# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_im48
_database_code_depnum_ccdc_archive 'CCDC 977911'
_audit_update_record             
;
2013-12-18 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 Cu0.50 O5'
_chemical_formula_weight         268.99

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   P21/c

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                   8.7505(2)
_cell_length_b                   5.0769(2)
_cell_length_c                   26.2226(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.304(3)
_cell_angle_gamma                90.00
_cell_volume                     1157.91(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    7251
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             558
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      140(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 Saphire 3 Xcalibur'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.1852
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8361
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         26.99
_reflns_number_total             2533
_reflns_number_gt                2281
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.35.11'
_computing_cell_refinement       
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.35.11'
_computing_data_reduction        
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.35.11'

_computing_structure_solution    'SIR-97_(Altomare & al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.4.5(CCDC, 2011)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_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)+(0.0421P)²+0.5415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2533
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0765
_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
Cu1 Cu 0.0000 0.0000 0.5000 0.01554(9) Uani 1 2 d S . .
O1 O 0.01854(12) 0.1929(2) 0.56444(4) 0.0177(2) Uani 1 1 d . . .
O2 O 0.16698(13) -0.2397(2) 0.52392(4) 0.0185(2) Uani 1 1 d . . .
O3 O 0.18394(14) 0.2941(3) 0.46946(5) 0.0213(3) Uani 1 1 d . . .
H3A H 0.174(3) 0.418(6) 0.4853(10) 0.050 Uiso 1 1 d . . .
O4 O 0.37035(14) 0.1573(2) 0.68210(4) 0.021 Uani 1 1 d . . .
O5 O 0.50070(13) 0.2446(3) 0.61158(5) 0.025 Uani 1 1 d . . .
C1 C 0.26623(18) -0.1874(3) 0.56189(6) 0.016 Uani 1 1 d . . .
H1 H 0.3505 -0.3055 0.5677 0.019 Uiso 1 1 calc R . .
C2 C 0.26463(19) 0.0221(3) 0.59547(6) 0.0156(3) Uani 1 1 d . . .
C3 C 0.13776(18) 0.1920(3) 0.59682(6) 0.0150(3) Uani 1 1 d . . .
C4 C 0.14205(18) 0.3738(3) 0.64078(6) 0.0162(3) Uani 1 1 d . . .
C5 C 0.03026(19) 0.5674(3) 0.64349(7) 0.0180(3) Uani 1 1 d . . .
H5 H -0.0480 0.5897 0.6157 0.022 Uiso 1 1 calc R . .
C6 C 0.0325(2) 0.7270(3) 0.68621(7) 0.0222(4) Uani 1 1 d . . .
H6 H -0.0444 0.8579 0.6880 0.027 Uiso 1 1 calc R . .
C7 C 0.1481(2) 0.6950(4) 0.72674(7) 0.0254(4) Uani 1 1 d . . .
H7 H 0.1489 0.8039 0.7562 0.030 Uiso 1 1 calc R . .
C8 C 0.2614(2) 0.5080(4) 0.72466(7) 0.0249(4) Uani 1 1 d . . .
H8 H 0.3405 0.4893 0.7523 0.030 Uiso 1 1 calc R . .
C9 C 0.25847(19) 0.3464(3) 0.68156(6) 0.0185(3) Uani 1 1 d . . .
C10 C 0.40410(19) 0.0632(3) 0.63317(6) 0.0179(3) Uani 1 1 d . . .
H10 H 0.4599 -0.1084 0.6383 0.021 Uiso 1 1 calc R . .
C11 C 0.6477(2) 0.2716(6) 0.64092(9) 0.0463(6) Uani 1 1 d . . .
H11A H 0.7096 0.4002 0.6243 0.069 Uiso 1 1 calc R . .
H11B H 0.7003 0.1009 0.6429 0.069 Uiso 1 1 calc R . .
H11C H 0.6338 0.3323 0.6756 0.069 Uiso 1 1 calc R . .
C12 C 0.3437(2) 0.2457(4) 0.46973(8) 0.0289(4) Uani 1 1 d . . .
H12A H 0.3926 0.3979 0.4552 0.043 Uiso 1 1 calc R . .
H12B H 0.3591 0.0890 0.4491 0.043 Uiso 1 1 calc R . .
H12C H 0.3897 0.2166 0.5051 0.043 Uiso 1 1 calc 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
Cu1 O1 1.9444(11) . ?
Cu1 O1 1.9445(11) 3_556 ?
Cu1 O2 1.9515(11) . ?
Cu1 O2 1.9515(11) 3_556 ?
Cu1 O3 2.3970(13) . ?
Cu1 O3 2.3970(13) 3_556 ?
O1 C3 1.2706(19) . ?
O2 C1 1.2752(19) . ?
O3 C12 1.419(2) . ?
O3 H3A 0.76(3) . ?
O4 C9 1.370(2) . ?
O4 C10 1.430(2) . ?
O5 C10 1.410(2) . ?
O5 C11 1.431(2) . ?
C1 C2 1.382(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.409(2) . ?
C2 C10 1.498(2) . ?
C3 C4 1.474(2) . ?
C4 C5 1.394(2) . ?
C4 C9 1.400(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(2) . ?
C8 H8 0.9500 . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 Cu1 O1 180.0 . 3_556 ?
O1 Cu1 O2 92.67(5) . . ?
O1 Cu1 O2 87.33(5) 3_556 . ?
O1 Cu1 O2 87.33(5) . 3_556 ?
O1 Cu1 O2 92.67(5) 3_556 3_556 ?
O2 Cu1 O2 180.00(5) . 3_556 ?
O1 Cu1 O3 88.94(5) . . ?
O1 Cu1 O3 91.06(5) 3_556 . ?
O2 Cu1 O3 89.39(5) . . ?
O2 Cu1 O3 90.61(5) 3_556 . ?
O1 Cu1 O3 91.05(5) . 3_556 ?
O1 Cu1 O3 88.95(5) 3_556 3_556 ?
O2 Cu1 O3 90.61(5) . 3_556 ?
O2 Cu1 O3 89.39(5) 3_556 3_556 ?
O3 Cu1 O3 180.0 . 3_556 ?
C3 O1 Cu1 124.25(10) . . ?
C1 O2 Cu1 122.88(11) . . ?
C12 O3 Cu1 126.00(11) . . ?
C12 O3 H3A 108(2) . . ?
Cu1 O3 H3A 102(2) . . ?
C9 O4 C10 116.28(12) . . ?
C10 O5 C11 112.94(14) . . ?
O2 C1 C2 127.15(15) . . ?
O2 C1 H1 116.4 . . ?
C2 C1 H1 116.4 . . ?
C1 C2 C3 123.38(15) . . ?
C1 C2 C10 117.57(15) . . ?
C3 C2 C10 119.02(14) . . ?
O1 C3 C2 125.22(15) . . ?
O1 C3 C4 117.96(14) . . ?
C2 C3 C4 116.76(14) . . ?
C5 C4 C9 119.11(15) . . ?
C5 C4 C3 121.57(15) . . ?
C9 C4 C3 119.28(15) . . ?
C6 C5 C4 120.52(16) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.61(17) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 121.00(17) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 119.24(17) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
O4 C9 C8 117.04(15) . . ?
O4 C9 C4 122.43(15) . . ?
C8 C9 C4 120.50(16) . . ?
O5 C10 O4 109.50(14) . . ?
O5 C10 C2 107.86(13) . . ?
O4 C10 C2 113.89(13) . . ?
O5 C10 H10 108.5 . . ?
O4 C10 H10 108.5 . . ?
C2 C10 H10 108.5 . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
O2 Cu1 O1 C3 20.35(13) . . . . ?
O2 Cu1 O1 C3 -159.65(13) 3_556 . . . ?
O3 Cu1 O1 C3 -68.99(13) . . . . ?
O3 Cu1 O1 C3 111.01(13) 3_556 . . . ?
O1 Cu1 O2 C1 -18.95(12) . . . . ?
O1 Cu1 O2 C1 161.05(12) 3_556 . . . ?
O3 Cu1 O2 C1 69.96(12) . . . . ?
O3 Cu1 O2 C1 -110.03(12) 3_556 . . . ?
O1 Cu1 O3 C12 97.51(14) . . . . ?
O1 Cu1 O3 C12 -82.49(14) 3_556 . . . ?
O2 Cu1 O3 C12 4.82(14) . . . . ?
O2 Cu1 O3 C12 -175.18(14) 3_556 . . . ?
Cu1 O2 C1 C2 8.0(2) . . . . ?
O2 C1 C2 C3 9.6(3) . . . . ?
O2 C1 C2 C10 -172.26(15) . . . . ?
Cu1 O1 C3 C2 -10.6(2) . . . . ?
Cu1 O1 C3 C4 172.43(10) . . . . ?
C1 C2 C3 O1 -8.3(3) . . . . ?
C10 C2 C3 O1 173.65(15) . . . . ?
C1 C2 C3 C4 168.78(15) . . . . ?
C10 C2 C3 C4 -9.3(2) . . . . ?
O1 C3 C4 C5 -9.0(2) . . . . ?
C2 C3 C4 C5 173.69(15) . . . . ?
O1 C3 C4 C9 168.98(14) . . . . ?
C2 C3 C4 C9 -8.3(2) . . . . ?
C9 C4 C5 C6 -1.2(2) . . . . ?
C3 C4 C5 C6 176.84(15) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C10 O4 C9 C8 -157.03(15) . . . . ?
C10 O4 C9 C4 25.2(2) . . . . ?
C7 C8 C9 O4 -177.75(16) . . . . ?
C7 C8 C9 C4 0.1(3) . . . . ?
C5 C4 C9 O4 178.64(15) . . . . ?
C3 C4 C9 O4 0.6(2) . . . . ?
C5 C4 C9 C8 0.9(2) . . . . ?
C3 C4 C9 C8 -177.14(15) . . . . ?
C11 O5 C10 O4 63.9(2) . . . . ?
C11 O5 C10 C2 -171.71(17) . . . . ?
C9 O4 C10 O5 79.74(17) . . . . ?
C9 O4 C10 C2 -41.1(2) . . . . ?
C1 C2 C10 O5 93.86(17) . . . . ?
C3 C2 C10 O5 -87.94(18) . . . . ?
C1 C2 C10 O4 -144.39(15) . . . . ?
C3 C2 C10 O4 33.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.057
