Ethyl 4-[(3,5-di-tert-butyl-2-hy-droxy-benzyl-idene)-amino]-benzoate.

The title compound, a Schiff base, C(24)H(31)NO(3), has a substituted aromatic ring at both ends of the azomethine linkage and these make a dihedral angle of 24.9 (1)°. There is an intra-molecular hydrogen bond between the hy-droxy group (donor) and the N atom of themazomethine linkage.

Related literature

For the use of the methyl ester analog of the title compound as a second-harmonic generation material, see: Sliwa et al. (2008 ▶).

Experimental

Crystal data

C24H31NO3

M = 381.50

Monoclinic,

a = 18.4789 (18) Å

b = 10.7194 (11) Å

c = 10.7768 (10) Å

β = 97.437 (2)°

V = 2116.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.30 × 0.05 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

19941 measured reflections

4855 independent reflections

3123 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.142

S = 1.01

4855 reflections

257 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.64 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041383/fl2320sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041383/fl2320Isup2.hkl

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

C24H31NO3	F(000) = 824
Mr = 381.50	Dx = 1.197 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.4789 (18) Å	Cell parameters from 2280 reflections
b = 10.7194 (11) Å	θ = 2.2–23.8°
c = 10.7768 (10) Å	µ = 0.08 mm−1
β = 97.437 (2)°	T = 100 K
V = 2116.7 (4) Å3	Prism, orange
Z = 4	0.30 × 0.05 × 0.05 mm

Bruker SMART APEX diffractometer	3123 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.065
graphite	θmax = 27.5°, θmin = 2.2°
ω scans	h = −24→23
19941 measured reflections	k = −13→13
4855 independent reflections	l = −13→14

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0558P)2 + 1.1473P] where P = (Fo2 + 2Fc2)/3
4855 reflections	(Δ/σ)max = 0.001
257 parameters	Δρmax = 0.64 e Å−3
1 restraint	Δρmin = −0.25 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.78175 (8)	0.89233 (13)	0.62825 (14)	0.0252 (3)
H1	0.7466 (13)	0.885 (3)	0.567 (2)	0.086 (12)*
O2	0.42198 (8)	0.93692 (14)	0.03223 (14)	0.0291 (4)
O3	0.43875 (7)	0.73467 (13)	−0.01081 (13)	0.0237 (3)
N1	0.67954 (9)	0.79668 (16)	0.46645 (16)	0.0222 (4)
C1	0.78970 (11)	0.77878 (18)	0.68363 (19)	0.0203 (4)
C2	0.84179 (10)	0.76051 (18)	0.78972 (18)	0.0186 (4)
C3	0.85050 (10)	0.63866 (18)	0.83515 (18)	0.0180 (4)
H3	0.8862	0.6243	0.9054	0.022*
C4	0.80999 (10)	0.53616 (18)	0.78384 (18)	0.0183 (4)
C5	0.75592 (10)	0.56031 (19)	0.68469 (18)	0.0199 (4)
H5	0.7253	0.4941	0.6509	0.024*
C6	0.74560 (10)	0.67938 (19)	0.63368 (18)	0.0201 (4)
C7	0.94204 (12)	0.9088 (2)	0.7566 (2)	0.0290 (5)
H7A	0.9137	0.9359	0.6780	0.044*
H7B	0.9735	0.8388	0.7402	0.044*
H7C	0.9722	0.9782	0.7930	0.044*
C8	0.88965 (11)	0.86740 (19)	0.84883 (19)	0.0219 (4)
C9	0.84263 (13)	0.9784 (2)	0.8811 (2)	0.0295 (5)
H9A	0.8124	1.0072	0.8051	0.044*
H9B	0.8744	1.0464	0.9158	0.044*
H9C	0.8112	0.9521	0.9428	0.044*
C10	0.93590 (13)	0.8274 (2)	0.9709 (2)	0.0304 (5)
H10A	0.9670	0.7569	0.9542	0.046*
H10B	0.9037	0.8024	1.0320	0.046*
H10C	0.9665	0.8974	1.0044	0.046*
C11	0.82432 (11)	0.40232 (18)	0.82969 (18)	0.0197 (4)
C12	0.75683 (11)	0.3511 (2)	0.8825 (2)	0.0254 (5)
H12A	0.7465	0.4030	0.9529	0.038*
H12B	0.7662	0.2652	0.9111	0.038*
H12C	0.7148	0.3526	0.8169	0.038*
C13	0.84080 (12)	0.3212 (2)	0.7192 (2)	0.0259 (5)
H13A	0.8838	0.3540	0.6858	0.039*
H13B	0.7988	0.3225	0.6535	0.039*
H13C	0.8502	0.2352	0.7479	0.039*
C14	0.88904 (11)	0.3930 (2)	0.9334 (2)	0.0247 (5)
H14A	0.9330	0.4251	0.9025	0.037*
H14B	0.8966	0.3056	0.9583	0.037*
H14C	0.8789	0.4423	1.0057	0.037*
C15	0.68922 (11)	0.69415 (19)	0.52586 (19)	0.0219 (4)
H15	0.6589	0.6250	0.4995	0.026*
C16	0.62487 (10)	0.8028 (2)	0.36008 (19)	0.0213 (4)
C17	0.59190 (11)	0.9167 (2)	0.3314 (2)	0.0235 (5)
H17	0.6062	0.9876	0.3815	0.028*
C18	0.53831 (11)	0.9279 (2)	0.23032 (19)	0.0228 (5)
H18	0.5157	1.0064	0.2116	0.027*
C19	0.51707 (10)	0.82475 (19)	0.15535 (19)	0.0202 (4)
C20	0.55214 (11)	0.7112 (2)	0.18075 (19)	0.0214 (4)
H20	0.5391	0.6411	0.1286	0.026*
C21	0.60615 (11)	0.7002 (2)	0.28224 (19)	0.0234 (5)
H21	0.6305	0.6228	0.2990	0.028*
C22	0.45526 (11)	0.84073 (19)	0.05346 (19)	0.0209 (4)
C23	0.37799 (11)	0.7442 (2)	−0.1100 (2)	0.0265 (5)
H23A	0.3908	0.8002	−0.1768	0.032*
H23B	0.3347	0.7788	−0.0767	0.032*
C24	0.36159 (12)	0.6163 (2)	−0.1613 (2)	0.0281 (5)
H24A	0.3206	0.6204	−0.2286	0.042*
H24B	0.3488	0.5616	−0.0945	0.042*
H24C	0.4046	0.5830	−0.1944	0.042*

	U11	U22	U33	U12	U13	U23
O1	0.0265 (8)	0.0202 (8)	0.0271 (8)	−0.0029 (6)	−0.0030 (7)	0.0048 (6)
O2	0.0308 (8)	0.0244 (8)	0.0291 (8)	0.0063 (7)	−0.0075 (7)	0.0009 (7)
O3	0.0216 (7)	0.0233 (8)	0.0235 (8)	0.0036 (6)	−0.0069 (6)	−0.0009 (6)
N1	0.0198 (8)	0.0244 (9)	0.0225 (9)	0.0007 (7)	0.0031 (7)	0.0006 (8)
C1	0.0218 (10)	0.0195 (10)	0.0202 (10)	0.0052 (8)	0.0057 (8)	0.0059 (8)
C2	0.0173 (9)	0.0200 (10)	0.0187 (10)	0.0001 (8)	0.0031 (8)	0.0001 (8)
C3	0.0162 (9)	0.0229 (10)	0.0143 (9)	0.0016 (8)	−0.0008 (8)	0.0021 (8)
C4	0.0165 (9)	0.0206 (10)	0.0178 (10)	0.0008 (8)	0.0023 (8)	0.0009 (8)
C5	0.0173 (9)	0.0229 (11)	0.0191 (10)	−0.0008 (8)	0.0011 (8)	−0.0032 (8)
C6	0.0154 (9)	0.0273 (11)	0.0173 (10)	0.0025 (8)	0.0004 (8)	0.0000 (9)
C7	0.0294 (12)	0.0291 (12)	0.0286 (12)	−0.0085 (9)	0.0037 (10)	0.0017 (10)
C8	0.0252 (10)	0.0193 (10)	0.0204 (10)	−0.0026 (8)	0.0000 (8)	0.0017 (8)
C9	0.0393 (13)	0.0220 (11)	0.0273 (12)	−0.0012 (10)	0.0047 (10)	−0.0015 (9)
C10	0.0351 (12)	0.0253 (12)	0.0275 (12)	−0.0087 (10)	−0.0080 (10)	0.0024 (10)
C11	0.0201 (10)	0.0191 (10)	0.0192 (10)	0.0004 (8)	0.0002 (8)	−0.0015 (8)
C12	0.0262 (11)	0.0220 (11)	0.0280 (12)	−0.0025 (9)	0.0031 (9)	0.0009 (9)
C13	0.0309 (11)	0.0232 (11)	0.0232 (11)	0.0051 (9)	0.0023 (9)	−0.0025 (9)
C14	0.0269 (11)	0.0202 (11)	0.0254 (11)	0.0022 (9)	−0.0024 (9)	0.0009 (9)
C15	0.0212 (10)	0.0212 (11)	0.0235 (11)	−0.0011 (8)	0.0039 (8)	−0.0020 (9)
C16	0.0170 (9)	0.0283 (12)	0.0184 (10)	0.0001 (8)	0.0014 (8)	0.0009 (9)
C17	0.0216 (10)	0.0247 (11)	0.0238 (11)	−0.0014 (9)	0.0013 (9)	−0.0008 (9)
C18	0.0226 (10)	0.0227 (11)	0.0227 (11)	0.0021 (8)	0.0012 (9)	0.0015 (9)
C19	0.0187 (10)	0.0239 (11)	0.0174 (10)	0.0028 (8)	0.0004 (8)	0.0021 (8)
C20	0.0205 (10)	0.0228 (11)	0.0204 (10)	−0.0005 (8)	0.0016 (8)	0.0003 (9)
C21	0.0216 (10)	0.0241 (11)	0.0238 (11)	0.0060 (9)	0.0004 (8)	0.0039 (9)
C22	0.0194 (10)	0.0232 (11)	0.0198 (10)	0.0001 (8)	0.0012 (8)	0.0020 (9)
C23	0.0240 (11)	0.0295 (12)	0.0231 (11)	0.0018 (9)	−0.0082 (9)	0.0016 (9)
C24	0.0261 (11)	0.0306 (12)	0.0271 (12)	−0.0001 (10)	0.0012 (9)	−0.0006 (10)

O1—C1	1.355 (2)	C11—C14	1.531 (3)
O1—H1	0.866 (10)	C11—C13	1.537 (3)
O2—C22	1.207 (2)	C11—C12	1.537 (3)
O3—C22	1.346 (2)	C12—H12A	0.9800
O3—C23	1.450 (2)	C12—H12B	0.9800
N1—C15	1.273 (3)	C12—H12C	0.9800
N1—C16	1.428 (3)	C13—H13A	0.9800
C1—C6	1.406 (3)	C13—H13B	0.9800
C1—C2	1.410 (3)	C13—H13C	0.9800
C2—C3	1.397 (3)	C14—H14A	0.9800
C2—C8	1.535 (3)	C14—H14B	0.9800
C3—C4	1.402 (3)	C14—H14C	0.9800
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.389 (3)	C16—C17	1.381 (3)
C4—C11	1.529 (3)	C16—C21	1.399 (3)
C5—C6	1.393 (3)	C17—C18	1.379 (3)
C5—H5	0.9500	C17—H17	0.9500
C6—C15	1.465 (3)	C18—C19	1.395 (3)
C7—C8	1.540 (3)	C18—H18	0.9500
C7—H7A	0.9800	C19—C20	1.389 (3)
C7—H7B	0.9800	C19—C22	1.488 (3)
C7—H7C	0.9800	C20—C21	1.387 (3)
C8—C10	1.534 (3)	C20—H20	0.9500
C8—C9	1.539 (3)	C21—H21	0.9500
C9—H9A	0.9800	C23—C24	1.494 (3)
C9—H9B	0.9800	C23—H23A	0.9900
C9—H9C	0.9800	C23—H23B	0.9900
C10—H10A	0.9800	C24—H24A	0.9800
C10—H10B	0.9800	C24—H24B	0.9800
C10—H10C	0.9800	C24—H24C	0.9800
C1—O1—H1	106 (2)	H12A—C12—H12B	109.5
C22—O3—C23	114.99 (16)	C11—C12—H12C	109.5
C15—N1—C16	118.83 (18)	H12A—C12—H12C	109.5
O1—C1—C6	119.20 (18)	H12B—C12—H12C	109.5
O1—C1—C2	120.37 (18)	C11—C13—H13A	109.5
C6—C1—C2	120.43 (18)	C11—C13—H13B	109.5
C3—C2—C1	116.73 (18)	H13A—C13—H13B	109.5
C3—C2—C8	121.24 (17)	C11—C13—H13C	109.5
C1—C2—C8	121.96 (18)	H13A—C13—H13C	109.5
C2—C3—C4	124.26 (18)	H13B—C13—H13C	109.5
C2—C3—H3	117.9	C11—C14—H14A	109.5
C4—C3—H3	117.9	C11—C14—H14B	109.5
C5—C4—C3	116.83 (18)	H14A—C14—H14B	109.5
C5—C4—C11	120.03 (17)	C11—C14—H14C	109.5
C3—C4—C11	123.12 (17)	H14A—C14—H14C	109.5
C4—C5—C6	121.49 (19)	H14B—C14—H14C	109.5
C4—C5—H5	119.3	N1—C15—C6	122.09 (19)
C6—C5—H5	119.3	N1—C15—H15	119.0
C5—C6—C1	120.03 (18)	C6—C15—H15	119.0
C5—C6—C15	117.32 (18)	C17—C16—C21	119.51 (19)
C1—C6—C15	122.63 (19)	C17—C16—N1	117.79 (19)
C8—C7—H7A	109.5	C21—C16—N1	122.64 (19)
C8—C7—H7B	109.5	C18—C17—C16	120.3 (2)
H7A—C7—H7B	109.5	C18—C17—H17	119.8
C8—C7—H7C	109.5	C16—C17—H17	119.8
H7A—C7—H7C	109.5	C17—C18—C19	120.5 (2)
H7B—C7—H7C	109.5	C17—C18—H18	119.7
C10—C8—C2	112.00 (17)	C19—C18—H18	119.7
C10—C8—C7	107.87 (18)	C20—C19—C18	119.40 (18)
C2—C8—C7	108.92 (17)	C20—C19—C22	122.69 (19)
C10—C8—C9	106.89 (17)	C18—C19—C22	117.87 (18)
C2—C8—C9	111.03 (17)	C21—C20—C19	120.0 (2)
C7—C8—C9	110.07 (18)	C21—C20—H20	120.0
C8—C9—H9A	109.5	C19—C20—H20	120.0
C8—C9—H9B	109.5	C20—C21—C16	120.18 (19)
H9A—C9—H9B	109.5	C20—C21—H21	119.9
C8—C9—H9C	109.5	C16—C21—H21	119.9
H9A—C9—H9C	109.5	O2—C22—O3	123.23 (18)
H9B—C9—H9C	109.5	O2—C22—C19	124.17 (19)
C8—C10—H10A	109.5	O3—C22—C19	112.57 (17)
C8—C10—H10B	109.5	O3—C23—C24	107.99 (17)
H10A—C10—H10B	109.5	O3—C23—H23A	110.1
C8—C10—H10C	109.5	C24—C23—H23A	110.1
H10A—C10—H10C	109.5	O3—C23—H23B	110.1
H10B—C10—H10C	109.5	C24—C23—H23B	110.1
C4—C11—C14	112.55 (16)	H23A—C23—H23B	108.4
C4—C11—C13	108.92 (16)	C23—C24—H24A	109.5
C14—C11—C13	108.30 (16)	C23—C24—H24B	109.5
C4—C11—C12	109.85 (16)	H24A—C24—H24B	109.5
C14—C11—C12	107.53 (17)	C23—C24—H24C	109.5
C13—C11—C12	109.64 (17)	H24A—C24—H24C	109.5
C11—C12—H12A	109.5	H24B—C24—H24C	109.5
C11—C12—H12B	109.5
O1—C1—C2—C3	−175.11 (17)	C3—C4—C11—C13	−122.2 (2)
C6—C1—C2—C3	4.6 (3)	C5—C4—C11—C12	−64.1 (2)
O1—C1—C2—C8	1.8 (3)	C3—C4—C11—C12	117.6 (2)
C6—C1—C2—C8	−178.52 (18)	C16—N1—C15—C6	178.21 (17)
C1—C2—C3—C4	−1.5 (3)	C5—C6—C15—N1	−174.29 (19)
C8—C2—C3—C4	−178.36 (18)	C1—C6—C15—N1	4.0 (3)
C2—C3—C4—C5	−2.7 (3)	C15—N1—C16—C17	151.3 (2)
C2—C3—C4—C11	175.58 (19)	C15—N1—C16—C21	−31.4 (3)
C3—C4—C5—C6	3.9 (3)	C21—C16—C17—C18	3.2 (3)
C11—C4—C5—C6	−174.44 (18)	N1—C16—C17—C18	−179.46 (18)
C4—C5—C6—C1	−0.9 (3)	C16—C17—C18—C19	−0.4 (3)
C4—C5—C6—C15	177.43 (18)	C17—C18—C19—C20	−2.2 (3)
O1—C1—C6—C5	176.18 (18)	C17—C18—C19—C22	175.61 (19)
C2—C1—C6—C5	−3.5 (3)	C18—C19—C20—C21	2.0 (3)
O1—C1—C6—C15	−2.1 (3)	C22—C19—C20—C21	−175.68 (18)
C2—C1—C6—C15	178.18 (18)	C19—C20—C21—C16	0.8 (3)
C3—C2—C8—C10	−9.4 (3)	C17—C16—C21—C20	−3.4 (3)
C1—C2—C8—C10	173.86 (19)	N1—C16—C21—C20	179.43 (18)
C3—C2—C8—C7	109.8 (2)	C23—O3—C22—O2	0.8 (3)
C1—C2—C8—C7	−66.9 (2)	C23—O3—C22—C19	178.95 (17)
C3—C2—C8—C9	−128.8 (2)	C20—C19—C22—O2	177.1 (2)
C1—C2—C8—C9	54.5 (2)	C18—C19—C22—O2	−0.6 (3)
C5—C4—C11—C14	176.14 (18)	C20—C19—C22—O3	−1.0 (3)
C3—C4—C11—C14	−2.1 (3)	C18—C19—C22—O3	−178.74 (18)
C5—C4—C11—C13	56.0 (2)	C22—O3—C23—C24	−173.52 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.87 (1)	1.80 (2)	2.609 (2)	154 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.87 (1)	1.80 (2)	2.609 (2)	154 (3)