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#$Date: 2022-09-07 01:54:13 +0300 (Wed, 07 Sep 2022) $
#$Revision: 277698 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/11/7711193.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_7711193
loop_
_publ_author_name
'Shekhovtsov, Nikita'
'Nikolaenkova, Elena B.'
'Berezin, Alexey Sergeevich'
'Plyusnin, Victor F.'
'Vinogradova, Katerina A.'
'Naumov, Dmitry Y.'
'Pervukhina, Natalie V.'
'Tikhonov, Alexsei Ya.'
'Bushuev, Mark B.'
_publ_section_title
;
 Tuning ESIPT-coupled luminescence by expanding π-conjugation of a proton
 acceptor moiety in ESIPT-capable zinc(II) complexes with
 1-hydroxy-1H-imidazole-based ligands
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02460H
_journal_year                    2022
_chemical_formula_moiety         'C18 H14 Cl2 N4 O Zn'
_chemical_formula_sum            'C18 H14 Cl2 N4 O Zn'
_chemical_formula_weight         438.60
_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-2017/1
_audit_update_record
;
2022-06-23 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                73.2400(10)
_cell_angle_beta                 85.065(2)
_cell_angle_gamma                69.3580(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7585(4)
_cell_length_b                   8.8124(3)
_cell_length_c                   14.2538(6)
_cell_measurement_reflns_used    3405
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.81
_cell_volume                     873.11(7)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXTL (Bruker, 2004)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6770
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.570
_exptl_absorpt_coefficient_mu    1.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_description       prism
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.6601
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0305
_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)+(0.0427P)²+0.1438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3078
_reflns_number_total             3561
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt02460h2.cif
_cod_data_source_block           mbb_245
_cod_database_code               7711193
_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_min   0.672
_shelx_estimated_absorpt_t_max   0.903
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 -0.07586(4) 0.81815(3) 0.66337(2) 0.02214(10) Uani 1 1 d . . . . .
Cl1 Cl 0.17458(9) 0.87162(7) 0.59828(5) 0.03083(15) Uani 1 1 d . . . . .
Cl2 Cl -0.29392(9) 1.01375(7) 0.71685(5) 0.03292(16) Uani 1 1 d . . . . .
N1 N 0.1686(3) 0.3246(2) 0.85295(14) 0.0202(4) Uani 1 1 d . . . . .
O1 O 0.2698(2) 0.19463(19) 0.92870(12) 0.0276(4) Uani 1 1 d . . . . .
H1 H 0.296806 0.234434 0.969990 0.033 Uiso 1 1 calc R U . . .
N2 N 0.0184(2) 0.5782(2) 0.76268(13) 0.0191(4) Uani 1 1 d . . . . .
N3 N 0.2601(3) 0.4403(2) 0.99575(14) 0.0214(4) Uani 1 1 d . . . . .
N4 N -0.1717(2) 0.6907(2) 0.59232(14) 0.0199(4) Uani 1 1 d . . . . .
C1 C 0.1045(3) 0.2998(3) 0.77473(17) 0.0212(5) Uani 1 1 d . . . . .
C2 C 0.0080(3) 0.4607(3) 0.71880(16) 0.0189(5) Uani 1 1 d . . . . .
C3 C 0.1160(3) 0.4929(3) 0.84521(16) 0.0192(5) Uani 1 1 d . . . . .
C4 C 0.1630(3) 0.5565(3) 0.91940(16) 0.0202(5) Uani 1 1 d . . . . .
C5 C 0.1072(3) 0.7326(3) 0.90878(17) 0.0237(5) Uani 1 1 d . . . . .
H5 H 0.033171 0.812551 0.854440 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1632(3) 0.7832(3) 0.97905(18) 0.0274(5) Uani 1 1 d . . . . .
H6 H 0.129805 0.900263 0.972961 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2698(3) 0.6644(3) 1.06042(17) 0.0246(5) Uani 1 1 d . . . . .
C8 C 0.3136(3) 0.4901(3) 1.06792(17) 0.0228(5) Uani 1 1 d . . . . .
C9 C 0.3338(3) 0.7102(3) 1.13491(19) 0.0309(6) Uani 1 1 d . . . . .
H9 H 0.307256 0.825781 1.130632 0.037 Uiso 1 1 calc R U . . .
C10 C 0.4341(3) 0.5868(4) 1.21317(19) 0.0346(6) Uani 1 1 d . . . . .
H10 H 0.477215 0.617720 1.262813 0.042 Uiso 1 1 calc R U . . .
