Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052378/at2183sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052378/at2183Isup2.hkl |
CCDC reference: 633592
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C15H12N2O4 | Z = 2 |
Mr = 284.27 | F(000) = 296 |
Triclinic, P1 | Dx = 1.513 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.3407 (4) Å | Cell parameters from 9747 reflections |
b = 10.4070 (8) Å | θ = 3.1–28.5° |
c = 12.0223 (9) Å | µ = 0.11 mm−1 |
α = 106.953 (6)° | T = 295 K |
β = 101.066 (6)° | Prism, colourless |
γ = 92.143 (6)° | 0.26 × 0.2 × 0.1 mm |
V = 624.18 (9) Å3 |
Stoe IPDS-II diffractometer | 2373 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ω scans | θmax = 28.5°, θmin = 3.1° |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | h = −6→7 |
Tmin = 0.972, Tmax = 0.989 | k = −13→13 |
9747 measured reflections | l = −16→16 |
3131 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0598P)2 + 0.095P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.114 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.34 e Å−3 |
3131 reflections | Δρmin = −0.19 e Å−3 |
203 parameters |
Experimental. IR (cm-1) (γ pyrone CO): 1671; 1H NMR (DMSO-d6, 400?MHz, γ, p.p.m.): 1.11 (t, 3H, –CH3), 3.48 (q, 2H, –CH2–), 6.42 (s, 1H, =CH), 7.52 (ddd, 1H, 6-H), 7.70 (d, 1H, j8,7 = 8.80 Hz, 8-H), 7.84 (ddd, 1H, 7-H), 8.11 (dd, 1H, j5,6= 8.40 Hz, j5,7= 1.60 Hz, 5-H), 8.74 (s, 1H, 2-H), 10.53 (s, 1H, NH), ESMS[ES (+), m/z]: 285 (M+1) |
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. |
x | y | z | Uiso*/Ueq | ||
O4 | 0.0983 (2) | 0.49490 (11) | −0.16132 (9) | 0.0264 (2) | |
H1 | 0.497 (4) | 0.1214 (18) | 0.4248 (17) | 0.027 (5)* | |
H10 | 0.179 (4) | 0.3843 (18) | 0.0156 (16) | 0.025 (4)* | |
H11 | 0.668 (4) | 0.2149 (19) | −0.1303 (17) | 0.032 (5)* | |
O1 | 0.3566 (2) | 0.23695 (10) | 0.27032 (9) | 0.0236 (2) | |
O2 | 0.7307 (2) | 0.14083 (11) | −0.00515 (9) | 0.0259 (2) | |
O3 | 0.6898 (2) | 0.25287 (11) | −0.33877 (9) | 0.0274 (2) | |
C5 | 0.6738 (3) | 0.11573 (13) | 0.17631 (12) | 0.0204 (3) | |
N2 | 0.3813 (2) | 0.39021 (12) | −0.27353 (11) | 0.0224 (3) | |
N1 | 0.5705 (2) | 0.27450 (12) | −0.15918 (11) | 0.0223 (3) | |
C13 | 0.5651 (3) | 0.29902 (14) | −0.26467 (13) | 0.0221 (3) | |
C7 | 0.6140 (3) | 0.17199 (13) | 0.07652 (12) | 0.0199 (3) | |
C12 | 0.2636 (3) | 0.41865 (14) | −0.17818 (12) | 0.0210 (3) | |
C8 | 0.4109 (3) | 0.26248 (13) | 0.08340 (12) | 0.0198 (3) | |
C9 | 0.2985 (3) | 0.28713 (14) | 0.17874 (12) | 0.0216 (3) | |
H9 | 0.1686 | 0.3443 | 0.1807 | 0.026* | |
C14 | 0.3221 (3) | 0.44218 (15) | −0.37468 (13) | 0.0246 (3) | |
H14A | 0.4775 | 0.4531 | −0.4029 | 0.03* | |
H14B | 0.2606 | 0.5303 | −0.3492 | 0.03* | |
C15 | 0.1211 (3) | 0.34943 (15) | −0.47615 (13) | 0.0272 (3) | |
H15A | 0.178 | 0.261 | −0.4996 | 0.041* | |
H15B | 0.0955 | 0.3846 | −0.5425 | 0.041* | |
H15C | −0.0375 | 0.3441 | −0.4505 | 0.041* | |
C1 | 0.5904 (3) | 0.09625 (15) | 0.36340 (13) | 0.0253 (3) | |
C11 | 0.3856 (3) | 0.33805 (13) | −0.10197 (12) | 0.0203 (3) | |
C10 | 0.3145 (3) | 0.33350 (14) | −0.00244 (12) | 0.0206 (3) | |
C6 | 0.5421 (3) | 0.14943 (14) | 0.26884 (13) | 0.0213 (3) | |
C2 | 0.7731 (3) | 0.00679 (15) | 0.36424 (13) | 0.0263 (3) | |
H2 | 0.8067 | −0.0305 | 0.4264 | 0.032* | |
C4 | 0.8606 (3) | 0.02510 (14) | 0.18031 (13) | 0.0236 (3) | |
H4 | 0.9519 | 0.0014 | 0.12 | 0.028* | |
C3 | 0.9093 (3) | −0.02900 (15) | 0.27333 (14) | 0.0264 (3) | |
H3 | 1.0329 | −0.0893 | 0.2755 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0252 (5) | 0.0283 (5) | 0.0287 (5) | 0.0126 (4) | 0.0074 (4) | 0.0109 (4) |
O1 | 0.0237 (5) | 0.0279 (5) | 0.0244 (5) | 0.0100 (4) | 0.0089 (4) | 0.0124 (4) |
O2 | 0.0266 (5) | 0.0316 (5) | 0.0255 (5) | 0.0141 (4) | 0.0116 (4) | 0.0127 (4) |
O3 | 0.0295 (6) | 0.0327 (5) | 0.0263 (5) | 0.0120 (4) | 0.0130 (4) | 0.0130 (4) |
C5 | 0.0189 (6) | 0.0185 (6) | 0.0235 (6) | 0.0042 (5) | 0.0028 (5) | 0.0067 (5) |
N2 | 0.0249 (6) | 0.0230 (6) | 0.0222 (6) | 0.0084 (5) | 0.0057 (5) | 0.0103 (5) |
N1 | 0.0223 (6) | 0.0261 (6) | 0.0231 (6) | 0.0108 (5) | 0.0085 (5) | 0.0111 (5) |
C13 | 0.0214 (7) | 0.0233 (6) | 0.0231 (6) | 0.0053 (5) | 0.0053 (5) | 0.0089 (5) |
C7 | 0.0183 (6) | 0.0190 (6) | 0.0217 (6) | 0.0040 (5) | 0.0031 (5) | 0.0058 (5) |
C12 | 0.0213 (7) | 0.0203 (6) | 0.0219 (6) | 0.0051 (5) | 0.0047 (5) | 0.0070 (5) |
C8 | 0.0197 (7) | 0.0196 (6) | 0.0207 (6) | 0.0041 (5) | 0.0043 (5) | 0.0065 (5) |
C9 | 0.0205 (7) | 0.0219 (6) | 0.0247 (7) | 0.0072 (5) | 0.0066 (5) | 0.0090 (5) |
C14 | 0.0256 (7) | 0.0280 (7) | 0.0255 (7) | 0.0075 (6) | 0.0065 (6) | 0.0148 (6) |
C15 | 0.0290 (8) | 0.0298 (7) | 0.0242 (7) | 0.0087 (6) | 0.0062 (6) | 0.0092 (6) |
C1 | 0.0253 (7) | 0.0288 (7) | 0.0243 (7) | 0.0039 (6) | 0.0068 (6) | 0.0108 (6) |
C11 | 0.0190 (6) | 0.0193 (6) | 0.0226 (6) | 0.0057 (5) | 0.0047 (5) | 0.0058 (5) |
C10 | 0.0194 (6) | 0.0198 (6) | 0.0230 (6) | 0.0061 (5) | 0.0054 (5) | 0.0059 (5) |
C6 | 0.0194 (6) | 0.0200 (6) | 0.0243 (7) | 0.0046 (5) | 0.0037 (5) | 0.0067 (5) |
C2 | 0.0262 (7) | 0.0267 (7) | 0.0271 (7) | 0.0016 (6) | −0.0001 (6) | 0.0137 (6) |
C4 | 0.0224 (7) | 0.0220 (6) | 0.0263 (7) | 0.0055 (5) | 0.0041 (5) | 0.0075 (5) |
C3 | 0.0240 (7) | 0.0229 (7) | 0.0318 (7) | 0.0070 (5) | 0.0013 (6) | 0.0100 (6) |
O4—C12 | 1.2151 (17) | C9—H9 | 0.93 |
O1—C9 | 1.3407 (17) | C14—C15 | 1.518 (2) |
O1—C6 | 1.3698 (16) | C14—H14A | 0.97 |
O2—C7 | 1.2336 (17) | C14—H14B | 0.97 |
O3—C13 | 1.2121 (18) | C15—H15A | 0.96 |
C5—C6 | 1.395 (2) | C15—H15B | 0.96 |
C5—C4 | 1.4018 (19) | C15—H15C | 0.96 |
C5—C7 | 1.4699 (19) | C1—C2 | 1.374 (2) |
N2—C12 | 1.3747 (18) | C1—C6 | 1.389 (2) |
N2—C13 | 1.4016 (18) | C1—H1 | 0.949 (19) |
N2—C14 | 1.4560 (17) | C11—C10 | 1.336 (2) |
N1—C13 | 1.3600 (19) | C10—H10 | 0.936 (19) |
N1—C11 | 1.3896 (18) | C2—C3 | 1.397 (2) |
N1—H11 | 0.92 (2) | C2—H2 | 0.93 |
C7—C8 | 1.4614 (19) | C4—C3 | 1.379 (2) |
C12—C11 | 1.4925 (19) | C4—H4 | 0.93 |
C8—C9 | 1.358 (2) | C3—H3 | 0.93 |
C8—C10 | 1.4647 (18) | ||
C9—O1—C6 | 118.46 (11) | C15—C14—H14B | 109.2 |
C6—C5—C4 | 118.13 (13) | H14A—C14—H14B | 107.9 |
C6—C5—C7 | 120.66 (12) | C14—C15—H15A | 109.5 |
C4—C5—C7 | 121.19 (13) | C14—C15—H15B | 109.5 |
C12—N2—C13 | 111.45 (11) | H15A—C15—H15B | 109.5 |
C12—N2—C14 | 125.83 (12) | C14—C15—H15C | 109.5 |
C13—N2—C14 | 122.69 (12) | H15A—C15—H15C | 109.5 |
C13—N1—C11 | 112.00 (12) | H15B—C15—H15C | 109.5 |
C13—N1—H11 | 126.4 (12) | C2—C1—C6 | 118.26 (14) |
C11—N1—H11 | 121.1 (12) | C2—C1—H1 | 121.9 (11) |
O3—C13—N1 | 128.53 (13) | C6—C1—H1 | 119.9 (11) |
O3—C13—N2 | 125.16 (13) | C10—C11—N1 | 131.50 (13) |
N1—C13—N2 | 106.31 (12) | C10—C11—C12 | 123.50 (13) |
O2—C7—C8 | 125.01 (13) | N1—C11—C12 | 104.99 (12) |
O2—C7—C5 | 120.08 (12) | C11—C10—C8 | 131.40 (13) |
C8—C7—C5 | 114.90 (12) | C11—C10—H10 | 114.4 (11) |
O4—C12—N2 | 126.19 (13) | C8—C10—H10 | 114.2 (11) |
O4—C12—C11 | 128.72 (13) | O1—C6—C1 | 116.61 (13) |
N2—C12—C11 | 105.08 (11) | O1—C6—C5 | 121.19 (12) |
C9—C8—C7 | 118.48 (12) | C1—C6—C5 | 122.20 (13) |
C9—C8—C10 | 114.92 (12) | C1—C2—C3 | 121.13 (14) |
C7—C8—C10 | 126.59 (12) | C1—C2—H2 | 119.4 |
O1—C9—C8 | 126.29 (13) | C3—C2—H2 | 119.4 |
O1—C9—H9 | 116.9 | C3—C4—C5 | 120.24 (14) |
C8—C9—H9 | 116.9 | C3—C4—H4 | 119.9 |
N2—C14—C15 | 112.24 (12) | C5—C4—H4 | 119.9 |
N2—C14—H14A | 109.2 | C4—C3—C2 | 120.02 (14) |
C15—C14—H14A | 109.2 | C4—C3—H3 | 120 |
N2—C14—H14B | 109.2 | C2—C3—H3 | 120 |
C11—N1—C13—O3 | −175.36 (15) | C13—N1—C11—C10 | 174.91 (15) |
C11—N1—C13—N2 | 4.25 (16) | C13—N1—C11—C12 | −4.09 (16) |
C12—N2—C13—O3 | 176.97 (14) | O4—C12—C11—C10 | 4.0 (2) |
C14—N2—C13—O3 | −1.0 (2) | N2—C12—C11—C10 | −176.84 (13) |
C12—N2—C13—N1 | −2.66 (16) | O4—C12—C11—N1 | −176.87 (14) |
C14—N2—C13—N1 | 179.33 (13) | N2—C12—C11—N1 | 2.26 (14) |
C6—C5—C7—O2 | −179.56 (13) | N1—C11—C10—C8 | 1.8 (3) |
C4—C5—C7—O2 | −0.8 (2) | C12—C11—C10—C8 | −179.37 (14) |
C6—C5—C7—C8 | −0.20 (19) | C9—C8—C10—C11 | 176.85 (15) |
C4—C5—C7—C8 | 178.60 (12) | C7—C8—C10—C11 | −2.1 (2) |
C13—N2—C12—O4 | 179.37 (14) | C9—O1—C6—C1 | −177.89 (13) |
C14—N2—C12—O4 | −2.7 (2) | C9—O1—C6—C5 | 1.85 (19) |
C13—N2—C12—C11 | 0.20 (15) | C2—C1—C6—O1 | 179.24 (12) |
C14—N2—C12—C11 | 178.14 (13) | C2—C1—C6—C5 | −0.5 (2) |
O2—C7—C8—C9 | 179.70 (14) | C4—C5—C6—O1 | −179.76 (12) |
C5—C7—C8—C9 | 0.38 (18) | C7—C5—C6—O1 | −0.9 (2) |
O2—C7—C8—C10 | −1.4 (2) | C4—C5—C6—C1 | 0.0 (2) |
C5—C7—C8—C10 | 179.30 (13) | C7—C5—C6—C1 | 178.80 (13) |
C6—O1—C9—C8 | −1.7 (2) | C6—C1—C2—C3 | 0.7 (2) |
C7—C8—C9—O1 | 0.6 (2) | C6—C5—C4—C3 | 0.4 (2) |
C10—C8—C9—O1 | −178.44 (13) | C7—C5—C4—C3 | −178.43 (13) |
C12—N2—C14—C15 | −91.48 (17) | C5—C4—C3—C2 | −0.2 (2) |
C13—N2—C14—C15 | 86.24 (17) | C1—C2—C3—C4 | −0.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O2 | 0.93 (2) | 1.86 (2) | 2.6607 (17) | 142.9 (18) |
C10—H10···O4 | 0.93 (2) | 2.674 (19) | 2.995 (2) | 101.0 (13) |