#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/14/7151483.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151483
loop_
_publ_author_name
'Ihmels, Heiko'
'Faulhaber, Katja'
'Wissel, Kathrin'
'Viola, Giampietro'
'Vedaldi, Daniela'
_publ_section_title
;
 6-Aminoacridizinium bromide: a fluorescence probe which lights up in
 AT-rich regions of DNA
;
_journal_issue                   17
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              2999
_journal_page_last               3001
_journal_paper_doi               10.1039/b305439j
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C13 H13 Cl N2 O'
_chemical_formula_weight         248.70
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                113.6800(10)
_cell_angle_beta                 106.518(2)
_cell_angle_gamma                96.026(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4271(7)
_cell_length_b                   9.2771(9)
_cell_length_c                   9.6627(9)
_cell_measurement_reflns_used    6868
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.068
_cell_measurement_theta_min      2.465
_cell_volume                     566.05(9)
_computing_cell_refinement       'SAINT-NT V5/6.0'
_computing_data_collection       'SMART-NT V5.624'
_computing_data_reduction        'SAINT-NT V5/6.0'
_computing_molecular_graphics    'XP in SHELXL-97'
_computing_publication_material  'XP in SHELXL-97'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex on D8-Goniometer'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10950
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.980000
_exptl_absorpt_correction_T_min  0.792766
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS2.03 (Sheldrick 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.190
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0460
_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/[σ²(Fo²)+(0.0764P)²+0.2539P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                1967
_reflns_number_total             2004
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b305439j.txt
_cod_data_source_block           sadm
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151483
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_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'
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_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_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) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21141463
