Crystal structure of 2-(2,4-diphenyl-3-aza-bicyclo-[3.3.1]nonan-9-yl-idene)aceto-nitrile.

In the title 3-aza-bicyclo-nonane derivative, C22H22N2, both the fused piperidine and cyclo-hexane rings adopt a chair conformation. The phenyl rings attached to the central aza-bicylononane fragment in an equatorial orientation are inclined to each other at 23.7 (1)°. The amino group is not involved in any hydrogen bonding, so the crystal packing is stabilized only by van der Waals forces.

Related literature

For the biological activities of 3-aza­bicyclo­nonane derivatives, see: Silver et al. (1967 ▸); Fleming & Wang (2003 ▸); Miller & Manson (2001 ▸); Fatiadi (1983 ▸). For related structures, see: Parthiban et al. (2008a ▸,b ▸,c ▸,d ▸,e ▸).

Experimental

Crystal data

C22H22N2

M = 314.41

Triclinic,

a = 7.9672 (5) Å

b = 8.3129 (5) Å

c = 13.6069 (8) Å

α = 89.607 (4)°

β = 81.886 (4)°

γ = 84.469 (4)°

V = 888.00 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.23 × 0.21 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

14326 measured reflections

3814 independent reflections

2375 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.131

S = 1.05

3814 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2001 ▸); cell refinement: SAINT (Bruker, 2001 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL2014/7 and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015017740/cv5495sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017740/cv5495Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015017740/cv5495Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015017740/cv5495fig1.tif

The mol­ecular structure of the title compound with atom labelling. Displacement ellipsoids are drawn at the 40% probability level.

CCDC reference: 1426330

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H22N2	Z = 2
Mr = 314.41	F(000) = 336
Triclinic, P1	Dx = 1.176 Mg m−3
a = 7.9672 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3129 (5) Å	Cell parameters from 9878 reflections
c = 13.6069 (8) Å	θ = 2.3–27.2°
α = 89.607 (4)°	µ = 0.07 mm−1
β = 81.886 (4)°	T = 296 K
γ = 84.469 (4)°	Block, colourless
V = 888.00 (9) Å3	0.23 × 0.21 × 0.19 mm

Bruker SMART APEX CCD area-detector diffractometer	Rint = 0.034
Radiation source: fine-focus sealed tube	θmax = 27.2°, θmin = 1.5°
ω scans	h = −10→10
14326 measured reflections	k = −9→10
3814 independent reflections	l = −17→17
2375 reflections with I > 2σ(I)

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0623P)2 + 0.0228P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3814 reflections	Δρmax = 0.13 e Å−3
221 parameters	Δρmin = −0.16 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
N1	0.30954 (14)	0.47358 (15)	0.20403 (9)	0.0491 (3)
H1N	0.3354 (19)	0.5473 (19)	0.1565 (12)	0.069 (5)*
N2	0.6722 (2)	0.17287 (19)	0.51383 (11)	0.0845 (5)
C1	0.21406 (17)	0.55407 (17)	0.29305 (10)	0.0494 (4)
H1A	0.2864	0.6291	0.3178	0.059*
C2	0.17259 (18)	0.42725 (18)	0.37503 (11)	0.0543 (4)
H2	0.1209	0.4846	0.4362	0.065*
C3	0.33678 (17)	0.33590 (17)	0.39353 (10)	0.0518 (4)
C4	0.42543 (17)	0.24949 (17)	0.30202 (10)	0.0503 (4)
H4	0.5326	0.1933	0.3171	0.060*
C5	0.46745 (16)	0.37958 (17)	0.22222 (10)	0.0465 (3)
H5	0.5395	0.4532	0.2485	0.056*
C6	0.05227 (17)	0.65065 (17)	0.27059 (11)	0.0511 (4)
C7	−0.0303 (2)	0.6131 (2)	0.19207 (13)	0.0661 (5)
H7	0.0167	0.5294	0.1487	0.079*
C8	−0.1827 (2)	0.6993 (2)	0.17744 (15)	0.0808 (5)
H8	−0.2375	0.6731	0.1246	0.097*
C9	−0.2528 (2)	0.8236 (2)	0.24123 (16)	0.0825 (6)
H9	−0.3550	0.8814	0.2314	0.099*
C10	−0.1720 (2)	0.8623 (2)	0.31933 (15)	0.0730 (5)
H10	−0.2195	0.9459	0.3626	0.088*
C11	−0.01988 (19)	0.77658 (18)	0.33353 (12)	0.0607 (4)
H11	0.0348	0.8039	0.3862	0.073*
C12	0.56488 (17)	0.30391 (16)	0.12778 (10)	0.0475 (3)
C13	0.48803 (19)	0.2693 (2)	0.04674 (11)	0.0614 (4)
H13	0.3721	0.2981	0.0478	0.074*
C14	0.5812 (2)	0.1923 (2)	−0.03620 (12)	0.0710 (5)
H14	0.5270	0.1690	−0.0899	0.085*
C15	0.7520 (2)	0.1501 (2)	−0.03997 (13)	0.0717 (5)
H15	0.8139	0.0983	−0.0959	0.086*
C16	0.8314 (2)	0.1848 (2)	0.03951 (14)	0.0772 (5)
H16	0.9478	0.1571	0.0375	0.093*
C17	0.73838 (18)	0.2608 (2)	0.12246 (12)	0.0660 (5)
H17	0.7933	0.2837	0.1759	0.079*
C18	0.05238 (18)	0.3031 (2)	0.35037 (12)	0.0643 (4)
H18A	0.0231	0.2383	0.4087	0.077*
H18B	−0.0520	0.3606	0.3343	0.077*
C19	0.12981 (19)	0.19133 (19)	0.26393 (12)	0.0634 (4)
H19A	0.1298	0.2507	0.2023	0.076*
H19B	0.0597	0.1028	0.2612	0.076*
C20	0.31190 (19)	0.12269 (17)	0.27312 (12)	0.0588 (4)
H20A	0.3635	0.0737	0.2102	0.071*
H20B	0.3080	0.0382	0.3227	0.071*
C21	0.39261 (19)	0.33330 (18)	0.48167 (11)	0.0575 (4)
H21	0.3278	0.3924	0.5339	0.069*
C22	0.5476 (2)	0.2435 (2)	0.49907 (11)	0.0613 (4)

	U11	U22	U33	U12	U13	U23
N1	0.0458 (7)	0.0516 (7)	0.0477 (7)	0.0043 (5)	−0.0046 (5)	0.0050 (6)
N2	0.0855 (11)	0.0958 (12)	0.0753 (10)	0.0097 (9)	−0.0348 (8)	0.0004 (9)
C1	0.0453 (8)	0.0515 (8)	0.0503 (9)	0.0025 (6)	−0.0075 (6)	−0.0030 (7)
C2	0.0505 (8)	0.0635 (10)	0.0454 (8)	0.0066 (7)	−0.0029 (6)	−0.0003 (7)
C3	0.0515 (8)	0.0557 (9)	0.0477 (9)	−0.0010 (7)	−0.0084 (7)	0.0047 (7)
C4	0.0473 (8)	0.0552 (9)	0.0479 (8)	0.0069 (6)	−0.0127 (6)	0.0020 (7)
C5	0.0407 (7)	0.0513 (8)	0.0474 (8)	−0.0005 (6)	−0.0084 (6)	−0.0022 (7)
C6	0.0474 (8)	0.0488 (8)	0.0552 (9)	0.0015 (6)	−0.0043 (7)	0.0033 (7)
C7	0.0596 (10)	0.0666 (10)	0.0712 (11)	0.0116 (8)	−0.0180 (8)	−0.0069 (9)
C8	0.0714 (11)	0.0835 (13)	0.0895 (14)	0.0119 (9)	−0.0310 (10)	−0.0014 (11)
C9	0.0612 (11)	0.0734 (12)	0.1101 (16)	0.0195 (9)	−0.0200 (10)	0.0072 (11)
C10	0.0662 (11)	0.0580 (10)	0.0882 (13)	0.0135 (8)	−0.0014 (9)	−0.0027 (9)
C11	0.0609 (9)	0.0528 (9)	0.0658 (10)	0.0046 (7)	−0.0068 (8)	−0.0015 (8)
C12	0.0451 (8)	0.0486 (8)	0.0479 (8)	−0.0007 (6)	−0.0067 (6)	0.0008 (7)
C13	0.0540 (9)	0.0757 (11)	0.0533 (10)	0.0053 (8)	−0.0112 (7)	−0.0042 (8)
C14	0.0782 (12)	0.0826 (12)	0.0512 (10)	0.0030 (9)	−0.0127 (8)	−0.0090 (9)
C15	0.0770 (12)	0.0732 (11)	0.0576 (10)	0.0086 (9)	0.0052 (9)	−0.0101 (9)
C16	0.0508 (9)	0.0956 (14)	0.0791 (13)	0.0118 (9)	−0.0002 (9)	−0.0140 (11)
C17	0.0487 (9)	0.0839 (12)	0.0641 (11)	0.0048 (8)	−0.0100 (7)	−0.0135 (9)
C18	0.0487 (9)	0.0721 (11)	0.0706 (11)	−0.0041 (7)	−0.0051 (7)	0.0172 (9)
C19	0.0581 (9)	0.0599 (10)	0.0754 (11)	−0.0145 (7)	−0.0147 (8)	0.0076 (9)
C20	0.0652 (10)	0.0510 (9)	0.0601 (10)	−0.0017 (7)	−0.0112 (7)	0.0066 (8)
C21	0.0621 (9)	0.0621 (10)	0.0472 (9)	0.0014 (7)	−0.0094 (7)	0.0002 (7)
C22	0.0708 (11)	0.0681 (10)	0.0478 (9)	−0.0033 (8)	−0.0204 (8)	0.0011 (8)

N1—C1	1.4651 (17)	C10—C11	1.383 (2)
N1—C5	1.4665 (16)	C10—H10	0.9300
N1—H1N	0.904 (16)	C11—H11	0.9300
N2—C22	1.1461 (18)	C12—C13	1.379 (2)
C1—C6	1.5191 (18)	C12—C17	1.3860 (18)
C1—C2	1.553 (2)	C13—C14	1.385 (2)
C1—H1A	0.9800	C13—H13	0.9300
C2—C3	1.5000 (18)	C14—C15	1.365 (2)
C2—C18	1.543 (2)	C14—H14	0.9300
C2—H2	0.9800	C15—C16	1.373 (2)
C3—C21	1.3361 (19)	C15—H15	0.9300
C3—C4	1.4939 (19)	C16—C17	1.381 (2)
C4—C20	1.541 (2)	C16—H16	0.9300
C4—C5	1.5529 (19)	C17—H17	0.9300
C4—H4	0.9800	C18—C19	1.526 (2)
C5—C12	1.5116 (18)	C18—H18A	0.9700
C5—H5	0.9800	C18—H18B	0.9700
C6—C7	1.384 (2)	C19—C20	1.5286 (19)
C6—C11	1.385 (2)	C19—H19A	0.9700
C7—C8	1.388 (2)	C19—H19B	0.9700
C7—H7	0.9300	C20—H20A	0.9700
C8—C9	1.378 (2)	C20—H20B	0.9700
C8—H8	0.9300	C21—C22	1.428 (2)
C9—C10	1.373 (3)	C21—H21	0.9300
C9—H9	0.9300
C1—N1—C5	113.55 (11)	C11—C10—H10	120.1
C1—N1—H1N	110.1 (10)	C10—C11—C6	121.05 (16)
C5—N1—H1N	108.7 (9)	C10—C11—H11	119.5
N1—C1—C6	111.71 (11)	C6—C11—H11	119.5
N1—C1—C2	109.87 (11)	C13—C12—C17	117.63 (14)
C6—C1—C2	110.76 (11)	C13—C12—C5	123.02 (12)
N1—C1—H1A	108.1	C17—C12—C5	119.30 (12)
C6—C1—H1A	108.1	C12—C13—C14	120.89 (14)
C2—C1—H1A	108.1	C12—C13—H13	119.6
C3—C2—C18	107.86 (12)	C14—C13—H13	119.6
C3—C2—C1	108.18 (11)	C15—C14—C13	120.67 (15)
C18—C2—C1	115.18 (12)	C15—C14—H14	119.7
C3—C2—H2	108.5	C13—C14—H14	119.7
C18—C2—H2	108.5	C14—C15—C16	119.43 (15)
C1—C2—H2	108.5	C14—C15—H15	120.3
C21—C3—C4	125.54 (13)	C16—C15—H15	120.3
C21—C3—C2	123.15 (14)	C15—C16—C17	119.93 (15)
C4—C3—C2	111.31 (11)	C15—C16—H16	120.0
C3—C4—C20	108.48 (12)	C17—C16—H16	120.0
C3—C4—C5	107.33 (11)	C16—C17—C12	121.45 (15)
C20—C4—C5	115.21 (11)	C16—C17—H17	119.3
C3—C4—H4	108.6	C12—C17—H17	119.3
C20—C4—H4	108.6	C19—C18—C2	113.21 (12)
C5—C4—H4	108.6	C19—C18—H18A	108.9
N1—C5—C12	111.71 (11)	C2—C18—H18A	108.9
N1—C5—C4	109.50 (10)	C19—C18—H18B	108.9
C12—C5—C4	111.25 (11)	C2—C18—H18B	108.9
N1—C5—H5	108.1	H18A—C18—H18B	107.7
C12—C5—H5	108.1	C18—C19—C20	112.39 (13)
C4—C5—H5	108.1	C18—C19—H19A	109.1
C7—C6—C11	118.53 (14)	C20—C19—H19A	109.1
C7—C6—C1	122.50 (13)	C18—C19—H19B	109.1
C11—C6—C1	118.91 (13)	C20—C19—H19B	109.1
C6—C7—C8	120.54 (16)	H19A—C19—H19B	107.9
C6—C7—H7	119.7	C19—C20—C4	113.88 (12)
C8—C7—H7	119.7	C19—C20—H20A	108.8
C9—C8—C7	120.01 (17)	C4—C20—H20A	108.8
C9—C8—H8	120.0	C19—C20—H20B	108.8
C7—C8—H8	120.0	C4—C20—H20B	108.8
C10—C9—C8	120.03 (16)	H20A—C20—H20B	107.7
C10—C9—H9	120.0	C3—C21—C22	122.75 (14)
C8—C9—H9	120.0	C3—C21—H21	118.6
C9—C10—C11	119.84 (17)	C22—C21—H21	118.6
C9—C10—H10	120.1	N2—C22—C21	179.18 (18)
C5—N1—C1—C6	179.66 (11)	C6—C7—C8—C9	0.1 (3)
C5—N1—C1—C2	−57.00 (15)	C7—C8—C9—C10	0.0 (3)
N1—C1—C2—C3	55.94 (15)	C8—C9—C10—C11	0.3 (3)
C6—C1—C2—C3	179.83 (11)	C9—C10—C11—C6	−0.6 (3)
N1—C1—C2—C18	−64.80 (15)	C7—C6—C11—C10	0.7 (2)
C6—C1—C2—C18	59.09 (16)	C1—C6—C11—C10	−176.43 (14)
C18—C2—C3—C21	−115.00 (16)	N1—C5—C12—C13	−25.14 (19)
C1—C2—C3—C21	119.81 (16)	C4—C5—C12—C13	97.57 (16)
C18—C2—C3—C4	64.47 (15)	N1—C5—C12—C17	157.44 (13)
C1—C2—C3—C4	−60.72 (15)	C4—C5—C12—C17	−79.85 (16)
C21—C3—C4—C20	116.21 (16)	C17—C12—C13—C14	0.8 (2)
C2—C3—C4—C20	−63.25 (14)	C5—C12—C13—C14	−176.61 (14)
C21—C3—C4—C5	−118.71 (15)	C12—C13—C14—C15	−0.6 (3)
C2—C3—C4—C5	61.83 (14)	C13—C14—C15—C16	0.0 (3)
C1—N1—C5—C12	−177.87 (11)	C14—C15—C16—C17	0.4 (3)
C1—N1—C5—C4	58.42 (15)	C15—C16—C17—C12	−0.1 (3)
C3—C4—C5—N1	−58.56 (14)	C13—C12—C17—C16	−0.5 (2)
C20—C4—C5—N1	62.36 (15)	C5—C12—C17—C16	177.05 (15)
C3—C4—C5—C12	177.47 (10)	C3—C2—C18—C19	−55.28 (16)
C20—C4—C5—C12	−61.61 (14)	C1—C2—C18—C19	65.64 (16)
N1—C1—C6—C7	25.8 (2)	C2—C18—C19—C20	46.74 (17)
C2—C1—C6—C7	−97.05 (17)	C18—C19—C20—C4	−45.54 (17)
N1—C1—C6—C11	−157.20 (13)	C3—C4—C20—C19	52.91 (15)
C2—C1—C6—C11	79.97 (16)	C5—C4—C20—C19	−67.39 (16)
C11—C6—C7—C8	−0.5 (2)	C4—C3—C21—C22	−0.6 (2)
C1—C6—C7—C8	176.55 (14)	C2—C3—C21—C22	178.80 (14)