4-Nitro­phenyl 2-iodo­benzoate: sheets built from C—H⋯O hydrogen bonds and two-centre iodo–nitro inter­actions

Wardell, J.L.; Skakle, J.M.S.; Low, J.N.; Glidewell, C.

doi:10.1107/S1600536805029272

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 10| October 2005| Pages o3334-o3336

doi:10.1107/S1600536805029272

4-Nitrophenyl 2-iodobenzoate: sheets built from C—H⋯O hydrogen bonds and two-centre iodo–nitro interactions

James L. Wardell,^a Janet M. S. Skakle,^b John N. Low ^b and Christopher Glidewell ^c ^*

^aInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, CP 68563, 21945-970 Rio de Janeiro, RJ, Brazil, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 14 September 2005; accepted 15 September 2005; online 21 September 2005)

Molecules of the title compound, C₁₃H₈INO₄, are linked into complex sheets by two C—H⋯O hydrogen bonds and one two-centre iodo–nitro interaction.

Comment

We have recently reported the molecular and supramolecular structures of a wide range of iodoaryl–nitroaryl compounds, including sulfonamides (Kelly et al., 2002 ), benzylideneanilines (Glidewell, Howie et al., 2002 ; Wardell et al., 2002 ), benzylanilines (Glidewell, Low et al., 2002 ; Glidewell, Low, Skakle, Wardell & Wardell, 2004 ; Ferguson et al., 2005 ), phenylhydrazones (Glidewell, Low, Skakle & Wardell, 2004 ; Glidewell et al., 2003 ), 1,4-diaryl-2,3-diaza-1,3-butadienes (Glidewell, Low, Skakle & Wardell, 2005 ), N-(iodophenyl)nitrophthalimides (Glidewell, Low, Skakle, Wardell & Wardell, 2005 ) and benzoylhydrazones (Glidewell, Low & Wardell, 2005 ). We have now extended this investigation to include the title ester, 4-nitrophenyl 2-iodobenzoate, (I).

Within the molecule of (I) (Fig. 1), the central ester fragment between atoms C11 and C21 is effectively planar, but the iodinated and nitrated aryl rings make dihedral angles with this plane of 39.9 (2) and 42.7 (2)°, respectively, probably in order to minimize the repulsive intramolecular contacts involving the polarized atom O17. The nitro group makes a dihedral angle of 7.4 (2)° with the adjacent aryl ring. The bond distances and inter-bond angles show no unusual values.

The molecules are linked into complex sheets, the formation of which is readily analysed in terms of two one-dimensional substructures. In the simpler of the two substructures, atom C14 in the iodinated ring of the molecule at (x, y, z) acts as hydrogen-bond donor to carbonyl atom O17 in the molecule at ( $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z), thereby forming a C(7) (Bernstein et al., 1995 ) chain running parallel to the [10 $[\overline{1}]$ ] direction and generated by the n-glide plane at y = 0.75 (Fig. 2).

The second substructure is built from a combination of a C—H⋯O hydrogen bond and an iodo–nitro interaction. Atom C26 in the nitrated ring of the molecule at (x, y, z) acts as hydrogen-bond donor to nitro atom O42 in the molecule at ( $[{1\over 2}]$ − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z), so forming a C(6) chain running parallel to the [010] direction and generated by the 2₁ screw axis along ( $[{1\over 4}]$ , y, $[{3\over 4}]$ ) (Fig. 3). In addition, atom I12 in the molecule at (x, y, z) forms a short contact with atom O41 in the molecule at (x, 1 + y, z), with I⋯Oⁱ = 3.240 (2) Å and C—I⋯Oⁱ = 169.8 (2)° [symmetry code: (i) x, 1 + y, z], thus generating by translation a C(11) (Starbuck et al., 1999 ) chain, also running parallel to the [010] direction. The combination of these two interactions then generates a [010] chain of edge-fused R₃³(17) rings (Fig. 3).

The combination of the [010] and [10 $[\overline{1}]$ ] chains generates a (101) sheet in the form of a (4,4)-net. If just the C—H⋯O hydrogen bonds are considered, this sheet is built from two types of R₄⁴(38) ring (Fig. 4).

Figure 1
The molecule of compound (I)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
Part of the crystal structure of (I)

, showing the formation of a C(7) chain along [10 $[\overline{1}]$ ]. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions ( $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z) and (− $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z), respectively.

Figure 3
Part of the crystal structure of (I)

, showing the formation of a chain of edge-fused R₃³(17) rings along [010]. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*), a hash (#) or an ampersand (&) are at the symmetry positions ( $[{1\over 2}]$ − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z), (x, 1 + y, z) and ( $[{1\over 2}]$ − x, − $[{1\over 2}]$ + y, $[{3\over 2}]$ − z), respectively.

Figure 4
Stereoview of part of the crystal structure of compound (I)

, showing the formation of a hydrogen-bonded (101) sheet of R₄⁴(38) rings. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

Experimental

A solution containing equimolar quantities (2 mmol of each) of 4-nitrophenol and 2-iodobenzoyl chloride in chloroform (50 ml) was heated under reflux for 1 h; the solvent was removed under reduced pressure and the resulting solid residue was recrystallized from ethanol to yield crystals suitable for single-crystal X-ray diffraction.

Crystal data

C₁₃H₈INO₄
M_r = 369.10
Monoclinic, P 2₁ /n
a = 9.7231 (4) Å
b = 11.7890 (3) Å
c = 11.1187 (4) Å
β = 97.363 (2)°
V = 1263.98 (8) Å³
Z = 4
D_x = 1.940 Mg m⁻³
Mo Kα radiation
Cell parameters from 2905 reflections
θ = 3.0–27.5°
μ = 2.54 mm⁻¹
T = 120 (2) K
Plate, colourless
0.10 × 0.08 × 0.01 mm

Data collection

Bruker Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003 )T_min = 0.814, T_max = 0.975
12630 measured reflections
2905 independent reflections
2570 reflections with I > 2σ(I)
R_int = 0.036
θ_max = 27.5°
h = −12 → 11
k = −13 → 15
l = −14 → 14

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.058
S = 1.10
2905 reflections
172 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0125P)² + 1.8703P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O17ⁱ	0.95	2.50	3.334 (3)	147
C26—H26⋯O42ⁱⁱ	0.95	2.54	3.395 (3)	149
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

All H atoms were located in difference maps and then treated as riding atoms, with C—H distances of 0.95 Å and U_iso(H) = 1.2U_eq(C).

Data collection: COLLECT (Hooft, 1999 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536805029272/lh6502sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536805029272/lh6502Isup2.hkl

Comment top

We have recently reported the molecular and supramolecular structures of a wide range of iodoaryl–nitroaryl compounds, including sulfonamides (Kelly et al., 2002), benzylideneanilines (Glidewell, Howie et al., 2002; Wardell et al., 2002), benzylanilines (Glidewell, Low et al., 2002; Glidewell, Low, Skakle, Wardell & Wardell, 2004; Ferguson et al., 2005), phenylhydrazones (Glidewell, Low, Skakle & Wardell, 2004; Glidewell et al., 2003), 1,4-diaryl-2,3-diaza-1,3-butadienes (Glidewell, Low, Skakle & Wardell, 2005), N-(iodophenyl)nitrophthalimides (Glidewell, Low, Skakle, Wardell & Wardell, 2005) and benzoylhydrazones (Glidewell, Low & Wardell, 2005). We have now extended this investigation to include the title ester 4-nitrophenyl 2-iodobenzoate, (I).

Within the molecule of (I) (Fig. 1), the central ester fragment between atoms C11 and C21 is effectively planar, but the iodinated and nitrated aryl rings make dihedral angles with this plane of 39.9 (2) and 42.7 (2)°, respectively, probably in order to minimize the repulsive intramolecular contacts involving the polarized atom O17: the nitro group makes a dihedral angle of 7.4 (2)° with the adjacent aryl ring. The bond distances and inter-bond angles show no unusual values.

The molecules are linked into complex sheets, whose formation is readily analysed in terms of two one-dimensional substructures. In the simpler of the two substructures, atom C14 in the iodinated ring of the molecule at (x, y, z) acts as hydrogen-bond donor to carbonyl atom O17 in the molecule at (1/2 + x, 1.5 − y, −1/2 + z), thereby forming a C(7) (Bernstein et al., 1995) chain running parallel to the [101] direction and generated by the n-glide plane at y = 0.75 (Fig. 2).

The second substructure is built from a combination of a C—H···O hydrogen bond and an iodo–nitro interaction. Atom C26 in the nitrated ring of the molecule at (x, y, z) acts as hydrogen-bond donor to nitro atom O42 in the molecule at (1/2 − x, 1/2 + y, 1.5 − z), so forming a C(6) chain running parallel to the [010] direction and generated by the 2₁ screw axis along (1/4, y, 3/4) (Fig. 3). In addition, atom I12 in the molecule at (x, y, z) forms a short contact with atom O41 in the molecule at (x, 1 + y, z), with I···Oⁱ = 3.240 (2) Å and C—I···Oⁱ = 169.8 (2)° [symmetry code: (i) x, 1 + y, z)], thus generating by translation a C(11) (Starbuck et al., 1999) chain, also running parallel to the [010] direction. The combination of these two interactions then generates a [010] chain of edge-fused R₃³(17) rings (Fig. 3)

The combination of the [010] and [101] chains generates a (101) sheet in the form of a (4,4)-net: if just the C—H···O hydrogen bonds are considered, this sheet is built from two types of R₄⁴(38) ring (Fig. 4).

Experimental top

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. The molecule of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I), showing the formation of a C(7) chain along [101]. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (1/2 + x, 1.5 − y, −1/2 + z) and (−1/2 + x, 1.5 − y, 1/2 + z), respectively.
	Fig. 3. Part of the crystal structure of (I), showing the formation of a chain of edge-fused R₃³(17) rings along [010]. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*), a hash (#) or an ampersand (&) are at the symmetry positions (1/2 − x, 1/2 + y, 1.5 − z), (x, 1 + y, z) and (1/2 − x, −1/2 + y, 1.5 − z), respectively.
	Fig. 4. Stereoview of part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded (101) sheet of R₄⁴(38) rings. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

4-Nitrophenyl 2-iodobenzoate top

Crystal data top

C₁₃H₈INO₄	F(000) = 712
M_r = 369.10	D_x = 1.940 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2905 reflections
a = 9.7231 (4) Å	θ = 3.0–27.5°
b = 11.7890 (3) Å	µ = 2.54 mm⁻¹
c = 11.1187 (4) Å	T = 120 K
β = 97.363 (2)°	Plate, colourless
V = 1263.98 (8) Å³	0.10 × 0.08 × 0.01 mm
Z = 4

Data collection top

Bruker–Nonius 95mm CCD camera on κ goniostat diffractometer	2905 independent reflections
Radiation source: Bruker-Nonius FR91 rotating anode	2570 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans	h = −12→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −13→15
T_min = 0.814, T_max = 0.975	l = −14→14
12630 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0125P)² + 1.8703P] where P = (F_o² + 2F_c²)/3
2905 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.80 e Å⁻³
0 restraints	Δρ_min = −0.91 e Å⁻³

Crystal data top

C₁₃H₈INO₄	V = 1263.98 (8) Å³
M_r = 369.10	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7231 (4) Å	µ = 2.54 mm⁻¹
b = 11.7890 (3) Å	T = 120 K
c = 11.1187 (4) Å	0.10 × 0.08 × 0.01 mm
β = 97.363 (2)°

Data collection top

Bruker–Nonius 95mm CCD camera on κ goniostat diffractometer	2905 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2570 reflections with I > 2σ(I)
T_min = 0.814, T_max = 0.975	R_int = 0.036
12630 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 1.10	Δρ_max = 0.80 e Å⁻³
2905 reflections	Δρ_min = −0.91 e Å⁻³
172 parameters

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

	x	y	z	U_iso*/U_eq
I12	0.580705 (19)	0.888948 (14)	0.650830 (16)	0.02111 (7)
O1	0.62987 (19)	0.51101 (15)	0.59123 (16)	0.0181 (4)
O17	0.6392 (2)	0.63226 (16)	0.75041 (17)	0.0223 (4)
O41	0.3784 (2)	0.06357 (16)	0.7691 (2)	0.0298 (5)
O42	0.2579 (2)	0.18618 (17)	0.8565 (2)	0.0301 (5)
N24	0.3467 (2)	0.1619 (2)	0.7914 (2)	0.0217 (5)
C11	0.7462 (3)	0.6829 (2)	0.5758 (2)	0.0160 (5)
C12	0.7347 (3)	0.8009 (2)	0.5729 (2)	0.0177 (5)
C13	0.8224 (3)	0.8659 (2)	0.5107 (3)	0.0238 (6)
C14	0.9227 (3)	0.8134 (3)	0.4527 (3)	0.0279 (7)
C15	0.9341 (3)	0.6962 (3)	0.4530 (3)	0.0272 (7)
C16	0.8463 (3)	0.6312 (2)	0.5131 (2)	0.0204 (6)
C17	0.6661 (3)	0.6105 (2)	0.6508 (2)	0.0166 (5)
C21	0.5571 (3)	0.4276 (2)	0.6460 (2)	0.0164 (5)
C22	0.5994 (3)	0.3177 (2)	0.6297 (2)	0.0170 (5)
C23	0.5297 (3)	0.2288 (2)	0.6755 (2)	0.0175 (5)
C24	0.4191 (3)	0.2544 (2)	0.7381 (2)	0.0171 (5)
C25	0.3732 (3)	0.3646 (2)	0.7521 (2)	0.0190 (5)
C26	0.4434 (3)	0.4527 (2)	0.7041 (2)	0.0184 (5)
H13	0.8132	0.9461	0.5082	0.029*
H14	0.9842	0.8579	0.4124	0.033*
H15	1.0022	0.6605	0.4118	0.033*
H16	0.8536	0.5509	0.5121	0.024*
H22	0.6762	0.3032	0.5871	0.020*
H23	0.5567	0.1524	0.6645	0.021*
H25	0.2955	0.3793	0.7936	0.023*
H26	0.4139	0.5290	0.7110	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I12	0.02273 (11)	0.01574 (11)	0.02471 (11)	0.00248 (7)	0.00243 (8)	0.00048 (7)
O1	0.0217 (10)	0.0145 (9)	0.0183 (9)	−0.0039 (7)	0.0034 (8)	0.0002 (7)
O17	0.0277 (11)	0.0198 (9)	0.0207 (10)	−0.0062 (8)	0.0080 (8)	−0.0028 (8)
O41	0.0316 (12)	0.0136 (9)	0.0453 (13)	−0.0025 (9)	0.0091 (10)	0.0033 (9)
O42	0.0277 (12)	0.0280 (11)	0.0372 (12)	−0.0072 (9)	0.0150 (10)	−0.0014 (9)
N24	0.0205 (12)	0.0184 (11)	0.0254 (12)	−0.0037 (10)	0.0003 (10)	0.0022 (10)
C11	0.0170 (13)	0.0167 (12)	0.0141 (12)	−0.0013 (10)	0.0012 (10)	−0.0036 (10)
C12	0.0173 (13)	0.0195 (13)	0.0161 (12)	−0.0001 (10)	0.0011 (10)	−0.0009 (10)
C13	0.0271 (16)	0.0237 (14)	0.0197 (13)	−0.0088 (12)	−0.0004 (12)	0.0048 (11)
C14	0.0211 (15)	0.0426 (18)	0.0200 (14)	−0.0115 (13)	0.0031 (12)	0.0047 (13)
C15	0.0207 (15)	0.0418 (18)	0.0200 (14)	−0.0022 (13)	0.0058 (11)	−0.0070 (13)
C16	0.0180 (14)	0.0257 (14)	0.0176 (13)	−0.0040 (11)	0.0028 (11)	−0.0022 (11)
C17	0.0172 (13)	0.0122 (12)	0.0199 (13)	0.0008 (10)	−0.0002 (11)	0.0015 (10)
C21	0.0182 (13)	0.0133 (12)	0.0164 (12)	−0.0048 (10)	−0.0021 (10)	0.0017 (10)
C22	0.0178 (13)	0.0142 (12)	0.0180 (12)	−0.0016 (10)	−0.0014 (10)	0.0017 (10)
C23	0.0178 (13)	0.0141 (12)	0.0197 (13)	0.0017 (10)	−0.0009 (11)	−0.0008 (10)
C24	0.0165 (13)	0.0147 (12)	0.0193 (13)	−0.0047 (10)	−0.0008 (10)	0.0033 (10)
C25	0.0165 (13)	0.0191 (13)	0.0217 (13)	0.0013 (11)	0.0031 (11)	−0.0022 (10)
C26	0.0164 (13)	0.0149 (12)	0.0234 (13)	0.0023 (10)	0.0012 (11)	0.0000 (10)

Geometric parameters (Å, º) top

C11—C12	1.396 (4)	C17—O17	1.198 (3)
C11—C16	1.406 (4)	C21—C22	1.378 (4)
C11—C17	1.482 (4)	C21—C26	1.382 (4)
C12—C13	1.394 (4)	C22—C23	1.381 (4)
C12—I12	2.098 (3)	C22—H22	0.95
C13—C14	1.383 (4)	C23—C24	1.387 (4)
C13—H13	0.95	C23—H23	0.95
C14—C15	1.386 (4)	C24—C25	1.389 (4)
C14—H14	0.95	C24—N24	1.463 (3)
C15—C16	1.381 (4)	N24—O42	1.229 (3)
C15—H15	0.95	N24—O41	1.233 (3)
C16—H16	0.95	C25—C26	1.388 (4)
O1—C17	1.371 (3)	C25—H25	0.95
O1—C21	1.396 (3)	C26—H26	0.95

C12—C11—C16	118.6 (2)	C22—C21—C26	122.2 (2)
C12—C11—C17	122.7 (2)	C22—C21—O1	115.4 (2)
C16—C11—C17	118.5 (2)	C26—C21—O1	122.2 (2)
C13—C12—C11	120.5 (3)	C21—C22—C23	119.8 (3)
C13—C12—I12	116.6 (2)	C21—C22—H22	120.1
C11—C12—I12	122.87 (19)	C23—C22—H22	120.1
C14—C13—C12	119.8 (3)	C22—C23—C24	117.9 (2)
C14—C13—H13	120.1	C22—C23—H23	121.0
C12—C13—H13	120.1	C24—C23—H23	121.0
C13—C14—C15	120.4 (3)	C23—C24—C25	122.7 (2)
C13—C14—H14	119.8	C23—C24—N24	119.0 (2)
C15—C14—H14	119.8	C25—C24—N24	118.3 (2)
C16—C15—C14	119.9 (3)	O42—N24—O41	123.4 (2)
C16—C15—H15	120.0	O42—N24—C24	118.4 (2)
C14—C15—H15	120.0	O41—N24—C24	118.3 (2)
C15—C16—C11	120.6 (3)	C26—C25—C24	118.4 (3)
C15—C16—H16	119.7	C26—C25—H25	120.8
C11—C16—H16	119.7	C24—C25—H25	120.8
C17—O1—C21	120.4 (2)	C21—C26—C25	118.8 (2)
O17—C17—O1	123.8 (2)	C21—C26—H26	120.6
O17—C17—C11	126.2 (2)	C25—C26—H26	120.6
O1—C17—C11	110.0 (2)

C16—C11—C12—C13	−1.1 (4)	C17—O1—C21—C22	−139.1 (2)
C17—C11—C12—C13	173.4 (2)	C17—O1—C21—C26	45.9 (3)
C16—C11—C12—I12	175.25 (19)	C26—C21—C22—C23	−2.0 (4)
C17—C11—C12—I12	−10.2 (4)	O1—C21—C22—C23	−177.0 (2)
C11—C12—C13—C14	−0.8 (4)	C21—C22—C23—C24	−0.7 (4)
I12—C12—C13—C14	−177.3 (2)	C22—C23—C24—C25	2.5 (4)
C12—C13—C14—C15	1.9 (4)	C22—C23—C24—N24	−177.8 (2)
C13—C14—C15—C16	−1.0 (4)	C23—C24—N24—O42	173.0 (2)
C14—C15—C16—C11	−0.9 (4)	C25—C24—N24—O42	−7.3 (4)
C12—C11—C16—C15	1.9 (4)	C23—C24—N24—O41	−6.6 (4)
C17—C11—C16—C15	−172.8 (3)	C25—C24—N24—O41	173.0 (2)
C21—O1—C17—O17	0.1 (4)	C23—C24—C25—C26	−1.7 (4)
C21—O1—C17—C11	178.1 (2)	N24—C24—C25—C26	178.6 (2)
C12—C11—C17—O17	−37.8 (4)	C22—C21—C26—C25	2.8 (4)
C16—C11—C17—O17	136.7 (3)	O1—C21—C26—C25	177.5 (2)
C12—C11—C17—O1	144.3 (2)	C24—C25—C26—C21	−0.9 (4)
C16—C11—C17—O1	−41.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O17ⁱ	0.95	2.50	3.334 (3)	147
C26—H26···O42ⁱⁱ	0.95	2.54	3.395 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₁₃H₈INO₄
M_r	369.10
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	9.7231 (4), 11.7890 (3), 11.1187 (4)
β (°)	97.363 (2)
V (Å³)	1263.98 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.54
Crystal size (mm)	0.10 × 0.08 × 0.01

Data collection
Diffractometer	Bruker–Nonius 95mm CCD camera on κ goniostat diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.814, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	12630, 2905, 2570
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.058, 1.10
No. of reflections	2905
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.91

Computer programs: COLLECT (Hooft, 1999), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O17ⁱ	0.95	2.50	3.334 (3)	147
C26—H26···O42ⁱⁱ	0.95	2.54	3.395 (3)	149

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

Acknowledgements

X-ray data were collected at the EPSRC X-Ray Crystallographic Service, University of Southampton, England; the authors thank the staff of the Service for all their help and advice. JLW thanks CNPq and FAPERJ for financial support.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada. Google Scholar
Ferguson, G., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o445–o449. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Glidewell, C., Howie, R. A., Low, J. N., Skakle, J. M. S., Wardell, J. L. & Wardell, S M. S. V. (2002). Acta Cryst. B58, 864–876. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o98–o101. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2004). Acta Cryst. C60, o19–o23. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o312–o316. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Glidewell, C., Low, J. N., Skakle, J. M. S., Wardell, S. M. S. V. & Wardell, J. L. (2002). Acta Cryst. C58, o487–o490. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Glidewell, C., Low, J. N., Skakle, J. M. S., Wardell, S. M. S. V. & Wardell, J. L. (2004). Acta Cryst. B60, 472–480. Web of Science CSD CrossRef IUCr Journals Google Scholar
Glidewell, C., Low, J. N., Skakle, J. M. S., Wardell, S. M. S. V. & Wardell, J. L. (2005). Acta Cryst. B61, 227–237. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Glidewell, C., Low, J. N. &. Wardell, J. L. (2005). Acta Cryst. E61, o2438–o2440. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Kelly, C. J., Skakle, J. M. S. Wardell, J L., Wardell, S. M. S. V., Low, J. N. & Glidewell, C. (2002). Acta Cryst. B58, 94–108. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELX97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Starbuck, J., Norman, N. C. & Orpen, A. G. (1999). New J. Chem. 23, 969–972. Web of Science CrossRef Google Scholar
Wardell, J. L., Wardell, S. M. S. V., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2002). Acta Cryst. C58, o428–o430. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 10| October 2005| Pages o3334-o3336

doi:10.1107/S1600536805029272

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Nitro­phenyl 2-iodo­benzoate: sheets built from C—H⋯O hydrogen bonds and two-centre iodo–nitro inter­actions

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Nitrophenyl 2-iodobenzoate: sheets built from C—H⋯O hydrogen bonds and two-centre iodo–nitro interactions