(S)-Perillaldehyde azine.

The C=N-N=C linkage [torsion angle -172.5 (2)°] in the title azine, C(20)H(28)N(2), adopts a trans conformation. The six-membered rings adopt sofa conformations.

Related literature

A previous study reported the oxime derivative of S-perillaldehyde; see Yuan et al. (2009 ▶). Only few crystal structures of azines have been reported, see: Berthou et al. (1970 ▶); Kim & Lee (2008 ▶); Marek et al. (1997 ▶); Rizal et al. (2008 ▶); Sanz et al. (1999 ▶).

Experimental

Crystal data

C20H28N2

M = 296.44

Monoclinic,

a = 8.8200 (5) Å

b = 9.7603 (6) Å

c = 10.1710 (6) Å

β = 94.970 (1)°

V = 872.29 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 173 K

0.48 × 0.46 × 0.21 mm

Data collection

Bruker SMART APEX diffractometer

7179 measured reflections

2013 independent reflections

1802 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.141

S = 1.12

2013 reflections

201 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004071/bt5184sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004071/bt5184Isup2.hkl

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

C20H28N2	F(000) = 324
Mr = 296.44	Dx = 1.129 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4048 reflections
a = 8.8200 (5) Å	θ = 2.3–27.2°
b = 9.7603 (6) Å	µ = 0.07 mm−1
c = 10.1710 (6) Å	T = 173 K
β = 94.970 (1)°	Block, yellow
V = 872.29 (9) Å3	0.48 × 0.46 × 0.21 mm
Z = 2

Bruker SMART APEX diffractometer	1802 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 27.2°, θmin = 2.0°
ω scans	h = −11→11
7179 measured reflections	k = −12→12
2013 independent reflections	l = −12→12

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.074P)2 + 0.242P] where P = (Fo2 + 2Fc2)/3
2013 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
N1	1.1573 (3)	0.4999 (3)	0.9681 (2)	0.0344 (5)
N2	1.2864 (3)	0.5570 (3)	1.0416 (2)	0.0340 (5)
C1	0.3418 (3)	0.5570 (4)	0.6676 (3)	0.0432 (7)
H1A	0.2556	0.5311	0.6053	0.065*
H1B	0.3581	0.6561	0.6631	0.065*
H1C	0.3200	0.5317	0.7573	0.065*
C2	0.4821 (3)	0.4836 (3)	0.6326 (3)	0.0335 (6)
C3	0.4827 (4)	0.4131 (4)	0.5213 (3)	0.0451 (8)
H3A	0.3933	0.4085	0.4623	0.054*
H3B	0.5725	0.3672	0.5006	0.054*
C4	0.6201 (3)	0.4954 (3)	0.7323 (3)	0.0303 (6)
H4	0.5881	0.4606	0.8182	0.036*
C5	0.6657 (4)	0.6461 (3)	0.7542 (3)	0.0403 (7)
H5A	0.6717	0.6907	0.6674	0.048*
H5B	0.5856	0.6933	0.7995	0.048*
C6	0.8147 (3)	0.6631 (3)	0.8341 (3)	0.0369 (6)
H6	0.8407	0.7518	0.8673	0.044*
C7	0.9134 (3)	0.5613 (3)	0.8618 (3)	0.0302 (6)
C8	0.8822 (3)	0.4179 (3)	0.8139 (3)	0.0373 (7)
H8A	0.8524	0.3612	0.8882	0.045*
H8B	0.9767	0.3785	0.7837	0.045*
C9	0.7568 (3)	0.4114 (3)	0.7014 (3)	0.0356 (6)
H9A	0.7962	0.4465	0.6196	0.043*
H9B	0.7255	0.3149	0.6860	0.043*
C10	1.0558 (3)	0.5917 (3)	0.9402 (3)	0.0325 (6)
H10	1.0739	0.6824	0.9716	0.039*
C11	1.3954 (3)	0.4699 (3)	1.0567 (3)	0.0321 (6)
H11	1.3816	0.3810	1.0195	0.038*
C12	1.5398 (3)	0.5041 (3)	1.1296 (3)	0.0302 (6)
C13	1.6523 (3)	0.4117 (3)	1.1373 (3)	0.0340 (6)
H13	1.6335	0.3259	1.0948	0.041*
C14	1.8062 (3)	0.4349 (3)	1.2089 (3)	0.0349 (6)
H14A	1.8814	0.4500	1.1436	0.042*
H14B	1.8370	0.3517	1.2603	0.042*
C15	1.8082 (3)	0.5578 (3)	1.3023 (3)	0.0318 (6)
H15	1.7472	0.5319	1.3769	0.038*
C16	1.7255 (3)	0.6772 (3)	1.2292 (3)	0.0370 (7)
H16A	1.7332	0.7600	1.2855	0.044*
H16B	1.7748	0.6974	1.1475	0.044*
C17	1.5580 (3)	0.6425 (3)	1.1939 (3)	0.0384 (7)
H17A	1.5035	0.6437	1.2750	0.046*
H17B	1.5116	0.7131	1.1331	0.046*
C18	1.9656 (3)	0.5985 (3)	1.3620 (3)	0.0342 (6)
C19	1.9691 (4)	0.7035 (4)	1.4708 (3)	0.0460 (8)
H19A	2.0750	0.7240	1.5018	0.069*
H19B	1.9160	0.6674	1.5442	0.069*
H19C	1.9186	0.7875	1.4373	0.069*
C20	2.0927 (3)	0.5473 (4)	1.3233 (3)	0.0407 (7)
H20A	2.1881	0.5766	1.3641	0.049*
H20B	2.0888	0.4812	1.2546	0.049*

	U11	U22	U33	U12	U13	U23
N1	0.0284 (11)	0.0386 (13)	0.0355 (12)	−0.0022 (11)	−0.0012 (9)	−0.0030 (11)
N2	0.0286 (12)	0.0386 (13)	0.0342 (11)	−0.0017 (11)	−0.0011 (9)	−0.0028 (11)
C1	0.0339 (15)	0.0515 (18)	0.0434 (15)	0.0057 (15)	−0.0007 (12)	−0.0029 (15)
C2	0.0291 (13)	0.0356 (15)	0.0352 (13)	−0.0007 (13)	−0.0007 (11)	0.0034 (12)
C3	0.0401 (16)	0.052 (2)	0.0420 (17)	0.0017 (16)	−0.0050 (13)	−0.0098 (16)
C4	0.0303 (13)	0.0304 (13)	0.0297 (12)	0.0008 (12)	−0.0003 (10)	−0.0007 (11)
C5	0.0366 (16)	0.0284 (14)	0.0547 (17)	0.0077 (13)	−0.0036 (13)	−0.0055 (14)
C6	0.0350 (15)	0.0281 (14)	0.0466 (15)	−0.0013 (12)	−0.0019 (12)	−0.0054 (13)
C7	0.0287 (13)	0.0328 (14)	0.0289 (12)	−0.0008 (12)	0.0010 (10)	−0.0031 (11)
C8	0.0349 (15)	0.0314 (15)	0.0438 (15)	0.0055 (13)	−0.0064 (12)	−0.0025 (14)
C9	0.0356 (14)	0.0275 (14)	0.0426 (15)	0.0031 (12)	−0.0031 (12)	−0.0060 (13)
C10	0.0316 (14)	0.0328 (15)	0.0334 (13)	−0.0029 (12)	0.0038 (11)	−0.0045 (11)
C11	0.0336 (14)	0.0330 (16)	0.0296 (13)	−0.0038 (12)	0.0029 (10)	0.0011 (11)
C12	0.0299 (13)	0.0320 (14)	0.0288 (12)	−0.0032 (12)	0.0037 (10)	0.0027 (11)
C13	0.0343 (14)	0.0320 (14)	0.0349 (13)	−0.0020 (13)	−0.0015 (11)	0.0011 (12)
C14	0.0309 (14)	0.0318 (15)	0.0411 (15)	0.0020 (12)	−0.0027 (11)	0.0006 (12)
C15	0.0290 (13)	0.0362 (15)	0.0302 (12)	−0.0040 (12)	0.0027 (10)	0.0031 (12)
C16	0.0342 (15)	0.0318 (15)	0.0434 (15)	−0.0035 (12)	−0.0054 (12)	−0.0012 (12)
C17	0.0335 (15)	0.0349 (16)	0.0451 (16)	0.0027 (13)	−0.0061 (12)	−0.0021 (14)
C18	0.0351 (15)	0.0372 (16)	0.0296 (13)	−0.0048 (12)	−0.0011 (11)	0.0054 (11)
C19	0.0404 (17)	0.059 (2)	0.0382 (16)	−0.0084 (16)	0.0010 (12)	−0.0103 (15)
C20	0.0319 (15)	0.0471 (18)	0.0416 (15)	−0.0016 (14)	−0.0048 (12)	0.0004 (15)

N1—C10	1.280 (4)	C10—H10	0.9500
N1—N2	1.421 (3)	C11—C12	1.456 (4)
N2—C11	1.282 (4)	C11—H11	0.9500
C1—C2	1.499 (4)	C12—C13	1.338 (4)
C1—H1A	0.9800	C12—C17	1.503 (4)
C1—H1B	0.9800	C13—C14	1.501 (4)
C1—H1C	0.9800	C13—H13	0.9500
C2—C3	1.325 (4)	C14—C15	1.529 (4)
C2—C4	1.519 (4)	C14—H14A	0.9900
C3—H3A	0.9500	C14—H14B	0.9900
C3—H3B	0.9500	C15—C18	1.519 (4)
C4—C9	1.513 (4)	C15—C16	1.533 (4)
C4—C5	1.537 (4)	C15—H15	1.0000
C4—H4	1.0000	C16—C17	1.528 (4)
C5—C6	1.493 (4)	C16—H16A	0.9900
C5—H5A	0.9900	C16—H16B	0.9900
C5—H5B	0.9900	C17—H17A	0.9900
C6—C7	1.335 (4)	C17—H17B	0.9900
C6—H6	0.9500	C18—C20	1.318 (4)
C7—C10	1.459 (4)	C18—C19	1.507 (4)
C7—C8	1.500 (4)	C19—H19A	0.9800
C8—C9	1.523 (4)	C19—H19B	0.9800
C8—H8A	0.9900	C19—H19C	0.9800
C8—H8B	0.9900	C20—H20A	0.9500
C9—H9A	0.9900	C20—H20B	0.9500
C9—H9B	0.9900
C10—N1—N2	110.8 (3)	C7—C10—H10	119.0
C11—N2—N1	111.2 (2)	N2—C11—C12	121.5 (3)
C2—C1—H1A	109.5	N2—C11—H11	119.3
C2—C1—H1B	109.5	C12—C11—H11	119.3
H1A—C1—H1B	109.5	C13—C12—C11	119.1 (3)
C2—C1—H1C	109.5	C13—C12—C17	122.0 (3)
H1A—C1—H1C	109.5	C11—C12—C17	118.9 (3)
H1B—C1—H1C	109.5	C12—C13—C14	124.2 (3)
C3—C2—C1	121.0 (3)	C12—C13—H13	117.9
C3—C2—C4	123.2 (3)	C14—C13—H13	117.9
C1—C2—C4	115.8 (3)	C13—C14—C15	112.4 (2)
C2—C3—H3A	120.0	C13—C14—H14A	109.1
C2—C3—H3B	120.0	C15—C14—H14A	109.1
H3A—C3—H3B	120.0	C13—C14—H14B	109.1
C9—C4—C2	115.3 (2)	C15—C14—H14B	109.1
C9—C4—C5	110.2 (2)	H14A—C14—H14B	107.9
C2—C4—C5	110.7 (2)	C18—C15—C14	114.5 (2)
C9—C4—H4	106.7	C18—C15—C16	112.0 (2)
C2—C4—H4	106.7	C14—C15—C16	108.4 (2)
C5—C4—H4	106.7	C18—C15—H15	107.2
C6—C5—C4	113.1 (2)	C14—C15—H15	107.2
C6—C5—H5A	108.9	C16—C15—H15	107.2
C4—C5—H5A	108.9	C17—C16—C15	110.8 (2)
C6—C5—H5B	108.9	C17—C16—H16A	109.5
C4—C5—H5B	108.9	C15—C16—H16A	109.5
H5A—C5—H5B	107.8	C17—C16—H16B	109.5
C7—C6—C5	124.0 (3)	C15—C16—H16B	109.5
C7—C6—H6	118.0	H16A—C16—H16B	108.1
C5—C6—H6	118.0	C12—C17—C16	111.4 (3)
C6—C7—C10	118.6 (3)	C12—C17—H17A	109.3
C6—C7—C8	121.9 (2)	C16—C17—H17A	109.3
C10—C7—C8	119.5 (3)	C12—C17—H17B	109.3
C7—C8—C9	112.5 (2)	C16—C17—H17B	109.3
C7—C8—H8A	109.1	H17A—C17—H17B	108.0
C9—C8—H8A	109.1	C20—C18—C19	120.9 (3)
C7—C8—H8B	109.1	C20—C18—C15	123.6 (3)
C9—C8—H8B	109.1	C19—C18—C15	115.6 (3)
H8A—C8—H8B	107.8	C18—C19—H19A	109.5
C4—C9—C8	111.2 (2)	C18—C19—H19B	109.5
C4—C9—H9A	109.4	H19A—C19—H19B	109.5
C8—C9—H9A	109.4	C18—C19—H19C	109.5
C4—C9—H9B	109.4	H19A—C19—H19C	109.5
C8—C9—H9B	109.4	H19B—C19—H19C	109.5
H9A—C9—H9B	108.0	C18—C20—H20A	120.0
N1—C10—C7	122.1 (3)	C18—C20—H20B	120.0
N1—C10—H10	119.0	H20A—C20—H20B	120.0
C10—N1—N2—C11	−172.5 (2)	N1—N2—C11—C12	−179.6 (2)
C3—C2—C4—C9	−4.6 (4)	N2—C11—C12—C13	−176.9 (3)
C1—C2—C4—C9	175.2 (3)	N2—C11—C12—C17	3.0 (4)
C3—C2—C4—C5	121.3 (4)	C11—C12—C13—C14	179.7 (2)
C1—C2—C4—C5	−58.9 (4)	C17—C12—C13—C14	−0.2 (4)
C9—C4—C5—C6	−42.0 (3)	C12—C13—C14—C15	15.4 (4)
C2—C4—C5—C6	−170.7 (2)	C13—C14—C15—C18	−171.5 (2)
C4—C5—C6—C7	12.8 (4)	C13—C14—C15—C16	−45.7 (3)
C5—C6—C7—C10	179.6 (3)	C18—C15—C16—C17	−168.8 (2)
C5—C6—C7—C8	−0.1 (5)	C14—C15—C16—C17	63.9 (3)
C6—C7—C8—C9	17.4 (4)	C13—C12—C17—C16	16.9 (4)
C10—C7—C8—C9	−162.3 (2)	C11—C12—C17—C16	−163.0 (2)
C2—C4—C9—C8	−173.8 (3)	C15—C16—C17—C12	−48.7 (3)
C5—C4—C9—C8	60.0 (3)	C14—C15—C18—C20	9.7 (4)
C7—C8—C9—C4	−47.3 (4)	C16—C15—C18—C20	−114.2 (3)
N2—N1—C10—C7	178.1 (2)	C14—C15—C18—C19	−170.4 (3)
C6—C7—C10—N1	−178.4 (3)	C16—C15—C18—C19	65.7 (3)
C8—C7—C10—N1	1.2 (4)