N-Benzyl-2'-iodo­cinnamanilide and N-benzyl-2'-iodo-4'-methyl-2-phenyl­cinnamanilide

The aromatic ring of the cinnamic moiety in N-benzyl-2'-iodo­cinnamanilide, C₂₂H₁₈INO, (I), and N-benzyl-2'-iodo-4'-methyl-2-phenyl­cinnamanilide, C₂₉H₂₄INO, (II), makes a dihedral angle with the iodo­phenyl ring of 72.1 (2) and 81.0 (2)° in (I) and (II), respectively. In (I), mol­ecules exist as discrete components, while in (II), they form infinite chains along the b axis, through I...O non-bonded interactions.

S1. Comment

Cinnamoyl anilides are substrates for cyclization to biologically active five-membered 2-oxindole derivatives and six-membered 2-oxyquinolenes by photochemical methods. o-Iodinated anilides are used for the same reaction by electrochemical methods. The interest lies in the synthetic potential of these iodinated compounds and those of other acyclamides, which react with a wide range of nucleophilic compounds and therefore present new possibilities in the synthesis of heterocyclic compounds (Augustin et al., 1980). We have undertaken X-ray structure analysis of N-benzyl-2'-iodocinnamanilide, (I) and N-benzyl-2'-iodo-4'-methyl-2-phenylcinnamanilide, (II) to identify conformational features that favour cyclization. \scheme

The molecular geometry of the cinnamamide part of the title compounds agrees well with their analogues, N-methyl-2'-nitrocinnamanilide (Subramanian et al., 1999) and N-(4-chloro-2-iodophenyl)-N-methylcinnamamide (Renganayaki et al., 1999), reported by our group, and with other reported values (Iwamoto & Kashino, 1990; Iwamoto et al., 1989). The C—I distance [2.094 (4) in (I) and 2.101 (4) Å in (II)] is comparable with those reported in the literature (Elmali & Elerman, 1997; Banerjee et al., 1994).

The widening of the C1—C7—C8 angle [128.1 (4)°] in (I) is attributable to steric factors involving C2 and C8 [C2···C8 = 3.040 (6) Å]. Steric repulsion between phenyl rings A and D in (II) might contribute to further widening of this angle [130.8 (4)°].

In both compounds, the phenylmethyl ring B and the carbonyl group are syn-periplanar (cis) to each other [O10—C9—N11—C12 = 4.4 (6)° in (I) and 3.9 (6)° in (II)] and the phenyl ring C is anti-periplanar (trans) to the carbonyl group, with the O10—C9—N11—C19 torsion angle = -178.7 (4)° in (I) and -177.7 (4)° in (II). As seen from the torsion angle, the α,β-unsaturated carbonyl unit has the s-cis conformation. The dihedral angles between rings are A/B 62.0 (3), A/C 72.1 (2) and B/C 60.7 (2)° for (I), and 51.9 (3), 81.0 (2) and 48.0 (3)°, respectively, for (II). In (II), rings C and D are in a syn orientation, with an interplanar angle of 21.6 (2)°.

In (I), the packing of the molecules is stabilized by C—H···O and van der Waals interactions, while in (II) the packing is also stabilized by additional I···O interactions [I1···O10(-x + 1, y + 1/2, -z + 1/2) = 3.082 (3) Å].

S2. Experimental

For the prepapration of (I) the following procedure was employed. To a solution of o-iodoaniline (0.2 mol) and pyridine (0.2 mol) in dry benzene (50 ml), cinnamoyl bromide (0.2 mol in hexane) was added dropwise. The mixture was heated in a water bath at 333–343 K for 5 h and then the mixture was poured into 80–100 ml of water. The benzene layer was separated and washed repeatedly with water 3–4 times. The benzene was dried with magnesium sulfate and the benzene was then evaporated to obtain the anilide. For the benzylation of the anilide, NaH (0.2 mol) was taken in a round-bottomed flask. A solution of anilide (0.2 mol) in dry dimethylformamide (DMF; 50 ml) was added to the NaH. The reaction mixture was stirred for 15 min, and then benzyl bromide was added and stirred for 3 h. The reaction mixture was poured into water, extracted with ethylacetate and washed with water repeatedly to remove the DMF, and the compound was recrystallized from dichloromethane. For the preparation of (II), the synthesis procedure was same as for (I), with α-phenylcinnamoyl bromide as the starting material.

S3. Refinement

The H atoms were fixed at geometrically calculated distances (C—H = 0.96 Å for methyl and 0.93 Å for others) and were refined as riding on their parent atoms, with assigned isotropic displacement parameters of U(H)_iso = 1.5U_eq(C) for methyl and 1.2U_eq(C) for others.

Computing details

For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).

Figures

	Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms are drawn as small spheres of arbitrary radii.
	Fig. 2. The structure of (II) showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms are drawn as small spheres of arbitrary radii.

(I) N-benzyl-2'-iodocinnamanilide

Crystal data

C22H18INO	Dx = 1.535 Mg m^−3
Mr = 439.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 8192 reflections
a = 17.7759 (3) Å	θ = 1.7–28.4°
b = 9.0661 (2) Å	µ = 1.69 mm^−1
c = 23.5939 (3) Å	T = 293 K
V = 3802.35 (12) Å^3	Plate, colourless
Z = 8	0.28 × 0.14 × 0.06 mm
F(000) = 1744

Data collection

Siemens SMART CCD area detector diffractometer	4666 independent reflections
Radiation source: fine-focus sealed tube	2674 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.06
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 1.7°
ω scan	h = −23→13
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −11→12
Tmin = 0.721, Tmax = 0.901	l = −31→30
27608 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.023P)^2 + 2.0205P] where P = (Fo^2 + 2Fc^2)/3
4666 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −1.21 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 98% and 97% complete for (I) and (II) respectively. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible.

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. 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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.075929 (17)	−0.92867 (4)	0.388766 (11)	0.05872 (12)
C1	0.1481 (2)	−0.3688 (5)	0.41637 (16)	0.0444 (10)
C2	0.0760 (3)	−0.3718 (5)	0.43782 (19)	0.0638 (13)
H2A	0.0414	−0.4390	0.4234	0.077*
C3	0.0541 (3)	−0.2757 (6)	0.4808 (2)	0.0718 (15)
H3A	0.0055	−0.2798	0.4952	0.086*
C4	0.1041 (3)	−0.1757 (6)	0.50170 (19)	0.0706 (15)
H4A	0.0895	−0.1120	0.5306	0.085*
C5	0.1756 (3)	−0.1683 (6)	0.4806 (2)	0.0711 (15)
H5A	0.2093	−0.0991	0.4947	0.085*
C6	0.1976 (2)	−0.2645 (5)	0.43803 (18)	0.0575 (12)
H6A	0.2463	−0.2590	0.4237	0.069*
C7	0.1745 (2)	−0.4687 (5)	0.37182 (16)	0.0481 (11)
H7A	0.2259	−0.4673	0.3646	0.058*
C8	0.1345 (2)	−0.5601 (5)	0.34077 (16)	0.0436 (10)
H8A	0.0824	−0.5609	0.3442	0.052*
C9	0.1717 (2)	−0.6617 (5)	0.30040 (16)	0.0423 (10)
O10	0.24004 (15)	−0.6593 (4)	0.29306 (13)	0.0617 (9)
N11	0.12722 (17)	−0.7591 (3)	0.27217 (12)	0.0377 (8)
C12	0.1631 (2)	−0.8705 (4)	0.23522 (15)	0.0448 (10)
H12A	0.1371	−0.9638	0.2399	0.054*
H12B	0.2148	−0.8844	0.2474	0.054*
C13	0.1628 (2)	−0.8298 (5)	0.17298 (17)	0.0450 (10)
C14	0.1913 (3)	−0.6977 (6)	0.15458 (18)	0.0615 (13)
H14A	0.2111	−0.6315	0.1808	0.074*
C15	0.1912 (3)	−0.6615 (8)	0.0978 (2)	0.0852 (18)
H15A	0.2110	−0.5717	0.0860	0.102*
C16	0.1618 (3)	−0.7577 (10)	0.0589 (3)	0.098 (2)
H16A	0.1609	−0.7328	0.0207	0.118*
C17	0.1341 (4)	−0.8898 (9)	0.0766 (2)	0.097 (2)
H17A	0.1145	−0.9556	0.0501	0.116*
C18	0.1347 (3)	−0.9277 (6)	0.1336 (2)	0.0725 (14)
H18A	0.1161	−1.0187	0.1452	0.087*
C19	0.0469 (2)	−0.7693 (4)	0.27671 (16)	0.0364 (9)
C20	0.0022 (2)	−0.7193 (5)	0.23274 (17)	0.0475 (11)
H20A	0.0244	−0.6727	0.2019	0.057*
C21	−0.0748 (2)	−0.7374 (5)	0.23398 (19)	0.0542 (11)
H21A	−0.1040	−0.7063	0.2035	0.065*
C22	−0.1081 (2)	−0.8013 (5)	0.2802 (2)	0.0581 (13)
H22A	−0.1601	−0.8113	0.2814	0.070*
C23	−0.0651 (2)	−0.8511 (5)	0.32492 (18)	0.0530 (11)
H23A	−0.0880	−0.8936	0.3564	0.064*
C24	0.0125 (2)	−0.8372 (4)	0.32275 (15)	0.0400 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.05869 (19)	0.0728 (2)	0.04466 (16)	0.00328 (18)	−0.00243 (15)	0.01247 (15)
C1	0.046 (3)	0.044 (3)	0.043 (2)	−0.002 (2)	−0.004 (2)	0.002 (2)
C2	0.063 (3)	0.068 (3)	0.061 (3)	−0.015 (3)	0.009 (3)	−0.011 (2)
C3	0.071 (4)	0.084 (4)	0.060 (3)	−0.002 (3)	0.019 (3)	−0.008 (3)
C4	0.089 (4)	0.077 (4)	0.045 (3)	0.016 (3)	−0.005 (3)	−0.013 (3)
C5	0.072 (4)	0.075 (4)	0.066 (3)	0.001 (3)	−0.019 (3)	−0.021 (3)
C6	0.045 (3)	0.066 (3)	0.062 (3)	0.003 (2)	−0.009 (2)	−0.012 (2)
C7	0.040 (2)	0.052 (3)	0.052 (2)	−0.003 (2)	−0.005 (2)	0.001 (2)
C8	0.030 (2)	0.048 (3)	0.052 (2)	−0.003 (2)	−0.0002 (18)	0.000 (2)
C9	0.038 (2)	0.048 (3)	0.042 (2)	−0.003 (2)	−0.0014 (19)	0.0028 (19)
O10	0.0310 (17)	0.077 (2)	0.077 (2)	−0.0051 (16)	0.0060 (15)	−0.0131 (17)
N11	0.0304 (17)	0.041 (2)	0.0422 (18)	0.0009 (16)	0.0049 (15)	−0.0038 (15)
C12	0.040 (2)	0.038 (2)	0.056 (3)	0.003 (2)	0.008 (2)	0.0003 (19)
C13	0.036 (2)	0.051 (3)	0.048 (2)	0.005 (2)	0.0066 (19)	−0.004 (2)
C14	0.065 (3)	0.067 (4)	0.052 (3)	−0.005 (3)	0.005 (2)	0.010 (2)
C15	0.072 (4)	0.113 (5)	0.071 (4)	0.004 (4)	0.015 (3)	0.029 (3)
C16	0.077 (4)	0.162 (8)	0.057 (4)	0.033 (5)	0.011 (3)	0.016 (4)
C17	0.093 (5)	0.135 (7)	0.061 (4)	0.022 (5)	−0.013 (3)	−0.031 (4)
C18	0.078 (4)	0.076 (4)	0.064 (3)	0.002 (3)	−0.001 (3)	−0.012 (3)
C19	0.031 (2)	0.033 (2)	0.045 (2)	0.0000 (17)	−0.0004 (17)	−0.0053 (18)
C20	0.048 (3)	0.048 (3)	0.047 (2)	0.005 (2)	−0.003 (2)	0.0006 (19)
C21	0.048 (3)	0.055 (3)	0.059 (3)	0.010 (3)	−0.020 (2)	−0.004 (2)
C22	0.030 (2)	0.066 (3)	0.078 (3)	0.000 (2)	−0.007 (2)	−0.015 (3)
C23	0.039 (3)	0.062 (3)	0.058 (3)	−0.007 (2)	0.005 (2)	−0.002 (2)
C24	0.034 (2)	0.045 (3)	0.041 (2)	−0.0014 (19)	0.0006 (18)	−0.0076 (18)

Geometric parameters (Å, º)

I1—C24	2.094 (4)	C12—H12B	0.9700
C1—C2	1.379 (6)	C13—C14	1.371 (6)
C1—C6	1.389 (6)	C13—C18	1.379 (6)
C1—C7	1.464 (6)	C14—C15	1.379 (6)
C2—C3	1.392 (6)	C14—H14A	0.9300
C2—H2A	0.9300	C15—C16	1.369 (8)
C3—C4	1.362 (7)	C15—H15A	0.9300
C3—H3A	0.9300	C16—C17	1.361 (8)
C4—C5	1.366 (7)	C16—H16A	0.9300
C4—H4A	0.9300	C17—C18	1.388 (7)
C5—C6	1.386 (6)	C17—H17A	0.9300
C5—H5A	0.9300	C18—H18A	0.9300
C6—H6A	0.9300	C19—C20	1.384 (5)
C7—C8	1.315 (5)	C19—C24	1.391 (5)
C7—H7A	0.9300	C20—C21	1.379 (5)
C8—C9	1.481 (5)	C20—H20A	0.9300
C8—H8A	0.9300	C21—C22	1.369 (6)
C9—O10	1.227 (4)	C21—H21A	0.9300
C9—N11	1.360 (5)	C22—C23	1.379 (6)
N11—C19	1.434 (4)	C22—H22A	0.9300
N11—C12	1.479 (5)	C23—C24	1.386 (5)
C12—C13	1.514 (5)	C23—H23A	0.9300
C12—H12A	0.9700
C2—C1—C6	117.8 (4)	C14—C13—C18	118.9 (4)
C2—C1—C7	123.3 (4)	C14—C13—C12	121.2 (4)
C6—C1—C7	118.9 (4)	C18—C13—C12	119.9 (4)
C1—C2—C3	121.0 (5)	C13—C14—C15	120.9 (5)
C1—C2—H2A	119.5	C13—C14—H14A	119.5
C3—C2—H2A	119.5	C15—C14—H14A	119.5
C4—C3—C2	119.9 (5)	C16—C15—C14	120.1 (6)
C4—C3—H3A	120.1	C16—C15—H15A	120.0
C2—C3—H3A	120.1	C14—C15—H15A	120.0
C3—C4—C5	120.4 (5)	C17—C16—C15	119.5 (6)
C3—C4—H4A	119.8	C17—C16—H16A	120.2
C5—C4—H4A	119.8	C15—C16—H16A	120.2
C4—C5—C6	119.7 (5)	C16—C17—C18	120.8 (6)
C4—C5—H5A	120.1	C16—C17—H17A	119.6
C6—C5—H5A	120.1	C18—C17—H17A	119.6
C5—C6—C1	121.1 (4)	C13—C18—C17	119.8 (5)
C5—C6—H6A	119.5	C13—C18—H18A	120.1
C1—C6—H6A	119.5	C17—C18—H18A	120.1
C8—C7—C1	128.1 (4)	C20—C19—C24	118.6 (3)
C8—C7—H7A	116.0	C20—C19—N11	119.7 (3)
C1—C7—H7A	116.0	C24—C19—N11	121.6 (3)
C7—C8—C9	120.6 (4)	C21—C20—C19	121.0 (4)
C7—C8—H8A	119.7	C21—C20—H20A	119.5
C9—C8—H8A	119.7	C19—C20—H20A	119.5
O10—C9—N11	121.2 (4)	C22—C21—C20	119.8 (4)
O10—C9—C8	121.5 (4)	C22—C21—H21A	120.1
N11—C9—C8	117.3 (3)	C20—C21—H21A	120.1
C9—N11—C19	125.7 (3)	C21—C22—C23	120.6 (4)
C9—N11—C12	118.8 (3)	C21—C22—H22A	119.7
C19—N11—C12	115.4 (3)	C23—C22—H22A	119.7
N11—C12—C13	113.8 (3)	C22—C23—C24	119.6 (4)
N11—C12—H12A	108.8	C22—C23—H23A	120.2
C13—C12—H12A	108.8	C24—C23—H23A	120.2
N11—C12—H12B	108.8	C23—C24—C19	120.5 (4)
C13—C12—H12B	108.8	C23—C24—I1	118.2 (3)
H12A—C12—H12B	107.7	C19—C24—I1	121.3 (3)
C6—C1—C2—C3	−1.6 (7)	C12—C13—C14—C15	179.8 (4)
C7—C1—C2—C3	179.1 (4)	C13—C14—C15—C16	0.4 (8)
C1—C2—C3—C4	0.8 (8)	C14—C15—C16—C17	−1.1 (9)
C2—C3—C4—C5	0.4 (8)	C15—C16—C17—C18	0.5 (10)
C3—C4—C5—C6	−0.7 (8)	C14—C13—C18—C17	−1.4 (7)
C4—C5—C6—C1	−0.1 (7)	C12—C13—C18—C17	179.7 (4)
C2—C1—C6—C5	1.2 (7)	C16—C17—C18—C13	0.7 (9)
C7—C1—C6—C5	−179.4 (4)	C9—N11—C19—C20	106.5 (4)
C2—C1—C7—C8	9.4 (7)	C12—N11—C19—C20	−76.5 (5)
C6—C1—C7—C8	−169.9 (4)	C9—N11—C19—C24	−77.9 (5)
C1—C7—C8—C9	−175.3 (4)	C12—N11—C19—C24	99.2 (4)
C7—C8—C9—O10	−3.1 (6)	C24—C19—C20—C21	−0.7 (6)
C7—C8—C9—N11	176.2 (4)	N11—C19—C20—C21	175.2 (4)
O10—C9—N11—C19	−178.7 (4)	C19—C20—C21—C22	2.2 (7)
C8—C9—N11—C19	2.0 (6)	C20—C21—C22—C23	−1.6 (7)
O10—C9—N11—C12	4.4 (6)	C21—C22—C23—C24	−0.6 (7)
C8—C9—N11—C12	−174.9 (3)	C22—C23—C24—C19	2.2 (6)
C9—N11—C12—C13	−98.9 (4)	C22—C23—C24—I1	−175.4 (3)
C19—N11—C12—C13	83.8 (4)	C20—C19—C24—C23	−1.5 (6)
N11—C12—C13—C14	54.0 (5)	N11—C19—C24—C23	−177.3 (4)
N11—C12—C13—C18	−127.1 (4)	C20—C19—C24—I1	176.0 (3)
C18—C13—C14—C15	0.8 (7)	N11—C19—C24—I1	0.2 (5)

(II) N-benzyl-2'-iodo-4'-methyl-2-phenylcinnamanilide

Crystal data

C29H24INO	F(000) = 1064
Mr = 529.39	Dx = 1.414 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.8150 (2) Å	Cell parameters from 6014 reflections
b = 11.3607 (2) Å	θ = 1.9–28.3°
c = 20.2477 (5) Å	µ = 1.31 mm^−1
β = 91.271 (1)°	T = 293 K
V = 2487.14 (9) Å^3	Block, colourless
Z = 4	0.32 × 0.18 × 0.10 mm

Data collection

Siemens SMART CCD area detector diffractometer	6131 independent reflections
Radiation source: fine-focus sealed tube	2831 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.093
Detector resolution: 8.33 pixels mm^-1	θmax = 28.5°, θmin = 1.9°
ω scan	h = −10→14
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick,1996)	k = −15→14
Tmin = 0.674, Tmax = 0.897	l = −26→21
19536 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.028P)^2] where P = (Fo^2 + 2Fc^2)/3
6131 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.79 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 98% and 97% complete for (I) and (II) respectively. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible.

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. 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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.30203 (3)	0.07701 (3)	0.208241 (17)	0.06348 (14)
C1	0.5366 (3)	−0.2271 (4)	0.0928 (2)	0.0465 (11)
C2	0.5663 (4)	−0.1371 (4)	0.0505 (3)	0.0621 (13)
H2A	0.5576	−0.0596	0.0645	0.074*
C3	0.6089 (5)	−0.1588 (5)	−0.0123 (3)	0.0754 (15)
H3A	0.6270	−0.0963	−0.0401	0.091*
C4	0.6244 (4)	−0.2720 (6)	−0.0334 (3)	0.0777 (16)
H4A	0.6523	−0.2869	−0.0757	0.093*
C5	0.5988 (5)	−0.3627 (5)	0.0080 (3)	0.0757 (16)
H5A	0.6113	−0.4398	−0.0057	0.091*
C6	0.5540 (4)	−0.3408 (4)	0.0709 (3)	0.0644 (14)
H6A	0.5356	−0.4037	0.0984	0.077*
C7	0.4963 (4)	−0.2007 (3)	0.1607 (2)	0.0465 (11)
H7A	0.5319	−0.1337	0.1794	0.056*
C8	0.4173 (3)	−0.2571 (3)	0.1996 (2)	0.0417 (10)
C9	0.4122 (4)	−0.2184 (3)	0.2702 (2)	0.0462 (11)
O10	0.5017 (3)	−0.2287 (3)	0.30675 (16)	0.0706 (10)
N11	0.3051 (3)	−0.1696 (3)	0.29260 (18)	0.0492 (9)
C12	0.2988 (4)	−0.1217 (4)	0.3603 (2)	0.0578 (12)
H12A	0.2632	−0.0434	0.3580	0.069*
H12B	0.3823	−0.1141	0.3783	0.069*
C13	0.2247 (4)	−0.1946 (4)	0.4067 (2)	0.0555 (12)
C14	0.2701 (5)	−0.2967 (5)	0.4324 (3)	0.0810 (16)
H14A	0.3498	−0.3203	0.4223	0.097*
C15	0.2007 (8)	−0.3654 (6)	0.4731 (4)	0.112 (2)
H15A	0.2345	−0.4346	0.4902	0.134*
C16	0.0835 (8)	−0.3350 (7)	0.4891 (4)	0.123 (3)
H16A	0.0369	−0.3830	0.5162	0.147*
C17	0.0364 (6)	−0.2334 (8)	0.4647 (4)	0.128 (3)
H17A	−0.0430	−0.2102	0.4755	0.153*
C18	0.1061 (5)	−0.1639 (6)	0.4237 (3)	0.099 (2)
H18A	0.0721	−0.0945	0.4070	0.119*
C19	0.1954 (4)	−0.1590 (4)	0.2527 (2)	0.0486 (11)
C20	0.1079 (4)	−0.2478 (4)	0.2547 (2)	0.0616 (13)
H20A	0.1217	−0.3129	0.2817	0.074*
C21	0.0013 (4)	−0.2407 (5)	0.2173 (3)	0.0769 (16)
H21A	−0.0566	−0.3010	0.2190	0.092*
C22	−0.0211 (4)	−0.1446 (6)	0.1769 (3)	0.0774 (16)
C23	0.0660 (4)	−0.0557 (4)	0.1751 (2)	0.0657 (14)
H23A	0.0516	0.0093	0.1481	0.079*
C24	0.1740 (4)	−0.0617 (4)	0.2127 (2)	0.0555 (12)
C25	−0.1381 (5)	−0.1376 (6)	0.1355 (3)	0.117 (2)
H25A	−0.1875	−0.2064	0.1430	0.175*
H25B	−0.1177	−0.1335	0.0896	0.175*
H25C	−0.1837	−0.0687	0.1474	0.175*
C26	0.3386 (3)	−0.3585 (4)	0.1799 (2)	0.0462 (11)
C27	0.3349 (4)	−0.4574 (4)	0.2199 (3)	0.0646 (14)
H27A	0.3832	−0.4599	0.2584	0.078*
C28	0.2620 (5)	−0.5506 (4)	0.2038 (3)	0.0789 (17)
H28A	0.2623	−0.6166	0.2310	0.095*
C29	0.1898 (6)	−0.5490 (5)	0.1496 (4)	0.095 (2)
H29A	0.1391	−0.6129	0.1395	0.113*
C30	0.1908 (5)	−0.4524 (6)	0.1089 (3)	0.092 (2)
H30A	0.1408	−0.4513	0.0709	0.111*
C31	0.2662 (4)	−0.3559 (5)	0.1238 (2)	0.0656 (13)
H31A	0.2670	−0.2907	0.0960	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0630 (2)	0.0584 (2)	0.0695 (3)	0.00272 (17)	0.01212 (14)	0.00739 (19)
C1	0.045 (3)	0.046 (3)	0.049 (3)	−0.0006 (19)	−0.003 (2)	0.000 (2)
C2	0.073 (3)	0.057 (3)	0.056 (4)	−0.002 (2)	0.003 (3)	0.005 (3)
C3	0.093 (4)	0.079 (4)	0.054 (4)	−0.004 (3)	0.013 (3)	0.013 (3)
C4	0.075 (4)	0.106 (5)	0.052 (4)	0.002 (3)	0.011 (3)	−0.011 (4)
C5	0.091 (4)	0.059 (3)	0.078 (5)	0.000 (3)	0.027 (3)	−0.017 (3)
C6	0.076 (3)	0.055 (3)	0.063 (4)	0.005 (2)	0.020 (3)	0.003 (3)
C7	0.052 (3)	0.040 (2)	0.048 (3)	−0.002 (2)	0.001 (2)	−0.006 (2)
C8	0.042 (2)	0.041 (2)	0.043 (3)	0.0042 (19)	0.001 (2)	0.000 (2)
C9	0.050 (3)	0.040 (2)	0.049 (3)	−0.002 (2)	0.002 (2)	0.004 (2)
O10	0.063 (2)	0.097 (2)	0.052 (2)	0.0154 (18)	−0.0164 (17)	−0.0143 (19)
N11	0.045 (2)	0.058 (2)	0.045 (3)	−0.0010 (17)	0.0021 (18)	−0.0032 (19)
C12	0.063 (3)	0.062 (3)	0.049 (4)	0.004 (2)	−0.001 (2)	−0.009 (3)
C13	0.062 (3)	0.069 (3)	0.035 (3)	0.007 (2)	0.003 (2)	−0.003 (3)
C14	0.091 (4)	0.082 (4)	0.070 (5)	0.014 (3)	0.010 (3)	0.014 (3)
C15	0.164 (7)	0.083 (4)	0.089 (6)	0.011 (5)	0.018 (5)	0.020 (4)
C16	0.153 (8)	0.133 (7)	0.084 (6)	−0.027 (6)	0.038 (5)	0.027 (5)
C17	0.098 (5)	0.183 (8)	0.103 (7)	0.002 (5)	0.035 (4)	0.036 (6)
C18	0.083 (4)	0.126 (5)	0.089 (5)	0.028 (4)	0.022 (4)	0.038 (4)
C19	0.042 (3)	0.061 (3)	0.043 (3)	−0.001 (2)	0.011 (2)	−0.005 (2)
C20	0.052 (3)	0.074 (3)	0.059 (4)	−0.005 (3)	0.009 (2)	−0.001 (3)
C21	0.052 (3)	0.104 (4)	0.076 (5)	−0.021 (3)	0.015 (3)	−0.013 (4)
C22	0.044 (3)	0.129 (5)	0.060 (4)	−0.002 (3)	0.006 (3)	−0.008 (4)
C23	0.052 (3)	0.091 (4)	0.054 (4)	0.012 (3)	0.006 (2)	0.012 (3)
C24	0.046 (3)	0.067 (3)	0.054 (3)	0.001 (2)	0.011 (2)	−0.002 (3)
C25	0.058 (4)	0.219 (7)	0.073 (5)	−0.007 (4)	−0.008 (3)	−0.004 (5)
C26	0.039 (2)	0.056 (3)	0.044 (3)	−0.003 (2)	0.002 (2)	−0.004 (2)
C27	0.061 (3)	0.054 (3)	0.079 (4)	−0.005 (2)	−0.003 (3)	0.003 (3)
C28	0.061 (3)	0.065 (4)	0.111 (6)	−0.011 (3)	0.007 (3)	0.007 (3)
C29	0.074 (4)	0.083 (5)	0.127 (7)	−0.025 (3)	0.015 (4)	−0.031 (4)
C30	0.062 (4)	0.141 (6)	0.074 (5)	−0.019 (4)	−0.010 (3)	−0.036 (4)
C31	0.060 (3)	0.090 (4)	0.046 (4)	−0.011 (3)	−0.002 (2)	−0.009 (3)

Geometric parameters (Å, º)

I1—C24	2.101 (4)	C14—C15	1.371 (8)
C1—C2	1.377 (6)	C15—C16	1.359 (9)
C1—C6	1.380 (6)	C16—C17	1.351 (9)
C1—C7	1.481 (6)	C17—C18	1.382 (8)
C2—C3	1.384 (7)	C19—C20	1.384 (6)
C3—C4	1.366 (7)	C19—C24	1.386 (6)
C4—C5	1.361 (7)	C20—C21	1.368 (6)
C5—C6	1.394 (7)	C21—C22	1.381 (7)
C7—C8	1.339 (6)	C22—C23	1.382 (7)
C8—C26	1.481 (5)	C22—C25	1.504 (6)
C8—C9	1.499 (6)	C23—C24	1.382 (6)
C9—O10	1.211 (4)	C26—C31	1.365 (5)
C9—N11	1.370 (5)	C26—C27	1.387 (6)
N11—C19	1.426 (5)	C27—C28	1.355 (6)
N11—C12	1.478 (5)	C28—C29	1.332 (7)
C12—C13	1.498 (6)	C29—C30	1.374 (7)
C13—C14	1.359 (6)	C30—C31	1.395 (7)
C13—C18	1.380 (7)
C2—C1—C6	117.3 (5)	C17—C16—C15	118.4 (7)
C2—C1—C7	120.3 (4)	C16—C17—C18	120.2 (7)
C6—C1—C7	122.3 (4)	C13—C18—C17	121.8 (6)
C1—C2—C3	121.8 (5)	C20—C19—C24	119.5 (4)
C4—C3—C2	120.0 (5)	C20—C19—N11	118.8 (4)
C5—C4—C3	119.5 (5)	C24—C19—N11	121.6 (4)
C4—C5—C6	120.4 (5)	C21—C20—C19	120.6 (5)
C1—C6—C5	120.9 (5)	C20—C21—C22	120.6 (5)
C8—C7—C1	130.8 (4)	C21—C22—C23	118.8 (4)
C7—C8—C26	125.8 (4)	C21—C22—C25	120.4 (6)
C7—C8—C9	117.3 (4)	C23—C22—C25	120.8 (6)
C26—C8—C9	116.9 (4)	C24—C23—C22	121.2 (5)
O10—C9—N11	120.5 (4)	C23—C24—C19	119.3 (4)
O10—C9—C8	120.6 (4)	C23—C24—I1	119.3 (4)
N11—C9—C8	118.9 (4)	C19—C24—I1	121.4 (3)
C9—N11—C19	123.0 (4)	C31—C26—C27	118.7 (4)
C9—N11—C12	120.8 (3)	C31—C26—C8	121.5 (4)
C19—N11—C12	116.1 (3)	C27—C26—C8	119.8 (4)
N11—C12—C13	114.5 (4)	C28—C27—C26	121.1 (5)
C14—C13—C18	116.8 (5)	C29—C28—C27	121.0 (6)
C14—C13—C12	121.2 (5)	C28—C29—C30	119.5 (5)
C18—C13—C12	121.9 (5)	C29—C30—C31	120.7 (5)
C13—C14—C15	121.2 (6)	C26—C31—C30	119.0 (5)
C16—C15—C14	121.6 (7)