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_4033629
_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_formula_sum            'C32 H36 N6 O2'
_chemical_formula_weight         536.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 94.380(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6764(7)
_cell_length_b                   11.0515(9)
_cell_length_c                   31.064(2)
_cell_measurement_reflns_used    8159
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3328
_cell_measurement_theta_min      2.6304
_cell_volume                     2969.9(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0288
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            24500
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         1.315
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lamellar
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0584P)^2^+0.5229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4953
_reflns_number_total             6074
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02207_si_003.cif
_cod_data_source_block           180349lt_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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.
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_cod_original_cell_volume        2970.0(4)
_cod_database_code               4033629
_shelxl_version_number           2014/6
_shelx_res_checksum              36648
_shelx_hkl_checksum              16673