Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059272/hg2332sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059272/hg2332Isup2.hkl |
CCDC reference: 616612
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.095
- wR factor = 0.295
- Data-to-parameter ratio = 10.8
checkCIF/PLATON results
No syntax errors found
Alert level B DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 1.071 Test value = 0.800 PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 1.07 e/A
Alert level C DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.295 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT084_ALERT_2_C High R2 Value .................................. 0.29 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.19 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.18 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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
For related literature, see: Allen et al. (1987); Brühlmann et al. (2001); García-Báez et al. (2002); Rollinger et al. (2004); Sharma et al. (2005); Shen & Zeng (2006); Zhang et al. (2006).
The reaction mixture containing 2,3,4-triacetoxy benzene (2.52 g, 10 mmol), acetoacetic ester (1.3 ml, 10 mmol) and phosphoric acid (5.3 ml) was stirred at 363–373 K for 12 h, and then poured into the water. The solid obtained was filtered off, washed with water and dried at room temperature. Colourless crystals of (I) suitable for X-ray structure analysis were obtained by slow evaporation of a ethanol solution with the crude product over three days. (M·P.555–557 K).
All H atoms were positioned geometrically and refined as riding on their parent atoms, with C—H = 0.96 Å (methyl), O—H = 0.82 Å (hydroxy) and Uiso(H)= 1.5Ueq(C,O), and C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for all other H atoms. The residual peaks (Δρmax = 1.07 e Å-3) and R (wR(F2) = 0.295) values are high because of poor crystal quality.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
C10H8O4 | Z = 2 |
Mr = 192.16 | F(000) = 200 |
Triclinic, P1 | Dx = 1.576 Mg m−3 |
Hall symbol: -P 1 | Melting point: 555 K |
a = 6.839 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.143 (3) Å | Cell parameters from 520 reflections |
c = 9.549 (3) Å | θ = 2.3–26.9° |
α = 68.233 (3)° | µ = 0.12 mm−1 |
β = 85.262 (3)° | T = 298 K |
γ = 69.443 (3)° | Prism, colourless |
V = 405.0 (2) Å3 | 0.56 × 0.15 × 0.13 mm |
Bruker SMART CCD area-detector diffractometer | 1397 independent reflections |
Radiation source: fine-focus sealed tube | 807 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→8 |
Tmin = 0.934, Tmax = 0.984 | k = −8→8 |
2098 measured reflections | l = −11→9 |
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)] = 0.095 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.295 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.1927P)2] where P = (Fo2 + 2Fc2)/3 |
1397 reflections | (Δ/σ)max < 0.001 |
129 parameters | Δρmax = 1.07 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
C10H8O4 | γ = 69.443 (3)° |
Mr = 192.16 | V = 405.0 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.839 (2) Å | Mo Kα radiation |
b = 7.143 (3) Å | µ = 0.12 mm−1 |
c = 9.549 (3) Å | T = 298 K |
α = 68.233 (3)° | 0.56 × 0.15 × 0.13 mm |
β = 85.262 (3)° |
Bruker SMART CCD area-detector diffractometer | 1397 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 807 reflections with I > 2σ(I) |
Tmin = 0.934, Tmax = 0.984 | Rint = 0.029 |
2098 measured reflections |
R[F2 > 2σ(F2)] = 0.095 | 0 restraints |
wR(F2) = 0.295 | H-atom parameters constrained |
S = 1.04 | Δρmax = 1.07 e Å−3 |
1397 reflections | Δρmin = −0.49 e Å−3 |
129 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 | 0.3392 (5) | 0.2706 (4) | 0.3419 (3) | 0.0317 (9) | |
O2 | 0.3742 (5) | 0.3077 (5) | 0.1047 (3) | 0.0387 (10) | |
O3 | 0.2139 (6) | 0.5590 (5) | 0.8112 (3) | 0.0457 (11) | |
H3 | 0.2451 | 0.4563 | 0.8916 | 0.069* | |
O4 | 0.3620 (5) | 0.1277 (5) | 0.8662 (3) | 0.0381 (10) | |
H4 | 0.4299 | 0.0067 | 0.8680 | 0.057* | |
C1 | 0.3200 (7) | 0.4023 (7) | 0.1939 (4) | 0.0293 (11) | |
C2 | 0.2386 (7) | 0.6265 (7) | 0.1609 (5) | 0.0330 (12) | |
H2 | 0.2153 | 0.7185 | 0.0602 | 0.040* | |
C3 | 0.1929 (7) | 0.7131 (7) | 0.2691 (5) | 0.0257 (11) | |
C4 | 0.2277 (6) | 0.5693 (6) | 0.4254 (4) | 0.0238 (11) | |
C5 | 0.1990 (7) | 0.6340 (6) | 0.5502 (4) | 0.0245 (11) | |
H5 | 0.1499 | 0.7798 | 0.5341 | 0.029* | |
C6 | 0.2419 (7) | 0.4867 (7) | 0.6950 (4) | 0.0283 (11) | |
C7 | 0.3178 (7) | 0.2672 (7) | 0.7203 (4) | 0.0261 (11) | |
C8 | 0.3444 (7) | 0.1995 (7) | 0.6007 (4) | 0.0267 (11) | |
H8 | 0.3898 | 0.0538 | 0.6168 | 0.032* | |
C9 | 0.3021 (6) | 0.3523 (6) | 0.4558 (4) | 0.0230 (11) | |
C10 | 0.1105 (8) | 0.9506 (7) | 0.2279 (5) | 0.0376 (13) | |
H10A | 0.1870 | 0.9891 | 0.2861 | 0.056* | |
H10B | −0.0349 | 0.9960 | 0.2486 | 0.056* | |
H10C | 0.1263 | 1.0196 | 0.1223 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.048 (2) | 0.0257 (16) | 0.0158 (15) | −0.0051 (14) | 0.0024 (13) | −0.0091 (12) |
O2 | 0.058 (2) | 0.0340 (18) | 0.0220 (17) | −0.0101 (16) | 0.0045 (15) | −0.0136 (14) |
O3 | 0.075 (3) | 0.0332 (19) | 0.0191 (17) | −0.0023 (17) | −0.0025 (16) | −0.0135 (14) |
O4 | 0.055 (2) | 0.0313 (17) | 0.0167 (16) | −0.0054 (16) | 0.0010 (14) | −0.0057 (13) |
C1 | 0.039 (3) | 0.031 (2) | 0.014 (2) | −0.009 (2) | 0.0021 (18) | −0.0073 (18) |
C2 | 0.039 (3) | 0.031 (2) | 0.021 (2) | −0.008 (2) | −0.001 (2) | −0.0036 (19) |
C3 | 0.024 (2) | 0.024 (2) | 0.024 (2) | −0.0048 (18) | 0.0008 (17) | −0.0061 (17) |
C4 | 0.019 (2) | 0.030 (2) | 0.022 (2) | −0.0075 (18) | 0.0028 (17) | −0.0098 (19) |
C5 | 0.026 (3) | 0.018 (2) | 0.027 (2) | −0.0034 (17) | 0.0025 (18) | −0.0096 (18) |
C6 | 0.027 (3) | 0.034 (2) | 0.022 (2) | −0.005 (2) | 0.0029 (18) | −0.0140 (19) |
C7 | 0.027 (3) | 0.030 (2) | 0.016 (2) | −0.0054 (19) | 0.0024 (17) | −0.0073 (17) |
C8 | 0.031 (3) | 0.024 (2) | 0.022 (2) | −0.0058 (19) | 0.0035 (18) | −0.0086 (18) |
C9 | 0.024 (2) | 0.022 (2) | 0.021 (2) | −0.0031 (17) | 0.0014 (17) | −0.0102 (17) |
C10 | 0.045 (3) | 0.029 (3) | 0.030 (3) | −0.007 (2) | 0.006 (2) | −0.007 (2) |
O1—C1 | 1.363 (5) | C4—C9 | 1.372 (6) |
O1—C9 | 1.382 (5) | C4—C5 | 1.407 (5) |
O2—C1 | 1.233 (5) | C5—C6 | 1.369 (6) |
O3—C6 | 1.362 (5) | C5—H5 | 0.9300 |
O3—H3 | 0.8200 | C6—C7 | 1.398 (6) |
O4—C7 | 1.361 (5) | C7—C8 | 1.373 (6) |
O4—H4 | 0.8200 | C8—C9 | 1.384 (6) |
C1—C2 | 1.415 (6) | C8—H8 | 0.9300 |
C2—C3 | 1.354 (6) | C10—H10A | 0.9600 |
C2—H2 | 0.9300 | C10—H10B | 0.9600 |
C3—C4 | 1.446 (6) | C10—H10C | 0.9600 |
C3—C10 | 1.490 (6) | ||
C1—O1—C9 | 121.1 (3) | O3—C6—C5 | 118.7 (4) |
C6—O3—H3 | 109.5 | O3—C6—C7 | 121.6 (4) |
C7—O4—H4 | 109.5 | C5—C6—C7 | 119.8 (4) |
O2—C1—O1 | 114.5 (4) | O4—C7—C8 | 122.5 (4) |
O2—C1—C2 | 128.1 (4) | O4—C7—C6 | 117.3 (4) |
O1—C1—C2 | 117.4 (4) | C8—C7—C6 | 120.1 (4) |
C3—C2—C1 | 123.0 (4) | C7—C8—C9 | 118.7 (4) |
C3—C2—H2 | 118.5 | C7—C8—H8 | 120.7 |
C1—C2—H2 | 118.5 | C9—C8—H8 | 120.7 |
C2—C3—C4 | 118.3 (4) | C4—C9—O1 | 121.8 (4) |
C2—C3—C10 | 120.8 (4) | C4—C9—C8 | 123.2 (4) |
C4—C3—C10 | 120.9 (4) | O1—C9—C8 | 115.0 (3) |
C9—C4—C5 | 116.8 (4) | C3—C10—H10A | 109.5 |
C9—C4—C3 | 118.1 (4) | C3—C10—H10B | 109.5 |
C5—C4—C3 | 125.1 (4) | H10A—C10—H10B | 109.5 |
C6—C5—C4 | 121.3 (4) | C3—C10—H10C | 109.5 |
C6—C5—H5 | 119.3 | H10A—C10—H10C | 109.5 |
