# Electronic Supplementary Material (ESI) for ChemComm.
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1038935'
_audit_update_record             
;
2014-12-11 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        UTSA-60
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Cu2 N0 O10'
_chemical_formula_weight         517.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Imma

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

_cell_length_a                   18.8261(10)
_cell_length_b                   22.1934(9)
_cell_length_c                   10.0062(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4180.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.822
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    1.493
_exptl_absorpt_correction_type   ?
_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     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3292
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.98
_diffrn_reflns_theta_max         61.16
_reflns_number_total             1664
_reflns_number_gt                1165
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1030P)²+0.0000P] where P=(Fo²+2Fc²)/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         1664
_refine_ls_number_parameters     72
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.1700
_refine_ls_wR_factor_gt          0.1574
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.947
_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
Cu1 Cu 0.29546(4) 0.2500 0.15013(9) 0.0440(4) Uani 1 2 d S . .
O1 O 0.15621(15) 0.31186(12) 0.2455(4) 0.0610(9) Uani 1 1 d . . .
O2 O 0.23412(15) 0.31294(12) 0.0773(3) 0.0634(9) Uani 1 1 d . . .
O3 O 0.3702(3) 0.2500 -0.0101(7) 0.116(2) Uani 1 2 d SD . .
H3B H 0.3485 0.2500 -0.0849 0.174 Uiso 1 2 d SRD . .
H3C H 0.4149 0.2500 -0.0247 0.174 Uiso 1 2 d SRD . .
C1 C 0.1785(2) 0.33097(19) 0.1385(6) 0.0548(12) Uani 1 1 d . . .
C2 C 0.1398(2) 0.38204(18) 0.0716(5) 0.0624(13) Uani 1 1 d . . .
H2A H 0.1597 0.4007 -0.0028 0.075 Uiso 1 1 calc R . .
C3 C 0.0770(2) 0.40094(18) 0.1181(5) 0.0618(13) Uani 1 1 d . . .
H3A H 0.0576 0.3811 0.1914 0.074 Uiso 1 1 calc R . .
C4 C 0.0364(2) 0.45217(16) 0.0589(5) 0.0596(13) Uani 1 1 d . . .
C5 C 0.0722(3) 0.5000 0.0000 0.0623(18) Uani 1 2 d S . .
H5A H 0.1216 0.5000 0.0000 0.075 Uiso 1 2 calc SR . .

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
Cu1 0.0294(5) 0.0251(5) 0.0774(7) 0.000 -0.0069(4) 0.000
O1 0.0440(16) 0.0445(16) 0.095(2) 0.0138(19) -0.0032(18) 0.0120(14)
O2 0.0492(18) 0.0477(16) 0.093(2) 0.0167(18) -0.0036(17) 0.0125(14)
O3 0.089(4) 0.122(5) 0.136(5) 0.000 0.042(4) 0.000
C1 0.034(2) 0.030(2) 0.100(4) 0.007(3) -0.011(2) -0.0005(18)
C2 0.046(3) 0.037(2) 0.104(4) 0.030(3) -0.005(2) 0.0078(19)
C3 0.041(2) 0.034(2) 0.111(4) 0.023(3) -0.009(2) -0.0013(19)
C4 0.0331(19) 0.034(2) 0.112(4) 0.030(3) -0.002(2) -0.0009(17)
C5 0.036(3) 0.040(3) 0.110(5) 0.025(4) 0.000 0.000

_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 1.950(3) 7_545 ?
Cu1 O1 1.950(3) 13 ?
Cu1 O2 1.953(3) 11_565 ?
Cu1 O2 1.953(3) . ?
Cu1 O3 2.132(6) . ?
Cu1 Cu1 2.6313(17) 13 ?
O1 C1 1.227(5) . ?
O1 Cu1 1.950(3) 13 ?
O2 C1 1.277(6) . ?
O3 H3B 0.8527 . ?
O3 H3C 0.8541 . ?
C1 C2 1.505(6) . ?
C2 C3 1.338(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.493(5) . ?
C3 H3A 0.9300 . ?
C4 C4 1.371(8) 12 ?
C4 C5 1.389(4) . ?
C5 C4 1.389(4) 4_565 ?
C5 H5A 0.9300 . ?

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 89.50(18) 7_545 13 ?
O1 Cu1 O2 168.25(15) 7_545 11_565 ?
O1 Cu1 O2 88.41(13) 13 11_565 ?
O1 Cu1 O2 88.41(13) 7_545 . ?
O1 Cu1 O2 168.25(15) 13 . ?
O2 Cu1 O2 91.30(18) 11_565 . ?
O1 Cu1 O3 95.44(17) 7_545 . ?
O1 Cu1 O3 95.44(17) 13 . ?
O2 Cu1 O3 96.28(16) 11_565 . ?
O2 Cu1 O3 96.28(16) . . ?
O1 Cu1 Cu1 84.08(10) 7_545 13 ?
O1 Cu1 Cu1 84.08(10) 13 13 ?
O2 Cu1 Cu1 84.20(10) 11_565 13 ?
O2 Cu1 Cu1 84.20(10) . 13 ?
O3 Cu1 Cu1 179.3(2) . 13 ?
C1 O1 Cu1 123.5(3) . 13 ?
C1 O2 Cu1 122.0(3) . . ?
Cu1 O3 H3B 110.2 . . ?
Cu1 O3 H3C 141.1 . . ?
H3B O3 H3C 108.7 . . ?
O1 C1 O2 126.2(4) . . ?
O1 C1 C2 118.9(4) . . ?
O2 C1 C2 114.8(5) . . ?
C3 C2 C1 120.6(5) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 123.5(4) . . ?
C2 C3 H3A 118.2 . . ?
C4 C3 H3A 118.2 . . ?
C4 C4 C5 119.0(2) 12 . ?
C4 C4 C3 120.8(2) 12 . ?
C5 C4 C3 120.2(3) . . ?
C4 C5 C4 121.9(5) . 4_565 ?
C4 C5 H5A 119.0 . . ?
C4 C5 H5A 119.0 4_565 . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        61.16
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.568
_refine_diff_density_min         -1.958
_refine_diff_density_rms         0.085

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.019 0.212 -0.311 2696 184 ' '
_platon_squeeze_details          
;
;


