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_7150616
_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         'C20 H16 Br N3 '
_chemical_formula_sum            'C20 H16 Br N3'
_chemical_formula_weight         378.273
_chemical_name_common
;(E)-2-(3-(4-bromophenyl)-1-(4-
(dimethylamino)phenyl)allylidene)malononitrile
;
_chemical_name_systematic
;
(E)-2-(3-(4-bromophenyl)-1-(4-(dimethylamino)phenyl)allylidene)malononitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 93.4125(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4778(3)
_cell_length_b                   7.9420(3)
_cell_length_c                   24.0757(9)
_cell_measurement_reflns_used    28352
_cell_measurement_temperature    223
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.425
_cell_volume                     1809.03(11)
_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 0.893
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.04027
_diffrn_orient_matrix_UB_12      -0.09212
_diffrn_orient_matrix_UB_13      -0.03263
_diffrn_orient_matrix_UB_21      -0.04075
_diffrn_orient_matrix_UB_22      0.02356
_diffrn_orient_matrix_UB_23      -0.11679
_diffrn_orient_matrix_UB_31      0.03692
_diffrn_orient_matrix_UB_32      0.01667
_diffrn_orient_matrix_UB_33      -0.00952
_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       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            6188
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.42
_exptl_absorpt_coefficient_mu    2.277
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.001
_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          0.1464
_refine_ls_wR_factor_ref         0.1684
_reflns_number_gt                2650
_reflns_number_total             3690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b821230a.txt
_cod_data_source_block           3e
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 21/c '
_cod_original_formula_sum        'C20 H16 Br N3 '
_cod_database_code               7150616