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

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

(1RS,2RS)-N,N′-Bis(4-nitro­phenyl­methyl­ene)cyclo­hexane-1,2-di­amine: complex sheets built from C—H⋯O and C—H⋯π(arene) hydrogen bonds

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 29 July 2005; accepted 30 July 2005; online 20 August 2005)

The racemic title compound, C20H20N4O4, crystallizes with Z′ = 2 in the space group P21/c. Each independent mol­ecule exhibits approximate twofold rotation symmetry, but conformational differences between the mol­ecules preclude any higher symmetry. The mol­ecules are linked into complex sheets by a combination of four C—H⋯O hydrogen bonds and two C—H⋯π(arene) hydrogen bonds.

Comment

We have recently reported the structure of enantiopure (1R,2R)-N,N′-bis­(4-nitro­phenyl­methyl­ene)cyclo­hexane-1,2-­diamine, (I)[link] (Glidewell et al., 2005[Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. E61, o1699-o1701.]). This compound crystallizes with Z′ = 2 in space group C2, and the independent mol­ecules both exhibit approximate but not crystallographic twofold rotational symmetry. There is a single C—H⋯O hydrogen bond linking the two independent mol­ecules, but there are no other direction-specific inter­actions in the structure. In this paper, we report the structure of another isomeric form, the racemic 1RS,2RS compound, (II)[link].

Compound (II)[link] crystallizes in the centrosymmetric space group P21/c with Z′ = 2 (Fig. 1[link]). In the selected asymmetric unit each of the mol­ecules has the 1R,2R configuration, but the space group accommodates equal numbers of 1R,2R and 1S,2S enantiomers, as required by the racemic nature of (II)[link]. In each of the mol­ecules, the cyclo­hexane ring adopts a chain conformation, with the pendent substituent units in equatorial positions. Each mol­ecule adopts approximate, but not exact, twofold rotational symmetry, as shown by the leading torsion angles (Table 1[link]), and the differences between corresponding values for the two mol­ecules are sufficient to preclude any additional symmetry. The dihedral angles between the nitro groups containing N14X and N24X (X = A or B) and their adjacent aryl rings are 9.7 (2) and 3.3 (2)° in mol­ecule A, and 16.0 (2) and 12.0 (2)° in mol­ecule B.

[Scheme 1]

The mol­ecules of (II)[link] are linked into complex sheets by a combination of four C—H⋯O hydrogen bonds and two C—H⋯π(arene) hydrogen bonds (Table 2[link]), and the formation of the sheet is best approached in terms of the component sub-structures, each of which depends on a small subset of the hydrogen bonds.

The basic building blocks within the structure of (II)[link] are two centrosymmetric R22(32) dimers, formed by mol­ecules of types A and B, respectively; for the selected asymmetric unit, the type A dimer is centred at (0, 0, [{1\over 2}]) and the type B dimer is centred at ([{1\over 2}], [{1\over 2}], [{1\over 2}]). The overall structure can then be envisaged in terms of series of chains which result from the linking of these dimers. There are four such chains, two of which incorporate just one type of dimer, A or B, and the other two of which incorporate both types of dimer, A and B.

Within the asymmetric unit, aryl atom C22A acts as hydrogen-bond donor to nitro atom O15B, and propagation by inversion of this hydrogen bond links the two types of R22(32) dimer into a chain of rings running parallel to the [110] direction (Fig. 2[link]). In addition, aryl atom C27B, which lies in the type B dimer centred at ([{1\over 2}], [{1\over 2}], [{1\over 2}]), acts as hydrogen-bond donor to atom O24A at (x, 1 + y, z), which lies in the type A dimer centred at (0, 1, [{1\over 2}]), and propagation of this inter­action, again by inversion, links the R22(32) dimers into another chain of rings, this time running parallel to the [1[\overline{1}]0] direction (Fig. 3[link]).

Two further chains are generated by the linking of R22(32) dimers by means of C—H⋯π(arene) hydrogen bonds. These chains differ from those generated by C—H⋯O hydrogen bonds (Figs. 2[link] and 3[link]) only in that each type of chain involving C—H⋯π(arene) hydrogen bonds is built from just one type of mol­ecule. In the first of these, atom C4A in the type A mol­ecule at (x, y, z), part of the type A dimer centred at (0, 0, [{1\over 2}]), acts as hydrogen-bond donor, via atom H41A, to the C21A–C26A ring of the type A mol­ecule at (x, 1 + y, z), itself part of the type A dimer centred at (0, 1, [{1\over 2}]). Hence, a chain of dimers is formed along (0, y, [{1\over 2}]) (Fig. 4[link]). In the second chain of this type, atom C5B in the mol­ecule at (x, y, z), which is part of the type B dimer centred at ([{1\over 2}], [{1\over 2}], [{1\over 2}]), acts as hydrogen-bond donor, via atom H51B, to the C11B–C16B ring in the type B mol­ecule at (x, 1 + y, z), which forms part of the type B dimer centred at ([{1\over 2}], [{3\over 2}], [{1\over 2}]), so forming a chain of dimers along ([{1\over 2}], y, [{1\over 2}]) (Fig. 5[link]).

The combination of the [010], [110] and [1[\overline{1}]0] chains (Figs. 2[link]–5[link][link][link]) is sufficient to produce an (001) sheet lying in the domain 0.14 < z < 0.86 and generated by inversion centres at z = [{1\over 2}]. A second such sheet, related to the first by the translational symmetry, is generated by the centres of inversion at z = 1.0. There is one rather weak inter­action between mol­ecules in adjacent sheets, an approximately perpendicular nitro–nitro inter­action involving type B mol­ecules only. Atom O15B in the type B mol­ecule at (x, y, z), part of the sheet centred at z = [{1\over 2}], makes a short contact with atom O25B in the type B mol­ecule at (x, [{1\over 2}] − y, [{1\over 2}] + z), part of the sheet centred at z = 1.0, with O15B⋯O25Bi = 2.873 (2) Å, N14B—O15B⋯O25Bi = 86.4 (2)° and O15B⋯O25Bi—N24Bi = 135.9 (3)° [symmetry code: (i) x, [{1\over 2}] − y, [{1\over 2}] + z]. However, there are no significant ππ stacking inter­actions.

[Figure 1]
Figure 1
The 1R,2R enantiomers of the two independent mol­ecules in compound (II)[link], showing the atom-labelling schemes for (a) the type A mol­ecule and (b) the type B mol­ecule. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2]
Figure 2
A stereoview of part of the crystal structure of compound (II)[link], showing the linking of the R22(32) dimers of types A and B into a chain along [110]. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
[Figure 3]
Figure 3
A stereoview of part of the crystal structure of compound (II)[link], showing the linking of the R22(32) dimers of types A and B into a chain along [1[\overline{1}]0]. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
[Figure 4]
Figure 4
A stereoview of part of the crystal structure of compound (II)[link], showing the linking of R22(32) dimers of type A only into an [010] chain along (0, y, [{1\over 2}]). For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
[Figure 5]
Figure 5
A stereoview of part of the crystal structure of compound (II)[link], showing the linking of R22(32) dimers of type B only into an [010] chain along ([{1\over 2}], y, [{1\over 2}]). For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

Experimental

A mixture of racemic trans-­cyclo­hexane-1,2-diamine (0.228 g, 2 mmol) and 4-nitro­benzaldehyde (0.604 g, 4 mmol) in MeOH (30 ml) was heated under reflux for 30 min. The solution was then cooled to ambient temperature and the solvent was removed. The resulting solid was recrystallized from aqueous ethanol (1:1 v/v).

Crystal data
  • C20H20N4O4

  • Mr = 380.40

  • Monoclinic, P 21 /c

  • a = 22.4197 (5) Å

  • b = 8.9687 (2) Å

  • c = 21.2076 (4) Å

  • β = 117.7179 (11)°

  • V = 3774.99 (14) Å3

  • Z = 8

  • Dx = 1.339 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 8633 reflections

  • θ = 3.1–27.5°

  • μ = 0.10 mm−1

  • T = 120 (2) K

  • Block, yellow

  • 0.40 × 0.40 × 0.20 mm

Data collection
  • Bruker–Nonius KappaCCD area-detector 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 = 0.968, Tmax = 0.981

  • 43594 measured reflections

  • 8633 independent reflections

  • 6275 reflections with I > 2σ(I)

  • Rint = 0.043

  • θmax = 27.5°

  • h = −29 → 29

  • k = −10 → 11

  • l = −27 → 26

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.129

  • S = 1.06

  • 8633 reflections

  • 505 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0599P)2 + 1.1744P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Selected torsion angles (°)[link]

C2A—C1A—N1A—C17A 122.19 (14)
C1A—N1A—C17A—C11A 178.52 (13)
N1A—C17A—C11A—C12A 179.48 (15)
C13A—C14A—N14A—O14A 8.0 (2)
C1A—C2A—N2A—C27A 131.08 (14)
C2A—N2A—C27A—C21A 177.00 (13)
N2A—C27A—C21A—C26A −167.26 (14)
C23A—C24A—N24A—O24A 3.5 (2)
C2B—C1B—N1B—C17B 134.10 (14)
C1B—N1B—C17B—C11B 177.12 (12)
N1B—C17B—C11B—C12B −164.89 (14)
C13B—C14B—N14B—O14B 15.7 (2)
C1B—C2B—N2B—C27B 113.68 (15)
C2B—N2B—C27B—C21B 179.59 (13)
N2B—C27B—C21B—C26B −175.66 (15)
C23B—C24B—N24B—O24B 11.1 (2)

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

Cg1 and Cg2 are the centroids of rings C21A–C26A and C11B–C16B, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C22A—H22A⋯O15B 0.95 2.39 3.280 (2) 157
C25A—H25A⋯O15Ai 0.95 2.43 3.144 (2) 132
C13B—H13B⋯O24Bii 0.95 2.52 3.225 (2) 131
C27B—H27B⋯O24Aiii 0.95 2.35 3.167 (2) 143
C4A—H41ACg1iii 0.99 2.65 3.596 (2) 159
C5B—H51BCg2iii 0.99 2.56 3.515 (2) 161
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x, y+1, z.

The space group P21/c was uniquely assigned from the systematic absences. All H atoms were located in difference maps and were then treated as riding atoms, with C—H distances of 0.95 (aromatic and –CH=), 0.99 (CH2) or 1.00 Å (aliphatic CH), and with Uiso(H) = 1.2Ueq(C).

Data collection: COLLECT (Hooft, 1999[Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.]; Nonius, 1997[Nonius (1997). KappaCCD Server Software. Windows 3.11 Version. 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

We have recently reported the structure of enantiopure (1R,2R)-N,N'-bis(4-nitrophenylmethylene)-1,2-cyclohexanediamine, (I) (Glidewell et al., 2005). This compound crystallizes with Z' = 2 in space group C2, and the independent molecules both exhibit approximate but not crystallographic twofold rotational symmetry. There is a single C—H···O hydrogen bond linking the two independent molecules, but there are no other direction-specific interactions in the structure. In this paper, we report the structure of another isomeric form, the racemic (1RS,2RS) compound, (II).

Compound (II) crystallizes in the centrosymmetric space group P21/c with Z' = 2 (Fig. 1). In the selected asymmetric unit each of the molecules has the (1R,2R) configuration, but the space group accommodates equal numbers of (1R,2R) and (1S,2S) enantiomers, as required by the racemic nature of (II). In each of the molecules, the cyclohexane ring adopts a chain conformation, with the pendent substituent units in equatorial positions. Each molecule adopts approximate, but not exact, twofold rotational symmetry, as shown by the leading torsion angles (Table 1), and the differences between corresponding values for the two molecules are sufficient to preclude any additional symmetry. The dihedral angles between the nitro groups containing N14X and N24X (X = A or B) and their adjacent aryl rings are 9.7 (2) and 3.3 (2)° in molecule A, and 16.0 (2) and 12.0 (2)° in molecule B.

The molecules of (II) are linked into complex sheets by a combination of four C—H···O hydrogen bonds and two C—H···π(arene) hydrogen bonds (Table 2), and the formation of the sheet is best approached in terms of the component sub-structures, each of which depends on a small sub-set of the hydrogen bonds.

The basic building blocks within the structure of (II) are two centrosymmetric R22(32) dimers, formed by molecules of types A and B respectively; for the selected asymmetric unit, the type A dimer is centred at (0, 0, 1/2) and the type B dimer is centred at (1/2, 1/2, 1/2). The overall structure can then be envisaged in terms of series of chains which result from the linking of these dimers. There are four such chains, two of which incorporate just one type of dimer, A or B, and the other two of which incorporate both types of dimer, A and B.

Within the asymmetric unit, aryl atom C22A acts as hydrogen-bond donor to nitro atom O15B, and propagation by inversion of this hydrogen bond links the two types of R22(32) dimer into a chain of rings running parallel to the [110] direction (Fig. 2). In addition, aryl atom C27B, which lies in the type B dimer centred at (1/2,1/2,1/2), acts as hydrogen-bond donor to atom O24A at (x, 1 + y, z), which lies in the type A dimer centred at (0, 1, 1/2), and propagation of this interaction, again by inversion, links the R22(32) dimers into another chain of rings, this time running parallel to the [110] direction (Fig. 3).

Two further chains are generated by the linking of R22(32) dimers by means of C—H···π(arene) hydrogen bonds. These chains differ from those generated by C—H···O hydrogen bonds (Figs. 2 and 3) only in that each type of chain involving C—H···π(arene) hydrogen bonds is built from just one type of molecule. In the first of these, atom C4A in the type A molecule at (x, y, z), part of the type A dimer centred at (0, 0, 1/2), acts as hydrogen-bond donor, via atom H41A, to the C21A–C26A ring of the type A molecule at (x, 1 + y, z), itself part of the type A dimer centred at (0, 1, 1/2). Hence, a chain of dimers is formed along (0, y, 1/2) (Fig. 4). In the second chain of this type, atom C5B in the molecule at (x, y, z), which is part of the type B dimer centred at (1/2, 1/2, 1/2), acts as hydrogen-bond donor, via atom H51B, to the C11B–C16B ring in the type 2 [type B?] molecule at (x, 1 + y, z), which forms part of the type B dimer centred at (1/2, 3/2, 1/2), so forming a chain of dimers along (1/2, y, 1/2) (Fig. 5).

The combination of the [010], [110] and [110] chains (Figs. 2–5) is sufficient to produce an (001) sheet lying in the domain 0.14 < z < 0.86 and generated by inversion centres at z = 1/2. A second such sheet, related to the first by the translational symmetry, is generated by the centres of inversion at z = 1.0. There is one rather weak interaction between molecules in adjacent sheets, an approximately perpendicular nitro···nitro interaction involving type B molecules only. Atom O15B in the type B molecule at (x, y, z), part of the sheet centred at z = 1/2, makes a short contact with atom O25B in the type B molecule at (x, 1/2 − y, 1/2 + z), part of the sheet centred at z = 1.0, with O15B···O25Bi 2.873 (2) Å, N14B—O15B···O25Bi 86.4 (2)° and O15B···O25Bi—N24Bi 135.9 (3)° [symmetry code: (i) x, 1/2 − y, 1/2 + z]. However, there are no significant ππ stacking interactions.

Experimental top

A mixture of racemic trans-1,2-diaminocyclohexane (0.228 g, 2 mmol) and 4-nitrobenzaldehyde (0.604 g, 4 mmol) in MeOH (30 ml) was heated under reflux for 30 min. The solution was then cooled to ambient temperature and the solvent was removed. The resulting solid was recrystallized from aqueous ethanol [Solvent ratio?].

Refinement top

The space group P21/c was uniquely assigned from the systematic absences. All H atoms were located in difference maps and were then treated as riding atoms, with C—H distances of 0.95 (aromatic and –CH), 0.99 (CH2) or 1.00 Å (aliphatic CH), and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: COLLECT (Hooft, 1999; Nonius, 1997); 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 (1R,2R) enantiomers of the two independent molecules in compound (II), showing the atom-labelling scheme. (a) The type A molecule. (b) The type B molecule. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A stereoview of part of the crystal structure of compound (II), showing the linking of the R22(32) dimers of types A and B into a chain along [110]. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of compound (II), showing the linking of the R22(32) dimers of types A and B into a chain along [110]. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
[Figure 4] Fig. 4. A stereoview of part of the crystal structure of compound (II), showing the linking of R22(32) dimers of type A only into an [010] chain along (0, y, 1/2). For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
[Figure 5] Fig. 5. A stereoview of part of the crystal structure of compound (II), showing the linking of R22(32) dimers of type B only into an [010] chain along (1/2, y, 1/2). For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
(1RS,2RS)-N,N'-Bis(4-nitrophenylmethylene)cyclohexane-1,2-diamine top
Crystal data top
C20H20N4O4F(000) = 1600
Mr = 380.40Dx = 1.339 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8633 reflections
a = 22.4197 (5) Åθ = 3.1–27.5°
b = 8.9687 (2) ŵ = 0.10 mm1
c = 21.2076 (4) ÅT = 120 K
β = 117.7179 (11)°Block, yellow
V = 3774.99 (14) Å30.40 × 0.40 × 0.20 mm
Z = 8
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
8633 independent reflections
Radiation source: Bruker Nonius FR91 rotating anode6275 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ϕ and ω scansh = 2929
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1011
Tmin = 0.968, Tmax = 0.981l = 2726
43594 measured reflections
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0599P)2 + 1.1744P]
where P = (Fo2 + 2Fc2)/3
8633 reflections(Δ/σ)max < 0.001
505 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C20H20N4O4V = 3774.99 (14) Å3
Mr = 380.40Z = 8
Monoclinic, P21/cMo Kα radiation
a = 22.4197 (5) ŵ = 0.10 mm1
b = 8.9687 (2) ÅT = 120 K
c = 21.2076 (4) Å0.40 × 0.40 × 0.20 mm
β = 117.7179 (11)°
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
8633 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
6275 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.981Rint = 0.043
43594 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 1.06Δρmax = 0.37 e Å3
8633 reflectionsΔρmin = 0.29 e Å3
505 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.12439 (8)0.65843 (17)0.57608 (8)0.0238 (3)
C2A0.08905 (8)0.64452 (17)0.49470 (8)0.0228 (3)
C3A0.10054 (8)0.78506 (18)0.46075 (8)0.0260 (3)
C4A0.07787 (8)0.92517 (18)0.48457 (9)0.0291 (4)
C5A0.11318 (9)0.93827 (19)0.56531 (9)0.0305 (4)
C6A0.10135 (8)0.79910 (19)0.59924 (8)0.0290 (4)
N1A0.10892 (6)0.52650 (15)0.60632 (7)0.0251 (3)
C17A0.15854 (8)0.45096 (18)0.64966 (8)0.0248 (3)
C11A0.15159 (8)0.31692 (18)0.68609 (8)0.0235 (3)
C12A0.20948 (8)0.2404 (2)0.73262 (9)0.0324 (4)
C13A0.20560 (9)0.1216 (2)0.77225 (9)0.0330 (4)
C14A0.14332 (8)0.08000 (17)0.76412 (8)0.0258 (3)
C15A0.08458 (8)0.14839 (18)0.71549 (8)0.0261 (3)
C16A0.08913 (8)0.26760 (18)0.67681 (8)0.0255 (3)
N14A0.13969 (8)0.03789 (15)0.81064 (7)0.0310 (3)
O14A0.19249 (7)0.08221 (15)0.85972 (7)0.0471 (4)
O15A0.08384 (7)0.08285 (13)0.79903 (6)0.0378 (3)
N2A0.11647 (6)0.51612 (14)0.47447 (7)0.0239 (3)
C27A0.07493 (8)0.42526 (17)0.43048 (8)0.0242 (3)
C21A0.09677 (8)0.29509 (18)0.40343 (8)0.0244 (3)
C22A0.16417 (8)0.25086 (18)0.43447 (9)0.0279 (4)
C23A0.18415 (8)0.13115 (18)0.40749 (9)0.0305 (4)
C24A0.13515 (8)0.05873 (18)0.34797 (9)0.0273 (4)
C25A0.06827 (8)0.09872 (18)0.31657 (8)0.0284 (4)
C26A0.04881 (8)0.21691 (18)0.34490 (8)0.0272 (3)
N24A0.15571 (8)0.06346 (16)0.31586 (9)0.0364 (4)
O24A0.21514 (7)0.10102 (16)0.34537 (9)0.0590 (4)
O25A0.11288 (8)0.12053 (15)0.26099 (7)0.0473 (4)
C1B0.40661 (8)1.14498 (17)0.48900 (8)0.0223 (3)
C2B0.37930 (8)1.16469 (17)0.40844 (8)0.0233 (3)
C3B0.40644 (8)1.30649 (19)0.39150 (8)0.0287 (4)
C4B0.39238 (8)1.44351 (18)0.42503 (8)0.0288 (4)
C5B0.42068 (8)1.42341 (18)0.50497 (8)0.0267 (3)
C6B0.39173 (8)1.28348 (18)0.52136 (8)0.0253 (3)
N1B0.37422 (6)1.01572 (14)0.50188 (6)0.0236 (3)
C17B0.41195 (8)0.92504 (17)0.54935 (8)0.0245 (3)
C11B0.38543 (8)0.79367 (17)0.56999 (8)0.0240 (3)
C12B0.42774 (8)0.72089 (18)0.63335 (8)0.0261 (3)
C13B0.40450 (8)0.60050 (18)0.65666 (8)0.0262 (3)
C14B0.33964 (8)0.55215 (17)0.61478 (8)0.0251 (3)
C15B0.29633 (8)0.61897 (18)0.55044 (8)0.0264 (3)
C16B0.31980 (8)0.74171 (18)0.52884 (8)0.0264 (3)
N14B0.31482 (7)0.42484 (15)0.64020 (7)0.0290 (3)
O14B0.34670 (7)0.38938 (14)0.70303 (6)0.0426 (3)
O15B0.26294 (6)0.36263 (13)0.59769 (7)0.0354 (3)
N2B0.39917 (6)1.03448 (15)0.38062 (7)0.0253 (3)
C27B0.35191 (8)0.95079 (18)0.33889 (8)0.0253 (3)
C21B0.36323 (8)0.81585 (18)0.30588 (8)0.0240 (3)
C22B0.42762 (8)0.76914 (18)0.32069 (8)0.0252 (3)
C23B0.43645 (8)0.64767 (18)0.28605 (8)0.0259 (3)
C24B0.37982 (8)0.57521 (17)0.23515 (8)0.0239 (3)
C25B0.31539 (8)0.61660 (19)0.22036 (9)0.0296 (4)
C26B0.30758 (8)0.73661 (19)0.25688 (9)0.0305 (4)
N24B0.38834 (7)0.45423 (15)0.19303 (7)0.0286 (3)
O24B0.44525 (6)0.40587 (15)0.21158 (7)0.0443 (3)
O25B0.33848 (6)0.41029 (14)0.14043 (6)0.0373 (3)
H1A0.17420.66370.59370.029*
H2A0.03960.62990.47720.027*
H31A0.14900.79360.47420.031*
H32A0.07520.77650.40820.031*
H41A0.08821.01410.46370.035*
H42A0.02850.92150.46690.035*
H51A0.09591.02680.57960.037*
H52A0.16210.95200.58260.037*
H61A0.05280.79070.58540.035*
H62A0.12630.80830.65170.035*
H17A0.20250.48180.65930.030*
H12A0.25200.26990.73720.039*
H13A0.24510.06980.80440.040*
H15A0.04200.11400.70880.031*
H16A0.04930.31650.64350.031*
H27A0.02810.44090.41420.029*
H22A0.19670.30350.47460.033*
H23A0.22980.09960.42900.037*
H25A0.03600.04620.27620.034*
H26A0.00270.24480.32440.033*
H1B0.45641.12840.51170.027*
H2B0.32901.17020.38530.028*
H31B0.38531.31990.33920.034*
H32B0.45571.29650.40940.034*
H41B0.41311.53230.41540.035*
H42B0.34321.46030.40330.035*
H51B0.40931.51160.52540.032*
H52B0.47041.41530.52730.032*
H61B0.34241.29490.50200.030*
H62B0.41151.27090.57360.030*
H17B0.45920.94220.57260.029*
H12B0.47280.75410.66080.031*
H13B0.43270.55260.70050.031*
H15B0.25210.58180.52220.032*
H16B0.29090.79090.48560.032*
H27B0.30700.97580.32830.030*
H22B0.46580.82140.35500.030*
H23B0.48040.61430.29680.031*
H25B0.27730.56410.18600.036*
H26B0.26370.76520.24840.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0252 (8)0.0229 (8)0.0249 (8)0.0012 (6)0.0130 (7)0.0035 (6)
C2A0.0235 (8)0.0213 (8)0.0252 (8)0.0034 (6)0.0125 (6)0.0021 (6)
C3A0.0302 (8)0.0256 (9)0.0258 (8)0.0048 (7)0.0160 (7)0.0046 (7)
C4A0.0332 (9)0.0228 (9)0.0341 (9)0.0041 (7)0.0180 (7)0.0052 (7)
C5A0.0363 (9)0.0227 (9)0.0352 (9)0.0018 (7)0.0189 (8)0.0023 (7)
C6A0.0359 (9)0.0283 (9)0.0252 (8)0.0020 (7)0.0163 (7)0.0008 (7)
N1A0.0290 (7)0.0258 (7)0.0223 (6)0.0020 (6)0.0134 (6)0.0030 (6)
C17A0.0265 (8)0.0270 (9)0.0233 (8)0.0009 (6)0.0136 (7)0.0001 (6)
C11A0.0285 (8)0.0232 (8)0.0194 (7)0.0021 (6)0.0118 (6)0.0014 (6)
C12A0.0267 (8)0.0337 (10)0.0337 (9)0.0033 (7)0.0115 (7)0.0055 (7)
C13A0.0302 (9)0.0312 (10)0.0308 (9)0.0079 (7)0.0084 (7)0.0076 (7)
C14A0.0372 (9)0.0188 (8)0.0201 (7)0.0031 (7)0.0121 (7)0.0000 (6)
C15A0.0279 (8)0.0249 (9)0.0252 (8)0.0009 (7)0.0121 (7)0.0002 (7)
C16A0.0272 (8)0.0263 (9)0.0207 (7)0.0037 (7)0.0092 (6)0.0033 (6)
N14A0.0449 (9)0.0211 (7)0.0260 (7)0.0046 (6)0.0156 (7)0.0019 (6)
O14A0.0520 (8)0.0424 (8)0.0379 (7)0.0137 (7)0.0134 (7)0.0189 (6)
O15A0.0517 (8)0.0291 (7)0.0339 (6)0.0054 (6)0.0210 (6)0.0021 (5)
N2A0.0285 (7)0.0214 (7)0.0241 (6)0.0024 (5)0.0141 (6)0.0025 (5)
C27A0.0260 (8)0.0241 (8)0.0246 (8)0.0014 (6)0.0135 (7)0.0042 (6)
C21A0.0308 (8)0.0209 (8)0.0271 (8)0.0012 (6)0.0181 (7)0.0033 (6)
C22A0.0298 (9)0.0238 (9)0.0311 (8)0.0040 (7)0.0149 (7)0.0024 (7)
C23A0.0297 (9)0.0248 (9)0.0433 (10)0.0026 (7)0.0222 (8)0.0021 (7)
C24A0.0394 (9)0.0191 (8)0.0352 (9)0.0060 (7)0.0273 (8)0.0028 (7)
C25A0.0362 (9)0.0259 (9)0.0257 (8)0.0076 (7)0.0167 (7)0.0011 (7)
C26A0.0290 (8)0.0270 (9)0.0271 (8)0.0017 (7)0.0142 (7)0.0036 (7)
N24A0.0518 (10)0.0235 (8)0.0520 (10)0.0100 (7)0.0393 (8)0.0063 (7)
O24A0.0492 (9)0.0436 (9)0.1044 (13)0.0092 (7)0.0527 (9)0.0286 (8)
O25A0.0752 (10)0.0316 (7)0.0406 (7)0.0065 (7)0.0315 (8)0.0111 (6)
C1B0.0227 (7)0.0229 (8)0.0228 (7)0.0018 (6)0.0117 (6)0.0008 (6)
C2B0.0242 (8)0.0233 (8)0.0228 (7)0.0014 (6)0.0113 (6)0.0028 (6)
C3B0.0320 (9)0.0311 (9)0.0245 (8)0.0033 (7)0.0145 (7)0.0025 (7)
C4B0.0278 (8)0.0235 (9)0.0330 (9)0.0032 (7)0.0125 (7)0.0024 (7)
C5B0.0282 (8)0.0227 (8)0.0301 (8)0.0035 (6)0.0143 (7)0.0048 (7)
C6B0.0284 (8)0.0254 (9)0.0252 (8)0.0022 (6)0.0150 (7)0.0025 (7)
N1B0.0288 (7)0.0211 (7)0.0239 (6)0.0028 (5)0.0148 (6)0.0022 (5)
C17B0.0270 (8)0.0237 (8)0.0244 (8)0.0013 (6)0.0134 (7)0.0043 (6)
C11B0.0316 (8)0.0189 (8)0.0262 (8)0.0018 (6)0.0174 (7)0.0024 (6)
C12B0.0279 (8)0.0258 (9)0.0248 (8)0.0004 (7)0.0124 (7)0.0042 (7)
C13B0.0345 (9)0.0238 (8)0.0205 (7)0.0075 (7)0.0128 (7)0.0007 (6)
C14B0.0350 (9)0.0184 (8)0.0298 (8)0.0014 (6)0.0216 (7)0.0019 (6)
C15B0.0256 (8)0.0241 (8)0.0301 (8)0.0008 (6)0.0134 (7)0.0033 (7)
C16B0.0290 (8)0.0236 (8)0.0258 (8)0.0048 (6)0.0122 (7)0.0024 (7)
N14B0.0395 (8)0.0221 (7)0.0309 (8)0.0009 (6)0.0209 (7)0.0009 (6)
O14B0.0682 (9)0.0338 (7)0.0255 (6)0.0094 (6)0.0216 (6)0.0005 (5)
O15B0.0320 (7)0.0281 (7)0.0446 (7)0.0025 (5)0.0165 (6)0.0030 (5)
N2B0.0293 (7)0.0266 (7)0.0222 (6)0.0007 (6)0.0137 (6)0.0014 (5)
C27B0.0266 (8)0.0254 (9)0.0260 (8)0.0008 (6)0.0140 (7)0.0007 (7)
C21B0.0288 (8)0.0232 (8)0.0217 (7)0.0026 (6)0.0133 (7)0.0012 (6)
C22B0.0263 (8)0.0277 (9)0.0195 (7)0.0031 (6)0.0088 (6)0.0018 (6)
C23B0.0249 (8)0.0290 (9)0.0235 (8)0.0012 (6)0.0111 (7)0.0009 (7)
C24B0.0325 (8)0.0195 (8)0.0218 (7)0.0017 (6)0.0144 (7)0.0004 (6)
C25B0.0266 (8)0.0275 (9)0.0301 (8)0.0067 (7)0.0093 (7)0.0059 (7)
C26B0.0256 (8)0.0278 (9)0.0378 (9)0.0025 (7)0.0146 (7)0.0049 (7)
N24B0.0357 (8)0.0245 (7)0.0274 (7)0.0043 (6)0.0161 (6)0.0032 (6)
O24B0.0364 (7)0.0466 (8)0.0480 (8)0.0046 (6)0.0181 (6)0.0164 (6)
O25B0.0425 (7)0.0322 (7)0.0328 (6)0.0099 (6)0.0138 (6)0.0108 (5)
Geometric parameters (Å, º) top
C1A—N1A1.4623 (19)C1B—N1B1.4596 (19)
C1A—C6A1.528 (2)C1B—C6B1.529 (2)
C1A—C2A1.533 (2)C1B—C2B1.534 (2)
C1A—H1A1.00C1B—H1B1.00
C2A—N2A1.4606 (19)C2B—N2B1.468 (2)
C2A—C3A1.532 (2)C2B—C3B1.523 (2)
C2A—H2A1.00C2B—H2B1.00
C3A—C4A1.527 (2)C3B—C4B1.524 (2)
C3A—H31A0.99C3B—H31B0.99
C3A—H32A0.99C3B—H32B0.99
C4A—C5A1.520 (2)C4B—C5B1.519 (2)
C4A—H41A0.99C4B—H41B0.99
C4A—H42A0.99C4B—H42B0.99
C5A—C6A1.524 (2)C5B—C6B1.525 (2)
C5A—H51A0.99C5B—H51B0.99
C5A—H52A0.99C5B—H52B0.99
C6A—H61A0.99C6B—H61B0.99
C6A—H62A0.99C6B—H62B0.99
N1A—C17A1.261 (2)N1B—C17B1.264 (2)
C17A—C11A1.476 (2)C17B—C11B1.475 (2)
C17A—H17A0.95C17B—H17B0.95
C11A—C12A1.392 (2)C11B—C12B1.395 (2)
C11A—C16A1.392 (2)C11B—C16B1.396 (2)
C12A—C13A1.385 (2)C12B—C13B1.386 (2)
C12A—H12A0.95C12B—H12B0.95
C13A—C14A1.376 (2)C13B—C14B1.375 (2)
C13A—H13A0.95C13B—H13B0.95
C14A—C15A1.382 (2)C14B—C15B1.390 (2)
C14A—N14A1.474 (2)C14B—N14B1.478 (2)
C15A—C16A1.380 (2)C15B—C16B1.387 (2)
C15A—H15A0.95C15B—H15B0.95
C16A—H16A0.95C16B—H16B0.95
N14A—O14A1.2233 (18)N14B—O14B1.2253 (18)
N14A—O15A1.2266 (18)N14B—O15B1.2254 (18)
N2A—C27A1.262 (2)N2B—C27B1.264 (2)
C27A—C21A1.481 (2)C27B—C21B1.478 (2)
C27A—H27A0.95C27B—H27B0.95
C21A—C26A1.395 (2)C21B—C26B1.391 (2)
C21A—C22A1.396 (2)C21B—C22B1.391 (2)
C22A—C23A1.385 (2)C22B—C23B1.379 (2)
C22A—H22A0.95C22B—H22B0.95
C23A—C24A1.390 (2)C23B—C24B1.387 (2)
C23A—H23A0.95C23B—H23B0.95
C24A—C25A1.375 (2)C24B—C25B1.379 (2)
C24A—N24A1.473 (2)C24B—N24B1.473 (2)
C25A—C26A1.385 (2)C25B—C26B1.384 (2)
C25A—H25A0.95C25B—H25B0.95
C26A—H26A0.95C26B—H26B0.95
N24A—O25A1.2243 (19)N24B—O25B1.2205 (17)
N24A—O24A1.227 (2)N24B—O24B1.2262 (18)
N1A—C1A—C6A110.03 (12)N1B—C1B—C6B109.25 (11)
N1A—C1A—C2A108.91 (12)N1B—C1B—C2B108.93 (12)
C6A—C1A—C2A110.74 (12)C6B—C1B—C2B110.42 (12)
N1A—C1A—H1A109.0N1B—C1B—H1B109.4
C6A—C1A—H1A109.0C6B—C1B—H1B109.4
C2A—C1A—H1A109.0C2B—C1B—H1B109.4
N2A—C2A—C3A108.96 (11)N2B—C2B—C3B109.89 (12)
N2A—C2A—C1A109.10 (12)N2B—C2B—C1B108.51 (12)
C3A—C2A—C1A110.52 (13)C3B—C2B—C1B111.26 (12)
N2A—C2A—H2A109.4N2B—C2B—H2B109.0
C3A—C2A—H2A109.4C3B—C2B—H2B109.0
C1A—C2A—H2A109.4C1B—C2B—H2B109.0
C4A—C3A—C2A111.53 (12)C2B—C3B—C4B111.79 (12)
C4A—C3A—H31A109.3C2B—C3B—H31B109.3
C2A—C3A—H31A109.3C4B—C3B—H31B109.3
C4A—C3A—H32A109.3C2B—C3B—H32B109.3
C2A—C3A—H32A109.3C4B—C3B—H32B109.3
H31A—C3A—H32A108.0H31B—C3B—H32B107.9
C5A—C4A—C3A110.92 (13)C5B—C4B—C3B110.81 (13)
C5A—C4A—H41A109.5C5B—C4B—H41B109.5
C3A—C4A—H41A109.5C3B—C4B—H41B109.5
C5A—C4A—H42A109.5C5B—C4B—H42B109.5
C3A—C4A—H42A109.5C3B—C4B—H42B109.5
H41A—C4A—H42A108.0H41B—C4B—H42B108.1
C4A—C5A—C6A110.77 (14)C4B—C5B—C6B110.53 (13)
C4A—C5A—H51A109.5C4B—C5B—H51B109.5
C6A—C5A—H51A109.5C6B—C5B—H51B109.5
C4A—C5A—H52A109.5C4B—C5B—H52B109.5
C6A—C5A—H52A109.5C6B—C5B—H52B109.5
H51A—C5A—H52A108.1H51B—C5B—H52B108.1
C5A—C6A—C1A111.42 (12)C5B—C6B—C1B111.18 (12)
C5A—C6A—H61A109.3C5B—C6B—H61B109.4
C1A—C6A—H61A109.3C1B—C6B—H61B109.4
C5A—C6A—H62A109.3C5B—C6B—H62B109.4
C1A—C6A—H62A109.3C1B—C6B—H62B109.4
H61A—C6A—H62A108.0H61B—C6B—H62B108.0
C17A—N1A—C1A116.47 (13)C17B—N1B—C1B116.94 (13)
N1A—C17A—C11A123.16 (14)N1B—C17B—C11B122.50 (14)
N1A—C17A—H17A118.4N1B—C17B—H17B118.7
C11A—C17A—H17A118.4C11B—C17B—H17B118.7
C12A—C11A—C16A119.23 (15)C12B—C11B—C16B119.52 (15)
C12A—C11A—C17A118.81 (14)C12B—C11B—C17B118.19 (14)
C16A—C11A—C17A121.93 (14)C16B—C11B—C17B122.29 (14)
C13A—C12A—C11A120.56 (15)C13B—C12B—C11B120.54 (15)
C13A—C12A—H12A119.7C13B—C12B—H12B119.7
C11A—C12A—H12A119.7C11B—C12B—H12B119.7
C14A—C13A—C12A118.62 (15)C14B—C13B—C12B118.38 (14)
C14A—C13A—H13A120.7C14B—C13B—H13B120.8
C12A—C13A—H13A120.7C12B—C13B—H13B120.8
C13A—C14A—C15A122.15 (15)C13B—C14B—C15B122.99 (15)
C13A—C14A—N14A118.62 (14)C13B—C14B—N14B118.20 (14)
C15A—C14A—N14A119.19 (14)C15B—C14B—N14B118.80 (14)
C16A—C15A—C14A118.63 (15)C16B—C15B—C14B117.87 (15)
C16A—C15A—H15A120.7C16B—C15B—H15B121.1
C14A—C15A—H15A120.7C14B—C15B—H15B121.1
C15A—C16A—C11A120.64 (15)C15B—C16B—C11B120.66 (14)
C15A—C16A—H16A119.7C15B—C16B—H16B119.7
C11A—C16A—H16A119.7C11B—C16B—H16B119.7
O14A—N14A—O15A123.88 (14)O14B—N14B—O15B123.77 (14)
O14A—N14A—C14A118.03 (15)O14B—N14B—C14B117.99 (14)
O15A—N14A—C14A118.06 (13)O15B—N14B—C14B118.23 (13)
C27A—N2A—C2A117.35 (13)C27B—N2B—C2B116.21 (13)
N2A—C27A—C21A122.14 (14)N2B—C27B—C21B123.04 (14)
N2A—C27A—H27A118.9N2B—C27B—H27B118.5
C21A—C27A—H27A118.9C21B—C27B—H27B118.5
C26A—C21A—C22A119.60 (15)C26B—C21B—C22B119.39 (15)
C26A—C21A—C27A118.94 (14)C26B—C21B—C27B118.69 (14)
C22A—C21A—C27A121.45 (14)C22B—C21B—C27B121.89 (14)
C23A—C22A—C21A120.84 (15)C23B—C22B—C21B120.57 (14)
C23A—C22A—H22A119.6C23B—C22B—H22B119.7
C21A—C22A—H22A119.6C21B—C22B—H22B119.7
C22A—C23A—C24A117.80 (15)C22B—C23B—C24B118.59 (14)
C22A—C23A—H23A121.1C22B—C23B—H23B120.7
C24A—C23A—H23A121.1C24B—C23B—H23B120.7
C25A—C24A—C23A122.75 (15)C25B—C24B—C23B122.24 (15)
C25A—C24A—N24A118.38 (15)C25B—C24B—N24B118.55 (14)
C23A—C24A—N24A118.84 (15)C23B—C24B—N24B119.15 (14)
C24A—C25A—C26A118.82 (15)C24B—C25B—C26B118.29 (15)
C24A—C25A—H25A120.6C24B—C25B—H25B120.9
C26A—C25A—H25A120.6C26B—C25B—H25B120.9
C25A—C26A—C21A120.16 (15)C25B—C26B—C21B120.82 (15)
C25A—C26A—H26A119.9C25B—C26B—H26B119.6
C21A—C26A—H26A119.9C21B—C26B—H26B119.6
O25A—N24A—O24A123.77 (15)O25B—N24B—O24B123.58 (14)
O25A—N24A—C24A118.34 (15)O25B—N24B—C24B118.04 (14)
O24A—N24A—C24A117.88 (15)O24B—N24B—C24B118.35 (13)
N1A—C1A—C2A—N2A63.63 (15)N1B—C1B—C2B—N2B64.28 (15)
C6A—C1A—C2A—N2A175.25 (12)C6B—C1B—C2B—N2B175.74 (12)
N1A—C1A—C2A—C3A176.59 (11)N1B—C1B—C2B—C3B174.69 (12)
C6A—C1A—C2A—C3A55.47 (16)C6B—C1B—C2B—C3B54.71 (16)
N2A—C2A—C3A—C4A175.57 (13)N2B—C2B—C3B—C4B174.97 (13)
C1A—C2A—C3A—C4A55.70 (17)C1B—C2B—C3B—C4B54.75 (17)
C2A—C3A—C4A—C5A56.18 (18)C2B—C3B—C4B—C5B55.73 (17)
C3A—C4A—C5A—C6A56.15 (18)C3B—C4B—C5B—C6B56.79 (17)
C4A—C5A—C6A—C1A56.65 (18)C4B—C5B—C6B—C1B57.74 (17)
N1A—C1A—C6A—C5A176.85 (13)N1B—C1B—C6B—C5B176.23 (12)
C2A—C1A—C6A—C5A56.38 (17)C2B—C1B—C6B—C5B56.45 (16)
C6A—C1A—N1A—C17A116.25 (15)C6B—C1B—N1B—C17B105.20 (15)
C2A—C1A—N1A—C17A122.19 (14)C2B—C1B—N1B—C17B134.10 (14)
C1A—N1A—C17A—C11A178.52 (13)C1B—N1B—C17B—C11B177.12 (12)
N1A—C17A—C11A—C12A179.48 (15)N1B—C17B—C11B—C12B164.89 (14)
N1A—C17A—C11A—C16A2.4 (2)N1B—C17B—C11B—C16B14.4 (2)
C16A—C11A—C12A—C13A3.5 (2)C16B—C11B—C12B—C13B1.9 (2)
C17A—C11A—C12A—C13A174.65 (15)C17B—C11B—C12B—C13B177.44 (13)
C11A—C12A—C13A—C14A0.6 (3)C11B—C12B—C13B—C14B2.0 (2)
C12A—C13A—C14A—C15A3.0 (3)C12B—C13B—C14B—C15B0.4 (2)
C12A—C13A—C14A—N14A174.85 (14)C12B—C13B—C14B—N14B179.33 (13)
C13A—C14A—C15A—C16A3.7 (2)C13B—C14B—C15B—C16B1.3 (2)
N14A—C14A—C15A—C16A174.19 (13)N14B—C14B—C15B—C16B177.66 (13)
C14A—C15A—C16A—C11A0.7 (2)C14B—C15B—C16B—C11B1.4 (2)
C12A—C11A—C16A—C15A2.9 (2)C12B—C11B—C16B—C15B0.2 (2)
C17A—C11A—C16A—C15A175.25 (14)C17B—C11B—C16B—C15B179.14 (13)
C13A—C14A—N14A—O14A8.0 (2)C13B—C14B—N14B—O14B15.7 (2)
C15A—C14A—N14A—O14A170.00 (15)C15B—C14B—N14B—O14B163.32 (14)
C13A—C14A—N14A—O15A173.98 (15)C13B—C14B—N14B—O15B165.66 (14)
C15A—C14A—N14A—O15A8.1 (2)C15B—C14B—N14B—O15B15.3 (2)
C3A—C2A—N2A—C27A108.18 (15)C3B—C2B—N2B—C27B124.46 (15)
C1A—C2A—N2A—C27A131.08 (14)C1B—C2B—N2B—C27B113.68 (15)
C2A—N2A—C27A—C21A177.00 (13)C2B—N2B—C27B—C21B179.59 (13)
N2A—C27A—C21A—C26A167.26 (14)N2B—C27B—C21B—C26B175.66 (15)
N2A—C27A—C21A—C22A11.7 (2)N2B—C27B—C21B—C22B2.2 (2)
C26A—C21A—C22A—C23A0.6 (2)C26B—C21B—C22B—C23B1.5 (2)
C27A—C21A—C22A—C23A178.36 (14)C27B—C21B—C22B—C23B176.31 (14)
C21A—C22A—C23A—C24A1.1 (2)C21B—C22B—C23B—C24B1.3 (2)
C22A—C23A—C24A—C25A1.7 (2)C22B—C23B—C24B—C25B2.8 (2)
C22A—C23A—C24A—N24A176.62 (14)C22B—C23B—C24B—N24B174.36 (13)
C23A—C24A—C25A—C26A0.6 (2)C23B—C24B—C25B—C26B1.3 (2)
N24A—C24A—C25A—C26A177.78 (13)N24B—C24B—C25B—C26B175.88 (14)
C24A—C25A—C26A—C21A1.2 (2)C24B—C25B—C26B—C21B1.7 (2)
C22A—C21A—C26A—C25A1.8 (2)C22B—C21B—C26B—C25B3.1 (2)
C27A—C21A—C26A—C25A177.21 (13)C27B—C21B—C26B—C25B174.83 (14)
C25A—C24A—N24A—O25A2.8 (2)C25B—C24B—N24B—O25B10.2 (2)
C23A—C24A—N24A—O25A175.67 (15)C23B—C24B—N24B—O25B167.06 (14)
C25A—C24A—N24A—O24A178.04 (15)C25B—C24B—N24B—O24B171.61 (15)
C23A—C24A—N24A—O24A3.5 (2)C23B—C24B—N24B—O24B11.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22A—H22A···O15B0.952.393.280 (2)157
C25A—H25A···O15Ai0.952.433.144 (2)132
C13B—H13B···O24Bii0.952.523.225 (2)131
C27B—H27B···O24Aiii0.952.353.167 (2)143
C4A—H41A···Cg1iii0.992.653.596 (2)159
C5B—H51B···Cg2iii0.992.563.515 (2)161
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+1; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC20H20N4O4
Mr380.40
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)22.4197 (5), 8.9687 (2), 21.2076 (4)
β (°) 117.7179 (11)
V3)3774.99 (14)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.40 × 0.40 × 0.20
Data collection
DiffractometerBruker Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.968, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
43594, 8633, 6275
Rint0.043
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.129, 1.06
No. of reflections8633
No. of parameters505
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.29

Computer programs: COLLECT (Hooft, 1999; Nonius, 1997), 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 torsion angles (º) top
C2A—C1A—N1A—C17A122.19 (14)C2B—C1B—N1B—C17B134.10 (14)
C1A—N1A—C17A—C11A178.52 (13)C1B—N1B—C17B—C11B177.12 (12)
N1A—C17A—C11A—C12A179.48 (15)N1B—C17B—C11B—C12B164.89 (14)
C13A—C14A—N14A—O14A8.0 (2)C13B—C14B—N14B—O14B15.7 (2)
C1A—C2A—N2A—C27A131.08 (14)C1B—C2B—N2B—C27B113.68 (15)
C2A—N2A—C27A—C21A177.00 (13)C2B—N2B—C27B—C21B179.59 (13)
N2A—C27A—C21A—C26A167.26 (14)N2B—C27B—C21B—C26B175.66 (15)
C23A—C24A—N24A—O24A3.5 (2)C23B—C24B—N24B—O24B11.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22A—H22A···O15B0.952.393.280 (2)157
C25A—H25A···O15Ai0.952.433.144 (2)132
C13B—H13B···O24Bii0.952.523.225 (2)131
C27B—H27B···O24Aiii0.952.353.167 (2)143
C4A—H41A···Cg1iii0.992.653.596 (2)159
C5B—H51B···Cg2iii0.992.563.515 (2)161
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+1; (iii) x, y+1, z.
 

Acknowledgements

The 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 citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
First citationGlidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. E61, o1699–o1701.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationMcArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.  Google Scholar
First citationNonius (1997). KappaCCD Server Software. Windows 3.11 Version. Nonius BV, Delft, The Netherlands.  Google Scholar
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.  Google Scholar
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2003). SADABS. Version 2.10. 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

© 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.

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds