N-(2-Iodo-phen-yl)benzene-carbox-imid-amide.

The title compound, C(13)H(11)IN(2), 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 = 322.14

Triclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.079

S = 1.04

4716 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −1.34 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681200596X/im2355sup1.cif

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

Supplementary material file. DOI: 10.1107/S160053681200596X/im2355Isup3.cml

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

C13H11IN2	Z = 4
Mr = 322.14	F(000) = 624
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0273P)2 + 1.8412P] where P = (Fo2 + 2Fc2)/3
4716 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −1.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .