9-Methyl-2,6-di-p-tolyl-2,3,6,7-tetra­hydro-1H,5H-pyrimido[5,6,1-ij]quinazoline

Mahon, A.B.; Craig, D.C.; Try, A.C.

doi:10.1107/S1600536807049173

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9-Methyl-2,6-di-p-tolyl-2,3,6,7-tetrahydro-1H,5H-pyrimido[5,6,1-ij]quinazoline

A. B. Mahon, D. C. Craig and A. C. Try

The title compound, C₂₅H₂₇N₃, possesses an essentially planar, fused tricyclic platform, from which two p-tolyl rings project on the same face to create a hydrophobic pocket.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049173/hg2304sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049173/hg2304Isup2.hkl Contains datablock I

CCDC reference: 667352

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.006 Å
R factor = 0.058
wR factor = 0.065
Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5946
            Proportion of unique data used    0.5863
            Ratio reflections to parameters   8.3740
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       8.37
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         27

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Compound (I) was first reported as one of several products formed in the reaction of p-toluidine with aqueous formaldehyde solution in hydrochloric acid, in approximately 3% yield (Farrar, 1964). An analogous compound, with methoxy groups in place of the methyl groups, was proposed when p-anisidine was used instead of p-toluidine. Compound (I) was also obtained 26% yield from a 1:1 reaction of hexamethylene tetraamine and p-toluidine in trifluoroacetic acid (Johnson et al., 1993). These compounds are related to 3-phenyl-3,4-dihydroquinazolines that have been isolated as impurities in the synthesis of numerous Tröger's base analogues (von Walther & Bamberg, 1906; Eisner & Wagner, 1934; Maffei, 1928; Maffei, 1929; Wagner & Eisner, 1937; Smith, 1948; Becker et al., 1993; Bhuiyan et al., 2007).

The x-ray crystal structure reported here (Fig. 1) confirms the earlier stuctural assignments that have been proposed for compound (I). The tetrasubstituted aromatic ring forms the base of a cavity, with the 'walls' provided by the two p-di-substituted benzene rings.

Related literature top

For related literature, see: Becker et al. (1993); Bhuiyan et al. (2007); Eisner & Wagner (1934); Farrar (1964); Johnson et al. (1993); Maffei (1928, 1929); Smith & Schubert (1948); Walther & Bamberg (1906).

For related literature, see: Ibers & Hamilton (1974); Wagner & Eisner (1937).

Experimental top

The title compound (I) was isolated as a minor impurity in the synthesis of Tröger's base, using p-toluidine and paraformaldehyde in trifluoroacetic acid (TFA). p-Toluidine (30 g, 280 mmol) and p-formaldehyde (13.5 g,489 mmol) were dissolved in trifluoroacetic acid (300 ml) and stirred in the dark under an atmosphere of argon for 3 days before pouring the red reaction mixture over ice (200 g) and basifying the mixture with 26% ammonia solution (300 ml). The resultant yellow mixture was extracted with dichloromethane (3 x 80 ml) and the organic layers were combined before washing with saturated sodium carbonate solution (2 x 100 ml), brine (100 ml) and then drying over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the crude material was purified by column chromatography (silica gel, dichloromethane) to afford (I) as a white solid (1.55 g, 5%). Crystals of (I) were produced by slow evaporation of a methanol solution.

Structure description top

For related literature, see: Ibers & Hamilton (1974); Wagner & Eisner (1937).

Computing details top

Data collection: CAD-4 (Schagen et al., 1989); cell refinement: CAD-4 (Schagen et al., 1989); data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: RAELS (Rae, 1996); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: local programs.

Figures top

	Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound, with ellipsoids at the 10% probability level. H atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The preparation of (I).

9-Methyl-2,6-di-p-tolyl-2,3,6,7-tetrahydro-1H,5H- pyrimido[5,6,1-ij]quinazoline top

Crystal data top

C₂₅H₂₇N₃	D_x = 1.19 Mg m⁻³
M_r = 369.5	Melting point: 421 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.035 (3) Å	Cell parameters from 11 reflections
b = 20.805 (7) Å	θ = 10–11°
c = 11.790 (3) Å	µ = 0.07 mm⁻¹
β = 110.95 (1)°	T = 294 K
V = 2070 (1) Å³	Prism, colourless
Z = 4	0.30 × 0.08 × 0.05 mm
F(000) = 792.0

Data collection top

Enraf–Nonius CAD-4 diffractometer	θ_max = 25°
ω–2θ scans	h = −10→10
3813 measured reflections	k = 0→24
3628 independent reflections	l = 0→14
2127 reflections with I > 2σ(I)	1 standard reflections every 30 min
R_int = 0.023	intensity decay: none

Refinement top

Refinement on F	0 restraints
R[F² > 2σ(F²)] = 0.058	H-atom parameters not refined
wR(F²) = 0.065	w = 1/[σ²(F) + 0.0004F²]
S = 1.85	(Δ/σ)_max = 0.002
2127 reflections	Δρ_max = 0.33 e Å⁻³
254 parameters	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₅H₂₇N₃	V = 2070 (1) Å³
M_r = 369.5	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.035 (3) Å	µ = 0.07 mm⁻¹
b = 20.805 (7) Å	T = 294 K
c = 11.790 (3) Å	0.30 × 0.08 × 0.05 mm
β = 110.95 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.023
3813 measured reflections	1 standard reflections every 30 min
3628 independent reflections	intensity decay: none
2127 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.065	H-atom parameters not refined
S = 1.85	Δρ_max = 0.33 e Å⁻³
2127 reflections	Δρ_min = −0.34 e Å⁻³
254 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.1834 (3)	0.2545 (1)	0.5530 (2)	0.0630 (8)
N2	−0.0410 (3)	0.2116 (2)	0.3932 (2)	0.0674 (8)
N3	0.4565 (3)	0.2671 (1)	0.6746 (2)	0.0629 (8)
C1	0.0391 (4)	0.2186 (2)	0.5239 (3)	0.072 (1)
C2	−0.0829 (4)	0.2753 (2)	0.3394 (3)	0.075 (1)
C3	0.0602 (4)	0.3184 (2)	0.3720 (3)	0.0606 (9)
C4	0.0696 (5)	0.3696 (2)	0.2992 (3)	0.072 (1)
C5	0.2015 (6)	0.4082 (2)	0.3281 (3)	0.078 (1)
C6	0.3297 (5)	0.3954 (2)	0.4353 (4)	0.075 (1)
C7	0.3221 (4)	0.3454 (2)	0.5114 (3)	0.0623 (9)
C8	0.4565 (4)	0.3331 (2)	0.6317 (3)	0.072 (1)
C9	0.2996 (4)	0.2530 (2)	0.6763 (3)	0.070 (1)
C10	0.1887 (4)	0.3065 (2)	0.4799 (3)	0.0572 (8)
C11	0.2124 (6)	0.4629 (2)	0.2461 (4)	0.118 (2)
C12	0.0224 (4)	0.1667 (2)	0.3334 (3)	0.0596 (9)
C13	−0.0610 (4)	0.1534 (2)	0.2092 (3)	0.074 (1)
C14	−0.0068 (5)	0.1074 (2)	0.1496 (3)	0.076 (1)
C15	0.1288 (5)	0.0722 (2)	0.2063 (3)	0.070 (1)
C16	0.2110 (4)	0.0861 (2)	0.3282 (3)	0.071 (1)
C17	0.1597 (4)	0.1323 (2)	0.3897 (3)	0.0645 (9)
C18	0.1839 (5)	0.0208 (2)	0.1407 (3)	0.092 (1)
C19	0.5173 (3)	0.2185 (2)	0.6180 (3)	0.0554 (8)
C20	0.5351 (4)	0.1567 (2)	0.6634 (3)	0.0643 (9)
C21	0.5978 (4)	0.1086 (2)	0.6143 (3)	0.071 (1)
C22	0.6484 (4)	0.1206 (2)	0.5163 (3)	0.0671 (9)
C23	0.6312 (4)	0.1823 (2)	0.4732 (3)	0.0620 (9)
C24	0.5658 (4)	0.2311 (2)	0.5200 (3)	0.0573 (9)
C25	0.7166 (5)	0.0679 (2)	0.4629 (4)	0.099 (1)
H1C1	−0.0330	0.2414	0.5580	0.072
H2C1	0.0644	0.1749	0.5613	0.072
H1C2	−0.1625	0.2951	0.3698	0.075
H2C2	−0.1300	0.2709	0.2490	0.075
HC4	−0.0227	0.3787	0.2233	0.072
HC6	0.4274	0.4225	0.4573	0.075
H1C8	0.4449	0.3632	0.6941	0.072
H2C8	0.5596	0.3414	0.6208	0.072
H1C9	0.2709	0.2859	0.7268	0.070
H2C9	0.2999	0.2094	0.7119	0.070
H1C11	0.2273	0.5044	0.2916	0.118
H2C11	0.3044	0.4555	0.2196	0.118
H3C11	0.1125	0.4648	0.1732	0.118
HC13	−0.1603	0.1777	0.1642	0.074
HC14	−0.0683	0.0992	0.0618	0.076
HC16	0.3104	0.0618	0.3727	0.071
HC17	0.2234	0.1410	0.4771	0.064
H1C18	0.1362	−0.0214	0.1499	0.092
H2C18	0.1500	0.0319	0.0526	0.092
H3C18	0.3021	0.0176	0.1760	0.092
HC20	0.5017	0.1466	0.7337	0.064
HC21	0.6077	0.0642	0.6488	0.071
HC23	0.6676	0.1927	0.4046	0.062
HC24	0.5533	0.2752	0.4839	0.057
H1C25	0.7710	0.0358	0.5275	0.099
H2C25	0.6295	0.0463	0.3960	0.099
H3C25	0.7948	0.0866	0.4298	0.099

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.060 (2)	0.093 (2)	0.037 (2)	−0.004 (2)	0.018 (1)	0.007 (1)
N2	0.060 (2)	0.103 (2)	0.044 (2)	−0.001 (2)	0.023 (1)	0.005 (2)
N3	0.065 (2)	0.080 (2)	0.044 (2)	0.002 (2)	0.019 (1)	−0.010 (1)
C1	0.066 (2)	0.114 (3)	0.045 (2)	−0.011 (2)	0.032 (2)	−0.002 (2)
C2	0.063 (2)	0.111 (3)	0.053 (2)	0.014 (2)	0.024 (2)	0.002 (2)
C3	0.062 (2)	0.084 (3)	0.042 (2)	0.012 (2)	0.027 (2)	−0.001 (2)
C4	0.093 (3)	0.088 (3)	0.046 (2)	0.025 (2)	0.040 (2)	0.009 (2)
C5	0.110 (3)	0.076 (3)	0.069 (3)	0.021 (3)	0.059 (3)	0.011 (2)
C6	0.088 (3)	0.074 (3)	0.080 (3)	0.005 (2)	0.049 (2)	−0.001 (2)
C7	0.070 (2)	0.070 (2)	0.055 (2)	0.005 (2)	0.031 (2)	−0.004 (2)
C8	0.072 (3)	0.076 (3)	0.067 (2)	−0.001 (2)	0.022 (2)	−0.018 (2)
C9	0.067 (2)	0.110 (3)	0.036 (2)	0.007 (2)	0.022 (2)	−0.002 (2)
C10	0.062 (2)	0.075 (2)	0.044 (2)	0.008 (2)	0.030 (2)	0.002 (2)
C11	0.177 (5)	0.099 (3)	0.102 (3)	0.023 (3)	0.081 (3)	0.031 (3)
C12	0.052 (2)	0.086 (3)	0.045 (2)	−0.010 (2)	0.022 (2)	0.006 (2)
C13	0.062 (2)	0.106 (3)	0.046 (2)	−0.010 (2)	0.009 (2)	0.006 (2)
C14	0.086 (3)	0.097 (3)	0.042 (2)	−0.015 (2)	0.020 (2)	−0.003 (2)
C15	0.085 (3)	0.078 (3)	0.050 (2)	−0.014 (2)	0.028 (2)	0.002 (2)
C16	0.076 (3)	0.080 (3)	0.054 (2)	−0.009 (2)	0.020 (2)	0.001 (2)
C17	0.066 (2)	0.086 (3)	0.039 (2)	−0.005 (2)	0.015 (2)	0.005 (2)
C18	0.133 (4)	0.082 (3)	0.068 (2)	−0.008 (3)	0.045 (3)	−0.004 (2)
C19	0.049 (2)	0.077 (2)	0.037 (2)	0.001 (2)	0.011 (2)	−0.002 (2)
C20	0.071 (2)	0.079 (2)	0.045 (2)	0.002 (2)	0.023 (2)	0.006 (2)
C21	0.083 (3)	0.072 (3)	0.058 (2)	0.006 (2)	0.024 (2)	0.010 (2)
C22	0.067 (2)	0.077 (3)	0.057 (2)	0.003 (2)	0.022 (2)	−0.007 (2)
C23	0.060 (2)	0.081 (3)	0.047 (2)	−0.001 (2)	0.022 (2)	−0.003 (2)
C24	0.057 (2)	0.072 (2)	0.044 (2)	0.002 (2)	0.020 (2)	0.005 (2)
C25	0.119 (4)	0.096 (3)	0.094 (3)	0.017 (3)	0.051 (3)	−0.014 (2)

Geometric parameters (Å, º) top

N1—C1	1.434 (4)	C11—H3C11	1.000
N1—C9	1.458 (4)	C12—C13	1.414 (4)
N1—C10	1.393 (4)	C12—C17	1.380 (4)
N2—C1	1.457 (4)	C13—C14	1.377 (5)
N2—C2	1.460 (4)	C13—HC13	1.000
N2—C12	1.409 (4)	C14—C15	1.378 (5)
N3—C8	1.463 (4)	C14—HC14	1.000
N3—C9	1.455 (4)	C15—C16	1.392 (4)
N3—C19	1.425 (4)	C15—C18	1.505 (5)
C1—H1C1	1.000	C16—C17	1.380 (4)
C1—H2C1	1.000	C16—HC16	1.000
C2—C3	1.506 (5)	C17—HC17	1.000
C2—H1C2	1.000	C18—H1C18	1.000
C2—H2C2	1.000	C18—H2C18	1.000
C3—C4	1.389 (4)	C18—H3C18	1.000
C3—C10	1.404 (4)	C19—C20	1.381 (4)
C4—C5	1.375 (5)	C19—C24	1.399 (4)
C4—HC4	1.000	C20—C21	1.376 (4)
C5—C6	1.401 (5)	C20—HC20	1.000
C5—C11	1.519 (5)	C21—C22	1.408 (4)
C6—C7	1.392 (4)	C21—HC21	1.000
C6—HC6	1.000	C22—C23	1.369 (4)
C7—C8	1.523 (5)	C22—C25	1.502 (5)
C7—C10	1.388 (4)	C23—C24	1.384 (4)
C8—H1C8	1.000	C23—HC23	1.000
C8—H2C8	1.000	C24—HC24	1.000
C9—H1C9	1.000	C25—H1C25	1.000
C9—H2C9	1.000	C25—H2C25	1.000
C11—H1C11	1.000	C25—H3C25	1.000
C11—H2C11	1.000

C1—N1—C9	119.7 (3)	C5—C11—H3C11	109.5
C1—N1—C10	119.1 (3)	H1C11—C11—H2C11	109.5
C9—N1—C10	117.5 (3)	H1C11—C11—H3C11	109.5
C1—N2—C2	108.8 (3)	H2C11—C11—H3C11	109.5
C1—N2—C12	117.3 (3)	N2—C12—C13	119.1 (3)
C2—N2—C12	118.2 (2)	N2—C12—C17	124.1 (3)
C8—N3—C9	108.3 (3)	C13—C12—C17	116.8 (3)
C8—N3—C19	117.1 (3)	C12—C13—C14	120.6 (3)
C9—N3—C19	113.8 (3)	C12—C13—HC13	119.7
N1—C1—N2	111.8 (2)	C14—C13—HC13	119.7
N1—C1—H1C1	108.9	C13—C14—C15	122.6 (3)
N1—C1—H2C1	108.9	C13—C14—HC14	118.7
N2—C1—H1C1	108.9	C15—C14—HC14	118.7
N2—C1—H2C1	108.9	C14—C15—C16	116.4 (3)
H1C1—C1—H2C1	109.5	C14—C15—C18	121.9 (3)
N2—C2—C3	111.4 (3)	C16—C15—C18	121.7 (4)
N2—C2—H1C2	109.0	C15—C16—C17	122.1 (3)
N2—C2—H2C2	109.0	C15—C16—HC16	118.9
C3—C2—H1C2	109.0	C17—C16—HC16	118.9
C3—C2—H2C2	109.0	C12—C17—C16	121.5 (3)
H1C2—C2—H2C2	109.5	C12—C17—HC17	119.3
C2—C3—C4	122.4 (3)	C16—C17—HC17	119.3
C2—C3—C10	118.8 (3)	C15—C18—H1C18	109.5
C4—C3—C10	118.8 (3)	C15—C18—H2C18	109.5
C3—C4—C5	122.3 (3)	C15—C18—H3C18	109.5
C3—C4—HC4	118.9	H1C18—C18—H2C18	109.5
C5—C4—HC4	118.9	H1C18—C18—H3C18	109.5
C4—C5—C6	118.5 (3)	H2C18—C18—H3C18	109.5
C4—C5—C11	121.8 (4)	N3—C19—C20	119.3 (3)
C6—C5—C11	119.7 (4)	N3—C19—C24	122.8 (3)
C5—C6—C7	120.5 (4)	C20—C19—C24	117.8 (3)
C5—C6—HC6	119.7	C19—C20—C21	121.5 (3)
C7—C6—HC6	119.7	C19—C20—HC20	119.2
C6—C7—C8	121.3 (3)	C21—C20—HC20	119.2
C6—C7—C10	120.1 (3)	C20—C21—C22	121.3 (3)
C8—C7—C10	118.6 (3)	C20—C21—HC21	119.4
N3—C8—C7	112.4 (3)	C22—C21—HC21	119.4
N3—C8—H1C8	108.7	C21—C22—C23	116.4 (3)
N3—C8—H2C8	108.7	C21—C22—C25	121.0 (3)
C7—C8—H1C8	108.7	C23—C22—C25	122.6 (3)
C7—C8—H2C8	108.7	C22—C23—C24	123.2 (3)
H1C8—C8—H2C8	109.5	C22—C23—HC23	118.4
N1—C9—N3	109.9 (3)	C24—C23—HC23	118.4
N1—C9—H1C9	109.4	C19—C24—C23	119.8 (3)
N1—C9—H2C9	109.4	C19—C24—HC24	120.1
N3—C9—H1C9	109.4	C23—C24—HC24	120.1
N3—C9—H2C9	109.4	C22—C25—H1C25	109.5
H1C9—C9—H2C9	109.5	C22—C25—H2C25	109.5
N1—C10—C3	119.8 (3)	C22—C25—H3C25	109.5
N1—C10—C7	120.4 (3)	H1C25—C25—H2C25	109.5
C3—C10—C7	119.8 (3)	H1C25—C25—H3C25	109.5
C5—C11—H1C11	109.5	H2C25—C25—H3C25	109.5
C5—C11—H2C11	109.5

C9—N1—C1—N2	−164.5 (3)	C6—C5—C11—H3C11	178.8
C9—N1—C1—H1C1	75.1	C5—C6—C7—C8	−176.6 (3)
C9—N1—C1—H2C1	−44.2	C5—C6—C7—C10	1.9 (5)
C10—N1—C1—N2	37.7 (4)	HC6—C6—C7—C8	3.4
C10—N1—C1—H1C1	−82.7	HC6—C6—C7—C10	−178.1
C10—N1—C1—H2C1	158.0	C6—C7—C8—N3	−158.0 (3)
C1—N1—C9—N3	155.0 (3)	C6—C7—C8—H1C8	81.5
C1—N1—C9—H1C9	−84.9	C6—C7—C8—H2C8	−37.6
C1—N1—C9—H2C9	35.0	C10—C7—C8—N3	23.5 (4)
C10—N1—C9—N3	−46.8 (4)	C10—C7—C8—H1C8	−97.0
C10—N1—C9—H1C9	73.3	C10—C7—C8—H2C8	143.9
C10—N1—C9—H2C9	−166.9	C6—C7—C10—N1	177.1 (3)
C1—N1—C10—C3	−7.2 (4)	C6—C7—C10—C3	−1.2 (4)
C1—N1—C10—C7	174.6 (3)	C8—C7—C10—N1	−4.4 (4)
C9—N1—C10—C3	−165.5 (3)	C8—C7—C10—C3	177.4 (3)
C9—N1—C10—C7	16.3 (4)	N2—C12—C13—C14	−176.5 (3)
C2—N2—C1—N1	−61.7 (3)	N2—C12—C13—HC13	3.5
C2—N2—C1—H1C1	58.7	C17—C12—C13—C14	0.9 (5)
C2—N2—C1—H2C1	178.0	C17—C12—C13—HC13	−179.1
C12—N2—C1—N1	75.8 (4)	N2—C12—C17—C16	175.9 (3)
C12—N2—C1—H1C1	−163.9	N2—C12—C17—HC17	−4.1
C12—N2—C1—H2C1	−44.6	C13—C12—C17—C16	−1.3 (5)
C1—N2—C2—C3	55.2 (3)	C13—C12—C17—HC17	178.7
C1—N2—C2—H1C2	−65.1	C12—C13—C14—C15	0.2 (5)
C1—N2—C2—H2C2	175.4	C12—C13—C14—HC14	−179.8
C12—N2—C2—C3	−81.8 (3)	HC13—C13—C14—C15	−179.8
C12—N2—C2—H1C2	157.9	HC13—C13—C14—HC14	0.2
C12—N2—C2—H2C2	38.4	C13—C14—C15—C16	−0.8 (5)
C1—N2—C12—C13	173.3 (3)	C13—C14—C15—C18	178.3 (3)
C1—N2—C12—C17	−3.9 (4)	HC14—C14—C15—C16	179.2
C2—N2—C12—C13	−53.2 (4)	HC14—C14—C15—C18	−1.7
C2—N2—C12—C17	129.6 (3)	C14—C15—C16—C17	0.3 (5)
C9—N3—C8—C7	−52.9 (3)	C14—C15—C16—HC16	−179.7
C9—N3—C8—H1C8	67.6	C18—C15—C16—C17	−178.7 (3)
C9—N3—C8—H2C8	−173.3	C18—C15—C16—HC16	1.3
C19—N3—C8—C7	77.5 (3)	C14—C15—C18—H1C18	−90.0
C19—N3—C8—H1C8	−162.1	C14—C15—C18—H2C18	30.0
C19—N3—C8—H2C8	−43.0	C14—C15—C18—H3C18	150.0
C8—N3—C9—N1	64.6 (3)	C16—C15—C18—H1C18	89.0
C8—N3—C9—H1C9	−55.5	C16—C15—C18—H2C18	−151.0
C8—N3—C9—H2C9	−175.4	C16—C15—C18—H3C18	−31.0
C19—N3—C9—N1	−67.5 (4)	C15—C16—C17—C12	0.8 (5)
C19—N3—C9—H1C9	172.4	C15—C16—C17—HC17	−179.2
C19—N3—C9—H2C9	52.5	HC16—C16—C17—C12	−179.2
C8—N3—C19—C20	173.4 (3)	HC16—C16—C17—HC17	0.8
C8—N3—C19—C24	−4.2 (4)	N3—C19—C20—C21	−178.0 (3)
C9—N3—C19—C20	−58.9 (4)	N3—C19—C20—HC20	2.0
C9—N3—C19—C24	123.5 (3)	C24—C19—C20—C21	−0.3 (5)
N2—C2—C3—C4	153.9 (3)	C24—C19—C20—HC20	179.7
N2—C2—C3—C10	−26.3 (4)	N3—C19—C24—C23	176.7 (3)
H1C2—C2—C3—C4	−85.8	N3—C19—C24—HC24	−3.3
H1C2—C2—C3—C10	94.0	C20—C19—C24—C23	−0.9 (4)
H2C2—C2—C3—C4	33.6	C20—C19—C24—HC24	179.1
H2C2—C2—C3—C10	−146.5	C19—C20—C21—C22	0.8 (5)
C2—C3—C4—C5	−178.9 (3)	C19—C20—C21—HC21	−179.2
C2—C3—C4—HC4	1.1	HC20—C20—C21—C22	−179.2
C10—C3—C4—C5	1.3 (5)	HC20—C20—C21—HC21	0.8
C10—C3—C4—HC4	−178.7	C20—C21—C22—C23	−0.2 (5)
C2—C3—C10—N1	1.5 (4)	C20—C21—C22—C25	−179.9 (3)
C2—C3—C10—C7	179.8 (3)	HC21—C21—C22—C23	179.8
C4—C3—C10—N1	−178.6 (3)	HC21—C21—C22—C25	0.1
C4—C3—C10—C7	−0.4 (4)	C21—C22—C23—C24	−1.0 (5)
C3—C4—C5—C6	−0.6 (5)	C21—C22—C23—HC23	179.0
C3—C4—C5—C11	178.2 (3)	C25—C22—C23—C24	178.7 (3)
HC4—C4—C5—C6	179.4	C25—C22—C23—HC23	−1.3
HC4—C4—C5—C11	−1.8	C21—C22—C25—H1C25	−30.0
C4—C5—C6—C7	−1.0 (5)	C21—C22—C25—H2C25	90.0
C4—C5—C6—HC6	179.0	C21—C22—C25—H3C25	−150.0
C11—C5—C6—C7	−179.9 (3)	C23—C22—C25—H1C25	150.3
C11—C5—C6—HC6	0.1	C23—C22—C25—H2C25	−89.7
C4—C5—C11—H1C11	120.0	C23—C22—C25—H3C25	30.3
C4—C5—C11—H2C11	−120.0	C22—C23—C24—C19	1.6 (5)
C4—C5—C11—H3C11	0.0	C22—C23—C24—HC24	−178.4
C6—C5—C11—H1C11	−61.2	HC23—C23—C24—C19	−178.4
C6—C5—C11—H2C11	58.8	HC23—C23—C24—HC24	1.6

Experimental details

Crystal data
Chemical formula	C₂₅H₂₇N₃
M_r	369.5
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	9.035 (3), 20.805 (7), 11.790 (3)
β (°)	110.95 (1)
V (Å³)	2070 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.08 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3813, 3628, 2127
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.065, 1.85
No. of reflections	2127
No. of parameters	254
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.34

Computer programs: CAD-4 (Schagen et al., 1989), SIR92 (Altomare et al., 1994), RAELS (Rae, 1996), ORTEPII (Johnson, 1976), local programs.

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