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

#######################################################################
#
#                 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_hnust-2
#TrackingRef 'hnust-2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H6 Cu O5'
_chemical_formula_sum            'C15 H6 Cu O5'
_chemical_formula_weight         329.74

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           trigonal
_symmetry_space_group_name_H-M   R-3m

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'

_cell_length_a                   18.6777(3)
_cell_length_b                   18.6777(3)
_cell_length_c                   54.443(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     16448.2(7)
_cell_formula_units_Z            18
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    0.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2970
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8396
_exptl_absorpt_correction_T_max  0.8786
_exptl_absorpt_process_details   'SADABS-2007/4; (Bruker, 2007)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(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 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30329
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       67
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3940
_reflns_number_gt                2463
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.
;

_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^)+(0.1996P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3940
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0866
_refine_ls_wR_factor_ref         0.3138
_refine_ls_wR_factor_gt          0.2861
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_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
C1 C -0.0280(3) 0.2137(3) 0.18609(8) 0.0711(11) Uani 1 1 d . . .
C2 C 0.10742(17) 0.2148(3) 0.18577(9) 0.0600(13) Uani 1 2 d S . .
H2 H 0.0971 0.1942 0.1698 0.072 Uiso 1 2 calc SR . .
C3 C 0.0505(3) 0.2309(2) 0.19815(7) 0.0644(10) Uani 1 1 d . . .
C4 C 0.0639(3) 0.2562(2) 0.22256(7) 0.0633(10) Uani 1 1 d . . .
H4 H 0.0241 0.2623 0.2311 0.076 Uiso 1 1 calc R . .
C5 C 0.1361(2) 0.2722(4) 0.23423(12) 0.0703(16) Uani 1 2 d S . .
C6 C 0.1445(2) 0.2890(4) 0.26058(13) 0.0728(17) Uani 1 2 d S . .
C7 C 0.1510(2) 0.3020(4) 0.28247(15) 0.0816(19) Uani 1 2 d S . .
C8 C 0.1597(3) 0.3195(5) 0.30899(15) 0.097(2) Uani 1 2 d S . .
C9 C 0.0982(4) 0.3245(4) 0.32148(12) 0.107(2) Uani 1 1 d . . .
H9 H 0.0507 0.3155 0.3133 0.128 Uiso 0.50 1 calc PR A 1
C10 C 0.0293(7) 0.3154(7) 0.3088(2) 0.104(4) Uani 0.50 1 d P . 2
H10 H 0.0235 0.3030 0.2922 0.125 Uiso 0.50 1 calc PR . 2
C11 C -0.0308(8) 0.3249(8) 0.3211(2) 0.111(4) Uani 0.50 1 d P . 2
H11 H -0.0764 0.3198 0.3126 0.133 Uiso 0.50 1 calc PR . 2
Cu1 Cu -0.14308(2) 0.14308(2) 0.146639(11) 0.0678(4) Uani 1 2 d S . .
O1 O -0.0784(2) 0.2226(2) 0.19804(6) 0.0792(9) Uani 1 1 d . . .
O3 O -0.0379(2) 0.1855(2) 0.16432(6) 0.0856(10) Uani 1 1 d . . .
O1W O -0.10913(18) 0.10913(18) 0.11362(10) 0.1055(18) Uani 1 2 d S . .

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
C1 0.074(3) 0.078(3) 0.052(2) -0.0013(18) -0.0042(19) 0.031(2)
C2 0.062(2) 0.065(3) 0.054(3) -0.006(2) -0.0030(11) 0.0326(15)
C3 0.070(2) 0.064(2) 0.057(2) -0.0038(16) -0.0009(17) 0.0322(18)
C4 0.066(2) 0.065(2) 0.055(2) -0.0119(17) -0.0095(17) 0.0296(19)
C5 0.075(3) 0.083(4) 0.056(3) -0.021(3) -0.0107(14) 0.0415(19)
C6 0.073(3) 0.080(4) 0.067(4) -0.026(3) -0.0130(14) 0.0402(19)
C7 0.081(3) 0.084(4) 0.081(5) -0.024(4) -0.0122(18) 0.042(2)
C8 0.114(5) 0.091(5) 0.079(5) -0.019(4) -0.010(2) 0.046(2)
C9 0.095(4) 0.097(4) 0.099(4) -0.025(3) -0.013(4) 0.027(3)
C10 0.082(7) 0.092(7) 0.095(8) 0.024(6) 0.013(6) 0.012(6)
C11 0.095(7) 0.100(8) 0.096(8) -0.026(7) -0.018(6) 0.017(7)
Cu1 0.0767(5) 0.0767(5) 0.0370(5) -0.00290(14) 0.00290(14) 0.0286(4)
O1 0.0777(19) 0.083(2) 0.0578(17) -0.0092(14) -0.0014(15) 0.0261(16)
O3 0.078(2) 0.099(2) 0.0591(18) -0.0086(15) -0.0056(15) 0.0294(17)
O1W 0.101(3) 0.101(3) 0.093(3) -0.0289(17) 0.0289(17) 0.033(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
C1 O1 1.221(6) . ?
C1 O3 1.272(5) . ?
C1 C3 1.489(6) . ?
C2 C3 1.412(5) 23 ?
C2 C3 1.412(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(6) . ?
C4 C5 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C4 1.382(5) 23 ?
C5 C6 1.460(9) . ?
C6 C7 1.210(10) . ?
C7 C8 1.471(11) . ?
C8 C9 1.379(8) . ?
C8 C9 1.379(8) 23 ?
C9 C9 1.322(13) 17 ?
C9 C10 1.393(14) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(18) . ?
C10 H10 0.9300 . ?
C11 C11 1.36(2) 17 ?
C11 H11 0.9300 . ?
Cu1 O1 1.963(3) 25_455 ?
Cu1 O1 1.963(3) 10_455 ?
Cu1 O3 1.964(3) 22 ?
Cu1 O3 1.964(3) . ?
Cu1 O1W 2.106(4) . ?
Cu1 Cu1 2.6620(13) 25_455 ?
O1 Cu1 1.963(3) 25_455 ?

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 C1 O3 126.2(5) . . ?
O1 C1 C3 118.6(4) . . ?
O3 C1 C3 115.1(4) . . ?
C3 C2 C3 118.4(5) 23 . ?
C3 C2 H2 120.8 23 . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 C1 119.0(4) . . ?
C2 C3 C1 120.6(4) . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C4 120.4(5) . 23 ?
C4 C5 C6 119.1(3) . . ?
C4 C5 C6 119.1(3) 23 . ?
C7 C6 C5 179.3(9) . . ?
C6 C7 C8 179.0(8) . . ?
C9 C8 C9 120.4(9) . 23 ?
C9 C8 C7 119.7(4) . . ?
C9 C8 C7 119.7(4) 23 . ?
C9 C9 C8 119.6(4) 17 . ?
C9 C9 C10 120.4(6) 17 . ?
C8 C9 C10 119.9(8) . . ?
C9 C9 H9 120.2 17 . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 3.0 . . ?
C11 C10 C9 120.2(12) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C11 C11 C10 119.4(8) 17 . ?
C11 C11 H11 120.3 17 . ?
C10 C11 H11 120.3 . . ?
O1 Cu1 O1 86.7(2) 25_455 10_455 ?
O1 Cu1 O3 90.62(16) 25_455 22 ?
O1 Cu1 O3 167.12(14) 10_455 22 ?
O1 Cu1 O3 167.12(14) 25_455 . ?
O1 Cu1 O3 90.62(16) 10_455 . ?
O3 Cu1 O3 89.2(2) 22 . ?
O1 Cu1 O1W 94.21(16) 25_455 . ?
O1 Cu1 O1W 94.21(16) 10_455 . ?
O3 Cu1 O1W 98.56(16) 22 . ?
O3 Cu1 O1W 98.56(16) . . ?
O1 Cu1 Cu1 83.22(10) 25_455 25_455 ?
O1 Cu1 Cu1 83.21(10) 10_455 25_455 ?
O3 Cu1 Cu1 83.96(10) 22 25_455 ?
O3 Cu1 Cu1 83.95(10) . 25_455 ?
O1W Cu1 Cu1 176.44(19) . 25_455 ?
C1 O1 Cu1 124.3(3) . 25_455 ?
C1 O3 Cu1 122.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C2 C3 C4 -4.6(8) 23 . . . ?
C3 C2 C3 C1 -179.0(3) 23 . . . ?
O1 C1 C3 C4 0.2(6) . . . . ?
O3 C1 C3 C4 -175.4(4) . . . . ?
O1 C1 C3 C2 174.6(5) . . . . ?
O3 C1 C3 C2 -1.0(6) . . . . ?
C2 C3 C4 C5 5.3(7) . . . . ?
C1 C3 C4 C5 179.7(5) . . . . ?
C3 C4 C5 C4 -5.9(9) . . . 23 ?
C3 C4 C5 C6 -172.7(5) . . . . ?
C4 C5 C6 C7 83(27) . . . . ?
C4 C5 C6 C7 -83(26) 23 . . . ?
C5 C6 C7 C8 180(100) . . . . ?
C6 C7 C8 C9 92(10) . . . . ?
C6 C7 C8 C9 -92(11) . . . 23 ?
C9 C8 C9 C9 6.5(16) 23 . . 17 ?
C7 C8 C9 C9 -178.3(8) . . . 17 ?
C9 C8 C9 C10 -177.0(7) 23 . . . ?
C7 C8 C9 C10 -1.8(13) . . . . ?
C9 C9 C10 C11 0.0(17) 17 . . . ?
C8 C9 C10 C11 -176.5(10) . . . . ?
C9 C10 C11 C11 -1(2) . . . 17 ?
O3 C1 O1 Cu1 2.9(7) . . . 25_455 ?
C3 C1 O1 Cu1 -172.2(3) . . . 25_455 ?
O1 C1 O3 Cu1 -4.5(7) . . . . ?
C3 C1 O3 Cu1 170.8(3) . . . . ?
O1 Cu1 O3 C1 8.3(8) 25_455 . . . ?
O1 Cu1 O3 C1 86.1(4) 10_455 . . . ?
O3 Cu1 O3 C1 -81.0(4) 22 . . . ?
O1W Cu1 O3 C1 -179.5(4) . . . . ?
Cu1 Cu1 O3 C1 3.0(4) 25_455 . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.769
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.109


_database_code_depnum_ccdc_archive 'CCDC 926773'