#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:50:25 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299034 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/36/7063639.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_7063639
loop_
_publ_author_name
'Hasić, Rušid'
'Serezlić, Majda Kolenović'
'Caković, Angelina'
'Bogojeski, Jovana'
'Nikodijević, Danijela'
'Milutinović, Milena'
'Stanojević, Aleksandra'
'Čavić, Milena'
'Egorov, Andrei V.'
'Komolkin, Andrei V.'
'Kornyakov, Ilya V.'
'Scheurer, Andreas'
'Puchta, Ralph'
'Soldatović, Tanja V.'
_publ_section_title
;
 New bis-pyrazolate zinc(ii) complexes as potential anticancer drugs: from
 structure to anticancer activity
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3617
_journal_page_last               3632
_journal_paper_doi               10.1039/D5NJ00043B
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C19 H25 Cl2 N5 Zn, 2.459(H2 O)'
_chemical_formula_sum            'C19 H29.92 Cl2 N5 O2.46 Zn'
_chemical_formula_weight         504.03
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-02-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-03-12 deposited with the CCDC.	2025-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                67.436(3)
_cell_angle_beta                 84.168(3)
_cell_angle_gamma                75.427(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0761(4)
_cell_length_b                   11.1556(5)
_cell_length_c                   11.5131(4)
_cell_measurement_reflns_used    10571
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.4310
_cell_measurement_theta_min      4.1450
_cell_volume                     1156.60(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -38.00   0.50    0.70    --  -47.51 -28.00  44.00  156
  2  ω    -12.00  14.00   0.50    0.70    --  -47.51  28.00-153.00   52
  3  ω     37.00 118.00   0.50    0.70    --   47.51  28.00-153.00  162
  4  ω   -176.00-109.00   0.50    2.00    -- -106.00 -28.00  44.00  134
  5  ω    141.00 178.00   0.50    2.00    --  113.25  28.00-153.00   74
  6  ω    111.00 138.00   0.50    2.00    --  113.25  28.00-153.00   54
  7  ω    -57.00  24.00   0.50    0.70    --  -47.51  57.00 -30.00  162
  8  ω   -110.00 -85.00   0.50    0.70    --  -47.51-125.00 -30.00   50
  9  ω     76.00 117.00   0.50    0.70    --   47.51 125.00-120.00   82
 10  ω    -21.00   4.00   0.50    0.70    --   47.51 -28.00  44.00   50
 11  ω    -27.00  19.00   0.50    0.70    --   47.51 -19.00 -90.00   92
 12  ω    -22.00  68.00   0.50    0.70    --   47.51 -77.00-180.00  180
 13  ω    -70.00 -36.00   0.50    2.00    -- -106.00  61.00-180.00   68
 14  ω   -118.00 -93.00   0.50    2.00    -- -106.00 -30.00   0.00   50
 15  ω    -83.00 -42.00   0.50    2.00    -- -106.00 144.00-175.07   82
 16  ω   -120.00 -93.00   0.50    2.00    -- -106.00 136.00 -16.32   54
 17  ω   -131.00 -99.00   0.50    2.00    -- -106.00 -77.00   0.00   64
 18  ω    -76.00 -33.00   0.50    2.00    -- -106.00 125.00 -90.00   86
 19  ω   -107.00 -78.00   0.50    2.00    -- -106.00 125.00 -30.00   58
 20  ω   -108.00 -83.00   0.50    2.00    -- -106.00 109.00  55.12   50
 21  ω    -71.00 -33.00   0.50    2.00    -- -106.00  61.00   0.00   76
 22  ω   -111.00 -82.00   0.50    2.00    -- -106.00 125.00-180.00   58
 23  ω   -108.00 -80.00   0.50    2.00    -- -106.00 110.00  96.43   56
 24  ω   -142.00-107.00   0.50    2.00    -- -106.00 -30.00 -90.00   70
 25  ω   -126.00-101.00   0.50    2.00    -- -106.00 144.00-108.68   50
 26  ω    -64.00 -36.00   0.50    2.00    -- -106.00 109.00  55.12   56
 27  ω   -176.00-136.00   0.50    2.00    -- -106.00 -30.00   0.00   80
 28  ω   -177.00-139.00   0.50    2.00    -- -106.00 -77.00   0.00   76
 29  ω   -111.00 -85.00   0.50    2.00    -- -106.00 125.00 -90.00   52
 30  ω    -68.00 -42.00   0.50    2.00    -- -106.00 144.00-108.68   52
