(1-Benzyl­piperidin-4-yl­idene)­aceto­nitrile

The title compound, C₁₄H₁₆N₂, crystallizes in a monoclinc unit cell. All bond lengths and angles are normal. The crystal structure is stabilized by van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.065
• wR factor = 0.158
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.99 Deg.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C9
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C6     -   C7       =       1.43 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         25
            C3  -C6  -C7  -N2    -81.00100.00   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT and SHELXTL (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-benzylpiperidin-4-ylideneacetonitrile

Crystal data

C14H16N2	F(000) = 456
Mr = 212.29	Dx = 1.155 Mg m^−3
Monoclinic, P21/c	Melting point: 363 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.442 (2) Å	Cell parameters from 6062 reflections
b = 15.681 (5) Å	θ = 3.2–19.1°
c = 12.120 (4) Å	µ = 0.07 mm^−1
β = 94.579 (6)°	T = 298 K
V = 1220.5 (7) Å^3	Block, colorless
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2142 independent reflections
Radiation source: fine-focus sealed tube	1128 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 100x100 microns pixels mm^-1	θmax = 25.0°, θmin = 2.6°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→18
Tmin = 0.986, Tmax = 0.993	l = −12→14
5816 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.039P] where P = (Fo^2 + 2Fc^2)/3
2142 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.11 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.3558 (3)	0.36478 (13)	−0.00249 (16)	0.0511 (6)
N2	0.6668 (5)	0.4098 (2)	−0.4414 (2)	0.1142 (12)
C10	−0.0113 (5)	0.2740 (2)	0.1620 (2)	0.0739 (9)
H10	−0.0571	0.2367	0.1056	0.089*
C9	0.1809 (4)	0.31212 (18)	0.1601 (2)	0.0528 (7)
C14	0.2454 (5)	0.36650 (18)	0.2450 (2)	0.0700 (9)
H14	0.3753	0.3923	0.2453	0.084*
C13	0.1215 (7)	0.3833 (2)	0.3294 (3)	0.0923 (12)
H13	0.1665	0.4203	0.3864	0.111*
C12	−0.0725 (7)	0.3442 (3)	0.3283 (3)	0.1019 (15)
H12	−0.1589	0.3551	0.3846	0.122*
C11	−0.1350 (5)	0.2903 (3)	0.2452 (3)	0.0988 (13)
H11	−0.2645	0.2640	0.2449	0.119*
C8	0.3189 (4)	0.29198 (19)	0.0697 (2)	0.0664 (8)
H8B	0.4518	0.2717	0.1029	0.080*
H8A	0.2563	0.2461	0.0248	0.080*
C5	0.1667 (4)	0.38653 (19)	−0.0702 (2)	0.0621 (8)
H5B	0.0583	0.4015	−0.0225	0.074*
H5A	0.1197	0.3373	−0.1137	0.074*
C4	0.2020 (4)	0.4607 (2)	−0.1473 (2)	0.0712 (9)
H4B	0.0767	0.4706	−0.1955	0.085*
H4A	0.2317	0.5120	−0.1041	0.085*
C3	0.3790 (4)	0.44206 (17)	−0.2154 (2)	0.0553 (7)
C2	0.5702 (4)	0.4165 (2)	−0.1480 (2)	0.0661 (9)
H2B	0.6233	0.4644	−0.1036	0.079*
H2A	0.6762	0.3995	−0.1961	0.079*
C1	0.5218 (4)	0.3429 (2)	−0.0730 (2)	0.0680 (9)
H1B	0.4799	0.2937	−0.1179	0.082*
H1A	0.6464	0.3277	−0.0270	0.082*
C6	0.3615 (5)	0.44485 (19)	−0.3257 (2)	0.0700 (9)
H6	0.2342	0.4601	−0.3619	0.084*
C7	0.5312 (6)	0.4252 (2)	−0.3901 (2)	0.0771 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0458 (13)	0.0605 (16)	0.0479 (12)	0.0057 (11)	0.0097 (11)	0.0085 (11)
N2	0.162 (3)	0.110 (3)	0.079 (2)	0.030 (2)	0.062 (2)	0.0120 (18)
C10	0.067 (2)	0.088 (3)	0.066 (2)	−0.0084 (19)	−0.0001 (17)	0.0214 (17)
C9	0.0535 (17)	0.0553 (19)	0.0501 (16)	0.0034 (15)	0.0072 (13)	0.0137 (14)
C14	0.086 (2)	0.062 (2)	0.062 (2)	−0.0039 (18)	0.0057 (18)	0.0047 (16)
C13	0.147 (4)	0.073 (3)	0.058 (2)	0.022 (3)	0.013 (2)	0.0052 (18)
C12	0.135 (4)	0.107 (4)	0.072 (3)	0.052 (3)	0.054 (3)	0.039 (2)
C11	0.075 (2)	0.130 (4)	0.095 (3)	0.008 (2)	0.029 (2)	0.052 (3)
C8	0.077 (2)	0.064 (2)	0.0595 (17)	0.0102 (16)	0.0121 (15)	0.0088 (15)
C5	0.0510 (17)	0.081 (2)	0.0551 (16)	0.0066 (16)	0.0104 (14)	0.0093 (15)
C4	0.073 (2)	0.087 (3)	0.0556 (18)	0.0210 (18)	0.0159 (16)	0.0174 (16)
C3	0.0649 (19)	0.0502 (18)	0.0521 (17)	−0.0037 (14)	0.0128 (15)	0.0037 (14)
C2	0.0578 (19)	0.090 (3)	0.0518 (16)	−0.0054 (16)	0.0150 (14)	−0.0014 (16)
C1	0.0550 (18)	0.089 (2)	0.0619 (18)	0.0165 (16)	0.0141 (15)	0.0070 (17)
C6	0.086 (2)	0.070 (2)	0.0548 (18)	0.0048 (18)	0.0135 (16)	0.0065 (16)
C7	0.123 (3)	0.063 (2)	0.0487 (18)	0.006 (2)	0.0258 (19)	0.0057 (16)

Geometric parameters (Å, º)

N1—C5	1.454 (3)	C8—H8A	0.9700
N1—C1	1.462 (3)	C5—C4	1.520 (4)
N1—C8	1.469 (3)	C5—H5B	0.9700
N2—C7	1.138 (4)	C5—H5A	0.9700
C10—C11	1.358 (4)	C4—C3	1.489 (3)
C10—C9	1.377 (4)	C4—H4B	0.9700
C10—H10	0.9300	C4—H4A	0.9700
C9—C14	1.375 (4)	C3—C6	1.333 (3)
C9—C8	1.498 (3)	C3—C2	1.478 (4)
C14—C13	1.372 (4)	C2—C1	1.516 (4)
C14—H14	0.9300	C2—H2B	0.9700
C13—C12	1.391 (5)	C2—H2A	0.9700
C13—H13	0.9300	C1—H1B	0.9700
C12—C11	1.351 (5)	C1—H1A	0.9700
C12—H12	0.9300	C6—C7	1.427 (4)
C11—H11	0.9300	C6—H6	0.9300
C8—H8B	0.9700
C5—N1—C1	110.1 (2)	C4—C5—H5B	109.3
C5—N1—C8	110.5 (2)	N1—C5—H5A	109.3
C1—N1—C8	109.1 (2)	C4—C5—H5A	109.3
C11—C10—C9	120.9 (3)	H5B—C5—H5A	108.0
C11—C10—H10	119.6	C3—C4—C5	110.4 (2)
C9—C10—H10	119.6	C3—C4—H4B	109.6
C14—C9—C10	118.3 (3)	C5—C4—H4B	109.6
C14—C9—C8	121.1 (3)	C3—C4—H4A	109.6
C10—C9—C8	120.5 (3)	C5—C4—H4A	109.6
C13—C14—C9	121.2 (3)	H4B—C4—H4A	108.1
C13—C14—H14	119.4	C6—C3—C2	124.3 (3)
C9—C14—H14	119.4	C6—C3—C4	122.8 (3)
C14—C13—C12	118.9 (3)	C2—C3—C4	112.8 (2)
C14—C13—H13	120.6	C3—C2—C1	109.6 (2)
C12—C13—H13	120.6	C3—C2—H2B	109.8
C11—C12—C13	119.8 (4)	C1—C2—H2B	109.8
C11—C12—H12	120.1	C3—C2—H2A	109.8
C13—C12—H12	120.1	C1—C2—H2A	109.8
C12—C11—C10	120.8 (4)	H2B—C2—H2A	108.2
C12—C11—H11	119.6	N1—C1—C2	111.5 (2)
C10—C11—H11	119.6	N1—C1—H1B	109.3
N1—C8—C9	113.9 (2)	C2—C1—H1B	109.3
N1—C8—H8B	108.8	N1—C1—H1A	109.3
C9—C8—H8B	108.8	C2—C1—H1A	109.3
N1—C8—H8A	108.8	H1B—C1—H1A	108.0
C9—C8—H8A	108.8	C3—C6—C7	122.3 (3)
H8B—C8—H8A	107.7	C3—C6—H6	118.8
N1—C5—C4	111.5 (2)	C7—C6—H6	118.8
N1—C5—H5B	109.3	N2—C7—C6	179.8 (4)
C11—C10—C9—C14	0.6 (4)	C8—N1—C5—C4	−178.9 (2)
C11—C10—C9—C8	178.3 (3)	N1—C5—C4—C3	54.6 (3)
C10—C9—C14—C13	−0.6 (4)	C5—C4—C3—C6	124.6 (3)
C8—C9—C14—C13	−178.3 (3)	C5—C4—C3—C2	−52.7 (3)
C9—C14—C13—C12	0.1 (5)	C6—C3—C2—C1	−123.7 (3)
C14—C13—C12—C11	0.4 (5)	C4—C3—C2—C1	53.6 (3)
C13—C12—C11—C10	−0.4 (6)	C5—N1—C1—C2	59.8 (3)
C9—C10—C11—C12	−0.1 (5)	C8—N1—C1—C2	−178.8 (2)
C5—N1—C8—C9	−69.6 (3)	C3—C2—C1—N1	−56.9 (3)
C1—N1—C8—C9	169.2 (2)	C2—C3—C6—C7	−1.8 (5)
C14—C9—C8—N1	−67.6 (3)	C4—C3—C6—C7	−178.7 (3)
C10—C9—C8—N1	114.8 (3)	C3—C6—C7—N2	−81 (100)
C1—N1—C5—C4	−58.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N2^i	0.93	2.61	3.524 (5)	167

Symmetry code: (i) x−1, y, z+1.