# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 938644'
_audit_update_record             
;
2013-05-11 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H38 Cu2 N6 O10'
_chemical_formula_weight         913.86

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   8.2580(10)
_cell_length_b                   11.221(2)
_cell_length_c                   21.508(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.190(2)
_cell_angle_gamma                90.00
_cell_volume                     1977.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    639
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      30.63

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             940
_exptl_absorpt_coefficient_mu    1.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6104
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Bruker SADABS 2008/1'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Breeze CCD area-detector'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            31462
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         30.63
_reflns_number_total             6071
_reflns_number_gt                4850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX-II (2008)'
_computing_cell_refinement       'APEX-II (2008)'
_computing_data_reduction        'SAINT (2008)'
_computing_structure_solution    'SIR97 (Giacovazzo and co., 1999)'
_computing_structure_refinement  
'SHELXL97, G. M. Sheldrick, Acta Cryst. A, 2008,A64,112-122.'
_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)+(0.0583P)²+0.4073P] 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         6071
_refine_ls_number_parameters     314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.07720(2) 0.360967(17) 0.018807(8) 0.03275(8) Uani 1 1 d . . .
N1 N -0.01499(16) 0.28303(11) -0.05683(6) 0.0296(3) Uani 1 1 d . . .
N2 N 0.01935(18) 0.33673(12) -0.11222(6) 0.0314(3) Uani 1 1 d . . .
O1 O -0.28328(15) -0.01203(10) -0.08308(5) 0.0358(3) Uani 1 1 d . . .
O2 O -0.3830(2) -0.13643(12) -0.15738(7) 0.0523(4) Uani 1 1 d . . .
O3 O 0.01082(16) 0.23844(11) 0.07051(5) 0.0398(3) Uani 1 1 d . . .
O4 O 0.14050(15) 0.47602(10) -0.04119(5) 0.0362(3) Uani 1 1 d . . .
C1 C -0.3637(2) -0.11684(15) -0.10159(9) 0.0392(4) Uani 1 1 d . . .
C2 C -0.4182(2) -0.18834(17) -0.05244(10) 0.0435(4) Uani 1 1 d . . .
C3 C -0.3816(2) -0.16189(16) 0.00850(10) 0.0391(4) Uani 1 1 d . . .
C4 C -0.4411(3) -0.2396(2) 0.05820(11) 0.0527(5) Uani 1 1 d . . .
H4A H -0.5002 -0.3062 0.0387 0.079 Uiso 1 1 calc R . .
H4B H -0.5116 -0.1940 0.0814 0.079 Uiso 1 1 calc R . .
H4C H -0.3494 -0.2679 0.0861 0.079 Uiso 1 1 calc R . .
C5 C -0.28297(19) -0.05818(14) 0.02595(8) 0.0342(3) Uani 1 1 d . . .
C6 C -0.23731(19) 0.01477(14) -0.02102(7) 0.0306(3) Uani 1 1 d . . .
C7 C -0.14127(19) 0.11860(13) -0.00981(7) 0.0291(3) Uani 1 1 d . . .
C8 C -0.0834(2) 0.14805(14) 0.05372(8) 0.0327(3) Uani 1 1 d . . .
C9 C -0.1291(2) 0.07211(17) 0.10157(8) 0.0417(4) Uani 1 1 d . . .
C10 C -0.2247(2) -0.02578(17) 0.08805(9) 0.0410(4) Uani 1 1 d . . .
C11 C -0.10006(19) 0.18614(14) -0.06237(7) 0.0301(3) Uani 1 1 d . . .
C12 C 0.09915(18) 0.43615(14) -0.09805(7) 0.0294(3) Uani 1 1 d . . .
C13 C 0.14378(19) 0.50971(14) -0.15081(7) 0.0313(3) Uani 1 1 d . . .
C14 C 0.0844(2) 0.48275(18) -0.21265(8) 0.0420(4) Uani 1 1 d . . .
C15 C 0.1193(3) 0.5566(2) -0.26070(9) 0.0549(5) Uani 1 1 d . . .
C16 C 0.2159(3) 0.6560(2) -0.24798(10) 0.0531(5) Uani 1 1 d . . .
C17 C 0.2777(3) 0.68287(19) -0.18728(10) 0.0493(5) Uani 1 1 d . . .
C18 C 0.2407(2) 0.61036(17) -0.13881(9) 0.0413(4) Uani 1 1 d . . .
O1S O 0.21670(15) 0.43757(12) 0.08854(5) 0.0404(3) Uani 1 1 d . . .
C1S C 0.2318(2) 0.39953(17) 0.14370(8) 0.0386(4) Uani 1 1 d . . .
N1S N 0.31675(19) 0.45502(16) 0.19072(7) 0.0441(4) Uani 1 1 d . . .
C2S C 0.3306(3) 0.4056(3) 0.25402(10) 0.0670(6) Uani 1 1 d . . .
H2S1 H 0.2822 0.3277 0.2526 0.100 Uiso 1 1 calc R . .
H2S2 H 0.2750 0.4566 0.2802 0.100 Uiso 1 1 calc R . .
H2S3 H 0.4437 0.3999 0.2708 0.100 Uiso 1 1 calc R . .
C3S C 0.3958(3) 0.5677(2) 0.18160(13) 0.0694(7) Uani 1 1 d . . .
H3S1 H 0.3632 0.5956 0.1397 0.104 Uiso 1 1 calc R . .
H3S2 H 0.5121 0.5572 0.1880 0.104 Uiso 1 1 calc R . .
H3S3 H 0.3646 0.6250 0.2110 0.104 Uiso 1 1 calc R . .
H2 H -0.472(3) -0.253(2) -0.0649(12) 0.063(7) Uiso 1 1 d . . .
H9 H -0.090(3) 0.097(2) 0.1458(11) 0.054(6) Uiso 1 1 d . . .
H10 H -0.242(2) -0.0756(19) 0.1220(10) 0.039(5) Uiso 1 1 d . . .
H11 H -0.139(2) 0.1573(17) -0.1028(10) 0.033(5) Uiso 1 1 d . . .
H14 H 0.019(3) 0.418(2) -0.2214(10) 0.050(6) Uiso 1 1 d . . .
H15 H 0.079(3) 0.539(2) -0.3024(12) 0.068(7) Uiso 1 1 d . . .
H16 H 0.239(3) 0.703(2) -0.2803(11) 0.063(7) Uiso 1 1 d . . .
H17 H 0.345(3) 0.749(2) -0.1785(11) 0.060(7) Uiso 1 1 d . . .
H18 H 0.283(3) 0.624(2) -0.0999(13) 0.066(8) Uiso 1 1 d . . .
H1S H 0.176(2) 0.3206(18) 0.1533(9) 0.031(5) Uiso 1 1 d . . .


_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 O3 1.8921(12) . ?
Cu1 N1 1.9186(13) . ?
Cu1 O4 1.9426(12) . ?
Cu1 O1S 1.9706(12) . ?
N1 C11 1.292(2) . ?
N1 N2 1.3954(18) . ?
N2 C12 1.312(2) . ?
O1 C6 1.3744(19) . ?
O1 C1 1.384(2) . ?
O2 C1 1.211(2) . ?
O3 C8 1.302(2) . ?
O4 C12 1.3069(18) . ?
C1 C2 1.443(3) . ?
C2 C3 1.341(3) . ?
C2 H2 0.88(3) . ?
C3 C5 1.443(2) . ?
C3 C4 1.509(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.389(2) . ?
C5 C10 1.409(3) . ?
C6 C7 1.413(2) . ?
C7 C8 1.429(2) . ?
C7 C11 1.437(2) . ?
C8 C9 1.423(2) . ?
C9 C10 1.363(3) . ?
C9 H9 1.01(2) . ?
C10 H10 0.95(2) . ?
C11 H11 0.95(2) . ?
C12 C13 1.486(2) . ?
C13 C18 1.390(2) . ?
C13 C14 1.392(2) . ?
C14 C15 1.383(3) . ?
C14 H14 0.91(2) . ?
C15 C16 1.379(3) . ?
C15 H15 0.94(3) . ?
C16 C17 1.374(3) . ?
C16 H16 0.91(3) . ?
C17 C18 1.386(3) . ?
C17 H17 0.93(3) . ?
C18 H18 0.88(3) . ?
O1S C1S 1.252(2) . ?
C1S N1S 1.313(2) . ?
C1S H1S 1.03(2) . ?
N1S C3S 1.447(3) . ?
