Crystal structure of trans-(1,8-dibutyl-1,3,6,8,10,13-hexa-aza-cyclo-tetra-decane-κ(4) N (3),N (6),N (10),N (13))bis-(isonicotinato-κO)nickel(II) determined from synchrotron data.

The title compound, [Ni(C6H4NO2)2(C16H38N6)], was prepared through self-assembly of a nickel(II) aza-macrocyclic complex with isonicotinic acid. The Ni(II) atom is located on an inversion center and exhibits a distorted octa-hedral N4O2 coordination environment, with the four secondary N atoms of the aza-macrocyclic ligand in the equatorial plane [average Ni-Neq = 2.064 (11) Å] and two O atoms of monodentate isonicotinate anions in axial positions [Ni-Oax = 2.137 (1) Å]. Intra-molecular N-H⋯O hydrogen bonds between one of the secondary amine N atoms of the aza-macrocyclic ligand and the non-coordinating carboxyl-ate O atom of the anion stabilize the mol-ecular structure. Inter-molecular N-H⋯N hydrogen bonds, as well as π-π inter-actions between neighbouring pyridine rings, give rise to the formations of supra-molecular ribbons extending parallel to [001].

Chemical context

The mol­ecular design and synthesis of coordination polymers with macrocyclic ligands have attracted considerable attention because of their potential applications in chemistry, environmental chemistry, and materials science (Churchard et al., 2010 ▸; Lehn, 2015 ▸). To obtain specific mol­ecular compounds through assembly of supra­molecular building blocks with properties such as guest recognition or catalytic effects, macrocyclic complexes involving vacant sites in an axial position are good candidates. Moreover, these complexes can also be easily derivatized by carb­oxy­lic acid moieties, such as 1,3,5-BTC (1,3,5-benzene­tri­carb­oxy­lic acid), 2,7-NDC (2,7-naphthalenedi­carb­oxy­lic acid) or 1,3,5-CTC (1,3,5-cyclo­hexa­netri­carb­oxy­lic acid), forming inter­esting coordination compounds with supra­molecular structures ranging from chains to networks (Min & Suh, 2001 ▸; Shin et al., 2016b ▸). For example, [Ni(L,)]3[BTC3–]2·12H2O·CH3CN (L, = 1,8-bis­[(R)-α-methyl­benz­yl]-1,3,6,8,10,13-hexa­aza­cyclo­tetra­deca­ne) displays a two-dimensional supra­molecular network structure and exhibits a selective chiral recognition for racemic material (Ryoo et al., 2010 ▸). Isonicotinic acid as another building unit can easily bind or inter­act with transition metal ions through its possible bridging or coordination modes associated with the carb­oxy­lic group and pyridine moieties, respectively, thus allowing the assembly of compounds with supra­molecular structures or the formation of heterometallic complexes (Xie et al., 2014 ▸).

Here, we report on the synthesis and crystal structure of an NiII aza­macrocyclic complex including isonicotinate anions, [Ni(C6H4NO2)2(C16H38N6)], (I).

Structural commentary

Compound (I) is isotypic with its copper(II) analogue (Shin et al., 2015 ▸). The nickel(II) atom is located on an inversion center. The coordination environment around the nickel(II) atom is distorted octa­hedral with the four secondary amine N atoms of the aza­macrocyclic ligand in the equatorial plane and two O atoms of two monodentate isonicotinate anions in axial positions (Fig. 1 ▸). The average Ni—Neq bond lengths is 2.064 (11) Å and the Ni—Oax bond length is 2.137 (1) Å. The longer axial bonds can be attributed to a ring contraction of the aza­macrocyclic ligand (Melson, 1979 ▸). The six-membered NiC2N3 ring (Ni1–N1–C2–N3–C3–N2) adopts the expected chair conformation, whereas the five-membered NiC2N2 ring (Ni1–N1–C1–C4–N2) has a gauche conformation (Min & Suh, 2001 ▸). Since the carboxyl­ate group is fully delocalized, the two C—O bonds and the bond angle (O1—C9—O2) are 1.267 (2), 1.248 (2) Å and 126.9 (2)°, respectively. The bond angles around the nickel(II) atom are in the normal range for an octa­hedral complex. Intra­molecular N—H⋯O hydrogen bonds between one of the secondary amine groups of the aza­macrocyclic ligand and the non-coordinating carboxyl­ate O atom of the isonicotinate anion form six-membered rings and stabilize the mol­ecular structure (Fig. 1 ▸, Table 1 ▸).

Figure 1

View of the mol­ecular structure of the title compound, showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level. H atoms bonded to C atoms have been omitted for clarity. Intra­molecular N—H⋯O hydrogen bonds are shown as red dashed lines. [Symmetry code: (i) −x + 1, −y + 1, −z + 1.]

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	1.00	1.98	2.892 (2)	150
N2—H2⋯N4i	1.00	2.23	3.143 (2)	151

Symmetry code: (i) .

Supra­molecular features

The N4 atom of the isonicotinate anion forms an inter­molecular hydrogen bond with an adjacent secondary amine group of the aza­macrocyclic ligand (Fig. 2 ▸, Table 1 ▸) (Steed & Atwood, 2009 ▸). In addition, parallel pyridine rings (Hunter & Sanders, 1990 ▸) of the isonicotinate anions participate in π–π inter­actions with a centroid-to-centroid distance of 3.741 (1) Å and an inter­planar separation of 3.547 (1) Å. The inter­play between hydrogen bonds and π–π inter­actions give rise to the formation of supra­molecular ribbons extending parallel to [001].

Figure 2

View of the crystal packing of the title compound, showing hydrogen bonds and π–π inter­actions (red: intra­molecular N—H⋯O hydrogen bonds, green: inter­molecular N—H⋯N hydrogen bonds, black: π–π inter­actions).

Database survey

A search of the Cambridge Structural Database (Version 5.36, May 2014 with 3 updates; Groom & Allen, 2014 ▸) reveals two complexes with the same nickel(II) aza­macrocyclic building block (Kim et al., 2015 ▸) for which synthesis, FT–IR spectroscopic data and the crystal structure have been reported.

Synthesis and crystallization

The starting complex, [Ni(C16H38N6)(ClO4)2], was prepared in a slightly modified procedure with respect to the reported method (Kim et al., 2015b ▸). To an aceto­nitrile solution (14 mL) of [Ni(C16H38N6)(ClO4)2] (0.298 g, 0.52 mmol) was slowly added an aceto­nitrile solution (8 mL) containing isonicotinic acid (0.128 g, 1.04 mmol) and excess tri­ethyl­amine (0.12 g, 1.20 mmol) at room temperature. The purple precipitate was filtered off, washed with aceto­nitrile and diethyl ether, and dried in air. Single crystals of compound (l) were obtained by layering of the aceto­nitrile solution of isonicotinic acid on the aceto­nitrile solution of [Ni(C16H38N6)(ClO4)2] for several days. Yield: 0.167 g (52%). FT–IR (ATR, cm−1): 3145, 3075, 2951, 2920, 1571, 1457, 1351, 1272, 1014, 915.

Safety note: Although we have experienced no problems with the compounds reported in this study, perchlorate salts of metal complexes are often explosive and should be handled with great caution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.95 (ring H atoms) or 0.98–0.99 Å (open-chain H atoms), and an N—H distance of 1.0 Å, with U iso(H) values of 1.2 or 1.5U eq of the parent atoms.

Table 2

Experimental details

Crystal data
Chemical formula	[Ni(C6H4NO2)2(C16H38N6)]
M r	617.44
Crystal system, space group	Triclinic, P
Temperature (K)	100
a, b, c (Å)	8.0630 (16), 8.5110 (17), 10.927 (2)
α, β, γ (°)	80.52 (3), 88.26 (3), 86.44 (3)
V (Å3)	738.0 (3)
Z	1
Radiation type	Synchrotron, λ = 0.62998 Å
μ (mm−1)	0.51
Crystal size (mm)	0.01 × 0.004 × 0.004
Data collection
Diffractometer	ADSC Q210 CCD area detector
Absorption correction	Empirical (HKL-3000SM SCALEPACK; Otwinowski & Minor, 1997 ▸)
T min, T max	0.995, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	7634, 3879, 3326
R int	0.023
(sin θ/λ)max (Å−1)	0.696
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.040, 0.110, 1.04
No. of reflections	3879
No. of parameters	188
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	1.12, −0.95

Computer programs: PAL BL2D-SMDC (Shin et al., 2016 ▸ a), HKL-3000SM (Otwinowski & Minor, 1997 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL2014 (Sheldrick, 2015b ▸), DIAMOND (Putz & Brandenburg, 2014 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989016001031/wm5263sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016001031/wm5263Isup2.hkl

CCDC reference: 1447865

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Ni(C6H4NO2)2(C16H38N6)]	Z = 1
Mr = 617.44	F(000) = 330
Triclinic, P1	Dx = 1.389 Mg m−3
a = 8.0630 (16) Å	Synchrotron radiation, λ = 0.62998 Å
b = 8.5110 (17) Å	Cell parameters from 20128 reflections
c = 10.927 (2) Å	θ = 0.4–33.6°
α = 80.52 (3)°	µ = 0.51 mm−1
β = 88.26 (3)°	T = 100 K
γ = 86.44 (3)°	Needle, pale pink
V = 738.0 (3) Å3	0.01 × 0.004 × 0.004 mm

ADSC Q210 CCD area-detector diffractometer	3326 reflections with I > 2σ(I)
Radiation source: PLSII 2D bending magnet	Rint = 0.023
ω scan	θmax = 26.0°, θmin = 2.5°
Absorption correction: empirical (using intensity measurements) (HKL-3000SM SCALEPACK; Otwinowski & Minor, 1997)	h = −11→11
Tmin = 0.995, Tmax = 0.998	k = −11→11
7634 measured reflections	l = −15→15
3879 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0649P)2 + 0.1918P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3879 reflections	Δρmax = 1.12 e Å−3
188 parameters	Δρmin = −0.95 e Å−3

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

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.5000	0.5000	0.02066 (10)
O1	0.43513 (15)	0.41029 (17)	0.33736 (11)	0.0257 (3)
O2	0.18613 (16)	0.52908 (19)	0.28022 (12)	0.0322 (3)
N1	0.27809 (18)	0.6311 (2)	0.50735 (13)	0.0244 (3)
H1	0.2171	0.6276	0.4296	0.029*
N2	0.61452 (18)	0.67953 (19)	0.38249 (13)	0.0241 (3)
H2	0.5798	0.6766	0.2959	0.029*
N3	0.3946 (2)	0.8835 (2)	0.41256 (14)	0.0304 (3)
N4	0.3686 (2)	0.2837 (2)	−0.09149 (14)	0.0335 (4)
C1	0.1835 (2)	0.5457 (3)	0.61221 (15)	0.0276 (4)
H1A	0.0642	0.5807	0.6057	0.033*
H1B	0.2242	0.5692	0.6915	0.033*
C2	0.3004 (2)	0.8006 (2)	0.51521 (16)	0.0296 (4)
H2A	0.1895	0.8566	0.5192	0.036*
H2B	0.3574	0.8058	0.5933	0.036*
C3	0.5703 (2)	0.8414 (2)	0.41070 (18)	0.0308 (4)
H3A	0.6153	0.8493	0.4926	0.037*
H3B	0.6249	0.9202	0.3480	0.037*
C4	0.7938 (2)	0.6330 (3)	0.39084 (16)	0.0280 (4)
H4A	0.8376	0.6572	0.4689	0.034*
H4B	0.8552	0.6932	0.3203	0.034*
C5	0.3160 (2)	0.9034 (2)	0.29077 (17)	0.0310 (4)
H5A	0.2983	0.7968	0.2700	0.037*
H5B	0.3922	0.9575	0.2269	0.037*
C6	0.1502 (3)	0.9999 (3)	0.28701 (18)	0.0341 (4)
H6A	0.0727	0.9447	0.3493	0.041*
H6B	0.1671	1.1058	0.3093	0.041*
C7	0.0730 (3)	1.0223 (3)	0.15954 (19)	0.0390 (5)
H7A	0.1527	1.0726	0.0966	0.047*
H7B	0.0507	0.9166	0.1390	0.047*
C8	−0.0882 (3)	1.1257 (4)	0.1543 (2)	0.0502 (6)
H8A	−0.1692	1.0739	0.2140	0.075*
H8B	−0.1328	1.1395	0.0705	0.075*
H8C	−0.0667	1.2302	0.1750	0.075*
C9	0.3163 (2)	0.4477 (2)	0.26295 (15)	0.0235 (3)
C10	0.4760 (2)	0.2978 (3)	0.10910 (16)	0.0294 (4)
H10	0.5631	0.2691	0.1666	0.035*
C11	0.3367 (2)	0.3884 (2)	0.13963 (14)	0.0234 (3)
C12	0.2134 (2)	0.4252 (3)	0.05120 (16)	0.0300 (4)
H12	0.1158	0.4874	0.0676	0.036*
C13	0.2347 (2)	0.3703 (3)	−0.06044 (17)	0.0339 (4)
H13	0.1486	0.3957	−0.1191	0.041*
C14	0.4868 (2)	0.2496 (3)	−0.00601 (17)	0.0340 (4)
H14	0.5838	0.1887	−0.0256	0.041*

	U11	U22	U33	U12	U13	U23
Ni1	0.01767 (15)	0.03464 (19)	0.00987 (14)	0.00142 (11)	−0.00201 (9)	−0.00504 (11)
O1	0.0246 (6)	0.0412 (7)	0.0122 (5)	0.0012 (5)	−0.0054 (4)	−0.0073 (5)
O2	0.0235 (6)	0.0543 (9)	0.0207 (6)	0.0047 (6)	−0.0043 (5)	−0.0139 (6)
N1	0.0225 (7)	0.0384 (8)	0.0122 (6)	0.0027 (6)	−0.0022 (5)	−0.0048 (6)
N2	0.0227 (7)	0.0355 (8)	0.0142 (6)	0.0007 (6)	−0.0016 (5)	−0.0049 (6)
N3	0.0338 (8)	0.0354 (9)	0.0209 (7)	0.0055 (7)	−0.0018 (6)	−0.0041 (7)
N4	0.0344 (8)	0.0525 (11)	0.0148 (6)	0.0002 (7)	−0.0027 (6)	−0.0091 (7)
C1	0.0186 (7)	0.0485 (11)	0.0149 (7)	0.0026 (7)	0.0012 (5)	−0.0052 (7)
C2	0.0331 (9)	0.0384 (10)	0.0169 (8)	0.0078 (8)	−0.0008 (6)	−0.0068 (7)
C3	0.0339 (9)	0.0350 (10)	0.0240 (8)	−0.0011 (7)	−0.0018 (7)	−0.0063 (8)
C4	0.0205 (8)	0.0460 (11)	0.0173 (7)	−0.0038 (7)	0.0002 (6)	−0.0043 (7)
C5	0.0376 (10)	0.0345 (10)	0.0188 (8)	0.0059 (8)	−0.0014 (7)	−0.0011 (7)
C6	0.0356 (10)	0.0414 (11)	0.0227 (9)	0.0064 (8)	−0.0008 (7)	−0.0009 (8)
C7	0.0394 (11)	0.0506 (13)	0.0243 (9)	0.0048 (9)	−0.0033 (7)	−0.0006 (9)
C8	0.0400 (12)	0.0733 (18)	0.0320 (11)	0.0119 (11)	−0.0033 (9)	0.0018 (11)
C9	0.0213 (7)	0.0366 (9)	0.0128 (7)	−0.0044 (6)	−0.0018 (5)	−0.0040 (6)
C10	0.0258 (8)	0.0468 (11)	0.0160 (7)	0.0028 (7)	−0.0044 (6)	−0.0071 (7)
C11	0.0222 (7)	0.0365 (9)	0.0119 (7)	−0.0038 (7)	−0.0016 (5)	−0.0047 (7)
C12	0.0257 (8)	0.0484 (11)	0.0158 (7)	0.0020 (8)	−0.0044 (6)	−0.0062 (8)
C13	0.0307 (9)	0.0562 (13)	0.0157 (8)	0.0009 (8)	−0.0073 (6)	−0.0085 (8)
C14	0.0306 (9)	0.0534 (12)	0.0186 (8)	0.0056 (8)	−0.0017 (7)	−0.0106 (8)

