(E)-4-Bromo-2-[(2,6-diisopropyl-phen-yl)imino-meth-yl]phenol.

In the title compound, C(19)H(22)BrNO, the dihedral angle between the benzene rings is 76.17 (14)° and an intra-molecular O-H⋯N hydrogen bond with an S(6) graph-set motif is present. One methyl group is disordered over two sets of sites with site occupancies of 0.66 (3) and 0.34 (3). A weak inter-molecular C-H⋯π inter-action is observed in the crystal structure.

Related literature

For the biological activity of Schiff base ligands, see: Daier et al. (2004 ▶); Santos et al. (2001 ▶). For related structures, see: Raja et al. (2008 ▶); Lin et al. (2005 ▶).

Experimental

Crystal data

C19H22BrNO

M = 360.29

Orthorhombic,

a = 6.1851 (12) Å

b = 12.759 (3) Å

c = 22.698 (5) Å

V = 1791.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.30 mm−1

T = 295 K

0.24 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.609, T max = 0.683

23590 measured reflections

5107 independent reflections

3242 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.100

S = 1.01

5107 reflections

214 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 2179 Friedel pairs

Flack parameter: 0.011 (10)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021605/is5140sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021605/is5140Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021605/is5140Isup3.cml

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

C19H22BrNO	F(000) = 744
Mr = 360.29	Dx = 1.336 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2359 reflections
a = 6.1851 (12) Å	θ = 1.8–29.8°
b = 12.759 (3) Å	µ = 2.30 mm−1
c = 22.698 (5) Å	T = 295 K
V = 1791.3 (6) Å3	Prism, light yellow
Z = 4	0.24 × 0.22 × 0.18 mm

Bruker Kappa APEXII diffractometer	5107 independent reflections
Radiation source: fine-focus sealed tube	3242 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω and φ scans	θmax = 29.8°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.609, Tmax = 0.683	k = −17→11
23590 measured reflections	l = −30→31

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.1641P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
5107 reflections	Δρmax = 0.38 e Å−3
214 parameters	Δρmin = −0.22 e Å−3
0 restraints	Absolute structure: Flack (1983), 2179 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.011 (10)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.52689 (6)	0.49239 (2)	0.950698 (17)	0.07970 (14)
O1	1.1558 (3)	0.14355 (16)	0.90753 (9)	0.0593 (5)
H1	1.1027	0.0973	0.8870	0.089*
N1	0.8534 (3)	0.04639 (16)	0.84992 (9)	0.0439 (5)
C1	0.7847 (4)	−0.0403 (2)	0.81528 (12)	0.0454 (6)
C2	0.6525 (5)	−0.1178 (2)	0.83940 (14)	0.0579 (7)
C3	0.6048 (6)	−0.2032 (2)	0.80436 (16)	0.0747 (10)
H3	0.5181	−0.2565	0.8192	0.090*
C4	0.6846 (7)	−0.2105 (3)	0.74734 (17)	0.0814 (11)
H4	0.6517	−0.2690	0.7246	0.098*
C5	0.8084 (6)	−0.1344 (3)	0.72451 (16)	0.0736 (10)
H5	0.8562	−0.1399	0.6858	0.088*
C6	0.8666 (5)	−0.0472 (2)	0.75789 (13)	0.0542 (7)
C7	0.5681 (6)	−0.1119 (2)	0.90207 (15)	0.0744 (10)
H7	0.5856	−0.0393	0.9154	0.089*
C8	0.7009 (9)	−0.1799 (5)	0.94217 (19)	0.1273 (19)
H8A	0.6944	−0.2512	0.9288	0.191*
H8B	0.6448	−0.1756	0.9815	0.191*
H8C	0.8483	−0.1563	0.9418	0.191*
C9	0.3341 (7)	−0.1387 (5)	0.9075 (2)	0.1205 (18)
H9A	0.2865	−0.1250	0.9470	0.181*
H9B	0.3135	−0.2115	0.8986	0.181*
H9C	0.2519	−0.0968	0.8805	0.181*
C10	1.0109 (5)	0.0367 (2)	0.73253 (13)	0.0632 (7)
H10A	1.0195	0.0961	0.7598	0.076*	0.66 (3)
H10B	1.0424	0.0756	0.7688	0.076*	0.34 (3)
C11	0.933 (2)	0.0755 (10)	0.6705 (6)	0.097 (3)	0.66 (3)
H11A	0.7786	0.0838	0.6708	0.145*	0.66 (3)
H11B	0.9724	0.0249	0.6411	0.145*	0.66 (3)
H11C	0.9998	0.1415	0.6616	0.145*	0.66 (3)
C11A	0.884 (2)	0.114 (2)	0.7024 (16)	0.090 (8)	0.34 (3)
H11D	0.9780	0.1663	0.6856	0.135*	0.34 (3)
H11E	0.7874	0.1474	0.7299	0.135*	0.34 (3)
H11F	0.8016	0.0816	0.6717	0.135*	0.34 (3)
C12	1.2339 (6)	−0.0035 (5)	0.7194 (3)	0.1209 (16)
H12A	1.2247	−0.0607	0.6920	0.181*
H12B	1.3004	−0.0274	0.7552	0.181*
H12C	1.3193	0.0518	0.7026	0.181*
C13	0.7284 (4)	0.12241 (19)	0.86014 (11)	0.0422 (6)
H13	0.5887	0.1212	0.8450	0.051*
C14	0.7982 (4)	0.21236 (17)	0.89527 (10)	0.0384 (5)
C15	1.0081 (4)	0.21757 (17)	0.91771 (10)	0.0422 (5)
C16	1.0655 (4)	0.3034 (2)	0.95214 (12)	0.0512 (6)
H16	1.2027	0.3063	0.9688	0.061*
C17	0.9235 (4)	0.38342 (19)	0.96183 (12)	0.0524 (7)
H17	0.9646	0.4406	0.9846	0.063*
C18	0.7203 (5)	0.37927 (19)	0.93793 (12)	0.0503 (6)
C19	0.6555 (4)	0.29447 (18)	0.90542 (11)	0.0451 (6)
H19	0.5161	0.2919	0.8902	0.054*

	U11	U22	U33	U12	U13	U23
Br1	0.0866 (2)	0.04417 (15)	0.1083 (3)	0.00809 (16)	−0.00202 (19)	−0.02501 (15)
O1	0.0492 (10)	0.0627 (12)	0.0659 (13)	0.0044 (9)	−0.0119 (9)	−0.0171 (10)
N1	0.0484 (12)	0.0408 (10)	0.0425 (12)	0.0010 (9)	−0.0039 (10)	−0.0101 (9)
C1	0.0501 (14)	0.0390 (12)	0.0471 (15)	0.0059 (10)	−0.0079 (12)	−0.0103 (11)
C2	0.0687 (19)	0.0389 (13)	0.0662 (19)	−0.0029 (13)	−0.0054 (16)	−0.0082 (13)
C3	0.098 (3)	0.0426 (15)	0.083 (2)	−0.0111 (16)	−0.005 (2)	−0.0158 (16)
C4	0.107 (3)	0.0502 (17)	0.087 (3)	−0.0003 (18)	−0.020 (2)	−0.0313 (17)
C5	0.094 (3)	0.069 (2)	0.058 (2)	0.0120 (19)	−0.0027 (19)	−0.0291 (17)
C6	0.0587 (16)	0.0519 (14)	0.0520 (17)	0.0123 (13)	−0.0015 (14)	−0.0127 (13)
C7	0.108 (3)	0.0476 (15)	0.067 (2)	−0.0152 (18)	0.014 (2)	−0.0056 (15)
C8	0.107 (3)	0.197 (6)	0.078 (3)	−0.001 (4)	−0.007 (3)	0.025 (3)
C9	0.091 (3)	0.148 (5)	0.123 (4)	0.008 (3)	0.032 (3)	0.000 (3)
C10	0.0646 (18)	0.0675 (16)	0.0575 (16)	0.0092 (15)	0.0088 (15)	−0.0125 (13)
C11	0.099 (6)	0.106 (6)	0.085 (6)	0.019 (5)	0.003 (5)	0.024 (5)
C11A	0.070 (8)	0.087 (11)	0.114 (18)	0.003 (7)	0.011 (8)	0.043 (12)
C12	0.084 (2)	0.109 (3)	0.170 (5)	0.012 (3)	0.032 (3)	0.001 (4)
C13	0.0442 (14)	0.0415 (12)	0.0408 (15)	−0.0048 (11)	−0.0065 (11)	−0.0051 (11)
C14	0.0465 (13)	0.0362 (11)	0.0326 (12)	−0.0048 (10)	0.0028 (10)	−0.0024 (10)
C15	0.0466 (14)	0.0435 (11)	0.0364 (12)	−0.0054 (12)	−0.0005 (12)	−0.0017 (9)
C16	0.0529 (14)	0.0573 (14)	0.0435 (14)	−0.0130 (11)	−0.0068 (13)	−0.0046 (12)
C17	0.0686 (18)	0.0429 (12)	0.0458 (15)	−0.0169 (12)	−0.0014 (13)	−0.0108 (11)
C18	0.0628 (16)	0.0340 (11)	0.0541 (17)	−0.0041 (11)	0.0033 (13)	−0.0071 (11)
C19	0.0499 (14)	0.0396 (12)	0.0457 (14)	−0.0035 (11)	−0.0014 (12)	−0.0061 (11)

Br1—C18	1.897 (3)	C10—C11A	1.438 (13)
O1—C15	1.334 (3)	C10—C12	1.502 (5)
O1—H1	0.8200	C10—C11	1.569 (9)
N1—C13	1.262 (3)	C10—H10A	0.9800
N1—C1	1.422 (3)	C10—H10B	0.9800
C1—C2	1.394 (4)	C11—H11A	0.9600
C1—C6	1.401 (4)	C11—H11B	0.9600
C2—C3	1.381 (4)	C11—H11C	0.9600
C2—C7	1.517 (5)	C11A—H11D	0.9600
C3—C4	1.388 (5)	C11A—H11E	0.9600
C3—H3	0.9300	C11A—H11F	0.9600
C4—C5	1.340 (5)	C12—H12A	0.9600
C4—H4	0.9300	C12—H12B	0.9600
C5—C6	1.393 (4)	C12—H12C	0.9600
C5—H5	0.9300	C13—C14	1.462 (3)
C6—C10	1.508 (4)	C13—H13	0.9300
C7—C9	1.492 (6)	C14—C19	1.389 (3)
C7—C8	1.502 (6)	C14—C15	1.396 (4)
C7—H7	0.9800	C15—C16	1.392 (3)
C8—H8A	0.9600	C16—C17	1.364 (4)
C8—H8B	0.9600	C16—H16	0.9300
C8—H8C	0.9600	C17—C18	1.370 (4)
C9—H9A	0.9600	C17—H17	0.9300
C9—H9B	0.9600	C18—C19	1.370 (3)
C9—H9C	0.9600	C19—H19	0.9300
C15—O1—H1	109.5	C12—C10—H10A	109.9
C13—N1—C1	121.1 (2)	C6—C10—H10A	109.9
C2—C1—C6	122.2 (3)	C11—C10—H10A	109.9
C2—C1—N1	120.6 (2)	C11A—C10—H10B	99.1
C6—C1—N1	117.1 (2)	C12—C10—H10B	99.0
C3—C2—C1	117.3 (3)	C6—C10—H10B	99.0
C3—C2—C7	120.4 (3)	C10—C11—H11A	109.5
C1—C2—C7	122.3 (2)	C10—C11—H11B	109.5
C2—C3—C4	120.9 (3)	C10—C11—H11C	109.5
C2—C3—H3	119.5	C10—C11A—H11D	109.5
C4—C3—H3	119.5	C10—C11A—H11E	109.5
C5—C4—C3	121.0 (3)	H11D—C11A—H11E	109.5
C5—C4—H4	119.5	C10—C11A—H11F	109.5
C3—C4—H4	119.5	H11D—C11A—H11F	109.5
C4—C5—C6	121.0 (3)	H11E—C11A—H11F	109.5
C4—C5—H5	119.5	C10—C12—H12A	109.5
C6—C5—H5	119.5	C10—C12—H12B	109.5
C5—C6—C1	117.6 (3)	H12A—C12—H12B	109.5
C5—C6—C10	120.8 (3)	C10—C12—H12C	109.5
C1—C6—C10	121.6 (2)	H12A—C12—H12C	109.5
C9—C7—C8	110.3 (4)	H12B—C12—H12C	109.5
C9—C7—C2	113.6 (3)	N1—C13—C14	121.5 (2)
C8—C7—C2	110.6 (3)	N1—C13—H13	119.2
C9—C7—H7	107.3	C14—C13—H13	119.2
C8—C7—H7	107.3	C19—C14—C15	119.6 (2)
C2—C7—H7	107.3	C19—C14—C13	119.7 (2)
C7—C8—H8A	109.5	C15—C14—C13	120.7 (2)
C7—C8—H8B	109.5	O1—C15—C16	118.7 (2)
H8A—C8—H8B	109.5	O1—C15—C14	122.7 (2)
C7—C8—H8C	109.5	C16—C15—C14	118.6 (2)
H8A—C8—H8C	109.5	C17—C16—C15	121.0 (2)
H8B—C8—H8C	109.5	C17—C16—H16	119.5
C7—C9—H9A	109.5	C15—C16—H16	119.5
C7—C9—H9B	109.5	C16—C17—C18	119.8 (2)
H9A—C9—H9B	109.5	C16—C17—H17	120.1
C7—C9—H9C	109.5	C18—C17—H17	120.1
H9A—C9—H9C	109.5	C19—C18—C17	120.8 (2)
H9B—C9—H9C	109.5	C19—C18—Br1	119.9 (2)
C11A—C10—C12	130.0 (11)	C17—C18—Br1	119.25 (19)
C11A—C10—C6	110.4 (6)	C18—C19—C14	120.0 (3)
C12—C10—C6	112.1 (3)	C18—C19—H19	120.0
C12—C10—C11	102.2 (7)	C14—C19—H19	120.0
C6—C10—C11	112.6 (4)
C13—N1—C1—C2	−78.3 (3)	C1—C6—C10—C11A	−91.3 (18)
C13—N1—C1—C6	105.7 (3)	C5—C6—C10—C12	−65.0 (4)
C6—C1—C2—C3	0.3 (4)	C1—C6—C10—C12	115.6 (4)
N1—C1—C2—C3	−175.6 (3)	C5—C6—C10—C11	49.7 (8)
C6—C1—C2—C7	178.4 (3)	C1—C6—C10—C11	−129.7 (8)
N1—C1—C2—C7	2.6 (4)	C1—N1—C13—C14	−179.5 (2)
C1—C2—C3—C4	−0.5 (5)	N1—C13—C14—C19	179.9 (2)
C7—C2—C3—C4	−178.7 (3)	N1—C13—C14—C15	1.2 (4)
C2—C3—C4—C5	−0.6 (6)	C19—C14—C15—O1	−177.2 (2)
C3—C4—C5—C6	2.1 (6)	C13—C14—C15—O1	1.5 (4)
C4—C5—C6—C1	−2.2 (5)	C19—C14—C15—C16	2.9 (3)
C4—C5—C6—C10	178.3 (3)	C13—C14—C15—C16	−178.4 (2)
C2—C1—C6—C5	1.1 (4)	O1—C15—C16—C17	177.2 (2)
N1—C1—C6—C5	177.1 (3)	C14—C15—C16—C17	−2.8 (4)
C2—C1—C6—C10	−179.5 (3)	C15—C16—C17—C18	0.6 (4)
N1—C1—C6—C10	−3.5 (4)	C16—C17—C18—C19	1.5 (4)
C3—C2—C7—C9	−46.7 (5)	C16—C17—C18—Br1	−178.9 (2)
C1—C2—C7—C9	135.2 (4)	C17—C18—C19—C14	−1.4 (4)
C3—C2—C7—C8	78.0 (4)	Br1—C18—C19—C14	178.98 (19)
C1—C2—C7—C8	−100.1 (4)	C15—C14—C19—C18	−0.8 (4)
C5—C6—C10—C11A	88.1 (18)	C13—C14—C19—C18	−179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.597 (3)	147
C16—H16···Cg2i	0.93	2.86	3.522 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.597 (3)	147
C16—H16⋯Cg2i	0.93	2.86	3.522 (3)	129

Symmetry code: (i) .