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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 10| October 2008| Pages o1965-o1966

A second monoclinic polymorph of 4-(2-hydr­­oxy-4-meth­oxy­benzyl­­idene­amino)-1,5-di­methyl-2-phenyl-1H-pyrazol-3(2H)-one

aDepartment of Chemistry, Hebei Normal College of Science and Technology, Qinhuangdao 066600, People's Republic of China
*Correspondence e-mail: zhaofu_zhu@163.com

(Received 13 September 2008; accepted 15 September 2008; online 20 September 2008)

The title compound, C19H19N3O3, prepared by condensing 4-amino­anti­pyrine and 4-meth­oxy-2-hydroxy­benzaldehyde in methanol, is the second monoclinic polymorph of this compound which crystallizes in the space group C2/c. The structure was previously reported [Wang, Zhang, Yan, Zheng & Yang (2007[Wang, L.-G., Zhang, C.-N., Yan, G.-B., Zheng, Y.-F. & Yang, M.-H. (2007). Acta Cryst. E63, o1245-o1246.]). Acta Cryst. E63, o1245–o1246] in the space group P21/c. The hydroxyl group is disordered over two positions with occupancies of 0.787 (4) and 0.213 (4). The triply substituted benzene ring and the phenyl ring form dihedral angles of 12.2 (2) and 53.7 (2)°, respectively, with the pyrazolone ring; the corresponding values in the P21/c polymorph are 7.5 (2) and 42.6 (2)°. Intra­molecular O—H⋯N and C—H⋯O hydrogen bonds are observed in the major disorder component. Adjacent molecules are linked through intermolecular O—H⋯O hydrogen bonds, forming dimers.

Related literature

For the P21/c polymorph of the title compound, see: Wang et al. (2007[Wang, L.-G., Zhang, C.-N., Yan, G.-B., Zheng, Y.-F. & Yang, M.-H. (2007). Acta Cryst. E63, o1245-o1246.]). For related structures, see: Duan et al. (2006[Duan, Z.-Y., Li, G., Zhang, W.-J., Han, E.-S. & Du, F.-Y. (2006). Acta Cryst. E62, o3103-o3104.]); Jing et al. (2006[Jing, Z.-L., Guo, M.-J., Chen, X. & Ming, Y. (2006). Acta Cryst. E62, o313-o315.]); Sun et al. (2006[Sun, Y.-X., Zhang, R., Wang, B.-L., Ding, D.-J. & Liu, S. (2006). Acta Cryst. E62, o4613-o4615.]); Wen (2005[Wen, P. (2005). Acta Cryst. E61, o2918-o2920.]); Zhang et al. (2007[Zhang, C.-N., Yang, M.-H., Yan, G.-B. & Zhou, Y.-M. (2007). Acta Cryst. E63, o1247-o1248.]); Zheng et al. (2006[Zheng, Y.-F., Yan, G.-B. & Gu, Y.-B. (2006). Acta Cryst. E62, o5134-o5135.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19N3O3

  • Mr = 337.37

  • Monoclinic, C 2/c

  • a = 30.581 (3) Å

  • b = 6.906 (2) Å

  • c = 17.059 (3) Å

  • β = 110.500 (2)°

  • V = 3374.6 (12) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 (2) K

  • 0.30 × 0.28 × 0.27 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.976

  • 9315 measured reflections

  • 3634 independent reflections

  • 2355 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.145

  • S = 1.01

  • 3634 reflections

  • 241 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N1 0.82 1.88 2.605 (2) 147
O1′—H1′⋯O3i 0.82 1.80 2.609 (6) 169
C7—H7⋯O3 0.93 2.33 3.006 (5) 129
Symmetry code: (i) [-x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The crystal structure of the title compound has been previously reported by Wang et al. (2007) in the monoclinic space group P21/c. We report here the structure of the second monoclinic polymorph of the title compound, in the space group C2/c.

In the title molecule (Fig. 1), the pyrazolone ring makes dihedral angles of 12.2 (2) and 53.7 (2)°, respectively, with the triply substituted C1–C6 benzene ring and the unsubstituted C13—C18 benzene ring; the corresponding values in the P21/c polymorph are 7.5 (2) and 42.6 (2)°. The bond lengths and angles are within normal ranges and comparable with those in related similar compounds (Duan et al., 2006; Jing et al., 2006; Zheng et al., 2006; Sun et al., 2006; Zhang et al., 2007; Wen, 2005). Intramolecular O—H···N and C—H···O hydrogen bonds (Table 1) are observed in the molecular structure.

Related literature top

For the P21/c polymorph of the title compound, see: Wang et al. (2007). For related literature, see: Duan et al. (2006); Jing et al. (2006); Sun et al. (2006); Wen (2005); Zhang et al. (2007); Zheng et al. (2006).

Experimental top

4-Methoxy-2-hydroxybenzaldehyde (152.1 mg, 1.0 mmol) and 4-aminoantipyrine (203.2 mg, 1.0 mmol) were added in methanol (60 ml). The mixture was refluxed for 30 min, then cooled to room temperature, yielding colourless solution. Colourless single crystals were formed when the solution was evaporated in air for several days.

Refinement top

The hydroxyl group is disordered over two positions with refined occupancies of 0.787 (4) and 0.213 (4). H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C–H distances of 0.93–0.96 Å, O–H distance of 0.82 Å, and with Uiso(H) set at 1.2Ueq(C) and 1.5Ueq(O and methyl C).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellisoids. Only the major disorder component is shown. Intramolecular hydrogen bonds are shown as dashed lines.
4-(2-hydroxy-4-methoxybenzylideneamino)-1,5-dimethyl-2-phenyl-1H- pyrazol-3(2H)-one top
Crystal data top
C19H19N3O3F(000) = 1424
Mr = 337.37Dx = 1.328 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2554 reflections
a = 30.581 (3) Åθ = 2.4–25.6°
b = 6.906 (2) ŵ = 0.09 mm1
c = 17.059 (3) ÅT = 298 K
β = 110.500 (2)°Block, colourless
V = 3374.6 (12) Å30.30 × 0.28 × 0.27 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
3634 independent reflections
Radiation source: fine-focus sealed tube2355 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 27.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 3638
Tmin = 0.973, Tmax = 0.976k = 88
9315 measured reflectionsl = 2021
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) = 0.145H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.071P)2 + 0.6977P]
where P = (Fo2 + 2Fc2)/3
3634 reflections(Δ/σ)max = 0.001
241 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C19H19N3O3V = 3374.6 (12) Å3
Mr = 337.37Z = 8
Monoclinic, C2/cMo Kα radiation
a = 30.581 (3) ŵ = 0.09 mm1
b = 6.906 (2) ÅT = 298 K
c = 17.059 (3) Å0.30 × 0.28 × 0.27 mm
β = 110.500 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3634 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
2355 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.976Rint = 0.037
9315 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 1.02Δρmax = 0.19 e Å3
3634 reflectionsΔρmin = 0.20 e Å3
241 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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)
O10.13337 (6)0.6567 (2)0.02029 (14)0.0720 (7)0.787 (4)
H10.16130.63370.04270.108*0.787 (4)
O1'0.1955 (2)1.2396 (10)0.0333 (4)0.071 (3)0.213 (4)
H1'0.18911.32410.06930.106*0.213 (4)
O20.03260 (5)1.1507 (2)0.13459 (11)0.0834 (5)
O30.31552 (5)0.96750 (18)0.13504 (9)0.0628 (4)
N10.22230 (5)0.7333 (2)0.08331 (9)0.0483 (4)
N20.32298 (5)0.5274 (2)0.23447 (9)0.0494 (4)
N30.34320 (5)0.6934 (2)0.21511 (9)0.0491 (4)
C10.16608 (6)0.9540 (2)0.00342 (11)0.0450 (4)
C20.12777 (7)0.8350 (3)0.01178 (12)0.0505 (5)
H20.13270.71250.01240.061*0.213 (4)
C30.08307 (7)0.8956 (3)0.05505 (13)0.0586 (5)
H30.05800.81440.06010.070*
C40.07548 (7)1.0762 (3)0.09092 (13)0.0573 (5)
C50.11288 (7)1.1968 (3)0.08392 (12)0.0586 (5)
H50.10781.31900.10840.070*
C60.15705 (6)1.1355 (3)0.04112 (12)0.0511 (5)
H60.18201.21710.03690.061*0.787 (4)
C70.21326 (6)0.8961 (2)0.04376 (11)0.0468 (4)
H70.23780.97800.04580.056*
C80.26761 (6)0.6861 (2)0.13421 (10)0.0437 (4)
C90.27825 (6)0.5207 (2)0.18071 (11)0.0458 (4)
C100.24772 (7)0.3533 (3)0.17836 (14)0.0658 (6)
H10A0.21790.37250.13510.099*
H10B0.24360.34110.23140.099*
H10C0.26180.23750.16700.099*
C110.35235 (7)0.3601 (3)0.26802 (13)0.0625 (6)
H11A0.33540.26770.28830.094*
H11B0.37980.40010.31320.094*
H11C0.36130.30190.22480.094*
C120.30866 (6)0.8026 (2)0.15627 (11)0.0468 (4)
C130.38321 (6)0.7784 (2)0.27470 (11)0.0460 (4)
C140.39069 (7)0.7743 (3)0.35949 (12)0.0559 (5)
H140.37030.70770.37950.067*
C150.42859 (8)0.8700 (3)0.41369 (14)0.0673 (6)
H150.43410.86650.47090.081*
C160.45828 (8)0.9701 (3)0.38483 (15)0.0717 (6)
H160.48361.03580.42210.086*
C170.45062 (7)0.9736 (3)0.30043 (15)0.0672 (6)
H170.47081.04240.28070.081*
C180.41342 (7)0.8764 (3)0.24504 (13)0.0545 (5)
H180.40870.87680.18810.065*
C190.00684 (9)1.0308 (4)0.1448 (3)0.1287 (14)
H19A0.00370.91200.17150.193*
H19B0.03471.09660.17880.193*
H19C0.00881.00300.09100.193*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0605 (11)0.0448 (11)0.1057 (17)0.0043 (9)0.0229 (11)0.0205 (10)
O1'0.056 (4)0.064 (4)0.079 (5)0.012 (3)0.005 (3)0.032 (4)
O20.0526 (8)0.0619 (9)0.1159 (14)0.0025 (7)0.0047 (8)0.0090 (9)
O30.0643 (8)0.0470 (8)0.0663 (9)0.0092 (7)0.0094 (7)0.0151 (6)
N10.0518 (9)0.0447 (8)0.0470 (9)0.0007 (7)0.0155 (7)0.0007 (7)
N20.0561 (9)0.0376 (8)0.0509 (9)0.0017 (7)0.0142 (8)0.0053 (7)
N30.0541 (9)0.0402 (8)0.0483 (9)0.0070 (7)0.0119 (7)0.0041 (7)
C10.0505 (10)0.0432 (9)0.0406 (10)0.0025 (8)0.0150 (8)0.0014 (8)
C20.0557 (11)0.0404 (10)0.0556 (11)0.0029 (8)0.0197 (9)0.0005 (8)
C30.0488 (11)0.0479 (11)0.0750 (14)0.0069 (9)0.0167 (10)0.0035 (10)
C40.0524 (11)0.0494 (11)0.0630 (13)0.0029 (9)0.0114 (10)0.0009 (9)
C50.0618 (12)0.0461 (11)0.0608 (13)0.0010 (9)0.0125 (10)0.0087 (9)
C60.0530 (11)0.0479 (10)0.0497 (11)0.0073 (9)0.0147 (9)0.0031 (8)
C70.0526 (10)0.0454 (10)0.0425 (10)0.0047 (8)0.0167 (8)0.0021 (8)
C80.0513 (10)0.0394 (9)0.0404 (9)0.0015 (8)0.0162 (8)0.0020 (7)
C90.0541 (10)0.0410 (9)0.0442 (10)0.0015 (8)0.0195 (9)0.0011 (8)
C100.0708 (13)0.0508 (11)0.0740 (14)0.0116 (10)0.0229 (12)0.0091 (10)
C110.0688 (13)0.0471 (11)0.0632 (13)0.0063 (10)0.0127 (11)0.0108 (9)
C120.0562 (11)0.0402 (9)0.0413 (10)0.0026 (8)0.0138 (9)0.0011 (8)
C130.0453 (10)0.0397 (9)0.0487 (11)0.0024 (8)0.0111 (9)0.0004 (8)
C140.0554 (11)0.0612 (12)0.0505 (11)0.0039 (10)0.0180 (10)0.0004 (9)
C150.0663 (13)0.0772 (14)0.0496 (12)0.0062 (12)0.0091 (11)0.0061 (10)
C160.0600 (13)0.0742 (15)0.0689 (15)0.0139 (11)0.0075 (11)0.0059 (12)
C170.0565 (12)0.0623 (13)0.0838 (16)0.0101 (10)0.0255 (12)0.0009 (12)
C180.0590 (11)0.0527 (11)0.0536 (11)0.0026 (9)0.0223 (10)0.0005 (9)
C190.0503 (14)0.087 (2)0.211 (4)0.0084 (14)0.0024 (18)0.023 (2)
Geometric parameters (Å, º) top
O1—C21.333 (2)C7—H70.93
O1—H10.82C8—C91.363 (2)
O1'—C61.345 (6)C8—C121.426 (2)
O1'—H1'0.82C9—C101.478 (2)
O2—C41.362 (2)C10—H10A0.96
O2—C191.422 (3)C10—H10B0.96
O3—C121.235 (2)C10—H10C0.96
N1—C71.291 (2)C11—H11A0.96
N1—C81.392 (2)C11—H11B0.96
N2—C91.355 (2)C11—H11C0.96
N2—N31.3959 (19)C13—C181.376 (3)
N2—C111.452 (2)C13—C141.383 (3)
N3—C121.396 (2)C14—C151.373 (3)
N3—C131.416 (2)C14—H140.93
C1—C61.392 (2)C15—C161.363 (3)
C1—C21.397 (2)C15—H150.93
C1—C71.441 (2)C16—C171.376 (3)
C2—C31.372 (3)C16—H160.93
C2—H20.93C17—C181.373 (3)
C3—C41.373 (3)C17—H170.93
C3—H30.93C18—H180.93
C4—C51.386 (3)C19—H19A0.96
C5—C61.359 (3)C19—H19B0.96
C5—H50.93C19—H19C0.96
C6—H60.93
C2—O1—H1109.5C8—C9—C10128.31 (17)
C6—O1'—H1'109.5C9—C10—H10A109.5
C4—O2—C19117.40 (17)C9—C10—H10B109.5
C7—N1—C8120.96 (15)H10A—C10—H10B109.5
C9—N2—N3107.07 (13)C9—C10—H10C109.5
C9—N2—C11125.34 (14)H10A—C10—H10C109.5
N3—N2—C11118.86 (14)H10B—C10—H10C109.5
N2—N3—C12109.12 (13)N2—C11—H11A109.5
N2—N3—C13120.92 (14)N2—C11—H11B109.5
C12—N3—C13122.55 (14)H11A—C11—H11B109.5
C6—C1—C2117.34 (16)N2—C11—H11C109.5
C6—C1—C7120.37 (16)H11A—C11—H11C109.5
C2—C1—C7122.27 (16)H11B—C11—H11C109.5
O1—C2—C3117.58 (18)O3—C12—N3123.06 (16)
O1—C2—C1121.24 (18)O3—C12—C8131.86 (17)
C3—C2—C1121.16 (17)N3—C12—C8105.01 (14)
C3—C2—H2119.4C18—C13—C14120.51 (17)
C1—C2—H2119.4C18—C13—N3117.56 (17)
C2—C3—C4119.87 (18)C14—C13—N3121.82 (17)
C2—C3—H3120.1C15—C14—C13119.09 (19)
C4—C3—H3120.1C15—C14—H14120.5
O2—C4—C3124.53 (18)C13—C14—H14120.5
O2—C4—C5115.33 (17)C16—C15—C14120.8 (2)
C3—C4—C5120.14 (18)C16—C15—H15119.6
C6—C5—C4119.62 (17)C14—C15—H15119.6
C6—C5—H5120.2C15—C16—C17119.7 (2)
C4—C5—H5120.2C15—C16—H16120.1
O1'—C6—C5123.9 (3)C17—C16—H16120.1
O1'—C6—C1114.2 (3)C18—C17—C16120.5 (2)
C5—C6—C1121.86 (17)C18—C17—H17119.7
C5—C6—H6119.1C16—C17—H17119.7
C1—C6—H6119.1C17—C18—C13119.2 (2)
N1—C7—C1121.53 (17)C17—C18—H18120.4
N1—C7—H7119.2C13—C18—H18120.4
C1—C7—H7119.2O2—C19—H19A109.5
C9—C8—N1122.81 (16)O2—C19—H19B109.5
C9—C8—C12108.09 (15)H19A—C19—H19B109.5
N1—C8—C12128.62 (15)O2—C19—H19C109.5
N2—C9—C8110.13 (15)H19A—C19—H19C109.5
N2—C9—C10121.55 (16)H19B—C19—H19C109.5
C9—N2—N3—C127.87 (18)C11—N2—C9—C8153.47 (18)
C11—N2—N3—C12157.19 (16)N3—N2—C9—C10174.23 (17)
C9—N2—N3—C13158.51 (16)C11—N2—C9—C1027.5 (3)
C11—N2—N3—C1352.2 (2)N1—C8—C9—N2169.67 (15)
C6—C1—C2—O1178.03 (19)C12—C8—C9—N23.0 (2)
C7—C1—C2—O13.5 (3)N1—C8—C9—C109.3 (3)
C6—C1—C2—C30.4 (3)C12—C8—C9—C10177.97 (18)
C7—C1—C2—C3178.12 (18)N2—N3—C12—O3171.32 (17)
O1—C2—C3—C4178.5 (2)C13—N3—C12—O321.3 (3)
C1—C2—C3—C40.1 (3)N2—N3—C12—C85.92 (18)
C19—O2—C4—C31.2 (4)C13—N3—C12—C8155.98 (16)
C19—O2—C4—C5178.8 (2)C9—C8—C12—O3175.1 (2)
C2—C3—C4—O2179.54 (19)N1—C8—C12—O32.9 (3)
C2—C3—C4—C50.4 (3)C9—C8—C12—N31.84 (19)
O2—C4—C5—C6179.70 (19)N1—C8—C12—N3174.00 (16)
C3—C4—C5—C60.2 (3)N2—N3—C13—C18150.64 (16)
C4—C5—C6—O1'177.8 (5)C12—N3—C13—C1862.7 (2)
C4—C5—C6—C10.2 (3)N2—N3—C13—C1433.2 (2)
C2—C1—C6—O1'177.6 (4)C12—N3—C13—C14113.5 (2)
C7—C1—C6—O1'3.8 (5)C18—C13—C14—C150.2 (3)
C2—C1—C6—C50.6 (3)N3—C13—C14—C15175.85 (18)
C7—C1—C6—C5177.99 (18)C13—C14—C15—C160.8 (3)
C8—N1—C7—C1174.67 (15)C14—C15—C16—C170.8 (3)
C6—C1—C7—N1175.94 (17)C15—C16—C17—C180.3 (3)
C2—C1—C7—N12.5 (3)C16—C17—C18—C131.3 (3)
C7—N1—C8—C9176.18 (17)C14—C13—C18—C171.3 (3)
C7—N1—C8—C125.1 (3)N3—C13—C18—C17174.94 (18)
N3—N2—C9—C86.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.882.605 (2)147
O1—H1···O3i0.821.802.609 (6)169
C7—H7···O30.932.333.006 (5)129
Symmetry code: (i) x+1/2, y+5/2, z.

Experimental details

Crystal data
Chemical formulaC19H19N3O3
Mr337.37
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)30.581 (3), 6.906 (2), 17.059 (3)
β (°) 110.500 (2)
V3)3374.6 (12)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.28 × 0.27
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.973, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
9315, 3634, 2355
Rint0.037
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.145, 1.02
No. of reflections3634
No. of parameters241
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.20

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.882.605 (2)147
O1'—H1'···O3i0.821.802.609 (6)169
C7—H7···O30.932.333.006 (5)129
Symmetry code: (i) x+1/2, y+5/2, z.
 

References

First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDuan, Z.-Y., Li, G., Zhang, W.-J., Han, E.-S. & Du, F.-Y. (2006). Acta Cryst. E62, o3103–o3104.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationJing, Z.-L., Guo, M.-J., Chen, X. & Ming, Y. (2006). Acta Cryst. E62, o313–o315.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSun, Y.-X., Zhang, R., Wang, B.-L., Ding, D.-J. & Liu, S. (2006). Acta Cryst. E62, o4613–o4615.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWang, L.-G., Zhang, C.-N., Yan, G.-B., Zheng, Y.-F. & Yang, M.-H. (2007). Acta Cryst. E63, o1245–o1246.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWen, P. (2005). Acta Cryst. E61, o2918–o2920.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationZhang, C.-N., Yang, M.-H., Yan, G.-B. & Zhou, Y.-M. (2007). Acta Cryst. E63, o1247–o1248.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationZheng, Y.-F., Yan, G.-B. & Gu, Y.-B. (2006). Acta Cryst. E62, o5134–o5135.  Web of Science CSD CrossRef 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 10| October 2008| Pages o1965-o1966
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds