1-(3-Chloro­benzo­yl)-3-(2,3-dimethyl­phen­yl)thio­urea

Khawar Rauf, M.; Bolte, M.; Badshah, A.

doi:10.1107/S1600536809000063

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o240

doi:10.1107/S1600536809000063

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1-(3-Chlorobenzoyl)-3-(2,3-dimethylphenyl)thiourea

M. Khawar Rauf,^a Michael Bolte ^b and Amin Badshah ^a ^*

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: aminbadshah@yahoo.com

(Received 3 December 2008; accepted 1 January 2009; online 8 January 2009)

The title molecule, C₁₆H₁₅ClN₂OS, exists in the solid state in its thione form with typical thiourea C—S and C—O bonds lengths, as well as shortened C—N bonds. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation and intermolecular N—H⋯S hydrogen bonds link the molecules into centrosymmetric dimers. The dihedral angle between the aromatic rings is 50.18 (5)°.

Related literature

For related compounds, see: Khawar Rauf et al. (2006a ,b ,c ,d ). For reference bond-length data, see: Allen (2002 ).

Experimental

Crystal data

C₁₆H₁₅ClN₂OS
M_r = 318.81
Triclinic, $[P \overline 1]$
a = 8.1315 (9) Å
b = 9.3906 (12) Å
c = 10.5310 (12) Å
α = 93.296 (8)°
β = 92.623 (8)°
γ = 102.579 (9)°
V = 782.14 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 173 (2) K
0.46 × 0.42 × 0.41 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003 ; Blessing, 1995 ) T_min = 0.846, T_max = 0.861
8257 measured reflections
3066 independent reflections
2846 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.04
3066 reflections
201 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86 (2)	1.99 (2)	2.6840 (16)	137.7 (17)
N1—H1⋯S1ⁱ	0.836 (19)	2.636 (19)	3.4376 (13)	161.2 (15)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000063/bv2114sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000063/bv2114Isup2.hkl

checkCIF report

Comment top

The background to this study has been set out in our previous work on the structural chemistry of N,N'-disubstituted thioureas (Khawar Rauf et al., 2006a,b,c,d). Herein, as a continuation of these studies, the structure of the title compound (I) is described. A depiction of the molecule is given in Fig. 1. Bond lengths and angles, see the table of selected geometric parameters, can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002; Khawar Rauf et al., 2006a).The molecule exists in the thione form with typical thiourea C—S and C—O bonds, as well as shortened C—N bond lengths. The thiocarbonyl and carbonyl groups are almost coplanar. The dihedral angle between the aromatic rings is 50.18 (5)°. An intramolecular N—H···O hydrogen bond is present (Table 2), forming a six-membered ring commonly observed in this class of compounds (Khawar Rauf et al., 2006d). Intermolecular N—H···S hydrogen bonds link the molecules to form centrosymmetric dimers.

Related literature top

For related compounds, see: Khawar Rauf et al. (2006a,b,c,d). For standard bond-length data, see: Allen (2002)

Experimental top

Freshly prepared 3-chlorobenzoyl isothiocyanate (2.0 g, 10 mmol) was stirred in acetone (40 ml) for 20 min. Neat 2,3-dimethylaniline (1.62 g, 10 mmol) was then added and the resulting mixture was stirred for 1.5 h. The reaction mixture was then poured into acidified (pH 4) water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol–1,1-dichloromethane (1:10 v/v) to give fine crystals of (I), with an overall yield of 90%. Full spectroscopic and physical characterization will be reported elsewhere.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I) showing atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram. Hydrogen bonds are shown as dashed lines.

1-(3-chlorobenzoyl)-3-(2,3-dimethylphenyl)thiourea top

Crystal data top

C₁₆H₁₅ClN₂OS	Z = 2
M_r = 318.81	F(000) = 332
Triclinic, P1	D_x = 1.354 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1315 (9) Å	Cell parameters from 7706 reflections
b = 9.3906 (12) Å	θ = 3.7–26.1°
c = 10.5310 (12) Å	µ = 0.38 mm⁻¹
α = 93.296 (8)°	T = 173 K
β = 92.623 (8)°	Block, colourless
γ = 102.579 (9)°	0.46 × 0.42 × 0.41 mm
V = 782.14 (16) Å³

Data collection top

Stoe IPDS II two-circle diffractometer	3066 independent reflections
Radiation source: fine-focus sealed tube	2846 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 26.1°, θ_min = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −10→10
T_min = 0.846, T_max = 0.861	k = −10→11
8257 measured reflections	l = −12→12

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.041P)² + 0.3782P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3066 reflections	Δρ_max = 0.27 e Å⁻³
201 parameters	Δρ_min = −0.33 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: 0.097 (5)

Crystal data top

C₁₆H₁₅ClN₂OS	γ = 102.579 (9)°
M_r = 318.81	V = 782.14 (16) Å³
Triclinic, P1	Z = 2
a = 8.1315 (9) Å	Mo Kα radiation
b = 9.3906 (12) Å	µ = 0.38 mm⁻¹
c = 10.5310 (12) Å	T = 173 K
α = 93.296 (8)°	0.46 × 0.42 × 0.41 mm
β = 92.623 (8)°

Data collection top

Stoe IPDS II two-circle diffractometer	3066 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	2846 reflections with I > 2σ(I)
T_min = 0.846, T_max = 0.861	R_int = 0.037
8257 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.27 e Å⁻³
3066 reflections	Δρ_min = −0.33 e Å⁻³
201 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
S1	0.23509 (5)	0.60717 (4)	0.59551 (4)	0.02881 (14)
Cl1	−0.24623 (5)	−0.05881 (5)	0.30214 (4)	0.03438 (14)
O1	−0.01441 (13)	0.25159 (11)	0.84778 (9)	0.0258 (2)
N1	0.03004 (15)	0.36655 (13)	0.66166 (11)	0.0201 (3)
H1	−0.014 (2)	0.3701 (19)	0.5889 (18)	0.025 (4)*
N2	0.24161 (15)	0.47809 (13)	0.81460 (11)	0.0215 (3)
H2	0.192 (2)	0.412 (2)	0.8612 (19)	0.034 (5)*
C1	−0.04406 (17)	0.25179 (15)	0.73206 (13)	0.0192 (3)
C2	0.16893 (17)	0.48027 (14)	0.69839 (13)	0.0190 (3)
C11	−0.16148 (16)	0.12650 (14)	0.65810 (13)	0.0190 (3)
C12	−0.15027 (17)	0.09819 (15)	0.52694 (13)	0.0203 (3)
H12	−0.0703	0.1612	0.4809	0.024*
C13	−0.25894 (18)	−0.02426 (15)	0.46557 (14)	0.0232 (3)
C14	−0.37636 (19)	−0.11864 (16)	0.53128 (16)	0.0280 (3)
H14	−0.4495	−0.2015	0.4877	0.034*
C15	−0.38527 (18)	−0.09009 (16)	0.66142 (16)	0.0280 (3)
H15	−0.4650	−0.1538	0.7071	0.034*
C16	−0.27787 (18)	0.03152 (16)	0.72518 (14)	0.0238 (3)
H16	−0.2837	0.0499	0.8143	0.029*
C21	0.39206 (17)	0.58278 (15)	0.86417 (13)	0.0194 (3)
C22	0.55031 (18)	0.56849 (15)	0.82648 (13)	0.0213 (3)
C23	0.69413 (18)	0.67134 (16)	0.88045 (14)	0.0240 (3)
C24	0.67324 (19)	0.78059 (16)	0.96980 (14)	0.0255 (3)
H24	0.7701	0.8486	1.0066	0.031*
C25	0.5146 (2)	0.79247 (17)	1.00630 (14)	0.0280 (3)
H25	0.5034	0.8679	1.0671	0.034*
C26	0.37181 (18)	0.69272 (16)	0.95296 (14)	0.0243 (3)
H26	0.2624	0.6996	0.9768	0.029*
C27	0.5701 (2)	0.44874 (18)	0.73006 (16)	0.0325 (4)
H27A	0.4650	0.3736	0.7199	0.049*
H27B	0.6625	0.4049	0.7598	0.049*
H27C	0.5956	0.4901	0.6480	0.049*
C28	0.8687 (2)	0.6643 (2)	0.84115 (18)	0.0412 (4)
H28A	0.9513	0.7479	0.8823	0.062*
H28B	0.8720	0.6671	0.7484	0.062*
H28C	0.8961	0.5732	0.8672	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0257 (2)	0.0279 (2)	0.0257 (2)	−0.00979 (15)	−0.00909 (14)	0.01144 (15)
Cl1	0.0333 (2)	0.0398 (2)	0.0276 (2)	0.00868 (17)	−0.00649 (16)	−0.01303 (16)
O1	0.0274 (5)	0.0271 (5)	0.0184 (5)	−0.0040 (4)	−0.0013 (4)	0.0031 (4)
N1	0.0201 (6)	0.0193 (6)	0.0172 (6)	−0.0028 (4)	−0.0054 (5)	0.0021 (4)
N2	0.0202 (6)	0.0212 (6)	0.0188 (6)	−0.0040 (5)	−0.0040 (5)	0.0030 (5)
C1	0.0175 (6)	0.0190 (6)	0.0199 (7)	0.0015 (5)	0.0001 (5)	0.0016 (5)
C2	0.0171 (6)	0.0180 (6)	0.0201 (7)	0.0008 (5)	−0.0019 (5)	0.0007 (5)
C11	0.0159 (6)	0.0166 (6)	0.0234 (7)	0.0020 (5)	−0.0026 (5)	0.0019 (5)
C12	0.0179 (6)	0.0182 (6)	0.0238 (7)	0.0026 (5)	−0.0021 (5)	0.0008 (5)
C13	0.0227 (7)	0.0216 (7)	0.0253 (7)	0.0078 (5)	−0.0061 (6)	−0.0046 (6)
C14	0.0222 (7)	0.0184 (7)	0.0395 (9)	−0.0007 (5)	−0.0090 (6)	−0.0025 (6)
C15	0.0215 (7)	0.0211 (7)	0.0384 (9)	−0.0023 (6)	−0.0023 (6)	0.0078 (6)
C16	0.0215 (7)	0.0226 (7)	0.0255 (7)	0.0009 (5)	−0.0006 (6)	0.0046 (6)
C21	0.0206 (7)	0.0189 (6)	0.0163 (6)	0.0002 (5)	−0.0050 (5)	0.0023 (5)
C22	0.0236 (7)	0.0211 (7)	0.0184 (7)	0.0041 (5)	−0.0029 (5)	0.0011 (5)
C23	0.0204 (7)	0.0285 (7)	0.0220 (7)	0.0032 (6)	−0.0033 (5)	0.0038 (6)
C24	0.0235 (7)	0.0249 (7)	0.0240 (7)	−0.0014 (6)	−0.0084 (6)	0.0014 (6)
C25	0.0321 (8)	0.0252 (7)	0.0245 (7)	0.0056 (6)	−0.0055 (6)	−0.0073 (6)
C26	0.0206 (7)	0.0286 (7)	0.0229 (7)	0.0053 (6)	−0.0018 (5)	−0.0021 (6)
C27	0.0316 (8)	0.0343 (8)	0.0311 (8)	0.0092 (7)	0.0010 (6)	−0.0083 (7)
C28	0.0225 (8)	0.0568 (11)	0.0410 (10)	0.0047 (7)	−0.0002 (7)	−0.0057 (8)

