N'-[(1E)-3-Bromo-5-chloro-2-hy-droxy-benzyl-idene]-4-tert-butyl-benzo-hydrazide ethanol monosolvate.

In the title compound, C(18)H(18)BrClN(2)O(2)·C(2)H(6)O, the hy-droxy group forms an intra-molecular O-H⋯N hydrogen bond, which influences the conformation of the Shiff base mol-ecule, where the two aromatic rings form a dihedral angle of 21.67 (8)°. Inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link two Shiff base mol-ecules and two solvent mol-ecules into a centrosymmetric heterotetra-mer. Weak inter-molecular C-H⋯O inter-actions link further tetra-mers related by translation along the a axis into chains.

Related literature

For the biological activity of Schiff base derivatives, see: Dao et al. (2000 ▶); Karthikeyan et al. (2006 ▶); Prabhakaran et al. (2006 ▶); Shivakumar et al. (2008 ▶). For related structures, see: Fun et al. (2008 ▶); Thirugnanasundar et al. (2011 ▶).

Experimental

Crystal data

C18H18BrClN2O2·C2H6O

M = 455.77

Triclinic,

a = 9.2478 (4) Å

b = 9.4057 (4) Å

c = 12.7838 (5) Å

α = 78.811 (2)°

β = 79.235 (1)°

γ = 79.469 (2)°

V = 1059.17 (8) Å3

Z = 2

Mo Kα radiation

μ = 2.09 mm−1

T = 295 K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.613, T max = 0.680

27712 measured reflections

6728 independent reflections

3460 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.180

S = 1.03

6728 reflections

248 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.63 e Å−3

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/S160053681104027X/cv5157sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104027X/cv5157Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104027X/cv5157Isup3.cml

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

C18H18BrClN2O2·C2H6O	Z = 2
Mr = 455.77	F(000) = 468
Triclinic, P1	Dx = 1.429 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2478 (4) Å	Cell parameters from 5983 reflections
b = 9.4057 (4) Å	θ = 2.2–25.3°
c = 12.7838 (5) Å	µ = 2.09 mm−1
α = 78.811 (2)°	T = 295 K
β = 79.235 (1)°	Block, pale yellow
γ = 79.469 (2)°	0.26 × 0.22 × 0.20 mm
V = 1059.17 (8) Å3

Bruker Kappa APEXII diffractometer	6728 independent reflections
Radiation source: fine-focus sealed tube	3460 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω and φ scans	θmax = 31.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.613, Tmax = 0.680	k = −13→13
27712 measured reflections	l = −18→18

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0879P)2 + 0.2447P] where P = (Fo2 + 2Fc2)/3
6728 reflections	(Δ/σ)max < 0.001
248 parameters	Δρmax = 0.60 e Å−3
1 restraint	Δρmin = −0.63 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.93954 (5)	0.98169 (6)	0.84703 (3)	0.1019 (2)
Cl1	0.49673 (11)	1.20251 (9)	0.60211 (8)	0.0842 (3)
O1	1.0463 (2)	0.8013 (2)	0.67203 (17)	0.0626 (5)
H1	1.0757	0.7517	0.6239	0.094*
O2	1.2797 (2)	0.5219 (2)	0.52053 (15)	0.0637 (5)
N1	1.0370 (2)	0.7096 (2)	0.49638 (17)	0.0473 (5)
N2	1.1026 (2)	0.6271 (2)	0.41810 (17)	0.0465 (5)
H2	1.0646	0.6326	0.3607	0.056*
C1	0.8540 (3)	0.8951 (3)	0.5612 (2)	0.0467 (6)
C2	0.9213 (3)	0.8912 (3)	0.6516 (2)	0.0484 (6)
C3	0.8529 (3)	0.9868 (3)	0.7243 (2)	0.0549 (7)
C4	0.7247 (3)	1.0821 (3)	0.7087 (2)	0.0575 (7)
H4	0.6820	1.1453	0.7575	0.069*
C5	0.6601 (3)	1.0831 (3)	0.6197 (2)	0.0560 (7)
C6	0.7235 (3)	0.9919 (3)	0.5463 (2)	0.0545 (6)
H6	0.6791	0.9948	0.4862	0.065*
C7	0.9190 (3)	0.8017 (3)	0.4805 (2)	0.0504 (6)
H7	0.8762	0.8085	0.4191	0.060*
C8	1.2312 (3)	0.5359 (3)	0.43593 (19)	0.0448 (5)
C9	1.3105 (3)	0.4581 (2)	0.34618 (19)	0.0413 (5)
C10	1.2420 (3)	0.4292 (3)	0.2672 (2)	0.0461 (5)
H10	1.1405	0.4603	0.2676	0.055*
C11	1.3245 (3)	0.3540 (3)	0.1874 (2)	0.0477 (6)
H11	1.2765	0.3344	0.1353	0.057*
C12	1.4758 (3)	0.3071 (2)	0.1826 (2)	0.0444 (5)
C13	1.5416 (3)	0.3359 (3)	0.2627 (2)	0.0538 (6)
H13	1.6432	0.3051	0.2620	0.065*
C14	1.4614 (3)	0.4091 (3)	0.3443 (2)	0.0543 (6)
H14	1.5090	0.4254	0.3980	0.065*
C15	1.5690 (3)	0.2267 (3)	0.0933 (2)	0.0539 (6)
C16	1.4789 (5)	0.2141 (5)	0.0085 (3)	0.0977 (13)
H16A	1.4379	0.3103	−0.0238	0.146*
H16B	1.3995	0.1593	0.0418	0.146*
H16C	1.5423	0.1646	−0.0461	0.146*
C17	1.7001 (5)	0.3051 (4)	0.0402 (3)	0.0918 (13)
H17A	1.6648	0.4066	0.0164	0.138*
H17B	1.7520	0.2610	−0.0208	0.138*
H17C	1.7664	0.2971	0.0912	0.138*
C18	1.6298 (4)	0.0714 (3)	0.1443 (3)	0.0780 (10)
H18A	1.6936	0.0220	0.0898	0.117*
H18B	1.5484	0.0184	0.1756	0.117*
H18C	1.6854	0.0765	0.1995	0.117*
O3	0.8792 (3)	0.6125 (3)	0.29413 (18)	0.0786 (7)
H3	0.8295	0.5667	0.3451	0.118*
C19	0.9211 (6)	0.6211 (10)	0.1011 (4)	0.163 (3)
H19A	0.9967	0.6814	0.0944	0.244*
H19B	0.8696	0.6507	0.0400	0.244*
H19C	0.9665	0.5204	0.1040	0.244*
C20	0.8100 (5)	0.6384 (8)	0.2050 (3)	0.1222 (18)
H20A	0.7549	0.7370	0.1978	0.147*
H20B	0.7393	0.5705	0.2149	0.147*

	U11	U22	U33	U12	U13	U23
Br1	0.0838 (3)	0.1505 (4)	0.0874 (3)	0.0068 (3)	−0.0185 (2)	−0.0770 (3)
Cl1	0.0797 (6)	0.0691 (5)	0.0899 (6)	0.0249 (4)	−0.0068 (5)	−0.0198 (4)
O1	0.0522 (11)	0.0749 (12)	0.0641 (12)	0.0052 (9)	−0.0073 (9)	−0.0354 (10)
O2	0.0541 (11)	0.0963 (15)	0.0461 (10)	−0.0032 (10)	−0.0084 (9)	−0.0323 (10)
N1	0.0503 (12)	0.0485 (11)	0.0446 (11)	−0.0085 (9)	0.0045 (9)	−0.0216 (9)
N2	0.0493 (12)	0.0500 (11)	0.0411 (11)	−0.0020 (9)	0.0002 (9)	−0.0220 (9)
C1	0.0482 (13)	0.0412 (12)	0.0482 (14)	−0.0070 (10)	0.0069 (11)	−0.0151 (10)
C2	0.0495 (14)	0.0473 (13)	0.0482 (14)	−0.0119 (11)	0.0062 (11)	−0.0169 (11)
C3	0.0543 (15)	0.0617 (15)	0.0511 (15)	−0.0137 (12)	0.0077 (12)	−0.0259 (12)
C4	0.0598 (17)	0.0504 (14)	0.0588 (16)	−0.0089 (12)	0.0159 (13)	−0.0242 (12)
C5	0.0571 (16)	0.0425 (13)	0.0598 (17)	0.0001 (11)	0.0065 (13)	−0.0101 (11)
C6	0.0605 (17)	0.0486 (13)	0.0510 (15)	−0.0019 (12)	−0.0039 (12)	−0.0104 (11)
C7	0.0589 (16)	0.0480 (13)	0.0443 (13)	−0.0057 (11)	−0.0001 (11)	−0.0176 (11)
C8	0.0428 (13)	0.0531 (13)	0.0409 (13)	−0.0103 (10)	0.0002 (10)	−0.0170 (10)
C9	0.0417 (12)	0.0429 (11)	0.0392 (12)	−0.0056 (9)	−0.0007 (9)	−0.0129 (9)
C10	0.0396 (12)	0.0534 (13)	0.0459 (13)	0.0008 (10)	−0.0040 (10)	−0.0201 (11)
C11	0.0468 (14)	0.0540 (13)	0.0447 (13)	0.0002 (10)	−0.0079 (11)	−0.0208 (11)
C12	0.0454 (13)	0.0399 (11)	0.0456 (13)	−0.0036 (9)	0.0018 (10)	−0.0129 (10)
C13	0.0358 (12)	0.0667 (16)	0.0591 (16)	0.0023 (11)	−0.0039 (11)	−0.0235 (13)
C14	0.0455 (14)	0.0695 (16)	0.0521 (15)	−0.0036 (12)	−0.0103 (11)	−0.0226 (13)
C15	0.0535 (15)	0.0503 (13)	0.0554 (15)	−0.0023 (11)	0.0069 (12)	−0.0226 (12)
C16	0.093 (3)	0.124 (3)	0.082 (2)	0.017 (2)	−0.009 (2)	−0.068 (2)
C17	0.099 (3)	0.075 (2)	0.091 (3)	−0.0283 (19)	0.048 (2)	−0.0345 (19)
C18	0.077 (2)	0.0517 (16)	0.095 (3)	0.0024 (14)	0.0109 (19)	−0.0212 (16)
O3	0.0644 (14)	0.1174 (19)	0.0548 (12)	−0.0080 (13)	−0.0132 (10)	−0.0176 (12)
C19	0.104 (4)	0.311 (10)	0.079 (3)	−0.029 (5)	−0.018 (3)	−0.046 (5)
C20	0.096 (3)	0.195 (6)	0.079 (3)	−0.014 (3)	−0.029 (3)	−0.027 (3)

Br1—C3	1.880 (3)	C12—C13	1.376 (4)
Cl1—C5	1.733 (3)	C12—C15	1.532 (3)
O1—C2	1.338 (3)	C13—C14	1.385 (4)
O1—H1	0.8200	C13—H13	0.9300
O2—C8	1.221 (3)	C14—H14	0.9300
N1—C7	1.285 (3)	C15—C17	1.516 (4)
N1—N2	1.369 (3)	C15—C16	1.519 (5)
N2—C8	1.362 (3)	C15—C18	1.530 (4)
N2—H2	0.8601	C16—H16A	0.9600
C1—C6	1.392 (4)	C16—H16B	0.9600
C1—C2	1.404 (4)	C16—H16C	0.9600
C1—C7	1.457 (3)	C17—H17A	0.9600
C2—C3	1.402 (3)	C17—H17B	0.9600
C3—C4	1.371 (4)	C17—H17C	0.9600
C4—C5	1.378 (4)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.372 (4)	C18—H18C	0.9600
C6—H6	0.9300	O3—C20	1.369 (5)
C7—H7	0.9300	O3—H3	0.8201
C8—C9	1.485 (3)	C19—C20	1.5362 (10)
C9—C10	1.379 (3)	C19—H19A	0.9600
C9—C14	1.385 (4)	C19—H19B	0.9600
C10—C11	1.384 (3)	C19—H19C	0.9600
C10—H10	0.9300	C20—H20A	0.9700
C11—C12	1.381 (4)	C20—H20B	0.9700
C11—H11	0.9300
C2—O1—H1	109.5	C12—C13—H13	118.9
C7—N1—N2	118.4 (2)	C14—C13—H13	118.9
C8—N2—N1	116.5 (2)	C13—C14—C9	120.0 (2)
C8—N2—H2	121.8	C13—C14—H14	120.0
N1—N2—H2	121.8	C9—C14—H14	120.0
C6—C1—C2	119.7 (2)	C17—C15—C16	109.8 (3)
C6—C1—C7	118.7 (3)	C17—C15—C18	108.2 (3)
C2—C1—C7	121.5 (2)	C16—C15—C18	107.9 (3)
O1—C2—C3	118.6 (3)	C17—C15—C12	109.6 (2)
O1—C2—C1	123.5 (2)	C16—C15—C12	112.6 (2)
C3—C2—C1	117.9 (2)	C18—C15—C12	108.6 (2)
C4—C3—C2	121.9 (3)	C15—C16—H16A	109.5
C4—C3—Br1	119.4 (2)	C15—C16—H16B	109.5
C2—C3—Br1	118.6 (2)	H16A—C16—H16B	109.5
C3—C4—C5	119.1 (2)	C15—C16—H16C	109.5
C3—C4—H4	120.4	H16A—C16—H16C	109.5
C5—C4—H4	120.4	H16B—C16—H16C	109.5
C6—C5—C4	120.9 (3)	C15—C17—H17A	109.5
C6—C5—Cl1	120.5 (3)	C15—C17—H17B	109.5
C4—C5—Cl1	118.6 (2)	H17A—C17—H17B	109.5
C5—C6—C1	120.4 (3)	C15—C17—H17C	109.5
C5—C6—H6	119.8	H17A—C17—H17C	109.5
C1—C6—H6	119.8	H17B—C17—H17C	109.5
N1—C7—C1	118.3 (2)	C15—C18—H18A	109.5
N1—C7—H7	120.8	C15—C18—H18B	109.5
C1—C7—H7	120.8	H18A—C18—H18B	109.5
O2—C8—N2	121.4 (2)	C15—C18—H18C	109.5
O2—C8—C9	122.2 (2)	H18A—C18—H18C	109.5
N2—C8—C9	116.4 (2)	H18B—C18—H18C	109.5
C10—C9—C14	118.8 (2)	C20—O3—H3	109.6
C10—C9—C8	123.9 (2)	C20—C19—H19A	109.5
C14—C9—C8	117.3 (2)	C20—C19—H19B	109.5
C9—C10—C11	119.9 (2)	H19A—C19—H19B	109.5
C9—C10—H10	120.0	C20—C19—H19C	109.5
C11—C10—H10	120.0	H19A—C19—H19C	109.5
C12—C11—C10	122.3 (2)	H19B—C19—H19C	109.5
C12—C11—H11	118.9	O3—C20—C19	112.2 (4)
C10—C11—H11	118.9	O3—C20—H20A	109.2
C13—C12—C11	116.8 (2)	C19—C20—H20A	109.2
C13—C12—C15	120.4 (2)	O3—C20—H20B	109.2
C11—C12—C15	122.8 (2)	C19—C20—H20B	109.2
C12—C13—C14	122.1 (2)	H20A—C20—H20B	107.9
C7—N1—N2—C8	177.0 (2)	N1—N2—C8—C9	−173.9 (2)
C6—C1—C2—O1	179.8 (2)	O2—C8—C9—C10	157.1 (3)
C7—C1—C2—O1	−1.4 (4)	N2—C8—C9—C10	−24.4 (4)
C6—C1—C2—C3	0.0 (4)	O2—C8—C9—C14	−21.3 (4)
C7—C1—C2—C3	178.8 (2)	N2—C8—C9—C14	157.2 (2)
O1—C2—C3—C4	179.9 (2)	C14—C9—C10—C11	−0.7 (4)
C1—C2—C3—C4	−0.3 (4)	C8—C9—C10—C11	−179.0 (2)
O1—C2—C3—Br1	−0.6 (3)	C9—C10—C11—C12	−0.8 (4)
C1—C2—C3—Br1	179.15 (19)	C10—C11—C12—C13	1.3 (4)
C2—C3—C4—C5	0.8 (4)	C10—C11—C12—C15	−178.6 (2)
Br1—C3—C4—C5	−178.6 (2)	C11—C12—C13—C14	−0.4 (4)
C3—C4—C5—C6	−1.0 (4)	C15—C12—C13—C14	179.5 (3)
C3—C4—C5—Cl1	179.1 (2)	C12—C13—C14—C9	−1.1 (4)
C4—C5—C6—C1	0.8 (4)	C10—C9—C14—C13	1.6 (4)
Cl1—C5—C6—C1	−179.4 (2)	C8—C9—C14—C13	−180.0 (3)
C2—C1—C6—C5	−0.3 (4)	C13—C12—C15—C17	−53.7 (4)
C7—C1—C6—C5	−179.1 (2)	C11—C12—C15—C17	126.2 (3)
N2—N1—C7—C1	−176.7 (2)	C13—C12—C15—C16	−176.2 (3)
C6—C1—C7—N1	−178.0 (2)	C11—C12—C15—C16	3.7 (4)
C2—C1—C7—N1	3.2 (4)	C13—C12—C15—C18	64.3 (3)
N1—N2—C8—O2	4.6 (4)	C11—C12—C15—C18	−115.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.577 (3)	145
N2—H2···O3	0.86	2.10	2.865 (3)	147
O3—H3···O2i	0.82	1.94	2.755 (3)	171
C14—H14···O2ii	0.93	2.54	3.418 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.577 (3)	145
N2—H2⋯O3	0.86	2.10	2.865 (3)	147
O3—H3⋯O2i	0.82	1.94	2.755 (3)	171
C14—H14⋯O2ii	0.93	2.54	3.418 (3)	157

Symmetry codes: (i) ; (ii) .