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_1503482
_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( C728 H28 N6), C18 H20 N2, C1 H4 O'
_chemical_formula_sum            'C75 H80 N14 O'
_chemical_formula_weight         1193.562
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_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                100.552(2)
_cell_angle_beta                 98.525(2)
_cell_angle_gamma                96.793(3)
_cell_formula_units_Z            1
_cell_length_a                   11.5040(7)
_cell_length_b                   12.1136(7)
_cell_length_c                   12.8530(8)
_cell_measurement_reflns_used    25344
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.816
_cell_measurement_theta_min      2.910
_cell_volume                     1721.79(18)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.03972
_diffrn_orient_matrix_UB_12      -0.05531
_diffrn_orient_matrix_UB_13      0.05715
_diffrn_orient_matrix_UB_21      0.00168
_diffrn_orient_matrix_UB_22      0.04960
_diffrn_orient_matrix_UB_23      0.06892
_diffrn_orient_matrix_UB_31      -0.07425
_diffrn_orient_matrix_UB_32      0.03075
_diffrn_orient_matrix_UB_33      -0.00008
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.112
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6538
_diffrn_reflns_theta_full        20.85
_diffrn_reflns_theta_max         20.85
_diffrn_reflns_theta_min         4.06
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'red brown'
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cube
_exptl_crystal_F_000             636
_exptl_crystal_size_max          .105
_exptl_crystal_size_mid          .075
_exptl_crystal_size_min          .045
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.280
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.281
_refine_ls_R_factor_all          0.1624
_refine_ls_R_factor_gt           0.0988
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.001
_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          0.2314
_refine_ls_wR_factor_ref         0.2618
_reflns_number_gt                2119
_reflns_number_total             3565
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202815q_si_002.cif
_cod_data_source_block           3c
_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        1721.8(2)
_cod_original_sg_symbol_H-M      'P -1          '
_cod_original_formula_sum        'C75 H80 N14 O '
_cod_database_code               1503482