# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_cu3(oac)2(eg)2
_database_code_depnum_ccdc_archive 'CCDC 1857785'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_cu3(oac)2(eg)2      
;
PROBLEM: Short Inter D...A Contact  O8       ..O8               2.71 Ang.
RESPONSE: Atom O8 is part of a planar Cu2O2 unit. The short distance is due to the bridging coordination mode of the alkoxide ligands (deprotonated ethylene glycol moecules).  
;

_audit_creation_date             2018-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H14 Cu3 O8'
_chemical_formula_sum            'C8 H14 Cu3 O8'
_chemical_formula_weight         428.81
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2381(6)
_cell_length_b                   8.3264(6)
_cell_length_c                   9.8035(7)
_cell_angle_alpha                85.166(3)
_cell_angle_beta                 83.523(3)
_cell_angle_gamma                75.803(2)
_cell_volume                     646.64(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1422
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      23.99
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.855
_exptl_absorpt_coefficient_mu    4.918
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0507 before and 0.0390 after correction. The Ratio of minimum to maximum transmission is 0.9248. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             426
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.033
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10600
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.094
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2031
_reflns_number_total             2936
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX3 v2017.3 (Bruker, USA, 2017)'
_computing_data_collection       'APEX3 v2017.3 (Bruker, USA, 2017)'
_computing_data_reduction        'APEX3 v2017.3 (Bruker, USA, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.029
_refine_diff_density_min         -0.722
_refine_diff_density_rms         0.181
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2936
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0250P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0781
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C3)
Uanis(C5) = Uanis(C6) = Uanis(C7) = Uanis(C8)
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C6(H6A,H6B), C5(H5A,H5B)
3.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cu2 Cu 0.46225(7) 0.83329(7) 0.61868(6) 0.00766(16) Uani 1 1 d . . . . .
Cu1 Cu 0.82520(8) 0.56413(7) 0.59173(6) 0.00729(16) Uani 1 1 d . . . . .
Cu3 Cu 0.13367(7) 0.65791(7) 0.65955(6) 0.00731(16) Uani 1 1 d . . . . .
O5 O 0.9629(4) 0.5408(4) 0.7446(3) 0.0070(7) Uani 1 1 d . . . . .
O8 O 0.0488(4) 0.6451(4) 0.4826(3) 0.0070(7) Uani 1 1 d . . . . .
O7 O 0.2530(4) 0.8137(4) 0.5612(3) 0.0091(8) Uani 1 1 d . . . . .
O2 O 0.5643(4) 0.8599(4) 0.4269(3) 0.0092(8) Uani 1 1 d . . . . .
O1 O 0.6936(4) 0.5904(4) 0.4285(3) 0.0095(8) Uani 1 1 d . . . . .
O3 O 0.3615(4) 0.8644(4) 0.8069(3) 0.0119(8) Uani 1 1 d . . . . .
O6 O 0.6826(4) 0.7525(4) 0.6784(3) 0.0160(9) Uani 1 1 d . . . . .
O4 O 0.1980(4) 0.6822(4) 0.8392(3) 0.0149(9) Uani 1 1 d . . . . .
C1 C 0.6415(6) 0.7313(6) 0.3644(5) 0.0090(8) Uani 1 1 d . . . . .
C8 C 0.0577(6) 0.7971(6) 0.4036(5) 0.0102(6) Uani 1 1 d . . . . .
H8A H -0.032644 0.890249 0.439021 0.012 Uiso 1 1 calc R . . . .
H8B H 0.044498 0.786790 0.305839 0.012 Uiso 1 1 calc R . . . .
C7 C 0.2281(6) 0.8276(6) 0.4178(5) 0.0102(6) Uani 1 1 d . . . . .
H7A H 0.317204 0.744968 0.367815 0.012 Uiso 1 1 calc R . . . .
H7B H 0.233540 0.939711 0.378183 0.012 Uiso 1 1 calc R . . . .
C6 C 0.7428(6) 0.7794(6) 0.8033(5) 0.0102(6) Uani 1 1 d . . . . .
H6A H 0.646920 0.819319 0.872362 0.012 Uiso 1 1 calc R . . . .
H6B H 0.809574 0.864315 0.786761 0.012 Uiso 1 1 calc R . . . .
C3 C 0.2633(6) 0.7908(6) 0.8795(5) 0.0090(8) Uani 1 1 d . . . . .
C2 C 0.6726(7) 0.7392(7) 0.2122(5) 0.0139(12) Uani 1 1 d . . . . .
H2A H 0.615851 0.849020 0.175021 0.021 Uiso 1 1 calc GR . . . .
H2B H 0.628679 0.654059 0.175498 0.021 Uiso 1 1 calc GR . . . .
H2C H 0.793794 0.719610 0.185506 0.021 Uiso 1 1 calc GR . . . .
C5 C 0.8516(6) 0.6158(6) 0.8557(5) 0.0102(6) Uani 1 1 d . . . . .
H5A H 0.917024 0.635530 0.928675 0.012 Uiso 1 1 calc R . . . .
H5B H 0.779512 0.540964 0.895320 0.012 Uiso 1 1 calc R . . . .
C4 C 0.2266(8) 0.8265(8) 1.0290(5) 0.0248(15) Uani 1 1 d . . . . .
H4A H 0.324834 0.772396 1.077960 0.037 Uiso 1 1 calc GR . . . .
H4B H 0.129620 0.783862 1.068457 0.037 Uiso 1 1 calc GR . . . .
H4C H 0.201437 0.946642 1.038182 0.037 Uiso 1 1 calc GR . . . .


_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
Cu2 O7 1.921(3) . ?
Cu2 O2 1.989(3) . ?
Cu2 O3 1.947(3) . ?
Cu2 O6 1.914(3) . ?
Cu1 Cu3 2.9919(8) 1_655 ?
Cu1 O5 1.948(3) . ?
Cu1 O8 2.244(3) 1_655 ?
Cu1 O8 1.949(3) 2_666 ?
Cu1 O1 2.000(3) . ?
Cu1 O6 1.912(3) . ?
Cu3 O5 1.974(3) 1_455 ?
Cu3 O8 1.962(3) . ?
Cu3 O7 1.944(3) . ?
Cu3 O1 2.372(3) 2_666 ?
Cu3 O4 1.936(3) . ?
O5 C5 1.423(6) . ?
O8 C8 1.440(5) . ?
O7 C7 1.434(5) . ?
O2 C1 1.271(6) . ?
O1 C1 1.283(5) . ?
O3 C3 1.256(5) . ?
O6 C6 1.427(5) . ?
O4 C3 1.268(6) . ?
C1 C2 1.484(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.510(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.520(6) . ?
C3 C4 1.503(7) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 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
O7 Cu2 O2 93.38(14) . . ?
O7 Cu2 O3 91.10(14) . . ?
O3 Cu2 O2 165.99(14) . . ?
O6 Cu2 O7 155.41(15) . . ?
O6 Cu2 O2 89.62(14) . . ?
O6 Cu2 O3 91.82(14) . . ?
O5 Cu1 Cu3 40.60(10) . 1_655 ?
O5 Cu1 O8 80.35(12) . 1_655 ?
O5 Cu1 O8 93.56(13) . 2_666 ?
O5 Cu1 O1 177.13(14) . . ?
O8 Cu1 Cu3 40.98(8) 1_655 1_655 ?
O8 Cu1 Cu3 93.66(10) 2_666 1_655 ?
O8 Cu1 O8 80.26(14) 2_666 1_655 ?
O8 Cu1 O1 85.55(13) 2_666 . ?
O1 Cu1 Cu3 136.68(10) . 1_655 ?
O1 Cu1 O8 96.81(13) . 1_655 ?
O6 Cu1 Cu3 91.44(11) . 1_655 ?
O6 Cu1 O5 86.59(13) . . ?
O6 Cu1 O8 107.29(14) . 1_655 ?
O6 Cu1 O8 172.34(16) . 2_666 ?
O6 Cu1 O1 94.65(14) . . ?
O5 Cu3 Cu1 39.98(9) 1_455 1_455 ?
O5 Cu3 O1 91.67(12) 1_455 2_666 ?
O8 Cu3 Cu1 48.60(10) . 1_455 ?
O8 Cu3 O5 87.19(13) . 1_455 ?
O8 Cu3 O1 75.82(12) . 2_666 ?
O7 Cu3 Cu1 129.15(9) . 1_455 ?
O7 Cu3 O5 165.69(13) . 1_455 ?
O7 Cu3 O8 85.45(13) . . ?
O7 Cu3 O1 98.39(13) . 2_666 ?
O1 Cu3 Cu1 90.80(8) 2_666 1_455 ?
O4 Cu3 Cu1 128.12(11) . 1_455 ?
O4 Cu3 O5 90.47(14) . 1_455 ?
O4 Cu3 O8 174.98(15) . . ?
O4 Cu3 O7 95.85(14) . . ?
O4 Cu3 O1 108.71(13) . 2_666 ?
Cu1 O5 Cu3 99.42(14) . 1_655 ?
C5 O5 Cu1 105.3(3) . . ?
C5 O5 Cu3 117.3(3) . 1_655 ?
Cu1 O8 Cu1 99.74(14) 2_666 1_455 ?
Cu1 O8 Cu3 106.90(15) 2_666 . ?
Cu3 O8 Cu1 90.43(12) . 1_455 ?
C8 O8 Cu1 118.4(3) . 2_666 ?
C8 O8 Cu1 129.9(3) . 1_455 ?
C8 O8 Cu3 106.6(3) . . ?
Cu2 O7 Cu3 120.10(16) . . ?
C7 O7 Cu2 120.2(3) . . ?
C7 O7 Cu3 110.4(3) . . ?
C1 O2 Cu2 119.1(3) . . ?
Cu1 O1 Cu3 91.49(12) . 2_666 ?
C1 O1 Cu1 122.5(3) . . ?
C1 O1 Cu3 128.7(3) . 2_666 ?
C3 O3 Cu2 130.4(3) . . ?
Cu1 O6 Cu2 117.20(17) . . ?
C6 O6 Cu2 128.7(3) . . ?
C6 O6 Cu1 111.5(3) . . ?
C3 O4 Cu3 130.0(3) . . ?
O2 C1 O1 122.2(4) . . ?
O2 C1 C2 120.5(4) . . ?
O1 C1 C2 117.3(4) . . ?
O8 C8 H8A 110.3 . . ?
O8 C8 H8B 110.3 . . ?
O8 C8 C7 106.9(4) . . ?
H8A C8 H8B 108.6 . . ?
C7 C8 H8A 110.3 . . ?
C7 C8 H8B 110.3 . . ?
O7 C7 C8 108.3(4) . . ?
O7 C7 H7A 110.0 . . ?
O7 C7 H7B 110.0 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
O6 C6 H6A 110.1 . . ?
O6 C6 H6B 110.1 . . ?
O6 C6 C5 108.1(4) . . ?
H6A C6 H6B 108.4 . . ?
C5 C6 H6A 110.1 . . ?
C5 C6 H6B 110.1 . . ?
O3 C3 O4 125.6(5) . . ?
O3 C3 C4 117.6(4) . . ?
O4 C3 C4 116.6(5) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O5 C5 C6 109.2(4) . . ?
O5 C5 H5A 109.8 . . ?
O5 C5 H5B 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
