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_7710338
_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         'C33 H25 Cl Cu F6 N2 S2'
_chemical_formula_sum            'C33 H25 Cl Cu F6 N2 S2'
_chemical_formula_weight         726.66
_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     dual
_audit_creation_date             2022-03-21
_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                69.500(2)
_cell_angle_beta                 69.628(2)
_cell_angle_gamma                62.269(2)
_cell_formula_units_Z            4
_cell_length_a                   16.2289(19)
_cell_length_b                   16.6073(19)
_cell_length_c                   17.416(2)
_cell_measurement_reflns_used    6741
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.666
_cell_measurement_theta_min      2.400
_cell_volume                     3793.4(8)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27615
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.454
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1102 before and 0.0432 after correction.
The Ratio of minimum to maximum transmission is 0.8553.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       plate
_exptl_crystal_F_000             1476
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.453
_refine_diff_density_min         -1.122
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     967
_refine_ls_number_reflns         13245
_refine_ls_number_restraints     726
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0766
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1235P)^2^+6.5838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2147
_refine_ls_wR_factor_ref         0.2412
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8681
_reflns_number_total             13245
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01282k2.cif
_cod_data_source_block           1_CCDC2
_cod_database_code               7710338
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.788
_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
 S2-C66 = S2-C32
 1.82 with sigma of 0.02
 F6A-C16A = C16A-F5A
 1.38 with sigma of 0.02
 F5A-C16A = C16A-F4A
 1.38 with sigma of 0.02
 F6A-C16A = C16A-F4A
 1.38 with sigma of 0.02
 F2-C19 = C19-F3
 1.38 with sigma of 0.02
 F3A-C19A = C19A-F2A
 1.38 with sigma of 0.02
 F1-C19 = C19-F3
 1.38 with sigma of 0.02
 F2-C19 = C19-F1
 1.38 with sigma of 0.02
 F2A-C19A = C19A-F1A
 1.38 with sigma of 0.02
 F1A-C19A = C19A-F3A
 1.38 with sigma of 0.02
 F10-C49 = C49-F11
 1.38 with sigma of 0.02
 F10A-C49A = C49A-F11A
 1.38 with sigma of 0.02
 F12-C49 = C49-F11
 1.38 with sigma of 0.02
 F12-C49 = C49-F10
 1.38 with sigma of 0.02
 F10A-C49A = C49A-F12A
 1.38 with sigma of 0.02
 F11A-C49A = C49A-F12A
 1.38 with sigma of 0.02
 F8A-C52 = C52-F7A
 1.38 with sigma of 0.02
 F7-C52 = C52-F8
 1.38 with sigma of 0.02
 F9A-C52 = C52-F8A
 1.38 with sigma of 0.02
 F9-C52 = C52-F8
 1.38 with sigma of 0.02
 F7-C52 = C52-F9
 1.38 with sigma of 0.02
 F7A-C52 = C52-F9A
 1.38 with sigma of 0.02
 F6A-F5A
 2.254 with sigma of 0.04
 F5A-F4A
 2.254 with sigma of 0.04
 F6A-F4A
 2.254 with sigma of 0.04
 F3A-F2A
 2.254 with sigma of 0.04
 F1A-F3A
 2.254 with sigma of 0.04
 F2-F1
 2.254 with sigma of 0.04
 F1-F3
 2.254 with sigma of 0.04
 F2-F3
 2.254 with sigma of 0.04
 F2A-F1A
 2.254 with sigma of 0.04
 F12-F11
 2.254 with sigma of 0.04
 F10-F11
 2.254 with sigma of 0.04
 F10A-F12A
 2.254 with sigma of 0.04
 F12-F10
 2.254 with sigma of 0.04
 F10A-F11A
 2.254 with sigma of 0.04
 F11A-F12A
 2.254 with sigma of 0.04
 F9A-F8A
 2.254 with sigma of 0.04
 F9-F8
 2.254 with sigma of 0.04
 F7-F8
 2.254 with sigma of 0.04
 F7-F9
 2.254 with sigma of 0.04
 F7A-F9A
 2.254 with sigma of 0.04
 F8A-F7A
 2.254 with sigma of 0.04
 S2-C66 \\sim S2-C32
 with sigma of 0.02
 F4-C16 \\sim F6A-C16A \\sim F6-C16 \\sim F5A-C16A \\sim F5-C16 \\sim F4A-C16A
 with sigma of 0.02
 C16-C15 \\sim C16A-C15
 with sigma of 0.02
 C19-C18 \\sim C19A-C18
 with sigma of 0.02
 C49A-C48 \\sim C49-C48
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F4 \\sim F5 \\sim F6 \\sim C16 \\sim C16A \\sim F4A \\sim F5A \\sim F6A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C19 \\sim F1 \\sim F3 \\sim F2 \\sim C19A \\sim F3A \\sim F1A \\sim F2A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F12 \\sim F11 \\sim F10 \\sim C49 \\sim C49A \\sim F11A \\sim F10A \\sim F12A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F7 \\sim F8 \\sim F9 \\sim C52 \\sim F8A \\sim F7A \\sim F9A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C66) \\sim Ueq, Uanis(C32) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 C48
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C16, F6, F4, F5, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 F6A, C16A, F4A, F5A, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C18
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C19, F1, C18, F2, F3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C18, F2A, C19A, F3A, F1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C48, C49A, F10A, F12A, F11A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C48, C49, F10, F11, F12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 F8A, F7A, F9A, C52
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 F8, F7, F9, C52
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(C16A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=1-
 FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=Sof(C16)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=FVAR(1)
 Sof(C19A)=Sof(F3A)=Sof(F1A)=Sof(F2A)=1-FVAR(2)
 Sof(C19)=Sof(F1)=Sof(F3)=Sof(F2)=FVAR(2)
 Sof(C49A)=Sof(F11A)=Sof(F10A)=Sof(F12A)=1-FVAR(3)
 Sof(F12)=Sof(F11)=Sof(F10)=Sof(C49)=FVAR(3)
 Sof(F8A)=Sof(F7A)=Sof(F9A)=1-FVAR(4)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(4)
6.a Riding coordinates:
 C66(H66A,H66B,H66C)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C9(H9), C10(H10), C14(H14), C17(H17), C20(H20),
 C22(H22), C23(H23), C26(H26), C29(H29), C30(H30), C35(H35), C36(H36), C39(H39),
  C42(H42), C43(H43), C47(H47), C50(H50), C53(H53), C55(H55), C56(H56),
 C59(H59), C62(H62), C63(H63)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C02H(H02A,H02B,H02C), C28(H28A,H28B,H28C), C33(H33A,H33B,
 H33C), C38(H38A,H38B,H38C), C61(H61A,H61B,H61C), C65(H65A,H65B,H65C), C32(H32A,
 H32B,H32C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 211 electrons were 
found in a volume of 708\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1[CHCl3] per Asymmetric Unit 
which account for 232 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'