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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/7/71/11/7711192.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_7711192
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 Br2 N4 O Zn'
_chemical_formula_weight         527.52
_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                100.5130(10)
_cell_angle_beta                 95.7590(10)
_cell_angle_gamma                116.9750(10)
_cell_formula_units_Z            2
_cell_length_a                   8.61310(10)
_cell_length_b                   8.8588(2)
_cell_length_c                   13.9114(3)
_cell_measurement_reflns_used    6202
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.71
_cell_volume                     909.57(3)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8945
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         26.333
_diffrn_reflns_theta_min         2.670
_exptl_absorpt_coefficient_mu    5.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.5150
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.899
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0191
_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)+(0.0462P)²+0.0055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3353
_reflns_number_total             3650
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt02460h2.cif
_cod_data_source_block           mbb_253
_cod_database_code               7711192
_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   0.339
_shelx_estimated_absorpt_t_max   0.762
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 0.32054(3) 0.24957(2) 0.33508(2) 0.01722(7) Uani 1 1 d . . . . .
Br1 Br 0.31132(2) 0.50852(2) 0.40176(2) 0.02338(7) Uani 1 1 d . . . . .
Br2 Br 0.57198(2) 0.26792(2) 0.27426(2) 0.02472(7) Uani 1 1 d . . . . .
N1 N -0.19626(19) -0.05172(19) 0.15093(11) 0.0170(3) Uani 1 1 d . . . . .
N2 N 0.07538(19) 0.08478(18) 0.23875(11) 0.0158(3) Uani 1 1 d . . . . .
N3 N -0.11034(19) 0.14537(18) 0.01248(11) 0.0174(3) Uani 1 1 d . . . . .
N4 N 0.22185(19) 0.05571(18) 0.40914(11) 0.0164(3) Uani 1 1 d . . . . .
O1 O -0.34134(16) -0.09904(17) 0.07754(10) 0.0240(3) Uani 1 1 d . . . . .
H1 H -0.293(3) -0.020(3) 0.0346(17) 0.036 Uiso 1 1 d . U . . .
C1 C -0.2035(2) -0.1314(2) 0.22599(13) 0.0161(3) Uani 1 1 d . . . . .
C2 C -0.0308(2) -0.0449(2) 0.28080(13) 0.0157(3) Uani 1 1 d . . . . .
C3 C -0.0268(2) 0.0789(2) 0.15885(13) 0.0159(3) Uani 1 1 d . . . . .
C4 C 0.0214(2) 0.1838(2) 0.08679(13) 0.0169(4) Uani 1 1 d . . . . .
C5 C 0.1986(2) 0.3164(2) 0.09655(13) 0.0193(4) Uani 1 1 d . . . . .
H5 H 0.288641 0.337545 0.148475 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2334(2) 0.4126(2) 0.02735(14) 0.0207(4) Uani 1 1 d . . . . .
H6 H 0.348666 0.500996 0.032296 0.025 Uiso 1 1 calc R U . . .
C7 C 0.0972(2) 0.3793(2) -0.05096(13) 0.0179(4) Uani 1 1 d . . . . .
C8 C -0.0767(2) 0.2395(2) -0.05744(13) 0.0171(4) Uani 1 1 d . . . . .
C9 C 0.1241(3) 0.4768(2) -0.12395(14) 0.0217(4) Uani 1 1 d . . . . .
H9 H 0.236087 0.570055 -0.119847 0.026 Uiso 1 1 calc R U . . .
C10 C -0.0130(3) 0.4349(2) -0.20005(14) 0.0250(4) Uani 1 1 d . . . . .
H10 H 0.005865 0.499561 -0.247457 0.030 Uiso 1 1 calc R U . . .
C11 C -0.1837(3) 0.2934(3) -0.20706(14) 0.0239(4) Uani 1 1 d . . . . .
H11 H -0.275593 0.264362 -0.260029 0.029 Uiso 1 1 calc R U . . .
C12 C -0.2157(2) 0.1986(2) -0.13722(14) 0.0217(4) Uani 1 1 d . . . . .
H12 H -0.329266 0.107063 -0.142281 0.026 Uiso 1 1 calc R U . . .
C13 C 0.0512(2) -0.0694(2) 0.36942(13) 0.0157(3) Uani 1 1 d . . . . .
C14 C -0.0321(2) -0.2123(2) 0.41016(14) 0.0195(4) Uani 1 1 d . . . . .
H14 H -0.149989 -0.297120 0.383193 0.023 Uiso 1 1 calc R U . . .
C15 C 0.0633(3) -0.2256(2) 0.49079(14) 0.0227(4) Uani 1 1 d . . . . .
H15 H 0.010135 -0.320097 0.518491 0.027 Uiso 1 1 calc R U . . .
C16 C 0.2386(3) -0.0976(2) 0.53059(14) 0.0232(4) Uani 1 1 d . . . . .
H16 H 0.304939 -0.105025 0.584807 0.028 Uiso 1 1 calc R U . . .
C17 C 0.3120(2) 0.0405(2) 0.48780(13) 0.0198(4) Uani 1 1 d . . . . .
H17 H 0.429212 0.127131 0.514608 0.024 Uiso 1 1 calc R U . . .
C18 C -0.3736(2) -0.2783(2) 0.23562(15) 0.0223(4) Uani 1 1 d . . . . .
H18A H -0.382518 -0.263380 0.304588 0.033 Uiso 1 1 calc R U . . .
H18B H -0.375199 -0.387719 0.211352 0.033 Uiso 1 1 calc R U . . .
H18C H -0.472501 -0.278197 0.197094 0.033 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'
Br Br -0.2901 2.4595 '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 80.94(6) . . ?
N4 Zn1 Br2 112.28(4) . . ?
N2 Zn1 Br2 116.27(4) . . ?
N4 Zn1 Br1 116.35(4) . . ?
N2 Zn1 Br1 105.27(4) . . ?
Br2 Zn1 Br1 119.372(10) . . ?
C1 N1 C3 110.60(15) . . ?
C1 N1 O1 123.59(14) . . ?
C3 N1 O1 125.80(15) . . ?
C3 N2 C2 107.36(14) . . ?
C3 N2 Zn1 140.75(12) . . ?
C2 N2 Zn1 110.34(11) . . ?
C4 N3 C8 119.23(15) . . ?
C17 N4 C13 119.17(15) . . ?
C17 N4 Zn1 126.33(12) . . ?
C13 N4 Zn1 114.44(12) . . ?
N1 O1 H1 104.0(13) . . ?
N1 C1 C2 104.28(14) . . ?
N1 C1 C18 121.72(16) . . ?
C2 C1 C18 134.00(17) . . ?
N2 C2 C1 109.67(16) . . ?
N2 C2 C13 118.42(15) . . ?
C1 C2 C13 131.90(16) . . ?
N2 C3 N1 108.08(15) . . ?
N2 C3 C4 129.24(15) . . ?
N1 C3 C4 122.66(16) . . ?
N3 C4 C5 123.24(16) . . ?
N3 C4 C3 115.60(15) . . ?
C5 C4 C3 121.16(16) . . ?
C6 C5 C4 117.97(17) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C7 120.66(17) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C9 123.34(17) . . ?
C6 C7 C8 117.93(16) . . ?
C9 C7 C8 118.73(17) . . ?
N3 C8 C12 119.64(16) . . ?
N3 C8 C7 120.91(16) . . ?
C12 C8 C7 119.45(16) . . ?
C10 C9 C7 120.54(18) . . ?
C10 C9 H9 119.7 . . ?
C7 C9 H9 119.7 . . ?
C9 C10 C11 120.21(17) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 121.01(18) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C8 120.04(17) . . ?
C11 C12 H12 120.0 . . ?
C8 C12 H12 120.0 . . ?
N4 C13 C14 120.83(16) . . ?
N4 C13 C2 114.56(15) . . ?
C14 C13 C2 124.56(16) . . ?
C15 C14 C13 118.98(17) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 119.87(17) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 118.26(18) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
N4 C17 C16 122.88(17) . . ?
N4 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
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 2.0568(14) . ?
Zn1 N2 2.0755(15) . ?
Zn1 Br2 2.3518(3) . ?
Zn1 Br1 2.3522(3) . ?
N1 C1 1.354(2) . ?
N1 C3 1.368(2) . ?
N1 O1 1.3756(19) . ?
N2 C3 1.324(2) . ?
N2 C2 1.378(2) . ?
N3 C4 1.326(2) . ?
N3 C8 1.364(2) . ?
N4 C17 1.340(2) . ?
N4 C13 1.353(2) . ?
O1 H1 0.98(2) . ?
C1 C2 1.381(2) . ?
C1 C18 1.494(2) . ?
C2 C13 1.458(2) . ?
C3 C4 1.454(2) . ?
C4 C5 1.415(2) . ?
C5 C6 1.367(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9300 . ?
C7 C9 1.420(3) . ?
C7 C8 1.426(3) . ?
C8 C12 1.410(2) . ?
C9 C10 1.364(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.413(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.400(2) . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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 -0.24(18) . . . . ?
O1 N1 C1 C2 179.45(14) . . . . ?
C3 N1 C1 C18 179.55(15) . . . . ?
O1 N1 C1 C18 -0.8(2) . . . . ?
C3 N2 C2 C1 -0.84(18) . . . . ?
Zn1 N2 C2 C1 168.00(10) . . . . ?
C3 N2 C2 C13 178.55(13) . . . . ?
Zn1 N2 C2 C13 -12.60(18) . . . . ?
N1 C1 C2 N2 0.66(17) . . . . ?
C18 C1 C2 N2 -179.10(18) . . . . ?
N1 C1 C2 C13 -178.63(16) . . . . ?
C18 C1 C2 C13 1.6(3) . . . . ?
C2 N2 C3 N1 0.67(18) . . . . ?
Zn1 N2 C3 N1 -162.67(13) . . . . ?
C2 N2 C3 C4 -177.83(15) . . . . ?
Zn1 N2 C3 C4 18.8(3) . . . . ?
C1 N1 C3 N2 -0.27(19) . . . . ?
O1 N1 C3 N2 -179.96(13) . . . . ?
C1 N1 C3 C4 178.35(14) . . . . ?
O1 N1 C3 C4 -1.3(2) . . . . ?
C8 N3 C4 C5 -1.5(2) . . . . ?
C8 N3 C4 C3 179.01(14) . . . . ?
N2 C3 C4 N3 178.64(15) . . . . ?
N1 C3 C4 N3 0.3(2) . . . . ?
N2 C3 C4 C5 -0.9(3) . . . . ?
N1 C3 C4 C5 -179.15(16) . . . . ?
N3 C4 C5 C6 2.0(3) . . . . ?
C3 C4 C5 C6 -178.50(15) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C5 C6 C7 C9 178.70(16) . . . . ?
C5 C6 C7 C8 -1.7(2) . . . . ?
C4 N3 C8 C12 179.48(14) . . . . ?
C4 N3 C8 C7 -0.7(2) . . . . ?
C6 C7 C8 N3 2.2(2) . . . . ?
C9 C7 C8 N3 -178.10(14) . . . . ?
C6 C7 C8 C12 -177.92(14) . . . . ?
C9 C7 C8 C12 1.7(2) . . . . ?
C6 C7 C9 C10 178.18(15) . . . . ?
C8 C7 C9 C10 -1.5(2) . . . . ?
C7 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 1.3(3) . . . . ?
C10 C11 C12 C8 -1.0(3) . . . . ?
N3 C8 C12 C11 179.34(16) . . . . ?
C7 C8 C12 C11 -0.5(2) . . . . ?
C17 N4 C13 C14 0.7(2) . . . . ?
Zn1 N4 C13 C14 178.12(12) . . . . ?
C17 N4 C13 C2 -176.70(14) . . . . ?
Zn1 N4 C13 C2 0.67(17) . . . . ?
N2 C2 C13 N4 8.3(2) . . . . ?
C1 C2 C13 N4 -172.44(16) . . . . ?
N2 C2 C13 C14 -169.01(15) . . . . ?
C1 C2 C13 C14 10.2(3) . . . . ?
N4 C13 C14 C15 -0.9(2) . . . . ?
C2 C13 C14 C15 176.23(15) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C13 N4 C17 C16 0.0(3) . . . . ?
Zn1 N4 C17 C16 -177.02(13) . . . . ?
C15 C16 C17 N4 -0.6(3) . . . . ?
