Enantiopure versus racemic naphthalene diimide-based n-type organic semiconductors: effect on charge transport
Chen, Ming; Li, Jing; Jiao, Xuechen; Yang, Xiaochun; Wu, Wenting; McNeill, Christopher R.; Gao, Xike; Journal of Materials Chemistry C 7 (2019) 2659–; doi:10.1039/C8TC06273K

data_7237606
_publ_section_title
;
 Enantiopure versus racemic naphthalene diimide-based n-type organic
 semiconductors: effect on charge transport
;
_journal_issue                   9
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2659
_journal_paper_doi               10.1039/C8TC06273K
_journal_volume                  7
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H28 N2 O4'
_chemical_formula_weight         468.53
_chemical_name_systematic
(R)-2-hexyl-7-(2-phenylpropyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-01-15 deposited with the CCDC.	2019-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                89.9140(10)
_cell_angle_beta                 86.0960(10)
_cell_angle_gamma                82.5490(10)
_cell_formula_units_Z            1
_cell_length_a                   4.8296(2)
_cell_length_b                   8.7435(3)
_cell_length_c                   14.4477(5)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.099
_cell_measurement_theta_min      10.203
_cell_volume                     603.52(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17553
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.493
_diffrn_reflns_theta_min         5.102
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 1856 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0526
_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^)+(0.1019P)^2^+0.0524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1564
_reflns_Friedel_coverage         0.967
_reflns_Friedel_fraction_full    0.926
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                3943
_reflns_number_total             4116
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8tc06273k2.cif
_cod_data_source_block           d8v18583
_cod_database_code               7237606
_shelx_estimated_absorpt_t_min   0.879
_shelx_estimated_absorpt_t_max   0.934
_shelxl_version_number           2013-4
_shelx_res_checksum              33095