(E)-Ethyl 2-(3-cinnamoyl­thio­ureido)acetate

Hassan, I.N.; Yamin, B.M.; Kassim, M.B.

doi:10.1107/S1600536810037918

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2784

https://doi.org/10.1107/S1600536810037918

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(E)-Ethyl 2-(3-cinnamoylthioureido)acetate

Ibrahim N. Hassan,^a Bohari M. Yamin ^a and Mohammad B. Kassim ^a ^*

^aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia
^*Correspondence e-mail: mbkassim@ukm.my

(Received 5 September 2010; accepted 22 September 2010; online 9 October 2010)

In the title compound, C₁₄H₁₆N₂O₃S, the phenyl ring and the ethyl 2-(3-formylthioureido)acetate fragment adopt an E configuration with respect to the C=C bond. An intramolecular N—H⋯O hydrogen bond generating an S(6) ring motif is observed. In the crystal, molecules are linked by N—H⋯S, C—H⋯S and C—H⋯O hydrogen bonds, forming sheets lying parallel to the ab plane.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see: Yamin & Hassan (2004 ); Hassan et al. (2008a ,b ,c , 2009 ); Hung et al. (2010 ). For the synthesis, see: Hassan et al. (2008a).

Experimental

Crystal data

C₁₄H₁₆N₂O₃S
M_r = 292.35
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.1867 (9) Å
b = 9.7417 (16) Å
c = 29.154 (5) Å
V = 1473.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 K
0.49 × 0.38 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.897, T_max = 0.947
10938 measured reflections
3637 independent reflections
2747 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.164
S = 1.03
3637 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1497 Friedel pairs
Flack parameter: −0.04 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1ⁱ	0.86	2.79	3.631 (2)	166
N2—H2A⋯O1	0.86	1.92	2.611 (4)	137
C4—H4A⋯O3ⁱⁱ	0.93	2.54	3.457 (4)	170
C8—H8A⋯S1ⁱ	0.93	2.86	3.716 (3)	153
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) x+2, y+1, z.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810037918/ci5178sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810037918/ci5178Isup2.hkl

checkCIF report

Comment top

The title compound, I, is an ethyl ester derivative of glycine thiourea analogoue to our previously reported molecules, ethyl-2-(3- benzoylthioureido)acetate (II) (Hassan et al., 2008a). As in most carbonylthiourea derivatives of the type R¹C(O)NHC(S)NHR², such as in methyl-2-(3-benzoylthioureido)acetate (Hassan et al., 2009), propyl-2-(3-benzoylthioureido)acetate (Hassan et al., 2008b), butyl-2-(3-benzoylthioureido)acetate (Hassan et al., 2008c) and 1-(2-morpholinoethyl)-3-(3-phenylacryloyl)thiourea (Yamin & Hassan, 2004), the molecule maintains its E—Z configuration with respect to the positions of the cinnamoyl and ethyl acetate groups, respectively, relative to the S atom across the C10—N2 bond (Fig 1). Bond lengths and angles in the molecule are in normal ranges (Allen et al., 1987) and comparable to those observed in (II). However, the C═S bond length [1.675 (3) Å] is slightly longer than that of (II) [1.666 Å]. The cinnamoylthiourea fragment, [S1/O1/N1/N2/C1-C11, A], is essentially planar with a maximum deviation of 0.079 (3) %A, for the atom C1. In the ethyl acetate moeity, [O2/O3/N2/C11-C13, B], the maximum deviation from the mean plane is 0.007 (3) %A for the atom C13. The phenyl ring [C1–C6, C] is inclined to the ethyl acetate mean plane with a dihedral angle of 13.9 (2)° which is larger than that observed in compound (II) [3.6 (1)°]. The additional CH₂ group introduced a more steric geometry to the ethyl acetate moiety. The dihedral angle between the fragments A/B is 10.8 (1)°. There is one intramolecular hydrogen bond, N2—H2A···O1 (Table 1) which resulted in a formation of pseudo-six-membered ring (N2/H2A/O1/C9/N1/C10) (Fig 1). The molecular packing is stablized by N1—H1A···S1, C4—H4A···O3 and C8—H8A···S1 intermolecular hydrogen bonds, which form a sheet parallel to the ab plane.

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Yamin & Hassan (2004); Hassan et al. (2008a,b,c, 2009); Hung et al. (2010). For the preparation, see: Hassan et al. (2008a).

Experimental top

The title compound was synthesized according to a previously reported procedure (Hassan et al., 2008a). Single crystals were obtained by slow evaporation of a CH₂Cl₂ solution at room temperature (yield 71%).

Structure description top

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids shown at the 50% probability level.
	Fig. 2. A packing diagram of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines.

(E)-Ethyl 2-(3-cinnamoylthioureido)acetate top

Crystal data top

C₁₄H₁₆N₂O₃S	F(000) = 616
M_r = 292.35	D_x = 1.318 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2524 reflections
a = 5.1867 (9) Å	θ = 2.2–25.5°
b = 9.7417 (16) Å	µ = 0.23 mm⁻¹
c = 29.154 (5) Å	T = 298 K
V = 1473.1 (4) Å³	Block, colourless
Z = 4	0.49 × 0.38 × 0.24 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3637 independent reflections
Radiation source: fine-focus sealed tube	2747 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scan	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −6→6
T_min = 0.897, T_max = 0.947	k = −12→13
10938 measured reflections	l = −32→38

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)] = 0.063	H-atom parameters constrained
wR(F²) = 0.164	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.036
3637 reflections	Δρ_max = 0.35 e Å⁻³
182 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1497 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (13)

Crystal data top

C₁₄H₁₆N₂O₃S	V = 1473.1 (4) Å³
M_r = 292.35	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.1867 (9) Å	µ = 0.23 mm⁻¹
b = 9.7417 (16) Å	T = 298 K
c = 29.154 (5) Å	0.49 × 0.38 × 0.24 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3637 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2747 reflections with I > 2σ(I)
T_min = 0.897, T_max = 0.947	R_int = 0.033
10938 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.164	Δρ_max = 0.35 e Å⁻³
S = 1.03	Δρ_min = −0.21 e Å⁻³
3637 reflections	Absolute structure: Flack (1983), 1497 Friedel pairs
182 parameters	Absolute structure parameter: −0.04 (13)
0 restraints

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	−0.18635 (18)	0.08578 (8)	0.03548 (2)	0.0573 (2)
O1	0.3380 (5)	0.2635 (3)	0.14456 (7)	0.0694 (7)
O2	0.0044 (6)	−0.0041 (3)	0.20692 (9)	0.0952 (10)
O3	−0.3348 (5)	−0.1415 (2)	0.19707 (7)	0.0712 (7)
N1	0.1857 (5)	0.2377 (2)	0.07184 (7)	0.0446 (5)
H1A	0.2047	0.2655	0.0440	0.053*
N2	−0.0312 (5)	0.0950 (2)	0.12136 (8)	0.0494 (6)
H2A	0.0690	0.1285	0.1420	0.059*
C1	0.9341 (6)	0.5968 (3)	0.05420 (11)	0.0540 (7)
H1B	0.8379	0.5558	0.0310	0.065*
C2	1.1166 (7)	0.6944 (3)	0.04298 (12)	0.0630 (9)
H2B	1.1426	0.7182	0.0124	0.076*
C3	1.2592 (6)	0.7563 (3)	0.07652 (12)	0.0635 (9)
H3A	1.3788	0.8236	0.0689	0.076*
C4	1.2251 (7)	0.7186 (3)	0.12129 (13)	0.0661 (9)
H4A	1.3249	0.7593	0.1441	0.079*
C5	1.0440 (7)	0.6208 (3)	0.13305 (11)	0.0581 (8)
H5A	1.0234	0.5962	0.1637	0.070*
C6	0.8916 (5)	0.5586 (3)	0.09962 (10)	0.0450 (6)
C7	0.7010 (6)	0.4568 (3)	0.11298 (10)	0.0487 (6)
H7A	0.6949	0.4335	0.1439	0.058*
C8	0.5352 (6)	0.3939 (3)	0.08554 (10)	0.0451 (6)
H8A	0.5372	0.4125	0.0543	0.054*
C9	0.3480 (6)	0.2950 (3)	0.10411 (9)	0.0465 (6)
C10	−0.0050 (6)	0.1404 (3)	0.07938 (10)	0.0439 (6)
C11	−0.2162 (6)	−0.0072 (3)	0.13555 (10)	0.0514 (7)
H11A	−0.2033	−0.0869	0.1158	0.062*
H11B	−0.3892	0.0297	0.1328	0.062*
C12	−0.1669 (7)	−0.0482 (3)	0.18390 (11)	0.0604 (8)
C13	−0.3116 (12)	−0.1938 (5)	0.24386 (13)	0.1039 (16)
H13A	−0.1398	−0.2299	0.2490	0.125*
H13B	−0.3433	−0.1210	0.2658	0.125*
C14	−0.5011 (16)	−0.3012 (7)	0.24893 (19)	0.165 (3)
H14A	−0.4645	−0.3534	0.2761	0.247*
H14B	−0.4953	−0.3606	0.2227	0.247*
H14C	−0.6697	−0.2612	0.2514	0.247*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0656 (5)	0.0633 (4)	0.0430 (4)	−0.0139 (4)	−0.0054 (4)	−0.0001 (3)
O1	0.0813 (16)	0.0836 (14)	0.0431 (11)	−0.0360 (15)	−0.0067 (11)	0.0109 (10)
O2	0.105 (2)	0.113 (2)	0.0677 (17)	−0.049 (2)	−0.0235 (16)	0.0243 (17)
O3	0.0789 (16)	0.0854 (15)	0.0494 (12)	−0.0338 (14)	−0.0044 (12)	0.0145 (11)
N1	0.0475 (12)	0.0476 (11)	0.0386 (11)	−0.0068 (12)	0.0019 (11)	0.0020 (9)
N2	0.0518 (14)	0.0541 (13)	0.0422 (12)	−0.0123 (12)	−0.0024 (10)	0.0020 (11)
C1	0.0510 (17)	0.0602 (16)	0.0509 (16)	−0.0087 (15)	−0.0081 (13)	0.0023 (14)
C2	0.063 (2)	0.0684 (18)	0.0579 (19)	−0.0092 (17)	0.0024 (15)	0.0120 (15)
C3	0.053 (2)	0.0544 (16)	0.084 (2)	−0.0068 (15)	0.0053 (16)	−0.0015 (16)
C4	0.059 (2)	0.0655 (19)	0.073 (2)	−0.0121 (16)	−0.0086 (17)	−0.0198 (17)
C5	0.0598 (19)	0.0647 (19)	0.0497 (17)	−0.0059 (17)	−0.0031 (14)	−0.0092 (14)
C6	0.0396 (14)	0.0439 (14)	0.0513 (15)	0.0033 (11)	−0.0010 (12)	−0.0043 (11)
C7	0.0519 (16)	0.0515 (14)	0.0427 (14)	0.0005 (14)	0.0013 (13)	0.0001 (11)
C8	0.0464 (15)	0.0455 (14)	0.0433 (14)	−0.0002 (13)	−0.0003 (12)	0.0017 (11)
C9	0.0473 (16)	0.0472 (14)	0.0449 (14)	−0.0019 (13)	−0.0044 (12)	0.0012 (11)
C10	0.0431 (16)	0.0393 (12)	0.0492 (15)	0.0014 (12)	−0.0004 (12)	−0.0028 (11)
C11	0.0502 (16)	0.0538 (15)	0.0503 (15)	−0.0080 (14)	−0.0016 (13)	0.0065 (12)
C12	0.0631 (19)	0.0642 (18)	0.0538 (17)	−0.0143 (18)	0.0004 (17)	0.0043 (13)
C13	0.124 (4)	0.125 (3)	0.062 (2)	−0.041 (4)	−0.012 (3)	0.038 (2)
C14	0.184 (6)	0.229 (8)	0.083 (3)	−0.108 (6)	−0.038 (4)	0.083 (4)

Geometric parameters (Å, º) top

S1—C10	1.675 (3)	C4—C5	1.381 (5)
O1—C9	1.219 (3)	C4—H4A	0.93
O2—C12	1.193 (4)	C5—C6	1.393 (4)
O3—C12	1.316 (4)	C5—H5A	0.93
O3—C13	1.462 (4)	C6—C7	1.453 (4)
N1—C9	1.380 (4)	C7—C8	1.325 (4)
N1—C10	1.387 (4)	C7—H7A	0.93
N1—H1A	0.86	C8—C9	1.472 (4)
N2—C10	1.308 (4)	C8—H8A	0.93
N2—C11	1.443 (4)	C11—C12	1.487 (4)
N2—H2A	0.86	C11—H11A	0.97
C1—C2	1.381 (4)	C11—H11B	0.97
C1—C6	1.393 (4)	C13—C14	1.443 (7)
C1—H1B	0.93	C13—H13A	0.97
C2—C3	1.366 (5)	C13—H13B	0.97
C2—H2B	0.93	C14—H14A	0.96
C3—C4	1.367 (5)	C14—H14B	0.96
C3—H3A	0.93	C14—H14C	0.96

C12—O3—C13	117.3 (3)	C7—C8—H8A	119.7
C9—N1—C10	127.1 (2)	C9—C8—H8A	119.7
C9—N1—H1A	116.5	O1—C9—N1	122.2 (3)
C10—N1—H1A	116.5	O1—C9—C8	123.2 (3)
C10—N2—C11	124.8 (2)	N1—C9—C8	114.6 (2)
C10—N2—H2A	117.6	N2—C10—N1	117.0 (2)
C11—N2—H2A	117.6	N2—C10—S1	123.3 (2)
C2—C1—C6	121.2 (3)	N1—C10—S1	119.7 (2)
C2—C1—H1B	119.4	N2—C11—C12	110.0 (3)
C6—C1—H1B	119.4	N2—C11—H11A	109.6
C3—C2—C1	120.3 (3)	C12—C11—H11A	109.6
C3—C2—H2B	119.8	N2—C11—H11B	109.7
C1—C2—H2B	119.8	C12—C11—H11B	109.7
C2—C3—C4	119.7 (3)	H11A—C11—H11B	108.2
C2—C3—H3A	120.2	O2—C12—O3	125.3 (3)
C4—C3—H3A	120.2	O2—C12—C11	124.3 (3)
C3—C4—C5	120.6 (3)	O3—C12—C11	110.4 (3)
C3—C4—H4A	119.7	C14—C13—O3	107.0 (4)
C5—C4—H4A	119.7	C14—C13—H13A	110.3
C4—C5—C6	120.8 (3)	O3—C13—H13A	110.3
C4—C5—H5A	119.6	C14—C13—H13B	110.3
C6—C5—H5A	119.6	O3—C13—H13B	110.3
C5—C6—C1	117.3 (3)	H13A—C13—H13B	108.6
C5—C6—C7	119.7 (3)	C13—C14—H14A	109.5
C1—C6—C7	123.0 (3)	C13—C14—H14B	109.5
C8—C7—C6	126.5 (3)	H14A—C14—H14B	109.5
C8—C7—H7A	116.7	C13—C14—H14C	109.5
C6—C7—H7A	116.7	H14A—C14—H14C	109.5
C7—C8—C9	120.6 (3)	H14B—C14—H14C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1ⁱ	0.86	2.79	3.631 (2)	166
N2—H2A···O1	0.86	1.92	2.611 (4)	137
C4—H4A···O3ⁱⁱ	0.93	2.54	3.457 (4)	170
C8—H8A···S1ⁱ	0.93	2.86	3.716 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆N₂O₃S
M_r	292.35
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	5.1867 (9), 9.7417 (16), 29.154 (5)
V (Å³)	1473.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.49 × 0.38 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.897, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	10938, 3637, 2747
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.164, 1.03
No. of reflections	3637
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.21
Absolute structure	Flack (1983), 1497 Friedel pairs
Absolute structure parameter	−0.04 (13)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1ⁱ	0.86	2.79	3.631 (2)	166
N2—H2A···O1	0.86	1.92	2.611 (4)	137
C4—H4A···O3ⁱⁱ	0.93	2.54	3.457 (4)	170
C8—H8A···S1ⁱ	0.93	2.86	3.716 (3)	153

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

Acknowledgements

The authors thank Universiti Kebangsaan Malaysia for providing facilities and grants (UKM-GUP-BTT-07–30-190 and UKM-OUP-TK-16–73/2010) and the Kementerian Pengajian Tinggi, Malaysia, for the research fund No. UKM-ST-06-FRGS0111–2009. The authors also thank Dr J.-C. Daran, CNRS, Tolouse, for his advice.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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