(E)-4-Amino-N′-(5-bromo-2-hy­droxy­benzyl­idene)benzohydrazide mono­hydrate

Kargar, H.; Kia, R.; Tahir, M.N.

doi:10.1107/S1600536812025950

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2120

https://doi.org/10.1107/S1600536812025950

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(E)-4-Amino-N′-(5-bromo-2-hydroxybenzylidene)benzohydrazide monohydrate

Hadi Kargar,^a ^* Reza Kia ^b ‡ and Muhammad Nawaz Tahir ^c ^*

^aDepartment of Chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, I. R. of IRAN, ^bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^cDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: h.kargar@pnu.ac.ir, dmntahir_uos@yahoo.com

(Received 3 June 2012; accepted 7 June 2012; online 16 June 2012)

In t the title compound, C₁₄H₁₂BrN₃O₂. H₂O, the conformation of the C=N double bond in the hydrazide Schiff base molecule is E. The dihedral angle between the benzene rings is 48.01 (11) °. An intramolecular O—H⋯N hydrogen bond makes an S(6) ring motif. In the crystal, molecules are linked through N—H⋯O (bifurcated acceptor) and O—H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to (100).

Related literature

For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006 ); Karthikeyan et al. (2006 ). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012 ); Shi & Li (2012 ); Bakir & Green (2002 ). For standard bond lengths, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₂BrN₃O₂·H₂O
M_r = 352.19
Monoclinic, P 2₁ /c
a = 15.8435 (11) Å
b = 7.1718 (6) Å
c = 12.6462 (8) Å
β = 101.391 (3)°
V = 1408.64 (18) Å³
Z = 4
Mo Kα radiation
μ = 2.93 mm⁻¹
T = 291 K
0.32 × 0.26 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.454, T_max = 0.565
11798 measured reflections
3138 independent reflections
2543 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.077
S = 1.04
3138 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N3	0.93	1.84	2.660 (2)	145
N2—H2N⋯O1Wⁱ	0.90	1.93	2.823 (2)	171
N1—H2N1⋯O1Wⁱⁱ	0.89	2.57	3.276 (3)	137
O1W—H2W1⋯O1	0.90	1.77	2.653 (2)	167
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812025950/su2450sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025950/su2450Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025950/su2450Isup3.cml

checkCIF report

Comment top

Schiff bases are one of the most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of coordination chemistry related to catalysis and magnetism, and supramolecular architectures (Karthikeyan et al., 2006; Kucukguzel et al., 2006). Structures of Schiff bases derived from substituted 4-aminobenzohydrazide have been reported earlier (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002). In order to explore the structure of the new Schiff base derivatives, the title compound was prepared and characterized crystallographically.

The asymmetric unit of the title compound, Fig. 1, comprises a molecule of the title hydrazide Schiff base and a water molecule of crystallization. The hydrazide Schiff base shows an E conformation around the C═N double bond. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those reported for related structures (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002). An intramolecular O—H···N hydrogen bond makes an S(6) ring motif (Table 1; Bernstein et al., 1995). The dihedral angle between the benzene rings is 48.01 (11)Å.

In the crystal, molecules are linked through N—H···O [bifurcated acceptor] and O—H···O hydrogen bonds forming two-dimensional networks lying parallel to (100) [Table 1 and Fig. 2].

Related literature top

For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006); Karthikeyan et al. (2006). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012); Shi & Li (2012); Bakir & Green (2002). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized by adding 1 mmol of methyl 4-aminobenzoate to a solution of 5-Bromosalicylaldehyde (1 mmol) in methanol (30 ml). The mixture was refluxed with stirring for 50 min and after cooling to room temperature a light-yellow precipitate was filtered and washed with diethylether and dried in air. Light-yellow prismatic crystals of the title compound, suitable for X-ray structure analysis, were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Structure description top

In the crystal, molecules are linked through N—H···O [bifurcated acceptor] and O—H···O hydrogen bonds forming two-dimensional networks lying parallel to (100) [Table 1 and Fig. 2].

For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006); Karthikeyan et al. (2006). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012); Shi & Li (2012); Bakir & Green (2002). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atom numbering. The dashed lines show the intramolecular N-H···O hydrogen bonds (see Table 1 for details).
	Fig. 2. A view along the b axis of crystal packing of the title compound, showing the linking of molecules through N—H···O and O—H···O hydrogen bonds (dashed lines; see Table 1 for details; only the NH H atom is shown).

(E)-4-Amino-N'-(5-bromo-2-hydroxybenzylidene)benzohydrazide monohydrate top

Crystal data top

C₁₄H₁₂BrN₃O₂·H₂O	F(000) = 712
M_r = 352.19	D_x = 1.661 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2225 reflections
a = 15.8435 (11) Å	θ = 2.5–27.5°
b = 7.1718 (6) Å	µ = 2.93 mm⁻¹
c = 12.6462 (8) Å	T = 291 K
β = 101.391 (3)°	Prism, white
V = 1408.64 (18) Å³	0.32 × 0.26 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3138 independent reflections
Radiation source: fine-focus sealed tube	2543 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
φ and ω scans	θ_max = 27.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −20→20
T_min = 0.454, T_max = 0.565	k = −9→8
11798 measured reflections	l = −9→16

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0361P)² + 0.4505P] where P = (F_o² + 2F_c²)/3
3138 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₄H₁₂BrN₃O₂·H₂O	V = 1408.64 (18) Å³
M_r = 352.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.8435 (11) Å	µ = 2.93 mm⁻¹
b = 7.1718 (6) Å	T = 291 K
c = 12.6462 (8) Å	0.32 × 0.26 × 0.22 mm
β = 101.391 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3138 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2543 reflections with I > 2σ(I)
T_min = 0.454, T_max = 0.565	R_int = 0.031
11798 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.04	Δρ_max = 0.27 e Å⁻³
3138 reflections	Δρ_min = −0.49 e Å⁻³
190 parameters

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.

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 > 2sigma(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
Br1	−0.256908 (14)	0.19559 (3)	0.351278 (19)	0.04528 (10)
O1	0.27754 (10)	0.3064 (2)	0.77430 (12)	0.0463 (4)
O2	0.02746 (10)	0.1315 (3)	0.74256 (12)	0.0490 (4)
H2O	0.0786	0.1768	0.7273	0.073*
O1W	0.20712 (12)	0.0602 (3)	0.88744 (12)	0.0555 (5)
H1W1	0.1801	−0.0294	0.8452	0.083*
H2W1	0.2246	0.1388	0.8402	0.083*
N1	0.61249 (13)	0.3236 (4)	0.5692 (2)	0.0675 (7)
H1N1	0.6101	0.3120	0.4985	0.081*
H2N1	0.6429	0.4174	0.6041	0.081*
N2	0.21269 (10)	0.3032 (2)	0.59806 (14)	0.0322 (4)
H2N	0.2133	0.3342	0.5294	0.039*
N3	0.13313 (11)	0.2630 (2)	0.62093 (15)	0.0321 (4)
C1	0.36621 (12)	0.3254 (3)	0.64417 (16)	0.0297 (4)
C2	0.38195 (13)	0.2378 (3)	0.55174 (17)	0.0344 (5)
H2	0.3372	0.1774	0.5059	0.041*
C3	0.46277 (15)	0.2394 (3)	0.5272 (2)	0.0425 (5)
H3	0.4721	0.1783	0.4657	0.051*
C4	0.53040 (14)	0.3309 (3)	0.5931 (2)	0.0428 (6)
C5	0.51473 (13)	0.4213 (4)	0.6841 (2)	0.0475 (6)
H5	0.5592	0.4855	0.7283	0.057*
C6	0.43430 (13)	0.4174 (3)	0.70993 (17)	0.0384 (5)
H6	0.4254	0.4771	0.7721	0.046*
C7	0.28256 (13)	0.3116 (3)	0.67866 (16)	0.0304 (4)
C8	0.06943 (13)	0.2690 (3)	0.54186 (17)	0.0321 (4)
H7	0.0781	0.3071	0.4745	0.039*
C9	−0.01679 (12)	0.2173 (3)	0.55511 (16)	0.0284 (4)
C10	−0.03425 (13)	0.1483 (3)	0.65254 (17)	0.0328 (4)
C11	−0.11712 (13)	0.0932 (3)	0.65825 (17)	0.0369 (5)
H11	−0.1282	0.0459	0.7226	0.044*
C12	−0.18330 (12)	0.1076 (3)	0.56950 (17)	0.0352 (5)
H12	−0.2389	0.0715	0.5740	0.042*
C13	−0.16619 (12)	0.1761 (3)	0.47410 (17)	0.0317 (4)
C14	−0.08416 (13)	0.2293 (3)	0.46589 (17)	0.0304 (4)
H14	−0.0737	0.2735	0.4005	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03422 (13)	0.04959 (16)	0.04628 (16)	−0.00074 (10)	−0.00607 (10)	−0.00069 (10)
O1	0.0456 (9)	0.0669 (12)	0.0280 (8)	−0.0112 (8)	0.0110 (7)	−0.0009 (7)
O2	0.0392 (8)	0.0719 (12)	0.0331 (8)	−0.0078 (8)	0.0005 (6)	0.0088 (8)
O1W	0.0755 (12)	0.0603 (12)	0.0319 (9)	−0.0168 (9)	0.0136 (8)	−0.0011 (8)
N1	0.0289 (10)	0.0796 (18)	0.0962 (19)	0.0066 (10)	0.0174 (11)	0.0289 (14)
N2	0.0246 (8)	0.0455 (11)	0.0279 (9)	−0.0050 (7)	0.0084 (7)	0.0004 (7)
N3	0.0251 (8)	0.0364 (9)	0.0369 (10)	−0.0046 (7)	0.0109 (7)	−0.0024 (7)
C1	0.0260 (9)	0.0326 (11)	0.0294 (10)	−0.0018 (8)	0.0029 (8)	0.0037 (8)
C2	0.0288 (10)	0.0368 (12)	0.0368 (12)	−0.0025 (8)	0.0047 (9)	−0.0015 (9)
C3	0.0394 (12)	0.0462 (13)	0.0447 (14)	0.0069 (10)	0.0156 (10)	0.0046 (10)
C4	0.0267 (10)	0.0430 (13)	0.0593 (15)	0.0052 (9)	0.0101 (10)	0.0219 (11)
C5	0.0277 (11)	0.0473 (14)	0.0599 (16)	−0.0101 (10)	−0.0096 (10)	0.0089 (12)
C6	0.0363 (11)	0.0407 (12)	0.0347 (12)	−0.0045 (9)	−0.0014 (9)	−0.0004 (9)
C7	0.0301 (10)	0.0335 (11)	0.0274 (10)	−0.0026 (8)	0.0049 (8)	0.0004 (8)
C8	0.0294 (10)	0.0361 (11)	0.0326 (11)	−0.0005 (8)	0.0104 (8)	−0.0012 (8)
C9	0.0259 (9)	0.0288 (10)	0.0317 (11)	−0.0011 (7)	0.0086 (8)	−0.0016 (8)
C10	0.0320 (10)	0.0372 (11)	0.0287 (10)	−0.0008 (8)	0.0051 (8)	−0.0008 (8)
C11	0.0362 (11)	0.0447 (13)	0.0327 (11)	−0.0062 (10)	0.0135 (9)	0.0005 (9)
C12	0.0267 (10)	0.0376 (12)	0.0427 (12)	−0.0050 (9)	0.0105 (8)	−0.0052 (10)
C13	0.0267 (9)	0.0319 (11)	0.0347 (11)	0.0006 (8)	0.0021 (8)	−0.0060 (8)
C14	0.0312 (10)	0.0318 (11)	0.0290 (11)	−0.0002 (8)	0.0077 (8)	−0.0003 (8)

Geometric parameters (Å, º) top

Br1—C13	1.902 (2)	C3—C4	1.386 (4)
O1—C7	1.228 (2)	C3—H3	0.9300
O2—C10	1.352 (3)	C4—C5	1.384 (4)
O2—H2O	0.9276	C5—C6	1.377 (3)
O1W—H1W1	0.8893	C5—H5	0.9300
O1W—H2W1	0.9036	C6—H6	0.9300
N1—C4	1.393 (3)	C8—C9	1.457 (3)
N1—H1N1	0.8915	C8—H7	0.9300
N1—H2N1	0.8923	C9—C14	1.394 (3)
N2—C7	1.350 (3)	C9—C10	1.405 (3)
N2—N3	1.378 (2)	C10—C11	1.387 (3)
N2—H2N	0.8985	C11—C12	1.380 (3)
N3—C8	1.273 (3)	C11—H11	0.9300
C1—C6	1.392 (3)	C12—C13	1.378 (3)
C1—C2	1.392 (3)	C12—H12	0.9300
C1—C7	1.478 (3)	C13—C14	1.378 (3)
C2—C3	1.376 (3)	C14—H14	0.9300
C2—H2	0.9300

C10—O2—H2O	108.0	C1—C6—H6	119.6
H1W1—O1W—H2W1	103.2	O1—C7—N2	122.64 (19)
C4—N1—H1N1	111.3	O1—C7—C1	121.92 (19)
C4—N1—H2N1	107.5	N2—C7—C1	115.44 (18)
H1N1—N1—H2N1	118.5	N3—C8—C9	121.11 (19)
C7—N2—N3	119.90 (17)	N3—C8—H7	119.4
C7—N2—H2N	123.7	C9—C8—H7	119.4
N3—N2—H2N	116.1	C14—C9—C10	118.67 (18)
C8—N3—N2	116.35 (17)	C14—C9—C8	118.45 (18)
C6—C1—C2	118.00 (19)	C10—C9—C8	122.82 (18)
C6—C1—C7	119.32 (19)	O2—C10—C11	117.74 (19)
C2—C1—C7	122.52 (18)	O2—C10—C9	122.36 (18)
C3—C2—C1	121.0 (2)	C11—C10—C9	119.90 (19)
C3—C2—H2	119.5	C12—C11—C10	120.8 (2)
C1—C2—H2	119.5	C12—C11—H11	119.6
C2—C3—C4	120.8 (2)	C10—C11—H11	119.6
C2—C3—H3	119.6	C13—C12—C11	119.30 (18)
C4—C3—H3	119.6	C13—C12—H12	120.3
C5—C4—C3	118.5 (2)	C11—C12—H12	120.3
C5—C4—N1	121.8 (2)	C12—C13—C14	121.08 (19)
C3—C4—N1	119.7 (3)	C12—C13—Br1	119.59 (15)
C6—C5—C4	120.9 (2)	C14—C13—Br1	119.33 (16)
C6—C5—H5	119.5	C13—C14—C9	120.29 (19)
C4—C5—H5	119.5	C13—C14—H14	119.9
C5—C6—C1	120.8 (2)	C9—C14—H14	119.9
C5—C6—H6	119.6

C7—N2—N3—C8	175.72 (19)	N2—N3—C8—C9	175.98 (18)
C6—C1—C2—C3	1.2 (3)	N3—C8—C9—C14	179.08 (19)
C7—C1—C2—C3	−174.1 (2)	N3—C8—C9—C10	−3.7 (3)
C1—C2—C3—C4	−1.1 (3)	C14—C9—C10—O2	179.73 (19)
C2—C3—C4—C5	−0.2 (3)	C8—C9—C10—O2	2.5 (3)
C2—C3—C4—N1	177.1 (2)	C14—C9—C10—C11	0.3 (3)
C3—C4—C5—C6	1.3 (3)	C8—C9—C10—C11	−176.9 (2)
N1—C4—C5—C6	−176.0 (2)	O2—C10—C11—C12	179.6 (2)
C4—C5—C6—C1	−1.2 (4)	C9—C10—C11—C12	−0.9 (3)
C2—C1—C6—C5	−0.1 (3)	C10—C11—C12—C13	0.6 (3)
C7—C1—C6—C5	175.3 (2)	C11—C12—C13—C14	0.3 (3)
N3—N2—C7—O1	−8.8 (3)	C11—C12—C13—Br1	179.78 (16)
N3—N2—C7—C1	170.52 (17)	C12—C13—C14—C9	−0.9 (3)
C6—C1—C7—O1	−30.2 (3)	Br1—C13—C14—C9	179.60 (15)
C2—C1—C7—O1	145.0 (2)	C10—C9—C14—C13	0.6 (3)
C6—C1—C7—N2	150.5 (2)	C8—C9—C14—C13	177.93 (19)
C2—C1—C7—N2	−34.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N3	0.93	1.84	2.660 (2)	145
N2—H2N···O1Wⁱ	0.90	1.93	2.823 (2)	171
N1—H2N1···O1Wⁱⁱ	0.89	2.57	3.276 (3)	137
O1W—H2W1···O1	0.90	1.77	2.653 (2)	167

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂BrN₃O₂·H₂O
M_r	352.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	15.8435 (11), 7.1718 (6), 12.6462 (8)
β (°)	101.391 (3)
V (Å³)	1408.64 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.93
Crystal size (mm)	0.32 × 0.26 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.454, 0.565
No. of measured, independent and observed [I > 2σ(I)] reflections	11798, 3138, 2543
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.077, 1.04
No. of reflections	3138
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.49

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N3	0.93	1.84	2.660 (2)	145
N2—H2N···O1Wⁱ	0.90	1.93	2.823 (2)	171
N1—H2N1···O1Wⁱⁱ	0.89	2.57	3.276 (3)	137
O1W—H2W1···O1	0.90	1.77	2.653 (2)	167

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

Footnotes

‡Present address: Structural Dynamics of (Bio)Chemical Systems, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Göttingen, Germany.

Acknowledgements

HK thanks PNU for financial support. MNT thanks GC University of Sargodha, Pakistan, for the research facility.

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