1 calc R U . . .
C10 C 0.3469(3) 0.1414(3) 0.4736(2) 0.0240(11) Uani 1 1 d . . . . .
C11 C 0.1480(3) 0.2041(3) 0.5016(2) 0.0214(10) Uani 1 1 d . . . . .
C12 C 0.1384(3) 0.1119(3) 0.48730(19) 0.0247(11) Uani 1 1 d . . . . .
C13 C 0.1193(3) 0.0783(3) 0.4281(2) 0.0270(11) Uani 1 1 d . . . . .
H13 H 0.1126 0.0163 0.4211 0.032 Uiso 1 1 calc R U . . .
C14 C 0.1101(3) 0.1361(3) 0.37934(19) 0.0198(10) Uani 1 1 d . . . . .
C15 C 0.1158(3) 0.2259(3) 0.38793(19) 0.0234(10) Uani 1 1 d . . . . .
H15 H 0.1087 0.2649 0.3535 0.028 Uiso 1 1 calc R U . . .
C16 C 0.1318(3) 0.2587(3) 0.4469(2) 0.0202(10) Uani 1 1 d . . . . .
Cu2 Cu 0.23487(3) 0.19535(3) -0.04330(2) 0.01949(15) Uani 1 1 d . . . . .
O15 O 0.27829(17) 0.28084(18) 0.02179(13) 0.0220(7) Uani 1 1 d . . . . .
O16 O 0.12364(18) 0.29652(19) -0.05157(14) 0.0261(7) Uani 1 1 d . . . . .
O17 O 0.0225(2) 0.2847(3) -0.00609(16) 0.0491(10) Uani 1 1 d . . . . .
O18 O 0.0492(2) 0.3423(2) 0.20332(16) 0.0432(9) Uani 1 1 d . . . . .
O19 O 0.1688(2) 0.3617(2) 0.26599(15) 0.0419(9) Uani 1 1 d . . . . .
O21 O 0.41045(19) 0.3598(2) 0.09879(14) 0.0321(8) Uani 1 1 d . . . . .
O22 O 0.4128(2) 0.2908(3) 0.18389(17) 0.0606(12) Uani 1 1 d . . . . .
O23 O 0.18392(18) 0.12774(18) 0.01299(13) 0.0222(7) Uani 1 1 d . . . . .
O24 O 0.34212(19) 0.1018(2) 0.00419(14) 0.0316(8) Uani 1 1 d . . . . .
O25 O 0.4372(2) 0.1073(3) 0.08831(16) 0.0545(11) Uani 1 1 d . . . . .
O26 O 0.3837(2) 0.0533(2) 0.28420(14) 0.0415(9) Uani 1 1 d . . . . .
O27 O 0.2577(2) 0.0580(2) 0.29698(15) 0.0433(9) Uani 1 1 d . . . . .
O28 O 0.0331(2) 0.1378(2) 0.12303(15) 0.0375(9) Uani 1 1 d . . . . .
O29 O 0.0428(2) 0.0691(3) 0.03962(15) 0.0480(10) Uani 1 1 d . . . . .
N17 N 0.3365(2) 0.3636(2) -0.14844(15) 0.0199(8) Uani 1 1 d . . . . .
N18 N 0.2563(2) 0.3614(2) -0.17995(16) 0.0271(9) Uani 1 1 d . . . . .
N19 N 0.2201(2) 0.3049(2) -0.15158(16) 0.0240(9) Uani 1 1 d . . . . .
N20 N 0.2756(2) 0.2708(2) -0.10230(15) 0.0211(8) Uani 1 1 d . . . . .
N21 N 0.3966(3) 0.4176(3) -0.1652(2) 0.0286(10) Uani 1 1 d . . . . .
N22 N 0.1298(2) 0.0109(2) -0.17105(15) 0.0193(8) Uani 1 1 d . . . . .
N23 N 0.2089(2) 0.0086(2) -0.17692(16) 0.0234(9) Uani 1 1 d . . . . .
N24 N 0.2479(2) 0.0672(2) -0.13908(17) 0.0262(9) Uani 1 1 d . . . . .
N25 N 0.1943(2) 0.1073(2) -0.10881(15) 0.0191(8) Uani 1 1 d . . . . .
N26 N 0.0717(3) -0.0449(3) -0.2085(2) 0.0278(10) Uani 1 1 d . . . . .
N27 N 0.0961(2) 0.2965(2) -0.00389(18) 0.0272(9) Uani 1 1 d . . . . .
N28 N 0.1251(3) 0.3477(2) 0.21427(19) 0.0326(10) Uani 1 1 d . . . . .
N29 N 0.3763(2) 0.3261(2) 0.13628(17) 0.0263(9) Uani 1 1 d . . . . .
N30 N 0.3647(3) 0.1034(2) 0.06126(19) 0.0297(10) Uani 1 1 d . . . . .
N31 N 0.3087(3) 0.0622(3) 0.26418(18) 0.0338(10) Uani 1 1 d . . . . .
N32 N 0.0736(2) 0.1029(3) 0.08964(18) 0.0297(10) Uani 1 1 d . . . . .
C17 C 0.3487(3) 0.3075(3) -0.10038(19) 0.0185(10) Uani 1 1 d . . . . .
C18 C 0.4270(3) 0.2900(3) -0.0554(2) 0.0286(11) Uani 1 1 d . . . . .
H18A H 0.4189 0.2973 -0.0134 0.043 Uiso 1 1 calc R U . . .
H18B H 0.4694 0.3318 -0.0621 0.043 Uiso 1 1 calc R U . . .
H18C H 0.4452 0.2293 -0.0608 0.043 Uiso 1 1 calc R U . . .
C19 C 0.1212(3) 0.0708(3) -0.12865(18) 0.0189(10) Uani 1 1 d . . . . .
C20 C 0.0433(3) 0.0913(3) -0.1107(2) 0.0297(11) Uani 1 1 d . . . . .
H20A H 0.0371 0.0520 -0.0769 0.044 Uiso 1 1 calc R U . . .
H20B H -0.0035 0.0825 -0.1462 0.044 Uiso 1 1 calc R U . . .
H20C H 0.0442 0.1530 -0.0969 0.044 Uiso 1 1 calc R U . . .
C21 C 0.2401(3) 0.3066(3) 0.06259(19) 0.0172(9) Uani 1 1 d . . . . .
C22 C 0.1527(3) 0.3108(3) 0.05571(19) 0.0195(10) Uani 1 1 d . . . . .
C23 C 0.1163(3) 0.3263(3) 0.1049(2) 0.0247(11) Uani 1 1 d . . . . .
H23 H 0.0577 0.3287 0.0985 0.030 Uiso 1 1 calc R U . . .
C24 C 0.1656(3) 0.3382(3) 0.1627(2) 0.0229(10) Uani 1 1 d . . . . .
C25 C 0.2510(3) 0.3405(3) 0.1732(2) 0.0245(11) Uani 1 1 d . . . . .
H25 H 0.2845 0.3511 0.2134 0.029 Uiso 1 1 calc R U . . .
C26 C 0.2857(3) 0.3271(3) 0.1238(2) 0.0192(10) Uani 1 1 d . . . . .
C27 C 0.2160(3) 0.1076(3) 0.0697(2) 0.0203(10) Uani 1 1 d . . . . .
C28 C 0.3015(3) 0.0986(3) 0.0983(2) 0.0216(10) Uani 1 1 d . . . . .
C29 C 0.3319(3) 0.0848(3) 0.1610(2) 0.0258(11) Uani 1 1 d . . . . .
H29 H 0.3898 0.0796 0.1778 0.031 Uiso 1 1 calc R U . . .
C30 C 0.2769(3) 0.0786(3) 0.1985(2) 0.0236(11) Uani 1 1 d . . . . .
C31 C 0.1928(3) 0.0853(3) 0.1746(2) 0.0249(11) Uani 1 1 d . . . . .
H31 H 0.1554 0.0812 0.2012 0.030 Uiso 1 1 calc R U . . .
C32 C 0.1632(3) 0.0979(3) 0.1122(2) 0.0218(10) Uani 1 1 d . . . . .
O30 O 0.0607(3) 0.5545(3) 0.58475(19) 0.0809(15) Uani 1 1 d . . . . .
H30A H 0.0236 0.5394 0.5512 0.097 Uiso 1 1 d R U . . .
H30B H 0.1012 0.5453 0.5844 0.097 Uiso 1 1 d R U . . .
O10 O 0.1144(4) -0.0263(3) 0.52153(18) 0.123(2) Uani 1 1 d . . . . .
O6A O 0.4133(5) 0.0094(5) 0.4652(6) 0.057(4) Uani 0.497(13) 1 d . . P A 1
O7A O 0.3046(7) 0.0051(5) 0.5015(4) 0.036(3) Uani 0.503(13) 1 d . . P A 1
O6B O 0.4068(6) 0.0166(5) 0.5211(5) 0.068(4) Uani 0.503(13) 1 d . . P A 2
O7B O 0.2956(8) 0.0024(7) 0.4543(11) 0.125(7) Uani 0.497(13) 1 d . . P A 2
H5B H 0.547(3) 0.083(3) 0.803(2) 0.040(16) Uiso 1 1 d . . . . .
H26B H 0.033(3) -0.008(3) -0.225(2) 0.029(15) Uiso 1 1 d . . . . .
H5A H 0.491(2) 0.054(3) 0.8395(19) 0.013(13) Uiso 1 1 d . . . . .
H21A H 0.388(3) 0.409(3) -0.203(2) 0.036(16) Uiso 1 1 d . . . . .
H21B H 0.378(3) 0.467(4) -0.157(2) 0.06(2) Uiso 1 1 d . . . . .
H26A H 0.049(3) -0.079(4) -0.188(2) 0.06(2) Uiso 1 1 d . . . . .
H10B H 0.071(3) 0.302(3) 0.805(2) 0.023(13) Uiso 1 1 d . . . . .
H10A H -0.003(3) 0.277(3) 0.766(2) 0.047(18) Uiso 1 1 d . . . . .


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 O8 1.946(3) . ?
Cu1 O1 1.960(3) . ?
Cu1 N4 1.972(4) . ?
Cu1 N9 1.996(4) . ?
Cu1 O9 2.346(3) . ?
O1 C5 1.281(5) . ?
O2 N11 1.238(4) . ?
O3 N11 1.218(4) . ?
O4 N12 1.220(5) . ?
O5 N12 1.235(5) . ?
O8 C11 1.272(5) . ?
O9 N14 1.215(5) . ?
O11 N15 1.230(4) . ?
O12 N15 1.231(4) . ?
O13 N16 1.228(4) . ?
O14 N16 1.225(5) . ?
N1 C1 1.337(5) . ?
N1 N2 1.353(5) . ?
N1 N5 1.389(5) . ?
N2 N3 1.288(5) . ?
N3 N4 1.367(5) . ?
N4 C1 1.317(5) . ?
N6 C3 1.340(5) . ?
N6 N7 1.351(5) . ?
N6 N10 1.401(5) . ?
N7 N8 1.284(5) . ?
N8 N9 1.368(5) . ?
N9 C3 1.317(5) . ?
N11 C6 1.457(5) . ?
N12 C8 1.449(5) . ?
N13 O7A 1.168(9) . ?
N13 O6B 1.175(9) . ?
N13 O7B 1.200(12) . ?
N13 O6A 1.267(8) . ?
N13 C10 1.458(6) . ?
N14 O10 1.218(5) . ?
N14 C12 1.457(5) . ?
N15 C14 1.460(5) . ?
N16 C16 1.461(5) . ?
C1 C2 1.478(6) . ?
C3 C4 1.460(6) . ?
C5 C6 1.421(6) . ?
C5 C10 1.439(6) . ?
C6 C7 1.382(6) . ?
C7 C8 1.364(6) . ?
C8 C9 1.383(6) . ?
C9 C10 1.361(6) . ?
C11 C12 1.427(6) . ?
C11 C16 1.442(6) . ?
C12 C13 1.378(6) . ?
C13 C14 1.371(6) . ?
C14 C15 1.370(6) . ?
C15 C16 1.369(6) . ?
Cu2 O15 1.948(3) . ?
Cu2 O23 1.950(3) . ?
Cu2 N20 1.969(3) . ?
Cu2 N25 1.971(3) . ?
Cu2 O24 2.324(3) . ?
Cu2 O16 2.368(3) . ?
O15 C21 1.279(5) . ?
O16 N27 1.246(4) . ?
O17 N27 1.222(4) . ?
O18 N28 1.228(5) . ?
O19 N28 1.228(5) . ?
O21 N29 1.220(4) . ?
O22 N29 1.214(5) . ?
O23 C27 1.286(5) . ?
O24 N30 1.237(4) . ?
O25 N30 1.215(5) . ?
O26 N31 1.228(5) . ?
O27 N31 1.237(5) . ?
O28 N32 1.227(4) . ?
O29 N32 1.223(4) . ?
N17 C17 1.341(5) . ?
N17 N18 1.353(5) . ?
N17 N21 1.401(5) . ?
N18 N19 1.287(5) . ?
N19 N20 1.359(5) . ?
N20 C17 1.323(5) . ?
N22 C19 1.337(5) . ?
N22 N23 1.348(4) . ?
N22 N26 1.401(5) . ?
N23 N24 1.288(5) . ?
N24 N25 1.372(4) . ?
N25 C19 1.312(5) . ?
N27 C22 1.452(5) . ?
N28 C24 1.461(5) . ?
N29 C26 1.463(5) . ?
N30 C28 1.474(5) . ?
N31 C30 1.454(5) . ?
N32 C32 1.456(6) . ?
C17 C18 1.469(6) . ?
C19 C20 1.469(6) . ?
C21 C22 1.423(6) . ?
C21 C26 1.430(6) . ?
C22 C23 1.384(6) . ?
C23 C24 1.366(6) . ?
C24 C25 1.382(6) . ?
C25 C26 1.365(6) . ?
C27 C28 1.421(6) . ?
C27 C32 1.435(6) . ?
C28 C29 1.383(6) . ?
C29 C30 1.372(6) . ?
C30 C31 1.377(6) . ?
C31 C32 1.374(6) . ?

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
O8 Cu1 O1 91.58(12) . . ?
O8 Cu1 N4 171.54(14) . . ?
O1 Cu1 N4 90.30(14) . . ?
O8 Cu1 N9 89.56(13) . . ?
O1 Cu1 N9 171.18(14) . . ?
N4 Cu1 N9 89.85(15) . . ?
O8 Cu1 O9 79.32(11) . . ?
O1 Cu1 O9 86.05(12) . . ?
N4 Cu1 O9 109.05(13) . . ?
N9 Cu1 O9 85.58(13) . . ?
C5 O1 Cu1 126.6(3) . . ?
C11 O8 Cu1 127.7(3) . . ?
N14 O9 Cu1 125.2(3) . . ?
C1 N1 N2 109.6(4) . . ?
C1 N1 N5 126.1(4) . . ?
N2 N1 N5 124.2(4) . . ?
N3 N2 N1 106.3(3) . . ?
N2 N3 N4 109.8(4) . . ?
C1 N4 N3 107.4(4) . . ?
C1 N4 Cu1 133.1(3) . . ?
N3 N4 Cu1 119.5(3) . . ?
C3 N6 N7 110.5(3) . . ?
C3 N6 N10 126.1(4) . . ?
N7 N6 N10 123.3(3) . . ?
N8 N7 N6 105.9(3) . . ?
N7 N8 N9 109.7(4) . . ?
C3 N9 N8 108.1(4) . . ?
C3 N9 Cu1 133.2(3) . . ?
N8 N9 Cu1 118.5(3) . . ?
O3 N11 O2 122.7(4) . . ?
O3 N11 C6 118.3(4) . . ?
O2 N11 C6 119.0(4) . . ?
O4 N12 O5 123.0(4) . . ?
O4 N12 C8 119.4(4) . . ?
O5 N12 C8 117.6(4) . . ?
O6B N13 O7B 123.7(9) . . ?
O7A N13 O6A 122.6(6) . . ?
O7A N13 C10 122.1(6) . . ?
O6B N13 C10 118.8(6) . . ?
O7B N13 C10 116.6(7) . . ?
O6A N13 C10 115.2(5) . . ?
O9 N14 O10 120.3(4) . . ?
O9 N14 C12 122.5(4) . . ?
O10 N14 C12 117.1(4) . . ?
O11 N15 O12 123.5(4) . . ?
O11 N15 C14 118.5(4) . . ?
O12 N15 C14 118.0(4) . . ?
O14 N16 O13 123.5(4) . . ?
O14 N16 C16 118.3(4) . . ?
O13 N16 C16 118.1(4) . . ?
N4 C1 N1 106.9(4) . . ?
N4 C1 C2 128.4(4) . . ?
N1 C1 C2 124.7(4) . . ?
N9 C3 N6 105.7(4) . . ?
N9 C3 C4 127.9(4) . . ?
N6 C3 C4 126.4(4) . . ?
O1 C5 C6 127.7(4) . . ?
O1 C5 C10 119.3(4) . . ?
C6 C5 C10 113.0(4) . . ?
C7 C6 C5 123.0(4) . . ?
C7 C6 N11 116.0(4) . . ?
C5 C6 N11 121.0(4) . . ?
C8 C7 C6 119.9(4) . . ?
C7 C8 C9 121.2(4) . . ?
C7 C8 N12 118.9(4) . . ?
C9 C8 N12 119.9(4) . . ?
C10 C9 C8 118.6(4) . . ?
C9 C10 C5 124.3(4) . . ?
C9 C10 N13 117.9(4) . . ?
C5 C10 N13 117.8(4) . . ?
O8 C11 C12 126.8(4) . . ?
O8 C11 C16 120.8(4) . . ?
C12 C11 C16 112.3(4) . . ?
C13 C12 C11 124.2(4) . . ?
C13 C12 N14 115.1(4) . . ?
C11 C12 N14 120.7(4) . . ?
C14 C13 C12 118.6(4) . . ?
C15 C14 C13 121.9(4) . . ?
C15 C14 N15 119.4(4) . . ?
C13 C14 N15 118.5(4) . . ?
C16 C15 C14 118.9(4) . . ?
C15 C16 C11 123.9(4) . . ?
C15 C16 N16 117.1(4) . . ?
C11 C16 N16 119.0(4) . . ?
O15 Cu2 O23 90.65(11) . . ?
O15 Cu2 N20 89.20(13) . . ?
O23 Cu2 N20 174.05(14) . . ?
O15 Cu2 N25 178.28(14) . . ?
O23 Cu2 N25 89.76(13) . . ?
N20 Cu2 N25 90.56(14) . . ?
O15 Cu2 O24 87.23(12) . . ?
O23 Cu2 O24 77.88(11) . . ?
N20 Cu2 O24 108.05(13) . . ?
N25 Cu2 O24 91.22(13) . . ?
O15 Cu2 O16 77.23(11) . . ?
O23 Cu2 O16 86.73(11) . . ?
N20 Cu2 O16 87.44(13) . . ?
N25 Cu2 O16 104.46(13) . . ?
O24 Cu2 O16 158.01(11) . . ?
C21 O15 Cu2 124.6(3) . . ?
N27 O16 Cu2 111.4(2) . . ?
C27 O23 Cu2 127.5(3) . . ?
N30 O24 Cu2 118.2(3) . . ?
C17 N17 N18 110.3(3) . . ?
C17 N17 N21 126.4(4) . . ?
N18 N17 N21 123.4(3) . . ?
N19 N18 N17 106.0(3) . . ?
N18 N19 N20 109.9(4) . . ?
C17 N20 N19 108.2(3) . . ?
C17 N20 Cu2 132.2(3) . . ?
N19 N20 Cu2 118.9(3) . . ?
C19 N22 N23 110.5(3) . . ?
C19 N22 N26 130.9(4) . . ?
N23 N22 N26 118.6(3) . . ?
N24 N23 N22 105.8(3) . . ?
N23 N24 N25 109.8(3) . . ?
C19 N25 N24 107.6(3) . . ?
C19 N25 Cu2 131.5(3) . . ?
N24 N25 Cu2 120.6(3) . . ?
O17 N27 O16 121.6(4) . . ?
O17 N27 C22 119.3(4) . . ?
O16 N27 C22 119.2(4) . . ?
O19 N28 O18 123.7(4) . . ?
O19 N28 C24 118.1(4) . . ?
O18 N28 C24 118.2(4) . . ?
O22 N29 O21 124.1(4) . . ?
O22 N29 C26 117.0(4) . . ?
O21 N29 C26 118.9(4) . . ?
O25 N30 O24 122.7(4) . . ?
O25 N30 C28 118.3(4) . . ?
O24 N30 C28 119.0(4) . . ?
O26 N31 O27 123.6(4) . . ?
O26 N31 C30 119.0(4) . . ?
O27 N31 C30 117.4(4) . . ?
O29 N32 O28 123.9(4) . . ?
O29 N32 C32 118.0(4) . . ?
O28 N32 C32 118.0(4) . . ?
N20 C17 N17 105.6(4) . . ?
N20 C17 C18 127.4(4) . . ?
N17 C17 C18 127.0(4) . . ?
N25 C19 N22 106.3(4) . . ?
N25 C19 C20 128.5(4) . . ?
N22 C19 C20 125.2(4) . . ?
O15 C21 C22 126.5(4) . . ?
O15 C21 C26 120.1(4) . . ?
C22 C21 C26 113.2(4) . . ?
C23 C22 C21 122.7(4) . . ?
C23 C22 N27 115.9(4) . . ?
C21 C22 N27 121.4(4) . . ?
C24 C23 C22 119.3(4) . . ?
C23 C24 C25 122.0(4) . . ?
C23 C24 N28 117.8(4) . . ?
C25 C24 N28 120.2(4) . . ?
C26 C25 C24 117.7(4) . . ?
C25 C26 C21 124.7(4) . . ?
C25 C26 N29 116.9(4) . . ?
C21 C26 N29 118.1(4) . . ?
O23 C27 C28 127.3(4) . . ?
O23 C27 C32 119.4(4) . . ?
C28 C27 C32 113.1(4) . . ?
C29 C28 C27 124.0(4) . . ?
C29 C28 N30 115.4(4) . . ?
C27 C28 N30 120.6(4) . . ?
C30 C29 C28 118.9(5) . . ?
C29 C30 C31 121.1(4) . . ?
C29 C30 N31 118.9(4) . . ?
C31 C30 N31 120.0(4) . . ?
C32 C31 C30 119.6(4) . . ?
C31 C32 C27 123.2(4) . . ?
C31 C32 N32 117.0(4) . . ?
C27 C32 N32 119.8(4) . . ?

