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_7048404
_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 H25 Cl Fe Ga N5 O4, 2(C4 H8 O)'
_chemical_formula_sum            'C45 H41 Cl Fe Ga N5 O6'
_chemical_formula_weight         908.85
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-27
_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                90
_cell_angle_beta                 92.701(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7841(14)
_cell_length_b                   15.069(2)
_cell_length_c                   28.034(4)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.311
_cell_measurement_theta_min      2.928
_cell_volume                     4128.6(10)
_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      170.05
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_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  0.0777
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            64624
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.733
_diffrn_reflns_theta_min         2.928
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1000 before and 0.0820 after correction. The Ratio of minimum to maximum transmission is 0.7815. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       prism
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         8735
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0623
_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^)+(0.0510P)^2^+11.6170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1569
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6749
_reflns_number_total             8735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt04276d2.cif
_cod_data_source_block           as1130_p21c
_cod_depositor_comments
'Adding full bibliography for 7048404--7048410.cif.'
_cod_original_cell_volume        4128.8(10)
_cod_database_code               7048404
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.759
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C5-C6 \\sim C6-C1A \\sim C1A-C1B
 with sigma of 0.02
 O5-C5 \\sim O5-C1B
 with sigma of 0.02
 O5-C6 \\sim O5-C1A
 with sigma of 0.04
 C6-C1B \\sim C5-C1A
 with sigma of 0.04
 C1C-C1D \\sim C1D-C1E \\sim C1E-C1F
 with sigma of 0.02
 O6-C1C \\sim O6-C1F
 with sigma of 0.02
 O6-C1D \\sim O6-C1E
 with sigma of 0.04
 C1D-C1F \\sim C1C-C1E
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O5 \\sim C5 \\sim C6 \\sim C1A \\sim C1B: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
O6 \\sim C1C \\sim C1D \\sim C1E \\sim C1F: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 O5, C5, C6, C1A, C1B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O6, C1C, C1D, C1E, C1F
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C27(H27A,H27B), C5(H5A,H5B), C6(H6A,H6B), C1A(H1AA,H1AB),
 C1B(H1BA,H1BB), C1C(H1CA,H1CB), C1D(H1DA,H1DB), C1E(H1EA,H1EB), C1F(H1FA,H1FB)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C9(H9), C2(H2), C22(H22), C0AA(H0AA), C26(H26), C3(H3),
 C18(H18), C24(H24), C29(H29), C30(H30), C4(H4), C25(H25), C15(H15), C31(H31),
 C23(H23), C17(H17), C33(H33), C16(H16), C32(H32)
;
_shelx_res_checksum              66664
_olex2_submission_special_instructions 'No special instructions were received'