# Electronic Supplementary Material (ESI) for RSC Advances
# 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
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#  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_b634c2m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            Cu2C27H31O18
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H31 Cu2 O18'
_chemical_formula_weight         770.60

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           Monoclinic
_symmetry_space_group_name_H-M   C2/m

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

_cell_length_a                   16.4482(19)
_cell_length_b                   14.1872(17)
_cell_length_c                   7.1744(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.241(2)
_cell_angle_gamma                90.00
_cell_volume                     1526.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    865
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.47

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             790
_exptl_absorpt_coefficient_mu    1.477
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7566
_exptl_absorpt_correction_T_max  0.8910
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5515
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1829
_reflns_number_gt                1690
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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^)+(0.0694P)^2^+5.5751P] 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_number_reflns         1829
_refine_ls_number_parameters     160
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1271
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.194
_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
C1X C 0.3480(17) -0.0306(18) 0.435(3) 0.080(8) Uani 0.25 1 d PDU A -2
H1X1 H 0.3818 -0.0068 0.5740 0.121 Uiso 0.25 1 calc PR A -2
H1X2 H 0.3775 -0.0867 0.4128 0.121 Uiso 0.25 1 calc PR A -2
H1X3 H 0.2874 -0.0469 0.4179 0.121 Uiso 0.25 1 calc PR A -2
O1X O 0.2954(11) 0.009(2) 0.089(2) 0.055(4) Uani 0.25 1 d PDU A -2
H1X H 0.2415 0.0239 0.0499 0.082 Uiso 0.25 1 calc PR A -2
C2X C 0.344(2) 0.0406(18) 0.290(3) 0.085(9) Uani 0.25 1 d PDU A -2
H2X1 H 0.3151 0.0977 0.3147 0.101 Uiso 0.25 1 calc PR A -2
H2X2 H 0.4051 0.0576 0.3091 0.101 Uiso 0.25 1 calc PR A -2
C1S C 0.2852(14) 0.0000 0.023(4) 0.055(4) Uani 0.50 2 d SPDU B 1
H1S1 H 0.2595 0.0113 -0.1252 0.082 Uiso 0.25 1 calc PR B 1
H1S2 H 0.2661 0.0499 0.0901 0.082 Uiso 0.25 1 calc PR B 1
H1S3 H 0.2648 -0.0612 0.0503 0.082 Uiso 0.25 1 calc PR B 1
C2S C 0.4368(9) 0.0000 0.301(3) 0.062(5) Uani 0.50 2 d SPD . 1
C4S C 0.4721(9) 0.0000 0.661(2) 0.058(4) Uani 0.50 2 d SPD . 1
C3S C 0.4089(10) 0.0000 0.460(2) 0.066(5) Uani 0.50 2 d SPD C 1
H3S H 0.3471 0.0000 0.4313 0.079 Uiso 0.50 2 calc SPR C 1
C5S C 0.4351(12) 0.0000 0.808(3) 0.062(5) Uani 0.50 2 d SP . 1
O1S O 0.3768(8) 0.0000 0.096(2) 0.071(3) Uani 0.50 2 d SPD B 1
O3S O 0.3512(9) 0.0000 0.751(2) 0.080(4) Uani 0.50 2 d SP D 1
H3S1 H 0.3393 0.0000 0.8541 0.120 Uiso 0.50 2 calc SPR D 1
O2S O 0.4827(19) 0.0000 1.008(6) 0.110(7) Uani 0.50 2 d SPU . 1
Cu1 Cu 0.53876(3) 0.5000 0.69769(7) 0.00678(18) Uani 1 2 d S . .
O1 O 0.55116(14) 0.59469(16) 0.3205(3) 0.0160(5) Uani 1 1 d . . .
O2 O 0.61571(15) 0.59666(17) 0.6615(3) 0.0180(5) Uani 1 1 d . . .
O3 O 0.6047(2) 0.5000 1.0268(5) 0.0162(7) Uani 1 2 d S . .
H3O H 0.597(3) 0.537(3) 1.083(6) 0.019 Uiso 1 1 d . . .
O4 O 0.60938(14) 0.71352(16) 0.1265(3) 0.0160(5) Uani 1 1 d . . .
C1 C 0.61036(18) 0.6217(2) 0.4886(4) 0.0102(5) Uani 1 1 d . . .
C2 C 0.68112(19) 0.6884(2) 0.4868(4) 0.0111(6) Uani 1 1 d . . .
C3 C 0.67867(19) 0.7328(2) 0.3087(4) 0.0117(6) Uani 1 1 d . . .
C4 C 0.75253(19) 0.7063(2) 0.6738(4) 0.0118(6) Uani 1 1 d . . .
H4 H 0.7541 0.6758 0.7930 0.014 Uiso 1 1 calc R . .
C5 C 0.5997(2) 0.7711(2) -0.0449(5) 0.0174(6) Uani 1 1 d . . .
H5A H 0.5478 0.7499 -0.1655 0.026 Uiso 1 1 calc R . .
H5B H 0.6534 0.7660 -0.0714 0.026 Uiso 1 1 calc R . .
H5C H 0.5912 0.8369 -0.0153 0.026 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
C1X 0.076(11) 0.077(12) 0.090(11) 0.023(8) 0.036(9) -0.033(8)
O1X 0.033(5) 0.069(7) 0.050(10) 0.037(9) 0.004(6) 0.005(8)
C2X 0.085(12) 0.091(13) 0.085(12) 0.011(9) 0.043(9) 0.003(9)
C1S 0.033(5) 0.069(7) 0.050(10) 0.037(9) 0.004(6) 0.005(8)
C2S 0.043(8) 0.044(9) 0.079(12) 0.000 0.006(8) 0.000
C4S 0.048(9) 0.056(10) 0.072(11) 0.000 0.026(8) 0.000
C3S 0.033(7) 0.071(12) 0.085(13) 0.000 0.017(8) 0.000
C5S 0.052(9) 0.044(9) 0.096(14) 0.000 0.035(10) 0.000
O1S 0.053(7) 0.069(8) 0.083(9) 0.000 0.019(6) 0.000
O3S 0.077(9) 0.064(8) 0.093(10) 0.000 0.030(8) 0.000
O2S 0.119(13) 0.098(8) 0.104(9) 0.000 0.037(8) 0.000
Cu1 0.0058(3) 0.0067(3) 0.0092(3) 0.000 0.00448(18) 0.000
O1 0.0142(10) 0.0185(11) 0.0137(10) 0.0009(8) 0.0042(8) -0.0095(9)
O2 0.0182(11) 0.0226(12) 0.0141(10) -0.0018(9) 0.0075(9) -0.0127(9)
O3 0.0197(16) 0.0194(17) 0.0111(15) 0.000 0.0080(12) 0.000
O4 0.0144(10) 0.0209(11) 0.0105(10) 0.0007(8) 0.0028(8) -0.0086(9)
C1 0.0096(12) 0.0080(12) 0.0159(13) -0.0006(10) 0.0082(11) 0.0003(10)
C2 0.0103(13) 0.0113(13) 0.0141(13) -0.0015(10) 0.0073(11) -0.0032(10)
C3 0.0096(12) 0.0132(13) 0.0122(13) -0.0021(11) 0.0042(10) -0.0028(11)
C4 0.0126(13) 0.0123(14) 0.0124(13) 0.0003(10) 0.0071(11) -0.0011(11)
C5 0.0168(14) 0.0199(16) 0.0136(13) 0.0025(12) 0.0044(11) -0.0054(12)

