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

Chaithanya, U.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536812024567

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2003

https://doi.org/10.1107/S1600536812024567

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

U. Chaithanya,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^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 25 May 2012; accepted 29 May 2012; online 13 June 2012)

The title compound, C₁₁H₁₂ClNO₃, crystallizes with two independent molecules in the asymmetric unit in which the dihedral angles between the benzene ring and the amide group are 55.0 (2) and 28.2 (3)°. The two independent molecules are linked by an N—H⋯O hydrogen bond. In the crystal, molecules form inversion dimers via pairs of O—H⋯O hydrogen bonds. These dimers are linked into sheets parallel to (11-3) via 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 ); Chaithanya et al. (2012 ), of N-chloroarylamides, see: Gowda & Rao (1989 ); Jyothi & Gowda (2004 ) and of N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983 ); Usha & Gowda (2006 ).

Experimental

Crystal data

C₁₁H₁₂ClNO₃
M_r = 241.67
Triclinic, $[P \overline 1]$
a = 6.6253 (8) Å
b = 7.9634 (9) Å
c = 21.545 (3) Å
α = 88.57 (1)°
β = 81.99 (1)°
γ = 84.25 (1)°
V = 1119.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 293 K
0.48 × 0.16 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.857, T_max = 0.990
6984 measured reflections
3864 independent reflections
2640 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.090
wR(F²) = 0.155
S = 1.33
3864 reflections
303 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O2ⁱ	0.82 (2)	1.85 (2)	2.668 (5)	176 (7)
N1—H1N⋯O4ⁱⁱ	0.86 (2)	2.09 (2)	2.934 (5)	169 (5)
O6—H6O⋯O5ⁱⁱⁱ	0.82 (2)	1.86 (2)	2.685 (6)	177 (8)
N2—H2N⋯O1	0.85 (2)	2.12 (2)	2.944 (6)	163 (5)
Symmetry codes: (i) -x+1, -y, -z; (ii) x+1, y-1, z; (iii) -x, -y+1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812024567/bt5936sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024567/bt5936Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812024567/bt5936Isup3.cml

checkCIF report

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-chloroarylsulfonamides (Gowda & Rao, 1989; Jyothi & Gowda, 2004) and N-bromoaryl- sulfonamides (Gowda & Mahadevappa, 1983; Usha & Gowda, 2006), in the present work, the crystal structure of N-(4-Chloro-3-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–methyl groups in the benzene rings of both the molecules, similar to the anti conformation observed between the N—H bond and meta–chloro atoms in N-(3-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 C═O 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 55.03 (22)° and 28.19 (31)°, compared to the values of 40.58 (22)° and 44.93 (27)° in (I).

In the crystal, the molecules form centrosymmetric dimers via O—H···O hydrogen bonds. These dimers are linked into sheets parallel to (1 1 -3) via N—H···O hydrogen bonds. (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), of N-chloroarylamides, see: Gowda & Rao (1989); Jyothi & Gowda (2004) and of N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983); Usha & Gowda (2006).

Experimental top

The solution of succinic anhydride (0.01 mole) in toluene (25 ml) was treated dropwise with the solution of 4-chloro-3-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 4-chloro-3-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.

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

Structure description top

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 C═O 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 55.03 (22)° and 28.19 (31)°, compared to the values of 40.58 (22)° and 44.93 (27)° in (I).

In the crystal, the molecules form centrosymmetric dimers via O—H···O hydrogen bonds. These dimers are linked into sheets parallel to (1 1 -3) via N—H···O hydrogen bonds. (Table 1, Fig. 2).

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), of N-chloroarylamides, see: Gowda & Rao (1989); Jyothi & Gowda (2004) and of N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983); Usha & Gowda (2006).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (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

	Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

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

Crystal data top

C₁₁H₁₂ClNO₃	Z = 4
M_r = 241.67	F(000) = 504
Triclinic, P1	D_x = 1.433 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6253 (8) Å	Cell parameters from 1701 reflections
b = 7.9634 (9) Å	θ = 2.6–27.4°
c = 21.545 (3) Å	µ = 0.33 mm⁻¹
α = 88.57 (1)°	T = 293 K
β = 81.99 (1)°	Plate, colourless
γ = 84.25 (1)°	0.48 × 0.16 × 0.03 mm
V = 1119.9 (2) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3864 independent reflections
Radiation source: fine-focus sealed tube	2640 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Rotation method data acquisition using ω and phi scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −7→7
T_min = 0.857, T_max = 0.990	k = −9→8
6984 measured reflections	l = −23→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.090	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.33	w = 1/[σ²(F_o²) + (0.0064P)² + 2.5267P] where P = (F_o² + 2F_c²)/3
3864 reflections	(Δ/σ)_max < 0.001
303 parameters	Δρ_max = 0.35 e Å⁻³
4 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₁H₁₂ClNO₃	γ = 84.25 (1)°
M_r = 241.67	V = 1119.9 (2) Å³
Triclinic, P1	Z = 4
a = 6.6253 (8) Å	Mo Kα radiation
b = 7.9634 (9) Å	µ = 0.33 mm⁻¹
c = 21.545 (3) Å	T = 293 K
α = 88.57 (1)°	0.48 × 0.16 × 0.03 mm
β = 81.99 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3864 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2640 reflections with I > 2σ(I)
T_min = 0.857, T_max = 0.990	R_int = 0.027
6984 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.090	4 restraints
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.33	Δρ_max = 0.35 e Å⁻³
3864 reflections	Δρ_min = −0.29 e Å⁻³
303 parameters

Special details top

Experimental. Absorption correction: 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

	x	y	z	U_iso*/U_eq
Cl1	1.1028 (3)	0.7244 (2)	0.43623 (7)	0.0669 (5)
O1	0.6519 (6)	0.5020 (5)	0.19988 (18)	0.0599 (12)
O2	0.6714 (7)	0.0487 (6)	0.0438 (2)	0.0788 (15)
O3	0.3608 (7)	0.1779 (6)	0.0426 (2)	0.0824 (15)
H3O	0.352 (11)	0.105 (6)	0.017 (3)	0.099*
N1	0.9291 (7)	0.3357 (5)	0.2222 (2)	0.0454 (12)
H1N	1.017 (6)	0.251 (5)	0.212 (2)	0.055*
C1	0.9694 (8)	0.4313 (6)	0.2738 (2)	0.0394 (13)
C2	0.8186 (8)	0.4669 (6)	0.3242 (2)	0.0404 (13)
H2	0.6905	0.4290	0.3238	0.049*
C3	0.8529 (8)	0.5574 (6)	0.3753 (2)	0.0380 (12)
C4	1.0473 (8)	0.6116 (6)	0.3735 (2)	0.0402 (13)
C5	1.1991 (8)	0.5761 (7)	0.3242 (2)	0.0473 (14)
H5	1.3276	0.6130	0.3247	0.057*
C6	1.1619 (8)	0.4854 (7)	0.2735 (2)	0.0464 (14)
H6	1.2643	0.4614	0.2399	0.056*
C7	0.7719 (8)	0.3752 (7)	0.1897 (2)	0.0409 (13)
C8	0.7563 (9)	0.2520 (7)	0.1387 (3)	0.0535 (16)
H8A	0.8685	0.2620	0.1051	0.064*
H8B	0.7703	0.1380	0.1556	0.064*
C9	0.5581 (9)	0.2808 (7)	0.1124 (3)	0.0561 (16)
H9A	0.5458	0.3940	0.0948	0.067*
H9B	0.4461	0.2737	0.1462	0.067*
C10	0.5379 (10)	0.1570 (8)	0.0627 (3)	0.0557 (16)
C11	0.6861 (9)	0.5963 (7)	0.4295 (2)	0.0574 (16)
H11A	0.5651	0.5470	0.4223	0.069*
H11B	0.6561	0.7163	0.4333	0.069*
H11C	0.7308	0.5502	0.4675	0.069*
Cl2	0.6698 (2)	1.1376 (2)	0.44331 (7)	0.0594 (4)
O4	0.1817 (6)	1.0173 (5)	0.19059 (18)	0.0632 (12)
O5	0.1879 (7)	0.5752 (6)	0.0324 (2)	0.0846 (16)
O6	−0.1414 (8)	0.6470 (7)	0.0550 (2)	0.0920 (17)
H6O	−0.157 (11)	0.576 (7)	0.029 (3)	0.110*
N2	0.4570 (7)	0.8506 (5)	0.2130 (2)	0.0428 (11)
H2N	0.531 (7)	0.759 (4)	0.204 (2)	0.051*
C12	0.5057 (8)	0.9318 (6)	0.2666 (2)	0.0354 (12)
C13	0.3572 (8)	1.0248 (6)	0.3070 (2)	0.0414 (13)
H13	0.2243	1.0431	0.2973	0.050*
C14	0.4031 (8)	1.0913 (6)	0.3619 (2)	0.0372 (12)
C15	0.6025 (8)	1.0644 (6)	0.3742 (2)	0.0397 (13)
C16	0.7513 (8)	0.9745 (7)	0.3338 (2)	0.0477 (14)
H16	0.8849	0.9587	0.3430	0.057*
C17	0.7044 (8)	0.9074 (7)	0.2796 (2)	0.0446 (14)
H17	0.8054	0.8468	0.2524	0.054*
C18	0.3015 (8)	0.8908 (7)	0.1804 (2)	0.0433 (13)
C19	0.2833 (9)	0.7696 (7)	0.1289 (2)	0.0512 (15)
H19A	0.3750	0.7969	0.0917	0.061*
H19B	0.3266	0.6558	0.1420	0.061*
C20	0.0720 (9)	0.7745 (8)	0.1128 (3)	0.0642 (18)
H20A	0.0298	0.8884	0.0995	0.077*
H20B	−0.0193	0.7489	0.1503	0.077*
C21	0.0466 (10)	0.6560 (8)	0.0627 (3)	0.0535 (15)
C22	0.2383 (8)	1.1841 (7)	0.4074 (2)	0.0525 (15)
H22A	0.1150	1.2044	0.3885	0.063*
H22B	0.2824	1.2899	0.4177	0.063*
H22C	0.2127	1.1171	0.4448	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0740 (11)	0.0742 (11)	0.0584 (9)	−0.0042 (9)	−0.0273 (8)	−0.0302 (8)
O1	0.072 (3)	0.048 (2)	0.061 (3)	0.024 (2)	−0.030 (2)	−0.029 (2)
O2	0.085 (3)	0.071 (3)	0.084 (3)	0.020 (3)	−0.038 (3)	−0.052 (3)
O3	0.082 (3)	0.083 (4)	0.087 (3)	0.016 (3)	−0.041 (3)	−0.054 (3)
N1	0.050 (3)	0.042 (3)	0.043 (3)	0.016 (2)	−0.014 (2)	−0.025 (2)
C1	0.048 (3)	0.035 (3)	0.034 (3)	0.007 (3)	−0.008 (3)	−0.012 (2)
C2	0.043 (3)	0.039 (3)	0.041 (3)	−0.002 (2)	−0.011 (3)	−0.007 (2)
C3	0.044 (3)	0.038 (3)	0.030 (3)	0.008 (2)	−0.005 (2)	−0.010 (2)
C4	0.047 (3)	0.039 (3)	0.036 (3)	0.001 (3)	−0.011 (3)	−0.014 (2)
C5	0.040 (3)	0.051 (4)	0.053 (3)	−0.003 (3)	−0.016 (3)	−0.009 (3)
C6	0.044 (3)	0.051 (4)	0.043 (3)	0.004 (3)	−0.003 (3)	−0.010 (3)
C7	0.050 (3)	0.037 (3)	0.036 (3)	0.004 (3)	−0.009 (3)	−0.014 (2)
C8	0.065 (4)	0.046 (4)	0.051 (3)	0.011 (3)	−0.021 (3)	−0.024 (3)
C9	0.065 (4)	0.049 (4)	0.057 (4)	0.004 (3)	−0.019 (3)	−0.026 (3)
C10	0.072 (4)	0.051 (4)	0.048 (3)	−0.003 (3)	−0.020 (3)	−0.018 (3)
C11	0.064 (4)	0.060 (4)	0.046 (3)	0.002 (3)	0.001 (3)	−0.015 (3)
Cl2	0.0647 (10)	0.0710 (11)	0.0479 (8)	−0.0085 (8)	−0.0223 (7)	−0.0176 (7)
O4	0.077 (3)	0.053 (3)	0.062 (3)	0.029 (2)	−0.036 (2)	−0.033 (2)
O5	0.072 (3)	0.096 (4)	0.089 (3)	0.003 (3)	−0.020 (3)	−0.062 (3)
O6	0.071 (3)	0.114 (4)	0.097 (4)	0.000 (3)	−0.027 (3)	−0.070 (3)
N2	0.046 (3)	0.040 (3)	0.042 (2)	0.010 (2)	−0.012 (2)	−0.018 (2)
C12	0.040 (3)	0.030 (3)	0.036 (3)	0.001 (2)	−0.007 (2)	−0.009 (2)
C13	0.039 (3)	0.042 (3)	0.044 (3)	0.004 (2)	−0.010 (3)	−0.013 (3)
C14	0.042 (3)	0.034 (3)	0.036 (3)	−0.002 (2)	−0.007 (2)	−0.006 (2)
C15	0.051 (3)	0.039 (3)	0.031 (3)	−0.002 (3)	−0.011 (2)	−0.009 (2)
C16	0.040 (3)	0.056 (4)	0.050 (3)	0.001 (3)	−0.018 (3)	−0.008 (3)
C17	0.037 (3)	0.052 (4)	0.042 (3)	0.009 (3)	−0.002 (3)	−0.014 (3)
C18	0.050 (3)	0.040 (3)	0.040 (3)	0.007 (3)	−0.010 (3)	−0.016 (3)
C19	0.068 (4)	0.042 (3)	0.044 (3)	0.009 (3)	−0.016 (3)	−0.023 (3)
C20	0.060 (4)	0.071 (4)	0.065 (4)	0.006 (3)	−0.019 (3)	−0.043 (3)
C21	0.058 (4)	0.051 (4)	0.053 (4)	0.002 (3)	−0.017 (3)	−0.019 (3)
C22	0.055 (4)	0.058 (4)	0.042 (3)	0.011 (3)	−0.009 (3)	−0.022 (3)

Geometric parameters (Å, º) top

Cl1—C4	1.743 (5)	Cl2—C15	1.742 (5)
O1—C7	1.226 (6)	O4—C18	1.223 (6)
O2—C10	1.207 (7)	O5—C21	1.203 (6)
O3—C10	1.300 (7)	O6—C21	1.288 (7)
O3—H3O	0.82 (2)	O6—H6O	0.82 (2)
N1—C7	1.341 (6)	N2—C18	1.336 (6)
N1—C1	1.433 (6)	N2—C12	1.427 (6)
N1—H1N	0.855 (19)	N2—H2N	0.849 (19)
C1—C2	1.383 (7)	C12—C17	1.379 (7)
C1—C6	1.385 (7)	C12—C13	1.387 (6)
C2—C3	1.388 (6)	C13—C14	1.392 (6)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.393 (7)	C14—C15	1.378 (7)
C3—C11	1.508 (7)	C14—C22	1.507 (7)
C4—C5	1.371 (7)	C15—C16	1.376 (7)
C5—C6	1.388 (7)	C16—C17	1.382 (7)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.512 (6)	C18—C19	1.514 (6)
C8—C9	1.496 (7)	C19—C20	1.485 (7)
C8—H8A	0.9700	C19—H19A	0.9700
C8—H8B	0.9700	C19—H19B	0.9700
C9—C10	1.502 (7)	C20—C21	1.488 (7)
C9—H9A	0.9700	C20—H20A	0.9700
C9—H9B	0.9700	C20—H20B	0.9700
C11—H11A	0.9600	C22—H22A	0.9600
C11—H11B	0.9600	C22—H22B	0.9600
C11—H11C	0.9600	C22—H22C	0.9600

C10—O3—H3O	111 (5)	C21—O6—H6O	114 (5)
C7—N1—C1	124.2 (4)	C18—N2—C12	128.7 (4)
C7—N1—H1N	121 (4)	C18—N2—H2N	117 (4)
C1—N1—H1N	115 (4)	C12—N2—H2N	114 (4)
C2—C1—C6	120.1 (5)	C17—C12—C13	120.0 (4)
C2—C1—N1	120.4 (5)	C17—C12—N2	118.1 (4)
C6—C1—N1	119.5 (5)	C13—C12—N2	121.8 (4)
C1—C2—C3	121.9 (5)	C12—C13—C14	121.3 (5)
C1—C2—H2	119.0	C12—C13—H13	119.3
C3—C2—H2	119.0	C14—C13—H13	119.3
C2—C3—C4	116.8 (5)	C15—C14—C13	117.7 (5)
C2—C3—C11	121.1 (5)	C15—C14—C22	121.3 (4)
C4—C3—C11	122.1 (4)	C13—C14—C22	120.9 (5)
C5—C4—C3	122.1 (4)	C16—C15—C14	121.3 (4)
C5—C4—Cl1	118.4 (4)	C16—C15—Cl2	118.3 (4)
C3—C4—Cl1	119.5 (4)	C14—C15—Cl2	120.3 (4)
C4—C5—C6	120.3 (5)	C15—C16—C17	120.8 (5)
C4—C5—H5	119.8	C15—C16—H16	119.6
C6—C5—H5	119.8	C17—C16—H16	119.6
C1—C6—C5	118.8 (5)	C12—C17—C16	119.0 (5)
C1—C6—H6	120.6	C12—C17—H17	120.5
C5—C6—H6	120.6	C16—C17—H17	120.5
O1—C7—N1	122.9 (4)	O4—C18—N2	122.9 (5)
O1—C7—C8	122.5 (5)	O4—C18—C19	121.6 (5)
N1—C7—C8	114.6 (4)	N2—C18—C19	115.5 (5)
C9—C8—C7	112.8 (4)	C20—C19—C18	113.1 (4)
C9—C8—H8A	109.0	C20—C19—H19A	109.0
C7—C8—H8A	109.0	C18—C19—H19A	109.0
C9—C8—H8B	109.0	C20—C19—H19B	109.0
C7—C8—H8B	109.0	C18—C19—H19B	109.0
H8A—C8—H8B	107.8	H19A—C19—H19B	107.8
C8—C9—C10	113.5 (5)	C19—C20—C21	114.9 (5)
C8—C9—H9A	108.9	C19—C20—H20A	108.6
C10—C9—H9A	108.9	C21—C20—H20A	108.6
C8—C9—H9B	108.9	C19—C20—H20B	108.6
C10—C9—H9B	108.9	C21—C20—H20B	108.6
H9A—C9—H9B	107.7	H20A—C20—H20B	107.5
O2—C10—O3	123.6 (5)	O5—C21—O6	122.9 (5)
O2—C10—C9	123.5 (5)	O5—C21—C20	123.4 (6)
O3—C10—C9	112.9 (5)	O6—C21—C20	113.7 (5)
C3—C11—H11A	109.5	C14—C22—H22A	109.5
C3—C11—H11B	109.5	C14—C22—H22B	109.5
H11A—C11—H11B	109.5	H22A—C22—H22B	109.5
C3—C11—H11C	109.5	C14—C22—H22C	109.5
H11A—C11—H11C	109.5	H22A—C22—H22C	109.5
H11B—C11—H11C	109.5	H22B—C22—H22C	109.5

C7—N1—C1—C2	54.0 (8)	C18—N2—C12—C17	−158.1 (6)
C7—N1—C1—C6	−127.2 (6)	C18—N2—C12—C13	25.7 (9)
C6—C1—C2—C3	0.4 (8)	C17—C12—C13—C14	−1.7 (8)
N1—C1—C2—C3	179.2 (5)	N2—C12—C13—C14	174.4 (5)
C1—C2—C3—C4	0.2 (7)	C12—C13—C14—C15	1.2 (8)
C1—C2—C3—C11	179.5 (5)	C12—C13—C14—C22	−176.6 (5)
C2—C3—C4—C5	−0.8 (8)	C13—C14—C15—C16	−0.2 (8)
C11—C3—C4—C5	179.9 (5)	C22—C14—C15—C16	177.7 (5)
C2—C3—C4—Cl1	−179.4 (4)	C13—C14—C15—Cl2	−177.8 (4)
C11—C3—C4—Cl1	1.3 (7)	C22—C14—C15—Cl2	0.0 (7)
C3—C4—C5—C6	0.8 (8)	C14—C15—C16—C17	−0.4 (8)
Cl1—C4—C5—C6	179.5 (4)	Cl2—C15—C16—C17	177.3 (4)
C2—C1—C6—C5	−0.4 (8)	C13—C12—C17—C16	1.0 (8)
N1—C1—C6—C5	−179.2 (5)	N2—C12—C17—C16	−175.2 (5)
C4—C5—C6—C1	−0.2 (8)	C15—C16—C17—C12	0.0 (9)
C1—N1—C7—O1	3.0 (9)	C12—N2—C18—O4	5.3 (10)
C1—N1—C7—C8	−177.9 (5)	C12—N2—C18—C19	−175.2 (5)
O1—C7—C8—C9	−12.4 (8)	O4—C18—C19—C20	−25.0 (8)
N1—C7—C8—C9	168.6 (5)	N2—C18—C19—C20	155.5 (5)
C7—C8—C9—C10	−178.7 (5)	C18—C19—C20—C21	−179.4 (5)
C8—C9—C10—O2	−2.8 (10)	C19—C20—C21—O5	−7.9 (10)
C8—C9—C10—O3	176.6 (6)	C19—C20—C21—O6	171.8 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2ⁱ	0.82 (2)	1.85 (2)	2.668 (5)	176 (7)
N1—H1N···O4ⁱⁱ	0.86 (2)	2.09 (2)	2.934 (5)	169 (5)
O6—H6O···O5ⁱⁱⁱ	0.82 (2)	1.86 (2)	2.685 (6)	177 (8)
N2—H2N···O1	0.85 (2)	2.12 (2)	2.944 (6)	163 (5)

Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y−1, z; (iii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂ClNO₃
M_r	241.67
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.6253 (8), 7.9634 (9), 21.545 (3)
α, β, γ (°)	88.57 (1), 81.99 (1), 84.25 (1)
V (Å³)	1119.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.48 × 0.16 × 0.03

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.857, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	6984, 3864, 2640
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.090, 0.155, 1.33
No. of reflections	3864
No. of parameters	303
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −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···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2ⁱ	0.82 (2)	1.85 (2)	2.668 (5)	176 (7)
N1—H1N···O4ⁱⁱ	0.855 (19)	2.09 (2)	2.934 (5)	169 (5)
O6—H6O···O5ⁱⁱⁱ	0.82 (2)	1.86 (2)	2.685 (6)	177 (8)
N2—H2N···O1	0.849 (19)	2.12 (2)	2.944 (6)	163 (5)

Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y−1, z; (iii) −x, −y+1, −z.

Acknowledgements

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

References

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