2,6-Bis(benzimidazol-2-yl)pyridines as more electron-rich and sterically accessible alternatives to 2,6-bis(imino)pyridine for group 13 coordination chemistry.
Swidan, Ala'aeddeen; Binder, Justin F.; Onge, Blake J St; Suter, Riccardo; Burford, Neil; Macdonald, Charles L. B.; Dalton transactions (Cambridge, England : 2003) 48 (2019) 1284–1291; doi:10.1039/c8dt04276d

data_7048406
_publ_section_title
;
 2,6-Bis(benzimidazol-2-yl)pyridines as more electron-rich and sterically
 accessible alternatives to 2,6-bis(imino)pyridine for group 13
 coordination chemistry.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1284
_journal_page_last               1291
_journal_paper_doi               10.1039/c8dt04276d
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C37 H21 Cl2 F12 Ga N5, Cl4 Ga'
_chemical_formula_sum            'C37 H21 Cl6 F12 Ga2 N5'
_chemical_formula_weight         1115.73
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-27 deposited with the CCDC.
2018-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                81.875(2)
_cell_angle_beta                 86.671(3)
_cell_angle_gamma                75.708(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0074(7)
_cell_length_b                   14.0425(10)
_cell_length_c                   17.2131(14)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      32.63
_cell_measurement_theta_min      3.07
_cell_volume                     2088.1(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       APEX3
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX3 Photon 100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            121980
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.034
_diffrn_reflns_theta_min         2.840
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.765
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0707 before and 0.0567 after correction. The Ratio of minimum to maximum transmission is 0.8769. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_description       prism
_exptl_crystal_F_000             1100
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.692
_refine_diff_density_min         -0.984
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     587
_refine_ls_number_reflns         12167
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0326P)^2^+7.0942P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10075
_reflns_number_total             12167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt04276d2.cif
_cod_data_source_block           as721_p-1_new
_cod_depositor_comments
'Adding full bibliography for 7048404--7048410.cif.'
_cod_database_code               7048406
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.620
_shelx_estimated_absorpt_t_min   0.585
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F19-F20
 1.32 with sigma of 0.02
 C01K-F0AA \\sim C01K-F0AB
 with sigma of 0.02
 C01K-F2 \\sim C01K-F2A
 with sigma of 0.02
 C01K-F3 \\sim C01K-F3A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F20, F18, F19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2, F3A, F3, F0AB, C01K, F0AA, F2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F2A)=Sof(F3A)=Sof(F0AB)=1-FVAR(1)
 Sof(F0AA)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C012(H01A,H01B)
5.b Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00P(H00P), C00R(H00R), C00U(H00U), C00W(H00W), C00X(H00X),
 C010(H010), C011(H011), C013(H013), C015(H015), C016(H016), C019(H019),
 C01A(H01C), C01C(H01D), C01D(H01E), C01I(H01I), C01J(H01J)
;
_shelx_res_checksum              25510
_olex2_submission_special_instructions 'No special instructions were received'