Quadrupolar benzobisthiazole-cored arylamines as highly efficient two-photon absorbing fluorophores.
Hrobárik, Peter; Hrobáriková, Veronika; Semak, Vladislav; Kasák, Peter; Rakovský, Erik; Polyzos, Ioannis; Fakis, Mihalis; Persephonis, Peter; Organic letters 16 (2014) 6358–6361; doi:10.1021/ol503137p

data_1518389
_publ_section_title
;
 Quadrupolar benzobisthiazole-cored arylamines as highly efficient
 two-photon absorbing fluorophores.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6358
_journal_page_last               6361
_journal_paper_doi               10.1021/ol503137p
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C48 H34 N4 S2, 2(C H Cl3)'
_chemical_formula_sum            'C50 H36 Cl6 N4 S2'
_chemical_formula_weight         969.65
_chemical_name_systematic
;
(E,E)-2,6-Bis{2-[4-(N,N-diphenylamino)phenyl]ethenyl}benzo[1,2-d:4,5-d']
bisthiazole
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-22
_audit_creation_method
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Olex2 1.2-alpha
(compiled 2014.09.19 svn.r3012 for OlexSys, GUI svn.r4889)
;
_cell_angle_alpha                101.686(4)
_cell_angle_beta                 91.082(4)
_cell_angle_gamma                107.507(5)
_cell_formula_units_Z            2
_cell_length_a                   9.7874(5)
_cell_length_b                   11.8977(6)
_cell_length_c                   22.0108(11)
_cell_measurement_reflns_used    5094
_cell_measurement_temperature    298
_cell_measurement_theta_max      18.7280
_cell_measurement_theta_min      3.6880
_cell_volume                     2385.0(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'ShelXL 2014/6 (Sheldrick, 2008)'
_computing_structure_solution    'SIR 2008 (Burla et al., 2007)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4340
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle \k-axis diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1353
_diffrn_reflns_av_sigmaI/netI    0.1279
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            38253
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        18.846
_diffrn_reflns_theta_max         18.846
_diffrn_reflns_theta_min         3.711
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.487
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.34 
 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       prism
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.5445
_exptl_crystal_size_mid          0.0598
_exptl_crystal_size_min          0.0418
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     610
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     745
_refine_ls_restrained_S_all      1.246
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0938
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1505P)^2^+5.1655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2475
_refine_ls_wR_factor_ref         0.2687
_reflns_number_gt                2805
_reflns_number_total             3708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503137p_si_002.cif
_cod_data_source_block           PK439
_cod_depositor_comments          'Adding full bibliography for 1518389.cif.'
_cod_database_code               1518389
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H44 of C44, H24 of C24, H25 of C25, H28 of C28, H27 of C27, H21 of C21, H22
  of C22, H19 of C19, H17 of C17, H16 of C16, H13 of C13, H14 of C14, H6 of C6,
  H12 of C12, H50 of C50, H46 of C46, H31 of C31, H42 of C42, H20 of C20, H53
  of C53, H48 of C48, H45 of C45, H54 of C54, H39 of C39, H41 of C41, H40 of
  C40, H38 of C38, H32 of C32, H34 of C34, H33 of C33, H51 of C51, H52 of C52,
  H47 of C47, H35 of C35
 At 1.5 times of:
  H1B of C1B, H1A of C1A
2. Restrained distances
 S1-C5 \\sim S10-C11
 with sigma of 0.01
 S1-C2 \\sim S10-C9
 with sigma of 0.01
 N3-C2 \\sim N8-C9
 with sigma of 0.01
 N3-C4 \\sim N8-C7
 with sigma of 0.01
 C7-C6 \\sim C4-C12
 with sigma of 0.01
 C6-C5 \\sim C12-C11
 with sigma of 0.01
 C5-C4 \\sim C7-C11
 with sigma of 0.01
 C2-C13 \\sim C9-C21
 with sigma of 0.01
 C14-C13 \\sim C22-C21
 with sigma of 0.01
 C15-C14 \\sim C23-C22
 with sigma of 0.01
 C20-C15 \\sim C16-C15 \\sim C24-C23 \\sim C28-C23
 with sigma of 0.01
 C20-C19 \\sim C17-C16 \\sim C25-C24 \\sim C28-C27
 with sigma of 0.01
 C19-C18 \\sim C18-C17 \\sim C26-C25 \\sim C27-C26
 with sigma of 0.01
 N29-C18 \\sim N36-C26
 with sigma of 0.01
 N29-C30 \\sim N36-C37
 with sigma of 0.01
 N29-C43 \\sim N36-C49
 with sigma of 0.01
 C35-C30 \\sim C31-C30 \\sim C48-C43 \\sim C44-C43 \\sim C50-C49 \\sim C54-C49
\\sim C38-C37 \\sim C42-C37
 with sigma of 0.01
 C35-C34 \\sim C32-C31 \\sim C48-C47 \\sim C45-C44 \\sim C51-C50 \\sim C54-C53
\\sim C39-C38 \\sim C42-C41
 with sigma of 0.01
 C34-C33 \\sim C33-C32 \\sim C47-C46 \\sim C46-C45 \\sim C52-C51 \\sim C53-C52
\\sim C40-C39 \\sim C41-C40
 with sigma of 0.01
 Cl1B-Cl2B \\sim Cl2B-Cl3B \\sim Cl3B-Cl1B \\sim Cl4B-Cl5B \\sim Cl5B-Cl6B
\\sim Cl6B-Cl4B
 with sigma of 0.01
 Cl1A-Cl2A \\sim Cl2A-Cl3A \\sim Cl3A-Cl1A \\sim Cl4A-Cl5A \\sim Cl5A-Cl6A
\\sim Cl6A-Cl4A
 with sigma of 0.01
 Cl6B-C1B \\sim Cl3B-C1B \\sim Cl2B-C1B \\sim Cl5B-C1B \\sim Cl4B-C1B \\sim
Cl1B-C1B \\sim Cl5A-C1A ~
 Cl3A-C1A \\sim Cl6A-C1A \\sim Cl1A-C1A \\sim Cl4A-C1A \\sim Cl2A-C1A
 with sigma of 0.01
3. Restrained planarity
 Cl1B, Cl2B, Cl3B, Cl4B, Cl5B, Cl6B
 with sigma of 0.1
 Cl5A, Cl3A, Cl6A, Cl1A, Cl4A, Cl2A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Cl4B \\sim Cl1B \\sim Cl3B \\sim Cl6B \\sim Cl2B \\sim Cl5B: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
Cl5A \\sim Cl3A \\sim Cl6A \\sim Cl1A \\sim Cl4A \\sim Cl2A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(Cl5B)=Sof(Cl4B)=Sof(Cl6B)=1-FVAR(1)
 Sof(Cl1B)=Sof(Cl2B)=Sof(Cl3B)=FVAR(1)
 Sof(Cl1A)=Sof(Cl3A)=Sof(Cl2A)=1-FVAR(2)
 Sof(Cl6A)=Sof(Cl4A)=Sof(Cl5A)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C1B(H1B), C1A(H1A)
7.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C6(H6), C14(H14), C13(H13), C16(H16), C17(H17), C19(H19), C22(H22),
 C21(H21), C27(H27), C28(H28), C25(H25), C24(H24), C44(H44), C50(H50), C42(H42),
  C20(H20), C48(H48), C45(H45), C54(H54), C39(H39), C53(H53), C40(H40),
 C41(H41), C38(H38), C46(H46), C31(H31), C47(H47), C35(H35), C52(H52), C51(H51),
  C33(H33), C34(H34), C32(H32)
;