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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1992.
Published online 2008 September 24. doi:  10.1107/S1600536808022484
PMCID: PMC2959455

1,2-Diphenyl­ethane-1,2-diyl diiso­nico­tinate monohydrate1

Abstract

In the novel title compound, C26H20N2O4·H2O, the two phenyl rings make a dihedral angle of 45.3 (1)° with each other, and the dihedral angle between the two pyridyl planes is 69.8 (1)°.

Related literature

For general background, see: Aspinall et al. (2003 [triangle]); Takenaka et al. (2006 [triangle]); MacMahon et al. (2001 [triangle]); Schuster et al. (2005 [triangle]). For related structures, see: Shi et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1992-scheme1.jpg

Experimental

Crystal data

  • C26H20N2O4·H2O
  • M r = 442.46
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1992-efi1.jpg
  • a = 11.925 (10) Å
  • b = 5.826 (5) Å
  • c = 17.787 (15) Å
  • β = 105.629 (10)°
  • V = 1190.1 (17) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 291 (2) K
  • 0.32 × 0.24 × 0.22 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker,2000 [triangle]) T min = 0.979, T max = 0.981
  • 6535 measured reflections
  • 2566 independent reflections
  • 1816 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.086
  • S = 1.10
  • 2566 reflections
  • 304 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks z0612, I. DOI: 10.1107/S1600536808022484/sg2251sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022484/sg2251Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Natural Science Foundation of China (No. 20272019) and the Key Laboratory of Fine Petrochemical Engineering of Jiangsu Province (KF0503) for financial support.

supplementary crystallographic information

Comment

Synthesis of chiral molecules containing pyridine rings has attracted considerable attention in recent years (Aspinall,et al., 2003; Takenaka,et al., 2006; MacMahon, et al., 2001; Schuster, et al., 2005). In the title compound, (I), C26H20NO2, all bond lengths and angles show normal values (Shi, et al., 2006). The chiral molecule (Figure 1) consists of two benzene rings and two pyridine rings. The dihedral angle between the two benzene ring is 45.28°. The torsion angle C2—C1—C7—O2 is -44.2 (2)°; the torsional angle The packing arrangement in a unit cell of the title molecule is shown in Figure 2.

Experimental

The title compound, was synthesized by the reaction of trans-1,2-stilbene with nicotinic acid in dichloromethane. The single crystals of (I) suitable for X-ray diffraction were obtained from an ethanol solution by slow evaporation.

Refinement

The H atoms bonded to N atom were located from difference density maps and refined isotropically. The H atoms bonded to C atoms were located geometrically and treated as riding, with C—H distances of 0.95–1.00 Å and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for others. Due to the absence of heavy atoms corresponding to Si, it was impossible to determine the absolute configuration in this case. At this stage, the Friedel pairs were merged.

Figures

Fig. 1.
The molecular structure of (I), showing 20% probability displacement ellipsoids.
Fig. 2.
The molecular packing diagram in the crystal for (I).

Crystal data

C26H20N2O4·H2OF(000) = 464
Mr = 442.46Dx = 1.235 Mg m3
Monoclinic, P21Melting point: 327 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 11.925 (10) ÅCell parameters from 1142 reflections
b = 5.826 (5) Åθ = 2.4–21.6°
c = 17.787 (15) ŵ = 0.09 mm1
β = 105.629 (10)°T = 291 K
V = 1190.1 (17) Å3Acicular, colorless
Z = 20.32 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer2566 independent reflections
Radiation source: sealed tube1816 reflections with I > 2σ(I)
graphiteRint = 0.024
phi and ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker,2000)h = −14→14
Tmin = 0.979, Tmax = 0.981k = −7→7
6535 measured reflectionsl = −21→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 1.10w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3
2566 reflections(Δ/σ)max < 0.001
304 parametersΔρmax = 0.13 e Å3
1 restraintΔρmin = −0.11 e Å3

Special details

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 > 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)

xyzUiso*/Ueq
C10.1366 (3)0.0950 (8)0.1997 (2)0.0617 (9)
H10.18430.01980.24260.074*
C20.0250 (3)0.0040 (7)0.1606 (2)0.0610 (10)
H20.0002−0.13190.17840.073*
C3−0.0446 (3)0.1107 (7)0.0988 (2)0.0658 (10)
H3−0.11710.04860.07440.079*
C4−0.0107 (3)0.3060 (7)0.0718 (2)0.0644 (10)
H4−0.05980.37830.02870.077*
C50.1006 (3)0.4042 (7)0.1088 (2)0.0604 (9)
H50.12370.53950.08950.072*
C60.1729 (3)0.2994 (6)0.17230 (19)0.0526 (8)
C70.2931 (2)0.3938 (6)0.20841 (16)0.0479 (8)
H70.29800.55240.19120.058*
C80.3874 (3)0.2465 (7)0.18741 (17)0.0520 (8)
H80.38540.08920.20650.062*
C90.3699 (2)0.2474 (6)0.10007 (17)0.0454 (7)
C100.3172 (3)0.0645 (7)0.05519 (19)0.0575 (9)
H100.2938−0.06210.07900.069*
C110.2988 (3)0.0677 (7)−0.0256 (2)0.0592 (9)
H110.2647−0.0576−0.05550.071*
C120.3315 (3)0.2587 (7)−0.06095 (19)0.0545 (8)
H120.31650.2639−0.11500.065*
C130.3855 (3)0.4387 (7)−0.01715 (19)0.0560 (9)
H130.40930.5640−0.04140.067*
C140.4059 (2)0.4372 (6)0.06493 (19)0.0511 (8)
H140.44270.56040.09490.061*
C150.3427 (3)0.5843 (7)0.3341 (2)0.0534 (8)
C160.3422 (3)0.5479 (7)0.4175 (2)0.0586 (9)
C170.2955 (3)0.3621 (7)0.4423 (2)0.0629 (10)
H170.26440.24690.40660.076*
C180.2919 (3)0.3359 (7)0.5200 (2)0.0611 (10)
H180.25950.20510.53560.073*
C190.3806 (3)0.6880 (6)0.5480 (2)0.0611 (10)
H190.40730.80480.58400.073*
C200.3910 (3)0.7229 (7)0.4693 (2)0.0639 (10)
H200.42700.85070.45480.077*
C210.5955 (3)0.2419 (6)0.22411 (18)0.0478 (8)
C220.7001 (3)0.3845 (6)0.25533 (17)0.0504 (8)
C230.7001 (3)0.5913 (7)0.29022 (18)0.0551 (9)
H230.63120.65130.29710.066*
C240.8028 (3)0.7121 (7)0.3155 (2)0.0608 (10)
H240.80090.85280.33980.073*
C250.9004 (3)0.4385 (8)0.2745 (2)0.0661 (10)
H250.97060.38180.26900.079*
C260.8048 (3)0.2999 (7)0.2472 (2)0.0590 (9)
H260.81010.15790.22450.071*
N10.3370 (3)0.5066 (6)0.57225 (18)0.0654 (8)
N20.9046 (3)0.6389 (6)0.30715 (18)0.0660 (9)
O10.31042 (17)0.3875 (4)0.29344 (11)0.0516 (6)
O20.36767 (19)0.7536 (5)0.30737 (14)0.0629 (7)
O30.49642 (18)0.3587 (4)0.22757 (12)0.0531 (6)
O40.59297 (19)0.0481 (5)0.19752 (13)0.0587 (6)
O50.0848 (2)0.9233 (6)0.40864 (18)0.0779 (9)
H5A0.059 (4)0.815 (9)0.424 (3)0.093*
H5B0.047 (3)0.947 (8)0.362 (3)0.093*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.061 (2)0.065 (3)0.058 (2)0.0020 (18)0.0136 (18)0.0043 (19)
C20.063 (2)0.059 (3)0.061 (2)−0.0087 (17)0.0178 (19)−0.0038 (18)
C30.062 (2)0.069 (3)0.064 (2)−0.010 (2)0.0140 (19)−0.015 (2)
C40.060 (2)0.067 (3)0.062 (2)0.0080 (19)0.0089 (18)−0.005 (2)
C50.0522 (18)0.063 (2)0.064 (2)0.0058 (18)0.0123 (16)−0.001 (2)
C60.0556 (19)0.057 (2)0.0475 (18)−0.0030 (16)0.0178 (15)−0.0043 (17)
C70.0533 (17)0.057 (2)0.0308 (15)0.0098 (16)0.0067 (13)0.0048 (15)
C80.0542 (18)0.062 (2)0.0420 (17)−0.0031 (16)0.0175 (15)0.0039 (16)
C90.0432 (15)0.053 (2)0.0411 (18)0.0037 (15)0.0136 (14)−0.0001 (16)
C100.0568 (19)0.065 (2)0.050 (2)−0.0001 (18)0.0130 (16)−0.0030 (19)
C110.061 (2)0.061 (2)0.054 (2)−0.0055 (19)0.0127 (17)−0.0121 (19)
C120.0562 (18)0.067 (2)0.0429 (19)0.0085 (18)0.0180 (16)0.0023 (18)
C130.0502 (17)0.064 (2)0.0525 (19)0.0065 (17)0.0121 (15)0.0081 (18)
C140.0488 (17)0.059 (2)0.0481 (18)−0.0065 (17)0.0179 (14)−0.0004 (17)
C150.0568 (19)0.052 (2)0.053 (2)0.0120 (17)0.0188 (16)0.0071 (19)
C160.064 (2)0.062 (2)0.0490 (18)−0.0077 (18)0.0140 (16)−0.0006 (18)
C170.066 (2)0.066 (3)0.055 (2)−0.0181 (18)0.0140 (18)−0.0070 (19)
C180.067 (2)0.059 (2)0.055 (2)−0.0162 (18)0.0121 (17)0.0051 (18)
C190.065 (2)0.060 (2)0.057 (2)−0.0133 (19)0.0159 (17)−0.0154 (19)
C200.0620 (19)0.063 (2)0.065 (2)−0.0051 (18)0.0138 (18)−0.0064 (19)
C210.0522 (17)0.058 (2)0.0351 (16)0.0071 (16)0.0142 (14)0.0124 (16)
C220.0616 (19)0.060 (2)0.0320 (15)0.0033 (17)0.0170 (14)0.0072 (16)
C230.060 (2)0.065 (3)0.0394 (17)0.0064 (17)0.0124 (15)0.0017 (17)
C240.060 (2)0.063 (3)0.058 (2)0.0028 (18)0.0136 (18)−0.0088 (18)
C250.063 (2)0.064 (3)0.072 (2)−0.001 (2)0.0174 (19)−0.011 (2)
C260.0579 (19)0.061 (2)0.058 (2)−0.0075 (17)0.0152 (17)−0.0077 (18)
N10.0718 (19)0.066 (2)0.0574 (17)−0.0158 (16)0.0152 (15)−0.0097 (16)
N20.0662 (18)0.066 (2)0.065 (2)0.0032 (15)0.0164 (15)−0.0170 (17)
O10.0563 (13)0.0607 (16)0.0372 (12)−0.0064 (12)0.0117 (10)0.0014 (11)
O20.0610 (14)0.0649 (17)0.0592 (15)−0.0069 (13)0.0100 (12)0.0042 (14)
O30.0570 (12)0.0594 (15)0.0429 (11)0.0088 (11)0.0134 (10)−0.0027 (11)
O40.0579 (13)0.0690 (17)0.0498 (13)0.0184 (13)0.0153 (10)−0.0072 (13)
O50.0623 (17)0.073 (2)0.079 (2)−0.0134 (15)−0.0127 (14)0.0160 (17)

Geometric parameters (Å, °)

C1—C61.399 (5)C15—O21.168 (4)
C1—C21.427 (5)C15—O11.354 (4)
C1—H10.9300C15—C161.502 (5)
C2—C31.339 (5)C16—C171.344 (5)
C2—H20.9300C16—C201.392 (5)
C3—C41.339 (6)C17—C181.402 (5)
C3—H30.9300C17—H170.9300
C4—C51.433 (5)C18—N11.369 (5)
C4—H40.9300C18—H180.9300
C5—C61.367 (5)C19—N11.302 (5)
C5—H50.9300C19—C201.452 (5)
C6—C71.507 (4)C19—H190.9300
C7—O11.471 (3)C20—H200.9300
C7—C81.538 (4)C21—O41.221 (5)
C7—H70.9800C21—O31.379 (4)
C8—O31.459 (4)C21—C221.477 (5)
C8—C91.511 (4)C22—C231.355 (5)
C8—H80.9800C22—C261.386 (4)
C9—C101.377 (5)C23—C241.379 (5)
C9—C141.394 (5)C23—H230.9300
C10—C111.394 (5)C24—N21.333 (4)
C10—H100.9300C24—H240.9300
C11—C121.385 (5)C25—N21.298 (5)
C11—H110.9300C25—C261.374 (5)
C12—C131.361 (5)C25—H250.9300
C12—H120.9300C26—H260.9300
C13—C141.414 (5)O5—H5A0.78 (5)
C13—H130.9300O5—H5B0.84 (4)
C14—H140.9300
C6—C1—C2118.9 (3)C9—C14—C13118.7 (3)
C6—C1—H1120.6C9—C14—H14120.7
C2—C1—H1120.6C13—C14—H14120.7
C3—C2—C1121.2 (4)O2—C15—O1124.4 (3)
C3—C2—H2119.4O2—C15—C16126.2 (4)
C1—C2—H2119.4O1—C15—C16109.4 (3)
C4—C3—C2120.6 (4)C17—C16—C20120.7 (3)
C4—C3—H3119.7C17—C16—C15123.3 (3)
C2—C3—H3119.7C20—C16—C15116.0 (4)
C3—C4—C5120.4 (4)C16—C17—C18122.4 (3)
C3—C4—H4119.8C16—C17—H17118.8
C5—C4—H4119.8C18—C17—H17118.8
C6—C5—C4120.1 (4)N1—C18—C17118.6 (3)
C6—C5—H5119.9N1—C18—H18120.7
C4—C5—H5119.9C17—C18—H18120.7
C5—C6—C1118.8 (3)N1—C19—C20125.3 (3)
C5—C6—C7120.3 (3)N1—C19—H19117.3
C1—C6—C7120.7 (3)C20—C19—H19117.3
O1—C7—C6106.5 (2)C16—C20—C19113.9 (4)
O1—C7—C8109.0 (2)C16—C20—H20123.0
C6—C7—C8111.5 (3)C19—C20—H20123.0
O1—C7—H7109.9O4—C21—O3122.8 (3)
C6—C7—H7109.9O4—C21—C22126.6 (3)
C8—C7—H7109.9O3—C21—C22110.6 (3)
O3—C8—C9111.1 (2)C23—C22—C26118.4 (3)
O3—C8—C7104.2 (3)C23—C22—C21124.6 (3)
C9—C8—C7109.9 (3)C26—C22—C21117.0 (3)
O3—C8—H8110.5C22—C23—C24119.6 (3)
C9—C8—H8110.5C22—C23—H23120.2
C7—C8—H8110.5C24—C23—H23120.2
C10—C9—C14120.1 (3)N2—C24—C23123.8 (4)
C10—C9—C8120.6 (3)N2—C24—H24118.1
C14—C9—C8119.3 (3)C23—C24—H24118.1
C9—C10—C11120.5 (4)N2—C25—C26128.0 (4)
C9—C10—H10119.7N2—C25—H25116.0
C11—C10—H10119.7C26—C25—H25116.0
C12—C11—C10119.6 (3)C25—C26—C22116.0 (3)
C12—C11—H11120.2C25—C26—H26122.0
C10—C11—H11120.2C22—C26—H26122.0
C13—C12—C11120.5 (3)C19—N1—C18118.9 (3)
C13—C12—H12119.8C25—N2—C24114.2 (4)
C11—C12—H12119.8C15—O1—C7117.9 (3)
C12—C13—C14120.6 (3)C21—O3—C8114.7 (3)
C12—C13—H13119.7H5A—O5—H5B108 (4)
C14—C13—H13119.7

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5B···N2i0.84 (4)2.48 (5)2.921 (4)113 (4)

Symmetry codes: (i) x−1, y, z.

Footnotes

1Contribution No 20272019.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2251).

References

  • Aspinall, H. C., Greeves, N. & McIver, E. G. (2003). Tetrahedron, 59, 10453–10463.
  • Bruker, (2000). SMART, SAINT and SADABS Bruker AXS Inc. Madison, Wisconsin, USA.
  • MacMahon, S. R., Fong, P. S., Baran, S. I., Wilson, S. R. & Schuster, D. I. (2001). J. Org. Chem.66, 5449–5455. [PubMed]
  • Schuster, C., Knollmueller, M. & Gaertner, P. (2005). Tetrahedron Asymmetry, 16, 2631–2647.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shi, S.-M., Jia, B., Wu, Y., Liu, X.-D. & Hu, Z.-Q. (2006). Acta Cryst. E62, o2278–o2280.
  • Takenaka, Y., Ito, H., Hasegawa, M. & Iguchi, K. (2006). Tetrahedron, 62, 3380–3388.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography