Optimised synthesis of monoanionic bis(NHC)-pincer ligand precursors and their Li-complexes
Jürgens, Eva; Buys, Kai N.; Schmidt, Anna-Theresa; Furfari, Samantha K.; Cole, Marcus L.; Moser, Michael; Rominger, Frank; Kunz, Doris; New J. Chem. 40 (2016) 9160–; doi:10.1039/C6NJ01941B

data_7055771
_publ_section_title
;
 Optimised synthesis of monoanionic bis(NHC)-pincer ligand precursors and
 their Li-complexes
;
_journal_issue                   11
_journal_name_full               'New J. Chem.'
_journal_page_first              9160
_journal_paper_doi               10.1039/C6NJ01941B
_journal_volume                  40
_journal_year                    2016
_chemical_formula_moiety         'C32 H43 N5, 2(I)'
_chemical_formula_sum            'C32 H43 I2 N5'
_chemical_formula_weight         751.51
_chemical_properties_physical    ', Hygroscopic'
_chemical_temperature_decomposition 535
_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_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.23 svn.r3337 for OlexSys, GUI svn.r5217)
;
_audit_update_record
;
2016-08-26 deposited with the CCDC.
2016-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                69.64(2)
_cell_angle_beta                 80.26(2)
_cell_angle_gamma                76.44(2)
_cell_formula_units_Z            4
_cell_length_a                   11.373(6)
_cell_length_b                   18.404(10)
_cell_length_c                   23.130(12)
_cell_measurement_reflns_used    8906
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.506
_cell_measurement_theta_min      1.751
_cell_volume                     4392(4)
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_reduction        'SAINT V8.32B (?, 2016)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.1113
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            71205
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_min         1.751
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.453
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1808 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.7817.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       prism
_exptl_crystal_F_000             1504
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane, hexane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.920
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     785
_refine_ls_number_reflns         22907
_refine_ls_number_restraints     303
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.1517
_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1490P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2023
_refine_ls_wR_factor_ref         0.2583
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11097
_reflns_number_total             22907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6nj01941b2.cif
_cod_data_source_block           new
_cod_depositor_comments
;
  Moved the _audit_creation_method data item out of the loop.

  Antanas Vaitkus,
  2019-03-01

The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been '535
dec.'. The value '535 dec.' was changed to '535'.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7055764--7055771.cif.
;
_cod_database_code               7055771
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C26B-C27B \\sim C26B-C28B \\sim C27B-C28B \\sim C26C-C27C \\sim C26C-C28C
\\sim C27C-C28C
 with sigma of 0.04
 C30B-C31B \\sim C30B-C32B \\sim C31B-C32B \\sim C30C-C31C
 with sigma of 0.04
 C25B-C26B \\sim C25B-C27B \\sim C25B-C28B \\sim C25B-C26C \\sim C25B-C27C
\\sim C25B-C28C
 with sigma of 0.02
 C29B-C30B \\sim C29B-C31B \\sim C29B-C32B \\sim C29B-C30C \\sim C29B-C31C
\\sim C29B-C32C
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C25B \\sim C26B \\sim C27B \\sim C28B \\sim C26C \\sim C27C \\sim C28C: within
1.7A with sigma of 0.03 and sigma for terminal atoms of 0.06
C26B \\sim C27B \\sim C28B \\sim C26C \\sim C27C \\sim C28C: within 3A with
sigma of 0.03 and sigma for terminal atoms of 0.06
C29B \\sim C30B \\sim C31B \\sim C32B \\sim C30C \\sim C31C \\sim C32C: within
1.7A with sigma of 0.03 and sigma for terminal atoms of 0.06
C30B \\sim C31B \\sim C32B \\sim C30C \\sim C31C \\sim C32C: within 3A with
sigma of 0.03 and sigma for terminal atoms of 0.06
4. Others
 Sof(C28C)=Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(C27C)=Sof(H27D)=Sof(H27E)=
 Sof(H27F)=Sof(C26C)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(C26B)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C27B)=Sof(H27A)=Sof(H27B)=
 Sof(H27C)=Sof(C28B)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(1)
 Sof(C31C)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C30C)=Sof(H30D)=Sof(H30E)=
 Sof(H30F)=Sof(C32C)=Sof(H32D)=Sof(H32E)=Sof(H32F)=1-FVAR(2)
 Sof(C30B)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C31B)=Sof(H31A)=Sof(H31B)=
 Sof(H31C)=Sof(C32B)=Sof(H32B)=Sof(H32A)=Sof(H32C)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C4B(H4B), C10B(H10B), C4A(H4A), C10A(H10A)
5.b Aromatic/amide H refined with riding coordinates:
 N1B(H1B), C1B(H1BA), C2B(H2B), C3B(H3B), C7B(H7B), C8B(H8B), C9B(H9B),
 C15B(H15B), C17B(H17B), C20B(H20B), C22B(H22B), N1A(H1A), C1A(H1AA), C2A(H2A),
 C3A(H3A), C7A(H7A), C8A(H8A), C9A(H9A), C15A(H15A), C17A(H17A), C20A(H20A),
 C22A(H22A)
5.c Idealised Me refined as rotating group:
 C5B(H5BA,H5BB,H5BC), C6B(H6BA,H6BB,H6BC), C11B(H11A,H11B,H11C), C12B(H12A,
 H12B,H12C), C26B(H26A,H26B,H26C), C27B(H27A,H27B,H27C), C28B(H28A,H28B,H28C),
 C30B(H30A,H30B,H30C), C31B(H31A,H31B,H31C), C32B(H32B,H32A,H32C), C5A(H5AA,
 H5AB,H5AC), C6A(H6AA,H6AB,H6AC), C11A(H11D,H11E,H11F), C12A(H12D,H12E,H12F),
 C26A(H26G,H26H,H26I), C27A(H27G,H27H,H27I), C28A(H28G,H28H,H28I), C30A(H30G,
 H30H,H30I), C31A(H31G,H31H,H31I), C32A(H32G,H32H,H32I), C28C(H28D,H28E,H28F),
 C27C(H27D,H27E,H27F), C26C(H26D,H26E,H26F), C31C(H31D,H31E,H31F), C30C(H30D,
 H30E,H30F), C32C(H32D,H32E,H32F)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'MiTeGen liquid wick'
_olex2_submission_special_instructions 'No special instructions were received'