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 N1 N2 N3 0.3(5) . . . . ?
N5 N1 N2 N3 178.7(4) . . . . ?
N1 N2 N3 N4 -0.1(5) . . . . ?
N2 N3 N4 C1 -0.2(5) . . . . ?
N2 N3 N4 Cu1 -178.4(3) . . . . ?
C3 N6 N7 N8 0.1(5) . . . . ?
N10 N6 N7 N8 -176.5(4) . . . . ?
N6 N7 N8 N9 0.6(5) . . . . ?
N7 N8 N9 C3 -1.0(5) . . . . ?
N7 N8 N9 Cu1 174.7(3) . . . . ?
Cu1 O9 N14 O10 172.0(5) . . . . ?
Cu1 O9 N14 C12 -11.1(7) . . . . ?
N3 N4 C1 N1 0.4(5) . . . . ?
Cu1 N4 C1 N1 178.3(3) . . . . ?
N3 N4 C1 C2 -178.3(4) . . . . ?
Cu1 N4 C1 C2 -0.4(7) . . . . ?
N2 N1 C1 N4 -0.4(5) . . . . ?
N5 N1 C1 N4 -178.7(4) . . . . ?
N2 N1 C1 C2 178.3(4) . . . . ?
N5 N1 C1 C2 0.0(7) . . . . ?
N8 N9 C3 N6 1.1(5) . . . . ?
Cu1 N9 C3 N6 -173.8(3) . . . . ?
N8 N9 C3 C4 -178.9(4) . . . . ?
Cu1 N9 C3 C4 6.3(7) . . . . ?
N7 N6 C3 N9 -0.8(5) . . . . ?
N10 N6 C3 N9 175.8(4) . . . . ?
N7 N6 C3 C4 179.2(4) . . . . ?
N10 N6 C3 C4 -4.2(7) . . . . ?
Cu1 O1 C5 C6 36.9(6) . . . . ?
Cu1 O1 C5 C10 -141.5(3) . . . . ?
O1 C5 C6 C7 -175.9(4) . . . . ?
C10 C5 C6 C7 2.5(6) . . . . ?
O1 C5 C6 N11 4.4(7) . . . . ?
C10 C5 C6 N11 -177.2(4) . . . . ?
O3 N11 C6 C7 8.8(6) . . . . ?
O2 N11 C6 C7 -171.1(4) . . . . ?
O3 N11 C6 C5 -171.5(4) . . . . ?
O2 N11 C6 C5 8.6(6) . . . . ?
C5 C6 C7 C8 -0.1(7) . . . . ?
N11 C6 C7 C8 179.6(4) . . . . ?
C6 C7 C8 C9 -2.2(7) . . . . ?
C6 C7 C8 N12 179.4(4) . . . . ?
O4 N12 C8 C7 -2.5(6) . . . . ?
O5 N12 C8 C7 177.3(4) . . . . ?
O4 N12 C8 C9 179.1(4) . . . . ?
O5 N12 C8 C9 -1.1(6) . . . . ?
C7 C8 C9 C10 1.8(7) . . . . ?
N12 C8 C9 C10 -179.8(4) . . . . ?
C8 C9 C10 C5 0.9(7) . . . . ?
C8 C9 C10 N13 -179.5(4) . . . . ?
O1 C5 C10 C9 175.7(4) . . . . ?
C6 C5 C10 C9 -2.9(6) . . . . ?
O1 C5 C10 N13 -4.0(6) . . . . ?
C6 C5 C10 N13 177.4(4) . . . . ?
O7A N13 C10 C9 -129.6(8) . . . . ?
O6B N13 C10 C9 120.1(9) . . . . ?
O7B N13 C10 C9 -70.3(15) . . . . ?
O6A N13 C10 C9 48.7(8) . . . . ?
O7A N13 C10 C5 50.1(9) . . . . ?
O6B N13 C10 C5 -60.2(9) . . . . ?
O7B N13 C10 C5 109.4(14) . . . . ?
O6A N13 C10 C5 -131.6(7) . . . . ?
Cu1 O8 C11 C12 34.8(6) . . . . ?
Cu1 O8 C11 C16 -142.6(3) . . . . ?
O8 C11 C12 C13 -175.0(4) . . . . ?
C16 C11 C12 C13 2.6(6) . . . . ?
O8 C11 C12 N14 8.1(7) . . . . ?
C16 C11 C12 N14 -174.3(4) . . . . ?
O9 N14 C12 C13 166.4(5) . . . . ?
O10 N14 C12 C13 -16.7(7) . . . . ?
O9 N14 C12 C11 -16.5(7) . . . . ?
O10 N14 C12 C11 160.5(5) . . . . ?
C11 C12 C13 C14 1.1(7) . . . . ?
N14 C12 C13 C14 178.2(4) . . . . ?
C12 C13 C14 C15 -2.9(7) . . . . ?
C12 C13 C14 N15 -179.1(4) . . . . ?
O11 N15 C14 C15 -179.1(4) . . . . ?
O12 N15 C14 C15 0.4(6) . . . . ?
O11 N15 C14 C13 -2.8(6) . . . . ?
O12 N15 C14 C13 176.7(4) . . . . ?
C13 C14 C15 C16 0.5(6) . . . . ?
N15 C14 C15 C16 176.7(4) . . . . ?
C14 C15 C16 C11 3.7(6) . . . . ?
C14 C15 C16 N16 -176.1(4) . . . . ?
O8 C11 C16 C15 172.7(4) . . . . ?
C12 C11 C16 C15 -5.1(6) . . . . ?
O8 C11 C16 N16 -7.5(6) . . . . ?
C12 C11 C16 N16 174.7(4) . . . . ?
O14 N16 C16 C15 147.8(4) . . . . ?
O13 N16 C16 C15 -29.6(6) . . . . ?
O14 N16 C16 C11 -32.0(6) . . . . ?
O13 N16 C16 C11 150.5(4) . . . . ?
C17 N17 N18 N19 0.0(4) . . . . ?
N21 N17 N18 N19 180.0(4) . . . . ?
N17 N18 N19 N20 0.1(4) . . . . ?
N18 N19 N20 C17 -0.2(5) . . . . ?
N18 N19 N20 Cu2 171.4(3) . . . . ?
C19 N22 N23 N24 -0.8(5) . . . . ?
N26 N22 N23 N24 178.1(4) . . . . ?
N22 N23 N24 N25 0.1(4) . . . . ?
N23 N24 N25 C19 0.7(5) . . . . ?
N23 N24 N25 Cu2 176.0(3) . . . . ?
Cu2 O16 N27 O17 -126.3(4) . . . . ?
Cu2 O16 N27 C22 53.6(4) . . . . ?
Cu2 O24 N30 O25 -133.1(4) . . . . ?
Cu2 O24 N30 C28 48.3(5) . . . . ?
N19 N20 C17 N17 0.2(4) . . . . ?
Cu2 N20 C17 N17 -169.9(3) . . . . ?
N19 N20 C17 C18 -179.3(4) . . . . ?
Cu2 N20 C17 C18 10.6(7) . . . . ?
N18 N17 C17 N20 -0.1(4) . . . . ?
N21 N17 C17 N20 179.9(4) . . . . ?
N18 N17 C17 C18 179.4(4) . . . . ?
N21 N17 C17 C18 -0.5(7) . . . . ?
N24 N25 C19 N22 -1.1(4) . . . . ?
Cu2 N25 C19 N22 -175.8(3) . . . . ?
N24 N25 C19 C20 -179.5(4) . . . . ?
Cu2 N25 C19 C20 5.9(7) . . . . ?
N23 N22 C19 N25 1.2(5) . . . . ?
N26 N22 C19 N25 -177.5(4) . . . . ?
N23 N22 C19 C20 179.6(4) . . . . ?
N26 N22 C19 C20 0.9(7) . . . . ?
Cu2 O15 C21 C22 -28.5(6) . . . . ?
Cu2 O15 C21 C26 145.8(3) . . . . ?
O15 C21 C22 C23 169.8(4) . . . . ?
C26 C21 C22 C23 -4.9(6) . . . . ?
O15 C21 C22 N27 -8.6(6) . . . . ?
C26 C21 C22 N27 176.8(4) . . . . ?
O17 N27 C22 C23 -11.6(6) . . . . ?
O16 N27 C22 C23 168.4(4) . . . . ?
O17 N27 C22 C21 166.8(4) . . . . ?
O16 N27 C22 C21 -13.1(6) . . . . ?
C21 C22 C23 C24 0.0(6) . . . . ?
N27 C22 C23 C24 178.4(4) . . . . ?
C22 C23 C24 C25 4.0(7) . . . . ?
C22 C23 C24 N28 -175.5(4) . . . . ?
O19 N28 C24 C23 -177.4(4) . . . . ?
O18 N28 C24 C23 1.9(6) . . . . ?
O19 N28 C24 C25 3.2(6) . . . . ?
O18 N28 C24 C25 -177.6(4) . . . . ?
C23 C24 C25 C26 -2.5(6) . . . . ?
N28 C24 C25 C26 177.0(4) . . . . ?
C24 C25 C26 C21 -3.2(6) . . . . ?
C24 C25 C26 N29 -177.5(4) . . . . ?
O15 C21 C26 C25 -168.4(4) . . . . ?
C22 C21 C26 C25 6.6(6) . . . . ?
O15 C21 C26 N29 5.8(6) . . . . ?
C22 C21 C26 N29 -179.2(3) . . . . ?
O22 N29 C26 C25 38.4(6) . . . . ?
O21 N29 C26 C25 -141.9(4) . . . . ?
O22 N29 C26 C21 -136.3(4) . . . . ?
O21 N29 C26 C21 43.4(5) . . . . ?
Cu2 O23 C27 C28 -25.9(6) . . . . ?
Cu2 O23 C27 C32 149.5(3) . . . . ?
O23 C27 C28 C29 173.7(4) . . . . ?
C32 C27 C28 C29 -1.9(6) . . . . ?
O23 C27 C28 N30 -6.5(6) . . . . ?
C32 C27 C28 N30 177.8(4) . . . . ?
O25 N30 C28 C29 -9.9(6) . . . . ?
O24 N30 C28 C29 168.9(4) . . . . ?
O25 N30 C28 C27 170.4(4) . . . . ?
O24 N30 C28 C27 -10.9(6) . . . . ?
C27 C28 C29 C30 0.4(6) . . . . ?
N30 C28 C29 C30 -179.3(4) . . . . ?
C28 C29 C30 C31 0.5(6) . . . . ?
C28 C29 C30 N31 178.7(4) . . . . ?
O26 N31 C30 C29 -0.8(6) . . . . ?
O27 N31 C30 C29 179.1(4) . . . . ?
O26 N31 C30 C31 177.5(4) . . . . ?
O27 N31 C30 C31 -2.6(6) . . . . ?
C29 C30 C31 C32 0.3(6) . . . . ?
N31 C30 C31 C32 -177.9(4) . . . . ?
C30 C31 C32 C27 -2.1(7) . . . . ?
C30 C31 C32 N32 179.0(4) . . . . ?
O23 C27 C32 C31 -173.3(4) . . . . ?
C28 C27 C32 C31 2.8(6) . . . . ?
O23 C27 C32 N32 5.6(6) . . . . ?
C28 C27 C32 N32 -178.3(4) . . . . ?
O29 N32 C32 C31 -142.4(4) . . . . ?
O28 N32 C32 C31 34.8(6) . . . . ?
O29 N32 C32 C27 38.6(6) . . . . ?
O28 N32 C32 C27 -144.2(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
C2 H2B N10 0.98 2.61 3.508(6) 153.0 2_546
C4 H4A N23 0.98 2.54 3.346(6) 139.2 2
C9 H9 O27 0.95 2.56 3.291(6) 133.5 .
C13 H13 O21 0.95 2.42 3.366(5) 177.5 2_545
C18 H18A O15 0.98 2.63 3.314(5) 126.7 .
C20 H20A O29 0.98 2.58 3.356(6) 136.1 .
C20 H20A O29 0.98 2.51 3.379(6) 148.2 3
C20 H20B O4 0.98 2.49 3.205(6) 129.4 4_565
C20 H20C O16 0.98 2.61 3.505(5) 151.5 .
C31 H31 O12 0.95 2.53 3.388(5) 150.3 .
N5 H5B O18 0.91(5) 2.49(5) 3.007(6) 117(4) 4_666
N5 H5B O19 0.91(5) 2.49(5) 3.383(6) 166(4) 4_666
N26 H26B O11 0.87(5) 2.37(5) 3.019(5) 132(4) 3
N5 H5A O30 0.78(4) 2.06(4) 2.813(6) 163(4) 2_546
N21 H21A N26 0.83(5) 2.32(5) 3.024(6) 142(4) 2_554
N21 H21B O9 0.84(5) 2.38(5) 3.147(6) 152(5) 2
N26 H26A O28 0.83(5) 2.37(5) 3.179(6) 163(5) 3
N10 H10B N19 0.88(4) 2.44(4) 3.086(6) 131(3) 1_556
N10 H10A O22 0.86(5) 2.26(5) 2.862(6) 127(4) 4_566
C2 H2B N10 0.98 2.61 3.508(6) 153.0 2_546
C4 H4A N23 0.98 2.54 3.346(6) 139.2 2
C9 H9 O27 0.95 2.56 3.291(6) 133.5 .
C13 H13 O21 0.95 2.42 3.366(5) 177.5 2_545
C18 H18A O15 0.98 2.63 3.314(5) 126.7 .
C20 H20A O29 0.98 2.58 3.356(6) 136.1 .
C20 H20A O29 0.98 2.51 3.379(6) 148.2 3
C20 H20B O4 0.98 2.49 3.205(6) 129.4 4_565
C20 H20C O16 0.98 2.61 3.505(5) 151.5 .
C31 H31 O12 0.95 2.53 3.388(5) 150.3 .
N5 H5B O18 0.91(5) 2.49(5) 3.007(6) 117(4) 4_666
N5 H5B O19 0.91(5) 2.49(5) 3.383(6) 166(4) 4_666
N26 H26B O11 0.87(5) 2.37(5) 3.019(5) 132(4) 3
N5 H5A O30 0.78(4) 2.06(4) 2.813(6) 163(4) 2_546
N21 H21A N26 0.83(5) 2.32(5) 3.024(6) 142(4) 2_554
N21 H21B O9 0.84(5) 2.38(5) 3.147(6) 152(5) 2
N26 H26A O28 0.83(5) 2.37(5) 3.179(6) 163(5) 3
N10 H10B N19 0.88(4) 2.44(4) 3.086(6) 131(3) 1_556
N10 H10A O22 0.86(5) 2.26(5) 2.862(6) 127(4) 4_566

