#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/02/7000255.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_7000255
loop_
_publ_author_name
'Chen, Zhen-Feng'
'Liu, Yan-Cheng'
'Liu, Li-Min'
'Wang, Heng-Shan'
'Qin, San-Hai'
'Wang, Bo-Long'
'Bian, He-Dong'
'Yang, Bin'
'Fun, Hoong-Kun'
'Liu, Hua-Gang'
'Liang, Hong'
'Orvig, Chris'
_publ_section_title
;
 Potential new inorganic antitumour agents from combining the
 anticancer traditional Chinese medicine (TCM) liriodenine with metal
 ions, and DNA binding studies
;
_journal_issue                   2
_journal_name_full               'Dalton Transactions'
_journal_page_first              262
_journal_page_last               272
_journal_paper_doi               10.1039/b813363h
_journal_year                    2009
_chemical_formula_moiety         'C19 H9 N O3, 2(H Cl3)'
_chemical_formula_sum            'C19 H11 Cl6 N O3'
_chemical_formula_weight         513.99
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.135(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.529(5)
_cell_length_b                   12.4079(18)
_cell_length_c                   13.862(2)
_cell_measurement_reflns_used    6637
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      3.0
_cell_volume                     4164.1(12)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20281
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.847
_exptl_absorpt_correction_T_max  0.8488
_exptl_absorpt_correction_T_min  0.7017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.864
_refine_diff_density_min         -1.041
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3817
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0843
_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)+(0.0878P)²+18.8362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2064
_refine_ls_wR_factor_ref         0.2167
_reflns_number_gt                3162
_reflns_number_total             3817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b813363h.txt
_cod_data_source_block           shelxl
_cod_original_cell_volume        4164.2(12)
_cod_original_sg_symbol_Hall     '-c 2yc'
_cod_original_sg_symbol_H-M      'c 2/c'
_cod_database_code               7000255
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Cl1 Cl 0.27076(9) 0.80592(15) 0.21479(15) 0.0836(6) Uani 1 1 d . . .
Cl2 Cl 0.21856(6) 0.75490(15) 0.35597(13) 0.0702(5) Uani 1 1 d . . .
Cl3 Cl 0.25879(7) 0.58484(13) 0.26622(14) 0.0670(5) Uani 1 1 d . . .
Cl4A Cl 0.4556(3) 1.0427(5) 0.6597(6) 0.0600(16) Uiso 0.25 1 d PD . .
Cl4B Cl 0.45085(18) 1.0528(3) 0.6084(5) 0.0775(11) Uiso 0.50 1 d P . .
Cl4C Cl 0.4406(3) 1.0472(5) 0.5558(7) 0.0638(17) Uiso 0.25 1 d PD . .
Cl5A Cl 0.3741(5) 1.0109(9) 0.4491(7) 0.092(3) Uiso 0.25 1 d PD . .
Cl5B Cl 0.3333(3) 0.9742(5) 0.4593(5) 0.1190(19) Uiso 0.50 1 d PD . .
Cl5C Cl 0.3533(4) 0.9809(6) 0.4414(5) 0.0614(16) Uiso 0.25 1 d PD . .
Cl6A Cl 0.3429(4) 1.0021(7) 0.6184(8) 0.078(2) Uiso 0.25 1 d PD . .
Cl6B Cl 0.3613(2) 0.9984(4) 0.6644(5) 0.0690(12) Uiso 0.50 1 d P . .
Cl6C Cl 0.3802(4) 1.0040(8) 0.6908(8) 0.079(3) Uiso 0.25 1 d P . .
O1 O 0.36966(14) 0.7177(3) 0.5550(3) 0.0461(8) Uani 1 1 d . . .
O2 O 0.60965(14) 0.3350(3) 0.6626(3) 0.0510(9) Uani 1 1 d . . .
O3 O 0.52009(14) 0.2882(3) 0.6302(3) 0.0478(9) Uani 1 1 d . . .
N1 N 0.47654(17) 0.7716(3) 0.6121(3) 0.0425(9) Uani 1 1 d . . .
C1 C 0.40330(18) 0.6443(4) 0.5772(3) 0.0350(10) Uani 1 1 d . . .
C2 C 0.46325(18) 0.6680(4) 0.6069(3) 0.0352(10) Uani 1 1 d . . .
C3 C 0.50102(18) 0.5820(4) 0.6244(3) 0.0318(9) Uani 1 1 d . . .
C4 C 0.48320(17) 0.4720(4) 0.6171(3) 0.0310(9) Uani 1 1 d . . .
C5 C 0.42549(18) 0.4464(4) 0.5924(3) 0.0343(10) Uani 1 1 d . . .
C6 C 0.38706(18) 0.5307(4) 0.5735(3) 0.0329(9) Uani 1 1 d . . .
C7 C 0.5294(2) 0.7958(4) 0.6365(4) 0.0483(12) Uani 1 1 d . . .
H7 H 0.5396 0.8697 0.6423 0.058 Uiso 1 1 calc R . .
C8 C 0.5698(2) 0.7198(4) 0.6536(4) 0.0456(12) Uani 1 1 d . . .
H8 H 0.6066 0.7419 0.6695 0.055 Uiso 1 1 calc R . .
C9 C 0.55705(18) 0.6106(4) 0.6477(3) 0.0361(10) Uani 1 1 d . . .
C10 C 0.59724(18) 0.5289(4) 0.6632(3) 0.0383(11) Uani 1 1 d . . .
H10 H 0.6347 0.5456 0.6789 0.046 Uiso 1 1 calc R . .
C11 C 0.57910(19) 0.4263(4) 0.6546(3) 0.0386(11) Uani 1 1 d . . .
C12 C 0.52470(19) 0.3974(4) 0.6343(3) 0.0357(10) Uani 1 1 d . . .
C13 C 0.5742(2) 0.2464(4) 0.6550(4) 0.0498(13) Uani 1 1 d . . .
H13A H 0.5876 0.2067 0.7228 0.060 Uiso 1 1 calc R . .
H13B H 0.5734 0.1962 0.5989 0.060 Uiso 1 1 calc R . .
C14 C 0.3315(2) 0.5071(4) 0.5502(4) 0.0413(11) Uani 1 1 d . . .
H14 H 0.3059 0.5644 0.5382 0.050 Uiso 1 1 calc R . .
C15 C 0.3138(2) 0.4023(5) 0.5444(4) 0.0488(12) Uani 1 1 d . . .
H15 H 0.2761 0.3869 0.5283 0.059 Uiso 1 1 calc R . .
C16 C 0.3515(2) 0.3193(5) 0.5624(4) 0.0506(13) Uani 1 1 d . . .
H16 H 0.3395 0.2467 0.5587 0.061 Uiso 1 1 calc R . .
C17 C 0.4059(2) 0.3404(4) 0.5854(4) 0.0426(11) Uani 1 1 d . . .
H17 H 0.4309 0.2820 0.5967 0.051 Uiso 1 1 calc R . .
C18 C 0.2694(2) 0.7174(4) 0.3124(4) 0.0447(12) Uani 1 1 d . . .
H18 H 0.3061 0.7211 0.3740 0.054 Uiso 1 1 calc R . .
C19 C 0.3945(2) 0.9690(5) 0.5798(5) 0.0602(15) Uani 1 1 d D . .
H13 H 0.404(2) 0.898(4) 0.586(4) 0.040(13) Uiso 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'
Cl Cl 0.1484 0.1585 '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'
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
C11 O2 C13 106.3(4) . . ?
C12 O3 C13 106.7(4) . . ?
C2 N1 C7 117.4(4) . . ?
O1 C1 C6 122.1(4) . . ?
O1 C1 C2 120.4(4) . . ?
C6 C1 C2 117.4(4) . . ?
N1 C2 C3 124.6(4) . . ?
N1 C2 C1 115.6(4) . . ?
C3 C2 C1 119.8(4) . . ?
C2 C3 C9 116.7(4) . . ?
C2 C3 C4 121.0(4) . . ?
C9 C3 C4 122.3(4) . . ?
C12 C4 C3 114.1(4) . . ?
C12 C4 C5 125.4(4) . . ?
C3 C4 C5 120.5(4) . . ?
C17 C5 C6 117.7(4) . . ?
C17 C5 C4 122.9(4) . . ?
C6 C5 C4 119.5(4) . . ?
C14 C6 C5 120.0(4) . . ?
C14 C6 C1 118.2(4) . . ?
C5 C6 C1 121.8(4) . . ?
N1 C7 C8 123.6(5) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 120.3(5) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 122.4(4) . . ?
C8 C9 C3 117.4(4) . . ?
C10 C9 C3 120.2(4) . . ?
C11 C10 C9 116.2(4) . . ?
C11 C10 H10 121.9 . . ?
C9 C10 H10 121.9 . . ?
C10 C11 O2 126.5(4) . . ?
