1-(2,3,5,6-Tetra­methyl­benz­yloxy)-1H-benzotriazole

Ravindran Durai Nayagam, B.; Jebas, S.R.; Edward Rajkumar, J.P.; Schollmeyer, D.

doi:10.1107/S1600536809010794

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o917

doi:10.1107/S1600536809010794

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1-(2,3,5,6-Tetramethylbenzyloxy)-1H-benzotriazole

B. Ravindran Durai Nayagam,^a ^* Samuel Robinson Jebas,^b J. P Edward Rajkumar ^c and Dieter Schollmeyer ^d

^aDepartment of Chemistry, Popes College, Sawyerpuram 628 251, Tamilnadu, India, ^bDepartment of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India, ^cDepartment of Physics, Popes College, Sawyerpuram 628 251, Tamilnadu, India, and ^dInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: b_ravidurai@yahoo.com

(Received 20 March 2009; accepted 24 March 2009; online 28 March 2009)

In the title compound, C₁₇H₁₉N₃O, the benzotriazole ring is essentially planar, with a maximum deviation of 0.0069 (15) Å. The mean plane of the benzotriazole ring forms a dihedral angle of 13.16 (4)° with the mean plane of the benzene ring. The crystal packing is stabilized by π–π stacking interactions, with a centroid–centroid distance of 3.8077 (12) Å, together with weak C—H⋯π interactions. Molecules are stacked along the a axis.

Related literature

For bond-length data, see: Allen et al. (1987 ). For the biological activity of N-oxide and benzotriazole derivatives, see: Katarzyna et al. (2005 ); Sarala et al. (2007 ). For applications of benzotriazole, see: Kopec et al. (2008 ); Krawczyk & Gdaniec (2005 ); Smith et al. (2001 ); Sha et al. (1996 ). For 1-hydroxybenzotriazole, see: Anderson et al. (1963 ); Bosch et al. (1983 ).

Experimental

Crystal data

C₁₇H₁₉N₃O
M_r = 281.35
Monoclinic, P 2₁ /c
a = 4.9737 (8) Å
b = 26.3838 (18) Å
c = 11.490 (2) Å
β = 105.977 (7)°
V = 1449.5 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.65 mm⁻¹
T = 193 K
0.51 × 0.51 × 0.45 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (CORINC; Draeger & Gattow, 1971 ) T_min = 0.731, T_max = 0.759
2861 measured reflections
2729 independent reflections
2578 reflections with I > 2σ(I)
R_int = 0.050
3 standard reflections frequency: 60 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.135
S = 1.08
2729 reflections
195 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18C⋯Cg3ⁱ	0.98	2.85	3.6701 (18)	141
C20—H20B⋯Cg3ⁱⁱ	0.98	2.80	3.682 (2)	150
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z. Cg3 is the centroid of the C12–C17 ring.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: CORINC (Draeger & Gattow, 1971); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010794/at2749sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010794/at2749Isup2.hkl

checkCIF report

Comment top

Benzotriazole derivatives show biological activities such as anti-inflammatory, diuretic, antiviral and antihypertensive agents (Katarzyna et al., 2005; Sarala et al., 2007). It is used as a corrosion inhibitor, antifreeze agent, ultraviolet light stabilizer for plastics and as an antifoggant in photography (Krawczyk & Gdaniec, 2005; Smith et al., 2001). N-aryloxy derivatives of benzotriazoles have antimycobacterial activity (Kopec et al., 2008). Benzotriazole possessing three vicinal N atoms, is used as an antifouling and antiwear reagent (Sha et al., 1996). 1-Hydroxybenzotriazole is widely being used as a reagent for peptide synthesis (Anderson et al., 1963). The crystal structure of benzotriazole 1-oxide has been reported (Bosch et al., 1983). Due to the above mentioned applications of benzotriazole we have synthesized and report here the crystal structure of the title compound (I).

The asymmetric unit of (I) comprises of one molecule of the title compound (Fig 1). The bond lengths and angles are found to have normal values (Allen et al., 1987). The benzotriazole ring is essentially planar with the maximum deviation from planarity being 0.0069 (15) Å for atom N2. The mean plane of the benzotriazole ring (N1—N3/C4—C9) forms a dihedral angle of 13.16 (4)° with the mean plane of the phenyl ring (C12—C17).

The crystal packing is stabilized by π—π stacking interactions [Cg1—Cg2ⁱ= of 3.8077 (12) Å; Cg1: (N1—N3/C4—C9); Cg2:(C4—C9): symmetry code:(i) -1+x, y, z] together with weak C—H···π interactions. Molecules are stacked along the a axis (Fig.2).

Related literature top

For bond-length data, see: Allen et al.(1987). For the biological activity of N-oxide and benzotriazole derivatives, see: Katarzyna et al. (2005); Sarala et al. (2007). For applications of benzotriazole, see: Kopec et al. (2008); Krawczyk & Gdaniec (2005); Smith et al. (2001); Sha et al. (1996). For 1-hydroxybenzotriazole, see: Anderson et al. (1963); Bosch et al. (1983). Cg3 is the centroid of the C12–C17 ring.

Experimental top

A mixture of 1-(bromomethyl) 2,3,5,6 tetramethyl benzene (0.227 g, 1 mmol) and sSodium salt of 1-hydroxybenzotriazole (0.1571 mmol) in ethanol (10 ml) was heated at 333 K with stirring for 30 min. The compound formed was filtered off, and dried. The compound was dissolved in ethanol and on slow evaporation crystals suitable for x-ray diffraction are formed.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: CORINC (Draeger & Gattow, 1971); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis. Molecules are stacked along the a axis.

1-(2,3,5,6-Tetramethylbenzyloxy)-1H-benzotriazole top

Crystal data top

C₁₇H₁₉N₃O	F(000) = 600
M_r = 281.35	D_x = 1.289 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 4.9737 (8) Å	θ = 65–70°
b = 26.3838 (18) Å	µ = 0.65 mm⁻¹
c = 11.490 (2) Å	T = 193 K
β = 105.977 (7)°	Block, colourless
V = 1449.5 (4) Å³	0.51 × 0.51 × 0.45 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2578 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.050
Graphite monochromator	θ_max = 69.9°, θ_min = 3.4°
ω/2θ scans	h = −5→6
Absorption correction: ψ scan (CORINC; Draeger & Gattow, 1971)	k = 0→32
T_min = 0.731, T_max = 0.759	l = −13→0
2861 measured reflections	3 standard reflections every 60 min
2729 independent reflections	intensity decay: 1%

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0664P)² + 0.687P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.002
2729 reflections	Δρ_max = 0.27 e Å⁻³
195 parameters	Δρ_min = −0.23 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: 0.0042 (6)

