Crystal structure of 2-phenyl­ethyl­amin­ium 4-nitro­phenolate monohydrate

Sowmya, N.S.; Sampathkrishnan, S.; Sudhahar, S.; Kumar, R.M.; Chakkaravarthi, G.

doi:10.1107/S1600536814025318

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 12| December 2014| Page o1280

doi:10.1107/S1600536814025318

Open

access

Crystal structure of 2-phenylethylaminium 4-nitrophenolate monohydrate

N. Swarna Sowmya,^a S. Sampathkrishnan,^a S. Sudhahar,^b R. Mohan Kumar ^b ^* and G. Chakkaravarthi ^c ^*

^aDepartment of Applied Physics, Sri Venkateswara College of Engineering, Chennai 602 117, India, ^bDepartment of Physics, Presidency College, Chennai 600 005, India, and ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: mohan66@hotmail.com, chakkaravarthi_2005@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 November 2014; accepted 18 November 2014; online 21 November 2014)

In the title hydrated molecular salt, C₈H₁₂N⁺·C₆H₄NO₃⁻·H₂O, the conformation of the side chain in the cation is anti [C—C—C—N = 179.62 (12)°] and the dihedral angle between the aromatic ring and the nitro group in the anion is 3.34 (11)°. In the crystal, the components are linked by O—H⋯O and N—H⋯O hydrogen bonds, generating (10-1) sheets, which feature R₄⁴(21) loops. The sheets interact by weak aromatic π–π stacking interactions [centroid–centroid distance = 3.896 (3) Å], forming a three-dimensional network.

Keywords: crystal structure; 2-phenylethylaminium; 4-nitrophenolate; hydrated salt; O—H⋯O and N—H⋯O hydrogen bonds; π–π stacking interactions.

CCDC reference: 1034880

1. Related literature

For related structures, see: Kanagathara et al. (2012 ); Lejon et al. (2006 ); Sankar et al. (2014 ); Smith et al. (2003 ).

2. Experimental

2.1. Crystal data

C₈H₁₂N⁺·C₆H₄NO₃⁻·H₂O
M_r = 278.30
Monoclinic, C 2/c
a = 30.381 (5) Å
b = 6.100 (4) Å
c = 21.357 (5) Å
β = 131.876 (5)°
V = 2947 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.26 × 0.24 × 0.20 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.976, T_max = 0.982
14174 measured reflections
3675 independent reflections
2748 reflections with I > 2σ(I)
R_int = 0.021

2.3. Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.124
S = 1.03
3675 reflections
200 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.90 (1)	1.81 (1)	2.7108 (17)	176 (18)
O4—H4B⋯O1	0.84 (1)	1.90 (1)	2.7262 (18)	173 (2)
N1—H1B⋯O2ⁱ	0.90 (1)	2.11 (1)	2.8937 (17)	145 (15)
N1—H1C⋯O4ⁱⁱ	0.91 (1)	1.84 (1)	2.742 (2)	172 (18)
O4—H4A⋯O1ⁱⁱⁱ	0.83 (1)	1.93 (1)	2.7574 (16)	175 (2)
Symmetry codes: (i) -x, -y+2, -z; (ii) x, y-1, z; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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

CCDC reference: 1034880

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814025318/hb7318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814025318/hb7318Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814025318/hb7318Isup3.cml

checkCIF report

Structural commentary top

The geometric parameters of the title compound (I) (Fig.1) are comparable with the reported similar structures (Kanagathara et al., 2012; Sankar et al., 2014; Lejon et al., 2006; Smith et al., 2003). The cation is protonated at N1 atom. The dihedral angle between the two benzene rings (C1—C6) and (C9—C14) is 3.71 (11)°. In the anion, the nitro group (N2/O2/O3) is twisted at an angle of 3.34 (11)° with the benzene ring (C9—C14).

Supramolecular features top

In the molecular structure, weak N—H···O and O—H···O hydrogen bonds link the cation, anion and water molecule which generates S(6) graph set motif. In the crystal structure, N—H···O and O—H···O hydrogen bonds link the anions, cations and water molecules into sheets, parallel to ac plane and further theses sheets are linked by O—H···O hydrogen bonds along [0 1 0] (Table 2 & Fig. 2). The N—H···O hydrogen bonds generates R₄⁴(21) graph-set motif (Fig. 2).

The crystal structure also features weak C—H···π (Table 2) and π–π [Cg2···Cg2ⁱ distance = 3.896 (3)Å; (i) -x,2-y,-z; Cg2 is the centroid of the C9—C14 ring] interactions to form a three dimensional network.

Synthesis and crystallization top

2-Phenylethylamine (1.26 g) and 4-nitrophenol (1.39 g) were disssolved in methanol and colourless blocks of the title compound were grown by slow evaporation.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The C-bound H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 and 0.97 Å for CH_aromatic and CH₂, respectively with U_iso(H) = 1.2Ueq(C). The H atoms bound to O and N atoms were found in a difference map and refined isotropically, with U_iso(H) = 1.5Ueq(O) and distance restraints: O—H = 0.82 (1)Å and N—H = 0.88 (1)Å. The components of the anisotropic displacement parameters in the direction of the bond between C3 and C4 were restrained to be equal within an effective standard deviation of 0.001 using the DELU command in SHELXL97 (Sheldrick, 2008).

Related literature top

For related structures, see: Kanagathara et al. (2012); Lejon et al. (2006); Sankar et al. (2014); Smith et al. (2003).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.

Fig. 2. The packing of (I), viewed down b axis. Intermolecular Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

2-Phenylethylaminium 4-nitrophenol monohydrate top

Crystal data top

C₈H₁₂N⁺·C₆H₄NO₃⁻·H₂O	F(000) = 1184
M_r = 278.30	D_x = 1.254 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 359 reflections
a = 30.381 (5) Å	θ = 1.8–28.4°
b = 6.100 (4) Å	µ = 0.09 mm⁻¹
c = 21.357 (5) Å	T = 295 K
β = 131.876 (5)°	Block, colourless
V = 2947 (2) Å³	0.26 × 0.24 × 0.20 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	3675 independent reflections
Radiation source: fine-focus sealed tube	2748 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω and ϕ scan	θ_max = 28.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −38→40
T_min = 0.976, T_max = 0.982	k = −7→8
14174 measured reflections	l = −28→28

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0561P)² + 0.954P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3675 reflections	Δρ_max = 0.21 e Å⁻³
200 parameters	Δρ_min = −0.19 e Å⁻³
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (5)

Crystal data top

C₈H₁₂N⁺·C₆H₄NO₃⁻·H₂O	V = 2947 (2) Å³
M_r = 278.30	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.381 (5) Å	µ = 0.09 mm⁻¹
b = 6.100 (4) Å	T = 295 K
c = 21.357 (5) Å	0.26 × 0.24 × 0.20 mm
β = 131.876 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3675 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2748 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.982	R_int = 0.021
14174 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	6 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.21 e Å⁻³
3675 reflections	Δρ_min = −0.19 e Å⁻³
200 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
C1	0.32367 (5)	0.9073 (2)	0.49756 (8)	0.0480 (3)
C2	0.31910 (8)	1.1138 (3)	0.51903 (11)	0.0709 (4)
H2	0.2885	1.2063	0.4777	0.085*
C3	0.35989 (10)	1.1848 (3)	0.60213 (13)	0.0850 (5)
H3	0.3564	1.3244	0.6159	0.102*
C4	0.40509 (9)	1.0511 (4)	0.66371 (11)	0.0837 (5)
H4	0.4322	1.0990	0.7192	0.100*
C5	0.41005 (7)	0.8477 (4)	0.64310 (10)	0.0770 (5)
H5	0.4407	0.7560	0.6846	0.092*
C6	0.36972 (6)	0.7765 (3)	0.56068 (9)	0.0579 (3)
H6	0.3738	0.6369	0.5476	0.070*
C7	0.28038 (6)	0.8233 (3)	0.40816 (8)	0.0578 (3)
H7A	0.2783	0.9273	0.3719	0.069*
H7B	0.2949	0.6856	0.4052	0.069*
C8	0.21941 (6)	0.7889 (3)	0.37618 (9)	0.0606 (4)
H8A	0.2214	0.6890	0.4133	0.073*
H8B	0.2039	0.9276	0.3763	0.073*
C9	0.12653 (5)	1.0077 (2)	0.10944 (7)	0.0446 (3)
C10	0.10095 (6)	0.8472 (2)	0.04638 (8)	0.0530 (3)
H10	0.1191	0.7110	0.0601	0.064*
C11	0.04981 (6)	0.8868 (2)	−0.03490 (8)	0.0567 (3)
H11	0.0334	0.7782	−0.0756	0.068*
C12	0.02310 (5)	1.0891 (2)	−0.05554 (7)	0.0498 (3)
C13	0.04662 (5)	1.2508 (2)	0.00428 (8)	0.0521 (3)
H13	0.0281	1.3867	−0.0105	0.062*
C14	0.09722 (6)	1.2110 (2)	0.08547 (8)	0.0515 (3)
H14	0.1126	1.3203	0.1257	0.062*
N1	0.17925 (5)	0.6981 (2)	0.28992 (7)	0.0575 (3)
H1A	0.1771 (8)	0.784 (3)	0.2537 (9)	0.081 (5)*
H1B	0.1421 (5)	0.687 (3)	0.2687 (10)	0.079 (5)*
H1C	0.1932 (8)	0.567 (2)	0.2897 (12)	0.087 (6)*
N2	−0.03040 (5)	1.1357 (3)	−0.14047 (8)	0.0693 (4)
O1	0.17576 (4)	0.97214 (16)	0.18676 (5)	0.0576 (3)
O2	−0.05190 (5)	1.3215 (3)	−0.15745 (8)	0.0901 (4)
O3	−0.05367 (6)	0.9919 (3)	−0.19366 (8)	0.1055 (5)
O4	0.23008 (5)	1.3211 (2)	0.29355 (7)	0.0714 (3)
H4A	0.2588 (7)	1.359 (4)	0.2990 (14)	0.107*
H4B	0.2130 (9)	1.221 (3)	0.2576 (11)	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0467 (6)	0.0555 (7)	0.0463 (6)	−0.0004 (5)	0.0329 (6)	0.0024 (5)
C2	0.0845 (11)	0.0564 (9)	0.0748 (10)	0.0107 (8)	0.0544 (10)	0.0094 (7)
C3	0.1192 (15)	0.0617 (10)	0.0949 (12)	−0.0177 (8)	0.0801 (11)	−0.0224 (8)
C4	0.0833 (11)	0.1073 (15)	0.0598 (9)	−0.0306 (9)	0.0474 (9)	−0.0248 (8)
C5	0.0545 (8)	0.1111 (14)	0.0486 (8)	0.0072 (9)	0.0275 (7)	0.0073 (9)
C6	0.0506 (7)	0.0676 (9)	0.0533 (8)	0.0079 (6)	0.0337 (7)	0.0011 (6)
C7	0.0457 (7)	0.0815 (10)	0.0448 (7)	0.0011 (7)	0.0296 (6)	0.0002 (6)
C8	0.0491 (7)	0.0805 (10)	0.0542 (8)	0.0003 (7)	0.0353 (7)	−0.0014 (7)
C9	0.0342 (5)	0.0487 (7)	0.0426 (6)	−0.0014 (5)	0.0222 (5)	0.0067 (5)
C10	0.0499 (7)	0.0454 (7)	0.0563 (7)	0.0011 (5)	0.0324 (6)	0.0035 (6)
C11	0.0539 (7)	0.0599 (8)	0.0485 (7)	−0.0108 (6)	0.0310 (6)	−0.0067 (6)
C12	0.0355 (5)	0.0668 (8)	0.0396 (6)	−0.0029 (5)	0.0220 (5)	0.0074 (6)
C13	0.0403 (6)	0.0557 (7)	0.0517 (7)	0.0098 (5)	0.0273 (6)	0.0100 (6)
C14	0.0434 (6)	0.0512 (7)	0.0461 (7)	0.0006 (5)	0.0242 (6)	−0.0023 (5)
N1	0.0390 (6)	0.0707 (8)	0.0471 (6)	0.0026 (5)	0.0222 (5)	0.0091 (6)
N2	0.0460 (6)	0.1001 (11)	0.0440 (6)	−0.0063 (7)	0.0227 (6)	0.0111 (7)
O1	0.0395 (5)	0.0603 (6)	0.0456 (5)	0.0021 (4)	0.0170 (4)	0.0098 (4)
O2	0.0524 (6)	0.1087 (10)	0.0654 (7)	0.0168 (6)	0.0211 (6)	0.0326 (7)
O3	0.0852 (9)	0.1324 (13)	0.0444 (6)	−0.0151 (9)	0.0207 (6)	−0.0103 (7)
O4	0.0561 (6)	0.0691 (7)	0.0702 (7)	−0.0085 (5)	0.0344 (6)	−0.0119 (5)

Geometric parameters (Å, º) top

C1—C6	1.3761 (19)	C9—C10	1.4066 (19)
C1—C2	1.379 (2)	C9—C14	1.4084 (19)
C1—C7	1.5116 (18)	C10—C11	1.3729 (19)
C2—C3	1.392 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.378 (2)
C3—C4	1.367 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.377 (2)
C4—C5	1.358 (3)	C12—N2	1.4410 (17)
C4—H4	0.9300	C13—C14	1.3677 (18)
C5—C6	1.382 (2)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	N1—H1A	0.901 (9)
C7—C8	1.5010 (19)	N1—H1B	0.895 (9)
C7—H7A	0.9700	N1—H1C	0.908 (9)
C7—H7B	0.9700	N2—O3	1.220 (2)
C8—N1	1.4795 (19)	N2—O2	1.235 (2)
C8—H8A	0.9700	O4—H4A	0.834 (9)
C8—H8B	0.9700	O4—H4B	0.836 (10)
C9—O1	1.3091 (14)

C6—C1—C2	117.79 (14)	H8A—C8—H8B	108.0
C6—C1—C7	119.94 (13)	O1—C9—C10	121.89 (12)
C2—C1—C7	122.27 (13)	O1—C9—C14	121.15 (12)
C1—C2—C3	120.45 (16)	C10—C9—C14	116.96 (11)
C1—C2—H2	119.8	C11—C10—C9	121.59 (13)
C3—C2—H2	119.8	C11—C10—H10	119.2
C4—C3—C2	120.58 (17)	C9—C10—H10	119.2
C4—C3—H3	119.7	C10—C11—C12	119.33 (13)
C2—C3—H3	119.7	C10—C11—H11	120.3
C5—C4—C3	119.38 (16)	C12—C11—H11	120.3
C5—C4—H4	120.3	C13—C12—C11	120.97 (12)
C3—C4—H4	120.3	C13—C12—N2	118.50 (13)
C4—C5—C6	120.29 (17)	C11—C12—N2	120.53 (13)
C4—C5—H5	119.9	C14—C13—C12	119.79 (13)
C6—C5—H5	119.9	C14—C13—H13	120.1
C1—C6—C5	121.51 (15)	C12—C13—H13	120.1
C1—C6—H6	119.2	C13—C14—C9	121.35 (12)
C5—C6—H6	119.2	C13—C14—H14	119.3
C8—C7—C1	113.03 (10)	C9—C14—H14	119.3
C8—C7—H7A	109.0	C8—N1—H1A	112.1 (12)
C1—C7—H7A	109.0	C8—N1—H1B	111.8 (11)
C8—C7—H7B	109.0	H1A—N1—H1B	105.3 (16)
C1—C7—H7B	109.0	C8—N1—H1C	109.7 (12)
H7A—C7—H7B	107.8	H1A—N1—H1C	106.2 (16)
N1—C8—C7	111.13 (11)	H1B—N1—H1C	111.6 (17)
N1—C8—H8A	109.4	O3—N2—O2	121.46 (14)
C7—C8—H8A	109.4	O3—N2—C12	119.74 (16)
N1—C8—H8B	109.4	O2—N2—C12	118.79 (14)
C7—C8—H8B	109.4	H4A—O4—H4B	106 (2)

