Nine isomeric nitrobenzylidene-iodoanilines: interplay of C—H⋯O hydrogen bonds, iodo⋯nitro interactions and aromatic π⋯π stacking interactions

Glidewell, C.; Howie, R.A.; Low, J.N.; Skakle, J.M.S.; Wardell, S.M.S.V.; Wardell, J.L.

doi:10.1107/S0108768102009941

Nine isomeric nitrobenzylidene-iodoanilines: interplay of C—HO hydrogen bonds, iodonitro interactions and aromatic ππ stacking interactions

C. Glidewell, R. A. Howie, J. N. Low, J. M. S. Skakle, S. M. S. V. Wardell and J. L. Wardell

Nine isomeric nitrobenzylidene-iodoanilines, O₂NC₆H₄CH= NC₆H₄I [(I)–(IX)], have been synthesized and the structures of all except 4-nitrobenzylidene-4′-iodoaniline (IX) have been analyzed. 2-Nitrobenzylidene-2′-iodoaniline (I) contains isolated molecules, while 3-nitrobenzylidene-2′-iodoaniline (II) and 2-nitrobenzylidene-3′-iodoaniline (IV) both contain chains of molecules linked by C—H

O hydrogen bonds: similar chains in 4-nitrobenzylidene-2′-iodoaniline (III) are further linked by aromatic π

π stacking interactions, forming sheets. In both 3-nitrobenzylidene-3′-iodoaniline and 4-nitrobenzylidene-3′-iodoaniline, (V) and (VI), a combination of C—H

O hydrogen bonds and iodo

nitro interactions generates molecular ladders that are linked into sheets by aromatic π

π stacking interactions, while in 2-nitrobenzylidene-4′-iodoaniline and 3-nitrobenzylidene-4′-iodoaniline, (VII) and (VIII), which both crystallize with Z′ = 2 in C2/c and P $\bar 1$ , respectively, the combination of C—H

O hydrogen bonds and iodo

nitro interactions generates sheets, which in (VIII) are further linked by π

π stacking interactions to form a three-dimensional structure. The 4,4′-isomer (IX) crystallizes in Fdd2 with Z′ = 2, but both molecules are intractably disordered.

Keywords: nitrobenzylidene-iodoanilines; hydrogen bonds; iodo

nitro interactions; π

π stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102009941/na0138sup1.cif Contains datablocks global, I, II, III, IV, V, VI, VII, VIII
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102009941/na0138Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102009941/na0138IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102009941/na0138IIIsup4.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102009941/na0138IVsup5.hkl Contains datablock IV
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102009941/na0138Vsup6.hkl Contains datablock V
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102009941/na0138VIsup7.hkl Contains datablock VI
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102009941/na0138VIIsup8.hkl Contains datablock VII
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102009941/na0138VIIIsup9.hkl Contains datablock VIII

CCDC references: 195809; 195810; 195811; 195812; 195813; 195814; 195815; 195816

Comment top

In full text version

Experimental top

In full text version

Computing details top

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999).

Figures top

In full text version

(I) 2-Nitrobenzylidene-2'-iodoaniline top

Crystal data top

C₁₃H₉IN₂O₂	F(000) = 680
M_r = 352.12	D_x = 1.880 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2777 reflections
a = 8.0664 (4) Å	θ = 3.1–27.5°
b = 10.7191 (5) Å	µ = 2.57 mm⁻¹
c = 14.5692 (9) Å	T = 120 K
β = 99.026 (2)°	Lath, brown
V = 1244.12 (11) Å³	0.17 × 0.04 × 0.02 mm
Z = 4

Data collection top

Kappa-CCD diffractometer	2777 independent reflections
Radiation source: fine-focus sealed X-ray tube	1865 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −10→9
T_min = 0.929, T_max = 0.950	k = −12→13
7432 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.005P)²] where P = (F_o² + 2F_c²)/3
2777 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 1.07 e Å⁻³
0 restraints	Δρ_min = −1.01 e Å⁻³

Crystal data top

C₁₃H₉IN₂O₂	V = 1244.12 (11) Å³
M_r = 352.12	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0664 (4) Å	µ = 2.57 mm⁻¹
b = 10.7191 (5) Å	T = 120 K
c = 14.5692 (9) Å	0.17 × 0.04 × 0.02 mm
β = 99.026 (2)°

Data collection top

Kappa-CCD diffractometer	2777 independent reflections
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	1865 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.950	R_int = 0.057
7432 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 0.98	Δρ_max = 1.07 e Å⁻³
2777 reflections	Δρ_min = −1.01 e Å⁻³
163 parameters

Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used.

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	U_iso*/U_eq
C11	0.3346 (5)	1.1134 (4)	0.4526 (3)	0.0166 (9)
C12	0.3667 (5)	1.1561 (4)	0.3666 (3)	0.0194 (9)
N2	0.3141 (4)	1.0804 (3)	0.2820 (3)	0.0229 (9)
O1	0.2901 (4)	1.1346 (3)	0.2069 (2)	0.0345 (8)
O2	0.3006 (4)	0.9680 (3)	0.2912 (2)	0.0305 (8)
C13	0.4521 (5)	1.2662 (4)	0.3560 (3)	0.0215 (10)
C14	0.5115 (5)	1.3358 (4)	0.4345 (3)	0.0228 (10)
C15	0.4869 (5)	1.2944 (4)	0.5210 (3)	0.0241 (11)
C16	0.3971 (5)	1.1861 (4)	0.5295 (3)	0.0227 (10)
C17	0.2294 (5)	1.0047 (4)	0.4658 (3)	0.0186 (10)
N1	0.2512 (4)	0.9494 (3)	0.5437 (2)	0.0195 (8)
C21	0.1472 (5)	0.8477 (4)	0.5581 (3)	0.0184 (9)
C22	0.1153 (5)	0.8248 (4)	0.6480 (3)	0.0178 (9)
C23	0.0199 (5)	0.7245 (4)	0.6682 (3)	0.0230 (10)
C24	−0.0452 (5)	0.6421 (4)	0.5991 (3)	0.0233 (10)
C25	−0.0143 (5)	0.6631 (4)	0.5094 (3)	0.0261 (10)
C26	0.0806 (5)	0.7638 (4)	0.4889 (3)	0.0222 (10)
I2	0.21433 (4)	0.94987 (3)	0.753943 (19)	0.02802 (12)
H13	0.4695	1.2933	0.2962	0.026*
H14	0.5692	1.4119	0.4288	0.027*
H15	0.5317	1.3404	0.5750	0.029*
H16	0.3777	1.1607	0.5894	0.027*
H17	0.1465	0.9763	0.4166	0.022*
H23	−0.0009	0.7121	0.7299	0.028*
H24	−0.1100	0.5724	0.6128	0.028*
H25	−0.0592	0.6073	0.4612	0.031*
H26	0.1007	0.7760	0.4270	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.017 (2)	0.016 (2)	0.018 (2)	0.0051 (18)	0.0062 (17)	0.0029 (19)
C12	0.016 (2)	0.023 (2)	0.020 (2)	0.007 (2)	0.0032 (17)	−0.002 (2)
N2	0.024 (2)	0.029 (2)	0.017 (2)	0.0077 (17)	0.0088 (16)	0.0038 (18)
O1	0.046 (2)	0.043 (2)	0.0148 (18)	0.0008 (17)	0.0030 (14)	0.0067 (17)
O2	0.040 (2)	0.028 (2)	0.0234 (19)	−0.0020 (15)	0.0055 (14)	−0.0056 (15)
C13	0.021 (2)	0.025 (2)	0.020 (2)	0.007 (2)	0.0061 (18)	0.009 (2)
C14	0.020 (2)	0.018 (2)	0.030 (3)	−0.001 (2)	0.0032 (19)	0.000 (2)
C15	0.025 (3)	0.024 (3)	0.023 (3)	−0.002 (2)	0.0014 (19)	−0.007 (2)
C16	0.021 (2)	0.027 (3)	0.020 (3)	0.006 (2)	0.0038 (18)	0.002 (2)
C17	0.020 (2)	0.019 (2)	0.017 (2)	0.0051 (18)	0.0048 (18)	0.0005 (19)
N1	0.022 (2)	0.0192 (19)	0.018 (2)	0.0010 (17)	0.0052 (15)	−0.0012 (17)
C21	0.017 (2)	0.020 (2)	0.018 (2)	0.0044 (19)	0.0013 (17)	−0.003 (2)
C22	0.016 (2)	0.021 (2)	0.016 (2)	0.0047 (19)	0.0010 (17)	−0.0015 (19)
C23	0.023 (2)	0.028 (3)	0.018 (2)	0.010 (2)	0.0056 (19)	0.005 (2)
C24	0.022 (2)	0.021 (2)	0.026 (3)	0.001 (2)	0.0021 (19)	0.001 (2)
C25	0.030 (3)	0.021 (2)	0.025 (3)	0.001 (2)	−0.002 (2)	−0.003 (2)
C26	0.030 (3)	0.022 (3)	0.014 (2)	0.009 (2)	0.0008 (19)	0.002 (2)
I2	0.0335 (2)	0.0343 (2)	0.01664 (18)	−0.00237 (15)	0.00515 (12)	−0.00426 (15)

Geometric parameters (Å, º) top

C11—C16	1.393 (6)	C17—N1	1.268 (5)
C11—C12	1.395 (5)	C17—H17	0.9500
C11—C17	1.471 (6)	N1—C21	1.412 (5)
C12—C13	1.388 (6)	C21—C26	1.394 (6)
C12—N2	1.481 (5)	C21—C22	1.396 (5)
N2—O2	1.220 (4)	C22—C23	1.380 (6)
N2—O1	1.227 (4)	C22—I2	2.105 (4)
C13—C14	1.386 (6)	C23—C24	1.379 (6)
C13—H13	0.9500	C23—H23	0.9500
C14—C15	1.379 (6)	C24—C25	1.387 (6)
C14—H14	0.9500	C24—H24	0.9500
C15—C16	1.384 (5)	C25—C26	1.383 (6)
C15—H15	0.9500	C25—H25	0.9500
C16—H16	0.9500	C26—H26	0.9500

C16—C11—C12	116.3 (4)	N1—C17—H17	120.5
C16—C11—C17	118.8 (4)	C11—C17—H17	120.5
C12—C11—C17	124.7 (4)	C17—N1—C21	119.5 (4)
C13—C12—C11	123.0 (4)	C26—C21—C22	117.3 (4)
C13—C12—N2	117.1 (4)	C26—C21—N1	124.1 (4)
C11—C12—N2	119.9 (4)	C22—C21—N1	118.5 (4)
O2—N2—O1	124.2 (4)	C23—C22—C21	121.9 (4)
O2—N2—C12	117.9 (4)	C23—C22—I2	120.0 (3)
O1—N2—C12	117.9 (3)	C21—C22—I2	118.1 (3)
C14—C13—C12	118.6 (4)	C24—C23—C22	120.3 (4)
C14—C13—H13	120.7	C24—C23—H23	119.8
C12—C13—H13	120.7	C22—C23—H23	119.8
C15—C14—C13	120.0 (4)	C23—C24—C25	118.6 (4)
C15—C14—H14	120.0	C23—C24—H24	120.7
C13—C14—H14	120.0	C25—C24—H24	120.7
C14—C15—C16	120.3 (4)	C26—C25—C24	121.2 (4)
C14—C15—H15	119.9	C26—C25—H25	119.4
C16—C15—H15	119.9	C24—C25—H25	119.4
C15—C16—C11	121.7 (4)	C25—C26—C21	120.7 (4)
C15—C16—H16	119.1	C25—C26—H26	119.6
C11—C16—H16	119.1	C21—C26—H26	119.6
N1—C17—C11	119.0 (4)

C16—C11—C12—C13	−1.6 (6)	C12—C11—C17—N1	157.0 (4)
C17—C11—C12—C13	173.1 (4)	C11—C17—N1—C21	177.9 (3)
C16—C11—C12—N2	176.2 (3)	C17—N1—C21—C26	32.7 (6)
C17—C11—C12—N2	−9.1 (6)	C17—N1—C21—C22	−150.8 (4)
C13—C12—N2—O2	152.0 (4)	C26—C21—C22—C23	−0.8 (6)
C11—C12—N2—O2	−26.0 (5)	N1—C21—C22—C23	−177.6 (4)
C13—C12—N2—O1	−26.6 (5)	C26—C21—C22—I2	180.0 (3)
C11—C12—N2—O1	155.5 (4)	N1—C21—C22—I2	3.2 (5)
C11—C12—C13—C14	1.4 (6)	C21—C22—C23—C24	0.9 (6)
N2—C12—C13—C14	−176.4 (3)	I2—C22—C23—C24	−180.0 (3)
C12—C13—C14—C15	0.7 (6)	C22—C23—C24—C25	−0.7 (6)
C13—C14—C15—C16	−2.6 (6)	C23—C24—C25—C26	0.4 (6)
C14—C15—C16—C11	2.4 (6)	C24—C25—C26—C21	−0.4 (6)
C12—C11—C16—C15	−0.3 (6)	C22—C21—C26—C25	0.6 (6)
C17—C11—C16—C15	−175.4 (4)	N1—C21—C26—C25	177.2 (4)
C16—C11—C17—N1	−28.4 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2	0.95	2.37	2.723 (5)	102

(II) 23-Nitrobenzylidene-2'-iodoaniline top

Crystal data top

C₁₃H₉IN₂O₂	F(000) = 680
M_r = 352.12	D_x = 1.878 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2685 reflections
a = 7.9059 (3) Å	θ = 3.0–27.5°
b = 22.6230 (7) Å	µ = 2.57 mm⁻¹
c = 7.6095 (2) Å	T = 120 K
β = 113.755 (1)°	Block, brown
V = 1245.69 (7) Å³	0.25 × 0.20 × 0.10 mm
Z = 4

Data collection top

Kappa-CCD diffractometer	2685 independent reflections
Radiation source: fine-focus sealed X-ray tube	2327 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −10→10
T_min = 0.599, T_max = 0.774	k = −29→29
11972 measured reflections	l = −9→8

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0409P)² + 3.5014P] where P = (F_o² + 2F_c²)/3
2685 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 1.44 e Å⁻³
0 restraints	Δρ_min = −1.25 e Å⁻³

Crystal data top

C₁₃H₉IN₂O₂	V = 1245.69 (7) Å³
M_r = 352.12	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9059 (3) Å	µ = 2.57 mm⁻¹
b = 22.6230 (7) Å	T = 120 K
c = 7.6095 (2) Å	0.25 × 0.20 × 0.10 mm
β = 113.755 (1)°

Data collection top

Kappa-CCD diffractometer	2685 independent reflections
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	2327 reflections with I > 2σ(I)
T_min = 0.599, T_max = 0.774	R_int = 0.079
11972 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.07	Δρ_max = 1.44 e Å⁻³
2685 reflections	Δρ_min = −1.25 e Å⁻³
163 parameters

Special details top

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	U_iso*/U_eq
C11	0.5484 (5)	0.01063 (19)	0.2873 (6)	0.0236 (8)
C12	0.3789 (5)	0.00064 (18)	0.1340 (5)	0.0219 (8)
C13	0.2860 (6)	0.04895 (19)	0.0278 (6)	0.0255 (9)
N3	0.1084 (5)	0.03905 (18)	−0.1350 (5)	0.0306 (8)
O1	0.0250 (5)	0.08222 (17)	−0.2266 (5)	0.0436 (8)
O2	0.0521 (4)	−0.01176 (15)	−0.1725 (5)	0.0395 (8)
C14	0.3554 (6)	0.1058 (2)	0.0637 (6)	0.0305 (9)
C15	0.5242 (6)	0.1148 (2)	0.2144 (6)	0.0304 (9)
C16	0.6188 (6)	0.06763 (19)	0.3272 (6)	0.0265 (9)
C17	0.6492 (6)	−0.03938 (19)	0.4085 (6)	0.0253 (9)
N1	0.6045 (5)	−0.09230 (16)	0.3553 (5)	0.0247 (7)
C21	0.6988 (6)	−0.13860 (19)	0.4799 (6)	0.0241 (8)
C22	0.5991 (6)	−0.18951 (19)	0.4774 (6)	0.0242 (9)
I2	0.31945 (4)	−0.195323 (13)	0.29295 (4)	0.03139 (13)
C23	0.6797 (6)	−0.2358 (2)	0.6032 (6)	0.0289 (9)
C24	0.8636 (6)	−0.2324 (2)	0.7303 (6)	0.0322 (10)
C25	0.9664 (6)	−0.1832 (2)	0.7282 (7)	0.0305 (10)
C26	0.8854 (6)	−0.1366 (2)	0.6043 (6)	0.0268 (9)
H12	0.3291	−0.0381	0.1037	0.026*
H14	0.2885	0.1379	−0.0136	0.037*
H15	0.5754	0.1535	0.2409	0.036*
H16	0.7331	0.0743	0.4331	0.032*
H17	0.7491	−0.0318	0.5282	0.030*
H23	0.6089	−0.2698	0.6022	0.035*
H24	0.9185	−0.2636	0.8183	0.039*
H25	1.0935	−0.1812	0.8122	0.037*
H26	0.9575	−0.1031	0.6040	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0154 (19)	0.039 (2)	0.020 (2)	0.0045 (16)	0.0100 (17)	−0.0015 (16)
C12	0.0150 (19)	0.034 (2)	0.0178 (19)	0.0003 (15)	0.0077 (16)	−0.0041 (15)
C13	0.0150 (19)	0.042 (2)	0.016 (2)	0.0047 (16)	0.0037 (16)	−0.0010 (16)
N3	0.0166 (18)	0.053 (2)	0.0217 (19)	0.0070 (16)	0.0068 (15)	−0.0018 (16)
O1	0.0270 (18)	0.056 (2)	0.038 (2)	0.0077 (16)	0.0027 (16)	0.0103 (16)
O2	0.0254 (17)	0.050 (2)	0.0318 (18)	0.0017 (14)	−0.0001 (15)	−0.0109 (15)
C14	0.026 (2)	0.040 (2)	0.025 (2)	0.0076 (18)	0.0105 (19)	0.0020 (18)
C15	0.027 (2)	0.036 (2)	0.029 (2)	−0.0027 (18)	0.0115 (19)	−0.0036 (18)
C16	0.0145 (19)	0.044 (2)	0.022 (2)	−0.0017 (16)	0.0076 (17)	−0.0051 (17)
C17	0.016 (2)	0.043 (2)	0.018 (2)	0.0015 (16)	0.0075 (17)	−0.0023 (16)
N1	0.0183 (17)	0.037 (2)	0.0203 (17)	0.0022 (14)	0.0090 (15)	0.0005 (14)
C21	0.018 (2)	0.037 (2)	0.018 (2)	0.0021 (16)	0.0075 (17)	−0.0024 (16)
C22	0.0093 (18)	0.049 (3)	0.017 (2)	0.0013 (15)	0.0089 (17)	−0.0027 (16)
I2	0.01648 (18)	0.0446 (2)	0.0287 (2)	−0.00213 (11)	0.00455 (14)	−0.00359 (11)
C23	0.024 (2)	0.039 (2)	0.026 (2)	0.0012 (17)	0.0132 (19)	0.0009 (17)
C24	0.028 (2)	0.043 (3)	0.026 (2)	0.0101 (19)	0.011 (2)	0.0057 (18)
C25	0.018 (2)	0.045 (3)	0.026 (2)	0.0061 (17)	0.006 (2)	0.0002 (18)
C26	0.0154 (19)	0.041 (2)	0.023 (2)	0.0006 (17)	0.0068 (17)	−0.0034 (17)

Geometric parameters (Å, º) top

C11—C16	1.389 (6)	C17—N1	1.268 (6)
C11—C12	1.396 (6)	C17—H17	0.9500
C11—C17	1.474 (6)	N1—C21	1.408 (5)
C12—C13	1.382 (6)	C21—C22	1.391 (6)
C12—H12	0.9500	C21—C26	1.396 (6)
C13—C14	1.381 (6)	C22—C23	1.388 (6)
C13—N3	1.468 (5)	C22—I2	2.092 (4)
N3—O2	1.224 (5)	C23—C24	1.386 (6)
N3—O1	1.226 (5)	C23—H23	0.9500
C14—C15	1.380 (6)	C24—C25	1.382 (7)
C14—H14	0.9500	C24—H24	0.9500
C15—C16	1.385 (6)	C25—C26	1.386 (6)
C15—H15	0.9500	C25—H25	0.9500
C16—H16	0.9500	C26—H26	0.9500

C16—C11—C12	119.9 (4)	N1—C17—H17	119.5
C16—C11—C17	120.5 (4)	C11—C17—H17	119.5
C12—C11—C17	119.6 (4)	C17—N1—C21	118.9 (4)
C13—C12—C11	117.8 (4)	C22—C21—C26	118.3 (4)
C13—C12—H12	121.1	C22—C21—N1	117.6 (4)
C11—C12—H12	121.1	C26—C21—N1	124.1 (4)
C14—C13—C12	123.0 (4)	C23—C22—C21	121.0 (4)
C14—C13—N3	118.5 (4)	C23—C22—I2	118.9 (3)
C12—C13—N3	118.4 (4)	C21—C22—I2	120.1 (3)
O2—N3—O1	123.6 (4)	C24—C23—C22	120.0 (4)
O2—N3—C13	118.3 (4)	C24—C23—H23	120.0
O1—N3—C13	118.1 (4)	C22—C23—H23	120.0
C15—C14—C13	118.5 (4)	C25—C24—C23	119.6 (4)
C15—C14—H14	120.8	C25—C24—H24	120.2
C13—C14—H14	120.8	C23—C24—H24	120.2
C14—C15—C16	120.0 (4)	C24—C25—C26	120.5 (4)
C14—C15—H15	120.0	C24—C25—H25	119.8
C16—C15—H15	120.0	C26—C25—H25	119.8
C15—C16—C11	120.8 (4)	C25—C26—C21	120.6 (4)
C15—C16—H16	119.6	C25—C26—H26	119.7
C11—C16—H16	119.6	C21—C26—H26	119.7
N1—C17—C11	120.9 (4)

C16—C11—C12—C13	−0.6 (6)	C12—C11—C17—N1	14.0 (6)
C17—C11—C12—C13	177.9 (3)	C11—C17—N1—C21	−176.9 (3)
C11—C12—C13—C14	1.7 (6)	C17—N1—C21—C22	146.4 (4)
C11—C12—C13—N3	179.4 (3)	C17—N1—C21—C26	−34.0 (6)
C14—C13—N3—O2	176.2 (4)	C26—C21—C22—C23	3.8 (6)
C12—C13—N3—O2	−1.7 (6)	N1—C21—C22—C23	−176.6 (4)
C14—C13—N3—O1	−3.4 (6)	C26—C21—C22—I2	−179.6 (3)
C12—C13—N3—O1	178.7 (4)	N1—C21—C22—I2	0.0 (5)
C12—C13—C14—C15	−1.0 (6)	C21—C22—C23—C24	−1.7 (6)
N3—C13—C14—C15	−178.7 (4)	I2—C22—C23—C24	−178.4 (3)
C13—C14—C15—C16	−0.8 (6)	C22—C23—C24—C25	−1.2 (6)
C14—C15—C16—C11	1.9 (6)	C23—C24—C25—C26	2.0 (7)
C12—C11—C16—C15	−1.1 (6)	C24—C25—C26—C21	0.1 (6)
C17—C11—C16—C15	−179.6 (4)	C22—C21—C26—C25	−3.0 (6)
C16—C11—C17—N1	−167.5 (4)	N1—C21—C26—C25	177.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱ	0.95	2.60	3.538 (6)	172
C26—H26···O2ⁱ	0.95	2.59	3.286 (6)	131

Symmetry code: (i) x+1, y, z+1.

(III) 4-Nitrobenzylidene-2'-iodoanilinb-Nitrobenzylidene-2'-iodoanilin top

Crystal data top

C₁₃H₉IN₂O₂	F(000) = 680
M_r = 352.12	D_x = 1.877 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2829 reflections
a = 10.1401 (7) Å	θ = 3.0–27.5°
b = 13.7454 (10) Å	µ = 2.57 mm⁻¹
c = 9.7829 (6) Å	T = 120 K
β = 113.961 (4)°	Block, yellow
V = 1246.03 (15) Å³	0.15 × 0.08 × 0.07 mm
Z = 4

Data collection top

Kappa-CCD diffractometer	2829 independent reflections
Radiation source: fine-focus sealed X-ray tube	1954 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −11→13
T_min = 0.641, T_max = 0.836	k = −16→17
7436 measured reflections	l = −12→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0352P)²] where P = (F_o² + 2F_c²)/3
2829 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.97 e Å⁻³
0 restraints	Δρ_min = −1.43 e Å⁻³

Crystal data top

C₁₃H₉IN₂O₂	V = 1246.03 (15) Å³
M_r = 352.12	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1401 (7) Å	µ = 2.57 mm⁻¹
b = 13.7454 (10) Å	T = 120 K
c = 9.7829 (6) Å	0.15 × 0.08 × 0.07 mm
β = 113.961 (4)°

Data collection top

Kappa-CCD diffractometer	2829 independent reflections
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	1954 reflections with I > 2σ(I)
T_min = 0.641, T_max = 0.836	R_int = 0.077
7436 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.01	Δρ_max = 0.97 e Å⁻³
2829 reflections	Δρ_min = −1.43 e Å⁻³
163 parameters

Special details top

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	U_iso*/U_eq
C11	0.3128 (4)	0.4375 (3)	0.3258 (5)	0.0204 (9)
C12	0.3493 (4)	0.4817 (3)	0.2182 (5)	0.0208 (9)
C13	0.3804 (4)	0.5804 (3)	0.2266 (5)	0.0198 (9)
C14	0.3716 (4)	0.6320 (3)	0.3438 (5)	0.0211 (10)
N4	0.4031 (4)	0.7373 (2)	0.3532 (4)	0.0231 (9)
O1	0.3712 (4)	0.7858 (2)	0.4390 (4)	0.0355 (8)
O2	0.4591 (4)	0.7706 (2)	0.2739 (4)	0.0297 (8)
C15	0.3348 (4)	0.5904 (3)	0.4515 (5)	0.0202 (9)
C16	0.3041 (4)	0.4926 (3)	0.4413 (5)	0.0208 (9)
C17	0.2754 (4)	0.3332 (3)	0.3088 (5)	0.0198 (9)
N1	0.2389 (4)	0.2895 (3)	0.4031 (4)	0.0213 (8)
C21	0.1994 (5)	0.1901 (3)	0.3750 (5)	0.0220 (10)
C22	0.0769 (5)	0.1582 (3)	0.3934 (5)	0.0226 (10)
I2	−0.04322 (3)	0.256503 (19)	0.46080 (3)	0.02695 (13)
C23	0.0321 (5)	0.0621 (3)	0.3637 (5)	0.0288 (11)
C24	0.1110 (5)	−0.0027 (3)	0.3221 (5)	0.0291 (11)
C25	0.2366 (6)	0.0272 (3)	0.3083 (5)	0.0293 (11)
C26	0.2788 (5)	0.1236 (3)	0.3336 (5)	0.0239 (10)
H12	0.3529	0.4441	0.1384	0.025*
H13	0.4067	0.6113	0.1544	0.024*
H15	0.3306	0.6284	0.5308	0.024*
H16	0.2769	0.4624	0.5133	0.025*
H17	0.2786	0.2981	0.2265	0.024*
H23	−0.0536	0.0414	0.3723	0.035*
H24	0.0803	−0.0685	0.3025	0.035*
H25	0.2927	−0.0183	0.2818	0.035*
H26	0.3632	0.1443	0.3223	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.019 (2)	0.021 (2)	0.020 (2)	0.0001 (18)	0.007 (2)	0.0007 (18)
C12	0.022 (2)	0.020 (2)	0.021 (2)	0.0018 (18)	0.010 (2)	−0.0023 (18)
C13	0.020 (2)	0.018 (2)	0.023 (2)	0.0027 (18)	0.011 (2)	0.0034 (17)
C14	0.020 (2)	0.015 (2)	0.026 (3)	0.0012 (18)	0.007 (2)	0.0017 (17)
N4	0.026 (2)	0.0197 (18)	0.022 (2)	−0.0022 (16)	0.0075 (18)	0.0016 (15)
O1	0.057 (2)	0.0227 (15)	0.032 (2)	0.0009 (16)	0.0235 (19)	−0.0061 (15)
O2	0.038 (2)	0.0237 (16)	0.032 (2)	−0.0077 (14)	0.0189 (17)	0.0013 (13)
C15	0.022 (2)	0.019 (2)	0.021 (2)	−0.0011 (18)	0.010 (2)	−0.0035 (17)
C16	0.024 (2)	0.022 (2)	0.020 (2)	0.0025 (18)	0.012 (2)	0.0052 (17)
C17	0.021 (2)	0.021 (2)	0.018 (3)	0.0029 (18)	0.008 (2)	−0.0013 (17)
N1	0.024 (2)	0.0209 (17)	0.020 (2)	−0.0018 (16)	0.0092 (18)	−0.0018 (16)
C21	0.030 (2)	0.019 (2)	0.016 (2)	0.0017 (19)	0.008 (2)	0.0033 (17)
C22	0.027 (2)	0.023 (2)	0.016 (2)	0.0010 (19)	0.008 (2)	0.0018 (17)
I2	0.0242 (2)	0.0311 (2)	0.0273 (2)	0.00061 (13)	0.01225 (15)	0.00046 (13)
C23	0.034 (3)	0.026 (2)	0.023 (3)	−0.010 (2)	0.008 (2)	0.001 (2)
C24	0.047 (3)	0.015 (2)	0.025 (3)	−0.011 (2)	0.015 (2)	−0.0002 (18)
C25	0.053 (3)	0.018 (2)	0.022 (3)	0.006 (2)	0.019 (2)	0.0029 (18)
C26	0.030 (3)	0.023 (2)	0.023 (3)	0.001 (2)	0.015 (2)	0.0038 (18)

Geometric parameters (Å, º) top

C11—C12	1.389 (6)	C17—N1	1.275 (5)
C11—C16	1.391 (6)	C17—H17	0.9500
C11—C17	1.475 (5)	N1—C21	1.419 (5)
C12—C13	1.388 (5)	C21—C26	1.383 (6)
C12—H12	0.9500	C21—C22	1.396 (6)
C13—C14	1.381 (6)	C22—C23	1.390 (5)
C13—H13	0.9500	C22—I2	2.097 (4)
C14—C15	1.377 (6)	C23—C24	1.365 (6)
C14—N4	1.477 (5)	C23—H23	0.9500
N4—O1	1.214 (5)	C24—C25	1.396 (7)
N4—O2	1.221 (5)	C24—H24	0.9500
C15—C16	1.375 (5)	C25—C26	1.383 (6)
C15—H15	0.9500	C25—H25	0.9500
C16—H16	0.9500	C26—H26	0.9500

C12—C11—C16	120.1 (4)	N1—C17—H17	119.6
C12—C11—C17	118.3 (4)	C11—C17—H17	119.6
C16—C11—C17	121.5 (4)	C17—N1—C21	117.1 (3)
C13—C12—C11	120.4 (4)	C26—C21—C22	119.0 (4)
C13—C12—H12	119.8	C26—C21—N1	122.8 (4)
C11—C12—H12	119.8	C22—C21—N1	118.2 (4)
C14—C13—C12	117.5 (4)	C23—C22—C21	120.3 (4)
C14—C13—H13	121.3	C23—C22—I2	119.7 (3)
C12—C13—H13	121.3	C21—C22—I2	120.0 (3)
C15—C14—C13	123.4 (4)	C24—C23—C22	120.1 (4)
C15—C14—N4	118.5 (4)	C24—C23—H23	120.0
C13—C14—N4	118.0 (4)	C22—C23—H23	120.0
O1—N4—O2	123.9 (3)	C23—C24—C25	120.4 (4)
O1—N4—C14	118.0 (4)	C23—C24—H24	119.8
O2—N4—C14	118.2 (4)	C25—C24—H24	119.8
C16—C15—C14	118.3 (4)	C26—C25—C24	119.5 (4)
C16—C15—H15	120.9	C26—C25—H25	120.3
C14—C15—H15	120.9	C24—C25—H25	120.3
C15—C16—C11	120.3 (4)	C21—C26—C25	120.8 (4)
C15—C16—H16	119.9	C21—C26—H26	119.6
C11—C16—H16	119.9	C25—C26—H26	119.6
N1—C17—C11	120.9 (4)

C16—C11—C12—C13	1.4 (6)	C16—C11—C17—N1	−2.6 (6)
C17—C11—C12—C13	177.8 (4)	C11—C17—N1—C21	177.7 (4)
C11—C12—C13—C14	−0.8 (6)	C17—N1—C21—C26	45.8 (6)
C12—C13—C14—C15	0.4 (6)	C17—N1—C21—C22	−135.6 (4)
C12—C13—C14—N4	−179.4 (4)	C26—C21—C22—C23	−2.9 (6)
C15—C14—N4—O1	−12.6 (6)	N1—C21—C22—C23	178.5 (4)
C13—C14—N4—O1	167.2 (4)	C26—C21—C22—I2	178.6 (3)
C15—C14—N4—O2	167.7 (4)	N1—C21—C22—I2	0.0 (5)
C13—C14—N4—O2	−12.5 (6)	C21—C22—C23—C24	2.6 (6)
C13—C14—C15—C16	−0.5 (6)	I2—C22—C23—C24	−178.9 (3)
N4—C14—C15—C16	179.3 (4)	C22—C23—C24—C25	−0.4 (7)
C14—C15—C16—C11	1.0 (6)	C23—C24—C25—C26	−1.6 (7)
C12—C11—C16—C15	−1.5 (6)	C22—C21—C26—C25	1.0 (7)
C17—C11—C16—C15	−177.7 (4)	N1—C21—C26—C25	179.6 (4)
C12—C11—C17—N1	−178.9 (4)	C24—C25—C26—C21	1.2 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1ⁱ	0.95	2.44	3.331 (6)	156

Symmetry code: (i) x, −y+3/2, z−1/2.

(IV) 2-Nitrobenzylidene-3'-iodoaniline top

Crystal data top

C₁₃H₉IN₂O₂	F(000) = 680
M_r = 352.12	D_x = 1.869 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2731 reflections
a = 12.0589 (6) Å	θ = 3.4–27.5°
b = 4.5562 (2) Å	µ = 2.55 mm⁻¹
c = 22.9725 (14) Å	T = 120 K
β = 97.3970 (18)°	Needle, orange
V = 1251.67 (11) Å³	0.50 × 0.10 × 0.05 mm
Z = 4

Data collection top

Kappa-CCD diffractometer	2731 independent reflections
Radiation source: fine-focus sealed X-ray tube	2033 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.4°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −13→15
T_min = 0.763, T_max = 0.876	k = −4→5
5744 measured reflections	l = −23→29

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0136P)²] where P = (F_o² + 2F_c²)/3
2731 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.97 e Å⁻³
0 restraints	Δρ_min = −0.97 e Å⁻³

Crystal data top

C₁₃H₉IN₂O₂	V = 1251.67 (11) Å³
M_r = 352.12	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0589 (6) Å	µ = 2.55 mm⁻¹
b = 4.5562 (2) Å	T = 120 K
c = 22.9725 (14) Å	0.50 × 0.10 × 0.05 mm
β = 97.3970 (18)°

Data collection top

Kappa-CCD diffractometer	2731 independent reflections
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	2033 reflections with I > 2σ(I)
T_min = 0.763, T_max = 0.876	R_int = 0.039
5744 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 0.95	Δρ_max = 0.97 e Å⁻³
2731 reflections	Δρ_min = −0.97 e Å⁻³
163 parameters

Special details top

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	U_iso*/U_eq
C11	0.6141 (3)	0.5913 (7)	0.15035 (15)	0.0171 (8)
C12	0.6753 (3)	0.6226 (7)	0.20558 (15)	0.0158 (8)
N2	0.6352 (2)	0.8102 (6)	0.25019 (13)	0.0192 (7)
O1	0.6624 (2)	0.7453 (4)	0.30196 (11)	0.0291 (6)
O2	0.5780 (2)	1.0253 (5)	0.23403 (10)	0.0220 (6)
C13	0.7764 (3)	0.4824 (7)	0.22192 (16)	0.0217 (8)
C14	0.8190 (3)	0.3044 (7)	0.18141 (16)	0.0235 (9)
C15	0.7609 (3)	0.2675 (6)	0.12631 (16)	0.0224 (8)
C16	0.6588 (3)	0.4066 (7)	0.11093 (15)	0.0190 (8)
C17	0.5029 (3)	0.7235 (6)	0.13353 (15)	0.0152 (7)
N1	0.4675 (2)	0.7679 (5)	0.07945 (12)	0.0176 (6)
C21	0.3562 (3)	0.8764 (7)	0.06603 (14)	0.0158 (8)
C22	0.2698 (3)	0.7731 (6)	0.09515 (14)	0.0169 (8)
C23	0.1632 (3)	0.8858 (7)	0.08035 (14)	0.0174 (8)
I3	0.032644 (19)	0.72327 (4)	0.123537 (10)	0.02323 (10)
C24	0.1415 (3)	1.0965 (7)	0.03711 (14)	0.0190 (8)
C25	0.2280 (3)	1.1945 (7)	0.00809 (15)	0.0215 (8)
C26	0.3349 (3)	1.0838 (7)	0.02186 (14)	0.0201 (8)
H13	0.8156	0.5079	0.2602	0.026*
H14	0.8886	0.2075	0.1916	0.028*
H15	0.7908	0.1460	0.0986	0.027*
H16	0.6188	0.3754	0.0730	0.023*
H17	0.4577	0.7755	0.1629	0.018*
H22	0.2836	0.6274	0.1248	0.020*
H24	0.0682	1.1729	0.0275	0.023*
H25	0.2138	1.3396	−0.0216	0.026*
H26	0.3935	1.1497	0.0012	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.016 (2)	0.0140 (17)	0.022 (2)	−0.0014 (13)	0.0049 (17)	0.0028 (14)
C12	0.015 (2)	0.0138 (16)	0.019 (2)	−0.0041 (14)	0.0034 (16)	0.0004 (14)
N2	0.0167 (17)	0.0192 (15)	0.0221 (18)	−0.0033 (12)	0.0038 (14)	0.0000 (13)
O1	0.0377 (18)	0.0310 (15)	0.0171 (14)	0.0032 (11)	−0.0023 (13)	0.0013 (11)
O2	0.0219 (15)	0.0167 (13)	0.0275 (15)	0.0013 (10)	0.0030 (12)	0.0011 (10)
C13	0.019 (2)	0.0192 (18)	0.026 (2)	−0.0044 (15)	0.0009 (18)	0.0057 (15)
C14	0.014 (2)	0.0208 (19)	0.036 (2)	0.0044 (14)	0.0040 (18)	0.0051 (16)
C15	0.023 (2)	0.021 (2)	0.026 (2)	0.0027 (15)	0.0123 (17)	−0.0003 (15)
C16	0.017 (2)	0.0207 (18)	0.020 (2)	−0.0015 (14)	0.0047 (17)	0.0024 (15)
C17	0.0133 (18)	0.0158 (18)	0.017 (2)	−0.0025 (13)	0.0049 (15)	−0.0002 (14)
N1	0.0135 (16)	0.0210 (16)	0.0184 (17)	−0.0007 (11)	0.0028 (13)	0.0010 (12)
C21	0.013 (2)	0.0184 (17)	0.016 (2)	0.0006 (14)	0.0004 (16)	−0.0035 (14)
C22	0.017 (2)	0.0186 (18)	0.0148 (19)	0.0000 (14)	0.0024 (15)	−0.0025 (14)
C23	0.017 (2)	0.0173 (17)	0.019 (2)	−0.0034 (14)	0.0059 (16)	−0.0015 (14)
I3	0.01532 (15)	0.02940 (15)	0.02554 (16)	−0.00045 (10)	0.00486 (11)	0.00069 (11)
C24	0.017 (2)	0.0191 (18)	0.020 (2)	0.0034 (14)	−0.0019 (17)	−0.0052 (15)
C25	0.022 (2)	0.0221 (19)	0.018 (2)	−0.0002 (15)	−0.0034 (17)	0.0042 (15)
C26	0.021 (2)	0.0246 (19)	0.015 (2)	−0.0029 (15)	0.0031 (17)	−0.0001 (15)

Geometric parameters (Å, º) top

C11—C12	1.391 (4)	C17—N1	1.277 (4)
C11—C16	1.394 (4)	C17—H17	0.9500
C11—C17	1.475 (5)	N1—C21	1.426 (4)
C12—C13	1.384 (4)	C21—C26	1.386 (4)
C12—N2	1.464 (4)	C21—C22	1.391 (4)
N2—O2	1.228 (3)	C22—C23	1.385 (4)
N2—O1	1.228 (3)	C22—H22	0.9500
C13—C14	1.383 (5)	C23—C24	1.382 (4)
C13—H13	0.9500	C23—I3	2.101 (3)
C14—C15	1.376 (5)	C24—C25	1.382 (5)
C14—H14	0.9500	C24—H24	0.9500
C15—C16	1.390 (5)	C25—C26	1.383 (5)
C15—H15	0.9500	C25—H25	0.9500
C16—H16	0.9500	C26—H26	0.9500

C12—C11—C16	116.8 (3)	N1—C17—H17	120.0
C12—C11—C17	123.7 (3)	C11—C17—H17	120.0
C16—C11—C17	119.4 (3)	C17—N1—C21	116.9 (3)
C13—C12—C11	123.1 (3)	C26—C21—C22	120.2 (3)
C13—C12—N2	116.0 (3)	C26—C21—N1	118.4 (3)
C11—C12—N2	120.9 (3)	C22—C21—N1	121.4 (3)
O2—N2—O1	123.7 (3)	C23—C22—C21	119.0 (3)
O2—N2—C12	118.5 (3)	C23—C22—H22	120.5
O1—N2—C12	117.8 (3)	C21—C22—H22	120.5
C14—C13—C12	118.6 (3)	C24—C23—C22	121.2 (3)
C14—C13—H13	120.7	C24—C23—I3	120.0 (3)
C12—C13—H13	120.7	C22—C23—I3	118.8 (2)
C15—C14—C13	120.1 (3)	C23—C24—C25	119.1 (3)
C15—C14—H14	120.0	C23—C24—H24	120.4
C13—C14—H14	120.0	C25—C24—H24	120.4
C14—C15—C16	120.5 (3)	C24—C25—C26	120.7 (3)
C14—C15—H15	119.7	C24—C25—H25	119.6
C16—C15—H15	119.7	C26—C25—H25	119.6
C15—C16—C11	120.9 (3)	C25—C26—C21	119.7 (3)
C15—C16—H16	119.5	C25—C26—H26	120.1
C11—C16—H16	119.5	C21—C26—H26	120.1
N1—C17—C11	119.9 (3)

C16—C11—C12—C13	0.5 (5)	C12—C11—C17—N1	157.6 (3)
C17—C11—C12—C13	175.8 (3)	C16—C11—C17—N1	−27.2 (4)
C16—C11—C12—N2	−179.6 (3)	C11—C17—N1—C21	175.6 (3)
C17—C11—C12—N2	−4.3 (5)	C17—N1—C21—C26	141.3 (3)
C13—C12—N2—O2	149.6 (3)	C17—N1—C21—C22	−40.3 (4)
C11—C12—N2—O2	−30.3 (4)	C26—C21—C22—C23	−1.6 (5)
C13—C12—N2—O1	−29.2 (4)	N1—C21—C22—C23	−179.9 (3)
C11—C12—N2—O1	150.9 (3)	C21—C22—C23—C24	0.4 (5)
C11—C12—C13—C14	0.5 (5)	C21—C22—C23—I3	178.9 (2)
N2—C12—C13—C14	−179.4 (3)	C22—C23—C24—C25	0.3 (5)
C12—C13—C14—C15	−0.5 (5)	I3—C23—C24—C25	−178.2 (2)
C13—C14—C15—C16	−0.4 (5)	C23—C24—C25—C26	0.1 (5)
C14—C15—C16—C11	1.4 (5)	C24—C25—C26—C21	−1.2 (5)
C12—C11—C16—C15	−1.4 (5)	C22—C21—C26—C25	2.0 (5)
C17—C11—C16—C15	−177.0 (3)	N1—C21—C26—C25	−179.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O1ⁱ	0.95	2.45	3.397 (4)	174

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

(V) 3-Nitrobenzylidene-3'-iodoaniline top

Crystal data top

C₁₃H₉IN₂O₂	F(000) = 680
M_r = 352.12	D_x = 1.941 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2752 reflections
a = 7.4741 (3) Å	θ = 3.1–27.5°
b = 11.3487 (4) Å	µ = 2.65 mm⁻¹
c = 14.2039 (6) Å	T = 120 K
V = 1204.79 (8) Å³	Needle, colourless
Z = 4	0.20 × 0.06 × 0.06 mm

Data collection top

Kappa-CCD diffractometer	2752 independent reflections
Radiation source: fine-focus sealed X-ray tube	2275 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.117
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −9→8
T_min = 0.665, T_max = 0.853	k = −13→14
8100 measured reflections	l = −18→16

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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0287P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2752 reflections	Δρ_max = 2.03 e Å⁻³
163 parameters	Δρ_min = −1.52 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1141 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (4)

Crystal data top

C₁₃H₉IN₂O₂	V = 1204.79 (8) Å³
M_r = 352.12	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.4741 (3) Å	µ = 2.65 mm⁻¹
b = 11.3487 (4) Å	T = 120 K
c = 14.2039 (6) Å	0.20 × 0.06 × 0.06 mm

Data collection top

Kappa-CCD diffractometer	2752 independent reflections
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	2275 reflections with I > 2σ(I)
T_min = 0.665, T_max = 0.853	R_int = 0.117
8100 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.100	Δρ_max = 2.03 e Å⁻³
S = 1.00	Δρ_min = −1.52 e Å⁻³
2752 reflections	Absolute structure: Flack (1983), 1141 Friedel pairs
163 parameters	Absolute structure parameter: −0.03 (4)
0 restraints

Special details top

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	U_iso*/U_eq
C11	0.1483 (8)	0.3185 (6)	0.4039 (4)	0.0206 (14)
C12	0.0866 (9)	0.2944 (5)	0.3130 (4)	0.0206 (14)
C13	0.1019 (9)	0.3808 (6)	0.2450 (4)	0.0203 (14)
N3	0.0297 (7)	0.3563 (4)	0.1502 (3)	0.0219 (12)
O1	0.0202 (7)	0.4369 (4)	0.0931 (3)	0.0263 (10)
O2	−0.0187 (7)	0.2542 (4)	0.1339 (3)	0.0257 (10)
C14	0.1760 (9)	0.4901 (6)	0.2619 (4)	0.0201 (13)
C15	0.2401 (8)	0.5135 (6)	0.3518 (4)	0.0201 (14)
C16	0.2259 (8)	0.4302 (5)	0.4216 (5)	0.0201 (13)
N1	0.1764 (7)	0.2530 (5)	0.5636 (4)	0.0227 (12)
C17	0.1304 (9)	0.2309 (6)	0.4777 (4)	0.0196 (14)
C21	0.1603 (8)	0.1620 (6)	0.6312 (4)	0.0192 (13)
C22	0.1072 (8)	0.1950 (5)	0.7213 (4)	0.0196 (14)
C23	0.1002 (9)	0.1120 (5)	0.7933 (4)	0.0200 (14)
I3	0.01514 (5)	0.16623 (3)	0.92775 (2)	0.02301 (14)
C24	0.1481 (8)	−0.0040 (6)	0.7771 (4)	0.0196 (13)
C25	0.2046 (9)	−0.0352 (6)	0.6867 (5)	0.0231 (15)
C26	0.2125 (9)	0.0461 (6)	0.6139 (5)	0.0225 (16)
H12	0.0352	0.2201	0.2983	0.025*
H14	0.1830	0.5477	0.2135	0.024*
H15	0.2940	0.5875	0.3651	0.024*
H16	0.2689	0.4478	0.4829	0.024*
H17	0.0838	0.1554	0.4624	0.024*
H22	0.0756	0.2746	0.7337	0.023*
H24	0.1429	−0.0609	0.8261	0.024*
H25	0.2385	−0.1144	0.6747	0.028*
H26	0.2529	0.0231	0.5532	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.020 (3)	0.026 (4)	0.016 (3)	0.004 (3)	0.000 (2)	−0.003 (3)
C12	0.021 (4)	0.016 (3)	0.025 (3)	−0.002 (2)	0.002 (3)	−0.002 (3)
C13	0.023 (4)	0.027 (4)	0.011 (3)	0.005 (3)	0.002 (2)	−0.006 (3)
N3	0.019 (3)	0.028 (3)	0.019 (3)	0.003 (2)	0.006 (2)	0.001 (2)
O1	0.030 (3)	0.028 (2)	0.021 (2)	0.003 (2)	0.001 (2)	0.0095 (18)
O2	0.035 (3)	0.024 (2)	0.018 (2)	0.001 (2)	−0.004 (2)	−0.0041 (18)
C14	0.021 (3)	0.018 (3)	0.022 (3)	0.000 (3)	0.001 (2)	0.002 (3)
C15	0.023 (4)	0.016 (4)	0.022 (3)	0.001 (3)	0.000 (3)	−0.008 (3)
C16	0.016 (3)	0.022 (3)	0.022 (3)	0.001 (2)	0.003 (3)	−0.007 (3)
N1	0.030 (3)	0.028 (3)	0.010 (3)	0.002 (2)	0.001 (2)	−0.003 (2)
C17	0.025 (4)	0.019 (3)	0.015 (3)	0.001 (3)	0.001 (3)	−0.002 (3)
C21	0.019 (3)	0.025 (3)	0.014 (3)	−0.001 (3)	−0.004 (2)	0.003 (3)
C22	0.021 (3)	0.021 (4)	0.017 (3)	−0.002 (2)	0.000 (3)	−0.006 (3)
C23	0.017 (3)	0.024 (4)	0.018 (3)	−0.002 (2)	−0.003 (3)	−0.003 (3)
I3	0.0302 (2)	0.0252 (2)	0.01354 (19)	−0.00083 (18)	0.00137 (17)	0.00167 (16)
C24	0.023 (3)	0.019 (3)	0.017 (3)	−0.001 (3)	−0.005 (2)	0.005 (3)
C25	0.019 (4)	0.021 (4)	0.029 (4)	0.004 (2)	0.003 (3)	−0.001 (3)
C26	0.022 (4)	0.026 (4)	0.019 (4)	−0.001 (3)	−0.002 (3)	−0.009 (3)

Geometric parameters (Å, º) top

C11—C12	1.399 (8)	N1—C17	1.293 (8)
C11—C16	1.416 (9)	N1—C21	1.416 (8)
C11—C17	1.450 (9)	C17—H17	0.9500
C12—C13	1.381 (9)	C21—C22	1.391 (8)
C12—H12	0.9500	C21—C26	1.394 (9)
C13—C14	1.379 (10)	C22—C23	1.392 (9)
C13—N3	1.477 (7)	C22—H22	0.9500
N3—O1	1.224 (6)	C23—C24	1.384 (9)
N3—O2	1.236 (6)	C23—I3	2.105 (6)
C14—C15	1.389 (9)	C24—C25	1.398 (9)
C14—H14	0.9500	C24—H24	0.9500
C15—C16	1.374 (9)	C25—C26	1.387 (9)
C15—H15	0.9500	C25—H25	0.9500
C16—H16	0.9500	C26—H26	0.9500

C12—C11—C16	118.3 (6)	N1—C17—C11	121.6 (6)
C12—C11—C17	120.2 (6)	N1—C17—H17	119.2
C16—C11—C17	121.5 (6)	C11—C17—H17	119.2
C13—C12—C11	118.6 (6)	C22—C21—C26	119.8 (6)
C13—C12—H12	120.7	C22—C21—N1	116.8 (6)
C11—C12—H12	120.7	C26—C21—N1	123.1 (5)
C14—C13—C12	123.3 (6)	C21—C22—C23	120.3 (6)
C14—C13—N3	118.4 (5)	C21—C22—H22	119.9
C12—C13—N3	118.3 (6)	C23—C22—H22	119.9
O1—N3—O2	124.0 (5)	C24—C23—C22	120.8 (6)
O1—N3—C13	118.9 (5)	C24—C23—I3	120.5 (4)
O2—N3—C13	117.0 (5)	C22—C23—I3	118.7 (4)
C13—C14—C15	118.1 (6)	C23—C24—C25	118.1 (6)
C13—C14—H14	120.9	C23—C24—H24	120.9
C15—C14—H14	120.9	C25—C24—H24	120.9
C16—C15—C14	120.3 (6)	C26—C25—C24	122.0 (6)
C16—C15—H15	119.9	C26—C25—H25	119.0
C14—C15—H15	119.9	C24—C25—H25	119.0
C15—C16—C11	121.3 (6)	C25—C26—C21	119.0 (6)
C15—C16—H16	119.3	C25—C26—H26	120.5
C11—C16—H16	119.3	C21—C26—H26	120.5
C17—N1—C21	118.4 (5)

C16—C11—C12—C13	−0.8 (9)	C12—C11—C17—N1	−175.8 (6)
C17—C11—C12—C13	178.5 (6)	C16—C11—C17—N1	3.5 (9)
C11—C12—C13—C14	0.3 (10)	C17—N1—C21—C22	−143.4 (6)
C11—C12—C13—N3	−177.5 (6)	C17—N1—C21—C26	43.4 (8)
C14—C13—N3—O1	−7.7 (9)	C26—C21—C22—C23	−2.2 (9)
C12—C13—N3—O1	170.2 (6)	N1—C21—C22—C23	−175.6 (5)
C14—C13—N3—O2	172.6 (6)	C21—C22—C23—C24	0.9 (9)
C12—C13—N3—O2	−9.4 (9)	C21—C22—C23—I3	−179.1 (5)
C12—C13—C14—C15	0.7 (10)	C22—C23—C24—C25	0.3 (9)
N3—C13—C14—C15	178.6 (6)	I3—C23—C24—C25	−179.7 (5)
C13—C14—C15—C16	−1.3 (10)	C23—C24—C25—C26	−0.4 (10)
C14—C15—C16—C11	0.8 (9)	C24—C25—C26—C21	−0.9 (10)
C12—C11—C16—C15	0.3 (9)	C22—C21—C26—C25	2.1 (9)
C17—C11—C16—C15	−179.0 (6)	N1—C21—C26—C25	175.1 (6)
C21—N1—C17—C11	−178.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1ⁱ	0.95	2.58	3.437 (8)	151

Symmetry code: (i) −x+1/2, −y+1, z+1/2.

