organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 10 July 2008; accepted 11 August 2008; online 16 August 2008)

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[Ali, H. M., Laila, M., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1617-o1618.]).

[Scheme 1]

Experimental

Crystal data
  • C15H16N2O3S

  • Mr = 304.36

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.958, Tmax = 0.986

  • 12657 measured reflections

  • 6415 independent reflections

  • 5603 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1o⋯N1 0.84 (3) 1.80 (2) 2.562 (2) 151 (4)
O4—H4o⋯N3 0.85 (3) 1.79 (2) 2.563 (2) 150 (3)
N2—H2n⋯O2i 0.88 (1) 2.18 (1) 3.040 (2) 168 (2)
N4—H4n⋯O5ii 0.88 (1) 2.07 (1) 2.942 (2) 173 (2)
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Comment top

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.).

Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of the asymmetric unit of (I) (Barbour, 2001) at the 70% probability level. Dashed line indicates H-bonding.
N'-[1-(2-Hydroxy-5-methylphenyl)ethylidene]benzenesulfonohydrazide top
Crystal data top
C15H16N2O3SZ = 4
Mr = 304.36F(000) = 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 = 2.2–30.4°
c = 18.2635 (1) ŵ = 0.24 mm1
α = 63.192 (1)°T = 100 K
β = 88.577 (1)°Block, colorless
γ = 86.345 (1)°0.18 × 0.14 × 0.06 mm
V = 1428.19 (4) Å3
Data collection top
Bruker SMART APEX
diffractometer
6415 independent reflections
Radiation source: fine-focus sealed tube5603 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 66
Tmin = 0.958, Tmax = 0.986k = 2222
12657 measured reflectionsl = 2322
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0741P)2 + 1.3P]
where P = (Fo2 + 2Fc2)/3
6415 reflections(Δ/σ)max = 0.001
399 parametersΔρmax = 0.54 e Å3
4 restraintsΔρmin = 0.58 e Å3
Crystal data top
C15H16N2O3Sγ = 86.345 (1)°
Mr = 304.36V = 1428.19 (4) Å3
Triclinic, P1Z = 4
a = 5.1547 (1) ÅMo Kα radiation
b = 17.0321 (2) ŵ = 0.24 mm1
c = 18.2635 (1) ÅT = 100 K
α = 63.192 (1)°0.18 × 0.14 × 0.06 mm
β = 88.577 (1)°
Data collection top
Bruker SMART APEX
diffractometer
6415 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5603 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.986Rint = 0.018
12657 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0424 restraints
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.54 e Å3
6415 reflectionsΔρmin = 0.58 e Å3
399 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
O50.0223 (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)
H300.02400.91380.79030.022*
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) top
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, º) top
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—S1178.55 (13)C12—C13—C14—C150.4 (3)
O3—S1—N2—N1178.10 (12)C11—C10—C15—C140.5 (3)
O2—S1—N2—N148.83 (14)S1—C10—C15—C14179.65 (16)
C10—S1—N2—N166.31 (14)C13—C14—C15—C100.6 (3)
C23—N3—N4—S2178.21 (14)O4—C16—C17—C18179.93 (19)
O6—S2—N4—N3178.19 (12)C21—C16—C17—C180.3 (3)
O5—S2—N4—N353.04 (14)C16—C17—C18—C190.3 (3)
C25—S2—N4—N362.08 (14)C17—C18—C19—C200.2 (3)
O1—C1—C2—C3179.06 (17)C17—C18—C19—C22179.9 (2)
C6—C1—C2—C30.5 (3)C18—C19—C20—C210.4 (3)
C1—C2—C3—C40.2 (3)C22—C19—C20—C21179.54 (19)
C2—C3—C4—C50.4 (3)C19—C20—C21—C160.9 (3)
C2—C3—C4—C7179.82 (18)C19—C20—C21—C23179.97 (18)
C3—C4—C5—C60.8 (3)O4—C16—C21—C20179.57 (18)
C7—C4—C5—C6179.81 (18)C17—C16—C21—C200.8 (3)
C4—C5—C6—C10.5 (3)O4—C16—C21—C230.5 (3)
C4—C5—C6—C8179.50 (17)C17—C16—C21—C23179.88 (18)
O1—C1—C6—C5179.38 (17)N4—N3—C23—C21178.11 (16)
C2—C1—C6—C50.1 (3)N4—N3—C23—C240.7 (3)
O1—C1—C6—C80.6 (3)C20—C21—C23—N3176.27 (18)
C2—C1—C6—C8179.87 (17)C16—C21—C23—N32.8 (3)
N2—N1—C8—C6176.62 (15)C20—C21—C23—C244.9 (3)
N2—N1—C8—C91.1 (3)C16—C21—C23—C24176.08 (18)
C5—C6—C8—N1177.95 (17)O6—S2—C25—C30147.06 (15)
C1—C6—C8—N12.0 (3)O5—S2—C25—C3014.60 (18)
C5—C6—C8—C94.2 (3)N4—S2—C25—C3099.92 (16)
C1—C6—C8—C9175.76 (18)O6—S2—C25—C2631.95 (18)
O3—S1—C10—C15151.83 (16)O5—S2—C25—C26164.42 (15)
O2—S1—C10—C1519.67 (18)N4—S2—C25—C2681.06 (17)
N2—S1—C10—C1595.17 (17)C30—C25—C26—C270.1 (3)
O3—S1—C10—C1128.32 (18)S2—C25—C26—C27178.86 (16)
O2—S1—C10—C11160.48 (15)C25—C26—C27—C281.2 (3)
N2—S1—C10—C1184.68 (16)C26—C27—C28—C291.3 (3)
C15—C10—C11—C120.3 (3)C27—C28—C29—C300.1 (3)
S1—C10—C11—C12179.87 (15)C28—C29—C30—C251.2 (3)
C10—C11—C12—C130.1 (3)C26—C25—C30—C291.3 (3)
C11—C12—C13—C140.2 (3)S2—C25—C30—C29177.65 (15)
Hydrogen-bond geometry (Å, º) top
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) x1, y, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC15H16N2O3S
Mr304.36
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)5.1547 (1), 17.0321 (2), 18.2635 (1)
α, β, γ (°)63.192 (1), 88.577 (1), 86.345 (1)
V3)1428.19 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.18 × 0.14 × 0.06
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.958, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
12657, 6415, 5603
Rint0.018
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.132, 1.05
No. of reflections6415
No. of parameters399
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.54, 0.58

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top
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) x1, y, z; (ii) x+1, y, z.
 

Acknowledgements

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.

References

First citationAli, H. M., Laila, M., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1617–o1618.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds