Ethyl {6-[6-(ethoxy-carbon-yl)picolin-amido-carbon-yl]picolinamido-carbon-yl}picolinate.

The title mol-ecule, C(25)H(21)N(5)O(8), adopts a helical conformation, which is stabilized by two intra-molecular bifurcated N-H⋯(N,N) hydrogen bonds.

Related literature

For a review on aromatic oligoamides (AOAs), see, for example: Huc (2004 ▶). For related compounds, see: Li et al. (2008 ▶).

Experimental

Crystal data

C25H21N5O8

M = 519.47

Monoclinic,

a = 7.4952 (8) Å

b = 19.998 (2) Å

c = 15.9966 (17) Å

β = 96.376 (1)°

V = 2382.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 113 (2) K

0.32 × 0.22 × 0.18 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalcClear; Rigaku, 1999 ▶) T min = 0.966, T max = 0.980

30537 measured reflections

6101 independent reflections

5457 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.096

S = 1.08

6101 reflections

354 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040932/hb2864sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040932/hb2864Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H21N5O8	F(000) = 1080
Mr = 519.47	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 6439 reflections
a = 7.4952 (8) Å	θ = 2.6–26.0°
b = 19.998 (2) Å	µ = 0.11 mm−1
c = 15.9966 (17) Å	T = 113 K
β = 96.376 (1)°	Prism, colorless
V = 2382.8 (4) Å3	0.32 × 0.22 × 0.18 mm
Z = 4

Rigaku Saturn diffractometer	6101 independent reflections
Radiation source: rotating anode	5457 reflections with I > 2σ(I)
confocal	Rint = 0.025
Detector resolution: 7.31 pixels mm-1	θmax = 28.7°, θmin = 2.4°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalcClear; Rigaku, 1999)	k = −27→24
Tmin = 0.966, Tmax = 0.980	l = −21→21
30537 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.4996P] where P = (Fo2 + 2Fc2)/3
6101 reflections	(Δ/σ)max = 0.001
354 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.17 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	−0.13320 (11)	0.87694 (4)	0.72665 (5)	0.02977 (17)
O2	0.06124 (11)	0.85871 (4)	0.63149 (5)	0.02910 (17)
O3	−0.16781 (12)	0.59423 (4)	0.88294 (6)	0.0395 (2)
O4	−0.33384 (11)	0.65393 (4)	1.02334 (5)	0.03521 (19)
O5	−0.24510 (13)	0.99672 (4)	0.94666 (5)	0.0397 (2)
O6	0.08420 (13)	1.00415 (4)	0.86648 (5)	0.0391 (2)
O7	0.21781 (10)	0.70449 (4)	0.93765 (4)	0.02615 (16)
O8	0.37042 (9)	0.67410 (4)	0.82982 (4)	0.02587 (16)
N1	−0.10247 (10)	0.74283 (4)	0.76977 (5)	0.02135 (16)
N2	−0.21026 (12)	0.70511 (4)	0.91366 (5)	0.02446 (18)
N3	−0.25843 (11)	0.82284 (4)	0.97648 (5)	0.02253 (17)
N4	−0.04508 (12)	0.91296 (4)	0.92339 (5)	0.02641 (18)
N5	0.20551 (11)	0.83332 (4)	0.87730 (5)	0.02099 (16)
C1	−0.04508 (13)	0.83975 (5)	0.68831 (6)	0.02336 (19)
C2	−0.03851 (12)	0.76501 (5)	0.70001 (6)	0.02167 (19)
C3	0.02896 (13)	0.72245 (5)	0.64172 (6)	0.0245 (2)
H3	0.0764	0.7400	0.5936	0.029*
C4	0.02507 (13)	0.65399 (5)	0.65576 (6)	0.0264 (2)
H4A	0.0657	0.6237	0.6162	0.032*
C5	−0.03894 (13)	0.63047 (5)	0.72829 (7)	0.0262 (2)
H5	−0.0419	0.5839	0.7398	0.031*
C6	−0.09874 (12)	0.67674 (5)	0.78370 (6)	0.02280 (19)
C7	−0.16141 (13)	0.65290 (5)	0.86502 (7)	0.0260 (2)
C8	−0.29462 (13)	0.70359 (5)	0.98611 (6)	0.0248 (2)
C9	−0.34013 (13)	0.77315 (5)	1.01301 (6)	0.0241 (2)
C10	−0.46393 (14)	0.78407 (7)	1.07012 (7)	0.0334 (2)
H10	−0.5180	0.7478	1.0961	0.040*
C11	−0.50571 (15)	0.84953 (7)	1.08782 (8)	0.0400 (3)
H11	−0.5904	0.8588	1.1263	0.048*
C12	−0.42408 (15)	0.90164 (6)	1.04950 (7)	0.0353 (3)
H12	−0.4530	0.9468	1.0603	0.042*
C13	−0.29831 (14)	0.88586 (5)	0.99470 (6)	0.0263 (2)
C14	−0.19693 (15)	0.93888 (5)	0.95273 (6)	0.0287 (2)
C15	0.08115 (15)	0.94475 (5)	0.88163 (6)	0.0272 (2)
C16	0.22015 (13)	0.89727 (5)	0.85479 (6)	0.0240 (2)
C17	0.35075 (15)	0.92050 (6)	0.80694 (7)	0.0318 (2)
H17	0.3587	0.9667	0.7939	0.038*
C18	0.46885 (15)	0.87489 (6)	0.77877 (8)	0.0350 (3)
H18	0.5603	0.8892	0.7462	0.042*
C19	0.45178 (14)	0.80778 (6)	0.79891 (7)	0.0290 (2)
H19	0.5286	0.7751	0.7788	0.035*
C20	0.31961 (12)	0.78940 (5)	0.84913 (6)	0.02153 (19)
C21	0.29545 (12)	0.71868 (5)	0.87815 (6)	0.02146 (19)
C22	0.06263 (18)	0.92999 (5)	0.61175 (7)	0.0342 (2)
H22A	0.0827	0.9568	0.6640	0.041*
H22B	−0.0532	0.9435	0.5806	0.041*
C23	0.2126 (2)	0.94046 (6)	0.55884 (9)	0.0482 (4)
H23A	0.3267	0.9282	0.5912	0.072*
H23B	0.2163	0.9876	0.5423	0.072*
H23C	0.1931	0.9124	0.5084	0.072*
C24	0.35652 (15)	0.60428 (5)	0.85650 (7)	0.0275 (2)
H24A	0.2315	0.5941	0.8666	0.033*
H24B	0.4356	0.5965	0.9094	0.033*
C25	0.41238 (17)	0.56010 (6)	0.78771 (7)	0.0352 (2)
H25A	0.3290	0.5662	0.7366	0.053*
H25B	0.4104	0.5133	0.8056	0.053*
H25C	0.5341	0.5721	0.7762	0.053*
H4	−0.0313 (18)	0.8692 (7)	0.9284 (8)	0.036 (4)*
H2	−0.1908 (19)	0.7449 (8)	0.8932 (9)	0.040 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0356 (4)	0.0277 (4)	0.0269 (4)	0.0077 (3)	0.0077 (3)	−0.0011 (3)
O2	0.0378 (4)	0.0242 (4)	0.0268 (4)	0.0026 (3)	0.0104 (3)	0.0007 (3)
O3	0.0507 (5)	0.0201 (4)	0.0503 (5)	−0.0036 (3)	0.0176 (4)	0.0003 (3)
O4	0.0350 (4)	0.0360 (4)	0.0355 (4)	−0.0062 (3)	0.0075 (3)	0.0099 (3)
O5	0.0549 (5)	0.0247 (4)	0.0386 (5)	0.0185 (4)	0.0005 (4)	−0.0020 (3)
O6	0.0650 (6)	0.0165 (4)	0.0358 (4)	−0.0003 (4)	0.0059 (4)	0.0058 (3)
O7	0.0308 (4)	0.0222 (4)	0.0266 (4)	0.0031 (3)	0.0085 (3)	0.0035 (3)
O8	0.0267 (4)	0.0239 (4)	0.0280 (4)	0.0045 (3)	0.0076 (3)	0.0009 (3)
N1	0.0193 (4)	0.0215 (4)	0.0231 (4)	−0.0004 (3)	0.0013 (3)	−0.0035 (3)
N2	0.0272 (4)	0.0203 (4)	0.0269 (4)	−0.0018 (3)	0.0075 (3)	0.0004 (3)
N3	0.0231 (4)	0.0256 (4)	0.0186 (4)	0.0055 (3)	0.0007 (3)	−0.0008 (3)
N4	0.0374 (5)	0.0147 (4)	0.0277 (4)	0.0050 (3)	0.0059 (3)	0.0009 (3)
N5	0.0218 (4)	0.0188 (4)	0.0218 (4)	−0.0021 (3)	−0.0004 (3)	0.0022 (3)
C1	0.0249 (5)	0.0267 (5)	0.0179 (4)	0.0022 (4)	0.0001 (3)	−0.0014 (3)
C2	0.0187 (4)	0.0245 (5)	0.0211 (4)	0.0011 (3)	−0.0011 (3)	−0.0036 (3)
C3	0.0209 (4)	0.0301 (5)	0.0218 (4)	0.0016 (4)	0.0001 (3)	−0.0058 (4)
C4	0.0223 (4)	0.0286 (5)	0.0278 (5)	0.0021 (4)	−0.0002 (4)	−0.0109 (4)
C5	0.0234 (5)	0.0220 (5)	0.0325 (5)	−0.0012 (4)	0.0005 (4)	−0.0084 (4)
C6	0.0194 (4)	0.0218 (5)	0.0269 (5)	−0.0022 (3)	0.0013 (3)	−0.0053 (4)
C7	0.0241 (5)	0.0208 (5)	0.0334 (5)	−0.0028 (4)	0.0052 (4)	−0.0024 (4)
C8	0.0197 (4)	0.0309 (5)	0.0239 (5)	−0.0021 (4)	0.0020 (3)	0.0026 (4)
C9	0.0190 (4)	0.0340 (5)	0.0189 (4)	0.0008 (4)	0.0009 (3)	−0.0006 (4)
C10	0.0233 (5)	0.0522 (7)	0.0254 (5)	−0.0044 (5)	0.0061 (4)	−0.0067 (5)
C11	0.0255 (5)	0.0603 (8)	0.0357 (6)	0.0018 (5)	0.0099 (4)	−0.0177 (6)
C12	0.0280 (5)	0.0441 (7)	0.0332 (6)	0.0112 (5)	0.0014 (4)	−0.0141 (5)
C13	0.0260 (5)	0.0299 (5)	0.0218 (4)	0.0099 (4)	−0.0017 (4)	−0.0048 (4)
C14	0.0375 (6)	0.0245 (5)	0.0231 (5)	0.0103 (4)	−0.0013 (4)	−0.0029 (4)
C15	0.0412 (6)	0.0179 (4)	0.0219 (4)	−0.0010 (4)	0.0004 (4)	0.0022 (3)
C16	0.0281 (5)	0.0200 (5)	0.0230 (4)	−0.0040 (4)	−0.0017 (4)	0.0036 (3)
C17	0.0330 (5)	0.0279 (5)	0.0338 (5)	−0.0085 (4)	0.0005 (4)	0.0108 (4)
C18	0.0250 (5)	0.0423 (7)	0.0383 (6)	−0.0051 (4)	0.0060 (4)	0.0166 (5)
C19	0.0203 (4)	0.0365 (6)	0.0304 (5)	0.0028 (4)	0.0040 (4)	0.0096 (4)
C20	0.0183 (4)	0.0236 (5)	0.0220 (4)	0.0000 (3)	−0.0007 (3)	0.0037 (3)
C21	0.0180 (4)	0.0229 (5)	0.0229 (4)	0.0024 (3)	0.0001 (3)	0.0015 (3)
C22	0.0510 (7)	0.0238 (5)	0.0287 (5)	0.0041 (5)	0.0082 (5)	0.0031 (4)
C23	0.0808 (10)	0.0273 (6)	0.0419 (7)	−0.0084 (6)	0.0309 (7)	−0.0045 (5)
C24	0.0320 (5)	0.0221 (5)	0.0288 (5)	0.0063 (4)	0.0056 (4)	0.0017 (4)
C25	0.0420 (6)	0.0298 (6)	0.0350 (6)	0.0093 (5)	0.0095 (5)	−0.0033 (4)

