Anion-π Complexes of Halides with p-Benzoquinones: Structures, Thermodynamics, and Criteria of Charge Transfer to Electron Transfer Transition.
Kepler, Slade; Zeller, Matthias; Rosokha, Sergiy V.; Journal of the American Chemical Society 141 (2019) 9338–9348; doi:10.1021/jacs.9b03277

data_4128736
_publ_section_title
;
 Anion-\p Complexes of Halides with p-Benzoquinones: Structures,
 Thermodynamics, and Criteria of Charge Transfer to Electron Transfer
 Transition.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9338
_journal_page_last               9348
_journal_paper_doi               10.1021/jacs.9b03277
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         '2(C8 Cl2 N2 O2), C12 H28 N, Cl'
_chemical_formula_sum            'C28 H28 Cl5 N5 O4'
_chemical_formula_weight         675.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 96.098(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2745(13)
_cell_length_b                   10.2019(9)
_cell_length_c                   20.6506(18)
_cell_measurement_reflns_used    8348
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.273
_cell_measurement_theta_min      2.682
_cell_volume                     3199.8(5)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'SAINT V7.23A (Bruker, 2005)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
Olex2 (Dolomanov et al., 2009)
SHELXLE Rev946 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0978
_diffrn_reflns_av_unetI/netI     0.1252
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38981
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.092
_diffrn_reflns_theta_min         3.026
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0644 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.8369.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         9320
_refine_ls_number_restraints     424
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1531
_refine_ls_R_factor_gt           0.0613
_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^)+(0.0429P)^2^+0.2478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4835
_reflns_number_total             9320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b03277_si_002.cif
_cod_data_source_block           cx0501
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4128736
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.900
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              70810
_shelx_hkl_checksum              58950