Radical anions of trifluoromethylated perylene and naphthalene imide and diimide electron acceptors.
Roznyatovskiy, Vladimir V.; Gardner, Daniel M.; Eaton, Samuel W.; Wasielewski, Michael R.; Organic letters 16 (2014) 696–699; doi:10.1021/ol403736m

data_1513469
_publ_section_title
;
 Radical anions of trifluoromethylated perylene and naphthalene imide and
 diimide electron acceptors.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              696
_journal_page_last               699
_journal_paper_doi               10.1021/ol403736m
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C38 H28 F6 N2 O4'
_chemical_formula_sum            'C38 H28 F6 N2 O4'
_chemical_formula_weight         690.62
_chemical_name_common            bis(CF3)PDI
_chemical_name_systematic
;
N,N'-(1-cyclohexyl)-1,7-(trifluoromethyl)
perylenetetracarboxylic diimide
;
_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     direct
_audit_creation_date             2013-12-23
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                97.378(3)
_cell_angle_beta                 98.233(3)
_cell_angle_gamma                107.436(3)
_cell_formula_units_Z            2
_cell_length_a                   11.1314(8)
_cell_length_b                   11.2899(8)
_cell_length_c                   12.8198(8)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.93
_cell_measurement_theta_min      3.54
_cell_volume                     1495.98(18)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13042
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.928
_diffrn_reflns_theta_min         3.542
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.067
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0507 before and 0.0257 after correction.
The Ratio of minimum to maximum transmission is 0.9157.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0280
_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^)+(0.0388P)^2^+0.5683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0765
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4791
_reflns_number_total             5196
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol403736m_si_002.cif
_cod_data_source_block           cf3pdi
_cod_database_code               1513469
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.885
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C20(H20A,
 H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C14(H14), C28(H28), C32(H32), C33(H33)
;
_shelx_res_checksum              25837
_shelx_hkl_checksum              55516