Crystal structure of 3-(morpholin-4-yl)-1-phenyl-3-(pyridin-2-yl)propan-1-one.

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 inter-actions link the mol-ecules into inversion dimers.

Related literature

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

Crystal data

C18H20N2O2

M = 296.36

Orthorhombic,

a = 12.4554 (6) Å

b = 8.2204 (4) Å

c = 30.6681 (17) Å

V = 3140.1 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.954, T max = 0.975

16093 measured reflections

3812 independent reflections

2547 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.03

3812 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAINT (Bruker, 2008 ▸); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989014026292/hb7328sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026292/hb7328Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014026292/hb7328Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014026292/hb7328fig1.tif

The mol­ecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.

CCDC reference: 1036843

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H20N2O2	F(000) = 1264
Mr = 296.36	Dx = 1.254 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3812 reflections
a = 12.4554 (6) Å	θ = 1.3–28.4°
b = 8.2204 (4) Å	µ = 0.08 mm−1
c = 30.6681 (17) Å	T = 295 K
V = 3140.1 (3) Å3	Block, colourless
Z = 8	0.20 × 0.15 × 0.10 mm

Bruker APEXII CCD diffractometer	3812 independent reflections
Radiation source: fine-focus sealed tube	2547 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 0 pixels mm-1	θmax = 28.4°, θmin = 1.3°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.954, Tmax = 0.975	l = −35→40
16093 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-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 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.42802 (13)	−0.1732 (2)	0.02138 (5)	0.0604 (4)
H1	0.5020	−0.1642	0.0182	0.073*
C2	0.36782 (16)	−0.2413 (2)	−0.01152 (6)	0.0746 (5)
H2	0.4013	−0.2768	−0.0369	0.089*
C3	0.25900 (16)	−0.2571 (2)	−0.00707 (5)	0.0680 (5)
H3	0.2186	−0.3050	−0.0291	0.082*
C4	0.21022 (13)	−0.2020 (2)	0.02998 (6)	0.0653 (5)
H4	0.1362	−0.2121	0.0330	0.078*
C5	0.26935 (12)	−0.13170 (19)	0.06292 (5)	0.0529 (4)
H5	0.2350	−0.0932	0.0878	0.063*
C6	0.37980 (11)	−0.11808 (15)	0.05909 (4)	0.0412 (3)
C7	0.44770 (10)	−0.04735 (16)	0.09421 (4)	0.0417 (3)
C8	0.39381 (10)	0.03707 (17)	0.13181 (4)	0.0429 (3)
H8A	0.3510	−0.0418	0.1477	0.051*
H8B	0.3453	0.1190	0.1204	0.051*
C9	0.47105 (9)	0.11758 (15)	0.16326 (4)	0.0364 (3)
H9	0.5269	0.0372	0.1697	0.044*
C10	0.52724 (10)	0.26260 (15)	0.14299 (4)	0.0368 (3)
C11	0.51464 (16)	0.4990 (2)	0.10454 (6)	0.0666 (5)