Geometric parameters (Å, º) top

S1—C2	1.6751 (14)	C16—H16	0.9500
Cl1—C13	1.7450 (15)	C21—C26	1.394 (2)
O1—C1	1.2315 (17)	C21—C22	1.395 (2)
N1—C1	1.3871 (18)	C22—C23	1.417 (2)
N1—C2	1.3974 (17)	C22—C27	1.511 (2)
N1—H1	0.836 (19)	C23—C24	1.395 (2)
N2—C2	1.3377 (18)	C23—C28	1.511 (2)
N2—C21	1.4472 (17)	C24—C25	1.388 (2)
N2—H2	0.86 (2)	C24—H24	0.9500
C1—C11	1.4966 (18)	C25—C26	1.395 (2)
C11—C16	1.3986 (19)	C25—H25	0.9500
C11—C12	1.402 (2)	C26—H26	0.9500
C12—C13	1.3930 (19)	C27—H27A	0.9800
C12—H12	0.9500	C27—H27B	0.9800
C13—C14	1.392 (2)	C27—H27C	0.9800
C14—C15	1.390 (2)	C28—H28A	0.9800
C14—H14	0.9500	C28—H28B	0.9800
C15—C16	1.393 (2)	C28—H28C	0.9800
C15—H15	0.9500

C1—N1—C2	127.82 (12)	C26—C21—C22	122.41 (13)
C1—N1—H1	117.0 (12)	C26—C21—N2	117.43 (13)
C2—N1—H1	115.2 (12)	C22—C21—N2	120.12 (12)
C2—N2—C21	123.54 (12)	C21—C22—C23	117.98 (13)
C2—N2—H2	116.1 (13)	C21—C22—C27	121.75 (13)
C21—N2—H2	120.3 (13)	C23—C22—C27	120.27 (13)
O1—C1—N1	122.49 (12)	C24—C23—C22	119.38 (13)
O1—C1—C11	121.81 (12)	C24—C23—C28	120.03 (14)
N1—C1—C11	115.70 (12)	C22—C23—C28	120.59 (14)
N2—C2—N1	116.65 (12)	C25—C24—C23	121.69 (13)
N2—C2—S1	124.50 (10)	C25—C24—H24	119.2
N1—C2—S1	118.84 (10)	C23—C24—H24	119.2
C16—C11—C12	120.14 (12)	C24—C25—C26	119.50 (14)
C16—C11—C1	117.91 (12)	C24—C25—H25	120.2
C12—C11—C1	121.84 (12)	C26—C25—H25	120.2
C13—C12—C11	118.60 (13)	C21—C26—C25	119.04 (13)
C13—C12—H12	120.7	C21—C26—H26	120.5
C11—C12—H12	120.7	C25—C26—H26	120.5
C14—C13—C12	121.68 (14)	C22—C27—H27A	109.5
C14—C13—Cl1	119.67 (11)	C22—C27—H27B	109.5
C12—C13—Cl1	118.64 (12)	H27A—C27—H27B	109.5
C15—C14—C13	119.17 (13)	C22—C27—H27C	109.5
C15—C14—H14	120.4	H27A—C27—H27C	109.5
C13—C14—H14	120.4	H27B—C27—H27C	109.5
C14—C15—C16	120.31 (14)	C23—C28—H28A	109.5
C14—C15—H15	119.8	C23—C28—H28B	109.5
C16—C15—H15	119.8	H28A—C28—H28B	109.5
C15—C16—C11	120.08 (14)	C23—C28—H28C	109.5
C15—C16—H16	120.0	H28A—C28—H28C	109.5
C11—C16—H16	120.0	H28B—C28—H28C	109.5

C2—N1—C1—O1	14.4 (2)	C12—C11—C16—C15	−1.2 (2)
C2—N1—C1—C11	−164.92 (13)	C1—C11—C16—C15	−177.41 (13)
C21—N2—C2—N1	176.32 (12)	C2—N2—C21—C26	103.83 (16)
C21—N2—C2—S1	−2.7 (2)	C2—N2—C21—C22	−78.45 (18)
C1—N1—C2—N2	1.0 (2)	C26—C21—C22—C23	−0.6 (2)
C1—N1—C2—S1	−179.91 (11)	N2—C21—C22—C23	−178.24 (12)
O1—C1—C11—C16	20.3 (2)	C26—C21—C22—C27	−179.96 (14)
N1—C1—C11—C16	−160.43 (12)	N2—C21—C22—C27	2.4 (2)
O1—C1—C11—C12	−155.86 (13)	C21—C22—C23—C24	1.0 (2)
N1—C1—C11—C12	23.43 (19)	C27—C22—C23—C24	−179.67 (14)
C16—C11—C12—C13	1.1 (2)	C21—C22—C23—C28	−178.42 (14)
C1—C11—C12—C13	177.14 (12)	C27—C22—C23—C28	0.9 (2)
C11—C12—C13—C14	−0.5 (2)	C22—C23—C24—C25	−0.8 (2)
C11—C12—C13—Cl1	179.51 (10)	C28—C23—C24—C25	178.63 (15)
C12—C13—C14—C15	−0.1 (2)	C23—C24—C25—C26	0.2 (2)
Cl1—C13—C14—C15	179.96 (11)	C22—C21—C26—C25	0.0 (2)
C13—C14—C15—C16	0.0 (2)	N2—C21—C26—C25	177.71 (13)
C14—C15—C16—C11	0.7 (2)	C24—C25—C26—C21	0.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86 (2)	1.99 (2)	2.6840 (16)	137.7 (17)
N1—H1···S1ⁱ	0.836 (19)	2.636 (19)	3.4376 (13)	161.2 (15)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅ClN₂OS
M_r	318.81
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.1315 (9), 9.3906 (12), 10.5310 (12)
α, β, γ (°)	93.296 (8), 92.623 (8), 102.579 (9)
V (Å³)	782.14 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.46 × 0.42 × 0.41

Data collection
Diffractometer	Stoe IPDS II two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.846, 0.861
No. of measured, independent and observed [I > 2σ(I)] reflections	8257, 3066, 2846
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.085, 1.04
No. of reflections	3066
No. of parameters	201
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.33

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86 (2)	1.99 (2)	2.6840 (16)	137.7 (17)
N1—H1···S1ⁱ	0.836 (19)	2.636 (19)	3.4376 (13)	161.2 (15)

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

MKR is grateful to the HEC, Pakistan, for financial support for a PhD programme under scholarship No. ILC-0363104.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Khawar Rauf, M., Badshah, A. & Bolte, M. (2006a). Acta Cryst. E62, o1859–o1860. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khawar Rauf, M., Badshah, A. & Bolte, M. (2006b). Acta Cryst. E62, o2221–o2222. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khawar Rauf, M., Badshah, A. & Bolte, M. (2006c). Acta Cryst. E62, o2444–o2445. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khawar Rauf, M., Badshah, A., Bolte, M. & Zaeem Akhtar, M. (2006d). Acta Cryst. E62, o1849–o1850. 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
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar