# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_msprm2a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 Cu N3 O5'
_chemical_formula_weight         426.86

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'
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'
Cu Cu 0.3201 1.2651 '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

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

_cell_length_a                   8.7590(3)
_cell_length_b                   9.0172(3)
_cell_length_c                   11.5858(4)
_cell_angle_alpha                95.611(2)
_cell_angle_beta                 111.116(2)
_cell_angle_gamma                95.790(2)
_cell_volume                     840.35(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1945
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      24.32

_exptl_crystal_description       blocks
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             434
_exptl_absorpt_coefficient_mu    1.339
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7571
_exptl_absorpt_correction_T_max  0.8142
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18047
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3664
_reflns_number_gt                3385
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_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)+(0.0554P)²+0.4484P] where P=(Fo²+2Fc²)/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         3664
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_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
C1 C -0.0112(3) 1.1470(3) 0.7624(2) 0.0441(5) Uani 1 1 d . . .
H1 H -0.1200 1.1132 0.7088 0.053 Uiso 1 1 calc R . .
C2 C 0.0218(4) 1.2693(3) 0.8555(2) 0.0569(6) Uani 1 1 d . . .
H2 H -0.0646 1.3160 0.8633 0.068 Uiso 1 1 calc R . .
C3 C 0.1795(4) 1.3203(3) 0.9348(2) 0.0595(7) Uani 1 1 d . . .
H3 H 0.2014 1.4022 0.9966 0.071 Uiso 1 1 calc R . .
C4 C 0.3093(3) 1.2493(3) 0.9231(2) 0.0489(5) Uani 1 1 d . . .
C5 C 0.2658(3) 1.1277(2) 0.82699(18) 0.0384(4) Uani 1 1 d . . .
C6 C 0.3900(3) 1.0486(2) 0.80870(18) 0.0389(4) Uani 1 1 d . . .
C7 C 0.5562(3) 1.0906(3) 0.8872(2) 0.0488(5) Uani 1 1 d . . .
C8 C 0.5971(3) 1.2146(3) 0.9854(2) 0.0606(7) Uani 1 1 d . . .
H8 H 0.7068 1.2432 1.0392 0.073 Uiso 1 1 calc R . .
C9 C 0.4809(4) 1.2897(3) 1.0013(2) 0.0616(7) Uani 1 1 d . . .
H9 H 0.5121 1.3709 1.0650 0.074 Uiso 1 1 calc R . .
C10 C 0.6705(3) 1.0061(3) 0.8641(3) 0.0571(6) Uani 1 1 d . . .
H10 H 0.7822 1.0280 0.9148 0.069 Uiso 1 1 calc R . .
C11 C 0.6164(3) 0.8912(3) 0.7667(3) 0.0576(6) Uani 1 1 d . . .
H11 H 0.6915 0.8354 0.7497 0.069 Uiso 1 1 calc R . .
C12 C 0.4489(3) 0.8575(3) 0.6928(2) 0.0457(5) Uani 1 1 d . . .
H12 H 0.4141 0.7789 0.6267 0.055 Uiso 1 1 calc R . .
C13 C -0.0239(3) 0.6499(2) 0.43240(18) 0.0368(4) Uani 1 1 d . . .
H13 H -0.0054 0.5676 0.3869 0.044 Uiso 1 1 calc R . .
C14 C -0.1913(2) 0.6604(2) 0.41471(18) 0.0350(4) Uani 1 1 d . . .
C15 C -0.2404(2) 0.7867(2) 0.46833(18) 0.0345(4) Uani 1 1 d . . .
C16 C -0.4103(3) 0.7850(3) 0.4420(2) 0.0426(5) Uani 1 1 d . . .
H16 H -0.4463 0.8666 0.4748 0.051 Uiso 1 1 calc R . .
C17 C -0.5240(3) 0.6642(3) 0.3685(2) 0.0506(5) Uani 1 1 d . . .
H17 H -0.6356 0.6646 0.3538 0.061 Uiso 1 1 calc R . .
C18 C -0.4755(3) 0.5420(3) 0.3158(2) 0.0546(6) Uani 1 1 d . . .
H18 H -0.5541 0.4615 0.2659 0.066 Uiso 1 1 calc R . .
C19 C -0.3127(3) 0.5401(3) 0.3373(2) 0.0462(5) Uani 1 1 d . . .
H19 H -0.2807 0.4587 0.3007 0.055 Uiso 1 1 calc R . .
N1 N 0.1086(2) 1.07769(19) 0.74824(15) 0.0362(4) Uani 1 1 d . . .
N2 N 0.3376(2) 0.9333(2) 0.71319(16) 0.0376(4) Uani 1 1 d . . .
N3 N -0.0258(2) 0.6942(2) 0.79406(18) 0.0446(4) Uani 1 1 d . . .
O2 O 0.10086(18) 0.73892(17) 0.50231(13) 0.0388(3) Uani 1 1 d . . .
O1 O -0.13713(18) 0.90422(17) 0.53701(15) 0.0422(3) Uani 1 1 d . . .
O3 O 0.0656(3) 0.6999(2) 0.73481(19) 0.0608(5) Uani 1 1 d . . .
O4 O -0.0135(3) 0.8102(3) 0.8696(2) 0.0795(6) Uani 1 1 d . . .
O5 O -0.1265(4) 0.5890(3) 0.7788(4) 0.1343(15) Uani 1 1 d . . .
Cu1 Cu 0.09207(3) 0.90213(3) 0.62266(2) 0.03482(10) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.324(3) . ?
C1 C2 1.393(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.356(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(3) . ?
C4 C9 1.434(4) . ?
C5 N1 1.349(3) . ?
C5 C6 1.424(3) . ?
C6 N2 1.353(3) . ?
C6 C7 1.399(3) . ?
C7 C10 1.401(4) . ?
C7 C8 1.432(4) . ?
C8 C9 1.334(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.363(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9300 . ?
C12 N2 1.320(3) . ?
C12 H12 0.9300 . ?
C13 O2 1.246(3) . ?
C13 C14 1.420(3) . ?
C13 H13 0.9300 . ?
C14 C19 1.415(3) . ?
C14 C15 1.421(3) . ?
C15 O1 1.303(2) . ?
C15 C16 1.405(3) . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.358(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N1 Cu1 1.9990(17) . ?
N2 Cu1 1.9996(17) . ?
N3 O5 1.181(3) . ?
N3 O3 1.229(3) . ?
N3 O4 1.266(3) . ?
O2 Cu1 1.9532(14) . ?
O1 Cu1 1.8951(15) . ?
O3 Cu1 2.3793(19) . ?

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
N1 C1 C2 121.7(2) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 116.5(2) . . ?
C5 C4 C9 117.8(3) . . ?
C3 C4 C9 125.7(2) . . ?
N1 C5 C4 123.4(2) . . ?
N1 C5 C6 116.36(19) . . ?
C4 C5 C6 120.2(2) . . ?
N2 C6 C7 123.1(2) . . ?
N2 C6 C5 116.43(18) . . ?
C7 C6 C5 120.5(2) . . ?
C6 C7 C10 117.0(2) . . ?
C6 C7 C8 118.2(3) . . ?
C10 C7 C8 124.8(2) . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C4 122.1(2) . . ?
C8 C9 H9 119.0 . . ?
C4 C9 H9 119.0 . . ?
C11 C10 C7 119.3(2) . . ?
C11 C10 H10 120.3 . . ?
C7 C10 H10 120.3 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N2 C12 C11 122.3(2) . . ?
N2 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
O2 C13 C14 127.08(19) . . ?
O2 C13 H13 116.5 . . ?
C14 C13 H13 116.5 . . ?
C19 C14 C13 117.38(19) . . ?
C19 C14 C15 119.7(2) . . ?
C13 C14 C15 122.94(18) . . ?
O1 C15 C16 118.93(19) . . ?
O1 C15 C14 123.48(19) . . ?
C16 C15 C14 117.56(18) . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 121.2(2) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C14 120.9(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C1 N1 C5 118.47(19) . . ?
C1 N1 Cu1 128.88(15) . . ?
C5 N1 Cu1 112.65(15) . . ?
C12 N2 C6 118.31(19) . . ?
C12 N2 Cu1 129.23(16) . . ?
C6 N2 Cu1 112.46(15) . . ?
O5 N3 O3 122.6(3) . . ?
O5 N3 O4 120.4(3) . . ?
O3 N3 O4 117.0(2) . . ?
C13 O2 Cu1 122.79(14) . . ?
C15 O1 Cu1 123.78(13) . . ?
N3 O3 Cu1 122.82(15) . . ?
O1 Cu1 O2 93.37(6) . . ?
O1 Cu1 N1 91.95(7) . . ?
O2 Cu1 N1 173.71(6) . . ?
O1 Cu1 N2 171.43(7) . . ?
O2 Cu1 N2 92.24(7) . . ?
N1 Cu1 N2 82.10(7) . . ?
O1 Cu1 O3 97.00(7) . . ?
O2 Cu1 O3 82.34(6) . . ?
N1 Cu1 O3 100.33(7) . . ?
N2 Cu1 O3 90.16(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C2 C3 C4 C9 -179.0(3) . . . . ?
C3 C4 C5 N1 -0.3(3) . . . . ?
C9 C4 C5 N1 179.2(2) . . . . ?
C3 C4 C5 C6 -179.8(2) . . . . ?
C9 C4 C5 C6 -0.3(3) . . . . ?
N1 C5 C6 N2 0.9(3) . . . . ?
C4 C5 C6 N2 -179.52(18) . . . . ?
N1 C5 C6 C7 -178.90(18) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
N2 C6 C7 C10 -0.7(3) . . . . ?
C5 C6 C7 C10 179.1(2) . . . . ?
N2 C6 C7 C8 -179.9(2) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C9 -0.9(4) . . . . ?
C10 C7 C8 C9 180.0(3) . . . . ?
C7 C8 C9 C4 1.3(4) . . . . ?
C5 C4 C9 C8 -0.6(4) . . . . ?
C3 C4 C9 C8 178.8(3) . . . . ?
C6 C7 C10 C11 1.4(4) . . . . ?
C8 C7 C10 C11 -179.4(2) . . . . ?
C7 C10 C11 C12 -1.1(4) . . . . ?
C10 C11 C12 N2 0.0(4) . . . . ?
O2 C13 C14 C19 -175.5(2) . . . . ?
O2 C13 C14 C15 6.2(3) . . . . ?
C19 C14 C15 O1 -177.5(2) . . . . ?
C13 C14 C15 O1 0.8(3) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
C13 C14 C15 C16 178.85(19) . . . . ?
O1 C15 C16 C17 179.1(2) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C15 C16 C17 C18 -1.4(4) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C17 C18 C19 C14 1.1(4) . . . . ?
C13 C14 C19 C18 -180.0(2) . . . . ?
C15 C14 C19 C18 -1.5(3) . . . . ?
C2 C1 N1 C5 0.2(3) . . . . ?
C2 C1 N1 Cu1 -179.84(17) . . . . ?
C4 C5 N1 C1 0.0(3) . . . . ?
C6 C5 N1 C1 179.49(18) . . . . ?
C4 C5 N1 Cu1 -179.98(16) . . . . ?
C6 C5 N1 Cu1 -0.5(2) . . . . ?
C11 C12 N2 C6 0.8(3) . . . . ?
C11 C12 N2 Cu1 -178.39(18) . . . . ?
C7 C6 N2 C12 -0.4(3) . . . . ?
C5 C6 N2 C12 179.74(19) . . . . ?
C7 C6 N2 Cu1 178.90(16) . . . . ?
C5 C6 N2 Cu1 -0.9(2) . . . . ?
C14 C13 O2 Cu1 8.8(3) . . . . ?
C16 C15 O1 Cu1 159.91(16) . . . . ?
C14 C15 O1 Cu1 -22.0(3) . . . . ?
O5 N3 O3 Cu1 126.6(3) . . . . ?
O4 N3 O3 Cu1 -50.2(3) . . . . ?
C15 O1 Cu1 O2 27.96(17) . . . . ?
C15 O1 Cu1 N1 -155.39(17) . . . . ?
C15 O1 Cu1 N2 158.8(4) . . . . ?
C15 O1 Cu1 O3 -54.73(17) . . . . ?
C13 O2 Cu1 O1 -21.46(17) . . . . ?
C13 O2 Cu1 N1 -169.2(5) . . . . ?
C13 O2 Cu1 N2 165.02(16) . . . . ?
C13 O2 Cu1 O3 75.15(16) . . . . ?
C1 N1 Cu1 O1 6.22(19) . . . . ?
C5 N1 Cu1 O1 -173.85(14) . . . . ?
C1 N1 Cu1 O2 154.0(5) . . . . ?
C5 N1 Cu1 O2 -26.0(6) . . . . ?
C1 N1 Cu1 N2 -179.97(19) . . . . ?
C5 N1 Cu1 N2 -0.04(14) . . . . ?
C1 N1 Cu1 O3 -91.26(19) . . . . ?
C5 N1 Cu1 O3 88.68(14) . . . . ?
C12 N2 Cu1 O1 -133.9(4) . . . . ?
C6 N2 Cu1 O1 46.8(5) . . . . ?
C12 N2 Cu1 O2 -3.0(2) . . . . ?
C6 N2 Cu1 O2 177.78(14) . . . . ?
C12 N2 Cu1 N1 179.8(2) . . . . ?
C6 N2 Cu1 N1 0.53(14) . . . . ?
C12 N2 Cu1 O3 79.4(2) . . . . ?
C6 N2 Cu1 O3 -99.88(14) . . . . ?
N3 O3 Cu1 O1 -49.0(2) . . . . ?
N3 O3 Cu1 O2 -141.5(2) . . . . ?
N3 O3 Cu1 N1 44.3(2) . . . . ?
N3 O3 Cu1 N2 126.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 850169'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2mptmrev

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Cl Cu N2 O6'
_chemical_formula_weight         440.28

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'
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'
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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.483(4)
_cell_length_b                   9.426(5)
_cell_length_c                   11.880(6)
_cell_angle_alpha                78.045(8)
_cell_angle_beta                 69.619(8)
_cell_angle_gamma                82.745(8)
_cell_volume                     869.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1434
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      26.43

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            GREEN
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             446
_exptl_absorpt_coefficient_mu    1.448
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7135
_exptl_absorpt_correction_T_max  0.8454
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 diffractometer'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7226
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0423
_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         1.86
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3717
_reflns_number_gt                3198
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'BRUKER SHELXTL'

_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)+(0.0594P)²+0.8607P] 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         3717
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.001
_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 0.51671(6) 0.89848(5) 0.89067(4) 0.03516(17) Uani 1 1 d . . .
Cl1 Cl 0.77885(12) 0.69090(10) 0.66237(9) 0.0407(2) Uani 1 1 d . . .
N2 N 0.6179(4) 1.0625(3) 0.7576(3) 0.0346(7) Uani 1 1 d . . .
N1 N 0.3578(4) 0.9151(3) 0.7980(3) 0.0367(7) Uani 1 1 d . . .
O1 O 0.6680(3) 0.9056(3) 0.9761(3) 0.0403(6) Uani 1 1 d . . .
O2 O 0.4034(4) 0.7328(3) 1.0074(2) 0.0438(7) Uani 1 1 d . . .
O3 O 0.7076(6) 0.6951(4) 0.7906(3) 0.0864(13) Uani 1 1 d . . .
O4 O 0.9016(6) 0.5771(4) 0.6458(5) 0.0958(14) Uani 1 1 d . . .
O5 O 0.8512(5) 0.8254(4) 0.6015(3) 0.0659(10) Uani 1 1 d . . .
O6 O 0.6486(6) 0.6700(5) 0.6200(5) 0.1013(16) Uani 1 1 d . . .
C1 C 0.7129(5) 0.7922(4) 1.0470(3) 0.0365(8) Uani 1 1 d . . .
C2 C 0.8590(5) 0.7956(5) 1.0760(4) 0.0467(10) Uani 1 1 d . . .
H2 H 0.9231 0.8767 1.0438 0.056 Uiso 1 1 calc R . .
C3 C 0.9092(6) 0.6816(5) 1.1509(5) 0.0586(12) Uani 1 1 d . . .
H3 H 1.0080 0.6863 1.1671 0.070 Uiso 1 1 calc R . .
C4 C 0.8162(7) 0.5595(6) 1.2032(5) 0.0678(14) Uani 1 1 d . . .
H4 H 0.8519 0.4834 1.2542 0.081 Uiso 1 1 calc R . .
C5 C 0.6721(6) 0.5522(5) 1.1790(4) 0.0552(12) Uani 1 1 d . . .
H5 H 0.6080 0.4716 1.2154 0.066 Uiso 1 1 calc R . .
C6 C 0.6185(5) 0.6654(4) 1.0994(4) 0.0400(9) Uani 1 1 d . . .
C7 C 0.4670(5) 0.6488(4) 1.0785(4) 0.0421(9) Uani 1 1 d . . .
H7 H 0.4091 0.5665 1.1224 0.051 Uiso 1 1 calc R . .
C8 C 0.7553(5) 1.1302(4) 0.7435(4) 0.0413(9) Uani 1 1 d . . .
H8 H 0.8140 1.0977 0.7980 0.050 Uiso 1 1 calc R . .
C9 C 0.8124(6) 1.2456(5) 0.6515(4) 0.0493(10) Uani 1 1 d . . .
H9 H 0.9094 1.2892 0.6428 0.059 Uiso 1 1 calc R . .
C10 C 0.7240(6) 1.2957(5) 0.5726(4) 0.0538(11) Uani 1 1 d . . .
H10 H 0.7589 1.3755 0.5112 0.065 Uiso 1 1 calc R . .
C11 C 0.5832(6) 1.2271(5) 0.5846(4) 0.0489(10) Uani 1 1 d . . .
H11 H 0.5225 1.2597 0.5314 0.059 Uiso 1 1 calc R . .
C12 C 0.5336(5) 1.1080(4) 0.6780(3) 0.0353(8) Uani 1 1 d . . .
C14 C 0.2907(6) 1.0442(5) 0.6244(4) 0.0466(10) Uani 1 1 d . . .
H14 H 0.3137 1.1174 0.5561 0.056 Uiso 1 1 calc R . .
C15 C 0.1576(6) 0.9572(5) 0.6525(4) 0.0512(11) Uani 1 1 d . . .
H15 H 0.0904 0.9714 0.6034 0.061 Uiso 1 1 calc R . .
C13 C 0.3891(5) 1.0214(4) 0.6984(3) 0.0380(8) Uani 1 1 d . . .
C16 C 0.1260(6) 0.8497(5) 0.7537(4) 0.0508(11) Uani 1 1 d . . .
H16 H 0.0368 0.7904 0.7745 0.061 Uiso 1 1 calc R . .
C17 C 0.2292(5) 0.8313(4) 0.8240(4) 0.0444(9) Uani 1 1 d . . .
H17 H 0.2086 0.7578 0.8921 0.053 Uiso 1 1 calc R . .


_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 1.908(3) . ?
Cu1 O2 1.960(3) . ?
Cu1 N1 1.991(3) . ?
Cu1 N2 2.001(3) . ?
Cl1 O4 1.392(4) . ?
Cl1 O6 1.413(4) . ?
Cl1 O5 1.419(3) . ?
Cl1 O3 1.437(4) . ?
N2 C8 1.342(5) . ?
N2 C12 1.348(5) . ?
N1 C17 1.339(5) . ?
N1 C13 1.353(5) . ?
O1 C1 1.320(4) . ?
O2 C7 1.250(5) . ?
C1 C2 1.404(6) . ?
C1 C6 1.430(5) . ?
C2 C3 1.371(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.413(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.424(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.480(5) . ?
C14 C13 1.380(6) . ?
C14 C15 1.384(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(6) . ?
C16 H16 0.9300 . ?
C17 H17 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 O2 93.38(12) . . ?
O1 Cu1 N1 173.62(12) . . ?
O2 Cu1 N1 91.63(13) . . ?
O1 Cu1 N2 93.62(12) . . ?
O2 Cu1 N2 172.78(12) . . ?
N1 Cu1 N2 81.51(13) . . ?
O4 Cl1 O6 111.0(3) . . ?
O4 Cl1 O5 110.4(3) . . ?
O6 Cl1 O5 110.1(2) . . ?
O4 Cl1 O3 108.4(3) . . ?
O6 Cl1 O3 108.5(3) . . ?
O5 Cl1 O3 108.4(2) . . ?
C8 N2 C12 119.0(3) . . ?
C8 N2 Cu1 126.4(3) . . ?
C12 N2 Cu1 114.5(2) . . ?
C17 N1 C13 118.9(3) . . ?
C17 N1 Cu1 126.4(3) . . ?
C13 N1 Cu1 114.6(3) . . ?
C1 O1 Cu1 123.7(2) . . ?
C7 O2 Cu1 123.6(3) . . ?
O1 C1 C2 119.1(4) . . ?
O1 C1 C6 123.8(4) . . ?
C2 C1 C6 117.1(4) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 121.6(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 119.3(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 117.4(4) . . ?
C5 C6 C1 119.8(4) . . ?
C7 C6 C1 122.8(4) . . ?
O2 C7 C6 127.1(4) . . ?
O2 C7 H7 116.5 . . ?
C6 C7 H7 116.5 . . ?
N2 C8 C9 122.4(4) . . ?
N2 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C10 C9 C8 118.9(4) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 119.8(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 118.8(4) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
N2 C12 C11 121.1(4) . . ?
N2 C12 C13 114.6(3) . . ?
C11 C12 C13 124.4(4) . . ?
C13 C14 C15 119.5(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 119.3(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N1 C13 C14 121.1(4) . . ?
N1 C13 C12 114.6(3) . . ?
C14 C13 C12 124.3(4) . . ?
C15 C16 C17 118.7(4) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N1 C17 C16 122.6(4) . . ?
N1 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.092
_database_code_depnum_ccdc_archive 'CCDC 850170'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3mptmm

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 Cl Cu N2 O6'
_chemical_formula_weight         520.41

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'
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'
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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.315(5)
_cell_length_b                   10.880(6)
_cell_length_c                   11.981(6)
_cell_angle_alpha                100.812(8)
_cell_angle_beta                 110.455(8)
_cell_angle_gamma                94.285(8)
_cell_volume                     1104.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1918
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      25.65
_exptl_crystal_description       blocks
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             534
_exptl_absorpt_coefficient_mu    1.154
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6951
_exptl_absorpt_correction_T_max  0.8740
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8995
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         26.99
_reflns_number_total             4698
_reflns_number_gt                3740
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'BRUKER SHELXTL'

_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)+(0.0904P)²+0.6119P] where P=(Fo²+2Fc²)/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         4698
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1664
_refine_ls_wR_factor_gt          0.1519
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_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 0.58280(5) 0.90963(4) 0.60771(4) 0.04319(19) Uani 1 1 d . . .
Cl1 Cl 0.54712(12) 0.66799(10) 0.76863(10) 0.0530(3) Uani 1 1 d . . .
N1 N 0.6267(4) 1.0693(3) 0.7347(3) 0.0419(7) Uani 1 1 d . . .
N2 N 0.8082(4) 0.9101(3) 0.6928(3) 0.0455(8) Uani 1 1 d . . .
O1 O 0.3737(3) 0.9330(3) 0.5311(2) 0.0470(7) Uani 1 1 d . . .
O2 O 0.5574(3) 0.7471(3) 0.4955(2) 0.0511(7) Uani 1 1 d . . .
O3 O 0.5379(4) 0.7957(3) 0.7532(3) 0.0691(9) Uani 1 1 d . . .
O5 O 0.6940(4) 0.6361(4) 0.7738(4) 0.0889(12) Uani 1 1 d . . .
O4 O 0.5273(6) 0.6631(4) 0.8793(4) 0.0937(13) Uani 1 1 d . . .
O6 O 0.4287(4) 0.5826(3) 0.6689(3) 0.0760(10) Uani 1 1 d . . .
C1 C 0.2592(5) 0.8396(4) 0.4685(3) 0.0423(9) Uani 1 1 d . . .
C2 C 0.1069(5) 0.8652(4) 0.4450(4) 0.0515(10) Uani 1 1 d . . .
H2 H 0.0903 0.9461 0.4740 0.062 Uiso 1 1 calc R . .
C3 C -0.0170(5) 0.7715(5) 0.3796(5) 0.0670(13) Uani 1 1 d . . .
H3 H -0.1167 0.7904 0.3651 0.080 Uiso 1 1 calc R . .
C4 C 0.0020(6) 0.6497(5) 0.3344(5) 0.0750(15) Uani 1 1 d . . .
H4 H -0.0837 0.5874 0.2903 0.090 Uiso 1 1 calc R . .
C5 C 0.1482(6) 0.6226(4) 0.3555(4) 0.0633(12) Uani 1 1 d . . .
H5 H 0.1616 0.5410 0.3251 0.076 Uiso 1 1 calc R . .
C6 C 0.2798(5) 0.7153(4) 0.4224(3) 0.0440(9) Uani 1 1 d . . .
C7 C 0.4283(5) 0.6800(4) 0.4376(4) 0.0519(10) Uani 1 1 d . . .
H7 H 0.4292 0.5973 0.3998 0.062 Uiso 1 1 calc R . .
C8 C 0.5298(5) 1.1475(4) 0.7517(3) 0.0442(9) Uani 1 1 d . . .
H8 H 0.4254 1.1257 0.7018 0.053 Uiso 1 1 calc R . .
C9 C 0.5765(5) 1.2610(4) 0.8408(3) 0.0461(9) Uani 1 1 d . . .
C10 C 0.7312(5) 1.2962(4) 0.9147(4) 0.0491(10) Uani 1 1 d . . .
C11 C 0.8366(5) 1.2121(4) 0.8995(4) 0.0473(9) Uani 1 1 d . . .
C12 C 0.7786(4) 1.1013(4) 0.8076(3) 0.0424(9) Uani 1 1 d . . .
C13 C 0.9990(5) 1.2317(5) 0.9718(4) 0.0595(12) Uani 1 1 d . . .
H13 H 1.0416 1.3042 1.0344 0.071 Uiso 1 1 calc R . .
C14 C 1.0928(5) 1.1473(5) 0.9514(4) 0.0623(13) Uani 1 1 d . . .
H14 H 1.1977 1.1640 1.0004 0.075 Uiso 1 1 calc R . .
C15 C 1.0357(5) 1.0344(4) 0.8576(4) 0.0517(10) Uani 1 1 d . . .
C16 C 0.8774(4) 1.0123(4) 0.7851(4) 0.0442(9) Uani 1 1 d . . .
C17 C 1.1281(5) 0.9411(5) 0.8304(4) 0.0537(11) Uani 1 1 d . . .
C18 C 1.0551(5) 0.8355(5) 0.7373(4) 0.0577(11) Uani 1 1 d . . .
C19 C 0.8957(5) 0.8241(4) 0.6702(4) 0.0519(10) Uani 1 1 d . . .
H19 H 0.8484 0.7531 0.6067 0.062 Uiso 1 1 calc R . .
C20 C 0.4529(6) 1.3419(4) 0.8469(4) 0.0585(11) Uani 1 1 d . . .
H20A H 0.4693 1.3767 0.9309 0.088 Uiso 1 1 calc R . .
H20B H 0.3526 1.2908 0.8070 0.088 Uiso 1 1 calc R . .
H20C H 0.4586 1.4094 0.8065 0.088 Uiso 1 1 calc R . .
C21 C 0.7839(6) 1.4216(5) 1.0078(5) 0.0717(14) Uani 1 1 d . . .
H21A H 0.7740 1.4896 0.9661 0.108 Uiso 1 1 calc R . .
H21B H 0.8903 1.4263 1.0597 0.108 Uiso 1 1 calc R . .
H21C H 0.7208 1.4284 1.0565 0.108 Uiso 1 1 calc R . .
C22 C 1.2992(5) 0.9608(6) 0.9033(5) 0.0784(16) Uani 1 1 d . . .
H22A H 1.3379 0.8818 0.8922 0.118 Uiso 1 1 calc R . .
H22B H 1.3179 0.9916 0.9884 0.118 Uiso 1 1 calc R . .
H22C H 1.3513 1.0214 0.8760 0.118 Uiso 1 1 calc R . .
C23 C 1.1382(6) 0.7285(6) 0.7016(5) 0.0741(15) Uani 1 1 d . . .
H23A H 1.2028 0.7568 0.6612 0.111 Uiso 1 1 calc R . .
H23B H 1.0631 0.6575 0.6473 0.111 Uiso 1 1 calc R . .
H23C H 1.2012 0.7036 0.7738 0.111 Uiso 1 1 calc R . .


_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 1.901(3) . ?
Cu1 O2 1.953(3) . ?
Cu1 N2 1.987(3) . ?
Cu1 N1 1.992(3) . ?
Cl1 O4 1.411(4) . ?
Cl1 O6 1.420(3) . ?
Cl1 O5 1.420(4) . ?
Cl1 O3 1.440(3) . ?
N1 C8 1.325(5) . ?
N1 C12 1.355(5) . ?
N2 C19 1.336(5) . ?
N2 C16 1.344(5) . ?
O1 C1 1.314(5) . ?
O2 C7 1.247(5) . ?
C1 C2 1.407(5) . ?
C1 C6 1.415(6) . ?
C2 C3 1.370(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.422(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.398(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(6) . ?
C9 C20 1.514(6) . ?
C10 C11 1.424(6) . ?
C10 C21 1.514(6) . ?
C11 C12 1.395(5) . ?
C11 C13 1.432(6) . ?
C12 C16 1.438(6) . ?
C13 C14 1.360(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.422(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.400(5) . ?
C15 C17 1.442(6) . ?
C17 C18 1.378(7) . ?
C17 C22 1.502(6) . ?
C18 C19 1.402(6) . ?
C18 C23 1.523(7) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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 93.69(11) . . ?
O1 Cu1 N2 172.38(13) . . ?
O2 Cu1 N2 92.80(13) . . ?
O1 Cu1 N1 91.69(12) . . ?
O2 Cu1 N1 174.06(12) . . ?
N2 Cu1 N1 82.02(13) . . ?
O4 Cl1 O6 110.3(3) . . ?
O4 Cl1 O5 110.3(3) . . ?
O6 Cl1 O5 109.3(2) . . ?
O4 Cl1 O3 107.3(2) . . ?
O6 Cl1 O3 109.9(2) . . ?
O5 Cl1 O3 109.8(2) . . ?
C8 N1 C12 118.2(3) . . ?
C8 N1 Cu1 128.7(3) . . ?
C12 N1 Cu1 113.0(3) . . ?
C19 N2 C16 117.9(4) . . ?
C19 N2 Cu1 128.8(3) . . ?
C16 N2 Cu1 113.3(3) . . ?
C1 O1 Cu1 123.7(2) . . ?
C7 O2 Cu1 122.3(3) . . ?
O1 C1 C2 117.9(3) . . ?
O1 C1 C6 124.0(4) . . ?
C2 C1 C6 118.1(4) . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.9(4) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 118.8(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 119.1(4) . . ?
C5 C6 C7 118.1(4) . . ?
C1 C6 C7 122.8(4) . . ?
O2 C7 C6 127.6(4) . . ?
O2 C7 H7 116.2 . . ?
C6 C7 H7 116.2 . . ?
N1 C8 C9 123.4(4) . . ?
N1 C8 H8 118.3 . . ?
C9 C8 H8 118.3 . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 C20 123.4(4) . . ?
C8 C9 C20 117.2(4) . . ?
C9 C10 C11 118.1(4) . . ?
C9 C10 C21 119.7(4) . . ?
C11 C10 C21 122.2(4) . . ?
C12 C11 C10 118.1(4) . . ?
C12 C11 C13 116.7(4) . . ?
C10 C11 C13 125.2(4) . . ?
N1 C12 C11 122.9(4) . . ?
N1 C12 C16 115.5(3) . . ?
C11 C12 C16 121.7(4) . . ?
C14 C13 C11 121.8(4) . . ?
C14 C13 H13 119.1 . . ?
C11 C13 H13 119.1 . . ?
C13 C14 C15 122.2(4) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C16 C15 C14 117.5(4) . . ?
C16 C15 C17 117.3(4) . . ?
C14 C15 C17 125.2(4) . . ?
N2 C16 C15 123.8(4) . . ?
N2 C16 C12 116.1(3) . . ?
C15 C16 C12 120.1(4) . . ?
C18 C17 C15 118.3(4) . . ?
C18 C17 C22 122.0(4) . . ?
C15 C17 C22 119.8(5) . . ?
C17 C18 C19 119.3(4) . . ?
C17 C18 C23 123.5(4) . . ?
C19 C18 C23 117.1(5) . . ?
N2 C19 C18 123.4(4) . . ?
N2 C19 H19 118.3 . . ?
C18 C19 H19 118.3 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C21 H21A 109.5 . . ?
C10 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C10 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.096
_database_code_depnum_ccdc_archive 'CCDC 850171'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_24mprlm

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 Cl Cu N2 O6'
_chemical_formula_weight         464.30

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'
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'
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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.1505(16)
_cell_length_b                   9.2236(16)
_cell_length_c                   11.473(2)
_cell_angle_alpha                95.496(3)
_cell_angle_beta                 111.093(3)
_cell_angle_gamma                97.275(3)
_cell_volume                     885.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3101
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.18
_exptl_crystal_description       Prism
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             470
_exptl_absorpt_coefficient_mu    1.427
_exptl_absorpt_correction_type   Multi-SCAN
_exptl_absorpt_correction_T_min  0.8252
_exptl_absorpt_correction_T_max  0.9451
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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 DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7344
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3772
_reflns_number_gt                3456
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'BRUKER SHELXTL'

_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)+(0.0324P)²+3.0640P] 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         3772
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_restrained_S_all      1.231
_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
Cl1 Cl -0.03225(11) 0.19303(11) 0.30768(9) 0.0149(2) Uani 1 1 d . . .
O1 O -0.1255(3) 0.4012(3) 0.0290(3) 0.0161(6) Uani 1 1 d . . .
O2 O 0.1024(3) 0.2406(3) -0.0043(3) 0.0158(6) Uani 1 1 d . . .
O3 O 0.0713(4) 0.2098(3) 0.2369(3) 0.0221(7) Uani 1 1 d . . .
O4 O 0.0281(4) 0.0995(4) 0.3999(3) 0.0269(8) Uani 1 1 d . . .
O5 O -0.0331(4) 0.3358(3) 0.3689(3) 0.0246(7) Uani 1 1 d . . .
O6 O -0.1898(4) 0.1283(4) 0.2220(3) 0.0350(9) Uani 1 1 d . . .
Cu1 Cu 0.09729(6) 0.40599(5) 0.11302(5) 0.01236(15) Uani 1 1 d . . .
N1 N 0.1151(4) 0.5721(4) 0.2451(3) 0.0133(7) Uani 1 1 d . . .
N2 N 0.3339(4) 0.4373(4) 0.2057(3) 0.0142(7) Uani 1 1 d . . .
C1 C 0.0001(5) 0.6367(5) 0.2617(4) 0.0175(9) Uani 1 1 d . . .
C2 C 0.0331(6) 0.7574(5) 0.3557(4) 0.0207(9) Uani 1 1 d . . .
C3 C 0.1865(6) 0.8110(5) 0.4350(4) 0.0215(9) Uani 1 1 d . . .
C4 C 0.3103(5) 0.7439(5) 0.4217(4) 0.0178(9) Uani 1 1 d . . .
C5 C 0.2676(5) 0.6234(5) 0.3242(4) 0.0155(8) Uani 1 1 d . . .
C6 C 0.4768(6) 0.7895(5) 0.5002(4) 0.0255(10) Uani 1 1 d . . .
C7 C 0.5879(6) 0.7171(5) 0.4822(5) 0.0249(10) Uani 1 1 d . . .
C8 C 0.5475(5) 0.5953(5) 0.3823(4) 0.0189(9) Uani 1 1 d . . .
C9 C 0.3859(5) 0.5501(4) 0.3038(4) 0.0144(8) Uani 1 1 d . . .
C10 C 0.6564(5) 0.5159(5) 0.3568(4) 0.0233(10) Uani 1 1 d . . .
C11 C 0.6029(5) 0.4023(5) 0.2568(5) 0.0227(10) Uani 1 1 d . . .
C12 C 0.4398(5) 0.3654(5) 0.1829(4) 0.0176(9) Uani 1 1 d . . .
H12 H 0.4048 0.2880 0.1158 0.021 Uiso 1 1 calc R . .
C13 C -0.2265(5) 0.2806(4) -0.0355(4) 0.0141(8) Uani 1 1 d . . .
C14 C -0.3893(5) 0.2746(5) -0.0599(4) 0.0176(9) Uani 1 1 d . . .
H14 H -0.4231 0.3556 -0.0291 0.021 Uiso 1 1 calc R . .
C15 C -0.4993(5) 0.1521(5) -0.1280(4) 0.0220(9) Uani 1 1 d . . .
C16 C -0.4540(5) 0.0287(5) -0.1785(5) 0.0241(10) Uani 1 1 d . . .
C17 C -0.2975(5) 0.0313(5) -0.1587(4) 0.0194(9) Uani 1 1 d . . .
C18 C -0.1803(5) 0.1544(5) -0.0873(4) 0.0153(8) Uani 1 1 d . . .
C19 C -0.0188(5) 0.1479(5) -0.0705(4) 0.0166(9) Uani 1 1 d . . .
H6 H 0.496(5) 0.868(5) 0.562(4) 0.016(12) Uiso 1 1 d . . .
H2 H -0.050(5) 0.797(5) 0.361(4) 0.014(11) Uiso 1 1 d . . .
H15 H -0.607(6) 0.147(5) -0.142(4) 0.020(12) Uiso 1 1 d . . .
H11 H 0.670(6) 0.347(6) 0.242(5) 0.023(13) Uiso 1 1 d . . .
H17 H -0.259(5) -0.044(5) -0.187(4) 0.011(11) Uiso 1 1 d . . .
H1 H -0.101(6) 0.599(5) 0.210(5) 0.022(13) Uiso 1 1 d . . .
H16 H -0.527(6) -0.056(6) -0.221(5) 0.022(13) Uiso 1 1 d . . .
H10 H 0.761(7) 0.538(6) 0.402(5) 0.030(14) Uiso 1 1 d . . .
H7 H 0.686(7) 0.748(6) 0.522(5) 0.035(15) Uiso 1 1 d . . .
H3 H 0.209(7) 0.889(7) 0.492(6) 0.041(17) Uiso 1 1 d . . .
H18 H -0.006(6) 0.063(6) -0.115(5) 0.029(14) Uiso 1 1 d . . .


_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
Cl1 O4 1.429(3) . ?
Cl1 O6 1.432(3) . ?
Cl1 O5 1.435(3) . ?
Cl1 O3 1.456(3) . ?
O1 C13 1.315(5) . ?
O1 Cu1 1.908(3) . ?
O2 C19 1.251(5) . ?
O2 Cu1 1.952(3) . ?
O3 Cu1 2.446(3) . ?
Cu1 N1 1.997(3) . ?
Cu1 N2 2.007(3) . ?
N1 C1 1.334(5) . ?
N1 C5 1.354(5) . ?
N2 C12 1.326(5) . ?
N2 C9 1.357(5) . ?
C1 C2 1.394(6) . ?
C1 H1 0.90(5) . ?
C2 C3 1.365(7) . ?
C2 H2 0.91(5) . ?
C3 C4 1.404(6) . ?
C3 H3 0.88(6) . ?
C4 C5 1.406(6) . ?
C4 C6 1.445(6) . ?
C5 C9 1.421(6) . ?
C6 C7 1.349(7) . ?
C6 H6 0.91(5) . ?
C7 C8 1.434(7) . ?
C7 H7 0.85(6) . ?
C8 C10 1.403(7) . ?
C8 C9 1.409(5) . ?
C10 C11 1.374(7) . ?
C10 H10 0.89(5) . ?
C11 C12 1.403(6) . ?
C11 H11 0.90(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.406(6) . ?
C13 C18 1.435(6) . ?
C14 C15 1.371(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.403(7) . ?
C15 H15 0.94(5) . ?
C16 C17 1.364(6) . ?
C16 H16 0.92(5) . ?
C17 C18 1.411(6) . ?
C17 H17 0.90(5) . ?
C18 C19 1.429(6) . ?
C19 H18 0.94(5) . ?

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
O4 Cl1 O6 110.4(2) . . ?
O4 Cl1 O5 110.0(2) . . ?
O6 Cl1 O5 109.9(2) . . ?
O4 Cl1 O3 108.45(19) . . ?
O6 Cl1 O3 109.0(2) . . ?
O5 Cl1 O3 109.04(19) . . ?
C13 O1 Cu1 123.5(3) . . ?
C19 O2 Cu1 122.7(3) . . ?
Cl1 O3 Cu1 127.21(18) . . ?
O1 Cu1 O2 93.72(12) . . ?
O1 Cu1 N1 92.22(13) . . ?
O2 Cu1 N1 173.87(13) . . ?
O1 Cu1 N2 173.16(13) . . ?
O2 Cu1 N2 91.91(13) . . ?
N1 Cu1 N2 82.26(14) . . ?
O1 Cu1 O3 95.83(12) . . ?
O2 Cu1 O3 82.35(11) . . ?
N1 Cu1 O3 95.57(12) . . ?
N2 Cu1 O3 88.76(12) . . ?
C1 N1 C5 118.8(4) . . ?
C1 N1 Cu1 128.8(3) . . ?
C5 N1 Cu1 112.4(3) . . ?
C12 N2 C9 118.6(4) . . ?
C12 N2 Cu1 129.2(3) . . ?
C9 N2 Cu1 112.2(3) . . ?
N1 C1 C2 121.9(4) . . ?
N1 C1 H1 118(3) . . ?
C2 C1 H1 120(3) . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 123(3) . . ?
C1 C2 H2 117(3) . . ?
C2 C3 C4 119.8(4) . . ?
C2 C3 H3 121(4) . . ?
C4 C3 H3 119(4) . . ?
C3 C4 C5 117.0(4) . . ?
C3 C4 C6 125.0(4) . . ?
C5 C4 C6 118.0(4) . . ?
N1 C5 C4 122.7(4) . . ?
N1 C5 C9 116.8(4) . . ?
C4 C5 C9 120.5(4) . . ?
C7 C6 C4 121.1(4) . . ?
C7 C6 H6 126(3) . . ?
C4 C6 H6 113(3) . . ?
C6 C7 C8 121.9(4) . . ?
C6 C7 H7 122(4) . . ?
C8 C7 H7 116(4) . . ?
C10 C8 C9 117.0(4) . . ?
C10 C8 C7 125.1(4) . . ?
C9 C8 C7 117.9(4) . . ?
N2 C9 C8 123.1(4) . . ?
N2 C9 C5 116.3(4) . . ?
C8 C9 C5 120.6(4) . . ?
C11 C10 C8 119.6(4) . . ?
C11 C10 H10 118(3) . . ?
C8 C10 H10 123(3) . . ?
C10 C11 C12 119.6(4) . . ?
C10 C11 H11 121(3) . . ?
C12 C11 H11 120(3) . . ?
N2 C12 C11 122.1(4) . . ?
N2 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
O1 C13 C14 119.3(4) . . ?
O1 C13 C18 123.3(4) . . ?
C14 C13 C18 117.4(4) . . ?
C15 C14 C13 121.4(4) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 121.2(4) . . ?
C14 C15 H15 121(3) . . ?
C16 C15 H15 117(3) . . ?
C17 C16 C15 119.1(4) . . ?
C17 C16 H16 120(3) . . ?
C15 C16 H16 121(3) . . ?
C16 C17 C18 121.4(4) . . ?
C16 C17 H17 124(3) . . ?
C18 C17 H17 114(3) . . ?
C17 C18 C19 117.9(4) . . ?
C17 C18 C13 119.5(4) . . ?
C19 C18 C13 122.6(4) . . ?
O2 C19 C18 127.6(4) . . ?
O2 C19 H18 119(3) . . ?
C18 C19 H18 114(3) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.114
_database_code_depnum_ccdc_archive 'CCDC 850172'
