Luminescence of ESIPT-capable zinc(II) complexes with a 1-hydroxy-1H-imidazole-based ligand: exploring the impact of substitution in the proton-donating moiety
Shekhovtsov, Nikita; Nikolaenkova, Elena B.; Vorob'eva, Sofia; Plyusnin, Victor F.; Vinogradova, Katerina A.; Sukhikh, Taisiya; Tikhonov, Alexsei Ya.; Bushuev, Mark B.; Dalton Transactions  (2023) –; doi:10.1039/D3DT01190A

data_7713052
_publ_section_title
;
 Luminescence of ESIPT-capable zinc(II) complexes with a
 1-hydroxy-1H-imidazole-based ligand: exploring the impact of substitution
 in the proton-donating moiety
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01190A
_journal_year                    2023
_chemical_formula_moiety         '(C19 H15 Cl2 N5 O Zn), 0.75(C H2 Cl2)'
_chemical_formula_sum            'C19.75 H16.5 Cl3.5 N5 O Zn'
_chemical_formula_weight         529.28
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-04-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-20 deposited with the CCDC.	2023-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                106.5120(10)
_cell_angle_beta                 100.9700(10)
_cell_angle_gamma                107.4580(10)
_cell_formula_units_Z            4
_cell_length_a                   10.6299(2)
_cell_length_b                   13.3659(3)
_cell_length_c                   17.2735(4)
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.30
_cell_measurement_theta_min      2.51
_cell_volume                     2140.29(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            42861
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.621
_diffrn_reflns_theta_min         1.730
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.607
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_description       prism
_exptl_crystal_F_000             1070
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     611
_refine_ls_number_reflns         11719
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0386
_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/[\s^2^(Fo^2^)+(0.0336P)^2^+2.2540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9959
_reflns_number_total             11719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01190a2.cif
_cod_data_source_block           gr-88-72
_cod_original_formula_sum        'C19.75 H16.5 Cl3.50 N5 O Zn'
_cod_database_code               7713052
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.772
_olex2_refinement_description
;
1. Restrained distances
 Cl11-C1A = Cl12-C1A
 1.771 with sigma of 0.01
 Cl11-Cl12
 2.916 with sigma of 0.03
 Cl13-C1B = Cl14-C1B
 1.771 with sigma of 0.01
 Cl13-Cl14
 2.916 with sigma of 0.03
 O2-H2A = O1-H1
 0.84 with sigma of 0.02
 Zn4-Cl8 \\sim Zn2-Cl4 \\sim Zn2-Cl3 \\sim Zn4-Cl7
 with sigma of 0.02
 Zn3-Cl6 \\sim Zn1-Cl2 \\sim Zn3-Cl5 \\sim Zn1-Cl1
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Cl11 \\sim Cl12 \\sim C1A: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
Cl13 \\sim Cl14 \\sim C1B: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
Uiso(Cl12) = Uiso(Cl11) = Uiso(C1A)
Uiso(N16) = Uiso(N17) = Uiso(N15) = Uiso(C67) = Uiso(C63) = Uiso(C68) =
Uiso(C71) = Uiso(C58) = Uiso(C62) = Uiso(C66) = Uiso(C64) = Uiso(C69) =
Uiso(N18) = Uiso(C72) = Uiso(C59) = Uiso(C61) = Uiso(C65) = Uiso(C70) =
Uiso(O4) = Uiso(N19) = Uiso(C73) = Uiso(C60) = Uiso(C76) = Uiso(C74) = Uiso(C75)
Uiso(Cl13) = Uiso(C1B) = Uiso(Cl14)
Uiso(N11) = Uiso(N10) = Uiso(N12) = Uiso(C44) = Uiso(C48) = Uiso(C43) =
Uiso(C39) = Uiso(C49) = Uiso(C52) = Uiso(C45) = Uiso(C47) = Uiso(C42) =
Uiso(C40) = Uiso(C50) = Uiso(N13) = Uiso(C53) = Uiso(C46) = Uiso(C41) =
Uiso(C51) = Uiso(O3) = Uiso(N14) = Uiso(C54) = Uiso(C57) = Uiso(C55) = Uiso(C56)
Uiso(Cl12) = Uiso(Cl11) = Uiso(C1A) = Uiso(C1B) = Uiso(Cl13) = Uiso(Cl14)
Uiso(Cl7) = Uiso(Cl8)
3. Rigid body (RIGU) restrains
 Cl11, Cl12, C1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl13, Cl14, C1B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Zn4)=Sof(Cl7)=Sof(Cl8)=Sof(N16)=Sof(O4)=Sof(N15)=Sof(N17)=Sof(N18)=
 Sof(N19)=Sof(C58)=Sof(H58)=Sof(C59)=Sof(H59)=Sof(C60)=Sof(H60)=Sof(C61)=
 Sof(H61)=Sof(C62)=Sof(C63)=Sof(C64)=Sof(H64)=Sof(C65)=Sof(H65)=Sof(C66)=
 Sof(H66)=Sof(C67)=Sof(C68)=Sof(C69)=Sof(C70)=Sof(H70A)=Sof(H70B)=Sof(H70C)=
 Sof(C71)=Sof(C72)=Sof(C73)=Sof(H73)=Sof(C74)=Sof(H74)=Sof(C75)=Sof(H75)=
 Sof(C76)=Sof(H76)=1-FVAR(1)
 Sof(Zn2)=Sof(Cl3)=Sof(Cl4)=Sof(O2)=Sof(H2A)=Sof(N5)=Sof(N6)=Sof(N7)=Sof(N8)=
 Sof(N9)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C23)=
 Sof(H23)=Sof(C24)=Sof(C25)=Sof(C26)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=
 Sof(C28)=Sof(C29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32)=
 Sof(C33)=Sof(C34)=Sof(C35)=Sof(H35)=Sof(C36)=Sof(H36)=Sof(C37)=Sof(H37)=
 Sof(C38)=Sof(H38)=FVAR(1)
 Sof(Zn3)=Sof(Cl5)=Sof(Cl6)=Sof(N11)=Sof(O3)=Sof(N10)=Sof(N12)=Sof(N13)=
 Sof(N14)=Sof(C39)=Sof(H39)=Sof(C40)=Sof(H40)=Sof(C41)=Sof(H41)=Sof(C42)=
 Sof(H42)=Sof(C43)=Sof(C44)=Sof(C45)=Sof(H45)=Sof(C46)=Sof(H46)=Sof(C47)=
 Sof(H47)=Sof(C48)=Sof(C49)=Sof(C50)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=
 Sof(C52)=Sof(C53)=Sof(C54)=Sof(H54)=Sof(C55)=Sof(H55)=Sof(C56)=Sof(H56)=
 Sof(C57)=Sof(H57)=1-FVAR(2)
 Sof(Zn1)=Sof(Cl1)=Sof(Cl2)=Sof(O1)=Sof(H1)=Sof(N1)=Sof(N2)=Sof(N3)=Sof(N4)=
 Sof(N20)=Sof(C1)=Sof(H1A)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=
 Sof(C5)=Sof(C6)=Sof(C7)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(C10)=
 Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(C15)=
 Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=FVAR(2)
 Sof(Cl13)=Sof(Cl14)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=0.5*(1-FVAR(4))
 Sof(Cl11)=Sof(Cl12)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=0.5*FVAR(4)
5.a Free rotating group:
 N11(O3,N10,N12,N13,N14,C39,C40,C41,C42,C43,C44,C45,C46,C47,C48,C49,C50,C51,
 C52,C53,C54,C55,C56,C57), N16(O4,N15,N17,N18,N19,C58,C59,C60,C61,C62,C63,C64,
 C65,C66,C67,C68,C69,C70,C71,C72,C73,C74,C75,C76)
5.b Secondary CH2 refined with riding coordinates:
 C77(H77A,H77B), C1A(H1AA,H1AB), C1B(H1BA,H1BB)
5.c Aromatic/amide H refined with riding coordinates:
 C39(H39), C40(H40), C41(H41), C42(H42), C45(H45), C46(H46), C47(H47),
 C54(H54), C55(H55), C56(H56), C57(H57), C1(H1A), C2(H2), C3(H3), C4(H4),
 C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
  C21(H21), C22(H22), C23(H23), C30(H30), C31(H31), C32(H32), C35(H35),
 C36(H36), C37(H37), C38(H38), C58(H58), C59(H59), C60(H60), C61(H61), C64(H64),
  C65(H65), C66(H66), C73(H73), C74(H74), C75(H75), C76(H76)
5.d Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C8(H8A,H8B,H8C), C27(H27A,H27B,H27C), C70(H70A,H70B,H70C)
;
_shelx_res_checksum              76254
_shelx_hkl_checksum              25078
_olex2_submission_special_instructions 'No special instructions were received'