# Electronic Supplementary Material (ESI) for RSC Advances
# 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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#  fide research purposes only. It may contain copyright material
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data_mo_111219a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H26 Cl N4 O6 Zn'
_chemical_formula_weight         555.30

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'
Zn Zn 0.2839 1.4301 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   14.6762(14)
_cell_length_b                   8.8145(8)
_cell_length_c                   17.7485(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.436(2)
_cell_angle_gamma                90.00
_cell_volume                     2293.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3218
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.70

_exptl_crystal_description       ?
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1148
_exptl_absorpt_coefficient_mu    1.237
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15921
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4489
_reflns_number_gt                3471
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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^)+(0.0668P)^2^+0.4650P] 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     SHELXL
_refine_ls_extinction_coef       0.0030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4489
_refine_ls_number_parameters     334
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.023

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 0.68062(2) 0.84952(4) 0.92061(2) 0.01622(14) Uani 1 1 d . . .
C1 C 0.9075(2) 0.8854(4) 0.86764(19) 0.0178(7) Uani 1 1 d . . .
H1 H 0.8709 0.7968 0.8701 0.021 Uiso 1 1 calc R . .
C2 C 0.9153(2) 0.9555(4) 0.80033(19) 0.0213(7) Uani 1 1 d . . .
H2A H 0.8850 0.9150 0.7565 0.026 Uiso 1 1 calc R . .
C3 C 0.9685(2) 1.0891(4) 0.7950(2) 0.0230(7) Uani 1 1 d . . .
H3 H 0.9721 1.1403 0.7481 0.028 Uiso 1 1 calc R . .
C4 C 1.0144(2) 1.1433(4) 0.85739(19) 0.0184(7) Uani 1 1 d . . .
H4 H 1.0510 1.2314 0.8528 0.022 Uiso 1 1 calc R . .
C5 C 1.00954(19) 1.0730(4) 0.92966(18) 0.0157(7) Uani 1 1 d . . .
C6 C 0.95281(18) 0.9405(3) 0.93517(17) 0.0142(6) Uani 1 1 d . . .
C7 C 0.94218(19) 0.8712(3) 1.00552(18) 0.0143(6) Uani 1 1 d . . .
C8 C 0.8774(2) 0.7371(4) 1.01318(18) 0.0166(7) Uani 1 1 d . . .
H8A H 0.8785 0.6751 0.9667 0.020 Uiso 1 1 calc R . .
H8B H 0.9000 0.6729 1.0557 0.020 Uiso 1 1 calc R . .
C9 C 0.7709(2) 0.9180(4) 1.07349(17) 0.0152(6) Uani 1 1 d . . .
H9A H 0.8182 0.9172 1.1150 0.018 Uiso 1 1 calc R . .
H9B H 0.7103 0.9187 1.0959 0.018 Uiso 1 1 calc R . .
C10 C 0.78168(19) 1.0573(4) 1.02561(18) 0.0157(7) Uani 1 1 d . . .
C11 C 0.8308(2) 1.1830(4) 1.0503(2) 0.0195(7) Uani 1 1 d . . .
H11 H 0.8542 1.1895 1.1010 0.023 Uiso 1 1 calc R . .
C12 C 0.8454(2) 1.2995(4) 0.9994(2) 0.0235(8) Uani 1 1 d . . .
H12 H 0.8797 1.3864 1.0148 0.028 Uiso 1 1 calc R . .
C13 C 0.8097(2) 1.2884(4) 0.9265(2) 0.0213(7) Uani 1 1 d . . .
H13 H 0.8209 1.3655 0.8906 0.026 Uiso 1 1 calc R . .
C14 C 0.7573(2) 1.1626(4) 0.90627(18) 0.0174(7) Uani 1 1 d . . .
C15 C 0.7133(2) 1.1448(4) 0.8289(2) 0.0228(7) Uani 1 1 d . . .
H15A H 0.6562 1.2047 0.8249 0.027 Uiso 1 1 calc R . .
H15B H 0.7548 1.1829 0.7906 0.027 Uiso 1 1 calc R . .
C16 C 0.7350(2) 0.6499(4) 1.05906(19) 0.0184(7) Uani 1 1 d . . .
H16A H 0.7576 0.6374 1.1121 0.022 Uiso 1 1 calc R . .
H16B H 0.7515 0.5574 1.0311 0.022 Uiso 1 1 calc R . .
C17 C 0.6329(2) 0.6656(4) 1.05691(19) 0.0175(7) Uani 1 1 d . . .
C18 C 0.5798(2) 0.5877(4) 1.10637(19) 0.0221(7) Uani 1 1 d . . .
H18 H 0.6073 0.5313 1.1469 0.027 Uiso 1 1 calc R . .
C19 C 0.4859(2) 0.5929(4) 1.0961(2) 0.0256(8) Uani 1 1 d . . .
H19 H 0.4483 0.5378 1.1287 0.031 Uiso 1 1 calc R . .
C20 C 0.4476(2) 0.6781(4) 1.0386(2) 0.0243(8) Uani 1 1 d . . .
H20 H 0.3832 0.6814 1.0301 0.029 Uiso 1 1 calc R . .
C21 C 0.5043(2) 0.7597(4) 0.99275(19) 0.0199(7) Uani 1 1 d . . .
C22 C 0.4669(2) 0.8579(4) 0.9298(2) 0.0238(8) Uani 1 1 d . . .
H22A H 0.4335 0.7948 0.8917 0.029 Uiso 1 1 calc R . .
H22B H 0.4239 0.9330 0.9496 0.029 Uiso 1 1 calc R . .
Cl1 Cl 0.70767(5) 0.63221(9) 0.85764(4) 0.0209(2) Uani 1 1 d . . .
N1 N 0.74339(16) 1.0493(3) 0.95555(15) 0.0150(6) Uani 1 1 d . . .
N2 N 0.78009(16) 0.7813(3) 1.02619(14) 0.0139(6) Uani 1 1 d . . .
N3 N 0.59516(16) 0.7521(3) 1.00186(14) 0.0165(6) Uani 1 1 d . . .
N4 N 0.0136(2) 0.5354(4) 0.7912(2) 0.0356(8) Uani 1 1 d . . .
O1 O 0.69362(15) 0.9889(3) 0.81541(13) 0.0231(5) Uani 1 1 d D . .
H1A H 0.661(2) 0.976(5) 0.7771(14) 0.035 Uiso 1 1 d D . .
O2 O 0.53986(15) 0.9338(3) 0.89618(14) 0.0289(6) Uani 1 1 d D . .
H2 H 0.520(3) 0.963(5) 0.8544(12) 0.043 Uiso 1 1 d D . .
O3 O -0.0655(2) 0.4938(3) 0.80151(17) 0.0432(7) Uani 1 1 d . . .
O4 O 0.0704(2) 0.5488(4) 0.84412(17) 0.0516(9) Uani 1 1 d . . .
O5 O 0.0365(2) 0.5702(5) 0.72494(18) 0.0593(10) Uani 1 1 d . . .
C23 C 0.2306(6) 0.1792(11) 0.7182(6) 0.073(3) Uani 0.730(6) 1 d PDU A 1
H23A H 0.2352 0.0740 0.7359 0.110 Uiso 0.730(6) 1 calc PR A 1
H23B H 0.2369 0.1821 0.6635 0.110 Uiso 0.730(6) 1 calc PR A 1
H23C H 0.1712 0.2210 0.7305 0.110 Uiso 0.730(6) 1 calc PR A 1
O6 O 0.3030(3) 0.2693(6) 0.7551(3) 0.0611(15) Uani 0.730(6) 1 d PD A 1
H6 H 0.3537 0.2408 0.7401 0.092 Uiso 0.730(6) 1 calc PR A 1
C23' C 0.246(2) 0.1010(19) 0.7287(18) 0.073(3) Uani 0.270(6) 1 d PD A 2
H23D H 0.2954 0.0808 0.7666 0.110 Uiso 0.270(6) 1 calc PR A 2
H23E H 0.2654 0.0671 0.6792 0.110 Uiso 0.270(6) 1 calc PR A 2
H23F H 0.1914 0.0461 0.7420 0.110 Uiso 0.270(6) 1 calc PR A 2
O6' O 0.2276(10) 0.2628(18) 0.7262(9) 0.0611(15) Uani 0.270(6) 1 d PD A 2
H6' H 0.1713 0.2772 0.7294 0.092 Uiso 0.270(6) 1 calc PR A 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 0.0132(2) 0.0175(2) 0.0180(2) -0.00006(16) 0.00166(13) -0.00134(15)
C1 0.0125(14) 0.0187(17) 0.0225(18) -0.0034(14) 0.0038(12) -0.0037(12)
C2 0.0181(16) 0.0270(19) 0.0185(18) -0.0035(15) -0.0001(13) -0.0035(14)
C3 0.0220(17) 0.0244(18) 0.0227(18) 0.0029(15) 0.0020(14) -0.0017(14)
C4 0.0118(14) 0.0183(17) 0.0252(18) 0.0042(14) 0.0017(12) -0.0035(13)
C5 0.0093(14) 0.0156(16) 0.0224(17) 0.0011(14) 0.0015(12) 0.0007(12)
C6 0.0088(13) 0.0134(15) 0.0204(17) -0.0002(13) 0.0005(11) 0.0028(12)
C7 0.0096(14) 0.0124(15) 0.0211(17) 0.0010(13) 0.0010(12) 0.0013(11)
C8 0.0124(14) 0.0148(16) 0.0226(17) 0.0002(14) 0.0013(12) 0.0005(12)
C9 0.0117(14) 0.0158(16) 0.0180(16) -0.0002(13) 0.0010(12) -0.0015(12)
C10 0.0113(14) 0.0154(16) 0.0205(17) 0.0004(13) 0.0024(12) 0.0021(12)
C11 0.0178(15) 0.0150(17) 0.0260(18) -0.0018(14) 0.0040(13) 0.0018(13)
C12 0.0183(16) 0.0150(17) 0.038(2) -0.0033(15) 0.0055(15) 0.0009(13)
C13 0.0232(17) 0.0120(16) 0.030(2) 0.0048(14) 0.0106(14) 0.0032(13)
C14 0.0182(15) 0.0138(16) 0.0210(17) 0.0044(14) 0.0086(13) 0.0048(13)
C15 0.0255(17) 0.0192(17) 0.0240(18) 0.0012(15) 0.0029(14) 0.0045(14)
C16 0.0170(15) 0.0157(16) 0.0226(17) 0.0039(14) 0.0023(13) -0.0040(13)
C17 0.0173(15) 0.0126(16) 0.0227(17) -0.0049(14) 0.0035(13) -0.0041(13)
C18 0.0257(17) 0.0192(17) 0.0217(18) -0.0008(15) 0.0035(14) -0.0065(14)
C19 0.0237(18) 0.0267(19) 0.027(2) -0.0044(16) 0.0140(15) -0.0097(15)
C20 0.0159(16) 0.026(2) 0.031(2) -0.0092(16) 0.0076(14) -0.0041(14)
C21 0.0166(15) 0.0184(17) 0.0249(18) -0.0095(14) 0.0039(13) -0.0037(13)
C22 0.0122(15) 0.0294(19) 0.030(2) -0.0028(16) 0.0007(13) -0.0011(14)
Cl1 0.0207(4) 0.0212(4) 0.0210(4) -0.0025(3) 0.0027(3) -0.0027(3)
N1 0.0118(12) 0.0149(13) 0.0187(14) 0.0014(11) 0.0046(10) 0.0030(10)
N2 0.0107(12) 0.0122(13) 0.0188(14) 0.0010(11) 0.0019(10) -0.0012(10)
N3 0.0120(12) 0.0186(14) 0.0190(14) -0.0045(12) 0.0039(10) -0.0041(11)
N4 0.042(2) 0.0244(17) 0.039(2) 0.0030(15) -0.0144(16) 0.0004(15)
O1 0.0240(13) 0.0258(13) 0.0191(13) 0.0022(11) -0.0024(10) -0.0020(10)
O2 0.0174(12) 0.0423(16) 0.0272(14) 0.0117(13) 0.0022(10) 0.0024(11)
O3 0.0444(17) 0.0453(18) 0.0390(17) 0.0134(14) -0.0093(13) -0.0128(14)
O4 0.062(2) 0.0429(19) 0.0472(19) 0.0036(15) -0.0337(15) -0.0092(16)
O5 0.0461(18) 0.097(3) 0.0347(19) -0.0118(19) -0.0019(14) -0.0205(19)
C23 0.072(5) 0.080(7) 0.069(5) 0.007(6) 0.009(4) -0.027(6)
O6 0.044(2) 0.089(4) 0.050(3) -0.025(3) -0.004(2) -0.003(3)
C23' 0.072(5) 0.080(7) 0.069(5) 0.007(6) 0.009(4) -0.027(6)
O6' 0.044(2) 0.089(4) 0.050(3) -0.025(3) -0.004(2) -0.003(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.070(3) . ?
Zn1 N3 2.132(3) . ?
Zn1 O2 2.221(2) . ?
Zn1 O1 2.250(2) . ?
Zn1 Cl1 2.2613(9) . ?
Zn1 N2 2.402(3) . ?
C1 C2 1.354(5) . ?
C1 C6 1.430(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.418(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.359(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.429(5) . ?
C4 H4 0.9500 . ?
C5 C7 1.414(4) 3_777 ?
C5 C6 1.440(4) . ?
C6 C7 1.405(4) . ?
C7 C5 1.414(4) 3_777 ?
C7 C8 1.527(4) . ?
C8 N2 1.507(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.478(4) . ?
C9 C10 1.506(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N1 1.344(4) . ?
C10 C11 1.383(4) . ?
C11 C12 1.390(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(5) . ?
C13 H13 0.9500 . ?
C14 N1 1.349(4) . ?
C14 C15 1.501(5) . ?
C15 O1 1.422(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N2 1.468(4) . ?
C16 C17 1.504(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N3 1.341(4) . ?
C17 C18 1.381(5) . ?
C18 C19 1.383(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.369(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(5) . ?
C20 H20 0.9500 . ?
C21 N3 1.339(4) . ?
C21 C22 1.499(5) . ?
C22 O2 1.415(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N4 O4 1.234(4) . ?
N4 O3 1.238(4) . ?
N4 O5 1.274(4) . ?
O1 H1A 0.822(10) . ?
O2 H2 0.824(10) . ?
C23 O6 1.459(7) . ?
C23 H23A 0.9801 . ?
C23 H23B 0.9801 . ?
C23 H23C 0.9801 . ?
O6 H6 0.8400 . ?
C23' O6' 1.453(10) . ?
C23' H23D 0.9800 . ?
C23' H23E 0.9800 . ?
C23' H23F 0.9800 . ?
O6' H6' 0.8480 . ?

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 114.02(10) . . ?
N1 Zn1 O2 99.93(10) . . ?
N3 Zn1 O2 72.39(9) . . ?
N1 Zn1 O1 74.45(9) . . ?
N3 Zn1 O1 148.70(9) . . ?
O2 Zn1 O1 76.49(9) . . ?
N1 Zn1 Cl1 141.57(7) . . ?
N3 Zn1 Cl1 96.54(8) . . ?
O2 Zn1 Cl1 111.61(8) . . ?
O1 Zn1 Cl1 91.69(7) . . ?
N1 Zn1 N2 74.40(9) . . ?
N3 Zn1 N2 74.16(9) . . ?
O2 Zn1 N2 139.94(9) . . ?
O1 Zn1 N2 135.54(8) . . ?
Cl1 Zn1 N2 93.44(7) . . ?
C2 C1 C6 122.0(3) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 122.5(3) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C7 C5 C4 122.5(3) 3_777 . ?
C7 C5 C6 119.9(3) 3_777 . ?
C4 C5 C6 117.6(3) . . ?
C7 C6 C1 122.1(3) . . ?
C7 C6 C5 120.0(3) . . ?
C1 C6 C5 117.9(3) . . ?
C6 C7 C5 120.1(3) . 3_777 ?
C6 C7 C8 120.6(3) . . ?
C5 C7 C8 119.3(3) 3_777 . ?
N2 C8 C7 114.3(2) . . ?
N2 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
N2 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N2 C9 C10 109.3(2) . . ?
N2 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
N2 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
N1 C10 C11 121.8(3) . . ?
N1 C10 C9 115.4(3) . . ?
C11 C10 C9 122.7(3) . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
N1 C14 C13 121.4(3) . . ?
N1 C14 C15 116.4(3) . . ?
C13 C14 C15 122.2(3) . . ?
O1 C15 C14 109.3(3) . . ?
O1 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
O1 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N2 C16 C17 112.5(3) . . ?
N2 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
N2 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
N3 C17 C18 121.3(3) . . ?
N3 C17 C16 116.8(3) . . ?
C18 C17 C16 121.8(3) . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C20 C19 C18 119.5(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 118.9(3) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
N3 C21 C20 121.5(3) . . ?
N3 C21 C22 116.7(3) . . ?
C20 C21 C22 121.8(3) . . ?
O2 C22 C21 109.1(3) . . ?
O2 C22 H22A 109.9 . . ?
C21 C22 H22A 109.9 . . ?
O2 C22 H22B 109.8 . . ?
C21 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
C10 N1 C14 119.5(3) . . ?
C10 N1 Zn1 119.0(2) . . ?
C14 N1 Zn1 120.9(2) . . ?
C16 N2 C9 111.4(2) . . ?
C16 N2 C8 107.6(2) . . ?
C9 N2 C8 114.1(2) . . ?
C16 N2 Zn1 103.78(18) . . ?
C9 N2 Zn1 99.92(17) . . ?
C8 N2 Zn1 119.57(19) . . ?
C21 N3 C17 119.7(3) . . ?
C21 N3 Zn1 120.7(2) . . ?
C17 N3 Zn1 119.1(2) . . ?
O4 N4 O3 121.5(4) . . ?
O4 N4 O5 118.9(3) . . ?
O3 N4 O5 119.6(3) . . ?
C15 O1 Zn1 114.3(2) . . ?
C15 O1 H1A 112(3) . . ?
Zn1 O1 H1A 123(3) . . ?
C22 O2 Zn1 118.3(2) . . ?
C22 O2 H2 106(3) . . ?
Zn1 O2 H2 124(3) . . ?
O6' C23' H23D 109.4 . . ?
O6' C23' H23E 109.6 . . ?
H23D C23' H23E 109.5 . . ?
O6' C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?

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
C6 C1 C2 C3 -0.9(5) . . . . ?
C1 C2 C3 C4 2.4(5) . . . . ?
C2 C3 C4 C5 -1.6(5) . . . . ?
C3 C4 C5 C7 179.5(3) . . . 3_777 ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C2 C1 C6 C7 177.6(3) . . . . ?
C2 C1 C6 C5 -1.3(5) . . . . ?
C7 C5 C6 C7 2.9(5) 3_777 . . . ?
C4 C5 C6 C7 -177.0(3) . . . . ?
C7 C5 C6 C1 -178.1(3) 3_777 . . . ?
C4 C5 C6 C1 2.0(4) . . . . ?
C1 C6 C7 C5 178.1(3) . . . 3_777 ?
C5 C6 C7 C5 -2.9(5) . . . 3_777 ?
C1 C6 C7 C8 -3.0(4) . . . . ?
C5 C6 C7 C8 175.9(3) . . . . ?
C6 C7 C8 N2 -86.8(3) . . . . ?
C5 C7 C8 N2 92.1(3) 3_777 . . . ?
N2 C9 C10 N1 38.7(3) . . . . ?
N2 C9 C10 C11 -138.6(3) . . . . ?
N1 C10 C11 C12 -4.0(5) . . . . ?
C9 C10 C11 C12 173.1(3) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C11 C12 C13 C14 2.2(5) . . . . ?
C12 C13 C14 N1 -2.5(5) . . . . ?
C12 C13 C14 C15 177.7(3) . . . . ?
N1 C14 C15 O1 -20.9(4) . . . . ?
C13 C14 C15 O1 158.8(3) . . . . ?
N2 C16 C17 N3 27.3(4) . . . . ?
N2 C16 C17 C18 -156.4(3) . . . . ?
N3 C17 C18 C19 3.6(5) . . . . ?
C16 C17 C18 C19 -172.6(3) . . . . ?
C17 C18 C19 C20 -1.8(5) . . . . ?
C18 C19 C20 C21 -1.2(5) . . . . ?
C19 C20 C21 N3 2.6(5) . . . . ?
C19 C20 C21 C22 -178.7(3) . . . . ?
N3 C21 C22 O2 -4.8(4) . . . . ?
C20 C21 C22 O2 176.4(3) . . . . ?
C11 C10 N1 C14 3.8(4) . . . . ?
C9 C10 N1 C14 -173.5(3) . . . . ?
C11 C10 N1 Zn1 174.8(2) . . . . ?
C9 C10 N1 Zn1 -2.5(3) . . . . ?
C13 C14 N1 C10 -0.5(4) . . . . ?
C15 C14 N1 C10 179.3(3) . . . . ?
C13 C14 N1 Zn1 -171.3(2) . . . . ?
C15 C14 N1 Zn1 8.5(4) . . . . ?
N3 Zn1 N1 C10 44.8(2) . . . . ?
O2 Zn1 N1 C10 119.8(2) . . . . ?
O1 Zn1 N1 C10 -167.4(2) . . . . ?
Cl1 Zn1 N1 C10 -94.9(2) . . . . ?
N2 Zn1 N1 C10 -19.5(2) . . . . ?
N3 Zn1 N1 C14 -144.4(2) . . . . ?
O2 Zn1 N1 C14 -69.4(2) . . . . ?
O1 Zn1 N1 C14 3.5(2) . . . . ?
Cl1 Zn1 N1 C14 75.9(2) . . . . ?
N2 Zn1 N1 C14 151.4(2) . . . . ?
C17 C16 N2 C9 68.5(3) . . . . ?
C17 C16 N2 C8 -165.8(3) . . . . ?
C17 C16 N2 Zn1 -38.1(3) . . . . ?
C10 C9 N2 C16 -156.8(2) . . . . ?
C10 C9 N2 C8 81.2(3) . . . . ?
C10 C9 N2 Zn1 -47.7(2) . . . . ?
C7 C8 N2 C16 -159.8(3) . . . . ?
C7 C8 N2 C9 -35.7(4) . . . . ?
C7 C8 N2 Zn1 82.3(3) . . . . ?
N1 Zn1 N2 C16 151.1(2) . . . . ?
N3 Zn1 N2 C16 29.87(18) . . . . ?
O2 Zn1 N2 C16 64.2(2) . . . . ?
O1 Zn1 N2 C16 -161.89(17) . . . . ?
Cl1 Zn1 N2 C16 -65.96(18) . . . . ?
N1 Zn1 N2 C9 36.04(17) . . . . ?
N3 Zn1 N2 C9 -85.19(17) . . . . ?
O2 Zn1 N2 C9 -50.9(2) . . . . ?
O1 Zn1 N2 C9 83.0(2) . . . . ?
Cl1 Zn1 N2 C9 178.98(16) . . . . ?
N1 Zn1 N2 C8 -89.1(2) . . . . ?
N3 Zn1 N2 C8 149.7(2) . . . . ?
O2 Zn1 N2 C8 -176.0(2) . . . . ?
O1 Zn1 N2 C8 -42.1(3) . . . . ?
Cl1 Zn1 N2 C8 53.9(2) . . . . ?
C20 C21 N3 C17 -0.8(5) . . . . ?
C22 C21 N3 C17 -179.6(3) . . . . ?
C20 C21 N3 Zn1 170.2(2) . . . . ?
C22 C21 N3 Zn1 -8.6(4) . . . . ?
C18 C17 N3 C21 -2.3(5) . . . . ?
C16 C17 N3 C21 174.0(3) . . . . ?
C18 C17 N3 Zn1 -173.5(2) . . . . ?
C16 C17 N3 Zn1 2.9(4) . . . . ?
N1 Zn1 N3 C21 105.9(2) . . . . ?
O2 Zn1 N3 C21 12.6(2) . . . . ?
O1 Zn1 N3 C21 6.2(4) . . . . ?
Cl1 Zn1 N3 C21 -98.0(2) . . . . ?
N2 Zn1 N3 C21 170.2(3) . . . . ?
N1 Zn1 N3 C17 -83.0(2) . . . . ?
O2 Zn1 N3 C17 -176.3(3) . . . . ?
O1 Zn1 N3 C17 177.3(2) . . . . ?
Cl1 Zn1 N3 C17 73.1(2) . . . . ?
N2 Zn1 N3 C17 -18.7(2) . . . . ?
C14 C15 O1 Zn1 23.2(3) . . . . ?
N1 Zn1 O1 C15 -15.4(2) . . . . ?
N3 Zn1 O1 C15 95.4(3) . . . . ?
O2 Zn1 O1 C15 89.1(2) . . . . ?
Cl1 Zn1 O1 C15 -159.1(2) . . . . ?
N2 Zn1 O1 C15 -62.4(3) . . . . ?
C21 C22 O2 Zn1 15.5(4) . . . . ?
N1 Zn1 O2 C22 -127.6(2) . . . . ?
N3 Zn1 O2 C22 -15.4(2) . . . . ?
O1 Zn1 O2 C22 161.2(3) . . . . ?
Cl1 Zn1 O2 C22 74.8(2) . . . . ?
N2 Zn1 O2 C22 -50.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.123
_database_code_depnum_ccdc_archive 'CCDC 949746'