 31  ω   -126.00 -89.00   0.50    2.00    -- -106.00 144.00 109.55   74
 32  ω    -82.00 -56.00   0.50    2.00    -- -106.00 144.00 109.55   52
 33  ω    -71.00 -41.00   0.50    2.00    -- -106.00 125.00-180.00   60
 34  ω    -72.00 -36.00   0.50    2.00    -- -106.00 125.00 -30.00   72
 35  ω   -126.00 -92.00   0.50    2.00    -- -106.00 144.00-175.07   68
 36  ω     43.00  75.00   0.50    2.00    --  113.25 -94.00-180.00   64
 37  ω    101.00 149.00   0.50    2.00    --  113.25  15.00 120.00   96
 38  ω     43.00  69.00   0.50    2.00    --  113.25 -61.00  30.00   52
 39  ω     43.00 105.00   0.50    2.00    --  113.25 -77.00 -30.00  124
 40  ω     42.00 104.00   0.50    2.00    --  113.25 -94.00  60.00  124
 41  ω     53.00 103.00   0.50    2.00    --  113.25 -77.00-180.00  100
 42  ω     42.00  86.00   0.50    2.00    --  113.25 -94.00 -60.00   88
 43  ω     44.00 100.00   0.50    2.00    --  113.25 -94.00 120.00  112
 44  ω     45.00  70.00   0.50    2.00    --  113.25 -61.00-150.00   50
 45  ω     45.00  70.00   0.50    2.00    --  113.25 -61.00 120.00   50
 46  ω    126.00 176.00   0.50    2.00    --  113.25 125.00  30.00  100
 47  ω     44.00  69.00   0.50    2.00    --  113.25 -61.00-180.00   50
 48  ω     76.00 115.00   0.50    2.00    --  113.25 125.00  30.00   78
 49  ω    118.00 175.00   0.50    2.00    --  113.25  45.00 150.00  114
 50  ω    109.00 175.00   0.50    2.00    --  113.25  30.00 -90.00  132
 51  ω    153.00 178.00   0.50    2.00    --  113.25  15.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1475324000
_diffrn_orient_matrix_UB_12      0.0849040000
_diffrn_orient_matrix_UB_13      -0.0307476000
_diffrn_orient_matrix_UB_21      0.0335954000
_diffrn_orient_matrix_UB_22      0.1036071000
_diffrn_orient_matrix_UB_23      0.0433434000
_diffrn_orient_matrix_UB_31      0.0454140000
_diffrn_orient_matrix_UB_32      0.0754107000
_diffrn_orient_matrix_UB_33      -0.1348076000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15818
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.187
_diffrn_reflns_theta_min         4.158
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.823
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       prism
_exptl_crystal_F_000             525
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4845
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0317
_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)+(0.0240P)²+0.7582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4272
_reflns_number_total             4845
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj00043b2.cif
_cod_data_source_block           2ver0-26329_iii
_cod_depositor_comments
'Adding full bibliography for 7063638--7063639.cif.'
_cod_database_code               7063639
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'Zn Cl2 C19 H25 N5'
_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   0.894
_shelx_estimated_absorpt_t_min   0.832
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H4B-O4
 0.96 with sigma of 0.02
 H3B-O3
 0.96 with sigma of 0.02
 H1A-O1
 0.96 with sigma of 0.02
 H1B-O1
 0.96 with sigma of 0.02
 H2A-O2
 0.96 with sigma of 0.02
 O3-H3A
 0.96 with sigma of 0.02
 H2B-O2
 0.96 with sigma of 0.02
 H4A-O4
 0.96 with sigma of 0.02
 H1B-H1A
 1.52 with sigma of 0.04
 H4A-H4B
 1.52 with sigma of 0.04
 H3B-H3A
 1.52 with sigma of 0.04
 H2B-H2A
 1.52 with sigma of 0.04
3. Others
 Sof(O2)=Sof(H2A)=Sof(H2B)=Sof(O4)=Sof(H4A)=Sof(H4B)=1-FVAR(1)
 Sof(O3)=Sof(H3A)=Sof(H3B)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N5(H5), C2(H2), C3(H3), C4(H4), C7(H7), C14(H14)
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.097
_oxdiff_exptl_absorpt_empirical_full_min 0.480
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.27412(3) 0.50800(2) 0.25776(2) 0.01579(8) Uani 1 1 d . . . . .