N1S C2S 1.461(3) . ?
C2S H2S1 0.9600 . ?
C2S H2S2 0.9600 . ?
C2S H2S3 0.9600 . ?
C3S H3S1 0.9600 . ?
C3S H3S2 0.9600 . ?
C3S H3S3 0.9600 . ?

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
O3 Cu1 N1 93.08(5) . . ?
O3 Cu1 O4 174.34(5) . . ?
N1 Cu1 O4 81.42(5) . . ?
O3 Cu1 O1S 93.12(5) . . ?
N1 Cu1 O1S 167.52(5) . . ?
O4 Cu1 O1S 92.03(5) . . ?
C11 N1 N2 116.81(13) . . ?
C11 N1 Cu1 127.97(11) . . ?
N2 N1 Cu1 115.19(10) . . ?
C12 N2 N1 108.58(12) . . ?
C6 O1 C1 121.97(13) . . ?
C8 O3 Cu1 127.61(11) . . ?
C12 O4 Cu1 109.49(10) . . ?
O2 C1 O1 116.00(16) . . ?
O2 C1 C2 127.62(17) . . ?
O1 C1 C2 116.36(16) . . ?
C3 C2 C1 122.67(17) . . ?
C3 C2 H2 121.7(17) . . ?
C1 C2 H2 115.5(17) . . ?
C2 C3 C5 118.93(16) . . ?
C2 C3 C4 120.73(18) . . ?
C5 C3 C4 120.34(18) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 116.47(16) . . ?
C6 C5 C3 118.82(16) . . ?
C10 C5 C3 124.69(16) . . ?
O1 C6 C5 120.69(15) . . ?
O1 C6 C7 115.28(13) . . ?
C5 C6 C7 124.03(15) . . ?
C6 C7 C8 117.85(14) . . ?
C6 C7 C11 118.94(14) . . ?
C8 C7 C11 123.14(14) . . ?
O3 C8 C9 118.00(15) . . ?
O3 C8 C7 124.21(15) . . ?
C9 C8 C7 117.77(15) . . ?
C10 C9 C8 121.83(17) . . ?
C10 C9 H9 122.5(14) . . ?
C8 C9 H9 115.7(14) . . ?
C9 C10 C5 122.02(16) . . ?
C9 C10 H10 116.9(13) . . ?
C5 C10 H10 120.9(13) . . ?
N1 C11 C7 123.44(14) . . ?
N1 C11 H11 119.3(12) . . ?
C7 C11 H11 117.2(12) . . ?
O4 C12 N2 124.98(14) . . ?
O4 C12 C13 117.62(13) . . ?
N2 C12 C13 117.40(13) . . ?
C18 C13 C14 118.67(16) . . ?
C18 C13 C12 120.11(14) . . ?
C14 C13 C12 121.16(14) . . ?
C15 C14 C13 120.18(17) . . ?
C15 C14 H14 119.8(14) . . ?
C13 C14 H14 120.0(14) . . ?
C16 C15 C14 120.39(19) . . ?
C16 C15 H15 119.0(16) . . ?
C14 C15 H15 120.6(17) . . ?
C17 C16 C15 120.19(19) . . ?
C17 C16 H16 120.6(16) . . ?
C15 C16 H16 119.2(16) . . ?
C16 C17 C18 119.67(18) . . ?
C16 C17 H17 120.5(15) . . ?
C18 C17 H17 119.8(15) . . ?
C17 C18 C13 120.88(17) . . ?
C17 C18 H18 120.7(17) . . ?
C13 C18 H18 118.3(17) . . ?
C1S O1S Cu1 123.50(12) . . ?
O1S C1S N1S 123.25(18) . . ?
O1S C1S H1S 119.2(10) . . ?
N1S C1S H1S 117.6(10) . . ?
C1S N1S C3S 121.08(18) . . ?
C1S N1S C2S 120.62(19) . . ?
C3S N1S C2S 118.29(19) . . ?
N1S C2S H2S1 109.5 . . ?
N1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
N1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
N1S C3S H3S1 109.5 . . ?
N1S C3S H3S2 109.5 . . ?
H3S1 C3S H3S2 109.5 . . ?
N1S C3S H3S3 109.5 . . ?
H3S1 C3S H3S3 109.5 . . ?
H3S2 C3S H3S3 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.63
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.069
