N′-(Adamantan-2-yl­idene)benzo­hydrazide

Almutairi, M.S.; El-Emam, A.A.; El-Brollosy, N.R.; Said-Abdelbaky, M.; García-Granda, S.

doi:10.1107/S1600536812028644

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages o2247-o2248

https://doi.org/10.1107/S1600536812028644

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N′-(Adamantan-2-ylidene)benzohydrazide

Maha S. Almutairi,^a Ali A. El-Emam,^a ‡ Nasser R. El-Brollosy,^a Mohammed Said-Abdelbaky ^b and Santiago García-Granda ^b ^*

^aCollege of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and ^bDepartamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo – CINN, C/ Julián Clavería, 8, 33006 Oviedo, Asturias, Spain
^*Correspondence e-mail: sgg@uniovi.es

(Received 21 June 2012; accepted 24 June 2012; online 30 June 2012)

The title molecule, C₁₇H₂₀N₂O, is a functionalized hydrazine with benzoyl and adamantyl substituents attached to the two hydrazine N atoms. In the crystal, molecules 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 interactions 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_r = 268.35
Orthorhombic, P b c a
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 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.139
S = 1.03
2634 reflections
185 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812028644/su2467sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812028644/su2467Isup2.hkl

checkCIF report

Comment top

Derivatives of adamantane have long been known for their diverse biological activities including antiviral activity against the influenza (Togo et al., 1968) and HIV viruses (El-Emam et al., 2004). Moreover, adamantane derivatives were reported to exhibit marked antibacterial and anti-inflammatory activities (Kadi et al., 2007, 2010; El-Emam & Ibrahim, 1991). In continuation to our interest in the chemical and pharmacological properties of adamantane derivatives (Almutairi et al., 2012; El-Emam et al., 2012), we synthesized the title compound as a precursor for potential chemotherapeutic agents. Herein, we report on the synthesis and crystal structure of the title compound.

The title molecule, Fig. 1, is a functionalized hydrazine with benzoyl and adamantyl substituents attached to the two hydrazine nitrogen atoms, N1 and N2.

In the crystal, molecules 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 interactions present within the chains (Table 1).

Related literature top

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 top

A mixture of benzohydrazide (1.36 g, 0.01 mol), 2-adamantanone (1.5 g, 0.01 mol), in ethanol (10 ml) was heated under reflux with stirring for 4 h. On cooling, the precipitated crystalline solid was filtered, dried and recrystallized from ethanol to yield 2.52 g (94%) of the title compound as colourless needle crystals [M.p. 517-519 K]. Spectroscopic data for the title compound are given in the archived CIF.

Structure description top

The title molecule, Fig. 1, is a functionalized hydrazine with benzoyl and adamantyl substituents attached to the two hydrazine nitrogen atoms, N1 and N2.

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).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2010); cell refinement: CrysAlis CCD (Oxford Diffraction, 2010); 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).

Figures top

Fig. 1. A view of the molecular structure of the title molecule with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level.

N'-(Adamantan-2-ylidene)benzohydrazide top

Crystal data top

C₁₇H₂₀N₂O	F(000) = 1152
M_r = 268.35	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0662P)²] where P = (F_o² + 2F_c²)/3
2634 reflections	(Δ/σ)_max < 0.001
185 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₇H₂₀N₂O	V = 2815.7 (2) Å³
M_r = 268.35	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 7.9698 (3) Å	µ = 0.62 mm⁻¹
b = 17.5466 (8) Å	T = 120 K
c = 20.1350 (8) Å	0.26 × 0.08 × 0.02 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2634 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	1859 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.988	R_int = 0.052
7280 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.17 e Å⁻³
2634 reflections	Δρ_min = −0.23 e Å⁻³
185 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, y, −z+1/2; (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂O
M_r	268.35
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	120
a, b, c (Å)	7.9698 (3), 17.5466 (8), 20.1350 (8)
V (Å³)	2815.7 (2)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.26 × 0.08 × 0.02

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.942, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	7280, 2634, 1859
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.139, 1.03
No. of reflections	2634
No. of parameters	185
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23

Computer programs: CrysAlis CCD (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, y, −z+1/2; (ii) −x+1, y+1/2, −z+1/2.

Footnotes

‡Additional correspondence author, e-mail: elemam5@hotmail.com.

Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, King Saud University, is greatly appreciated. Financial support from the Spanish Ministerio de Economía y Competitividad (MAT2010–15094, MAT2006–01997, Factoría de Cristalización – Consolider Ingenio 2010, and FPI grant BES-2011–046948 to MSM-A) and FEDER are gratefully acknowledged.

References

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Volume 68| Part 7| July 2012| Pages o2247-o2248

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