N-Ethyl-2,2-dimethyl-N-(3-methyl­phen­yl)propanamide

Palakshamurthy, B.S.; Suchetan, P.A.; Sreenivasa, S.; Lokanath, N.K.; Madhu Chakrapani Rao, T.

doi:10.1107/S1600536814001718

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 2| February 2014| Page o223

doi:10.1107/S1600536814001718

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N-Ethyl-2,2-dimethyl-N-(3-methylphenyl)propanamide

B. S. Palakshamurthy,^a P. A. Suchetan,^b S Sreenivasa,^c ^* N. K. Lokanath ^d and T Madhu Chakrapani Rao ^e

^aDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, ^bDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, ^cDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, ^dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India, and ^eTadimety Aromatics Pvt Ltd, Hirehally Industrial Area, Tumkur, Karnataka 572 168, India
^*Correspondence e-mail: drsreenivasa@yahoo.co.in

(Received 24 December 2013; accepted 23 January 2014; online 29 January 2014)

In the title compound, C₁₄H₂₁NO, the conformation across the N—C(O) bond is syn-periplanar, the C—N—C—C torsion being −5.9 (5)°. The atoms of the ethyl group attached to the N atom are disordered over two sets of sites with occupancy ratios of 0.65 (2):0.35 (2) (CH₂) and 0.689 (14):0.311 (14) (CH₃)are linked by very weak C—H⋯O interactions forming C(8) chains along [001]. C—H⋯π interactions link the molecules along the c-axis direction.

CCDC reference: 983181

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the biological activity of amides, see: Manojkumar et al. (2013a ,b ). Amide groups can provide structural rigidity to molecules, see: Sreenivasa et al. (2013 ).

Experimental

Crystal data

C₁₄H₂₁NO
M_r = 219.32
Monoclinic, P 2₁
a = 7.631 (4) Å
b = 10.878 (7) Å
c = 8.350 (3) Å
β = 105.60 (2)°
V = 667.6 (6) Å³
Z = 2
Cu Kα radiation
μ = 0.52 mm⁻¹
T = 294 K
0.22 × 0.20 × 0.16 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.893, T_max = 0.921
3786 measured reflections
2016 independent reflections
1883 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.160
S = 1.06
2016 reflections
172 parameters
55 restraints
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centoid of the benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Oⁱ	0.93	2.62	3.481 (2)	153
C14—H14A⋯Cgⁱⁱ	0.96	2.85	3.769 (8)	161
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); 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: SHELXL97 (Sheldrick, 2008).

Supporting information

CCDC reference: 983181

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814001718/hg5371sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814001718/hg5371Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814001718/hg5371Isup3.cml

checkCIF report

Comment top

Amides are very common in nature, formed easily and provides structural rigidity to the molecules (Sreenivasa et al. 2013). Amides show a broad spectrum of pharmacological properties, including antibacterial (Manojkumar et al. 2013a), anti-inflammatory, antioxidant, analgesic and antiviral activity (Manojkumar et al. 2013b). Keeping this in mind, the crystal structure of the title compound was determined.

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For the biological activity of amides, see: Manojkumar et al. (2013a,b). Amide groups can provide structural rigidity to molecules, see: Sreenivasa et al. (2013).

Experimental top

N-Ethyl-3-methylaniline (1.00g,7.4 mmol) was taken in dry dichloromethane (10 mL) and the solution was cooled to 0 ^oC. To this reaction mixture 2,2-dimethylpropanoyl chloride (0.888 g, 7.4 mmol) in dichloromethane and triethylamine (1.49g, 1.48 mmol) were added slowly and the mixture was heated to 50^oC for 4 hours. Reaction was monitored by TLC. Reaction mixture was cooled and washed with 10% NaHCO₃ solution. The organic layer was separated, dried and concentrated to obtained crude product which was purified by column chromatography using petroleum ether: ethyl acetate (7:3) as eluent. Yellow prisms of the title compound were obtained from slow evapouration of the solution of the compound in petroleum ether: ethyl acetate (7:3).

Structure description top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For the biological activity of amides, see: Manojkumar et al. (2013a,b). Amide groups can provide structural rigidity to molecules, see: Sreenivasa et al. (2013).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level. Only the major components of the disordered atoms are shown.
	Fig. 2. Molecular packing foming C(8) chains with hydrogen bonding shown as dashed lines.
	Fig. 3. Stacking of molecules along c axis through C—H···Cg interactions. Cg is the centroid of the benzene ring. H-atoms not involved in H-bonding are ommitted for clarity.

N-Ethyl-2,2-dimethyl-N-(3-methylphenyl)propanamide top

Crystal data top

C₁₄H₂₁NO	Prism
M_r = 219.32	D_x = 1.091 Mg m⁻³
Monoclinic, P2₁	Melting point: 492 K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54178 Å
a = 7.631 (4) Å	Cell parameters from 172 reflections
b = 10.878 (7) Å	θ = 5.5–65.5°
c = 8.350 (3) Å	µ = 0.52 mm⁻¹
β = 105.60 (2)°	T = 294 K
V = 667.6 (6) Å³	Prism, yellow
Z = 2	0.22 × 0.20 × 0.16 mm
F(000) = 240

Data collection top

Bruker APEXII diffractometer	1883 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 65.5°, θ_min = 5.5°
phi and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→12
T_min = 0.893, T_max = 0.921	l = −9→9
3786 measured reflections	1012 standard reflections every 2 reflections
2016 independent reflections	intensity decay: 1%

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)] = 0.057	H-atom parameters constrained
wR(F²) = 0.160	w = 1/[σ²(F_o²) + (0.093P)² + 0.1495P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2016 reflections	Δρ_max = 0.34 e Å⁻³
172 parameters	Δρ_min = −0.16 e Å⁻³
55 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.018 (4)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₄H₂₁NO	V = 667.6 (6) Å³
M_r = 219.32	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 7.631 (4) Å	µ = 0.52 mm⁻¹
b = 10.878 (7) Å	T = 294 K
c = 8.350 (3) Å	0.22 × 0.20 × 0.16 mm
β = 105.60 (2)°

Data collection top

Bruker APEXII diffractometer	1883 reflections with I > 2σ(I)
Absorption correction: multi-scan (SADABS; Bruker, 2009)	R_int = 0.034
T_min = 0.893, T_max = 0.921	1012 standard reflections every 2 reflections
3786 measured reflections	intensity decay: 1%
2016 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	55 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.06	Δρ_max = 0.34 e Å⁻³
2016 reflections	Δρ_min = −0.16 e Å⁻³
172 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)
O	0.2284 (2)	0.7636 (3)	0.6964 (2)	0.0725 (7)
N	0.4145 (3)	0.7530 (3)	0.9461 (2)	0.0670 (8)
C11	0.5373 (3)	0.7418 (3)	0.6942 (3)	0.0489 (6)
C6	0.8300 (4)	0.8185 (3)	1.2843 (3)	0.0494 (6)
C10	0.3855 (3)	0.7522 (3)	0.7806 (3)	0.0452 (6)
C4	0.5820 (3)	0.7342 (3)	1.0730 (3)	0.0487 (7)
C5	0.6765 (4)	0.8340 (3)	1.1519 (3)	0.0520 (7)
H5	0.6374	0.9128	1.1164	0.062*
C3	0.6371 (4)	0.6191 (3)	1.1298 (3)	0.0586 (8)
H3	0.5716	0.5510	1.0789	0.070*
C2	0.7875 (4)	0.6028 (3)	1.2607 (4)	0.0602 (8)
H2	0.8249	0.5239	1.2975	0.072*
C1	0.8829 (4)	0.7029 (3)	1.3376 (3)	0.0520 (7)
H1	0.9848	0.6916	1.4271	0.062*
C7	0.9325 (5)	0.9283 (4)	1.3690 (5)	0.0834 (11)
H7A	0.9820	0.9109	1.4851	0.125*
H7B	0.8515	0.9974	1.3563	0.125*
H7C	1.0295	0.9472	1.3200	0.125*
C14	0.4518 (6)	0.7552 (8)	0.5111 (5)	0.129 (2)
H14A	0.5454	0.7608	0.4542	0.193*
H14B	0.3787	0.8283	0.4908	0.193*
H14C	0.3766	0.6849	0.4710	0.193*
C13	0.6307 (11)	0.6209 (5)	0.7262 (9)	0.136 (3)
H13A	0.5417	0.5564	0.7079	0.205*
H13B	0.7044	0.6178	0.8392	0.205*
H13C	0.7066	0.6103	0.6523	0.205*
C12	0.6785 (8)	0.8393 (6)	0.7487 (7)	0.135 (3)
H12A	0.7324	0.8325	0.8663	0.202*
H12B	0.6230	0.9187	0.7237	0.202*
H12C	0.7708	0.8293	0.6910	0.202*
C8A	0.2598 (9)	0.7879 (9)	1.0135 (7)	0.052 (2)	0.65 (2)
H8A1	0.1744	0.8395	0.9348	0.063*	0.65 (2)
H8A2	0.3035	0.8329	1.1169	0.063*	0.65 (2)
C8B	0.2459 (15)	0.7104 (19)	1.0046 (14)	0.059 (4)	0.35 (2)
H8B1	0.1529	0.6742	0.9142	0.070*	0.35 (2)
H8B2	0.2801	0.6522	1.0958	0.070*	0.35 (2)
C9A	0.1691 (10)	0.6700 (7)	1.0428 (8)	0.087 (2)	0.689 (14)
H9A1	0.1289	0.6256	0.9400	0.131*	0.689 (14)
H9A2	0.0664	0.6887	1.0843	0.131*	0.689 (14)
H9A3	0.2542	0.6207	1.1226	0.131*	0.689 (14)
C9B	0.1877 (19)	0.8243 (14)	1.0567 (15)	0.071 (4)	0.311 (14)
H9B1	0.2883	0.8636	1.1337	0.107*	0.311 (14)
H9B2	0.0925	0.8096	1.1096	0.107*	0.311 (14)
H9B3	0.1429	0.8765	0.9617	0.107*	0.311 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.0395 (10)	0.130 (2)	0.0405 (9)	0.0096 (12)	−0.0029 (8)	−0.0003 (11)
N	0.0294 (10)	0.136 (2)	0.0338 (10)	0.0065 (14)	0.0055 (8)	0.0032 (14)
C11	0.0481 (13)	0.0608 (15)	0.0394 (12)	0.0028 (13)	0.0147 (10)	0.0013 (11)
C6	0.0429 (14)	0.0613 (17)	0.0417 (12)	−0.0053 (13)	0.0072 (10)	0.0004 (12)
C10	0.0375 (12)	0.0603 (14)	0.0343 (11)	−0.0002 (12)	0.0038 (9)	−0.0004 (11)
C4	0.0336 (12)	0.0806 (19)	0.0298 (10)	0.0034 (13)	0.0051 (9)	0.0036 (12)
C5	0.0456 (15)	0.0645 (17)	0.0427 (13)	0.0073 (13)	0.0063 (11)	0.0077 (12)
C3	0.0559 (17)	0.0689 (19)	0.0469 (15)	−0.0075 (15)	0.0067 (13)	−0.0085 (13)
C2	0.0631 (18)	0.0565 (17)	0.0542 (15)	0.0061 (14)	0.0040 (14)	0.0069 (13)
C1	0.0417 (15)	0.0677 (18)	0.0404 (12)	0.0050 (13)	0.0003 (11)	0.0069 (12)
C7	0.079 (2)	0.073 (2)	0.083 (3)	−0.0182 (19)	−0.0049 (19)	−0.0069 (18)
C14	0.086 (3)	0.254 (7)	0.0529 (18)	0.027 (4)	0.0323 (19)	0.021 (3)
C13	0.189 (6)	0.118 (4)	0.150 (5)	0.083 (4)	0.126 (5)	0.052 (3)
C12	0.134 (4)	0.178 (5)	0.125 (4)	−0.087 (4)	0.091 (4)	−0.062 (4)
C8A	0.038 (3)	0.075 (5)	0.045 (2)	0.006 (3)	0.0115 (19)	−0.008 (3)
C8B	0.037 (5)	0.083 (10)	0.054 (5)	−0.014 (6)	0.009 (4)	0.001 (5)
C9A	0.066 (4)	0.110 (5)	0.101 (4)	−0.013 (3)	0.049 (3)	0.001 (4)
C9B	0.057 (7)	0.095 (8)	0.073 (7)	0.006 (6)	0.035 (5)	0.003 (6)

Geometric parameters (Å, º) top

O—C10	1.222 (3)	C7—H7C	0.9600
N—C10	1.339 (3)	C14—H14A	0.9600
N—C4	1.439 (3)	C14—H14B	0.9600
N—C8A	1.488 (7)	C14—H14C	0.9600
N—C8B	1.564 (12)	C13—H13A	0.9600
C11—C13	1.486 (5)	C13—H13B	0.9600
C11—C12	1.493 (5)	C13—H13C	0.9600
C11—C14	1.499 (5)	C12—H12A	0.9600
C11—C10	1.525 (3)	C12—H12B	0.9600
C6—C1	1.359 (4)	C12—H12C	0.9600
C6—C5	1.388 (4)	C8A—C9A	1.508 (13)
C6—C7	1.497 (5)	C8A—H8A1	0.9700
C4—C3	1.364 (4)	C8A—H8A2	0.9700
C4—C5	1.370 (4)	C8B—C9B	1.42 (3)
C5—H5	0.9300	C8B—H8B1	0.9700
C3—C2	1.367 (4)	C8B—H8B2	0.9700
C3—H3	0.9300	C9A—H9A1	0.9600
C2—C1	1.370 (4)	C9A—H9A2	0.9600
C2—H2	0.9300	C9A—H9A3	0.9600
C1—H1	0.9300	C9B—H9B1	0.9600
C7—H7A	0.9600	C9B—H9B2	0.9600
C7—H7B	0.9600	C9B—H9B3	0.9600

C10—N—C4	128.83 (19)	H7B—C7—H7C	109.5
C10—N—C8A	117.7 (3)	C11—C14—H14A	109.5
C4—N—C8A	113.3 (2)	C11—C14—H14B	109.5
C10—N—C8B	113.5 (5)	H14A—C14—H14B	109.5
C4—N—C8B	111.7 (4)	C11—C14—H14C	109.5
C13—C11—C12	107.6 (5)	H14A—C14—H14C	109.5
C13—C11—C14	109.0 (4)	H14B—C14—H14C	109.5
C12—C11—C14	108.8 (4)	C11—C13—H13A	109.5
C13—C11—C10	111.7 (3)	C11—C13—H13B	109.5
C12—C11—C10	112.4 (3)	H13A—C13—H13B	109.5
C14—C11—C10	107.3 (2)	C11—C13—H13C	109.5
C1—C6—C5	119.1 (3)	H13A—C13—H13C	109.5
C1—C6—C7	120.8 (3)	H13B—C13—H13C	109.5
C5—C6—C7	120.1 (3)	C11—C12—H12A	109.5
O—C10—N	117.2 (2)	C11—C12—H12B	109.5
O—C10—C11	119.2 (2)	H12A—C12—H12B	109.5
N—C10—C11	123.6 (2)	C11—C12—H12C	109.5
C3—C4—C5	119.1 (2)	H12A—C12—H12C	109.5
C3—C4—N	121.1 (3)	H12B—C12—H12C	109.5
C5—C4—N	119.3 (3)	N—C8A—C9A	106.8 (6)
C4—C5—C6	120.6 (3)	N—C8A—H8A1	110.4
C4—C5—H5	119.7	C9A—C8A—H8A1	110.4
C6—C5—H5	119.7	N—C8A—H8A2	110.4
C4—C3—C2	120.7 (3)	C9A—C8A—H8A2	110.4
C4—C3—H3	119.6	H8A1—C8A—H8A2	108.6
C2—C3—H3	119.6	C9B—C8B—N	100.9 (13)
C3—C2—C1	119.9 (3)	C9B—C8B—H8B1	111.6
C3—C2—H2	120.1	N—C8B—H8B1	111.6
C1—C2—H2	120.1	C9B—C8B—H8B2	111.6
C6—C1—C2	120.6 (2)	N—C8B—H8B2	111.6
C6—C1—H1	119.7	H8B1—C8B—H8B2	109.4
C2—C1—H1	119.7	C8A—C9A—H9A1	109.5
C6—C7—H7A	109.5	C8A—C9A—H9A2	109.5
C6—C7—H7B	109.5	H9A1—C9A—H9A2	109.5
H7A—C7—H7B	109.5	C8A—C9A—H9A3	109.5
C6—C7—H7C	109.5	H9A1—C9A—H9A3	109.5
H7A—C7—H7C	109.5	H9A2—C9A—H9A3	109.5

C4—N—C10—O	175.9 (3)	C8B—N—C4—C5	−109.8 (9)
C8A—N—C10—O	−9.8 (6)	C3—C4—C5—C6	2.2 (4)
C8B—N—C10—O	25.7 (9)	N—C4—C5—C6	174.5 (2)
C4—N—C10—C11	−5.9 (5)	C1—C6—C5—C4	−1.7 (4)
C8A—N—C10—C11	168.3 (5)	C7—C6—C5—C4	179.8 (3)
C8B—N—C10—C11	−156.1 (9)	C5—C4—C3—C2	−1.8 (4)
C13—C11—C10—O	−116.5 (5)	N—C4—C3—C2	−174.0 (3)
C12—C11—C10—O	122.5 (4)	C4—C3—C2—C1	0.9 (5)
C14—C11—C10—O	2.9 (5)	C5—C6—C1—C2	0.8 (4)
C13—C11—C10—N	65.3 (5)	C7—C6—C1—C2	179.3 (3)
C12—C11—C10—N	−55.7 (5)	C3—C2—C1—C6	−0.4 (4)
C14—C11—C10—N	−175.2 (4)	C10—N—C8A—C9A	94.8 (5)
C10—N—C4—C3	−88.2 (4)	C4—N—C8A—C9A	−90.0 (5)
C8A—N—C4—C3	97.3 (5)	C8B—N—C8A—C9A	4.1 (8)
C8B—N—C4—C3	62.4 (9)	C10—N—C8B—C9B	−107.2 (7)
C10—N—C4—C5	99.6 (4)	C4—N—C8B—C9B	97.4 (8)
C8A—N—C4—C5	−74.9 (5)	C8A—N—C8B—C9B	−2.2 (6)

Hydrogen-bond geometry (Å, º) top

Cg is the centoid of the benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Oⁱ	0.93	2.62	3.481 (2)	153
C14—H14A···Cgⁱⁱ	0.96	2.85	3.769 (8)	161

Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

Cg is the centoid of the benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Oⁱ	0.93	2.623	3.481 (2)	153
C14—H14A···Cgⁱⁱ	0.96	2.85	3.769 (8)	161

Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1.

Acknowledgements

The authors acknowledge the IOE X-ray diffractometer facility, University of Mysore, Mysore, for the data collection. BSPM thanks Dr H. C. Devarajegowda, Department of Physics, Yuvarajas College (constituent), University of Mysore, for his support and guidence.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Manojkumar, K. E., Sreenivasa, S., Mohan, N. R., Madhuchakrapani Rao, T. & Harikrishna, T. (2013a). J. Appl. Chem. 2, 730–737. CAS Google Scholar
Manojkumar, K. E., Sreenivasa, S., Shivaraja, G. & Madhuchakrapani Rao, T. (2013b). Molbank, M803, doi:10.3390/M803. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sreenivasa, S., ManojKumar, K. E., Kempaiah, A., Suchetan, P. A. & Palakshamurthy, B. S. (2013). Acta Cryst. E69, o761. CSD CrossRef IUCr Journals Google Scholar

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