Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046053/bt2514sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046053/bt2514Isup2.hkl |
CCDC reference: 660711
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
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.
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).
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).
C9H14N2O3 | F(000) = 424 |
Mr = 198.22 | Dx = 1.329 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2548 reflections |
a = 6.1368 (2) Å | θ = 2.0–23.7° |
b = 7.8038 (3) Å | µ = 0.10 mm−1 |
c = 20.9032 (8) Å | T = 293 K |
β = 98.202 (2)° | Prism, colourless |
V = 990.82 (6) Å3 | 0.26 × 0.18 × 0.18 mm |
Z = 4 |
Bruker Kappa-APEX2 diffractometer | 1726 independent reflections |
Radiation source: fine focus sealed tube | 1184 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω and φ scans | θmax = 25°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −6→6 |
Tmin = 0.974, Tmax = 0.982 | k = −6→8 |
8190 measured reflections | l = −23→23 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H-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 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
C9H14N2O3 | V = 990.82 (6) Å3 |
Mr = 198.22 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.1368 (2) Å | µ = 0.10 mm−1 |
b = 7.8038 (3) Å | T = 293 K |
c = 20.9032 (8) Å | 0.26 × 0.18 × 0.18 mm |
β = 98.202 (2)° |
Bruker Kappa-APEX2 diffractometer | 1726 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1184 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.982 | Rint = 0.026 |
8190 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.12 e Å−3 |
1726 reflections | Δρmin = −0.13 e Å−3 |
127 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.0573 (2) | 0.26782 (18) | 0.07851 (6) | 0.0734 (5) | |
O2 | 0.6854 (2) | 0.35020 (16) | 0.21769 (5) | 0.0655 (5) | |
O3 | 0.4045 (2) | 0.94347 (16) | 0.10318 (6) | 0.0763 (5) | |
N1 | 0.3883 (2) | 0.33660 (15) | 0.13812 (5) | 0.0409 (4) | |
N2 | 0.4843 (2) | 0.59584 (16) | 0.07942 (5) | 0.0417 (4) | |
C1 | 0.1818 (3) | 0.2607 (2) | 0.12828 (8) | 0.0517 (6) | |
C2 | 0.1444 (3) | 0.1732 (3) | 0.18956 (9) | 0.0658 (7) | |
C3 | 0.3581 (3) | 0.1936 (2) | 0.23465 (8) | 0.0621 (7) | |
C4 | 0.5006 (3) | 0.3011 (2) | 0.19838 (7) | 0.0467 (6) | |
C5 | 0.4923 (3) | 0.4132 (2) | 0.08505 (7) | 0.0465 (6) | |
C6 | 0.2643 (3) | 0.6669 (2) | 0.06615 (7) | 0.0487 (6) | |
C7 | 0.2771 (3) | 0.8541 (2) | 0.05144 (9) | 0.0636 (7) | |
C8 | 0.6188 (3) | 0.8747 (3) | 0.11511 (10) | 0.0714 (8) | |
C9 | 0.6152 (3) | 0.6885 (2) | 0.13172 (7) | 0.0514 (6) | |
H2A | 0.11023 | 0.05294 | 0.18181 | 0.0790* | |
H2B | 0.02398 | 0.22664 | 0.20757 | 0.0790* | |
H3A | 0.33333 | 0.25000 | 0.27434 | 0.0746* | |
H3B | 0.42567 | 0.08294 | 0.24526 | 0.0746* | |
H5A | 0.64555 | 0.37833 | 0.09061 | 0.0558* | |
H5B | 0.42212 | 0.36475 | 0.04455 | 0.0558* | |
H6A | 0.18837 | 0.65066 | 0.10335 | 0.0585* | |
H6B | 0.18165 | 0.60800 | 0.02962 | 0.0585* | |
H7A | 0.34281 | 0.86915 | 0.01228 | 0.0762* | |
H7B | 0.12965 | 0.90176 | 0.04402 | 0.0762* | |
H8A | 0.70361 | 0.93659 | 0.15048 | 0.0857* | |
H8B | 0.69063 | 0.88966 | 0.07704 | 0.0857* | |
H9A | 0.76414 | 0.64376 | 0.13844 | 0.0616* | |
H9B | 0.55246 | 0.67330 | 0.17139 | 0.0616* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0646 (9) | 0.0780 (10) | 0.0687 (8) | −0.0037 (7) | −0.0209 (7) | 0.0066 (7) |
O2 | 0.0579 (9) | 0.0811 (10) | 0.0524 (7) | 0.0013 (7) | −0.0095 (6) | 0.0102 (6) |
O3 | 0.0862 (10) | 0.0493 (8) | 0.0854 (9) | 0.0096 (7) | −0.0156 (7) | −0.0157 (6) |
N1 | 0.0463 (8) | 0.0413 (8) | 0.0339 (6) | 0.0048 (6) | 0.0012 (5) | 0.0019 (5) |
N2 | 0.0479 (8) | 0.0437 (8) | 0.0327 (6) | 0.0038 (6) | 0.0032 (5) | 0.0010 (5) |
C1 | 0.0504 (10) | 0.0460 (11) | 0.0562 (10) | 0.0050 (8) | −0.0013 (8) | −0.0005 (8) |
C2 | 0.0614 (12) | 0.0686 (13) | 0.0694 (11) | −0.0025 (9) | 0.0158 (9) | 0.0113 (9) |
C3 | 0.0763 (13) | 0.0628 (12) | 0.0479 (10) | 0.0004 (9) | 0.0110 (9) | 0.0119 (8) |
C4 | 0.0515 (11) | 0.0473 (10) | 0.0395 (8) | 0.0094 (8) | 0.0000 (7) | 0.0010 (7) |
C5 | 0.0575 (10) | 0.0492 (11) | 0.0335 (8) | 0.0083 (8) | 0.0089 (7) | −0.0018 (7) |
C6 | 0.0508 (10) | 0.0512 (11) | 0.0407 (8) | 0.0037 (8) | −0.0053 (7) | 0.0007 (7) |
C7 | 0.0703 (13) | 0.0510 (12) | 0.0633 (11) | 0.0097 (9) | −0.0113 (9) | −0.0007 (8) |
C8 | 0.0716 (14) | 0.0591 (13) | 0.0773 (13) | −0.0117 (10) | −0.0110 (10) | 0.0001 (10) |
C9 | 0.0464 (10) | 0.0577 (11) | 0.0474 (9) | −0.0021 (8) | −0.0022 (7) | 0.0008 (8) |
O1—C1 | 1.201 (2) | C2—H2A | 0.9700 |
O2—C4 | 1.211 (2) | C2—H2B | 0.9700 |
O3—C7 | 1.423 (2) | C3—H3A | 0.9700 |
O3—C8 | 1.409 (2) | C3—H3B | 0.9700 |
N1—C1 | 1.387 (2) | C5—H5A | 0.9700 |
N1—C4 | 1.3750 (19) | C5—H5B | 0.9700 |
N1—C5 | 1.4823 (19) | C6—H6A | 0.9700 |
N2—C5 | 1.430 (2) | C6—H6B | 0.9700 |
N2—C6 | 1.449 (2) | C7—H7A | 0.9700 |
N2—C9 | 1.4535 (19) | C7—H7B | 0.9700 |
C1—C2 | 1.498 (3) | C8—H8A | 0.9700 |
C2—C3 | 1.510 (3) | C8—H8B | 0.9700 |
C3—C4 | 1.494 (2) | C9—H9A | 0.9700 |
C6—C7 | 1.497 (2) | C9—H9B | 0.9700 |
C8—C9 | 1.495 (3) | ||
O1···C6 | 3.387 (2) | C6···O1i | 3.405 (2) |
O1···C7i | 3.302 (2) | C6···O1 | 3.387 (2) |
O1···C6i | 3.405 (2) | C7···O1i | 3.302 (2) |
O2···C9 | 3.1881 (19) | C9···O2 | 3.1881 (19) |
O2···C2ii | 3.265 (2) | C9···C4 | 3.443 (2) |
O3···C3iii | 3.416 (2) | C1···H6A | 3.0900 |
O3···C1iii | 2.911 (2) | C4···H9B | 2.9800 |
O3···C2iii | 3.138 (2) | H2A···O3vi | 2.7500 |
O3···N2 | 2.8134 (18) | H2A···H3Aviii | 2.5400 |
O3···N1iii | 3.1585 (17) | H2B···O2iv | 2.3300 |
O1···H5Aiv | 2.7200 | H3A···H2Aix | 2.5400 |
O1···H6Bi | 2.6900 | H5A···O1ii | 2.7200 |
O1···H5B | 2.5600 | H5A···O2 | 2.6400 |
O2···H8Av | 2.8200 | H5A···H9A | 2.3700 |
O2···H9B | 2.7800 | H5B···O1 | 2.5600 |
O2···H2Bii | 2.3300 | H5B···H6B | 2.4000 |
O2···H5A | 2.6400 | H5B···N2vii | 2.7500 |
O2···H9A | 2.9100 | H6A···N1 | 2.7900 |
O3···H2Aiii | 2.7500 | H6A···C1 | 3.0900 |
N1···O3vi | 3.1585 (17) | H6A···H9B | 2.4800 |
N2···O3 | 2.8134 (18) | H6B···H5B | 2.4000 |
N1···H6A | 2.7900 | H6B···O1i | 2.6900 |
N1···H9B | 2.8600 | H7A···H8B | 2.3600 |
N2···H5Bvii | 2.7500 | H8A···O2x | 2.8200 |
C1···O3vi | 2.911 (2) | H8B···H7A | 2.3600 |
C1···C6 | 3.490 (2) | H9A···O2 | 2.9100 |
C2···O2iv | 3.265 (2) | H9A···H5A | 2.3700 |
C2···O3vi | 3.138 (2) | H9B···O2 | 2.7800 |
C3···O3vi | 3.416 (2) | H9B···N1 | 2.8600 |
C4···C9 | 3.443 (2) | H9B···C4 | 2.9800 |
C6···C1 | 3.490 (2) | H9B···H6A | 2.4800 |
C7—O3—C8 | 110.21 (14) | C4—C3—H3B | 111.00 |
C1—N1—C4 | 112.19 (13) | H3A—C3—H3B | 109.00 |
C1—N1—C5 | 122.88 (12) | N1—C5—H5A | 108.00 |
C4—N1—C5 | 123.63 (13) | N1—C5—H5B | 108.00 |
C5—N2—C6 | 114.65 (13) | N2—C5—H5A | 108.00 |
C5—N2—C9 | 115.15 (12) | N2—C5—H5B | 108.00 |
C6—N2—C9 | 110.70 (12) | H5A—C5—H5B | 107.00 |
O1—C1—N1 | 124.29 (15) | N2—C6—H6A | 110.00 |
O1—C1—C2 | 127.28 (17) | N2—C6—H6B | 110.00 |
N1—C1—C2 | 108.42 (14) | C7—C6—H6A | 110.00 |
C1—C2—C3 | 105.09 (15) | C7—C6—H6B | 110.00 |
C2—C3—C4 | 105.16 (14) | H6A—C6—H6B | 108.00 |
O2—C4—N1 | 124.40 (15) | O3—C7—H7A | 109.00 |
O2—C4—C3 | 126.64 (14) | O3—C7—H7B | 109.00 |
N1—C4—C3 | 108.96 (14) | C6—C7—H7A | 109.00 |
N1—C5—N2 | 116.74 (13) | C6—C7—H7B | 109.00 |
N2—C6—C7 | 109.75 (14) | H7A—C7—H7B | 108.00 |
O3—C7—C6 | 111.18 (14) | O3—C8—H8A | 109.00 |
O3—C8—C9 | 111.53 (16) | O3—C8—H8B | 109.00 |
N2—C9—C8 | 109.50 (13) | C9—C8—H8A | 109.00 |
C1—C2—H2A | 111.00 | C9—C8—H8B | 109.00 |
C1—C2—H2B | 111.00 | H8A—C8—H8B | 108.00 |
C3—C2—H2A | 111.00 | N2—C9—H9A | 110.00 |
C3—C2—H2B | 111.00 | N2—C9—H9B | 110.00 |
H2A—C2—H2B | 109.00 | C8—C9—H9A | 110.00 |
C2—C3—H3A | 111.00 | C8—C9—H9B | 110.00 |
C2—C3—H3B | 111.00 | H9A—C9—H9B | 108.00 |
C4—C3—H3A | 111.00 | ||
C7—O3—C8—C9 | −58.88 (19) | C9—N2—C6—C7 | 56.19 (16) |
C8—O3—C7—C6 | 58.47 (19) | C5—N2—C6—C7 | −171.49 (12) |
C5—N1—C1—O1 | −9.5 (2) | C6—N2—C5—N1 | −62.17 (16) |
C4—N1—C1—O1 | −176.91 (16) | C9—N2—C5—N1 | 68.00 (18) |
C1—N1—C4—C3 | −1.31 (18) | C6—N2—C9—C8 | −56.24 (17) |
C4—N1—C1—C2 | 3.70 (19) | N1—C1—C2—C3 | −4.46 (19) |
C5—N1—C1—C2 | 171.08 (14) | O1—C1—C2—C3 | 176.17 (17) |
C4—N1—C5—N2 | −92.60 (18) | C1—C2—C3—C4 | 3.57 (19) |
C1—N1—C4—O2 | 178.49 (15) | C2—C3—C4—N1 | −1.57 (18) |
C5—N1—C4—O2 | 11.2 (2) | C2—C3—C4—O2 | 178.63 (17) |
C5—N1—C4—C3 | −168.58 (13) | N2—C6—C7—O3 | −57.18 (17) |
C1—N1—C5—N2 | 101.46 (17) | O3—C8—C9—N2 | 57.76 (19) |
C5—N2—C9—C8 | 171.70 (14) |
Symmetry codes: (i) −x, −y+1, −z; (ii) x+1, y, z; (iii) x, y+1, z; (iv) x−1, y, z; (v) −x+3/2, y−1/2, −z+1/2; (vi) x, y−1, z; (vii) −x+1, −y+1, −z; (viii) −x+1/2, y−1/2, −z+1/2; (ix) −x+1/2, y+1/2, −z+1/2; (x) −x+3/2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···O2iv | 0.97 | 2.33 | 3.265 (2) | 162 |
C5—H5B···O1 | 0.97 | 2.56 | 2.886 (2) | 100 |
Symmetry code: (iv) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C9H14N2O3 |
Mr | 198.22 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 6.1368 (2), 7.8038 (3), 20.9032 (8) |
β (°) | 98.202 (2) |
V (Å3) | 990.82 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.26 × 0.18 × 0.18 |
Data collection | |
Diffractometer | Bruker Kappa-APEX2 |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.974, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8190, 1726, 1184 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.089, 1.02 |
No. of reflections | 1726 |
No. of parameters | 127 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.13 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···O2i | 0.97 | 2.33 | 3.265 (2) | 162 |
C5—H5B···O1 | 0.97 | 2.56 | 2.886 (2) | 100 |
Symmetry code: (i) x−1, y, z. |
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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.