(E)-1-(2-Iodo­phen­yl)-2-phenyl­diazene

Wragg, D.S.; Ahmed, M.A.K.; Nilsen, O.; Fjellvåg, H.

doi:10.1107/S1600536811032119

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2326

doi:10.1107/S1600536811032119

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(E)-1-(2-Iodophenyl)-2-phenyldiazene

David S. Wragg,^a ^* Mohammed A. K. Ahmed,^b Ola Nilsen ^b and Helmer Fjellvåg ^b

^ainGAP Centre for Research Based Innovation, Center for Materials Science and Nanotechnology, Department of Chemistry, University of Oslo, PO Box 1033 Blindern, Oslo 0315, Norway, and ^bDepartment of Chemistry, University of Oslo, PO Box 1033 Blindern, Oslo 0315, Norway
^*Correspondence e-mail: david.wragg@smn.uio.no

(Received 3 August 2011; accepted 8 August 2011; online 11 August 2011)

The molecule of the title compound, C₁₂H₉IN₂, 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_r = 308.11
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.070
S = 1.07
1930 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811032119/qm2021sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811032119/qm2021Isup3.cml

checkCIF report

Comment top

(E)-1-(2-iodophenyl)-2-phenyldiazene (1) was synthesized by a literature procedure (Badger et al. 1964) and recrystallized from absolute ethanol. The molecule is planar with a trans arrangement of the phenyl groups around the N—N double bond. This double bond is rotated away from the iodine substiuent on C3 (Fig. 1). There are no strong intermolecular interactions, although π-stacking interactions may exist between the phenyl rings and the N—N double bonds (Fig. 2, 3).

Related literature top

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

Experimental top

(1) was synthesized according to the literature procedure (Badger et al. 1964) and recrystallized from absolute ethanol in the form of long orange needles.

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); 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).

Figures top

	Fig. 1. The asymmetric unit of (1) shown with thermal ellipsoids at 50% probability. Hydrogen atoms unlabelled for clarity.
	Fig. 2. Packing diagram of (1) viewed along the a-axis.
	Fig. 3. Packing diagram of (1) viewed along the c-axis.

(E)-1-(2-Iodophenyl)-2-phenyldiazene top

Crystal data top

C₁₂H₉IN₂	F(000) = 592
M_r = 308.11	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	1930 independent reflections
Radiation source: sealed tube	1842 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −5→5
T_min = 0.783, T_max = 0.822	k = −15→15
10050 measured reflections	l = −21→21

Refinement top

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(F_o²) + (0.0345P)² + 0.6387P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
1930 reflections	Δρ_max = 0.57 e Å⁻³
137 parameters	Δρ_min = −0.48 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 763 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (4)

Crystal data top

C₁₂H₉IN₂	V = 1084.9 (13) Å³
M_r = 308.11	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.628 (3) Å	µ = 2.92 mm⁻¹
b = 12.801 (9) Å	T = 296 K
c = 18.312 (12) Å	1.00 × 0.07 × 0.07 mm

Data collection top

Bruker APEXII CCD diffractometer	1930 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2011)	1842 reflections with I > 2σ(I)
T_min = 0.783, T_max = 0.822	R_int = 0.033
10050 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.070	Δρ_max = 0.57 e Å⁻³
S = 1.07	Δρ_min = −0.48 e Å⁻³
1930 reflections	Absolute structure: Flack (1983), 763 Friedel pairs
137 parameters	Absolute structure parameter: 0.08 (4)
0 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₂H₉IN₂
M_r	308.11
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	4.628 (3), 12.801 (9), 18.312 (12)
V (Å³)	1084.9 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.92
Crystal size (mm)	1.00 × 0.07 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2011)
T_min, T_max	0.783, 0.822
No. of measured, independent and observed [I > 2σ(I)] reflections	10050, 1930, 1842
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.070, 1.07
No. of reflections	1930
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.48
Absolute structure	Flack (1983), 763 Friedel pairs
Absolute structure parameter	0.08 (4)

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) in WinGX (Farrugia, 1999), DIAMOND (Brandenburg, 2006), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Acknowledgements

The Norwegian research council is acknowledged for funding under RENERGI project No. 200014.

References

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