2,2'-(Propane-2,2-di-yl)bis-(1H-pyrrole).

The title compound, C(11)H(14)N(2), crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The two mol-ecules differ only slightly, with the pyrrole rings being inclined to one another at a dihedral angle of 87.67 (8)° in mol-ecule A and 88.09 (7)° in mol-ecule B. In the crystal, there are no classical hydrogen bonds, but the two pyrrole NH groups of one mol-ecule are involved in N-H⋯π inter-actions with the pyrrole rings of the other mol-ecule. In this manner, a compact box-like arrangement of the two independent mol-ecules is formed.

Related literature

For substituted calix[4]pyrroles, see: Gale et al. (1998 ▶); Sessler & Davis (2001 ▶); Sessler et al. (2003 ▶). For the synthesis and crystal structure of meso-diethyl-bis­(2-pyrrol­yl)methane, see: Sobral et al. (2003 ▶). For inter­molecular inter­actions involving aromatic rings in biological systems, see: Meyer et al. (2003 ▶). For a spectroscopic analysis of N—H⋯π inter­actions in pyrroles, see: Dauster et al. (2008 ▶).

Experimental

Crystal data

C11H14N2

M = 174.24

Triclinic,

a = 8.4554 (8) Å

b = 9.2001 (8) Å

c = 13.2274 (11) Å

α = 99.802 (7)°

β = 95.321 (7)°

γ = 97.328 (7)°

V = 998.74 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 173 K

0.40 × 0.34 × 0.28 mm

Data collection

Stoe IPDS-2 diffractometer

15270 measured reflections

5385 independent reflections

3816 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.106

S = 1.02

5385 reflections

255 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Data collection: X-AREA (Stoe & Cie, 2009 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2009 ▶); 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., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809054701/is2506sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054701/is2506Isup2.hkl

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

C11H14N2	Z = 4
Mr = 174.24	F(000) = 376
Triclinic, P1	Dx = 1.159 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4554 (8) Å	Cell parameters from 10442 reflections
b = 9.2001 (8) Å	θ = 1.6–29.5°
c = 13.2274 (11) Å	µ = 0.07 mm−1
α = 99.802 (7)°	T = 173 K
β = 95.321 (7)°	Block, colourless
γ = 97.328 (7)°	0.40 × 0.34 × 0.28 mm
V = 998.74 (15) Å3

Stoe IPDS-2 diffractometer	3816 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
graphite	θmax = 29.2°, θmin = 1.6°
φ and ω scans	h = −11→11
15270 measured reflections	k = −12→12
5385 independent reflections	l = −18→18

