2-Amino-4-(4-chloro­phenyl­thio)-5-phenyl-6-(1-piperidyl)­pyrimidine

The structure of the title compound, C₂₁H₂₁ClN₄S, comprises a fully substituted pyrimidine ring that packs in a 2-amino­pyrimidine-type hydrogen-bonded polymer chain. However, hindrance from the chloro­phenyl­thio group, in turn altered by the presence of the phenyl ring, creates a convoluted hydrogen-bonded chain. The dihedral angle between the thio­phenyl and pyrimidine rings is 70.10 (7)°, while the dihedral angle between the phenyl and pyrimidine rings is 56.14 (8)°. Neither the S nor the Cl atoms is involved in the hydrogen-bonding network.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.124
• Data-to-parameter ratio = 13.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.105


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

We recently discussed the occurrence of N—H···S hydrogen-bonding associations in a series of nine 2-amino-4-sulfur-substituted pyrimidines (Lynch et al., 2002). In the packing motifs of the ten structures studied (one compound had two polymorphs), all displayed R₂²(8) hydrogen-bonded 2-aminopyrimidine dimers, to varying degrees of polymerization, whereas six packing modes additionally included N—H···S interactions, the majority being three-centre with an N—H···N interaction. The title compound, (I), prepared by the sequential addition of piperidine and 4-chlorothiophenol to 2-amino-5-phenylpyrimidine, has the appropriate S-substituent to be compared with these previously studied pyrimidine structures. In (I), the presence of the 5-phenyl ring prevents the thiophenyl group from taking on a similar conformation as in 2-amino-4-(4-chlorophenylthio)-6-morpholinopyrimidine, in which the direction of the thiophenyl group opposes that of the pyrimidine N atoms. Instead, the thiophenyl group adopts a conformation that turns it towards the heterocyclic N atoms (Fig. 1). The dihedral angle between the 5-phenyl and pyrimidine rings is 56.14 (8)°, while the dihedral angle for the thiophenyl and pyrimidine rings is 70.10 (7)°. Previously reported 2-amino-5-phenylpyrimidine-type structures, and their dihedral angle between the 5-phenyl and pyrimidine rings, are 2,4-diamino-5-(3',4'-dichlorophenyl)-6-methylpyrimidinium ethanesulfonate [71.7 (1)°; Cody, 1983], 2,4-diamino-5-(3',4'-dichlorophenyl)-6-methylpyrimidine [78.2 (5) and 88.4 (5)°; De et al., 1989] and methylbenzoprim [75.4 (2) and 73.5 (2)°; Denny et al., 1992]. The latter two compounds have two unique molecules in the asymmetric unit.

Hindrance from the 5-phenyl ring to neighbouring molecules and the conformation of the thiophenyl ring not only prevent any hydrogen-bonding associations to the S atom, but the latter also causes the resultant 2-aminopyrimidine hydrogen-bonded polymer chain to be convoluted (Fig. 2), similar to the packing of both 2-amino-4-chloro-6-(4-fluorophenylthio)pyrimidine and 2-amino-4-[4-(2,3-dimethylphenyl)piperazino]-6-phenylthiopyrimidine (Lynch et al., 2002). However, the hydrogen-bonding pattern for (I) (Table 1) does differ from these two aforementioned structures in that there is a three-centre association from one 2-amino H atom to both the adjacent pyrimidine N atom and the adjacent 2-amino N atom. This is due to the high angle (ca 90°) in which the 2-aminopyrimidines approach each other to form the hydrogen-bonded chain thus allowing one 2-amino H atom closer to both N atoms and not just the pyrimidine N. Such a high angle of incidence is due to hindrance from both the thiophenyl and piperidyl substituents because in lesser-substituted 2-aminopyrimidines any resultant hydrogen-bonded chains have a high occurrence of being essentially planar. In this respect, it is surprising that the packing network of (I) displays any R₂²(8) dimers, let alone a full chain, especially when the Cl atom is available for hydrogen-bonding associations in an unhindered position [compare this with the structure of 2-amino-4-(4-(2-ethoxyphenyl)piperazino)-6-(4-chlorophenylthio)pyrimidine in Lynch et al. (2002)].

