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ISSN: 2056-9890

Methyl 2-[(2-chloro­quinolin-3-yl)(hy­dr­oxy)meth­yl]acrylate

aPost Graduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: seshadri_pr@yahoo.com

(Received 22 April 2013; accepted 21 May 2013; online 31 May 2013)

There are two independent mol­ecules (A and B) in the asymmetric unit of the title compound, C14H12ClNO3. The mean planes of the methyl ester unit (Cmeth­yl—O—C=O; r.m.s. deviation = 0.051 Å for mol­ecule A and 0.016 Å for mol­ecule B) and the chloro­quilonine ring system (r.m.s. deviation = 0.023 Å for mol­ecule A and 0.014 Å for mol­ecule B) form dihedral angles of 63.5 (1)° in mol­ecule A and 78.1 (1)° in mol­ecule B. The main difference between the two independent mol­ecules is reflected in the (H)O—C—C=C(H2) torsion angle which is −109.7 (2)° in mol­ecule A and 10.6 (2)° in mol­ecule B. An intra­molecular O—H⋯O hydrogen bond is observed in mol­ecule A. In the crystal, mol­ecules A and B are linked into pairs via bifurcated O—H⋯(N,Cl) hydrogen bonds and a weak C—H⋯O hydrogen bond links pairs of mol­ecules into chains along [100].

Related literature

For the biological activity of quilonine compounds, see: Biavatti et al. (2002[Biavatti, M. W., Vieira, P. C., da Silva, M. F. G. F., Fernandes, J. B., Victor, S. R., Pagnocca, F. C., Albuquerque, S., Caracelli, I. & Zukerman-Schpector, J. (2002). J. Braz. Chem. Soc. 13, 66-70.]); Towers et al. (1981[Towers, G. H. N., Graham, E. A., Spenser, I. D. & Abramowski, Z. (1981). Planta Med. 41, 136-142.]); Shen et al. (1999[Shen, A. Y., Wu, S. N. & Chiu, C. T. (1999). J. Pharm. Pharmacol. 51, 543-548.]). For their luminescent properties, see: Montes et al. (2006[Montes, V. A., Pohl, R., Shinar, J. & Anzenbacher, P. Jr (2006). Chem. Eur. J. 12, 4523-4535.]). For applications of acrylate compounds, see: Bhatia et al. (2007[Bhatia, S. P., Wellington, G. A., Cocchiara, J., Lalko, J., Letizia, C. S. & Api, A. M. (2007). J. Food Chem. Toxicol. 45, S113-S119.]); Sharma (2011[Sharma, P. (2011). J. Chem. Pharm. Res. 3, 403-423.]). For conformational aspects of methyl esters, see: Dunitz & Schweizer (1982[Dunitz, J. D. & Schweizer, B. W. (1982). Helv. Chim. Acta, 65, 1547-1554.]). For resonance effects in acrylates, see: Merlino (1971[Merlino, S. (1971). Acta Cryst. B27, 2491-2492.]); Varghese et al. (1986[Varghese, B., Srinivasan, S., Padmanabhan, P. V. & Ramadas, S. R. (1986). Acta Cryst. C42, 1544-1546.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO3

  • Mr = 277.70

  • Triclinic, [P \overline 1]

  • a = 9.2614 (4) Å

  • b = 11.0309 (4) Å

  • c = 13.8161 (6) Å

  • α = 102.557 (2)°

  • β = 100.646 (2)°

  • γ = 103.704 (2)°

  • V = 1296.29 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.30 mm−1

  • T = 293 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • 14402 measured reflections

  • 4466 independent reflections

  • 3767 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.093

  • S = 1.03

  • 4466 reflections

  • 344 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1A—H1A⋯O2A 0.82 2.24 2.8372 (19) 130
O1B—H1B⋯Cl1Ai 0.82 2.79 3.5040 (12) 147
O1B—H1B⋯N1Ai 0.82 2.16 2.8609 (17) 144
C5A—H5A⋯O1Bii 0.93 2.56 3.451 (2) 162
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The quinoline ring is found in compounds with antifungal (Biavatti et al., 2002), antibacterial (Towers et al., 1981) and anticancer (Shen et al., 1999) properties. Quinoline derivatives have been used for their luminescent properties as organic light-emitting diode (OLED) materials (Montes et al., 2006). Methyl acrylate is an ingredient used in many fragrances and decorative cosmetics (Bhatia et al., 2007; Sharma, 2011). In view of the potential importance of the title compound its crystal structure is presented herein.

The asymmetric unit of the title compound contains the two independent molecules, A and B (Fig. 1). The dihedral angle between the mean plane of methyl ester unit (C13/C14/O2/O3, r.m.s deviation = -0.051 Å for A and -0.016 Å for B) and the chloroquilonin ring system (C1—C9/N1/Cl1, r.m.s deviation = 0.023 Å for A and -0.014 Å for B) is 63.5 (1)° in molecule A and 78.6 (1)° in molecule B. The main difference between the two independent molecules is reflected in the O1—C10—C11—C12 torsion angle which is -109.7 (2)° in molecule A and 10.6 (2)° in molecule B.

The methyl ester moiety adopts an extended conformation as reflected by the torsion angles for C11—C13—C14—O3 = 177.7 (2)° in A and 178.4 (1)° in B. The extended conformation is supported by the fact that the bond angles involving the carbonyl O atoms are invariably expanded (Dunitz & Schweizer, 1982). The significant difference in the bond lengths of the C13—O3 = 1.322 (3) Å (A) 1.331 (3) Å (B) versus C14—O3 = 1.447 (3) Å (A) and 1.447 (2) Å (B) can be attributed to a partial contribution from the O-–CO+–C resonance structure of the O2—C13—O3—C14 group (Merlino, 1971). This feature, commonly observed in the carboxylic ester group of these substituents in various compounds has been shown to give average values of 1.340 Å and 1.447 Å respectively for these bonds (Varghese et al., 1986).

In the crystal molecule A and B are linked into pairs via bifurcated O—H···(N,Cl) hydrogen bonds (Fig. 2) and a weak C—H···O hydrogen bond links pairs of molecules into chains along [100].

Related literature top

For the biological activity of quilonine compounds, see: Biavatti et al. (2002); Towers et al. (1981); Shen et al. (1999). For their luminescent properties, see: Montes et al. (2006). For applications of acrylate compounds, see: Bhatia et al. (2007); Sharma (2011). For conformational aspects of methyl esters, see: Dunitz & Schweizer (1982). For resonance effects in acrylates, see: Merlino (1971); Varghese et al. (1986).

Experimental top

A mixture of 2-chloroquinoline-3-carbaldehyde (0.1 g, 0.52 mmol), methyl acrylate (0.071 ml, 0.78 mmol), and DABCO (0.017 g, 0.15 mmol), was kept at room temperature for 7 days. After completion of the reaction (indicated by TLC), the reaction mixture was extracted with ethylacetate (3 τimes 15 ml). The combined organic layer subsequently washed with dil.HCl and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure. The crude product was obtained and purified by column chromatography eluting with 8% ethylacetate in hexane afforded the alcohol methyl 2-((2-chloroquinolin-3-yl)(hydroxy)methyl)acrylate as a colourless solid. X-ray quality crystals were obtained by slow evaporation of a solution of the title compound in ethylacetate.

Refinement top

Hydrogen atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93-0.98 Å, O—H = 0.82° and Uiso(H) = 1.5Ueq(C) for methyl and hydroxyl H atoms and 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound showing 30% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.
Methyl 2-[(2-chloroquinolin-3-yl)(hydroxy)methyl]acrylate top
Crystal data top
C14H12ClNO3Z = 4
Mr = 277.70F(000) = 576
Triclinic, P1Dx = 1.423 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2614 (4) ÅCell parameters from 4551 reflections
b = 11.0309 (4) Åθ = 2.0–25.0°
c = 13.8161 (6) ŵ = 0.30 mm1
α = 102.557 (2)°T = 293 K
β = 100.646 (2)°Block, colourless
γ = 103.704 (2)°0.35 × 0.30 × 0.25 mm
V = 1296.29 (9) Å3
Data collection top
Bruker SMART APEXII
diffractometer
3767 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
ω and ϕ scansh = 1110
14402 measured reflectionsk = 1213
4466 independent reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.0462P)2 + 0.4048P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4466 reflectionsΔρmax = 0.29 e Å3
344 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0040 (11)
Crystal data top
C14H12ClNO3γ = 103.704 (2)°
Mr = 277.70V = 1296.29 (9) Å3
Triclinic, P1Z = 4
a = 9.2614 (4) ÅMo Kα radiation
b = 11.0309 (4) ŵ = 0.30 mm1
c = 13.8161 (6) ÅT = 293 K
α = 102.557 (2)°0.35 × 0.30 × 0.25 mm
β = 100.646 (2)°
Data collection top
Bruker SMART APEXII
diffractometer
3767 reflections with I > 2σ(I)
14402 measured reflectionsRint = 0.022
4466 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.093H-atom parameters constrained
S = 1.03Δρmax = 0.29 e Å3
4466 reflectionsΔρmin = 0.25 e Å3
344 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
Cl1A0.14491 (5)0.05724 (5)0.40164 (4)0.05417 (16)
O1A0.36327 (14)0.23933 (11)0.28015 (10)0.0504 (3)
H1A0.30510.31090.24730.076*
O2A0.05490 (17)0.36860 (13)0.16879 (12)0.0655 (4)
O3A0.03759 (16)0.26279 (14)0.06395 (11)0.0626 (4)
N1A0.42615 (15)0.19802 (13)0.45982 (10)0.0356 (3)
C1A0.33952 (18)0.08303 (15)0.40781 (12)0.0338 (4)
C2A0.58039 (18)0.22445 (15)0.46705 (12)0.0342 (4)
C3A0.6764 (2)0.35052 (17)0.51704 (13)0.0443 (4)
H3A0.63520.41530.54450.053*
C4A0.8297 (2)0.37743 (19)0.52515 (15)0.0520 (5)
H4A0.89290.46110.55830.062*
C5A0.8944 (2)0.2818 (2)0.48466 (15)0.0521 (5)
H5A0.99990.30170.49210.062*
C6A0.8037 (2)0.16025 (19)0.43468 (14)0.0456 (4)
H6A0.84740.09730.40730.055*
C7A0.64369 (18)0.12781 (16)0.42366 (12)0.0350 (4)
C8A0.54251 (18)0.00498 (16)0.36909 (12)0.0356 (4)
H8A0.58170.06040.34010.043*
C9A0.38875 (18)0.02014 (15)0.35779 (12)0.0321 (3)
C10A0.27692 (18)0.14936 (15)0.29730 (12)0.0352 (4)
H10A0.20670.17750.33850.042*
C11A0.18355 (18)0.14703 (15)0.19609 (12)0.0368 (4)
C12A0.2087 (2)0.05086 (19)0.15361 (15)0.0547 (5)
H12A0.14960.05960.08890.066*
H12B0.28550.02590.18830.066*
C13A0.0617 (2)0.27074 (17)0.14275 (14)0.0433 (4)
C14A0.1553 (3)0.3815 (2)0.00547 (18)0.0770 (7)
H14A0.22080.36450.04940.116*
H14B0.21510.41340.04930.116*
H14C0.10820.44510.02230.116*
Cl1B0.34205 (5)0.35070 (5)0.27784 (4)0.05394 (16)
N1B0.52758 (16)0.22798 (12)0.21855 (10)0.0386 (3)
O1B0.71157 (13)0.63179 (11)0.42717 (8)0.0422 (3)
H1B0.70630.70330.45600.063*
O2B0.45974 (15)0.56659 (12)0.12824 (10)0.0530 (3)
O3B0.59711 (17)0.75707 (12)0.11953 (9)0.0553 (4)
C1B0.51958 (18)0.34408 (15)0.25490 (12)0.0342 (4)
C2B0.66394 (19)0.21585 (15)0.19986 (12)0.0357 (4)
C3B0.6778 (2)0.09090 (17)0.16220 (14)0.0482 (5)
H3B0.59440.01840.15000.058*
C4B0.8116 (3)0.07581 (18)0.14373 (16)0.0560 (5)
H4B0.81960.00720.11910.067*
C5B0.9382 (3)0.1835 (2)0.16113 (18)0.0607 (6)
H5B1.02970.17170.14830.073*
C6B0.9281 (2)0.30528 (18)0.19672 (16)0.0532 (5)
H6B1.01250.37640.20740.064*
C7B0.79075 (19)0.32456 (15)0.21766 (13)0.0369 (4)
C8B0.77249 (18)0.44774 (15)0.25652 (12)0.0364 (4)
H8B0.85410.52150.26860.044*
C9B0.63788 (17)0.46076 (14)0.27667 (11)0.0316 (3)
C10B0.62325 (18)0.59300 (14)0.32479 (12)0.0328 (4)
H10B0.51550.58440.32500.039*
C11B0.67326 (18)0.68846 (14)0.26558 (12)0.0335 (4)
C12B0.7998 (2)0.78554 (17)0.29927 (15)0.0470 (4)
H12C0.82460.84160.25950.056*
H12D0.86460.79820.36290.056*
C13B0.5651 (2)0.66278 (15)0.16500 (13)0.0375 (4)
C14B0.4924 (3)0.7379 (2)0.02265 (16)0.0765 (7)
H14D0.52410.81040.00410.115*
H14E0.39090.73040.03210.115*
H14F0.49240.65990.02460.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0291 (2)0.0501 (3)0.0697 (3)0.00871 (19)0.0111 (2)0.0073 (2)
O1A0.0485 (7)0.0334 (6)0.0626 (8)0.0161 (6)0.0061 (6)0.0011 (6)
O2A0.0628 (9)0.0374 (8)0.0763 (10)0.0048 (6)0.0039 (8)0.0076 (7)
O3A0.0484 (8)0.0571 (9)0.0545 (8)0.0067 (6)0.0094 (7)0.0015 (7)
N1A0.0342 (7)0.0321 (7)0.0354 (7)0.0073 (6)0.0065 (6)0.0029 (6)
C1A0.0290 (8)0.0363 (9)0.0329 (8)0.0085 (7)0.0059 (7)0.0052 (7)
C2A0.0332 (9)0.0356 (9)0.0300 (8)0.0054 (7)0.0042 (7)0.0093 (7)
C3A0.0472 (11)0.0356 (9)0.0436 (10)0.0040 (8)0.0095 (8)0.0079 (8)
C4A0.0425 (11)0.0462 (11)0.0518 (11)0.0086 (9)0.0031 (9)0.0129 (9)
C5A0.0308 (9)0.0623 (13)0.0565 (12)0.0009 (9)0.0039 (8)0.0225 (10)
C6A0.0335 (9)0.0544 (11)0.0499 (11)0.0135 (8)0.0089 (8)0.0166 (9)
C7A0.0326 (8)0.0394 (9)0.0323 (8)0.0097 (7)0.0046 (7)0.0122 (7)
C8A0.0359 (9)0.0357 (9)0.0355 (9)0.0129 (7)0.0089 (7)0.0075 (7)
C9A0.0322 (8)0.0316 (8)0.0301 (8)0.0085 (7)0.0063 (6)0.0057 (6)
C10A0.0358 (9)0.0288 (8)0.0383 (9)0.0085 (7)0.0101 (7)0.0042 (7)
C11A0.0329 (9)0.0328 (9)0.0377 (9)0.0039 (7)0.0079 (7)0.0024 (7)
C12A0.0561 (12)0.0461 (11)0.0455 (11)0.0004 (9)0.0049 (9)0.0104 (9)
C13A0.0383 (10)0.0398 (10)0.0422 (10)0.0030 (8)0.0108 (8)0.0001 (8)
C14A0.0527 (13)0.0717 (15)0.0651 (14)0.0098 (11)0.0082 (11)0.0158 (12)
Cl1B0.0352 (2)0.0458 (3)0.0787 (4)0.0054 (2)0.0187 (2)0.0156 (2)
N1B0.0413 (8)0.0290 (7)0.0403 (8)0.0030 (6)0.0077 (6)0.0087 (6)
O1B0.0493 (7)0.0388 (7)0.0343 (6)0.0170 (6)0.0034 (5)0.0026 (5)
O2B0.0555 (8)0.0369 (7)0.0473 (7)0.0006 (6)0.0073 (6)0.0035 (6)
O3B0.0787 (10)0.0391 (7)0.0404 (7)0.0100 (7)0.0008 (6)0.0144 (6)
C1B0.0328 (8)0.0326 (9)0.0348 (9)0.0054 (7)0.0058 (7)0.0110 (7)
C2B0.0450 (10)0.0278 (8)0.0326 (8)0.0078 (7)0.0078 (7)0.0093 (7)
C3B0.0625 (12)0.0281 (9)0.0502 (11)0.0083 (8)0.0157 (9)0.0068 (8)
C4B0.0755 (14)0.0349 (10)0.0615 (13)0.0233 (10)0.0231 (11)0.0080 (9)
C5B0.0591 (13)0.0498 (12)0.0796 (15)0.0261 (10)0.0275 (11)0.0107 (11)
C6B0.0438 (11)0.0393 (10)0.0747 (14)0.0113 (8)0.0193 (10)0.0088 (9)
C7B0.0401 (9)0.0314 (8)0.0385 (9)0.0105 (7)0.0092 (7)0.0085 (7)
C8B0.0337 (9)0.0264 (8)0.0430 (9)0.0032 (7)0.0061 (7)0.0065 (7)
C9B0.0330 (8)0.0287 (8)0.0307 (8)0.0065 (7)0.0044 (7)0.0090 (6)
C10B0.0308 (8)0.0291 (8)0.0348 (9)0.0074 (6)0.0047 (7)0.0051 (7)
C11B0.0350 (9)0.0252 (8)0.0367 (9)0.0089 (7)0.0063 (7)0.0033 (7)
C12B0.0444 (10)0.0370 (10)0.0510 (11)0.0017 (8)0.0039 (8)0.0124 (8)
C13B0.0450 (10)0.0274 (8)0.0376 (9)0.0121 (8)0.0072 (8)0.0047 (7)
C14B0.115 (2)0.0619 (14)0.0432 (12)0.0268 (14)0.0072 (12)0.0172 (10)
Geometric parameters (Å, º) top
Cl1A—C1A1.7396 (16)Cl1B—C1B1.7459 (17)
O1A—C10A1.4228 (19)N1B—C1B1.295 (2)
O1A—H1A0.8200N1B—C2B1.366 (2)
O2A—C13A1.202 (2)O1B—C10B1.4130 (18)
O3A—C13A1.322 (2)O1B—H1B0.8200
O3A—C14A1.447 (2)O2B—C13B1.195 (2)
N1A—C1A1.295 (2)O3B—C13B1.331 (2)
N1A—C2A1.369 (2)O3B—C14B1.441 (2)
C1A—C9A1.415 (2)C1B—C9B1.410 (2)
C2A—C3A1.404 (2)C2B—C7B1.406 (2)
C2A—C7A1.410 (2)C2B—C3B1.408 (2)
C3A—C4A1.358 (3)C3B—C4B1.351 (3)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.397 (3)C4B—C5B1.399 (3)
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.353 (3)C5B—C6B1.358 (3)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C7A1.410 (2)C6B—C7B1.409 (2)
C6A—H6A0.9300C6B—H6B0.9300
C7A—C8A1.406 (2)C7B—C8B1.410 (2)
C8A—C9A1.357 (2)C8B—C9B1.359 (2)
C8A—H8A0.9300C8B—H8B0.9300
C9A—C10A1.505 (2)C9B—C10B1.514 (2)
C10A—C11A1.511 (2)C10B—C11B1.509 (2)
C10A—H10A0.9800C10B—H10B0.9800
C11A—C12A1.315 (3)C11B—C12B1.313 (2)
C11A—C13A1.485 (2)C11B—C13B1.481 (2)
C12A—H12A0.9300C12B—H12C0.9300
C12A—H12B0.9300C12B—H12D0.9300
C14A—H14A0.9600C14B—H14D0.9600
C14A—H14B0.9600C14B—H14E0.9600
C14A—H14C0.9600C14B—H14F0.9600
C10A—O1A—H1A109.5C1B—N1B—C2B117.42 (14)
C13A—O3A—C14A116.51 (17)C10B—O1B—H1B109.5
C1A—N1A—C2A117.75 (14)C13B—O3B—C14B115.36 (15)
N1A—C1A—C9A126.31 (15)N1B—C1B—C9B126.51 (15)
N1A—C1A—Cl1A115.01 (12)N1B—C1B—Cl1B114.43 (12)
C9A—C1A—Cl1A118.68 (12)C9B—C1B—Cl1B119.06 (12)
N1A—C2A—C3A119.28 (15)N1B—C2B—C7B121.77 (14)
N1A—C2A—C7A121.07 (14)N1B—C2B—C3B119.00 (15)
C3A—C2A—C7A119.64 (15)C7B—C2B—C3B119.23 (16)
C4A—C3A—C2A119.69 (18)C4B—C3B—C2B120.34 (18)
C4A—C3A—H3A120.2C4B—C3B—H3B119.8
C2A—C3A—H3A120.2C2B—C3B—H3B119.8
C3A—C4A—C5A121.23 (17)C3B—C4B—C5B120.76 (17)
C3A—C4A—H4A119.4C3B—C4B—H4B119.6
C5A—C4A—H4A119.4C5B—C4B—H4B119.6
C6A—C5A—C4A120.03 (17)C6B—C5B—C4B120.30 (19)
C6A—C5A—H5A120.0C6B—C5B—H5B119.9
C4A—C5A—H5A120.0C4B—C5B—H5B119.9
C5A—C6A—C7A120.83 (18)C5B—C6B—C7B120.46 (18)
C5A—C6A—H6A119.6C5B—C6B—H6B119.8
C7A—C6A—H6A119.6C7B—C6B—H6B119.8
C8A—C7A—C6A123.60 (16)C2B—C7B—C8B117.38 (15)
C8A—C7A—C2A117.83 (15)C2B—C7B—C6B118.91 (15)
C6A—C7A—C2A118.54 (15)C8B—C7B—C6B123.71 (16)
C9A—C8A—C7A121.35 (15)C9B—C8B—C7B121.30 (15)
C9A—C8A—H8A119.3C9B—C8B—H8B119.3
C7A—C8A—H8A119.3C7B—C8B—H8B119.3
C8A—C9A—C1A115.59 (14)C8B—C9B—C1B115.61 (14)
C8A—C9A—C10A122.69 (14)C8B—C9B—C10B120.66 (14)
C1A—C9A—C10A121.72 (14)C1B—C9B—C10B123.64 (14)
O1A—C10A—C9A107.26 (13)O1B—C10B—C11B112.74 (13)
O1A—C10A—C11A109.72 (13)O1B—C10B—C9B106.54 (12)
C9A—C10A—C11A113.64 (13)C11B—C10B—C9B111.38 (13)
O1A—C10A—H10A108.7O1B—C10B—H10B108.7
C9A—C10A—H10A108.7C11B—C10B—H10B108.7
C11A—C10A—H10A108.7C9B—C10B—H10B108.7
C12A—C11A—C13A121.29 (16)C12B—C11B—C13B122.74 (16)
C12A—C11A—C10A125.54 (15)C12B—C11B—C10B123.77 (15)
C13A—C11A—C10A113.06 (14)C13B—C11B—C10B113.50 (13)
C11A—C12A—H12A120.0C11B—C12B—H12C120.0
C11A—C12A—H12B120.0C11B—C12B—H12D120.0
H12A—C12A—H12B120.0H12C—C12B—H12D120.0
O2A—C13A—O3A123.47 (17)O2B—C13B—O3B123.36 (15)
O2A—C13A—C11A122.95 (17)O2B—C13B—C11B123.22 (15)
O3A—C13A—C11A113.58 (16)O3B—C13B—C11B113.42 (14)
O3A—C14A—H14A109.5O3B—C14B—H14D109.5
O3A—C14A—H14B109.5O3B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
O3A—C14A—H14C109.5O3B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
C2A—N1A—C1A—C9A0.7 (2)C2B—N1B—C1B—C9B0.6 (2)
C2A—N1A—C1A—Cl1A179.69 (11)C2B—N1B—C1B—Cl1B179.34 (11)
C1A—N1A—C2A—C3A175.82 (15)C1B—N1B—C2B—C7B0.9 (2)
C1A—N1A—C2A—C7A3.1 (2)C1B—N1B—C2B—C3B178.77 (15)
N1A—C2A—C3A—C4A179.57 (16)N1B—C2B—C3B—C4B179.50 (17)
C7A—C2A—C3A—C4A1.5 (2)C7B—C2B—C3B—C4B0.2 (3)
C2A—C3A—C4A—C5A0.0 (3)C2B—C3B—C4B—C5B0.3 (3)
C3A—C4A—C5A—C6A1.2 (3)C3B—C4B—C5B—C6B0.2 (3)
C4A—C5A—C6A—C7A0.7 (3)C4B—C5B—C6B—C7B0.7 (3)
C5A—C6A—C7A—C8A177.30 (17)N1B—C2B—C7B—C8B0.4 (2)
C5A—C6A—C7A—C2A0.8 (3)C3B—C2B—C7B—C8B179.26 (15)
N1A—C2A—C7A—C8A2.6 (2)N1B—C2B—C7B—C6B179.98 (16)
C3A—C2A—C7A—C8A176.31 (15)C3B—C2B—C7B—C6B0.3 (2)
N1A—C2A—C7A—C6A179.18 (15)C5B—C6B—C7B—C2B0.8 (3)
C3A—C2A—C7A—C6A1.9 (2)C5B—C6B—C7B—C8B178.76 (19)
C6A—C7A—C8A—C9A177.76 (16)C2B—C7B—C8B—C9B0.5 (2)
C2A—C7A—C8A—C9A0.4 (2)C6B—C7B—C8B—C9B179.11 (17)
C7A—C8A—C9A—C1A2.5 (2)C7B—C8B—C9B—C1B0.8 (2)
C7A—C8A—C9A—C10A178.19 (15)C7B—C8B—C9B—C10B176.02 (14)
N1A—C1A—C9A—C8A2.1 (2)N1B—C1B—C9B—C8B0.3 (2)
Cl1A—C1A—C9A—C8A177.49 (12)Cl1B—C1B—C9B—C8B179.82 (12)
N1A—C1A—C9A—C10A178.61 (16)N1B—C1B—C9B—C10B176.42 (15)
Cl1A—C1A—C9A—C10A1.8 (2)Cl1B—C1B—C9B—C10B3.5 (2)
C8A—C9A—C10A—O1A14.0 (2)C8B—C9B—C10B—O1B70.40 (18)
C1A—C9A—C10A—O1A165.25 (14)C1B—C9B—C10B—O1B106.14 (16)
C8A—C9A—C10A—C11A107.46 (17)C8B—C9B—C10B—C11B52.92 (19)
C1A—C9A—C10A—C11A73.3 (2)C1B—C9B—C10B—C11B130.54 (15)
O1A—C10A—C11A—C12A109.7 (2)O1B—C10B—C11B—C12B10.6 (2)
C9A—C10A—C11A—C12A10.4 (2)C9B—C10B—C11B—C12B109.15 (18)
O1A—C10A—C11A—C13A66.52 (18)O1B—C10B—C11B—C13B169.19 (12)
C9A—C10A—C11A—C13A173.42 (13)C9B—C10B—C11B—C13B71.10 (17)
C14A—O3A—C13A—O2A2.5 (3)C14B—O3B—C13B—O2B1.8 (3)
C14A—O3A—C13A—C11A177.18 (17)C14B—O3B—C13B—C11B178.39 (16)
C12A—C11A—C13A—O2A164.7 (2)C12B—C11B—C13B—O2B170.78 (18)
C10A—C11A—C13A—O2A11.7 (2)C10B—C11B—C13B—O2B9.5 (2)
C12A—C11A—C13A—O3A15.0 (3)C12B—C11B—C13B—O3B9.0 (2)
C10A—C11A—C13A—O3A168.60 (15)C10B—C11B—C13B—O3B170.72 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O2A0.822.242.8372 (19)130
O1B—H1B···Cl1Ai0.822.793.5040 (12)147
O1B—H1B···N1Ai0.822.162.8609 (17)144
C5A—H5A···O1Bii0.932.563.451 (2)162
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC14H12ClNO3
Mr277.70
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.2614 (4), 11.0309 (4), 13.8161 (6)
α, β, γ (°)102.557 (2), 100.646 (2), 103.704 (2)
V3)1296.29 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.30
Crystal size (mm)0.35 × 0.30 × 0.25
Data collection
DiffractometerBruker SMART APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
14402, 4466, 3767
Rint0.022
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.093, 1.03
No. of reflections4466
No. of parameters344
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.25

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O2A0.822.242.8372 (19)129.8
O1B—H1B···Cl1Ai0.822.793.5040 (12)147.4
O1B—H1B···N1Ai0.822.162.8609 (17)144.0
C5A—H5A···O1Bii0.932.563.451 (2)161.5
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1.
 

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT-Madras, India, for the data collection.

References

First citationBhatia, S. P., Wellington, G. A., Cocchiara, J., Lalko, J., Letizia, C. S. & Api, A. M. (2007). J. Food Chem. Toxicol. 45, S113–S119.  Web of Science CrossRef
First citationBiavatti, M. W., Vieira, P. C., da Silva, M. F. G. F., Fernandes, J. B., Victor, S. R., Pagnocca, F. C., Albuquerque, S., Caracelli, I. & Zukerman-Schpector, J. (2002). J. Braz. Chem. Soc. 13, 66–70.  Web of Science CSD CrossRef CAS
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.
First citationDunitz, J. D. & Schweizer, B. W. (1982). Helv. Chim. Acta, 65, 1547–1554.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationMerlino, S. (1971). Acta Cryst. B27, 2491–2492.  CrossRef CAS IUCr Journals Web of Science
First citationMontes, V. A., Pohl, R., Shinar, J. & Anzenbacher, P. Jr (2006). Chem. Eur. J. 12, 4523–4535.  Web of Science CSD CrossRef PubMed CAS
First citationSharma, P. (2011). J. Chem. Pharm. Res. 3, 403–423.  CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShen, A. Y., Wu, S. N. & Chiu, C. T. (1999). J. Pharm. Pharmacol. 51, 543–548.  Web of Science CrossRef PubMed CAS
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationTowers, G. H. N., Graham, E. A., Spenser, I. D. & Abramowski, Z. (1981). Planta Med. 41, 136–142.  CrossRef CAS PubMed Web of Science
First citationVarghese, B., Srinivasan, S., Padmanabhan, P. V. & Ramadas, S. R. (1986). Acta Cryst. C42, 1544–1546.  CSD CrossRef CAS Web of Science IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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