_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.
;



_refine_diff_density_max         0.725
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.097

_shelxl_version_number           2013-4


####################################################################### 
# 
# 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_mx190
_database_code_depnum_ccdc_archive 'CCDC 1934809'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             
;
'Tue Apr 25 21:57:08 2017'
;
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
bis(2-aminotetrazolyl) copper(II) bis(picrate)
;
_chemical_name_common            
'bis(2-aminotetrazolyl) copper(II) bis(picrate)'
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Cu N16 O14'
_chemical_formula_sum            'C14 H10 Cu N16 O14'
_chemical_formula_weight         689.92

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_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                   13.0030(8)
_cell_length_b                   13.5703(11)
_cell_length_c                   6.8287(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.619(6)
_cell_angle_gamma                90
_cell_volume                     1202.55(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1403
_cell_measurement_theta_min      4.4350
_cell_measurement_theta_max      30.9710

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.017
_shelx_estimated_absorpt_T_min   0.605
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70027
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_F_000             694
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            9343
_diffrn_reflns_av_unetI/netI     0.0853
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_sigmaI/netI    0.1883
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.238
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2359
_reflns_number_gt                1648
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;

_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'enCIFer 1.5.1 (CCDC 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0118P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2359
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      -0.0275080000
_diffrn_orient_matrix_UB_12      -0.0390845000
_diffrn_orient_matrix_UB_13      0.0416593000
_diffrn_orient_matrix_UB_21      -0.0472211000
_diffrn_orient_matrix_UB_22      0.0223393000
_diffrn_orient_matrix_UB_23      -0.0333427000
_diffrn_orient_matrix_UB_31      0.0007284000
_diffrn_orient_matrix_UB_32      -0.0264943000
_diffrn_orient_matrix_UB_33      -0.0894494000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -29.00   -2.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.8557  -80.0000   88.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   72.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       29.9494  -99.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega  -62.00   42.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.8557   77.0000   90.0000 104

#__ type_ start__ end____ width___ exp.time_
  4 omega -100.00   -6.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.8557  -77.0000  -30.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega -100.00   13.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.8557  -19.0000  -30.0000 113

#__ type_ start__ end____ width___ exp.time_
  6 omega   42.00  110.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       29.9494  179.0000  -90.0000 68

;



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_
_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 0.0000 0.5000 0.5000 0.01941(18) Uani 1 2 d S . P . .
O1 O 0.06214(19) 0.62986(19) 0.3204(3) 0.0300(6) Uani 1 1 d . . . . .
O2 O 0.1715(2) 0.7117(2) 0.1708(4) 0.0533(9) Uani 1 1 d . . . . .
O3 O 0.13109(17) 0.52247(17) 0.6452(3) 0.0210(6) Uani 1 1 d . . . . .
O4 O 0.2239(2) 0.5048(2) 1.0049(4) 0.0440(8) Uani 1 1 d . . . . .
O5 O 0.3713(2) 0.4368(2) 0.9667(4) 0.0547(9) Uani 1 1 d . . . . .
O6 O 0.5920(2) 0.6243(2) 0.5549(4) 0.0355(7) Uani 1 1 d . . . . .
O7 O 0.5219(2) 0.7251(2) 0.3400(4) 0.0516(9) Uani 1 1 d . . . . .
N2 N 0.1671(2) 0.3116(2) 0.1991(4) 0.0238(7) Uani 1 1 d . . . . .
N1 N 0.0885(2) 0.3086(2) 0.0665(4) 0.0314(8) Uani 1 1 d . . . . .
C1 C 0.0246(3) 0.3711(3) 0.1441(5) 0.0278(9) Uani 1 1 d . . . . .
H1 H -0.0416 0.3870 0.0855 0.033 Uiso 1 1 calc R U . . .
N4 N 0.0627(2) 0.4095(2) 0.3134(4) 0.0209(7) Uani 1 1 d . . . . .
N5 N 0.2524(3) 0.2522(3) 0.1968(5) 0.0344(9) Uani 1 1 d . . . . .
N6 N 0.1506(2) 0.6551(2) 0.3017(4) 0.0249(7) Uani 1 1 d . . . . .
N7 N 0.2996(2) 0.4907(2) 0.9126(4) 0.0302(8) Uani 1 1 d . . . . .
N8 N 0.5163(3) 0.6612(2) 0.4666(5) 0.0316(8) Uani 1 1 d . . . . .
N3 N 0.1555(2) 0.3706(2) 0.3477(4) 0.0247(7) Uani 1 1 d . . . . .
C2 C 0.2347(3) 0.6204(2) 0.4338(5) 0.0182(8) Uani 1 1 d . . . . .
C3 C 0.2161(3) 0.5601(2) 0.6024(5) 0.0172(8) Uani 1 1 d . . . . .
C4 C 0.3085(3) 0.5442(2) 0.7259(5) 0.0207(8) Uani 1 1 d . . . . .
C5 C 0.4048(3) 0.5738(3) 0.6843(5) 0.0237(9) Uani 1 1 d . . . . .
C6 C 0.4148(3) 0.6283(3) 0.5140(5) 0.0238(8) Uani 1 1 d . . . . .
C7 C 0.3315(3) 0.6524(3) 0.3923(5) 0.0231(9) Uani 1 1 d . . . . .
H5 H 0.457(3) 0.559(3) 0.764(5) 0.025(10) Uiso 1 1 d . . . . .
H7 H 0.341(3) 0.687(3) 0.294(5) 0.037(12) Uiso 1 1 d . . . . .
H5A H 0.305(3) 0.284(3) 0.179(5) 0.027(12) Uiso 1 1 d . . . . .
H5B H 0.238(4) 0.205(4) 0.092(7) 0.090(19) Uiso 1 1 d . . . . .


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 O3 1.941(2) . ?
Cu1 O3 1.941(2) 3_566 ?
Cu1 N4 1.982(3) . ?
Cu1 N4 1.982(3) 3_566 ?
Cu1 O1 2.321(2) 3_566 ?
Cu1 O1 2.321(2) . ?
O1 N6 1.215(3) . ?
O2 N6 1.222(3) . ?
O3 C3 1.268(4) . ?
O4 N7 1.218(4) . ?
O5 N7 1.223(4) . ?
O6 N8 1.228(4) . ?
O7 N8 1.230(4) . ?
N2 N3 1.309(4) . ?
N2 N1 1.323(4) . ?
N2 N5 1.372(4) . ?
N1 C1 1.321(4) . ?
C1 N4 1.335(4) . ?
C1 H1 0.9500 . ?
N4 N3 1.325(4) . ?
N5 H5A 0.82(4) . ?
N5 H5B 0.97(5) . ?
N6 C2 1.451(4) . ?
N7 C4 1.477(4) . ?
N8 C6 1.449(4) . ?
C2 C7 1.377(5) . ?
C2 C3 1.445(4) . ?
C3 C4 1.440(5) . ?
C4 C5 1.363(5) . ?
C5 C6 1.391(5) . ?
C5 H5 0.87(4) . ?
C6 C7 1.363(5) . ?
C7 H7 0.83(3) . ?

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
O3 Cu1 O3 180.0 . 3_566 ?
O3 Cu1 N4 92.41(11) . . ?
O3 Cu1 N4 87.59(11) 3_566 . ?
O3 Cu1 N4 87.58(11) . 3_566 ?
O3 Cu1 N4 92.41(11) 3_566 3_566 ?
N4 Cu1 N4 180.0 . 3_566 ?
O3 Cu1 O1 99.97(9) . 3_566 ?
O3 Cu1 O1 80.03(9) 3_566 3_566 ?
N4 Cu1 O1 92.33(10) . 3_566 ?
N4 Cu1 O1 87.67(10) 3_566 3_566 ?
O3 Cu1 O1 80.03(9) . . ?
O3 Cu1 O1 99.97(9) 3_566 . ?
N4 Cu1 O1 87.67(10) . . ?
N4 Cu1 O1 92.33(10) 3_566 . ?
O1 Cu1 O1 180.0 3_566 . ?
N6 O1 Cu1 129.3(2) . . ?
C3 O3 Cu1 134.1(2) . . ?
N3 N2 N1 115.3(3) . . ?
N3 N2 N5 120.1(3) . . ?
N1 N2 N5 124.4(3) . . ?
C1 N1 N2 100.6(3) . . ?
N1 C1 N4 112.9(3) . . ?
N1 C1 H1 123.5 . . ?
N4 C1 H1 123.5 . . ?
N3 N4 C1 106.3(3) . . ?
N3 N4 Cu1 122.7(2) . . ?
C1 N4 Cu1 130.8(3) . . ?
N2 N5 H5A 112(3) . . ?
N2 N5 H5B 106(3) . . ?
H5A N5 H5B 111(4) . . ?
O1 N6 O2 120.6(3) . . ?
O1 N6 C2 121.6(3) . . ?
O2 N6 C2 117.8(3) . . ?
O4 N7 O5 124.3(3) . . ?
O4 N7 C4 118.6(3) . . ?
O5 N7 C4 117.1(3) . . ?
O6 N8 O7 123.4(3) . . ?
O6 N8 C6 118.5(3) . . ?
O7 N8 C6 118.0(3) . . ?
N2 N3 N4 104.8(3) . . ?
C7 C2 C3 123.0(3) . . ?
C7 C2 N6 115.6(3) . . ?
C3 C2 N6 121.4(3) . . ?
O3 C3 C4 120.8(3) . . ?
O3 C3 C2 127.2(3) . . ?
C4 C3 C2 112.1(3) . . ?
C5 C4 C3 125.3(3) . . ?
C5 C4 N7 116.6(3) . . ?
C3 C4 N7 118.2(3) . . ?
C4 C5 C6 117.8(4) . . ?
C4 C5 H5 120(2) . . ?
C6 C5 H5 123(2) . . ?
C7 C6 C5 121.7(3) . . ?
C7 C6 N8 119.3(3) . . ?
C5 C6 N8 119.0(3) . . ?
C6 C7 C2 120.0(3) . . ?
C6 C7 H7 118(3) . . ?
C2 C7 H7 122(3) . . ?

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
N3 N2 N1 C1 -0.2(4) . . . . ?
N5 N2 N1 C1 174.0(3) . . . . ?
N2 N1 C1 N4 0.1(4) . . . . ?
N1 C1 N4 N3 0.1(4) . . . . ?
N1 C1 N4 Cu1 -176.2(2) . . . . ?
Cu1 O1 N6 O2 164.6(3) . . . . ?
Cu1 O1 N6 C2 -16.1(4) . . . . ?
N1 N2 N3 N4 0.3(4) . . . . ?
N5 N2 N3 N4 -174.3(3) . . . . ?
C1 N4 N3 N2 -0.2(3) . . . . ?
Cu1 N4 N3 N2 176.5(2) . . . . ?
O1 N6 C2 C7 178.1(3) . . . . ?
O2 N6 C2 C7 -2.5(5) . . . . ?
O1 N6 C2 C3 -4.8(5) . . . . ?
O2 N6 C2 C3 174.6(3) . . . . ?
Cu1 O3 C3 C4 -163.8(2) . . . . ?
Cu1 O3 C3 C2 15.4(5) . . . . ?
C7 C2 C3 O3 -175.3(3) . . . . ?
N6 C2 C3 O3 7.8(5) . . . . ?
C7 C2 C3 C4 4.0(5) . . . . ?
N6 C2 C3 C4 -172.9(3) . . . . ?
O3 C3 C4 C5 173.8(3) . . . . ?
C2 C3 C4 C5 -5.5(5) . . . . ?
O3 C3 C4 N7 -5.6(5) . . . . ?
C2 C3 C4 N7 175.0(3) . . . . ?
O4 N7 C4 C5 143.6(4) . . . . ?
O5 N7 C4 C5 -34.5(5) . . . . ?
O4 N7 C4 C3 -36.9(5) . . . . ?
O5 N7 C4 C3 145.0(3) . . . . ?
C3 C4 C5 C6 3.5(5) . . . . ?
N7 C4 C5 C6 -177.0(3) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C4 C5 C6 N8 179.6(3) . . . . ?
O6 N8 C6 C7 -166.5(3) . . . . ?
O7 N8 C6 C7 13.6(5) . . . . ?
O6 N8 C6 C5 14.3(5) . . . . ?
O7 N8 C6 C5 -165.5(3) . . . . ?
C5 C6 C7 C2 -1.9(6) . . . . ?
N8 C6 C7 C2 179.0(3) . . . . ?
C3 C2 C7 C6 -0.6(5) . . . . ?
N6 C2 C7 C6 176.4(3) . . . . ?

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
N5 H5A O7 0.82(4) 2.40(4) 2.984(5) 129(3) 2_645
N5 H5A O6 0.82(4) 2.52(4) 3.057(5) 124(3) 3_666
N5 H5B N3 0.97(5) 2.18(5) 3.109(5) 159(4) 4_565

_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.
;



_refine_diff_density_max         0.390
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-4


####################################################################### 
# 
# 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_nx245
_database_code_depnum_ccdc_archive 'CCDC 1934803'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2018-06-30
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
di(1-amino-5-methyltetrazolyl) 5-hydroxy-2,4,6-trinitresorcinato copper(II)
;
_chemical_name_common            
;
di(1-amino-5-methyltetrazolyl) 5-hydroxy-2,4,6-trinitresorcinato copper(II)
;
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 Cu N13 O9'
_chemical_formula_sum            'C10 H11 Cu N13 O9'
_chemical_formula_weight         520.86

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'


_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+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.2566(9)
_cell_length_b                   14.7433(7)
_cell_length_c                   8.1350(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1829.83(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1448
_cell_measurement_theta_min      4.5660
_cell_measurement_theta_max      23.9630

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.463
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    1.279
_shelx_estimated_absorpt_T_min   0.589
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          ?
_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 ?
_diffrn_reflns_number            17850
_diffrn_reflns_av_unetI/netI     0.1609
_diffrn_reflns_av_R_equivalents  0.1214
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.239
_diffrn_reflns_theta_max         32.319
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             5814
_reflns_number_gt                3397
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_max     0.822
_reflns_Friedel_fraction_full    0.955

_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    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Encifer 1.5.1, CCDC 2014'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0178P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 923 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_refine_ls_abs_structure_Flack   0.003(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5814
_refine_ls_number_parameters     304
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1406
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000



_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
;



_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?

_diffrn_detector                 ?
_diffrn_detector_type            ?



_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?
_diffrn_measurement_details      ?



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_
_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 0.56830(5) 0.28428(4) 0.50618(11) 0.01633(17) Uani 1 1 d . . . . .
O1 O 0.5443(3) 0.4083(3) 0.5687(5) 0.0202(11) Uani 1 1 d . . . . .
O2 O 0.4212(3) 0.2750(3) 0.5225(9) 0.0272(12) Uani 1 1 d . . . . .
O3 O 0.3493(3) 0.2579(3) 0.7487(7) 0.0302(13) Uani 1 1 d . . . . .
O4 O 0.2590(3) 0.4015(3) 0.8045(7) 0.0234(12) Uani 1 1 d . . . . .
O5 O 0.2046(3) 0.5419(3) 0.9302(6) 0.0289(12) Uani 1 1 d . . . . .
O6 O 0.2818(3) 0.6653(3) 0.9385(5) 0.0208(11) Uani 1 1 d . . . . .
O7 O 0.4289(3) 0.6764(3) 0.7757(5) 0.0172(10) Uani 1 1 d . . . . .
O8 O 0.5462(3) 0.6526(3) 0.5113(9) 0.0373(13) Uani 1 1 d . . . . .
O9 O 0.6272(4) 0.5736(4) 0.6758(8) 0.0454(17) Uani 1 1 d . . . . .
N1 N 0.5717(4) 0.0362(3) 0.2820(7) 0.0175(12) Uani 1 1 d . . . . .
N2 N 0.6424(4) 0.0284(4) 0.3810(8) 0.0251(15) Uani 1 1 d . . . . .
N3 N 0.6464(4) 0.1025(4) 0.4645(7) 0.0251(15) Uani 1 1 d . . . . .
N4 N 0.5777(4) 0.1584(4) 0.4215(7) 0.0196(13) Uani 1 1 d . . . . .
N5 N 0.5489(4) -0.0288(4) 0.1659(7) 0.0258(15) Uani 1 1 d . . . . .
H5A H 0.586202 -0.045672 0.125508 0.031 Uiso 1 1 d R U . . .
H5B H 0.522845 -0.060284 0.243233 0.031 Uiso 1 1 d R U . . .
N6 N 0.6631(4) 0.2365(3) 0.9710(6) 0.0201(14) Uani 1 1 d . . . . .
N7 N 0.6094(4) 0.1635(4) 0.9537(6) 0.0199(13) Uani 1 1 d . . . . .
N8 N 0.5712(4) 0.1747(3) 0.8140(7) 0.0187(13) Uani 1 1 d . . . . .
N9 N 0.5992(4) 0.2529(4) 0.7392(7) 0.0189(13) Uani 1 1 d . . . . .
N10 N 0.7231(4) 0.2462(4) 1.0981(7) 0.0237(14) Uani 1 1 d . . . . .
H10B H 0.693047 0.246740 1.193399 0.028 Uiso 1 1 d R U . . .
H10A H 0.763146 0.201340 1.081302 0.028 Uiso 1 1 d R U . . .
N11 N 0.3875(4) 0.3062(4) 0.6503(8) 0.0222(14) Uani 1 1 d . . . . .
N12 N 0.2739(4) 0.5851(4) 0.8900(7) 0.0193(13) Uani 1 1 d . . . . .
N13 N 0.5566(4) 0.5926(4) 0.6136(8) 0.0251(15) Uani 1 1 d . . . . .
C1 C 0.5321(4) 0.1155(4) 0.3051(8) 0.0173(14) Uani 1 1 d . . . . .
C2 C 0.4516(4) 0.1463(5) 0.2188(9) 0.0235(17) Uani 1 1 d . . . . .
H2A H 0.404219 0.154433 0.298789 0.035 Uiso 1 1 calc R U . . .
H2B H 0.434270 0.100743 0.137373 0.035 Uiso 1 1 calc R U . . .
H2C H 0.463247 0.204078 0.163328 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6562(4) 0.2909(4) 0.8405(8) 0.0166(14) Uani 1 1 d . . . . .
C4 C 0.7025(5) 0.3790(4) 0.8252(9) 0.0244(16) Uani 1 1 d . . . . .
H4A H 0.742485 0.376865 0.731017 0.037 Uiso 1 1 calc R U . . .
H4B H 0.735979 0.390792 0.925731 0.037 Uiso 1 1 calc R U . . .
H4C H 0.659524 0.427599 0.808724 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4770(5) 0.4477(4) 0.6311(8) 0.0163(15) Uani 1 1 d . . . . .
C6 C 0.3966(5) 0.4022(4) 0.6782(8) 0.0155(14) Uani 1 1 d . . . . .
C7 C 0.3299(4) 0.4475(5) 0.7607(9) 0.0188(15) Uani 1 1 d . . . . .
C8 C 0.3379(4) 0.5423(4) 0.7954(8) 0.0185(14) Uani 1 1 d . . . . .
C9 C 0.4157(4) 0.5917(4) 0.7445(8) 0.0176(15) Uani 1 1 d . . . . .
C10 C 0.4781(4) 0.5404(4) 0.6634(8) 0.0169(15) Uani 1 1 d . . . . .
H4 H 0.223(5) 0.439(5) 0.832(10) 0.04(3) Uiso 1 1 d . . . . .


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 O1 1.934(4) . ?
Cu1 O7 1.963(4) 2_664 ?
Cu1 N4 1.985(5) . ?
Cu1 N9 2.007(6) . ?
Cu1 O2 2.253(4) . ?
O1 C5 1.283(8) . ?
O2 N11 1.248(8) . ?
O3 N11 1.219(7) . ?
O4 C7 1.326(8) . ?
O4 H4 0.81(7) . ?
O5 N12 1.277(7) . ?
O6 N12 1.252(6) . ?
O7 C9 1.291(7) . ?
O8 N13 1.226(8) . ?
O9 N13 1.222(8) . ?
N1 C1 1.330(8) . ?
N1 N2 1.351(8) . ?
N1 N5 1.391(7) . ?
N2 N3 1.289(7) . ?
N3 N4 1.378(7) . ?
N4 C1 1.334(8) . ?
N5 H5A 0.7025 . ?
N5 H5B 0.8770 . ?
N6 C3 1.335(8) . ?
N6 N7 1.358(7) . ?
N6 N10 1.388(7) . ?
N7 N8 1.288(7) . ?
N8 N9 1.372(7) . ?
N9 C3 1.323(8) . ?
N10 H10B 0.9003 . ?
N10 H10A 0.9107 . ?
N11 C6 1.440(8) . ?
N12 C8 1.395(8) . ?
N13 C10 1.479(8) . ?
C1 C2 1.486(9) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.484(9) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.393(8) . ?
C5 C6 1.449(9) . ?
C6 C7 1.391(9) . ?
C7 C8 1.430(9) . ?
C8 C9 1.453(9) . ?
C9 C10 1.384(9) . ?

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
O1 Cu1 O7 88.64(18) . 2_664 ?
O1 Cu1 N4 171.7(2) . . ?
O7 Cu1 N4 86.7(2) 2_664 . ?
O1 Cu1 N9 90.8(2) . . ?
O7 Cu1 N9 164.8(2) 2_664 . ?
N4 Cu1 N9 95.5(2) . . ?
O1 Cu1 O2 81.56(17) . . ?
O7 Cu1 O2 95.5(2) 2_664 . ?
N4 Cu1 O2 92.0(2) . . ?
N9 Cu1 O2 99.4(2) . . ?
C5 O1 Cu1 133.1(4) . . ?
N11 O2 Cu1 115.9(5) . . ?
C7 O4 H4 106(6) . . ?
C9 O7 Cu1 118.4(4) . 2_665 ?
C1 N1 N2 110.7(5) . . ?
C1 N1 N5 126.1(6) . . ?
N2 N1 N5 123.1(5) . . ?
N3 N2 N1 106.2(5) . . ?
N2 N3 N4 109.7(5) . . ?
C1 N4 N3 107.1(5) . . ?
C1 N4 Cu1 130.6(5) . . ?
N3 N4 Cu1 121.7(4) . . ?
N1 N5 H5A 111.0 . . ?
N1 N5 H5B 89.5 . . ?
H5A N5 H5B 121.0 . . ?
C3 N6 N7 110.2(5) . . ?
C3 N6 N10 125.6(5) . . ?
N7 N6 N10 123.8(5) . . ?
N8 N7 N6 105.3(5) . . ?
N7 N8 N9 111.0(5) . . ?
C3 N9 N8 106.5(6) . . ?
C3 N9 Cu1 130.2(5) . . ?
N8 N9 Cu1 122.7(4) . . ?
N6 N10 H10B 107.8 . . ?
N6 N10 H10A 104.8 . . ?
H10B N10 H10A 118.5 . . ?
O3 N11 O2 121.9(6) . . ?
O3 N11 C6 121.1(6) . . ?
O2 N11 C6 117.0(6) . . ?
O6 N12 O5 118.0(6) . . ?
O6 N12 C8 122.3(6) . . ?
O5 N12 C8 119.7(5) . . ?
O9 N13 O8 124.1(6) . . ?
O9 N13 C10 118.8(6) . . ?
O8 N13 C10 117.2(6) . . ?
N1 C1 N4 106.2(6) . . ?
N1 C1 C2 125.3(6) . . ?
N4 C1 C2 128.5(6) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N9 C3 N6 107.0(6) . . ?
N9 C3 C4 129.1(6) . . ?
N6 C3 C4 123.7(6) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 C10 120.5(6) . . ?
O1 C5 C6 124.9(6) . . ?
C10 C5 C6 114.5(6) . . ?
C7 C6 N11 118.5(6) . . ?
C7 C6 C5 121.6(6) . . ?
N11 C6 C5 119.7(6) . . ?
O4 C7 C6 118.8(6) . . ?
O4 C7 C8 121.1(6) . . ?
C6 C7 C8 120.1(6) . . ?
N12 C8 C7 119.5(6) . . ?
N12 C8 C9 120.1(6) . . ?
C7 C8 C9 120.2(6) . . ?
O7 C9 C10 121.0(6) . . ?
O7 C9 C8 123.9(6) . . ?
C10 C9 C8 115.1(6) . . ?
C9 C10 C5 128.2(6) . . ?
C9 C10 N13 113.8(5) . . ?
C5 C10 N13 118.0(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
C1 N1 N2 N3 -0.1(8) . . . . ?
N5 N1 N2 N3 176.2(6) . . . . ?
N1 N2 N3 N4 0.7(7) . . . . ?
N2 N3 N4 C1 -1.1(7) . . . . ?
N2 N3 N4 Cu1 -173.4(4) . . . . ?
C3 N6 N7 N8 0.0(7) . . . . ?
N10 N6 N7 N8 -173.2(6) . . . . ?
N6 N7 N8 N9 0.5(7) . . . . ?
N7 N8 N9 C3 -0.8(7) . . . . ?
N7 N8 N9 Cu1 170.7(4) . . . . ?
Cu1 O2 N11 O3 -114.8(6) . . . . ?
Cu1 O2 N11 C6 64.5(7) . . . . ?
N2 N1 C1 N4 -0.6(8) . . . . ?
N5 N1 C1 N4 -176.7(6) . . . . ?
N2 N1 C1 C2 -179.0(6) . . . . ?
N5 N1 C1 C2 4.8(11) . . . . ?
N3 N4 C1 N1 1.0(7) . . . . ?
Cu1 N4 C1 N1 172.4(5) . . . . ?
N3 N4 C1 C2 179.4(6) . . . . ?
Cu1 N4 C1 C2 -9.2(11) . . . . ?
N8 N9 C3 N6 0.8(7) . . . . ?
Cu1 N9 C3 N6 -169.9(4) . . . . ?
N8 N9 C3 C4 -176.0(6) . . . . ?
Cu1 N9 C3 C4 13.3(11) . . . . ?
N7 N6 C3 N9 -0.5(7) . . . . ?
N10 N6 C3 N9 172.5(6) . . . . ?
N7 N6 C3 C4 176.5(6) . . . . ?
N10 N6 C3 C4 -10.5(10) . . . . ?
Cu1 O1 C5 C10 -179.7(5) . . . . ?
Cu1 O1 C5 C6 2.3(10) . . . . ?
O3 N11 C6 C7 -32.8(9) . . . . ?
O2 N11 C6 C7 148.0(7) . . . . ?
O3 N11 C6 C5 142.8(7) . . . . ?
O2 N11 C6 C5 -36.4(9) . . . . ?
O1 C5 C6 C7 173.2(6) . . . . ?
C10 C5 C6 C7 -4.8(10) . . . . ?
O1 C5 C6 N11 -2.2(10) . . . . ?
C10 C5 C6 N11 179.7(6) . . . . ?
N11 C6 C7 O4 -2.7(10) . . . . ?
C5 C6 C7 O4 -178.1(6) . . . . ?
N11 C6 C7 C8 178.0(6) . . . . ?
C5 C6 C7 C8 2.5(10) . . . . ?
O6 N12 C8 C7 172.5(6) . . . . ?
O5 N12 C8 C7 -7.2(9) . . . . ?
O6 N12 C8 C9 -2.2(10) . . . . ?
O5 N12 C8 C9 178.0(6) . . . . ?
O4 C7 C8 N12 6.0(10) . . . . ?
C6 C7 C8 N12 -174.7(6) . . . . ?
O4 C7 C8 C9 -179.2(6) . . . . ?
C6 C7 C8 C9 0.1(10) . . . . ?
Cu1 O7 C9 C10 -118.3(6) 2_665 . . . ?
Cu1 O7 C9 C8 59.4(8) 2_665 . . . ?
N12 C8 C9 O7 -3.1(10) . . . . ?
C7 C8 C9 O7 -177.8(6) . . . . ?
N12 C8 C9 C10 174.7(6) . . . . ?
C7 C8 C9 C10 0.0(9) . . . . ?
O7 C9 C10 C5 174.9(7) . . . . ?
C8 C9 C10 C5 -2.9(11) . . . . ?
O7 C9 C10 N13 -2.0(9) . . . . ?
C8 C9 C10 N13 -179.9(6) . . . . ?
O1 C5 C10 C9 -172.9(7) . . . . ?
C6 C5 C10 C9 5.3(11) . . . . ?
O1 C5 C10 N13 3.9(10) . . . . ?
C6 C5 C10 N13 -177.9(6) . . . . ?
O9 N13 C10 C9 115.0(7) . . . . ?
O8 N13 C10 C9 -65.0(8) . . . . ?
O9 N13 C10 C5 -62.3(9) . . . . ?
O8 N13 C10 C5 117.8(7) . . . . ?

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
? ? ? ? ? ? ? ?





_refine_diff_density_max         0.742
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.122

_shelxl_version_number           ?


####################################################################### 
# 
# 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_nx457
_database_code_depnum_ccdc_archive 'CCDC 1934808'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2018-11-27
_audit_creation_method           SHELXL-2018/3


_chemical_name_systematic        
' (E)-1-phenyl-N-(5-methyl-1H-tetrazol-1-yl)methanimine '
_chemical_name_common            '1-amino-5-methyl-tetrazole benzhydrazone'
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C9 H9 N5'
_chemical_formula_sum            'C9 H9 N5'
_chemical_formula_weight         187.21

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14
_symmetry_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                   11.5832(8)
_cell_length_b                   7.4944(4)
_cell_length_c                   11.9045(8)
_cell_angle_alpha                90
_cell_angle_beta                 118.862(9)
_cell_angle_gamma                90
_cell_volume                     905.05(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    129(2)
_cell_measurement_reflns_used    3593
_cell_measurement_theta_min      3.9080
_cell_measurement_theta_max      32.2000

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.335
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.45633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           ?


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      129(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_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            9657
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_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         3.380
_diffrn_reflns_theta_max         32.222
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2995
_reflns_number_gt                2511
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Encifer 1.5.1, CCDC 2014'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0673P)²+0.2054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2995
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000



_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
;



_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      -0.0276361000
_diffrn_orient_matrix_UB_12      -0.0309942000
_diffrn_orient_matrix_UB_13      -0.0640954000
_diffrn_orient_matrix_UB_21      0.0613638000
_diffrn_orient_matrix_UB_22      0.0134223000
_diffrn_orient_matrix_UB_23      0.0015232000
_diffrn_orient_matrix_UB_31      0.0189952000
_diffrn_orient_matrix_UB_32      -0.0884268000
_diffrn_orient_matrix_UB_33      0.0227118000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00 -57.00   1.00   10.00    --  -28.86-178.00  30.00   26
  2  ω    -98.00 -17.00   1.00   10.00    --  -28.86 -57.00   0.00   81
  3  ω    -17.00  40.00   1.00   10.00    --  -28.86  57.00 150.00   57
  4  ω     -3.00  97.00   1.00   10.00    --   30.11  77.00-120.00  100
  5  ω    -24.00   1.00   1.00   10.00    --   30.11 -99.00-120.00   25
  6  ω    -23.00  67.00   1.00   10.00    --   30.11 -99.00 120.00   90
  7  ω    -25.00  73.00   1.00   10.00    --   30.11 -99.00 -30.00   98
;



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'
N N 0.0061 0.0033 '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_
_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 0.70356(8) 0.11146(11) 0.35935(7) 0.01582(17) Uani 1 1 d . . . . .
N2 N 0.67370(9) 0.00633(12) 0.25614(8) 0.02109(19) Uani 1 1 d . . . . .
N3 N 0.78315(9) -0.01186(12) 0.25278(8) 0.0237(2) Uani 1 1 d . . . . .
N4 N 0.88424(8) 0.07852(12) 0.35105(8) 0.02177(19) Uani 1 1 d . . . . .
N5 N 0.61623(8) 0.17021(11) 0.39913(7) 0.01700(17) Uani 1 1 d . . . . .
C1 C 0.83241(9) 0.15573(12) 0.41591(9) 0.01767(19) Uani 1 1 d . . . . .
C2 C 0.89906(10) 0.27161(14) 0.52993(10) 0.0236(2) Uani 1 1 d . . . . .
H2A H 0.835565 0.309513 0.557373 0.035 Uiso 0.5 1 calc R U P . .
H2B H 0.970987 0.205414 0.599535 0.035 Uiso 0.5 1 calc R U P . .
H2C H 0.934867 0.376813 0.508535 0.035 Uiso 0.5 1 calc R U P . .
H2D H 0.992048 0.284981 0.552922 0.035 Uiso 0.5 1 calc R U P . .
H2E H 0.856625 0.389080 0.510761 0.035 Uiso 0.5 1 calc R U P . .
H2F H 0.892745 0.217681 0.601761 0.035 Uiso 0.5 1 calc R U P . .
C3 C 0.50142(9) 0.09870(12) 0.34293(8) 0.01695(18) Uani 1 1 d . . . . .
H3 H 0.481260 0.010987 0.278473 0.020 Uiso 1 1 calc R U . . .
C4 C 0.40154(9) 0.15194(12) 0.37788(8) 0.01667(19) Uani 1 1 d . . . . .
C5 C 0.43001(10) 0.27013(13) 0.47912(9) 0.01973(19) Uani 1 1 d . . . . .
H5 H 0.515835 0.319662 0.526314 0.024 Uiso 1 1 calc R U . . .
C6 C 0.33275(11) 0.31480(14) 0.51042(10) 0.0244(2) Uani 1 1 d . . . . .
H6 H 0.351986 0.395065 0.579004 0.029 Uiso 1 1 calc R U . . .
C7 C 0.20670(11) 0.24193(15) 0.44125(11) 0.0257(2) Uani 1 1 d . . . . .
H7 H 0.140408 0.272623 0.463062 0.031 Uiso 1 1 calc R U . . .
C8 C 0.17773(10) 0.12502(15) 0.34089(11) 0.0251(2) Uani 1 1 d . . . . .
H8 H 0.091660 0.076223 0.293734 0.030 Uiso 1 1 calc R U . . .
C9 C 0.27506(10) 0.07923(14) 0.30931(9) 0.0215(2) Uani 1 1 d . . . . .
H9 H 0.255472 -0.001659 0.240979 0.026 Uiso 1 1 calc R U . . .


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 C1 1.3493(12) . ?
N1 N2 1.3564(11) . ?
N1 N5 1.3798(11) . ?
N2 N3 1.2948(12) . ?
N3 N4 1.3697(12) . ?
N4 C1 1.3187(12) . ?
N5 C3 1.2823(12) . ?
C1 C2 1.4769(13) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?
C2 H2F 0.9800 . ?
C3 C4 1.4613(13) . ?
C3 H3 0.9500 . ?
C4 C9 1.3982(13) . ?
C4 C5 1.4008(13) . ?
C5 C6 1.3876(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.3955(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3859(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3926(14) . ?
C8 H8 0.9500 . ?
C9 H9 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 N1 N2 109.38(8) . . ?
C1 N1 N5 124.60(8) . . ?
N2 N1 N5 125.99(8) . . ?
N3 N2 N1 105.30(8) . . ?
N2 N3 N4 111.57(8) . . ?
C1 N4 N3 105.90(8) . . ?
C3 N5 N1 115.79(8) . . ?
N4 C1 N1 107.85(8) . . ?
N4 C1 C2 127.76(9) . . ?
N1 C1 C2 124.39(9) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
H2D C2 H2E 109.5 . . ?
H2D C2 H2F 109.5 . . ?
H2E C2 H2F 109.5 . . ?
N5 C3 C4 120.10(8) . . ?
N5 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C9 C4 C5 119.60(9) . . ?
C9 C4 C3 118.54(8) . . ?
C5 C4 C3 121.85(8) . . ?
C6 C5 C4 119.94(9) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.07(10) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.34(9) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.86(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 120.20(9) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?

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
C1 N1 N2 N3 0.47(10) . . . . ?
N5 N1 N2 N3 178.44(8) . . . . ?
N1 N2 N3 N4 0.00(11) . . . . ?
N2 N3 N4 C1 -0.47(11) . . . . ?
C1 N1 N5 C3 -172.47(8) . . . . ?
N2 N1 N5 C3 9.86(13) . . . . ?
N3 N4 C1 N1 0.73(10) . . . . ?
N3 N4 C1 C2 -178.95(9) . . . . ?
N2 N1 C1 N4 -0.77(11) . . . . ?
N5 N1 C1 N4 -178.77(8) . . . . ?
N2 N1 C1 C2 178.93(9) . . . . ?
N5 N1 C1 C2 0.93(15) . . . . ?
N1 N5 C3 C4 -179.88(7) . . . . ?
N5 C3 C4 C9 176.18(8) . . . . ?
N5 C3 C4 C5 -5.12(14) . . . . ?
C9 C4 C5 C6 -0.24(14) . . . . ?
C3 C4 C5 C6 -178.93(9) . . . . ?
C4 C5 C6 C7 0.08(15) . . . . ?
C5 C6 C7 C8 -0.13(16) . . . . ?
C6 C7 C8 C9 0.35(16) . . . . ?
C7 C8 C9 C4 -0.51(15) . . . . ?
C5 C4 C9 C8 0.46(14) . . . . ?
C3 C4 C9 C8 179.19(9) . . . . ?

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
C2 H2B N4 0.98 2.59 3.4293(14) 143.1 3_756




_refine_diff_density_max         0.433
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.056

_shelxl_version_number           ?


####################################################################### 
# 
# 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_lx577
_database_code_depnum_ccdc_archive 'CCDC 1934811'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             
;
'Wed Nov 30 11:47:19 2016'
;
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
bis(2-aminotetrazolyl) bis(trinitroresorcinyl) copper(II)
;
_chemical_name_common            
'bis(2-aminotetrazolyl) bis(trinitroresorcinyl) copper(II)'
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 Cu N16 O16'
_chemical_formula_weight         721.92

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_symmetry_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                   6.2297(4)
_cell_length_b                   8.8060(6)
_cell_length_c                   12.0376(7)
_cell_angle_alpha                79.309(5)
_cell_angle_beta                 89.906(5)
_cell_angle_gamma                82.408(5)
_cell_volume                     643.04(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2419
_cell_measurement_theta_min      4.7220
_cell_measurement_theta_max      31.8090

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.961
_shelx_estimated_absorpt_T_min   0.717
_shelx_estimated_absorpt_T_max   0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98820
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           ?


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_F_000             363
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            4991
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.319
_diffrn_reflns_theta_max         26.372
_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             2612
_reflns_number_gt                2390
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Microsoft Word 2016'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²+0.2563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2612
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000



_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
;



_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      -0.0408974000
_diffrn_orient_matrix_UB_12      0.0325066000
_diffrn_orient_matrix_UB_13      -0.0554721000
_diffrn_orient_matrix_UB_21      0.0150652000
_diffrn_orient_matrix_UB_22      0.0753800000
_diffrn_orient_matrix_UB_23      0.0087757000
_diffrn_orient_matrix_UB_31      0.1063102000
_diffrn_orient_matrix_UB_32      -0.0101700000
_diffrn_orient_matrix_UB_33      -0.0210613000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    6.00   96.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -21.00    5.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   50.00   75.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -24.00   51.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000  120.0000 75

#__ type_ start__ end____ width___ exp.time_
  5 omega  -41.00   53.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -57.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  7 omega  -94.00  -43.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  -57.0000  120.0000 51

;



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_
_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
Cu Cu 0.000000 1.000000 0.000000 0.01705(10) Uani 1 2 d S . P . .
O1 O -0.0738(2) 1.00229(15) 0.15645(10) 0.0207(3) Uani 1 1 d . . . . .
O2 O 0.3134(2) 0.84825(17) 0.09821(11) 0.0276(3) Uani 1 1 d . . . . .
O3 O 0.4373(3) 0.6331(2) 0.20891(14) 0.0486(5) Uani 1 1 d . . . . .
O5 O -0.3328(3) 1.17530(18) 0.32445(15) 0.0419(4) Uani 1 1 d . . . . .
O6 O -0.5137(2) 0.99400(18) 0.29686(13) 0.0317(3) Uani 1 1 d . . . . .
O7 O -0.2688(3) 0.8624(2) 0.52778(13) 0.0395(4) Uani 1 1 d . . . . .
O8 O -0.0273(3) 0.6332(2) 0.65317(12) 0.0393(4) Uani 1 1 d . . . . .
O9 O 0.2610(3) 0.5184(2) 0.58945(14) 0.0427(4) Uani 1 1 d . . . . .
N1 N 0.3212(3) 1.36756(19) 0.04720(13) 0.0245(4) Uani 1 1 d . . . . .
N2 N 0.2160(2) 1.41524(17) -0.05137(12) 0.0173(3) Uani 1 1 d . . . . .
N3 N 0.1065(2) 1.31478(18) -0.08407(13) 0.0203(3) Uani 1 1 d . . . . .
N4 N 0.1411(2) 1.18977(17) -0.00137(13) 0.0195(3) Uani 1 1 d . . . . .
N5 N 0.2078(3) 1.56689(19) -0.10958(15) 0.0226(4) Uani 1 1 d . . . . .
N6 N 0.3123(3) 0.7539(2) 0.18865(14) 0.0248(4) Uani 1 1 d . . . . .
N7 N -0.3467(3) 1.04002(19) 0.32076(13) 0.0213(3) Uani 1 1 d . . . . .
N8 N 0.1024(3) 0.6175(2) 0.57561(15) 0.0302(4) Uani 1 1 d . . . . .
C1 C 0.2699(3) 1.2242(2) 0.07559(17) 0.0245(4) Uani 1 1 d . . . . .
C2 C -0.0204(3) 0.9099(2) 0.24966(15) 0.0170(4) Uani 1 1 d . . . . .
C3 C -0.1529(3) 0.9242(2) 0.34397(15) 0.0190(4) Uani 1 1 d . . . . .
C4 C -0.1237(3) 0.8344(2) 0.45031(16) 0.0230(4) Uani 1 1 d . . . . .
C5 C 0.0582(3) 0.7185(2) 0.46790(16) 0.0235(4) Uani 1 1 d . . . . .
C6 C 0.1960(3) 0.6965(2) 0.37996(17) 0.0229(4) Uani 1 1 d . . . . .
C7 C 0.1591(3) 0.7878(2) 0.27423(15) 0.0197(4) Uani 1 1 d . . . . .
H6 H 0.310(3) 0.621(2) 0.3941(17) 0.021(5) Uiso 1 1 d . . . . .
H1 H 0.317(4) 1.161(3) 0.137(2) 0.034(6) Uiso 1 1 d . . . . .
H5A H 0.170(4) 1.567(3) -0.174(2) 0.026(6) Uiso 1 1 d . . . . .
H7 H -0.226(5) 0.799(3) 0.587(3) 0.055(9) Uiso 1 1 d . . . . .
H5B H 0.341(4) 1.589(3) -0.108(2) 0.038(7) Uiso 1 1 d . . . . .


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
Cu O1 1.9409(12) . ?
Cu O1 1.9409(12) 2_575 ?
Cu N4 1.9856(15) 2_575 ?
Cu N4 1.9857(15) . ?
Cu O2 2.3931(14) . ?
Cu O2 2.3931(14) 2_575 ?
O1 C2 1.274(2) . ?
O2 N6 1.242(2) . ?
O3 N6 1.218(2) . ?
O5 N7 1.215(2) . ?
O6 N7 1.219(2) . ?
O7 C4 1.331(2) . ?
O7 H7 0.84(3) . ?
O8 N8 1.249(2) . ?
O9 N8 1.218(2) . ?
N1 N2 1.326(2) . ?
N1 C1 1.327(2) . ?
N2 N3 1.301(2) . ?
N2 N5 1.383(2) . ?
N3 N4 1.334(2) . ?
N4 C1 1.328(2) . ?
N5 H5A 0.81(2) . ?
N5 H5B 0.88(3) . ?
N6 C7 1.448(2) . ?
N7 C3 1.465(2) . ?
N8 C5 1.434(2) . ?
C1 H1 0.86(2) . ?
C2 C3 1.417(2) . ?
C2 C7 1.435(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.410(3) . ?
C5 C6 1.387(3) . ?
C6 C7 1.375(3) . ?
C6 H6 0.90(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
O1 Cu O1 180.00(8) . 2_575 ?
O1 Cu N4 91.28(6) . 2_575 ?
O1 Cu N4 88.72(6) 2_575 2_575 ?
O1 Cu N4 88.72(6) . . ?
O1 Cu N4 91.28(6) 2_575 . ?
N4 Cu N4 180.0 2_575 . ?
O1 Cu O2 78.44(5) . . ?
O1 Cu O2 101.56(5) 2_575 . ?
N4 Cu O2 91.34(6) 2_575 . ?
N4 Cu O2 88.66(6) . . ?
O1 Cu O2 101.56(5) . 2_575 ?
O1 Cu O2 78.44(5) 2_575 2_575 ?
N4 Cu O2 88.66(6) 2_575 2_575 ?
N4 Cu O2 91.34(6) . 2_575 ?
O2 Cu O2 180.0 . 2_575 ?
C2 O1 Cu 133.88(12) . . ?
N6 O2 Cu 125.44(11) . . ?
C4 O7 H7 106(2) . . ?
N2 N1 C1 100.81(15) . . ?
N3 N2 N1 115.66(15) . . ?
N3 N2 N5 122.50(15) . . ?
N1 N2 N5 121.56(15) . . ?
N2 N3 N4 104.17(14) . . ?
C1 N4 N3 107.12(15) . . ?
C1 N4 Cu 130.01(13) . . ?
N3 N4 Cu 122.76(12) . . ?
N2 N5 H5A 106.7(16) . . ?
N2 N5 H5B 105.5(16) . . ?
H5A N5 H5B 110(2) . . ?
O3 N6 O2 122.34(17) . . ?
O3 N6 C7 118.21(17) . . ?
O2 N6 C7 119.45(16) . . ?
O5 N7 O6 123.66(17) . . ?
O5 N7 C3 119.14(16) . . ?
O6 N7 C3 117.18(16) . . ?
O9 N8 O8 121.64(18) . . ?
O9 N8 C5 120.28(18) . . ?
O8 N8 C5 118.08(18) . . ?
N1 C1 N4 112.23(18) . . ?
N1 C1 H1 123.1(15) . . ?
N4 C1 H1 124.7(15) . . ?
O1 C2 C3 117.89(17) . . ?
O1 C2 C7 128.79(17) . . ?
C3 C2 C7 113.31(16) . . ?
C4 C3 C2 126.42(18) . . ?
C4 C3 N7 118.25(16) . . ?
C2 C3 N7 115.18(16) . . ?
O7 C4 C3 117.91(18) . . ?
O7 C4 C5 125.37(18) . . ?
C3 C4 C5 116.72(17) . . ?
C6 C5 C4 120.51(18) . . ?
C6 C5 N8 118.30(18) . . ?
C4 C5 N8 121.16(18) . . ?
C7 C6 C5 120.87(19) . . ?
C7 C6 H6 121.1(13) . . ?
C5 C6 H6 118.1(13) . . ?
C6 C7 C2 122.15(18) . . ?
C6 C7 N6 116.16(17) . . ?
C2 C7 N6 121.68(16) . . ?

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 N1 N2 N3 0.3(2) . . . . ?
C1 N1 N2 N5 174.48(17) . . . . ?
N1 N2 N3 N4 -0.2(2) . . . . ?
N5 N2 N3 N4 -174.26(15) . . . . ?
N2 N3 N4 C1 -0.07(19) . . . . ?
N2 N3 N4 Cu 176.48(11) . . . . ?
Cu O2 N6 O3 143.99(16) . . . . ?
Cu O2 N6 C7 -36.5(2) . . . . ?
N2 N1 C1 N4 -0.4(2) . . . . ?
N3 N4 C1 N1 0.3(2) . . . . ?
Cu N4 C1 N1 -175.92(13) . . . . ?
Cu O1 C2 C3 -161.64(12) . . . . ?
Cu O1 C2 C7 17.6(3) . . . . ?
O1 C2 C3 C4 179.00(17) . . . . ?
C7 C2 C3 C4 -0.4(3) . . . . ?
O1 C2 C3 N7 3.5(2) . . . . ?
C7 C2 C3 N7 -175.86(15) . . . . ?
O5 N7 C3 C4 98.5(2) . . . . ?
O6 N7 C3 C4 -82.6(2) . . . . ?
O5 N7 C3 C2 -85.6(2) . . . . ?
O6 N7 C3 C2 93.23(19) . . . . ?
C2 C3 C4 O7 -178.21(18) . . . . ?
N7 C3 C4 O7 -2.9(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
N7 C3 C4 C5 176.65(16) . . . . ?
O7 C4 C5 C6 178.15(19) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
O7 C4 C5 N8 0.0(3) . . . . ?
C3 C4 C5 N8 -179.47(17) . . . . ?
O9 N8 C5 C6 2.1(3) . . . . ?
O8 N8 C5 C6 -176.91(18) . . . . ?
O9 N8 C5 C4 -179.67(19) . . . . ?
O8 N8 C5 C4 1.3(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
N8 C5 C6 C7 178.70(17) . . . . ?
C5 C6 C7 C2 0.5(3) . . . . ?
C5 C6 C7 N6 -179.57(17) . . . . ?
O1 C2 C7 C6 -179.84(18) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
O1 C2 C7 N6 0.2(3) . . . . ?
C3 C2 C7 N6 179.52(16) . . . . ?
O3 N6 C7 C6 12.7(3) . . . . ?
O2 N6 C7 C6 -166.79(17) . . . . ?
O3 N6 C7 C2 -167.38(18) . . . . ?
O2 N6 C7 C2 13.1(3) . . . . ?

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
N5 H5A O8 0.81(2) 2.36(3) 3.132(2) 161(2) 1_564




_refine_diff_density_max         0.309
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.059

_shelxl_version_number           ?


####################################################################### 
# 
# 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_nx254
_database_code_depnum_ccdc_archive 'CCDC 1934804'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2018-07-04
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
'bis(1-amino-5-methyltetrazolyl)copper(II) di(3,5-dihydroxy-2,4,6-trinitrophenolate)'
_chemical_name_common            
'bis(1-amino-5-methyltetrazolyl)copper(II) di(3,5-dihydroxy-2,4,6-trinitrophenolate)'
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Cu N16 O18'
_chemical_formula_weight         781.97

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_symmetry_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                   8.0087(9)
_cell_length_b                   8.7623(10)
_cell_length_c                   11.2661(9)
_cell_angle_alpha                69.572(9)
_cell_angle_beta                 78.715(8)
_cell_angle_gamma                64.890(11)
_cell_volume                     669.80(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1211
_cell_measurement_theta_min      4.6580
_cell_measurement_theta_max      29.0130

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    0.936
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95696
_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.
;

_exptl_special_details           
;
 ?
;


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_F_000             395
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_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            4191
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0759
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.094
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2712
_reflns_number_gt                2184
_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    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'enCIFer 1.5.1 (CCDC 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0281P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2712
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      -0.0413963000
_diffrn_orient_matrix_UB_12      -0.0569613000
_diffrn_orient_matrix_UB_13      -0.0006663000
_diffrn_orient_matrix_UB_21      0.0823859000
_diffrn_orient_matrix_UB_22      -0.0741639000
_diffrn_orient_matrix_UB_23      0.0208821000
_diffrn_orient_matrix_UB_31      -0.0331050000
_diffrn_orient_matrix_UB_32      -0.0059081000
_diffrn_orient_matrix_UB_33      0.0639641000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00   0.00   1.00   19.00    --  -24.10 -57.00 120.00   94
  2  ω    -25.00  17.00   1.00   19.00    --  -24.10 -99.00  60.00   42
  3  ω    -48.00  46.00   1.00   19.00    --  -24.10  57.00 -90.00   94
  4  ω    -17.00  19.00   1.00   19.00    --  -24.10 -99.00 -90.00   36
  5  ω     -2.00  95.00   1.00   19.00    --   25.35  38.00  60.00   97
;



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_
_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 0.0000 0.5000 0.0000 0.01557(16) Uani 1 2 d S . P . .
O1 O 0.0668(3) 0.3791(3) 0.17262(17) 0.0183(5) Uani 1 1 d . . . . .
O2 O -0.0084(3) 0.7397(3) 0.05398(17) 0.0202(5) Uani 1 1 d . . . . .
O3 O -0.1700(3) 0.8674(3) 0.19446(19) 0.0305(6) Uani 1 1 d . . . . .
O4 O 0.0794(3) 0.7897(3) 0.3527(2) 0.0265(5) Uani 1 1 d . . . . .
O5 O 0.2552(4) 0.6560(3) 0.5536(2) 0.0334(6) Uani 1 1 d . . . . .
O6 O 0.3781(3) 0.3744(3) 0.6396(2) 0.0314(6) Uani 1 1 d . . . . .
O7 O 0.3669(3) 0.1583(3) 0.5425(2) 0.0263(6) Uani 1 1 d . . . . .
O8 O 0.1730(4) 0.0206(3) 0.4354(2) 0.0358(6) Uani 1 1 d . . . . .
O9 O 0.3658(3) 0.0482(3) 0.27308(19) 0.0285(5) Uani 1 1 d . . . . .
N1 N 0.5396(4) 0.4340(3) -0.1500(2) 0.0209(6) Uani 1 1 d . . . . .
N2 N 0.5398(3) 0.2733(3) -0.0914(2) 0.0180(5) Uani 1 1 d . . . . .
N3 N 0.3817(3) 0.2677(3) -0.0363(2) 0.0195(6) Uani 1 1 d . . . . .
N4 N 0.2686(3) 0.4362(3) -0.0615(2) 0.0181(6) Uani 1 1 d . . . . .
N5 N 0.7024(4) 0.1241(4) -0.0877(3) 0.0243(6) Uani 1 1 d . . . . .
N6 N -0.0456(4) 0.7437(3) 0.1656(2) 0.0176(5) Uani 1 1 d . . . . .
N7 N 0.2905(4) 0.5046(3) 0.5525(2) 0.0219(6) Uani 1 1 d . . . . .
N8 N 0.2545(4) 0.1034(3) 0.3555(2) 0.0213(6) Uani 1 1 d . . . . .
C1 C 0.3646(4) 0.5360(4) -0.1317(3) 0.0185(7) Uani 1 1 d . . . . .
C2 C 0.2888(5) 0.7310(4) -0.1823(3) 0.0255(7) Uani 1 1 d . . . . .
H2A H 0.3904 0.7722 -0.2078 0.038 Uiso 1 1 calc R U . . .
H2B H 0.2082 0.7817 -0.1166 0.038 Uiso 1 1 calc R U . . .
H2C H 0.2175 0.7683 -0.2560 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1140(4) 0.4203(4) 0.2556(2) 0.0145(6) Uani 1 1 d . . . . .
C4 C 0.0629(4) 0.5931(4) 0.2631(2) 0.0160(6) Uani 1 1 d . . . . .
C5 C 0.1216(4) 0.6249(4) 0.3584(3) 0.0178(6) Uani 1 1 d . . . . .
C6 C 0.2282(4) 0.4775(4) 0.4554(2) 0.0169(6) Uani 1 1 d . . . . .
C7 C 0.2728(4) 0.3025(4) 0.4546(3) 0.0171(6) Uani 1 1 d . . . . .
C8 C 0.2157(4) 0.2819(4) 0.3563(3) 0.0160(6) Uani 1 1 d . . . . .
H5A H 0.712(5) 0.057(5) -0.011(4) 0.042(12) Uiso 1 1 d . . . . .
H5B H 0.699(6) 0.074(5) -0.144(4) 0.053(12) Uiso 1 1 d . . . . .
H7 H 0.390(6) 0.191(5) 0.590(4) 0.055(14) Uiso 1 1 d . . . . .
H4 H 0.122(6) 0.791(5) 0.413(4) 0.051(13) Uiso 1 1 d . . . . .


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 O1 1.9180(18) . ?
Cu1 O1 1.9180(18) 2_565 ?
Cu1 N4 2.022(2) 2_565 ?
Cu1 N4 2.022(2) . ?
Cu1 O2 2.354(2) . ?
Cu1 O2 2.354(2) 2_565 ?
O1 C3 1.279(3) . ?
O2 N6 1.243(3) . ?
O3 N6 1.215(3) . ?
O4 C5 1.316(3) . ?
O4 H4 0.82(4) . ?
O5 N7 1.238(3) . ?
O6 N7 1.251(3) . ?
O7 C7 1.325(3) . ?
O7 H7 0.77(4) . ?
O8 N8 1.216(3) . ?
O9 N8 1.231(3) . ?
N1 C1 1.326(4) . ?
N1 N2 1.330(3) . ?
N2 N3 1.309(3) . ?
N2 N5 1.394(4) . ?
N3 N4 1.324(3) . ?
N4 C1 1.353(3) . ?
N5 H5A 0.86(4) . ?
N5 H5B 0.90(4) . ?
N6 C4 1.447(4) . ?
N7 C6 1.413(4) . ?
N8 C8 1.462(4) . ?
C1 C2 1.479(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C8 1.409(4) . ?
C3 C4 1.420(4) . ?
C4 C5 1.403(4) . ?
C5 C6 1.427(4) . ?
C6 C7 1.422(4) . ?
C7 C8 1.369(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
O1 Cu1 O1 180.0 . 2_565 ?
O1 Cu1 N4 88.87(9) . 2_565 ?
O1 Cu1 N4 91.13(9) 2_565 2_565 ?
O1 Cu1 N4 91.13(9) . . ?
O1 Cu1 N4 88.87(9) 2_565 . ?
N4 Cu1 N4 180.0 2_565 . ?
O1 Cu1 O2 81.49(7) . . ?
O1 Cu1 O2 98.51(7) 2_565 . ?
N4 Cu1 O2 87.97(8) 2_565 . ?
N4 Cu1 O2 92.03(8) . . ?
O1 Cu1 O2 98.51(7) . 2_565 ?
O1 Cu1 O2 81.49(7) 2_565 2_565 ?
N4 Cu1 O2 92.03(8) 2_565 2_565 ?
N4 Cu1 O2 87.97(8) . 2_565 ?
O2 Cu1 O2 180.0 . 2_565 ?
C3 O1 Cu1 133.58(18) . . ?
N6 O2 Cu1 120.13(16) . . ?
C5 O4 H4 109(3) . . ?
C7 O7 H7 106(3) . . ?
C1 N1 N2 101.9(2) . . ?
N3 N2 N1 115.6(2) . . ?
N3 N2 N5 124.0(2) . . ?
N1 N2 N5 120.4(2) . . ?
N2 N3 N4 103.7(2) . . ?
N3 N4 C1 108.5(2) . . ?
N3 N4 Cu1 119.36(18) . . ?
C1 N4 Cu1 132.1(2) . . ?
N2 N5 H5A 107(2) . . ?
N2 N5 H5B 109(3) . . ?
H5A N5 H5B 115(3) . . ?
O3 N6 O2 122.3(2) . . ?
O3 N6 C4 119.8(2) . . ?
O2 N6 C4 117.8(2) . . ?
O5 N7 O6 119.8(2) . . ?
O5 N7 C6 120.5(3) . . ?
O6 N7 C6 119.7(3) . . ?
O8 N8 O9 124.5(3) . . ?
O8 N8 C8 117.7(2) . . ?
O9 N8 C8 117.7(2) . . ?
N1 C1 N4 110.3(3) . . ?
N1 C1 C2 123.8(3) . . ?
N4 C1 C2 125.9(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 C8 117.8(3) . . ?
O1 C3 C4 126.8(3) . . ?
C8 C3 C4 115.2(2) . . ?
C5 C4 C3 122.5(3) . . ?
C5 C4 N6 118.1(3) . . ?
C3 C4 N6 119.3(2) . . ?
O4 C5 C4 118.5(3) . . ?
O4 C5 C6 122.8(3) . . ?
C4 C5 C6 118.7(3) . . ?
N7 C6 C7 119.7(3) . . ?
N7 C6 C5 120.2(3) . . ?
C7 C6 C5 120.1(3) . . ?
O7 C7 C8 118.0(3) . . ?
O7 C7 C6 124.1(3) . . ?
C8 C7 C6 117.9(3) . . ?
C7 C8 C3 125.4(3) . . ?
C7 C8 N8 118.9(2) . . ?
C3 C8 N8 115.6(2) . . ?

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 N1 N2 N3 -1.6(3) . . . . ?
C1 N1 N2 N5 -179.5(3) . . . . ?
N1 N2 N3 N4 0.8(3) . . . . ?
N5 N2 N3 N4 178.7(2) . . . . ?
N2 N3 N4 C1 0.2(3) . . . . ?
N2 N3 N4 Cu1 178.36(16) . . . . ?
Cu1 O2 N6 O3 -125.1(2) . . . . ?
Cu1 O2 N6 C4 53.9(3) . . . . ?
N2 N1 C1 N4 1.6(3) . . . . ?
N2 N1 C1 C2 -178.2(3) . . . . ?
N3 N4 C1 N1 -1.2(3) . . . . ?
Cu1 N4 C1 N1 -179.01(19) . . . . ?
N3 N4 C1 C2 178.6(3) . . . . ?
Cu1 N4 C1 C2 0.8(4) . . . . ?
Cu1 O1 C3 C8 -157.7(2) . . . . ?
Cu1 O1 C3 C4 27.3(4) . . . . ?
O1 C3 C4 C5 179.8(3) . . . . ?
C8 C3 C4 C5 4.8(4) . . . . ?
O1 C3 C4 N6 -3.5(4) . . . . ?
C8 C3 C4 N6 -178.6(2) . . . . ?
O3 N6 C4 C5 -43.9(4) . . . . ?
O2 N6 C4 C5 137.0(3) . . . . ?
O3 N6 C4 C3 139.3(3) . . . . ?
O2 N6 C4 C3 -39.7(4) . . . . ?
C3 C4 C5 O4 174.9(3) . . . . ?
N6 C4 C5 O4 -1.8(4) . . . . ?
C3 C4 C5 C6 -3.5(4) . . . . ?
N6 C4 C5 C6 179.8(2) . . . . ?
O5 N7 C6 C7 178.9(3) . . . . ?
O6 N7 C6 C7 -2.8(4) . . . . ?
O5 N7 C6 C5 -0.9(4) . . . . ?
O6 N7 C6 C5 177.4(3) . . . . ?
O4 C5 C6 N7 1.3(4) . . . . ?
C4 C5 C6 N7 179.7(3) . . . . ?
O4 C5 C6 C7 -178.5(3) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
N7 C6 C7 O7 2.0(4) . . . . ?
C5 C6 C7 O7 -178.2(3) . . . . ?
N7 C6 C7 C8 -177.6(3) . . . . ?
C5 C6 C7 C8 2.2(4) . . . . ?
O7 C7 C8 C3 179.7(3) . . . . ?
C6 C7 C8 C3 -0.7(5) . . . . ?
O7 C7 C8 N8 2.4(4) . . . . ?
C6 C7 C8 N8 -178.0(3) . . . . ?
O1 C3 C8 C7 -178.2(3) . . . . ?
C4 C3 C8 C7 -2.7(4) . . . . ?
O1 C3 C8 N8 -0.8(4) . . . . ?
C4 C3 C8 N8 174.7(2) . . . . ?
O8 N8 C8 C7 68.7(4) . . . . ?
O9 N8 C8 C7 -112.0(3) . . . . ?
O8 N8 C8 C3 -108.8(3) . . . . ?
O9 N8 C8 C3 70.4(3) . . . . ?

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
C2 H2B O2 0.98 2.36 3.204(4) 143.5 .
C2 H2C O5 0.98 2.57 3.344(4) 135.4 1_554
N5 H5A O3 0.86(4) 2.42(4) 3.246(4) 163(3) 1_645
N5 H5B O9 0.90(4) 2.32(4) 3.208(4) 169(3) 2_655
O7 H7 O6 0.77(4) 1.84(4) 2.534(3) 150(4) .
O7 H7 O9 0.77(4) 2.46(4) 2.829(3) 111(4) 2_656
O7 H7 N7 0.77(4) 2.41(4) 2.869(3) 119(4) .
O4 H4 O5 0.82(4) 1.82(4) 2.544(3) 145(4) .
O4 H4 O8 0.82(4) 2.32(4) 2.899(3) 128(3) 1_565
O4 H4 N7 0.82(4) 2.41(4) 2.854(3) 115(3) .
C2 H2B O2 0.98 2.36 3.204(4) 143.5 .
C2 H2C O5 0.98 2.57 3.344(4) 135.4 1_554
N5 H5A O3 0.86(4) 2.42(4) 3.246(4) 163(3) 1_645
N5 H5B O9 0.90(4) 2.32(4) 3.208(4) 169(3) 2_655
O7 H7 O6 0.77(4) 1.84(4) 2.534(3) 150(4) .
O7 H7 O9 0.77(4) 2.46(4) 2.829(3) 111(4) 2_656
O7 H7 N7 0.77(4) 2.41(4) 2.869(3) 119(4) .
O4 H4 O5 0.82(4) 1.82(4) 2.544(3) 145(4) .
O4 H4 O8 0.82(4) 2.32(4) 2.899(3) 128(3) 1_565
O4 H4 N7 0.82(4) 2.41(4) 2.854(3) 115(3) .

_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.
;



_refine_diff_density_max         0.550
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.084

_shelxl_version_number           2013-4


####################################################################### 
# 
# 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_nx192
_database_code_depnum_ccdc_archive 'CCDC 1934810'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2018-05-24
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
1-amino-5-methyltetrazole
;
_chemical_name_common            1-amino-5-methyltetrazole
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H5 N5'
_chemical_formula_sum            'C2 H5 N5'
_chemical_formula_weight         99.11

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19
_symmetry_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7191(4)
_cell_length_b                   7.7483(5)
_cell_length_c                   10.4586(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     463.46(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1511
_cell_measurement_theta_min      4.6860
_cell_measurement_theta_max      31.3710

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88883
_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.
;

_exptl_special_details           ?


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_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            4787
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.429
_diffrn_reflns_theta_max         32.438
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1534
_reflns_number_gt                1360
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_max     0.887
_reflns_Friedel_fraction_full    1.000

_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    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Encifer 1.5.1, CCDC 2014'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 469 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_refine_ls_abs_structure_Flack   -0.1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1534
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000



_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
;



_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      -0.1213768000
_diffrn_orient_matrix_UB_12      0.0016440000
_diffrn_orient_matrix_UB_13      -0.0140435000
_diffrn_orient_matrix_UB_21      -0.0200347000
_diffrn_orient_matrix_UB_22      -0.0631980000
_diffrn_orient_matrix_UB_23      0.0477999000
_diffrn_orient_matrix_UB_31      -0.0161084000
_diffrn_orient_matrix_UB_32      0.0662215000
_diffrn_orient_matrix_UB_33      0.0459681000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00  95.20   0.80   10.00    --   29.79  77.00 120.00   64
  2  ω     55.00  99.00   0.80   10.00    --   29.79  57.00   0.00   55
  3  ω    -17.00  75.00   0.80   10.00    --   29.79 -99.00 -30.00  115
  4  ω     56.00 112.00   0.80   10.00    --   29.79-179.00 -90.00   70
  5  ω    -25.00  65.40   0.80   10.00    --   29.79 -99.00  90.00  113
  6  ω    -40.00  39.20   0.80   10.00    --   29.79 -57.00-150.00   99
  7  ω    -96.00 -72.00   0.80   10.00    --  -28.70 -57.00  90.00   30
;



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'
N N 0.0061 0.0033 '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_
_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 0.2344(2) 0.63243(14) 0.82067(11) 0.0246(3) Uani 1 1 d . . . . .
N2 N 0.0374(2) 0.54323(17) 0.84608(12) 0.0315(3) Uani 1 1 d . . . . .
N3 N -0.0272(3) 0.47807(17) 0.73757(13) 0.0369(3) Uani 1 1 d . . . . .
N4 N 0.1222(2) 0.52546(16) 0.64206(12) 0.0333(3) Uani 1 1 d . . . . .
N5 N 0.3603(2) 0.72228(19) 0.91293(12) 0.0308(3) Uani 1 1 d . . . . .
C1 C 0.2838(3) 0.62282(17) 0.69621(13) 0.0258(3) Uani 1 1 d . . . . .
C2 C 0.4807(3) 0.7128(2) 0.63356(16) 0.0377(4) Uani 1 1 d . . . . .
H5B H 0.283(4) 0.825(3) 0.9216(19) 0.051(6) Uiso 1 1 d . . . . .
H5A H 0.362(4) 0.667(3) 0.982(2) 0.053(6) Uiso 1 1 d . . . . .
H2A H 0.615(5) 0.697(3) 0.681(3) 0.072(7) Uiso 1 1 d . . . . .
H2C H 0.443(5) 0.827(3) 0.620(2) 0.058(7) Uiso 1 1 d . . . . .
H2B H 0.504(5) 0.660(3) 0.556(3) 0.066(7) Uiso 1 1 d . . . . .


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 C1 1.3341(18) . ?
N1 N2 1.3483(17) . ?
N1 N5 1.3910(16) . ?
N2 N3 1.2958(17) . ?
N3 N4 1.3647(19) . ?
N4 C1 1.3209(19) . ?
N5 H5B 0.91(2) . ?
N5 H5A 0.84(2) . ?
C1 C2 1.478(2) . ?
C2 H2A 0.92(3) . ?
C2 H2C 0.92(2) . ?
C2 H2B 0.92(3) . ?

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 N1 N2 109.94(12) . . ?
C1 N1 N5 126.51(12) . . ?
N2 N1 N5 123.54(11) . . ?
N3 N2 N1 105.38(12) . . ?
N2 N3 N4 110.96(13) . . ?
C1 N4 N3 106.14(12) . . ?
N1 N5 H5B 104.6(14) . . ?
N1 N5 H5A 110.2(15) . . ?
H5B N5 H5A 111.4(19) . . ?
N4 C1 N1 107.56(13) . . ?
N4 C1 C2 127.80(14) . . ?
N1 C1 C2 124.60(14) . . ?
C1 C2 H2A 109.5(16) . . ?
C1 C2 H2C 110.1(16) . . ?
H2A C2 H2C 114(2) . . ?
C1 C2 H2B 107.0(16) . . ?
H2A C2 H2B 107(2) . . ?
H2C C2 H2B 109(2) . . ?

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 N1 N2 N3 1.25(15) . . . . ?
N5 N1 N2 N3 -179.83(13) . . . . ?
N1 N2 N3 N4 -0.91(17) . . . . ?
N2 N3 N4 C1 0.25(18) . . . . ?
N3 N4 C1 N1 0.53(16) . . . . ?
N3 N4 C1 C2 -177.20(15) . . . . ?
N2 N1 C1 N4 -1.12(15) . . . . ?
N5 N1 C1 N4 180.00(13) . . . . ?
N2 N1 C1 C2 176.71(14) . . . . ?
N5 N1 C1 C2 -2.2(2) . . . . ?

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
N5 H5B N3 0.91(2) 2.51(2) 3.168(2) 128.9(16) 4_556




_refine_diff_density_max         0.134
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037

_shelxl_version_number           ?


####################################################################### 
# 
# 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_xv324
_database_code_depnum_ccdc_archive 'CCDC 1934813'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             ?
_audit_creation_method           SHELXL-2018/3


_chemical_name_systematic        'insert here'
_chemical_name_common            
'copper(II) 1-AMT trinitrophloroglucinate hydrate'
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 Cu N13 O11, C6 H2 N3 O9'
_chemical_formula_sum            'C16 H18 Cu N16 O20'
_chemical_formula_weight         818.00

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14
_symmetry_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                   19.3734(7)
_cell_length_b                   7.3825(3)
_cell_length_c                   20.6095(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.8360(10)
_cell_angle_gamma                90
_cell_volume                     2789.80(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    111(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.9502
_cell_measurement_theta_max      26.3761

_exptl_crystal_description       rod
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.909
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.7031
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_exptl_special_details           ?


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.948
_exptl_crystal_F_000             1660
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      111(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode generator'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'mix of omega and phi scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            44649
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.950
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5708
_reflns_number_gt                4968
_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       'Bruker Instrument Service v3.0.21'
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'enCIFer 1.5.1 (CCDC 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0307P)²+3.1777P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5708
_refine_ls_number_parameters     528
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0726
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000



_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
;



_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?

_diffrn_detector                 ?
_diffrn_detector_type            ?



_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?
_diffrn_measurement_details      ?



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_
_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 0.50692(2) 0.48409(3) 0.18791(2) 0.01075(8) Uani 1 1 d . . . . .
O1 O 0.39977(7) 0.4389(2) 0.15767(7) 0.0126(3) Uani 1 1 d . . . . .
O2 O 0.45781(8) 0.6426(2) 0.07714(7) 0.0157(3) Uani 1 1 d . . . . .
O3 O 0.42305(8) 0.5459(2) -0.02771(8) 0.0226(4) Uani 1 1 d . . . . .
O4 O 0.28547(9) 0.5609(2) -0.08094(8) 0.0182(3) Uani 1 1 d . . . . .
O5 O 0.15317(9) 0.4881(2) -0.12872(8) 0.0222(4) Uani 1 1 d . . . . .
O6 O 0.09676(8) 0.3525(2) -0.06768(8) 0.0240(4) Uani 1 1 d . . . . .
O7 O 0.15356(9) 0.3164(2) 0.06215(9) 0.0206(4) Uani 1 1 d . . . . .
O8 O 0.24459(10) 0.4385(2) 0.20211(8) 0.0281(4) Uani 1 1 d . . . . .
O9 O 0.30094(12) 0.1914(3) 0.19793(10) 0.0403(5) Uani 1 1 d . . . . .
O10 O 0.55460(9) 0.3572(2) 0.28678(8) 0.0168(3) Uani 1 1 d . . . . .
O11 O 0.61035(8) 0.5690(2) 0.19348(8) 0.0141(3) Uani 1 1 d . . . . .
N1 N 0.45855(9) 0.9121(2) 0.29089(9) 0.0134(4) Uani 1 1 d . . . . .
N2 N 0.50170(10) 0.9901(2) 0.25928(9) 0.0146(4) Uani 1 1 d . . . . .
N3 N 0.52147(9) 0.8646(2) 0.22592(9) 0.0136(4) Uani 1 1 d . . . . .
N4 N 0.49054(9) 0.7050(2) 0.23529(8) 0.0111(3) Uani 1 1 d . . . . .
N5 N 0.42839(13) 1.0162(3) 0.33118(12) 0.0263(5) Uani 1 1 d . . . . .
N6 N 0.55471(9) 0.0206(2) 0.10131(8) 0.0112(3) Uani 1 1 d . . . . .
N7 N 0.48602(9) 0.0569(2) 0.06138(9) 0.0127(4) Uani 1 1 d . . . . .
N8 N 0.46719(9) 0.2037(2) 0.08480(9) 0.0129(4) Uani 1 1 d . . . . .
N9 N 0.52314(9) 0.2639(2) 0.13942(8) 0.0115(3) Uani 1 1 d . . . . .
N10 N 0.59045(10) -0.1410(2) 0.09471(9) 0.0129(4) Uani 1 1 d . . . . .
N11 N 0.41260(9) 0.5658(2) 0.02739(9) 0.0133(4) Uani 1 1 d . . . . .
N12 N 0.15305(10) 0.4246(3) -0.07235(9) 0.0165(4) Uani 1 1 d . . . . .
N13 N 0.27331(9) 0.3338(2) 0.17328(9) 0.0138(4) Uani 1 1 d . . . . .
C1 C 0.45154(11) 0.7360(3) 0.27638(10) 0.0122(4) Uani 1 1 d . . . . .
C2 C 0.40954(11) 0.6070(3) 0.30412(11) 0.0146(4) Uani 1 1 d . . . . .
H2A H 0.414422 0.484639 0.287712 0.022 Uiso 1 1 calc R U . . .
H2B H 0.357996 0.642138 0.288654 0.022 Uiso 1 1 calc R U . . .
H2C H 0.428428 0.609018 0.354327 0.022 Uiso 1 1 calc R U . . .
C3 C 0.57774(11) 0.1472(3) 0.14976(10) 0.0123(4) Uani 1 1 d . . . . .
C4 C 0.65077(11) 0.1498(3) 0.20289(11) 0.0174(5) Uani 1 1 d . . . . .
H4A H 0.683771 0.226019 0.187350 0.026 Uiso 1 1 calc R U . . .
H4B H 0.670148 0.026178 0.210752 0.026 Uiso 1 1 calc R U . . .
H4C H 0.646642 0.198798 0.245676 0.026 Uiso 1 1 calc R U . . .
C5 C 0.34613(11) 0.4428(3) 0.10303(10) 0.0107(4) Uani 1 1 d . . . . .
C6 C 0.34601(11) 0.5010(3) 0.03618(10) 0.0121(4) Uani 1 1 d . . . . .
C7 C 0.28291(11) 0.4986(3) -0.02158(10) 0.0130(4) Uani 1 1 d . . . . .
C8 C 0.21620(11) 0.4333(3) -0.01456(11) 0.0134(4) Uani 1 1 d . . . . .
C9 C 0.21354(11) 0.3764(3) 0.05080(11) 0.0137(4) Uani 1 1 d . . . . .
C10 C 0.27675(11) 0.3851(3) 0.10540(10) 0.0124(4) Uani 1 1 d . . . . .
O12 O 0.32342(8) 0.9858(2) -0.00167(8) 0.0182(3) Uani 1 1 d . . . . .
O13 O 0.23755(9) 1.1281(2) -0.12672(8) 0.0210(4) Uani 1 1 d . . . . .
O14 O 0.18833(8) 0.8700(2) -0.16631(7) 0.0181(3) Uani 1 1 d . . . . .
O15 O 0.07204(8) 0.9007(2) -0.11092(7) 0.0160(3) Uani 1 1 d . . . . .
O16 O 0.01287(9) 0.6791(2) -0.03208(9) 0.0294(4) Uani 1 1 d . . . . .
O17 O 0.02572(9) 0.8606(3) 0.05274(9) 0.0336(5) Uani 1 1 d . . . . .
O18 O 0.16712(9) 0.7838(2) 0.12554(8) 0.0182(3) Uani 1 1 d . . . . .
O19 O 0.30361(8) 0.8116(2) 0.17936(7) 0.0180(3) Uani 1 1 d . . . . .
O20 O 0.37117(8) 0.9245(2) 0.12421(8) 0.0184(3) Uani 1 1 d . . . . .
N14 N 0.20897(9) 0.9842(3) -0.12033(9) 0.0144(4) Uani 1 1 d . . . . .
N15 N 0.04818(9) 0.7891(3) 0.01003(9) 0.0165(4) Uani 1 1 d . . . . .
N16 N 0.30985(9) 0.8742(2) 0.12524(9) 0.0130(4) Uani 1 1 d . . . . .
C11 C 0.25820(11) 0.9420(3) 0.00295(11) 0.0129(4) Uani 1 1 d . . . . .
C12 C 0.19853(11) 0.9413(3) -0.05527(10) 0.0127(4) Uani 1 1 d . . . . .
C13 C 0.12546(11) 0.8914(3) -0.05769(11) 0.0131(4) Uani 1 1 d . . . . .
C14 C 0.12010(11) 0.8388(3) 0.00774(11) 0.0129(4) Uani 1 1 d . . . . .
C15 C 0.17810(11) 0.8358(3) 0.06819(10) 0.0123(4) Uani 1 1 d . . . . .
C16 C 0.24897(11) 0.8871(3) 0.06619(10) 0.0122(4) Uani 1 1 d . . . . .
H5B H 0.3850(18) 1.035(4) 0.3128(15) 0.032(8) Uiso 1 1 d . . . . .
H11A H 0.6366(16) 0.588(4) 0.2349(16) 0.033(8) Uiso 1 1 d . . . . .
H10A H 0.6182(15) -0.116(4) 0.0718(14) 0.026(7) Uiso 1 1 d . . . . .
H10B H 0.5549(15) -0.209(4) 0.0678(13) 0.022(7) Uiso 1 1 d . . . . .
H11B H 0.6123(17) 0.667(5) 0.1693(16) 0.042(9) Uiso 1 1 d . . . . .
H5A H 0.453(2) 1.008(5) 0.373(2) 0.058(11) Uiso 1 1 d . . . . .
H10D H 0.5584(17) 0.412(5) 0.3230(17) 0.043(9) Uiso 1 1 d . . . . .
H10C H 0.5384(18) 0.262(5) 0.2915(17) 0.045(10) Uiso 1 1 d . . . . .
H18A H 0.2066(17) 0.786(4) 0.1537(15) 0.035(9) Uiso 1 1 d . . . . .
H7A H 0.1224(18) 0.309(4) 0.0265(17) 0.041(9) Uiso 1 1 d . . . . .
H4D H 0.2414(18) 0.558(4) -0.1087(17) 0.044(9) Uiso 1 1 d . . . . .
H12A H 0.3516(18) 0.988(4) 0.0340(17) 0.043(10) Uiso 1 1 d . . . . .


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 1.9785(17) . ?
Cu1 N9 1.9858(17) . ?
Cu1 O1 1.9934(14) . ?
Cu1 O11 2.0673(15) . ?
Cu1 O10 2.1604(16) . ?
O1 C5 1.262(2) . ?
O2 N11 1.249(2) . ?
O3 N11 1.225(2) . ?
O4 C7 1.323(3) . ?
O4 H4D 0.86(3) . ?
O5 N12 1.253(2) . ?
O6 N12 1.245(2) . ?
O7 C9 1.333(3) . ?
O7 H7A 0.79(3) . ?
O8 N13 1.214(2) . ?
O9 N13 1.215(2) . ?
O10 H10D 0.83(3) . ?
O10 H10C 0.79(4) . ?
O11 H11A 0.85(3) . ?
O11 H11B 0.88(3) . ?
N1 C1 1.331(3) . ?
N1 N2 1.344(2) . ?
N1 N5 1.391(3) . ?
N2 N3 1.284(3) . ?
N3 N4 1.363(2) . ?
N4 C1 1.324(3) . ?
N5 H5B 0.81(3) . ?
N5 H5A 0.85(4) . ?
N6 C3 1.335(3) . ?
N6 N7 1.346(2) . ?
N6 N10 1.408(2) . ?
N7 N8 1.287(2) . ?
N8 N9 1.361(2) . ?
N9 C3 1.327(3) . ?
N10 H10A 0.84(3) . ?
N10 H10B 0.89(3) . ?
N11 C6 1.441(3) . ?
N12 C8 1.407(3) . ?
N13 C10 1.471(3) . ?
C1 C2 1.482(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.484(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.426(3) . ?
C5 C6 1.442(3) . ?
C6 C7 1.404(3) . ?
C7 C8 1.430(3) . ?
C8 C9 1.428(3) . ?
C9 C10 1.371(3) . ?
O12 C11 1.337(3) . ?
O12 H12A 0.76(3) . ?
O13 N14 1.225(2) . ?
O14 N14 1.234(2) . ?
O15 C13 1.243(3) . ?
O16 N15 1.224(2) . ?
O17 N15 1.221(2) . ?
O18 C15 1.324(2) . ?
O18 H18A 0.80(3) . ?
O19 N16 1.249(2) . ?
O20 N16 1.251(2) . ?
N14 C12 1.454(3) . ?
N15 C14 1.456(3) . ?
N16 C16 1.398(3) . ?
C11 C12 1.371(3) . ?
C11 C16 1.430(3) . ?
C12 C13 1.448(3) . ?
C13 C14 1.439(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.438(3) . ?

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 N9 179.38(7) . . ?
N4 Cu1 O1 88.60(6) . . ?
N9 Cu1 O1 91.35(6) . . ?
N4 Cu1 O11 91.70(7) . . ?
N9 Cu1 O11 88.18(6) . . ?
O1 Cu1 O11 163.97(6) . . ?
N4 Cu1 O10 88.83(7) . . ?
N9 Cu1 O10 91.77(7) . . ?
O1 Cu1 O10 107.90(6) . . ?
O11 Cu1 O10 88.14(6) . . ?
C5 O1 Cu1 138.53(13) . . ?
C7 O4 H4D 106(2) . . ?
C9 O7 H7A 108(2) . . ?
Cu1 O10 H10D 121(2) . . ?
Cu1 O10 H10C 116(2) . . ?
H10D O10 H10C 104(3) . . ?
Cu1 O11 H11A 111.1(19) . . ?
Cu1 O11 H11B 116(2) . . ?
H11A O11 H11B 108(3) . . ?
C1 N1 N2 110.11(17) . . ?
C1 N1 N5 129.9(2) . . ?
N2 N1 N5 119.98(18) . . ?
N3 N2 N1 106.86(16) . . ?
N2 N3 N4 109.09(16) . . ?
C1 N4 N3 107.98(17) . . ?
C1 N4 Cu1 132.37(15) . . ?
N3 N4 Cu1 119.63(12) . . ?
N1 N5 H5B 113(2) . . ?
N1 N5 H5A 112(2) . . ?
H5B N5 H5A 130(3) . . ?
C3 N6 N7 110.10(17) . . ?
C3 N6 N10 127.56(17) . . ?
N7 N6 N10 121.95(16) . . ?
N8 N7 N6 106.38(16) . . ?
N7 N8 N9 109.80(16) . . ?
C3 N9 N8 107.57(17) . . ?
C3 N9 Cu1 134.27(14) . . ?
N8 N9 Cu1 118.05(13) . . ?
N6 N10 H10A 106.8(19) . . ?
N6 N10 H10B 103.6(17) . . ?
H10A N10 H10B 107(2) . . ?
O3 N11 O2 122.25(17) . . ?
O3 N11 C6 119.94(17) . . ?
O2 N11 C6 117.80(16) . . ?
O6 N12 O5 119.70(18) . . ?
O6 N12 C8 119.88(18) . . ?
O5 N12 C8 120.42(18) . . ?
O8 N13 O9 123.80(19) . . ?
O8 N13 C10 118.04(18) . . ?
O9 N13 C10 118.13(18) . . ?
N4 C1 N1 105.95(18) . . ?
N4 C1 C2 129.28(19) . . ?
N1 C1 C2 124.75(19) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N9 C3 N6 106.13(17) . . ?
N9 C3 C4 129.14(19) . . ?
N6 C3 C4 124.73(19) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 C10 118.44(18) . . ?
O1 C5 C6 127.31(18) . . ?
C10 C5 C6 114.26(18) . . ?
C7 C6 N11 117.84(18) . . ?
C7 C6 C5 122.59(18) . . ?
N11 C6 C5 119.56(18) . . ?
O4 C7 C6 119.83(19) . . ?
O4 C7 C8 121.05(19) . . ?
C6 C7 C8 119.09(18) . . ?
N12 C8 C9 119.93(18) . . ?
N12 C8 C7 119.82(19) . . ?
C9 C8 C7 120.26(18) . . ?
O7 C9 C10 118.01(19) . . ?
O7 C9 C8 124.22(19) . . ?
C10 C9 C8 117.76(18) . . ?
C9 C10 C5 126.00(19) . . ?
C9 C10 N13 117.75(18) . . ?
C5 C10 N13 116.24(17) . . ?
C11 O12 H12A 110(2) . . ?
C15 O18 H18A 105(2) . . ?
O13 N14 O14 123.73(18) . . ?
O13 N14 C12 119.36(17) . . ?
O14 N14 C12 116.91(17) . . ?
O17 N15 O16 123.41(19) . . ?
O17 N15 C14 118.82(18) . . ?
O16 N15 C14 117.76(18) . . ?
O19 N16 O20 119.42(17) . . ?
O19 N16 C16 120.32(17) . . ?
O20 N16 C16 120.26(17) . . ?
O12 C11 C12 119.18(19) . . ?
O12 C11 C16 122.18(19) . . ?
C12 C11 C16 118.56(18) . . ?
C11 C12 C13 124.73(19) . . ?
C11 C12 N14 118.49(18) . . ?
C13 C12 N14 116.69(17) . . ?
O15 C13 C14 123.40(19) . . ?
O15 C13 C12 122.84(19) . . ?
C14 C13 C12 113.70(18) . . ?
C15 C14 C13 124.42(19) . . ?
C15 C14 N15 118.32(18) . . ?
C13 C14 N15 117.24(18) . . ?
O18 C15 C14 119.42(19) . . ?
O18 C15 C16 122.16(19) . . ?
C14 C15 C16 118.41(18) . . ?
N16 C16 C11 119.59(18) . . ?
N16 C16 C15 120.16(18) . . ?
C11 C16 C15 120.16(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
C1 N1 N2 N3 -0.3(2) . . . . ?
N5 N1 N2 N3 -179.79(18) . . . . ?
N1 N2 N3 N4 0.6(2) . . . . ?
N2 N3 N4 C1 -0.7(2) . . . . ?
N2 N3 N4 Cu1 177.76(13) . . . . ?
C3 N6 N7 N8 0.2(2) . . . . ?
N10 N6 N7 N8 173.58(17) . . . . ?
N6 N7 N8 N9 0.3(2) . . . . ?
N7 N8 N9 C3 -0.7(2) . . . . ?
N7 N8 N9 Cu1 -177.47(12) . . . . ?
N3 N4 C1 N1 0.5(2) . . . . ?
Cu1 N4 C1 N1 -177.68(14) . . . . ?
N3 N4 C1 C2 -177.70(19) . . . . ?
Cu1 N4 C1 C2 4.1(3) . . . . ?
N2 N1 C1 N4 -0.2(2) . . . . ?
N5 N1 C1 N4 179.3(2) . . . . ?
N2 N1 C1 C2 178.15(18) . . . . ?
N5 N1 C1 C2 -2.4(3) . . . . ?
N8 N9 C3 N6 0.7(2) . . . . ?
Cu1 N9 C3 N6 176.81(14) . . . . ?
N8 N9 C3 C4 -179.6(2) . . . . ?
Cu1 N9 C3 C4 -3.6(3) . . . . ?
N7 N6 C3 N9 -0.6(2) . . . . ?
N10 N6 C3 N9 -173.52(18) . . . . ?
N7 N6 C3 C4 179.78(19) . . . . ?
N10 N6 C3 C4 6.8(3) . . . . ?
Cu1 O1 C5 C10 175.58(14) . . . . ?
Cu1 O1 C5 C6 -4.7(3) . . . . ?
O3 N11 C6 C7 -30.3(3) . . . . ?
O2 N11 C6 C7 149.13(19) . . . . ?
O3 N11 C6 C5 150.2(2) . . . . ?
O2 N11 C6 C5 -30.4(3) . . . . ?
O1 C5 C6 C7 179.6(2) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
O1 C5 C6 N11 -0.9(3) . . . . ?
C10 C5 C6 N11 178.81(18) . . . . ?
N11 C6 C7 O4 -2.4(3) . . . . ?
C5 C6 C7 O4 177.12(19) . . . . ?
N11 C6 C7 C8 179.38(18) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
O6 N12 C8 C9 -6.4(3) . . . . ?
O5 N12 C8 C9 174.03(19) . . . . ?
O6 N12 C8 C7 173.39(19) . . . . ?
O5 N12 C8 C7 -6.2(3) . . . . ?
O4 C7 C8 N12 3.8(3) . . . . ?
C6 C7 C8 N12 -177.96(19) . . . . ?
O4 C7 C8 C9 -176.39(19) . . . . ?
C6 C7 C8 C9 1.8(3) . . . . ?
N12 C8 C9 O7 -1.2(3) . . . . ?
C7 C8 C9 O7 179.0(2) . . . . ?
N12 C8 C9 C10 179.13(19) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
O7 C9 C10 C5 179.0(2) . . . . ?
C8 C9 C10 C5 -1.4(3) . . . . ?
O7 C9 C10 N13 -2.2(3) . . . . ?
C8 C9 C10 N13 177.45(18) . . . . ?
O1 C5 C10 C9 -178.2(2) . . . . ?
C6 C5 C10 C9 2.0(3) . . . . ?
O1 C5 C10 N13 3.0(3) . . . . ?
C6 C5 C10 N13 -176.83(17) . . . . ?
O8 N13 C10 C9 -73.9(3) . . . . ?
O9 N13 C10 C9 107.9(2) . . . . ?
O8 N13 C10 C5 105.0(2) . . . . ?
O9 N13 C10 C5 -73.2(3) . . . . ?
O12 C11 C12 C13 178.1(2) . . . . ?
C16 C11 C12 C13 1.1(3) . . . . ?
O12 C11 C12 N14 1.5(3) . . . . ?
C16 C11 C12 N14 -175.48(18) . . . . ?
O13 N14 C12 C11 -56.2(3) . . . . ?
O14 N14 C12 C11 123.4(2) . . . . ?
O13 N14 C12 C13 126.9(2) . . . . ?
O14 N14 C12 C13 -53.5(3) . . . . ?
C11 C12 C13 O15 176.5(2) . . . . ?
N14 C12 C13 O15 -6.9(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
N14 C12 C13 C14 175.94(18) . . . . ?
O15 C13 C14 C15 -176.8(2) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
O15 C13 C14 N15 1.9(3) . . . . ?
C12 C13 C14 N15 179.08(18) . . . . ?
O17 N15 C14 C15 49.9(3) . . . . ?
O16 N15 C14 C15 -131.2(2) . . . . ?
O17 N15 C14 C13 -128.8(2) . . . . ?
O16 N15 C14 C13 50.0(3) . . . . ?
C13 C14 C15 O18 -179.5(2) . . . . ?
N15 C14 C15 O18 1.8(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
N15 C14 C15 C16 -179.21(18) . . . . ?
O19 N16 C16 C11 -173.80(19) . . . . ?
O20 N16 C16 C11 5.8(3) . . . . ?
O19 N16 C16 C15 2.8(3) . . . . ?
O20 N16 C16 C15 -177.60(18) . . . . ?
O12 C11 C16 N16 -1.4(3) . . . . ?
C12 C11 C16 N16 175.46(19) . . . . ?
O12 C11 C16 C15 -178.04(19) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?
O18 C15 C16 N16 3.3(3) . . . . ?
C14 C15 C16 N16 -175.70(19) . . . . ?
O18 C15 C16 C11 179.87(19) . . . . ?
C14 C15 C16 C11 0.9(3) . . . . ?

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
C2 H2A O1 0.98 2.62 3.212(3) 118.7 .




_refine_diff_density_max         0.397
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.063

_shelxl_version_number           ?


####################################################################### 
# 
# 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_mx174
_database_code_depnum_ccdc_archive 'CCDC 1934812'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             
;
'Wed Apr 12 16:27:45 2017'
;
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
tetrakis(2-aminotetrazolyl) bis(phloroglucinato) copper(II)
;
_chemical_name_common            
'tetrakis(2-aminotetrazolyl) bis(phloroglucinato) copper(II)'
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Cu N26 O18'
_chemical_formula_sum            'C16 H16 Cu N26 O18'
_chemical_formula_weight         924.09

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_symmetry_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                   8.6130(7)
_cell_length_b                   9.2780(9)
_cell_length_c                   11.6430(12)
_cell_angle_alpha                106.515(9)
_cell_angle_beta                 101.929(7)
_cell_angle_gamma                107.829(8)
_cell_volume                     804.01(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1984
_cell_measurement_theta_min      4.5950
_cell_measurement_theta_max      30.6410

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.805
_shelx_estimated_absorpt_T_min   0.818
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98572
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_F_000             467
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            6244
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.261
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.240
_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             3143
_reflns_number_gt                2592
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'enCIFer 1.5.1 (CCDC 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.0636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3143
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      -0.0214060000
_diffrn_orient_matrix_UB_12      -0.0359298000
_diffrn_orient_matrix_UB_13      0.0438021000
_diffrn_orient_matrix_UB_21      -0.0885979000
_diffrn_orient_matrix_UB_22      -0.0312509000
_diffrn_orient_matrix_UB_23      -0.0354794000
_diffrn_orient_matrix_UB_31      0.0063789000
_diffrn_orient_matrix_UB_32      -0.0722802000
_diffrn_orient_matrix_UB_33      -0.0364219000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -82.00   47.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994   19.0000 -150.0000 129

#__ type_ start__ end____ width___ exp.time_
  2 omega  -98.00  -47.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
  3 omega -101.00  -24.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  -77.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
  4 omega -109.00  -45.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
  5 omega -109.00  -69.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega   25.00   73.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   65.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega  -21.00   12.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000  -90.0000 33

;



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_
_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 0.5000 0.5000 0.0000 0.01863(13) Uani 1 2 d S . P . .
O1 O 0.4266(2) 0.4423(2) 0.17113(16) 0.0247(4) Uani 1 1 d . . . . .
O2 O 0.5504(3) 0.7386(2) 0.37294(19) 0.0368(5) Uani 1 1 d . . . . .
O3 O 0.8215(3) 0.7815(2) 0.43321(18) 0.0363(5) Uani 1 1 d . . . . .
O4 O 0.8182(3) 0.5977(2) 0.57449(18) 0.0364(5) Uani 1 1 d . . . . .
H4 H 0.8609 0.5570 0.6222 0.055 Uiso 1 1 calc R U . . .
O5 O 0.8481(3) 0.3687(2) 0.64325(18) 0.0392(5) Uani 1 1 d . . . . .
O6 O 0.6994(3) 0.1159(2) 0.52413(18) 0.0364(5) Uani 1 1 d . . . . .
O7 O 0.4863(2) 0.02895(19) 0.31046(17) 0.0259(4) Uani 1 1 d . . . . .
H7 H 0.5420 0.0155 0.3721 0.039 Uiso 1 1 calc R U . . .
O8 O 0.3785(2) 0.0047(2) 0.06755(16) 0.0272(4) Uani 1 1 d . . . . .
O9 O 0.1957(2) 0.1180(2) 0.08265(17) 0.0312(5) Uani 1 1 d . . . . .
N1 N 0.1780(3) 0.0143(2) -0.2222(2) 0.0259(5) Uani 1 1 d . . . . .
N2 N 0.0799(3) 0.0994(2) -0.23113(19) 0.0200(5) Uani 1 1 d . . . . .
N3 N 0.1574(3) 0.2558(2) -0.17113(19) 0.0212(5) Uani 1 1 d . . . . .
N4 N 0.3212(3) 0.2794(2) -0.11626(18) 0.0188(4) Uani 1 1 d . . . . .
N5 N -0.0943(3) 0.0232(3) -0.2957(3) 0.0318(6) Uani 1 1 d . . . . .
N6 N 0.8781(3) 0.3159(3) -0.0427(2) 0.0253(5) Uani 1 1 d . . . . .
N7 N 0.8704(2) 0.3280(2) 0.07229(19) 0.0193(5) Uani 1 1 d . . . . .
N8 N 0.7553(3) 0.3793(2) 0.10470(19) 0.0205(5) Uani 1 1 d . . . . .
N9 N 0.6799(2) 0.4038(2) 0.00408(18) 0.0186(4) Uani 1 1 d . . . . .
N10 N 0.9790(3) 0.2918(3) 0.1562(2) 0.0279(5) Uani 1 1 d . . . . .
N11 N 0.6680(3) 0.6914(3) 0.3956(2) 0.0266(5) Uani 1 1 d . . . . .
N12 N 0.7395(3) 0.2643(3) 0.5416(2) 0.0288(5) Uani 1 1 d . . . . .
N13 N 0.3351(3) 0.1115(2) 0.12493(19) 0.0204(5) Uani 1 1 d . . . . .
C1 C 0.3286(3) 0.1317(3) -0.1501(2) 0.0235(6) Uani 1 1 d . . . . .
H1 H 0.4310 0.1136 -0.1251 0.028 Uiso 1 1 calc R U . . .
C2 C 0.7564(3) 0.3659(3) -0.0827(2) 0.0227(6) Uani 1 1 d . . . . .
H2 H 0.7268 0.3740 -0.1632 0.027 Uiso 1 1 calc R U . . .
C3 C 0.4936(3) 0.4034(3) 0.2577(2) 0.0197(5) Uani 1 1 d . . . . .
C4 C 0.6219(3) 0.5194(3) 0.3754(2) 0.0214(5) Uani 1 1 d . . . . .
C5 C 0.7056(3) 0.4791(3) 0.4680(2) 0.0241(6) Uani 1 1 d . . . . .
C6 C 0.6616(3) 0.3096(3) 0.4477(2) 0.0237(6) Uani 1 1 d . . . . .
C7 C 0.5350(3) 0.1878(3) 0.3331(2) 0.0198(5) Uani 1 1 d . . . . .
C8 C 0.4557(3) 0.2361(3) 0.2443(2) 0.0183(5) Uani 1 1 d . . . . .
H5A H -0.128(4) 0.097(4) -0.307(3) 0.035(8) Uiso 1 1 d . . . . .
H5B H -0.106(4) -0.042(4) -0.370(3) 0.042(10) Uiso 1 1 d . . . . .
H10B H 1.053(4) 0.276(4) 0.126(3) 0.048(10) Uiso 1 1 d . . . . .
H10A H 0.909(5) 0.200(5) 0.166(4) 0.070(12) Uiso 1 1 d . . . . .


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 2.006(2) 2_665 ?
Cu1 N4 2.006(2) . ?
Cu1 N9 2.0101(17) . ?
Cu1 N9 2.0101(17) 2_665 ?
Cu1 O1 2.3614(17) 2_665 ?
Cu1 O1 2.3614(17) . ?
O1 C3 1.254(3) . ?
O2 N11 1.230(3) . ?
O3 N11 1.231(3) . ?
O4 C5 1.328(3) . ?
O4 H4 0.8400 . ?
O5 N12 1.245(3) . ?
O6 N12 1.256(3) . ?
O7 C7 1.331(3) . ?
O7 H7 0.8400 . ?
O8 N13 1.234(2) . ?
O9 N13 1.227(2) . ?
N1 C1 1.318(3) . ?
N1 N2 1.330(3) . ?
N2 N3 1.295(3) . ?
N2 N5 1.378(3) . ?
N3 N4 1.343(3) . ?
N4 C1 1.340(3) . ?
N5 H5A 0.85(3) . ?
N5 H5B 0.86(3) . ?
N6 C2 1.323(3) . ?
N6 N7 1.329(3) . ?
N7 N8 1.302(3) . ?
N7 N10 1.394(3) . ?
N8 N9 1.331(3) . ?
N9 C2 1.339(3) . ?
N10 H10B 0.82(3) . ?
N10 H10A 0.93(4) . ?
N11 C4 1.456(3) . ?
N12 C6 1.397(3) . ?
N13 C8 1.449(3) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.437(3) . ?
C3 C8 1.439(3) . ?
C4 C5 1.376(3) . ?
C5 C6 1.435(3) . ?
C6 C7 1.426(3) . ?
C7 C8 1.378(3) . ?

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 N4 180.0 2_665 . ?
N4 Cu1 N9 90.83(7) 2_665 . ?
N4 Cu1 N9 89.17(7) . . ?
N4 Cu1 N9 89.17(7) 2_665 2_665 ?
N4 Cu1 N9 90.83(7) . 2_665 ?
N9 Cu1 N9 180.0 . 2_665 ?
N4 Cu1 O1 88.37(7) 2_665 2_665 ?
N4 Cu1 O1 91.62(7) . 2_665 ?
N9 Cu1 O1 84.62(7) . 2_665 ?
N9 Cu1 O1 95.38(7) 2_665 2_665 ?
N4 Cu1 O1 91.62(7) 2_665 . ?
N4 Cu1 O1 88.38(7) . . ?
N9 Cu1 O1 95.38(7) . . ?
N9 Cu1 O1 84.62(7) 2_665 . ?
O1 Cu1 O1 180.0 2_665 . ?
C3 O1 Cu1 135.50(15) . . ?
C5 O4 H4 109.5 . . ?
C7 O7 H7 109.5 . . ?
C1 N1 N2 101.07(19) . . ?
N3 N2 N1 115.6(2) . . ?
N3 N2 N5 122.9(2) . . ?
N1 N2 N5 121.3(2) . . ?
N2 N3 N4 104.51(17) . . ?
C1 N4 N3 106.31(19) . . ?
C1 N4 Cu1 131.16(16) . . ?
N3 N4 Cu1 122.43(14) . . ?
N2 N5 H5A 106(2) . . ?
N2 N5 H5B 107(2) . . ?
H5A N5 H5B 107(3) . . ?
C2 N6 N7 100.95(19) . . ?
N8 N7 N6 115.86(18) . . ?
N8 N7 N10 120.7(2) . . ?
N6 N7 N10 123.4(2) . . ?
N7 N8 N9 103.96(19) . . ?
N8 N9 C2 107.38(17) . . ?
N8 N9 Cu1 123.27(15) . . ?
C2 N9 Cu1 129.14(16) . . ?
N7 N10 H10B 108(2) . . ?
N7 N10 H10A 106(2) . . ?
H10B N10 H10A 113(3) . . ?
O2 N11 O3 123.4(2) . . ?
O2 N11 C4 117.9(2) . . ?
O3 N11 C4 118.6(2) . . ?
O5 N12 O6 119.0(2) . . ?
O5 N12 C6 121.2(2) . . ?
O6 N12 C6 119.8(2) . . ?
O9 N13 O8 122.2(2) . . ?
O9 N13 C8 119.19(18) . . ?
O8 N13 C8 118.58(18) . . ?
N1 C1 N4 112.5(2) . . ?
N1 C1 H1 123.8 . . ?
N4 C1 H1 123.8 . . ?
N6 C2 N9 111.8(2) . . ?
N6 C2 H2 124.1 . . ?
N9 C2 H2 124.1 . . ?
O1 C3 C4 123.7(2) . . ?
O1 C3 C8 122.4(2) . . ?
C4 C3 C8 113.7(2) . . ?
C5 C4 C3 124.7(2) . . ?
C5 C4 N11 118.3(2) . . ?
C3 C4 N11 117.0(2) . . ?
O4 C5 C4 119.1(2) . . ?
O4 C5 C6 122.5(2) . . ?
C4 C5 C6 118.4(2) . . ?
N12 C6 C7 120.1(2) . . ?
N12 C6 C5 120.0(2) . . ?
C7 C6 C5 119.9(2) . . ?
O7 C7 C8 118.6(2) . . ?
O7 C7 C6 122.5(2) . . ?
C8 C7 C6 118.8(2) . . ?
C7 C8 C3 124.4(2) . . ?
C7 C8 N13 118.3(2) . . ?
C3 C8 N13 117.1(2) . . ?

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 N1 N2 N3 -0.2(3) . . . . ?
C1 N1 N2 N5 -177.4(2) . . . . ?
N1 N2 N3 N4 -0.4(3) . . . . ?
N5 N2 N3 N4 176.8(2) . . . . ?
N2 N3 N4 C1 0.8(2) . . . . ?
N2 N3 N4 Cu1 -175.88(15) . . . . ?
C2 N6 N7 N8 0.4(3) . . . . ?
C2 N6 N7 N10 -178.5(2) . . . . ?
N6 N7 N8 N9 -0.1(3) . . . . ?
N10 N7 N8 N9 178.9(2) . . . . ?
N7 N8 N9 C2 -0.3(2) . . . . ?
N7 N8 N9 Cu1 -175.39(15) . . . . ?
N2 N1 C1 N4 0.7(3) . . . . ?
N3 N4 C1 N1 -1.0(3) . . . . ?
Cu1 N4 C1 N1 175.26(17) . . . . ?
N7 N6 C2 N9 -0.6(3) . . . . ?
N8 N9 C2 N6 0.6(3) . . . . ?
Cu1 N9 C2 N6 175.30(16) . . . . ?
Cu1 O1 C3 C4 84.9(3) . . . . ?
Cu1 O1 C3 C8 -91.2(3) . . . . ?
O1 C3 C4 C5 -175.4(2) . . . . ?
C8 C3 C4 C5 1.0(4) . . . . ?
O1 C3 C4 N11 3.3(4) . . . . ?
C8 C3 C4 N11 179.7(2) . . . . ?
O2 N11 C4 C5 -133.8(2) . . . . ?
O3 N11 C4 C5 46.8(3) . . . . ?
O2 N11 C4 C3 47.5(3) . . . . ?
O3 N11 C4 C3 -131.9(2) . . . . ?
C3 C4 C5 O4 -178.0(2) . . . . ?
N11 C4 C5 O4 3.3(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
N11 C4 C5 C6 -179.4(2) . . . . ?
O5 N12 C6 C7 -178.7(2) . . . . ?
O6 N12 C6 C7 0.9(4) . . . . ?
O5 N12 C6 C5 -0.4(4) . . . . ?
O6 N12 C6 C5 179.2(2) . . . . ?
O4 C5 C6 N12 -0.6(4) . . . . ?
C4 C5 C6 N12 -177.7(2) . . . . ?
O4 C5 C6 C7 177.7(2) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
N12 C6 C7 O7 -0.1(4) . . . . ?
C5 C6 C7 O7 -178.4(2) . . . . ?
N12 C6 C7 C8 177.6(2) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
O7 C7 C8 C3 178.8(2) . . . . ?
C6 C7 C8 C3 1.1(4) . . . . ?
O7 C7 C8 N13 -6.0(3) . . . . ?
C6 C7 C8 N13 176.2(2) . . . . ?
O1 C3 C8 C7 175.3(2) . . . . ?
C4 C3 C8 C7 -1.2(3) . . . . ?
O1 C3 C8 N13 0.1(3) . . . . ?
C4 C3 C8 N13 -176.40(19) . . . . ?
O9 N13 C8 C7 133.7(2) . . . . ?
O8 N13 C8 C7 -48.3(3) . . . . ?
O9 N13 C8 C3 -50.8(3) . . . . ?
O8 N13 C8 C3 127.2(2) . . . . ?

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
O4 H4 O5 0.84 1.81 2.537(3) 144.5 .
O4 H4 N12 0.84 2.40 2.847(3) 114.1 .
O4 H4 N10 0.84 2.41 2.957(3) 123.3 2_766
O7 H7 O6 0.84 1.77 2.505(2) 144.8 .
O7 H7 N12 0.84 2.39 2.843(3) 114.1 .
O7 H7 O2 0.84 2.60 3.154(2) 125.1 1_545
N5 H5A O6 0.85(3) 2.30(3) 2.952(3) 134(3) 1_454
N5 H5B O3 0.86(3) 2.23(3) 3.090(4) 171(3) 1_444
N10 H10B O9 0.82(3) 2.20(3) 2.921(3) 146(3) 1_655
N10 H10A N1 0.93(4) 2.23(4) 3.131(3) 162(3) 2_655

_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.
;



_refine_diff_density_max         0.398
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-4


