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

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

doi:10.1107/S0108270105017312

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 61| Part 7| July 2005| Pages o450-o451

doi:10.1107/S0108270105017312

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

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

^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 π–π stacking and iodo–nitro interactions are all absent.

Comment

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 π–π stacking interactions, and two- or three-centre iodo–nitro interactions. In the event, N—H⋯O and C—H⋯O hydrogen bonds and weak π–π 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 interbond 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, $[{1\over 2}]$ − y, $[{1\over 2}]$ + 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 = $[{1\over 4}]$ (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, $[{3\over 2}]$ − 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).

Two such sheets, related to one another by inversion, pass through each unit cell, and adjacent sheets are weakly linked by an aromatic π–π 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
The molecule of (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(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
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

Experimental

A sample of (I) 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
M_r = 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
D_x = 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
φ–ω scans
Absorption correction: multi-scan(SADABS; Bruker, 2000 )T_min = 0.374, T_max = 0.617
15459 measured reflections
4780 independent reflections
3011 reflections with I > 2σ(I)
R_int = 0.020
θ_max = 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(F_o²) + (0.0854P)² + 1.4841P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 2.61 e Å⁻³
Δρ_min = −2.27 e Å⁻³

Table 1
Selected torsion angles (°)

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, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 U_iso(H) values of 1.2U_eq(C,N).

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270105017312/sk1850sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270105017312/sk1850Isup2.hkl

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 π–π stacking interactions, and two- or three-centre iodo–nitro interactions. In the event, N—H···O and C—H···O hydrogen bonds and weak π–π stacking interactions are the only direction-specific intermolecular interactions present.

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 π–π 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.

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

	Fig. 1. The molecule of (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(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.
	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

C₁₃H₉IN₂O₃	F(000) = 712
M_r = 368.12	D_x = 1.842 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4780 reflections
a = 10.3792 (4) Å	θ = 2.1–32.5°
b = 13.6412 (6) Å	µ = 2.42 mm⁻¹
c = 9.8265 (4) Å	T = 298 K
β = 107.3830 (11)°	Prism, colourless
V = 1327.74 (9) Å³	0.48 × 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 tube	3011 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ–ω scans	θ_max = 32.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→15
T_min = 0.374, T_max = 0.617	k = −19→20
15459 measured reflections	l = −14→14

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.188	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0854P)² + 1.4841P] where P = (F_o² + 2F_c²)/3
4780 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 2.61 e Å⁻³
0 restraints	Δρ_min = −2.27 e Å⁻³

Crystal data top

C₁₃H₉IN₂O₃	V = 1327.74 (9) Å³
M_r = 368.12	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.3792 (4) Å	µ = 2.42 mm⁻¹
b = 13.6412 (6) Å	T = 298 K
c = 9.8265 (4) Å	0.48 × 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)
T_min = 0.374, T_max = 0.617	R_int = 0.020
15459 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.08	Δρ_max = 2.61 e Å⁻³
4780 reflections	Δρ_min = −2.27 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	0.54867 (3)	0.23220 (3)	0.54472 (5)	0.07976 (19)
O7	0.2184 (4)	0.2891 (2)	0.4439 (3)	0.0542 (7)
O41	0.0663 (5)	0.7571 (2)	0.7685 (4)	0.0740 (11)
O42	0.1173 (8)	0.7759 (2)	0.5753 (5)	0.1019 (17)
N1	0.2207 (3)	0.3224 (2)	0.6724 (3)	0.0399 (6)
N4	0.1031 (4)	0.7254 (2)	0.6709 (4)	0.0554 (9)
C1	0.1857 (3)	0.4226 (2)	0.6632 (3)	0.0357 (6)
C2	0.1528 (4)	0.4633 (3)	0.7792 (4)	0.0423 (7)
C3	0.1267 (4)	0.5627 (3)	0.7829 (4)	0.0454 (7)
C4	0.1306 (4)	0.6199 (2)	0.6685 (4)	0.0429 (7)
C5	0.1618 (4)	0.5812 (3)	0.5519 (4)	0.0491 (8)
C6	0.1904 (4)	0.4819 (3)	0.5492 (4)	0.0463 (8)
C7	0.2407 (4)	0.2642 (2)	0.5685 (4)	0.0381 (6)
C11	0.2943 (4)	0.1647 (2)	0.6181 (3)	0.0428 (7)
C12	0.4216 (5)	0.1362 (3)	0.6141 (4)	0.0544 (9)
C13	0.4691 (8)	0.0421 (4)	0.6559 (6)	0.089 (2)
C14	0.3866 (10)	−0.0233 (4)	0.6981 (6)	0.111 (3)
C15	0.2598 (9)	0.0037 (3)	0.7003 (6)	0.096 (2)
C16	0.2149 (6)	0.0985 (3)	0.6629 (5)	0.0645 (12)
H1	0.2376	0.2940	0.7529	0.048*
H2	0.1485	0.4234	0.8544	0.051*
H3	0.1069	0.5902	0.8609	0.054*
H5	0.1636	0.6213	0.4760	0.059*
H6	0.2124	0.4552	0.4720	0.056*
H13	0.5551	0.0234	0.6556	0.107*
H14	0.4174	−0.0864	0.7253	0.134*
H15	0.2044	−0.0413	0.7268	0.115*
H16	0.1305	0.1176	0.6680	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I12	0.0569 (2)	0.0849 (3)	0.0998 (3)	−0.00522 (15)	0.0269 (2)	−0.01773 (19)
O7	0.084 (2)	0.0449 (14)	0.0339 (12)	0.0146 (13)	0.0173 (12)	0.0004 (10)
O41	0.101 (3)	0.0484 (17)	0.069 (2)	0.0223 (17)	0.019 (2)	−0.0121 (15)
O42	0.197 (6)	0.0356 (17)	0.087 (3)	0.006 (2)	0.064 (3)	0.0098 (17)
N1	0.0587 (16)	0.0307 (12)	0.0325 (12)	0.0030 (11)	0.0170 (12)	0.0023 (10)
N4	0.074 (2)	0.0346 (15)	0.0497 (18)	0.0064 (14)	0.0063 (16)	−0.0050 (13)
C1	0.0423 (15)	0.0300 (13)	0.0347 (14)	−0.0003 (11)	0.0111 (12)	0.0006 (11)
C2	0.0559 (19)	0.0375 (16)	0.0355 (15)	0.0057 (14)	0.0167 (14)	0.0024 (12)
C3	0.0549 (19)	0.0421 (17)	0.0384 (16)	0.0070 (15)	0.0128 (14)	−0.0030 (13)
C4	0.0518 (18)	0.0307 (14)	0.0427 (16)	0.0016 (13)	0.0086 (14)	−0.0026 (12)
C5	0.072 (2)	0.0346 (16)	0.0423 (17)	0.0006 (16)	0.0203 (17)	0.0045 (14)
C6	0.070 (2)	0.0340 (15)	0.0397 (16)	0.0006 (15)	0.0228 (16)	0.0009 (13)
C7	0.0447 (16)	0.0371 (15)	0.0331 (14)	0.0005 (12)	0.0125 (12)	−0.0011 (12)
C11	0.062 (2)	0.0335 (15)	0.0324 (14)	0.0015 (14)	0.0138 (14)	−0.0039 (12)
C12	0.070 (2)	0.0445 (19)	0.0441 (18)	0.0147 (18)	0.0107 (17)	−0.0039 (15)
C13	0.131 (5)	0.068 (3)	0.067 (3)	0.054 (4)	0.025 (3)	0.009 (3)
C14	0.231 (9)	0.044 (3)	0.076 (3)	0.048 (4)	0.070 (5)	0.016 (2)
C15	0.200 (7)	0.037 (2)	0.072 (3)	−0.015 (3)	0.076 (4)	−0.004 (2)
C16	0.108 (4)	0.042 (2)	0.055 (2)	−0.009 (2)	0.043 (2)	−0.0054 (17)

Geometric parameters (Å, º) top

C1—C6	1.394 (4)	N1—H1	0.85
C1—C2	1.399 (4)	C7—O7	1.224 (4)
C1—N1	1.410 (4)	C7—C11	1.492 (5)
C2—C3	1.385 (5)	C11—C16	1.381 (6)
C2—H2	0.93	C11—C12	1.389 (6)
C3—C4	1.379 (5)	C12—C13	1.393 (6)
C3—H3	0.93	C12—I12	2.111 (5)
C4—C5	1.386 (5)	C13—C14	1.382 (11)
C4—N4	1.469 (4)	C13—H13	0.93
N4—O41	1.213 (6)	C14—C15	1.373 (11)
N4—O42	1.208 (5)	C14—H14	0.93
C5—C6	1.388 (5)	C15—C16	1.386 (7)
C5—H5	0.93	C15—H15	0.93
C6—H6	0.93	C16—H16	0.93
N1—C7	1.358 (4)

C6—C1—C2	120.0 (3)	C1—N1—H1	118.6
C6—C1—N1	123.0 (3)	O7—C7—N1	124.4 (3)
C2—C1—N1	117.0 (3)	O7—C7—C11	121.3 (3)
C3—C2—C1	120.5 (3)	N1—C7—C11	114.3 (3)
C3—C2—H2	119.7	C16—C11—C12	119.3 (4)
C1—C2—H2	119.7	C16—C11—C7	120.0 (4)
C4—C3—C2	118.6 (3)	C12—C11—C7	120.7 (3)
C4—C3—H3	120.7	C11—C12—C13	120.3 (5)
C2—C3—H3	120.7	C11—C12—I12	121.8 (3)
C3—C4—C5	121.9 (3)	C13—C12—I12	117.9 (4)
C3—C4—N4	119.3 (3)	C14—C13—C12	119.1 (6)
C5—C4—N4	118.8 (3)	C14—C13—H13	120.4
O41—N4—O42	123.5 (4)	C12—C13—H13	120.4
O41—N4—C4	118.1 (4)	C15—C14—C13	121.0 (5)
O42—N4—C4	118.4 (4)	C15—C14—H14	119.5
C4—C5—C6	119.5 (3)	C13—C14—H14	119.5
C4—C5—H5	120.3	C14—C15—C16	119.6 (6)
C6—C5—H5	120.3	C14—C15—H15	120.2
C5—C6—C1	119.5 (3)	C16—C15—H15	120.2
C5—C6—H6	120.3	C11—C16—C15	120.6 (5)
C1—C6—H6	120.3	C11—C16—H16	119.7
C7—N1—C1	127.8 (3)	C15—C16—H16	119.7
C7—N1—H1	113.4

C6—C1—C2—C3	−0.9 (6)	N1—C7—C11—C12	−115.4 (4)
N1—C1—C2—C3	175.4 (3)	C3—C4—N4—O41	−6.3 (6)
C1—C2—C3—C4	1.5 (6)	O7—C7—C11—C16	−112.9 (4)
C2—C3—C4—C5	−1.0 (6)	N1—C7—C11—C16	67.4 (5)
C2—C3—C4—N4	−180.0 (4)	O7—C7—C11—C12	64.3 (5)
C5—C4—N4—O41	174.7 (4)	C16—C11—C12—C13	−0.5 (6)
C3—C4—N4—O42	174.3 (5)	C7—C11—C12—C13	−177.8 (4)
C5—C4—N4—O42	−4.8 (7)	C16—C11—C12—I12	179.3 (3)
C3—C4—C5—C6	−0.1 (6)	C7—C11—C12—I12	2.0 (5)
N4—C4—C5—C6	178.9 (4)	C11—C12—C13—C14	1.6 (8)
C4—C5—C6—C1	0.7 (6)	I12—C12—C13—C14	−178.2 (5)
C2—C1—C6—C5	−0.2 (6)	C12—C13—C14—C15	−0.6 (10)
N1—C1—C6—C5	−176.3 (4)	C13—C14—C15—C16	−1.5 (9)
C6—C1—N1—C7	−12.2 (6)	C12—C11—C16—C15	−1.5 (6)
C1—N1—C7—O7	−7.3 (6)	C7—C11—C16—C15	175.7 (4)
C1—N1—C7—C11	172.4 (3)	C14—C15—C16—C11	2.5 (8)
C2—C1—N1—C7	171.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉IN₂O₃
M_r	368.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.3792 (4), 13.6412 (6), 9.8265 (4)
β (°)	107.3830 (11)
V (Å³)	1327.74 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.42
Crystal size (mm)	0.48 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.374, 0.617
No. of measured, independent and observed [I > 2σ(I)] reflections	15459, 4780, 3011
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.755

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.188, 1.08
No. of reflections	4780
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—C11	172.4 (3)	N1—C7—C11—C12	−115.4 (4)
C2—C1—N1—C7	171.6 (3)	C3—C4—N4—O41	−6.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, z+1/2; (ii) x, −y+3/2, z−1/2.

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

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
Bruker (1998). SMART. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2000). SADABS (Version 2.03) and SAINT (Version 6.02a). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. 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

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ISSN: 2053-2296

Volume 61| Part 7| July 2005| Pages o450-o451

doi:10.1107/S0108270105017312

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