2,3-Bis(prop-2-yn-yloxy)naphthalene.

In the crystal structure of the title compound, C(16)H(12)O(2), no classical hydrogen bonds or aromatic π-π stacking inter-actions were observed. The mol-ecules are linked into a three-dimensional framework by a combination of C-H⋯O and C-H⋯π(arene) hydrogen bonds.

Related literature

For related structures, see: Zhang et al. (2008 ▶); Ghosh et al. (2007 ▶); Wang & Kong (2007 ▶). For the synthesis, see: Burchell et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For π–π stacking inter­actions, see: Steed & Atwood (2000 ▶).

Experimental

Crystal data

C16H12O2

M = 236.26

Orthorhombic,

a = 8.2921 (12) Å

b = 9.0457 (14) Å

c = 33.070 (5) Å

V = 2480.5 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.18 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.984, T max = 0.989

12468 measured reflections

2182 independent reflections

1782 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.101

S = 1.04

2182 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037549/bv2111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037549/bv2111Isup2.hkl

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

C16H12O2	F000 = 992
Mr = 236.26	Dx = 1.265 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3821 reflections
a = 8.2921 (12) Å	θ = 2.8–25.7º
b = 9.0457 (14) Å	µ = 0.08 mm−1
c = 33.070 (5) Å	T = 298 (2) K
V = 2480.5 (6) Å3	Block, colourless
Z = 8	0.18 × 0.16 × 0.15 mm

Bruker SMART APEXII CCD area-detector diffractometer	2182 independent reflections
Radiation source: fine-focus sealed tube	1782 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 298(2) K	θmax = 25.0º
ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.984, Tmax = 0.989	k = −10→10
12468 measured reflections	l = −39→29

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.338P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2182 reflections	Δρmax = 0.17 e Å−3
163 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	−0.1360 (2)	−0.0848 (2)	0.32753 (6)	0.0752 (6)
H1	−0.1425	−0.1672	0.3108	0.090*
C2	−0.1277 (2)	0.01867 (18)	0.34856 (5)	0.0574 (4)
C3	−0.1181 (2)	0.14633 (16)	0.37505 (5)	0.0554 (4)
H3A	−0.2249	0.1865	0.3798	0.066*
H3B	−0.0720	0.1182	0.4009	0.066*
C4	0.00170 (15)	0.38601 (15)	0.37523 (4)	0.0400 (3)
C5	−0.05860 (17)	0.42250 (16)	0.41224 (4)	0.0462 (4)
H5	−0.1182	0.3532	0.4267	0.055*
C6	−0.03174 (17)	0.56457 (16)	0.42903 (4)	0.0451 (4)
C7	−0.0984 (2)	0.60874 (19)	0.46649 (4)	0.0586 (4)
H7	−0.1609	0.5422	0.4811	0.070*
C8	−0.0727 (3)	0.7468 (2)	0.48143 (5)	0.0703 (5)
H8	−0.1182	0.7741	0.5060	0.084*
C9	0.0218 (2)	0.8480 (2)	0.45997 (5)	0.0696 (5)
H9	0.0401	0.9417	0.4706	0.084*
C10	0.0875 (2)	0.80997 (18)	0.42353 (5)	0.0577 (4)
H10	0.1500	0.8782	0.4095	0.069*
C11	0.06147 (17)	0.66812 (16)	0.40699 (4)	0.0443 (3)
C12	0.12274 (17)	0.62803 (15)	0.36856 (4)	0.0436 (3)
H12	0.1830	0.6959	0.3538	0.052*
C13	0.09452 (16)	0.49128 (15)	0.35298 (4)	0.0391 (3)
C14	0.24207 (18)	0.53826 (15)	0.29190 (4)	0.0447 (3)
H14A	0.3080	0.4809	0.2735	0.054*
H14B	0.3139	0.5947	0.3092	0.054*
C15	0.14206 (18)	0.64031 (16)	0.26860 (4)	0.0448 (4)
C16	0.0667 (2)	0.71916 (18)	0.24743 (5)	0.0575 (4)
H16	0.0073	0.7814	0.2307	0.069*
O1	−0.01832 (12)	0.25415 (10)	0.35571 (3)	0.0479 (3)
O2	0.14871 (12)	0.43928 (10)	0.31646 (3)	0.0471 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0882 (14)	0.0598 (11)	0.0778 (12)	−0.0163 (10)	0.0254 (11)	−0.0032 (10)
C2	0.0584 (10)	0.0467 (9)	0.0672 (10)	−0.0065 (7)	0.0180 (8)	0.0088 (8)
C3	0.0586 (10)	0.0444 (8)	0.0631 (9)	−0.0032 (7)	0.0164 (8)	0.0104 (7)
C4	0.0354 (7)	0.0398 (7)	0.0448 (8)	0.0031 (6)	0.0005 (6)	0.0047 (6)
C5	0.0454 (8)	0.0499 (8)	0.0433 (8)	0.0030 (7)	0.0040 (6)	0.0117 (7)
C6	0.0448 (8)	0.0544 (9)	0.0361 (7)	0.0091 (7)	−0.0050 (6)	0.0042 (6)
C7	0.0660 (10)	0.0696 (11)	0.0403 (8)	0.0089 (8)	0.0054 (8)	0.0055 (8)
C8	0.0896 (14)	0.0803 (13)	0.0410 (8)	0.0154 (11)	0.0053 (9)	−0.0092 (8)
C9	0.0884 (13)	0.0660 (11)	0.0545 (10)	0.0014 (10)	−0.0006 (9)	−0.0156 (9)
C10	0.0643 (10)	0.0572 (9)	0.0517 (9)	−0.0036 (8)	−0.0007 (8)	−0.0081 (7)
C11	0.0418 (8)	0.0508 (8)	0.0403 (7)	0.0042 (6)	−0.0051 (6)	−0.0007 (6)
C12	0.0418 (8)	0.0453 (8)	0.0438 (8)	−0.0042 (6)	0.0031 (6)	0.0029 (6)
C13	0.0345 (7)	0.0440 (7)	0.0388 (7)	0.0025 (6)	0.0021 (6)	0.0022 (6)
C14	0.0452 (8)	0.0438 (7)	0.0453 (7)	−0.0025 (6)	0.0115 (7)	0.0018 (6)
C15	0.0497 (8)	0.0442 (8)	0.0405 (7)	−0.0073 (7)	0.0029 (7)	−0.0073 (6)
C16	0.0616 (10)	0.0558 (9)	0.0552 (9)	−0.0044 (8)	−0.0124 (8)	0.0009 (8)
O1	0.0499 (6)	0.0404 (5)	0.0535 (6)	−0.0050 (4)	0.0135 (5)	0.0027 (4)
O2	0.0535 (6)	0.0423 (5)	0.0454 (5)	−0.0060 (5)	0.0140 (5)	−0.0010 (4)

C1—C2	1.168 (2)	C8—H8	0.9300
C1—H1	0.9300	C9—C10	1.367 (2)
C2—C3	1.452 (2)	C9—H9	0.9300
C3—O1	1.4299 (16)	C10—C11	1.412 (2)
C3—H3A	0.9700	C10—H10	0.9300
C3—H3B	0.9700	C11—C12	1.416 (2)
C4—C5	1.363 (2)	C12—C13	1.3603 (19)
C4—O1	1.3663 (16)	C12—H12	0.9300
C4—C13	1.4285 (18)	C13—O2	1.3718 (15)
C5—C6	1.418 (2)	C14—O2	1.4354 (16)
C5—H5	0.9300	C14—C15	1.461 (2)
C6—C7	1.414 (2)	C14—H14A	0.9700
C6—C11	1.416 (2)	C14—H14B	0.9700
C7—C8	1.360 (2)	C15—C16	1.179 (2)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.399 (3)
C2—C1—H1	180.0	C10—C9—H9	119.8
C1—C2—C3	179.39 (17)	C8—C9—H9	119.8
O1—C3—C2	107.72 (12)	C9—C10—C11	120.64 (16)
O1—C3—H3A	110.2	C9—C10—H10	119.7
C2—C3—H3A	110.2	C11—C10—H10	119.7
O1—C3—H3B	110.2	C10—C11—C12	121.72 (14)
C2—C3—H3B	110.2	C10—C11—C6	119.03 (13)
H3A—C3—H3B	108.5	C12—C11—C6	119.23 (13)
C5—C4—O1	126.24 (12)	C13—C12—C11	120.74 (13)
C5—C4—C13	119.93 (13)	C13—C12—H12	119.6
O1—C4—C13	113.83 (11)	C11—C12—H12	119.6
C4—C5—C6	120.91 (13)	C12—C13—O2	126.08 (12)
C4—C5—H5	119.5	C12—C13—C4	120.25 (12)
C6—C5—H5	119.5	O2—C13—C4	113.67 (11)
C7—C6—C11	118.51 (14)	O2—C14—C15	112.73 (12)
C7—C6—C5	122.53 (14)	O2—C14—H14A	109.0
C11—C6—C5	118.93 (12)	C15—C14—H14A	109.0
C8—C7—C6	121.10 (16)	O2—C14—H14B	109.0
C8—C7—H7	119.4	C15—C14—H14B	109.0
C6—C7—H7	119.4	H14A—C14—H14B	107.8
C7—C8—C9	120.29 (16)	C16—C15—C14	175.37 (15)
C7—C8—H8	119.9	C15—C16—H16	180.0
C9—C8—H8	119.9	C4—O1—C3	117.03 (11)
C10—C9—C8	120.41 (17)	C13—O2—C14	117.45 (10)
O1—C4—C5—C6	−178.85 (12)	C10—C11—C12—C13	−179.18 (14)
C13—C4—C5—C6	0.5 (2)	C6—C11—C12—C13	−0.7 (2)
C4—C5—C6—C7	177.07 (13)	C11—C12—C13—O2	−179.26 (12)
C4—C5—C6—C11	−1.0 (2)	C11—C12—C13—C4	0.2 (2)
C11—C6—C7—C8	−0.7 (2)	C5—C4—C13—C12	−0.1 (2)
C5—C6—C7—C8	−178.81 (15)	O1—C4—C13—C12	179.33 (12)
C6—C7—C8—C9	−0.5 (3)	C5—C4—C13—O2	179.43 (12)
C7—C8—C9—C10	0.9 (3)	O1—C4—C13—O2	−1.12 (16)
C8—C9—C10—C11	−0.2 (3)	C5—C4—O1—C3	3.1 (2)
C9—C10—C11—C12	177.43 (15)	C13—C4—O1—C3	−176.35 (12)
C9—C10—C11—C6	−1.0 (2)	C2—C3—O1—C4	177.75 (12)
C7—C6—C11—C10	1.4 (2)	C12—C13—O2—C14	−1.0 (2)
C5—C6—C11—C10	179.60 (13)	C4—C13—O2—C14	179.51 (11)
C7—C6—C11—C12	−177.05 (13)	C15—C14—O2—C13	−81.84 (15)
C5—C6—C11—C12	1.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2i	0.93	2.48	3.409 (2)	177
C3—H3A···Cg1ii	0.97	2.95	3.634 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4–C6/C11–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O2i	0.93	2.48	3.409 (2)	177
C3—H3A⋯Cg1ii	0.97	2.95	3.634 (2)	129

Symmetry codes: (i) ; (ii) .