2-Hydr-oxy-(2-methyl-1H-indol-3-ylmethyl-idene)benzohydrazide ethanol solvate.

In the title compound, C(17)H(15)N(3)O(2)·C(2)H(6)O, Schiff base molecules are linked by a hydr-oxy-amido hydrogen bond into a helical chain running along the b axis. This chain is consolidated by two other hydrogen bonds; the ethanol solvent mol-ecule is a hydrogen-bond donor to the amide group and a hydrogen-bond acceptor for the indolyl NH group of an adjacent Schiff base mol-ecule.

Related literature

For reports on the medicinal properties of the unsubstituted compound, indol-3-ylmethyl­idene-2-hydroxy­benzohydrazide, see: Alemany et al. (1967 ▶); Fujikawa et al. (1966 ▶); Nakata et al. (1966 ▶); Singh et al. (1984 ▶).

Experimental

Crystal data

C17H15N3O2·C2H6O

M = 339.39

Monoclinic,

a = 7.5907 (1) Å

b = 11.2269 (2) Å

c = 20.3014 (3) Å

β = 91.924 (1)°

V = 1729.11 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 (2) K

0.34 × 0.27 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

20827 measured reflections

3967 independent reflections

2869 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.162

S = 1.13

3967 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011756/sg2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011756/sg2238Isup2.hkl

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

C17H15N3O2·C2H6O	F000 = 720
Mr = 339.39	Dx = 1.304 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6771 reflections
a = 7.5907 (1) Å	θ = 2.7–28.2º
b = 11.2269 (2) Å	µ = 0.09 mm−1
c = 20.3014 (3) Å	T = 100 (2) K
β = 91.924 (1)º	Prism, yellow
V = 1729.11 (5) Å3	0.34 × 0.27 × 0.12 mm
Z = 4

Bruker SMART APEX diffractometer	2869 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
Monochromator: graphite	θmax = 27.5º
T = 100(2) K	θmin = 2.0º
ω scans	h = −9→9
Absorption correction: None	k = −14→14
20827 measured reflections	l = −26→22
3967 independent reflections

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.0721P)2 + 0.9553P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max = 0.001
3967 reflections	Δρmax = 0.31 e Å−3
230 parameters	Δρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
O1	0.60372 (18)	0.39960 (12)	0.26124 (6)	0.0287 (3)
H1O	0.6488	0.3342	0.2507	0.043*
O2	0.26721 (17)	0.69310 (12)	0.26809 (7)	0.0272 (3)
O3	−0.0963 (2)	0.65666 (15)	0.29094 (8)	0.0409 (4)
H3O	0.0126	0.6698	0.2916	0.061*
N1	0.3897 (2)	0.53879 (15)	0.32419 (7)	0.0255 (4)
H1N	0.4563	0.4746	0.3236	0.031*
N2	0.3081 (2)	0.57121 (15)	0.38183 (8)	0.0263 (4)
N3	0.1852 (2)	0.47451 (15)	0.59623 (8)	0.0265 (4)
H3N	0.1730	0.4372	0.6339	0.032*
C1	0.5678 (2)	0.46480 (17)	0.20605 (9)	0.0243 (4)
C2	0.6339 (3)	0.43017 (18)	0.14536 (10)	0.0283 (4)
H2	0.7025	0.3597	0.1425	0.034*
C3	0.5997 (3)	0.4978 (2)	0.08976 (10)	0.0313 (5)
H3	0.6462	0.4742	0.0489	0.038*
C4	0.4981 (3)	0.60009 (19)	0.09301 (10)	0.0311 (4)
H4	0.4760	0.6471	0.0547	0.037*
C5	0.4291 (2)	0.63320 (18)	0.15254 (9)	0.0270 (4)
H5	0.3583	0.7028	0.1545	0.032*
C6	0.4616 (2)	0.56639 (17)	0.20990 (9)	0.0233 (4)
C7	0.3674 (2)	0.60467 (17)	0.26980 (9)	0.0233 (4)
C8	0.3263 (2)	0.49282 (18)	0.42813 (9)	0.0258 (4)
H8	0.3859	0.4204	0.4194	0.031*
C9	0.2589 (2)	0.51224 (18)	0.49235 (9)	0.0258 (4)
C10	0.2617 (2)	0.42767 (18)	0.54211 (9)	0.0266 (4)
C11	0.3331 (3)	0.30424 (19)	0.54307 (10)	0.0324 (5)
H11A	0.2672	0.2556	0.5739	0.049*
H11B	0.4578	0.3060	0.5572	0.049*
H11C	0.3212	0.2698	0.4988	0.049*
C12	0.1752 (2)	0.61732 (18)	0.51780 (9)	0.0262 (4)
C13	0.1327 (3)	0.73007 (19)	0.49295 (10)	0.0304 (4)
H13	0.1621	0.7517	0.4494	0.036*
C14	0.0472 (3)	0.8094 (2)	0.53269 (11)	0.0343 (5)
H14	0.0185	0.8864	0.5161	0.041*
C15	0.0014 (3)	0.7792 (2)	0.59706 (11)	0.0359 (5)
H15	−0.0586	0.8356	0.6231	0.043*
C16	0.0425 (3)	0.66914 (19)	0.62286 (10)	0.0314 (5)
H16	0.0123	0.6483	0.6664	0.038*
C17	0.1302 (2)	0.58892 (18)	0.58288 (9)	0.0262 (4)
C18	−0.1888 (3)	0.7654 (2)	0.28171 (11)	0.0384 (5)
H18A	−0.3059	0.7584	0.3014	0.046*
H18B	−0.2077	0.7799	0.2339	0.046*
C19	−0.0926 (3)	0.8698 (2)	0.31203 (13)	0.0453 (6)
H19A	−0.1676	0.9407	0.3088	0.068*
H19B	0.0163	0.8839	0.2886	0.068*
H19C	−0.0637	0.8529	0.3585	0.068*

	U11	U22	U33	U12	U13	U23
O1	0.0333 (8)	0.0315 (7)	0.0215 (7)	0.0069 (6)	0.0051 (5)	0.0015 (6)
O2	0.0237 (7)	0.0306 (7)	0.0276 (7)	0.0012 (5)	0.0066 (5)	0.0015 (6)
O3	0.0288 (8)	0.0494 (10)	0.0452 (10)	−0.0007 (7)	0.0132 (7)	0.0105 (7)
N1	0.0239 (8)	0.0333 (9)	0.0198 (8)	0.0029 (7)	0.0060 (6)	−0.0004 (7)
N2	0.0214 (8)	0.0376 (9)	0.0202 (8)	−0.0009 (7)	0.0053 (6)	−0.0021 (7)
N3	0.0232 (8)	0.0368 (9)	0.0197 (8)	−0.0011 (7)	0.0043 (6)	0.0004 (7)
C1	0.0210 (9)	0.0310 (10)	0.0209 (9)	−0.0029 (7)	0.0021 (7)	0.0010 (7)
C2	0.0244 (9)	0.0346 (10)	0.0260 (10)	0.0019 (8)	0.0041 (7)	−0.0026 (8)
C3	0.0292 (10)	0.0440 (12)	0.0211 (10)	−0.0011 (9)	0.0062 (8)	−0.0014 (8)
C4	0.0327 (10)	0.0399 (11)	0.0208 (9)	−0.0021 (9)	0.0019 (8)	0.0045 (8)
C5	0.0251 (9)	0.0308 (10)	0.0252 (10)	−0.0008 (8)	0.0021 (7)	0.0016 (8)
C6	0.0194 (8)	0.0302 (10)	0.0205 (9)	−0.0040 (7)	0.0028 (7)	−0.0016 (7)
C7	0.0185 (8)	0.0279 (9)	0.0236 (9)	−0.0039 (7)	0.0016 (7)	−0.0004 (7)
C8	0.0192 (9)	0.0341 (10)	0.0242 (10)	−0.0012 (7)	0.0029 (7)	−0.0017 (8)
C9	0.0173 (8)	0.0379 (11)	0.0224 (9)	−0.0022 (7)	0.0018 (7)	−0.0010 (8)
C10	0.0184 (8)	0.0391 (11)	0.0224 (9)	−0.0029 (8)	0.0034 (7)	−0.0018 (8)
C11	0.0308 (10)	0.0400 (11)	0.0268 (10)	−0.0006 (9)	0.0069 (8)	0.0005 (9)
C12	0.0167 (8)	0.0396 (11)	0.0225 (9)	−0.0030 (8)	0.0022 (7)	−0.0026 (8)
C13	0.0222 (9)	0.0410 (11)	0.0279 (10)	−0.0020 (8)	0.0021 (7)	0.0017 (9)
C14	0.0264 (10)	0.0362 (11)	0.0402 (12)	0.0025 (9)	−0.0012 (9)	0.0009 (9)
C15	0.0280 (10)	0.0450 (12)	0.0349 (11)	0.0038 (9)	0.0026 (8)	−0.0087 (10)
C16	0.0238 (9)	0.0447 (12)	0.0258 (10)	−0.0009 (8)	0.0042 (8)	−0.0055 (9)
C17	0.0177 (8)	0.0382 (11)	0.0226 (9)	−0.0032 (7)	0.0012 (7)	−0.0020 (8)
C18	0.0253 (10)	0.0568 (14)	0.0332 (11)	0.0033 (10)	0.0047 (8)	0.0130 (10)
C19	0.0292 (11)	0.0548 (15)	0.0520 (15)	0.0108 (10)	0.0026 (10)	0.0041 (12)

O1—C1	1.358 (2)	C8—H8	0.9500
O1—H1O	0.8400	C9—C10	1.386 (3)
O2—C7	1.250 (2)	C9—C12	1.444 (3)
O3—C18	1.417 (3)	C10—C11	1.488 (3)
O3—H3O	0.8400	C11—H11A	0.9800
N1—C7	1.335 (2)	C11—H11B	0.9800
N1—N2	1.391 (2)	C11—H11C	0.9800
N1—H1N	0.8800	C12—C13	1.396 (3)
N2—C8	1.292 (3)	C12—C17	1.412 (3)
N3—C10	1.365 (2)	C13—C14	1.379 (3)
N3—C17	1.375 (3)	C13—H13	0.9500
N3—H3N	0.8800	C14—C15	1.405 (3)
C1—C6	1.401 (3)	C14—H14	0.9500
C1—C2	1.401 (3)	C15—C16	1.374 (3)
C2—C3	1.378 (3)	C15—H15	0.9500
C2—H2	0.9500	C16—C17	1.396 (3)
C3—C4	1.386 (3)	C16—H16	0.9500
C3—H3	0.9500	C18—C19	1.502 (4)
C4—C5	1.384 (3)	C18—H18A	0.9900
C4—H4	0.9500	C18—H18B	0.9900
C5—C6	1.400 (3)	C19—H19A	0.9800
C5—H5	0.9500	C19—H19B	0.9800
C6—C7	1.494 (3)	C19—H19C	0.9800
C8—C9	1.433 (3)
C1—O1—H1O	109.5	C9—C10—C11	130.10 (18)
C18—O3—H3O	109.5	C10—C11—H11A	109.5
C7—N1—N2	120.20 (16)	C10—C11—H11B	109.5
C7—N1—H1N	119.9	H11A—C11—H11B	109.5
N2—N1—H1N	119.9	C10—C11—H11C	109.5
C8—N2—N1	113.21 (16)	H11A—C11—H11C	109.5
C10—N3—C17	109.62 (16)	H11B—C11—H11C	109.5
C10—N3—H3N	125.2	C13—C12—C17	118.84 (18)
C17—N3—H3N	125.2	C13—C12—C9	135.28 (18)
O1—C1—C6	119.52 (16)	C17—C12—C9	105.88 (17)
O1—C1—C2	120.54 (17)	C14—C13—C12	118.82 (19)
C6—C1—C2	119.93 (17)	C14—C13—H13	120.6
C3—C2—C1	120.29 (19)	C12—C13—H13	120.6
C3—C2—H2	119.9	C13—C14—C15	121.6 (2)
C1—C2—H2	119.9	C13—C14—H14	119.2
C2—C3—C4	120.49 (19)	C15—C14—H14	119.2
C2—C3—H3	119.8	C16—C15—C14	120.8 (2)
C4—C3—H3	119.8	C16—C15—H15	119.6
C5—C4—C3	119.45 (19)	C14—C15—H15	119.6
C5—C4—H4	120.3	C15—C16—C17	117.72 (19)
C3—C4—H4	120.3	C15—C16—H16	121.1
C4—C5—C6	121.42 (19)	C17—C16—H16	121.1
C4—C5—H5	119.3	N3—C17—C16	129.46 (18)
C6—C5—H5	119.3	N3—C17—C12	108.30 (17)
C5—C6—C1	118.38 (17)	C16—C17—C12	122.23 (19)
C5—C6—C7	116.57 (17)	O3—C18—C19	112.73 (18)
C1—C6—C7	124.88 (17)	O3—C18—H18A	109.0
O2—C7—N1	121.54 (17)	C19—C18—H18A	109.0
O2—C7—C6	120.86 (17)	O3—C18—H18B	109.0
N1—C7—C6	117.57 (16)	C19—C18—H18B	109.0
N2—C8—C9	121.71 (18)	H18A—C18—H18B	107.8
N2—C8—H8	119.1	C18—C19—H19A	109.5
C9—C8—H8	119.1	C18—C19—H19B	109.5
C10—C9—C8	124.18 (18)	H19A—C19—H19B	109.5
C10—C9—C12	107.16 (17)	C18—C19—H19C	109.5
C8—C9—C12	128.66 (18)	H19A—C19—H19C	109.5
N3—C10—C9	109.04 (18)	H19B—C19—H19C	109.5
N3—C10—C11	120.86 (17)
C7—N1—N2—C8	173.12 (16)	C17—N3—C10—C11	−179.95 (17)
O1—C1—C2—C3	−178.81 (17)	C8—C9—C10—N3	−179.13 (17)
C6—C1—C2—C3	2.2 (3)	C12—C9—C10—N3	−0.1 (2)
C1—C2—C3—C4	−0.7 (3)	C8—C9—C10—C11	1.4 (3)
C2—C3—C4—C5	−0.8 (3)	C12—C9—C10—C11	−179.53 (19)
C3—C4—C5—C6	0.8 (3)	C10—C9—C12—C13	−179.7 (2)
C4—C5—C6—C1	0.6 (3)	C8—C9—C12—C13	−0.7 (4)
C4—C5—C6—C7	−174.79 (17)	C10—C9—C12—C17	−0.4 (2)
O1—C1—C6—C5	178.89 (16)	C8—C9—C12—C17	178.61 (18)
C2—C1—C6—C5	−2.1 (3)	C17—C12—C13—C14	−0.4 (3)
O1—C1—C6—C7	−6.1 (3)	C9—C12—C13—C14	178.8 (2)
C2—C1—C6—C7	172.88 (17)	C12—C13—C14—C15	−0.3 (3)
N2—N1—C7—O2	−3.4 (3)	C13—C14—C15—C16	0.7 (3)
N2—N1—C7—C6	178.81 (15)	C14—C15—C16—C17	−0.2 (3)
C5—C6—C7—O2	−1.0 (3)	C10—N3—C17—C16	178.45 (19)
C1—C6—C7—O2	−176.05 (17)	C10—N3—C17—C12	−0.8 (2)
C5—C6—C7—N1	176.83 (16)	C15—C16—C17—N3	−179.69 (19)
C1—C6—C7—N1	1.8 (3)	C15—C16—C17—C12	−0.5 (3)
N1—N2—C8—C9	176.97 (16)	C13—C12—C17—N3	−179.82 (16)
N2—C8—C9—C10	174.44 (18)	C9—C12—C17—N3	0.7 (2)
N2—C8—C9—C12	−4.4 (3)	C13—C12—C17—C16	0.9 (3)
C17—N3—C10—C9	0.5 (2)	C9—C12—C17—C16	−178.58 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2i	0.84	1.76	2.594 (2)	176
O3—H3o···O2	0.84	2.02	2.843 (2)	165
N1—H1n···O1	0.88	1.91	2.618 (2)	136
N3—H3n···O3ii	0.88	1.96	2.824 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2i	0.84	1.76	2.594 (2)	176
O3—H3o⋯O2	0.84	2.02	2.843 (2)	165
N1—H1n⋯O1	0.88	1.91	2.618 (2)	136
N3—H3n⋯O3ii	0.88	1.96	2.824 (2)	168

Symmetry codes: (i) ; (ii) .