Electron-rich pyridines with <i>para</i>-N-heterocyclic imine substituents: ligand properties and coordination to CO<sub>2</sub>, SO<sub>2</sub>, BCl<sub>3</sub> and Pd<sup>II</sup> complexes.
Franzen, Jonas H.; Wilm, Lukas F. B.; Rotering, Philipp; Wurst, Klaus; Seidl, Michael; Dielmann, Fabian; Dalton transactions (Cambridge, England : 2003) 53 (2024) 11876–11883; doi:10.1039/d4dt01399a

data_7716413
_publ_section_title
;
 Electron-rich pyridines with <i>para</i>-N-heterocyclic imine
 substituents: ligand properties and coordination to CO<sub>2</sub>,
 SO<sub>2</sub>, BCl<sub>3</sub> and Pd<sup>II</sup> complexes.
;
_journal_issue                   28
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11876
_journal_page_last               11883
_journal_paper_doi               10.1039/d4dt01399a
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C16 H24 N4'
_chemical_formula_sum            'C16 H24 N4'
_chemical_formula_weight         272.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-05-08
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-08 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.74140(10)
_cell_length_b                   11.2691(2)
_cell_length_c                   13.8933(2)
_cell_measurement_reflns_used    9480
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.584
_cell_measurement_theta_min      3.129
_cell_volume                     1525.16(4)
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_collection       'Bruker Apex III'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_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  0.0191
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15931
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.591
_diffrn_reflns_theta_min         3.445
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
? was used for absorption correction.
wR2(int) was 0.1456 before and 0.0343 after correction.
The Ratio of minimum to maximum transmission is 0.9499.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1750 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         4280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+0.3251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4145
_reflns_number_total             4280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt01399a2.cif
_cod_data_source_block           compound_1
_cod_depositor_comments
'Adding full bibliography for 7716413--7716422.cif.'
_cod_database_code               7716413
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              58685
_olex2_submission_special_instructions 'No special instructions were received'