Dimerization of Merocyanine Dyes. Structural and Energetic Characterization of Dipolar Dye Aggregates and Implications for Nonlinear Optical Materials
Frank Würthner; Sheng Yao; Tony Debaerdemaeker; Rüdiger Wortmann; Journal of the American Chemical Society 124 (2002) 9431–9447; doi:10.1021/ja020168f

data_4115018
_publ_contact_author_address
;       Universit\"at Ulm
 Abteilung Organische Chemie II
 Albert-Einstein-Allee 11
 89081 ULm
 Germany
;
_publ_contact_author_email       frank.wuerthner@chemie.uni-ulm.de
_publ_contact_author_fax         '049 731 5022840'
_publ_contact_author_name        'Frank W\"urthner'
_publ_contact_author_phone       '049 731 5022849'
_publ_section_title
;
 Dimerization of Merocyanine Dyes. Structural and Energetic
 Characterization of Dipolar Dye Aggregates and Implications for Nonlinear
 Optical Materials
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9431
_journal_page_last               9447
_journal_paper_doi               10.1021/ja020168f
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C26 H37 N3 O2 S'
_chemical_formula_weight         455.65
_chemical_melting_point          419(1)
_chemical_name_common
; (5-Ethylbutylamino-3,4-diethyl-thiophen)-2-ylmethylene-4-
  methyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.27(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.574(1)
_cell_length_b                   23.833(2)
_cell_length_c                   12.382(1)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.07
_cell_measurement_theta_min      1.87
_cell_volume                     2503.9(4)
_computing_cell_refinement       'STOE IPDS'
_computing_data_collection       'STOE IPDS'
_computing_data_reduction        'STOE IPDS'
_computing_molecular_graphics    'Platon, Ortep'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'XMY-93 (Debaerdemaeker, 1993)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 0.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'STOE IPDS, Image Plate'
_diffrn_measurement_method       rotation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18814
_diffrn_reflns_theta_full        24.15
_diffrn_reflns_theta_max         24.15
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.44(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         7865
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                5908
_reflns_number_total             7865
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja020168f_2.cif
_cod_data_source_block           yao236
_cod_original_cell_volume        2503.8(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4115018