#------------------------------------------------------------------------------
#$Date: 2022-09-15 01:51:06 +0300 (Thu, 15 Sep 2022) $
#$Revision: 277854 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/12/7711244.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_7711244
loop_
_publ_author_name
'Pramanik, Abhishek'
'Majumder, Samit'
'Sparkes, Hazel A.'
'Mohanta, Sasankasekhar'
_publ_section_title
;
 A metal complex based fluorescent chemodosimeter for selective detection
 of 2,4-dinitrophenol and picric acid in aqueous media
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01808J
_journal_year                    2022
_chemical_formula_moiety         'C16 H25 N13 O Zn2'
_chemical_formula_sum            'C16 H25 N13 O Zn2'
_chemical_formula_weight         546.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-15 deposited with the CCDC.	2022-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.723(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3387(7)
_cell_length_b                   10.7536(6)
_cell_length_c                   14.2438(8)
_cell_measurement_reflns_used    9423
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.80
_cell_measurement_theta_min      2.37
_cell_volume                     2196.1(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29945
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.420
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.223
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1277 before and 0.0742 after correction. The Ratio of minimum to maximum transmission is 0.6723. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.224
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4022
_refine_ls_number_restraints     191
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0158P)²+17.2997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1262
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3396
_reflns_number_total             4022
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt01808j3.cif
_cod_data_source_block           1
_cod_database_code               7711244
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_max   0.636
_shelx_estimated_absorpt_t_min   0.423
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C11A \\sim C7-C11
 with sigma of 0.01
 C12-C11 \\sim C12A-C11A
 with sigma of 0.01
 Zn1-N8A \\sim Zn1-N8
 with sigma of 0.01
 Zn2-N8A \\sim Zn2-N8
 with sigma of 0.01
 N12A-N13A \\sim N13-N12 \\sim N10-N9 \\sim N9A-N10A \\sim N7-N6
 with sigma of 0.01
 N12-N11 \\sim N12A-N11 \\sim N9-N8 \\sim N8A-N9A \\sim N5-N6
 with sigma of 0.01
3. Restrained planarity
 C5, C9, C10, C11A
 with sigma of 0.01
 C5, C9, C10, C6, C7, C8, C11
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C5 \\sim C9 \\sim C10 \\sim C6 \\sim C7 \\sim C8 \\sim C11 \\sim C12: within 2A
with sigma of 0.003 and sigma for terminal atoms of 0.006
N8 \\sim N9 \\sim N10 \\sim N8A \\sim N9A \\sim N10A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
N11 \\sim N12 \\sim N13 \\sim N12A \\sim N13A: within 2A with sigma of 0.003
and sigma for terminal atoms of 0.006
Uanis(C11A) = Uanis(C11)
5. Others
 Sof(N8A)=Sof(N9A)=Sof(N10A)=1-FVAR(1)
 Sof(N8)=Sof(N9)=Sof(N10)=FVAR(1)
 Sof(N12A)=Sof(N13A)=1-FVAR(2)
 Sof(N12)=Sof(N13)=FVAR(2)
 Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(3)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 N1(H1), N4(H4)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C14(H14A,H14B), C15(H15A,H15B), C11(H11A,H11B),
 C11A(H11C,H11D)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4A), C13(H13), C6(H6), C8(H8)
6.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C12(H12A,H12B,H12C), C12A(H12D,H12E,H12F)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.22433(4) 0.34383(5) 0.55428(5) 0.01819(18) Uani 1 1 d D . . . .
Zn2 Zn 0.19307(4) 0.63691(5) 0.52712(5) 0.01571(17) Uani 1 1 d D . . . .
O1 O 0.2712(2) 0.4907(3) 0.4745(3) 0.0211(9) Uani 1 1 d . . . . .
N1 N 0.2252(3) 0.2207(4) 0.6720(4) 0.0253(11) Uani 1 1 d . . . . .
H1 H 0.252304 0.265403 0.727539 0.030 Uiso 1 1 calc R . . . .
N2 N 0.3602(3) 0.2818(4) 0.5467(4) 0.0208(11) Uani 1 1 d . . . . .
N3 N 0.2047(3) 0.7075(4) 0.3921(3) 0.0181(10) Uani 1 1 d . . . . .
N4 N 0.0807(3) 0.7673(4) 0.5323(3) 0.0174(10) Uani 1 1 d . . . . .
