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_1513470
_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         'C32 H36 F6 N2 O4'
_chemical_formula_sum            'C32 H36 F6 N2 O4'
_chemical_formula_weight         626.63
_chemical_name_common            bis(CF3)NDI
_chemical_name_systematic
;
N,N'-(n-octyl)-2,6-trifluoromethyl-
1,4,5,8-naphthalenetetracarboxylic 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                85.639(4)
_cell_angle_beta                 82.595(4)
_cell_angle_gamma                81.820(4)
_cell_formula_units_Z            1
_cell_length_a                   4.9874(7)
_cell_length_b                   8.9169(13)
_cell_length_c                   16.946(2)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.06
_cell_measurement_theta_min      5.02
_cell_volume                     738.46(17)
_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 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  prospector
_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  0.0184
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13194
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.061
_diffrn_reflns_theta_min         5.019
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.009
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0914 before and 0.0288 after correction.
The Ratio of minimum to maximum transmission is 0.9057.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0283
_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^)+(0.0423P)^2^+0.2458P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2603
_reflns_number_total             2646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol403736m_si_002.cif
_cod_data_source_block           cf3ndi
_cod_original_cell_volume        738.47(18)
_cod_database_code               1513470
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.775
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              30997
_shelx_hkl_checksum              1918