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#$Date: 2024-09-06 03:38:21 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294539 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/67/7716714.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_7716714
loop_
_publ_author_name
'Savić, Milica'
'Pevec, Andrej'
'Stevanović, Nevena'
'Novaković, Irena'
'Matić, Ivana Z'
'Petrović, Nina'
'Stanojković, Tatjana'
'Milčić, Karla'
'Zlatar, Matija'
'Turel, Iztok'
'Čobeljić, Božidar'
'Milčić, Miloš'
'Gruden, Maja'
_publ_section_title
;
 Synergy of experimental and computational chemistry: structure and
 biological activity of Zn(II) hydrazone complexes.
;
_journal_issue                   32
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13436
_journal_page_last               13453
_journal_paper_doi               10.1039/d4dt01353k
_journal_volume                  53
_journal_year                    2024
_chemical_formula_sum            'C14 H17 Br N6 O3 Zn'
_chemical_formula_weight         462.61
_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   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-03-13 deposited with the CCDC.	2024-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                95.579(4)
_cell_angle_beta                 92.748(4)
_cell_angle_gamma                110.231(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4852(3)
_cell_length_b                   9.8974(5)
_cell_length_c                   13.2682(6)
_cell_measurement_reflns_used    4902
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.6080
_cell_measurement_theta_min      2.8770
_cell_volume                     914.44(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10782
_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         27.476
_diffrn_reflns_theta_min         2.848
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.553
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         2.296
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0915P)²+2.0301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1596
_refine_ls_wR_factor_ref         0.1735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3284
_reflns_number_total             4195
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt01353k2.cif
_cod_data_source_block           '[ZnL(OCN)2]'
_cod_depositor_comments
'Adding full bibliography for 7716713--7716715.cif.'
_cod_database_code               7716714
_shelx_shelxl_version_number     2018/3
_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   0.270
_shelx_estimated_absorpt_t_max   0.718
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 0.78962(8) 0.64909(6) 0.73803(4) 0.03207(19) Uani 1 1 d . . . . .
Br1 Br 1.12538(8) 0.90461(5) 0.59082(4) 0.0440(2) Uani 1 1 d . . . . .
N1 N 0.8558(5) 0.6298(4) 0.5694(3) 0.0249(8) Uani 1 1 d . . . . .
N2 N 0.6273(5) 0.4418(4) 0.6750(3) 0.0235(7) Uani 1 1 d . . . . .
N3 N 0.5158(5) 0.3496(4) 0.7377(3) 0.0268(8) Uani 1 1 d . . . . .
N4 N 0.3304(7) 0.1800(4) 0.8987(3) 0.0365(10) Uani 1 1 d . . . . .
O1 O 0.6474(7) 0.5474(4) 0.8609(3) 0.0558(12) Uani 1 1 d . . . . .
C1 C 0.9648(6) 0.7252(5) 0.5163(4) 0.0271(9) Uani 1 1 d . . . . .
C2 C 0.9787(7) 0.7066(5) 0.4123(4) 0.0302(10) Uani 1 1 d . . . . .
H2 H 1.062725 0.780447 0.378601 0.036 Uiso 1 1 calc R U . . .
C3 C 0.8641(7) 0.5755(5) 0.3609(3) 0.0302(10) Uani 1 1 d . . . . .
H3 H 0.865458 0.557165 0.289360 0.036 Uiso 1 1 calc R U . . .
C4 C 0.7456(6) 0.4695(5) 0.4141(3) 0.0281(9) Uani 1 1 d . . . . .
H4 H 0.666867 0.378007 0.379443 0.034 Uiso 1 1 calc R U . . .
C5 C 0.7445(6) 0.4995(5) 0.5185(3) 0.0230(8) Uani 1 1 d . . . . .
C6 C 0.6228(6) 0.3936(5) 0.5817(3) 0.0241(9) Uani 1 1 d . . . . .
C7 C 0.5067(7) 0.2416(5) 0.5369(4) 0.0323(10) Uani 1 1 d . . . . .
H7A H 0.512725 0.174253 0.585367 0.048 Uiso 1 1 calc R U . . .
H7B H 0.557944 0.217604 0.473799 0.048 Uiso 1 1 calc R U . . .
H7C H 0.373572 0.233507 0.522404 0.048 Uiso 1 1 calc R U . . .
