# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 919043'
#TrackingRef 'CUM292BSQUEEZED.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C112 H176 Cu2 N10 O18'
_chemical_formula_weight         2077.71
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           tetragonal
_symmetry_space_group_name_H-M   P4(2)/m
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z+1/2'
'y, -x, z+1/2'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z-1/2'
'-y, x, -z-1/2'
_cell_length_a                   14.8420(10)
_cell_length_b                   14.8420(10)
_cell_length_c                   25.8161(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5686.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9020
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      21.31
_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2240
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   platon
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46647
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         21.31
_reflns_number_total             3281
_reflns_number_gt                2959
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX'
_computing_cell_refinement       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'WinGX Package'
_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.
;
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.010 0.000 0.000 495 194 ' '
2 0.000 -0.006 0.500 494 194 ' '
_platon_squeeze_details          
;
;
_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^)+(0.0951P)^2^+5.1734P] 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    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0077(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3281
_refine_ls_number_parameters     290
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1696
_refine_ls_wR_factor_gt          0.1656
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_restrained_S_all      1.230
_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 0.0000 0.5000 0.15258(2) 0.0260(3) Uani 1 2 d S . .
N2 N 0.6664(2) 0.1322(2) 0.20170(13) 0.0411(9) Uani 1 1 d . . .
C18 C 0.6797(3) 0.1888(3) 0.15308(16) 0.0453(12) Uani 1 1 d . . .
H18A H 0.7051 0.2477 0.1635 0.054 Uiso 1 1 calc R . .
H18B H 0.7251 0.1585 0.1310 0.054 Uiso 1 1 calc R . .
C15 C 0.6208(3) 0.2711(3) 0.25420(17) 0.0460(11) Uani 1 1 d . . .
H15A H 0.6160 0.3112 0.2236 0.055 Uiso 1 1 calc R . .
H15B H 0.6833 0.2745 0.2674 0.055 Uiso 1 1 calc R . .
C16 C 0.5559(3) 0.3028(3) 0.29589(16) 0.0452(11) Uani 1 1 d . . .
H16A H 0.5577 0.2601 0.3254 0.054 Uiso 1 1 calc R . .
H16B H 0.4939 0.3029 0.2818 0.054 Uiso 1 1 calc R . .
C14 C 0.5997(3) 0.1755(3) 0.23840(16) 0.0396(11) Uani 1 1 d . . .
H14A H 0.5395 0.1747 0.2219 0.047 Uiso 1 1 calc R . .
H14B H 0.5961 0.1381 0.2701 0.047 Uiso 1 1 calc R . .
C17 C 0.5793(3) 0.3968(3) 0.31512(18) 0.0548(13) Uani 1 1 d . . .
H17A H 0.6415 0.3974 0.3278 0.082 Uiso 1 1 calc R . .
H17B H 0.5384 0.4135 0.3433 0.082 Uiso 1 1 calc R . .
H17C H 0.5731 0.4400 0.2866 0.082 Uiso 1 1 calc R . .
C22 C 0.6286(3) 0.0397(3) 0.18805(17) 0.0443(11) Uani 1 1 d . . .
H22A H 0.6140 0.0078 0.2207 0.053 Uiso 1 1 calc R . .
H22B H 0.5715 0.0483 0.1689 0.053 Uiso 1 1 calc R . .
C10 C 0.7584(3) 0.1239(3) 0.22803(18) 0.0456(12) Uani 1 1 d . . .
H10A H 0.8006 0.0956 0.2032 0.055 Uiso 1 1 calc R . .
H10B H 0.7810 0.1854 0.2352 0.055 Uiso 1 1 calc R . .
C12 C 0.8569(3) 0.0668(4) 0.2985(3) 0.0743(17) Uani 1 1 d . . .
H12A H 0.8810 0.1286 0.3023 0.089 Uiso 1 1 calc R . .
H12B H 0.8957 0.0342 0.2736 0.089 Uiso 1 1 calc R . .
C19 C 0.5976(4) 0.2057(3) 0.12105(18) 0.0552(13) Uani 1 1 d . . .
H19A H 0.5492 0.2299 0.1434 0.066 Uiso 1 1 calc R . .
H19B H 0.5763 0.1480 0.1062 0.066 Uiso 1 1 calc R . .
C11 C 0.7615(3) 0.0717(3) 0.27698(19) 0.0532(13) Uani 1 1 d . . .
H11A H 0.7389 0.0100 0.2706 0.064 Uiso 1 1 calc R . .
H11B H 0.7216 0.1005 0.3029 0.064 Uiso 1 1 calc R . .
C24 C 0.6410(4) -0.1094(3) 0.1462(2) 0.0739(17) Uani 1 1 d . . .
H24A H 0.6252 -0.1375 0.1798 0.089 Uiso 1 1 calc R . .
H24B H 0.5844 -0.0978 0.1271 0.089 Uiso 1 1 calc R . .
C23 C 0.6892(3) -0.0199(3) 0.1562(2) 0.0593(14) Uani 1 1 d . . .
H23A H 0.7463 -0.0308 0.1749 0.071 Uiso 1 1 calc R . .
H23B H 0.7034 0.0098 0.1229 0.071 Uiso 1 1 calc R . .
C13 C 0.8610(4) 0.0194(6) 0.3508(3) 0.109(3) Uani 1 1 d . . .
H13A H 0.8266 0.0540 0.3763 0.164 Uiso 1 1 calc R . .
H13B H 0.9239 0.0148 0.3620 0.164 Uiso 1 1 calc R . .
H13C H 0.8353 -0.0411 0.3476 0.164 Uiso 1 1 calc R . .
C25 C 0.6988(6) -0.1742(4) 0.1153(4) 0.126(3) Uani 1 1 d . . .
H25A H 0.7144 -0.1469 0.0820 0.188 Uiso 1 1 calc R . .
H25B H 0.6653 -0.2302 0.1094 0.188 Uiso 1 1 calc R . .
H25C H 0.7540 -0.1876 0.1347 0.188 Uiso 1 1 calc R . .
O1 O -0.06811(17) 0.44069(16) 0.20715(9) 0.0327(7) Uani 1 1 d . . .
O2 O -0.1509(2) 0.28473(19) 0.11705(11) 0.0462(8) Uani 1 1 d . . .
O3 O -0.17128(19) 0.33483(18) 0.22057(11) 0.0438(8) Uani 1 1 d . . .
N1 N -0.0558(2) 0.4073(2) 0.10886(12) 0.0315(8) Uani 1 1 d . . .
C3 C -0.0491(3) 0.3959(2) 0.05451(15) 0.0313(10) Uani 1 1 d . . .
C4 C 0.0337(2) 0.3916(2) 0.02779(14) 0.0293(9) Uani 1 1 d . . .
C7 C -0.1284(3) 0.3952(2) 0.02638(15) 0.0326(10) Uani 1 1 d . . .
H7 H -0.1843 0.3946 0.0443 0.039 Uiso 1 1 calc R . .
C2 C -0.1199(3) 0.3766(2) 0.19230(16) 0.0317(10) Uani 1 1 d D . .
C6 C 0.2054(3) 0.3886(2) 0.02699(15) 0.0307(9) Uani 1 1 d . . .
C1 C -0.1111(3) 0.3520(3) 0.13449(16) 0.0348(10) Uani 1 1 d D . .
C5 C 0.1192(2) 0.3871(2) 0.05669(15) 0.0280(9) Uani 1 1 d . . .
O4 O 0.12334(18) 0.3830(2) 0.10418(11) 0.0439(8) Uani 1 1 d . . .
C8 C 0.2874(3) 0.3914(3) 0.05334(16) 0.0385(10) Uani 1 1 d . . .
H8 H 0.2877 0.3910 0.0901 0.046 Uiso 1 1 calc R . .
C9 C 0.3681(3) 0.3946(3) 0.02676(17) 0.0451(11) Uani 1 1 d . . .
H9 H 0.4234 0.3969 0.0452 0.054 Uiso 1 1 calc R . .
C20 C 0.6168(4) 0.2723(3) 0.07713(19) 0.0661(15) Uani 1 1 d D . .
H20A H 0.6729 0.2542 0.0593 0.079 Uiso 1 1 calc R . .
H20B H 0.5670 0.2693 0.0516 0.079 Uiso 1 1 calc R . .
C21 C 0.6265(4) 0.3683(3) 0.0957(2) 0.0703(15) Uani 1 1 d D . .
H21A H 0.5735 0.3850 0.1163 0.105 Uiso 1 1 calc R . .
H21B H 0.6313 0.4087 0.0658 0.105 Uiso 1 1 calc R . .
H21C H 0.6808 0.3737 0.1170 0.105 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 0.0294(5) 0.0237(4) 0.0248(5) 0.000 0.000 -0.0033(3)
N2 0.038(2) 0.036(2) 0.049(2) -0.0024(17) 0.0091(17) -0.0133(16)
C18 0.059(3) 0.036(2) 0.041(3) -0.002(2) 0.021(2) -0.011(2)
C15 0.044(3) 0.048(3) 0.046(3) -0.004(2) 0.013(2) -0.002(2)
C16 0.043(3) 0.055(3) 0.038(3) 0.007(2) 0.003(2) 0.006(2)
C14 0.034(2) 0.043(3) 0.041(2) 0.002(2) 0.007(2) -0.0078(19)
C17 0.069(3) 0.050(3) 0.046(3) 0.004(2) 0.015(2) 0.017(2)
C22 0.050(3) 0.035(2) 0.048(3) 0.001(2) -0.001(2) -0.017(2)
C10 0.035(2) 0.040(2) 0.061(3) -0.011(2) 0.010(2) -0.0113(19)
C12 0.042(3) 0.071(4) 0.110(5) -0.012(4) -0.009(3) -0.002(3)
C19 0.076(4) 0.045(3) 0.044(3) 0.004(2) 0.004(3) -0.019(2)
C11 0.037(3) 0.051(3) 0.072(3) 0.000(3) -0.001(2) -0.011(2)
C24 0.102(5) 0.048(3) 0.071(4) -0.012(3) -0.009(3) -0.020(3)
C23 0.058(3) 0.042(3) 0.077(4) -0.015(2) -0.014(3) -0.005(2)
C13 0.061(4) 0.142(7) 0.125(6) 0.031(5) -0.037(4) -0.002(4)
C25 0.132(6) 0.057(4) 0.187(9) -0.060(5) -0.029(6) 0.011(4)
O1 0.0409(16) 0.0287(15) 0.0285(15) -0.0014(12) 0.0041(12) -0.0049(13)
O2 0.0559(19) 0.0425(18) 0.0403(17) -0.0026(14) 0.0067(14) -0.0221(15)
O3 0.0498(18) 0.0438(17) 0.0376(17) 0.0029(14) 0.0160(15) -0.0151(14)
N1 0.0354(19) 0.0327(18) 0.0263(19) 0.0011(15) 0.0042(15) -0.0102(15)
C3 0.038(2) 0.023(2) 0.033(2) 0.0011(17) 0.000(2) -0.0079(17)
C4 0.034(2) 0.023(2) 0.0308(19) -0.0016(17) 0.0006(18) -0.0026(16)
C7 0.032(2) 0.030(2) 0.036(2) 0.0008(17) 0.0052(18) -0.0119(17)
C2 0.032(2) 0.026(2) 0.037(2) 0.0017(19) 0.004(2) 0.0023(19)
C6 0.035(2) 0.022(2) 0.0345(19) -0.0007(16) -0.0012(18) 0.0002(17)
C1 0.035(2) 0.035(2) 0.035(2) 0.000(2) 0.003(2) -0.008(2)
C5 0.032(2) 0.026(2) 0.026(3) 0.0014(17) -0.0008(18) -0.0001(16)
O4 0.0368(17) 0.067(2) 0.0278(18) 0.0033(14) -0.0001(13) 0.0011(14)
C8 0.041(3) 0.041(2) 0.034(2) 0.0020(19) -0.004(2) 0.0028(19)
C9 0.030(2) 0.059(3) 0.047(2) -0.002(2) -0.0058(19) 0.003(2)
C20 0.092(4) 0.055(3) 0.051(3) 0.001(3) 0.015(3) -0.007(3)
C21 0.067(3) 0.049(3) 0.095(4) 0.012(3) 0.013(3) -0.003(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 O1 1.944(2) 2_565 ?
Cu1 O1 1.944(2) . ?
Cu1 N1 1.963(3) 2_565 ?
Cu1 N1 1.963(3) . ?
N2 C14 1.513(5) . ?
N2 C18 1.523(5) . ?
N2 C22 1.524(5) . ?
N2 C10 1.531(5) . ?
C18 C19 1.494(7) . ?
C15 C14 1.509(6) . ?
C15 C16 1.518(6) . ?
C16 C17 1.521(6) . ?
C22 C23 1.506(7) . ?
C10 C11 1.483(6) . ?
C12 C11 1.522(7) . ?
C12 C13 1.522(9) . ?
C19 C20 1.532(7) . ?
C24 C25 1.515(9) . ?
C24 C23 1.531(7) . ?
O1 C2 1.282(5) . ?
O2 C1 1.244(5) . ?
O3 C2 1.224(5) . ?
N1 C1 1.336(5) . ?
N1 C3 1.417(5) . ?
C3 C7 1.383(5) . ?
C3 C4 1.411(5) . ?
C4 C4 1.435(7) 6 ?
C4 C5 1.474(5) . ?
C7 C7 1.362(8) 6 ?
C2 C1 1.542(6) . ?
C6 C6 1.393(8) 6 ?
C6 C8 1.394(5) . ?
C6 C5 1.491(5) . ?
C5 O4 1.229(4) . ?
C8 C9 1.381(6) . ?
C9 C9 1.381(9) 6 ?
C20 C21 1.510(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
O1 Cu1 O1 87.16(15) 2_565 . ?
O1 Cu1 N1 83.10(11) 2_565 2_565 ?
O1 Cu1 N1 162.40(12) . 2_565 ?
O1 Cu1 N1 162.40(12) 2_565 . ?
O1 Cu1 N1 83.10(11) . . ?
N1 Cu1 N1 109.81(18) 2_565 . ?
C14 N2 C18 111.5(3) . . ?
C14 N2 C22 106.7(3) . . ?
C18 N2 C22 110.7(3) . . ?
C14 N2 C10 109.8(3) . . ?
C18 N2 C10 107.1(3) . . ?
C22 N2 C10 111.0(3) . . ?
C19 C18 N2 116.3(4) . . ?
C14 C15 C16 110.6(3) . . ?
C15 C16 C17 111.7(4) . . ?
C15 C14 N2 115.7(3) . . ?
C23 C22 N2 115.9(3) . . ?
C11 C10 N2 116.7(3) . . ?
C11 C12 C13 112.6(5) . . ?
C18 C19 C20 111.5(4) . . ?
C10 C11 C12 111.5(4) . . ?
C25 C24 C23 112.1(5) . . ?
C22 C23 C24 108.9(4) . . ?
C2 O1 Cu1 115.5(2) . . ?
C1 N1 C3 117.4(3) . . ?
C1 N1 Cu1 113.9(3) . . ?
C3 N1 Cu1 128.6(2) . . ?
C7 C3 C4 119.0(3) . . ?
C7 C3 N1 117.4(3) . . ?
C4 C3 N1 123.4(3) . . ?
C3 C4 C4 119.3(2) . 6 ?
C3 C4 C5 120.3(3) . . ?
C4 C4 C5 120.4(2) 6 . ?
C7 C7 C3 121.7(2) 6 . ?
O3 C2 O1 124.8(4) . . ?
O3 C2 C1 120.7(3) . . ?
O1 C2 C1 114.5(3) . . ?
C6 C6 C8 119.2(2) 6 . ?
C6 C6 C5 120.9(2) 6 . ?
C8 C6 C5 119.9(3) . . ?
O2 C1 N1 127.2(4) . . ?
O2 C1 C2 120.0(3) . . ?
N1 C1 C2 112.7(3) . . ?
O4 C5 C4 123.3(3) . . ?
O4 C5 C6 118.1(3) . . ?
C4 C5 C6 118.5(3) . . ?
C9 C8 C6 121.0(4) . . ?
C8 C9 C9 119.8(2) . 6 ?
C21 C20 C19 113.1(4) . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        21.31
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.158