2-[(1H-Pyrrol-2-yl)meth-yl]-1H-pyrrole.

In the title compound, C9H10N2, the two pyrrole ring planes are twisted by a dihedral angle of 69.07 (16)° and the C-C-C methane angle is 115.1 (2)°. In the crystal, mol-ecules are connected into layers in the bc plane by N-H⋯π inter-actions.

Related literature

For synthesis of symmetric and non-symmetric porphyrins, see: Shanmugathasan et al. (2000 ▶); Bonifazi et al. (2005 ▶); Fendt et al. (2009 ▶). For their applications as organometallic ligands, see: Ganesan et al. (2001 ▶); Gao et al. (2004 ▶).

Experimental

Crystal data

C9H10N2

M = 146.19

Monoclinic,

a = 6.048 (3) Å

b = 7.312 (4) Å

c = 9.024 (5) Å

β = 100.78 (1)°

V = 392.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 153 K

0.32 × 0.08 × 0.06 mm

Data collection

Rigaku SCX-Mini diffractometer with Mercury 2 CCD

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.976, T max = 0.996

4179 measured reflections

1786 independent reflections

1374 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.132

S = 1.05

1786 reflections

100 parameters

61 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) hkj, I. DOI: 10.1107/S1600536813028365/tk5264sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028365/tk5264Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028365/tk5264Isup3.cml

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

C9H10N2	F(000) = 156
Mr = 146.19	Dx = 1.238 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2yb	Cell parameters from 4189 reflections
a = 6.048 (3) Å	θ = 3.0–27.5°
b = 7.312 (4) Å	µ = 0.08 mm−1
c = 9.024 (5) Å	T = 153 K
β = 100.78 (1)°	Needle, colourless
V = 392.0 (4) Å3	0.32 × 0.08 × 0.06 mm
Z = 2

Rigaku SCX-Mini with Mercury 2 CCD diffractometer	1786 independent reflections
Radiation source: fine-focus sealed tube	1374 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→7
Tmin = 0.976, Tmax = 0.996	k = −9→9
4179 measured reflections	l = −11→11

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.049P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
1786 reflections	Δρmax = 0.19 e Å−3
100 parameters	Δρmin = −0.23 e Å−3
61 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

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. The direction of the twofold screw axis could not be reliably determined.

	x	y	z	Uiso*/Ueq
C1	0.2619 (4)	−0.0035 (4)	0.5615 (3)	0.0353 (6)
H1	0.3300	−0.0409	0.6603	0.042*
C2	0.3488 (4)	0.1182 (4)	0.4732 (3)	0.0331 (6)
H2	0.4887	0.1802	0.4991	0.040*
C3	0.1930 (4)	0.1352 (3)	0.3367 (3)	0.0298 (6)
H3	0.2088	0.2109	0.2538	0.036*
C4	0.0136 (4)	0.0222 (4)	0.3451 (2)	0.0284 (5)
C5	−0.2014 (4)	−0.0146 (4)	0.2387 (2)	0.0348 (6)
H5A	−0.3267	0.0374	0.2818	0.042*
H5B	−0.2242	−0.1486	0.2310	0.042*
C6	−0.2144 (4)	0.0606 (3)	0.0837 (3)	0.0301 (6)
C7	−0.3568 (4)	0.1863 (4)	0.0037 (3)	0.0342 (6)
H7	−0.4721	0.2516	0.0396	0.041*
C8	−0.3029 (4)	0.2019 (4)	−0.1402 (3)	0.0362 (6)
H8	−0.3761	0.2785	−0.2195	0.043*
C9	−0.1268 (4)	0.0876 (4)	−0.1462 (2)	0.0367 (6)
H9	−0.0530	0.0711	−0.2294	0.044*
N1	0.0597 (4)	−0.0620 (3)	0.4825 (2)	0.0344 (6)
H1N	−0.0283	−0.1423	0.5153	0.041*
N2	−0.0764 (3)	0.0011 (3)	−0.0094 (2)	0.0336 (5)
H2N	0.0302	−0.0813	0.0148	0.040*

	U11	U22	U33	U12	U13	U23
C1	0.0380 (14)	0.0427 (15)	0.0244 (12)	0.0079 (13)	0.0037 (11)	−0.0002 (12)
C2	0.0322 (13)	0.0322 (14)	0.0356 (13)	−0.0001 (11)	0.0082 (11)	−0.0078 (11)
C3	0.0366 (13)	0.0265 (13)	0.0292 (12)	−0.0002 (10)	0.0135 (11)	0.0000 (10)
C4	0.0349 (12)	0.0269 (13)	0.0249 (11)	0.0027 (10)	0.0096 (10)	0.0001 (9)
C5	0.0311 (12)	0.0358 (14)	0.0388 (14)	−0.0030 (11)	0.0103 (11)	0.0009 (11)
C6	0.0281 (12)	0.0290 (14)	0.0322 (13)	−0.0035 (10)	0.0030 (10)	−0.0048 (10)
C7	0.0248 (13)	0.0328 (14)	0.0438 (15)	0.0010 (11)	0.0031 (11)	0.0001 (11)
C8	0.0343 (14)	0.0296 (14)	0.0394 (14)	−0.0002 (11)	−0.0070 (12)	0.0034 (11)
C9	0.0459 (14)	0.0375 (16)	0.0248 (13)	−0.0032 (13)	0.0016 (11)	−0.0026 (11)
N1	0.0388 (12)	0.0334 (13)	0.0323 (11)	−0.0030 (10)	0.0100 (10)	0.0038 (9)
N2	0.0371 (11)	0.0287 (11)	0.0345 (11)	0.0064 (10)	0.0058 (9)	0.0006 (9)

C1—C2	1.363 (4)	C5—H5B	0.9900
C1—N1	1.364 (3)	C6—N2	1.361 (3)
C1—H1	0.9500	C6—C7	1.370 (3)
C2—C3	1.410 (3)	C7—C8	1.402 (3)
C2—H2	0.9500	C7—H7	0.9500
C3—C4	1.377 (3)	C8—C9	1.363 (3)
C3—H3	0.9500	C8—H8	0.9500
C4—N1	1.365 (3)	C9—N2	1.369 (3)
C4—C5	1.490 (3)	C9—H9	0.9500
C5—C6	1.491 (3)	N1—H1N	0.8800
C5—H5A	0.9900	N2—H2N	0.8800
C2—C1—N1	107.8 (2)	N2—C6—C7	106.7 (2)
C2—C1—H1	126.1	N2—C6—C5	122.0 (2)
N1—C1—H1	126.1	C7—C6—C5	131.2 (2)
C1—C2—C3	107.5 (2)	C6—C7—C8	108.1 (2)
C1—C2—H2	126.3	C6—C7—H7	125.9
C3—C2—H2	126.3	C8—C7—H7	125.9
C4—C3—C2	107.7 (2)	C9—C8—C7	107.8 (2)
C4—C3—H3	126.2	C9—C8—H8	126.1
C2—C3—H3	126.2	C7—C8—H8	126.1
N1—C4—C3	107.0 (2)	C8—C9—N2	107.0 (2)
N1—C4—C5	120.6 (2)	C8—C9—H9	126.5
C3—C4—C5	132.4 (2)	N2—C9—H9	126.5
C4—C5—C6	115.1 (2)	C1—N1—C4	110.1 (2)
C4—C5—H5A	108.5	C1—N1—H1N	124.9
C6—C5—H5A	108.5	C4—N1—H1N	124.9
C4—C5—H5B	108.5	C6—N2—C9	110.5 (2)
C6—C5—H5B	108.5	C6—N2—H2N	124.8
H5A—C5—H5B	107.5	C9—N2—H2N	124.8
N1—C1—C2—C3	0.5 (3)	C5—C6—C7—C8	−177.2 (2)
C1—C2—C3—C4	−0.1 (3)	C6—C7—C8—C9	−0.7 (3)
C2—C3—C4—N1	−0.4 (3)	C7—C8—C9—N2	1.1 (3)
C2—C3—C4—C5	178.4 (3)	C2—C1—N1—C4	−0.8 (3)
N1—C4—C5—C6	−170.1 (2)	C3—C4—N1—C1	0.7 (3)
C3—C4—C5—C6	11.2 (4)	C5—C4—N1—C1	−178.3 (2)
C4—C5—C6—N2	64.4 (3)	C7—C6—N2—C9	0.6 (3)
C4—C5—C6—C7	−118.6 (3)	C5—C6—N2—C9	178.2 (2)
N2—C6—C7—C8	0.1 (3)	C8—C9—N2—C6	−1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cg1i	0.88	2.53	3.357 (3)	156
N2—H2N···Cg2ii	0.88	2.53	3.363 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C1–C4 and N2/C6–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cg1i	0.88	2.53	3.357 (3)	156
N2—H2N⋯Cg2ii	0.88	2.53	3.363 (3)	159

Symmetry codes: (i) ; (ii) .