O1—C1	1.2064 (12)	C8—C9	1.5063 (15)
O2—C1	1.3289 (12)	C9—C10	1.3898 (14)
O2—C22	1.4603 (13)	C10—C11	1.3825 (18)
O3—C7	1.2100 (13)	C10—H10	0.9500
O4—C8	1.2109 (13)	C11—C12	1.3854 (19)
O5—C14	1.2123 (13)	C11—H11	0.9500
O6—C15	1.2131 (13)	C12—C13	1.3930 (15)
O7—C21	1.2034 (12)	C12—H12	0.9500
O8—C21	1.3434 (12)	C13—C14	1.5052 (16)
O8—C24	1.4671 (12)	C15—C16	1.5068 (15)
N1—C2	1.3382 (13)	C16—C17	1.3880 (15)
N1—C6	1.3401 (13)	C17—C18	1.3809 (17)
N2—C7	1.3760 (13)	C17—H17	0.9500
N2—C8	1.3809 (13)	C18—C19	1.3893 (16)
N2—H2	0.878 (15)	C18—H18	0.9500
N3—C13	1.3348 (13)	C19—C20	1.3924 (14)
N3—C9	1.3354 (13)	C19—H19	0.9500
N4—C15	1.3732 (14)	C20—C21	1.5057 (13)
N4—C14	1.3796 (14)	C22—C23	1.4949 (18)
N4—H4	0.885 (14)	C22—H22A	0.9900
N5—C16	1.3364 (12)	C22—H22B	0.9900
N5—C20	1.3384 (13)	C23—H23A	0.9800
C1—C2	1.5064 (14)	C23—H23B	0.9800
C2—C3	1.3979 (13)	C23—H23C	0.9800
C3—C4	1.3882 (15)	C24—C25	1.5064 (14)
C3—H3	0.9500	C24—H24A	0.9900
C4—C5	1.3859 (15)	C24—H24B	0.9900
C4—H4A	0.9500	C25—H25A	0.9800
C5—C6	1.3895 (14)	C25—H25B	0.9800
C5—H5	0.9500	C25—H25C	0.9800
C6—C7	1.5086 (14)
C1—O2—C22	116.47 (8)	C12—C13—C14	122.10 (10)
C21—O8—C24	114.60 (8)	O5—C14—N4	125.50 (11)
C2—N1—C6	117.56 (8)	O5—C14—C13	123.18 (10)
C7—N2—C8	129.30 (9)	N4—C14—C13	111.32 (8)
C7—N2—H2	114.2 (9)	O6—C15—N4	125.43 (11)
C8—N2—H2	116.3 (9)	O6—C15—C16	122.08 (10)
C13—N3—C9	118.83 (9)	N4—C15—C16	112.49 (8)
C15—N4—C14	129.10 (9)	N5—C16—C17	123.57 (10)
C15—N4—H4	115.0 (9)	N5—C16—C15	116.50 (9)
C14—N4—H4	115.7 (9)	C17—C16—C15	119.90 (9)
C16—N5—C20	117.56 (9)	C18—C17—C16	118.41 (10)
O1—C1—O2	125.14 (10)	C18—C17—H17	120.8
O1—C1—C2	124.11 (9)	C16—C17—H17	120.8
O2—C1—C2	110.75 (8)	C17—C18—C19	118.91 (10)
N1—C2—C3	122.96 (9)	C17—C18—H18	120.5
N1—C2—C1	114.99 (8)	C19—C18—H18	120.5
C3—C2—C1	122.04 (9)	C18—C19—C20	118.59 (10)
C4—C3—C2	118.48 (10)	C18—C19—H19	120.7
C4—C3—H3	120.8	C20—C19—H19	120.7
C2—C3—H3	120.8	N5—C20—C19	122.90 (9)
C5—C4—C3	119.04 (9)	N5—C20—C21	114.16 (8)
C5—C4—H4A	120.5	C19—C20—C21	122.92 (9)
C3—C4—H4A	120.5	O7—C21—O8	124.66 (9)
C4—C5—C6	118.31 (10)	O7—C21—C20	123.41 (9)
C4—C5—H5	120.8	O8—C21—C20	111.94 (8)
C6—C5—H5	120.8	O2—C22—C23	106.44 (9)
N1—C6—C5	123.57 (9)	O2—C22—H22A	110.4
N1—C6—C7	116.89 (8)	C23—C22—H22A	110.4
C5—C6—C7	119.53 (9)	O2—C22—H22B	110.4
O3—C7—N2	125.58 (10)	C23—C22—H22B	110.4
O3—C7—C6	122.35 (9)	H22A—C22—H22B	108.6
N2—C7—C6	112.06 (8)	C22—C23—H23A	109.5
O4—C8—N2	126.13 (10)	C22—C23—H23B	109.5
O4—C8—C9	122.81 (9)	H23A—C23—H23B	109.5
N2—C8—C9	111.02 (8)	C22—C23—H23C	109.5
N3—C9—C10	122.87 (10)	H23A—C23—H23C	109.5
N3—C9—C8	115.64 (8)	H23B—C23—H23C	109.5
C10—C9—C8	121.45 (10)	O8—C24—C25	108.13 (8)
C11—C10—C9	117.80 (11)	O8—C24—H24A	110.1
C11—C10—H10	121.1	C25—C24—H24A	110.1
C9—C10—H10	121.1	O8—C24—H24B	110.1
C10—C11—C12	120.02 (10)	C25—C24—H24B	110.1
C10—C11—H11	120.0	H24A—C24—H24B	108.4
C12—C11—H11	120.0	C24—C25—H25A	109.5
C11—C12—C13	118.10 (11)	C24—C25—H25B	109.5
C11—C12—H12	121.0	H25A—C25—H25B	109.5
C13—C12—H12	121.0	C24—C25—H25C	109.5
N3—C13—C12	122.34 (11)	H25A—C25—H25C	109.5
N3—C13—C14	115.55 (9)	H25B—C25—H25C	109.5
C22—O2—C1—O1	−3.25 (15)	C9—N3—C13—C12	−0.98 (14)
C22—O2—C1—C2	177.85 (8)	C9—N3—C13—C14	178.44 (8)
C6—N1—C2—C3	0.73 (13)	C11—C12—C13—N3	1.89 (16)
C6—N1—C2—C1	−179.54 (8)	C11—C12—C13—C14	−177.48 (10)
O1—C1—C2—N1	−15.36 (14)	C15—N4—C14—O5	−0.58 (18)
O2—C1—C2—N1	163.55 (8)	C15—N4—C14—C13	179.72 (9)
O1—C1—C2—C3	164.37 (10)	N3—C13—C14—O5	162.22 (10)
O2—C1—C2—C3	−16.71 (12)	C12—C13—C14—O5	−18.36 (16)
N1—C2—C3—C4	1.73 (14)	N3—C13—C14—N4	−18.07 (12)
C1—C2—C3—C4	−177.98 (8)	C12—C13—C14—N4	161.35 (9)
C2—C3—C4—C5	−2.40 (14)	C14—N4—C15—O6	3.77 (18)
C3—C4—C5—C6	0.72 (14)	C14—N4—C15—C16	−175.83 (9)
C2—N1—C6—C5	−2.58 (14)	C20—N5—C16—C17	−2.57 (14)
C2—N1—C6—C7	176.59 (8)	C20—N5—C16—C15	175.38 (8)
C4—C5—C6—N1	1.87 (15)	O6—C15—C16—N5	178.10 (10)
C4—C5—C6—C7	−177.27 (9)	N4—C15—C16—N5	−2.29 (12)
C8—N2—C7—O3	−8.40 (18)	O6—C15—C16—C17	−3.88 (15)
C8—N2—C7—C6	170.93 (9)	N4—C15—C16—C17	175.74 (9)
N1—C6—C7—O3	178.12 (10)	N5—C16—C17—C18	2.05 (16)
C5—C6—C7—O3	−2.68 (15)	C15—C16—C17—C18	−175.83 (10)
N1—C6—C7—N2	−1.24 (12)	C16—C17—C18—C19	0.37 (16)
C5—C6—C7—N2	177.96 (9)	C17—C18—C19—C20	−2.07 (16)
C7—N2—C8—O4	4.13 (18)	C16—N5—C20—C19	0.70 (14)
C7—N2—C8—C9	−173.76 (9)	C16—N5—C20—C21	179.34 (8)
C13—N3—C9—C10	−0.73 (14)	C18—C19—C20—N5	1.58 (15)
C13—N3—C9—C8	177.19 (8)	C18—C19—C20—C21	−176.94 (9)
O4—C8—C9—N3	167.30 (9)	C24—O8—C21—O7	−1.92 (13)
N2—C8—C9—N3	−14.72 (12)	C24—O8—C21—C20	178.12 (8)
O4—C8—C9—C10	−14.75 (15)	N5—C20—C21—O7	−19.00 (13)
N2—C8—C9—C10	163.23 (9)	C19—C20—C21—O7	159.64 (10)
N3—C9—C10—C11	1.43 (15)	N5—C20—C21—O8	160.96 (8)
C8—C9—C10—C11	−176.37 (10)	C19—C20—C21—O8	−20.40 (13)
C9—C10—C11—C12	−0.44 (17)	C1—O2—C22—C23	170.48 (10)
C10—C11—C12—C13	−1.12 (17)	C21—O8—C24—C25	168.94 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N3	0.885 (14)	2.153 (14)	2.6131 (13)	111.7 (11)
N4—H4···N5	0.885 (14)	2.158 (14)	2.6297 (12)	112.8 (11)
N2—H2···N3	0.878 (15)	2.148 (14)	2.6006 (12)	111.4 (11)
N2—H2···N1	0.878 (15)	2.151 (14)	2.6329 (12)	114.0 (11)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N3	0.885 (14)	2.153 (14)	2.6131 (13)	111.7 (11)
N4—H4⋯N5	0.885 (14)	2.158 (14)	2.6297 (12)	112.8 (11)
N2—H2⋯N3	0.878 (15)	2.148 (14)	2.6006 (12)	111.4 (11)
N2—H2⋯N1	0.878 (15)	2.151 (14)	2.6329 (12)	114.0 (11)