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


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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_data
_database_code_depnum_ccdc_archive 'CCDC 905445'
#TrackingRef '14599_web_deposit_cif_file_0_KaylaGreen_1349890122.101012.cif'

_audit_creation_date             2012-09-06
_audit_creation_method           
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C11 H18 Cl2 Cu N4 O5'
_chemical_formula_sum            'C11 H18 Cl2 Cu N4 O5'
_chemical_formula_weight         423.76
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            'clear blue'
_diffrn_ambient_temperature      220
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           p_1_21/c_1
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.454(5)
_cell_length_b                   8.985(4)
_cell_length_c                   18.166(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.113(19)
_cell_angle_gamma                90.00
_cell_volume                     1583.5(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8766
_cell_measurement_temperature    220
_cell_measurement_theta_max      27.668
_cell_measurement_theta_min      2.346
_exptl_absorpt_coefficient_mu    1.747
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.0649 before and 0.0290 after correction.
The Ratio of minimum to maximum transmission is 0.8310.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
The data collection nominally covered a full sphere of reciprocal space by
a combination of 4 sets of \w scans each set at different \f and/or
2\q angles and each scan (10 s exposure) covering -0.300\% degrees in \w.
The crystal to detector distance was 5.0 cm.
;
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13671
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         2.10
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Smart 100'
_diffrn_measurement_method       multi-scan
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          ?
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              NLCS
_diffrn_source_current           40.0
_diffrn_source_power             1.6
_diffrn_source_target            MO
_diffrn_source_voltage           40.0
_reflns_number_gt                3283
_reflns_number_total             3617
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     292
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0245
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0325P)^2^+1.0702P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0660
_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.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.63176(2) 0.18741(2) 0.147745(14) 0.02223(8) Uani 1 1 d . . .
Cl1 Cl 0.51318(5) -0.01374(5) 0.14134(4) 0.03643(13) Uani 1 1 d . . .
O9 O 0.7259(2) 0.77553(17) 0.03032(12) 0.0518(5) Uani 1 1 d . . .
H9 H 0.7682 0.7654 0.0058 0.078 Uiso 1 1 d R . .
N1 N 0.83548(16) 0.16702(18) 0.26471(11) 0.0285(3) Uani 1 1 d . . .
H1 H 0.8500 0.0865 0.2980 0.034 Uiso 1 1 d R . .
N2 N 0.59229(16) 0.32766(17) 0.22329(10) 0.0259(3) Uani 1 1 d . . .
H2 H 0.5162 0.2971 0.2217 0.031 Uiso 1 1 d R . .
N3 N 0.65610(14) 0.37596(16) 0.10562(9) 0.0211(3) Uani 1 1 d . . .
N4 N 0.72688(15) 0.10770(17) 0.08492(10) 0.0249(3) Uani 1 1 d . . .
H4 H 0.6778 0.0314 0.0499 0.030 Uiso 1 1 d R . .
C1 C 0.8462(2) 0.2991(2) 0.31537(13) 0.0326(4) Uani 1 1 d . . .
H1A H 0.8606 0.3881 0.2900 0.039 Uiso 1 1 calc R . .
H1B H 0.9244 0.2889 0.3754 0.039 Uiso 1 1 calc R . .
C2 C 0.7125(2) 0.3129(2) 0.31383(13) 0.0339(4) Uani 1 1 d . . .
H2A H 0.7006 0.2247 0.3409 0.041 Uiso 1 1 calc R . .
H2B H 0.7174 0.4003 0.3477 0.041 Uiso 1 1 calc R . .
C3 C 0.5695(2) 0.4816(2) 0.18892(13) 0.0277(4) Uani 1 1 d . . .
H3A H 0.6128 0.5521 0.2375 0.033 Uiso 1 1 calc R . .
H3B H 0.4704 0.5025 0.1546 0.033 Uiso 1 1 calc R . .
C4 C 0.62937(17) 0.5031(2) 0.13260(11) 0.0225(3) Uani 1 1 d . . .
C5 C 0.71283(17) 0.37774(19) 0.05696(11) 0.0210(3) Uani 1 1 d . . .
C6 C 0.7359(2) 0.2266(2) 0.03142(12) 0.0261(4) Uani 1 1 d . . .
H6A H 0.6666 0.2086 -0.0300 0.031 Uiso 1 1 calc R . .
H6B H 0.8270 0.2237 0.0387 0.031 Uiso 1 1 calc R . .
C7 C 0.8633(2) 0.0516(2) 0.15469(14) 0.0333(4) Uani 1 1 d . . .
H7A H 0.9240 0.0417 0.1322 0.040 Uiso 1 1 calc R . .
H7B H 0.8525 -0.0471 0.1733 0.040 Uiso 1 1 calc R . .
C8 C 0.9286(2) 0.1568(2) 0.23208(14) 0.0330(4) Uani 1 1 d . . .
H8A H 1.0187 0.1187 0.2777 0.040 Uiso 1 1 calc R . .
H8B H 0.9416 0.2553 0.2144 0.040 Uiso 1 1 calc R . .
C9 C 0.7416(2) 0.5092(2) 0.03111(12) 0.0260(4) Uani 1 1 d . . .
H9A H 0.7832 0.5099 -0.0017 0.031 Uiso 1 1 calc R . .
C10 C 0.7070(2) 0.6418(2) 0.05506(12) 0.0295(4) Uani 1 1 d . . .
C11 C 0.6528(2) 0.6386(2) 0.10837(12) 0.0277(4) Uani 1 1 d . . .
H11 H 0.6330 0.7274 0.1270 0.033 Uiso 1 1 calc R . .
Cl3 Cl 0.14880(5) 0.28333(6) 0.11709(3) 0.03221(12) Uani 1 1 d D . .
O1 O 0.0952(9) 0.2310(12) 0.0339(4) 0.066(3) Uani 0.364(12) 1 d PDU A 1
O2 O 0.2812(9) 0.3437(18) 0.1478(7) 0.075(4) Uani 0.364(12) 1 d PDU A 1
O3 O 0.0643(11) 0.3946(12) 0.1226(8) 0.076(5) Uani 0.364(12) 1 d PDU A 1
O4 O 0.1579(16) 0.1679(14) 0.1737(8) 0.091(5) Uani 0.364(12) 1 d PDU A 1
O1' O 0.038(3) 0.300(4) 0.0313(11) 0.048(9) Uani 0.078(10) 1 d PDU A 2
O2' O 0.262(3) 0.382(4) 0.1412(16) 0.040(9) Uani 0.078(10) 1 d PDU A 2
O3' O 0.043(3) 0.377(3) 0.1156(15) 0.027(7) Uani 0.078(10) 1 d PDU A 2
O4' O 0.187(3) 0.176(2) 0.1808(11) 0.034(8) Uani 0.078(10) 1 d PDU A 2
O1" O 0.0544(6) 0.1884(8) 0.0461(4) 0.089(2) Uani 0.560(9) 1 d PDU A 3
O2" O 0.2792(4) 0.2615(6) 0.1235(3) 0.0485(12) Uani 0.560(9) 1 d PDU A 3
O3" O 0.1134(9) 0.4330(6) 0.0960(4) 0.116(3) Uani 0.560(9) 1 d PDU A 3
O4" O 0.1571(7) 0.2450(9) 0.1931(3) 0.0721(19) Uani 0.560(9) 1 d PDU A 3

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 0.02260(12) 0.02189(12) 0.02663(13) -0.00268(8) 0.01607(10) -0.00442(8)
Cl1 0.0408(3) 0.0295(2) 0.0505(3) -0.0084(2) 0.0319(2) -0.0140(2)
O9 0.1032(15) 0.0227(7) 0.0595(11) 0.0020(7) 0.0636(11) -0.0025(8)
N1 0.0273(8) 0.0312(8) 0.0286(8) 0.0033(6) 0.0161(7) 0.0007(6)
N2 0.0256(7) 0.0312(8) 0.0290(8) -0.0016(6) 0.0199(7) -0.0035(6)
N3 0.0215(7) 0.0227(7) 0.0212(7) -0.0019(6) 0.0128(6) -0.0011(6)
N4 0.0270(7) 0.0204(7) 0.0302(8) -0.0052(6) 0.0172(7) -0.0038(6)
C1 0.0282(9) 0.0430(11) 0.0225(9) -0.0037(8) 0.0107(8) -0.0013(8)
C2 0.0383(11) 0.0438(12) 0.0255(10) -0.0001(8) 0.0209(9) 0.0013(9)
C3 0.0295(9) 0.0295(9) 0.0326(10) -0.0023(7) 0.0221(8) 0.0017(7)
C4 0.0197(8) 0.0263(9) 0.0210(8) -0.0023(6) 0.0104(7) 0.0017(6)
C5 0.0202(7) 0.0247(8) 0.0180(8) -0.0021(6) 0.0101(6) -0.0011(6)
C6 0.0323(9) 0.0252(9) 0.0291(9) -0.0044(7) 0.0218(8) -0.0027(7)
C7 0.0334(10) 0.0302(10) 0.0402(11) 0.0017(8) 0.0222(9) 0.0082(8)
C8 0.0234(9) 0.0425(11) 0.0330(10) 0.0019(8) 0.0148(8) 0.0042(8)
C9 0.0334(9) 0.0274(9) 0.0225(8) -0.0014(7) 0.0185(8) -0.0035(7)
C10 0.0418(11) 0.0233(9) 0.0254(9) 0.0015(7) 0.0193(8) -0.0016(8)
C11 0.0345(10) 0.0234(9) 0.0272(9) -0.0007(7) 0.0177(8) 0.0038(7)
Cl3 0.0272(2) 0.0428(3) 0.0275(2) 0.00124(19) 0.01514(19) 0.00186(19)
O1 0.059(5) 0.107(7) 0.036(3) -0.030(3) 0.030(3) -0.038(5)
O2 0.036(4) 0.115(9) 0.076(7) -0.002(6) 0.030(4) -0.024(5)
O3 0.049(5) 0.052(5) 0.111(8) -0.034(5) 0.031(4) 0.003(4)
O4 0.077(7) 0.092(8) 0.118(9) 0.069(7) 0.062(7) 0.016(6)
O1' 0.048(11) 0.060(12) 0.033(10) -0.006(7) 0.019(7) -0.001(7)
O2' 0.030(13) 0.070(15) 0.017(10) 0.003(9) 0.011(9) -0.028(11)
O3' 0.014(8) 0.022(9) 0.032(9) 0.001(7) 0.004(6) -0.002(6)
O4' 0.042(13) 0.028(12) 0.018(11) 0.012(8) 0.007(8) 0.006(9)
O1" 0.058(3) 0.139(6) 0.071(3) -0.057(3) 0.036(3) -0.044(3)
O2" 0.0348(16) 0.078(3) 0.043(2) 0.0044(19) 0.0274(16) 0.0024(18)
O3" 0.193(7) 0.092(4) 0.097(4) 0.043(3) 0.100(4) 0.092(4)
O4" 0.067(3) 0.127(6) 0.044(2) 0.006(3) 0.044(2) -0.016(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl1 2.2264(9) . ?
Cu1 N1 2.1730(19) . ?
Cu1 N2 2.0821(16) . ?
Cu1 N3 1.9392(16) . ?
Cu1 N4 2.0796(16) . ?
O9 H9 0.8193 . ?
O9 C10 1.340(2) . ?
N1 H1 0.9000 . ?
N1 C1 1.466(3) . ?
N1 C8 1.473(3) . ?
N2 H2 0.9001 . ?
N2 C2 1.487(3) . ?
N2 C3 1.483(2) . ?
N3 C4 1.341(2) . ?
N3 C5 1.347(2) . ?
N4 H4 0.9001 . ?
N4 C6 1.484(2) . ?
N4 C7 1.482(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 C2 1.522(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 C4 1.516(2) . ?
C4 C11 1.369(3) . ?
C5 C6 1.503(2) . ?
C5 C9 1.375(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 C8 1.520(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 H9A 0.9400 . ?
C9 C10 1.396(3) . ?
C10 C11 1.401(3) . ?
C11 H11 0.9400 . ?
Cl3 O1 1.376(5) . ?
Cl3 O2 1.416(6) . ?
Cl3 O3 1.432(6) . ?
Cl3 O4 1.425(7) . ?
Cl3 O1' 1.401(14) . ?
Cl3 O2' 1.434(12) . ?
Cl3 O3' 1.464(12) . ?
Cl3 O4' 1.390(11) . ?
Cl3 O1" 1.441(4) . ?
Cl3 O2" 1.448(3) . ?
Cl3 O3" 1.398(5) . ?
Cl3 O4" 1.376(4) . ?
O1' O3' 1.65(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
N1 Cu1 Cl1 106.91(5) . . ?
N2 Cu1 Cl1 100.69(5) . . ?
N2 Cu1 N1 84.44(7) . . ?
N3 Cu1 Cl1 154.20(5) . . ?
N3 Cu1 N1 98.89(6) . . ?
N3 Cu1 N2 81.87(6) . . ?
N3 Cu1 N4 81.79(6) . . ?
N4 Cu1 Cl1 100.07(5) . . ?
N4 Cu1 N1 84.49(7) . . ?
N4 Cu1 N2 158.57(6) . . ?
C10 O9 H9 109.3 . . ?
Cu1 N1 H1 116.3 . . ?
C1 N1 Cu1 103.52(12) . . ?
C1 N1 H1 107.8 . . ?
C1 N1 C8 117.78(16) . . ?
C8 N1 Cu1 104.04(12) . . ?
C8 N1 H1 107.8 . . ?
Cu1 N2 H2 109.9 . . ?
C2 N2 Cu1 106.09(12) . . ?
C2 N2 H2 108.7 . . ?
C3 N2 Cu1 109.77(11) . . ?
C3 N2 H2 108.7 . . ?
C3 N2 C2 113.64(15) . . ?
C4 N3 Cu1 119.42(12) . . ?
C4 N3 C5 120.88(15) . . ?
C5 N3 Cu1 119.34(12) . . ?
Cu1 N4 H4 109.7 . . ?
C6 N4 Cu1 110.53(11) . . ?
C6 N4 H4 108.7 . . ?
C7 N4 Cu1 105.64(12) . . ?
C7 N4 H4 108.9 . . ?
C7 N4 C6 113.33(15) . . ?
N1 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
N1 C1 C2 107.86(16) . . ?
H1A C1 H1B 108.4 . . ?
C2 C1 H1A 110.1 . . ?
C2 C1 H1B 110.1 . . ?
N2 C2 C1 111.02(16) . . ?
N2 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
N2 C3 C4 111.19(14) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
N3 C4 C3 114.28(15) . . ?
N3 C4 C11 121.22(16) . . ?
C11 C4 C3 124.49(16) . . ?
N3 C5 C6 114.65(15) . . ?
N3 C5 C9 121.42(16) . . ?
C9 C5 C6 123.88(15) . . ?
N4 C6 C5 111.30(14) . . ?
N4 C6 H6A 109.4 . . ?
N4 C6 H6B 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
N4 C7 C8 110.86(16) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
N1 C8 C7 107.81(16) . . ?
N1 C8 H8A 110.1 . . ?
N1 C8 H8B 110.1 . . ?
C7 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
H8A C8 H8B 108.5 . . ?
C5 C9 H9A 121.1 . . ?
C5 C9 C10 117.88(16) . . ?
C10 C9 H9A 121.1 . . ?
O9 C10 C9 122.53(17) . . ?
O9 C10 C11 117.35(18) . . ?
C9 C10 C11 120.11(17) . . ?
C4 C11 C10 118.35(17) . . ?
C4 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
O1 Cl3 O2 108.9(5) . . ?
O1 Cl3 O3 113.1(7) . . ?
O1 Cl3 O4 111.2(7) . . ?
O1 Cl3 O1' 37.3(14) . . ?
O1 Cl3 O2' 110.4(10) . . ?
O1 Cl3 O3' 107.1(10) . . ?
O1 Cl3 O4' 115.9(10) . . ?
O1 Cl3 O1" 29.7(3) . . ?
O1 Cl3 O2" 83.2(4) . . ?
O1 Cl3 O3" 97.6(5) . . ?
O2 Cl3 O3 109.1(6) . . ?
O2 Cl3 O4 110.0(7) . . ?
O2 Cl3 O2' 15.6(18) . . ?
O2 Cl3 O3' 119.4(15) . . ?
O2 Cl3 O1" 135.8(6) . . ?
O2 Cl3 O2" 34.7(6) . . ?
O3 Cl3 O2' 94.9(17) . . ?
O3 Cl3 O3' 10.3(15) . . ?
O3 Cl3 O1" 105.2(6) . . ?
O3 Cl3 O2" 142.7(5) . . ?
O4 Cl3 O3 104.5(6) . . ?
O4 Cl3 O2' 121.4(15) . . ?
O4 Cl3 O3' 100.0(15) . . ?
O4 Cl3 O1" 86.9(7) . . ?
O4 Cl3 O2" 99.6(7) . . ?
O1' Cl3 O2 123.2(15) . . ?
O1' Cl3 O3 75.7(17) . . ?
O1' Cl3 O4 123.7(16) . . ?
O1' Cl3 O2' 114.5(19) . . ?
O1' Cl3 O3' 70.3(17) . . ?
O1' Cl3 O1" 42.5(14) . . ?
O1' Cl3 O2" 113.2(15) . . ?
O2' Cl3 O3' 105.1(11) . . ?
O2' Cl3 O1" 139.9(10) . . ?
O2' Cl3 O2" 47.9(15) . . ?
O4' Cl3 O2 98.3(16) . . ?
O4' Cl3 O3 110.5(16) . . ?
O4' Cl3 O4 11.8(17) . . ?
O4' Cl3 O1' 134.3(19) . . ?
O4' Cl3 O2' 110.1(11) . . ?
O4' Cl3 O3' 107.6(10) . . ?
O4' Cl3 O1" 95.0(11) . . ?
O4' Cl3 O2" 89.3(14) . . ?
O4' Cl3 O3" 144.5(11) . . ?
O1" Cl3 O3' 95.8(12) . . ?
O1" Cl3 O2" 104.1(3) . . ?
O2" Cl3 O3' 152.7(14) . . ?
O3" Cl3 O2 80.4(7) . . ?
O3" Cl3 O3 40.4(5) . . ?
O3" Cl3 O4 142.9(6) . . ?
O3" Cl3 O1' 68.4(15) . . ?
O3" Cl3 O2' 64.9(16) . . ?
O3" Cl3 O3' 47.6(14) . . ?
O3" Cl3 O1" 110.7(4) . . ?
O3" Cl3 O2" 106.8(4) . . ?
O4" Cl3 O1 140.2(4) . . ?
O4" Cl3 O2 102.2(6) . . ?
O4" Cl3 O3 78.1(6) . . ?
O4" Cl3 O4 32.3(6) . . ?
O4" Cl3 O1' 132.8(14) . . ?
O4" Cl3 O2' 106.2(10) . . ?
O4" Cl3 O3' 77.1(11) . . ?
O4" Cl3 O4' 33.4(11) . . ?
O4" Cl3 O1" 111.6(4) . . ?
O4" Cl3 O2" 111.5(3) . . ?
O4" Cl3 O3" 111.8(4) . . ?
Cl3 O1' O3' 56.7(11) . . ?
Cl3 O3' O1' 53.1(9) . . ?

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
Cu1 N1 C1 C2 45.94(17) . . . . ?
Cu1 N1 C8 C7 -43.44(17) . . . . ?
Cu1 N2 C2 C1 38.10(19) . . . . ?
Cu1 N2 C3 C4 -20.02(18) . . . . ?
Cu1 N3 C4 C3 -5.1(2) . . . . ?
Cu1 N3 C4 C11 176.18(14) . . . . ?
Cu1 N3 C5 C6 7.1(2) . . . . ?
Cu1 N3 C5 C9 -175.07(13) . . . . ?
Cu1 N4 C6 C5 16.36(17) . . . . ?
Cu1 N4 C7 C8 -41.48(18) . . . . ?
Cl1 Cu1 N1 C1 -120.14(12) . . . . ?
Cl1 Cu1 N1 C8 116.19(12) . . . . ?
Cl1 Cu1 N2 C2 96.97(12) . . . . ?
Cl1 Cu1 N2 C3 -139.85(11) . . . . ?
Cl1 Cu1 N3 C4 92.54(16) . . . . ?
Cl1 Cu1 N3 C5 -94.21(15) . . . . ?
Cl1 Cu1 N4 C6 143.54(11) . . . . ?
Cl1 Cu1 N4 C7 -93.51(12) . . . . ?
O9 C10 C11 C4 178.33(18) . . . . ?
N1 Cu1 N2 C2 -9.23(12) . . . . ?
N1 Cu1 N2 C3 113.95(12) . . . . ?
N1 Cu1 N3 C4 -88.24(14) . . . . ?
N1 Cu1 N3 C5 85.01(13) . . . . ?
N1 Cu1 N4 C6 -110.22(12) . . . . ?
N1 Cu1 N4 C7 12.73(12) . . . . ?
N1 C1 C2 N2 -59.5(2) . . . . ?
N2 Cu1 N1 C1 -20.63(12) . . . . ?
N2 Cu1 N1 C8 -144.30(13) . . . . ?
N2 Cu1 N3 C4 -5.22(13) . . . . ?
N2 Cu1 N3 C5 168.03(14) . . . . ?
N2 Cu1 N4 C6 -51.0(2) . . . . ?
N2 Cu1 N4 C7 71.9(2) . . . . ?
N2 C3 C4 N3 17.0(2) . . . . ?
N2 C3 C4 C11 -164.33(17) . . . . ?
N3 Cu1 N1 C1 60.21(13) . . . . ?
N3 Cu1 N1 C8 -63.45(13) . . . . ?
N3 Cu1 N2 C2 -109.06(12) . . . . ?
N3 Cu1 N2 C3 14.12(12) . . . . ?
N3 Cu1 N4 C6 -10.39(11) . . . . ?
N3 Cu1 N4 C7 112.56(12) . . . . ?
N3 C4 C11 C10 -0.6(3) . . . . ?
N3 C5 C6 N4 -15.6(2) . . . . ?
N3 C5 C9 C10 -1.6(3) . . . . ?
N4 Cu1 N1 C1 140.99(12) . . . . ?
N4 Cu1 N1 C8 17.32(12) . . . . ?
N4 Cu1 N2 C2 -68.4(2) . . . . ?
N4 Cu1 N2 C3 54.7(2) . . . . ?
N4 Cu1 N3 C4 -171.31(14) . . . . ?
N4 Cu1 N3 C5 1.94(13) . . . . ?
N4 C7 C8 N1 59.9(2) . . . . ?
C1 N1 C8 C7 -157.28(16) . . . . ?
C2 N2 C3 C4 98.60(18) . . . . ?
C3 N2 C2 C1 -82.6(2) . . . . ?
C3 C4 C11 C10 -179.16(17) . . . . ?
C4 N3 C5 C6 -179.70(15) . . . . ?
C4 N3 C5 C9 -1.9(3) . . . . ?
C5 N3 C4 C3 -178.27(15) . . . . ?
C5 N3 C4 C11 3.0(3) . . . . ?
C5 C9 C10 O9 -177.36(19) . . . . ?
C5 C9 C10 C11 3.9(3) . . . . ?
C6 N4 C7 C8 79.7(2) . . . . ?
C6 C5 C9 C10 176.02(17) . . . . ?
C7 N4 C6 C5 -102.00(17) . . . . ?
C8 N1 C1 C2 160.07(17) . . . . ?
C9 C5 C6 N4 166.65(17) . . . . ?
C9 C10 C11 C4 -2.9(3) . . . . ?
O1 Cl3 O1' O3' 170(3) . . . . ?
O1 Cl3 O3' O1' -6.4(19) . . . . ?
O2 Cl3 O1' O3' -112.9(19) . . . . ?
O2 Cl3 O3' O1' 117.8(17) . . . . ?
O3 Cl3 O1' O3' -9.2(18) . . . . ?
O3 Cl3 O3' O1' 120(8) . . . . ?
O4 Cl3 O1' O3' 89(2) . . . . ?
O4 Cl3 O3' O1' -122.4(17) . . . . ?
O2' Cl3 O1' O3' -98.1(15) . . . . ?
O2' Cl3 O3' O1' 111(2) . . . . ?
O4' Cl3 O1' O3' 96(2) . . . . ?
O4' Cl3 O3' O1' -132(2) . . . . ?
O1" Cl3 O1' O3' 124(2) . . . . ?
O1" Cl3 O3' O1' -34.5(16) . . . . ?
O2" Cl3 O1' O3' -150.8(14) . . . . ?
O2" Cl3 O3' O1' 102(2) . . . . ?
O3" Cl3 O1' O3' -51.1(16) . . . . ?
O3" Cl3 O3' O1' 78.3(17) . . . . ?
O4" Cl3 O1' O3' 49(2) . . . . ?
O4" Cl3 O3' O1' -145.3(17) . . . . ?
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/c 1 1'
_symmetry_int_tables_number      14
_chemical_absolute_configuration unk





data_111512_0m
_database_code_depnum_ccdc_archive 'CCDC 911804'
#TrackingRef '15564_web_deposit_cif_file_0_KaylaGreen_1353451566.111512_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C11 H21 Cl2 N4 O5 Zn'
_chemical_formula_sum            'C11 H21 Cl2 N4 O5 Zn'
_chemical_melting_point          ?

_exptl_crystal_description       ?
_exptl_crystal_colour            'light yellow'

_diffrn_ambient_temperature      89(2)
_chemical_formula_weight         425.59

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'
Zn Zn 0.2839 1.4301 '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/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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

_cell_length_a                   11.5092(5)
_cell_length_b                   9.0075(4)
_cell_length_c                   15.4711(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.410(2)
_cell_angle_gamma                90.00
_cell_volume                     1590.48(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    89(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.0421
_exptl_crystal_size_mid          0.0221
_exptl_crystal_size_min          0.019
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             876
_exptl_absorpt_coefficient_mu    1.910
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'D8 Quest'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            91677
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         38.45
_reflns_number_total             8871
_reflns_number_gt                6731
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0586P)^2^+2.2207P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8871
_refine_ls_number_parameters     239
_refine_ls_number_restraints     47
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.276
_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
Zn1 Zn 1.01888(2) 0.68364(3) 0.155186(15) 0.01626(7) Uani 1 1 d . A 1
Cl1 Cl 1.13497(5) 0.49534(7) 0.13273(4) 0.02708(12) Uani 1 1 d . A 1
C1 C 0.84739(15) 0.8816(2) 0.05739(12) 0.0133(3) Uani 1 1 d . A 1
C2 C 0.79022(18) 1.0125(2) 0.03260(13) 0.0183(3) Uani 1 1 d . A 1
H2 H 0.7146 1.0116 -0.0003 0.022 Uiso 1 1 calc R A 1
C3 C 0.8462(2) 1.1461(2) 0.05707(14) 0.0232(4) Uani 1 1 d . A 1
C4 C 0.9549(2) 1.1439(2) 0.10945(13) 0.0201(3) Uani 1 1 d . A 1
H4 H 0.9932 1.2337 0.1287 0.024 Uiso 1 1 calc R A 1
C5 C 1.00501(16) 1.0080(2) 0.13243(13) 0.0159(3) Uani 1 1 d . A 1
C6 C 1.12073(17) 0.9930(3) 0.19037(14) 0.0211(4) Uani 1 1 d . A 1
H6A H 1.1855 1.0099 0.1552 0.025 Uiso 1 1 calc R A 1
H6B H 1.1258 1.0701 0.2363 0.025 Uiso 1 1 calc R A 1
C7 C 1.09762(19) 0.8354(3) 0.31953(14) 0.0241(4) Uani 1 1 d . A 1
H7A H 1.1214 0.9270 0.3525 0.029 Uiso 1 1 calc R A 1
H7B H 1.1375 0.7504 0.3513 0.029 Uiso 1 1 calc R A 1
C8 C 0.96578(19) 0.8158(3) 0.31451(14) 0.0202(4) Uani 1 1 d . A 1
H8A H 0.9435 0.8078 0.3740 0.024 Uiso 1 1 calc R A 1
H8B H 0.9254 0.9033 0.2858 0.024 Uiso 1 1 calc R A 1
C9 C 0.80325(18) 0.6717(3) 0.23253(14) 0.0205(4) Uani 1 1 d . A 1
H9A H 0.7737 0.7713 0.2135 0.025 Uiso 1 1 calc R A 1
H9B H 0.7598 0.6379 0.2801 0.025 Uiso 1 1 calc R A 1
C10 C 0.7834(2) 0.5637(3) 0.15660(15) 0.0218(4) Uani 1 1 d . A 1
H10A H 0.8090 0.4632 0.1767 0.026 Uiso 1 1 calc R A 1
H10B H 0.6987 0.5593 0.1347 0.026 Uiso 1 1 calc R A 1
C11 C 0.79441(16) 0.7322(2) 0.03163(13) 0.0162(3) Uani 1 1 d . A 1
H11A H 0.7096 0.7348 0.0370 0.019 Uiso 1 1 calc R A 1
H11B H 0.8029 0.7128 -0.0302 0.019 Uiso 1 1 calc R A 1
N1 N 0.95362(13) 0.88022(19) 0.10430(10) 0.0143(3) Uani 1 1 d . A 1
N2 N 1.13462(15) 0.8449(2) 0.23171(12) 0.0207(3) Uani 1 1 d . A 1
H1A H 1.1628 0.7683 0.2059 0.025 Uiso 1 1 d R A 1
N3 N 0.92960(16) 0.6802(2) 0.26438(12) 0.0182(3) Uani 1 1 d . A 1
H2A H 0.9794 0.6101 0.2543 0.022 Uiso 1 1 d R A 1
N4 N 0.84919(15) 0.61019(19) 0.08537(11) 0.0165(3) Uani 1 1 d . A 1
H3A H 0.9155 0.5685 0.0759 0.020 Uiso 1 1 d R A 1
O1 O 0.7991(2) 1.2789(2) 0.03501(16) 0.0456(7) Uani 1 1 d . A 1
H1 H 0.7335 1.2672 0.0051 0.068 Uiso 1 1 calc R A 1
Cl2 Cl 0.5314(4) 0.1919(8) 0.8803(4) 0.0219(11) Uani 0.539(4) 1 d PD B 1
O2 O 0.6254(3) 0.1224(6) 0.8510(3) 0.0408(12) Uani 0.539(4) 1 d PDU B 1
O3 O 0.4306(4) 0.0918(5) 0.8796(3) 0.0367(9) Uiso 0.539(4) 1 d PD B 1
O4 O 0.5099(6) 0.2702(9) 0.9581(3) 0.068(2) Uani 0.539(4) 1 d PDU B 1
O5 O 0.4624(4) 0.2444(7) 0.8066(3) 0.0426(12) Uani 0.539(4) 1 d PDU B 1
Cl2' Cl 0.5309(4) 0.2004(9) 0.8808(4) 0.0172(9) Uani 0.461(4) 1 d P B 2
O2' O 0.6562(3) 0.2339(4) 0.8755(2) 0.0237(8) Uiso 0.461(4) 1 d P B 2
O3' O 0.5272(6) 0.0403(6) 0.8984(3) 0.0505(17) Uani 0.461(4) 1 d PU B 2
O4' O 0.5608(5) 0.2579(6) 0.9630(3) 0.0307(10) Uiso 0.461(4) 1 d P B 2
O5' O 0.4901(5) 0.3156(6) 0.8196(4) 0.0343(10) Uiso 0.461(4) 1 d P B 2

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
Zn1 0.01254(10) 0.02041(12) 0.01528(10) -0.00041(8) -0.00034(7) 0.00627(7)
Cl1 0.0208(2) 0.0314(3) 0.0274(2) -0.0071(2) -0.00299(18) 0.01422(19)
C1 0.0117(6) 0.0149(7) 0.0127(6) -0.0003(5) -0.0008(5) 0.0009(5)
C2 0.0198(8) 0.0164(8) 0.0165(8) -0.0001(6) -0.0061(6) 0.0025(6)
C3 0.0332(11) 0.0151(8) 0.0184(8) 0.0015(7) -0.0080(7) 0.0004(7)
C4 0.0243(9) 0.0178(8) 0.0168(8) 0.0002(6) -0.0019(7) -0.0057(7)
C5 0.0124(7) 0.0209(8) 0.0144(7) -0.0019(6) 0.0014(5) -0.0038(6)
C6 0.0121(7) 0.0297(10) 0.0207(8) -0.0028(7) -0.0007(6) -0.0043(7)
C7 0.0173(8) 0.0375(12) 0.0158(8) -0.0011(8) -0.0041(6) -0.0003(8)
C8 0.0182(8) 0.0267(10) 0.0153(8) -0.0023(7) 0.0010(6) 0.0003(7)
C9 0.0158(8) 0.0257(10) 0.0203(8) 0.0004(7) 0.0035(6) -0.0007(7)
C10 0.0219(9) 0.0198(9) 0.0234(9) 0.0010(7) 0.0022(7) -0.0046(7)
C11 0.0133(7) 0.0153(7) 0.0184(8) -0.0018(6) -0.0037(6) 0.0019(6)
N1 0.0105(5) 0.0175(7) 0.0144(6) -0.0010(5) -0.0005(5) 0.0002(5)
N2 0.0108(6) 0.0314(9) 0.0190(7) -0.0017(7) -0.0021(5) 0.0025(6)
N3 0.0161(7) 0.0214(8) 0.0168(7) 0.0009(6) 0.0001(5) 0.0026(5)
N4 0.0156(6) 0.0141(6) 0.0191(7) 0.0000(5) 0.0001(5) 0.0031(5)
O1 0.0648(15) 0.0144(7) 0.0463(12) -0.0004(8) -0.0353(11) 0.0044(8)
Cl2 0.0256(17) 0.0241(15) 0.0166(16) -0.0055(11) 0.0044(10) -0.0011(9)
O2 0.0264(16) 0.069(3) 0.0275(17) -0.0079(18) 0.0052(13) 0.0252(18)
O4 0.055(4) 0.116(5) 0.035(2) -0.043(3) 0.010(2) -0.003(4)
O5 0.0236(17) 0.075(4) 0.0250(17) 0.003(2) -0.0115(13) 0.016(2)
Cl2' 0.0101(13) 0.0204(13) 0.022(2) 0.0041(12) 0.0037(10) 0.0022(8)
O3' 0.076(4) 0.032(2) 0.035(2) 0.0132(19) -0.023(2) -0.033(2)

_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
Zn1 N1 2.0413(17) . ?
Zn1 N3 2.0876(19) . ?
Zn1 N4 2.2078(17) . ?
Zn1 N2 2.2092(19) . ?
Zn1 Cl1 2.2141(6) . ?
Zn1 H1A 1.8991 . ?
Zn1 H2A 1.7826 . ?
Zn1 H3A 1.9028 . ?
C1 N1 1.339(2) . ?
C1 C2 1.381(3) . ?
C1 C11 1.509(3) . ?
C2 C3 1.394(3) . ?
C2 H2 0.9500 . ?
C3 O1 1.340(3) . ?
C3 C4 1.400(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.341(3) . ?
C5 C6 1.512(3) . ?
C6 N2 1.479(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.478(3) . ?
C7 C8 1.520(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N3 1.478(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.476(3) . ?
C9 C10 1.520(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N4 1.476(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N4 1.470(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N2 H1A 0.8800 . ?
N3 H2A 0.8800 . ?
N4 H3A 0.8800 . ?
O1 H1 0.8400 . ?
Cl2 O2 1.377(6) . ?
Cl2 O5 1.385(7) . ?
Cl2 O4 1.444(7) . ?
Cl2 O3 1.468(7) . ?
Cl2' O4' 1.375(8) . ?
Cl2' O5' 1.441(9) . ?
Cl2' O3' 1.470(9) . ?
Cl2' O2' 1.486(6) . ?

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 Zn1 N3 97.47(7) . . ?
N1 Zn1 N4 79.22(6) . . ?
N3 Zn1 N4 83.96(7) . . ?
N1 Zn1 N2 78.62(7) . . ?
N3 Zn1 N2 84.37(7) . . ?
N4 Zn1 N2 153.31(7) . . ?
N1 Zn1 Cl1 143.46(5) . . ?
N3 Zn1 Cl1 119.04(5) . . ?
N4 Zn1 Cl1 101.96(5) . . ?
N2 Zn1 Cl1 104.69(5) . . ?
N1 Zn1 H1A 94.0 . . ?
N3 Zn1 H1A 99.5 . . ?
N4 Zn1 H1A 172.7 . . ?
N2 Zn1 H1A 23.2 . . ?
Cl1 Zn1 H1A 82.0 . . ?
N1 Zn1 H2A 122.2 . . ?
N3 Zn1 H2A 24.7 . . ?
N4 Zn1 H2A 90.1 . . ?
N2 Zn1 H2A 89.2 . . ?
Cl1 Zn1 H2A 94.4 . . ?
H1A Zn1 H2A 95.7 . . ?
N1 Zn1 H3A 93.2 . . ?
N3 Zn1 H3A 100.5 . . ?
N4 Zn1 H3A 23.2 . . ?
N2 Zn1 H3A 171.0 . . ?
Cl1 Zn1 H3A 79.7 . . ?
H1A Zn1 H3A 157.7 . . ?
H2A Zn1 H3A 98.3 . . ?
N1 C1 C2 121.84(17) . . ?
N1 C1 C11 116.39(16) . . ?
C2 C1 C11 121.76(16) . . ?
C1 C2 C3 118.33(18) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
O1 C3 C2 122.9(2) . . ?
O1 C3 C4 117.5(2) . . ?
C2 C3 C4 119.5(2) . . ?
C5 C4 C3 118.27(19) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N1 C5 C4 121.71(17) . . ?
N1 C5 C6 115.71(18) . . ?
C4 C5 C6 122.57(18) . . ?
N2 C6 C5 111.99(17) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C8 111.35(16) . . ?
N2 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N2 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N3 C8 C7 109.55(18) . . ?
N3 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
N3 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N3 C9 C10 109.55(18) . . ?
N3 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
N3 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
N4 C10 C9 110.80(17) . . ?
N4 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N4 C11 C1 112.82(15) . . ?
N4 C11 H11A 109.0 . . ?
C1 C11 H11A 109.0 . . ?
N4 C11 H11B 109.0 . . ?
C1 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C1 N1 C5 120.13(17) . . ?
C1 N1 Zn1 118.81(13) . . ?
C5 N1 Zn1 119.63(13) . . ?
C7 N2 C6 114.97(19) . . ?
C7 N2 Zn1 103.24(14) . . ?
C6 N2 Zn1 109.71(12) . . ?
C7 N2 H1A 122.5 . . ?
C6 N2 H1A 122.5 . . ?
Zn1 N2 H1A 58.2 . . ?
C9 N3 C8 114.61(17) . . ?
C9 N3 Zn1 107.29(13) . . ?
C8 N3 Zn1 106.11(13) . . ?
C9 N3 H2A 122.7 . . ?
C8 N3 H2A 122.7 . . ?
Zn1 N3 H2A 57.9 . . ?
C11 N4 C10 114.21(16) . . ?
C11 N4 Zn1 109.91(12) . . ?
C10 N4 Zn1 103.09(12) . . ?
C11 N4 H3A 122.9 . . ?
C10 N4 H3A 122.9 . . ?
Zn1 N4 H3A 58.5 . . ?
O2 Cl2 O5 106.0(4) . . ?
O2 Cl2 O4 136.3(5) . . ?
O5 Cl2 O4 112.2(6) . . ?
O2 Cl2 O3 111.8(5) . . ?
O5 Cl2 O3 80.5(4) . . ?
O4 Cl2 O3 95.0(5) . . ?
O4' Cl2' O5' 111.0(6) . . ?
O4' Cl2' O3' 102.0(5) . . ?
O5' Cl2' O3' 144.4(6) . . ?
O4' Cl2' O2' 81.1(4) . . ?
O5' Cl2' O2' 93.1(5) . . ?
O3' Cl2' O2' 105.1(5) . . ?

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 0.5(3) . . . . ?
C11 C1 C2 C3 -178.4(2) . . . . ?
C1 C2 C3 O1 178.8(3) . . . . ?
C1 C2 C3 C4 -3.4(3) . . . . ?
O1 C3 C4 C5 -179.7(2) . . . . ?
C2 C3 C4 C5 2.4(3) . . . . ?
C3 C4 C5 N1 1.5(3) . . . . ?
C3 C4 C5 C6 -178.6(2) . . . . ?
N1 C5 C6 N2 -21.4(3) . . . . ?
C4 C5 C6 N2 158.7(2) . . . . ?
N2 C7 C8 N3 58.3(3) . . . . ?
N3 C9 C10 N4 -58.3(2) . . . . ?
N1 C1 C11 N4 19.0(2) . . . . ?
C2 C1 C11 N4 -162.12(19) . . . . ?
C2 C1 N1 C5 3.4(3) . . . . ?
C11 C1 N1 C5 -177.64(17) . . . . ?
C2 C1 N1 Zn1 169.73(15) . . . . ?
C11 C1 N1 Zn1 -11.3(2) . . . . ?
C4 C5 N1 C1 -4.5(3) . . . . ?
C6 C5 N1 C1 175.64(17) . . . . ?
C4 C5 N1 Zn1 -170.66(16) . . . . ?
C6 C5 N1 Zn1 9.5(2) . . . . ?
N3 Zn1 N1 C1 -81.12(15) . . . . ?
N4 Zn1 N1 C1 1.24(14) . . . . ?
N2 Zn1 N1 C1 -163.80(15) . . . . ?
Cl1 Zn1 N1 C1 96.83(15) . . . . ?
N3 Zn1 N1 C5 85.24(15) . . . . ?
N4 Zn1 N1 C5 167.60(15) . . . . ?
N2 Zn1 N1 C5 2.56(14) . . . . ?
Cl1 Zn1 N1 C5 -96.81(15) . . . . ?
C8 C7 N2 C6 81.6(2) . . . . ?
C8 C7 N2 Zn1 -37.8(2) . . . . ?
C5 C6 N2 C7 -93.8(2) . . . . ?
C5 C6 N2 Zn1 22.0(2) . . . . ?
N1 Zn1 N2 C7 109.27(14) . . . . ?
N3 Zn1 N2 C7 10.46(14) . . . . ?
N4 Zn1 N2 C7 74.9(2) . . . . ?
Cl1 Zn1 N2 C7 -108.12(13) . . . . ?
N1 Zn1 N2 C6 -13.76(13) . . . . ?
N3 Zn1 N2 C6 -112.56(14) . . . . ?
N4 Zn1 N2 C6 -48.1(2) . . . . ?
Cl1 Zn1 N2 C6 128.85(13) . . . . ?
C10 C9 N3 C8 158.96(18) . . . . ?
C10 C9 N3 Zn1 41.42(19) . . . . ?
C7 C8 N3 C9 -162.71(18) . . . . ?
C7 C8 N3 Zn1 -44.51(19) . . . . ?
N1 Zn1 N3 C9 63.64(14) . . . . ?
N4 Zn1 N3 C9 -14.62(14) . . . . ?
N2 Zn1 N3 C9 141.34(14) . . . . ?
Cl1 Zn1 N3 C9 -114.97(13) . . . . ?
N1 Zn1 N3 C8 -59.32(13) . . . . ?
N4 Zn1 N3 C8 -137.57(13) . . . . ?
N2 Zn1 N3 C8 18.39(13) . . . . ?
Cl1 Zn1 N3 C8 122.08(12) . . . . ?
C1 C11 N4 C10 98.6(2) . . . . ?
C1 C11 N4 Zn1 -16.70(19) . . . . ?
C9 C10 N4 C11 -78.1(2) . . . . ?
C9 C10 N4 Zn1 41.13(19) . . . . ?
N1 Zn1 N4 C11 8.91(13) . . . . ?
N3 Zn1 N4 C11 107.72(13) . . . . ?
N2 Zn1 N4 C11 43.2(2) . . . . ?
Cl1 Zn1 N4 C11 -133.81(12) . . . . ?
N1 Zn1 N4 C10 -113.23(13) . . . . ?
N3 Zn1 N4 C10 -14.42(13) . . . . ?
N2 Zn1 N4 C10 -78.9(2) . . . . ?
Cl1 Zn1 N4 C10 104.04(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        38.45
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.525
_refine_diff_density_min         -1.152
_refine_diff_density_rms         0.126