



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810018635/ez2209sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810018635/ez2209Isup2.hkl |
CCDC reference: 781416
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.065
- wR factor = 0.220
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 2
Alert level G PLAT931_ALERT_5_G Check Twin Law ( 0 0 1)[ ] Estimated BASF 0.27 PLAT931_ALERT_5_G Check Twin Law ( )[ 2 0 5] Estimated BASF 0.27
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 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 1 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: The contribution of the authors to this submission is as follows: |
Gilberto A. Romeiro co-supervisor Carlos M. R. Ribeiro student Solange M. S. V.Wardell co-supervisor James L. Wardell spectroscopist and co-responsible for write-up Ng Seik Weng final crystallography Edward R. T. Tiekink crystallography and co-responsible for write-up
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
The title compound was prepared as per published procedures (Singh & Singh, 1994; Singh et al., 1994). Physical properties were in agreement with published data. The crystal used in the structure determination was grown from EtOH solution.
The C-bound H atoms were geometrically placed (C–H = 0.95–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). For the treatment of twinned diffraction data, see: Spek (2009).
The preparations of 4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-one derivatives have been reported using the Vilsmeier-Haack reactions (Meth-Cohn & Stanforth, 1991) of acylaminoacetanilides with POCl3 and DMF (Singh & Singh, 1994; Takahashi & Izawa, 2005; Singh et al., 1994; Kmetic & Stanovnik, 1995). The compounds have been used as precursors of 4-hydroxymethylene-2-aryl-2-oxazolin-5-one, which have been tested for anti-bacterial activities (Singh & Singh, 2008). The crystal structures of 4-(N,N-dimethylaminomethylene)-2-phenyl-2-oxazolin-5-one (Vasuki et al., 2002) and 4-(N,N-dimethylaminomethylene)-2-(2-nitrophenyl)-2-oxazolin-5-one (Vijayalakshmi et al., 1998) have been reported. We now report the crystal structure of 4-(N,N-dimethylaminomethylene)-2-(4-nitrophenyl)-2-oxazolin-5-one, (I).
The molecule of (I), Fig. 1, is essentially planar with the maximum deviations from the least-squares plane through all non-hydrogen atoms being 0.157 (4) Å for atom C5 and -0.158 (3) for atom O4; the r.m.s. = 0.068 Å. The sequence of C1–N1, N1–C2, C2–C4, and C4–N2 bond distances of 1.289 (4), 1.398 (4), 1.382 (5), and 1.317 (4) Å, respectively, indicate substantial delocalisation of π-electron density over these atoms. The geometric parameters in (I) match closely those found in the parent compound, namely 4-(N,N-dimethylaminomethylene)-2-phenyl-2-oxazolin-5-one (Vasuki et al., 2002) and in the 2-nitro derivative (Vijayalakshmi et al., 1998).
The crystal packing is dominated by C–H···O and π–π interactions; the N1 atom of the oxazolin-5-one is involved in an intramolecular C–H···N contact that shields this atom from forming intermolecular interactions, Table 1. Columns of molecules orientated along the b axis are stabilised by π–π contacts with the shortest of these occurring between centrosymmetrically related benzene rings [ring centroid(C7–C12)···ring centroid(C7–C12)i = 3.6312 (16) Å for i: 1-x, 1-y, 2-z]. The benzene rings also form π–π interactions with the oxazolin-5-one rings [ring centroid(C7–C12)···ring centroid(O1,N1,C1–C3)ii = 3.7645 (17) Å for ii: 1-x, -y, 2-z] to form a supramolecular chain, Fig. 2. The chains are connected by a series of C–H···O contacts, Table 1, to form a 3-D network, Fig. 3.
For the synthesis, synthetic uses and properties of 4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-one derivatives, see: Singh & Singh (1994, 2008); Takahashi & Izawa (2005); Singh et al. (1994); Kmetic & Stanovnik (1995). For the Vilsmeier–Haack reaction, see: Meth-Cohn & Stanforth (1991). For related structures, see Vasuki et al. (2002); Vijayalakshmi et al. (1998). For the treatment of twinned diffraction data, see: Spek (2009).
Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
C12H11N3O4 | F(000) = 544 |
Mr = 261.24 | Dx = 1.531 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2714 reflections |
a = 9.5313 (2) Å | θ = 2.9–27.5° |
b = 9.5204 (3) Å | µ = 0.12 mm−1 |
c = 13.0349 (4) Å | T = 120 K |
β = 106.661 (2)° | Block, red |
V = 1133.15 (6) Å3 | 0.42 × 0.38 × 0.22 mm |
Z = 4 |
Nonius KappaCCD area-detector diffractometer | 2581 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 2030 reflections with I > 2σ(I) |
10 cm confocal mirrors monochromator | Rint = 0.071 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.4°, θmin = 3.1° |
φ and ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | k = −12→11 |
Tmin = 0.661, Tmax = 1.000 | l = −16→16 |
14210 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.065 | H-atom parameters constrained |
wR(F2) = 0.220 | w = 1/[σ2(Fo2) + (0.0936P)2 + 1.6594P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max = 0.001 |
2581 reflections | Δρmax = 0.33 e Å−3 |
176 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.018 (5) |
C12H11N3O4 | V = 1133.15 (6) Å3 |
Mr = 261.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.5313 (2) Å | µ = 0.12 mm−1 |
b = 9.5204 (3) Å | T = 120 K |
c = 13.0349 (4) Å | 0.42 × 0.38 × 0.22 mm |
β = 106.661 (2)° |
Nonius KappaCCD area-detector diffractometer | 2581 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | 2030 reflections with I > 2σ(I) |
Tmin = 0.661, Tmax = 1.000 | Rint = 0.071 |
14210 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.220 | H-atom parameters constrained |
S = 1.19 | Δρmax = 0.33 e Å−3 |
2581 reflections | Δρmin = −0.30 e Å−3 |
176 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2σ(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 | 0.3806 (2) | 0.5986 (2) | 0.33548 (17) | 0.0197 (5) | |
O2 | 0.2556 (3) | 0.4481 (2) | 0.20576 (17) | 0.0239 (6) | |
O3 | 0.8419 (3) | 1.1001 (3) | 0.6327 (2) | 0.0324 (6) | |
O4 | 0.7443 (3) | 1.0746 (3) | 0.76142 (19) | 0.0307 (6) | |
N1 | 0.2875 (3) | 0.5457 (3) | 0.4711 (2) | 0.0180 (6) | |
N2 | 0.0528 (3) | 0.3059 (3) | 0.4441 (2) | 0.0203 (6) | |
N3 | 0.7556 (3) | 1.0430 (3) | 0.6733 (2) | 0.0209 (6) | |
C1 | 0.3786 (3) | 0.6220 (3) | 0.4393 (2) | 0.0166 (6) | |
C2 | 0.2186 (3) | 0.4617 (3) | 0.3831 (2) | 0.0179 (6) | |
C3 | 0.2761 (3) | 0.4921 (3) | 0.2958 (2) | 0.0195 (7) | |
C4 | 0.1130 (3) | 0.3590 (3) | 0.3735 (2) | 0.0189 (7) | |
H4 | 0.0778 | 0.3199 | 0.3038 | 0.023* | |
C5 | 0.0939 (4) | 0.3462 (4) | 0.5569 (3) | 0.0237 (7) | |
H5A | 0.1378 | 0.2655 | 0.6012 | 0.036* | |
H5B | 0.0066 | 0.3768 | 0.5761 | 0.036* | |
H5C | 0.1649 | 0.4233 | 0.5691 | 0.036* | |
C6 | −0.0548 (4) | 0.1947 (4) | 0.4138 (3) | 0.0284 (8) | |
H6A | −0.0780 | 0.1778 | 0.3366 | 0.043* | |
H6B | −0.1440 | 0.2223 | 0.4317 | 0.043* | |
H6C | −0.0152 | 0.1086 | 0.4526 | 0.043* | |
C7 | 0.4765 (3) | 0.7290 (3) | 0.4994 (2) | 0.0168 (6) | |
C8 | 0.4797 (3) | 0.7571 (3) | 0.6051 (2) | 0.0184 (6) | |
H8 | 0.4184 | 0.7056 | 0.6375 | 0.022* | |
C9 | 0.5715 (3) | 0.8590 (3) | 0.6624 (2) | 0.0185 (6) | |
H9 | 0.5735 | 0.8794 | 0.7342 | 0.022* | |
C10 | 0.6608 (3) | 0.9314 (3) | 0.6135 (2) | 0.0178 (6) | |
C11 | 0.6608 (3) | 0.9058 (3) | 0.5089 (2) | 0.0173 (6) | |
H11 | 0.7231 | 0.9571 | 0.4772 | 0.021* | |
C12 | 0.5676 (3) | 0.8035 (3) | 0.4519 (2) | 0.0175 (6) | |
H12 | 0.5655 | 0.7838 | 0.3800 | 0.021* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0239 (12) | 0.0203 (11) | 0.0177 (11) | −0.0022 (9) | 0.0105 (9) | −0.0010 (8) |
O2 | 0.0307 (13) | 0.0242 (12) | 0.0187 (11) | −0.0017 (10) | 0.0100 (10) | −0.0029 (9) |
O3 | 0.0323 (14) | 0.0382 (15) | 0.0291 (13) | −0.0147 (12) | 0.0127 (11) | −0.0044 (11) |
O4 | 0.0397 (15) | 0.0328 (14) | 0.0219 (12) | −0.0061 (12) | 0.0125 (11) | −0.0075 (10) |
N1 | 0.0195 (13) | 0.0171 (12) | 0.0183 (13) | 0.0003 (10) | 0.0067 (10) | 0.0004 (10) |
N2 | 0.0209 (13) | 0.0163 (13) | 0.0248 (13) | 0.0015 (11) | 0.0082 (11) | 0.0025 (10) |
N3 | 0.0219 (13) | 0.0210 (13) | 0.0195 (13) | 0.0017 (12) | 0.0056 (11) | 0.0024 (11) |
C1 | 0.0193 (14) | 0.0179 (14) | 0.0143 (13) | 0.0046 (12) | 0.0073 (11) | 0.0029 (11) |
C2 | 0.0198 (15) | 0.0172 (14) | 0.0173 (14) | 0.0032 (12) | 0.0065 (12) | 0.0009 (11) |
C3 | 0.0218 (15) | 0.0165 (14) | 0.0207 (15) | 0.0022 (12) | 0.0068 (12) | 0.0030 (12) |
C4 | 0.0222 (16) | 0.0156 (14) | 0.0198 (15) | 0.0042 (12) | 0.0076 (12) | 0.0024 (11) |
C5 | 0.0270 (17) | 0.0235 (16) | 0.0246 (16) | 0.0024 (14) | 0.0136 (14) | 0.0033 (13) |
C6 | 0.0247 (17) | 0.0210 (16) | 0.039 (2) | −0.0050 (14) | 0.0077 (15) | 0.0059 (14) |
C7 | 0.0182 (15) | 0.0145 (14) | 0.0185 (14) | 0.0035 (12) | 0.0062 (12) | 0.0022 (11) |
C8 | 0.0201 (15) | 0.0188 (15) | 0.0184 (14) | 0.0018 (12) | 0.0089 (12) | 0.0040 (12) |
C9 | 0.0215 (15) | 0.0193 (15) | 0.0158 (13) | 0.0052 (13) | 0.0070 (12) | 0.0030 (12) |
C10 | 0.0174 (14) | 0.0152 (14) | 0.0198 (15) | 0.0025 (12) | 0.0036 (12) | −0.0005 (11) |
C11 | 0.0180 (14) | 0.0175 (14) | 0.0178 (14) | 0.0023 (12) | 0.0073 (11) | 0.0035 (11) |
C12 | 0.0193 (14) | 0.0184 (14) | 0.0169 (14) | 0.0029 (12) | 0.0086 (12) | 0.0014 (11) |
O1—C1 | 1.377 (3) | C5—H5B | 0.9800 |
O1—C3 | 1.411 (4) | C5—H5C | 0.9800 |
O2—C3 | 1.209 (4) | C6—H6A | 0.9800 |
O3—N3 | 1.226 (4) | C6—H6B | 0.9800 |
O4—N3 | 1.222 (4) | C6—H6C | 0.9800 |
N1—C1 | 1.289 (4) | C7—C8 | 1.394 (4) |
N1—C2 | 1.398 (4) | C7—C12 | 1.396 (4) |
N2—C4 | 1.317 (4) | C8—C9 | 1.375 (4) |
N2—C6 | 1.448 (4) | C8—H8 | 0.9500 |
N2—C5 | 1.460 (4) | C9—C10 | 1.385 (4) |
N3—C10 | 1.466 (4) | C9—H9 | 0.9500 |
C1—C7 | 1.450 (4) | C10—C11 | 1.385 (4) |
C2—C4 | 1.382 (5) | C11—C12 | 1.383 (4) |
C2—C3 | 1.428 (4) | C11—H11 | 0.9500 |