C11 C 0.4738(3) 0.4154(4) 1.22058(19) 0.0343(6) Uani 1 1 d . . . . .
H11 H 0.541837 0.331753 1.275714 0.041 Uiso 1 1 calc R U . . .
C12 C 0.4157(3) 0.3671(3) 1.14952(18) 0.0289(5) Uani 1 1 d . . . . .
H12 H 0.444311 0.250720 1.155236 0.035 Uiso 1 1 calc R U . . .
C13 C -0.1055(3) 0.5200(3) 0.63007(16) 0.0199(5) Uani 1 1 d . . . . .
C14 C -0.1528(3) 0.4157(3) 0.58709(17) 0.0223(5) Uani 1 1 d . . . . .
H14 H -0.104476 0.296520 0.612837 0.027 Uiso 1 1 calc R U . . .
C15 C -0.2711(3) 0.4890(3) 0.50639(17) 0.0248(5) Uani 1 1 d . . . . .
H15 H -0.303340 0.419984 0.475758 0.030 Uiso 1 1 calc R U . . .
C16 C -0.3419(3) 0.6621(3) 0.47061(18) 0.0265(5) Uani 1 1 d . . . . .
H16 H -0.425928 0.713821 0.416481 0.032 Uiso 1 1 calc R U . . .
C17 C -0.2880(3) 0.7593(3) 0.51514(17) 0.0235(5) Uani 1 1 d . . . . .
H17 H -0.335279 0.878638 0.490012 0.028 Uiso 1 1 calc R U . . .
C18 C 0.1453(4) 0.1274(3) 0.76329(19) 0.0296(6) Uani 1 1 d . . . . .
H18C H 0.245539 0.046344 0.808584 0.044 Uiso 1 1 calc R U . . .
H18B H 0.182262 0.127227 0.695814 0.044 Uiso 1 1 calc R U . . .
H18A H 0.034981 0.095570 0.777973 0.044 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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
N4 Zn1 N2 81.06(7) . . ?
N4 Zn1 Cl2 114.50(6) . . ?
N2 Zn1 Cl2 115.84(5) . . ?
N4 Zn1 Cl1 114.26(5) . . ?
N2 Zn1 Cl1 105.99(5) . . ?
Cl2 Zn1 Cl1 118.91(3) . . ?
C1 N1 C3 110.58(18) . . ?
C1 N1 O1 123.23(17) . . ?
C3 N1 O1 126.18(18) . . ?
N1 O1 H1 109.5 . . ?
C3 N2 C2 107.05(17) . . ?
C3 N2 Zn1 142.10(14) . . ?
C2 N2 Zn1 109.15(14) . . ?
C4 N3 C8 119.28(19) . . ?
C17 N4 C13 119.45(18) . . ?
C17 N4 Zn1 126.50(15) . . ?
C13 N4 Zn1 114.05(14) . . ?
N1 C1 C2 104.19(18) . . ?
N1 C1 C18 121.9(2) . . ?
C2 C1 C18 133.9(2) . . ?
C1 C2 N2 109.85(19) . . ?
C1 C2 C13 131.41(19) . . ?
N2 C2 C13 118.59(18) . . ?
N2 C3 N1 108.32(18) . . ?
N2 C3 C4 129.10(19) . . ?
N1 C3 C4 122.6(2) . . ?
N3 C4 C5 123.1(2) . . ?
N3 C4 C3 115.70(19) . . ?
C5 C4 C3 121.2(2) . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C9 123.2(2) . . ?
C6 C7 C8 117.8(2) . . ?
C9 C7 C8 119.0(2) . . ?
N3 C8 C12 119.5(2) . . ?
N3 C8 C7 120.9(2) . . ?
C12 C8 C7 119.6(2) . . ?
C10 C9 C7 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C7 C9 H9 120.1 . . ?
C9 C10 C11 120.7(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C8 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C8 C12 H12 120.0 . . ?
N4 C13 C14 120.7(2) . . ?
N4 C13 C2 114.51(18) . . ?
C14 C13 C2 124.7(2) . . ?
C15 C14 C13 118.9(2) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 118.7(2) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N4 C17 C16 122.3(2) . . ?
N4 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C1 C18 H18C 109.5 . . ?
C1 C18 H18B 109.5 . . ?
H18C C18 H18B 109.5 . . ?
C1 C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
H18B C18 H18A 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 N4 2.0526(18) . ?
Zn1 N2 2.0908(18) . ?
Zn1 Cl2 2.2124(6) . ?
