Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703200X/hb2470sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680703200X/hb2470Isup2.hkl |
CCDC reference: 658983
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.144
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C9 .. 6.51 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.14 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.31
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 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of 4-methoxybenzaldehyde (1.36 g, 10 mmol) and methyl hydrazinocarboxylate (0.90 g, 10 mmol) was refluxed in ethanol (30 ml) and monitored by thin-layer chromatography. After the reaction was complete, the resulting solid was filtered off and washed with a little cool methanol. 50 mg of (I) was dissolved in 20 ml e thanol and the solution was kept at room temperature for 10 d; natural evaporation gave colourless prisms of (I) suitable for X-ray analysis.
The N-bound H atoms were located in a difference map and their positions and Uiso values were freely refined.
The C-bound H atoms were positioned geometrically, with C—H = 0.93–0.96Å and refined in a riding-model approximation, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Symmetrical and unsymmetrical 1,3,4-oxadiazoles have been reported to be versatile compounds with many properties (Omar et al., 1996; Goswami et al., 1984; Tully et al., 1991; Borg et al., 1999). The most common synthetic approach to 1,3,4-oxadiazoles involves oxidative cyclization from the corresponding aldehyde N-acylhydrazones (Yang & Dai, 1993; Shang, 2006). The title compound, (I), as the oxidative precursor, was synthesized from 4-methoxybenzaldehyde and methyl hydrazinocarboxylate in ethanol under reflux.
Both asymmetric molecules of (I) adopt a trans configuration with respect to the C=N bond (Fig. 1) as discribed previously (Shang et al., 2007). The crystal structure is stabilized mainly through intermolecular N—H··· O hydrogen bonds (Table 1).
For related literature, see: Borg et al. (1999); Goswami et al. (1984); Omar et al. (1996); Shang (2006); Shang et al. (2007); Tully et al. (1991); Yang & Dai (1993).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of (I), drawn with 50% probability ellipsoids (arbitrary spheres for the H atoms). | |
Fig. 2. Reaction scheme for the formation of the title compound. |
C10H12N2O3 | Z = 4 |
Mr = 208.22 | F(000) = 440 |
Triclinic, P1 | Dx = 1.325 Mg m−3 |
Hall symbol: -P 1 | Melting point = 464–466 K |
a = 7.3738 (16) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.671 (2) Å | Cell parameters from 1471 reflections |
c = 14.689 (3) Å | θ = 2.5–24.6° |
α = 89.128 (4)° | µ = 0.10 mm−1 |
β = 85.961 (4)° | T = 293 K |
γ = 87.693 (4)° | Prism, colorless |
V = 1044.0 (4) Å3 | 0.30 × 0.20 × 0.16 mm |
Bruker SMART CCD diffractometer | 3674 independent reflections |
Radiation source: fine-focus sealed tube | 2083 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −8→8 |
Tmin = 0.971, Tmax = 0.984 | k = −9→11 |
5411 measured reflections | l = −12→17 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0721P)2 + 0.0669P] where P = (Fo2 + 2Fc2)/3 |
3674 reflections | (Δ/σ)max = 0.001 |
283 parameters | Δρmax = 0.17 e Å−3 |
7 restraints | Δρmin = −0.18 e Å−3 |
C10H12N2O3 | γ = 87.693 (4)° |
Mr = 208.22 | V = 1044.0 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.3738 (16) Å | Mo Kα radiation |
b = 9.671 (2) Å | µ = 0.10 mm−1 |
c = 14.689 (3) Å | T = 293 K |
α = 89.128 (4)° | 0.30 × 0.20 × 0.16 mm |
β = 85.961 (4)° |
Bruker SMART CCD diffractometer | 3674 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 2083 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.984 | Rint = 0.025 |
5411 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 7 restraints |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.17 e Å−3 |
3674 reflections | Δρmin = −0.18 e Å−3 |
283 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.0466 (3) | 0.72191 (18) | −0.27347 (12) | 0.0742 (6) | |
O2 | 0.4251 (3) | 0.72508 (15) | 0.24793 (12) | 0.0739 (6) | |
O3 | 0.3898 (3) | 0.92926 (15) | 0.32026 (11) | 0.0672 (5) | |
O4 | 0.1151 (3) | 0.22590 (17) | 0.70570 (12) | 0.0740 (6) | |
O5 | 0.6009 (2) | 0.21963 (15) | 0.15450 (11) | 0.0613 (5) | |
O6 | 0.6331 (2) | 0.42596 (15) | 0.08266 (11) | 0.0609 (5) | |
N1 | 0.6155 (3) | 0.85722 (18) | 0.10837 (13) | 0.0511 (5) | |
N2 | 0.5379 (3) | 0.92379 (19) | 0.18515 (14) | 0.0543 (5) | |
N3 | 0.4456 (3) | 0.35778 (19) | 0.30239 (13) | 0.0538 (5) | |
N4 | 0.5092 (3) | 0.42285 (19) | 0.22325 (14) | 0.0554 (6) | |
C1 | 1.1315 (5) | 0.8106 (3) | −0.34000 (18) | 0.0860 (9) | |
H1A | 1.0423 | 0.8755 | −0.3620 | 0.129* | |
H1B | 1.1851 | 0.7565 | −0.3899 | 0.129* | |
H1C | 1.2243 | 0.8598 | −0.3131 | 0.129* | |
C2 | 0.9621 (3) | 0.7807 (2) | −0.19683 (17) | 0.0553 (6) | |
C3 | 0.8874 (4) | 0.6903 (2) | −0.13273 (18) | 0.0636 (7) | |
H3 | 0.8954 | 0.5958 | −0.1440 | 0.076* | |
C4 | 0.8010 (3) | 0.7373 (2) | −0.05229 (17) | 0.0573 (7) | |
H4 | 0.7531 | 0.6744 | −0.0094 | 0.069* | |
C5 | 0.7851 (3) | 0.8790 (2) | −0.03477 (16) | 0.0486 (6) | |
C6 | 0.8608 (4) | 0.9673 (2) | −0.10001 (17) | 0.0598 (7) | |
H6 | 0.8516 | 1.0620 | −0.0895 | 0.072* | |
C7 | 0.9497 (4) | 0.9210 (2) | −0.18051 (17) | 0.0615 (7) | |
H7 | 1.0004 | 0.9834 | −0.2229 | 0.074* | |
C8 | 0.6944 (3) | 0.9342 (2) | 0.04870 (16) | 0.0511 (6) | |
H8 | 0.6943 | 1.0289 | 0.0586 | 0.061* | |
C9 | 0.4497 (4) | 0.8480 (2) | 0.24991 (17) | 0.0543 (6) | |
C10 | 0.2883 (4) | 0.8629 (3) | 0.39364 (19) | 0.0823 (9) | |
H10A | 0.1935 | 0.8119 | 0.3699 | 0.123* | |
H10B | 0.2354 | 0.9315 | 0.4351 | 0.123* | |
H10C | 0.3677 | 0.8008 | 0.4253 | 0.123* | |
C11 | 0.0553 (4) | 0.3160 (3) | 0.77846 (17) | 0.0767 (8) | |
H11A | 0.1506 | 0.3770 | 0.7898 | 0.115* | |
H11B | 0.0253 | 0.2623 | 0.8325 | 0.115* | |
H11C | −0.0503 | 0.3696 | 0.7621 | 0.115* | |
C12 | 0.1746 (3) | 0.2837 (2) | 0.62447 (17) | 0.0555 (6) | |
C13 | 0.1735 (4) | 0.4221 (3) | 0.60634 (18) | 0.0778 (9) | |
H13 | 0.1303 | 0.4850 | 0.6508 | 0.093* | |
C14 | 0.2377 (5) | 0.4679 (3) | 0.52072 (19) | 0.0879 (10) | |
H14 | 0.2366 | 0.5627 | 0.5090 | 0.105* | |
C15 | 0.3028 (3) | 0.3802 (2) | 0.45221 (16) | 0.0545 (6) | |
C16 | 0.3010 (4) | 0.2401 (3) | 0.47233 (18) | 0.0685 (8) | |
H16 | 0.3434 | 0.1766 | 0.4281 | 0.082* | |
C17 | 0.2375 (4) | 0.1938 (3) | 0.55668 (19) | 0.0776 (9) | |
H17 | 0.2369 | 0.0991 | 0.5685 | 0.093* | |
C18 | 0.3728 (4) | 0.4349 (2) | 0.36433 (16) | 0.0616 (7) | |
H18 | 0.3635 | 0.5298 | 0.3535 | 0.074* | |
C19 | 0.5820 (3) | 0.3447 (2) | 0.15391 (16) | 0.0486 (6) | |
C20 | 0.7034 (4) | 0.3552 (3) | 0.00160 (17) | 0.0682 (8) | |
H20A | 0.8084 | 0.2986 | 0.0149 | 0.102* | |
H20B | 0.7369 | 0.4218 | −0.0451 | 0.102* | |
H20C | 0.6118 | 0.2978 | −0.0192 | 0.102* | |
H2A | 0.543 (3) | 1.0150 (11) | 0.1909 (16) | 0.073 (8)* | |
H4A | 0.496 (3) | 0.5137 (11) | 0.2144 (17) | 0.075 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0931 (15) | 0.0597 (11) | 0.0668 (12) | 0.0012 (10) | 0.0165 (11) | −0.0158 (10) |
O2 | 0.1020 (15) | 0.0338 (9) | 0.0830 (13) | −0.0088 (9) | 0.0193 (11) | −0.0066 (9) |
O3 | 0.0990 (15) | 0.0413 (9) | 0.0585 (11) | −0.0052 (9) | 0.0160 (10) | −0.0047 (8) |
O4 | 0.1010 (15) | 0.0564 (11) | 0.0617 (11) | −0.0050 (10) | 0.0148 (10) | 0.0021 (9) |
O5 | 0.0861 (13) | 0.0310 (9) | 0.0655 (11) | 0.0002 (8) | 0.0045 (9) | −0.0051 (7) |
O6 | 0.0915 (14) | 0.0356 (9) | 0.0533 (10) | −0.0021 (8) | 0.0115 (9) | −0.0037 (8) |
N1 | 0.0595 (13) | 0.0370 (10) | 0.0559 (12) | 0.0019 (9) | 0.0018 (10) | −0.0079 (10) |
N2 | 0.0738 (15) | 0.0313 (10) | 0.0558 (13) | −0.0009 (10) | 0.0090 (11) | −0.0035 (10) |
N3 | 0.0657 (14) | 0.0406 (10) | 0.0544 (12) | −0.0047 (10) | 0.0022 (11) | −0.0034 (10) |
N4 | 0.0786 (16) | 0.0330 (11) | 0.0526 (12) | −0.0011 (10) | 0.0099 (11) | −0.0041 (10) |
C1 | 0.119 (3) | 0.077 (2) | 0.0587 (17) | 0.0095 (18) | 0.0152 (18) | −0.0035 (16) |
C2 | 0.0609 (17) | 0.0481 (14) | 0.0563 (15) | 0.0027 (12) | −0.0006 (13) | −0.0108 (12) |
C3 | 0.0767 (19) | 0.0371 (13) | 0.0752 (18) | −0.0018 (12) | 0.0103 (15) | −0.0145 (13) |
C4 | 0.0639 (17) | 0.0406 (13) | 0.0663 (17) | −0.0026 (12) | 0.0065 (13) | −0.0069 (12) |
C5 | 0.0526 (15) | 0.0370 (12) | 0.0564 (15) | −0.0008 (10) | −0.0041 (12) | −0.0089 (11) |
C6 | 0.0780 (19) | 0.0373 (12) | 0.0627 (16) | 0.0030 (12) | 0.0044 (14) | −0.0096 (12) |
C7 | 0.079 (2) | 0.0458 (14) | 0.0581 (16) | −0.0003 (13) | 0.0046 (14) | −0.0001 (12) |
C8 | 0.0645 (17) | 0.0321 (11) | 0.0563 (15) | −0.0022 (11) | 0.0001 (13) | −0.0065 (11) |
C9 | 0.0671 (18) | 0.0345 (13) | 0.0608 (16) | 0.0027 (11) | −0.0032 (13) | −0.0060 (12) |
C10 | 0.106 (2) | 0.0636 (17) | 0.0737 (19) | −0.0154 (16) | 0.0278 (17) | −0.0073 (15) |
C11 | 0.096 (2) | 0.0724 (18) | 0.0594 (17) | −0.0045 (16) | 0.0120 (16) | −0.0027 (15) |
C12 | 0.0641 (17) | 0.0472 (14) | 0.0548 (15) | −0.0070 (12) | 0.0001 (13) | 0.0012 (12) |
C13 | 0.122 (3) | 0.0487 (16) | 0.0600 (17) | −0.0051 (16) | 0.0165 (17) | −0.0069 (13) |
C14 | 0.149 (3) | 0.0395 (15) | 0.0697 (19) | 0.0006 (16) | 0.028 (2) | 0.0000 (14) |
C15 | 0.0658 (18) | 0.0406 (13) | 0.0562 (15) | −0.0022 (11) | 0.0026 (13) | −0.0030 (11) |
C16 | 0.092 (2) | 0.0434 (14) | 0.0676 (18) | −0.0036 (13) | 0.0160 (16) | −0.0083 (13) |
C17 | 0.112 (3) | 0.0397 (14) | 0.077 (2) | −0.0070 (14) | 0.0239 (18) | −0.0012 (14) |
C18 | 0.090 (2) | 0.0355 (13) | 0.0578 (16) | 0.0018 (13) | 0.0055 (15) | −0.0027 (12) |
C19 | 0.0584 (17) | 0.0338 (12) | 0.0539 (15) | −0.0036 (11) | −0.0030 (12) | −0.0043 (11) |
C20 | 0.093 (2) | 0.0529 (15) | 0.0558 (16) | 0.0003 (14) | 0.0123 (15) | −0.0101 (13) |
O1—C2 | 1.368 (3) | C5—C6 | 1.377 (3) |
O1—C1 | 1.419 (3) | C5—C8 | 1.453 (3) |
O2—C9 | 1.211 (3) | C6—C7 | 1.383 (3) |
O3—C9 | 1.347 (3) | C6—H6 | 0.9300 |
O3—C10 | 1.427 (3) | C7—H7 | 0.9300 |
O4—C12 | 1.361 (3) | C8—H8 | 0.9300 |
O4—C11 | 1.424 (3) | C10—H10A | 0.9600 |
O5—C19 | 1.212 (2) | C10—H10B | 0.9600 |
O6—C19 | 1.341 (3) | C10—H10C | 0.9600 |
O6—C20 | 1.437 (3) | C11—H11A | 0.9600 |
N1—C8 | 1.266 (3) | C11—H11B | 0.9600 |
N1—N2 | 1.384 (3) | C11—H11C | 0.9600 |
N2—C9 | 1.340 (3) | C12—C13 | 1.361 (3) |
N2—H2A | 0.889 (10) | C12—C17 | 1.375 (3) |
N3—C18 | 1.262 (3) | C13—C14 | 1.385 (4) |
N3—N4 | 1.375 (3) | C13—H13 | 0.9300 |
N4—C19 | 1.346 (3) | C14—C15 | 1.373 (3) |
N4—H4A | 0.889 (10) | C14—H14 | 0.9300 |
C1—H1A | 0.9600 | C15—C16 | 1.383 (3) |
C1—H1B | 0.9600 | C15—C18 | 1.456 (3) |
C1—H1C | 0.9600 | C16—C17 | 1.368 (3) |
C2—C3 | 1.376 (3) | C16—H16 | 0.9300 |
C2—C7 | 1.380 (3) | C17—H17 | 0.9300 |
C3—C4 | 1.376 (3) | C18—H18 | 0.9300 |
C3—H3 | 0.9300 | C20—H20A | 0.9600 |
C4—C5 | 1.397 (3) | C20—H20B | 0.9600 |
C4—H4 | 0.9300 | C20—H20C | 0.9600 |
C2—O1—C1 | 118.0 (2) | O3—C10—H10A | 109.5 |
C9—O3—C10 | 116.03 (19) | O3—C10—H10B | 109.5 |
C12—O4—C11 | 118.09 (19) | H10A—C10—H10B | 109.5 |
C19—O6—C20 | 115.72 (17) | O3—C10—H10C | 109.5 |
C8—N1—N2 | 115.66 (18) | H10A—C10—H10C | 109.5 |
C9—N2—N1 | 118.34 (19) | H10B—C10—H10C | 109.5 |
C9—N2—H2A | 120.4 (17) | O4—C11—H11A | 109.5 |
N1—N2—H2A | 121.3 (17) | O4—C11—H11B | 109.5 |
C18—N3—N4 | 116.34 (19) | H11A—C11—H11B | 109.5 |
C19—N4—N3 | 118.58 (19) | O4—C11—H11C | 109.5 |
C19—N4—H4A | 118.6 (17) | H11A—C11—H11C | 109.5 |
N3—N4—H4A | 122.7 (17) | H11B—C11—H11C | 109.5 |
O1—C1—H1A | 109.5 | C13—C12—O4 | 124.6 (2) |
O1—C1—H1B | 109.5 | C13—C12—C17 | 118.8 (2) |
H1A—C1—H1B | 109.5 | O4—C12—C17 | 116.6 (2) |
O1—C1—H1C | 109.5 | C12—C13—C14 | 119.0 (3) |
H1A—C1—H1C | 109.5 | C12—C13—H13 | 120.5 |
H1B—C1—H1C | 109.5 | C14—C13—H13 | 120.5 |
O1—C2—C3 | 116.0 (2) | C15—C14—C13 | 123.3 (2) |
O1—C2—C7 | 124.5 (2) | C15—C14—H14 | 118.4 |
C3—C2—C7 | 119.5 (2) | C13—C14—H14 | 118.4 |
C2—C3—C4 | 121.2 (2) | C14—C15—C16 | 116.5 (2) |
C2—C3—H3 | 119.4 | C14—C15—C18 | 120.7 (2) |
C4—C3—H3 | 119.4 | C16—C15—C18 | 122.8 (2) |
C3—C4—C5 | 120.2 (2) | C17—C16—C15 | 120.7 (2) |
C3—C4—H4 | 119.9 | C17—C16—H16 | 119.7 |
C5—C4—H4 | 119.9 | C15—C16—H16 | 119.7 |
C6—C5—C4 | 117.4 (2) | C16—C17—C12 | 121.8 (2) |
C6—C5—C8 | 120.0 (2) | C16—C17—H17 | 119.1 |
C4—C5—C8 | 122.5 (2) | C12—C17—H17 | 119.1 |
C5—C6—C7 | 122.7 (2) | N3—C18—C15 | 122.2 (2) |
C5—C6—H6 | 118.6 | N3—C18—H18 | 118.9 |
C7—C6—H6 | 118.6 | C15—C18—H18 | 118.9 |
C2—C7—C6 | 118.8 (2) | O5—C19—O6 | 124.1 (2) |
C2—C7—H7 | 120.6 | O5—C19—N4 | 126.0 (2) |
C6—C7—H7 | 120.6 | O6—C19—N4 | 109.86 (19) |
N1—C8—C5 | 122.0 (2) | O6—C20—H20A | 109.5 |
N1—C8—H8 | 119.0 | O6—C20—H20B | 109.5 |
C5—C8—H8 | 119.0 | H20A—C20—H20B | 109.5 |
O2—C9—N2 | 126.7 (2) | O6—C20—H20C | 109.5 |
O2—C9—O3 | 123.5 (2) | H20A—C20—H20C | 109.5 |
N2—C9—O3 | 109.78 (19) | H20B—C20—H20C | 109.5 |
C8—N1—N2—C9 | 178.8 (2) | C10—O3—C9—N2 | 178.3 (2) |
C18—N3—N4—C19 | −177.6 (2) | C11—O4—C12—C13 | −3.1 (4) |
C1—O1—C2—C3 | −177.7 (2) | C11—O4—C12—C17 | 177.7 (2) |
C1—O1—C2—C7 | 1.6 (4) | O4—C12—C13—C14 | −179.9 (3) |
O1—C2—C3—C4 | 179.1 (2) | C17—C12—C13—C14 | −0.7 (4) |
C7—C2—C3—C4 | −0.3 (4) | C12—C13—C14—C15 | 0.1 (5) |
C2—C3—C4—C5 | 1.0 (4) | C13—C14—C15—C16 | 0.4 (5) |
C3—C4—C5—C6 | −0.9 (4) | C13—C14—C15—C18 | −178.4 (3) |
C3—C4—C5—C8 | 179.6 (2) | C14—C15—C16—C17 | −0.2 (4) |
C4—C5—C6—C7 | 0.1 (4) | C18—C15—C16—C17 | 178.6 (3) |
C8—C5—C6—C7 | 179.6 (2) | C15—C16—C17—C12 | −0.4 (5) |
O1—C2—C7—C6 | −179.9 (2) | C13—C12—C17—C16 | 0.9 (5) |
C3—C2—C7—C6 | −0.5 (4) | O4—C12—C17—C16 | −179.8 (2) |
C5—C6—C7—C2 | 0.6 (4) | N4—N3—C18—C15 | −178.8 (2) |
N2—N1—C8—C5 | 178.8 (2) | C14—C15—C18—N3 | 174.7 (3) |
C6—C5—C8—N1 | 176.5 (2) | C16—C15—C18—N3 | −4.0 (4) |
C4—C5—C8—N1 | −4.0 (4) | C20—O6—C19—O5 | 4.0 (3) |
N1—N2—C9—O2 | −2.2 (4) | C20—O6—C19—N4 | −176.4 (2) |
N1—N2—C9—O3 | 177.75 (19) | N3—N4—C19—O5 | −1.4 (4) |
C10—O3—C9—O2 | −1.8 (4) | N3—N4—C19—O6 | 178.99 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O5i | 0.89 (1) | 2.10 (1) | 2.940 (2) | 158 (2) |
N4—H4A···O2 | 0.89 (1) | 2.15 (1) | 2.986 (2) | 157 (2) |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C10H12N2O3 |
Mr | 208.22 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.3738 (16), 9.671 (2), 14.689 (3) |
α, β, γ (°) | 89.128 (4), 85.961 (4), 87.693 (4) |
V (Å3) | 1044.0 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.30 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.971, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5411, 3674, 2083 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.144, 1.00 |
No. of reflections | 3674 |
No. of parameters | 283 |
No. of restraints | 7 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.18 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O5i | 0.889 (10) | 2.096 (13) | 2.940 (2) | 158 (2) |
N4—H4A···O2 | 0.889 (10) | 2.145 (14) | 2.986 (2) | 157 (2) |
Symmetry code: (i) x, y+1, z. |
Symmetrical and unsymmetrical 1,3,4-oxadiazoles have been reported to be versatile compounds with many properties (Omar et al., 1996; Goswami et al., 1984; Tully et al., 1991; Borg et al., 1999). The most common synthetic approach to 1,3,4-oxadiazoles involves oxidative cyclization from the corresponding aldehyde N-acylhydrazones (Yang & Dai, 1993; Shang, 2006). The title compound, (I), as the oxidative precursor, was synthesized from 4-methoxybenzaldehyde and methyl hydrazinocarboxylate in ethanol under reflux.
Both asymmetric molecules of (I) adopt a trans configuration with respect to the C=N bond (Fig. 1) as discribed previously (Shang et al., 2007). The crystal structure is stabilized mainly through intermolecular N—H··· O hydrogen bonds (Table 1).