H11	0.4726	0.5746	0.0898	0.080*
C12	0.62216 (16)	0.5287 (2)	0.10752 (6)	0.0678 (5)
H12	0.6520	0.6215	0.0951	0.081*
C13	0.68473 (13)	0.4190 (2)	0.12904 (5)	0.0610 (5)
H13	0.7585	0.4344	0.1313	0.073*
C14	0.63651 (11)	0.28526 (18)	0.14735 (5)	0.0452 (3)
H14	0.6775	0.2099	0.1627	0.054*
C15	0.33073 (11)	0.2736 (2)	0.20287 (5)	0.0532 (4)
H15A	0.2787	0.2424	0.1809	0.064*
H15B	0.3602	0.3787	0.1949	0.064*
C16	0.27665 (12)	0.2851 (2)	0.24674 (6)	0.0662 (5)
H16A	0.2195	0.3651	0.2453	0.079*
H16B	0.2447	0.1808	0.2539	0.079*
C17	0.43388 (14)	0.2128 (2)	0.28202 (5)	0.0632 (4)
H17A	0.4040	0.1078	0.2898	0.076*
H17B	0.4846	0.2440	0.3045	0.076*
C18	0.49150 (11)	0.19882 (18)	0.23921 (4)	0.0462 (3)
H18A	0.5247	0.3021	0.2320	0.055*
H18B	0.5477	0.1176	0.2415	0.055*
N1	0.46563 (10)	0.36867 (15)	0.12143 (4)	0.0526 (3)
N2	0.41661 (8)	0.15290 (13)	0.20488 (4)	0.0394 (3)
O1	0.54495 (8)	−0.05833 (15)	0.09246 (4)	0.0655 (3)
O2	0.35010 (10)	0.32957 (14)	0.27995 (4)	0.0678 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0564 (9)	0.0742 (11)	0.0506 (9)	−0.0007 (8)	0.0083 (8)	−0.0126 (8)
C2	0.0842 (13)	0.0925 (14)	0.0470 (10)	−0.0019 (11)	0.0067 (9)	−0.0220 (9)
C3	0.0815 (12)	0.0728 (11)	0.0497 (9)	−0.0123 (10)	−0.0134 (9)	−0.0073 (9)
C4	0.0567 (9)	0.0784 (12)	0.0607 (10)	−0.0166 (9)	−0.0049 (8)	−0.0085 (9)
C5	0.0495 (9)	0.0615 (9)	0.0477 (8)	−0.0098 (7)	0.0030 (7)	−0.0074 (7)
C6	0.0473 (7)	0.0366 (7)	0.0399 (7)	−0.0009 (6)	0.0012 (6)	0.0008 (6)
C7	0.0410 (7)	0.0392 (7)	0.0449 (8)	0.0005 (6)	0.0027 (6)	0.0003 (6)
C8	0.0379 (7)	0.0446 (7)	0.0461 (8)	−0.0049 (6)	0.0040 (6)	−0.0039 (6)
C9	0.0328 (6)	0.0363 (7)	0.0402 (7)	0.0024 (5)	0.0011 (5)	0.0002 (6)
C10	0.0376 (7)	0.0382 (7)	0.0346 (6)	−0.0004 (5)	0.0020 (5)	−0.0025 (5)
C11	0.0910 (13)	0.0498 (9)	0.0589 (10)	−0.0004 (9)	−0.0032 (9)	0.0166 (8)
C12	0.0926 (13)	0.0549 (10)	0.0559 (10)	−0.0279 (10)	0.0183 (9)	0.0017 (8)
C13	0.0555 (9)	0.0663 (10)	0.0613 (10)	−0.0229 (8)	0.0155 (8)	−0.0162 (9)
C14	0.0389 (7)	0.0512 (8)	0.0456 (8)	−0.0027 (6)	0.0030 (6)	−0.0067 (7)
C15	0.0404 (7)	0.0569 (9)	0.0624 (10)	0.0062 (7)	0.0048 (7)	−0.0090 (8)
C16	0.0500 (9)	0.0641 (10)	0.0844 (12)	−0.0057 (8)	0.0237 (9)	−0.0198 (9)
C17	0.0810 (11)	0.0612 (10)	0.0473 (9)	−0.0109 (9)	0.0080 (8)	−0.0065 (8)
C18	0.0483 (8)	0.0451 (8)	0.0453 (8)	−0.0029 (7)	−0.0002 (6)	−0.0014 (6)
N1	0.0530 (7)	0.0496 (7)	0.0553 (7)	0.0018 (6)	−0.0067 (6)	0.0125 (6)
N2	0.0355 (5)	0.0409 (6)	0.0419 (6)	−0.0012 (5)	0.0040 (5)	−0.0024 (5)
O1	0.0412 (6)	0.0847 (9)	0.0707 (8)	0.0064 (5)	0.0016 (5)	−0.0247 (6)
O2	0.0733 (7)	0.0648 (7)	0.0654 (7)	−0.0114 (6)	0.0215 (6)	−0.0235 (6)

C1—C2	1.376 (2)	C11—N1	1.338 (2)
C1—C6	1.380 (2)	C11—C12	1.364 (3)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.368 (3)	C12—C13	1.362 (2)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.366 (2)	C13—C14	1.373 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.377 (2)	C14—H14	0.9300
C4—H4	0.9300	C15—N2	1.4604 (17)
C5—C6	1.3852 (19)	C15—C16	1.508 (2)
C5—H5	0.9300	C15—H15A	0.9700
C6—C7	1.4878 (19)	C15—H15B	0.9700
C7—O1	1.2159 (15)	C16—O2	1.417 (2)
C7—C8	1.5039 (19)	C16—H16A	0.9700
C8—C9	1.5146 (18)	C16—H16B	0.9700
C8—H8A	0.9700	C17—O2	1.419 (2)
C8—H8B	0.9700	C17—C18	1.500 (2)
C9—N2	1.4741 (16)	C17—H17A	0.9700
C9—C10	1.5157 (18)	C17—H17B	0.9700
C9—H9	0.9800	C18—N2	1.4565 (17)
C10—N1	1.3365 (17)	C18—H18A	0.9700
C10—C14	1.3803 (17)	C18—H18B	0.9700
C2—C1—C6	120.73 (15)	C13—C12—C11	118.42 (15)
C2—C1—H1	119.6	C13—C12—H12	120.8
C6—C1—H1	119.6	C11—C12—H12	120.8
C3—C2—C1	120.36 (16)	C12—C13—C14	118.55 (15)
C3—C2—H2	119.8	C12—C13—H13	120.7
C1—C2—H2	119.8	C14—C13—H13	120.7
C4—C3—C2	119.47 (16)	C13—C14—C10	119.99 (15)
C4—C3—H3	120.3	C13—C14—H14	120.0
C2—C3—H3	120.3	C10—C14—H14	120.0
C3—C4—C5	120.76 (15)	N2—C15—C16	109.39 (13)
C3—C4—H4	119.6	N2—C15—H15A	109.8
C5—C4—H4	119.6	C16—C15—H15A	109.8
C4—C5—C6	120.18 (14)	N2—C15—H15B	109.8
C4—C5—H5	119.9	C16—C15—H15B	109.8
C6—C5—H5	119.9	H15A—C15—H15B	108.2
C1—C6—C5	118.48 (13)	O2—C16—C15	111.65 (12)
C1—C6—C7	119.19 (12)	O2—C16—H16A	109.3
C5—C6—C7	122.33 (12)	C15—C16—H16A	109.3
O1—C7—C6	120.35 (13)	O2—C16—H16B	109.3
O1—C7—C8	120.85 (12)	C15—C16—H16B	109.3
C6—C7—C8	118.80 (11)	H16A—C16—H16B	108.0
C7—C8—C9	113.98 (10)	O2—C17—C18	111.37 (13)
C7—C8—H8A	108.8	O2—C17—H17A	109.4
C9—C8—H8A	108.8	C18—C17—H17A	109.4
C7—C8—H8B	108.8	O2—C17—H17B	109.4
C9—C8—H8B	108.8	C18—C17—H17B	109.4
H8A—C8—H8B	107.7	H17A—C17—H17B	108.0
N2—C9—C8	110.20 (10)	N2—C18—C17	110.24 (12)
N2—C9—C10	114.37 (10)	N2—C18—H18A	109.6
C8—C9—C10	112.07 (11)	C17—C18—H18A	109.6
N2—C9—H9	106.6	N2—C18—H18B	109.6
C8—C9—H9	106.6	C17—C18—H18B	109.6
C10—C9—H9	106.6	H18A—C18—H18B	108.1
N1—C10—C14	121.74 (13)	C10—N1—C11	116.89 (13)
N1—C10—C9	116.80 (11)	C18—N2—C15	108.87 (11)
C14—C10—C9	121.45 (12)	C18—N2—C9	112.48 (10)
N1—C11—C12	124.40 (17)	C15—N2—C9	115.74 (11)
N1—C11—H11	117.8	C16—O2—C17	109.40 (12)
C12—C11—H11	117.8
C6—C1—C2—C3	−0.8 (3)	N1—C11—C12—C13	0.0 (3)
C1—C2—C3—C4	1.2 (3)	C11—C12—C13—C14	−1.1 (2)
C2—C3—C4—C5	−0.3 (3)	C12—C13—C14—C10	1.3 (2)
C3—C4—C5—C6	−0.9 (3)	N1—C10—C14—C13	−0.4 (2)
C2—C1—C6—C5	−0.5 (2)	C9—C10—C14—C13	−179.19 (13)
C2—C1—C6—C7	179.11 (16)	N2—C15—C16—O2	59.10 (17)
C4—C5—C6—C1	1.3 (2)	O2—C17—C18—N2	−58.71 (16)
C4—C5—C6—C7	−178.26 (14)	C14—C10—N1—C11	−0.6 (2)
C1—C6—C7—O1	−10.1 (2)	C9—C10—N1—C11	178.23 (13)
C5—C6—C7—O1	169.48 (15)	C12—C11—N1—C10	0.8 (3)
C1—C6—C7—C8	170.08 (13)	C17—C18—N2—C15	57.48 (15)
C5—C6—C7—C8	−10.3 (2)	C17—C18—N2—C9	−172.87 (12)
O1—C7—C8—C9	5.6 (2)	C16—C15—N2—C18	−57.27 (15)
C6—C7—C8—C9	−174.59 (11)	C16—C15—N2—C9	174.89 (11)
C7—C8—C9—N2	−162.92 (11)	C8—C9—N2—C18	168.06 (11)
C7—C8—C9—C10	68.50 (15)	C10—C9—N2—C18	−64.62 (14)
N2—C9—C10—N1	−79.35 (15)	C8—C9—N2—C15	−65.92 (14)
C8—C9—C10—N1	47.00 (15)	C10—C9—N2—C15	61.40 (14)
N2—C9—C10—C14	99.47 (14)	C15—C16—O2—C17	−58.86 (18)
C8—C9—C10—C14	−134.18 (13)	C18—C17—O2—C16	58.37 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg2i	0.93	2.90	3.780 (6)	159

Table 1

Hydrogen-bond geometry (, )

Cg2 is the centroid of the C10C14/N1 ring.

DHA	DH	HA	D A	DHA
C2H2Cg2i	0.93	2.90	3.780(6)	159

Symmetry code: (i) .