C4—C5—H5 | 119.3 | H10B—C10—H10C | 109.5 |
C9—O1—C1—O2 | 174.3 (4) | O3—C6—C7—O4 | 0.3 (7) |
C9—O1—C1—C2 | −6.9 (6) | C5—C6—C7—O4 | 178.7 (4) |
O2—C1—C2—C3 | −176.9 (5) | O3—C6—C7—C8 | −180.0 (4) |
O1—C1—C2—C3 | 4.4 (7) | C5—C6—C7—C8 | −1.6 (7) |
C1—C2—C3—C4 | −0.5 (7) | O4—C7—C8—C9 | −177.9 (4) |
C1—C2—C3—C10 | 179.1 (4) | C6—C7—C8—C9 | 2.4 (7) |
C2—C3—C4—C9 | −1.0 (6) | C5—C4—C9—O1 | −179.0 (4) |
C10—C3—C4—C9 | 179.4 (4) | C3—C4—C9—O1 | −1.5 (6) |
C2—C3—C4—C5 | 176.3 (4) | C5—C4—C9—C8 | 1.4 (6) |
C10—C3—C4—C5 | −3.2 (7) | C3—C4—C9—C8 | 179.0 (4) |
C9—C4—C5—C6 | −0.5 (6) | C1—O1—C9—C4 | 5.6 (6) |
C3—C4—C5—C6 | −177.9 (4) | C1—O1—C9—C8 | −174.8 (4) |
C4—C5—C6—O3 | 179.1 (4) | C7—C8—C9—C4 | −2.4 (7) |
C4—C5—C6—C7 | 0.6 (7) | C7—C8—C9—O1 | 178.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.82 | 2.30 | 2.737 (4) | 114 |
O3—H3···O2i | 0.82 | 2.02 | 2.770 (4) | 152 |
O4—H4···O2ii | 0.82 | 2.10 | 2.917 (4) | 173 |
C8—H8···O1ii | 0.93 | 2.32 | 3.160 (5) | 150 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H8O4 |
Mr | 192.16 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 6.839 (2), 7.143 (3), 9.549 (3) |
α, β, γ (°) | 68.233 (3), 85.262 (3), 69.443 (3) |
V (Å3) | 405.0 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.56 × 0.15 × 0.13 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.934, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2098, 1397, 807 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.095, 0.295, 1.04 |
No. of reflections | 1397 |
No. of parameters | 129 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.07, −0.49 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.82 | 2.30 | 2.737 (4) | 114.1 |
O3—H3···O2i | 0.82 | 2.02 | 2.770 (4) | 151.7 |
O4—H4···O2ii | 0.82 | 2.10 | 2.917 (4) | 172.9 |
C8—H8···O1ii | 0.93 | 2.32 | 3.160 (5) | 149.9 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z+1. |
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7-Hydroxycoumarin derivatives are known to have a broad range of biological activities, including inhibition of Acetylcholinesterase and Monoamine Oxidase (Rollinger et al.,2004; Brühlmann et al., 2001), antioxidants (Sharma et al., 2005). The crystal structures of some 7-hydroxycoumarin derivatives (Zhang et al., 2006; Shen et al., 2006) have been described. Here we report the molecular structure of 6,7-dihydroxy-4-methyl-2H-1-benzopyran-2-one, (I).
In the molecule of (I), one intramolecular O—H···O hydrogen bond defines an S(5) pattern (García-Báez et al., 2002) (Fig. 1, Table 1). The molecule is almost planar, the dihedral angle between the benzene and pyran rings is 3.13 (3) Å. The geometric parameters for (I) are normal (Allen et al., 1987).
The molecules of (I) are linked by one O—H···O and one C—H···O hydrogen bonds into a centrosymmetric dimer of R22(8)R22(16)[R22(16)] (García-Báez et al., 2002) ring centred at (1/2, 0, 1/2)(Fig. 2 and Table 1). Atoms O4 and C8 in the molecule at (x, y, z) act as a hydrogen-bond donor to atoms O2 and O1 in the molecule at (1 - x, -y,1 - z), respectively. These dimers are connected by a pair of O—H···O hydrogen bonds into a ribbon in the [0 0 1] direction (Fig. 2 and Table 1). Atoms O3 in the molecules at (x, y, z) and (1 - x, -y, 2 - z) act as a hydrogen-bond donors to atoms O2 in the molecules at (x, y, 1 + z) and (1 - x, -y,1 - z), respectively. These adjacent ribbons are linked by π···π interacions into three-dimensional structure [Cg1···Cg2i= 3.687 (3) Å, Cg1···Cg2ii= 3.753 (3) Å; symmetry codes: (i)-x,1 - y,1 - z; (ii)1 - x,1 - y.1 - z; where Cg1 is centroid of the ring O1/C1—C4/C9 and Cg2 is centroid of the ring C4—C9.]