(2E)-1-(4-Chloro­phen­yl)-3-(4-nitro­phen­yl)prop-2-en-1-one

Yamuna, T.S.; Yathirajan, H.S.; Jasinski, J.P.; Keeley, A.C.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536813010854

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 5| May 2013| Pages o790-o791

https://doi.org/10.1107/S1600536813010854

Open

access

(2E)-1-(4-Chlorophenyl)-3-(4-nitrophenyl)prop-2-en-1-one

T. S. Yamuna,^a H. S. Yathirajan,^a Jerry P. Jasinski,^b ^* Amanda C. Keeley,^b B. Narayana ^c and B. K. Sarojini ^d

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^dDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 13 April 2013; accepted 21 April 2013; online 27 April 2013)

In the title compound, C₁₅H₁₀ClNO₃, a substituted chalcone, the dihedral angle between the benzene rings is 5.1 (7)°. The nitro group makes a dihedral angle of 12.5 (3)° with the benzene ring to which it is attached. In the crystal, weak C—H⋯O interactions link the molecules into a one-dimensional array along [010]. The crystal studied was an inversion twin, with a refined ratio for the twin components of 0.6060 (9):0.3939 (1).

Related literature

For the biochemical activity of chalcones, see: Dimmock et al. (1999 ). For different chalcone derivatives, see: Samshuddin et al. (2010 ); Fun et al. (2010a ,b ); Jasinski et al. (2010a ,b ); Baktır et al. (2011a ,b ). For related structures, see: Jing (2009 ); Jasinski et al. (2008 , 2010a,b); Fun et al. (2011 ); Sarojini et al. (2007 ); Ma (2007 ).

Experimental

Crystal data

C₁₅H₁₀ClNO₃
M_r = 287.69
Orthorhombic, P n a 2₁
a = 42.9266 (17) Å
b = 5.9741 (3) Å
c = 5.0680 (2) Å
V = 1299.68 (10) Å³
Z = 4
Cu Kα radiation
μ = 2.67 mm⁻¹
T = 173 K
0.42 × 0.08 × 0.04 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ) T_min = 0.803, T_max = 1.000
12814 measured reflections
2538 independent reflections
2481 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.100
S = 1.14
2538 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2ⁱ	0.93	2.69	3.304 (4)	125
C14—H14⋯O1ⁱⁱ	0.93	2.53	3.219 (4)	131
Symmetry codes: (i) $[-x+1, -y-1, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z-1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813010854/fj2627sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813010854/fj2627Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813010854/fj2627Isup3.cml

checkCIF report

Comment top

Chalcones can be easily obtained from the Claisen-Schmidt reaction of aromatic aldehydes and aromatic ketones. Chalcones have been reported to possess many useful properties including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumour and anticancer activities (Dimmock et al. 1999). The basic skeleton of chalcones which possess α,β-unsaturated carbonyl group is useful synthone for the synthesis of various biodynamic cyclic derivatives such as pyrazoline, benzodiazepine and cyclohexenone derivatives (Samshuddin et al., 2010; Fun et al., 2010a,b; Jasinski et al., 2010a; Baktır et al., 2011a,b). The crystal structures of some of chalcones containing nitro group, viz., (E)-1-(4-nitrophenyl)-3-phenylprop-2-en-1-one (Jing, 2009), (2E)-3-(4-methylphenyl)-1-(3-nitrophenyl)prop-2-en-1-one (Jasinski et al., 2008), (2E)-3-(2-chlorophenyl)-1-(3-nitrophenyl)prop-2-en-1-one (Sarojini et al., 2007); (2E)-1-(2,5-dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one (Fun et al., 2011) and (E)-3-(4-methoxyphenyl)-1-(3-nitrophenyl)prop-2-en-1-one (Ma, 2007) have been reported. In continuation of our work on synthesis of chalcones (Jasinski et al., 2010b) we report here in the crystal structure of the title compound C₁₅H₁₀ClNO₃, (I).