C10 C11 C12 124.1(4) . . ?
O2 C11 C12 109.4(4) . . ?
O3 C12 C4 127.5(4) . . ?
O3 C12 C11 109.3(4) . . ?
C4 C12 C11 123.1(4) . . ?
O2 C13 O3 107.8(4) . . ?
O2 C13 H13A 110.1 . . ?
O3 C13 H13A 110.1 . . ?
O2 C13 H13B 110.1 . . ?
O3 C13 H13B 110.1 . . ?
H13A C13 H13B 108.5 . . ?
C15 C14 C6 120.9(5) . . ?
C15 C14 H14 119.6 . . ?
C6 C14 H14 119.6 . . ?
C14 C15 C16 119.2(5) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 121.0(5) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C5 121.3(5) . . ?
C16 C17 H17 119.4 . . ?
C5 C17 H17 119.4 . . ?
Cl3 C18 Cl2 110.2(3) . . ?
Cl3 C18 Cl1 111.0(3) . . ?
Cl2 C18 Cl1 111.2(3) . . ?
Cl3 C18 H18 108.1 . . ?
Cl2 C18 H18 108.1 . . ?
Cl1 C18 H18 108.1 . . ?
Cl4C C19 Cl6A 131.0(5) . . ?
Cl4C C19 Cl4B 22.6(2) . . ?
Cl6A C19 Cl4B 120.7(5) . . ?
Cl4C C19 Cl5A 64.5(5) . . ?
Cl6A C19 Cl5A 107.7(6) . . ?
Cl4B C19 Cl5A 86.1(5) . . ?
Cl4C C19 Cl6B 127.3(5) . . ?
Cl6A C19 Cl6B 20.7(3) . . ?
Cl4B C19 Cl6B 110.0(4) . . ?
Cl5A C19 Cl6B 126.8(5) . . ?
Cl4C C19 Cl6C 117.1(5) . . ?
Cl6A C19 Cl6C 36.1(5) . . ?
Cl4B C19 Cl6C 97.2(5) . . ?
Cl5A C19 Cl6C 137.6(6) . . ?
Cl6B C19 Cl6C 15.8(3) . . ?
Cl4C C19 Cl5C 85.2(5) . . ?
Cl6A C19 Cl5C 95.7(5) . . ?
Cl4B C19 Cl5C 106.8(5) . . ?
Cl5A C19 Cl5C 20.8(3) . . ?
Cl6B C19 Cl5C 116.3(5) . . ?
Cl6C C19 Cl5C 130.9(5) . . ?
Cl4C C19 Cl5B 104.3(5) . . ?
Cl6A C19 Cl5B 75.3(5) . . ?
Cl4B C19 Cl5B 124.2(5) . . ?
Cl5A C19 Cl5B 40.8(4) . . ?
Cl6B C19 Cl5B 95.9(4) . . ?
Cl6C C19 Cl5B 111.3(5) . . ?
Cl5C C19 Cl5B 21.8(3) . . ?
Cl4C C19 Cl4A 44.7(4) . . ?
Cl6A C19 Cl4A 108.7(5) . . ?
Cl4B C19 Cl4A 22.2(2) . . ?
Cl5A C19 Cl4A 108.0(6) . . ?
Cl6B C19 Cl4A 93.1(4) . . ?
Cl6C C19 Cl4A 78.5(5) . . ?
Cl5C C19 Cl4A 128.6(5) . . ?
Cl5B C19 Cl4A 143.4(5) . . ?
Cl4C C19 H13 113(3) . . ?
Cl6A C19 H13 115(3) . . ?
Cl4B C19 H13 113(3) . . ?
Cl5A C19 H13 110(3) . . ?
Cl6B C19 H13 109(3) . . ?
Cl6C C19 H13 107(3) . . ?
Cl5C C19 H13 102(3) . . ?
Cl5B C19 H13 103(3) . . ?
Cl4A C19 H13 107(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
Cl1 C18 1.754(5) . ?
Cl2 C18 1.751(5) . ?
Cl3 C18 1.745(5) . ?
Cl4A C19 1.795(8) . ?
Cl4B C19 1.728(7) . ?
Cl4C C19 1.696(8) . ?
Cl5A C19 1.745(10) . ?
Cl5B C19 1.793(8) . ?
Cl5C C19 1.784(9) . ?
Cl6A C19 1.713(9) . ?
Cl6B C19 1.769(8) . ?
Cl6C C19 1.783(11) . ?
O1 C1 1.223(5) . ?
O2 C11 1.371(6) . ?
O2 C13 1.422(7) . ?
O3 C12 1.359(6) . ?
O3 C13 1.429(6) . ?
N1 C2 1.327(6) . ?
N1 C7 1.336(7) . ?
C1 C6 1.469(6) . ?
C1 C2 1.500(6) . ?
C2 C3 1.415(6) . ?
C3 C9 1.431(6) . ?
C3 C4 1.434(6) . ?
C4 C12 1.382(6) . ?
C4 C5 1.461(6) . ?
C5 C17 1.403(7) . ?
C5 C6 1.408(6) . ?
C6 C14 1.404(6) . ?
C7 C8 1.373(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.422(6) . ?
C10 C11 1.349(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.400(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.375(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.371(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18 1.0000 . ?
C19 H13 0.91(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
C7 N1 C2 C3 -0.6(7) . . . . ?
C7 N1 C2 C1 -178.8(4) . . . . ?
O1 C1 C2 N1 3.2(6) . . . . ?
C6 C1 C2 N1 -178.3(4) . . . . ?
O1 C1 C2 C3 -175.2(4) . . . . ?
C6 C1 C2 C3 3.4(6) . . . . ?
N1 C2 C3 C9 -1.0(6) . . . . ?
C1 C2 C3 C9 177.2(4) . . . . ?
N1 C2 C3 C4 -180.0(4) . . . . ?
C1 C2 C3 C4 -1.8(6) . . . . ?
C2 C3 C4 C12 178.9(4) . . . . ?
C9 C3 C4 C12 -0.1(5) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C9 C3 C4 C5 -179.6(4) . . . . ?
C12 C4 C5 C17 1.2(6) . . . . ?
C3 C4 C5 C17 -179.4(4) . . . . ?
C12 C4 C5 C6 -178.0(4) . . . . ?
C3 C4 C5 C6 1.4(6) . . . . ?
C17 C5 C6 C14 1.0(6) . . . . ?
C4 C5 C6 C14 -179.7(4) . . . . ?
C17 C5 C6 C1 -178.9(4) . . . . ?
C4 C5 C6 C1 0.4(6) . . . . ?
O1 C1 C6 C14 -4.1(6) . . . . ?
C2 C1 C6 C14 177.4(4) . . . . ?
O1 C1 C6 C5 175.8(4) . . . . ?
C2 C1 C6 C5 -2.7(6) . . . . ?
C2 N1 C7 C8 1.6(8) . . . . ?
N1 C7 C8 C9 -1.0(8) . . . . ?
C7 C8 C9 C10 179.1(4) . . . . ?
C7 C8 C9 C3 -0.6(7) . . . . ?
C2 C3 C9 C8 1.5(6) . . . . ?
C4 C3 C9 C8 -179.5(4) . . . . ?
C2 C3 C9 C10 -178.2(4) . . . . ?
C4 C3 C9 C10 0.8(6) . . . . ?
C8 C9 C10 C11 -179.6(4) . . . . ?
C3 C9 C10 C11 0.1(6) . . . . ?
C9 C10 C11 O2 177.6(4) . . . . ?
C9 C10 C11 C12 -1.7(6) . . . . ?
C13 O2 C11 C10 176.3(5) . . . . ?
C13 O2 C11 C12 -4.3(5) . . . . ?
C13 O3 C12 C4 -179.3(4) . . . . ?
C13 O3 C12 C11 3.6(5) . . . . ?
C3 C4 C12 O3 -178.3(4) . . . . ?
C5 C4 C12 O3 1.2(7) . . . . ?
C3 C4 C12 C11 -1.5(6) . . . . ?
C5 C4 C12 C11 178.0(4) . . . . ?
C10 C11 C12 O3 179.9(4) . . . . ?
O2 C11 C12 O3 0.5(5) . . . . ?
C10 C11 C12 C4 2.6(7) . . . . ?
O2 C11 C12 C4 -176.8(4) . . . . ?
C11 O2 C13 O3 6.5(5) . . . . ?
C12 O3 C13 O2 -6.2(5) . . . . ?
C5 C6 C14 C15 -0.7(7) . . . . ?
C1 C6 C14 C15 179.2(4) . . . . ?
C6 C14 C15 C16 0.3(7) . . . . ?
C14 C15 C16 C17 -0.2(8) . . . . ?
C15 C16 C17 C5 0.6(8) . . . . ?
C6 C5 C17 C16 -1.0(7) . . . . ?
C4 C5 C17 C16 179.8(4) . . . . ?
