# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2004



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_year                    ?
_journal_page_first              ?

_publ_contact_author_name        'Tong-Ing Ho'
_publ_contact_author_address     
;
Department of Chemistry
National Taiwan Universtiy
No. 1, Sec. 4, Roosevelt Road
Taipei
Taipei
106
TAIWAN
;

_publ_contact_author_email       HALL@NTU.EDU.TW

_publ_section_title              
;
Arylethynylacridines: Electrochemiluminescence and
photophysical properties
;
loop_
_publ_author_name
'Tong-Ing Ho.'
'Hsing-Hua Chiu.'
'Arumugasamy Elangovan'
'Shu-Wen Yang.'

data_ic10594
_database_code_depnum_ccdc_archive 'CCDC 244931'

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            
9-[4-(N,N-Dimethylamino)phenyl]ethynyl-acridine
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C23 H18 N2'
_chemical_formula_weight         322.39
_chemical_melting_point          ?
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2870(2)
_cell_length_b                   9.3930(2)
_cell_length_c                   10.7350(3)
_cell_angle_alpha                81.7260(10)
_cell_angle_beta                 72.9830(10)
_cell_angle_gamma                71.805(2)
_cell_volume                     849.25(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    16227
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  0.988

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5997
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         27.45
_reflns_number_total             3827
_reflns_number_observed          2855
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       'COLLECT (Nonius BV)'
_computing_cell_refinement       'HKL Denzo & Scalepack (Otwinowski & Minor)'
_computing_data_reduction        'HKL Denzo & Scalepack (Otwinowski & Minor)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 28 with very negative F^2^
or flagged by the user for potential systematic errors.  Weighted R-factors
wR and all goodnesses of fit S are based on F^2^, conventional R-factors R
are based on F, with F set to zero for negative F^2^. The observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.1188P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0175(166)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3799
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_obs          0.0483
_refine_ls_wR_factor_all         0.1449
_refine_ls_wR_factor_obs         0.1278
_refine_ls_goodness_of_fit_all   1.023
_refine_ls_goodness_of_fit_obs   1.067
_refine_ls_restrained_S_all      1.035
_refine_ls_restrained_S_obs      1.067
_refine_ls_shift/esd_max         0.007
_refine_ls_shift/esd_mean        0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.59394(14) 0.76747(13) 0.43201(12) 0.0558(3) Uani 1 d . .
N2 N 0.2235(2) -0.04113(14) 0.02629(13) 0.0646(4) Uani 1 d . .
C1 C 0.7001(2) 0.66305(15) 0.35291(13) 0.0508(3) Uani 1 d . .
C2 C 0.8624(2) 0.6548(2) 0.3261(2) 0.0668(4) Uani 1 d . .
H2A H 0.8915(2) 0.7205(2) 0.3643(2) 0.080 Uiso 1 calc R .
C3 C 0.9739(2) 0.5535(2) 0.2464(2) 0.0737(5) Uani 1 d . .
H3A H 1.0789(2) 0.5500(2) 0.2305(2) 0.088 Uiso 1 calc R .
C4 C 0.9338(2) 0.4526(2) 0.1865(2) 0.0691(4) Uani 1 d . .
H4A H 1.0122(2) 0.3838(2) 0.1311(2) 0.083 Uiso 1 calc R .
C5 C 0.7813(2) 0.4551(2) 0.20935(15) 0.0583(4) Uani 1 d . .
H5A H 0.7563(2) 0.3878(2) 0.16939(15) 0.070 Uiso 1 calc R .
C6 C 0.65960(15) 0.55923(14) 0.29358(12) 0.0466(3) Uani 1 d . .
C7 C 0.5001(2) 0.56488(13) 0.32277(12) 0.0453(3) Uani 1 d . .
C8 C 0.38803(15) 0.67089(14) 0.40847(12) 0.0463(3) Uani 1 d . .
C9 C 0.2249(2) 0.6826(2) 0.44663(14) 0.0558(4) Uani 1 d . .
H9A H 0.1884(2) 0.6172(2) 0.41502(14) 0.067 Uiso 1 calc R .
C10 C 0.1222(2) 0.7879(2) 0.5284(2) 0.0666(4) Uani 1 d . .
H10A H 0.0160(2) 0.7937(2) 0.5531(2) 0.080 Uiso 1 calc R .
C11 C 0.1752(2) 0.8889(2) 0.5765(2) 0.0703(4) Uani 1 d . .
H11A H 0.1030(2) 0.9615(2) 0.6318(2) 0.084 Uiso 1 calc R .
C12 C 0.3289(2) 0.8818(2) 0.54375(15) 0.0636(4) Uani 1 d . .
H12A H 0.3613(2) 0.9495(2) 0.57656(15) 0.076 Uiso 1 calc R .
C13 C 0.4419(2) 0.77174(15) 0.45939(13) 0.0503(3) Uani 1 d . .
C14 C 0.4526(2) 0.46297(15) 0.26714(13) 0.0508(3) Uani 1 d . .
C15 C 0.4128(2) 0.37623(15) 0.22257(14) 0.0513(3) Uani 1 d . .
C16 C 0.36525(14) 0.26997(14) 0.17219(13) 0.0481(3) Uani 1 d . .
C17 C 0.3622(2) 0.2802(2) 0.04252(14) 0.0538(3) Uani 1 d . .
H17A H 0.3916(2) 0.3578(2) -0.01284(14) 0.065 Uiso 1 calc R .
C18 C 0.3168(2) 0.1784(2) -0.00587(13) 0.0540(3) Uani 1 d . .
H18A H 0.3158(2) 0.1888(2) -0.09311(13) 0.065 Uiso 1 calc R .
C19 C 0.27193(15) 0.05932(14) 0.07372(13) 0.0478(3) Uani 1 d . .
C20 C 0.2765(2) 0.0488(2) 0.20443(14) 0.0544(3) Uani 1 d . .
H20A H 0.2484(2) -0.0293(2) 0.25998(14) 0.065 Uiso 1 calc R .
C21 C 0.3216(2) 0.1516(2) 0.25183(14) 0.0543(3) Uani 1 d . .
H21A H 0.3230(2) 0.1420(2) 0.33894(14) 0.065 Uiso 1 calc R .
C22 C 0.2250(2) -0.0320(2) -0.1091(2) 0.0722(5) Uani 1 d . .
H22A H 0.1879(2) -0.1107(2) -0.1246(2) 0.108 Uiso 1 calc R .
H22B H 0.3303(2) -0.0428(2) -0.1626(2) 0.108 Uiso 1 calc R .
H22C H 0.1579(2) 0.0636(2) -0.1303(2) 0.108 Uiso 1 calc R .
C23 C 0.2039(2) -0.1769(2) 0.1013(2) 0.0783(5) Uani 1 d . .
H23A H 0.1700(2) -0.2333(2) 0.0533(2) 0.117 Uiso 1 calc R .
H23B H 0.1264(2) -0.1521(2) 0.1827(2) 0.117 Uiso 1 calc R .
H23C H 0.3021(2) -0.2360(2) 0.1178(2) 0.117 Uiso 1 calc R .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0651(7) 0.0548(7) 0.0568(7) -0.0023(5) -0.0226(6) -0.0246(6)
N2 0.0900(9) 0.0590(7) 0.0598(8) -0.0030(6) -0.0280(7) -0.0347(7)
C1 0.0574(8) 0.0490(7) 0.0527(8) 0.0069(6) -0.0213(6) -0.0225(6)
C2 0.0622(9) 0.0654(9) 0.0858(11) 0.0032(8) -0.0292(8) -0.0306(7)
C3 0.0507(8) 0.0725(10) 0.0987(13) 0.0042(9) -0.0189(8) -0.0234(8)
C4 0.0540(8) 0.0647(9) 0.0792(11) -0.0031(8) -0.0113(7) -0.0100(7)
C5 0.0618(8) 0.0521(8) 0.0621(9) -0.0027(6) -0.0193(7) -0.0153(6)
C6 0.0527(7) 0.0452(7) 0.0461(7) 0.0054(5) -0.0188(6) -0.0179(5)
C7 0.0556(7) 0.0442(7) 0.0431(7) 0.0059(5) -0.0215(6) -0.0198(5)
C8 0.0543(7) 0.0478(7) 0.0408(7) 0.0047(5) -0.0189(5) -0.0173(6)
C9 0.0560(8) 0.0638(8) 0.0522(8) 0.0023(6) -0.0192(6) -0.0213(7)
C10 0.0545(8) 0.0821(11) 0.0580(9) -0.0009(8) -0.0125(7) -0.0158(7)
C11 0.0729(10) 0.0730(10) 0.0549(9) -0.0122(7) -0.0117(7) -0.0077(8)
C12 0.0785(10) 0.0609(9) 0.0540(9) -0.0102(7) -0.0196(7) -0.0187(7)
C13 0.0617(8) 0.0504(7) 0.0438(7) 0.0026(5) -0.0202(6) -0.0194(6)
C14 0.0556(7) 0.0508(7) 0.0515(8) 0.0015(6) -0.0206(6) -0.0188(6)
C15 0.0503(7) 0.0514(7) 0.0560(8) -0.0030(6) -0.0181(6) -0.0159(6)
C16 0.0446(6) 0.0480(7) 0.0546(8) -0.0062(6) -0.0152(6) -0.0140(5)
C17 0.0620(8) 0.0530(7) 0.0521(8) 0.0047(6) -0.0182(6) -0.0248(6)
C18 0.0645(8) 0.0574(8) 0.0447(7) -0.0003(6) -0.0175(6) -0.0220(6)
C19 0.0483(7) 0.0462(7) 0.0511(7) -0.0056(6) -0.0144(6) -0.0142(5)
C20 0.0652(8) 0.0539(8) 0.0493(8) 0.0041(6) -0.0162(6) -0.0266(6)
C21 0.0627(8) 0.0604(8) 0.0461(7) -0.0016(6) -0.0172(6) -0.0242(6)
C22 0.0882(11) 0.0719(10) 0.0691(10) -0.0131(8) -0.0349(9) -0.0232(9)
C23 0.1022(13) 0.0653(10) 0.0829(12) -0.0023(8) -0.0268(10) -0.0442(9)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.342(2) . ?
N1 C13 1.345(2) . ?
N2 C19 1.374(2) . ?
N2 C22 1.440(2) . ?
N2 C23 1.440(2) . ?
C1 C2 1.428(2) . ?
C1 C6 1.430(2) . ?
C2 C3 1.345(2) . ?
C3 C4 1.409(2) . ?
C4 C5 1.357(2) . ?
C5 C6 1.421(2) . ?
C6 C7 1.407(2) . ?
C7 C8 1.406(2) . ?
C7 C14 1.432(2) . ?
C8 C9 1.421(2) . ?
C8 C13 1.432(2) . ?
C9 C10 1.352(2) . ?
C10 C11 1.411(2) . ?
C11 C12 1.348(2) . ?
C12 C13 1.424(2) . ?
C14 C15 1.197(2) . ?
C15 C16 1.433(2) . ?
C16 C17 1.390(2) . ?
C16 C21 1.391(2) . ?
C17 C18 1.372(2) . ?
C18 C19 1.401(2) . ?
C19 C20 1.404(2) . ?
C20 C21 1.374(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 117.99(11) . . ?
C19 N2 C22 120.94(13) . . ?
C19 N2 C23 120.85(13) . . ?
C22 N2 C23 116.78(13) . . ?
N1 C1 C2 118.47(13) . . ?
N1 C1 C6 123.54(12) . . ?
C2 C1 C6 117.99(13) . . ?
C3 C2 C1 121.11(14) . . ?
C2 C3 C4 120.87(14) . . ?
C5 C4 C3 120.42(15) . . ?
C4 C5 C6 120.74(14) . . ?
C7 C6 C5 123.18(12) . . ?
C7 C6 C1 117.95(12) . . ?
C5 C6 C1 118.87(12) . . ?
C6 C7 C8 119.11(11) . . ?
C6 C7 C14 120.48(12) . . ?
C8 C7 C14 120.41(12) . . ?
C7 C8 C9 123.29(12) . . ?
C7 C8 C13 118.01(12) . . ?
C9 C8 C13 118.70(12) . . ?
C10 C9 C8 120.73(14) . . ?
C9 C10 C11 120.46(14) . . ?
C12 C11 C10 121.07(14) . . ?
C11 C12 C13 120.60(14) . . ?
N1 C13 C12 118.22(12) . . ?
N1 C13 C8 123.36(12) . . ?
C12 C13 C8 118.42(13) . . ?
C15 C14 C7 178.88(14) . . ?
C14 C15 C16 178.54(14) . . ?
C17 C16 C21 117.57(12) . . ?
C17 C16 C15 121.56(12) . . ?
C21 C16 C15 120.87(12) . . ?
C18 C17 C16 121.62(13) . . ?
C17 C18 C19 121.22(12) . . ?
N2 C19 C18 121.41(12) . . ?
N2 C19 C20 121.66(12) . . ?
C18 C19 C20 116.93(12) . . ?
C21 C20 C19 121.30(13) . . ?
C20 C21 C16 121.35(12) . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.027