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

#######################################################################
#
#                 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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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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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            'C28 H32 Cu N4 O7'
_chemical_formula_weight         600.12

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3326(4)
_cell_length_b                   10.3780(5)
_cell_length_c                   16.5929(9)
_cell_angle_alpha                87.460(3)
_cell_angle_beta                 77.784(3)
_cell_angle_gamma                74.322(3)
_cell_volume                     1350.09(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4896
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      24.65

_exptl_crystal_description       column
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             626
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7817
_exptl_absorpt_correction_T_max  0.9186
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'

_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20299
_diffrn_reflns_av_R_equivalents  0.1066
_diffrn_reflns_av_sigmaI/netI    0.1050
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5302
_reflns_number_gt                3211
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.1048P)²+0.4275P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5302
_refine_ls_number_parameters     383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.2012
_refine_ls_wR_factor_gt          0.1670
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
Cu Cu 0.22227(7) 0.39423(7) 0.42221(4) 0.0333(2) Uani 1 1 d . . .
O2 O 0.4548(5) 0.2075(4) 0.8014(2) 0.0479(11) Uani 1 1 d . . .
O3 O 0.4536(4) 0.4078(3) 0.36556(19) 0.0248(7) Uani 1 1 d . . .
O4 O 0.4925(4) 0.1998(3) 0.3205(2) 0.0296(8) Uani 1 1 d . . .
O5 O 0.8123(5) 0.4123(4) 0.5216(3) 0.0562(12) Uani 1 1 d . . .
O6 O 1.0462(5) 0.2973(4) 0.4430(3) 0.0593(13) Uani 1 1 d . . .
N1 N 0.1288(5) 0.4633(5) 0.3224(3) 0.0383(11) Uani 1 1 d . . .
N2 N 0.1562(7) 0.3043(6) 0.1268(3) 0.0539(15) Uani 1 1 d . . .
H2A H 0.2438 0.2427 0.1347 0.065 Uiso 1 1 calc R A 1
N3 N 0.3173(5) 0.2920(4) 0.5147(2) 0.0322(10) Uani 1 1 d . . .
N4 N 0.4968(5) 0.3386(4) 0.6898(2) 0.0307(10) Uani 1 1 d . . .
H4A H 0.5346 0.4059 0.6716 0.037 Uiso 1 1 calc R . .
C1 C 0.1591(6) 0.3753(6) 0.2604(3) 0.0363(13) Uani 1 1 d . . .
H1A H 0.2240 0.2886 0.2665 0.044 Uiso 1 1 calc R B .
C2 C 0.1005(7) 0.4051(6) 0.1884(4) 0.0398(14) Uani 1 1 d . . .
C3 C 0.0005(8) 0.5299(8) 0.1798(5) 0.0564(18) Uani 1 1 d . . .
H3A H -0.0425 0.5528 0.1323 0.068 Uiso 1 1 calc R B .
C4 C -0.0360(7) 0.6219(7) 0.2428(5) 0.0536(18) Uani 1 1 d . . .
H4B H -0.1061 0.7074 0.2385 0.064 Uiso 1 1 calc R . .
C5 C 0.0314(7) 0.5875(7) 0.3126(4) 0.0499(16) Uani 1 1 d . . .
H5A H 0.0089 0.6517 0.3538 0.060 Uiso 1 1 calc R B .
O1 O -0.0209(13) 0.3618(9) 0.0450(5) 0.053(2) Uani 0.60 1 d P B 1
C6 C 0.1046(14) 0.2822(11) 0.0592(6) 0.029(2) Uani 0.60 1 d P B 1
C7 C 0.2077(13) 0.1674(10) 0.0014(5) 0.035(2) Uani 0.60 1 d P B 1
H7A H 0.2502 0.0906 0.0339 0.042 Uiso 0.60 1 calc PR B 1
H7B H 0.3054 0.1921 -0.0316 0.042 Uiso 0.60 1 calc PR B 1
C8 C 0.1098(15) 0.1268(12) -0.0558(5) 0.043(3) Uani 0.60 1 d P B 1
H8A H 0.0496 0.2066 -0.0807 0.051 Uiso 0.60 1 calc PR B 1
H8B H 0.1904 0.0708 -0.0998 0.051 Uiso 0.60 1 calc PR B 1
C9 C -0.0172(15) 0.0520(11) -0.0141(6) 0.044(3) Uani 0.60 1 d P . 1
H9A H -0.0940 0.1107 0.0297 0.052 Uiso 1 1 calc R . 1
H9B H -0.0840 0.0455 -0.0543 0.052 Uiso 1 1 calc R . 1
O1' O -0.117(2) 0.3998(17) 0.0783(10) 0.083(5) Uiso 0.40 1 d P B 2
C6' C 0.023(4) 0.328(3) 0.0708(16) 0.055(8) Uiso 0.40 1 d P B 2
C7' C 0.115(3) 0.233(3) 0.0038(16) 0.080(7) Uiso 0.40 1 d P B 2
H7'A H 0.1779 0.1529 0.0269 0.097 Uiso 0.40 1 calc PR B 2
H7'B H 0.1973 0.2720 -0.0320 0.097 Uiso 0.40 1 calc PR B 2
C8' C 0.005(3) 0.193(3) -0.0490(16) 0.098(9) Uiso 0.40 1 d P B 2
H8'A H -0.0713 0.2736 -0.0653 0.118 Uiso 0.40 1 calc PR B 2
H8'B H 0.0791 0.1486 -0.0988 0.118 Uiso 0.40 1 calc PR B 2
C9' C -0.099(3) 0.102(3) -0.0053(19) 0.092(10) Uiso 0.40 1 d P B 2
C10 C 0.3810(6) 0.3449(5) 0.5697(3) 0.0273(11) Uani 1 1 d . . .
H10A H 0.3854 0.4335 0.5637 0.033 Uiso 1 1 calc R . .
C11 C 0.4398(6) 0.2729(5) 0.6344(3) 0.0314(12) Uani 1 1 d . . .
C12 C 0.4399(8) 0.1373(6) 0.6419(3) 0.0429(14) Uani 1 1 d . . .
H12A H 0.4827 0.0852 0.6835 0.051 Uiso 1 1 calc R . .
C13 C 0.3747(9) 0.0843(6) 0.5857(4) 0.0499(17) Uani 1 1 d . . .
H13A H 0.3714 -0.0047 0.5898 0.060 Uiso 1 1 calc R . .
C14 C 0.3145(8) 0.1619(6) 0.5236(4) 0.0443(15) Uani 1 1 d . . .
H14A H 0.2704 0.1240 0.4865 0.053 Uiso 1 1 calc R . .
C15 C 0.4982(6) 0.3058(5) 0.7701(3) 0.0332(12) Uani 1 1 d . D .
C16 C 0.5590(8) 0.3971(6) 0.8169(3) 0.0426(14) Uani 1 1 d . . .
H16A H 0.5103 0.4891 0.8029 0.051 Uiso 1 1 calc R C 1
H16B H 0.6819 0.3783 0.8004 0.051 Uiso 1 1 calc R C 1
C17 C 0.5108(15) 0.3811(12) 0.9086(6) 0.030(3) Uiso 0.50 1 d P D 1
H17A H 0.3876 0.4019 0.9250 0.036 Uiso 0.50 1 calc PR D 1
H17B H 0.5566 0.2883 0.9221 0.036 Uiso 0.50 1 calc PR D 1
C18 C 0.5736(16) 0.4683(13) 0.9575(7) 0.038(3) Uiso 0.50 1 d P . 1
H18A H 0.6005 0.5411 0.9234 0.046 Uiso 0.50 1 calc PR . 1
H18B H 0.6772 0.4163 0.9736 0.046 Uiso 0.50 1 calc PR . 1
C17' C 0.449(2) 0.4315(16) 0.9045(9) 0.058(4) Uiso 0.50 1 d P D 2
H17C H 0.3324 0.4748 0.9003 0.069 Uiso 0.50 1 calc PR D 2
H17D H 0.4493 0.3492 0.9346 0.069 Uiso 0.50 1 calc PR D 2
C18' C 0.5108(16) 0.5229(13) 0.9532(7) 0.035(3) Uiso 0.50 1 d P . 2
H18C H 0.4448 0.6149 0.9500 0.041 Uiso 0.50 1 calc PR . 2
H18D H 0.6295 0.5175 0.9301 0.041 Uiso 0.50 1 calc PR . 2
C19 C 0.5445(6) 0.2993(5) 0.3259(3) 0.0243(11) Uani 1 1 d . . .
C20 C 0.7278(6) 0.2989(5) 0.2848(3) 0.0297(12) Uani 1 1 d . . .
H20A H 0.7345 0.3130 0.2262 0.036 Uiso 1 1 calc R . .
H20B H 0.7560 0.3729 0.3070 0.036 Uiso 1 1 calc R . .
C21 C 0.8566(6) 0.1710(5) 0.2973(3) 0.0252(11) Uani 1 1 d . . .
