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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/7/71/11/7711194.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_7711194
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_sum            'C18 H14 I2 N4 O Zn'
_chemical_formula_weight         621.50
_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_method           SHELXL-2017/1
_audit_update_record
;
2022-06-21 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                93.867(2)
_cell_angle_beta                 99.890(2)
_cell_angle_gamma                111.278(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8596(3)
_cell_length_b                   8.1625(3)
_cell_length_c                   16.6942(7)
_cell_measurement_reflns_used    6141
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.87
_cell_measurement_theta_min      2.50
_cell_volume                     973.29(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0465
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17112
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.502
_exptl_absorpt_coefficient_mu    4.448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_density_diffrn    2.121
_exptl_crystal_description       prism
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.7459
_exptl_transmission_factor_min   0.6590
_refine_diff_density_max         1.265
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0309
_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)+(0.0384P)²+0.0687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3384
_reflns_number_total             3984
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt02460h2.cif
_cod_data_source_block           345
_cod_database_code               7711194
_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   0.403
_shelx_estimated_absorpt_t_max   0.717
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 0.31052(6) 0.24782(6) 0.32124(3) 0.02462(13) Uani 1 1 d . . . . .
I1 I 0.30567(4) 0.53909(4) 0.38186(2) 0.03158(10) Uani 1 1 d . . . . .
I2 I 0.59840(4) 0.23071(4) 0.27597(2) 0.03151(10) Uani 1 1 d . . . . .
N1 N -0.1981(5) -0.0400(5) 0.1510(2) 0.0246(7) Uani 1 1 d . . . . .
N2 N 0.0670(5) 0.1008(4) 0.2378(2) 0.0236(7) Uani 1 1 d . . . . .
N3 N -0.0901(5) 0.1470(4) 0.0265(2) 0.0246(7) Uani 1 1 d . . . . .
N4 N 0.1990(5) 0.0537(5) 0.3906(2) 0.0268(8) Uani 1 1 d . . . . .
O1 O -0.3366(4) -0.0921(4) 0.08104(19) 0.0315(7) Uani 1 1 d . . . . .
H1 H -0.293(8) -0.032(7) 0.045(3) 0.047 Uiso 1 1 d . U . . .
C1 C -0.2169(6) -0.1221(5) 0.2188(3) 0.0258(9) Uani 1 1 d . . . . .
C2 C -0.0469(5) -0.0326(5) 0.2734(2) 0.0217(8) Uani 1 1 d . . . . .
C3 C -0.0268(6) 0.0917(5) 0.1626(2) 0.0235(9) Uani 1 1 d . . . . .
C4 C 0.0331(6) 0.1956(5) 0.0975(3) 0.0241(9) Uani 1 1 d . . . . .
C5 C 0.2097(6) 0.3365(6) 0.1093(3) 0.0272(9) Uani 1 1 d . . . . .
H5 H 0.295797 0.366631 0.160582 0.033 Uiso 1 1 calc R U . . .
C6 C 0.2536(6) 0.4286(6) 0.0450(3) 0.0286(9) Uani 1 1 d . . . . .
H6 H 0.370766 0.524493 0.051765 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1252(6) 0.3812(6) -0.0310(3) 0.0253(9) Uani 1 1 d . . . . .
C8 C -0.0474(6) 0.2360(5) -0.0387(3) 0.0243(9) Uani 1 1 d . . . . .
C9 C 0.1596(6) 0.4695(6) -0.0997(3) 0.0286(9) Uani 1 1 d . . . . .
H9 H 0.274060 0.567414 -0.095508 0.034 Uiso 1 1 calc R U . . .
C10 C 0.0300(7) 0.4162(6) -0.1727(3) 0.0336(10) Uani 1 1 d . . . . .
H10 H 0.053828 0.478606 -0.218178 0.040 Uiso 1 1 calc R U . . .
C11 C -0.1377(6) 0.2689(6) -0.1797(3) 0.0303(10) Uani 1 1 d . . . . .
H11 H -0.224916 0.230074 -0.230776 0.036 Uiso 1 1 calc R U . . .
C12 C -0.1780(6) 0.1801(6) -0.1140(3) 0.0283(9) Uani 1 1 d . . . . .
H12 H -0.292892 0.081954 -0.119342 0.034 Uiso 1 1 calc R U . . .
C13 C 0.0257(6) -0.0653(5) 0.3547(3) 0.0250(9) Uani 1 1 d . . . . .