C8 C 0.5415(7) 0.4181(5) 0.8307(3) 0.0313(10) Uani 1 1 d . . . . .
C9 C 0.4344(8) 0.3406(5) 0.9146(4) 0.0372(12) Uani 1 1 d . . . . .
H9A H 0.527518 0.361592 0.974720 0.045 Uiso 1 1 calc R U . . .
H9B H 0.339956 0.386283 0.932872 0.045 Uiso 1 1 calc R U . . .
C10 C 0.4484(16) 0.0975(10) 0.8629(7) 0.097(4) Uani 1 1 d . . . . .
H10A H 0.565908 0.126018 0.908330 0.146 Uiso 1 1 calc R U . . .
H10B H 0.481039 0.117525 0.793913 0.146 Uiso 1 1 calc R U . . .
H10C H 0.377496 -0.006420 0.862507 0.146 Uiso 1 1 calc R U . . .
C11 C 0.1615(11) 0.1431(8) 0.8237(5) 0.074(3) Uani 1 1 d . . . . .
H11A H 0.204247 0.171506 0.757730 0.111 Uiso 1 1 calc R U . . .
H11B H 0.078269 0.195157 0.847259 0.111 Uiso 1 1 calc R U . . .
H11C H 0.090702 0.038398 0.816745 0.111 Uiso 1 1 calc R U . . .
C12 C 0.2592(9) 0.1368(6) 0.9979(4) 0.0445(13) Uani 1 1 d . . . . .
H12A H 0.203234 0.030793 0.993004 0.067 Uiso 1 1 calc R U . . .
H12B H 0.161834 0.178617 1.015015 0.067 Uiso 1 1 calc R U . . .
H12C H 0.365749 0.172544 1.051056 0.067 Uiso 1 1 calc R U . . .
N5 N 0.6948(7) 0.8080(5) 0.7338(3) 0.0421(10) Uani 1 1 d . . . . .
C13 C 0.7065(7) 0.9224(6) 0.7163(4) 0.0352(11) Uani 1 1 d . . . . .
O2 O 0.7134(7) 1.0405(5) 0.6993(4) 0.0705(15) Uani 1 1 d . . . . .
N6 N 1.0463(7) 0.6993(6) 0.8050(4) 0.0552(14) Uani 1 1 d . . . . .
C14A C 1.149(3) 0.7339(14) 0.8706(13) 0.049(4) Uani 0.581(17) 1 d . . P A 1
O3A O 1.2560(17) 0.7717(13) 0.9459(8) 0.101(5) Uani 0.581(17) 1 d . . P A 1
C14B C 1.146(3) 0.671(3) 0.8506(16) 0.054(5) Uani 0.419(17) 1 d . . P A 2
O3B O 1.263(3) 0.622(3) 0.8874(17) 0.148(11) Uani 0.419(17) 1 d . . 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 0.0033 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'
Br Br -0.2901 2.4595 '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
N5 Zn1 N6 115.9(2) . . ?
N5 Zn1 N2 121.31(18) . . ?
N6 Zn1 N2 122.8(2) . . ?
N5 Zn1 O1 101.01(19) . . ?
N6 Zn1 O1 94.7(2) . . ?
N2 Zn1 O1 75.31(14) . . ?
N5 Zn1 N1 97.37(16) . . ?
N6 Zn1 N1 99.9(2) . . ?
N2 Zn1 N1 73.41(14) . . ?
O1 Zn1 N1 148.61(14) . . ?
C1 N1 C5 117.3(4) . . ?
C1 N1 Zn1 131.0(3) . . ?
C5 N1 Zn1 111.3(3) . . ?
C6 N2 N3 118.2(4) . . ?
C6 N2 Zn1 124.1(3) . . ?
N3 N2 Zn1 117.7(3) . . ?
C8 N3 N2 109.2(4) . . ?
C10 N4 C11 108.1(7) . . ?
C10 N4 C12 110.1(5) . . ?
C11 N4 C12 107.7(5) . . ?
C10 N4 C9 113.6(6) . . ?
C11 N4 C9 110.2(5) . . ?
C12 N4 C9 106.9(4) . . ?
C8 O1 Zn1 110.4(3) . . ?
N1 C1 C2 126.3(4) . . ?
N1 C1 Br1 116.2(3) . . ?
C2 C1 Br1 117.5(3) . . ?
