N-(2-Iodo­phen­yl)benzene­carbox­imid­amide

Zhang, Y.; Wang, D.; Zhang, H.-L.; Wang, Y.-G.

doi:10.1107/S160053681200596X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o726

doi:10.1107/S160053681200596X

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N-(2-Iodophenyl)benzenecarboximidamide

Yin-jun Zhang,^a Dong Wang,^a Hai-Liang Zhang ^b and Yu-Guang Wang ^a ^*

^aCollege of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, and ^bZhejiang SiXian Pharmaceutical Co. Ltd, ShaoXing 312065, People's Republic of China
^*Correspondence e-mail: yuguangw@zjut.edu.cn

(Received 26 January 2012; accepted 10 February 2012; online 17 February 2012)

The title compound, C₁₃H₁₁IN₂, crystallizes with two independent molecules (A and B) in the asymmetric unit. The two aromatic rings are inclined to one another by 73.3 (2)° in molecule A, and by 74.4 (1)° in molecule B. In molecule A, the iodophenyl and the phenyl rings are inlclined to the N=C—N plane by 88.0 (4) and 19.0 (4)°, respectively. In molecule B the corresponding angles are 85.0 (4) and 20.7 (4)°, respectively. In the crystal, the two molecules are not parallel but have a dihedral angle between the iodophenyl rings of 8.6 (1)°, and 44.5 (2)° between the phenyl rings. The A and B molecules are linked vvia N—H⋯N hydrogen bonds to form –A–B–A–B– chains propagating along direction [100].

Related literature

For the application of amidines in the synthesis of heterocyclic compounds, see: Attanasi et al. (2010 ); Bhosale et al. (2010 ); Deng & Mani (2010 ); Wang et al. (2011 ); Ohta et al. (2010 ). For details of the synthetic procedure to yield the title compound, see: Ma et al. (2011 ); Cortes-Salva et al. (2011 ).

Experimental

Crystal data

C₁₃H₁₁IN₂
M_r = 322.14
Triclinic, $[P \overline 1]$
a = 10.411 (3) Å
b = 11.024 (3) Å
c = 11.534 (3) Å
α = 95.501 (3)°
β = 95.065 (3)°
γ = 102.986 (3)°
V = 1275.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.49 mm⁻¹
T = 296 K
0.49 × 0.44 × 0.30 mm

Data collection

CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.376, T_max = 0.523
9707 measured reflections
4716 independent reflections
4076 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.079
S = 1.04
4716 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.94 e Å⁻³
Δρ_min = −1.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N3ⁱ	0.86	2.25	3.057 (4)	156
N4—H4B⋯N1ⁱⁱ	0.86	2.24	3.027 (4)	151
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681200596X/im2355sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200596X/im2355Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681200596X/im2355Isup3.cml

checkCIF report

Comment top

Benzamidines and their derivatives have attracted our attention because of their application in the synthesis of heterocyclic compounds (Attanasi et al. 2010, Bhosale et al. 2010, Deng & Mani et al. 20109, Wang et al. 2011, Ohta et al. 2010). We report here the crystal structure of the title compound (Fig. 1).

The asymmetric unit of the title compound contains two crystallographically independent molecules (A and B). Concerning the carbon atoms, molecule A is made up from C1 to C13 and molecule B is made up from C14 to C26. In both molecules the bond lengths and angles are generally within normal ranges. The bond lengths N1-C7 (1.293 (4) Å) and N3-C20 (1.293 (3) Å) displays double bond character, while the distances N2-C20 1.350 (5) Å and N4-C20 1.352 (5) Å are indicative of C–N single bonds. The two molecules are not parallel so that torsion angles of 8.6 (1)° between the two iodo-phenyl groups and 44.5 (2)° between both phenyl substituents, respectively, are observed. In molecule A, the planar benzene ring (C8-C13) and the iodine-substituted benzene ring (C1-C6) form a dihedral angle of 73.3 (2)°. The NH₂ group is twisted away from the plane of the adjacent benzene ring with a dihedral angle between the N-C bond of the NH₂ group and the plane of the adjacent phenyl ring of 18.5 (1)°. The amidine plane and both benzene rings are not coplanar showing dihedral angles of the amidine plane (N1/C7/N2) with respect to the iodine-substituted benzene ring (C1-C6) and the second benzene ring (C8-C13) of 88.2 (2)° and 51.0 (1)°, respectively. In molecule B, the planar benzene ring (C21-C26) and the iodine-substituted benzene ring (C14-C19) form a dihedral angle of 74.4 (1)°. The NH₂ group also is twisted away from the plane of the adjacent benzene ring with a dihedral angle between the N-C bond of the NH₂ group and the plane of the adjacent phenyl ring of 20.7 (2)°. The amidine plane in molecule B and both benzene rings are not coplanar showing dihedral angles of the amidine plane (N3/C20/N4) with respect to the iodine-substituted benzene ring (C14-C19) and the second benzene ring (C21-C26) of 95.1 (3)° and 20.7 (2)°, respectively. In the crystal structure intramolecular N—H···N (N2—H2B···N3 and N4—H4B···N1) hydrogen bonds exist (Table 1).

Related literature top

For the application of amidines in the synthesis of heterocyclic compounds, see: Attanasi et al. (2010); Bhosale et al. (2010); Deng & Mani (2010); Wang et al. (2011); Ohta et al. (2010). For details of the synthetic procedure to yield the title compound, see: Ma et al. (2011); Cortes-Salva et al. (2011).

Experimental top

The title compound was produced according to a methodology already described in the literature (Ma et al. 2011, Cortes-Salva et al. 2011): A round bottom flask (100 mL in volume) was charged with NaH (60% in mineral oil) (360 mg, 15.0 mmol, 60%, 1.5 equiv). Under a stream of nitrogen, DMSO (10 mL) was added, and the resulting suspension was cooled with an ice-water bath prior to the addition of the 2-iodo-phenylamine (11.0 mmol, 1.1 equiv) and benzonitrile (10.0 mmol). The mixture was kept at 0 ° for 50 min and then stirred at room temperature until the starting material was consumed as monitored by TLC analysis. Ice-water (50 mL) was added while maintaining vigorous stirring. When the amidine precipitated upon addition of water, the solid was filtered off and dissolved in EtOAc (20 mL). The aqueous layer was extracted with EtOAc (3 × 20 mL). The extracts were combined and washed with water (2 × 50 mL). The organic layer was dried over Na₂SO₄, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (yield: 75%; m.p. 389-391 K; MS (EI, 70V): 322 (M⁺); ¹H NMR (CDCl₃, 400 MHz): δ = 7.88-7.86 (m, 2H), 7.47-7.05 (m, 5H), 7.47-7.05 (m, 2H), 4.86 (s, 2H)). The title compound was recrystallized from CH₂Cl₂ at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the two symmetry independent molecules of the title compound showing the atom numbering scheme and thermal ellipsoids at the 50% probability level.

N-(2-Iodophenyl)benzenecarboximidamide top

Crystal data top

C₁₃H₁₁IN₂	Z = 4
M_r = 322.14	F(000) = 624
Triclinic, P1	D_x = 1.677 Mg m⁻³
Hall symbol: -P 1	Melting point = 389–391 K
a = 10.411 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.024 (3) Å	Cell parameters from 5918 reflections
c = 11.534 (3) Å	θ = 0.0–0.0°
α = 95.501 (3)°	µ = 2.49 mm⁻¹
β = 95.065 (3)°	T = 296 K
γ = 102.986 (3)°	Block, colourless
V = 1275.7 (6) Å³	0.49 × 0.44 × 0.30 mm

Data collection top

CCD area-detector diffractometer	4716 independent reflections
Radiation source: fine-focus sealed tube	4076 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.376, T_max = 0.523	k = −13→13
9707 measured reflections	l = −13→13

Refinement top

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0273P)² + 1.8412P] where P = (F_o² + 2F_c²)/3
4716 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.94 e Å⁻³
0 restraints	Δρ_min = −1.34 e Å⁻³

Crystal data top

C₁₃H₁₁IN₂	γ = 102.986 (3)°
M_r = 322.14	V = 1275.7 (6) Å³
Triclinic, P1	Z = 4
a = 10.411 (3) Å	Mo Kα radiation
b = 11.024 (3) Å	µ = 2.49 mm⁻¹
c = 11.534 (3) Å	T = 296 K
α = 95.501 (3)°	0.49 × 0.44 × 0.30 mm
β = 95.065 (3)°

Data collection top

CCD area-detector diffractometer	4716 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4076 reflections with I > 2σ(I)
T_min = 0.376, T_max = 0.523	R_int = 0.013
9707 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.04	Δρ_max = 0.94 e Å⁻³
4716 reflections	Δρ_min = −1.34 e Å⁻³
289 parameters

Special details top

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.

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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1631 (3)	0.3372 (3)	0.1714 (3)	0.0462 (7)
C2	0.1131 (3)	0.2143 (3)	0.1182 (3)	0.0409 (7)
C3	0.0759 (3)	0.1972 (3)	−0.0023 (3)	0.0530 (8)
H3	0.0421	0.1164	−0.0402	0.064*
C4	0.0882 (5)	0.2975 (4)	−0.0663 (4)	0.0728 (11)
H4	0.0639	0.2838	−0.1469	0.087*
C5	0.1365 (5)	0.4185 (4)	−0.0115 (4)	0.0751 (12)
H5	0.1441	0.4862	−0.0549	0.090*
C6	0.1731 (4)	0.4381 (4)	0.1069 (4)	0.0629 (10)
H6	0.2048	0.5194	0.1442	0.075*
C7	0.1828 (3)	0.0559 (3)	0.2085 (3)	0.0390 (6)
C8	0.1576 (3)	−0.0507 (3)	0.2811 (3)	0.0397 (6)
C9	0.0539 (3)	−0.0646 (3)	0.3501 (3)	0.0510 (8)
H9	0.0006	−0.0073	0.3512	0.061*
C10	0.0289 (4)	−0.1629 (4)	0.4170 (3)	0.0618 (10)
H10	−0.0416	−0.1715	0.4622	0.074*
C11	0.1071 (4)	−0.2484 (4)	0.4176 (4)	0.0633 (10)
H11	0.0905	−0.3138	0.4636	0.076*
C12	0.2095 (4)	−0.2359 (4)	0.3499 (4)	0.0707 (11)
H12	0.2628	−0.2933	0.3497	0.085*
C13	0.2346 (4)	−0.1383 (4)	0.2812 (4)	0.0620 (10)
H13	0.3039	−0.1315	0.2347	0.074*
C14	0.4353 (3)	1.2019 (3)	0.7427 (3)	0.0515 (8)
C15	0.4541 (3)	1.1218 (3)	0.8267 (3)	0.0405 (7)
C16	0.5055 (3)	1.1761 (3)	0.9409 (3)	0.0529 (8)
H16	0.5201	1.1250	0.9978	0.063*
C17	0.5348 (4)	1.3047 (4)	0.9701 (4)	0.0737 (12)
H17	0.5680	1.3395	1.0466	0.088*
C18	0.5148 (5)	1.3808 (4)	0.8862 (5)	0.0827 (14)
H18	0.5349	1.4673	0.9060	0.099*
C19	0.4654 (4)	1.3303 (4)	0.7728 (5)	0.0722 (12)
H19	0.4522	1.3826	0.7164	0.087*
C20	0.3135 (3)	0.9233 (3)	0.7895 (3)	0.0398 (7)
C21	0.2872 (3)	0.7878 (3)	0.7459 (3)	0.0418 (7)
C22	0.3741 (4)	0.7450 (4)	0.6769 (3)	0.0574 (9)
H22	0.4484	0.8012	0.6586	0.069*
C23	0.3509 (4)	0.6196 (4)	0.6351 (4)	0.0738 (12)
H23	0.4107	0.5915	0.5900	0.089*
C24	0.2400 (4)	0.5355 (4)	0.6594 (4)	0.0672 (11)
H24	0.2248	0.4511	0.6309	0.081*
C25	0.1529 (4)	0.5765 (4)	0.7255 (4)	0.0629 (10)
H25	0.0772	0.5202	0.7411	0.075*
C26	0.1762 (4)	0.7017 (3)	0.7698 (3)	0.0550 (8)
H26	0.1168	0.7283	0.8162	0.066*
I1	0.22107 (3)	0.37212 (3)	0.35229 (2)	0.07680 (12)
I2	0.36281 (3)	1.12543 (3)	0.56938 (2)	0.08108 (12)
N1	0.0885 (2)	0.1116 (2)	0.1848 (2)	0.0423 (6)
N2	0.3033 (3)	0.0867 (3)	0.1700 (3)	0.0553 (8)
H2A	0.3209	0.1467	0.1271	0.066*
H2B	0.3624	0.0464	0.1884	0.066*
N3	0.4332 (2)	0.9910 (2)	0.7956 (2)	0.0410 (6)
N4	0.2101 (3)	0.9688 (3)	0.8219 (3)	0.0557 (7)
H4A	0.2222	1.0466	0.8482	0.067*
H4B	0.1323	0.9198	0.8161	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0438 (17)	0.0485 (18)	0.0445 (17)	0.0066 (14)	0.0000 (14)	0.0103 (14)
C2	0.0277 (14)	0.0447 (17)	0.0514 (18)	0.0095 (12)	0.0051 (12)	0.0091 (14)
C3	0.052 (2)	0.051 (2)	0.054 (2)	0.0092 (16)	0.0055 (16)	0.0035 (16)
C4	0.087 (3)	0.081 (3)	0.046 (2)	0.011 (2)	−0.002 (2)	0.016 (2)
C5	0.099 (3)	0.062 (3)	0.062 (3)	0.008 (2)	−0.002 (2)	0.031 (2)
C6	0.073 (3)	0.045 (2)	0.064 (2)	0.0025 (18)	−0.0007 (19)	0.0133 (17)
C7	0.0287 (14)	0.0407 (16)	0.0466 (17)	0.0072 (12)	0.0035 (12)	0.0039 (13)
C8	0.0328 (15)	0.0406 (16)	0.0446 (16)	0.0085 (12)	0.0006 (12)	0.0045 (13)
C9	0.0469 (18)	0.058 (2)	0.054 (2)	0.0196 (16)	0.0124 (15)	0.0139 (16)
C10	0.061 (2)	0.073 (3)	0.059 (2)	0.0195 (19)	0.0191 (18)	0.0226 (19)
C11	0.065 (2)	0.056 (2)	0.070 (2)	0.0094 (18)	0.0055 (19)	0.0256 (19)
C12	0.067 (3)	0.059 (2)	0.099 (3)	0.029 (2)	0.018 (2)	0.029 (2)
C13	0.051 (2)	0.058 (2)	0.089 (3)	0.0241 (17)	0.025 (2)	0.026 (2)
C14	0.0382 (17)	0.061 (2)	0.061 (2)	0.0172 (15)	0.0088 (15)	0.0187 (17)
C15	0.0266 (14)	0.0473 (17)	0.0510 (18)	0.0126 (12)	0.0080 (12)	0.0098 (14)
C16	0.0467 (19)	0.057 (2)	0.056 (2)	0.0135 (16)	0.0076 (15)	0.0082 (16)
C17	0.072 (3)	0.064 (3)	0.079 (3)	0.013 (2)	0.006 (2)	−0.011 (2)
C18	0.084 (3)	0.048 (2)	0.116 (4)	0.016 (2)	0.018 (3)	0.003 (3)
C19	0.070 (3)	0.058 (2)	0.101 (4)	0.027 (2)	0.019 (2)	0.035 (2)
C20	0.0318 (15)	0.0501 (17)	0.0403 (16)	0.0131 (13)	0.0038 (12)	0.0112 (13)
C21	0.0349 (15)	0.0503 (18)	0.0403 (16)	0.0104 (13)	0.0004 (12)	0.0083 (13)
C22	0.0440 (19)	0.061 (2)	0.063 (2)	0.0069 (16)	0.0094 (16)	−0.0031 (18)
C23	0.070 (3)	0.068 (3)	0.080 (3)	0.019 (2)	0.016 (2)	−0.015 (2)
C24	0.078 (3)	0.051 (2)	0.066 (2)	0.012 (2)	−0.006 (2)	−0.0013 (18)
C25	0.065 (2)	0.052 (2)	0.068 (2)	0.0018 (18)	0.0057 (19)	0.0139 (18)
C26	0.0496 (19)	0.055 (2)	0.062 (2)	0.0105 (16)	0.0150 (16)	0.0140 (17)
I1	0.0951 (2)	0.07203 (19)	0.05011 (16)	−0.00014 (15)	−0.01240 (14)	0.00788 (12)
I2	0.0750 (2)	0.1171 (3)	0.05523 (17)	0.02581 (17)	0.00003 (13)	0.02980 (16)
N1	0.0307 (12)	0.0415 (14)	0.0573 (16)	0.0094 (10)	0.0078 (11)	0.0137 (12)
N2	0.0334 (14)	0.0629 (18)	0.079 (2)	0.0186 (13)	0.0168 (13)	0.0303 (16)
N3	0.0281 (12)	0.0465 (15)	0.0505 (15)	0.0117 (11)	0.0052 (11)	0.0094 (12)
N4	0.0317 (14)	0.0513 (16)	0.084 (2)	0.0090 (12)	0.0151 (14)	0.0037 (15)

Geometric parameters (Å, º) top

C1—C6	1.386 (5)	C14—I2	2.098 (4)
C1—C2	1.396 (5)	C15—C16	1.400 (5)
C1—I1	2.094 (3)	C15—N3	1.415 (4)
C2—C3	1.392 (5)	C16—C17	1.382 (5)
C2—N1	1.417 (4)	C16—H16	0.9300
C3—C4	1.376 (5)	C17—C18	1.373 (7)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.383 (6)	C18—C19	1.378 (7)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.368 (6)	C19—H19	0.9300
C5—H5	0.9300	C20—N3	1.293 (4)
C6—H6	0.9300	C20—N4	1.352 (4)
C7—N1	1.294 (4)	C20—C21	1.485 (4)
C7—N2	1.349 (4)	C21—C22	1.387 (5)
C7—C8	1.496 (4)	C21—C26	1.388 (5)
C8—C13	1.387 (5)	C22—C23	1.381 (6)
C8—C9	1.386 (4)	C22—H22	0.9300
C9—C10	1.381 (5)	C23—C24	1.378 (6)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.377 (5)	C24—C25	1.360 (6)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.367 (6)	C25—C26	1.384 (5)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.389 (5)	C26—H26	0.9300
C12—H12	0.9300	N2—H2A	0.8600
C13—H13	0.9300	N2—H2B	0.8600
C14—C19	1.382 (6)	N4—H4A	0.8600
C14—C15	1.401 (5)	N4—H4B	0.8600

C6—C1—C2	121.2 (3)	C16—C15—N3	120.5 (3)
C6—C1—I1	118.7 (3)	C14—C15—N3	121.4 (3)
C2—C1—I1	120.1 (2)	C17—C16—C15	120.9 (4)
C3—C2—C1	117.4 (3)	C17—C16—H16	119.5
C3—C2—N1	120.7 (3)	C15—C16—H16	119.5
C1—C2—N1	121.7 (3)	C18—C17—C16	119.8 (4)
C4—C3—C2	121.2 (3)	C18—C17—H17	120.1
C4—C3—H3	119.4	C16—C17—H17	120.1
C2—C3—H3	119.4	C17—C18—C19	120.6 (4)
C3—C4—C5	120.4 (4)	C17—C18—H18	119.7
C3—C4—H4	119.8	C19—C18—H18	119.7
C5—C4—H4	119.8	C18—C19—C14	120.0 (4)
C6—C5—C4	119.6 (4)	C18—C19—H19	120.0
C6—C5—H5	120.2	C14—C19—H19	120.0
C4—C5—H5	120.2	N3—C20—N4	123.5 (3)
C5—C6—C1	120.2 (4)	N3—C20—C21	118.8 (3)
C5—C6—H6	119.9	N4—C20—C21	117.7 (3)
C1—C6—H6	119.9	C22—C21—C26	118.2 (3)
N1—C7—N2	123.9 (3)	C22—C21—C20	119.5 (3)
N1—C7—C8	118.7 (3)	C26—C21—C20	122.2 (3)
N2—C7—C8	117.4 (3)	C23—C22—C21	120.4 (4)
C13—C8—C9	118.1 (3)	C23—C22—H22	119.8
C13—C8—C7	121.9 (3)	C21—C22—H22	119.8
C9—C8—C7	120.0 (3)	C24—C23—C22	120.6 (4)
C10—C9—C8	120.7 (3)	C24—C23—H23	119.7
C10—C9—H9	119.7	C22—C23—H23	119.7
C8—C9—H9	119.7	C25—C24—C23	119.6 (4)
C11—C10—C9	120.7 (3)	C25—C24—H24	120.2
C11—C10—H10	119.6	C23—C24—H24	120.2
C9—C10—H10	119.6	C24—C25—C26	120.4 (4)
C12—C11—C10	119.2 (4)	C24—C25—H25	119.8
C12—C11—H11	120.4	C26—C25—H25	119.8
C10—C11—H11	120.4	C25—C26—C21	120.8 (3)
C11—C12—C13	120.5 (4)	C25—C26—H26	119.6
C11—C12—H12	119.8	C21—C26—H26	119.6
C13—C12—H12	119.8	C7—N1—C2	118.8 (2)
C8—C13—C12	120.8 (3)	C7—N2—H2A	120.0
C8—C13—H13	119.6	C7—N2—H2B	120.0
C12—C13—H13	119.6	H2A—N2—H2B	120.0
C19—C14—C15	120.7 (4)	C20—N3—C15	117.9 (2)
C19—C14—I2	119.9 (3)	C20—N4—H4A	120.0
C15—C14—I2	119.4 (3)	C20—N4—H4B	120.0
C16—C15—C14	118.0 (3)	H4A—N4—H4B	120.0

C6—C1—C2—C3	1.1 (5)	C14—C15—C16—C17	1.0 (5)
I1—C1—C2—C3	179.8 (2)	N3—C15—C16—C17	175.5 (3)
C6—C1—C2—N1	−172.8 (3)	C15—C16—C17—C18	−0.7 (6)
I1—C1—C2—N1	5.9 (4)	C16—C17—C18—C19	0.2 (7)
C1—C2—C3—C4	0.1 (5)	C17—C18—C19—C14	0.1 (7)
N1—C2—C3—C4	174.0 (3)	C15—C14—C19—C18	0.2 (6)
C2—C3—C4—C5	−0.9 (6)	I2—C14—C19—C18	−179.0 (3)
C3—C4—C5—C6	0.5 (7)	N3—C20—C21—C22	−22.0 (4)
C4—C5—C6—C1	0.7 (7)	N4—C20—C21—C22	158.7 (3)
C2—C1—C6—C5	−1.5 (6)	N3—C20—C21—C26	159.4 (3)
I1—C1—C6—C5	179.8 (3)	N4—C20—C21—C26	−20.0 (5)
N1—C7—C8—C13	160.1 (3)	C26—C21—C22—C23	−1.0 (5)
N2—C7—C8—C13	−19.0 (5)	C20—C21—C22—C23	−179.7 (4)
N1—C7—C8—C9	−19.3 (4)	C21—C22—C23—C24	1.2 (7)
N2—C7—C8—C9	161.7 (3)	C22—C23—C24—C25	−0.2 (7)
C13—C8—C9—C10	0.2 (5)	C23—C24—C25—C26	−1.0 (6)
C7—C8—C9—C10	179.6 (3)	C24—C25—C26—C21	1.3 (6)
C8—C9—C10—C11	0.6 (6)	C22—C21—C26—C25	−0.2 (5)
C9—C10—C11—C12	−0.8 (6)	C20—C21—C26—C25	178.4 (3)
C10—C11—C12—C13	0.0 (7)	N2—C7—N1—C2	−2.4 (5)
C9—C8—C13—C12	−1.0 (6)	C8—C7—N1—C2	178.6 (3)
C7—C8—C13—C12	179.7 (4)	C3—C2—N1—C7	96.8 (4)
C11—C12—C13—C8	0.9 (7)	C1—C2—N1—C7	−89.5 (4)
C19—C14—C15—C16	−0.7 (5)	N4—C20—N3—C15	−6.6 (5)
I2—C14—C15—C16	178.6 (2)	C21—C20—N3—C15	174.1 (3)
C19—C14—C15—N3	−175.2 (3)	C16—C15—N3—C20	101.4 (3)
I2—C14—C15—N3	4.0 (4)	C14—C15—N3—C20	−84.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N3ⁱ	0.86	2.25	3.057 (4)	156
N4—H4B···N1ⁱⁱ	0.86	2.24	3.027 (4)	151

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁IN₂
M_r	322.14
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.411 (3), 11.024 (3), 11.534 (3)
α, β, γ (°)	95.501 (3), 95.065 (3), 102.986 (3)
V (Å³)	1275.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.49
Crystal size (mm)	0.49 × 0.44 × 0.30

Data collection
Diffractometer	CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.376, 0.523
No. of measured, independent and observed [I > 2σ(I)] reflections	9707, 4716, 4076
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.079, 1.04
No. of reflections	4716
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.94, −1.34

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N3ⁱ	0.86	2.25	3.057 (4)	156.0
N4—H4B···N1ⁱⁱ	0.86	2.24	3.027 (4)	151.3

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

Acknowledgements

The authors are grateful for the financial support of the Science and Technology Department of Zhejiang Province Foundation of China (project No. 2010 C32022) and the Zhejiang Province Natural Science Foundation of China (project No. Y4090410).

References

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