C4—H4 | 0.9500 | C12—H12 | 0.9500 |
C5—H5A | 0.9800 | ||
C1—O1—C3 | 105.6 (2) | H5B—C5—H5C | 109.5 |
C1—N1—C2 | 105.0 (2) | N2—C6—H6A | 109.5 |
C4—N2—C6 | 120.5 (3) | N2—C6—H6B | 109.5 |
C4—N2—C5 | 123.9 (3) | H6A—C6—H6B | 109.5 |
C6—N2—C5 | 115.5 (3) | N2—C6—H6C | 109.5 |
O4—N3—O3 | 123.2 (3) | H6A—C6—H6C | 109.5 |
O4—N3—C10 | 118.1 (3) | H6B—C6—H6C | 109.5 |
O3—N3—C10 | 118.7 (3) | C8—C7—C12 | 120.0 (3) |
N1—C1—O1 | 115.2 (3) | C8—C7—C1 | 119.8 (3) |
N1—C1—C7 | 127.6 (3) | C12—C7—C1 | 120.2 (3) |
O1—C1—C7 | 117.2 (3) | C9—C8—C7 | 120.2 (3) |
C4—C2—N1 | 129.6 (3) | C9—C8—H8 | 119.9 |
C4—C2—C3 | 120.5 (3) | C7—C8—H8 | 119.9 |
N1—C2—C3 | 109.9 (3) | C8—C9—C10 | 118.7 (3) |
O2—C3—O1 | 120.4 (3) | C8—C9—H9 | 120.7 |
O2—C3—C2 | 135.4 (3) | C10—C9—H9 | 120.7 |
O1—C3—C2 | 104.3 (2) | C11—C10—C9 | 122.7 (3) |
N2—C4—C2 | 131.3 (3) | C11—C10—N3 | 118.5 (3) |
N2—C4—H4 | 114.4 | C9—C10—N3 | 118.8 (3) |
C2—C4—H4 | 114.4 | C12—C11—C10 | 118.1 (3) |
N2—C5—H5A | 109.5 | C12—C11—H11 | 120.9 |
N2—C5—H5B | 109.5 | C10—C11—H11 | 120.9 |
H5A—C5—H5B | 109.5 | C11—C12—C7 | 120.4 (3) |
N2—C5—H5C | 109.5 | C11—C12—H12 | 119.8 |
H5A—C5—H5C | 109.5 | C7—C12—H12 | 119.8 |
C2—N1—C1—O1 | −0.3 (3) | O1—C1—C7—C8 | −179.8 (3) |
C2—N1—C1—C7 | 179.1 (3) | N1—C1—C7—C12 | −179.3 (3) |
C3—O1—C1—N1 | −0.1 (3) | O1—C1—C7—C12 | 0.1 (4) |
C3—O1—C1—C7 | −179.5 (3) | C12—C7—C8—C9 | 0.6 (5) |
C1—N1—C2—C4 | 178.8 (3) | C1—C7—C8—C9 | −179.5 (3) |
C1—N1—C2—C3 | 0.5 (3) | C7—C8—C9—C10 | −0.7 (5) |
C1—O1—C3—O2 | −178.9 (3) | C8—C9—C10—C11 | 0.4 (5) |
C1—O1—C3—C2 | 0.4 (3) | C8—C9—C10—N3 | 178.2 (3) |
C4—C2—C3—O2 | 0.1 (6) | O4—N3—C10—C11 | 172.7 (3) |
N1—C2—C3—O2 | 178.6 (4) | O3—N3—C10—C11 | −7.1 (4) |
C4—C2—C3—O1 | −179.1 (3) | O4—N3—C10—C9 | −5.1 (4) |
N1—C2—C3—O1 | −0.6 (3) | O3—N3—C10—C9 | 175.0 (3) |
C6—N2—C4—C2 | −178.4 (3) | C9—C10—C11—C12 | −0.1 (5) |
C5—N2—C4—C2 | −2.4 (5) | N3—C10—C11—C12 | −177.9 (3) |
N1—C2—C4—N2 | −3.9 (6) | C10—C11—C12—C7 | 0.1 (4) |
C3—C2—C4—N2 | 174.2 (3) | C8—C7—C12—C11 | −0.3 (4) |
N1—C1—C7—C8 | 0.9 (5) | C1—C7—C12—C11 | 179.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5c···N1 | 0.98 | 2.28 | 3.074 (5) | 137 |
C5—H5a···O2i | 0.98 | 2.53 | 3.504 (4) | 177 |
C5—H5c···O4ii | 0.98 | 2.57 | 3.259 (5) | 127 |
C9—H9···O1iii | 0.95 | 2.56 | 3.304 (4) | 135 |
C11—H11···O2iv | 0.95 | 2.45 | 3.144 (4) | 130 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+3/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C12H11N3O4 |
Mr | 261.24 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 9.5313 (2), 9.5204 (3), 13.0349 (4) |
β (°) | 106.661 (2) |
V (Å3) | 1133.15 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.42 × 0.38 × 0.22 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2007) |
Tmin, Tmax | 0.661, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14210, 2581, 2030 |
Rint | 0.071 |
(sin θ/λ)max (Å−1) | 0.647 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.220, 1.19 |
No. of reflections | 2581 |
No. of parameters | 176 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.30 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5c···N1 | 0.98 | 2.28 | 3.074 (5) | 137 |
C5—H5a···O2i | 0.98 | 2.53 | 3.504 (4) | 177 |
C5—H5c···O4ii | 0.98 | 2.57 | 3.259 (5) | 127 |
C9—H9···O1iii | 0.95 | 2.56 | 3.304 (4) | 135 |
C11—H11···O2iv | 0.95 | 2.45 | 3.144 (4) | 130 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+3/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2. |
The preparations of 4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-one derivatives have been reported using the Vilsmeier-Haack reactions (Meth-Cohn & Stanforth, 1991) of acylaminoacetanilides with POCl3 and DMF (Singh & Singh, 1994; Takahashi & Izawa, 2005; Singh et al., 1994; Kmetic & Stanovnik, 1995). The compounds have been used as precursors of 4-hydroxymethylene-2-aryl-2-oxazolin-5-one, which have been tested for anti-bacterial activities (Singh & Singh, 2008). The crystal structures of 4-(N,N-dimethylaminomethylene)-2-phenyl-2-oxazolin-5-one (Vasuki et al., 2002) and 4-(N,N-dimethylaminomethylene)-2-(2-nitrophenyl)-2-oxazolin-5-one (Vijayalakshmi et al., 1998) have been reported. We now report the crystal structure of 4-(N,N-dimethylaminomethylene)-2-(4-nitrophenyl)-2-oxazolin-5-one, (I).
The molecule of (I), Fig. 1, is essentially planar with the maximum deviations from the least-squares plane through all non-hydrogen atoms being 0.157 (4) Å for atom C5 and -0.158 (3) for atom O4; the r.m.s. = 0.068 Å. The sequence of C1–N1, N1–C2, C2–C4, and C4–N2 bond distances of 1.289 (4), 1.398 (4), 1.382 (5), and 1.317 (4) Å, respectively, indicate substantial delocalisation of π-electron density over these atoms. The geometric parameters in (I) match closely those found in the parent compound, namely 4-(N,N-dimethylaminomethylene)-2-phenyl-2-oxazolin-5-one (Vasuki et al., 2002) and in the 2-nitro derivative (Vijayalakshmi et al., 1998).
The crystal packing is dominated by C–H···O and π–π interactions; the N1 atom of the oxazolin-5-one is involved in an intramolecular C–H···N contact that shields this atom from forming intermolecular interactions, Table 1. Columns of molecules orientated along the b axis are stabilised by π–π contacts with the shortest of these occurring between centrosymmetrically related benzene rings [ring centroid(C7–C12)···ring centroid(C7–C12)i = 3.6312 (16) Å for i: 1-x, 1-y, 2-z]. The benzene rings also form π–π interactions with the oxazolin-5-one rings [ring centroid(C7–C12)···ring centroid(O1,N1,C1–C3)ii = 3.7645 (17) Å for ii: 1-x, -y, 2-z] to form a supramolecular chain, Fig. 2. The chains are connected by a series of C–H···O contacts, Table 1, to form a 3-D network, Fig. 3.