2-(2,3-Dimethyl-anilino)benzohydrazide.

In the title compound, C(15)H(17)N(3)O, the dihedral angle between the benzene rings is 58.05 (9)°. The non-H atoms of the hydrazide group lie in a common plane (r.m.s. deviation = 0.0006 Å) and are close to coplanar with their attached benzene ring [dihedral angle = 8.02 (9)°]. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif in the mol-ecule, and a short intra-molecular contact (H⋯H = 1.88 Å) is also observed. In the crystal, mol-ecules are linked by pairs of N-H⋯N hydrogen bonds into inversion dimers. The crystal packing also features C-H⋯π inter-actions.

Related literature

For the biological activity of fenamates, see: Boschelli et al. (1990 ▶); Reddy et al. (2010 ▶); Aboul-Fadl et al. (2011 ▶). For the synthesis, see: Reddy et al. (2010 ▶); Aboul-Fadl et al. (2011 ▶). For a related structure, see: Bhat et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H17N3O

M = 255.32

Triclinic,

a = 6.9092 (8) Å

b = 6.9609 (7) Å

c = 14.9458 (15) Å

α = 81.562 (2)°

β = 81.328 (2)°

γ = 66.269 (2)°

V = 647.56 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.28 × 0.18 × 0.13 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.977, T max = 0.989

8491 measured reflections

2218 independent reflections

1826 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.05

2218 reflections

190 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032576/hb6900sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032576/hb6900Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032576/hb6900Isup3.cml

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

C15H17N3O	Z = 2
Mr = 255.32	F(000) = 272
Triclinic, P1	Dx = 1.309 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9092 (8) Å	Cell parameters from 4059 reflections
b = 6.9609 (7) Å	θ = 2.8–30.3°
c = 14.9458 (15) Å	µ = 0.09 mm−1
α = 81.562 (2)°	T = 100 K
β = 81.328 (2)°	Block, brown
γ = 66.269 (2)°	0.28 × 0.18 × 0.13 mm
V = 647.56 (12) Å3

Bruker APEX DUO CCD diffractometer	2218 independent reflections
Radiation source: fine-focus sealed tube	1826 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.977, Tmax = 0.989	k = −8→8
8491 measured reflections	l = −17→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.042P)2 + 0.4394P] where P = (Fo2 + 2Fc2)/3
2218 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.91711 (19)	0.74672 (18)	0.09083 (8)	0.0228 (3)
N1	0.7359 (2)	0.5409 (2)	0.21691 (10)	0.0232 (4)
N2	1.2514 (3)	0.5701 (2)	0.03071 (10)	0.0228 (4)
N3	1.2742 (2)	0.7493 (2)	−0.01967 (10)	0.0220 (3)
C1	0.4439 (3)	0.4330 (3)	0.27761 (11)	0.0214 (4)
H1A	0.4763	0.3502	0.2296	0.026*
C2	0.2757 (3)	0.4418 (3)	0.34225 (12)	0.0235 (4)
H2A	0.1957	0.3636	0.3385	0.028*
C3	0.2270 (3)	0.5677 (3)	0.41256 (11)	0.0228 (4)
H3A	0.1144	0.5724	0.4562	0.027*
C4	0.3424 (3)	0.6870 (3)	0.41951 (11)	0.0202 (4)
C5	0.5160 (3)	0.6764 (3)	0.35493 (11)	0.0181 (4)
C6	0.5649 (3)	0.5483 (2)	0.28435 (11)	0.0181 (4)
C7	0.9115 (3)	0.3622 (3)	0.19813 (10)	0.0173 (4)
C8	1.0787 (3)	0.3723 (3)	0.13174 (10)	0.0173 (4)
C9	1.2500 (3)	0.1835 (3)	0.11310 (11)	0.0205 (4)
H9A	1.3578	0.1879	0.0684	0.025*
C10	1.2652 (3)	−0.0080 (3)	0.15836 (11)	0.0219 (4)
H10A	1.3814	−0.1305	0.1445	0.026*
C11	1.1052 (3)	−0.0163 (3)	0.22493 (11)	0.0211 (4)
H11A	1.1149	−0.1448	0.2565	0.025*
C12	0.9318 (3)	0.1645 (3)	0.24464 (11)	0.0196 (4)
H12A	0.8258	0.1562	0.2896	0.023*
C13	1.0721 (3)	0.5779 (3)	0.08386 (10)	0.0178 (4)
C14	0.2827 (3)	0.8260 (3)	0.49557 (12)	0.0297 (4)
H14A	0.1620	0.8139	0.5333	0.045*
H14B	0.2479	0.9698	0.4707	0.045*
H14C	0.4002	0.7831	0.5313	0.045*
C15	0.6429 (3)	0.8056 (3)	0.36060 (13)	0.0272 (4)
H15A	0.7813	0.7434	0.3285	0.041*
H15B	0.6571	0.8093	0.4232	0.041*
H15C	0.5712	0.9465	0.3338	0.041*
H1N2	1.370 (3)	0.454 (3)	0.0319 (13)	0.027 (5)*
H1N1	0.756 (3)	0.654 (3)	0.1890 (14)	0.032 (6)*
H2N3	1.204 (3)	0.867 (3)	0.0165 (13)	0.022 (5)*
H1N3	1.188 (4)	0.795 (4)	−0.0667 (17)	0.053 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0206 (7)	0.0180 (6)	0.0261 (6)	−0.0056 (5)	0.0023 (5)	−0.0010 (5)
N1	0.0212 (9)	0.0164 (8)	0.0258 (8)	−0.0049 (6)	0.0064 (6)	0.0002 (6)
N2	0.0184 (9)	0.0202 (8)	0.0263 (8)	−0.0068 (7)	0.0021 (6)	0.0018 (6)
N3	0.0226 (9)	0.0212 (8)	0.0223 (8)	−0.0101 (7)	0.0000 (6)	0.0001 (6)
C1	0.0243 (10)	0.0181 (8)	0.0220 (8)	−0.0077 (7)	−0.0084 (7)	0.0022 (7)
C2	0.0195 (10)	0.0224 (9)	0.0308 (9)	−0.0115 (8)	−0.0090 (7)	0.0073 (7)
C3	0.0121 (9)	0.0278 (10)	0.0222 (9)	−0.0048 (8)	−0.0016 (7)	0.0079 (7)
C4	0.0141 (9)	0.0215 (9)	0.0176 (8)	0.0000 (7)	−0.0042 (6)	0.0024 (6)
C5	0.0130 (9)	0.0170 (8)	0.0217 (8)	−0.0032 (7)	−0.0054 (6)	0.0019 (6)
C6	0.0151 (9)	0.0165 (8)	0.0189 (8)	−0.0039 (7)	−0.0016 (6)	0.0033 (6)
C7	0.0163 (9)	0.0191 (8)	0.0160 (8)	−0.0054 (7)	−0.0034 (6)	−0.0030 (6)
C8	0.0171 (9)	0.0208 (9)	0.0150 (8)	−0.0077 (7)	−0.0043 (6)	−0.0016 (6)
C9	0.0174 (9)	0.0230 (9)	0.0193 (8)	−0.0063 (7)	−0.0004 (7)	−0.0026 (7)
C10	0.0188 (10)	0.0197 (9)	0.0232 (9)	−0.0024 (7)	−0.0039 (7)	−0.0026 (7)
C11	0.0240 (10)	0.0195 (9)	0.0192 (8)	−0.0074 (8)	−0.0077 (7)	0.0026 (6)
C12	0.0192 (9)	0.0225 (9)	0.0172 (8)	−0.0088 (7)	−0.0016 (6)	−0.0002 (6)
C13	0.0176 (9)	0.0218 (9)	0.0155 (8)	−0.0080 (8)	−0.0031 (6)	−0.0034 (6)
C14	0.0242 (11)	0.0312 (10)	0.0246 (9)	−0.0001 (8)	−0.0051 (8)	−0.0039 (8)
C15	0.0206 (10)	0.0234 (9)	0.0385 (11)	−0.0083 (8)	−0.0042 (8)	−0.0051 (8)

O1—C13	1.236 (2)	C5—C15	1.505 (2)
N1—C7	1.372 (2)	C7—C12	1.411 (2)
N1—C6	1.422 (2)	C7—C8	1.422 (2)
N1—H1N1	0.89 (2)	C8—C9	1.401 (2)
N2—C13	1.353 (2)	C8—C13	1.489 (2)
N2—N3	1.412 (2)	C9—C10	1.375 (2)
N2—H1N2	0.89 (2)	C9—H9A	0.9300
N3—H2N3	0.963 (19)	C10—C11	1.385 (2)
N3—H1N3	0.93 (3)	C10—H10A	0.9300
C1—C2	1.382 (3)	C11—C12	1.377 (2)
C1—C6	1.394 (2)	C11—H11A	0.9300
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.383 (3)	C14—H14A	0.9600
C2—H2A	0.9300	C14—H14B	0.9600
C3—C4	1.385 (2)	C14—H14C	0.9600
C3—H3A	0.9300	C15—H15A	0.9600
C4—C5	1.406 (2)	C15—H15B	0.9600
C4—C14	1.503 (2)	C15—H15C	0.9600
C5—C6	1.395 (2)
C7—N1—C6	124.88 (14)	C9—C8—C7	118.05 (15)
C7—N1—H1N1	110.0 (14)	C9—C8—C13	121.02 (15)
C6—N1—H1N1	124.1 (13)	C7—C8—C13	120.93 (15)
C13—N2—N3	123.16 (15)	C10—C9—C8	122.59 (16)
C13—N2—H1N2	121.2 (13)	C10—C9—H9A	118.7
N3—N2—H1N2	115.0 (13)	C8—C9—H9A	118.7
N2—N3—H2N3	108.0 (11)	C9—C10—C11	119.13 (16)
N2—N3—H1N3	109.7 (15)	C9—C10—H10A	120.4
H2N3—N3—H1N3	99.5 (19)	C11—C10—H10A	120.4
C2—C1—C6	119.93 (16)	C12—C11—C10	120.42 (16)
C2—C1—H1A	120.0	C12—C11—H11A	119.8
C6—C1—H1A	120.0	C10—C11—H11A	119.8
C1—C2—C3	119.54 (16)	C11—C12—C7	121.37 (15)
C1—C2—H2A	120.2	C11—C12—H12A	119.3
C3—C2—H2A	120.2	C7—C12—H12A	119.3
C2—C3—C4	121.49 (15)	O1—C13—N2	120.69 (15)
C2—C3—H3A	119.3	O1—C13—C8	124.06 (15)
C4—C3—H3A	119.3	N2—C13—C8	115.25 (15)
C3—C4—C5	119.36 (15)	C4—C14—H14A	109.5
C3—C4—C14	120.26 (16)	C4—C14—H14B	109.5
C5—C4—C14	120.38 (16)	H14A—C14—H14B	109.5
C6—C5—C4	118.89 (15)	C4—C14—H14C	109.5
C6—C5—C15	120.69 (15)	H14A—C14—H14C	109.5
C4—C5—C15	120.39 (15)	H14B—C14—H14C	109.5
C1—C6—C5	120.76 (15)	C5—C15—H15A	109.5
C1—C6—N1	119.64 (15)	C5—C15—H15B	109.5
C5—C6—N1	119.57 (15)	H15A—C15—H15B	109.5
N1—C7—C12	120.95 (15)	C5—C15—H15C	109.5
N1—C7—C8	120.68 (15)	H15A—C15—H15C	109.5
C12—C7—C8	118.37 (15)	H15B—C15—H15C	109.5
C6—C1—C2—C3	0.9 (2)	N1—C7—C8—C9	−177.64 (15)
C1—C2—C3—C4	0.5 (3)	C12—C7—C8—C9	2.9 (2)
C2—C3—C4—C5	−1.5 (2)	N1—C7—C8—C13	2.7 (2)
C2—C3—C4—C14	178.65 (15)	C12—C7—C8—C13	−176.72 (14)
C3—C4—C5—C6	1.2 (2)	C7—C8—C9—C10	−2.1 (2)
C14—C4—C5—C6	−178.98 (15)	C13—C8—C9—C10	177.53 (15)
C3—C4—C5—C15	179.57 (16)	C8—C9—C10—C11	0.2 (3)
C14—C4—C5—C15	−0.6 (2)	C9—C10—C11—C12	0.9 (2)
C2—C1—C6—C5	−1.2 (2)	C10—C11—C12—C7	0.0 (2)
C2—C1—C6—N1	−179.12 (15)	N1—C7—C12—C11	178.61 (16)
C4—C5—C6—C1	0.1 (2)	C8—C7—C12—C11	−2.0 (2)
C15—C5—C6—C1	−178.22 (15)	N3—N2—C13—O1	−0.2 (2)
C4—C5—C6—N1	178.07 (14)	N3—N2—C13—C8	−179.91 (14)
C15—C5—C6—N1	−0.3 (2)	C9—C8—C13—O1	172.87 (15)
C7—N1—C6—C1	−61.6 (2)	C7—C8—C13—O1	−7.5 (2)
C7—N1—C6—C5	120.45 (18)	C9—C8—C13—N2	−7.4 (2)
C6—N1—C7—C12	2.0 (3)	C7—C8—C13—N2	172.23 (14)
C6—N1—C7—C8	−177.41 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N3i	0.89 (2)	2.29 (2)	3.129 (2)	158.4 (19)
N1—H1N1···O1	0.89 (2)	1.90 (2)	2.6667 (19)	143.4 (18)
C11—H11A···Cg1ii	0.93	2.58	3.303 (2)	135
C14—H14C···Cg1iii	0.96	2.77	3.535 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N3i	0.89 (2)	2.29 (2)	3.129 (2)	158.4 (19)
N1—H1N1⋯O1	0.89 (2)	1.90 (2)	2.6667 (19)	143.4 (18)
C11—H11A⋯Cg1ii	0.93	2.58	3.303 (2)	135
C14—H14C⋯Cg1iii	0.96	2.77	3.535 (2)	137

Symmetry codes: (i) ; (ii) ; (iii) .