(3-Iodo­phen­yl)[2-(3-iodo­phenyl­imino)-1-methyl­propyl­idene]amine

In the crystal structure of the title compound, C₁₆H₁₄I₂N₂, 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)= 0.005 Å
• R factor = 0.026
• wR factor = 0.068
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

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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).

(3-Iodophenyl)[2-(3-iodophenylimino)-1-methylpropylidene]amine

Crystal data

C16H14I2N2	F(000) = 920
Mr = 488.09	Dx = 1.939 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 950 reflections
a = 11.481 (2) Å	θ = 3.1–25.9°
b = 9.2619 (19) Å	µ = 3.75 mm^−1
c = 15.723 (3) Å	T = 193 K
V = 1672.0 (6) Å^3	Tabular, yellow
Z = 4	0.22 × 0.20 × 0.08 mm

Data collection

Siemens Platform/CCD diffractometer	1530 independent reflections
Radiation source: normal-focus sealed tube	1067 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Profile data from ω scans	θmax = 25.4°, θmin = 2.6°
Absorption correction: integration (SHELXTL/XPREP; Bruker, 2001)	h = −13→13
Tmin = 0.496, Tmax = 0.754	k = −10→11
13409 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.068	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0352P)^2 + 0.4421P] where P = (Fo^2 + 2Fc^2)/3
1530 reflections	(Δ/σ)max = 0.001
92 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.68 e Å^−3

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). 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 unambiguous 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 peaks in the final difference Fourier map were 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.

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

	x	y	z	Uiso*/Ueq
C1	0.7835 (2)	0.1273 (4)	0.1714 (2)	0.0441 (9)
H1	0.8515	0.1794	0.1873	0.053*
C2	0.6907 (3)	0.1167 (4)	0.2271 (2)	0.0494 (9)
C3	0.5911 (3)	0.0412 (4)	0.2049 (3)	0.0595 (11)
H3	0.5279	0.0334	0.2435	0.071*
C4	0.5852 (3)	−0.0224 (4)	0.1258 (3)	0.0598 (10)
H4	0.5170	−0.0738	0.1099	0.072*
C5	0.6773 (3)	−0.0125 (4)	0.0687 (3)	0.0547 (10)
H5	0.6723	−0.0561	0.0141	0.066*
C6	0.7773 (3)	0.0625 (4)	0.0930 (2)	0.0454 (9)
C7	0.9521 (3)	−0.0131 (3)	0.03200 (19)	0.0368 (7)
C8	0.9615 (3)	−0.1461 (4)	0.0858 (2)	0.0509 (9)
H8A	0.8979	−0.1475	0.1274	0.076*
H8B	1.0364	−0.1460	0.1157	0.076*
H8C	0.9564	−0.2319	0.0495	0.076*
I1	0.70369 (2)	0.21950 (4)	0.345673 (17)	0.07121 (15)
N1	0.8710 (2)	0.0793 (3)	0.03373 (17)	0.0445 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0329 (18)	0.047 (2)	0.052 (2)	0.0080 (15)	0.0083 (15)	0.0165 (16)
C2	0.047 (2)	0.048 (2)	0.053 (2)	0.0140 (17)	0.0112 (16)	0.0165 (17)
C3	0.040 (2)	0.061 (3)	0.078 (3)	0.0112 (19)	0.0229 (19)	0.028 (2)
C4	0.041 (2)	0.052 (2)	0.087 (3)	−0.0030 (18)	0.012 (2)	0.006 (2)
C5	0.048 (2)	0.043 (2)	0.073 (2)	−0.0030 (17)	0.0076 (19)	0.0015 (19)
C6	0.040 (2)	0.040 (2)	0.057 (2)	0.0044 (16)	0.0132 (14)	0.0121 (16)
C7	0.0340 (17)	0.0394 (19)	0.0371 (17)	−0.0046 (14)	0.0012 (13)	0.0004 (15)
C8	0.045 (2)	0.051 (2)	0.056 (2)	0.0035 (17)	0.0120 (16)	0.0143 (18)
I1	0.0733 (2)	0.0870 (3)	0.05331 (19)	0.01967 (15)	0.01925 (12)	0.00775 (14)
N1	0.0391 (16)	0.0447 (16)	0.0499 (17)	0.0022 (13)	0.0090 (13)	0.0039 (14)

Geometric parameters (Å, º)

C1—C6	1.372 (5)	C5—C6	1.395 (5)
C1—C2	1.384 (4)	C5—H5	0.9500
C1—H1	0.9500	C6—N1	1.433 (4)
C2—C3	1.386 (5)	C7—N1	1.264 (4)
C2—I1	2.098 (4)	C7—C8	1.499 (4)
C3—C4	1.378 (6)	C7—C7^i	1.511 (6)
C3—H3	0.9500	C8—H8A	0.9800
C4—C5	1.390 (5)	C8—H8B	0.9800
C4—H4	0.9500	C8—H8C	0.9800
C6—C1—C2	119.8 (3)	C6—C5—H5	120.6
C6—C1—H1	120.1	C1—C6—C5	120.5 (3)
C2—C1—H1	120.1	C1—C6—N1	119.8 (3)
C1—C2—C3	120.8 (3)	C5—C6—N1	119.6 (3)
C1—C2—I1	118.4 (3)	N1—C7—C8	126.7 (3)
C3—C2—I1	120.8 (3)	N1—C7—C7^i	116.2 (3)
C4—C3—C2	119.0 (3)	C8—C7—C7^i	117.1 (3)
C4—C3—H3	120.5	C7—C8—H8A	109.5
C2—C3—H3	120.5	C7—C8—H8B	109.5
C3—C4—C5	121.2 (4)	H8A—C8—H8B	109.5
C3—C4—H4	119.4	C7—C8—H8C	109.5
C5—C4—H4	119.4	H8A—C8—H8C	109.5
C4—C5—C6	118.8 (4)	H8B—C8—H8C	109.5
C4—C5—H5	120.6	C7—N1—C6	119.6 (3)
C6—C1—C2—C3	0.0 (5)	C2—C1—C6—N1	177.0 (3)
C6—C1—C2—I1	−179.4 (3)	C4—C5—C6—C1	−1.1 (5)
C1—C2—C3—C4	−0.6 (5)	C4—C5—C6—N1	−177.3 (3)
I1—C2—C3—C4	178.8 (3)	C8—C7—N1—C6	1.4 (5)
C2—C3—C4—C5	0.4 (5)	C7^i—C7—N1—C6	−179.6 (3)
C3—C4—C5—C6	0.5 (6)	C1—C6—N1—C7	92.4 (4)
C2—C1—C6—C5	0.8 (5)	C5—C6—N1—C7	−91.4 (4)

Symmetry code: (i) −x+2, −y, −z.