Evodiamide.

The title compound, C(19)H(21)N(3)O, was isolated from the fruits of Evodia rutaecarpa. The indole and benzene rings are both essentially planar with mean derivations of 0.0094 (4) Å and 0.0077 (3) Å, respectively. The dihedral angle between these two planes is 78.24 (9)°. The amide carbonyl plane is roughly parallel to the indole ring with a dihedral angle of 7.0 (2)°, but makes a dihedral angle of 82.9 (3)° with the benzene ring. Inter-molecular N-H⋯O hydrogen-bonding inter-actions involving the amino and carbonyl groups give rise to a three-dimensional network.

Related literature

For previous isolation of evodiamide, see: Shoji et al. (1988 ▶); Tang et al. (1997 ▶); Zuo et al. (2003 ▶). For the LC–MS analysis, see: Zhou et al. (2006 ▶). For the crystal structure of evodiamine, see: Fujii et al. (2000 ▶). For the biological activity of Evodia rutaecarpa and related alkaloids, see: Liao et al. (2011 ▶).

Experimental

Crystal data

C19H21N3O

M = 307.39

Triclinic,

a = 8.958 (2) Å

b = 9.886 (2) Å

c = 10.616 (2) Å

α = 84.076 (4)°

β = 76.276 (4)°

γ = 66.746 (3)°

V = 839.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 291 K

0.45 × 0.36 × 0.30 mm

Data collection

Bruker SMART CCD 1000 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.661, T max = 1.000

4931 measured reflections

3424 independent reflections

2149 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.146

S = 1.04

3424 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART and SAINT (Bruker, 1998 ▶); data reduction: XPREP in SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055553/vm2145sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055553/vm2145Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055553/vm2145Isup3.cml

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

C19H21N3O	Z = 2
Mr = 307.39	F(000) = 328
Triclinic, P1	Dx = 1.217 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.958 (2) Å	Cell parameters from 4931 reflections
b = 9.886 (2) Å	θ = 2.2–26.5°
c = 10.616 (2) Å	µ = 0.08 mm−1
α = 84.076 (4)°	T = 291 K
β = 76.276 (4)°	Prism, colorless
γ = 66.746 (3)°	0.45 × 0.36 × 0.30 mm
V = 839.0 (3) Å3

Bruker SMART CCD 1000 diffractometer	3424 independent reflections
Radiation source: fine-focus sealed tube	2149 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω scan	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→11
Tmin = 0.661, Tmax = 1.000	k = −10→12
4931 measured reflections	l = −13→9

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) = 0.146	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0649P)2 + 0.1581P] where P = (Fo2 + 2Fc2)/3
3424 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.22 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
N1	0.7904 (2)	−0.28425 (19)	0.26473 (18)	0.0509 (5)
H1A	0.8747	−0.3553	0.2853	0.069 (8)*
N2	0.2948 (2)	0.31488 (17)	0.37369 (17)	0.0437 (4)
N3	−0.0454 (2)	0.23860 (19)	0.48132 (17)	0.0485 (5)
H3A	0.0126	0.2686	0.5169	0.135 (14)*
O1	0.08389 (18)	0.52561 (15)	0.34402 (16)	0.0558 (4)
C1	0.7523 (3)	−0.1380 (2)	0.2787 (2)	0.0490 (5)
H1	0.8143	−0.1003	0.3127	0.059*
C2	0.6114 (2)	−0.0550 (2)	0.2362 (2)	0.0438 (5)
C3	0.5579 (2)	−0.1564 (2)	0.19235 (18)	0.0431 (5)
C4	0.6720 (3)	−0.2988 (2)	0.21239 (19)	0.0459 (5)
C5	0.6557 (3)	−0.4248 (3)	0.1821 (2)	0.0579 (6)
H5	0.7322	−0.5180	0.1966	0.070*
C6	0.5236 (4)	−0.4069 (3)	0.1305 (2)	0.0703 (7)
H6	0.5089	−0.4895	0.1104	0.084*
C7	0.4092 (3)	−0.2662 (3)	0.1069 (2)	0.0686 (7)
H7	0.3213	−0.2574	0.0701	0.082*
C8	0.4249 (3)	−0.1416 (3)	0.1372 (2)	0.0570 (6)
H8	0.3485	−0.0488	0.1213	0.068*
C9	0.5227 (3)	0.1091 (2)	0.2416 (2)	0.0494 (5)
H9A	0.4777	0.1441	0.1644	0.059*
H9B	0.6012	0.1537	0.2429	0.059*
C10	0.3823 (2)	0.1555 (2)	0.3612 (2)	0.0452 (5)
H10A	0.3030	0.1124	0.3580	0.054*
H10B	0.4276	0.1165	0.4377	0.054*
C11	0.3714 (3)	0.3946 (2)	0.4276 (2)	0.0586 (6)
H11A	0.3025	0.4977	0.4307	0.088*
H11B	0.4791	0.3800	0.3740	0.088*
H11C	0.3831	0.3585	0.5137	0.088*
C12	0.1543 (2)	0.3898 (2)	0.33301 (19)	0.0396 (5)
C13	0.0829 (2)	0.3066 (2)	0.27095 (19)	0.0405 (5)
C14	−0.0184 (2)	0.2372 (2)	0.34723 (19)	0.0405 (5)
C15	−0.0836 (3)	0.1641 (2)	0.2837 (2)	0.0500 (6)
H15	−0.1513	0.1177	0.3321	0.060*
C16	−0.0495 (3)	0.1595 (3)	0.1507 (2)	0.0603 (6)
H16	−0.0928	0.1085	0.1105	0.072*
C17	0.0476 (3)	0.2289 (3)	0.0761 (2)	0.0629 (7)
H17	0.0689	0.2268	−0.0140	0.076*
C18	0.1131 (3)	0.3022 (2)	0.1380 (2)	0.0530 (6)
H18	0.1791	0.3495	0.0885	0.064*
C19	−0.1698 (3)	0.1902 (2)	0.5620 (2)	0.0609 (6)
H19A	−0.2751	0.2438	0.5386	0.091*
H19B	−0.1791	0.2077	0.6514	0.091*
H19C	−0.1379	0.0869	0.5497	0.091*

	U11	U22	U33	U12	U13	U23
N1	0.0455 (10)	0.0397 (10)	0.0620 (12)	−0.0070 (8)	−0.0185 (9)	0.0013 (8)
N2	0.0400 (9)	0.0362 (9)	0.0556 (11)	−0.0119 (8)	−0.0160 (8)	−0.0015 (8)
N3	0.0515 (11)	0.0527 (11)	0.0452 (11)	−0.0260 (9)	−0.0070 (9)	0.0000 (8)
O1	0.0516 (9)	0.0349 (8)	0.0805 (11)	−0.0076 (7)	−0.0265 (8)	−0.0077 (7)
C1	0.0446 (12)	0.0448 (13)	0.0562 (14)	−0.0154 (10)	−0.0101 (10)	−0.0029 (10)
C2	0.0380 (11)	0.0406 (11)	0.0451 (12)	−0.0100 (9)	−0.0035 (9)	−0.0006 (9)
C3	0.0413 (11)	0.0475 (12)	0.0349 (11)	−0.0142 (10)	−0.0030 (9)	−0.0002 (9)
C4	0.0501 (12)	0.0459 (12)	0.0375 (11)	−0.0165 (10)	−0.0048 (9)	−0.0015 (9)
C5	0.0734 (17)	0.0495 (14)	0.0505 (14)	−0.0234 (12)	−0.0122 (12)	−0.0025 (10)
C6	0.100 (2)	0.0733 (18)	0.0512 (15)	−0.0477 (17)	−0.0130 (15)	−0.0067 (13)
C7	0.0757 (18)	0.095 (2)	0.0520 (15)	−0.0456 (17)	−0.0221 (13)	−0.0012 (14)
C8	0.0538 (14)	0.0681 (16)	0.0477 (13)	−0.0217 (12)	−0.0136 (11)	0.0051 (11)
C9	0.0430 (12)	0.0409 (12)	0.0588 (14)	−0.0131 (9)	−0.0083 (10)	0.0043 (10)
C10	0.0406 (11)	0.0371 (11)	0.0534 (13)	−0.0097 (9)	−0.0128 (10)	0.0043 (9)
C11	0.0540 (14)	0.0532 (14)	0.0775 (17)	−0.0210 (11)	−0.0279 (12)	−0.0047 (12)
C12	0.0385 (11)	0.0364 (11)	0.0428 (12)	−0.0135 (9)	−0.0083 (9)	−0.0009 (9)
C13	0.0375 (11)	0.0355 (11)	0.0448 (12)	−0.0097 (9)	−0.0076 (9)	−0.0049 (9)
C14	0.0381 (11)	0.0312 (10)	0.0483 (12)	−0.0086 (9)	−0.0093 (9)	−0.0028 (9)
C15	0.0497 (13)	0.0454 (12)	0.0596 (15)	−0.0228 (10)	−0.0095 (11)	−0.0078 (10)
C16	0.0615 (15)	0.0617 (15)	0.0640 (16)	−0.0237 (13)	−0.0178 (13)	−0.0171 (12)
C17	0.0641 (16)	0.0791 (17)	0.0457 (14)	−0.0256 (14)	−0.0105 (12)	−0.0124 (12)
C18	0.0523 (13)	0.0624 (14)	0.0456 (13)	−0.0253 (12)	−0.0060 (10)	−0.0029 (11)
C19	0.0628 (15)	0.0583 (15)	0.0599 (15)	−0.0287 (12)	−0.0008 (12)	0.0001 (11)

N1—C1	1.363 (3)	C8—H8	0.9300
N1—C4	1.368 (3)	C9—C10	1.521 (3)
N1—H1A	0.8600	C9—H9A	0.9700
N2—C12	1.332 (2)	C9—H9B	0.9700
N2—C11	1.458 (3)	C10—H10A	0.9700
N2—C10	1.461 (2)	C10—H10B	0.9700
N3—C14	1.387 (3)	C11—H11A	0.9600
N3—C19	1.445 (3)	C11—H11B	0.9600
N3—H3A	0.8600	C11—H11C	0.9600
O1—C12	1.242 (2)	C12—C13	1.500 (3)
C1—C2	1.359 (3)	C13—C18	1.374 (3)
C1—H1	0.9300	C13—C14	1.406 (3)
C2—C3	1.425 (3)	C14—C15	1.392 (3)
C2—C9	1.499 (3)	C15—C16	1.373 (3)
C3—C8	1.400 (3)	C15—H15	0.9300
C3—C4	1.406 (3)	C16—C17	1.374 (3)
C4—C5	1.386 (3)	C16—H16	0.9300
C5—C6	1.362 (3)	C17—C18	1.385 (3)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.404 (4)	C18—H18	0.9300
C6—H6	0.9300	C19—H19A	0.9600
C7—C8	1.372 (3)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C1—N1—C4	108.52 (18)	N2—C10—C9	113.61 (17)
C1—N1—H1A	125.7	N2—C10—H10A	108.8
C4—N1—H1A	125.7	C9—C10—H10A	108.8
C12—N2—C11	119.29 (17)	N2—C10—H10B	108.8
C12—N2—C10	123.18 (17)	C9—C10—H10B	108.8
C11—N2—C10	117.46 (16)	H10A—C10—H10B	107.7
C14—N3—C19	120.82 (18)	N2—C11—H11A	109.5
C14—N3—H3A	119.6	N2—C11—H11B	109.5
C19—N3—H3A	119.6	H11A—C11—H11B	109.5
C2—C1—N1	110.75 (19)	N2—C11—H11C	109.5
C2—C1—H1	124.6	H11A—C11—H11C	109.5
N1—C1—H1	124.6	H11B—C11—H11C	109.5
C1—C2—C3	106.02 (18)	O1—C12—N2	121.55 (18)
C1—C2—C9	127.5 (2)	O1—C12—C13	120.06 (17)
C3—C2—C9	126.38 (19)	N2—C12—C13	118.39 (17)
C8—C3—C4	118.6 (2)	C18—C13—C14	119.92 (19)
C8—C3—C2	134.2 (2)	C18—C13—C12	119.34 (18)
C4—C3—C2	107.22 (18)	C14—C13—C12	120.70 (17)
N1—C4—C5	130.0 (2)	N3—C14—C15	122.18 (19)
N1—C4—C3	107.49 (18)	N3—C14—C13	119.84 (18)
C5—C4—C3	122.5 (2)	C15—C14—C13	117.93 (19)
C6—C5—C4	117.5 (2)	C16—C15—C14	121.0 (2)
C6—C5—H5	121.2	C16—C15—H15	119.5
C4—C5—H5	121.2	C14—C15—H15	119.5
C5—C6—C7	121.4 (2)	C15—C16—C17	121.1 (2)
C5—C6—H6	119.3	C15—C16—H16	119.4
C7—C6—H6	119.3	C17—C16—H16	119.4
C8—C7—C6	121.1 (2)	C16—C17—C18	118.4 (2)
C8—C7—H7	119.4	C16—C17—H17	120.8
C6—C7—H7	119.4	C18—C17—H17	120.8
C7—C8—C3	118.9 (2)	C13—C18—C17	121.6 (2)
C7—C8—H8	120.6	C13—C18—H18	119.2
C3—C8—H8	120.6	C17—C18—H18	119.2
C2—C9—C10	111.22 (17)	N3—C19—H19A	109.5
C2—C9—H9A	109.4	N3—C19—H19B	109.5
C10—C9—H9A	109.4	H19A—C19—H19B	109.5
C2—C9—H9B	109.4	N3—C19—H19C	109.5
C10—C9—H9B	109.4	H19A—C19—H19C	109.5
H9A—C9—H9B	108.0	H19B—C19—H19C	109.5
C4—N1—C1—C2	−0.3 (2)	C11—N2—C10—C9	−80.9 (2)
N1—C1—C2—C3	−0.1 (2)	C2—C9—C10—N2	178.10 (17)
N1—C1—C2—C9	176.33 (19)	C11—N2—C12—O1	−2.5 (3)
C1—C2—C3—C8	−179.1 (2)	C10—N2—C12—O1	−179.33 (18)
C9—C2—C3—C8	4.4 (4)	C11—N2—C12—C13	176.58 (18)
C1—C2—C3—C4	0.5 (2)	C10—N2—C12—C13	−0.2 (3)
C9—C2—C3—C4	−176.03 (19)	O1—C12—C13—C18	81.0 (2)
C1—N1—C4—C5	−179.0 (2)	N2—C12—C13—C18	−98.1 (2)
C1—N1—C4—C3	0.6 (2)	O1—C12—C13—C14	−97.0 (2)
C8—C3—C4—N1	179.03 (18)	N2—C12—C13—C14	83.9 (2)
C2—C3—C4—N1	−0.7 (2)	C19—N3—C14—C15	−12.8 (3)
C8—C3—C4—C5	−1.4 (3)	C19—N3—C14—C13	169.64 (18)
C2—C3—C4—C5	178.93 (19)	C18—C13—C14—N3	178.39 (18)
N1—C4—C5—C6	179.8 (2)	C12—C13—C14—N3	−3.6 (3)
C3—C4—C5—C6	0.4 (3)	C18—C13—C14—C15	0.8 (3)
C4—C5—C6—C7	0.9 (4)	C12—C13—C14—C15	178.76 (17)
C5—C6—C7—C8	−1.1 (4)	N3—C14—C15—C16	−177.4 (2)
C6—C7—C8—C3	0.1 (3)	C13—C14—C15—C16	0.2 (3)
C4—C3—C8—C7	1.1 (3)	C14—C15—C16—C17	−1.1 (4)
C2—C3—C8—C7	−179.3 (2)	C15—C16—C17—C18	1.1 (4)
C1—C2—C9—C10	−95.3 (3)	C14—C13—C18—C17	−0.9 (3)
C3—C2—C9—C10	80.5 (3)	C12—C13—C18—C17	−178.9 (2)
C12—N2—C10—C9	95.9 (2)	C16—C17—C18—C13	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	1.99	2.824 (3)	164
N3—H3A···O1ii	0.86	2.38	2.991 (4)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	1.99	2.824 (3)	164
N3—H3A⋯O1ii	0.86	2.39	2.991 (4)	128

Symmetry codes: (i) ; (ii) .