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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
Musalem Laila,a Hapipah M. Ali,a Subramaniam Puvaneswary,a Ward T. Robinson,a and Seik Weng Nga*
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng/at/um.edu.my
Received July 10, 2008; Accepted August 11, 2008.
Abstract
The two independent mol­ecules in the asymmetric unit of the title compound, C15H16N2O3S, are each linked by an N—H[cdots, three dots, centered]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 Object name is e-64-o1769-scheme1.jpg
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
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.
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.
 
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2092).
References
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  • 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.
  • Westrip, S. P. (2008). publCIF In preparation.

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