Antalarmin

Slauson, S.R.; Rimoldi, J.M.; Fronczek, F.R.

doi:10.1107/S1600536808023775

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages o1650-o1651

doi:10.1107/S1600536808023775

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Antalarmin

Stephen R. Slauson,^a John M. Rimoldi ^a and Frank R. Fronczek ^b ^*

^aUniversity of Mississippi, Department of Medicinal Chemistry, University, MS 38677, USA, and ^bDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
^*Correspondence e-mail: ffroncz@lsu.edu

(Received 9 July 2008; accepted 27 July 2008; online 31 July 2008)

In the molecule of the title compund [systematic name: N-butyl-N-ethyl-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine], C₂₄H₃₄N₄, the pyrrolopyrimidine 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_r = 378.55
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.142
S = 1.03
8550 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

Comment top

Corticotropin releasing factor (CRF) is a 41 amino acid hormone that has been implicated in the stress response cascade (Vale et al.,1981). This action is achieved by the release of adrenocorticotropic hormone (ACTH) by stimulation of the hypothalamic-pituitary-adrenal (HPA) axis (Rivier & Vale, 1983). CRF creates this release by binding to G-protein coupled receptors designated as CRF1 and CRF2 (Steckler & Holsboer, 1999). The CRF1 receptor has been designated as the subtype responsible for the physiological reaction to stress (Dieterich et al., 1997). Both subtypes are found widely distributed in the central nervous system and have been correlated to numerous other responses (Hsin et al., 2002).

In the search for non-peptide, selective antagonists for CRF1, antalarmin (1) has emerged as a lead candidate. Analogs have been developed to increase activity and decrease LogP, yet none have been reported as superior in overall performance (Gross et al., 2005; Hsin et al., 2002; Chorvat et al., 1999). Antalarmin has shown anxiolytic activity in primates, as well as a reduction of self-administration of ethanol in addiction models (Habib et al., 2000; Chu et al., 2007). Recently, detailed toxicology has been reported indicating a favorable safety profile and suggesting that clinical trials may begin soon (Horn et al., 2008).

Data collection was initially attempted at 90 K, but an apparent phase change destroyed the crystal at that temperature. Thus, data were collected at 150 K, and the structure based upon those data is presented in Fig. 1. The pyrimidine and pyrrole rings are slightly nonplanar, exhibiting maximum deviations 0.036 (1) Å (for C2) and 0.016 (1) Å (for C6), respectively. These planes form a dihedral angle of 5.3 (2)°. The phenyl group is nearly orthogonal to the pyrrolopyrimidine ring system, forming dihedral angles of 88.52 (2)° with the pyrimidine and 86.40 (3)° with the pyrrole plane. N3 is trigonal planar, lying 0.011 (1) Å from the plane defined by the three C atoms bonded to it. Amine nitrogen N4 is flattened pyramidal, lying 0.252 (1) Å from the plane of C2, C19 and C21, with C–N–C angles in the range 115.32 (7)–118.08 (7)°. The n-butyl group is extended except for its attachment to N, with C19—N4—C21—C22 torsion angle -54.51 (11)°.

No other pyrrolopyrimidines having substituents at N4 are found in the Cambridge Structural Database (version 5.29, Nov. 2007; Allen, 2002). The structure of a similar molecule, ICAKOM, having a cyclopentyl group at N3 and a 4-phenoxyphenyl group at C4, has been reported Banić Tomišić et al. (2001).

Related literature top

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 top

Synthesis of antalarmin has been reported (Greiner et al., 2002). It was crystallized from acetonitrile:water to afford translucent crystals: Mp = 85.9–86.1°C; HRMS m/z expected: 379.2862 found: 379.2878; CHN analysis for C₂₄H₃₄N₄ expected: C 76.15, H 9.05, N 14.80%; found: C 76.07, H 8.69, N 14.90%.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Ellipsoids at the 50% level, with H atoms having arbitrary radius.

N-butyl-N-ethyl-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)- 7H-pyrrolo[2,3-d]pyrimidin-4-amine top

Crystal data top

C₂₄H₃₄N₄	Z = 2
M_r = 378.55	F(000) = 412
Triclinic, P1	D_x = 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 = 2.5–34.3°
c = 11.5029 (12) Å	µ = 0.07 mm⁻¹
α = 63.646 (6)°	T = 150 K
β = 85.669 (6)°	Fragment, colorless
γ = 73.036 (5)°	0.40 × 0.37 × 0.30 mm
V = 1117.69 (19) Å³

Data collection top

Nonius KappaCCD diffractometer with Oxford Cryostream	6916 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 34.3°, θ_min = 2.6°
ω and ϕ scans	h = −15→16
35420 measured reflections	k = −17→16
8550 independent reflections	l = −17→17

Refinement top

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.142	w = 1/[σ²(F_o²) + (0.0675P)² + 0.2841P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
8550 reflections	Δρ_max = 0.44 e Å⁻³
262 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	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)

Crystal data top

C₂₄H₃₄N₄	γ = 73.036 (5)°
M_r = 378.55	V = 1117.69 (19) Å³
Triclinic, P1	Z = 2
a = 10.2656 (10) Å	Mo Kα radiation
b = 11.0655 (11) Å	µ = 0.07 mm⁻¹
c = 11.5029 (12) Å	T = 150 K
α = 63.646 (6)°	0.40 × 0.37 × 0.30 mm
β = 85.669 (6)°

Data collection top

Nonius KappaCCD diffractometer with Oxford Cryostream	6916 reflections with I > 2σ(I)
35420 measured reflections	R_int = 0.023
8550 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.03	Δρ_max = 0.44 e Å⁻³
8550 reflections	Δρ_min = −0.24 e Å⁻³
262 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₄H₃₄N₄
M_r	378.55
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	10.2656 (10), 11.0655 (11), 11.5029 (12)
α, β, γ (°)	63.646 (6), 85.669 (6), 73.036 (5)
V (Å³)	1117.69 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.37 × 0.30

Data collection
Diffractometer	Nonius KappaCCD diffractometer with Oxford Cryostream
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	35420, 8550, 6916
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.793

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.142, 1.03
No. of reflections	8550
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.24

Computer programs: COLLECT (Nonius, 2000), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

The purchase of the diffractometer was made possible by grant No. LEQSF (1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

References

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