#------------------------------------------------------------------------------
#$Date: 2019-10-29 06:16:43 +0200 (Tue, 29 Oct 2019) $
#$Revision: 220352 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/89/7058944.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7058944
loop_
_publ_author_name
'Stierstorfer, Joerg'
'Wurzenberger, Maximilian Hans Horst'
'Lommel, Marcus'
'Gruhne, Michael S.'
'Szimhardt, Norbert'
'Bissinger, Benjamin'
_publ_section_title
;
 Synthesis and Comparison of Copper(II) Complexes with various
 N-Aminotetrazole Ligands Involving Trinitrophenol Anions
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/C9NJ03937F
_journal_year                    2019
_chemical_formula_moiety         'C14 H10 Cu N16 O14'
_chemical_formula_sum            'C14 H10 Cu N16 O14'
_chemical_formula_weight         689.92
_chemical_name_common
'bis(2-aminotetrazolyl) copper(II) bis(picrate)'
_chemical_name_systematic
;
bis(2-aminotetrazolyl) copper(II) bis(picrate)
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date
;
'Tue Apr 25 21:57:08 2017'
;
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-08-26 deposited with the CCDC.    2019-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.619(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.0030(8)
_cell_length_b                   13.5703(11)
_cell_length_c                   6.8287(5)
_cell_measurement_reflns_used    1403
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.9710
_cell_measurement_theta_min      4.4350
_cell_volume                     1202.55(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'enCIFer 1.5.1 (CCDC 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_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_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_sigmaI/netI    0.1883
_diffrn_reflns_av_unetI/netI     0.0853
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9343
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         4.238
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.017
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_description       needle
_exptl_crystal_F_000             694
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0118P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1648
_reflns_number_total             2359
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj03937f2.cif
_cod_data_source_block           mx190
_cod_database_code               7058944
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.605
_shelx_estimated_absorpt_t_max   0.951
_shelxl_version_number           2013-4
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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.0000 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_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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_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
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
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)