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0549P)2 + 0.0012P] where P = (Fo2 + 2Fc2)/3
5385 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.12135 (12)	0.25140 (11)	0.31284 (8)	0.0249 (3)
N2	0.40689 (12)	0.01811 (11)	0.24234 (8)	0.0252 (3)
C1	0.13663 (14)	0.38021 (14)	0.38492 (10)	0.0312 (4)
C2	0.17507 (15)	0.34619 (16)	0.47962 (10)	0.0348 (4)
C3	0.18351 (15)	0.19174 (16)	0.46471 (9)	0.0311 (4)
C4	0.14934 (13)	0.13454 (13)	0.36055 (9)	0.0234 (3)
C5	0.24635 (14)	−0.03734 (12)	0.22005 (9)	0.0226 (3)
C6	0.22365 (16)	−0.10944 (14)	0.11865 (9)	0.0305 (4)
C7	0.37369 (18)	−0.09563 (15)	0.07953 (10)	0.0358 (4)
C8	0.48462 (16)	−0.01599 (14)	0.15732 (10)	0.0314 (4)
C9	0.13255 (15)	−0.02364 (14)	0.30167 (9)	0.0277 (3)
C10	−0.04155 (17)	−0.07156 (17)	0.24923 (13)	0.0470 (5)
C11	0.1699 (2)	−0.12827 (17)	0.37732 (13)	0.0479 (5)
N21	0.51399 (12)	0.37264 (11)	0.36601 (7)	0.0232 (3)
N22	0.32603 (13)	0.28069 (11)	0.11006 (7)	0.0253 (3)
C21	0.59997 (14)	0.28840 (14)	0.42014 (9)	0.0264 (3)
C22	0.73108 (15)	0.26137 (15)	0.37047 (10)	0.0308 (4)
C23	0.72320 (14)	0.33192 (14)	0.28313 (9)	0.0281 (4)
C24	0.58798 (13)	0.40056 (13)	0.28184 (8)	0.0225 (3)
C25	0.35755 (14)	0.42785 (13)	0.15697 (8)	0.0229 (3)
C26	0.21946 (16)	0.48825 (14)	0.13876 (9)	0.0298 (4)
C27	0.10133 (16)	0.37382 (15)	0.07998 (10)	0.0340 (4)
C28	0.17016 (15)	0.24721 (14)	0.06366 (9)	0.0307 (3)
C29	0.52308 (14)	0.49773 (13)	0.21071 (9)	0.0251 (3)
C30	0.51173 (19)	0.65164 (14)	0.27414 (11)	0.0381 (4)
C31	0.63878 (17)	0.51784 (17)	0.12898 (10)	0.0381 (4)
H1N	0.1032 (19)	0.2477 (18)	0.2475 (13)	0.040 (4)*
H2N	0.4531 (19)	0.0726 (18)	0.2990 (12)	0.040 (4)*
H1	0.12280	0.47620	0.37120	0.0370*
H2	0.19290	0.41380	0.54380	0.0420*
H3	0.20840	0.13690	0.51730	0.0370*
H6	0.12470	−0.15960	0.08150	0.0370*
H7	0.39370	−0.13470	0.01140	0.0430*
H8	0.59580	0.01080	0.15310	0.0380*
H10A	−0.11590	−0.06340	0.30180	0.0710*
H10B	−0.05400	−0.17510	0.21260	0.0710*
H10C	−0.06530	−0.00660	0.20000	0.0710*
H11A	0.09550	−0.12180	0.43000	0.0720*
H11B	0.28040	−0.09850	0.41070	0.0720*
H11C	0.15750	−0.23100	0.33940	0.0720*
H21N	0.4231 (19)	0.4002 (16)	0.3827 (11)	0.031 (4)*
H22N	0.3894 (19)	0.2146 (18)	0.1123 (11)	0.039 (4)*
H21	0.57330	0.25470	0.48130	0.0320*
H22	0.81210	0.20590	0.39070	0.0370*
H23	0.79840	0.33180	0.23400	0.0340*
H26	0.20540	0.58890	0.16150	0.0360*
H27	−0.00570	0.38380	0.05650	0.0410*
H28	0.11950	0.15250	0.02670	0.0370*
H30A	0.47170	0.71520	0.22810	0.0570*
H30B	0.61830	0.69770	0.30870	0.0570*
H30C	0.43790	0.64010	0.32610	0.0570*
H31A	0.64370	0.42070	0.08640	0.0570*
H31B	0.74620	0.56090	0.16360	0.0570*
H31C	0.60000	0.58470	0.08510	0.0570*

	U11	U22	U33	U12	U13	U23
N1	0.0216 (5)	0.0271 (5)	0.0262 (5)	0.0050 (4)	0.0023 (4)	0.0045 (4)
N2	0.0249 (5)	0.0242 (5)	0.0266 (5)	0.0033 (4)	0.0039 (4)	0.0051 (4)
C1	0.0204 (6)	0.0265 (6)	0.0442 (7)	0.0037 (5)	0.0068 (5)	−0.0019 (5)
C2	0.0263 (6)	0.0400 (7)	0.0321 (6)	−0.0005 (5)	0.0080 (5)	−0.0090 (5)
C3	0.0269 (6)	0.0430 (8)	0.0231 (6)	0.0032 (5)	0.0050 (4)	0.0058 (5)
C4	0.0187 (5)	0.0285 (6)	0.0244 (5)	0.0045 (4)	0.0055 (4)	0.0068 (4)
C5	0.0244 (5)	0.0184 (5)	0.0258 (5)	0.0029 (4)	0.0035 (4)	0.0059 (4)
C6	0.0395 (7)	0.0234 (6)	0.0267 (6)	0.0030 (5)	0.0002 (5)	0.0024 (5)
C7	0.0553 (9)	0.0276 (7)	0.0283 (6)	0.0115 (6)	0.0169 (6)	0.0051 (5)
C8	0.0332 (7)	0.0269 (6)	0.0402 (7)	0.0104 (5)	0.0174 (5)	0.0116 (5)
C9	0.0270 (6)	0.0264 (6)	0.0312 (6)	0.0027 (5)	0.0094 (5)	0.0071 (5)
C10	0.0282 (7)	0.0395 (8)	0.0639 (10)	−0.0074 (6)	0.0111 (6)	−0.0107 (7)
C11	0.0672 (11)	0.0390 (8)	0.0518 (9)	0.0195 (7)	0.0325 (8)	0.0256 (7)
N21	0.0186 (5)	0.0288 (5)	0.0227 (5)	0.0038 (4)	0.0016 (4)	0.0060 (4)
N22	0.0289 (5)	0.0225 (5)	0.0239 (5)	0.0058 (4)	−0.0029 (4)	0.0043 (4)
C21	0.0248 (6)	0.0302 (6)	0.0236 (5)	0.0013 (5)	−0.0040 (4)	0.0087 (5)
C22	0.0238 (6)	0.0332 (7)	0.0360 (7)	0.0079 (5)	−0.0029 (5)	0.0085 (5)
C23	0.0211 (6)	0.0336 (7)	0.0292 (6)	0.0037 (5)	0.0037 (4)	0.0047 (5)
C24	0.0211 (5)	0.0237 (6)	0.0209 (5)	0.0000 (4)	−0.0003 (4)	0.0034 (4)
C25	0.0283 (6)	0.0221 (6)	0.0186 (5)	0.0039 (4)	0.0003 (4)	0.0055 (4)
C26	0.0349 (7)	0.0250 (6)	0.0308 (6)	0.0094 (5)	−0.0012 (5)	0.0074 (5)
C27	0.0289 (6)	0.0382 (7)	0.0347 (7)	0.0056 (5)	−0.0074 (5)	0.0115 (6)
C28	0.0317 (6)	0.0303 (6)	0.0267 (6)	−0.0010 (5)	−0.0080 (5)	0.0063 (5)
C29	0.0275 (6)	0.0242 (6)	0.0223 (5)	0.0002 (4)	−0.0014 (4)	0.0057 (4)
C30	0.0508 (8)	0.0234 (6)	0.0354 (7)	0.0030 (6)	−0.0115 (6)	0.0029 (5)
C31	0.0351 (7)	0.0476 (8)	0.0315 (6)	−0.0054 (6)	0.0023 (5)	0.0163 (6)

N1—C1	1.3724 (17)	C10—H10C	0.9800
N1—C4	1.3705 (16)	C10—H10B	0.9800
N2—C5	1.3739 (16)	C10—H10A	0.9800
N2—C8	1.3655 (17)	C11—H11B	0.9800
N1—H1N	0.858 (17)	C11—H11A	0.9800
N2—H2N	0.856 (16)	C11—H11C	0.9800
N21—C21	1.3704 (16)	C21—C22	1.3683 (18)
N21—C24	1.3720 (14)	C22—C23	1.4186 (18)
N22—C25	1.3712 (15)	C23—C24	1.3750 (17)
N22—C28	1.3750 (17)	C24—C29	1.5170 (16)
N21—H21N	0.875 (16)	C25—C29	1.5192 (17)
N22—H22N	0.863 (16)	C25—C26	1.3744 (18)
C1—C2	1.3626 (19)	C26—C27	1.4211 (19)
C2—C3	1.413 (2)	C27—C28	1.3612 (19)
C3—C4	1.3781 (17)	C29—C31	1.5421 (18)
C4—C9	1.5118 (17)	C29—C30	1.5373 (18)
C5—C6	1.3757 (17)	C21—H21	0.9500
C5—C9	1.5115 (17)	C22—H22	0.9500
C6—C7	1.413 (2)	C23—H23	0.9500
C7—C8	1.3654 (19)	C26—H26	0.9500
C9—C11	1.541 (2)	C27—H27	0.9500
C9—C10	1.544 (2)	C28—H28	0.9500
C1—H1	0.9500	C30—H30A	0.9800
C2—H2	0.9500	C30—H30B	0.9800
C3—H3	0.9500	C30—H30C	0.9800
C6—H6	0.9500	C31—H31A	0.9800
C7—H7	0.9500	C31—H31B	0.9800
C8—H8	0.9500	C31—H31C	0.9800
C1—N1—C4	109.93 (10)	C9—C11—H11C	109.00
C5—N2—C8	110.24 (10)	H11A—C11—H11B	109.00
C1—N1—H1N	123.9 (11)	H11A—C11—H11C	109.00
C4—N1—H1N	126.1 (11)	H11B—C11—H11C	109.00
C5—N2—H2N	126.5 (11)	C9—C11—H11B	109.00
C8—N2—H2N	123.1 (11)	C9—C11—H11A	109.00
C21—N21—C24	110.16 (10)	N21—C21—C22	107.86 (11)
C25—N22—C28	110.04 (10)	C21—C22—C23	107.02 (11)
C21—N21—H21N	123.5 (9)	C22—C23—C24	108.20 (11)
C24—N21—H21N	126.3 (9)	C23—C24—C29	131.63 (10)
C28—N22—H22N	123.0 (11)	N21—C24—C23	106.75 (10)
C25—N22—H22N	126.8 (11)	N21—C24—C29	121.55 (10)
N1—C1—C2	107.93 (12)	N22—C25—C29	121.59 (11)
C1—C2—C3	107.31 (12)	C26—C25—C29	131.53 (11)
C2—C3—C4	108.08 (11)	N22—C25—C26	106.79 (10)
C3—C4—C9	130.99 (12)	C25—C26—C27	108.09 (11)
N1—C4—C9	122.17 (10)	C26—C27—C28	107.19 (12)
N1—C4—C3	106.75 (11)	N22—C28—C27	107.89 (11)
N2—C5—C6	106.70 (11)	C25—C29—C31	109.40 (10)
C6—C5—C9	131.40 (11)	C30—C29—C31	108.82 (11)
N2—C5—C9	121.74 (10)	C25—C29—C30	109.04 (10)
C5—C6—C7	107.85 (11)	C24—C29—C25	110.94 (10)
C6—C7—C8	107.59 (12)	C24—C29—C30	109.35 (10)
N2—C8—C7	107.61 (12)	C24—C29—C31	109.26 (10)
C4—C9—C5	111.44 (10)	N21—C21—H21	126.00
C10—C9—C11	109.12 (12)	C22—C21—H21	126.00
C5—C9—C10	109.09 (10)	C21—C22—H22	126.00
C5—C9—C11	108.66 (11)	C23—C22—H22	127.00
C4—C9—C10	109.10 (11)	C22—C23—H23	126.00
C4—C9—C11	109.41 (10)	C24—C23—H23	126.00
N1—C1—H1	126.00	C25—C26—H26	126.00
C2—C1—H1	126.00	C27—C26—H26	126.00
C3—C2—H2	126.00	C26—C27—H27	126.00
C1—C2—H2	126.00	C28—C27—H27	126.00
C4—C3—H3	126.00	N22—C28—H28	126.00
C2—C3—H3	126.00	C27—C28—H28	126.00
C7—C6—H6	126.00	C29—C30—H30A	109.00
C5—C6—H6	126.00	C29—C30—H30B	109.00
C6—C7—H7	126.00	C29—C30—H30C	109.00
C8—C7—H7	126.00	H30A—C30—H30B	110.00
N2—C8—H8	126.00	H30A—C30—H30C	109.00
C7—C8—H8	126.00	H30B—C30—H30C	109.00
C9—C10—H10A	109.00	C29—C31—H31A	109.00
C9—C10—H10B	109.00	C29—C31—H31B	109.00
C9—C10—H10C	109.00	C29—C31—H31C	109.00
H10B—C10—H10C	110.00	H31A—C31—H31B	109.00
H10A—C10—H10C	109.00	H31A—C31—H31C	110.00
H10A—C10—H10B	109.00	H31B—C31—H31C	109.00
C4—N1—C1—C2	0.14 (14)	N2—C5—C9—C10	170.37 (11)
C1—N1—C4—C3	−0.25 (13)	N2—C5—C9—C11	−70.77 (14)
C1—N1—C4—C9	176.69 (11)	C6—C5—C9—C10	−14.94 (19)
C8—N2—C5—C6	0.67 (14)	C6—C5—C9—C11	103.92 (15)
C8—N2—C5—C9	176.51 (11)	C5—C6—C7—C8	0.07 (16)
C5—N2—C8—C7	−0.63 (14)	C6—C7—C8—N2	0.34 (15)
C21—N21—C24—C29	−177.09 (10)	N21—C21—C22—C23	−0.10 (15)
C24—N21—C21—C22	−0.03 (13)	C21—C22—C23—C24	0.19 (15)
C21—N21—C24—C23	0.15 (13)	C22—C23—C24—N21	−0.21 (14)
C28—N22—C25—C26	−0.63 (13)	C22—C23—C24—C29	176.64 (12)
C28—N22—C25—C29	−177.43 (10)	N21—C24—C29—C25	−63.67 (14)
C25—N22—C28—C27	0.54 (14)	N21—C24—C29—C30	56.63 (15)
N1—C1—C2—C3	0.02 (14)	N21—C24—C29—C31	175.64 (11)
C1—C2—C3—C4	−0.17 (15)	C23—C24—C29—C25	119.88 (14)
C2—C3—C4—C9	−176.31 (12)	C23—C24—C29—C30	−119.82 (14)
C2—C3—C4—N1	0.25 (14)	C23—C24—C29—C31	−0.82 (18)
N1—C4—C9—C5	60.57 (15)	N22—C25—C26—C27	0.48 (13)
N1—C4—C9—C11	−179.26 (11)	C29—C25—C26—C27	176.83 (12)
C3—C4—C9—C5	−123.33 (14)	N22—C25—C29—C24	−47.82 (14)
N1—C4—C9—C10	−59.95 (15)	N22—C25—C29—C30	−168.30 (10)
C3—C4—C9—C11	−3.15 (19)	N22—C25—C29—C31	72.79 (14)
C3—C4—C9—C10	116.16 (15)	C26—C25—C29—C24	136.28 (13)
N2—C5—C9—C4	49.85 (15)	C26—C25—C29—C30	15.80 (17)
C9—C5—C6—C7	−175.73 (12)	C26—C25—C29—C31	−103.11 (15)
N2—C5—C6—C7	−0.44 (14)	C25—C26—C27—C28	−0.16 (14)
C6—C5—C9—C4	−135.46 (13)	C26—C27—C28—N22	−0.23 (14)

D	H	Centroid	N—H	H···Cg	D···Cg	N—H···Cg
N1	H1N	Cg4	0.86 (2)	2.534 (17)	3.2190 (12)	137.4 (14)
N2	H2N	Cg3	0.86 (2)	2.591 (17)	3.2425 (12)	133.7 (13)
N21	H21N	Cg1	0.88 (2)	2.523 (16)	3.1925 (12)	133.9 (12)
N22	H22N	Cg2	0.86 (2)	2.610 (17)	3.2440 (12)	131.3 (13)

Table 1

Geometry of N—H⋯π inter­actions (Å, °)

D	H	Centroid	N—H	H⋯Cg	D⋯Cg	N—H⋯Cg
N1	H1N	Cg4	0.86 (2)	2.534 (17)	3.2190 (12)	137.4 (14)
N2	H2N	Cg3	0.86 (2)	2.591 (17)	3.2425 (12)	133.7 (13)
N21	H21N	Cg1	0.88 (2)	2.523 (16)	3.1925 (12)	133.9 (12)
N22	H22N	Cg2	0.86 (2)	2.610 (17)	3.2440 (12)	131.3 (13)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/C1–C4, N2/C5–C8, N21/C21—C24 and N22/C25–C28 rings, respectively.