Benzodipyrrole-2,6-dione-3,7-diylidenedimalononitrile Derivatives for Air-Stable <i>n</i>-Type Organic Field-Effect Transistors: Critical Role of <i>N</i>-Alkyl Substituent on Device Performance.
Dhondge, Attrimuni P.; Huang, Yi-Xiang; Lin, Ta; Hsu, Yu-Hung; Tseng, Shin-Lun; Chang, Yu-Chang; Chen, Henry J. H.; Kuo, Ming-Yu; The Journal of organic chemistry 84 (2019) 14061–14068; doi:10.1021/acs.joc.9b02207

data_4033628
_publ_section_title
;
 Benzodipyrrole-2,6-dione-3,7-diylidenedimalononitrile Derivatives for
 Air-Stable <i>n</i>-Type Organic Field-Effect Transistors: Critical Role
 of <i>N</i>-Alkyl Substituent on Device Performance.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14061
_journal_page_last               14068
_journal_paper_doi               10.1021/acs.joc.9b02207
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_sum            'C24 H20 N6 O2'
_chemical_formula_weight         424.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 96.536(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3720(9)
_cell_length_b                   10.1969(10)
_cell_length_c                   11.3176(11)
_cell_measurement_reflns_used    6759
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.4134
_cell_measurement_theta_min      2.6966
_cell_volume                     1074.54(18)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12598
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.436
_diffrn_reflns_theta_min         2.187
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.7953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lamellar
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1471 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4040
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0517P)^2^+0.2577P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.864
_reflns_Friedel_fraction_max     0.860
_reflns_number_gt                3531
_reflns_number_total             4040
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02207_si_002.cif
_cod_data_source_block           180602LT_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'RM' changed to 'rm'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033628--4033629.cif.
;
_cod_database_code               4033628
_shelxl_version_number           2014/6
_shelx_res_checksum              4473
_shelx_hkl_checksum              63470