N,N'-Bis(3-iodo­phen­yl)ethyl­enediimine

In the crystal structure of the title compound, C₁₄H₁₀I₂N₂, the mol­ecule lies on a crystallographic inversion center, and hence the two imine groups are mutually trans.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.021
• wR factor = 0.056
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.07
PLAT431_ALERT_2_C Short Inter HL..A Contact  I1     ..  N1      ..       3.23 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: XCIF (Bruker, 2001).

N,N'-Bis(3-iodophenyl)ethylenediimine

Crystal data

C14H10I2N2	F(000) = 856
Mr = 460.04	Dx = 2.159 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 879 reflections
a = 16.262 (4) Å	θ = 2.6–28.3°
b = 4.7074 (11) Å	µ = 4.43 mm^−1
c = 18.708 (4) Å	T = 193 K
β = 98.829 (4)°	Tabular, yellow
V = 1415.2 (6) Å^3	0.34 × 0.24 × 0.06 mm
Z = 4

Data collection

Siemens Platform CCD area-detector diffractometer	1760 independent reflections
Radiation source: normal-focus sealed tube	1607 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Profile data from ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: integration (XPREP in SHELXTL; Bruker, 2001)	h = −21→21
Tmin = 0.295, Tmax = 0.771	k = −6→6
6991 measured reflections	l = −24→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.021	H-atom parameters constrained
wR(F^2) = 0.056	w = 1/[σ^2(Fo^2) + (0.0295P)^2 + 1.6495P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
1760 reflections	Δρmax = 0.72 e Å^−3
88 parameters	Δρmin = −0.79 e Å^−3
0 restraints	Extinction correction: SHELXTL (Bruker, 2001), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (2)

Special details

Experimental. One distinct cell was identified using SMART (Bruker, 2001). Four frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2001) then corrected for absorption by integration using SHELXTL/XPREP (Bruker, 2001) before using SAINT/SADABS (Bruker, 2001) to sort, merge, and scale the combined data. A series of identical frames was collected twice during the experiment to monitor decay. No decay correction was applied.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Systematic conditions suggested the ambiguous space group. Structure was phased by direct methods. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F². The highest peak in the final difference Fourier map was in the vicinity of atom I1; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude or resolution.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.03012 (13)	0.5940 (5)	0.52037 (12)	0.0298 (5)
H1	0.0858	0.5914	0.5107	0.095 (13)*
C2	0.07114 (13)	0.9415 (5)	0.60663 (11)	0.0283 (4)
C3	0.15177 (14)	0.9815 (5)	0.59080 (13)	0.0322 (5)
H3	0.1700	0.8788	0.5524	0.053 (8)*
C4	0.20477 (13)	1.1712 (5)	0.63129 (12)	0.0275 (4)
C5	0.17915 (16)	1.3240 (5)	0.68736 (13)	0.0338 (5)
H5	0.2157	1.4550	0.7147	0.038 (7)*
C6	0.09907 (19)	1.2823 (5)	0.70278 (15)	0.0388 (6)
H6	0.0810	1.3847	0.7413	0.049 (8)*
C7	0.04556 (14)	1.0938 (5)	0.66277 (12)	0.0314 (5)
H7	−0.0091	1.0682	0.6737	0.039 (7)*
I1	0.325791 (9)	1.22825 (4)	0.607495 (9)	0.03758 (10)
N1	0.01194 (15)	0.7582 (4)	0.56736 (15)	0.0438 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0242 (10)	0.0308 (11)	0.0345 (12)	−0.0052 (9)	0.0046 (9)	−0.0054 (9)
C2	0.0266 (10)	0.0289 (10)	0.0296 (11)	−0.0066 (8)	0.0046 (8)	−0.0053 (8)
C3	0.0278 (10)	0.0346 (11)	0.0355 (12)	−0.0065 (9)	0.0084 (9)	−0.0107 (9)
C4	0.0252 (11)	0.0271 (10)	0.0298 (11)	−0.0034 (8)	0.0023 (8)	0.0015 (8)
C5	0.0355 (12)	0.0360 (11)	0.0288 (11)	−0.0104 (10)	0.0015 (9)	−0.0079 (9)
C6	0.0406 (15)	0.0433 (14)	0.0340 (13)	−0.0096 (10)	0.0110 (11)	−0.0150 (10)
C7	0.0294 (11)	0.0359 (12)	0.0299 (11)	−0.0069 (9)	0.0076 (9)	−0.0061 (9)
I1	0.02493 (12)	0.04507 (13)	0.04290 (14)	−0.01160 (6)	0.00572 (7)	−0.00591 (6)
N1	0.0263 (11)	0.0552 (15)	0.0528 (15)	−0.0174 (8)	0.0148 (10)	−0.0272 (10)

Geometric parameters (Å, º)

C1—N1	1.240 (3)	C4—C5	1.388 (3)
C1—C1^i	1.447 (4)	C4—I1	2.101 (2)
C1—H1	0.9500	C5—C6	1.390 (4)
C2—C7	1.387 (3)	C5—H5	0.9500
C2—C3	1.401 (3)	C6—C7	1.380 (3)
C2—N1	1.412 (3)	C6—H6	0.9500
C3—C4	1.383 (3)	C7—H7	0.9500
C3—H3	0.9500
N1—C1—C1^i	122.6 (3)	C5—C4—I1	119.59 (16)
N1—C1—H1	118.7	C4—C5—C6	118.9 (2)
C1^i—C1—H1	118.7	C4—C5—H5	120.6
C7—C2—C3	119.3 (2)	C6—C5—H5	120.6
C7—C2—N1	116.7 (2)	C7—C6—C5	120.7 (2)
C3—C2—N1	123.9 (2)	C7—C6—H6	119.6
C4—C3—C2	119.7 (2)	C5—C6—H6	119.6
C4—C3—H3	120.1	C6—C7—C2	120.4 (2)
C2—C3—H3	120.1	C6—C7—H7	119.8
C3—C4—C5	121.0 (2)	C2—C7—H7	119.8
C3—C4—I1	119.45 (17)	C1—N1—C2	122.1 (2)
C7—C2—C3—C4	0.1 (4)	C5—C6—C7—C2	0.3 (4)
N1—C2—C3—C4	178.4 (2)	C3—C2—C7—C6	−0.2 (4)
C2—C3—C4—C5	−0.3 (4)	N1—C2—C7—C6	−178.6 (2)
C2—C3—C4—I1	179.68 (17)	C1^i—C1—N1—C2	−179.8 (3)
C3—C4—C5—C6	0.4 (4)	C7—C2—N1—C1	−173.6 (3)
I1—C4—C5—C6	−179.5 (2)	C3—C2—N1—C1	8.1 (4)
C4—C5—C6—C7	−0.5 (4)

Symmetry code: (i) −x, −y+1, −z+1.