_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
C1X C2X 1.430(18) . ?
O1X C2X 1.409(18) . ?
C1S O1S 1.377(19) . ?
C2S O1S 1.39(2) . ?
C2S C3S 1.394(10) . ?
C2S C4S 1.408(9) 5_656 ?
C4S C3S 1.389(10) . ?
C4S C2S 1.408(9) 5_656 ?
C4S C5S 1.42(2) . ?
C5S O3S 1.27(2) . ?
C5S O2S 1.32(4) . ?
C5S O2S 1.45(4) 5_657 ?
O2S O2S 0.62(5) 5_657 ?
O2S C5S 1.45(4) 5_657 ?
Cu1 O2 1.954(2) . ?
Cu1 O2 1.954(2) 6_565 ?
Cu1 O1 1.962(2) 5_666 ?
Cu1 O1 1.962(2) 2_656 ?
Cu1 O3 2.156(3) . ?
Cu1 Cu1 2.5889(9) 5_666 ?
O1 C1 1.259(4) . ?
O1 Cu1 1.962(2) 5_666 ?
O2 C1 1.259(4) . ?
O4 C3 1.363(3) . ?
O4 C5 1.430(4) . ?
C1 C2 1.504(4) . ?
C2 C4 1.396(4) . ?
C2 C3 1.410(4) . ?
C3 C4 1.388(4) 7_666 ?
C4 C3 1.388(4) 7_666 ?

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
O1X C2X C1X 111.0(18) . . ?
O1S C2S C3S 122.3(13) . . ?
O1S C2S C4S 116.1(15) . 5_656 ?
C3S C2S C4S 121.6(14) . 5_656 ?
C3S C4S C2S 118.9(14) . 5_656 ?
C3S C4S C5S 113.8(15) . . ?
C2S C4S C5S 127.2(16) 5_656 . ?
C4S C3S C2S 119.5(14) . . ?
O3S C5S O2S 115(2) . . ?
O3S C5S C4S 120.3(18) . . ?
O2S C5S C4S 124.2(19) . . ?
O3S C5S O2S 141(2) . 5_657 ?
O2S C5S O2S 25(2) . 5_657 ?
C4S C5S O2S 98.8(17) . 5_657 ?
C1S O1S C2S 126.5(17) . . ?
O2S O2S C5S 89(7) 5_657 . ?
O2S O2S C5S 65(6) 5_657 5_657 ?
C5S O2S C5S 155(2) . 5_657 ?
O2 Cu1 O2 89.13(15) . 6_565 ?
O2 Cu1 O1 169.43(9) . 5_666 ?
O2 Cu1 O1 91.28(11) 6_565 5_666 ?
O2 Cu1 O1 91.28(11) . 2_656 ?
O2 Cu1 O1 169.43(9) 6_565 2_656 ?
O1 Cu1 O1 86.41(14) 5_666 2_656 ?
O2 Cu1 O3 94.79(9) . . ?
O2 Cu1 O3 94.79(9) 6_565 . ?
O1 Cu1 O3 95.71(9) 5_666 . ?
O1 Cu1 O3 95.71(9) 2_656 . ?
O2 Cu1 Cu1 84.78(7) . 5_666 ?
O2 Cu1 Cu1 84.78(7) 6_565 5_666 ?
O1 Cu1 Cu1 84.74(7) 5_666 5_666 ?
O1 Cu1 Cu1 84.74(7) 2_656 5_666 ?
O3 Cu1 Cu1 179.39(9) . 5_666 ?
C1 O1 Cu1 122.55(19) . 5_666 ?
C1 O2 Cu1 122.83(19) . . ?
C3 O4 C5 117.6(2) . . ?
O2 C1 O1 124.9(3) . . ?
O2 C1 C2 116.4(2) . . ?
O1 C1 C2 118.7(2) . . ?
C4 C2 C3 119.3(3) . . ?
C4 C2 C1 117.0(2) . . ?
C3 C2 C1 123.6(3) . . ?
O4 C3 C4 122.8(3) . 7_666 ?
O4 C3 C2 118.7(3) . . ?
C4 C3 C2 118.5(3) 7_666 . ?
C3 C4 C2 122.2(3) 7_666 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1X H1X O3 0.84 2.21 2.985(18) 152.5 3_444
O3S H3S1 O1S 0.84 1.59 2.34(2) 147.0 1_556
O3 H3O O1 0.70(4) 2.29(4) 2.923(4) 153(4) 1_556
O3 H3O O4 0.70(4) 2.53(4) 3.106(2) 142(4) 1_556

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.133
_database_code_depnum_ccdc_archive 'CCDC 898032'