N'-(Adamantan-2-yl-idene)benzo-hydrazide.

The title mol-ecule, C(17)H(20)N(2)O, is a functionalized hydrazine with benzoyl and adamantyl substituents attached to the two hydrazine N atoms. In the crystal, mol-ecules are linked via N-H⋯N hydrogen bonds, forming chains propagating along the a-axis direction. There are also C-H⋯O, C-H⋯N and C-H⋯π inter-actions present within the chains.

Related literature

For the biological activity of adamantane derivatives, see: Togo et al. (1968 ▶); Kadi et al. (2007 ▶, 2010 ▶); Al-Deeb et al. (2006 ▶); El-Emam et al. (2004 ▶). For the biological activity of hydrazone derivatives, see: Zheng et al. (2009 ▶); Moldovan et al. (2011 ▶). For related adamantane structures, see: Almutairi et al. (2012 ▶); Rouchal et al. (2010 ▶); El-Emam et al. (2012 ▶). For related cyclic ketone hydrazone structures, see: Sankar et al. (2010 ▶); El-Emam & Ibrahim (1991 ▶); Kia et al. (2009 ▶); Kadi et al. (2011 ▶).

Experimental

Crystal data

C17H20N2O

M = 268.35

Orthorhombic,

a = 7.9698 (3) Å

b = 17.5466 (8) Å

c = 20.1350 (8) Å

V = 2815.7 (2) Å3

Z = 8

Cu Kα radiation

μ = 0.62 mm−1

T = 120 K

0.26 × 0.08 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.942, T max = 0.988

7280 measured reflections

2634 independent reflections

1859 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.139

S = 1.03

2634 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028644/su2467sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028644/su2467Isup2.hkl

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

C17H20N2O	F(000) = 1152
Mr = 268.35	Dx = 1.266 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1578 reflections
a = 7.9698 (3) Å	θ = 3.3–70.4°
b = 17.5466 (8) Å	µ = 0.62 mm−1
c = 20.1350 (8) Å	T = 120 K
V = 2815.7 (2) Å3	Prism, colourless
Z = 8	0.26 × 0.08 × 0.02 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2634 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1859 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 10.2673 pixels mm-1	θmax = 70.4°, θmin = 3.3°
ω scans	h = −6→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −21→20
Tmin = 0.942, Tmax = 0.988	l = −24→20
7280 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0662P)2] where P = (Fo2 + 2Fc2)/3
2634 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. Spectroscopic data for the title compound:1H NMR (CDCl3, 500.13MHz): δ 1.82–1.96 (m, 14H, Adamantane-H), 7.36–7.43 (m, 3H, Ar—H), 7.51–7.53 (m, 2H, Ar—H), 8.81 (s, 1H, NH). 13C NMR (CDCl3, 125.76MHz): δ 27.70, 31.82, 36.20, 37.93, 39.06, 164.47 (Adamantane-C), 127.29, 128.66, 131.73, 133.77 (Ar—C), 171.29 (C═O).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.41632 (17)	0.06584 (9)	0.16083 (8)	0.0312 (5)
N1	0.6033 (2)	0.11608 (10)	0.23403 (9)	0.0235 (5)
N2	0.4774 (2)	0.16129 (10)	0.26108 (9)	0.0223 (5)
C1	0.5611 (2)	0.07181 (12)	0.18124 (10)	0.0246 (6)
C2	0.7017 (2)	0.02971 (12)	0.14858 (10)	0.0249 (6)
C3	0.8416 (3)	0.00356 (13)	0.18307 (12)	0.0293 (6)
C4	0.9655 (3)	−0.03725 (14)	0.14965 (14)	0.0371 (8)
C5	0.9494 (3)	−0.05134 (15)	0.08214 (14)	0.0401 (8)
C6	0.8098 (3)	−0.02579 (14)	0.04800 (12)	0.0369 (7)
C7	0.6858 (3)	0.01433 (13)	0.08093 (11)	0.0293 (6)
C8	0.5128 (2)	0.20447 (12)	0.31045 (10)	0.0220 (6)
C9	0.6735 (3)	0.21136 (13)	0.34927 (10)	0.0264 (6)
C10	0.6324 (3)	0.18818 (14)	0.42134 (11)	0.0310 (7)
C11	0.7330 (3)	0.29468 (14)	0.34814 (11)	0.0313 (7)
C12	0.4986 (3)	0.24128 (14)	0.45032 (11)	0.0296 (6)
C13	0.3753 (2)	0.25512 (12)	0.33641 (10)	0.0237 (6)
C14	0.3378 (3)	0.23380 (14)	0.40906 (11)	0.0291 (6)
C15	0.4369 (3)	0.33837 (13)	0.33421 (11)	0.0296 (7)
C16	0.5968 (3)	0.34691 (13)	0.37629 (11)	0.0288 (6)
C17	0.5592 (3)	0.32391 (14)	0.44831 (10)	0.0279 (6)
H1N	0.716 (3)	0.1276 (15)	0.2457 (12)	0.028 (6)*
H3	0.85230	0.01330	0.22830	0.0350*
H4	1.05900	−0.05500	0.17260	0.0440*
H5	1.03280	−0.07810	0.05980	0.0480*
H6	0.79920	−0.03560	0.00280	0.0440*
H7	0.59160	0.03110	0.05790	0.0350*
H9	0.75980	0.17780	0.33070	0.0320*
H10A	0.59200	0.13600	0.42220	0.0370*
H10B	0.73330	0.19080	0.44820	0.0370*
H11A	0.83450	0.29970	0.37440	0.0380*
H11B	0.75850	0.30960	0.30290	0.0380*
H12	0.47540	0.22670	0.49640	0.0360*
H13	0.27400	0.24930	0.30930	0.0280*
H14A	0.25190	0.26730	0.42680	0.0350*
H14B	0.29650	0.18190	0.41130	0.0350*
H15A	0.46020	0.35290	0.28870	0.0360*
H15B	0.35010	0.37190	0.35130	0.0360*
H16	0.63530	0.39990	0.37500	0.0350*
H17A	0.65970	0.32930	0.47510	0.0330*
H17B	0.47350	0.35710	0.46660	0.0330*

	U11	U22	U33	U12	U13	U23
O1	0.0275 (7)	0.0321 (9)	0.0339 (8)	0.0024 (7)	−0.0040 (6)	−0.0082 (7)
N1	0.0219 (8)	0.0216 (9)	0.0270 (9)	0.0025 (7)	0.0013 (7)	−0.0049 (8)
N2	0.0230 (8)	0.0205 (9)	0.0235 (8)	0.0016 (7)	0.0015 (7)	−0.0002 (7)
C1	0.0276 (10)	0.0218 (11)	0.0244 (10)	0.0000 (9)	0.0005 (8)	0.0009 (9)
C2	0.0280 (10)	0.0190 (10)	0.0277 (11)	−0.0026 (8)	0.0062 (9)	−0.0018 (9)
C3	0.0274 (10)	0.0225 (11)	0.0381 (12)	−0.0009 (9)	0.0020 (9)	−0.0011 (10)
C4	0.0292 (11)	0.0298 (13)	0.0522 (15)	0.0041 (10)	0.0051 (10)	−0.0029 (12)
C5	0.0431 (13)	0.0270 (12)	0.0501 (15)	0.0032 (10)	0.0223 (12)	−0.0052 (12)
C6	0.0528 (14)	0.0248 (12)	0.0330 (12)	−0.0033 (11)	0.0161 (12)	−0.0025 (10)
C7	0.0374 (11)	0.0214 (11)	0.0290 (11)	−0.0013 (9)	0.0022 (9)	−0.0010 (9)
C8	0.0242 (9)	0.0199 (10)	0.0220 (10)	−0.0005 (8)	−0.0001 (8)	0.0015 (9)
C9	0.0245 (9)	0.0289 (12)	0.0259 (10)	0.0035 (9)	−0.0012 (9)	−0.0065 (9)
C10	0.0388 (11)	0.0284 (13)	0.0257 (11)	0.0050 (10)	−0.0087 (10)	−0.0007 (10)
C11	0.0299 (10)	0.0342 (13)	0.0298 (11)	−0.0096 (10)	0.0010 (9)	−0.0049 (10)
C12	0.0380 (11)	0.0288 (12)	0.0220 (10)	0.0016 (10)	0.0010 (9)	0.0008 (9)
C13	0.0250 (9)	0.0219 (11)	0.0242 (10)	0.0016 (8)	0.0003 (8)	−0.0014 (9)
C14	0.0307 (10)	0.0270 (12)	0.0296 (11)	−0.0017 (9)	0.0070 (9)	−0.0039 (10)
C15	0.0371 (11)	0.0235 (12)	0.0282 (11)	0.0032 (9)	−0.0021 (9)	0.0002 (9)
C16	0.0359 (11)	0.0222 (11)	0.0284 (11)	−0.0055 (10)	−0.0006 (9)	−0.0017 (9)
C17	0.0313 (10)	0.0276 (12)	0.0248 (10)	0.0014 (9)	−0.0031 (9)	−0.0060 (9)

O1—C1	1.229 (2)	C15—C16	1.538 (3)
N1—N2	1.390 (2)	C16—C17	1.535 (3)
N1—C1	1.359 (3)	C3—H3	0.9300
N2—C8	1.281 (3)	C4—H4	0.9300
N1—H1N	0.95 (2)	C5—H5	0.9300
C1—C2	1.495 (3)	C6—H6	0.9300
C2—C7	1.394 (3)	C7—H7	0.9300
C2—C3	1.391 (3)	C9—H9	0.9800
C3—C4	1.393 (3)	C10—H10A	0.9700
C4—C5	1.388 (4)	C10—H10B	0.9700
C5—C6	1.383 (3)	C11—H11A	0.9700
C6—C7	1.383 (3)	C11—H11B	0.9700
C8—C9	1.505 (3)	C12—H12	0.9800
C8—C13	1.505 (3)	C13—H13	0.9800
C9—C11	1.537 (3)	C14—H14A	0.9700
C9—C10	1.542 (3)	C14—H14B	0.9700
C10—C12	1.532 (3)	C15—H15A	0.9700
C11—C16	1.530 (3)	C15—H15B	0.9700
C12—C17	1.529 (3)	C16—H16	0.9800
C12—C14	1.533 (3)	C17—H17A	0.9700
C13—C14	1.539 (3)	C17—H17B	0.9700
C13—C15	1.542 (3)
N2—N1—C1	117.00 (15)	C5—C6—H6	120.00
N1—N2—C8	118.84 (16)	C7—C6—H6	120.00
N2—N1—H1N	117.7 (15)	C2—C7—H7	120.00
C1—N1—H1N	123.3 (15)	C6—C7—H7	120.00
N1—C1—C2	116.18 (15)	C8—C9—H9	111.00
O1—C1—C2	120.97 (18)	C10—C9—H9	110.00
O1—C1—N1	122.86 (18)	C11—C9—H9	110.00
C1—C2—C7	117.22 (17)	C9—C10—H10A	110.00
C3—C2—C7	119.77 (19)	C9—C10—H10B	110.00
C1—C2—C3	122.97 (19)	C12—C10—H10A	110.00
C2—C3—C4	119.8 (2)	C12—C10—H10B	110.00
C3—C4—C5	120.0 (2)	H10A—C10—H10B	108.00
C4—C5—C6	120.3 (2)	C9—C11—H11A	110.00
C5—C6—C7	120.1 (2)	C9—C11—H11B	110.00
C2—C7—C6	120.1 (2)	C16—C11—H11A	110.00
N2—C8—C13	117.29 (16)	C16—C11—H11B	110.00
N2—C8—C9	129.62 (18)	H11A—C11—H11B	108.00
C9—C8—C13	113.07 (17)	C10—C12—H12	109.00
C8—C9—C11	109.34 (18)	C14—C12—H12	109.00
C8—C9—C10	106.66 (18)	C17—C12—H12	109.00
C10—C9—C11	109.29 (18)	C8—C13—H13	110.00
C9—C10—C12	110.24 (19)	C14—C13—H13	110.00
C9—C11—C16	110.21 (19)	C15—C13—H13	110.00
C10—C12—C17	110.30 (19)	C12—C14—H14A	110.00
C10—C12—C14	108.88 (19)	C12—C14—H14B	110.00
C14—C12—C17	109.33 (19)	C13—C14—H14A	110.00
C8—C13—C15	108.53 (15)	C13—C14—H14B	110.00
C8—C13—C14	109.15 (17)	H14A—C14—H14B	108.00
C14—C13—C15	108.63 (17)	C13—C15—H15A	110.00
C12—C14—C13	109.39 (18)	C13—C15—H15B	110.00
C13—C15—C16	109.90 (18)	C16—C15—H15A	110.00
C11—C16—C15	109.00 (18)	C16—C15—H15B	110.00
C11—C16—C17	109.34 (19)	H15A—C15—H15B	108.00
C15—C16—C17	109.46 (19)	C11—C16—H16	110.00
C12—C17—C16	109.64 (18)	C15—C16—H16	110.00
C2—C3—H3	120.00	C17—C16—H16	110.00
C4—C3—H3	120.00	C12—C17—H17A	110.00
C3—C4—H4	120.00	C12—C17—H17B	110.00
C5—C4—H4	120.00	C16—C17—H17A	110.00
C4—C5—H5	120.00	C16—C17—H17B	110.00
C6—C5—H5	120.00	H17A—C17—H17B	108.00
C1—N1—N2—C8	−179.23 (19)	C9—C8—C13—C14	−59.8 (2)
N2—N1—C1—O1	−6.1 (3)	C9—C8—C13—C15	58.4 (2)
N2—N1—C1—C2	174.01 (17)	C8—C9—C10—C12	−60.3 (2)
N1—N2—C8—C9	−4.7 (3)	C11—C9—C10—C12	57.8 (2)
N1—N2—C8—C13	177.34 (17)	C8—C9—C11—C16	57.4 (2)
O1—C1—C2—C3	−148.1 (2)	C10—C9—C11—C16	−59.1 (2)
O1—C1—C2—C7	29.5 (3)	C9—C10—C12—C14	61.6 (2)
N1—C1—C2—C3	31.7 (3)	C9—C10—C12—C17	−58.3 (2)
N1—C1—C2—C7	−150.6 (2)	C9—C11—C16—C15	−59.3 (2)
C1—C2—C3—C4	178.1 (2)	C9—C11—C16—C17	60.3 (2)
C7—C2—C3—C4	0.5 (3)	C10—C12—C14—C13	−59.2 (2)
C1—C2—C7—C6	−178.7 (2)	C17—C12—C14—C13	61.3 (2)
C3—C2—C7—C6	−1.0 (3)	C10—C12—C17—C16	59.2 (2)
C2—C3—C4—C5	0.3 (4)	C14—C12—C17—C16	−60.5 (2)
C3—C4—C5—C6	−0.8 (4)	C8—C13—C14—C12	57.5 (2)
C4—C5—C6—C7	0.3 (4)	C15—C13—C14—C12	−60.7 (2)
C5—C6—C7—C2	0.5 (4)	C8—C13—C15—C16	−58.7 (2)
N2—C8—C9—C10	−117.8 (2)	C14—C13—C15—C16	59.8 (2)
N2—C8—C9—C11	124.1 (2)	C13—C15—C16—C11	60.2 (2)
C13—C8—C9—C10	60.2 (2)	C13—C15—C16—C17	−59.4 (2)
C13—C8—C9—C11	−57.9 (2)	C11—C16—C17—C12	−59.9 (2)
N2—C8—C13—C14	118.5 (2)	C15—C16—C17—C12	59.4 (2)
N2—C8—C13—C15	−123.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2i	0.95 (2)	2.17 (2)	3.087 (2)	162 (2)
C3—H3···O1i	0.93	2.47	3.381 (3)	167
C9—H9···O1i	0.98	2.33	3.210 (3)	149
C9—H9···N2i	0.98	2.55	3.402 (3)	145
C15—H15A···Cg1ii	0.97	2.57	3.519 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2i	0.95 (2)	2.17 (2)	3.087 (2)	162 (2)
C3—H3⋯O1i	0.93	2.47	3.381 (3)	167
C9—H9⋯O1i	0.98	2.33	3.210 (3)	149
C9—H9⋯N2i	0.98	2.55	3.402 (3)	145
C15—H15A⋯Cg1ii	0.97	2.57	3.519 (3)	164

Symmetry codes: (i) ; (ii) .