Syntheses, structures and properties of two new isostructural zinc(II) complexes based on 1-[(benzotriazol-1-yl)meth­yl]-1H-imidazole

Due to their strong coordination ability and the diversities of their coordination modes, N-heterocyclic organic compounds are used extensively as ligands for the construction of complexes with fascinating structures and potential applications in many fields. Two new complexes, namely bis­{1-[(benzotriazol-1-yl)meth­yl]-1H-imidazole-κN³}di­bromido­zinc(II), [ZnBr₂(C₁₀H₉N₅)₂], (I), and bis­{1-[(benzotriazol-1-yl)meth­yl]-1H-imidazole-κN³}di­iodido­zinc(II), [ZnI₂(C₁₀H₉N₅)₂], (II), have been synthesized by reaction of the unsymmetrical N-heterocyclic ligand 1-[(benzotriazol-1-yl)meth­yl]-1H-imidazole (bmi) with Zn(acetate)₂ in the presence of KBr or KI. Single-crystal X-ray diffraction analysis shows that both complexes exhibit a mononuclear structure, in which the bmi ligands coordinate to the central metal ion in a monodentate mode. In the solid state, both complexes possess a three-dimensional network formed by hydrogen bonds and π–π inter­actions. In addition, the IR spectroscopic properties, PXRD patterns and fluorescence properties of both complexes have been investigated.

Computing details

For both compounds, data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear (Rigaku/MSC, 2004); data reduction: CrystalClear (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).

(I) Bis{1-[(benzotriazol-1-yl)methyl]-1H-imidazole-κN³}dibromidozinc(II)

Crystal data

[ZnBr2(C10H9N5)2]	Dx = 1.801 Mg m^−3
Mr = 623.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 5172 reflections
a = 11.498 (2) Å	θ = 2.1–27.8°
b = 11.715 (2) Å	µ = 4.58 mm^−1
c = 17.071 (3) Å	T = 293 K
V = 2299.4 (8) Å^3	Prism, colourless
Z = 4	0.17 × 0.16 × 0.12 mm
F(000) = 1232

Data collection

Rigaku Saturn diffractometer	2271 independent reflections
Radiation source: fine-focus sealed tube	1977 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.044
ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	h = −13→14
Tmin = 0.742, Tmax = 1.000	k = −10→14
14163 measured reflections	l = −16→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.0336P)^2 + 1.2668P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
2271 reflections	Δρmax = 0.45 e Å^−3
150 parameters	Δρmin = −0.42 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
Zn1	0.0000	0.36417 (5)	0.2500	0.03343 (17)
Br1	0.06408 (4)	0.46925 (3)	0.13951 (2)	0.04817 (15)
N1	0.1306 (3)	0.2646 (2)	0.29102 (15)	0.0345 (7)
N2	0.2490 (3)	0.1814 (2)	0.37410 (14)	0.0324 (6)
N3	0.2304 (3)	0.0759 (2)	0.49422 (15)	0.0338 (7)
N4	0.2355 (3)	−0.0394 (2)	0.48559 (18)	0.0458 (8)
N5	0.1587 (3)	−0.0850 (2)	0.53165 (19)	0.0471 (8)
C1	0.1668 (3)	0.2613 (3)	0.36456 (19)	0.0341 (8)
H1A	0.1390	0.3082	0.4043	0.041*
C2	0.1949 (3)	0.1836 (3)	0.2520 (2)	0.0403 (9)
H2A	0.1896	0.1676	0.1988	0.048*
C3	0.2663 (3)	0.1314 (3)	0.3027 (2)	0.0417 (9)
H3A	0.3178	0.0725	0.2915	0.050*
C4	0.3044 (3)	0.1492 (3)	0.44837 (19)	0.0366 (8)
H4A	0.3771	0.1102	0.4376	0.044*
H4B	0.3221	0.2176	0.4781	0.044*
C5	0.1482 (3)	0.1042 (3)	0.54808 (18)	0.0331 (8)
C6	0.1113 (3)	0.2074 (3)	0.58013 (19)	0.0378 (8)
H6A	0.1434	0.2768	0.5649	0.045*
C7	0.0256 (4)	0.2008 (4)	0.6349 (2)	0.0475 (10)
H7A	0.0002	0.2677	0.6588	0.057*
C8	−0.0260 (4)	0.0971 (4)	0.6568 (2)	0.0537 (11)
H8A	−0.0870	0.0972	0.6925	0.064*
C9	0.0119 (4)	−0.0037 (4)	0.6266 (2)	0.0515 (11)
H9A	−0.0209	−0.0727	0.6420	0.062*
C10	0.1019 (3)	0.0002 (3)	0.5716 (2)	0.0376 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0363 (4)	0.0307 (3)	0.0333 (3)	0.000	−0.0025 (2)	0.000
Br1	0.0489 (3)	0.0499 (3)	0.0458 (3)	−0.00021 (19)	0.00781 (18)	0.01271 (18)
N1	0.0373 (18)	0.0321 (16)	0.0340 (16)	−0.0024 (13)	−0.0031 (13)	−0.0019 (12)
N2	0.0313 (17)	0.0323 (15)	0.0337 (16)	0.0021 (13)	−0.0015 (12)	−0.0018 (13)
N3	0.0394 (19)	0.0254 (14)	0.0367 (16)	0.0033 (13)	−0.0054 (13)	0.0008 (12)
N4	0.058 (2)	0.0309 (17)	0.0489 (19)	0.0090 (16)	−0.0114 (17)	−0.0016 (14)
N5	0.058 (2)	0.0282 (16)	0.055 (2)	−0.0007 (16)	−0.0144 (17)	0.0021 (15)
C1	0.036 (2)	0.0305 (18)	0.0360 (19)	0.0001 (15)	0.0006 (15)	−0.0019 (15)
C2	0.041 (2)	0.046 (2)	0.0340 (19)	0.0018 (18)	0.0025 (17)	−0.0060 (17)
C3	0.041 (2)	0.042 (2)	0.042 (2)	0.0104 (18)	0.0038 (17)	−0.0080 (17)
C4	0.033 (2)	0.039 (2)	0.039 (2)	0.0039 (16)	−0.0045 (15)	0.0000 (16)
C5	0.033 (2)	0.0332 (19)	0.0334 (18)	−0.0017 (15)	−0.0082 (15)	0.0043 (15)
C6	0.042 (2)	0.0301 (18)	0.042 (2)	0.0027 (16)	−0.0018 (17)	0.0022 (15)
C7	0.051 (3)	0.049 (2)	0.042 (2)	0.010 (2)	−0.0014 (18)	0.0007 (18)
C8	0.041 (3)	0.075 (3)	0.045 (2)	0.001 (2)	−0.0017 (18)	0.007 (2)
C9	0.047 (3)	0.058 (3)	0.050 (2)	−0.018 (2)	−0.014 (2)	0.023 (2)
C10	0.040 (2)	0.0327 (19)	0.041 (2)	−0.0030 (16)	−0.0141 (17)	0.0056 (16)

Geometric parameters (Å, º)

Zn1—N1	2.026 (3)	C2—C3	1.341 (5)
Zn1—N1^i	2.026 (3)	C2—H2A	0.9300
Zn1—Br1	2.3698 (6)	C3—H3A	0.9300
Zn1—Br1^i	2.3699 (6)	C4—H4A	0.9700
N1—C1	1.323 (4)	C4—H4B	0.9700
N1—C2	1.374 (4)	C5—C10	1.389 (5)
N2—C1	1.340 (4)	C5—C6	1.393 (5)
N2—C3	1.366 (4)	C6—C7	1.361 (5)
N2—C4	1.469 (4)	C6—H6A	0.9300
N3—N4	1.360 (4)	C7—C8	1.403 (6)
N3—C5	1.360 (4)	C7—H7A	0.9300
N3—C4	1.440 (4)	C8—C9	1.359 (6)
N4—N5	1.298 (4)	C8—H8A	0.9300
N5—C10	1.374 (5)	C9—C10	1.398 (6)
C1—H1A	0.9300	C9—H9A	0.9300
N1—Zn1—N1^i	109.71 (16)	N2—C3—H3A	126.5
N1—Zn1—Br1	110.10 (8)	N3—C4—N2	111.4 (3)
N1^i—Zn1—Br1	104.74 (8)	N3—C4—H4A	109.3
N1—Zn1—Br1^i	104.74 (8)	N2—C4—H4A	109.3
N1^i—Zn1—Br1^i	110.10 (8)	N3—C4—H4B	109.3
Br1—Zn1—Br1^i	117.41 (3)	N2—C4—H4B	109.3
C1—N1—C2	105.7 (3)	H4A—C4—H4B	108.0
C1—N1—Zn1	125.3 (2)	N3—C5—C10	104.4 (3)
C2—N1—Zn1	128.9 (2)	N3—C5—C6	133.5 (3)
C1—N2—C3	107.1 (3)	C10—C5—C6	122.0 (3)
C1—N2—C4	126.2 (3)	C7—C6—C5	116.2 (3)
C3—N2—C4	126.6 (3)	C7—C6—H6A	121.9
N4—N3—C5	110.2 (3)	C5—C6—H6A	121.9
N4—N3—C4	120.5 (3)	C6—C7—C8	122.5 (4)
C5—N3—C4	129.3 (3)	C6—C7—H7A	118.7
N5—N4—N3	108.3 (3)	C8—C7—H7A	118.7
N4—N5—C10	109.0 (3)	C9—C8—C7	121.1 (4)
N1—C1—N2	111.0 (3)	C9—C8—H8A	119.5
N1—C1—H1A	124.5	C7—C8—H8A	119.5
N2—C1—H1A	124.5	C8—C9—C10	117.6 (4)
C3—C2—N1	109.3 (3)	C8—C9—H9A	121.2
C3—C2—H2A	125.3	C10—C9—H9A	121.2
N1—C2—H2A	125.3	N5—C10—C5	108.1 (3)
C2—C3—N2	106.9 (3)	N5—C10—C9	131.5 (4)
C2—C3—H3A	126.5	C5—C10—C9	120.4 (4)
C5—N3—N4—N5	0.5 (4)	C4—N3—C5—C10	178.1 (3)
C4—N3—N4—N5	−178.4 (3)	N4—N3—C5—C6	177.4 (4)
N3—N4—N5—C10	−0.2 (4)	C4—N3—C5—C6	−3.8 (6)
C2—N1—C1—N2	−1.0 (4)	N3—C5—C6—C7	−178.9 (4)
Zn1—N1—C1—N2	175.7 (2)	C10—C5—C6—C7	−1.1 (5)
C3—N2—C1—N1	0.2 (4)	C5—C6—C7—C8	−1.9 (6)
C4—N2—C1—N1	−176.4 (3)	C6—C7—C8—C9	3.3 (6)
C1—N1—C2—C3	1.4 (4)	C7—C8—C9—C10	−1.6 (6)
Zn1—N1—C2—C3	−175.2 (3)	N4—N5—C10—C5	−0.2 (4)
N1—C2—C3—N2	−1.3 (4)	N4—N5—C10—C9	179.0 (4)
C1—N2—C3—C2	0.6 (4)	N3—C5—C10—N5	0.5 (4)
C4—N2—C3—C2	177.3 (3)	C6—C5—C10—N5	−177.8 (3)
N4—N3—C4—N2	89.6 (4)	N3—C5—C10—C9	−178.8 (3)
C5—N3—C4—N2	−89.0 (4)	C6—C5—C10—C9	2.8 (5)
C1—N2—C4—N3	78.5 (4)	C8—C9—C10—N5	179.4 (4)
C3—N2—C4—N3	−97.5 (4)	C8—C9—C10—C5	−1.4 (6)
N4—N3—C5—C10	−0.6 (4)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Br1^ii	0.97	3.01	3.951 (4)	163
C4—H4B···N5^iii	0.97	2.50	3.449 (5)	167

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

(II) Bis{1-[(benzotriazol-1-yl)methyl]-1H-imidazole-κN³}diiodidozinc(II)

Crystal data

[ZnI2(C10H9N5)2]	Dx = 1.952 Mg m^−3
Mr = 717.61	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 6875 reflections
a = 11.729 (2) Å	θ = 1.7–28.0°
b = 11.853 (2) Å	µ = 3.56 mm^−1
c = 17.563 (4) Å	T = 293 K
V = 2441.7 (8) Å^3	Prism, colourless
Z = 4	0.16 × 0.13 × 0.08 mm
F(000) = 1376

Data collection

Rigaku Saturn diffractometer	2400 independent reflections
Radiation source: fine-focus sealed tube	2235 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.033
ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	h = −14→14
Tmin = 0.813, Tmax = 1.000	k = −12→14
14216 measured reflections	l = −13→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.064	w = 1/[σ^2(Fo^2) + (0.0216P)^2 + 3.1101P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max = 0.001
2400 reflections	Δρmax = 0.48 e Å^−3
150 parameters	Δρmin = −0.62 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
Zn1	0.0000	0.13958 (5)	0.2500	0.03295 (14)
I1	0.07239 (2)	0.02815 (2)	0.36520 (2)	0.04549 (10)
N1	0.1276 (2)	0.2374 (2)	0.20866 (16)	0.0351 (6)
N2	0.2447 (3)	0.3164 (2)	0.12729 (15)	0.0343 (6)
N3	0.2266 (3)	0.4231 (2)	0.01187 (16)	0.0361 (7)
N4	0.2339 (3)	0.5370 (3)	0.02233 (19)	0.0506 (9)
N5	0.1625 (3)	0.5859 (3)	−0.0232 (2)	0.0565 (10)
C1	0.1626 (3)	0.2395 (3)	0.13763 (19)	0.0369 (8)
H1A	0.1339	0.1933	0.0993	0.044*
C2	0.1920 (3)	0.3170 (3)	0.2461 (2)	0.0467 (9)
H2A	0.1869	0.3337	0.2977	0.056*
C3	0.2636 (4)	0.3670 (3)	0.1966 (2)	0.0478 (10)
H3A	0.3154	0.4243	0.2071	0.057*
C4	0.2979 (3)	0.3478 (3)	0.0548 (2)	0.0400 (8)
H4A	0.3706	0.3839	0.0647	0.048*
H4B	0.3122	0.2802	0.0251	0.048*
C5	0.1478 (3)	0.3994 (3)	−0.04272 (19)	0.0359 (8)
C6	0.1064 (4)	0.5050 (3)	−0.0647 (2)	0.0452 (10)
C7	0.0211 (4)	0.5127 (4)	−0.1207 (2)	0.0611 (14)
H7A	−0.0089	0.5819	−0.1353	0.073*
C8	−0.0156 (4)	0.4150 (5)	−0.1524 (3)	0.0633 (13)
H8A	−0.0724	0.4177	−0.1892	0.076*
C9	0.0293 (4)	0.3101 (4)	−0.1314 (2)	0.0574 (11)
H9A	0.0031	0.2455	−0.1558	0.069*
C10	0.1101 (3)	0.3002 (3)	−0.0764 (2)	0.0450 (9)
H10A	0.1389	0.2303	−0.0620	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0337 (3)	0.0335 (3)	0.0317 (3)	0.000	0.0007 (2)	0.000
I1	0.04298 (16)	0.05144 (18)	0.04206 (15)	0.00149 (12)	−0.00946 (11)	0.01041 (11)
N1	0.0351 (16)	0.0359 (16)	0.0343 (15)	−0.0035 (13)	0.0021 (12)	−0.0005 (13)
N2	0.0355 (16)	0.0330 (15)	0.0344 (15)	−0.0068 (13)	0.0040 (12)	−0.0018 (13)
N3	0.0437 (18)	0.0248 (14)	0.0399 (16)	−0.0059 (13)	0.0101 (14)	−0.0014 (13)
N4	0.066 (2)	0.0301 (17)	0.056 (2)	−0.0105 (16)	0.0207 (18)	−0.0060 (15)
N5	0.071 (3)	0.0332 (19)	0.065 (2)	0.0056 (18)	0.026 (2)	0.0072 (18)
C1	0.041 (2)	0.0325 (19)	0.0366 (18)	−0.0052 (16)	0.0020 (16)	−0.0028 (16)
C2	0.048 (2)	0.056 (2)	0.0353 (19)	−0.0120 (19)	0.0009 (17)	−0.0099 (18)
C3	0.048 (2)	0.052 (2)	0.044 (2)	−0.0146 (19)	−0.0017 (18)	−0.0121 (19)
C4	0.034 (2)	0.042 (2)	0.044 (2)	−0.0075 (16)	0.0074 (16)	−0.0032 (17)
C5	0.037 (2)	0.033 (2)	0.0381 (18)	0.0008 (15)	0.0106 (15)	0.0047 (15)
C6	0.046 (2)	0.039 (2)	0.051 (2)	0.0071 (18)	0.0232 (19)	0.0119 (19)
C7	0.058 (3)	0.066 (3)	0.060 (3)	0.028 (2)	0.022 (2)	0.028 (2)
C8	0.049 (3)	0.091 (4)	0.049 (2)	0.010 (3)	0.001 (2)	0.011 (3)
C9	0.056 (3)	0.065 (3)	0.051 (2)	−0.008 (2)	−0.002 (2)	0.001 (2)
C10	0.046 (2)	0.040 (2)	0.048 (2)	−0.0040 (18)	0.0015 (18)	0.0004 (18)

Geometric parameters (Å, º)

Zn1—N1^i	2.028 (3)	C2—C3	1.346 (5)
Zn1—N1	2.028 (3)	C2—H2A	0.9300
Zn1—I1^i	2.5610 (5)	C3—H3A	0.9300
Zn1—I1	2.5611 (5)	C4—H4A	0.9700
N1—C1	1.313 (4)	C4—H4B	0.9700
N1—C2	1.377 (4)	C5—C10	1.389 (5)
N2—C1	1.339 (4)	C5—C6	1.396 (5)
N2—C3	1.375 (4)	C6—C7	1.405 (7)
N2—C4	1.465 (4)	C7—C8	1.355 (7)
N3—C5	1.361 (5)	C7—H7A	0.9300
N3—N4	1.365 (4)	C8—C9	1.399 (7)
N3—C4	1.438 (5)	C8—H8A	0.9300
N4—N5	1.295 (5)	C9—C10	1.359 (6)
N5—C6	1.374 (6)	C9—H9A	0.9300
C1—H1A	0.9300	C10—H10A	0.9300
N1^i—Zn1—N1	110.27 (16)	N2—C3—H3A	126.9
N1^i—Zn1—I1^i	109.45 (8)	N3—C4—N2	111.5 (3)
N1—Zn1—I1^i	104.87 (8)	N3—C4—H4A	109.3
N1^i—Zn1—I1	104.87 (8)	N2—C4—H4A	109.3
N1—Zn1—I1	109.45 (8)	N3—C4—H4B	109.3
I1^i—Zn1—I1	117.91 (3)	N2—C4—H4B	109.3
C1—N1—C2	105.7 (3)	H4A—C4—H4B	108.0
C1—N1—Zn1	125.5 (2)	N3—C5—C10	133.7 (3)
C2—N1—Zn1	128.8 (2)	N3—C5—C6	104.3 (3)
C1—N2—C3	107.0 (3)	C10—C5—C6	122.0 (4)
C1—N2—C4	126.7 (3)	N5—C6—C5	108.2 (4)
C3—N2—C4	126.1 (3)	N5—C6—C7	131.8 (4)
C5—N3—N4	110.0 (3)	C5—C6—C7	120.0 (4)
C5—N3—C4	129.5 (3)	C8—C7—C6	117.2 (4)
N4—N3—C4	120.5 (3)	C8—C7—H7A	121.4
N5—N4—N3	108.6 (3)	C6—C7—H7A	121.4
N4—N5—C6	108.9 (3)	C7—C8—C9	122.1 (4)
N1—C1—N2	111.5 (3)	C7—C8—H8A	118.9
N1—C1—H1A	124.3	C9—C8—H8A	118.9
N2—C1—H1A	124.3	C10—C9—C8	121.7 (5)
C3—C2—N1	109.6 (3)	C10—C9—H9A	119.1
C3—C2—H2A	125.2	C8—C9—H9A	119.1
N1—C2—H2A	125.2	C9—C10—C5	116.9 (4)
C2—C3—N2	106.2 (3)	C9—C10—H10A	121.6
C2—C3—H3A	126.9	C5—C10—H10A	121.6
C5—N3—N4—N5	0.4 (4)	C4—N3—C5—C10	−1.3 (6)
C4—N3—N4—N5	179.3 (3)	N4—N3—C5—C6	−0.5 (4)
N3—N4—N5—C6	0.0 (4)	C4—N3—C5—C6	−179.4 (3)
C2—N1—C1—N2	−0.6 (4)	N4—N5—C6—C5	−0.3 (4)
Zn1—N1—C1—N2	177.1 (2)	N4—N5—C6—C7	179.4 (4)
C3—N2—C1—N1	0.0 (4)	N3—C5—C6—N5	0.5 (4)
C4—N2—C1—N1	−175.3 (3)	C10—C5—C6—N5	−177.9 (3)
C1—N1—C2—C3	0.9 (5)	N3—C5—C6—C7	−179.3 (3)
Zn1—N1—C2—C3	−176.7 (3)	C10—C5—C6—C7	2.3 (5)
N1—C2—C3—N2	−0.9 (5)	N5—C6—C7—C8	178.8 (4)
C1—N2—C3—C2	0.6 (4)	C5—C6—C7—C8	−1.5 (6)
C4—N2—C3—C2	175.9 (4)	C6—C7—C8—C9	−0.5 (6)
C5—N3—C4—N2	−93.0 (4)	C7—C8—C9—C10	1.9 (7)
N4—N3—C4—N2	88.3 (4)	C8—C9—C10—C5	−1.1 (6)
C1—N2—C4—N3	78.9 (4)	N3—C5—C10—C9	−178.9 (4)
C3—N2—C4—N3	−95.4 (4)	C6—C5—C10—C9	−1.0 (6)
N4—N3—C5—C10	177.6 (4)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···I1^ii	0.97	3.17	4.112 (4)	165
C4—H4B···N5^iii	0.97	2.47	3.424 (5)	167

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