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In the title compound C18H20N2O2, the morpholine ring adopts a chair conformation with the exocyclic N—C bond in an equatorial orientation. The N atom of the morpholine ring and the C atom of the carbonyl group are in an anti conformation about the central C—C bond [torsion angle = −162.92 (11)°] and the dihedral angle between the planes of the benzene ring and the pyridine ring is 83.30 (5)°. In the crystal, pairs of very weak C—H...π inter­actions link the mol­ecules into inversion dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989014026292/hb7328sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989014026292/hb7328Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989014026292/hb7328Isup3.cml
Supplementary material

CCDC reference: 1036843

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.111
  • Data-to-parameter ratio = 19.2

checkCIF/PLATON results

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Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.970 Note
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT793_ALERT_4_G The Model has Chirality at C9 ............. S Verify PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 88 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Morpholines are six-membered heterocycles featuring both cyclic amine and ether functional group. These compounds possess important applications in pharmaceuticals and in industries (Panneerselvam et al., 2009; Subhashini et al., 2013). Chiral morpholine derivatives have found numerous applications in asymmetric synthesis as chiral auxiliaries as well as chiral ligands (Sawant et al., 2013; Dave & Sasaki 2006).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Chen et al., 2011; Meti et al., 2013). The morpholine (N2/O2/C15—C18)ring adopts a chair conformation [Q = 0.5756 (3) Å, Θ = 179.09 (3)°, φ = 332.57 (5)°]. The phenyl ring makes a dihedral angles of 83.30 (5) ° with the pyridine ring. In the crystal, a weak C—H···π interaction is observed.

Related literature top

For background to the biological activity of morpholine derivatives, see: Panneerselvam et al. (2009); Subhashini et al. (2013); Sawant et al. (2013); Dave & Sasaki (2006); For related structures, see: Chen et al. (2011); Meti et al. (2013);

Experimental top

To an ethanolic solution of acetophenone (3.0 ml, 0.025 mol) taken in a round bottom flask, morpholine (2.1 ml, 0.025 mol) and pyridine-2-carboldehyde (2.6 ml, 0.025 mol) were added. The reaction mixture was kept over a magnetic stirrer and stirred well in an ice cold condition for 3 hr. The colourless solid formed was filtered and washed several times with petroleum ether (40–60%). The crude solid obtained was dried and recrystallized using absolute alcohol. The recrystallized product was dried over vacuum. The yield is 78% and MP is 445 K.

Refinement top

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for C—H2,

Structure description top

Morpholines are six-membered heterocycles featuring both cyclic amine and ether functional group. These compounds possess important applications in pharmaceuticals and in industries (Panneerselvam et al., 2009; Subhashini et al., 2013). Chiral morpholine derivatives have found numerous applications in asymmetric synthesis as chiral auxiliaries as well as chiral ligands (Sawant et al., 2013; Dave & Sasaki 2006).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Chen et al., 2011; Meti et al., 2013). The morpholine (N2/O2/C15—C18)ring adopts a chair conformation [Q = 0.5756 (3) Å, Θ = 179.09 (3)°, φ = 332.57 (5)°]. The phenyl ring makes a dihedral angles of 83.30 (5) ° with the pyridine ring. In the crystal, a weak C—H···π interaction is observed.

For background to the biological activity of morpholine derivatives, see: Panneerselvam et al. (2009); Subhashini et al. (2013); Sawant et al. (2013); Dave & Sasaki (2006); For related structures, see: Chen et al. (2011); Meti et al. (2013);

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.
3-(Morpholin-4-yl)-1-phenyl-3-(pyridin-2-yl)propan-1-one top
Crystal data top
C18H20N2O2F(000) = 1264
Mr = 296.36Dx = 1.254 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3812 reflections
a = 12.4554 (6) Åθ = 1.3–28.4°
b = 8.2204 (4) ŵ = 0.08 mm1
c = 30.6681 (17) ÅT = 295 K
V = 3140.1 (3) Å3Block, colourless
Z = 80.20 × 0.15 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
3812 independent reflections
Radiation source: fine-focus sealed tube2547 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 0 pixels mm-1θmax = 28.4°, θmin = 1.3°
ω and φ scansh = 1515
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1010
Tmin = 0.954, Tmax = 0.975l = 3540
16093 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0416P)2 + 0.6298P]
where P = (Fo2 + 2Fc2)/3
3812 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C18H20N2O2V = 3140.1 (3) Å3
Mr = 296.36Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.4554 (6) ŵ = 0.08 mm1
b = 8.2204 (4) ÅT = 295 K
c = 30.6681 (17) Å0.20 × 0.15 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
3812 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2547 reflections with I > 2σ(I)
Tmin = 0.954, Tmax = 0.975Rint = 0.028
16093 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.03Δρmax = 0.14 e Å3
3812 reflectionsΔρmin = 0.16 e Å3
199 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.42802 (13)0.1732 (2)0.02138 (5)0.0604 (4)
H10.50200.16420.01820.073*
C20.36782 (16)0.2413 (2)0.01152 (6)0.0746 (5)
H20.40130.27680.03690.089*
C30.25900 (16)0.2571 (2)0.00707 (5)0.0680 (5)
H30.21860.30500.02910.082*
C40.21022 (13)0.2020 (2)0.02998 (6)0.0653 (5)
H40.13620.21210.03300.078*
C50.26935 (12)0.13170 (19)0.06292 (5)0.0529 (4)
H50.23500.09320.08780.063*
C60.37980 (11)0.11808 (15)0.05909 (4)0.0412 (3)
C70.44770 (10)0.04735 (16)0.09421 (4)0.0417 (3)
C80.39381 (10)0.03707 (17)0.13181 (4)0.0429 (3)
H8A0.35100.04180.14770.051*
H8B0.34530.11900.12040.051*
C90.47105 (9)0.11758 (15)0.16326 (4)0.0364 (3)
H90.52690.03720.16970.044*
C100.52724 (10)0.26260 (15)0.14299 (4)0.0368 (3)
C110.51464 (16)0.4990 (2)0.10454 (6)0.0666 (5)
H110.47260.57460.08980.080*
C120.62216 (16)0.5287 (2)0.10752 (6)0.0678 (5)
H120.65200.62150.09510.081*
C130.68473 (13)0.4190 (2)0.12904 (5)0.0610 (5)
H130.75850.43440.13130.073*
C140.63651 (11)0.28526 (18)0.14735 (5)0.0452 (3)
H140.67750.20990.16270.054*
C150.33073 (11)0.2736 (2)0.20287 (5)0.0532 (4)
H15A0.27870.24240.18090.064*
H15B0.36020.37870.19490.064*
C160.27665 (12)0.2851 (2)0.24674 (6)0.0662 (5)
H16A0.21950.36510.24530.079*
H16B0.24470.18080.25390.079*
C170.43388 (14)0.2128 (2)0.28202 (5)0.0632 (4)
H17A0.40400.10780.28980.076*
H17B0.48460.24400.30450.076*
C180.49150 (11)0.19882 (18)0.23921 (4)0.0462 (3)
H18A0.52470.30210.23200.055*
H18B0.54770.11760.24150.055*
N10.46563 (10)0.36867 (15)0.12143 (4)0.0526 (3)
N20.41661 (8)0.15290 (13)0.20488 (4)0.0394 (3)
O10.54495 (8)0.05833 (15)0.09246 (4)0.0655 (3)
O20.35010 (10)0.32957 (14)0.27995 (4)0.0678 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0564 (9)0.0742 (11)0.0506 (9)0.0007 (8)0.0083 (8)0.0126 (8)
C20.0842 (13)0.0925 (14)0.0470 (10)0.0019 (11)0.0067 (9)0.0220 (9)
C30.0815 (12)0.0728 (11)0.0497 (9)0.0123 (10)0.0134 (9)0.0073 (9)
C40.0567 (9)0.0784 (12)0.0607 (10)0.0166 (9)0.0049 (8)0.0085 (9)
C50.0495 (9)0.0615 (9)0.0477 (8)0.0098 (7)0.0030 (7)0.0074 (7)
C60.0473 (7)0.0366 (7)0.0399 (7)0.0009 (6)0.0012 (6)0.0008 (6)
C70.0410 (7)0.0392 (7)0.0449 (8)0.0005 (6)0.0027 (6)0.0003 (6)
C80.0379 (7)0.0446 (7)0.0461 (8)0.0049 (6)0.0040 (6)0.0039 (6)
C90.0328 (6)0.0363 (7)0.0402 (7)0.0024 (5)0.0011 (5)0.0002 (6)
C100.0376 (7)0.0382 (7)0.0346 (6)0.0004 (5)0.0020 (5)0.0025 (5)
C110.0910 (13)0.0498 (9)0.0589 (10)0.0004 (9)0.0032 (9)0.0166 (8)
C120.0926 (13)0.0549 (10)0.0559 (10)0.0279 (10)0.0183 (9)0.0017 (8)
C130.0555 (9)0.0663 (10)0.0613 (10)0.0229 (8)0.0155 (8)0.0162 (9)
C140.0389 (7)0.0512 (8)0.0456 (8)0.0027 (6)0.0030 (6)0.0067 (7)
C150.0404 (7)0.0569 (9)0.0624 (10)0.0062 (7)0.0048 (7)0.0090 (8)
C160.0500 (9)0.0641 (10)0.0844 (12)0.0057 (8)0.0237 (9)0.0198 (9)
C170.0810 (11)0.0612 (10)0.0473 (9)0.0109 (9)0.0080 (8)0.0065 (8)
C180.0483 (8)0.0451 (8)0.0453 (8)0.0029 (7)0.0002 (6)0.0014 (6)
N10.0530 (7)0.0496 (7)0.0553 (7)0.0018 (6)0.0067 (6)0.0125 (6)
N20.0355 (5)0.0409 (6)0.0419 (6)0.0012 (5)0.0040 (5)0.0024 (5)
O10.0412 (6)0.0847 (9)0.0707 (8)0.0064 (5)0.0016 (5)0.0247 (6)
O20.0733 (7)0.0648 (7)0.0654 (7)0.0114 (6)0.0215 (6)0.0235 (6)
Geometric parameters (Å, º) top
C1—C21.376 (2)C11—N11.338 (2)
C1—C61.380 (2)C11—C121.364 (3)
C1—H10.9300C11—H110.9300
C2—C31.368 (3)C12—C131.362 (2)
C2—H20.9300C12—H120.9300
C3—C41.366 (2)C13—C141.373 (2)
C3—H30.9300C13—H130.9300
C4—C51.377 (2)C14—H140.9300
C4—H40.9300C15—N21.4604 (17)
C5—C61.3852 (19)C15—C161.508 (2)
C5—H50.9300C15—H15A0.9700
C6—C71.4878 (19)C15—H15B0.9700
C7—O11.2159 (15)C16—O21.417 (2)
C7—C81.5039 (19)C16—H16A0.9700
C8—C91.5146 (18)C16—H16B0.9700
C8—H8A0.9700C17—O21.419 (2)
C8—H8B0.9700C17—C181.500 (2)
C9—N21.4741 (16)C17—H17A0.9700
C9—C101.5157 (18)C17—H17B0.9700
C9—H90.9800C18—N21.4565 (17)
C10—N11.3365 (17)C18—H18A0.9700
C10—C141.3803 (17)C18—H18B0.9700
C2—C1—C6120.73 (15)C13—C12—C11118.42 (15)
C2—C1—H1119.6C13—C12—H12120.8
C6—C1—H1119.6C11—C12—H12120.8
C3—C2—C1120.36 (16)C12—C13—C14118.55 (15)
C3—C2—H2119.8C12—C13—H13120.7
C1—C2—H2119.8C14—C13—H13120.7
C4—C3—C2119.47 (16)C13—C14—C10119.99 (15)
C4—C3—H3120.3C13—C14—H14120.0
C2—C3—H3120.3C10—C14—H14120.0
C3—C4—C5120.76 (15)N2—C15—C16109.39 (13)
C3—C4—H4119.6N2—C15—H15A109.8
C5—C4—H4119.6C16—C15—H15A109.8
C4—C5—C6120.18 (14)N2—C15—H15B109.8
C4—C5—H5119.9C16—C15—H15B109.8
C6—C5—H5119.9H15A—C15—H15B108.2
C1—C6—C5118.48 (13)O2—C16—C15111.65 (12)
C1—C6—C7119.19 (12)O2—C16—H16A109.3
C5—C6—C7122.33 (12)C15—C16—H16A109.3
O1—C7—C6120.35 (13)O2—C16—H16B109.3
O1—C7—C8120.85 (12)C15—C16—H16B109.3
C6—C7—C8118.80 (11)H16A—C16—H16B108.0
C7—C8—C9113.98 (10)O2—C17—C18111.37 (13)
C7—C8—H8A108.8O2—C17—H17A109.4
C9—C8—H8A108.8C18—C17—H17A109.4
C7—C8—H8B108.8O2—C17—H17B109.4
C9—C8—H8B108.8C18—C17—H17B109.4
H8A—C8—H8B107.7H17A—C17—H17B108.0
N2—C9—C8110.20 (10)N2—C18—C17110.24 (12)
N2—C9—C10114.37 (10)N2—C18—H18A109.6
C8—C9—C10112.07 (11)C17—C18—H18A109.6
N2—C9—H9106.6N2—C18—H18B109.6
C8—C9—H9106.6C17—C18—H18B109.6
C10—C9—H9106.6H18A—C18—H18B108.1
N1—C10—C14121.74 (13)C10—N1—C11116.89 (13)
N1—C10—C9116.80 (11)C18—N2—C15108.87 (11)
C14—C10—C9121.45 (12)C18—N2—C9112.48 (10)
N1—C11—C12124.40 (17)C15—N2—C9115.74 (11)
N1—C11—H11117.8C16—O2—C17109.40 (12)
C12—C11—H11117.8
C6—C1—C2—C30.8 (3)N1—C11—C12—C130.0 (3)
C1—C2—C3—C41.2 (3)C11—C12—C13—C141.1 (2)
C2—C3—C4—C50.3 (3)C12—C13—C14—C101.3 (2)
C3—C4—C5—C60.9 (3)N1—C10—C14—C130.4 (2)
C2—C1—C6—C50.5 (2)C9—C10—C14—C13179.19 (13)
C2—C1—C6—C7179.11 (16)N2—C15—C16—O259.10 (17)
C4—C5—C6—C11.3 (2)O2—C17—C18—N258.71 (16)
C4—C5—C6—C7178.26 (14)C14—C10—N1—C110.6 (2)
C1—C6—C7—O110.1 (2)C9—C10—N1—C11178.23 (13)
C5—C6—C7—O1169.48 (15)C12—C11—N1—C100.8 (3)
C1—C6—C7—C8170.08 (13)C17—C18—N2—C1557.48 (15)
C5—C6—C7—C810.3 (2)C17—C18—N2—C9172.87 (12)
O1—C7—C8—C95.6 (2)C16—C15—N2—C1857.27 (15)
C6—C7—C8—C9174.59 (11)C16—C15—N2—C9174.89 (11)
C7—C8—C9—N2162.92 (11)C8—C9—N2—C18168.06 (11)
C7—C8—C9—C1068.50 (15)C10—C9—N2—C1864.62 (14)
N2—C9—C10—N179.35 (15)C8—C9—N2—C1565.92 (14)
C8—C9—C10—N147.00 (15)C10—C9—N2—C1561.40 (14)
N2—C9—C10—C1499.47 (14)C15—C16—O2—C1758.86 (18)
C8—C9—C10—C14134.18 (13)C18—C17—O2—C1658.37 (16)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C10–C14/N1 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···Cg2i0.932.903.780 (6)159
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C10–C14/N1 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···Cg2i0.932.903.780 (6)159
Symmetry code: (i) x, y+1, z.
 

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