2-Chloro-N-(4-meth­oxy­benzo­yl)­benzene­sulfonamide

Sreenivasa, S.; Palakshamurthy, B.S.; Pampa, K.J.; Lokanath, N.K.; Suchetan, P.A.

doi:10.1107/S1600536814001482

organic compounds

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Volume 70| Part 2| February 2014| Page o199

doi:10.1107/S1600536814001482

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2-Chloro-N-(4-methoxybenzoyl)benzenesulfonamide

S Sreenivasa,^a B. S. Palakshamurthy,^b K. J. Pampa,^c N. K. Lokanath ^d and P. A. Suchetan ^e ^*

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, ^bDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, ^cDepartment of Studies in Microbiology, University of Mysore, Manasagangotri, Mysore, India, ^dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India, and ^eDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: pasuchetan@yahoo.co.in

(Received 19 January 2014; accepted 21 January 2014; online 25 January 2014)

In the title compound, C₁₄H₁₂ClNO₄S, the dihedral angle between the aromatic rings is 82.07 (1)° and the dihedral angle between the planes defined by the S—N—C=O fragment and the sulfonyl benzene ring is 82.46 (3)°. In the crystal, the molecules are linked into C(4) chains running along [001] by strong N—H⋯O hydrogen bonds. A C—H⋯O interaction reinforces the [001] chains: its graph-set symbol is C(7). The chains are cross-linked into (100) sheets by further C—H⋯O interactions as C(6) chains along [001]. The structure also features weak π–π stacking interactions [centroid–centroid distances = 3.577 (1) and 3.8016 (1) Å].

CCDC reference: 978144

Related literature

For related structures see: Gowda et al. (2010a ,b ); Suchetan et al. (2011a ,b ).

Experimental

Crystal data

C₁₄H₁₂ClNO₄S
M_r = 325.76
Monoclinic, P 2₁ /c
a = 14.5293 (19) Å
b = 10.6225 (14) Å
c = 9.6918 (14) Å
β = 92.695 (5)°
V = 1494.2 (4) Å³
Z = 4
Cu Kα radiation
μ = 3.71 mm⁻¹
T = 293 K
0.44 × 0.35 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.263, T_max = 0.381
17846 measured reflections
2449 independent reflections
2295 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.163
S = 1.11
2449 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.81 (3)	2.09 (3)	2.872 (3)	172 (3)
C3—H3⋯O1ⁱⁱ	0.93	2.57	3.370 (4)	144
C9—H9⋯O2ⁱ	0.93	2.48	3.288 (3)	145
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; 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: 978144

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814001482/hb7189sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814001482/hb7189Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814001482/hb7189Isup3.cml

checkCIF report

Introduction top

As a part of our continued structural studies of N-(aroyl)-arylsulfonamides (Suchetan et al., 2011a, 2011b; Gowda et al., 2010a, 2010b), we report here the crystal structure of the title compound (I) (Fig 1).

Experimental top

Synthesis and crystallization top

The title compound (I) was prepared by refluxing a mixture of 4-methoxybenzoic acid, 2-chlorobenzenesulfonamide and phosphorous oxychloride (POCl₃) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and later dried (Melting point: 445 K).

Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methanolic solution at room temperature.

Refinement top

The H atom of the NH group was located in a difference map and later refined freely. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom).

Results and discussion top

In I, the dihedral angle between the two aromatic rings is 82.07 (1)°. Compared to this, the dihedral angle is 73.3 (1)° in N-(benzoyl)-2-chlorobenzenesulfonamide (II, Gowda et al., 2010a), 85.7 (1)° in N-(4-chlorobenzoyl)-2-chlorobenzenesulfonamide (III, Suchetan et al., 2011a), 89.1 (2)° in N-(4-methylbenzoyl)-2-chlorobenzenesulfonamide (IV, Gowda et al., 2010b) and 85.4 (1)° in N-(4-nitrobenzoyl)-2-chlorobenzenesulfonamide (V, Suchetan et al., 2011b). This shows that introducing a substituent into the para position of the benzoyl ring of II correlates with a increase of the dihedral angle between the aromatic rings. Further, the molecule is twisted at the S atom, the dihedral angle between the planes defined by the S—N—C=O segment in the central chain and the sulfonyl benzene ring being 82.46 (3)°.

In the crystal structure, the molecules are linked into C(4) chains running along [001] through strong N1—H1···O2 hydrogen bonds (Figure 2). The molecules are further linked into one another through C3—H3···O1 (Figure 3) and C9—H9···O2 (Figure 4) interactions into C(6) and C(7) chains running along [001]. The structure is further stabilized by two alternate π-π interactions, Cg(methoxyphenyl)-Cg(methoxyphenyl) and Cg(chlorophenyl)-Cg(chlorophenyl) distances being respectively 3.577 (1)Å and 3.8016 (1)Å.

Related literature top

For related structures see: Gowda et al. (2010a,b); Suchetan et al. (2011a,b).

Structure description top

For related structures see: Gowda et al. (2010a,b); Suchetan et al. (2011a,b).

Synthesis and crystallization top

Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methanolic solution at room temperature.

Refinement details top

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (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.
	Fig. 2. Formation of C(4) chains through N—H···O hydrogen bonds.
	Fig. 3. Formation of C(6) chains through C3—H3···O1 interactions running along [001].
	Fig. 4. Formation of C(7) chains through C9—H9···O2 interactions running along [001].
	Fig. 5. π-π stacking interactions observed in the crystal structure of I.

2-Chloro-N-(4-methoxybenzoyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₂ClNO₄S	Prism
M_r = 325.76	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 445 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 14.5293 (19) Å	Cell parameters from 25 reflections
b = 10.6225 (14) Å	θ = 3.0–64.6°
c = 9.6918 (14) Å	µ = 3.71 mm⁻¹
β = 92.695 (5)°	T = 293 K
V = 1494.2 (4) Å³	Prism, colourless
Z = 4	0.44 × 0.35 × 0.26 mm
F(000) = 672

Data collection top

Bruker APEXII CCD diffractometer	2449 independent reflections
Radiation source: fine-focus sealed tube	2295 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
phi and φ scans	θ_max = 64.6°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
T_min = 0.263, T_max = 0.381	k = −12→12
17846 measured reflections	l = −11→9

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.109P)² + 0.3886P] where P = (F_o² + 2F_c²)/3
2449 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₄H₁₂ClNO₄S	V = 1494.2 (4) Å³
M_r = 325.76	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 14.5293 (19) Å	µ = 3.71 mm⁻¹
b = 10.6225 (14) Å	T = 293 K
c = 9.6918 (14) Å	0.44 × 0.35 × 0.26 mm
β = 92.695 (5)°

Data collection top

Bruker APEXII CCD diffractometer	2449 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2295 reflections with I > 2σ(I)
T_min = 0.263, T_max = 0.381	R_int = 0.058
17846 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.52 e Å⁻³
2449 reflections	Δρ_min = −0.37 e Å⁻³
195 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
H1	0.718 (2)	0.192 (3)	0.295 (4)	0.066 (10)*
S1	0.79503 (4)	0.19067 (5)	0.11546 (6)	0.0448 (3)
Cl1	0.90252 (7)	0.02535 (9)	0.35628 (9)	0.0882 (4)
O1	0.85786 (12)	0.27002 (19)	0.1915 (2)	0.0592 (5)
O2	0.75657 (13)	0.2343 (2)	−0.01265 (19)	0.0645 (5)
O4	0.32115 (14)	0.1078 (2)	0.5017 (3)	0.0826 (7)
C9	0.54708 (16)	0.1902 (2)	0.3736 (3)	0.0497 (6)
H9	0.5956	0.2456	0.3921	0.060*
C8	0.55277 (15)	0.1039 (2)	0.2671 (2)	0.0439 (5)
C7	0.63122 (16)	0.0964 (2)	0.1759 (2)	0.0467 (6)
N1	0.71064 (13)	0.1640 (2)	0.2183 (2)	0.0482 (5)
O3	0.62999 (14)	0.0385 (2)	0.0682 (2)	0.0705 (6)
C10	0.47035 (18)	0.1952 (3)	0.4531 (3)	0.0562 (7)
H10	0.4673	0.2543	0.5235	0.067*
C13	0.47841 (19)	0.0229 (3)	0.2399 (3)	0.0603 (7)
H13	0.4801	−0.0340	0.1671	0.072*
C1	0.84769 (15)	0.0440 (2)	0.0838 (3)	0.0485 (6)
C11	0.39843 (17)	0.1122 (3)	0.4276 (3)	0.0565 (6)
C2	0.89668 (17)	−0.0230 (3)	0.1868 (3)	0.0604 (7)
C12	0.4026 (2)	0.0265 (3)	0.3197 (4)	0.0679 (8)
H12	0.3539	−0.0287	0.3013	0.081*
C3	0.9432 (2)	−0.1334 (3)	0.1497 (5)	0.0842 (12)
H3	0.9776	−0.1787	0.2160	0.101*
C6	0.8439 (2)	0.0008 (3)	−0.0515 (3)	0.0638 (7)
H6	0.8105	0.0453	−0.1195	0.077*
C4	0.9373 (3)	−0.1740 (3)	0.0131 (5)	0.0893 (12)
H4	0.9668	−0.2481	−0.0107	0.107*
C5	0.8897 (3)	−0.1082 (4)	−0.0854 (5)	0.0851 (11)
H5	0.8877	−0.1362	−0.1765	0.102*
C14	0.3152 (3)	0.1932 (4)	0.6139 (5)	0.0940 (13)
H14A	0.3676	0.1823	0.6768	0.141*
H14B	0.2598	0.1771	0.6612	0.141*
H14C	0.3141	0.2780	0.5795	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0411 (4)	0.0523 (4)	0.0410 (4)	0.0020 (2)	0.0010 (3)	0.0046 (2)
Cl1	0.0929 (6)	0.0998 (7)	0.0690 (6)	−0.0016 (5)	−0.0274 (4)	0.0253 (4)
O1	0.0552 (10)	0.0589 (10)	0.0636 (12)	−0.0150 (8)	0.0034 (8)	−0.0062 (8)
O2	0.0623 (11)	0.0852 (13)	0.0459 (10)	0.0168 (10)	0.0013 (8)	0.0179 (9)
O4	0.0488 (11)	0.0906 (16)	0.1105 (19)	−0.0120 (10)	0.0257 (11)	−0.0087 (13)
C9	0.0382 (12)	0.0555 (14)	0.0552 (15)	−0.0069 (9)	−0.0011 (10)	−0.0066 (10)
C8	0.0404 (11)	0.0450 (12)	0.0459 (12)	−0.0027 (9)	−0.0037 (9)	0.0013 (10)
C7	0.0436 (12)	0.0541 (13)	0.0418 (13)	0.0007 (10)	−0.0048 (9)	−0.0023 (10)
N1	0.0421 (10)	0.0628 (12)	0.0394 (12)	−0.0026 (9)	−0.0010 (8)	−0.0064 (10)
O3	0.0594 (11)	0.0961 (15)	0.0557 (12)	−0.0101 (10)	0.0010 (9)	−0.0290 (11)
C10	0.0429 (13)	0.0642 (16)	0.0616 (16)	−0.0030 (10)	0.0047 (11)	−0.0110 (12)
C13	0.0529 (14)	0.0595 (15)	0.0681 (17)	−0.0110 (12)	−0.0015 (12)	−0.0141 (13)
C1	0.0368 (11)	0.0534 (13)	0.0555 (14)	−0.0019 (9)	0.0043 (10)	0.0023 (11)
C11	0.0406 (12)	0.0594 (15)	0.0697 (17)	−0.0029 (11)	0.0055 (11)	0.0053 (13)
C2	0.0396 (12)	0.0604 (16)	0.0806 (19)	−0.0003 (11)	−0.0018 (12)	0.0167 (13)
C12	0.0467 (14)	0.0664 (17)	0.091 (2)	−0.0180 (12)	0.0039 (13)	−0.0085 (15)
C3	0.0488 (15)	0.0647 (19)	0.139 (4)	0.0075 (13)	0.0061 (18)	0.030 (2)
C6	0.0598 (15)	0.0699 (17)	0.0627 (17)	−0.0006 (13)	0.0115 (13)	−0.0087 (14)
C4	0.072 (2)	0.066 (2)	0.133 (4)	0.0070 (16)	0.032 (2)	−0.012 (2)
C5	0.081 (2)	0.077 (2)	0.100 (3)	−0.0035 (18)	0.030 (2)	−0.025 (2)
C14	0.0640 (19)	0.103 (3)	0.119 (3)	0.0030 (18)	0.041 (2)	−0.016 (2)

Geometric parameters (Å, º) top

S1—O2	1.4154 (19)	C13—C12	1.375 (4)
S1—O1	1.4227 (19)	C13—H13	0.9300
S1—N1	1.641 (2)	C1—C6	1.387 (4)
S1—C1	1.769 (3)	C1—C2	1.394 (4)
Cl1—C2	1.720 (3)	C11—C12	1.390 (5)
O4—C11	1.362 (3)	C2—C3	1.408 (5)
O4—C14	1.422 (5)	C12—H12	0.9300
C9—C10	1.385 (4)	C3—C4	1.391 (6)
C9—C8	1.386 (4)	C3—H3	0.9300
C9—H9	0.9300	C6—C5	1.383 (5)
C8—C13	1.396 (3)	C6—H6	0.9300
C8—C7	1.477 (3)	C4—C5	1.348 (6)
C7—O3	1.211 (3)	C4—H4	0.9300
C7—N1	1.404 (3)	C5—H5	0.9300
N1—H1	0.80 (4)	C14—H14A	0.9600
C10—C11	1.381 (4)	C14—H14B	0.9600
C10—H10	0.9300	C14—H14C	0.9600

O2—S1—O1	118.55 (13)	O4—C11—C10	124.3 (3)
O2—S1—N1	108.28 (11)	O4—C11—C12	116.2 (2)
O1—S1—N1	105.51 (11)	C10—C11—C12	119.6 (2)
O2—S1—C1	106.98 (13)	C1—C2—C3	118.5 (3)
O1—S1—C1	109.85 (12)	C1—C2—Cl1	122.2 (2)
N1—S1—C1	107.16 (11)	C3—C2—Cl1	119.3 (3)
C11—O4—C14	117.6 (2)	C13—C12—C11	120.4 (2)
C10—C9—C8	121.2 (2)	C13—C12—H12	119.8
C10—C9—H9	119.4	C11—C12—H12	119.8
C8—C9—H9	119.4	C4—C3—C2	119.5 (3)
C9—C8—C13	118.4 (2)	C4—C3—H3	120.2
C9—C8—C7	123.8 (2)	C2—C3—H3	120.2
C13—C8—C7	117.8 (2)	C5—C6—C1	120.3 (3)
O3—C7—N1	119.4 (2)	C5—C6—H6	119.9
O3—C7—C8	124.2 (2)	C1—C6—H6	119.9
N1—C7—C8	116.4 (2)	C5—C4—C3	121.3 (3)
C7—N1—S1	122.55 (18)	C5—C4—H4	119.4
C7—N1—H1	122 (2)	C3—C4—H4	119.4
S1—N1—H1	115 (2)	C4—C5—C6	120.1 (4)
C11—C10—C9	119.9 (2)	C4—C5—H5	119.9
C11—C10—H10	120.1	C6—C5—H5	119.9
C9—C10—H10	120.1	O4—C14—H14A	109.5
C12—C13—C8	120.6 (3)	O4—C14—H14B	109.5
C12—C13—H13	119.7	H14A—C14—H14B	109.5
C8—C13—H13	119.7	O4—C14—H14C	109.5
C6—C1—C2	120.3 (3)	H14A—C14—H14C	109.5
C6—C1—S1	117.2 (2)	H14B—C14—H14C	109.5
C2—C1—S1	122.4 (2)

C10—C9—C8—C13	1.0 (4)	N1—S1—C1—C2	−67.4 (2)
C10—C9—C8—C7	178.0 (2)	C14—O4—C11—C10	−1.0 (5)
C9—C8—C7—O3	−165.9 (3)	C14—O4—C11—C12	179.3 (3)
C13—C8—C7—O3	11.1 (4)	C9—C10—C11—O4	178.5 (3)
C9—C8—C7—N1	12.8 (3)	C9—C10—C11—C12	−1.8 (4)
C13—C8—C7—N1	−170.2 (2)	C6—C1—C2—C3	1.1 (4)
O3—C7—N1—S1	12.0 (3)	S1—C1—C2—C3	−174.5 (2)
C8—C7—N1—S1	−166.74 (17)	C6—C1—C2—Cl1	−179.3 (2)
O2—S1—N1—C7	47.2 (2)	S1—C1—C2—Cl1	5.1 (3)
O1—S1—N1—C7	175.11 (19)	C8—C13—C12—C11	0.9 (5)
C1—S1—N1—C7	−67.9 (2)	O4—C11—C12—C13	−179.3 (3)
C8—C9—C10—C11	0.8 (4)	C10—C11—C12—C13	0.9 (5)
C9—C8—C13—C12	−1.9 (4)	C1—C2—C3—C4	−1.5 (4)
C7—C8—C13—C12	−179.0 (3)	Cl1—C2—C3—C4	178.9 (3)
O2—S1—C1—C6	0.9 (2)	C2—C1—C6—C5	−0.8 (4)
O1—S1—C1—C6	−129.0 (2)	S1—C1—C6—C5	175.0 (2)
N1—S1—C1—C6	116.9 (2)	C2—C3—C4—C5	1.6 (5)
O2—S1—C1—C2	176.7 (2)	C3—C4—C5—C6	−1.3 (6)
O1—S1—C1—C2	46.8 (2)	C1—C6—C5—C4	0.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.81 (3)	2.09 (3)	2.872 (3)	172 (3)
C3—H3···O1ⁱⁱ	0.93	2.57	3.370 (4)	144
C9—H9···O2ⁱ	0.93	2.48	3.288 (3)	145

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.81 (3)	2.09 (3)	2.872 (3)	172 (3)
C3—H3···O1ⁱⁱ	0.93	2.57	3.370 (4)	144
C9—H9···O2ⁱ	0.93	2.48	3.288 (3)	145

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

Acknowledgements

The authors acknowledge the IOE X-ray diffractometer facility, University of Mysore, Mysore, for the data collection.

References

Bruker (2009). APEX2, SADABS, and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010a). Acta Cryst. E66, o794. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010b). Acta Cryst. E66, o1466. Web of Science CSD CrossRef IUCr Journals 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suchetan, P. A., Foro, S. & Gowda, B. T. (2011a). Acta Cryst. E67, o146. Web of Science CSD CrossRef IUCr Journals Google Scholar
Suchetan, P. A., Foro, S. & Gowda, B. T. (2011b). Acta Cryst. E67, o930. Web of Science CSD CrossRef IUCr Journals Google Scholar

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