Crystal structure of ethyl 2-(3,5-di­fluoro­phen­yl)quinoline-4-carboxyl­ate

Sunitha, V.M.; Naveen, S.; Manjunath, H.R.; Benaka Prasad, S.B.; Manivannan, V.; Lokanath, N.K.

doi:10.1107/S2056989015007677

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 5| May 2015| Pages o341-o342

https://doi.org/10.1107/S2056989015007677

Open

access

Crystal structure of ethyl 2-(3,5-difluorophenyl)quinoline-4-carboxylate

V. M. Sunitha,^a S. Naveen,^b H. R. Manjunath,^c ^* S. B. Benaka Prasad,^d V. Manivannan ^e and N. K. Lokanath ^f

^aDepartment of Physics, Shri Pillappa College of Engineering, Bengaluru 560 089, India, ^bInstitution of Excellence, University of Mysore, Manasagangotri, Mysore 570 006, India, ^cDepartment of Physics, Acharya Institute of Technology, Soldevanahalli, Bengaluru 560 107, India, ^dDepartment of Chemistry, School of Engineering and Technology, Jain University, Bengaluru 562 012, India, ^eDepartment of Physics, Prist University, Vallam, Tanjavur 513 403, India, and ^fDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: manjunathhr@acharya.ac.in

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 17 April 2015; accepted 18 April 2015; online 25 April 2015)

In the title compound, C₁₈H₁₃F₂NO₂, the two rings of the quinoline system are fused almost coaxially, with a dihedral angle between their planes of 2.28 (8)°. The plane of the attached benzene ring is inclined to the plane of the quinoline system by 7.65 (7)°. The carboxylate group attached to the quinoline system is in an antiperiplanar conformation. There is a short intramolecular C—H⋯O contact involving the carbonyl group. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming chains lying in the (1-10) plane.

Keywords: crystal structure; quinoline derivatives; C—H⋯O hydrogen bonds.

CCDC reference: 1060299

1. Related literature

For the crystal structures of related quinoline derivatives, see: Pradeep et al. (2014 ); Shrungesh Kumar et al. (2015 ).

2. Experimental

2.1. Crystal data

C₁₈H₁₃F₂NO₂
M_r = 313.29
Triclinic, $[P \overline 1]$
a = 8.2674 (3) Å
b = 10.0529 (4) Å
c = 10.0562 (4) Å
α = 101.193 (2)°
β = 108.616 (2)°
γ = 98.741 (2)°
V = 756.14 (5) Å³
Z = 2
Cu Kα radiation
μ = 0.90 mm⁻¹
T = 296 K
0.30 × 0.27 × 0.25 mm

2.2. Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.763, T_max = 0.799
9032 measured reflections
2482 independent reflections
2147 reflections with I > 2σ(I)
R_int = 0.038

2.3. Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.131
S = 1.05
2482 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O20	0.93	2.24	2.861 (2)	123
C14—H14⋯O20ⁱ	0.93	2.36	3.275 (2)	167
Symmetry code: (i) x-1, y-1, z.

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; 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.

Supporting information

CCDC reference: 1060299

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015007677/su5120sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007677/su5120Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015007677/su5120Isup3.cml

checkCIF report

Comment top

Quinoline derivatives are well known for their wide range of biological and pharmaceutical activities and are prevalent in pharmacologically active natural and synthetic compounds. Quinoline-4-carboxylates are potential 5HT₃ antagonizer and also they possess anti-emetic activity. In view of their broad spectrum of medicinal properties and in continuation of our work on new quinoline-based therapeutic agents (Pradeep et al., 2014, Shrungesh Kumar et al., 2015), we have synthesized the title compound and report herein on its crystal structure.

The structure of the compound is shown in Fig. 1. The dihedral angle between the benzene ring and the quinoline ring system is 7.65 (7) °. The carboxylate group attached to the quinoline moiety is in an -anti periplanar conformation which is evident by the torsion angle C22—O21—C19—C8 = -176.71 (15)°. The two rings of the quinoline moiety are fused in an axial fashion with a dihedral angle value of 2.28 (8)°. The deviation of the bond length values for C8—C19 and C10—C11 from the standard values can be attributed for the sp³ hybridization.

In the crystal, molecules are linked via C—H···O hydrogen bonds forming chains lying in the (110) plane. (Fig. 2 and Table 1).

Synthesis and crystallization top

To a solution of 2-(3,5-difluorophenyl)quinoline-4-carboxylic acid (0.5 g) in 20 ml of EtOH, 1 ml of H₂SO₄ (conc.) was added. The resulting reaction mixture was refluxed for 15 h. Solvent was removed under reduced pressure and the residue was partitioned between EtOAc and saturated NaHCO₃ solution. The organic layer was washed with water and brine, dried over anhydrous Na₂SO₄, filtered, and condensed to give the title compound as a white solid (yield: 93%). The compound was dissolved in dimethylformamide and the solution was gently heated and left undisturbed. Brown, rectangular crystals grew after 12 days by slow evaporation of the solvent.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. All the H atoms were fixed geometrically (C—H= 0.93–0.96 Å) and allowed to ride on their parent atoms with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms.

Related literature top

For the crystal structures of related quinoline derivatives, see: Pradeep et al. (2014); Shrungesh Kumar et al. (2015).

Structure description top

In the crystal, molecules are linked via C—H···O hydrogen bonds forming chains lying in the (110) plane. (Fig. 2 and Table 1).

For the crystal structures of related quinoline derivatives, see: Pradeep et al. (2014); Shrungesh Kumar et al. (2015).

Synthesis and crystallization top

Refinement details top

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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

Ethyl 2-(3,5-difluorophenyl)quinoline-4-carboxylate top

Crystal data top

C₁₈H₁₃F₂NO₂	Z = 2
M_r = 313.29	F(000) = 324
Triclinic, P1	D_x = 1.376 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.2674 (3) Å	Cell parameters from 2482 reflections
b = 10.0529 (4) Å	θ = 6.1–64.4°
c = 10.0562 (4) Å	µ = 0.90 mm⁻¹
α = 101.193 (2)°	T = 296 K
β = 108.616 (2)°	Rectangle, brown
γ = 98.741 (2)°	0.30 × 0.27 × 0.25 mm
V = 756.14 (5) Å³

Data collection top

Bruker X8 Proteum diffractometer	2482 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2147 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.038
Detector resolution: 10.7 pixels mm^-1	θ_max = 64.4°, θ_min = 6.1°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −11→11
T_min = 0.763, T_max = 0.799	l = −11→11
9032 measured reflections

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0696P)² + 0.099P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2482 reflections	Δρ_max = 0.16 e Å⁻³
210 parameters	Δρ_min = −0.22 e Å⁻³
0 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: 0.011 (3)

Crystal data top

C₁₈H₁₃F₂NO₂	γ = 98.741 (2)°
M_r = 313.29	V = 756.14 (5) Å³
Triclinic, P1	Z = 2
a = 8.2674 (3) Å	Cu Kα radiation
b = 10.0529 (4) Å	µ = 0.90 mm⁻¹
c = 10.0562 (4) Å	T = 296 K
α = 101.193 (2)°	0.30 × 0.27 × 0.25 mm
β = 108.616 (2)°

Data collection top

Bruker X8 Proteum diffractometer	2482 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	2147 reflections with I > 2σ(I)
T_min = 0.763, T_max = 0.799	R_int = 0.038
9032 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.05	Δρ_max = 0.16 e Å⁻³
2482 reflections	Δρ_min = −0.22 e Å⁻³
210 parameters

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 e.s.d.'s 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 > σ(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

	x	y	z	U_iso*/U_eq
F17	−0.07505 (13)	0.11215 (10)	0.69978 (11)	0.0832 (4)
F18	−0.21878 (16)	0.10400 (12)	0.20982 (12)	0.0993 (4)
O20	0.5498 (2)	0.83249 (15)	0.42261 (16)	0.1012 (6)
O21	0.31565 (15)	0.67459 (11)	0.26915 (12)	0.0665 (4)
N1	0.35974 (15)	0.51312 (12)	0.70955 (13)	0.0525 (4)
C2	0.48895 (19)	0.63200 (14)	0.75527 (16)	0.0520 (4)
C3	0.5941 (2)	0.67423 (17)	0.90376 (18)	0.0698 (6)
C4	0.7210 (3)	0.7948 (2)	0.9594 (2)	0.0830 (7)
C5	0.7486 (3)	0.87609 (19)	0.8681 (2)	0.0837 (7)
C6	0.6535 (2)	0.83789 (16)	0.72399 (19)	0.0682 (6)
C7	0.51962 (18)	0.71364 (14)	0.66138 (16)	0.0512 (5)
C8	0.41001 (18)	0.66272 (14)	0.51179 (16)	0.0477 (4)
C9	0.28096 (18)	0.54385 (14)	0.46942 (15)	0.0475 (4)
C10	0.25718 (17)	0.47149 (13)	0.57158 (15)	0.0458 (4)
C11	0.11409 (17)	0.34387 (13)	0.52808 (15)	0.0473 (4)
C12	0.0105 (2)	0.28135 (15)	0.38426 (17)	0.0578 (5)
C13	−0.1193 (2)	0.16400 (16)	0.35114 (17)	0.0622 (5)
C14	−0.1529 (2)	0.10394 (15)	0.45354 (19)	0.0610 (5)
C15	−0.0474 (2)	0.16870 (15)	0.59420 (18)	0.0577 (5)
C16	0.08370 (19)	0.28567 (15)	0.63472 (17)	0.0544 (5)
C19	0.4343 (2)	0.73427 (15)	0.39981 (18)	0.0573 (5)
C22	0.3365 (3)	0.7336 (2)	0.1529 (2)	0.0850 (8)
C23	0.1898 (4)	0.6564 (3)	0.0175 (3)	0.1138 (10)
H3	0.57680	0.61930	0.96470	0.0840*
H4	0.78890	0.82250	1.05790	0.1000*
H5	0.83450	0.95880	0.90700	0.1000*
H6	0.67630	0.89370	0.66540	0.0820*
H9	0.20810	0.51030	0.37230	0.0570*
H12	0.02840	0.31830	0.31080	0.0690*
H14	−0.24150	0.02450	0.42900	0.0730*
H16	0.15150	0.32560	0.73220	0.0650*
H22A	0.44750	0.72490	0.14270	0.1020*
H22B	0.33500	0.83160	0.17440	0.1020*
H23A	0.18670	0.55860	0.00140	0.1710*
H23B	0.20580	0.68790	−0.06260	0.1710*
H23C	0.08140	0.67240	0.02550	0.1710*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F17	0.0858 (7)	0.0796 (7)	0.0865 (7)	−0.0067 (5)	0.0321 (6)	0.0446 (5)
F18	0.1077 (9)	0.0813 (7)	0.0655 (7)	−0.0309 (6)	0.0073 (6)	0.0027 (5)
O20	0.1060 (11)	0.0881 (9)	0.0877 (10)	−0.0363 (8)	0.0244 (8)	0.0372 (7)
O21	0.0731 (7)	0.0690 (7)	0.0589 (7)	0.0017 (5)	0.0253 (6)	0.0284 (5)
N1	0.0544 (7)	0.0478 (7)	0.0520 (7)	0.0038 (5)	0.0171 (6)	0.0154 (5)
C2	0.0507 (8)	0.0465 (7)	0.0545 (8)	0.0059 (6)	0.0162 (7)	0.0122 (6)
C3	0.0755 (11)	0.0633 (10)	0.0568 (9)	0.0024 (8)	0.0119 (8)	0.0151 (7)
C4	0.0820 (12)	0.0736 (11)	0.0620 (11)	−0.0057 (9)	0.0003 (9)	0.0091 (9)
C5	0.0757 (12)	0.0615 (10)	0.0820 (13)	−0.0157 (8)	0.0065 (10)	0.0086 (9)
C6	0.0654 (10)	0.0546 (9)	0.0720 (11)	−0.0056 (7)	0.0173 (8)	0.0156 (8)
C7	0.0478 (8)	0.0445 (7)	0.0587 (9)	0.0066 (6)	0.0186 (7)	0.0118 (6)
C8	0.0463 (7)	0.0436 (7)	0.0572 (8)	0.0086 (6)	0.0225 (6)	0.0168 (6)
C9	0.0464 (7)	0.0455 (7)	0.0497 (8)	0.0064 (6)	0.0166 (6)	0.0145 (6)
C10	0.0452 (7)	0.0428 (7)	0.0503 (8)	0.0082 (6)	0.0178 (6)	0.0145 (6)
C11	0.0454 (7)	0.0431 (7)	0.0547 (8)	0.0080 (6)	0.0187 (6)	0.0163 (6)
C12	0.0628 (9)	0.0505 (8)	0.0564 (9)	0.0002 (7)	0.0208 (7)	0.0169 (7)
C13	0.0615 (9)	0.0513 (8)	0.0595 (9)	−0.0003 (7)	0.0129 (7)	0.0079 (7)
C14	0.0540 (9)	0.0432 (8)	0.0819 (11)	0.0004 (6)	0.0227 (8)	0.0185 (7)
C15	0.0561 (9)	0.0513 (8)	0.0731 (10)	0.0075 (6)	0.0270 (8)	0.0303 (7)
C16	0.0525 (8)	0.0534 (8)	0.0567 (9)	0.0053 (6)	0.0175 (7)	0.0217 (7)
C19	0.0578 (9)	0.0518 (8)	0.0661 (10)	0.0065 (7)	0.0258 (8)	0.0227 (7)
C22	0.0999 (14)	0.0970 (14)	0.0718 (12)	0.0123 (11)	0.0406 (11)	0.0442 (10)
C23	0.1130 (18)	0.156 (2)	0.0710 (13)	0.0141 (16)	0.0238 (12)	0.0552 (14)

Geometric parameters (Å, º) top

F17—C15	1.3611 (19)	C11—C16	1.388 (2)
F18—C13	1.3528 (19)	C12—C13	1.374 (2)
O20—C19	1.194 (2)	C13—C14	1.369 (2)
O21—C19	1.319 (2)	C14—C15	1.367 (2)
O21—C22	1.454 (2)	C15—C16	1.367 (2)
N1—C2	1.366 (2)	C22—C23	1.475 (4)
N1—C10	1.3171 (18)	C3—H3	0.9300
C2—C3	1.407 (2)	C4—H4	0.9300
C2—C7	1.421 (2)	C5—H5	0.9300
C3—C4	1.363 (3)	C6—H6	0.9300
C4—C5	1.390 (3)	C9—H9	0.9300
C5—C6	1.353 (3)	C12—H12	0.9300
C6—C7	1.418 (2)	C14—H14	0.9300
C7—C8	1.427 (2)	C16—H16	0.9300
C8—C9	1.368 (2)	C22—H22A	0.9700
C8—C19	1.497 (2)	C22—H22B	0.9700
C9—C10	1.414 (2)	C23—H23A	0.9600
C10—C11	1.492 (2)	C23—H23B	0.9600
C11—C12	1.383 (2)	C23—H23C	0.9600

C19—O21—C22	115.85 (14)	O20—C19—O21	122.45 (16)
C2—N1—C10	118.74 (12)	O20—C19—C8	124.87 (16)
N1—C2—C3	117.08 (14)	O21—C19—C8	112.65 (14)
N1—C2—C7	123.41 (13)	O21—C22—C23	107.77 (19)
C3—C2—C7	119.51 (14)	C2—C3—H3	120.00
C2—C3—C4	120.79 (16)	C4—C3—H3	120.00
C3—C4—C5	119.67 (17)	C3—C4—H4	120.00
C4—C5—C6	121.59 (19)	C5—C4—H4	120.00
C5—C6—C7	120.72 (16)	C4—C5—H5	119.00
C2—C7—C6	117.68 (14)	C6—C5—H5	119.00
C2—C7—C8	116.27 (13)	C5—C6—H6	120.00
C6—C7—C8	126.04 (14)	C7—C6—H6	120.00
C7—C8—C9	118.95 (13)	C8—C9—H9	120.00
C7—C8—C19	121.86 (13)	C10—C9—H9	120.00
C9—C8—C19	119.19 (13)	C11—C12—H12	120.00
C8—C9—C10	120.74 (13)	C13—C12—H12	120.00
N1—C10—C9	121.83 (13)	C13—C14—H14	122.00
N1—C10—C11	116.69 (12)	C15—C14—H14	122.00
C9—C10—C11	121.48 (12)	C11—C16—H16	121.00
C10—C11—C12	121.97 (13)	C15—C16—H16	121.00
C10—C11—C16	119.24 (13)	O21—C22—H22A	110.00
C12—C11—C16	118.79 (14)	O21—C22—H22B	110.00
C11—C12—C13	119.22 (14)	C23—C22—H22A	110.00
F18—C13—C12	118.35 (14)	C23—C22—H22B	110.00
F18—C13—C14	118.13 (15)	H22A—C22—H22B	108.00
C12—C13—C14	123.52 (15)	C22—C23—H23A	109.00
C13—C14—C15	115.41 (15)	C22—C23—H23B	109.00
F17—C15—C14	117.53 (14)	C22—C23—H23C	110.00
F17—C15—C16	118.38 (14)	H23A—C23—H23B	109.00
C14—C15—C16	124.09 (15)	H23A—C23—H23C	109.00
C11—C16—C15	118.97 (14)	H23B—C23—H23C	109.00

C19—O21—C22—C23	−178.32 (19)	C19—C8—C9—C10	178.34 (14)
C22—O21—C19—O20	1.5 (3)	C9—C8—C19—O21	3.7 (2)
C22—O21—C19—C8	−176.71 (15)	C7—C8—C19—O20	4.4 (3)
C10—N1—C2—C7	−0.3 (2)	C7—C8—C19—O21	−177.37 (14)
C10—N1—C2—C3	179.08 (15)	C9—C8—C19—O20	−174.49 (18)
C2—N1—C10—C9	2.1 (2)	C8—C9—C10—N1	−1.7 (2)
C2—N1—C10—C11	−177.91 (13)	C8—C9—C10—C11	178.32 (14)
N1—C2—C3—C4	−177.18 (18)	N1—C10—C11—C12	−172.73 (14)
C3—C2—C7—C6	−1.9 (2)	C9—C10—C11—C16	−172.80 (14)
C3—C2—C7—C8	178.80 (15)	N1—C10—C11—C16	7.2 (2)
N1—C2—C7—C6	177.45 (15)	C9—C10—C11—C12	7.3 (2)
N1—C2—C7—C8	−1.9 (2)	C16—C11—C12—C13	0.1 (2)
C7—C2—C3—C4	2.2 (3)	C10—C11—C12—C13	−179.96 (16)
C2—C3—C4—C5	−0.9 (3)	C10—C11—C16—C15	−179.93 (15)
C3—C4—C5—C6	−0.7 (4)	C12—C11—C16—C15	0.0 (2)
C4—C5—C6—C7	1.0 (3)	C11—C12—C13—F18	−179.73 (15)
C5—C6—C7—C2	0.3 (3)	C11—C12—C13—C14	−0.1 (3)
C5—C6—C7—C8	179.57 (18)	C12—C13—C14—C15	−0.1 (3)
C6—C7—C8—C9	−177.03 (16)	F18—C13—C14—C15	179.58 (15)
C2—C7—C8—C19	−176.71 (14)	C13—C14—C15—F17	−179.53 (15)
C2—C7—C8—C9	2.2 (2)	C13—C14—C15—C16	0.2 (3)
C6—C7—C8—C19	4.0 (3)	F17—C15—C16—C11	179.57 (14)
C7—C8—C9—C10	−0.6 (2)	C14—C15—C16—C11	−0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O20	0.93	2.24	2.861 (2)	123
C14—H14···O20ⁱ	0.93	2.36	3.275 (2)	167

Symmetry code: (i) x−1, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O20	0.93	2.24	2.861 (2)	123
C14—H14···O20ⁱ	0.93	2.36	3.275 (2)	167

Symmetry code: (i) x−1, y−1, z.

Acknowledgements

The authors are grateful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, Mysuru, for providing access to the single-crystal X-ray diffractometer facility.

References

Bruker (2013). APEX2, SAINT and SADABS. 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
Pradeep, P. S., Naveen, S., Kumara, M. N., Mahadevan, K. M. & Lokanath, N. K. (2014). Acta Cryst. E70, o981–o982. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shrungesh Kumar, T. O., Naveen, S., Kumara, M. N., Mahadevan, K. M. & Lokanath, N. K. (2015). Acta Cryst. E71, o121. CSD CrossRef 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 71| Part 5| May 2015| Pages o341-o342

https://doi.org/10.1107/S2056989015007677

Open

access