# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_2-bpe

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 N2 O6 Zn'
_chemical_formula_sum            'C25 H17 N2 O6 Zn'
_chemical_formula_weight         506.78

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/n

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

_cell_length_a                   18.085(6)
_cell_length_b                   9.034(3)
_cell_length_c                   22.337(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.725(4)
_cell_angle_gamma                90.00
_cell_volume                     3586(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8371
_cell_measurement_theta_min      2.2542
_cell_measurement_theta_max      27.4835

_exptl_crystal_description       Bulk
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.939
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1036
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6186
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  Multi-scan
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27597
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.42
_reflns_number_total             8155
_reflns_number_gt                6234
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_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)+(0.1108P)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     SHELXL
_refine_ls_extinction_coef       0.0042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8155
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1778
_refine_ls_wR_factor_gt          0.1687
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.490288(16) 0.49184(3) 0.636905(11) 0.03888(13) Uani 1 1 d . . .
O1 O 0.52263(11) 0.31636(19) 0.40511(8) 0.0491(4) Uani 1 1 d . . .
O2 O 0.41387(11) 0.3490(2) 0.43589(8) 0.0502(4) Uani 1 1 d . . .
O3 O 0.48042(12) 0.3530(2) 0.56988(8) 0.0520(5) Uani 1 1 d . . .
O4 O 0.38303(15) 0.2218(3) 0.58590(12) 0.0820(7) Uani 1 1 d . . .
O5 O 0.45140(18) 0.7335(4) 1.29590(13) 0.1077(10) Uani 1 1 d . . .
O6 O 0.41679(16) 0.5020(3) 1.29810(12) 0.0835(9) Uani 1 1 d . . .
N1 N 0.41443(15) 0.5147(2) 0.69424(10) 0.0485(5) Uani 1 1 d . . .
N2 N 0.17730(12) 0.7246(3) 1.02105(8) 0.0474(5) Uani 1 1 d . . .
C1 C 0.47264(14) 0.2794(3) 0.43545(9) 0.0396(5) Uani 1 1 d . . .
C2 C 0.48796(13) 0.1377(2) 0.47068(9) 0.0354(5) Uani 1 1 d . . .
C3 C 0.46681(13) 0.1148(3) 0.52732(9) 0.0366(5) Uani 1 1 d . . .
C4 C 0.43892(15) 0.2392(3) 0.56304(10) 0.0428(5) Uani 1 1 d . . .
C5 C 0.47826(14) -0.0204(2) 0.55526(11) 0.0389(5) Uani 1 1 d . . .
H1 H 0.4629 -0.0351 0.5932 0.047 Uiso 1 1 calc R . .
C6 C 0.40263(19) 0.6492(4) 0.71498(13) 0.0593(7) Uani 1 1 d . . .
H2 H 0.4207 0.7328 0.6963 0.071 Uiso 1 1 calc R . .
C7 C 0.3648(2) 0.6716(4) 0.76295(15) 0.0732(9) Uani 1 1 d . . .
H3 H 0.3566 0.7689 0.7765 0.088 Uiso 1 1 calc R . .
C8 C 0.3387(2) 0.5476(5) 0.79114(13) 0.0661(8) Uani 1 1 d . . .
C9 C 0.3499(2) 0.4125(4) 0.76836(15) 0.0703(9) Uani 1 1 d . . .
H4 H 0.3319 0.3266 0.7856 0.084 Uiso 1 1 calc R . .
C10 C 0.38723(19) 0.3990(4) 0.72055(14) 0.0614(8) Uani 1 1 d . . .
H5 H 0.3941 0.3027 0.7054 0.074 Uiso 1 1 calc R . .
C11 C 0.2984(2) 0.5556(5) 0.84334(15) 0.0728(9) Uani 1 1 d . . .
H7 H 0.2868 0.4654 0.8614 0.087 Uiso 1 1 calc R . .
C12 C 0.2779(2) 0.6798(4) 0.86577(15) 0.0752(9) Uani 1 1 d . . .
H6 H 0.2887 0.7695 0.8470 0.090 Uiso 1 1 calc R . .
C13 C 0.23921(18) 0.6896(4) 0.91848(13) 0.0615(8) Uani 1 1 d . . .
C14 C 0.2370(2) 0.8246(4) 0.94588(14) 0.0702(9) Uani 1 1 d . . .
H8 H 0.2561 0.9093 0.9287 0.084 Uiso 1 1 calc R . .
C15 C 0.20786(19) 0.8388(3) 0.99722(13) 0.0609(7) Uani 1 1 d . . .
H11 H 0.2093 0.9327 1.0166 0.073 Uiso 1 1 calc R . .
C16 C 0.17300(16) 0.5918(4) 0.99364(12) 0.0564(7) Uani 1 1 d . . .
H10 H 0.1483 0.5118 1.0093 0.068 Uiso 1 1 calc R . .
C17 C 0.20437(19) 0.5722(4) 0.94304(13) 0.0642(8) Uani 1 1 d . . .
H9 H 0.2025 0.4774 0.9243 0.077 Uiso 1 1 calc R . .
C18 C 0.15419(16) 0.7407(4) 1.08106(10) 0.0602(8) Uani 1 1 d . . .
H13 H 0.1121 0.6722 1.0836 0.072 Uiso 1 1 calc R . .
H12 H 0.1367 0.8431 1.0859 0.072 Uiso 1 1 calc R . .
C19 C 0.22047(15) 0.7057(4) 1.13123(11) 0.0527(7) Uani 1 1 d . . .
C20 C 0.2633(2) 0.8234(5) 1.16072(14) 0.0784(10) Uani 1 1 d . . .
H14 H 0.2506 0.9225 1.1489 0.094 Uiso 1 1 calc R . .
C21 C 0.3241(2) 0.7946(5) 1.20706(16) 0.0842(11) Uani 1 1 d . . .
H15 H 0.3528 0.8746 1.2271 0.101 Uiso 1 1 calc R . .
C22 C 0.34287(18) 0.6554(4) 1.22384(12) 0.0653(9) Uani 1 1 d . . .
C23 C 0.3007(2) 0.5366(5) 1.19482(17) 0.0802(11) Uani 1 1 d . . .
H17 H 0.3135 0.4376 1.2068 0.096 Uiso 1 1 calc R . .
C24 C 0.2395(2) 0.5657(5) 1.14792(14) 0.0727(9) Uani 1 1 d . . .
H16 H 0.2112 0.4858 1.1277 0.087 Uiso 1 1 calc R . .
C25 C 0.4082(2) 0.6283(6) 1.27686(16) 0.0810(11) 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 O3 1.9356(18) . ?
Zn1 O1 1.9638(17) 3_666 ?
Zn1 O6 2.007(3) 3_667 ?
Zn1 N1 2.054(2) . ?
O1 C1 1.271(3) . ?
O1 Zn1 1.9638(17) 3_666 ?
O2 C1 1.236(3) . ?
O3 C4 1.265(3) . ?
O4 C4 1.224(3) . ?
O5 C25 1.253(5) . ?
O6 C25 1.234(5) . ?
O6 Zn1 2.007(3) 3_667 ?
N1 C6 1.332(4) . ?
N1 C10 1.337(4) . ?
N2 C15 1.328(4) . ?
N2 C16 1.343(4) . ?
N2 C18 1.483(3) . ?
C1 C2 1.501(3) . ?
C2 C5 1.401(3) 3_656 ?
C2 C3 1.404(3) . ?
C3 C5 1.370(3) . ?
C3 C4 1.518(3) . ?
C5 C2 1.401(3) 3_656 ?
C6 C7 1.390(4) . ?
C7 C8 1.409(5) . ?
C8 C9 1.352(5) . ?
C8 C11 1.488(4) . ?
C9 C10 1.371(4) . ?
C11 C12 1.310(5) . ?
C12 C13 1.480(4) . ?
C13 C14 1.369(5) . ?
C13 C17 1.397(5) . ?
C14 C15 1.354(4) . ?
C16 C17 1.367(4) . ?
C18 C19 1.514(4) . ?
C19 C24 1.345(5) . ?
C19 C20 1.405(5) . ?
C20 C21 1.388(5) . ?
C21 C22 1.338(5) . ?
C22 C23 1.404(6) . ?
C22 C25 1.529(5) . ?
C23 C24 1.400(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
O3 Zn1 O1 102.50(8) . 3_666 ?
O3 Zn1 O6 121.45(11) . 3_667 ?
O1 Zn1 O6 109.30(10) 3_666 3_667 ?
O3 Zn1 N1 124.84(9) . . ?
O1 Zn1 N1 100.11(8) 3_666 . ?
O6 Zn1 N1 96.47(11) 3_667 . ?
C1 O1 Zn1 116.95(16) . 3_666 ?
C4 O3 Zn1 125.95(16) . . ?
C25 O6 Zn1 106.3(3) . 3_667 ?
C6 N1 C10 117.7(3) . . ?
C6 N1 Zn1 118.53(19) . . ?
C10 N1 Zn1 122.6(2) . . ?
C15 N2 C16 120.3(2) . . ?
C15 N2 C18 119.7(3) . . ?
C16 N2 C18 119.8(2) . . ?
O2 C1 O1 124.6(2) . . ?
O2 C1 C2 120.3(2) . . ?
O1 C1 C2 115.0(2) . . ?
C5 C2 C3 118.3(2) 3_656 . ?
C5 C2 C1 118.71(19) 3_656 . ?
C3 C2 C1 122.93(19) . . ?
C5 C3 C2 119.9(2) . . ?
C5 C3 C4 117.2(2) . . ?
C2 C3 C4 122.5(2) . . ?
O4 C4 O3 124.8(2) . . ?
O4 C4 C3 120.3(2) . . ?
O3 C4 C3 114.7(2) . . ?
C3 C5 C2 121.8(2) . 3_656 ?
N1 C6 C7 122.4(3) . . ?
C6 C7 C8 118.9(3) . . ?
C9 C8 C7 117.6(3) . . ?
C9 C8 C11 117.9(3) . . ?
C7 C8 C11 124.5(3) . . ?
C8 C9 C10 120.3(3) . . ?
N1 C10 C9 123.2(3) . . ?
C12 C11 C8 123.8(4) . . ?
C11 C12 C13 124.4(4) . . ?
C14 C13 C17 116.6(3) . . ?
C14 C13 C12 117.8(3) . . ?
C17 C13 C12 125.6(3) . . ?
C15 C14 C13 120.8(3) . . ?
N2 C15 C14 121.5(3) . . ?
N2 C16 C17 119.7(3) . . ?
C16 C17 C13 120.9(3) . . ?
N2 C18 C19 109.3(2) . . ?
C24 C19 C20 119.4(3) . . ?
C24 C19 C18 121.9(3) . . ?
C20 C19 C18 118.7(3) . . ?
C21 C20 C19 120.0(4) . . ?
C22 C21 C20 120.6(4) . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 C25 119.1(4) . . ?
C23 C22 C25 120.7(4) . . ?
C24 C23 C22 119.2(4) . . ?
C19 C24 C23 120.7(4) . . ?
O6 C25 O5 123.0(4) . . ?
O6 C25 C22 118.0(4) . . ?
O5 C25 C22 119.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.42
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.081
# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.077 -0.025 0.282 1733.1 372.8
_platon_squeeze_details          
; ?
;
_database_code_depnum_ccdc_archive 'CCDC 989779'
#######################################################################
#
#                 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-bpy

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 N2 O6 Zn'
_chemical_formula_sum            'C23 H15 N2 O6 Zn'
_chemical_formula_weight         480.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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/n

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

_cell_length_a                   16.2561(6)
_cell_length_b                   9.0343(2)
_cell_length_c                   20.6184(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.954(3)
_cell_angle_gamma                90.00
_cell_volume                     3027.65(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4758
_cell_measurement_theta_min      0.79535
_cell_measurement_theta_max      1.00000

_exptl_crystal_description       Bulk
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.055
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             980
_exptl_absorpt_coefficient_mu    1.392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 

 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11413
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.29
_diffrn_reflns_theta_max         74.34
_reflns_number_total             5972
_reflns_number_gt                4601
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlisPro, Agilent Technologies,Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)'
_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)+(0.1000P)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_number_reflns         5972
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1593
_refine_ls_wR_factor_gt          0.1501
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.48395(2) 0.50961(3) 0.648467(15) 0.03928(14) Uani 1 1 d . . .
O1 O 0.52759(12) 0.68176(19) 0.39588(9) 0.0489(5) Uani 1 1 d . . .
O2 O 0.40429(12) 0.6562(2) 0.43997(9) 0.0498(5) Uani 1 1 d . . .
O3 O 0.47706(12) 0.64461(19) 0.57536(9) 0.0484(4) Uani 1 1 d . . .
O4 O 0.37055(14) 0.7749(2) 0.60925(11) 0.0671(6) Uani 1 1 d . . .
O5 O 0.46172(19) 0.2738(4) 1.28838(14) 0.0955(9) Uani 1 1 d . . .
O6 O 0.41977(17) 0.5023(3) 1.28844(13) 0.0808(8) Uani 1 1 d . . .
N1 N 0.39693(15) 0.4707(2) 0.71840(10) 0.0449(5) Uani 1 1 d . . .
N2 N 0.19791(14) 0.2746(3) 1.00533(10) 0.0473(5) Uani 1 1 d . . .
C1 C 0.46969(16) 0.7221(2) 0.43333(11) 0.0386(5) Uani 1 1 d . . .
C2 C 0.48698(14) 0.8631(2) 0.46972(11) 0.0341(5) Uani 1 1 d . . .
C3 C 0.46267(14) 0.8840(2) 0.53345(11) 0.0344(5) Uani 1 1 d . . .
C4 C 0.47511(15) 1.0207(2) 0.56303(12) 0.0350(5) Uani 1 1 d . . .
H1 H 0.4575 1.0353 0.6063 0.042 Uiso 1 1 calc R . .
C5 C 0.43195(17) 0.7587(3) 0.57576(11) 0.0396(5) Uani 1 1 d . . .
C6 C 0.3826(2) 0.3299(3) 0.73384(14) 0.0546(7) Uani 1 1 d . . .
H2 H 0.4014 0.2548 0.7054 0.066 Uiso 1 1 calc R . .
C7 C 0.3422(2) 0.2878(3) 0.78874(14) 0.0611(8) Uani 1 1 d . . .
H3 H 0.3333 0.1858 0.7975 0.073 Uiso 1 1 calc R . .
C8 C 0.31438(18) 0.3952(3) 0.83140(13) 0.0467(6) Uani 1 1 d . . .
C9 C 0.3283(2) 0.5404(3) 0.81450(15) 0.0579(8) Uani 1 1 d . . .
H4 H 0.3094 0.6179 0.8417 0.069 Uiso 1 1 calc R . .
C10 C 0.3691(2) 0.5740(3) 0.75862(14) 0.0573(7) Uani 1 1 d . . .
H5 H 0.3779 0.6752 0.7482 0.069 Uiso 1 1 calc R . .
C11 C 0.27228(17) 0.3527(3) 0.89168(12) 0.0481(6) Uani 1 1 d . . .
C12 C 0.2846(2) 0.2145(4) 0.91907(15) 0.0695(10) Uani 1 1 d . . .
H6 H 0.3194 0.1451 0.8984 0.083 Uiso 1 1 calc R . .
C13 C 0.2471(2) 0.1770(4) 0.97593(15) 0.0668(9) Uani 1 1 d . . .
H7 H 0.2560 0.0819 0.9945 0.080 Uiso 1 1 calc R . .
C14 C 0.18227(18) 0.4061(4) 0.97930(13) 0.0526(7) Uani 1 1 d . . .
H8 H 0.1452 0.4717 0.9999 0.063 Uiso 1 1 calc R . .
C15 C 0.21948(19) 0.4486(3) 0.92247(13) 0.0514(7) Uani 1 1 d . . .
H9 H 0.2088 0.5437 0.9046 0.062 Uiso 1 1 calc R . .
C16 C 0.16738(18) 0.2369(4) 1.07110(12) 0.0546(7) Uani 1 1 d . . .
H10 H 0.1542 0.1300 1.0732 0.066 Uiso 1 1 calc R . .
H11 H 0.1166 0.2934 1.0798 0.066 Uiso 1 1 calc R . .
C17 C 0.23238(18) 0.2742(4) 1.12104(12) 0.0515(7) Uani 1 1 d . . .
C18 C 0.2761(2) 0.1645(4) 1.15125(17) 0.0714(9) Uani 1 1 d . . .
H12 H 0.2651 0.0643 1.1403 0.086 Uiso 1 1 calc R . .
C19 C 0.3362(3) 0.1961(5) 1.19761(19) 0.0785(10) Uani 1 1 d . . .
H13 H 0.3659 0.1179 1.2180 0.094 Uiso 1 1 calc R . .
C20 C 0.3529(2) 0.3404(5) 1.21405(14) 0.0638(9) Uani 1 1 d . . .
C21 C 0.3089(2) 0.4543(4) 1.18352(17) 0.0718(10) Uani 1 1 d . . .
H14 H 0.3200 0.5544 1.1946 0.086 Uiso 1 1 calc R . .
C22 C 0.2486(2) 0.4213(4) 1.13671(15) 0.0650(8) Uani 1 1 d . . .
H15 H 0.2189 0.4987 1.1157 0.078 Uiso 1 1 calc R . .
C23 C 0.4157(2) 0.3717(5) 1.26723(17) 0.0735(10) 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 O3 1.9407(18) . ?
Zn1 O1 1.9633(17) 3_666 ?
Zn1 O6 2.021(3) 3_667 ?
Zn1 N1 2.067(2) . ?
Zn1 C23 2.595(4) 3_667 ?
O1 C1 1.280(3) . ?
O1 Zn1 1.9633(17) 3_666 ?
O2 C1 1.228(3) . ?
O3 C5 1.265(3) . ?
O4 C5 1.232(3) . ?
O5 C23 1.233(5) . ?
O6 C23 1.260(5) . ?
O6 Zn1 2.021(3) 3_667 ?
N1 C10 1.333(3) . ?
N1 C6 1.333(3) . ?
N2 C14 1.326(4) . ?
N2 C13 1.342(4) . ?
N2 C16 1.491(3) . ?
C1 C2 1.502(3) . ?
C2 C3 1.391(3) . ?
C2 C4 1.397(3) 3_676 ?
C3 C4 1.390(3) . ?
C3 C5 1.519(3) . ?
C4 C2 1.397(3) 3_676 ?
C6 C7 1.372(4) . ?
C7 C8 1.391(4) . ?
C8 C9 1.377(4) . ?
C8 C11 1.480(4) . ?
C9 C10 1.373(4) . ?
C11 C15 1.382(4) . ?
C11 C12 1.383(4) . ?
C12 C13 1.373(4) . ?
C14 C15 1.382(4) . ?
C16 C17 1.501(4) . ?
C17 C18 1.364(5) . ?
C17 C22 1.392(5) . ?
C18 C19 1.385(5) . ?
C19 C20 1.373(5) . ?
C20 C21 1.397(5) . ?
C20 C23 1.513(5) . ?
C21 C22 1.396(5) . ?
C23 Zn1 2.595(4) 3_667 ?

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
O3 Zn1 O1 100.83(8) . 3_666 ?
O3 Zn1 O6 124.57(11) . 3_667 ?
O1 Zn1 O6 108.65(10) 3_666 3_667 ?
O3 Zn1 N1 128.13(9) . . ?
O1 Zn1 N1 96.55(8) 3_666 . ?
O6 Zn1 N1 94.22(11) 3_667 . ?
O3 Zn1 C23 106.74(12) . 3_667 ?
O1 Zn1 C23 136.87(12) 3_666 3_667 ?
O6 Zn1 C23 28.34(12) 3_667 3_667 ?
N1 Zn1 C23 91.87(10) . 3_667 ?
C1 O1 Zn1 117.78(16) . 3_666 ?
C5 O3 Zn1 122.21(16) . . ?
C23 O6 Zn1 102.0(3) . 3_667 ?
C10 N1 C6 117.2(2) . . ?
C10 N1 Zn1 123.9(2) . . ?
C6 N1 Zn1 116.94(18) . . ?
C14 N2 C13 121.2(2) . . ?
C14 N2 C16 120.6(2) . . ?
C13 N2 C16 118.1(3) . . ?
O2 C1 O1 125.1(2) . . ?
O2 C1 C2 120.7(2) . . ?
O1 C1 C2 114.2(2) . . ?
C3 C2 C4 119.3(2) . 3_676 ?
C3 C2 C1 122.2(2) . . ?
C4 C2 C1 118.4(2) 3_676 . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 C5 117.2(2) . . ?
C2 C3 C5 122.8(2) . . ?
C3 C4 C2 121.2(2) . 3_676 ?
O4 C5 O3 125.1(2) . . ?
O4 C5 C3 120.7(2) . . ?
O3 C5 C3 114.1(2) . . ?
N1 C6 C7 123.3(3) . . ?
C6 C7 C8 119.6(3) . . ?
C9 C8 C7 116.6(3) . . ?
C9 C8 C11 122.7(2) . . ?
C7 C8 C11 120.7(3) . . ?
C10 C9 C8 120.4(3) . . ?
N1 C10 C9 122.8(3) . . ?
C15 C11 C12 117.7(3) . . ?
C15 C11 C8 121.5(3) . . ?
C12 C11 C8 120.7(2) . . ?
C13 C12 C11 120.5(3) . . ?
N2 C13 C12 120.0(3) . . ?
N2 C14 C15 120.5(3) . . ?
C11 C15 C14 120.0(3) . . ?
N2 C16 C17 109.3(2) . . ?
C18 C17 C22 119.5(3) . . ?
C18 C17 C16 120.4(3) . . ?
C22 C17 C16 120.1(3) . . ?
C17 C18 C19 121.4(4) . . ?
C20 C19 C18 120.0(4) . . ?
C19 C20 C21 119.4(3) . . ?
C19 C20 C23 119.0(4) . . ?
C21 C20 C23 121.6(4) . . ?
C22 C21 C20 120.2(3) . . ?
C17 C22 C21 119.5(3) . . ?
O5 C23 O6 121.4(4) . . ?
O5 C23 C20 121.4(4) . . ?
O6 C23 C20 117.2(4) . . ?
O5 C23 Zn1 71.9(2) . 3_667 ?
O6 C23 Zn1 49.62(19) . 3_667 ?
C20 C23 Zn1 166.4(3) . 3_667 ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        74.34
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.072
# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.022 -0.027 0.311 1309.1 189.6
_platon_squeeze_details          
; ?
;
_database_code_depnum_ccdc_archive 'CCDC 989780'
