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Acta Cryst. (2008). E64, o750    [ doi:10.1107/S1600536808007988 ]

N'-(3-Ethoxy-2-hydroxybenzylidene)benzenesulfonohydrazide

X.-S. Tai, Y.-M. Feng and F.-Y. Kong

Abstract top

There are two molecules in the asymmetric unit of the title compound, C15H16N2O4S, both of which are stabilized by an intramolecular O-H...N hydrogen bond. Intermolecular N-H...O hydrogen bonds lead to [101] chains of molecules in the crystal structure.

Comment top

As part of our ongoing studies of aroylhydrazone ligands (Tai et al., 2003), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

There are two molecules in the asymmetric unit of (I), both of which are stabilised by an intramolecular O-H···N hydrogen bond (Table 1). Then, intermolecular N-H···O hydrogen bonds lead to [101] chains of molecules in the crystal.

Related literature top

For related literature, see: Tai et al. (2003).

Experimental top

3-Ethoxysalicylaldehyde (3 mmol) was added to a solution of benzenesulfonyl hydrazide (3 mmol) in 10 ml of 95% ethanol. The mixture was continuously stirred for 3 h at refluxing temperature, evaporating some ethanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 78%). Colourless blocks of (I) were obtained by evaporation from a methanol solution after 3 days.

Refinement top

The H atoms were placed geometrically (C—H = 0.93–0.96 Å, N—H = 0.90 Å, O-H = 0.82Å) and refined as riding with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl C, O).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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).

Figures top
[Figure 1] Fig. 1. The C1-containing molecule in (I) showing 30% displacement ellipsoids for the non-hydrogen atoms. The intramolecular hydrogen bond is indicated by a double-dashed line.
N'-(3-Ethoxy-2-hydroxybenzylidene)benzenesulfonohydrazide top
Crystal data top
C15H16N2O4SF000 = 1344
Mr = 320.36Dx = 1.345 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3888 reflections
a = 10.3149 (10) Åθ = 2.3–22.4º
b = 39.935 (3) ŵ = 0.22 mm−1
c = 7.9832 (8) ÅT = 298 (2) K
β = 105.773 (2)ºBlock, colourless
V = 3164.7 (5) Å30.48 × 0.45 × 0.32 mm
Z = 8
Data collection top
Bruker SMART CCD
diffractometer		5576 independent reflections
Radiation source: fine-focus sealed tube3515 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.047
T = 298(2) Kθmax = 25.0º
ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −10→12
Tmin = 0.900, Tmax = 0.932k = −47→47
16316 measured reflectionsl = −8→9
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.074H-atom parameters constrained
wR(F2) = 0.160  w = 1/[σ2(Fo2) + (0.0121P)2 + 7.6148P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
5576 reflectionsΔρmax = 0.29 e Å−3
399 parametersΔρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C15H16N2O4SV = 3164.7 (5) Å3
Mr = 320.36Z = 8
Monoclinic, P21/cMo Kα
a = 10.3149 (10) ŵ = 0.22 mm−1
b = 39.935 (3) ÅT = 298 (2) K
c = 7.9832 (8) Å0.48 × 0.45 × 0.32 mm
β = 105.773 (2)º
Data collection top
Bruker SMART CCD
diffractometer		5576 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		3515 reflections with I > 2σ(I)
Tmin = 0.900, Tmax = 0.932Rint = 0.047
16316 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.074399 parameters
wR(F2) = 0.160H-atom parameters constrained
S = 1.09Δρmax = 0.29 e Å−3
5576 reflectionsΔρmin = −0.41 e Å−3
Special details top

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 taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used 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. planes.

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.8862 (4)0.15474 (10)0.5062 (5)0.0505 (10)
H1A0.81900.15910.41020.061*
N20.8858 (4)0.12091 (10)0.5385 (5)0.0457 (10)
N30.4135 (4)0.16102 (10)−0.1714 (5)0.0555 (11)
H30.32710.1542−0.20330.067*
N40.4452 (4)0.16983 (10)0.0019 (5)0.0520 (10)
O11.0083 (3)0.06423 (9)0.6356 (5)0.0632 (10)
H11.00250.08390.60560.095*
O20.9949 (4)0.00231 (10)0.7310 (5)0.0795 (12)
O31.1327 (3)0.16038 (9)0.6246 (4)0.0632 (10)
O40.9990 (4)0.20311 (8)0.4304 (5)0.0704 (11)
O50.6248 (3)0.18032 (8)0.2945 (4)0.0590 (9)
H50.59550.17290.19560.088*
O60.6879 (4)0.20697 (10)0.6006 (5)0.0739 (11)
O70.6420 (3)0.13862 (10)−0.1276 (5)0.0732 (11)
O80.4647 (3)0.12903 (9)−0.4027 (4)0.0628 (10)
S11.02564 (12)0.16900 (3)0.47484 (16)0.0488 (3)
S20.50608 (12)0.13114 (4)−0.21787 (17)0.0560 (4)
C10.7737 (5)0.10720 (13)0.5375 (6)0.0490 (12)
H1C0.69470.11970.50770.059*
C20.7698 (5)0.07232 (13)0.5827 (6)0.0490 (12)
C30.8843 (5)0.05248 (13)0.6323 (6)0.0524 (13)
C40.8766 (6)0.01893 (14)0.6801 (7)0.0643 (15)
C50.7519 (7)0.00549 (16)0.6748 (8)0.084 (2)
H5A0.7448−0.01690.70230.100*
C60.6378 (7)0.02532 (17)0.6289 (9)0.0834 (19)
H60.55500.01620.63010.100*
C70.6444 (5)0.05806 (15)0.5819 (7)0.0646 (15)
H70.56640.07090.54940.078*
C80.9923 (7)−0.03169 (15)0.7840 (10)0.094 (2)
H8A0.9388−0.04510.68880.113*
H8B0.9529−0.03330.88110.113*
C91.1336 (8)−0.04390 (16)0.8364 (10)0.106 (2)
H9A1.1737−0.04070.74220.158*
H9B1.1347−0.06730.86440.158*
H9C1.1839−0.03160.93650.158*
C101.0519 (4)0.14629 (11)0.2984 (6)0.0446 (11)
C110.9513 (5)0.14558 (15)0.1440 (7)0.0672 (16)
H110.86980.15640.13440.081*
C120.9733 (7)0.12869 (19)0.0053 (8)0.093 (2)
H120.90580.1279−0.09910.111*
C131.0929 (7)0.11296 (17)0.0181 (8)0.087 (2)
H131.10650.1014−0.07700.104*
C141.1931 (6)0.11413 (15)0.1711 (8)0.0729 (17)
H141.27520.10370.17910.087*
C151.1724 (5)0.13063 (13)0.3130 (7)0.0567 (13)
H151.23970.13110.41770.068*
C160.3577 (5)0.18495 (12)0.0593 (7)0.0536 (13)
H160.27120.1881−0.01300.064*
C170.3915 (5)0.19724 (11)0.2357 (7)0.0475 (12)
C180.5232 (5)0.19556 (11)0.3449 (6)0.0487 (12)
C190.5557 (5)0.20971 (12)0.5107 (7)0.0543 (13)
C200.4553 (6)0.22539 (13)0.5660 (8)0.0709 (16)
H200.47640.23530.67540.085*
C210.3247 (6)0.22661 (14)0.4621 (9)0.0739 (17)
H210.25760.23650.50310.089*
C220.2943 (5)0.21326 (13)0.2996 (8)0.0651 (16)
H220.20640.21480.22900.078*
C230.7310 (7)0.22377 (17)0.7650 (9)0.094 (2)
H23A0.68640.21420.84640.113*
H23B0.70860.24740.75100.113*
C240.8777 (8)0.21949 (18)0.8307 (9)0.114 (3)
H24A0.89910.19600.83920.171*
H24B0.90860.22960.94370.171*
H24C0.92110.23000.75230.171*
C250.4610 (5)0.09376 (13)−0.1326 (6)0.0530 (13)
C260.3513 (5)0.07603 (15)−0.2264 (8)0.0721 (17)
H260.30040.0840−0.33350.087*
C270.3164 (6)0.04625 (16)−0.1614 (10)0.0851 (19)
H270.24280.0340−0.22540.102*
C280.3898 (8)0.03494 (18)−0.0040 (11)0.091 (2)
H280.36680.01490.03970.109*
C290.4971 (9)0.05293 (19)0.0901 (9)0.098 (2)
H290.54590.04520.19890.118*
C300.5346 (6)0.08246 (16)0.0265 (8)0.0758 (17)
H300.60880.09450.09080.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.034 (2)0.060 (3)0.053 (3)0.0022 (18)0.0051 (18)0.002 (2)
N20.042 (2)0.055 (3)0.040 (2)−0.0004 (18)0.0097 (18)0.0001 (18)
N30.039 (2)0.063 (3)0.057 (3)0.003 (2)0.001 (2)0.000 (2)
N40.042 (2)0.056 (3)0.052 (3)0.002 (2)0.003 (2)0.001 (2)
O10.046 (2)0.064 (2)0.079 (3)−0.0032 (17)0.0152 (18)0.0077 (19)
O20.084 (3)0.061 (2)0.094 (3)−0.002 (2)0.023 (2)0.012 (2)
O30.0392 (18)0.097 (3)0.048 (2)−0.0035 (18)0.0020 (16)−0.0088 (19)
O40.069 (2)0.045 (2)0.100 (3)−0.0005 (18)0.029 (2)−0.001 (2)
O50.051 (2)0.071 (2)0.051 (2)0.0181 (17)0.0067 (17)−0.0066 (17)
O60.075 (3)0.082 (3)0.057 (2)0.013 (2)0.005 (2)−0.020 (2)
O70.0317 (18)0.101 (3)0.079 (3)−0.0013 (19)0.0015 (18)−0.004 (2)
O80.054 (2)0.087 (3)0.045 (2)0.0002 (19)0.0093 (16)0.0056 (18)
S10.0385 (6)0.0533 (8)0.0516 (8)−0.0008 (6)0.0072 (6)−0.0018 (6)
S20.0374 (7)0.0746 (9)0.0517 (8)0.0028 (6)0.0049 (6)0.0025 (7)
C10.037 (3)0.069 (3)0.041 (3)0.003 (2)0.009 (2)0.000 (2)
C20.045 (3)0.063 (3)0.039 (3)−0.012 (2)0.012 (2)−0.007 (2)
C30.055 (3)0.062 (3)0.043 (3)−0.012 (3)0.018 (2)−0.005 (2)
C40.073 (4)0.059 (4)0.063 (4)−0.008 (3)0.021 (3)0.000 (3)
C50.100 (5)0.069 (4)0.092 (5)−0.036 (4)0.044 (4)−0.010 (4)
C60.067 (4)0.094 (5)0.094 (5)−0.036 (4)0.030 (4)−0.016 (4)
C70.055 (3)0.078 (4)0.064 (4)−0.017 (3)0.021 (3)−0.009 (3)
C80.123 (6)0.057 (4)0.113 (6)0.000 (4)0.050 (5)0.006 (4)
C90.135 (7)0.071 (5)0.118 (6)0.023 (4)0.045 (5)0.008 (4)
C100.041 (3)0.049 (3)0.042 (3)−0.004 (2)0.009 (2)0.009 (2)
C110.048 (3)0.092 (4)0.056 (4)0.006 (3)0.004 (3)0.000 (3)
C120.083 (5)0.140 (6)0.050 (4)0.000 (5)0.010 (3)−0.020 (4)
C130.092 (5)0.111 (6)0.065 (4)−0.007 (4)0.034 (4)−0.023 (4)
C140.059 (4)0.079 (4)0.086 (5)0.003 (3)0.028 (3)−0.008 (4)
C150.045 (3)0.070 (3)0.051 (3)0.002 (3)0.008 (2)0.003 (3)
C160.039 (3)0.045 (3)0.074 (4)0.003 (2)0.011 (3)0.011 (3)
C170.042 (3)0.037 (3)0.066 (3)−0.001 (2)0.017 (2)0.004 (2)
C180.051 (3)0.040 (3)0.058 (3)0.008 (2)0.019 (3)0.003 (2)
C190.054 (3)0.045 (3)0.066 (4)0.001 (2)0.018 (3)0.000 (3)
C200.091 (5)0.054 (3)0.078 (4)0.002 (3)0.041 (4)−0.011 (3)
C210.078 (4)0.056 (4)0.104 (5)0.000 (3)0.052 (4)−0.012 (3)
C220.048 (3)0.050 (3)0.103 (5)−0.001 (2)0.031 (3)0.004 (3)
C230.092 (5)0.099 (5)0.082 (5)0.009 (4)0.008 (4)−0.036 (4)
C240.133 (7)0.104 (6)0.084 (5)−0.003 (5)−0.007 (5)−0.032 (4)
C250.042 (3)0.068 (3)0.047 (3)0.017 (2)0.010 (2)0.006 (3)
C260.047 (3)0.084 (4)0.081 (4)0.001 (3)0.010 (3)0.023 (3)
C270.064 (4)0.079 (5)0.116 (6)0.002 (3)0.030 (4)0.018 (4)
C280.104 (6)0.077 (5)0.107 (6)0.024 (4)0.057 (5)0.024 (4)
C290.136 (7)0.093 (6)0.063 (4)0.038 (5)0.024 (5)0.024 (4)
C300.080 (4)0.077 (4)0.061 (4)0.016 (3)0.002 (3)0.000 (3)
Geometric parameters (Å, °) top
N1—N21.375 (5)C10—C151.368 (6)
N1—S11.628 (4)C10—C111.379 (6)
N1—H1A0.8996C11—C121.367 (8)
N2—C11.278 (5)C11—H110.9300
N3—N41.378 (5)C12—C131.363 (8)
N3—S21.633 (4)C12—H120.9300
N3—H30.8998C13—C141.370 (8)
N4—C161.271 (6)C13—H130.9300
O1—C31.355 (5)C14—C151.376 (7)
O1—H10.8187C14—H140.9300
O2—C41.351 (6)C15—H150.9300
O2—C81.425 (6)C16—C171.442 (7)
O3—S11.432 (3)C16—H160.9300
O4—S11.416 (3)C17—C221.398 (7)
O5—C181.364 (5)C17—C181.402 (6)
O5—H50.8202C18—C191.394 (7)
O6—C191.362 (6)C19—C201.381 (7)
O6—C231.433 (6)C20—C211.378 (8)
O7—S21.423 (3)C20—H200.9300
O8—S21.422 (3)C21—C221.358 (8)
S1—C101.757 (5)C21—H210.9300
S2—C251.755 (5)C22—H220.9300
C1—C21.442 (7)C23—C241.470 (9)
C1—H1C0.9300C23—H23A0.9700
C2—C31.388 (7)C23—H23B0.9700
C2—C71.411 (6)C24—H24A0.9600
C3—C41.401 (7)C24—H24B0.9600
C4—C51.384 (8)C24—H24C0.9600
C5—C61.383 (9)C25—C301.368 (7)
C5—H5A0.9300C25—C261.372 (7)
C6—C71.367 (8)C26—C271.384 (8)
C6—H60.9300C26—H260.9300
C7—H70.9300C27—C281.356 (9)
C8—C91.485 (9)C27—H270.9300
C8—H8A0.9700C28—C291.362 (9)
C8—H8B0.9700C28—H280.9300
C9—H9A0.9600C29—C301.380 (9)
C9—H9B0.9600C29—H290.9300
C9—H9C0.9600C30—H300.9300
N2—N1—S1114.8 (3)C13—C12—C11120.9 (6)
N2—N1—H1A108.0C13—C12—H12119.6
S1—N1—H1A108.0C11—C12—H12119.6
C1—N2—N1118.0 (4)C12—C13—C14119.9 (6)
N4—N3—S2114.9 (3)C12—C13—H13120.0
N4—N3—H3107.9C14—C13—H13120.0
S2—N3—H3108.1C13—C14—C15120.2 (6)
C16—N4—N3119.0 (4)C13—C14—H14119.9
C3—O1—H1109.4C15—C14—H14119.9
C4—O2—C8118.0 (5)C10—C15—C14119.3 (5)
C18—O5—H5109.5C10—C15—H15120.4
C19—O6—C23117.5 (4)C14—C15—H15120.4
O4—S1—O3119.6 (2)N4—C16—C17120.4 (4)
O4—S1—N1104.8 (2)N4—C16—H16119.8
O3—S1—N1107.5 (2)C17—C16—H16119.8
O4—S1—C10110.9 (2)C22—C17—C18117.7 (5)
O3—S1—C10107.1 (2)C22—C17—C16120.3 (5)
N1—S1—C10106.1 (2)C18—C17—C16121.8 (4)
O8—S2—O7121.0 (2)O5—C18—C19117.1 (4)
O8—S2—N3104.5 (2)O5—C18—C17122.0 (4)
O7—S2—N3106.7 (2)C19—C18—C17120.9 (5)
O8—S2—C25108.4 (2)O6—C19—C20126.7 (5)
O7—S2—C25108.1 (2)O6—C19—C18114.5 (4)
N3—S2—C25107.5 (2)C20—C19—C18118.7 (5)
N2—C1—C2120.0 (4)C21—C20—C19121.3 (6)
N2—C1—H1C120.0C21—C20—H20119.4
C2—C1—H1C120.0C19—C20—H20119.4
C3—C2—C7118.6 (5)C22—C21—C20119.7 (5)
C3—C2—C1122.9 (4)C22—C21—H21120.2
C7—C2—C1118.5 (5)C20—C21—H21120.2
O1—C3—C2122.2 (5)C21—C22—C17121.7 (5)
O1—C3—C4116.7 (5)C21—C22—H22119.1
C2—C3—C4121.1 (5)C17—C22—H22119.1
O2—C4—C5125.1 (6)O6—C23—C24107.8 (5)
O2—C4—C3116.0 (5)O6—C23—H23A110.1
C5—C4—C3118.9 (6)C24—C23—H23A110.1
C6—C5—C4120.2 (6)O6—C23—H23B110.1
C6—C5—H5A119.9C24—C23—H23B110.1
C4—C5—H5A119.9H23A—C23—H23B108.5
C7—C6—C5121.2 (6)C23—C24—H24A109.5
C7—C6—H6119.4C23—C24—H24B109.5
C5—C6—H6119.4H24A—C24—H24B109.5
C6—C7—C2119.9 (6)C23—C24—H24C109.5
C6—C7—H7120.0H24A—C24—H24C109.5
C2—C7—H7120.0H24B—C24—H24C109.5
O2—C8—C9107.5 (5)C30—C25—C26120.3 (5)
O2—C8—H8A110.2C30—C25—S2120.1 (4)
C9—C8—H8A110.2C26—C25—S2119.6 (4)
O2—C8—H8B110.2C25—C26—C27119.9 (6)
C9—C8—H8B110.2C25—C26—H26120.0
H8A—C8—H8B108.5C27—C26—H26120.0
C8—C9—H9A109.5C28—C27—C26119.8 (7)
C8—C9—H9B109.5C28—C27—H27120.1
H9A—C9—H9B109.5C26—C27—H27120.1
C8—C9—H9C109.5C27—C28—C29120.1 (7)
H9A—C9—H9C109.5C27—C28—H28120.0
H9B—C9—H9C109.5C29—C28—H28120.0
C15—C10—C11120.8 (5)C28—C29—C30121.0 (6)
C15—C10—S1120.1 (4)C28—C29—H29119.5
C11—C10—S1119.0 (4)C30—C29—H29119.5
C12—C11—C10118.9 (5)C25—C30—C29118.9 (6)
C12—C11—H11120.5C25—C30—H30120.6
C10—C11—H11120.5C29—C30—H30120.6
S1—N1—N2—C1−169.4 (3)C12—C13—C14—C151.2 (10)
S2—N3—N4—C16−159.3 (4)C11—C10—C15—C140.3 (8)
N2—N1—S1—O4175.3 (3)S1—C10—C15—C14−177.3 (4)
N2—N1—S1—O3−56.5 (4)C13—C14—C15—C10−1.1 (9)
N2—N1—S1—C1057.8 (4)N3—N4—C16—C17−174.3 (4)
N4—N3—S2—O8−174.1 (3)N4—C16—C17—C22−178.7 (4)
N4—N3—S2—O7−44.9 (4)N4—C16—C17—C185.4 (7)
N4—N3—S2—C2570.9 (4)C22—C17—C18—O5179.7 (4)
N1—N2—C1—C2−175.6 (4)C16—C17—C18—O5−4.3 (7)
N2—C1—C2—C31.6 (7)C22—C17—C18—C19−0.6 (7)
N2—C1—C2—C7179.4 (4)C16—C17—C18—C19175.4 (4)
C7—C2—C3—O1179.6 (4)C23—O6—C19—C20−4.3 (8)
C1—C2—C3—O1−2.5 (7)C23—O6—C19—C18174.1 (5)
C7—C2—C3—C40.3 (7)O5—C18—C19—O61.4 (6)
C1—C2—C3—C4178.1 (5)C17—C18—C19—O6−178.4 (4)
C8—O2—C4—C5−0.1 (9)O5—C18—C19—C20179.9 (4)
C8—O2—C4—C3178.8 (5)C17—C18—C19—C200.1 (7)
O1—C3—C4—O22.5 (7)O6—C19—C20—C21179.7 (5)
C2—C3—C4—O2−178.1 (5)C18—C19—C20—C211.4 (8)
O1—C3—C4—C5−178.5 (5)C19—C20—C21—C22−2.5 (9)
C2—C3—C4—C50.9 (8)C20—C21—C22—C172.1 (8)
O2—C4—C5—C6176.7 (6)C18—C17—C22—C21−0.6 (7)
C3—C4—C5—C6−2.2 (9)C16—C17—C22—C21−176.6 (5)
C4—C5—C6—C72.4 (10)C19—O6—C23—C24−175.7 (5)
C5—C6—C7—C2−1.1 (9)O8—S2—C25—C30151.3 (4)
C3—C2—C7—C6−0.2 (8)O7—S2—C25—C3018.6 (5)
C1—C2—C7—C6−178.1 (5)N3—S2—C25—C30−96.3 (4)
C4—O2—C8—C9−178.9 (5)O8—S2—C25—C26−28.9 (5)
O4—S1—C10—C15119.0 (4)O7—S2—C25—C26−161.7 (4)
O3—S1—C10—C15−13.1 (5)N3—S2—C25—C2683.5 (5)
N1—S1—C10—C15−127.7 (4)C30—C25—C26—C27−1.3 (8)
O4—S1—C10—C11−58.7 (5)S2—C25—C26—C27179.0 (5)
O3—S1—C10—C11169.2 (4)C25—C26—C27—C280.9 (9)
N1—S1—C10—C1154.6 (5)C26—C27—C28—C290.3 (10)
C15—C10—C11—C120.5 (8)C27—C28—C29—C30−1.2 (11)
S1—C10—C11—C12178.2 (5)C26—C25—C30—C290.4 (8)
C10—C11—C12—C13−0.5 (10)S2—C25—C30—C29−179.8 (5)
C11—C12—C13—C14−0.4 (11)C28—C29—C30—C250.8 (10)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.892.606 (5)145
O5—H5···N40.821.872.591 (5)146
N1—H1A···O50.902.142.948 (5)149
N3—H3···O3i0.902.112.912 (5)147
Symmetry codes: (i) x−1, y, z−1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.892.606 (5)145
O5—H5···N40.821.872.591 (5)146
N1—H1A···O50.902.142.948 (5)149
N3—H3···O3i0.902.112.912 (5)147
Symmetry codes: (i) x−1, y, z−1.
Acknowledgements top

The authors thank the National Natural Science Foundation of China (20671073), the National Natural Science Foundation of Shandong, the Science and Technology Foundation of Weifang and Weifang University for research grants.

references
References top

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Tai, X.-S., Yin, X.-H., Tan, M.-Y. & Li, Y.-Z. (2003). Acta Cryst. E59, o681–o682.