C3 C2 C1 116.3(4) . . ?
C3 C2 H2 121.9 . . ?
C1 C2 H2 121.9 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 121.3(4) . . ?
N1 C5 C6 115.7(4) . . ?
C4 C5 C6 123.0(4) . . ?
N2 C6 C5 115.2(4) . . ?
N2 C6 C7 123.6(4) . . ?
C5 C6 C7 121.2(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N3 127.4(4) . . ?
O1 C8 C9 112.8(4) . . ?
N3 C8 C9 119.8(4) . . ?
N4 C9 C8 120.5(4) . . ?
N4 C9 H9A 107.2 . . ?
C8 C9 H9A 107.2 . . ?
N4 C9 H9B 107.2 . . ?
C8 C9 H9B 107.2 . . ?
H9A C9 H9B 106.8 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C11 H11A 109.5 . . ?
N4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 N5 Zn1 153.2(4) . . ?
N5 C13 O2 178.0(6) . . ?
C14B N6 Zn1 149.8(15) . . ?
C14A N6 Zn1 153.0(12) . . ?
N6 C14A O3A 177(2) . . ?
N6 C14B O3B 168(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 N5 1.940(5) . ?
Zn1 N6 1.954(5) . ?
Zn1 N2 2.057(4) . ?
Zn1 O1 2.133(4) . ?
Zn1 N1 2.319(4) . ?
Br1 C1 1.909(5) . ?
N1 C1 1.306(6) . ?
N1 C5 1.358(6) . ?
N2 C6 1.277(6) . ?
N2 N3 1.382(5) . ?
N3 C8 1.320(6) . ?
N4 C10 1.462(8) . ?
N4 C11 1.487(8) . ?
N4 C12 1.490(6) . ?
N4 C9 1.497(6) . ?
O1 C8 1.262(6) . ?
C1 C2 1.388(7) . ?
C2 C3 1.374(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.488(6) . ?
C6 C7 1.498(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.516(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
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 . ?
N5 C13 1.153(7) . ?
C13 O2 1.196(7) . ?
N6 C14B 1.07(2) . ?
N6 C14A 1.079(16) . ?
C14A O3A 1.192(17) . ?
C14B O3B 1.24(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
C6 N2 N3 C8 179.2(4) . . . . ?
Zn1 N2 N3 C8 -1.0(5) . . . . ?
C5 N1 C1 C2 -0.2(7) . . . . ?
Zn1 N1 C1 C2 -172.5(3) . . . . ?
C5 N1 C1 Br1 -178.0(3) . . . . ?
Zn1 N1 C1 Br1 9.6(5) . . . . ?
N1 C1 C2 C3 1.0(7) . . . . ?
Br1 C1 C2 C3 178.8(3) . . . . ?
C1 C2 C3 C4 -1.2(7) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C1 N1 C5 C4 -0.4(6) . . . . ?
Zn1 N1 C5 C4 173.4(3) . . . . ?
C1 N1 C5 C6 179.9(4) . . . . ?
Zn1 N1 C5 C6 -6.3(4) . . . . ?
C3 C4 C5 N1 0.1(7) . . . . ?
C3 C4 C5 C6 179.8(4) . . . . ?
N3 N2 C6 C5 179.2(3) . . . . ?
Zn1 N2 C6 C5 -0.5(5) . . . . ?
N3 N2 C6 C7 -1.4(6) . . . . ?
Zn1 N2 C6 C7 178.9(3) . . . . ?
N1 C5 C6 N2 4.9(5) . . . . ?
C4 C5 C6 N2 -174.8(4) . . . . ?
N1 C5 C6 C7 -174.4(4) . . . . ?
C4 C5 C6 C7 5.8(6) . . . . ?
Zn1 O1 C8 N3 -0.2(7) . . . . ?
Zn1 O1 C8 C9 -179.3(4) . . . . ?
N2 N3 C8 O1 0.8(7) . . . . ?
N2 N3 C8 C9 179.8(4) . . . . ?
C10 N4 C9 C8 52.5(7) . . . . ?
C11 N4 C9 C8 -69.0(7) . . . . ?
C12 N4 C9 C8 174.2(5) . . . . ?
O1 C8 C9 N4 -168.7(5) . . . . ?
N3 C8 C9 N4 12.1(8) . . . . ?
Zn1 N6 C14B O3B 74(14) . . . . ?
