N-Acetyl-2-hydroxy-N'-[methoxy(1-methylindol-2-yl)methyl]benzohydrazide.

In the crystal structure of the title Schiff-base, C(20)H(21)N(3)O(4), the amino group forms an N-H⋯O hydrogen bond to the acetyl group of an adjacent mol-ecule, forming a zigzag chain. The 2-hydr-oxy group is inter-nally hydrogen bonded to the amido group though an O-H⋯O hydrogen bond.

Related literature

For medicinal uses of the precursor Schiff base, see: Jin et al. (2006 ▶); Joshi et al. (2008 ▶); Szczepankiewicz et al. (2001 ▶).

Experimental

Crystal data

C20H21N3O4

M = 367.40

Monoclinic,

a = 11.0075 (3) Å

b = 10.5197 (3) Å

c = 15.4479 (4) Å

β = 93.967 (2)°

V = 1784.51 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 (2) K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

16316 measured reflections

4072 independent reflections

2646 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.120

S = 1.02

4072 reflections

255 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.26 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/S1600536808026846/tk2298sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026846/tk2298Isup2.hkl

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

C20H21N3O4	F000 = 776
Mr = 367.40	Dx = 1.367 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1739 reflections
a = 11.0075 (3) Å	θ = 2.2–21.4º
b = 10.5197 (3) Å	µ = 0.10 mm−1
c = 15.4479 (4) Å	T = 100 (2) K
β = 93.967 (2)º	Block, colorless
V = 1784.51 (8) Å3	0.20 × 0.15 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	2646 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.065
Monochromator: graphite	θmax = 27.5º
T = 100(2) K	θmin = 2.2º
ω scans	h = −14→14
Absorption correction: None	k = −13→13
16316 measured reflections	l = −20→20
4072 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 atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.3679P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4072 reflections	Δρmax = 0.26 e Å−3
255 parameters	Δρmin = −0.26 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
O1	0.75833 (13)	0.62701 (15)	0.28349 (10)	0.0328 (4)
H1O	0.717 (2)	0.5560 (16)	0.2811 (18)	0.069 (10)*
O2	0.57533 (11)	0.47150 (13)	0.28757 (9)	0.0266 (3)
O3	0.27682 (12)	0.25872 (13)	0.22300 (9)	0.0279 (3)
O4	0.41144 (11)	0.35118 (13)	0.43051 (8)	0.0257 (3)
N1	0.38731 (14)	0.55433 (15)	0.29735 (10)	0.0197 (4)
H1N	0.3430 (17)	0.6189 (15)	0.3061 (14)	0.037 (6)*
N2	0.33109 (13)	0.43653 (14)	0.29605 (10)	0.0188 (3)
N3	0.12618 (13)	0.52539 (15)	0.40494 (10)	0.0205 (4)
C1	0.68446 (17)	0.7144 (2)	0.31706 (12)	0.0262 (5)
C2	0.73287 (19)	0.8337 (2)	0.33795 (14)	0.0315 (5)
H2	0.8144	0.8530	0.3262	0.038*
C3	0.6634 (2)	0.9230 (2)	0.37533 (14)	0.0354 (5)
H3	0.6972	1.0042	0.3892	0.042*
C4	0.54370 (19)	0.8971 (2)	0.39356 (13)	0.0308 (5)
H4	0.4966	0.9592	0.4209	0.037*
C5	0.49478 (18)	0.78036 (18)	0.37132 (12)	0.0249 (4)
H5	0.4132	0.7621	0.3837	0.030*
C6	0.56213 (17)	0.68846 (18)	0.33118 (12)	0.0225 (4)
C7	0.51091 (17)	0.56257 (18)	0.30497 (11)	0.0207 (4)
C8	0.31298 (16)	0.36884 (19)	0.22067 (12)	0.0221 (4)
C9	0.33655 (19)	0.4356 (2)	0.13833 (13)	0.0294 (5)
H9A	0.3008	0.3867	0.0889	0.044*
H9B	0.4246	0.4435	0.1337	0.044*
H9C	0.2997	0.5204	0.1383	0.044*
C10	0.30451 (16)	0.38509 (18)	0.38166 (12)	0.0212 (4)
H10	0.2504	0.3091	0.3736	0.025*
C11	0.24263 (16)	0.48432 (18)	0.43178 (12)	0.0208 (4)
C12	0.28551 (17)	0.55066 (18)	0.50327 (12)	0.0227 (4)
H12	0.3624	0.5400	0.5343	0.027*
C13	0.19310 (17)	0.63891 (18)	0.52267 (12)	0.0222 (4)
C14	0.18300 (18)	0.73351 (19)	0.58605 (12)	0.0261 (5)
H14	0.2474	0.7477	0.6291	0.031*
C15	0.07752 (18)	0.8057 (2)	0.58468 (13)	0.0282 (5)
H15	0.0704	0.8708	0.6267	0.034*
C16	−0.01854 (18)	0.7841 (2)	0.52232 (13)	0.0295 (5)
H16	−0.0899	0.8348	0.5230	0.035*
C17	−0.01235 (17)	0.6909 (2)	0.45972 (13)	0.0260 (5)
H17	−0.0785	0.6754	0.4182	0.031*
C18	0.09490 (16)	0.62076 (18)	0.46006 (12)	0.0220 (4)
C19	0.05096 (17)	0.4838 (2)	0.32897 (12)	0.0269 (5)
H19A	−0.0351	0.4872	0.3415	0.040*
H19B	0.0726	0.3963	0.3144	0.040*
H19C	0.0647	0.5397	0.2799	0.040*
C20	0.4677 (2)	0.24041 (19)	0.39780 (14)	0.0313 (5)
H20A	0.5395	0.2183	0.4358	0.047*
H20B	0.4924	0.2574	0.3392	0.047*
H20C	0.4097	0.1696	0.3960	0.047*

	U11	U22	U33	U12	U13	U23
O1	0.0245 (7)	0.0335 (9)	0.0408 (9)	−0.0008 (7)	0.0048 (6)	0.0009 (7)
O2	0.0224 (7)	0.0240 (8)	0.0339 (8)	0.0036 (6)	0.0054 (6)	−0.0027 (6)
O3	0.0311 (8)	0.0184 (8)	0.0342 (8)	−0.0058 (6)	0.0016 (6)	−0.0067 (6)
O4	0.0282 (7)	0.0211 (8)	0.0272 (7)	0.0051 (6)	−0.0028 (6)	−0.0001 (6)
N1	0.0201 (8)	0.0107 (8)	0.0284 (9)	−0.0007 (7)	0.0024 (7)	−0.0012 (7)
N2	0.0219 (8)	0.0112 (8)	0.0235 (8)	−0.0031 (6)	0.0023 (6)	−0.0011 (7)
N3	0.0213 (8)	0.0190 (9)	0.0213 (8)	−0.0025 (7)	0.0010 (6)	−0.0028 (7)
C1	0.0270 (10)	0.0277 (12)	0.0236 (10)	−0.0010 (9)	−0.0011 (8)	0.0057 (9)
C2	0.0291 (11)	0.0302 (12)	0.0345 (12)	−0.0109 (10)	−0.0027 (9)	0.0081 (10)
C3	0.0452 (13)	0.0230 (12)	0.0364 (12)	−0.0101 (10)	−0.0088 (10)	0.0048 (10)
C4	0.0420 (13)	0.0197 (11)	0.0297 (11)	−0.0021 (9)	−0.0028 (10)	−0.0017 (9)
C5	0.0296 (10)	0.0209 (11)	0.0239 (10)	−0.0027 (9)	−0.0014 (8)	0.0013 (9)
C6	0.0252 (10)	0.0184 (10)	0.0236 (10)	−0.0025 (8)	0.0000 (8)	0.0049 (8)
C7	0.0243 (10)	0.0205 (10)	0.0172 (9)	−0.0013 (8)	0.0020 (7)	0.0030 (8)
C8	0.0194 (9)	0.0207 (11)	0.0259 (10)	0.0033 (8)	0.0002 (8)	−0.0026 (8)
C9	0.0338 (11)	0.0306 (12)	0.0241 (10)	−0.0007 (10)	0.0028 (9)	−0.0032 (9)
C10	0.0228 (9)	0.0176 (10)	0.0232 (10)	−0.0010 (8)	0.0007 (8)	0.0005 (8)
C11	0.0222 (9)	0.0175 (10)	0.0228 (9)	−0.0016 (8)	0.0022 (8)	0.0017 (8)
C12	0.0238 (10)	0.0231 (11)	0.0213 (9)	0.0003 (8)	0.0008 (8)	0.0007 (8)
C13	0.0251 (10)	0.0199 (10)	0.0218 (10)	−0.0024 (8)	0.0036 (8)	0.0030 (8)
C14	0.0304 (11)	0.0268 (12)	0.0216 (10)	−0.0033 (9)	0.0043 (8)	−0.0024 (9)
C15	0.0356 (11)	0.0238 (11)	0.0263 (10)	0.0006 (9)	0.0090 (9)	−0.0047 (9)
C16	0.0282 (11)	0.0289 (12)	0.0326 (11)	0.0042 (9)	0.0101 (9)	0.0009 (10)
C17	0.0229 (10)	0.0266 (11)	0.0286 (11)	−0.0011 (8)	0.0036 (8)	0.0012 (9)
C18	0.0236 (9)	0.0193 (10)	0.0236 (10)	−0.0040 (8)	0.0059 (8)	0.0000 (8)
C19	0.0247 (10)	0.0279 (12)	0.0274 (11)	−0.0023 (9)	−0.0028 (8)	−0.0050 (9)
C20	0.0367 (12)	0.0185 (11)	0.0378 (12)	0.0085 (9)	−0.0026 (10)	0.0007 (9)

O1—C1	1.354 (2)	C8—C9	1.491 (3)
O1—H1O	0.871 (10)	C9—H9A	0.9800
O2—C7	1.233 (2)	C9—H9B	0.9800
O3—C8	1.226 (2)	C9—H9C	0.9800
O4—C10	1.400 (2)	C10—C11	1.492 (3)
O4—C20	1.428 (2)	C10—H10	1.0000
N1—C7	1.360 (2)	C11—C12	1.363 (3)
N1—N2	1.385 (2)	C12—C13	1.424 (3)
N1—H1N	0.852 (9)	C12—H12	0.9500
N2—C8	1.368 (2)	C13—C14	1.406 (3)
N2—C10	1.477 (2)	C13—C18	1.413 (3)
N3—C18	1.375 (2)	C14—C15	1.387 (3)
N3—C11	1.389 (2)	C14—H14	0.9500
N3—C19	1.456 (2)	C15—C16	1.399 (3)
C1—C2	1.393 (3)	C15—H15	0.9500
C1—C6	1.406 (3)	C16—C17	1.382 (3)
C2—C3	1.365 (3)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.392 (3)
C3—C4	1.393 (3)	C17—H17	0.9500
C3—H3	0.9500	C19—H19A	0.9800
C4—C5	1.375 (3)	C19—H19B	0.9800
C4—H4	0.9500	C19—H19C	0.9800
C5—C6	1.390 (3)	C20—H20A	0.9800
C5—H5	0.9500	C20—H20B	0.9800
C6—C7	1.485 (3)	C20—H20C	0.9800
C1—O1—H1O	106.0 (19)	O4—C10—C11	107.19 (14)
C10—O4—C20	112.71 (14)	N2—C10—C11	109.52 (15)
C7—N1—N2	120.11 (16)	O4—C10—H10	109.6
C7—N1—H1N	121.0 (15)	N2—C10—H10	109.6
N2—N1—H1N	117.1 (15)	C11—C10—H10	109.6
C8—N2—N1	121.13 (15)	C12—C11—N3	110.09 (17)
C8—N2—C10	123.05 (15)	C12—C11—C10	129.33 (17)
N1—N2—C10	115.52 (14)	N3—C11—C10	120.52 (16)
C18—N3—C11	107.92 (15)	C11—C12—C13	106.97 (16)
C18—N3—C19	124.45 (16)	C11—C12—H12	126.5
C11—N3—C19	127.50 (16)	C13—C12—H12	126.5
O1—C1—C2	118.06 (18)	C14—C13—C18	118.61 (18)
O1—C1—C6	122.32 (18)	C14—C13—C12	134.43 (18)
C2—C1—C6	119.6 (2)	C18—C13—C12	106.95 (17)
C3—C2—C1	120.1 (2)	C15—C14—C13	118.93 (18)
C3—C2—H2	119.9	C15—C14—H14	120.5
C1—C2—H2	119.9	C13—C14—H14	120.5
C2—C3—C4	121.1 (2)	C14—C15—C16	120.91 (19)
C2—C3—H3	119.4	C14—C15—H15	119.5
C4—C3—H3	119.4	C16—C15—H15	119.5
C5—C4—C3	118.9 (2)	C17—C16—C15	121.71 (19)
C5—C4—H4	120.5	C17—C16—H16	119.1
C3—C4—H4	120.5	C15—C16—H16	119.1
C4—C5—C6	121.40 (19)	C16—C17—C18	117.16 (18)
C4—C5—H5	119.3	C16—C17—H17	121.4
C6—C5—H5	119.3	C18—C17—H17	121.4
C5—C6—C1	118.71 (18)	N3—C18—C17	129.29 (17)
C5—C6—C7	122.54 (17)	N3—C18—C13	108.07 (16)
C1—C6—C7	118.73 (18)	C17—C18—C13	122.64 (18)
O2—C7—N1	121.25 (17)	N3—C19—H19A	109.5
O2—C7—C6	122.64 (17)	N3—C19—H19B	109.5
N1—C7—C6	116.05 (17)	H19A—C19—H19B	109.5
O3—C8—N2	119.69 (18)	N3—C19—H19C	109.5
O3—C8—C9	123.09 (18)	H19A—C19—H19C	109.5
N2—C8—C9	117.21 (17)	H19B—C19—H19C	109.5
C8—C9—H9A	109.5	O4—C20—H20A	109.5
C8—C9—H9B	109.5	O4—C20—H20B	109.5
H9A—C9—H9B	109.5	H20A—C20—H20B	109.5
C8—C9—H9C	109.5	O4—C20—H20C	109.5
H9A—C9—H9C	109.5	H20A—C20—H20C	109.5
H9B—C9—H9C	109.5	H20B—C20—H20C	109.5
O4—C10—N2	111.40 (15)
C7—N1—N2—C8	−84.8 (2)	N1—N2—C10—C11	48.99 (19)
C7—N1—N2—C10	89.2 (2)	C18—N3—C11—C12	0.6 (2)
O1—C1—C2—C3	−177.23 (18)	C19—N3—C11—C12	176.65 (18)
C6—C1—C2—C3	2.8 (3)	C18—N3—C11—C10	−176.91 (16)
C1—C2—C3—C4	0.2 (3)	C19—N3—C11—C10	−0.9 (3)
C2—C3—C4—C5	−1.6 (3)	O4—C10—C11—C12	11.2 (3)
C3—C4—C5—C6	−0.1 (3)	N2—C10—C11—C12	−109.8 (2)
C4—C5—C6—C1	3.0 (3)	O4—C10—C11—N3	−171.84 (16)
C4—C5—C6—C7	−178.81 (18)	N2—C10—C11—N3	67.2 (2)
O1—C1—C6—C5	175.68 (17)	N3—C11—C12—C13	−0.6 (2)
C2—C1—C6—C5	−4.3 (3)	C10—C11—C12—C13	176.68 (18)
O1—C1—C6—C7	−2.6 (3)	C11—C12—C13—C14	−178.7 (2)
C2—C1—C6—C7	177.42 (17)	C11—C12—C13—C18	0.3 (2)
N2—N1—C7—O2	19.8 (3)	C18—C13—C14—C15	−0.2 (3)
N2—N1—C7—C6	−162.92 (15)	C12—C13—C14—C15	178.6 (2)
C5—C6—C7—O2	−163.41 (18)	C13—C14—C15—C16	1.0 (3)
C1—C6—C7—O2	14.8 (3)	C14—C15—C16—C17	−0.2 (3)
C5—C6—C7—N1	19.4 (3)	C15—C16—C17—C18	−1.3 (3)
C1—C6—C7—N1	−162.41 (17)	C11—N3—C18—C17	−179.76 (19)
N1—N2—C8—O3	171.07 (16)	C19—N3—C18—C17	4.0 (3)
C10—N2—C8—O3	−2.5 (3)	C11—N3—C18—C13	−0.4 (2)
N1—N2—C8—C9	−10.1 (2)	C19—N3—C18—C13	−176.59 (17)
C10—N2—C8—C9	176.32 (16)	C16—C17—C18—N3	−178.60 (19)
C20—O4—C10—N2	−71.2 (2)	C16—C17—C18—C13	2.1 (3)
C20—O4—C10—C11	168.97 (15)	C14—C13—C18—N3	179.21 (16)
C8—N2—C10—O4	104.46 (19)	C12—C13—C18—N3	0.1 (2)
N1—N2—C10—O4	−69.42 (19)	C14—C13—C18—C17	−1.4 (3)
C8—N2—C10—C11	−137.13 (17)	C12—C13—C18—C17	179.47 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2	0.87 (1)	1.81 (2)	2.599 (2)	150 (3)
N1—H1n···O3i	0.85 (1)	2.01 (1)	2.812 (2)	157 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2	0.87 (1)	1.81 (2)	2.599 (2)	150 (3)
N1—H1n⋯O3i	0.85 (1)	2.01 (1)	2.812 (2)	157 (2)

Symmetry code: (i) .