N'-(2-Hydroxy-benzyl-idene)-4-methoxy-benzohydrazide.

The title Schiff base compound, C(15)H(14)N(2)O(3), was derived from the condensation reaction of salicylaldehyde with 4-methoxy-benzohydrazide. The dihedral angle between the two benzene rings is 2.5 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For related structures, see: Tang (2006 ▶, 2007a ▶,b ▶,c ▶,d ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14N2O3

M = 270.28

Monoclinic,

a = 16.283 (4) Å

b = 5.1876 (12) Å

c = 16.303 (4) Å

β = 108.093 (2)°

V = 1309.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.23 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.984

7166 measured reflections

2862 independent reflections

2288 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.03

2862 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008088/sj2477sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008088/sj2477Isup2.hkl

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

C15H14N2O3	F000 = 568
Mr = 270.28	Dx = 1.371 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2841 reflections
a = 16.283 (4) Å	θ = 2.5–28.4º
b = 5.1876 (12) Å	µ = 0.10 mm−1
c = 16.303 (4) Å	T = 298 (2) K
β = 108.093 (2)º	Cut from a needle, colorless
V = 1309.0 (5) Å3	0.23 × 0.20 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2862 independent reflections
Radiation source: fine-focus sealed tube	2288 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −20→17
Tmin = 0.978, Tmax = 0.984	k = −6→5
7166 measured reflections	l = −20→20

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0543P)2 + 0.1695P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.111	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.19 e Å−3
2862 reflections	Δρmin = −0.14 e Å−3
183 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0102 (19)
Secondary atom site location: difference Fourier map

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	0.28687 (6)	0.79939 (18)	0.04446 (6)	0.0589 (3)
H1	0.2415	0.8168	0.0558	0.071*
O2	0.07668 (6)	0.61484 (17)	0.09720 (6)	0.0513 (3)
O3	−0.28125 (6)	0.8712 (2)	0.15298 (7)	0.0603 (3)
N1	0.18099 (6)	1.0151 (2)	0.11628 (7)	0.0458 (3)
N2	0.09898 (6)	1.0412 (2)	0.12266 (7)	0.0458 (3)
H2	0.0786	1.2025	0.1239	0.055*
C1	0.32018 (7)	1.1824 (2)	0.13304 (8)	0.0418 (3)
C2	0.34309 (8)	0.9849 (2)	0.08499 (8)	0.0447 (3)
C3	0.42580 (9)	0.9783 (3)	0.07764 (9)	0.0539 (3)
H3	0.4407	0.8497	0.0451	0.065*
C4	0.48579 (9)	1.1612 (3)	0.11825 (9)	0.0564 (4)
H4A	0.5410	1.1548	0.1129	0.068*
C5	0.46509 (9)	1.3546 (3)	0.16693 (9)	0.0559 (4)
H5	0.5063	1.4758	0.1950	0.067*
C6	0.38275 (8)	1.3652 (3)	0.17323 (8)	0.0497 (3)
H6	0.3685	1.4972	0.2050	0.060*
C7	0.23383 (8)	1.2025 (2)	0.14075 (8)	0.0448 (3)
H7	0.2172	1.3510	0.1634	0.054*
C8	0.04904 (7)	0.8257 (2)	0.11109 (7)	0.0393 (3)
C9	−0.03888 (7)	0.8543 (2)	0.11895 (7)	0.0376 (3)
C10	−0.06242 (8)	1.0470 (2)	0.16743 (8)	0.0439 (3)
H10	−0.0232	1.1763	0.1929	0.053*
C11	−0.14321 (8)	1.0465 (2)	0.17758 (8)	0.0475 (3)
H11	−0.1580	1.1738	0.2106	0.057*
C12	−0.20273 (8)	0.8575 (2)	0.13885 (8)	0.0438 (3)
C13	−0.18097 (8)	0.6676 (2)	0.08943 (8)	0.0465 (3)
H13	−0.2209	0.5417	0.0626	0.056*
C14	−0.09942 (8)	0.6672 (2)	0.08042 (8)	0.0436 (3)
H14	−0.0847	0.5386	0.0478	0.052*
C15	−0.33848 (9)	0.6588 (3)	0.12432 (11)	0.0682 (4)
H15A	−0.3531	0.6430	0.0628	0.102*
H15B	−0.3901	0.6869	0.1397	0.102*
H15C	−0.3108	0.5034	0.1511	0.102*

	U11	U22	U33	U12	U13	U23
O1	0.0530 (6)	0.0498 (6)	0.0720 (6)	−0.0030 (4)	0.0166 (5)	−0.0180 (5)
O2	0.0492 (5)	0.0387 (5)	0.0677 (6)	0.0032 (4)	0.0206 (4)	−0.0064 (4)
O3	0.0521 (6)	0.0612 (6)	0.0769 (7)	−0.0039 (5)	0.0339 (5)	−0.0048 (5)
N1	0.0397 (5)	0.0411 (6)	0.0572 (6)	0.0003 (4)	0.0159 (5)	0.0006 (5)
N2	0.0392 (5)	0.0368 (6)	0.0628 (7)	0.0017 (4)	0.0180 (5)	−0.0017 (5)
C1	0.0423 (6)	0.0367 (6)	0.0455 (6)	−0.0002 (5)	0.0123 (5)	0.0029 (5)
C2	0.0471 (7)	0.0398 (7)	0.0455 (7)	0.0003 (5)	0.0118 (5)	0.0016 (5)
C3	0.0568 (8)	0.0536 (8)	0.0565 (8)	0.0054 (6)	0.0250 (6)	−0.0013 (6)
C4	0.0476 (7)	0.0623 (9)	0.0647 (8)	−0.0017 (6)	0.0253 (6)	0.0080 (7)
C5	0.0494 (7)	0.0522 (8)	0.0650 (8)	−0.0130 (6)	0.0163 (6)	0.0007 (7)
C6	0.0505 (7)	0.0422 (7)	0.0561 (8)	−0.0051 (6)	0.0163 (6)	−0.0040 (6)
C7	0.0451 (7)	0.0390 (7)	0.0499 (7)	0.0019 (5)	0.0141 (5)	−0.0020 (5)
C8	0.0421 (6)	0.0361 (6)	0.0382 (6)	0.0018 (5)	0.0102 (5)	−0.0005 (5)
C9	0.0418 (6)	0.0334 (6)	0.0368 (6)	0.0006 (5)	0.0111 (5)	0.0014 (4)
C10	0.0487 (7)	0.0356 (6)	0.0466 (7)	−0.0034 (5)	0.0134 (5)	−0.0069 (5)
C11	0.0556 (7)	0.0409 (7)	0.0505 (7)	0.0012 (6)	0.0229 (6)	−0.0074 (5)
C12	0.0444 (6)	0.0449 (7)	0.0455 (6)	0.0015 (5)	0.0187 (5)	0.0046 (5)
C13	0.0456 (7)	0.0434 (7)	0.0494 (7)	−0.0079 (5)	0.0131 (5)	−0.0063 (5)
C14	0.0490 (7)	0.0380 (7)	0.0451 (6)	−0.0019 (5)	0.0165 (5)	−0.0068 (5)
C15	0.0492 (8)	0.0726 (11)	0.0883 (11)	−0.0098 (7)	0.0293 (8)	0.0025 (8)

O1—C2	1.3509 (15)	C5—H5	0.9300
O1—H1	0.8200	C6—H6	0.9300
O2—C8	1.2303 (14)	C7—H7	0.9300
O3—C12	1.3695 (14)	C8—C9	1.4839 (16)
O3—C15	1.4248 (17)	C9—C14	1.3870 (16)
N1—C7	1.2773 (16)	C9—C10	1.3997 (16)
N1—N2	1.3780 (14)	C10—C11	1.3759 (17)
N2—C8	1.3604 (15)	C10—H10	0.9300
N2—H2	0.9000	C11—C12	1.3854 (17)
C1—C6	1.3974 (17)	C11—H11	0.9300
C1—C2	1.4085 (17)	C12—C13	1.3864 (17)
C1—C7	1.4538 (16)	C13—C14	1.3805 (17)
C2—C3	1.3891 (17)	C13—H13	0.9300
C3—C4	1.3750 (19)	C14—H14	0.9300
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.384 (2)	C15—H15B	0.9600
C4—H4A	0.9300	C15—H15C	0.9600
C5—C6	1.3772 (18)
C2—O1—H1	109.4	O2—C8—N2	121.27 (11)
C12—O3—C15	117.01 (11)	O2—C8—C9	121.51 (10)
C7—N1—N2	118.44 (11)	N2—C8—C9	117.19 (10)
C8—N2—N1	117.41 (10)	C14—C9—C10	118.34 (11)
C8—N2—H2	123.9	C14—C9—C8	117.39 (10)
N1—N2—H2	117.6	C10—C9—C8	124.13 (10)
C6—C1—C2	118.30 (11)	C11—C10—C9	120.40 (11)
C6—C1—C7	119.64 (11)	C11—C10—H10	119.8
C2—C1—C7	122.06 (11)	C9—C10—H10	119.8
O1—C2—C3	117.92 (11)	C10—C11—C12	120.42 (11)
O1—C2—C1	122.26 (11)	C10—C11—H11	119.8
C3—C2—C1	119.82 (12)	C12—C11—H11	119.8
C4—C3—C2	120.29 (13)	O3—C12—C11	116.36 (11)
C4—C3—H3	119.9	O3—C12—C13	123.72 (11)
C2—C3—H3	119.9	C11—C12—C13	119.92 (11)
C3—C4—C5	120.86 (12)	C14—C13—C12	119.39 (11)
C3—C4—H4A	119.6	C14—C13—H13	120.3
C5—C4—H4A	119.6	C12—C13—H13	120.3
C6—C5—C4	119.20 (12)	C13—C14—C9	121.52 (11)
C6—C5—H5	120.4	C13—C14—H14	119.2
C4—C5—H5	120.4	C9—C14—H14	119.2
C5—C6—C1	121.51 (12)	O3—C15—H15A	109.5
C5—C6—H6	119.2	O3—C15—H15B	109.5
C1—C6—H6	119.2	H15A—C15—H15B	109.5
N1—C7—C1	119.60 (11)	O3—C15—H15C	109.5
N1—C7—H7	120.2	H15A—C15—H15C	109.5
C1—C7—H7	120.2	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.90	2.18	3.0112 (15)	153
O1—H1···N1	0.82	1.90	2.6171 (14)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.90	2.18	3.0112 (15)	153
O1—H1⋯N1	0.82	1.90	2.6171 (14)	146

Symmetry code: (i) .