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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o923.
Published online 2008 April 26. doi:  10.1107/S1600536808011628
PMCID: PMC2961336

Diethyl 5-[(2-hydr­oxy-1-naphth­yl)methyl­ideneamino]-3-methyl­thio­phene-2,4-dicarboxyl­ate

Abstract

In the title compound, C22H21NO5S, the 2-naphthol group and the thio­phene ring are almost coplanar, with a dihedral angle of 5.75 (7)°. The structure is stabilized by intra­molecular O—H(...)O, O—H(...)N and C—H(...)S, and inter­molecular C—H(...)O hydrogen-bonding inter­actions.

Related literature

For related structures, see: Akkurt, Karaca et al. (2008 [triangle]); Akkurt, Yıldırım et al. (2008 [triangle]); Asiri & Badahdah (2007 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o923-scheme1.jpg

Experimental

Crystal data

  • C22H21NO5S
  • M r = 411.47
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o923-efi1.jpg
  • a = 8.7111 (4) Å
  • b = 11.5319 (5) Å
  • c = 11.9778 (5) Å
  • α = 61.594 (3)°
  • β = 79.489 (3)°
  • γ = 89.334 (3)°
  • V = 1036.67 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 293 (2) K
  • 0.63 × 0.38 × 0.10 mm

Data collection

  • Stoe IPDS-2 diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie) T min = 0.890, T max = 0.981
  • 18909 measured reflections
  • 4047 independent reflections
  • 3397 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.111
  • S = 1.06
  • 4047 reflections
  • 265 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011628/sj2483sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011628/sj2483Isup2.hkl

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-2 diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

We recently reported the structures of 4-[(2-hydroxy-1-naphthyl)methylideneamino]benzoic acid (Akkurt, Yıldırım et al., 2008) and 2-[(2-Hydroxybenzylidene) amino]-3-methoxycarbonyl-3,4,5,6-tetrahydrobenzo[d] thiophene (Akkurt, Karaca et al., 2008). In this communication, we report the structure of the title compound, 4-[(2-hydroxynaphth-1-yl methylidene) amino]-3,5-diethoxycarbonyl- 4-methylthiophene (I), as a part of an ongoing investigation into the development of anil derivatives.

In the title compound (Fig. 1), all values of the geometric parameters are normal (Allen et al., 1987). The naphthalen-2-ol group and thiophene ring are each almost planar, with maximum deviations of -0.020 (1) Å for O1 and 0.008 (2) Å for C15, respectively, and the respective ring planes are oriented with a dihedral angle of 5.75 (7)° between them. Intramolecular O1—H1A···O3, O1—H1A···N1 and C1—H1···S hydrogen bonds effect this conformation and the structure is further stabilised by intermolecular C—H···O hydrogen bonding interactions (Table 1 and Fig. 2).

Experimental

The title compound, I, was prepared by the method of Asiri & Badahdah (2007) and recrystallised from ethanol. [Yield 99%, mp: 448 K].

Refinement

The H atoms were positioned geometrically (C—H = 0.93 - 0.97 Å, O—H = 0.82 Å) and refined as riding with with Uiso(H) = 1.2Ueq(Caromatic, Cmethylene) and 1.5Ueq(Cmethyl,Ohydroxyl).

Figures

Fig. 1.
A view of the title compound, I, with the atom-numbering scheme, and 30% probability displacement ellipsoids. Classical intramolecular H-bonds are drawn as dashed lines.
Fig. 2.
The crystal packing of I with hydrogen bonds drawn as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C22H21NO5SZ = 2
Mr = 411.47F000 = 432
Triclinic, P1Dx = 1.318 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.7111 (4) ÅCell parameters from 18909 reflections
b = 11.5319 (5) Åθ = 2.0–28.0º
c = 11.9778 (5) ŵ = 0.19 mm1
α = 61.594 (3)ºT = 293 (2) K
β = 79.489 (3)ºPlate, orange
γ = 89.334 (3)º0.63 × 0.38 × 0.10 mm
V = 1036.67 (9) Å3

