trans-1-Phenyl-pyrrolidine-2,5-dicarbo-nitrile.

In the title compound, C(12)H(11)N(3), the plane of the phenyl ring and the least-squares plane of the pyrrolidine ring enclose an angle of 14.30 (6)°. The intra-cyclic N atom features a nearly trigonal-planar coordination geometry due to π-inter-actions with the aromatic system. The pyrrolidine ring is present in a twist conformation for which the closest pucker descriptor is (C9)T(C8). Weak inter-molecular C-H⋯N and C-H⋯π contacts occur.

Related literature

For background to the synthesis, see: Han & Ofial (2009 ▶); Takahashi et al. (1986 ▶). For a related structure, see: Menezes et al. (2007 ▶). For puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C12H11N3

M = 197.24

Orthorhombic,

a = 9.1807 (1) Å

b = 14.5693 (2) Å

c = 15.7576 (2) Å

V = 2107.68 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 200 K

0.33 × 0.18 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer

16161 measured reflections

2413 independent reflections

2109 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.107

S = 1.06

2413 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Data collection: COLLECT (Hooft, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810001479/fl2285sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001479/fl2285Isup2.hkl

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

C12H11N3	F(000) = 832
Mr = 197.24	Dx = 1.243 (1) Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9019 reflections
a = 9.1807 (1) Å	θ = 3.1–27.5°
b = 14.5693 (2) Å	µ = 0.08 mm−1
c = 15.7576 (2) Å	T = 200 K
V = 2107.68 (5) Å3	Block, colourless
Z = 8	0.33 × 0.18 × 0.15 mm

Nonius KappaCCD diffractometer	2109 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.022
MONTEL, graded multilayered X-ray optics	θmax = 27.5°, θmin = 3.4°
Detector resolution: 9 pixels mm-1	h = −11→11
CCD; rotation images; thick slices, phi/ω–scan	k = −18→18
16161 measured reflections	l = −20→20
2413 independent 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.049P)2 + 0.5393P] where P = (Fo2 + 2Fc2)/3
2413 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.18 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 > 2σ(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	0.91889 (10)	0.12762 (7)	0.48710 (6)	0.0339 (2)
N2	0.63244 (13)	0.15665 (9)	0.34906 (8)	0.0515 (3)
N3	1.27530 (11)	0.14135 (8)	0.55151 (7)	0.0460 (3)
C1	0.84192 (11)	0.11277 (7)	0.56211 (6)	0.0289 (2)
C2	0.71584 (12)	0.05831 (8)	0.56245 (7)	0.0331 (3)
H2	0.6806	0.0329	0.5109	0.040*
C3	0.64254 (13)	0.04149 (8)	0.63784 (8)	0.0395 (3)
H3	0.5569	0.0049	0.6373	0.047*
C4	0.69229 (13)	0.07717 (9)	0.71358 (8)	0.0414 (3)
H4	0.6423	0.0647	0.7651	0.050*
C5	0.81566 (13)	0.13119 (9)	0.71352 (7)	0.0393 (3)
H5	0.8501	0.1561	0.7655	0.047*
C6	0.89031 (12)	0.14984 (8)	0.63898 (7)	0.0338 (3)
H6	0.9744	0.1878	0.6401	0.041*
C7	0.87833 (12)	0.08771 (7)	0.40605 (6)	0.0313 (2)
H7	0.8707	0.0195	0.4112	0.038*
C8	1.00567 (13)	0.11327 (8)	0.34813 (7)	0.0385 (3)
H8A	1.0857	0.0680	0.3527	0.046*
H8B	0.9742	0.1176	0.2882	0.046*
C9	1.05183 (14)	0.20663 (8)	0.38243 (8)	0.0405 (3)
H9A	0.9888	0.2561	0.3598	0.049*
H9B	1.1544	0.2202	0.3676	0.049*
C10	1.03301 (11)	0.19671 (7)	0.47859 (7)	0.0326 (3)
H10	1.0003	0.2562	0.5038	0.039*
C11	0.73934 (13)	0.12635 (8)	0.37363 (7)	0.0349 (3)
C12	1.16995 (12)	0.16549 (7)	0.51982 (7)	0.0342 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0323 (5)	0.0433 (5)	0.0262 (5)	−0.0116 (4)	0.0000 (4)	0.0001 (4)
N2	0.0473 (7)	0.0588 (7)	0.0483 (6)	0.0060 (5)	−0.0134 (5)	−0.0106 (5)
N3	0.0382 (6)	0.0456 (6)	0.0542 (7)	−0.0001 (5)	−0.0083 (5)	−0.0055 (5)
C1	0.0275 (5)	0.0320 (5)	0.0270 (5)	0.0013 (4)	−0.0005 (4)	0.0025 (4)
C2	0.0315 (6)	0.0356 (6)	0.0321 (5)	−0.0039 (4)	0.0000 (4)	−0.0001 (4)
C3	0.0342 (6)	0.0412 (6)	0.0432 (6)	−0.0030 (5)	0.0068 (5)	0.0056 (5)
C4	0.0421 (7)	0.0493 (7)	0.0327 (6)	0.0067 (5)	0.0094 (5)	0.0067 (5)
C5	0.0426 (7)	0.0476 (6)	0.0277 (5)	0.0067 (5)	−0.0022 (5)	−0.0020 (5)
C6	0.0311 (6)	0.0391 (6)	0.0311 (6)	0.0004 (4)	−0.0027 (4)	−0.0014 (4)
C7	0.0351 (6)	0.0322 (5)	0.0267 (5)	−0.0007 (4)	0.0003 (4)	0.0000 (4)
C8	0.0388 (6)	0.0453 (7)	0.0315 (6)	0.0038 (5)	0.0070 (5)	0.0045 (5)
C9	0.0384 (6)	0.0427 (6)	0.0405 (6)	−0.0041 (5)	0.0031 (5)	0.0128 (5)
C10	0.0290 (5)	0.0310 (5)	0.0379 (6)	−0.0032 (4)	0.0005 (4)	0.0036 (4)
C11	0.0387 (6)	0.0369 (6)	0.0289 (5)	−0.0030 (5)	−0.0031 (5)	−0.0057 (4)
C12	0.0328 (6)	0.0312 (5)	0.0388 (6)	−0.0052 (4)	0.0003 (5)	−0.0022 (4)

N1—C1	1.3939 (13)	C5—H5	0.9500
N1—C7	1.4519 (14)	C6—H6	0.9500
N1—C10	1.4591 (13)	C7—C11	1.4853 (16)
N2—C11	1.1437 (16)	C7—C8	1.5291 (15)
N3—C12	1.1438 (16)	C7—H7	1.0000
C1—C6	1.3987 (15)	C8—C9	1.5238 (17)
C1—C2	1.4034 (15)	C8—H8A	0.9900
C2—C3	1.3873 (15)	C8—H8B	0.9900
C2—H2	0.9500	C9—C10	1.5320 (16)
C3—C4	1.3796 (18)	C9—H9A	0.9900
C3—H3	0.9500	C9—H9B	0.9900
C4—C5	1.3791 (18)	C10—C12	1.4864 (15)
C4—H4	0.9500	C10—H10	1.0000
C5—C6	1.3868 (16)
C1—N1—C7	123.63 (9)	N1—C7—H7	110.2
C1—N1—C10	123.29 (9)	C11—C7—H7	110.2
C7—N1—C10	112.31 (8)	C8—C7—H7	110.2
N1—C1—C6	120.89 (10)	C9—C8—C7	102.62 (9)
N1—C1—C2	120.60 (9)	C9—C8—H8A	111.2
C6—C1—C2	118.49 (10)	C7—C8—H8A	111.2
C3—C2—C1	120.22 (10)	C9—C8—H8B	111.2
C3—C2—H2	119.9	C7—C8—H8B	111.2
C1—C2—H2	119.9	H8A—C8—H8B	109.2
C4—C3—C2	120.91 (11)	C8—C9—C10	103.60 (9)
C4—C3—H3	119.5	C8—C9—H9A	111.0
C2—C3—H3	119.5	C10—C9—H9A	111.0
C5—C4—C3	119.10 (11)	C8—C9—H9B	111.0
C5—C4—H4	120.5	C10—C9—H9B	111.0
C3—C4—H4	120.5	H9A—C9—H9B	109.0
C4—C5—C6	121.22 (11)	N1—C10—C12	110.86 (9)
C4—C5—H5	119.4	N1—C10—C9	103.71 (9)
C6—C5—H5	119.4	C12—C10—C9	111.46 (9)
C5—C6—C1	120.06 (11)	N1—C10—H10	110.2
C5—C6—H6	120.0	C12—C10—H10	110.2
C1—C6—H6	120.0	C9—C10—H10	110.2
N1—C7—C11	111.78 (9)	N2—C11—C7	179.49 (13)
N1—C7—C8	103.38 (9)	N3—C12—C10	179.91 (15)
C11—C7—C8	111.05 (9)
C7—N1—C1—C6	177.08 (10)	C10—N1—C7—C11	−102.29 (11)
C10—N1—C1—C6	−13.76 (16)	C1—N1—C7—C8	−172.55 (10)
C7—N1—C1—C2	−1.36 (16)	C10—N1—C7—C8	17.22 (12)
C10—N1—C1—C2	167.81 (10)	N1—C7—C8—C9	−33.54 (11)
N1—C1—C2—C3	177.94 (10)	C11—C7—C8—C9	86.48 (11)
C6—C1—C2—C3	−0.53 (16)	C7—C8—C9—C10	37.66 (11)
C1—C2—C3—C4	−0.45 (18)	C1—N1—C10—C12	76.32 (13)
C2—C3—C4—C5	0.83 (18)	C7—N1—C10—C12	−113.42 (10)
C3—C4—C5—C6	−0.22 (18)	C1—N1—C10—C9	−163.96 (10)
C4—C5—C6—C1	−0.78 (18)	C7—N1—C10—C9	6.30 (12)
N1—C1—C6—C5	−177.33 (10)	C8—C9—C10—N1	−27.35 (12)
C2—C1—C6—C5	1.14 (16)	C8—C9—C10—C12	91.97 (11)
C1—N1—C7—C11	67.93 (13)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N2i	0.95	2.70	3.5952 (17)	158
C8—H8B···N2ii	0.99	2.67	3.3777 (17)	129
C10—H10···N3iii	1.00	2.69	3.3748 (15)	126
C8—H8A···Cgi	0.99	2.74	3.6937 (13)	162
C9—H9B···Cgiv	0.99	2.88	3.5111 (13)	122

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N2i	0.95	2.70	3.5952 (17)	158
C8—H8B⋯N2ii	0.99	2.67	3.3777 (17)	129
C10—H10⋯N3iii	1.00	2.69	3.3748 (15)	126
C8—H8A⋯Cgi	0.99	2.74	3.6937 (13)	162
C9—H9B⋯Cgiv	0.99	2.88	3.5111 (13)	122

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .