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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o1884.
Published online 2010 July 3. doi:  10.1107/S1600536810025109
PMCID: PMC3007454

4′-(Morpholino­meth­yl)biphenyl-2-carbonitrile

Abstract

In the title compound, C18H18N2O, the morpholine ring adopts a chair conformation and the dihedral angle between the aromatic rings is 49.16 (7)°. In the crystal, weak C—H(...)π inter­actions may help to establish the packing.

Related literature

For background to ligands related to the title compound, see: Li et al. (2008 [triangle]); Zhang et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1884-scheme1.jpg

Experimental

Crystal data

  • C18H18N2O
  • M r = 278.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1884-efi1.jpg
  • a = 10.924 (6) Å
  • b = 10.891 (5) Å
  • c = 12.943 (7) Å
  • β = 93.269 (7)°
  • V = 1537.4 (13) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.20 × 0.20 × 0.20 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.985, T max = 0.985
  • 16364 measured reflections
  • 3493 independent reflections
  • 2757 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.138
  • S = 1.10
  • 3493 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025109/hb5523sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025109/hb5523Isup2.hkl

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

Acknowledgments

The author is grateful to the starter fund of Southeast University for financial support to purchase the X-ray diffractometer.

supplementary crystallographic information

Experimental

A solution of 4'-bromomethylbiphenyl-2-carbonitrile (10 mmol) in acetone was added dropwise to a mixture of morpholine (10 mmol) and potassium carbonate anhydrous (10 mmol) at 331 K with stirring for 6 h; the reaction solution was then filted. Colourless prisms of (I) were formed after several weeks by slow evaporation of the solvent at room temperature. The compound shows no dielectric irregularity in the temperature range of 93–352 K.

Refinement

Positional parameters of all the H atoms were calculated geometrically and were allowed to ride on the C, N atoms to which they are bonded, with C—H =0.93 to 0.97 Å, Uiso(H) = 1.2 Ueq(C), N—H = 0.89 Å, Uiso(H)= 1.5 Ueq(N).

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level, and all H atoms have been omitted for clarity.
Fig. 2.
A view of the packing of the title compound, stacking along the a axis. Dashed lines indicate hydrogen bonds.

Crystal data

C18H18N2OF(000) = 592
Mr = 278.34Dx = 1.203 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3548 reflections
a = 10.924 (6) Åθ = 2.4–27.4°
b = 10.891 (5) ŵ = 0.08 mm1
c = 12.943 (7) ÅT = 293 K
β = 93.269 (7)°Prism, colourless
V = 1537.4 (13) Å30.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer3493 independent reflections
Radiation source: fine-focus sealed tube2757 reflections with I > 2σ(I)
graphiteRint = 0.042
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 2.4°
ω scansh = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −14→14
Tmin = 0.985, Tmax = 0.985l = −16→16
16364 measured reflections

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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0609P)2 + 0.152P] where P = (Fo2 + 2Fc2)/3
3493 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = −0.14 e Å3

Special details

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)

xyzUiso*/Ueq
C51.14259 (16)0.82069 (14)0.13367 (14)0.0528 (4)
H5A1.13250.83040.06000.063*
H5B1.22880.82260.15270.063*
C90.97335 (13)1.12626 (12)0.28571 (10)0.0365 (3)
N21.09293 (12)0.70241 (11)0.16311 (10)0.0448 (3)
C120.92172 (13)1.23165 (12)0.34199 (11)0.0380 (3)
C170.82704 (13)1.30573 (13)0.29907 (11)0.0395 (3)
C71.04111 (15)0.91490 (13)0.28539 (12)0.0459 (4)
H7A1.05010.83740.32030.055*
C101.01117 (14)1.13799 (13)0.18511 (11)0.0420 (3)
H10A1.00061.21500.14970.050*
C61.08033 (14)0.92683 (13)0.18531 (12)0.0421 (4)
O11.00038 (13)0.45991 (10)0.13465 (10)0.0654 (4)
C160.78280 (14)1.40534 (14)0.35368 (13)0.0484 (4)
H16A0.72051.45420.32380.058*
C180.76939 (14)1.27795 (14)0.19868 (13)0.0471 (4)
C111.06370 (14)1.03952 (14)0.13615 (12)0.0452 (4)
H11A1.08851.04910.06660.054*
C80.98879 (15)1.01272 (13)0.33456 (12)0.0439 (4)
H8A0.96311.00250.40380.053*
C130.96826 (16)1.26019 (14)0.44174 (12)0.0493 (4)
H13A1.03351.21140.47310.059*
C40.97391 (15)0.67913 (14)0.11041 (14)0.0505 (4)
H4A0.98310.67230.03730.061*
H4B0.91950.74630.12190.061*
C140.92365 (18)1.35790 (16)0.49598 (13)0.0576 (5)
H14A0.95611.37490.56500.069*
C150.83137 (17)1.43118 (15)0.45173 (14)0.0556 (4)
H15A0.80151.49980.48940.067*
N10.71962 (15)1.25687 (16)0.12030 (12)0.0694 (5)
C11.17405 (17)0.59987 (15)0.14313 (16)0.0639 (5)
H1A1.25320.61370.17730.077*
H1B1.18430.59230.07020.077*
C30.92168 (18)0.56140 (15)0.14975 (17)0.0666 (5)
H3A0.90900.57030.22220.080*
H3B0.84350.54600.11440.080*
C21.1182 (2)0.48294 (16)0.18227 (17)0.0732 (6)
H2A1.17160.41510.17010.088*
H2B1.11130.49010.25560.088*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C50.0498 (10)0.0402 (8)0.0696 (11)−0.0040 (7)0.0130 (8)−0.0107 (7)
C90.0376 (8)0.0340 (7)0.0373 (7)−0.0013 (6)−0.0025 (6)−0.0027 (6)
N20.0462 (7)0.0338 (6)0.0542 (8)0.0031 (5)0.0015 (6)−0.0064 (5)
C120.0419 (8)0.0338 (7)0.0384 (7)−0.0034 (6)0.0017 (6)−0.0004 (6)
C170.0372 (8)0.0379 (8)0.0434 (8)−0.0038 (6)0.0033 (6)−0.0002 (6)
C70.0559 (10)0.0331 (8)0.0487 (9)−0.0002 (6)0.0027 (7)0.0025 (6)
C100.0462 (9)0.0363 (7)0.0437 (8)0.0003 (6)0.0034 (6)0.0035 (6)
C60.0402 (8)0.0353 (8)0.0511 (9)−0.0045 (6)0.0041 (6)−0.0060 (6)
O10.0846 (10)0.0374 (6)0.0742 (9)−0.0038 (6)0.0041 (7)−0.0066 (5)
C160.0425 (9)0.0417 (8)0.0617 (10)0.0020 (6)0.0078 (7)−0.0027 (7)
C180.0405 (9)0.0480 (9)0.0525 (9)0.0043 (7)−0.0011 (7)−0.0003 (7)
C110.0488 (9)0.0445 (9)0.0431 (8)−0.0032 (7)0.0101 (7)0.0000 (6)
C80.0540 (9)0.0395 (8)0.0381 (8)−0.0013 (7)0.0018 (6)0.0007 (6)
C130.0590 (10)0.0444 (9)0.0433 (8)0.0013 (7)−0.0068 (7)−0.0042 (7)
C40.0464 (9)0.0406 (8)0.0644 (10)0.0029 (7)0.0015 (7)−0.0049 (7)
C140.0777 (13)0.0520 (10)0.0428 (9)−0.0052 (9)0.0003 (8)−0.0113 (7)
C150.0628 (11)0.0451 (9)0.0603 (11)−0.0028 (8)0.0164 (8)−0.0150 (8)
N10.0603 (10)0.0852 (12)0.0608 (10)0.0075 (8)−0.0139 (8)−0.0089 (8)
C10.0558 (11)0.0444 (10)0.0903 (14)0.0115 (8)−0.0053 (10)−0.0108 (9)
C30.0625 (12)0.0464 (10)0.0923 (15)−0.0088 (8)0.0161 (10)−0.0087 (9)
C20.0919 (16)0.0431 (10)0.0824 (14)0.0137 (10)−0.0138 (12)−0.0018 (9)

Geometric parameters (Å, °)

C5—N21.457 (2)C16—C151.376 (2)
C5—C61.516 (2)C16—H16A0.9300
C5—H5A0.9600C18—N11.146 (2)
C5—H5B0.9601C11—H11A0.9601
C9—C101.394 (2)C8—H8A0.9599
C9—C81.395 (2)C13—C141.379 (2)
C9—C121.4877 (19)C13—H13A0.9600
N2—C41.456 (2)C4—C31.504 (2)
N2—C11.458 (2)C4—H4A0.9600
C12—C131.395 (2)C4—H4B0.9600
C12—C171.401 (2)C14—C151.384 (3)
C17—C161.396 (2)C14—H14A0.9600
C17—C181.443 (2)C15—H15A0.9600
C7—C81.381 (2)C1—C21.512 (3)
C7—C61.393 (2)C1—H1A0.9600
C7—H7A0.9601C1—H1B0.9599
C10—C111.387 (2)C3—H3A0.9601
C10—H10A0.9600C3—H3B0.9599
C6—C111.390 (2)C2—H2A0.9600
O1—C21.417 (3)C2—H2B0.9599
O1—C31.421 (2)
N2—C5—C6112.08 (13)C7—C8—H8A119.4
N2—C5—H5A109.5C9—C8—H8A119.4
C6—C5—H5A109.0C14—C13—C12121.48 (15)
N2—C5—H5B109.0C14—C13—H13A119.2
C6—C5—H5B109.2C12—C13—H13A119.3
H5A—C5—H5B108.0N2—C4—C3109.62 (14)
C10—C9—C8118.04 (13)N2—C4—H4A109.6
C10—C9—C12121.83 (12)C3—C4—H4A109.3
C8—C9—C12120.10 (13)N2—C4—H4B109.8
C4—N2—C5111.55 (13)C3—C4—H4B110.3
C4—N2—C1108.61 (12)H4A—C4—H4B108.2
C5—N2—C1113.06 (14)C13—C14—C15120.30 (15)
C13—C12—C17117.41 (13)C13—C14—H14A120.0
C13—C12—C9119.78 (13)C15—C14—H14A119.7
C17—C12—C9122.81 (13)C16—C15—C14119.81 (15)
C16—C17—C12121.04 (14)C16—C15—H15A120.2
C16—C17—C18118.22 (14)C14—C15—H15A120.0
C12—C17—C18120.70 (13)N2—C1—C2108.95 (16)
C8—C7—C6120.91 (14)N2—C1—H1A109.8
C8—C7—H7A119.7C2—C1—H1A110.3
C6—C7—H7A119.4N2—C1—H1B110.3
C11—C10—C9120.56 (13)C2—C1—H1B109.2
C11—C10—H10A120.0H1A—C1—H1B108.3
C9—C10—H10A119.5O1—C3—C4111.87 (15)
C11—C6—C7117.96 (14)O1—C3—H3A109.6
C11—C6—C5121.46 (14)C4—C3—H3A108.8
C7—C6—C5120.55 (14)O1—C3—H3B109.1
C2—O1—C3110.13 (13)C4—C3—H3B109.4
C15—C16—C17119.96 (15)H3A—C3—H3B108.0
C15—C16—H16A120.0O1—C2—C1112.15 (15)
C17—C16—H16A120.0O1—C2—H2A109.7
N1—C18—C17177.55 (18)C1—C2—H2A109.5
C10—C11—C6121.37 (14)O1—C2—H2B108.9
C10—C11—H11A119.4C1—C2—H2B108.6
C6—C11—H11A119.3H2A—C2—H2B107.9
C7—C8—C9121.16 (14)
C6—C5—N2—C475.91 (17)C9—C10—C11—C60.0 (2)
C6—C5—N2—C1−161.33 (14)C7—C6—C11—C100.8 (2)
C10—C9—C12—C13−129.59 (16)C5—C6—C11—C10−177.38 (14)
C8—C9—C12—C1348.3 (2)C6—C7—C8—C90.1 (2)
C10—C9—C12—C1750.1 (2)C10—C9—C8—C70.6 (2)
C8—C9—C12—C17−131.94 (15)C12—C9—C8—C7−177.35 (13)
C13—C12—C17—C161.0 (2)C17—C12—C13—C14−0.4 (2)
C9—C12—C17—C16−178.70 (13)C9—C12—C13—C14179.34 (15)
C13—C12—C17—C18−176.48 (14)C5—N2—C4—C3−175.30 (13)
C9—C12—C17—C183.8 (2)C1—N2—C4—C359.43 (18)
C8—C9—C10—C11−0.7 (2)C12—C13—C14—C15−0.5 (3)
C12—C9—C10—C11177.28 (13)C17—C16—C15—C14−0.3 (2)
C8—C7—C6—C11−0.8 (2)C13—C14—C15—C160.9 (3)
C8—C7—C6—C5177.36 (14)C4—N2—C1—C2−59.12 (19)
N2—C5—C6—C11−147.09 (15)C5—N2—C1—C2176.50 (14)
N2—C5—C6—C734.8 (2)C2—O1—C3—C456.2 (2)
C12—C17—C16—C15−0.7 (2)N2—C4—C3—O1−58.5 (2)
C18—C17—C16—C15176.86 (15)C3—O1—C2—C1−56.5 (2)
C16—C17—C18—N1−39 (4)N2—C1—C2—O158.6 (2)
C12—C17—C18—N1138 (4)

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C6–C11 ring.
D—H···AD—HH···AD···AD—H···A
C1—H1A···Cg2i0.962.763.638 (3)151
C16—H16A···Cg2ii0.932.873.746 (3)157

Symmetry codes: (i) −x+5/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5523).

References

  • Li, X. Z., Qu, Z. R. & Xiong, R. G. (2008). Chin. J. Chem.11, 1959–1962.
  • Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, W., Chen, L. Z., Xiong, R. G., Nakamura, T. & Huang, S. D. (2009). J. Am. Chem. Soc.131, 12544–12545. [PubMed]

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