Antalarmin.

In the mol-ecule of the title compund [systematic name: N-butyl-N-ethyl-2,5,6-trimethyl-7-(2,4,6-trimethyl-phen-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine], C(24)H(34)N(4), the pyrrolopy-rimidine ring system is nearly planar, its five- and six-membered rings forming a dihedral angle of 5.3 (2)°. The benzene ring is nearly orthogonal to the central ring system. The N atom carrying the ethyl and n-butyl groups is flattened pyramidal.

Related literature

For related literature, see: Allen (2002 ▶); Chorvat et al. (1999 ▶); Chu et al. (2007 ▶); Dieterich et al. (1997 ▶); Gross et al. (2005 ▶); Habib et al. (2000 ▶); Horn et al. (2008 ▶); Hsin et al. (2002 ▶); Banić Tomišić et al. (2001 ▶); Rivier & Vale (1983 ▶); Steckler & Holsboer (1999 ▶); Vale et al. (1981 ▶); Greiner et al. (2002 ▶).

Experimental

Crystal data

C24H34N4

M = 378.55

Triclinic,

a = 10.2656 (10) Å

b = 11.0655 (11) Å

c = 11.5029 (12) Å

α = 63.646 (6)°

β = 85.669 (6)°

γ = 73.036 (5)°

V = 1117.69 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 150 K

0.40 × 0.37 × 0.30 mm

Data collection

Nonius KappaCCD diffractometer with Oxford Cryostream

Absorption correction: none

35420 measured reflections

8550 independent reflections

6916 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.142

S = 1.03

8550 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997 ▶); data reduction: HKL (Otwinowski & Minor 1997 ▶) DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023775/pv2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023775/pv2088Isup2.hkl

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

C24H34N4	Z = 2
Mr = 378.55	F000 = 412
Triclinic, P1	Dx = 1.125 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.2656 (10) Å	Cell parameters from 7613 reflections
b = 11.0655 (11) Å	θ = 2.5–34.3º
c = 11.5029 (12) Å	µ = 0.07 mm−1
α = 63.646 (6)º	T = 150 K
β = 85.669 (6)º	Fragment, colorless
γ = 73.036 (5)º	0.40 × 0.37 × 0.30 mm
V = 1117.69 (19) Å3

Nonius KappaCCD diffractometer with Oxford Cryostream	6916 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Monochromator: graphite	θmax = 34.3º
T = 150 K	θmin = 2.6º
ω and φ scans	h = −15→16
Absorption correction: none	k = −17→16
35420 measured reflections	l = −17→17
8550 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0675P)2 + 0.2841P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.142	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.44 e Å−3
8550 reflections	Δρmin = −0.24 e Å−3
262 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (5)
Secondary atom site location: difference Fourier map