Cl1 Cl 0.20094(5) 0.37173(5) 0.18674(5) 0.02679(12) Uani 1 1 d . . . . .
Cl2 Cl 0.41911(5) 0.63258(5) 0.13334(4) 0.02107(11) Uani 1 1 d . . . . .
N1 N 0.54767(17) 0.26019(16) 0.38920(14) 0.0198(3) Uani 1 1 d . . . . .
H1 H 0.576010 0.238975 0.323228 0.024 Uiso 1 1 calc R U . . .
N2 N 0.43747(17) 0.35757(16) 0.38822(14) 0.0193(3) Uani 1 1 d . . . . .
N3 N 0.22578(16) 0.52377(16) 0.43433(14) 0.0169(3) Uani 1 1 d . . . . .
N4 N 0.08024(16) 0.65701(16) 0.23027(14) 0.0169(3) Uani 1 1 d . . . . .
N5 N -0.01157(16) 0.73543(16) 0.13852(14) 0.0181(3) Uani 1 1 d . . . . .
H5 H -0.002538 0.737754 0.060902 0.022 Uiso 1 1 calc R U . . .
C1 C 0.3120(2) 0.45154(19) 0.53204(16) 0.0180(4) Uani 1 1 d . . . . .
C2 C 0.2839(2) 0.4630(2) 0.64865(17) 0.0216(4) Uani 1 1 d . . . . .
H2 H 0.347483 0.415806 0.715718 0.026 Uiso 1 1 calc R U . . .
C3 C 0.1610(2) 0.5451(2) 0.66445(17) 0.0219(4) Uani 1 1 d . . . . .
H3 H 0.138096 0.551849 0.744164 0.026 Uiso 1 1 calc R U . . .
C4 C 0.0704(2) 0.6180(2) 0.56410(18) 0.0208(4) Uani 1 1 d . . . . .
H4 H -0.014779 0.673415 0.574444 0.025 Uiso 1 1 calc R U . . .
C5 C 0.10887(19) 0.60694(19) 0.44859(17) 0.0172(3) Uani 1 1 d . . . . .
C6 C 0.02807(19) 0.68193(19) 0.33271(17) 0.0172(4) Uani 1 1 d . . . . .
C7 C -0.0961(2) 0.7772(2) 0.30569(17) 0.0195(4) Uani 1 1 d . . . . .
H7 H -0.152725 0.812020 0.361903 0.023 Uiso 1 1 calc R U . . .
C8 C -0.11906(19) 0.8101(2) 0.17923(17) 0.0188(4) Uani 1 1 d . . . . .
C9 C -0.2344(2) 0.9080(2) 0.09328(19) 0.0249(4) Uani 1 1 d . . . . .
C10 C -0.3435(3) 0.9652(5) 0.1711(3) 0.0844(16) Uani 1 1 d . . . . .
H10A H -0.381846 0.893438 0.233057 0.127 Uiso 1 1 calc R U . . .
H10B H -0.416674 1.032193 0.115789 0.127 Uiso 1 1 calc R U . . .
H10C H -0.302447 1.007016 0.214792 0.127 Uiso 1 1 calc R U . . .
C11 C -0.1801(3) 1.0227(2) -0.0060(3) 0.0396(6) Uani 1 1 d . . . . .
H11A H -0.140293 1.067101 0.035792 0.059 Uiso 1 1 calc R U . . .
H11B H -0.255623 1.086979 -0.060079 0.059 Uiso 1 1 calc R U . . .
H11C H -0.109613 0.987261 -0.057200 0.059 Uiso 1 1 calc R U . . .
C12 C -0.2930(3) 0.8391(3) 0.0263(3) 0.0497(8) Uani 1 1 d . . . . .
H12A H -0.221472 0.806359 -0.025768 0.075 Uiso 1 1 calc R U . . .
H12B H -0.369383 0.902630 -0.027150 0.075 Uiso 1 1 calc R U . . .
H12C H -0.326004 0.763810 0.088705 0.075 Uiso 1 1 calc R U . . .
C13 C 0.4298(2) 0.35878(19) 0.50438(17) 0.0187(4) Uani 1 1 d . . . . .
C14 C 0.5366(2) 0.2617(2) 0.57936(17) 0.0217(4) Uani 1 1 d . . . . .
H14 H 0.554518 0.243452 0.664659 0.026 Uiso 1 1 calc R U . . .
C15 C 0.6110(2) 0.19774(19) 0.50264(17) 0.0190(4) Uani 1 1 d . . . . .
C16 C 0.7276(2) 0.0758(2) 0.53084(18) 0.0217(4) Uani 1 1 d . . . . .
C17 C 0.7995(2) 0.0531(2) 0.6507(2) 0.0283(4) Uani 1 1 d . . . . .
H17A H 0.838318 0.129582 0.637622 0.042 Uiso 1 1 calc R U . . .
H17B H 0.873172 -0.028086 0.671251 0.042 Uiso 1 1 calc R U . . .
H17C H 0.733099 0.043293 0.720213 0.042 Uiso 1 1 calc R U . . .
C18 C 0.6708(2) -0.0469(2) 0.5526(2) 0.0275(4) Uani 1 1 d . . . . .
H18A H 0.602863 -0.056598 0.620882 0.041 Uiso 1 1 calc R U . . .
H18B H 0.745932 -0.126933 0.575375 0.041 Uiso 1 1 calc R U . . .
H18C H 0.627270 -0.035212 0.475426 0.041 Uiso 1 1 calc R U . . .
C19 C 0.8290(2) 0.0915(2) 0.4203(2) 0.0266(4) Uani 1 1 d . . . . .
H19A H 0.779859 0.111590 0.343357 0.040 Uiso 1 1 calc R U . . .
H19B H 0.899538 0.008457 0.437384 0.040 Uiso 1 1 calc R U . . .
H19C H 0.872252 0.164640 0.409383 0.040 Uiso 1 1 calc R U . . .
O1 O 0.95240(17) 0.27380(17) 0.10078(14) 0.0295(3) Uani 1 1 d D . . . .
H1A H 1.014(3) 0.311(3) 0.124(3) 0.044 Uiso 1 1 d D U . . .
H1B H 0.867(2) 0.330(3) 0.100(3) 0.044 Uiso 1 1 d D U . . .
O2 O 0.7203(4) 0.4688(4) 0.0881(3) 0.0322(9) Uani 0.459(4) 1 d D . P A 1
H2A H 0.627(3) 0.501(7) 0.108(6) 0.048 Uiso 0.459(4) 1 d D U P A 1
H2B H 0.726(6) 0.524(6) 0.000(3) 0.048 Uiso 0.459(4) 1 d D U P A 1
O4 O 0.5147(4) 0.2437(4) 0.1616(3) 0.0279(9) Uani 0.459(4) 1 d D . P A 1
H4A H 0.552(5) 0.272(6) 0.079(3) 0.042 Uiso 0.459(4) 1 d D U P A 1
H4B H 0.420(3) 0.290(6) 0.150(5) 0.042 Uiso 0.459(4) 1 d D U P A 1
O3 O 0.6544(3) 0.3543(3) 0.1354(2) 0.0264(7) Uani 0.541(4) 1 d D . P A 2
H3A H 0.629(5) 0.346(5) 0.064(3) 0.040 Uiso 0.541(4) 1 d D U P A 2
H3B H 0.604(5) 0.438(3) 0.135(5) 0.040 Uiso 0.541(4) 1 d D U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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
Cl1 Zn1 Cl2 118.25(2) . . ?
N2 Zn1 Cl1 99.19(5) . . ?
N2 Zn1 Cl2 94.68(4) . . ?
N3 Zn1 Cl1 125.39(4) . . ?
N3 Zn1 Cl2 116.31(4) . . ?
N3 Zn1 N2 73.99(6) . . ?
N3 Zn1 N4 74.89(6) . . ?
N4 Zn1 Cl1 96.25(4) . . ?
N4 Zn1 Cl2 101.69(4) . . ?
N4 Zn1 N2 148.74(6) . . ?
N2 N1 H1 123.5 . . ?
N2 N1 C15 112.98(16) . . ?
C15 N1 H1 123.5 . . ?
N1 N2 Zn1 139.96(12) . . ?
C13 N2 Zn1 114.94(13) . . ?
C13 N2 N1 105.11(15) . . ?
C1 N3 Zn1 120.24(13) . . ?
C5 N3 Zn1 119.42(12) . . ?
C5 N3 C1 120.34(16) . . ?
N5 N4 Zn1 139.47(12) . . ?
C6 N4 Zn1 115.51(12) . . ?
C6 N4 N5 105.00(15) . . ?
N4 N5 H5 123.8 . . ?
N4 N5 C8 112.40(15) . . ?
C8 N5 H5 123.8 . . ?
N3 C1 C2 121.22(19) . . ?
N3 C1 C13 113.89(16) . . ?
C2 C1 C13 124.82(17) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.30(18) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.48(18) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.92(19) . . ?
C5 C4 H4 121.0 . . ?
N3 C5 C4 121.60(17) . . ?
N3 C5 C6 113.95(16) . . ?
C4 C5 C6 124.45(18) . . ?
N4 C6 C5 116.20(17) . . ?
N4 C6 C7 111.06(16) . . ?
C7 C6 C5 132.74(18) . . ?
C6 C7 H7 127.4 . . ?
C8 C7 C6 105.29(17) . . ?
C8 C7 H7 127.4 . . ?
N5 C8 C7 106.23(17) . . ?
N5 C8 C9 122.44(17) . . ?
C7 C8 C9 131.32(18) . . ?
C8 C9 C10 108.73(18) . . ?
C8 C9 C11 109.76(17) . . ?
C8 C9 C12 110.13(19) . . ?
C10 C9 C11 108.5(3) . . ?
C10 C9 C12 111.2(3) . . ?
C12 C9 C11 108.46(19) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C1 116.64(17) . . ?
N2 C13 C14 110.94(17) . . ?
C14 C13 C1 132.31(17) . . ?
C13 C14 H14 127.3 . . ?
C15 C14 C13 105.47(16) . . ?
C15 C14 H14 127.3 . . ?
N1 C15 C14 105.48(17) . . ?
N1 C15 C16 122.69(17) . . ?
C14 C15 C16 131.52(17) . . ?
C15 C16 C17 109.22(17) . . ?
C15 C16 C18 109.39(16) . . ?
C15 C16 C19 110.77(16) . . ?
C17 C16 C18 108.51(17) . . ?
C17 C16 C19 110.74(17) . . ?
C19 C16 C18 108.18(17) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H1A O1 H1B 105(2) . . ?
H2A O2 H2B 102(4) . . ?
H4A O4 H4B 103(4) . . ?
H3A O3 H3B 107(3) . . ?
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 Cl1 2.2724(5) . ?
Zn1 Cl2 2.2774(5) . ?
Zn1 N2 2.2269(16) . ?
Zn1 N3 2.1049(15) . ?
Zn1 N4 2.1835(16) . ?
N1 H1 0.8800 . ?
N1 N2 1.341(2) . ?
N1 C15 1.358(2) . ?
N2 C13 1.337(2) . ?
N3 C1 1.349(2) . ?
N3 C5 1.343(3) . ?
N4 N5 1.349(2) . ?
N4 C6 1.340(2) . ?
N5 H5 0.8800 . ?
N5 C8 1.352(3) . ?
C1 C2 1.391(3) . ?
C1 C13 1.462(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 C6 1.471(3) . ?
C6 C7 1.395(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(3) . ?
C8 C9 1.513(3) . ?
C9 C10 1.518(4) . ?
C9 C11 1.532(3) . ?
C9 C12 1.520(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.401(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 C16 1.507(3) . ?
C16 C17 1.528(3) . ?
C16 C18 1.539(3) . ?
C16 C19 1.532(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O1 H1A 0.938(17) . ?
O1 H1B 0.928(17) . ?
O2 H2A 0.96(2) . ?
O2 H2B 0.97(2) . ?
O4 H4A 0.947(19) . ?
O4 H4B 0.96(2) . ?
O3 H3A 0.933(19) . ?
O3 H3B 0.940(19) . ?
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 N2 C13 C1 3.7(2) . . . . ?
Zn1 N2 C13 C14 -179.69(13) . . . . ?
Zn1 N3 C1 C2 178.26(14) . . . . ?
Zn1 N3 C1 C13 -4.6(2) . . . . ?
Zn1 N3 C5 C4 178.09(14) . . . . ?
Zn1 N3 C5 C6 -1.5(2) . . . . ?
Zn1 N4 N5 C8 178.98(14) . . . . ?
Zn1 N4 C6 C5 0.6(2) . . . . ?
Zn1 N4 C6 C7 -179.39(12) . . . . ?
N1 N2 C13 C1 -176.27(16) . . . . ?
N1 N2 C13 C14 0.3(2) . . . . ?
N1 C15 C16 C17 165.02(18) . . . . ?
N1 C15 C16 C18 -76.4(2) . . . . ?
N1 C15 C16 C19 42.8(2) . . . . ?
N2 N1 C15 C14 -1.0(2) . . . . ?
N2 N1 C15 C16 173.31(16) . . . . ?
N2 C13 C14 C15 -0.9(2) . . . . ?
N3 C1 C2 C3 3.6(3) . . . . ?
N3 C1 C13 N2 0.3(2) . . . . ?
N3 C1 C13 C14 -175.44(19) . . . . ?
N3 C5 C6 N4 0.5(2) . . . . ?
N3 C5 C6 C7 -179.44(19) . . . . ?
N4 N5 C8 C7 -0.5(2) . . . . ?
N4 N5 C8 C9 178.83(17) . . . . ?
N4 C6 C7 C8 0.3(2) . . . . ?
N5 N4 C6 C5 179.38(15) . . . . ?
N5 N4 C6 C7 -0.6(2) . . . . ?
N5 C8 C9 C10 175.0(3) . . . . ?
N5 C8 C9 C11 -66.5(3) . . . . ?
N5 C8 C9 C12 52.9(3) . . . . ?
C1 N3 C5 C4 -2.3(3) . . . . ?
C1 N3 C5 C6 178.07(16) . . . . ?
C1 C2 C3 C4 -2.4(3) . . . . ?
C1 C13 C14 C15 175.0(2) . . . . ?
C2 C1 C13 N2 177.35(18) . . . . ?
C2 C1 C13 C14 1.6(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 N3 3.5(3) . . . . ?
C3 C4 C5 C6 -176.97(17) . . . . ?
C4 C5 C6 N4 -179.07(17) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C5 N3 C1 C2 -1.3(3) . . . . ?
C5 N3 C1 C13 175.86(16) . . . . ?
C5 C6 C7 C8 -179.68(19) . . . . ?
C6 N4 N5 C8 0.7(2) . . . . ?
C6 C7 C8 N5 0.1(2) . . . . ?
C6 C7 C8 C9 -179.2(2) . . . . ?
C7 C8 C9 C10 -5.9(4) . . . . ?
C7 C8 C9 C11 112.7(3) . . . . ?
C7 C8 C9 C12 -128.0(2) . . . . ?
C13 C1 C2 C3 -173.23(18) . . . . ?
C13 C14 C15 N1 1.1(2) . . . . ?
C13 C14 C15 C16 -172.48(19) . . . . ?
C14 C15 C16 C17 -22.3(3) . . . . ?
C14 C15 C16 C18 96.3(2) . . . . ?
C14 C15 C16 C19 -144.5(2) . . . . ?
C15 N1 N2 Zn1 -179.52(15) . . . . ?
C15 N1 N2 C13 0.4(2) . . . . ?
