3-[(2-Hy­droxy­benz­yl)aza­nium­yl]propano­ate monohydrate

Baul, T.S.B.; Chaurasiya, A.; Tiekink, E.R.T.

doi:10.1107/S2414314615024530

organic compounds

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ISSN: 2414-3146

Volume 1| Part 1| January 2016| x152453

doi:10.1107/S2414314615024530

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3-[(2-Hydroxybenzyl)azaniumyl]propanoate monohydrate

Tushar S. Basu Baul,^a ‡ Anurag Chaurasiya ^a and Edward R. T. Tiekink ^b ^*

^aCentre for Advanced Studies in Chemistry, North-Eastern Hill University, NEHU Permanent Campus, Umshing, Shillong 793 022, India, and ^bCentre for Crystalline Materials, Faculty of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
^*Correspondence e-mail: edwardt@sunway.edu.my

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 16 December 2015; accepted 21 December 2015; online 12 January 2016)

The title compound, C₁₀H₁₃NO₃·H₂O, is a zwitterion hydrate with the zwitterion comprising a central ammonium group and a carboxylate residue. In the zwitterion, the hydroxybenzene and carboxylate groups are directed to the same side of the molecule and each orientated to place an O atom in a position to form an intramolecular ammonium-N—H⋯O hydrogen bond, each closing an S(6) loop. The three-dimensional architecture is stabilized by hydroxy-O—H⋯O(carboxylate), water-O—H⋯O(carboxylate) and ammonium-N—H⋯O(water) hydrogen bonds.

Keywords: crystal structure; zwitterion; hydrogen bonding.

CCDC reference: 1443503

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Chemical scheme

Structure description

Reduced Schiff bases such as the title compound were prepared during an on-going study of the coordination chemistry of organotin carboxylates of Schiff bases derived from amino acids (Basu Baul et al., 2013 ).

The title compound, Fig. 1, features a 2-(OH)C₆H₄CH₂NH₂⁺CH₂CH₂CO₂⁻ zwitterion and a water molecule of crystallization. The assignment is confirmed by the equivalence of the C O bond lengths, i.e. C10—O2, O3 are 1.2527 (16) and 1.2496 (16) Å, respectively, and the pattern of hydrogen bonding involving the ammonium cation, as discussed below. The C2—C7—N1—C8—C9 backbone of the zwitterion is planar with a r.m.s. deviation = 0.0121 Å. The hydroxybenzene ring is twisted out of this plane [dihedral angle = 70.07 (8)°] as is the carboxylate group [dihedral angle = 48.26 (12)°]. The terminal residues lie approximately to the same side of the molecule and form a dihedral angle of 34.16 (15)°. The somewhat flattened U-shaped conformation places both the hydroxy-O atom and one carboxylate-O atom in proximity to one of the ammonium-N—H atoms leading to the formation of intramolecular N—H⋯O hydrogen bonds and a pair of S(6) loops, Table 1.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2N⋯O1	0.91 (1)	2.45 (1)	2.9862 (16)	118 (1)
N1—H2N⋯O2	0.91 (1)	2.02 (1)	2.7174 (15)	133 (1)
O1—H1O⋯O2ⁱ	0.85 (2)	1.83 (2)	2.6607 (16)	167 (2)
N1—H1N⋯O1Wⁱⁱ	0.92 (1)	1.83 (1)	2.7460 (15)	171 (1)
O1W—H1W⋯O3	0.85 (1)	1.89 (1)	2.7274 (15)	166 (2)
O1W—H2W⋯O3ⁱⁱⁱ	0.85 (2)	1.92 (2)	2.7710 (15)	176 (1)
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level. Hydrogen bonds are shown as dashed lines.

In the crystal, O—H⋯O and N—H⋯O hydrogen bonds, Table 1, assemble the components into a three-dimensional architecture. The water molecule participates in two donor hydrogen bonds, bridging symmetry-related carboxylate-O3 atoms along the c axis, and an acceptor, i.e. ammonium-N—H⋯O(water), hydrogen bond along the b axis. Finally, hydroxy-O—H⋯O2(carboxylate) hydrogen bonds provide links along the a axis, Fig. 2.