C6—C1—C2—C3	−0.3 (2)	C9—C10—C11—C12	0.6 (2)
C7—C1—C2—C3	179.97 (14)	C10—C11—C12—C13	−0.67 (19)
C1—C2—C3—C4	0.0 (3)	C10—C11—C12—N2	179.62 (12)
C2—C3—C4—C5	0.2 (3)	C11—C12—C13—C14	0.01 (19)
C3—C4—C5—C6	−0.1 (3)	N2—C12—C13—C14	179.73 (11)
C2—C1—C6—C5	0.4 (2)	C12—C13—C14—C9	0.8 (2)
C7—C1—C6—C5	−179.87 (13)	O1—C9—C14—C13	178.27 (12)
C4—C5—C6—C1	−0.2 (2)	C10—C9—C14—C13	−0.82 (19)
C6—C1—C7—C8	112.74 (15)	C13—C12—N2—O3	−176.42 (14)
C2—C1—C7—C8	−67.52 (18)	C11—C12—N2—O3	3.3 (2)
C1—C7—C8—N1	−177.62 (13)	C13—C12—N2—O2	3.03 (18)
O1—C9—C10—C11	−178.94 (12)	C11—C12—N2—O2	−177.25 (13)
C14—C9—C10—C11	0.15 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.90 (1)	1.81 (1)	2.7108 (17)	176 (18)
O4—H4B···O1	0.84 (1)	1.90 (1)	2.7262 (18)	173 (2)
N1—H1B···O2ⁱ	0.90 (1)	2.11 (1)	2.8937 (17)	145 (15)
N1—H1C···O4ⁱⁱ	0.91 (1)	1.84 (1)	2.742 (2)	172 (18)
O4—H4A···O1ⁱⁱⁱ	0.83 (1)	1.93 (1)	2.7574 (16)	175 (2)

Symmetry codes: (i) −x, −y+2, −z; (ii) x, y−1, z; (iii) −x+1/2, 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—H1A···O1	0.901 (9)	1.812 (10)	2.7108 (17)	176 (18)
O4—H4B···O1	0.836 (10)	1.895 (10)	2.7262 (18)	173 (2)
N1—H1B···O2ⁱ	0.895 (9)	2.112 (12)	2.8937 (17)	145 (15)
N1—H1C···O4ⁱⁱ	0.908 (9)	1.839 (10)	2.742 (2)	172 (18)
O4—H4A···O1ⁱⁱⁱ	0.834 (9)	1.926 (10)	2.7574 (16)	175 (2)

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

Acknowledgements

The authors thank the SAIF, IIT, Madras, for the data collection.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kanagathara, N., Chakkaravarthi, G., Marchewka, M. K., Gunasekaran, S. & Anbalagan, G. (2012). Acta Cryst. E68, o2286. CSD CrossRef IUCr Journals Google Scholar
Lejon, T., Ingebrigtsen, T. & Hansen, L. K. (2006). Acta Cryst. E62, o701–o702. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sankar, A., Ambalatharasu, S., Peramaiyan, G., Chakkaravarthi, G. & Kanagadurai, R. (2014). Acta Cryst. E70, o450. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smith, G., Wermuth, U. D. & White, J. M. (2003). Acta Cryst. E59, o1977–o1979. Web of Science CSD CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 12| December 2014| Page o1280

doi:10.1107/S1600536814025318

Open

access