# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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 retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H48 Cu4 N8 O8'
_chemical_formula_weight         1119.10

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   6.8640(14)
_cell_length_b                   23.286(5)
_cell_length_c                   9.758(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.86(2)
_cell_angle_gamma                90.00
_cell_volume                     1426.4(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_absorpt_coefficient_mu    1.523
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            9552
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_av_sigmaI/netI    0.1511
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         33.26
_reflns_number_total             5005
_reflns_number_gt                2225
_reflns_threshold_expression     >2sigma(I)

_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)+(0.0644P)²+9.5405P] 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     SHELXL
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5005
_refine_ls_number_parameters     179
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.2390
_refine_ls_R_factor_gt           0.1240
_refine_ls_wR_factor_ref         0.2950
_refine_ls_wR_factor_gt          0.2595
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_restrained_S_all      1.201
_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 0.58720(16) 0.19558(5) 0.46036(11) 0.0411(4) Uani 1 1 d . . .
O11A O 0.3070(9) 0.1734(3) 0.4431(7) 0.0524(17) Uani 1 1 d . . .
O12A O 0.0043(9) 0.1261(3) 0.3310(7) 0.0540(17) Uani 1 1 d . . .
C1A C 0.1920(12) 0.1384(4) 0.3481(8) 0.040(2) Uani 1 1 d . . .
C2A C 0.2762(14) 0.1081(4) 0.2422(9) 0.045(2) Uani 1 1 d . . .
H2A H 0.1570 0.0880 0.1646 0.054 Uiso 1 1 calc R . .
C3A C 0.3641(12) 0.1524(4) 0.1656(9) 0.0379(19) Uani 1 1 d . . .
O31A O 0.5056(9) 0.1873(3) 0.2450(6) 0.0455(15) Uani 1 1 d . . .
O32A O 0.2953(10) 0.1522(3) 0.0258(6) 0.0518(16) Uani 1 1 d . . .
C4A C 0.4443(17) 0.0643(4) 0.3264(11) 0.056(3) Uani 1 1 d . . .
H41A H 0.3806 0.0356 0.3678 0.067 Uiso 1 1 calc R . .
H42A H 0.5557 0.0833 0.4098 0.067 Uiso 1 1 calc R . .
C5A C 0.547(2) 0.0334(5) 0.2331(13) 0.073(3) Uani 1 1 d . . .
H51A H 0.4388 0.0105 0.1570 0.087 Uiso 1 1 calc R . .
H52A H 0.5962 0.0620 0.1823 0.087 Uiso 1 1 calc R . .
C6A C 0.726(2) -0.0040(5) 0.3204(14) 0.078(3) Uani 1 1 d . . .
H61A H 0.6724 -0.0356 0.3597 0.094 Uiso 1 1 calc R . .
H62A H 0.8241 0.0176 0.4052 0.094 Uiso 1 1 calc R . .
C7A C 0.850(3) -0.0287(7) 0.235(2) 0.121(6) Uani 1 1 d . . .
H71A H 0.7518 -0.0424 0.1394 0.146 Uiso 1 1 calc R . .
H72A H 0.9371 -0.0599 0.2914 0.146 Uiso 1 1 calc R . .
H73A H 0.9383 0.0007 0.2215 0.146 Uiso 1 1 calc R . .
O1B O 0.8884(8) 0.1948(3) 0.4941(6) 0.0448(15) Uani 1 1 d D . .
H1B H 0.912(14) 0.1553(15) 0.472(10) 0.054 Uiso 1 1 d D . .
C1B C 1.0325(12) 0.1945(4) 0.6496(8) 0.045(2) Uani 1 1 d . . .
H11B H 1.1650 0.2134 0.6631 0.054 Uiso 1 1 calc R . .
H12B H 1.0640 0.1554 0.6862 0.054 Uiso 1 1 calc R . .
C2B C 0.9216(13) 0.2267(4) 0.7337(9) 0.047(2) Uani 1 1 d . . .
H21B H 0.9979 0.2211 0.8408 0.056 Uiso 1 1 calc R . .
H22B H 0.9181 0.2675 0.7128 0.056 Uiso 1 1 calc R . .
N1B N 0.6979(11) 0.2036(3) 0.6823(7) 0.0415(17) Uani 1 1 d . . .
H1B H 0.6190 0.2316 0.7008 0.050 Uiso 1 1 calc R . .
C3B C 0.6849(14) 0.1519(4) 0.7689(9) 0.046(2) Uani 1 1 d . . .
H31B H 0.7963 0.1252 0.7745 0.056 Uiso 1 1 calc R . .
H32B H 0.5491 0.1331 0.7152 0.056 Uiso 1 1 calc R . .
C4B C 0.7070(16) 0.1653(4) 0.9249(9) 0.052(2) Uani 1 1 d . . .
H41B H 0.6870 0.1303 0.9715 0.062 Uiso 1 1 calc R . .
H42B H 0.8502 0.1791 0.9832 0.062 Uiso 1 1 calc R . .
O2B O 0.5584(9) 0.2070(3) 0.9277(6) 0.0478(16) Uani 1 1 d D . .
H2B H 0.438(10) 0.189(3) 0.937(11) 0.057 Uiso 1 1 d 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 0.0302(5) 0.0753(8) 0.0210(5) -0.0028(5) 0.0137(4) -0.0018(5)
O11A 0.036(3) 0.092(5) 0.039(3) -0.017(3) 0.024(3) -0.009(3)
O12A 0.033(3) 0.091(5) 0.044(4) -0.017(3) 0.022(3) -0.012(3)
C1A 0.026(4) 0.073(6) 0.020(4) 0.005(4) 0.008(3) 0.003(4)
C2A 0.042(5) 0.066(6) 0.036(5) -0.005(4) 0.025(4) -0.003(4)
C3A 0.023(4) 0.064(6) 0.029(4) 0.000(4) 0.014(3) 0.002(4)
O31A 0.037(3) 0.079(4) 0.023(3) -0.004(3) 0.016(2) -0.010(3)
O32A 0.052(4) 0.081(5) 0.029(3) -0.001(3) 0.022(3) -0.005(3)
C4A 0.064(6) 0.072(7) 0.042(5) 0.009(5) 0.031(5) 0.012(5)
C5A 0.089(9) 0.082(8) 0.067(7) 0.008(6) 0.052(7) 0.026(7)
C6A 0.091(9) 0.079(8) 0.066(8) 0.002(6) 0.032(7) 0.014(7)
C7A 0.151(15) 0.103(11) 0.152(15) -0.010(10) 0.104(13) 0.036(11)
O1B 0.021(2) 0.091(5) 0.022(3) -0.005(3) 0.007(2) 0.003(3)
C1B 0.020(3) 0.085(7) 0.025(4) 0.001(4) 0.003(3) 0.002(4)
C2B 0.034(4) 0.080(7) 0.029(4) -0.005(4) 0.015(4) -0.005(4)
N1B 0.038(4) 0.070(5) 0.021(3) 0.004(3) 0.016(3) 0.006(3)
C3B 0.041(5) 0.074(7) 0.025(4) 0.000(4) 0.014(4) 0.001(4)
C4B 0.062(6) 0.073(7) 0.030(4) 0.009(4) 0.028(4) 0.004(5)
O2B 0.038(3) 0.083(5) 0.031(3) 0.002(3) 0.023(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 O11A 1.932(6) . ?
Cu1 O31A 1.953(5) . ?
Cu1 O1B 1.958(5) . ?
Cu1 N1B 1.993(6) . ?
Cu1 O2B 2.289(7) 4_565 ?
O11A C1A 1.248(10) . ?
O12A C1A 1.263(9) . ?
C1A C2A 1.543(11) . ?
C2A C4A 1.510(13) . ?
C2A C3A 1.534(11) . ?
C2A H2A 0.9800 . ?
C3A O32A 1.250(9) . ?
C3A O31A 1.264(10) . ?
C4A C5A 1.537(13) . ?
C4A H41A 0.9700 . ?
C4A H42A 0.9700 . ?
C5A C6A 1.466(15) . ?
C5A H51A 0.9700 . ?
C5A H52A 0.9700 . ?
C6A C7A 1.518(16) . ?
C6A H61A 0.9700 . ?
C6A H62A 0.9700 . ?
C7A H71A 0.9600 . ?
C7A H72A 0.9600 . ?
C7A H73A 0.9600 . ?
O1B C1B 1.437(9) . ?
O1B H1B 0.97(2) . ?
C1B C2B 1.524(11) . ?
C1B H11B 0.9700 . ?
C1B H12B 0.9700 . ?
C2B N1B 1.508(10) . ?
C2B H21B 0.9700 . ?
C2B H22B 0.9700 . ?
N1B C3B 1.494(11) . ?
N1B H1B 0.9100 . ?
C3B C4B 1.499(11) . ?
C3B H31B 0.9700 . ?
C3B H32B 0.9700 . ?
C4B O2B 1.416(11) . ?
C4B H41B 0.9700 . ?
C4B H42B 0.9700 . ?
O2B Cu1 2.289(7) 4_566 ?
O2B H2B 0.97(2) . ?

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
O11A Cu1 O31A 92.2(2) . . ?
O11A Cu1 O1B 163.5(3) . . ?
O31A Cu1 O1B 90.2(2) . . ?
O11A Cu1 N1B 92.8(3) . . ?
O31A Cu1 N1B 174.8(3) . . ?
O1B Cu1 N1B 84.6(2) . . ?
O11A Cu1 O2B 103.0(3) . 4_565 ?
O31A Cu1 O2B 88.7(2) . 4_565 ?
O1B Cu1 O2B 93.4(2) . 4_565 ?
N1B Cu1 O2B 91.8(3) . 4_565 ?
C1A O11A Cu1 123.2(5) . . ?
O11A C1A O12A 123.4(7) . . ?
O11A C1A C2A 120.1(7) . . ?
O12A C1A C2A 116.5(8) . . ?
C4A C2A C3A 110.8(7) . . ?
C4A C2A C1A 110.8(7) . . ?
C3A C2A C1A 110.3(7) . . ?
C4A C2A H2A 108.3 . . ?
C3A C2A H2A 108.3 . . ?
C1A C2A H2A 108.3 . . ?
O32A C3A O31A 122.0(7) . . ?
O32A C3A C2A 118.7(8) . . ?
O31A C3A C2A 119.4(7) . . ?
C3A O31A Cu1 122.6(5) . . ?
C2A C4A C5A 115.2(8) . . ?
C2A C4A H41A 108.5 . . ?
C5A C4A H41A 108.5 . . ?
C2A C4A H42A 108.5 . . ?
C5A C4A H42A 108.5 . . ?
H41A C4A H42A 107.5 . . ?
C6A C5A C4A 114.4(9) . . ?
C6A C5A H51A 108.7 . . ?
C4A C5A H51A 108.7 . . ?
C6A C5A H52A 108.7 . . ?
C4A C5A H52A 108.7 . . ?
H51A C5A H52A 107.6 . . ?
C5A C6A C7A 115.5(11) . . ?
C5A C6A H61A 108.4 . . ?
C7A C6A H61A 108.4 . . ?
C5A C6A H62A 108.4 . . ?
C7A C6A H62A 108.4 . . ?
H61A C6A H62A 107.5 . . ?
C6A C7A H71A 109.5 . . ?
C6A C7A H72A 109.5 . . ?
H71A C7A H72A 109.5 . . ?
C6A C7A H73A 109.5 . . ?
H71A C7A H73A 109.5 . . ?
H72A C7A H73A 109.5 . . ?
C1B O1B Cu1 114.0(4) . . ?
C1B O1B H1B 97(6) . . ?
Cu1 O1B H1B 103(6) . . ?
O1B C1B C2B 106.6(6) . . ?
O1B C1B H11B 110.4 . . ?
C2B C1B H11B 110.4 . . ?
O1B C1B H12B 110.4 . . ?
C2B C1B H12B 110.4 . . ?
H11B C1B H12B 108.6 . . ?
N1B C2B C1B 108.0(7) . . ?
N1B C2B H21B 110.1 . . ?
C1B C2B H21B 110.1 . . ?
N1B C2B H22B 110.1 . . ?
C1B C2B H22B 110.1 . . ?
H21B C2B H22B 108.4 . . ?
C3B N1B C2B 112.6(7) . . ?
C3B N1B Cu1 117.1(5) . . ?
C2B N1B Cu1 106.5(4) . . ?
C3B N1B H1B 106.7 . . ?
C2B N1B H1B 106.7 . . ?
Cu1 N1B H1B 106.7 . . ?
N1B C3B C4B 113.8(8) . . ?
N1B C3B H31B 108.8 . . ?
C4B C3B H31B 108.8 . . ?
N1B C3B H32B 108.8 . . ?
C4B C3B H32B 108.8 . . ?
H31B C3B H32B 107.7 . . ?
O2B C4B C3B 112.5(7) . . ?
O2B C4B H41B 109.1 . . ?
C3B C4B H41B 109.1 . . ?
O2B C4B H42B 109.1 . . ?
C3B C4B H42B 109.1 . . ?
H41B C4B H42B 107.8 . . ?
C4B O2B Cu1 131.3(6) . 4_566 ?
C4B O2B H2B 111(5) . . ?
Cu1 O2B H2B 117(5) 4_566 . ?

_diffrn_measured_fraction_theta_max 0.910
_diffrn_reflns_theta_full        33.26
_diffrn_measured_fraction_theta_full 0.910
_refine_diff_density_max         2.173
_refine_diff_density_min         -1.662
_refine_diff_density_rms         0.174
_database_code_depnum_ccdc_archive 'CCDC 892041'
