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The title compound, C12H12N2O2, crystallizes in the triclinic space group P\overline 1 with two crystallographically independent mol­ecules in the asymmetric unit. These two mol­ecules differ slightly in the relative orientation of the phenyl and oxazoline rings. The molecular packing in the crystal is stabilized by C—H...O hydrogen bonds and van der Waals interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009832/ci6129sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009832/ci6129Isup2.hkl
Contains datablock I

CCDC reference: 189895

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.055
  • wR factor = 0.163
  • Data-to-parameter ratio = 13.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP97 (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.

4-(N,N-dimethylaminomethylene)-2-phenyl-2-oxazolin-5-one top
Crystal data top
C12H12N2O2Z = 4
Mr = 216.24F(000) = 456
Triclinic, P1Dx = 1.311 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.416 (6) ÅCell parameters from 25 reflections
b = 11.288 (3) Åθ = 10–15°
c = 12.097 (3) ŵ = 0.09 mm1
α = 85.39 (3)°T = 293 K
β = 73.97 (4)°Plate, orange
γ = 83.31 (4)°0.6 × 0.15 × 0.1 mm
V = 1095.6 (9) Å3
Data collection top
Enraf-Nonius CAD4
diffractometer
2681 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.014
Graphite monochromatorθmax = 25.0°, θmin = 2.5°
ω–2θ scansh = 99
Absorption correction: ψ scan
(North et al., 1968)
k = 1313
Tmin = 0.947, Tmax = 0.991l = 1314
4344 measured reflections2 standard reflections every 120 min
3849 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.163 w = 1/[σ2(Fo2) + (0.0814P)2 + 0.2456P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.001
3849 reflectionsΔρmax = 0.20 e Å3
293 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.008 (2)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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*/UeqOcc. (<1)
O1A0.1425 (2)0.24022 (14)0.41276 (13)0.0553 (4)
C2A0.0470 (3)0.2493 (2)0.29939 (18)0.0472 (5)
N3A0.0880 (2)0.34311 (17)0.24188 (16)0.0497 (5)
C4A0.2219 (3)0.4054 (2)0.31817 (19)0.0459 (5)
C5A0.2588 (3)0.3400 (2)0.42642 (19)0.0511 (6)
O5A0.3624 (2)0.35408 (18)0.51864 (15)0.0752 (6)
C6A0.3136 (3)0.5111 (2)0.30065 (19)0.0491 (6)
H6A0.39810.53610.36440.059*
N7A0.2994 (2)0.58249 (17)0.20684 (17)0.0559 (5)
C8A0.4145 (3)0.6895 (2)0.2066 (2)0.0660 (7)
H8A0.48980.69750.28190.099*
H8B0.47630.68300.15170.099*
H8C0.35340.75830.18590.099*
C9A0.1760 (4)0.5592 (3)0.0989 (2)0.0758 (8)
H9A0.11790.48150.10440.114*
H9B0.09850.61850.08240.114*
H9C0.22980.56210.03810.114*
C10A0.0841 (3)0.1549 (2)0.2610 (2)0.0487 (6)
C11A0.1708 (3)0.1522 (2)0.1449 (2)0.0596 (7)
H11A0.14600.21210.09310.072*
C12A0.2917 (3)0.0624 (3)0.1070 (3)0.0732 (8)
H12A0.34900.06130.02940.088*
C13A0.3301 (4)0.0275 (3)0.1831 (3)0.0762 (8)
H13A0.41240.08890.15650.091*
C14A0.2473 (4)0.0254 (3)0.2964 (3)0.0757 (8)
H14A0.27380.08520.34760.091*
C15A0.1237 (3)0.0649 (2)0.3362 (2)0.0610 (7)
H15A0.06700.06520.41390.073*
O1B0.7197 (2)0.17589 (15)0.08418 (13)0.0653 (5)
C2B0.6560 (3)0.1414 (2)0.19949 (18)0.0521 (6)
N3B0.5385 (3)0.21287 (17)0.25692 (16)0.0524 (5)
C4B0.5141 (3)0.3073 (2)0.17766 (19)0.0552 (6)
C5B0.6291 (4)0.2846 (2)0.0690 (2)0.0660 (7)
O5B0.6590 (3)0.33865 (19)0.02528 (16)0.0972 (8)
C6B0.4009 (3)0.4056 (2)0.1949 (2)0.0566 (6)
H6B0.40320.45530.12940.068*
N7B0.2892 (3)0.44204 (18)0.28840 (18)0.0596 (6)
C8B0.1771 (3)0.5498 (2)0.2870 (3)0.0674 (7)
H8D0.19750.58480.21000.101*
H8E0.19520.60570.33700.101*
H8F0.06430.53020.31310.101*
C9B0.2669 (4)0.3762 (2)0.3997 (2)0.0666 (7)
H9D0.17960.41760.45630.100*0.50
H9E0.36840.37000.42230.100*0.50
H9F0.23800.29760.39350.100*0.50
H9G0.34440.30590.39180.100*0.50
H9H0.15560.35350.42580.100*0.50
H9I0.28600.42580.45460.100*0.50
C10B0.7298 (3)0.0292 (2)0.2398 (2)0.0510 (6)
C11B0.6683 (3)0.0102 (2)0.3540 (2)0.0653 (7)
H11B0.58040.03440.40250.078*
C12B0.7370 (4)0.1147 (3)0.3952 (3)0.0774 (9)
H12B0.69410.14080.47140.093*
C13B0.8674 (4)0.1814 (3)0.3263 (3)0.0766 (8)
H13B0.91370.25150.35590.092*
C14B0.9298 (4)0.1441 (3)0.2131 (3)0.0723 (8)
H14B1.01820.18900.16550.087*
C15B0.8599 (3)0.0391 (2)0.1700 (2)0.0594 (6)
H15B0.90140.01450.09320.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0621 (10)0.0548 (10)0.0392 (9)0.0061 (8)0.0037 (7)0.0036 (7)
C2A0.0492 (12)0.0468 (13)0.0411 (12)0.0044 (10)0.0047 (10)0.0026 (10)
N3A0.0536 (11)0.0463 (11)0.0426 (10)0.0020 (9)0.0039 (9)0.0006 (8)
C4A0.0483 (12)0.0440 (12)0.0398 (12)0.0014 (10)0.0041 (10)0.0018 (9)
C5A0.0537 (13)0.0547 (14)0.0380 (13)0.0060 (11)0.0052 (11)0.0032 (10)
O5A0.0828 (13)0.0787 (13)0.0435 (10)0.0186 (10)0.0050 (9)0.0012 (9)
C6A0.0491 (13)0.0498 (13)0.0444 (13)0.0028 (11)0.0068 (10)0.0019 (10)
N7A0.0609 (12)0.0460 (11)0.0515 (12)0.0010 (9)0.0047 (10)0.0067 (9)
C8A0.0638 (16)0.0544 (15)0.0727 (18)0.0058 (13)0.0145 (14)0.0092 (13)
C9A0.090 (2)0.0718 (19)0.0476 (15)0.0006 (16)0.0042 (14)0.0127 (13)
C10A0.0469 (12)0.0450 (13)0.0506 (13)0.0026 (10)0.0085 (10)0.0005 (10)
C11A0.0576 (14)0.0552 (15)0.0542 (15)0.0044 (12)0.0010 (12)0.0037 (11)
C12A0.0631 (16)0.0742 (19)0.0665 (18)0.0083 (14)0.0046 (14)0.0092 (15)
C13A0.0603 (16)0.0644 (18)0.089 (2)0.0175 (14)0.0054 (15)0.0056 (16)
C14A0.0702 (18)0.0619 (18)0.088 (2)0.0107 (15)0.0211 (17)0.0123 (15)
C15A0.0608 (15)0.0592 (16)0.0560 (15)0.0011 (13)0.0098 (12)0.0067 (12)
O1B0.0967 (13)0.0573 (11)0.0359 (9)0.0085 (10)0.0109 (9)0.0102 (7)
C2B0.0703 (16)0.0502 (14)0.0350 (12)0.0132 (12)0.0133 (11)0.0099 (10)
N3B0.0680 (13)0.0457 (11)0.0428 (11)0.0087 (10)0.0168 (9)0.0116 (9)
C4B0.0808 (17)0.0451 (13)0.0422 (13)0.0114 (12)0.0229 (12)0.0121 (10)
C5B0.102 (2)0.0527 (15)0.0438 (14)0.0053 (15)0.0245 (14)0.0078 (11)
O5B0.164 (2)0.0775 (14)0.0395 (11)0.0022 (14)0.0198 (12)0.0215 (9)
C6B0.0775 (17)0.0487 (14)0.0481 (14)0.0121 (13)0.0260 (13)0.0117 (11)
N7B0.0720 (14)0.0513 (12)0.0555 (13)0.0066 (10)0.0219 (11)0.0160 (10)
C8B0.0694 (17)0.0549 (16)0.0760 (19)0.0019 (13)0.0244 (14)0.0140 (13)
C9B0.0799 (18)0.0586 (16)0.0532 (15)0.0046 (14)0.0106 (13)0.0168 (12)
C10B0.0562 (14)0.0484 (13)0.0463 (13)0.0078 (11)0.0111 (11)0.0050 (10)
C11B0.0708 (16)0.0618 (16)0.0489 (15)0.0065 (13)0.0018 (12)0.0128 (12)
C12B0.089 (2)0.0671 (18)0.0611 (17)0.0128 (16)0.0114 (15)0.0229 (14)
C13B0.080 (2)0.0602 (17)0.081 (2)0.0117 (15)0.0187 (17)0.0104 (15)
C14B0.0639 (17)0.0625 (17)0.084 (2)0.0047 (14)0.0122 (15)0.0089 (15)
C15B0.0644 (15)0.0573 (15)0.0509 (14)0.0102 (13)0.0050 (12)0.0008 (12)
Geometric parameters (Å, º) top
O1A—C2A1.387 (3)C2B—N3B1.279 (3)
O1A—C5A1.392 (3)C2B—C10B1.454 (3)
C2A—N3A1.285 (3)N3B—C4B1.411 (3)
C2A—C10A1.447 (3)C4B—C6B1.365 (4)
N3A—C4A1.401 (3)C4B—C5B1.422 (4)
C4A—C6A1.378 (3)C5B—O5B1.226 (3)
C4A—C5A1.425 (3)C6B—N7B1.315 (3)
C5A—O5A1.220 (3)C6B—H6B0.93
C6A—N7A1.323 (3)N7B—C8B1.452 (3)
C6A—H6A0.93N7B—C9B1.460 (3)
N7A—C9A1.448 (3)C8B—H8D0.96
N7A—C8A1.458 (3)C8B—H8E0.96
C8A—H8A0.96C8B—H8F0.96
C8A—H8B0.96C9B—H9D0.96
C8A—H8C0.96C9B—H9E0.96
C9A—H9A0.96C9B—H9F0.96
C9A—H9B0.96C9B—H9G0.96
C9A—H9C0.96C9B—H9H0.96
C10A—C15A1.382 (4)C9B—H9I0.96
C10A—C11A1.393 (3)C10B—C15B1.380 (4)
C11A—C12A1.360 (4)C10B—C11B1.391 (3)
C11A—H11A0.93C11B—C12B1.372 (4)
C12A—C13A1.385 (4)C11B—H11B0.93
C12A—H12A0.93C12B—C13B1.367 (4)
C13A—C14A1.356 (4)C12B—H12B0.93
C13A—H13A0.93C13B—C14B1.375 (4)
C14A—C15A1.381 (4)C13B—H13B0.93
C14A—H14A0.93C14B—C15B1.389 (4)
C15A—H15A0.93C14B—H14B0.93
O1B—C2B1.391 (3)C15B—H15B0.93
O1B—C5B1.395 (3)
C2A—O1A—C5A105.59 (17)O5B—C5B—O1B119.9 (3)
N3A—C2A—O1A114.3 (2)O5B—C5B—C4B134.0 (3)
N3A—C2A—C10A128.4 (2)O1B—C5B—C4B106.1 (2)
O1A—C2A—C10A117.3 (2)N7B—C6B—C4B130.9 (2)
C2A—N3A—C4A105.86 (19)N7B—C6B—H6B114.5
C6A—C4A—N3A129.9 (2)C4B—C6B—H6B114.5
C6A—C4A—C5A121.3 (2)C6B—N7B—C8B121.9 (2)
N3A—C4A—C5A108.78 (19)C6B—N7B—C9B122.6 (2)
O5A—C5A—O1A119.9 (2)C8B—N7B—C9B115.5 (2)
O5A—C5A—C4A134.7 (2)N7B—C8B—H8D109.5
O1A—C5A—C4A105.42 (18)N7B—C8B—H8E109.5
N7A—C6A—C4A129.8 (2)H8D—C8B—H8E109.5
N7A—C6A—H6A115.1N7B—C8B—H8F109.5
C4A—C6A—H6A115.1H8D—C8B—H8F109.5
C6A—N7A—C9A123.5 (2)H8E—C8B—H8F109.5
C6A—N7A—C8A120.5 (2)N7B—C9B—H9D109.5
C9A—N7A—C8A115.9 (2)N7B—C9B—H9E109.5
N7A—C8A—H8A109.5H9D—C9B—H9E109.5
N7A—C8A—H8B109.5N7B—C9B—H9F109.5
H8A—C8A—H8B109.5H9D—C9B—H9F109.5
N7A—C8A—H8C109.5H9E—C9B—H9F109.5
H8A—C8A—H8C109.5N7B—C9B—H9G109.5
H8B—C8A—H8C109.5H9D—C9B—H9G141.1
N7A—C9A—H9A109.5H9E—C9B—H9G56.3
N7A—C9A—H9B109.5H9F—C9B—H9G56.3
H9A—C9A—H9B109.5N7B—C9B—H9H109.5
N7A—C9A—H9C109.5H9D—C9B—H9H56.3
H9A—C9A—H9C109.5H9E—C9B—H9H141.1
H9B—C9A—H9C109.5H9F—C9B—H9H56.3
C15A—C10A—C11A118.7 (2)H9G—C9B—H9H109.5
C15A—C10A—C2A121.7 (2)N7B—C9B—H9I109.5
C11A—C10A—C2A119.6 (2)H9D—C9B—H9I56.3
C12A—C11A—C10A120.3 (3)H9E—C9B—H9I56.3
C12A—C11A—H11A119.9H9F—C9B—H9I141.1
C10A—C11A—H11A119.9H9G—C9B—H9I109.5
C11A—C12A—C13A120.6 (3)H9H—C9B—H9I109.5
C11A—C12A—H12A119.7C15B—C10B—C11B118.6 (2)
C13A—C12A—H12A119.7C15B—C10B—C2B122.8 (2)
C14A—C13A—C12A119.7 (3)C11B—C10B—C2B118.6 (2)
C14A—C13A—H13A120.2C12B—C11B—C10B120.0 (3)
C12A—C13A—H13A120.2C12B—C11B—H11B120.0
C13A—C14A—C15A120.5 (3)C10B—C11B—H11B120.0
C13A—C14A—H14A119.8C13B—C12B—C11B121.3 (3)
C15A—C14A—H14A119.8C13B—C12B—H12B119.4
C14A—C15A—C10A120.3 (3)C11B—C12B—H12B119.4
C14A—C15A—H15A119.9C12B—C13B—C14B119.5 (3)
C10A—C15A—H15A119.9C12B—C13B—H13B120.2
C2B—O1B—C5B104.6 (2)C14B—C13B—H13B120.2
N3B—C2B—O1B115.5 (2)C13B—C14B—C15B119.7 (3)
N3B—C2B—C10B128.1 (2)C13B—C14B—H14B120.1
O1B—C2B—C10B116.5 (2)C15B—C14B—H14B120.1
C2B—N3B—C4B105.2 (2)C10B—C15B—C14B120.8 (3)
C6B—C4B—N3B128.8 (2)C10B—C15B—H15B119.6
C6B—C4B—C5B122.6 (2)C14B—C15B—H15B119.6
N3B—C4B—C5B108.6 (2)
C5A—O1A—C2A—N3A1.1 (3)C5B—O1B—C2B—N3B0.5 (3)
C5A—O1A—C2A—C10A179.19 (19)C5B—O1B—C2B—C10B179.7 (2)
O1A—C2A—N3A—C4A0.3 (3)O1B—C2B—N3B—C4B0.0 (3)
C10A—C2A—N3A—C4A180.0 (2)C10B—C2B—N3B—C4B179.8 (2)
C2A—N3A—C4A—C6A179.5 (2)C2B—N3B—C4B—C6B178.6 (2)
C2A—N3A—C4A—C5A0.6 (2)C2B—N3B—C4B—C5B0.5 (3)
C2A—O1A—C5A—O5A178.7 (2)C2B—O1B—C5B—O5B179.1 (3)
C2A—O1A—C5A—C4A1.3 (2)C2B—O1B—C5B—C4B0.8 (3)
C6A—C4A—C5A—O5A0.2 (4)C6B—C4B—C5B—O5B1.7 (5)
N3A—C4A—C5A—O5A178.8 (3)N3B—C4B—C5B—O5B179.1 (3)
C6A—C4A—C5A—O1A179.8 (2)C6B—C4B—C5B—O1B178.4 (2)
N3A—C4A—C5A—O1A1.2 (2)N3B—C4B—C5B—O1B0.8 (3)
N3A—C4A—C6A—N7A0.1 (4)N3B—C4B—C6B—N7B2.7 (5)
C5A—C4A—C6A—N7A178.9 (2)C5B—C4B—C6B—N7B178.3 (2)
C4A—C6A—N7A—C9A0.1 (4)C4B—C6B—N7B—C8B178.6 (3)
C4A—C6A—N7A—C8A178.1 (2)C4B—C6B—N7B—C9B0.1 (4)
N3A—C2A—C10A—C15A173.7 (2)N3B—C2B—C10B—C15B178.2 (2)
O1A—C2A—C10A—C15A6.0 (3)O1B—C2B—C10B—C15B2.0 (3)
N3A—C2A—C10A—C11A7.8 (4)N3B—C2B—C10B—C11B0.9 (4)
O1A—C2A—C10A—C11A172.5 (2)O1B—C2B—C10B—C11B178.9 (2)
C15A—C10A—C11A—C12A0.1 (4)C15B—C10B—C11B—C12B0.2 (4)
C2A—C10A—C11A—C12A178.4 (2)C2B—C10B—C11B—C12B179.0 (3)
C10A—C11A—C12A—C13A0.0 (4)C10B—C11B—C12B—C13B0.8 (5)
C11A—C12A—C13A—C14A0.4 (5)C11B—C12B—C13B—C14B1.0 (5)
C12A—C13A—C14A—C15A0.7 (5)C12B—C13B—C14B—C15B0.2 (5)
C13A—C14A—C15A—C10A0.5 (4)C11B—C10B—C15B—C14B0.9 (4)
C11A—C10A—C15A—C14A0.1 (4)C2B—C10B—C15B—C14B178.2 (2)
C2A—C10A—C15A—C14A178.7 (2)C13B—C14B—C15B—C10B0.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6A—H6A···O5Ai0.932.393.287 (4)161
C8A—H8A···O5Ai0.962.453.365 (4)160
C8B—H8D···O5Bii0.962.383.296 (5)161
Symmetry codes: (i) x1, y+1, z+1; (ii) x+1, y+1, z.
 

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