C22 C 0.9415(6) 0.0843(5) 0.2305(3) 0.0292(12) Uani 1 1 d . . .
H22A H 0.9157 0.1058 0.1789 0.035 Uiso 1 1 calc R . .
C23 C 1.0625(6) -0.0323(5) 0.2396(3) 0.0339(12) Uani 1 1 d . . .
H23A H 1.1176 -0.0887 0.1943 0.041 Uiso 1 1 calc R . .
C24 C 1.1018(7) -0.0653(6) 0.3154(3) 0.0379(13) Uani 1 1 d . . .
H24A H 1.1841 -0.1437 0.3219 0.045 Uiso 1 1 calc R . .
C25 C 1.0183(7) 0.0186(5) 0.3816(3) 0.0351(13) Uani 1 1 d . . .
H25A H 1.0456 -0.0044 0.4328 0.042 Uiso 1 1 calc R . .
C26 C 0.8939(5) 0.1370(5) 0.3749(3) 0.0231(10) Uani 1 1 d . . .
C27 C 0.8019(6) 0.2229(5) 0.4506(3) 0.0239(10) Uani 1 1 d . . .
H27A H 0.7830 0.1646 0.4969 0.029 Uiso 1 1 calc R . .
H27B H 0.6911 0.2739 0.4417 0.029 Uiso 1 1 calc R . .
C28 C 0.8941(6) 0.3205(5) 0.4739(3) 0.0219(10) Uani 1 1 d . . .
O7 O 0.4619(7) 0.0892(6) 0.1712(3) 0.0513(14) Uani 0.80 1 d P . .
O7' O 0.449(4) 0.174(3) 0.1502(18) 0.081(9) Uiso 0.20 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
Cu O6 1.959(4) 1_455 ?
Cu O3 1.997(3) . ?
Cu N1 2.001(5) . ?
Cu N3 2.006(5) . ?
Cu O5 2.173(4) 2_666 ?
O2 C15 1.231(6) . ?
O3 C19 1.291(6) . ?
O4 C19 1.236(5) . ?
O5 C28 1.219(6) . ?
O5 Cu 2.173(4) 2_666 ?
O6 C28 1.224(6) . ?
O6 Cu 1.959(4) 1_655 ?
N1 C1 1.343(7) . ?
N1 C5 1.348(7) . ?
N2 C6 1.333(10) . ?
N2 C2 1.409(8) . ?
N2 C6' 1.56(3) . ?
N2 H2A 0.8600 . ?
N3 C10 1.350(6) . ?
N3 C14 1.358(7) . ?
N4 C15 1.360(6) . ?
N4 C11 1.397(6) . ?
N4 H4A 0.8600 . ?
C1 C2 1.375(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.358(9) . ?
C3 C4 1.376(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(9) . ?
C4 H4B 0.9300 . ?
C5 H5A 0.9300 . ?
O1 C6 1.205(15) . ?
C6 C7 1.509(15) . ?
C7 C8 1.514(12) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.512(13) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C9 1.15(2) 2 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O1' C6' 1.18(3) . ?
C6' C7' 1.45(4) . ?
C7' C8' 1.53(3) . ?
C7' H7'A 0.9700 . ?
C7' H7'B 0.9700 . ?
C8' C9' 1.52(4) . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C10 C11 1.380(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.407(7) . ?
C12 C13 1.373(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.375(9) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.500(7) . ?
C16 C17 1.504(12) . ?
C16 C17' 1.545(15) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.501(16) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C18 1.69(2) 2_667 ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17' C18' 1.524(18) . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
C18' C18' 1.59(2) 2_667 ?
C18' H18C 0.9700 . ?
C18' H18D 0.9700 . ?
C19 C20 1.534(6) . ?
C20 C21 1.502(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C26 1.396(6) . ?
C21 C22 1.397(7) . ?
C22 C23 1.375(7) . ?
C22 H22A 0.9300 . ?
C23 C24 1.373(7) . ?
C23 H23A 0.9300 . ?
C24 C25 1.372(7) . ?
C24 H24A 0.9300 . ?
C25 C26 1.395(7) . ?
C25 H25A 0.9300 . ?
C26 C27 1.511(6) . ?
C27 C28 1.531(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
O7 O7' 0.92(3) . ?

