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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

2-(2-Pyridyl)pyridinium perchlorate, redetermined at 120 K: complex hydrogen-bonded sheets

aSchool of Chemistry, Bharathidasan University, Tiruchirappalli, Tamil Nadu 620 024, India, bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 9 June 2005; accepted 13 June 2005; online 9 July 2005)

In the title compound, C10H9N2+·ClO4, the ions are linked into complex sheets by the combination of one N—H⋯O and four independent C—H⋯O hydrogen bonds.

Comment

The structure of the title compound, (I)[link], was determined many years ago (Lipkowski et al., 1976[Lipkowski, J., Sgarabotto, P. & Andreetti, G. D. (1976). Cryst. Struct. Commun. 5, 931-934.]); using diffraction data collected at ambient temperature, the structure was refined only to R = 0.072. We have now redetermined this structure using diffraction data collected at 120 K and report here a more precise determination, together with the inter­esting supramolecular structure of this compound. The space group and unit-cell dimensions confirm that the previous study and the present work involve the same phase.

[Scheme 1]

The title compound (Fig. 1[link]) is a salt, and in the selected asymmetric unit, the two ions are linked by an N—H⋯O hydrogen bond. In the cation, the dihedral angle between the two ring planes is 14.96 (15)°, similar to the value of 16.6° reported previously for the ambient-temperature structure (Lipkowski et al., 1976[Lipkowski, J., Sgarabotto, P. & Andreetti, G. D. (1976). Cryst. Struct. Commun. 5, 931-934.]). In addition, there is a significant difference in the C—N—C angles at the protonated atom N11 and the unprotonated atom N21 (Table 1[link]). In the anion, the Cl—O distance involving atom O1 is somewhat longer than the other Cl—O distances, possibly reflecting some modest localization of the negative charge.

In addition to the N—H⋯O hydrogen bond, involving the more negative atom O1 as the acceptor, there are a number of independent C—H⋯O hydrogen bonds (Table 2[link]). Although these all have fairly long H⋯O distances, they all appear to have some structural significance, including the effective tethering of the perchlorate anion, for which the anisotropic displacement parameters give no indication of significant libration, far less of the type of disorder for which this anion is notorious. Hence, we conclude that these inter­actions are significant. All of the hydrogen bonds involve donors in the protonated pyridinium ring, leading to more acidic X—H bonds (X = C or N), and all four O atoms of the anion act as acceptors, so precluding any significant librational motion for the anion.

The C—H⋯O hydrogen bond involving atom C16 as the donor reinforces the N—H⋯O hydrogen bond in linking together the two independent ions, so forming an R22(7) motif, and the combination of this and the inter­action having atom C13 as the donor then generates by translation a C22(8)C22(9)[R22(7)] chain of rings running parallel to the [10[\overline{1}]] direction (Fig. 2[link]). The two hydrogen bonds having atoms C14 and C15 as the donors act co-operatively to form a zigzag chain of edge-fused rings running parallel to the [20[\overline{1}]] direction and generated by the c-glide plane at y = 0 (Fig. 3[link]). The combination of the [10[\overline{1}]] and [20[\overline{1}]] chains then generates a complex (010) sheet.

[Figure 1]
Figure 1
The independent components of compound (I)[link], showing the atom-labelling scheme and the N—H⋯O hydrogen bond (dashed line). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2]
Figure 2
Part of the crystal structure of (I)[link], showing the formation of a hydrogen-bonded chain of rings along [10[\overline{1}]]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x − 1, y, 1 + z) and (1 + x, y, z − 1), respectively.
[Figure 3]
Figure 3
Part of the crystal structure of (I)[link], showing the formation of a hydrogen-bonded chain of rings along [20[\overline{1}]]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x − 1, −y, [{1\over 2}] + z) and (1 + x, −y, z − [{1\over 2}]), respectively.

Experimental

2,2′-Bipyridine (3.2 mmol) was dissolved in ethanol (25 ml) and perchloric acid (3.2 mmol) was then added dropwise. The reaction mixture was warmed in a water bath for 15 min and colourless crystals of (I)[link] separated out on cooling (m.p. 441 K).

Crystal data
  • C10H9N2+·ClO4

  • Mr = 256.64

  • Monoclinic, P c

  • a = 5.958 (4) Å

  • b = 12.854 (4) Å

  • c = 7.060 (11) Å

  • β = 100.26 (7)°

  • V = 532.0 (9) Å3

  • Z = 2

  • Dx = 1.602 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 2313 reflections

  • θ = 3.2–27.5°

  • μ = 0.36 mm−1

  • T = 120 (2) K

  • Plate, colourless

  • 0.18 × 0.12 × 0.02 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 = 0.954, Tmax = 0.993

  • 6904 measured reflections

  • 2313 independent reflections

  • 2035 reflections with I > 2σ(I)

  • Rint = 0.046

  • θmax = 27.5°

  • h = −7 → 7

  • k = −16 → 16

  • l = −9 → 9

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.115

  • S = 1.07

  • 2313 reflections

  • 155 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0712P)2 + 0.011P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.46 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 1086 Friedel pairs

  • Flack parameter: 0.03 (16)

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

Cl1—O1 1.452 (3)
Cl1—O2 1.433 (2)
Cl1—O3 1.439 (2)
Cl1—O4 1.438 (3)
C12—N11—C16 123.3 (3)
C22—N21—C26 117.0 (2)
N11—C12—C22—N21 −14.6 (4)
N11—C12—C22—C23 166.0 (3)
C13—C12—C22—N21 164.1 (3)
C13—C12—C22—C23 −15.3 (4)

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

D—H⋯A D—H H⋯A DA D—H⋯A
N11—H11⋯O1 0.88 2.11 2.902 (6) 150
C13—H13⋯O4i 0.95 2.51 3.328 (7) 144
C14—H14⋯O3ii 0.95 2.57 3.375 (7) 142
C15—H15⋯O2ii 0.95 2.57 3.365 (6) 141
C16—H16⋯O3 0.95 2.52 3.289 (6) 139
Symmetry codes: (i) x-1, y, z+1; (ii) [x-1, -y, z+{\script{1\over 2}}].

The systematic absences permitted Pc and P2/c as possible space groups; Pc was selected and confirmed by the subsequent analysis. All H atoms were located in difference maps and then treated as riding atoms, with C—H distances of 0.95 Å and N—H distances of 0.88 Å, and with Uiso(H) = 1.2Ueq(C,N). The correct orientation of the structure with respect to the polar-axis directions (Jones, 1986[Jones, P. G. (1986). Acta Cryst. A42, 57.]) was determined by means of 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 structure of the title compound, (I), was determined many years ago (Lipkowski et al., 1976); using diffraction data collected at ambient temperature, the structure was refined only to R = 0.072. We have now redetermined this structure using diffraction data collected at 120 K, and we report here a more precise determination, together with the interesting supramolecular structure of this compound. The space group and unit-cell dimensions confirm that the previous study and the present work involve the same phase.

The title compound (Fig. 1) is a salt, and in the selected asymmetric unit, the two ions are linked by an N—H···O hydrogen bond. In the cation, the dihedral angle between the two ring planes is 14.96 (15)°, similar to the 16.6° reported earlier for the ambient-temperature structure (Lipkowski et al., 1976). In addition, there is a significant difference in the C—N—C angles at the protonated atom N11 and the unprotonated atom N21 (Table 1). In the anion, the Cl—O distance involving atom O1 is somewhat longer than the other Cl—O distances, possibly reflecting some modest localization of the negative charge.

In addition to the N—H···O hydrogen bond, involving the more negative atom O1 as the acceptor, there are a number of independent C—H···O hydrogen bonds (Table 2). Although these all have fairly long H···O distances, they all appear to have some structural significance, including the effective tethering of the perchlorate anion, for which the anisotropic displacement parameters give no indication of significant libration, far less of the type of disorder for which this anion is notorious. Hence we conclude that these interactions are significant. All of the hydrogen bonds involve donors in the protonated pyridinium ring, leading to more acidic X—H bonds (X = C or N), and all four O atoms of the anion act as acceptors, so precluding any significant librational motion for the anion.

The C—H···O hydrogen bond involving atom C16 as the donor reinforces the N—H···O hydrogen bond in linking together the two independent ions, so forming an R22(7) motif, and the combination of this and the interaction having atom C13 as the donor then generates by translation a C22(8)C22(9)[R22(7)] chain of rings running parallel to the [101] direction (Fig. 2). The two hydrogen bonds having atoms C14 and C15 as the donors act cooperatively to form a zigzag chain of edge-fused rings running parallel to the [201] direction and generated by the c-glide plane at y = 0 (Fig. 3). The combination of the [101] and [201] chains then generates a complex (010) sheet.

Experimental top

2,2'-Bipyridine (3.2 mmol) was dissolved in ethanol (Volume?) and perchloric acid (3.2 mmol) was then added dropwise. The reaction mixture was warmed in a water bath for 15 min and colourless crystals of (I) suitable for single-crystal X-ray diffraction separated out on cooling (m.p. 441 K).

Refinement top

The systematic absences permitted Pc and P2/c as possible space groups. Pc was selected and confirmed by the subsequent analysis. All H atoms were located in difference maps and then treated as riding atoms, with C—H distances of 0.95 Å and N—H distances of 0.88 Å, and with Uiso(H) = 1.2Ueq(C,N). The correct orientation of the structure with respect to the polar axis directions (Jones, 1986) was determined by means of the Flack parameter (Flack, 1983).

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 independent components of compound (I), showing the atom-labelling scheme and the N—H···O hydrogen bond (dashed line). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain of rings along [101]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x − 1, y, 1 + z) and (1 + x, y, z − 1), respectively.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded chains of rings along [201]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x − 1, −y, 1/2 + z) and (1 + x, −y, z − 1/2), respectively.
2-(2-Pyridyl)pyridinium perchlorate top
Crystal data top
C10H9N2+·ClO4F(000) = 264
Mr = 256.64Dx = 1.602 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 2313 reflections
a = 5.958 (4) Åθ = 3.2–27.5°
b = 12.854 (4) ŵ = 0.36 mm1
c = 7.060 (11) ÅT = 120 K
β = 100.26 (7)°Plate, colourless
V = 532.0 (9) Å30.18 × 0.12 × 0.02 mm
Z = 2
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
2313 independent reflections
Radiation source: Bruker-Nonius FR91 rotating anode2035 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.2°
ϕ and ω scansh = 77
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1616
Tmin = 0.954, Tmax = 0.993l = 99
6904 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)] = 0.044H-atom parameters constrained
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0712P)2 + 0.011P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2313 reflectionsΔρmax = 0.46 e Å3
155 parametersΔρmin = 0.46 e Å3
2 restraintsAbsolute structure: Flack (1983), with 1086 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (16)
Crystal data top
C10H9N2+·ClO4V = 532.0 (9) Å3
Mr = 256.64Z = 2
Monoclinic, PcMo Kα radiation
a = 5.958 (4) ŵ = 0.36 mm1
b = 12.854 (4) ÅT = 120 K
c = 7.060 (11) Å0.18 × 0.12 × 0.02 mm
β = 100.26 (7)°
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
2313 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2035 reflections with I > 2σ(I)
Tmin = 0.954, Tmax = 0.993Rint = 0.046
6904 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.115Δρmax = 0.46 e Å3
S = 1.07Δρmin = 0.46 e Å3
2313 reflectionsAbsolute structure: Flack (1983), with 1086 Friedel pairs
155 parametersAbsolute structure parameter: 0.03 (16)
2 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.78153 (11)0.18772 (5)0.12569 (11)0.02248 (19)
O10.7292 (4)0.25897 (17)0.2714 (3)0.0264 (5)
O21.0236 (4)0.18298 (16)0.1357 (3)0.0288 (5)
O30.6951 (4)0.08604 (18)0.1587 (4)0.0432 (7)
O40.6765 (4)0.2262 (2)0.0603 (3)0.0397 (6)
N110.3950 (4)0.21493 (19)0.5136 (4)0.0205 (5)
N210.4404 (4)0.42048 (19)0.5365 (4)0.0221 (6)
C120.2347 (5)0.2674 (2)0.5864 (4)0.0207 (6)
C130.0777 (5)0.2114 (3)0.6677 (5)0.0244 (7)
C140.0897 (5)0.1034 (3)0.6715 (5)0.0256 (7)
C150.2574 (6)0.0523 (2)0.5932 (5)0.0277 (7)
C160.4097 (5)0.1101 (2)0.5145 (4)0.0240 (7)
C220.2440 (5)0.3824 (2)0.5763 (4)0.0200 (6)
C230.0631 (5)0.4445 (2)0.6077 (5)0.0231 (6)
C240.0889 (5)0.5522 (2)0.6041 (5)0.0247 (6)
C250.2908 (5)0.5928 (2)0.5643 (4)0.0237 (6)
C260.4596 (5)0.5242 (2)0.5293 (5)0.0241 (6)
H110.49540.25070.46270.025*
H130.03730.24640.72050.029*
H140.01700.06440.72770.031*
H150.26600.02150.59450.033*
H160.52570.07670.46040.029*
H230.07490.41430.63110.028*
H240.02980.59690.62840.030*
H250.31360.66590.56090.028*
H260.59610.55250.49870.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0211 (3)0.0219 (3)0.0249 (4)0.0002 (3)0.0053 (2)0.0006 (3)
O10.0290 (11)0.0263 (12)0.0264 (12)0.0023 (8)0.0116 (8)0.0028 (9)
O20.0180 (11)0.0313 (13)0.0376 (14)0.0023 (8)0.0066 (10)0.0009 (9)
O30.0449 (15)0.0218 (13)0.068 (2)0.0139 (11)0.0248 (14)0.0085 (12)
O40.0348 (14)0.0613 (17)0.0212 (13)0.0141 (11)0.0005 (10)0.0028 (11)
N110.0211 (12)0.0219 (12)0.0187 (13)0.0006 (10)0.0043 (10)0.0021 (10)
N210.0209 (12)0.0234 (13)0.0230 (14)0.0002 (10)0.0069 (10)0.0016 (10)
C120.0166 (14)0.0248 (15)0.0202 (16)0.0015 (11)0.0019 (11)0.0005 (12)
C130.0209 (15)0.0303 (16)0.0224 (17)0.0003 (12)0.0045 (12)0.0037 (13)
C140.0237 (15)0.0268 (16)0.0263 (17)0.0043 (12)0.0042 (12)0.0077 (13)
C150.0309 (17)0.0239 (15)0.0260 (19)0.0025 (13)0.0010 (14)0.0017 (13)
C160.0298 (16)0.0209 (15)0.0204 (16)0.0026 (11)0.0018 (12)0.0001 (12)
C220.0155 (13)0.0259 (15)0.0180 (16)0.0012 (10)0.0010 (11)0.0007 (11)
C230.0202 (15)0.0233 (15)0.0257 (16)0.0016 (11)0.0043 (12)0.0022 (12)
C240.0245 (15)0.0239 (16)0.0244 (16)0.0011 (12)0.0005 (12)0.0022 (13)
C250.0233 (15)0.0220 (15)0.0233 (16)0.0003 (11)0.0026 (13)0.0023 (11)
C260.0200 (13)0.0283 (16)0.0235 (15)0.0041 (12)0.0028 (11)0.0014 (12)
Geometric parameters (Å, º) top
N11—C121.344 (4)N21—C221.344 (4)
N11—C161.350 (4)C22—C231.391 (4)
N11—H110.88C23—C241.393 (4)
C12—C131.383 (4)C23—H230.95
C12—C221.481 (4)C24—C251.386 (4)
C13—C141.390 (4)C24—H240.95
C13—H130.95C25—C261.392 (4)
C14—C151.390 (5)C25—H250.95
C14—H140.95C26—H260.95
C15—C161.365 (5)Cl1—O11.452 (3)
C15—H150.95Cl1—O21.433 (2)
C16—H160.95Cl1—O31.439 (2)
N21—C261.340 (4)Cl1—O41.438 (3)
C12—N11—C16123.3 (3)N21—C22—C12114.5 (2)
C12—N11—H11118.4C23—C22—C12121.9 (2)
C16—N11—H11118.4C22—C23—C24118.5 (3)
N11—C12—C13118.5 (3)C22—C23—H23120.8
N11—C12—C22116.6 (2)C24—C23—H23120.8
C13—C12—C22125.0 (3)C25—C24—C23118.7 (3)
C12—C13—C14119.5 (3)C25—C24—H24120.6
C12—C13—H13120.3C23—C24—H24120.6
C14—C13—H13120.3C24—C25—C26118.5 (3)
C13—C14—C15120.2 (3)C24—C25—H25120.7
C13—C14—H14119.9C26—C25—H25120.7
C15—C14—H14119.9N21—C26—C25123.7 (3)
C16—C15—C14118.8 (3)N21—C26—H26118.2
C16—C15—H15120.6C25—C26—H26118.2
C14—C15—H15120.6O2—Cl1—O4109.28 (16)
N11—C16—C15119.9 (3)O2—Cl1—O3109.86 (15)
N11—C16—H16120.1O4—Cl1—O3110.53 (18)
C15—C16—H16120.1O2—Cl1—O1109.47 (15)
C22—N21—C26117.0 (2)O4—Cl1—O1108.43 (16)
N21—C22—C23123.5 (3)O3—Cl1—O1109.26 (16)
C16—N11—C12—C130.5 (4)N11—C12—C22—N2114.6 (4)
C16—N11—C12—C22179.3 (2)N11—C12—C22—C23166.0 (3)
N11—C12—C13—C140.1 (4)C13—C12—C22—N21164.1 (3)
C22—C12—C13—C14178.8 (3)C13—C12—C22—C2315.3 (4)
C12—C13—C14—C150.4 (5)N21—C22—C23—C242.2 (5)
C13—C14—C15—C160.5 (5)C12—C22—C23—C24177.2 (3)
C12—N11—C16—C150.4 (5)C22—C23—C24—C251.7 (5)
C14—C15—C16—N110.1 (4)C23—C24—C25—C260.1 (4)
C26—N21—C22—C230.7 (4)C22—N21—C26—C251.3 (4)
C26—N21—C22—C12178.7 (3)C24—C25—C26—N211.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O10.882.112.902 (6)150
C13—H13···O4i0.952.513.328 (7)144
C14—H14···O3ii0.952.573.375 (7)142
C15—H15···O2ii0.952.573.365 (6)141
C16—H16···O30.952.523.289 (6)139
Symmetry codes: (i) x1, y, z+1; (ii) x1, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC10H9N2+·ClO4
Mr256.64
Crystal system, space groupMonoclinic, Pc
Temperature (K)120
a, b, c (Å)5.958 (4), 12.854 (4), 7.060 (11)
β (°) 100.26 (7)
V3)532.0 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.36
Crystal size (mm)0.18 × 0.12 × 0.02
Data collection
DiffractometerBruker Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.954, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
6904, 2313, 2035
Rint0.046
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.115, 1.07
No. of reflections2313
No. of parameters155
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.46
Absolute structureFlack (1983), with 1086 Friedel pairs
Absolute structure parameter0.03 (16)

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
Cl1—O11.452 (3)Cl1—O31.439 (2)
Cl1—O21.433 (2)Cl1—O41.438 (3)
C12—N11—C16123.3 (3)C22—N21—C26117.0 (2)
N11—C12—C22—N2114.6 (4)C13—C12—C22—N21164.1 (3)
N11—C12—C22—C23166.0 (3)C13—C12—C22—C2315.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O10.882.112.902 (6)150
C13—H13···O4i0.952.513.328 (7)144
C14—H14···O3ii0.952.573.375 (7)142
C15—H15···O2ii0.952.573.365 (6)141
C16—H16···O30.952.523.289 (6)139
Symmetry codes: (i) x1, y, z+1; (ii) x1, y, z+1/2.
 

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.

References

First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationJones, P. G. (1986). Acta Cryst. A42, 57.  CrossRef Web of Science IUCr Journals Google Scholar
First citationLipkowski, J., Sgarabotto, P. & Andreetti, G. D. (1976). Cryst. Struct. Commun. 5, 931–934.  CAS Google Scholar
First citationMcArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.  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

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