Figure 2
A view of the unit-cell contents of the title compound shown in projection down the c axis. The O—H⋯O and N—H⋯O hydrogen bonds are shown as orange and blue dashed lines, respectively.

The most closely related structure available in the literature is that of the 5-bromo zwitterion derivative (Yin et al., 2006 ). A different conformation is found so that while both terminal residues remain directed to one side of the planar backbone, the hydroxy group is orientated away from the central ammonium group precluding the formation of an intramolecular hydrogen bond. Finally, the title zwitterion has been reported to complex copper(I) via a carboxylate-O atom in the [Cu(⁻O₂CCH₂CH₂NH₂⁺CH₂C₆H₄OH-2)(1,10-phenanthroline)]ClO₄ salt (Yang et al., 2001 ).

Synthesis and crystallization

Salicylaldehyde (1.37 g, 11.22 mmol) in ethanol (2 ml) was added dropwise to a previously ice-cooled solution of β-alanine (1 g, 11.22 mmol) in water (6 ml) containing KOH (0.62 g, 11.22 mmol). The resulting yellow reaction mixture was allowed to stir for 2 h at room temperature and then the reaction mixture was again placed in an ice-bath. An aqueous solution of sodium borohydride (0.59 g, 15.59 mmol) in water (2 ml) was added dropwise with stirring to the cooled solution. The yellow colour slowly discharged and stirring continued for another 3 h. The reaction mixture was then acidified with dilute acetic acid to maintain a pH of 5. The resulting colourless solid was filtered off, washed successively with water, ethanol and diethyl ether, and dried in vacuo. The dried product was recrystallized from a water/ethanol (1:1) mixture. Yield: 70%. M.p. 128–130°C. Crystals were grown from an aqueous solution of the compound by slow evaporation at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO₃·H₂O
M_r	213.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.3280 (4), 17.0138 (7), 8.9223 (4)
β (°)	107.818 (5)
V (Å³)	1059.05 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Agilent Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2013 )
T_min, T_max	0.971, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5004, 2344, 1962
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.05
No. of reflections	2344
No. of parameters	151
No. of restraints	6
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20
Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), DIAMOND (Brandenburg, 2006 ), publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1443503

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314615024530/vm4003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314615024530/vm4003Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314615024530/vm4003Isup3.cml

checkCIF report

Synthesis and crystallization top

Salicylaldehyde (1.37 g, 11.22 mmol) in ethanol (2 ml) was added drop-wise to a previously ice-cooled solution of β-alanine (1 g, 11.22 mmol) in water (6 ml) containing KOH (0.62 g, 11.22 mmol). The resulting yellow reaction mixture was allowed to stir for 2 h at room temperature and then the reaction mixture was again placed in an ice-bath. An aqueous solution of sodium borohydride (0.59 g 15.59 mmol) in water (2 ml) was added drop-wise with stirring to the cooled solution. The yellow colour slowly discharged and stirring continued for another 3 h. The reaction mixture was then acidified with dilute acetic acid to maintain a pH of 5. The resulting colourless solid was filtered off, washed successively with water, ethanol and diethyl ether, and dried in vacuo. The dried product was recrystallized from a water/ethanol (1:1) mixture. Yield: 70%. M.pt: 128-130 °C. Crystals were grown from an aqueous solution of the compound by slow evaporation at room temperature.

Refinement top

The carbon-bound H-atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U_iso(H) set to 1.2–1.5U_equiv(C). The oxygen- and nitrogen-bound H-atoms were located in a difference Fourier map but were refined with a distance restraints of O—H = 0.84±0.01 Å and N—H = 0.91±0.01 Å, and with U_iso(H) = 1.5U_equiv(O) or 1.2U_equiv(N).