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
O6 Cu O3 150.30(15) 1_455 . ?
O6 Cu N1 85.33(19) 1_455 . ?
O3 Cu N1 90.86(15) . . ?
O6 Cu N3 88.00(19) 1_455 . ?
O3 Cu N3 90.94(15) . . ?
N1 Cu N3 169.52(17) . . ?
O6 Cu O5 122.94(15) 1_455 2_666 ?
O3 Cu O5 86.76(14) . 2_666 ?
N1 Cu O5 97.00(19) . 2_666 ?
N3 Cu O5 93.41(17) . 2_666 ?
C19 O3 Cu 112.5(3) . . ?
C28 O5 Cu 151.6(4) . 2_666 ?
C28 O6 Cu 137.7(4) . 1_655 ?
C1 N1 C5 116.7(5) . . ?
C1 N1 Cu 116.7(4) . . ?
C5 N1 Cu 126.6(4) . . ?
C6 N2 C2 134.9(7) . . ?
C6 N2 C6' 27.0(9) . . ?
C2 N2 C6' 108.7(12) . . ?
C6 N2 H2A 112.6 . . ?
C2 N2 H2A 112.6 . . ?
C6' N2 H2A 137.9 . . ?
C10 N3 C14 117.8(5) . . ?
C10 N3 Cu 124.2(3) . . ?
C14 N3 Cu 118.0(4) . . ?
C15 N4 C11 126.1(4) . . ?
C15 N4 H4A 117.0 . . ?
C11 N4 H4A 117.0 . . ?
N1 C1 C2 124.3(6) . . ?
N1 C1 H1A 117.9 . . ?
C2 C1 H1A 117.9 . . ?
C3 C2 C1 118.5(6) . . ?
C3 C2 N2 124.5(6) . . ?
C1 C2 N2 116.9(6) . . ?
C2 C3 C4 118.8(6) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C3 C4 C5 120.1(6) . . ?
C3 C4 H4B 120.0 . . ?
C5 C4 H4B 120.0 . . ?
N1 C5 C4 121.6(6) . . ?
N1 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
O1 C6 N2 116.8(10) . . ?
O1 C6 C7 122.7(9) . . ?
N2 C6 C7 120.4(9) . . ?
C6 C7 C8 114.2(9) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 114.2(7) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C9 C9 C8 125.1(16) 2 . ?
C9 C9 H9A 106.0 2 . ?
C8 C9 H9A 106.0 . . ?
C9 C9 H9B 106.0 2 . ?
C8 C9 H9B 106.0 . . ?
H9A C9 H9B 106.3 . . ?
O1' C6' C7' 127(3) . . ?
O1' C6' N2 132(2) . . ?
C7' C6' N2 101(2) . . ?
C6' C7' C8' 116(2) . . ?
C6' C7' H7'A 108.3 . . ?
C8' C7' H7'A 108.3 . . ?
C6' C7' H7'B 108.3 . . ?
C8' C7' H7'B 108.3 . . ?
H7'A C7' H7'B 107.4 . . ?
C9' C8' C7' 114(2) . . ?
C9' C8' H8'A 108.9 . . ?
C7' C8' H8'A 108.9 . . ?
C9' C8' H8'B 108.9 . . ?
C7' C8' H8'B 108.9 . . ?
H8'A C8' H8'B 107.7 . . ?
N3 C10 C11 122.7(5) . . ?
N3 C10 H10A 118.6 . . ?
C11 C10 H10A 118.6 . . ?
C10 C11 N4 118.2(4) . . ?
C10 C11 C12 118.9(5) . . ?
N4 C11 C12 122.8(5) . . ?
C13 C12 C11 118.0(6) . . ?
C13 C12 H12A 121.0 . . ?
C11 C12 H12A 121.0 . . ?
C12 C13 C14 120.4(5) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
N3 C14 C13 122.2(5) . . ?
N3 C14 H14A 118.9 . . ?
C13 C14 H14A 118.9 . . ?
O2 C15 N4 122.4(5) . . ?
O2 C15 C16 122.6(5) . . ?
N4 C15 C16 115.0(5) . . ?
C15 C16 C17 112.2(6) . . ?
C15 C16 C17' 112.8(7) . . ?
C17 C16 C17' 24.2(6) . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C17' C16 H16A 87.0 . . ?
C15 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C17' C16 H16B 127.3 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C16 113.7(8) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C18 111.2(11) . 2_667 ?
C17 C18 H18A 109.4 . . ?
C18 C18 H18A 109.4 2_667 . ?
C17 C18 H18B 109.4 . . ?
C18 C18 H18B 109.4 2_667 . ?
H18A C18 H18B 108.0 . . ?
C18' C17' C16 113.3(10) . . ?
C18' C17' H17C 108.9 . . ?
C16 C17' H17C 108.9 . . ?
C18' C17' H17D 108.9 . . ?
C16 C17' H17D 108.9 . . ?
H17C C17' H17D 107.7 . . ?
C17' C18' C18' 108.9(12) . 2_667 ?
C17' C18' H18C 109.9 . . ?
C18' C18' H18C 109.9 2_667 . ?
C17' C18' H18D 109.9 . . ?
C18' C18' H18D 109.9 2_667 . ?
H18C C18' H18D 108.3 . . ?
O4 C19 O3 124.1(4) . . ?
O4 C19 C20 120.3(4) . . ?
O3 C19 C20 115.6(4) . . ?
C21 C20 C19 113.2(4) . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.8 . . ?
C26 C21 C22 119.0(5) . . ?
C26 C21 C20 121.1(4) . . ?
C22 C21 C20 119.9(4) . . ?
C23 C22 C21 121.3(5) . . ?
C23 C22 H22A 119.3 . . ?
C21 C22 H22A 119.3 . . ?
C24 C23 C22 120.0(5) . . ?
C24 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C25 C24 C23 119.2(5) . . ?
C25 C24 H24A 120.4 . . ?
C23 C24 H24A 120.4 . . ?
C24 C25 C26 122.4(5) . . ?
C24 C25 H25A 118.8 . . ?
C26 C25 H25A 118.8 . . ?
C25 C26 C21 118.0(4) . . ?
C25 C26 C27 120.0(4) . . ?
C21 C26 C27 122.0(4) . . ?
C26 C27 C28 115.3(4) . . ?
C26 C27 H27A 108.5 . . ?
C28 C27 H27A 108.5 . . ?
C26 C27 H27B 108.5 . . ?
C28 C27 H27B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
O5 C28 O6 125.8(5) . . ?
O5 C28 C27 118.2(4) . . ?
O6 C28 C27 116.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.202
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.103
_database_code_depnum_ccdc_archive 'CCDC 1014134'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H34 Cu N4 O8'
_chemical_formula_weight         618.13

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   C2/c

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

_cell_length_a                   29.5458(9)
_cell_length_b                   6.3519(2)
_cell_length_c                   18.5588(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.320(2)
_cell_angle_gamma                90.00
_cell_volume                     2841.88(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2304
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      23.27

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1292
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8524
_exptl_absorpt_correction_T_max  0.9599
_exptl_absorpt_process_details   '(XSCANS; Siemens, 1995)'

_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11290
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_av_sigmaI/netI    0.0742
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2799
_reflns_number_gt                1750
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'XSCANS (Siemens, 1995)'
_computing_cell_refinement       'XSCANS (Siemens, 1995)'
_computing_data_reduction        'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.1051P)²+0.7142P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2799
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1864
_refine_ls_wR_factor_gt          0.1577
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_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
Cu Cu 0.2500 0.2500 0.5000 0.0370(3) Uani 1 2 d S . .
O1 O 0.3910(2) 0.8971(8) 0.3768(3) 0.0943(17) Uani 1 1 d . . .
O2 O 0.18136(14) 0.1796(6) 0.3865(2) 0.0486(9) Uani 1 1 d . . .
O3 O 0.15973(16) 0.4796(7) 0.4155(3) 0.0648(11) Uani 1 1 d . . .
N1 N 0.27911(15) 0.3881(6) 0.4369(3) 0.0386(9) Uani 1 1 d . . .
N2 N 0.36195(16) 0.8431(7) 0.4633(3) 0.0443(10) Uani 1 1 d . . .
H2A H 0.3625 0.8950 0.5066 0.053 Uiso 1 1 calc R . .
C1 C 0.2713(2) 0.2954(8) 0.3667(3) 0.0478(13) Uani 1 1 d . . .
H1A H 0.2509 0.1711 0.3462 0.057 Uiso 1 1 calc R . .
C2 C 0.2921(2) 0.3759(9) 0.3233(3) 0.0520(14) Uani 1 1 d . . .
H2B H 0.2858 0.3077 0.2739 0.062 Uiso 1 1 calc R . .
C3 C 0.32248(19) 0.5584(8) 0.3532(3) 0.0438(12) Uani 1 1 d . . .
H3A H 0.3371 0.6144 0.3244 0.053 Uiso 1 1 calc R . .
C4 C 0.33108(17) 0.6573(8) 0.4254(3) 0.0361(10) Uani 1 1 d . . .
C5 C 0.30867(18) 0.5659(8) 0.4657(3) 0.0384(11) Uani 1 1 d . . .
H5A H 0.3144 0.6312 0.5152 0.046 Uiso 1 1 calc R . .
C6 C 0.3910(2) 0.9491(8) 0.4390(4) 0.0474(13) Uani 1 1 d . . .
C7 C 0.4237(2) 1.1349(8) 0.4956(3) 0.0467(13) Uani 1 1 d . . .
H7A H 0.4520 1.0859 0.5548 0.056 Uiso 1 1 calc R . .
H7B H 0.3992 1.2284 0.4994 0.056 Uiso 1 1 calc R . .
C8 C 0.4515(2) 1.2579(8) 0.4605(4) 0.0516(13) Uani 1 1 d . . .
H8A H 0.4748 1.1628 0.4546 0.062 Uiso 1 1 calc R . .
H8B H 0.4230 1.3107 0.4020 0.062 Uiso 1 1 calc R . .
C9 C 0.4861(2) 1.4404(9) 0.5181(4) 0.0532(14) Uani 1 1 d . . .
H9A H 0.5145 1.3883 0.5767 0.064 Uiso 1 1 calc R . .
H9B H 0.4628 1.5368 0.5235 0.064 Uiso 1 1 calc R . .
C10 C 0.1475(2) 0.3289(12) 0.3670(4) 0.0542(15) Uani 1 1 d . . .
C11 C 0.0931(2) 0.3072(18) 0.2773(4) 0.114(4) Uani 1 1 d . A .
H11A H 0.0986 0.3529 0.2330 0.137 Uiso 1 1 calc R . .
H11B H 0.0833 0.1592 0.2668 0.137 Uiso 1 1 calc R . .
C12 C 0.0458(2) 0.4253(15) 0.2640(5) 0.085(2) Uani 1 1 d . . .
C13 C 0.0000 0.3250(14) 0.2500 0.057(2) Uani 1 2 d S . .
H13A H 0.0000 0.1786 0.2500 0.068 Uiso 1 2 calc SR . .
C14 C 0.0451(6) 0.607(3) 0.2313(10) 0.084(4) Uani 0.50 1 d P A 1
H14A H 0.0732 0.6481 0.2235 0.100 Uiso 0.50 1 d PR A 1
C14' C 0.0464(5) 0.660(2) 0.2951(9) 0.070(4) Uani 0.50 1 d P . 2
H14B H 0.0786 0.7449 0.3156 0.084 Uiso 0.50 1 d PR . 2
C15 C -0.0027(6) 0.745(2) 0.2062(9) 0.086(4) Uani 0.50 1 d P . .
H15A H -0.0033 0.8908 0.1916 0.104 Uiso 0.50 1 d PR A .
O4 O 0.1850(7) -0.205(2) 0.3212(9) 0.387(9) Uani 1 1 d . . .
H4C H 0.1845 -0.0863 0.3418 0.464 Uiso 1 1 d R . .
H4D H 0.1906 -0.3017 0.3572 0.464 Uiso 1 1 d R . .


