# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


data_publication_text
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
#TrackingRef '- cif_complex 1.cif'

_publ_contact_author_name        'Dr. Biplab Mondal'
_publ_contact_author_address     
;Department of Chemistry
Indian Institute of Technology, Guwahati
Guwahati(781039)
Assam - India
;
_publ_contact_author_email       biplab@iitg.ernet.in
loop_
_publ_author_address
;Department of Chemistry
Indian Institute of Technology, Guwahati
Guwahati(781039)
Assam - India
;
_publ_author_name                'Dr. Biplab Mondal'

data_11
_database_code_depnum_ccdc_archive 'CCDC 865490'
#TrackingRef '- cif_complex 1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C13 H17 Cl2 Cu N5 O8'
_chemical_formula_sum            'C13 H17 Cl2 Cu N5 O8'
_exptl_crystal_recrystallization_method 'solvent evapoation'
_chemical_melting_point          ?

_exptl_crystal_description       cube
_exptl_crystal_colour            blue

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         505.77

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   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5238(2)
_cell_length_b                   8.5809(2)
_cell_length_c                   23.5778(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.4430(10)
_cell_angle_gamma                90.00
_cell_volume                     1921.05(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1028
_exptl_absorpt_coefficient_mu    1.469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   SADBAS

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22339
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         28.38
_reflns_number_total             4797
_reflns_number_gt                3964
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. No of restrains used 40.
;

_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^)+(0.0900P)^2^+3.5719P] 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         4797
_refine_ls_number_parameters     271
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1380
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_restrained_S_all      0.986
_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 0.30091(4) 0.81816(5) 0.128745(16) 0.03709(15) Uani 1 1 d . . .
Cl1 Cl 0.54461(9) 0.44771(11) 0.13015(4) 0.0443(2) Uani 1 1 d . . .
N1 N 0.1726(3) 0.6997(3) 0.17621(11) 0.0337(5) Uani 1 1 d . . .
N2 N 0.2286(3) 0.7256(3) 0.05350(12) 0.0362(6) Uani 1 1 d . . .
N3 N 0.4612(3) 0.8730(4) 0.08658(12) 0.0402(6) Uani 1 1 d . . .
C10 C 0.6676(4) 0.9196(5) 0.05236(18) 0.0506(9) Uani 1 1 d . . .
N5 N 0.3448(3) 0.9836(4) 0.18818(13) 0.0455(7) Uani 1 1 d . . .
C9 C 0.4643(3) 0.8006(4) 0.03768(14) 0.0366(7) Uani 1 1 d . . .
N4 N 0.5873(3) 0.8266(4) 0.01541(14) 0.0449(7) Uani 1 1 d . . .
H15 H 0.6117 0.7911 -0.0165 0.054 Uiso 1 1 calc R . .
C6 C 0.0167(3) 0.6205(5) 0.09307(15) 0.0430(8) Uani 1 1 d . . .
H6A H -0.0229 0.7214 0.0824 0.052 Uiso 1 1 calc R . .
H6B H -0.0561 0.5429 0.0849 0.052 Uiso 1 1 calc R . .
C8 C 0.3443(4) 0.7007(4) 0.01564(15) 0.0392(7) Uani 1 1 d . . .
H8A H 0.3138 0.7297 -0.0231 0.047 Uiso 1 1 calc R . .
H8B H 0.3723 0.5920 0.0161 0.047 Uiso 1 1 calc R . .
C1 C 0.2105(4) 0.6950(4) 0.23239(15) 0.0397(7) Uani 1 1 d . . .
H1 H 0.2920 0.7470 0.2460 0.048 Uiso 1 1 calc R . .
C7 C 0.1383(4) 0.5868(4) 0.05672(15) 0.0422(7) Uani 1 1 d . . .
H7A H 0.1936 0.5006 0.0730 0.051 Uiso 1 1 calc R . .
H7B H 0.1016 0.5570 0.0187 0.051 Uiso 1 1 calc R . .
C2 C 0.1344(4) 0.6172(5) 0.27052(16) 0.0465(8) Uani 1 1 d . . .
H2 H 0.1628 0.6177 0.3092 0.056 Uiso 1 1 calc R . .
C4 C -0.0234(4) 0.5384(5) 0.19277(17) 0.0469(8) Uani 1 1 d . . .
H4 H -0.1029 0.4837 0.1786 0.056 Uiso 1 1 calc R . .
C5 C 0.0569(3) 0.6205(4) 0.15592(14) 0.0358(6) Uani 1 1 d . . .
C12 C 0.3422(4) 1.0977(5) 0.21186(16) 0.0450(8) Uani 1 1 d . . .
C3 C 0.0155(4) 0.5384(5) 0.25032(18) 0.0523(9) Uani 1 1 d . . .
H3 H -0.0385 0.4853 0.2753 0.063 Uiso 1 1 calc R . .
C11 C 0.5891(4) 0.9495(5) 0.09654(17) 0.0501(9) Uani 1 1 d . . .
H11 H 0.6161 1.0107 0.1281 0.060 Uiso 1 1 calc R . .
C13 C 0.3318(5) 1.2437(5) 0.2427(2) 0.0623(11) Uani 1 1 d . . .
H13A H 0.2605 1.3080 0.2236 0.093 Uiso 1 1 calc R . .
H13B H 0.4207 1.2969 0.2442 0.093 Uiso 1 1 calc R . .
H13C H 0.3073 1.2224 0.2807 0.093 Uiso 1 1 calc R . .
O1 O 0.4560(4) 0.5488(4) 0.16010(17) 0.0750(10) Uani 1 1 d . . .
O4 O 0.6491(4) 0.5357(5) 0.1044(2) 0.1004(15) Uani 1 1 d . . .
O2 O 0.4606(4) 0.3741(6) 0.08592(18) 0.0939(13) Uani 1 1 d . . .
O3 O 0.6057(6) 0.3353(6) 0.16760(18) 0.1095(17) Uani 1 1 d . . .
O5 O 0.0515(7) 0.9930(5) 0.1073(2) 0.126(2) Uani 1 1 d D . .
O6 O 0.1060(5) 1.2477(5) 0.13053(17) 0.0887(12) Uani 1 1 d D . .
O7 O -0.0680(7) 1.1958(7) 0.0604(4) 0.193(4) Uani 1 1 d D . .
Cl2 Cl 0.06345(9) 1.14441(11) 0.08425(4) 0.0448(2) Uani 1 1 d D . .
O8 O 0.1749(9) 1.1440(15) 0.0486(4) 0.253(7) Uani 1 1 d D . .
H14 H 0.162(5) 0.808(5) 0.039(2) 0.052(12) Uiso 1 1 d . . .
H10 H 0.757(4) 0.948(5) 0.0450(18) 0.045(11) Uiso 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
Cu1 0.0396(2) 0.0410(3) 0.0305(2) -0.00460(15) 0.00179(15) -0.01135(16)
Cl1 0.0424(4) 0.0506(5) 0.0391(4) 0.0023(3) -0.0018(3) 0.0077(3)
N1 0.0318(12) 0.0359(14) 0.0332(13) -0.0025(10) 0.0014(10) -0.0017(10)
N2 0.0380(13) 0.0373(14) 0.0328(13) -0.0031(11) -0.0014(10) -0.0044(11)
N3 0.0408(14) 0.0436(16) 0.0361(14) -0.0003(12) 0.0022(11) -0.0091(12)
C10 0.0405(18) 0.052(2) 0.059(2) 0.0122(18) 0.0010(16) -0.0092(16)
N5 0.0509(16) 0.0455(17) 0.0399(16) -0.0065(13) 0.0031(12) -0.0106(13)
C9 0.0378(15) 0.0367(16) 0.0353(16) 0.0058(13) 0.0031(12) -0.0006(12)
N4 0.0450(15) 0.0462(17) 0.0446(17) 0.0067(13) 0.0116(13) 0.0008(12)
C6 0.0324(15) 0.052(2) 0.0436(18) -0.0034(16) -0.0029(13) -0.0097(14)
C8 0.0424(16) 0.0416(18) 0.0339(16) -0.0038(13) 0.0051(13) -0.0032(13)
C1 0.0370(15) 0.0451(19) 0.0369(17) -0.0015(14) 0.0030(12) -0.0015(13)
C7 0.0445(17) 0.0442(19) 0.0373(17) -0.0086(14) 0.0000(13) -0.0118(14)
C2 0.0515(19) 0.051(2) 0.0379(18) 0.0022(15) 0.0094(14) 0.0032(16)
C4 0.0383(16) 0.050(2) 0.053(2) -0.0038(17) 0.0088(14) -0.0112(15)
C5 0.0302(13) 0.0355(16) 0.0415(17) -0.0044(13) 0.0019(12) -0.0001(12)
C12 0.0464(18) 0.048(2) 0.0408(18) -0.0031(16) 0.0012(14) -0.0077(15)
C3 0.051(2) 0.058(2) 0.050(2) 0.0032(18) 0.0205(17) -0.0078(17)
C11 0.0470(19) 0.056(2) 0.047(2) 0.0011(17) -0.0007(15) -0.0169(17)
C13 0.078(3) 0.045(2) 0.064(3) -0.015(2) 0.006(2) -0.005(2)
O1 0.082(2) 0.067(2) 0.079(2) -0.0074(18) 0.0235(19) 0.0196(17)
O4 0.071(2) 0.088(3) 0.147(4) 0.009(3) 0.043(3) -0.009(2)
O2 0.076(2) 0.123(4) 0.078(3) -0.038(3) -0.019(2) 0.003(2)
O3 0.131(4) 0.130(4) 0.067(2) 0.033(2) 0.003(2) 0.074(3)
O5 0.220(6) 0.047(2) 0.106(4) 0.011(2) -0.029(4) -0.008(3)
O6 0.118(3) 0.061(2) 0.084(3) -0.012(2) -0.008(2) 0.004(2)
O7 0.149(6) 0.113(5) 0.294(10) 0.025(5) -0.131(6) 0.025(4)
Cl2 0.0428(4) 0.0461(5) 0.0456(5) 0.0034(4) 0.0039(3) 0.0029(3)
O8 0.150(6) 0.411(16) 0.217(9) -0.163(10) 0.129(7) -0.116(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
Cu1 N3 1.943(3) . ?
Cu1 N1 1.998(3) . ?
Cu1 N2 2.016(3) . ?
Cu1 N5 2.016(3) . ?
Cl1 O3 1.403(4) . ?
Cl1 O2 1.413(4) . ?
Cl1 O4 1.423(4) . ?
Cl1 O1 1.434(3) . ?
N1 C1 1.346(4) . ?
N1 C5 1.350(4) . ?
N2 C7 1.475(4) . ?
N2 C8 1.486(4) . ?
N3 C9 1.312(4) . ?
N3 C11 1.388(4) . ?
C10 C11 1.353(6) . ?
C10 N4 1.370(5) . ?
N5 C12 1.128(5) . ?
C9 N4 1.339(4) . ?
C9 C8 1.490(5) . ?
C6 C5 1.501(5) . ?
C6 C7 1.521(5) . ?
C1 C2 1.371(5) . ?
C2 C3 1.372(6) . ?
C4 C3 1.379(6) . ?
C4 C5 1.393(5) . ?
C12 C13 1.456(6) . ?
O5 Cl2 1.416(4) . ?
O6 Cl2 1.440(3) . ?
O7 Cl2 1.403(4) . ?
Cl2 O8 1.405(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
N3 Cu1 N1 161.58(12) . . ?
N3 Cu1 N2 82.72(12) . . ?
N1 Cu1 N2 96.34(11) . . ?
N3 Cu1 N5 93.24(12) . . ?
N1 Cu1 N5 94.11(12) . . ?
N2 Cu1 N5 158.08(13) . . ?
O3 Cl1 O2 109.9(3) . . ?
O3 Cl1 O4 111.4(3) . . ?
O2 Cl1 O4 107.2(3) . . ?
O3 Cl1 O1 109.7(3) . . ?
O2 Cl1 O1 108.2(2) . . ?
O4 Cl1 O1 110.3(3) . . ?
C1 N1 C5 118.9(3) . . ?
C1 N1 Cu1 115.9(2) . . ?
C5 N1 Cu1 125.1(2) . . ?
C7 N2 C8 112.2(3) . . ?
C7 N2 Cu1 115.7(2) . . ?
C8 N2 Cu1 111.5(2) . . ?
C9 N3 C11 107.1(3) . . ?
C9 N3 Cu1 114.0(2) . . ?
C11 N3 Cu1 137.9(3) . . ?
C11 C10 N4 106.6(3) . . ?
C12 N5 Cu1 160.7(3) . . ?
N3 C9 N4 110.2(3) . . ?
N3 C9 C8 120.7(3) . . ?
N4 C9 C8 129.0(3) . . ?
C9 N4 C10 108.0(3) . . ?
C5 C6 C7 114.2(3) . . ?
N2 C8 C9 107.0(3) . . ?
N1 C1 C2 123.0(3) . . ?
N2 C7 C6 110.4(3) . . ?
C1 C2 C3 118.4(4) . . ?
C3 C4 C5 119.7(3) . . ?
N1 C5 C4 120.4(3) . . ?
N1 C5 C6 119.3(3) . . ?
C4 C5 C6 120.4(3) . . ?
N5 C12 C13 177.3(4) . . ?
C2 C3 C4 119.6(3) . . ?
C10 C11 N3 108.1(3) . . ?
O7 Cl2 O8 117.0(8) . . ?
O7 Cl2 O5 110.3(4) . . ?
O8 Cl2 O5 108.3(6) . . ?
O7 Cl2 O6 107.4(4) . . ?
O8 Cl2 O6 105.9(4) . . ?
O5 Cl2 O6 107.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.997
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.089