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_7710337
_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 H26 F6 N2 S2'
_chemical_formula_sum            'C33 H26 F6 N2 S2'
_chemical_formula_weight         628.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-14
_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                 93.511(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5425(14)
_cell_length_b                   22.706(3)
_cell_length_c                   28.330(4)
_cell_measurement_reflns_used    8803
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.110
_cell_measurement_theta_min      2.340
_cell_volume                     6126.8(15)
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.928
_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  0.0611
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            49056
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         1.440
_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    0.236
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1223 before and 0.0655 after correction.
The Ratio of minimum to maximum transmission is 0.8719.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       needle
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.109
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     911
_refine_ls_number_reflns         13068
_refine_ls_number_restraints     293
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0631
_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^)+(0.0794P)^2^+3.9154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1596
_refine_ls_wR_factor_ref         0.1915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7756
_reflns_number_total             13068
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01282k2.cif
_cod_data_source_block           2
_cod_database_code               7710337
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.928
_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
 F8-C50 \\sim F7A-C50 \\sim F7-C50 \\sim F9A-C50 \\sim F9-C50 \\sim F8A-C50
 with sigma of 0.02
 F12A-C53 \\sim F10-C53 \\sim F10A-C53 \\sim F11-C53 \\sim F11A-C53 \\sim
F12-C53
 with sigma of 0.02
 F1A-C21 \\sim F2-C21 \\sim F2A-C21 \\sim F3-C21 \\sim F3A-C21 \\sim F1-C21
 with sigma of 0.02
 F5-C17 \\sim F5A-C17 \\sim F6-C17 \\sim F6A-C17 \\sim F4-C17 \\sim F4A-C17
 with sigma of 0.02
 S4-C66 \\sim S4A-C66A
 with sigma of 0.02
 S4-C65 \\sim S4A-C65
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F8A, C50, F7A, F9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F8, C50, F9, F7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F12A, F10A, F11A, C53
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C53, F12, F10, F11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C21, F2A, F1A, F3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C21, F2, F3, F1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F4A, C17, F6A, F5A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F4, F5, F6, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C25, C26, C27, C28, C29, C30, C31, C32, S2, C33
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S4A, C65, C66A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C65, S4, C66
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F8A)=Sof(F9A)=Sof(F7A)=1-FVAR(1)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(1)
 Sof(F12A)=Sof(F11A)=Sof(F10A)=1-FVAR(2)
 Sof(F10)=Sof(F11)=Sof(F12)=FVAR(2)
 Sof(F2A)=Sof(F3A)=Sof(F1A)=1-FVAR(3)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(3)
 Sof(F4A)=Sof(F6A)=Sof(F5A)=1-FVAR(4)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(4)
 Sof(S4A)=Sof(C66A)=Sof(H66D)=Sof(H66E)=Sof(H66F)=1-FVAR(5)
 Sof(S4)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=FVAR(5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C8(H8), C10(H10), C11(H11), C15(H15), C18(H18), C19(H19),
 C23(H23), C24(H24), C27(H27), C30(H30), C31(H31), C37(H37), C39(H39), C40(H40),
  C43(H43), C44(H44), C48(H48), C51(H51), C54(H54), C56(H56), C57(H57),
 C60(H60), C63(H63), C64(H64)
5.b Fitted hexagon refined as free rotating group:
 C26(C27,C28,C30,C31,C32)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C29(H29A,H29B,H29C), C33(H33A,H33B,H33C),
 C34(H34A,H34B,H34C), C41(H41A,H41B,H41C), C62(H62A,H62B,H62C), C66(H66A,H66B,
 H66C), C66A(H66D,H66E,H66F)
;
_olex2_submission_special_instructions 'No special instructions were received'