(Z)-N'-(4-Hydr-oxy-4-methyl-pentan-2-yl-idene)-2-(8-quinol-yloxy)acetohydrazide.

The title compound, C(17)H(21)N(3)O(3), has a Z configuration about the N=N double bond. The molecular conformation is stabilized by intramolecular N-H⋯O and O-H⋯N hydrogen bonds.

Related literature

For the potential pharmacological and anti­tumor properties of acidamide compounds, see: Harrop et al. (2003 ▶); Ren et al. (2002 ▶). For related structures, see: Lei et al. (2008 ▶); Yang et al. (2007 ▶).

Experimental

Crystal data

C17H21N3O3

M = 315.37

Orthorhombic,

a = 9.3297 (12) Å

b = 10.1621 (13) Å

c = 18.213 (2) Å

V = 1726.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 K

0.20 × 0.18 × 0.15 mm

Data collection

Rigaku Saturn 724+ CCD detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ▶) T min = 0.983, T max = 0.987

9084 measured reflections

1761 independent reflections

1593 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.101

S = 1.04

1761 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrystalClear (Rigaku, 2000 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024957/fj2222sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024957/fj2222Isup2.hkl

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

C17H21N3O3	F(000) = 672
Mr = 315.37	Dx = 1.213 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4517 reflections
a = 9.3297 (12) Å	θ = 2.2–24.9°
b = 10.1621 (13) Å	µ = 0.09 mm−1
c = 18.213 (2) Å	T = 273 K
V = 1726.7 (4) Å3	Block, colorless
Z = 4	0.20 × 0.18 × 0.15 mm

Rigaku Saturn 724+ CCD detector diffractometer	1761 independent reflections
Radiation source: fine-focus sealed tube	1593 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 9 pixels mm-1	θmax = 25.0°, θmin = 2.2°
ω scans	h = −11→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	k = −12→11
Tmin = 0.983, Tmax = 0.987	l = −20→21
9084 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.1302P] where P = (Fo2 + 2Fc2)/3
1761 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	−0.14080 (16)	−0.04549 (14)	0.89142 (8)	0.0517 (4)
O2	−0.0517 (2)	−0.26572 (17)	1.03499 (9)	0.0689 (5)
O3	0.06563 (17)	0.17486 (16)	0.93454 (10)	0.0610 (4)
H3	0.0565	0.1430	0.8934	0.091*
N1	−0.0639 (2)	0.1419 (2)	0.79583 (10)	0.0575 (5)
N2	0.03984 (19)	−0.06920 (18)	0.99886 (10)	0.0520 (4)
H2	0.0391	−0.0095	0.9654	0.062*
N3	0.1400 (2)	−0.06223 (19)	1.05559 (10)	0.0570 (5)
C1	−0.0301 (3)	0.2370 (3)	0.74871 (15)	0.0738 (7)
H1	0.0575	0.2791	0.7551	0.089*
C2	−0.1156 (4)	0.2780 (3)	0.69090 (14)	0.0781 (8)
H2A	−0.0860	0.3458	0.6601	0.094*
C3	−0.2431 (3)	0.2174 (3)	0.68019 (13)	0.0717 (8)
H3A	−0.3014	0.2425	0.6412	0.086*
C4	−0.2882 (3)	0.1155 (2)	0.72835 (12)	0.0578 (6)
C5	−0.4203 (3)	0.0503 (3)	0.72093 (14)	0.0721 (7)
H5	−0.4827	0.0729	0.6832	0.087*
C6	−0.4560 (3)	−0.0455 (3)	0.76902 (15)	0.0750 (7)
H6	−0.5429	−0.0892	0.7632	0.090*
C7	−0.3655 (3)	−0.0816 (3)	0.82796 (13)	0.0628 (6)
H7	−0.3934	−0.1469	0.8607	0.075*
C8	−0.2363 (2)	−0.0194 (2)	0.83633 (11)	0.0478 (5)
C9	−0.1937 (2)	0.0816 (2)	0.78632 (11)	0.0488 (5)
C10	−0.1728 (2)	−0.1518 (2)	0.94005 (12)	0.0542 (5)
H10A	−0.1828	−0.2326	0.9122	0.065*
H10B	−0.2628	−0.1349	0.9649	0.065*
C11	−0.0544 (2)	−0.1672 (2)	0.99604 (11)	0.0492 (5)
C12	0.2509 (3)	0.0078 (2)	1.04208 (14)	0.0640 (6)
C13	0.2906 (3)	0.0687 (3)	0.96876 (16)	0.0684 (7)
H13A	0.2699	0.0051	0.9305	0.082*
H13B	0.3932	0.0841	0.9684	0.082*
C14	0.2151 (3)	0.1985 (3)	0.94902 (19)	0.0747 (8)
C15	0.3571 (4)	0.0213 (3)	1.10411 (19)	0.1010 (12)
H15A	0.4434	−0.0252	1.0920	0.151*
H15B	0.3167	−0.0149	1.1482	0.151*
H15C	0.3786	0.1127	1.1117	0.151*
C16	0.2178 (4)	0.2961 (3)	1.0126 (3)	0.1322 (18)
H16A	0.1606	0.2629	1.0523	0.198*
H16B	0.1797	0.3791	0.9965	0.198*
H16C	0.3147	0.3080	1.0290	0.198*
C17	0.2846 (4)	0.2557 (5)	0.8806 (3)	0.156 (2)
H17A	0.2352	0.3346	0.8665	0.234*
H17B	0.2792	0.1927	0.8413	0.234*
H17C	0.3832	0.2757	0.8906	0.234*

	U11	U22	U33	U12	U13	U23
O1	0.0499 (8)	0.0465 (8)	0.0587 (8)	−0.0073 (7)	−0.0036 (7)	0.0125 (7)
O2	0.0794 (11)	0.0569 (9)	0.0705 (10)	−0.0125 (9)	−0.0105 (9)	0.0225 (8)
O3	0.0504 (8)	0.0505 (9)	0.0819 (10)	−0.0052 (7)	−0.0098 (8)	0.0055 (8)
N1	0.0578 (11)	0.0573 (11)	0.0576 (10)	−0.0058 (10)	0.0067 (9)	0.0118 (9)
N2	0.0524 (10)	0.0476 (9)	0.0559 (9)	−0.0032 (8)	−0.0013 (8)	0.0081 (8)
N3	0.0623 (11)	0.0507 (10)	0.0580 (10)	−0.0003 (9)	−0.0067 (9)	−0.0015 (9)
C1	0.0736 (17)	0.0745 (17)	0.0733 (15)	−0.0074 (14)	0.0140 (14)	0.0225 (14)
C2	0.089 (2)	0.0799 (18)	0.0652 (15)	0.0027 (17)	0.0173 (15)	0.0288 (14)
C3	0.086 (2)	0.0785 (17)	0.0504 (12)	0.0184 (16)	0.0044 (13)	0.0145 (12)
C4	0.0641 (14)	0.0624 (14)	0.0468 (11)	0.0124 (11)	0.0033 (10)	−0.0003 (10)
C5	0.0668 (15)	0.0862 (19)	0.0634 (13)	0.0068 (15)	−0.0140 (12)	0.0047 (15)
C6	0.0607 (14)	0.0828 (18)	0.0814 (16)	−0.0112 (14)	−0.0151 (13)	0.0023 (15)
C7	0.0557 (14)	0.0650 (14)	0.0677 (13)	−0.0069 (12)	−0.0026 (11)	0.0073 (12)
C8	0.0501 (11)	0.0445 (10)	0.0487 (10)	0.0018 (9)	0.0024 (9)	−0.0001 (8)
C9	0.0541 (12)	0.0448 (10)	0.0475 (10)	0.0065 (10)	0.0069 (9)	−0.0008 (9)
C10	0.0549 (12)	0.0460 (11)	0.0616 (12)	−0.0079 (10)	0.0025 (10)	0.0130 (10)
C11	0.0518 (11)	0.0444 (11)	0.0513 (10)	−0.0004 (10)	0.0060 (9)	0.0059 (9)
C12	0.0616 (13)	0.0463 (11)	0.0839 (15)	0.0000 (11)	−0.0131 (13)	0.0044 (11)
C13	0.0457 (12)	0.0603 (13)	0.0992 (17)	−0.0002 (11)	−0.0014 (13)	0.0088 (14)
C14	0.0490 (13)	0.0541 (13)	0.121 (2)	−0.0120 (11)	−0.0157 (15)	0.0222 (15)
C15	0.105 (3)	0.0767 (19)	0.121 (2)	−0.0196 (19)	−0.051 (2)	0.0065 (19)
C16	0.100 (3)	0.0574 (17)	0.239 (5)	0.0046 (17)	−0.081 (3)	−0.032 (2)
C17	0.064 (2)	0.174 (4)	0.231 (5)	−0.028 (2)	−0.006 (3)	0.137 (4)

O1—C8	1.368 (2)	C7—C8	1.370 (3)
O1—C10	1.429 (2)	C7—H7	0.9300
O2—C11	1.228 (3)	C8—C9	1.429 (3)
O3—C14	1.440 (3)	C10—C11	1.512 (3)
O3—H3	0.8200	C10—H10A	0.9700
N1—C1	1.331 (3)	C10—H10B	0.9700
N1—C9	1.368 (3)	C12—C15	1.508 (4)
N2—C11	1.329 (3)	C12—C13	1.518 (4)
N2—N3	1.395 (3)	C13—C14	1.538 (4)
N2—H2	0.8600	C13—H13A	0.9700
N3—C12	1.280 (3)	C13—H13B	0.9700
C1—C2	1.385 (4)	C14—C17	1.520 (5)
C1—H1	0.9300	C14—C16	1.525 (5)
C2—C3	1.354 (4)	C15—H15A	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C3—C4	1.421 (4)	C15—H15C	0.9600
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.406 (4)	C16—H16B	0.9600
C4—C9	1.418 (3)	C16—H16C	0.9600
C5—C6	1.351 (4)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—C7	1.414 (4)	C17—H17C	0.9600
C6—H6	0.9300
C8—O1—C10	117.74 (16)	C11—C10—H10B	109.6
C14—O3—H3	109.5	H10A—C10—H10B	108.2
C1—N1—C9	117.0 (2)	O2—C11—N2	125.1 (2)
C11—N2—N3	120.64 (17)	O2—C11—C10	119.26 (19)
C11—N2—H2	119.7	N2—C11—C10	115.61 (17)
N3—N2—H2	119.7	N3—C12—C15	115.9 (2)
C12—N3—N2	115.31 (18)	N3—C12—C13	126.4 (2)
N1—C1—C2	124.9 (3)	C15—C12—C13	117.5 (2)
N1—C1—H1	117.5	C12—C13—C14	116.3 (2)
C2—C1—H1	117.5	C12—C13—H13A	108.2
C3—C2—C1	118.6 (3)	C14—C13—H13A	108.2
C3—C2—H2A	120.7	C12—C13—H13B	108.2
C1—C2—H2A	120.7	C14—C13—H13B	108.2
C2—C3—C4	120.2 (2)	H13A—C13—H13B	107.4
C2—C3—H3A	119.9	O3—C14—C17	109.0 (3)
C4—C3—H3A	119.9	O3—C14—C16	105.3 (3)
C5—C4—C9	120.2 (2)	C17—C14—C16	111.5 (3)
C5—C4—C3	122.9 (2)	O3—C14—C13	110.1 (2)
C9—C4—C3	116.9 (2)	C17—C14—C13	108.9 (3)
C6—C5—C4	119.6 (2)	C16—C14—C13	111.9 (3)
C6—C5—H5	120.2	C12—C15—H15A	109.5
C4—C5—H5	120.2	C12—C15—H15B	109.5
C5—C6—C7	122.1 (3)	H15A—C15—H15B	109.5
C5—C6—H6	119.0	C12—C15—H15C	109.5
C7—C6—H6	119.0	H15A—C15—H15C	109.5
C8—C7—C6	119.4 (2)	H15B—C15—H15C	109.5
C8—C7—H7	120.3	C14—C16—H16A	109.5
C6—C7—H7	120.3	C14—C16—H16B	109.5
O1—C8—C7	124.42 (19)	H16A—C16—H16B	109.5
O1—C8—C9	115.21 (18)	C14—C16—H16C	109.5
C7—C8—C9	120.4 (2)	H16A—C16—H16C	109.5
N1—C9—C4	122.4 (2)	H16B—C16—H16C	109.5
N1—C9—C8	119.15 (19)	C14—C17—H17A	109.5
C4—C9—C8	118.4 (2)	C14—C17—H17B	109.5
O1—C10—C11	110.08 (17)	H17A—C17—H17B	109.5
O1—C10—H10A	109.6	C14—C17—H17C	109.5
C11—C10—H10A	109.6	H17A—C17—H17C	109.5
O1—C10—H10B	109.6	H17B—C17—H17C	109.5
C11—N2—N3—C12	159.0 (2)	C5—C4—C9—C8	−0.1 (3)
C9—N1—C1—C2	−0.6 (4)	C3—C4—C9—C8	179.3 (2)
N1—C1—C2—C3	−0.5 (5)	O1—C8—C9—N1	1.0 (3)
C1—C2—C3—C4	1.0 (4)	C7—C8—C9—N1	−179.8 (2)
C2—C3—C4—C5	178.9 (3)	O1—C8—C9—C4	−179.09 (18)
C2—C3—C4—C9	−0.4 (3)	C7—C8—C9—C4	0.1 (3)
C9—C4—C5—C6	−0.5 (4)	C8—O1—C10—C11	178.94 (17)
C3—C4—C5—C6	−179.8 (3)	N3—N2—C11—O2	−9.8 (3)
C4—C5—C6—C7	1.1 (4)	N3—N2—C11—C10	169.88 (18)
C5—C6—C7—C8	−1.1 (4)	O1—C10—C11—O2	−168.6 (2)
C10—O1—C8—C7	5.2 (3)	O1—C10—C11—N2	11.7 (3)
C10—O1—C8—C9	−175.65 (17)	N2—N3—C12—C15	177.3 (2)
C6—C7—C8—O1	179.5 (2)	N2—N3—C12—C13	−7.7 (3)
C6—C7—C8—C9	0.4 (3)	N3—C12—C13—C14	81.1 (3)
C1—N1—C9—C4	1.3 (3)	C15—C12—C13—C14	−104.0 (3)
C1—N1—C9—C8	−178.8 (2)	C12—C13—C14—O3	−69.5 (3)
C5—C4—C9—N1	179.8 (2)	C12—C13—C14—C17	171.0 (3)
C3—C4—C9—N1	−0.8 (3)	C12—C13—C14—C16	47.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.82	2.10	2.820 (3)	146
N2—H2···O3	0.86	1.97	2.753 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1	0.82	2.10	2.820 (3)	146
N2—H2⋯O3	0.86	1.97	2.753 (2)	151