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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3172
https://doi.org/10.1107/S1600536810045496

(2Z)-4-[(2-Hy­dr­oxy­phen­yl)carbamo­yl]prop-2-enoic acid

Farooq Ali Shah,a Saqib Ali,a M. Nawaz Tahirb* and Sajjad Ahmeda

aDepartment of Chemistry, Quaid-e-Azam University, Islamabad, Pakistan, and bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 1 November 2010; accepted 5 November 2010; online 13 November 2010)

In the title compound, C10H9NO4, the 2-hy­droxy­anilinic and the 4-oxobut-2-enoic acid groups are almost planar, with r.m.s. deviations of 0.0086 and 0.0262 Å, respectively. The dihedral angle between the two groups is 6.65 (1)°. Intra­molecular N—H⋯O, C—H⋯O and O—H⋯O hydrogen bonds form S(5), S(6) and S(7) ring motifs. In the crystal, the mol­ecules are dimerized due to C—H⋯O and O—H⋯O inter­molecular hydrogen bonds, with R22(8) ring motifs. The dimers are inter­linked into polymeric chains along [010] with R43(13) ring motifs by C—H⋯O, N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For background and a related structure, see: Shah et al. (2008[Shah, F. A., Tahir, M. N. & Ali, S. (2008). Acta Cryst. E64, o1661.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C10H9NO4

  • Mr = 207.18

  • Orthorhombic, P 21 21 21

  • a = 6.7873 (3) Å

  • b = 10.6855 (4) Å

  • c = 12.8442 (4) Å

  • V = 931.54 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 296 K

  • 0.32 × 0.25 × 0.24 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.978

  • 4118 measured reflections

  • 997 independent reflections

  • 944 reflections with I > 2σ(I)

  • Rint = 0.015
Refinement

  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.082

  • S = 1.09

  • 997 reflections

  • 138 parameters

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1 0.86 2.20 2.6111 (19) 109
O1—H1A⋯O4i 0.82 1.94 2.7282 (18) 162
O3—H3A⋯O2 0.82 1.67 2.4881 (18) 175
C3—H3⋯O3i 0.93 2.47 3.374 (2) 164
C6—H6⋯O2 0.93 2.26 2.850 (2) 121
C8—H8⋯O4ii 0.93 2.57 3.404 (2) 150
Symmetry codes: (i) x, y-1, z; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045496/bq2250sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045496/bq2250Isup2.hkl

checkCIF report


Comment top

We reported the crystal structure of (II) i.e., 4-[(2-Fluorophenyl)amino]-4-oxobutanoic acid (Shah et al., 2008), previously. The title compound (I, Fig. 1), has been prepared in continuation to synthesize substituted oxobutanoic acids.

In (I), the 2-hydroxyanilinic group (C1—C6/O1/N1) and the other part i.e., 4-oxobut-2-enoic acid (C7—C10/O2/O3/O4) are planar with r.m.s. deviation of 0.0086 Å and 0.0262 Å, respectively. The dihedral angle between two groups is 6.65 (1)°. The intramolecular H-bondings of N—H···O, C—H···O and O—H···O types (Table 1, Fig. 1) complete S(5), S(6) and S(7) ring motifs (Bernstein et al., 1995). Generally, the carboxylic acids are dimerized through O—H···O bonds with R22(8) ring motifs but the molecules of (I) are dimerized in a different way. The molecules of (I) are dimerized due to C—H···O and O—H···O intermolecular H-bondings with R22(8) ring motifs (Table 1, Fig. 2). In these dimers the donor and accepter groups are from separate molecules. This change has been occurred due to the attachment of hydroxy group at the position-2 of benzene ring and the presence of carbonyl group. The dimers are interlinked in the form of polymeric chains extending along the crystallographic b-axis i.e., along [010] with R43(13) ring motifs due to C—H···O, N—H···O and O—H···O tyeps of H-bondings (Table 1, Fig. 2).

Related literature top

For related background and a related structure, see: Shah et al. (2008). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

2-Hydroxyaniline (10.9 g, 0.1 mol) was dissolved in 30 ml of glacial acetic acid. A solution of Maleic anhydride (9.8 g, 0.1 mol) in 50 ml glacial acetic acid was added and the mixture was stirred overnight. The precipitate which appeared were filtered, washed with distilled water and dried at 313–315 K. The acid was recrystallized from acetone to get yellow prisms of title compound. (Yield: 85%, m.p. 415 K)

Refinement top

The H-atoms were positioned geometrically with (O—H = 0.82, N—H = 0.86, C–H = 0.93 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = xUeq(C, N, O), where x = 1.2 for all H-atoms.

Structure description top

We reported the crystal structure of (II) i.e., 4-[(2-Fluorophenyl)amino]-4-oxobutanoic acid (Shah et al., 2008), previously. The title compound (I, Fig. 1), has been prepared in continuation to synthesize substituted oxobutanoic acids.

In (I), the 2-hydroxyanilinic group (C1—C6/O1/N1) and the other part i.e., 4-oxobut-2-enoic acid (C7—C10/O2/O3/O4) are planar with r.m.s. deviation of 0.0086 Å and 0.0262 Å, respectively. The dihedral angle between two groups is 6.65 (1)°. The intramolecular H-bondings of N—H···O, C—H···O and O—H···O types (Table 1, Fig. 1) complete S(5), S(6) and S(7) ring motifs (Bernstein et al., 1995). Generally, the carboxylic acids are dimerized through O—H···O bonds with R22(8) ring motifs but the molecules of (I) are dimerized in a different way. The molecules of (I) are dimerized due to C—H···O and O—H···O intermolecular H-bondings with R22(8) ring motifs (Table 1, Fig. 2). In these dimers the donor and accepter groups are from separate molecules. This change has been occurred due to the attachment of hydroxy group at the position-2 of benzene ring and the presence of carbonyl group. The dimers are interlinked in the form of polymeric chains extending along the crystallographic b-axis i.e., along [010] with R43(13) ring motifs due to C—H···O, N—H···O and O—H···O tyeps of H-bondings (Table 1, Fig. 2).

For related background and a related structure, see: Shah et al. (2008). For graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title compound with the atom numbering scheme. The thermal displacements are drawn at the 50% probability level. The dotted line indicate the intramolecular H-bond.
[Figure 2] Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form one-dimensional polymeric network due to strong intermolecular H-bondings.
(2Z)-4-[(2-Hydroxyphenyl)carbamoyl]prop-2-enoic acid top
Crystal data top
C10H9NO4F(000) = 432
Mr = 207.18Dx = 1.477 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 944 reflections
a = 6.7873 (3) Åθ = 3.2–25.2°
b = 10.6855 (4) ŵ = 0.12 mm−1
c = 12.8442 (4) ÅT = 296 K
V = 931.54 (6) Å3Prism, yellow
Z = 40.32 × 0.25 × 0.24 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		997 independent reflections
Radiation source: fine-focus sealed tube944 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
Detector resolution: 8.2 pixels mm-1θmax = 25.2°, θmin = 3.2°
ω scansh = −7→8
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −12→12
Tmin = 0.968, Tmax = 0.978l = −15→14
4118 measured reflections
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.050P)2 + 0.1393P]
where P = (Fo2 + 2Fc2)/3
997 reflections(Δ/σ)max < 0.001
138 parametersΔρmax = 0.17 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C10H9NO4V = 931.54 (6) Å3
Mr = 207.18Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.7873 (3) ŵ = 0.12 mm−1
b = 10.6855 (4) ÅT = 296 K
c = 12.8442 (4) Å0.32 × 0.25 × 0.24 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		997 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		944 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.978Rint = 0.015
4118 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.082H-atom parameters constrained
S = 1.09Δρmax = 0.17 e Å−3
997 reflectionsΔρmin = −0.18 e Å−3
138 parameters
Special details top

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 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
O10.0644 (3)−0.02680 (12)0.57792 (9)0.0460 (5)
O20.0945 (3)0.39908 (12)0.45571 (10)0.0498 (5)
O30.0839 (4)0.62508 (12)0.50201 (11)0.0565 (6)
O40.0659 (3)0.73178 (12)0.64703 (12)0.0519 (5)
N10.0940 (3)0.21180 (13)0.53692 (11)0.0339 (4)
C10.0933 (3)0.12928 (16)0.45057 (14)0.0311 (5)
C20.0788 (3)0.00188 (16)0.47494 (13)0.0333 (5)
C30.0808 (3)−0.08600 (17)0.39600 (15)0.0397 (6)
C40.0939 (4)−0.04766 (19)0.29330 (16)0.0416 (6)
C50.1054 (3)0.07754 (19)0.26907 (14)0.0403 (6)
C60.1071 (3)0.16658 (18)0.34720 (14)0.0358 (5)
C70.0946 (3)0.33779 (16)0.53732 (14)0.0312 (5)
C80.0967 (3)0.39436 (16)0.64192 (14)0.0341 (5)
C90.0918 (3)0.51549 (17)0.66740 (14)0.0366 (5)
C100.0796 (3)0.63080 (16)0.60326 (15)0.0384 (6)
H10.093950.176690.597170.0407*
H1A0.06683−0.103020.585220.0552*
H30.07345−0.170790.411870.0476*
H3A0.092100.551760.483670.0677*
H40.09499−0.106950.240300.0499*
H50.111940.102430.199780.0483*
H60.117530.251040.330630.0430*
H80.102150.338500.697360.0409*
H90.097000.530390.738680.0439*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0805 (11)0.0226 (6)0.0350 (7)0.0016 (8)−0.0057 (7)0.0025 (5)
O20.0934 (12)0.0237 (6)0.0322 (7)0.0007 (8)−0.0019 (10)0.0017 (5)
O30.1077 (14)0.0221 (7)0.0396 (8)0.0033 (10)−0.0012 (10)0.0015 (5)
O40.0801 (11)0.0239 (6)0.0518 (9)−0.0005 (8)−0.0008 (9)−0.0067 (6)
N10.0494 (9)0.0225 (7)0.0299 (7)0.0008 (8)−0.0004 (9)0.0006 (5)
C10.0335 (9)0.0249 (9)0.0350 (9)0.0011 (8)−0.0023 (10)−0.0039 (7)
C20.0402 (9)0.0262 (9)0.0335 (9)0.0014 (9)−0.0038 (9)0.0005 (7)
C30.0480 (11)0.0256 (9)0.0455 (11)−0.0017 (10)−0.0046 (11)−0.0065 (8)
C40.0467 (12)0.0376 (10)0.0404 (10)−0.0027 (10)−0.0003 (10)−0.0120 (8)
C50.0449 (12)0.0440 (11)0.0319 (9)−0.0015 (11)−0.0008 (10)−0.0026 (8)
C60.0426 (10)0.0302 (9)0.0347 (9)0.0011 (9)0.0009 (10)0.0018 (8)
C70.0374 (9)0.0213 (8)0.0348 (9)0.0002 (8)−0.0006 (10)0.0014 (7)
C80.0446 (11)0.0257 (8)0.0319 (9)−0.0006 (10)0.0016 (10)0.0040 (7)
C90.0466 (10)0.0314 (9)0.0318 (9)−0.0016 (10)0.0028 (10)−0.0031 (7)
C100.0481 (12)0.0245 (9)0.0427 (10)−0.0014 (10)−0.0009 (11)−0.0025 (8)
Geometric parameters (Å, º) top
O1—C21.361 (2)C3—C41.384 (3)
O2—C71.236 (2)C4—C51.376 (3)
O3—C101.302 (2)C5—C61.383 (3)
O4—C101.220 (2)C7—C81.473 (3)
O1—H1A0.8200C8—C91.336 (2)
O3—H3A0.8200C9—C101.485 (3)
N1—C11.417 (2)C3—H30.9300
N1—C71.346 (2)C4—H40.9300
N1—H10.8600C5—H50.9300
C1—C21.400 (2)C6—H60.9300
C1—C61.389 (3)C8—H80.9300
C2—C31.382 (3)C9—H90.9300
O1···O4i2.7282 (18)C7···C1viii3.424 (3)
O1···N12.6111 (19)C8···C6ix3.528 (3)
O1···C5ii3.368 (3)C8···C1ix3.583 (3)
O2···C103.120 (2)C8···C6viii3.389 (3)
O2···C62.850 (2)C8···C5viii3.538 (3)
O2···O32.4881 (18)C8···O4vi3.404 (2)
O3···O22.4881 (18)C9···C5viii3.543 (3)
O3···C3iii3.374 (2)C9···C4viii3.434 (3)
O3···C73.104 (2)C9···C4ix3.462 (3)
O4···C8iv3.404 (2)C9···C3ix3.500 (3)
O4···C5v3.404 (3)C10···C3viii3.419 (3)
O4···O1iii2.7282 (18)C10···O23.120 (2)
O1···H12.2000C10···C3ix3.435 (3)
O1···H5ii2.8200C4···H6xii3.0400
O1···H9vi2.6700C6···H4vii3.0000
O2···H62.2600C7···H3A2.3900
O2···H4vii2.8300C7···H62.8200
O2···H3A1.6700C8···H3A2.6400
O3···H3iii2.4700C10···H1Aiii2.8600
O4···H5v2.8900H1···O12.2000
O4···H1Aiii1.9400H1···H82.1600
O4···H8iv2.5700H1A···O4i1.9400
N1···O12.6111 (19)H1A···C10i2.8600
C1···C7viii3.407 (3)H1A···H32.3400
C1···C7ix3.424 (3)H3···O3i2.4700
C1···C8viii3.583 (3)H3···H1A2.3400
C3···O3i3.374 (2)H3A···O21.6700
C3···C9viii3.500 (3)H3A···C72.3900
C3···C10viii3.435 (3)H3A···C82.6400
C3···C10ix3.419 (3)H4···O2xii2.8300
C4···C9viii3.462 (3)H4···C6xii3.0000
C4···C9ix3.434 (3)H4···H6xii2.2800
C5···C8ix3.538 (3)H5···O1x2.8200
C5···O1x3.368 (3)H5···O4xi2.8900
C5···O4xi3.404 (3)H6···O22.2600
C5···C9ix3.543 (3)H6···C72.8200
C6···C8ix3.389 (3)H6···C4vii3.0400
C6···O22.850 (2)H6···H4vii2.2800
C6···C8viii3.528 (3)H8···H12.1600
C7···C1ix3.407 (3)H8···O4vi2.5700
C7···O33.104 (2)H9···O1iv2.6700
C2—O1—H1A109.00C7—C8—C9128.38 (17)
C10—O3—H3A109.00C8—C9—C10132.05 (17)
C1—N1—C7128.71 (15)O3—C10—C9120.93 (15)
C1—N1—H1116.00O4—C10—C9118.85 (17)
C7—N1—H1116.00O3—C10—O4120.22 (17)
N1—C1—C6124.70 (16)C2—C3—H3120.00
C2—C1—C6119.82 (16)C4—C3—H3120.00
N1—C1—C2115.48 (15)C3—C4—H4120.00
C1—C2—C3119.73 (16)C5—C4—H4120.00
O1—C2—C1116.18 (15)C4—C5—H5120.00
O1—C2—C3124.10 (16)C6—C5—H5120.00
C2—C3—C4119.91 (17)C1—C6—H6120.00
C3—C4—C5120.47 (18)C5—C6—H6120.00
C4—C5—C6120.35 (17)C7—C8—H8116.00
C1—C6—C5119.70 (17)C9—C8—H8116.00
O2—C7—N1121.78 (16)C8—C9—H9114.00
O2—C7—C8123.78 (16)C10—C9—H9114.00
N1—C7—C8114.44 (15)
C7—N1—C1—C2−175.7 (2)O1—C2—C3—C4179.3 (2)
C7—N1—C1—C64.8 (4)C1—C2—C3—C4−1.0 (3)
C1—N1—C7—O20.0 (4)C2—C3—C4—C50.1 (4)
C1—N1—C7—C8−179.6 (2)C3—C4—C5—C61.0 (4)
N1—C1—C2—O10.9 (3)C4—C5—C6—C1−1.2 (3)
N1—C1—C2—C3−178.76 (19)O2—C7—C8—C92.6 (4)
C6—C1—C2—O1−179.54 (19)N1—C7—C8—C9−177.8 (2)
C6—C1—C2—C30.8 (3)C7—C8—C9—C101.2 (4)
N1—C1—C6—C5179.9 (2)C8—C9—C10—O3−4.4 (4)
C2—C1—C6—C50.3 (3)C8—C9—C10—O4175.8 (2)
Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, −y, z+1/2; (iii) x, y+1, z; (iv) −x, y+1/2, −z+3/2; (v) −x+1/2, −y+1, z+1/2; (vi) −x, y−1/2, −z+3/2; (vii) −x, y+1/2, −z+1/2; (viii) x−1/2, −y+1/2, −z+1; (ix) x+1/2, −y+1/2, −z+1; (x) −x+1/2, −y, z−1/2; (xi) −x+1/2, −y+1, z−1/2; (xii) −x, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.202.6111 (19)109
O1—H1A···O4i0.821.942.7282 (18)162
O3—H3A···O20.821.672.4881 (18)175
C3—H3···O3i0.932.473.374 (2)164
C6—H6···O20.932.262.850 (2)121
C8—H8···O4vi0.932.573.404 (2)150
Symmetry codes: (i) x, y−1, z; (vi) −x, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC10H9NO4
Mr207.18
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)6.7873 (3), 10.6855 (4), 12.8442 (4)
V (Å3)931.54 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.12
Crystal size (mm)0.32 × 0.25 × 0.24
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.968, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections		4118, 997, 944
Rint0.015
(sin θ/λ)max (Å−1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.082, 1.09
No. of reflections997
No. of parameters138
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.17, −0.18

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.202.6111 (19)109
O1—H1A···O4i0.821.942.7282 (18)162
O3—H3A···O20.821.672.4881 (18)175
C3—H3···O3i0.932.473.374 (2)164
C6—H6···O20.932.262.850 (2)121
C8—H8···O4ii0.932.573.404 (2)150
Symmetry codes: (i) x, y−1, z; (ii) −x, y−1/2, −z+3/2.
 

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
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 First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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 First citationShah, F. A., Tahir, M. N. & Ali, S. (2008). Acta Cryst. E64, o1661.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals 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.

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3172
https://doi.org/10.1107/S1600536810045496
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