# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Peter Tasker'
_publ_contact_author_email       PETER.TASKER@ED.AC.UK

_publ_section_title              
;
Polyacidic multiloading metal extractants.
;
loop_
_publ_author_name
'Peter Tasker'
'John Campbell'
'Ross Gordon'
'David K Henderson'
'Dorothy C R Henry'
;
R.M.Swart
;
'Fraser White'
'Jenny L. Wood'
'Lesley Yellowlees'

# Attachment 'ESI CIF figure4.cif'

data_pt7052
_database_code_depnum_ccdc_archive 'CCDC 692604'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_compound_source        'Ross Gordon'
_exptl_crystal_recrystallization_method 'Evaporation of chloroform solution'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '[Cu2 2(C13 H16 N2 O2)], 2(C H Cl3)'
_chemical_formula_sum            'C28 H34 Cl6 Cu2 N4 O4'
_chemical_formula_weight         830.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9794(3)
_cell_length_b                   9.9352(5)
_cell_length_c                   15.3792(9)
_cell_angle_alpha                98.853(4)
_cell_angle_beta                 94.933(4)
_cell_angle_gamma                103.343(4)
_cell_volume                     871.33(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             422
_exptl_absorpt_coefficient_mu    1.719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6911
_exptl_absorpt_correction_T_max  0.9318
_exptl_absorpt_process_details   'SADABS 2007/2'
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'Sphere (Omega Scans)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8149
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0761
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3052
_reflns_number_gt                2750
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'Shelxs Sheldrick'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Shelxp
_computing_publication_material  'Platon, encifer'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

>>> The Following ALERTS were generated <<<
#------------------------------------------
Format: alert-number_ALERT_alert-type_alert-level text

220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.67 Ratio
222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.08 Ratio
213_ALERT_2_C Atom C41 has ADP max/min Ratio ............. 3.70 oblat
250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.58
341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12

The model is complete and looks reasonable. I suspect most of these are
due to a combination of the crystal having been a needle containing copper,
which has led to some absorption effects and the generally weak dataset
which has an average I/s of 9.15.

242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C26
244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C1S

C26 is the pivot atom in a tBu group
C1S is the pivot atom in a CHCl3

911_ALERT_3_B # Missing FCF Refl Between THmin & STh/L= 0.595 19

Please see statistics below.

#==============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#==============================================================================
Theta sin(th)/Lambda Complete Expected Measured Missing
#------------------------------------------------------------------------------
20.82 0.500 1.000 1812 1812 0
23.01 0.550 0.998 2428 2423 5
25.03 0.595 0.994 3071 3052 19
#----------------------------------------------------------- ACTA Min. Res. ---

042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?

The reported formula is intended to make a little more chemical sense.

125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?

154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg.

The su's have not been manually altered and are those reported by Saint after
cell refinement.

764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.17 Ratio

Shelx is reporting too many Cu-X bonds

794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.18

Consistent with expected.

860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 7

These are DELU restraints
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+6.3537P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3052
_refine_ls_number_parameters     199
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0957
_refine_ls_wR_factor_ref         0.2094
_refine_ls_wR_factor_gt          0.2042
_refine_ls_goodness_of_fit_ref   1.303
_refine_ls_restrained_S_all      1.302
_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 0.96492(17) 0.45148(9) -0.09742(6) 0.0186(3) Uani 1 1 d . . .
O1 O 0.8521(9) 0.5706(5) -0.0055(4) 0.0225(13) Uani 1 1 d . . .
C1 C 0.6819(13) 0.6415(7) -0.0099(5) 0.0185(16) Uani 1 1 d . . .
C2 C 0.6279(14) 0.7136(8) 0.0681(5) 0.0213(17) Uani 1 1 d . . .
C3 C 0.4516(13) 0.7887(8) 0.0619(5) 0.0204(17) Uani 1 1 d . . .
H3 H 0.4093 0.8344 0.1146 0.024 Uiso 1 1 calc R . .
C4 C 0.3421(14) 0.7958(8) -0.0190(6) 0.0222(17) Uani 1 1 d U . .
C5 C 0.3964(14) 0.7206(8) -0.0956(5) 0.0239(18) Uani 1 1 d . . .
H5 H 0.3167 0.7208 -0.1517 0.029 Uiso 1 1 calc R . .
C6 C 0.5654(14) 0.6456(8) -0.0907(6) 0.0234(18) Uani 1 1 d . . .
H6 H 0.6012 0.5964 -0.1436 0.028 Uiso 1 1 calc R . .
C21 C 0.7338(15) 0.7241(8) 0.1560(6) 0.0255(19) Uani 1 1 d . . .
H21 H 0.6774 0.7750 0.2030 0.031 Uiso 1 1 calc R . .
N22 N 0.9039(12) 0.6680(7) 0.1759(5) 0.0248(16) Uani 1 1 d . . .
N23 N 0.9939(12) 0.6869(7) 0.2659(4) 0.0228(15) Uani 1 1 d U . .
C24 C 1.1462(14) 0.6075(8) 0.2724(6) 0.0251(18) Uani 1 1 d U . .
O25 O 1.1948(11) 0.5323(6) 0.2066(4) 0.0316(14) Uani 1 1 d U . .
C26 C 1.2403(14) 0.5969(9) 0.3640(6) 0.0253(18) Uani 1 1 d U . .
C27 C 1.497(2) 0.6023(16) 0.3669(7) 0.065(4) Uani 1 1 d . . .
H27A H 1.5595 0.5963 0.4269 0.098 Uiso 1 1 calc R . .
H27B H 1.5791 0.6909 0.3512 0.098 Uiso 1 1 calc R . .
H27C H 1.5183 0.5231 0.3246 0.098 Uiso 1 1 calc R . .
C28 C 1.2043(18) 0.7106(10) 0.4369(6) 0.040(2) Uani 1 1 d . . .
H28A H 1.2711 0.6979 0.4946 0.060 Uiso 1 1 calc R . .
H28B H 1.0381 0.7033 0.4372 0.060 Uiso 1 1 calc R . .
H28C H 1.2806 0.8036 0.4255 0.060 Uiso 1 1 calc R . .
C29 C 1.105(2) 0.4515(10) 0.3803(7) 0.049(3) Uani 1 1 d . . .
H29A H 1.1591 0.4381 0.4396 0.074 Uiso 1 1 calc R . .
H29B H 1.1318 0.3771 0.3356 0.074 Uiso 1 1 calc R . .
H29C H 0.9392 0.4476 0.3759 0.074 Uiso 1 1 calc R . .
C41 C 0.1625(15) 0.8824(8) -0.0245(6) 0.030(2) Uani 1 1 d U . .
H41A H 0.1012 0.8749 -0.0868 0.044 Uiso 1 1 calc R . .
H41B H 0.2354 0.9811 0.0009 0.044 Uiso 1 1 calc R . .
H41C H 0.0356 0.8468 0.0087 0.044 Uiso 1 1 calc R . .
Cl1S Cl -0.2146(5) 0.0521(3) 0.3310(2) 0.0631(9) Uani 1 1 d . . .
Cl2S Cl 0.2392(5) 0.1060(3) 0.43023(19) 0.0538(8) Uani 1 1 d . . .
Cl3S Cl 0.1928(6) 0.0699(3) 0.2402(2) 0.0593(8) Uani 1 1 d . . .
C1S C 0.0631(17) 0.0188(10) 0.3324(7) 0.038(2) Uani 1 1 d . . .
H1S H 0.0456 -0.0846 0.3288 0.045 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
Cu1 0.0219(5) 0.0128(5) 0.0244(5) 0.0039(4) -0.0009(4) 0.0116(4)
O1 0.022(3) 0.012(3) 0.037(3) 0.006(2) -0.001(3) 0.010(2)
C1 0.016(4) 0.012(3) 0.027(4) 0.003(3) -0.004(3) 0.006(3)
C2 0.021(4) 0.012(4) 0.030(4) 0.004(3) -0.002(3) 0.004(3)
C3 0.019(4) 0.015(4) 0.028(4) 0.002(3) 0.000(3) 0.008(3)
C4 0.021(4) 0.013(4) 0.037(5) 0.011(3) 0.003(4) 0.009(3)
C5 0.027(4) 0.023(4) 0.024(4) 0.005(3) -0.004(3) 0.013(3)
C6 0.026(4) 0.016(4) 0.030(4) 0.007(3) -0.006(4) 0.009(3)
C21 0.035(5) 0.010(4) 0.030(5) 0.000(3) -0.007(4) 0.008(3)
N22 0.028(4) 0.013(3) 0.033(4) 0.000(3) -0.005(3) 0.009(3)
N23 0.026(4) 0.018(3) 0.029(4) 0.007(3) -0.001(3) 0.012(3)
C24 0.023(4) 0.020(4) 0.040(5) 0.008(4) 0.006(4) 0.018(3)
O25 0.041(4) 0.037(3) 0.026(3) 0.006(3) 0.000(3) 0.029(3)
C26 0.025(4) 0.029(4) 0.027(4) 0.010(4) 0.005(3) 0.013(4)
C27 0.054(8) 0.118(12) 0.038(6) 0.011(7) -0.007(5) 0.055(8)
C28 0.047(6) 0.031(5) 0.041(6) 0.007(4) -0.007(5) 0.012(4)
C29 0.080(8) 0.024(5) 0.042(6) 0.011(4) -0.003(6) 0.011(5)
C41 0.029(5) 0.011(4) 0.055(6) 0.011(4) 0.006(4) 0.013(3)
Cl1S 0.0433(16) 0.0391(15) 0.102(3) -0.0089(15) -0.0027(16) 0.0193(12)
Cl2S 0.0647(19) 0.0289(13) 0.0599(17) -0.0017(12) -0.0137(14) 0.0099(12)
Cl3S 0.072(2) 0.0509(16) 0.0574(18) 0.0117(14) 0.0066(15) 0.0206(15)
C1S 0.040(6) 0.027(5) 0.049(6) 0.007(4) 0.003(5) 0.015(4)

_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 N22 1.906(7) 2_765 ?
Cu1 O25 1.906(6) 2_765 ?
Cu1 O1 1.916(5) 2_765 ?
Cu1 O1 1.967(5) . ?
Cu1 Cu1 2.965(2) 2_765 ?
O1 C1 1.368(9) . ?
O1 Cu1 1.916(5) 2_765 ?
C1 C6 1.382(10) . ?
C1 C2 1.402(11) . ?
C2 C21 1.420(11) . ?
C2 C3 1.430(10) . ?
C3 C4 1.375(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(11) . ?
C4 C41 1.528(10) . ?
C5 C6 1.391(11) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C21 N22 1.303(10) . ?
C21 H21 0.9500 . ?
N22 N23 1.410(9) . ?
N22 Cu1 1.906(7) 2_765 ?
N23 C24 1.342(9) . ?
C24 O25 1.259(10) . ?
C24 C26 1.500(12) . ?
O25 Cu1 1.906(6) 2_765 ?
C26 C27 1.521(13) . ?
C26 C28 1.531(12) . ?
C26 C29 1.552(13) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
Cl1S C1S 1.766(10) . ?
Cl2S C1S 1.740(10) . ?
Cl3S C1S 1.760(11) . ?
C1S H1S 1.0000 . ?

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
N22 Cu1 O25 81.6(3) 2_765 2_765 ?
N22 Cu1 O1 93.1(3) 2_765 2_765 ?
O25 Cu1 O1 174.3(2) 2_765 2_765 ?
N22 Cu1 O1 173.5(3) 2_765 . ?
O25 Cu1 O1 104.9(2) 2_765 . ?
O1 Cu1 O1 80.4(2) 2_765 . ?
N22 Cu1 Cu1 134.0(2) 2_765 2_765 ?
O25 Cu1 Cu1 144.40(17) 2_765 2_765 ?
O1 Cu1 Cu1 40.86(16) 2_765 2_765 ?
O1 Cu1 Cu1 39.58(15) . 2_765 ?
C1 O1 Cu1 128.5(5) . 2_765 ?
C1 O1 Cu1 131.8(5) . . ?
Cu1 O1 Cu1 99.6(2) 2_765 . ?
O1 C1 C6 120.7(7) . . ?
O1 C1 C2 119.8(7) . . ?
C6 C1 C2 119.4(7) . . ?
C1 C2 C21 127.0(7) . . ?
C1 C2 C3 118.9(7) . . ?
C21 C2 C3 114.1(7) . . ?
C4 C3 C2 121.2(7) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 118.5(7) . . ?
C3 C4 C41 120.4(8) . . ?
C5 C4 C41 121.0(7) . . ?
C6 C5 C4 120.9(7) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 120.9(8) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
N22 C21 C2 123.9(8) . . ?
N22 C21 H21 118.0 . . ?
C2 C21 H21 118.0 . . ?
C21 N22 N23 118.1(7) . . ?
C21 N22 Cu1 127.4(6) . 2_765 ?
N23 N22 Cu1 114.3(5) . 2_765 ?
C24 N23 N22 108.2(6) . . ?
O25 C24 N23 123.3(8) . . ?
O25 C24 C26 119.2(7) . . ?
N23 C24 C26 117.1(7) . . ?
C24 O25 Cu1 112.4(5) . 2_765 ?
C24 C26 C27 109.3(8) . . ?
C24 C26 C28 113.9(7) . . ?
C27 C26 C28 109.6(8) . . ?
C24 C26 C29 105.5(7) . . ?
C27 C26 C29 110.0(9) . . ?
C28 C26 C29 108.4(8) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
Cl2S C1S Cl3S 110.1(6) . . ?
Cl2S C1S Cl1S 110.9(5) . . ?
Cl3S C1S Cl1S 110.3(5) . . ?
Cl2S C1S H1S 108.4 . . ?
Cl3S C1S H1S 108.4 . . ?
Cl1S C1S H1S 108.4 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.053
_refine_diff_density_min         -1.163
_refine_diff_density_rms         0.150

# Attachment 'ESI CIF figure5.cif'

data_pt6032
_database_code_depnum_ccdc_archive 'CCDC 692605'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H38 Cu2 N2 O8'
_chemical_formula_sum            'C38 H38 Cu2 N2 O8'
_chemical_formula_weight         777.82

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8829(7)
_cell_length_b                   9.6493(10)
_cell_length_c                   12.3771(12)
_cell_angle_alpha                88.498(6)
_cell_angle_beta                 83.850(6)
_cell_angle_gamma                83.339(6)
_cell_volume                     811.70(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    717
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      26.5

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             402
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.04
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'TWINABS version 1.05'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       Sphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3802
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3802
_reflns_number_gt                3091
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Smart
_computing_cell_refinement       Saint
_computing_data_reduction        Saint
_computing_structure_solution    'Shelxs Sheldrick'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Shelxp
_computing_publication_material  Platon

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 23.01 Deg.
911_ALERT_3_B # Missing FCF Refl Between THmin & STh/l= 0.600 150
912_ALERT_3_C # Missing FCF Reflections Above STH/L=0.6 ...... 64

Data collection strategy was a sphere and the crystal is triclinic, and
twinned.
Twin law
-0.99434 -0.00064 -0.02085
0.00755 -0.99936 -0.01644
-0.43677 -0.05385 0.99478

061_ALERT_3_A Tmax/Tmin Range Test RR' too Large ............. 0.08

The crystal is a very thin plate, measuring its minimum dimension is very
difficult. However twinabs absorption correction should compensate for
this.

021_ALERT_1_B Ratio Unique / Expected Reflections too High ... 1.15
030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ?

MERG 0 was used as this crystal is a twin and was refined with HKLF5 data.

220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio

This carbon belongs to a tBu group which has high thermal motion.

341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 13

This is a consequence of the low completeness of data at high angle.

The crystal was twinned which was treated during integration. The batch scale
factor refines to 0.4 indicating a 60:40 twin. All hydrogen atoms were placed
geometrically as the data were of insufficient quality to find or refine them.
All non hydrogen atoms were refined anisotropically.

041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio

The formula calculated is incorrect and only contains half of the molecule
Formula, formula weight and Z have been corrected.

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1222P)^2^+4.5068P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3802
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0865
_refine_ls_wR_factor_ref         0.2302
_refine_ls_wR_factor_gt          0.2206
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.35629(18) -0.10457(12) 0.03923(10) 0.0168(3) Uani 1 1 d . . .
O1 O 0.5860(10) -0.0259(6) 0.0802(5) 0.0188(14) Uani 1 1 d . . .
N7 N 0.3730(10) -0.2087(7) 0.1743(6) 0.0127(15) Uani 1 1 d . . .
O11 O 0.1217(9) -0.1755(6) 0.0088(5) 0.0204(15) Uani 1 1 d . . .
O14 O -0.1471(10) -0.1471(7) -0.1158(6) 0.0305(17) Uani 1 1 d . . .
H14A H -0.0463 -0.1379 -0.0852 0.046 Uiso 1 1 calc R . .
O15 O -0.3894(10) -0.2793(7) -0.0924(6) 0.0311(17) Uani 1 1 d . . .
C2 C 0.6299(13) -0.0664(9) 0.1817(7) 0.0178(19) Uani 1 1 d . . .
C3 C 0.5246(13) -0.1692(9) 0.2329(7) 0.0155(18) Uani 1 1 d . . .
C8 C 0.2686(13) -0.3077(10) 0.2038(7) 0.021(2) Uani 1 1 d . . .
H8A H 0.3032 -0.3603 0.2663 0.025 Uiso 1 1 calc R . .
C9 C 0.1087(14) -0.3475(9) 0.1544(7) 0.0170(19) Uani 1 1 d . . .
C10 C 0.0358(13) -0.2777(8) 0.0603(7) 0.0166(19) Uani 1 1 d . . .
C12 C -0.1373(13) -0.3208(9) 0.0257(7) 0.0185(19) Uani 1 1 d . . .
C13 C -0.2389(13) -0.2497(9) -0.0669(7) 0.020(2) Uani 1 1 d . . .
C16 C -0.2269(14) -0.4269(9) 0.0792(8) 0.023(2) Uani 1 1 d . . .
H16A H -0.3430 -0.4522 0.0536 0.028 Uiso 1 1 calc R . .
C17 C -0.1570(14) -0.5001(10) 0.1695(7) 0.020(2) Uani 1 1 d . . .
C19 C 0.0102(14) -0.4566(9) 0.2031(7) 0.019(2) Uani 1 1 d . . .
H19A H 0.0628 -0.5039 0.2636 0.023 Uiso 1 1 calc R . .
C18 C -0.2634(16) -0.6098(11) 0.2270(8) 0.028(2) Uani 1 1 d . . .
H18A H -0.1916 -0.6482 0.2873 0.043 Uiso 1 1 calc R . .
H18B H -0.2733 -0.6844 0.1763 0.043 Uiso 1 1 calc R . .
H18C H -0.3956 -0.5694 0.2554 0.043 Uiso 1 1 calc R . .
C4 C 0.5675(13) -0.2221(9) 0.3350(7) 0.0176(19) Uani 1 1 d . . .
H4A H 0.4947 -0.2919 0.3693 0.021 Uiso 1 1 calc R . .
C5 C 0.7146(14) -0.1741(9) 0.3868(7) 0.018(2) Uani 1 1 d . . .
C6 C 0.8159(14) -0.0700(9) 0.3351(7) 0.022(2) Uani 1 1 d . . .
H6A H 0.9160 -0.0346 0.3698 0.026 Uiso 1 1 calc R . .
C7 C 0.7736(13) -0.0167(10) 0.2336(7) 0.020(2) Uani 1 1 d . . .
H7A H 0.8446 0.0545 0.2001 0.024 Uiso 1 1 calc R . .
C51 C 0.7653(14) -0.2276(10) 0.5010(7) 0.022(2) Uani 1 1 d . . .
C53 C 0.7184(17) -0.1095(12) 0.5817(7) 0.033(2) Uani 1 1 d . . .
H53A H 0.7505 -0.1436 0.6537 0.049 Uiso 1 1 calc R . .
H53B H 0.5781 -0.0754 0.5853 0.049 Uiso 1 1 calc R . .
H53C H 0.7964 -0.0333 0.5582 0.049 Uiso 1 1 calc R . .
C54 C 0.9852(15) -0.2794(11) 0.4946(8) 0.031(2) Uani 1 1 d . . .
H54A H 1.0185 -0.3134 0.5664 0.046 Uiso 1 1 calc R . .
H54B H 1.0618 -0.2025 0.4710 0.046 Uiso 1 1 calc R . .
H54C H 1.0159 -0.3554 0.4424 0.046 Uiso 1 1 calc R . .
C52 C 0.6523(17) -0.3490(12) 0.5392(9) 0.039(3) Uani 1 1 d . . .
H52A H 0.6869 -0.3807 0.6113 0.059 Uiso 1 1 calc R . .
H52B H 0.6862 -0.4258 0.4878 0.059 Uiso 1 1 calc R . .
H52C H 0.5108 -0.3190 0.5431 0.059 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
Cu1 0.0175(5) 0.0211(6) 0.0128(5) 0.0072(5) -0.0053(5) -0.0045(4)
O1 0.027(4) 0.017(3) 0.014(3) 0.006(3) -0.004(3) -0.007(3)
N7 0.013(4) 0.011(4) 0.015(4) -0.004(3) 0.001(3) -0.006(3)
O11 0.013(3) 0.023(3) 0.024(4) 0.006(3) -0.005(3) 0.000(3)
O14 0.018(4) 0.043(4) 0.032(4) 0.010(3) -0.008(3) -0.005(3)
O15 0.021(4) 0.028(4) 0.048(4) 0.006(3) -0.022(3) -0.006(3)
C2 0.015(5) 0.021(5) 0.015(4) 0.003(4) -0.001(4) 0.005(4)
C3 0.014(5) 0.012(4) 0.018(4) -0.002(3) 0.001(4) 0.006(3)
C8 0.016(5) 0.028(5) 0.019(5) 0.003(4) -0.003(4) -0.003(4)
C9 0.020(5) 0.020(5) 0.010(4) 0.000(4) -0.006(4) 0.003(4)
C10 0.022(5) 0.011(4) 0.017(5) -0.002(3) 0.006(4) -0.009(4)
C12 0.021(5) 0.017(4) 0.015(4) -0.005(4) 0.002(4) 0.006(4)
C13 0.017(5) 0.015(5) 0.028(5) -0.009(4) 0.005(4) -0.004(4)
C16 0.016(5) 0.020(5) 0.034(6) -0.015(4) 0.000(4) -0.004(4)
C17 0.018(5) 0.022(5) 0.019(5) -0.010(4) 0.002(4) 0.001(4)
C19 0.026(5) 0.018(5) 0.014(4) -0.003(4) -0.004(4) 0.001(4)
C18 0.030(6) 0.033(6) 0.024(5) -0.002(4) -0.001(4) -0.011(5)
C4 0.011(5) 0.020(5) 0.021(5) 0.004(4) -0.007(4) 0.004(4)
C5 0.019(5) 0.020(5) 0.015(4) 0.004(4) -0.001(4) 0.002(4)
C6 0.029(6) 0.017(5) 0.020(5) 0.001(4) -0.013(4) -0.001(4)
C7 0.011(5) 0.026(5) 0.023(5) 0.005(4) 0.002(4) -0.007(4)
C51 0.027(5) 0.025(5) 0.014(4) 0.006(4) -0.007(4) 0.002(4)
C53 0.037(6) 0.046(7) 0.012(4) -0.008(5) -0.006(4) 0.011(5)
C54 0.029(6) 0.036(6) 0.029(5) 0.013(5) -0.014(5) -0.002(5)
C52 0.042(7) 0.045(7) 0.036(6) 0.024(5) -0.023(5) -0.018(5)

