In the title compound, C
13H
12O
5, the ethoxycarbonyl group makes an angle of 60.73 (4)° with the coumarin ring system. There are intermolecular π–π and C—H
π interactions.
Supporting information
CCDC reference: 610860
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.044
- wR factor = 0.148
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. O3 .. 2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. O5 .. 2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. O4 .. 2.72 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 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
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.
Ethyl 8-methoxy-2-oxo-2
H-1-benzopyran-3-carboxylate
top
Crystal data top
C13H12O5 | F(000) = 520.00 |
Mr = 248.23 | Dx = 1.454 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54187 Å |
Hall symbol: -P 2yn | Cell parameters from 14368 reflections |
a = 6.8572 (14) Å | θ = 4.2–68.2° |
b = 10.644 (2) Å | µ = 0.95 mm−1 |
c = 15.780 (3) Å | T = 173 K |
β = 100.153 (14)° | Prism, colorless |
V = 1133.6 (4) Å3 | 0.40 × 0.30 × 0.25 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1860 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.027 |
ω scans | θmax = 68.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −8→8 |
Tmin = 0.608, Tmax = 0.788 | k = −12→12 |
14613 measured reflections | l = −18→18 |
2061 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.044 | w = 4Fo2/[0.0041Fo2 + σ(Fo2) |
wR(F2) = 0.148 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.32 e Å−3 |
2061 reflections | Δρmin = −0.50 e Å−3 |
175 parameters | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.79794 (13) | 0.15692 (8) | 0.46548 (6) | 0.0223 (2) | |
O2 | 0.79140 (16) | 0.28452 (9) | 0.35466 (6) | 0.0340 (2) | |
O3 | 0.81319 (14) | 0.13218 (12) | 0.19016 (6) | 0.0399 (3) | |
O4 | 0.50483 (12) | 0.05925 (9) | 0.19045 (5) | 0.0257 (2) | |
O5 | 0.84569 (14) | 0.13967 (9) | 0.63348 (6) | 0.0271 (2) | |
C1 | 0.77138 (18) | 0.17849 (12) | 0.37797 (8) | 0.0228 (3) | |
C2 | 0.71562 (18) | 0.06981 (12) | 0.32239 (8) | 0.0222 (3) | |
C3 | 0.68987 (18) | −0.04493 (12) | 0.35496 (8) | 0.0208 (3) | |
C4 | 0.71766 (17) | −0.06357 (12) | 0.44682 (8) | 0.0192 (3) | |
C5 | 0.69070 (19) | −0.18034 (12) | 0.48476 (8) | 0.0228 (3) | |
C6 | 0.7177 (2) | −0.18951 (12) | 0.57287 (9) | 0.0259 (3) | |
C7 | 0.7708 (2) | −0.08462 (12) | 0.62532 (8) | 0.0232 (3) | |
C8 | 0.79680 (18) | 0.03144 (12) | 0.58907 (8) | 0.0203 (3) | |
C9 | 0.77033 (17) | 0.04058 (12) | 0.49904 (8) | 0.0189 (3) | |
C10 | 0.68711 (19) | 0.09120 (12) | 0.22717 (8) | 0.0243 (3) | |
C11 | 0.4574 (2) | 0.06738 (14) | 0.09645 (8) | 0.0342 (4) | |
C12 | 0.2371 (2) | 0.06161 (13) | 0.07099 (10) | 0.0354 (3) | |
C13 | 0.8508 (2) | 0.13608 (13) | 0.72459 (8) | 0.0291 (3) | |
H1 | 0.6533 | −0.1138 | 0.3172 | 0.025* | |
H2 | 0.6548 | −0.2522 | 0.4498 | 0.028* | |
H3 | 0.6992 | −0.2682 | 0.5988 | 0.032* | |
H4 | 0.7901 | −0.0931 | 0.6862 | 0.028* | |
H5 | 0.5166 | −0.0006 | 0.0712 | 0.041* | |
H6 | 0.5051 | 0.1446 | 0.0778 | 0.041* | |
H7 | 0.1804 | 0.1373 | 0.0874 | 0.041* | |
H8 | 0.2031 | 0.0512 | 0.0104 | 0.041* | |
H9 | 0.1879 | −0.0075 | 0.0990 | 0.041* | |
H10 | 0.7377 | 0.0924 | 0.7363 | 0.035* | |
H11 | 0.9674 | 0.0940 | 0.7516 | 0.036* | |
H12 | 0.8506 | 0.2194 | 0.7462 | 0.035* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0260 (5) | 0.0212 (5) | 0.0191 (5) | −0.0012 (3) | 0.0025 (3) | 0.0015 (3) |
O2 | 0.0459 (6) | 0.0250 (5) | 0.0294 (5) | −0.0020 (4) | 0.0024 (4) | 0.0076 (3) |
O3 | 0.0316 (6) | 0.0633 (7) | 0.0255 (5) | −0.0036 (5) | 0.0069 (4) | 0.0133 (4) |
O4 | 0.0259 (5) | 0.0356 (5) | 0.0147 (5) | 0.0013 (3) | 0.0012 (3) | 0.0014 (3) |
O5 | 0.0390 (6) | 0.0245 (5) | 0.0179 (5) | −0.0047 (3) | 0.0050 (4) | −0.0035 (3) |
C1 | 0.0212 (6) | 0.0261 (6) | 0.0203 (6) | 0.0026 (4) | 0.0013 (5) | 0.0044 (4) |
C2 | 0.0179 (6) | 0.0293 (7) | 0.0187 (6) | 0.0019 (4) | 0.0015 (4) | 0.0021 (4) |
C3 | 0.0162 (5) | 0.0275 (6) | 0.0184 (6) | −0.0009 (4) | 0.0018 (4) | −0.0012 (4) |
C4 | 0.0147 (5) | 0.0241 (6) | 0.0187 (6) | 0.0006 (4) | 0.0024 (4) | −0.0001 (4) |
C5 | 0.0235 (6) | 0.0221 (6) | 0.0230 (6) | −0.0026 (4) | 0.0048 (5) | −0.0014 (4) |
C6 | 0.0296 (7) | 0.0231 (6) | 0.0259 (7) | −0.0024 (5) | 0.0070 (5) | 0.0044 (5) |
C7 | 0.0247 (6) | 0.0280 (7) | 0.0170 (5) | 0.0002 (5) | 0.0037 (4) | 0.0015 (4) |
C8 | 0.0176 (5) | 0.0239 (6) | 0.0193 (6) | 0.0002 (4) | 0.0029 (4) | −0.0029 (4) |
C9 | 0.0153 (5) | 0.0213 (6) | 0.0201 (6) | 0.0009 (4) | 0.0032 (4) | 0.0024 (4) |
C10 | 0.0254 (6) | 0.0275 (6) | 0.0202 (6) | 0.0043 (5) | 0.0044 (5) | 0.0049 (4) |
C11 | 0.0392 (8) | 0.0481 (8) | 0.0138 (7) | 0.0086 (6) | 0.0008 (5) | 0.0022 (5) |
C12 | 0.0409 (8) | 0.0332 (7) | 0.0272 (7) | −0.0032 (5) | −0.0072 (6) | 0.0043 (5) |
C13 | 0.0353 (7) | 0.0349 (7) | 0.0175 (7) | −0.0042 (5) | 0.0059 (5) | −0.0052 (5) |
Geometric parameters (Å, º) top
O1—C1 | 1.3799 (15) | C7—C8 | 1.3859 (18) |
O1—C9 | 1.3729 (15) | C8—C9 | 1.4035 (17) |
O2—C1 | 1.2023 (16) | C11—C12 | 1.494 (2) |
O3—C10 | 1.2070 (17) | C3—H1 | 0.950 |
O4—C10 | 1.3260 (14) | C5—H2 | 0.950 |
O4—C11 | 1.4640 (14) | C6—H3 | 0.950 |
O5—C8 | 1.3593 (15) | C7—H4 | 0.950 |
O5—C13 | 1.4325 (16) | C11—H5 | 0.950 |
C1—C2 | 1.4612 (17) | C11—H6 | 0.950 |
C2—C3 | 1.3486 (18) | C12—H7 | 0.950 |
C2—C10 | 1.4980 (17) | C12—H8 | 0.950 |
C3—C4 | 1.4420 (17) | C12—H9 | 0.950 |
C4—C5 | 1.4058 (18) | C13—H10 | 0.950 |
C4—C9 | 1.3904 (17) | C13—H11 | 0.950 |
C5—C6 | 1.3734 (18) | C13—H12 | 0.950 |
C6—C7 | 1.3992 (18) | | |
| | | |
C1—O1—C9 | 122.22 (9) | C2—C3—H1 | 119.8 |
C10—O4—C11 | 116.83 (10) | C4—C3—H1 | 119.9 |
C8—O5—C13 | 117.06 (10) | C4—C5—H2 | 120.3 |
O1—C1—O2 | 117.41 (11) | C6—C5—H2 | 120.3 |
O1—C1—C2 | 116.32 (10) | C5—C6—H3 | 119.6 |
O2—C1—C2 | 126.25 (11) | C7—C6—H3 | 119.3 |
C1—C2—C3 | 121.74 (11) | C6—C7—H4 | 119.8 |
C1—C2—C10 | 117.11 (11) | C8—C7—H4 | 119.8 |
C3—C2—C10 | 121.14 (11) | O4—C11—H5 | 110.1 |
C2—C3—C4 | 120.31 (11) | O4—C11—H6 | 109.7 |
C3—C4—C5 | 123.07 (11) | C12—C11—H5 | 110.0 |
C3—C4—C9 | 117.42 (11) | C12—C11—H6 | 109.8 |
C5—C4—C9 | 119.50 (11) | H5—C11—H6 | 109.5 |
C4—C5—C6 | 119.32 (11) | C11—C12—H7 | 109.6 |
C5—C6—C7 | 121.11 (12) | C11—C12—H8 | 109.4 |
C6—C7—C8 | 120.40 (11) | C11—C12—H9 | 109.4 |
O5—C8—C7 | 125.49 (11) | H7—C12—H8 | 109.5 |
O5—C8—C9 | 116.06 (11) | H7—C12—H9 | 109.5 |
C7—C8—C9 | 118.45 (11) | H8—C12—H9 | 109.5 |
O1—C9—C4 | 121.97 (11) | O5—C13—H10 | 109.4 |
O1—C9—C8 | 116.80 (10) | O5—C13—H11 | 109.4 |
C4—C9—C8 | 121.22 (11) | O5—C13—H12 | 109.5 |
O3—C10—O4 | 125.57 (11) | H10—C13—H11 | 109.5 |
O3—C10—C2 | 124.21 (11) | H10—C13—H12 | 109.5 |
O4—C10—C2 | 110.22 (10) | H11—C13—H12 | 109.5 |
O4—C11—C12 | 107.65 (11) | | |
| | | |
C1—O1—C9—C4 | 1.33 (17) | C10—C2—C3—C4 | −179.88 (11) |
C1—O1—C9—C8 | −178.34 (11) | C2—C3—C4—C5 | 179.18 (12) |
C9—O1—C1—O2 | 177.13 (11) | C2—C3—C4—C9 | 0.28 (17) |
C9—O1—C1—C2 | −1.14 (16) | C3—C4—C5—C6 | −179.11 (12) |
C10—O4—C11—C12 | −165.03 (11) | C3—C4—C9—O1 | −0.85 (17) |
C11—O4—C10—O3 | 3.96 (19) | C3—C4—C9—C8 | 178.81 (11) |
C11—O4—C10—C2 | −176.31 (10) | C5—C4—C9—O1 | −179.78 (11) |
C13—O5—C8—C7 | −6.79 (18) | C5—C4—C9—C8 | −0.12 (18) |
C13—O5—C8—C9 | 172.90 (11) | C9—C4—C5—C6 | −0.24 (18) |
O1—C1—C2—C3 | 0.58 (17) | C4—C5—C6—C7 | 0.2 (2) |
O1—C1—C2—C10 | −179.70 (10) | C5—C6—C7—C8 | 0.2 (2) |
O2—C1—C2—C3 | −177.53 (13) | C6—C7—C8—O5 | 179.10 (12) |
O2—C1—C2—C10 | 2.20 (19) | C6—C7—C8—C9 | −0.57 (19) |
C1—C2—C3—C4 | −0.17 (18) | O5—C8—C9—O1 | 0.50 (16) |
C1—C2—C10—O3 | 58.38 (18) | O5—C8—C9—C4 | −179.18 (11) |
C1—C2—C10—O4 | −121.35 (12) | C7—C8—C9—O1 | −179.80 (11) |
C3—C2—C10—O3 | −121.89 (15) | C7—C8—C9—C4 | 0.52 (18) |
C3—C2—C10—O4 | 58.38 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H1···O3i | 0.95 | 2.72 | 3.5090 (17) | 141 |
C5—H2···O3i | 0.95 | 2.57 | 3.4022 (16) | 146 |
C12—H7···O5ii | 0.95 | 2.68 | 3.3729 (17) | 131 |
C13—H10···O4iii | 0.95 | 2.72 | 3.6357 (17) | 163 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1, −y, −z+1. |