1,5-Bis(2,5-dimethyl-1H-pyrrol-1-yl)naphthalene.

In the title compound, C(22)H(22)N(2), the asymmetric unit contains one half-mol-ecule. A crystallographic inversion centre is located at the mid-point of the bond common to both rings, in the central naphthalene unit. Quantum-mechanical ab initio calculations on the isolated mol-ecule showed that the minimum energy configuration occurs when the naphthalene ring system and the pyrrolyl groups deviate only slightly from perpendicularity. In the crystal, due to the effects of crystal packing, the mol-ecule deviates by approximately 4° from the a priori expected ideal value of 90° [C-C-N-C torsion angle = 86.11 (15)°].

Related literature

For related compounds, see: Andrade et al. (2008 ▶); Ramos Silva et al. (2002 ▶); Sobral (2006 ▶); Sobral & Rocha Gonsalves (2001a ▶,b ▶). For the ab initio calculation method, see: Schmidt et al. (1993 ▶).

Experimental

Crystal data

C22H22N2

M = 314.42

Monoclinic,

a = 8.7562 (3) Å

b = 7.2806 (2) Å

c = 14.1380 (5) Å

β = 101.4721 (16)°

V = 883.30 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.30 × 0.30 × 0.02 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.892, T max = 0.999

23689 measured reflections

2415 independent reflections

1798 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.160

S = 1.11

2415 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809038999/pk2188sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038999/pk2188Isup2.hkl

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

C22H22N2	F(000) = 336
Mr = 314.42	Dx = 1.182 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8233 reflections
a = 8.7562 (3) Å	θ = 2.4–28.6°
b = 7.2806 (2) Å	µ = 0.07 mm−1
c = 14.1380 (5) Å	T = 293 K
β = 101.4721 (16)°	Plate, brown
V = 883.30 (5) Å3	0.30 × 0.30 × 0.02 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	2415 independent reflections
Radiation source: fine-focus sealed tube	1798 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 29.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −12→11
Tmin = 0.892, Tmax = 0.999	k = −10→9
23689 measured reflections	l = −18→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0861P)2 + 0.0939P] where P = (Fo2 + 2Fc2)/3
2415 reflections	(Δ/σ)max < 0.001
111 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.20 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
N1	−0.25783 (11)	0.16842 (14)	−0.15743 (7)	0.0413 (3)
C1	−0.37264 (14)	0.28237 (17)	−0.13576 (10)	0.0457 (3)
C2	−0.40388 (17)	0.41020 (19)	−0.20743 (11)	0.0581 (4)
H2	−0.4765	0.5046	−0.2117	0.070*
C4	−0.21687 (17)	0.2256 (2)	−0.24234 (10)	0.0543 (4)
C3	−0.3073 (2)	0.3747 (2)	−0.27363 (11)	0.0644 (5)
H3	−0.3054	0.4416	−0.3294	0.077*
C5	−0.4403 (2)	0.2558 (2)	−0.04885 (14)	0.0677 (5)
H5A	−0.5235	0.3419	−0.0496	0.102*
H5B	−0.3612	0.2752	0.0079	0.102*
H5C	−0.4800	0.1329	−0.0484	0.102*
C6	−0.0984 (3)	0.1270 (3)	−0.28455 (14)	0.0867 (6)
H6A	−0.0887	0.1846	−0.3441	0.130*
H6B	−0.1298	0.0015	−0.2966	0.130*
H6C	0.0001	0.1310	−0.2403	0.130*
C7	−0.03746 (12)	0.07020 (14)	−0.03141 (8)	0.0338 (3)
C8	−0.18058 (13)	0.02723 (15)	−0.09515 (8)	0.0374 (3)
C9	−0.24388 (15)	−0.14418 (17)	−0.09648 (10)	0.0472 (3)
H9	−0.3369	−0.1703	−0.1389	0.057*
C10	−0.16905 (15)	−0.28164 (17)	−0.03401 (10)	0.0478 (3)
H10	−0.2135	−0.3978	−0.0352	0.057*
C11	−0.03195 (14)	−0.24638 (15)	0.02834 (9)	0.0403 (3)
H11	0.0162	−0.3387	0.0691	0.048*

	U11	U22	U33	U12	U13	U23
N1	0.0373 (5)	0.0397 (5)	0.0418 (6)	0.0034 (4)	−0.0041 (4)	0.0032 (4)
C1	0.0380 (6)	0.0377 (6)	0.0544 (7)	0.0016 (5)	−0.0074 (5)	−0.0072 (5)
C2	0.0550 (9)	0.0415 (7)	0.0643 (9)	0.0071 (6)	−0.0209 (7)	−0.0012 (6)
C4	0.0542 (8)	0.0616 (9)	0.0425 (7)	0.0017 (6)	−0.0016 (6)	0.0083 (6)
C3	0.0725 (10)	0.0591 (9)	0.0505 (8)	−0.0008 (7)	−0.0144 (7)	0.0161 (7)
C5	0.0623 (10)	0.0612 (9)	0.0825 (11)	0.0101 (7)	0.0214 (8)	−0.0053 (8)
C6	0.0921 (14)	0.1113 (16)	0.0625 (10)	0.0227 (12)	0.0292 (10)	0.0146 (10)
C7	0.0322 (6)	0.0315 (5)	0.0362 (6)	0.0009 (4)	0.0033 (4)	0.0000 (4)
C8	0.0344 (6)	0.0360 (6)	0.0390 (6)	0.0030 (4)	0.0003 (5)	0.0012 (4)
C9	0.0376 (7)	0.0421 (6)	0.0551 (7)	−0.0048 (5)	−0.0071 (5)	−0.0012 (5)
C10	0.0444 (7)	0.0332 (6)	0.0611 (8)	−0.0075 (5)	−0.0012 (6)	0.0011 (5)
C11	0.0401 (6)	0.0316 (5)	0.0468 (7)	0.0005 (4)	0.0026 (5)	0.0042 (4)

N1—C4	1.3835 (17)	C6—H6A	0.9600
N1—C1	1.3840 (16)	C6—H6B	0.9600
N1—C8	1.4326 (14)	C6—H6C	0.9600
C1—C2	1.3628 (19)	C7—C11i	1.4164 (15)
C1—C5	1.479 (2)	C7—C8	1.4253 (15)
C2—C3	1.404 (3)	C7—C7i	1.426 (2)
C2—H2	0.9300	C8—C9	1.3642 (17)
C4—C3	1.365 (2)	C9—C10	1.4075 (18)
C4—C6	1.481 (2)	C9—H9	0.9300
C3—H3	0.9300	C10—C11	1.3649 (17)
C5—H5A	0.9600	C10—H10	0.9300
C5—H5B	0.9600	C11—C7i	1.4164 (15)
C5—H5C	0.9600	C11—H11	0.9300
C4—N1—C1	109.68 (11)	C4—C6—H6A	109.5
C4—N1—C8	125.23 (11)	C4—C6—H6B	109.5
C1—N1—C8	124.69 (11)	H6A—C6—H6B	109.5
C2—C1—N1	106.98 (13)	C4—C6—H6C	109.5
C2—C1—C5	130.75 (14)	H6A—C6—H6C	109.5
N1—C1—C5	122.26 (12)	H6B—C6—H6C	109.5
C1—C2—C3	108.15 (13)	C11i—C7—C8	122.42 (10)
C1—C2—H2	125.9	C11i—C7—C7i	119.26 (12)
C3—C2—H2	125.9	C8—C7—C7i	118.32 (12)
C3—C4—N1	106.65 (14)	C9—C8—C7	120.88 (10)
C3—C4—C6	131.51 (15)	C9—C8—N1	120.47 (10)
N1—C4—C6	121.82 (13)	C7—C8—N1	118.64 (10)
C4—C3—C2	108.53 (13)	C8—C9—C10	120.31 (11)
C4—C3—H3	125.7	C8—C9—H9	119.8
C2—C3—H3	125.7	C10—C9—H9	119.8
C1—C5—H5A	109.5	C11—C10—C9	120.76 (11)
C1—C5—H5B	109.5	C11—C10—H10	119.6
H5A—C5—H5B	109.5	C9—C10—H10	119.6
C1—C5—H5C	109.5	C10—C11—C7i	120.47 (11)
H5A—C5—H5C	109.5	C10—C11—H11	119.8
H5B—C5—H5C	109.5	C7i—C11—H11	119.8
C4—N1—C1—C2	0.28 (14)	C11i—C7—C8—C9	179.75 (12)
C8—N1—C1—C2	173.32 (11)	C7i—C7—C8—C9	−0.4 (2)
C4—N1—C1—C5	−179.96 (13)	C11i—C7—C8—N1	−0.83 (18)
C8—N1—C1—C5	−6.91 (19)	C7i—C7—C8—N1	179.03 (12)
N1—C1—C2—C3	−0.09 (15)	C4—N1—C8—C9	−101.92 (16)
C5—C1—C2—C3	−179.82 (15)	C1—N1—C8—C9	86.11 (15)
C1—N1—C4—C3	−0.36 (16)	C4—N1—C8—C7	78.66 (16)
C8—N1—C4—C3	−173.36 (11)	C1—N1—C8—C7	−93.32 (14)
C1—N1—C4—C6	−178.79 (15)	C7—C8—C9—C10	0.5 (2)
C8—N1—C4—C6	8.2 (2)	N1—C8—C9—C10	−178.89 (12)
N1—C4—C3—C2	0.30 (17)	C8—C9—C10—C11	−0.4 (2)
C6—C4—C3—C2	178.52 (17)	C9—C10—C11—C7i	0.1 (2)
C1—C2—C3—C4	−0.14 (17)