# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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#  data retrieval see:
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data_ThrZnOAc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ThrZnOAc
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N2 O5 Zn, 5H2(O)'
_chemical_formula_sum            'C12 H26 N2 O10 Zn'
_chemical_formula_weight         423.66
_chemical_absolute_configuration syn
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           Hexagonal
_symmetry_space_group_name_H-M   P61

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x-y, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'

_cell_length_a                   17.4807(3)
_cell_length_b                   17.4807(3)
_cell_length_c                   10.4350(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2761.47(9)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      28.06

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_exptl_absorpt_coefficient_mu    1.385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_T_max  0.758
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            7339
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         28.06
_reflns_number_total             3155
_reflns_number_gt                3035
_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 F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w=1/[\s^2^(Fo^2^)+(0.0795P)^2^+9.1266P] where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    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(10)
_refine_ls_number_reflns         3155
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1378
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.050
_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 0.46481(4) 0.53607(4) 0.08799(8) 0.01521(17) Uani 1 1 d . . .
O1 O 0.4905(2) 0.5164(2) 0.2809(4) 0.0182(8) Uani 1 1 d . . .
O2 O 0.5605(3) 0.4615(3) 0.3931(4) 0.0273(10) Uani 1 1 d . . .
O3 O 0.6707(4) 0.5461(5) 0.0502(7) 0.078(2) Uani 1 1 d . . .
H3 H 0.6525 0.5789 0.0742 0.117 Uiso 1 1 d R . .
O4 O 0.5360(3) 0.6651(3) 0.0943(5) 0.0317(10) Uani 1 1 d . . .
O5 O 0.6627(8) 0.6851(8) 0.1796(12) 0.121(4) Uiso 1 1 d . . .
O6 O 0.1735(17) 0.2248(16) 0.065(3) 0.279(12) Uani 1 1 d . . .
O7 O 0.2441(11) 0.2122(11) 0.273(3) 0.210(9) Uani 1 1 d . . .
O8 O 0.070(3) 0.077(3) 0.638(7) 0.47(3) Uiso 1 1 d . . .
O9 O 0.0278(13) 0.2108(10) 0.021(2) 0.222(10) Uani 1 1 d . . .
O10 O 0.2314(15) 0.0471(13) 0.285(4) 0.326(16) Uani 1 1 d . . .
N1 N 0.4912(3) 0.1577(3) -0.0410(4) 0.0174(9) Uani 1 1 d . . .
N2 N 0.4960(3) 0.4366(3) 0.0625(4) 0.0150(9) Uani 1 1 d . . .
H2 H 0.5300 0.4493 -0.0090 0.018 Uiso 1 1 d R . .
C1 C 0.5026(4) 0.2201(4) -0.1264(6) 0.0263(13) Uani 1 1 d . . .
H1 H 0.5305 0.2229 -0.2037 0.032 Uiso 1 1 calc R . .
C2 C 0.4748(5) 0.2801(4) -0.1043(6) 0.0289(13) Uani 1 1 d . . .
H2A H 0.4832 0.3218 -0.1664 0.035 Uiso 1 1 calc R . .
C3 C 0.4343(4) 0.2783(4) 0.0108(6) 0.0220(12) Uani 1 1 d . . .
C4 C 0.4206(4) 0.2132(4) 0.0978(7) 0.0284(13) Uani 1 1 d . . .
H4 H 0.3925 0.2088 0.1754 0.034 Uiso 1 1 calc R . .
C5 C 0.4493(4) 0.1541(4) 0.0682(6) 0.0252(12) Uani 1 1 d . . .
H5 H 0.4390 0.1100 0.1270 0.030 Uiso 1 1 calc R . .
C6 C 0.4126(3) 0.3496(4) 0.0414(6) 0.0206(11) Uani 1 1 d . . .
H6A H 0.3793 0.3551 -0.0287 0.025 Uiso 1 1 calc R . .
H6B H 0.3763 0.3335 0.1179 0.025 Uiso 1 1 calc R . .
C7 C 0.5471(3) 0.4340(4) 0.1719(5) 0.0157(10) Uani 1 1 d . . .
H7 H 0.5264 0.3717 0.1911 0.019 Uiso 1 1 calc R . .
C8 C 0.5311(3) 0.4750(4) 0.2911(5) 0.0160(11) Uani 1 1 d . . .
C9 C 0.6478(4) 0.4790(4) 0.1397(6) 0.0241(12) Uani 1 1 d . . .
H9 H 0.6825 0.5035 0.2181 0.029 Uiso 1 1 calc R . .
C10 C 0.6732(7) 0.4173(7) 0.0769(13) 0.072(3) Uiso 1 1 d . . .
H10A H 0.6308 0.3574 0.0990 0.108 Uiso 1 1 calc R . .
H10B H 0.7307 0.4307 0.1062 0.108 Uiso 1 1 calc R . .
H10C H 0.6743 0.4243 -0.0144 0.108 Uiso 1 1 calc R . .
C11 C 0.6139(7) 0.7097(7) 0.1010(12) 0.067(2) Uiso 1 1 d . . .
C12 C 0.6595(5) 0.8065(5) 0.0946(15) 0.070(3) Uani 1 1 d . . .
H12A H 0.6474 0.8243 0.0136 0.106 Uiso 1 1 calc R . .
H12B H 0.7220 0.8300 0.1033 0.106 Uiso 1 1 calc R . .
H12C H 0.6389 0.8286 0.1626 0.106 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0228(3) 0.0232(3) 0.0081(3) 0.0001(2) 0.0005(2) 0.0178(3)
O1 0.0252(18) 0.0303(19) 0.0068(19) -0.0028(15) -0.0003(14) 0.0197(16)
O2 0.040(2) 0.056(3) 0.006(2) -0.0043(17) -0.0044(17) 0.039(2)
O3 0.030(3) 0.118(6) 0.072(5) 0.067(4) 0.016(3) 0.026(3)
O4 0.036(2) 0.026(2) 0.031(3) -0.002(2) -0.012(2) 0.0142(18)
O6 0.26(2) 0.24(2) 0.30(3) 0.02(2) -0.03(3) 0.09(2)
O7 0.159(12) 0.194(16) 0.31(3) 0.090(18) 0.026(16) 0.114(12)
O9 0.222(18) 0.114(11) 0.32(3) -0.036(13) -0.040(18) 0.075(12)
O10 0.25(2) 0.184(17) 0.58(5) 0.12(3) -0.05(3) 0.137(17)
N1 0.029(2) 0.014(2) 0.010(2) -0.0002(16) -0.0012(17) 0.0108(18)
N2 0.021(2) 0.020(2) 0.006(2) -0.0011(16) -0.0010(16) 0.0119(17)
C1 0.050(4) 0.022(3) 0.010(3) 0.003(2) 0.008(2) 0.020(3)
C2 0.054(4) 0.022(3) 0.017(3) 0.005(2) 0.003(3) 0.023(3)
C3 0.026(3) 0.018(3) 0.018(3) 0.000(2) -0.003(2) 0.008(2)
C4 0.038(3) 0.032(3) 0.023(3) 0.009(3) 0.011(3) 0.023(3)
C5 0.040(3) 0.021(3) 0.017(3) 0.007(2) 0.008(2) 0.017(2)
C6 0.018(3) 0.023(3) 0.022(3) 0.000(2) -0.003(2) 0.012(2)
C7 0.023(3) 0.029(3) 0.005(2) 0.0004(19) -0.0016(19) 0.020(2)
C8 0.017(2) 0.027(3) 0.010(3) 0.0002(19) -0.0002(18) 0.015(2)
C9 0.017(3) 0.042(3) 0.017(3) 0.003(2) -0.001(2) 0.017(2)
C12 0.035(4) 0.040(4) 0.131(10) 0.020(6) 0.009(6) 0.015(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O4 1.958(4) . ?
Zn1 N1 2.059(4) 2 ?
Zn1 N2 2.083(4) . ?
Zn1 O2 2.087(4) 4_664 ?
Zn1 O1 2.127(4) . ?
O1 C8 1.247(6) . ?
O2 C8 1.255(7) . ?
O2 Zn1 2.087(4) 4_665 ?
O3 C9 1.393(8) . ?
O3 H3 0.8201 . ?
O4 C11 1.185(11) . ?
O5 C11 1.397(14) . ?
N1 C5 1.339(7) . ?
N1 C1 1.344(7) . ?
N1 Zn1 2.059(4) 6_554 ?
N2 C7 1.465(6) . ?
N2 C6 1.506(7) . ?
N2 H2 0.9101 . ?
C1 C2 1.379(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.380(8) . ?
C3 C6 1.507(8) . ?
C4 C5 1.390(8) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.529(7) . ?
C7 C9 1.564(7) . ?
C7 H7 0.9800 . ?
C9 C10 1.506(12) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.468(13) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
O4 Zn1 N1 112.21(18) . 2 ?
O4 Zn1 N2 133.24(18) . . ?
N1 Zn1 N2 114.42(18) 2 . ?
O4 Zn1 O2 91.62(19) . 4_664 ?
N1 Zn1 O2 89.21(17) 2 4_664 ?
N2 Zn1 O2 92.27(17) . 4_664 ?
O4 Zn1 O1 95.17(18) . . ?
N1 Zn1 O1 92.46(16) 2 . ?
N2 Zn1 O1 79.73(15) . . ?
O2 Zn1 O1 171.80(16) 4_664 . ?
C8 O1 Zn1 113.7(3) . . ?
C8 O2 Zn1 135.4(4) . 4_665 ?
C9 O3 H3 109.6 . . ?
C11 O4 Zn1 128.3(6) . . ?
C5 N1 C1 117.3(5) . . ?
C5 N1 Zn1 121.9(4) . 6_554 ?
C1 N1 Zn1 120.8(4) . 6_554 ?
C7 N2 C6 112.3(4) . . ?
C7 N2 Zn1 110.2(3) . . ?
C6 N2 Zn1 109.7(3) . . ?
C7 N2 H2 108.1 . . ?
C6 N2 H2 108.1 . . ?
Zn1 N2 H2 108.3 . . ?
N1 C1 C2 122.7(5) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 119.8(5) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 117.7(5) . . ?
C4 C3 C6 122.1(5) . . ?
C2 C3 C6 120.0(5) . . ?
C3 C4 C5 119.2(6) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 123.1(5) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
N2 C6 C3 110.5(4) . . ?
N2 C6 H6A 109.5 . . ?
C3 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N2 C7 C8 111.2(4) . . ?
N2 C7 C9 111.6(4) . . ?
C8 C7 C9 111.2(4) . . ?
N2 C7 H7 107.5 . . ?
C8 C7 H7 107.5 . . ?
C9 C7 H7 107.5 . . ?
O1 C8 O2 126.0(5) . . ?
O1 C8 C7 119.6(5) . . ?
O2 C8 C7 114.4(4) . . ?
O3 C9 C10 104.4(7) . . ?
O3 C9 C7 110.2(5) . . ?
C10 C9 C7 113.2(6) . . ?
O3 C9 H9 109.7 . . ?
C10 C9 H9 109.7 . . ?
C7 C9 H9 109.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 O5 120.6(10) . . ?
O4 C11 C12 122.6(9) . . ?
O5 C11 C12 108.6(10) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Zn1 O1 C8 -116.8(4) . . . . ?
N1 Zn1 O1 C8 130.6(4) 2 . . . ?
N2 Zn1 O1 C8 16.2(4) . . . . ?
O2 Zn1 O1 C8 29.0(13) 4_664 . . . ?
N1 Zn1 O4 C11 164.5(9) 2 . . . ?
N2 Zn1 O4 C11 -11.1(9) . . . . ?
O2 Zn1 O4 C11 -105.7(9) 4_664 . . . ?
O1 Zn1 O4 C11 69.7(9) . . . . ?
O4 Zn1 N2 C7 66.5(4) . . . . ?
N1 Zn1 N2 C7 -109.0(3) 2 . . . ?
O2 Zn1 N2 C7 160.8(3) 4_664 . . . ?
O1 Zn1 N2 C7 -21.0(3) . . . . ?
O4 Zn1 N2 C6 -169.4(3) . . . . ?
N1 Zn1 N2 C6 15.1(4) 2 . . . ?
O2 Zn1 N2 C6 -75.0(4) 4_664 . . . ?
O1 Zn1 N2 C6 103.2(4) . . . . ?
C5 N1 C1 C2 1.3(9) . . . . ?
Zn1 N1 C1 C2 -179.0(5) 6_554 . . . ?
N1 C1 C2 C3 0.9(10) . . . . ?
C1 C2 C3 C4 -2.3(9) . . . . ?
C1 C2 C3 C6 173.4(6) . . . . ?
C2 C3 C4 C5 1.4(9) . . . . ?
C6 C3 C4 C5 -174.2(6) . . . . ?
C1 N1 C5 C4 -2.3(9) . . . . ?
Zn1 N1 C5 C4 178.1(5) 6_554 . . . ?
C3 C4 C5 N1 0.9(10) . . . . ?
C7 N2 C6 C3 -62.3(6) . . . . ?
Zn1 N2 C6 C3 174.8(4) . . . . ?
C4 C3 C6 N2 107.0(6) . . . . ?
C2 C3 C6 N2 -68.5(7) . . . . ?
C6 N2 C7 C8 -99.6(5) . . . . ?
Zn1 N2 C7 C8 23.0(5) . . . . ?
C6 N2 C7 C9 135.5(5) . . . . ?
Zn1 N2 C7 C9 -101.8(4) . . . . ?
Zn1 O1 C8 O2 173.6(5) . . . . ?
Zn1 O1 C8 C7 -7.6(6) . . . . ?
Zn1 O2 C8 O1 19.6(9) 4_665 . . . ?
Zn1 O2 C8 C7 -159.3(4) 4_665 . . . ?
N2 C7 C8 O1 -10.6(7) . . . . ?
C9 C7 C8 O1 114.4(5) . . . . ?
N2 C7 C8 O2 168.4(5) . . . . ?
C9 C7 C8 O2 -66.6(6) . . . . ?
N2 C7 C9 O3 30.3(7) . . . . ?
C8 C7 C9 O3 -94.5(6) . . . . ?
N2 C7 C9 C10 -86.1(7) . . . . ?
C8 C7 C9 C10 149.1(7) . . . . ?
Zn1 O4 C11 O5 -40.2(15) . . . . ?
Zn1 O4 C11 C12 174.9(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.881
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.305
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.107
_database_code_depnum_ccdc_archive 'CCDC 943050'