# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 1867351'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H22 Cu2 O13'
_chemical_formula_weight         477.35

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.9885(2)
_cell_length_b                   11.9939(2)
_cell_length_c                   14.1518(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1695.40(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8647
_cell_measurement_theta_min      2.8540
_cell_measurement_theta_max      31.6240

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.211
_exptl_absorpt_coefficient_mu    2.574
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.321
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1268
_diffrn_reflns_number            13228
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.654
_diffrn_reflns_theta_max         31.882
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2801
_reflns_number_gt                2706
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²+0.8872P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.005(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2801
_refine_ls_number_parameters     135
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0213
_refine_ls_wR_factor_ref         0.0494
_refine_ls_wR_factor_gt          0.0489
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.070
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2641(2) 0.44717(16) 0.71787(15) 0.0162(4) Uani 1 1 d . . . . .
C2 C 0.2601(2) 0.46064(17) 0.82497(15) 0.0186(4) Uani 1 1 d . . . . .
H2 H 0.169(3) 0.4898(9) 0.8427(5) 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2818(2) 0.35097(18) 0.87736(14) 0.0183(4) Uani 1 1 d . . . . .
C4 C 0.3647(3) 0.54648(19) 0.85801(17) 0.0269(5) Uani 1 1 d . . . . .
H4A H 0.3642(3) 0.5491(2) 0.9264(15) 0.032 Uiso 1 1 calc R U . . .
H4B H 0.453(2) 0.5217(6) 0.8382(5) 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3412(4) 0.6631(2) 0.8202(3) 0.0459(8) Uani 1 1 d . . . . .
H5A H 0.345(3) 0.6620(5) 0.7538(16) 0.069 Uiso 1 1 calc R U . . .
H5B H 0.408(2) 0.7114(12) 0.8437(16) 0.069 Uiso 1 1 calc R U . . .
H5C H 0.256(2) 0.6884(11) 0.8397(16) 0.069 Uiso 1 1 calc R U . . .
Cu1 Cu 0.5000 0.30127(3) 0.7500 0.01738(8) Uani 1 2 d S T P . .
Cu2 Cu 0.17474(4) 0.5000 0.5000 0.01816(8) Uani 1 2 d S T P . .
O1 O 0.17624(17) 0.49325(16) 0.66904(10) 0.0245(3) Uani 1 1 d . . . . .
O2 O 0.35978(16) 0.39171(14) 0.68127(11) 0.0204(3) Uani 1 1 d . . . . .
O3 O 0.19825(18) 0.32308(16) 0.93742(14) 0.0343(5) Uani 1 1 d . . . . .
O4 O 0.38650(16) 0.29278(14) 0.86168(10) 0.0212(3) Uani 1 1 d . . . . .
O1W O 0.5000 0.13456(18) 0.7500 0.0324(6) Uani 1 2 d DS T P . .
H1W H 0.570(3) 0.101(3) 0.729(2) 0.049 Uiso 1 1 d D U . . .
O2W O 0.32076(17) 0.61050(14) 0.50634(13) 0.0251(3) Uani 1 1 d D . . . .
H2W1 H 0.349(3) 0.619(3) 0.4506(16) 0.038 Uiso 1 1 d D U . . .
H2W2 H 0.308(3) 0.6798(18) 0.520(2) 0.038 Uiso 1 1 d D U . . .
O3W O 0.03607(18) 0.38527(15) 0.48145(13) 0.0325(4) Uani 1 1 d D . . . .
H3W1 H 0.056(4) 0.330(2) 0.444(2) 0.049 Uiso 1 1 d D U . . .
H3W2 H -0.035(3) 0.372(3) 0.514(2) 0.049 Uiso 1 1 d D U . . .

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 0.0184(9) 0.0146(9) 0.0156(8) 0.0019(7) 0.0016(7) 0.0013(7)
C2 0.0248(11) 0.0162(9) 0.0148(9) 0.0024(7) 0.0043(8) 0.0065(8)
C3 0.0218(10) 0.0175(9) 0.0157(9) 0.0020(7) 0.0041(7) 0.0030(8)
C4 0.0373(14) 0.0193(10) 0.0241(10) -0.0018(9) -0.0036(10) 0.0034(10)
C5 0.0551(19) 0.0202(11) 0.062(2) 0.0028(12) -0.0115(18) -0.0003(13)
Cu1 0.01840(16) 0.01741(16) 0.01633(15) 0.000 0.00538(16) 0.000
Cu2 0.01811(17) 0.01587(15) 0.02050(16) -0.00274(14) 0.000 0.000
O1 0.0258(7) 0.0297(8) 0.0180(6) 0.0021(6) 0.0000(6) 0.0128(8)
O2 0.0202(7) 0.0262(8) 0.0149(6) 0.0002(6) 0.0005(6) 0.0086(6)
O3 0.0329(9) 0.0311(9) 0.0388(10) 0.0167(8) 0.0217(8) 0.0135(8)
O4 0.0234(7) 0.0197(7) 0.0206(7) 0.0061(6) 0.0075(6) 0.0070(6)
O1W 0.0343(13) 0.0145(9) 0.0483(15) 0.000 0.0261(14) 0.000
O2W 0.0300(8) 0.0225(7) 0.0229(7) -0.0044(7) 0.0036(9) -0.0051(6)
O3W 0.0298(9) 0.0294(9) 0.0382(11) -0.0154(8) 0.0160(8) -0.0128(7)

_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 1.246(3) . ?
C1 O2 1.275(3) . ?
C1 C2 1.525(3) . ?
C2 C3 1.525(3) . ?
C2 C4 1.540(3) . ?
C2 H2 1.01(3) . ?
C3 O3 1.237(3) . ?
C3 O4 1.277(3) . ?
C4 C5 1.516(3) . ?
C4 H4A 0.97(2) . ?
C4 H4B 0.97(2) . ?
C5 H5A 0.94(2) . ?
C5 H5B 0.94(2) . ?
C5 H5C 0.94(2) . ?
Cu1 O4 1.9477(14) . ?
Cu1 O4 1.9477(14) 3_656 ?
Cu1 O1W 1.999(2) . ?
Cu1 O2 2.0209(15) . ?
Cu1 O2 2.0210(15) 3_656 ?
Cu2 O3W 1.9700(17) . ?
Cu2 O3W 1.9700(17) 4_566 ?
Cu2 O2W 1.9727(17) 4_566 ?
Cu2 O2W 1.9727(17) . ?
Cu2 O1 2.3936(14) 4_566 ?
Cu2 O1 2.3936(14) . ?
O1W H1W 0.86(2) . ?
O2W H2W1 0.85(2) . ?
O2W H2W2 0.86(2) . ?
O3W H3W1 0.88(2) . ?
O3W H3W2 0.87(2) . ?

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 O2 122.3(2) . . ?
O1 C1 C2 119.07(18) . . ?
O2 C1 C2 118.60(19) . . ?
C1 C2 C3 112.84(17) . . ?
C1 C2 C4 110.80(18) . . ?
C3 C2 C4 109.44(18) . . ?
C1 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
C4 C2 H2 107.9 . . ?
O3 C3 O4 121.6(2) . . ?
O3 C3 C2 118.13(19) . . ?
O4 C3 C2 120.20(18) . . ?
C5 C4 C2 113.9(2) . . ?
C5 C4 H4A 108.8 . . ?
C2 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C2 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 Cu1 O4 174.01(10) . 3_656 ?
O4 Cu1 O1W 87.00(5) . . ?
O4 Cu1 O1W 87.00(5) 3_656 . ?
O4 Cu1 O2 90.87(6) . . ?
O4 Cu1 O2 92.35(7) 3_656 . ?
O1W Cu1 O2 122.46(5) . . ?
O4 Cu1 O2 92.35(7) . 3_656 ?
O4 Cu1 O2 90.87(7) 3_656 3_656 ?
O1W Cu1 O2 122.47(5) . 3_656 ?
O2 Cu1 O2 115.07(10) . 3_656 ?
O3W Cu2 O3W 90.65(11) . 4_566 ?
O3W Cu2 O2W 92.55(7) . 4_566 ?
O3W Cu2 O2W 174.35(8) 4_566 4_566 ?
O3W Cu2 O2W 174.35(8) . . ?
O3W Cu2 O2W 92.55(8) 4_566 . ?
O2W Cu2 O2W 84.65(11) 4_566 . ?
O3W Cu2 O1 83.96(7) . 4_566 ?
O3W Cu2 O1 96.54(7) 4_566 4_566 ?
O2W Cu2 O1 88.43(7) 4_566 4_566 ?
O2W Cu2 O1 91.04(7) . 4_566 ?
O3W Cu2 O1 96.54(7) . . ?
O3W Cu2 O1 83.97(7) 4_566 . ?
O2W Cu2 O1 91.04(7) 4_566 . ?
O2W Cu2 O1 88.43(7) . . ?
O1 Cu2 O1 179.28(8) 4_566 . ?
C1 O1 Cu2 125.01(14) . . ?
C1 O2 Cu1 127.18(14) . . ?
C3 O4 Cu1 126.11(14) . . ?
Cu1 O1W H1W 118(2) . . ?
Cu2 O2W H2W1 107(2) . . ?
Cu2 O2W H2W2 123(2) . . ?
H2W1 O2W H2W2 99(3) . . ?
Cu2 O3W H3W1 117(2) . . ?
Cu2 O3W H3W2 129(2) . . ?
H3W1 O3W H3W2 112(3) . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4

_shelx_res_file                  
;
TITL ull2815_a.res in C222(1)
CELL  0.71073   9.9885  11.9939  14.1518   90.000   90.000   90.000
ZERR     4.00   0.0002   0.0002   0.0003    0.000    0.000    0.000
LATT  -7
SYMM  - X, - Y, 1/2 + Z
SYMM  - X,   Y, 1/2 - Z
SYMM    X, - Y, - Z
SFAC  C    H    CU   O
UNIT  40   88   8    52
MERG   2
TWIN
DFIX   0.95 0.02 O1W H1W O2W H2W1 O2W H2W2 O3W H3W1 O3W H3W2
FMAP   2
PLAN   12
ACTA
BOND   $H
LIST   6
L.S.   4
WGHT    0.021300    0.887200
BASF   0.00471
FVAR       3.58914
C1    1    0.264077    0.447168    0.717868    11.00000    0.01837    0.01464 =
         0.01562    0.00193    0.00163    0.00131
C2    1    0.260101    0.460635    0.824966    11.00000    0.02480    0.01618 =
         0.01477    0.00237    0.00427    0.00650
AFIX  14
H2    2    0.168575    0.489842    0.842671    11.00000   -1.20000
AFIX   0
C3    1    0.281768    0.350967    0.877358    11.00000    0.02179    0.01753 =
         0.01568    0.00199    0.00405    0.00299
C4    1    0.364695    0.546483    0.858009    11.00000    0.03733    0.01932 =
         0.02413   -0.00175   -0.00357    0.00338
AFIX  24
H4A   2    0.364224    0.549097    0.926422    11.00000   -1.20000
H4B   2    0.452619    0.521671    0.838212    11.00000   -1.20000
AFIX   0
C5    1    0.341186    0.663126    0.820224    11.00000    0.05507    0.02015 =
         0.06238    0.00276   -0.01146   -0.00026
AFIX 138
H5A   2    0.344987    0.662035    0.753758    11.00000   -1.50000
H5B   2    0.407645    0.711376    0.843744    11.00000   -1.50000
H5C   2    0.256328    0.688403    0.839704    11.00000   -1.50000
AFIX   0
CU1   3    0.500000    0.301268    0.750000    10.50000    0.01840    0.01741 =
         0.01633    0.00000    0.00538    0.00000
CU2   3    0.174740    0.500000    0.500000    10.50000    0.01811    0.01587 =
         0.02050   -0.00274    0.00000    0.00000
O1    4    0.176242    0.493249    0.669039    11.00000    0.02577    0.02965 =
         0.01802    0.00207   -0.00004    0.01276
O2    4    0.359785    0.391713    0.681273    11.00000    0.02015    0.02616 =
         0.01491    0.00024    0.00054    0.00861
O3    4    0.198254    0.323080    0.937425    11.00000    0.03290    0.03112 =
         0.03883    0.01669    0.02167    0.01348
O4    4    0.386497    0.292779    0.861676    11.00000    0.02337    0.01974 =
         0.02059    0.00612    0.00753    0.00697
MOLE    1
O1W   4    0.500000    0.134564    0.750000    10.50000    0.03435    0.01454 =
         0.04826    0.00000    0.02608    0.00000
H1W   2    0.569518    0.100917    0.728615    11.00000   -1.50000
MOLE    2
O2W   4    0.320757    0.610496    0.506339    11.00000    0.02997    0.02250 =
         0.02287   -0.00442    0.00358   -0.00511
H2W1  2    0.349432    0.618734    0.450593    11.00000   -1.50000
H2W2  2    0.307897    0.679818    0.520140    11.00000   -1.50000
MOLE    3
O3W   4    0.036072    0.385273    0.481450    11.00000    0.02981    0.02938 =
         0.03820   -0.01540    0.01603   -0.01279
H3W1  2    0.056438    0.329502    0.444001    11.00000   -1.50000
H3W2  2   -0.035396    0.372198    0.514251    11.00000   -1.50000
HKLF    4

REM  ull2815_a.res in C222(1)
REM R1 =  0.0213 for    2706 Fo > 4sig(Fo)  and  0.0225 for all    2801 data
REM    135 parameters refined using      5 restraints

END

WGHT      0.0213      0.8875

REM Highest difference peak  0.242,  deepest hole -0.440,  1-sigma level  0.053
Q1    1   0.2755  0.4045  0.8562  11.00000  0.05    0.24
Q2    1   0.3338  0.5995  0.8337  11.00000  0.05    0.23
Q3    1   0.0891  0.3612  0.5046  11.00000  0.05    0.22
Q4    1   0.2767  0.4530  0.7699  11.00000  0.05    0.22
Q5    1   0.5129  0.2711  0.7990  11.00000  0.05    0.21
Q6    1   0.4972  0.2016  0.7299  11.00000  0.05    0.20
Q7    1   0.0196  0.3734  0.4552  11.00000  0.05    0.20
Q8    1   0.3217  0.5045  0.8284  11.00000  0.05    0.19
Q9    1   0.1788  0.5291  0.5539  11.00000  0.05    0.19
Q10   1   0.2352  0.4372  0.7529  11.00000  0.05    0.19
Q11   1   0.4552  0.7497  0.7495  11.00000  0.05    0.19
Q12   1   0.0810  0.4277  0.4828  11.00000  0.05    0.18
;
_shelx_res_checksum              58460


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_compound3
_database_code_depnum_ccdc_archive 'CCDC 1867353'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_compound3           
;
PROBLEM: Short Inter D...A Contact  O2W      ..O3W      .       2.29 Ang.
RESPONSE: Disordered water molecules in the voids of the structure
;
_vrf_PLAT430_compound3_2         
;
PROBLEM: Short Inter D...A Contact  O2W      ..O2W      .       2.55 Ang.
RESPONSE: Disordered water molecules in the voids of the structure
;
# Added during the CSD deposition process: Wednesday 12 September 2018 11:46 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H6 Cu O6'
_chemical_formula_weight         225.64

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z+2/3'
'y, -x+y, z+1/6'
'-x+y, -x, z+1/3'
'x-y, x, z+5/6'

_cell_length_a                   11.5965(8)
_cell_length_b                   11.5965(8)
_cell_length_c                   10.5437(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1227.94(18)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7648
_cell_measurement_theta_min      2.801
_cell_measurement_theta_max      28.655

_exptl_crystal_description       Needle
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_F_000             678
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    2.656
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'KappaCCD Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            7648
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.801
_diffrn_reflns_theta_max         28.655
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1916
_reflns_number_gt                1813
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²+1.5899P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1916
_refine_ls_number_parameters     120
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4993(8) 0.8605(7) 0.1851(7) 0.0205(14) Uani 1 1 d . . . . .
C2 C 0.5490(8) 0.9324(7) 0.0582(7) 0.0223(15) Uani 1 1 d . . . . .
H2 H 0.6433 0.9999 0.0667 0.027 Uiso 1 1 calc R U . . .
C3 C 0.4716(7) 1.0009(7) 0.0197(7) 0.0189(14) Uani 1 1 d . . . . .
C4 C 0.5355(11) 0.8294(9) -0.0409(8) 0.035(2) Uani 1 1 d . . . . .
H4A H 0.5971 0.7987 -0.0200 0.042 Uiso 1 1 calc R U . . .
H4B H 0.4461 0.7533 -0.0367 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5627(17) 0.8833(13) -0.1761(12) 0.065(4) Uani 1 1 d . . . . .
H5A H 0.5518 0.8143 -0.2335 0.097 Uiso 1 1 calc R U . . .
H5B H 0.6521 0.9568 -0.1818 0.097 Uiso 1 1 calc R U . . .
H5C H 0.5012 0.9128 -0.1980 0.097 Uiso 1 1 calc R U . . .
Cu1 Cu 0.23434(9) 0.75821(8) 0.08617(14) 0.0216(3) Uani 1 1 d . . . . .
O1 O 0.5876(5) 0.8765(5) 0.2648(5) 0.0231(11) Uani 1 1 d . . . . .
O2 O 0.3766(6) 0.7868(6) 0.2067(5) 0.0260(12) Uani 1 1 d . . . . .
O3 O 0.5392(5) 1.1218(5) -0.0068(6) 0.0225(12) Uani 1 1 d . . . . .
O4 O 0.3471(6) 0.9341(5) 0.0117(6) 0.0281(12) Uani 1 1 d . . . . .
O1W O 0.1227(8) 0.8553(8) 0.1785(9) 0.056(2) Uani 1 1 d . . . . .
O2W O 0.8165(16) 0.895(2) 0.130(2) 0.067(5) Uani 0.5 1 d . . P . .
O3W O 0.083(2) 1.001(3) 0.386(3) 0.107(9) Uani 0.5 1 d . . P . .

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 0.025(3) 0.014(3) 0.021(4) 0.000(3) 0.001(3) 0.009(3)
C2 0.028(4) 0.019(3) 0.023(4) 0.005(3) 0.004(3) 0.014(3)
C3 0.021(3) 0.019(3) 0.013(4) 0.000(2) -0.001(3) 0.008(3)
C4 0.062(6) 0.027(4) 0.026(4) 0.002(3) 0.003(4) 0.031(4)
C5 0.106(12) 0.046(7) 0.033(6) 0.001(5) 0.026(6) 0.032(7)
Cu1 0.0202(5) 0.0169(4) 0.0217(5) 0.0015(3) -0.0014(4) 0.0046(3)
O1 0.025(2) 0.027(3) 0.019(3) 0.007(2) 0.003(2) 0.014(2)
O2 0.020(3) 0.031(3) 0.019(3) 0.008(2) -0.0014(19) 0.006(2)
O3 0.020(2) 0.014(2) 0.033(3) 0.005(2) 0.000(2) 0.009(2)
O4 0.030(3) 0.021(3) 0.029(3) 0.009(2) -0.001(2) 0.010(2)
O1W 0.043(4) 0.039(4) 0.082(6) 0.005(4) 0.034(4) 0.017(4)
O2W 0.032(8) 0.088(14) 0.083(14) 0.022(10) 0.002(7) 0.029(9)
O3W 0.071(15) 0.12(2) 0.14(3) -0.045(18) -0.023(15) 0.049(15)

_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 O2 1.261(10) . ?
C1 O1 1.264(10) . ?
C1 C2 1.528(10) . ?
C2 C3 1.521(11) . ?
C2 C4 1.535(11) . ?
C3 O3 1.249(9) . ?
C3 O4 1.255(9) . ?
C4 C5 1.525(15) . ?
Cu1 O3 1.948(5) 4_455 ?
Cu1 O4 1.954(5) . ?
Cu1 O2 1.974(5) . ?
Cu1 O1 1.977(5) 3_664 ?
Cu1 O1W 2.313(8) . ?
O1 Cu1 1.978(5) 5_565 ?
O3 Cu1 1.948(5) 6_664 ?

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 C1 O1 122.4(7) . . ?
O2 C1 C2 121.2(7) . . ?
O1 C1 C2 116.4(7) . . ?
C3 C2 C1 111.0(6) . . ?
C3 C2 C4 111.6(7) . . ?
C1 C2 C4 107.9(6) . . ?
O3 C3 O4 124.1(7) . . ?
O3 C3 C2 116.3(6) . . ?
O4 C3 C2 119.5(7) . . ?
C5 C4 C2 113.4(7) . . ?
O3 Cu1 O4 179.8(3) 4_455 . ?
O3 Cu1 O2 89.2(2) 4_455 . ?
O4 Cu1 O2 90.9(2) . . ?
O3 Cu1 O1 92.1(2) 4_455 3_664 ?
O4 Cu1 O1 87.7(2) . 3_664 ?
O2 Cu1 O1 161.9(2) . 3_664 ?
O3 Cu1 O1W 95.5(2) 4_455 . ?
O4 Cu1 O1W 84.6(3) . . ?
O2 Cu1 O1W 105.7(3) . . ?
O1 Cu1 O1W 92.1(3) 3_664 . ?
C1 O1 Cu1 116.2(5) . 5_565 ?
C1 O2 Cu1 124.2(5) . . ?
C3 O3 Cu1 127.4(5) . 6_664 ?
C3 O4 Cu1 125.5(5) . . ?

_refine_diff_density_max         0.721
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.124

_shelxl_version_number           2013-4

_shelx_res_file                  
;
TITL import in P 65
CELL  0.71073  11.5965  11.5965  10.5437   90.000   90.000  120.000
ZERR     6.00   0.0008   0.0008   0.0006    0.000    0.000    0.000
LATT  -1
SYMM  - X, - Y, 1/2 + Z
SYMM  - Y,   X - Y, 2/3 + Z
SYMM    Y, - X + Y, 1/6 + Z
SYMM  - X + Y, - X, 1/3 + Z
SYMM    X - Y,   X, 5/6 + Z
SFAC  C    H    CU   O
UNIT  30   36   6    36
MERG   2
OMIT  0 1 0
TWIN
FMAP   2
PLAN   20
ACTA
BOND
L.S.   9
WGHT    0.074600    1.589900
EXTI    0.017881
BASF   0.03805
FVAR       1.60431
C1    1    0.499295    0.860547    0.185105    11.00000    0.02514    0.01371 =
         0.02119   -0.00020    0.00111    0.00867
C2    1    0.548987    0.932415    0.058219    11.00000    0.02771    0.01914 =
         0.02305    0.00513    0.00439    0.01403
AFIX  13
H2    2    0.643300    0.999860    0.066658    11.00000   -1.20000
AFIX   0
C3    1    0.471640    1.000906    0.019733    11.00000    0.02144    0.01910 =
         0.01307    0.00046   -0.00115    0.00784
C4    1    0.535486    0.829370   -0.040900    11.00000    0.06250    0.02723 =
         0.02633    0.00228    0.00338    0.03079
AFIX  23
H4A   2    0.597143    0.798684   -0.019990    11.00000   -1.20000
H4B   2    0.446075    0.753258   -0.036705    11.00000   -1.20000
AFIX   0
C5    1    0.562694    0.883331   -0.176058    11.00000    0.10636    0.04636 =
         0.03307    0.00103    0.02583    0.03229
AFIX  33
H5A   2    0.551850    0.814345   -0.233468    11.00000   -1.50000
H5B   2    0.652118    0.956826   -0.181800    11.00000   -1.50000
H5C   2    0.501247    0.912798   -0.198010    11.00000   -1.50000
AFIX   0
CU1   3    0.234337    0.758211    0.086173    11.00000    0.02016    0.01687 =
         0.02173    0.00155   -0.00139    0.00463
O1    4    0.587564    0.876541    0.264782    11.00000    0.02502    0.02699 =
         0.01875    0.00660    0.00291    0.01417
O2    4    0.376589    0.786846    0.206685    11.00000    0.01985    0.03082 =
         0.01904    0.00765   -0.00137    0.00641
O3    4    0.539150    1.121800   -0.006788    11.00000    0.02009    0.01435 =
         0.03323    0.00450   -0.00032    0.00868
O4    4    0.347078    0.934074    0.011735    11.00000    0.02985    0.02127 =
         0.02916    0.00856   -0.00097    0.00975
MOLE   1
O1W   4    0.122712    0.855339    0.178493    11.00000    0.04304    0.03946 =
         0.08173    0.00453    0.03369    0.01685
O2W   4    0.816460    0.894558    0.130175    10.50000    0.03172    0.08757 =
         0.08258    0.02241    0.00243    0.02940
O3W   4    0.082940    1.000504    0.386025    10.50000    0.07118    0.11625 =
         0.13635   -0.04469   -0.02330    0.04855
HKLF    4

REM  import in P 65
REM R1 =  0.0509 for    1813 Fo > 4sig(Fo)  and  0.0558 for all    1916 data
REM    120 parameters refined using      1 restraints

END

WGHT      0.0429      3.4126

REM Highest difference peak  0.721,  deepest hole -0.496,  1-sigma level  0.124
Q1    1   0.2314  0.7621  0.0053  11.00000  0.05    0.72
Q2    1   0.2390  0.7557  0.1650  11.00000  0.05    0.64
Q3    1   0.6407  0.9364 -0.0132  11.00000  0.05    0.55
Q4    1   0.6464  0.9141 -0.1421  11.00000  0.05    0.48
Q5    1   0.4566  1.1395 -0.0045  11.00000  0.05    0.48
Q6    1   0.3459  0.7765  0.1347  11.00000  0.05    0.45
Q7    1   0.2191  0.6800  0.1033  11.00000  0.05    0.44
Q8    1   0.2996  0.8596  0.0286  11.00000  0.05    0.43
Q9    1   0.1673  0.6934  0.0779  11.00000  0.05    0.42
Q10   1   0.2777  0.8364  0.0774  11.00000  0.05    0.41
Q11   1   0.1451  1.0069  0.4078  11.00000  0.05    0.41
Q12   1   0.1808  0.8014  0.0251  11.00000  0.05    0.41
Q13   1   0.5762  0.8503  0.3294  11.00000  0.05    0.40
Q14   1   0.3128  0.7939  0.0816  11.00000  0.05    0.40
Q15   1   0.8793  1.0159  0.1702  11.00000  0.05    0.38
Q16   1   0.5184  0.8774 -0.0022  11.00000  0.05    0.37
Q17   1   0.5724  0.8695  0.1945  11.00000  0.05    0.37
Q18   1   0.6535  0.8647  0.0285  11.00000  0.05    0.36
Q19   1   0.1705  1.0318  0.3326  11.00000  0.05    0.36
Q20   1   0.5562  1.0234  0.0775  11.00000  0.05    0.36
;
_shelx_res_checksum              71179


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_compound2
_database_code_depnum_ccdc_archive 'CCDC 1867352'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H8 Cu O5'
_chemical_formula_weight         211.65

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      Orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'C 2 c b'
_space_group_name_Hall           'C -2bc 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.770(3)
_cell_length_b                   9.921(3)
_cell_length_c                   14.477(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1403.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4038
_cell_measurement_theta_min      4.061
_cell_measurement_theta_max      27.491

_exptl_crystal_description       plate
_exptl_crystal_colour            blu
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.004
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    3.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.4187
_exptl_absorpt_correction_T_max  0.4290
_exptl_absorpt_correction_type   sphere
_exptl_crystal_size_rad          0.1900
_exptl_absorpt_process_details   
;
Interpolation using  Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'KappaCCD Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            4038
_diffrn_reflns_av_unetI/netI     0.0837
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.061
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1408
_reflns_number_gt                1058
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²+5.8957P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.43(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1408
_refine_ls_number_parameters     108
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.030
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3980(8) 0.3364(9) 0.3385(7) 0.021(2) Uani 1 1 d . . . . .
C2 C 0.3251(8) 0.2334(9) 0.3999(6) 0.018(2) Uani 1 1 d . . . . .
H2 H 0.3944 0.1666 0.4173 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2208(9) 0.1588(9) 0.3408(6) 0.0169(19) Uani 1 1 d . . . . .
C4 C 0.2708(10) 0.2906(10) 0.4890(7) 0.027(2) Uani 1 1 d . . . . .
H4A H 0.3383 0.3519 0.5145 0.032 Uiso 1 1 calc R U . . .
H4B H 0.1888 0.3423 0.4759 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2376(12) 0.1848(11) 0.5599(7) 0.035(3) Uani 1 1 d . . . . .
H5A H 0.1728 0.1221 0.5345 0.053 Uiso 1 1 calc R U . . .
H5B H 0.1991 0.2270 0.6136 0.053 Uiso 1 1 calc R U . . .
H5C H 0.3197 0.1377 0.5768 0.053 Uiso 1 1 calc R U . . .
Cu1 Cu 0.44644(14) 0.11040(8) 0.21818(6) 0.0173(3) Uani 1 1 d . . . . .
O1 O 0.3950(6) 0.4577(6) 0.3608(5) 0.0220(15) Uani 1 1 d . . . . .
O2 O 0.4612(8) 0.2926(5) 0.2671(4) 0.0214(14) Uani 1 1 d . . . . .
O3 O 0.0987(6) 0.1631(6) 0.3636(4) 0.0211(14) Uani 1 1 d . . . . .
O4 O 0.2631(6) 0.0950(6) 0.2715(5) 0.0255(16) Uani 1 1 d . . . . .
O1W O 0.5500(5) 0.0057(6) 0.3383(5) 0.0251(16) Uani 1 1 d D . . . .
H1W H 0.639(5) 0.033(7) 0.323(7) 0.038 Uiso 1 1 d D U . . .
H2W H 0.544(8) -0.087(4) 0.326(8) 0.038 Uiso 1 1 d D U . . .

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 0.016(4) 0.019(5) 0.028(5) 0.014(5) -0.013(4) -0.003(3)
C2 0.018(4) 0.020(5) 0.017(5) 0.004(4) -0.002(4) -0.009(4)
C3 0.015(5) 0.013(4) 0.022(5) 0.005(4) -0.005(4) -0.006(4)
C4 0.027(5) 0.022(5) 0.031(6) -0.003(5) 0.006(4) -0.006(4)
C5 0.036(6) 0.046(7) 0.023(6) -0.001(5) 0.003(5) 0.000(5)
Cu1 0.0124(4) 0.0129(4) 0.0267(5) -0.0004(5) 0.0001(8) -0.0020(8)
O1 0.021(3) 0.014(3) 0.031(4) 0.004(3) 0.003(2) -0.004(2)
O2 0.017(3) 0.019(3) 0.028(3) -0.002(2) 0.007(3) 0.000(4)
O3 0.007(3) 0.025(3) 0.031(4) -0.005(3) -0.003(3) -0.008(3)
O4 0.017(3) 0.027(4) 0.032(4) -0.009(3) 0.002(3) -0.009(3)
O1W 0.010(3) 0.021(4) 0.045(4) 0.000(3) -0.003(3) -0.001(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 1.246(11) . ?
C1 O2 1.280(11) . ?
C1 C2 1.531(12) . ?
C2 C4 1.505(13) . ?
C2 C3 1.522(12) . ?
C3 O3 1.238(10) . ?
C3 O4 1.257(11) . ?
C4 C5 1.504(14) . ?
Cu1 O2 1.947(5) . ?
Cu1 O4 1.956(6) . ?
Cu1 O1 1.963(6) 6_445 ?
Cu1 O3 1.972(6) 2 ?
Cu1 O1W 2.264(7) . ?
O1 Cu1 1.963(6) 6_455 ?
O3 Cu1 1.972(6) 2_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 O2 123.3(8) . . ?
O1 C1 C2 118.9(8) . . ?
O2 C1 C2 117.8(8) . . ?
C4 C2 C3 115.4(7) . . ?
C4 C2 C1 114.2(8) . . ?
C3 C2 C1 108.0(7) . . ?
O3 C3 O4 123.2(8) . . ?
O3 C3 C2 118.6(8) . . ?
O4 C3 C2 118.2(8) . . ?
C5 C4 C2 113.4(8) . . ?
O2 Cu1 O4 89.8(3) . . ?
O2 Cu1 O1 161.3(3) . 6_445 ?
O4 Cu1 O1 86.3(3) . 6_445 ?
O2 Cu1 O3 85.2(3) . 2 ?
O4 Cu1 O3 161.5(3) . 2 ?
O1 Cu1 O3 92.7(3) 6_445 2 ?
O2 Cu1 O1W 96.5(3) . . ?
O4 Cu1 O1W 94.0(3) . . ?
O1 Cu1 O1W 102.0(3) 6_445 . ?
O3 Cu1 O1W 104.2(2) 2 . ?
C1 O1 Cu1 126.0(6) . 6_455 ?
C1 O2 Cu1 125.0(6) . . ?
C3 O3 Cu1 123.9(6) . 2_455 ?
C3 O4 Cu1 125.2(5) . . ?

_refine_diff_density_max         1.040
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.130

_shelxl_version_number           2013-4

_shelx_res_file                  
;
TITL import in C 2 c b
CELL  0.71073   9.7700   9.9210  14.4770   90.000   90.000   90.000
ZERR     8.00   0.0030   0.0030   0.0030    0.000    0.000    0.000
LATT  -7
SYMM  1/2 + X,   Y, 1/2 - Z
SYMM    X, - Y, - Z
SYMM  1/2 + X, - Y, 1/2 + Z
SFAC  C    H    CU   O
UNIT  40   64   8    40
MERG   2
ACTA
OMIT     0   6   0
TWIN
DFIX   0.95  0.02  O1w H1w O1w H2w
DFIX   1.50  0.02  H1w H2w
FMAP   2
PLAN   20
L.S.  10
WGHT    0.027700    5.895700
BASF   0.43448
FVAR       0.35053
C1    1    0.397984    0.336432    0.338475    11.00000    0.01586    0.01935 =
         0.02796    0.01373   -0.01333   -0.00281
C2    1    0.325084    0.233370    0.399910    11.00000    0.01802    0.02035 =
         0.01692    0.00407   -0.00239   -0.00861
AFIX  13
H2    2    0.394418    0.166630    0.417264    11.00000   -1.20000
AFIX   0
C3    1    0.220752    0.158822    0.340818    11.00000    0.01473    0.01346 =
         0.02246    0.00544   -0.00514   -0.00590
C4    1    0.270841    0.290600    0.488972    11.00000    0.02679    0.02237 =
         0.03061   -0.00296    0.00609   -0.00600
AFIX  23
H4A   2    0.338324    0.351857    0.514527    11.00000   -1.20000
H4B   2    0.188817    0.342301    0.475939    11.00000   -1.20000
AFIX   0
C5    1    0.237633    0.184781    0.559876    11.00000    0.03648    0.04571 =
         0.02325   -0.00051    0.00297    0.00035
AFIX 137
H5A   2    0.172829    0.122146    0.534534    11.00000   -1.50000
H5B   2    0.199128    0.226957    0.613604    11.00000   -1.50000
H5C   2    0.319741    0.137681    0.576759    11.00000   -1.50000
AFIX   0
CU1   3    0.446441    0.110403    0.218181    11.00000    0.01242    0.01291 =
         0.02672   -0.00043    0.00008   -0.00198
O1    4    0.395012    0.457725    0.360834    11.00000    0.02087    0.01392 =
         0.03111    0.00436    0.00265   -0.00423
O2    4    0.461181    0.292641    0.267089    11.00000    0.01722    0.01880 =
         0.02815   -0.00203    0.00651   -0.00035
O3    4    0.098746    0.163090    0.363640    11.00000    0.00740    0.02477 =
         0.03119   -0.00503   -0.00314   -0.00827
O4    4    0.263143    0.094970    0.271464    11.00000    0.01747    0.02735 =
         0.03165   -0.00850    0.00217   -0.00872
MOLE    1
O1W   4    0.550025    0.005658    0.338292    11.00000    0.00972    0.02071 =
         0.04497    0.00028   -0.00327   -0.00132
H1W   2    0.638806    0.032740    0.323035    11.00000   -1.50000
H2W   2    0.544116   -0.086883    0.325695    11.00000   -1.50000
HKLF    4

REM  import in C 2 c b
REM R1 =  0.0458 for    1058 Fo > 4sig(Fo)  and  0.0759 for all    1408 data
REM    108 parameters refined using      4 restraints

END

WGHT      0.0277      5.8989

REM Highest difference peak  1.040,  deepest hole -0.732,  1-sigma level  0.130
Q1    1   0.4482  0.1095  0.2876  11.00000  0.05    1.04
Q2    1   0.4464  0.1084  0.1469  11.00000  0.05    1.01
Q3    1   0.4433  0.1101  0.3390  11.00000  0.05    0.70
Q4    1   0.3995  0.4505  0.2857  11.00000  0.05    0.47
Q5    1   0.4471  0.0495  0.2132  11.00000  0.05    0.46
Q6    1   0.4295  0.5176  0.3286  11.00000  0.05    0.45
Q7    1   0.3991  0.3070  0.2470  11.00000  0.05    0.44
Q8    1   0.4487  0.1887  0.4636  11.00000  0.05    0.42
Q9    1  -0.0465  0.1324  0.4052  11.00000  0.05    0.41
Q10   1   0.0651  0.1839  0.4343  11.00000  0.05    0.41
Q11   1   0.2611  0.2085  0.6229  11.00000  0.05    0.40
Q12   1   0.1788  0.2932  0.5128  11.00000  0.05    0.39
Q13   1   0.3225  0.0279  0.2160  11.00000  0.05    0.38
Q14   1   0.4493  0.1514  0.3993  11.00000  0.05    0.37
Q15   1   0.5113 -0.2036  0.3314  11.00000  0.05    0.37
Q16   1   0.4028  0.4282  0.5459  11.00000  0.05    0.36
Q17   1   0.4326  0.3395  0.2160  11.00000  0.05    0.36
Q18   1   0.0533  0.3137  0.5060  11.00000  0.05    0.36
Q19   1   0.1177  0.1618  0.2902  11.00000  0.05    0.36
Q20   1   0.2010  0.4495  0.5006  11.00000  0.05    0.35
;
_shelx_res_checksum              5874


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
_exptl_crystal_preparation       'Magnetic properties'