Data collection

Stoe IPDS-2 diffractometer4047 independent reflections
Monochromator: plane graphite3397 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.029
T = 293(2) Kθmax = 26.0º
ω scansθmin = 2.0º
Absorption correction: integration(X-RED32; Stoe & Cie)h = −10→10
Tmin = 0.890, Tmax = 0.981k = −14→14
18909 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.111  w = 1/[σ2(Fo2) + (0.064P)2 + 0.1098P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
4047 reflectionsΔρmax = 0.29 e Å3
265 parametersΔρmin = −0.15 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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)

xyzUiso*/Ueq
S10.49573 (5)0.76909 (4)0.39643 (4)0.0501 (1)
O10.14230 (15)0.32467 (13)0.72848 (10)0.0600 (4)
O20.3809 (2)0.60637 (15)0.86430 (13)0.0796 (6)
O30.40230 (17)0.44308 (13)0.81405 (11)0.0629 (4)
O40.7590 (2)1.03239 (15)0.40759 (16)0.0874 (6)
O50.70559 (18)0.99593 (13)0.25144 (13)0.0721 (5)
N10.31832 (15)0.53737 (13)0.57083 (12)0.0454 (4)
C10.27937 (17)0.52740 (15)0.47657 (14)0.0433 (4)
C20.17178 (17)0.42282 (15)0.49800 (14)0.0421 (4)
C30.10639 (19)0.32652 (16)0.62436 (15)0.0488 (5)
C4−0.0033 (2)0.22477 (18)0.64652 (17)0.0576 (5)
C5−0.0463 (2)0.21932 (18)0.54624 (18)0.0576 (5)
C60.01516 (18)0.31457 (16)0.41623 (16)0.0485 (5)
C7−0.0334 (2)0.30932 (19)0.31243 (19)0.0599 (6)
C80.0266 (2)0.4000 (2)0.18768 (19)0.0648 (7)
C90.1389 (2)0.4991 (2)0.16108 (17)0.0613 (6)
C100.1874 (2)0.50831 (17)0.25911 (15)0.0517 (5)
C110.12654 (17)0.41718 (15)0.39031 (14)0.0431 (4)
C120.41757 (18)0.64162 (15)0.54888 (14)0.0440 (5)
C130.46275 (18)0.66050 (16)0.64435 (15)0.0460 (5)
C140.56177 (19)0.77890 (16)0.59411 (16)0.0491 (5)
C150.59028 (19)0.84540 (16)0.46218 (17)0.0504 (5)
C160.6309 (2)0.8209 (2)0.6770 (2)0.0646 (7)
C170.4107 (2)0.56996 (18)0.78467 (16)0.0545 (6)
C180.3541 (4)0.3472 (2)0.9500 (2)0.0952 (9)
C190.3661 (5)0.2151 (3)0.9659 (3)0.1222 (16)
C200.6929 (2)0.96689 (18)0.37492 (19)0.0595 (6)
C210.8094 (3)1.1108 (2)0.1560 (2)0.0924 (9)
C220.8308 (5)1.1111 (3)0.0332 (3)0.1284 (13)
H10.322800.590400.391900.0520*
H1A0.206500.387100.705700.0900*
H4−0.046300.161000.731000.0690*
H5−0.118200.151200.563100.0690*
H7−0.107800.242600.329900.0720*
H8−0.007200.395800.120300.0780*
H90.181600.560000.075500.0730*
H100.262000.576000.239000.0620*
H16A0.678600.748200.737200.0970*
H16B0.549500.847300.723800.0970*
H16C0.708600.894000.622900.0970*
H18A0.420600.361700.999800.1140*
H18B0.246800.357300.981700.1140*
H19A0.339700.151501.056400.1830*
H19B0.471300.206900.930800.1830*
H19C0.295100.199300.921000.1830*
H21A0.909601.107300.181500.1110*
H21B0.764401.190800.148600.1110*
H22A0.910401.17940−0.028800.1920*
H22B0.734001.127300.002800.1920*
H22C0.862101.026800.044200.1920*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0542 (2)0.0489 (2)0.0479 (2)−0.0031 (2)−0.0107 (2)−0.0236 (2)
O10.0637 (8)0.0669 (8)0.0435 (6)−0.0065 (6)−0.0077 (5)−0.0228 (5)
O20.1077 (12)0.0840 (10)0.0569 (7)−0.0006 (9)−0.0050 (7)−0.0456 (7)
O30.0824 (9)0.0577 (7)0.0464 (6)−0.0033 (6)−0.0131 (6)−0.0232 (5)
O40.1040 (12)0.0666 (9)0.0921 (11)−0.0283 (8)−0.0127 (9)−0.0402 (8)
O50.0825 (10)0.0542 (7)0.0677 (8)−0.0158 (7)−0.0004 (7)−0.0246 (6)
N10.0443 (7)0.0495 (7)0.0475 (7)0.0003 (6)−0.0099 (5)−0.0270 (6)
C10.0424 (8)0.0458 (8)0.0438 (7)0.0014 (6)−0.0079 (6)−0.0234 (6)
C20.0380 (7)0.0451 (8)0.0457 (7)0.0024 (6)−0.0078 (6)−0.0240 (6)
C30.0447 (8)0.0520 (9)0.0481 (8)0.0033 (7)−0.0074 (6)−0.0236 (7)
C40.0533 (10)0.0517 (9)0.0542 (9)−0.0063 (7)−0.0023 (7)−0.0174 (8)
C50.0476 (9)0.0517 (9)0.0710 (10)−0.0073 (7)−0.0068 (8)−0.0291 (8)
C60.0413 (8)0.0500 (9)0.0604 (9)0.0019 (7)−0.0104 (7)−0.0313 (8)
C70.0524 (10)0.0669 (11)0.0770 (12)−0.0012 (8)−0.0186 (8)−0.0459 (10)
C80.0705 (12)0.0781 (13)0.0631 (11)0.0009 (10)−0.0218 (9)−0.0447 (10)
C90.0693 (12)0.0675 (11)0.0502 (9)−0.0004 (9)−0.0131 (8)−0.0303 (8)
C100.0546 (9)0.0548 (9)0.0484 (8)−0.0041 (7)−0.0087 (7)−0.0273 (7)
C110.0382 (7)0.0459 (8)0.0514 (8)0.0037 (6)−0.0099 (6)−0.0281 (7)
C120.0408 (8)0.0466 (8)0.0491 (8)0.0033 (6)−0.0097 (6)−0.0265 (7)
C130.0434 (8)0.0513 (8)0.0511 (8)0.0048 (7)−0.0107 (6)−0.0305 (7)
C140.0470 (8)0.0513 (9)0.0608 (9)0.0061 (7)−0.0149 (7)−0.0350 (8)
C150.0479 (9)0.0466 (8)0.0643 (10)0.0032 (7)−0.0131 (7)−0.0321 (8)
C160.0669 (11)0.0694 (12)0.0754 (12)−0.0004 (9)−0.0208 (9)−0.0468 (10)
C170.0555 (10)0.0647 (11)0.0516 (9)0.0015 (8)−0.0124 (7)−0.0340 (8)
C180.144 (2)0.0779 (15)0.0481 (10)−0.0184 (15)−0.0121 (12)−0.0198 (10)
C190.186 (4)0.0726 (17)0.0824 (17)−0.0039 (19)−0.0425 (19)−0.0114 (13)
C200.0577 (10)0.0493 (9)0.0721 (11)0.0000 (8)−0.0081 (8)−0.0314 (9)
C210.110 (2)0.0604 (13)0.0830 (15)−0.0210 (13)0.0127 (13)−0.0261 (11)
C220.163 (3)0.099 (2)0.0858 (18)−0.027 (2)0.0238 (19)−0.0308 (16)

Geometric parameters (Å, °)

S1—C121.7247 (16)C13—C141.424 (3)
S1—C151.728 (2)C14—C151.362 (2)
O1—C31.331 (2)C14—C161.505 (3)
O2—C171.201 (3)C15—C201.466 (3)
O3—C171.332 (3)C18—C191.448 (5)
O3—C181.449 (2)C21—C221.447 (4)
O4—C201.195 (3)C1—H10.9300
O5—C201.335 (2)C4—H40.9300
O5—C211.445 (3)C5—H50.9300
O1—H1A0.8200C7—H70.9300
N1—C121.379 (2)C8—H80.9300
N1—C11.291 (2)C9—H90.9300
C1—C21.429 (2)C10—H100.9300
C2—C31.396 (2)C16—H16A0.9600
C2—C111.445 (2)C16—H16B0.9600
C3—C41.413 (3)C16—H16C0.9600
C4—C51.350 (3)C18—H18A0.9700
C5—C61.414 (3)C18—H18B0.9700
C6—C111.416 (3)C19—H19A0.9600
C6—C71.412 (3)C19—H19B0.9600
C7—C81.357 (3)C19—H19C0.9600
C8—C91.389 (3)C21—H21A0.9700
C9—C101.367 (3)C21—H21B0.9700
C10—C111.412 (2)C22—H22A0.9600
C12—C131.383 (2)C22—H22B0.9600
C13—C171.478 (2)C22—H22C0.9600
S1···O52.7985 (16)C14···C11i3.487 (2)
S1···C2i3.6620 (17)C15···C2i3.592 (3)
S1···C3i3.6260 (18)C15···C3i3.581 (3)
S1···H12.5900C16···O22.993 (3)
O1···O33.209 (2)C16···O42.978 (3)
O1···N12.561 (2)C20···C4i3.523 (3)
O2···C162.993 (3)C1···H102.6600
O3···N12.8195 (18)C1···H1A2.3900
O3···O13.209 (2)C8···H18Bviii3.0700
O4···C162.978 (3)C8···H16Ai3.1000
O4···C7ii3.269 (3)C9···H16Ai3.0700
O5···S12.7985 (16)C10···H12.6400
O1···H19C2.6600C12···H1A3.0200
O2···H18A2.5600C17···H16A2.9200
O2···H21Biii2.6000C20···H16C2.7100
O2···H9iv2.6100C20···H16Biii2.9700
O2···H16A2.8300H1···S12.5900
O2···H18Av2.7200H1···C102.6400
O2···H16B2.7300H1···H102.0800
O2···H18B2.6900H1A···O32.5800
O3···H1A2.5800H1A···N11.8300
O3···H10i2.9100H1A···C12.3900
O4···H7ii2.3700H1A···C123.0200
O4···H21A2.5100H5···H72.4600
O4···H21B2.7400H7···O4vii2.3700
O4···H16C2.2500H7···H52.4600
O5···H16Biii2.9100H9···O2viii2.6100
N1···O12.561 (2)H10···C12.6600
N1···O32.8195 (18)H10···H12.0800
N1···C6vi3.369 (2)H10···O3i2.9100
N1···H1A1.8300H16A···O22.8300
C1···C6vi3.531 (3)H16A···C172.9200
C1···C12i3.319 (2)H16A···C8i3.1000
C1···C5vi3.469 (3)H16A···C9i3.0700
C2···C11vi3.594 (2)H16B···O22.7300
C2···C15i3.592 (3)H16B···O5iii2.9100
C2···S1i3.6620 (17)H16B···C20iii2.9700
C2···C2vi3.469 (2)H16C···O42.2500
C3···C11vi3.519 (3)H16C···C202.7100
C3···C15i3.581 (3)H18A···O22.5600
C3···S1i3.6260 (18)H18A···O2v2.7200
C4···C20i3.523 (3)H18B···O22.6900
C5···C1vi3.469 (3)H18B···C8iv3.0700
C6···N1vi3.369 (2)H19B···H22Bix2.6000
C6···C1vi3.531 (3)H19C···O12.6600
C7···O4vii3.269 (3)H21A···O42.5100
C11···C3vi3.519 (3)H21B···O42.7400
C11···C14i3.487 (2)H21B···O2iii2.6000
C11···C2vi3.594 (2)H22B···H19Bx2.6000
C12···C1i3.319 (2)
C12—S1—C1590.91 (9)O5—C21—C22108.0 (2)
C17—O3—C18116.55 (16)N1—C1—H1119.00
C20—O5—C21116.42 (17)C2—C1—H1119.00
C3—O1—H1A109.00C3—C4—H4120.00
C1—N1—C12121.62 (14)C5—C4—H4120.00
N1—C1—C2122.21 (14)C4—C5—H5119.00
C1—C2—C11120.78 (14)C6—C5—H5119.00
C3—C2—C11119.38 (16)C6—C7—H7119.00
C1—C2—C3119.82 (15)C8—C7—H7119.00
O1—C3—C2123.00 (17)C7—C8—H8120.00
C2—C3—C4120.20 (16)C9—C8—H8120.00
O1—C3—C4116.80 (15)C8—C9—H9120.00
C3—C4—C5120.63 (17)C10—C9—H9120.00
C4—C5—C6121.71 (19)C9—C10—H10119.00
C5—C6—C11119.22 (16)C11—C10—H10119.00
C7—C6—C11119.68 (16)C14—C16—H16A109.00
C5—C6—C7121.10 (18)C14—C16—H16B109.00
C6—C7—C8121.1 (2)C14—C16—H16C110.00
C7—C8—C9119.68 (19)H16A—C16—H16B109.00
C8—C9—C10120.87 (17)H16A—C16—H16C110.00
C9—C10—C11121.34 (18)H16B—C16—H16C109.00
C2—C11—C6118.85 (14)O3—C18—H18A110.00
C6—C11—C10117.30 (15)O3—C18—H18B110.00
C2—C11—C10123.85 (16)C19—C18—H18A110.00
S1—C12—N1123.46 (12)C19—C18—H18B110.00
S1—C12—C13111.39 (13)H18A—C18—H18B108.00
N1—C12—C13125.11 (14)C18—C19—H19A109.00
C12—C13—C14113.15 (14)C18—C19—H19B109.00
C12—C13—C17123.98 (17)C18—C19—H19C109.00
C14—C13—C17122.84 (16)H19A—C19—H19B110.00
C13—C14—C16123.87 (16)H19A—C19—H19C109.00
C15—C14—C16124.86 (18)H19B—C19—H19C109.00
C13—C14—C15111.23 (16)O5—C21—H21A110.00
S1—C15—C14113.31 (15)O5—C21—H21B110.00
C14—C15—C20127.68 (18)C22—C21—H21A110.00
S1—C15—C20118.98 (14)C22—C21—H21B110.00
O2—C17—O3123.34 (17)H21A—C21—H21B108.00
O3—C17—C13112.87 (16)C21—C22—H22A109.00
O2—C17—C13123.8 (2)C21—C22—H22B109.00
O3—C18—C19109.3 (2)C21—C22—H22C109.00
O4—C20—O5123.28 (19)H22A—C22—H22B109.00
O5—C20—C15111.10 (18)H22A—C22—H22C109.00
O4—C20—C15125.61 (19)H22B—C22—H22C109.00
C15—S1—C12—C130.71 (14)C5—C6—C11—C10178.60 (17)
C12—S1—C15—C14−1.17 (15)C5—C6—C7—C8−179.4 (2)
C12—S1—C15—C20176.74 (16)C7—C6—C11—C2178.44 (17)
C15—S1—C12—N1178.59 (15)C11—C6—C7—C81.0 (3)
C18—O3—C17—O20.1 (3)C6—C7—C8—C90.7 (3)
C17—O3—C18—C19−174.4 (3)C7—C8—C9—C10−1.5 (3)
C18—O3—C17—C13179.2 (2)C8—C9—C10—C110.6 (3)
C21—O5—C20—C15−177.41 (18)C9—C10—C11—C61.0 (3)
C20—O5—C21—C22169.1 (2)C9—C10—C11—C2−179.21 (18)
C21—O5—C20—O42.0 (3)S1—C12—C13—C14−0.1 (2)
C12—N1—C1—C2−177.45 (16)N1—C12—C13—C170.3 (3)
C1—N1—C12—C13178.89 (17)N1—C12—C13—C14−177.96 (16)
C1—N1—C12—S11.3 (2)S1—C12—C13—C17178.14 (15)
N1—C1—C2—C11177.84 (16)C17—C13—C14—C15−179.04 (17)
N1—C1—C2—C3−0.6 (3)C12—C13—C14—C16−178.26 (17)
C1—C2—C3—C4178.30 (17)C12—C13—C14—C15−0.7 (2)
C11—C2—C3—C4−0.2 (3)C17—C13—C14—C163.4 (3)
C1—C2—C3—O1−1.7 (3)C14—C13—C17—O3−143.40 (18)
C11—C2—C3—O1179.81 (17)C12—C13—C17—O2−142.4 (2)
C1—C2—C11—C6−177.67 (16)C14—C13—C17—O235.7 (3)
C1—C2—C11—C102.6 (3)C12—C13—C17—O338.5 (2)
C3—C2—C11—C10−178.99 (17)C13—C14—C15—C20−176.40 (18)
C3—C2—C11—C60.8 (2)C16—C14—C15—S1178.78 (15)
O1—C3—C4—C5180.00 (19)C16—C14—C15—C201.1 (3)
C2—C3—C4—C50.0 (3)C13—C14—C15—S11.3 (2)
C3—C4—C5—C6−0.4 (3)C14—C15—C20—O5173.23 (19)
C4—C5—C6—C111.0 (3)S1—C15—C20—O4176.31 (18)
C4—C5—C6—C7−178.60 (19)S1—C15—C20—O5−4.4 (2)
C5—C6—C11—C2−1.2 (3)C14—C15—C20—O4−6.1 (3)
C7—C6—C11—C10−1.8 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y+1, z; (iii) −x+1, −y+2, −z+1; (iv) x, y, z+1; (v) −x+1, −y+1, −z+2; (vi) −x, −y+1, −z+1; (vii) x−1, y−1, z; (viii) x, y, z−1; (ix) x, y−1, z+1; (x) x, y+1, z−1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···O30.822.583.209 (2)135
O1—H1A···N10.821.832.561 (2)147
C1—H1···S10.932.593.0263 (18)109
C7—H7···O4vii0.932.373.269 (3)163
C16—H16C···O40.962.252.978 (3)132
C21—H21B···O2iii0.972.603.565 (3)175

Symmetry codes: (vii) x−1, y−1, z; (iii) −x+1, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2483).

References

  • Akkurt, M., Karaca, S., Asiri, A. M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o869. [PMC free article] [PubMed]
  • Akkurt, M., Yıldırım, S. Ö., Asiri, A. M. & McKee, V. (2008). Acta Cryst. E64, o682. [PMC free article] [PubMed]
  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Asiri, A. M. & Badahdah, K. O. (2007). Molecules, 12, 1796-1804. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stoe & Cie (2002). X-AREA and X-RED32 Stoe & Cie, Darmstadt, Germany.

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