# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sdsd_0m
_database_code_depnum_ccdc_archive 'CCDC 1038199'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H32 Cl4 Cu2 N4 O2'
_chemical_formula_sum            'C22 H32 Cl4 Cu2 N4 O2'
_chemical_formula_weight         653.42

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'

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                   9.1653(5)
_cell_length_b                   7.2194(4)
_cell_length_c                   20.4311(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.455(2)
_cell_angle_gamma                90.00
_cell_volume                     1349.43(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    20059
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.6

_exptl_crystal_description       columner
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             668
_exptl_absorpt_coefficient_mu    1.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3706
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20059
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         28.57
_reflns_number_total             3444
_reflns_number_gt                2927
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond 3.0'
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1200P)²+0.4335P] where P=(Fo²+2Fc²)/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         3444
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1584
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 0.43468(4) 0.74171(4) 0.488996(16) 0.03956(17) Uani 1 1 d . . .
Cl2 Cl 0.57529(7) 0.61017(10) 0.57182(3) 0.0441(2) Uani 1 1 d . . .
Cl1 Cl 0.62835(8) 0.87660(11) 0.44367(4) 0.0509(2) Uani 1 1 d . . .
N2 N 0.2454(3) 0.6880(3) 0.53260(11) 0.0389(5) Uani 1 1 d . . .
N1 N 0.2873(3) 0.8439(3) 0.41922(11) 0.0444(6) Uani 1 1 d . . .
C7 C 0.1261(4) 0.7515(4) 0.49785(18) 0.0439(7) Uani 1 1 d . . .
C8 C -0.0130(4) 0.7401(4) 0.5204(2) 0.0575(10) Uani 1 1 d . . .
H8 H -0.0932 0.7853 0.4953 0.069 Uiso 1 1 calc R . .
C11 C 0.2265(3) 0.6082(5) 0.58955(16) 0.0504(7) Uani 1 1 d . . .
H11 H 0.3075 0.5595 0.6132 0.060 Uiso 1 1 calc R . .
C9 C -0.0304(4) 0.6607(5) 0.5806(2) 0.0611(9) Uani 1 1 d . . .
H9 H -0.1225 0.6525 0.5972 0.073 Uiso 1 1 calc R . .
C10 C 0.0902(4) 0.5940(5) 0.61573(19) 0.0621(9) Uani 1 1 d . . .
H10 H 0.0812 0.5399 0.6566 0.074 Uiso 1 1 calc R . .
C6 C 0.1572(4) 0.8343(4) 0.43492(15) 0.0490(7) Uani 1 1 d . . .
H6 H 0.0816 0.8792 0.4069 0.059 Uiso 1 1 calc R . .
C5 C 0.3189(5) 0.9273(5) 0.35604(16) 0.0630(9) Uani 1 1 d . . .
H5B H 0.3979 1.0160 0.3628 0.076 Uiso 1 1 calc R . .
H5A H 0.2332 0.9936 0.3384 0.076 Uiso 1 1 calc R . .
C4 C 0.3605(5) 0.7856(6) 0.30803(19) 0.0638(9) Uani 1 1 d . . .
H4A H 0.4414 0.7138 0.3275 0.077 Uiso 1 1 calc R . .
H4B H 0.3948 0.8482 0.2699 0.077 Uiso 1 1 calc R . .
C3 C 0.2384(5) 0.6534(7) 0.28562(18) 0.0732(11) Uani 1 1 d . . .
H3A H 0.1922 0.6041 0.3234 0.088 Uiso 1 1 calc R . .
H3B H 0.1649 0.7189 0.2584 0.088 Uiso 1 1 calc R . .
C2 C 0.3016(6) 0.4967(8) 0.2470(2) 0.0922(16) Uani 1 1 d . . .
H2A H 0.3503 0.5489 0.2104 0.111 Uiso 1 1 calc R . .
H2B H 0.3749 0.4333 0.2749 0.111 Uiso 1 1 calc R . .
C1 C 0.1969(10) 0.3642(11) 0.2223(3) 0.136(3) Uani 1 1 d D . .
H1A H 0.2415 0.2437 0.2301 0.163 Uiso 1 1 calc R . .
H1B H 0.1159 0.3713 0.2507 0.163 Uiso 1 1 calc R . .
O1 O 0.1429(6) 0.3603(16) 0.1667(2) 0.236(5) Uani 1 1 d D . .
H1 H 0.1993 0.4076 0.1419 0.354 Uiso 1 1 calc R . .

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 0.0312(3) 0.0466(3) 0.0404(3) 0.00401(12) -0.00190(16) -0.00221(12)
Cl2 0.0355(4) 0.0480(4) 0.0476(4) 0.0009(3) -0.0072(3) 0.0026(3)
Cl1 0.0441(4) 0.0574(5) 0.0518(4) 0.0004(3) 0.0060(3) -0.0123(3)
N2 0.0331(11) 0.0371(11) 0.0463(12) -0.0054(9) 0.0003(9) 0.0020(9)
N1 0.0525(15) 0.0389(12) 0.0402(12) -0.0028(9) -0.0093(10) 0.0008(10)
C7 0.0350(16) 0.0393(15) 0.0564(18) -0.0119(11) -0.0064(13) 0.0058(10)
C8 0.0308(16) 0.055(2) 0.086(3) -0.0172(16) -0.0041(17) 0.0064(12)
C11 0.0409(15) 0.0566(18) 0.0539(16) 0.0058(13) 0.0050(12) -0.0003(13)
C9 0.0372(16) 0.062(2) 0.085(3) -0.0148(19) 0.0179(16) -0.0040(15)
C10 0.0501(19) 0.070(2) 0.068(2) -0.0003(17) 0.0192(16) -0.0090(17)
C6 0.0472(17) 0.0433(15) 0.0541(17) -0.0064(12) -0.0167(13) 0.0078(13)
C5 0.083(3) 0.059(2) 0.0453(16) 0.0107(14) -0.0124(16) -0.0102(18)
C4 0.062(2) 0.075(2) 0.0545(19) 0.0024(17) 0.0030(17) -0.0105(19)
C3 0.079(3) 0.088(3) 0.0532(19) -0.0131(18) 0.0101(18) -0.028(2)
C2 0.091(3) 0.121(4) 0.066(2) -0.027(3) 0.023(2) -0.035(3)
C1 0.195(8) 0.136(6) 0.081(4) -0.043(4) 0.041(4) -0.074(6)
O1 0.122(4) 0.511(14) 0.078(3) -0.075(5) 0.023(3) -0.149(6)

_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 N2 2.035(2) . ?
Cu1 N1 2.042(2) . ?
Cu1 Cl1 2.2704(8) . ?
Cu1 Cl2 2.2723(7) . ?
N2 C11 1.319(4) . ?
N2 C7 1.348(4) . ?
N1 C6 1.256(4) . ?
N1 C5 1.469(4) . ?
C7 C8 1.384(6) . ?
C7 C6 1.461(5) . ?
C8 C9 1.374(6) . ?
C11 C10 1.392(4) . ?
C9 C10 1.369(6) . ?
C5 C4 1.483(6) . ?
C4 C3 1.520(5) . ?
C3 C2 1.514(7) . ?
C2 C1 1.425(7) . ?
C1 O1 1.212(7) . ?

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
N2 Cu1 N1 80.16(10) . . ?
N2 Cu1 Cl1 165.59(7) . . ?
N1 Cu1 Cl1 93.48(8) . . ?
N2 Cu1 Cl2 93.13(7) . . ?
N1 Cu1 Cl2 173.03(8) . . ?
Cl1 Cu1 Cl2 93.48(3) . . ?
C11 N2 C7 117.9(3) . . ?
C11 N2 Cu1 129.1(2) . . ?
C7 N2 Cu1 113.0(2) . . ?
C6 N1 C5 119.2(3) . . ?
C6 N1 Cu1 113.6(2) . . ?
C5 N1 Cu1 127.2(2) . . ?
N2 C7 C8 122.6(4) . . ?
N2 C7 C6 114.1(3) . . ?
C8 C7 C6 123.4(4) . . ?
C9 C8 C7 118.9(4) . . ?
N2 C11 C10 122.7(3) . . ?
C10 C9 C8 118.8(3) . . ?
C9 C10 C11 119.2(3) . . ?
N1 C6 C7 119.1(3) . . ?
N1 C5 C4 111.7(3) . . ?
C5 C4 C3 114.7(4) . . ?
C2 C3 C4 109.2(4) . . ?
C1 C2 C3 114.6(5) . . ?
O1 C1 C2 125.1(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.57
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.332
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.087
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_preparation       'Magnetic properties'
