2-(2H-Benzotriazol-2-yl)-6-[(diethyl­amino)meth­yl]-4-methyl­phenol

Li, J.-Y.; Liu, Y.-C.; Lin, C.-H.; Ko, B.-T.

doi:10.1107/S1600536809036575

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2475

doi:10.1107/S1600536809036575

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2-(2H-Benzotriazol-2-yl)-6-[(diethylamino)methyl]-4-methylphenol

Jia-Ying Li,^a Yi-Chang Liu,^a Chia-Her Lin ^a and Bao-Tsan Ko ^a ^*

^aDepartment of Chemistry, Chung Yuan Christian University, Chung-Li 320, Taiwan
^*Correspondence e-mail: btko@cycu.edu.tw

(Received 8 September 2009; accepted 10 September 2009; online 16 September 2009)

In the title compound, C₁₈H₂₂N₄O, the dihedral angle between the planes of the benzotriazol unit and the phenyl ring of the phenoxy group is 6.4 (2)°. There is an intramolecular O—H⋯N hydrogen bond between the phenol and benzotriazol groups.

Related literature

For background to the applications of aminophenolate zinc compounds in the catalytic ring-opening polymerization of cyclic esters, see: Ejfler et al. (2008 ); Williams et al. (2003 ). For related structures: see: Li et al. (2009 ); Liu et al. (2009 ); Tsai et al. (2009 ).

Experimental

Crystal data

C₁₈H₂₂N₄O
M_r = 310.40
Monoclinic, P 2₁ /c
a = 8.3648 (4) Å
b = 20.0061 (8) Å
c = 10.0340 (4) Å
β = 100.200 (2)°
V = 1652.62 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.45 × 0.30 × 0.28 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.972, T_max = 0.978
16312 measured reflections
3887 independent reflections
2643 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.123
S = 1.01
3887 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H0⋯N1	0.82	1.90	2.621 (2)	146

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536809036575/rk2166sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036575/rk2166Isup2.hkl

checkCIF report

Comment top

Recently, amino-phenolate zinc compounds have been attracting considerable attention, mainly due to their applications in the catalytic ring-opening polymerization of cyclic esters (Ejfler et al., 2008; Williams et al., 2003). These amino-phenolate ligands were easily prepared by Mannich condensation from secondary amine, paraformaldehyde, and 2,4-di-substituted-phenol in the refluxing condition. Moreover, in terms of coordination chemistry, the additional amino group can provide the better chelation to stabilize the transition metal or main group metal complexes. Most recently, our group has successfully synthesized and structural characterized the Pd(II) and Al(III) complexes supported from 4-methyl-2-(2H-benzotriazol-2-yl)-phenolate (BTP) ligand (Li et al., 2009; Tsai et al., 2009). Therefore, our group is interested in the synthesis and preparation of amino-phenolate ligand derived from BTP-H. Herein, we report the synthesis and crystal structure of the title compound, (I), a potential ligand for the preparations of aluminium, palladium and zinc complexes (Scheme 1).

The molecular structure of I is composed of the benzotriazol-phenolate moiety and the diethylamino functionalized group (Fig. 1). The dihedral angle between the planes of the benzotriazol unit and the phenyl ring of the phenoxy group is 6.4 (2)°. There is an intramolecular O—H0···N1 hydrogen bond between the phenol and benzotriazol groups (Tab. 1). The distance of N1···H0 is substantially shorter, than the van der Waals distance of 2.75Å for the N and H distance. It is interesting to note that the six-member ring (O/C1/C2/N2/N1/H0) formed from the O—H···N hydrogen-bond is almost coplanar with the mean deviation of 0.016 (2)Å. Beside H-bonded motif, these bond distances of benzotriazol-phenolate group are similar to those found in the crystal structure of 2-(2H-benzotriazol-2-yl)-4-methylphenyl diphenylphosphinate (Liu et al., 2009).

Related literature top

For background to the applications of aminophenolate zinc compounds in the catalytic ring-opening polymerization of cyclic esters, see: Ejfler et al. (2008); Williams et al. (2003). For related structures: see: Li et al. (2009); Liu et al. (2009); Tsai et al. (2009).

Experimental top

The title compound I was synthesized by the following procedures (Fig. 2): to a mixture of formaldehyde (3.60 g, 120.0 mmol) and diethylamine (12.53 ml, 120.0 mmol) was added 4-methyl-2-(2H-benzotriazol-2-yl)phenol (6.75 g, 30.0 mmol). The resulting mixture was heated under reflux for 2 day and then dried under reduced pressure to yield the oil residue. The residue was extracted with ethyl acetate (3 × 150 ml) and the organic layers were dried over MgSO₄. The final solution was removed the solvent under vacuum to give white solids. Yield: 7.12 g (77%). Colourless crystals were obtained from the saturated hexane solution.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top

	Fig. 1. A view of the molecular structure of I with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Dashed line indicates the intramolecular hydrogen bond.
	Fig. 2. The synthesis path of I.

2-(2H-benzotriazol-2-yl)-6-[(diethylamino)methyl]-4-methylphenol top

Crystal data top

C₁₈H₂₂N₄O	F(000) = 664
M_r = 310.40	D_x = 1.247 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5834 reflections
a = 8.3648 (4) Å	θ = 2.5–27.4°
b = 20.0061 (8) Å	µ = 0.08 mm⁻¹
c = 10.0340 (4) Å	T = 295 K
β = 100.200 (2)°	Block, colourless
V = 1652.62 (12) Å³	0.45 × 0.30 × 0.28 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3887 independent reflections
Radiation source: fine–focus sealed tube	2643 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.3°, θ_min = 2.0°
ϕ– and ω–scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −26→26
T_min = 0.972, T_max = 0.978	l = −11→11
16312 measured reflections

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) = 0.123	w = 1/[σ²(F_o²) + (0.045P)² + 0.4268P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3887 reflections	Δρ_max = 0.22 e Å⁻³
209 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0193 (16)

Crystal data top

C₁₈H₂₂N₄O	V = 1652.62 (12) Å³
M_r = 310.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3648 (4) Å	µ = 0.08 mm⁻¹
b = 20.0061 (8) Å	T = 295 K
c = 10.0340 (4) Å	0.45 × 0.30 × 0.28 mm
β = 100.200 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3887 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2643 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.978	R_int = 0.049
16312 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.01	Δρ_max = 0.22 e Å⁻³
3887 reflections	Δρ_min = −0.19 e Å⁻³
209 parameters

Special details top

Experimental. ¹H NMR (CDCl₃, ppm): δ 6.96–7.97 (6H, m, ArH), 3.83 (2H, s, –CH₂NEt₂), 2.64 (4H, q, –CH₂CH₃), 2.31 (3H, s, ArCH₃), 1.08 (6H, t, –CH₂CH₃).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O	0.38174 (14)	0.59067 (5)	0.55612 (11)	0.0515 (3)
H0	0.4272	0.6187	0.6095	0.077*
N1	0.45310 (16)	0.71135 (6)	0.64977 (13)	0.0428 (3)
N2	0.35464 (15)	0.73474 (6)	0.53973 (12)	0.0370 (3)
N3	0.35122 (17)	0.80050 (6)	0.52295 (13)	0.0431 (3)
N4	0.12557 (16)	0.46827 (6)	0.25528 (13)	0.0450 (3)
C1	0.27977 (18)	0.62176 (7)	0.45473 (14)	0.0372 (3)
C2	0.26092 (18)	0.69109 (7)	0.44291 (14)	0.0359 (3)
C3	0.15528 (18)	0.71937 (7)	0.33526 (15)	0.0387 (4)
H3B	0.1442	0.7656	0.3294	0.046*
C4	0.06657 (18)	0.67937 (8)	0.23680 (15)	0.0396 (4)
C5	0.08776 (18)	0.61034 (8)	0.24786 (15)	0.0411 (4)
H5A	0.0296	0.5831	0.1813	0.049*
C6	0.19162 (19)	0.58095 (7)	0.35372 (15)	0.0389 (4)
C7	0.52040 (19)	0.76738 (8)	0.71051 (15)	0.0399 (4)
C8	0.6352 (2)	0.77626 (9)	0.83005 (17)	0.0519 (4)
H8A	0.6783	0.7402	0.8829	0.062*
C9	0.6802 (2)	0.84032 (9)	0.86450 (18)	0.0567 (5)
H9A	0.7565	0.8478	0.9425	0.068*
C10	0.6153 (2)	0.89575 (9)	0.78609 (18)	0.0564 (5)
H10A	0.6494	0.9385	0.8143	0.068*
C11	0.5046 (2)	0.88836 (8)	0.67066 (18)	0.0522 (4)
H11A	0.4621	0.9250	0.6194	0.063*
C12	0.45687 (19)	0.82249 (7)	0.63192 (15)	0.0399 (4)
C13	−0.0484 (2)	0.70946 (9)	0.11941 (17)	0.0516 (4)
H13A	−0.0474	0.7573	0.1280	0.077*
H13B	−0.1563	0.6931	0.1194	0.077*
H13C	−0.0147	0.6972	0.0361	0.077*
C14	0.2234 (2)	0.50642 (7)	0.36353 (17)	0.0478 (4)
H14A	0.3373	0.4984	0.3617	0.057*
H14B	0.2014	0.4905	0.4498	0.057*
C15	0.2099 (2)	0.40745 (8)	0.22420 (18)	0.0501 (4)
H15A	0.1315	0.3767	0.1745	0.060*
H15B	0.2586	0.3859	0.3082	0.060*
C16	0.3396 (3)	0.42154 (9)	0.1423 (2)	0.0644 (5)
H16A	0.3911	0.3804	0.1244	0.097*
H16B	0.4190	0.4511	0.1919	0.097*
H16C	0.2918	0.4421	0.0582	0.097*
C17	−0.0343 (2)	0.45337 (10)	0.2867 (2)	0.0622 (5)
H17A	−0.0713	0.4915	0.3328	0.075*
H17B	−0.0251	0.4156	0.3482	0.075*
C18	−0.1594 (3)	0.43745 (12)	0.1629 (3)	0.0840 (7)
H18D	−0.2619	0.4283	0.1896	0.126*
H18A	−0.1251	0.3990	0.1181	0.126*
H18B	−0.1708	0.4750	0.1023	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.0601 (8)	0.0407 (6)	0.0447 (7)	0.0052 (5)	−0.0154 (5)	−0.0021 (5)
N1	0.0456 (8)	0.0430 (7)	0.0348 (7)	0.0023 (6)	−0.0065 (6)	−0.0028 (5)
N2	0.0374 (7)	0.0373 (6)	0.0339 (7)	0.0030 (5)	0.0000 (5)	−0.0027 (5)
N3	0.0497 (8)	0.0367 (6)	0.0401 (7)	0.0022 (6)	0.0006 (6)	−0.0014 (5)
N4	0.0456 (8)	0.0400 (7)	0.0465 (8)	−0.0009 (6)	0.0003 (6)	−0.0097 (6)
C1	0.0356 (8)	0.0410 (8)	0.0329 (8)	0.0047 (6)	−0.0002 (6)	−0.0020 (6)
C2	0.0343 (8)	0.0407 (7)	0.0310 (8)	0.0017 (6)	0.0015 (6)	−0.0056 (6)
C3	0.0393 (9)	0.0400 (8)	0.0351 (8)	0.0056 (6)	0.0022 (7)	−0.0012 (6)
C4	0.0345 (8)	0.0500 (9)	0.0326 (8)	0.0037 (6)	0.0017 (6)	−0.0009 (6)
C5	0.0389 (9)	0.0467 (8)	0.0351 (8)	−0.0004 (7)	−0.0007 (7)	−0.0076 (6)
C6	0.0378 (8)	0.0396 (8)	0.0378 (8)	0.0023 (6)	0.0030 (7)	−0.0047 (6)
C7	0.0382 (8)	0.0444 (8)	0.0360 (8)	0.0001 (6)	0.0034 (6)	−0.0060 (6)
C8	0.0514 (11)	0.0586 (10)	0.0408 (10)	0.0004 (8)	−0.0052 (8)	−0.0057 (7)
C9	0.0511 (11)	0.0698 (12)	0.0456 (10)	−0.0101 (9)	−0.0012 (8)	−0.0180 (8)
C10	0.0595 (12)	0.0536 (10)	0.0560 (11)	−0.0137 (8)	0.0103 (9)	−0.0167 (8)
C11	0.0610 (11)	0.0429 (8)	0.0518 (10)	−0.0053 (8)	0.0081 (9)	−0.0058 (7)
C12	0.0392 (8)	0.0433 (8)	0.0366 (8)	−0.0012 (6)	0.0053 (7)	−0.0052 (6)
C13	0.0492 (10)	0.0601 (10)	0.0403 (9)	0.0052 (8)	−0.0059 (8)	0.0024 (7)
C14	0.0519 (10)	0.0415 (8)	0.0449 (10)	0.0034 (7)	−0.0056 (8)	−0.0070 (7)
C15	0.0601 (11)	0.0379 (8)	0.0503 (10)	0.0008 (7)	0.0039 (8)	−0.0049 (7)
C16	0.0789 (15)	0.0567 (11)	0.0610 (12)	0.0135 (10)	0.0216 (11)	0.0026 (9)
C17	0.0537 (12)	0.0640 (12)	0.0686 (13)	−0.0041 (9)	0.0098 (10)	−0.0079 (9)
C18	0.0543 (13)	0.0847 (15)	0.1061 (19)	−0.0137 (11)	−0.0048 (12)	−0.0191 (13)

Geometric parameters (Å, º) top

O—C1	1.3572 (17)	C9—C10	1.412 (3)
O—H0	0.8200	C9—H9A	0.9300
N1—N2	1.3395 (16)	C10—C11	1.357 (2)
N1—C7	1.3503 (19)	C10—H10A	0.9300
N2—N3	1.3259 (16)	C11—C12	1.411 (2)
N2—C2	1.4323 (18)	C11—H11A	0.9300
N3—C12	1.3520 (19)	C13—H13A	0.9600
N4—C14	1.4548 (19)	C13—H13B	0.9600
N4—C17	1.458 (2)	C13—H13C	0.9600
N4—C15	1.4675 (19)	C14—H14A	0.9700
C1—C2	1.399 (2)	C14—H14B	0.9700
C1—C6	1.405 (2)	C15—C16	1.499 (3)
C2—C3	1.389 (2)	C15—H15A	0.9700
C3—C4	1.381 (2)	C15—H15B	0.9700
C3—H3B	0.9300	C16—H16A	0.9600
C4—C5	1.394 (2)	C16—H16B	0.9600
C4—C13	1.508 (2)	C16—H16C	0.9600
C5—C6	1.379 (2)	C17—C18	1.510 (3)
C5—H5A	0.9300	C17—H17A	0.9700
C6—C14	1.515 (2)	C17—H17B	0.9700
C7—C12	1.404 (2)	C18—H18D	0.9600
C7—C8	1.409 (2)	C18—H18A	0.9600
C8—C9	1.363 (2)	C18—H18B	0.9600
C8—H8A	0.9300

C1—O—H0	109.5	C12—C11—H11A	121.5
N2—N1—C7	103.20 (12)	N3—C12—C7	109.07 (13)
N3—N2—N1	116.59 (11)	N3—C12—C11	129.73 (15)
N3—N2—C2	121.46 (12)	C7—C12—C11	121.20 (15)
N1—N2—C2	121.93 (12)	C4—C13—H13A	109.5
N2—N3—C12	102.94 (11)	C4—C13—H13B	109.5
C14—N4—C17	111.20 (14)	H13A—C13—H13B	109.5
C14—N4—C15	111.45 (13)	C4—C13—H13C	109.5
C17—N4—C15	111.75 (13)	H13A—C13—H13C	109.5
O—C1—C2	124.37 (13)	H13B—C13—H13C	109.5
O—C1—C6	117.02 (13)	N4—C14—C6	113.51 (13)
C2—C1—C6	118.58 (13)	N4—C14—H14A	108.9
C3—C2—C1	121.10 (13)	C6—C14—H14A	108.9
C3—C2—N2	118.39 (13)	N4—C14—H14B	108.9
C1—C2—N2	120.48 (12)	C6—C14—H14B	108.9
C4—C3—C2	120.50 (14)	H14A—C14—H14B	107.7
C4—C3—H3B	119.8	N4—C15—C16	112.49 (14)
C2—C3—H3B	119.8	N4—C15—H15A	109.1
C3—C4—C5	118.18 (13)	C16—C15—H15A	109.1
C3—C4—C13	121.00 (14)	N4—C15—H15B	109.1
C5—C4—C13	120.81 (14)	C16—C15—H15B	109.1
C6—C5—C4	122.51 (13)	H15A—C15—H15B	107.8
C6—C5—H5A	118.7	C15—C16—H16A	109.5
C4—C5—H5A	118.7	C15—C16—H16B	109.5
C5—C6—C1	119.12 (13)	H16A—C16—H16B	109.5
C5—C6—C14	123.30 (13)	C15—C16—H16C	109.5
C1—C6—C14	117.50 (13)	H16A—C16—H16C	109.5
N1—C7—C12	108.20 (13)	H16B—C16—H16C	109.5
N1—C7—C8	130.99 (15)	N4—C17—C18	113.18 (17)
C12—C7—C8	120.82 (14)	N4—C17—H17A	108.9
C9—C8—C7	116.78 (16)	C18—C17—H17A	108.9
C9—C8—H8A	121.6	N4—C17—H17B	108.9
C7—C8—H8A	121.6	C18—C17—H17B	108.9
C8—C9—C10	122.39 (17)	H17A—C17—H17B	107.8
C8—C9—H9A	118.8	C17—C18—H18D	109.5
C10—C9—H9A	118.8	C17—C18—H18A	109.5
C11—C10—C9	121.82 (16)	H18D—C18—H18A	109.5
C11—C10—H10A	119.1	C17—C18—H18B	109.5
C9—C10—H10A	119.1	H18D—C18—H18B	109.5
C10—C11—C12	116.99 (16)	H18A—C18—H18B	109.5
C10—C11—H11A	121.5