H4 H 0.021752 0.726106 0.510535 0.021 Uiso 1 1 calc R . . . .
N5 N 0.1364(3) 0.2463(5) 0.4728(4) 0.0277(12) Uani 1 1 d D . . . .
N6 N 0.1632(3) 0.1838(4) 0.4104(3) 0.0228(11) Uani 1 1 d D . . . .
N7 N 0.1855(4) 0.1199(5) 0.3486(4) 0.0381(14) Uani 1 1 d D . . . .
N11 N 0.2889(3) 0.7338(4) 0.6026(4) 0.0278(11) Uani 1 1 d D U . . .
C1 C 0.1338(4) 0.1674(6) 0.6984(5) 0.0340(16) Uani 1 1 d . . . . .
H1A H 0.093724 0.233400 0.722750 0.051 Uiso 1 1 calc GR . . . .
H1B H 0.143300 0.103739 0.746841 0.051 Uiso 1 1 calc GR . . . .
H1C H 0.104044 0.129654 0.643003 0.051 Uiso 1 1 calc GR . . . .
C2 C 0.2903(4) 0.1219(6) 0.6437(5) 0.0324(15) Uani 1 1 d . . . . .
H2A H 0.262665 0.073388 0.591289 0.039 Uiso 1 1 calc R . . . .
H2B H 0.301747 0.064741 0.697104 0.039 Uiso 1 1 calc R . . . .
C3 C 0.3823(4) 0.1801(5) 0.6130(5) 0.0276(14) Uani 1 1 d . . . . .
H3A H 0.416854 0.213009 0.668258 0.033 Uiso 1 1 calc R . . . .
H3B H 0.421601 0.116760 0.582206 0.033 Uiso 1 1 calc R . . . .
C4 C 0.4257(4) 0.3185(5) 0.4931(4) 0.0238(13) Uani 1 1 d . . . . .
H4A H 0.483442 0.275697 0.498237 0.029 Uiso 1 1 calc R . . . .
C5 C 0.4205(4) 0.4188(5) 0.4253(4) 0.0235(10) Uani 1 1 d . U . . .
C9 C 0.3469(3) 0.5980(5) 0.3516(4) 0.0220(10) Uani 1 1 d . U . . .
C10 C 0.3428(3) 0.5032(5) 0.4188(4) 0.0207(9) Uani 1 1 d . U . . .
C13 C 0.2731(4) 0.6909(5) 0.3374(4) 0.0216(12) Uani 1 1 d . . . . .
H13 H 0.276693 0.742496 0.283464 0.026 Uiso 1 1 calc R . . . .
C14 C 0.1349(4) 0.8030(5) 0.3714(4) 0.0231(13) Uani 1 1 d . . . . .
H14A H 0.079421 0.765190 0.340758 0.028 Uiso 1 1 calc R . . . .
H14B H 0.160922 0.866150 0.328468 0.028 Uiso 1 1 calc R . . . .
C15 C 0.1078(4) 0.8633(5) 0.4635(4) 0.0203(12) Uani 1 1 d . . . . .
H15A H 0.161084 0.911916 0.488823 0.024 Uiso 1 1 calc R . . . .
H15B H 0.055005 0.921080 0.452569 0.024 Uiso 1 1 calc R . . . .
C16 C 0.0673(4) 0.8196(5) 0.6259(4) 0.0247(13) Uani 1 1 d . . . . .
H16A H 0.042549 0.755335 0.667553 0.037 Uiso 1 1 calc GR . . . .
H16B H 0.023171 0.889071 0.622048 0.037 Uiso 1 1 calc GR . . . .
H16C H 0.127208 0.849463 0.650982 0.037 Uiso 1 1 calc GR . . . .
N8 N 0.1464(10) 0.4914(6) 0.6067(11) 0.025(2) Uani 0.74(3) 1 d D U P A 1
N9 N 0.0741(7) 0.4805(12) 0.6471(10) 0.026(2) Uani 0.74(3) 1 d D U P A 1
N10 N 0.0053(9) 0.4744(10) 0.6879(13) 0.041(4) Uani 0.74(3) 1 d D U P A 1
N12 N 0.3315(13) 0.8071(17) 0.5563(12) 0.0272(15) Uani 0.56(4) 1 d D U P B 1
N13 N 0.3745(10) 0.8791(11) 0.5131(15) 0.030(2) Uani 0.56(4) 1 d D U P B 1
C6 C 0.4956(4) 0.4345(6) 0.3660(4) 0.0290(10) Uani 1 1 d . U . . .
H6 H 0.546525 0.378371 0.371693 0.035 Uiso 1 1 calc R . . . .
C7 C 0.5003(4) 0.5266(6) 0.2997(4) 0.0334(10) Uani 1 1 d D U . . .
C8 C 0.4249(4) 0.6092(6) 0.2920(4) 0.0285(10) Uani 1 1 d . U . . .
H8 H 0.426035 0.673410 0.246240 0.034 Uiso 1 1 calc R . . . .
C11 C 0.5901(6) 0.5255(10) 0.2408(6) 0.0367(16) Uani 0.607(14) 1 d D U P C 1
H11A H 0.642835 0.556953 0.279540 0.044 Uiso 0.607(14) 1 calc R . P C 1
H11B H 0.604596 0.438952 0.222304 0.044 Uiso 0.607(14) 1 calc R . P C 1
C12 C 0.5806(7) 0.6002(11) 0.1586(8) 0.037(3) Uani 0.607(14) 1 d D U P C 1
H12A H 0.522375 0.578812 0.125629 0.056 Uiso 0.607(14) 1 calc GR . P C 1
H12B H 0.633466 0.585061 0.117207 0.056 Uiso 0.607(14) 1 calc GR . P C 1
H12C H 0.579362 0.688230 0.176442 0.056 Uiso 0.607(14) 1 calc GR . P C 1
N8A N 0.140(3) 0.4890(13) 0.599(3) 0.026(3) Uani 0.26(3) 1 d D U P A 2
N9A N 0.060(2) 0.480(4) 0.620(3) 0.027(3) Uani 0.26(3) 1 d D U P A 2
N10A N -0.017(2) 0.464(3) 0.640(4) 0.038(5) Uani 0.26(3) 1 d D U P A 2
N12A N 0.3384(17) 0.811(2) 0.5716(17) 0.0273(15) Uani 0.44(4) 1 d D U P B 2
N13A N 0.3898(11) 0.8872(13) 0.547(2) 0.029(2) Uani 0.44(4) 1 d D U P B 2
C11A C 0.5757(9) 0.5606(15) 0.2286(8) 0.0367(16) Uani 0.393(14) 1 d D . P C 2
H11C H 0.557969 0.641656 0.200720 0.044 Uiso 0.393(14) 1 calc R . P C 2
H11D H 0.634319 0.574340 0.264663 0.044 Uiso 0.393(14) 1 calc R . P C 2
C12A C 0.5966(12) 0.4810(15) 0.1547(13) 0.040(5) Uani 0.393(14) 1 d D . P C 2
H12D H 0.651125 0.512596 0.121408 0.060 Uiso 0.393(14) 1 calc GR . P C 2
H12E H 0.543184 0.476528 0.111283 0.060 Uiso 0.393(14) 1 calc GR . P C 2
H12F H 0.610301 0.397831 0.179434 0.060 Uiso 0.393(14) 1 calc GR . P C 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 N1 155.21(18) . . ?
O1 Zn1 N2 84.50(16) . . ?
O1 Zn1 N8 78.13(17) . . ?
O1 Zn1 N8A 78.0(3) . . ?
N2 Zn1 N1 81.06(18) . . ?
N2 Zn1 N8 140.9(5) . . ?
N2 Zn1 N8A 144.3(15) . . ?
N5 Zn1 O1 106.8(2) . . ?
N5 Zn1 N1 97.4(2) . . ?
N5 Zn1 N2 112.88(19) . . ?
N5 Zn1 N8 105.7(6) . . ?
N5 Zn1 N8A 101.9(16) . . ?
N8 Zn1 N1 100.9(3) . . ?
N8A Zn1 N1 102.7(9) . . ?
O1 Zn2 N3 83.84(17) . . ?
O1 Zn2 N4 156.87(18) . . ?
N3 Zn2 N4 82.02(17) . . ?
N11 Zn2 O1 102.45(17) . . ?
N11 Zn2 N3 104.01(19) . . ?
N11 Zn2 N4 98.69(18) . . ?
N11 Zn2 N8 108.9(6) . . ?
N11 Zn2 N8A 112.9(17) . . ?
N8 Zn2 O1 78.63(18) . . ?
N8 Zn2 N3 145.3(5) . . ?
N8 Zn2 N4 103.3(3) . . ?
N8A Zn2 O1 78.5(3) . . ?
N8A Zn2 N3 141.7(16) . . ?
N8A Zn2 N4 101.9(6) . . ?
Zn1 O1 Zn2 101.54(15) . . ?
C10 O1 Zn1 132.4(3) . . ?
C10 O1 Zn2 124.8(3) . . ?
Zn1 N1 H1 108.7 . . ?
C1 N1 Zn1 116.2(4) . . ?
C1 N1 H1 108.7 . . ?
C2 N1 Zn1 103.3(4) . . ?
C2 N1 H1 108.7 . . ?
C2 N1 C1 110.8(5) . . ?
C3 N2 Zn1 113.6(3) . . ?
C4 N2 Zn1 129.2(4) . . ?
C4 N2 C3 117.2(5) . . ?
C13 N3 Zn2 125.9(4) . . ?
C13 N3 C14 120.4(5) . . ?
C14 N3 Zn2 112.4(3) . . ?
Zn2 N4 H4 109.4 . . ?
C15 N4 Zn2 103.3(3) . . ?
C15 N4 H4 109.4 . . ?
C16 N4 Zn2 113.0(3) . . ?
C16 N4 H4 109.4 . . ?
C16 N4 C15 112.0(4) . . ?
N6 N5 Zn1 121.8(4) . . ?
N7 N6 N5 176.9(6) . . ?
N12 N11 Zn2 113.2(10) . . ?
N12A N11 Zn2 124.8(13) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
N1 C2 C3 109.6(5) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
N2 C3 C2 107.9(5) . . ?
N2 C3 H3A 110.1 . . ?
N2 C3 H3B 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N2 C4 H4A 116.7 . . ?
N2 C4 C5 126.5(5) . . ?
C5 C4 H4A 116.7 . . ?
C10 C5 C4 123.1(5) . . ?
C6 C5 C4 117.5(5) . . ?
C6 C5 C10 119.3(6) . . ?
C10 C9 C13 123.7(5) . . ?
C10 C9 C8 120.7(5) . . ?
C8 C9 C13 115.6(5) . . ?
O1 C10 C5 120.4(5) . . ?
O1 C10 C9 121.8(5) . . ?
C9 C10 C5 117.8(5) . . ?
N3 C13 C9 124.8(5) . . ?
N3 C13 H13 117.6 . . ?
C9 C13 H13 117.6 . . ?
N3 C14 H14A 110.1 . . ?
N3 C14 H14B 110.1 . . ?
N3 C14 C15 107.9(5) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
N4 C15 C14 110.3(4) . . ?
N4 C15 H15A 109.6 . . ?
N4 C15 H15B 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Zn2 N8 Zn1 101.7(2) . . ?
N9 N8 Zn1 124.7(8) . . ?
N9 N8 Zn2 129.2(8) . . ?
N10 N9 N8 177.2(14) . . ?
N13 N12 N11 178.3(17) . . ?
C5 C6 H6 118.2 . . ?
C7 C6 C5 123.5(6) . . ?
C7 C6 H6 118.2 . . ?
C6 C7 C8 117.8(6) . . ?
C6 C7 C11 114.6(7) . . ?
C6 C7 C11A 131.9(9) . . ?
C8 C7 C11 127.5(7) . . ?
C8 C7 C11A 110.3(9) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 C9 120.9(6) . . ?
C7 C8 H8 119.6 . . ?
C7 C11 H11A 109.3 . . ?
C7 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C7 111.7(8) . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Zn2 N8A Zn1 101.8(4) . . ?
N9A N8A Zn1 125(3) . . ?
N9A N8A Zn2 124(3) . . ?
N10A N9A N8A 176(4) . . ?
N13A N12A N11 175(2) . . ?
C7 C11A H11C 107.1 . . ?
C7 C11A H11D 107.1 . . ?
H11C C11A H11D 106.8 . . ?
C12A C11A C7 120.8(11) . . ?
C12A C11A H11C 107.1 . . ?
C12A C11A H11D 107.1 . . ?
C11A C12A H12D 109.5 . . ?
C11A C12A H12E 109.5 . . ?
C11A C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
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
Zn1 O1 2.063(4) . ?
Zn1 N1 2.136(5) . ?
Zn1 N2 2.064(4) . ?
Zn1 N5 1.999(5) . ?
Zn1 N8 2.085(5) . ?
Zn1 N8A 2.084(9) . ?
