3,12-Dimeth-oxy-5,6,9,10-tetra-hydro-[5]helicene-7,8-dicarbo-nitrile.

The complete molecule of the title compound, C26H20N2O2, is generated by a crystallographic twofold axis. The torsion angle between the terminal and central benzene rings is -32.5 (2)°. The torsion angle along the inner helical rim of the molecule is -18.8 (2)° with each other. The C⋯C distance between the terminal rings is 3.016 (2) Å. In the crystal, weak C-H⋯N hydrogen bonds are observed.

Related literature

For the application of a penta­helicene derivative as an emitter in an organic light-emitting diode, see: Sahasithiwat et al. (2010 ▶). For related structures, see: McIntosh et al. (1954 ▶); Wang et al. (1997 ▶); Stammel et al. (1999 ▶); Ogawa et al. (2003 ▶); Rajapakse et al. (2011 ▶). For the synthesis of the title compound, see: Mandal et al. (2006 ▶). For general information and applications of helicenes, see: Shen & Chen (2012 ▶); Gingras (2013 ▶).

Experimental

Crystal data

C26H20N2O2

M = 392.44

Monoclinic,

a = 17.9533 (7) Å

b = 13.5533 (7) Å

c = 8.1417 (4) Å

β = 95.785 (2)°

V = 1971.00 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.67 × 0.44 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.70, T max = 0.75

10904 measured reflections

2204 independent reflections

1674 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.137

S = 1.07

2204 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814014950/nr2052sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014950/nr2052Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814014950/nr2052Isup3.mol

CCDC reference: 1010118

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

C26H20N2O2	F(000) = 824
Mr = 392.44	Dx = 1.322 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.9533 (7) Å	Cell parameters from 3787 reflections
b = 13.5533 (7) Å	θ = 2.3–27.1°
c = 8.1417 (4) Å	µ = 0.08 mm−1
β = 95.785 (2)°	T = 296 K
V = 1971.00 (16) Å3	Block, green
Z = 4	0.67 × 0.44 × 0.26 mm

Bruker APEXII CCD diffractometer	1674 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.025
φ and ω scans	θmax = 27.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −23→21
Tmin = 0.70, Tmax = 0.75	k = −17→17
10904 measured reflections	l = −10→10
2204 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0693P)2 + 0.772P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2204 reflections	Δρmax = 0.18 e Å−3
136 parameters	Δρmin = −0.19 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
C4	0.18794 (7)	0.30146 (11)	0.13412 (18)	0.0409 (3)
H4	0.2399	0.3047	0.1479	0.049*
C10	0.03622 (7)	0.12362 (10)	0.22237 (18)	0.0374 (3)
C2	0.06956 (8)	0.37374 (11)	0.03575 (19)	0.0419 (4)
H2	0.0421	0.4247	−0.0174	0.050*
C8	0.07336 (7)	0.21339 (10)	0.16691 (17)	0.0370 (3)
O1	0.18785 (6)	0.46083 (8)	0.02479 (16)	0.0572 (3)
C9	0.15209 (7)	0.21797 (10)	0.18425 (17)	0.0382 (3)
C1	0.03382 (7)	0.29099 (10)	0.08781 (18)	0.0399 (3)
H1	−0.0181	0.2870	0.0695	0.048*
C6	0.15632 (8)	0.03662 (11)	0.1795 (2)	0.0465 (4)
H6A	0.1598	0.0358	0.0613	0.056*
H6B	0.1819	−0.0213	0.2269	0.056*
C7	0.03793 (8)	−0.05492 (10)	0.23454 (19)	0.0416 (4)
C3	0.14727 (8)	0.38012 (10)	0.06373 (18)	0.0416 (4)
C11	0.07496 (7)	0.03379 (10)	0.21240 (19)	0.0401 (3)
C5	0.19390 (7)	0.12912 (11)	0.2542 (2)	0.0465 (4)
H5A	0.1937	0.1280	0.3733	0.056*
H5B	0.2455	0.1318	0.2287	0.056*
C13	0.07734 (8)	−0.14666 (11)	0.2179 (2)	0.0476 (4)
N1	0.11026 (8)	−0.21725 (10)	0.2016 (2)	0.0659 (5)
C12	0.14758 (12)	0.54725 (14)	−0.0283 (3)	0.0749 (6)
H12A	0.1822	0.5981	−0.0518	0.112*
H12B	0.1184	0.5692	0.0572	0.112*
H12C	0.1150	0.5328	−0.1262	0.112*

	U11	U22	U33	U12	U13	U23
C4	0.0256 (6)	0.0491 (8)	0.0494 (8)	−0.0029 (6)	0.0100 (6)	−0.0070 (6)
C10	0.0260 (6)	0.0394 (7)	0.0466 (8)	−0.0002 (5)	0.0033 (5)	−0.0005 (6)
C2	0.0353 (7)	0.0443 (8)	0.0465 (8)	0.0021 (6)	0.0060 (6)	0.0025 (6)
C8	0.0259 (6)	0.0396 (7)	0.0460 (8)	0.0002 (5)	0.0068 (5)	−0.0018 (6)
O1	0.0440 (6)	0.0520 (7)	0.0778 (8)	−0.0107 (5)	0.0166 (6)	0.0084 (6)
C9	0.0268 (6)	0.0440 (8)	0.0446 (8)	0.0016 (5)	0.0068 (5)	−0.0044 (6)
C1	0.0266 (6)	0.0443 (7)	0.0489 (8)	0.0001 (6)	0.0043 (6)	−0.0007 (6)
C6	0.0294 (7)	0.0446 (8)	0.0664 (10)	0.0074 (6)	0.0086 (7)	−0.0007 (7)
C7	0.0345 (7)	0.0388 (7)	0.0507 (9)	0.0031 (6)	−0.0002 (6)	−0.0011 (6)
C3	0.0370 (7)	0.0448 (8)	0.0447 (8)	−0.0063 (6)	0.0128 (6)	−0.0021 (6)
C11	0.0284 (7)	0.0420 (8)	0.0497 (8)	0.0032 (5)	0.0028 (6)	−0.0007 (6)
C5	0.0251 (6)	0.0520 (9)	0.0623 (10)	0.0043 (6)	0.0043 (6)	0.0005 (7)
C13	0.0370 (8)	0.0427 (8)	0.0618 (10)	0.0005 (6)	−0.0008 (7)	−0.0022 (7)
N1	0.0529 (9)	0.0487 (8)	0.0946 (12)	0.0102 (7)	−0.0004 (8)	−0.0082 (8)
C12	0.0666 (12)	0.0661 (12)	0.0881 (15)	−0.0194 (9)	−0.0103 (10)	0.0366 (11)

C4—C3	1.383 (2)	C1—H1	0.9300
C4—C9	1.3836 (19)	C6—C11	1.5120 (19)
C4—H4	0.9300	C6—C5	1.521 (2)
C10—C11	1.4085 (18)	C6—H6A	0.9700
C10—C10i	1.418 (3)	C6—H6B	0.9700
C10—C8	1.4796 (19)	C7—C11	1.3943 (19)
C2—C1	1.3798 (19)	C7—C7i	1.410 (3)
C2—C3	1.393 (2)	C7—C13	1.444 (2)
C2—H2	0.9300	C5—H5A	0.9700
C8—C1	1.3903 (19)	C5—H5B	0.9700
C8—C9	1.4076 (18)	C13—N1	1.1392 (19)
O1—C3	1.3692 (17)	C12—H12A	0.9600
O1—C12	1.421 (2)	C12—H12B	0.9600
C9—C5	1.5005 (19)	C12—H12C	0.9600
C3—C4—C9	120.71 (12)	H6A—C6—H6B	108.1
C3—C4—H4	119.6	C11—C7—C7i	120.32 (8)
C9—C4—H4	119.6	C11—C7—C13	119.08 (13)
C11—C10—C10i	119.48 (8)	C7i—C7—C13	120.54 (8)
C11—C10—C8	116.93 (12)	O1—C3—C4	116.15 (12)
C10i—C10—C8	123.54 (7)	O1—C3—C2	123.99 (14)
C1—C2—C3	119.29 (13)	C4—C3—C2	119.85 (13)
C1—C2—H2	120.4	C7—C11—C10	119.56 (12)
C3—C2—H2	120.4	C7—C11—C6	121.77 (12)
C1—C8—C9	118.28 (12)	C10—C11—C6	118.67 (12)
C1—C8—C10	122.59 (12)	C9—C5—C6	108.96 (12)
C9—C8—C10	118.98 (12)	C9—C5—H5A	109.9
C3—O1—C12	117.57 (12)	C6—C5—H5A	109.9
C4—C9—C8	119.92 (13)	C9—C5—H5B	109.9
C4—C9—C5	122.58 (12)	C6—C5—H5B	109.9
C8—C9—C5	117.49 (12)	H5A—C5—H5B	108.3
C2—C1—C8	121.71 (13)	N1—C13—C7	177.50 (18)
C2—C1—H1	119.1	O1—C12—H12A	109.5
C8—C1—H1	119.1	O1—C12—H12B	109.5
C11—C6—C5	110.32 (12)	H12A—C12—H12B	109.5
C11—C6—H6A	109.6	O1—C12—H12C	109.5
C5—C6—H6A	109.6	H12A—C12—H12C	109.5
C11—C6—H6B	109.6	H12B—C12—H12C	109.5
C5—C6—H6B	109.6
C11—C10—C8—C1	145.00 (15)	C9—C4—C3—C2	−3.0 (2)
C10i—C10—C8—C1	−32.5 (3)	C1—C2—C3—O1	−176.54 (14)
C11—C10—C8—C9	−30.49 (19)	C1—C2—C3—C4	3.8 (2)
C10i—C10—C8—C9	152.05 (18)	C7i—C7—C11—C10	0.5 (3)
C3—C4—C9—C8	−1.3 (2)	C13—C7—C11—C10	177.68 (15)
C3—C4—C9—C5	177.21 (14)	C7i—C7—C11—C6	179.84 (17)
C1—C8—C9—C4	4.7 (2)	C13—C7—C11—C6	−3.0 (2)
C10—C8—C9—C4	−179.60 (13)	C10i—C10—C11—C7	8.9 (3)
C1—C8—C9—C5	−173.89 (13)	C8—C10—C11—C7	−168.68 (14)
C10—C8—C9—C5	1.79 (19)	C10i—C10—C11—C6	−170.49 (16)
C3—C2—C1—C8	−0.3 (2)	C8—C10—C11—C6	11.9 (2)
C9—C8—C1—C2	−3.9 (2)	C5—C6—C11—C7	−147.72 (15)
C10—C8—C1—C2	−179.43 (13)	C5—C6—C11—C10	31.6 (2)
C12—O1—C3—C4	−172.31 (16)	C4—C9—C5—C6	−136.89 (14)
C12—O1—C3—C2	8.0 (2)	C8—C9—C5—C6	41.68 (18)
C9—C4—C3—O1	177.34 (13)	C11—C6—C5—C9	−57.20 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N1ii	0.93	2.79	3.466 (2)	131
C4—H4···N1iii	0.93	2.86	3.742 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N1i	0.93	2.79	3.466 (2)	131
C4—H4⋯N1ii	0.93	2.86	3.742 (2)	160

Symmetry codes: (i) ; (ii) .