N-(4-Methyl­phen­yl)-N′-phenyl­butane­diamide monohydrate

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

doi:10.1107/S1600536811018915

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1495

doi:10.1107/S1600536811018915

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N-(4-Methylphenyl)-N′-phenylbutanediamide 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 13 May 2011; accepted 18 May 2011; online 25 May 2011)

In the title hydrate, C₁₇H₁₈N₂O₂·H₂O, the dihedral angles formed by the aromatic rings of the benzene and methylbenzene groups with the mean planes of the attached NH—C(O)—CH₂ fragments are 12.6 (4) and 23.3 (3)°, respectively, while that between the two aromatic rings is 73.7 (2)°. In the crystal, the water molecule accepts two and makes two hydrogen bonds. The molecules are packed into layers parallel to (101) by O—H⋯O and N—H⋯O hydrogen-bonding interactions.

Related literature

For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2000 ); Saraswathi et al. (2011a ,b ) and on the structures of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ). For restrained geometry, see: Nardelli (1999 ).

Experimental

Crystal data

C₁₇H₁₈N₂O₂·H₂O
M_r = 300.35
Monoclinic, P 2₁ /n
a = 15.242 (4) Å
b = 4.905 (1) Å
c = 21.540 (5) Å
β = 102.90 (2)°
V = 1569.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.962, T_max = 0.993
5068 measured reflections
2805 independent reflections
1356 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.117
wR(F²) = 0.239
S = 1.16
2805 reflections
211 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.85 (2)	2.06 (2)	2.895 (6)	168 (6)
N2—H2N⋯O3ⁱⁱ	0.86 (2)	2.15 (2)	2.992 (6)	169 (5)
O3—H31⋯O1	0.85 (2)	1.93 (2)	2.762 (6)	165 (5)
O3—H32⋯O3ⁱⁱⁱ	0.85 (2)	2.03 (2)	2.858 (5)	166 (5)
Symmetry codes: (i) -x+2, -y, -z+1; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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/S1600536811018915/tk2744sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018915/tk2744Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018915/tk2744Isup3.cml

checkCIF report

Comment top

The amide and sulfonamide moieties are important constituents of many biologically significant compounds. As a part of a study of the substituent effects on their structures and other aspects of this class of compounds (Gowda et al., 2000, 2007; Saraswathi et al., 2011a,b), in the present work, the structure of the title compound, isolated as a monohydrate has been determined (Fig. 1). The conformation of N—H and C═ O bonds in each C—NH—C(O)—C segment is anti, similar to that observed in N,N-bis(2-methylphenyl)- succinamide (II) (Saraswathi et al., 2011a) and in N,N-bis(3-chlorophenyl)-succinamide (III) (Saraswathi et al., 2011b).

The dihedral angle between the phenyl ring and the adjacent NH—C(O)—CH₂ segment is 12.6 (4) ° and that between the 4-methylphenyl ring and the adjacent NH—C(O)—CH₂ segment is 23.3 (3) °, compared to the values of 62.1 (2) ° formed between the benzene ring and the NH—C(O)—CH₂ segment in the two halves of (II), and 32.8 (1) ° in (III). In the title compound, the dihedral angle between the two aromatic rings is 73.7 (2) °. The crystal packing is stabilized through N1—H1N···O2, N2—H2N···O3, O3—H31···O1 and O3—H32···O3 hydrogen bonding (Table 1) and results in layers as shown in Fig.2.

Related literature top

For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2000); Saraswathi et al. (2011a,b) and on the structures of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007). For restrained geometry, see: Nardelli (1999).

Experimental top

Succinic anhydride (0.01 mol) in toluene (25 ml) was treated drop wise with aniline (0.01 mol) also 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 aniline. The resultant N-(phenyl)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 N-(phenyl)succinamic acid obtained was then treated with phosphorous oxychloride and excess of p-toluidine 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-(phenyl),N-(4-methylphenyl)- succinamide monohydrate, was filtered under suction, washed thoroughly with water, dilute sodium hydroxide solution and finally with water. It was recrystallized to constant melting point from a mixture of acetone and chloroform.

Colorless needles were grown in a mixture of acetone and chloroform 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 showing atom labelling and with displacement ellipsoids drawn at the 50% probability level. The hydrogen bond is shown as a dashed line.
	Fig. 2. A partial packing diagram of the title compound viewed in projection down the b direction, showing the hydrogen bonding scheme with dashed lines.

N-(4-Methylphenyl)-N'-phenylbutanediamide monohydrate top

Crystal data top

C₁₇H₁₈N₂O₂·H₂O	F(000) = 640
M_r = 300.35	D_x = 1.271 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 897 reflections
a = 15.242 (4) Å	θ = 2.6–27.8°
b = 4.905 (1) Å	µ = 0.09 mm⁻¹
c = 21.540 (5) Å	T = 293 K
β = 102.90 (2)°	Needle, colourless
V = 1569.7 (6) Å³	0.44 × 0.12 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2805 independent reflections
Radiation source: fine-focus sealed tube	1356 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
Rotation method data acquisition using ω scans	θ_max = 25.4°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −18→15
T_min = 0.962, T_max = 0.993	k = −5→4
5068 measured reflections	l = −25→21

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)] = 0.117	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.239	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ²(F_o²) + (0.0521P)² + 3.417P] where P = (F_o² + 2F_c²)/3
2805 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.35 e Å⁻³
5 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₇H₁₈N₂O₂·H₂O	V = 1569.7 (6) Å³
M_r = 300.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.242 (4) Å	µ = 0.09 mm⁻¹
b = 4.905 (1) Å	T = 293 K
c = 21.540 (5) Å	0.44 × 0.12 × 0.08 mm
β = 102.90 (2)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2805 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1356 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.993	R_int = 0.058
5068 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.117	5 restraints
wR(F²) = 0.239	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	Δρ_max = 0.35 e Å⁻³
2805 reflections	Δρ_min = −0.31 e Å⁻³
211 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
C1	1.1172 (4)	0.2471 (13)	0.3698 (3)	0.0477 (16)
C2	1.0806 (5)	0.4142 (15)	0.3191 (3)	0.063 (2)
H2	1.0187	0.4183	0.3031	0.076*
C3	1.1363 (6)	0.5749 (17)	0.2923 (4)	0.080 (2)
H3	1.1113	0.6843	0.2576	0.096*
C4	1.2289 (6)	0.5780 (17)	0.3157 (4)	0.090 (3)
H4	1.2656	0.6879	0.2971	0.108*
C5	1.2648 (5)	0.4153 (18)	0.3667 (4)	0.089 (3)
H5	1.3267	0.4150	0.3831	0.107*
C6	1.2101 (4)	0.2525 (16)	0.3940 (3)	0.071 (2)
H6	1.2354	0.1448	0.4289	0.085*
C7	0.9812 (4)	−0.0135 (12)	0.3804 (3)	0.0426 (16)
C8	0.9514 (3)	−0.2274 (13)	0.4215 (3)	0.0440 (16)
H8A	0.9736	−0.1789	0.4659	0.053*
H8B	0.9781	−0.4008	0.4144	0.053*
C9	0.8499 (4)	−0.2600 (12)	0.4085 (3)	0.0487 (17)
H9A	0.8356	−0.4171	0.4317	0.058*
H9B	0.8272	−0.2944	0.3634	0.058*
C10	0.8029 (4)	−0.0102 (12)	0.4276 (3)	0.0418 (16)
C11	0.6627 (4)	0.2679 (12)	0.3937 (3)	0.0399 (15)
C12	0.6588 (4)	0.3788 (13)	0.4515 (3)	0.0477 (17)
H7	0.6988	0.3221	0.4884	0.057*
C13	0.5948 (4)	0.5757 (14)	0.4546 (3)	0.0555 (18)
H13	0.5927	0.6499	0.4940	0.067*
C14	0.5343 (4)	0.6647 (12)	0.4013 (4)	0.0497 (17)
C15	0.5394 (4)	0.5532 (14)	0.3437 (3)	0.0569 (19)
H15	0.4995	0.6109	0.3068	0.068*
C16	0.6028 (4)	0.3567 (13)	0.3398 (3)	0.0513 (17)
H16	0.6051	0.2835	0.3004	0.062*
C17	0.4654 (5)	0.8807 (15)	0.4067 (4)	0.086 (3)
H17A	0.4060	0.8100	0.3904	0.103*
H17B	0.4746	1.0382	0.3824	0.103*
H17C	0.4719	0.9309	0.4505	0.103*
N1	1.0664 (3)	0.0735 (11)	0.4004 (2)	0.0475 (14)
H1N	1.095 (3)	−0.005 (11)	0.4340 (17)	0.057*
N2	0.7246 (3)	0.0584 (10)	0.3870 (2)	0.0421 (13)
H2N	0.716 (4)	−0.031 (10)	0.3519 (16)	0.051*
O1	0.9311 (3)	0.0725 (11)	0.3319 (2)	0.0762 (16)
O2	0.8342 (3)	0.1165 (8)	0.47672 (18)	0.0509 (12)
O3	0.7946 (3)	0.3120 (9)	0.2425 (2)	0.0596 (13)
H31	0.839 (3)	0.268 (11)	0.273 (2)	0.071*
H32	0.773 (4)	0.460 (8)	0.253 (3)	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.054 (4)	0.044 (4)	0.040 (4)	−0.001 (4)	0.001 (3)	−0.004 (3)
C2	0.069 (5)	0.070 (5)	0.049 (4)	0.004 (4)	0.011 (4)	0.007 (4)
C3	0.102 (7)	0.073 (6)	0.063 (5)	0.011 (6)	0.011 (5)	0.020 (5)
C4	0.100 (7)	0.078 (6)	0.084 (6)	−0.026 (6)	0.003 (5)	0.008 (5)
C5	0.071 (5)	0.099 (7)	0.088 (6)	−0.024 (5)	−0.004 (5)	0.025 (6)
C6	0.057 (5)	0.076 (6)	0.068 (5)	−0.015 (4)	−0.009 (4)	0.015 (4)
C7	0.039 (3)	0.043 (4)	0.043 (4)	0.008 (3)	0.002 (3)	−0.005 (3)
C8	0.036 (3)	0.039 (4)	0.053 (4)	0.003 (3)	0.003 (3)	−0.008 (3)
C9	0.042 (4)	0.032 (4)	0.065 (4)	−0.002 (3)	−0.004 (3)	−0.011 (3)
C10	0.036 (3)	0.040 (4)	0.044 (4)	−0.009 (3)	−0.003 (3)	0.005 (3)
C11	0.037 (3)	0.034 (4)	0.045 (4)	−0.004 (3)	0.001 (3)	−0.003 (3)
C12	0.037 (3)	0.052 (4)	0.049 (4)	0.002 (3)	−0.001 (3)	−0.001 (4)
C13	0.047 (4)	0.060 (5)	0.058 (4)	−0.001 (4)	0.009 (3)	−0.007 (4)
C14	0.036 (4)	0.031 (4)	0.083 (5)	−0.002 (3)	0.015 (4)	0.003 (4)
C15	0.041 (4)	0.054 (5)	0.067 (5)	0.009 (4)	−0.004 (3)	0.013 (4)
C16	0.046 (4)	0.054 (4)	0.047 (4)	0.003 (4)	−0.004 (3)	0.005 (3)
C17	0.072 (5)	0.071 (6)	0.113 (7)	−0.001 (5)	0.016 (5)	0.004 (5)
N1	0.043 (3)	0.052 (4)	0.040 (3)	0.002 (3)	−0.005 (2)	0.012 (3)
N2	0.036 (3)	0.043 (3)	0.041 (3)	−0.002 (3)	−0.004 (2)	−0.009 (3)
O1	0.051 (3)	0.100 (4)	0.062 (3)	0.001 (3)	−0.020 (2)	0.032 (3)
O2	0.050 (3)	0.047 (3)	0.046 (2)	0.006 (2)	−0.010 (2)	−0.005 (2)
O3	0.060 (3)	0.053 (3)	0.056 (3)	0.009 (2)	−0.008 (2)	0.005 (2)

Geometric parameters (Å, º) top

C1—C2	1.380 (8)	C10—O2	1.227 (6)
C1—C6	1.396 (8)	C10—N2	1.356 (6)
C1—N1	1.410 (8)	C11—C12	1.372 (8)
C2—C3	1.377 (10)	C11—C16	1.378 (7)
C2—H2	0.9300	C11—N2	1.424 (7)
C3—C4	1.388 (10)	C12—C13	1.385 (8)
C3—H3	0.9300	C12—H7	0.9300
C4—C5	1.370 (10)	C13—C14	1.373 (8)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.376 (9)	C14—C15	1.374 (9)
C5—H5	0.9300	C14—C17	1.515 (9)
C6—H6	0.9300	C15—C16	1.381 (8)
C7—O1	1.222 (6)	C15—H15	0.9300
C7—N1	1.343 (7)	C16—H16	0.9300
C7—C8	1.507 (8)	C17—H17A	0.9600
C8—C9	1.517 (7)	C17—H17B	0.9600
C8—H8A	0.9700	C17—H17C	0.9600
C8—H8B	0.9700	N1—H1N	0.85 (2)
C9—C10	1.522 (8)	N2—H2N	0.859 (19)
C9—H9A	0.9700	O3—H31	0.854 (19)
C9—H9B	0.9700	O3—H32	0.847 (19)

C2—C1—C6	118.8 (7)	O2—C10—C9	121.7 (5)
C2—C1—N1	124.2 (6)	N2—C10—C9	115.1 (5)
C6—C1—N1	117.0 (6)	C12—C11—C16	119.0 (6)
C3—C2—C1	119.6 (7)	C12—C11—N2	122.9 (5)
C3—C2—H2	120.2	C16—C11—N2	118.1 (5)
C1—C2—H2	120.2	C11—C12—C13	119.6 (6)
C2—C3—C4	121.7 (7)	C11—C12—H7	120.2
C2—C3—H3	119.1	C13—C12—H7	120.2
C4—C3—H3	119.1	C14—C13—C12	122.0 (6)
C5—C4—C3	118.5 (8)	C14—C13—H13	119.0
C5—C4—H4	120.8	C12—C13—H13	119.0
C3—C4—H4	120.8	C13—C14—C15	117.8 (6)
C4—C5—C6	120.6 (8)	C13—C14—C17	120.4 (7)
C4—C5—H5	119.7	C15—C14—C17	121.8 (6)
C6—C5—H5	119.7	C14—C15—C16	120.9 (6)
C5—C6—C1	120.8 (7)	C14—C15—H15	119.5
C5—C6—H6	119.6	C16—C15—H15	119.5
C1—C6—H6	119.6	C11—C16—C15	120.7 (6)
O1—C7—N1	122.6 (6)	C11—C16—H16	119.7
O1—C7—C8	122.0 (5)	C15—C16—H16	119.7
N1—C7—C8	115.4 (5)	C14—C17—H17A	109.5
C7—C8—C9	113.1 (5)	C14—C17—H17B	109.5
C7—C8—H8A	109.0	H17A—C17—H17B	109.5
C9—C8—H8A	109.0	C14—C17—H17C	109.5
C7—C8—H8B	109.0	H17A—C17—H17C	109.5
C9—C8—H8B	109.0	H17B—C17—H17C	109.5
H8A—C8—H8B	107.8	C7—N1—C1	129.4 (5)
C8—C9—C10	112.8 (5)	C7—N1—H1N	114 (4)
C8—C9—H9A	109.0	C1—N1—H1N	116 (4)
C10—C9—H9A	109.0	C10—N2—C11	128.4 (5)
C8—C9—H9B	109.0	C10—N2—H2N	113 (4)
C10—C9—H9B	109.0	C11—N2—H2N	119 (4)
H9A—C9—H9B	107.8	H31—O3—H32	107 (3)
O2—C10—N2	123.2 (6)

C6—C1—C2—C3	2.1 (10)	C12—C13—C14—C15	−0.5 (10)
N1—C1—C2—C3	−179.6 (6)	C12—C13—C14—C17	−179.9 (6)
C1—C2—C3—C4	−1.3 (12)	C13—C14—C15—C16	0.5 (10)
C2—C3—C4—C5	0.1 (13)	C17—C14—C15—C16	179.9 (6)
C3—C4—C5—C6	0.1 (13)	C12—C11—C16—C15	−0.3 (9)
C4—C5—C6—C1	0.7 (13)	N2—C11—C16—C15	177.9 (5)
C2—C1—C6—C5	−1.9 (11)	C14—C15—C16—C11	−0.1 (10)
N1—C1—C6—C5	179.7 (7)	O1—C7—N1—C1	−7.0 (10)
O1—C7—C8—C9	−16.9 (8)	C8—C7—N1—C1	172.5 (6)
N1—C7—C8—C9	163.6 (5)	C2—C1—N1—C7	16.7 (10)
C7—C8—C9—C10	−67.0 (7)	C6—C1—N1—C7	−165.0 (6)
C8—C9—C10—O2	−40.1 (8)	O2—C10—N2—C11	−4.1 (9)
C8—C9—C10—N2	140.3 (5)	C9—C10—N2—C11	175.4 (5)
C16—C11—C12—C13	0.3 (9)	C12—C11—N2—C10	−21.1 (9)
N2—C11—C12—C13	−177.9 (5)	C16—C11—N2—C10	160.7 (6)
C11—C12—C13—C14	0.1 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.85 (2)	2.06 (2)	2.895 (6)	168 (6)
N2—H2N···O3ⁱⁱ	0.86 (2)	2.15 (2)	2.992 (6)	169 (5)
O3—H31···O1	0.85 (2)	1.93 (2)	2.762 (6)	165 (5)
O3—H32···O3ⁱⁱⁱ	0.85 (2)	2.03 (2)	2.858 (5)	166 (5)

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₂·H₂O
M_r	300.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	15.242 (4), 4.905 (1), 21.540 (5)
β (°)	102.90 (2)
V (Å³)	1569.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
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	0.962, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	5068, 2805, 1356
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.117, 0.239, 1.16
No. of reflections	2805
No. of parameters	211
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)	0.35, −0.31

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···O2ⁱ	0.85 (2)	2.06 (2)	2.895 (6)	168 (6)
N2—H2N···O3ⁱⁱ	0.859 (19)	2.15 (2)	2.992 (6)	169 (5)
O3—H31···O1	0.854 (19)	1.93 (2)	2.762 (6)	165 (5)
O3—H32···O3ⁱⁱⁱ	0.847 (19)	2.03 (2)	2.858 (5)	166 (5)

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+3/2, 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 program.

References

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