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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 6| June 2016| x160838
doi:10.1107/S2414314616008385

2-[(2-Fluoro­phen­yl)(1H-indol-3-yl)meth­yl]-1H-indole

R. Anil Kumar,a S. Naveen,b T. O. Shrungesh Kumar,a K. M. Mahadevan,a M. N. Kumarac and N. K. Lokanathd*

aDepartment of Chemistry, Kuvempu University, P G Centre, Kadur 577 548, India, bInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, cDepartment of Chemistry, Yuvarajas College, University of Mysore, Mysuru 570 005, India, and dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India
*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 19 May 2016; accepted 23 May 2016; online 3 June 2016)

In the title compound, C23H17FN2, the indole ring systems are oriented orthogonally, as indicated by the dihedral angle between them of 88.49 (5)°. The fluoro­phenyl ring is nearly perpendicular to one of the indole ring systems [dihedral angle = 85.31 (16)°] and twisted by 63.6 (6)° from the other. In the crystal, N—H⋯π, C—H⋯π and C—H⋯F inter­actions occur, forming a three-dimensional network.

CCDC reference: 1481317

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

Structure description

Indoles have diverse biological activities and pharmaceutical applications (Diss et al., 2013[Diss, L. B., Robinson, S. D., Wu, Y., Fidalgo, S., Yeoman, M. S. & Patel, B. A. (2013). ACS Chem. Neurosci. 4, 879-887.]). In particular, bis­(indol­yl) methane and its derivatives are known to be important inter­mediates in organic synthesis and exhibit various physiological properties (Ishikawa et al., 2008[Ishikawa, H., Colby, D. A. & Boger, D. L. (2008). J. Am. Chem. Soc. 130, 420-421.]). As part of our ongoing research in this area (Walki et al., 2015[Walki, S., Naveen, S., Kenchanna, S., Mahadevan, K. M., Kumara, M. N. & Lokanath, N. K. (2015). Acta Cryst. E71, o860-o861.]), the synthesis and crystal structure of the title compound, C23H17N2F, is reported herein (Fig. 1[link]).

[Figure 1]
Figure 1
View of the title compound, with displacement ellipsoids for non-H atoms drawn at the 50% probability level.

Both the indole ring systems are essentially planar with dihedral angles of 1.37 (1) and 2.48 (1)°, between the two fused ring systems N1/C2–C9 and N13/C11/C12/C14–C19, respectively. The indole ring systems are oriented orthogonally with respect to each other, as indicated by the dihedral angle value of 88.49 (5)°. The fluoro­phenyl ring is nearly perpendicular to one of the indole ring systems [N1/C2–C9; dihedral angle = 85.31 (16)°] whereas it is twisted by 63.6 (6)° from the other indole ring system.

In the crystal, the C5—H5⋯F26 hydrogen bond (Table 1[link]) links mol­ecules into R22(18) inversion dimers. C23—H23⋯π chains connect these dimers, forming rectangular columns running down the b axis, and these chains are further reinforced by C24—H24⋯π inter­actions (Fig. 2[link] left). Further N1—H1⋯π and C3—H3⋯π inter­actions between the mol­ecules results in sheets parallel to the bc plane (Fig. 2[link] right). The sheets are inter­linked via N13—H13⋯π inter­actions along the a axis, forming a three-dimensional network (Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/C2/C7–C9, C2–C7, C14–C19 and C20–C25 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5⋯F26i 0.93 2.51 3.3849 (18) 157
N1—H1⋯Cg4ii 0.86 2.63 3.4390 (14) 157
N13—H13⋯Cg3iii 0.86 2.30 3.1539 (14) 170
C3—H3⋯Cg5ii 0.93 2.96 3.7630 (19) 146
C23—H23⋯Cg4iv 0.93 2.68 3.5022 (17) 147
C24—H24⋯Cg1v 0.93 2.93 3.8376 (17) 166
Symmetry codes: (i) -x, -y+2, -z+1; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) -x+1, -y+2, -z+1; (iv) x, y-1, z; (v) -x, -y+1, -z+1.
[Figure 2]
Figure 2
The mol­ecular packing showing R22(18) dimers (left) connected by C—H⋯π inter­actions forming rectangular columns (right). Hydrogen bonds are shown as blue lines.
[Figure 3]
Figure 3
Packing of the mol­ecules viewed along the a axis.

Synthesis and crystallization

To a flask containing 5 ml of glacial acetic acid, indole (2 mmol, 0.23 g) was added under stirring until all the indole had dissolved. Then 2-fluoro­benzaldehyde (1 mmol, 0.14 g) was added under vigorous stirring. The reaction mixture was allowed to stir over 4 to 6 h, during which time the reaction solution turned from light yellow to light pink to dark red colour. The product was detected by TLC (100% CH2Cl2). After the completion of the reaction, the reaction mixture was added to ice-cold water. The product that separated out from the reaction mixture was filtered and washed with water. The crude product was further purified by recrystallization using methanol as solvent to obtain orange blocks of the title compound in 81% yield, m.p. = 178–180°C.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C23H17FN2
Mr 340.39
Crystal system, space group Monoclinic, P21/c
Temperature (K) 296
a, b, c (Å) 10.0822 (5), 9.7969 (4), 17.6310 (8)
β (°) 94.262 (2)
V (Å3) 1736.67 (14)
Z 4
Radiation type Cu Kα
μ (mm−1) 0.67
Crystal size (mm) 0.29 × 0.27 × 0.25
 
Data collection
Diffractometer Bruker X8 Proteum
Absorption correction Multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.823, 0.845
No. of measured, independent and observed [I > 2σ(I)] reflections 7737, 2845, 2480
Rint 0.036
(sin θ/λ)max (Å−1) 0.584
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.105, 1.07
No. of reflections 2845
No. of parameters 235
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.23, −0.18
Computer programs: APEX2 and SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data

CCDC reference: 1481317

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616008385/hb4049sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616008385/hb4049Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616008385/hb4049Isup3.cml

checkCIF report


Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

2-[(2-Fluorophenyl)(1H-indol-3-yl)methyl]-1H-indole top
Crystal data top
C23H17FN2F(000) = 712
Mr = 340.39Dx = 1.302 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 2845 reflections
a = 10.0822 (5) Åθ = 4.4–64.2°
b = 9.7969 (4) ŵ = 0.67 mm−1
c = 17.6310 (8) ÅT = 296 K
β = 94.262 (2)°Block, orange
V = 1736.67 (14) Å30.29 × 0.27 × 0.25 mm
Z = 4
Data collection top
Bruker X8 Proteum
diffractometer		2845 independent reflections
Radiation source: Rotating Anode2480 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 18.4 pixels mm-1θmax = 64.2°, θmin = 4.4°
φ and ω scansh = −11→11
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		k = −10→11
Tmin = 0.823, Tmax = 0.845l = −20→11
7737 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0587P)2 + 0.3295P]
where P = (Fo2 + 2Fc2)/3
2845 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/Ueq
F260.00536 (8)0.57139 (8)0.42643 (5)0.0316 (3)
N10.24195 (13)0.72377 (13)0.64897 (7)0.0302 (4)
N130.52338 (12)0.93784 (13)0.38606 (7)0.0292 (4)
C20.20504 (14)0.85811 (15)0.64054 (9)0.0260 (4)
C30.18320 (15)0.95771 (17)0.69494 (10)0.0334 (5)
C40.15144 (15)1.08692 (17)0.66901 (11)0.0358 (5)
C50.14059 (15)1.11795 (16)0.59132 (11)0.0343 (5)
C60.16105 (14)1.01950 (15)0.53726 (9)0.0271 (4)
C70.19387 (13)0.88639 (14)0.56189 (8)0.0227 (4)
C80.22413 (13)0.76180 (14)0.52312 (8)0.0218 (4)
C90.25164 (15)0.66702 (15)0.57843 (9)0.0270 (4)
C100.22554 (14)0.74567 (14)0.43815 (8)0.0220 (4)
C110.33021 (14)0.83498 (14)0.40622 (8)0.0228 (4)
C120.46077 (14)0.84799 (15)0.43141 (9)0.0276 (5)
C140.43318 (14)0.98676 (14)0.33069 (8)0.0242 (4)
C150.44803 (16)1.08041 (15)0.27228 (9)0.0295 (5)
C160.33645 (16)1.11427 (15)0.22625 (9)0.0304 (5)
C170.21197 (16)1.05838 (15)0.23816 (9)0.0294 (4)
C180.19700 (14)0.96412 (14)0.29521 (8)0.0244 (4)
C190.30918 (14)0.92501 (14)0.34225 (8)0.0215 (4)
C200.23638 (14)0.59460 (14)0.41749 (8)0.0232 (4)
C210.35517 (16)0.52949 (16)0.40449 (9)0.0310 (5)
C220.35997 (17)0.39047 (17)0.38958 (10)0.0369 (5)
C230.24583 (17)0.31272 (16)0.38742 (10)0.0349 (5)
C240.12536 (16)0.37375 (16)0.39988 (9)0.0300 (5)
C250.12406 (14)0.51209 (15)0.41452 (8)0.0246 (4)
H10.256700.681900.691600.0360*
H30.189900.937500.746600.0400*
H40.136801.155400.704000.0430*
H50.119201.206500.575800.0410*
H60.153301.040800.485700.0330*
H90.273900.576500.569700.0320*
H100.139100.777600.415900.0260*
H120.501500.802600.473200.0330*
H130.606100.959900.391600.0350*
H150.530401.118700.264700.0350*
H160.344001.175500.186500.0360*
H170.137901.085200.207100.0350*
H180.113900.927100.302400.0290*
H210.433200.580300.405800.0370*
H220.440700.349600.381000.0440*
H230.249600.219600.377600.0420*
H240.047400.322800.398400.0360*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F260.0230 (4)0.0280 (4)0.0438 (6)−0.0020 (3)0.0034 (4)−0.0013 (4)
N10.0418 (8)0.0289 (7)0.0201 (7)−0.0057 (5)0.0031 (6)0.0031 (5)
N130.0192 (6)0.0338 (7)0.0345 (8)−0.0060 (5)0.0005 (5)0.0060 (6)
C20.0235 (7)0.0278 (7)0.0273 (8)−0.0067 (6)0.0059 (6)−0.0036 (6)
C30.0283 (8)0.0424 (9)0.0307 (9)−0.0117 (7)0.0099 (7)−0.0111 (7)
C40.0244 (8)0.0356 (9)0.0487 (11)−0.0057 (7)0.0109 (7)−0.0194 (8)
C50.0216 (7)0.0265 (8)0.0550 (11)0.0008 (6)0.0036 (7)−0.0081 (7)
C60.0190 (7)0.0257 (7)0.0363 (9)−0.0011 (6)0.0000 (6)−0.0012 (7)
C70.0170 (7)0.0246 (7)0.0266 (8)−0.0040 (5)0.0029 (6)−0.0025 (6)
C80.0196 (7)0.0220 (7)0.0241 (8)−0.0039 (5)0.0031 (6)−0.0015 (6)
C90.0322 (8)0.0218 (7)0.0273 (8)−0.0025 (6)0.0045 (6)−0.0006 (6)
C100.0213 (7)0.0220 (7)0.0226 (8)−0.0016 (5)0.0013 (6)−0.0002 (6)
C110.0232 (7)0.0237 (7)0.0216 (7)−0.0018 (6)0.0031 (6)−0.0010 (6)
C120.0261 (8)0.0305 (8)0.0258 (8)−0.0027 (6)−0.0011 (6)0.0053 (6)
C140.0247 (7)0.0240 (7)0.0243 (8)0.0000 (6)0.0039 (6)−0.0020 (6)
C150.0298 (8)0.0270 (8)0.0329 (9)−0.0012 (6)0.0098 (7)0.0015 (7)
C160.0405 (9)0.0243 (7)0.0270 (8)0.0026 (6)0.0076 (7)0.0046 (6)
C170.0355 (8)0.0238 (7)0.0279 (8)0.0057 (6)−0.0035 (7)−0.0013 (6)
C180.0251 (7)0.0221 (7)0.0258 (8)−0.0002 (6)0.0013 (6)−0.0039 (6)
C190.0235 (7)0.0205 (7)0.0210 (7)−0.0006 (5)0.0044 (6)−0.0045 (6)
C200.0273 (8)0.0246 (7)0.0177 (7)−0.0019 (6)0.0027 (6)−0.0009 (6)
C210.0290 (8)0.0302 (8)0.0344 (9)−0.0023 (6)0.0070 (7)−0.0048 (7)
C220.0353 (9)0.0331 (8)0.0435 (10)0.0045 (7)0.0114 (8)−0.0071 (7)
C230.0456 (10)0.0256 (8)0.0342 (9)−0.0003 (7)0.0085 (7)−0.0066 (7)
C240.0341 (8)0.0263 (8)0.0299 (8)−0.0072 (6)0.0037 (7)−0.0046 (6)
C250.0239 (7)0.0285 (8)0.0215 (8)0.0008 (6)0.0024 (6)−0.0009 (6)
Geometric parameters (Å, º) top
F26—C251.3606 (16)C17—C181.382 (2)
N1—C21.3728 (19)C18—C191.405 (2)
N1—C91.372 (2)C20—C251.389 (2)
N13—C121.3739 (19)C20—C211.391 (2)
N13—C141.3703 (19)C21—C221.389 (2)
N1—H10.8600C22—C231.378 (2)
N13—H130.8600C23—C241.386 (2)
C2—C31.397 (2)C24—C251.380 (2)
C2—C71.410 (2)C3—H30.9300
C3—C41.376 (2)C4—H40.9300
C4—C51.399 (3)C5—H50.9300
C5—C61.382 (2)C6—H60.9300
C6—C71.406 (2)C9—H90.9300
C7—C81.4426 (19)C10—H100.9800
C8—C91.360 (2)C12—H120.9300
C8—C101.508 (2)C15—H150.9300
C10—C111.511 (2)C16—H160.9300
C10—C201.5300 (19)C17—H170.9300
C11—C121.364 (2)C18—H180.9300
C11—C191.435 (2)C21—H210.9300
C14—C191.417 (2)C22—H220.9300
C14—C151.396 (2)C23—H230.9300
C15—C161.378 (2)C24—H240.9300
C16—C171.399 (2)
C2—N1—C9109.10 (12)C10—C20—C21124.09 (13)
C12—N13—C14109.23 (12)C20—C21—C22121.57 (15)
C2—N1—H1125.00C21—C22—C23120.43 (16)
C9—N1—H1125.00C22—C23—C24119.80 (15)
C12—N13—H13125.00C23—C24—C25118.29 (14)
C14—N13—H13125.00F26—C25—C24117.97 (13)
N1—C2—C7107.22 (13)C20—C25—C24124.02 (14)
C3—C2—C7122.18 (14)F26—C25—C20118.01 (12)
N1—C2—C3130.58 (15)C2—C3—H3121.00
C2—C3—C4117.34 (16)C4—C3—H3121.00
C3—C4—C5121.64 (16)C3—C4—H4119.00
C4—C5—C6121.24 (15)C5—C4—H4119.00
C5—C6—C7118.55 (15)C4—C5—H5119.00
C2—C7—C8107.18 (12)C6—C5—H5119.00
C6—C7—C8133.75 (13)C5—C6—H6121.00
C2—C7—C6119.05 (13)C7—C6—H6121.00
C9—C8—C10128.64 (13)N1—C9—H9125.00
C7—C8—C9106.08 (13)C8—C9—H9125.00
C7—C8—C10125.28 (12)C8—C10—H10107.00
N1—C9—C8110.41 (13)C11—C10—H10107.00
C8—C10—C20110.13 (11)C20—C10—H10107.00
C11—C10—C20114.02 (12)N13—C12—H12125.00
C8—C10—C11111.58 (11)C11—C12—H12125.00
C10—C11—C12128.07 (13)C14—C15—H15121.00
C10—C11—C19125.60 (12)C16—C15—H15121.00
C12—C11—C19106.33 (13)C15—C16—H16119.00
N13—C12—C11110.15 (13)C17—C16—H16119.00
N13—C14—C15130.82 (14)C16—C17—H17119.00
C15—C14—C19122.07 (13)C18—C17—H17119.00
N13—C14—C19107.10 (12)C17—C18—H18121.00
C14—C15—C16117.73 (14)C19—C18—H18120.00
C15—C16—C17121.30 (14)C20—C21—H21119.00
C16—C17—C18121.22 (14)C22—C21—H21119.00
C17—C18—C19119.02 (13)C21—C22—H22120.00
C14—C19—C18118.60 (13)C23—C22—H22120.00
C11—C19—C14107.16 (12)C22—C23—H23120.00
C11—C19—C18134.18 (13)C24—C23—H23120.00
C10—C20—C25119.96 (12)C23—C24—H24121.00
C21—C20—C25115.88 (13)C25—C24—H24121.00
C9—N1—C2—C3−179.64 (15)C8—C10—C20—C2580.00 (16)
C9—N1—C2—C7−1.13 (16)C11—C10—C20—C2129.6 (2)
C2—N1—C9—C81.08 (17)C11—C10—C20—C25−153.68 (13)
C14—N13—C12—C110.86 (17)C10—C11—C12—N13178.93 (13)
C12—N13—C14—C15179.23 (15)C19—C11—C12—N13−1.51 (17)
C12—N13—C14—C190.18 (16)C10—C11—C19—C14−178.85 (13)
N1—C2—C3—C4177.56 (15)C10—C11—C19—C184.2 (3)
C7—C2—C3—C4−0.8 (2)C12—C11—C19—C141.58 (16)
N1—C2—C7—C6−177.98 (12)C12—C11—C19—C18−175.37 (16)
N1—C2—C7—C80.77 (15)N13—C14—C15—C16−177.53 (15)
C3—C2—C7—C60.7 (2)C19—C14—C15—C161.4 (2)
C3—C2—C7—C8179.44 (13)N13—C14—C19—C11−1.08 (15)
C2—C3—C4—C50.3 (2)N13—C14—C19—C18176.43 (12)
C3—C4—C5—C60.2 (2)C15—C14—C19—C11179.76 (13)
C4—C5—C6—C7−0.3 (2)C15—C14—C19—C18−2.7 (2)
C5—C6—C7—C2−0.2 (2)C14—C15—C16—C170.9 (2)
C5—C6—C7—C8−178.49 (15)C15—C16—C17—C18−1.9 (2)
C2—C7—C8—C9−0.14 (15)C16—C17—C18—C190.5 (2)
C2—C7—C8—C10−179.35 (13)C17—C18—C19—C11178.41 (15)
C6—C7—C8—C9178.35 (15)C17—C18—C19—C141.7 (2)
C6—C7—C8—C10−0.9 (2)C10—C20—C21—C22176.78 (15)
C7—C8—C9—N1−0.56 (16)C25—C20—C21—C22−0.1 (2)
C10—C8—C9—N1178.62 (13)C10—C20—C25—F263.4 (2)
C7—C8—C10—C1162.75 (17)C10—C20—C25—C24−176.90 (14)
C7—C8—C10—C20−169.58 (12)C21—C20—C25—F26−179.62 (13)
C9—C8—C10—C11−116.29 (16)C21—C20—C25—C240.1 (2)
C9—C8—C10—C2011.4 (2)C20—C21—C22—C23−0.1 (3)
C8—C10—C11—C1249.0 (2)C21—C22—C23—C240.3 (3)
C8—C10—C11—C19−130.47 (14)C22—C23—C24—C25−0.3 (2)
C20—C10—C11—C12−76.54 (19)C23—C24—C25—F26179.77 (14)
C20—C10—C11—C19103.98 (16)C23—C24—C25—C200.1 (2)
C8—C10—C20—C21−96.71 (16)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/C2/C7–C9, C2–C7, C14–C19 and C20–C25 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C5—H5···F26i0.932.513.3849 (18)157
N1—H1···Cg4ii0.862.633.4390 (14)157
N13—H13···Cg3iii0.862.303.1539 (14)170
C3—H3···Cg5ii0.932.963.7630 (19)146
C23—H23···Cg4iv0.932.683.5022 (17)147
C24—H24···Cg1v0.932.933.8376 (17)166
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, −y+3/2, z+1/2; (iii) −x+1, −y+2, −z+1; (iv) x, y−1, z; (v) −x, −y+1, −z+1.
 

Acknowledgements

The authors are thankful to the IOE, Vijnana Bhavana, University of Mysore, for providing the single-crystal X-ray diffractometer facility. RAK thanks the UGC, New Delhi, for financial support through a BSR fellowship.

References

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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.

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ISSN: 2414-3146
Volume 1| Part 6| June 2016| x160838
doi:10.1107/S2414314616008385
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