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In the title compound, C9H14N2O3, the morpholine ring adopts the usual chair conformation. The pyrrolidine-2,5-dione ring adopts an extremely flattened envelope conformation. The crystal structure is stabilized by weak C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046053/bt2514sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046053/bt2514Isup2.hkl
Contains datablock I

CCDC reference: 660711

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.033
  • wR factor = 0.089
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O3 .. C1 .. 2.91 Ang.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Morpholine is a multipurpose chemical which is used as a solvent for resins, dyes and waxes. One of its most important uses is as a chemical intermediate in the preparation of pesticides (Li et al., 1998). Drugs containing a morpholine ring have established activities that include the reduction of blood sugar and lipid levels (Yoshioka, 1995), and amelioration of obesity and insulin resistance (Fisher & Wyvratt, 1990). Owing to their pharmcological activities these compounds have received a great deal of attention in respect of their synthesis and conformation. A group of phenylsuccinimides (Lucka-Sobstel Zejc & Obniska 1977; Zejc & Obniska, 1984) proved to have strong anticonvulsive activity.

A perspective view of the title compound is shown in Fig. 1. In the morpholine ring, the average C—N, C—C and C—O bond distances [1.453 (2), 1.497 (2) and 1.417 (2) A°, respectively] are in good agreement with earlier reports (Ramnathan et al., 1996). The morpholine ring adopts the usual chair conformation. This is in agreement with the structural data available from Version 5.14 of the Cambridge Structural Database (Allen, 2002). The pyrrolidine-2,5-dione or succinimide ring adopts an extremely flattened envelope conformation with atom C1 deviating by 0.025 A° from the mean plane through the remaining atoms in the ring. The sum of the angles around N1 is 358.70 (13)° indicating sp2 hybridization. However the N1—C1 [1.3870 (2) Å and N1—C4 [1.375 (19) Å] distances are intermediate between the average Car –Nsp3(pyramidal) [1.419 (17) Å] and Car—Nsp2(planar) [1.353 (7) Å] distances reported by Allen et al. (1987). The dihedral angle between the planes of the morpholine and pyrrolidine-2,5-dione ring is 63.26 (7)°. Weak intermolecular C—H···O (Fig 2) interactions stabilize the crystal packing.

Related literature top

For related literature, see: Allen (2002); Allen et al. (1987); Fisher & Wyvratt (1990); Li et al. (1998); Lucka-Sobstel et al. (1977); Ramnathan et al. (1996); Yoshioka (1995); Zejc & Obniska (1984).

Experimental top

The title compound was synthesized by condensing morpholine, formaldehyde and succinimide. Then, 9.9 g (0.1M) of succinimide was stirred with 8.1 g of 37% acqueous formaldehyde until the solid succinimide had dissolved. Morpholine (8.0 ml, 0.1M) was added in small quantities and stirred well. The mixture turned oily and was allowed to stand at room temperature for about 12 h. The colorless crystalline product was sepearated by filtration. The crude product was recrystallized from a mixture of ethanol and acetone. Melting point 98°C.

Structure description top

Morpholine is a multipurpose chemical which is used as a solvent for resins, dyes and waxes. One of its most important uses is as a chemical intermediate in the preparation of pesticides (Li et al., 1998). Drugs containing a morpholine ring have established activities that include the reduction of blood sugar and lipid levels (Yoshioka, 1995), and amelioration of obesity and insulin resistance (Fisher & Wyvratt, 1990). Owing to their pharmcological activities these compounds have received a great deal of attention in respect of their synthesis and conformation. A group of phenylsuccinimides (Lucka-Sobstel Zejc & Obniska 1977; Zejc & Obniska, 1984) proved to have strong anticonvulsive activity.

A perspective view of the title compound is shown in Fig. 1. In the morpholine ring, the average C—N, C—C and C—O bond distances [1.453 (2), 1.497 (2) and 1.417 (2) A°, respectively] are in good agreement with earlier reports (Ramnathan et al., 1996). The morpholine ring adopts the usual chair conformation. This is in agreement with the structural data available from Version 5.14 of the Cambridge Structural Database (Allen, 2002). The pyrrolidine-2,5-dione or succinimide ring adopts an extremely flattened envelope conformation with atom C1 deviating by 0.025 A° from the mean plane through the remaining atoms in the ring. The sum of the angles around N1 is 358.70 (13)° indicating sp2 hybridization. However the N1—C1 [1.3870 (2) Å and N1—C4 [1.375 (19) Å] distances are intermediate between the average Car –Nsp3(pyramidal) [1.419 (17) Å] and Car—Nsp2(planar) [1.353 (7) Å] distances reported by Allen et al. (1987). The dihedral angle between the planes of the morpholine and pyrrolidine-2,5-dione ring is 63.26 (7)°. Weak intermolecular C—H···O (Fig 2) interactions stabilize the crystal packing.

For related literature, see: Allen (2002); Allen et al. (1987); Fisher & Wyvratt (1990); Li et al. (1998); Lucka-Sobstel et al. (1977); Ramnathan et al. (1996); Yoshioka (1995); Zejc & Obniska (1984).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing the atom numbering scheme with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound. C—H···O interactions are drawn as dashed lines.
1-(Morpholin-4-ylmethyl)pyrrolidine-2,5-dione top
Crystal data top
C9H14N2O3F(000) = 424
Mr = 198.22Dx = 1.329 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2548 reflections
a = 6.1368 (2) Åθ = 2.0–23.7°
b = 7.8038 (3) ŵ = 0.10 mm1
c = 20.9032 (8) ÅT = 293 K
β = 98.202 (2)°Prism, colourless
V = 990.82 (6) Å30.26 × 0.18 × 0.18 mm
Z = 4
Data collection top
Bruker Kappa-APEX2
diffractometer
1726 independent reflections
Radiation source: fine focus sealed tube1184 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω and φ scansθmax = 25°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 66
Tmin = 0.974, Tmax = 0.982k = 68
8190 measured reflectionsl = 2323
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0448P)2 + 0.1664P]
where P = (Fo2 + 2Fc2)/3
1726 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.13 e Å3
Crystal data top
C9H14N2O3V = 990.82 (6) Å3
Mr = 198.22Z = 4
Monoclinic, P21/nMo Kα radiation
a = 6.1368 (2) ŵ = 0.10 mm1
b = 7.8038 (3) ÅT = 293 K
c = 20.9032 (8) Å0.26 × 0.18 × 0.18 mm
β = 98.202 (2)°
Data collection top
Bruker Kappa-APEX2
diffractometer
1726 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
1184 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.982Rint = 0.026
8190 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.089H-atom parameters constrained
S = 1.02Δρmax = 0.12 e Å3
1726 reflectionsΔρmin = 0.13 e Å3
127 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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*/Ueq
O10.0573 (2)0.26782 (18)0.07851 (6)0.0734 (5)
O20.6854 (2)0.35020 (16)0.21769 (5)0.0655 (5)
O30.4045 (2)0.94347 (16)0.10318 (6)0.0763 (5)
N10.3883 (2)0.33660 (15)0.13812 (5)0.0409 (4)
N20.4843 (2)0.59584 (16)0.07942 (5)0.0417 (4)
C10.1818 (3)0.2607 (2)0.12828 (8)0.0517 (6)
C20.1444 (3)0.1732 (3)0.18956 (9)0.0658 (7)
C30.3581 (3)0.1936 (2)0.23465 (8)0.0621 (7)
C40.5006 (3)0.3011 (2)0.19838 (7)0.0467 (6)
C50.4923 (3)0.4132 (2)0.08505 (7)0.0465 (6)
C60.2643 (3)0.6669 (2)0.06615 (7)0.0487 (6)
C70.2771 (3)0.8541 (2)0.05144 (9)0.0636 (7)
C80.6188 (3)0.8747 (3)0.11511 (10)0.0714 (8)
C90.6152 (3)0.6885 (2)0.13172 (7)0.0514 (6)
H2A0.110230.052940.181810.0790*
H2B0.023980.226640.207570.0790*
H3A0.333330.250000.274340.0746*
H3B0.425670.082940.245260.0746*
H5A0.645550.378330.090610.0558*
H5B0.422120.364750.044550.0558*
H6A0.188370.650660.103350.0585*
H6B0.181650.608000.029620.0585*
H7A0.342810.869150.012280.0762*
H7B0.129650.901760.044020.0762*
H8A0.703610.936590.150480.0857*
H8B0.690630.889660.077040.0857*
H9A0.764140.643760.138440.0616*
H9B0.552460.673300.171390.0616*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0646 (9)0.0780 (10)0.0687 (8)0.0037 (7)0.0209 (7)0.0066 (7)
O20.0579 (9)0.0811 (10)0.0524 (7)0.0013 (7)0.0095 (6)0.0102 (6)
O30.0862 (10)0.0493 (8)0.0854 (9)0.0096 (7)0.0156 (7)0.0157 (6)
N10.0463 (8)0.0413 (8)0.0339 (6)0.0048 (6)0.0012 (5)0.0019 (5)
N20.0479 (8)0.0437 (8)0.0327 (6)0.0038 (6)0.0032 (5)0.0010 (5)
C10.0504 (10)0.0460 (11)0.0562 (10)0.0050 (8)0.0013 (8)0.0005 (8)
C20.0614 (12)0.0686 (13)0.0694 (11)0.0025 (9)0.0158 (9)0.0113 (9)
C30.0763 (13)0.0628 (12)0.0479 (10)0.0004 (9)0.0110 (9)0.0119 (8)
C40.0515 (11)0.0473 (10)0.0395 (8)0.0094 (8)0.0000 (7)0.0010 (7)
C50.0575 (10)0.0492 (11)0.0335 (8)0.0083 (8)0.0089 (7)0.0018 (7)
C60.0508 (10)0.0512 (11)0.0407 (8)0.0037 (8)0.0053 (7)0.0007 (7)
C70.0703 (13)0.0510 (12)0.0633 (11)0.0097 (9)0.0113 (9)0.0007 (8)
C80.0716 (14)0.0591 (13)0.0773 (13)0.0117 (10)0.0110 (10)0.0001 (10)
C90.0464 (10)0.0577 (11)0.0474 (9)0.0021 (8)0.0022 (7)0.0008 (8)
Geometric parameters (Å, º) top
O1—C11.201 (2)C2—H2A0.9700
O2—C41.211 (2)C2—H2B0.9700
O3—C71.423 (2)C3—H3A0.9700
O3—C81.409 (2)C3—H3B0.9700
N1—C11.387 (2)C5—H5A0.9700
N1—C41.3750 (19)C5—H5B0.9700
N1—C51.4823 (19)C6—H6A0.9700
N2—C51.430 (2)C6—H6B0.9700
N2—C61.449 (2)C7—H7A0.9700
N2—C91.4535 (19)C7—H7B0.9700
C1—C21.498 (3)C8—H8A0.9700
C2—C31.510 (3)C8—H8B0.9700
C3—C41.494 (2)C9—H9A0.9700
C6—C71.497 (2)C9—H9B0.9700
C8—C91.495 (3)
O1···C63.387 (2)C6···O1i3.405 (2)
O1···C7i3.302 (2)C6···O13.387 (2)
O1···C6i3.405 (2)C7···O1i3.302 (2)
O2···C93.1881 (19)C9···O23.1881 (19)
O2···C2ii3.265 (2)C9···C43.443 (2)
O3···C3iii3.416 (2)C1···H6A3.0900
O3···C1iii2.911 (2)C4···H9B2.9800
O3···C2iii3.138 (2)H2A···O3vi2.7500
O3···N22.8134 (18)H2A···H3Aviii2.5400
O3···N1iii3.1585 (17)H2B···O2iv2.3300
O1···H5Aiv2.7200H3A···H2Aix2.5400
O1···H6Bi2.6900H5A···O1ii2.7200
O1···H5B2.5600H5A···O22.6400
O2···H8Av2.8200H5A···H9A2.3700
O2···H9B2.7800H5B···O12.5600
O2···H2Bii2.3300H5B···H6B2.4000
O2···H5A2.6400H5B···N2vii2.7500
O2···H9A2.9100H6A···N12.7900
O3···H2Aiii2.7500H6A···C13.0900
N1···O3vi3.1585 (17)H6A···H9B2.4800
N2···O32.8134 (18)H6B···H5B2.4000
N1···H6A2.7900H6B···O1i2.6900
N1···H9B2.8600H7A···H8B2.3600
N2···H5Bvii2.7500H8A···O2x2.8200
C1···O3vi2.911 (2)H8B···H7A2.3600
C1···C63.490 (2)H9A···O22.9100
C2···O2iv3.265 (2)H9A···H5A2.3700
C2···O3vi3.138 (2)H9B···O22.7800
C3···O3vi3.416 (2)H9B···N12.8600
C4···C93.443 (2)H9B···C42.9800
C6···C13.490 (2)H9B···H6A2.4800
C7—O3—C8110.21 (14)C4—C3—H3B111.00
C1—N1—C4112.19 (13)H3A—C3—H3B109.00
C1—N1—C5122.88 (12)N1—C5—H5A108.00
C4—N1—C5123.63 (13)N1—C5—H5B108.00
C5—N2—C6114.65 (13)N2—C5—H5A108.00
C5—N2—C9115.15 (12)N2—C5—H5B108.00
C6—N2—C9110.70 (12)H5A—C5—H5B107.00
O1—C1—N1124.29 (15)N2—C6—H6A110.00
O1—C1—C2127.28 (17)N2—C6—H6B110.00
N1—C1—C2108.42 (14)C7—C6—H6A110.00
C1—C2—C3105.09 (15)C7—C6—H6B110.00
C2—C3—C4105.16 (14)H6A—C6—H6B108.00
O2—C4—N1124.40 (15)O3—C7—H7A109.00
O2—C4—C3126.64 (14)O3—C7—H7B109.00
N1—C4—C3108.96 (14)C6—C7—H7A109.00
N1—C5—N2116.74 (13)C6—C7—H7B109.00
N2—C6—C7109.75 (14)H7A—C7—H7B108.00
O3—C7—C6111.18 (14)O3—C8—H8A109.00
O3—C8—C9111.53 (16)O3—C8—H8B109.00
N2—C9—C8109.50 (13)C9—C8—H8A109.00
C1—C2—H2A111.00C9—C8—H8B109.00
C1—C2—H2B111.00H8A—C8—H8B108.00
C3—C2—H2A111.00N2—C9—H9A110.00
C3—C2—H2B111.00N2—C9—H9B110.00
H2A—C2—H2B109.00C8—C9—H9A110.00
C2—C3—H3A111.00C8—C9—H9B110.00
C2—C3—H3B111.00H9A—C9—H9B108.00
C4—C3—H3A111.00
C7—O3—C8—C958.88 (19)C9—N2—C6—C756.19 (16)
C8—O3—C7—C658.47 (19)C5—N2—C6—C7171.49 (12)
C5—N1—C1—O19.5 (2)C6—N2—C5—N162.17 (16)
C4—N1—C1—O1176.91 (16)C9—N2—C5—N168.00 (18)
C1—N1—C4—C31.31 (18)C6—N2—C9—C856.24 (17)
C4—N1—C1—C23.70 (19)N1—C1—C2—C34.46 (19)
C5—N1—C1—C2171.08 (14)O1—C1—C2—C3176.17 (17)
C4—N1—C5—N292.60 (18)C1—C2—C3—C43.57 (19)
C1—N1—C4—O2178.49 (15)C2—C3—C4—N11.57 (18)
C5—N1—C4—O211.2 (2)C2—C3—C4—O2178.63 (17)
C5—N1—C4—C3168.58 (13)N2—C6—C7—O357.18 (17)
C1—N1—C5—N2101.46 (17)O3—C8—C9—N257.76 (19)
C5—N2—C9—C8171.70 (14)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x, y+1, z; (iv) x1, y, z; (v) x+3/2, y1/2, z+1/2; (vi) x, y1, z; (vii) x+1, y+1, z; (viii) x+1/2, y1/2, z+1/2; (ix) x+1/2, y+1/2, z+1/2; (x) x+3/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···O2iv0.972.333.265 (2)162
C5—H5B···O10.972.562.886 (2)100
Symmetry code: (iv) x1, y, z.

Experimental details

Crystal data
Chemical formulaC9H14N2O3
Mr198.22
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)6.1368 (2), 7.8038 (3), 20.9032 (8)
β (°) 98.202 (2)
V3)990.82 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.26 × 0.18 × 0.18
Data collection
DiffractometerBruker Kappa-APEX2
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.974, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
8190, 1726, 1184
Rint0.026
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.089, 1.02
No. of reflections1726
No. of parameters127
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.12, 0.13

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···O2i0.972.333.265 (2)162
C5—H5B···O10.972.562.886 (2)100
Symmetry code: (i) x1, y, z.
 

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