Axially Chiral Bichromophoric Fluorescent Dyes
Heinz Langhals; Alexander Hofer; Stefan Bernhard; Jay S. Siegel; Peter Mayer; Journal of Organic Chemistry 76 (2011) 990–992; doi:10.1021/jo102254a

data_4026033
_publ_contact_author_address
;
Department Chemie
Ludwig-Maximilians Universit\"at
Butenandtstra\&se 5-13 (Haus F)
D-81377 M\"unchen
Bundesrepublik Deutschland
;
_publ_contact_author_name        'Heinz Langhals'
_publ_section_title
;
 Axially Chiral Bichromophoric Fluorescent Dyes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              990
_journal_page_last               992
_journal_paper_doi               10.1021/jo102254a
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C14 H16 N2'
_chemical_formula_sum            'C14 H16 N2'
_chemical_formula_weight         212.290
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'P. Mayer'
_audit_block_code                C14H16N2_oo187_langhals
_audit_creation_date
;
'Mon Oct 18 15:10:30 2010'
;
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             19-Oct-10
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4997(4)
_cell_length_b                   7.9251(4)
_cell_length_c                   19.9447(11)
_cell_measurement_reflns_used    2029
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.2491
_cell_measurement_theta_min      4.2496
_cell_volume                     1185.43(11)
_computing_cell_refinement
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
<i>Acta Cryst.</i> A<b>64</b>, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -41.00   47.00   1.0000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931   50.0000 -131.0000 88

  2 omega  -93.00   13.00   1.0000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931  -77.0000   90.0000 106

  3 omega   25.00   79.00   1.0000   27.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2306   77.0000  -60.0000 54

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0685460347
_diffrn_orient_matrix_UB_12      0.0492302726
_diffrn_orient_matrix_UB_13      -0.0146908665
_diffrn_orient_matrix_UB_21      0.0586345345
_diffrn_orient_matrix_UB_22      0.0233074393
_diffrn_orient_matrix_UB_23      -0.0262834666
_diffrn_orient_matrix_UB_31      -0.0283705742
_diffrn_orient_matrix_UB_32      -0.0708351088
_diffrn_orient_matrix_UB_33      -0.0188677466
_diffrn_radiation_collimation    '0.5 mm collimator'
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5114
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         4.26
_diffrn_source_current           40_mA
_diffrn_source_power             2.00_kW
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50_kV
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.18951(11)
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.919
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0403P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0740
_reflns_number_gt                1017
_reflns_number_total             1409
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102254a_si_002.cif
_cod_data_source_block           oo187
_cod_database_code               4026033