5-[N-(1H-Benzotriazol-1-yl­methyl)­amino]-3-tert-butyl-1-phenyl­pyrazole: sheets built from N-H...N, C-H...N and C-H...[pi](pyrazole) interactions

In the title compound, C₂₀H₂₂N₆, the mol­ecules are linked into a chain of rings by N-H...N [H...N 2.16 Å, N...N 2.950 (3) Å and N-H...N 149°] and C-H...N [H...N 2.55 Å, C...N 3.481 (3) Å and C-H...N 165°] hydrogen bonds, and these chains are linked into sheets by means of C-­H...[pi](pyrazole) interactions.

S1. Comment

The title compound, (I) (Fig. 1), was prepared as a precursor for the synthesis of new hydrogenated pyrazolopyridines using the benzotriazole methodology (Katritzky et al., 1995, 1998; Abonia et al., 2001).

The C—C bond distances (Table 1) in the fused arene ring show some evidence for bond fixation, with bonds C3—C4 and C5—C6 being somewhat shorter than the neighbouring bonds; likewise bond N2—N3 is markedly shorter than both N1—N2 and N5—N6. The pattern of the C—N distances is of interest; the two distances C7—N1 and C7—N4 involving planar three-connected N and four-connected C atoms are significantly different; likewise the two distances C1—N3 and C9—N6 involving two-connected N and planar three-connected C atoms differ significantly, consistent with the occurrence of single and double bonds, respectively. On the other hand, the three distances C2—N1, C8—N4 and C8—N5 involving two planar three-connected atoms span only a rather small range.

The supramolecular structure of (I) is determined by a combination of N—H···N and C—H···N hydrogen bonds and C—H···π(pyrazole) interactions (Table 2). The amino atom N4 at (x, y, z) acts as hydrogen-bond donor to triazole N3 at (2 - x, -0.5 + y, 0.5 - z), while N4 at (2 - x, -0.5 + y, 0.5 - z), in turn, acts as donor to N3 at (x, -1 + y, z), so producing a C(6) chain generated by the 2₁ screw axis along (1, y, 1/4). This is augmented by a fairly weak C—H···N hydrogen bond: C3 at (x, y, z) acts as donor to triazole N2 at (2 - x, -0.5 + y, 0.5 - z), producing a C(5) chain generated by the same screw axis as before, so that the resulting chain of rings running parallel to the [010] direction (Fig. 2) has the descriptor C(5) C(6)[R²₂(9)] (Bernstein et al., 1995). Two chains of this type run through each unit cell, in the domains 0.06 < z < 0.44 and 0.56 < z < 0.94, and within each domain, the adjacent chains are linked into a (001) sheet by the C—H···π(pyrazole) interactions. Atom C19 in the molecule at (x, y, z), which lies in the hydrogen-bonded chain along (1, y, 1/4), forms a short C—H···π contact (Table 2) with the centroid, Cg2, of the pyrazole ring of the molecule at (1 - x, -0.5 + y, 0.5 - z), which itself lies in the hydrogen-bonded chain along (1/2, y, 1/4) (Fig. 3). Propagation of this interaction thus links all of the [010] chains in a given domain of z into a single sheet. Two sheets run through each unit cell, but there are no direction-specific interactions between adjacent sheets.

The structure of the isomeric compound (II) (see Scheme above) has recently been reported in space group P2₁/c (Low et al., 2002). The supramolecular structure was described in terms of a single hydrogen bond, N51—H51···N43ⁱ [symmetry code: (i) x, y, 1 + z], forming C(8) chains by translation. However, re-examination of the structure of (II) in the light of the above analysis for (I), shows that there is also a short N—H···π(triazole) interaction, involving the N51—H52 bond, which does not participate in conventional hydrogen bonding, and the centroid (Cg2) of the triazole ring; H52···Cg2ⁱⁱ 2.72 Å, N51···Cg2ⁱⁱ 3.477 (2) Å and N51—H52···Cg2ⁱⁱ 146° [symmetry code: (ii) x, 0.5 - y, 0.5 + z]. This interaction produces a zigzag chain parallel to [001], generated by the c-glide plane at y = -0.25. The combination of N—H···N and N—H···π interactions thus generates a double chain, or molecular ladder (Fig. 4).

Since C—H···π interactions most frequently involve benzenoid rings as acceptors (Desiraju & Steiner, 1999; Suezawa et al., 2001), with rather few examples involving heterocycles, we have briefly investigated the occurrence of C—H···π(pyrazole) interactions by examining the structures of pyrazoles in the Cambridge Structural Database (CSD; Allen & Kennard, 1993) containing the fragment (III), namely a pyrazole ring carrying the same substituent atoms as found in (I). Nine examples were retrieved; the structures of three of these contained only C—H···π(arene) interactions, those of five others contained no C—H···π interactions at all, but the structure of the ninth [CSD refcode TIXPEV, (IV); Ramm et al., 1996], which crystallizes in space group P2₁/a with Z' = 2, displays quite short C—H···.π(pyrazole) interactions, such that the two independent molecules each form simple chains. For the type 1 molecules, the chain is generated by the a-glide plane at y = -0.25 [H···Cg1ⁱⁱⁱ 2.84 Å, C···Cg1ⁱⁱⁱ 3.645 (2) Å and C—H···Cg1ⁱⁱⁱ 127°; symmetry code: (iii) -0.5 + x, -0.5 - y, z] (Fig. 5), while for the type 2 molecules, the chain is generated by the a-glide plane at y = 0.25 [H···Cg2^iv 2.69 Å, C···Cg2^iv,3.537 (2) Å and C—H···Cg2^iv 145°; symmetry code: (iv) 0.5 + x, 0.5 - y, z] (Fig. 6), where Cg1 and Cg2 represent the ring centroids of the pyrazole rings in the molecules of types 1 and 2, respectively.

S2. Experimental

A solution of 5-amino-3-tert-butyl-1-phenylpyrazole (Grandberg et al., 1962; Abonia et al., 2002) (1.00 g, 4.65 mmol) and 1-hydroxymethylbenzotriazole (Burckhalter et al., 1952) (0.70 g, 4.69 mmol) in 5 ml of ethanol was heated under reflux for 3 min. After cooling, the precipitate which formed was filtered off and washed with ethanol, giving (I) as a white solid (84% yield; m.p. 453 K; analysis, found: C 69.3, H 6.43, N 24.2%; C₂₀H₂₂N₆ requires: C 69.3, H 6.4, N 24.3%). Crystals suitable for single-crystal X-ray diffraction were grown from a solution in ethanol.

S3. Refinement

Compound (I) crystallized in the orthorhombic system; space group P2₁2₁2₁ was assigned uniquely from the systematic absences. H atoms were treated as riding, with C—H distances in the range 0.95–0.99 Å and an N—H distance of 0.88 Å. The Friedel equivalent reflections were merged prior to the final refinements, as the absolute structure could not be assigned.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures

	Fig. 1. The molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I), showing the formation of a chain of rings along [010]. Atoms marked with an asterisk (*) or hash (#) are at the symmetry positions (2 - x, -0.5 + y, 0.5 - z) and (2 - x, 0.5 + y, 0.5 - z), respectively.
	Fig. 3. Part of the crystal structure of (I), showing the linking of the [010] chains by the C—H···π(pyrazole) interaction. Atoms marked with an asterisk (*) or hash (#) are at the symmetry positions (1 - x, -0.5 + y, 0.5 - z) and (1 - x, 0.5 + y, 0.5 - z), respectively.
	Fig. 4. Stereoview of part of the crystal structure of (II), showing formation of a molecular ladder built from N—H···N and N—H···π(triazole) interactions.
	Fig. 5. Part of the crystal structure of (IV), showing the formation of a C—H···π(pyrazole) chain consisting of type 1 molecules only.
	Fig. 6. Part of the crystal structure of (IV), showing the formation of a C—H···π(pyrazole) chain consisting of type 2 molecules only.

