# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
O.Hietsoi
C.Dubceac
A.S.Filatov
M.A.Petrukhina
_publ_contact_author_name        'Petrukhina, Marina'
_publ_contact_author_email       marina@albany.edu

data_814791
_database_code_depnum_ccdc_archive 'CCDC 814791'
#TrackingRef '- 814791-revised.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2,4,6-triisopropylbenzoato-O,O'-copper(I)
;
_chemical_name_common            2,4,6-triisopropylbenzoato-O,O'-copper(i)
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H23 Cu O2'
_chemical_formula_sum            'C16 H23 Cu O2'
_chemical_formula_weight         310.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc '
_symmetry_int_tables_number      14

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

_cell_length_a                   17.979(3)
_cell_length_b                   5.7850(10)
_cell_length_c                   15.146(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.285(3)
_cell_angle_gamma                90.00
_cell_volume                     1526.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5507
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.03

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    1.426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (Bruker-AXS, 2003)
;
_exptl_absorpt_correction_T_min  0.6994
_exptl_absorpt_correction_T_max  0.9859

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.30\% \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10313
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2688
_reflns_number_gt                2214
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_cell_refinement       'SAINT Ver. 6.22 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'

_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.

Disorder of two isopropyl groups was modeled over two
orientations with a 1:1 ratio.
Disordered parts were restrained to be similar with the SAME command.
Atoms C8X, C11Y,
C13X were restrained to be approximately isotropic with the ISOR command.
;

_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^)+(0.0818P)^2^+6.3989P] 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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2688
_refine_ls_number_parameters     236
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1756
_refine_ls_wR_factor_gt          0.1667
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.069
_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 0.49882(3) 0.66246(13) 0.26693(4) 0.0380(3) Uani 1 1 d . . .
O1 O 0.5892(2) 0.7385(7) 0.3500(3) 0.0465(10) Uani 1 1 d . . .
O2 O 0.5945(2) 1.1070(7) 0.3137(3) 0.0426(10) Uani 1 1 d . . .
C1 C 0.6200(3) 0.9309(9) 0.3587(3) 0.0277(11) Uani 1 1 d . . .
C2 C 0.6953(3) 0.9633(8) 0.4281(3) 0.0262(10) Uani 1 1 d . A .
C3 C 0.7628(3) 0.8793(9) 0.4102(4) 0.0321(11) Uani 1 1 d . . .
C4 C 0.8317(3) 0.9285(10) 0.4730(4) 0.0396(13) Uani 1 1 d . B .
H4 H 0.8783 0.8720 0.4622 0.047 Uiso 1 1 calc R . .
C5 C 0.8343(3) 1.0591(9) 0.5516(3) 0.0354(12) Uani 1 1 d . . .
C6 C 0.7664(3) 1.1329(9) 0.5676(3) 0.0350(12) Uani 1 1 d . A .
H6 H 0.7675 1.2177 0.6216 0.042 Uiso 1 1 calc R . .
C7 C 0.6964(3) 1.0881(9) 0.5078(3) 0.0339(12) Uani 1 1 d . . .
C8X C 0.6270(11) 1.208(3) 0.5260(12) 0.036(5) Uani 0.50 1 d PDU A 1
H8X H 0.5903 1.2337 0.4655 0.043 Uiso 0.50 1 calc PR A 1
C9X C 0.6355(10) 1.439(2) 0.5767(12) 0.055(4) Uani 0.50 1 d PD A 1
H9X1 H 0.5874 1.4763 0.5927 0.083 Uiso 0.50 1 calc PR A 1
H9X2 H 0.6477 1.5603 0.5374 0.083 Uiso 0.50 1 calc PR A 1
H9X3 H 0.6770 1.4272 0.6323 0.083 Uiso 0.50 1 calc PR A 1
C10X C 0.5902(11) 1.030(3) 0.5766(14) 0.063(4) Uani 0.50 1 d PD A 1
H10A H 0.5875 0.8804 0.5459 0.094 Uiso 0.50 1 calc PR A 1
H10B H 0.5382 1.0812 0.5769 0.094 Uiso 0.50 1 calc PR A 1
H10C H 0.6211 1.0157 0.6394 0.094 Uiso 0.50 1 calc PR A 1
C8Y C 0.6183(8) 1.133(3) 0.5333(8) 0.028(3) Uani 0.50 1 d PD A 2
H8Y H 0.5758 1.0633 0.4853 0.033 Uiso 0.50 1 calc PR A 2
C9Y C 0.6090(9) 1.393(2) 0.5309(11) 0.048(3) Uani 0.50 1 d PD A 2
H9Y1 H 0.5621 1.4346 0.5493 0.072 Uiso 0.50 1 calc PR A 2
H9Y2 H 0.6054 1.4496 0.4690 0.072 Uiso 0.50 1 calc PR A 2
H9Y3 H 0.6534 1.4643 0.5730 0.072 Uiso 0.50 1 calc PR A 2
C10Y C 0.6146(9) 1.037(3) 0.6260(8) 0.040(3) Uani 0.50 1 d PD A 2
H10D H 0.6531 1.1147 0.6740 0.060 Uiso 0.50 1 calc PR A 2
H10E H 0.6249 0.8707 0.6280 0.060 Uiso 0.50 1 calc PR A 2
H10F H 0.5634 1.0648 0.6356 0.060 Uiso 0.50 1 calc PR A 2
C11X C 0.7619(13) 0.762(3) 0.318(2) 0.028(6) Uani 0.45 1 d PD B 1
H11X H 0.7117 0.8022 0.2751 0.034 Uiso 0.45 1 calc PR B 1
C12X C 0.7610(11) 0.500(2) 0.3329(12) 0.047(4) Uani 0.45 1 d PD B 1
H12A H 0.7580 0.4200 0.2750 0.071 Uiso 0.45 1 calc PR B 1
H12B H 0.7163 0.4584 0.3558 0.071 Uiso 0.45 1 calc PR B 1
H12C H 0.8081 0.4535 0.3773 0.071 Uiso 0.45 1 calc PR B 1
C13X C 0.8241(8) 0.835(3) 0.2721(11) 0.040(4) Uani 0.45 1 d PDU B 1
H13A H 0.8737 0.7740 0.3065 0.060 Uiso 0.45 1 calc PR B 1
H13B H 0.8265 1.0043 0.2706 0.060 Uiso 0.45 1 calc PR B 1
H13C H 0.8124 0.7747 0.2098 0.060 Uiso 0.45 1 calc PR B 1
C11Y C 0.7609(14) 0.724(3) 0.3290(19) 0.035(6) Uani 0.55 1 d PDU B 2
H11Y H 0.7061 0.6829 0.3013 0.042 Uiso 0.55 1 calc PR B 2
C12Y C 0.8057(7) 0.5004(18) 0.3520(8) 0.035(3) Uani 0.55 1 d PD B 2
H12D H 0.8602 0.5357 0.3765 0.052 Uiso 0.55 1 calc PR B 2
H12E H 0.7994 0.4066 0.2967 0.052 Uiso 0.55 1 calc PR B 2
H12F H 0.7865 0.4144 0.3975 0.052 Uiso 0.55 1 calc PR B 2
C13Y C 0.7888(11) 0.870(2) 0.2606(9) 0.063(4) Uani 0.55 1 d PD B 2
H13D H 0.7545 1.0020 0.2424 0.094 Uiso 0.55 1 calc PR B 2
H13E H 0.7893 0.7757 0.2068 0.094 Uiso 0.55 1 calc PR B 2
H13F H 0.8409 0.9250 0.2882 0.094 Uiso 0.55 1 calc PR B 2
C14 C 0.9095(3) 1.1315(10) 0.6169(4) 0.0445(14) Uani 1 1 d . B .
H14 H 0.8952 1.1940 0.6720 0.053 Uiso 1 1 calc R . .
C15 C 0.9450(3) 1.3299(10) 0.5783(4) 0.0456(14) Uani 1 1 d . . .
H15A H 0.9923 1.3777 0.6222 0.068 Uiso 1 1 calc R B .
H15B H 0.9090 1.4598 0.5663 0.068 Uiso 1 1 calc R . .
H15C H 0.9571 1.2819 0.5214 0.068 Uiso 1 1 calc R . .
C16 C 0.9634(4) 0.9427(12) 0.6500(5) 0.065(2) Uani 1 1 d . . .
H16A H 0.9784 0.8705 0.5984 0.098 Uiso 1 1 calc R B .
H16B H 0.9389 0.8273 0.6808 0.098 Uiso 1 1 calc R . .
H16C H 1.0091 1.0040 0.6929 0.098 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 0.0258(4) 0.0466(4) 0.0345(4) -0.0095(3) -0.0061(3) -0.0027(3)
O1 0.034(2) 0.041(2) 0.051(2) -0.0078(19) -0.0148(17) -0.0047(18)
O2 0.0295(19) 0.053(2) 0.037(2) 0.0101(18) -0.0089(16) 0.0010(17)
C1 0.025(2) 0.038(3) 0.020(2) -0.002(2) 0.0065(19) 0.005(2)
C2 0.032(2) 0.022(2) 0.022(2) 0.0017(19) 0.0019(19) 0.0000(19)
C3 0.029(3) 0.029(3) 0.036(3) 0.000(2) 0.002(2) 0.002(2)
C4 0.026(3) 0.038(3) 0.051(3) 0.009(3) 0.003(2) 0.004(2)
C5 0.042(3) 0.028(3) 0.028(3) 0.007(2) -0.007(2) -0.012(2)
C6 0.045(3) 0.035(3) 0.020(2) -0.002(2) -0.002(2) -0.002(2)
C7 0.039(3) 0.034(3) 0.026(3) -0.001(2) 0.004(2) 0.002(2)
C8X 0.036(5) 0.036(5) 0.035(5) -0.0001(10) 0.0087(16) -0.0004(10)
C9X 0.073(11) 0.037(8) 0.058(10) -0.020(8) 0.018(8) -0.010(7)
C10X 0.077(12) 0.046(9) 0.075(12) -0.019(10) 0.038(12) -0.013(8)
C8Y 0.034(7) 0.036(8) 0.015(6) -0.008(6) 0.009(5) -0.005(7)
C9Y 0.061(10) 0.036(9) 0.057(10) 0.012(7) 0.032(8) 0.014(7)
C10Y 0.058(9) 0.043(8) 0.025(6) -0.001(6) 0.021(6) -0.004(6)
C11X 0.026(8) 0.016(9) 0.044(13) 0.003(7) 0.012(6) 0.010(6)
C12X 0.069(11) 0.027(8) 0.053(10) 0.007(7) 0.029(9) 0.013(8)
C13X 0.039(4) 0.040(4) 0.040(4) 0.0003(10) 0.0100(14) 0.0003(10)
C11Y 0.035(6) 0.035(6) 0.035(6) -0.0002(10) 0.0085(18) 0.0000(10)
C12Y 0.049(7) 0.023(5) 0.030(5) -0.002(4) 0.008(5) 0.006(6)
C13Y 0.099(14) 0.055(9) 0.032(7) 0.009(6) 0.010(8) 0.011(9)
C14 0.040(3) 0.048(4) 0.038(3) 0.003(3) -0.007(2) -0.009(3)
C15 0.041(3) 0.043(3) 0.047(3) -0.004(3) 0.000(3) -0.017(3)
C16 0.053(4) 0.046(4) 0.074(5) 0.008(3) -0.026(3) -0.007(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
Cu1 O2 1.844(3) 2_645 yes
Cu1 O1 1.846(3) . yes
O1 C1 1.236(6) . ?
O2 C1 1.248(6) . ?
O2 Cu1 1.844(3) 2_655 yes
C1 C2 1.506(6) . ?
C2 C3 1.394(7) . ?
C2 C7 1.403(7) . ?
C3 C4 1.393(7) . ?
C3 C11Y 1.51(3) . ?
C3 C11X 1.55(3) . ?
C4 C5 1.401(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.369(8) . ?
C5 C14 1.524(7) . ?
C6 C7 1.382(7) . ?
C6 H6 0.9500 . ?
C7 C8X 1.510(19) . ?
C7 C8Y 1.567(14) . ?
C8X C10X 1.525(16) . ?
C8X C9X 1.529(17) . ?
C8X H8X 1.0000 . ?
C9X H9X1 0.9800 . ?
C9X H9X2 0.9800 . ?
C9X H9X3 0.9800 . ?
C10X H10A 0.9800 . ?
C10X H10B 0.9800 . ?
C10X H10C 0.9800 . ?
C8Y C9Y 1.515(16) . ?
C8Y C10Y 1.527(15) . ?
C8Y H8Y 1.0000 . ?
C9Y H9Y1 0.9800 . ?
C9Y H9Y2 0.9800 . ?
C9Y H9Y3 0.9800 . ?
C10Y H10D 0.9800 . ?
C10Y H10E 0.9800 . ?
C10Y H10F 0.9800 . ?
C11X C13X 1.515(17) . ?
C11X C12X 1.532(17) . ?
C11X H11X 1.0000 . ?
C12X H12A 0.9800 . ?
C12X H12B 0.9800 . ?
C12X H12C 0.9800 . ?
C13X H13A 0.9800 . ?
C13X H13B 0.9800 . ?
C13X H13C 0.9800 . ?
C11Y C13Y 1.514(16) . ?
C11Y C12Y 1.520(17) . ?
C11Y H11Y 1.0000 . ?
C12Y H12D 0.9800 . ?
C12Y H12E 0.9800 . ?
C12Y H12F 0.9800 . ?
C13Y H13D 0.9800 . ?
C13Y H13E 0.9800 . ?
C13Y H13F 0.9800 . ?
C14 C16 1.464(9) . ?
C14 C15 1.500(8) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O2 Cu1 O1 175.67(18) 2_645 . yes
O2 Cu1 Cu1 76.31(13) 2_645 2_645 yes
O1 Cu1 Cu1 107.76(14) . 2_645 yes
O2 Cu1 Cu1 96.07(13) 2_645 2_655 yes
O1 Cu1 Cu1 80.57(14) . 2_655 yes
Cu1 Cu1 Cu1 159.43(5) 2_645 2_655 yes
C1 O1 Cu1 125.7(4) . . ?
C1 O2 Cu1 130.9(4) . 2_655 ?
O1 C1 O2 125.6(4) . . ?
O1 C1 C2 119.2(4) . . ?
O2 C1 C2 115.1(4) . . ?
C3 C2 C7 121.3(4) . . ?
C3 C2 C1 119.7(4) . . ?
C7 C2 C1 118.9(4) . . ?
C4 C3 C2 117.8(5) . . ?
C4 C3 C11Y 120.9(10) . . ?
C2 C3 C11Y 121.2(10) . . ?
C4 C3 C11X 121.0(10) . . ?
C2 C3 C11X 120.8(9) . . ?
C3 C4 C5 121.9(5) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.3(5) . . ?
C6 C5 C14 119.1(5) . . ?
C4 C5 C14 122.5(5) . . ?
C5 C6 C7 122.2(5) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C2 118.5(5) . . ?
C6 C7 C8X 117.0(8) . . ?
C2 C7 C8X 123.8(8) . . ?
C6 C7 C8Y 122.3(6) . . ?
C2 C7 C8Y 118.3(6) . . ?
C7 C8X C10X 105.3(13) . . ?
C7 C8X C9X 120.5(13) . . ?
C10X C8X C9X 109.7(13) . . ?
C7 C8X H8X 106.9 . . ?
C10X C8X H8X 106.9 . . ?
C9X C8X H8X 106.9 . . ?
C9Y C8Y C10Y 110.6(10) . . ?
C9Y C8Y C7 105.1(12) . . ?
C10Y C8Y C7 114.3(11) . . ?
C9Y C8Y H8Y 108.9 . . ?
C10Y C8Y H8Y 108.9 . . ?
C7 C8Y H8Y 108.9 . . ?
C8Y C9Y H9Y1 109.5 . . ?
C8Y C9Y H9Y2 109.5 . . ?
H9Y1 C9Y H9Y2 109.5 . . ?
C8Y C9Y H9Y3 109.5 . . ?
H9Y1 C9Y H9Y3 109.5 . . ?
H9Y2 C9Y H9Y3 109.5 . . ?
C8Y C10Y H10D 109.5 . . ?
C8Y C10Y H10E 109.5 . . ?
H10D C10Y H10E 109.5 . . ?
C8Y C10Y H10F 109.5 . . ?
H10D C10Y H10F 109.5 . . ?
H10E C10Y H10F 109.5 . . ?
C13X C11X C12X 112.4(13) . . ?
C13X C11X C3 116.3(18) . . ?
C12X C11X C3 107.4(16) . . ?
C13X C11X H11X 106.7 . . ?
C12X C11X H11X 106.7 . . ?
C3 C11X H11X 106.7 . . ?
C13Y C11Y C3 106.4(15) . . ?
C13Y C11Y C12Y 112.5(13) . . ?
C3 C11Y C12Y 114.5(18) . . ?
C13Y C11Y H11Y 107.7 . . ?
C3 C11Y H11Y 107.7 . . ?
C12Y C11Y H11Y 107.7 . . ?
C11Y C12Y H12D 109.5 . . ?
C11Y C12Y H12E 109.5 . . ?
H12D C12Y H12E 109.5 . . ?
C11Y C12Y H12F 109.5 . . ?
H12D C12Y H12F 109.5 . . ?
H12E C12Y H12F 109.5 . . ?
C11Y C13Y H13D 109.5 . . ?
C11Y C13Y H13E 109.5 . . ?
H13D C13Y H13E 109.5 . . ?
C11Y C13Y H13F 109.5 . . ?
H13D C13Y H13F 109.5 . . ?
H13E C13Y H13F 109.5 . . ?
C16 C14 C15 113.3(6) . . ?
C16 C14 C5 115.1(5) . . ?
C15 C14 C5 110.7(5) . . ?
C16 C14 H14 105.7 . . ?
C15 C14 H14 105.7 . . ?
C5 C14 H14 105.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.341
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.102
#==END