_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 O11 1.902(7) . ?
Cu1 N7 1.936(7) . ?
Cu1 O1 1.950(7) . ?
Cu1 O1 1.955(6) 2_655 ?
Cu1 Cu1 3.056(2) 2_655 ?
O1 C2 1.360(10) . ?
O1 Cu1 1.955(6) 2_655 ?
N7 C8 1.283(11) . ?
N7 C3 1.424(11) . ?
O11 C10 1.323(10) . ?
O14 C13 1.333(11) . ?
O14 H14A 0.8400 . ?
O15 C13 1.183(11) . ?
C2 C7 1.373(13) . ?
C2 C3 1.396(12) . ?
C3 C4 1.399(12) . ?
C8 C9 1.410(13) . ?
C8 H8A 0.9500 . ?
C9 C19 1.406(13) . ?
C9 C10 1.438(12) . ?
C10 C12 1.418(13) . ?
C12 C16 1.375(13) . ?
C12 C13 1.514(13) . ?
C16 C17 1.405(14) . ?
C16 H16A 0.9500 . ?
C17 C19 1.377(13) . ?
C17 C18 1.480(13) . ?
C19 H19A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C4 C5 1.383(13) . ?
C4 H4A 0.9500 . ?
C5 C6 1.392(12) . ?
C5 C51 1.553(12) . ?
C6 C7 1.392(12) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C51 C52 1.518(14) . ?
C51 C53 1.518(13) . ?
C51 C54 1.532(13) . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 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
O11 Cu1 N7 94.1(3) . . ?
O11 Cu1 O1 175.8(3) . . ?
N7 Cu1 O1 83.9(3) . . ?
O11 Cu1 O1 105.0(3) . 2_655 ?
N7 Cu1 O1 160.9(3) . 2_655 ?
O1 Cu1 O1 77.0(3) . 2_655 ?
O11 Cu1 Cu1 143.3(2) . 2_655 ?
N7 Cu1 Cu1 122.4(2) . 2_655 ?
O1 Cu1 Cu1 38.54(16) . 2_655 ?
O1 Cu1 Cu1 38.43(19) 2_655 2_655 ?
C2 O1 Cu1 112.7(6) . . ?
C2 O1 Cu1 143.6(6) . 2_655 ?
Cu1 O1 Cu1 103.0(3) . 2_655 ?
C8 N7 C3 124.2(8) . . ?
C8 N7 Cu1 123.9(6) . . ?
C3 N7 Cu1 111.8(5) . . ?
C10 O11 Cu1 127.6(6) . . ?
C13 O14 H14A 109.5 . . ?
O1 C2 C7 124.4(8) . . ?
O1 C2 C3 116.5(8) . . ?
C7 C2 C3 119.1(8) . . ?
C2 C3 C4 120.2(9) . . ?
C2 C3 N7 114.5(8) . . ?
C4 C3 N7 125.2(8) . . ?
N7 C8 C9 127.6(9) . . ?
N7 C8 H8A 116.2 . . ?
C9 C8 H8A 116.2 . . ?
C19 C9 C8 118.0(8) . . ?
C19 C9 C10 118.6(9) . . ?
C8 C9 C10 123.3(8) . . ?
O11 C10 C12 120.7(8) . . ?
O11 C10 C9 122.4(8) . . ?
C12 C10 C9 117.0(8) . . ?
C16 C12 C10 120.7(8) . . ?
C16 C12 C13 116.5(8) . . ?
C10 C12 C13 122.7(8) . . ?
O15 C13 O14 122.4(9) . . ?
O15 C13 C12 123.4(8) . . ?
O14 C13 C12 114.2(8) . . ?
C12 C16 C17 123.9(9) . . ?
C12 C16 H16A 118.0 . . ?
C17 C16 H16A 118.0 . . ?
C19 C17 C16 114.9(9) . . ?
C19 C17 C18 123.2(9) . . ?
C16 C17 C18 121.8(9) . . ?
C17 C19 C9 124.8(9) . . ?
C17 C19 H19A 117.6 . . ?
C9 C19 H19A 117.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C5 C4 C3 120.9(9) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 118.0(8) . . ?
C4 C5 C51 122.8(8) . . ?
C6 C5 C51 119.2(9) . . ?
C7 C6 C5 121.4(9) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C2 C7 C6 120.4(8) . . ?
C2 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C52 C51 C53 110.0(9) . . ?
C52 C51 C54 107.8(8) . . ?
C53 C51 C54 109.3(9) . . ?
C52 C51 C5 111.2(8) . . ?
C53 C51 C5 109.7(7) . . ?
C54 C51 C5 108.9(8) . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C51 C54 H54A 109.5 . . ?
C51 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C51 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.935
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.935
_refine_diff_density_max         1.820
_refine_diff_density_min         -1.073
_refine_diff_density_rms         0.196
_chemical_compound_source        'Ross Gordon'
_exptl_crystal_recrystallization_method 'Evaporation of reaction mixture (MeOH)'