N'-[(1E)-1-(5-Chloro-2-hydroxy-phen-yl)propyl-idene]-4-methoxy-benzohydrazide.

The title compound, C(17)H(17)ClN(2)O(3), has a trans conformation about the C=N double bond and an intra-molecular O-H⋯N occurs. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For further details of the chemistry of the title compound, see Carcelli et al. (1995 ▶); Salem (1998 ▶).

Experimental

Crystal data

C17H17ClN2O3

M = 332.78

Monoclinic,

a = 8.6313 (13) Å

b = 4.9373 (8) Å

c = 19.610 (3) Å

β = 102.359 (3)°

V = 816.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 295 K

0.25 × 0.17 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.940, T max = 0.971

4350 measured reflections

2837 independent reflections

2047 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.098

S = 1.05

2837 reflections

209 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1207 Friedel pairs

Flack parameter: 0.13 (9)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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/S1600536809052878/pk2217sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052878/pk2217Isup2.hkl

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

C17H17ClN2O3	F(000) = 348
Mr = 332.78	Dx = 1.354 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 982 reflections
a = 8.6313 (13) Å	θ = 2.8–21.4°
b = 4.9373 (8) Å	µ = 0.25 mm−1
c = 19.610 (3) Å	T = 295 K
β = 102.359 (3)°	Block, colourless
V = 816.3 (2) Å3	0.25 × 0.17 × 0.12 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	2837 independent reflections
Radiation source: fine-focus sealed tube	2047 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→7
Tmin = 0.940, Tmax = 0.971	k = −5→5
4350 measured reflections	l = −15→23

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0334P)2 + 0.0867P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2837 reflections	Δρmax = 0.13 e Å−3
209 parameters	Δρmin = −0.19 e Å−3
1 restraint	Absolute structure: Flack (1983), 1207 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.13 (9)

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
Cl1	0.70397 (10)	0.5956 (2)	0.50973 (4)	0.0773 (3)
O1	0.5785 (2)	0.0599 (5)	0.75880 (12)	0.0668 (6)
H1	0.5050	0.1302	0.7727	0.100*
O2	0.2166 (3)	0.0098 (4)	0.82097 (12)	0.0690 (7)
O3	−0.3408 (3)	0.4662 (5)	0.95022 (12)	0.0740 (7)
N1	0.2158 (3)	0.4370 (5)	0.78114 (13)	0.0541 (7)
H1A	0.1733	0.5953	0.7763	0.065*
N2	0.3433 (3)	0.3712 (5)	0.75179 (13)	0.0528 (7)
C1	0.6042 (4)	0.1967 (6)	0.70286 (16)	0.0529 (8)
C2	0.5080 (3)	0.4145 (6)	0.67236 (15)	0.0451 (7)
C3	0.5434 (3)	0.5345 (7)	0.61244 (14)	0.0494 (8)
H3	0.4814	0.6771	0.5909	0.059*
C4	0.6678 (4)	0.4446 (7)	0.58540 (16)	0.0552 (9)
C5	0.7620 (4)	0.2322 (8)	0.61561 (19)	0.0635 (9)
H5	0.8454	0.1714	0.5965	0.076*
C6	0.7307 (3)	0.1117 (8)	0.67442 (18)	0.0639 (9)
H6	0.7951	−0.0289	0.6956	0.077*
C7	0.3708 (3)	0.5104 (6)	0.69966 (15)	0.0452 (7)
C8	0.1611 (4)	0.2390 (7)	0.81801 (16)	0.0520 (8)
C9	0.0293 (3)	0.3162 (6)	0.85165 (14)	0.0445 (7)
C10	−0.0777 (4)	0.5202 (7)	0.82750 (16)	0.0574 (9)
H10	−0.0642	0.6230	0.7895	0.069*
C11	−0.2041 (3)	0.5764 (7)	0.85793 (15)	0.0587 (8)
H11	−0.2762	0.7119	0.8401	0.070*
C12	−0.2215 (4)	0.4274 (7)	0.91544 (15)	0.0525 (8)
C13	−0.1146 (4)	0.2243 (7)	0.94116 (16)	0.0577 (9)
H13	−0.1264	0.1251	0.9800	0.069*
C14	0.0089 (4)	0.1689 (6)	0.90945 (15)	0.0544 (8)
H14	0.0799	0.0310	0.9268	0.065*
C15	0.2677 (3)	0.7379 (7)	0.66588 (15)	0.0536 (8)
H15A	0.3300	0.8609	0.6440	0.064*
H15B	0.2283	0.8380	0.7012	0.064*
C16	0.1279 (4)	0.6325 (11)	0.61111 (19)	0.0939 (13)
H16A	0.1665	0.5444	0.5744	0.141*
H16B	0.0608	0.7813	0.5921	0.141*
H16C	0.0684	0.5056	0.6323	0.141*
C17	−0.4560 (4)	0.6733 (9)	0.9258 (2)	0.0895 (13)
H17A	−0.4043	0.8464	0.9289	0.134*
H17B	−0.5342	0.6742	0.9540	0.134*
H17C	−0.5065	0.6377	0.8780	0.134*

	U11	U22	U33	U12	U13	U23
Cl1	0.0774 (6)	0.0948 (7)	0.0677 (5)	−0.0054 (6)	0.0335 (4)	−0.0015 (6)
O1	0.0718 (15)	0.0543 (16)	0.0764 (14)	0.0118 (13)	0.0205 (12)	0.0138 (14)
O2	0.1008 (18)	0.0361 (15)	0.0827 (16)	0.0085 (12)	0.0477 (15)	0.0034 (12)
O3	0.0694 (15)	0.085 (2)	0.0769 (16)	0.0074 (14)	0.0363 (13)	0.0030 (14)
N1	0.0677 (17)	0.0358 (15)	0.0667 (16)	0.0042 (13)	0.0319 (14)	0.0035 (13)
N2	0.0639 (17)	0.0403 (16)	0.0606 (16)	0.0001 (13)	0.0278 (14)	0.0000 (14)
C1	0.0542 (19)	0.041 (2)	0.062 (2)	−0.0043 (16)	0.0091 (17)	−0.0025 (17)
C2	0.0453 (17)	0.0380 (17)	0.0522 (18)	−0.0049 (14)	0.0108 (14)	−0.0051 (16)
C3	0.0473 (17)	0.050 (2)	0.0519 (17)	−0.0014 (16)	0.0116 (14)	−0.0026 (16)
C4	0.0522 (18)	0.059 (2)	0.0562 (19)	−0.0078 (18)	0.0162 (16)	−0.0090 (18)
C5	0.0491 (19)	0.056 (2)	0.089 (3)	0.0005 (19)	0.0211 (19)	−0.013 (2)
C6	0.0515 (18)	0.052 (2)	0.087 (2)	0.0091 (18)	0.0129 (17)	−0.004 (2)
C7	0.0491 (17)	0.0347 (17)	0.0529 (18)	−0.0037 (14)	0.0134 (15)	−0.0061 (15)
C8	0.069 (2)	0.0380 (19)	0.053 (2)	−0.0046 (18)	0.0224 (17)	−0.0020 (16)
C9	0.0575 (19)	0.0341 (17)	0.0447 (18)	−0.0021 (15)	0.0169 (15)	−0.0039 (14)
C10	0.069 (2)	0.053 (2)	0.0545 (18)	0.0021 (18)	0.0208 (16)	0.0090 (17)
C11	0.0565 (18)	0.057 (2)	0.0637 (19)	0.007 (2)	0.0151 (16)	0.001 (2)
C12	0.0558 (19)	0.055 (2)	0.0492 (18)	−0.0047 (18)	0.0173 (16)	−0.0069 (18)
C13	0.072 (2)	0.053 (2)	0.0514 (19)	0.0018 (19)	0.0227 (17)	0.0089 (17)
C14	0.069 (2)	0.046 (2)	0.0505 (18)	0.0060 (16)	0.0188 (16)	0.0054 (16)
C15	0.057 (2)	0.0478 (19)	0.062 (2)	0.0037 (17)	0.0244 (17)	0.0041 (17)
C16	0.056 (2)	0.113 (4)	0.106 (3)	−0.006 (2)	0.004 (2)	0.010 (3)
C17	0.074 (3)	0.099 (4)	0.104 (3)	0.013 (3)	0.039 (2)	−0.002 (3)

Cl1—C4	1.747 (3)	C8—C9	1.481 (4)
O1—C1	1.346 (3)	C9—C10	1.380 (4)
O1—H1	0.8200	C9—C14	1.389 (4)
O2—C8	1.225 (4)	C10—C11	1.379 (4)
O3—C12	1.364 (3)	C10—H10	0.9300
O3—C17	1.435 (4)	C11—C12	1.381 (4)
N1—C8	1.359 (4)	C11—H11	0.9300
N1—N2	1.385 (3)	C12—C13	1.383 (4)
N1—H1A	0.8600	C13—C14	1.372 (4)
N2—C7	1.295 (3)	C13—H13	0.9300
C1—C6	1.393 (4)	C14—H14	0.9300
C1—C2	1.411 (4)	C15—C16	1.525 (4)
C2—C3	1.407 (4)	C15—H15A	0.9700
C2—C7	1.478 (4)	C15—H15B	0.9700
C3—C4	1.369 (4)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.381 (5)	C16—H16C	0.9600
C5—C6	1.375 (5)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—C15	1.497 (4)
C1—O1—H1	109.5	C11—C10—C9	122.1 (3)
C12—O3—C17	118.4 (3)	C11—C10—H10	118.9
C8—N1—N2	116.7 (2)	C9—C10—H10	118.9
C8—N1—H1A	121.6	C10—C11—C12	118.7 (3)
N2—N1—H1A	121.6	C10—C11—H11	120.6
C7—N2—N1	120.0 (3)	C12—C11—H11	120.6
O1—C1—C6	117.1 (3)	O3—C12—C11	124.0 (3)
O1—C1—C2	122.9 (3)	O3—C12—C13	115.8 (3)
C6—C1—C2	120.0 (3)	C11—C12—C13	120.2 (3)
C3—C2—C1	117.5 (3)	C14—C13—C12	120.1 (3)
C3—C2—C7	120.2 (3)	C14—C13—H13	119.9
C1—C2—C7	122.3 (3)	C12—C13—H13	119.9
C4—C3—C2	121.1 (3)	C13—C14—C9	120.8 (3)
C4—C3—H3	119.5	C13—C14—H14	119.6
C2—C3—H3	119.5	C9—C14—H14	119.6
C3—C4—C5	121.2 (3)	C7—C15—C16	111.2 (3)
C3—C4—Cl1	119.2 (3)	C7—C15—H15A	109.4
C5—C4—Cl1	119.5 (3)	C16—C15—H15A	109.4
C6—C5—C4	119.0 (3)	C7—C15—H15B	109.4
C6—C5—H5	120.5	C16—C15—H15B	109.4
C4—C5—H5	120.5	H15A—C15—H15B	108.0
C5—C6—C1	121.2 (3)	C15—C16—H16A	109.5
C5—C6—H6	119.4	C15—C16—H16B	109.5
C1—C6—H6	119.4	H16A—C16—H16B	109.5
N2—C7—C2	114.3 (3)	C15—C16—H16C	109.5
N2—C7—C15	123.8 (3)	H16A—C16—H16C	109.5
C2—C7—C15	121.8 (3)	H16B—C16—H16C	109.5
O2—C8—N1	120.8 (3)	O3—C17—H17A	109.5
O2—C8—C9	123.1 (3)	O3—C17—H17B	109.5
N1—C8—C9	116.0 (3)	H17A—C17—H17B	109.5
C10—C9—C14	118.0 (3)	O3—C17—H17C	109.5
C10—C9—C8	123.8 (3)	H17A—C17—H17C	109.5
C14—C9—C8	118.1 (3)	H17B—C17—H17C	109.5
C8—N1—N2—C7	158.5 (3)	N2—N1—C8—O2	−4.4 (5)
O1—C1—C2—C3	−177.6 (3)	N2—N1—C8—C9	177.4 (3)
C6—C1—C2—C3	1.3 (4)	O2—C8—C9—C10	−151.6 (3)
O1—C1—C2—C7	0.1 (4)	N1—C8—C9—C10	26.5 (4)
C6—C1—C2—C7	179.0 (3)	O2—C8—C9—C14	26.0 (5)
C1—C2—C3—C4	−0.7 (4)	N1—C8—C9—C14	−155.8 (3)
C7—C2—C3—C4	−178.5 (3)	C14—C9—C10—C11	−1.4 (4)
C2—C3—C4—C5	0.5 (5)	C8—C9—C10—C11	176.3 (3)
C2—C3—C4—Cl1	178.6 (2)	C9—C10—C11—C12	1.6 (5)
C3—C4—C5—C6	−0.8 (5)	C17—O3—C12—C11	0.3 (5)
Cl1—C4—C5—C6	−178.8 (3)	C17—O3—C12—C13	−179.7 (3)
C4—C5—C6—C1	1.3 (5)	C10—C11—C12—O3	179.4 (3)
O1—C1—C6—C5	177.4 (3)	C10—C11—C12—C13	−0.7 (5)
C2—C1—C6—C5	−1.6 (5)	O3—C12—C13—C14	179.6 (3)
N1—N2—C7—C2	−178.6 (2)	C11—C12—C13—C14	−0.3 (5)
N1—N2—C7—C15	−2.6 (4)	C12—C13—C14—C9	0.5 (5)
C3—C2—C7—N2	175.1 (3)	C10—C9—C14—C13	0.3 (4)
C1—C2—C7—N2	−2.6 (4)	C8—C9—C14—C13	−177.5 (3)
C3—C2—C7—C15	−1.0 (4)	N2—C7—C15—C16	−84.3 (4)
C1—C2—C7—C15	−178.7 (3)	C2—C7—C15—C16	91.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.81	2.526 (3)	145
N1—H1A···O2i	0.86	2.23	2.934 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.82	1.81	2.526 (3)	145
N1—H1A⋯O2i	0.86	2.23	2.934 (3)	140

Symmetry code: (i) .