N,N'-Dicyanoquinone diimide-derived donor-acceptor chromophores: conformational analysis and optoelectronic properties.
Chiu, Melanie; Jaun, Bernhard; Beels, Marten T. R.; Biaggio, Ivan; Gisselbrecht, Jean-Paul; Boudon, Corinne; Schweizer, W. Bernd; Kivala, Milan; Diederich, François; Organic letters 14 (2012) 54–57; doi:10.1021/ol202815q

data_1503483
_publ_section_title
;
 N,N'-Dicyanoquinone diimide-derived donor-acceptor chromophores:
 conformational analysis and optoelectronic properties.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              54
_journal_page_last               57
_journal_paper_doi               10.1021/ol202815q
_journal_volume                  14
_journal_year                    2012
_chemical_compound_source        'LOC ETH Zurich'
_chemical_formula_moiety         '2 (C24 H19 N5) , C7 H8 '
_chemical_formula_sum            'C55 H46 N10'
_chemical_formula_weight         847.043
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                89.683(8)
_cell_angle_beta                 78.116(9)
_cell_angle_gamma                74.635(13)
_cell_formula_units_Z            1
_cell_length_a                   7.2402(13)
_cell_length_b                   11.587(2)
_cell_length_c                   13.950(4)
_cell_measurement_reflns_used    17336
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.967
_cell_measurement_theta_min      2.910
_cell_volume                     1102.8(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.02586
_diffrn_orient_matrix_UB_12      0.10897
_diffrn_orient_matrix_UB_13      0.09455
_diffrn_orient_matrix_UB_21      -0.02161
_diffrn_orient_matrix_UB_22      0.03241
_diffrn_orient_matrix_UB_23      -0.08072
_diffrn_orient_matrix_UB_31      -0.06435
_diffrn_orient_matrix_UB_32      -0.03520
_diffrn_orient_matrix_UB_33      -0.00114
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.176
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            4418
_diffrn_reflns_theta_full        22.07
_diffrn_reflns_theta_max         22.07
_diffrn_reflns_theta_min         4.05
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             446.0
_exptl_crystal_size_max          .225
_exptl_crystal_size_mid          .06
_exptl_crystal_size_min          .003
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.267
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4418
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.267
_refine_ls_R_factor_all          0.2572
_refine_ls_R_factor_gt           0.1380
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2811
_refine_ls_wR_factor_ref         0.3595
_reflns_number_gt                2092
_reflns_number_total             4418
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202815q_si_002.cif
_cod_data_source_block           3d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1102.7(4)
_cod_original_sg_symbol_H-M      'P 1           '
_cod_original_formula_sum        'C55 H46 N10 '
_cod_database_code               1503483