Crystal structure of 1-isopropyl-4,7-dimethyl-3-nitro-naphthalene.

The title compound, C15H17NO2, was synthesized from a mixture of α-himachalene (2-methyl-ene-6,6,9-tri-methylbi-cyclo-[5.4.0(1,7)]undec-8-ene) and β-himachalene (2,6,6,9-tetra-methylbi-cyclo-[5.4.0(1,7)]undeca-1,8-diene), which were isolated from an oil of the Atlas cedar (Cedrus Atlantica). The naphthalene ring system makes dihedral angles of 68.6 (2) and 44.3 (2)°, respectively, with its attached isopropyl C/C/C plane and the nitro group. In the crystal, mol-ecules held together by a C-H⋯O inter-action, forming a chain along [-101].

Related literature

For the main constituents of the essential oil of the Atlas cedar, see: El Haib et al. (2011 ▸); Loubidi et al. (2014 ▸). For the reactivity of these sesquiterpenes and their derivatives, see: Oukhrib et al. (2013 ▸); Zaki et al. (2014 ▸); Benharref et al. (2015 ▸). For anti­fungal activity of these sesquiterpenes and derivatives, see: Daoubi et al. (2004 ▸).

Experimental

Crystal data

C15H17NO2

M = 243.30

Monoclinic,

a = 9.7637 (7) Å

b = 12.6508 (9) Å

c = 11.6162 (8) Å

β = 113.897 (2)°

V = 1311.82 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.45 × 0.35 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.652, T max = 0.746

21437 measured reflections

2686 independent reflections

2164 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.147

S = 1.07

2686 reflections

167 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015014395/is5409sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014395/is5409Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015014395/is5409Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015014395/is5409fig1.tif

Mol­ecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

Click here for additional data file.

ac . DOI: 10.1107/S2056989015014395/is5409fig2.tif

Partial packing view showing the C—H⋯O inter­actions (dashed lines) and the formation of a chain along the ac diagonal.

CCDC reference: 1415866

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H17NO2	F(000) = 520
Mr = 243.30	Dx = 1.232 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.7637 (7) Å	Cell parameters from 2686 reflections
b = 12.6508 (9) Å	θ = 2.3–26.4°
c = 11.6162 (8) Å	µ = 0.08 mm−1
β = 113.897 (2)°	T = 296 K
V = 1311.82 (16) Å3	Box, colourless
Z = 4	0.45 × 0.35 × 0.30 mm

Bruker APEXII CCD diffractometer	2686 independent reflections
Radiation source: fine-focus sealed tube	2164 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→12
Tmin = 0.652, Tmax = 0.746	k = −15→15
21437 measured reflections	l = −14→12

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0738P)2 + 0.3258P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2686 reflections	Δρmax = 0.22 e Å−3
167 parameters	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.

	x	y	z	Uiso*/Ueq
C1	0.48931 (16)	0.74540 (11)	0.55728 (13)	0.0410 (3)
C2	0.53127 (17)	0.79068 (11)	0.46989 (14)	0.0458 (4)
H2	0.4856	0.8530	0.4305	0.055*
C3	0.64274 (16)	0.74433 (12)	0.43844 (13)	0.0434 (3)
C4	0.71449 (15)	0.65180 (12)	0.48818 (13)	0.0426 (3)
C5	0.66896 (14)	0.60094 (11)	0.57753 (12)	0.0391 (3)
C6	0.73317 (18)	0.50374 (13)	0.63462 (15)	0.0506 (4)
H6	0.8081	0.4735	0.6153	0.061*
C7	0.68819 (19)	0.45344 (13)	0.71690 (15)	0.0540 (4)
H7	0.7323	0.3894	0.7520	0.065*
C8	0.57617 (17)	0.49648 (12)	0.74988 (13)	0.0464 (4)
C9	0.51403 (16)	0.59105 (12)	0.69828 (13)	0.0428 (3)
H9	0.4410	0.6204	0.7208	0.051*
C10	0.55666 (14)	0.64644 (11)	0.61141 (12)	0.0370 (3)
C11	0.37186 (18)	0.79765 (12)	0.59387 (16)	0.0509 (4)
H11	0.3962	0.7793	0.6820	0.061*
C12	0.2168 (2)	0.75490 (16)	0.5164 (2)	0.0741 (6)
H12A	0.1910	0.7690	0.4289	0.111*
H12B	0.1455	0.7886	0.5420	0.111*
H12C	0.2155	0.6800	0.5293	0.111*
C13	0.3728 (2)	0.91812 (14)	0.5855 (2)	0.0693 (5)
H13A	0.4727	0.9438	0.6317	0.104*
H13B	0.3074	0.9472	0.6207	0.104*
H13C	0.3388	0.9391	0.4989	0.104*
C14	0.82959 (18)	0.60027 (15)	0.45058 (17)	0.0592 (4)
H14A	0.8302	0.6348	0.3772	0.089*
H14B	0.8050	0.5270	0.4322	0.089*
H14C	0.9268	0.6062	0.5184	0.089*
C15	0.5277 (2)	0.43966 (15)	0.84114 (16)	0.0637 (5)
H15A	0.5986	0.4530	0.9257	0.096*
H15B	0.5228	0.3651	0.8247	0.096*
H15C	0.4307	0.4647	0.8312	0.096*
N1	0.67771 (18)	0.80420 (11)	0.34458 (13)	0.0576 (4)
O1	0.5730 (2)	0.84079 (13)	0.25427 (14)	0.0865 (5)
O2	0.80848 (18)	0.81719 (14)	0.36267 (14)	0.0869 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0427 (7)	0.0414 (7)	0.0442 (7)	0.0013 (6)	0.0230 (6)	−0.0011 (6)
C2	0.0545 (8)	0.0401 (7)	0.0483 (8)	0.0027 (6)	0.0265 (7)	0.0034 (6)
C3	0.0503 (8)	0.0463 (8)	0.0409 (7)	−0.0084 (6)	0.0261 (6)	−0.0040 (6)
C4	0.0370 (7)	0.0527 (8)	0.0422 (7)	−0.0046 (6)	0.0204 (6)	−0.0091 (6)
C5	0.0344 (7)	0.0462 (8)	0.0368 (7)	0.0005 (5)	0.0145 (5)	−0.0035 (6)
C6	0.0465 (8)	0.0531 (9)	0.0529 (8)	0.0121 (6)	0.0209 (7)	0.0009 (7)
C7	0.0576 (9)	0.0491 (8)	0.0495 (8)	0.0092 (7)	0.0157 (7)	0.0083 (7)
C8	0.0489 (8)	0.0496 (8)	0.0381 (7)	−0.0055 (6)	0.0149 (6)	0.0019 (6)
C9	0.0432 (7)	0.0497 (8)	0.0403 (7)	−0.0003 (6)	0.0219 (6)	−0.0007 (6)
C10	0.0362 (6)	0.0408 (7)	0.0361 (7)	−0.0010 (5)	0.0167 (5)	−0.0027 (5)
C11	0.0559 (9)	0.0490 (9)	0.0586 (9)	0.0116 (7)	0.0344 (7)	0.0050 (7)
C12	0.0555 (10)	0.0673 (12)	0.1121 (16)	0.0006 (9)	0.0469 (11)	−0.0110 (11)
C13	0.0697 (11)	0.0513 (10)	0.0976 (14)	0.0112 (8)	0.0450 (11)	−0.0053 (9)
C14	0.0516 (9)	0.0752 (11)	0.0628 (10)	0.0041 (8)	0.0357 (8)	−0.0067 (8)
C15	0.0735 (11)	0.0662 (11)	0.0514 (9)	−0.0090 (9)	0.0253 (8)	0.0127 (8)
N1	0.0814 (10)	0.0541 (8)	0.0539 (8)	−0.0129 (7)	0.0444 (8)	−0.0072 (6)
O1	0.1158 (12)	0.0876 (10)	0.0662 (9)	0.0121 (9)	0.0474 (9)	0.0262 (8)
O2	0.0923 (10)	0.1066 (12)	0.0894 (10)	−0.0334 (9)	0.0653 (9)	−0.0057 (8)

C1—C2	1.3651 (19)	C9—H9	0.9300
C1—C10	1.4353 (19)	C11—C12	1.514 (3)
C1—C11	1.5256 (19)	C11—C13	1.527 (2)
C2—C3	1.408 (2)	C11—H11	0.9800
C2—H2	0.9300	C12—H12A	0.9600
C3—C4	1.366 (2)	C12—H12B	0.9600
C3—N1	1.4767 (18)	C12—H12C	0.9600
C4—C5	1.4362 (19)	C13—H13A	0.9600
C4—C14	1.5087 (19)	C13—H13B	0.9600
C5—C6	1.417 (2)	C13—H13C	0.9600
C5—C10	1.4276 (18)	C14—H14A	0.9600
C6—C7	1.361 (2)	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—C8	1.407 (2)	C15—H15A	0.9600
C7—H7	0.9300	C15—H15B	0.9600
C8—C9	1.365 (2)	C15—H15C	0.9600
C8—C15	1.507 (2)	N1—O2	1.218 (2)
C9—C10	1.4223 (18)	N1—O1	1.221 (2)
C2—C1—C10	118.00 (12)	C1—C11—C13	112.97 (14)
C2—C1—C11	120.75 (13)	C12—C11—H11	107.3
C10—C1—C11	121.24 (12)	C1—C11—H11	107.3
C1—C2—C3	120.96 (13)	C13—C11—H11	107.3
C1—C2—H2	119.5	C11—C12—H12A	109.5
C3—C2—H2	119.5	C11—C12—H12B	109.5
C4—C3—C2	124.38 (13)	H12A—C12—H12B	109.5
C4—C3—N1	121.29 (13)	C11—C12—H12C	109.5
C2—C3—N1	114.33 (13)	H12A—C12—H12C	109.5
C3—C4—C5	115.69 (12)	H12B—C12—H12C	109.5
C3—C4—C14	124.21 (13)	C11—C13—H13A	109.5
C5—C4—C14	120.04 (14)	C11—C13—H13B	109.5
C6—C5—C10	117.68 (12)	H13A—C13—H13B	109.5
C6—C5—C4	121.27 (12)	C11—C13—H13C	109.5
C10—C5—C4	121.05 (13)	H13A—C13—H13C	109.5
C7—C6—C5	121.81 (14)	H13B—C13—H13C	109.5
C7—C6—H6	119.1	C4—C14—H14A	109.5
C5—C6—H6	119.1	C4—C14—H14B	109.5
C6—C7—C8	121.20 (14)	H14A—C14—H14B	109.5
C6—C7—H7	119.4	C4—C14—H14C	109.5
C8—C7—H7	119.4	H14A—C14—H14C	109.5
C9—C8—C7	118.42 (13)	H14B—C14—H14C	109.5
C9—C8—C15	121.09 (15)	C8—C15—H15A	109.5
C7—C8—C15	120.49 (15)	C8—C15—H15B	109.5
C8—C9—C10	122.51 (13)	H15A—C15—H15B	109.5
C8—C9—H9	118.7	C8—C15—H15C	109.5
C10—C9—H9	118.7	H15A—C15—H15C	109.5
C9—C10—C5	118.37 (12)	H15B—C15—H15C	109.5
C9—C10—C1	121.79 (12)	O2—N1—O1	123.46 (15)
C5—C10—C1	119.85 (12)	O2—N1—C3	118.79 (15)
C12—C11—C1	111.31 (13)	O1—N1—C3	117.71 (15)
C12—C11—C13	110.42 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2i	0.93	2.60	3.4823 (18)	159

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C9H9O2i	0.93	2.60	3.4823(18)	159

Symmetry code: (i) .