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

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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
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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data_lvl15zn

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 N2 O5 Zn'
_chemical_formula_weight         467.76

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   6.215(2)
_cell_length_b                   20.656(8)
_cell_length_c                   25.022(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3213(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.967
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8581
_exptl_absorpt_correction_T_max  0.9253
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13374
_diffrn_reflns_av_R_equivalents  0.0921
_diffrn_reflns_av_sigmaI/netI    0.1695
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5551
_reflns_number_gt                2965
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0788P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_number_reflns         5551
_refine_ls_number_parameters     245
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0794
_refine_ls_wR_factor_ref         0.2052
_refine_ls_wR_factor_gt          0.1804
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.079
_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 0.13148(17) 0.80710(5) 1.13430(3) 0.0384(3) Uani 1 1 d . . .
N1 N 0.7534(11) 0.6053(3) 0.8552(2) 0.0375(18) Uani 1 1 d . . .
N2 N 0.9390(12) 0.5307(4) 0.8094(3) 0.046(2) Uani 1 1 d . A .
H2 H 1.0141 0.5131 0.7845 0.055 Uiso 1 1 calc R . .
O1 O 0.1559(10) 0.7430(3) 1.07543(19) 0.0375(14) Uani 1 1 d . . .
O1W O -0.1879(8) 0.8107(3) 1.15584(19) 0.0425(15) Uani 1 1 d . . .
H1WA H -0.1375 0.7829 1.1341 0.051 Uiso 1 1 d R . .
H1WB H -0.1321 0.8299 1.1292 0.051 Uiso 1 1 d R . .
O2 O 0.4837(11) 0.7723(3) 1.0952(2) 0.0553(19) Uani 1 1 d . . .
O3 O 1.5800(16) 0.2634(6) 0.7386(4) 0.149(5) Uani 1 1 d . . .
O4 O 1.2683(11) 0.2364(3) 0.7012(2) 0.0550(19) Uani 1 1 d . . .
C1 C 0.3688(19) 0.7386(4) 1.0703(3) 0.040(2) Uani 1 1 d . . .
C2 C 0.4438(13) 0.6888(4) 1.0339(3) 0.0308(19) Uani 1 1 d . . .
C3 C 0.3255(18) 0.6601(4) 0.9955(3) 0.048(3) Uani 1 1 d . . .
H3 H 0.1851 0.6745 0.9906 0.058 Uiso 1 1 calc R . .
C4 C 0.398(2) 0.6110(5) 0.9632(3) 0.074(4) Uani 1 1 d . . .
H4 H 0.3108 0.5922 0.9374 0.088 Uiso 1 1 calc R . .
C5 C 0.616(2) 0.5902(5) 0.9712(4) 0.069(4) Uani 1 1 d . . .
C6 C 0.7430(19) 0.6164(6) 1.0096(4) 0.063(3) Uani 1 1 d . . .
H6 H 0.8803 0.6005 1.0164 0.076 Uiso 1 1 calc R . .
C7 C 0.6568(17) 0.6694(4) 1.0392(3) 0.052(3) Uani 1 1 d . . .
H7 H 0.7458 0.6916 1.0628 0.063 Uiso 1 1 calc R . .
C8 C 0.700(2) 0.5378(7) 0.9390(5) 0.115(6) Uani 1 1 d . A .
C9 C 0.748(2) 0.4747(6) 0.9570(4) 0.102(3) Uani 1 1 d DU . .
C10 C 0.866(3) 0.4268(5) 0.9249(4) 0.102(3) Uani 1 1 d DU A .
C11 C 0.929(2) 0.4382(6) 0.8747(4) 0.087(4) Uani 1 1 d . . .
C12 C 0.880(3) 0.5030(6) 0.8565(4) 0.102(3) Uani 1 1 d . A .
C13 C 0.775(2) 0.5520(6) 0.8852(4) 0.102(3) Uani 1 1 d . . .
C14 C 0.615(6) 0.4453(9) 1.0084(9) 0.132(10) Uani 0.619(16) 1 d PD A 1
H14A H 0.4730 0.4328 0.9971 0.198 Uiso 0.619(16) 1 calc PR A 1
H14B H 0.6038 0.4778 1.0357 0.198 Uiso 0.619(16) 1 calc PR A 1
H14C H 0.6891 0.4082 1.0223 0.198 Uiso 0.619(16) 1 calc PR A 1
C14' C 0.783(9) 0.4708(18) 1.0229(8) 0.132(10) Uani 0.381(16) 1 d PDU A 2
H14D H 0.9246 0.4855 1.0318 0.198 Uiso 0.381(16) 1 calc PR A 2
H14E H 0.7648 0.4269 1.0346 0.198 Uiso 0.381(16) 1 calc PR A 2
H14F H 0.6781 0.4978 1.0402 0.198 Uiso 0.381(16) 1 calc PR A 2
C15 C 0.838(6) 0.3474(7) 0.9349(9) 0.132(10) Uani 0.619(16) 1 d PDU A 1
H15A H 0.7074 0.3327 0.9183 0.198 Uiso 0.619(16) 1 calc PR A 1
H15B H 0.8320 0.3387 0.9725 0.198 Uiso 0.619(16) 1 calc PR A 1
H15C H 0.9583 0.3250 0.9195 0.198 Uiso 0.619(16) 1 calc PR A 1
C15' C 1.016(6) 0.3752(17) 0.9598(12) 0.132(10) Uani 0.381(16) 1 d PD A 2
H15D H 1.1372 0.3976 0.9746 0.198 Uiso 0.381(16) 1 calc PR A 2
H15E H 1.0650 0.3411 0.9368 0.198 Uiso 0.381(16) 1 calc PR A 2
H15F H 0.9313 0.3571 0.9883 0.198 Uiso 0.381(16) 1 calc PR A 2
C16 C 0.8579(18) 0.5904(5) 0.8094(3) 0.048(2) Uani 1 1 d . . .
H16 H 0.8717 0.6189 0.7808 0.058 Uiso 1 1 calc R A .
C17 C 1.047(2) 0.3959(5) 0.8398(5) 0.074(4) Uani 1 1 d . A .
C18 C 1.248(2) 0.3775(7) 0.8516(5) 0.112(3) Uani 1 1 d . . .
H18 H 1.3135 0.3918 0.8829 0.134 Uiso 1 1 calc R A .
C19 C 1.362(3) 0.3359(6) 0.8163(5) 0.112(3) Uani 1 1 d . A .
H19 H 1.5054 0.3260 0.8236 0.134 Uiso 1 1 calc R . .
C20 C 1.2698(17) 0.3110(5) 0.7732(3) 0.053(3) Uani 1 1 d . . .
C21 C 1.060(2) 0.3220(7) 0.7641(5) 0.112(3) Uani 1 1 d . A .
H21 H 0.9863 0.2986 0.7382 0.134 Uiso 1 1 calc R . .
C22 C 0.954(2) 0.3698(7) 0.7949(5) 0.112(3) Uani 1 1 d . . .
H22 H 0.8186 0.3839 0.7845 0.134 Uiso 1 1 calc R A .
C23 C 1.389(2) 0.2649(5) 0.7347(4) 0.056(3) Uani 1 1 d . A .


_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 1.979(7) 4_467 ?
Zn1 O4 2.000(6) 2_665 ?
Zn1 O1 1.987(5) . ?
Zn1 O1W 2.058(5) . ?
N1 C13 1.339(12) . ?
N1 C16 1.353(10) . ?
N1 Zn1 1.979(7) 4_567 ?
N2 C16 1.331(11) . ?
N2 C12 1.358(12) . ?
O1 C1 1.332(12) . ?
O2 C1 1.177(11) . ?
O3 C23 1.191(13) . ?
O4 C23 1.269(12) . ?
O4 Zn1 2.000(6) 2_664 ?
C1 C2 1.451(11) . ?
C2 C3 1.347(12) . ?
C2 C7 1.390(12) . ?
C3 C4 1.374(12) . ?
C4 C5 1.431(17) . ?
C5 C6 1.359(16) . ?
C5 C8 1.446(14) . ?
C6 C7 1.425(13) . ?
C8 C9 1.414(15) . ?
C8 C13 1.456(14) . ?
C9 C10 1.469(15) . ?
C9 C14 1.645(16) . ?
C9 C14' 1.663(18) . ?
C10 C11 1.338(13) . ?
C10 C15' 1.664(19) . ?
C10 C15 1.668(15) . ?
C11 C12 1.446(15) . ?
C11 C17 1.436(14) . ?
C12 C13 1.404(14) . ?
C17 C18 1.340(16) . ?
C17 C22 1.375(16) . ?
C18 C19 1.420(15) . ?
C19 C20 1.328(14) . ?
C20 C21 1.340(16) . ?
C20 C23 1.545(14) . ?
C21 C22 1.415(16) . ?

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 O4 100.4(3) 4_467 2_665 ?
N1 Zn1 O1 132.7(3) 4_467 . ?
O4 Zn1 O1 107.3(3) 2_665 . ?
N1 Zn1 O1W 107.6(3) 4_467 . ?
O4 Zn1 O1W 95.6(2) 2_665 . ?
O1 Zn1 O1W 107.0(2) . . ?
C13 N1 C16 103.8(8) . . ?
C13 N1 Zn1 135.7(6) . 4_567 ?
C16 N1 Zn1 120.3(6) . 4_567 ?
C16 N2 C12 106.9(8) . . ?
C1 O1 Zn1 101.1(5) . . ?
C23 O4 Zn1 125.2(6) . 2_664 ?
O2 C1 O1 120.8(8) . . ?
O2 C1 C2 123.9(10) . . ?
O1 C1 C2 115.3(9) . . ?
C3 C2 C7 117.5(8) . . ?
C3 C2 C1 125.8(8) . . ?
C7 C2 C1 116.8(8) . . ?
C2 C3 C4 124.4(11) . . ?
C3 C4 C5 116.8(12) . . ?
C6 C5 C4 121.9(10) . . ?
C6 C5 C8 118.9(14) . . ?
C4 C5 C8 119.2(14) . . ?
C5 C6 C7 117.1(11) . . ?
C2 C7 C6 122.0(10) . . ?
C9 C8 C5 126.1(10) . . ?
C9 C8 C13 114.3(9) . . ?
C5 C8 C13 118.8(10) . . ?
C8 C9 C10 123.6(9) . . ?
C8 C9 C14 118.8(12) . . ?
C10 C9 C14 115.5(12) . . ?
C8 C9 C14' 112.8(16) . . ?
C10 C9 C14' 116.5(17) . . ?
C14 C9 C14' 43.4(17) . . ?
C11 C10 C9 122.8(10) . . ?
C11 C10 C15' 116.1(16) . . ?
C9 C10 C15' 115.0(15) . . ?
C11 C10 C15 110.2(11) . . ?
C9 C10 C15 121.9(12) . . ?
C15' C10 C15 49.4(15) . . ?
C10 C11 C12 113.5(10) . . ?
C10 C11 C17 127.8(11) . . ?
C12 C11 C17 118.6(9) . . ?
N2 C12 C13 105.3(10) . . ?
N2 C12 C11 127.4(10) . . ?
C13 C12 C11 127.2(10) . . ?
N1 C13 C12 110.7(9) . . ?
N1 C13 C8 130.6(10) . . ?
C12 C13 C8 118.6(11) . . ?
N2 C16 N1 113.1(8) . . ?
C18 C17 C22 117.4(12) . . ?
C18 C17 C11 121.1(13) . . ?
C22 C17 C11 121.4(12) . . ?
C17 C18 C19 120.1(13) . . ?
C20 C19 C18 121.5(14) . . ?
C19 C20 C21 119.5(12) . . ?
C19 C20 C23 122.5(11) . . ?
C21 C20 C23 117.8(10) . . ?
C20 C21 C22 118.6(13) . . ?
C17 C22 C21 121.6(13) . . ?
O3 C23 O4 129.2(10) . . ?
O3 C23 C20 116.4(10) . . ?
O4 C23 C20 114.4(10) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.092
_database_code_depnum_ccdc_archive 'CCDC 963443'
