2,3,4,9-Tetra­hydro-1H-carbazole

Murugavel, S.; Kannan, P.S.; SubbiahPandi, A.; Surendiran, T.; Balasubramanian, S.

doi:10.1107/S1600536808038713

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2433

doi:10.1107/S1600536808038713

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2,3,4,9-Tetrahydro-1H-carbazole

S. Murugavel,^a P. S. Kannan,^b A. SubbiahPandi,^c ^* T. Surendiran ^d and S. Balasubramanian ^e

^aDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, ^bDepartment of Physics, SMK Fomra Institute of Technology, Thaiyur, Chennai 603 103, India, ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^dDepartment of Chemistry, Sathyabama University, Jeppiaar Nagar, Chennai 600 119, India, and ^eDepartment of Chemistry, Mohamed Sathak A. J. College of Engineering, Egattur, Chennai 603 103, India
^*Correspondence e-mail: a_spandian@yahoo.com

(Received 31 October 2008; accepted 19 November 2008; online 26 November 2008)

In the title compound, C₁₂H₁₃N, two methylene C atoms of the cyclohexene ring are disordered over two sites with occupancies of 0.591 (10) and 0.409 (10); both disorder components adopt half-chair conformations. The crystal structure is stabilized by intermolecular N—H⋯π and C—H⋯π interactions.

Related literature

For a related structure, see: Arulmozhi et al. (2008 ). For general background, see: Mi et al. (2003 ); Hewlins et al. (1984 ); Mohanakrishnan & Srinivasan (1995a ,b ); Kansal & Potier (1986 ); Phillipson & Zenk (1980 ); Saxton (1983 ); Abraham (1975 ).

Experimental

Crystal data

C₁₂H₁₃N
M_r = 171.23
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.1067 (4) Å
b = 7.9488 (5) Å
c = 19.4512 (12) Å
V = 944.18 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 (2) K
0.26 × 0.15 × 0.15 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: none
13269 measured reflections
1777 independent reflections
1323 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.123
S = 1.07
1777 reflections
137 parameters
15 restraints
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cg2ⁱ	0.86	2.62	3.327 (1)	140
C4—H4⋯Cg1ⁱ	0.93	2.86	3.645 (1)	143
C12—H12B⋯Cg2ⁱⁱ	0.97	2.83	3.577 (2)	135
C12—H12D⋯Cg2ⁱⁱ	0.96	2.72	3.577 (2)	149
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .Cg1 and Cg2 are the centroids of the N1/C5–C8 and C1–C6 rings, respectively.

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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038713/ci2708sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038713/ci2708Isup2.hkl

checkCIF report

Comment top

Carbazole derivatives exhibit good charge transfer and hole transporting properties, which are being explored for a multitude of optoelectronic and photocatalytic applications, including organic light emitting diodes (OLEDs) (Mi et al., 2003). In carbazole derivatives, the preliminary study shows that the presence of oxygenated substituents increases their biological activity (Hewlins et al., 1984). The 2,3-disubstituted indoles have been used as bidentate synthons for the synthesis of various medicinally important carbazole alkaloids (Mohanakrishnan & Srinivasan, 1995a,b). Intercalation between the base pairs in DNA has been implicated for their anticancer activity. It was conceived that the benzo[b] carbazoles as isosteric analogs of pyrido[4,3-b]carbazoles, with oxygenated D-ring could mimic the anti-cancer activity of ellipticine. So it was of interest to study the anticancer activity of D-ring oxygenated benzo[b]carbazoles as it is believed that these molecules could form a stable intercalation complex with DNA (Kansal & Potier, 1986). Tetrahydrocarbazole derivatives are present in the framework of indole-type alkaloids of biological interest (Phillipson & Zenk, 1980; Saxton, 1983; Abraham, 1975). We report here the crystal structure of the title compound (Fig. 1).

Bond lengths are normal and are comparable to the corresponding values observed in 1-naphthyl-9H-carbazole-4-sulfonate (Arulmozhi et al., 2008). The dihedral angle between the C1–C6 and N1/C5—C8 rings is 0.6 (1)°. Both the major and minor conformers of the disordered cyclohexene ring adopt half-chair conformations.

The crystal structure is stabilized by intermolecular N—H···π and C–H···π interactions (Table 1).

Related literature top

For a related structure, see: Arulmozhi et al. (2008). For general background, see: Mi et al. (2003); Hewlins et al. (1984); Mohanakrishnan & Srinivasan (1995a,b); Kansal & Potier (1986); Phillipson & Zenk (1980); Saxton (1983); Abraham (1975). Cg1 and Cg2 are the centroids of the N1/C5–C8 and C1–C6 rings,

respectively.

Experimental top

A mixture of cyclohexanone (0.12 mol) and glacial acetic acid (40 ml) was heated and then redistilled phenylhydrazine (0.1 mol) was added dropwise for 30 min. The mixture was refluxed on a water bath for a further period of 30 min. The reaction mixture was poured into ice-cold water with continuous stirring and brown-coloured solid separated out. It was filtered, washed repeatedly with water and recrystallized from methanol in the presence of a little decolorized carbon to give the title compound. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids. Both disorder components are shown.

2,3,4,9-Tetrahydro-1H-carbazole top

Crystal data top

C₁₂H₁₃N	F(000) = 368
M_r = 171.23	D_x = 1.205 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1778 reflections
a = 6.1067 (4) Å	θ = 2.1–31.1°
b = 7.9488 (5) Å	µ = 0.07 mm⁻¹
c = 19.4512 (12) Å	T = 293 K
V = 944.18 (10) Å³	Block, colourless
Z = 4	0.26 × 0.15 × 0.15 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	1323 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 31.1°, θ_min = 2.1°
ω and ϕ scans	h = −8→8
13269 measured reflections	k = −11→11
1777 independent reflections	l = −28→28

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0603P)² + 0.0496P] where P = (F_o² + 2F_c²)/3
1777 reflections	(Δ/σ)_max = 0.001
137 parameters	Δρ_max = 0.14 e Å⁻³
15 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₂H₁₃N	V = 944.18 (10) Å³
M_r = 171.23	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.1067 (4) Å	µ = 0.07 mm⁻¹
b = 7.9488 (5) Å	T = 293 K
c = 19.4512 (12) Å	0.26 × 0.15 × 0.15 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	1323 reflections with I > 2σ(I)
13269 measured reflections	R_int = 0.036
1777 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	15 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.07	Δρ_max = 0.14 e Å⁻³
1777 reflections	Δρ_min = −0.20 e Å⁻³
137 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	Occ. (<1)
N1	0.7448 (2)	0.5987 (2)	0.95685 (8)	0.0547 (4)
H1A	0.8656	0.6513	0.9495	0.066*
C1	0.3210 (3)	0.4486 (2)	1.06567 (10)	0.0557 (5)
H1	0.1945	0.3846	1.0604	0.067*
C2	0.3803 (4)	0.5087 (3)	1.12920 (10)	0.0634 (5)
H2	0.2921	0.4854	1.1670	0.076*
C3	0.5689 (4)	0.6033 (3)	1.13826 (10)	0.0619 (5)
H3	0.6046	0.6419	1.1820	0.074*
C4	0.7035 (3)	0.6410 (2)	1.08415 (10)	0.0568 (5)
H4	0.8298	0.7045	1.0904	0.068*
C5	0.6448 (3)	0.5811 (2)	1.01954 (9)	0.0457 (4)
C6	0.4535 (3)	0.4849 (2)	1.00903 (9)	0.0429 (4)
C7	0.4433 (3)	0.4464 (2)	0.93742 (8)	0.0429 (4)
C8	0.6210 (3)	0.5184 (2)	0.90741 (9)	0.0473 (4)
C9	0.6730 (3)	0.5153 (3)	0.83301 (10)	0.0668 (6)
H9A	0.8252	0.4841	0.8267	0.080*	0.591 (10)
H9B	0.6521	0.6267	0.8138	0.080*	0.591 (10)
H9C	0.7893	0.4371	0.8240	0.080*	0.409 (10)
H9D	0.7193	0.6249	0.8182	0.080*	0.409 (10)
C10A	0.5287 (9)	0.3918 (9)	0.7958 (4)	0.0674 (15)	0.591 (10)
H10A	0.5876	0.2795	0.8019	0.101*	0.591 (10)
H10B	0.5318	0.4171	0.7470	0.101*	0.591 (10)
C11A	0.2927 (8)	0.3943 (9)	0.8204 (2)	0.0638 (13)	0.591 (10)
H11A	0.2083	0.3133	0.7941	0.096*	0.591 (10)
H11B	0.2308	0.5049	0.8122	0.096*	0.591 (10)
C10B	0.4709 (17)	0.4587 (13)	0.7953 (5)	0.076 (2)	0.409 (10)
H10C	0.3699	0.5527	0.7924	0.114*	0.409 (10)
H10D	0.5117	0.4282	0.7487	0.114*	0.409 (10)
C11B	0.3543 (15)	0.3125 (11)	0.8276 (3)	0.0651 (19)	0.409 (10)
H11C	0.2313	0.2806	0.7989	0.098*	0.409 (10)
H11D	0.4534	0.2173	0.8300	0.098*	0.409 (10)
C12	0.2741 (3)	0.3519 (3)	0.89757 (10)	0.0579 (5)
H12A	0.1293	0.3817	0.9141	0.069*	0.591 (10)
H12B	0.2943	0.2320	0.9043	0.069*	0.591 (10)
H12C	0.1428	0.4179	0.8941	0.069*	0.409 (10)
H12D	0.2390	0.2494	0.9212	0.069*	0.409 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0455 (8)	0.0620 (9)	0.0565 (9)	−0.0161 (8)	0.0044 (7)	0.0019 (7)
C1	0.0518 (10)	0.0556 (11)	0.0597 (11)	−0.0079 (9)	0.0078 (9)	0.0039 (9)
C2	0.0707 (12)	0.0693 (12)	0.0502 (10)	0.0015 (12)	0.0120 (9)	0.0040 (9)
C3	0.0752 (13)	0.0599 (11)	0.0507 (11)	0.0054 (11)	−0.0054 (10)	−0.0048 (9)
C4	0.0577 (11)	0.0495 (10)	0.0631 (12)	−0.0038 (9)	−0.0095 (10)	−0.0022 (9)
C5	0.0447 (8)	0.0402 (8)	0.0522 (9)	−0.0020 (7)	−0.0005 (7)	0.0042 (7)
C6	0.0425 (8)	0.0374 (7)	0.0488 (8)	0.0012 (7)	0.0007 (7)	0.0036 (7)
C7	0.0422 (8)	0.0379 (8)	0.0487 (9)	0.0013 (7)	−0.0007 (7)	0.0010 (7)
C8	0.0440 (8)	0.0468 (9)	0.0511 (9)	0.0018 (8)	0.0023 (7)	0.0017 (8)
C9	0.0601 (11)	0.0876 (15)	0.0526 (10)	−0.0017 (12)	0.0084 (9)	0.0054 (11)
C10A	0.061 (3)	0.082 (4)	0.059 (2)	0.010 (3)	0.004 (2)	−0.007 (3)
C11A	0.057 (2)	0.076 (3)	0.058 (2)	0.003 (2)	−0.0071 (18)	−0.010 (2)
C10B	0.084 (6)	0.097 (6)	0.046 (3)	0.009 (5)	−0.008 (4)	−0.005 (4)
C11B	0.071 (4)	0.067 (4)	0.057 (3)	0.003 (4)	−0.011 (3)	−0.018 (3)
C12	0.0515 (10)	0.0590 (11)	0.0632 (11)	−0.0084 (9)	−0.0038 (9)	−0.0028 (9)

Geometric parameters (Å, º) top

N1—C5	1.371 (2)	C9—H9B	0.97
N1—C8	1.379 (2)	C9—H9C	0.96
N1—H1A	0.86	C9—H9D	0.96
C1—C2	1.374 (3)	C10A—C11A	1.519 (7)
C1—C6	1.397 (2)	C10A—H10A	0.97
C1—H1	0.93	C10A—H10B	0.97
C2—C3	1.387 (3)	C11A—C12	1.542 (5)
C2—H2	0.93	C11A—H11A	0.97
C3—C4	1.369 (3)	C11A—H11B	0.97
C3—H3	0.93	C10B—C11B	1.501 (10)
C4—C5	1.391 (3)	C10B—H10C	0.97
C4—H4	0.93	C10B—H10D	0.97
C5—C6	1.411 (2)	C11B—C12	1.480 (6)
C6—C7	1.427 (2)	C11B—H11C	0.97
C7—C8	1.359 (2)	C11B—H11D	0.97
C7—C12	1.494 (2)	C12—H12A	0.97
C8—C9	1.482 (3)	C12—H12B	0.97
C9—C10B	1.505 (9)	C12—H12C	0.96
C9—C10A	1.505 (6)	C12—H12D	0.96
C9—H9A	0.97

C5—N1—C8	109.19 (14)	H9C—C9—H9D	108.3
C5—N1—H1A	125.4	C9—C10A—C11A	113.3 (5)
C8—N1—H1A	125.4	C9—C10A—H10A	108.9
C2—C1—C6	118.99 (18)	C11A—C10A—H10A	108.9
C2—C1—H1	120.5	C9—C10A—H10B	108.9
C6—C1—H1	120.5	C11A—C10A—H10B	108.9
C1—C2—C3	121.49 (19)	H10A—C10A—H10B	107.7
C1—C2—H2	119.3	C10A—C11A—C12	112.0 (5)
C3—C2—H2	119.3	C10A—C11A—H11A	109.2
C4—C3—C2	121.30 (18)	C12—C11A—H11A	109.2
C4—C3—H3	119.3	C10A—C11A—H11B	109.2
C2—C3—H3	119.3	C12—C11A—H11B	109.2
C3—C4—C5	117.72 (18)	H11A—C11A—H11B	107.9
C3—C4—H4	121.1	C11B—C10B—C9	114.6 (7)
C5—C4—H4	121.1	C11B—C10B—H10C	108.6
N1—C5—C4	130.84 (17)	C9—C10B—H10C	108.6
N1—C5—C6	107.17 (15)	C11B—C10B—H10D	108.6
C4—C5—C6	121.99 (17)	C9—C10B—H10D	108.6
C1—C6—C5	118.50 (16)	H10C—C10B—H10D	107.6
C1—C6—C7	134.42 (16)	C12—C11B—C10B	112.2 (7)
C5—C6—C7	107.08 (15)	C12—C11B—H11C	109.2
C8—C7—C6	107.10 (14)	C10B—C11B—H11C	109.2
C8—C7—C12	122.77 (16)	C12—C11B—H11D	109.2
C6—C7—C12	130.10 (15)	C10B—C11B—H11D	109.2
C7—C8—N1	109.45 (15)	H11C—C11B—H11D	107.9
C7—C8—C9	125.70 (17)	C11B—C12—C7	110.8 (3)
N1—C8—C9	124.85 (17)	C7—C12—C11A	110.1 (2)
C8—C9—C10B	107.8 (4)	C11B—C12—H12A	131.1
C8—C9—C10A	110.8 (3)	C7—C12—H12A	109.6
C8—C9—H9A	109.5	C11A—C12—H12A	109.6
C10B—C9—H9A	130.4	C11B—C12—H12B	82.7
C10A—C9—H9A	109.5	C7—C12—H12B	109.6
C8—C9—H9B	109.5	C11A—C12—H12B	109.6
C10B—C9—H9B	88.7	H12A—C12—H12B	108.1
C10A—C9—H9B	109.5	C11B—C12—H12C	109.1
H9A—C9—H9B	108.1	C7—C12—H12C	109.8
C8—C9—H9C	110.3	C11A—C12—H12C	82.8
C10B—C9—H9C	109.0	H12B—C12—H12C	130.7
C10A—C9—H9C	85.6	C11B—C12—H12D	109.5
H9B—C9—H9C	128.2	C7—C12—H12D	109.4
C8—C9—H9D	109.9	C11A—C12—H12D	131.9
C10B—C9—H9D	111.5	H12A—C12—H12D	81.1
C10A—C9—H9D	128.3	H12C—C12—H12D	108.1
H9A—C9—H9D	84.9

C6—C1—C2—C3	−0.4 (3)	C5—N1—C8—C7	−1.0 (2)
C1—C2—C3—C4	0.1 (3)	C5—N1—C8—C9	177.78 (18)
C2—C3—C4—C5	0.0 (3)	C7—C8—C9—C10B	14.1 (5)
C8—N1—C5—C4	−178.92 (19)	N1—C8—C9—C10B	−164.5 (5)
C8—N1—C5—C6	0.7 (2)	C7—C8—C9—C10A	−11.7 (4)
C3—C4—C5—N1	179.77 (19)	N1—C8—C9—C10A	169.7 (3)
C3—C4—C5—C6	0.2 (3)	C8—C9—C10A—C11A	40.6 (8)
C2—C1—C6—C5	0.6 (3)	C10B—C9—C10A—C11A	−46.8 (11)
C2—C1—C6—C7	−179.34 (19)	C9—C10A—C11A—C12	−59.6 (9)
N1—C5—C6—C1	179.87 (15)	C8—C9—C10B—C11B	−43.8 (11)
C4—C5—C6—C1	−0.4 (3)	C10A—C9—C10B—C11B	57.5 (12)
N1—C5—C6—C7	−0.20 (18)	C9—C10B—C11B—C12	61.8 (14)
C4—C5—C6—C7	179.48 (17)	C10B—C11B—C12—C7	−42.9 (10)
C1—C6—C7—C8	179.52 (19)	C10B—C11B—C12—C11A	51.4 (8)
C5—C6—C7—C8	−0.39 (18)	C8—C7—C12—C11B	14.2 (5)
C1—C6—C7—C12	1.6 (3)	C6—C7—C12—C11B	−168.1 (5)
C5—C6—C7—C12	−178.35 (17)	C8—C7—C12—C11A	−17.0 (4)
C6—C7—C8—N1	0.84 (19)	C6—C7—C12—C11A	160.7 (3)
C12—C7—C8—N1	178.98 (16)	C10A—C11A—C12—C11B	−51.7 (7)
C6—C7—C8—C9	−177.92 (18)	C10A—C11A—C12—C7	45.1 (7)
C12—C7—C8—C9	0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cg2ⁱ	0.86	2.62	3.327 (1)	140
C4—H4···Cg1ⁱ	0.93	2.86	3.645 (1)	143
C12—H12B···Cg2ⁱⁱ	0.97	2.83	3.577 (2)	135
C12—H12D···Cg2ⁱⁱ	0.96	2.72	3.577 (2)	149

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃N
M_r	171.23
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.1067 (4), 7.9488 (5), 19.4512 (12)
V (Å³)	944.18 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.26 × 0.15 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13269, 1777, 1323
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.727

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.123, 1.07
No. of reflections	1777
No. of parameters	137
No. of restraints	15
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.20

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cg2ⁱ	0.86	2.62	3.327 (1)	140
C4—H4···Cg1ⁱ	0.93	2.86	3.645 (1)	143
C12—H12B···Cg2ⁱⁱ	0.97	2.83	3.577 (2)	135
C12—H12D···Cg2ⁱⁱ	0.96	2.72	3.577 (2)	149

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

Acknowledgements

The authors are grateful to Dr J. Jothi Kumar, Principal of Presidency College (Autonomous), Chennai, for providing computer and internet facilities. Dr Babu Vargheese, SAIF, IIT-Madras, India, is thanked for his help with the data collection.

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