Benzimidazole-triazole ligands with pendent triazole functionality: unexpected formation and effects on copper-catalyzed aerobic alcohol oxidation.
Kongkaew, Manisa; Sitthisuwannakul, Kannika; Nakarajouyphon, Vasut; Pornsuwan, Soraya; Kongsaeree, Palangpon; Sangtrirutnugul, Preeyanuch; Dalton transactions (Cambridge, England : 2003) 45 (2016) 16810–16819; doi:10.1039/c6dt02770a

data_7040583
_publ_section_title
;
 Benzimidazole-triazole ligands with pendent triazole functionality:
 unexpected formation and effects on copper-catalyzed aerobic alcohol
 oxidation.
;
_journal_issue                   42
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16810
_journal_page_last               16819
_journal_paper_doi               10.1039/c6dt02770a
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C20 H30 Cl2 Cu N8 Si2, C2 H3 N'
_chemical_formula_sum            'C22 H33 Cl2 Cu N9 Si2'
_chemical_formula_weight         614.19
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-08-01
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2016.05.11 svn.r3296 for OlexSys, GUI svn.r3563)
;
_audit_update_record
;
2016-08-12 deposited with the CCDC.
2016-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                100.7014(10)
_cell_angle_beta                 103.0788(11)
_cell_angle_gamma                105.8527(9)
_cell_formula_units_Z            2
_cell_length_a                   8.9699(2)
_cell_length_b                   13.5062(4)
_cell_length_c                   14.1297(4)
_cell_measurement_reflns_used    8280
_cell_measurement_temperature    293
_cell_measurement_theta_max      3.55
_cell_measurement_theta_min      27.45
_cell_volume                     1547.01(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.916
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  KappaCCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5489
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        22.505
_diffrn_reflns_theta_max         22.505
_diffrn_reflns_theta_min         2.469
_exptl_absorpt_coefficient_mu    0.983
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_correction_T_min  0.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             638
_exptl_crystal_recrystallization_method 'slow evaporation from CH3CN solution'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.749
_refine_diff_density_min         -1.119
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.021(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0768
_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^)+(0.1751P)^2^+1.3761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2229
_refine_ls_wR_factor_ref         0.2308
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3293
_reflns_number_total             3713
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt02770a2.cif
_cod_data_source_block           shelxl1
_cod_depositor_comments
'Adding full bibliography for 7040582--7040583.cif.'
_cod_original_cell_volume        1547.02(7)
_cod_database_code               7040583
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13A-C12A \\sim C13A-C11A \\sim C12A-C11A
 with sigma of 0.04
 Si1A-C10 \\sim Si1A-C13A \\sim Si1A-C12A \\sim Si1A-C11A
 with sigma of 0.02
 C13-C12 \\sim C13-C11 \\sim C12-C11
 with sigma of 0.04
 Si1-C10 \\sim Si1-C13 \\sim Si1-C12 \\sim Si1-C11
 with sigma of 0.02
 C20-C18 \\sim C20-C19 \\sim C18-C19
 with sigma of 0.04
 Si2-C17 \\sim Si2-C20 \\sim Si2-C18 \\sim Si2-C19
 with sigma of 0.02
 C20A-C18A \\sim C20A-C19A \\sim C18A-C19A
 with sigma of 0.04
 Si2A-C17 \\sim Si2A-C20A \\sim Si2A-C18A \\sim Si2A-C19A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Si1) = Uanis(Si1A)
Uanis(Si2) = Uanis(Si2A)
4. Rigid body (RIGU) restrains
 Si2, C20, C18, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Si1, C13, C12, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Si2A, C20A, C18A, C19A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Si1A, C13A, C12A, C11A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H17C)=Sof(H17D)=Sof(Si2A)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=
 Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=1-FVAR(1)
 Sof(Si2)=Sof(H17A)=Sof(H17B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C18)=
 Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(1)
 Fixed Sof: H10A(0.5) H10B(0.5) H10C(0.5) H10D(0.5) Si1(0.5) C13(0.5)
 H13A(0.5) H13B(0.5) H13C(0.5) C12(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C11(0.5)
 H11A(0.5) H11C(0.5) H11B(0.5) Si1A(0.5) C13A(0.5) H13D(0.5) H13E(0.5)
 H13F(0.5) C12A(0.5) H12D(0.5) H12E(0.5) H12F(0.5) C11A(0.5) H11D(0.5)
 H11E(0.5) H11F(0.5)
6.a Riding coordinates:
 C11(H11A,H11C,H11B), C20A(H20D,H20E,H20F)
6.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B), C17(H17C,H17D), C10(H10A,H10B), C10(H10C,H10D)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C16(H16), C9(H9), C6(H6), C5(H5), C4(H4)
6.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C13A(H13D,H13E,H13F),
 C12A(H12D,H12E,H12F), C11A(H11D,H11E,H11F), C18A(H18D,H18E,H18F), C19A(H19D,
 H19E,H19F)
;
_shelx_res_checksum              84676
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'