N′-[(1E)-3-Bromo-5-chloro-2-hy­droxy­benzyl­idene]-4-tert-butyl­benzo­hydrazide ethanol monosolvate

Thirugnanasundar, A.; Parthipan, K.; Anthonisamy, V.S.X.; Chakkaravarthi, G.; Rajagopal, G.

doi:10.1107/S160053681104027X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2857

doi:10.1107/S160053681104027X

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N′-[(1E)-3-Bromo-5-chloro-2-hydroxybenzylidene]-4-tert-butylbenzohydrazide ethanol monosolvate

A. Thirugnanasundar,^a K. Parthipan,^b V. S. Xavier Anthonisamy,^c G. Chakkaravarthi ^d ^* and G. Rajagopal ^c ^*

^aDepartment of Chemistry, Velalar College of Engineering and Technology, Erode 638 009, India, ^bDepartment of Chemistry, Pondicherry University, Pondicherry 605014, India, ^cDepartment of Chemistry, Government Arts College, Melur 625 106, India, and ^dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

(Received 20 September 2011; accepted 29 September 2011; online 5 October 2011)

In the title compound, C₁₈H₁₈BrClN₂O₂·C₂H₆O, the hydroxy group forms an intramolecular O—H⋯N hydrogen bond, which influences the conformation of the Shiff base molecule, where the two aromatic rings form a dihedral angle of 21.67 (8)°. Intermolecular N—H⋯O and O—H⋯O hydrogen bonds link two Shiff base molecules and two solvent molecules into a centrosymmetric heterotetramer. Weak intermolecular C—H⋯O interactions link further tetramers 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_r = 455.77
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.180
S = 1.03
6728 reflections
248 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.63 e Å⁻³

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) -x+2, -y+1, -z+1; (ii) -x+3, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681104027X/cv5157sup1.cif

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

Supporting information file. DOI: 10.1107/S160053681104027X/cv5157Isup3.cml

checkCIF report

Comment top

Schiff base compounds have been widely used as versatile ligands in coordination chemistry (Shivakumar et al., 2008; Prabhakaran et al., 2006). Schiff bases are also known to exhibit anticancer, antibacterial and antifungal activities (Dao et al., 2000; Karthikeyan et al., 2006). Herewith we present the title compound (I), which is a new Schiff base.

In (I) (Fig. 1), the geometric parameters are comparable with the those reported for similar structures ( Fun et al., 2008; Thirugnanasundar et al., 2011). The dihedral angle between the two aromatic rings is 21.67 (8)°. Intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) link two Shiff base molecules and two solvent molecules into centrosymmetric tetramer (Fig. 2). Weak intermolecular C—H···O interactions (Table 1) link further the tetramers related by translation along axis a into chains.

Related literature top

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 top

4-tert-Butylbenzoichydrazide (5 mmol) was dissolved in 20 mL of dry ethanol with stirring and warming over a period of 10 min. To the warm hydrazide solution, 3-bromo-5-chloro salicylaldehyde (5 mmol) in 20 mL of dry ethanol was added and the mixture was stirred and slowly refluxed for 2 h. The mixture was then cooled down to room temperature when pale yellow crystalline compound precipitated. The compound was collected by filtration, washed with cold ethanol and dried in vacuum. Single crystals suitable for the X-ray diffraction were obtained by slow evaporation of a solution of the title compound in ethanol at room temperature. Melting Point: 498 - 500 K.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. Dashed lines denote hydrogen bonds.
	Fig. 2. Hydrogen-bonded (dashed lines) tetramer in (I), viewed down a axis. H atoms not involved in hydrogen bonding have been omitted.

N'-[(1E)-3-Bromo-5-chloro-2-hydroxybenzylidene]-4- tert-butylbenzohydrazide ethanol monosolvate top

Crystal data top

C₁₈H₁₈BrClN₂O₂·C₂H₆O	Z = 2
M_r = 455.77	F(000) = 468
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0879P)² + 0.2447P] where P = (F_o² + 2F_c²)/3
6728 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.60 e Å⁻³
1 restraint	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₁₈H₁₈BrClN₂O₂·C₂H₆O	γ = 79.469 (2)°
M_r = 455.77	V = 1059.17 (8) Å³
Triclinic, P1	Z = 2
a = 9.2478 (4) Å	Mo Kα radiation
b = 9.4057 (4) Å	µ = 2.09 mm⁻¹
c = 12.7838 (5) Å	T = 295 K
α = 78.811 (2)°	0.26 × 0.22 × 0.20 mm
β = 79.235 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	6728 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3460 reflections with I > 2σ(I)
T_min = 0.613, T_max = 0.680	R_int = 0.033
27712 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	1 restraint
wR(F²) = 0.180	H-atom parameters constrained
S = 1.03	Δρ_max = 0.60 e Å⁻³
6728 reflections	Δρ_min = −0.63 e Å⁻³
248 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1; (ii) −x+3, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈BrClN₂O₂·C₂H₆O
M_r	455.77
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.2478 (4), 9.4057 (4), 12.7838 (5)
α, β, γ (°)	78.811 (2), 79.235 (1), 79.469 (2)
V (Å³)	1059.17 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.09
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.613, 0.680
No. of measured, independent and observed [I > 2σ(I)] reflections	27712, 6728, 3460
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.726

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.180, 1.03
No. of reflections	6728
No. of parameters	248
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.63

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1; (ii) −x+3, −y+1, −z+1.

Acknowledgements

The authors acknowledge SAIF, IIT, Madras, for the X-ray data collection.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805–813. Web of Science CrossRef PubMed CAS Google Scholar
Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595. Web of Science CSD CrossRef IUCr Journals Google Scholar
Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482–7489. Web of Science CrossRef PubMed CAS Google Scholar
Prabhakaran, R., Huang, R. & Natarajan, K. (2006). Inorg. Chim. Acta, 359, 3359–3362. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shivakumar, K., Shashidhar, T., Reddy, P. V. & Halli, M. B. (2008). J. Coord. Chem. 61, 2274–2287. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thirugnanasundar, A., Suresh, J., Ramu, A. & RajaGopal, G. (2011). Acta Cryst. E67, o2303. Web of Science CSD CrossRef IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-[(1E)-3-Bromo-5-chloro-2-hy­dr­oxy­benzyl­­idene]-4-tert-butyl­benzo­hydrazide ethanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-[(1E)-3-Bromo-5-chloro-2-hydroxybenzylidene]-4-tert-butylbenzohydrazide ethanol monosolvate