# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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#  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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data_Cu-R-1
_database_code_depnum_ccdc_archive 'CCDC 904349'
#TrackingRef 'web_deposit_cif_file_0_Xi-LiLi_1355234529.904349.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 Cl2 Cu N3, 2(H2 O)'
_chemical_formula_sum            'C16 H21 Cl2 Cu N3 O2'
_chemical_formula_weight         421.80
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           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   6.3272(7)
_cell_length_b                   9.8159(12)
_cell_length_c                   16.2332(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.078(8)
_cell_angle_gamma                90.00
_cell_volume                     1002.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2267
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      25.52
_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             434
_exptl_absorpt_coefficient_mu    1.368
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7175
_exptl_absorpt_correction_T_max  0.8211
_exptl_absorpt_process_details   'SADABS; bruker, 2000'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      298(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 Aepex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3787
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0682
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2558
_reflns_number_gt                2162
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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^)+(0.1172P)^2^+3.4714P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2558
_refine_ls_number_parameters     228
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.2143
_refine_ls_wR_factor_gt          0.2029
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.102
_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 0.79377(18) 1.05209(15) 0.40155(7) 0.0294(4) Uani 1 1 d . . .
Cl1 Cl 1.0807(4) 1.0540(5) 0.49662(17) 0.0427(7) Uani 1 1 d . . .
Cl2 Cl 0.9429(5) 1.1893(4) 0.31246(19) 0.0462(9) Uani 1 1 d . . .
O1 O 0.3729(13) 0.4853(10) 0.2503(5) 0.046(2) Uani 1 1 d U . .
H1A H 0.3212 0.4411 0.2885 0.069 Uiso 1 1 d R . .
H1B H 0.4681 0.4376 0.2308 0.069 Uiso 1 1 d R . .
O2 O 0.722(3) 0.6557(19) 0.2595(11) 0.014(5) Uani 0.50 1 d PU A 1
H2A H 0.7176 0.6903 0.3072 0.020 Uiso 0.50 1 d PR A 1
H2B H 0.7945 0.7071 0.2309 0.020 Uiso 0.50 1 d PR A 1
O2' O 0.769(3) 0.6413(19) 0.2689(11) 0.013(5) Uani 0.50 1 d PU B 2
H2C H 0.7571 0.6024 0.3149 0.020 Uiso 0.50 1 d PR B 2
H2D H 0.8031 0.5827 0.2341 0.020 Uiso 0.50 1 d PR B 2
N1 N 0.4055(16) 0.7118(12) 0.5392(7) 0.032(3) Uani 1 1 d . . .
N2 N 0.6466(14) 0.9024(11) 0.4643(6) 0.023(2) Uani 1 1 d . . .
N3 N 0.5582(13) 0.9947(11) 0.3145(5) 0.029(2) Uani 1 1 d . . .
C1 C 0.703(2) 0.8581(14) 0.5398(9) 0.033(3) Uani 1 1 d . . .
H1 H 0.8264 0.8913 0.5691 0.040 Uiso 1 1 calc R . .
C2 C 0.581(2) 0.7625(17) 0.5764(9) 0.040(3) Uani 1 1 d . . .
H2 H 0.6269 0.7332 0.6298 0.048 Uiso 1 1 calc R . .
C3 C 0.3488(18) 0.7601(15) 0.4609(8) 0.031(3) Uani 1 1 d . . .
H3 H 0.2234 0.7281 0.4324 0.037 Uiso 1 1 calc R . .
C4 C 0.4640(16) 0.8512(13) 0.4230(7) 0.023(3) Uani 1 1 d . . .
C5 C 0.4153(18) 0.9018(13) 0.3395(6) 0.030(3) Uani 1 1 d . . .
C6 C 0.2402(18) 0.8594(14) 0.2892(7) 0.036(3) Uani 1 1 d . . .
H6 H 0.1467 0.7974 0.3090 0.043 Uiso 1 1 calc R . .
C7 C 0.2014(18) 0.9083(14) 0.2088(7) 0.036(3) Uani 1 1 d . . .
C8 C 0.3503(16) 1.0055(13) 0.1825(7) 0.035(3) Uani 1 1 d . . .
C9 C 0.5207(17) 1.0452(18) 0.2372(6) 0.037(3) Uani 1 1 d . . .
H9 H 0.6141 1.1098 0.2199 0.045 Uiso 1 1 calc R . .
C10 C 0.0201(19) 0.8681(17) 0.1471(8) 0.047(3) Uani 1 1 d . . .
H10A H -0.1128 0.8896 0.1689 0.056 Uiso 1 1 calc R . .
H10B H 0.0243 0.7705 0.1380 0.056 Uiso 1 1 calc R . .
C11 C 0.029(2) 0.942(2) 0.0647(8) 0.059(5) Uani 1 1 d . . .
H11 H -0.0884 0.9208 0.0221 0.071 Uiso 1 1 calc R . .
C12 C 0.071(3) 1.0951(17) 0.0803(11) 0.069(5) Uani 1 1 d . . .
H12A H 0.0110 1.1311 0.1284 0.083 Uiso 1 1 calc R . .
H12B H 0.0363 1.1524 0.0320 0.083 Uiso 1 1 calc R . .
C13 C 0.314(2) 1.055(2) 0.0966(7) 0.054(4) Uani 1 1 d . . .
H13 H 0.4160 1.1212 0.0796 0.064 Uiso 1 1 calc R . .
C14 C 0.2543(19) 0.9348(17) 0.0351(8) 0.046(3) Uani 1 1 d . . .
C15 C 0.387(3) 0.804(2) 0.0515(9) 0.071(5) Uani 1 1 d . . .
H15A H 0.5288 0.8197 0.0373 0.107 Uiso 1 1 calc R . .
H15B H 0.3231 0.7313 0.0183 0.107 Uiso 1 1 calc R . .
H15C H 0.3926 0.7805 0.1090 0.107 Uiso 1 1 calc R . .
C16 C 0.265(3) 0.973(2) -0.0545(9) 0.085(7) Uani 1 1 d . . .
H16A H 0.1793 1.0528 -0.0674 0.128 Uiso 1 1 calc R . .
H16B H 0.2121 0.8993 -0.0895 0.128 Uiso 1 1 calc R . .
H16C H 0.4094 0.9923 -0.0634 0.128 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 0.0307(6) 0.0292(7) 0.0287(6) -0.0005(8) 0.0058(4) -0.0048(8)
Cl1 0.0290(12) 0.0494(17) 0.0488(15) 0.013(2) -0.0011(10) -0.010(2)
Cl2 0.0466(17) 0.054(2) 0.0391(15) 0.0067(17) 0.0074(13) -0.0169(16)
O1 0.043(3) 0.048(3) 0.046(3) 0.0063(19) 0.0006(18) -0.0071(19)
O2 0.013(5) 0.013(5) 0.015(5) 0.004(2) 0.002(2) -0.002(2)
O2' 0.012(5) 0.013(5) 0.014(5) 0.005(2) 0.001(2) -0.004(2)
N1 0.034(5) 0.027(6) 0.037(5) 0.005(5) 0.010(4) 0.006(5)
N2 0.027(5) 0.022(6) 0.020(4) 0.000(4) 0.003(4) 0.000(4)
N3 0.033(5) 0.032(5) 0.024(4) 0.005(4) 0.004(4) -0.008(4)
C1 0.037(6) 0.026(7) 0.037(7) 0.007(6) 0.004(5) -0.002(6)
C2 0.043(7) 0.042(9) 0.037(7) 0.003(7) 0.007(6) 0.000(7)
C3 0.023(6) 0.042(8) 0.027(6) 0.003(6) 0.000(5) 0.001(6)
C4 0.023(6) 0.023(7) 0.025(6) -0.001(5) 0.006(5) 0.010(5)
C5 0.044(6) 0.028(7) 0.019(5) -0.001(5) 0.003(4) 0.000(6)
C6 0.033(6) 0.034(7) 0.040(6) 0.001(6) 0.004(5) -0.006(5)
C7 0.043(6) 0.040(8) 0.025(5) 0.001(6) 0.006(5) 0.005(6)
C8 0.032(5) 0.041(8) 0.031(5) 0.009(5) -0.004(4) -0.010(5)
C9 0.058(6) 0.035(7) 0.022(4) -0.002(7) 0.017(4) -0.020(8)
C10 0.041(7) 0.062(10) 0.035(6) -0.001(7) 0.001(5) -0.006(7)
C11 0.046(8) 0.095(15) 0.032(7) 0.007(8) -0.016(6) -0.009(9)
C12 0.075(11) 0.071(15) 0.056(9) 0.019(9) -0.019(8) 0.011(9)
C13 0.074(8) 0.052(8) 0.035(6) 0.021(9) 0.001(5) -0.038(10)
C14 0.041(7) 0.061(10) 0.037(7) -0.004(7) 0.003(5) -0.003(7)
C15 0.096(12) 0.081(14) 0.039(8) -0.021(9) 0.019(8) -0.015(11)
C16 0.092(12) 0.128(19) 0.035(8) 0.016(10) 0.001(8) -0.040(12)
_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 N3 2.022(9) . ?
Cu1 N2 2.065(10) . ?
Cu1 Cl1 2.255(3) . ?
Cu1 Cl2 2.255(3) . ?
Cu1 N1 2.287(11) 2_656 ?
O1 H1A 0.8500 . ?
O1 H1B 0.8500 . ?
O2 H2A 0.8500 . ?
O2 H2B 0.8500 . ?
O2 H2C 1.0449 . ?
O2 H2D 0.9951 . ?
O2' H2A 0.8766 . ?
O2' H2B 0.9181 . ?
O2' H2C 0.8500 . ?
O2' H2D 0.8501 . ?
N1 C2 1.307(17) . ?
N1 C3 1.367(16) . ?
N1 Cu1 2.287(11) 2_646 ?
N2 C1 1.314(17) . ?
N2 C4 1.368(15) . ?
N3 C9 1.348(14) . ?
N3 C5 1.375(15) . ?
C1 C2 1.386(19) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.344(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.445(16) . ?
C5 C6 1.370(16) . ?
C6 C7 1.387(16) . ?
C6 H6 0.9300 . ?
C7 C8 1.436(17) . ?
C7 C10 1.494(17) . ?
C8 C9 1.378(15) . ?
C8 C13 1.472(15) . ?
C9 H9 0.9300 . ?
C10 C11 1.53(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.55(3) . ?
C11 C14 1.555(19) . ?
C11 H11 0.9800 . ?
C12 C13 1.58(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.56(2) . ?
C13 H13 0.9800 . ?
C14 C16 1.510(19) . ?
C14 C15 1.54(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
N3 Cu1 N2 79.0(4) . . ?
N3 Cu1 Cl1 163.9(3) . . ?
N2 Cu1 Cl1 92.3(3) . . ?
N3 Cu1 Cl2 92.6(3) . . ?
N2 Cu1 Cl2 169.3(3) . . ?
Cl1 Cu1 Cl2 94.17(12) . . ?
N3 Cu1 N1 95.0(4) . 2_656 ?
N2 Cu1 N1 89.0(3) . 2_656 ?
Cl1 Cu1 N1 98.4(3) . 2_656 ?
Cl2 Cu1 N1 98.5(3) . 2_656 ?
H1A O1 H1B 109.5 . . ?
H2A O2 H2B 109.5 . . ?
H2A O2 H2C 55.8 . . ?
H2B O2 H2C 133.7 . . ?
H2A O2 H2D 137.3 . . ?
H2B O2 H2D 82.6 . . ?
H2C O2 H2D 85.7 . . ?
H2A O2' H2B 101.3 . . ?
H2A O2' H2C 63.1 . . ?
H2B O2' H2C 161.0 . . ?
H2A O2' H2D 169.3 . . ?
H2B O2' H2D 87.4 . . ?
H2C O2' H2D 109.5 . . ?
C2 N1 C3 115.1(12) . . ?
C2 N1 Cu1 123.1(10) . 2_646 ?
C3 N1 Cu1 121.7(9) . 2_646 ?
C1 N2 C4 117.8(11) . . ?
C1 N2 Cu1 127.1(9) . . ?
C4 N2 Cu1 114.9(8) . . ?
C9 N3 C5 117.6(10) . . ?
C9 N3 Cu1 126.3(8) . . ?
C5 N3 Cu1 116.0(7) . . ?
N2 C1 C2 121.1(13) . . ?
N2 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
N1 C2 C1 122.9(14) . . ?
N1 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C4 C3 N1 123.7(11) . . ?
C4 C3 H3 118.2 . . ?
N1 C3 H3 118.2 . . ?
C3 C4 N2 119.4(11) . . ?
C3 C4 C5 125.9(11) . . ?
N2 C4 C5 114.7(11) . . ?
C6 C5 N3 122.7(10) . . ?
C6 C5 C4 122.3(11) . . ?
N3 C5 C4 115.0(10) . . ?
C5 C6 C7 120.5(12) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 116.9(11) . . ?
C6 C7 C10 125.9(12) . . ?
C8 C7 C10 117.2(10) . . ?
C9 C8 C7 119.3(10) . . ?
C9 C8 C13 123.5(11) . . ?
C7 C8 C13 117.2(10) . . ?
N3 C9 C8 123.0(11) . . ?
N3 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
C7 C10 C11 111.5(12) . . ?
C7 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C7 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 109.8(14) . . ?
C10 C11 C14 111.7(12) . . ?
C12 C11 C14 86.9(13) . . ?
C10 C11 H11 115.1 . . ?
C12 C11 H11 115.1 . . ?
C14 C11 H11 115.1 . . ?
C11 C12 C13 86.0(12) . . ?
C11 C12 H12A 114.3 . . ?
C13 C12 H12A 114.3 . . ?
C11 C12 H12B 114.3 . . ?
C13 C12 H12B 114.3 . . ?
H12A C12 H12B 111.5 . . ?
C8 C13 C14 111.3(13) . . ?
C8 C13 C12 107.0(11) . . ?
C14 C13 C12 85.3(10) . . ?
C8 C13 H13 116.3 . . ?
C14 C13 H13 116.3 . . ?
C12 C13 H13 116.3 . . ?
C16 C14 C15 107.2(14) . . ?
C16 C14 C11 114.9(12) . . ?
C15 C14 C11 119.0(14) . . ?
C16 C14 C13 113.3(14) . . ?
C15 C14 C13 115.2(11) . . ?
C11 C14 C13 86.4(11) . . ?
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        25.10
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.653
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.147


data_Cu-S-1
_database_code_depnum_ccdc_archive 'CCDC 904350'
#TrackingRef 'web_deposit_cif_file_1_Xi-LiLi_1355234529.904350.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 Cl2 Cu N3, 2(H2 O)'
_chemical_formula_sum            'C16 H21 Cl2 Cu N3 O2'
_chemical_formula_weight         421.80
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'
Cl Cl 0.1484 0.1585 '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 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   6.3364(7)
_cell_length_b                   9.8456(9)
_cell_length_c                   16.314(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.190(10)
_cell_angle_gamma                90.00
_cell_volume                     1011.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1968
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      27.32
_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             434
_exptl_absorpt_coefficient_mu    1.355
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7457
_exptl_absorpt_correction_T_max  0.8543
_exptl_absorpt_process_details   'SADABS; bruker, 2000'
_diffrn_ambient_temperature      298(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 Aepex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3745
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.84
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2890
_reflns_number_gt                2517
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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^)+(0.0971P)^2^+0.3153P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2890
_refine_ls_number_parameters     228
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1590
_refine_ls_wR_factor_gt          0.1513
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
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 1.29394(12) 0.30702(9) 0.40147(5) 0.0292(3) Uani 1 1 d . . .
Cl1 Cl 1.5807(2) 0.3044(3) 0.49635(12) 0.0430(5) Uani 1 1 d . . .
Cl2 Cl 1.4427(3) 0.1699(2) 0.31236(14) 0.0462(6) Uani 1 1 d . . .
O1 O 0.8720(10) 0.8742(7) 0.2506(4) 0.0520(16) Uani 1 1 d U . .
H1A H 0.9188 0.8464 0.2067 0.078 Uiso 1 1 d R . .
H1B H 0.9149 0.9548 0.2608 0.078 Uiso 1 1 d R . .
O2 O 0.2319(16) 0.7092(11) 0.2582(7) 0.016(3) Uani 0.60 1 d PU A 1
H2A H 0.1970 0.7561 0.2983 0.024 Uiso 0.60 1 d PR A 1
H2B H 0.1340 0.6527 0.2432 0.024 Uiso 0.60 1 d PR A 1
O2' O 0.274(3) 0.712(2) 0.2753(11) 0.026(5) Uani 0.40 1 d PU B 2
H2C H 0.3339 0.6543 0.2466 0.038 Uiso 0.40 1 d PR B 2
H2D H 0.2755 0.7895 0.2527 0.038 Uiso 0.40 1 d PR B 2
N1 N 0.9033(10) 0.6456(7) 0.5387(5) 0.0310(16) Uani 1 1 d . . .
N2 N 1.1451(10) 0.4550(7) 0.4648(4) 0.0267(15) Uani 1 1 d . . .
N3 N 1.0555(10) 0.3630(7) 0.3144(4) 0.0317(14) Uani 1 1 d . . .
C1 C 1.2043(14) 0.5002(9) 0.5414(7) 0.037(2) Uani 1 1 d . . .
H1 H 1.3291 0.4688 0.5705 0.045 Uiso 1 1 calc R . .
C2 C 1.0794(14) 0.5935(10) 0.5770(7) 0.036(2) Uani 1 1 d . . .
H2 H 1.1214 0.6211 0.6308 0.043 Uiso 1 1 calc R . .
C3 C 0.8464(13) 0.5986(10) 0.4611(6) 0.034(2) Uani 1 1 d . . .
H3 H 0.7215 0.6305 0.4324 0.041 Uiso 1 1 calc R . .
C4 C 0.9656(13) 0.5063(9) 0.4236(6) 0.0289(19) Uani 1 1 d . . .
C5 C 0.9112(12) 0.4553(8) 0.3389(5) 0.0314(17) Uani 1 1 d . . .
C6 C 0.7405(12) 0.4995(9) 0.2895(5) 0.0349(18) Uani 1 1 d . . .
H6 H 0.6493 0.5634 0.3085 0.042 Uiso 1 1 calc R . .
C7 C 0.7021(12) 0.4471(9) 0.2086(5) 0.0352(18) Uani 1 1 d . . .
C8 C 0.8513(12) 0.3547(9) 0.1836(5) 0.0358(19) Uani 1 1 d . . .
C9 C 1.0198(12) 0.3162(11) 0.2381(4) 0.0369(17) Uani 1 1 d . . .
H9 H 1.1149 0.2534 0.2206 0.044 Uiso 1 1 calc R . .
C10 C 0.5221(13) 0.4904(12) 0.1471(6) 0.049(2) Uani 1 1 d . . .
H10A H 0.5306 0.5875 0.1377 0.059 Uiso 1 1 calc R . .
H10B H 0.3883 0.4717 0.1687 0.059 Uiso 1 1 calc R . .
C11 C 0.5300(15) 0.4159(12) 0.0667(6) 0.056(3) Uani 1 1 d . . .
H11 H 0.4126 0.4364 0.0244 0.067 Uiso 1 1 calc R . .
C12 C 0.5744(19) 0.2635(12) 0.0806(9) 0.072(4) Uani 1 1 d . . .
H12A H 0.5400 0.2075 0.0321 0.087 Uiso 1 1 calc R . .
H12B H 0.5162 0.2258 0.1283 0.087 Uiso 1 1 calc R . .
C13 C 0.8098(14) 0.3045(13) 0.0963(5) 0.054(2) Uani 1 1 d . . .
H13 H 0.9121 0.2387 0.0789 0.065 Uiso 1 1 calc R . .
C14 C 0.7552(14) 0.4259(12) 0.0370(6) 0.055(3) Uani 1 1 d . . .
C15 C 0.8857(17) 0.5573(13) 0.0528(7) 0.064(3) Uani 1 1 d . . .
H15A H 0.9116 0.5731 0.1111 0.096 Uiso 1 1 calc R . .
H15B H 0.8081 0.6324 0.0270 0.096 Uiso 1 1 calc R . .
H15C H 1.0186 0.5480 0.0302 0.096 Uiso 1 1 calc R . .
C16 C 0.761(2) 0.3816(17) -0.0545(7) 0.094(5) Uani 1 1 d . . .
H16A H 0.9054 0.3638 -0.0644 0.141 Uiso 1 1 calc R . .
H16B H 0.7043 0.4529 -0.0905 0.141 Uiso 1 1 calc R . .
H16C H 0.6780 0.3008 -0.0651 0.141 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 0.0299(4) 0.0285(4) 0.0296(5) 0.0003(6) 0.0053(3) 0.0041(5)
Cl1 0.0305(8) 0.0482(10) 0.0489(11) -0.0125(15) -0.0017(7) 0.0091(13)
Cl2 0.0449(11) 0.0538(14) 0.0400(12) -0.0061(11) 0.0052(9) 0.0179(10)
O1 0.048(2) 0.055(2) 0.052(2) -0.0110(18) -0.0024(17) 0.0106(18)
O2 0.016(3) 0.015(3) 0.016(3) -0.0076(19) 0.0001(19) 0.0053(18)
O2' 0.025(5) 0.025(5) 0.026(5) -0.005(2) 0.001(2) 0.007(2)
N1 0.031(4) 0.029(4) 0.034(4) -0.004(3) 0.008(3) -0.005(3)
N2 0.028(3) 0.027(4) 0.025(4) 0.007(3) 0.003(3) 0.003(3)
N3 0.037(3) 0.030(3) 0.029(4) -0.003(3) 0.005(3) 0.008(3)
C1 0.037(5) 0.023(4) 0.053(6) 0.003(4) 0.009(4) 0.003(4)
C2 0.038(5) 0.033(5) 0.036(5) -0.008(5) 0.003(4) 0.001(4)
C3 0.026(4) 0.049(5) 0.025(4) -0.015(4) -0.005(3) -0.001(4)
C4 0.032(4) 0.026(4) 0.030(5) -0.007(4) 0.007(4) -0.005(4)
C5 0.034(4) 0.034(4) 0.026(4) 0.000(4) 0.000(3) -0.001(4)
C6 0.031(4) 0.039(4) 0.035(5) 0.003(4) 0.007(3) 0.012(4)
C7 0.038(4) 0.041(5) 0.025(4) 0.002(4) -0.002(3) -0.006(4)
C8 0.042(4) 0.041(5) 0.022(4) -0.006(4) -0.005(3) 0.010(4)
C9 0.055(4) 0.028(4) 0.029(4) -0.001(5) 0.011(3) 0.014(5)
C10 0.031(4) 0.076(7) 0.038(5) 0.003(5) -0.005(4) 0.006(5)
C11 0.040(5) 0.081(8) 0.042(6) -0.013(6) -0.012(4) 0.006(5)
C12 0.069(7) 0.079(9) 0.066(7) -0.021(7) -0.010(5) -0.022(6)
C13 0.068(5) 0.056(5) 0.038(4) -0.019(7) -0.003(4) 0.037(7)
C14 0.047(5) 0.083(7) 0.034(5) 0.005(5) -0.001(4) 0.020(5)
C15 0.069(7) 0.079(8) 0.046(6) 0.020(6) 0.011(5) -0.008(6)
C16 0.116(10) 0.132(12) 0.032(6) -0.002(7) -0.007(6) 0.044(9)
_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 N3 2.035(7) . ?
Cu1 N2 2.072(7) . ?
Cu1 Cl1 2.2562(19) . ?
Cu1 Cl2 2.263(2) . ?
Cu1 N1 2.303(7) 2_746 ?
O1 H1A 0.8500 . ?
O1 H1B 0.8499 . ?
O2 H2A 0.8500 . ?
O2 H2B 0.8500 . ?
O2 H2C 0.8785 . ?
O2 H2D 0.8450 . ?
O2' H2A 0.7797 . ?
O2' H2B 1.1385 . ?
O2' H2C 0.8500 . ?
O2' H2D 0.8500 . ?
N1 C2 1.323(11) . ?
N1 C3 1.360(11) . ?
N1 Cu1 2.303(7) 2_756 ?
N2 C1 1.341(13) . ?
N2 C4 1.355(11) . ?
N3 C9 1.323(10) . ?
N3 C5 1.379(10) . ?
C1 C2 1.380(13) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.368(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.476(12) . ?
C5 C6 1.349(11) . ?
C6 C7 1.414(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.404(12) . ?
C7 C10 1.497(12) . ?
C8 C9 1.368(10) . ?
C8 C13 1.504(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.508(14) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.538(18) . ?
C11 C14 1.559(13) . ?
C11 H11 0.9800 . ?
C12 C13 1.540(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.553(15) . ?
C13 H13 0.9800 . ?
C14 C15 1.542(16) . ?
C14 C16 1.561(15) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
N3 Cu1 N2 79.3(3) . . ?
N3 Cu1 Cl1 164.6(2) . . ?
N2 Cu1 Cl1 92.4(2) . . ?
N3 Cu1 Cl2 92.42(18) . . ?
N2 Cu1 Cl2 169.7(2) . . ?
Cl1 Cu1 Cl2 94.23(8) . . ?
N3 Cu1 N1 95.0(3) . 2_746 ?
N2 Cu1 N1 88.7(2) . 2_746 ?
Cl1 Cu1 N1 97.76(19) . 2_746 ?
Cl2 Cu1 N1 98.24(19) . 2_746 ?
H1A O1 H1B 109.5 . . ?
H2A O2 H2B 109.5 . . ?
H2A O2 H2C 139.3 . . ?
H2B O2 H2C 93.8 . . ?
H2A O2 H2D 71.9 . . ?
H2B O2 H2D 145.1 . . ?
H2C O2 H2D 107.3 . . ?
H2A O2' H2B 90.7 . . ?
H2A O2' H2C 168.0 . . ?
H2B O2' H2C 77.3 . . ?
H2A O2' H2D 75.1 . . ?
H2B O2' H2D 107.9 . . ?
H2C O2' H2D 109.5 . . ?
C2 N1 C3 115.7(8) . . ?
C2 N1 Cu1 122.5(6) . 2_756 ?
C3 N1 Cu1 121.9(6) . 2_756 ?
C1 N2 C4 118.3(7) . . ?
C1 N2 Cu1 127.0(6) . . ?
C4 N2 Cu1 114.6(6) . . ?
C9 N3 C5 116.8(7) . . ?
C9 N3 Cu1 126.9(5) . . ?
C5 N3 Cu1 116.2(5) . . ?
N2 C1 C2 119.8(9) . . ?
N2 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
N1 C2 C1 123.5(10) . . ?
N1 C2 H2 118.2 . . ?
C1 C2 H2 118.2 . . ?
N1 C3 C4 122.6(8) . . ?
N1 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
N2 C4 C3 120.0(9) . . ?
N2 C4 C5 115.9(7) . . ?
C3 C4 C5 124.1(8) . . ?
C6 C5 N3 123.6(8) . . ?
C6 C5 C4 122.7(8) . . ?
N3 C5 C4 113.6(7) . . ?
C5 C6 C7 119.1(8) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 117.0(7) . . ?
C8 C7 C10 118.6(8) . . ?
C6 C7 C10 124.3(8) . . ?
C9 C8 C7 119.6(7) . . ?
C9 C8 C13 124.7(7) . . ?
C7 C8 C13 115.7(7) . . ?
N3 C9 C8 123.9(8) . . ?
N3 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C7 C10 C11 110.5(8) . . ?
C7 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C7 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 111.7(10) . . ?
C10 C11 C14 110.9(8) . . ?
C12 C11 C14 87.1(9) . . ?
C10 C11 H11 114.7 . . ?
C12 C11 H11 114.7 . . ?
C14 C11 H11 114.7 . . ?
C11 C12 C13 85.8(8) . . ?
C11 C12 H12A 114.3 . . ?
C13 C12 H12A 114.3 . . ?
C11 C12 H12B 114.3 . . ?
C13 C12 H12B 114.3 . . ?
H12A C12 H12B 111.5 . . ?
C8 C13 C12 108.1(8) . . ?
C8 C13 C14 109.9(9) . . ?
C12 C13 C14 87.2(8) . . ?
C8 C13 H13 116.0 . . ?
C12 C13 H13 116.0 . . ?
C14 C13 H13 116.0 . . ?
C15 C14 C13 117.5(8) . . ?
C15 C14 C11 119.6(9) . . ?
C13 C14 C11 84.7(8) . . ?
C15 C14 C16 109.1(10) . . ?
C13 C14 C16 110.7(10) . . ?
C11 C14 C16 113.4(9) . . ?
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 0.981
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         1.103
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.104