Ni1—N1i	2.0559 (16)	C3—H3B	0.9900
Ni1—N1	2.0559 (16)	C4—C1i	1.526 (3)
Ni1—N2	2.0720 (17)	C4—H4A	0.9900
Ni1—N2i	2.0720 (17)	C4—H4B	0.9900
Ni1—O1i	2.1371 (13)	C5—C6	1.523 (3)
Ni1—O1	2.1372 (13)	C5—H5A	0.9900
O1—C9	1.2669 (19)	C5—H5B	0.9900
O2—C9	1.248 (2)	C6—C7	1.521 (3)
N1—C1	1.471 (2)	C6—H6A	0.9900
N1—C2	1.481 (3)	C6—H6B	0.9900
N1—H1	1.0000	C7—C8	1.521 (3)
N2—C4	1.477 (2)	C7—H7A	0.9900
N2—C3	1.481 (3)	C7—H7B	0.9900
N2—H2	1.0000	C8—H8A	0.9800
N3—C3	1.440 (3)	C8—H8B	0.9800
N3—C2	1.444 (2)	C8—H8C	0.9800
N3—C5	1.471 (2)	C9—C11	1.516 (2)
N4—C13	1.336 (3)	C10—C14	1.384 (3)
N4—C14	1.340 (2)	C10—C11	1.386 (3)
C1—C4i	1.526 (3)	C10—H10	0.9500
C1—H1A	0.9900	C11—C12	1.393 (2)
C1—H1B	0.9900	C12—C13	1.379 (3)
C2—H2A	0.9900	C12—H12	0.9500
C2—H2B	0.9900	C13—H13	0.9500
C3—H3A	0.9900	C14—H14	0.9500
N1i—Ni1—N1	180.0	H3A—C3—H3B	107.6
N1i—Ni1—N2	85.97 (6)	N2—C4—C1i	108.14 (15)
N1—Ni1—N2	94.03 (6)	N2—C4—H4A	110.1
N1i—Ni1—N2i	94.03 (6)	C1i—C4—H4A	110.1
N1—Ni1—N2i	85.97 (6)	N2—C4—H4B	110.1
N2—Ni1—N2i	180.0	C1i—C4—H4B	110.1
N1i—Ni1—O1i	93.29 (6)	H4A—C4—H4B	108.4
N1—Ni1—O1i	86.71 (6)	N3—C5—C6	112.79 (16)
N2—Ni1—O1i	92.90 (6)	N3—C5—H5A	109.0
N2i—Ni1—O1i	87.10 (6)	C6—C5—H5A	109.0
N1i—Ni1—O1	86.71 (6)	N3—C5—H5B	109.0
N1—Ni1—O1	93.29 (6)	C6—C5—H5B	109.0
N2—Ni1—O1	87.10 (6)	H5A—C5—H5B	107.8
N2i—Ni1—O1	92.90 (6)	C7—C6—C5	111.93 (17)
O1i—Ni1—O1	180.0	C7—C6—H6A	109.2
C9—O1—Ni1	131.99 (12)	C5—C6—H6A	109.2
C1—N1—C2	114.34 (14)	C7—C6—H6B	109.2
C1—N1—Ni1	105.52 (11)	C5—C6—H6B	109.2
C2—N1—Ni1	112.75 (11)	H6A—C6—H6B	107.9
C1—N1—H1	108.0	C8—C7—C6	111.81 (19)
C2—N1—H1	108.0	C8—C7—H7A	109.3
Ni1—N1—H1	108.0	C6—C7—H7A	109.3
C4—N2—C3	113.96 (15)	C8—C7—H7B	109.3
C4—N2—Ni1	104.76 (11)	C6—C7—H7B	109.3
C3—N2—Ni1	113.72 (11)	H7A—C7—H7B	107.9
C4—N2—H2	108.0	C7—C8—H8A	109.5
C3—N2—H2	108.0	C7—C8—H8B	109.5
Ni1—N2—H2	108.0	H8A—C8—H8B	109.5
C3—N3—C2	115.84 (15)	C7—C8—H8C	109.5
C3—N3—C5	114.58 (15)	H8A—C8—H8C	109.5
C2—N3—C5	115.55 (16)	H8B—C8—H8C	109.5
C13—N4—C14	116.05 (17)	O2—C9—O1	126.88 (16)
N1—C1—C4i	108.60 (14)	O2—C9—C11	117.12 (15)
N1—C1—H1A	110.0	O1—C9—C11	115.99 (16)
C4i—C1—H1A	110.0	C14—C10—C11	119.30 (17)
N1—C1—H1B	110.0	C14—C10—H10	120.4
C4i—C1—H1B	110.0	C11—C10—H10	120.4
H1A—C1—H1B	108.4	C10—C11—C12	117.25 (16)
N3—C2—N1	114.07 (15)	C10—C11—C9	122.61 (15)
N3—C2—H2A	108.7	C12—C11—C9	120.14 (16)
N1—C2—H2A	108.7	C13—C12—C11	119.15 (18)
N3—C2—H2B	108.7	C13—C12—H12	120.4
N1—C2—H2B	108.7	C11—C12—H12	120.4
H2A—C2—H2B	107.6	N4—C13—C12	124.30 (17)
N3—C3—N2	114.51 (16)	N4—C13—H13	117.8
N3—C3—H3A	108.6	C12—C13—H13	117.8
N2—C3—H3A	108.6	N4—C14—C10	123.94 (18)
N3—C3—H3B	108.6	N4—C14—H14	118.0
N2—C3—H3B	108.6	C10—C14—H14	118.0
C2—N1—C1—C4i	−166.23 (14)	C5—C6—C7—C8	−177.2 (2)
Ni1—N1—C1—C4i	−41.74 (15)	Ni1—O1—C9—O2	−15.1 (3)
C3—N3—C2—N1	−72.6 (2)	Ni1—O1—C9—C11	164.15 (12)
C5—N3—C2—N1	65.5 (2)	C14—C10—C11—C12	0.4 (3)
C1—N1—C2—N3	179.49 (14)	C14—C10—C11—C9	−179.18 (18)
Ni1—N1—C2—N3	58.94 (17)	O2—C9—C11—C10	179.64 (18)
C2—N3—C3—N2	70.3 (2)	O1—C9—C11—C10	0.3 (3)
C5—N3—C3—N2	−68.2 (2)	O2—C9—C11—C12	0.1 (3)
C4—N2—C3—N3	−175.30 (14)	O1—C9—C11—C12	−179.24 (17)
Ni1—N2—C3—N3	−55.32 (18)	C10—C11—C12—C13	0.3 (3)
C3—N2—C4—C1i	167.84 (13)	C9—C11—C12—C13	179.86 (18)
Ni1—N2—C4—C1i	42.93 (14)	C14—N4—C13—C12	0.4 (3)
C3—N3—C5—C6	−160.49 (18)	C11—C12—C13—N4	−0.7 (3)
C2—N3—C5—C6	60.9 (2)	C13—N4—C14—C10	0.4 (3)
N3—C5—C6—C7	178.71 (18)	C11—C10—C14—N4	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	1.00	1.98	2.892 (2)	150
N2—H2···N4ii	1.00	2.23	3.143 (2)	151