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

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#
#                 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.
#
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#  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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#  from this site to visualise CIF-encoded structures and 
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data_MOF-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H15 Cu O5, 4(O)'
_chemical_formula_sum            'C27 H15 Cu O9'
_chemical_formula_weight         546.94

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'
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   'I m a 2'
_symmetry_space_group_name_Hall  'I 2 -2a'

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

_cell_length_a                   37.755(19)
_cell_length_b                   13.781(7)
_cell_length_c                   29.867(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     15540(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'block shape'
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2224.0
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_T_max  0.709
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90(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 scan'
_diffrn_detector_area_resol_mean 0.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36996
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_av_sigmaI/netI    0.4911
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         30.58
_reflns_number_total             19595
_reflns_number_gt                3644
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^ > 2\s(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.
;

_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^)+(0.2000P)^2^+0.0000P] 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    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   0.00
_refine_ls_number_reflns         19595
_refine_ls_number_parameters     338
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.2470
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.2558
_refine_ls_wR_factor_gt          0.1906
_refine_ls_goodness_of_fit_ref   0.453
_refine_ls_restrained_S_all      0.463
_refine_ls_shift/su_max          9.801
_refine_ls_shift/su_mean         0.898

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 0.980343(15) 0.42172(5) 0.89848(5) 0.0559(2) Uani 1 1 d . . .
C28 C 0.9607(2) 0.5672(7) 0.9604(2) 0.030(2) Uani 1 1 d . . .
O1 O 0.95197(17) 0.4914(6) 0.94573(18) 0.070(2) Uani 1 1 d . . .
O2 O 0.95468(15) 0.4880(5) 0.85330(16) 0.0526(19) Uani 1 1 d . . .
C11 C 1.0903(3) 0.4394(9) 0.7860(3) 0.078(4) Uani 1 1 d . . .
H11 H 1.0981 0.4974 0.7984 0.093 Uiso 1 1 calc R . .
C6 C 1.0598(3) 0.3888(9) 0.7996(3) 0.077(4) Uani 1 1 d DU . .
C21 C 0.9408(3) 0.6091(9) 0.9985(3) 0.064(3) Uani 1 1 d . . .
C1 C 0.9098(3) 0.5632(8) 1.0116(3) 0.066(4) Uani 1 1 d . . .
H1 H 0.9021 0.5111 0.9944 0.079 Uiso 1 1 calc R . .
C8 C 1.0681(3) 0.2661(9) 0.7421(3) 0.106(4) Uani 1 1 d . . .
H8 H 1.0577 0.2172 0.7253 0.127 Uiso 1 1 calc R . .
C7 C 1.0494(2) 0.3008(8) 0.7795(3) 0.054(3) Uani 1 1 d . . .
H7 H 1.0303 0.2660 0.7909 0.065 Uiso 1 1 calc R . .
C15 C 1.1556(3) 0.2167(8) 0.6110(3) 0.075(4) Uani 1 1 d . . .
H15 H 1.1677 0.1985 0.5852 0.090 Uiso 1 1 calc R . .
C10 C 1.1071(3) 0.3892(8) 0.7510(3) 0.087(3) Uani 1 1 d U . .
H10 H 1.1266 0.4228 0.7400 0.105 Uiso 1 1 calc R . .
C18 C 1.21273(17) 0.2447(11) 0.6506(4) 0.089(3) Uani 1 1 d . . .
C4 C 0.9338(3) 0.7242(7) 1.0584(3) 0.058(3) Uani 1 1 d U . .
H4 H 0.9395 0.7824 1.0724 0.070 Uiso 1 1 calc R . .
C27 C 0.8888(3) 0.5896(8) 1.0495(3) 0.071(3) Uani 1 1 d U . .
H27 H 0.8679 0.5589 1.0580 0.085 Uiso 1 1 calc R . .
C33 C 1.2269(3) 0.4959(6) 0.6182(5) 0.310(6) Uani 1 1 d DU . .
H33 H 1.2124 0.5496 0.6227 0.372 Uiso 1 1 calc R . .
C12 C 1.1176(2) 0.2766(6) 0.6880(2) 0.045(2) Uani 1 1 d U . .
C14 C 1.1184(3) 0.1992(9) 0.6147(4) 0.091(4) Uani 1 1 d U . .
C20 C 1.2306(2) 0.3092(5) 0.6262(3) 0.079(3) Uani 1 1 d D . .
C19 C 1.2263(3) 0.1579(8) 0.6775(4) 0.144(4) Uani 1 1 d DU . .
C30 C 1.0345(4) 0.4225(10) 0.8388(4) 0.094(4) Uani 1 1 d DU . .
C32 C 1.2136(5) 0.3851(12) 0.6089(6) 0.236(8) Uani 1 1 d U . .
H32 H 1.1937 0.3747 0.5911 0.283 Uiso 1 1 calc R . .
O1W O 0.9496(4) 0.2648(10) 1.0302(5) 0.351(6) Uani 1 1 d U . .
O2W O 1.1164(4) 0.5101(12) 0.5902(5) 0.408(7) Uani 1 1 d U . .
O3W O 1.0000 0.5000 1.1316(6) 0.340(9) Uani 1 2 d SU . .
O4W O 1.2500 -0.0131(16) 0.5875(6) 0.345(10) Uani 1 2 d SU . .
O5W O 1.0333(4) 0.1181(13) 0.9081(8) 0.447(10) Uani 1 1 d U . .
C13 C 1.09934(15) 0.2387(9) 0.6511(3) 0.072(2) Uani 1 1 d . . .
H13 H 1.0747 0.2395 0.6506 0.087 Uiso 1 1 calc R . .
C9 C 1.1017(2) 0.3000(8) 0.7283(3) 0.074(3) Uani 1 1 d . . .
C17 C 1.1534(2) 0.2866(8) 0.6840(3) 0.081(4) Uani 1 1 d . . .
H17 H 1.1656 0.3125 0.7082 0.097 Uiso 1 1 calc R . .
C3 C 0.9044(2) 0.6699(7) 1.0725(3) 0.050(2) Uani 1 1 d . . .
C5 C 0.9543(3) 0.6896(9) 1.0231(3) 0.084(4) Uani 1 1 d . . .
H5 H 0.9760 0.7178 1.0159 0.101 Uiso 1 1 calc R . .
C16 C 1.17352(15) 0.2604(11) 0.6455(4) 0.076(3) Uani 1 1 d . . .
O4 O 0.94594(11) 0.2956(3) 0.8958(3) 0.0908(14) Uani 1 1 d . . .
O5 O 1.01214(19) 0.3693(6) 0.85287(18) 0.070(2) Uani 1 1 d . . .
C23 C 1.2130(3) 0.1059(9) 0.7063(4) 0.127(4) Uani 1 1 d DU . .
H23 H 1.1888 0.1109 0.7115 0.153 Uiso 1 1 calc R . .
O6 O 0.98592(17) 0.6189(5) 0.94565(18) 0.062(2) Uani 1 1 d . . .
C31 C 1.2307(2) 0.0458(9) 0.7293(3) 0.146(5) Uani 1 1 d D . .
H31 H 1.2187 0.0004 0.7466 0.176 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 0.0489(4) 0.0948(5) 0.0240(3) 0.0007(9) -0.0017(8) 0.0111(4)
C28 0.024(4) 0.051(6) 0.014(3) -0.005(3) 0.001(3) 0.017(4)
O1 0.058(5) 0.117(7) 0.036(4) -0.001(4) 0.016(3) 0.023(4)
O2 0.034(4) 0.087(6) 0.037(4) 0.015(3) -0.012(3) -0.002(3)
C11 0.033(6) 0.134(11) 0.066(6) -0.049(7) 0.021(5) -0.019(6)
C6 0.078(7) 0.101(8) 0.052(5) -0.008(5) -0.003(6) 0.052(6)
C21 0.054(6) 0.126(10) 0.013(4) -0.012(5) 0.003(5) -0.015(6)
C1 0.062(8) 0.117(10) 0.018(5) -0.011(5) -0.010(5) 0.012(7)
C8 0.057(7) 0.192(13) 0.067(7) -0.021(7) -0.028(6) -0.006(8)
C7 0.027(4) 0.102(8) 0.034(4) -0.021(5) -0.007(4) 0.009(5)
C15 0.041(6) 0.155(12) 0.029(4) -0.034(6) 0.006(5) -0.009(7)
C10 0.040(5) 0.159(7) 0.063(5) -0.008(5) 0.011(4) -0.019(4)
C18 0.066(5) 0.164(8) 0.036(3) -0.017(4) 0.007(6) -0.078(8)
C4 0.057(6) 0.078(6) 0.039(5) -0.030(4) 0.017(4) 0.006(5)
C27 0.049(6) 0.119(7) 0.044(5) -0.044(5) 0.006(5) -0.013(5)
C33 0.212(9) 0.321(10) 0.397(10) -0.018(8) -0.028(8) 0.065(8)
C12 0.029(4) 0.072(5) 0.035(3) -0.034(3) 0.006(3) 0.005(3)
C14 0.078(7) 0.140(8) 0.054(5) 0.001(5) 0.012(5) 0.021(6)
C20 0.041(5) 0.099(7) 0.097(6) 0.008(5) -0.045(4) 0.030(4)
C19 0.083(7) 0.157(8) 0.192(8) 0.044(7) -0.053(6) 0.001(6)
C30 0.104(8) 0.133(9) 0.046(6) -0.017(6) -0.014(6) 0.035(7)
C32 0.208(11) 0.208(11) 0.292(11) 0.061(9) -0.007(9) -0.013(8)
O1W 0.331(8) 0.354(8) 0.367(8) 0.000(5) 0.017(5) -0.015(5)
O2W 0.393(9) 0.401(9) 0.429(8) 0.013(5) -0.026(5) 0.005(5)
O3W 0.333(10) 0.339(10) 0.346(10) 0.000 0.000 -0.007(5)
O4W 0.359(11) 0.338(11) 0.338(11) -0.014(5) 0.000 0.000
O5W 0.450(10) 0.435(10) 0.456(11) -0.004(5) -0.005(5) -0.002(5)
C13 0.040(3) 0.143(7) 0.034(3) -0.032(4) -0.010(5) -0.015(7)
C9 0.054(6) 0.107(9) 0.060(6) -0.043(6) 0.026(5) -0.018(6)
C17 0.027(6) 0.132(11) 0.083(7) -0.060(7) -0.016(6) -0.016(6)
C3 0.043(5) 0.069(6) 0.037(4) -0.030(4) -0.021(4) 0.042(4)
C5 0.078(8) 0.119(11) 0.056(6) -0.014(6) 0.006(6) 0.014(7)
C16 0.040(3) 0.146(8) 0.041(4) -0.034(4) -0.021(5) 0.024(7)
O4 0.100(3) 0.103(3) 0.069(3) 0.007(5) 0.002(6) -0.022(3)
O5 0.068(5) 0.109(6) 0.034(4) -0.026(4) 0.027(4) -0.030(4)
C23 0.095(7) 0.167(8) 0.120(6) 0.043(6) 0.040(6) -0.042(6)
O6 0.062(5) 0.093(6) 0.032(4) -0.012(3) -0.003(3) 0.025(4)
C31 0.087(7) 0.206(13) 0.146(9) 0.101(9) -0.017(6) -0.036(7)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 1.896(6) . ?
Cu1 O5 1.954(6) . ?
Cu1 O6 1.980(6) 2_765 ?
Cu1 O1 2.015(6) . ?
Cu1 O4 2.171(4) . ?
Cu1 Cu1 2.6188(17) 2_765 ?
C28 O1 1.180(10) . ?
C28 O6 1.268(11) . ?
C28 C21 1.480(10) . ?
O2 C30 1.370(14) 2_765 ?
C11 C6 1.406(14) . ?
C11 C10 1.406(12) . ?
C6 C7 1.408(13) . ?
C6 C30 1.579(8) . ?
C21 C5 1.425(13) . ?
C21 C1 1.386(13) . ?
C1 C27 1.432(12) . ?
C8 C9 1.411(13) . ?
C8 C7 1.406(11) . ?
C15 C16 1.372(12) . ?
C15 C14 1.429(13) . ?
C10 C9 1.419(12) . ?
C18 C20 1.335(12) . ?
C18 C16 1.504(9) . ?
C18 C19 1.527(14) . ?
C4 C3 1.403(12) . ?
C4 C5 1.392(11) . ?
C27 C3 1.428(12) . ?
C33 C33 1.75(2) 3_755 ?
C33 C32 1.632(17) . ?
C12 C17 1.362(11) . ?
C12 C13 1.401(10) . ?
C12 C9 1.385(10) . ?
C14 C13 1.413(12) . ?
C14 C3 1.581(13) 7_644 ?
C20 C32 1.332(17) . ?
C20 C20 1.463(16) 3_755 ?
C19 C23 1.227(10) . ?
C19 C19 1.79(2) 3_755 ?
C30 O5 1.195(14) . ?
C30 O2 1.370(14) 2_765 ?
C17 C16 1.423(12) . ?
C3 C14 1.581(13) 7_655 ?
C23 C31 1.267(12) . ?
O6 Cu1 1.980(6) 2_765 ?
C31 C31 1.459(18) 3_755 ?

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 Cu1 O5 89.8(3) . . ?
O2 Cu1 O6 166.3(3) . 2_765 ?
O5 Cu1 O6 89.79(16) . 2_765 ?
O2 Cu1 O1 89.84(15) . . ?
O5 Cu1 O1 172.2(3) . . ?
O6 Cu1 O1 88.8(2) 2_765 . ?
O2 Cu1 O4 93.1(3) . . ?
O5 Cu1 O4 92.6(3) . . ?
O6 Cu1 O4 100.6(3) 2_765 . ?
O1 Cu1 O4 95.1(3) . . ?
O2 Cu1 Cu1 83.9(2) . 2_765 ?
O5 Cu1 Cu1 87.5(2) . 2_765 ?
O6 Cu1 Cu1 82.4(2) 2_765 2_765 ?
O1 Cu1 Cu1 84.8(2) . 2_765 ?
O4 Cu1 Cu1 176.92(18) . 2_765 ?
O1 C28 O6 125.3(8) . . ?
O1 C28 C21 119.3(9) . . ?
O6 C28 C21 115.4(9) . . ?
C28 O1 Cu1 122.3(6) . . ?
C30 O2 Cu1 120.4(6) 2_765 . ?
C6 C11 C10 110.0(9) . . ?
C11 C6 C7 122.1(9) . . ?
C11 C6 C30 124.2(11) . . ?
C7 C6 C30 113.6(11) . . ?
C28 C21 C5 121.3(9) . . ?
C28 C21 C1 117.8(10) . . ?
C5 C21 C1 120.7(9) . . ?
C27 C1 C21 125.2(10) . . ?
C9 C8 C7 124.9(10) . . ?
C6 C7 C8 119.4(10) . . ?
C16 C15 C14 120.0(9) . . ?
C11 C10 C9 135.7(9) . . ?
C20 C18 C16 110.3(11) . . ?
C20 C18 C19 129.7(7) . . ?
C16 C18 C19 119.7(10) . . ?
C3 C4 C5 119.0(9) . . ?
C1 C27 C3 110.3(9) . . ?
C33 C33 C32 107.9(8) 3_755 . ?
C17 C12 C13 117.2(7) . . ?
C17 C12 C9 119.0(8) . . ?
C13 C12 C9 123.8(8) . . ?
C15 C14 C13 119.8(10) . . ?
C15 C14 C3 121.1(9) . 7_644 ?
C13 C14 C3 115.7(9) . 7_644 ?
C18 C20 C32 119.4(12) . . ?
C18 C20 C20 120.4(5) . 3_755 ?
C32 C20 C20 118.9(9) . 3_755 ?
C23 C19 C18 133.4(13) . . ?
C23 C19 C19 114.2(8) . 3_755 ?
C18 C19 C19 109.6(5) . 3_755 ?
O5 C30 O2 130.7(10) . 2_765 ?
O5 C30 C6 120.5(12) . . ?
O2 C30 C6 108.6(10) 2_765 . ?
C20 C32 C33 121.3(14) . . ?
C12 C13 C14 119.8(5) . . ?
C12 C9 C10 123.7(9) . . ?
C12 C9 C8 124.6(9) . . ?
C10 C9 C8 106.0(9) . . ?
C12 C17 C16 125.1(8) . . ?
C4 C3 C27 126.5(8) . . ?
C4 C3 C14 122.3(8) . 7_655 ?
C27 C3 C14 110.8(9) . 7_655 ?
C4 C5 C21 117.3(10) . . ?
C15 C16 C18 119.9(11) . . ?
C15 C16 C17 117.0(5) . . ?
C18 C16 C17 118.7(10) . . ?
C30 O5 Cu1 116.9(8) . . ?
C31 C23 C19 123.2(12) . . ?
C28 O6 Cu1 124.9(6) . 2_765 ?
C23 C31 C31 121.8(7) . 3_755 ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        30.58
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 939459'