(E)-1-(2-Iodo-phen-yl)-2-phenyl-diazene.

The mol-ecule of the title compound, C(12)H(9)IN(2), is approximately planar [maximum deviation = 0.020 (5) Å] with a trans arrangement of the groups around the N=N double bond. This double bond is rotated away from the iodine substiuent.

Related literature

For the synthesis, see: Badger et al. (1964 ▶).

Experimental

Crystal data

C12H9IN2

M = 308.11

Orthorhombic,

a = 4.628 (3) Å

b = 12.801 (9) Å

c = 18.312 (12) Å

V = 1084.9 (13) Å3

Z = 4

Mo Kα radiation

μ = 2.92 mm−1

T = 296 K

1.00 × 0.07 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.783, T max = 0.822

10050 measured reflections

1930 independent reflections

1842 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.070

S = 1.07

1930 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.48 e Å−3

Absolute structure: Flack (1983 ▶), 763 Friedel pairs

Flack parameter: 0.08 (4)

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) in WinGX (Farrugia, 1999 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811032119/qm2021sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032119/qm2021Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032119/qm2021Isup3.cml

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

C12H9IN2	F(000) = 592
Mr = 308.11	Dx = 1.886 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4258 reflections
a = 4.628 (3) Å	θ = 2.2–25.0°
b = 12.801 (9) Å	µ = 2.92 mm−1
c = 18.312 (12) Å	T = 296 K
V = 1084.9 (13) Å3	Needle, orange
Z = 4	1.00 × 0.07 × 0.07 mm

Bruker APEXII CCD diffractometer	1930 independent reflections
Radiation source: sealed tube	1842 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −5→5
Tmin = 0.783, Tmax = 0.822	k = −15→15
10050 measured reflections	l = −21→21

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H-atom parameters constrained
wR(F2) = 0.070	w = 1/[σ2(Fo2) + (0.0345P)2 + 0.6387P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
1930 reflections	Δρmax = 0.57 e Å−3
137 parameters	Δρmin = −0.48 e Å−3
0 restraints	Absolute structure: Flack (1983), 763 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (4)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.1092 (10)	0.3166 (4)	0.1768 (3)	0.0549 (12)
H1	−0.0297	0.3672	0.1865	0.066*
C2	0.1881 (10)	0.2473 (3)	0.2300 (3)	0.0521 (11)
H2	0.1032	0.2496	0.2760	0.062*
C3	0.3968 (9)	0.1737 (3)	0.2138 (2)	0.0450 (10)
C4	0.5235 (10)	0.1691 (3)	0.1465 (2)	0.0389 (8)
C5	1.0496 (8)	0.0040 (3)	0.0680 (2)	0.0407 (9)
C6	1.1155 (10)	−0.0629 (3)	0.1240 (3)	0.0530 (10)
H6	1.0261	−0.0561	0.1693	0.064*
C7	1.3160 (11)	−0.1401 (4)	0.1121 (3)	0.0643 (13)
H7	1.3637	−0.1860	0.1495	0.077*
C8	1.4446 (10)	−0.1497 (4)	0.0459 (3)	0.0637 (14)
H8	1.5794	−0.2025	0.0383	0.076*
C9	0.2346 (10)	0.3116 (3)	0.1090 (3)	0.0523 (11)
H9	0.1763	0.3584	0.0731	0.063*
C10	0.4372 (8)	0.2417 (3)	0.0934 (2)	0.0420 (10)
H10	0.5218	0.2408	0.0473	0.050*
C11	1.1796 (10)	−0.0058 (4)	0.0017 (3)	0.0550 (12)
H11	1.1331	0.0400	−0.0360	0.066*
C12	1.3793 (10)	−0.0833 (4)	−0.0095 (3)	0.0638 (14)
H12	1.4693	−0.0903	−0.0546	0.077*
N1	0.8420 (7)	0.0855 (3)	0.07490 (19)	0.0433 (8)
N2	0.7314 (7)	0.0892 (3)	0.13658 (19)	0.0422 (8)
I1	0.51175 (8)	0.06841 (2)	0.294862 (15)	0.06222 (13)

	U11	U22	U33	U12	U13	U23
C1	0.050 (2)	0.039 (2)	0.075 (3)	0.0054 (19)	0.000 (2)	−0.010 (2)
C2	0.048 (3)	0.052 (3)	0.056 (3)	−0.006 (2)	0.009 (2)	−0.013 (2)
C3	0.045 (2)	0.042 (2)	0.048 (2)	−0.0057 (17)	−0.0028 (18)	−0.0042 (18)
C4	0.036 (2)	0.0332 (16)	0.0476 (19)	0.003 (2)	0.000 (2)	−0.0029 (13)
C5	0.032 (2)	0.039 (2)	0.051 (2)	0.0013 (18)	−0.0029 (18)	−0.0058 (15)
C6	0.051 (2)	0.050 (2)	0.058 (3)	0.005 (2)	0.001 (2)	0.002 (2)
C7	0.056 (3)	0.051 (3)	0.086 (4)	0.011 (2)	−0.006 (3)	0.006 (3)
C8	0.043 (3)	0.048 (2)	0.100 (4)	0.008 (2)	−0.007 (3)	−0.021 (2)
C9	0.055 (3)	0.042 (2)	0.060 (3)	−0.002 (2)	−0.013 (2)	0.003 (2)
C10	0.038 (2)	0.047 (2)	0.041 (2)	−0.0067 (18)	−0.0007 (17)	−0.0027 (16)
C11	0.054 (3)	0.063 (3)	0.049 (3)	0.004 (2)	−0.001 (2)	−0.005 (2)
C12	0.046 (2)	0.079 (4)	0.066 (3)	0.005 (3)	0.003 (2)	−0.025 (3)
N1	0.0426 (18)	0.040 (2)	0.047 (2)	0.0022 (16)	0.0011 (16)	−0.0016 (15)
N2	0.0394 (17)	0.044 (2)	0.0433 (19)	−0.0003 (15)	0.0006 (15)	−0.0031 (15)
I1	0.0674 (2)	0.0688 (2)	0.05044 (18)	−0.0007 (2)	0.0006 (2)	0.01231 (12)

C1—C2	1.367 (7)	C6—H6	0.9300
C1—C9	1.371 (7)	C7—C8	1.356 (7)
C1—H1	0.9300	C7—H7	0.9300
C2—C3	1.381 (6)	C8—C12	1.357 (7)
C2—H2	0.9300	C8—H8	0.9300
C3—C4	1.367 (6)	C9—C10	1.328 (6)
C3—I1	2.075 (4)	C9—H9	0.9300
C4—C10	1.403 (5)	C10—H10	0.9300
C4—N2	1.416 (5)	C11—C12	1.371 (7)
C5—C11	1.361 (6)	C11—H11	0.9300
C5—C6	1.370 (6)	C12—H12	0.9300
C5—N1	1.424 (5)	N1—N2	1.241 (5)
C6—C7	1.374 (6)
C2—C1—C9	120.1 (4)	C8—C7—H7	119.9
C2—C1—H1	120.0	C6—C7—H7	119.9
C9—C1—H1	120.0	C7—C8—C12	120.9 (4)
C1—C2—C3	118.5 (4)	C7—C8—H8	119.5
C1—C2—H2	120.8	C12—C8—H8	119.5
C3—C2—H2	120.8	C10—C9—C1	121.7 (4)
C4—C3—C2	121.5 (4)	C10—C9—H9	119.1
C4—C3—I1	120.5 (3)	C1—C9—H9	119.1
C2—C3—I1	118.0 (3)	C9—C10—C4	119.9 (4)
C3—C4—C10	118.3 (4)	C9—C10—H10	120.1
C3—C4—N2	116.0 (3)	C4—C10—H10	120.1
C10—C4—N2	125.7 (4)	C5—C11—C12	119.8 (5)
C11—C5—C6	120.8 (4)	C5—C11—H11	120.1
C11—C5—N1	116.4 (4)	C12—C11—H11	120.1
C6—C5—N1	122.8 (4)	C8—C12—C11	119.5 (5)
C5—C6—C7	118.7 (5)	C8—C12—H12	120.3
C5—C6—H6	120.6	C11—C12—H12	120.3
C7—C6—H6	120.6	N2—N1—C5	112.8 (3)
C8—C7—C6	120.3 (5)	N1—N2—C4	115.1 (3)
C9—C1—C2—C3	0.6 (7)	C1—C9—C10—C4	1.3 (7)
C1—C2—C3—C4	−0.1 (6)	C3—C4—C10—C9	−0.8 (6)
C1—C2—C3—I1	−179.5 (3)	N2—C4—C10—C9	178.5 (4)
C2—C3—C4—C10	0.3 (6)	C6—C5—C11—C12	−0.1 (7)
I1—C3—C4—C10	179.6 (3)	N1—C5—C11—C12	−179.2 (4)
C2—C3—C4—N2	−179.1 (4)	C7—C8—C12—C11	−0.3 (8)
I1—C3—C4—N2	0.2 (5)	C5—C11—C12—C8	0.1 (7)
C11—C5—C6—C7	0.1 (7)	C11—C5—N1—N2	179.6 (4)
N1—C5—C6—C7	179.1 (4)	C6—C5—N1—N2	0.5 (5)
C5—C6—C7—C8	−0.2 (7)	C5—N1—N2—C4	179.9 (3)
C6—C7—C8—C12	0.3 (8)	C3—C4—N2—N1	179.3 (4)
C2—C1—C9—C10	−1.2 (7)	C10—C4—N2—N1	0.0 (6)