# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1515067'
_audit_update_record             
;
2016-11-04 deposited with the CCDC.
2016-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N1.50 O4 Zn'
_chemical_formula_weight         341.62

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.9154(2)
_cell_length_b                   21.9224(6)
_cell_length_c                   9.5537(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.7430(10)
_cell_angle_gamma                90.00
_cell_volume                     1354.48(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5544
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.43

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             694
_exptl_absorpt_coefficient_mu    1.831
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7110
_exptl_absorpt_correction_T_max  0.7341
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_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            9612
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2396
_reflns_number_gt                2214
_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    'Bruker SHELXTL'
_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)+(0.0362P)²+1.1819P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refu
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2396
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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 0.0601(5) 0.26162(12) 0.1611(3) 0.0404(6) Uani 1 1 d . . .
C2 C 0.3282(5) 0.37835(13) -0.0162(3) 0.0427(7) Uani 1 1 d . . .
C3 C 0.4215(4) 0.44072(12) -0.0075(3) 0.0361(6) Uani 1 1 d . . .
C4 C 0.2945(4) 0.49089(13) -0.0237(3) 0.0397(6) Uani 1 1 d . . .
H4 H 0.1552 0.4847 -0.0401 0.048 Uiso 1 1 calc R . .
C5 C 0.3676(4) 0.55042(12) -0.0165(3) 0.0392(6) Uani 1 1 d . . .
C6 C 0.6092(4) 0.16558(12) 0.1217(3) 0.0407(6) Uani 1 1 d . . .
H6 H 0.5556 0.1705 0.1976 0.049 Uiso 1 1 calc R . .
C7 C 0.7808(4) 0.12926(13) 0.1491(3) 0.0406(6) Uani 1 1 d . . .
H7 H 0.8421 0.1111 0.2423 0.049 Uiso 1 1 calc R . .
C8 C 0.8625(4) 0.11969(11) 0.0373(3) 0.0355(6) Uani 1 1 d . . .
C9 C 0.7609(4) 0.14819(13) -0.0993(3) 0.0421(6) Uani 1 1 d . . .
H9 H 0.8068 0.1425 -0.1788 0.051 Uiso 1 1 calc R . .
C10 C 0.5939(4) 0.18443(13) -0.1162(3) 0.0451(7) Uani 1 1 d . . .
H10 H 0.5304 0.2036 -0.2080 0.054 Uiso 1 1 calc R . .
C11 C 1.0474(4) 0.08213(13) 0.0646(3) 0.0399(6) Uani 1 1 d . . .
C12 C 1.1403(4) 0.07262(13) -0.0329(3) 0.0402(6) Uani 1 1 d . . .
C13 C 1.3951(4) 0.02930(13) -0.1315(3) 0.0400(6) Uani 1 1 d . . .
H13 H 1.3241 0.0489 -0.2214 0.048 Uiso 1 1 calc R . .
C14 C 1.3240(4) 0.03515(12) -0.0127(3) 0.0355(6) Uani 1 1 d . . .
C15 C 1.4329(4) 0.00462(13) 0.1194(3) 0.0395(6) Uani 1 1 d . . .
H15 H 1.3886 0.0072 0.2005 0.047 Uiso 1 1 calc R . .
H1M H -0.066(5) 0.2751(14) 0.075(3) 0.048(8) Uiso 1 1 d . . .
H2M H 1.081(5) 0.0911(15) -0.133(4) 0.055(9) Uiso 1 1 d . . .
H3M H 1.099(5) 0.0622(14) 0.160(3) 0.049(8) Uiso 1 1 d . . .
N1 N 0.5157(3) 0.19409(9) -0.0078(3) 0.0365(5) Uani 1 1 d . . .
N3 N 0.2328(8) 0.5963(2) -0.0376(6) 0.0533(13) Uani 0.50 1 d P . .
H3A H 0.1043 0.5887 -0.0552 0.064 Uiso 0.50 1 calc PR . .
H3B H 0.2745 0.6334 -0.0336 0.064 Uiso 0.50 1 calc PR . .
O1 O 0.0430(3) 0.26534(9) 0.2861(2) 0.0451(5) Uani 1 1 d . . .
O2 O 0.2169(3) 0.24236(8) 0.1399(2) 0.0394(4) Uani 1 1 d . . .
O3 O 0.4397(4) 0.33350(9) -0.0259(3) 0.0550(5) Uani 1 1 d . . .
O4 O 0.1525(4) 0.37232(10) -0.0136(3) 0.0644(6) Uani 1 1 d . . .
Zn1 Zn 0.28758(5) 0.257104(13) -0.04101(3) 0.03560(13) 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 O1 1.243(3) . ?
C1 O2 1.245(3) . ?
C1 H1M 1.01(3) . ?
C2 O4 1.231(4) . ?
C2 O3 1.273(4) . ?
C2 C3 1.502(4) . ?
C3 C4 1.381(4) . ?
C3 C5 1.407(4) 3_665 ?
C4 C5 1.392(4) . ?
C4 H4 0.9300 . ?
C5 N3 1.338(6) . ?
C5 C3 1.407(4) 3_665 ?
C6 N1 1.332(3) . ?
C6 C7 1.375(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(4) . ?
C8 C11 1.465(4) . ?
C9 C10 1.363(4) . ?
C9 H9 0.9300 . ?
C10 N1 1.344(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.322(4) . ?
C11 H3M 0.96(3) . ?
C12 C14 1.467(4) . ?
C12 H2M 0.99(3) . ?
C13 C15 1.373(4) 3_855 ?
C13 C14 1.393(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(4) . ?
C15 C13 1.373(4) 3_855 ?
C15 H15 0.9300 . ?
N1 Zn1 2.036(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
O1 Zn1 1.9628(19) 4_566 ?
O2 Zn1 1.9824(19) . ?
O3 Zn1 1.956(2) . ?
Zn1 O1 1.9628(19) 4_565 ?

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 C1 O2 124.2(3) . . ?
O1 C1 H1M 114.5(17) . . ?
O2 C1 H1M 121.2(17) . . ?
O4 C2 O3 123.1(3) . . ?
O4 C2 C3 120.3(3) . . ?
O3 C2 C3 116.6(3) . . ?
C4 C3 C5 119.3(2) . 3_665 ?
C4 C3 C2 118.4(2) . . ?
C5 C3 C2 122.3(2) 3_665 . ?
C3 C4 C5 122.4(2) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
N3 C5 C4 118.4(3) . . ?
N3 C5 C3 123.2(3) . 3_665 ?
C4 C5 C3 118.3(3) . 3_665 ?
N1 C6 C7 123.4(3) . . ?
N1 C6 H6 118.3 . . ?
C7 C6 H6 118.3 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 116.4(2) . . ?
C7 C8 C11 121.0(2) . . ?
C9 C8 C11 122.5(2) . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N1 C10 C9 123.7(3) . . ?
N1 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C12 C11 C8 125.1(3) . . ?
C12 C11 H3M 119.0(18) . . ?
C8 C11 H3M 115.9(18) . . ?
C11 C12 C14 127.6(3) . . ?
C11 C12 H2M 119.0(18) . . ?
C14 C12 H2M 113.4(18) . . ?
C15 C13 C14 121.8(2) 3_855 . ?
C15 C13 H13 119.1 3_855 . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 117.5(2) . . ?
C15 C14 C12 123.6(2) . . ?
C13 C14 C12 118.9(2) . . ?
C13 C15 C14 120.7(2) 3_855 . ?
C13 C15 H15 119.6 3_855 . ?
C14 C15 H15 119.6 . . ?
C6 N1 C10 116.6(2) . . ?
C6 N1 Zn1 123.91(18) . . ?
C10 N1 Zn1 119.18(18) . . ?
C5 N3 H3A 120.0 . . ?
C5 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C1 O1 Zn1 116.43(18) . 4_566 ?
C1 O2 Zn1 125.74(18) . . ?
C2 O3 Zn1 110.04(19) . . ?
O3 Zn1 O1 123.88(9) . 4_565 ?
O3 Zn1 O2 111.57(9) . . ?
O1 Zn1 O2 106.75(8) 4_565 . ?
O3 Zn1 N1 101.69(9) . . ?
O1 Zn1 N1 110.51(9) 4_565 . ?
O2 Zn1 N1 99.80(8) . . ?

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
O4 C2 C3 C4 -11.5(4) . . . . ?
O3 C2 C3 C4 168.6(2) . . . . ?
O4 C2 C3 C5 168.5(3) . . . 3_665 ?
O3 C2 C3 C5 -11.4(4) . . . 3_665 ?
C5 C3 C4 C5 -0.3(4) 3_665 . . . ?
C2 C3 C4 C5 179.6(2) . . . . ?
C3 C4 C5 N3 178.1(3) . . . . ?
C3 C4 C5 C3 0.3(4) . . . 3_665 ?
N1 C6 C7 C8 -1.5(4) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C6 C7 C8 C11 178.8(3) . . . . ?
C7 C8 C9 C10 1.6(4) . . . . ?
C11 C8 C9 C10 -177.6(3) . . . . ?
C8 C9 C10 N1 -1.2(5) . . . . ?
C7 C8 C11 C12 -177.1(3) . . . . ?
C9 C8 C11 C12 2.0(4) . . . . ?
C8 C11 C12 C14 -179.4(3) . . . . ?
C15 C13 C14 C15 -0.7(4) 3_855 . . . ?
C15 C13 C14 C12 179.4(3) 3_855 . . . ?
C11 C12 C14 C15 -1.9(5) . . . . ?
C11 C12 C14 C13 178.0(3) . . . . ?
C13 C14 C15 C13 0.7(4) . . . 3_855 ?
C12 C14 C15 C13 -179.4(3) . . . 3_855 ?
C7 C6 N1 C10 1.9(4) . . . . ?
C7 C6 N1 Zn1 -171.1(2) . . . . ?
C9 C10 N1 C6 -0.6(4) . . . . ?
C9 C10 N1 Zn1 172.8(2) . . . . ?
O2 C1 O1 Zn1 3.2(4) . . . 4_566 ?
O1 C1 O2 Zn1 -161.0(2) . . . . ?
O4 C2 O3 Zn1 1.5(4) . . . . ?
C3 C2 O3 Zn1 -178.58(17) . . . . ?
C2 O3 Zn1 O1 67.4(2) . . . 4_565 ?
C2 O3 Zn1 O2 -62.3(2) . . . . ?
C2 O3 Zn1 N1 -167.86(19) . . . . ?
C1 O2 Zn1 O3 86.9(2) . . . . ?
C1 O2 Zn1 O1 -51.2(2) . . . 4_565 ?
C1 O2 Zn1 N1 -166.2(2) . . . . ?
C6 N1 Zn1 O3 100.6(2) . . . . ?
C10 N1 Zn1 O3 -72.3(2) . . . . ?
C6 N1 Zn1 O1 -126.2(2) . . . 4_565 ?
C10 N1 Zn1 O1 60.9(2) . . . 4_565 ?
C6 N1 Zn1 O2 -14.0(2) . . . . ?
C10 N1 Zn1 O2 173.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.060
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zl2015091301_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1515068'
_audit_update_record             
;
2016-11-04 deposited with the CCDC.
2016-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N1.50 O4 Zn'
_chemical_formula_weight         341.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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   P2(1)/c

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

_cell_length_a                   7.2678(8)
_cell_length_b                   21.715(2)
_cell_length_c                   9.4795(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.248(6)
_cell_angle_gamma                90.00
_cell_volume                     1394.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2616
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      21.62

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             694
_exptl_absorpt_coefficient_mu    1.778
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7175
_exptl_absorpt_correction_T_max  0.7402
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_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            8233
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2451
_reflns_number_gt                1793
_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    'Bruker SHELXTL'
_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)+(0.0481P)²+14.5133P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refu
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2451
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0869
_refine_ls_wR_factor_ref         0.2169
_refine_ls_wR_factor_gt          0.2053
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_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
C1 C 1.3518(16) 0.2610(5) 0.3510(12) 0.054(3) Uani 1 1 d . . .
H1 H 1.4605 0.2692 0.4381 0.065 Uiso 1 1 calc R . .
C2 C 1.130(2) 0.3737(5) 0.5307(10) 0.056(3) Uani 1 1 d . . .
C3 C 0.8609(17) 0.4530(4) 0.4896(9) 0.050(3) Uani 1 1 d . . .
C4 C 1.1912(17) 0.4845(5) 0.5264(9) 0.052(3) Uani 1 1 d . . .
H4 H 1.3222 0.4738 0.5465 0.063 Uiso 1 1 calc R . .
C5 C 0.8267(17) 0.1788(5) 0.6162(12) 0.060(3) Uani 1 1 d . . .
H5 H 0.8705 0.2008 0.7065 0.072 Uiso 1 1 calc R . .
C6 C 0.6819(15) 0.1347(5) 0.5951(12) 0.056(3) Uani 1 1 d . . .
H6 H 0.6303 0.1278 0.6703 0.067 Uiso 1 1 calc R . .
C7 C 0.6137(13) 0.1011(5) 0.4630(10) 0.046(2) Uani 1 1 d . . .
C8 C 0.6890(14) 0.1169(5) 0.3509(10) 0.050(3) Uani 1 1 d . . .
H8 H 0.6402 0.0978 0.2567 0.060 Uiso 1 1 calc R . .
C9 C 0.8331(15) 0.1600(4) 0.3799(11) 0.049(2) Uani 1 1 d . . .
H9 H 0.8835 0.1685 0.3048 0.058 Uiso 1 1 calc R . .
C10 C 0.4828(14) 0.0442(5) 0.4363(11) 0.052(3) Uani 1 1 d . . .
C11 C 0.4106(13) 0.0204(5) 0.5612(10) 0.046(2) Uani 1 1 d . . .
C12 C 0.1944(12) 0.0158(5) 0.5266(9) 0.041(2) Uani 1 1 d . . .
C13 C 0.0698(13) -0.0061(4) 0.3842(9) 0.042(2) Uani 1 1 d . . .
H13 H 0.1178 -0.0106 0.3061 0.050 Uiso 1 1 calc R . .
C14 C 0.1212(13) 0.0206(4) 0.6389(9) 0.040(2) Uani 1 1 d . . .
H14 H 0.2034 0.0341 0.7340 0.048 Uiso 1 1 calc R . .
C15 C 1.0573(17) 0.4388(4) 0.5136(9) 0.049(3) Uani 1 1 d . . .
H1M H 0.363(15) 0.059(5) 0.341(12) 0.07(3) Uiso 1 1 d . . .
H2M H 0.478(12) 0.048(4) 0.670(10) 0.04(2) Uiso 1 1 d . . .
N1 N 0.708(3) 0.4089(9) 0.475(2) 0.071(5) Uani 0.50 1 d P . .
H1A H 0.7350 0.3701 0.4812 0.086 Uiso 0.50 1 calc PR . .
H1B H 0.5903 0.4211 0.4605 0.086 Uiso 0.50 1 calc PR . .
N2 N 0.9072(12) 0.1912(3) 0.5116(9) 0.048(2) Uani 1 1 d . . .
O1 O 1.1992(11) 0.2404(3) 0.3655(7) 0.0523(17) Uani 1 1 d . . .
O2 O 1.3662(11) 0.2711(3) 0.2282(8) 0.0599(19) Uani 1 1 d . . .
O3 O 1.0067(14) 0.3318(3) 0.5313(8) 0.072(2) Uani 1 1 d . . .
O4 O 1.3006(14) 0.3623(4) 0.5484(11) 0.091(3) Uani 1 1 d . . .
Zn1 Zn 1.13385(18) 0.25216(5) 0.55151(13) 0.0457(4) 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 O2 1.225(12) . ?
C1 O1 1.249(12) . ?
C1 H1 0.9300 . ?
C2 O4 1.218(14) . ?
C2 O3 1.277(14) . ?
C2 C15 1.496(13) . ?
C3 C15 1.396(15) . ?
C3 C4 1.402(13) 3_766 ?
C3 N1 1.43(2) . ?
C4 C15 1.365(15) . ?
C4 C3 1.402(13) 3_766 ?
C4 H4 0.9300 . ?
C5 N2 1.349(12) . ?
C5 C6 1.382(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(14) . ?
C6 H6 0.9300 . ?
C7 C8 1.403(12) . ?
C7 C10 1.523(14) . ?
C8 C9 1.356(13) . ?
C8 H8 0.9300 . ?
C9 N2 1.349(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.548(12) . ?
C10 C11 1.599(15) 3_656 ?
C10 H1M 1.05(11) . ?
C11 C12 1.488(12) . ?
C11 C10 1.599(15) 3_656 ?
C11 H2M 1.15(9) . ?
C12 C14 1.355(11) . ?
C12 C13 1.408(11) . ?
C13 C14 1.362(12) 3_556 ?
C13 H13 0.9300 . ?
C14 C13 1.362(12) 3_556 ?
C14 H14 0.9300 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 Zn1 2.039(8) . ?
O1 Zn1 2.002(6) . ?
O2 Zn1 1.965(7) 4_565 ?
O3 Zn1 1.936(7) . ?
Zn1 O2 1.965(7) 4_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 123.6(9) . . ?
O2 C1 H1 118.2 . . ?
O1 C1 H1 118.2 . . ?
O4 C2 O3 122.2(10) . . ?
O4 C2 C15 120.6(12) . . ?
O3 C2 C15 117.2(11) . . ?
C15 C3 C4 116.8(10) . 3_766 ?
C15 C3 N1 125.3(12) . . ?
C4 C3 N1 117.9(13) 3_766 . ?
C15 C4 C3 122.6(10) . 3_766 ?
C15 C4 H4 118.7 . . ?
C3 C4 H4 118.7 3_766 . ?
N2 C5 C6 122.8(10) . . ?
N2 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C7 C6 C5 120.2(9) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 116.6(9) . . ?
C6 C7 C10 125.3(8) . . ?
C8 C7 C10 117.7(9) . . ?
C9 C8 C7 120.0(9) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
N2 C9 C8 123.6(9) . . ?
N2 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
C7 C10 C11 120.6(9) . . ?
C7 C10 C11 116.0(8) . 3_656 ?
C11 C10 C11 89.5(7) . 3_656 ?
C7 C10 H1M 100(6) . . ?
C11 C10 H1M 111(6) . . ?
C11 C10 H1M 122(6) 3_656 . ?
C12 C11 C10 118.5(8) . . ?
C12 C11 C10 114.3(8) . 3_656 ?
C10 C11 C10 90.5(7) . 3_656 ?
C12 C11 H2M 108(4) . . ?
C10 C11 H2M 111(4) . . ?
C10 C11 H2M 114(4) 3_656 . ?
C14 C12 C13 118.7(8) . . ?
C14 C12 C11 120.3(8) . . ?
C13 C12 C11 119.7(8) . . ?
C14 C13 C12 119.7(8) 3_556 . ?
C14 C13 H13 120.1 3_556 . ?
C12 C13 H13 120.1 . . ?
C12 C14 C13 121.5(8) . 3_556 ?
C12 C14 H14 119.2 . . ?
C13 C14 H14 119.2 3_556 . ?
C4 C15 C3 120.6(9) . . ?
C4 C15 C2 117.8(11) . . ?
C3 C15 C2 121.6(10) . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C9 N2 C5 116.5(8) . . ?
C9 N2 Zn1 121.5(6) . . ?
C5 N2 Zn1 122.0(7) . . ?
C1 O1 Zn1 123.7(6) . . ?
C1 O2 Zn1 114.9(7) . 4_565 ?
C2 O3 Zn1 109.2(8) . . ?
O3 Zn1 O2 123.1(3) . 4_566 ?
O3 Zn1 O1 106.5(3) . . ?
O2 Zn1 O1 108.3(3) 4_566 . ?
O3 Zn1 N2 103.7(4) . . ?
O2 Zn1 N2 112.2(3) 4_566 . ?
O1 Zn1 N2 100.8(3) . . ?

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
N2 C5 C6 C7 0.2(17) . . . . ?
C5 C6 C7 C8 -4.1(15) . . . . ?
C5 C6 C7 C10 168.7(10) . . . . ?
C6 C7 C8 C9 5.1(15) . . . . ?
C10 C7 C8 C9 -168.3(9) . . . . ?
C7 C8 C9 N2 -2.2(16) . . . . ?
C6 C7 C10 C11 1.5(16) . . . . ?
C8 C7 C10 C11 174.2(9) . . . . ?
C6 C7 C10 C11 -104.7(12) . . . 3_656 ?
C8 C7 C10 C11 68.0(11) . . . 3_656 ?
C7 C10 C11 C12 121.5(10) . . . . ?
C11 C10 C11 C12 -118.2(10) 3_656 . . . ?
C7 C10 C11 C10 -120.3(11) . . . 3_656 ?
C11 C10 C11 C10 0.0 3_656 . . 3_656 ?
C10 C11 C12 C14 -152.4(10) . . . . ?
C10 C11 C12 C14 102.8(11) 3_656 . . . ?
C10 C11 C12 C13 40.7(14) . . . . ?
C10 C11 C12 C13 -64.1(11) 3_656 . . . ?
C14 C12 C13 C14 1.4(16) . . . 3_556 ?
C11 C12 C13 C14 168.5(9) . . . 3_556 ?
C13 C12 C14 C13 -1.4(16) . . . 3_556 ?
C11 C12 C14 C13 -168.4(9) . . . 3_556 ?
C3 C4 C15 C3 -2.6(14) 3_766 . . . ?
C3 C4 C15 C2 179.2(8) 3_766 . . . ?
C4 C3 C15 C4 2.5(14) 3_766 . . . ?
N1 C3 C15 C4 -179.7(11) . . . . ?
C4 C3 C15 C2 -179.4(7) 3_766 . . . ?
N1 C3 C15 C2 -1.6(15) . . . . ?
O4 C2 C15 C4 -3.3(13) . . . . ?
O3 C2 C15 C4 174.2(8) . . . . ?
O4 C2 C15 C3 178.5(9) . . . . ?
O3 C2 C15 C3 -4.0(13) . . . . ?
C8 C9 N2 C5 -1.7(15) . . . . ?
C8 C9 N2 Zn1 176.7(8) . . . . ?
C6 C5 N2 C9 2.8(15) . . . . ?
C6 C5 N2 Zn1 -175.7(8) . . . . ?
O2 C1 O1 Zn1 -156.7(8) . . . . ?
O1 C1 O2 Zn1 -3.3(13) . . . 4_565 ?
O4 C2 O3 Zn1 -3.4(12) . . . . ?
C15 C2 O3 Zn1 179.1(6) . . . . ?
C2 O3 Zn1 O2 61.5(7) . . . 4_566 ?
C2 O3 Zn1 O1 -64.1(7) . . . . ?
C2 O3 Zn1 N2 -170.0(6) . . . . ?
C1 O1 Zn1 O3 84.5(8) . . . . ?
C1 O1 Zn1 O2 -49.7(8) . . . 4_566 ?
C1 O1 Zn1 N2 -167.6(8) . . . . ?
C9 N2 Zn1 O3 105.1(7) . . . . ?
C5 N2 Zn1 O3 -76.5(8) . . . . ?
C9 N2 Zn1 O2 -119.9(7) . . . 4_566 ?
C5 N2 Zn1 O2 58.5(8) . . . 4_566 ?
C9 N2 Zn1 O1 -4.9(8) . . . . ?
C5 N2 Zn1 O1 173.5(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.672
_refine_diff_density_min         -1.575
_refine_diff_density_rms         0.128
