Diverse Coordination Modes of Bidentate COC and Tridentate CNC Ligands Comprising 1,2,3-Triazol-5-ylidenes
Tolley, Lewis C.; Strydom, Ian; Louw, Wynand J.; Fernandes, Manuel A.; Bezuidenhout, Daniela I.; Guisado-Barrios, Gregorio; ACS Omega 4 (2019) 6360–; doi:10.1021/acsomega.9b00514

data_4515032
_publ_section_title
;
 Diverse Coordination Modes of Bidentate COC and Tridentate CNC Ligands
 Comprising 1,2,3-Triazol-5-ylidenes
;
_journal_issue                   4
_journal_name_full               'ACS Omega'
_journal_page_first              6360
_journal_paper_doi               10.1021/acsomega.9b00514
_journal_volume                  4
_journal_year                    2019
_chemical_formula_moiety
;
C54 H74 N6 O, 2(F6 P), [+ disordered DCM solvent]
;
_chemical_formula_sum            'C54 H74 F12 N6 O P2'
_chemical_formula_weight         1113.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-23 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 99.325(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.3474(7)
_cell_length_b                   19.7123(10)
_cell_length_c                   13.7256(6)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      3.19
_cell_volume                     3296.6(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Apex II'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            90921
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.918
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9420
_exptl_absorpt_correction_T_min  0.8785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) 
was 0.0797 before and 0.0574 after correction. The Ratio of minimum to 
maximum transmission is 0.9326. The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_description       plate
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         5793
_refine_ls_number_restraints     168
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0829
_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^)+(0.0863P)^2^+5.3082P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2153
_refine_ls_wR_factor_ref         0.2246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4853
_reflns_number_total             5793
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao9b00514_si_002.cif
_cod_data_source_block
Ligand_[H2(COC)](PF6)2_mo_17mv_db3_lctsc005_0f_sq
_cod_database_code               4515032
_publcif_datablock.id            {5c956bd2-6c35-47ed-92e2-d0699e382e37}
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.945
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C26-C27 \\sim C26-C27A \\sim C26-C28 \\sim C26-C28A
 with sigma of 0.02
 C27-C28 \\sim C27A-C28A
 with sigma of 0.02
 C22-C26 \\sim C22-C26A
 with sigma of 0.02
 C26-C27 \\sim C26A-C27
 with sigma of 0.02
 C26-C28 \\sim C26A-C28
 with sigma of 0.02
 C26-C27A \\sim C26A-C27A
 with sigma of 0.02
 C26-C28A \\sim C26A-C28A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F4) = Uanis(F4A)
4. Rigid body (RIGU) restrains
 C26A, C27A, C28A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C26, C27, C28
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F1, F2, F3, F4, F5, F6, P1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1A, F2A, F3A, F4A, F5A, F6A, P1A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Same fragment restrains
{F1, F2, F3, F4, F5, F6, P1} sigma for 1-2: 0.005, 1-3: 0.04
as
{F1A, F2A, F3A, F4A, F5A, F6A, P1A}
6. Others
 Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=Sof(C28A)=
 Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=Sof(C28)=Sof(H28A)=
 Sof(H28B)=Sof(H28C)=FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(P1A)=1-FVAR(2)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=Sof(P1)=FVAR(2)
 Fixed Sof: H1(0.5) H2(0.5) C3(0.5) H3A(0.5) H3B(0.5) C4(0.5) H4A(0.5)
 H4B(0.5) O1(0.5)
7.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C23(H23), C26(H26), C26A(H26A)
7.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
7.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C8(H8), C9(H9), C19(H19), C20(H20), C21(H21)
7.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C), C27A(H27D,H27E,H27F), C28A(H28D,H28E,H28F)
;
_shelx_res_checksum              34733
_shelx_hkl_checksum              80670
_shelx_fab_checksum              72636
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'