Zn2 O1 2.076(4) . ?
Zn2 N3 2.076(5) . ?
Zn2 N4 2.138(4) . ?
Zn2 N11 2.023(5) . ?
Zn2 N8 2.050(5) . ?
Zn2 N8A 2.048(9) . ?
O1 C10 1.313(6) . ?
N1 H1 1.0000 . ?
N1 C1 1.483(7) . ?
N1 C2 1.473(8) . ?
N2 C3 1.477(7) . ?
N2 C4 1.279(7) . ?
N3 C13 1.273(7) . ?
N3 C14 1.462(7) . ?
N4 H4 1.0000 . ?
N4 C15 1.478(7) . ?
N4 C16 1.463(8) . ?
N5 N6 1.182(6) . ?
N6 N7 1.164(6) . ?
N11 N12 1.199(7) . ?
N11 N12A 1.182(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.529(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9500 . ?
C4 C5 1.448(8) . ?
C5 C10 1.438(8) . ?
C5 C6 1.388(8) . ?
C9 C10 1.400(8) . ?
C9 C13 1.467(8) . ?
C9 C8 1.418(8) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.518(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N8 N9 1.197(6) . ?
N9 N10 1.153(7) . ?
N12 N13 1.170(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.371(9) . ?
C7 C8 1.402(9) . ?
C7 C11 1.547(9) . ?
C7 C11A 1.535(11) . ?
C8 H8 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.425(13) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N8A N9A 1.192(9) . ?
N9A N10A 1.157(9) . ?
N12A N13A 1.157(8) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C11A C12A 1.393(13) . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
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
Zn1 O1 C10 C5 -18.7(6) . . . . ?
Zn1 O1 C10 C9 161.5(3) . . . . ?
Zn1 N1 C2 C3 52.5(6) . . . . ?
Zn1 N2 C3 C2 18.9(6) . . . . ?
Zn1 N2 C4 C5 2.6(9) . . . . ?
Zn2 O1 C10 C5 145.9(3) . . . . ?
Zn2 O1 C10 C9 -33.9(5) . . . . ?
Zn2 N3 C13 C9 13.7(8) . . . . ?
Zn2 N3 C14 C15 26.7(5) . . . . ?
Zn2 N4 C15 C14 49.7(5) . . . . ?
N1 C2 C3 N2 -48.6(7) . . . . ?
N2 C4 C5 C10 9.1(8) . . . . ?
N2 C4 C5 C6 -172.5(5) . . . . ?
N3 C14 C15 N4 -52.3(6) . . . . ?
C1 N1 C2 C3 177.6(5) . . . . ?
C3 N2 C4 C5 -177.9(5) . . . . ?
C4 N2 C3 C2 -160.6(6) . . . . ?
C4 C5 C10 O1 -1.1(5) . . . . ?
C4 C5 C10 C9 178.7(5) . . . . ?
C4 C5 C6 C7 -179.1(5) . . . . ?
C5 C6 C7 C8 0.2(7) . . . . ?
C5 C6 C7 C11 -179.4(4) . . . . ?
C5 C6 C7 C11A 179.5(4) . . . . ?
C10 C5 C6 C7 -0.6(5) . . . . ?
C10 C9 C13 N3 10.7(8) . . . . ?
C10 C9 C8 C7 -0.9(5) . . . . ?
C13 N3 C14 C15 -141.3(5) . . . . ?
C13 C9 C10 O1 0.1(5) . . . . ?
C13 C9 C10 C5 -179.7(5) . . . . ?
C13 C9 C8 C7 179.3(5) . . . . ?
C14 N3 C13 C9 179.9(5) . . . . ?
C16 N4 C15 C14 171.6(4) . . . . ?
C6 C5 C10 O1 -179.5(4) . . . . ?
C6 C5 C10 C9 0.2(2) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C6 C7 C11 C12 164.6(7) . . . . ?
C6 C7 C11A C12A 66.8(18) . . . . ?
C8 C9 C10 O1 -179.8(4) . . . . ?
C8 C9 C10 C5 0.5(2) . . . . ?
C8 C9 C13 N3 -169.4(5) . . . . ?
C8 C7 C11 C12 -14.9(10) . . . . ?
C8 C7 C11A C12A -113.8(17) . . . . ?
C11 C7 C8 C9 -180.0(4) . . . . ?
C11A C7 C8 C9 -178.9(4) . . . . ?
