# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_p3221
_database_code_depnum_ccdc_archive 'CCDC 1042998'
_audit_update_record             
;
2015-01-12 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H42 Cl2 Cu N10 O7'
_chemical_formula_weight         693.10

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'
Cu Cu 0.3201 1.2651 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P3(2)21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'

_cell_length_a                   12.3060(6)
_cell_length_b                   12.3060(6)
_cell_length_c                   18.4537(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2420.18(19)
_cell_formula_units_Z            3
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1089
_exptl_absorpt_coefficient_mu    0.897
_exptl_absorpt_correction_T_min  0.81318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      295(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22441
_diffrn_reflns_av_R_equivalents  0.1369
_diffrn_reflns_av_sigmaI/netI    0.1006
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.49
_diffrn_reflns_theta_max         25.64
_reflns_number_total             3048
_reflns_number_gt                2025
_reflns_threshold_expression     >2sigma(I)
_chemical_absolute_configuration s

_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 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)+(0.0413P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_number_reflns         3048
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_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 0.71277(10) 0.0000 0.1667 0.0590(3) Uani 1 2 d S . .
N1 N -0.0822(5) 0.0000 0.1667 0.0458(15) Uani 1 2 d S . .
C1 C -0.0331(5) -0.0168(5) 0.1070(3) 0.0526(14) Uani 1 1 d . . .
H1 H -0.0772 -0.0294 0.0639 0.063 Uiso 1 1 calc R . .
C2 C 0.0780(5) -0.0169(5) 0.1038(3) 0.0515(14) Uani 1 1 d . . .
H2 H 0.1079 -0.0283 0.0598 0.062 Uiso 1 1 calc R . .
C3 C 0.1445(6) 0.0000 0.1667 0.0426(16) Uani 1 2 d S . .
C4 C 0.2670(6) 0.0000 0.1667 0.0449(19) Uani 1 2 d S . .
C5 C 0.4575(6) 0.0415(7) 0.1117(4) 0.0749(19) Uani 1 1 d . . .
H5 H 0.5100 0.0711 0.0716 0.090 Uiso 1 1 calc R . .
C6 C 0.3472(6) 0.0443(6) 0.1093(3) 0.0631(17) Uani 1 1 d . . .
H6 H 0.3276 0.0762 0.0688 0.076 Uiso 1 1 calc R . .
N2 N 0.4938(6) 0.0000 0.1667 0.076(2) Uani 1 2 d S . .
O1 O 0.7439(4) 0.0616(3) 0.06813(16) 0.0514(9) Uani 1 1 d . . .
O2 O 0.8105(4) 0.2301(4) 0.00060(18) 0.0681(12) Uani 1 1 d . . .
N3 N 0.6105(4) -0.1784(3) 0.1399(2) 0.0410(10) Uani 1 1 d . . .
H3A H 0.5449 -0.1894 0.1128 0.049 Uiso 1 1 calc R . .
H3B H 0.6570 -0.2010 0.1131 0.049 Uiso 1 1 calc R . .
C8 C 0.5931(5) -0.3652(5) 0.2036(3) 0.0486(14) Uani 1 1 d . . .
H8A H 0.5529 -0.4177 0.1617 0.058 Uiso 1 1 calc R . .
H8B H 0.5575 -0.4163 0.2466 0.058 Uiso 1 1 calc R . .
N7 N 0.9154(4) -0.3437(5) 0.0613(2) 0.0621(13) Uani 1 1 d . . .
H7A H 0.8369 -0.3681 0.0568 0.074 Uiso 1 1 calc R . .
H7B H 0.9637 -0.3176 0.0240 0.074 Uiso 1 1 calc R . .
C7 C 0.5639(5) -0.2589(4) 0.2047(2) 0.0425(12) Uani 1 1 d . . .
H7 H 0.4724 -0.2975 0.2048 0.051 Uiso 1 1 calc R . .
N6 N 1.0821(4) -0.3091(4) 0.1301(2) 0.0568(12) Uani 1 1 d . . .
H6A H 1.1139 -0.3106 0.1713 0.068 Uiso 1 1 calc R . .
H6B H 1.1288 -0.2833 0.0922 0.068 Uiso 1 1 calc R . .
C12 C 0.7923(5) 0.1807(5) 0.0602(3) 0.0454(12) Uani 1 1 d . . .
C11 C 0.9614(6) -0.3464(5) 0.1251(3) 0.0482(13) Uani 1 1 d . . .
C9 C 0.7331(5) -0.3200(5) 0.2010(3) 0.0507(14) Uani 1 1 d . . .
H9A H 0.7712 -0.2803 0.2467 0.061 Uiso 1 1 calc R . .
H9B H 0.7718 -0.2577 0.1630 0.061 Uiso 1 1 calc R . .
N5 N 0.8910(5) -0.3855(4) 0.1832(2) 0.0570(13) Uani 1 1 d . . .
H5A H 0.9272 -0.3859 0.2230 0.068 Uiso 1 1 calc R . .
C10 C 0.7583(5) -0.4281(5) 0.1868(3) 0.0571(15) Uani 1 1 d . . .
H10A H 0.7206 -0.4898 0.2252 0.068 Uiso 1 1 calc R . .
H10B H 0.7190 -0.4686 0.1414 0.068 Uiso 1 1 calc R . .
Cl1 Cl 0.6821(2) 0.6821(2) 0.0000 0.0771(7) Uani 0.98 2 d SP . .
Cl2 Cl 0.2699(3) 0.2699(3) 0.0000 0.0743(10) Uani 0.61 2 d SP . .
Cl3 Cl 0.7216(5) 0.3825(5) -0.0506(3) 0.1024(17) Uani 0.20 1 d P . .
O3W O 0.7216(5) 0.3825(5) -0.0506(3) 0.1024(17) Uani 0.50 1 d P . .
O1W O 1.1177(11) -0.3223(11) 0.3054(6) 0.032(5) Uiso 0.272(13) 1 d P . .
O2W O 1.1528(6) -0.3860(7) 0.2866(3) 0.086(3) Uani 0.728(13) 1 d P . .


_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 O1 1.933(3) 5 ?
Cu1 N3 1.971(4) 5 ?
Cu1 N3 1.971(4) . ?
N1 C1 1.321(6) 5 ?
N1 C1 1.321(6) . ?
C1 C2 1.369(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(6) . ?
C2 H2 0.9300 . ?
C3 C2 1.375(6) 5 ?
C3 C4 1.508(10) . ?
C4 C6 1.362(6) 5 ?
C4 C6 1.362(6) . ?
C5 N2 1.310(7) . ?
C5 C6 1.376(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 C5 1.310(7) 5 ?
O1 C12 1.286(6) . ?
O2 C12 1.221(5) . ?
N3 C7 1.474(5) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
C8 C7 1.519(7) . ?
C8 C9 1.524(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N7 C11 1.315(6) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
C7 C12 1.517(7) 5 ?
C7 H7 0.9800 . ?
N6 C11 1.320(6) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
C12 C7 1.517(7) 5 ?
C11 N5 1.309(6) . ?
C9 C10 1.532(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N5 C10 1.446(7) . ?
N5 H5A 0.8600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?


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
O1 Cu1 N3 95.28(15) 5 5 ?
O1 Cu1 N3 84.74(14) 5 . ?
N3 Cu1 N3 170.6(2) 5 . ?
C1 N1 C1 115.3(7) 5 . ?
N1 C1 C2 124.8(5) . . ?
N1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C1 C2 C3 118.9(6) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C2 117.4(7) 5 . ?
C2 C3 C4 121.3(4) 5 . ?
C2 C3 C4 121.3(4) . . ?
C6 C4 C6 116.8(8) 5 . ?
C6 C4 C3 121.6(4) 5 . ?
C6 C4 C3 121.6(4) . . ?
N2 C5 C6 124.7(7) . . ?
N2 C5 H5 117.7 . . ?
C6 C5 H5 117.7 . . ?
C4 C6 C5 119.4(7) . . ?
C4 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C5 N2 C5 115.2(8) 5 . ?
C7 N3 Cu1 111.3(3) . . ?
C7 N3 H3A 109.4 . . ?
Cu1 N3 H3A 109.4 . . ?
C7 N3 H3B 109.4 . . ?
Cu1 N3 H3B 109.4 . . ?
H3A N3 H3B 108.0 . . ?
C7 C8 C9 113.4(4) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C11 N7 H7A 120.0 . . ?
C11 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
N3 C7 C8 112.9(4) . . ?
N3 C7 C12 110.6(4) . 5 ?
C8 C7 C12 112.0(4) . 5 ?
N3 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
C12 C7 H7 107.0 5 . ?
C11 N6 H6A 120.0 . . ?
C11 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
O2 C12 O1 122.4(5) . . ?
O2 C12 C7 120.5(5) . 5 ?
O1 C12 C7 117.0(4) . 5 ?
N5 C11 N7 121.9(5) . . ?
N5 C11 N6 119.6(5) . . ?
N7 C11 N6 118.6(5) . . ?
C8 C9 C10 111.8(5) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C11 N5 C10 126.2(5) . . ?
C11 N5 H5A 116.9 . . ?
C10 N5 H5A 116.9 . . ?
N5 C10 C9 112.0(5) . . ?
N5 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N5 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?


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
N3 H3A Cl3 0.90 2.08 2.941(6) 159.9 4_545
N3 H3B Cl1 0.90 2.64 3.450(4) 150.5 1_545
N7 H7A Cl1 0.86 2.51 3.245(5) 144.4 1_545
N7 H7B O1 0.86 2.00 2.857(6) 174.1 4_645
N6 H6A O2W 0.86 2.46 3.288(7) 161.6 .
N6 H6A O1W 0.86 2.48 3.279(12) 154.9 .
N6 H6B O2 0.86 2.09 2.937(6) 166.9 4_645
N5 H5A Cl2 0.86 2.39 3.097(5) 139.9 3_655
N5 H5A O1W 0.86 2.57 3.362(12) 154.2 .
N5 H5A O1W 0.86 2.63 3.346(12) 142.0 6_765

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.64
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.059
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
