Carbene-derived α-acyl formamidinium cations: organic molecules with readily tunable multiple redox processes.
Deardorff, Cassie L.; Eric Sikma, R.; Rhodes, Christopher P.; Hudnall, Todd W.; Chemical communications (Cambridge, England) 52 (2016) 9024–9027; doi:10.1039/c5cc06322a

data_7124582
_publ_section_title
;
 Carbene-derived \a-acyl formamidinium cations: organic molecules with
 readily tunable multiple redox processes.
;
_journal_issue                   58
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9024
_journal_page_last               9027
_journal_paper_doi               10.1039/c5cc06322a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         {(C24H28N2O2)-(COC6H5)-Cl}-HCl
_chemical_formula_sum            'C31 H34 Cl2 N2 O3'
_chemical_formula_weight         553.50
_chemical_name_common            'DAC-COPh-Cl-HCl Cation'
_chemical_properties_physical    Hygroscopic
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2014-09-18 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.110(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4917(7)
_cell_length_b                   18.4515(14)
_cell_length_c                   16.3576(12)
_cell_measurement_temperature    100(2)
_cell_volume                     2820.3(4)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            52026
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.036
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexanes and dichloromethane'
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0336P)^2^+2.7157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4546
_reflns_number_total             4961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc06322a2.cif
_cod_data_source_block           2a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7124582
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details   none
_shelx_res_checksum              13369
_shelx_hkl_checksum              16393