Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2003

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Heiko Ihmels'
'Katja Faulhaber'
'Daniela Vedaldi'
'Giampietro Viola'
'Kathrin Wissel'

_publ_contact_author_name        'Dr Heiko Ihmels'
_publ_contact_author_address     
;
Institute of Organic Chemistry
University of Wurzburg
Am Hubland
Wurzburg
Bavaria
97074
GERMANY
;

_publ_contact_author_email       IHMELS@CHEMIE.UNI-WUERZBURG.DE

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
6-Aminoacridizinium Bromide: A fluorescence probe which
lights up in AT-rich regions of DNA
;

data_sadm
_database_code_CSD               216672

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H13 Cl N2 O'
_chemical_formula_weight         248.70

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   7.4271(7)
_cell_length_b                   9.2771(9)
_cell_length_c                   9.6627(9)
_cell_angle_alpha                113.6800(10)
_cell_angle_beta                 106.518(2)
_cell_angle_gamma                96.026(2)
_cell_volume                     566.05(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6868
_cell_measurement_theta_min      2.465
_cell_measurement_theta_max      25.068

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.792766
_exptl_absorpt_correction_T_max  0.980000
_exptl_absorpt_process_details   'SADABS2.03 (Sheldrick 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex on D8-Goniometer'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10950
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.07
_reflns_number_total             2004
_reflns_number_gt                1967
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART-NT V5.624'
_computing_cell_refinement       'SAINT-NT V5/6.0'
_computing_data_reduction        'SAINT-NT V5/6.0'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXL-97'
_computing_publication_material  'XP in SHELXL-97'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness 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 threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0764P)^2^+0.2539P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2004
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1302
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_restrained_S_all      1.190
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1767(3) 0.3684(2) 0.8602(2) 0.0235(4) Uani 1 1 d . . .
N2 N 0.2966(3) 0.3733(2) 1.0026(2) 0.0276(4) Uani 1 1 d . . .
C3 C 0.3471(3) 0.2318(2) 1.0053(3) 0.0278(5) Uani 1 1 d . . .
H3 H 0.2994 0.1324 0.9082 0.033 Uiso 1 1 calc R . .
C4 C 0.4613(3) 0.2350(3) 1.1425(3) 0.0299(5) Uani 1 1 d . . .
H4 H 0.4926 0.1378 1.1410 0.036 Uiso 1 1 calc R . .
C5 C 0.5360(3) 0.3809(3) 1.2896(3) 0.0302(5) Uani 1 1 d . . .
H5 H 0.6168 0.3820 1.3861 0.036 Uiso 1 1 calc R . .
C6 C 0.4904(3) 0.5183(3) 1.2904(2) 0.0293(5) Uani 1 1 d . . .
H6 H 0.5408 0.6163 1.3888 0.035 Uiso 1 1 calc R . .
C7 C 0.3694(3) 0.5202(2) 1.1485(2) 0.0248(4) Uani 1 1 d . . .
C8 C 0.3185(3) 0.6590(2) 1.1474(2) 0.0271(5) Uani 1 1 d . . .
H8 H 0.3662 0.7576 1.2452 0.033 Uiso 1 1 calc R . .
C9 C 0.2000(3) 0.6578(2) 1.0078(2) 0.0247(4) Uani 1 1 d . . .
C10 C 0.1498(3) 0.8001(2) 1.0032(3) 0.0297(5) Uani 1 1 d . . .
H10 H 0.1959 0.8995 1.1001 0.036 Uiso 1 1 calc R . .
C11 C 0.0385(3) 0.7973(3) 0.8647(3) 0.0303(5) Uani 1 1 d . . .
H11 H 0.0078 0.8941 0.8645 0.036 Uiso 1 1 calc R . .
C12 C -0.0326(3) 0.6497(3) 0.7191(3) 0.0301(5) Uani 1 1 d . . .
H12 H -0.1108 0.6480 0.6214 0.036 Uiso 1 1 calc R . .
C13 C 0.0102(3) 0.5117(3) 0.7188(2) 0.0280(5) Uani 1 1 d . . .
H13 H -0.0394 0.4134 0.6206 0.034 Uiso 1 1 calc R . .
C2 C 0.1274(3) 0.5110(2) 0.8618(2) 0.0192(4) Uani 1 1 d . . .
Cl1 Cl 0.25673(8) 0.90728(6) 0.59981(6) 0.0333(2) Uani 1 1 d . . .
H1 H 0.014(5) 0.217(4) 0.637(4) 0.055(8) Uiso 1 1 d . . .
H2 H 0.147(4) 0.146(4) 0.712(3) 0.047(8) Uiso 1 1 d . . .
H98 H 0.567(6) 0.900(4) 0.609(4) 0.069(10) Uiso 1 1 d . . .
H99 H 0.713(6) 0.961(5) 0.556(5) 0.094(13) Uiso 1 1 d . . .
N1 N 0.1100(3) 0.2310(2) 0.7247(2) 0.0323(4) Uani 1 1 d . . .
O1 O 0.6909(3) 0.8974(2) 0.6087(2) 0.0455(4) Uani 1 1 d . . .

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
C1 0.0242(10) 0.0238(10) 0.0236(10) 0.0100(8) 0.0105(8) 0.0078(8)
N2 0.0296(9) 0.0262(9) 0.0258(9) 0.0097(7) 0.0113(7) 0.0075(7)
C3 0.0327(11) 0.0233(10) 0.0287(11) 0.0112(9) 0.0128(9) 0.0094(8)
C4 0.0315(11) 0.0296(11) 0.0341(12) 0.0173(9) 0.0139(9) 0.0115(9)
C5 0.0294(11) 0.0357(12) 0.0265(11) 0.0155(9) 0.0089(9) 0.0090(9)
C6 0.0287(10) 0.0308(11) 0.0237(10) 0.0093(9) 0.0085(8) 0.0042(8)
C7 0.0246(10) 0.0239(10) 0.0239(10) 0.0075(8) 0.0114(8) 0.0045(8)
C8 0.0317(11) 0.0224(10) 0.0234(10) 0.0060(8) 0.0111(8) 0.0059(8)
C9 0.0265(10) 0.0213(10) 0.0269(10) 0.0084(8) 0.0137(8) 0.0067(8)
C10 0.0346(11) 0.0225(10) 0.0324(11) 0.0096(9) 0.0156(9) 0.0098(8)
C11 0.0333(11) 0.0264(10) 0.0393(12) 0.0177(9) 0.0180(9) 0.0138(9)
C12 0.0301(11) 0.0338(11) 0.0294(11) 0.0171(9) 0.0100(9) 0.0098(9)
C13 0.0294(10) 0.0269(10) 0.0254(10) 0.0104(9) 0.0087(8) 0.0075(8)
C2 0.0212(9) 0.0171(9) 0.0194(9) 0.0066(7) 0.0096(7) 0.0054(7)
Cl1 0.0405(4) 0.0255(3) 0.0264(3) 0.0083(2) 0.0051(2) 0.0128(2)
N1 0.0391(11) 0.0228(9) 0.0244(9) 0.0048(7) 0.0034(8) 0.0128(8)
O1 0.0517(12) 0.0434(10) 0.0430(10) 0.0212(8) 0.0157(8) 0.0144(8)

_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
C1 N1 1.320(3) . ?
C1 N2 1.391(3) . ?
C1 C2 1.404(3) . ?
N2 C3 1.411(3) . ?
N2 C7 1.416(3) . ?
C3 C4 1.342(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.350(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.419(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(3) . ?
C8 C9 1.380(3) . ?
C8 H8 0.9500 . ?
C9 C2 1.416(3) . ?
C9 C10 1.423(3) . ?
C10 C11 1.346(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.418(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.351(3) . ?
C12 H12 0.9500 . ?
C13 C2 1.412(3) . ?
C13 H13 0.9500 . ?
N1 H1 0.89(3) . ?
N1 H2 0.83(3) . ?
O1 H98 0.92(4) . ?
O1 H99 0.95(5) . ?

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
N1 C1 N2 120.26(18) . . ?
N1 C1 C2 120.34(18) . . ?
N2 C1 C2 119.40(18) . . ?
C1 N2 C3 120.74(17) . . ?
C1 N2 C7 120.69(17) . . ?
C3 N2 C7 118.57(18) . . ?
C4 C3 N2 121.14(19) . . ?
C4 C3 H3 119.4 . . ?
N2 C3 H3 119.4 . . ?
C3 C4 C5 121.16(19) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 118.93(19) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 121.8(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 N2 118.94(19) . . ?
C8 C7 C6 122.69(19) . . ?
N2 C7 C6 118.37(18) . . ?
C9 C8 C7 121.63(19) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C2 119.48(18) . . ?
C8 C9 C10 122.53(19) . . ?
C2 C9 C10 117.97(19) . . ?
C11 C10 C9 121.6(2) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 119.93(19) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C2 121.08(19) . . ?
C12 C13 H13 119.5 . . ?
C2 C13 H13 119.5 . . ?
C1 C2 C13 120.99(17) . . ?
C1 C2 C9 119.86(18) . . ?
C13 C2 C9 119.13(18) . . ?
C1 N1 H1 123(2) . . ?
C1 N1 H2 125(2) . . ?
H1 N1 H2 112(3) . . ?
H98 O1 H99 104(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 N2 C3 -0.7(3) . . . . ?
C2 C1 N2 C3 179.36(17) . . . . ?
N1 C1 N2 C7 179.81(18) . . . . ?
C2 C1 N2 C7 -0.1(3) . . . . ?
C1 N2 C3 C4 -179.37(18) . . . . ?
C7 N2 C3 C4 0.1(3) . . . . ?
N2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C1 N2 C7 C8 0.3(3) . . . . ?
C3 N2 C7 C8 -179.12(17) . . . . ?
C1 N2 C7 C6 179.71(17) . . . . ?
C3 N2 C7 C6 0.3(3) . . . . ?
C5 C6 C7 C8 178.90(19) . . . . ?
C5 C6 C7 N2 -0.5(3) . . . . ?
N2 C7 C8 C9 -0.5(3) . . . . ?
C6 C7 C8 C9 -179.81(18) . . . . ?
C7 C8 C9 C2 0.3(3) . . . . ?
C7 C8 C9 C10 -178.36(18) . . . . ?
C8 C9 C10 C11 178.04(19) . . . . ?
C2 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C2 -0.6(3) . . . . ?
N1 C1 C2 C13 -1.6(3) . . . . ?
N2 C1 C2 C13 178.33(17) . . . . ?
N1 C1 C2 C9 -179.95(18) . . . . ?
N2 C1 C2 C9 -0.1(3) . . . . ?
C12 C13 C2 C1 -178.04(18) . . . . ?
C12 C13 C2 C9 0.4(3) . . . . ?
C8 C9 C2 C1 -0.1(3) . . . . ?
C10 C9 C2 C1 178.68(17) . . . . ?
C8 C9 C2 C13 -178.48(17) . . . . ?
C10 C9 C2 C13 0.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.076