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_7106214
_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         '2(C26 H20 N6), C H Cl3 '
_chemical_formula_sum            'C53 H41 Cl3 N6'
_chemical_formula_weight         868.312
_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                102.4170(13)
_cell_angle_beta                 90.4984(13)
_cell_angle_gamma                103.9678(13)
_cell_formula_units_Z            1
_cell_length_a                   9.1282(3)
_cell_length_b                   11.1896(3)
_cell_length_c                   12.4251(4)
_cell_measurement_reflns_used    31360
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1200.32(6)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.04066
_diffrn_orient_matrix_UB_12      -0.09817
_diffrn_orient_matrix_UB_13      0.03879
_diffrn_orient_matrix_UB_21      0.00936
_diffrn_orient_matrix_UB_22      -0.05970
_diffrn_orient_matrix_UB_23      -0.07264
_diffrn_orient_matrix_UB_31      0.07500
_diffrn_orient_matrix_UB_32      -0.03233
_diffrn_orient_matrix_UB_33      0.01220
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9624
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.85
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cube
_exptl_crystal_F_000             494.0
_exptl_crystal_size_max          .27
_exptl_crystal_size_mid          .24
_exptl_crystal_size_min          .21
_refine_diff_density_max         1.038
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.710
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5472
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      3.537
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0714
_refine_ls_shift/su_max          0.012
_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          0.2208
_refine_ls_wR_factor_ref         0.2329
_reflns_number_gt                4453
_reflns_number_total             5472
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10247h.txt
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C53 H41 Cl3 N6 '
_cod_database_code               7106214