Expanding the chemical space for push-pull chromophores by non-concerted [2+2] and [4+2] cycloadditions: access to a highly functionalized 6,6-dicyanofulvene with an intense, low-energy charge-transfer band;
Govindasamy Jayamurugan; Jean-Paul Gisselbrecht; Corinne Boudon; Franziska Schoenebeck; W. Bernd Schweizer; Bruno Bernet; Francois Diederich; Chem.Commun. 47 (2011) 4520–; doi:10.1039/c1cc10247h

data_7106213
_publ_section_title
;
 Expanding the chemical space for push-pull chromophores by non-concerted
 [2+2] and [4+2] cycloadditions: access to a highly functionalized
 6,6-dicyanofulvene with an intense, low-energy charge-transfer band;
;
_journal_name_full               Chem.Commun.
_journal_page_first              4520
_journal_paper_doi               10.1039/c1cc10247h
_journal_volume                  47
_journal_year                    2011
_chemical_compound_source        'LOC ETH Zurich'
_chemical_formula_moiety         'C27 H21 N7 '
_chemical_formula_sum            'C27 H21 N7'
_chemical_formula_weight         443.514
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.2924(4)
_cell_length_b                   15.4265(7)
_cell_length_c                   25.3239(11)
_cell_measurement_reflns_used    356500
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.910
_cell_volume                     4411.5(3)
_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 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.07604
_diffrn_orient_matrix_UB_12      0.00970
_diffrn_orient_matrix_UB_13      -0.04434
_diffrn_orient_matrix_UB_21      -0.01541
_diffrn_orient_matrix_UB_22      -0.05058
_diffrn_orient_matrix_UB_23      -0.03749
_diffrn_orient_matrix_UB_31      -0.01793
_diffrn_orient_matrix_UB_32      0.02431
_diffrn_orient_matrix_UB_33      -0.02543
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.093
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7442
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.92
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            amber
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1856.0
_exptl_crystal_size_max          .33
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .03
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.249
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0699
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.002
_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          0.1766
_refine_ls_wR_factor_ref         0.1882
_reflns_number_gt                3026
_reflns_number_total             3818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10247h.txt
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      'P b c a '
_cod_original_formula_sum        'C27 H21 N7 '
_cod_database_code               7106213