1,6-Bis(prop-2-yn-1-yl­­oxy)naphthalene

The title compound, C₁₆H₁₂O₂, contains two prop-2-yn-1-yl­oxy groups attached to a naphthalene ring system at the 1- and 6-positions. The crystal packing includes an inter­molecular C—H⋯π inter­action between a terminal ethynyl H atom and an ethynyl group on a glide-related mol­ecule and another inter­action between an O-atom-linked methyl­ene H and an ethynyl group of a different glide-related mol­ecule.

Related literature

For the preparation of the title compound, see: Srinivasan et al. (2006). For biological and commercial applications of naphthalene derivatives, see Morikawa & Takahashi (2004).

Experimental

Crystal data

• C₁₆H₁₂O₂

• M_r = 236.26

• Monoclinic, P 2₁ /c

• a = 5.1472 (9) Å

• b = 10.3788 (19) Å

• c = 23.409 (4) Å

• β = 95.459 (3)°

• V = 1244.9 (4) ų

• Z = 4

• Mo Kα radiation

• μ = 0.08 mm⁻¹

• T = 298 K

• 0.16 × 0.12 × 0.10 mm

Data collection

• Bruker SMART CCD area-detector diffractometer

• 7491 measured reflections

• 2306 independent reflections

• 1636 reflections with I > 2σ(I)

• R_int = 0.118

Refinement

• R[F² > 2σ(F²)] = 0.051

• wR(F²) = 0.133

• S = 1.02

• 2306 reflections

• 163 parameters

• H-atom parameters constrained

• Δρ_max = 0.15 e Å⁻³

• Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C4/C9/C10 and C4–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯Cg1^i	0.97	2.75	3.602 (2)	147
C14—H14A⋯Cg2^ii	0.97	2.76	3.457 (2)	130
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

S1. Comment

Naphthalene derivatives have been extensively employed in many fields, and some possess important biological and commercial applications, including use as disinfectants, insecticides and auxin plant hormones, rooting agents and so on (Morikawa & Takahashi, 2004;). The title compound was prepared by a rapid reaction between hydroxybenzene and prop-2-yn-1-yl-4-methylbenzenesulfonate with the introduction of sodium hydride (Srinivasan et al., 2006). Here we report the crystal structure of the title compound (Fig. 1). X-ray analysis reveals that the crystal structure is stabilized by intermolecular non-classical C—H···π interactions.

Related literature

For the preparation of the title compound, see: Srinivasan et al. (2006). For biological and commercial applications of naphthalene derivatives, see Morikawa & Takahashi (2004).

S2. Experimental

The title compound was synthesized according to the literature procedure of Srinivasan et al. (2006). Single crystals suitable for x-ray diffraction were prepared by slow evaporation of a solution of the title compound in petroleum ether: ethyl acetate (75: 1) at room temperature.

S3. Refinement

All H atoms were initially located in a difference map, but were constrained to idealized geometry. Constrained bond lengths and isotropic displacement parameters: (C—H = 0.97 Å) and U_iso(H) = 1.2 U_eq(C) for methylene, and (C—H = 0.93 Å) and U_iso(H) = 1.2U_eq(C) for aromatic H atoms, and (C—H = 0.93 Å) and U_iso(H) = 1.2U_eq(C) for alkynyl H atoms

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

Fig. 1. A view of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented by spheres of arbitrary radius.

1,6-Bis(prop-2-yn-1-yloxy)naphthalene

Crystal data

C16H12O2	F(000) = 496
Mr = 236.26	Dx = 1.261 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1759 reflections
a = 5.1472 (9) Å	θ = 2.6–24.9°
b = 10.3788 (19) Å	µ = 0.08 mm^−1
c = 23.409 (4) Å	T = 298 K
β = 95.459 (3)°	Block, colorless
V = 1244.9 (4) Å^3	0.16 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1636 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.118
Graphite monochromator	θmax = 25.5°, θmin = 2.2°
ϕ and ω scans	h = −6→6
7491 measured reflections	k = −12→12
2306 independent reflections	l = −27→28

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0446P)^2] where P = (Fo^2 + 2Fc^2)/3
2306 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6519 (3)	0.40676 (17)	0.23456 (7)	0.0423 (4)
C2	0.8336 (3)	0.30562 (16)	0.23889 (8)	0.0466 (5)
H2	0.8254	0.2419	0.2108	0.056*
C3	1.0218 (3)	0.29989 (16)	0.28383 (8)	0.0449 (5)
H3	1.1412	0.2324	0.2859	0.054*
C4	1.0385 (3)	0.39506 (15)	0.32738 (7)	0.0398 (4)
C5	1.2313 (4)	0.39288 (17)	0.37514 (8)	0.0457 (5)
C6	1.2356 (4)	0.48592 (18)	0.41649 (8)	0.0548 (5)
H6	1.3595	0.4829	0.4481	0.066*
C7	1.0524 (4)	0.58592 (19)	0.41099 (8)	0.0605 (6)
H7	1.0583	0.6494	0.4391	0.073*
C8	0.8668 (4)	0.59320 (18)	0.36603 (8)	0.0532 (5)
H8	0.7474	0.6607	0.3635	0.064*
C9	0.8560 (3)	0.49704 (16)	0.32270 (7)	0.0420 (5)
C10	0.6626 (3)	0.50095 (16)	0.27556 (7)	0.0442 (5)
H10	0.5421	0.5680	0.2724	0.053*
C11	0.2933 (4)	0.50677 (18)	0.18126 (8)	0.0514 (5)
H11A	0.3888	0.5864	0.1775	0.062*
H11B	0.1976	0.5134	0.2149	0.062*
C12	0.1124 (4)	0.48650 (19)	0.13036 (9)	0.0582 (6)
C13	−0.0400 (5)	0.4787 (2)	0.09085 (10)	0.0813 (8)
H13	−0.1625	0.4725	0.0591	0.098*
C14	1.6025 (4)	0.2831 (2)	0.42217 (8)	0.0543 (5)
H14A	1.6820	0.3672	0.4288	0.065*
H14B	1.7370	0.2243	0.4119	0.065*
C15	1.5032 (4)	0.23846 (19)	0.47507 (9)	0.0558 (5)
C16	1.4286 (5)	0.2017 (2)	0.51684 (11)	0.0820 (8)
H16	1.3683	0.1719	0.5506	0.098*
O1	0.4707 (2)	0.40117 (12)	0.18760 (5)	0.0510 (4)
O2	1.4033 (2)	0.29188 (12)	0.37524 (5)	0.0534 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0397 (10)	0.0445 (10)	0.0427 (10)	−0.0044 (8)	0.0047 (8)	0.0026 (8)
C2	0.0490 (11)	0.0427 (11)	0.0486 (11)	−0.0011 (9)	0.0073 (9)	−0.0047 (8)
C3	0.0458 (11)	0.0389 (10)	0.0514 (11)	0.0049 (8)	0.0111 (9)	−0.0004 (8)
C4	0.0421 (10)	0.0377 (10)	0.0409 (10)	−0.0034 (8)	0.0102 (8)	0.0036 (8)
C5	0.0453 (10)	0.0441 (10)	0.0480 (11)	0.0010 (9)	0.0069 (9)	0.0027 (9)
C6	0.0553 (12)	0.0552 (12)	0.0517 (12)	0.0022 (10)	−0.0063 (9)	−0.0077 (9)
C7	0.0661 (13)	0.0500 (12)	0.0637 (13)	0.0027 (10)	−0.0027 (11)	−0.0177 (10)
C8	0.0582 (12)	0.0405 (11)	0.0601 (13)	0.0047 (9)	0.0025 (11)	−0.0049 (9)
C9	0.0440 (11)	0.0375 (10)	0.0452 (10)	−0.0030 (8)	0.0078 (8)	0.0014 (8)
C10	0.0438 (11)	0.0374 (10)	0.0519 (11)	0.0037 (8)	0.0070 (9)	0.0021 (8)
C11	0.0525 (12)	0.0435 (11)	0.0570 (12)	−0.0012 (9)	−0.0004 (10)	0.0032 (9)
C12	0.0550 (13)	0.0540 (13)	0.0639 (14)	−0.0013 (10)	−0.0029 (11)	0.0030 (10)
C13	0.0733 (16)	0.0845 (18)	0.0803 (17)	−0.0014 (13)	−0.0239 (14)	−0.0015 (13)
C14	0.0470 (11)	0.0582 (12)	0.0562 (12)	0.0077 (9)	−0.0033 (10)	0.0021 (9)
C15	0.0614 (13)	0.0526 (12)	0.0521 (13)	0.0025 (10)	−0.0008 (10)	0.0029 (10)
C16	0.0972 (19)	0.0841 (18)	0.0662 (16)	0.0053 (15)	0.0150 (14)	0.0144 (13)
O1	0.0486 (7)	0.0505 (8)	0.0524 (8)	0.0020 (6)	−0.0027 (6)	−0.0058 (6)
O2	0.0547 (8)	0.0556 (8)	0.0485 (8)	0.0138 (6)	−0.0022 (6)	−0.0024 (6)

Geometric parameters (Å, º)

C1—C10	1.368 (2)	C8—H8	0.9300
C1—O1	1.3732 (19)	C9—C10	1.415 (2)
C1—C2	1.403 (2)	C10—H10	0.9300
C2—C3	1.362 (2)	C11—O1	1.425 (2)
C2—H2	0.9300	C11—C12	1.456 (3)
C3—C4	1.416 (2)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C9	1.413 (2)	C12—C13	1.157 (3)
C4—C5	1.423 (2)	C13—H13	0.9300
C5—C6	1.366 (2)	C14—O2	1.433 (2)
C5—O2	1.372 (2)	C14—C15	1.459 (3)
C6—C7	1.400 (3)	C14—H14A	0.9700
C6—H6	0.9300	C14—H14B	0.9700
C7—C8	1.354 (2)	C15—C16	1.149 (3)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.420 (2)
C10—C1—O1	124.83 (16)	C4—C9—C10	119.71 (15)
C10—C1—C2	120.12 (17)	C4—C9—C8	119.37 (17)
O1—C1—C2	115.05 (15)	C10—C9—C8	120.91 (16)
C3—C2—C1	120.58 (16)	C1—C10—C9	120.37 (16)
C3—C2—H2	119.7	C1—C10—H10	119.8
C1—C2—H2	119.7	C9—C10—H10	119.8
C2—C3—C4	121.04 (16)	O1—C11—C12	109.13 (15)
C2—C3—H3	119.5	O1—C11—H11A	109.9
C4—C3—H3	119.5	C12—C11—H11A	109.9
C9—C4—C3	118.18 (16)	O1—C11—H11B	109.9
C9—C4—C5	118.81 (16)	C12—C11—H11B	109.9
C3—C4—C5	123.01 (16)	H11A—C11—H11B	108.3
C6—C5—O2	124.88 (17)	C13—C12—C11	175.0 (2)
C6—C5—C4	120.59 (17)	C12—C13—H13	180.0
O2—C5—C4	114.53 (15)	O2—C14—C15	112.83 (15)
C5—C6—C7	119.56 (18)	O2—C14—H14A	109.0
C5—C6—H6	120.2	C15—C14—H14A	109.0
C7—C6—H6	120.2	O2—C14—H14B	109.0
C8—C7—C6	122.14 (18)	C15—C14—H14B	109.0
C8—C7—H7	118.9	H14A—C14—H14B	107.8
C6—C7—H7	118.9	C16—C15—C14	178.7 (2)
C7—C8—C9	119.51 (18)	C15—C16—H16	180.0
C7—C8—H8	120.2	C1—O1—C11	115.49 (13)
C9—C8—H8	120.2	C5—O2—C14	117.69 (14)
C10—C1—C2—C3	0.1 (3)	C3—C4—C9—C8	179.46 (16)
O1—C1—C2—C3	−179.48 (14)	C5—C4—C9—C8	−1.0 (2)
C1—C2—C3—C4	0.3 (3)	C7—C8—C9—C4	0.3 (3)
C2—C3—C4—C9	−0.6 (2)	C7—C8—C9—C10	179.20 (17)
C2—C3—C4—C5	179.87 (15)	O1—C1—C10—C9	179.34 (14)
C9—C4—C5—C6	1.7 (2)	C2—C1—C10—C9	−0.2 (3)
C3—C4—C5—C6	−178.81 (17)	C4—C9—C10—C1	−0.1 (2)
C9—C4—C5—O2	−178.55 (14)	C8—C9—C10—C1	−179.04 (17)
C3—C4—C5—O2	1.0 (2)	C10—C1—O1—C11	3.4 (2)
O2—C5—C6—C7	178.69 (17)	C2—C1—O1—C11	−177.02 (14)
C4—C5—C6—C7	−1.6 (3)	C12—C11—O1—C1	−179.26 (14)
C5—C6—C7—C8	0.8 (3)	C6—C5—O2—C14	0.0 (3)
C6—C7—C8—C9	−0.1 (3)	C4—C5—O2—C14	−179.77 (14)
C3—C4—C9—C10	0.5 (2)	C15—C14—O2—C5	74.8 (2)
C5—C4—C9—C10	−179.96 (15)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C1–C4/C9/C10 and C4–C9 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cg1^i	0.97	2.75	3.602 (2)	147
C14—H14A···Cg2^ii	0.97	2.76	3.457 (2)	130

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.