N'-[4-(Dimethyl-amino)benzyl-idene]-3-hydroxy-benzohydrazide.

The title compound, C(16)H(17)N(3)O(2), was synthesized by the reaction of 4-dimethyl-amino-benzaldehyde with 3-hydroxy-benzoic acid hydrazide in methanol. The dihedral angle between the two benzene rings in the mol-ecule is 9.2 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For related literature, see: Akitsu & Einaga (2006 ▶); Bahner et al. (1968 ▶); Butcher et al. (2005 ▶); Hodnett & Mooney (1970 ▶); Merchant & Chothia (1970 ▶); Pradeep (2005 ▶); Sigman & Jacobsen (1998 ▶).

Experimental

Crystal data

C16H17N3O2

M = 283.33

Monoclinic,

a = 13.397 (3) Å

b = 9.663 (2) Å

c = 11.183 (2) Å

β = 101.97 (3)°

V = 1416.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.28 × 0.27 × 0.27 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.976

11531 measured reflections

3094 independent reflections

2579 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.05

3094 reflections

196 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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/S160053680800130X/su2040sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800130X/su2040Isup2.hkl

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

C16H17N3O2	F000 = 600
Mr = 283.33	Dx = 1.329 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4593 reflections
a = 13.397 (3) Å	θ = 2.5–27.7º
b = 9.663 (2) Å	µ = 0.09 mm−1
c = 11.183 (2) Å	T = 298 (2) K
β = 101.97 (3)º	Block, yellow
V = 1416.2 (5) Å3	0.28 × 0.27 × 0.27 mm
Z = 4

Bruker SMART APEX area-detector diffractometer	3094 independent reflections
Radiation source: fine-focus sealed tube	2579 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −16→17
Tmin = 0.975, Tmax = 0.976	k = −12→12
11531 measured reflections	l = −14→14

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0773P)2 + 0.1729P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3094 reflections	Δρmax = 0.21 e Å−3
196 parameters	Δρmin = −0.29 e Å−3
1 restraint	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.

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	0.51231 (8)	0.27675 (11)	0.29293 (9)	0.0574 (3)
O2	0.28657 (7)	0.69755 (10)	0.22473 (9)	0.0486 (3)
H2	0.3315	0.7006	0.1849	0.073*
N1	0.97117 (10)	−0.30631 (15)	0.63913 (13)	0.0654 (4)
N2	0.60441 (8)	0.13189 (10)	0.48763 (10)	0.0416 (3)
N3	0.52359 (8)	0.22033 (11)	0.49046 (10)	0.0420 (3)
C1	0.72192 (9)	−0.03254 (12)	0.59700 (11)	0.0379 (3)
C2	0.78863 (10)	−0.03161 (13)	0.51647 (11)	0.0430 (3)
H2A	0.7774	0.0302	0.4513	0.052*
C3	0.87041 (10)	−0.11981 (14)	0.53134 (12)	0.0445 (3)
H3	0.9138	−0.1157	0.4764	0.053*
C4	0.89036 (9)	−0.21613 (13)	0.62715 (12)	0.0425 (3)
C5	0.82405 (10)	−0.21577 (14)	0.70911 (12)	0.0456 (3)
H5	0.8352	−0.2770	0.7747	0.055*
C6	0.74284 (10)	−0.12595 (14)	0.69358 (11)	0.0424 (3)
H6	0.7004	−0.1277	0.7496	0.051*
C7	0.99119 (16)	−0.4061 (2)	0.73523 (17)	0.0793 (6)
H7A	1.0129	−0.3597	0.8121	0.119*
H7B	1.0439	−0.4679	0.7219	0.119*
H7C	0.9302	−0.4578	0.7363	0.119*
C8	1.04154 (15)	−0.2992 (2)	0.5584 (2)	0.0903 (7)
H8A	1.0063	−0.3194	0.4764	0.135*
H8B	1.0952	−0.3655	0.5835	0.135*
H8C	1.0702	−0.2079	0.5612	0.135*
C9	0.63422 (9)	0.05897 (13)	0.58348 (11)	0.0411 (3)
H9	0.5988	0.0645	0.6466	0.049*
C10	0.48449 (9)	0.29458 (12)	0.38962 (12)	0.0397 (3)
C11	0.40510 (9)	0.39961 (12)	0.40150 (11)	0.0375 (3)
C12	0.38258 (9)	0.49733 (12)	0.30887 (11)	0.0375 (3)
H12	0.4168	0.4954	0.2446	0.045*
C13	0.30939 (9)	0.59770 (12)	0.31174 (11)	0.0380 (3)
C14	0.25681 (10)	0.59887 (14)	0.40629 (12)	0.0453 (3)
H14	0.2067	0.6651	0.4080	0.054*
C15	0.27927 (11)	0.50121 (16)	0.49776 (13)	0.0530 (4)
H15	0.2440	0.5021	0.5611	0.064*
C16	0.35350 (10)	0.40181 (14)	0.49689 (12)	0.0469 (3)
H16	0.3686	0.3372	0.5596	0.056*
H3A	0.5095 (14)	0.2388 (19)	0.5637 (11)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0646 (6)	0.0592 (6)	0.0572 (6)	0.0197 (5)	0.0327 (5)	0.0044 (5)
O2	0.0480 (5)	0.0487 (5)	0.0530 (6)	0.0081 (4)	0.0192 (4)	0.0094 (4)
N1	0.0552 (7)	0.0751 (9)	0.0698 (8)	0.0289 (7)	0.0219 (6)	0.0220 (7)
N2	0.0369 (5)	0.0388 (6)	0.0501 (6)	0.0050 (4)	0.0114 (4)	−0.0082 (4)
N3	0.0380 (5)	0.0417 (6)	0.0485 (6)	0.0072 (4)	0.0137 (5)	−0.0065 (5)
C1	0.0368 (6)	0.0382 (6)	0.0391 (6)	−0.0001 (5)	0.0087 (5)	−0.0057 (5)
C2	0.0452 (7)	0.0451 (7)	0.0400 (6)	0.0056 (5)	0.0115 (5)	0.0069 (5)
C3	0.0427 (7)	0.0535 (8)	0.0407 (7)	0.0056 (5)	0.0162 (5)	0.0024 (5)
C4	0.0388 (6)	0.0447 (7)	0.0432 (7)	0.0046 (5)	0.0067 (5)	0.0001 (5)
C5	0.0467 (7)	0.0504 (7)	0.0397 (7)	0.0023 (6)	0.0085 (5)	0.0086 (5)
C6	0.0428 (7)	0.0499 (7)	0.0373 (6)	−0.0026 (5)	0.0149 (5)	−0.0027 (5)
C7	0.0834 (12)	0.0834 (13)	0.0713 (11)	0.0421 (10)	0.0162 (9)	0.0196 (9)
C8	0.0656 (11)	0.1028 (15)	0.1139 (16)	0.0410 (11)	0.0449 (11)	0.0305 (13)
C9	0.0394 (6)	0.0403 (6)	0.0456 (7)	0.0004 (5)	0.0131 (5)	−0.0074 (5)
C10	0.0359 (6)	0.0369 (6)	0.0497 (7)	0.0000 (5)	0.0165 (5)	−0.0046 (5)
C11	0.0332 (6)	0.0371 (6)	0.0442 (7)	−0.0012 (5)	0.0122 (5)	−0.0055 (5)
C12	0.0352 (6)	0.0394 (6)	0.0412 (6)	−0.0024 (5)	0.0156 (5)	−0.0044 (5)
C13	0.0345 (6)	0.0378 (6)	0.0423 (6)	−0.0024 (5)	0.0095 (5)	−0.0018 (5)
C14	0.0393 (6)	0.0472 (7)	0.0530 (7)	0.0094 (5)	0.0182 (5)	−0.0002 (6)
C15	0.0532 (8)	0.0630 (9)	0.0511 (8)	0.0150 (6)	0.0302 (6)	0.0071 (6)
C16	0.0486 (7)	0.0502 (7)	0.0464 (7)	0.0102 (6)	0.0199 (6)	0.0079 (6)

O1—C10	1.2267 (15)	C6—H6	0.9300
O2—C13	1.3593 (15)	C7—H7A	0.9600
O2—H2	0.8200	C7—H7B	0.9600
N1—C4	1.3745 (17)	C7—H7C	0.9600
N1—C7	1.427 (2)	C8—H8A	0.9600
N1—C8	1.436 (2)	C8—H8B	0.9600
N2—C9	1.2757 (16)	C8—H8C	0.9600
N2—N3	1.3848 (14)	C9—H9	0.9300
N3—C10	1.3475 (17)	C10—C11	1.4958 (16)
N3—H3A	0.895 (9)	C11—C16	1.3864 (18)
C1—C6	1.3907 (17)	C11—C12	1.3878 (17)
C1—C2	1.3942 (17)	C12—C13	1.3842 (17)
C1—C9	1.4531 (17)	C12—H12	0.9300
C2—C3	1.3706 (17)	C13—C14	1.3868 (17)
C2—H2A	0.9300	C14—C15	1.3783 (19)
C3—C4	1.4025 (18)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.3841 (18)
C4—C5	1.4025 (19)	C15—H15	0.9300
C5—C6	1.3744 (18)	C16—H16	0.9300
C5—H5	0.9300
C13—O2—H2	109.5	H7B—C7—H7C	109.5
C4—N1—C7	121.53 (13)	N1—C8—H8A	109.5
C4—N1—C8	120.99 (13)	N1—C8—H8B	109.5
C7—N1—C8	117.43 (13)	H8A—C8—H8B	109.5
C9—N2—N3	115.57 (10)	N1—C8—H8C	109.5
C10—N3—N2	118.66 (10)	H8A—C8—H8C	109.5
C10—N3—H3A	122.7 (12)	H8B—C8—H8C	109.5
N2—N3—H3A	117.2 (12)	N2—C9—C1	121.94 (11)
C6—C1—C2	116.93 (11)	N2—C9—H9	119.0
C6—C1—C9	120.27 (11)	C1—C9—H9	119.0
C2—C1—C9	122.80 (11)	O1—C10—N3	121.76 (11)
C3—C2—C1	121.39 (12)	O1—C10—C11	121.68 (12)
C3—C2—H2A	119.3	N3—C10—C11	116.56 (10)
C1—C2—H2A	119.3	C16—C11—C12	119.87 (11)
C2—C3—C4	121.75 (11)	C16—C11—C10	123.77 (11)
C2—C3—H3	119.1	C12—C11—C10	116.35 (10)
C4—C3—H3	119.1	C13—C12—C11	120.32 (10)
N1—C4—C5	122.05 (12)	C13—C12—H12	119.8
N1—C4—C3	121.11 (12)	C11—C12—H12	119.8
C5—C4—C3	116.84 (11)	O2—C13—C12	122.41 (10)
C6—C5—C4	120.73 (12)	O2—C13—C14	117.75 (11)
C6—C5—H5	119.6	C12—C13—C14	119.84 (11)
C4—C5—H5	119.6	C15—C14—C13	119.55 (11)
C5—C6—C1	122.33 (11)	C15—C14—H14	120.2
C5—C6—H6	118.8	C13—C14—H14	120.2
C1—C6—H6	118.8	C14—C15—C16	121.09 (12)
N1—C7—H7A	109.5	C14—C15—H15	119.5
N1—C7—H7B	109.5	C16—C15—H15	119.5
H7A—C7—H7B	109.5	C15—C16—C11	119.32 (12)
N1—C7—H7C	109.5	C15—C16—H16	120.3
H7A—C7—H7C	109.5	C11—C16—H16	120.3

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	2.18	2.8470 (14)	138
O2—H2···N2i	0.82	2.36	3.1008 (16)	150
N3—H3A···O1ii	0.895 (9)	2.561 (11)	3.4172 (16)	160.4 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	2.18	2.8470 (14)	138
O2—H2⋯N2i	0.82	2.36	3.1008 (16)	150
N3—H3A⋯O1ii	0.895 (9)	2.561 (11)	3.4172 (16)	160.4 (16)

Symmetry codes: (i) ; (ii) .