# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Zong-Wan Mao'
_publ_contact_author_email       CESMZW@MAIL.SYSU.EDU.CN

_publ_section_title              
;
Double-strand DNA cleavage by copper complexes of
2,2'-dipyridyl with guanidinium/ammonium pendants
;
loop_
_publ_author_name
'Zong-Wan Mao.'
'Juan He.'
'Ping Hu.'
'Liang-Nian Ji.'
'Hongzhe Sun.'
;
Ming-Liang Tong
;
'Yu Wang.'

# Attachment 'B801549J R1_CIF for Complex 1.cif'

data_complex_1
_database_code_depnum_ccdc_archive 'CCDC 632380'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 Cl4 Cu N8 O8'
_chemical_formula_weight         633.72

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'
O O 0.0106 0.0060 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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'

_cell_length_a                   17.202(3)
_cell_length_b                   8.9681(13)
_cell_length_c                   15.145(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.609(3)
_cell_angle_gamma                90.00
_cell_volume                     2334.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      -3
_cell_measurement_theta_max      52

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1284
_exptl_absorpt_coefficient_mu    1.454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      293(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_type  ccd
_diffrn_measurement_method       phi
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            4360
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2419
_reflns_number_gt                1973
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0750P)^2^+3.4879P] 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         2419
_refine_ls_number_parameters     179
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1380
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.072
_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
Cu1 Cu 0.5000 0.03938(6) 0.7500 0.0418(2) Uani 1 2 d S . .
Cl1 Cl 0.55020(6) -0.13386(10) 0.66180(8) 0.0533(3) Uani 1 1 d . . .
N1 N 0.47104(18) 0.2115(3) 0.8284(2) 0.0390(7) Uani 1 1 d . . .
N2 N 0.3185(2) 0.3822(4) 1.0614(2) 0.0535(9) Uani 1 1 d D . .
H2 H 0.308(4) 0.438(6) 1.013(2) 0.10(2) Uiso 1 1 d D . .
N3 N 0.3159(3) 0.3024(6) 1.2045(3) 0.0778(13) Uani 1 1 d D . .
H3A H 0.3550(19) 0.238(4) 1.197(3) 0.069(15) Uiso 1 1 d D . .
H3B H 0.302(4) 0.313(7) 1.2606(14) 0.10(2) Uiso 1 1 d D . .
N4 N 0.2266(3) 0.4701(5) 1.1527(3) 0.0709(12) Uani 1 1 d D . .
H4A H 0.212(3) 0.541(3) 1.113(2) 0.052(13) Uiso 1 1 d D . .
H4B H 0.197(3) 0.463(7) 1.200(3) 0.10(2) Uiso 1 1 d D . .
C1 C 0.4408(2) 0.2023(4) 0.9078(3) 0.0457(9) Uani 1 1 d . . .
H1 H 0.4351 0.1084 0.9327 0.055 Uiso 1 1 calc R . .
C2 C 0.4176(2) 0.3257(4) 0.9549(3) 0.0465(9) Uani 1 1 d . . .
C3 C 0.4258(3) 0.4642(4) 0.9167(3) 0.0541(11) Uani 1 1 d . . .
H3 H 0.4101 0.5496 0.9459 0.065 Uiso 1 1 calc R . .
C4 C 0.4574(3) 0.4744(4) 0.8346(3) 0.0520(10) Uani 1 1 d . . .
H4 H 0.4624 0.5668 0.8076 0.062 Uiso 1 1 calc R . .
C5 C 0.4814(2) 0.3470(4) 0.7931(3) 0.0394(8) Uani 1 1 d . . .
C6 C 0.3892(3) 0.3020(5) 1.0461(3) 0.0570(11) Uani 1 1 d . . .
H6 H 0.3803 0.1964 1.0550 0.068 Uiso 1 1 calc R . .
H6B H 0.4293 0.3337 1.0892 0.068 Uiso 1 1 calc R . .
C7 C 0.2873(3) 0.3844(5) 1.1398(3) 0.0503(10) Uani 1 1 d . . .
Cl2 Cl 0.67943(6) 0.13922(12) 0.89840(6) 0.0503(3) Uani 1 1 d . . .
O1 O 0.6440(2) 0.0646(4) 0.8232(2) 0.0710(10) Uani 1 1 d U . .
O2 O 0.6734(4) 0.0488(6) 0.9727(3) 0.135(2) Uani 1 1 d U . .
O3 O 0.7604(2) 0.1605(6) 0.8868(3) 0.1102(16) Uani 1 1 d U . .
O4 O 0.6435(3) 0.2746(5) 0.9141(4) 0.1197(18) Uani 1 1 d U . .

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
Cu1 0.0434(4) 0.0205(3) 0.0618(5) 0.000 0.0064(3) 0.000
Cl1 0.0575(6) 0.0259(5) 0.0768(7) -0.0092(4) 0.0065(5) 0.0017(4)
N1 0.0396(17) 0.0234(14) 0.0543(19) 0.0003(13) 0.0055(14) 0.0010(12)
N2 0.054(2) 0.058(2) 0.049(2) 0.0003(18) 0.0065(17) 0.0132(17)
N3 0.092(3) 0.085(3) 0.058(3) 0.016(2) 0.014(2) 0.030(3)
N4 0.066(3) 0.084(3) 0.065(3) 0.015(2) 0.022(2) 0.025(2)
C1 0.042(2) 0.0320(19) 0.063(2) 0.0005(18) 0.0052(18) 0.0016(16)
C2 0.042(2) 0.041(2) 0.057(2) -0.0031(18) 0.0036(18) 0.0056(17)
C3 0.061(3) 0.036(2) 0.065(3) -0.0080(19) 0.004(2) 0.0089(19)
C4 0.067(3) 0.0259(19) 0.063(3) -0.0017(18) 0.004(2) 0.0028(18)
C5 0.040(2) 0.0251(16) 0.052(2) -0.0010(15) -0.0009(16) -0.0011(15)
C6 0.057(3) 0.054(3) 0.061(3) 0.003(2) 0.009(2) 0.015(2)
C7 0.055(3) 0.044(2) 0.052(2) 0.0006(19) 0.0053(19) -0.0001(19)
Cl2 0.0540(6) 0.0555(6) 0.0413(5) 0.0009(4) 0.0004(4) -0.0073(5)
O1 0.0598(19) 0.097(3) 0.0557(18) -0.0196(18) -0.0041(15) 0.0073(18)
O2 0.195(5) 0.141(4) 0.066(3) 0.034(3) -0.012(3) -0.060(4)
O3 0.059(2) 0.171(5) 0.099(3) -0.032(3) -0.002(2) -0.010(3)
O4 0.105(3) 0.084(3) 0.167(4) -0.041(3) -0.030(3) 0.016(3)

_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
Cu1 N1 2.024(3) . ?
Cu1 N1 2.024(3) 2_656 ?
Cu1 Cl1 2.2469(11) 2_656 ?
Cu1 Cl1 2.2469(11) . ?
Cu1 O1 2.677(3) . ?
N1 C1 1.334(5) . ?
N1 C5 1.342(4) . ?
N2 C7 1.324(5) . ?
N2 C6 1.440(5) . ?
N2 H2 0.9000(11) . ?
N3 C7 1.304(6) . ?
N3 H3A 0.8999(11) . ?
N3 H3B 0.8999(11) . ?
N4 C7 1.319(6) . ?
N4 H4A 0.9000(11) . ?
N4 H4B 0.9000(11) . ?
C1 C2 1.385(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(6) . ?
C2 C6 1.501(6) . ?
C3 C4 1.383(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C5 1.480(8) 2_656 ?
C6 H6 0.9700 . ?
C6 H6B 0.9700 . ?
Cl2 O4 1.387(5) . ?
Cl2 O2 1.395(4) . ?
Cl2 O3 1.425(4) . ?
Cl2 O1 1.433(3) . ?

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 Cu1 N1 80.56(17) . 2_656 ?
N1 Cu1 Cl1 93.85(9) . 2_656 ?
N1 Cu1 Cl1 171.05(9) 2_656 2_656 ?
N1 Cu1 Cl1 171.05(9) . . ?
N1 Cu1 Cl1 93.85(9) 2_656 . ?
Cl1 Cu1 Cl1 92.51(6) 2_656 . ?
N1 Cu1 O1 86.59(11) . . ?
N1 Cu1 O1 86.01(12) 2_656 . ?
Cl1 Cu1 O1 100.71(9) 2_656 . ?
Cl1 Cu1 O1 86.05(8) . . ?
C1 N1 C5 118.6(3) . . ?
C1 N1 Cu1 126.7(2) . . ?
C5 N1 Cu1 114.6(3) . . ?
C7 N2 C6 122.1(4) . . ?
C7 N2 H2 131(4) . . ?
C6 N2 H2 106(4) . . ?
C7 N3 H3A 122(3) . . ?
C7 N3 H3B 123(4) . . ?
H3A N3 H3B 115(5) . . ?
C7 N4 H4A 121(3) . . ?
C7 N4 H4B 124(4) . . ?
H4A N4 H4B 115(5) . . ?
N1 C1 C2 123.2(4) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C3 C2 C1 117.8(4) . . ?
C3 C2 C6 123.8(4) . . ?
C1 C2 C6 118.4(4) . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 121.4(4) . . ?
N1 C5 C5 115.0(2) . 2_656 ?
C4 C5 C5 123.6(2) . 2_656 ?
N2 C6 C2 113.0(4) . . ?
N2 C6 H6 109.0 . . ?
C2 C6 H6 109.0 . . ?
N2 C6 H6B 109.0 . . ?
C2 C6 H6B 109.0 . . ?
H6 C6 H6B 107.8 . . ?
N3 C7 N4 119.4(4) . . ?
N3 C7 N2 120.7(4) . . ?
N4 C7 N2 119.9(4) . . ?
O4 Cl2 O2 108.7(4) . . ?
O4 Cl2 O3 110.5(3) . . ?
O2 Cl2 O3 106.6(4) . . ?
O4 Cl2 O1 111.6(3) . . ?
O2 Cl2 O1 109.0(3) . . ?
O3 Cl2 O1 110.3(2) . . ?
Cl2 O1 Cu1 136.1(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.9000(11) 2.57(5) 3.157(8) 123(5) 3_455
N3 H3A Cl1 0.8999(11) 2.79(4) 3.357(5) 122(4) 5_657
N3 H3B O3 0.8999(11) 2.082(8) 2.980(7) 176(6) 8_456
N4 H4A O2 0.9000(11) 2.20(3) 2.923(6) 137(4) 3_455
N4 H4B O1 0.9000(11) 2.127(12) 3.018(5) 170(6) 8_456

_diffrn_measured_fraction_theta_max 0.945
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.945
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.084