1'-Benzylspiro-[chromene-2,4'-piperi-dine]-4-carbonitrile.

In the title compound, C(21)H(20)N(2)O, the piperidine ring adopts a chair conformation while the pyran ring adopts a screw-boat conformation. The piperidine ring forms dihedral angles of 65.75 (3) and 67.79 (5)° with the chroman and methyl-substituted benzene rings, respectively. The crystal structure features weak C-H⋯π and π-π [centroid-centroid distance = 3.8098 (8) Å] inter-actions.

Related literature

For the biological activity of piperidine­carbonitrile derivatives, see: Cardellicchio et al. (2010 ▶); Huang et al. (2008 ▶); Kumar et al. (2010 ▶); Arbiser et al. (2007 ▶). For uses of piperidine­carbonitrile derivatives, see: Barth et al. (2005 ▶); Vicente (2001 ▶); Terasaki et al. (2003 ▶). For industrial applications, see: Eller et al. (2002 ▶). For puckering prameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C21H20N2O

M = 316.39

Monoclinic,

a = 15.1666 (9) Å

b = 10.0472 (6) Å

c = 12.4360 (8) Å

β = 113.931 (2)°

V = 1732.11 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.974, T max = 0.981

24973 measured reflections

6238 independent reflections

3363 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.152

S = 1.01

6238 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLUTON (Spek, 2009) ▶; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035568/gw2123sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035568/gw2123Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035568/gw2123Isup3.cml

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

C21H20N2O	F(000) = 672
Mr = 316.39	Dx = 1.213 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6238 reflections
a = 15.1666 (9) Å	θ = 2.7–29.4°
b = 10.0472 (6) Å	µ = 0.08 mm−1
c = 12.4360 (8) Å	T = 298 K
β = 113.931 (2)°	Block, colourless
V = 1732.11 (18) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII diffractometer	6238 independent reflections
Radiation source: fine-focus sealed tube	3363 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 32.8°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −23→22
Tmin = 0.974, Tmax = 0.981	k = −15→15
24973 measured reflections	l = −18→17

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0684P)2 + 0.085P] where P = (Fo2 + 2Fc2)/3
6238 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.17 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
O1	0.20929 (5)	0.90059 (8)	0.08396 (8)	0.0525 (2)
N1	−0.11382 (9)	0.61311 (13)	−0.09299 (14)	0.0841 (4)
N2	0.43051 (7)	0.73556 (11)	0.14770 (9)	0.0543 (3)
C1	0.22110 (8)	0.76526 (11)	0.05117 (10)	0.0458 (3)
C2	0.13926 (8)	0.92304 (11)	0.12528 (10)	0.0460 (3)
C3	0.15085 (9)	1.02973 (13)	0.19913 (11)	0.0579 (3)
H3	0.2068	1.0808	0.2243	0.070*
C4	0.07830 (11)	1.06010 (15)	0.23549 (12)	0.0686 (4)
H4	0.0859	1.1318	0.2858	0.082*
C5	−0.00460 (10)	0.98619 (15)	0.19857 (12)	0.0675 (4)
H5	−0.0529	1.0080	0.2235	0.081*
C6	−0.01627 (9)	0.87965 (13)	0.12457 (12)	0.0578 (3)
H6	−0.0727	0.8297	0.0996	0.069*
C7	0.05550 (8)	0.84568 (11)	0.08656 (10)	0.0460 (3)
C8	0.04828 (8)	0.73709 (11)	0.00511 (11)	0.0495 (3)
C9	0.12497 (8)	0.70138 (12)	−0.01467 (11)	0.0516 (3)
H9	0.1187	0.6359	−0.0701	0.062*
C10	0.27778 (9)	0.68420 (13)	0.16113 (11)	0.0540 (3)
H10A	0.2448	0.6875	0.2135	0.065*
H10B	0.2797	0.5920	0.1391	0.065*
C11	0.37980 (9)	0.73457 (15)	0.22566 (11)	0.0600 (3)
H11A	0.3784	0.8239	0.2544	0.072*
H11B	0.4140	0.6778	0.2929	0.072*
C12	0.38213 (8)	0.82572 (14)	0.04959 (11)	0.0562 (3)
H12A	0.4177	0.8293	0.0001	0.067*
H12B	0.3809	0.9146	0.0794	0.067*
C13	0.27973 (8)	0.77961 (13)	−0.02271 (10)	0.0515 (3)
H13A	0.2816	0.6946	−0.0587	0.062*
H13B	0.2482	0.8432	−0.0853	0.062*
C14	0.53183 (9)	0.77325 (17)	0.21193 (13)	0.0705 (4)
H14A	0.5590	0.7223	0.2843	0.085*
H14B	0.5352	0.8667	0.2329	0.085*
C15	0.59135 (8)	0.75002 (13)	0.14180 (12)	0.0566 (3)
C16	0.58601 (8)	0.63042 (14)	0.08502 (12)	0.0605 (3)
H16	0.5452	0.5641	0.0903	0.073*
C17	0.63989 (9)	0.60737 (15)	0.02078 (13)	0.0671 (4)
H17	0.6346	0.5264	−0.0176	0.081*
C18	0.70137 (9)	0.70297 (17)	0.01293 (14)	0.0722 (4)
H18	0.7380	0.6872	−0.0303	0.087*
C19	0.70834 (10)	0.82101 (18)	0.06891 (18)	0.0856 (5)
H19	0.7501	0.8862	0.0640	0.103*
C20	0.65394 (10)	0.84503 (15)	0.13306 (16)	0.0792 (5)
H20	0.6595	0.9264	0.1709	0.095*
C21	−0.04213 (9)	0.66841 (13)	−0.05118 (13)	0.0603 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0519 (4)	0.0463 (5)	0.0652 (6)	−0.0025 (3)	0.0299 (4)	−0.0075 (4)
N1	0.0619 (7)	0.0730 (8)	0.1129 (11)	−0.0153 (6)	0.0308 (7)	−0.0042 (8)
N2	0.0463 (5)	0.0737 (7)	0.0408 (6)	0.0046 (4)	0.0154 (4)	−0.0039 (5)
C1	0.0492 (5)	0.0463 (6)	0.0452 (6)	0.0024 (4)	0.0225 (5)	−0.0040 (5)
C2	0.0491 (5)	0.0444 (6)	0.0453 (6)	0.0069 (5)	0.0200 (5)	0.0035 (5)
C3	0.0613 (7)	0.0534 (7)	0.0541 (8)	0.0061 (6)	0.0183 (6)	−0.0061 (6)
C4	0.0829 (9)	0.0674 (9)	0.0556 (8)	0.0221 (7)	0.0281 (7)	−0.0051 (7)
C5	0.0751 (9)	0.0775 (9)	0.0617 (9)	0.0274 (7)	0.0399 (7)	0.0133 (7)
C6	0.0576 (6)	0.0607 (8)	0.0627 (8)	0.0106 (6)	0.0323 (6)	0.0167 (6)
C7	0.0500 (5)	0.0427 (6)	0.0473 (7)	0.0063 (4)	0.0219 (5)	0.0094 (5)
C8	0.0505 (6)	0.0436 (6)	0.0535 (7)	−0.0026 (5)	0.0203 (5)	0.0046 (5)
C9	0.0550 (6)	0.0467 (6)	0.0524 (7)	−0.0021 (5)	0.0211 (5)	−0.0069 (5)
C10	0.0611 (7)	0.0600 (7)	0.0474 (7)	0.0074 (5)	0.0286 (6)	0.0056 (6)
C11	0.0629 (7)	0.0780 (9)	0.0389 (7)	0.0091 (6)	0.0203 (6)	0.0025 (6)
C12	0.0528 (6)	0.0717 (8)	0.0490 (7)	0.0022 (6)	0.0257 (5)	0.0028 (6)
C13	0.0517 (6)	0.0646 (7)	0.0395 (6)	0.0074 (5)	0.0197 (5)	0.0039 (5)
C14	0.0525 (7)	0.0940 (11)	0.0560 (8)	−0.0006 (7)	0.0128 (6)	−0.0216 (8)
C15	0.0404 (5)	0.0647 (8)	0.0545 (8)	0.0012 (5)	0.0086 (5)	−0.0105 (6)
C16	0.0505 (6)	0.0618 (8)	0.0643 (9)	−0.0030 (6)	0.0181 (6)	−0.0072 (6)
C17	0.0575 (7)	0.0708 (9)	0.0673 (9)	0.0113 (6)	0.0196 (6)	−0.0095 (7)
C18	0.0485 (7)	0.0940 (11)	0.0735 (10)	0.0155 (7)	0.0240 (7)	0.0089 (8)
C19	0.0569 (8)	0.0800 (11)	0.1225 (15)	−0.0040 (7)	0.0391 (9)	0.0061 (10)
C20	0.0590 (7)	0.0624 (9)	0.1117 (13)	−0.0068 (6)	0.0298 (8)	−0.0195 (8)
C21	0.0557 (7)	0.0515 (7)	0.0740 (9)	−0.0034 (5)	0.0266 (6)	0.0010 (6)

O1—C2	1.3732 (12)	C10—H10A	0.9700
O1—C1	1.4512 (13)	C10—H10B	0.9700
N1—C21	1.1413 (16)	C11—H11A	0.9700
N2—C12	1.4565 (16)	C11—H11B	0.9700
N2—C11	1.4618 (14)	C12—C13	1.5173 (17)
N2—C14	1.4652 (16)	C12—H12A	0.9700
C1—C9	1.4965 (16)	C12—H12B	0.9700
C1—C13	1.5227 (14)	C13—H13A	0.9700
C1—C10	1.5227 (17)	C13—H13B	0.9700
C2—C3	1.3757 (16)	C14—C15	1.5063 (17)
C2—C7	1.3977 (16)	C14—H14A	0.9700
C3—C4	1.3827 (18)	C14—H14B	0.9700
C3—H3	0.9300	C15—C16	1.3793 (18)
C4—C5	1.369 (2)	C15—C20	1.3812 (19)
C4—H4	0.9300	C16—C17	1.3746 (18)
C5—C6	1.375 (2)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.369 (2)
C6—C7	1.3936 (15)	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.357 (2)
C7—C8	1.4623 (16)	C18—H18	0.9300
C8—C9	1.3319 (15)	C19—C20	1.382 (2)
C8—C21	1.4380 (17)	C19—H19	0.9300
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.5122 (18)
C2—O1—C1	117.47 (8)	C10—C11—H11A	109.5
C12—N2—C11	109.76 (9)	N2—C11—H11B	109.5
C12—N2—C14	110.89 (11)	C10—C11—H11B	109.5
C11—N2—C14	110.97 (10)	H11A—C11—H11B	108.1
O1—C1—C9	110.59 (8)	N2—C12—C13	110.69 (10)
O1—C1—C13	104.46 (9)	N2—C12—H12A	109.5
C9—C1—C13	112.85 (10)	C13—C12—H12A	109.5
O1—C1—C10	109.75 (9)	N2—C12—H12B	109.5
C9—C1—C10	109.38 (9)	C13—C12—H12B	109.5
C13—C1—C10	109.72 (9)	H12A—C12—H12B	108.1
O1—C2—C3	117.97 (10)	C12—C13—C1	112.29 (9)
O1—C2—C7	120.84 (10)	C12—C13—H13A	109.1
C3—C2—C7	121.02 (10)	C1—C13—H13A	109.1
C2—C3—C4	119.16 (12)	C12—C13—H13B	109.1
C2—C3—H3	120.4	C1—C13—H13B	109.1
C4—C3—H3	120.4	H13A—C13—H13B	107.9
C5—C4—C3	120.99 (13)	N2—C14—C15	112.75 (10)
C5—C4—H4	119.5	N2—C14—H14A	109.0
C3—C4—H4	119.5	C15—C14—H14A	109.0
C4—C5—C6	119.86 (11)	N2—C14—H14B	109.0
C4—C5—H5	120.1	C15—C14—H14B	109.0
C6—C5—H5	120.1	H14A—C14—H14B	107.8
C5—C6—C7	120.75 (12)	C16—C15—C20	117.47 (12)
C5—C6—H6	119.6	C16—C15—C14	120.45 (12)
C7—C6—H6	119.6	C20—C15—C14	122.07 (13)
C6—C7—C2	118.22 (11)	C17—C16—C15	121.26 (13)
C6—C7—C8	124.64 (11)	C17—C16—H16	119.4
C2—C7—C8	117.11 (9)	C15—C16—H16	119.4
C9—C8—C21	120.83 (11)	C18—C17—C16	120.38 (14)
C9—C8—C7	120.22 (10)	C18—C17—H17	119.8
C21—C8—C7	118.94 (10)	C16—C17—H17	119.8
C8—C9—C1	120.88 (11)	C19—C18—C17	119.33 (13)
C8—C9—H9	119.6	C19—C18—H18	120.3
C1—C9—H9	119.6	C17—C18—H18	120.3
C11—C10—C1	112.40 (10)	C18—C19—C20	120.53 (14)
C11—C10—H10A	109.1	C18—C19—H19	119.7
C1—C10—H10A	109.1	C20—C19—H19	119.7
C11—C10—H10B	109.1	C15—C20—C19	121.00 (14)
C1—C10—H10B	109.1	C15—C20—H20	119.5
H10A—C10—H10B	107.9	C19—C20—H20	119.5
N2—C11—C10	110.53 (10)	N1—C21—C8	178.19 (16)
N2—C11—H11A	109.5
C2—O1—C1—C9	42.04 (13)	C9—C1—C10—C11	174.04 (9)
C2—O1—C1—C13	163.72 (9)	C13—C1—C10—C11	49.76 (13)
C2—O1—C1—C10	−78.72 (11)	C12—N2—C11—C10	61.96 (14)
C1—O1—C2—C3	154.00 (11)	C14—N2—C11—C10	−175.13 (11)
C1—O1—C2—C7	−30.59 (14)	C1—C10—C11—N2	−56.68 (14)
O1—C2—C3—C4	175.57 (11)	C11—N2—C12—C13	−61.80 (13)
C7—C2—C3—C4	0.17 (18)	C14—N2—C12—C13	175.24 (9)
C2—C3—C4—C5	−0.4 (2)	N2—C12—C13—C1	56.38 (13)
C3—C4—C5—C6	0.3 (2)	O1—C1—C13—C12	68.12 (12)
C4—C5—C6—C7	0.06 (19)	C9—C1—C13—C12	−171.70 (10)
C5—C6—C7—C2	−0.26 (17)	C10—C1—C13—C12	−49.46 (13)
C5—C6—C7—C8	−177.93 (11)	C12—N2—C14—C15	−68.92 (15)
O1—C2—C7—C6	−175.12 (10)	C11—N2—C14—C15	168.82 (12)
C3—C2—C7—C6	0.15 (17)	N2—C14—C15—C16	−48.09 (18)
O1—C2—C7—C8	2.72 (15)	N2—C14—C15—C20	132.97 (15)
C3—C2—C7—C8	177.99 (11)	C20—C15—C16—C17	−0.9 (2)
C6—C7—C8—C9	−171.55 (12)	C14—C15—C16—C17	−179.90 (12)
C2—C7—C8—C9	10.76 (17)	C15—C16—C17—C18	0.8 (2)
C6—C7—C8—C21	7.31 (18)	C16—C17—C18—C19	−0.2 (2)
C2—C7—C8—C21	−170.39 (11)	C17—C18—C19—C20	−0.1 (2)
C21—C8—C9—C1	−174.98 (11)	C16—C15—C20—C19	0.5 (2)
C7—C8—C9—C1	3.85 (18)	C14—C15—C20—C19	179.50 (14)
O1—C1—C9—C8	−29.20 (16)	C18—C19—C20—C15	0.0 (3)
C13—C1—C9—C8	−145.79 (12)	C9—C8—C21—N1	122 (5)
C10—C1—C9—C8	91.78 (13)	C7—C8—C21—N1	−57 (5)
O1—C1—C10—C11	−64.47 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1i	0.93	2.95	3.7587 (15)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1i	0.93	2.95	3.7587 (15)	146

Symmetry code: (i) .