N,N′-Bis(4-iodo­phenyl)­diazene N-oxide

Krivokapić, A.; Wilson, C.J.; Watkin, D.J.; Anderson, H.L.

doi:10.1107/S1600536803013618

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N,N'-Bis(4-iodophenyl)diazene N-oxide

A. Krivokapic, C. J. Wilson, D. J. Watkin and H. L. Anderson

The title compound, C₁₂H₈I₂N₂O, was obtained as an unexpected product while attempting to protect N,N-dibutyl-4-iodoaniline as the N-oxide. It crystallizes as a layer structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013618/dn6079sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013618/dn6079Isup2.hkl Contains datablock I

CCDC reference: 217605

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (Please check) = 0.000 Å
R factor = 0.055
wR factor = 0.105
Data-to-parameter ratio = 9.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



STRVAL_01
         From the CIF: _refine_ls_abs_structure_Flack    0.460
         From the CIF: _refine_ls_abs_structure_Flack_su    0.090
           Alert C Flack test results are ambiguous.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.49
         From the CIF: _reflns_number_total               2682
         Count of symmetry unique reflns         1612
         Completeness (_total/calc)            166.38%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1070
         Fraction of Friedel pairs measured     0.664
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

The title compound, (I), was obtained in 10% yield as an unexpected product while attempting to convert N,N-dibutyl-4-iodoaniline into its N-oxide with hydrogen peroxide (Demir & Ashaw, 1987), and identified crystallographically. To the best of our knowledge, the direct transformation of a tertiary amine into a diazo compound is unprecedented. Compound (I) has previously been prepared by several routes (e.g. Gabriel, 1876; Wang et al., 1999); the melting point, NMR data and mass spectrum of our product confirmed its identity. A possible mechanism for the formation of this compound is shown in the Scheme below.

Oxidation of (II) by hydrogen peroxide gives the N-oxide (III). This eliminates butene via a Cope reaction (Adams & Kovacic, 1974) before being oxidized again [to give (IV)] and undergoing a second elimination [to give (V)]. Di(hydroxyl)amine (V) then eliminates water to give nitrosamine (VI). From this point, it is likely that the mechanism is similar to that of the reaction between nitrosobenzene and phenylhydroxylamine (Becker & Sternson, 1980) (a radical mechanism is also seen in the presence of base (Russell et al., 1967). Nucleophilic attack by the species that has undergone one elimination (VII) forms dimer (VIII). This undergoes a further elimination (to give IX), followed by displacement of OH⁻ by the lone pair of the adjacent N atom to give (I). (I) crystallizes as an inversion twin [Flack (Flack & Bernardinelli, 1999, 2000) parameter = 0.46 (9)]. The whole molecule is also disordered with an image of itself in the ratio 4:1. The image can be regarded as being due either to a local pseudo-centre of symmery, or a stacking fault with translation of approximately 1/4 along z. This is the preferred description since the structure consists of layers of molecules perpendicular to z, with a layer thickness of z/4. The minimum I···I distances between layers is 4.05 Å. The bond lengths and angles are comparable to similar azoxy compounds. Short intramolecular contacts occur between O1 and H41 (2.04 Å), and between O1 and H101 (2.31 Å), both of these are shorter than the sum of the van der Waals radii (2.68 Å; Rowland & Taylor, 1996).

Experimental top

A mixture of N,N-dibutyl-4-iodoaniline (1.3 g, 3.93 mmol), chloroform (2.5 ml), methanol (2.5 ml) and hydrogen peroxide (35% w/w in water, 2.5 ml) was heated to reflux. Starting material was still present after 24 h, as shown by thin-layer chromatography (silica), 9:1 60–80 petroleum ether–DCM, R_F = 0.78). Further additions of hydrogen peroxide (35% w/w in water, 2.5 ml) were made every 24 h for 4 d until the starting material had been consumed. The product was then isolated by extraction into chloroform followed by crystallization (DCM/60–80 petroleum ether) to give colourless crystals (180 mg, 10%). M.p. 471 K. Crystals were grown by slow evaporation of a solution in CDCl₃. (λ_max (CH₂Cl₂)/nm log (ε): 239 (4.08), 343 (4.13) m/z (TOF MS ES⁺): 454.54 ([M + 4H]⁺), 330.07 ([M - I + 4H]⁺, 100%), 327.17 ([M - I + H]⁺), 217.01 ([M - IC₆H₄NO]⁺), 201.07 ([M - I + 3H]⁺).

Computing details top

Data collection: COLLECT (Nonius BV, 1997–2001); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1996); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 2001); molecular graphics: CAMERON; software used to prepare material for publication: CRYSTALS.

Figures top

	Fig. 1. Plot showing the atomic numbering scheme for (I). Displacement ellipsoids are drawn at the 50% probability level for non-H atoms.
	Fig. 2. The unit cell of (I), viewed normal to the b axis, showing all N—O groups pointing in the same direction.

(I) top

Crystal data top

C₁₂H₈I₂N₂O	D_x = 2.337 Mg m⁻³
M_r = 450.02	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, I2cb	Cell parameters from 1542 reflections
a = 6.0119 (1) Å	θ = 1–27°
b = 7.2082 (2) Å	µ = 4.90 mm⁻¹
c = 59.0233 (18) Å	T = 150 K
V = 2557.77 (11) Å³	Plate, white
Z = 8	0.20 × 0.19 × 0.01 mm
F(000) = 1663.999

Data collection top

Nonius KappaCCD diffractometer	2681 reflections with I > −10.00u(I)
Graphite monochromator	R_int = 0.00
ω scans	θ_max = 27.5°, θ_min = 1.4°
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1996)	h = −7→7
T_min = 0.39, T_max = 0.95	k = −9→9
2815 measured reflections	l = −74→75
2682 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters not refined
R[F² > 2σ(F²)] = 0.055	W = q/[σ²⁽^F^{) + [}^P^(1)p]2 + P(2)p + P(4) + P(5)Sinθ]
wR(F²) = 0.105	(Δ/σ)_max = 0.003
S = 0.98	Δρ_max = 1.78 e Å⁻³
2681 reflections	Δρ_min = −1.70 e Å⁻³
296 parameters	Absolute structure: Flack & Bernadinelli (1999, 2000), 1226 Friedel-pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.46 (9)

Crystal data top

C₁₂H₈I₂N₂O	V = 2557.77 (11) Å³
M_r = 450.02	Z = 8
Orthorhombic, I2cb	Mo Kα radiation
a = 6.0119 (1) Å	µ = 4.90 mm⁻¹
b = 7.2082 (2) Å	T = 150 K
c = 59.0233 (18) Å	0.20 × 0.19 × 0.01 mm

Data collection top

Nonius KappaCCD diffractometer	2682 independent reflections
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1996)	2681 reflections with I > −10.00u(I)
T_min = 0.39, T_max = 0.95	R_int = 0.00
2815 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	H-atom parameters not refined
wR(F²) = 0.105	Δρ_max = 1.78 e Å⁻³
S = 0.98	Δρ_min = −1.70 e Å⁻³
2681 reflections	Absolute structure: Flack & Bernadinelli (1999, 2000), 1226 Friedel-pairs
296 parameters	Absolute structure parameter: 0.46 (9)

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.7945 (13)	0.2264 (4)	0.52342 (8)	0.0512	0.802 (8)
I2	−0.129 (1)	0.2883 (2)	0.72751 (4)	0.0371	0.802 (8)
C1	0.6587 (16)	0.2379 (9)	0.55608 (12)	0.0312	0.802 (8)
C2	0.7826 (16)	0.1710 (9)	0.57436 (14)	0.0348	0.802 (8)
C3	0.6882 (14)	0.1798 (8)	0.59614 (12)	0.0348	0.802 (8)
C4	0.4740 (12)	0.2548 (8)	0.59870 (9)	0.0280	0.802 (8)
C5	0.3592 (14)	0.3208 (8)	0.58020 (12)	0.0324	0.802 (8)
C6	0.4471 (16)	0.3125 (9)	0.55870 (13)	0.0368	0.802 (8)
C7	0.0589 (16)	0.2680 (8)	0.69762 (12)	0.0291	0.802 (8)
C8	0.2717 (16)	0.1925 (9)	0.69799 (14)	0.0355	0.802 (8)
C9	0.3930 (15)	0.1755 (9)	0.67824 (13)	0.0391	0.802 (8)
C10	0.3040 (11)	0.2337 (7)	0.65805 (9)	0.0331	0.802 (8)
C11	0.0894 (14)	0.3111 (8)	0.65727 (12)	0.0352	0.802 (8)
C12	−0.0342 (16)	0.3277 (9)	0.67726 (14)	0.0304	0.802 (8)
N1	0.3773 (16)	0.2668 (8)	0.62055 (11)	0.0344	0.802 (8)
N2	0.4321 (12)	0.2134 (9)	0.63721 (12)	0.0364	0.802 (8)
O1	0.6288 (13)	0.1353 (9)	0.64031 (12)	0.0506	0.802 (8)
I201	0.826 (3)	0.2238 (17)	0.5215 (4)	0.0512	0.198 (8)
I202	−0.0814 (19)	0.280 (1)	0.72716 (19)	0.0371	0.198 (8)
O201	0.096 (3)	0.3700 (17)	0.6112 (5)	0.0419	0.198 (8)
N201	0.296 (3)	0.2953 (17)	0.6130 (3)	0.0391	0.198 (8)
N202	0.344 (4)	0.255 (2)	0.6301 (3)	0.0402	0.198 (8)
C201	0.650 (5)	0.248 (2)	0.5519 (4)	0.0333	0.198 (8)
C202	0.749 (4)	0.187 (2)	0.5719 (5)	0.0342	0.198 (8)
C203	0.630 (3)	0.2030 (14)	0.5921 (4)	0.0342	0.198 (8)
C204	0.418 (3)	0.2796 (13)	0.5921 (3)	0.0336	0.198 (8)
C205	0.322 (4)	0.3405 (16)	0.5720 (3)	0.0372	0.198 (8)
C206	0.438 (5)	0.325 (2)	0.5517 (3)	0.0370	0.198 (8)
C207	0.059 (3)	0.2724 (15)	0.6949 (3)	0.0292	0.198 (8)
C208	0.271 (3)	0.1994 (15)	0.6922 (3)	0.0336	0.198 (8)
C209	0.364 (3)	0.1938 (15)	0.6707 (3)	0.0327	0.198 (8)
C210	0.246 (3)	0.2607 (15)	0.6522 (3)	0.0364	0.198 (8)
C211	0.032 (3)	0.3341 (15)	0.6550 (3)	0.0327	0.198 (8)
C212	−0.063 (4)	0.3400 (16)	0.6766 (4)	0.0307	0.198 (8)
H101	0.5458	0.1208	0.6786	0.0469*	0.802 (8)
H102	0.3375	0.1503	0.7127	0.0426*	0.802 (8)
H104	−0.1874	0.3817	0.6769	0.0365*	0.802 (8)
H105	0.0256	0.3540	0.6425	0.0422*	0.802 (8)
H2101	0.5164	0.1415	0.6685	0.0392*	0.198 (8)
H2102	0.3554	0.1515	0.7056	0.0403*	0.198 (8)
H2104	−0.2152	0.3920	0.6788	0.0368*	0.198 (8)
H2105	−0.0519	0.3820	0.6416	0.0393*	0.198 (8)
H2041	0.6983	0.1597	0.6066	0.0411*	0.198 (8)
H2042	0.9016	0.1318	0.5717	0.0411*	0.198 (8)
H2044	0.3697	0.3686	0.5371	0.0444*	0.198 (8)
H2045	0.1692	0.3955	0.5721	0.0446*	0.198 (8)
H41	0.7724	0.1334	0.6096	0.0418*	0.802 (8)
H42	0.9347	0.1182	0.5720	0.0418*	0.802 (8)
H44	0.3612	0.3588	0.5453	0.0442*	0.802 (8)
H45	0.2083	0.3761	0.5824	0.0389*	0.802 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0700 (16)	0.0544 (4)	0.029 (1)	−0.0077 (7)	0.0141 (7)	−0.0057 (3)
I2	0.0341 (12)	0.0453 (3)	0.0320 (3)	−0.0011 (5)	0.0050 (6)	−0.0012 (3)
C1	0.042 (4)	0.030 (4)	0.021 (4)	−0.001 (3)	−0.007 (4)	0.004 (3)
C2	0.035 (4)	0.028 (4)	0.041 (4)	0.009 (4)	−0.006 (4)	0.000 (3)
C3	0.043 (5)	0.028 (4)	0.034 (4)	0.007 (4)	−0.010 (4)	0.008 (3)
C4	0.034 (4)	0.025 (4)	0.025 (4)	−0.002 (3)	0.006 (3)	0.007 (3)
C5	0.030 (4)	0.034 (4)	0.034 (4)	0.008 (4)	−0.004 (4)	0.006 (3)
C6	0.041 (4)	0.040 (5)	0.030 (5)	0.001 (4)	−0.003 (4)	0.015 (4)
C7	0.031 (4)	0.029 (4)	0.027 (4)	−0.001 (3)	0.006 (3)	0.000 (3)
C8	0.030 (4)	0.035 (4)	0.042 (5)	0.004 (4)	0.010 (4)	0.009 (3)
C9	0.043 (5)	0.029 (4)	0.045 (4)	0.002 (4)	0.006 (4)	0.011 (4)
C10	0.034 (4)	0.028 (4)	0.037 (4)	−0.001 (3)	0.004 (3)	−0.000 (3)
C11	0.046 (5)	0.027 (4)	0.033 (4)	0.001 (4)	−0.003 (4)	0.006 (4)
C12	0.027 (4)	0.024 (4)	0.040 (4)	0.005 (3)	−0.002 (3)	−0.001 (3)
N1	0.037 (4)	0.038 (4)	0.028 (3)	−0.011 (4)	0.011 (3)	−0.008 (3)
N2	0.038 (4)	0.033 (3)	0.038 (3)	0.005 (3)	0.008 (3)	−0.001 (3)
O1	0.048 (4)	0.063 (5)	0.040 (4)	0.027 (4)	0.003 (3)	−0.001 (3)
I201	0.0700 (16)	0.0544 (4)	0.029 (1)	−0.0077 (7)	0.0141 (7)	−0.0057 (3)
I202	0.0341 (12)	0.0453 (3)	0.0320 (3)	−0.0011 (5)	0.0050 (6)	−0.0012 (3)
O201	0.050 (9)	0.04 (1)	0.032 (9)	0.008 (8)	0.007 (8)	−0.002 (8)
N201	0.046 (6)	0.037 (6)	0.034 (5)	0.004 (5)	0.012 (5)	0.001 (5)
N202	0.042 (6)	0.040 (6)	0.039 (6)	0.009 (5)	0.006 (5)	−0.007 (6)
C201	0.043 (7)	0.033 (7)	0.024 (6)	0.001 (6)	−0.010 (6)	0.003 (6)
C202	0.040 (7)	0.028 (7)	0.034 (6)	0.007 (6)	−0.008 (6)	0.003 (6)
C203	0.047 (7)	0.027 (7)	0.029 (7)	0.005 (7)	−0.011 (6)	0.015 (7)
C204	0.041 (6)	0.031 (6)	0.028 (6)	0.004 (5)	0.004 (5)	0.005 (6)
C205	0.041 (8)	0.035 (7)	0.036 (6)	0.007 (7)	−0.001 (6)	0.016 (7)
C206	0.043 (7)	0.038 (7)	0.030 (6)	0.002 (7)	−0.004 (7)	0.015 (7)
C207	0.031 (6)	0.027 (7)	0.029 (5)	−0.001 (6)	0.008 (6)	0.007 (6)
C208	0.031 (7)	0.029 (7)	0.041 (6)	0.001 (7)	0.015 (7)	0.014 (7)
C209	0.04 (1)	0.02 (1)	0.035 (8)	0.00 (1)	0.016 (8)	0.017 (9)
C210	0.039 (5)	0.029 (5)	0.041 (5)	0.003 (5)	0.006 (4)	0.006 (5)
C211	0.042 (7)	0.022 (7)	0.034 (7)	0.002 (6)	−0.002 (6)	0.002 (7)
C212	0.029 (6)	0.026 (7)	0.037 (6)	0.005 (6)	−0.001 (6)	0.003 (6)

Geometric parameters (Å, º) top

I1—C1	2.095 (6)	N201—N202	1.090 (9)
I2—C7	2.098 (6)	N201—C204	1.438 (9)
C1—C2	1.397 (7)	N202—C210	1.433 (9)
C1—C6	1.390 (8)	C201—C202	1.391 (9)
C2—C3	1.407 (8)	C201—C206	1.393 (9)
C2—H42	1.000	C202—C203	1.396 (9)
C3—C4	1.405 (7)	C202—H2042	1.000
C3—H41	1.000	C203—C204	1.393 (9)
C4—C5	1.377 (7)	C203—H2041	1.000
C4—N1	1.417 (6)	C204—C205	1.389 (9)
C5—C6	1.376 (7)	C205—C206	1.392 (9)
C5—H45	1.000	C205—H2045	1.000
C6—H44	1.000	C206—H2044	1.000
C7—C8	1.391 (8)	C207—C208	1.389 (9)
C7—C12	1.394 (8)	C207—C212	1.392 (9)
C8—C9	1.380 (8)	C208—C209	1.387 (9)
C8—H102	1.000	C208—H2102	1.000
C9—C10	1.372 (7)	C209—C210	1.387 (9)
C9—H101	1.000	C209—H2101	1.000
C10—C11	1.406 (7)	C210—C211	1.398 (9)
C10—N2	1.459 (7)	C211—C212	1.393 (9)
C11—C12	1.400 (7)	C211—H2105	1.000
C11—H105	1.000	C212—H2104	1.000
C12—H104	1.000	H101—H2101	0.642
N2—O1	1.322 (7)	H102—H2102	0.433
I201—C201	2.088 (9)	H104—H2104	0.213
I202—C207	2.083 (9)	H105—H2105	0.510
O201—N201	1.321 (9)

I1—C1—C2	119.3 (6)	O201—N201—C204	115.1 (17)
I1—C1—C6	118.3 (6)	N202—N201—C204	129.8 (18)
C2—C1—C6	122.4 (7)	N201—N202—C210	136.8 (19)
C1—C2—C3	118.4 (7)	I201—C201—C202	119 (2)
C1—C2—H42	120.803	I201—C201—C206	119 (2)
C3—C2—H42	120.803	C202—C201—C206	121.8 (13)
C2—C3—C4	119.0 (5)	C201—C202—C203	118.7 (12)
C2—C3—H41	120.488	C201—C202—H2042	120.639
C4—C3—H41	120.488	C203—C202—H2042	120.639
C3—C4—C5	120.49 (13)	C202—C203—C204	120.0 (8)
C3—C4—N1	119.81 (9)	C202—C203—H2041	119.986
C5—C4—N1	119.69 (9)	C204—C203—H2041	119.986
C4—C5—C6	121.6 (5)	N201—C204—C203	119.8 (1)
C4—C5—H45	119.197	N201—C204—C205	119.8 (1)
C6—C5—H45	119.197	C203—C204—C205	120.49 (14)
C1—C6—C5	118.1 (7)	C204—C205—C206	120.2 (8)
C1—C6—H44	120.954	C204—C205—H2045	119.900
C5—C6—H44	120.954	C206—C205—H2045	119.900
I2—C7—C8	120.6 (6)	C201—C206—C205	118.8 (12)
I2—C7—C12	119.2 (6)	C201—C206—H2044	120.614
C8—C7—C12	120.2 (7)	C205—C206—H2044	120.614
C7—C8—C9	120.5 (7)	I202—C207—C208	119.1 (11)
C7—C8—H102	119.748	I202—C207—C212	119.3 (11)
C9—C8—H102	119.748	C208—C207—C212	121.6 (13)
C8—C9—C10	120.0 (6)	C207—C208—C209	119.1 (12)
C8—C9—H101	119.985	C207—C208—H2102	120.459
C10—C9—H101	119.985	C209—C208—H2102	120.459
C9—C10—C11	120.50 (13)	C208—C209—C210	120.2 (8)
C9—C10—N2	119.73 (9)	C208—C209—H2101	119.911
C11—C10—N2	119.77 (9)	C210—C209—H2101	119.911
C10—C11—C12	119.6 (5)	N202—C210—C209	119.7 (1)
C10—C11—H105	120.216	N202—C210—C211	119.8 (1)
C12—C11—H105	120.216	C209—C210—C211	120.49 (14)
C7—C12—C11	119.2 (7)	C210—C211—C212	119.7 (8)
C7—C12—H104	120.420	C210—C211—H2105	120.132
C11—C12—H104	120.419	C212—C211—H2105	120.132
C4—N1—N2	131.7 (7)	C207—C212—C211	118.9 (12)
C10—N2—N1	123.9 (6)	C207—C212—H2104	120.545
C10—N2—O1	113.4 (5)	C211—C212—H2104	120.545
N1—N2—O1	122.5 (8)	C212—H104—H2104	150.465
O201—N201—N202	115 (3)	C211—H105—H2105	102.986

Experimental details

Crystal data
Chemical formula	C₁₂H₈I₂N₂O
M_r	450.02
Crystal system, space group	Orthorhombic, I2cb
Temperature (K)	150
a, b, c (Å)	6.0119 (1), 7.2082 (2), 59.0233 (18)
V (Å³)	2557.77 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.90
Crystal size (mm)	0.20 × 0.19 × 0.01

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1996)
T_min, T_max	0.39, 0.95
No. of measured, independent and observed [I > −10.00u(I)] reflections	2815, 2682, 2681
R_int	0.00
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.105, 0.98
No. of reflections	2681
No. of parameters	296
No. of restraints	?
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	1.78, −1.70
Absolute structure	Flack & Bernadinelli (1999, 2000), 1226 Friedel-pairs
Absolute structure parameter	0.46 (9)

Computer programs: COLLECT (Nonius BV, 1997–2001), DENZO and SCALEPACK (Otwinowski & Minor, 1996), SIR92 (Altomare et al., 1994), CRYSTALS (Watkin et al., 2001), CAMERON, CRYSTALS.

Selected geometric parameters (Å, º) top

I1—C1	2.095 (6)	I202—C207	2.083 (9)
I2—C7	2.098 (6)	O201—N201	1.321 (9)
C1—C2	1.397 (7)	N201—N202	1.090 (9)
C1—C6	1.390 (8)	N201—C204	1.438 (9)
C2—C3	1.407 (8)	N202—C210	1.433 (9)
C3—C4	1.405 (7)	C201—C202	1.391 (9)
C4—C5	1.377 (7)	C201—C206	1.393 (9)
C4—N1	1.417 (6)	C202—C203	1.396 (9)
C5—C6	1.376 (7)	C203—C204	1.393 (9)
C7—C8	1.391 (8)	C204—C205	1.389 (9)
C7—C12	1.394 (8)	C205—C206	1.392 (9)
C8—C9	1.380 (8)	C207—C208	1.389 (9)
C9—C10	1.372 (7)	C207—C212	1.392 (9)
C10—C11	1.406 (7)	C208—C209	1.387 (9)
C10—N2	1.459 (7)	C209—C210	1.387 (9)
C11—C12	1.400 (7)	C210—C211	1.398 (9)
N2—O1	1.322 (7)	C211—C212	1.393 (9)
I201—C201	2.088 (9)

I1—C1—C2	119.3 (6)	O201—N201—N202	115 (3)
I1—C1—C6	118.3 (6)	O201—N201—C204	115.1 (17)
C2—C1—C6	122.4 (7)	N202—N201—C204	129.8 (18)
C1—C2—C3	118.4 (7)	N201—N202—C210	136.8 (19)
C2—C3—C4	119.0 (5)	I201—C201—C202	119 (2)
C3—C4—C5	120.49 (13)	I201—C201—C206	119 (2)
C3—C4—N1	119.81 (9)	C202—C201—C206	121.8 (13)
C5—C4—N1	119.69 (9)	C201—C202—C203	118.7 (12)
C4—C5—C6	121.6 (5)	C202—C203—C204	120.0 (8)
C1—C6—C5	118.1 (7)	N201—C204—C203	119.8 (1)
I2—C7—C8	120.6 (6)	N201—C204—C205	119.8 (1)
I2—C7—C12	119.2 (6)	C203—C204—C205	120.49 (14)
C8—C7—C12	120.2 (7)	C204—C205—C206	120.2 (8)
C7—C8—C9	120.5 (7)	C201—C206—C205	118.8 (12)
C8—C9—C10	120.0 (6)	I202—C207—C208	119.1 (11)
C9—C10—C11	120.50 (13)	I202—C207—C212	119.3 (11)
C9—C10—N2	119.73 (9)	C208—C207—C212	121.6 (13)
C11—C10—N2	119.77 (9)	C207—C208—C209	119.1 (12)
C10—C11—C12	119.6 (5)	C208—C209—C210	120.2 (8)
C7—C12—C11	119.2 (7)	N202—C210—C209	119.7 (1)
C4—N1—N2	131.7 (7)	N202—C210—C211	119.8 (1)
C10—N2—N1	123.9 (6)	C209—C210—C211	120.49 (14)
C10—N2—O1	113.4 (5)	C210—C211—C212	119.7 (8)
N1—N2—O1	122.5 (8)	C207—C212—C211	118.9 (12)

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N,N'-Bis(4-iodo­phenyl)­diazene N-oxide