2-Amino-N'-phenyl-benzohydrazide.

In the title compound, C(13)H(13)N(3)O, the NNCO unit forms dihedral angles of 35.8 (1) and 84.0 (1)° with the benzene and phenyl rings, respectively. The dihedral angles between the aromatic rings is 61.2 (1)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are linked by weak N-H⋯O hydrogen bonds into C(4) chains parallel to the c axis. Neighbouring chains are linked by weak N-H⋯N hydrogen bonds, forming R(4) (4)(20) rings, and resulting in the formation of a two-dimensional network lying parallel to (010). The packing also features π-π stacking inter-actions between phenyl rings [centroid-centroid distance = 3.803 (2) Å].

Related literature

For the pharmacological activity of quinazolinones, see: Kamal et al. (2010 ▶) and of benzotriazepinones, see: Filippakopoulos et al. (2012 ▶); Spencer et al. (2008 ▶). For the synthesis of the starting material 1H-benzo[d][1,3]oxazine-2,4-dione, see: Iwakura et al. (1976 ▶); Leiby & Heindel (1976 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H13N3O

M = 227.26

Monoclinic,

a = 6.1190 (12) Å

b = 19.921 (4) Å

c = 9.6490 (19) Å

β = 94.08 (3)°

V = 1173.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.40 × 0.21 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer

17096 measured reflections

2923 independent reflections

2330 reflections with I > 2σ(I)

R int = 0.092

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.163

S = 1.09

2923 reflections

162 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.49 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022362/ds2196sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022362/ds2196Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022362/ds2196Isup3.cml

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

C13H13N3O	F(000) = 480
Mr = 227.26	Dx = 1.287 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2923 reflections
a = 6.1190 (12) Å	θ = 3.9–28.6°
b = 19.921 (4) Å	µ = 0.09 mm−1
c = 9.6490 (19) Å	T = 293 K
β = 94.08 (3)°	Block, colourless
V = 1173.2 (4) Å3	0.40 × 0.21 × 0.10 mm
Z = 4

Nonius KappaCCD area-detector diffractometer	2330 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.092
Graphite monochromator	θmax = 28.6°, θmin = 3.9°
φ and ω scans with κ offsets	h = 0→8
17096 measured reflections	k = 0→26
2923 independent reflections	l = −12→12

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.7268P] where P = (Fo2 + 2Fc2)/3
2923 reflections	(Δ/σ)max < 0.001
162 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O1	0.6118 (2)	0.71063 (8)	0.36635 (13)	0.0430 (4)
N1	0.5506 (3)	0.73222 (8)	0.58950 (15)	0.0377 (4)
H1	0.5943	0.7527	0.6648	0.045*
N2	0.3725 (3)	0.68841 (9)	0.59083 (17)	0.0407 (4)
H2	0.2401	0.7021	0.5736	0.049*
N3	1.0637 (3)	0.73656 (12)	0.3383 (2)	0.0499 (5)
H3A	0.956 (5)	0.7108 (13)	0.312 (3)	0.059 (8)*
H3B	1.161 (5)	0.7445 (14)	0.273 (3)	0.073 (8)*
C1	0.6555 (3)	0.74322 (9)	0.47424 (17)	0.0313 (4)
C2	0.8220 (3)	0.79772 (9)	0.48509 (17)	0.0323 (4)
C3	0.7862 (3)	0.85526 (10)	0.5633 (2)	0.0421 (5)
H3	0.6585	0.8587	0.6095	0.051*
C4	0.9359 (4)	0.90690 (12)	0.5732 (3)	0.0560 (6)
H4	0.9095	0.9450	0.6253	0.067*
C5	1.1263 (4)	0.90142 (13)	0.5046 (3)	0.0575 (6)
H5	1.2291	0.9359	0.5115	0.069*
C6	1.1644 (3)	0.84588 (12)	0.4269 (2)	0.0483 (5)
H6	1.2936	0.8431	0.3820	0.058*
C7	1.0137 (3)	0.79316 (10)	0.41334 (18)	0.0364 (4)
C8	0.4207 (3)	0.62058 (11)	0.62176 (19)	0.0387 (4)
C9	0.6191 (4)	0.59962 (12)	0.6849 (2)	0.0484 (5)
H9	0.7320	0.6304	0.7030	0.058*
C10	0.6494 (5)	0.53310 (14)	0.7208 (3)	0.0668 (7)
H10	0.7826	0.5195	0.7642	0.080*
C11	0.4861 (6)	0.48666 (14)	0.6935 (3)	0.0756 (9)
H11	0.5089	0.4417	0.7165	0.091*
C12	0.2896 (6)	0.50745 (15)	0.6322 (3)	0.0744 (9)
H12	0.1780	0.4763	0.6141	0.089*
C13	0.2535 (4)	0.57384 (14)	0.5967 (2)	0.0574 (6)
H13	0.1181	0.5873	0.5562	0.069*

	U11	U22	U33	U12	U13	U23
O1	0.0418 (8)	0.0618 (9)	0.0262 (6)	−0.0055 (7)	0.0065 (5)	−0.0045 (6)
N1	0.0373 (8)	0.0497 (10)	0.0269 (7)	−0.0088 (7)	0.0078 (6)	−0.0030 (6)
N2	0.0271 (8)	0.0565 (11)	0.0392 (9)	−0.0040 (7)	0.0075 (6)	0.0005 (7)
N3	0.0307 (9)	0.0768 (14)	0.0433 (10)	0.0021 (9)	0.0102 (8)	−0.0160 (9)
C1	0.0273 (8)	0.0423 (10)	0.0244 (8)	0.0062 (7)	0.0036 (6)	0.0025 (7)
C2	0.0314 (9)	0.0411 (10)	0.0247 (8)	0.0037 (7)	0.0042 (6)	0.0069 (7)
C3	0.0428 (11)	0.0431 (11)	0.0416 (11)	0.0052 (9)	0.0110 (8)	0.0008 (8)
C4	0.0652 (15)	0.0420 (12)	0.0619 (14)	−0.0052 (11)	0.0122 (12)	−0.0036 (10)
C5	0.0571 (14)	0.0535 (14)	0.0623 (15)	−0.0169 (11)	0.0069 (11)	0.0088 (11)
C6	0.0358 (10)	0.0681 (15)	0.0418 (11)	−0.0061 (10)	0.0080 (8)	0.0098 (10)
C7	0.0312 (9)	0.0518 (11)	0.0264 (8)	0.0050 (8)	0.0029 (7)	0.0054 (7)
C8	0.0369 (10)	0.0527 (12)	0.0277 (9)	−0.0090 (9)	0.0110 (7)	−0.0053 (8)
C9	0.0466 (12)	0.0556 (13)	0.0429 (11)	−0.0047 (10)	0.0032 (9)	−0.0023 (9)
C10	0.0792 (18)	0.0638 (17)	0.0579 (15)	0.0090 (14)	0.0075 (13)	0.0107 (12)
C11	0.115 (3)	0.0522 (16)	0.0625 (17)	−0.0101 (17)	0.0263 (17)	0.0061 (12)
C12	0.094 (2)	0.0721 (19)	0.0589 (16)	−0.0427 (17)	0.0213 (15)	−0.0099 (13)
C13	0.0503 (13)	0.0728 (17)	0.0496 (13)	−0.0242 (12)	0.0069 (10)	−0.0072 (11)

O1—C1	1.240 (2)	C5—C6	1.366 (4)
N1—C1	1.341 (2)	C5—H5	0.9300
N1—N2	1.397 (2)	C6—C7	1.397 (3)
N1—H1	0.8600	C6—H6	0.9300
N2—C8	1.411 (3)	C8—C9	1.384 (3)
N2—H2	0.8600	C8—C13	1.392 (3)
N3—C7	1.386 (3)	C9—C10	1.379 (4)
N3—H3A	0.86 (3)	C9—H9	0.9300
N3—H3B	0.91 (3)	C10—C11	1.374 (4)
C1—C2	1.487 (3)	C10—H10	0.9300
C2—C3	1.398 (3)	C11—C12	1.366 (5)
C2—C7	1.407 (2)	C11—H11	0.9300
C3—C4	1.376 (3)	C12—C13	1.380 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.385 (4)	C13—H13	0.9300
C4—H4	0.9300
C1—N1—N2	121.98 (15)	C5—C6—C7	121.5 (2)
C1—N1—H1	119.0	C5—C6—H6	119.2
N2—N1—H1	119.0	C7—C6—H6	119.2
N1—N2—C8	116.67 (15)	N3—C7—C6	119.45 (18)
N1—N2—H2	121.7	N3—C7—C2	122.17 (19)
C8—N2—H2	121.7	C6—C7—C2	118.23 (18)
C7—N3—H3A	116.4 (18)	C9—C8—C13	119.1 (2)
C7—N3—H3B	113.5 (18)	C9—C8—N2	123.09 (18)
H3A—N3—H3B	115 (3)	C13—C8—N2	117.7 (2)
O1—C1—N1	121.54 (17)	C10—C9—C8	119.9 (2)
O1—C1—C2	123.18 (16)	C10—C9—H9	120.0
N1—C1—C2	115.26 (15)	C8—C9—H9	120.0
C3—C2—C7	119.10 (18)	C11—C10—C9	121.1 (3)
C3—C2—C1	120.27 (16)	C11—C10—H10	119.5
C7—C2—C1	120.60 (17)	C9—C10—H10	119.5
C4—C3—C2	121.46 (19)	C12—C11—C10	119.0 (3)
C4—C3—H3	119.3	C12—C11—H11	120.5
C2—C3—H3	119.3	C10—C11—H11	120.5
C3—C4—C5	119.1 (2)	C11—C12—C13	121.2 (3)
C3—C4—H4	120.5	C11—C12—H12	119.4
C5—C4—H4	120.5	C13—C12—H12	119.4
C6—C5—C4	120.6 (2)	C12—C13—C8	119.7 (3)
C6—C5—H5	119.7	C12—C13—H13	120.2
C4—C5—H5	119.7	C8—C13—H13	120.2
C1—N1—N2—C8	89.2 (2)	C3—C2—C7—N3	177.46 (18)
N2—N1—C1—O1	−6.4 (3)	C1—C2—C7—N3	−4.6 (3)
N2—N1—C1—C2	172.28 (16)	C3—C2—C7—C6	1.9 (3)
O1—C1—C2—C3	142.55 (19)	C1—C2—C7—C6	179.85 (16)
N1—C1—C2—C3	−36.1 (2)	N1—N2—C8—C9	17.7 (3)
O1—C1—C2—C7	−35.3 (3)	N1—N2—C8—C13	−167.37 (17)
N1—C1—C2—C7	146.01 (17)	C13—C8—C9—C10	0.6 (3)
C7—C2—C3—C4	−1.0 (3)	N2—C8—C9—C10	175.5 (2)
C1—C2—C3—C4	−178.95 (19)	C8—C9—C10—C11	0.8 (4)
C2—C3—C4—C5	−0.3 (3)	C9—C10—C11—C12	−1.3 (4)
C3—C4—C5—C6	0.7 (4)	C10—C11—C12—C13	0.4 (4)
C4—C5—C6—C7	0.3 (4)	C11—C12—C13—C8	0.9 (4)
C5—C6—C7—N3	−177.3 (2)	C9—C8—C13—C12	−1.4 (3)
C5—C6—C7—C2	−1.6 (3)	N2—C8—C13—C12	−176.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.07	2.903 (2)	162
N3—H3A···O1	0.86 (3)	2.21 (3)	2.845 (2)	131 (2)
N2—H2···N3ii	0.86	2.54	3.126 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.07	2.903 (2)	162
N3—H3A⋯O1	0.86 (3)	2.21 (3)	2.845 (2)	131 (2)
N2—H2⋯N3ii	0.86	2.54	3.126 (3)	126

Symmetry codes: (i) ; (ii) .