New donor–acceptor chromophores by formal [2+2] cycloaddition of donor-substituted alkynes to dicyanovinyl derivatives
Jarowski, Peter D.; Wu, Yi-Lin; Boudon, Corinne; Gisselbrecht, Jean-Paul; Gross, Maurice; Schweizer, W. Bernd; Diederich, François; Organic & Biomolecular Chemistry 7 (2009) 1312–1322; doi:10.1039/b821230a

data_7150617
_publ_section_title
;
 New donor--acceptor chromophores by formal [2+2] cycloaddition of
 donor-substituted alkynes to dicyanovinyl derivatives
;
_journal_issue                   7
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1312
_journal_page_last               1322
_journal_paper_doi               10.1039/b821230a
_journal_volume                  7
_journal_year                    2009
_chemical_compound_source        'LOC ETH Zurich'
_chemical_formula_moiety         'C21 H19 N3 O '
_chemical_formula_sum            'C21 H19 N3 O'
_chemical_formula_weight         329.403
_chemical_name_common
;2-(1-(4-(dimethylamino)phenyl)-3-(4-
methoxyphenyl)allylidene)propanedinitrile
;
_chemical_name_systematic
;
2-(1-(4-(dimethylamino)phenyl)-3-(4-methoxyphenyl)allylidene)propanedinitrile
;
_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                104.702(2)
_cell_angle_beta                 90.581(2)
_cell_angle_gamma                104.638(2)
_cell_formula_units_Z            4
_cell_length_a                   7.8176(2)
_cell_length_b                   15.0473(4)
_cell_length_c                   16.0532(5)
_cell_measurement_reflns_used    16543
_cell_measurement_temperature    203
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.425
_cell_volume                     1761.71(9)
_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, 1997)'
_computing_structure_solution    'SIR97(Altomare et al., J. Appl. Cryst.,1999)'
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.09883
_diffrn_orient_matrix_UB_12      0.04275
_diffrn_orient_matrix_UB_13      0.07743
_diffrn_orient_matrix_UB_21      -0.00857
_diffrn_orient_matrix_UB_22      -0.03408
_diffrn_orient_matrix_UB_23      0.06196
_diffrn_orient_matrix_UB_31      0.03460
_diffrn_orient_matrix_UB_32      -0.05429
_diffrn_orient_matrix_UB_33      -0.00540
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10655
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Cinnabar
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696.0
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .006
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         6111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_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          0.1259
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                4731
_reflns_number_total             6111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b821230a.txt
_cod_data_source_block           3g
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C21 H19 N3 O '
_cod_database_code               7150617