In (I), the dihedral angle between the mean planes of the 4-chlorophenyl and 4-nitrophenyl rings is 5.1 (7)° (Fig. 1). The nitro group makes a dihedral angle of 12.5 (3)° with the plane of the benzene to which it is bonded. In the crystal, weak C—H···N intermolecular interactions are observed and contribute to packing stability (Fig. 2). The crystal studied was an inversion twin, the refined ratio of the twin components being 0.6060 (9):0.3939 (1).

Related literature top

For the biochemical activity of chalcones, see: Dimmock et al. (1999). For different chalcone derivatives, see: Samshuddin et al. (2010); Fun et al. (2010a,b); Jasinski et al. (2010a,b); Baktır et al. (2011a,b). For related structures, see: Jing (2009); Jasinski et al. (2008, 2010a,b); Fun et al. (2011); Sarojini et al. (2007); Ma (2007).

Experimental top

To a mixture of 4-nitrobenzaldehyde (1.51 g, 0.01 mol) and 4-chloroacetophenone (1.54 g, 0.01 mol) in ethanol (50 ml), 10 ml of 10% sodium hydroxide solution was added and stirred at 278-283 K for 3 hours (Fig. 3). The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from acetone by the slow evaporation method (m.p.: 413–418 K).

Structure description top

For the biochemical activity of chalcones, see: Dimmock et al. (1999). For different chalcone derivatives, see: Samshuddin et al. (2010); Fun et al. (2010a,b); Jasinski et al. (2010a,b); Baktır et al. (2011a,b). For related structures, see: Jing (2009); Jasinski et al. (2008, 2010a,b); Fun et al. (2011); Sarojini et al. (2007); Ma (2007).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed along the c axis. Dashed lines indicate weak C—H···O intermolecular interactions. H atoms not involved as weak intermolecular interactions have been deleted for clarity.
	Fig. 3. Reaction scheme.

(2E)-1-(4-Chlorophenyl)-3-(4-nitrophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₀ClNO₃	D_x = 1.470 Mg m⁻³
M_r = 287.69	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, Pna2₁	Cell parameters from 5168 reflections
a = 42.9266 (17) Å	θ = 3.3–32.2°
b = 5.9741 (3) Å	µ = 2.67 mm⁻¹
c = 5.0680 (2) Å	T = 173 K
V = 1299.68 (10) Å³	Rod, colorless
Z = 4	0.42 × 0.08 × 0.04 mm
F(000) = 592

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	2481 reflections with I > 2σ(I)
Detector resolution: 16.1500 pixels mm^-1	R_int = 0.037
ω scans	θ_max = 89.4°, θ_min = 7.5°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −55→55
T_min = 0.803, T_max = 1.000	k = −7→7
12814 measured reflections	l = −4→6
2538 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.0202P)² + 1.4764P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.100	(Δ/σ)_max < 0.001
S = 1.14	Δρ_max = 0.22 e Å⁻³
2538 reflections	Δρ_min = −0.39 e Å⁻³
182 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Absolute structure parameter: 0.39 (3)

Crystal data top

C₁₅H₁₀ClNO₃	V = 1299.68 (10) Å³
M_r = 287.69	Z = 4
Orthorhombic, Pna2₁	Cu Kα radiation
a = 42.9266 (17) Å	µ = 2.67 mm⁻¹
b = 5.9741 (3) Å	T = 173 K
c = 5.0680 (2) Å	0.42 × 0.08 × 0.04 mm

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	2538 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	2481 reflections with I > 2σ(I)
T_min = 0.803, T_max = 1.000	R_int = 0.037
12814 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.100	Δρ_max = 0.22 e Å⁻³
S = 1.14	Δρ_min = −0.39 e Å⁻³
2538 reflections	Absolute structure: Refined as an inversion twin.
182 parameters	Absolute structure parameter: 0.39 (3)
1 restraint

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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.25813 (2)	−0.1905 (2)	1.5999 (3)	0.0500 (3)
O1	0.36902 (7)	−0.7676 (5)	0.9840 (8)	0.0475 (9)
O2	0.49287 (6)	−0.1656 (4)	−0.2914 (6)	0.0318 (6)
O3	0.46280 (6)	0.1223 (4)	−0.2523 (6)	0.0325 (6)
N1	0.47115 (6)	−0.0656 (5)	−0.1880 (6)	0.0233 (6)
C1	0.36318 (8)	−0.5698 (6)	0.9597 (9)	0.0275 (8)
C2	0.33781 (7)	−0.4654 (6)	1.1220 (9)	0.0263 (7)
C3	0.32630 (8)	−0.2524 (6)	1.0729 (9)	0.0326 (9)
H3	0.3351	−0.1653	0.9406	0.039*
C4	0.30164 (9)	−0.1685 (7)	1.2203 (9)	0.0359 (9)
H4	0.2936	−0.0270	1.1850	0.043*
C5	0.28918 (8)	−0.2975 (7)	1.4195 (9)	0.0317 (9)
C6	0.30051 (9)	−0.5094 (7)	1.4746 (9)	0.0340 (9)
H6	0.2918	−0.5950	1.6091	0.041*
C7	0.32480 (8)	−0.5907 (7)	1.3268 (9)	0.0311 (9)
H7	0.3328	−0.7320	1.3639	0.037*
C8	0.38006 (8)	−0.4296 (6)	0.7654 (8)	0.0263 (8)
H8	0.3743	−0.2807	0.7436	0.032*
C9	0.40321 (7)	−0.5122 (6)	0.6217 (9)	0.0258 (7)
H9	0.4088	−0.6602	0.6527	0.031*
C10	0.42078 (7)	−0.3904 (5)	0.4177 (7)	0.0204 (7)
C11	0.44691 (8)	−0.4917 (5)	0.3052 (8)	0.0238 (7)
H11	0.4531	−0.6323	0.3636	0.029*
C12	0.46373 (7)	−0.3858 (5)	0.1074 (8)	0.0220 (7)
H12	0.4811	−0.4538	0.0320	0.026*
C13	0.45406 (7)	−0.1771 (5)	0.0260 (7)	0.0188 (7)
C14	0.42835 (7)	−0.0721 (5)	0.1327 (8)	0.0242 (7)
H14	0.4223	0.0688	0.0737	0.029*
C15	0.41184 (8)	−0.1789 (6)	0.3268 (8)	0.0261 (8)
H15	0.3944	−0.1097	0.3993	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0414 (5)	0.0599 (7)	0.0487 (6)	0.0036 (5)	0.0136 (5)	−0.0095 (7)
O1	0.0412 (15)	0.0303 (14)	0.071 (2)	0.0065 (12)	0.0231 (16)	0.0156 (16)
O2	0.0357 (14)	0.0297 (13)	0.0301 (15)	0.0025 (10)	0.0093 (12)	0.0015 (12)
O3	0.0381 (14)	0.0251 (13)	0.0343 (16)	0.0044 (10)	0.0002 (12)	0.0136 (13)
N1	0.0264 (14)	0.0223 (13)	0.0213 (16)	−0.0014 (11)	−0.0021 (12)	0.0037 (12)
C1	0.0201 (16)	0.0260 (17)	0.036 (2)	−0.0017 (13)	−0.0007 (15)	0.0055 (17)
C2	0.0204 (14)	0.0298 (18)	0.0286 (19)	−0.0037 (12)	−0.0013 (16)	0.0020 (18)
C3	0.0343 (18)	0.032 (2)	0.031 (2)	−0.0026 (15)	0.0078 (18)	0.0044 (19)
C4	0.0338 (19)	0.0298 (18)	0.044 (3)	0.0037 (15)	0.0088 (19)	−0.0001 (19)
C5	0.0233 (16)	0.039 (2)	0.033 (2)	−0.0030 (15)	−0.0001 (16)	−0.0133 (18)
C6	0.0293 (18)	0.043 (2)	0.029 (2)	−0.0116 (17)	0.0002 (17)	0.005 (2)
C7	0.0252 (17)	0.0332 (19)	0.035 (2)	−0.0038 (14)	−0.0031 (16)	0.0070 (18)
C8	0.0228 (16)	0.0266 (17)	0.029 (2)	−0.0004 (13)	0.0001 (15)	0.0043 (17)
C9	0.0240 (15)	0.0263 (16)	0.0271 (19)	−0.0012 (13)	−0.0001 (16)	0.0059 (18)
C10	0.0188 (14)	0.0201 (15)	0.0223 (18)	−0.0006 (12)	−0.0033 (13)	0.0003 (14)
C11	0.0261 (16)	0.0184 (15)	0.027 (2)	0.0011 (12)	−0.0018 (14)	0.0059 (16)
C12	0.0220 (14)	0.0189 (14)	0.0252 (18)	0.0030 (12)	−0.0021 (15)	−0.0006 (16)
C13	0.0206 (14)	0.0187 (14)	0.0172 (17)	−0.0016 (12)	−0.0021 (12)	0.0017 (13)
C14	0.0256 (15)	0.0188 (15)	0.028 (2)	0.0034 (12)	−0.0015 (15)	0.0053 (16)
C15	0.0228 (16)	0.0236 (16)	0.032 (2)	0.0053 (13)	0.0019 (15)	−0.0025 (17)

Geometric parameters (Å, º) top

Cl1—C5	1.738 (4)	C7—H7	0.9300
O1—C1	1.214 (4)	C8—C9	1.327 (5)
O2—N1	1.225 (4)	C8—H8	0.9300
O3—N1	1.222 (4)	C9—C10	1.472 (5)
N1—C13	1.469 (4)	C9—H9	0.9300
C1—C8	1.482 (5)	C10—C11	1.397 (5)
C1—C2	1.501 (5)	C10—C15	1.398 (5)
C2—C3	1.388 (5)	C11—C12	1.388 (5)
C2—C7	1.396 (5)	C11—H11	0.9300
C3—C4	1.389 (5)	C12—C13	1.377 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.378 (6)	C13—C14	1.380 (4)
C4—H4	0.9300	C14—C15	1.370 (5)
C5—C6	1.384 (6)	C14—H14	0.9300
C6—C7	1.372 (6)	C15—H15	0.9300
C6—H6	0.9300

O3—N1—O2	123.8 (3)	C9—C8—C1	121.4 (3)
O3—N1—C13	117.8 (3)	C9—C8—H8	119.3
O2—N1—C13	118.3 (3)	C1—C8—H8	119.3
O1—C1—C8	121.1 (4)	C8—C9—C10	125.8 (3)
O1—C1—C2	119.9 (3)	C8—C9—H9	117.1
C8—C1—C2	119.0 (3)	C10—C9—H9	117.1
C3—C2—C7	118.9 (4)	C11—C10—C15	118.5 (3)
C3—C2—C1	122.7 (4)	C11—C10—C9	119.0 (3)
C7—C2—C1	118.4 (3)	C15—C10—C9	122.5 (3)
C2—C3—C4	120.4 (4)	C12—C11—C10	121.0 (3)
C2—C3—H3	119.8	C12—C11—H11	119.5
C4—C3—H3	119.8	C10—C11—H11	119.5
C5—C4—C3	119.2 (4)	C13—C12—C11	118.2 (3)
C5—C4—H4	120.4	C13—C12—H12	120.9
C3—C4—H4	120.4	C11—C12—H12	120.9
C4—C5—C6	121.5 (4)	C12—C13—C14	122.4 (3)
C4—C5—Cl1	118.5 (3)	C12—C13—N1	118.8 (3)
C6—C5—Cl1	120.0 (3)	C14—C13—N1	118.9 (3)
C7—C6—C5	118.7 (4)	C15—C14—C13	118.9 (3)
C7—C6—H6	120.6	C15—C14—H14	120.5
C5—C6—H6	120.6	C13—C14—H14	120.5
C6—C7—C2	121.3 (4)	C14—C15—C10	121.0 (3)
C6—C7—H7	119.3	C14—C15—H15	119.5
C2—C7—H7	119.3	C10—C15—H15	119.5

O1—C1—C2—C3	−168.6 (4)	C8—C9—C10—C11	172.5 (4)
C8—C1—C2—C3	9.6 (6)	C8—C9—C10—C15	−9.2 (6)
O1—C1—C2—C7	9.9 (6)	C15—C10—C11—C12	0.0 (5)
C8—C1—C2—C7	−172.0 (3)	C9—C10—C11—C12	178.3 (3)
C7—C2—C3—C4	−1.9 (6)	C10—C11—C12—C13	0.4 (5)
C1—C2—C3—C4	176.5 (4)	C11—C12—C13—C14	−0.4 (5)
C2—C3—C4—C5	1.4 (7)	C11—C12—C13—N1	−178.4 (3)
C3—C4—C5—C6	−0.5 (6)	O3—N1—C13—C12	−177.9 (3)
C3—C4—C5—Cl1	−179.5 (3)	O2—N1—C13—C12	2.1 (5)
C4—C5—C6—C7	0.3 (6)	O3—N1—C13—C14	4.1 (5)
Cl1—C5—C6—C7	179.2 (3)	O2—N1—C13—C14	−176.0 (3)
C5—C6—C7—C2	−0.9 (6)	C12—C13—C14—C15	0.1 (5)
C3—C2—C7—C6	1.7 (6)	N1—C13—C14—C15	178.1 (3)
C1—C2—C7—C6	−176.8 (4)	C13—C14—C15—C10	0.3 (6)
O1—C1—C8—C9	−3.7 (6)	C11—C10—C15—C14	−0.3 (5)
C2—C1—C8—C9	178.3 (4)	C9—C10—C15—C14	−178.6 (4)
C1—C8—C9—C10	177.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.93	2.69	3.304 (4)	125
C14—H14···O1ⁱⁱ	0.93	2.53	3.219 (4)	131

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀ClNO₃
M_r	287.69
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	42.9266 (17), 5.9741 (3), 5.0680 (2)
V (Å³)	1299.68 (10)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.67
Crystal size (mm)	0.42 × 0.08 × 0.04

Data collection
Diffractometer	Agilent Xcalibur (Eos, Gemini)
Absorption correction	Multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)
T_min, T_max	0.803, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12814, 2538, 2481
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.100, 1.14
No. of reflections	2538
No. of parameters	182
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.39
Absolute structure	Refined as an inversion twin.
Absolute structure parameter	0.39 (3)

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL2012 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.93	2.69	3.304 (4)	125
C14—H14···O1ⁱⁱ	0.93	2.53	3.219 (4)	131

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

Acknowledgements

TSY thanks the University of Mysore for research facilities. BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England. Google Scholar
Baktır, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o1262–o1263. Web of Science CSD CrossRef IUCr Journals Google Scholar
Baktır, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o1292–o1293. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125–1149. Web of Science PubMed CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fun, H.-K., Chia, T. S., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011). Acta Cryst. E67, o3058–o3059. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010a). Acta Cryst. E66, o582–o583. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010b). Acta Cryst. E66, o864–o865. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Jasinski, J. P., Butcher, R. J., Narayana, B., Lakshmana, K. & Yathirajan, H. S. (2008). Acta Cryst. E64, o1–o2. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Jasinski, J. P., Guild, C. J., Narayana, B., Nayak, P. S. & Yathirajan, H. S. (2010b). Acta Cryst. E66, o1996. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010a). Acta Cryst. E66, o1948–o1949. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Jing, L.-H. (2009). Acta Cryst. E65, o2510. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ma, J.-L. (2007). Acta Cryst. E63, o808–o809. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Samshuddin, S., Narayana, B., Yathirajan, H. S., Safwan, A. P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1279–o1280. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sarojini, B. K., Yathirajan, H. S., Lakshmana, K., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o3211. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar