(E)-2-[4-tert-Butyl-5-(2,4,5-trimethoxy-benz-yl)thia-zol-2-ylimino-meth-yl]phenol.

In the title compound, C(24)H(28)N(2)O(4)S, the dihedral angle between the phenol ring and the thia-zole ring system is 10.6 (1)°, and the trimethoxy-phenyl group is approximately perpendicular to the thia-zole ring, the dihedral angle being 84.7 (2)°. There is a strong intra-molecular hydrogen-bonding inter-action between the Schiff base and the hydr-oxy group.

Related literature

For general background, see: Modi et al. (1971 ▶); More et al. (2001 ▶).

Experimental

Crystal data

C24H28N2O4S

M = 440.54

Triclinic,

a = 10.9137 (6) Å

b = 11.0904 (6) Å

c = 11.1260 (6) Å

α = 64.933 (1)°

β = 72.383 (1)°

γ = 83.202 (1)°

V = 1162.54 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 293 (2) K

0.48 × 0.44 × 0.42 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.922, T max = 0.932

9103 measured reflections

4524 independent reflections

3450 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.131

S = 1.05

4524 reflections

287 parameters

24 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2005 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063921/sg2213sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063921/sg2213Isup2.hkl

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

C24H28N2O4S	Z = 2
Mr = 440.54	F000 = 468
Triclinic, P1	Dx = 1.259 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.9137 (6) Å	Cell parameters from 4266 reflections
b = 11.0904 (6) Å	θ = 2.3–26.9º
c = 11.1260 (6) Å	µ = 0.17 mm−1
α = 64.933 (1)º	T = 293 (2) K
β = 72.383 (1)º	Block, yellow
γ = 83.202 (1)º	0.48 × 0.44 × 0.42 mm
V = 1162.54 (11) Å3

Bruker SMART 1K CCD diffractometer	4524 independent reflections
Radiation source: fine-focus sealed tube	3450 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 293(2) K	θmax = 26.0º
ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −13→13
Tmin = 0.922, Tmax = 0.932	k = −13→13
9103 measured reflections	l = −13→13

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0538P)2 + 0.4082P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4524 reflections	Δρmax = 0.24 e Å−3
287 parameters	Δρmin = −0.16 e Å−3
24 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. Spectroscopic analysis: 1H-NMR (CDCl3, 400 MHz) (p.p.m.): 1.48(s, 9H, (CH3)3), 3.80, 3.82, 3.91(3×s, 9H, 3×CH3O), 4.19(s, 2H, CH2), 6.55, 6.69(2×s, 2H, 2,4,5-(OCH3)3C6H2), 6.93(dd, J = 8.0 Hz, J= 8.0 Hz, 1H, 2-HOC6H45-H), 6.99(d, J= 8.0 Hz, 1H, 2-HOC6H43-H), 7.39(ddd, J = 8.0 Hz, J = 8.0 Hz, J = 1.6 Hz, 1H, 2-HOC6H44-H), 7.42(dd, J = 8.0 Hz, J = 1.6 Hz, 1H, 2-HOC6H46-H), 9.02(s, 1H, N=CH), 12.32(s, 1H, OH).

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.

	x	y	z	Uiso*/Ueq
S1	0.63017 (5)	0.60302 (5)	0.32907 (5)	0.05115 (17)
C1	0.52224 (18)	0.72677 (19)	0.33490 (19)	0.0465 (4)
C2	0.59138 (19)	0.6896 (2)	0.5140 (2)	0.0488 (5)
C3	0.66530 (17)	0.59963 (19)	0.47095 (18)	0.0445 (4)
C4	0.39884 (19)	0.8906 (2)	0.2148 (2)	0.0511 (5)
H4	0.3968	0.9315	0.2731	0.061*
C5	0.33379 (19)	0.9527 (2)	0.1080 (2)	0.0502 (5)
C6	0.3394 (2)	0.9001 (2)	0.0126 (2)	0.0556 (5)
C7	0.2783 (2)	0.9653 (3)	−0.0905 (2)	0.0715 (7)
H7	0.2832	0.9316	−0.1554	0.086*
C8	0.2110 (2)	1.0789 (3)	−0.0969 (3)	0.0781 (7)
H8	0.1704	1.1215	−0.1663	0.094*
C9	0.2023 (3)	1.1309 (3)	−0.0031 (3)	0.0786 (7)
H9	0.1552	1.2075	−0.0077	0.094*
C10	0.2638 (2)	1.0689 (2)	0.0975 (3)	0.0677 (6)
H10	0.2589	1.1050	0.1605	0.081*
C11	0.5924 (3)	0.7197 (3)	0.6354 (2)	0.0701 (6)
C12	0.4742 (4)	0.7988 (4)	0.6703 (3)	0.1338 (15)
H12A	0.4741	0.8808	0.5914	0.201*
H12B	0.4755	0.8177	0.7465	0.201*
H12C	0.3983	0.7479	0.6951	0.201*
C13	0.7146 (4)	0.7995 (4)	0.5940 (4)	0.1271 (13)
H13A	0.7884	0.7490	0.5703	0.191*
H13B	0.7181	0.8176	0.6700	0.191*
H13C	0.7140	0.8819	0.5157	0.191*
C14	0.5886 (3)	0.5915 (3)	0.7651 (2)	0.0854 (8)
H14A	0.5159	0.5380	0.7854	0.128*
H14B	0.5814	0.6133	0.8417	0.128*
H14C	0.6662	0.5427	0.7495	0.128*
C15	0.76608 (18)	0.5036 (2)	0.5243 (2)	0.0509 (5)
H15A	0.8073	0.5396	0.5681	0.061*
H15B	0.7246	0.4202	0.5939	0.061*
C16	0.86707 (18)	0.4771 (2)	0.4116 (2)	0.0496 (5)
C17	0.95846 (18)	0.5741 (2)	0.3172 (2)	0.0519 (5)
C18	1.0483 (2)	0.5553 (3)	0.2080 (2)	0.0637 (6)
H18	1.1078	0.6221	0.1439	0.076*
C19	1.0488 (2)	0.4373 (3)	0.1951 (3)	0.0732 (7)
C20	0.9608 (3)	0.3373 (3)	0.2909 (3)	0.0752 (7)
C21	0.8698 (2)	0.3587 (2)	0.3973 (2)	0.0625 (6)
H21	0.8094	0.2924	0.4603	0.075*
C22	1.0551 (2)	0.7806 (2)	0.2629 (3)	0.0811 (8)
H22A	1.1336	0.7361	0.2775	0.122*
H22B	1.0411	0.8510	0.2941	0.122*
H22C	1.0608	0.8173	0.1662	0.122*
C23	1.2105 (3)	0.5148 (4)	−0.0208 (3)	0.1211 (13)
H23A	1.1569	0.5858	−0.0623	0.182*
H23B	1.2617	0.4832	−0.0883	0.182*
H23C	1.2658	0.5469	0.0121	0.182*
C24	0.8942 (5)	0.1181 (4)	0.3630 (6)	0.1547 (19)
H24A	0.9150	0.0846	0.4494	0.232*
H24B	0.9070	0.0496	0.3294	0.232*
H24C	0.8061	0.1453	0.3764	0.232*
N1	0.51002 (16)	0.76202 (17)	0.43512 (16)	0.0512 (4)
N2	0.45913 (15)	0.78106 (17)	0.23124 (16)	0.0501 (4)
O1	0.40160 (19)	0.78624 (19)	0.01767 (18)	0.0806 (5)
H1	0.4365	0.7590	0.0800	0.121*
O2	0.95144 (14)	0.68869 (15)	0.33783 (16)	0.0659 (4)
O3	1.1324 (2)	0.4094 (3)	0.0912 (2)	0.1084 (7)
O4	0.9706 (3)	0.2228 (3)	0.2707 (3)	0.1280 (9)

	U11	U22	U33	U12	U13	U23
S1	0.0522 (3)	0.0601 (3)	0.0439 (3)	0.0063 (2)	−0.0152 (2)	−0.0243 (2)
C1	0.0443 (10)	0.0521 (11)	0.0390 (10)	−0.0018 (8)	−0.0105 (8)	−0.0152 (8)
C2	0.0509 (11)	0.0518 (11)	0.0431 (10)	0.0017 (9)	−0.0144 (9)	−0.0184 (9)
C3	0.0404 (9)	0.0503 (10)	0.0389 (9)	−0.0028 (8)	−0.0095 (8)	−0.0150 (8)
C4	0.0526 (11)	0.0547 (12)	0.0458 (11)	−0.0039 (9)	−0.0146 (9)	−0.0187 (9)
C5	0.0462 (10)	0.0526 (11)	0.0457 (10)	−0.0030 (9)	−0.0130 (8)	−0.0135 (9)
C6	0.0506 (11)	0.0651 (13)	0.0473 (11)	0.0059 (10)	−0.0158 (9)	−0.0195 (10)
C7	0.0700 (15)	0.0908 (18)	0.0557 (13)	0.0123 (13)	−0.0288 (12)	−0.0274 (13)
C8	0.0658 (15)	0.0885 (19)	0.0678 (15)	0.0092 (14)	−0.0341 (13)	−0.0122 (14)
C9	0.0777 (17)	0.0661 (15)	0.0836 (18)	0.0169 (13)	−0.0337 (14)	−0.0194 (14)
C10	0.0745 (15)	0.0587 (13)	0.0707 (15)	0.0070 (11)	−0.0277 (12)	−0.0240 (12)
C11	0.0889 (17)	0.0793 (16)	0.0610 (14)	0.0212 (13)	−0.0340 (12)	−0.0425 (12)
C12	0.185 (3)	0.166 (3)	0.097 (2)	0.108 (3)	−0.078 (2)	−0.098 (2)
C13	0.174 (3)	0.130 (3)	0.116 (3)	−0.041 (3)	−0.054 (3)	−0.067 (2)
C14	0.100 (2)	0.112 (2)	0.0506 (13)	0.0261 (16)	−0.0310 (13)	−0.0392 (14)
C15	0.0459 (10)	0.0548 (11)	0.0438 (10)	0.0023 (9)	−0.0125 (8)	−0.0130 (9)
C16	0.0422 (10)	0.0548 (11)	0.0469 (11)	0.0054 (9)	−0.0157 (8)	−0.0153 (9)
C17	0.0420 (10)	0.0581 (12)	0.0516 (11)	0.0053 (9)	−0.0159 (9)	−0.0181 (10)
C18	0.0456 (11)	0.0832 (16)	0.0547 (13)	0.0020 (11)	−0.0095 (10)	−0.0245 (12)
C19	0.0590 (14)	0.104 (2)	0.0664 (15)	0.0146 (14)	−0.0160 (12)	−0.0484 (15)
C20	0.0733 (16)	0.0789 (17)	0.0897 (18)	0.0105 (13)	−0.0240 (14)	−0.0513 (15)
C21	0.0590 (13)	0.0573 (13)	0.0682 (14)	0.0010 (10)	−0.0163 (11)	−0.0241 (11)
C22	0.0606 (14)	0.0619 (15)	0.099 (2)	−0.0083 (12)	−0.0180 (14)	−0.0138 (14)
C23	0.084 (2)	0.209 (4)	0.074 (2)	0.005 (2)	0.0011 (17)	−0.077 (3)
C24	0.153 (4)	0.088 (3)	0.252 (6)	0.015 (3)	−0.062 (4)	−0.097 (3)
N1	0.0518 (9)	0.0570 (10)	0.0465 (9)	0.0069 (8)	−0.0162 (7)	−0.0228 (8)
N2	0.0473 (9)	0.0575 (10)	0.0437 (9)	0.0004 (8)	−0.0152 (7)	−0.0173 (8)
O1	0.0993 (13)	0.0948 (13)	0.0727 (11)	0.0399 (10)	−0.0488 (10)	−0.0505 (10)
O2	0.0539 (9)	0.0601 (9)	0.0748 (10)	−0.0058 (7)	−0.0072 (7)	−0.0250 (8)
O3	0.0873 (14)	0.157 (2)	0.0968 (15)	0.0142 (14)	−0.0022 (12)	−0.0863 (16)
O4	0.133 (2)	0.1112 (18)	0.165 (2)	0.0027 (15)	−0.0126 (17)	−0.1002 (19)

S1—C1	1.709 (2)	C14—H14A	0.9600
S1—C3	1.7184 (19)	C14—H14B	0.9600
C1—N1	1.297 (2)	C14—H14C	0.9600
C1—N2	1.400 (2)	C15—C16	1.507 (3)
C2—C3	1.363 (3)	C15—H15A	0.9700
C2—N1	1.382 (2)	C15—H15B	0.9700
C2—C11	1.525 (3)	C16—C21	1.384 (3)
C3—C15	1.509 (3)	C16—C17	1.385 (3)
C4—N2	1.280 (3)	C17—O2	1.373 (3)
C4—C5	1.446 (3)	C17—C18	1.388 (3)
C4—H4	0.9300	C18—C19	1.375 (3)
C5—C6	1.396 (3)	C18—H18	0.9300
C5—C10	1.397 (3)	C19—O3	1.365 (3)
C6—O1	1.349 (3)	C19—C20	1.386 (4)
C6—C7	1.389 (3)	C20—O4	1.367 (3)
C7—C8	1.367 (3)	C20—C21	1.384 (3)
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.367 (4)	C22—O2	1.413 (3)
C8—H8	0.9300	C22—H22A	0.9600
C9—C10	1.367 (3)	C22—H22B	0.9600
C9—H9	0.9300	C22—H22C	0.9600
C10—H10	0.9300	C23—O3	1.416 (4)
C11—C12	1.517 (4)	C23—H23A	0.9600
C11—C13	1.529 (4)	C23—H23B	0.9600
C11—C14	1.532 (4)	C23—H23C	0.9600
C12—H12A	0.9600	C24—O4	1.341 (5)
C12—H12B	0.9600	C24—H24A	0.9600
C12—H12C	0.9600	C24—H24B	0.9600
C13—H13A	0.9600	C24—H24C	0.9600
C13—H13B	0.9600	O1—H1	0.8200
C13—H13C	0.9600
C1—S1—C3	89.45 (9)	C11—C14—H14C	109.5
N1—C1—N2	127.00 (18)	H14A—C14—H14C	109.5
N1—C1—S1	115.35 (14)	H14B—C14—H14C	109.5
N2—C1—S1	117.64 (14)	C16—C15—C3	112.66 (16)
C3—C2—N1	114.89 (17)	C16—C15—H15A	109.1
C3—C2—C11	127.01 (18)	C3—C15—H15A	109.1
N1—C2—C11	118.08 (18)	C16—C15—H15B	109.1
C2—C3—C15	132.31 (18)	C3—C15—H15B	109.1
C2—C3—S1	109.68 (14)	H15A—C15—H15B	107.8
C15—C3—S1	118.01 (14)	C21—C16—C17	118.45 (19)
N2—C4—C5	121.83 (19)	C21—C16—C15	121.81 (19)
N2—C4—H4	119.1	C17—C16—C15	119.72 (19)
C5—C4—H4	119.1	O2—C17—C16	115.65 (18)
C6—C5—C10	118.15 (19)	O2—C17—C18	123.3 (2)
C6—C5—C4	121.68 (19)	C16—C17—C18	121.0 (2)
C10—C5—C4	120.2 (2)	C19—C18—C17	119.6 (2)
O1—C6—C7	118.3 (2)	C19—C18—H18	120.2
O1—C6—C5	122.07 (18)	C17—C18—H18	120.2
C7—C6—C5	119.6 (2)	O3—C19—C18	124.1 (3)
C8—C7—C6	120.2 (2)	O3—C19—C20	115.6 (3)
C8—C7—H7	119.9	C18—C19—C20	120.3 (2)
C6—C7—H7	119.9	O4—C20—C21	124.6 (3)
C9—C8—C7	121.2 (2)	O4—C20—C19	115.9 (2)
C9—C8—H8	119.4	C21—C20—C19	119.4 (2)
C7—C8—H8	119.4	C20—C21—C16	121.2 (2)
C8—C9—C10	119.1 (2)	C20—C21—H21	119.4
C8—C9—H9	120.4	C16—C21—H21	119.4
C10—C9—H9	120.4	O2—C22—H22A	109.5
C9—C10—C5	121.7 (2)	O2—C22—H22B	109.5
C9—C10—H10	119.2	H22A—C22—H22B	109.5
C5—C10—H10	119.2	O2—C22—H22C	109.5
C12—C11—C2	109.8 (2)	H22A—C22—H22C	109.5
C12—C11—C13	110.4 (3)	H22B—C22—H22C	109.5
C2—C11—C13	108.1 (2)	O3—C23—H23A	109.5
C12—C11—C14	107.2 (2)	O3—C23—H23B	109.5
C2—C11—C14	111.3 (2)	H23A—C23—H23B	109.5
C13—C11—C14	110.0 (2)	O3—C23—H23C	109.5
C11—C12—H12A	109.5	H23A—C23—H23C	109.5
C11—C12—H12B	109.5	H23B—C23—H23C	109.5
H12A—C12—H12B	109.5	O4—C24—H24A	109.5
C11—C12—H12C	109.5	O4—C24—H24B	109.5
H12A—C12—H12C	109.5	H24A—C24—H24B	109.5
H12B—C12—H12C	109.5	O4—C24—H24C	109.5
C11—C13—H13A	109.5	H24A—C24—H24C	109.5
C11—C13—H13B	109.5	H24B—C24—H24C	109.5
H13A—C13—H13B	109.5	C1—N1—C2	110.61 (17)
C11—C13—H13C	109.5	C4—N2—C1	119.30 (17)
H13A—C13—H13C	109.5	C6—O1—H1	109.5
H13B—C13—H13C	109.5	C17—O2—C22	118.54 (18)
C11—C14—H14A	109.5	C19—O3—C23	117.8 (3)
C11—C14—H14B	109.5	C24—O4—C20	119.8 (3)
H14A—C14—H14B	109.5
C3—S1—C1—N1	−1.29 (16)	C3—C15—C16—C17	73.2 (2)
C3—S1—C1—N2	177.33 (15)	C21—C16—C17—O2	−179.37 (18)
N1—C2—C3—C15	179.01 (18)	C15—C16—C17—O2	2.1 (3)
C11—C2—C3—C15	0.7 (4)	C21—C16—C17—C18	2.1 (3)
N1—C2—C3—S1	−1.1 (2)	C15—C16—C17—C18	−176.49 (18)
C11—C2—C3—S1	−179.50 (18)	O2—C17—C18—C19	179.9 (2)
C1—S1—C3—C2	1.31 (15)	C16—C17—C18—C19	−1.7 (3)
C1—S1—C3—C15	−178.82 (15)	C17—C18—C19—O3	179.6 (2)
N2—C4—C5—C6	−3.6 (3)	C17—C18—C19—C20	−0.4 (4)
N2—C4—C5—C10	176.90 (19)	O3—C19—C20—O4	1.3 (4)
C10—C5—C6—O1	−178.0 (2)	C18—C19—C20—O4	−178.8 (2)
C4—C5—C6—O1	2.4 (3)	O3—C19—C20—C21	−178.0 (2)
C10—C5—C6—C7	1.3 (3)	C18—C19—C20—C21	2.0 (4)
C4—C5—C6—C7	−178.2 (2)	O4—C20—C21—C16	179.3 (3)
O1—C6—C7—C8	178.1 (2)	C19—C20—C21—C16	−1.6 (4)
C5—C6—C7—C8	−1.3 (4)	C17—C16—C21—C20	−0.4 (3)
C6—C7—C8—C9	0.1 (4)	C15—C16—C21—C20	178.1 (2)
C7—C8—C9—C10	1.0 (4)	N2—C1—N1—C2	−177.61 (18)
C8—C9—C10—C5	−0.9 (4)	S1—C1—N1—C2	0.9 (2)
C6—C5—C10—C9	−0.2 (3)	C3—C2—N1—C1	0.2 (2)
C4—C5—C10—C9	179.3 (2)	C11—C2—N1—C1	178.72 (19)
C3—C2—C11—C12	−165.6 (3)	C5—C4—N2—C1	178.90 (17)
N1—C2—C11—C12	16.0 (3)	N1—C1—N2—C4	12.8 (3)
C3—C2—C11—C13	73.8 (3)	S1—C1—N2—C4	−165.62 (15)
N1—C2—C11—C13	−104.5 (3)	C16—C17—O2—C22	168.02 (19)
C3—C2—C11—C14	−47.1 (3)	C18—C17—O2—C22	−13.5 (3)
N1—C2—C11—C14	134.6 (2)	C18—C19—O3—C23	−9.7 (4)
C2—C3—C15—C16	−150.2 (2)	C20—C19—O3—C23	170.2 (3)
S1—C3—C15—C16	30.0 (2)	C21—C20—O4—C24	−4.7 (5)
C3—C15—C16—C21	−105.3 (2)	C19—C20—O4—C24	176.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.89	2.612 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.82	1.89	2.612 (2)	147