Bis-(1-(2-aminoethyl)piperidino), (2-(2-aminoethyl)pyridino) and (1-(2-aminoethyl)pyrrolidino)-substituted dicyanoquinodimethanes: consequences of flexible ethylene spacers with heterocyclic moieties and amine functionalities

Heterocyclic building blocks possessing ethylene spacer and amine functionality such as 1-(2-aminoethyl)piperidine (1,2-AEPi), 2-(2-aminoethyl)pyridine (2,2-AEPy) and 1-(2-aminoethyl)pyrrolidine (1,2-AEPr) were reacted with tetracyanoquinodimethane (TCNQ) to give disubstituted compounds namely bis-(1-(2-aminoethyl)piperidino)dicyanoquinodimethane (1), bis-(2-(2-aminoethyl)pyridino)dicyanoquinodimethane (2) and bis-(1-(2-aminoethyl)pyrrolidino)dicyanoquinodimethane (3). Utilization of 1,2-AEPi, 2,2-AEPy and 1,2-AEPr as disubstituents on TCNQ has resulted in interesting crystal structures. Inter- and intramolecular hydrogen-bond mediated and expanded supramolecular structures were observed in the lattices of the crystals. Strong fluorescence was observed in solids and solutions. (2) showed a strong second harmonic generation (SHG) whereas (1) and (3) were found to be SHG inactive. All compounds possess good thermal stabilities.

Computing details

Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for AEPiDQ, AEPyDQ; Bruker SMART for AEPrDQ. Cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for AEPiDQ, AEPyDQ; Bruker SMART for AEPrDQ. Data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for AEPiDQ, AEPyDQ; Bruker SAINT for AEPrDQ. For all compounds, program(s) used to solve structure: SHELXL2013 (Sheldrick, 2013); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013).

(AEPiDQ)

Crystal data

C24H34N6	Z = 2
Mr = 406.57	F(000) = 440
Triclinic, P1	Dx = 1.151 Mg m^−3
a = 8.7977 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3488 (10) Å	Cell parameters from 1536 reflections
c = 13.4887 (10) Å	θ = 3.2–25.5°
α = 84.101 (7)°	µ = 0.07 mm^−1
β = 87.035 (7)°	T = 293 K
γ = 73.903 (9)°	Block, pale yellow
V = 1173.34 (19) Å^3	0.42 × 0.34 × 0.32 mm

Data collection

Xcalibur, Eos, Gemini diffractometer	4780 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2796 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→10
Tmin = 0.971, Tmax = 0.978	k = −12→11
8002 measured reflections	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.158	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.0759P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.005
4780 reflections	Δρmax = 0.25 e Å^−3
271 parameters	Δρmin = −0.16 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	−0.0374 (2)	1.0484 (2)	0.22265 (13)	0.0429 (5)
C2	0.0572 (2)	1.0010 (2)	0.13981 (14)	0.0454 (5)
H2	0.0504	1.0577	0.0811	0.054*
C3	0.1588 (2)	0.8745 (2)	0.14267 (13)	0.0450 (5)
H3	0.2183	0.8465	0.0859	0.054*
C4	0.1751 (2)	0.7862 (2)	0.22965 (13)	0.0449 (5)
C5	0.0834 (3)	0.8332 (2)	0.31276 (14)	0.0520 (6)
H5	0.0921	0.7770	0.3718	0.062*
C6	−0.0187 (3)	0.9599 (2)	0.30956 (14)	0.0511 (5)
H6	−0.0774	0.9879	0.3666	0.061*
C7	−0.1462 (2)	1.1801 (2)	0.21789 (14)	0.0486 (5)
C8	−0.2319 (3)	1.2327 (2)	0.30279 (17)	0.0582 (6)
C9	−0.1675 (3)	1.2633 (2)	0.12842 (17)	0.0592 (6)
C10	0.2735 (2)	0.6475 (2)	0.23155 (14)	0.0465 (5)
C11	0.4196 (3)	0.6444 (2)	0.38231 (14)	0.0628 (7)
H11A	0.4115	0.6025	0.4494	0.075*
H11B	0.3646	0.7397	0.3817	0.075*
C12	0.5904 (3)	0.6281 (2)	0.35371 (16)	0.0683 (7)
H12A	0.6367	0.6717	0.3997	0.082*
H12B	0.6464	0.5328	0.3594	0.082*
C13	0.5784 (3)	0.8314 (3)	0.24415 (19)	0.0787 (8)
H13A	0.6553	0.8563	0.2817	0.094*
H13B	0.4742	0.8704	0.2727	0.094*
C14	0.5851 (4)	0.8875 (3)	0.1377 (2)	0.0948 (9)
H14A	0.5680	0.9845	0.1349	0.114*
H14B	0.5012	0.8704	0.1016	0.114*
C15	0.7426 (4)	0.8250 (4)	0.0881 (2)	0.0979 (10)
H15A	0.7386	0.8537	0.0173	0.117*
H15B	0.8248	0.8551	0.1162	0.117*
C16	0.7808 (4)	0.6736 (4)	0.1037 (2)	0.1061 (11)
H16A	0.8873	0.6345	0.0787	0.127*
H16B	0.7083	0.6430	0.0662	0.127*
C17	0.7683 (3)	0.6253 (3)	0.2125 (2)	0.0867 (9)
H17A	0.7899	0.5277	0.2199	0.104*
H17B	0.8464	0.6495	0.2495	0.104*
C18	0.3939 (3)	0.4551 (2)	0.13282 (15)	0.0599 (6)
H18A	0.4900	0.4471	0.1681	0.072*
H18B	0.4209	0.4560	0.0622	0.072*
C19	0.3369 (3)	0.3329 (2)	0.16403 (15)	0.0676 (7)
H19A	0.2400	0.3410	0.1297	0.081*
H19B	0.4154	0.2535	0.1436	0.081*
C20	0.1396 (3)	0.3632 (2)	0.29706 (17)	0.0652 (6)
H20A	0.0818	0.3103	0.2673	0.078*
H20B	0.1003	0.4565	0.2698	0.078*
C21	0.1108 (3)	0.3539 (3)	0.40868 (18)	0.0798 (8)
H21A	0.1629	0.4114	0.4382	0.096*
H21B	−0.0018	0.3854	0.4234	0.096*
C22	0.1729 (4)	0.2115 (3)	0.45301 (19)	0.0865 (9)
H22A	0.1096	0.1567	0.4316	0.104*
H22B	0.1645	0.2088	0.5251	0.104*
C23	0.3432 (4)	0.1543 (3)	0.42152 (17)	0.0818 (8)
H23A	0.3769	0.0588	0.4440	0.098*
H23B	0.4088	0.1989	0.4531	0.098*
C24	0.3668 (3)	0.1724 (2)	0.30946 (16)	0.0662 (7)
H24A	0.4786	0.1407	0.2924	0.079*
H24B	0.3119	0.1187	0.2781	0.079*
N1	−0.2989 (3)	1.2740 (2)	0.37300 (17)	0.0897 (8)
N2	−0.1808 (3)	1.3275 (2)	0.05323 (15)	0.0895 (8)
N3	0.3458 (2)	0.58211 (17)	0.31300 (11)	0.0535 (5)
H3A	0.3495	0.4982	0.3258	0.064*
N4	0.6107 (2)	0.68575 (18)	0.25270 (13)	0.0565 (5)
N5	0.2814 (2)	0.58337 (17)	0.15090 (11)	0.0517 (5)
H5A	0.2143	0.6206	0.1052	0.062*
N6	0.3069 (2)	0.31415 (16)	0.27187 (11)	0.0489 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0453 (13)	0.0423 (12)	0.0450 (11)	−0.0184 (10)	0.0020 (9)	−0.0056 (9)
C2	0.0539 (13)	0.0427 (12)	0.0401 (10)	−0.0159 (10)	0.0012 (9)	−0.0006 (9)
C3	0.0506 (13)	0.0443 (12)	0.0401 (10)	−0.0143 (10)	0.0062 (9)	−0.0043 (9)
C4	0.0504 (13)	0.0415 (12)	0.0416 (11)	−0.0131 (10)	0.0037 (9)	0.0002 (9)
C5	0.0607 (15)	0.0480 (13)	0.0441 (11)	−0.0143 (12)	0.0099 (10)	0.0037 (10)
C6	0.0553 (14)	0.0502 (13)	0.0474 (12)	−0.0159 (11)	0.0124 (10)	−0.0050 (10)
C7	0.0505 (14)	0.0449 (12)	0.0492 (12)	−0.0098 (11)	−0.0005 (10)	−0.0086 (10)
C8	0.0583 (15)	0.0486 (14)	0.0655 (14)	−0.0110 (12)	0.0045 (12)	−0.0089 (12)
C9	0.0694 (16)	0.0457 (14)	0.0549 (14)	0.0024 (12)	−0.0100 (11)	−0.0161 (11)
C10	0.0563 (14)	0.0418 (12)	0.0406 (11)	−0.0155 (11)	0.0056 (9)	0.0029 (9)
C11	0.089 (2)	0.0550 (14)	0.0378 (11)	−0.0081 (13)	−0.0089 (11)	−0.0022 (10)
C12	0.081 (2)	0.0554 (15)	0.0612 (14)	−0.0013 (13)	−0.0276 (13)	−0.0082 (11)
C13	0.077 (2)	0.0580 (17)	0.0947 (19)	−0.0093 (14)	0.0126 (15)	−0.0116 (14)
C14	0.090 (2)	0.085 (2)	0.109 (2)	−0.0342 (19)	0.0106 (18)	0.0142 (17)
C15	0.093 (2)	0.130 (3)	0.094 (2)	−0.069 (2)	0.0180 (17)	−0.021 (2)
C16	0.095 (3)	0.126 (3)	0.109 (3)	−0.042 (2)	0.0354 (19)	−0.048 (2)
C17	0.066 (2)	0.077 (2)	0.114 (2)	−0.0063 (15)	0.0021 (16)	−0.0365 (17)
C18	0.0763 (17)	0.0506 (14)	0.0448 (12)	−0.0062 (12)	0.0106 (11)	−0.0049 (10)
C19	0.103 (2)	0.0474 (14)	0.0500 (13)	−0.0157 (14)	0.0006 (12)	−0.0077 (11)
C20	0.0600 (17)	0.0604 (15)	0.0749 (16)	−0.0155 (13)	−0.0120 (12)	−0.0023 (12)
C21	0.0629 (18)	0.096 (2)	0.0850 (18)	−0.0310 (17)	0.0184 (14)	−0.0136 (16)
C22	0.100 (2)	0.102 (2)	0.0688 (16)	−0.053 (2)	0.0063 (15)	0.0043 (16)
C23	0.112 (3)	0.0641 (17)	0.0661 (16)	−0.0236 (17)	−0.0220 (15)	0.0157 (13)
C24	0.0847 (19)	0.0428 (13)	0.0656 (14)	−0.0082 (13)	−0.0128 (13)	0.0005 (11)
N1	0.0970 (19)	0.0830 (17)	0.0848 (15)	−0.0157 (14)	0.0296 (14)	−0.0285 (13)
N2	0.128 (2)	0.0617 (15)	0.0560 (12)	0.0143 (14)	−0.0160 (13)	−0.0060 (11)
N3	0.0768 (14)	0.0411 (10)	0.0413 (9)	−0.0173 (10)	−0.0019 (9)	0.0055 (8)
N4	0.0536 (12)	0.0535 (12)	0.0603 (11)	−0.0072 (9)	−0.0064 (9)	−0.0133 (9)
N5	0.0640 (13)	0.0443 (10)	0.0421 (9)	−0.0082 (9)	−0.0009 (8)	−0.0010 (8)
N6	0.0566 (12)	0.0387 (10)	0.0476 (9)	−0.0074 (9)	−0.0028 (8)	−0.0013 (8)

Geometric parameters (Å, º)

C1—C6	1.399 (3)	C15—H15A	0.9700
C1—C2	1.405 (3)	C15—H15B	0.9700
C1—C7	1.429 (3)	C16—C17	1.509 (4)
C2—C3	1.363 (3)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.399 (3)	C17—N4	1.456 (3)
C3—H3	0.9300	C17—H17A	0.9700
C4—C5	1.394 (3)	C17—H17B	0.9700
C4—C10	1.455 (3)	C18—N5	1.454 (3)
C5—C6	1.366 (3)	C18—C19	1.500 (3)
C5—H5	0.9300	C18—H18A	0.9700
C6—H6	0.9300	C18—H18B	0.9700
C7—C9	1.397 (3)	C19—N6	1.468 (2)
C7—C8	1.409 (3)	C19—H19A	0.9700
C8—N1	1.146 (3)	C19—H19B	0.9700
C9—N2	1.147 (3)	C20—N6	1.452 (3)
C10—N5	1.321 (2)	C20—C21	1.511 (3)
C10—N3	1.323 (2)	C20—H20A	0.9700
C11—N3	1.460 (3)	C20—H20B	0.9700
C11—C12	1.499 (3)	C21—C22	1.495 (4)
C11—H11A	0.9700	C21—H21A	0.9700
C11—H11B	0.9700	C21—H21B	0.9700
C12—N4	1.453 (3)	C22—C23	1.507 (4)
C12—H12A	0.9700	C22—H22A	0.9700
C12—H12B	0.9700	C22—H22B	0.9700
C13—N4	1.447 (3)	C23—C24	1.514 (3)
C13—C14	1.497 (3)	C23—H23A	0.9700
C13—H13A	0.9700	C23—H23B	0.9700
C13—H13B	0.9700	C24—N6	1.461 (3)
C14—C15	1.510 (4)	C24—H24A	0.9700
C14—H14A	0.9700	C24—H24B	0.9700
C14—H14B	0.9700	N3—H3A	0.8600
C15—C16	1.504 (4)	N5—H5A	0.8600
C6—C1—C2	116.28 (19)	H16A—C16—H16B	108.0
C6—C1—C7	122.19 (17)	N4—C17—C16	110.4 (2)
C2—C1—C7	121.54 (18)	N4—C17—H17A	109.6
C3—C2—C1	122.13 (18)	C16—C17—H17A	109.6
C3—C2—H2	118.9	N4—C17—H17B	109.6
C1—C2—H2	118.9	C16—C17—H17B	109.6
C2—C3—C4	121.06 (18)	H17A—C17—H17B	108.1
C2—C3—H3	119.5	N5—C18—C19	114.91 (19)
C4—C3—H3	119.5	N5—C18—H18A	108.5
C5—C4—C3	117.21 (19)	C19—C18—H18A	108.5
C5—C4—C10	121.01 (17)	N5—C18—H18B	108.5
C3—C4—C10	121.60 (17)	C19—C18—H18B	108.5
C6—C5—C4	121.59 (19)	H18A—C18—H18B	107.5
C6—C5—H5	119.2	N6—C19—C18	113.25 (17)
C4—C5—H5	119.2	N6—C19—H19A	108.9
C5—C6—C1	121.71 (18)	C18—C19—H19A	108.9
C5—C6—H6	119.1	N6—C19—H19B	108.9
C1—C6—H6	119.1	C18—C19—H19B	108.9
C9—C7—C8	117.6 (2)	H19A—C19—H19B	107.7
C9—C7—C1	120.59 (18)	N6—C20—C21	111.23 (19)
C8—C7—C1	121.83 (18)	N6—C20—H20A	109.4
N1—C8—C7	178.6 (3)	C21—C20—H20A	109.4
N2—C9—C7	177.3 (3)	N6—C20—H20B	109.4
N5—C10—N3	119.60 (19)	C21—C20—H20B	109.4
N5—C10—C4	118.21 (18)	H20A—C20—H20B	108.0
N3—C10—C4	122.04 (18)	C22—C21—C20	110.6 (2)
N3—C11—C12	110.41 (17)	C22—C21—H21A	109.5
N3—C11—H11A	109.6	C20—C21—H21A	109.5
C12—C11—H11A	109.6	C22—C21—H21B	109.5
N3—C11—H11B	109.6	C20—C21—H21B	109.5
C12—C11—H11B	109.6	H21A—C21—H21B	108.1
H11A—C11—H11B	108.1	C21—C22—C23	110.7 (2)
N4—C12—C11	112.23 (18)	C21—C22—H22A	109.5
N4—C12—H12A	109.2	C23—C22—H22A	109.5
C11—C12—H12A	109.2	C21—C22—H22B	109.5
N4—C12—H12B	109.2	C23—C22—H22B	109.5
C11—C12—H12B	109.2	H22A—C22—H22B	108.1
H12A—C12—H12B	107.9	C22—C23—C24	111.8 (2)
N4—C13—C14	111.5 (2)	C22—C23—H23A	109.3
N4—C13—H13A	109.3	C24—C23—H23A	109.3
C14—C13—H13A	109.3	C22—C23—H23B	109.3
N4—C13—H13B	109.3	C24—C23—H23B	109.3
C14—C13—H13B	109.3	H23A—C23—H23B	107.9
H13A—C13—H13B	108.0	N6—C24—C23	110.84 (18)
C13—C14—C15	111.5 (3)	N6—C24—H24A	109.5
C13—C14—H14A	109.3	C23—C24—H24A	109.5
C15—C14—H14A	109.3	N6—C24—H24B	109.5
C13—C14—H14B	109.3	C23—C24—H24B	109.5
C15—C14—H14B	109.3	H24A—C24—H24B	108.1
H14A—C14—H14B	108.0	C10—N3—C11	123.69 (17)
C16—C15—C14	109.9 (2)	C10—N3—H3A	118.2
C16—C15—H15A	109.7	C11—N3—H3A	118.2
C14—C15—H15A	109.7	C13—N4—C12	113.35 (18)
C16—C15—H15B	109.7	C13—N4—C17	110.1 (2)
C14—C15—H15B	109.7	C12—N4—C17	111.2 (2)
H15A—C15—H15B	108.2	C10—N5—C18	125.53 (18)
C15—C16—C17	111.5 (2)	C10—N5—H5A	117.2
C15—C16—H16A	109.3	C18—N5—H5A	117.2
C17—C16—H16A	109.3	C20—N6—C24	110.12 (18)
C15—C16—H16B	109.3	C20—N6—C19	111.45 (18)
C17—C16—H16B	109.3	C24—N6—C19	110.93 (16)

(AEPyDQ)

Crystal data

C24H22N6	Dx = 1.241 Mg m^−3
Mr = 394.47	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 536 reflections
a = 8.2134 (11) Å	θ = 3.4–20.6°
b = 12.2105 (11) Å	µ = 0.08 mm^−1
c = 21.052 (3) Å	T = 293 K
V = 2111.3 (4) Å^3	Plate, pale brown
Z = 4	0.32 × 0.24 × 0.12 mm
F(000) = 832

Data collection

Xcalibur, Eos, Gemini diffractometer	4005 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2093 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −4→10
Tmin = 0.976, Tmax = 0.991	k = −9→15
5955 measured reflections	l = −26→15

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.071	w = 1/[σ^2(Fo^2) + (0.0233P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.123	(Δ/σ)max = 0.008
S = 0.95	Δρmax = 0.17 e Å^−3
4005 reflections	Δρmin = −0.18 e Å^−3
271 parameters	Absolute structure: Flack x determined using 529 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
0 restraints	Absolute structure parameter: −2.7 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.5301 (7)	0.4747 (3)	0.6105 (2)	0.0336 (12)
C2	0.4614 (7)	0.4895 (4)	0.5501 (2)	0.0392 (13)
H2	0.3496	0.4808	0.5450	0.047*
C3	0.5552 (7)	0.5165 (4)	0.4981 (2)	0.0397 (14)
H3	0.5064	0.5248	0.4585	0.048*
C4	0.7213 (7)	0.5313 (4)	0.5044 (2)	0.0337 (13)
C5	0.7932 (7)	0.5145 (3)	0.5636 (2)	0.0376 (13)
H5	0.9051	0.5224	0.5684	0.045*
C6	0.6984 (7)	0.4861 (4)	0.6151 (2)	0.0407 (14)
H6	0.7484	0.4743	0.6542	0.049*
C7	0.4280 (7)	0.4473 (4)	0.6641 (3)	0.0393 (14)
C8	0.4965 (7)	0.4215 (4)	0.7232 (3)	0.0427 (15)
C9	0.2613 (9)	0.4381 (5)	0.6582 (3)	0.0509 (17)
C10	0.8197 (7)	0.5706 (4)	0.4508 (2)	0.0342 (12)
C11	1.0455 (7)	0.6969 (4)	0.4195 (2)	0.0410 (14)
H11A	1.0741	0.7709	0.4320	0.049*
H11B	1.0042	0.6993	0.3764	0.049*
C12	1.1938 (7)	0.6258 (4)	0.4220 (3)	0.0528 (16)
H12A	1.1658	0.5537	0.4061	0.063*
H12B	1.2272	0.6178	0.4659	0.063*
C13	1.3351 (7)	0.6692 (4)	0.3842 (3)	0.0411 (13)
C14	1.3696 (8)	0.6335 (5)	0.3231 (3)	0.0588 (18)
H14	1.3029	0.5823	0.3033	0.071*
C15	1.5030 (10)	0.6747 (6)	0.2923 (3)	0.073 (2)
H15	1.5268	0.6521	0.2511	0.088*
C16	1.6006 (8)	0.7483 (5)	0.3219 (3)	0.0651 (19)
H16	1.6928	0.7761	0.3019	0.078*
C17	1.5592 (8)	0.7807 (4)	0.3820 (3)	0.0535 (16)
H17	1.6247	0.8323	0.4020	0.064*
C18	0.7317 (7)	0.4234 (4)	0.3780 (2)	0.0503 (15)
H18A	0.6318	0.4357	0.3545	0.060*
H18B	0.7045	0.3852	0.4170	0.060*
C19	0.8465 (8)	0.3534 (4)	0.3386 (3)	0.0561 (18)
H19A	0.7950	0.2833	0.3303	0.067*
H19B	0.8650	0.3890	0.2981	0.067*
C20	1.0068 (9)	0.3340 (4)	0.3703 (3)	0.0538 (18)
C21	1.1451 (11)	0.3258 (5)	0.3349 (4)	0.087 (3)
H21	1.1416	0.3349	0.2910	0.104*
C22	1.2902 (14)	0.3038 (8)	0.3652 (6)	0.126 (5)
H22	1.3855	0.2966	0.3417	0.151*
C23	1.2936 (15)	0.2928 (6)	0.4289 (6)	0.119 (4)
H23	1.3899	0.2779	0.4504	0.142*
C24	1.1484 (13)	0.3046 (6)	0.4607 (4)	0.096 (3)
H24	1.1501	0.2983	0.5047	0.116*
N1	0.5540 (7)	0.3992 (4)	0.7715 (2)	0.0621 (15)
N2	0.1223 (7)	0.4308 (5)	0.6515 (3)	0.0822 (19)
N3	0.9188 (5)	0.6550 (3)	0.46196 (18)	0.0381 (11)
H3A	0.9071	0.6881	0.4977	0.046*
N4	1.4309 (6)	0.7425 (3)	0.4133 (2)	0.0441 (12)
N5	0.8069 (6)	0.5288 (3)	0.39332 (17)	0.0398 (11)
H5A	0.8458	0.5665	0.3623	0.048*
N6	1.0051 (8)	0.3245 (4)	0.4330 (3)	0.0757 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.036 (3)	0.035 (3)	0.030 (3)	0.000 (3)	0.000 (3)	0.004 (2)
C2	0.032 (3)	0.046 (3)	0.040 (3)	−0.001 (3)	−0.004 (3)	0.006 (3)
C3	0.042 (4)	0.042 (3)	0.035 (3)	0.000 (3)	−0.005 (3)	0.007 (3)
C4	0.034 (3)	0.038 (3)	0.030 (3)	0.000 (3)	0.001 (3)	−0.002 (2)
C5	0.031 (3)	0.044 (3)	0.038 (3)	−0.005 (3)	−0.003 (3)	0.004 (2)
C6	0.045 (4)	0.046 (3)	0.031 (3)	0.000 (3)	−0.008 (3)	0.008 (3)
C7	0.038 (4)	0.047 (3)	0.032 (3)	0.000 (3)	0.000 (3)	0.005 (2)
C8	0.045 (4)	0.050 (3)	0.033 (3)	−0.006 (3)	0.007 (3)	−0.002 (3)
C9	0.049 (4)	0.063 (4)	0.040 (4)	0.006 (3)	0.007 (4)	0.021 (3)
C10	0.034 (3)	0.036 (3)	0.033 (3)	0.007 (3)	0.002 (3)	−0.002 (2)
C11	0.046 (4)	0.041 (3)	0.035 (3)	−0.004 (3)	0.005 (3)	−0.003 (2)
C12	0.047 (4)	0.053 (3)	0.059 (4)	0.003 (3)	0.006 (4)	0.009 (3)
C13	0.034 (3)	0.048 (3)	0.042 (3)	0.005 (3)	0.001 (3)	0.002 (3)
C14	0.050 (5)	0.082 (4)	0.044 (4)	−0.014 (4)	−0.003 (4)	−0.016 (3)
C15	0.073 (6)	0.107 (5)	0.039 (4)	−0.002 (5)	0.010 (4)	−0.019 (4)
C16	0.051 (5)	0.089 (5)	0.055 (4)	−0.008 (4)	0.013 (4)	0.001 (4)
C17	0.051 (4)	0.049 (3)	0.061 (4)	−0.011 (3)	−0.001 (4)	−0.006 (3)
C18	0.052 (4)	0.050 (3)	0.049 (3)	−0.013 (3)	0.000 (4)	−0.010 (3)
C19	0.069 (5)	0.052 (3)	0.048 (4)	−0.005 (3)	0.004 (4)	−0.017 (3)
C20	0.055 (5)	0.041 (3)	0.066 (5)	−0.007 (3)	0.004 (4)	−0.016 (3)
C21	0.070 (6)	0.085 (5)	0.105 (6)	−0.011 (5)	0.012 (6)	−0.052 (5)
C22	0.067 (7)	0.118 (7)	0.193 (12)	−0.008 (6)	0.018 (10)	−0.090 (9)
C23	0.073 (7)	0.063 (5)	0.220 (13)	0.002 (5)	−0.036 (11)	−0.021 (7)
C24	0.099 (7)	0.077 (5)	0.113 (7)	−0.017 (6)	−0.037 (7)	0.028 (5)
N1	0.064 (4)	0.088 (3)	0.034 (3)	−0.009 (3)	−0.004 (3)	0.007 (3)
N2	0.046 (4)	0.129 (5)	0.072 (4)	0.001 (4)	−0.003 (4)	0.046 (4)
N3	0.043 (3)	0.043 (2)	0.029 (2)	−0.006 (2)	0.005 (2)	−0.0062 (19)
N4	0.046 (3)	0.046 (2)	0.041 (3)	−0.003 (3)	0.007 (3)	0.000 (2)
N5	0.052 (3)	0.037 (2)	0.030 (2)	−0.007 (2)	0.002 (3)	−0.0056 (19)
N6	0.079 (5)	0.075 (4)	0.072 (4)	−0.009 (4)	−0.011 (4)	0.016 (3)

Geometric parameters (Å, º)

C1—C6	1.393 (7)	C12—C13	1.502 (7)
C1—C2	1.403 (6)	C13—N4	1.339 (6)
C1—C7	1.445 (7)	C13—C14	1.389 (7)
C2—C3	1.378 (6)	C14—C15	1.369 (8)
C3—C4	1.383 (7)	C15—C16	1.356 (8)
C4—C5	1.395 (6)	C16—C17	1.367 (7)
C4—C10	1.468 (6)	C17—N4	1.328 (7)
C5—C6	1.379 (6)	C18—N5	1.463 (5)
C7—C9	1.379 (9)	C18—C19	1.519 (7)
C7—C8	1.401 (7)	C19—C20	1.495 (8)
C8—N1	1.154 (6)	C20—N6	1.324 (8)
C9—N2	1.154 (8)	C20—C21	1.362 (9)
C10—N5	1.317 (5)	C21—C22	1.378 (12)
C10—N3	1.334 (6)	C22—C23	1.349 (12)
C11—N3	1.464 (6)	C23—C24	1.374 (12)
C11—C12	1.497 (7)	C24—N6	1.336 (10)
C6—C1—C2	116.7 (5)	N4—C13—C14	120.9 (5)
C6—C1—C7	123.0 (5)	N4—C13—C12	116.6 (5)
C2—C1—C7	120.3 (5)	C14—C13—C12	122.5 (5)
C3—C2—C1	121.7 (5)	C15—C14—C13	119.2 (6)
C2—C3—C4	120.5 (5)	C16—C15—C14	119.9 (6)
C3—C4—C5	118.9 (5)	C15—C16—C17	118.0 (6)
C3—C4—C10	120.8 (5)	N4—C17—C16	123.7 (6)
C5—C4—C10	120.2 (5)	N5—C18—C19	110.7 (5)
C6—C5—C4	120.1 (5)	C20—C19—C18	113.1 (5)
C5—C6—C1	122.0 (5)	N6—C20—C21	123.2 (8)
C9—C7—C8	117.4 (6)	N6—C20—C19	116.6 (7)
C9—C7—C1	121.6 (6)	C21—C20—C19	120.1 (7)
C8—C7—C1	120.8 (5)	C20—C21—C22	118.8 (9)
N1—C8—C7	179.1 (6)	C23—C22—C21	119.9 (13)
N2—C9—C7	178.1 (8)	C22—C23—C24	117.1 (13)
N5—C10—N3	120.7 (5)	N6—C24—C23	124.8 (9)
N5—C10—C4	122.4 (5)	C10—N3—C11	126.6 (4)
N3—C10—C4	116.9 (4)	C17—N4—C13	118.3 (5)
N3—C11—C12	110.8 (4)	C10—N5—C18	125.2 (4)
C11—C12—C13	113.9 (4)	C20—N6—C24	116.2 (7)

(AEPrDQ)

Crystal data

C22H30N6	F(000) = 816
Mr = 378.52	Dx = 1.168 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.1430 (12) Å	Cell parameters from 7115 reflections
b = 10.3517 (9) Å	θ = 2.4–25.5°
c = 16.1607 (15) Å	µ = 0.07 mm^−1
β = 101.651 (1)°	T = 293 K
V = 2153.4 (3) Å^3	Plate, pale yellow
Z = 4	0.32 × 0.18 × 0.12 mm

Data collection

CCD area detector diffractometer	4206 independent reflections
Radiation source: sealed tube	2879 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
phi and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan sadabs	h = −16→16
Tmin = 0.972, Tmax = 0.982	k = −12→12
21689 measured reflections	l = −19→19

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.0841P)^2 + 0.2303P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4206 reflections	Δρmax = 0.16 e Å^−3
253 parameters	Δρmin = −0.18 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	1.09780 (12)	0.08555 (15)	0.74299 (10)	0.0517 (4)
C2	1.03813 (13)	0.19874 (15)	0.72666 (10)	0.0565 (4)
H2	1.0515	0.2672	0.7646	0.068*
C3	0.96114 (13)	0.21071 (15)	0.65658 (10)	0.0573 (4)
H3	0.9235	0.2873	0.6477	0.069*
C4	0.93754 (12)	0.11085 (15)	0.59788 (10)	0.0530 (4)
C5	0.99641 (13)	−0.00194 (15)	0.61344 (10)	0.0557 (4)
H5	0.9824	−0.0704	0.5756	0.067*
C6	1.07419 (13)	−0.01392 (15)	0.68318 (11)	0.0553 (4)
H6	1.1125	−0.0900	0.6913	0.066*
C7	1.17782 (13)	0.07278 (15)	0.81767 (11)	0.0581 (4)
C8	1.19386 (15)	0.17185 (18)	0.87777 (12)	0.0692 (5)
C9	1.24025 (14)	−0.03791 (19)	0.83272 (12)	0.0671 (5)
C10	0.84906 (13)	0.12057 (16)	0.52686 (10)	0.0546 (4)
C11	0.89483 (15)	0.33843 (18)	0.48346 (11)	0.0678 (5)
H11A	0.9650	0.3136	0.5100	0.081*
H11B	0.8737	0.4085	0.5161	0.081*
C12	0.89369 (14)	0.38437 (17)	0.39536 (11)	0.0644 (5)
H12A	0.9490	0.4469	0.3969	0.077*
H12B	0.9078	0.3117	0.3615	0.077*
C13	0.77946 (19)	0.5709 (2)	0.38667 (14)	0.0870 (6)
H13A	0.8441	0.6190	0.3994	0.104*
H13B	0.7511	0.5652	0.4375	0.104*
C14	0.7033 (2)	0.6350 (2)	0.31651 (18)	0.1098 (8)
H14A	0.6348	0.6384	0.3302	0.132*
H14B	0.7254	0.7224	0.3074	0.132*
C15	0.7014 (2)	0.5539 (3)	0.23924 (16)	0.1098 (8)
H15A	0.6361	0.5079	0.2236	0.132*
H15B	0.7112	0.6069	0.1920	0.132*
C16	0.78976 (17)	0.4620 (2)	0.26457 (12)	0.0779 (6)
H16A	0.7760	0.3810	0.2342	0.093*
H16B	0.8538	0.4984	0.2537	0.093*
C17	0.70982 (16)	−0.0019 (2)	0.43182 (14)	0.0828 (6)
H17A	0.6996	−0.0938	0.4217	0.099*
H17B	0.7326	0.0348	0.3834	0.099*
C18	0.60789 (16)	0.0581 (3)	0.43856 (16)	0.0967 (7)
H18A	0.5526	0.0160	0.3989	0.116*
H18B	0.5955	0.0438	0.4950	0.116*
C19	0.5722 (2)	0.2275 (3)	0.33234 (17)	0.1097 (9)
H19A	0.5345	0.1560	0.3015	0.132*
H19B	0.6321	0.2467	0.3079	0.132*
C20	0.5037 (3)	0.3432 (4)	0.3279 (3)	0.1646 (16)
H20A	0.5265	0.4105	0.2940	0.198*
H20B	0.4324	0.3209	0.3031	0.198*
C21	0.5123 (3)	0.3862 (4)	0.4145 (4)	0.191 (2)
H21A	0.4483	0.4265	0.4224	0.229*
H21B	0.5689	0.4473	0.4302	0.229*
C22	0.5330 (3)	0.2659 (4)	0.4647 (2)	0.1501 (13)
H22A	0.5652	0.2844	0.5229	0.180*
H22B	0.4695	0.2175	0.4634	0.180*
N1	1.20299 (18)	0.25583 (18)	0.92484 (12)	0.1015 (7)
N2	1.28847 (15)	−0.13103 (19)	0.84314 (13)	0.1010 (6)
N3	0.82533 (11)	0.22851 (13)	0.48398 (9)	0.0591 (4)
H3A	0.7637	0.2347	0.4538	0.071*
N4	0.79633 (11)	0.44279 (13)	0.35509 (9)	0.0600 (4)
N5	0.79115 (11)	0.01659 (14)	0.50634 (10)	0.0663 (4)
H5A	0.8029	−0.0473	0.5410	0.080*
N6	0.60484 (12)	0.19482 (19)	0.42147 (11)	0.0836 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0549 (9)	0.0487 (9)	0.0525 (9)	−0.0040 (7)	0.0134 (7)	0.0028 (7)
C2	0.0696 (10)	0.0481 (9)	0.0517 (9)	0.0023 (8)	0.0119 (8)	−0.0024 (7)
C3	0.0659 (10)	0.0502 (9)	0.0561 (10)	0.0081 (8)	0.0132 (8)	0.0037 (7)
C4	0.0579 (9)	0.0526 (9)	0.0489 (9)	−0.0003 (7)	0.0117 (7)	0.0035 (7)
C5	0.0634 (10)	0.0508 (9)	0.0532 (9)	−0.0012 (7)	0.0127 (8)	−0.0040 (7)
C6	0.0587 (10)	0.0468 (9)	0.0596 (10)	0.0041 (7)	0.0103 (8)	0.0001 (7)
C7	0.0629 (10)	0.0490 (9)	0.0593 (10)	−0.0017 (8)	0.0051 (8)	0.0012 (7)
C8	0.0848 (13)	0.0571 (11)	0.0583 (11)	0.0011 (9)	−0.0031 (9)	0.0063 (9)
C9	0.0624 (11)	0.0603 (11)	0.0718 (12)	−0.0053 (9)	−0.0027 (9)	−0.0004 (9)
C10	0.0558 (9)	0.0543 (10)	0.0545 (9)	−0.0006 (7)	0.0133 (7)	0.0025 (7)
C11	0.0689 (11)	0.0614 (11)	0.0674 (11)	−0.0094 (9)	0.0003 (9)	0.0090 (9)
C12	0.0664 (11)	0.0564 (10)	0.0706 (11)	−0.0041 (8)	0.0147 (9)	0.0055 (8)
C13	0.1006 (16)	0.0693 (13)	0.0899 (15)	0.0094 (11)	0.0162 (12)	−0.0098 (11)
C14	0.115 (2)	0.0844 (16)	0.129 (2)	0.0318 (14)	0.0199 (16)	0.0228 (15)
C15	0.114 (2)	0.128 (2)	0.0856 (17)	0.0247 (17)	0.0154 (14)	0.0364 (16)
C16	0.0930 (14)	0.0794 (13)	0.0614 (11)	0.0021 (11)	0.0160 (10)	0.0084 (10)
C17	0.0795 (14)	0.0676 (12)	0.0904 (15)	−0.0170 (10)	−0.0085 (11)	0.0013 (10)
C18	0.0653 (13)	0.1104 (19)	0.1083 (18)	−0.0213 (12)	0.0031 (12)	0.0266 (14)
C19	0.0949 (17)	0.116 (2)	0.1028 (19)	−0.0192 (15)	−0.0172 (14)	0.0185 (15)
C20	0.138 (3)	0.115 (3)	0.209 (4)	−0.002 (2)	−0.040 (3)	0.042 (3)
C21	0.110 (3)	0.143 (3)	0.288 (6)	0.033 (2)	−0.035 (3)	−0.057 (4)
C22	0.093 (2)	0.201 (4)	0.151 (3)	0.023 (2)	0.0119 (19)	−0.043 (3)
N1	0.1469 (18)	0.0708 (11)	0.0713 (11)	0.0130 (11)	−0.0148 (11)	−0.0117 (9)
N2	0.0875 (13)	0.0760 (12)	0.1235 (16)	0.0184 (10)	−0.0164 (11)	−0.0050 (11)
N3	0.0545 (8)	0.0574 (8)	0.0612 (8)	−0.0044 (6)	0.0015 (6)	0.0088 (6)
N4	0.0691 (9)	0.0523 (8)	0.0573 (8)	−0.0004 (7)	0.0097 (7)	0.0026 (6)
N5	0.0682 (9)	0.0577 (9)	0.0679 (9)	−0.0084 (7)	0.0019 (7)	0.0071 (7)
N6	0.0597 (10)	0.0955 (13)	0.0902 (12)	−0.0012 (9)	0.0021 (9)	−0.0004 (10)

Geometric parameters (Å, º)

C1—C6	1.403 (2)	C14—H14A	0.9700
C1—C2	1.405 (2)	C14—H14B	0.9700
C1—C7	1.438 (2)	C15—C16	1.493 (3)
C2—C3	1.363 (2)	C15—H15A	0.9700
C2—H2	0.9300	C15—H15B	0.9700
C3—C4	1.395 (2)	C16—N4	1.461 (2)
C3—H3	0.9300	C16—H16A	0.9700
C4—C5	1.395 (2)	C16—H16B	0.9700
C4—C10	1.463 (2)	C17—N5	1.452 (2)
C5—C6	1.366 (2)	C17—C18	1.500 (3)
C5—H5	0.9300	C17—H17A	0.9700
C6—H6	0.9300	C17—H17B	0.9700
C7—C8	1.399 (3)	C18—N6	1.441 (3)
C7—C9	1.402 (3)	C18—H18A	0.9700
C8—N1	1.145 (2)	C18—H18B	0.9700
C9—N2	1.147 (2)	C19—N6	1.457 (3)
C10—N3	1.319 (2)	C19—C20	1.490 (4)
C10—N5	1.321 (2)	C19—H19A	0.9700
C11—N3	1.460 (2)	C19—H19B	0.9700
C11—C12	1.498 (2)	C20—C21	1.452 (6)
C11—H11A	0.9700	C20—H20A	0.9700
C11—H11B	0.9700	C20—H20B	0.9700
C12—N4	1.446 (2)	C21—C22	1.481 (6)
C12—H12A	0.9700	C21—H21A	0.9700
C12—H12B	0.9700	C21—H21B	0.9700
C13—N4	1.454 (2)	C22—N6	1.480 (4)
C13—C14	1.507 (3)	C22—H22A	0.9700
C13—H13A	0.9700	C22—H22B	0.9700
C13—H13B	0.9700	N3—H3A	0.8600
C14—C15	1.501 (4)	N5—H5A	0.8600
C6—C1—C2	116.43 (14)	H15A—C15—H15B	108.9
C6—C1—C7	122.22 (14)	N4—C16—C15	104.27 (18)
C2—C1—C7	121.35 (14)	N4—C16—H16A	110.9
C3—C2—C1	121.62 (15)	C15—C16—H16A	110.9
C3—C2—H2	119.2	N4—C16—H16B	110.9
C1—C2—H2	119.2	C15—C16—H16B	110.9
C2—C3—C4	121.56 (15)	H16A—C16—H16B	108.9
C2—C3—H3	119.2	N5—C17—C18	113.8 (2)
C4—C3—H3	119.2	N5—C17—H17A	108.8
C3—C4—C5	117.29 (14)	C18—C17—H17A	108.8
C3—C4—C10	120.99 (14)	N5—C17—H17B	108.8
C5—C4—C10	121.53 (14)	C18—C17—H17B	108.8
C6—C5—C4	121.34 (15)	H17A—C17—H17B	107.7
C6—C5—H5	119.3	N6—C18—C17	112.53 (17)
C4—C5—H5	119.3	N6—C18—H18A	109.1
C5—C6—C1	121.75 (15)	C17—C18—H18A	109.1
C5—C6—H6	119.1	N6—C18—H18B	109.1
C1—C6—H6	119.1	C17—C18—H18B	109.1
C8—C7—C9	118.56 (15)	H18A—C18—H18B	107.8
C8—C7—C1	119.83 (15)	N6—C19—C20	106.8 (3)
C9—C7—C1	121.61 (15)	N6—C19—H19A	110.4
N1—C8—C7	176.8 (2)	C20—C19—H19A	110.4
N2—C9—C7	177.5 (2)	N6—C19—H19B	110.4
N3—C10—N5	119.69 (15)	C20—C19—H19B	110.4
N3—C10—C4	122.46 (14)	H19A—C19—H19B	108.6
N5—C10—C4	117.85 (14)	C21—C20—C19	105.7 (3)
N3—C11—C12	111.50 (14)	C21—C20—H20A	110.6
N3—C11—H11A	109.3	C19—C20—H20A	110.6
C12—C11—H11A	109.3	C21—C20—H20B	110.6
N3—C11—H11B	109.3	C19—C20—H20B	110.6
C12—C11—H11B	109.3	H20A—C20—H20B	108.7
H11A—C11—H11B	108.0	C20—C21—C22	103.9 (3)
N4—C12—C11	113.49 (15)	C20—C21—H21A	111.0
N4—C12—H12A	108.9	C22—C21—H21A	111.0
C11—C12—H12A	108.9	C20—C21—H21B	111.0
N4—C12—H12B	108.9	C22—C21—H21B	111.0
C11—C12—H12B	108.9	H21A—C21—H21B	109.0
H12A—C12—H12B	107.7	N6—C22—C21	102.9 (3)
N4—C13—C14	105.23 (18)	N6—C22—H22A	111.2
N4—C13—H13A	110.7	C21—C22—H22A	111.2
C14—C13—H13A	110.7	N6—C22—H22B	111.2
N4—C13—H13B	110.7	C21—C22—H22B	111.2
C14—C13—H13B	110.7	H22A—C22—H22B	109.1
H13A—C13—H13B	108.8	C10—N3—C11	125.55 (14)
C15—C14—C13	106.06 (19)	C10—N3—H3A	117.2
C15—C14—H14A	110.5	C11—N3—H3A	117.2
C13—C14—H14A	110.5	C12—N4—C13	114.05 (15)
C15—C14—H14B	110.5	C12—N4—C16	112.04 (15)
C13—C14—H14B	110.5	C13—N4—C16	104.19 (15)
H14A—C14—H14B	108.7	C10—N5—C17	127.26 (16)
C16—C15—C14	104.3 (2)	C10—N5—H5A	116.4
C16—C15—H15A	110.9	C17—N5—H5A	116.4
C14—C15—H15A	110.9	C18—N6—C19	114.1 (2)
C16—C15—H15B	110.9	C18—N6—C22	113.2 (2)
C14—C15—H15B	110.9	C19—N6—C22	105.2 (2)