2-(5,6-Di­hydro­benzimidazolo[1,2-c]quinazolin-6-yl)aniline methanol solvate

Booysen, I.; Gerber, T.I.A.; Hosten, E.; Mayer, P.

doi:10.1107/S1600536809021886

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1565

doi:10.1107/S1600536809021886

Open

access

2-(5,6-Dihydrobenzimidazolo[1,2-c]quinazolin-6-yl)aniline methanol solvate

Irvin Booysen,^a Thomas I. A. Gerber,^a ^* Eric Hosten ^a and Peter Mayer ^b

^aDepartment of Chemistry, Nelson Mandela Metropolitan University, 6031 Port Elizabeth, South Africa, and ^bDepartment of Chemistry, Ludiwig-Maximilians University, D-81377 München, Germany
^*Correspondence e-mail: thomas.gerber@nmmu.ac.za

(Received 28 May 2009; accepted 9 June 2009; online 13 June 2009)

In the structure of the title compound, C₂₀H₁₆N₄·CH₄O, the aniline ring forms dihedral angles of 89.9 (2) and 85.4 (2)° with the benzimidazole and benzene rings, respectively. The orientation of the aniline ring is mainly determined by strong hydrogen bonds between the amino group and the non-fused quinazoline N atom. Intermolecular hydrogen bonds of the N—H⋯N—H⋯N type along [010] and the N—H⋯O—H⋯N type along [100] are formed, resulting in C₂²(4) and C²₂(10) descriptors, respectively, on a binary level of graph-set analysis. There are C—H⋯π contacts with H⋯π distances of 2.44 Å; however, no π-stacking is observed.

Related literature

For the synthesis of quinazolines, see: Kubicova et al. (2003 ); Niementowski (1895 ). For the conformation, see: Cuny et al. (1980 ); Williamson (1957 ).

Experimental

Crystal data

C₂₀H₁₆N₄·CH₄O
M_r = 344.41
Monoclinic, P 2₁ /c
a = 9.3703 (2) Å
b = 5.1728 (1) Å
c = 35.5169 (9) Å
β = 91.3908 (14)°
V = 1721.02 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 200 K
0.23 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
9302 measured reflections
3136 independent reflections
2089 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.123
S = 1.08
3136 reflections
253 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3a⋯N4ⁱ	0.93 (2)	2.13 (2)	3.058 (3)	174.5 (18)
N4—H4a⋯O1ⁱⁱ	0.95 (2)	2.00 (3)	2.946 (3)	174.4 (19)
N4—H4b⋯N3	0.86 (2)	2.35 (2)	3.006 (3)	133.8 (19)
O1—H1⋯N1	0.95 (3)	1.88 (3)	2.814 (2)	167 (3)
C14—H14⋯Cgⁱ	1.00	2.44	3.408 (2)	162
Symmetry codes: (i) x, y-1, z; (ii) x+1, y, z. Cg is the centroid of the C1–C6 ring.

Data collection: COLLECT (Nonius, 2004 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) 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 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PARST (Nardelli, 1995 ), publCIF (Westrip, 2008 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021886/bg2264sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021886/bg2264Isup2.hkl

checkCIF report

Comment top

In the present work the structure of 2-(2,3,5,6-tetrahydrobenzimidazo[1,2-c]quinazolin-5-yl)benzenamine (Figure 1) has been determined to explore its suitability as a bidentate ligand for various metal ions. In the structure the quinazoline ring adopts a chair conformation: atoms C7, C8, C13, N2 and N3 are coplanar, with atom C14 departing from the plane by 0.2391 Å . The orientation of the aniline ring is mainly determined by a series of hydrogen-bonds between NH₂ and NH groups, and between the phenylamino group and the quinazoline nitrogen (Figure 1 and Table 1). This ring makes dihedral angles of 89.9 (2)° and 85.4 (2)° with the benzimidazole and phenyl rings respectively. The ligand bond distances and angles show that N1—C7 is a localized double bond [1.321 (3) Å], with N2—C7 a single bond at 1.383 (3) Å. The N3—C14 bond length is 1.459 (3) Å, and the N3—C14—N2 bond angle [108.14 (17)°] illustrates the sp³ hybridization of C14. All the other bond lengths and angles in the molecule are normal.

Intermolecular hydrogen bonds of the N–H···N–H···N type along [010] and N–H···O–H···N along [100] are formed (Table 1) resulting in a C²₂(4) descriptor and a C²₂(10) descriptor on a binary level of graph set analysis, respectively. C–H···π contacts with H···Cg distances of 2.44 Å are presnt in the structure (Cg is the centre of gravity of ring C1 – C6); however, no π-stacking is observed.

Related literature top

For the synthesis of quinazolines, see: Kubicova et al. (2003); Niementowski (1895). For the conformation, see: Cuny et al. (1980); Williamson (1957). Cg is the centroid of the C1–C6 ring.

Experimental top

All chemicals used (reagent grade) were commercially available. A mass of 1.22 g (0.010 mol) of 2-aminobenzaldehyde was dissolved in methanol (50 cm³), and 2.09 g (0.010 mol) of 2-(2-aminophenyl)-1-benzimidazole was added with stirring. The mixture was heated under reflux for 2 h, then cooled to room temperature and filtered. The volume of the solution was reduced to ~ 10 cm³, and left to evaporate slowly at room temperature. After 2 days 2.48 g (72%) of colourless crystals, with the formulation C₂₀H₁₆N₄.CH₄O and suitable for X-ray analysis, were collected. M.p. 211°C. ¹H NMR (300 MHz, d₆-DMSO): 7.97 (1H,d), 7.62 (1H, d), 7.27 (1H, d), 7.25 (1H,t), 7.13 (2H, t), 6.97–7.02 (2H, m), 6.94 (1H, t), 6.86 (1H, t), 6.78 (1H, d), 6.61 (1H, d), 6.54(1H, t), 5.45 (2H, s), 3.18 (3H, s).

Computing details top

Data collection: COLLECT (Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: 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) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PARST (Nardelli, 1995), publCIF (Westrip, 2008) and WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title compound (anisotropic displacement ellipsoids drawn at the 50% probability level). Hydrogen bonds determining the conformational arrangement of the analine rings are also shown. Symmetry codes: (i): x, y+1, z; (ii) x+1, y, z.

2-(5,6-Dihydrobenzimidazolo[1,2-c]quinazolin-6-yl)aniline methanol solvate top

Crystal data top

C₂₀H₁₆N₄·CH₄O	F(000) = 728
M_r = 344.41	D_x = 1.329 (1) Mg m⁻³
Monoclinic, P2₁/c	Melting point: 484 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.3703 (2) Å	Cell parameters from 41046 reflections
b = 5.1728 (1) Å	θ = 3.1–25.4°
c = 35.5169 (9) Å	µ = 0.09 mm⁻¹
β = 91.3908 (14)°	T = 200 K
V = 1721.02 (7) Å³	Rod, yellow
Z = 4	0.23 × 0.06 × 0.05 mm

Data collection top

Nonius KappaCCD diffractometer	2089 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.051
MONTEL, graded multilayered X-ray optics monochromator	θ_max = 25.4°, θ_min = 3.2°
Detector resolution: 9 pixels mm^-1	h = −11→11
CCD; rotation images, ϕ and ω scans	k = −5→6
9302 measured reflections	l = −42→42
3136 independent reflections

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0417P)² + 0.5855P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
3136 reflections	Δρ_max = 0.19 e Å⁻³
253 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0138 (19)

Crystal data top

C₂₀H₁₆N₄·CH₄O	V = 1721.02 (7) Å³
M_r = 344.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.3703 (2) Å	µ = 0.09 mm⁻¹
b = 5.1728 (1) Å	T = 200 K
c = 35.5169 (9) Å	0.23 × 0.06 × 0.05 mm
β = 91.3908 (14)°

Data collection top

Nonius KappaCCD diffractometer	2089 reflections with I > 2σ(I)
9302 measured reflections	R_int = 0.051
3136 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.19 e Å⁻³
3136 reflections	Δρ_min = −0.20 e Å⁻³
253 parameters

Special details top

Refinement. N- and O-bonded H: All H-atom parameters refined C-bonded H: H-atom parameters constrained

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

	x	y	z	U_iso*/U_eq
O1	−0.05660 (18)	0.5134 (3)	0.32314 (5)	0.0506 (5)
H1	0.038 (3)	0.482 (5)	0.3324 (8)	0.087 (10)*
N1	0.20470 (18)	0.3599 (3)	0.35685 (5)	0.0349 (5)
N2	0.38507 (17)	0.1319 (3)	0.38325 (5)	0.0321 (5)
N3	0.5138 (2)	−0.1946 (4)	0.35148 (5)	0.0407 (5)
H3a	0.564 (2)	−0.350 (5)	0.3544 (6)	0.043 (7)*
N4	0.6823 (2)	0.2995 (4)	0.35560 (6)	0.0381 (5)
H4a	0.764 (3)	0.364 (4)	0.3436 (6)	0.051 (7)*
H4b	0.635 (2)	0.195 (4)	0.3412 (6)	0.040 (7)*
C1	0.2283 (2)	0.4419 (4)	0.39363 (6)	0.0329 (5)
C2	0.1591 (2)	0.6363 (4)	0.41352 (6)	0.0394 (6)
H2	0.0863	0.7387	0.4019	0.047*
C3	0.2005 (2)	0.6737 (5)	0.45063 (7)	0.0437 (6)
H3	0.1545	0.8037	0.4648	0.052*
C4	0.3083 (3)	0.5254 (5)	0.46794 (6)	0.0443 (6)
H4	0.3332	0.5557	0.4937	0.053*
C5	0.3792 (2)	0.3361 (4)	0.44846 (6)	0.0393 (6)
H5	0.4528	0.2360	0.4601	0.047*
C6	0.3383 (2)	0.2981 (4)	0.41099 (6)	0.0317 (5)
C7	0.2981 (2)	0.1726 (4)	0.35178 (6)	0.0307 (5)
C8	0.3146 (2)	0.0110 (4)	0.31914 (6)	0.0321 (5)
C9	0.2270 (2)	0.0334 (5)	0.28675 (6)	0.0410 (6)
H9	0.1572	0.1664	0.2853	0.049*
C10	0.2408 (3)	−0.1347 (5)	0.25705 (6)	0.0475 (7)
H10	0.1800	−0.1208	0.2354	0.057*
C11	0.3452 (3)	−0.3251 (5)	0.25931 (6)	0.0452 (6)
H11	0.3552	−0.4419	0.2389	0.054*
C12	0.4343 (2)	−0.3483 (4)	0.29040 (6)	0.0393 (6)
H12	0.5060	−0.4781	0.2912	0.047*
C13	0.4193 (2)	−0.1808 (4)	0.32092 (6)	0.0333 (5)
C14	0.4874 (2)	−0.0827 (4)	0.38838 (6)	0.0342 (5)
H14	0.4431	−0.2178	0.4045	0.041*
C15	0.6265 (2)	0.0014 (4)	0.40688 (6)	0.0322 (5)
C16	0.7166 (2)	0.1831 (4)	0.39045 (6)	0.0337 (5)
C17	0.8413 (2)	0.2541 (5)	0.40991 (7)	0.0423 (6)
H17	0.9013	0.3825	0.3996	0.051*
C18	0.8792 (3)	0.1423 (5)	0.44374 (7)	0.0478 (7)
H18	0.9647	0.1948	0.4565	0.057*
C19	0.7947 (3)	−0.0451 (5)	0.45936 (7)	0.0469 (6)
H19	0.8225	−0.1265	0.4824	0.056*
C20	0.6682 (2)	−0.1127 (4)	0.44085 (6)	0.0408 (6)
H20	0.6086	−0.2400	0.4516	0.049*
C21	−0.0816 (3)	0.7792 (5)	0.32160 (8)	0.0677 (8)
H21A	−0.0188	0.8671	0.3400	0.102*
H21B	−0.1814	0.8141	0.3275	0.102*
H21C	−0.0623	0.8430	0.2962	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0392 (11)	0.0532 (12)	0.0589 (11)	0.0000 (9)	−0.0085 (8)	0.0070 (9)
N1	0.0293 (10)	0.0331 (11)	0.0421 (12)	0.0012 (9)	−0.0009 (8)	−0.0012 (9)
N2	0.0292 (10)	0.0293 (10)	0.0378 (11)	0.0002 (8)	−0.0033 (8)	−0.0017 (8)
N3	0.0379 (12)	0.0347 (12)	0.0491 (13)	0.0077 (10)	−0.0095 (9)	−0.0094 (9)
N4	0.0321 (12)	0.0386 (12)	0.0435 (13)	−0.0024 (10)	0.0001 (10)	0.0054 (10)
C1	0.0268 (12)	0.0324 (13)	0.0395 (13)	−0.0056 (10)	0.0006 (10)	0.0001 (10)
C2	0.0307 (13)	0.0357 (14)	0.0519 (15)	0.0003 (11)	−0.0005 (11)	−0.0032 (11)
C3	0.0395 (14)	0.0424 (15)	0.0494 (15)	−0.0006 (12)	0.0058 (11)	−0.0098 (12)
C4	0.0479 (15)	0.0436 (15)	0.0415 (14)	−0.0049 (13)	0.0014 (11)	−0.0057 (12)
C5	0.0403 (14)	0.0372 (14)	0.0401 (14)	−0.0034 (11)	−0.0028 (11)	−0.0009 (11)
C6	0.0306 (12)	0.0249 (12)	0.0397 (13)	−0.0049 (10)	0.0021 (10)	−0.0008 (10)
C7	0.0241 (12)	0.0301 (13)	0.0379 (13)	−0.0050 (10)	−0.0010 (9)	0.0018 (10)
C8	0.0302 (12)	0.0301 (13)	0.0360 (13)	−0.0063 (10)	0.0022 (10)	0.0023 (10)
C9	0.0403 (14)	0.0437 (15)	0.0388 (14)	0.0016 (11)	−0.0015 (11)	0.0033 (11)
C10	0.0545 (17)	0.0534 (17)	0.0344 (14)	0.0004 (13)	−0.0033 (11)	−0.0003 (12)
C11	0.0562 (16)	0.0419 (15)	0.0379 (14)	−0.0036 (13)	0.0077 (12)	−0.0035 (11)
C12	0.0425 (14)	0.0323 (14)	0.0433 (14)	0.0001 (11)	0.0058 (11)	0.0002 (11)
C13	0.0327 (13)	0.0290 (13)	0.0382 (13)	−0.0061 (10)	0.0016 (10)	0.0028 (10)
C14	0.0314 (13)	0.0280 (12)	0.0432 (13)	0.0016 (10)	−0.0025 (10)	0.0012 (10)
C15	0.0306 (12)	0.0286 (12)	0.0372 (13)	0.0003 (10)	−0.0019 (9)	−0.0004 (10)
C16	0.0302 (12)	0.0287 (13)	0.0421 (13)	0.0040 (10)	−0.0001 (10)	−0.0001 (10)
C17	0.0317 (13)	0.0411 (14)	0.0539 (15)	−0.0051 (11)	−0.0012 (11)	0.0024 (12)
C18	0.0367 (14)	0.0506 (16)	0.0554 (16)	−0.0008 (12)	−0.0142 (12)	−0.0053 (13)
C19	0.0464 (15)	0.0485 (16)	0.0451 (14)	0.0009 (13)	−0.0114 (12)	0.0031 (12)
C20	0.0363 (13)	0.0398 (14)	0.0460 (14)	−0.0013 (11)	−0.0025 (11)	0.0054 (11)
C21	0.0489 (17)	0.055 (2)	0.100 (2)	−0.0015 (14)	0.0074 (15)	0.0046 (16)

Geometric parameters (Å, º) top

O1—C21	1.395 (3)	C8—C9	1.402 (3)
O1—H1	0.95 (3)	C9—C10	1.376 (3)
N1—C7	1.320 (3)	C9—H9	0.9500
N1—C1	1.386 (3)	C10—C11	1.389 (3)
N2—C7	1.384 (3)	C10—H10	0.9500
N2—C6	1.387 (3)	C11—C12	1.373 (3)
N2—C14	1.475 (3)	C11—H11	0.9500
N3—C13	1.386 (3)	C12—C13	1.398 (3)
N3—C14	1.459 (3)	C12—H12	0.9500
N3—H3a	0.93 (2)	C14—C15	1.509 (3)
N4—C16	1.406 (3)	C14—H14	1.0000
N4—H4a	0.95 (2)	C15—C20	1.391 (3)
N4—H4b	0.86 (2)	C15—C16	1.400 (3)
C1—C2	1.397 (3)	C16—C17	1.393 (3)
C1—C6	1.402 (3)	C17—C18	1.372 (3)
C2—C3	1.379 (3)	C17—H17	0.9500
C2—H2	0.9500	C18—C19	1.377 (3)
C3—C4	1.399 (3)	C18—H18	0.9500
C3—H3	0.9500	C19—C20	1.386 (3)
C4—C5	1.379 (3)	C19—H19	0.9500
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.390 (3)	C21—H21A	0.9800
C5—H5	0.9500	C21—H21B	0.9800
C7—C8	1.441 (3)	C21—H21C	0.9800
C8—C13	1.396 (3)

C21—O1—H1	109.6 (18)	C11—C10—H10	120.6
C7—N1—C1	105.19 (17)	C12—C11—C10	121.5 (2)
C7—N2—C6	106.81 (17)	C12—C11—H11	119.3
C7—N2—C14	125.65 (17)	C10—C11—H11	119.3
C6—N2—C14	126.49 (17)	C11—C12—C13	120.0 (2)
C13—N3—C14	124.33 (19)	C11—C12—H12	120.0
C13—N3—H3a	116.1 (13)	C13—C12—H12	120.0
C14—N3—H3a	109.7 (13)	N3—C13—C8	120.48 (19)
C16—N4—H4a	112.2 (13)	N3—C13—C12	120.1 (2)
C16—N4—H4b	111.0 (15)	C8—C13—C12	119.29 (19)
H4a—N4—H4b	111 (2)	N3—C14—N2	108.15 (16)
N1—C1—C2	129.15 (19)	N3—C14—C15	110.02 (17)
N1—C1—C6	110.53 (18)	N2—C14—C15	112.88 (17)
C2—C1—C6	120.3 (2)	N3—C14—H14	108.6
C3—C2—C1	117.5 (2)	N2—C14—H14	108.6
C3—C2—H2	121.3	C15—C14—H14	108.6
C1—C2—H2	121.3	C20—C15—C16	119.16 (19)
C2—C3—C4	121.8 (2)	C20—C15—C14	118.47 (19)
C2—C3—H3	119.1	C16—C15—C14	122.33 (19)
C4—C3—H3	119.1	C17—C16—C15	118.5 (2)
C5—C4—C3	121.4 (2)	C17—C16—N4	119.7 (2)
C5—C4—H4	119.3	C15—C16—N4	121.82 (19)
C3—C4—H4	119.3	C18—C17—C16	121.3 (2)
C4—C5—C6	117.1 (2)	C18—C17—H17	119.3
C4—C5—H5	121.4	C16—C17—H17	119.3
C6—C5—H5	121.4	C17—C18—C19	120.7 (2)
N2—C6—C5	133.1 (2)	C17—C18—H18	119.7
N2—C6—C1	104.99 (17)	C19—C18—H18	119.7
C5—C6—C1	121.9 (2)	C18—C19—C20	118.7 (2)
N1—C7—N2	112.39 (18)	C18—C19—H19	120.7
N1—C7—C8	128.31 (19)	C20—C19—H19	120.7
N2—C7—C8	119.27 (19)	C19—C20—C15	121.5 (2)
C13—C8—C9	119.5 (2)	C19—C20—H20	119.2
C13—C8—C7	117.73 (18)	C15—C20—H20	119.2
C9—C8—C7	122.7 (2)	O1—C21—H21A	109.5
C10—C9—C8	120.9 (2)	O1—C21—H21B	109.5
C10—C9—H9	119.6	H21A—C21—H21B	109.5
C8—C9—H9	119.6	O1—C21—H21C	109.5
C9—C10—C11	118.9 (2)	H21A—C21—H21C	109.5
C9—C10—H10	120.6	H21B—C21—H21C	109.5

C7—N1—C1—C2	179.8 (2)	C10—C11—C12—C13	1.1 (3)
C7—N1—C1—C6	−0.4 (2)	C14—N3—C13—C8	21.6 (3)
N1—C1—C2—C3	177.9 (2)	C14—N3—C13—C12	−162.73 (19)
C6—C1—C2—C3	−1.9 (3)	C9—C8—C13—N3	175.3 (2)
C1—C2—C3—C4	0.5 (3)	C7—C8—C13—N3	−7.0 (3)
C2—C3—C4—C5	0.6 (4)	C9—C8—C13—C12	−0.4 (3)
C3—C4—C5—C6	−0.4 (3)	C7—C8—C13—C12	177.30 (18)
C7—N2—C6—C5	176.7 (2)	C11—C12—C13—N3	−176.6 (2)
C14—N2—C6—C5	8.0 (4)	C11—C12—C13—C8	−0.8 (3)
C7—N2—C6—C1	−3.1 (2)	C13—N3—C14—N2	−24.8 (3)
C14—N2—C6—C1	−171.81 (18)	C13—N3—C14—C15	−148.5 (2)
C4—C5—C6—N2	179.3 (2)	C7—N2—C14—N3	17.3 (3)
C4—C5—C6—C1	−1.0 (3)	C6—N2—C14—N3	−176.03 (18)
N1—C1—C6—N2	2.2 (2)	C7—N2—C14—C15	139.21 (19)
C2—C1—C6—N2	−178.01 (19)	C6—N2—C14—C15	−54.1 (3)
N1—C1—C6—C5	−177.61 (18)	N3—C14—C15—C20	−118.8 (2)
C2—C1—C6—C5	2.2 (3)	N2—C14—C15—C20	120.3 (2)
C1—N1—C7—N2	−1.7 (2)	N3—C14—C15—C16	59.1 (3)
C1—N1—C7—C8	176.36 (19)	N2—C14—C15—C16	−61.8 (3)
C6—N2—C7—N1	3.1 (2)	C20—C15—C16—C17	−3.7 (3)
C14—N2—C7—N1	171.95 (18)	C14—C15—C16—C17	178.5 (2)
C6—N2—C7—C8	−175.15 (17)	C20—C15—C16—N4	178.1 (2)
C14—N2—C7—C8	−6.3 (3)	C14—C15—C16—N4	0.3 (3)
N1—C7—C8—C13	−178.1 (2)	C15—C16—C17—C18	2.6 (3)
N2—C7—C8—C13	−0.2 (3)	N4—C16—C17—C18	−179.1 (2)
N1—C7—C8—C9	−0.5 (3)	C16—C17—C18—C19	0.3 (4)
N2—C7—C8—C9	177.44 (19)	C17—C18—C19—C20	−2.1 (4)
C13—C8—C9—C10	1.4 (3)	C18—C19—C20—C15	0.9 (4)
C7—C8—C9—C10	−176.1 (2)	C16—C15—C20—C19	2.0 (3)
C8—C9—C10—C11	−1.2 (3)	C14—C15—C20—C19	179.9 (2)
C9—C10—C11—C12	0.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3a···N4ⁱ	0.93 (2)	2.13 (2)	3.058 (3)	174.5 (18)
N4—H4a···O1ⁱⁱ	0.95 (2)	2.00 (3)	2.946 (3)	174.4 (19)
N4—H4b···N3	0.86 (2)	2.35 (2)	3.006 (3)	133.8 (19)
O1—H1···N1	0.95 (3)	1.88 (3)	2.814 (2)	167 (3)
C14—H14···Cgⁱ	1.00	2.44	3.408 (2)	162

Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₄·CH₄O
M_r	344.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	9.3703 (2), 5.1728 (1), 35.5169 (9)
β (°)	91.3908 (14)
V (Å³)	1721.02 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.06 × 0.05

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9302, 3136, 2089
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.123, 1.08
No. of reflections	3136
No. of parameters	253
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: COLLECT (Nonius, 2004), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), PARST (Nardelli, 1995), publCIF (Westrip, 2008) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3a···N4ⁱ	0.93 (2)	2.13 (2)	3.058 (3)	174.5 (18)
N4—H4a···O1ⁱⁱ	0.95 (2)	2.00 (3)	2.946 (3)	174.4 (19)
N4—H4b···N3	0.86 (2)	2.35 (2)	3.006 (3)	133.8 (19)
O1—H1···N1	0.95 (3)	1.88 (3)	2.814 (2)	167 (3)
C14—H14···Cgⁱ	1.00	2.44	3.408 (2)	162

Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z.

Acknowledgements

The authors thank Professor P. Klüfers for generous allocation of diffractometer time.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Cuny, E., Lichtenthaler, F. W. & Moser, A. (1980). Tetrahedron Lett. 21, 3029–3032. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kubicova, L., Sustr, M., Kralova, K., Chobnot, V., Vytlacilova, J., Jahodar, L., Vuorela, P., Machacek, M. & Kaustova, J. (2003). Molecules, 8, 756–769. Web of Science CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Niementowski, S. (1895). J. Prakt. Chem. 51, 546–566. Google Scholar
Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
Williamson, T. A. (1957). Heterocycl. Compd, 6, 331–339. Google Scholar