2-Benzyl­sulfanyl-N-(1,3-dimethyl­imidazolidin-2-yl­idene)aniline

Flörke, U.; Neuba, A.; Henkel, G.

doi:10.1107/S1600536813007101

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o554

doi:10.1107/S1600536813007101

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2-Benzylsulfanyl-N-(1,3-dimethylimidazolidin-2-ylidene)aniline

Ulrich Flörke,^a ^* Adam Neuba ^a and Gerald Henkel ^a

^aUniversität Paderborn, Fakultät für Naturwissenschaften, Department Chemie, Warburger Strasse 100, 33098 Paderborn, Germany
^*Correspondence e-mail: ulrich.floerke@upb.de

(Received 8 March 2013; accepted 14 March 2013; online 20 March 2013)

The molecular structure of the title compound, C₁₈H₂₁N₃S, shows a twisted conformation with a dihedral angle of 67.45 (4)° between the aromatic ring planes and an N—C—C—S torsion angle of −5.01 (13)°. The imidazolidine ring and the aniline moiety make a dihedral angle of 56.03 (4)° and the asscociated C—N—C angle is 125.71 (10)°. The guanidine-like C=N double bond is clearly localized, with a bond length of 1.2879 (14) Å. The C—S—C angle is 102.12 (5)° and the S—C(aromatic) and S—C bond lengths are 1.7643 (11) and 1.8159 (12) Å.

Related literature

For a related structure, see: Neuba et al. (2007 ). For the synthesis, see: Herres-Pawlis et al. (2005 ); Lindoy & Livingstone (1968 ).

Experimental

Crystal data

C₁₈H₂₁N₃S
M_r = 311.44
Triclinic, $[P \overline 1]$
a = 7.9814 (5) Å
b = 8.1158 (5) Å
c = 13.9440 (9) Å
α = 97.232 (1)°
β = 102.721 (1)°
γ = 107.915 (1)°
V = 819.89 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 120 K
0.47 × 0.36 × 0.31 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.913, T_max = 0.941
7869 measured reflections
3959 independent reflections
3652 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.095
S = 1.04
3959 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813007101/nk2203sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813007101/nk2203Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813007101/nk2203Isup3.cml

checkCIF report

Related literature top

For a related structure, see: Neuba et al. (2007). For the synthesis, see: Herres-Pawlis et al. (2005); Lindoy & Livingstone (1968).

Experimental top

The title compound was prepared as follows: a solution of N,N,N',N'-dimethylethylenechlorformamidinium chloride (5.07 g, 30 mmol) in dry MeCN was added dropwise to an ice-cooled solution of 2-(benzylthio)aniline (6.45 g, 30 mmol) and triethylamine (4.18 ml, 3.03 g, 30 mmol) in dry MeCN. After 3 h under reflux, a solution of NaOH (1.2 g, 30 mmol) in water was added. The solvents and NEt₃ were then evaporated under vacuum. In order to deprotonate the mono-hydrochloride, 50 wt% KOH (aqueous, 15 ml) was added and the free base was extracted into the MeCN phase (3 x 80 ml). The organic phase was dried with Na₂SO₄. After filtration, the solvent was evaporated under reduced pressure. The title compound was obtained as white powder (yield 60%, 5.6 g). Colourless crystals suitable for X-ray diffraction were obtained by slow cooling of a hot saturated MeCN solution.

