rac-3-[(3-Chloro­anilino)(4-chloro­phenyl)meth­yl]thian-4-one

Harms, K.; Abaee, M.S.; Mojtahedi, M.M.; Mesbah, A.W.

doi:10.1107/S1600536812004680

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o646

doi:10.1107/S1600536812004680

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rac-3-[(3-Chloroanilino)(4-chlorophenyl)methyl]thian-4-one

Klaus Harms,^a ^* M. Saeed Abaee,^b Mohammad M. Mojtahedi ^b and A. Wahid Mesbah ^b

^aFachbereich Chemie, Philipps Universität Marburg, Hans Meerwein Str., Marburg D-35032, Germany, and ^bDepartment of Organic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, PO Box 14335-186, Tehran, Iran
^*Correspondence e-mail: harms@chemie.uni-marburg.de

(Received 17 January 2012; accepted 3 February 2012; online 10 February 2012)

In the title compound, C₁₈H₁₇Cl₂NOS, the thiopyranone ring adopts a chair conformation, with the substituent in the axial position. The dihedral angle between the two benzene rings is 89.43 (1)°. In the crystal, molecules form inversion dimers through intermolecular N—H⋯O hydrogen bonds [graph set R₂²(8)].

Related literature

For the preparation and spectroscopic characterization of a series of related compounds and the crystal structure of 3-[(phenylamino)(p-tolyl)methly]dihydro-2H-thiopyran-4(3H)-one, see: Abaee et al. (2012 ). For the crystal structures of related compounds, see: Guo et al. (2007 ); Fun et al. (2009 ); Harms et al. (2012 ). For patterns in hydrogen bonding, see: Bernstein et al. (1995 ). For defining the relative configuration of diastereomers, see: IUPAC (2012 ).

Experimental

Crystal data

C₁₈H₁₇Cl₂NOS
M_r = 366.29
Monoclinic, P 2₁ /c
a = 11.2611 (8) Å
b = 8.6686 (7) Å
c = 18.0976 (12) Å
β = 105.266 (8)°
V = 1704.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 193 K
0.29 × 0.24 × 0.05 mm

Data collection

Stoe IPDS-1 image-plate diffractometer
Absorption correction: integration X-RED32 (Stoe & Cie, 2006 ) T_min = 0.890, T_max = 0.978
15404 measured reflections
3134 independent reflections
1867 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.048
S = 0.64
3134 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯O1ⁱ	0.81 (2)	2.27 (2)	3.070 (2)	168 (2)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: EXPOSE (Stoe & Cie, 1994 ); cell refinement: CELL (Stoe & Cie, 1994); data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg, 2007 ); software used to prepare material for publication: publCIF (Westrip, 2010 ), PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812004680/zs2176sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004680/zs2176Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812004680/zs2176Isup3.cml

checkCIF report

Comment top

The title compound is an example of a product from an anti-selective three-component Mannich reaction involving the thiopyran-4-one system (Abaee et al., 2012). The same anti configuration has been found recently in the crystal structures of two other compounds of this series (Abaee et al., 2012; Harms et al., 2012). In the title compund the thiopyranone ring adopts a chair-like conformation with the substituent in the axial position. The relative configuration of the stereogenic centres at C3 and C7 is R*, S* (IUPAC, 1997). The dihedral angle between the two benzene rings in the molecule is 89.43 (10)°. In the crystal packing the molecules form discrete centrosymmetric dimers are through intermolecular N—H···O hydrogen bonds [graph set R₂²(8)] (Bernstein et al., 1995). For further details see Table 1 and Fig. 1.

Related literature top

For the preparation and spectroscopic characterization of a series of related compounds and the crystal structure of 3-[(phenylamino)(p-tolyl)methly]dihydro-2H-thiopyran-4(3H)-one , see: Abaee et al. (2012). For the crystal structures of related compounds, see: Guo et al. (2007); Fun et al. (2009); Harms et al. (2012). For patterns in hydrogen bonding, see: Bernstein et al. (1995). For defining the relative configuration of diastereomers, see: IUPAC (1997).

Experimental top

The title compound was synthesized using an anti-selective three-component Mannich reaction involving the thiopyran-4-one system (Abaee et al., 2012). Colourless crystals suitable for the crystal structure determination were grown from ethyl acetate.

Computing details top

Data collection: EXPOSE (Stoe & Cie, 1994); cell refinement: CELL (Stoe & Cie, 1994); data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: publCIF (Westrip, 2010), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular structure of the title compound with the atom numbering scheme with displacement ellipsoids drawn at 50% probability level. Dashed lines indicate hydrogen bonds to the neighbouring molecule generated by crystallographic inversion symmetry [for symmetry code (i), see Table 1].

rac-3-[(3-Chloroanilino)(4-chlorophenyl)methyl]thian-4-one top

Crystal data top

C₁₈H₁₇Cl₂NOS	F(000) = 760
M_r = 366.29	D_x = 1.428 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8000 reflections
a = 11.2611 (8) Å	θ = 1.9–25°
b = 8.6686 (7) Å	µ = 0.51 mm⁻¹
c = 18.0976 (12) Å	T = 193 K
β = 105.266 (8)°	Plate, colourless
V = 1704.3 (2) Å³	0.29 × 0.24 × 0.05 mm
Z = 4

Data collection top

Stoe IPDS-1 image-plate diffractometer	3134 independent reflections
Radiation source: fine-focus sealed tube	1867 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 6.67 pixels mm^-1	θ_max = 25.4°, θ_min = 1.9°
ω scans	h = −13→13
Absorption correction: integration X-RED32 (Stoe & Cie, 2006)	k = −10→10
T_min = 0.890, T_max = 0.978	l = −21→21
15404 measured reflections

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.048	H atoms treated by a mixture of independent and constrained refinement
S = 0.64	w = 1/[σ²(F_o²) + (0.0127P)²] where P = (F_o² + 2F_c²)/3
3134 reflections	(Δ/σ)_max = 0.001
212 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₈H₁₇Cl₂NOS	V = 1704.3 (2) Å³
M_r = 366.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2611 (8) Å	µ = 0.51 mm⁻¹
b = 8.6686 (7) Å	T = 193 K
c = 18.0976 (12) Å	0.29 × 0.24 × 0.05 mm
β = 105.266 (8)°

Data collection top

Stoe IPDS-1 image-plate diffractometer	3134 independent reflections
Absorption correction: integration X-RED32 (Stoe & Cie, 2006)	1867 reflections with I > 2σ(I)
T_min = 0.890, T_max = 0.978	R_int = 0.042
15404 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.048	H atoms treated by a mixture of independent and constrained refinement
S = 0.64	Δρ_max = 0.17 e Å⁻³
3134 reflections	Δρ_min = −0.15 e Å⁻³
212 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
C2	0.31042 (19)	0.2357 (2)	0.53806 (11)	0.0272 (5)
H2A	0.3860	0.2956	0.5399	0.033*
H2B	0.2797	0.1939	0.4856	0.033*
C3	0.21227 (18)	0.3451 (2)	0.55471 (10)	0.0238 (5)
H3	0.1946	0.4265	0.5141	0.029*
C4	0.09371 (19)	0.2559 (2)	0.54853 (11)	0.0260 (5)
C5	0.10024 (19)	0.1153 (2)	0.59821 (11)	0.0282 (5)
H5A	0.0184	0.0653	0.5864	0.034*
H5B	0.1218	0.1472	0.6527	0.034*
C6	0.19574 (19)	−0.0013 (2)	0.58604 (12)	0.0308 (5)
H6A	0.1703	−0.0387	0.5325	0.037*
H6B	0.1970	−0.0910	0.6201	0.037*
C7	0.25464 (16)	0.4273 (2)	0.63362 (10)	0.0213 (4)
H7	0.2599	0.3478	0.6744	0.026*
C9	0.15786 (17)	0.6196 (2)	0.70276 (11)	0.0221 (4)
C10	0.23976 (18)	0.5889 (2)	0.77388 (11)	0.0251 (4)
H10	0.3020	0.5129	0.7783	0.030*
C11	0.2297 (2)	0.6703 (2)	0.83810 (11)	0.0288 (5)
C12	0.1428 (2)	0.7834 (3)	0.83454 (13)	0.0365 (6)
H12	0.1373	0.8374	0.8792	0.044*
C13	0.06325 (19)	0.8161 (3)	0.76353 (13)	0.0353 (5)
H13	0.0032	0.8948	0.7594	0.042*
C14	0.07008 (18)	0.7357 (2)	0.69860 (12)	0.0277 (5)
H14	0.0145	0.7598	0.6507	0.033*
C15	0.38184 (17)	0.4989 (2)	0.64544 (10)	0.0215 (4)
C16	0.48456 (17)	0.4248 (2)	0.69185 (10)	0.0240 (4)
H16	0.4738	0.3333	0.7182	0.029*
C17	0.60194 (19)	0.4826 (2)	0.70002 (11)	0.0266 (5)
H17	0.6714	0.4305	0.7312	0.032*
C18	0.61680 (18)	0.6159 (2)	0.66259 (10)	0.0242 (4)
C19	0.51657 (18)	0.6941 (2)	0.61697 (11)	0.0278 (5)
H19	0.5278	0.7872	0.5919	0.033*
C20	0.39949 (18)	0.6339 (2)	0.60864 (11)	0.0266 (5)
H20	0.3303	0.6861	0.5772	0.032*
N8	0.15854 (16)	0.5356 (2)	0.63804 (10)	0.0260 (4)
O1	−0.00210 (14)	0.29351 (18)	0.50276 (9)	0.0404 (4)
S1	0.34870 (5)	0.07723 (6)	0.60476 (3)	0.02864 (13)
Cl1	0.33192 (6)	0.62648 (7)	0.92643 (3)	0.04561 (17)
Cl2	0.76515 (5)	0.68900 (7)	0.67408 (3)	0.03580 (14)
H8	0.1180 (19)	0.569 (2)	0.5974 (11)	0.027 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0317 (12)	0.0281 (12)	0.0222 (10)	−0.0019 (10)	0.0076 (9)	−0.0037 (9)
C3	0.0298 (11)	0.0228 (11)	0.0172 (10)	0.0003 (9)	0.0031 (9)	0.0016 (8)
C4	0.0279 (12)	0.0285 (12)	0.0185 (10)	0.0027 (9)	0.0009 (9)	−0.0070 (9)
C5	0.0262 (11)	0.0277 (12)	0.0297 (11)	−0.0043 (10)	0.0058 (9)	0.0001 (10)
C6	0.0331 (12)	0.0244 (11)	0.0335 (12)	−0.0026 (10)	0.0061 (10)	−0.0013 (10)
C7	0.0233 (10)	0.0211 (10)	0.0184 (9)	0.0029 (9)	0.0035 (8)	0.0015 (9)
C9	0.0196 (10)	0.0201 (11)	0.0283 (10)	−0.0057 (9)	0.0095 (9)	−0.0017 (9)
C10	0.0255 (11)	0.0216 (11)	0.0307 (11)	−0.0034 (9)	0.0116 (9)	−0.0013 (9)
C11	0.0309 (12)	0.0298 (13)	0.0284 (11)	−0.0103 (10)	0.0125 (10)	−0.0022 (10)
C12	0.0368 (13)	0.0357 (14)	0.0444 (14)	−0.0102 (11)	0.0239 (11)	−0.0131 (11)
C13	0.0263 (12)	0.0308 (13)	0.0533 (14)	0.0015 (11)	0.0186 (11)	−0.0070 (11)
C14	0.0209 (11)	0.0262 (12)	0.0369 (12)	−0.0015 (9)	0.0095 (9)	0.0000 (10)
C15	0.0255 (11)	0.0220 (10)	0.0166 (10)	0.0021 (9)	0.0045 (8)	−0.0024 (9)
C16	0.0281 (11)	0.0220 (11)	0.0199 (9)	0.0000 (10)	0.0026 (8)	0.0017 (9)
C17	0.0262 (11)	0.0270 (12)	0.0243 (10)	0.0033 (10)	0.0026 (9)	−0.0021 (9)
C18	0.0241 (11)	0.0244 (11)	0.0245 (10)	−0.0013 (9)	0.0072 (8)	−0.0060 (9)
C19	0.0314 (12)	0.0210 (11)	0.0319 (11)	0.0001 (10)	0.0101 (10)	0.0048 (10)
C20	0.0240 (11)	0.0234 (11)	0.0312 (11)	0.0061 (9)	0.0053 (9)	0.0052 (10)
N8	0.0254 (10)	0.0282 (11)	0.0222 (9)	0.0053 (8)	0.0025 (8)	−0.0009 (8)
O1	0.0317 (8)	0.0408 (9)	0.0384 (8)	0.0017 (8)	−0.0090 (7)	0.0025 (8)
S1	0.0268 (3)	0.0258 (3)	0.0316 (3)	0.0030 (3)	0.0046 (2)	0.0003 (2)
Cl1	0.0576 (4)	0.0523 (4)	0.0252 (3)	−0.0036 (3)	0.0077 (3)	−0.0042 (3)
Cl2	0.0269 (3)	0.0373 (3)	0.0424 (3)	−0.0062 (3)	0.0076 (2)	−0.0012 (3)

Geometric parameters (Å, º) top

C2—C3	1.545 (3)	C10—C11	1.389 (3)
C2—S1	1.804 (2)	C10—H10	0.9500
C2—H2A	0.9900	C11—C12	1.375 (3)
C2—H2B	0.9900	C11—Cl1	1.748 (2)
C3—C4	1.521 (3)	C12—C13	1.388 (3)
C3—C7	1.555 (2)	C12—H12	0.9500
C3—H3	1.0000	C13—C14	1.385 (3)
C4—O1	1.219 (2)	C13—H13	0.9500
C4—C5	1.505 (3)	C14—H14	0.9500
C5—C6	1.533 (3)	C15—C20	1.386 (3)
C5—H5A	0.9900	C15—C16	1.395 (3)
C5—H5B	0.9900	C16—C17	1.385 (3)
C6—S1	1.799 (2)	C16—H16	0.9500
C6—H6A	0.9900	C17—C18	1.372 (3)
C6—H6B	0.9900	C17—H17	0.9500
C7—N8	1.451 (2)	C18—C19	1.388 (3)
C7—C15	1.524 (3)	C18—Cl2	1.747 (2)
C7—H7	1.0000	C19—C20	1.389 (3)
C9—N8	1.381 (2)	C19—H19	0.9500
C9—C10	1.397 (3)	C20—H20	0.9500
C9—C14	1.399 (3)	N8—H8	0.81 (2)

C3—C2—S1	113.20 (13)	C11—C10—H10	120.2
C3—C2—H2A	108.9	C9—C10—H10	120.2
S1—C2—H2A	108.9	C12—C11—C10	122.5 (2)
C3—C2—H2B	108.9	C12—C11—Cl1	119.15 (16)
S1—C2—H2B	108.9	C10—C11—Cl1	118.39 (17)
H2A—C2—H2B	107.8	C11—C12—C13	117.82 (19)
C4—C3—C2	109.45 (16)	C11—C12—H12	121.1
C4—C3—C7	110.60 (15)	C13—C12—H12	121.1
C2—C3—C7	113.47 (15)	C14—C13—C12	121.1 (2)
C4—C3—H3	107.7	C14—C13—H13	119.5
C2—C3—H3	107.7	C12—C13—H13	119.5
C7—C3—H3	107.7	C13—C14—C9	120.82 (19)
O1—C4—C5	121.19 (19)	C13—C14—H14	119.6
O1—C4—C3	121.12 (19)	C9—C14—H14	119.6
C5—C4—C3	117.63 (17)	C20—C15—C16	118.50 (18)
C4—C5—C6	111.94 (16)	C20—C15—C7	121.65 (17)
C4—C5—H5A	109.2	C16—C15—C7	119.80 (17)
C6—C5—H5A	109.2	C17—C16—C15	120.98 (19)
C4—C5—H5B	109.2	C17—C16—H16	119.5
C6—C5—H5B	109.2	C15—C16—H16	119.5
H5A—C5—H5B	107.9	C18—C17—C16	119.29 (19)
C5—C6—S1	113.37 (15)	C18—C17—H17	120.4
C5—C6—H6A	108.9	C16—C17—H17	120.4
S1—C6—H6A	108.9	C17—C18—C19	121.32 (19)
C5—C6—H6B	108.9	C17—C18—Cl2	118.95 (16)
S1—C6—H6B	108.9	C19—C18—Cl2	119.73 (16)
H6A—C6—H6B	107.7	C18—C19—C20	118.74 (19)
N8—C7—C15	114.59 (17)	C18—C19—H19	120.6
N8—C7—C3	107.13 (14)	C20—C19—H19	120.6
C15—C7—C3	111.44 (14)	C15—C20—C19	121.15 (19)
N8—C7—H7	107.8	C15—C20—H20	119.4
C15—C7—H7	107.8	C19—C20—H20	119.4
C3—C7—H7	107.8	C9—N8—C7	123.97 (17)
N8—C9—C10	122.09 (18)	C9—N8—H8	116.9 (15)
N8—C9—C14	119.70 (18)	C7—N8—H8	115.6 (14)
C10—C9—C14	118.17 (18)	C6—S1—C2	96.53 (10)
C11—C10—C9	119.63 (19)

S1—C2—C3—C4	−61.14 (18)	C10—C9—C14—C13	−1.2 (3)
S1—C2—C3—C7	62.93 (19)	N8—C7—C15—C20	−46.3 (2)
C2—C3—C4—O1	−120.6 (2)	C3—C7—C15—C20	75.5 (2)
C7—C3—C4—O1	113.7 (2)	N8—C7—C15—C16	136.32 (18)
C2—C3—C4—C5	56.6 (2)	C3—C7—C15—C16	−101.83 (19)
C7—C3—C4—C5	−69.1 (2)	C20—C15—C16—C17	−1.2 (3)
O1—C4—C5—C6	121.5 (2)	C7—C15—C16—C17	176.23 (17)
C3—C4—C5—C6	−55.7 (2)	C15—C16—C17—C18	0.8 (3)
C4—C5—C6—S1	58.2 (2)	C16—C17—C18—C19	0.3 (3)
C4—C3—C7—N8	−61.7 (2)	C16—C17—C18—Cl2	179.32 (15)
C2—C3—C7—N8	174.84 (16)	C17—C18—C19—C20	−0.9 (3)
C4—C3—C7—C15	172.20 (16)	Cl2—C18—C19—C20	180.00 (15)
C2—C3—C7—C15	48.8 (2)	C16—C15—C20—C19	0.5 (3)
N8—C9—C10—C11	−175.75 (18)	C7—C15—C20—C19	−176.88 (18)
C14—C9—C10—C11	1.9 (3)	C18—C19—C20—C15	0.5 (3)
C9—C10—C11—C12	−1.3 (3)	C10—C9—N8—C7	−10.8 (3)
C9—C10—C11—Cl1	178.88 (15)	C14—C9—N8—C7	171.62 (18)
C10—C11—C12—C13	−0.2 (3)	C15—C7—N8—C9	−62.2 (2)
Cl1—C11—C12—C13	179.69 (16)	C3—C7—N8—C9	173.59 (17)
C11—C12—C13—C14	0.9 (3)	C5—C6—S1—C2	−56.47 (16)
C12—C13—C14—C9	−0.3 (3)	C3—C2—S1—C6	58.68 (16)
N8—C9—C14—C13	176.54 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O1ⁱ	0.81 (2)	2.27 (2)	3.070 (2)	168 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇Cl₂NOS
M_r	366.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	11.2611 (8), 8.6686 (7), 18.0976 (12)
β (°)	105.266 (8)
V (Å³)	1704.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.29 × 0.24 × 0.05

Data collection
Diffractometer	Stoe IPDS1 image-plate diffractometer
Absorption correction	Integration X-RED32 (Stoe & Cie, 2006)
T_min, T_max	0.890, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	15404, 3134, 1867
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.048, 0.64
No. of reflections	3134
No. of parameters	212
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.15

Computer programs: EXPOSE (Stoe & Cie, 1994), CELL (Stoe & Cie, 1994), X-RED32 (Stoe & Cie, 2006), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2007), publCIF (Westrip, 2010), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O1ⁱ	0.81 (2)	2.27 (2)	3.070 (2)	168 (2)

Symmetry code: (i) −x, −y+1, −z+1.

References

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Volume 68| Part 3| March 2012| Page o646

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