4-(3,4-Dihydro-β-carbolin-1-yl)pyrimidin-2-amine.

The mol-ecule of accanthomine A, C(15)H(13)N(5), is approximately planar, with the indolyl fused-ring and the pyrimidyl ring being twisted by 31.7 (1)° The amino group of the five-membered ring is an intramolecular hydrogen-bond donor to a nitro-gen acceptor of the pyrimide ring. The amino group of the pyrimide ring is a hydrogen-bond donor to the N atoms of adjacent mol-ecules. These hydrogen-bonding inter-actions give rise to a layered network with a 4.8(2) topology.

Related literature

The β-carboline fragment is found in the crystal structures of two compounds that show selective CDK4-cycli D1 inhibitory activity; see: García et al. (2006 ▶). For related compounds, see: Costa et al. (2006 ▶); Kobayashi et al. (1995 ▶).

Experimental

Crystal data

C15H13N5

M = 263.30

Monoclinic,

a = 11.4758 (2) Å

b = 12.6095 (2) Å

c = 8.9241 (2) Å

β = 102.116 (1)°

V = 1262.59 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 120 K

0.45 × 0.35 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

11840 measured reflections

2905 independent reflections

2485 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.02

2905 reflections

193 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX (Dolomanov et al., 2003 ▶) and X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900600X/hg2480sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900600X/hg2480Isup2.hkl

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

C15H13N5	F(000) = 552
Mr = 263.30	Dx = 1.385 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4559 reflections
a = 11.4758 (2) Å	θ = 2.4–28.3°
b = 12.6095 (2) Å	µ = 0.09 mm−1
c = 8.9241 (2) Å	T = 120 K
β = 102.116 (1)°	Irregular block, light brown
V = 1262.59 (4) Å3	0.45 × 0.35 × 0.15 mm
Z = 4

Bruker SMART APEX diffractometer	2485 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 27.5°, θmin = 1.8°
ω scans	h = −14→14
11840 measured reflections	k = −16→16
2905 independent reflections	l = −11→11

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.3611P] where P = (Fo2 + 2Fc2)/3
2905 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.26 e Å−3
3 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.50153 (18)	0.76301 (16)	0.7128 (2)	0.0209 (4)
N2	0.55480 (17)	0.65191 (15)	0.9213 (2)	0.0187 (4)
N3	0.60199 (16)	0.61005 (14)	0.6777 (2)	0.0165 (4)
N4	0.73723 (17)	0.59739 (15)	0.4478 (2)	0.0180 (4)
C1	0.55292 (19)	0.67210 (17)	0.7718 (2)	0.0163 (4)
C2	0.6123 (2)	0.56393 (18)	0.9781 (3)	0.0194 (5)
H2	0.6172	0.5480	1.0833	0.023*
C3	0.6649 (2)	0.49480 (17)	0.8924 (3)	0.0187 (5)
H3	0.7049	0.4325	0.9356	0.022*
C4	0.65609 (18)	0.52161 (17)	0.7390 (2)	0.0159 (4)
C5	0.70796 (18)	0.45156 (17)	0.6351 (2)	0.0162 (4)
C6	0.7651 (2)	0.28242 (17)	0.5636 (3)	0.0199 (5)
H6A	0.6977	0.2605	0.4809	0.024*
H6B	0.7970	0.2176	0.6203	0.024*
C7	0.8626 (2)	0.32896 (17)	0.4896 (3)	0.0185 (5)
H7A	0.9393	0.3309	0.5650	0.022*
H7B	0.8728	0.2843	0.4020	0.022*
C8	0.82678 (19)	0.43888 (17)	0.4355 (2)	0.0165 (4)
C9	0.75008 (19)	0.49495 (17)	0.5047 (2)	0.0162 (4)
C10	0.86494 (19)	0.50915 (17)	0.3305 (2)	0.0168 (5)
C11	0.9446 (2)	0.50053 (18)	0.2302 (3)	0.0203 (5)
H11A	0.9863	0.4362	0.2233	0.024*
C12	0.9608 (2)	0.58717 (19)	0.1426 (3)	0.0227 (5)
H12A	1.0146	0.5823	0.0751	0.027*
C13	0.8991 (2)	0.68278 (19)	0.1512 (3)	0.0218 (5)
H13	0.9111	0.7406	0.0879	0.026*
C14	0.8217 (2)	0.69440 (18)	0.2493 (3)	0.0202 (5)
H14	0.7809	0.7593	0.2554	0.024*
C15	0.80577 (19)	0.60715 (17)	0.3395 (2)	0.0173 (5)
N5	0.71831 (17)	0.35226 (14)	0.6694 (2)	0.0188 (4)
H11	0.503 (3)	0.778 (2)	0.616 (2)	0.030 (8)*
H12	0.448 (3)	0.796 (2)	0.759 (4)	0.031 (8)*
H4	0.686 (2)	0.643 (2)	0.472 (3)	0.031 (8)*

	U11	U22	U33	U12	U13	U23
N1	0.0250 (10)	0.0207 (10)	0.0199 (10)	0.0063 (8)	0.0115 (8)	0.0024 (7)
N2	0.0208 (9)	0.0199 (9)	0.0167 (9)	−0.0008 (7)	0.0067 (7)	−0.0013 (7)
N3	0.0172 (9)	0.0161 (9)	0.0179 (9)	−0.0004 (7)	0.0072 (7)	−0.0004 (7)
N4	0.0193 (9)	0.0169 (9)	0.0202 (9)	0.0031 (7)	0.0097 (7)	0.0028 (7)
C1	0.0152 (10)	0.0174 (10)	0.0175 (10)	−0.0027 (8)	0.0061 (8)	−0.0010 (8)
C2	0.0218 (11)	0.0208 (11)	0.0157 (10)	−0.0030 (9)	0.0043 (8)	0.0004 (8)
C3	0.0214 (11)	0.0159 (10)	0.0192 (11)	−0.0006 (8)	0.0050 (9)	0.0020 (8)
C4	0.0142 (9)	0.0153 (10)	0.0191 (11)	−0.0032 (8)	0.0057 (8)	−0.0005 (8)
C5	0.0145 (9)	0.0166 (10)	0.0178 (10)	−0.0009 (8)	0.0040 (8)	0.0002 (8)
C6	0.0237 (11)	0.0151 (10)	0.0217 (11)	−0.0001 (8)	0.0065 (9)	−0.0018 (8)
C7	0.0197 (10)	0.0176 (10)	0.0187 (10)	0.0019 (8)	0.0055 (8)	−0.0023 (8)
C8	0.0163 (10)	0.0171 (10)	0.0160 (10)	−0.0005 (8)	0.0036 (8)	−0.0015 (8)
C9	0.0162 (10)	0.0155 (10)	0.0175 (10)	−0.0006 (8)	0.0045 (8)	0.0001 (8)
C10	0.0164 (10)	0.0188 (10)	0.0154 (10)	−0.0006 (8)	0.0035 (8)	−0.0012 (8)
C11	0.0203 (11)	0.0226 (11)	0.0195 (11)	0.0000 (9)	0.0077 (9)	−0.0041 (8)
C12	0.0219 (11)	0.0289 (12)	0.0196 (11)	−0.0024 (9)	0.0095 (9)	−0.0021 (9)
C13	0.0213 (11)	0.0261 (12)	0.0186 (11)	−0.0029 (9)	0.0054 (9)	0.0040 (9)
C14	0.0187 (10)	0.0210 (11)	0.0214 (11)	0.0019 (9)	0.0053 (9)	0.0032 (9)
C15	0.0154 (10)	0.0205 (11)	0.0165 (10)	−0.0002 (8)	0.0046 (8)	−0.0006 (8)
N5	0.0204 (9)	0.0160 (9)	0.0209 (9)	−0.0001 (7)	0.0068 (7)	−0.0009 (7)

N1—C1	1.345 (3)	C6—C7	1.531 (3)
N1—H11	0.894 (17)	C6—H6A	0.9900
N1—H12	0.91 (3)	C6—H6B	0.9900
N2—C2	1.335 (3)	C7—C8	1.497 (3)
N2—C1	1.354 (3)	C7—H7A	0.9900
N3—C4	1.336 (3)	C7—H7B	0.9900
N3—C1	1.354 (3)	C8—C9	1.373 (3)
N4—C15	1.374 (3)	C8—C10	1.424 (3)
N4—C9	1.384 (3)	C10—C11	1.411 (3)
N4—H4	0.883 (17)	C10—C15	1.420 (3)
C2—C3	1.380 (3)	C11—C12	1.379 (3)
C2—H2	0.9500	C11—H11A	0.9500
C3—C4	1.393 (3)	C12—C13	1.408 (3)
C3—H3	0.9500	C12—H12A	0.9500
C4—C5	1.492 (3)	C13—C14	1.380 (3)
C5—N5	1.288 (3)	C13—H13	0.9500
C5—C9	1.457 (3)	C14—C15	1.398 (3)
C6—N5	1.472 (3)	C14—H14	0.9500
C1—N1—H11	117.6 (19)	C8—C7—H7A	110.0
C1—N1—H12	120.0 (19)	C6—C7—H7A	110.0
H11—N1—H12	120 (3)	C8—C7—H7B	110.0
C2—N2—C1	115.78 (18)	C6—C7—H7B	110.0
C4—N3—C1	116.49 (18)	H7A—C7—H7B	108.4
C15—N4—C9	108.00 (17)	C9—C8—C10	106.88 (19)
C15—N4—H4	128 (2)	C9—C8—C7	119.37 (19)
C9—N4—H4	123 (2)	C10—C8—C7	133.41 (19)
N1—C1—N2	117.46 (19)	C8—C9—N4	110.16 (18)
N1—C1—N3	117.05 (19)	C8—C9—C5	121.2 (2)
N2—C1—N3	125.5 (2)	N4—C9—C5	127.99 (19)
N2—C2—C3	123.6 (2)	C11—C10—C15	119.0 (2)
N2—C2—H2	118.2	C11—C10—C8	134.3 (2)
C3—C2—H2	118.2	C15—C10—C8	106.69 (18)
C2—C3—C4	116.2 (2)	C12—C11—C10	118.7 (2)
C2—C3—H3	121.9	C12—C11—H11A	120.6
C4—C3—H3	121.9	C10—C11—H11A	120.6
N3—C4—C3	122.46 (19)	C11—C12—C13	121.2 (2)
N3—C4—C5	116.83 (18)	C11—C12—H12A	119.4
C3—C4—C5	120.71 (19)	C13—C12—H12A	119.4
N5—C5—C9	121.66 (19)	C14—C13—C12	121.6 (2)
N5—C5—C4	117.19 (19)	C14—C13—H13	119.2
C9—C5—C4	121.09 (19)	C12—C13—H13	119.2
N5—C6—C7	116.45 (18)	C13—C14—C15	117.5 (2)
N5—C6—H6A	108.2	C13—C14—H14	121.3
C7—C6—H6A	108.2	C15—C14—H14	121.3
N5—C6—H6B	108.2	N4—C15—C14	129.7 (2)
C7—C6—H6B	108.2	N4—C15—C10	108.25 (18)
H6A—C6—H6B	107.3	C14—C15—C10	122.0 (2)
C8—C7—C6	108.57 (17)	C5—N5—C6	117.20 (18)
C2—N2—C1—N1	−176.44 (19)	C4—C5—C9—C8	161.4 (2)
C2—N2—C1—N3	1.3 (3)	N5—C5—C9—N4	174.8 (2)
C4—N3—C1—N1	177.94 (19)	C4—C5—C9—N4	−8.1 (3)
C4—N3—C1—N2	0.2 (3)	C9—C8—C10—C11	177.9 (2)
C1—N2—C2—C3	−1.5 (3)	C7—C8—C10—C11	4.9 (4)
N2—C2—C3—C4	0.4 (3)	C9—C8—C10—C15	−1.1 (2)
C1—N3—C4—C3	−1.5 (3)	C7—C8—C10—C15	−174.0 (2)
C1—N3—C4—C5	178.65 (18)	C15—C10—C11—C12	−1.1 (3)
C2—C3—C4—N3	1.3 (3)	C8—C10—C11—C12	−179.9 (2)
C2—C3—C4—C5	−178.92 (19)	C10—C11—C12—C13	−0.3 (3)
N3—C4—C5—N5	−154.0 (2)	C11—C12—C13—C14	1.2 (4)
C3—C4—C5—N5	26.2 (3)	C12—C13—C14—C15	−0.6 (3)
N3—C4—C5—C9	28.7 (3)	C9—N4—C15—C14	179.5 (2)
C3—C4—C5—C9	−151.1 (2)	C9—N4—C15—C10	−1.2 (2)
N5—C6—C7—C8	−44.9 (3)	C13—C14—C15—N4	178.4 (2)
C6—C7—C8—C9	25.0 (3)	C13—C14—C15—C10	−0.9 (3)
C6—C7—C8—C10	−162.7 (2)	C11—C10—C15—N4	−177.72 (19)
C10—C8—C9—N4	0.4 (3)	C8—C10—C15—N4	1.4 (2)
C7—C8—C9—N4	174.49 (18)	C11—C10—C15—C14	1.7 (3)
C10—C8—C9—C5	−170.84 (19)	C8—C10—C15—C14	−179.2 (2)
C7—C8—C9—C5	3.3 (3)	C9—C5—N5—C6	−5.1 (3)
C15—N4—C9—C8	0.5 (3)	C4—C5—N5—C6	177.67 (18)
C15—N4—C9—C5	171.0 (2)	C7—C6—N5—C5	36.6 (3)
N5—C5—C9—C8	−15.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···N2i	0.89 (2)	2.14 (2)	2.994 (3)	161 (3)
N1—H12···N5ii	0.91 (3)	2.25 (3)	3.138 (3)	165 (3)
N4—H4···N3	0.88 (2)	2.29 (3)	2.825 (3)	119 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯N2i	0.89 (2)	2.14 (2)	2.994 (3)	161 (3)
N1—H12⋯N5ii	0.91 (3)	2.25 (3)	3.138 (3)	165 (3)
N4—H4⋯N3	0.88 (2)	2.29 (3)	2.825 (3)	119 (2)

Symmetry codes: (i) ; (ii) .