Zn1 Cl1 2.2229(7) . ?
N1 C1 1.360(3) . ?
N1 C3 1.366(3) . ?
N1 O1 1.376(2) . ?
O1 H1 0.8400 . ?
N2 C3 1.329(3) . ?
N2 C2 1.382(3) . ?
N3 C4 1.325(3) . ?
N3 C8 1.373(3) . ?
N4 C17 1.339(3) . ?
N4 C13 1.361(3) . ?
C1 C2 1.382(3) . ?
C1 C18 1.493(3) . ?
C2 C13 1.461(3) . ?
C3 C4 1.455(3) . ?
C4 C5 1.422(3) . ?
C5 C6 1.364(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.407(3) . ?
C6 H6 0.9500 . ?
C7 C9 1.419(3) . ?
C7 C8 1.425(3) . ?
C8 C12 1.408(3) . ?
C9 C10 1.373(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.368(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.399(3) . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18C 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18A 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
C3 N1 C1 C2 -0.7(2) . . . . ?
O1 N1 C1 C2 178.49(19) . . . . ?
C3 N1 C1 C18 178.6(2) . . . . ?
O1 N1 C1 C18 -2.2(3) . . . . ?
N1 C1 C2 N2 1.1(2) . . . . ?
C18 C1 C2 N2 -178.1(2) . . . . ?
N1 C1 C2 C13 -174.4(2) . . . . ?
C18 C1 C2 C13 6.4(4) . . . . ?
C3 N2 C2 C1 -1.2(2) . . . . ?
Zn1 N2 C2 C1 167.43(15) . . . . ?
C3 N2 C2 C13 174.99(19) . . . . ?
Zn1 N2 C2 C13 -16.4(2) . . . . ?
C2 N2 C3 N1 0.7(2) . . . . ?
Zn1 N2 C3 N1 -161.59(18) . . . . ?
C2 N2 C3 C4 -178.3(2) . . . . ?
Zn1 N2 C3 C4 19.4(4) . . . . ?
C1 N1 C3 N2 0.0(3) . . . . ?
O1 N1 C3 N2 -179.15(19) . . . . ?
C1 N1 C3 C4 179.1(2) . . . . ?
O1 N1 C3 C4 -0.1(3) . . . . ?
C8 N3 C4 C5 -1.2(3) . . . . ?
C8 N3 C4 C3 178.52(19) . . . . ?
N2 C3 C4 N3 178.7(2) . . . . ?
N1 C3 C4 N3 -0.2(3) . . . . ?
N2 C3 C4 C5 -1.6(4) . . . . ?
N1 C3 C4 C5 179.6(2) . . . . ?
N3 C4 C5 C6 2.7(3) . . . . ?
C3 C4 C5 C6 -177.1(2) . . . . ?
C4 C5 C6 C7 -1.2(4) . . . . ?
C5 C6 C7 C9 179.1(2) . . . . ?
C5 C6 C7 C8 -1.3(4) . . . . ?
C4 N3 C8 C12 179.5(2) . . . . ?
C4 N3 C8 C7 -1.5(3) . . . . ?
C6 C7 C8 N3 2.8(3) . . . . ?
C9 C7 C8 N3 -177.6(2) . . . . ?
C6 C7 C8 C12 -178.3(2) . . . . ?
C9 C7 C8 C12 1.3(3) . . . . ?
C6 C7 C9 C10 178.7(2) . . . . ?
C8 C7 C9 C10 -0.8(4) . . . . ?
C7 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C8 -0.5(4) . . . . ?
N3 C8 C12 C11 178.3(2) . . . . ?
C7 C8 C12 C11 -0.6(3) . . . . ?
C17 N4 C13 C14 2.2(3) . . . . ?
Zn1 N4 C13 C14 -177.52(16) . . . . ?
C17 N4 C13 C2 -175.3(2) . . . . ?
Zn1 N4 C13 C2 5.1(2) . . . . ?
C1 C2 C13 N4 -176.6(2) . . . . ?
N2 C2 C13 N4 8.2(3) . . . . ?
C1 C2 C13 C14 6.1(4) . . . . ?
N2 C2 C13 C14 -169.1(2) . . . . ?
N4 C13 C14 C15 -1.2(3) . . . . ?
C2 C13 C14 C15 175.9(2) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 1.8(3) . . . . ?
C13 N4 C17 C16 -1.1(3) . . . . ?
Zn1 N4 C17 C16 178.52(17) . . . . ?
C15 C16 C17 N4 -0.9(4) . . . . ?
