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

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#                 Cambridge Crystallographic Data Centre
#                                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_szg206

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N O8 P2 Zn'
_chemical_formula_weight         402.52

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'
P P 0.1023 0.0942 '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   'Pccn '

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

_cell_length_a                   18.5137(12)
_cell_length_b                   19.2404(12)
_cell_length_c                   8.0478(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2866.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1981
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      22.58

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    1.977
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5530
_exptl_absorpt_correction_T_max  0.9076
_exptl_absorpt_process_details   sadabs

_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  'Smart Apex II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13529
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2525
_reflns_number_gt                1910
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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^)+(0.0017P)^2^+8.1468P] 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_number_reflns         2525
_refine_ls_number_parameters     218
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0635
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.021
_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 1.16616(2) 0.17957(2) 0.20860(6) 0.02708(14) Uani 1 1 d . . .
P1 P 1.16941(6) 0.16203(6) 0.81517(12) 0.0270(3) Uani 1 1 d . . .
P2 P 1.01534(5) 0.12359(5) 0.37444(13) 0.0214(2) Uani 1 1 d . . .
O1 O 1.1684(3) 0.1305(3) 0.9941(6) 0.0310(18) Uani 0.497(7) 1 d PU . 1
O2 O 1.1359(3) 0.2245(3) 0.7922(10) 0.0304(17) Uani 0.497(7) 1 d PU . 1
O1' O 1.1331(3) 0.1849(3) 0.9804(6) 0.0300(18) Uani 0.503(7) 1 d PU . 2
O2' O 1.1552(3) 0.2279(3) 0.6925(9) 0.0310(16) Uani 0.503(7) 1 d PU . 2
O3 O 1.24493(16) 0.14564(16) 0.7863(6) 0.0746(12) Uani 1 1 d U . .
O4 O 1.09117(13) 0.12219(14) 0.3131(3) 0.0317(7) Uani 1 1 d U . .
O5 O 0.97317(14) 0.18476(14) 0.2885(3) 0.0318(7) Uani 1 1 d U . .
H5A H 0.9303 0.1825 0.3135 0.048 Uiso 1 1 calc R . .
O6 O 0.97513(13) 0.05631(13) 0.3592(3) 0.0271(6) Uani 1 1 d U . .
O7 O 0.66478(16) 0.16842(16) 0.8848(5) 0.0591(10) Uani 1 1 d U . .
O8 O 0.66310(17) 0.05485(16) 0.8635(6) 0.0923(17) Uani 1 1 d U . .
H8B H 0.6178 0.0621 0.8651 0.138 Uiso 1 1 d R . .
N1 N 1.03923(15) 0.09383(15) 0.7068(4) 0.0211(7) Uani 1 1 d . . .
H1C H 1.0246 0.0525 0.6634 0.025 Uiso 1 1 calc R . .
C1 C 1.0122(2) 0.1493(2) 0.5917(5) 0.0254(9) Uani 1 1 d . . .
H1A H 1.0412 0.1908 0.6066 0.031 Uiso 1 1 calc R . .
H1B H 0.9628 0.1606 0.6210 0.031 Uiso 1 1 calc R . .
C2 C 1.12102(18) 0.09145(19) 0.7144(5) 0.0241(9) Uani 1 1 d . . .
H2A H 1.1387 0.0882 0.6012 0.029 Uiso 1 1 calc R . .
H2B H 1.1345 0.0487 0.7702 0.029 Uiso 1 1 calc R . .
C3 C 1.0071(2) 0.0984(2) 0.8798(5) 0.0312(10) Uani 1 1 d . . .
H3A H 1.0233 0.0588 0.9443 0.037 Uiso 1 1 calc R . .
H3B H 1.0250 0.1401 0.9337 0.037 Uiso 1 1 calc R . .
C4 C 0.9257(2) 0.0999(2) 0.8798(5) 0.0273(10) Uani 1 1 d . . .
C5 C 0.8911(2) 0.1609(2) 0.9214(5) 0.0339(11) Uani 1 1 d . . .
H5 H 0.9182 0.1996 0.9508 0.041 Uiso 1 1 calc R . .
C6 C 0.8167(2) 0.1651(2) 0.9199(6) 0.0409(12) Uani 1 1 d . . .
H6 H 0.7939 0.2068 0.9461 0.049 Uiso 1 1 calc R . .
C7 C 0.7762(2) 0.1073(2) 0.8794(6) 0.0359(11) Uani 1 1 d . . .
C8 C 0.8104(2) 0.0452(2) 0.8417(6) 0.0453(14) Uani 1 1 d . . .
H8A H 0.7835 0.0060 0.8150 0.054 Uiso 1 1 d R . .
C9 C 0.8853(2) 0.0420(2) 0.8405(6) 0.0407(12) Uani 1 1 d . . .
H9 H 0.9083 0.0005 0.8130 0.049 Uiso 1 1 calc R . .
C10 C 0.6960(2) 0.1137(2) 0.8761(7) 0.0429(12) Uani 1 1 d . . .

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 0.0240(2) 0.0347(3) 0.0225(2) 0.0016(2) -0.0026(2) -0.0126(2)
P1 0.0175(5) 0.0446(7) 0.0190(5) -0.0003(5) 0.0004(4) -0.0107(5)
P2 0.0159(5) 0.0243(6) 0.0241(5) 0.0010(5) -0.0003(4) -0.0022(4)
O1 0.046(4) 0.028(4) 0.019(3) 0.003(2) -0.002(3) -0.001(3)
O2 0.029(3) 0.017(3) 0.046(4) 0.006(3) -0.007(3) 0.001(2)
O1' 0.017(3) 0.047(4) 0.025(3) -0.010(3) -0.003(2) 0.000(3)
O2' 0.032(4) 0.024(3) 0.036(4) 0.008(3) -0.005(3) -0.006(3)
O3 0.0163(15) 0.046(2) 0.161(4) -0.012(2) -0.002(2) -0.0038(15)
O4 0.0211(14) 0.0342(16) 0.0397(17) 0.0025(14) 0.0085(13) -0.0043(13)
O5 0.0270(15) 0.0321(16) 0.0363(16) 0.0106(14) -0.0030(14) -0.0020(13)
O6 0.0187(14) 0.0228(15) 0.0399(17) -0.0033(13) -0.0020(13) -0.0016(11)
O7 0.0216(17) 0.0286(19) 0.127(3) -0.0108(19) -0.003(2) 0.0024(15)
O8 0.0183(17) 0.030(2) 0.229(5) -0.035(3) 0.007(3) -0.0032(15)
N1 0.0170(16) 0.0187(17) 0.0275(17) -0.0015(15) -0.0014(15) -0.0020(13)
C1 0.022(2) 0.026(2) 0.028(2) -0.0025(18) -0.0021(18) 0.0035(18)
C2 0.0129(19) 0.023(2) 0.037(2) 0.004(2) -0.0008(19) 0.0021(16)
C3 0.019(2) 0.049(3) 0.025(2) 0.004(2) 0.0029(19) 0.001(2)
C4 0.018(2) 0.037(3) 0.027(2) 0.004(2) 0.0020(18) 0.0007(18)
C5 0.027(2) 0.026(3) 0.049(3) -0.002(2) 0.001(2) -0.0100(19)
C6 0.024(3) 0.026(3) 0.073(3) -0.010(2) 0.003(2) -0.0024(19)
C7 0.019(2) 0.028(2) 0.061(3) -0.004(2) 0.006(2) 0.0001(18)
C8 0.021(2) 0.032(3) 0.083(4) -0.014(3) 0.003(2) -0.0034(19)
C9 0.027(2) 0.031(3) 0.064(3) -0.008(2) 0.005(2) 0.003(2)
C10 0.024(2) 0.029(3) 0.075(4) -0.009(3) 0.005(2) -0.005(2)

_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' 1.796(6) 7_565 ?
Zn1 O3 1.878(3) 8_855 ?
Zn1 O1' 1.939(5) 1_554 ?
Zn1 O4 1.963(3) . ?
Zn1 O1 1.968(5) 1_554 ?
Zn1 O2 2.043(6) 7_565 ?
P1 O2 1.365(6) . ?
P1 O3 1.452(3) . ?
P1 O1' 1.553(5) . ?
P1 O1 1.562(5) . ?
P1 O2' 1.628(6) . ?
P1 C2 1.818(4) . ?
P2 O4 1.488(3) . ?
P2 O6 1.498(3) . ?
P2 O5 1.572(3) . ?
P2 C1 1.818(4) . ?
O1 Zn1 1.968(5) 1_556 ?
O2 Zn1 2.043(6) 7_566 ?
O1' Zn1 1.939(5) 1_556 ?
O2' Zn1 1.796(6) 7_566 ?
O3 Zn1 1.878(3) 8_856 ?
O5 H5A 0.8200 . ?
O7 C10 1.203(5) . ?
O8 C10 1.290(5) . ?
O8 H8B 0.8501 . ?
N1 C1 1.499(5) . ?
N1 C3 1.517(5) . ?
N1 C2 1.516(4) . ?
N1 H1C 0.9100 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.508(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.377(5) . ?
C4 C9 1.380(6) . ?
C5 C6 1.380(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(6) . ?
C7 C10 1.491(6) . ?
C8 C9 1.387(6) . ?
C8 H8A 0.9299 . ?
C9 H9 0.9300 . ?

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 O3 117.9(2) 7_565 8_855 ?
O2' Zn1 O1' 81.0(3) 7_565 1_554 ?
O3 Zn1 O1' 127.6(2) 8_855 1_554 ?
O2' Zn1 O4 120.5(2) 7_565 . ?
O3 Zn1 O4 106.35(14) 8_855 . ?
O1' Zn1 O4 102.29(18) 1_554 . ?
O2' Zn1 O1 114.5(3) 7_565 1_554 ?
O3 Zn1 O1 96.2(2) 8_855 1_554 ?
O1' Zn1 O1 37.0(2) 1_554 1_554 ?
O4 Zn1 O1 96.96(18) . 1_554 ?
O2' Zn1 O2 25.5(2) 7_565 7_565 ?
O3 Zn1 O2 116.4(2) 8_855 7_565 ?
O1' Zn1 O2 100.2(3) 1_554 7_565 ?
O4 Zn1 O2 100.0(2) . 7_565 ?
O1 Zn1 O2 136.7(3) 1_554 7_565 ?
O2 P1 O3 127.4(3) . . ?
O2 P1 O1' 70.7(4) . . ?
O3 P1 O1' 127.9(3) . . ?
O2 P1 O1 117.4(4) . . ?
O3 P1 O1 94.3(3) . . ?
O1' P1 O1 46.8(3) . . ?
O2 P1 O2' 32.8(3) . . ?
O3 P1 O2' 103.2(3) . . ?
O1' P1 O2' 103.2(3) . . ?
O1 P1 O2' 149.2(3) . . ?
O2 P1 C2 111.9(3) . . ?
O3 P1 C2 103.94(18) . . ?
O1' P1 C2 112.4(2) . . ?
O1 P1 C2 96.6(2) . . ?
O2' P1 C2 103.4(3) . . ?
O4 P2 O6 115.21(16) . . ?
O4 P2 O5 109.65(16) . . ?
O6 P2 O5 111.35(15) . . ?
O4 P2 C1 110.73(18) . . ?
O6 P2 C1 107.31(17) . . ?
O5 P2 C1 101.74(17) . . ?
P1 O1 Zn1 128.5(3) . 1_556 ?
P1 O2 Zn1 135.6(4) . 7_566 ?
P1 O1' Zn1 131.2(3) . 1_556 ?
P1 O2' Zn1 135.2(4) . 7_566 ?
P1 O3 Zn1 145.3(2) . 8_856 ?
P2 O4 Zn1 143.03(18) . . ?
P2 O5 H5A 109.5 . . ?
C10 O8 H8B 108.7 . . ?
C1 N1 C3 113.3(3) . . ?
C1 N1 C2 112.3(3) . . ?
C3 N1 C2 110.9(3) . . ?
C1 N1 H1C 106.6 . . ?
C3 N1 H1C 106.6 . . ?
C2 N1 H1C 106.6 . . ?
N1 C1 P2 113.0(3) . . ?
N1 C1 H1A 109.0 . . ?
P2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
P2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N1 C2 P1 119.2(3) . . ?
N1 C2 H2A 107.5 . . ?
P1 C2 H2A 107.5 . . ?
N1 C2 H2B 107.5 . . ?
P1 C2 H2B 107.5 . . ?
H2A C2 H2B 107.0 . . ?
C4 C3 N1 113.1(3) . . ?
C4 C3 H3A 109.0 . . ?
N1 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
N1 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C9 119.4(4) . . ?
C5 C4 C3 118.8(4) . . ?
C9 C4 C3 121.8(4) . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.8(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 119.9(4) . . ?
C6 C7 C10 118.6(4) . . ?
C8 C7 C10 121.5(4) . . ?
C7 C8 C9 119.8(4) . . ?
C7 C8 H8A 120.3 . . ?
C9 C8 H8A 119.8 . . ?
C4 C9 C8 120.2(4) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
O7 C10 O8 123.1(4) . . ?
O7 C10 C7 123.3(4) . . ?
O8 C10 C7 113.5(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5A O7 0.82 1.87 2.687(4) 173.5 8_755
O8 H8B O6 0.85 1.72 2.560(4) 166.6 8_756
N1 H1C O6 0.91 2.10 2.949(4) 154.6 5_756

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.079
_database_code_depnum_ccdc_archive 'CCDC 890806'