organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

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

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

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[Basu Baul, T. S., Kehie, P., Chanu, O. B., Duthie, A. & Höpfl, H. (2013). J. Organomet. Chem. 733, 36-43.]).

The title compound, Fig. 1[link], 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[link].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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]
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[link], 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[link].

[Figure 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[Yin, X.-J., Cai, J.-H. & Ng, S. W. (2006). Acta Cryst. E62, o5409-o5410.]). 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[Yang, C. T., Moubaraki, B., Murray, K. S., Ranford, J. D. & Vittal, J. J. (2001). Inorg. Chem. 40, 5934-5941.]).

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[link].

Table 2
Experimental details

Crystal data
Chemical formula C10H13NO3·H2O
Mr 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)
V3) 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[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.])
Tmin, Tmax 0.971, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 5004, 2344, 1962
Rint 0.015
(sin θ/λ)max−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
Δρmax, Δρmin (e Å−3) 0.16, −0.20
Computer programs: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]), publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


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 Uiso(H) set to 1.2–1.5Uequiv(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 Uiso(H) = 1.5Uequiv(O) or 1.2Uequiv(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.

Refinement top

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

Structure description top

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 CO 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
[Figure 1] 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.
[Figure 2] 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·H2OF(000) = 456
Mr = 213.23Dx = 1.337 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.3280 (4) ÅCell parameters from 1703 reflections
b = 17.0138 (7) Åθ = 3.8–28.6°
c = 8.9223 (4) ŵ = 0.10 mm1
β = 107.818 (5)°T = 293 K
V = 1059.05 (9) Å3Prism, colourless
Z = 40.35 × 0.25 × 0.15 mm
Data collection top
Agilent Xcalibur Eos Gemini
diffractometer
2344 independent reflections
Radiation source: Enhance (Mo) X-ray Source1962 reflections with I > 2σ(I)
Detector resolution: 16.1279 pixels mm-1Rint = 0.015
ω scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
h = 94
Tmin = 0.971, Tmax = 1.000k = 2220
5004 measured reflectionsl = 911
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.052P)2 + 0.2051P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.16 e Å3
2344 reflectionsΔρmin = 0.20 e Å3
151 parameters
Crystal data top
C10H13NO3·H2OV = 1059.05 (9) Å3
Mr = 213.23Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.3280 (4) ŵ = 0.10 mm1
b = 17.0138 (7) ÅT = 293 K
c = 8.9223 (4) Å0.35 × 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)
Tmin = 0.971, Tmax = 1.000Rint = 0.015
5004 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041151 parameters
wR(F2) = 0.1096 restraints
S = 1.05Δρmax = 0.16 e Å3
2344 reflectionsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
O10.76143 (15)0.52616 (7)0.81882 (14)0.0502 (3)
H1O0.805 (3)0.5632 (9)0.884 (2)0.075*
O21.05270 (14)0.35918 (6)0.99304 (12)0.0456 (3)
O31.26960 (15)0.26454 (7)1.02418 (12)0.0486 (3)
N10.72736 (16)0.35468 (6)0.74403 (12)0.0314 (3)
H1N0.6506 (18)0.3222 (8)0.7816 (17)0.038*
H2N0.8050 (19)0.3831 (8)0.8240 (14)0.038*
C10.56867 (19)0.51930 (8)0.78695 (16)0.0354 (3)
C20.48179 (19)0.45826 (7)0.68570 (15)0.0348 (3)
C30.2865 (2)0.44795 (9)0.6492 (2)0.0487 (4)
H30.22730.40750.58170.058*
C40.1777 (2)0.49673 (10)0.7112 (2)0.0564 (4)
H40.04580.48960.68480.068*
C50.2656 (2)0.55610 (9)0.8125 (2)0.0499 (4)
H50.19260.58860.85550.060*
C60.4608 (2)0.56783 (8)0.85086 (18)0.0428 (3)
H60.51930.60810.91920.051*
C70.6016 (2)0.40636 (8)0.61911 (15)0.0376 (3)
H7A0.68030.43840.57340.045*
H7B0.51900.37410.53620.045*
C80.85599 (19)0.30361 (9)0.68568 (15)0.0371 (3)
H8A0.93690.33630.64340.045*
H8B0.77900.27080.60100.045*
C90.9807 (2)0.25196 (8)0.81421 (16)0.0360 (3)
H9A1.05850.21900.76920.043*
H9B0.89850.21760.85190.043*
C101.11237 (19)0.29581 (8)0.95388 (14)0.0338 (3)
O1W1.49712 (14)0.25271 (6)1.32892 (12)0.0436 (3)
H2W1.424 (2)0.2457 (11)1.3856 (19)0.065*
H1W1.424 (2)0.2644 (11)1.2376 (13)0.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0322 (6)0.0544 (6)0.0607 (7)0.0073 (5)0.0095 (5)0.0260 (5)
O20.0373 (5)0.0473 (6)0.0457 (6)0.0019 (5)0.0029 (4)0.0185 (5)
O30.0423 (6)0.0615 (7)0.0355 (5)0.0138 (5)0.0021 (4)0.0033 (5)
N10.0301 (6)0.0357 (6)0.0259 (5)0.0023 (5)0.0048 (4)0.0023 (4)
C10.0318 (7)0.0359 (7)0.0357 (7)0.0005 (6)0.0060 (5)0.0029 (5)
C20.0335 (7)0.0323 (6)0.0345 (6)0.0002 (5)0.0044 (5)0.0056 (5)
C30.0375 (8)0.0439 (8)0.0574 (9)0.0081 (7)0.0039 (7)0.0035 (7)
C40.0318 (8)0.0585 (10)0.0771 (12)0.0009 (7)0.0140 (8)0.0110 (9)
C50.0454 (9)0.0471 (8)0.0621 (10)0.0136 (7)0.0238 (8)0.0138 (7)
C60.0447 (8)0.0371 (7)0.0465 (8)0.0030 (6)0.0139 (7)0.0006 (6)
C70.0417 (8)0.0372 (7)0.0275 (6)0.0015 (6)0.0013 (5)0.0000 (5)
C80.0357 (7)0.0475 (8)0.0279 (6)0.0004 (6)0.0094 (5)0.0070 (5)
C90.0354 (7)0.0377 (7)0.0348 (7)0.0020 (6)0.0105 (6)0.0081 (5)
C100.0319 (7)0.0426 (7)0.0275 (6)0.0005 (6)0.0096 (5)0.0017 (5)
O1W0.0345 (5)0.0573 (6)0.0369 (5)0.0042 (5)0.0079 (4)0.0007 (5)
Geometric parameters (Å, º) top
O1—C11.3579 (17)C4—H40.9300
O1—H1O0.849 (9)C5—C61.380 (2)
O2—C101.2527 (16)C5—H50.9300
O3—C101.2496 (16)C6—H60.9300
N1—C81.4882 (17)C7—H7A0.9700
N1—C71.4955 (16)C7—H7B0.9700
N1—H1N0.922 (9)C8—C91.5104 (19)
N1—H2N0.904 (9)C8—H8A0.9700
C1—C61.381 (2)C8—H8B0.9700
C1—C21.3956 (19)C9—C101.5180 (18)
C2—C31.378 (2)C9—H9A0.9700
C2—C71.491 (2)C9—H9B0.9700
C3—C41.379 (2)O1W—H2W0.850 (9)
C3—H30.9300O1W—H1W0.851 (9)
C4—C51.377 (3)
C1—O1—H1O110.9 (14)C1—C6—H6120.3
C8—N1—C7113.24 (10)C2—C7—N1110.80 (10)
C8—N1—H1N107.4 (9)C2—C7—H7A109.5
C7—N1—H1N108.5 (9)N1—C7—H7A109.5
C8—N1—H2N106.0 (10)C2—C7—H7B109.5
C7—N1—H2N111.7 (9)N1—C7—H7B109.5
H1N—N1—H2N109.9 (13)H7A—C7—H7B108.1
O1—C1—C6123.51 (13)N1—C8—C9112.02 (10)
O1—C1—C2116.03 (12)N1—C8—H8A109.2
C6—C1—C2120.45 (13)C9—C8—H8A109.2
C3—C2—C1118.87 (14)N1—C8—H8B109.2
C3—C2—C7121.71 (13)C9—C8—H8B109.2
C1—C2—C7119.42 (12)H8A—C8—H8B107.9
C2—C3—C4120.98 (15)C8—C9—C10114.98 (11)
C2—C3—H3119.5C8—C9—H9A108.5
C4—C3—H3119.5C10—C9—H9A108.5
C5—C4—C3119.54 (15)C8—C9—H9B108.5
C5—C4—H4120.2C10—C9—H9B108.5
C3—C4—H4120.2H9A—C9—H9B107.5
C4—C5—C6120.70 (15)O3—C10—O2124.98 (12)
C4—C5—H5119.7O3—C10—C9117.36 (12)
C6—C5—H5119.7O2—C10—C9117.62 (11)
C5—C6—C1119.46 (14)H2W—O1W—H1W106.0 (15)
C5—C6—H6120.3
O1—C1—C2—C3179.74 (13)O1—C1—C6—C5179.56 (14)
C6—C1—C2—C30.8 (2)C2—C1—C6—C50.7 (2)
O1—C1—C2—C70.67 (18)C3—C2—C7—N1110.11 (14)
C6—C1—C2—C7179.59 (12)C1—C2—C7—N170.31 (16)
C1—C2—C3—C40.1 (2)C8—N1—C7—C2177.77 (11)
C7—C2—C3—C4179.67 (14)C7—N1—C8—C9179.82 (11)
C2—C3—C4—C50.7 (3)N1—C8—C9—C1059.93 (15)
C3—C4—C5—C60.8 (2)C8—C9—C10—O3148.37 (13)
C4—C5—C6—C10.1 (2)C8—C9—C10—O233.91 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H2N···O10.91 (1)2.45 (1)2.9862 (16)118 (1)
N1—H2N···O20.91 (1)2.02 (1)2.7174 (15)133 (1)
O1—H1O···O2i0.85 (2)1.83 (2)2.6607 (16)167 (2)
N1—H1N···O1Wii0.92 (1)1.83 (1)2.7460 (15)171 (1)
O1W—H1W···O30.85 (1)1.89 (1)2.7274 (15)166 (2)
O1W—H2W···O3iii0.85 (2)1.92 (2)2.7710 (15)176 (1)
Symmetry codes: (i) x+2, y+1, z+2; (ii) x1, y+1/2, z1/2; (iii) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H2N···O10.905 (13)2.453 (14)2.9862 (16)118.0 (10)
N1—H2N···O20.905 (13)2.015 (13)2.7174 (15)133.4 (12)
O1—H1O···O2i0.851 (17)1.826 (17)2.6607 (16)167 (2)
N1—H1N···O1Wii0.922 (14)1.833 (14)2.7460 (15)170.6 (13)
O1W—H1W···O30.851 (12)1.894 (12)2.7274 (15)166.1 (18)
O1W—H2W···O3iii0.850 (16)1.922 (16)2.7710 (15)175.8 (14)
Symmetry codes: (i) x+2, y+1, z+2; (ii) x1, y+1/2, z1/2; (iii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC10H13NO3·H2O
Mr213.23
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.3280 (4), 17.0138 (7), 8.9223 (4)
β (°) 107.818 (5)
V3)1059.05 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.35 × 0.25 × 0.15
Data collection
DiffractometerAgilent Xcalibur Eos Gemini
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2013)
Tmin, Tmax0.971, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
5004, 2344, 1962
Rint0.015
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.109, 1.05
No. of reflections2344
No. of parameters151
No. of restraints6
Δρmax, Δρmin (e Å3)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

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