2-[2-(2-Carb-oxy-phen-yl)hydrazinyl-idene]-3-oxo-N-phenyl-butyramide.

In the title compound, C(17)H(15)N(3)O(4), the mol-ecule is in the keto-hydrazone form. Intra-molecular N-H⋯O hydrogen bonds ensure that the mol-ecule is nearly planar (r.m.s. deviation of non-H atoms is 0.098 Å), with the two benzene rings forming a dihedral angle of 10.04 (2)°. In the crystal, inversion dimers are formed via pairs of O-H⋯O hydrogen bonds involving the -CO(2)H groups.

Related literature

For general background to the properties of organic pigments, see: Schmidt et al. (2007 ▶); Barrow et al. (2002 ▶). For related structures, see: van de Streek et al. (2009 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H15N3O4

M = 325.32

Monoclinic,

a = 15.5731 (16) Å

b = 5.3292 (5) Å

c = 18.7731 (19) Å

β = 99.246 (1)°

V = 1537.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.50 × 0.30 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.951, T max = 0.979

7277 measured reflections

2724 independent reflections

1459 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.137

S = 1.02

2724 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048173/pk2357sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048173/pk2357Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048173/pk2357Isup3.cml

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

C17H15N3O4	F(000) = 680
Mr = 325.32	Dx = 1.405 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1353 reflections
a = 15.5731 (16) Å	θ = 2.7–21.8°
b = 5.3292 (5) Å	µ = 0.10 mm−1
c = 18.7731 (19) Å	T = 298 K
β = 99.246 (1)°	Prism, yellow
V = 1537.8 (3) Å3	0.50 × 0.30 × 0.21 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2724 independent reflections
Radiation source: fine-focus sealed tube	1459 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −18→17
Tmin = 0.951, Tmax = 0.979	k = −6→6
7277 measured reflections	l = −16→22

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.044P)2 + 0.5365P] where P = (Fo2 + 2Fc2)/3
2724 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.17 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 > 2σ(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
N1	0.41408 (14)	0.3850 (5)	0.60735 (12)	0.0434 (7)
H1	0.3974	0.5025	0.5769	0.052*
N2	0.35836 (15)	0.2176 (4)	0.62294 (12)	0.0419 (6)
N3	0.16263 (15)	0.3518 (5)	0.49622 (13)	0.0505 (7)
H3	0.1377	0.2185	0.5086	0.061*
O1	0.15219 (14)	−0.0370 (4)	0.58537 (12)	0.0645 (7)
O2	0.28838 (12)	0.5712 (4)	0.51762 (11)	0.0555 (6)
O3	0.46446 (12)	0.7749 (4)	0.53863 (11)	0.0549 (6)
O4	0.60410 (12)	0.8767 (4)	0.55453 (10)	0.0512 (6)
H4	0.5857	0.9845	0.5248	0.077*
C1	0.2678 (2)	−0.1513 (6)	0.67626 (18)	0.0644 (10)
H1A	0.2247	−0.2606	0.6908	0.097*
H1B	0.2911	−0.0448	0.7159	0.097*
H1C	0.3137	−0.2498	0.6620	0.097*
C2	0.2268 (2)	0.0067 (6)	0.61396 (17)	0.0493 (8)
C3	0.27837 (17)	0.2113 (6)	0.58885 (15)	0.0412 (7)
C4	0.24362 (18)	0.3937 (6)	0.53112 (15)	0.0415 (8)
C5	0.11349 (18)	0.4973 (6)	0.44218 (15)	0.0439 (8)
C6	0.1443 (2)	0.7084 (6)	0.41191 (17)	0.0520 (9)
H6	0.2013	0.7612	0.4265	0.062*
C7	0.0899 (2)	0.8403 (6)	0.35986 (17)	0.0578 (9)
H7	0.1107	0.9828	0.3396	0.069*
C8	0.0057 (2)	0.7644 (7)	0.33746 (18)	0.0640 (10)
H8	−0.0305	0.8554	0.3025	0.077*
C9	−0.0247 (2)	0.5538 (7)	0.36703 (18)	0.0614 (10)
H9	−0.0818	0.5017	0.3521	0.074*
C10	0.02861 (19)	0.4196 (6)	0.41859 (17)	0.0534 (9)
H10	0.0078	0.2755	0.4379	0.064*
C11	0.53920 (18)	0.7376 (5)	0.56816 (15)	0.0401 (7)
C12	0.56303 (17)	0.5356 (5)	0.62085 (14)	0.0375 (7)
C13	0.50074 (17)	0.3708 (6)	0.64061 (14)	0.0375 (7)
C14	0.52611 (19)	0.1898 (6)	0.69253 (15)	0.0471 (8)
H14	0.4849	0.0824	0.7067	0.057*
C15	0.6116 (2)	0.1679 (6)	0.72323 (16)	0.0514 (9)
H15	0.6280	0.0467	0.7584	0.062*
C16	0.6735 (2)	0.3229 (6)	0.70263 (16)	0.0531 (9)
H16	0.7317	0.3030	0.7225	0.064*
C17	0.64912 (18)	0.5063 (6)	0.65278 (15)	0.0462 (8)
H17	0.6911	0.6139	0.6400	0.055*

	U11	U22	U33	U12	U13	U23
N1	0.0420 (14)	0.0388 (16)	0.0482 (16)	−0.0049 (12)	0.0037 (12)	0.0094 (12)
N2	0.0447 (14)	0.0366 (16)	0.0454 (15)	−0.0032 (12)	0.0106 (12)	0.0008 (12)
N3	0.0444 (15)	0.0445 (17)	0.0609 (18)	−0.0091 (13)	0.0035 (13)	0.0065 (14)
O1	0.0483 (13)	0.0586 (16)	0.0874 (17)	−0.0120 (12)	0.0129 (12)	0.0133 (13)
O2	0.0417 (12)	0.0536 (15)	0.0688 (15)	−0.0063 (11)	0.0017 (10)	0.0184 (12)
O3	0.0425 (13)	0.0525 (15)	0.0654 (15)	−0.0061 (11)	−0.0042 (10)	0.0196 (12)
O4	0.0452 (12)	0.0473 (14)	0.0600 (14)	−0.0052 (11)	0.0054 (10)	0.0145 (11)
C1	0.080 (2)	0.052 (2)	0.062 (2)	−0.0127 (19)	0.0126 (18)	0.0109 (19)
C2	0.053 (2)	0.041 (2)	0.057 (2)	−0.0031 (17)	0.0184 (16)	−0.0053 (17)
C3	0.0392 (17)	0.0390 (19)	0.0466 (19)	−0.0019 (15)	0.0101 (14)	−0.0008 (15)
C4	0.0367 (17)	0.042 (2)	0.0473 (19)	−0.0016 (15)	0.0098 (14)	0.0003 (15)
C5	0.0417 (17)	0.046 (2)	0.0440 (18)	0.0026 (15)	0.0073 (14)	−0.0032 (16)
C6	0.0528 (19)	0.049 (2)	0.054 (2)	−0.0001 (17)	0.0078 (16)	−0.0036 (17)
C7	0.066 (2)	0.050 (2)	0.057 (2)	0.0092 (19)	0.0104 (18)	0.0040 (18)
C8	0.062 (2)	0.075 (3)	0.052 (2)	0.023 (2)	0.0026 (17)	−0.001 (2)
C9	0.0444 (19)	0.077 (3)	0.060 (2)	0.006 (2)	0.0028 (17)	−0.010 (2)
C10	0.0465 (19)	0.056 (2)	0.058 (2)	−0.0024 (17)	0.0093 (16)	−0.0066 (18)
C11	0.0435 (18)	0.0364 (19)	0.0408 (18)	−0.0064 (15)	0.0080 (14)	−0.0025 (15)
C12	0.0409 (16)	0.0365 (18)	0.0340 (16)	0.0000 (14)	0.0030 (13)	0.0001 (14)
C13	0.0386 (16)	0.0402 (19)	0.0330 (16)	0.0005 (14)	0.0030 (13)	−0.0007 (14)
C14	0.0478 (18)	0.049 (2)	0.0436 (19)	−0.0014 (16)	0.0053 (14)	0.0041 (16)
C15	0.057 (2)	0.048 (2)	0.047 (2)	0.0039 (17)	0.0000 (16)	0.0096 (17)
C16	0.0465 (19)	0.054 (2)	0.054 (2)	0.0002 (17)	−0.0056 (16)	0.0070 (18)
C17	0.0433 (17)	0.047 (2)	0.0466 (19)	−0.0033 (16)	0.0031 (14)	0.0024 (16)

N1—N2	1.310 (3)	C6—C7	1.378 (4)
N1—C13	1.395 (3)	C6—H6	0.9300
N1—H1	0.8600	C7—C8	1.373 (4)
N2—C3	1.306 (3)	C7—H7	0.9300
N3—C4	1.343 (3)	C8—C9	1.370 (5)
N3—C5	1.402 (4)	C8—H8	0.9300
N3—H3	0.8600	C9—C10	1.371 (4)
O1—C2	1.221 (3)	C9—H9	0.9300
O2—C4	1.226 (3)	C10—H10	0.9300
O3—C11	1.222 (3)	C11—C12	1.469 (4)
O4—C11	1.311 (3)	C12—C17	1.387 (4)
O4—H4	0.8200	C12—C13	1.402 (4)
C1—C2	1.498 (4)	C13—C14	1.383 (4)
C1—H1A	0.9600	C14—C15	1.369 (4)
C1—H1B	0.9600	C14—H14	0.9300
C1—H1C	0.9600	C15—C16	1.370 (4)
C2—C3	1.476 (4)	C15—H15	0.9300
C3—C4	1.491 (4)	C16—C17	1.364 (4)
C5—C6	1.381 (4)	C16—H16	0.9300
C5—C10	1.388 (4)	C17—H17	0.9300
N2—N1—C13	119.4 (2)	C6—C7—H7	119.5
N2—N1—H1	120.3	C9—C8—C7	119.5 (3)
C13—N1—H1	120.3	C9—C8—H8	120.2
C3—N2—N1	121.5 (3)	C7—C8—H8	120.2
C4—N3—C5	128.4 (3)	C8—C9—C10	120.2 (3)
C4—N3—H3	115.8	C8—C9—H9	119.9
C5—N3—H3	115.8	C10—C9—H9	119.9
C11—O4—H4	109.5	C9—C10—C5	120.5 (3)
C2—C1—H1A	109.5	C9—C10—H10	119.7
C2—C1—H1B	109.5	C5—C10—H10	119.7
H1A—C1—H1B	109.5	O3—C11—O4	121.8 (3)
C2—C1—H1C	109.5	O3—C11—C12	122.9 (3)
H1A—C1—H1C	109.5	O4—C11—C12	115.3 (2)
H1B—C1—H1C	109.5	C17—C12—C13	118.5 (3)
O1—C2—C3	121.9 (3)	C17—C12—C11	119.7 (3)
O1—C2—C1	119.4 (3)	C13—C12—C11	121.8 (2)
C3—C2—C1	118.6 (3)	C14—C13—N1	120.0 (3)
N2—C3—C2	112.8 (3)	C14—C13—C12	119.5 (3)
N2—C3—C4	123.1 (3)	N1—C13—C12	120.5 (3)
C2—C3—C4	124.1 (3)	C15—C14—C13	120.3 (3)
O2—C4—N3	123.2 (3)	C15—C14—H14	119.8
O2—C4—C3	120.1 (3)	C13—C14—H14	119.8
N3—C4—C3	116.7 (3)	C14—C15—C16	120.7 (3)
C6—C5—C10	119.2 (3)	C14—C15—H15	119.7
C6—C5—N3	124.3 (3)	C16—C15—H15	119.7
C10—C5—N3	116.6 (3)	C17—C16—C15	119.7 (3)
C7—C6—C5	119.6 (3)	C17—C16—H16	120.2
C7—C6—H6	120.2	C15—C16—H16	120.2
C5—C6—H6	120.2	C16—C17—C12	121.3 (3)
C8—C7—C6	121.0 (3)	C16—C17—H17	119.3
C8—C7—H7	119.5	C12—C17—H17	119.3
C13—N1—N2—C3	−174.3 (3)	C8—C9—C10—C5	0.9 (5)
N1—N2—C3—C2	179.2 (2)	C6—C5—C10—C9	−1.5 (5)
N1—N2—C3—C4	−1.1 (4)	N3—C5—C10—C9	178.6 (3)
O1—C2—C3—N2	−175.6 (3)	O3—C11—C12—C17	−179.3 (3)
C1—C2—C3—N2	4.2 (4)	O4—C11—C12—C17	0.9 (4)
O1—C2—C3—C4	4.7 (5)	O3—C11—C12—C13	0.2 (4)
C1—C2—C3—C4	−175.4 (3)	O4—C11—C12—C13	−179.7 (2)
C5—N3—C4—O2	−2.5 (5)	N2—N1—C13—C14	−3.6 (4)
C5—N3—C4—C3	177.4 (3)	N2—N1—C13—C12	175.1 (2)
N2—C3—C4—O2	−5.9 (4)	C17—C12—C13—C14	1.9 (4)
C2—C3—C4—O2	173.7 (3)	C11—C12—C13—C14	−177.5 (3)
N2—C3—C4—N3	174.3 (3)	C17—C12—C13—N1	−176.8 (3)
C2—C3—C4—N3	−6.1 (4)	C11—C12—C13—N1	3.7 (4)
C4—N3—C5—C6	4.3 (5)	N1—C13—C14—C15	177.3 (3)
C4—N3—C5—C10	−175.7 (3)	C12—C13—C14—C15	−1.5 (4)
C10—C5—C6—C7	1.1 (4)	C13—C14—C15—C16	−0.6 (5)
N3—C5—C6—C7	−178.9 (3)	C14—C15—C16—C17	2.2 (5)
C5—C6—C7—C8	−0.2 (5)	C15—C16—C17—C12	−1.7 (5)
C6—C7—C8—C9	−0.3 (5)	C13—C12—C17—C16	−0.3 (4)
C7—C8—C9—C10	−0.1 (5)	C11—C12—C17—C16	179.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3i	0.82	1.84	2.654 (3)	175.
N3—H3···O1	0.86	1.97	2.685 (3)	140.
N1—H1···O3	0.86	1.99	2.631 (3)	131.
N1—H1···O2	0.86	1.91	2.568 (3)	132.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3i	0.82	1.84	2.654 (3)	175
N3—H3⋯O1	0.86	1.97	2.685 (3)	140
N1—H1⋯O3	0.86	1.99	2.631 (3)	131
N1—H1⋯O2	0.86	1.91	2.568 (3)	132

Symmetry code: (i) .