Spectroscopic data: ¹H-NMR (500 MHz, CDCl₃, 25°C, δ [p.p.m.]): 2.63 (s, 6H, CH₃), 3.25 (s, 4H, CH₂), 4.11 (s, 2H, CH₂), 6.80 (m, 2H, CH), 7.01 (t, 1H, CH), 7.14 (d, 1H, CH), 7.21 (t, 1H, CH), 7.28 (t, 2H, CH), 7.38 (d, 2H, CH). ¹³C-NMR (125 MHz, CDCl₃, 25°C, δ [p.p.m.]): 34.8 (CH₃), 36.6 (CH₂),48.5 (CH₂) 120.5 (CH), 125.7 (CH), 126.8 (CH), 127.2 (CH), 128.3 (CH), 129.1 (CH), 129.1 (C_quat), 137.9 (C_quat), 148.6 (C_quat), 155.2 (C_gua). IR (KBr, ν [cm^-1]): 3053 (w), 3030 (w),3003 (vw), 2933 (m), 2920 (m), 2868 (m), 2839 (m), 1954 (vw), 1973 (vw), 1635 (versus) (ν (C=N)), 1572 (s) (ν (C=N)),1493 (m), 1469 (m), 1437 (s), 1410 (m), 1394 (m), 1309 (w), 1281 (m), 1236 (m), 1192 (m), 1155 (vw), 1140 (w), 1126 (m),1070 (m), 1032 (s), 1003 (w), 991 (w), 970 (m), 920 (w), 858(w), 845(w), 816 (vw), 783 (m), 764 (m), 735 (s), 717 (s), 698 (m), 648 (m), 596 (w), 586 (w), 571 (w), 545 (w). EI—MS (m/z (%)): 311.2 (100) [M⁺], 278.2 (89), 220.2 (62) [M⁺—CH₂Ph], 202.2 (43), 187.2 (96), 177.2 (40), 165.1 (83), 150.1 (29), 136.0 (52), 126.2 (47), 109.1 (33), 91.1 (55) [CH₂Ph⁺], 70.1 (28), 56.1 (95).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

Fig. 1. Molecular structure of the title compound with anisotropic displacement ellipsoids drawn at the 50% probability level.

2-Benzylsulfanyl-N-(1,3-dimethylimidazolidin-2-ylidene)aniline top

Crystal data top

C₁₈H₂₁N₃S	Z = 2
M_r = 311.44	F(000) = 332
Triclinic, P1	D_x = 1.262 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9814 (5) Å	Cell parameters from 5075 reflections
b = 8.1158 (5) Å	θ = 2.7–28.3°
c = 13.9440 (9) Å	µ = 0.20 mm⁻¹
α = 97.232 (1)°	T = 120 K
β = 102.721 (1)°	Block, colourless
γ = 107.915 (1)°	0.47 × 0.36 × 0.31 mm
V = 819.89 (9) Å³

Data collection top

Bruker SMART APEX diffractometer	3959 independent reflections
Radiation source: sealed tube	3652 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 28.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
T_min = 0.913, T_max = 0.941	k = −10→9
7869 measured reflections	l = −17→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0478P)² + 0.2615P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3959 reflections	Δρ_max = 0.30 e Å⁻³
201 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (3)

Crystal data top

C₁₈H₂₁N₃S	γ = 107.915 (1)°
M_r = 311.44	V = 819.89 (9) Å³
Triclinic, P1	Z = 2
a = 7.9814 (5) Å	Mo Kα radiation
b = 8.1158 (5) Å	µ = 0.20 mm⁻¹
c = 13.9440 (9) Å	T = 120 K
α = 97.232 (1)°	0.47 × 0.36 × 0.31 mm
β = 102.721 (1)°

Data collection top

Bruker SMART APEX diffractometer	3959 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3652 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.941	R_int = 0.016
7869 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.04	Δρ_max = 0.30 e Å⁻³
3959 reflections	Δρ_min = −0.21 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	Occ. (<1)
S1	0.91501 (4)	0.15915 (4)	0.28380 (2)	0.02459 (10)
N1	0.69447 (13)	0.30383 (13)	0.15949 (7)	0.0238 (2)
N2	0.37320 (13)	0.20615 (13)	0.06598 (7)	0.0244 (2)
N3	0.59367 (13)	0.25970 (14)	−0.01322 (7)	0.0264 (2)
C1	0.55992 (15)	0.25990 (14)	0.07961 (8)	0.0215 (2)
C2	0.28581 (18)	0.10816 (18)	0.13298 (10)	0.0338 (3)
H2A	0.2394	−0.0189	0.1035	0.051*	0.50
H2B	0.1839	0.1458	0.1423	0.051*	0.50
H2C	0.3754	0.1317	0.1982	0.051*	0.50
H2D	0.2931	0.1913	0.1925	0.051*	0.50
H2E	0.3485	0.0266	0.1537	0.051*	0.50
H2F	0.1571	0.0407	0.0978	0.051*	0.50
C3	0.28106 (17)	0.14313 (18)	−0.04173 (9)	0.0303 (3)
H3A	0.1700	0.1753	−0.0604	0.036*
H3B	0.2470	0.0132	−0.0619	0.036*
C4	0.42680 (17)	0.24024 (18)	−0.08879 (9)	0.0312 (3)
H4A	0.4179	0.1694	−0.1541	0.037*
H4B	0.4188	0.3567	−0.0983	0.037*
C5	0.76742 (18)	0.37378 (19)	−0.02149 (10)	0.0347 (3)
H5A	0.7645	0.4936	−0.0215	0.052*
H5B	0.7892	0.3277	−0.0843	0.052*
H5C	0.8661	0.3772	0.0357	0.052*
C6	0.68392 (14)	0.34089 (15)	0.25800 (8)	0.0211 (2)
C7	0.59065 (15)	0.44700 (16)	0.29025 (9)	0.0246 (2)
H7A	0.5150	0.4853	0.2420	0.030*
C8	0.60638 (16)	0.49779 (16)	0.39171 (9)	0.0258 (2)
H8A	0.5436	0.5720	0.4124	0.031*
C9	0.71362 (15)	0.44019 (16)	0.46273 (9)	0.0253 (2)
H9A	0.7237	0.4742	0.5321	0.030*
C10	0.80626 (15)	0.33282 (15)	0.43240 (8)	0.0234 (2)
H10A	0.8782	0.2920	0.4811	0.028*
C11	0.79447 (14)	0.28455 (14)	0.33127 (8)	0.0204 (2)
C12	1.00985 (17)	0.08482 (16)	0.39394 (9)	0.0264 (2)
H12A	1.0961	0.1877	0.4467	0.032*
H12B	0.9106	0.0198	0.4214	0.032*
C13	1.10834 (15)	−0.03469 (15)	0.36236 (8)	0.0227 (2)
C14	1.29817 (16)	0.02421 (17)	0.38585 (10)	0.0290 (3)
H14A	1.3675	0.1415	0.4225	0.035*
C15	1.38726 (17)	−0.0870 (2)	0.35612 (11)	0.0347 (3)
H15A	1.5172	−0.0460	0.3728	0.042*
C16	1.28712 (19)	−0.25763 (19)	0.30218 (10)	0.0331 (3)
H16A	1.3484	−0.3334	0.2816	0.040*
C17	1.09805 (19)	−0.31805 (17)	0.27822 (10)	0.0315 (3)
H17A	1.0293	−0.4353	0.2414	0.038*
C18	1.00906 (16)	−0.20683 (16)	0.30818 (9)	0.0273 (2)
H18A	0.8791	−0.2485	0.2916	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03082 (16)	0.02960 (16)	0.01770 (15)	0.01758 (12)	0.00528 (11)	0.00466 (11)
N1	0.0250 (4)	0.0320 (5)	0.0178 (4)	0.0139 (4)	0.0066 (4)	0.0058 (4)
N2	0.0231 (4)	0.0286 (5)	0.0197 (5)	0.0075 (4)	0.0046 (4)	0.0047 (4)
N3	0.0270 (5)	0.0335 (5)	0.0170 (5)	0.0081 (4)	0.0063 (4)	0.0050 (4)
C1	0.0250 (5)	0.0222 (5)	0.0200 (5)	0.0106 (4)	0.0072 (4)	0.0056 (4)
C2	0.0318 (6)	0.0367 (7)	0.0299 (6)	0.0042 (5)	0.0132 (5)	0.0075 (5)
C3	0.0280 (6)	0.0348 (6)	0.0222 (6)	0.0078 (5)	0.0011 (5)	0.0032 (5)
C4	0.0342 (6)	0.0365 (7)	0.0188 (5)	0.0094 (5)	0.0026 (5)	0.0067 (5)
C5	0.0334 (6)	0.0424 (7)	0.0253 (6)	0.0057 (5)	0.0134 (5)	0.0056 (5)
C6	0.0208 (5)	0.0242 (5)	0.0179 (5)	0.0076 (4)	0.0049 (4)	0.0046 (4)
C7	0.0246 (5)	0.0303 (6)	0.0225 (5)	0.0133 (4)	0.0071 (4)	0.0076 (4)
C8	0.0257 (5)	0.0295 (6)	0.0253 (6)	0.0124 (4)	0.0101 (4)	0.0043 (5)
C9	0.0260 (5)	0.0302 (6)	0.0182 (5)	0.0080 (4)	0.0073 (4)	0.0020 (4)
C10	0.0238 (5)	0.0262 (5)	0.0181 (5)	0.0080 (4)	0.0029 (4)	0.0042 (4)
C11	0.0199 (5)	0.0212 (5)	0.0196 (5)	0.0072 (4)	0.0049 (4)	0.0034 (4)
C12	0.0329 (6)	0.0291 (6)	0.0194 (5)	0.0166 (5)	0.0031 (4)	0.0051 (4)
C13	0.0264 (5)	0.0236 (5)	0.0189 (5)	0.0105 (4)	0.0041 (4)	0.0069 (4)
C14	0.0260 (6)	0.0280 (6)	0.0282 (6)	0.0061 (4)	0.0016 (5)	0.0075 (5)
C15	0.0248 (6)	0.0479 (8)	0.0356 (7)	0.0162 (5)	0.0076 (5)	0.0158 (6)
C16	0.0433 (7)	0.0430 (7)	0.0282 (6)	0.0290 (6)	0.0150 (5)	0.0153 (5)
C17	0.0413 (7)	0.0253 (6)	0.0290 (6)	0.0133 (5)	0.0096 (5)	0.0049 (5)
C18	0.0244 (5)	0.0259 (6)	0.0290 (6)	0.0071 (4)	0.0055 (4)	0.0041 (5)

Geometric parameters (Å, º) top

S1—C11	1.7643 (11)	C6—C7	1.3937 (15)
S1—C12	1.8159 (12)	C6—C11	1.4143 (15)
N1—C1	1.2879 (14)	C7—C8	1.3894 (16)
N1—C6	1.3953 (14)	C7—H7A	0.9500
N2—C1	1.3791 (14)	C8—C9	1.3861 (17)
N2—C2	1.4576 (15)	C8—H8A	0.9500
N2—C3	1.4652 (15)	C9—C10	1.3879 (16)
N3—C1	1.3789 (14)	C9—H9A	0.9500
N3—C5	1.4495 (15)	C10—C11	1.3896 (15)
N3—C4	1.4559 (15)	C10—H10A	0.9500
C2—H2A	0.9800	C12—C13	1.5055 (16)
C2—H2B	0.9800	C12—H12A	0.9900
C2—H2C	0.9800	C12—H12B	0.9900
C2—H2D	0.9800	C13—C14	1.3884 (16)
C2—H2E	0.9800	C13—C18	1.3928 (16)
C2—H2F	0.9800	C14—C15	1.3868 (19)
C3—C4	1.5190 (18)	C14—H14A	0.9500
C3—H3A	0.9900	C15—C16	1.383 (2)
C3—H3B	0.9900	C15—H15A	0.9500
C4—H4A	0.9900	C16—C17	1.3823 (19)
C4—H4B	0.9900	C16—H16A	0.9500
C5—H5A	0.9800	C17—C18	1.3870 (17)
C5—H5B	0.9800	C17—H17A	0.9500
C5—H5C	0.9800	C18—H18A	0.9500

C11—S1—C12	102.12 (5)	C7—C6—C11	118.30 (10)
C1—N1—C6	125.71 (10)	N1—C6—C11	116.83 (10)
C1—N2—C2	121.84 (10)	C8—C7—C6	121.15 (10)
C1—N2—C3	108.85 (9)	C8—C7—H7A	119.4
C2—N2—C3	116.19 (10)	C6—C7—H7A	119.4
C1—N3—C5	119.96 (10)	C9—C8—C7	120.01 (11)
C1—N3—C4	109.64 (9)	C9—C8—H8A	120.0
C5—N3—C4	118.80 (10)	C7—C8—H8A	120.0
N1—C1—N3	119.85 (10)	C8—C9—C10	119.91 (11)
N1—C1—N2	131.63 (10)	C8—C9—H9A	120.0
N3—C1—N2	108.52 (9)	C10—C9—H9A	120.0
N2—C2—H2A	109.5	C9—C10—C11	120.45 (10)
N2—C2—H2B	109.5	C9—C10—H10A	119.8
H2A—C2—H2B	109.5	C11—C10—H10A	119.8
N2—C2—H2C	109.5	C10—C11—C6	120.16 (10)
H2A—C2—H2C	109.5	C10—C11—S1	124.81 (9)
H2B—C2—H2C	109.5	C6—C11—S1	115.00 (8)
N2—C2—H2D	109.5	C13—C12—S1	107.83 (8)
N2—C2—H2E	109.5	C13—C12—H12A	110.1
H2D—C2—H2E	109.5	S1—C12—H12A	110.1
N2—C2—H2F	109.5	C13—C12—H12B	110.1
H2D—C2—H2F	109.5	S1—C12—H12B	110.1
H2E—C2—H2F	109.5	H12A—C12—H12B	108.5
N2—C3—C4	102.28 (9)	C14—C13—C18	118.95 (11)
N2—C3—H3A	111.3	C14—C13—C12	120.99 (11)
C4—C3—H3A	111.3	C18—C13—C12	120.06 (10)
N2—C3—H3B	111.3	C15—C14—C13	120.43 (11)
C4—C3—H3B	111.3	C15—C14—H14A	119.8
H3A—C3—H3B	109.2	C13—C14—H14A	119.8
N3—C4—C3	101.32 (9)	C16—C15—C14	120.07 (11)
N3—C4—H4A	111.5	C16—C15—H15A	120.0
C3—C4—H4A	111.5	C14—C15—H15A	120.0
N3—C4—H4B	111.5	C17—C16—C15	120.13 (12)
C3—C4—H4B	111.5	C17—C16—H16A	119.9
H4A—C4—H4B	109.3	C15—C16—H16A	119.9
N3—C5—H5A	109.5	C16—C17—C18	119.76 (12)
N3—C5—H5B	109.5	C16—C17—H17A	120.1
H5A—C5—H5B	109.5	C18—C17—H17A	120.1
N3—C5—H5C	109.5	C17—C18—C13	120.65 (11)
H5A—C5—H5C	109.5	C17—C18—H18A	119.7
H5B—C5—H5C	109.5	C13—C18—H18A	119.7
C7—C6—N1	124.38 (10)

C6—N1—C1—N3	167.61 (10)	C8—C9—C10—C11	0.94 (17)
C6—N1—C1—N2	−13.5 (2)	C9—C10—C11—C6	−1.62 (17)
C5—N3—C1—N1	−26.12 (17)	C9—C10—C11—S1	176.39 (9)
C4—N3—C1—N1	−168.89 (11)	C7—C6—C11—C10	0.90 (16)
C5—N3—C1—N2	154.73 (11)	N1—C6—C11—C10	173.18 (10)
C4—N3—C1—N2	11.97 (13)	C7—C6—C11—S1	−177.30 (8)
C2—N2—C1—N1	−30.72 (19)	N1—C6—C11—S1	−5.01 (13)
C3—N2—C1—N1	−170.28 (12)	C12—S1—C11—C10	10.12 (11)
C2—N2—C1—N3	148.28 (11)	C12—S1—C11—C6	−171.78 (8)
C3—N2—C1—N3	8.73 (13)	C11—S1—C12—C13	176.61 (8)
C1—N2—C3—C4	−24.46 (13)	S1—C12—C13—C14	104.05 (11)
C2—N2—C3—C4	−166.57 (11)	S1—C12—C13—C18	−75.54 (12)
C1—N3—C4—C3	−26.33 (13)	C18—C13—C14—C15	−0.26 (18)
C5—N3—C4—C3	−169.58 (11)	C12—C13—C14—C15	−179.85 (11)
N2—C3—C4—N3	29.57 (12)	C13—C14—C15—C16	0.38 (19)
C1—N1—C6—C7	−45.01 (17)	C14—C15—C16—C17	−0.4 (2)
C1—N1—C6—C11	143.23 (11)	C15—C16—C17—C18	0.22 (19)
N1—C6—C7—C8	−171.15 (11)	C16—C17—C18—C13	−0.10 (19)
C11—C6—C7—C8	0.50 (16)	C14—C13—C18—C17	0.12 (18)
C6—C7—C8—C9	−1.19 (18)	C12—C13—C18—C17	179.71 (11)
C7—C8—C9—C10	0.46 (17)

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁N₃S
M_r	311.44
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	7.9814 (5), 8.1158 (5), 13.9440 (9)
α, β, γ (°)	97.232 (1), 102.721 (1), 107.915 (1)
V (Å³)	819.89 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.47 × 0.36 × 0.31

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.913, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	7869, 3959, 3652
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.095, 1.04
No. of reflections	3959
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXTL (Sheldrick, 2008) and local programs.

Acknowledgements

We thank the German research council (DFG) and the Federal Ministry of education and research (BMBF) for continued support of our work.

References

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