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In the title compound, C13H12O5, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018940/ob2019sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018940/ob2019Isup2.hkl
Contains datablock I

CCDC reference: 610860

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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-2H-1-benzopyran-3-carboxylate top
Crystal data top
C13H12O5F(000) = 520.00
Mr = 248.23Dx = 1.454 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ynCell parameters from 14368 reflections
a = 6.8572 (14) Åθ = 4.2–68.2°
b = 10.644 (2) ŵ = 0.95 mm1
c = 15.780 (3) ÅT = 173 K
β = 100.153 (14)°Prism, colorless
V = 1133.6 (4) Å30.40 × 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-1Rint = 0.027
ω scansθmax = 68.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 88
Tmin = 0.608, Tmax = 0.788k = 1212
14613 measured reflectionsl = 1818
2061 independent reflections
Refinement top
Refinement on F2H-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 = 1.00Δρmax = 0.32 e Å3
2061 reflectionsΔρmin = 0.50 e Å3
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
xyzUiso*/Ueq
O10.79794 (13)0.15692 (8)0.46548 (6)0.0223 (2)
O20.79140 (16)0.28452 (9)0.35466 (6)0.0340 (2)
O30.81319 (14)0.13218 (12)0.19016 (6)0.0399 (3)
O40.50483 (12)0.05925 (9)0.19045 (5)0.0257 (2)
O50.84569 (14)0.13967 (9)0.63348 (6)0.0271 (2)
C10.77138 (18)0.17849 (12)0.37797 (8)0.0228 (3)
C20.71562 (18)0.06981 (12)0.32239 (8)0.0222 (3)
C30.68987 (18)0.04493 (12)0.35496 (8)0.0208 (3)
C40.71766 (17)0.06357 (12)0.44682 (8)0.0192 (3)
C50.69070 (19)0.18034 (12)0.48476 (8)0.0228 (3)
C60.7177 (2)0.18951 (12)0.57287 (9)0.0259 (3)
C70.7708 (2)0.08462 (12)0.62532 (8)0.0232 (3)
C80.79680 (18)0.03144 (12)0.58907 (8)0.0203 (3)
C90.77033 (17)0.04058 (12)0.49904 (8)0.0189 (3)
C100.68711 (19)0.09120 (12)0.22717 (8)0.0243 (3)
C110.4574 (2)0.06738 (14)0.09645 (8)0.0342 (4)
C120.2371 (2)0.06161 (13)0.07099 (10)0.0354 (3)
C130.8508 (2)0.13608 (13)0.72459 (8)0.0291 (3)
H10.65330.11380.31720.025*
H20.65480.25220.44980.028*
H30.69920.26820.59880.032*
H40.79010.09310.68620.028*
H50.51660.00060.07120.041*
H60.50510.14460.07780.041*
H70.18040.13730.08740.041*
H80.20310.05120.01040.041*
H90.18790.00750.09900.041*
H100.73770.09240.73630.035*
H110.96740.09400.75160.036*
H120.85060.21940.74620.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0260 (5)0.0212 (5)0.0191 (5)0.0012 (3)0.0025 (3)0.0015 (3)
O20.0459 (6)0.0250 (5)0.0294 (5)0.0020 (4)0.0024 (4)0.0076 (3)
O30.0316 (6)0.0633 (7)0.0255 (5)0.0036 (5)0.0069 (4)0.0133 (4)
O40.0259 (5)0.0356 (5)0.0147 (5)0.0013 (3)0.0012 (3)0.0014 (3)
O50.0390 (6)0.0245 (5)0.0179 (5)0.0047 (3)0.0050 (4)0.0035 (3)
C10.0212 (6)0.0261 (6)0.0203 (6)0.0026 (4)0.0013 (5)0.0044 (4)
C20.0179 (6)0.0293 (7)0.0187 (6)0.0019 (4)0.0015 (4)0.0021 (4)
C30.0162 (5)0.0275 (6)0.0184 (6)0.0009 (4)0.0018 (4)0.0012 (4)
C40.0147 (5)0.0241 (6)0.0187 (6)0.0006 (4)0.0024 (4)0.0001 (4)
C50.0235 (6)0.0221 (6)0.0230 (6)0.0026 (4)0.0048 (5)0.0014 (4)
C60.0296 (7)0.0231 (6)0.0259 (7)0.0024 (5)0.0070 (5)0.0044 (5)
C70.0247 (6)0.0280 (7)0.0170 (5)0.0002 (5)0.0037 (4)0.0015 (4)
C80.0176 (5)0.0239 (6)0.0193 (6)0.0002 (4)0.0029 (4)0.0029 (4)
C90.0153 (5)0.0213 (6)0.0201 (6)0.0009 (4)0.0032 (4)0.0024 (4)
C100.0254 (6)0.0275 (6)0.0202 (6)0.0043 (5)0.0044 (5)0.0049 (4)
C110.0392 (8)0.0481 (8)0.0138 (7)0.0086 (6)0.0008 (5)0.0022 (5)
C120.0409 (8)0.0332 (7)0.0272 (7)0.0032 (5)0.0072 (6)0.0043 (5)
C130.0353 (7)0.0349 (7)0.0175 (7)0.0042 (5)0.0059 (5)0.0052 (5)
Geometric parameters (Å, º) top
O1—C11.3799 (15)C7—C81.3859 (18)
O1—C91.3729 (15)C8—C91.4035 (17)
O2—C11.2023 (16)C11—C121.494 (2)
O3—C101.2070 (17)C3—H10.950
O4—C101.3260 (14)C5—H20.950
O4—C111.4640 (14)C6—H30.950
O5—C81.3593 (15)C7—H40.950
O5—C131.4325 (16)C11—H50.950
C1—C21.4612 (17)C11—H60.950
C2—C31.3486 (18)C12—H70.950
C2—C101.4980 (17)C12—H80.950
C3—C41.4420 (17)C12—H90.950
C4—C51.4058 (18)C13—H100.950
C4—C91.3904 (17)C13—H110.950
C5—C61.3734 (18)C13—H120.950
C6—C71.3992 (18)
C1—O1—C9122.22 (9)C2—C3—H1119.8
C10—O4—C11116.83 (10)C4—C3—H1119.9
C8—O5—C13117.06 (10)C4—C5—H2120.3
O1—C1—O2117.41 (11)C6—C5—H2120.3
O1—C1—C2116.32 (10)C5—C6—H3119.6
O2—C1—C2126.25 (11)C7—C6—H3119.3
C1—C2—C3121.74 (11)C6—C7—H4119.8
C1—C2—C10117.11 (11)C8—C7—H4119.8
C3—C2—C10121.14 (11)O4—C11—H5110.1
C2—C3—C4120.31 (11)O4—C11—H6109.7
C3—C4—C5123.07 (11)C12—C11—H5110.0
C3—C4—C9117.42 (11)C12—C11—H6109.8
C5—C4—C9119.50 (11)H5—C11—H6109.5
C4—C5—C6119.32 (11)C11—C12—H7109.6
C5—C6—C7121.11 (12)C11—C12—H8109.4
C6—C7—C8120.40 (11)C11—C12—H9109.4
O5—C8—C7125.49 (11)H7—C12—H8109.5
O5—C8—C9116.06 (11)H7—C12—H9109.5
C7—C8—C9118.45 (11)H8—C12—H9109.5
O1—C9—C4121.97 (11)O5—C13—H10109.4
O1—C9—C8116.80 (10)O5—C13—H11109.4
C4—C9—C8121.22 (11)O5—C13—H12109.5
O3—C10—O4125.57 (11)H10—C13—H11109.5
O3—C10—C2124.21 (11)H10—C13—H12109.5
O4—C10—C2110.22 (10)H11—C13—H12109.5
O4—C11—C12107.65 (11)
C1—O1—C9—C41.33 (17)C10—C2—C3—C4179.88 (11)
C1—O1—C9—C8178.34 (11)C2—C3—C4—C5179.18 (12)
C9—O1—C1—O2177.13 (11)C2—C3—C4—C90.28 (17)
C9—O1—C1—C21.14 (16)C3—C4—C5—C6179.11 (12)
C10—O4—C11—C12165.03 (11)C3—C4—C9—O10.85 (17)
C11—O4—C10—O33.96 (19)C3—C4—C9—C8178.81 (11)
C11—O4—C10—C2176.31 (10)C5—C4—C9—O1179.78 (11)
C13—O5—C8—C76.79 (18)C5—C4—C9—C80.12 (18)
C13—O5—C8—C9172.90 (11)C9—C4—C5—C60.24 (18)
O1—C1—C2—C30.58 (17)C4—C5—C6—C70.2 (2)
O1—C1—C2—C10179.70 (10)C5—C6—C7—C80.2 (2)
O2—C1—C2—C3177.53 (13)C6—C7—C8—O5179.10 (12)
O2—C1—C2—C102.20 (19)C6—C7—C8—C90.57 (19)
C1—C2—C3—C40.17 (18)O5—C8—C9—O10.50 (16)
C1—C2—C10—O358.38 (18)O5—C8—C9—C4179.18 (11)
C1—C2—C10—O4121.35 (12)C7—C8—C9—O1179.80 (11)
C3—C2—C10—O3121.89 (15)C7—C8—C9—C40.52 (18)
C3—C2—C10—O458.38 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H1···O3i0.952.723.5090 (17)141
C5—H2···O3i0.952.573.4022 (16)146
C12—H7···O5ii0.952.683.3729 (17)131
C13—H10···O4iii0.952.723.6357 (17)163
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x1/2, y+1/2, z1/2; (iii) x+1, y, z+1.
 

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