Crystal structure of 2-(2,4-diphenyl-3-aza­bicyclo­[3.3.1]nonan-9-yl­idene)aceto­nitrile

Priya, K.; Saravanan, K.; Kabilan, S.; Selvanayagam, S.

doi:10.1107/S2056989015017740

organic compounds

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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o792-o793

doi:10.1107/S2056989015017740

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Crystal structure of 2-(2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene)acetonitrile

K. Priya,^a K. Saravanan,^a S. Kabilan ^a ^* and S. Selvanayagam ^b

^aDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, India, and ^bPG & Research Department of Physics, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: profskabilan@gmail.com

Edited by V. V. Chernyshev, Moscow State University, Russia (Received 12 September 2015; accepted 21 September 2015; online 26 September 2015)

In the title 3-azabicyclononane derivative, C₂₂H₂₂N₂, both the fused piperidine and cyclohexane rings adopt a chair conformation. The phenyl rings attached to the central azabicylononane 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.

Keywords: crystal structure; 3-azabicyclononane derivatives; chair conformation.

CCDC reference: 1426330

1. 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 ).

2. Experimental

2.1. Crystal data

C₂₂H₂₂N₂
M_r = 314.41
Triclinic, $[P \overline 1]$
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.131
S = 1.05
3814 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −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.

Supporting information

CCDC reference: 1426330

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2056989015017740/cv5495sup1.cif

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

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

checkCIF report

Chemical context top

Nitrile derivatives received considerable interest since they have been used in biological field as well as in optical fields (Silver et al., 1967). Alkenyl nitriles are unique structural units and versatile building blocks in organic synthesis for natural products, pharmaceuticals, agricultural chemicals, and dyes (Fleming & Wang, 2003; Miller & Manson,2001; Fatiadi, 1983). Hence, the synthesis and stereochemistry of 3-azabicyclononan-9-ones are under intensive study (Parthiban et al., 2008a, b, c, d, e). In continuation of our work with 3-azabicyclononane derivatives, we have undertaken the crystal structure determination of the title compound, and the results are presented here.

Structural commentary top

The molecular structure of the title compound is shown in Fig. 1. The bond length C22—N2 of 1.146 (2) Å confirms the triple bond character. Two phenyl rings attached to the 3-azabiclononane fragment form a dihedral angle of 23.7 (1)°. The piperidine (N1/C1—C5) and cyclohexane (C2—C4/C20/C19/C18) rings adopt chair conformation. This is confirmed by the puckering parameters q₂ = 0.044 (1) Å, q₃ = 0.598 (1) Å, Q_T = 0.600 (1) Å, φ = -156.7 (4)° for piperidine ring, and q₂ = 0.122 (1) Å, q₃ = -0.556 (1) Å, Q_T = 0.569 (1) Å, φ = -128.0 (1)° for cyclohexane ring. In the piperidine ring , atoms N1 and C3 deviate at 0.639 (1) and -0.705 (1) Å, respectively, from the least-squares plane formed by the remaining four atoms, whereas in cyclohexane ring, atoms C19 and C3 deviate at 0.562 (1) and -0.721 (1) Å, respectively, from the least-squares plane formed by the remaining four atoms.

Supramolecular features top

The crystal packing is stabilized by van der Waals forces only, since the amino group is not involved in any hydrogen-bonding interactions.

Synthesis and crystallization top

To a solution of the 2, 4-diphenyl-3-azabicyclo [3.3.1] nonan-9-one (500 mg, 1.72 mmol) in THF (5 mL), LiOH (212 mg, 3.516mmol) and diethylcyanomethyl phosphonate (364g, 1.4063mmol) was added. The reaction mixture was stirred at for 3 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with ethyl acetate (45 mL). The organic layer was washed with water (10 mL X 3) and dried over Na₂SO₄. The filtrate was concentrated and the crude product mass was purified by column-chromatography over silica-gel (100–200 mesh) using petroleum ether and diethyl ether (5-10%) as eluent to give a colorless solid. This solid was recrystallized in ethyl acetate to yield a colourless crystals of the title compound.

Refinement top

Atom H1N was located from a difference Fourier map and refined with a bond length restraint of 0.90 (2) Å. The remaining H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93-0.98 Å, and U_iso(H) = 1.5U_eq (C) for methyl H and U_iso(H) = 1.2U_eq(C) for all other H atoms.

Related literature top

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).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with atom labelling. Displacement ellipsoids are drawn at the 40% probability level.

2-{2,4-Diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene}acetonitrile top

Crystal data top

C₂₂H₂₂N₂	Z = 2
M_r = 314.41	F(000) = 336
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	R_int = 0.034
Radiation source: fine-focus sealed tube	θ_max = 27.2°, θ_min = 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 top

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(F_o²) + (0.0623P)² + 0.0228P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3814 reflections	Δρ_max = 0.13 e Å⁻³
221 parameters	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₂H₂₂N₂	γ = 84.469 (4)°
M_r = 314.41	V = 888.00 (9) Å³
Triclinic, P1	Z = 2
a = 7.9672 (5) Å	Mo Kα radiation
b = 8.3129 (5) Å	µ = 0.07 mm⁻¹
c = 13.6069 (8) Å	T = 296 K
α = 89.607 (4)°	0.23 × 0.21 × 0.19 mm
β = 81.886 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2375 reflections with I > 2σ(I)
14326 measured reflections	R_int = 0.034
3814 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.13 e Å⁻³
3814 reflections	Δρ_min = −0.16 e Å⁻³
221 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₂H₂₂N₂
M_r	314.41
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.9672 (5), 8.3129 (5), 13.6069 (8)
α, β, γ (°)	89.607 (4), 81.886 (4), 84.469 (4)
V (Å³)	888.00 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.23 × 0.21 × 0.19

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14326, 3814, 2375
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.643

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.131, 1.05
No. of reflections	3814
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.16

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), SHELXL2014/7 (Sheldrick, 2015) and PLATON (Spek, 2009).

Acknowledgements

KP is thankful to the UGC, New Delhi, for the award of a UGC–BSR–RFSMS Fellowship. The authors thank the Department of Biotechnology (DBT&NEC), New Delhi, for financial support, and the IIT - Guwahathi for the data collection.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fatiadi, A. J. (1983). In Preparation and Synthetic Applications of Cyano Compounds in Triple bonded functional groups. Vol. 2, edited by S. Patai & Z. Rappaport, pp. 1057–1303. Chichester: John Wiley & Sons, Ltd. Google Scholar
Fleming, F. F. & Wang, Q. (2003). Chem. Rev. 103, 2035–2078. CrossRef PubMed CAS Google Scholar
Miller, J. S. & Manson, J. L. (2001). Acc. Chem. Res. 34, 563–570. Web of Science CrossRef PubMed CAS Google Scholar
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Parthiban, P., Thirumurugan, K., Ramkumar, V., Pazhamalai, S. & Jeong, Y. T. (2008e). Acta Cryst. E64, o1708–o1709. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Silver, R. F., Kerr, K. A., Frandsen, P. D., Kelley, S. J. & Holmes, H. L. (1967). Can. J. Chem. 45, 1001–1006. CrossRef CAS Google Scholar
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Volume 71| Part 10| October 2015| Pages o792-o793

doi:10.1107/S2056989015017740

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 2-(2,4-di­phenyl-3-aza­bi­cyclo­[3.3.1]nonan-9-yl­­idene)aceto­nitrile

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 2-(2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene)acetonitrile