C14 C -0.0668(7) -0.2062(6) 0.3929(3) 0.0352(11) Uani 1 1 d . . . . .
H14 H -0.187413 -0.289357 0.366591 0.042 Uiso 1 1 calc R U . . .
C15 C 0.0175(7) -0.2256(7) 0.4699(3) 0.0372(11) Uani 1 1 d . . . . .
H15 H -0.044113 -0.322129 0.496761 0.045 Uiso 1 1 calc R U . . .
C16 C 0.1926(7) -0.1018(7) 0.5066(3) 0.0375(11) Uani 1 1 d . . . . .
H16 H 0.252787 -0.111090 0.559580 0.045 Uiso 1 1 calc R U . . .
C17 C 0.2795(6) 0.0364(6) 0.4650(3) 0.0310(10) Uani 1 1 d . . . . .
H17 H 0.400085 0.121226 0.490319 0.037 Uiso 1 1 calc R U . . .
C18 C -0.3907(6) -0.2708(6) 0.2240(3) 0.0326(10) Uani 1 1 d . . . . .
H18A H -0.373416 -0.383366 0.216075 0.049 Uiso 1 1 calc R U . . .
H18B H -0.493975 -0.272352 0.181306 0.049 Uiso 1 1 calc R U . . .
H18C H -0.419463 -0.254983 0.278162 0.049 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'
I I -0.4742 1.8119 '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
N4 Zn1 N2 81.83(14) . . ?
N4 Zn1 I1 109.60(10) . . ?
N2 Zn1 I1 111.64(9) . . ?
N4 Zn1 I2 112.64(10) . . ?
N2 Zn1 I2 112.43(10) . . ?
I1 Zn1 I2 121.74(2) . . ?
C3 N1 C1 110.5(3) . . ?
C3 N1 O1 127.0(3) . . ?
C1 N1 O1 122.5(3) . . ?
C3 N2 C2 106.8(3) . . ?
C3 N2 Zn1 143.1(3) . . ?
C2 N2 Zn1 110.0(3) . . ?
C4 N3 C8 119.5(4) . . ?
C17 N4 C13 119.2(4) . . ?
C17 N4 Zn1 126.6(3) . . ?
C13 N4 Zn1 114.2(3) . . ?
N1 O1 H1 108(4) . . ?
N1 C1 C2 104.1(4) . . ?
N1 C1 C18 122.5(4) . . ?
C2 C1 C18 133.4(4) . . ?
N2 C2 C1 109.5(4) . . ?
N2 C2 C13 119.3(4) . . ?
C1 C2 C13 131.0(4) . . ?
N2 C3 N1 109.0(4) . . ?
N2 C3 C4 129.2(4) . . ?
N1 C3 C4 121.7(4) . . ?
N3 C4 C5 122.7(4) . . ?
N3 C4 C3 114.9(4) . . ?
C5 C4 C3 122.4(4) . . ?
C6 C5 C4 118.5(4) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C7 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C9 123.6(4) . . ?
C6 C7 C8 118.1(4) . . ?
C9 C7 C8 118.4(4) . . ?
N3 C8 C12 118.7(4) . . ?
N3 C8 C7 121.0(4) . . ?
C12 C8 C7 120.3(4) . . ?
C10 C9 C7 121.1(4) . . ?
C10 C9 H9 119.5 . . ?
C7 C9 H9 119.5 . . ?
C9 C10 C11 119.6(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C8 119.3(4) . . ?
C11 C12 H12 120.3 . . ?
C8 C12 H12 120.3 . . ?
N4 C13 C14 121.2(4) . . ?
N4 C13 C2 114.0(4) . . ?
C14 C13 C2 124.7(4) . . ?
C13 C14 C15 119.7(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 118.7(5) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 119.1(4) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
N4 C17 C16 122.1(4) . . ?
N4 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C1 C18 H18A 109.5 . . ?
C1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 2.051(4) . ?
Zn1 N2 2.058(3) . ?
Zn1 I1 2.5362(6) . ?
Zn1 I2 2.5520(5) . ?
N1 C3 1.355(5) . ?
N1 C1 1.356(5) . ?
N1 O1 1.375(4) . ?
N2 C3 1.325(5) . ?
N2 C2 1.380(5) . ?
N3 C4 1.328(5) . ?
N3 C8 1.371(5) . ?
N4 C17 1.335(5) . ?
N4 C13 1.356(5) . ?
O1 H1 0.84(6) . ?
C1 C2 1.391(6) . ?
C1 C18 1.483(6) . ?
C2 C13 1.460(6) . ?
C3 C4 1.460(6) . ?
C4 C5 1.416(6) . ?
C5 C6 1.373(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.411(6) . ?
C6 H6 0.9500 . ?
C7 C9 1.407(6) . ?
C7 C8 1.419(6) . ?
C8 C12 1.408(6) . ?
C9 C10 1.376(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.381(6) . ?
C14 C15 1.388(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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 0.2(4) . . . . ?
O1 N1 C1 C2 178.7(3) . . . . ?
C3 N1 C1 C18 179.5(4) . . . . ?
O1 N1 C1 C18 -2.0(6) . . . . ?
C3 N2 C2 C1 -1.7(4) . . . . ?
Zn1 N2 C2 C1 175.3(3) . . . . ?
C3 N2 C2 C13 174.8(3) . . . . ?
Zn1 N2 C2 C13 -8.3(4) . . . . ?
N1 C1 C2 N2 0.9(4) . . . . ?
C18 C1 C2 N2 -178.3(4) . . . . ?
N1 C1 C2 C13 -175.0(4) . . . . ?
C18 C1 C2 C13 5.8(8) . . . . ?
C2 N2 C3 N1 1.8(4) . . . . ?
Zn1 N2 C3 N1 -173.5(3) . . . . ?
C2 N2 C3 C4 -176.3(4) . . . . ?
Zn1 N2 C3 C4 8.5(8) . . . . ?
C1 N1 C3 N2 -1.3(5) . . . . ?
O1 N1 C3 N2 -179.7(3) . . . . ?
C1 N1 C3 C4 177.0(4) . . . . ?
O1 N1 C3 C4 -1.4(6) . . . . ?
C8 N3 C4 C5 -0.4(6) . . . . ?
C8 N3 C4 C3 -180.0(3) . . . . ?
N2 C3 C4 N3 175.9(4) . . . . ?
N1 C3 C4 N3 -2.0(6) . . . . ?
N2 C3 C4 C5 -3.7(7) . . . . ?
N1 C3 C4 C5 178.4(4) . . . . ?
N3 C4 C5 C6 1.2(6) . . . . ?
C3 C4 C5 C6 -179.2(4) . . . . ?
C4 C5 C6 C7 -0.7(6) . . . . ?
C5 C6 C7 C9 179.7(4) . . . . ?
C5 C6 C7 C8 -0.6(6) . . . . ?
C4 N3 C8 C12 178.6(4) . . . . ?
C4 N3 C8 C7 -1.0(6) . . . . ?
C6 C7 C8 N3 1.5(6) . . . . ?
C9 C7 C8 N3 -178.8(4) . . . . ?
C6 C7 C8 C12 -178.1(4) . . . . ?
C9 C7 C8 C12 1.5(6) . . . . ?
C6 C7 C9 C10 179.2(4) . . . . ?
C8 C7 C9 C10 -0.4(6) . . . . ?
C7 C9 C10 C11 -1.4(6) . . . . ?
C9 C10 C11 C12 2.2(7) . . . . ?
C10 C11 C12 C8 -1.0(6) . . . . ?
N3 C8 C12 C11 179.5(4) . . . . ?
C7 C8 C12 C11 -0.8(6) . . . . ?
C17 N4 C13 C14 -1.6(6) . . . . ?
Zn1 N4 C13 C14 178.6(3) . . . . ?
C17 N4 C13 C2 -179.8(4) . . . . ?
Zn1 N4 C13 C2 0.4(4) . . . . ?
N2 C2 C13 N4 5.5(5) . . . . ?
C1 C2 C13 N4 -179.0(4) . . . . ?
N2 C2 C13 C14 -172.7(4) . . . . ?
C1 C2 C13 C14 2.9(7) . . . . ?
N4 C13 C14 C15 0.9(7) . . . . ?
C2 C13 C14 C15 178.9(4) . . . . ?
C13 C14 C15 C16 0.3(7) . . . . ?
C14 C15 C16 C17 -0.8(7) . . . . ?
C13 N4 C17 C16 1.1(6) . . . . ?
Zn1 N4 C17 C16 -179.2(3) . . . . ?
C15 C16 C17 N4 0.1(7) . . . . ?
