[6]Cyclo-2,7-naphthyl-ene: a redetermination.

Single crystals of a macrocyclic hydro-carbon, [6]cyclo-2,7-naphthyl-ene ([6]CNAP, C(60)H(36)) were prepared from anthracene melt with a prolonged time for the recrystallization. The crystal of improved quality led to the correction of the space-group assignment to Cmca from [Formula: see text] in the original determination [Nakanishi et al. (2011 ▶) Angew. Chem. Int. Ed.50, 5323-5326] and the refinement of anisotropic displacement parameters of all C atoms. The refined mol-ecular structure with C(2h) point symmetry indicated that the strain on the naphthyl rings of [6]CNAP is smallest among the congeners. Despite the large macrocyclic structure, mol-ecules are packed in a ubiquitous herringbone motif. A short C-C distance of 3.119 (4) Å was found in the stacking direction, and a short C-H distance of 2.80 Å was found in the inter-columnar contact.

Related literature

Superior quality crystals of the title compound were obtained by re-optimizing the crystallization conditions. For the synthesis and preceding crystallographic analysis, see: Nakanishi et al. (2011 ▶). For the original method of recrystallization, see: Miyahara & Shimizu (2001 ▶). For a review of C—H⋯π contacts in crystals, see: Nishio (2004 ▶).

Experimental

Crystal data

C60H36

M = 756.89

Orthorhombic,

a = 34.224 (6) Å

b = 7.4629 (14) Å

c = 15.131 (3) Å

V = 3864.7 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.40 × 0.12 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.686, T max = 0.996

20522 measured reflections

2234 independent reflections

1667 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.181

S = 1.06

2234 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and Yadokari-XG 2009 (Kabuto et al., 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023427/nr2007sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023427/nr2007Isup2.hkl

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

C60H36	F(000) = 1584
Mr = 756.89	Dx = 1.301 Mg m−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 5445 reflections
a = 34.224 (6) Å	θ = 2.4–27.2°
b = 7.4629 (14) Å	µ = 0.07 mm−1
c = 15.131 (3) Å	T = 100 K
V = 3864.7 (12) Å3	Plate, colourless
Z = 4	0.40 × 0.12 × 0.06 mm

Bruker APEXII CCD area-detector diffractometer	2234 independent reflections
Radiation source: Bruker TXS fine-focus rotating anode	1667 reflections with I > 2σ(I)
Bruker Helios multilayer confocal mirror	Rint = 0.035
Detector resolution: 8.333 pixels mm-1	θmax = 27.5°, θmin = 2.4°
φ and ω scans	h = −43→43
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
Tmin = 0.686, Tmax = 0.996	l = −19→19
20522 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0565P)2 + 7.0687P] where P = (Fo2 + 2Fc2)/3
2234 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.35 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.

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	0.28550 (9)	0.7008 (6)	0.37933 (17)	0.0855 (12)
H1	0.2623	0.6634	0.3504	0.103*
C2	0.28488 (8)	0.8521 (5)	0.43007 (18)	0.0805 (11)
H2	0.2610	0.9154	0.4371	0.097*
C3	0.31917 (7)	0.9174 (4)	0.47282 (14)	0.0599 (7)
C4	0.35317 (7)	0.8204 (3)	0.46178 (14)	0.0521 (6)
H3	0.3764	0.8613	0.4897	0.062*
C5	0.35467 (8)	0.6627 (4)	0.41049 (14)	0.0546 (7)
C6	0.32004 (9)	0.5987 (5)	0.36887 (15)	0.0705 (9)
C7	0.32231 (11)	0.4362 (5)	0.32059 (16)	0.0842 (12)
H4	0.2997	0.3918	0.2916	0.101*
C8	0.35645 (11)	0.3425 (4)	0.31496 (15)	0.0777 (11)
H5	0.3570	0.2332	0.2828	0.093*
C9	0.39145 (9)	0.4048 (3)	0.35623 (14)	0.0599 (8)
C10	0.38962 (8)	0.5646 (3)	0.40197 (13)	0.0518 (6)
H6	0.4127	0.6100	0.4286	0.062*
C11	0.46345 (13)	0.0185 (3)	0.35550 (17)	0.0872 (12)
H7	0.4628	−0.1088	0.3562	0.105*
C12	0.42913 (13)	0.1103 (4)	0.35358 (16)	0.0781 (11)
H8	0.4052	0.0460	0.3522	0.094*
C13	0.42846 (10)	0.3024 (3)	0.35367 (14)	0.0602 (8)
C14	0.46407 (8)	0.3892 (3)	0.35413 (14)	0.0542 (7)
H9	0.4643	0.5165	0.3534	0.065*
C15	0.5000	0.2979 (4)	0.35555 (19)	0.0556 (10)
C16	0.5000	0.1066 (4)	0.3565 (2)	0.0708 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0610 (18)	0.162 (4)	0.0339 (13)	−0.048 (2)	−0.0068 (12)	0.0195 (17)
C2	0.0528 (16)	0.151 (3)	0.0375 (13)	−0.0189 (18)	−0.0027 (11)	0.0297 (17)
C3	0.0481 (13)	0.100 (2)	0.0322 (11)	−0.0087 (13)	−0.0009 (9)	0.0234 (11)
C4	0.0553 (14)	0.0695 (15)	0.0314 (10)	−0.0175 (12)	−0.0064 (9)	0.0157 (10)
C5	0.0663 (16)	0.0706 (16)	0.0270 (10)	−0.0286 (13)	−0.0066 (10)	0.0130 (10)
C6	0.0719 (18)	0.114 (2)	0.0260 (10)	−0.0495 (17)	−0.0031 (10)	0.0138 (13)
C7	0.094 (2)	0.129 (3)	0.0301 (12)	−0.074 (2)	−0.0006 (13)	0.0028 (15)
C8	0.116 (3)	0.088 (2)	0.0281 (11)	−0.071 (2)	0.0065 (14)	−0.0042 (12)
C9	0.098 (2)	0.0553 (14)	0.0264 (10)	−0.0412 (15)	−0.0006 (11)	0.0023 (9)
C10	0.0732 (16)	0.0537 (13)	0.0286 (10)	−0.0308 (12)	−0.0056 (10)	0.0062 (9)
C11	0.197 (4)	0.0250 (12)	0.0396 (13)	−0.0237 (18)	0.0074 (18)	−0.0075 (10)
C12	0.160 (3)	0.0402 (14)	0.0340 (12)	−0.0427 (18)	0.0088 (16)	−0.0048 (10)
C13	0.114 (2)	0.0398 (12)	0.0267 (10)	−0.0318 (14)	0.0039 (12)	−0.0045 (9)
C14	0.106 (2)	0.0247 (9)	0.0321 (10)	−0.0139 (11)	0.0003 (11)	−0.0036 (8)
C15	0.114 (3)	0.0230 (14)	0.0300 (14)	0.000	0.000	−0.0045 (11)
C16	0.157 (4)	0.0237 (15)	0.0318 (16)	0.000	0.000	−0.0046 (12)

C1—C2	1.365 (5)	C8—H5	0.9500
C1—C6	1.416 (5)	C9—C10	1.381 (3)
C1—H1	0.9500	C9—C13	1.480 (4)
C2—C3	1.426 (4)	C10—H6	0.9500
C2—H2	0.9500	C11—C12	1.360 (5)
C3—C4	1.380 (3)	C11—C16	1.413 (4)
C3—C3i	1.482 (6)	C11—H7	0.9500
C4—C5	1.410 (4)	C12—C13	1.434 (4)
C4—H3	0.9500	C12—H8	0.9500
C5—C10	1.408 (4)	C13—C14	1.380 (4)
C5—C6	1.425 (3)	C14—C15	1.406 (3)
C6—C7	1.418 (5)	C14—H9	0.9500
C7—C8	1.364 (5)	C15—C14ii	1.406 (3)
C7—H4	0.9500	C15—C16	1.428 (4)
C8—C9	1.429 (4)	C16—C11ii	1.413 (4)
C2—C1—C6	121.4 (3)	C10—C9—C8	117.5 (3)
C2—C1—H1	119.3	C10—C9—C13	119.9 (2)
C6—C1—H1	119.3	C8—C9—C13	122.6 (3)
C1—C2—C3	121.7 (3)	C9—C10—C5	122.3 (2)
C1—C2—H2	119.2	C9—C10—H6	118.9
C3—C2—H2	119.2	C5—C10—H6	118.9
C4—C3—C2	117.4 (3)	C12—C11—C16	122.0 (2)
C4—C3—C3i	120.22 (15)	C12—C11—H7	119.0
C2—C3—C3i	122.4 (2)	C16—C11—H7	119.0
C3—C4—C5	122.3 (2)	C11—C12—C13	121.2 (3)
C3—C4—H3	118.8	C11—C12—H8	119.4
C5—C4—H3	118.8	C13—C12—H8	119.4
C10—C5—C4	121.0 (2)	C14—C13—C12	117.1 (3)
C10—C5—C6	119.4 (3)	C14—C13—C9	120.9 (2)
C4—C5—C6	119.5 (3)	C12—C13—C9	122.0 (3)
C1—C6—C7	124.3 (3)	C13—C14—C15	123.0 (2)
C1—C6—C5	117.7 (3)	C13—C14—H9	118.5
C7—C6—C5	118.0 (3)	C15—C14—H9	118.5
C8—C7—C6	121.2 (3)	C14ii—C15—C14	122.0 (3)
C8—C7—H4	119.4	C14ii—C15—C16	118.99 (13)
C6—C7—H4	119.4	C14—C15—C16	118.99 (13)
C7—C8—C9	121.6 (3)	C11ii—C16—C11	124.5 (4)
C7—C8—H5	119.2	C11ii—C16—C15	117.71 (19)
C9—C8—H5	119.2	C11—C16—C15	117.71 (19)
C6—C1—C2—C3	1.9 (4)	C4—C5—C10—C9	176.39 (19)
C1—C2—C3—C4	−0.7 (4)	C6—C5—C10—C9	−1.7 (3)
C1—C2—C3—C3i	179.2 (3)	C16—C11—C12—C13	−0.9 (4)
C2—C3—C4—C5	0.1 (3)	C11—C12—C13—C14	1.2 (4)
C3i—C3—C4—C5	−179.8 (2)	C11—C12—C13—C9	−176.8 (2)
C3—C4—C5—C10	−178.7 (2)	C10—C9—C13—C14	−33.1 (3)
C3—C4—C5—C6	−0.6 (3)	C8—C9—C13—C14	148.8 (2)
C2—C1—C6—C7	177.0 (2)	C10—C9—C13—C12	144.8 (2)
C2—C1—C6—C5	−2.3 (4)	C8—C9—C13—C12	−33.2 (3)
C10—C5—C6—C1	179.8 (2)	C12—C13—C14—C15	−0.8 (3)
C4—C5—C6—C1	1.7 (3)	C9—C13—C14—C15	177.2 (2)
C10—C5—C6—C7	0.4 (3)	C13—C14—C15—C14ii	178.65 (17)
C4—C5—C6—C7	−177.7 (2)	C13—C14—C15—C16	0.1 (4)
C1—C6—C7—C8	−178.5 (2)	C12—C11—C16—C11ii	−177.8 (2)
C5—C6—C7—C8	0.8 (4)	C12—C11—C16—C15	0.1 (4)
C6—C7—C8—C9	−0.9 (4)	C14ii—C15—C16—C11ii	−0.3 (4)
C7—C8—C9—C10	−0.3 (3)	C14—C15—C16—C11ii	178.3 (2)
C7—C8—C9—C13	177.8 (2)	C14ii—C15—C16—C11	−178.3 (2)
C8—C9—C10—C5	1.6 (3)	C14—C15—C16—C11	0.3 (4)
C13—C9—C10—C5	−176.57 (19)