


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989014026292/hb7328sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989014026292/hb7328Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989014026292/hb7328Isup3.cml |
CCDC reference: 1036843
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.111
- Data-to-parameter ratio = 19.2
checkCIF/PLATON results
No syntax errors found
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
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.
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,
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);
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).
![]() | Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms. |
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 |
C18H20N2O2 | V = 3140.1 (3) Å3 |
Mr = 296.36 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 12.4554 (6) Å | µ = 0.08 mm−1 |
b = 8.2204 (4) Å | T = 295 K |
c = 30.6681 (17) Å | 0.20 × 0.15 × 0.10 mm |
Bruker APEXII CCD diffractometer | 3812 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2547 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 0.975 | Rint = 0.028 |
16093 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.14 e Å−3 |
3812 reflections | Δρmin = −0.16 e Å−3 |
199 parameters |
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) |
Cg2 is the centroid of the C10–C14/N1 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg2i | 0.93 | 2.90 | 3.780 (6) | 159 |
Symmetry code: (i) −x, −y+1, −z. |
Cg2 is the centroid of the C10–C14/N1 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg2i | 0.93 | 2.90 | 3.780 (6) | 159 |
Symmetry code: (i) −x, −y+1, −z. |
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.