N-(3-Chloro­phen­yl)-N′-(2-methyl­phenyl)succinamide monohydrate

Saraswathi, B.S.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811014942

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1223

doi:10.1107/S1600536811014942

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N-(3-Chlorophenyl)-N′-(2-methylphenyl)succinamide monohydrate

B. S. Saraswathi,^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 8 April 2011; accepted 20 April 2011; online 29 April 2011)

In the title compound, C₁₇H₁₇ClN₂O₂·H₂O, the dihedral angles formed by the aromatic rings of the chlorobenzene and methylbenzene groups with the mean planes of the attached NH–C(O)–CH₂ fragments are 9.4 (4) and 62.9 (2)°, respectively. In the crystal, molecules are packed into layers parallel to the bc plane by O—H⋯O and N—H⋯O hydrogen-bond interactions.

Related literature

For our study on the effects of substituents on the structures of N-(aryl)amides, see: Gowda et al. (2004 ); Saraswathi et al. (2011a ,b ). For the oxidative strengths of N-chloro-N-arylsulfonamides, see: Gowda & Kumar (2003 ).

Experimental

Crystal data

C₁₇H₁₇ClN₂O₂·H₂O
M_r = 334.79
Monoclinic, P 2₁ /c
a = 14.875 (4) Å
b = 13.908 (3) Å
c = 8.088 (2) Å
β = 90.11 (2)°
V = 1673.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.44 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.900, T_max = 0.981
6273 measured reflections
3080 independent reflections
1436 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.115
wR(F²) = 0.285
S = 1.14
3080 reflections
221 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.86 (2)	2.08 (2)	2.940 (7)	175 (6)
N2—H2N⋯O2ⁱⁱ	0.86 (2)	2.25 (4)	2.991 (7)	145 (6)
O3—H31O⋯O2	0.85 (2)	2.04 (3)	2.861 (6)	163 (8)
O3—H32O⋯O1ⁱⁱⁱ	0.84 (2)	2.05 (3)	2.877 (6)	171 (9)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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 ); 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: 10.1107/S1600536811014942/rz2582sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014942/rz2582Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811014942/rz2582Isup3.cml

checkCIF report

Comment top

The amide and sulfonamide moieties are important constituents of many biologically important compounds. As a part of studying the substituent effects on the structures and other aspects of this class of compounds (Gowda & Kumar, 2003; Gowda et al., 2004; Saraswathi et al., 2011a,b), in the present work, the structure of N-(3-chlorophenyl)-N-(2-methylphenyl)-succinamide monohydrate is reported (Fig. 1). The conformations of the N—H and C═O bonds in the C—NH—C(O)—C—C—C(O)—NH—C fragment are anti to each other and the amide O atom is anti to the H atoms attached to the adjacent C atoms. Further, the conformations of the N—H bonds in the amide fragments are anti to the meta-chloro or the ortho-methyl groups in the respective adjacent benzene rings, similar to the anti conformations observed with respect to the ortho-methyl groups in N,N'-bis(2-methylphenyl)succinamide (II; Saraswathi et al., 2011a) and the meta-chloro groups in N,N'-bis(3-chlorophenyl)-succinamide (III; Saraswathi et al., 2011b).

The dihedral angle between the 3-chlorobenzene ring and the adjacent NH—C(O)—CH₂ group is 9.4 (4)° and that between the 2-methylbenzene ring and the adjacent NH—C(O)—CH₂ group is 62.9 (2)°, compared to the values of 62.1 (2)° for that between the benzene ring and the NH—C(O)—CH₂ group in the two halves of (II), and 32.8 (1)° in (III)

The torsion angles C1—N1—C7—C8 and C11—N2—C10—C9 are -173.0 (6)° and -177.9 (6)°, in contrast to the value of 69.5 (7)° for the torsion angle C7—C8—C9—C10.

In the crystal packing, molecules are linked by N1—H1N···O3, N2—H2N···O2, O3—H31O···O2 and O3—H32O···O1 hydrogen bonds (Table 1; Fig. 2) to form layers parallel to the bc plane.

Related literature top

For our study on the effects of substituents on the structures of N-(aryl)amides, see: Gowda et al. (2004); Saraswathi et al. (2011a,b). For the oxidative strengths of N-chloro-N-arylsulfonamides, see: Gowda & Kumar (2003).

Experimental top

Succinic anhydride (0.01 mol) in toluene (25 ml) was treated drop wise with o-toluidine (0.01 mol) in toluene (20 ml) with constant stirring. The resulting mixture was stirred for 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 unreacted o-toluidine. The resultant solid N-(2-methylphenyl)succinamic acid was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. The compound was recrystallized to constant melting point from ethanol. The purity of the compound was checked by elemental analysis and characterized by its infrared and NMR spectra.

The N-(2-methylphenyl)succinamic acid obtained was then treated with phosphorous oxychloride and excess of 3-chloroaniline at room temperature with constant stirring. The resultant mixture was stirred for 4 h, kept aside for additional 6 h for completion of the reaction and poured slowly into crushed ice with constant stirring. It was kept aside for a day. The resultant solid, N-(3-chlorophenyl)-N'-(2-methylphenyl)succinamide monohydrate was filtered under suction, washed thoroughly with water, with a dilute sodium hydroxide solution and finally with water. It was recrystallized to constant melting point from an acetone/chloroform (1:1 v/v) solution. The purity of the compound was checked by elemental analysis, and characterized by its infrared and NMR spectra. Needle-like colourless single crystals used for the X-ray diffraction studies were grown by slow evaporation of an acetone/chloroform (1:1 v/v) solution at room temperature.

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

	Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level. The intermolecular O—H···O hydrogen bond involving the water molecule is drawn as a dashed line.
	Fig. 2. A partial packing diagram of the title compound viewed along the b axis, showing the hydrogen-bonding scheme with dashed lines.

N-(3-Chlorophenyl)-N'-(2-methylphenyl)butanediamide monohydrate top

Crystal data top

C₁₇H₁₇ClN₂O₂·H₂O	F(000) = 704
M_r = 334.79	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1620 reflections
a = 14.875 (4) Å	θ = 2.7–27.9°
b = 13.908 (3) Å	µ = 0.24 mm⁻¹
c = 8.088 (2) Å	T = 293 K
β = 90.11 (2)°	Needle, colourless
V = 1673.3 (7) Å³	0.44 × 0.12 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3080 independent reflections
Radiation source: fine-focus sealed tube	1436 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
Rotation method data acquisition using ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −18→14
T_min = 0.900, T_max = 0.981	k = −16→16
6273 measured reflections	l = −9→8

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)] = 0.115	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.285	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.104P)² + 1.4616P] where P = (F_o² + 2F_c²)/3
3080 reflections	(Δ/σ)_max = 0.010
221 parameters	Δρ_max = 0.66 e Å⁻³
5 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₇H₁₇ClN₂O₂·H₂O	V = 1673.3 (7) Å³
M_r = 334.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.875 (4) Å	µ = 0.24 mm⁻¹
b = 13.908 (3) Å	T = 293 K
c = 8.088 (2) Å	0.44 × 0.12 × 0.08 mm
β = 90.11 (2)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3080 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1436 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.981	R_int = 0.074
6273 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.115	5 restraints
wR(F²) = 0.285	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.66 e Å⁻³
3080 reflections	Δρ_min = −0.27 e Å⁻³
221 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

	x	y	z	U_iso*/U_eq
Cl1	0.24505 (16)	0.43031 (14)	0.5534 (3)	0.0888 (8)
O1	0.4988 (3)	0.2577 (3)	0.2806 (6)	0.0588 (13)
O2	0.6939 (3)	0.1531 (3)	0.3675 (5)	0.0509 (12)
N1	0.4157 (4)	0.1301 (4)	0.3620 (7)	0.0526 (14)
H1N	0.414 (4)	0.0680 (15)	0.367 (8)	0.063*
N2	0.7588 (4)	0.2301 (4)	0.1544 (6)	0.0511 (15)
H2N	0.757 (4)	0.246 (4)	0.052 (3)	0.061*
C1	0.3450 (4)	0.1731 (5)	0.4498 (8)	0.0480 (17)
C2	0.3334 (4)	0.2716 (4)	0.4599 (8)	0.0497 (17)
H2	0.3746	0.3134	0.4120	0.060*
C3	0.2595 (5)	0.3062 (5)	0.5426 (9)	0.0571 (19)
C4	0.1978 (5)	0.2489 (6)	0.6174 (9)	0.0622 (19)
H4	0.1488	0.2749	0.6729	0.075*
C5	0.2105 (5)	0.1503 (5)	0.6079 (10)	0.072 (2)
H5	0.1695	0.1093	0.6582	0.087*
C6	0.2826 (5)	0.1127 (5)	0.5254 (9)	0.062 (2)
H6	0.2900	0.0464	0.5198	0.074*
C7	0.4836 (4)	0.1708 (5)	0.2793 (8)	0.0446 (16)
C8	0.5394 (4)	0.1008 (5)	0.1842 (8)	0.0542 (18)
H8A	0.5022	0.0715	0.0994	0.065*
H8B	0.5591	0.0502	0.2585	0.065*
C9	0.6221 (5)	0.1455 (5)	0.1022 (8)	0.0540 (18)
H9A	0.6479	0.0991	0.0263	0.065*
H9B	0.6033	0.2009	0.0380	0.065*
C10	0.6931 (4)	0.1764 (4)	0.2227 (8)	0.0404 (15)
C11	0.8362 (5)	0.2665 (5)	0.2395 (7)	0.0478 (17)
C12	0.9000 (5)	0.2044 (5)	0.3062 (8)	0.059 (2)
C13	0.9760 (5)	0.2453 (7)	0.3794 (9)	0.073 (2)
H13	1.0195	0.2058	0.4264	0.087*
C14	0.9870 (6)	0.3428 (8)	0.3827 (10)	0.083 (3)
H14	1.0384	0.3685	0.4312	0.100*
C15	0.9247 (6)	0.4031 (6)	0.3169 (11)	0.081 (3)
H15	0.9335	0.4693	0.3196	0.097*
C16	0.8483 (6)	0.3649 (5)	0.2460 (9)	0.066 (2)
H16	0.8047	0.4056	0.2024	0.079*
C17	0.8932 (6)	0.0992 (6)	0.2956 (10)	0.087 (3)
H17A	0.8438	0.0775	0.3621	0.131*
H17B	0.9479	0.0708	0.3352	0.131*
H17C	0.8834	0.0807	0.1827	0.131*
O3	0.5938 (4)	0.0811 (3)	0.6426 (6)	0.0690 (15)
H31O	0.614 (5)	0.098 (5)	0.549 (5)	0.104*
H32O	0.561 (5)	0.125 (4)	0.679 (8)	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0963 (17)	0.0478 (12)	0.1224 (19)	0.0147 (12)	0.0074 (14)	−0.0092 (12)
O1	0.062 (3)	0.036 (3)	0.079 (3)	−0.011 (2)	0.007 (2)	−0.005 (2)
O2	0.054 (3)	0.055 (3)	0.044 (3)	0.002 (2)	0.006 (2)	0.005 (2)
N1	0.047 (3)	0.036 (3)	0.074 (4)	−0.002 (3)	0.006 (3)	0.004 (3)
N2	0.059 (4)	0.056 (4)	0.039 (3)	0.004 (3)	0.006 (3)	0.005 (3)
C1	0.046 (4)	0.046 (4)	0.052 (4)	−0.007 (3)	−0.006 (3)	0.001 (3)
C2	0.044 (4)	0.042 (4)	0.062 (4)	−0.001 (3)	−0.001 (4)	−0.001 (3)
C3	0.059 (5)	0.048 (4)	0.065 (4)	−0.001 (4)	−0.006 (4)	−0.008 (4)
C4	0.053 (4)	0.069 (5)	0.066 (5)	0.005 (4)	0.007 (4)	−0.003 (4)
C5	0.067 (5)	0.059 (5)	0.091 (6)	−0.009 (4)	0.017 (5)	0.003 (4)
C6	0.064 (5)	0.048 (4)	0.075 (5)	−0.004 (4)	0.013 (4)	−0.001 (4)
C7	0.040 (4)	0.042 (4)	0.052 (4)	−0.002 (3)	−0.002 (3)	−0.002 (3)
C8	0.055 (4)	0.040 (4)	0.067 (4)	−0.007 (3)	−0.006 (4)	−0.011 (3)
C9	0.068 (5)	0.048 (4)	0.046 (4)	0.004 (4)	0.003 (4)	−0.010 (3)
C10	0.049 (4)	0.036 (3)	0.036 (4)	0.004 (3)	0.004 (3)	−0.007 (3)
C11	0.047 (4)	0.058 (4)	0.039 (4)	0.002 (4)	0.002 (3)	−0.002 (3)
C12	0.062 (5)	0.058 (5)	0.056 (4)	0.002 (4)	0.019 (4)	0.002 (4)
C13	0.046 (5)	0.098 (7)	0.073 (5)	0.002 (5)	0.000 (4)	−0.008 (5)
C14	0.057 (5)	0.111 (8)	0.082 (6)	−0.019 (6)	0.007 (5)	−0.016 (6)
C15	0.082 (6)	0.061 (5)	0.099 (7)	−0.014 (5)	0.008 (6)	−0.006 (5)
C16	0.069 (5)	0.051 (5)	0.076 (5)	−0.009 (4)	0.007 (4)	−0.006 (4)
C17	0.089 (7)	0.071 (6)	0.102 (7)	0.010 (5)	0.014 (5)	0.000 (5)
O3	0.091 (4)	0.034 (3)	0.083 (4)	0.008 (3)	0.028 (3)	0.008 (3)

Geometric parameters (Å, º) top

Cl1—C3	1.742 (7)	C8—H8A	0.9700
O1—C7	1.230 (7)	C8—H8B	0.9700
O2—C10	1.215 (7)	C9—C10	1.499 (9)
N1—C7	1.338 (8)	C9—H9A	0.9700
N1—C1	1.404 (8)	C9—H9B	0.9700
N1—H1N	0.86 (2)	C11—C16	1.381 (9)
N2—C10	1.350 (8)	C11—C12	1.391 (9)
N2—C11	1.432 (8)	C12—C13	1.396 (10)
N2—H2N	0.86 (2)	C12—C17	1.469 (10)
C1—C2	1.384 (9)	C13—C14	1.366 (11)
C1—C6	1.393 (9)	C13—H13	0.9300
C2—C3	1.375 (9)	C14—C15	1.357 (11)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.358 (9)	C15—C16	1.378 (11)
C4—C5	1.386 (9)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.368 (10)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—C8	1.494 (9)	O3—H31O	0.85 (2)
C8—C9	1.531 (9)	O3—H32O	0.84 (2)

C7—N1—C1	129.7 (6)	C10—C9—H9A	108.9
C7—N1—H1N	118 (4)	C8—C9—H9A	108.8
C1—N1—H1N	113 (4)	C10—C9—H9B	108.8
C10—N2—C11	125.5 (5)	C8—C9—H9B	108.8
C10—N2—H2N	121 (5)	H9A—C9—H9B	107.7
C11—N2—H2N	113 (5)	O2—C10—N2	122.4 (6)
C2—C1—C6	119.2 (6)	O2—C10—C9	123.8 (6)
C2—C1—N1	123.0 (6)	N2—C10—C9	113.7 (5)
C6—C1—N1	117.8 (6)	C16—C11—C12	120.8 (7)
C3—C2—C1	118.3 (6)	C16—C11—N2	118.2 (6)
C3—C2—H2	120.8	C12—C11—N2	120.9 (6)
C1—C2—H2	120.8	C11—C12—C13	117.6 (7)
C4—C3—C2	123.6 (7)	C11—C12—C17	123.3 (7)
C4—C3—Cl1	118.4 (6)	C13—C12—C17	119.1 (8)
C2—C3—Cl1	118.0 (6)	C14—C13—C12	120.6 (8)
C3—C4—C5	117.6 (7)	C14—C13—H13	119.7
C3—C4—H4	121.2	C12—C13—H13	119.7
C5—C4—H4	121.2	C15—C14—C13	121.6 (9)
C6—C5—C4	120.8 (7)	C15—C14—H14	119.2
C6—C5—H5	119.6	C13—C14—H14	119.2
C4—C5—H5	119.6	C14—C15—C16	119.1 (8)
C5—C6—C1	120.5 (7)	C14—C15—H15	120.4
C5—C6—H6	119.7	C16—C15—H15	120.4
C1—C6—H6	119.7	C15—C16—C11	120.3 (8)
O1—C7—N1	123.5 (6)	C15—C16—H16	119.8
O1—C7—C8	122.8 (6)	C11—C16—H16	119.8
N1—C7—C8	113.7 (6)	C12—C17—H17A	109.5
C7—C8—C9	114.0 (5)	C12—C17—H17B	109.5
C7—C8—H8A	108.8	H17A—C17—H17B	109.5
C9—C8—H8A	108.8	C12—C17—H17C	109.5
C7—C8—H8B	108.8	H17A—C17—H17C	109.5
C9—C8—H8B	108.8	H17B—C17—H17C	109.5
H8A—C8—H8B	107.7	H31O—O3—H32O	108 (3)
C10—C9—C8	113.6 (5)

C7—N1—C1—C2	2.1 (11)	C11—N2—C10—O2	−0.2 (10)
C7—N1—C1—C6	−180.0 (7)	C11—N2—C10—C9	−177.8 (6)
C6—C1—C2—C3	−1.0 (10)	C8—C9—C10—O2	13.0 (9)
N1—C1—C2—C3	177.0 (6)	C8—C9—C10—N2	−169.4 (5)
C1—C2—C3—C4	1.1 (10)	C10—N2—C11—C16	−119.5 (7)
C1—C2—C3—Cl1	−179.5 (5)	C10—N2—C11—C12	63.9 (8)
C2—C3—C4—C5	−0.4 (11)	C16—C11—C12—C13	0.1 (9)
Cl1—C3—C4—C5	−179.9 (6)	N2—C11—C12—C13	176.6 (6)
C3—C4—C5—C6	−0.2 (12)	C16—C11—C12—C17	−176.8 (7)
C4—C5—C6—C1	0.3 (12)	N2—C11—C12—C17	−0.2 (9)
C2—C1—C6—C5	0.3 (11)	C11—C12—C13—C14	−0.8 (10)
N1—C1—C6—C5	−177.7 (7)	C17—C12—C13—C14	176.2 (7)
C1—N1—C7—O1	6.9 (11)	C12—C13—C14—C15	0.6 (13)
C1—N1—C7—C8	−173.0 (6)	C13—C14—C15—C16	0.4 (13)
O1—C7—C8—C9	5.4 (9)	C14—C15—C16—C11	−1.2 (12)
N1—C7—C8—C9	−174.7 (6)	C12—C11—C16—C15	0.9 (10)
C7—C8—C9—C10	69.5 (7)	N2—C11—C16—C15	−175.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.86 (2)	2.08 (2)	2.940 (7)	175 (6)
N2—H2N···O2ⁱⁱ	0.86 (2)	2.25 (4)	2.991 (7)	145 (6)
O3—H31O···O2	0.85 (2)	2.04 (3)	2.861 (6)	163 (8)
O3—H32O···O1ⁱⁱⁱ	0.84 (2)	2.05 (3)	2.877 (6)	171 (9)

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇ClN₂O₂·H₂O
M_r	334.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.875 (4), 13.908 (3), 8.088 (2)
β (°)	90.11 (2)
V (Å³)	1673.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.44 × 0.12 × 0.08

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	0.900, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	6273, 3080, 1436
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.115, 0.285, 1.14
No. of reflections	3080
No. of parameters	221
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.27

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
N1—H1N···O3ⁱ	0.86 (2)	2.08 (2)	2.940 (7)	175 (6)
N2—H2N···O2ⁱⁱ	0.86 (2)	2.25 (4)	2.991 (7)	145 (6)
O3—H31O···O2	0.85 (2)	2.04 (3)	2.861 (6)	163 (8)
O3—H32O···O1ⁱⁱⁱ	0.84 (2)	2.05 (3)	2.877 (6)	171 (9)

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

Acknowledgements

BSS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement programme.

References

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