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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2101
https://doi.org/10.1107/S1600536812026025

Phenazinium methyl sulfate

Nai-Qiang Zhang,a Ping Li,b Jian Dongb and Hong-Yu Chenb*

aSchool of Basic Medical Sciences, TaiShan Medical University, Tai'an 271016, People's Republic of China, and bFaculty of Chemistry and Chemical Engineering, TaiShan Medical University, Tai'an 271016, People's Republic of China
*Correspondence e-mail: Binboll@126.com

(Received 23 May 2012; accepted 8 June 2012; online 13 June 2012)

The title salt, C12H9N2+·CH3O4S−, contains an almost planar phenazinium cation [largest deviation from the least-squares plane = 0.040 (3) Å] and a methyl sulfate anion. The sulfate moiety of the latter is disordered over two sets of sites in a 0.853 (5):0.147 (5) ratio. In the crystal, the cations and anions are arranged alternately in layers parallel to (010). The cations pack along [100] with a tilt angle of 28.96 (4)° between this axis and the mean plane and are linked through inter­planar π–π inter­actions [shortest inter­planar distance = 3.421 (4) Å]. N—H⋯O hydrogen-bonding between the cations and anions is also observed.

Related literature

For background to the use of phenazine in crystal engineering, see: Laursen & Nielsen (2004[Laursen, J. B. & Nielsen, J. (2004). Chem. Rev. 104, 1663-1685.]). For a related structure, see: Meszko et al. (2002[Meszko, J., Sikorski, A., Huta, O. M., Konitz, A. & Błażejowski, J. (2002). Acta Cryst. C58, o669-o671.]).

[Scheme 1]

Experimental

Crystal data

  • C12H9N2+·CH3O4S−

  • Mr = 292.31

  • Triclinic, [P \overline 1]

  • a = 5.818 (5) Å

  • b = 9.667 (5) Å

  • c = 11.460 (5) Å

  • α = 95.241 (5)°

  • β = 90.336 (5)°

  • γ = 93.691 (5)°

  • V = 640.5 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 293 K

  • 0.18 × 0.15 × 0.12 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.951, Tmax = 0.965

  • 3642 measured reflections

  • 2572 independent reflections

  • 2266 reflections with I > 2σ(I)

  • Rint = 0.127
Refinement

  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.185

  • S = 1.07

  • 2572 reflections

  • 191 parameters

  • H-atom parameters constrained

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.72 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H101⋯O2i 0.86 1.82 2.647 (5) 161
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339-340.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812026025/wm2637sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026025/wm2637Isup2.hkl

checkCIF report


Comment top

In the past decade, phenazines have been widely used as a template in crystal engineering for its two equivalent strong proton acceptors (sp2 N atoms) and potential weak C—H donor functions, where the aromatic system can act as a good π-donor. Accordingly, phenazine has been employed in the design of charge-transfer complexes and hydrogen bonded assemblies (Laursen et al., 2004). Here, we report the crystal structure of an 1:1 complex of phenazine with methyl sulfate.

The asymmetric unit of the title salt, [C12H9N2]+ [CH3O4S]-, contains a phenazinium cation and a methyl sulfate anion (Fig. 1), which is located around the inversion centre. The phenazinium cations show an almost planar configuration, where the largest deviation from the least-square-plane of phenazine is 0.040 (3)Å for C3. The methyl sulfate anions are disordered over two positions in a ratio of 0.853 (5):0.147 (5). The distribution of S—O bond lengths in the methyl sulfate anion is similar to that in the crystal structure of 10-methylacridinium methyl sulfate (Meszko et al., 2002). The S—O bond lengths associated with the methyl group [1.614 (2) Å for the major and 1.486 (18) for the minor part] are longer than the other S—O bonds (1.421 (3) Å, 1.448 (2) Å and 1.423 (2) Å (major part); 1.516 (16) Å (minor part)).

The cations pack along [100] with a tilt angle between the phenazinium plane and the a axis being 28.96 (4)°. The shortest plane-to-plane π—π interactions are 3.421 (4) Å. The phenazinium cations and the methyl sulfate anions are alternately arranged parallel to (010) (Fig. 2). Except for Coulombic interactions, there are classical hydrogen bonding interactions between the phenazinium cations and methyl sulfate anions (Table 1), which also play an important role in the stabilisation of the title structure.

Related literature top

For background to the use of phenazine in crystal engineering, see: Laursen & Nielsen (2004). For a related structure, see: Meszko et al. (2002).

Experimental top

To a solution containing phenzine (1.0 g, 0.0056 mmol) in n-butyl acetate (20 mL) was added dimethyl sulfate (5.4 mL, 0.057 mmol). The resulting mixture was continuously stired at 373 K for 1 h, then the orange reaction solution was cooled to 283 K. The precipitated yellow solid were collected and recrystallized in ethanol.

Refinement top

All H atoms were geometrically fixed and allowed to ride on their attached atoms, whit C—H = 0.93 Å and Uiso(H)= 1.2Ueq(C) for all phenzine H atoms, and C—H = 0.96 Å and Uiso(H)= 1.5Ueq(C) for the methyl group. The proton attached to the phenazine N atom was also geometrically fixed, with N—H = 0.86Å and Uiso(H)= 1.2Ueq(N). The sulfate part of the anion was modelled as disordered over two sets of sites in a 0.853 (5):0.147 (5) ratio; O atoms of the minor component were refined with isotropic displacement parameters.

Structure description top

In the past decade, phenazines have been widely used as a template in crystal engineering for its two equivalent strong proton acceptors (sp2 N atoms) and potential weak C—H donor functions, where the aromatic system can act as a good π-donor. Accordingly, phenazine has been employed in the design of charge-transfer complexes and hydrogen bonded assemblies (Laursen et al., 2004). Here, we report the crystal structure of an 1:1 complex of phenazine with methyl sulfate.

The asymmetric unit of the title salt, [C12H9N2]+ [CH3O4S]-, contains a phenazinium cation and a methyl sulfate anion (Fig. 1), which is located around the inversion centre. The phenazinium cations show an almost planar configuration, where the largest deviation from the least-square-plane of phenazine is 0.040 (3)Å for C3. The methyl sulfate anions are disordered over two positions in a ratio of 0.853 (5):0.147 (5). The distribution of S—O bond lengths in the methyl sulfate anion is similar to that in the crystal structure of 10-methylacridinium methyl sulfate (Meszko et al., 2002). The S—O bond lengths associated with the methyl group [1.614 (2) Å for the major and 1.486 (18) for the minor part] are longer than the other S—O bonds (1.421 (3) Å, 1.448 (2) Å and 1.423 (2) Å (major part); 1.516 (16) Å (minor part)).

The cations pack along [100] with a tilt angle between the phenazinium plane and the a axis being 28.96 (4)°. The shortest plane-to-plane π—π interactions are 3.421 (4) Å. The phenazinium cations and the methyl sulfate anions are alternately arranged parallel to (010) (Fig. 2). Except for Coulombic interactions, there are classical hydrogen bonding interactions between the phenazinium cations and methyl sulfate anions (Table 1), which also play an important role in the stabilisation of the title structure.

For background to the use of phenazine in crystal engineering, see: Laursen & Nielsen (2004). For a related structure, see: Meszko et al. (2002).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with displacement ellipsoids at the 50% probability level. The disorder of the anion is shown.
[Figure 2] Fig. 2. A packing diagram of the title structure viewed approximately along [100]. Hydrogen bonding interactions are shown with dashed lines.
Phenazinium methyl sulfate top
Crystal data top
C12H9N2+·CH3O4S−Z = 2
Mr = 292.31F(000) = 304
Triclinic, P1Dx = 1.516 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 5.818 (5) ÅCell parameters from 4012 reflections
b = 9.667 (5) Åθ = 0.4–14.1°
c = 11.460 (5) ŵ = 0.27 mm−1
α = 95.241 (5)°T = 293 K
β = 90.336 (5)°Block, yellow
γ = 93.691 (5)°0.18 × 0.15 × 0.12 mm
V = 640.5 (7) Å3
Data collection top
Bruker APEXII CCD
diffractometer		2572 independent reflections
Radiation source: fine-focus sealed tube2266 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.127
φ– and ω– scansθmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −7→6
Tmin = 0.951, Tmax = 0.965k = −12→11
3642 measured reflectionsl = −14→12
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1118P)2 + 0.2488P]
where P = (Fo2 + 2Fc2)/3
2572 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.54 e Å−3
0 restraintsΔρmin = −0.72 e Å−3
Crystal data top
C12H9N2+·CH3O4S−γ = 93.691 (5)°
Mr = 292.31V = 640.5 (7) Å3
Triclinic, P1Z = 2
a = 5.818 (5) ÅMo Kα radiation
b = 9.667 (5) ŵ = 0.27 mm−1
c = 11.460 (5) ÅT = 293 K
α = 95.241 (5)°0.18 × 0.15 × 0.12 mm
β = 90.336 (5)°
Data collection top
Bruker APEXII CCD
diffractometer		2572 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		2266 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.965Rint = 0.127
3642 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.185H-atom parameters constrained
S = 1.07Δρmax = 0.54 e Å−3
2572 reflectionsΔρmin = −0.72 e Å−3
191 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.3313 (3)0.1672 (2)0.84021 (18)0.0391 (5)
H1010.21160.21320.83180.047*
N20.7148 (3)0.0191 (2)0.86741 (19)0.0432 (5)
C10.4340 (4)0.3195 (3)1.0121 (2)0.0447 (6)
H1000.30310.36861.00530.054*
C20.5880 (5)0.3558 (3)1.1006 (2)0.0512 (6)
H20.56130.43021.15500.061*
C30.7895 (5)0.2821 (3)1.1116 (2)0.0508 (6)
H30.89520.31121.17140.061*
C40.8303 (4)0.1705 (3)1.0367 (2)0.0461 (6)
H40.96020.12141.04680.055*
C50.6737 (4)0.1283 (2)0.9423 (2)0.0380 (5)
C60.4758 (4)0.2065 (2)0.9312 (2)0.0372 (5)
C70.3673 (4)0.0595 (3)0.7627 (2)0.0406 (5)
C80.2129 (5)0.0209 (3)0.6681 (2)0.0538 (7)
H80.08210.06940.65880.065*
C90.2593 (6)−0.0875 (3)0.5918 (3)0.0640 (8)
H90.1585−0.11360.52920.077*
C100.4572 (6)−0.1629 (3)0.6041 (3)0.0636 (8)
H100.4855−0.23610.54870.076*
C110.6058 (5)−0.1301 (3)0.6951 (3)0.0557 (7)
H110.7332−0.18200.70320.067*
C120.5663 (4)−0.0160 (3)0.7782 (2)0.0414 (5)
S10.88381 (9)0.37619 (6)0.71184 (5)0.0422 (3)
O1A0.8047 (4)0.5126 (3)0.7145 (2)0.0583 (8)0.853 (5)
O21.0304 (4)0.3550 (2)0.81033 (17)0.0602 (6)
O30.7187 (5)0.2637 (3)0.6816 (3)0.0894 (9)
O4A1.0400 (4)0.3553 (3)0.59643 (19)0.0545 (7)0.853 (5)
C131.2319 (5)0.4504 (4)0.5904 (3)0.0679 (9)
H13A1.18750.54290.61290.102*
H13B1.28840.44540.51170.102*
H13C1.35070.42780.64260.102*
O1B1.035 (3)0.4806 (16)0.6513 (14)0.063 (5)*0.147 (5)
O4B0.718 (3)0.4697 (18)0.7705 (17)0.069 (5)*0.147 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0301 (9)0.0466 (11)0.0416 (10)0.0090 (8)−0.0058 (8)0.0053 (8)
N20.0344 (10)0.0489 (12)0.0471 (11)0.0108 (8)−0.0026 (9)0.0032 (9)
C10.0416 (13)0.0469 (13)0.0465 (13)0.0125 (10)−0.0029 (11)0.0034 (10)
C20.0561 (15)0.0510 (14)0.0457 (14)0.0085 (12)−0.0037 (12)−0.0027 (11)
C30.0452 (14)0.0609 (16)0.0455 (13)0.0025 (12)−0.0137 (11)0.0018 (11)
C40.0337 (12)0.0571 (15)0.0487 (13)0.0088 (10)−0.0081 (11)0.0077 (11)
C50.0285 (10)0.0443 (12)0.0420 (12)0.0061 (9)−0.0010 (9)0.0063 (9)
C60.0313 (11)0.0426 (12)0.0389 (11)0.0054 (9)−0.0021 (9)0.0073 (9)
C70.0347 (11)0.0465 (13)0.0406 (12)0.0027 (9)−0.0030 (10)0.0041 (10)
C80.0491 (15)0.0617 (16)0.0497 (14)0.0034 (12)−0.0147 (12)0.0017 (12)
C90.0687 (19)0.0686 (19)0.0517 (16)0.0006 (15)−0.0150 (14)−0.0065 (14)
C100.072 (2)0.0604 (17)0.0547 (16)0.0045 (15)0.0017 (15)−0.0138 (13)
C110.0527 (15)0.0530 (15)0.0603 (16)0.0112 (12)0.0039 (13)−0.0057 (12)
C120.0346 (11)0.0471 (13)0.0424 (12)0.0040 (9)0.0013 (10)0.0029 (10)
S10.0289 (3)0.0536 (4)0.0452 (4)0.0116 (2)−0.0043 (2)0.0049 (3)
O1A0.0508 (14)0.0665 (16)0.0608 (15)0.0302 (12)−0.0018 (12)0.0050 (12)
O20.0572 (12)0.0763 (14)0.0491 (11)0.0274 (10)−0.0149 (9)0.0008 (9)
O30.0926 (19)0.0844 (18)0.0879 (18)−0.0211 (15)−0.0266 (16)0.0104 (14)
O4A0.0513 (13)0.0639 (15)0.0479 (13)0.0122 (11)0.0020 (10)−0.0033 (10)
C130.0365 (13)0.107 (3)0.0619 (17)0.0065 (15)0.0059 (13)0.0143 (17)
Geometric parameters (Å, º) top
N1—C71.333 (3)C8—H80.9300
N1—C61.347 (3)C9—C101.415 (5)
N1—H1010.8600C9—H90.9300
N2—C51.333 (3)C10—C111.353 (4)
N2—C121.340 (3)C10—H100.9300
C1—C21.355 (4)C11—C121.422 (4)
C1—C61.401 (3)C11—H110.9300
C1—H1000.9300S1—O31.421 (3)
C2—C31.421 (4)S1—O1A1.423 (2)
C2—H20.9300S1—O21.448 (2)
C3—C41.350 (4)S1—O4B1.486 (18)
C3—H30.9300S1—O1B1.516 (16)
C4—C51.424 (3)S1—O4A1.614 (2)
C4—H40.9300O4A—C131.406 (4)
C5—C61.429 (3)C13—H13A0.9600
C7—C81.412 (3)C13—H13B0.9600
C7—C121.426 (4)C13—H13C0.9600
C8—C91.345 (4)
C7—N1—C6122.4 (2)C8—C9—C10121.8 (3)
C7—N1—H101118.8C8—C9—H9119.1
C6—N1—H101118.8C10—C9—H9119.1
C5—N2—C12118.3 (2)C11—C10—C9121.1 (3)
C2—C1—C6118.8 (2)C11—C10—H10119.5
C2—C1—H100120.6C9—C10—H10119.5
C6—C1—H100120.6C10—C11—C12119.6 (3)
C1—C2—C3121.2 (2)C10—C11—H11120.2
C1—C2—H2119.4C12—C11—H11120.2
C3—C2—H2119.4N2—C12—C11120.2 (2)
C4—C3—C2121.2 (2)N2—C12—C7121.7 (2)
C4—C3—H3119.4C11—C12—C7118.1 (2)
C2—C3—H3119.4O3—S1—O1A116.76 (18)
C3—C4—C5119.7 (2)O3—S1—O2113.70 (16)
C3—C4—H4120.1O1A—S1—O2114.03 (13)
C5—C4—H4120.1O3—S1—O4B95.5 (7)
N2—C5—C4119.9 (2)O1A—S1—O4B37.2 (7)
N2—C5—C6122.1 (2)O2—S1—O4B100.4 (7)
C4—C5—C6118.0 (2)O3—S1—O1B138.7 (6)
N1—C6—C1121.5 (2)O1A—S1—O1B64.2 (6)
N1—C6—C5117.4 (2)O2—S1—O1B100.5 (6)
C1—C6—C5121.1 (2)O4B—S1—O1B100.4 (10)
N1—C7—C8121.1 (2)O3—S1—O4A97.18 (17)
N1—C7—C12118.1 (2)O1A—S1—O4A106.51 (15)
C8—C7—C12120.9 (2)O2—S1—O4A106.33 (13)
C9—C8—C7118.5 (3)O4B—S1—O4A142.5 (8)
C9—C8—H8120.7O1B—S1—O4A49.6 (6)
C7—C8—H8120.7C13—O4A—S1116.1 (2)
C6—C1—C2—C30.4 (4)C12—C7—C8—C9−0.9 (4)
C1—C2—C3—C4−2.3 (5)C7—C8—C9—C100.0 (5)
C2—C3—C4—C52.3 (4)C8—C9—C10—C111.3 (6)
C12—N2—C5—C4−178.6 (2)C9—C10—C11—C12−1.6 (5)
C12—N2—C5—C61.0 (4)C5—N2—C12—C11178.9 (2)
C3—C4—C5—N2179.2 (2)C5—N2—C12—C7−0.5 (4)
C3—C4—C5—C6−0.5 (4)C10—C11—C12—N2−178.7 (3)
C7—N1—C6—C1−179.6 (2)C10—C11—C12—C70.7 (4)
C7—N1—C6—C50.3 (4)N1—C7—C12—N2−0.1 (4)
C2—C1—C6—N1−178.8 (2)C8—C7—C12—N2180.0 (2)
C2—C1—C6—C51.4 (4)N1—C7—C12—C11−179.5 (2)
N2—C5—C6—N1−0.9 (4)C8—C7—C12—C110.6 (4)
C4—C5—C6—N1178.8 (2)O3—S1—O4A—C13179.8 (2)
N2—C5—C6—C1178.9 (2)O1A—S1—O4A—C1359.1 (3)
C4—C5—C6—C1−1.4 (4)O2—S1—O4A—C13−62.9 (3)
C6—N1—C7—C8−179.9 (2)O4B—S1—O4A—C1370.9 (11)
C6—N1—C7—C120.2 (4)O1B—S1—O4A—C1327.2 (8)
N1—C7—C8—C9179.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H101···O2i0.861.822.647 (5)161
Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC12H9N2+·CH3O4S−
Mr292.31
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)5.818 (5), 9.667 (5), 11.460 (5)
α, β, γ (°)95.241 (5), 90.336 (5), 93.691 (5)
V (Å3)640.5 (7)
Z2
Radiation typeMo Kα
µ (mm−1)0.27
Crystal size (mm)0.18 × 0.15 × 0.12
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.951, 0.965
No. of measured, independent and
observed [I > 2σ(I)] reflections		3642, 2572, 2266
Rint0.127
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.185, 1.07
No. of reflections2572
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.54, −0.72

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H101···O2i0.861.8182.647 (5)161.37
Symmetry code: (i) x−1, y, z.
 

Acknowledgements

This work was supported by the Shandong College research program (J11LB15) and the Young and Middle-aged Scientist Research Awards Foundation of Shandong Province (BS2010CL045).

References

First citationAltomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339–340.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationBruker (2005). APEX, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationLaursen, J. B. & Nielsen, J. (2004). Chem. Rev. 104, 1663–1685.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationMeszko, J., Sikorski, A., Huta, O. M., Konitz, A. & Błażejowski, J. (2002). Acta Cryst. C58, o669–o671.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2101
https://doi.org/10.1107/S1600536812026025
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