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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

2-Iodo-N-(4-nitro­phen­yl)benzamide forms hydrogen-bonded sheets of R44(24) rings

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aInstituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil, bSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland, cDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and dInstituto 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 26 May 2005; accepted 1 June 2005; online 22 June 2005)

Mol­ecules of the title compound, C13H9IN2O3, are linked into C(4) chains by an N—H⋯O=C hydrogen bond, and these chains are linked into sheets of R44(24) rings by means of a C—H⋯O—N hydrogen bond. However, C—H⋯π(arene) hydrogen bonds, and ππ stacking and iodo–nitro inter­actions are all absent.

Comment

We report here the structure of the title compound, (I)[link] (Fig. 1[link]), which offers the possibility within a rather compact mol­ecular compass of a wide variety of potential inter­molecular inter­actions. These include N—H⋯O hydrogen bonds, with two possible types of O acceptor atom (viz. amide and nitro), C—H⋯O hydrogen bonds, likewise with two possible types of acceptor, C—H⋯π(arene) hydrogen bonds, aromatic ππ stacking inter­actions, and two- or three-centre iodo–nitro inter­actions. In the event, N—H⋯O and C—H⋯O hydrogen bonds and weak ππ stacking inter­actions are the only direction-specific inter­molecular inter­actions present.

[Scheme 1]

The mol­ecules of (I)[link] are nearly planar, apart from the iodinated ring, as shown by the leading torsion angles (Table 1[link]), and the amide group adopts the usual trans conformation; the bond lengths and interbond angles present no unusual values.

The supramolecular aggregation in (I)[link] is dominated by an N—H⋯O hydrogen bond, accompanied by a rather weaker C—H⋯O hydrogen bond (Table 2[link]). Amide atom N1 in the mol­ecule at (x, y, z) acts as a hydrogen-bond donor to amide atom O7 in the mol­ecule at (x, [{1\over 2}] − y, [{1\over 2}] + z), so forming a C(4) (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) chain running parallel to the [001] direction and generated by the c-glide plane at y = [{1\over 4}] (Fig. 2[link]). There are two chains of this type passing through each unit cell, one each in the domains 0.06 < x < 0.55 and 0.45 < x < 0.94. Within each domain, the chains related by translation along [010] are linked into sheets by means of the C—H⋯O hydrogen bond. Ar­yl atom C5 in the mol­ecule at (x, y, z) acts as a hydrogen-bond donor to nitro atom O41 in the mol­ecule at (x, [{3\over 2}] − y, −[{1\over 2}] + z), so forming a C(5) chain also running parallel to the [001] direction but this time generated by the c-glide plane at y = [{3\over 4}]. The combination of these two types of [001] chain generates a (100) sheet in the form of a (4,4)-net built from a single type of R44(24) ring (Fig. 3[link]).

Two such sheets, related to one another by inversion, pass through each unit cell, and adjacent sheets are weakly linked by an aromatic ππ stacking inter­action. The nitrated ar­yl rings in the mol­ecules at (x, y, z) and (−x, 1 − y, 1 − z), which lie in adjacent (100) sheets, are strictly parallel, with an inter­planar spacing of 3.521 (2) Å; the ring-centroid separation is 3.918 (2) Å, corresponding to a centroid offset of 1.719 (2) Å. In this way, each sheet is linked to the two neighbouring sheets.

[Figure 1]
Figure 1
The mol­ecule of (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 (I)[link], showing the formation of a C(4) chain along [001] built from N—H⋯O hydrogen bonds (dashed lines). For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, [{1\over 2}] − y, [{1\over 2}] + z) and (x, [{1\over 2}] − y, −[{1\over 2}] + z), respectively.
[Figure 3]
Figure 3
A stereoview of part of the crystal structure of (I)[link], showing the formation of a (100) sheet of R44(24) rings. Hydrogen bonds are shown as dashed lines. For clarity, H atoms not involved in the motifs shown have been omitted

Experimental

A sample of (I)[link] was prepared by reaction of 2-iodo­benzo­yl chloride with 4-nitro­aniline. Equimolar quantities (1 mmol) of the reagents were dissolved in chloroform (30 ml) and the mixture was heated under reflux for 1 h; the mixture was then cooled and the solvent removed. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in ethanol.

Crystal data
  • C13H9IN2O3

  • Mr = 368.12

  • Monoclinic, P 21 /c

  • a = 10.3792 (4) Å

  • b = 13.6412 (6) Å

  • c = 9.8265 (4) Å

  • β = 107.3830 (11)°

  • V = 1327.74 (9) Å3

  • Z = 4

  • Dx = 1.842 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 4780 reflections

  • θ = 2.1–32.5°

  • μ = 2.42 mm−1

  • T = 298 (2) K

  • Prism, colourless

  • 0.48 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • φω scans

  • Absorption correction: multi-scan(SADABS; Bruker, 2000[Bruker (2000). SADABS (Version 2.03) and SAINT (Version 6.02a). Bruker AXS Inc., Madison, Wisconsin, USA.])Tmin = 0.374, Tmax = 0.617

  • 15459 measured reflections

  • 4780 independent reflections

  • 3011 reflections with I > 2σ(I)

  • Rint = 0.020

  • θmax = 32.5°

  • h = −15 → 15

  • k = −19 → 20

  • l = −14 → 14

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.188

  • S = 1.08

  • 4780 reflections

  • 172 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0854P)2 + 1.4841P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 2.61 e Å−3

  • Δρmin = −2.27 e Å−3

Table 1
Selected torsion angles (°)[link]

C1—N1—C7—C11 172.4 (3)
C2—C1—N1—C7 171.6 (3)
N1—C7—C11—C12 −115.4 (4)
C3—C4—N4—O41 −6.3 (6)

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

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O7i 0.85 2.25 3.077 (4) 164
C5—H5⋯O41ii 0.93 2.59 3.457 (5) 156
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

The space group P21/c was uniquely assigned from the systematic absences. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.93 Å and an N—H distance of 0.85 Å, and with Uiso(H) values of 1.2Ueq(C,N).

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS (Version 2.03) and SAINT (Version 6.02a). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: 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

We report here the structure of the title compound, (I) (Fig. 1), which offers the possibility within a rather compact molecular compass of a wide variety of potential intermolecular interactions. These include N—H···O hydrogen bonds, with two possible types of O acceptor atom (viz. amide and nitro), C—H···O hydrogen bonds, likewise with two possible types of acceptor, C—H···π(arene) hydrogen bonds, aromatic ππ stacking interactions, and two- or three-centre iodo–nitro interactions. In the event, N—H···O and C—H···O hydrogen bonds and weak ππ stacking interactions are the only direction-specific intermolecular interactions present.

The molecules of (I) are nearly planar, apart from the iodinated ring, as shown by the leading torsion angles (Table 1), and the amide group adopts the usual trans conformation; the bond lengths and inter-bond angles present no unusual values.

The supramolecular aggregation in (I) is dominated by an N—H···O hydrogen bond, accompanied by a rather weaker C—H···O hydrogen bond (Table 2). Amide atom N1 in the molecule at (x, y, z) acts as a hydrogen-bond donor to amide atom O7 in the molecule at (x, 1/2 − y, 1/2 + z), so forming a C(4) (Bernstein et al., 1995) chain running parallel to the [001] direction and generated by the c-glide plane at y = 1/4 (Fig. 2). There are two chains of this type passing through each unit cell, one each in the domains 0.06 < x < 0.55 and 0.45 < x < 0.94. Within each domain, the chains related by translation along [010] are linked into sheets by means of the C—H···O hydrogen bond. Aryl atom C5 in the molecule at (x, y, z) acts as a hydrogen-bond donor to nitro atom O41 in the molecule at (x, 3/2 − y, −1/2 + z), so forming a C(5) chain also running parallel to the [001] direction but this time generated by the c-glide plane at y = 3/4. The combination of these two types of [001] chain generates a (100) sheet in the form of a (4,4)-net built from a single type of R44(24) ring (Fig. 3).

Two such sheets, related to one another by inversion, pass through each unit cell, and adjacent sheets are weakly linked by an aromatic ππ stacking interaction. The nitrated aryl rings in the molecules at (x, y, z) and (- x, 1 − y, 1 − z), which lie in adjacent (100) sheets, are strictly parallel, with an interplanar spacing of 3.521 (2) Å; the ring-centroid separation is 3.918 (2) Å, corresponding to a centroid offset of 1.719 (2) Å. In this way, each sheet is linked to the two neighbouring sheets.

Experimental top

A sample of (I) was prepared by reaction of 2-iodobenzoyl chloride with 4-nitroaniline. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in ethanol. Please specify quantitites of reagents/conditions.

Refinement top

The space group P21/c was uniquely assigned from the systematic absences. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.93 Å and an N—H distance of 0.85 Å, and with Uiso(H) values of 1.2Ueq(C,N).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: 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 (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 (I), showing the formation of a C(4) chain along [001] built from N—H···O hydrogen bonds (dashed lines). For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, 1/2 − y, 1/2 + z) and (x, 1/2 − y, −1/2 + z), respectively.
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of (I), showing the formation of a (100) sheet of R44(24) rings. Hydrogen bonds are shown as dashed lines. For clarity, H atoms not involved in the motifs shown have been omitted
2-Iodo-N-(4-nitrophenyl)benzamide top
Crystal data top
C13H9IN2O3F(000) = 712
Mr = 368.12Dx = 1.842 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4780 reflections
a = 10.3792 (4) Åθ = 2.1–32.5°
b = 13.6412 (6) ŵ = 2.42 mm1
c = 9.8265 (4) ÅT = 298 K
β = 107.3830 (11)°Prism, colourless
V = 1327.74 (9) Å30.48 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
4780 independent reflections
Radiation source: fine-focus sealed X-ray tube3011 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ϕω scansθmax = 32.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1515
Tmin = 0.374, Tmax = 0.617k = 1920
15459 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0854P)2 + 1.4841P]
where P = (Fo2 + 2Fc2)/3
4780 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 2.61 e Å3
0 restraintsΔρmin = 2.27 e Å3
Crystal data top
C13H9IN2O3V = 1327.74 (9) Å3
Mr = 368.12Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.3792 (4) ŵ = 2.42 mm1
b = 13.6412 (6) ÅT = 298 K
c = 9.8265 (4) Å0.48 × 0.25 × 0.20 mm
β = 107.3830 (11)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
4780 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
3011 reflections with I > 2σ(I)
Tmin = 0.374, Tmax = 0.617Rint = 0.020
15459 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.188H-atom parameters constrained
S = 1.08Δρmax = 2.61 e Å3
4780 reflectionsΔρmin = 2.27 e Å3
172 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I120.54867 (3)0.23220 (3)0.54472 (5)0.07976 (19)
O70.2184 (4)0.2891 (2)0.4439 (3)0.0542 (7)
O410.0663 (5)0.7571 (2)0.7685 (4)0.0740 (11)
O420.1173 (8)0.7759 (2)0.5753 (5)0.1019 (17)
N10.2207 (3)0.3224 (2)0.6724 (3)0.0399 (6)
N40.1031 (4)0.7254 (2)0.6709 (4)0.0554 (9)
C10.1857 (3)0.4226 (2)0.6632 (3)0.0357 (6)
C20.1528 (4)0.4633 (3)0.7792 (4)0.0423 (7)
C30.1267 (4)0.5627 (3)0.7829 (4)0.0454 (7)
C40.1306 (4)0.6199 (2)0.6685 (4)0.0429 (7)
C50.1618 (4)0.5812 (3)0.5519 (4)0.0491 (8)
C60.1904 (4)0.4819 (3)0.5492 (4)0.0463 (8)
C70.2407 (4)0.2642 (2)0.5685 (4)0.0381 (6)
C110.2943 (4)0.1647 (2)0.6181 (3)0.0428 (7)
C120.4216 (5)0.1362 (3)0.6141 (4)0.0544 (9)
C130.4691 (8)0.0421 (4)0.6559 (6)0.089 (2)
C140.3866 (10)0.0233 (4)0.6981 (6)0.111 (3)
C150.2598 (9)0.0037 (3)0.7003 (6)0.096 (2)
C160.2149 (6)0.0985 (3)0.6629 (5)0.0645 (12)
H10.23760.29400.75290.048*
H20.14850.42340.85440.051*
H30.10690.59020.86090.054*
H50.16360.62130.47600.059*
H60.21240.45520.47200.056*
H130.55510.02340.65560.107*
H140.41740.08640.72530.134*
H150.20440.04130.72680.115*
H160.13050.11760.66800.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I120.0569 (2)0.0849 (3)0.0998 (3)0.00522 (15)0.0269 (2)0.01773 (19)
O70.084 (2)0.0449 (14)0.0339 (12)0.0146 (13)0.0173 (12)0.0004 (10)
O410.101 (3)0.0484 (17)0.069 (2)0.0223 (17)0.019 (2)0.0121 (15)
O420.197 (6)0.0356 (17)0.087 (3)0.006 (2)0.064 (3)0.0098 (17)
N10.0587 (16)0.0307 (12)0.0325 (12)0.0030 (11)0.0170 (12)0.0023 (10)
N40.074 (2)0.0346 (15)0.0497 (18)0.0064 (14)0.0063 (16)0.0050 (13)
C10.0423 (15)0.0300 (13)0.0347 (14)0.0003 (11)0.0111 (12)0.0006 (11)
C20.0559 (19)0.0375 (16)0.0355 (15)0.0057 (14)0.0167 (14)0.0024 (12)
C30.0549 (19)0.0421 (17)0.0384 (16)0.0070 (15)0.0128 (14)0.0030 (13)
C40.0518 (18)0.0307 (14)0.0427 (16)0.0016 (13)0.0086 (14)0.0026 (12)
C50.072 (2)0.0346 (16)0.0423 (17)0.0006 (16)0.0203 (17)0.0045 (14)
C60.070 (2)0.0340 (15)0.0397 (16)0.0006 (15)0.0228 (16)0.0009 (13)
C70.0447 (16)0.0371 (15)0.0331 (14)0.0005 (12)0.0125 (12)0.0011 (12)
C110.062 (2)0.0335 (15)0.0324 (14)0.0015 (14)0.0138 (14)0.0039 (12)
C120.070 (2)0.0445 (19)0.0441 (18)0.0147 (18)0.0107 (17)0.0039 (15)
C130.131 (5)0.068 (3)0.067 (3)0.054 (4)0.025 (3)0.009 (3)
C140.231 (9)0.044 (3)0.076 (3)0.048 (4)0.070 (5)0.016 (2)
C150.200 (7)0.037 (2)0.072 (3)0.015 (3)0.076 (4)0.004 (2)
C160.108 (4)0.042 (2)0.055 (2)0.009 (2)0.043 (2)0.0054 (17)
Geometric parameters (Å, º) top
C1—C61.394 (4)N1—H10.85
C1—C21.399 (4)C7—O71.224 (4)
C1—N11.410 (4)C7—C111.492 (5)
C2—C31.385 (5)C11—C161.381 (6)
C2—H20.93C11—C121.389 (6)
C3—C41.379 (5)C12—C131.393 (6)
C3—H30.93C12—I122.111 (5)
C4—C51.386 (5)C13—C141.382 (11)
C4—N41.469 (4)C13—H130.93
N4—O411.213 (6)C14—C151.373 (11)
N4—O421.208 (5)C14—H140.93
C5—C61.388 (5)C15—C161.386 (7)
C5—H50.93C15—H150.93
C6—H60.93C16—H160.93
N1—C71.358 (4)
C6—C1—C2120.0 (3)C1—N1—H1118.6
C6—C1—N1123.0 (3)O7—C7—N1124.4 (3)
C2—C1—N1117.0 (3)O7—C7—C11121.3 (3)
C3—C2—C1120.5 (3)N1—C7—C11114.3 (3)
C3—C2—H2119.7C16—C11—C12119.3 (4)
C1—C2—H2119.7C16—C11—C7120.0 (4)
C4—C3—C2118.6 (3)C12—C11—C7120.7 (3)
C4—C3—H3120.7C11—C12—C13120.3 (5)
C2—C3—H3120.7C11—C12—I12121.8 (3)
C3—C4—C5121.9 (3)C13—C12—I12117.9 (4)
C3—C4—N4119.3 (3)C14—C13—C12119.1 (6)
C5—C4—N4118.8 (3)C14—C13—H13120.4
O41—N4—O42123.5 (4)C12—C13—H13120.4
O41—N4—C4118.1 (4)C15—C14—C13121.0 (5)
O42—N4—C4118.4 (4)C15—C14—H14119.5
C4—C5—C6119.5 (3)C13—C14—H14119.5
C4—C5—H5120.3C14—C15—C16119.6 (6)
C6—C5—H5120.3C14—C15—H15120.2
C5—C6—C1119.5 (3)C16—C15—H15120.2
C5—C6—H6120.3C11—C16—C15120.6 (5)
C1—C6—H6120.3C11—C16—H16119.7
C7—N1—C1127.8 (3)C15—C16—H16119.7
C7—N1—H1113.4
C6—C1—C2—C30.9 (6)N1—C7—C11—C12115.4 (4)
N1—C1—C2—C3175.4 (3)C3—C4—N4—O416.3 (6)
C1—C2—C3—C41.5 (6)O7—C7—C11—C16112.9 (4)
C2—C3—C4—C51.0 (6)N1—C7—C11—C1667.4 (5)
C2—C3—C4—N4180.0 (4)O7—C7—C11—C1264.3 (5)
C5—C4—N4—O41174.7 (4)C16—C11—C12—C130.5 (6)
C3—C4—N4—O42174.3 (5)C7—C11—C12—C13177.8 (4)
C5—C4—N4—O424.8 (7)C16—C11—C12—I12179.3 (3)
C3—C4—C5—C60.1 (6)C7—C11—C12—I122.0 (5)
N4—C4—C5—C6178.9 (4)C11—C12—C13—C141.6 (8)
C4—C5—C6—C10.7 (6)I12—C12—C13—C14178.2 (5)
C2—C1—C6—C50.2 (6)C12—C13—C14—C150.6 (10)
N1—C1—C6—C5176.3 (4)C13—C14—C15—C161.5 (9)
C6—C1—N1—C712.2 (6)C12—C11—C16—C151.5 (6)
C1—N1—C7—O77.3 (6)C7—C11—C16—C15175.7 (4)
C1—N1—C7—C11172.4 (3)C14—C15—C16—C112.5 (8)
C2—C1—N1—C7171.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O7i0.852.253.077 (4)164
C5—H5···O41ii0.932.593.457 (5)156
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC13H9IN2O3
Mr368.12
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)10.3792 (4), 13.6412 (6), 9.8265 (4)
β (°) 107.3830 (11)
V3)1327.74 (9)
Z4
Radiation typeMo Kα
µ (mm1)2.42
Crystal size (mm)0.48 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.374, 0.617
No. of measured, independent and
observed [I > 2σ(I)] reflections
15459, 4780, 3011
Rint0.020
(sin θ/λ)max1)0.755
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.188, 1.08
No. of reflections4780
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.61, 2.27

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected torsion angles (º) top
C1—N1—C7—C11172.4 (3)N1—C7—C11—C12115.4 (4)
C2—C1—N1—C7171.6 (3)C3—C4—N4—O416.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O7i0.852.253.077 (4)164
C5—H5···O41ii0.932.593.457 (5)156
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+3/2, z1/2.
 

Acknowledgements

X-ray data were collected at the University of Aberdeen; the authors thank the University of Aberdeen for funding the purchase of the diffractometer. JLW thanks CNPq and FAPERJ for financial support.

References

First citationBernstein, 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
First citationBruker (1998). SMART. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2000). SADABS (Version 2.03) and SAINT (Version 6.02a). Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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