C7—N1—N2—N3	−0.03 (18)	N2—N1—C7—C12	0.14 (17)
C7—N1—N2—C2	178.32 (13)	N2—N1—C7—C8	−179.45 (17)
N1—N2—N3—C12	−0.08 (17)	N1—C7—C8—C9	179.60 (17)
C2—N2—N3—C12	−178.45 (13)	C12—C7—C8—C9	0.1 (2)
O—C1—C2—C3	179.28 (14)	C7—C8—C9—C10	0.5 (3)
C6—C1—C2—C3	1.2 (2)	C8—C9—C10—C11	−0.5 (3)
O—C1—C2—N2	1.3 (2)	C9—C10—C11—C12	−0.1 (3)
C6—C1—C2—N2	−176.75 (13)	N2—N3—C12—C7	0.16 (16)
N3—N2—C2—C3	−5.1 (2)	N2—N3—C12—C11	−179.77 (17)
N1—N2—C2—C3	176.66 (14)	N1—C7—C12—N3	−0.20 (18)
N3—N2—C2—C1	172.94 (14)	C8—C7—C12—N3	179.44 (15)
N1—N2—C2—C1	−5.3 (2)	N1—C7—C12—C11	179.74 (15)
C1—C2—C3—C4	−0.2 (2)	C8—C7—C12—C11	−0.6 (2)
N2—C2—C3—C4	177.75 (14)	C10—C11—C12—N3	−179.46 (17)
C2—C3—C4—C5	−0.8 (2)	C10—C11—C12—C7	0.6 (3)
C2—C3—C4—C13	−179.95 (15)	C17—N4—C14—C6	−84.24 (18)
C3—C4—C5—C6	0.9 (2)	C15—N4—C14—C6	150.36 (14)
C13—C4—C5—C6	−179.94 (15)	C5—C6—C14—N4	−3.9 (2)
C4—C5—C6—C1	0.1 (2)	C1—C6—C14—N4	179.50 (14)
C4—C5—C6—C14	−176.51 (15)	C14—N4—C15—C16	−76.89 (18)
O—C1—C6—C5	−179.32 (14)	C17—N4—C15—C16	158.01 (16)
C2—C1—C6—C5	−1.1 (2)	C14—N4—C17—C18	158.75 (16)
O—C1—C6—C14	−2.6 (2)	C15—N4—C17—C18	−76.0 (2)
C2—C1—C6—C14	175.67 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O—H0···N1	0.82	1.90	2.621 (2)	146

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₄O
M_r	310.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.3648 (4), 20.0061 (8), 10.0340 (4)
β (°)	100.200 (2)
V (Å³)	1652.62 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.30 × 0.28

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.972, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	16312, 3887, 2643
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.123, 1.01
No. of reflections	3887
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O—H0···N1	0.82	1.902	2.621 (2)	145.8

Acknowledgements

We gratefully acknowledge the financial support in part from the National Science Council, Taiwan (NSC97-2113-M-033-005-MY2) and in part from the project of specific research fields in Chung Yuan Christian University, Taiwan (No. CYCU-98-CR-CH).

References

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