# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2015

 
data_11cfm 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C5 H11 N O6 Zn' 
_chemical_formula_weight          246.52 
 
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    'P212121' 
 
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                    7.1859(8) 
_cell_length_b                    10.3982(12) 
_cell_length_c                    11.1230(13) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      831.12(16) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        'BLOCKS'
_exptl_crystal_colour             'COLOURLESS' 
_exptl_crystal_size_max           0.46 
_exptl_crystal_size_mid           0.28 
_exptl_crystal_size_min           0.22 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.970 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              504 
_exptl_absorpt_coefficient_mu     2.955 
_exptl_absorpt_correction_type    'MULTI-SCAN'
_exptl_absorpt_correction_T_min   0.3435 
_exptl_absorpt_correction_T_max   0.5626 
_exptl_absorpt_process_details    'BRUKER SADABS' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(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   'BRUKER SMART APEX  CCD DIFFRACTOMETER' 
_diffrn_measurement_method        'OMEGA-PHI SCAN' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             4913 
_diffrn_reflns_av_R_equivalents   0.0251 
_diffrn_reflns_av_sigmaI/netI     0.0403 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          2.68 
_diffrn_reflns_theta_max          27.50 
_reflns_number_total              1892 
_reflns_number_gt                 1829 
_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     'ORTEP' 
_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)+(0.0141P)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    0.048(12) 
_refine_ls_number_reflns          1892 
_refine_ls_number_parameters      134 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0239 
_refine_ls_R_factor_gt            0.0225 
_refine_ls_wR_factor_ref          0.0483 
_refine_ls_wR_factor_gt           0.0478 
_refine_ls_goodness_of_fit_ref    1.045 
_refine_ls_restrained_S_all       1.045 
_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 0.62279(4) 0.07076(2) 0.54087(2) 0.00910(8) Uani 1 1 d . . . 
O1 O 0.4802(2) 0.24550(15) 0.51587(15) 0.0120(4) Uani 1 1 d . . . 
O2 O 0.3604(2) 0.37355(14) 0.37447(14) 0.0115(3) Uani 1 1 d . . . 
O3 O 0.1980(2) 0.03827(15) 0.05332(15) 0.0146(4) Uani 1 1 d . . . 
O4 O 0.0162(2) -0.03569(14) 0.19717(15) 0.0123(4) Uani 1 1 d . . . 
O5 O 0.6949(3) -0.11927(17) 0.51979(18) 0.0167(4) Uani 1 1 d . . . 
H5C H 0.650(4) -0.178(3) 0.542(3) 0.017(8) Uiso 1 1 d . . . 
H5D H 0.788(5) -0.146(3) 0.489(3) 0.042(11) Uiso 1 1 d . . . 
O6 O 0.9676(3) 0.34793(17) 0.08452(18) 0.0135(4) Uani 1 1 d . . . 
H6C H 0.977(5) 0.381(3) 0.155(3) 0.048(11) Uiso 1 1 d . . . 
H6D H 0.898(4) 0.387(3) 0.047(3) 0.023(8) Uiso 1 1 d . . . 
C1 C 0.4640(3) 0.2828(2) 0.4093(2) 0.0100(5) Uani 1 1 d . . . 
C2 C 0.5733(3) 0.2136(2) 0.3097(2) 0.0103(5) Uani 1 1 d . . . 
H2 H 0.6577 0.2759 0.2725 0.012 Uiso 1 1 calc R . . 
C3 C 0.4399(3) 0.1648(2) 0.2128(2) 0.0109(5) Uani 1 1 d . . . 
H3A H 0.3813 0.2381 0.1745 0.013 Uiso 1 1 calc R . . 
H3B H 0.5110 0.1195 0.1520 0.013 Uiso 1 1 calc R . . 
C4 C 0.2893(3) 0.0759(2) 0.2601(2) 0.0124(4) Uani 1 1 d . . . 
H4A H 0.2144 0.1222 0.3183 0.015 Uiso 1 1 calc R . . 
H4B H 0.3475 0.0042 0.3013 0.015 Uiso 1 1 calc R . . 
C5 C 0.1632(3) 0.0242(2) 0.1620(2) 0.0104(5) Uani 1 1 d . . . 
N1 N 0.6867(3) 0.10876(18) 0.36131(18) 0.0108(4) Uani 1 1 d . . . 
H1A H 0.8078 0.1300 0.3557 0.013 Uiso 1 1 calc R . . 
H1B H 0.6688 0.0368 0.3178 0.013 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 0.00872(12) 0.00960(11) 0.00898(12) 0.00020(11) 0.00070(11) 0.00034(11) 
O1 0.0133(9) 0.0110(7) 0.0116(10) -0.0002(7) 0.0015(6) 0.0023(6) 
O2 0.0093(8) 0.0115(7) 0.0137(8) 0.0009(7) 0.0016(7) 0.0010(7) 
O3 0.0139(8) 0.0195(9) 0.0105(9) -0.0006(7) -0.0005(7) -0.0023(7) 
O4 0.0093(9) 0.0140(8) 0.0135(9) -0.0002(7) -0.0013(6) -0.0014(6) 
O5 0.0141(9) 0.0085(8) 0.0275(12) -0.0009(8) 0.0069(8) -0.0016(7) 
O6 0.0138(9) 0.0150(8) 0.0117(9) -0.0022(8) -0.0016(7) 0.0024(8) 
C1 0.0056(11) 0.0101(10) 0.0144(12) -0.0016(10) -0.0003(9) -0.0033(9) 
C2 0.0079(12) 0.0101(10) 0.0128(12) 0.0017(9) -0.0011(8) -0.0011(9) 
C3 0.0107(12) 0.0139(11) 0.0082(12) 0.0008(9) -0.0008(8) 0.0013(10) 
C4 0.0134(11) 0.0158(11) 0.0080(11) -0.0006(11) -0.0026(9) -0.0006(12) 
C5 0.0097(13) 0.0100(10) 0.0115(12) -0.0024(9) -0.0029(9) 0.0024(9) 
N1 0.0087(9) 0.0122(9) 0.0114(10) -0.0014(8) -0.0013(7) 0.0014(7) 
 
_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 2.0338(17) 4_556 ? 
Zn1 O4 2.0377(17) 2 ? 
Zn1 O5 2.0562(18) . ? 
Zn1 N1 2.087(2) . ? 
Zn1 O1 2.1046(15) . ? 
O1 C1 1.252(3) . ? 
O2 C1 1.263(3) . ? 
O2 Zn1 2.0339(17) 4_456 ? 
O3 C5 1.243(3) . ? 
O4 C5 1.287(3) . ? 
O4 Zn1 2.0376(17) 2_554 ? 
O5 H5C 0.73(3) . ? 
O5 H5D 0.80(3) . ? 
O6 H6C 0.86(4) . ? 
O6 H6D 0.76(3) . ? 
C1 C2 1.537(3) . ? 
C2 N1 1.477(3) . ? 
C2 C3 1.528(3) . ? 
C2 H2 0.9800 . ? 
C3 C4 1.517(3) . ? 
C3 H3A 0.9700 . ? 
C3 H3B 0.9700 . ? 
C4 C5 1.517(3) . ? 
C4 H4A 0.9700 . ? 
C4 H4B 0.9700 . ? 
N1 H1A 0.9000 . ? 
N1 H1B 0.9000 . ? 
 
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 O4 93.85(7) 4_556 2 ? 
O2 Zn1 O5 96.60(7) 4_556 . ? 
O4 Zn1 O5 92.80(7) 2 . ? 
O2 Zn1 N1 101.79(7) 4_556 . ? 
O4 Zn1 N1 163.37(7) 2 . ? 
O5 Zn1 N1 90.99(8) . . ? 
O2 Zn1 O1 102.95(6) 4_556 . ? 
O4 Zn1 O1 91.64(6) 2 . ? 
O5 Zn1 O1 159.61(7) . . ? 
N1 Zn1 O1 79.47(7) . . ? 
C1 O1 Zn1 115.95(14) . . ? 
C1 O2 Zn1 124.45(15) . 4_456 ? 
C5 O4 Zn1 103.25(14) . 2_554 ? 
Zn1 O5 H5C 131(2) . . ? 
Zn1 O5 H5D 126(2) . . ? 
H5C O5 H5D 103(3) . . ? 
H6C O6 H6D 109(3) . . ? 
O1 C1 O2 125.2(2) . . ? 
O1 C1 C2 119.3(2) . . ? 
O2 C1 C2 115.5(2) . . ? 
N1 C2 C3 112.06(17) . . ? 
N1 C2 C1 110.32(19) . . ? 
C3 C2 C1 110.08(18) . . ? 
N1 C2 H2 108.1 . . ? 
C3 C2 H2 108.1 . . ? 
C1 C2 H2 108.1 . . ? 
C4 C3 C2 113.89(19) . . ? 
C4 C3 H3A 108.8 . . ? 
C2 C3 H3A 108.8 . . ? 
C4 C3 H3B 108.8 . . ? 
C2 C3 H3B 108.8 . . ? 
H3A C3 H3B 107.7 . . ? 
C3 C4 C5 113.1(2) . . ? 
C3 C4 H4A 109.0 . . ? 
C5 C4 H4A 109.0 . . ? 
C3 C4 H4B 109.0 . . ? 
C5 C4 H4B 109.0 . . ? 
H4A C4 H4B 107.8 . . ? 
O3 C5 O4 121.2(2) . . ? 
O3 C5 C4 122.5(2) . . ? 
O4 C5 C4 116.3(2) . . ? 
C2 N1 Zn1 112.96(14) . . ? 
C2 N1 H1A 109.0 . . ? 
Zn1 N1 H1A 109.0 . . ? 
C2 N1 H1B 109.0 . . ? 
Zn1 N1 H1B 109.0 . . ? 
H1A N1 H1B 107.8 . . ? 
 
_diffrn_measured_fraction_theta_max    0.997 
_diffrn_reflns_theta_full              27.50 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.357 
_refine_diff_density_min   -0.299 
_refine_diff_density_rms    0.067 
