organic compounds
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
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
Structure description
such as the title compound were prepared during an on-going study of the coordination chemistry of organotin carboxylates of derived from amino acids (Basu BaulThe 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.
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).
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 .
details are summarized in Table 2
|
Structural data
CCDC reference: 1443503
10.1107/S2414314615024530/vm4003sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314615024530/vm4003Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314615024530/vm4003Isup3.cml
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.
The carbon-bound H-atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and were included in the
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).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.
Reduced
such as the title compound were prepared during an on-going study of the coordination chemistry of organotin carboxylates of 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 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).
Data collection: CrysAlis PRO (Agilent, 2013); cell
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).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. |
C10H13NO3·H2O | F(000) = 456 |
Mr = 213.23 | Dx = 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 |
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 | Rint = 0.015 |
ω scans | θmax = 27.5°, θmin = 3.4° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | h = −9→4 |
Tmin = 0.971, Tmax = 1.000 | k = −22→20 |
5004 measured reflections | l = −9→11 |
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen 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 = 1.05 | Δρmax = 0.16 e Å−3 |
2344 reflections | Δρmin = −0.20 e Å−3 |
151 parameters |
C10H13NO3·H2O | V = 1059.05 (9) Å3 |
Mr = 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)° |
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 = 1.000 | Rint = 0.015 |
5004 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 151 parameters |
wR(F2) = 0.109 | 6 restraints |
S = 1.05 | Δρmax = 0.16 e Å−3 |
2344 reflections | Δρmin = −0.20 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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. |
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 |
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) |
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) |
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 (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 |
Δρmax, Δρmin (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.
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