2-(2H-Benzotriazol-2-yl)-6-[(diethyl-amino)meth-yl]-4-methyl-phenol.

In the title compound, C(18)H(22)N(4)O, the dihedral angle between the planes of the benzotriazol unit and the phenyl ring of the phen-oxy group is 6.4 (2)°. There is an intra-molecular 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 = 310.40

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.123

S = 1.01

3887 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H22N4O	F(000) = 664
Mr = 310.40	Dx = 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

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

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(Fo2) + (0.045P)2 + 0.4268P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3887 reflections	Δρmax = 0.22 e Å−3
209 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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