# 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_20120615
_database_code_depnum_ccdc_archive 'CCDC 981571'
_audit_update_record             
;
2014-01-15 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 Cu0.28 O4 Zn0.67'
_chemical_formula_sum            'C10 H14 Cu0.28 O4 Zn0.67'
_chemical_formula_weight         259.82

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   10.329(4)
_cell_length_b                   4.6947(18)
_cell_length_c                   11.369(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.881(6)
_cell_angle_gamma                90.00
_cell_volume                     551.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1261
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      25.68

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.97
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.014
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    2.044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6005
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3905
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         28.22
_reflns_number_total             1356
_reflns_number_gt                1017
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0401P)²+0.2077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1356
_refine_ls_number_parameters     74
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.046
_refine_ls_shift/su_mean         0.003

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
Zn1 Zn 0.0000 0.0000 0.0000 0.03672(18) Uani 0.67(7) 2 d SP . .
Cu1' Cu 0.0000 0.0000 0.0000 0.03672(18) Uani 0.28(7) 2 d SP . .
O1 O 0.16142(16) 0.2020(4) 0.00589(16) 0.0430(5) Uani 1 1 d . . .
O2 O -0.06526(16) 0.1953(4) 0.13398(15) 0.0429(5) Uani 1 1 d . . .
C5 C 0.1085(3) 0.5193(6) 0.1582(2) 0.0426(6) Uani 1 1 d . . .
H5 H 0.1371 0.6783 0.2003 0.051 Uiso 1 1 calc R . .
C4 C -0.0870(3) 0.5392(6) 0.2823(3) 0.0537(8) Uani 1 1 d . . .
H4A H -0.1661 0.4354 0.2913 0.081 Uiso 1 1 calc R . .
H4B H -0.1067 0.7336 0.2624 0.081 Uiso 1 1 calc R . .
H4C H -0.0366 0.5334 0.3547 0.081 Uiso 1 1 calc R . .
C1 C 0.1886(2) 0.4135(6) 0.0730(2) 0.0368(6) Uani 1 1 d . . .
C2 C -0.0112(3) 0.4065(6) 0.1857(2) 0.0384(6) Uani 1 1 d . . .
C3 C 0.3164(3) 0.5538(6) 0.0527(3) 0.0500(7) Uani 1 1 d . . .
H3A H 0.3753 0.4167 0.0219 0.075 Uiso 1 1 calc R . .
H3B H 0.3513 0.6279 0.1257 0.075 Uiso 1 1 calc R . .
H3C H 0.3043 0.7067 -0.0027 0.075 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
Zn1 0.0367(3) 0.0315(3) 0.0425(3) -0.0061(2) 0.00878(17) -0.0039(2)
Cu1' 0.0367(3) 0.0315(3) 0.0425(3) -0.0061(2) 0.00878(17) -0.0039(2)
O1 0.0412(10) 0.0367(10) 0.0516(11) -0.0066(8) 0.0107(8) -0.0028(8)
O2 0.0438(10) 0.0363(10) 0.0491(11) -0.0071(8) 0.0117(8) -0.0049(8)
C5 0.0434(13) 0.0421(15) 0.0422(14) -0.0081(12) 0.0025(10) -0.0060(12)
C4 0.0582(18) 0.053(2) 0.0507(17) -0.0160(13) 0.0172(13) -0.0034(14)
C1 0.0383(13) 0.0315(12) 0.0405(13) 0.0021(10) -0.0021(10) -0.0008(10)
C2 0.0447(14) 0.0336(12) 0.0371(13) -0.0003(10) 0.0041(11) 0.0025(11)
C3 0.0422(14) 0.0507(18) 0.0574(17) -0.0032(13) 0.0060(12) -0.0085(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
Zn1 O1 1.9174(18) 3 ?
Zn1 O1 1.9174(18) . ?
Zn1 O2 1.9191(17) 3 ?
Zn1 O2 1.9191(17) . ?
O1 C1 1.278(3) . ?
O2 C2 1.272(3) . ?
C5 C1 1.387(4) . ?
C5 C2 1.390(4) . ?
C4 C2 1.505(4) . ?
C1 C3 1.499(4) . ?

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 Zn1 O1 180.00(5) 3 . ?
O1 Zn1 O2 93.65(7) 3 3 ?
O1 Zn1 O2 86.35(7) . 3 ?
O1 Zn1 O2 86.35(7) 3 . ?
O1 Zn1 O2 93.65(7) . . ?
O2 Zn1 O2 180.00(11) 3 . ?
C1 O1 Zn1 125.40(17) . . ?
C2 O2 Zn1 125.37(17) . . ?
C1 C5 C2 125.2(2) . . ?
O1 C1 C5 124.8(2) . . ?
O1 C1 C3 115.3(2) . . ?
C5 C1 C3 119.9(2) . . ?
O2 C2 C5 125.0(2) . . ?
O2 C2 C4 115.4(2) . . ?
C5 C2 C4 119.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.22
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.062