5-[N-(Benzotriazol-1-ylmethyl)amino]-3-tert-butyl-1-phenylpyrazole

Crystal data

C20H22N6	F(000) = 736
Mr = 346.44	Dx = 1.252 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2418 reflections
a = 7.2380 (5) Å	θ = 1.9–27.4°
b = 11.9743 (9) Å	µ = 0.08 mm^−1
c = 21.2062 (16) Å	T = 120 K
V = 1837.9 (2) Å^3	Plate, colourless
Z = 4	0.30 × 0.20 × 0.07 mm

Data collection

Bruker SMART1000 CCD diffractometer	2418 independent reflections
Radiation source: fine-focus sealed X-ray tube	2200 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ϕ and ω scans	θmax = 27.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −7→9
Tmin = 0.979, Tmax = 0.995	k = −15→15
12704 measured reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0692P)^2 + 0.2514P] where P = (Fo^2 + 2Fc^2)/3
2418 reflections	(Δ/σ)max < 0.001
238 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	1.0596 (2)	0.24099 (13)	0.27065 (8)	0.0232 (4)
N2	1.0770 (3)	0.35277 (14)	0.28072 (9)	0.0277 (4)
N3	1.1066 (3)	0.40159 (15)	0.22666 (9)	0.0292 (4)
C1	1.1076 (3)	0.32159 (17)	0.18008 (10)	0.0262 (4)
C2	1.0753 (3)	0.21782 (16)	0.20807 (10)	0.0231 (4)
C3	1.0613 (3)	0.11871 (17)	0.17269 (11)	0.0297 (5)
C4	1.0815 (4)	0.1306 (2)	0.10877 (11)	0.0371 (6)
C5	1.1170 (4)	0.2350 (2)	0.07999 (12)	0.0401 (6)
C6	1.1313 (3)	0.3311 (2)	0.11493 (11)	0.0341 (5)
C7	1.0200 (3)	0.16520 (16)	0.32334 (10)	0.0233 (4)
N4	0.8337 (3)	0.12756 (14)	0.32493 (9)	0.0265 (4)
C8	0.6961 (3)	0.18721 (16)	0.35393 (9)	0.0202 (4)
N5	0.5259 (2)	0.14256 (13)	0.36389 (8)	0.0228 (4)
N6	0.4122 (3)	0.21445 (14)	0.39701 (8)	0.0239 (4)
C9	0.5151 (3)	0.30470 (15)	0.40625 (9)	0.0207 (4)
C10	0.6939 (3)	0.29314 (16)	0.38047 (9)	0.0214 (4)
C11	0.4373 (3)	0.40699 (16)	0.43919 (9)	0.0236 (4)
C12	0.4214 (4)	0.50269 (16)	0.39123 (10)	0.0293 (5)
C13	0.5717 (4)	0.4412 (2)	0.49206 (10)	0.0343 (5)
C14	0.2459 (3)	0.38334 (19)	0.46731 (11)	0.0336 (5)
C15	0.4674 (3)	0.03169 (16)	0.34969 (9)	0.0216 (4)
C16	0.4088 (3)	−0.03790 (19)	0.39807 (10)	0.0279 (5)
C17	0.3577 (3)	−0.14699 (19)	0.38388 (12)	0.0341 (5)
C18	0.3679 (3)	−0.18606 (19)	0.32264 (12)	0.0345 (5)
C19	0.4245 (3)	−0.1168 (2)	0.27497 (11)	0.0335 (5)
C20	0.4728 (3)	−0.00664 (18)	0.28800 (10)	0.0274 (5)
H3	1.0393	0.0482	0.1918	0.036*
H4	1.0713	0.0663	0.0828	0.045*
H5	1.1313	0.2387	0.0355	0.048*
H6	1.1562	0.4011	0.0956	0.041*
H71	1.1027	0.0996	0.3203	0.028*
H72	1.0481	0.2040	0.3634	0.028*
H4A	0.8058	0.0638	0.3067	0.032*
H10	0.7914	0.3463	0.3811	0.026*
H12A	0.3356	0.4812	0.3576	0.035*
H12B	0.5432	0.5181	0.3731	0.035*
H12C	0.3751	0.5698	0.4125	0.035*
H13A	0.5756	0.3825	0.5242	0.041*
H13B	0.5296	0.5112	0.5113	0.041*
H13C	0.6956	0.4518	0.4744	0.041*
H14A	0.1601	0.3629	0.4335	0.040*
H14B	0.2004	0.4503	0.4889	0.040*
H14C	0.2549	0.3217	0.4976	0.040*
H16	0.4036	−0.0114	0.4403	0.034*
H17	0.3155	−0.1950	0.4165	0.041*
H18	0.3354	−0.2612	0.3136	0.041*
H19	0.4308	−0.1441	0.2330	0.040*
H20	0.5091	0.0420	0.2548	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0228 (9)	0.0116 (7)	0.0353 (9)	−0.0020 (7)	0.0011 (8)	−0.0019 (7)
N2	0.0291 (9)	0.0114 (8)	0.0427 (10)	−0.0012 (7)	0.0004 (8)	−0.0021 (7)
N3	0.0308 (10)	0.0168 (8)	0.0399 (10)	−0.0021 (7)	0.0000 (9)	0.0029 (8)
C1	0.0216 (10)	0.0179 (9)	0.0391 (11)	−0.0018 (8)	−0.0003 (9)	0.0056 (9)
C2	0.0199 (10)	0.0168 (9)	0.0327 (10)	0.0003 (8)	0.0011 (9)	0.0020 (8)
C3	0.0320 (12)	0.0170 (9)	0.0400 (11)	−0.0006 (9)	0.0049 (10)	−0.0024 (9)
C4	0.0400 (14)	0.0320 (12)	0.0394 (12)	−0.0009 (11)	0.0033 (11)	−0.0093 (10)
C5	0.0416 (14)	0.0467 (15)	0.0320 (11)	−0.0006 (12)	0.0036 (11)	0.0017 (11)
C6	0.0323 (12)	0.0311 (11)	0.0389 (12)	−0.0024 (10)	−0.0009 (10)	0.0098 (10)
C7	0.0225 (10)	0.0164 (8)	0.0309 (10)	0.0005 (8)	0.0012 (9)	0.0006 (8)
N4	0.0250 (9)	0.0138 (7)	0.0406 (10)	−0.0024 (7)	0.0066 (8)	−0.0075 (8)
C8	0.0229 (9)	0.0152 (9)	0.0223 (8)	0.0004 (8)	0.0002 (8)	0.0011 (8)
N5	0.0223 (8)	0.0160 (8)	0.0300 (8)	0.0005 (7)	0.0021 (7)	−0.0055 (7)
N6	0.0261 (9)	0.0174 (8)	0.0284 (8)	0.0020 (7)	0.0033 (8)	−0.0047 (7)
C9	0.0283 (11)	0.0143 (8)	0.0195 (8)	0.0016 (8)	−0.0013 (8)	−0.0001 (7)
C10	0.0275 (10)	0.0134 (8)	0.0233 (9)	0.0002 (8)	−0.0008 (8)	−0.0008 (8)
C11	0.0299 (11)	0.0169 (9)	0.0241 (9)	0.0036 (8)	0.0001 (9)	−0.0033 (8)
C12	0.0370 (13)	0.0171 (9)	0.0336 (10)	0.0050 (9)	0.0023 (10)	0.0003 (8)
C13	0.0432 (14)	0.0303 (11)	0.0294 (10)	0.0029 (11)	−0.0035 (10)	−0.0112 (9)
C14	0.0366 (13)	0.0226 (11)	0.0416 (12)	0.0033 (10)	0.0119 (10)	−0.0052 (10)
C15	0.0186 (9)	0.0162 (9)	0.0301 (10)	−0.0011 (7)	−0.0006 (8)	−0.0034 (8)
C16	0.0286 (11)	0.0255 (10)	0.0297 (10)	−0.0039 (9)	0.0016 (9)	−0.0035 (8)
C17	0.0332 (12)	0.0234 (11)	0.0455 (13)	−0.0062 (10)	0.0026 (10)	0.0038 (10)
C18	0.0277 (11)	0.0208 (10)	0.0549 (14)	−0.0053 (9)	−0.0026 (11)	−0.0081 (11)
C19	0.0345 (13)	0.0298 (12)	0.0363 (11)	−0.0038 (10)	−0.0028 (10)	−0.0136 (10)
C20	0.0301 (11)	0.0241 (10)	0.0281 (10)	−0.0038 (9)	−0.0014 (9)	−0.0032 (8)

Geometric parameters (Å, º)

C1—C2	1.397 (3)	C9—C11	1.518 (3)
C2—C3	1.408 (3)	C10—H10	0.9500
C3—C4	1.371 (3)	C11—C14	1.535 (3)
C4—C5	1.415 (4)	C11—C12	1.536 (3)
C5—C6	1.373 (4)	C11—C13	1.540 (3)
C6—C1	1.397 (3)	C12—H12A	0.9800
C1—N3	1.376 (3)	C12—H12B	0.9800
C2—N1	1.361 (3)	C12—H12C	0.9800
N1—N2	1.361 (2)	C13—H13A	0.9800
N2—N3	1.305 (3)	C13—H13B	0.9800
N1—C7	1.468 (3)	C13—H13C	0.9800
C7—N4	1.422 (3)	C14—H14A	0.9800
N4—C8	1.372 (3)	C14—H14B	0.9800
C8—N5	1.359 (3)	C14—H14C	0.9800
N5—N6	1.383 (2)	C15—C20	1.387 (3)
N6—C9	1.327 (3)	C15—C16	1.388 (3)
C9—C10	1.412 (3)	C16—C17	1.390 (3)
C10—C8	1.388 (3)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.382 (4)
C4—H4	0.9500	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.370 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—H71	0.9900	C19—C20	1.393 (3)
C7—H72	0.9900	C19—H19	0.9500
N4—H4A	0.8800	C20—H20	0.9500
N5—C15	1.426 (2)
C2—N1—N2	110.23 (17)	C9—C10—H10	127.5
C2—N1—C7	129.26 (16)	C9—C11—C14	111.38 (17)
N2—N1—C7	120.44 (17)	C9—C11—C12	108.96 (15)
N3—N2—N1	108.54 (17)	C14—C11—C12	109.09 (18)
N2—N3—C1	108.65 (17)	C9—C11—C13	108.38 (18)
N3—C1—C6	130.8 (2)	C14—C11—C13	109.67 (18)
N3—C1—C2	108.26 (18)	C12—C11—C13	109.32 (18)
C6—C1—C2	120.9 (2)	C11—C12—H12A	109.5
N1—C2—C1	104.31 (17)	C11—C12—H12B	109.5
N1—C2—C3	133.29 (19)	H12A—C12—H12B	109.5
C1—C2—C3	122.39 (19)	C11—C12—H12C	109.5
C4—C3—C2	115.6 (2)	H12A—C12—H12C	109.5
C4—C3—H3	122.2	H12B—C12—H12C	109.5
C2—C3—H3	122.2	C11—C13—H13A	109.5
C3—C4—C5	122.6 (2)	C11—C13—H13B	109.5
C3—C4—H4	118.7	H13A—C13—H13B	109.5
C5—C4—H4	118.7	C11—C13—H13C	109.5
C6—C5—C4	121.4 (2)	H13A—C13—H13C	109.5
C6—C5—H5	119.3	H13B—C13—H13C	109.5
C4—C5—H5	119.3	C11—C14—H14A	109.5
C5—C6—C1	117.1 (2)	C11—C14—H14B	109.5
C5—C6—H6	121.4	H14A—C14—H14B	109.5
C1—C6—H6	121.4	C11—C14—H14C	109.5
N4—C7—N1	113.52 (18)	H14A—C14—H14C	109.5
N4—C7—H71	108.9	H14B—C14—H14C	109.5
N1—C7—H71	108.9	C20—C15—C16	120.46 (19)
N4—C7—H72	108.9	C20—C15—N5	119.93 (18)
N1—C7—H72	108.9	C16—C15—N5	119.59 (18)
H71—C7—H72	107.7	C15—C16—C17	119.0 (2)
C8—N4—C7	122.29 (17)	C15—C16—H16	120.5
C8—N4—H4A	118.9	C17—C16—H16	120.5
C7—N4—H4A	118.9	C18—C17—C16	120.5 (2)
N5—C8—N4	121.54 (17)	C18—C17—H17	119.8
N5—C8—C10	106.62 (17)	C16—C17—H17	119.8
N4—C8—C10	131.77 (19)	C19—C18—C17	120.3 (2)
C8—N5—N6	111.93 (16)	C19—C18—H18	119.9
C8—N5—C15	127.05 (16)	C17—C18—H18	119.9
N6—N5—C15	120.68 (17)	C18—C19—C20	120.1 (2)
C9—N6—N5	104.35 (17)	C18—C19—H19	119.9
N6—C9—C10	112.18 (17)	C20—C19—H19	119.9
N6—C9—C11	121.12 (19)	C15—C20—C19	119.6 (2)
C10—C9—C11	126.67 (18)	C15—C20—H20	120.2
C8—C10—C9	104.90 (18)	C19—C20—H20	120.2
C8—C10—H10	127.5
C2—N1—N2—N3	−1.1 (3)	C10—C8—N5—C15	−174.35 (19)
C7—N1—N2—N3	−178.26 (18)	C8—N5—N6—C9	1.0 (2)
N1—N2—N3—C1	0.4 (2)	C15—N5—N6—C9	174.79 (17)
N2—N3—C1—C6	179.2 (2)	N5—N6—C9—C10	−0.6 (2)
N2—N3—C1—C2	0.4 (2)	N5—N6—C9—C11	177.48 (16)
N2—N1—C2—C1	1.3 (2)	N5—C8—C10—C9	0.6 (2)
C7—N1—C2—C1	178.10 (19)	N4—C8—C10—C9	−176.5 (2)
N2—N1—C2—C3	−177.2 (2)	N6—C9—C10—C8	0.0 (2)
C7—N1—C2—C3	−0.4 (4)	C11—C9—C10—C8	−177.94 (18)
N3—C1—C2—N1	−1.0 (2)	N6—C9—C11—C14	8.7 (3)
C6—C1—C2—N1	−180.0 (2)	C10—C9—C11—C14	−173.59 (19)
N3—C1—C2—C3	177.7 (2)	N6—C9—C11—C12	−111.7 (2)
C6—C1—C2—C3	−1.3 (3)	C10—C9—C11—C12	66.0 (3)
N1—C2—C3—C4	178.3 (2)	N6—C9—C11—C13	129.4 (2)
C1—C2—C3—C4	0.0 (3)	C10—C9—C11—C13	−52.9 (3)
C2—C3—C4—C5	1.0 (4)	C8—N5—C15—C20	−60.3 (3)
C3—C4—C5—C6	−0.7 (4)	N6—N5—C15—C20	126.9 (2)
C4—C5—C6—C1	−0.6 (4)	C8—N5—C15—C16	118.4 (2)
N3—C1—C6—C5	−177.2 (2)	N6—N5—C15—C16	−54.4 (3)
C2—C1—C6—C5	1.5 (4)	C20—C15—C16—C17	0.8 (3)
C2—N1—C7—N4	−72.4 (3)	N5—C15—C16—C17	−178.0 (2)
N2—N1—C7—N4	104.2 (2)	C15—C16—C17—C18	1.0 (4)
N1—C7—N4—C8	−86.2 (3)	C16—C17—C18—C19	−1.5 (4)
C7—N4—C8—N5	−169.37 (19)	C17—C18—C19—C20	0.2 (4)
C7—N4—C8—C10	7.4 (3)	C16—C15—C20—C19	−2.1 (3)
N4—C8—N5—N6	176.44 (17)	N5—C15—C20—C19	176.7 (2)
C10—C8—N5—N6	−1.0 (2)	C18—C19—C20—C15	1.6 (4)
N4—C8—N5—C15	3.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N3^i	0.88	2.16	2.950 (3)	149
C3—H3···N2^i	0.95	2.55	3.481 (3)	165
C19—H19···Cg2^ii	0.95	2.85	3.779 (3)	167

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2.