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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1769.
Published online 2008 August 16. doi:  10.1107/S1600536808025932
PMCID: PMC2960581

N′-[1-(2-Hydr­oxy-5-methyl­phen­yl)ethyl­idene]benzene­sulfonohydrazide

Abstract

The two independent mol­ecules in the asymmetric unit of the title compound, C15H16N2O3S, are each linked by an N—H(...)Osulfon­yl hydrogen bond into a linear chain that runs along the shortest axis of the triclinic unit cell. The hydr­oxy groups are engaged in intra­molecular hydrogen bonding and the amino N atom shows pyramidal coordination.

Related literature

For 2′-(2-hydroxy­phenyl-1-ethyl­idene)benzene­sulfono­hydrazide, which adopts a hydrogen-bonded chain structure, see: Ali et al. (2007 [triangle]).

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Object name is e-64-o1769-scheme1.jpg

Experimental

Crystal data

  • C15H16N2O3S
  • M r = 304.36
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1769-efi1.jpg
  • a = 5.1547 (1) Å
  • b = 17.0321 (2) Å
  • c = 18.2635 (1) Å
  • α = 63.192 (1)°
  • β = 88.577 (1)°
  • γ = 86.345 (1)°
  • V = 1428.19 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 100 (2) K
  • 0.18 × 0.14 × 0.06 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.958, T max = 0.986
  • 12657 measured reflections
  • 6415 independent reflections
  • 5603 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.132
  • S = 1.04
  • 6415 reflections
  • 399 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.54 e Å−3
  • Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025932/bq2092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025932/bq2092Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Science Fund (12–02-03–2031, 12–02-03–2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

2'-(2-Hydroxyphenyl-1-ethylidene)benzenesulfonohydrazide adopts a hydrogen-bonded chain structure; the chain runs along the a-axis of the monoclinic unit cell and the repeat distance is the length of the this axis, i.e., 5.18 Å (Ali et al., 2007). An additional methyl group in the molecule (Scheme I) does not result in any significant difference in both structure and packing (Fig. 1). The two independent molecules are each linked by an NH···O sulfonyl hydrogen-bond into a linear chain that runs along the shortest axis of the triclinic unit cell; the repeat distance is 5.15 Å. The hydroxy groups are engaged in intramolecular hydrogen bonding (Table 1.).

Experimental

The Schiff base was prepared by refluxing by benzene sulfanohydrazide (0.40 g, 0.64 mmol) and 5-methyl-2-hydroxyacetophenone (0.10 g, 0.64 mmol) in ethanol for 2 h. The product was filtered and recrystallized from ethanol.

Refinement

Carbon-bound hydrogen atoms were generated geometrically (C—H 0.95 to 98 Å), and were treated as riding, with U(H) 1.2 to 1.5 times Ueq(C). The amino and hydroxy H-atoms were located in a difference Fourier map, and were refined with distance restraints (N–H 0.88±0.01, O–H 0.84±0.01 Å); their temperature factors were freely refined.

Figures

Fig. 1.
Thermal ellipsoid plot of the asymmetric unit of (I) (Barbour, 2001) at the 70% probability level. Dashed line indicates H-bonding.

Crystal data

C15H16N2O3SZ = 4
Mr = 304.36F000 = 640
Triclinic, P1Dx = 1.415 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 5.1547 (1) ÅCell parameters from 7775 reflections
b = 17.0321 (2) Åθ = 2.2–30.4º
c = 18.2635 (1) ŵ = 0.24 mm1
α = 63.192 (1)ºT = 100 (2) K
β = 88.577 (1)ºBlock, colorless
γ = 86.345 (1)º0.18 × 0.14 × 0.06 mm
V = 1428.19 (4) Å3

Data collection

Bruker SMART APEX diffractometer6415 independent reflections
Radiation source: fine-focus sealed tube5603 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.018
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.3º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −6→6
Tmin = 0.958, Tmax = 0.986k = −22→22
12657 measured reflectionsl = −23→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132  w = 1/[σ2(Fo2) + (0.0741P)2 + 1.3P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
6415 reflectionsΔρmax = 0.54 e Å3
399 parametersΔρmin = −0.58 e Å3
4 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S11.00270 (8)0.59346 (3)0.36837 (3)0.01389 (12)
S20.23309 (8)0.87206 (3)0.94073 (3)0.01512 (12)
O11.1834 (3)0.79133 (9)0.43334 (9)0.0198 (3)
O21.2673 (3)0.59821 (9)0.38815 (8)0.0181 (3)
O30.9214 (3)0.51803 (9)0.36199 (9)0.0190 (3)
O40.1038 (3)0.73122 (10)0.80833 (9)0.0238 (3)
O5−0.0223 (3)0.84056 (10)0.94695 (9)0.0206 (3)
O60.3106 (3)0.90879 (9)0.99282 (9)0.0196 (3)
N10.8800 (3)0.66835 (10)0.45822 (10)0.0153 (3)
N20.8209 (3)0.59890 (11)0.44147 (10)0.0150 (3)
N30.3956 (3)0.74366 (11)0.91380 (10)0.0163 (3)
N40.4405 (3)0.78638 (11)0.96235 (10)0.0159 (3)
C11.0427 (4)0.80153 (13)0.49302 (12)0.0165 (4)
C21.1112 (4)0.86743 (13)0.51253 (13)0.0200 (4)
H21.25250.90230.48510.024*
C30.9752 (4)0.88270 (13)0.57162 (13)0.0205 (4)
H31.02440.92820.58400.025*
C40.7677 (4)0.83279 (13)0.61327 (12)0.0189 (4)
C50.7016 (4)0.76637 (13)0.59405 (12)0.0173 (4)
H50.56170.73130.62250.021*
C60.8335 (4)0.74898 (12)0.53418 (11)0.0151 (4)
C70.6197 (4)0.84927 (15)0.67793 (14)0.0243 (4)
H7A0.43820.83510.67830.037*
H7B0.62640.91140.66560.037*
H7C0.69850.81200.73180.037*
C80.7526 (4)0.67782 (12)0.51600 (11)0.0152 (4)
C90.5429 (4)0.61962 (13)0.56463 (13)0.0208 (4)
H9A0.49090.58470.53760.031*
H9B0.39260.65590.56820.031*
H9C0.60770.58000.61990.031*
C100.9242 (4)0.68803 (12)0.27615 (11)0.0153 (4)
C110.7132 (4)0.68724 (14)0.23050 (12)0.0200 (4)
H110.61390.63670.24890.024*
C120.6499 (4)0.76133 (14)0.15765 (12)0.0219 (4)
H120.50650.76160.12580.026*
C130.7956 (4)0.83520 (14)0.13098 (12)0.0224 (4)
H130.75120.88590.08110.027*
C141.0053 (4)0.83500 (14)0.17703 (13)0.0242 (4)
H141.10500.88550.15840.029*
C151.0708 (4)0.76134 (14)0.25038 (12)0.0206 (4)
H151.21360.76120.28230.025*
C160.2653 (4)0.66099 (14)0.81883 (12)0.0194 (4)
C170.2155 (4)0.61764 (15)0.77206 (13)0.0230 (4)
H170.07300.63800.73480.028*
C180.3706 (4)0.54571 (14)0.77928 (13)0.0222 (4)
H180.33280.51700.74700.027*
C190.5829 (4)0.51392 (14)0.83316 (13)0.0209 (4)
C200.6317 (4)0.55738 (13)0.87953 (12)0.0189 (4)
H200.77590.53670.91610.023*
C210.4775 (4)0.63059 (13)0.87480 (12)0.0171 (4)
C220.7530 (4)0.43515 (15)0.84084 (15)0.0273 (5)
H22A0.92310.43640.86300.041*
H22B0.77530.43690.78670.041*
H22C0.67090.38100.87790.041*
C230.5394 (4)0.67411 (13)0.92575 (11)0.0162 (4)
C240.7550 (4)0.63615 (13)0.98790 (12)0.0196 (4)
H24A0.74880.66601.02290.029*
H24B0.92260.64460.95960.029*
H24C0.73440.57311.02170.029*
C250.2788 (4)0.94842 (12)0.83776 (11)0.0157 (4)
C260.4827 (4)1.00410 (13)0.81963 (13)0.0202 (4)
H260.59541.00000.86170.024*
C270.5177 (4)1.06564 (14)0.73883 (13)0.0225 (4)
H270.65771.10340.72510.027*
C280.3492 (4)1.07231 (13)0.67788 (13)0.0210 (4)
H280.37211.11540.62290.025*
C290.1478 (4)1.01618 (14)0.69714 (13)0.0215 (4)
H290.03331.02100.65510.026*
C300.1120 (4)0.95307 (13)0.77718 (12)0.0185 (4)
H30−0.02400.91380.79030.022*
H1O1.110 (6)0.7524 (18)0.427 (2)0.057 (10)*
H4O0.165 (6)0.752 (2)0.8385 (17)0.043 (8)*
H2N0.657 (2)0.5927 (17)0.4337 (16)0.025 (6)*
H4N0.600 (2)0.8017 (16)0.9621 (16)0.022 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0143 (2)0.0138 (2)0.0141 (2)−0.00056 (16)−0.00083 (16)−0.00670 (17)
S20.0133 (2)0.0169 (2)0.0150 (2)−0.00203 (16)−0.00012 (16)−0.00687 (18)
O10.0216 (7)0.0193 (7)0.0200 (7)−0.0062 (6)0.0044 (5)−0.0098 (6)
O20.0157 (6)0.0183 (7)0.0186 (7)−0.0004 (5)−0.0014 (5)−0.0068 (6)
O30.0213 (7)0.0173 (7)0.0206 (7)−0.0016 (5)−0.0016 (5)−0.0103 (6)
O40.0222 (7)0.0268 (8)0.0248 (8)0.0032 (6)−0.0080 (6)−0.0140 (7)
O50.0145 (6)0.0248 (7)0.0205 (7)−0.0042 (5)0.0008 (5)−0.0080 (6)
O60.0217 (7)0.0225 (7)0.0175 (7)−0.0013 (6)−0.0007 (5)−0.0117 (6)
N10.0181 (8)0.0142 (7)0.0152 (7)−0.0022 (6)−0.0020 (6)−0.0078 (6)
N20.0160 (7)0.0160 (8)0.0157 (7)−0.0036 (6)0.0015 (6)−0.0091 (6)
N30.0169 (7)0.0173 (8)0.0162 (8)−0.0034 (6)−0.0004 (6)−0.0084 (6)
N40.0152 (7)0.0167 (8)0.0166 (8)−0.0014 (6)−0.0026 (6)−0.0080 (6)
C10.0182 (9)0.0153 (9)0.0140 (8)0.0000 (7)−0.0023 (7)−0.0049 (7)
C20.0217 (9)0.0157 (9)0.0205 (9)−0.0026 (7)−0.0030 (7)−0.0060 (8)
C30.0239 (10)0.0169 (9)0.0230 (10)0.0006 (7)−0.0065 (8)−0.0110 (8)
C40.0207 (9)0.0191 (9)0.0175 (9)0.0042 (7)−0.0052 (7)−0.0093 (8)
C50.0178 (9)0.0168 (9)0.0170 (9)0.0005 (7)−0.0023 (7)−0.0074 (7)
C60.0182 (9)0.0131 (8)0.0132 (8)0.0004 (7)−0.0028 (7)−0.0053 (7)
C70.0257 (10)0.0265 (11)0.0271 (11)0.0034 (8)−0.0021 (8)−0.0181 (9)
C80.0164 (8)0.0135 (8)0.0132 (8)0.0003 (7)−0.0024 (7)−0.0039 (7)
C90.0233 (10)0.0181 (9)0.0222 (10)−0.0051 (8)0.0081 (8)−0.0102 (8)
C100.0165 (8)0.0164 (9)0.0127 (8)−0.0003 (7)0.0000 (7)−0.0064 (7)
C110.0212 (9)0.0202 (10)0.0191 (9)−0.0035 (7)−0.0014 (7)−0.0091 (8)
C120.0230 (10)0.0260 (10)0.0169 (9)0.0012 (8)−0.0050 (7)−0.0101 (8)
C130.0272 (10)0.0219 (10)0.0145 (9)0.0026 (8)0.0006 (8)−0.0057 (8)
C140.0290 (11)0.0181 (10)0.0225 (10)−0.0055 (8)−0.0002 (8)−0.0061 (8)
C150.0217 (9)0.0210 (10)0.0189 (9)−0.0029 (8)−0.0018 (7)−0.0086 (8)
C160.0186 (9)0.0218 (10)0.0176 (9)−0.0035 (7)0.0003 (7)−0.0085 (8)
C170.0219 (10)0.0283 (11)0.0197 (10)−0.0052 (8)−0.0019 (8)−0.0111 (9)
C180.0270 (10)0.0257 (10)0.0177 (9)−0.0087 (8)0.0045 (8)−0.0124 (8)
C190.0213 (9)0.0221 (10)0.0208 (10)−0.0073 (8)0.0050 (8)−0.0105 (8)
C200.0197 (9)0.0197 (9)0.0181 (9)−0.0039 (7)0.0011 (7)−0.0091 (8)
C210.0177 (9)0.0190 (9)0.0157 (9)−0.0050 (7)0.0017 (7)−0.0083 (8)
C220.0288 (11)0.0269 (11)0.0325 (12)−0.0031 (9)0.0015 (9)−0.0188 (10)
C230.0161 (9)0.0169 (9)0.0138 (8)−0.0040 (7)0.0009 (7)−0.0049 (7)
C240.0206 (9)0.0177 (9)0.0191 (9)−0.0008 (7)−0.0034 (7)−0.0070 (8)
C250.0167 (9)0.0146 (8)0.0136 (8)0.0002 (7)0.0003 (7)−0.0047 (7)
C260.0182 (9)0.0200 (9)0.0209 (10)−0.0019 (7)−0.0025 (7)−0.0075 (8)
C270.0191 (9)0.0174 (9)0.0262 (11)−0.0029 (7)0.0015 (8)−0.0054 (8)
C280.0235 (10)0.0184 (9)0.0180 (9)0.0028 (8)0.0017 (7)−0.0060 (8)
C290.0243 (10)0.0233 (10)0.0188 (9)0.0019 (8)−0.0038 (8)−0.0115 (8)
C300.0184 (9)0.0195 (9)0.0192 (9)−0.0012 (7)−0.0018 (7)−0.0099 (8)

Geometric parameters (Å, °)

S1—O31.4303 (14)C11—C121.387 (3)
S1—O21.4360 (14)C11—H110.9500
S1—N21.6455 (16)C12—C131.390 (3)
S1—C101.7603 (19)C12—H120.9500
S2—O61.4296 (14)C13—C141.385 (3)
S2—O51.4355 (14)C13—H130.9500
S2—N41.6526 (17)C14—C151.391 (3)
S2—C251.7591 (19)C14—H140.9500
O1—C11.364 (2)C15—H150.9500
O1—H1O0.84 (3)C16—C171.394 (3)
O4—C161.355 (2)C16—C211.419 (3)
O4—H4O0.85 (3)C17—C181.376 (3)
N1—C81.295 (2)C17—H170.9500
N1—N21.401 (2)C18—C191.399 (3)
N2—H2N0.879 (10)C18—H180.9500
N3—C231.290 (3)C19—C201.389 (3)
N3—N41.408 (2)C19—C221.508 (3)
N4—H4N0.877 (10)C20—C211.405 (3)
C1—C21.389 (3)C20—H200.9500
C1—C61.416 (3)C21—C231.478 (3)
C2—C31.384 (3)C22—H22A0.9800
C2—H20.9500C22—H22B0.9800
C3—C41.392 (3)C22—H22C0.9800
C3—H30.9500C23—C241.500 (3)
C4—C51.390 (3)C24—H24A0.9800
C4—C71.511 (3)C24—H24B0.9800
C5—C61.406 (3)C24—H24C0.9800
C5—H50.9500C25—C301.389 (3)
C6—C81.479 (2)C25—C261.393 (3)
C7—H7A0.9800C26—C271.387 (3)
C7—H7B0.9800C26—H260.9500
C7—H7C0.9800C27—C281.388 (3)
C8—C91.495 (3)C27—H270.9500
C9—H9A0.9800C28—C291.386 (3)
C9—H9B0.9800C28—H280.9500
C9—H9C0.9800C29—C301.386 (3)
C10—C151.387 (3)C29—H290.9500
C10—C111.391 (3)C30—H300.9500
O3—S1—O2120.83 (8)C11—C12—H12119.9
O3—S1—N2104.70 (8)C13—C12—H12119.9
O2—S1—N2106.84 (8)C14—C13—C12120.07 (19)
O3—S1—C10108.61 (9)C14—C13—H13120.0
O2—S1—C10107.30 (9)C12—C13—H13120.0
N2—S1—C10107.97 (9)C13—C14—C15120.38 (19)
O6—S2—O5120.70 (9)C13—C14—H14119.8
O6—S2—N4104.46 (8)C15—C14—H14119.8
O5—S2—N4106.50 (9)C10—C15—C14118.93 (18)
O6—S2—C25109.14 (9)C10—C15—H15120.5
O5—S2—C25107.40 (9)C14—C15—H15120.5
N4—S2—C25108.03 (9)O4—C16—C17117.22 (18)
C1—O1—H1O104 (3)O4—C16—C21122.92 (17)
C16—O4—H4O105 (2)C17—C16—C21119.85 (19)
C8—N1—N2118.12 (16)C18—C17—C16120.71 (19)
N1—N2—S1112.74 (12)C18—C17—H17119.6
N1—N2—H2N118.6 (17)C16—C17—H17119.6
S1—N2—H2N110.1 (17)C17—C18—C19121.38 (18)
C23—N3—N4118.41 (16)C17—C18—H18119.3
N3—N4—S2111.80 (12)C19—C18—H18119.3
N3—N4—H4N115.8 (17)C20—C19—C18117.66 (19)
S2—N4—H4N110.0 (17)C20—C19—C22121.06 (19)
O1—C1—C2117.07 (17)C18—C19—C22121.29 (18)
O1—C1—C6123.00 (17)C19—C20—C21123.01 (18)
C2—C1—C6119.92 (18)C19—C20—H20118.5
C3—C2—C1120.50 (19)C21—C20—H20118.5
C3—C2—H2119.8C20—C21—C16117.39 (17)
C1—C2—H2119.8C20—C21—C23120.48 (17)
C2—C3—C4121.39 (18)C16—C21—C23122.13 (18)
C2—C3—H3119.3C19—C22—H22A109.5
C4—C3—H3119.3C19—C22—H22B109.5
C5—C4—C3117.86 (18)H22A—C22—H22B109.5
C5—C4—C7120.74 (19)C19—C22—H22C109.5
C3—C4—C7121.40 (18)H22A—C22—H22C109.5
C4—C5—C6122.59 (19)H22B—C22—H22C109.5
C4—C5—H5118.7N3—C23—C21115.90 (17)
C6—C5—H5118.7N3—C23—C24123.93 (17)
C5—C6—C1117.73 (17)C21—C23—C24120.16 (17)
C5—C6—C8120.05 (17)C23—C24—H24A109.5
C1—C6—C8122.22 (17)C23—C24—H24B109.5
C4—C7—H7A109.5H24A—C24—H24B109.5
C4—C7—H7B109.5C23—C24—H24C109.5
H7A—C7—H7B109.5H24A—C24—H24C109.5
C4—C7—H7C109.5H24B—C24—H24C109.5
H7A—C7—H7C109.5C30—C25—C26121.68 (18)
H7B—C7—H7C109.5C30—C25—S2120.18 (15)
N1—C8—C6115.73 (17)C26—C25—S2118.14 (15)
N1—C8—C9123.48 (17)C27—C26—C25118.62 (18)
C6—C8—C9120.75 (16)C27—C26—H26120.7
C8—C9—H9A109.5C25—C26—H26120.7
C8—C9—H9B109.5C26—C27—C28120.36 (19)
H9A—C9—H9B109.5C26—C27—H27119.8
C8—C9—H9C109.5C28—C27—H27119.8
H9A—C9—H9C109.5C29—C28—C27120.14 (19)
H9B—C9—H9C109.5C29—C28—H28119.9
C15—C10—C11121.32 (18)C27—C28—H28119.9
C15—C10—S1120.15 (14)C30—C29—C28120.52 (19)
C11—C10—S1118.53 (15)C30—C29—H29119.7
C12—C11—C10119.01 (19)C28—C29—H29119.7
C12—C11—H11120.5C29—C30—C25118.66 (18)
C10—C11—H11120.5C29—C30—H30120.7
C11—C12—C13120.27 (18)C25—C30—H30120.7
C8—N1—N2—S1−178.55 (13)C12—C13—C14—C15−0.4 (3)
O3—S1—N2—N1178.10 (12)C11—C10—C15—C14−0.5 (3)
O2—S1—N2—N148.83 (14)S1—C10—C15—C14179.65 (16)
C10—S1—N2—N1−66.31 (14)C13—C14—C15—C100.6 (3)
C23—N3—N4—S2−178.21 (14)O4—C16—C17—C18−179.93 (19)
O6—S2—N4—N3−178.19 (12)C21—C16—C17—C18−0.3 (3)
O5—S2—N4—N353.04 (14)C16—C17—C18—C19−0.3 (3)
C25—S2—N4—N3−62.08 (14)C17—C18—C19—C200.2 (3)
O1—C1—C2—C3179.06 (17)C17—C18—C19—C22−179.9 (2)
C6—C1—C2—C3−0.5 (3)C18—C19—C20—C210.4 (3)
C1—C2—C3—C40.2 (3)C22—C19—C20—C21−179.54 (19)
C2—C3—C4—C50.4 (3)C19—C20—C21—C16−0.9 (3)
C2—C3—C4—C7179.82 (18)C19—C20—C21—C23−179.97 (18)
C3—C4—C5—C6−0.8 (3)O4—C16—C21—C20−179.57 (18)
C7—C4—C5—C6179.81 (18)C17—C16—C21—C200.8 (3)
C4—C5—C6—C10.5 (3)O4—C16—C21—C23−0.5 (3)
C4—C5—C6—C8−179.50 (17)C17—C16—C21—C23179.88 (18)
O1—C1—C6—C5−179.38 (17)N4—N3—C23—C21178.11 (16)
C2—C1—C6—C50.1 (3)N4—N3—C23—C24−0.7 (3)
O1—C1—C6—C80.6 (3)C20—C21—C23—N3176.27 (18)
C2—C1—C6—C8−179.87 (17)C16—C21—C23—N3−2.8 (3)
N2—N1—C8—C6176.62 (15)C20—C21—C23—C24−4.9 (3)
N2—N1—C8—C9−1.1 (3)C16—C21—C23—C24176.08 (18)
C5—C6—C8—N1177.95 (17)O6—S2—C25—C30−147.06 (15)
C1—C6—C8—N1−2.0 (3)O5—S2—C25—C30−14.60 (18)
C5—C6—C8—C9−4.2 (3)N4—S2—C25—C3099.92 (16)
C1—C6—C8—C9175.76 (18)O6—S2—C25—C2631.95 (18)
O3—S1—C10—C15−151.83 (16)O5—S2—C25—C26164.42 (15)
O2—S1—C10—C15−19.67 (18)N4—S2—C25—C26−81.06 (17)
N2—S1—C10—C1595.17 (17)C30—C25—C26—C270.1 (3)
O3—S1—C10—C1128.32 (18)S2—C25—C26—C27−178.86 (16)
O2—S1—C10—C11160.48 (15)C25—C26—C27—C281.2 (3)
N2—S1—C10—C11−84.68 (16)C26—C27—C28—C29−1.3 (3)
C15—C10—C11—C120.3 (3)C27—C28—C29—C300.1 (3)
S1—C10—C11—C12−179.87 (15)C28—C29—C30—C251.2 (3)
C10—C11—C12—C13−0.1 (3)C26—C25—C30—C29−1.3 (3)
C11—C12—C13—C140.2 (3)S2—C25—C30—C29177.65 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1o···N10.84 (3)1.80 (2)2.562 (2)151 (4)
O4—H4o···N30.85 (3)1.79 (2)2.563 (2)150 (3)
N2—H2n···O2i0.88 (1)2.18 (1)3.040 (2)168 (2)
N4—H4n···O5ii0.88 (1)2.07 (1)2.942 (2)173 (2)

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2092).

References

  • Ali, H. M., Laila, M., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1617–o1618.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

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