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_7106215
_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(C25 H21 N5 ), 0.5( C2 H4 Cl2) '
_chemical_formula_sum            'C51 H44 Cl N10'
_chemical_formula_weight         832.436
_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                93.245(5)
_cell_angle_beta                 91.748(5)
_cell_angle_gamma                109.113(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8044(6)
_cell_length_b                   12.8651(10)
_cell_length_c                   18.011(2)
_cell_measurement_reflns_used    168410
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.753
_cell_volume                     2140.2(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 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.04421
_diffrn_orient_matrix_UB_12      0.09140
_diffrn_orient_matrix_UB_13      0.03710
_diffrn_orient_matrix_UB_21      -0.04176
_diffrn_orient_matrix_UB_22      0.06452
_diffrn_orient_matrix_UB_23      -0.02992
_diffrn_orient_matrix_UB_31      -0.03479
_diffrn_orient_matrix_UB_32      0.00263
_diffrn_orient_matrix_UB_33      0.04340
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11481
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             874
_exptl_crystal_size_max          .24
_exptl_crystal_size_mid          .075
_exptl_crystal_size_min          .009
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.532
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     570
_refine_ls_number_reflns         7214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.532
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0742
_refine_ls_shift/su_max          0.050
_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          0.2097
_refine_ls_wR_factor_ref         0.2206
_reflns_number_gt                5920
_reflns_number_total             7214
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10247h.txt
_cod_data_source_block           7
_cod_original_cell_volume        2140.3(3)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C51 H44 Cl N10 '
_cod_database_code               7106215