(2S,4aR,3S,8aR,9R,10R)-1,4-Diallyl-2,3-diphenyl-perhydro-quinoxaline.

In the title compound, C(26)H(32)N(2), the cyclo-hexane and piperazine rings each adopt a chair conformation. Both phenyl rings and the two propen-3-yl residues are in equatorial positions. There are no C-H⋯N hydrogen bonds nor π-π inter-actions between the aromatic rings. The absolute configuration was assigned with reference to the starting material.

Related literature

For an olefin–n class="Chemical">copper (I) complex with high anisotropy, see: Ye et al. (2007 ▶). For examples of the structure of olefins, see: Bond & Davies (2001 ▶); Presenti et al. (2001 ▶); Wang & Ye (2008 ▶).

Experimental

Crystal data

C26H32N2

M = 372.54

Orthorhombic,

a = 6.509 (4) Å

b = 17.437 (10) Å

c = 19.757 (12) Å

V = 2242 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.06 mm−1

T = 293 (2) K

0.35 × 0.15 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.808, T max = 1.000 (expected range = 0.801–0.990)

22256 measured reflections

2923 independent reflections

2452 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.154

S = 1.13

2923 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808011276/bt2698sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011276/bt2698Isup2.hkl

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

C26H32N2	F000 = 808
Mr = 372.54	Dx = 1.101 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 15922 reflections
a = 6.509 (4) Å	θ = 3.3–27.5º
b = 17.437 (10) Å	µ = 0.06 mm−1
c = 19.757 (12) Å	T = 293 (2) K
V = 2242 (2) Å3	Block, colorless
Z = 4	0.35 × 0.15 × 0.15 mm

Rigaku SCXmini diffractometer	2923 independent reflections
Radiation source: fine-focus sealed tube	2452 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
Detector resolution: 13.6612 pixels mm-1	θmax = 27.4º
T = 293(2) K	θmin = 3.3º
ω scans	h = −8→8
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −22→22
Tmin = 0.809, Tmax = 1.000	l = −25→25
22256 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059	H-atom parameters constrained
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.0674P)2 + 0.2312P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
2923 reflections	Δρmax = 0.15 e Å−3
254 parameters	Δρmin = −0.13 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
C1	0.5826 (4)	0.80378 (13)	0.84675 (11)	0.0506 (5)
H1A	0.7233	0.8238	0.8463	0.061*
C2	0.5523 (5)	0.75694 (16)	0.91185 (12)	0.0647 (7)
H2A	0.4177	0.7331	0.9110	0.078*
H2B	0.6544	0.7165	0.9137	0.078*
C3	0.5705 (6)	0.80629 (17)	0.97458 (13)	0.0761 (8)
H3A	0.5417	0.7754	1.0143	0.091*
H3B	0.7101	0.8253	0.9784	0.091*
C4	0.4241 (6)	0.87304 (17)	0.97238 (12)	0.0745 (8)
H4A	0.4446	0.9049	1.0120	0.089*
H4B	0.2839	0.8542	0.9732	0.089*
C5	0.4569 (5)	0.92060 (15)	0.90914 (11)	0.0643 (7)
H5A	0.5932	0.9431	0.9102	0.077*
H5B	0.3576	0.9621	0.9081	0.077*
C6	0.4339 (4)	0.87160 (12)	0.84510 (11)	0.0486 (5)
H6A	0.2934	0.8515	0.8436	0.058*
C7	0.3422 (5)	0.98753 (13)	0.78078 (14)	0.0653 (7)
H7A	0.3672	1.0132	0.7380	0.078*
H7B	0.3879	1.0216	0.8165	0.078*
C8	0.1147 (5)	0.97599 (18)	0.78826 (18)	0.0834 (9)
H8A	0.0553	0.9367	0.7631	0.100*
C9	−0.0048 (7)	1.0156 (3)	0.8263 (2)	0.1171 (14)
H9A	0.0483	1.0554	0.8523	0.141*
H9B	−0.1444	1.0045	0.8279	0.141*
C10	0.4402 (4)	0.86967 (12)	0.72229 (11)	0.0483 (5)
H10A	0.2982	0.8509	0.7218	0.058*
C11	0.4779 (4)	0.91552 (13)	0.65788 (11)	0.0533 (6)
C12	0.3334 (5)	0.91742 (15)	0.60669 (13)	0.0693 (8)
H12A	0.2095	0.8915	0.6120	0.083*
C13	0.3722 (7)	0.95790 (18)	0.54713 (15)	0.0914 (11)
H13A	0.2743	0.9585	0.5129	0.110*
C14	0.5517 (7)	0.9965 (2)	0.53880 (15)	0.0981 (12)
H14A	0.5765	1.0233	0.4990	0.118*
C15	0.6952 (6)	0.9957 (2)	0.58882 (17)	0.0956 (11)
H15A	0.8185	1.0219	0.5830	0.115*
C16	0.6586 (5)	0.95579 (16)	0.64889 (14)	0.0734 (8)
H16A	0.7567	0.9563	0.6831	0.088*
C17	0.5854 (4)	0.80049 (12)	0.72363 (11)	0.0494 (5)
H17A	0.7274	0.8192	0.7231	0.059*
C18	0.5511 (4)	0.75131 (14)	0.66111 (11)	0.0541 (6)
C19	0.6996 (5)	0.74603 (15)	0.61113 (13)	0.0677 (7)
H19A	0.8235	0.7719	0.6165	0.081*
C20	0.6668 (6)	0.70288 (18)	0.55319 (15)	0.0857 (10)
H20A	0.7678	0.7002	0.5200	0.103*
C21	0.4855 (6)	0.66430 (17)	0.54495 (15)	0.0826 (10)
H21A	0.4637	0.6352	0.5062	0.099*
C22	0.3358 (6)	0.66848 (16)	0.59373 (14)	0.0763 (8)
H22A	0.2119	0.6428	0.5878	0.092*
C23	0.3702 (4)	0.71126 (15)	0.65195 (13)	0.0642 (7)
H23A	0.2696	0.7129	0.6853	0.077*
C24	0.6823 (5)	0.68533 (14)	0.78648 (14)	0.0677 (7)
H24A	0.6575	0.6576	0.7447	0.081*
H24B	0.6373	0.6528	0.8234	0.081*
C25	0.9103 (5)	0.6977 (2)	0.79341 (19)	0.0882 (10)
H25A	0.9648	0.7397	0.7705	0.106*
C26	1.0331 (7)	0.6584 (3)	0.8261 (2)	0.1236 (16)
H26A	0.9870	0.6158	0.8499	0.148*
H26B	1.1716	0.6714	0.8269	0.148*
N1	0.4696 (3)	0.91737 (10)	0.78298 (9)	0.0510 (4)
N2	0.5531 (3)	0.75566 (10)	0.78624 (9)	0.0512 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0577 (13)	0.0487 (11)	0.0453 (11)	0.0009 (11)	−0.0019 (11)	0.0009 (9)
C2	0.0857 (18)	0.0610 (15)	0.0474 (12)	0.0109 (15)	−0.0022 (13)	0.0088 (11)
C3	0.102 (2)	0.0804 (18)	0.0453 (13)	0.0067 (19)	−0.0094 (15)	0.0070 (13)
C4	0.108 (2)	0.0775 (17)	0.0380 (11)	0.0065 (18)	−0.0012 (14)	−0.0055 (12)
C5	0.0890 (19)	0.0562 (14)	0.0477 (13)	0.0034 (14)	−0.0046 (13)	−0.0067 (11)
C6	0.0582 (13)	0.0467 (11)	0.0409 (11)	0.0014 (11)	−0.0041 (10)	−0.0008 (9)
C7	0.096 (2)	0.0444 (11)	0.0551 (13)	0.0100 (12)	−0.0002 (15)	0.0012 (11)
C8	0.089 (2)	0.0738 (17)	0.088 (2)	0.0259 (17)	−0.0153 (19)	−0.0051 (17)
C9	0.103 (3)	0.118 (3)	0.130 (3)	0.024 (3)	0.021 (3)	−0.012 (3)
C10	0.0579 (13)	0.0453 (11)	0.0419 (11)	−0.0045 (10)	−0.0003 (11)	0.0008 (9)
C11	0.0703 (15)	0.0473 (12)	0.0422 (11)	−0.0025 (12)	−0.0015 (11)	0.0024 (9)
C12	0.088 (2)	0.0602 (15)	0.0600 (15)	−0.0094 (15)	−0.0194 (14)	0.0080 (12)
C13	0.138 (3)	0.0806 (19)	0.0553 (16)	−0.014 (2)	−0.0286 (19)	0.0168 (15)
C14	0.155 (4)	0.085 (2)	0.0537 (16)	−0.026 (3)	−0.002 (2)	0.0203 (16)
C15	0.113 (3)	0.098 (2)	0.075 (2)	−0.038 (2)	0.012 (2)	0.0172 (18)
C16	0.0829 (19)	0.0798 (18)	0.0574 (14)	−0.0230 (16)	−0.0063 (15)	0.0153 (14)
C17	0.0553 (12)	0.0473 (11)	0.0457 (11)	−0.0027 (10)	0.0035 (11)	0.0010 (9)
C18	0.0682 (15)	0.0476 (12)	0.0464 (12)	0.0014 (12)	0.0053 (11)	−0.0016 (10)
C19	0.0761 (18)	0.0638 (15)	0.0630 (15)	−0.0032 (15)	0.0167 (13)	−0.0039 (13)
C20	0.113 (3)	0.085 (2)	0.0590 (16)	−0.006 (2)	0.0291 (18)	−0.0160 (15)
C21	0.119 (3)	0.0755 (19)	0.0527 (15)	0.002 (2)	0.0028 (17)	−0.0179 (14)
C22	0.090 (2)	0.0706 (17)	0.0681 (17)	−0.0135 (16)	−0.0041 (17)	−0.0106 (14)
C23	0.0728 (16)	0.0665 (15)	0.0534 (13)	−0.0082 (14)	0.0096 (13)	−0.0093 (12)
C24	0.097 (2)	0.0477 (12)	0.0581 (14)	0.0146 (13)	0.0004 (16)	0.0027 (11)
C25	0.084 (2)	0.0784 (19)	0.102 (2)	0.0273 (18)	0.0133 (19)	0.0080 (19)
C26	0.107 (3)	0.137 (4)	0.127 (4)	0.027 (3)	−0.026 (3)	0.007 (3)
N1	0.0688 (12)	0.0407 (9)	0.0434 (9)	0.0014 (8)	−0.0006 (10)	0.0024 (8)
N2	0.0653 (11)	0.0411 (9)	0.0474 (10)	0.0034 (8)	0.0014 (10)	0.0016 (8)

C1—N2	1.473 (3)	C12—C13	1.395 (4)
C1—C6	1.528 (3)	C12—H12A	0.9300
C1—C2	1.536 (3)	C13—C14	1.358 (6)
C1—H1A	0.9800	C13—H13A	0.9300
C2—C3	1.514 (4)	C14—C15	1.360 (5)
C2—H2A	0.9700	C14—H14A	0.9300
C2—H2B	0.9700	C15—C16	1.396 (4)
C3—C4	1.505 (4)	C15—H15A	0.9300
C3—H3A	0.9700	C16—H16A	0.9300
C3—H3B	0.9700	C17—N2	1.478 (3)
C4—C5	1.515 (4)	C17—C18	1.520 (3)
C4—H4A	0.9700	C17—H17A	0.9800
C4—H4B	0.9700	C18—C23	1.381 (4)
C5—C6	1.534 (3)	C18—C19	1.385 (4)
C5—H5A	0.9700	C19—C20	1.386 (4)
C5—H5B	0.9700	C19—H19A	0.9300
C6—N1	1.482 (3)	C20—C21	1.368 (5)
C6—H6A	0.9800	C20—H20A	0.9300
C7—N1	1.479 (3)	C21—C22	1.373 (5)
C7—C8	1.501 (5)	C21—H21A	0.9300
C7—H7A	0.9700	C22—C23	1.389 (4)
C7—H7B	0.9700	C22—H22A	0.9300
C8—C9	1.284 (5)	C23—H23A	0.9300
C8—H8A	0.9300	C24—N2	1.487 (3)
C9—H9A	0.9300	C24—C25	1.506 (5)
C9—H9B	0.9300	C24—H24A	0.9700
C10—N1	1.472 (3)	C24—H24B	0.9700
C10—C11	1.523 (3)	C25—C26	1.235 (5)
C10—C17	1.533 (3)	C25—H25A	0.9300
C10—H10A	0.9800	C26—H26A	0.9300
C11—C12	1.381 (4)	C26—H26B	0.9300
C11—C16	1.381 (4)
N2—C1—C6	109.94 (18)	C11—C12—C13	120.4 (3)
N2—C1—C2	111.09 (18)	C11—C12—H12A	119.8
C6—C1—C2	110.4 (2)	C13—C12—H12A	119.8
N2—C1—H1A	108.5	C14—C13—C12	120.5 (3)
C6—C1—H1A	108.5	C14—C13—H13A	119.7
C2—C1—H1A	108.5	C12—C13—H13A	119.7
C3—C2—C1	111.9 (2)	C13—C14—C15	119.9 (3)
C3—C2—H2A	109.2	C13—C14—H14A	120.1
C1—C2—H2A	109.2	C15—C14—H14A	120.1
C3—C2—H2B	109.2	C14—C15—C16	120.3 (3)
C1—C2—H2B	109.2	C14—C15—H15A	119.8
H2A—C2—H2B	107.9	C16—C15—H15A	119.8
C4—C3—C2	111.5 (2)	C11—C16—C15	120.5 (3)
C4—C3—H3A	109.3	C11—C16—H16A	119.7
C2—C3—H3A	109.3	C15—C16—H16A	119.7
C4—C3—H3B	109.3	N2—C17—C18	111.13 (17)
C2—C3—H3B	109.3	N2—C17—C10	110.05 (18)
H3A—C3—H3B	108.0	C18—C17—C10	109.82 (19)
C3—C4—C5	111.0 (2)	N2—C17—H17A	108.6
C3—C4—H4A	109.4	C18—C17—H17A	108.6
C5—C4—H4A	109.4	C10—C17—H17A	108.6
C3—C4—H4B	109.4	C23—C18—C19	117.9 (2)
C5—C4—H4B	109.4	C23—C18—C17	121.1 (2)
H4A—C4—H4B	108.0	C19—C18—C17	120.9 (2)
C4—C5—C6	111.2 (2)	C18—C19—C20	121.2 (3)
C4—C5—H5A	109.4	C18—C19—H19A	119.4
C6—C5—H5A	109.4	C20—C19—H19A	119.4
C4—C5—H5B	109.4	C21—C20—C19	119.9 (3)
C6—C5—H5B	109.4	C21—C20—H20A	120.1
H5A—C5—H5B	108.0	C19—C20—H20A	120.1
N1—C6—C1	109.56 (19)	C20—C21—C22	120.2 (3)
N1—C6—C5	111.58 (19)	C20—C21—H21A	119.9
C1—C6—C5	110.58 (19)	C22—C21—H21A	119.9
N1—C6—H6A	108.3	C21—C22—C23	119.7 (3)
C1—C6—H6A	108.3	C21—C22—H22A	120.2
C5—C6—H6A	108.3	C23—C22—H22A	120.2
N1—C7—C8	116.1 (2)	C18—C23—C22	121.2 (3)
N1—C7—H7A	108.3	C18—C23—H23A	119.4
C8—C7—H7A	108.3	C22—C23—H23A	119.4
N1—C7—H7B	108.3	N2—C24—C25	116.1 (2)
C8—C7—H7B	108.3	N2—C24—H24A	108.3
H7A—C7—H7B	107.4	C25—C24—H24A	108.3
C9—C8—C7	125.7 (4)	N2—C24—H24B	108.3
C9—C8—H8A	117.2	C25—C24—H24B	108.3
C7—C8—H8A	117.2	H24A—C24—H24B	107.4
C8—C9—H9A	120.0	C26—C25—C24	127.2 (4)
C8—C9—H9B	120.0	C26—C25—H25A	116.4
H9A—C9—H9B	120.0	C24—C25—H25A	116.4
N1—C10—C11	111.29 (17)	C25—C26—H26A	120.0
N1—C10—C17	110.49 (18)	C25—C26—H26B	120.0
C11—C10—C17	109.16 (18)	H26A—C26—H26B	120.0
N1—C10—H10A	108.6	C10—N1—C7	111.74 (19)
C11—C10—H10A	108.6	C10—N1—C6	110.48 (16)
C17—C10—H10A	108.6	C7—N1—C6	112.43 (19)
C12—C11—C16	118.3 (2)	C1—N2—C17	111.06 (16)
C12—C11—C10	121.0 (2)	C1—N2—C24	113.17 (19)
C16—C11—C10	120.8 (2)	C17—N2—C24	110.99 (19)
C11—C10—C17—C18	−58.0 (2)