_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
Cu O2 1.952(3) 7_556 ?
Cu O2 1.952(3) . ?
Cu N1 2.011(4) . ?
Cu N1 2.011(4) 7_556 ?
O1 C6 1.202(6) . ?
O2 C10 1.270(7) . ?
O3 C10 1.218(7) . ?
N1 C1 1.324(6) . ?
N1 C5 1.336(6) . ?
N2 C6 1.356(6) . ?
N2 C4 1.406(6) . ?
N2 H2A 0.8600 . ?
C1 C2 1.364(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.371(7) . ?
C2 H2B 0.9300 . ?
C3 C4 1.364(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.502(7) . ?
C7 C8 1.526(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.507(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C9 1.528(9) 5_686 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.510(7) . ?
C11 C12 1.475(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C14 1.299(17) . ?
C12 C13 1.379(8) . ?
C12 C14' 1.595(17) . ?
C13 C12 1.379(8) 2 ?
C13 H13A 0.9300 . ?
C14 C15 1.49(2) . ?
C14 H14A 0.9599 . ?
C14' C15 1.386(19) 2 ?
C14' C15 1.535(18) . ?
C14' H14B 0.9602 . ?
C15 C14' 1.386(19) 2 ?
C15 C15 1.54(3) 2 ?
C15 H15A 0.9600 . ?
O4 H4C 0.8500 . ?
O4 H4D 0.8501 . ?

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
O2 Cu O2 179.997(1) 7_556 . ?
O2 Cu N1 90.07(15) 7_556 . ?
O2 Cu N1 89.94(14) . . ?
O2 Cu N1 89.93(14) 7_556 7_556 ?
O2 Cu N1 90.06(15) . 7_556 ?
N1 Cu N1 179.998(1) . 7_556 ?
C10 O2 Cu 107.0(4) . . ?
C1 N1 C5 118.1(4) . . ?
C1 N1 Cu 119.3(3) . . ?
C5 N1 Cu 122.4(3) . . ?
C6 N2 C4 127.0(4) . . ?
C6 N2 H2A 116.5 . . ?
C4 N2 H2A 116.5 . . ?
N1 C1 C2 122.2(5) . . ?
N1 C1 H1A 118.9 . . ?
C2 C1 H1A 118.9 . . ?
C1 C2 C3 119.4(5) . . ?
C1 C2 H2B 120.3 . . ?
C3 C2 H2B 120.3 . . ?
C4 C3 C2 119.6(5) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 117.6(4) . . ?
C3 C4 N2 125.3(4) . . ?
C5 C4 N2 117.1(4) . . ?
N1 C5 C4 123.1(4) . . ?
N1 C5 H5A 118.5 . . ?
C4 C5 H5A 118.5 . . ?
O1 C6 N2 122.3(5) . . ?
O1 C6 C7 122.0(4) . . ?
N2 C6 C7 115.7(5) . . ?
C6 C7 C8 113.0(4) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 113.8(4) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C9 112.7(6) . 5_686 ?
C8 C9 H9A 109.0 . . ?
C9 C9 H9A 109.0 5_686 . ?
C8 C9 H9B 109.0 . . ?
C9 C9 H9B 109.0 5_686 . ?
H9A C9 H9B 107.8 . . ?
O3 C10 O2 121.8(5) . . ?
O3 C10 C11 124.0(7) . . ?
O2 C10 C11 114.1(6) . . ?
C12 C11 C10 116.0(6) . . ?
C12 C11 H11A 108.3 . . ?
C10 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C14 C12 C13 124.9(9) . . ?
C14 C12 C11 106.8(9) . . ?
C13 C12 C11 121.9(8) . . ?
C14 C12 C14' 48.1(8) . . ?
C13 C12 C14' 107.7(8) . . ?
C11 C12 C14' 127.2(8) . . ?
C12 C13 C12 124.9(10) . 2 ?
C12 C13 H13A 117.5 . . ?
C12 C13 H13A 117.5 2 . ?
C12 C14 C15 115.3(13) . . ?
C12 C14 H14A 121.9 . . ?
C15 C14 H14A 122.8 . . ?
C12 C14 H14B 101.6 . . ?
C15 C14 H14B 85.4 . . ?
H14A C14 H14B 84.0 . . ?
C15 C14' C15 63.3(13) 2 . ?
C15 C14' C12 123.0(12) 2 . ?
C15 C14' C12 97.8(10) . . ?
C15 C14' H14B 119.0 2 . ?
C15 C14' H14B 109.3 . . ?
C12 C14' H14B 118.0 . . ?
C14' C15 C14 118.6(14) 2 . ?
C14' C15 C14' 99.9(13) 2 . ?
C14 C15 C14' 47.1(8) . . ?
C14' C15 C15 63.1(11) 2 2 ?
C14 C15 C15 99.7(12) . 2 ?
C14' C15 C15 53.7(9) . 2 ?
C14' C15 H15A 120.6 2 . ?
C14 C15 H15A 120.8 . . ?
C14' C15 H15A 119.7 . . ?
C15 C15 H15A 105.9 2 . ?
H4C O4 H4D 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.824
_refine_diff_density_rms         0.087
_database_code_depnum_ccdc_archive 'CCDC 1014135'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H34 Cu N4 O8'
_chemical_formula_weight         618.13

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           Orthorhombic
_symmetry_space_group_name_H-M   Pmna

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

_cell_length_a                   15.8723(8)
_cell_length_b                   12.1103(6)
_cell_length_c                   14.8539(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2855.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4496
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      24.74

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1292
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7907
_exptl_absorpt_correction_T_max  0.9601
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'

_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22135
_diffrn_reflns_av_R_equivalents  0.1033
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2924
_reflns_number_gt                1844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1126P)²+5.7921P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2924
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0750
_refine_ls_wR_factor_ref         0.2242
_refine_ls_wR_factor_gt          0.1865
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_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
Cu Cu 0.5000 0.46051(6) 0.39338(5) 0.0303(2) Uani 1 2 d S . .
O1 O 0.7223(3) 0.7701(3) 0.3782(4) 0.0762(16) Uani 1 1 d . . .
O2 O 0.5000 0.6048(3) 0.4546(3) 0.0344(11) Uani 1 2 d S . .
O3 O 0.5000 0.6952(4) 0.3249(4) 0.0497(14) Uani 1 2 d S . .
O4 O 0.5000 1.3146(4) 0.3381(4) 0.0415(13) Uani 1 2 d S . .
O5 O 0.5000 1.3709(4) 0.1958(4) 0.0558(16) Uani 1 2 d S . .
O6 O 1.0000 0.5870(4) 0.3306(3) 0.0442(13) Uani 1 2 d S . .
H6C H 1.0000 0.5207 0.3118 0.053 Uiso 1 2 d SR . .
H6D H 1.0000 0.6301 0.2854 0.053 Uiso 1 2 d SR . .
O7 O 1.0000 0.681(2) 0.5148(14) 0.381(15) Uani 1 2 d S . .
H7E H 1.0000 0.6534 0.5674 0.457 Uiso 1 2 d SR . .
H7F H 1.0000 0.6290 0.4766 0.457 Uiso 1 2 d SR . .
N1 N 0.6287(3) 0.4559(3) 0.3868(3) 0.0360(10) Uani 1 1 d . . .
N2 N 0.8162(3) 0.6313(4) 0.3596(3) 0.0517(13) Uani 1 1 d . . .
H2A H 0.8685 0.6173 0.3498 0.062 Uiso 1 1 calc R . .
C1 C 0.6764(3) 0.5450(4) 0.3734(3) 0.0390(13) Uani 1 1 d . . .
H1A H 0.6504 0.6131 0.3658 0.047 Uiso 1 1 calc R . .
C2 C 0.7638(4) 0.5392(4) 0.3705(4) 0.0440(14) Uani 1 1 d . . .
C3 C 0.8024(4) 0.4385(5) 0.3807(4) 0.0538(17) Uani 1 1 d . . .
H3A H 0.8608 0.4322 0.3787 0.065 Uiso 1 1 calc R . .
C4 C 0.7523(4) 0.3468(5) 0.3940(5) 0.0619(18) Uani 1 1 d . . .
H4A H 0.7768 0.2774 0.4006 0.074 Uiso 1 1 calc R . .
C5 C 0.6668(4) 0.3582(5) 0.3973(4) 0.0501(15) Uani 1 1 d . . .
H5A H 0.6338 0.2959 0.4072 0.060 Uiso 1 1 calc R . .
C6 C 0.7951(4) 0.7395(5) 0.3623(4) 0.0508(15) Uani 1 1 d . . .
C7 C 0.8658(4) 0.8180(5) 0.3452(5) 0.0577(17) Uani 1 1 d . . .
H7A H 0.8747 0.8230 0.2807 0.069 Uiso 1 1 calc R . .
H7B H 0.9167 0.7878 0.3717 0.069 Uiso 1 1 calc R . .
C8 C 0.8528(5) 0.9331(5) 0.3816(4) 0.0619(19) Uani 1 1 d . . .
H8A H 0.8974 0.9802 0.3589 0.074 Uiso 1 1 calc R . .
H8B H 0.7999 0.9614 0.3586 0.074 Uiso 1 1 calc R . .
C9 C 0.8516(5) 0.9409(5) 0.4826(5) 0.070(2) Uani 1 1 d . . .
H9A H 0.9005 0.9028 0.5064 0.083 Uiso 1 1 calc R . .
H9B H 0.8018 0.9034 0.5050 0.083 Uiso 1 1 calc R . .
C10 C 0.5000 0.6947(6) 0.4073(5) 0.0369(18) Uani 1 2 d S . .
C11 C 0.5000 0.8028(6) 0.4592(6) 0.063(3) Uani 1 2 d S . .
H11A H 0.5489 0.8042 0.4973 0.076 Uiso 1 1 d R . .
C12 C 0.5000 0.9057(6) 0.4038(5) 0.046(2) Uani 1 2 d S . .
C13 C 0.5736(5) 0.9543(5) 0.3774(4) 0.0604(18) Uani 1 1 d . . .
H13A H 0.6246 0.9248 0.3968 0.072 Uiso 1 1 calc R . .
C14 C 0.5740(5) 1.0462(5) 0.3225(5) 0.072(2) Uani 1 1 d . . .
H14A H 0.6251 1.0784 0.3065 0.086 Uiso 1 1 calc R . .
C15 C 0.5000 1.0908(7) 0.2911(6) 0.068(3) Uani 1 2 d S . .
C16 C 0.5000 1.1792(6) 0.2241(6) 0.050(2) Uani 1 2 d S . .
H16A H 0.5489 1.1688 0.1870 0.050(16) Uiso 1 1 d R . .
C17 C 0.5000 1.2995(6) 0.2547(5) 0.0407(18) Uani 1 2 d S . .


_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
Cu O4 1.949(5) 1_545 ?
Cu O2 1.970(4) . ?
Cu N1 2.046(4) 8_655 ?
Cu N1 2.046(4) . ?
Cu O2 2.393(5) 5_666 ?
O1 C6 1.237(7) . ?
O2 C10 1.295(8) . ?
O2 Cu 2.393(5) 5_666 ?
O3 C10 1.224(9) . ?
O4 C17 1.252(9) . ?
O4 Cu 1.949(5) 1_565 ?
O5 C17 1.230(9) . ?
O6 H6C 0.8500 . ?
O6 H6D 0.8501 . ?
O7 H7E 0.8500 . ?
O7 H7F 0.8500 . ?
N1 C1 1.334(6) . ?
N1 C5 1.337(7) . ?
N2 C6 1.352(7) . ?
N2 C2 1.401(7) . ?
N2 H2A 0.8600 . ?
C1 C2 1.389(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.373(7) . ?
C3 C4 1.379(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.366(8) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.492(8) . ?
C7 C8 1.509(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.503(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C9 1.523(11) 4_576 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.520(10) . ?
C11 C12 1.493(10) . ?
C11 H11A 0.9601 . ?
C12 C13 1.366(8) . ?
C12 C13 1.366(8) 8_655 ?
C13 C14 1.379(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.375(9) . ?
C14 H14A 0.9300 . ?
C15 C14 1.375(9) 8_655 ?
C15 C16 1.462(11) . ?
C16 C17 1.526(10) . ?
C16 H16A 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
O4 Cu O2 177.4(2) 1_545 . ?
O4 Cu N1 87.42(11) 1_545 8_655 ?
O2 Cu N1 92.65(11) . 8_655 ?
O4 Cu N1 87.42(11) 1_545 . ?
O2 Cu N1 92.65(11) . . ?
N1 Cu N1 173.7(2) 8_655 . ?
O4 Cu O2 95.62(19) 1_545 5_666 ?
O2 Cu O2 81.83(17) . 5_666 ?
N1 Cu O2 92.04(11) 8_655 5_666 ?
N1 Cu O2 92.04(11) . 5_666 ?
C10 O2 Cu 119.7(5) . . ?
C10 O2 Cu 142.2(4) . 5_666 ?
Cu O2 Cu 98.17(17) . 5_666 ?
C17 O4 Cu 123.4(5) . 1_565 ?
H6C O6 H6D 108.7 . . ?
H7E O7 H7F 108.5 . . ?
C1 N1 C5 118.4(5) . . ?
C1 N1 Cu 123.5(3) . . ?
C5 N1 Cu 118.0(4) . . ?
C6 N2 C2 128.4(5) . . ?
C6 N2 H2A 115.8 . . ?
C2 N2 H2A 115.8 . . ?
N1 C1 C2 122.1(5) . . ?
N1 C1 H1A 119.0 . . ?
C2 C1 H1A 119.0 . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 N2 117.1(5) . . ?
C1 C2 N2 123.8(5) . . ?
C2 C3 C4 118.3(5) . . ?
C2 C3 H3A 120.9 . . ?
C4 C3 H3A 120.9 . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
N1 C5 C4 122.3(5) . . ?
N1 C5 H5A 118.8 . . ?
C4 C5 H5A 118.8 . . ?
O1 C6 N2 121.8(6) . . ?
O1 C6 C7 122.9(6) . . ?
N2 C6 C7 115.3(5) . . ?
C6 C7 C8 115.2(5) . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C7 114.7(5) . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C9 113.4(7) . 4_576 ?
C8 C9 H9A 108.9 . . ?
C9 C9 H9A 108.9 4_576 . ?
C8 C9 H9B 108.9 . . ?
C9 C9 H9B 108.9 4_576 . ?
H9A C9 H9B 107.7 . . ?
O3 C10 O2 123.2(7) . . ?
O3 C10 C11 120.2(6) . . ?
O2 C10 C11 116.7(7) . . ?
C12 C11 C10 116.1(7) . . ?
C12 C11 H11A 108.1 . . ?
C10 C11 H11A 108.3 . . ?
C13 C12 C13 117.6(8) . 8_655 ?
C13 C12 C11 121.2(4) . . ?
C13 C12 C11 121.2(4) 8_655 . ?
C12 C13 C14 121.4(7) . . ?
C12 C13 H13A 119.3 . . ?
C14 C13 H13A 119.3 . . ?
C15 C14 C13 120.9(7) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C14 C15 C14 117.5(8) . 8_655 ?
C14 C15 C16 121.2(4) . . ?
C14 C15 C16 121.2(4) 8_655 . ?
C15 C16 C17 119.7(7) . . ?
C15 C16 H16A 107.2 . . ?
C17 C16 H16A 107.2 . . ?
O5 C17 O4 126.9(7) . . ?
O5 C17 C16 117.3(7) . . ?
O4 C17 C16 115.8(7) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.450
_refine_diff_density_min         -2.026
_refine_diff_density_rms         0.133



#===END
_database_code_depnum_ccdc_archive 'CCDC 1014136'
