Isomeric N-(iodo­phenyl)nitrobenzamides form different three-dimensional framework structures

The isomeric N-(iodophenyl)nitrobenzamides, C₁₃H₉IN₂O₃, all form different three-dimensional framework structures. Molecules of N-(2-iodophenyl)-3-nitrobenzamide (II) are linked by a combination of N—H⋯O and C—H⋯O hydrogen bonds and a two-centre iodo⋯carbonyl interaction. The supramolecular structure of N-(2-iodophenyl)-4-nitrobenzamide (III) is built from one N—H⋯O and two C—H⋯O hydrogen bonds, but short I⋯O contacts are absent from the structure. In N-(3-iodophenyl)-2-nitrobenzamide (IV), which crystallizes with Z′ = 2 in space group P2₁, the structure contains two N—H⋯O hydrogen bonds, four C—H⋯O hydrogen bonds, two two-centre iodo⋯nitro interactions and an aromatic π⋯π stacking interaction. The structure of N-(3-iodophenyl)-3-nitrobenzamide (V) contains one N—H⋯O hydrogen bond and three C—H⋯O hydrogen bonds, together with a two-centre iodo⋯nitro interaction and an aromatic π⋯π stacking interaction, while in N-(3-iodophenyl)-4-nitrobenzamide (VI), the combination of one N—H⋯O hydrogen bond and two C—H⋯O hydrogen bonds is augmented not only by a two-centre iodo⋯nitro interaction and an aromatic π⋯π stacking interaction, but also by a dipolar carbonyl⋯carbonyl interaction. In the supramolecular structure of N-(4-iodophenyl)-4-nitrobenzamide (IX), which crystallizes with Z′ = 2 in space group , there are two N—H⋯O hydrogen bonds, four C—H⋯O hydrogen bonds and two three-centre iodo⋯nitro interactions.

1. Introduction

As part of a general study of the interplay of hydrogen bonds, iodo⋯nitro interactions and aromatic π⋯π stacking interactions in aromatic systems containing both iodo and nitro substituents, we have recently reported the molecular and supramolecular structures of a range of diaryl species (see Scheme 1) containing a variety of spacer units X, including the two isomeric series of arenesulfonamides (A) and (B) (Kelly et al., 2002), the two isomeric series of Schiff-base imines (C)

(Wardell et al., 2002) and (D) (Glidewell, Howie et al., 2002; Ferguson et al., 2005), benzylanilines (E) (Glidewell, Low et al., 2002, 2004), a single example of a benzamide (F) (Wardell et al., 2005), and 2,3-diazabutadienes (G) (Glidewell, Low, Skakle & Wardell, 2005; Low et al., 2006).

In the case of the Schiff-base imines of type (D), we were able to study the supramolecular aggregation modes in eight of the possible nine isomers (Glidewell, Howie et al., 2002); in the benzylaniline series (E) we were able to study the structures of six of the possible nine isomers (Glidewell, Low et al., 2002, 2004); and in the diazabutadiene series (G), we have been able to study four of the six possible isomers (Glidewell, Low, Skakle & Wardell, 2005<; Low et al., 2006). In each of these series, the interplay of the various weak intermolecular interactions is such that neither the supramolecular structure nor even the range of interactions involved can readily be predicted for any single example from a detailed knowledge of all the rest of the series. With this in mind, we have now expanded our preliminary study (Wardell et al., 2005) of the benzamide series (F) to incorporate a total of seven isomers of this series, compounds (I)–(VI) and (IX).

This series of isomers offers, within a fairly compact mol­ecular constitution, a wide variety of potential intermolecular interactions; these include N—H⋯O and C—H⋯O hydrogen bonds, in each of which the acceptor could be either a carbonyl O or a nitro O atom; N—H⋯π(arene) and C—H⋯π(arene) hydrogen bonds; iodo⋯carbonyl and iodo⋯nitro interactions, of which the latter could be of either two-centre or three-centre type; aromatic π⋯π stacking interactions; and dipolar carbonyl⋯carbonyl and nitro⋯nitro interactions.

2. Experimental

2.1. Synthesis

For the preparation of compounds (II)–(IX), equimolar quantities of the appropriate nitrobenzoyl chloride and the appropriate iodoaniline (2 mmol of each component) were dissolved in chloroform (50 cm³), and these mixtures were heated under reflux for 1 h. After cooling the mixtures, the solvent was removed under reduced pressure, and the resulting products were recrystallized from ethanol, yielding the pure compounds (II)–(IX): m.p. (II) 441–443 K, (III) 469–471 K (decomposes), (IV) 431–432 K, (V) 450–452 K, (VI) 471–472 K, (VII) 426–427 K, (VIII) 464–466 K, (IX) > 510 K. IR (KBr disk, cm⁻¹): (II) 3249, 1658, 1639, 1587, 1522, 1343; (III) 3278, 1654, 1586, 1522, 1353; (IV) 3378, 3321, 1680, 1648, 1582, 1524, 1347; (V) 3309, 1656, 1589, 1521, 1346; (VI) 3298, 1645, 1587, 1525, 1346; (VII) 3281, 1655, 1574, 1525, 1347; (VIII) 3409, 1677, 1587, 1516, 1344; (IX) 3290, 1652, 1585, 1510, 1349. Crystals of isomers (II)–(VI) suitable for single-crystal X-ray diffraction were grown from solutions in ethanol; suitable crystals of isomer (IX) could not be obtained in this way, but were grown from a solution in acetone. Repeated attempts were made to obtain adequate crystals of isomers (VII) and (VIII), and for both isomers crystallization was attempted from each of acetone, acetonitrile, chloroform, ethanol, methanol and various ethanol–water mixtures, all without success.

2.2. Data collection, structure solution and refinement

Diffraction data for isomers (II)–(VI) were collected at 120 (2) K using a Nonius KappaCCD diffractometer; in all these cases graphite-monochromated Mo K_α radiation (λ = 0.71073 Å) was employed. Data for isomer (IX) were collected at 120 (2) K on Daresbury SRS Station 9.8 (Cernik et al., 1997; Clegg, 2000) using a Bruker SMART APEXII diffractometer and synchrotron radiation (λ = 0.6712 Å) Other details of cell data, data collection and refinement are summarized in Table 1, together with details of the software employed (Bruker, 2001, 2003; Ferguson, 1999; Hooft, 1999; McArdle, 2003; Otwinowski & Minor, 1997; Sheldrick, 1997; Sheldrick, 2003). For isomer (VIII) no usable diffraction data could be obtained even using synchrotron radiation.

Table 1
Experimental details

	(II)	(III)	(IV)	(V)	(VI)	(IX)
Crystal data
Chemical formula	C13H9IN2O3	C13H9IN2O3	C13H9IN2O3	C13H9IN2O3	C13H9IN2O3	C13H9IN2O3
Mr	368.12	368.12	368.12	368.12	368.12	368.12
Cell setting, space group	Monoclinic, P21/c	Monoclinic, Pc	Monoclinic, P21	Monoclinic, Cc	Monoclinic, P21/n	Triclinic,
Temperature (K)	120 (2)	120 (2)	120 (2)	120 (2)	120 (2)	120 (2)
a, b, c (Å)	13.1804 (3), 7.5099 (2), 13.8849 (3)	10.0528 (3), 4.8703 (10), 13.5719 (3)	11.0552 (3), 8.9521 (2), 12.8921 (3)	13.8494 (4), 10.0495 (3), 9.4203 (3)	7.4798 (2), 14.0889 (7), 11.8138 (6)	5.1047 (3), 15.3015 (9), 16.4806 (9)
α, β, γ (°)	90.00, 111.1634 (12), 90.00	90.00, 109.9452 (17), 90.00	90.00, 96.3899 (10), 90.00	90.00, 105.2353 (16), 90.00	90.00, 93.259 (3), 90.00	95.356 (2), 95.498 (2), 91.150 (2)
V (Å^3)	1281.68 (5)	624.63 (13)	1267.97 (5)	1265.03 (7)	1242.95 (9)	1275.23 (13)
Z	4	2	4	4	4	4
Dx (Mg m^−3)	1.908	1.957	1.928	1.933	1.967	1.917
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα	Mo Kα	Synchrotron
μ (mm^–1)	2.50	2.57	2.53	2.54	2.58	2.52
Crystal form, colour	Plate, colourless	Plate, brown	Plate, colourless	Block, brown	Needle, brown	Needle, colourless
Crystal size (mm)	0.50 × 0.10 × 0.02	0.42 × 0.30 × 0.08	0.40 × 0.20 × 0.08	0.46 × 0.34 × 0.16	0.48 × 0.09 × 0.07	0.09 × 0.04 × 0.02
Data collection
Diffractometer	Bruker–Nonius KappaCCD	Bruker–Nonius KappaCCD	Bruker–Nonius KappaCCD	Bruker–Nonius KappaCCD	Bruker–Nonius KappaCCD	Bruker SMART APEXII CCD
Data collection method	φ and ω scans	φ and ω scans	φ and ω scans	φ and ω scans	φ and ω scans	Fine–slice ω scans
Absorption correction	Multi-scan	Multi-scan	Multi-scan	Multi-scan	Multi-scan	Multi-scan
Tmin	0.368	0.412	0.431	0.376	0.370	0.805
Tmax	0.952	0.821	0.823	0.666	0.840	0.951
No. of measured, independent and observed reflections	15 482, 2942, 2549	10 157, 2767, 2624	16 241, 5672, 5506	7022, 2797, 2752	13 030, 2843, 2529	13 690, 7348, 6485
Criterion for observed reflections	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)
Rint	0.038	0.026	0.024	0.023	0.060	0.020
θmax (°)	27.6	27.5	27.5	27.5	27.6	28.7
Refinement
Refinement on	F^2	F^2	F^2	F^2	F^2	F^2
R[F^2 > 2σ(F^2)], wR(F^2), S	0.025, 0.062, 1.07	0.019, 0.048, 1.21	0.020, 0.046, 1.11	0.018, 0.053, 1.24	0.084, 0.286, 1.17	0.029, 0.074, 1.04
No. of reflections	2942	2767	5672	2797	2843	7348
No. of parameters	172	173	344	172	161	337
H-atom treatment	Constrained to parent site	Constrained to parent site	Constrained to parent site	Constrained to parent site	Constrained to parent site	Constrained to parent site
Weighting scheme	w = 1/[σ^2(Fo^2) + (0.0327P)^2 + 0.5883P], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.022P)^2], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.0177P)^2 + 0.1391P], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.0227P)^2], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.1676P)^2 + 25.4085P], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.0386P)^2 + 0.6363P], where P = (Fo^2 + 2Fc^2)/3
(Δ/σ)max	0.001	<0.0001	0.001	<0.0001	<0.0001	0.002
Δρmax, Δρmin (e Å^−3)	0.58, −0.98	0.67, −0.62	0.66, −0.80	0.56, −1.09	3.92, −2.57	0.91, −1.02
Extinction method	None	SHELXL97	SHELXL97	None	None	None
Extinction coefficient	–	0.0225 (11)	0.0075 (3)	–	–	–
Absolute structure	–	Flack (1983), 1328 Friedel pairs	Flack (1983), 2565 Friedel pairs	Flack (1983), 1349 Friedel pairs	–	–
Flack parameter	–	−0.006 (17)	−0.008 (11)	0.013 (17)	–	–
Computer programs used: COLLECT (Hooft, 1999), APEX2 (Bruker, 2003), DENZO (Otwinowski & Minor, 1997), SAINT (Bruker, 2001), OSCAIL (McArdle, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PRPKAPPA (Ferguson, 1999), SADABS (Sheldrick, 2003).

For isomers (II) and (VI) the space groups P2₁/c and P2₁/n, respectively, were uniquely assigned from the systematic absences; crystals of isomer (IX) are triclinic and the space group was selected, and subsequently confirmed by the successful structure analysis. For each of (III)–(V) the systematic absences provided a choice of space groups: Pc or P2/c for isomer (III), P2₁ or P2₁/m for isomer (IV), and Cc or C2/c for isomer (V). The space groups Pc, P2₁ and Cc, respectively, were selected, and confirmed by the subsequent structure analyses.

The structures were solved by direct methods and refined with all data on F². A weighting scheme based on P = (F_o² + 2F_c²)/3 was employed in order to reduce statistical bias (Wilson, 1976). All H atoms were located from difference maps and then treated as riding atoms with C—H distances of 0.95 Å and N—H distances of 0.88–0.90 Å, and with U_iso(H) = 1.2U_eq(C,N). The correct absolute configuration for the molecules in the crystal of isomer (IV) selected for data collection was determined by means of the Flack (1983) parameter; for isomers (III) and (V) the correct orientations of the structures with respect to the polar axis directions were established by means of their Flack parameters. For compound (VI), PLATON (Spek, 2003) indicated the presence of non-merohedral twinning, and the refined twin fractions were 0.323 (4) and 0.677 (4).

Supramolecular analyses were made and the diagrams were prepared with the aid of PLATON (Spek, 2003). Details of molecular conformations are given in Table 2, details of hydrogen-bond dimensions are given in Table 3, and details of short I⋯O interactions are given in Table 4.¹ Figs. 1–6 show the molecular components, with the atom-labelling schemes, and Figs. 7–12 show aspects of the supramolecular structures.

Table 2
Selected torsion angles (°)

(a) Isomers with Z′ = 1.

Parameter	(I)†	(II)	(III)	(V)	(VI)
C11—C17—N1—C21	−173.38 (16)	−169.3 (2)	−165.0 (3)	175.5 (2)	177.2 (10)
C12—C11—C17—N1	76.1 (2)	−169.8 (2)	26.8 (4)	−25.2 (4)	167.6 (10)
C22—C21—N1—C17	−143.98 (19)	116.5 (3)	138.7 (3)	25.7 (4)	18.3 (18)

(b) Isomers with Z′ = 2.

Parameter	(IV)	(IX)
C11—C17—N11—C21	−177.8 (3)	177.53 (18)
C31—C37—N31—C41	−170.2 (2)	−179.62 (18)
C12—C11—C17—N11	96.5 (3)	−144.7 (2)
C32—C31—C37—N31	71.4 (4)	146.52 (19)
C22—C21—N11—C17	−13.2 (4)	−27.9 (3)
C42—C41—N31—C37	31.1 (4)	−38.8 (3)

†Data for compound (I) are taken from Wardell et al. (2005).

Table 3
Hydrogen-bond parameters (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A	Motif	Direction
(II)
N1—H1⋯O17^i	0.88	2.16	2.950 (3)	149	C(4)	[010]
C23—H23⋯O31^ii	0.95	2.45	3.385 (4)	169	C(11)	[100]
(III)
N1—H1⋯O17^iii	0.88	2.07	2.920 (3)	164	C(4)	[010]
C24—H24⋯O42^iv	0.95	2.34	3.175 (5)	147	C(13)	[20]
C26—H26⋯Cg1^v†	0.95	2.95	3.800 (3)	149	–	[001]
(IV)
N11—H11⋯O17^vi	0.88	2.28	2.977 (3)	137	C(4)	[010]
N31—H31⋯O37^vii	0.88	2.01	2.863 (3)	162	C(4)	[010]
C14—H14⋯O321^viii	0.95	2.48	3.244 (4)	137	C2^2(7)	[010]
C15—H15⋯O322	0.95	2.41	3.245 (4)	147	D	–
C16—H16⋯O121^vi	0.95	2.55	3.416 (4)	151	C(6)	[010]
C35—H35⋯O122^ix	0.95	2.44	3.251 (5)	143	C2^2(14)	[10]
(V)
N1—H1⋯O17^v	0.88	2.08	2.937 (3)	165	C(4)	[001]
C12—H12⋯.O17^v	0.95	2.48	3.266 (4)	140	C(5)	[001]
C24—H24⋯O31^x	0.95	2.48	3.371 (4)	157	C(12)	[10]
C26—H26⋯O17^v	0.95	2.51	3.256 (5)	136	C(6)	[001]
(VI)
N1—H1⋯O41^xi	0.88	2.33	3.191 (13)	167	C(9)	[101]
C16—H16⋯O41^xi	0.95	2.40	3.291 (14)	155	C(6)	[101]
C24—H24⋯O17^xii	0.95	2.36	3.192 (15)	147	C(8)	[101]
(IX)
N11—H11⋯O17^ii	0.90	2.06	2.936 (2)	163	C(4)	[100]
N31—H31⋯O37^xiii	0.90	2.04	2.915 (2)	164	C(4)	[100]
C13—H13⋯O141^xiv	0.95	2.41	3.233 (4)	145	R2^2(10)	–
C15—H15⋯O342	0.95	2.40	3.305 (4)	159	D	–
C33—H33⋯O341^xv	0.95	2.50	3.231 (3)	134	R2^2(10)	–
C35—H35⋯O142	0.95	2.36	3.254 (3)	157	D	–
Symmetry codes: (i) ; (ii) 1 + x, y, z; (iii) x, -1 + y, z; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) -1 + x, 1 + y, z; (x) ; (xi) ; (xii) ; (xiii) -1 + x, y, z; (xiv) -x, 1 - y, 1 - z; (xv) 3 - x, -y, 1 - z.

†Cg1 is the centroid of ring C11–C16.

Table 4
Geometric parameters (Å, ^o) for I⋯O contacts

C—I⋯O	C—I	I⋯O	C—I⋯O	Motif	Direction
(II)
C22—I22⋯.O17^i	2.101 (2)	3.069 (2)	175.6  (2)	C(6)	[001]
(IV)
C23—I23⋯O37^ii	2.103 (3)	3.164 (2)	173.7 (2)	C2^2(16)	[01]
C43—I43⋯O17^iii	2.108 (3)	3.233 (2)	166.6 (2)	C2^2(16)	[01]
(V)
C23—I23⋯O32^iv	2.103 (4)	3.190 (3)	160.5 (2)	C(11)	[11]
(VI)
C23—I23⋯O42^v	2.106 (11)	3.243 (8)	157.7 (3)	C(12)	[010]
(IX)
C24—I24⋯O141^vi	2.095 (2)	3.438 (2)	155.4 (2)	C(13)	[001]
C24—I24⋯O142^vi	2.095 (2)	3.394 (2)	167.5 (2)	C(13)	[001]
C44—I44⋯O341^vii	2.096 (2)	3.512 (2)	154.6 (2)	C(13)	[001]
C44—I44⋯O342^vii	2.096 (2)	3.368 (2)	166.1 (2)	C(13)	[001]
Symmetry codes: (i) ; (ii) x, -1 + y, 1 + z; (iii) x, 1 + y, -1 + z; (iv) ; (v) x, -1 + y, z; (vi) x, y, 1 + z; (vii) x, y, -1 + z.

Figure 1 A molecule of isomer (II) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2 A molecule of isomer (III) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 3 The two independent molecules in isomer (IV) showing the atom-labelling scheme and the C—H⋯O hydrogen bond within the selected asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.

Figure 4 A molecule of isomer (V) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 5 A molecule of isomer (VI) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 6 The two independent molecules of isomer (IX) showing the atom-labelling scheme and the hydrogen bonds within the selected asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.

Figure 7 (a) Part of the crystal structure of isomer (II) showing the formation of a sheet of R4^4(28) rings parallel to (001) generated by the N—H⋯O and C—H⋯O hydrogen bonds. For the sake of clarity, the H atoms not involved in the motifs shown have been omitted. The atoms marked with an asterisk (*), a hash (#), a dollar sign ($), an ampersand (&) or an `at' sign (@) are at the symmetry positions (1 − x, + y, − z), (1 + x, y, z), (2 − x, − + y, − z), (1 − x, − + y, − z) and (2 − x, + y, − z), respectively. (b) Part of the crystal structure of isomer (II) showing the formation of the C(6) iodo⋯carbonyl chain along [001]. For the sake of clarity, all of the H atoms have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, − y, − + z) and (x, − y, + z), respectively.

Figure 8 (a) Part of the crystal structure of isomer (III) showing the formation of a sheet of R4^4(32) rings parallel to (102) generated by the N—H⋯O and C—H⋯O hydrogen bonds. For the sake of clarity, the H atoms not involved in the motifs shown have been omitted. The atoms marked with an asterisk (*), a hash (#), a dollar sign ($), an ampersand (&) or an `at' sign (@) are at the symmetry positions (x, −1 + y, z), (1 + x, 1 − y, − + z), (1 + x, −y, − + z), (x, 1 + y, z) and (1 + x, 2 − y, − + z), respectively. (b) Part of the crystal structure of isomer (III) showing the formation of a chain along [001] generated by the C—H⋯π(arene) hydrogen bond. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, 1 − y, − + z) and (x, 1 − y, + z), respectively.

Figure 9 (a) A stereoview of part of the crystal structure of isomer (IV) showing the formation of a sheet of R6^6(34) rings parallel to (10) generated by the two N—H⋯O hydrogen bonds and the C—H⋯O hydrogen bond within the asymmetric unit. For the sake of clarity, the H atoms not involved in the motifs shown have been omitted. (b) Part of the crystal structure of isomer (IV) showing the formation of a C2^2(14) chain along [10] generated by two C—H⋯O hydrogen bonds. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (−1 + x, 1 + y, z) and (1 + x, −1 + y, z), respectively. (c) A stereoview of part of the crystal structure of isomer (IV) showing the formation of a C2^2(16)C2^2(16)[R2^2(14)] chain of rings along [01] generated by one C—H⋯O hydrogen bond and two iodo⋯carbonyl interactions. For the sake of clarity, the H atoms other than H15 have been omitted.

Figure 10 (a) Part of the crystal structure of isomer (V) showing the formation of a chain of rings along [001] generated by one N—H⋯O hydrogen bond and two C—H⋯O hydrogen bonds. For the sake of clarity, the H atoms not involved in the motifs shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, 1 − y, − + z) and (x, 1 − y, + z), respectively. (b). Part of the crystal structure of isomer (V) showing the formation of a C(12) chain along [10] generated by a single C—H⋯O hydrogen bond. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (− + x, − y, + z) and ( + x, − y, − + z), respectively. (c) Part of the crystal structure of isomer (V) showing the formation of a C(11) chain along [11] generated by a two-centre iodo⋯nitro interaction. For the sake of clarity, all of the H atoms have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (− + x, − + y, 1 + z) and ( + x, + y, −1 + z), respectively. (d) A stereoview of part of the crystal structure of isomer (V) showing the formation of a π-stacked chain along [110]. For the sake of clarity, all of the H atoms have been omitted.

Figure 11 A stereoview of part of the crystal structure of isomer (VI) showing the formation of a hydrogen-bonded sheet parallel to (10), which is reinforced by a two-centre iodo⋯nitro interaction. For the sake of clarity, the H atoms not involved in the motifs shown have been omitted

Figure 12 (a) A stereoview of part of the crystal structure of isomer (IX) showing the formation of a chain along [100] comprising edge-fused R2^2(10) and R4^4(30) rings. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. (b) A stereoview of part of the crystal structure of isomer (IX) showing the formation of a chain along [30] containing three types of R2^2(10) ring. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. (c) A stereoview of part of the crystal structure of isomer (IX) showing the formation of a chain along [001] comprising edge-fused R2^2(10) and R4^2(24) rings. For the sake of clarity, the H atoms not involved in the motif shown have been omitted.

3. Results and discussion

3.1. Molecular conformations

In each isomer (Figs. 1–6) the central amidic portion adopts a nearly planar trans conformation, as shown by the C11—C17—N1—C21 torsion angles in the isomers (I)–(III), (V) and (VI) having Z′ = 1, and the corresponding angles C11—C17—N11—C21 and C31—C37—N31—C41 for the isomers (IV) and (IX) having Z′ = 2 (Table 2). However, the two independent torsion angles defining the orientation of the two aryl rings relative to the central amide group show a very wide range of values, such that none of the molecular skeletons even approaches planarity. In addition, the nitro groups make modest non-zero dihedral angles with the adjacent aryl rings, ranging from 1.4 (2)° in isomer (IV) to 16.1 (2)° in isomer (III).

The range of molecular conformations in the crystalline state indicates that the direction-specific intermolecular forces, in particular the hydrogen bonds and the iodo⋯oxygen interactions, are capable of overcoming the rotational barriers associated with the bonds linking the rings to the central spacer unit. Despite the marked non-planarity, it is still possible to identify in each isomer two distinct edges of the elongated molecules, while the 4- and 4′-positions can be regarded as forming the ends of the molecules. Where neither the iodo nor the nitro substituent occupies a 4- or 4′-site, the ring orientations are such that in isomers (I), (II) and (V) these substituents are on opposite edges of the molecule, while in isomer (IV) they are on the same edge. Since in each of these isomers the rings are involved in direction-specific intermolecular interactions, it may be concluded that the sum of the resultant forces in any isomer can overcome the two independent intramolecular rotational barriers constraining the orientations of the aryl rings relative to the central amide spacer unit.

3.2. Supramolecular structures

3.2.1. Isomer (I), N-(2-iodophenyl)-2-nitrobenzamide

The molecules of (I) are linked into a three-dimensional structure, which was described (Wardell et al., 2005) in terms of three simple one-dimensional sub-structures built, respectively, from an N—H⋯O hydrogen bond, a combination of a C—H⋯O hydrogen bond and a two-centre iodo⋯nitro interaction, and a C—H⋯π(arene) hydrogen bond, and running, respectively, along the [100], [010] and [001] directions.

3.2.2. Isomer (II), N-(2-iodophenyl)-3-nitrobenzamide

The molecules of isomer (II) (Fig. 1) are linked into sheets by a combination of two hydrogen bonds, one each of N—H⋯O and C—H⋯O types (Table 3), and the hydrogen-bonded sheets are linked into a three-dimensional framework structure by a single two-centre iodo⋯carbonyl interaction (Table 4).

Atom N1 in the molecule at (x, y, z) acts as a hydrogen-bond donor to the amidic atom O17 in the molecule at (1 − x,  + y, − z), so forming a C(4) (Bernstein et al., 1995) chain typical of carboxamides, running parallel to the [010] direction and generated by the 2₁ screw axis along (, y, ). In addition, atom C23 in the molecule at (x, y, z) acts as a hydrogen-bond donor to the nitro atom O31 in the molecule at (1 + x, y, z), so generating by translation a C(11) chain running parallel to the [100] direction. The combination of the C(4) and C(11) chains along [010] and [100], respectively, then generates a (001) sheet in the form of a (4,4)-net built from a single type of R₄⁴(28) ring (Fig. 7a).

Adjacent sheets are linked by the iodo⋯carbonyl interaction (Table 3). Atom I22 in the molecule at (x, y, z), which lies in the (001) sheet generated by the screw axes at z = , makes a short two-centre contact with the amidic atom O17 in the molecule at (x, − y, − + z), which forms part of the (001) sheet generated by the screw axes at z = −. Propagation of this interaction forms a C(6) (Starbuck et al., 1999) chain running parallel to the [001] direction and generated by the c-glide plane at y = (Fig. 7b). The combination of the (001) hydrogen-bonded sheets and the [001] iodo⋯carbonyl chain is sufficient to generate a continuous framework structure.

3.2.3. Isomer (III), N-(2-iodophenyl)-4-nitrobenzamide

The molecules of isomer (III) (Fig. 2) are linked into a three-dimensional framework by three hydrogen bonds, one each of N—H⋯O, C—H⋯O and C—H⋯π(arene) types (Table 3), and the formation of the framework can readily be analysed in terms of three one-dimensional sub-structures, each containing just a single type of hydrogen bond.

In the simplest of the three sub-structures, atom N1 in the molecule at (x, y, z) acts as a hydrogen-bond donor to amidic atom O17 in the molecule at (x, −1 + y, z), so generating by translation the C(4) chain motif characteristic of carboxamides, here running parallel to the [010] direction. The second sub-structure is generated by the C—H⋯O hydrogen bond; atom C24 in the molecule at (x, y, z) acts as a donor to the nitro atom O42 in the molecule at (1 − x, 1 − y, − + z), so forming a C(13) chain running parallel to the [20] direction and generated by the c-glide plane at y = . The combination of the C(4) and C(13) chains generates a (102) sheet in the form of a (4,4)-net built from a single type of R₄⁴(32) ring (Fig. 8a). In the final sub-structure, atom C26 in the molecule at (x, y, z) acts as a hydrogen-bond donor to the aryl ring C11–C16 of the molecule at (x, 1 − y, − + z), so producing a chain running parallel to the [001] direction, again generated by the c-glide plane at y = (Fig. 8b). The combination of all three of the one-dimensional sub-structures then generates a three-dimensional framework structure.

3.2.4. Isomer (IV), N-(3-iodophenyl)-2-nitrobenzamide

Isomer (IV) crystallizes with Z′ = 2 in space group P2₁, and the molecules are linked into a three-dimensional framework of considerable complexity by means of two N—H⋯O hydrogen bonds, four C—H⋯O hydrogen bonds (Table 3), two iodo⋯nitro interactions, both of two-centre type (Table 4), and a single aromatic π⋯π stacking interaction; C—H⋯π(arene) hydrogen bonds are, however, absent.

The asymmetric unit (Fig. 3) was selected to contain the C—H⋯O hydrogen bond with the shortest H⋯O distance, and there are thus seven independent interactions linking these two-molecule aggregates. Each of the independent molecules, type 1 containing N11 and type 2 containing N31, forms a C(4) chain running parallel to the [010] direction and containing a single type of N—H⋯O hydrogen bond (Table 3). The chain of type 1 molecules is generated by the 2₁ screw axis along (, y, ), while the chain of type 2 molecules is generated by the 2₁ screw axis along (0, y, 0). The formation of the type 1 chain is weakly augmented by an aromatic π⋯π stacking interaction. The nitrated ring C11–C16 of the type 1 molecule at (x, y, z) and the iodinated ring C21–C26 of the type 1 molecule at (1 − x, − + y, 1 − z) are inclined to one another at only 5.1 (2)°: the corresponding ring-centroid separation is 3.735 (2) Å with an interplanar spacing of ca 3.40 Å and a ring offset of ca 1.55 Å.

In combination with the C—H⋯O hydrogen bond within the asymmetric unit, the two C(4) chains generate a (10) sheet containing a single type of R₆⁶(34) ring (Fig. 9a). The (10) sheets are linked to form the overall three-dimensional framework by two readily identifiable and rather simple one-dimensional sub-structures, one built from two C—H⋯O hydrogen bonds, and the other built from two iodo⋯carbonyl interactions.

Atom C35 in the type 2 molecule at (x, y, z) acts as a hydrogen-bond donor to the nitro atom O122 in the type 1 molecule at (−1 + x, 1 + y, z): in combination with the C—H⋯O hydrogen bond within the asymmetric unit, this interaction then generates by translation a C₂²(14) chain running parallel to the [10] direction (Fig. 9b). Finally, atoms I23 and I43 in the aggregate at (x, y, z) form nearly linear two-centre contacts with, respectively, the carbonyl atoms O37 at (x, −1 + y, 1 + z) and O17 at (x, 1 + y, −1 + z) which, in combination with the C—H⋯O hydrogen bond within the asymmetric unit, generates by translation a C₂²(16)C₂²(16)[R₂²(14)] chain of rings running parallel to the [01] direction (Fig. 9c). Either of these chain motifs is sufficient to link adjacent (10) sheets into a single three-dimensional framework.

3.2.5. Isomer (V), N-(3-iodophenyl)-3-nitrobenzamide

In the supramol­ecular structure of isomer (V) (Fig. 4), which is three-dimensional, it is possible to identify four independent one-dimensional sub-structures: one is built from an N—H⋯O hydrogen bond, augmented by two C—H⋯O hydrogen bonds, where all three interactions utilize a single acceptor (Table 3); another is built from just a single C—H⋯O hydrogen bond (Table 3); a third sub-structure is built from a two-centre iodo⋯nitro interaction (Table 4); finally, there is a one-dimensional sub-structure built from an aromatic π⋯π stacking interaction.

Atoms N1, C12 and C26 in the molecule at (x, y, z) all act as hydrogen-bond donors to the amidic atom O17 in the mol­ecule at (x, 1 − y, − + z). These hydrogen bonds individually give rise to chains of C(4), C(5) and C(6) types, respectively, all running parallel to the [001] direction and generated by the c-glide plane at y = ; together they generate a C(4)C(5)C(6)[R₂¹(6)][R₂¹(7)] chain of rings (Fig. 10a). The remaining C—H⋯O hydrogen bond (Table 2) generates a simple chain motif; atom C24 in the molecule at (x, y, z) acts as a donor to the nitro atom O31 in the molecule at (− + x, − y,  + z), so forming a C(12) chain running parallel to the [10] direction and generated by the n-glide plane at y = (Fig. 10b).

The iodo⋯nitro interaction (Table 4) likewise generates a simple chain. Atom I23 in the molecule at (x, y, z) forms a two-centre contact with the nitro atom O32 in the molecule at (− + x, − + y, 1 + z), so generating by translation a C(11) chain running parallel to the [11] direction (Fig. 10c). Finally, the nitrated ring C11–C16 in the molecule at (x, y, z) and the iodinated ring C21–C26 in the molecule at ( + x, + y, z) are almost parallel, with a dihedral angle between them of only 2.5 (2)°. The corresponding ring-centroid separation is 3.858(2) Å and the interplanar spacing is ca 3.48 Å, corresponding to a ring offset of ca 1.66 Å. Propagation by translation of this stacking interaction then generates a π-stacked chain running parallel to the [110] direction (Fig. 10d). The combination of [001], [10], [11] and [110] chains suffices to generate a complex three-dimensional framework.

3.2.6. Isomer (VI), N-(3-iodophenyl)-4-nitrobenzamide

The molecules of isomer (VI) (Fig. 5) are linked into sheets by a combination of one N—H⋯O hydrogen bond and two C—H⋯O hydrogen bonds (Table 3), reinforced by a two-centre iodo⋯nitro interaction (Table 4), and these sheets are linked into a three-dimensional framework structure by a combination of an aromatic π⋯π stacking interaction and a dipolar carbonyl⋯carbonyl interaction.

Atoms N1 and C126 in the molecule at (x, y, z) both act as hydrogen-bond donors to the atom O41 in the molecule at (− + x, − y, − + z), so forming a C(6)C(9)[R₂¹(7)] chain of rings running parallel to the [101] direction and generated by the n-glide plane at y = (Fig. 11). At the same time, atom C24 at (x, y, z) acts as a hydrogen-bond donor to atom O17 in the molecule at − + x, − y, − + z), thus forming a simple C(8) chain, also parallel to [101] but this time generated by the n-glide plane at y = . The combination of these two [101] chains generates a (10) sheet (Fig. 11) which also includes a nearly linear two-centre iodo⋯nitro interaction between atom I23 in the molecule at (x, y, z) and atom O42 in the molecule at (x, −1 + y, z) (Table 4), so forming a sheet containing three distinct types of ring, R₂¹(7), R₃³(17) and R₂³(18) (Bernstein et al., 1995; Starbuck et al., 1999).

The nitrated ring C11–C16 in the molecule at (x, y, z) makes dihedral angles of only 2.8 (2)° with the iodinated ring C21–C26 in each of the two molecules at (−x, 1 − y, 1 − z) and (1 − x, 1 − y, 1 − z). The ring-centroid separations are 3.714 (7) and 3.808 (7) Å, respectively, and the interplanar spacings are ca 3.49 and 3.44 Å, corresponding to ring offsets of ca 1.27 and 1.63 Å. The action of the weaker of the two π stacking interactions is reinforced by an antiparallel type (II) (Allen et al., 1998) dipolar interaction between the carbonyl groups in the molecules at (x, y, z) and (1 − x, 1 − y, 1 − z), with O⋯C(1 − x, 1 − y, 1 − z) = 3.195 (14) Å and C—O⋯C(1 − x, 1 − y, 1 − z) = 76.6 (7)°. The effect of these two types of interaction is the linking of each (10) sheet to its two immediate neighbours, so forming a continuous three-dimensional structure.

3.2.7. Isomer (IX), N-(4-iodophenyl)-4-nitrobenzamide

Isomer (IX) crystallizes with Z′ = 2 in space group ; the molecules containing atoms N11 and N31 (Fig. 6) are denoted as types 1 and 2, respectively. The molecules are linked into a complex three-dimensional framework by a combination of two N—H⋯O and four C—H⋯O hydrogen bonds (Table 3) and two independent three-centre iodo⋯nitro interactions (Table 4).

Within the selected asymmetric unit the molecules are linked by C—H⋯O hydrogen bonds defining an R₂²(10) motif, and it is convenient to regard this compact bimolecular aggregate as the basic building block in the overall structure. The first of the one-dimensional sub-structures is built from two independent N—H⋯O hydrogen bonds. Atoms N11 and N31 at (x, y, z) acts as hydrogen-bond donors, respectively, to atoms O17 at (1 + x, y, z) and O37 at (−1 + x, y, z). These two hydrogen bonds individually generate by translation two independent antiparallel C(4) chains running parallel to the [100] direction, one built exclusively of type 1 molecules and the other containing only type 2 molecules. In combination with the two C—H⋯O hydrogen bonds within the asymmetric unit, the N—H⋯O hydrogen bonds generate a [100] chain of edge-fused R₂²(10) and R₄⁴(30) rings (Fig. 12a).

The second one-dimensional motif is built solely from C—H⋯O hydrogen bonds. Atom C13 at (x, y, z) acts as a hydrogen-bond donor to atom O141 at (−x, 1 − y, 1 − z), so generating by inversion an R₂²(10) dimer of type 1 molecules centred at (0, , ); similarly, atom C33 at (x, y, z) acts as a donor to atom O341 at (3 − x, −y, 1 − z), generating a second centrosymmetric R₂²(10) dimer, this time containing type 2 molecules and centred at (, 0, ). These motifs combine with the hydrogen bonds within the asymmetric unit to generate a chain of edge-fused rings running parallel to the [30] direction, and containing three distinct types of R₂²(10) ring (Fig. 12b).

The final one-dimensional sub-structure is built from two independent three-centre iodo⋯nitro interactions, each involving just one type of molecule (Table 3). Atom I24 at (x, y, z) forms a nearly symmetrical I⋯(O)₂ contact with atoms O141 and O142 at (x, y, 1 + z), while atom I44 at (x, y, z) forms a similar, although less symmetrical, contact with atoms O341 and O342 at (x, y, −1 + z). The individual interactions generate by translation two independent antiparallel C(13)C(13)[R₂¹(4)] motifs (Starbuck et al., 1999), while the two together, in combination with the hydrogen bonds within the asymmetric unit, generate a chain of edge-fused R₂²(10) and R₄²(24) rings parallel to [001] (Fig. 12c).

The combination of the chains along [100], [001] and [30] suffices to generate a three-dimensional structure of considerable complexity.

3.3. General comparison of the structures

Although the isomers described here all adopt three-dimensional supramolecular structures, the range and identity of the direction-specific intermolecular forces is different in each isomer.

Taking firstly the isomers (I)–(III), (V) and (VI), which crystallize with Z′ = 1, these all contain a single N—H⋯O hydrogen bond but, as noted above (see §3.2), this involves a carbonyl O atom as the acceptor, except in isomer (VI), where a nitro O atom acts as the acceptor. The structures of all these isomers contain C—H⋯O hydrogen bonds, one in isomer (II), two in each of (I), (III) and (VI), and three in isomer (V); while these usually have nitro O atoms as the acceptor, carbonyl O atoms participate in isomers (V) and (VI). Iodo⋯carbonyl interactions are present only in isomer (II), while two-centre iodo⋯nitro interactions are present in each of (I), (V) and (VI); by contrast, there are no short I⋯O contacts of any sort in isomer (III). Isomer (II) does, however, present the sole example amongst all of these isomers of C—H⋯π(arene) hydrogen bonding. Aromatic π⋯π stacking interactions are present in each of the isomers (V) and (VI), but in none of the other Z′ = 1 isomers, while dipolar carbonyl⋯carbonyl interactions are observed only in the structure of isomer (VI).

Of the two isomers, (IV) and (IX), having Z′ = 2, both contain two independent N—H⋯O hydrogen bonds, all with carbonyl O acceptors, and both contain four independent C—H⋯O hydrogen bonds, all with nitro O acceptors. However, the iodo⋯nitro interactions are of two-centre type in isomer (IV), but of three-centre type in isomer (IX), while only the structure of isomer (IV) contains aromatic π⋯π stacking interactions.

Just as the range and number of distinct intermolecular interactions in any one of these isomers could not readily be predicted, even given a detailed knowledge of each of the other isomers, so too the detailed construction of the three-dimensional framework structure of any given isomer is not predictable from the structures of all of the others. Allied to this, even the crystallization characteristics show no discernible pattern; with the exception of isomers (II) and (VI), which have been analysed in two different settings of the same space group, no two of the isomers reported here adopt the same space group (Table 1), while isomer (I) crystallizes in P2₁2₁2₁ (Wardell et al., 2005); of the seven isomers whose structure are now known, no fewer than four crystallize in non-centrosymmetric space groups.

4. Concluding discussion

We have found in several earlier studies of closely related series of compounds, in particular in series of geometric isomers, that every member of a given series manifests in its crystal structure a different range of direction-specific intermolecular interactions, such that no individual structure could readily be predicted even with full a knowledge of the structures of every other member of the same series (Glidewell, Howie et al., 2002; Glidewell, Low et al., 2002, 2004). The same conclusion must be drawn from the structures described here: neither the molecular conformations nor the supramolecular aggregation patterns are readily predictable from one isomer to another. Equally, the variations in the space groups (Table 1) from one isomer to another are not readily explicable, nor whether the space group is centrosymmetric or non-centrosymmetric, nor whether the non-centrosymmetric structures are polar or non-polar. We have suggested above (§3.1) that in the present series the direction-specific intermolecular forces are well able to overcome the intramolecular rotational barriers defining the molecular conformations; consistent with this proposition is the observation of conformational polymorphism in the related series (D) (Ferguson et al., 2005), where the conformations are clearly determined by the intermolecular forces.

A particular puzzle is posed by the three-centre iodo⋯nitro interaction, where a series of elegant structures containing symmetrical or nearly symmetrical three-centre interactions have been reported by others; the earlier examples serve as the archetypes for this interaction, which rapidly came to be regarded as a robust supramolecular synthon for crystal engineering (Allen et al., 1994; Thalladi et al., 1996; Masciocchi et al., 1998; George et al., 2004). However, these reports each refer to a single geometrical isomer and these structures all happen to involve molecular components with the substituents at the distal ends, namely the 1:1 adduct of 1,4-diiodobenzene and 1,4-dinitrobenzene (Allen et al., 1994), 4-iodonitrobenzene (Thalladi et al., 1996), 4-iodo-4′-nitrobiphenyl (Masciocchi et al., 1998) and N-4-iodophenyl-N′-4′-nitrophenylurea (George et al., 2004). Likewise, we have observed this interaction in N-(4-iodophenylsulfonyl)-4-nitroaniline and in N-(4′-nitrodophenylsulfonyl)-4-iodoaniline, but not in any of the other isomers in these series; indeed, in the series (A)–(G) noted above (see §1), wherever one or other of the iodo or nitro substituents is in the 2- or 3-positions, three-centre iodo⋯nitro interactions are absent. Consistent with these observations, in 2,4,6-trinitro­iodo­benzene (picryl iodide), a three-centre interaction is formed by the 4-nitro substituent but not by the other two nitro groups (Weiss et al., 1999), while in 1,2-diiodo-4-nitro-5-(butylamino)benzene, the 1-iodosubstituent participates in a three-centre iodo⋯nitro interaction, while the 2-iodo substituent is involved only in a two-centre iodo⋯nitro interaction (Senskey et al., 1995). Hence, it may be that the initial acceptance of the three-centre iodo⋯nitro synthon owes less to its intrinsic utility than to the chance selection of the isomeric forms of the compounds used in the initial studies. On the other hand, there is a three-centre iodo⋯nitro interaction in N-(4-iodophenyl)-3-nitrophthalimide, but there are no iodo⋯nitro interactions at all in N-(4-iodophenyl)-2-nitrophthalimide (Glidewell, Low, Skakle, Wardell & Wardell, 2005). Thus, in substituted aryl systems this synthon appears to behave predictably only for specific isomeric forms, but normally to be absent for the remaining isomeric forms. Reported examples of structures that are described as having been specifically and deliberately engineered by the application of particular supramolecular synthons are often restricted to specific isomer forms of their molecular components, sometimes to a single isomer; in some of these cases there must arise at least a suspicion of an element of post hoc rationalization as opposed to reliable supramolecular design.

The difficulty of structure prediction appears to be entirely characteristic of the crystal structures of molecular compounds where all of the intermolecular forces are comparatively weak, but of comparable magnitudes to the rotational energy barriers associated with single bonds, so that the molecular conformations are a direct reflection of the intermolecular interactions. For this reason alone, molecular conformations computed for isolated molecules are unlikely ever to reproduce the conformations observed experimentally in the crystalline state. More disturbing is the fact that, to date, attempts to make computed predictions of the crystal and molecular structures of even rather simple compounds have met with only limited success (Lommerse et al., 2000; Motherwell et al., 2002; Day et al., 2005). Compounds whose molecules contain internal degrees of freedom, such as rotations about single bonds, particularly where aryl rings are connected to a semi-rigid unit, as in the examples discussed here, seem to pose particular difficulty, possibly associated with the delicate interplay of intramolecular and intermolecular forces.

Supporting information

S1. Comment

In full text version

S2. Experimental

In full text version

S3. Refinement

In full text version

Computing details

Data collection: COLLECT (Hooft, 1999) for (II), (III), (IV), (V), (VI); Bruker APEX2 (Bruker, 2003) for (IX). Cell refinement: DENZO (Otwinowski & Minor, 1997) & COLLECT for (II), (III), (IV), (V), (VI); Bruker APEX2 for (IX). Data reduction: DENZO & COLLECT) for (II), (III), (IV), (V), (VI); Bruker SAINT (Bruker, 2001) for (IX). For all compounds, program(s) used to solve structure: OSCAIL (McArdle, 2003) & SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL & SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures

In full text version

(II) N-(2-iodophenyl)-3-nitrobenzamide

Crystal data

C13H9IN2O3	F(000) = 712
Mr = 368.12	Dx = 1.908 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2942 reflections
a = 13.1804 (3) Å	θ = 3.1–27.6°
b = 7.5099 (2) Å	µ = 2.50 mm^−1
c = 13.8849 (3) Å	T = 120 K
β = 111.1634 (12)°	Plate, colourless
V = 1281.68 (5) Å^3	0.50 × 0.10 × 0.02 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2942 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2549 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 9.091 pixels mm^-1	θmax = 27.6°, θmin = 3.1°
ϕ & ω scans	h = −17→17
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −8→9
Tmin = 0.368, Tmax = 0.952	l = −18→17
15482 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.062	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0327P)^2 + 0.5883P] where P = (Fo^2 + 2Fc^2)/3
2942 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.58 e Å^−3
0 restraints	Δρmin = −0.98 e Å^−3

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

	x	y	z	Uiso*/Ueq
C11	0.34050 (18)	0.3979 (3)	0.22656 (17)	0.0165 (5)
C12	0.2645 (2)	0.3309 (3)	0.26521 (19)	0.0181 (5)
C13	0.1560 (2)	0.3293 (3)	0.2003 (2)	0.0203 (5)
C14	0.12062 (19)	0.3921 (3)	0.09994 (18)	0.0240 (6)
C15	0.1966 (2)	0.4630 (3)	0.06389 (19)	0.0243 (6)
C16	0.3064 (2)	0.4653 (3)	0.12638 (19)	0.0212 (5)
C17	0.45825 (19)	0.3785 (3)	0.29447 (17)	0.0160 (5)
O17	0.48528 (14)	0.2787 (2)	0.36966 (13)	0.0192 (4)
N1	0.53075 (16)	0.4677 (3)	0.26480 (15)	0.0172 (4)
C21	0.64506 (18)	0.4398 (3)	0.31075 (18)	0.0159 (5)
C22	0.70234 (19)	0.3733 (3)	0.25189 (18)	0.0182 (5)
C23	0.8148 (2)	0.3501 (3)	0.2958 (2)	0.0228 (5)
C24	0.86881 (19)	0.3922 (4)	0.3987 (2)	0.0263 (6)
C25	0.8122 (2)	0.4585 (3)	0.4580 (2)	0.0256 (6)
C26	0.7005 (2)	0.4836 (3)	0.41364 (19)	0.0211 (5)
N13	0.07543 (18)	0.2512 (3)	0.23890 (18)	0.0274 (5)
O31	−0.01542 (16)	0.2189 (3)	0.17566 (17)	0.0407 (6)
O32	0.10257 (17)	0.2218 (3)	0.33156 (17)	0.0395 (5)
I22	0.619735 (13)	0.30348 (2)	0.096580 (11)	0.02094 (7)
H12	0.2862	0.2874	0.3340	0.022*
H14	0.0459	0.3866	0.0570	0.029*
H15	0.1739	0.5106	−0.0040	0.029*
H16	0.3584	0.5130	0.1005	0.025*
H1	0.5103	0.5312	0.2077	0.021*
H23	0.8539	0.3058	0.2553	0.027*
H24	0.9453	0.3755	0.4290	0.032*
H25	0.8498	0.4867	0.5287	0.031*
H26	0.6618	0.5309	0.4538	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0178 (11)	0.0154 (11)	0.0155 (11)	0.0022 (9)	0.0049 (9)	−0.0025 (9)
C12	0.0206 (12)	0.0184 (11)	0.0151 (12)	0.0007 (9)	0.0061 (10)	−0.0029 (9)
C13	0.0194 (12)	0.0177 (12)	0.0246 (14)	−0.0002 (9)	0.0090 (11)	−0.0030 (9)
C14	0.0200 (12)	0.0221 (14)	0.0230 (14)	0.0029 (10)	−0.0006 (11)	−0.0025 (10)
C15	0.0277 (13)	0.0230 (12)	0.0175 (13)	0.0028 (10)	0.0025 (10)	0.0032 (10)
C16	0.0251 (13)	0.0186 (12)	0.0189 (12)	0.0005 (9)	0.0066 (10)	0.0017 (9)
C17	0.0214 (12)	0.0146 (11)	0.0121 (11)	0.0003 (9)	0.0060 (9)	−0.0041 (9)
O17	0.0198 (9)	0.0214 (9)	0.0146 (9)	−0.0011 (7)	0.0042 (7)	0.0039 (7)
N1	0.0179 (9)	0.0199 (10)	0.0141 (10)	0.0026 (8)	0.0063 (8)	0.0049 (8)
C21	0.0190 (11)	0.0133 (11)	0.0155 (11)	−0.0010 (8)	0.0062 (9)	0.0027 (8)
C22	0.0224 (12)	0.0169 (11)	0.0150 (11)	−0.0005 (9)	0.0065 (10)	0.0026 (9)
C23	0.0209 (12)	0.0210 (12)	0.0288 (14)	0.0004 (10)	0.0119 (11)	0.0037 (10)
C24	0.0182 (12)	0.0242 (14)	0.0320 (15)	−0.0030 (10)	0.0037 (11)	0.0058 (11)
C25	0.0248 (13)	0.0250 (13)	0.0205 (13)	−0.0049 (10)	0.0004 (11)	0.0020 (10)
C26	0.0260 (12)	0.0207 (12)	0.0184 (12)	−0.0040 (10)	0.0104 (10)	0.0001 (9)
N13	0.0199 (11)	0.0346 (11)	0.0303 (14)	0.0004 (10)	0.0121 (10)	−0.0049 (10)
O31	0.0157 (10)	0.0685 (16)	0.0367 (13)	−0.0086 (9)	0.0079 (9)	−0.0122 (10)
O32	0.0287 (11)	0.0626 (15)	0.0294 (12)	−0.0065 (10)	0.0132 (9)	0.0041 (10)
I22	0.02866 (11)	0.02113 (10)	0.01452 (11)	0.00124 (6)	0.00959 (8)	0.00036 (6)

Geometric parameters (Å, º)

C11—C12	1.390 (3)	N1—H1	0.88
C11—C16	1.393 (3)	C21—C26	1.389 (3)
C11—C17	1.504 (3)	C21—C22	1.390 (3)
C12—C13	1.389 (3)	C22—C23	1.395 (3)
C12—H12	0.95	C22—I22	2.101 (2)
C13—C14	1.383 (4)	C23—C24	1.383 (4)
C13—N13	1.473 (3)	C23—H23	0.95
C14—C15	1.377 (4)	C24—C25	1.389 (4)
C14—H14	0.95	C24—H24	0.95
C15—C16	1.394 (3)	C25—C26	1.389 (4)
C15—H15	0.95	C25—H25	0.95
C16—H16	0.95	C26—H26	0.95
C17—O17	1.229 (3)	N13—O32	1.225 (3)
C17—N1	1.348 (3)	N13—O31	1.227 (3)
N1—C21	1.424 (3)
C12—C11—C16	120.0 (2)	C21—N1—H1	114.5
C12—C11—C17	116.5 (2)	C26—C21—C22	119.6 (2)
C16—C11—C17	123.3 (2)	C26—C21—N1	120.3 (2)
C13—C12—C11	118.0 (2)	C22—C21—N1	120.1 (2)
C13—C12—H12	121.0	C21—C22—C23	120.3 (2)
C11—C12—H12	121.0	C21—C22—I22	120.19 (17)
C14—C13—C12	123.0 (2)	C23—C22—I22	119.51 (19)
C14—C13—N13	118.5 (2)	C24—C23—C22	119.5 (2)
C12—C13—N13	118.4 (2)	C24—C23—H23	120.2
C15—C14—C13	118.3 (2)	C22—C23—H23	120.2
C15—C14—H14	120.9	C23—C24—C25	120.5 (2)
C13—C14—H14	120.9	C23—C24—H24	119.7
C14—C15—C16	120.4 (2)	C25—C24—H24	119.7
C14—C15—H15	119.8	C24—C25—C26	119.7 (2)
C16—C15—H15	119.8	C24—C25—H25	120.1
C11—C16—C15	120.3 (2)	C26—C25—H25	120.1
C11—C16—H16	119.8	C25—C26—C21	120.3 (2)
C15—C16—H16	119.8	C25—C26—H26	119.9
O17—C17—N1	122.9 (2)	C21—C26—H26	119.9
O17—C17—C11	120.6 (2)	O32—N13—O31	123.8 (2)
N1—C17—C11	116.4 (2)	O32—N13—C13	118.6 (2)
C17—N1—C21	122.84 (19)	O31—N13—C13	117.6 (2)
C17—N1—H1	121.6
C16—C11—C12—C13	1.7 (3)	C17—N1—C21—C22	116.5 (3)
C17—C11—C12—C13	−173.2 (2)	C26—C21—C22—C23	0.2 (3)
C11—C12—C13—C14	−0.4 (4)	N1—C21—C22—C23	178.3 (2)
C11—C12—C13—N13	177.3 (2)	C26—C21—C22—I22	179.28 (17)
C12—C13—C14—C15	−1.5 (4)	N1—C21—C22—I22	−2.6 (3)
N13—C13—C14—C15	−179.2 (2)	C21—C22—C23—C24	0.6 (4)
C13—C14—C15—C16	2.1 (4)	I22—C22—C23—C24	−178.50 (18)
C12—C11—C16—C15	−1.1 (4)	C22—C23—C24—C25	−0.6 (4)
C17—C11—C16—C15	173.5 (2)	C23—C24—C25—C26	−0.3 (4)
C14—C15—C16—C11	−0.8 (4)	C24—C25—C26—C21	1.1 (4)
C12—C11—C17—O17	13.8 (3)	C22—C21—C26—C25	−1.0 (3)
C16—C11—C17—O17	−161.0 (2)	N1—C21—C26—C25	−179.1 (2)
C12—C11—C17—N1	−169.8 (2)	C14—C13—N13—O32	−168.4 (2)
C16—C11—C17—N1	15.5 (3)	C12—C13—N13—O32	13.8 (4)
O17—C17—N1—C21	7.1 (3)	C14—C13—N13—O31	11.7 (4)
C11—C17—N1—C21	−169.3 (2)	C12—C13—N13—O31	−166.1 (2)
C17—N1—C21—C26	−65.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O17^i	0.88	2.16	2.950 (3)	149
C23—H23···O31^ii	0.95	2.45	3.385 (4)	169

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y, z.

(III) N-(2-iodophenyl)-4-nitrobenzamide

Crystal data

C13H9IN2O3	F(000) = 356
Mr = 368.12	Dx = 1.957 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2767 reflections
a = 10.0528 (3) Å	θ = 3.2–27.5°
b = 4.8703 (10) Å	µ = 2.57 mm^−1
c = 13.5719 (3) Å	T = 120 K
β = 109.9452 (17)°	Plate, brown
V = 624.63 (13) Å^3	0.42 × 0.30 × 0.08 mm
Z = 2

Data collection

Bruker-Nonius KappaCCD diffractometer	2767 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2624 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ϕ & ω scans	h = −13→13
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −6→6
Tmin = 0.412, Tmax = 0.821	l = −17→17
10157 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.019	w = 1/[σ^2(Fo^2) + (0.022P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.048	(Δ/σ)max < 0.001
S = 1.21	Δρmax = 0.67 e Å^−3
2767 reflections	Δρmin = −0.62 e Å^−3
173 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0225 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1328 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.006 (17)

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

	x	y	z	Uiso*/Ueq
C11	0.5752 (3)	0.3044 (6)	0.4647 (2)	0.0166 (6)
C12	0.6262 (3)	0.0947 (5)	0.5369 (2)	0.0178 (6)
C13	0.5580 (3)	0.0257 (6)	0.6070 (2)	0.0203 (6)
C14	0.4401 (3)	0.1752 (6)	0.6040 (2)	0.0193 (6)
C15	0.3863 (4)	0.3834 (6)	0.5336 (3)	0.0219 (7)
C16	0.4536 (3)	0.4493 (6)	0.4629 (2)	0.0227 (6)
C17	0.6533 (3)	0.3998 (5)	0.3944 (3)	0.0162 (6)
O17	0.6439 (3)	0.6401 (3)	0.3643 (2)	0.0222 (5)
N1	0.7377 (3)	0.2097 (5)	0.37238 (19)	0.0170 (5)
C21	0.8439 (3)	0.2622 (5)	0.3288 (2)	0.0174 (5)
C22	0.9731 (3)	0.1242 (5)	0.3667 (3)	0.0191 (6)
C23	1.0798 (4)	0.1711 (6)	0.3246 (3)	0.0275 (7)
C24	1.0584 (4)	0.3658 (6)	0.2466 (3)	0.0326 (9)
C25	0.9320 (4)	0.5056 (7)	0.2088 (3)	0.0299 (7)
C26	0.8237 (3)	0.4548 (6)	0.2474 (2)	0.0243 (6)
N14	0.3713 (3)	0.1070 (5)	0.6813 (2)	0.0242 (6)
O41	0.4000 (3)	−0.1124 (4)	0.7272 (2)	0.0316 (6)
O42	0.2887 (3)	0.2714 (6)	0.6949 (2)	0.0413 (6)
I22	1.01765 (2)	−0.13097 (3)	0.49856 (2)	0.02465 (8)
H12	0.7088	−0.0029	0.5385	0.021*
H13	0.5917	−0.1203	0.6556	0.024*
H15	0.3043	0.4809	0.5332	0.026*
H16	0.4175	0.5922	0.4133	0.027*
H1	0.7243	0.0343	0.3813	0.020*
H23	1.1659	0.0708	0.3493	0.033*
H24	1.1314	0.4033	0.2188	0.039*
H25	0.9190	0.6393	0.1554	0.036*
H26	0.7362	0.5491	0.2192	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0155 (15)	0.0154 (11)	0.0191 (15)	−0.0022 (12)	0.0060 (12)	−0.0037 (11)
C12	0.0159 (14)	0.0184 (13)	0.0186 (15)	0.0033 (10)	0.0053 (12)	−0.0011 (10)
C13	0.0198 (14)	0.0210 (13)	0.0197 (14)	0.0018 (11)	0.0059 (11)	0.0005 (11)
C14	0.0155 (15)	0.0253 (14)	0.0200 (16)	−0.0037 (11)	0.0097 (12)	−0.0076 (11)
C15	0.0164 (18)	0.0217 (16)	0.030 (2)	0.0024 (10)	0.0104 (15)	−0.0065 (10)
C16	0.0204 (15)	0.0183 (13)	0.0298 (16)	0.0044 (12)	0.0093 (12)	0.0018 (12)
C17	0.0142 (14)	0.0139 (13)	0.0191 (17)	−0.0014 (9)	0.0038 (12)	−0.0015 (9)
O17	0.0265 (13)	0.0120 (10)	0.0301 (13)	0.0017 (7)	0.0120 (10)	0.0010 (7)
N1	0.0210 (13)	0.0117 (10)	0.0207 (13)	−0.0007 (10)	0.0103 (10)	0.0008 (10)
C21	0.0221 (15)	0.0119 (13)	0.0188 (14)	−0.0050 (11)	0.0079 (11)	−0.0033 (10)
C22	0.0189 (15)	0.0194 (14)	0.0195 (16)	−0.0046 (10)	0.0070 (12)	−0.0056 (9)
C23	0.0209 (16)	0.0362 (18)	0.0272 (19)	−0.0065 (13)	0.0105 (13)	−0.0131 (12)
C24	0.036 (2)	0.039 (2)	0.032 (2)	−0.0234 (15)	0.0233 (18)	−0.0142 (13)
C25	0.045 (2)	0.0234 (16)	0.0261 (17)	−0.0110 (14)	0.0188 (15)	−0.0024 (13)
C26	0.0358 (18)	0.0173 (13)	0.0203 (15)	−0.0044 (13)	0.0101 (13)	−0.0018 (11)
N14	0.0184 (14)	0.0339 (16)	0.0231 (15)	−0.0065 (11)	0.0110 (12)	−0.0102 (11)
O41	0.0297 (14)	0.0405 (14)	0.0285 (14)	0.0006 (9)	0.0150 (11)	0.0077 (9)
O42	0.0415 (16)	0.0378 (14)	0.0598 (17)	0.0025 (12)	0.0368 (14)	−0.0075 (13)
I22	0.02063 (10)	0.02722 (11)	0.02339 (11)	0.00400 (9)	0.00399 (6)	0.00105 (9)

Geometric parameters (Å, º)

C11—C12	1.387 (4)	N1—H1	0.88
C11—C16	1.404 (4)	C21—C22	1.395 (4)
C11—C17	1.501 (4)	C21—C26	1.411 (4)
C12—C13	1.390 (4)	C22—C23	1.395 (5)
C12—H12	0.95	C22—I22	2.097 (3)
C13—C14	1.380 (4)	C23—C24	1.383 (5)
C13—H13	0.95	C23—H23	0.95
C14—C15	1.372 (5)	C24—C25	1.377 (6)
C14—N14	1.478 (4)	C24—H24	0.95
C15—C16	1.387 (5)	C25—C26	1.381 (4)
C15—H15	0.95	C25—H25	0.95
C16—H16	0.95	C26—H26	0.95
C17—O17	1.233 (3)	N14—O42	1.212 (4)
C17—N1	1.356 (4)	N14—O41	1.221 (3)
N1—C21	1.410 (4)
C12—C11—C16	119.5 (3)	C21—N1—H1	114.0
C12—C11—C17	122.0 (3)	C22—C21—N1	120.1 (2)
C16—C11—C17	118.3 (3)	C22—C21—C26	118.5 (3)
C11—C12—C13	120.8 (3)	N1—C21—C26	121.5 (3)
C11—C12—H12	119.6	C21—C22—C23	121.2 (3)
C13—C12—H12	119.6	C21—C22—I22	120.1 (2)
C14—C13—C12	118.2 (3)	C23—C22—I22	118.4 (2)
C14—C13—H13	120.9	C24—C23—C22	119.1 (3)
C12—C13—H13	120.9	C24—C23—H23	120.5
C15—C14—C13	122.7 (3)	C22—C23—H23	120.5
C15—C14—N14	119.5 (3)	C25—C24—C23	120.4 (3)
C13—C14—N14	117.8 (3)	C25—C24—H24	119.8
C14—C15—C16	118.9 (3)	C23—C24—H24	119.8
C14—C15—H15	120.5	C24—C25—C26	121.1 (3)
C16—C15—H15	120.5	C24—C25—H25	119.4
C15—C16—C11	119.9 (3)	C26—C25—H25	119.4
C15—C16—H16	120.1	C25—C26—C21	119.6 (3)
C11—C16—H16	120.1	C25—C26—H26	120.2
O17—C17—N1	123.9 (3)	C21—C26—H26	120.2
O17—C17—C11	120.5 (3)	O42—N14—O41	123.7 (3)
N1—C17—C11	115.5 (2)	O42—N14—C14	118.1 (3)
C17—N1—C21	126.1 (2)	O41—N14—C14	118.2 (2)
C17—N1—H1	119.7
C16—C11—C12—C13	0.3 (4)	C17—N1—C21—C26	−40.7 (4)
C17—C11—C12—C13	174.6 (3)	N1—C21—C22—C23	179.7 (3)
C11—C12—C13—C14	−1.3 (4)	C26—C21—C22—C23	−0.9 (4)
C12—C13—C14—C15	1.5 (4)	N1—C21—C22—I22	−6.3 (3)
C12—C13—C14—N14	−177.8 (3)	C26—C21—C22—I22	173.15 (19)
C13—C14—C15—C16	−0.7 (5)	C21—C22—C23—C24	2.4 (4)
N14—C14—C15—C16	178.6 (3)	I22—C22—C23—C24	−171.7 (2)
C14—C15—C16—C11	−0.4 (5)	C22—C23—C24—C25	−1.9 (5)
C12—C11—C16—C15	0.5 (4)	C23—C24—C25—C26	−0.3 (5)
C17—C11—C16—C15	−174.0 (3)	C24—C25—C26—C21	1.8 (5)
C12—C11—C17—O17	−150.0 (3)	C22—C21—C26—C25	−1.2 (4)
C16—C11—C17—O17	24.4 (4)	N1—C21—C26—C25	178.2 (3)
C12—C11—C17—N1	26.8 (4)	C15—C14—N14—O42	−15.2 (4)
C16—C11—C17—N1	−158.8 (3)	C13—C14—N14—O42	164.2 (3)
O17—C17—N1—C21	11.6 (5)	C15—C14—N14—O41	164.2 (3)
C11—C17—N1—C21	−165.0 (3)	C13—C14—N14—O41	−16.4 (4)
C17—N1—C21—C22	138.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O17^i	0.88	2.06	2.920 (3)	164
C24—H24···O42^ii	0.95	2.34	3.175 (4)	147
C26—H26···Cg1^iii	0.95	2.95	3.800 (3)	149

Symmetry codes: (i) x, y−1, z; (ii) x+1, −y+1, z−1/2; (iii) x, −y+1, z−1/2.

(IV) N-(3-iodophenyl)-2-nitrobenzamide

Crystal data

C13H9IN2O3	F(000) = 712
Mr = 368.12	Dx = 1.928 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5672 reflections
a = 11.0552 (3) Å	θ = 3.2–27.5°
b = 8.9521 (2) Å	µ = 2.53 mm^−1
c = 12.8921 (3) Å	T = 120 K
β = 96.3899 (10)°	Plate, colourless
V = 1267.97 (5) Å^3	0.40 × 0.20 × 0.08 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	5672 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	5506 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ϕ & ω scans	h = −14→12
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −11→11
Tmin = 0.431, Tmax = 0.823	l = −16→16
16241 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.020	w = 1/[σ^2(Fo^2) + (0.0177P)^2 + 0.1391P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.046	(Δ/σ)max = 0.001
S = 1.11	Δρmax = 0.66 e Å^−3
5672 reflections	Δρmin = −0.80 e Å^−3
344 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0075 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2565 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.008 (11)

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

	x	y	z	Uiso*/Ueq
C11	0.5361 (2)	0.0339 (3)	0.3889 (2)	0.0140 (6)
C12	0.6294 (2)	−0.0495 (3)	0.3519 (2)	0.0171 (6)
N12	0.7028 (2)	−0.1510 (3)	0.42213 (19)	0.0232 (5)
O121	0.6803 (2)	−0.1627 (2)	0.51257 (16)	0.0269 (5)
O122	0.7834 (3)	−0.2232 (4)	0.38748 (19)	0.0673 (10)
C13	0.6588 (3)	−0.0378 (3)	0.2506 (2)	0.0208 (6)
C14	0.5935 (3)	0.0629 (3)	0.1842 (2)	0.0234 (7)
C15	0.5032 (3)	0.1482 (3)	0.2182 (2)	0.0241 (7)
C16	0.4744 (3)	0.1339 (3)	0.3209 (2)	0.0196 (6)
C17	0.4965 (3)	0.0170 (3)	0.4971 (2)	0.0147 (6)
O17	0.41838 (18)	−0.0745 (2)	0.51331 (15)	0.0180 (4)
N11	0.5480 (2)	0.1177 (2)	0.56613 (16)	0.0170 (5)
C21	0.5354 (2)	0.1321 (3)	0.6736 (2)	0.0155 (6)
C22	0.4459 (2)	0.0584 (3)	0.7217 (2)	0.0165 (6)
C23	0.4390 (3)	0.0853 (3)	0.8276 (2)	0.0166 (6)
I23	0.300637 (19)	−0.021189 (19)	0.899446 (13)	0.02235 (6)
C24	0.5187 (3)	0.1804 (3)	0.8850 (2)	0.0202 (6)
C25	0.6085 (3)	0.2506 (3)	0.8364 (2)	0.0212 (7)
C26	0.6169 (3)	0.2271 (3)	0.7309 (2)	0.0168 (6)
C31	0.0663 (3)	0.6213 (3)	0.1153 (2)	0.0149 (6)
C32	0.1448 (2)	0.5035 (3)	0.1487 (2)	0.0157 (6)
N32	0.2162 (2)	0.4294 (3)	0.07455 (19)	0.0216 (5)
O321	0.2260 (2)	0.4905 (3)	−0.00874 (15)	0.0295 (5)
O322	0.2637 (2)	0.3094 (3)	0.09954 (18)	0.0433 (6)
C33	0.1612 (3)	0.4573 (3)	0.2516 (2)	0.0199 (6)
C34	0.0992 (3)	0.5298 (3)	0.3236 (2)	0.0232 (7)
C35	0.0238 (3)	0.6478 (4)	0.2939 (2)	0.0257 (7)
C36	0.0063 (3)	0.6926 (3)	0.1900 (2)	0.0201 (6)
C37	0.0462 (3)	0.6776 (3)	0.0046 (2)	0.0146 (6)
O37	0.08278 (17)	0.8034 (2)	−0.01673 (14)	0.0199 (4)
N31	−0.0173 (2)	0.5866 (3)	−0.06381 (16)	0.0169 (5)
C41	−0.0326 (2)	0.6045 (3)	−0.1738 (2)	0.0151 (5)
C42	0.0577 (2)	0.6711 (3)	−0.22596 (19)	0.0141 (5)
C43	0.0390 (2)	0.6796 (3)	−0.3340 (2)	0.0156 (5)
I43	0.171754 (17)	0.788540 (17)	−0.411901 (13)	0.01903 (6)
C44	−0.0636 (3)	0.6223 (3)	−0.3909 (2)	0.0184 (6)
C45	−0.1510 (3)	0.5536 (3)	−0.3375 (2)	0.0211 (7)
C46	−0.1361 (3)	0.5457 (3)	−0.2301 (2)	0.0190 (6)
H13	0.7217	−0.0970	0.2272	0.025*
H14	0.6119	0.0727	0.1142	0.028*
H15	0.4598	0.2172	0.1721	0.029*
H16	0.4117	0.1939	0.3440	0.023*
H11	0.5961	0.1835	0.5408	0.020*
H22	0.3910	−0.0085	0.6835	0.020*
H24	0.5120	0.1974	0.9569	0.024*
H25	0.6647	0.3152	0.8753	0.025*
H26	0.6785	0.2761	0.6979	0.020*
H33	0.2145	0.3767	0.2722	0.024*
H34	0.1087	0.4979	0.3943	0.028*
H35	−0.0166	0.6990	0.3446	0.031*
H36	−0.0474	0.7730	0.1700	0.024*
H31	−0.0525	0.5089	−0.0382	0.020*
H42	0.1299	0.7095	−0.1885	0.017*
H44	−0.0743	0.6295	−0.4649	0.022*
H45	−0.2216	0.5119	−0.3753	0.025*
H46	−0.1969	0.4997	−0.1944	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0146 (15)	0.0140 (12)	0.0134 (13)	−0.0027 (10)	0.0020 (11)	−0.0012 (10)
C12	0.0157 (14)	0.0190 (14)	0.0161 (13)	0.0000 (10)	−0.0014 (11)	0.0002 (10)
N12	0.0177 (14)	0.0325 (13)	0.0196 (13)	0.0068 (11)	0.0025 (10)	0.0037 (11)
O121	0.0282 (13)	0.0332 (12)	0.0204 (11)	0.0074 (9)	0.0066 (9)	0.0109 (9)
O122	0.0556 (19)	0.111 (3)	0.0368 (15)	0.062 (2)	0.0144 (14)	0.0134 (17)
C13	0.0202 (15)	0.0269 (16)	0.0165 (13)	0.0008 (12)	0.0079 (11)	−0.0040 (12)
C14	0.0258 (17)	0.0322 (17)	0.0128 (13)	0.0007 (13)	0.0046 (12)	0.0015 (12)
C15	0.0310 (19)	0.0258 (16)	0.0154 (14)	0.0064 (13)	0.0028 (13)	0.0041 (12)
C16	0.0203 (16)	0.0157 (15)	0.0236 (15)	0.0040 (11)	0.0066 (12)	−0.0002 (11)
C17	0.0137 (14)	0.0154 (16)	0.0149 (13)	0.0053 (11)	0.0017 (11)	0.0035 (10)
O17	0.0187 (11)	0.0189 (10)	0.0173 (10)	−0.0051 (8)	0.0060 (8)	−0.0032 (7)
N11	0.0214 (14)	0.0183 (12)	0.0117 (11)	−0.0083 (9)	0.0042 (10)	0.0006 (9)
C21	0.0194 (16)	0.0158 (14)	0.0119 (13)	0.0044 (11)	0.0040 (11)	−0.0008 (10)
C22	0.0220 (16)	0.0145 (14)	0.0132 (13)	−0.0038 (11)	0.0034 (11)	−0.0007 (10)
C23	0.0219 (16)	0.0143 (13)	0.0145 (13)	0.0008 (12)	0.0064 (11)	0.0029 (11)
I23	0.02843 (11)	0.02374 (10)	0.01655 (10)	−0.00318 (9)	0.00992 (7)	0.00057 (8)
C24	0.0264 (17)	0.0229 (15)	0.0110 (13)	0.0018 (12)	0.0004 (12)	0.0026 (11)
C25	0.0221 (17)	0.0197 (16)	0.0211 (15)	−0.0060 (11)	−0.0009 (13)	−0.0068 (12)
C26	0.0179 (15)	0.0182 (13)	0.0145 (14)	−0.0037 (11)	0.0026 (12)	0.0004 (11)
C31	0.0148 (14)	0.0162 (14)	0.0136 (12)	−0.0047 (10)	0.0017 (11)	−0.0015 (10)
C32	0.0148 (14)	0.0161 (14)	0.0159 (13)	−0.0034 (11)	−0.0001 (11)	−0.0001 (11)
N32	0.0180 (14)	0.0231 (13)	0.0234 (13)	0.0012 (10)	0.0010 (10)	−0.0020 (10)
O321	0.0309 (13)	0.0389 (13)	0.0207 (11)	0.0116 (11)	0.0110 (9)	0.0060 (11)
O322	0.0540 (17)	0.0332 (13)	0.0439 (14)	0.0267 (12)	0.0111 (12)	0.0099 (11)
C33	0.0203 (16)	0.0174 (15)	0.0207 (14)	−0.0033 (12)	−0.0034 (12)	0.0056 (12)
C34	0.0285 (19)	0.0291 (17)	0.0114 (14)	−0.0115 (14)	−0.0011 (13)	0.0064 (12)
C35	0.0272 (18)	0.0357 (18)	0.0156 (14)	−0.0068 (14)	0.0092 (13)	−0.0035 (12)
C36	0.0204 (16)	0.0209 (15)	0.0196 (14)	−0.0001 (12)	0.0049 (12)	−0.0044 (11)
C37	0.0131 (15)	0.0155 (13)	0.0159 (14)	0.0021 (11)	0.0040 (11)	0.0005 (11)
O37	0.0291 (11)	0.0136 (10)	0.0181 (9)	−0.0028 (9)	0.0070 (8)	−0.0005 (8)
N31	0.0188 (13)	0.0181 (11)	0.0139 (11)	−0.0045 (9)	0.0030 (9)	0.0021 (9)
C41	0.0168 (15)	0.0154 (13)	0.0134 (13)	0.0023 (10)	0.0028 (11)	0.0015 (10)
C42	0.0110 (13)	0.0154 (13)	0.0153 (13)	0.0000 (10)	−0.0012 (10)	−0.0006 (11)
C43	0.0155 (15)	0.0153 (13)	0.0165 (13)	0.0020 (11)	0.0039 (11)	0.0003 (11)
I43	0.02118 (10)	0.02265 (10)	0.01419 (9)	−0.00036 (8)	0.00611 (7)	0.00229 (7)
C44	0.0200 (15)	0.0223 (15)	0.0123 (13)	0.0016 (11)	−0.0012 (11)	0.0006 (11)
C45	0.0170 (16)	0.0249 (15)	0.0205 (15)	−0.0045 (12)	−0.0022 (13)	−0.0037 (12)
C46	0.0173 (16)	0.0193 (14)	0.0209 (15)	−0.0022 (12)	0.0051 (12)	0.0022 (11)

Geometric parameters (Å, º)

C11—C16	1.379 (4)	C31—C36	1.384 (4)
C11—C12	1.400 (4)	C31—C32	1.402 (4)
C11—C17	1.516 (4)	C31—C37	1.507 (4)
C12—C13	1.383 (4)	C32—C33	1.382 (4)
C12—N12	1.463 (3)	C32—N32	1.465 (4)
N12—O121	1.224 (3)	N32—O321	1.220 (3)
N12—O122	1.224 (3)	N32—O322	1.223 (3)
C13—C14	1.389 (4)	C33—C34	1.376 (4)
C13—H13	0.95	C33—H33	0.95
C14—C15	1.368 (4)	C34—C35	1.373 (4)
C14—H14	0.95	C34—H34	0.95
C15—C16	1.402 (4)	C35—C36	1.392 (4)
C15—H15	0.95	C35—H35	0.95
C16—H16	0.95	C36—H36	0.95
C17—O17	1.225 (4)	C37—O37	1.238 (3)
C17—N11	1.347 (4)	C37—N31	1.340 (4)
N11—C21	1.414 (3)	N31—C41	1.418 (3)
N11—H11	0.88	N31—H31	0.88
C21—C26	1.390 (4)	C41—C46	1.389 (4)
C21—C22	1.391 (4)	C41—C42	1.398 (4)
C22—C23	1.397 (3)	C42—C43	1.387 (3)
C22—H22	0.95	C42—H42	0.95
C23—C24	1.380 (4)	C43—C44	1.379 (4)
C23—I23	2.102 (3)	C43—I43	2.108 (3)
C24—C25	1.383 (4)	C44—C45	1.390 (4)
C24—H24	0.95	C44—H44	0.95
C25—C26	1.389 (4)	C45—C46	1.378 (4)
C25—H25	0.95	C45—H45	0.95
C26—H26	0.95	C46—H46	0.95
C16—C11—C12	117.4 (2)	C36—C31—C32	117.5 (2)
C16—C11—C17	118.5 (2)	C36—C31—C37	118.2 (3)
C12—C11—C17	124.1 (2)	C32—C31—C37	124.3 (2)
C13—C12—C11	122.7 (2)	C33—C32—C31	122.0 (3)
C13—C12—N12	117.3 (2)	C33—C32—N32	117.9 (2)
C11—C12—N12	119.9 (2)	C31—C32—N32	120.0 (2)
O121—N12—O122	122.4 (3)	O321—N32—O322	123.2 (3)
O121—N12—C12	119.1 (2)	O321—N32—C32	118.6 (2)
O122—N12—C12	118.5 (2)	O322—N32—C32	118.2 (2)
C12—C13—C14	118.1 (3)	C34—C33—C32	118.9 (3)
C12—C13—H13	121.0	C34—C33—H33	120.5
C14—C13—H13	121.0	C32—C33—H33	120.5
C15—C14—C13	120.8 (3)	C35—C34—C33	120.5 (3)
C15—C14—H14	119.6	C35—C34—H34	119.8
C13—C14—H14	119.6	C33—C34—H34	119.8
C14—C15—C16	120.2 (3)	C34—C35—C36	120.3 (3)
C14—C15—H15	119.9	C34—C35—H35	119.8
C16—C15—H15	119.9	C36—C35—H35	119.8
C11—C16—C15	120.8 (3)	C31—C36—C35	120.7 (3)
C11—C16—H16	119.6	C31—C36—H36	119.7
C15—C16—H16	119.6	C35—C36—H36	119.7
O17—C17—N11	126.1 (3)	O37—C37—N31	124.6 (2)
O17—C17—C11	120.3 (3)	O37—C37—C31	119.8 (2)
N11—C17—C11	113.4 (2)	N31—C37—C31	115.6 (2)
C17—N11—C21	128.9 (2)	C37—N31—C41	125.8 (2)
C17—N11—H11	115.5	C37—N31—H31	117.1
C21—N11—H11	115.5	C41—N31—H31	117.1
C26—C21—C22	120.3 (2)	C46—C41—C42	120.1 (2)
C26—C21—N11	116.7 (2)	C46—C41—N31	118.7 (2)
C22—C21—N11	123.1 (2)	C42—C41—N31	121.1 (2)
C21—C22—C23	118.2 (2)	C43—C42—C41	118.2 (2)
C21—C22—H22	120.9	C43—C42—H42	120.9
C23—C22—H22	120.9	C41—C42—H42	120.9
C24—C23—C22	121.9 (3)	C44—C43—C42	122.4 (3)
C24—C23—I23	119.75 (19)	C44—C43—I43	119.56 (19)
C22—C23—I23	118.3 (2)	C42—C43—I43	118.0 (2)
C23—C24—C25	119.0 (3)	C43—C44—C45	118.4 (3)
C23—C24—H24	120.5	C43—C44—H44	120.8
C25—C24—H24	120.5	C45—C44—H44	120.8
C24—C25—C26	120.3 (3)	C46—C45—C44	120.6 (3)
C24—C25—H25	119.9	C46—C45—H45	119.7
C26—C25—H25	119.9	C44—C45—H45	119.7
C25—C26—C21	120.2 (3)	C45—C46—C41	120.3 (3)
C25—C26—H26	119.9	C45—C46—H46	119.8
C21—C26—H26	119.9	C41—C46—H46	119.8
C16—C11—C12—C13	−1.8 (4)	C36—C31—C32—C33	1.0 (4)
C17—C11—C12—C13	176.2 (3)	C37—C31—C32—C33	179.2 (3)
C16—C11—C12—N12	176.4 (2)	C36—C31—C32—N32	−176.5 (2)
C17—C11—C12—N12	−5.7 (4)	C37—C31—C32—N32	1.7 (4)
C13—C12—N12—O121	179.1 (3)	C33—C32—N32—O321	−162.4 (3)
C11—C12—N12—O121	0.9 (4)	C31—C32—N32—O321	15.2 (4)
C13—C12—N12—O122	−2.2 (4)	C33—C32—N32—O322	17.2 (4)
C11—C12—N12—O122	179.6 (3)	C31—C32—N32—O322	−165.2 (3)
C11—C12—C13—C14	1.0 (4)	C31—C32—C33—C34	−0.4 (4)
N12—C12—C13—C14	−177.2 (3)	N32—C32—C33—C34	177.1 (3)
C12—C13—C14—C15	0.2 (4)	C32—C33—C34—C35	−1.1 (4)
C13—C14—C15—C16	−0.5 (5)	C33—C34—C35—C36	2.0 (5)
C12—C11—C16—C15	1.4 (4)	C32—C31—C36—C35	−0.1 (4)
C17—C11—C16—C15	−176.7 (3)	C37—C31—C36—C35	−178.4 (3)
C14—C15—C16—C11	−0.3 (5)	C34—C35—C36—C31	−1.4 (4)
C16—C11—C17—O17	89.6 (3)	C36—C31—C37—O37	66.4 (4)
C12—C11—C17—O17	−88.4 (4)	C32—C31—C37—O37	−111.8 (3)
C16—C11—C17—N11	−85.6 (3)	C36—C31—C37—N31	−110.4 (3)
C12—C11—C17—N11	96.5 (3)	C32—C31—C37—N31	71.4 (4)
O17—C17—N11—C21	7.4 (5)	O37—C37—N31—C41	13.1 (5)
C11—C17—N11—C21	−177.8 (3)	C31—C37—N31—C41	−170.2 (2)
C17—N11—C21—C26	167.8 (3)	C37—N31—C41—C46	−153.1 (3)
C17—N11—C21—C22	−13.2 (4)	C37—N31—C41—C42	31.1 (4)
C26—C21—C22—C23	1.4 (4)	C46—C41—C42—C43	1.6 (4)
N11—C21—C22—C23	−177.6 (2)	N31—C41—C42—C43	177.4 (2)
C21—C22—C23—C24	−0.9 (4)	C41—C42—C43—C44	−1.3 (4)
C21—C22—C23—I23	178.28 (19)	C41—C42—C43—I43	177.36 (19)
C22—C23—C24—C25	−0.3 (4)	C42—C43—C44—C45	0.0 (4)
I23—C23—C24—C25	−179.4 (2)	I43—C43—C44—C45	−178.7 (2)
C23—C24—C25—C26	0.9 (5)	C43—C44—C45—C46	1.1 (4)
C24—C25—C26—C21	−0.4 (4)	C44—C45—C46—C41	−0.8 (4)
C22—C21—C26—C25	−0.8 (4)	C42—C41—C46—C45	−0.6 (4)
N11—C21—C26—C25	178.2 (3)	N31—C41—C46—C45	−176.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O17^i	0.88	2.28	2.978 (3)	137
N31—H31···O37^ii	0.88	2.01	2.863 (3)	162
C14—H14···O321^iii	0.95	2.48	3.243 (4)	137
C15—H15···O322	0.95	2.41	3.245 (4)	147
C16—H16···O121^i	0.95	2.55	3.415 (3)	151
C35—H35···O122^iv	0.95	2.44	3.251 (4)	143

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x, y−1/2, −z; (iii) −x+1, y−1/2, −z; (iv) x−1, y+1, z.

(V) N-(3-iodophenyl)-3-nitrobenzamide

Crystal data

C13H9IN2O3	F(000) = 712
Mr = 368.12	Dx = 1.933 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2797 reflections
a = 13.8494 (4) Å	θ = 4.1–27.5°
b = 10.0495 (3) Å	µ = 2.54 mm^−1
c = 9.4203 (3) Å	T = 120 K
β = 105.2353 (16)°	Block, brown
V = 1265.03 (7) Å^3	0.46 × 0.34 × 0.16 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2797 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2752 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 4.1°
ϕ & ω scans	h = −17→17
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −13→12
Tmin = 0.376, Tmax = 0.666	l = −12→12
7022 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.018	H-atom parameters constrained
wR(F^2) = 0.053	w = 1/[σ^2(Fo^2) + (0.0227P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.24	(Δ/σ)max < 0.001
2797 reflections	Δρmax = 0.56 e Å^−3
172 parameters	Δρmin = −1.09 e Å^−3
2 restraints	Absolute structure: Flack (1983), 1349 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.013 (17)

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

	x	y	z	Uiso*/Ueq
C11	0.7797 (2)	0.6833 (3)	0.7339 (3)	0.0116 (6)
C12	0.8261 (2)	0.6561 (3)	0.6247 (3)	0.0117 (5)
C13	0.8695 (4)	0.7603 (3)	0.5672 (6)	0.0134 (8)
C14	0.8706 (2)	0.8902 (3)	0.6162 (3)	0.0176 (6)
C15	0.8241 (2)	0.9169 (3)	0.7266 (3)	0.0160 (6)
C16	0.7794 (2)	0.8146 (3)	0.7857 (3)	0.0152 (6)
C17	0.72916 (19)	0.5797 (3)	0.8039 (3)	0.0125 (5)
O17	0.71903 (16)	0.5977 (2)	0.92908 (19)	0.0143 (4)
N1	0.69589 (15)	0.4705 (2)	0.7215 (2)	0.0122 (4)
C21	0.6521 (2)	0.3559 (3)	0.7658 (3)	0.0131 (6)
C22	0.6025 (2)	0.3578 (3)	0.8765 (3)	0.0141 (6)
C23	0.5646 (3)	0.2390 (2)	0.9152 (4)	0.0134 (7)
C24	0.5712 (2)	0.1206 (3)	0.8434 (3)	0.0172 (7)
C25	0.6176 (2)	0.1212 (3)	0.7283 (4)	0.0189 (7)
C26	0.6584 (4)	0.2369 (3)	0.6902 (6)	0.0173 (9)
N13	0.9173 (3)	0.7305 (2)	0.4484 (4)	0.0178 (6)
O31	0.91357 (17)	0.6161 (2)	0.4020 (2)	0.0254 (5)
O32	0.95718 (19)	0.8224 (2)	0.3990 (3)	0.0297 (5)
I23	0.50081 (5)	0.240359 (12)	1.09460 (7)	0.01576 (7)
H12	0.8284	0.5679	0.5895	0.014*
H14	0.9022	0.9588	0.5754	0.021*
H15	0.8228	1.0052	0.7620	0.019*
H16	0.7483	0.8335	0.8621	0.018*
H1	0.7088	0.4646	0.6351	0.015*
H22	0.5946	0.4386	0.9246	0.017*
H24	0.5449	0.0406	0.8717	0.021*
H25	0.6211	0.0414	0.6758	0.023*
H26	0.6907	0.2361	0.6128	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0119 (14)	0.0093 (14)	0.0125 (14)	0.0008 (11)	0.0011 (11)	0.0001 (11)
C12	0.0131 (12)	0.0117 (14)	0.0106 (12)	0.0015 (10)	0.0035 (11)	0.0022 (10)
C13	0.014 (2)	0.0163 (18)	0.012 (2)	0.0029 (10)	0.0072 (18)	0.0003 (11)
C14	0.0189 (15)	0.0138 (14)	0.0204 (14)	−0.0044 (11)	0.0057 (12)	0.0035 (11)
C15	0.0221 (15)	0.0087 (14)	0.0181 (14)	−0.0047 (12)	0.0068 (12)	−0.0010 (11)
C16	0.0191 (15)	0.0123 (15)	0.0145 (15)	0.0001 (12)	0.0048 (13)	−0.0024 (12)
C17	0.0134 (12)	0.0105 (13)	0.0124 (12)	0.0026 (10)	0.0013 (10)	0.0021 (11)
O17	0.0228 (10)	0.0140 (11)	0.0081 (8)	−0.0029 (8)	0.0077 (8)	0.0014 (7)
N1	0.0174 (12)	0.0123 (11)	0.0087 (10)	−0.0031 (9)	0.0067 (9)	0.0001 (8)
C21	0.0151 (15)	0.0123 (14)	0.0109 (13)	0.0007 (11)	0.0017 (11)	0.0020 (10)
C22	0.0156 (15)	0.0125 (14)	0.0144 (15)	0.0005 (11)	0.0041 (12)	0.0008 (11)
C23	0.0116 (18)	0.0179 (17)	0.0123 (18)	−0.0014 (10)	0.0061 (14)	0.0008 (9)
C24	0.0196 (18)	0.0134 (15)	0.0202 (16)	−0.0027 (12)	0.0077 (14)	0.0024 (13)
C25	0.0214 (17)	0.0140 (15)	0.0231 (16)	−0.0017 (12)	0.0088 (13)	−0.0031 (13)
C26	0.028 (3)	0.0145 (17)	0.012 (2)	−0.0006 (12)	0.0097 (19)	0.0016 (12)
N13	0.0184 (16)	0.0208 (14)	0.0174 (16)	0.0051 (11)	0.0102 (13)	0.0042 (11)
O31	0.0309 (13)	0.0216 (13)	0.0295 (13)	−0.0015 (10)	0.0181 (11)	−0.0044 (11)
O32	0.0404 (14)	0.0252 (13)	0.0339 (13)	0.0011 (11)	0.0279 (12)	0.0093 (11)
I23	0.01521 (11)	0.01944 (10)	0.01474 (11)	−0.00027 (18)	0.00768 (7)	0.00355 (17)

Geometric parameters (Å, º)

C11—C12	1.377 (4)	N1—H1	0.88
C11—C16	1.407 (5)	C21—C22	1.392 (4)
C11—C17	1.500 (4)	C21—C26	1.406 (4)
C12—C13	1.386 (4)	C22—C23	1.391 (4)
C12—H12	0.95	C22—H22	0.95
C13—C14	1.383 (4)	C23—C24	1.384 (4)
C13—N13	1.473 (6)	C23—I23	2.103 (4)
C14—C15	1.386 (4)	C24—C25	1.397 (5)
C14—H14	0.95	C24—H24	0.95
C15—C16	1.390 (4)	C25—C26	1.381 (4)
C15—H15	0.95	C25—H25	0.95
C16—H16	0.95	C26—H26	0.95
C17—O17	1.237 (3)	N13—O31	1.226 (3)
C17—N1	1.353 (3)	N13—O32	1.228 (4)
N1—C21	1.415 (3)
C12—C11—C16	119.3 (3)	C21—N1—H1	115.2
C12—C11—C17	123.7 (2)	C22—C21—C26	120.0 (3)
C16—C11—C17	117.1 (2)	C22—C21—N1	123.0 (3)
C11—C12—C13	118.6 (3)	C26—C21—N1	117.0 (3)
C11—C12—H12	120.7	C23—C22—C21	118.6 (3)
C13—C12—H12	120.7	C23—C22—H22	120.7
C14—C13—C12	123.4 (4)	C21—C22—H22	120.7
C14—C13—N13	118.5 (3)	C24—C23—C22	122.2 (4)
C12—C13—N13	118.1 (3)	C24—C23—I23	119.6 (2)
C13—C14—C15	117.8 (3)	C22—C23—I23	118.2 (2)
C13—C14—H14	121.1	C23—C24—C25	118.6 (3)
C15—C14—H14	121.1	C23—C24—H24	120.7
C14—C15—C16	120.1 (3)	C25—C24—H24	120.7
C14—C15—H15	120.0	C26—C25—C24	120.5 (3)
C16—C15—H15	120.0	C26—C25—H25	119.7
C15—C16—C11	120.9 (3)	C24—C25—H25	119.7
C15—C16—H16	119.6	C25—C26—C21	120.0 (4)
C11—C16—H16	119.6	C25—C26—H26	120.0
O17—C17—N1	124.0 (2)	C21—C26—H26	120.0
O17—C17—C11	120.0 (2)	O31—N13—O32	123.4 (3)
N1—C17—C11	116.0 (2)	O31—N13—C13	118.4 (3)
C17—N1—C21	126.7 (2)	O32—N13—C13	118.1 (3)
C17—N1—H1	117.7
C16—C11—C12—C13	−1.3 (4)	C17—N1—C21—C22	25.7 (4)
C17—C11—C12—C13	179.4 (3)	C17—N1—C21—C26	−155.9 (3)
C11—C12—C13—C14	1.5 (6)	C26—C21—C22—C23	3.5 (5)
C11—C12—C13—N13	−178.8 (3)	N1—C21—C22—C23	−178.1 (3)
C12—C13—C14—C15	−1.2 (6)	C21—C22—C23—C24	−2.7 (5)
N13—C13—C14—C15	179.1 (3)	C21—C22—C23—I23	174.8 (2)
C13—C14—C15—C16	0.7 (4)	C22—C23—C24—C25	0.0 (5)
C14—C15—C16—C11	−0.6 (4)	I23—C23—C24—C25	−177.4 (2)
C12—C11—C16—C15	0.9 (4)	C23—C24—C25—C26	1.8 (5)
C17—C11—C16—C15	−179.7 (3)	C24—C25—C26—C21	−1.0 (6)
C12—C11—C17—O17	155.7 (3)	C22—C21—C26—C25	−1.7 (6)
C16—C11—C17—O17	−23.7 (4)	N1—C21—C26—C25	179.7 (4)
C12—C11—C17—N1	−25.2 (4)	C14—C13—N13—O31	−177.8 (4)
C16—C11—C17—N1	155.5 (2)	C12—C13—N13—O31	2.5 (6)
O17—C17—N1—C21	−5.4 (4)	C14—C13—N13—O32	0.8 (6)
C11—C17—N1—C21	175.5 (2)	C12—C13—N13—O32	−178.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O17^i	0.88	2.08	2.937 (2)	165
C12—H12···O17^i	0.95	2.48	3.266 (4)	140
C24—H24···O31^ii	0.95	2.48	3.371 (4)	157
C26—H26···O17^i	0.95	2.51	3.256 (5)	136

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x−1/2, −y+1/2, z+1/2.

(VI) N-(3-iodophenyl)-4-nitrobenzamide

Crystal data

C13H9IN2O3	F(000) = 712
Mr = 368.12	Dx = 1.967 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2843 reflections
a = 7.4798 (2) Å	θ = 3.1–27.6°
b = 14.0889 (7) Å	µ = 2.58 mm^−1
c = 11.8138 (6) Å	T = 120 K
β = 93.259 (3)°	Needle, brown
V = 1242.95 (9) Å^3	0.48 × 0.09 × 0.07 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2843 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2529 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 9.091 pixels mm^-1	θmax = 27.6°, θmin = 3.1°
ϕ & ω scans	h = −9→9
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −18→18
Tmin = 0.370, Tmax = 0.840	l = −14→15
13030 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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.286	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + (0.1676P)^2 + 25.4085P] where P = (Fo^2 + 2Fc^2)/3
2843 reflections	(Δ/σ)max < 0.001
161 parameters	Δρmax = 3.92 e Å^−3
0 restraints	Δρmin = −2.57 e Å^−3

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

	x	y	z	Uiso*/Ueq
C11	0.3258 (15)	0.5880 (7)	0.5948 (9)	0.0106 (14)
C12	0.4060 (16)	0.6008 (8)	0.7037 (9)	0.014 (2)
C13	0.4265 (15)	0.6925 (8)	0.7479 (9)	0.014 (2)
C14	0.3651 (15)	0.7682 (8)	0.6808 (9)	0.012 (2)
N14	0.3894 (13)	0.8652 (7)	0.7271 (8)	0.0131 (18)
O41	0.4817 (12)	0.8751 (6)	0.8151 (7)	0.0200 (18)
O42	0.3173 (15)	0.9308 (6)	0.6748 (7)	0.023 (2)
C15	0.2832 (15)	0.7573 (8)	0.5738 (9)	0.0132 (15)
C16	0.2686 (15)	0.6662 (8)	0.5310 (9)	0.0132 (15)
C17	0.3143 (15)	0.4872 (8)	0.5541 (9)	0.0106 (14)
O17	0.3981 (12)	0.4241 (6)	0.6054 (7)	0.0178 (17)
N1	0.2070 (12)	0.4695 (7)	0.4587 (7)	0.0108 (18)
C21	0.1813 (15)	0.3821 (8)	0.4027 (9)	0.013 (2)
C22	0.2234 (15)	0.2955 (8)	0.4531 (9)	0.011 (2)
C23	0.1860 (15)	0.2123 (8)	0.3906 (9)	0.0106 (19)
I23	0.24533 (11)	0.08091 (5)	0.46912 (6)	0.0189 (3)
C24	0.1113 (17)	0.2132 (9)	0.2805 (9)	0.018 (2)
C25	0.0722 (16)	0.3011 (9)	0.2320 (9)	0.016 (2)
C26	0.1025 (16)	0.3847 (8)	0.2913 (9)	0.016 (2)
H12	0.4464	0.5476	0.7473	0.016*
H13	0.4807	0.7028	0.8215	0.016*
H15	0.2386	0.8103	0.5313	0.016*
H16	0.2182	0.6569	0.4563	0.016*
H1	0.1474	0.5182	0.4292	0.013*
H22	0.2762	0.2925	0.5281	0.013*
H24	0.0878	0.1560	0.2399	0.022*
H25	0.0234	0.3038	0.1560	0.019*
H26	0.0702	0.4438	0.2572	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.010 (3)	0.011 (4)	0.010 (3)	0.002 (3)	0.000 (3)	0.002 (3)
C12	0.017 (5)	0.014 (5)	0.010 (4)	0.000 (4)	−0.002 (4)	−0.004 (4)
C13	0.012 (5)	0.019 (6)	0.010 (4)	0.001 (4)	−0.001 (4)	0.002 (4)
C14	0.011 (5)	0.010 (5)	0.016 (5)	0.001 (4)	0.001 (4)	−0.001 (4)
N14	0.011 (4)	0.016 (5)	0.012 (4)	0.000 (4)	0.002 (3)	−0.003 (3)
O41	0.022 (5)	0.020 (4)	0.017 (4)	−0.001 (4)	−0.006 (3)	−0.006 (3)
O42	0.043 (6)	0.011 (4)	0.016 (4)	0.002 (4)	−0.004 (4)	0.001 (3)
C15	0.016 (4)	0.008 (3)	0.015 (3)	0.005 (3)	−0.005 (3)	0.001 (3)
C16	0.016 (4)	0.008 (3)	0.015 (3)	0.005 (3)	−0.005 (3)	0.001 (3)
C17	0.010 (3)	0.011 (4)	0.010 (3)	0.002 (3)	0.000 (3)	0.002 (3)
O17	0.018 (4)	0.018 (4)	0.015 (4)	0.005 (4)	−0.008 (3)	−0.003 (3)
N1	0.013 (4)	0.008 (4)	0.011 (4)	0.000 (3)	−0.006 (3)	0.001 (3)
C21	0.013 (5)	0.013 (5)	0.013 (5)	0.001 (4)	−0.001 (4)	0.000 (4)
C22	0.014 (5)	0.009 (5)	0.011 (4)	0.001 (4)	−0.001 (4)	−0.001 (4)
C23	0.011 (5)	0.008 (4)	0.012 (4)	0.001 (4)	−0.003 (4)	0.000 (4)
I23	0.0298 (5)	0.0087 (4)	0.0179 (5)	−0.0005 (4)	0.0002 (3)	0.0002 (2)
C24	0.020 (6)	0.021 (6)	0.013 (5)	0.000 (5)	−0.004 (4)	−0.003 (4)
C25	0.014 (5)	0.021 (6)	0.011 (4)	−0.003 (4)	−0.003 (4)	−0.004 (4)
C26	0.018 (6)	0.015 (5)	0.014 (5)	−0.003 (4)	−0.006 (4)	0.001 (4)

Geometric parameters (Å, º)

C11—C16	1.389 (14)	C17—N1	1.369 (13)
C11—C12	1.400 (14)	N1—C21	1.406 (14)
C11—C17	1.501 (15)	N1—H1	0.88
C12—C13	1.398 (16)	C21—C22	1.386 (15)
C12—H12	0.95	C21—C26	1.412 (15)
C13—C14	1.392 (15)	C22—C23	1.406 (14)
C13—H13	0.95	C22—H22	0.95
C14—C15	1.381 (15)	C23—C24	1.385 (14)
C14—N14	1.480 (14)	C23—I23	2.106 (11)
N14—O42	1.220 (13)	C24—C25	1.388 (18)
N14—O41	1.223 (13)	C24—H24	0.95
C15—C16	1.381 (15)	C25—C26	1.383 (16)
C15—H15	0.95	C25—H25	0.95
C16—H16	0.95	C26—H26	0.95
C17—O17	1.227 (14)
C16—C11—C12	119.9 (10)	N1—C17—C11	117.2 (9)
C16—C11—C17	124.5 (10)	C17—N1—C21	127.2 (9)
C12—C11—C17	115.5 (9)	C17—N1—H1	116.4
C13—C12—C11	119.7 (10)	C21—N1—H1	116.4
C13—C12—H12	120.2	C22—C21—N1	123.2 (10)
C11—C12—H12	120.2	C22—C21—C26	119.8 (10)
C14—C13—C12	118.0 (10)	N1—C21—C26	117.0 (10)
C14—C13—H13	121.0	C21—C22—C23	118.3 (10)
C12—C13—H13	121.0	C21—C22—H22	120.8
C15—C14—C13	123.4 (10)	C23—C22—H22	120.8
C15—C14—N14	118.7 (9)	C24—C23—C22	122.9 (10)
C13—C14—N14	117.9 (10)	C24—C23—I23	119.1 (8)
O42—N14—O41	123.8 (10)	C22—C23—I23	118.1 (7)
O42—N14—C14	118.1 (9)	C23—C24—C25	117.4 (11)
O41—N14—C14	118.1 (9)	C23—C24—H24	121.3
C14—C15—C16	117.4 (10)	C25—C24—H24	121.3
C14—C15—H15	121.3	C26—C25—C24	121.7 (10)
C16—C15—H15	121.3	C26—C25—H25	119.1
C15—C16—C11	121.5 (10)	C24—C25—H25	119.1
C15—C16—H16	119.2	C25—C26—C21	119.8 (11)
C11—C16—H16	119.2	C25—C26—H26	120.1
O17—C17—N1	122.3 (10)	C21—C26—H26	120.1
O17—C17—C11	120.5 (10)
C16—C11—C12—C13	0.6 (18)	C16—C11—C17—N1	−14.6 (16)
C17—C11—C12—C13	178.5 (10)	C12—C11—C17—N1	167.6 (10)
C11—C12—C13—C14	0.1 (17)	O17—C17—N1—C21	−3.0 (17)
C12—C13—C14—C15	0.9 (17)	C11—C17—N1—C21	177.2 (10)
C12—C13—C14—N14	−179.1 (10)	C17—N1—C21—C22	18.3 (18)
C15—C14—N14—O42	8.5 (16)	C17—N1—C21—C26	−164.1 (11)
C13—C14—N14—O42	−171.4 (10)	N1—C21—C22—C23	177.7 (10)
C15—C14—N14—O41	−170.9 (11)	C26—C21—C22—C23	0.2 (17)
C13—C14—N14—O41	9.2 (15)	C21—C22—C23—C24	0.9 (17)
C13—C14—C15—C16	−2.5 (18)	C21—C22—C23—I23	−178.7 (8)
N14—C14—C15—C16	177.6 (10)	C22—C23—C24—C25	−0.3 (18)
C14—C15—C16—C11	3.1 (17)	I23—C23—C24—C25	179.3 (8)
C12—C11—C16—C15	−2.2 (18)	C23—C24—C25—C26	−1.4 (18)
C17—C11—C16—C15	−180.0 (11)	C24—C25—C26—C21	2.4 (19)
C16—C11—C17—O17	165.6 (11)	C22—C21—C26—C25	−1.8 (18)
C12—C11—C17—O17	−12.2 (16)	N1—C21—C26—C25	−179.4 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O41^i	0.88	2.33	3.191 (13)	167
C16—H16···O41^i	0.95	2.40	3.291 (14)	155
C24—H24···O17^ii	0.95	2.36	3.192 (15)	147

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+1/2, z−1/2.

(IX) N-(4-iodophenyl)-4-nitrobenzamide

Crystal data

C13H9IN2O3	Z = 4
Mr = 368.12	F(000) = 712
Triclinic, P1	Dx = 1.917 Mg m^−3
Hall symbol: -P 1	Synchrotron radiation, λ = 0.6712 Å
a = 5.1047 (3) Å	Cell parameters from 7348 reflections
b = 15.3015 (9) Å	θ = 2.5–28.7°
c = 16.4806 (9) Å	µ = 2.52 mm^−1
α = 95.356 (2)°	T = 120 K
β = 95.498 (2)°	Needle, colourless
γ = 91.150 (2)°	0.09 × 0.04 × 0.02 mm
V = 1275.23 (13) Å^3

Data collection

Bruker SMART APEX2 CCD diffractometer	7348 independent reflections
Radiation source: Daresbury SRS station 9.8, Cernik et al., 1997, Clegg, 2003	6485 reflections with I > 2σ(I)
Silicon 111 monochromator	Rint = 0.020
fine–slice ω scans	θmax = 28.7°, θmin = 2.5°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −7→7
Tmin = 0.805, Tmax = 0.951	k = −21→21
13690 measured reflections	l = −23→23

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0386P)^2 + 0.6363P] where P = (Fo^2 + 2Fc^2)/3
7348 reflections	(Δ/σ)max = 0.002
337 parameters	Δρmax = 0.91 e Å^−3
0 restraints	Δρmin = −1.02 e Å^−3

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

	x	y	z	Uiso*/Ueq
C11	0.2703 (4)	0.36705 (13)	0.72743 (12)	0.0181 (4)
C12	0.1069 (4)	0.41652 (15)	0.67819 (13)	0.0236 (4)
C13	0.1433 (5)	0.41921 (16)	0.59626 (14)	0.0276 (5)
C14	0.3419 (4)	0.37023 (15)	0.56525 (13)	0.0239 (4)
N14	0.3903 (5)	0.37564 (15)	0.47910 (13)	0.0336 (5)
O141	0.2650 (5)	0.42717 (18)	0.44014 (13)	0.0617 (5)
O142	0.5530 (5)	0.32985 (18)	0.44984 (13)	0.0617 (5)
C15	0.5012 (5)	0.31757 (15)	0.61120 (14)	0.0261 (4)
C16	0.4655 (4)	0.31683 (14)	0.69373 (13)	0.0229 (4)
C17	0.2285 (4)	0.37138 (13)	0.81642 (12)	0.0173 (3)
O17	0.0057 (3)	0.37990 (11)	0.83855 (10)	0.0237 (3)
N11	0.4492 (3)	0.36757 (11)	0.86863 (10)	0.0175 (3)
C21	0.4595 (4)	0.37373 (12)	0.95521 (12)	0.0162 (3)
C22	0.2756 (4)	0.41979 (13)	0.99830 (12)	0.0191 (4)
C23	0.2917 (4)	0.42302 (13)	1.08301 (12)	0.0197 (4)
C24	0.4927 (4)	0.38031 (13)	1.12518 (12)	0.0186 (4)
I24	0.49134 (3)	0.377222 (9)	1.251935 (8)	0.02616 (5)
C25	0.6842 (4)	0.33725 (13)	1.08288 (13)	0.0192 (4)
C26	0.6668 (4)	0.33385 (13)	0.99815 (12)	0.0178 (3)
C31	1.1985 (4)	0.13179 (13)	0.28880 (12)	0.0169 (3)
C32	1.3693 (4)	0.08409 (14)	0.33724 (13)	0.0212 (4)
C33	1.3397 (4)	0.08116 (15)	0.41934 (14)	0.0252 (4)
C34	1.1387 (4)	0.12822 (14)	0.45198 (13)	0.0223 (4)
N34	1.0972 (4)	0.12133 (14)	0.53831 (12)	0.0295 (4)
O341	1.2305 (5)	0.07091 (17)	0.57634 (12)	0.0538 (6)
O342	0.9268 (5)	0.16422 (17)	0.56791 (12)	0.0517 (6)
C35	0.9719 (4)	0.17910 (15)	0.40647 (13)	0.0238 (4)
C36	1.0020 (4)	0.18036 (14)	0.32363 (13)	0.0219 (4)
C37	1.2340 (4)	0.12830 (13)	0.19952 (12)	0.0175 (3)
O37	1.4553 (3)	0.12042 (11)	0.17583 (9)	0.0225 (3)
N31	1.0101 (3)	0.13254 (11)	0.14847 (10)	0.0176 (3)
C41	1.0029 (4)	0.12971 (12)	0.06208 (12)	0.0161 (3)
C42	1.1965 (4)	0.17243 (13)	0.02499 (12)	0.0180 (4)
C43	1.1850 (4)	0.16889 (13)	−0.05934 (12)	0.0188 (4)
C44	0.9775 (4)	0.12365 (13)	−0.10744 (12)	0.0179 (4)
I44	0.97313 (3)	0.119495 (9)	−0.235056 (8)	0.02594 (5)
C45	0.7802 (4)	0.08235 (13)	−0.07119 (12)	0.0198 (4)
C46	0.7942 (4)	0.08527 (13)	0.01351 (12)	0.0188 (4)
H12	−0.0304	0.4486	0.7009	0.028*
H13	0.0351	0.4537	0.5624	0.033*
H15	0.6312	0.2829	0.5872	0.031*
H16	0.5741	0.2821	0.7272	0.028*
H11	0.6080	0.3661	0.8491	0.021*
H22	0.1387	0.4491	0.9695	0.023*
H23	0.1658	0.4543	1.1122	0.024*
H25	0.8257	0.3104	1.1120	0.023*
H26	0.7963	0.3043	0.9691	0.021*
H32	1.5075	0.0532	0.3137	0.025*
H33	1.4538	0.0478	0.4526	0.030*
H35	0.8402	0.2123	0.4311	0.029*
H36	0.8888	0.2143	0.2907	0.026*
H31	0.8506	0.1278	0.1669	0.021*
H42	1.3368	0.2041	0.0578	0.022*
H43	1.3186	0.1973	−0.0845	0.023*
H45	0.6371	0.0524	−0.1041	0.024*
H46	0.6605	0.0568	0.0386	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0171 (8)	0.0214 (9)	0.0165 (9)	0.0027 (7)	0.0043 (7)	0.0024 (7)
C12	0.0235 (10)	0.0283 (10)	0.0205 (10)	0.0104 (8)	0.0060 (8)	0.0049 (8)
C13	0.0315 (11)	0.0332 (12)	0.0199 (10)	0.0152 (9)	0.0048 (9)	0.0073 (8)
C14	0.0288 (11)	0.0291 (11)	0.0157 (9)	0.0094 (8)	0.0064 (8)	0.0055 (8)
N14	0.0426 (12)	0.0407 (12)	0.0197 (9)	0.0171 (10)	0.0083 (9)	0.0062 (8)
O141	0.0834 (12)	0.0837 (12)	0.0269 (7)	0.0569 (10)	0.0249 (8)	0.0211 (8)
O142	0.0834 (12)	0.0837 (12)	0.0269 (7)	0.0569 (10)	0.0249 (8)	0.0211 (8)
C15	0.0282 (11)	0.0315 (11)	0.0201 (10)	0.0133 (9)	0.0069 (8)	0.0028 (8)
C16	0.0231 (10)	0.0264 (10)	0.0203 (10)	0.0092 (8)	0.0047 (8)	0.0029 (8)
C17	0.0147 (8)	0.0200 (9)	0.0177 (9)	0.0019 (7)	0.0041 (7)	0.0024 (7)
O17	0.0141 (6)	0.0377 (9)	0.0195 (7)	0.0034 (6)	0.0043 (5)	0.0017 (6)
N11	0.0132 (7)	0.0230 (8)	0.0169 (8)	0.0016 (6)	0.0048 (6)	0.0012 (6)
C21	0.0141 (8)	0.0179 (8)	0.0170 (8)	0.0007 (6)	0.0038 (7)	0.0022 (6)
C22	0.0170 (8)	0.0227 (9)	0.0179 (9)	0.0039 (7)	0.0031 (7)	0.0009 (7)
C23	0.0182 (9)	0.0224 (9)	0.0191 (9)	0.0034 (7)	0.0062 (7)	0.0009 (7)
C24	0.0202 (9)	0.0193 (9)	0.0165 (9)	−0.0014 (7)	0.0032 (7)	0.0013 (7)
I24	0.03405 (9)	0.02879 (8)	0.01610 (7)	0.00239 (6)	0.00462 (5)	0.00208 (5)
C25	0.0156 (8)	0.0210 (9)	0.0213 (9)	0.0012 (7)	0.0028 (7)	0.0021 (7)
C26	0.0139 (8)	0.0207 (9)	0.0195 (9)	0.0027 (6)	0.0038 (7)	0.0029 (7)
C31	0.0153 (8)	0.0215 (9)	0.0145 (8)	0.0026 (7)	0.0028 (7)	0.0022 (7)
C32	0.0188 (9)	0.0266 (10)	0.0195 (9)	0.0078 (7)	0.0034 (7)	0.0052 (7)
C33	0.0250 (10)	0.0328 (11)	0.0196 (10)	0.0114 (8)	0.0039 (8)	0.0078 (8)
C34	0.0248 (10)	0.0275 (10)	0.0156 (9)	0.0044 (8)	0.0056 (8)	0.0028 (7)
N34	0.0365 (11)	0.0372 (11)	0.0171 (8)	0.0124 (9)	0.0090 (8)	0.0064 (7)
O341	0.0720 (15)	0.0742 (15)	0.0228 (9)	0.0454 (13)	0.0180 (9)	0.0223 (10)
O342	0.0624 (14)	0.0757 (15)	0.0234 (9)	0.0443 (12)	0.0199 (9)	0.0130 (9)
C35	0.0247 (10)	0.0281 (11)	0.0194 (10)	0.0084 (8)	0.0058 (8)	0.0010 (8)
C36	0.0205 (9)	0.0274 (10)	0.0180 (9)	0.0092 (8)	0.0030 (7)	0.0015 (7)
C37	0.0169 (8)	0.0198 (9)	0.0159 (8)	0.0025 (7)	0.0013 (7)	0.0020 (7)
O37	0.0142 (6)	0.0349 (8)	0.0190 (7)	0.0031 (6)	0.0040 (5)	0.0026 (6)
N31	0.0126 (7)	0.0262 (8)	0.0143 (7)	0.0016 (6)	0.0029 (6)	0.0018 (6)
C41	0.0166 (8)	0.0183 (8)	0.0139 (8)	0.0038 (6)	0.0031 (7)	0.0021 (6)
C42	0.0157 (8)	0.0198 (9)	0.0186 (9)	−0.0010 (7)	0.0012 (7)	0.0028 (7)
C43	0.0190 (9)	0.0195 (9)	0.0188 (9)	0.0015 (7)	0.0050 (7)	0.0032 (7)
C44	0.0207 (9)	0.0183 (9)	0.0151 (8)	0.0056 (7)	0.0026 (7)	0.0017 (6)
I44	0.03629 (9)	0.02770 (8)	0.01409 (7)	−0.00052 (6)	0.00410 (5)	0.00192 (5)
C45	0.0174 (8)	0.0233 (9)	0.0186 (9)	0.0009 (7)	0.0022 (7)	0.0014 (7)
C46	0.0170 (8)	0.0225 (9)	0.0171 (9)	0.0000 (7)	0.0034 (7)	0.0016 (7)

Geometric parameters (Å, º)

C11—C12	1.392 (3)	C31—C32	1.390 (3)
C11—C16	1.396 (3)	C31—C36	1.396 (3)
C11—C17	1.498 (3)	C31—C37	1.496 (3)
C12—C13	1.385 (3)	C32—C33	1.380 (3)
C12—H12	0.95	C32—H32	0.95
C13—C14	1.381 (3)	C33—C34	1.387 (3)
C13—H13	0.95	C33—H33	0.95
C14—C15	1.381 (3)	C34—C35	1.381 (3)
C14—N14	1.474 (3)	C34—N34	1.471 (3)
N14—O142	1.204 (3)	N34—O342	1.212 (3)
N14—O141	1.216 (3)	N34—O341	1.217 (3)
C15—C16	1.391 (3)	C35—C36	1.390 (3)
C15—H15	0.95	C35—H35	0.95
C16—H16	0.95	C36—H36	0.95
C17—O17	1.233 (2)	C37—O37	1.235 (2)
C17—N11	1.356 (2)	C37—N31	1.359 (2)
N11—C21	1.417 (2)	N31—C41	1.417 (2)
N11—H11	0.90	N31—H31	0.90
C21—C22	1.394 (3)	C41—C42	1.394 (3)
C21—C26	1.398 (3)	C41—C46	1.394 (3)
C22—C23	1.387 (3)	C42—C43	1.381 (3)
C22—H22	0.95	C42—H42	0.95
C23—C24	1.392 (3)	C43—C44	1.391 (3)
C23—H23	0.95	C43—H43	0.95
C24—C25	1.395 (3)	C44—C45	1.390 (3)
C24—I24	2.095 (2)	C44—I44	2.096 (2)
C25—C26	1.387 (3)	C45—C46	1.387 (3)
C25—H25	0.95	C45—H45	0.95
C26—H26	0.95	C46—H46	0.95
C12—C11—C16	120.15 (19)	C32—C31—C36	120.14 (19)
C12—C11—C17	117.27 (18)	C32—C31—C37	117.55 (17)
C16—C11—C17	122.57 (18)	C36—C31—C37	122.31 (18)
C13—C12—C11	120.37 (19)	C33—C32—C31	120.50 (19)
C13—C12—H12	119.8	C33—C32—H32	119.8
C11—C12—H12	119.8	C31—C32—H32	119.8
C14—C13—C12	118.0 (2)	C32—C33—C34	118.18 (19)
C14—C13—H13	121.0	C32—C33—H33	120.9
C12—C13—H13	121.0	C34—C33—H33	120.9
C15—C14—C13	123.4 (2)	C35—C34—C33	122.9 (2)
C15—C14—N14	118.08 (19)	C35—C34—N34	118.74 (19)
C13—C14—N14	118.48 (19)	C33—C34—N34	118.33 (19)
O142—N14—O141	122.2 (2)	O342—N34—O341	122.7 (2)
O142—N14—C14	119.3 (2)	O342—N34—C34	118.70 (19)
O141—N14—C14	118.4 (2)	O341—N34—C34	118.53 (19)
C14—C15—C16	117.89 (19)	C34—C35—C36	118.16 (19)
C14—C15—H15	121.1	C34—C35—H35	120.9
C16—C15—H15	121.1	C36—C35—H35	120.9
C15—C16—C11	120.10 (19)	C35—C36—C31	120.03 (19)
C15—C16—H16	119.9	C35—C36—H36	120.0
C11—C16—H16	119.9	C31—C36—H36	120.0
O17—C17—N11	123.95 (19)	O37—C37—N31	123.80 (18)
O17—C17—C11	120.44 (18)	O37—C37—C31	120.40 (18)
N11—C17—C11	115.59 (17)	N31—C37—C31	115.78 (17)
C17—N11—C21	125.68 (16)	C37—N31—C41	124.21 (16)
C17—N11—H11	119.9	C37—N31—H31	121.0
C21—N11—H11	114.2	C41—N31—H31	114.0
C22—C21—C26	119.56 (18)	C42—C41—C46	119.51 (18)
C22—C21—N11	122.32 (17)	C42—C41—N31	121.22 (18)
C26—C21—N11	118.10 (17)	C46—C41—N31	119.25 (17)
C23—C22—C21	120.24 (18)	C43—C42—C41	120.18 (18)
C23—C22—H22	119.9	C43—C42—H42	119.9
C21—C22—H22	119.9	C41—C42—H42	119.9
C22—C23—C24	119.89 (18)	C42—C43—C44	119.97 (19)
C22—C23—H23	120.1	C42—C43—H43	120.0
C24—C23—H23	120.1	C44—C43—H43	120.0
C23—C24—C25	120.26 (19)	C45—C44—C43	120.42 (19)
C23—C24—I24	118.76 (15)	C45—C44—I44	121.40 (15)
C25—C24—I24	120.92 (15)	C43—C44—I44	118.19 (15)
C26—C25—C24	119.64 (18)	C46—C45—C44	119.40 (19)
C26—C25—H25	120.2	C46—C45—H45	120.3
C24—C25—H25	120.2	C44—C45—H45	120.3
C25—C26—C21	120.31 (18)	C45—C46—C41	120.50 (19)
C25—C26—H26	119.8	C45—C46—H46	119.8
C21—C26—H26	119.8	C41—C46—H46	119.8
C16—C11—C12—C13	−2.6 (3)	C36—C31—C32—C33	2.8 (3)
C17—C11—C12—C13	176.7 (2)	C37—C31—C32—C33	−177.0 (2)
C11—C12—C13—C14	1.2 (4)	C31—C32—C33—C34	−1.1 (3)
C12—C13—C14—C15	1.4 (4)	C32—C33—C34—C35	−1.5 (4)
C12—C13—C14—N14	−177.3 (2)	C32—C33—C34—N34	176.6 (2)
C15—C14—N14—O142	5.1 (4)	C35—C34—N34—O342	−3.9 (4)
C13—C14—N14—O142	−176.1 (3)	C33—C34—N34—O342	177.9 (3)
C15—C14—N14—O141	−174.2 (3)	C35—C34—N34—O341	174.1 (3)
C13—C14—N14—O141	4.6 (4)	C33—C34—N34—O341	−4.1 (4)
C13—C14—C15—C16	−2.6 (4)	C33—C34—C35—C36	2.4 (4)
N14—C14—C15—C16	176.1 (2)	N34—C34—C35—C36	−175.8 (2)
C14—C15—C16—C11	1.1 (4)	C34—C35—C36—C31	−0.7 (3)
C12—C11—C16—C15	1.4 (3)	C32—C31—C36—C35	−1.8 (3)
C17—C11—C16—C15	−177.8 (2)	C37—C31—C36—C35	177.9 (2)
C12—C11—C17—O17	33.7 (3)	C32—C31—C37—O37	−32.2 (3)
C16—C11—C17—O17	−147.0 (2)	C36—C31—C37—O37	148.1 (2)
C12—C11—C17—N11	−144.7 (2)	C32—C31—C37—N31	146.52 (19)
C16—C11—C17—N11	34.6 (3)	C36—C31—C37—N31	−33.2 (3)
O17—C17—N11—C21	−0.8 (3)	O37—C37—N31—C41	−0.9 (3)
C11—C17—N11—C21	177.53 (18)	C31—C37—N31—C41	−179.62 (18)
C17—N11—C21—C22	−27.9 (3)	C37—N31—C41—C42	−38.8 (3)
C17—N11—C21—C26	153.85 (19)	C37—N31—C41—C46	142.9 (2)
C26—C21—C22—C23	−2.6 (3)	C46—C41—C42—C43	−1.6 (3)
N11—C21—C22—C23	179.15 (19)	N31—C41—C42—C43	−179.87 (17)
C21—C22—C23—C24	0.2 (3)	C41—C42—C43—C44	0.9 (3)
C22—C23—C24—C25	2.6 (3)	C42—C43—C44—C45	0.4 (3)
C22—C23—C24—I24	−174.65 (15)	C42—C43—C44—I44	−179.36 (14)
C23—C24—C25—C26	−2.9 (3)	C43—C44—C45—C46	−1.1 (3)
I24—C24—C25—C26	174.33 (15)	I44—C44—C45—C46	178.65 (15)
C24—C25—C26—C21	0.4 (3)	C44—C45—C46—C41	0.5 (3)
C22—C21—C26—C25	2.4 (3)	C42—C41—C46—C45	0.9 (3)
N11—C21—C26—C25	−179.33 (18)	N31—C41—C46—C45	179.20 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O17^i	0.90	2.06	2.935 (2)	163
N31—H31···O37^ii	0.90	2.04	2.915 (2)	164
C13—H13···O141^iii	0.95	2.41	3.233 (4)	145
C15—H15···O342	0.95	2.40	3.305 (4)	159
C33—H33···O341^iv	0.95	2.50	3.231 (3)	134
C35—H35···O142	0.95	2.36	3.254 (3)	157

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x, −y+1, −z+1; (iv) −x+3, −y, −z+1.

 

Footnotes

¹Supplementary data for this paper are available from the IUCr electronic archives (Reference: BM5035 ). Services for accessing these data are described at the back of the journal.