(VI) 4-Nitrobenzylidene-3'-iodoaniline top

Crystal data top

C₁₃H₉IN₂O₂	F(000) = 680
M_r = 352.12	D_x = 1.936 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2627 reflections
a = 7.1179 (2) Å	θ = 3.0–27.5°
b = 12.3905 (3) Å	µ = 2.65 mm⁻¹
c = 13.6983 (5) Å	T = 120 K
V = 1208.11 (6) Å³	Block, yellow
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection top

Kappa-CCD diffractometer	2627 independent reflections
Radiation source: fine-focus sealed X-ray tube	2453 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −8→7
T_min = 0.607, T_max = 0.768	k = −16→13
6019 measured reflections	l = −17→15

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)] = 0.029	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0355P)² + 0.6144P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
2627 reflections	Δρ_max = 0.69 e Å⁻³
163 parameters	Δρ_min = −1.08 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1023 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.07 (3)

Crystal data top

C₁₃H₉IN₂O₂	V = 1208.11 (6) Å³
M_r = 352.12	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.1179 (2) Å	µ = 2.65 mm⁻¹
b = 12.3905 (3) Å	T = 120 K
c = 13.6983 (5) Å	0.20 × 0.10 × 0.10 mm

Data collection top

Kappa-CCD diffractometer	2627 independent reflections
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	2453 reflections with I > 2σ(I)
T_min = 0.607, T_max = 0.768	R_int = 0.033
6019 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.078	Δρ_max = 0.69 e Å⁻³
S = 1.11	Δρ_min = −1.08 e Å⁻³
2627 reflections	Absolute structure: Flack (1983), 1023 Friedel pairs
163 parameters	Absolute structure parameter: −0.07 (3)
0 restraints

Special details top

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	U_iso*/U_eq
C11	0.1058 (6)	0.6892 (3)	−0.0842 (4)	0.0183 (9)
C12	0.0835 (7)	0.5780 (4)	−0.0902 (4)	0.0221 (10)
C13	0.1047 (7)	0.5256 (4)	−0.1794 (3)	0.0193 (10)
C14	0.1514 (7)	0.5869 (4)	−0.2599 (3)	0.0213 (10)
N4	0.1802 (6)	0.5322 (3)	−0.3538 (3)	0.0224 (9)
O1	0.2153 (5)	0.5879 (3)	−0.4250 (2)	0.0305 (8)
O2	0.1716 (5)	0.4336 (3)	−0.3558 (3)	0.0274 (8)
C15	0.1697 (6)	0.6977 (4)	−0.2564 (3)	0.0174 (9)
C16	0.1484 (7)	0.7489 (4)	−0.1685 (3)	0.0173 (10)
C17	0.0867 (7)	0.7419 (4)	0.0111 (3)	0.0188 (10)
N1	0.1404 (6)	0.8394 (3)	0.0241 (3)	0.0193 (8)
C21	0.1264 (7)	0.8837 (4)	0.1186 (3)	0.0186 (10)
C22	0.1690 (6)	0.8247 (4)	0.2022 (3)	0.0164 (9)
C23	0.1630 (7)	0.8739 (4)	0.2933 (3)	0.0188 (10)
I3	0.21739 (5)	0.78146 (2)	0.41821 (2)	0.02409 (11)
C24	0.1226 (7)	0.9828 (4)	0.3026 (3)	0.0208 (10)
C25	0.0822 (7)	1.0415 (4)	0.2182 (4)	0.0220 (11)
C26	0.0851 (7)	0.9936 (4)	0.1276 (3)	0.0204 (10)
H12	0.0538	0.5376	−0.0333	0.027*
H13	0.0875	0.4498	−0.1848	0.023*
H15	0.1965	0.7378	−0.3139	0.021*
H16	0.1624	0.8250	−0.1645	0.021*
H17	0.0335	0.7030	0.0641	0.023*
H22	0.2023	0.7507	0.1969	0.020*
H24	0.1225	1.0167	0.3648	0.025*
H25	0.0521	1.1160	0.2235	0.026*
H26	0.0590	1.0354	0.0710	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.018 (2)	0.022 (2)	0.015 (2)	−0.0007 (16)	0.0003 (19)	0.000 (2)
C12	0.028 (3)	0.021 (2)	0.017 (2)	0.0017 (18)	−0.003 (2)	0.001 (2)
C13	0.019 (3)	0.018 (2)	0.020 (2)	0.0000 (18)	0.0034 (18)	0.0001 (19)
C14	0.021 (2)	0.025 (2)	0.018 (2)	0.0043 (19)	0.0037 (19)	−0.002 (2)
N4	0.029 (3)	0.024 (2)	0.0143 (18)	0.0020 (18)	−0.0041 (16)	−0.0027 (17)
O1	0.045 (2)	0.0295 (18)	0.0164 (16)	0.0032 (16)	0.0082 (19)	−0.0010 (15)
O2	0.033 (2)	0.0232 (19)	0.0263 (19)	−0.0025 (15)	0.0009 (15)	−0.0070 (15)
C15	0.013 (2)	0.022 (2)	0.016 (2)	−0.0035 (16)	−0.0009 (17)	0.0011 (19)
C16	0.018 (2)	0.019 (2)	0.016 (2)	0.0028 (17)	−0.0002 (18)	−0.0020 (16)
C17	0.012 (2)	0.027 (3)	0.017 (2)	0.0023 (18)	0.0000 (17)	0.0008 (19)
N1	0.021 (2)	0.023 (2)	0.0138 (18)	0.0021 (18)	−0.0066 (16)	−0.0024 (17)
C21	0.018 (3)	0.021 (2)	0.016 (2)	−0.0063 (19)	0.0054 (18)	−0.0015 (18)
C22	0.014 (3)	0.020 (2)	0.015 (2)	−0.0035 (17)	−0.0050 (17)	0.0012 (18)
C23	0.013 (2)	0.024 (2)	0.019 (2)	−0.0023 (18)	0.0076 (18)	0.0009 (19)
I3	0.03200 (19)	0.02618 (17)	0.01408 (14)	−0.00145 (13)	−0.00185 (12)	0.00168 (13)
C24	0.022 (3)	0.024 (3)	0.016 (2)	−0.006 (2)	0.0038 (19)	0.000 (2)
C25	0.017 (3)	0.021 (3)	0.028 (3)	−0.0005 (18)	−0.0011 (19)	−0.005 (2)
C26	0.017 (3)	0.027 (3)	0.017 (2)	0.0046 (19)	−0.0011 (18)	0.003 (2)

Geometric parameters (Å, º) top

C11—C12	1.390 (6)	C17—N1	1.280 (6)
C11—C16	1.405 (6)	C17—H17	0.9500
C11—C17	1.466 (7)	N1—C21	1.408 (6)
C12—C13	1.393 (7)	C21—C22	1.392 (6)
C12—H12	0.9500	C21—C26	1.399 (7)
C13—C14	1.379 (7)	C22—C23	1.390 (6)
C13—H13	0.9500	C22—H22	0.9500
C14—C15	1.380 (6)	C23—C24	1.386 (7)
C14—N4	1.468 (6)	C23—I3	2.095 (5)
N4—O1	1.222 (5)	C24—C25	1.395 (7)
N4—O2	1.224 (5)	C24—H24	0.9500
C15—C16	1.369 (6)	C25—C26	1.376 (7)
C15—H15	0.9500	C25—H25	0.9500
C16—H16	0.9500	C26—H26	0.9500

C12—C11—C16	119.9 (5)	N1—C17—H17	119.4
C12—C11—C17	118.9 (4)	C11—C17—H17	119.4
C16—C11—C17	121.2 (4)	C17—N1—C21	118.3 (4)
C11—C12—C13	120.1 (5)	C22—C21—C26	118.9 (4)
C11—C12—H12	120.0	C22—C21—N1	122.4 (4)
C13—C12—H12	120.0	C26—C21—N1	118.4 (4)
C14—C13—C12	118.1 (4)	C23—C22—C21	120.1 (4)
C14—C13—H13	120.9	C23—C22—H22	119.9
C12—C13—H13	120.9	C21—C22—H22	119.9
C13—C14—C15	122.9 (4)	C24—C23—C22	121.0 (4)
C13—C14—N4	118.6 (4)	C24—C23—I3	119.8 (3)
C15—C14—N4	118.5 (4)	C22—C23—I3	119.2 (3)
O1—N4—O2	123.8 (4)	C23—C24—C25	118.3 (4)
O1—N4—C14	117.9 (4)	C23—C24—H24	120.8
O2—N4—C14	118.3 (4)	C25—C24—H24	120.8
C16—C15—C14	118.7 (4)	C26—C25—C24	121.3 (5)
C16—C15—H15	120.6	C26—C25—H25	119.4
C14—C15—H15	120.6	C24—C25—H25	119.4
C15—C16—C11	120.2 (4)	C25—C26—C21	120.2 (5)
C15—C16—H16	119.9	C25—C26—H26	119.9
C11—C16—H16	119.9	C21—C26—H26	119.9
N1—C17—C11	121.1 (4)

C16—C11—C12—C13	0.5 (7)	C16—C11—C17—N1	−12.7 (7)
C17—C11—C12—C13	−178.7 (4)	C11—C17—N1—C21	−177.0 (4)
C11—C12—C13—C14	1.2 (7)	C17—N1—C21—C22	39.9 (7)
C12—C13—C14—C15	−2.9 (7)	C17—N1—C21—C26	−146.2 (5)
C12—C13—C14—N4	178.0 (4)	C26—C21—C22—C23	2.6 (7)
C13—C14—N4—O1	177.6 (4)	N1—C21—C22—C23	176.4 (4)
C15—C14—N4—O1	−1.4 (6)	C21—C22—C23—C24	−2.8 (7)
C13—C14—N4—O2	−3.9 (7)	C21—C22—C23—I3	177.6 (3)
C15—C14—N4—O2	177.0 (4)	C22—C23—C24—C25	2.0 (7)
C13—C14—C15—C16	2.9 (7)	I3—C23—C24—C25	−178.3 (4)
N4—C14—C15—C16	−178.1 (4)	C23—C24—C25—C26	−1.1 (7)
C14—C15—C16—C11	−1.0 (7)	C24—C25—C26—C21	1.0 (7)
C12—C11—C16—C15	−0.6 (7)	C22—C21—C26—C25	−1.7 (7)
C17—C11—C16—C15	178.6 (4)	N1—C21—C26—C25	−175.8 (4)
C12—C11—C17—N1	166.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O2ⁱ	0.95	2.56	3.487 (6)	166

Symmetry code: (i) −x+1/2, −y+1, z+1/2.

(VII) 2-Nitrobenzylidene-4'-iodoaniline top

Crystal data top

C₁₃H₉IN₂O₂	F(000) = 2720
M_r = 352.12	D_x = 1.892 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5417 reflections
a = 52.458 (2) Å	θ = 3.0–27.5°
b = 4.3786 (2) Å	µ = 2.59 mm⁻¹
c = 23.5973 (13) Å	T = 120 K
β = 114.185 (2)°	Needle, yellow
V = 4944.4 (4) Å³	0.15 × 0.04 × 0.03 mm
Z = 16

Data collection top

Kappa-CCD diffractometer	5417 independent reflections
Radiation source: fine-focus sealed X-ray tube	2368 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.128
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −67→67
T_min = 0.893, T_max = 0.928	k = −5→5
13621 measured reflections	l = −30→30

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 0.84	w = 1/[σ²(F_o²) + (0.010P)²] where P = (F_o² + 2F_c²)/3
5417 reflections	(Δ/σ)_max = 0.001
325 parameters	Δρ_max = 1.23 e Å⁻³
0 restraints	Δρ_min = −0.95 e Å⁻³

Crystal data top

C₁₃H₉IN₂O₂	V = 4944.4 (4) Å³
M_r = 352.12	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 52.458 (2) Å	µ = 2.59 mm⁻¹
b = 4.3786 (2) Å	T = 120 K
c = 23.5973 (13) Å	0.15 × 0.04 × 0.03 mm
β = 114.185 (2)°

Data collection top

Kappa-CCD diffractometer	5417 independent reflections
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	2368 reflections with I > 2σ(I)
T_min = 0.893, T_max = 0.928	R_int = 0.128
13621 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 0.84	Δρ_max = 1.23 e Å⁻³
5417 reflections	Δρ_min = −0.95 e Å⁻³
325 parameters

Special details top

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	U_iso*/U_eq
C11	0.6581 (2)	0.4591 (18)	0.6623 (4)	0.0212 (16)
C12	0.62831 (18)	0.4333 (17)	0.6364 (4)	0.015 (2)
N12	0.61259 (18)	0.5912 (18)	0.6671 (4)	0.030 (2)
O11	0.58921 (14)	0.4827 (15)	0.6575 (3)	0.045 (2)
O12	0.62260 (14)	0.8170 (14)	0.6990 (3)	0.0344 (18)
C13	0.61316 (19)	0.2709 (17)	0.5827 (4)	0.0229 (17)
C14	0.6270 (2)	0.1304 (19)	0.5518 (4)	0.0267 (18)
C15	0.6554 (2)	0.158 (2)	0.5731 (4)	0.027 (3)
C16	0.6710 (2)	0.3127 (19)	0.6283 (4)	0.027 (2)
N11	0.69907 (16)	0.7074 (15)	0.7307 (3)	0.0200 (19)
C17	0.6750 (2)	0.6059 (17)	0.7208 (4)	0.020 (2)
C21	0.71695 (19)	0.8209 (19)	0.7895 (4)	0.020 (2)
C22	0.71752 (19)	0.7169 (18)	0.8461 (4)	0.0240 (18)
C23	0.73712 (19)	0.8219 (18)	0.9015 (4)	0.0240 (18)
C24	0.75704 (18)	1.0343 (18)	0.9016 (4)	0.0213 (16)
I14	0.788251 (14)	1.17904 (13)	0.98646 (3)	0.02528 (19)
C25	0.75727 (19)	1.1372 (17)	0.8463 (4)	0.0217 (18)
C26	0.73734 (19)	1.0306 (17)	0.7906 (4)	0.0217 (18)
C31	0.5153 (2)	0.1427 (17)	0.3750 (4)	0.0212 (16)
C32	0.5133 (2)	−0.0572 (15)	0.4199 (4)	0.026 (2)
N32	0.53848 (19)	−0.1868 (18)	0.4691 (4)	0.030 (2)
O31	0.56104 (14)	−0.0600 (14)	0.4827 (3)	0.0395 (19)
O32	0.53502 (14)	−0.4234 (15)	0.4940 (3)	0.0393 (19)
C33	0.48773 (19)	−0.1240 (19)	0.4208 (4)	0.0229 (17)
C34	0.4639 (2)	0.0029 (18)	0.3781 (4)	0.0267 (18)
C35	0.4653 (2)	0.2019 (19)	0.3333 (4)	0.030 (3)
C36	0.4911 (2)	0.2696 (19)	0.3318 (4)	0.031 (3)
N21	0.54423 (15)	0.4832 (16)	0.3477 (3)	0.026 (2)
C37	0.54208 (19)	0.2274 (19)	0.3718 (4)	0.023 (2)
C41	0.5708 (2)	0.5630 (18)	0.3498 (5)	0.022 (2)
C42	0.5953 (2)	0.5115 (17)	0.4007 (4)	0.027 (3)
C43	0.62121 (19)	0.6112 (17)	0.4047 (4)	0.0229 (17)
C44	0.62129 (19)	0.7613 (18)	0.3524 (4)	0.0213 (16)
I24	0.659632 (13)	0.93115 (13)	0.35624 (3)	0.02751 (19)
C45	0.59738 (19)	0.8203 (18)	0.3007 (4)	0.0229 (17)
C46	0.57176 (19)	0.7254 (16)	0.2991 (4)	0.0217 (7)
H13	0.5934	0.2572	0.5676	0.028*
H14	0.6169	0.0138	0.5155	0.032*
H15	0.6646	0.0702	0.5499	0.033*
H16	0.6908	0.3186	0.6430	0.032*
H17	0.6680	0.6261	0.7519	0.024*
H22	0.7041	0.5712	0.8461	0.029*
H23	0.7372	0.7509	0.9395	0.029*
H25	0.7710	1.2796	0.8466	0.026*
H26	0.7375	1.1004	0.7526	0.026*
H33	0.4868	−0.2589	0.4514	0.028*
H34	0.4464	−0.0445	0.3787	0.032*
H35	0.4486	0.2920	0.3038	0.036*
H36	0.4919	0.4035	0.3009	0.037*
H37	0.5576	0.0923	0.3876	0.027*
H42	0.5945	0.4029	0.4348	0.033*
H43	0.6379	0.5790	0.4409	0.028*
H45	0.5983	0.9249	0.2663	0.028*
H46	0.5550	0.7700	0.2640	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.023 (5)	0.011 (4)	0.031 (5)	−0.007 (3)	0.012 (4)	−0.005 (3)
C12	0.012 (6)	0.013 (5)	0.017 (6)	0.004 (4)	0.003 (5)	0.008 (4)
N12	0.019 (6)	0.032 (5)	0.036 (6)	0.006 (5)	0.008 (5)	−0.007 (4)
O11	0.023 (5)	0.057 (5)	0.063 (6)	−0.009 (4)	0.024 (5)	−0.018 (4)
O12	0.040 (5)	0.026 (4)	0.041 (5)	0.000 (4)	0.020 (4)	−0.013 (3)
C13	0.021 (4)	0.026 (4)	0.022 (4)	−0.010 (3)	0.009 (4)	−0.008 (3)
C14	0.017 (5)	0.030 (4)	0.032 (5)	−0.007 (3)	0.008 (4)	−0.009 (3)
C15	0.031 (7)	0.028 (6)	0.030 (7)	0.011 (5)	0.019 (6)	0.012 (5)
C16	0.017 (6)	0.037 (6)	0.031 (7)	0.001 (5)	0.015 (6)	0.004 (5)
N11	0.017 (5)	0.022 (4)	0.023 (5)	−0.010 (4)	0.011 (4)	−0.010 (4)
C17	0.030 (7)	0.006 (5)	0.035 (7)	0.003 (5)	0.025 (6)	−0.002 (4)
C21	0.020 (6)	0.020 (5)	0.018 (6)	0.009 (5)	0.007 (5)	−0.003 (5)
C22	0.023 (5)	0.022 (4)	0.035 (5)	0.004 (4)	0.019 (4)	0.000 (4)
C23	0.023 (5)	0.022 (4)	0.035 (5)	0.004 (4)	0.019 (4)	0.000 (4)
C24	0.015 (4)	0.023 (4)	0.026 (4)	0.000 (3)	0.009 (4)	0.002 (3)
I14	0.0207 (4)	0.0275 (4)	0.0275 (4)	−0.0037 (3)	0.0097 (3)	−0.0021 (3)
C25	0.027 (5)	0.015 (4)	0.035 (5)	−0.005 (3)	0.025 (4)	−0.005 (3)
C26	0.027 (5)	0.015 (4)	0.035 (5)	−0.005 (3)	0.025 (4)	−0.005 (3)
C31	0.023 (5)	0.011 (4)	0.031 (5)	−0.007 (3)	0.012 (4)	−0.005 (3)
C32	0.024 (7)	0.012 (5)	0.037 (7)	−0.008 (5)	0.008 (6)	−0.011 (5)
N32	0.041 (7)	0.025 (5)	0.029 (6)	0.004 (5)	0.019 (5)	−0.007 (4)
O31	0.015 (4)	0.047 (4)	0.048 (5)	−0.014 (4)	0.004 (4)	−0.004 (4)
O32	0.044 (5)	0.038 (4)	0.035 (5)	−0.006 (4)	0.015 (4)	0.004 (4)
C33	0.021 (4)	0.026 (4)	0.022 (4)	−0.010 (3)	0.009 (4)	−0.008 (3)
C34	0.017 (5)	0.030 (4)	0.032 (5)	−0.007 (3)	0.008 (4)	−0.009 (3)
C35	0.024 (7)	0.032 (6)	0.029 (7)	0.012 (5)	0.006 (6)	−0.006 (5)
C36	0.029 (7)	0.028 (6)	0.043 (7)	0.004 (5)	0.023 (6)	0.002 (5)
N21	0.016 (5)	0.048 (6)	0.021 (5)	0.006 (4)	0.013 (4)	0.002 (4)
C37	0.023 (6)	0.022 (6)	0.020 (6)	−0.011 (5)	0.006 (5)	−0.011 (5)
C41	0.016 (6)	0.013 (5)	0.044 (7)	−0.002 (5)	0.019 (6)	−0.011 (5)
C42	0.043 (8)	0.018 (6)	0.022 (6)	−0.012 (5)	0.015 (6)	0.007 (5)
C43	0.020 (4)	0.024 (4)	0.028 (4)	−0.003 (3)	0.013 (4)	0.006 (3)
C44	0.015 (4)	0.023 (4)	0.026 (4)	0.000 (3)	0.009 (4)	0.002 (3)
I24	0.0193 (4)	0.0281 (4)	0.0370 (5)	−0.0003 (3)	0.0134 (4)	0.0056 (3)
C45	0.020 (4)	0.024 (4)	0.028 (4)	−0.003 (3)	0.013 (4)	0.006 (3)
C46	0.0270 (2)	0.0155 (17)	0.0345 (4)	−0.0053 (4)	0.0248 (15)	−0.0054 (2)

Geometric parameters (Å, º) top

C11—C16	1.402 (10)	C31—C36	1.379 (12)
C11—C12	1.429 (11)	C31—C32	1.411 (10)
C11—C17	1.450 (11)	C31—C37	1.484 (11)
C12—C13	1.385 (10)	C32—C33	1.383 (11)
C12—N12	1.473 (10)	C32—N32	1.469 (11)
N12—O12	1.223 (8)	N32—O31	1.225 (9)
N12—O11	1.247 (9)	N32—O32	1.240 (8)
C13—C14	1.367 (10)	C33—C34	1.362 (11)
C13—H13	0.9500	C33—H33	0.9500
C14—C15	1.369 (11)	C34—C35	1.392 (11)
C14—H14	0.9500	C34—H34	0.9500
C15—C16	1.397 (11)	C35—C36	1.402 (11)
C15—H15	0.9500	C35—H35	0.9500
C16—H16	0.9500	C36—H36	0.9500
N11—C17	1.266 (10)	N21—C37	1.282 (9)
N11—C21	1.409 (10)	N21—C41	1.419 (10)
C17—H17	0.9500	C37—H37	0.9500
C21—C22	1.400 (10)	C41—C42	1.370 (12)
C21—C26	1.402 (11)	C41—C46	1.409 (10)
C22—C23	1.369 (11)	C42—C43	1.395 (11)
C22—H22	0.9500	C42—H42	0.9500
C23—C24	1.397 (11)	C43—C44	1.400 (10)
C23—H23	0.9500	C43—H43	0.9500
C24—C25	1.386 (10)	C44—C45	1.369 (11)
C24—I14	2.099 (9)	C44—I24	2.111 (8)
C25—C26	1.383 (11)	C45—C46	1.393 (10)
C25—H25	0.9500	C45—H45	0.9500
C26—H26	0.9500	C46—H46	0.9500

C16—C11—C12	114.9 (8)	C36—C31—C32	118.4 (9)
C16—C11—C17	119.7 (9)	C36—C31—C37	117.9 (8)
C12—C11—C17	125.3 (8)	C32—C31—C37	123.8 (9)
C13—C12—C11	123.2 (8)	C33—C32—C31	121.0 (9)
C13—C12—N12	117.6 (8)	C33—C32—N32	118.0 (8)
C11—C12—N12	119.1 (8)	C31—C32—N32	121.0 (9)
O12—N12—O11	124.2 (8)	O31—N32—O32	124.6 (9)
O12—N12—C12	119.7 (8)	O31—N32—C32	119.4 (8)
O11—N12—C12	116.0 (8)	O32—N32—C32	116.0 (8)
C14—C13—C12	119.3 (9)	C34—C33—C32	120.2 (9)
C14—C13—H13	120.4	C34—C33—H33	119.9
C12—C13—H13	120.4	C32—C33—H33	119.9
C13—C14—C15	119.9 (9)	C33—C34—C35	120.1 (9)
C13—C14—H14	120.1	C33—C34—H34	119.9
C15—C14—H14	120.1	C35—C34—H34	119.9
C14—C15—C16	121.5 (8)	C34—C35—C36	120.1 (9)
C14—C15—H15	119.3	C34—C35—H35	120.0
C16—C15—H15	119.3	C36—C35—H35	120.0
C15—C16—C11	121.1 (9)	C31—C36—C35	120.3 (9)
C15—C16—H16	119.5	C31—C36—H36	119.9
C11—C16—H16	119.5	C35—C36—H36	119.9
C17—N11—C21	121.1 (7)	C37—N21—C41	117.6 (8)
N11—C17—C11	120.5 (8)	N21—C37—C31	119.8 (8)
N11—C17—H17	119.7	N21—C37—H37	120.1
C11—C17—H17	119.7	C31—C37—H37	120.1
C22—C21—C26	118.5 (9)	C42—C41—C46	118.7 (8)
C22—C21—N11	124.8 (8)	C42—C41—N21	122.9 (8)
C26—C21—N11	116.3 (8)	C46—C41—N21	118.1 (9)
C23—C22—C21	121.0 (9)	C41—C42—C43	123.0 (8)
C23—C22—H22	119.5	C41—C42—H42	118.5
C21—C22—H22	119.5	C43—C42—H42	118.5
C22—C23—C24	119.7 (9)	C42—C43—C44	116.2 (9)
C22—C23—H23	120.2	C42—C43—H43	121.9
C24—C23—H23	120.2	C44—C43—H43	121.9
C25—C24—C23	120.6 (9)	C45—C44—C43	122.8 (8)
C25—C24—I14	119.7 (6)	C45—C44—I24	118.7 (6)
C23—C24—I14	119.6 (6)	C43—C44—I24	118.3 (7)
C26—C25—C24	119.4 (8)	C44—C45—C46	119.3 (8)
C26—C25—H25	120.3	C44—C45—H45	120.4
C24—C25—H25	120.3	C46—C45—H45	120.4
C25—C26—C21	120.8 (8)	C45—C46—C41	119.8 (9)
C25—C26—H26	119.6	C45—C46—H46	120.1
C21—C26—H26	119.6	C41—C46—H46	120.1

C16—C11—C12—C13	1.4 (12)	C36—C31—C32—C33	−0.2 (12)
C17—C11—C12—C13	−174.9 (8)	C37—C31—C32—C33	179.2 (7)
C16—C11—C12—N12	−177.2 (7)	C36—C31—C32—N32	−176.7 (8)
C17—C11—C12—N12	6.4 (12)	C37—C31—C32—N32	2.6 (12)
C13—C12—N12—O12	−153.6 (8)	C33—C32—N32—O31	−155.7 (7)
C11—C12—N12—O12	25.1 (11)	C31—C32—N32—O31	20.9 (12)
C13—C12—N12—O11	25.5 (11)	C33—C32—N32—O32	24.6 (11)
C11—C12—N12—O11	−155.7 (8)	C31—C32—N32—O32	−158.7 (7)
C11—C12—C13—C14	−1.0 (13)	C31—C32—C33—C34	0.1 (12)
N12—C12—C13—C14	177.7 (7)	N32—C32—C33—C34	176.7 (7)
C12—C13—C14—C15	−1.7 (13)	C32—C33—C34—C35	−0.3 (13)
C13—C14—C15—C16	3.8 (14)	C33—C34—C35—C36	0.7 (13)
C14—C15—C16—C11	−3.3 (14)	C32—C31—C36—C35	0.5 (12)
C12—C11—C16—C15	0.7 (12)	C37—C31—C36—C35	−178.8 (7)
C17—C11—C16—C15	177.3 (8)	C34—C35—C36—C31	−0.8 (13)
C21—N11—C17—C11	−173.2 (7)	C41—N21—C37—C31	175.7 (7)
C16—C11—C17—N11	27.2 (12)	C36—C31—C37—N21	25.8 (12)
C12—C11—C17—N11	−156.6 (8)	C32—C31—C37—N21	−153.5 (8)
C17—N11—C21—C22	31.1 (13)	C37—N21—C41—C42	−40.7 (12)
C17—N11—C21—C26	−155.7 (8)	C37—N21—C41—C46	144.8 (7)
C26—C21—C22—C23	1.4 (12)	C46—C41—C42—C43	−0.4 (13)
N11—C21—C22—C23	174.5 (8)	N21—C41—C42—C43	−174.8 (7)
C21—C22—C23—C24	−0.6 (12)	C41—C42—C43—C44	−2.0 (12)
C22—C23—C24—C25	−0.6 (12)	C42—C43—C44—C45	2.6 (12)
C22—C23—C24—I14	−177.1 (6)	C42—C43—C44—I24	178.0 (5)
C23—C24—C25—C26	0.8 (12)	C43—C44—C45—C46	−0.8 (13)
I14—C24—C25—C26	177.3 (6)	I24—C44—C45—C46	−176.2 (5)
C24—C25—C26—C21	0.1 (12)	C44—C45—C46—C41	−1.8 (12)
C22—C21—C26—C25	−1.2 (12)	C42—C41—C46—C45	2.3 (12)
N11—C21—C26—C25	−174.9 (7)	N21—C41—C46—C45	177.0 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O31	0.95	2.46	3.140 (11)	129
C17—H17···O12	0.95	2.34	2.742 (13)	105
C37—H37···O31	0.95	2.28	2.700 (11)	106
C33—H33···O32ⁱ	0.95	2.47	3.370 (12)	158
C34—H34···O11ⁱⁱ	0.95	2.57	3.327 (12)	137

Symmetry codes: (i) −x+1, −y−1, −z+1; (ii) −x+1, −y, −z+1.

(VIII) 3-Nitrobenzylidene-4'-iodoaniline top

Crystal data top

C₁₃H₉IN₂O₂	Z = 4
M_r = 352.12	F(000) = 680
Triclinic, P1	D_x = 1.888 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2646 (1) Å	Cell parameters from 5602 reflections
b = 11.8251 (2) Å	θ = 3.0–27.5°
c = 15.0057 (3) Å	µ = 2.58 mm⁻¹
α = 103.2458 (6)°	T = 120 K
β = 98.3999 (7)°	Rod, yellow
γ = 91.6291 (10)°	0.28 × 0.10 × 0.08 mm
V = 1238.74 (4) Å³

Data collection top

Kappa-CCD diffractometer	5602 independent reflections
Radiation source: fine-focus sealed X-ray tube	4991 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.076
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −9→9
T_min = 0.587, T_max = 0.814	k = −15→15
18561 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0279P)² + 1.1231P] where P = (F_o² + 2F_c²)/3
5602 reflections	(Δ/σ)_max = 0.003
325 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −1.18 e Å⁻³

Crystal data top

C₁₃H₉IN₂O₂	γ = 91.6291 (10)°
M_r = 352.12	V = 1238.74 (4) Å³
Triclinic, P1	Z = 4
a = 7.2646 (1) Å	Mo Kα radiation
b = 11.8251 (2) Å	µ = 2.58 mm⁻¹
c = 15.0057 (3) Å	T = 120 K
α = 103.2458 (6)°	0.28 × 0.10 × 0.08 mm
β = 98.3999 (7)°

Data collection top

Kappa-CCD diffractometer	5602 independent reflections
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	4991 reflections with I > 2σ(I)
T_min = 0.587, T_max = 0.814	R_int = 0.076
18561 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.03	Δρ_max = 0.66 e Å⁻³
5602 reflections	Δρ_min = −1.18 e Å⁻³
325 parameters

Special details top

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	U_iso*/U_eq
C11	0.6823 (4)	0.6439 (2)	0.99745 (18)	0.0198 (5)
C12	0.6110 (4)	0.6440 (2)	0.90570 (18)	0.0204 (5)
C13	0.5536 (4)	0.7466 (2)	0.88612 (17)	0.0198 (5)
N13	0.4780 (3)	0.7468 (2)	0.78935 (16)	0.0238 (5)
O11	0.4903 (3)	0.6587 (2)	0.72897 (14)	0.0360 (5)
O12	0.4080 (3)	0.83443 (19)	0.77380 (14)	0.0330 (5)
C14	0.5657 (5)	0.8499 (3)	0.9522 (2)	0.0308 (7)
C15	0.6379 (5)	0.8487 (3)	1.0431 (2)	0.0365 (8)
C16	0.6943 (5)	0.7467 (3)	1.06558 (19)	0.0281 (6)
C17	0.7453 (4)	0.5351 (2)	1.01811 (18)	0.0231 (6)
N11	0.8182 (3)	0.5274 (2)	1.09800 (15)	0.0235 (5)
C21	0.8758 (4)	0.4184 (2)	1.11256 (18)	0.0194 (5)
C22	0.8685 (4)	0.3154 (2)	1.04452 (18)	0.0243 (6)
C23	0.9271 (4)	0.2140 (2)	1.06756 (18)	0.0239 (6)
C24	0.9964 (4)	0.2150 (2)	1.15893 (18)	0.0202 (5)
I14	1.08069 (3)	0.059298 (16)	1.192057 (13)	0.02772 (7)
C25	1.0091 (4)	0.3164 (2)	1.22782 (18)	0.0217 (5)
C26	0.9488 (4)	0.4172 (2)	1.20382 (17)	0.0193 (5)
C31	0.7847 (4)	0.3484 (2)	0.53796 (18)	0.0207 (5)
C32	0.7716 (4)	0.3626 (2)	0.63192 (18)	0.0198 (5)
C33	0.8156 (4)	0.2714 (2)	0.67220 (18)	0.0202 (5)
N33	0.7992 (4)	0.2841 (2)	0.77028 (16)	0.0256 (5)
O31	0.7165 (4)	0.36639 (19)	0.80744 (14)	0.0355 (5)
O32	0.8681 (4)	0.21277 (19)	0.81026 (14)	0.0364 (5)
C34	0.8711 (4)	0.1662 (2)	0.62420 (19)	0.0225 (6)
C35	0.8792 (4)	0.1532 (2)	0.5316 (2)	0.0240 (6)
C36	0.8351 (4)	0.2422 (2)	0.48808 (19)	0.0245 (6)
C37	0.7448 (4)	0.4418 (2)	0.49021 (18)	0.0243 (6)
N21	0.7448 (3)	0.5474 (2)	0.53254 (16)	0.0233 (5)
C41	0.7097 (4)	0.6326 (2)	0.48009 (17)	0.0181 (5)
C42	0.6697 (4)	0.7425 (2)	0.52793 (17)	0.0196 (5)
C43	0.6367 (4)	0.8315 (2)	0.48228 (17)	0.0191 (5)
C44	0.6455 (4)	0.8102 (2)	0.38829 (17)	0.0184 (5)
I24	0.60101 (3)	0.944128 (15)	0.317776 (11)	0.02271 (7)
C45	0.6860 (4)	0.7016 (2)	0.33966 (18)	0.0225 (6)
C46	0.7172 (4)	0.6141 (2)	0.38571 (19)	0.0241 (6)
H12	0.6025	0.5747	0.8580	0.024*
H14	0.5262	0.9196	0.9362	0.037*
H15	0.6486	0.9186	1.0903	0.044*
H16	0.7416	0.7469	1.1281	0.034*
H17	0.7308	0.4670	0.9691	0.028*
H22	0.8229	0.3147	0.9817	0.029*
H23	0.9199	0.1438	1.0209	0.029*
H25	1.0580	0.3170	1.2902	0.026*
H26	0.9573	0.4873	1.2507	0.023*
H32	0.7334	0.4331	0.6669	0.024*
H34	0.9024	0.1055	0.6544	0.027*
H35	0.9157	0.0820	0.4970	0.029*
H36	0.8391	0.2310	0.4237	0.029*
H37	0.7177	0.4223	0.4244	0.029*
H42	0.6650	0.7566	0.5925	0.023*
H43	0.6085	0.9061	0.5151	0.023*
H45	0.6921	0.6877	0.2753	0.027*
H46	0.7443	0.5396	0.3524	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0200 (12)	0.0192 (13)	0.0216 (12)	0.0032 (11)	0.0045 (10)	0.0070 (10)
C12	0.0215 (13)	0.0202 (13)	0.0194 (12)	0.0020 (11)	0.0033 (10)	0.0044 (10)
C13	0.0211 (12)	0.0224 (13)	0.0175 (12)	0.0019 (11)	0.0029 (10)	0.0081 (10)
N13	0.0216 (11)	0.0272 (13)	0.0231 (11)	−0.0001 (10)	0.0005 (9)	0.0093 (10)
O11	0.0466 (13)	0.0369 (13)	0.0203 (10)	0.0026 (11)	−0.0039 (9)	0.0035 (9)
O12	0.0351 (12)	0.0337 (12)	0.0348 (11)	0.0030 (10)	−0.0012 (9)	0.0217 (10)
C14	0.0437 (18)	0.0241 (15)	0.0268 (14)	0.0127 (14)	0.0071 (13)	0.0081 (12)
C15	0.063 (2)	0.0216 (15)	0.0225 (14)	0.0173 (16)	0.0031 (14)	0.0016 (11)
C16	0.0411 (17)	0.0268 (15)	0.0168 (12)	0.0084 (14)	0.0023 (12)	0.0065 (11)
C17	0.0317 (15)	0.0163 (13)	0.0213 (13)	0.0031 (12)	0.0043 (11)	0.0038 (10)
N11	0.0305 (12)	0.0196 (11)	0.0211 (11)	0.0061 (10)	0.0030 (9)	0.0063 (9)
C21	0.0204 (12)	0.0187 (13)	0.0204 (12)	0.0012 (11)	0.0043 (10)	0.0066 (10)
C22	0.0325 (15)	0.0216 (14)	0.0172 (12)	0.0047 (12)	−0.0031 (11)	0.0050 (10)
C23	0.0301 (14)	0.0182 (13)	0.0216 (13)	0.0030 (12)	0.0019 (11)	0.0022 (10)
C24	0.0180 (12)	0.0183 (13)	0.0272 (14)	0.0019 (11)	0.0027 (10)	0.0118 (11)
I14	0.03308 (12)	0.02066 (11)	0.03354 (12)	0.00455 (9)	0.00488 (9)	0.01465 (8)
C25	0.0256 (13)	0.0240 (14)	0.0158 (12)	0.0010 (12)	0.0026 (10)	0.0060 (10)
C26	0.0211 (12)	0.0195 (13)	0.0177 (12)	0.0002 (11)	0.0041 (10)	0.0043 (10)
C31	0.0182 (12)	0.0200 (13)	0.0217 (13)	−0.0017 (11)	−0.0031 (10)	0.0044 (10)
C32	0.0171 (12)	0.0170 (13)	0.0221 (12)	0.0001 (11)	−0.0022 (10)	0.0018 (10)
C33	0.0191 (12)	0.0200 (13)	0.0196 (12)	−0.0005 (11)	−0.0007 (10)	0.0035 (10)
N33	0.0350 (13)	0.0190 (12)	0.0203 (11)	−0.0014 (11)	−0.0022 (10)	0.0040 (9)
O31	0.0541 (14)	0.0295 (12)	0.0225 (10)	0.0109 (11)	0.0080 (10)	0.0031 (9)
O32	0.0579 (15)	0.0254 (11)	0.0265 (10)	0.0064 (11)	−0.0025 (10)	0.0122 (9)
C34	0.0224 (13)	0.0183 (13)	0.0259 (14)	0.0018 (11)	−0.0020 (11)	0.0071 (11)
C35	0.0177 (12)	0.0198 (14)	0.0323 (15)	0.0038 (11)	−0.0002 (11)	0.0039 (11)
C36	0.0254 (14)	0.0240 (14)	0.0203 (13)	−0.0006 (12)	−0.0005 (11)	0.0002 (11)
C37	0.0301 (15)	0.0217 (14)	0.0190 (12)	−0.0004 (12)	−0.0039 (11)	0.0057 (10)
N21	0.0272 (12)	0.0229 (12)	0.0229 (11)	0.0054 (10)	0.0071 (9)	0.0094 (9)
C41	0.0170 (12)	0.0184 (13)	0.0200 (12)	0.0020 (11)	0.0046 (10)	0.0056 (10)
C42	0.0224 (13)	0.0223 (13)	0.0144 (11)	0.0016 (11)	0.0040 (10)	0.0046 (10)
C43	0.0221 (12)	0.0169 (12)	0.0170 (12)	0.0006 (11)	0.0031 (10)	0.0013 (9)
C44	0.0175 (12)	0.0206 (13)	0.0178 (12)	−0.0018 (11)	0.0014 (10)	0.0069 (10)
I24	0.03147 (11)	0.01894 (11)	0.01908 (10)	0.00189 (8)	0.00408 (8)	0.00717 (7)
C45	0.0291 (14)	0.0231 (14)	0.0164 (12)	0.0021 (12)	0.0071 (11)	0.0047 (10)
C46	0.0332 (15)	0.0167 (13)	0.0234 (13)	0.0050 (12)	0.0103 (12)	0.0030 (10)

Geometric parameters (Å, º) top

C11—C16	1.389 (4)	C31—C36	1.396 (4)
C11—C12	1.399 (4)	C31—C32	1.399 (4)
C11—C17	1.461 (4)	C31—C37	1.462 (4)
C12—C13	1.374 (4)	C32—C33	1.375 (4)
C12—H12	0.9500	C32—H32	0.9500
C13—C14	1.377 (4)	C33—C34	1.389 (4)
C13—N13	1.476 (3)	C33—N33	1.468 (3)
N13—O12	1.222 (3)	N33—O32	1.221 (3)
N13—O11	1.229 (3)	N33—O31	1.225 (3)
C14—C15	1.393 (4)	C34—C35	1.372 (4)
C14—H14	0.9500	C34—H34	0.9500
C15—C16	1.381 (4)	C35—C36	1.382 (4)
C15—H15	0.9500	C35—H35	0.9500
C16—H16	0.9500	C36—H36	0.9500
C17—N11	1.262 (3)	C37—N21	1.265 (4)
C17—H17	0.9500	C37—H37	0.9500
N11—C21	1.420 (3)	N21—C41	1.421 (3)
C21—C22	1.393 (4)	C41—C46	1.392 (4)
C21—C26	1.398 (4)	C41—C42	1.393 (4)
C22—C23	1.383 (4)	C42—C43	1.391 (4)
C22—H22	0.9500	C42—H42	0.9500
C23—C24	1.387 (4)	C43—C44	1.386 (3)
C23—H23	0.9500	C43—H43	0.9500
C24—C25	1.383 (4)	C44—C45	1.387 (4)
C24—I14	2.100 (3)	C44—I24	2.105 (3)
C25—C26	1.386 (4)	C45—C46	1.376 (4)
C25—H25	0.9500	C45—H45	0.9500
C26—H26	0.9500	C46—H46	0.9500

C16—C11—C12	119.5 (2)	C36—C31—C32	119.3 (3)
C16—C11—C17	122.0 (2)	C36—C31—C37	119.0 (2)
C12—C11—C17	118.5 (2)	C32—C31—C37	121.7 (2)
C13—C12—C11	118.5 (2)	C33—C32—C31	118.0 (2)
C13—C12—H12	120.8	C33—C32—H32	121.0
C11—C12—H12	120.8	C31—C32—H32	121.0
C12—C13—C14	123.2 (2)	C32—C33—C34	123.3 (2)
C12—C13—N13	118.6 (2)	C32—C33—N33	118.7 (2)
C14—C13—N13	118.2 (2)	C34—C33—N33	118.0 (2)
O12—N13—O11	123.8 (2)	O32—N33—O31	123.7 (2)
O12—N13—C13	118.3 (2)	O32—N33—C33	118.6 (2)
O11—N13—C13	117.9 (2)	O31—N33—C33	117.7 (2)
C13—C14—C15	117.7 (3)	C35—C34—C33	117.7 (3)
C13—C14—H14	121.2	C35—C34—H34	121.2
C15—C14—H14	121.2	C33—C34—H34	121.2
C16—C15—C14	120.7 (3)	C34—C35—C36	121.0 (3)
C16—C15—H15	119.7	C34—C35—H35	119.5
C14—C15—H15	119.7	C36—C35—H35	119.5
C15—C16—C11	120.5 (3)	C35—C36—C31	120.5 (3)
C15—C16—H16	119.8	C35—C36—H36	119.7
C11—C16—H16	119.8	C31—C36—H36	119.7
N11—C17—C11	123.1 (2)	N21—C37—C31	122.9 (2)
N11—C17—H17	118.4	N21—C37—H37	118.5
C11—C17—H17	118.4	C31—C37—H37	118.5
C17—N11—C21	119.8 (2)	C37—N21—C41	118.9 (2)
C22—C21—C26	118.2 (2)	C46—C41—C42	118.6 (2)
C22—C21—N11	126.0 (2)	C46—C41—N21	124.4 (2)
C26—C21—N11	115.8 (2)	C42—C41—N21	116.9 (2)
C23—C22—C21	120.6 (2)	C43—C42—C41	120.7 (2)
C23—C22—H22	119.7	C43—C42—H42	119.6
C21—C22—H22	119.7	C41—C42—H42	119.6
C22—C23—C24	119.9 (2)	C44—C43—C42	119.2 (2)
C22—C23—H23	120.1	C44—C43—H43	120.4
C24—C23—H23	120.1	C42—C43—H43	120.4
C25—C24—C23	121.0 (2)	C43—C44—C45	120.9 (2)
C25—C24—I14	120.03 (19)	C43—C44—I24	120.04 (19)
C23—C24—I14	119.0 (2)	C45—C44—I24	119.07 (19)
C24—C25—C26	118.5 (2)	C46—C45—C44	119.3 (2)
C24—C25—H25	120.7	C46—C45—H45	120.4
C26—C25—H25	120.7	C44—C45—H45	120.4
C25—C26—C21	121.8 (2)	C45—C46—C41	121.3 (2)
C25—C26—H26	119.1	C45—C46—H46	119.3
C21—C26—H26	119.1	C41—C46—H46	119.3

C16—C11—C12—C13	−0.4 (4)	C36—C31—C32—C33	2.2 (4)
C17—C11—C12—C13	−179.3 (3)	C37—C31—C32—C33	−178.5 (3)
C11—C12—C13—C14	1.1 (4)	C31—C32—C33—C34	−0.4 (4)
C11—C12—C13—N13	−179.9 (2)	C31—C32—C33—N33	−178.9 (2)
C12—C13—N13—O12	172.0 (3)	C32—C33—N33—O32	−167.4 (3)
C14—C13—N13—O12	−9.0 (4)	C34—C33—N33—O32	14.0 (4)
C12—C13—N13—O11	−8.5 (4)	C32—C33—N33—O31	12.6 (4)
C14—C13—N13—O11	170.5 (3)	C34—C33—N33—O31	−166.0 (3)
C12—C13—C14—C15	−0.8 (5)	C32—C33—C34—C35	−1.0 (4)
N13—C13—C14—C15	−179.8 (3)	N33—C33—C34—C35	177.5 (2)
C13—C14—C15—C16	−0.3 (5)	C33—C34—C35—C36	0.5 (4)
C14—C15—C16—C11	0.9 (5)	C34—C35—C36—C31	1.3 (4)
C12—C11—C16—C15	−0.6 (5)	C32—C31—C36—C35	−2.7 (4)
C17—C11—C16—C15	178.3 (3)	C37—C31—C36—C35	178.1 (3)
C16—C11—C17—N11	−1.6 (4)	C36—C31—C37—N21	−161.5 (3)
C12—C11—C17—N11	177.2 (3)	C32—C31—C37—N21	19.2 (4)
C11—C17—N11—C21	179.9 (3)	C31—C37—N21—C41	178.2 (2)
C17—N11—C21—C22	3.4 (4)	C37—N21—C41—C46	−15.6 (4)
C17—N11—C21—C26	−177.8 (3)	C37—N21—C41—C42	166.1 (3)
C26—C21—C22—C23	1.9 (4)	C46—C41—C42—C43	0.4 (4)
N11—C21—C22—C23	−179.3 (3)	N21—C41—C42—C43	178.9 (2)
C21—C22—C23—C24	−1.0 (4)	C41—C42—C43—C44	−0.5 (4)
C22—C23—C24—C25	−0.4 (4)	C42—C43—C44—C45	0.2 (4)
C22—C23—C24—I14	179.1 (2)	C42—C43—C44—I24	−178.89 (19)
C23—C24—C25—C26	0.8 (4)	C43—C44—C45—C46	0.2 (4)
I14—C24—C25—C26	−178.75 (19)	I24—C44—C45—C46	179.3 (2)
C24—C25—C26—C21	0.2 (4)	C44—C45—C46—C41	−0.3 (4)
C22—C21—C26—C25	−1.5 (4)	C42—C41—C46—C45	0.0 (4)
N11—C21—C26—C25	179.6 (3)	N21—C41—C46—C45	−178.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O31	0.95	2.43	3.303 (3)	153
C37—H37···O11ⁱ	0.95	2.53	3.406 (3)	154

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

	(I)	(II)	(III)	(IV)
Crystal data
Chemical formula	C₁₃H₉IN₂O₂	C₁₃H₉IN₂O₂	C₁₃H₉IN₂O₂	C₁₃H₉IN₂O₂
M_r	352.12	352.12	352.12	352.12
Crystal system, space group	Monoclinic, P2₁/n	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Monoclinic, P2₁/c
Temperature (K)	120	120	120	120
a, b, c (Å)	8.0664 (4), 10.7191 (5), 14.5692 (9)	7.9059 (3), 22.6230 (7), 7.6095 (2)	10.1401 (7), 13.7454 (10), 9.7829 (6)	12.0589 (6), 4.5562 (2), 22.9725 (14)
α, β, γ (°)	90, 99.026 (2), 90	90, 113.755 (1), 90	90, 113.961 (4), 90	90, 97.3970 (18), 90
V (Å³)	1244.12 (11)	1245.69 (7)	1246.03 (15)	1251.67 (11)
Z	4	4	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	2.57	2.57	2.57	2.55
Crystal size (mm)	0.17 × 0.04 × 0.02	0.25 × 0.20 × 0.10	0.15 × 0.08 × 0.07	0.50 × 0.10 × 0.05

Data collection
Diffractometer	Kappa-CCD diffractometer	Kappa-CCD diffractometer	Kappa-CCD diffractometer	Kappa-CCD diffractometer
Absorption correction	Multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	Multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	Multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	Multi-scan DENZO-SMN (Otwinowski & Minor, 1997)
T_min, T_max	0.929, 0.950	0.599, 0.774	0.641, 0.836	0.763, 0.876
No. of measured, independent and observed [I > 2σ(I)] reflections	7432, 2777, 1865	11972, 2685, 2327	7436, 2829, 1954	5744, 2731, 2033
R_int	0.057	0.079	0.077	0.039
(sin θ/λ)_max (Å⁻¹)	0.649	0.649	0.649	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.074, 0.98	0.039, 0.101, 1.07	0.042, 0.098, 1.01	0.032, 0.063, 0.95
No. of reflections	2777	2685	2829	2731
No. of parameters	163	163	163	163
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.07, −1.01	1.44, −1.25	0.97, −1.43	0.97, −0.97
Absolute structure	?	?	?	?
Absolute structure parameter	?	?	?	?

	(V)	(VI)	(VII)	(VIII)
Crystal data
Chemical formula	C₁₃H₉IN₂O₂	C₁₃H₉IN₂O₂	C₁₃H₉IN₂O₂	C₁₃H₉IN₂O₂
M_r	352.12	352.12	352.12	352.12
Crystal system, space group	Orthorhombic, P2₁2₁2₁	Orthorhombic, P2₁2₁2₁	Monoclinic, C2/c	Triclinic, P1
Temperature (K)	120	120	120	120
a, b, c (Å)	7.4741 (3), 11.3487 (4), 14.2039 (6)	7.1179 (2), 12.3905 (3), 13.6983 (5)	52.458 (2), 4.3786 (2), 23.5973 (13)	7.2646 (1), 11.8251 (2), 15.0057 (3)
α, β, γ (°)	90, 90, 90	90, 90, 90	90, 114.185 (2), 90	103.2458 (6), 98.3999 (7), 91.6291 (10)
V (Å³)	1204.79 (8)	1208.11 (6)	4944.4 (4)	1238.74 (4)
Z	4	4	16	4
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	2.65	2.65	2.59	2.58
Crystal size (mm)	0.20 × 0.06 × 0.06	0.20 × 0.10 × 0.10	0.15 × 0.04 × 0.03	0.28 × 0.10 × 0.08

Data collection
Diffractometer	Kappa-CCD diffractometer	Kappa-CCD diffractometer	Kappa-CCD diffractometer	Kappa-CCD diffractometer
Absorption correction	Multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	Multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	Multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	Multi-scan DENZO-SMN (Otwinowski & Minor, 1997)
T_min, T_max	0.665, 0.853	0.607, 0.768	0.893, 0.928	0.587, 0.814
No. of measured, independent and observed [I > 2σ(I)] reflections	8100, 2752, 2275	6019, 2627, 2453	13621, 5417, 2368	18561, 5602, 4991
R_int	0.117	0.033	0.128	0.076
(sin θ/λ)_max (Å⁻¹)	0.649	0.649	0.649	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.100, 1.00	0.029, 0.078, 1.11	0.059, 0.099, 0.84	0.030, 0.077, 1.03
No. of reflections	2752	2627	5417	5602
No. of parameters	163	163	325	325
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.03, −1.52	0.69, −1.08	1.23, −0.95	0.66, −1.18
Absolute structure	Flack (1983), 1141 Friedel pairs	Flack (1983), 1023 Friedel pairs	?	?
Absolute structure parameter	−0.03 (4)	−0.07 (3)	?	?

Computer programs: Kappa-CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997b), PLATON (Spek, 2002), SHELXL97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) for (I) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2	0.95	2.37	2.723 (5)	102

Hydrogen-bond geometry (Å, º) for (II) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱ	0.95	2.60	3.538 (6)	172
C26—H26···O2ⁱ	0.95	2.59	3.286 (6)	131

Symmetry code: (i) x+1, y, z+1.

Hydrogen-bond geometry (Å, º) for (III) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1ⁱ	0.95	2.44	3.331 (6)	156

Symmetry code: (i) x, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) for (IV) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O1ⁱ	0.95	2.45	3.397 (4)	174

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) for (V) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1ⁱ	0.95	2.58	3.437 (8)	151

Symmetry code: (i) −x+1/2, −y+1, z+1/2.

Hydrogen-bond geometry (Å, º) for (VI) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O2ⁱ	0.95	2.56	3.487 (6)	166

Symmetry code: (i) −x+1/2, −y+1, z+1/2.

Hydrogen-bond geometry (Å, º) for (VII) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O31	0.95	2.46	3.140 (11)	129
C17—H17···O12	0.95	2.34	2.742 (13)	105
C37—H37···O31	0.95	2.28	2.700 (11)	106
C33—H33···O32ⁱ	0.95	2.47	3.370 (12)	158
C34—H34···O11ⁱⁱ	0.95	2.57	3.327 (12)	137

Symmetry codes: (i) −x+1, −y−1, −z+1; (ii) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) for (VIII) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O31	0.95	2.43	3.303 (3)	153
C37—H37···O11ⁱ	0.95	2.53	3.406 (3)	154

Symmetry code: (i) −x+1, −y+1, −z+1.

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Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text