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	0.57024 (7)	0.44531 (8)	0.71728 (7)	0.02058 (14)
N2	0.63299 (7)	0.27413 (8)	0.63295 (7)	0.02111 (14)
N3	0.75731 (7)	0.51591 (8)	0.75233 (8)	0.02095 (14)
N4	0.85651 (8)	0.16323 (8)	0.60760 (8)	0.02270 (15)
C1	0.54248 (8)	0.36459 (9)	0.67003 (8)	0.02038 (15)
C2	0.76639 (8)	0.26219 (9)	0.64044 (8)	0.01867 (14)
C3	0.80944 (8)	0.35136 (8)	0.67783 (8)	0.01795 (14)
C4	0.93184 (8)	0.38865 (9)	0.68326 (8)	0.02052 (15)
C5	0.89619 (9)	0.48788 (9)	0.73001 (9)	0.02223 (16)
C6	0.70349 (8)	0.43622 (8)	0.71773 (8)	0.01811 (14)
C7	0.39518 (9)	0.37212 (11)	0.65875 (10)	0.02787 (19)
H7A	0.3624	0.4225	0.5670	0.042*
H7B	0.3409	0.4223	0.7063	0.042*
H7C	0.3861	0.2765	0.6957	0.042*
C8	1.06921 (9)	0.34405 (11)	0.63522 (10)	0.02737 (18)
H8A	1.1281	0.2617	0.7068	0.041*
H8B	1.1107	0.4215	0.6026	0.041*
H8C	1.0585	0.3198	0.5650	0.041*
C9	0.98058 (11)	0.56497 (12)	0.75378 (12)	0.0329 (2)
H9A	1.0761	0.5279	0.7389	0.049*
H9B	0.9737	0.5521	0.8438	0.049*
H9C	0.9474	0.6655	0.6943	0.049*
C10	0.67976 (9)	0.61342 (9)	0.79987 (9)	0.02103 (16)
C11	0.66155 (10)	0.56408 (10)	0.93308 (9)	0.02507 (17)
C12	0.57765 (11)	0.65810 (12)	0.97643 (10)	0.0316 (2)
H12	0.5617	0.6257	1.0662	0.038*
C13	0.51689 (11)	0.79804 (12)	0.89118 (11)	0.0324 (2)
C14	0.54134 (11)	0.84480 (10)	0.75999 (11)	0.0306 (2)
H14	0.5027	0.9412	0.7019	0.037*
C15	0.62119 (10)	0.75379 (10)	0.71134 (9)	0.02509 (17)
C16	0.73039 (13)	0.41372 (12)	1.02726 (11)	0.0361 (2)
H16A	0.8280	0.4010	1.0384	0.054*
H16B	0.7184	0.3503	0.9933	0.054*
H16C	0.6896	0.3920	1.1114	0.054*
C17	0.42260 (16)	0.89708 (17)	0.93916 (17)	0.0527 (4)
H17A	0.4363	0.8567	1.0339	0.079*
H17B	0.3277	0.9109	0.9158	0.079*
H17C	0.4426	0.9880	0.8989	0.079*
C18	0.63861 (13)	0.80407 (12)	0.56796 (10)	0.0363 (2)
H18A	0.6251	0.9060	0.5266	0.054*
H18B	0.5713	0.7828	0.5297	0.054*
H18C	0.7308	0.7562	0.5541	0.054*
C19	0.79893 (10)	0.10010 (11)	0.54297 (10)	0.02763 (19)
H19A	0.7231	0.0670	0.5926	0.033*
H19B	0.8700	0.0172	0.5434	0.033*
C20	0.74631 (12)	0.20307 (13)	0.40350 (11)	0.0331 (2)
H20A	0.8205	0.2380	0.3545	0.050*
H20B	0.6717	0.2824	0.4029	0.050*
H20C	0.7129	0.1552	0.3633	0.050*
C21	0.97891 (9)	0.06971 (10)	0.69446 (10)	0.02640 (18)
H21A	1.0052	0.1202	0.7372	0.032*
H21B	1.0547	0.0489	0.6413	0.032*
C22	0.96184 (11)	−0.06949 (10)	0.79938 (11)	0.0313 (2)
H22A	0.9405	−0.1225	0.7567	0.038*
H22B	1.0496	−0.1263	0.8512	0.038*
C23	0.85034 (12)	−0.05228 (12)	0.89113 (11)	0.0352 (2)
H23A	0.8677	0.0063	0.9295	0.042*
H23B	0.7610	−0.0024	0.8409	0.042*
C24	0.84413 (15)	−0.19306 (14)	0.99966 (13)	0.0455 (3)
H24A	0.9303	−0.2401	1.0531	0.068*
H24B	0.8293	−0.2523	0.9621	0.068*
H24C	0.7688	−0.1775	1.0538	0.068*

	U11	U22	U33	U12	U13	U23
N1	0.0157 (3)	0.0244 (3)	0.0239 (3)	−0.0046 (2)	0.0023 (2)	−0.0136 (3)
N2	0.0178 (3)	0.0246 (3)	0.0247 (3)	−0.0066 (3)	0.0031 (2)	−0.0142 (3)
N3	0.0175 (3)	0.0220 (3)	0.0271 (4)	−0.0050 (2)	0.0014 (2)	−0.0146 (3)
N4	0.0213 (3)	0.0227 (3)	0.0268 (4)	−0.0027 (3)	0.0018 (3)	−0.0155 (3)
C1	0.0163 (3)	0.0249 (4)	0.0216 (4)	−0.0061 (3)	0.0024 (3)	−0.0119 (3)
C2	0.0179 (3)	0.0192 (3)	0.0189 (3)	−0.0038 (3)	0.0021 (3)	−0.0096 (3)
C3	0.0152 (3)	0.0190 (3)	0.0194 (3)	−0.0035 (2)	0.0015 (2)	−0.0093 (3)
C4	0.0151 (3)	0.0226 (4)	0.0234 (4)	−0.0045 (3)	0.0017 (3)	−0.0105 (3)
C5	0.0181 (3)	0.0237 (4)	0.0265 (4)	−0.0065 (3)	0.0008 (3)	−0.0120 (3)
C6	0.0164 (3)	0.0189 (3)	0.0198 (3)	−0.0040 (3)	0.0013 (3)	−0.0099 (3)
C7	0.0166 (4)	0.0387 (5)	0.0354 (5)	−0.0096 (3)	0.0040 (3)	−0.0219 (4)
C8	0.0163 (3)	0.0323 (5)	0.0346 (5)	−0.0069 (3)	0.0055 (3)	−0.0165 (4)
C9	0.0258 (4)	0.0348 (5)	0.0481 (6)	−0.0129 (4)	0.0015 (4)	−0.0242 (5)
C10	0.0205 (4)	0.0219 (4)	0.0240 (4)	−0.0047 (3)	0.0012 (3)	−0.0139 (3)
C11	0.0267 (4)	0.0279 (4)	0.0233 (4)	−0.0090 (3)	0.0006 (3)	−0.0128 (3)
C12	0.0343 (5)	0.0409 (5)	0.0287 (5)	−0.0131 (4)	0.0069 (4)	−0.0227 (4)
C13	0.0308 (5)	0.0364 (5)	0.0419 (6)	−0.0084 (4)	0.0066 (4)	−0.0290 (5)
C14	0.0317 (5)	0.0232 (4)	0.0380 (5)	−0.0020 (3)	0.0000 (4)	−0.0180 (4)
C15	0.0274 (4)	0.0222 (4)	0.0259 (4)	−0.0045 (3)	0.0011 (3)	−0.0124 (3)
C16	0.0404 (6)	0.0331 (5)	0.0269 (5)	−0.0091 (4)	−0.0038 (4)	−0.0064 (4)
C17	0.0517 (8)	0.0556 (8)	0.0706 (10)	−0.0091 (6)	0.0167 (7)	−0.0508 (8)
C18	0.0464 (6)	0.0290 (5)	0.0254 (5)	−0.0040 (4)	0.0022 (4)	−0.0094 (4)
C19	0.0304 (4)	0.0284 (4)	0.0321 (5)	−0.0080 (3)	0.0051 (4)	−0.0210 (4)
C20	0.0340 (5)	0.0419 (6)	0.0310 (5)	−0.0103 (4)	0.0019 (4)	−0.0230 (4)
C21	0.0199 (4)	0.0251 (4)	0.0323 (5)	0.0000 (3)	0.0026 (3)	−0.0152 (4)
C22	0.0313 (5)	0.0232 (4)	0.0346 (5)	0.0010 (3)	0.0004 (4)	−0.0138 (4)
C23	0.0371 (5)	0.0291 (5)	0.0316 (5)	−0.0034 (4)	0.0041 (4)	−0.0107 (4)
C24	0.0464 (7)	0.0379 (6)	0.0376 (6)	−0.0104 (5)	0.0024 (5)	−0.0050 (5)

N1—C1	1.3332 (11)	C13—C14	1.3904 (16)
N1—C6	1.3422 (11)	C13—C17	1.5100 (15)
N2—C2	1.3425 (11)	C14—C15	1.3959 (13)
N2—C1	1.3505 (11)	C14—H14	0.9500
N3—C6	1.3676 (11)	C15—C18	1.5035 (15)
N3—C5	1.3972 (11)	C16—H16A	0.9800
N3—C10	1.4331 (11)	C16—H16B	0.9800
N4—C2	1.3860 (10)	C16—H16C	0.9800
N4—C19	1.4692 (12)	C17—H17A	0.9800
N4—C21	1.4700 (12)	C17—H17B	0.9800
C1—C7	1.5023 (12)	C17—H17C	0.9800
C2—C3	1.4190 (11)	C18—H18A	0.9800
C3—C6	1.4095 (11)	C18—H18B	0.9800
C3—C4	1.4458 (11)	C18—H18C	0.9800
C4—C5	1.3743 (12)	C19—C20	1.5207 (16)
C4—C8	1.5020 (12)	C19—H19A	0.9900
C5—C9	1.4923 (13)	C19—H19B	0.9900
C7—H7A	0.9800	C20—H20A	0.9800
C7—H7B	0.9800	C20—H20B	0.9800
C7—H7C	0.9800	C20—H20C	0.9800
C8—H8A	0.9800	C21—C22	1.5280 (15)
C8—H8B	0.9800	C21—H21A	0.9900
C8—H8C	0.9800	C21—H21B	0.9900
C9—H9A	0.9800	C22—C23	1.5261 (16)
C9—H9B	0.9800	C22—H22A	0.9900
C9—H9C	0.9800	C22—H22B	0.9900
C10—C15	1.3980 (13)	C23—C24	1.5194 (17)
C10—C11	1.3981 (13)	C23—H23A	0.9900
C11—C12	1.3949 (14)	C23—H23B	0.9900
C11—C16	1.5068 (15)	C24—H24A	0.9800
C12—C13	1.3890 (17)	C24—H24B	0.9800
C12—H12	0.9500	C24—H24C	0.9800
C1—N1—C6	112.50 (7)	C15—C14—H14	119.1
C2—N2—C1	119.06 (7)	C14—C15—C10	117.71 (9)
C6—N3—C5	108.48 (7)	C14—C15—C18	120.94 (9)
C6—N3—C10	124.21 (7)	C10—C15—C18	121.30 (8)
C5—N3—C10	127.29 (7)	C11—C16—H16A	109.5
C2—N4—C19	117.58 (7)	C11—C16—H16B	109.5
C2—N4—C21	118.08 (7)	H16A—C16—H16B	109.5
C19—N4—C21	115.32 (7)	C11—C16—H16C	109.5
N1—C1—N2	127.02 (8)	H16A—C16—H16C	109.5
N1—C1—C7	117.04 (8)	H16B—C16—H16C	109.5
N2—C1—C7	115.94 (8)	C13—C17—H17A	109.5
N2—C2—N4	117.28 (7)	C13—C17—H17B	109.5
N2—C2—C3	119.88 (7)	H17A—C17—H17B	109.5
N4—C2—C3	122.82 (7)	C13—C17—H17C	109.5
C6—C3—C2	113.94 (7)	H17A—C17—H17C	109.5
C6—C3—C4	106.79 (7)	H17B—C17—H17C	109.5
C2—C3—C4	139.21 (8)	C15—C18—H18A	109.5
C5—C4—C3	106.48 (7)	C15—C18—H18B	109.5
C5—C4—C8	124.37 (8)	H18A—C18—H18B	109.5
C3—C4—C8	128.84 (8)	C15—C18—H18C	109.5
C4—C5—N3	109.62 (7)	H18A—C18—H18C	109.5
C4—C5—C9	129.98 (8)	H18B—C18—H18C	109.5
N3—C5—C9	120.38 (8)	N4—C19—C20	112.44 (8)
N1—C6—N3	124.15 (7)	N4—C19—H19A	109.1
N1—C6—C3	127.23 (7)	C20—C19—H19A	109.1
N3—C6—C3	108.55 (7)	N4—C19—H19B	109.1
C1—C7—H7A	109.5	C20—C19—H19B	109.1
C1—C7—H7B	109.5	H19A—C19—H19B	107.8
H7A—C7—H7B	109.5	C19—C20—H20A	109.5
C1—C7—H7C	109.5	C19—C20—H20B	109.5
H7A—C7—H7C	109.5	H20A—C20—H20B	109.5
H7B—C7—H7C	109.5	C19—C20—H20C	109.5
C4—C8—H8A	109.5	H20A—C20—H20C	109.5
C4—C8—H8B	109.5	H20B—C20—H20C	109.5
H8A—C8—H8B	109.5	N4—C21—C22	114.50 (8)
C4—C8—H8C	109.5	N4—C21—H21A	108.6
H8A—C8—H8C	109.5	C22—C21—H21A	108.6
H8B—C8—H8C	109.5	N4—C21—H21B	108.6
C5—C9—H9A	109.5	C22—C21—H21B	108.6
C5—C9—H9B	109.5	H21A—C21—H21B	107.6
H9A—C9—H9B	109.5	C23—C22—C21	113.98 (8)
C5—C9—H9C	109.5	C23—C22—H22A	108.8
H9A—C9—H9C	109.5	C21—C22—H22A	108.8
H9B—C9—H9C	109.5	C23—C22—H22B	108.8
C15—C10—C11	122.03 (8)	C21—C22—H22B	108.8
C15—C10—N3	119.07 (8)	H22A—C22—H22B	107.7
C11—C10—N3	118.86 (8)	C24—C23—C22	112.13 (10)
C12—C11—C10	118.08 (9)	C24—C23—H23A	109.2
C12—C11—C16	120.88 (9)	C22—C23—H23A	109.2
C10—C11—C16	121.05 (9)	C24—C23—H23B	109.2
C13—C12—C11	121.45 (10)	C22—C23—H23B	109.2
C13—C12—H12	119.3	H23A—C23—H23B	107.9
C11—C12—H12	119.3	C23—C24—H24A	109.5
C12—C13—C14	118.91 (9)	C23—C24—H24B	109.5
C12—C13—C17	120.70 (11)	H24A—C24—H24B	109.5
C14—C13—C17	120.36 (11)	C23—C24—H24C	109.5
C13—C14—C15	121.74 (9)	H24A—C24—H24C	109.5
C13—C14—H14	119.1	H24B—C24—H24C	109.5
C6—N1—C1—N2	4.24 (13)	C10—N3—C6—C3	−179.03 (8)
C6—N1—C1—C7	−177.02 (8)	C2—C3—C6—N1	−3.57 (13)
C2—N2—C1—N1	−1.29 (14)	C4—C3—C6—N1	174.07 (8)
C2—N2—C1—C7	179.97 (8)	C2—C3—C6—N3	179.42 (7)
C1—N2—C2—N4	176.89 (8)	C4—C3—C6—N3	−2.94 (9)
C1—N2—C2—C3	−4.58 (12)	C6—N3—C10—C15	−90.87 (11)
C19—N4—C2—N2	11.95 (12)	C5—N3—C10—C15	87.33 (11)
C21—N4—C2—N2	−133.70 (9)	C6—N3—C10—C11	87.18 (11)
C19—N4—C2—C3	−166.54 (8)	C5—N3—C10—C11	−94.62 (11)
C21—N4—C2—C3	47.81 (12)	C15—C10—C11—C12	2.55 (14)
N2—C2—C3—C6	6.56 (12)	N3—C10—C11—C12	−175.43 (8)
N4—C2—C3—C6	−174.99 (8)	C15—C10—C11—C16	−177.49 (9)
N2—C2—C3—C4	−169.98 (10)	N3—C10—C11—C16	4.53 (13)
N4—C2—C3—C4	8.47 (16)	C10—C11—C12—C13	−2.01 (15)
C6—C3—C4—C5	2.29 (9)	C16—C11—C12—C13	178.03 (10)
C2—C3—C4—C5	178.98 (10)	C11—C12—C13—C14	−0.34 (16)
C6—C3—C4—C8	−171.43 (9)	C11—C12—C13—C17	177.93 (11)
C2—C3—C4—C8	5.26 (17)	C12—C13—C14—C15	2.29 (16)
C3—C4—C5—N3	−0.82 (10)	C17—C13—C14—C15	−175.98 (11)
C8—C4—C5—N3	173.25 (8)	C13—C14—C15—C10	−1.77 (15)
C3—C4—C5—C9	−179.00 (10)	C13—C14—C15—C18	175.79 (11)
C8—C4—C5—C9	−4.92 (16)	C11—C10—C15—C14	−0.71 (14)
C6—N3—C5—C4	−1.01 (10)	N3—C10—C15—C14	177.27 (8)
C10—N3—C5—C4	−179.44 (8)	C11—C10—C15—C18	−178.26 (10)
C6—N3—C5—C9	177.37 (9)	N3—C10—C15—C18	−0.28 (14)
C10—N3—C5—C9	−1.06 (14)	C2—N4—C19—C20	71.72 (11)
C1—N1—C6—N3	175.04 (8)	C21—N4—C19—C20	−141.70 (9)
C1—N1—C6—C3	−1.54 (13)	C2—N4—C21—C22	91.90 (10)
C5—N3—C6—N1	−174.64 (8)	C19—N4—C21—C22	−54.51 (11)
C10—N3—C6—N1	3.84 (14)	N4—C21—C22—C23	−60.09 (12)
C5—N3—C6—C3	2.48 (10)	C21—C22—C23—C24	−175.74 (10)