A New Bis(thioether)-Dipyrrin N2S2 Ligand and Its Coordination Behaviors to Nickel, Copper and Zinc
Wu, Tengdie; Wang, Shen; Lv, Yongxin; Fu, Tianyue; Jiang, Jinhai; Lu, Xin; Yu, Zhi-Peng; zhang, jie; Wang, Lianke; Zhou, Hong-Ping; Dalton Transactions  (2022) –; doi:10.1039/D2DT01282K

data_7710335
_publ_section_title
;
 A New Bis(thioether)-Dipyrrin N2S2 Ligand and Its Coordination Behaviors
 to Nickel, Copper and Zinc
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01282K
_journal_year                    2022
_chemical_formula_moiety         'C66 H50 F12 N4 S4 Zn'
_chemical_formula_sum            'C66 H50 F12 N4 S4 Zn'
_chemical_formula_weight         1320.71
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-09
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-04-06 deposited with the CCDC.	2022-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5949(13)
_cell_length_b                   17.6861(17)
_cell_length_c                   28.194(3)
_cell_measurement_reflns_used    6110
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.279
_cell_measurement_theta_min      2.303
_cell_volume                     6779.0(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            49426
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.359
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0798 before and 0.0641 after correction.
The Ratio of minimum to maximum transmission is 0.9113.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       plate
_exptl_crystal_F_000             2704
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     940
_refine_ls_number_reflns         11937
_refine_ls_number_restraints     368
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0534P)^2^+1.7294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                8106
_reflns_number_total             11937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01282k2.cif
_cod_data_source_block           1
_cod_original_cell_volume        6779.0(11)
_cod_database_code               7710335
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.887
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C35-C34A = C35-C34
 1.54 with sigma of 0.01
 F8A-C34A = F9A-C34A = F8-C34 = F7A-C34A = F9-C34 = F7-C34
 1.38 with sigma of 0.01
 F10-C38 = F12-C38 = F12A-C38A = F11-C38 = F10A-C38A = F11A-C38A
 1.38 with sigma of 0.01
 C38-C37 = C38A-C37
 1.54 with sigma of 0.01
 C5-C4 = C5A-C4
 1.54 with sigma of 0.01
 F3-C5 = F1A-C5A = F1-C5 = F2A-C5A = F2-C5 = F3A-C5A
 1.38 with sigma of 0.01
 F4-C1 = F5A-C1A = F5-C1 = F6A-C1A = F6-C1 = F4A-C1A
 1.38 with sigma of 0.01
 C2-C1A = C2-C1
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F3A) \\sim Ueq,
Uanis(C5A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F7) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(C34) \\sim
Ueq, Uanis(F7A) \\sim Ueq, Uanis(F8A) \\sim Ueq, Uanis(F9A) \\sim Ueq,
Uanis(C34A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F3A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(F3) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 C35, C34A, F9A, F8A, F7A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C35, C34, F9, F7, F8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C37, C38A, F12A, F11A, F10A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C37, C38, F12, F11, F10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F2A, F1A, C5A, F3A, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C4, F3, C5, F2, F1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C2, C1A, F6A, F5A, F4A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C2, C1, F6, F4, F5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(F7A)=Sof(F8A)=Sof(F9A)=Sof(C34A)=1-FVAR(1)
 Sof(F7)=Sof(F8)=Sof(F9)=Sof(C34)=FVAR(1)
 Sof(F10A)=Sof(F11A)=Sof(F12A)=Sof(C38A)=1-FVAR(2)
 Sof(F10)=Sof(F11)=Sof(F12)=Sof(C38)=FVAR(2)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C5A)=1-FVAR(3)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(C5)=FVAR(3)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(C1A)=1-FVAR(4)
 Sof(F4)=Sof(F5)=Sof(F6)=Sof(C1)=FVAR(4)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C11(H11), C12(H12), C15(H15), C18(H18), C19(H19),
 C23(H23), C24(H24), C27(H27), C30(H30), C31(H31), C36(H36), C39(H39), C41(H41),
  C44(H44), C45(H45), C48(H48), C51(H51), C52(H52), C56(H56), C57(H57),
 C60(H60), C63(H63), C64(H64)
6.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C21(H21A,H21B,H21C), C29(H29A,H29B,H29C), C33(H33A,H33B,
 H33C), C50(H50A,H50B,H50C), C54(H54A,H54B,H54C), C62(H62A,H62B,H62C), C65(H65A,
 H65B,H65C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 164 electrons were 
found in a volume of 856\%A^3^ in 2 voids per unit cell. 
This is consistent with the presence of 
1[C4H8O] per Asymmetric Unit 
which account for 160 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'