Crystal data top

C₁₇H₁₉N₃O	V = 1449.5 (4) Å³
M_r = 281.35	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 4.9737 (8) Å	µ = 0.65 mm⁻¹
b = 26.3838 (18) Å	T = 193 K
c = 11.490 (2) Å	0.51 × 0.51 × 0.45 mm
β = 105.977 (7)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2578 reflections with I > 2σ(I)
Absorption correction: ψ scan (CORINC; Draeger & Gattow, 1971)	R_int = 0.050
T_min = 0.731, T_max = 0.759	3 standard reflections every 60 min
2861 measured reflections	intensity decay: 1%
2729 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.08	Δρ_max = 0.27 e Å⁻³
2729 reflections	Δρ_min = −0.23 e Å⁻³
195 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
N1	0.4809 (3)	0.32620 (5)	0.62810 (11)	0.0311 (3)
N2	0.3357 (3)	0.28455 (5)	0.63903 (13)	0.0379 (4)
N3	0.4680 (3)	0.26168 (5)	0.73894 (13)	0.0395 (4)
C4	0.7028 (3)	0.28997 (6)	0.79380 (14)	0.0321 (4)
C5	0.9114 (4)	0.28229 (6)	0.90326 (15)	0.0374 (4)
H5	0.9065	0.2539	0.9536	0.045*
C6	1.1208 (4)	0.31732 (7)	0.93407 (15)	0.0411 (4)
H6	1.2652	0.3131	1.0072	0.049*
C7	1.1281 (4)	0.35962 (7)	0.86002 (16)	0.0412 (4)
H7	1.2779	0.3831	0.8849	0.049*
C8	0.9264 (3)	0.36815 (6)	0.75324 (15)	0.0348 (4)
H8	0.9317	0.3967	0.7036	0.042*
C9	0.7132 (3)	0.33208 (6)	0.72239 (13)	0.0292 (4)
O10	0.3754 (2)	0.35998 (4)	0.53578 (9)	0.0327 (3)
C11	0.4691 (4)	0.34745 (6)	0.42841 (14)	0.0328 (4)
H11A	0.3904	0.3145	0.3939	0.039*
H11B	0.6757	0.3455	0.4497	0.039*
C12	0.3636 (3)	0.38958 (6)	0.33973 (13)	0.0286 (4)
C13	0.5113 (3)	0.43544 (6)	0.35296 (13)	0.0296 (4)
C14	0.4080 (3)	0.47548 (6)	0.27302 (14)	0.0316 (4)
C15	0.1584 (3)	0.46843 (6)	0.18303 (14)	0.0335 (4)
H15	0.0869	0.4957	0.1294	0.040*
C16	0.0095 (3)	0.42330 (7)	0.16838 (13)	0.0318 (4)
C17	0.1116 (3)	0.38296 (6)	0.24756 (13)	0.0299 (4)
C18	0.7813 (3)	0.44365 (7)	0.45103 (15)	0.0389 (4)
H18A	0.8466	0.4113	0.4906	0.058*
H18B	0.7492	0.4676	0.5110	0.058*
H18C	0.9231	0.4574	0.4151	0.058*
C19	0.5633 (4)	0.52490 (7)	0.28165 (18)	0.0424 (4)
H19A	0.7451	0.5190	0.2664	0.064*
H19B	0.5917	0.5392	0.3628	0.064*
H19C	0.4541	0.5487	0.2214	0.064*
C20	−0.2599 (4)	0.41887 (8)	0.06843 (15)	0.0416 (4)
H20A	−0.3033	0.4515	0.0268	0.062*
H20B	−0.4120	0.4093	0.1031	0.062*
H20C	−0.2393	0.3929	0.0106	0.062*
C21	−0.0499 (4)	0.33394 (7)	0.23361 (17)	0.0399 (4)
H21A	−0.0717	0.3235	0.3124	0.060*
H21B	0.0518	0.3076	0.2029	0.060*
H21C	−0.2348	0.3388	0.1765	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0347 (7)	0.0312 (7)	0.0230 (6)	−0.0011 (5)	0.0005 (5)	0.0022 (5)
N2	0.0426 (8)	0.0353 (8)	0.0313 (7)	−0.0056 (6)	0.0026 (6)	−0.0011 (6)
N3	0.0478 (9)	0.0343 (8)	0.0321 (7)	−0.0046 (6)	0.0038 (6)	0.0008 (6)
C4	0.0364 (8)	0.0301 (8)	0.0273 (8)	0.0026 (6)	0.0048 (6)	−0.0007 (6)
C5	0.0464 (10)	0.0351 (9)	0.0268 (8)	0.0078 (7)	0.0035 (7)	0.0042 (6)
C6	0.0385 (9)	0.0508 (10)	0.0275 (8)	0.0071 (8)	−0.0018 (7)	−0.0006 (7)
C7	0.0345 (9)	0.0477 (10)	0.0355 (9)	−0.0059 (7)	−0.0002 (7)	−0.0041 (7)
C8	0.0370 (9)	0.0347 (8)	0.0298 (8)	−0.0028 (7)	0.0044 (7)	0.0011 (6)
C9	0.0301 (8)	0.0318 (8)	0.0233 (7)	0.0041 (6)	0.0033 (6)	−0.0019 (6)
O10	0.0379 (6)	0.0353 (6)	0.0213 (5)	0.0086 (5)	0.0021 (4)	0.0026 (4)
C11	0.0380 (9)	0.0338 (8)	0.0248 (8)	0.0063 (7)	0.0055 (6)	−0.0015 (6)
C12	0.0305 (8)	0.0325 (8)	0.0222 (7)	0.0049 (6)	0.0062 (6)	−0.0013 (6)
C13	0.0281 (8)	0.0357 (8)	0.0240 (7)	0.0018 (6)	0.0057 (6)	−0.0040 (6)
C14	0.0339 (8)	0.0331 (8)	0.0295 (8)	0.0019 (6)	0.0114 (6)	−0.0019 (6)
C15	0.0349 (8)	0.0374 (9)	0.0275 (8)	0.0089 (7)	0.0077 (6)	0.0051 (6)
C16	0.0293 (8)	0.0428 (9)	0.0219 (7)	0.0046 (7)	0.0048 (6)	−0.0019 (6)
C17	0.0305 (8)	0.0351 (8)	0.0237 (7)	0.0011 (6)	0.0070 (6)	−0.0040 (6)
C18	0.0338 (9)	0.0460 (10)	0.0320 (9)	−0.0027 (7)	0.0009 (7)	−0.0053 (7)
C19	0.0456 (10)	0.0354 (9)	0.0483 (10)	−0.0028 (8)	0.0163 (8)	−0.0016 (8)
C20	0.0344 (9)	0.0580 (11)	0.0266 (8)	0.0056 (8)	−0.0012 (7)	−0.0019 (7)
C21	0.0380 (9)	0.0401 (9)	0.0403 (9)	−0.0046 (7)	0.0086 (7)	−0.0045 (7)

Geometric parameters (Å, º) top

N1—N2	1.3398 (19)	C13—C14	1.401 (2)
N1—C9	1.358 (2)	C13—C18	1.512 (2)
N1—O10	1.3741 (16)	C14—C15	1.392 (2)
N2—N3	1.304 (2)	C14—C19	1.505 (2)
N3—C4	1.383 (2)	C15—C16	1.388 (2)
C4—C9	1.390 (2)	C15—H15	0.9500
C4—C5	1.407 (2)	C16—C17	1.401 (2)
C5—C6	1.364 (3)	C16—C20	1.510 (2)
C5—H5	0.9500	C17—C21	1.508 (2)
C6—C7	1.410 (3)	C18—H18A	0.9800
C6—H6	0.9500	C18—H18B	0.9800
C7—C8	1.373 (2)	C18—H18C	0.9800
C7—H7	0.9500	C19—H19A	0.9800
C8—C9	1.396 (2)	C19—H19B	0.9800
C8—H8	0.9500	C19—H19C	0.9800
O10—C11	1.4714 (19)	C20—H20A	0.9800
C11—C12	1.501 (2)	C20—H20B	0.9800
C11—H11A	0.9900	C20—H20C	0.9800
C11—H11B	0.9900	C21—H21A	0.9800
C12—C13	1.402 (2)	C21—H21B	0.9800
C12—C17	1.412 (2)	C21—H21C	0.9800

N2—N1—C9	112.41 (13)	C15—C14—C13	118.49 (15)
N2—N1—O10	120.21 (12)	C15—C14—C19	120.09 (15)
C9—N1—O10	127.02 (13)	C13—C14—C19	121.41 (15)
N3—N2—N1	107.93 (13)	C16—C15—C14	122.80 (15)
N2—N3—C4	108.04 (14)	C16—C15—H15	118.6
N3—C4—C9	109.04 (14)	C14—C15—H15	118.6
N3—C4—C5	130.67 (16)	C15—C16—C17	119.15 (14)
C9—C4—C5	120.29 (15)	C15—C16—C20	119.39 (15)
C6—C5—C4	117.17 (16)	C17—C16—C20	121.45 (16)
C6—C5—H5	121.4	C16—C17—C12	118.77 (15)
C4—C5—H5	121.4	C16—C17—C21	119.69 (14)
C5—C6—C7	121.62 (16)	C12—C17—C21	121.53 (14)
C5—C6—H6	119.2	C13—C18—H18A	109.5
C7—C6—H6	119.2	C13—C18—H18B	109.5
C8—C7—C6	122.35 (16)	H18A—C18—H18B	109.5
C8—C7—H7	118.8	C13—C18—H18C	109.5
C6—C7—H7	118.8	H18A—C18—H18C	109.5
C7—C8—C9	115.62 (15)	H18B—C18—H18C	109.5
C7—C8—H8	122.2	C14—C19—H19A	109.5
C9—C8—H8	122.2	C14—C19—H19B	109.5
N1—C9—C4	102.58 (14)	H19A—C19—H19B	109.5
N1—C9—C8	134.47 (15)	C14—C19—H19C	109.5
C4—C9—C8	122.95 (15)	H19A—C19—H19C	109.5
N1—O10—C11	111.09 (11)	H19B—C19—H19C	109.5
O10—C11—C12	105.69 (12)	C16—C20—H20A	109.5
O10—C11—H11A	110.6	C16—C20—H20B	109.5
C12—C11—H11A	110.6	H20A—C20—H20B	109.5
O10—C11—H11B	110.6	C16—C20—H20C	109.5
C12—C11—H11B	110.6	H20A—C20—H20C	109.5
H11A—C11—H11B	108.7	H20B—C20—H20C	109.5
C13—C12—C17	121.24 (14)	C17—C21—H21A	109.5
C13—C12—C11	119.37 (14)	C17—C21—H21B	109.5
C17—C12—C11	119.33 (14)	H21A—C21—H21B	109.5
C14—C13—C12	119.53 (14)	C17—C21—H21C	109.5
C14—C13—C18	118.07 (15)	H21A—C21—H21C	109.5
C12—C13—C18	122.39 (14)	H21B—C21—H21C	109.5

C9—N1—N2—N3	−0.72 (19)	O10—C11—C12—C13	80.40 (17)
O10—N1—N2—N3	−174.26 (13)	O10—C11—C12—C17	−97.09 (16)
N1—N2—N3—C4	0.67 (18)	C17—C12—C13—C14	−0.3 (2)
N2—N3—C4—C9	−0.41 (19)	C11—C12—C13—C14	−177.69 (14)
N2—N3—C4—C5	179.01 (17)	C17—C12—C13—C18	179.83 (14)
N3—C4—C5—C6	179.99 (17)	C11—C12—C13—C18	2.4 (2)
C9—C4—C5—C6	−0.6 (2)	C12—C13—C14—C15	0.6 (2)
C4—C5—C6—C7	0.3 (3)	C18—C13—C14—C15	−179.49 (14)
C5—C6—C7—C8	0.1 (3)	C12—C13—C14—C19	−178.35 (14)
C6—C7—C8—C9	−0.1 (3)	C18—C13—C14—C19	1.6 (2)
N2—N1—C9—C4	0.44 (17)	C13—C14—C15—C16	−0.7 (2)
O10—N1—C9—C4	173.45 (14)	C19—C14—C15—C16	178.23 (15)
N2—N1—C9—C8	−179.69 (17)	C14—C15—C16—C17	0.5 (2)
O10—N1—C9—C8	−6.7 (3)	C14—C15—C16—C20	179.92 (15)
N3—C4—C9—N1	−0.01 (17)	C15—C16—C17—C12	−0.1 (2)
C5—C4—C9—N1	−179.51 (15)	C20—C16—C17—C12	−179.53 (14)
N3—C4—C9—C8	−179.90 (15)	C15—C16—C17—C21	179.26 (14)
C5—C4—C9—C8	0.6 (2)	C20—C16—C17—C21	−0.2 (2)
C7—C8—C9—N1	179.94 (17)	C13—C12—C17—C16	0.0 (2)
C7—C8—C9—C4	−0.2 (2)	C11—C12—C17—C16	177.45 (13)
N2—N1—O10—C11	−91.18 (17)	C13—C12—C17—C21	−179.36 (14)
C9—N1—O10—C11	96.30 (17)	C11—C12—C17—C21	−1.9 (2)
N1—O10—C11—C12	−174.71 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18C···Cg3ⁱ	0.98	2.85	3.6701 (18)	141
C20—H20B···Cg3ⁱⁱ	0.98	2.80	3.682 (2)	150

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉N₃O
M_r	281.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	4.9737 (8), 26.3838 (18), 11.490 (2)
β (°)	105.977 (7)
V (Å³)	1449.5 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.51 × 0.51 × 0.45

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (CORINC; Draeger & Gattow, 1971)
T_min, T_max	0.731, 0.759
No. of measured, independent and observed [I > 2σ(I)] reflections	2861, 2729, 2578
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.135, 1.08
No. of reflections	2729
No. of parameters	195
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.23

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CORINC (Draeger & Gattow, 1971), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18C···Cg3ⁱ	0.98	2.85	3.6701 (18)	141
C20—H20B···Cg3ⁱⁱ	0.98	2.80	3.682 (2)	150

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

References

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Volume 65| Part 4| April 2009| Page o917

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