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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H34 N4 O4 Zn'
_chemical_formula_weight         628.02

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           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   21.494(4)
_cell_length_b                   36.481(7)
_cell_length_c                   7.2800(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5708.6(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2160
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2624
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.78
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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            6113
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2424
_reflns_number_gt                2160
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       'SMART and SAINT'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0303P)²+16.6734P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.017(17)
_refine_ls_number_reflns         2424
_refine_ls_number_parameters     195
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.077
_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
Zn1 Zn 0.5000 0.0000 0.43673(11) 0.03939(18) Uani 1 2 d SU . .
O1 O 0.42719(14) 0.01082(9) 0.1971(6) 0.0631(8) Uani 1 1 d U . .
O2 O 0.46081(14) 0.05122(7) 0.3961(5) 0.0708(11) Uani 1 1 d U . .
N1 N 0.06666(13) 0.02313(8) -0.8893(5) 0.0373(8) Uani 1 1 d . . .
C1 C 0.05516(17) 0.03489(11) -0.7201(7) 0.0483(11) Uani 1 1 d . . .
H1A H 0.0140 0.0325 -0.6740 0.058 Uiso 1 1 calc R . .
C2 C 0.09937(16) 0.05029(10) -0.6078(6) 0.0437(10) Uani 1 1 d . . .
H2A H 0.0886 0.0577 -0.4869 0.052 Uiso 1 1 calc R . .
C3 C 0.12480(15) 0.02803(9) -0.9544(5) 0.0328(8) Uani 1 1 d . . .
H3A H 0.1341 0.0202 -1.0758 0.039 Uiso 1 1 calc R . .
C4 C 0.17115(14) 0.04397(8) -0.8506(5) 0.0283(8) Uani 1 1 d . . .
H4A H 0.2113 0.0474 -0.9025 0.034 Uiso 1 1 calc R . .
C5 C 0.15983(15) 0.05499(9) -0.6715(6) 0.0313(8) Uani 1 1 d . . .
C8 C 0.28946(16) 0.05021(9) -0.3071(6) 0.0396(8) Uani 1 1 d . . .
H8A H 0.3015 0.0296 -0.2262 0.048 Uiso 1 1 calc R . .
H8B H 0.3262 0.0570 -0.3815 0.048 Uiso 1 1 calc R . .
C7 C 0.23723(17) 0.03782(9) -0.4345(6) 0.0372(9) Uani 1 1 d . . .
H7A H 0.2529 0.0181 -0.5155 0.045 Uiso 1 1 calc R . .
H7B H 0.2028 0.0276 -0.3599 0.045 Uiso 1 1 calc R . .
C6 C 0.21228(15) 0.06897(8) -0.5525(5) 0.0318(7) Uani 1 1 d . . .
H6A H 0.2466 0.0772 -0.6356 0.038 Uiso 1 1 calc R . .
C9 C 0.19552(18) 0.10085(10) -0.4285(6) 0.0434(9) Uani 1 1 d . . .
H9A H 0.1827 0.1220 -0.5051 0.052 Uiso 1 1 calc R . .
H9B H 0.1596 0.0938 -0.3507 0.052 Uiso 1 1 calc R . .
C10 C 0.2487(2) 0.11221(8) -0.3072(9) 0.0404(7) Uani 1 1 d . . .
H10A H 0.2833 0.1214 -0.3843 0.049 Uiso 1 1 calc R . .
H10B H 0.2351 0.1324 -0.2257 0.049 Uiso 1 1 calc R . .
N2 N 0.27104(13) 0.08134(7) -0.1945(4) 0.0288(6) Uani 1 1 d . . .
C11 C 0.30696(13) 0.08942(8) -0.0389(5) 0.0282(7) Uani 1 1 d . . .
C12 C 0.29750(15) 0.12184(9) 0.0623(5) 0.0319(8) Uani 1 1 d . . .
H12A H 0.2676 0.1391 0.0208 0.038 Uiso 1 1 calc R . .
C13 C 0.33030(16) 0.12899(9) 0.2185(6) 0.0374(9) Uani 1 1 d . . .
H13A H 0.3230 0.1513 0.2827 0.045 Uiso 1 1 calc R . .
C14 C 0.37425(17) 0.10437(10) 0.2862(6) 0.0419(10) Uani 1 1 d . . .
H14A H 0.3974 0.1098 0.3941 0.050 Uiso 1 1 calc R . .
C15 C 0.35054(15) 0.06418(10) 0.0325(6) 0.0333(9) Uani 1 1 d . . .
H15A H 0.3575 0.0417 -0.0299 0.040 Uiso 1 1 calc R . .
C16 C 0.38336(13) 0.07175(9) 0.1922(7) 0.0368(8) Uani 1 1 d . . .
C17 C 0.42789(17) 0.04208(13) 0.2627(6) 0.0505(11) Uani 1 1 d U . .


_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 O2 2.071(3) . ?
Zn1 O2 2.071(3) 2_655 ?
Zn1 N1 2.090(3) 9_556 ?
Zn1 N1 2.090(3) 10_556 ?
Zn1 O1 2.376(4) . ?
Zn1 O1 2.376(4) 2_655 ?
Zn1 C17 2.523(4) 2_655 ?
Zn1 C17 2.523(4) . ?
O1 C17 1.236(6) . ?
O2 C17 1.247(5) . ?
N1 C1 1.328(5) . ?
N1 C3 1.348(4) . ?
N1 Zn1 2.090(3) 9_453 ?
C1 C2 1.373(6) . ?
C1 H1A 0.9500 . ?
C2 C5 1.390(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.379(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.386(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.510(5) . ?
C8 N2 1.456(4) . ?
C8 C7 1.525(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7 C6 1.522(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 C9 1.516(5) . ?
C6 H6A 1.0000 . ?
C9 C10 1.503(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.473(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N2 C11 1.402(5) . ?
C11 C12 1.408(5) . ?
C11 C15 1.412(5) . ?
C12 C13 1.363(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.394(5) . ?
C13 H13A 0.9500 . ?
C14 C16 1.387(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.388(6) . ?
C15 H15A 0.9500 . ?
C16 C17 1.533(5) . ?

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 Zn1 O2 163.6(2) . 2_655 ?
O2 Zn1 N1 90.07(12) . 9_556 ?
O2 Zn1 N1 99.90(13) 2_655 9_556 ?
O2 Zn1 N1 99.90(13) . 10_556 ?
O2 Zn1 N1 90.07(12) 2_655 10_556 ?
N1 Zn1 N1 105.40(19) 9_556 10_556 ?
O2 Zn1 O1 58.50(12) . . ?
O2 Zn1 O1 108.24(14) 2_655 . ?
N1 Zn1 O1 146.01(13) 9_556 . ?
N1 Zn1 O1 93.47(12) 10_556 . ?
O2 Zn1 O1 108.24(14) . 2_655 ?
O2 Zn1 O1 58.50(12) 2_655 2_655 ?
N1 Zn1 O1 93.47(12) 9_556 2_655 ?
N1 Zn1 O1 146.01(13) 10_556 2_655 ?
O1 Zn1 O1 85.55(17) . 2_655 ?
O2 Zn1 C17 136.66(17) . 2_655 ?
O2 Zn1 C17 29.46(14) 2_655 2_655 ?
N1 Zn1 C17 97.40(12) 9_556 2_655 ?
N1 Zn1 C17 118.68(14) 10_556 2_655 ?
O1 Zn1 C17 97.88(14) . 2_655 ?
O1 Zn1 C17 29.04(13) 2_655 2_655 ?
O2 Zn1 C17 29.46(14) . . ?
O2 Zn1 C17 136.66(17) 2_655 . ?
N1 Zn1 C17 118.68(14) 9_556 . ?
N1 Zn1 C17 97.40(12) 10_556 . ?
O1 Zn1 C17 29.04(13) . . ?
O1 Zn1 C17 97.88(14) 2_655 . ?
C17 Zn1 C17 119.7(2) 2_655 . ?
C17 O1 Zn1 82.1(3) . . ?
C17 O2 Zn1 95.8(3) . . ?
C1 N1 C3 117.1(3) . . ?
C1 N1 Zn1 124.4(3) . 9_453 ?
C3 N1 Zn1 118.4(3) . 9_453 ?
N1 C1 C2 123.7(3) . . ?
N1 C1 H1A 118.1 . . ?
C2 C1 H1A 118.1 . . ?
C1 C2 C5 119.9(4) . . ?
C1 C2 H2A 120.0 . . ?
C5 C2 H2A 120.0 . . ?
N1 C3 C4 122.2(4) . . ?
N1 C3 H3A 118.9 . . ?
C4 C3 H3A 118.9 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C4 C5 C2 116.2(4) . . ?
C4 C5 C6 120.4(3) . . ?
C2 C5 C6 123.3(4) . . ?
N2 C8 C7 111.9(3) . . ?
N2 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C6 C7 C8 112.4(3) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C5 C6 C9 115.0(3) . . ?
C5 C6 C7 109.5(3) . . ?
C9 C6 C7 108.7(3) . . ?
C5 C6 H6A 107.8 . . ?
C9 C6 H6A 107.8 . . ?
C7 C6 H6A 107.8 . . ?
C10 C9 C6 112.4(3) . . ?
C10 C9 H9A 109.1 . . ?
C6 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C6 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
N2 C10 C9 111.4(3) . . ?
N2 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 N2 C8 118.0(3) . . ?
C11 N2 C10 117.9(3) . . ?
C8 N2 C10 111.8(3) . . ?
N2 C11 C12 121.3(3) . . ?
N2 C11 C15 121.7(3) . . ?
C12 C11 C15 116.8(3) . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12A 119.3 . . ?
C11 C12 H12A 119.3 . . ?
C12 C13 C14 121.5(3) . . ?
C12 C13 H13A 119.3 . . ?
C14 C13 H13A 119.3 . . ?
C16 C14 C13 118.3(4) . . ?
C16 C14 H14A 120.8 . . ?
C13 C14 H14A 120.8 . . ?
C16 C15 C11 121.0(3) . . ?
C16 C15 H15A 119.5 . . ?
C11 C15 H15A 119.5 . . ?
C14 C16 C15 120.8(3) . . ?
C14 C16 C17 121.9(4) . . ?
C15 C16 C17 117.2(4) . . ?
O1 C17 O2 123.7(4) . . ?
O1 C17 C16 120.9(4) . . ?
O2 C17 C16 115.2(4) . . ?
O1 C17 Zn1 68.9(3) . . ?
O2 C17 Zn1 54.8(2) . . ?
C16 C17 Zn1 168.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 838047'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H34 N4 O4 Zn'
_chemical_formula_weight         628.02

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           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   21.497(4)
_cell_length_b                   36.708(7)
_cell_length_c                   7.2655(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5733.4(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2134
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2624
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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            7106
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2541
_reflns_number_gt                2134
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       'SMART and SAINT'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0303P)²+10.2450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.010(18)
_refine_ls_number_reflns         2541
_refine_ls_number_parameters     195
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.002
_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 0.5000 0.0000 0.22430(11) 0.04481(18) Uani 1 2 d SU . .
O1 O 0.42757(15) 0.01128(10) -0.0107(6) 0.0777(9) Uani 1 1 d . . .
O2 O 0.46048(14) 0.05136(8) 0.1878(5) 0.0817(11) Uani 1 1 d U . .
C1 C 0.05418(18) 0.03496(11) -0.9329(7) 0.0580(12) Uani 1 1 d . . .
H1A H 0.0126 0.0331 -0.8892 0.070 Uiso 1 1 calc R . .
C2 C 0.09806(17) 0.04996(11) -0.8187(6) 0.0534(11) Uani 1 1 d . . .
H2A H 0.0868 0.0571 -0.6975 0.064 Uiso 1 1 calc R . .
C3 C 0.12479(16) 0.02767(9) -1.1628(5) 0.0421(8) Uani 1 1 d . . .
H3A H 0.1347 0.0198 -1.2839 0.051 Uiso 1 1 calc R . .
C4 C 0.17077(15) 0.04353(9) -1.0577(5) 0.0397(9) Uani 1 1 d . . .
H4A H 0.2111 0.0468 -1.1085 0.048 Uiso 1 1 calc R . .
C5 C 0.15902(16) 0.05477(9) -0.8794(6) 0.0381(9) Uani 1 1 d . . .
C6 C 0.21104(16) 0.06877(9) -0.7586(6) 0.0430(8) Uani 1 1 d . . .
H6A H 0.2449 0.0775 -0.8420 0.052 Uiso 1 1 calc R . .
C7 C 0.23766(18) 0.03776(10) -0.6450(6) 0.0497(10) Uani 1 1 d . . .
H7A H 0.2539 0.0187 -0.7287 0.060 Uiso 1 1 calc R . .
H7B H 0.2040 0.0268 -0.5703 0.060 Uiso 1 1 calc R . .
C8 C 0.28948(17) 0.05035(10) -0.5184(6) 0.0519(9) Uani 1 1 d . . .
H8A H 0.3024 0.0298 -0.4388 0.062 Uiso 1 1 calc R . .
H8B H 0.3258 0.0577 -0.5934 0.062 Uiso 1 1 calc R . .
C9 C 0.1939(2) 0.09996(10) -0.6343(6) 0.0574(11) Uani 1 1 d . . .
H9A H 0.1804 0.1209 -0.7104 0.069 Uiso 1 1 calc R . .
H9B H 0.1584 0.0926 -0.5559 0.069 Uiso 1 1 calc R . .
C10 C 0.2469(2) 0.11159(8) -0.5140(9) 0.0528(9) Uani 1 1 d . . .
H10A H 0.2810 0.1212 -0.5916 0.063 Uiso 1 1 calc R . .
H10B H 0.2329 0.1314 -0.4313 0.063 Uiso 1 1 calc R . .
C11 C 0.30643(14) 0.08896(8) -0.2479(5) 0.0354(8) Uani 1 1 d . . .
C12 C 0.29741(16) 0.12161(9) -0.1467(5) 0.0403(8) Uani 1 1 d . . .
H12A H 0.2679 0.1390 -0.1890 0.048 Uiso 1 1 calc R . .
C13 C 0.33010(17) 0.12855(9) 0.0099(6) 0.0464(9) Uani 1 1 d . . .
H13A H 0.3229 0.1506 0.0745 0.056 Uiso 1 1 calc R . .
C14 C 0.37372(18) 0.10408(10) 0.0772(6) 0.0506(10) Uani 1 1 d . . .
H14A H 0.3969 0.1095 0.1852 0.061 Uiso 1 1 calc R . .
C15 C 0.35028(16) 0.06420(10) -0.1760(6) 0.0414(9) Uani 1 1 d . . .
H15A H 0.3576 0.0419 -0.2389 0.050 Uiso 1 1 calc R . .
C16 C 0.38286(14) 0.07160(9) -0.0159(7) 0.0444(8) Uani 1 1 d . . .
C17 C 0.42781(19) 0.04252(15) 0.0552(7) 0.0649(14) Uani 1 1 d . . .
N1 N 0.06659(13) 0.02293(8) -1.1005(5) 0.0424(8) Uani 1 1 d . . .
N2 N 0.27048(13) 0.08098(8) -0.4027(4) 0.0364(6) 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
Zn1 O2 2.085(3) . ?
Zn1 O2 2.085(3) 2_655 ?
Zn1 N1 2.092(3) 10_556 ?
Zn1 N1 2.092(3) 9_556 ?
Zn1 O1 2.347(4) . ?
Zn1 O1 2.347(4) 2_655 ?
Zn1 C17 2.521(5) . ?
Zn1 C17 2.521(5) 2_655 ?
O1 C17 1.243(6) . ?
O2 C17 1.236(5) . ?
C1 N1 1.323(5) . ?
C1 C2 1.372(6) . ?
C1 H1A 0.9500 . ?
C2 C5 1.394(5) . ?
C2 H2A 0.9500 . ?
C3 N1 1.342(5) . ?
C3 C4 1.378(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.383(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.512(6) . ?
C6 C7 1.518(5) . ?
C6 C9 1.504(5) . ?
C6 H6A 1.0000 . ?
C7 C8 1.517(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.462(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.498(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.474(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N2 1.396(4) . ?
C11 C15 1.410(5) . ?
C11 C12 1.419(5) . ?
C12 C13 1.361(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.388(5) . ?
C13 H13A 0.9500 . ?
C14 C16 1.385(6) . ?
C14 H14A 0.9500 . ?
C15 C16 1.385(6) . ?
C15 H15A 0.9500 . ?
C16 C17 1.530(6) . ?
N1 Zn1 2.092(3) 9_453 ?

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 Zn1 O2 165.4(2) . 2_655 ?
O2 Zn1 N1 99.34(13) . 10_556 ?
O2 Zn1 N1 89.55(12) 2_655 10_556 ?
O2 Zn1 N1 89.55(12) . 9_556 ?
O2 Zn1 N1 99.34(13) 2_655 9_556 ?
N1 Zn1 N1 105.06(19) 10_556 9_556 ?
O2 Zn1 O1 58.52(13) . . ?
O2 Zn1 O1 109.72(15) 2_655 . ?
N1 Zn1 O1 93.42(12) 10_556 . ?
N1 Zn1 O1 145.61(14) 9_556 . ?
O2 Zn1 O1 109.72(15) . 2_655 ?
O2 Zn1 O1 58.52(13) 2_655 2_655 ?
N1 Zn1 O1 145.61(14) 10_556 2_655 ?
N1 Zn1 O1 93.42(12) 9_556 2_655 ?
O1 Zn1 O1 86.68(18) . 2_655 ?
O2 Zn1 C17 29.22(15) . . ?
O2 Zn1 C17 138.50(19) 2_655 . ?
N1 Zn1 C17 97.15(12) 10_556 . ?
N1 Zn1 C17 117.94(16) 9_556 . ?
O1 Zn1 C17 29.30(14) . . ?
O1 Zn1 C17 99.39(16) 2_655 . ?
O2 Zn1 C17 138.50(19) . 2_655 ?
O2 Zn1 C17 29.22(15) 2_655 2_655 ?
N1 Zn1 C17 117.94(16) 10_556 2_655 ?
N1 Zn1 C17 97.15(12) 9_556 2_655 ?
O1 Zn1 C17 99.39(16) . 2_655 ?
O1 Zn1 C17 29.30(14) 2_655 2_655 ?
C17 Zn1 C17 121.7(3) . 2_655 ?
C17 O1 Zn1 83.1(3) . . ?
C17 O2 Zn1 95.3(3) . . ?
N1 C1 C2 123.5(4) . . ?
N1 C1 H1A 118.2 . . ?
C2 C1 H1A 118.2 . . ?
C1 C2 C5 120.4(4) . . ?
C1 C2 H2A 119.8 . . ?
C5 C2 H2A 119.8 . . ?
N1 C3 C4 122.5(4) . . ?
N1 C3 H3A 118.8 . . ?
C4 C3 H3A 118.8 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C2 C5 C4 115.5(4) . . ?
C2 C5 C6 123.7(4) . . ?
C4 C5 C6 120.7(3) . . ?
C5 C6 C7 109.9(3) . . ?
C5 C6 C9 115.2(3) . . ?
C7 C6 C9 109.7(3) . . ?
C5 C6 H6A 107.2 . . ?
C7 C6 H6A 107.2 . . ?
C9 C6 H6A 107.2 . . ?
C6 C7 C8 112.2(3) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N2 C8 C7 112.2(3) . . ?
N2 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C6 112.4(3) . . ?
C10 C9 H9A 109.1 . . ?
C6 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C6 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
N2 C10 C9 111.4(3) . . ?
N2 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N2 C11 C15 122.2(3) . . ?
N2 C11 C12 121.3(3) . . ?
C15 C11 C12 116.4(3) . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H12A 119.3 . . ?
C11 C12 H12A 119.3 . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 H13A 119.3 . . ?
C14 C13 H13A 119.3 . . ?
C16 C14 C13 118.7(4) . . ?
C16 C14 H14A 120.6 . . ?
C13 C14 H14A 120.6 . . ?
C16 C15 C11 121.5(4) . . ?
C16 C15 H15A 119.2 . . ?
C11 C15 H15A 119.2 . . ?
C15 C16 C14 120.5(3) . . ?
C15 C16 C17 117.8(4) . . ?
C14 C16 C17 121.7(4) . . ?
O2 C17 O1 123.0(5) . . ?
O2 C17 C16 116.0(5) . . ?
O1 C17 C16 120.7(4) . . ?
O2 C17 Zn1 55.4(2) . . ?
O1 C17 Zn1 67.6(3) . . ?
C16 C17 Zn1 170.3(4) . . ?
C1 N1 C3 117.1(4) . . ?
C1 N1 Zn1 123.8(3) . 9_453 ?
C3 N1 Zn1 119.0(3) . 9_453 ?
C11 N2 C8 118.0(3) . . ?
C11 N2 C10 118.2(3) . . ?
C8 N2 C10 111.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 863588'