data_2
_database_code_depnum_ccdc_archive 'CCDC 814792'
#TrackingRef '- combined.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2,4,6-triisopropylbenzoato-O,O'-copper(I)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H23 Cu O2'
_chemical_formula_sum            'C16 H23 Cu O2'
_chemical_formula_weight         310.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c n '
_symmetry_space_group_name_Hall  '-P 2n 2ab '
_symmetry_int_tables_number      60

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

_cell_length_a                   34.687(3)
_cell_length_b                   10.2092(8)
_cell_length_c                   8.5888(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3041.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7115
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    1.432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (Bruker-AXS, 2003)
;
_exptl_absorpt_correction_T_min  0.6342
_exptl_absorpt_correction_T_max  0.9190

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.30\% \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24294
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         28.28
_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_reflns_number_total             3638
_reflns_number_gt                3228
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_cell_refinement       'SAINT Ver. 6.22 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'

_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.
;

_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^)+(0.0497P)^2^+2.0519P] 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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3638
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_diff_density_max         1.247
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.071
_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 0.5000 0.68863(3) 1.2500 0.01862(11) Uani 1 2 d S . .
Cu2 Cu 0.5000 0.5000 1.0000 0.02110(11) Uani 1 2 d S . .
O1 O 0.45285(3) 0.71684(13) 1.15773(15) 0.0225(3) Uani 1 1 d . . .
O2 O 0.45431(4) 0.58472(12) 0.94969(15) 0.0234(3) Uani 1 1 d . . .
C1 C 0.43950(5) 0.67412(16) 1.0311(2) 0.0168(3) Uani 1 1 d . . .
C2 C 0.40299(5) 0.73582(16) 0.9716(2) 0.0164(3) Uani 1 1 d . . .
C3 C 0.36854(5) 0.72283(17) 1.0565(2) 0.0174(3) Uani 1 1 d . . .
C4 C 0.33503(5) 0.77600(17) 0.9927(2) 0.0195(4) Uani 1 1 d . . .
H4 H 0.3114 0.7664 1.0478 0.023 Uiso 1 1 calc R . .
C5 C 0.33490(5) 0.84263(17) 0.8514(2) 0.0176(3) Uani 1 1 d . . .
C6 C 0.36974(5) 0.85881(17) 0.77353(19) 0.0176(3) Uani 1 1 d . . .
H6 H 0.3702 0.9070 0.6789 0.021 Uiso 1 1 calc R . .
C7 C 0.40412(5) 0.80593(16) 0.8310(2) 0.0163(3) Uani 1 1 d . . .
C8 C 0.36640(5) 0.65258(19) 1.2132(2) 0.0205(4) Uani 1 1 d . . .
H8 H 0.3933 0.6328 1.2476 0.025 Uiso 1 1 calc R . .
C9 C 0.34780(7) 0.7406(2) 1.3355(2) 0.0338(5) Uani 1 1 d . . .
H9A H 0.3612 0.8251 1.3381 0.051 Uiso 1 1 calc R . .
H9B H 0.3496 0.6987 1.4378 0.051 Uiso 1 1 calc R . .
H9C H 0.3206 0.7547 1.3090 0.051 Uiso 1 1 calc R . .
C10 C 0.34464(8) 0.5232(2) 1.1988(3) 0.0379(5) Uani 1 1 d . . .
H10A H 0.3434 0.4806 1.3010 0.057 Uiso 1 1 calc R . .
H10B H 0.3581 0.4659 1.1251 0.057 Uiso 1 1 calc R . .
H10C H 0.3184 0.5401 1.1613 0.057 Uiso 1 1 calc R . .
C11 C 0.29791(5) 0.89312(18) 0.7777(2) 0.0191(4) Uani 1 1 d . . .
H11 H 0.3053 0.9559 0.6934 0.023 Uiso 1 1 calc R . .
C12 C 0.27176(5) 0.9660(2) 0.8912(2) 0.0269(4) Uani 1 1 d . . .
H12A H 0.2645 0.9073 0.9767 0.040 Uiso 1 1 calc R . .
H12B H 0.2485 0.9952 0.8367 0.040 Uiso 1 1 calc R . .
H12C H 0.2855 1.0421 0.9331 0.040 Uiso 1 1 calc R . .
C13 C 0.27595(6) 0.7800(2) 0.7017(3) 0.0277(4) Uani 1 1 d . . .
H13A H 0.2929 0.7345 0.6282 0.041 Uiso 1 1 calc R . .
H13B H 0.2535 0.8145 0.6459 0.041 Uiso 1 1 calc R . .
H13C H 0.2674 0.7186 0.7822 0.041 Uiso 1 1 calc R . .
C14 C 0.44134(5) 0.82782(18) 0.7405(2) 0.0209(4) Uani 1 1 d . . .
H14 H 0.4633 0.8013 0.8090 0.025 Uiso 1 1 calc R . .
C15 C 0.44244(7) 0.7418(2) 0.5960(3) 0.0404(5) Uani 1 1 d . . .
H15A H 0.4388 0.6500 0.6261 0.061 Uiso 1 1 calc R . .
H15B H 0.4674 0.7518 0.5441 0.061 Uiso 1 1 calc R . .
H15C H 0.4218 0.7682 0.5246 0.061 Uiso 1 1 calc R . .
C16 C 0.44701(6) 0.9715(2) 0.6972(3) 0.0321(5) Uani 1 1 d . . .
H16A H 0.4722 0.9826 0.6471 0.048 Uiso 1 1 calc R . .
H16B H 0.4459 1.0254 0.7916 0.048 Uiso 1 1 calc R . .
H16C H 0.4266 0.9988 0.6253 0.048 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 0.01416(17) 0.02243(18) 0.01927(18) 0.000 -0.00441(11) 0.000
Cu2 0.01674(18) 0.01881(18) 0.0278(2) -0.00225(12) -0.00374(12) 0.00672(10)
O1 0.0183(6) 0.0264(7) 0.0228(6) -0.0032(5) -0.0062(5) 0.0043(5)
O2 0.0197(6) 0.0228(6) 0.0277(7) -0.0036(5) -0.0049(5) 0.0078(5)
C1 0.0149(8) 0.0152(8) 0.0203(8) 0.0044(6) -0.0012(6) -0.0006(6)
C2 0.0142(8) 0.0156(8) 0.0192(8) -0.0009(6) -0.0032(6) 0.0014(6)
C3 0.0161(8) 0.0180(8) 0.0182(8) 0.0013(6) -0.0021(6) 0.0015(6)
C4 0.0140(8) 0.0217(9) 0.0229(9) 0.0023(7) 0.0010(6) 0.0016(6)
C5 0.0149(8) 0.0171(8) 0.0209(8) 0.0005(6) -0.0026(6) 0.0012(6)
C6 0.0187(8) 0.0173(8) 0.0167(8) 0.0022(6) -0.0013(6) 0.0021(6)
C7 0.0157(8) 0.0152(8) 0.0180(8) -0.0007(6) 0.0003(6) 0.0008(6)
C8 0.0172(8) 0.0242(9) 0.0202(8) 0.0055(7) -0.0001(7) 0.0038(7)
C9 0.0475(13) 0.0348(11) 0.0192(9) 0.0019(8) 0.0015(9) 0.0093(9)
C10 0.0571(15) 0.0273(10) 0.0294(11) 0.0098(9) -0.0071(10) -0.0085(10)
C11 0.0146(8) 0.0209(9) 0.0217(8) 0.0041(7) -0.0039(6) 0.0015(6)
C12 0.0226(9) 0.0295(10) 0.0285(10) 0.0003(8) -0.0046(8) 0.0100(8)
C13 0.0215(9) 0.0248(9) 0.0367(11) -0.0013(8) -0.0077(8) 0.0002(7)
C14 0.0154(8) 0.0239(9) 0.0232(9) 0.0040(7) 0.0015(6) 0.0022(7)
C15 0.0339(12) 0.0484(14) 0.0388(12) -0.0145(10) 0.0168(10) -0.0020(10)
C16 0.0243(10) 0.0297(10) 0.0423(12) 0.0097(9) 0.0066(9) -0.0010(8)

_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 1.8401(12) 3_657 yes
Cu1 O1 1.8401(12) . yes
Cu1 Cu2 2.8843(3) . yes
Cu1 Cu2 2.8843(3) 3_657 yes
Cu2 O2 1.8565(12) 5_667 yes
Cu2 O2 1.8565(12) . yes
Cu2 Cu1 2.8843(3) 5_667 yes
O1 C1 1.260(2) . yes
O2 C1 1.259(2) . yes
C1 C2 1.504(2) . ?
C2 C7 1.404(2) . ?
C2 C3 1.406(2) . ?
C3 C4 1.395(2) . ?
C3 C8 1.527(2) . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(2) . ?
C5 C11 1.521(2) . ?
C6 C7 1.399(2) . ?
C6 H6 0.9500 . ?
C7 C14 1.523(2) . ?
C8 C9 1.526(3) . ?
C8 C10 1.526(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.525(3) . ?
C11 C13 1.529(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.521(3) . ?
C14 C16 1.526(3) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O1 Cu1 O1 161.99(8) 3_657 . yes
O1 Cu1 Cu2 115.16(4) 3_657 . yes
O1 Cu1 Cu2 77.52(4) . . yes
O1 Cu1 Cu2 77.52(4) 3_657 3_657 yes
O1 Cu1 Cu2 115.16(4) . 3_657 yes
Cu2 Cu1 Cu2 96.224(11) . 3_657 yes
O2 Cu2 O2 180.00(4) 5_667 . yes
O2 Cu2 Cu1 97.92(4) 5_667 . yes
O2 Cu2 Cu1 82.08(4) . . yes
O2 Cu2 Cu1 82.08(4) 5_667 5_667 yes
O2 Cu2 Cu1 97.92(4) . 5_667 yes
Cu1 Cu2 Cu1 180.0 . 5_667 yes
C1 O1 Cu1 130.11(12) . . yes
C1 O2 Cu2 123.82(12) . . yes
O2 C1 O1 125.48(16) . . ?
O2 C1 C2 117.26(15) . . ?
O1 C1 C2 117.26(15) . . ?
C7 C2 C3 121.19(15) . . ?
C7 C2 C1 118.84(15) . . ?
C3 C2 C1 119.96(15) . . ?
C4 C3 C2 117.88(15) . . ?
C4 C3 C8 119.23(15) . . ?
C2 C3 C8 122.89(15) . . ?
C5 C4 C3 122.38(16) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 118.34(15) . . ?
C4 C5 C11 122.13(15) . . ?
C6 C5 C11 119.49(15) . . ?
C5 C6 C7 121.68(16) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C2 118.43(15) . . ?
C6 C7 C14 119.08(15) . . ?
C2 C7 C14 122.49(15) . . ?
C9 C8 C10 110.88(17) . . ?
C9 C8 C3 110.52(15) . . ?
C10 C8 C3 111.08(16) . . ?
C9 C8 H8 108.1 . . ?
C10 C8 H8 108.1 . . ?
C3 C8 H8 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 C12 113.62(15) . . ?
C5 C11 C13 110.00(15) . . ?
C12 C11 C13 110.17(16) . . ?
C5 C11 H11 107.6 . . ?
C12 C11 H11 107.6 . . ?
C13 C11 H11 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C7 110.66(16) . . ?
C15 C14 C16 110.69(17) . . ?
C7 C14 C16 112.00(15) . . ?
C15 C14 H14 107.8 . . ?
C7 C14 H14 107.8 . . ?
C16 C14 H14 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

data_3
_database_code_depnum_ccdc_archive 'CCDC 814793'
#TrackingRef '- combined.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bis-(2,4,6-triisopropylbenzoato-O,O')-dicopper(I,I)
bis(dichlorobenzene)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H54 Cl4 Cu2 O4'
_chemical_formula_sum            'C44 H54 Cl4 Cu2 O4'
_chemical_formula_weight         915.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc '
_symmetry_int_tables_number      14

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

_cell_length_a                   8.4789(9)
_cell_length_b                   11.4630(13)
_cell_length_c                   22.026(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.125(2)
_cell_angle_gamma                90.00
_cell_volume                     2139.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5702
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    1.285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (Bruker-AXS, 2003)
;
_exptl_absorpt_correction_T_min  0.7149
_exptl_absorpt_correction_T_max  0.8017

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.30\% \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18036
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         28.28
_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total             4987
_reflns_number_gt                4341
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_cell_refinement       'SAINT Ver. 6.22 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'

_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.
;

_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^)+(0.0504P)^2^+0.8407P] 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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4987
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.076
_refine_ls_shift/su_max          0.002
_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 1.01633(3) 0.593209(17) 1.028713(9) 0.02062(8) Uani 1 1 d . . .
O1 O 0.88909(15) 0.65625(10) 0.96580(5) 0.0218(3) Uani 1 1 d . . .
O2 O 1.15109(15) 0.51292(11) 1.08375(6) 0.0214(3) Uani 1 1 d . . .
C1 C 0.82990(19) 0.59547(14) 0.92291(8) 0.0169(3) Uani 1 1 d . . .
C2 C 0.73067(19) 0.66190(14) 0.87687(7) 0.0159(3) Uani 1 1 d . . .
C3 C 0.80096(19) 0.70259(14) 0.82432(7) 0.0167(3) Uani 1 1 d . . .
C4 C 0.7140(2) 0.77602(14) 0.78594(8) 0.0179(3) Uani 1 1 d . . .
H4 H 0.7603 0.8044 0.7502 0.022 Uiso 1 1 calc R . .
C5 C 0.5601(2) 0.80948(14) 0.79844(8) 0.0174(3) Uani 1 1 d . . .
C6 C 0.4924(2) 0.76411(14) 0.84969(8) 0.0177(3) Uani 1 1 d . . .
H6 H 0.3868 0.7846 0.8580 0.021 Uiso 1 1 calc R . .
C7 C 0.5749(2) 0.68926(14) 0.88943(7) 0.0176(3) Uani 1 1 d . . .
C8 C 0.9647(2) 0.66018(15) 0.80865(8) 0.0186(3) Uani 1 1 d . . .
H8 H 1.0205 0.6357 0.8474 0.022 Uiso 1 1 calc R . .
C9 C 0.9491(2) 0.55293(17) 0.76798(9) 0.0272(4) Uani 1 1 d . . .
H9A H 0.8924 0.4915 0.7891 0.041 Uiso 1 1 calc R . .
H9B H 1.0544 0.5248 0.7583 0.041 Uiso 1 1 calc R . .
H9C H 0.8905 0.5735 0.7303 0.041 Uiso 1 1 calc R . .
C10 C 1.0659(2) 0.75343(16) 0.77915(9) 0.0238(4) Uani 1 1 d . . .
H10A H 1.1728 0.7232 0.7744 0.036 Uiso 1 1 calc R . .
H10B H 1.0705 0.8231 0.8050 0.036 Uiso 1 1 calc R . .
H10C H 1.0191 0.7738 0.7392 0.036 Uiso 1 1 calc R . .
C11 C 0.4683(2) 0.89238(14) 0.75654(8) 0.0194(3) Uani 1 1 d . . .
H11 H 0.3617 0.9033 0.7736 0.023 Uiso 1 1 calc R . .
C12 C 0.4437(2) 0.84233(17) 0.69262(9) 0.0278(4) Uani 1 1 d . . .
H12A H 0.5464 0.8297 0.6747 0.042 Uiso 1 1 calc R . .
H12B H 0.3816 0.8972 0.6674 0.042 Uiso 1 1 calc R . .
H12C H 0.3873 0.7679 0.6947 0.042 Uiso 1 1 calc R . .
C13 C 0.5466(3) 1.01139(17) 0.75471(10) 0.0327(5) Uani 1 1 d . . .
H13A H 0.5603 1.0419 0.7961 0.049 Uiso 1 1 calc R . .
H13B H 0.4800 1.0649 0.7303 0.049 Uiso 1 1 calc R . .
H13C H 0.6499 1.0042 0.7365 0.049 Uiso 1 1 calc R . .
C14 C 0.4957(2) 0.63750(16) 0.94418(8) 0.0215(4) Uani 1 1 d . . .
H14 H 0.5657 0.5741 0.9609 0.026 Uiso 1 1 calc R . .
C15 C 0.3371(3) 0.5824(2) 0.92588(11) 0.0393(5) Uani 1 1 d . . .
H15A H 0.2961 0.5400 0.9606 0.059 Uiso 1 1 calc R . .
H15B H 0.3510 0.5282 0.8921 0.059 Uiso 1 1 calc R . .
H15C H 0.2623 0.6437 0.9132 0.059 Uiso 1 1 calc R . .
C16 C 0.4767(3) 0.7270(2) 0.99429(10) 0.0410(5) Uani 1 1 d . . .
H16A H 0.5804 0.7588 1.0066 0.061 Uiso 1 1 calc R . .
H16B H 0.4296 0.6897 1.0293 0.061 Uiso 1 1 calc R . .
H16C H 0.4080 0.7903 0.9793 0.061 Uiso 1 1 calc R . .
Cl1 Cl 0.85373(6) 0.73628(4) 1.11481(2) 0.03112(12) Uani 1 1 d . . .
Cl2 Cl 0.71259(7) 0.98631(5) 1.08941(3) 0.04503(15) Uani 1 1 d . . .
C17 C 0.9760(2) 0.85268(17) 1.09909(8) 0.0250(4) Uani 1 1 d . . .
C18 C 1.1369(2) 0.83437(19) 1.09827(9) 0.0322(4) Uani 1 1 d . . .
H18 H 1.1795 0.7589 1.1059 0.039 Uiso 1 1 calc R . .
C19 C 1.2359(3) 0.9273(2) 1.08616(11) 0.0434(6) Uani 1 1 d . . .
H19 H 1.3467 0.9156 1.0855 0.052 Uiso 1 1 calc R . .
C20 C 1.1735(3) 1.0366(2) 1.07513(11) 0.0465(6) Uani 1 1 d . . .
H20 H 1.2419 1.0999 1.0671 0.056 Uiso 1 1 calc R . .
C21 C 1.0124(3) 1.0550(2) 1.07568(10) 0.0391(5) Uani 1 1 d . . .
H21 H 0.9700 1.1304 1.0677 0.047 Uiso 1 1 calc R . .
C22 C 0.9138(2) 0.96286(17) 1.08784(9) 0.0290(4) Uani 1 1 d . . .

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 0.02763(14) 0.01368(12) 0.02004(13) -0.00016(8) -0.00586(9) 0.00321(8)
O1 0.0289(7) 0.0160(6) 0.0199(6) -0.0003(5) -0.0065(5) 0.0037(5)
O2 0.0278(7) 0.0145(6) 0.0213(6) 0.0003(5) -0.0045(5) 0.0027(5)
C1 0.0161(8) 0.0177(8) 0.0173(8) 0.0026(6) 0.0036(6) 0.0010(6)
C2 0.0191(8) 0.0119(7) 0.0166(8) -0.0007(6) 0.0001(6) 0.0000(6)
C3 0.0184(8) 0.0133(7) 0.0185(8) -0.0016(6) 0.0003(6) -0.0002(6)
C4 0.0203(8) 0.0161(8) 0.0176(8) 0.0009(6) 0.0020(6) -0.0008(6)
C5 0.0205(8) 0.0117(7) 0.0198(8) 0.0006(6) -0.0024(6) -0.0001(6)
C6 0.0172(8) 0.0154(8) 0.0205(8) -0.0007(6) 0.0010(6) 0.0011(6)
C7 0.0212(8) 0.0144(8) 0.0173(8) -0.0002(6) 0.0012(6) 0.0007(6)
C8 0.0179(8) 0.0180(8) 0.0199(8) 0.0024(7) 0.0016(6) 0.0018(6)
C9 0.0246(9) 0.0213(9) 0.0362(11) -0.0046(8) 0.0087(8) 0.0021(7)
C10 0.0195(9) 0.0230(9) 0.0291(10) 0.0019(7) 0.0030(7) -0.0018(7)
C11 0.0201(8) 0.0164(8) 0.0217(9) 0.0041(6) -0.0001(7) 0.0026(6)
C12 0.0320(10) 0.0259(10) 0.0248(9) 0.0023(8) -0.0059(8) 0.0066(8)
C13 0.0380(11) 0.0183(9) 0.0411(12) 0.0082(8) -0.0095(9) -0.0015(8)
C14 0.0221(9) 0.0231(9) 0.0194(8) 0.0050(7) 0.0025(7) 0.0038(7)
C15 0.0322(11) 0.0532(15) 0.0329(11) 0.0139(10) 0.0038(9) -0.0147(10)
C16 0.0605(15) 0.0405(13) 0.0228(10) -0.0004(9) 0.0138(10) 0.0026(11)
Cl1 0.0397(3) 0.0267(2) 0.0272(2) -0.00221(18) 0.00559(19) -0.00333(19)
Cl2 0.0422(3) 0.0418(3) 0.0513(4) -0.0064(3) 0.0040(3) 0.0188(2)
C17 0.0324(10) 0.0241(9) 0.0186(8) -0.0041(7) 0.0029(7) -0.0001(7)
C18 0.0323(11) 0.0336(11) 0.0303(10) -0.0108(9) -0.0026(8) 0.0038(8)
C19 0.0344(12) 0.0559(15) 0.0401(13) -0.0225(11) 0.0052(10) -0.0115(10)
C20 0.0613(16) 0.0426(14) 0.0367(12) -0.0157(10) 0.0149(11) -0.0251(12)
C21 0.0644(16) 0.0237(10) 0.0294(11) -0.0051(9) 0.0052(10) -0.0018(10)
C22 0.0367(11) 0.0268(10) 0.0238(9) -0.0045(8) 0.0055(8) 0.0041(8)

_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 1.8697(12) . yes
Cu1 O2 1.8760(12) . yes
Cu1 Cu1 2.4934(5) 3_767 yes
O1 C1 1.263(2) . yes
O2 C1 1.262(2) 3_767 yes
C1 O2 1.262(2) 3_767 yes
C1 C2 1.501(2) . ?
C2 C7 1.395(2) . ?
C2 C3 1.401(2) . ?
C3 C4 1.386(2) . ?
C3 C8 1.523(2) . ?
C4 C5 1.398(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 C11 1.519(2) . ?
C6 C7 1.395(2) . ?
C6 H6 0.9500 . ?
C7 C14 1.522(2) . ?
C8 C9 1.524(3) . ?
C8 C10 1.530(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.518(3) . ?
C11 C12 1.528(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C16 1.520(3) . ?
C14 C15 1.526(3) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
Cl1 C17 1.733(2) . yes
Cl2 C22 1.729(2) . yes
C17 C18 1.381(3) . ?
C17 C22 1.388(3) . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(3) . ?
C21 H21 0.9500 . ?

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 O2 171.67(5) . . yes
O1 Cu1 Cu1 84.55(4) . 3_767 yes
O2 Cu1 Cu1 87.76(4) . 3_767 yes
C1 O1 Cu1 122.93(11) . . yes
C1 O2 Cu1 119.02(11) 3_767 . yes
O2 C1 O1 125.54(16) 3_767 . ?
O2 C1 C2 119.44(15) 3_767 . ?
O1 C1 C2 115.02(14) . . ?
C7 C2 C3 121.59(15) . . ?
C7 C2 C1 119.41(14) . . ?
C3 C2 C1 118.82(14) . . ?
C4 C3 C2 118.24(15) . . ?
C4 C3 C8 121.63(15) . . ?
C2 C3 C8 120.02(14) . . ?
C3 C4 C5 121.74(15) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.37(15) . . ?
C6 C5 C11 120.76(15) . . ?
C4 C5 C11 120.87(15) . . ?
C5 C6 C7 121.91(15) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C2 C7 C6 118.05(15) . . ?
C2 C7 C14 121.22(15) . . ?
C6 C7 C14 120.72(15) . . ?
C3 C8 C9 109.32(14) . . ?
C3 C8 C10 113.79(14) . . ?
C9 C8 C10 110.58(15) . . ?
C3 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
C10 C8 H8 107.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C5 111.35(15) . . ?
C13 C11 C12 110.98(16) . . ?
C5 C11 C12 111.99(14) . . ?
C13 C11 H11 107.4 . . ?
C5 C11 H11 107.4 . . ?
C12 C11 H11 107.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C14 C7 111.94(16) . . ?
C16 C14 C15 110.81(18) . . ?
C7 C14 C15 111.25(15) . . ?
C16 C14 H14 107.5 . . ?
C7 C14 H14 107.5 . . ?
C15 C14 H14 107.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 120.35(19) . . ?
C18 C17 Cl1 118.97(16) . . ?
C22 C17 Cl1 120.68(15) . . ?
C17 C18 C19 119.3(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.7(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 119.4(2) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C17 120.1(2) . . ?
C21 C22 Cl2 119.39(17) . . ?
C17 C22 Cl2 120.46(16) . . ?

data_4
_database_code_depnum_ccdc_archive 'CCDC 814794'
#TrackingRef '- combined.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(2,4,6-triisopropyl)benzoic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 O2'
_chemical_formula_sum            'C16 H24 O2'
_chemical_formula_weight         248.35

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'
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 '
_symmetry_int_tables_number      2

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

_cell_length_a                   7.847(3)
_cell_length_b                   9.339(3)
_cell_length_c                   11.335(4)
_cell_angle_alpha                94.552(6)
_cell_angle_beta                 99.047(6)
_cell_angle_gamma                112.924(5)
_cell_volume                     746.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3927
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.21

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (Bruker-AXS, 2003)
;
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_T_max  0.9958

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.30\% \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6540
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         28.22
_reflns_number_total             3360
_reflns_number_gt                2772
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_cell_refinement       'SAINT Ver. 6.22 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'

_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.
;

_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^)+(0.0735P)^2^+0.1932P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3360
_refine_ls_number_parameters     258
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.061
_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
O1 O 0.18984(14) 0.66785(12) -0.01044(8) 0.0294(3) Uani 1 1 d . . .
O2 O 0.10311(14) 0.56521(12) 0.15313(9) 0.0313(3) Uani 1 1 d D . .
H2O H 0.009(2) 0.492(2) 0.1012(15) 0.038 Uiso 1 1 d D . .
C1 C 0.38239(17) 0.79952(14) 0.18282(11) 0.0190(3) Uani 1 1 d . . .
C2 C 0.54598(18) 1.07214(14) 0.27054(11) 0.0207(3) Uani 1 1 d . . .
C3 C 0.21421(17) 0.66930(14) 0.10237(11) 0.0194(3) Uani 1 1 d . . .
C4 C 0.68263(18) 0.89068(15) 0.31918(12) 0.0220(3) Uani 1 1 d . . .
C5 C 0.38921(17) 0.95285(14) 0.19466(11) 0.0191(3) Uani 1 1 d . . .
C6 C 0.52852(18) 0.76640(14) 0.24476(11) 0.0206(3) Uani 1 1 d . . .
C7 C 0.69342(17) 1.04335(14) 0.33383(11) 0.0205(3) Uani 1 1 d . . .
C8 C 0.85716(19) 1.17372(15) 0.42183(12) 0.0239(3) Uani 1 1 d . . .
C9 C 0.9478(2) 1.32173(16) 0.36622(14) 0.0279(3) Uani 1 1 d . . .
C10 C 0.23169(18) 0.99136(15) 0.12869(12) 0.0230(3) Uani 1 1 d . . .
C11 C 0.5257(2) 0.60171(15) 0.23207(13) 0.0259(3) Uani 1 1 d . . .
C12 C 0.5300(3) 0.54369(19) 0.35360(16) 0.0378(4) Uani 1 1 d . . .
C13 C 0.7901(3) 1.2123(2) 0.53511(14) 0.0398(4) Uani 1 1 d . . .
C14 C 0.6896(3) 0.5968(2) 0.17661(17) 0.0404(4) Uani 1 1 d . . .
C15 C 0.1616(3) 1.0802(2) 0.21457(18) 0.0451(5) Uani 1 1 d . . .
C16 C 0.2965(2) 1.0832(2) 0.02712(17) 0.0423(4) Uani 1 1 d . . .
H1 H 0.551(2) 1.181(2) 0.2781(14) 0.029(4) Uiso 1 1 d . . .
H2 H 0.787(2) 0.8695(19) 0.3634(14) 0.025(4) Uiso 1 1 d . . .
H3 H 0.953(2) 1.133(2) 0.4453(15) 0.029(4) Uiso 1 1 d . . .
H4 H 0.121(2) 0.8916(19) 0.0940(14) 0.024(4) Uiso 1 1 d . . .
H5 H 0.860(2) 1.374(2) 0.3444(15) 0.033(4) Uiso 1 1 d . . .
H6 H 0.985(3) 1.301(2) 0.2898(18) 0.041(5) Uiso 1 1 d . . .
H7 H 0.408(2) 0.527(2) 0.1761(15) 0.032(4) Uiso 1 1 d . . .
H8 H 1.061(2) 1.3974(19) 0.4248(15) 0.026(4) Uiso 1 1 d . . .
H9 H 0.649(3) 0.613(2) 0.4143(17) 0.044(5) Uiso 1 1 d . . .
H10 H 0.052(3) 1.093(2) 0.1718(17) 0.043(5) Uiso 1 1 d . . .
H11 H 0.895(3) 1.292(2) 0.5948(17) 0.045(5) Uiso 1 1 d . . .
H12 H 0.405(3) 1.180(3) 0.0590(18) 0.047(5) Uiso 1 1 d . . .
H13 H 0.687(3) 0.632(3) 0.097(2) 0.059(6) Uiso 1 1 d . . .
H14 H 0.198(3) 1.111(2) -0.0138(18) 0.047(5) Uiso 1 1 d . . .
H15 H 0.683(3) 0.487(2) 0.1657(17) 0.047(5) Uiso 1 1 d . . .
H16 H 0.420(3) 0.541(3) 0.387(2) 0.067(7) Uiso 1 1 d . . .
H17 H 0.822(3) 0.672(2) 0.2324(18) 0.047(5) Uiso 1 1 d . . .
H18 H 0.333(3) 1.021(3) -0.034(2) 0.072(7) Uiso 1 1 d . . .
H19 H 0.266(3) 1.190(3) 0.2536(19) 0.057(6) Uiso 1 1 d . . .
H20 H 0.732(3) 1.119(3) 0.5716(19) 0.056(6) Uiso 1 1 d . . .
H1A H 0.524(2) 0.435(2) 0.3452(16) 0.039(5) Uiso 1 1 d . . .
H2A H 0.693(3) 1.261(3) 0.5124(19) 0.057(6) Uiso 1 1 d . . .
H3A H 0.126(3) 1.025(3) 0.282(2) 0.072(8) Uiso 1 1 d . . .

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
O1 0.0296(5) 0.0301(5) 0.0198(5) -0.0019(4) 0.0010(4) 0.0055(4)
O2 0.0262(5) 0.0247(5) 0.0291(5) 0.0016(4) 0.0019(4) -0.0024(4)
C1 0.0180(6) 0.0184(6) 0.0176(6) 0.0007(5) 0.0032(5) 0.0047(5)
C2 0.0207(6) 0.0168(6) 0.0222(6) 0.0001(5) 0.0035(5) 0.0061(5)
C3 0.0196(6) 0.0164(6) 0.0213(6) 0.0001(5) 0.0030(5) 0.0073(5)
C4 0.0203(6) 0.0209(6) 0.0225(6) 0.0026(5) -0.0001(5) 0.0078(5)
C5 0.0181(6) 0.0196(6) 0.0189(6) 0.0023(5) 0.0044(5) 0.0067(5)
C6 0.0220(6) 0.0169(6) 0.0208(6) 0.0018(5) 0.0029(5) 0.0066(5)
C7 0.0202(6) 0.0184(6) 0.0190(6) 0.0014(5) 0.0025(5) 0.0047(5)
C8 0.0210(6) 0.0195(6) 0.0248(7) -0.0007(5) -0.0029(5) 0.0050(5)
C9 0.0243(7) 0.0207(6) 0.0312(8) 0.0001(6) 0.0034(6) 0.0030(6)
C10 0.0178(6) 0.0199(6) 0.0281(7) -0.0012(5) -0.0002(5) 0.0071(5)
C11 0.0252(7) 0.0173(6) 0.0305(7) -0.0007(5) -0.0024(5) 0.0077(5)
C12 0.0515(10) 0.0242(7) 0.0417(9) 0.0107(7) 0.0134(8) 0.0172(7)
C13 0.0445(10) 0.0330(8) 0.0225(7) -0.0041(6) 0.0045(7) -0.0023(7)
C14 0.0561(11) 0.0314(8) 0.0471(10) 0.0091(7) 0.0214(8) 0.0274(8)
C15 0.0329(9) 0.0533(11) 0.0495(11) -0.0168(9) -0.0031(8) 0.0272(8)
C16 0.0265(8) 0.0511(10) 0.0479(10) 0.0247(8) -0.0006(7) 0.0141(8)

_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
O1 C3 1.2611(16) . ?
O2 C3 1.2737(16) . ?
O2 H2O 0.875(14) . ?
C1 C6 1.4004(18) . ?
C1 C5 1.4067(18) . ?
C1 C3 1.4991(17) . ?
C2 C7 1.3919(18) . ?
C2 C5 1.3935(18) . ?
C2 H1 0.993(17) . ?
C4 C7 1.3898(18) . ?
C4 C6 1.3969(18) . ?
C4 H2 0.984(16) . ?
C5 C10 1.5214(18) . ?
C6 C11 1.5246(18) . ?
C7 C8 1.5211(17) . ?
C8 C9 1.526(2) . ?
C8 C13 1.530(2) . ?
C8 H3 0.980(17) . ?
C9 H5 1.002(18) . ?
C9 H6 0.98(2) . ?
C9 H8 0.988(17) . ?
C10 C16 1.523(2) . ?
C10 C15 1.528(2) . ?
C10 H4 0.990(16) . ?
C11 C12 1.520(2) . ?
C11 C14 1.532(2) . ?
C11 H7 0.990(17) . ?
C12 H9 1.01(2) . ?
C12 H16 0.99(3) . ?
C12 H1A 0.990(19) . ?
C13 H11 0.98(2) . ?
C13 H20 0.97(2) . ?
C13 H2A 1.03(2) . ?
C14 H13 0.98(2) . ?
C14 H15 1.00(2) . ?
C14 H17 1.06(2) . ?
C15 H10 0.97(2) . ?
C15 H19 1.04(2) . ?
C15 H3A 0.97(3) . ?
C16 H12 0.96(2) . ?
C16 H14 0.97(2) . ?
C16 H18 1.01(3) . ?

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
C3 O2 H2O 112.7(12) . . ?
C6 C1 C5 121.42(11) . . ?
C6 C1 C3 119.62(11) . . ?
C5 C1 C3 118.96(11) . . ?
C7 C2 C5 121.98(12) . . ?
C7 C2 H1 119.9(9) . . ?
C5 C2 H1 118.1(9) . . ?
O1 C3 O2 123.60(12) . . ?
O1 C3 C1 119.13(11) . . ?
O2 C3 C1 117.27(11) . . ?
C7 C4 C6 122.18(12) . . ?
C7 C4 H2 118.8(9) . . ?
C6 C4 H2 119.1(9) . . ?
C2 C5 C1 118.14(11) . . ?
C2 C5 C10 119.55(11) . . ?
C1 C5 C10 122.31(11) . . ?
C4 C6 C1 117.98(11) . . ?
C4 C6 C11 119.60(11) . . ?
C1 C6 C11 122.41(11) . . ?
C4 C7 C2 118.31(11) . . ?
C4 C7 C8 120.75(11) . . ?
C2 C7 C8 120.86(11) . . ?
C7 C8 C9 113.00(11) . . ?
C7 C8 C13 109.66(12) . . ?
C9 C8 C13 110.58(12) . . ?
C7 C8 H3 106.9(10) . . ?
C9 C8 H3 108.1(10) . . ?
C13 C8 H3 108.5(10) . . ?
C8 C9 H5 112.6(10) . . ?
C8 C9 H6 113.5(11) . . ?
H5 C9 H6 104.0(14) . . ?
C8 C9 H8 109.0(9) . . ?
H5 C9 H8 108.4(13) . . ?
H6 C9 H8 109.0(14) . . ?
C5 C10 C16 110.26(11) . . ?
C5 C10 C15 112.05(12) . . ?
C16 C10 C15 111.09(15) . . ?
C5 C10 H4 108.7(9) . . ?
C16 C10 H4 109.2(9) . . ?
C15 C10 H4 105.4(9) . . ?
C12 C11 C6 110.66(11) . . ?
C12 C11 C14 110.70(13) . . ?
C6 C11 C14 111.41(12) . . ?
C12 C11 H7 107.9(10) . . ?
C6 C11 H7 109.9(10) . . ?
C14 C11 H7 106.2(10) . . ?
C11 C12 H9 111.7(11) . . ?
C11 C12 H16 110.3(14) . . ?
H9 C12 H16 108.3(17) . . ?
C11 C12 H1A 110.8(10) . . ?
H9 C12 H1A 107.9(15) . . ?
H16 C12 H1A 107.6(17) . . ?
C8 C13 H11 110.8(11) . . ?
C8 C13 H20 111.8(13) . . ?
H11 C13 H20 109.3(16) . . ?
C8 C13 H2A 109.3(12) . . ?
H11 C13 H2A 106.5(16) . . ?
H20 C13 H2A 109.0(17) . . ?
C11 C14 H13 111.5(13) . . ?
C11 C14 H15 110.6(11) . . ?
H13 C14 H15 108.0(17) . . ?
C11 C14 H17 111.1(11) . . ?
H13 C14 H17 107.0(16) . . ?
H15 C14 H17 108.5(15) . . ?
C10 C15 H10 110.3(11) . . ?
C10 C15 H19 111.7(12) . . ?
H10 C15 H19 109.3(17) . . ?
C10 C15 H3A 111.6(15) . . ?
H10 C15 H3A 108.3(18) . . ?
H19 C15 H3A 105.4(18) . . ?
C10 C16 H12 110.4(12) . . ?
C10 C16 H14 110.8(12) . . ?
H12 C16 H14 107.1(16) . . ?
C10 C16 H18 111.8(14) . . ?
H12 C16 H18 107.5(18) . . ?
H14 C16 H18 109.1(17) . . ?

_diffrn_measured_fraction_theta_max 0.912
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.051
#---END