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Presidents, 1910-93 | American Journal of Agricultural Economics | Oxford Academic
Presidents, 1910-93
American Journal of Agricultural Economics, Volume 74, Issue 5, 1 December 1992, Pages xi-xiii,
Presidents, 1910-93, American Journal of Agricultural Economics, Volume 74, Issue 5, 1 December 1992, Pages xi-xiii,
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and The title mononuclear complex, [Zn(C8H11N2O3S)2], is a zinc salt of 2-(2-pyridylmethylamino)ethanesulfonic acid (Hpmt). The ZnII ion is located on an inversion centre and is octahedrally surrounded by four N and two O atoms. The deprotonated pmt- anion coordinates in a facial arrangement through its two N atoms and one of the sulfonate O atoms. The crystal packing is determined by intermolecular N-HO and C-HO hydrogen bonds.Crystallographic Information File (CIF)
Contains datablocks global, IStructure factor file (CIF format)
Contains datablock I
Key indicators
Single-crystal X-ray study
Mean (C-C) = 0.003 &A
R factor = 0.023
wR factor = 0.062
Data-to-parameter ratio =
checkCIF/PLATON results
No syntax errors found
Alert level C
Large Non-Solvent
Ueq(max)/Ueq(min) ...
2.56 Ratio
Hirshfeld Test Diff (M-X)
Alert level G
Rescale T(min) & T(max) by .....................
The Model has Chirality at N2
(Verify) ....
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
2 ALERT level G = G check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
The complex (I) is isostructural with its analogues [Co(C8H11N2O3S)2]
(Li et al., 2006), [Ni(C8H11N2O3S)2] (Liao et
2007) and [Cu(C8H11N2O3S)2].2H2O (Li et al.,
2008), whose
structures have been described in detail. The six-coordinate ZnII ion
locates on a centre of symmetry with two deprotonated pmt- anions coordinate
in a tridentate facial arrangement with its three donor atoms (Fig.1). The
bond lengths and angles of (I) are in good agreement with its Co(II) and Ni(II)
analogues (Table 1).The N—H donor and SO acceptor groups of the pmt ions are involved in
hydrogen bonding interactions and forms a two-dimensional network in the
bc plane (Table 2 and Fig. 2).
For the structures of the Co(II) and Ni(II) analogues, see: Li et al.
(2008); Liao et al. (2007). For the preparation of the
Hpmt ligand,
see: Li et al. (2006).
The ligand Hpmt was prepared according to the method of Li et al.,
To the solution of Hpmt (2.0 mmol, 0.43 g) in water (25 ml), solid ZnCl2 (1 mmol, 0.14 g) was added. The resulting mixture was stirred at 333 K for 5 h,
then cooled to room temperature. After filtration, the filtrate was left to
stand at room temperature for slow evaporation. Colourless block-shaped
crystals suitable for X-ray diffraction were obtained in a yield of 42%.
Analysis, found: C 38.66, H 4.37, N 11.32, S 12.95%; C16H22N4O6S2Zn
requires: C 38.72, H 4.44, N 11.29, S 12.90%. IR (KBr, , cm-1): 771.3
[(C=C—H)], 746.5(CH2); 51.4, 1038.8( SO3-); 1607.2,
1572.3( C=C +
C=N); 3198.2( N—H).
H atoms bonded to C were positioned geometrically with C—H distance of
0.93&# Å, and treated as riding atoms, with Uiso(H)
=1.2Ueq(C). The N—H hydrogen atom was located in a difference
Fourier map and refined isotropically.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Molecular structure of (I), with displacement ellipsoids drawn at the 30%
probability level. Atoms with the suffix A are at the symmetry position
(-x, -y, -z).
The hydrogen bonding interactions in (I) (dashed lines) projected in bc
plane. H atoms on C atoms have been omitted.
[Zn(C8H11N2O3S)2]F(000) = 512Mr = 495.87Dx = 1.565 Mg m3Monoclinic, P21/cMo K radiation,
= 0.71073 ÅHall symbol:
-P 2ybcCell parameters from 4168 reflectionsa = 9.6288 (13) Å = 2.8&#°b = 10.0047 (13) ŵ = 1.41 mm1c = 11.3624 (15) ÅT = 291 K = 105.965 (1)°Block, colourlessV = )
Å30.50 × 0.39 × 0.29 mmZ = 2
Bruker APEXII CCD area-detector diffractometer2419 independent reflectionsRadiation source: fine-focus sealed tube2221 reflections with I > 2(I)Graphite monochromatorRint = 0.012 and
scansmax = 27.5°, min = 2.8°Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = 1112Tmin = 0.540, Tmax = 0.689k = 9126318 measured reflectionsl = 1414
Refinement on F2Primary atom site location: structure-invariant direct methodsLeast-squares matrix: fullSecondary atom site location: difference Fourier mapR[F2 > 2(F2)] = 0.023Hydrogen site location: inferred from neighbouring siteswR(F2) = 0.062H atoms treated by a mixture of independent and constrained refinementS = 1.07
w = 1/[2(Fo2) + (0.0322P)2 + 0.3355P]
where P = (Fo2 + 2Fc2)/32419 reflections(Δ/)max = 0.001137 parametersΔmax = 0.23 e Å30 restraintsΔmin = 0.38 e Å3
[Zn(C8H11N2O3S)2]V = )
Å3Mr = 495.87Z = 2Monoclinic, P21/cMo K radiationa = 9.6288 (13) ŵ = 1.41 mm1b = 10.0047 (13) ÅT = 291 Kc = 11.3624 (15) Å0.50 × 0.39 × 0.29 mm = 105.965 (1)°
Bruker APEXII CCD area-detector diffractometer2419 independent reflectionsAbsorption correction: multi-scan (SADABS; Sheldrick, 1996)2221 reflections with I > 2(I)Tmin = 0.540, Tmax = 0.689Rint = 0.0126318 measured reflections
R[F2 > 2(F2)] = 0.0230 restraintswR(F2) = 0.062H atoms treated by a mixture of independent and constrained refinementS = 1.07Δmax = 0.23 e Å32419 reflectionsΔmin = 0.38 e Å3137 parameters
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)are estimated using the full covariance matrix. The cell e.s.d.'s are takeninto account individually in the estimation of e.s.d.'s in distances, angles correlations between e.s.d.'s in cell parameters are onlyused when they are defined by crystal symmetry. An approximate (isotropic)treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
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 > (F2) is used only for calculating R-factors(gt)
etc. and is
not relevant to the choice of reflections for refinement. R-factors
on F2 are statistically about twice as large as those based on
factors based on ALL data will be even larger.
xyzUiso*/UeqZn10.50000.00000.50000.02437 (8)S10.63235 (4)0.29294 (4)0.45567 (3)0.02858 (10)O10.57188 (13)0.16226 (11)0.40792 (10)0.0375 (3)O20.55332 (14)0.40018 (12)0.37950 (10)0.0428 (3)O30.78676 (14)0.30037 (16)0.47547 (13)0.0573 (4)N10.27433 (14)0.03618 (13)0.39160 (12)0.0309 (3)N20.42452 (13)0.13247 (12)0.61609 (11)0.0274 (3)C10.2143 (2)0.02195 (18)0.27020 (16)0.0412 (4)H10.26770.01850.22320.049*C20.0760 (2)0.0655 (3)0.2137 (2)0.0633 (6)H20.03700.05490.12970.076*C30.0031 (2)0.1249 (3)0.2834 (2)0.0746 (7)H30.09610.15580.24680.090*C40.05670 (19)0.1385 (2)0.4085 (2)0.0584 (5)H40.00440.17750.45710.070*C50.19633 (16)0.09248 (16)0.45981 (15)0.0350 (3)C60.26892 (17)0.10136 (17)0.59524 (15)0.0360 (3)H6A0.22330.17070.63130.043*H6B0.25840.01710.63420.043*C70.44409 (17)0.27835 (15)0.59923 (13)0.0303 (3)H7A0.41840.32730.66390.036*H7B0.37960.30660.52170.036*C80.59850 (16)0.31189 (15)0.60131 (13)0.0292 (3)H8A0.66370.25420.65990.035*H8B0.61900.40340.62870.035*H1N0.4634 (18)0.1133 (17)0.6913 (16)0.032 (4)*
U11U22U33U12U13U23Zn10.02484 (13)0.02218 (13)0.02641 (12)0.00349 (8)0.00760 (9)0.00102 (8)S10.03239 (19)0.02599 (19)0.02848 (17)0.00050 (14)0.01027 (14)0.00143 (13)O10.0591 (7)0.0267 (6)0.0308 (5)0.0037 (5)0.0194 (5)0.0023 (4)O20.0672 (8)0.0301 (6)0.0319 (5)0.0094 (5)0.0148 (5)0.0068 (5)O30.0353 (7)0.0786 (11)0.0625 (8)0.0049 (6)0.0208 (6)0.0068 (7)N10.0272 (6)0.0305 (6)0.0330 (6)0.0024 (5)0.0051 (5)0.0010 (5)N20.0307 (6)0.0268 (6)0.0253 (6)0.0022 (5)0.0087 (5)0.0003 (5)C10.0404 (9)0.0424 (10)0.0366 (8)0.0027 (7)0.0035 (7)0.0020 (7)C20.0453 (11)0.0799 (16)0.0501 (11)0.0037 (11)0.0114 (9)0.0067 (11)C30.0310 (10)0.097 (2)0.0817 (16)0.0137 (11)0.0080 (10)0.0102 (15)C40.0270 (8)0.0691 (14)0.0786 (14)0.0112 (9)0.0137 (9)0.0001 (11)C50.0259 (7)0.0329 (8)0.0474 (9)0.0013 (6)0.0118 (6)0.0005 (7)C60.0327 (8)0.0387 (9)0.0430 (8)0.0013 (7)0.0210 (7)0.0030 (7)C70.0367 (8)0.0245 (7)0.0313 (7)0.0042 (6)0.0120 (6)0.0028 (6)C80.0348 (7)0.0268 (7)0.0241 (6)0.0009 (6)0.0048 (5)0.0029 (5)
Zn1—N22.1336 (12)C1—H10.9300Zn1—N2i2.1336 (12)C2—C31.376 (4)Zn1—O12.1465 (11)C2—H20.9300Zn1—O1i2.1465 (11)C3—C41.386 (3)Zn1—N1i2.2130 (13)C3—H30.9300Zn1—N12.2130 (13)C4—C51.388 (2)S1—O31.4431 (13)C4—H40.9300S1—O21.4549 (12)C5—C61.508 (2)S1—O11.4727 (11)C6—H6A0.9700S1—C81.7825 (15)C6—H6B0.9700N1—C51.342 (2)C7—C81.518 (2)N1—C11.349 (2)C7—H7A0.9700N2—C61.4841 (19)C7—H7B0.9700N2—C71.4908 (19)C8—H8A0.9700N2—H1N0.856 (17)C8—H8B0.9700C1—C21.380 (3)
N2—Zn1—N2i180.0N1H1119.0N2—Zn1—O192.40 (5)C2H1119.0N2i—Zn1—O187.60 (4)C3C1118.96 (19)N2—Zn1—O1i87.60 (5)C3H2120.5N2i—Zn1—O1i92.40 (5)C1H2120.5O1—Zn1—O1i180.0C2C4119.55 (18)N2—Zn1—N1i101.93 (5)C2H3120.2N2i—Zn1—N1i78.06 (5)C4H3120.2O1—Zn1—N1i89.78 (5)C3C5118.7 (2)O1i—Zn1—N1i90.22 (5)C3H4120.7N2—Zn1—N178.06 (5)C5H4120.7N2i—Zn1—N1101.94 (5)N1C4121.82 (16)O1—Zn1—N190.22 (5)N1C6115.98 (13)O1i—Zn1—N189.78 (5)C4C6122.19 (16)N1i—Zn1—N1180.0N2C5109.85 (12)O3O2113.74 (9)N2H6A109.7O3O1112.90 (8)C5H6A109.7O2O1110.27 (7)N2H6B109.7O3C8107.06 (8)C5H6B109.7O2C8105.93 (7)H6AH6B108.2O1C8106.36 (7)N2C8111.86 (12)S1Zn1129.76 (6)N2H7A109.2C5C1118.96 (14)C8H7A109.2C5Zn1111.53 (10)N2H7B109.2C1Zn1129.14 (12)C8H7B109.2C6C7110.03 (12)H7AH7B107.9C6Zn1105.77 (9)C7S1112.98 (10)C7Zn1116.88 (9)C7H8A109.0C6H1N104.9 (12)S1H8A109.0C7H1N108.2 (12)C7H8B109.0Zn1H1N110.4 (11)S1H8B109.0N1C2122.03 (19)H8AH8B107.8O3O1—Zn1103.94 (10)N1—Zn1C790.09 (10)O2O1—Zn1127.61 (9)C5C1—C21.1 (3)C8O1—Zn113.19 (11)Zn1C1—C2171.19 (16)N2—Zn1S133.74 (10)N1C2—C30.2 (3)N2i—Zn1S1146.26 (10)C1C3—C40.7 (4)N1i—Zn1S168.19 (10)C2C4—C50.7 (4)N1—Zn1S1111.81 (10)C1C5—C41.1 (3)N2—Zn1C514.41 (11)Zn1C5—C4172.45 (15)N2i—Zn1C5165.59 (11)C1C5—C6178.25 (15)O1—Zn1C5106.82 (11)Zn1C5—C68.16 (17)O1i—Zn1C573.18 (11)C3C5—N10.3 (3)N2—Zn1C1158.35 (15)C3C5—C6179.1 (2)N2i—Zn1C121.65 (15)C7C6—C580.21 (15)O1—Zn1C165.94 (14)Zn1C6—C546.87 (14)O1i—Zn1C1114.06 (14)N1C6—N237.7 (2)O1—Zn1C6122.46 (10)C4C6—N2142.93 (17)O1i—Zn1C657.54 (10)C6C7—C8171.67 (11)N1i—Zn1C6147.26 (9)Zn1C7—C851.08 (14)N1—Zn1C632.74 (9)N2C8—S185.42 (13)O1—Zn1C70.37 (10)O3C8—C7168.32 (11)O1i—Zn1C7179.63 (10)O2C8—C769.97 (12)N1i—Zn1C789.91 (10)O1C8—C747.37 (12)Symmetry code:
(i) x+1, y, z+1.
D—H···AD—HH···AD···AD—H···AN2—H1N···O2ii0.855 (18)2.079 (18)2.9259 (17)170.6 (16)C1··O2iii0.932.473.388 (2)169C4··O3iv0.932.493.324 (2)150C6—H6B···O1i0.972.563.056 (2)112C8—H8B···O2v0.972.563.265 (2)130Symmetry codes:
(i) x+1, y, z+1; (ii) x, y+1/2, z+1/2; (iii) x+1, y1/2, z+1/2; (iv) x1, y, z; (v) x+1, y+1, z+1.
Crystal dataChemical formula[Zn(C8H11N2O3S)2]Mr495.87Crystal system, space groupMonoclinic, P21/cTemperature (K)291a, b, c (Å)9.6288 (13), 10.0047 (13), 11.3624 (15) (°) 105.965 (1)V (Å3))Z2Radiation typeMo Kµ (mm1)1.41Crystal size (mm)0.50 × 0.39 × 0.29 Data collectionDiffractometerBruker APEXII CCD area-detector diffractometerAbsorption correctionMulti-scan (SADABS; Sheldrick, 1996)
Tmin, Tmax0.540, 0.689No. of measured, independent and observed [I > 2(I)] reflections, 2221
Rint0.012(sin /)max (Å1)0.650 RefinementR[F2 > 2(F2)], wR(F2), S 0.023,
1.07No. of reflections2419No. of parameters137H-atom treatmentH atoms treated by a mixture of independent and constrained refinementΔmax, Δmin (e Å3)0.23, 0.38
-->Selected geometric parameters (Å, º)
Zn1—N22.1336 (12)Zn1—N12.2130 (13)Zn1—O12.1465 (11)
N2—Zn1—O192.40 (5)O1—Zn1—N1i89.78 (5)N2i—Zn1—O187.60 (4)N2—Zn1—N178.06 (5)N2—Zn1—N1i101.93 (5)O1—Zn1—N190.22 (5)Symmetry code:
(i) x+1, y, z+1.
-->Hydrogen-bond geometry (Å, º)
D—H···AD—HH···AD···AD—H···AN2—H1N···O2ii0.855 (18)2.079 (18)2.;(17)170.6 (16)C1··O2iii0.93002.47003.388 (2)169.00C4··O3iv0.93002.49003.324 (2)150.00C6—H6B···O1i0.97002.56003.056 (2)112.00C8—H8B···O2v0.97002.56003.265 (2)130.00Symmetry codes:
(i) x+1, y, z+1; (ii) x, y+1/2, z+1/2; (iii) x+1, y1/2, z+1/2; (iv) x1, y, z; (v) x+1, y+1, z+1.
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