S2. Experimental

The title compound was obtained from Key Organics Ltd and crystals were grown from ethanol solution.

S3. Refinement

All H atoms were included in the refinement, at calculated positions, as riding models, with C—H set at 0.95 (Ar—H) and 0.99 Å (CH₂), while the isotropic displacement parameters were set equal to 1.25U_eq of the preceeding normal atom except for the 2-amino H atoms, which were located on difference syntheses and for which both positional and displacement parameters refined. An R_int value of 0.105 was the result of weak high-angle data.

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular configuration and atom-numbering scheme for the title compound, showing ellipsoids at the 50% probability level.
	Fig. 2. Partial packing diagram for the title compound, showing the convoluted 2-aminopyrimidine hydrogen-bonded chain.

2-Amino-4-(4-chlorophenylthio)-5-phenyl-6-(1-piperidyl)pyrimidine

Crystal data

C21H21ClN4S	Dx = 1.351 Mg m^−3
Mr = 396.93	Melting point: 461-463 K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.645 (3) Å	Cell parameters from 9868 reflections
b = 6.4302 (13) Å	θ = 2.9–27.5°
c = 20.954 (4) Å	µ = 0.32 mm^−1
β = 98.67 (3)°	T = 120 K
V = 1950.8 (7) Å^3	Plate, colourless
Z = 4	0.40 × 0.12 × 0.02 mm
F(000) = 832

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	3422 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2637 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.105
Detector resolution: 9.091 pixels mm^-1	θmax = 25.0°, θmin = 3.2°
ϕ and ω scans	h = −17→16
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −7→7
Tmin = 0.884, Tmax = 0.994	l = −24→24
14972 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0616P)^2 + 0.0316P] where P = (Fo^2 + 2Fc^2)/3
3422 reflections	(Δ/σ)max < 0.001
252 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Special details

Geometry. Mean plane data ex SHELXL97 for molecule (I) ############################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 11.9374 (0.0104) x − 1.3699 (0.0065) y + 13.7333 (0.0171) z = 1.8469 (0.0113)

* 0.0089 (0.0016) C51 * −0.0072 (0.0016) C52 * 0.0001 (0.0017) C53 * 0.0054 (0.0018) C54 * −0.0036 (0.0018) C55 * −0.0035 (0.0017) C56

Rms deviation of fitted atoms = 0.0056

− 7.7124 (0.0118) x + 4.3870 (0.0044) y + 12.1687 (0.0154) z = 5.5470 (0.0059)

Angle to previous plane (with approximate e.s.d.) = 56.14 (0.08)

* 0.0177 (0.0014) N1 * 0.0091 (0.0015) C2 * −0.0246 (0.0013) N3 * 0.0144 (0.0014) C4 * 0.0115 (0.0014) C5 * −0.0282 (0.0014) C6

Rms deviation of fitted atoms = 0.0189

− 2.0317 (0.0134) x − 1.9801 (0.0061) y + 19.9358 (0.0122) z = 8.2404 (0.0054)

Angle to previous plane (with approximate e.s.d.) = 70.10 (0.07)

* −0.0041 (0.0015) C41 * −0.0002 (0.0016) C42 * 0.0039 (0.0016) C43 * −0.0032 (0.0017) C44 * −0.0013 (0.0017) C45 * 0.0049 (0.0017) C46

Rms deviation of fitted atoms = 0.0034

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

	x	y	z	Uiso*/Ueq
N1	0.14042 (13)	0.7168 (3)	0.28787 (9)	0.0198 (4)
C2	0.07163 (16)	0.5807 (3)	0.29266 (11)	0.0189 (5)
N21	−0.00284 (14)	0.5865 (3)	0.24671 (10)	0.0240 (5)
H21	−0.051 (2)	0.476 (4)	0.2458 (13)	0.046 (8)*
H22	−0.0060 (17)	0.671 (4)	0.2138 (13)	0.025 (7)*
N3	0.07005 (12)	0.4394 (3)	0.33982 (9)	0.0178 (4)
C4	0.14173 (15)	0.4429 (3)	0.38718 (10)	0.0162 (5)
C5	0.21829 (15)	0.5731 (3)	0.38854 (10)	0.0180 (5)
C6	0.21426 (16)	0.7077 (3)	0.33419 (11)	0.0178 (5)
S4	0.13523 (4)	0.27665 (9)	0.45470 (3)	0.02177 (19)
C41	0.02631 (16)	0.1556 (3)	0.43127 (10)	0.0198 (5)
C42	0.02266 (17)	−0.0500 (3)	0.41067 (11)	0.0232 (6)
H42	0.0784	−0.1241	0.4090	0.029*
C43	−0.06106 (17)	−0.1474 (4)	0.39268 (11)	0.0260 (6)
H43	−0.0634	−0.2882	0.3788	0.033*
C44	−0.14108 (17)	−0.0380 (4)	0.39503 (11)	0.0267 (6)
Cl4	−0.24680 (5)	−0.16362 (12)	0.37349 (4)	0.0460 (2)
C45	−0.13980 (17)	0.1676 (4)	0.41568 (12)	0.0284 (6)
H45	−0.1958	0.2409	0.4171	0.035*
C46	−0.05564 (17)	0.2630 (4)	0.43404 (12)	0.0241 (6)
H46	−0.0535	0.4030	0.4487	0.030*
C51	0.29093 (15)	0.5852 (3)	0.44639 (10)	0.0189 (5)
C52	0.34052 (16)	0.4095 (4)	0.47079 (11)	0.0233 (5)
H52	0.3309	0.2809	0.4485	0.029*
C53	0.40341 (17)	0.4205 (4)	0.52708 (12)	0.0324 (6)
H53	0.4360	0.2993	0.5434	0.040*
C54	0.41896 (17)	0.6068 (4)	0.55958 (12)	0.0346 (7)
H54	0.4619	0.6142	0.5983	0.043*
C55	0.37173 (17)	0.7826 (4)	0.53540 (13)	0.0329 (6)
H55	0.3828	0.9113	0.5574	0.041*
C56	0.30855 (17)	0.7729 (4)	0.47952 (12)	0.0251 (6)
H56	0.2767	0.8952	0.4634	0.031*
N61	0.28692 (13)	0.8425 (3)	0.32815 (9)	0.0218 (5)
C62	0.37844 (16)	0.7465 (4)	0.32875 (12)	0.0248 (6)
H621	0.3806	0.6774	0.2868	0.031*
H622	0.3882	0.6390	0.3629	0.031*
C63	0.45467 (17)	0.9058 (4)	0.34073 (12)	0.0298 (6)
H631	0.5148	0.8381	0.3384	0.037*
H632	0.4568	0.9649	0.3846	0.037*
C64	0.43878 (18)	1.0804 (4)	0.29071 (13)	0.0341 (6)
H641	0.4863	1.1897	0.3013	0.043*
H642	0.4440	1.0248	0.2473	0.043*
C65	0.34343 (18)	1.1725 (4)	0.29070 (13)	0.0306 (6)
H651	0.3319	1.2802	0.2567	0.038*
H652	0.3409	1.2404	0.3328	0.038*
C66	0.26846 (18)	1.0067 (4)	0.27882 (12)	0.0298 (6)
H661	0.2074	1.0703	0.2808	0.037*
H662	0.2674	0.9458	0.2353	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0196 (11)	0.0188 (10)	0.0202 (11)	−0.0017 (8)	0.0005 (8)	0.0009 (8)
C2	0.0226 (13)	0.0166 (11)	0.0175 (12)	0.0011 (10)	0.0033 (10)	−0.0027 (9)
N21	0.0262 (12)	0.0231 (11)	0.0205 (12)	−0.0035 (9)	−0.0035 (9)	0.0037 (9)
N3	0.0198 (11)	0.0170 (10)	0.0164 (10)	0.0000 (8)	0.0023 (8)	0.0003 (8)
C4	0.0182 (13)	0.0155 (11)	0.0154 (12)	0.0021 (9)	0.0043 (10)	−0.0019 (9)
C5	0.0180 (12)	0.0178 (11)	0.0183 (12)	0.0020 (9)	0.0030 (10)	0.0002 (9)
C6	0.0168 (13)	0.0157 (11)	0.0210 (13)	0.0008 (9)	0.0027 (10)	−0.0011 (9)
S4	0.0201 (4)	0.0257 (3)	0.0189 (3)	−0.0032 (2)	0.0012 (3)	0.0057 (2)
C41	0.0218 (13)	0.0256 (13)	0.0121 (12)	−0.0041 (10)	0.0035 (10)	0.0038 (9)
C42	0.0269 (14)	0.0218 (13)	0.0224 (13)	0.0002 (10)	0.0087 (11)	0.0021 (10)
C43	0.0344 (16)	0.0253 (13)	0.0194 (13)	−0.0049 (11)	0.0076 (11)	−0.0029 (10)
C44	0.0248 (14)	0.0374 (15)	0.0183 (13)	−0.0119 (11)	0.0048 (10)	−0.0015 (11)
Cl4	0.0312 (4)	0.0638 (5)	0.0427 (5)	−0.0213 (3)	0.0050 (3)	−0.0146 (4)
C45	0.0210 (15)	0.0371 (15)	0.0279 (14)	0.0020 (11)	0.0062 (11)	0.0015 (11)
C46	0.0261 (15)	0.0228 (13)	0.0248 (14)	0.0001 (10)	0.0081 (11)	0.0010 (10)
C51	0.0136 (12)	0.0252 (12)	0.0185 (12)	−0.0021 (10)	0.0038 (9)	0.0017 (10)
C52	0.0205 (13)	0.0260 (12)	0.0236 (13)	−0.0028 (10)	0.0038 (10)	0.0042 (10)
C53	0.0205 (14)	0.0441 (16)	0.0316 (15)	0.0029 (12)	0.0010 (12)	0.0140 (13)
C54	0.0225 (15)	0.0568 (18)	0.0219 (14)	−0.0034 (13)	−0.0046 (11)	−0.0011 (13)
C55	0.0223 (15)	0.0425 (15)	0.0332 (15)	−0.0071 (12)	0.0015 (12)	−0.0139 (13)
C56	0.0225 (14)	0.0273 (13)	0.0263 (14)	−0.0020 (10)	0.0060 (11)	−0.0017 (11)
N61	0.0200 (11)	0.0202 (10)	0.0244 (11)	−0.0014 (8)	0.0010 (9)	0.0058 (8)
C62	0.0236 (15)	0.0265 (13)	0.0252 (14)	0.0001 (10)	0.0064 (11)	0.0031 (10)
C63	0.0238 (14)	0.0351 (14)	0.0308 (14)	−0.0040 (11)	0.0056 (11)	0.0007 (12)
C64	0.0373 (17)	0.0370 (14)	0.0288 (14)	−0.0169 (13)	0.0073 (12)	−0.0022 (12)
C65	0.0387 (17)	0.0252 (13)	0.0271 (14)	−0.0052 (11)	0.0029 (12)	0.0077 (11)
C66	0.0316 (15)	0.0249 (13)	0.0311 (15)	−0.0035 (11)	−0.0010 (12)	0.0112 (11)

Geometric parameters (Å, º)

N1—C6	1.341 (3)	C52—C53	1.385 (3)
N1—C2	1.350 (3)	C52—H52	0.95
C2—N21	1.342 (3)	C53—C54	1.380 (4)
C2—N3	1.345 (3)	C53—H53	0.95
N21—H21	1.00 (3)	C54—C55	1.381 (4)
N21—H22	0.88 (3)	C54—H54	0.95
N3—C4	1.332 (3)	C55—C56	1.380 (4)
C4—C5	1.396 (3)	C55—H55	0.95
C4—S4	1.787 (2)	C56—H56	0.95
C5—C6	1.425 (3)	N61—C66	1.474 (3)
C5—C51	1.490 (3)	N61—C62	1.474 (3)
C6—N61	1.393 (3)	C62—C63	1.508 (3)
S4—C41	1.776 (2)	C62—H621	0.99
C41—C42	1.389 (3)	C62—H622	0.99
C41—C46	1.394 (3)	C63—C64	1.530 (3)
C42—C43	1.378 (3)	C63—H631	0.99
C42—H42	0.95	C63—H632	0.99
C43—C44	1.374 (4)	C64—C65	1.517 (4)
C43—H43	0.95	C64—H641	0.99
C44—C45	1.390 (3)	C64—H642	0.99
C44—Cl4	1.744 (2)	C65—C66	1.524 (3)
C45—C46	1.379 (3)	C65—H651	0.99
C45—H45	0.95	C65—H652	0.99
C46—H46	0.95	C66—H661	0.99
C51—C56	1.397 (3)	C66—H662	0.99
C51—C52	1.398 (3)
C6—N1—C2	116.57 (19)	C52—C53—H53	119.9
N21—C2—N3	116.4 (2)	C53—C54—C55	119.6 (2)
N21—C2—N1	117.6 (2)	C53—C54—H54	120.2
N3—C2—N1	126.0 (2)	C55—C54—H54	120.2
C2—N21—H21	119.3 (16)	C56—C55—C54	120.6 (2)
C2—N21—H22	121.6 (17)	C56—C55—H55	119.7
H21—N21—H22	118 (2)	C54—C55—H55	119.7
C4—N3—C2	115.93 (18)	C55—C56—C51	120.7 (2)
N3—C4—C5	124.46 (19)	C55—C56—H56	119.7
N3—C4—S4	116.73 (16)	C51—C56—H56	119.7
C5—C4—S4	118.74 (17)	C6—N61—C66	116.59 (19)
C4—C5—C6	114.3 (2)	C6—N61—C62	116.41 (18)
C4—C5—C51	121.41 (19)	C66—N61—C62	112.12 (19)
C6—C5—C51	123.85 (19)	N61—C62—C63	111.48 (19)
N1—C6—N61	116.8 (2)	N61—C62—H621	109.3
N1—C6—C5	122.5 (2)	C63—C62—H621	109.3
N61—C6—C5	120.7 (2)	N61—C62—H622	109.3
C41—S4—C4	101.31 (11)	C63—C62—H622	109.3
C42—C41—C46	119.4 (2)	H621—C62—H622	108.0
C42—C41—S4	119.59 (18)	C62—C63—C64	110.6 (2)
C46—C41—S4	120.96 (18)	C62—C63—H631	109.5
C43—C42—C41	120.6 (2)	C64—C63—H631	109.5
C43—C42—H42	119.7	C62—C63—H632	109.5
C41—C42—H42	119.7	C64—C63—H632	109.5
C44—C43—C42	119.1 (2)	H631—C63—H632	108.1
C44—C43—H43	120.4	C65—C64—C63	109.4 (2)
C42—C43—H43	120.4	C65—C64—H641	109.8
C43—C44—C45	121.8 (2)	C63—C64—H641	109.8
C43—C44—Cl4	118.85 (19)	C65—C64—H642	109.8
C45—C44—Cl4	119.4 (2)	C63—C64—H642	109.8
C46—C45—C44	118.7 (2)	H641—C64—H642	108.2
C46—C45—H45	120.7	C64—C65—C66	111.6 (2)
C44—C45—H45	120.7	C64—C65—H651	109.3
C45—C46—C41	120.5 (2)	C66—C65—H651	109.3
C45—C46—H46	119.8	C64—C65—H652	109.3
C41—C46—H46	119.8	C66—C65—H652	109.3
C56—C51—C52	118.0 (2)	H651—C65—H652	108.0
C56—C51—C5	120.4 (2)	N61—C66—C65	109.6 (2)
C52—C51—C5	121.6 (2)	N61—C66—H661	109.8
C53—C52—C51	120.8 (2)	C65—C66—H661	109.8
C53—C52—H52	119.6	N61—C66—H662	109.8
C51—C52—H52	119.6	C65—C66—H662	109.8
C54—C53—C52	120.2 (2)	H661—C66—H662	108.2
C54—C53—H53	119.9
C6—N1—C2—N21	−179.8 (2)	C44—C45—C46—C41	0.6 (4)
C6—N1—C2—N3	0.9 (3)	C42—C41—C46—C45	−0.9 (3)
N21—C2—N3—C4	−176.21 (18)	S4—C41—C46—C45	179.94 (18)
N1—C2—N3—C4	3.2 (3)	C4—C5—C51—C56	−118.6 (2)
C2—N3—C4—C5	−3.7 (3)	C6—C5—C51—C56	53.4 (3)
C2—N3—C4—S4	173.31 (15)	C4—C5—C51—C52	58.6 (3)
N3—C4—C5—C6	0.4 (3)	C6—C5—C51—C52	−129.4 (2)
S4—C4—C5—C6	−176.55 (15)	C56—C51—C52—C53	1.7 (3)
N3—C4—C5—C51	173.1 (2)	C5—C51—C52—C53	−175.6 (2)
S4—C4—C5—C51	−3.8 (3)	C51—C52—C53—C54	−0.9 (4)
C2—N1—C6—N61	177.6 (2)	C52—C53—C54—C55	−0.3 (4)
C2—N1—C6—C5	−4.5 (3)	C53—C54—C55—C56	0.7 (4)
C4—C5—C6—N1	3.9 (3)	C54—C55—C56—C51	0.2 (4)
C51—C5—C6—N1	−168.6 (2)	C52—C51—C56—C55	−1.3 (3)
C4—C5—C6—N61	−178.32 (19)	C5—C51—C56—C55	176.0 (2)
C51—C5—C6—N61	9.2 (3)	N1—C6—N61—C66	11.1 (3)
N3—C4—S4—C41	0.55 (18)	C5—C6—N61—C66	−166.8 (2)
C5—C4—S4—C41	177.75 (17)	N1—C6—N61—C62	−124.9 (2)
C4—S4—C41—C42	105.69 (19)	C5—C6—N61—C62	57.3 (3)
C4—S4—C41—C46	−75.2 (2)	C6—N61—C62—C63	−164.0 (2)
C46—C41—C42—C43	0.4 (3)	C66—N61—C62—C63	58.1 (3)
S4—C41—C42—C43	179.58 (17)	N61—C62—C63—C64	−56.0 (3)
C41—C42—C43—C44	0.3 (3)	C62—C63—C64—C65	54.7 (3)
C42—C43—C44—C45	−0.6 (4)	C63—C64—C65—C66	−55.9 (3)
C42—C43—C44—Cl4	−178.92 (17)	C6—N61—C66—C65	164.5 (2)
C43—C44—C45—C46	0.1 (4)	C62—N61—C66—C65	−57.7 (3)
Cl4—C44—C45—C46	178.42 (18)	C64—C65—C66—N61	57.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···N1^i	1.00 (3)	2.17 (3)	3.130 (3)	160 (2)
N21—H21···N21^i	1.00 (3)	2.63 (3)	3.219 (3)	118 (2)
N21—H22···N3^ii	0.88 (3)	2.19 (3)	2.978 (3)	150 (2)

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