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ISSN: 2056-9890

N-(3-Chloro-4-methyl­phen­yl)succinamic acid

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 17 February 2012; accepted 20 February 2012; online 24 February 2012)

In the crystal structure of the title compound, C11H12ClNO3, the asymmetric unit contains two independent mol­ecules. The N—H bond in the amide segment is anti to the meta-Cl atom in the benzene ring, in both molecules. The amide and carboxyl C=O bonds are also anti to each other and anti to the H atoms on the adjacent –CH2 groups. Furthermore, the C=O and O—H bonds of the acid group are in syn positions with respect to each other. The dihedral angles between the benzene ring and the amide group are 40.6 (2) and 44.9 (3)° in the two independent molecules. In the crystal, mol­ecules are packed into sheets parallel to the (11-3) plane through O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2000[Gowda, B. T., Paulus, H. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 711-720.]); Chaithanya et al. (2012[Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o785.]). For N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570.]). For N-chloro­aryl­amides, see: Gowda et al. (2003[Gowda, B. T., D'Souza, J. D. & Kumar, B. H. A. (2003). Z. Naturforsch. Teil A, 58, 51-56.]); Jyothi & Gowda (2004[Jyothi, K. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 64-68.]). For N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006[Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351-359.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12ClNO3

  • Mr = 241.67

  • Triclinic, [P \overline 1]

  • a = 6.8788 (9) Å

  • b = 7.9713 (9) Å

  • c = 21.119 (3) Å

  • α = 86.76 (1)°

  • β = 86.48 (1)°

  • γ = 79.45 (1)°

  • V = 1135.1 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.33 mm−1

  • T = 293 K

  • 0.42 × 0.14 × 0.08 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.875, Tmax = 0.974

  • 6890 measured reflections

  • 4066 independent reflections

  • 2649 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.083

  • wR(F2) = 0.159

  • S = 1.26

  • 4066 reflections

  • 303 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O4i 0.85 (2) 2.05 (2) 2.882 (5) 165 (5)
O3—H3O⋯O2ii 0.83 (2) 1.83 (2) 2.654 (5) 173 (7)
N2—H2N⋯O1iii 0.84 (2) 2.07 (2) 2.891 (5) 165 (5)
O6—H6O⋯O5iv 0.83 (2) 1.90 (3) 2.703 (5) 164 (7)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y, -z; (iii) -x+1, -y+2, -z+1; (iv) -x+2, -y+3, -z+2.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); data reduction: CrysAlis RED; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000; Chaithanya et al., 2012), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-chloroarylsulfonamides (Gowda et al., 2003; Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(3-Chloro-4-methylphenyl)succinamic acid has been determined (Fig. 1). The asymmetric unit of the structure contains two independent molecules. The conformations of the N—H bonds in the amide segments are anti to the meta–chloro atoms in the benzene rings of both the molecules, in contrast to the syn conformation observed between the N—H bond and ortho–chloro atom in N-(2-Chloro-4-methylphenyl)-succinamic acid (I) (Chaithanya et al., 2012).

Further, the conformations of the amide oxygen and the carboxyl oxygen of the acid segments are anti to each other and both are anti to the H atoms on the adjacent –CH2 groups.

The CO and O—H bonds of the acid groups are in syn position to each other, similar to that observed in (I).

The dihedral angles between the phenyl ring and the amide group in the two independent molecules are 40.58 (22)° and 44.93 (27)°, compared to the value of 48.39 (12)° in (I).

In the structure, the pairs of O—H···O and N—H···O intermolecular hydrogen bonds pack the molecules into infinite chains (Table 1, Fig.2).

Related literature top

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000); Chaithanya et al. (2012). For N-(aryl)-methanesulfonamides, see: Gowda et al. (2007). For N-chloroarylamides, see: Gowda et al. (2003); Jyothi & Gowda (2004). For N-bromoarylsulfonamides, see: Usha & Gowda (2006).

Experimental top

The solution of succinic anhydride (0.01 mole) in toluene (25 ml) was treated dropwise with the solution of 3-chloro,4-methylaniline (0.01 mole) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about one hour and set aside for an additional hour at room temperature for completion of the reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted 3-chloro-4-methyl- aniline. The resultant title compound was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. It was recrystallized to constant melting point from ethanol. The purity of the compound was checked and characterized by its infrared and NMR spectra.

Needle like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.

Refinement top

The H atoms of the NH group and the OH group were located in a difference map and later restrained to N—H = 0.86 (2) Å and O—H = 0.82 (2) Å, respectively. The other H atoms were positioned with idealized geometry using a riding model with aromatic C—H = 0.93 Å and methylene C—H = 0.97 Å. All H atoms were refined with isotropic displacement parameters set at 1.2 Ueq(C-aromatic, N) and 1.5 Ueq(C-methyl).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
N-(3-Chloro-4-methylphenyl)succinamic acid top
Crystal data top
C11H12ClNO3Z = 4
Mr = 241.67F(000) = 504
Triclinic, P1Dx = 1.414 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8788 (9) ÅCell parameters from 1965 reflections
b = 7.9713 (9) Åθ = 2.6–27.8°
c = 21.119 (3) ŵ = 0.33 mm1
α = 86.76 (1)°T = 293 K
β = 86.48 (1)°Needle, colourless
γ = 79.45 (1)°0.42 × 0.14 × 0.08 mm
V = 1135.1 (3) Å3
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
4066 independent reflections
Radiation source: fine-focus sealed tube2649 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Rotation method data acquisition using ω and phi scansθmax = 25.3°, θmin = 2.6°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 87
Tmin = 0.875, Tmax = 0.974k = 95
6890 measured reflectionsl = 2524
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)] = 0.083Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.26 w = 1/[σ2(Fo2) + (0.0164P)2 + 2.1147P]
where P = (Fo2 + 2Fc2)/3
4066 reflections(Δ/σ)max < 0.001
303 parametersΔρmax = 0.23 e Å3
4 restraintsΔρmin = 0.29 e Å3
Crystal data top
C11H12ClNO3γ = 79.45 (1)°
Mr = 241.67V = 1135.1 (3) Å3
Triclinic, P1Z = 4
a = 6.8788 (9) ÅMo Kα radiation
b = 7.9713 (9) ŵ = 0.33 mm1
c = 21.119 (3) ÅT = 293 K
α = 86.76 (1)°0.42 × 0.14 × 0.08 mm
β = 86.48 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
4066 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
2649 reflections with I > 2σ(I)
Tmin = 0.875, Tmax = 0.974Rint = 0.028
6890 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0834 restraints
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.26Δρmax = 0.23 e Å3
4066 reflectionsΔρmin = 0.29 e Å3
303 parameters
Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C10.9701 (7)0.4350 (5)0.2737 (2)0.0373 (11)
C20.8270 (7)0.4875 (6)0.3209 (2)0.0395 (11)
H20.69960.46470.31920.047*
C30.8765 (7)0.5746 (6)0.3707 (2)0.0406 (11)
C41.0621 (8)0.6124 (6)0.3758 (2)0.0462 (12)
C51.2006 (7)0.5579 (6)0.3278 (2)0.0508 (13)
H51.32800.58030.32970.061*
C61.1575 (7)0.4713 (6)0.2771 (2)0.0492 (13)
H61.25450.43760.24540.059*
C70.7569 (7)0.3702 (6)0.1926 (2)0.0442 (12)
C80.7444 (8)0.2452 (6)0.1422 (2)0.0520 (14)
H8A0.85420.24590.11110.062*
H8B0.75710.13100.16180.062*
C90.5540 (8)0.2863 (7)0.1088 (3)0.0643 (16)
H9A0.44430.29250.14020.077*
H9B0.54530.39790.08720.077*
C100.5339 (9)0.1589 (7)0.0616 (3)0.0625 (16)
C111.1143 (8)0.7015 (7)0.4315 (2)0.0641 (16)
H11A1.09900.63290.46980.077*
H11B1.02820.81030.43470.077*
H11C1.24910.71800.42580.077*
N10.9276 (6)0.3407 (5)0.22252 (18)0.0444 (10)
H1N1.019 (5)0.261 (4)0.210 (2)0.053*
O10.6196 (5)0.4867 (4)0.20492 (16)0.0577 (10)
O20.6511 (6)0.0290 (5)0.0539 (2)0.0819 (14)
O30.3768 (7)0.2020 (6)0.0292 (2)0.1039 (18)
H3O0.370 (11)0.124 (6)0.006 (3)0.125*
Cl10.6908 (2)0.63733 (18)0.42917 (6)0.0627 (4)
C120.5122 (7)1.0684 (5)0.7315 (2)0.0391 (11)
C130.6607 (7)0.9993 (6)0.6890 (2)0.0422 (12)
H130.79191.00530.69530.051*
C140.6131 (7)0.9208 (5)0.6365 (2)0.0397 (11)
C150.4223 (7)0.9079 (6)0.6246 (2)0.0415 (11)
C160.2766 (7)0.9777 (7)0.6688 (2)0.0534 (14)
H160.14570.97020.66280.064*
C170.3185 (7)1.0581 (6)0.7213 (2)0.0473 (12)
H170.21681.10480.74970.057*
C180.7041 (8)1.1042 (7)0.8223 (2)0.0573 (15)
C190.7225 (8)1.2230 (7)0.8742 (3)0.0707 (18)
H19A0.64361.33440.86450.085*
H19B0.66961.17900.91410.085*
C200.9289 (9)1.2424 (8)0.8816 (3)0.0722 (18)
H20A0.97961.29070.84220.087*
H20B1.00861.13030.88930.087*
C210.9521 (10)1.3530 (7)0.9343 (3)0.0619 (16)
C220.3714 (8)0.8265 (7)0.5666 (2)0.0644 (16)
H22A0.44270.71120.56550.077*
H22B0.40720.89030.52920.077*
H22C0.23170.82610.56820.077*
N20.5543 (6)1.1566 (5)0.78445 (19)0.0485 (11)
H2N0.485 (6)1.254 (4)0.790 (2)0.058*
O40.8183 (7)0.9688 (5)0.8168 (2)0.0951 (17)
O50.8321 (7)1.3876 (6)0.9774 (2)0.0946 (16)
O61.1205 (9)1.4050 (7)0.9300 (2)0.1004 (16)
H6O1.122 (11)1.457 (8)0.963 (2)0.121*
Cl20.8053 (2)0.84014 (18)0.58273 (6)0.0599 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.038 (3)0.036 (3)0.037 (2)0.001 (2)0.008 (2)0.010 (2)
C20.038 (3)0.042 (3)0.040 (3)0.007 (2)0.007 (2)0.009 (2)
C30.044 (3)0.038 (3)0.038 (3)0.001 (2)0.005 (2)0.011 (2)
C40.056 (3)0.040 (3)0.045 (3)0.009 (2)0.013 (2)0.006 (2)
C50.040 (3)0.056 (3)0.059 (3)0.012 (2)0.009 (2)0.012 (3)
C60.046 (3)0.056 (3)0.044 (3)0.000 (2)0.001 (2)0.015 (2)
C70.051 (3)0.040 (3)0.040 (3)0.001 (2)0.006 (2)0.014 (2)
C80.068 (4)0.038 (3)0.048 (3)0.004 (2)0.020 (3)0.019 (2)
C90.057 (4)0.069 (4)0.068 (4)0.001 (3)0.020 (3)0.037 (3)
C100.063 (4)0.064 (4)0.063 (4)0.002 (3)0.020 (3)0.032 (3)
C110.068 (4)0.072 (4)0.059 (3)0.017 (3)0.017 (3)0.025 (3)
N10.044 (3)0.042 (2)0.046 (2)0.0057 (19)0.0109 (19)0.0200 (19)
O10.053 (2)0.055 (2)0.061 (2)0.0148 (18)0.0208 (17)0.0312 (18)
O20.081 (3)0.067 (3)0.097 (3)0.016 (2)0.042 (2)0.051 (2)
O30.088 (3)0.095 (3)0.126 (4)0.029 (3)0.065 (3)0.073 (3)
Cl10.0659 (9)0.0708 (9)0.0511 (8)0.0068 (7)0.0061 (6)0.0275 (7)
C120.047 (3)0.030 (2)0.041 (3)0.002 (2)0.009 (2)0.010 (2)
C130.030 (3)0.049 (3)0.048 (3)0.002 (2)0.006 (2)0.014 (2)
C140.041 (3)0.034 (3)0.043 (3)0.001 (2)0.003 (2)0.007 (2)
C150.041 (3)0.044 (3)0.042 (3)0.012 (2)0.004 (2)0.005 (2)
C160.034 (3)0.072 (4)0.057 (3)0.014 (3)0.008 (2)0.010 (3)
C170.038 (3)0.055 (3)0.048 (3)0.003 (2)0.001 (2)0.011 (2)
C180.059 (4)0.055 (3)0.057 (3)0.006 (3)0.017 (3)0.028 (3)
C190.068 (4)0.072 (4)0.070 (4)0.010 (3)0.024 (3)0.045 (3)
C200.082 (5)0.066 (4)0.071 (4)0.006 (3)0.019 (3)0.040 (3)
C210.073 (4)0.061 (4)0.055 (4)0.011 (3)0.021 (3)0.019 (3)
C220.066 (4)0.082 (4)0.054 (3)0.029 (3)0.010 (3)0.017 (3)
N20.049 (3)0.041 (2)0.053 (2)0.0089 (19)0.011 (2)0.024 (2)
O40.105 (3)0.072 (3)0.097 (3)0.048 (3)0.062 (3)0.058 (2)
O50.109 (4)0.111 (4)0.077 (3)0.045 (3)0.005 (3)0.053 (3)
O60.121 (4)0.126 (4)0.071 (3)0.053 (3)0.001 (3)0.049 (3)
Cl20.0528 (8)0.0685 (9)0.0563 (8)0.0000 (7)0.0034 (6)0.0261 (7)
Geometric parameters (Å, º) top
C1—C61.378 (6)C12—C131.375 (6)
C1—C21.384 (6)C12—C171.380 (6)
C1—N11.424 (5)C12—N21.426 (5)
C2—C31.385 (6)C13—C141.387 (6)
C2—H20.9300C13—H130.9300
C3—C41.376 (7)C14—C151.375 (6)
C3—Cl11.746 (4)C14—Cl21.743 (4)
C4—C51.380 (7)C15—C161.387 (6)
C4—C111.502 (6)C15—C221.507 (6)
C5—C61.382 (6)C16—C171.383 (6)
C5—H50.9300C16—H160.9300
C6—H60.9300C17—H170.9300
C7—O11.223 (5)C18—O41.220 (6)
C7—N11.344 (6)C18—N21.334 (6)
C7—C81.516 (6)C18—C191.515 (6)
C8—C91.499 (7)C19—C201.475 (8)
C8—H8A0.9700C19—H19A0.9700
C8—H8B0.9700C19—H19B0.9700
C9—C101.492 (6)C20—C211.491 (7)
C9—H9A0.9700C20—H20A0.9700
C9—H9B0.9700C20—H20B0.9700
C10—O21.202 (6)C21—O51.200 (7)
C10—O31.297 (6)C21—O61.297 (7)
C11—H11A0.9600C22—H22A0.9600
C11—H11B0.9600C22—H22B0.9600
C11—H11C0.9600C22—H22C0.9600
N1—H1N0.853 (19)N2—H2N0.843 (19)
O3—H3O0.83 (2)O6—H6O0.83 (2)
C6—C1—C2119.4 (4)C13—C12—C17119.5 (4)
C6—C1—N1119.7 (4)C13—C12—N2121.0 (4)
C2—C1—N1120.9 (4)C17—C12—N2119.5 (4)
C1—C2—C3118.9 (4)C12—C13—C14119.4 (4)
C1—C2—H2120.5C12—C13—H13120.3
C3—C2—H2120.5C14—C13—H13120.3
C4—C3—C2123.3 (4)C15—C14—C13123.0 (4)
C4—C3—Cl1119.6 (3)C15—C14—Cl2119.1 (3)
C2—C3—Cl1117.1 (4)C13—C14—Cl2117.8 (4)
C3—C4—C5116.0 (4)C14—C15—C16116.0 (4)
C3—C4—C11122.3 (5)C14—C15—C22122.7 (4)
C5—C4—C11121.6 (5)C16—C15—C22121.3 (5)
C4—C5—C6122.7 (5)C17—C16—C15122.5 (5)
C4—C5—H5118.7C17—C16—H16118.7
C6—C5—H5118.7C15—C16—H16118.7
C1—C6—C5119.7 (4)C12—C17—C16119.6 (4)
C1—C6—H6120.1C12—C17—H17120.2
C5—C6—H6120.1C16—C17—H17120.2
O1—C7—N1123.6 (4)O4—C18—N2123.1 (4)
O1—C7—C8121.7 (4)O4—C18—C19121.3 (5)
N1—C7—C8114.7 (4)N2—C18—C19115.6 (4)
C9—C8—C7112.8 (4)C20—C19—C18112.7 (5)
C9—C8—H8A109.0C20—C19—H19A109.1
C7—C8—H8A109.0C18—C19—H19A109.1
C9—C8—H8B109.0C20—C19—H19B109.1
C7—C8—H8B109.0C18—C19—H19B109.1
H8A—C8—H8B107.8H19A—C19—H19B107.8
C10—C9—C8113.5 (4)C19—C20—C21113.7 (5)
C10—C9—H9A108.9C19—C20—H20A108.8
C8—C9—H9A108.9C21—C20—H20A108.8
C10—C9—H9B108.9C19—C20—H20B108.8
C8—C9—H9B108.9C21—C20—H20B108.8
H9A—C9—H9B107.7H20A—C20—H20B107.7
O2—C10—O3122.9 (5)O5—C21—O6122.6 (5)
O2—C10—C9123.8 (5)O5—C21—C20124.6 (6)
O3—C10—C9113.3 (5)O6—C21—C20112.8 (6)
C4—C11—H11A109.5C15—C22—H22A109.5
C4—C11—H11B109.5C15—C22—H22B109.5
H11A—C11—H11B109.5H22A—C22—H22B109.5
C4—C11—H11C109.5C15—C22—H22C109.5
H11A—C11—H11C109.5H22A—C22—H22C109.5
H11B—C11—H11C109.5H22B—C22—H22C109.5
C7—N1—C1125.1 (4)C18—N2—C12125.3 (4)
C7—N1—H1N118 (3)C18—N2—H2N118 (4)
C1—N1—H1N117 (3)C12—N2—H2N116 (3)
C10—O3—H3O109 (5)C21—O6—H6O105 (5)
C6—C1—C2—C30.4 (7)C17—C12—C13—C140.1 (7)
N1—C1—C2—C3178.1 (4)N2—C12—C13—C14177.3 (4)
C1—C2—C3—C40.1 (7)C12—C13—C14—C150.0 (7)
C1—C2—C3—Cl1179.8 (3)C12—C13—C14—Cl2178.3 (4)
C2—C3—C4—C50.1 (7)C13—C14—C15—C160.5 (7)
Cl1—C3—C4—C5179.8 (4)Cl2—C14—C15—C16178.8 (4)
C2—C3—C4—C11177.7 (5)C13—C14—C15—C22178.3 (5)
Cl1—C3—C4—C112.1 (7)Cl2—C14—C15—C220.0 (7)
C3—C4—C5—C60.4 (8)C14—C15—C16—C171.0 (8)
C11—C4—C5—C6178.0 (5)C22—C15—C16—C17177.8 (5)
C2—C1—C6—C50.6 (7)C13—C12—C17—C160.3 (7)
N1—C1—C6—C5177.9 (4)N2—C12—C17—C16177.8 (5)
C4—C5—C6—C10.6 (8)C15—C16—C17—C120.9 (8)
O1—C7—C8—C92.6 (8)O4—C18—C19—C2044.0 (9)
N1—C7—C8—C9178.3 (5)N2—C18—C19—C20137.0 (6)
C7—C8—C9—C10176.6 (5)C18—C19—C20—C21177.5 (5)
C8—C9—C10—O25.2 (9)C19—C20—C21—O519.0 (9)
C8—C9—C10—O3174.7 (6)C19—C20—C21—O6163.0 (6)
O1—C7—N1—C12.5 (8)O4—C18—N2—C123.1 (10)
C8—C7—N1—C1176.6 (4)C19—C18—N2—C12178.0 (5)
C6—C1—N1—C7141.8 (5)C13—C12—N2—C1844.3 (8)
C2—C1—N1—C739.7 (7)C17—C12—N2—C18138.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O4i0.85 (2)2.05 (2)2.882 (5)165 (5)
O3—H3O···O2ii0.83 (2)1.83 (2)2.654 (5)173 (7)
N2—H2N···O1iii0.84 (2)2.07 (2)2.891 (5)165 (5)
O6—H6O···O5iv0.83 (2)1.90 (3)2.703 (5)164 (7)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y, z; (iii) x+1, y+2, z+1; (iv) x+2, y+3, z+2.

Experimental details

Crystal data
Chemical formulaC11H12ClNO3
Mr241.67
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)6.8788 (9), 7.9713 (9), 21.119 (3)
α, β, γ (°)86.76 (1), 86.48 (1), 79.45 (1)
V3)1135.1 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.42 × 0.14 × 0.08
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.875, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
6890, 4066, 2649
Rint0.028
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.083, 0.159, 1.26
No. of reflections4066
No. of parameters303
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.29

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O4i0.853 (19)2.05 (2)2.882 (5)165 (5)
O3—H3O···O2ii0.83 (2)1.83 (2)2.654 (5)173 (7)
N2—H2N···O1iii0.843 (19)2.07 (2)2.891 (5)165 (5)
O6—H6O···O5iv0.83 (2)1.90 (3)2.703 (5)164 (7)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y, z; (iii) x+1, y+2, z+1; (iv) x+2, y+3, z+2.
 

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a UGC-BSR one-time grant to faculty.

References

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First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.  Google Scholar
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First citationUsha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351–359.  Web of Science CrossRef CAS Google Scholar

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