Experimental top

Salicylaldehyde (1.37 g, 11.22 mmol) in ethanol (2 ml) was added drop-wise to a previously ice-cooled solution of β-alanine (1 g, 11.22 mmol) in water (6 ml) containing KOH (0.62 g, 11.22 mmol). The resulting yellow reaction mixture was allowed to stir for 2 h at room temperature and then the reaction mixture was again placed in an ice-bath. An aqueous solution of sodium borohydride (0.59 g, 15.59 mmol) in water (2 ml) was added drop-wise with stirring to the cooled solution. The yellow colour slowly discharged and stirring continued for another 3 h. The reaction mixture was then acidified with dilute acetic acid to maintain a pH of 5. The resulting colourless solid was filtered off, washed successively with water, ethanol and diethyl ether, and dried in vacuo. The dried product was recrystallized from a water/ethanol (1:1) mixture. Yield: 70%. M.p. 128–130°C. Crystals were grown from an aqueous solution of the compound by slow evaporation at room temperature.

Structure description top

The title compound, Fig. 1, features a 2-(OH)C₆H₄CH₂NH₂⁺CH₂CH₂CO₂^- zwitterion and a water molecule of crystallization. The assignment is confirmed by the equivalence of the C≐O bond lengths, i.e. C10—O2, O3 are 1.2527 (16) and 1.2496 (16) Å, respectively, and the pattern of hydrogen bonding involving the ammonium cation, as discussed below. The C2—C7—N1—C8—C9 backbone of the zwitterion is planar with a r.m.s. deviation = 0.0121 Å. The hydroxybenzene ring is twisted out of this plane [dihedral angle = 70.07 (8)°] as is the carboxylate group [dihedral angle = 48.26 (12)°]. The terminal residues lies approximately to the same side of the molecule and form a dihedral angle of 34.16 (15)°. The somewhat flattened U-shaped conformation places both the hydroxy-O atom and one carboxylate-O atom in proximity to one of the ammonium-N—H atoms leading to the formation of intramolecular N—H···O hydrogen bonds and a pair of S(6) loops, Table 1.

In the crystal, O—H···O and N—H···O hydrogen bonds, Table 1, assemble the components into a three-dimensional architecture. The water molecule participates in two donor hydrogen bonds, bridging symmetry-related carboxylate-O3 atoms along the c axis, and an acceptor, i.e. ammonium-N—H···O(water), hydrogen bond along the b axis. Finally, hydroxy-O—H···O2(carboxylate) hydrogen bonds provide links along the a axis, Fig. 2.

The most closely related structure available in the literature is that of the 5-bromo zwitterion derivative (Yin et al., 2006). A different conformation is found so that while both terminal residues remain directed to one side of the planar backbone, the hydroxy group is orientated away from the central ammonium group precluding the formation of an intramolecular hydrogen bond. Finally, the title zwitterion has been reported to complex copper(I) via a carboxylate-O atom in the [Cu(^–O₂CCH₂CH₂NH₂⁺CH₂C₆H₄OH-2)(1,10-phenanthroline)]ClO₄ salt (Yang et al., 2001).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A view of the unit-cell contents of the title compound shown in projection down the c axis. The O—H···O and N—H···O hydrogen bonds are shown as orange and blue dashed lines, respectively.

3-[(2-Hydroxybenzyl)azaniumyl]propanoate monohydrate top

Crystal data top

C₁₀H₁₃NO₃·H₂O	F(000) = 456
M_r = 213.23	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.3280 (4) Å	Cell parameters from 1703 reflections
b = 17.0138 (7) Å	θ = 3.8–28.6°
c = 8.9223 (4) Å	µ = 0.10 mm⁻¹
β = 107.818 (5)°	T = 293 K
V = 1059.05 (9) Å³	Prism, colourless
Z = 4	0.35 × 0.25 × 0.15 mm

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	2344 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1962 reflections with I > 2σ(I)
Detector resolution: 16.1279 pixels mm^-1	R_int = 0.015
ω scans	θ_max = 27.5°, θ_min = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	h = −9→4
T_min = 0.971, T_max = 1.000	k = −22→20
5004 measured reflections	l = −9→11

Refinement top

Refinement on F²	6 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	w = 1/[σ²(F_o²) + (0.052P)² + 0.2051P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.109	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.16 e Å⁻³
2344 reflections	Δρ_min = −0.20 e Å⁻³
151 parameters

Crystal data top

C₁₀H₁₃NO₃·H₂O	V = 1059.05 (9) Å³
M_r = 213.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3280 (4) Å	µ = 0.10 mm⁻¹
b = 17.0138 (7) Å	T = 293 K
c = 8.9223 (4) Å	0.35 × 0.25 × 0.15 mm
β = 107.818 (5)°

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	2344 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	1962 reflections with I > 2σ(I)
T_min = 0.971, T_max = 1.000	R_int = 0.015
5004 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	151 parameters
wR(F²) = 0.109	6 restraints
S = 1.05	Δρ_max = 0.16 e Å⁻³
2344 reflections	Δρ_min = −0.20 e Å⁻³

Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.76143 (15)	0.52616 (7)	0.81882 (14)	0.0502 (3)
H1O	0.805 (3)	0.5632 (9)	0.884 (2)	0.075*
O2	1.05270 (14)	0.35918 (6)	0.99304 (12)	0.0456 (3)
O3	1.26960 (15)	0.26454 (7)	1.02418 (12)	0.0486 (3)
N1	0.72736 (16)	0.35468 (6)	0.74403 (12)	0.0314 (3)
H1N	0.6506 (18)	0.3222 (8)	0.7816 (17)	0.038*
H2N	0.8050 (19)	0.3831 (8)	0.8240 (14)	0.038*
C1	0.56867 (19)	0.51930 (8)	0.78695 (16)	0.0354 (3)
C2	0.48179 (19)	0.45826 (7)	0.68570 (15)	0.0348 (3)
C3	0.2865 (2)	0.44795 (9)	0.6492 (2)	0.0487 (4)
H3	0.2273	0.4075	0.5817	0.058*
C4	0.1777 (2)	0.49673 (10)	0.7112 (2)	0.0564 (4)
H4	0.0458	0.4896	0.6848	0.068*
C5	0.2656 (2)	0.55610 (9)	0.8125 (2)	0.0499 (4)
H5	0.1926	0.5886	0.8555	0.060*
C6	0.4608 (2)	0.56783 (8)	0.85086 (18)	0.0428 (3)
H6	0.5193	0.6081	0.9192	0.051*
C7	0.6016 (2)	0.40636 (8)	0.61911 (15)	0.0376 (3)
H7A	0.6803	0.4384	0.5734	0.045*
H7B	0.5190	0.3741	0.5362	0.045*
C8	0.85599 (19)	0.30361 (9)	0.68568 (15)	0.0371 (3)
H8A	0.9369	0.3363	0.6434	0.045*
H8B	0.7790	0.2708	0.6010	0.045*
C9	0.9807 (2)	0.25196 (8)	0.81421 (16)	0.0360 (3)
H9A	1.0585	0.2190	0.7692	0.043*
H9B	0.8985	0.2176	0.8519	0.043*
C10	1.11237 (19)	0.29581 (8)	0.95388 (14)	0.0338 (3)
O1W	1.49712 (14)	0.25271 (6)	1.32892 (12)	0.0436 (3)
H2W	1.424 (2)	0.2457 (11)	1.3856 (19)	0.065*
H1W	1.424 (2)	0.2644 (11)	1.2376 (13)	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0322 (6)	0.0544 (6)	0.0607 (7)	−0.0073 (5)	0.0095 (5)	−0.0260 (5)
O2	0.0373 (5)	0.0473 (6)	0.0457 (6)	0.0019 (5)	0.0029 (4)	−0.0185 (5)
O3	0.0423 (6)	0.0615 (7)	0.0355 (5)	0.0138 (5)	0.0021 (4)	−0.0033 (5)
N1	0.0301 (6)	0.0357 (6)	0.0259 (5)	−0.0023 (5)	0.0048 (4)	−0.0023 (4)
C1	0.0318 (7)	0.0359 (7)	0.0357 (7)	−0.0005 (6)	0.0060 (5)	0.0029 (5)
C2	0.0335 (7)	0.0323 (6)	0.0345 (6)	−0.0002 (5)	0.0044 (5)	0.0056 (5)
C3	0.0375 (8)	0.0439 (8)	0.0574 (9)	−0.0081 (7)	0.0039 (7)	0.0035 (7)
C4	0.0318 (8)	0.0585 (10)	0.0771 (12)	−0.0009 (7)	0.0140 (8)	0.0110 (9)
C5	0.0454 (9)	0.0471 (8)	0.0621 (10)	0.0136 (7)	0.0238 (8)	0.0138 (7)
C6	0.0447 (8)	0.0371 (7)	0.0465 (8)	0.0030 (6)	0.0139 (7)	0.0006 (6)
C7	0.0417 (8)	0.0372 (7)	0.0275 (6)	−0.0015 (6)	0.0013 (5)	0.0000 (5)
C8	0.0357 (7)	0.0475 (8)	0.0279 (6)	−0.0004 (6)	0.0094 (5)	−0.0070 (5)
C9	0.0354 (7)	0.0377 (7)	0.0348 (7)	0.0020 (6)	0.0105 (6)	−0.0081 (5)
C10	0.0319 (7)	0.0426 (7)	0.0275 (6)	−0.0005 (6)	0.0096 (5)	−0.0017 (5)
O1W	0.0345 (5)	0.0573 (6)	0.0369 (5)	0.0042 (5)	0.0079 (4)	−0.0007 (5)

Geometric parameters (Å, º) top

O1—C1	1.3579 (17)	C4—H4	0.9300
O1—H1O	0.849 (9)	C5—C6	1.380 (2)
O2—C10	1.2527 (16)	C5—H5	0.9300
O3—C10	1.2496 (16)	C6—H6	0.9300
N1—C8	1.4882 (17)	C7—H7A	0.9700
N1—C7	1.4955 (16)	C7—H7B	0.9700
N1—H1N	0.922 (9)	C8—C9	1.5104 (19)
N1—H2N	0.904 (9)	C8—H8A	0.9700
C1—C6	1.381 (2)	C8—H8B	0.9700
C1—C2	1.3956 (19)	C9—C10	1.5180 (18)
C2—C3	1.378 (2)	C9—H9A	0.9700
C2—C7	1.491 (2)	C9—H9B	0.9700
C3—C4	1.379 (2)	O1W—H2W	0.850 (9)
C3—H3	0.9300	O1W—H1W	0.851 (9)
C4—C5	1.377 (3)

C1—O1—H1O	110.9 (14)	C1—C6—H6	120.3
C8—N1—C7	113.24 (10)	C2—C7—N1	110.80 (10)
C8—N1—H1N	107.4 (9)	C2—C7—H7A	109.5
C7—N1—H1N	108.5 (9)	N1—C7—H7A	109.5
C8—N1—H2N	106.0 (10)	C2—C7—H7B	109.5
C7—N1—H2N	111.7 (9)	N1—C7—H7B	109.5
H1N—N1—H2N	109.9 (13)	H7A—C7—H7B	108.1
O1—C1—C6	123.51 (13)	N1—C8—C9	112.02 (10)
O1—C1—C2	116.03 (12)	N1—C8—H8A	109.2
C6—C1—C2	120.45 (13)	C9—C8—H8A	109.2
C3—C2—C1	118.87 (14)	N1—C8—H8B	109.2
C3—C2—C7	121.71 (13)	C9—C8—H8B	109.2
C1—C2—C7	119.42 (12)	H8A—C8—H8B	107.9
C2—C3—C4	120.98 (15)	C8—C9—C10	114.98 (11)
C2—C3—H3	119.5	C8—C9—H9A	108.5
C4—C3—H3	119.5	C10—C9—H9A	108.5
C5—C4—C3	119.54 (15)	C8—C9—H9B	108.5
C5—C4—H4	120.2	C10—C9—H9B	108.5
C3—C4—H4	120.2	H9A—C9—H9B	107.5
C4—C5—C6	120.70 (15)	O3—C10—O2	124.98 (12)
C4—C5—H5	119.7	O3—C10—C9	117.36 (12)
C6—C5—H5	119.7	O2—C10—C9	117.62 (11)
C5—C6—C1	119.46 (14)	H2W—O1W—H1W	106.0 (15)
C5—C6—H6	120.3

O1—C1—C2—C3	179.74 (13)	O1—C1—C6—C5	−179.56 (14)
C6—C1—C2—C3	0.8 (2)	C2—C1—C6—C5	−0.7 (2)
O1—C1—C2—C7	−0.67 (18)	C3—C2—C7—N1	−110.11 (14)
C6—C1—C2—C7	−179.59 (12)	C1—C2—C7—N1	70.31 (16)
C1—C2—C3—C4	−0.1 (2)	C8—N1—C7—C2	−177.77 (11)
C7—C2—C3—C4	−179.67 (14)	C7—N1—C8—C9	−179.82 (11)
C2—C3—C4—C5	−0.7 (3)	N1—C8—C9—C10	−59.93 (15)
C3—C4—C5—C6	0.8 (2)	C8—C9—C10—O3	−148.37 (13)
C4—C5—C6—C1	−0.1 (2)	C8—C9—C10—O2	33.91 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N···O1	0.91 (1)	2.45 (1)	2.9862 (16)	118 (1)
N1—H2N···O2	0.91 (1)	2.02 (1)	2.7174 (15)	133 (1)
O1—H1O···O2ⁱ	0.85 (2)	1.83 (2)	2.6607 (16)	167 (2)
N1—H1N···O1Wⁱⁱ	0.92 (1)	1.83 (1)	2.7460 (15)	171 (1)
O1W—H1W···O3	0.85 (1)	1.89 (1)	2.7274 (15)	166 (2)
O1W—H2W···O3ⁱⁱⁱ	0.85 (2)	1.92 (2)	2.7710 (15)	176 (1)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N···O1	0.905 (13)	2.453 (14)	2.9862 (16)	118.0 (10)
N1—H2N···O2	0.905 (13)	2.015 (13)	2.7174 (15)	133.4 (12)
O1—H1O···O2ⁱ	0.851 (17)	1.826 (17)	2.6607 (16)	167 (2)
N1—H1N···O1Wⁱⁱ	0.922 (14)	1.833 (14)	2.7460 (15)	170.6 (13)
O1W—H1W···O3	0.851 (12)	1.894 (12)	2.7274 (15)	166.1 (18)
O1W—H2W···O3ⁱⁱⁱ	0.850 (16)	1.922 (16)	2.7710 (15)	175.8 (14)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO₃·H₂O
M_r	213.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.3280 (4), 17.0138 (7), 8.9223 (4)
β (°)	107.818 (5)
V (Å³)	1059.05 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Agilent Xcalibur Eos Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2013)
T_min, T_max	0.971, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5004, 2344, 1962
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.05
No. of reflections	2344
No. of parameters	151
No. of restraints	6
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20

Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Footnotes

‡Additonal correspondence author, e-mail: basubaulchem@gmail.com.

Acknowledgements

The financial support from the Council of Scientific and Industrial Research, New Delhi [grant No. 01 (2734)/13/ EMR-II, 2013; TSBB] and the Department of Biotechnology, New Delhi (grant No. BT/329/NE/TBP/2012; TSBB, AC) are gratefully acknowledged. TSBB and AC also acknowledge DST–PURSE for the X-ray diffractometer facility.

References

Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA. Google Scholar
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ISSN: 2414-3146

Volume 1| Part 1| January 2016| x152453

doi:10.1107/S2414314615024530

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