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

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ISSN: 2056-9890

2-Nitro­benzaldehyde 2-iodo­benzoyl­hydrazone

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

(Received 1 July 2005; accepted 5 July 2005; online 9 July 2005)

Mol­ecules of the title compound, C14H10IN3O3, are linked into sheets by a combination of N—H⋯O and C—H⋯O hydrogen bonds.

Comment

The title compound, (I)[link], was prepared as part of our study of the supramolecular arrangements of imine and amido compounds.

[Scheme 1]

In the mol­ecules of (I)[link] (Fig. 1[link]), the bond distances (Table 1[link]) in the acyclic acyl­hydrazone fragment C11–C21 are all standard (Allen et al., 1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]), and there is no evidence for any bond fixation within the ar­yl rings. Hence, the conventional representation (I)[link] is entirely appropriate. This central spacer unit is nearly planar, as shown by the key torsional angles, with a trans planar H—N—C=O fragment, as expected, and an E configuration at the C1=N1 bond. However, the ar­yl rings are both twisted out of this plane, making dihedral angles of 38.9 (2) and 43.3 (2)°, while the nitro group is twisted out of the plane of the adjacent ar­yl ring by 33.7 (2)°. Within the spacer unit C11–C21, the intra­chain bond angles are all less than 120°.

The mol­ecules of (I)[link] are linked into sheets by one N—H⋯O hydrogen bond and two C—H⋯O hydrogen bonds, one of which utilizes the carbon­yl O atom as acceptor, while the other utilizes a nitro O atom. Hydrazone atom N2 and methine atom C1 in the mol­ecule at (x, y, z) both act as hydrogen-bond donors to carbon­yl atom O2 in the mol­ecule at (x, −1 + y, z), thus generating by translation a C(4)C(6)[R21(6)] chain of rings (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) running parallel to the [010] direction (Fig. 2[link]). It may be noted here that analogous C(4) motifs are rather common in both carboxamides and sulfonamides.

In addition, ar­yl atom C26 in the mol­ecule at (x, y, z) acts as hydrogen-bond donor to nitro atom O22 in the mol­ecule at (1 − x, −y, −[{1\over 2}] + z), thereby forming a C(11) chain, generated by the 21 screw axis along ([{1\over 2}], 0, z) and running parallel to the [001] direction (Fig. 3[link]). The combination of the simple [001] chains and the [010] chains of rings then generates a complex (100) sheet (Fig. 4[link]). This sheet lies in the domain 0.21 < x < 0.79 and a second such sheet, related to the first by the action of the glide planes, lies in the domain 0.71 < x < 1.29. However, there are no direction-specific inter­actions between adjacent sheets: in particular, C—H⋯π(arene) hydrogen bonds, aromatic ππ stacking inter­actions, and iodo–nitro inter­actions are all absent.

[Figure 1]
Figure 1
The mol­ecule of compound (I)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2]
Figure 2
Part of the crystal structure of compound (I)[link], showing the formation of a C(4)C(6)[R21(6)] chain of rings along [010]. For the sake of clarity, the H atoms on the ar­yl rings have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, −1 + y, z) and (x, 1 + y, z), respectively.
[Figure 3]
Figure 3
Part of the crystal structure of compound (I)[link], showing the formation of a C(11) chain along [001]. For the sake of clarity, the 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 − x, −y, −[{1\over 2}] + z), (1 − x, −y, [{1\over 2}] + z) and (x, y, 1 + z), respectively.
[Figure 4]
Figure 4
Stereoview of part of the crystal structure of compound (I)[link], showing the formation of a (100) sheet. For the sake of clarity, the H atoms not involved in the motifs shown have been omitted.

Experimental

The title compound was prepared by reaction of 2-nitro­benzaldehyde hydrazone with 2-iodo­benzo­yl chloride. A solution containg 2 mmol of each reactant in 1,2-dichloro­ethane (20 ml) was heated under reflux for 1 h; the mixture was cooled and the solvent was removed under reduced pressure. The solid residue was crystallized initially from ethanol, and crystals suitable for single-crystal X-ray diffraction were obtained by slow evaporation of a solution in ethanol and 2-propanol [1/1 (v/v), m.p. > 520 K]. IR (KBr disk): 1680 cm−1.

Crystal data
  • C14H10IN3O3

  • Mr = 395.15

  • Orthorhombic, P c a 21

  • a = 21.6122 (8) Å

  • b = 5.0393 (2) Å

  • c = 12.7868 (5) Å

  • V = 1392.62 (9) Å3

  • Z = 4

  • Dx = 1.885 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 2783 reflections

  • θ = 3.7–27.5°

  • μ = 2.31 mm−1

  • T = 120 (2) K

  • Plate, green

  • 0.28 × 0.08 × 0.05 mm

Data collection
  • Bruker–Nonius KappaCCD diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan(SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.])Tmin = 0.564, Tmax = 0.893

  • 12100 measured reflections

  • 2783 independent reflections

  • 2579 reflections with I > 2σ(I)

  • Rint = 0.036

  • θmax = 27.5°

  • h = −27 → 25

  • k = −6 → 6

  • l = −16 → 14

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.054

  • S = 1.05

  • 2783 reflections

  • 190 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0068P)2 + 2.6684P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max = 0.001

  • Δρmax = 0.62 e Å−3

  • Δρmin = −0.64 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1119 Friedel pairs

  • Flack parameter: −0.01 (2)

Table 1
Selected geometric parameters (Å, °)[link]

C11—C1 1.476 (5)
C1—N1 1.286 (5)
N1—N2 1.396 (5)
N2—C2 1.358 (6)
C2—O2 1.233 (5)
C2—C21 1.482 (5)
C22—I22 2.107 (4)
C11—C1—N1 118.3 (3)
C1—N1—N2 113.2 (3)
N1—N2—C2 119.1 (4)
N2—C2—O2 123.5 (4)
O2—C2—C21 122.2 (4)
N2—C2—C21 114.2 (3)
C12—C11—C1—N1 −151.3 (4)
C11—C1—N1—N2 −175.4 (3)
C1—N1—N2—C2 −174.4 (4)
N1—N2—C2—C21 176.2 (3)
N2—C2—C21—C22 138.2 (4)
C11—C12—N12—O11 18.6 (5)

Table 2
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O2i 0.88 1.98 2.820 (5) 159
C1—H1⋯O2i 0.95 2.27 3.082 (5) 142
C26—H26⋯O22ii 0.95 2.39 3.169 (6) 139
Symmetry codes: (i) x, y-1, z; (ii) [-x+1, -y, z-{\script{1\over 2}}].

All H atoms were located in difference maps and subsequently treated as riding atoms, with distances C—H = 0.95 Å and N—H = 0.88 Å, and with Uiso(H) = 1.2Ueq(C,N). The correct orientation of the structure with respect to the polar-axis direction c (Jones, 1986[Jones, P. G. (1986). Acta Cryst. A42, 57.]) was established using the Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]) parameter.

Data collection: COLLECT (Hooft, 1999[Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[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.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information


Comment top

The title compound, (I), was prepared as part of our study of the supramolecular arrangements of imine and amido compounds.

In the molecules of (I) (Fig. 1), the bond distances (Table 1) in the acyclic acylhydrazone fragment C11–C21 are all typical of their types (Allen et al., 1987), and there is no evidence for any bond fixation within the aryl rings. Hence, the conventional representation (I) is entirely appropriate. This central spacer unit is nearly planar, as shown by the key torsional angles, with a trans planar H—N—CO fragment, as expected, and an E configuration at the C1N1 bond. However, the aryl rings are both twisted out of this plane, making dihedral angles of 38.9 (2) and 43.3 (2)°, while the nitro group is twisted out of the plane of the adjacent aryl ring by 33.7 (2)°. Within the spacer unit C11–C21, the intrachain bond angles are all less than 120°.

The molecules of (I) are linked into sheets by one N—H···O hydrogen bond and two C—H···O hydrogen bonds, one of which utilizes the carbonyl O atom as acceptor, while the other utilizes a nitro O atom. Hydrazone atom N2 and methine atom C1 in the molecule at (x, y, z) both act as hydrogen-bond donors to carbonyl atom O2 in the molecule at (x, -1 + y, z), thus generating by translation a C(4) C(6)[R21(6)] chain of rings (Bernstein et al., 1995) running parallel to the [010] direction (Fig. 2). It may be noted here that analogous C(4) motifs are rather common in both carboxamides and sulfonamides.

In addition, aryl atom C26 in the molecule at (x, y, z) acts as hydrogen-bond donor to nitro atom O22 in the molecule at (1 - x, -y, -1/2 + z), thereby forming a C(11) chain, generated by the 21 screw axis along (1/2, 0, z) and running parallel to the [001] direction (Fig. 3). The combination of the simple [001] chains and the [010] chains of rings then generates a complex (100) sheet (Fig. 4). This sheet lies in the domain 0.21 < x < 0.79 and a second such sheet, related to the first by the action of the glide planes, lies in the domain 0.71 < x < 1.29. However, there are no direction-specific interactions between adjacent sheets: in particular, C—H···π(arene) hydrogen bonds, aromatic ππ stacking interactions, and iodo–nitro interactions are all absent.

Experimental top

The title compound was prepared by reaction of 2-nitrobenzaldehyde hydrazone with 2-iodobenzoyl chloride. A solution containg 2 mmol of each reactant in 1,2-dichloroethane (20 ml) was heated under reflux for 1 h; the mixture was cooled and the solvent was removed under reduced pressure. The solid residue was crystallized initially from ethanol, and crystals suitable for single-crystal X-ray diffraction were obtained by slow evaporation of a solution in ethanol and 2-propanol (1/1 (v/v), m.p. > 520 K). IR (KBr disk): 1680 cm-1.

Refinement top

The systematic absences permitted Pca21 and Pcam (= Pbcm) as possible space groups; Pca21 was selected and confirmed by the successful structure analysis. All H atoms were located from difference maps and subsequently treated as riding atoms, with distances C—H = 0.95 Å and N—H = 0.88 Å, and with Uiso(H) = 1.2Ueq(C,N). The correct orientation of the structure with respect to the polar-axis direction z (Jones, 1986) was established using the Flack (1983) parameter.

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
[Figure 1] Fig. 1. The molecule of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of compound (I), showing the formation of a C(4) C(6)[R21(6)] chain of rings along[010]. For the sake of clarity, the H atoms on the aryl rings have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, -1 + y, z) and (x, 1 + y, z), respectively.
[Figure 3] Fig. 3. Part of the crystal structure of compound (I), showing the formation of a C(11) chain along [001]. For the sake of clarity, the 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 - x, -y, -1/2 + z), (1 - x, -y, 1/2 + z) and (x, y, 1 + z), respectively.
[Figure 4] Fig. 4. Stereoview of part of the crystal structure of compound (I), showing the formation of a (100) sheet. For the sake of clarity, the H atoms not involved in the motifs shown have been omitted.
2-Nitrobenzaldehyde 2-iodobenzoylhydrazone top
Crystal data top
C14H10IN3O3F(000) = 768
Mr = 395.15Dx = 1.885 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 2783 reflections
a = 21.6122 (8) Åθ = 3.7–27.5°
b = 5.0393 (2) ŵ = 2.31 mm1
c = 12.7868 (5) ÅT = 120 K
V = 1392.62 (9) Å3Plate, green
Z = 40.28 × 0.08 × 0.05 mm
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
2783 independent reflections
Radiation source: Bruker-Nonius FR91 rotating anode2579 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.7°
ϕ and ω scansh = 2725
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 66
Tmin = 0.564, Tmax = 0.893l = 1614
12100 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.054 w = 1/[σ2(Fo2) + (0.0068P)2 + 2.6684P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2783 reflectionsΔρmax = 0.62 e Å3
190 parametersΔρmin = 0.64 e Å3
1 restraintAbsolute structure: Flack (1983), 1119 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (2)
Crystal data top
C14H10IN3O3V = 1392.62 (9) Å3
Mr = 395.15Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 21.6122 (8) ŵ = 2.31 mm1
b = 5.0393 (2) ÅT = 120 K
c = 12.7868 (5) Å0.28 × 0.08 × 0.05 mm
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
2783 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2579 reflections with I > 2σ(I)
Tmin = 0.564, Tmax = 0.893Rint = 0.036
12100 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.054Δρmax = 0.62 e Å3
S = 1.05Δρmin = 0.64 e Å3
2783 reflectionsAbsolute structure: Flack (1983), 1119 Friedel pairs
190 parametersAbsolute structure parameter: 0.01 (2)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I220.218672 (9)1.14431 (4)0.18746 (3)0.01788 (7)
O20.35439 (14)1.0376 (5)0.2880 (2)0.0213 (7)
O110.51157 (14)0.1203 (6)0.4398 (2)0.0247 (7)
O220.53559 (14)0.1309 (6)0.5706 (3)0.0266 (7)
N10.39015 (15)0.6282 (6)0.4133 (2)0.0130 (7)
N20.36433 (19)0.5915 (8)0.3143 (3)0.0133 (8)
N120.50990 (15)0.0622 (7)0.5329 (3)0.0159 (7)
C10.40790 (17)0.4105 (8)0.4563 (3)0.0130 (8)
C20.34859 (19)0.8076 (8)0.2566 (3)0.0122 (8)
C110.43163 (19)0.4209 (8)0.5645 (3)0.0113 (8)
C120.47550 (18)0.2408 (8)0.6041 (3)0.0114 (8)
C130.49059 (18)0.2288 (8)0.7098 (3)0.0148 (10)
C140.4634 (2)0.4062 (9)0.7785 (3)0.0186 (9)
C160.4064 (2)0.5965 (12)0.6355 (4)0.0159 (12)
C150.4210 (3)0.5966 (12)0.7408 (4)0.0187 (12)
C210.32548 (19)0.7445 (8)0.1504 (3)0.0107 (8)
C220.27457 (17)0.8738 (7)0.1046 (3)0.0130 (8)
C230.2557 (2)0.8143 (8)0.0036 (3)0.0191 (9)
C240.2873 (2)0.6247 (9)0.0540 (3)0.0218 (9)
C250.3375 (2)0.4930 (8)0.0110 (3)0.0186 (9)
C260.3569 (2)0.5553 (10)0.0908 (4)0.0150 (10)
H10.40580.24710.41940.016*
H20.35830.43050.28960.016*
H130.51920.10030.73450.018*
H140.47330.39990.85080.022*
H160.37740.72380.61070.019*
H150.40290.72250.78680.022*
H230.22110.90330.02600.023*
H240.27440.58490.12330.026*
H250.35870.36130.05030.022*
H260.39190.46760.11960.018*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I220.01464 (11)0.01349 (11)0.02551 (12)0.00233 (9)0.00086 (18)0.0044 (2)
O20.0360 (19)0.0091 (14)0.0188 (15)0.0015 (12)0.0124 (13)0.0027 (12)
O110.0323 (18)0.0245 (17)0.0174 (15)0.0082 (14)0.0042 (13)0.0018 (13)
O220.0232 (17)0.0221 (17)0.0346 (18)0.0128 (13)0.0019 (14)0.0032 (15)
N10.0157 (17)0.0146 (17)0.0088 (15)0.0010 (13)0.0025 (13)0.0002 (13)
N20.019 (2)0.0101 (17)0.0102 (18)0.0024 (15)0.0033 (15)0.0032 (15)
N120.0131 (17)0.0135 (17)0.0209 (19)0.0012 (14)0.0007 (14)0.0057 (14)
C10.0135 (19)0.0125 (19)0.0131 (19)0.0008 (15)0.0029 (15)0.0001 (15)
C20.012 (2)0.011 (2)0.014 (2)0.0020 (16)0.0019 (16)0.0008 (16)
C110.011 (2)0.0107 (19)0.012 (2)0.0043 (16)0.0005 (15)0.0024 (15)
C120.013 (2)0.010 (2)0.011 (2)0.0022 (16)0.0010 (16)0.0021 (17)
C130.0156 (18)0.0139 (18)0.015 (3)0.0013 (15)0.0053 (16)0.0038 (16)
C140.022 (3)0.022 (2)0.012 (2)0.004 (2)0.0054 (18)0.0009 (18)
C160.021 (3)0.011 (2)0.016 (3)0.0017 (19)0.0014 (19)0.0004 (19)
C150.024 (3)0.020 (3)0.012 (3)0.003 (2)0.0011 (19)0.005 (2)
C210.0132 (19)0.0087 (19)0.0101 (19)0.0025 (16)0.0011 (14)0.0027 (14)
C220.0142 (19)0.0102 (19)0.0146 (19)0.0005 (15)0.0004 (15)0.0017 (15)
C230.020 (2)0.019 (2)0.019 (2)0.0017 (17)0.0044 (17)0.0001 (17)
C240.028 (2)0.026 (2)0.012 (2)0.0002 (19)0.0025 (17)0.0032 (17)
C250.022 (2)0.017 (2)0.017 (2)0.0014 (17)0.0014 (17)0.0042 (16)
C260.013 (2)0.014 (2)0.018 (2)0.0009 (17)0.0021 (18)0.0048 (19)
Geometric parameters (Å, º) top
C11—C11.476 (5)C14—C151.411 (7)
C1—N11.286 (5)C14—H140.95
C1—H10.95C16—C151.383 (5)
N1—N21.396 (5)C16—H160.95
N2—C21.358 (6)C15—H150.95
N2—H20.88C21—C261.397 (7)
C2—O21.233 (5)C21—C221.407 (5)
C2—C211.482 (5)C22—C231.387 (6)
C11—C161.381 (7)C22—I222.107 (4)
C11—C121.407 (6)C23—C241.386 (6)
C12—C131.391 (6)C23—H230.95
C12—N121.481 (5)C24—C251.386 (6)
N12—O221.220 (4)C24—H240.95
N12—O111.227 (4)C25—C261.403 (6)
C13—C141.384 (6)C25—H250.95
C13—H130.95C26—H260.95
C11—C1—N1118.3 (3)C11—C16—C15123.3 (6)
N1—C1—H1120.9C11—C16—H16118.3
C11—C1—H1120.9C15—C16—H16118.3
C1—N1—N2113.2 (3)C16—C15—C14118.7 (6)
N1—N2—C2119.1 (4)C16—C15—H15120.6
C2—N2—H2120.5C14—C15—H15120.6
N1—N2—H2120.5C26—C21—C22118.0 (4)
N2—C2—O2123.5 (4)C26—C21—C2118.9 (4)
O2—C2—C21122.2 (4)C22—C21—C2123.1 (4)
N2—C2—C21114.2 (3)C23—C22—C21121.2 (4)
C16—C11—C12116.3 (4)C23—C22—I22116.1 (3)
C16—C11—C1120.1 (4)C21—C22—I22122.6 (3)
C12—C11—C1123.3 (4)C24—C23—C22120.0 (4)
C13—C12—C11122.4 (4)C24—C23—H23120.0
C13—C12—N12117.0 (3)C22—C23—H23120.0
C11—C12—N12120.6 (4)C25—C24—C23120.3 (4)
O22—N12—O11124.1 (4)C25—C24—H24119.8
O22—N12—C12118.0 (3)C23—C24—H24119.8
O11—N12—C12117.8 (3)C24—C25—C26119.6 (4)
C14—C13—C12119.3 (4)C24—C25—H25120.2
C14—C13—H13120.4C26—C25—H25120.2
C12—C13—H13120.4C21—C26—C25120.9 (4)
C13—C14—C15119.8 (4)C21—C26—H26119.5
C13—C14—H14120.1C25—C26—H26119.5
C15—C14—H14120.1
C12—C11—C1—N1151.3 (4)C12—C11—C16—C151.6 (8)
C11—C1—N1—N2175.4 (3)C1—C11—C16—C15172.2 (5)
C1—N1—N2—C2174.4 (4)C11—C16—C15—C140.8 (10)
N1—N2—C2—O21.9 (6)C13—C14—C15—C161.7 (8)
N1—N2—C2—C21176.2 (3)O2—C2—C21—C26133.7 (5)
N2—C2—C21—C22138.2 (4)N2—C2—C21—C2644.4 (5)
N1—C1—C11—C1635.3 (6)O2—C2—C21—C2243.7 (6)
C16—C11—C12—C133.3 (6)C26—C21—C22—C230.5 (6)
C1—C11—C12—C13170.4 (4)C2—C21—C22—C23178.0 (4)
C16—C11—C12—N12173.9 (4)C26—C21—C22—I22175.7 (3)
C1—C11—C12—N1212.4 (6)C2—C21—C22—I226.9 (5)
C13—C12—N12—O2220.2 (5)C21—C22—C23—C240.1 (6)
C11—C12—N12—O22162.5 (4)I22—C22—C23—C24175.6 (3)
C13—C12—N12—O11158.7 (4)C22—C23—C24—C250.4 (6)
C11—C12—N12—O1118.6 (5)C23—C24—C25—C260.9 (6)
C11—C12—C13—C142.5 (6)C22—C21—C26—C251.1 (7)
N12—C12—C13—C14174.8 (4)C2—C21—C26—C25178.7 (4)
C12—C13—C14—C150.1 (6)C24—C25—C26—C211.3 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.881.982.820 (5)159
C1—H1···O2i0.952.273.082 (5)142
C26—H26···O22ii0.952.393.169 (6)139
Symmetry codes: (i) x, y1, z; (ii) x+1, y, z1/2.

Experimental details

Crystal data
Chemical formulaC14H10IN3O3
Mr395.15
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)120
a, b, c (Å)21.6122 (8), 5.0393 (2), 12.7868 (5)
V3)1392.62 (9)
Z4
Radiation typeMo Kα
µ (mm1)2.31
Crystal size (mm)0.28 × 0.08 × 0.05
Data collection
DiffractometerBruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.564, 0.893
No. of measured, independent and
observed [I > 2σ(I)] reflections
12100, 2783, 2579
Rint0.036
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.054, 1.05
No. of reflections2783
No. of parameters190
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.62, 0.64
Absolute structureFlack (1983), 1119 Friedel pairs
Absolute structure parameter0.01 (2)

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).

Selected geometric parameters (Å, º) top
C11—C11.476 (5)C2—O21.233 (5)
C1—N11.286 (5)C2—C211.482 (5)
N1—N21.396 (5)C22—I222.107 (4)
N2—C21.358 (6)
C11—C1—N1118.3 (3)N2—C2—O2123.5 (4)
C1—N1—N2113.2 (3)O2—C2—C21122.2 (4)
N1—N2—C2119.1 (4)N2—C2—C21114.2 (3)
C12—C11—C1—N1151.3 (4)N1—N2—C2—C21176.2 (3)
C11—C1—N1—N2175.4 (3)N2—C2—C21—C22138.2 (4)
C1—N1—N2—C2174.4 (4)C11—C12—N12—O1118.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.881.982.820 (5)159
C1—H1···O2i0.952.273.082 (5)142
C26—H26···O22ii0.952.393.169 (6)139
Symmetry codes: (i) x, y1, z; (ii) x+1, y, z1/2.
 

Acknowledgements

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

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science
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First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.
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First citationMcArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.
First citationOtwinowski, 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.
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
First citationSheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals

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