Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032710/ci2411sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032710/ci2411Isup2.hkl |
CCDC reference: 657696
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.052
- wR factor = 0.135
- Data-to-parameter ratio = 20.1
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.794 1.000 Tmin(prime) and Tmax expected: 0.946 0.979 RR(prime) = 0.821 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.37 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the synthesis of the title compound, see: Furniss et al. (1989). For related structures, see: Toffoli et al. (1985); Bruno et al. (2001); Baumer et al. (2003, 2004); Zhong et al. (2006). For background, see: Pawar & Mulwad (2004); Lin et al. (2006); Urano et al. (1995); Zhang et al. (2003); Aggarwal et al. (1996).
The title compound was synthesized according to the method reported in the literature (Furniss et al., 1989). The compound was recrystallized from acetone-toluene (2:1 v/v) (m.p. 457 K).
The water H atoms were located in a difference Fourier map and refined with O—H distance restraints of 0.85 (1) Å, and with Uiso(H) values of 1.5Ueq(O). The remaining H atoms were included in calculated positions (O—H = 0.84 Å and C—H = 0.95 or 0.98 Å) and refined in riding model approximation, with Uiso(H) = 1.17–1.48Ueq(C).
Compounds incorporating benzopyrone structural units posses a wide range of biological activities. A coumarin nucleus is the basis of various compounds possessing anticoagulant and anti-inflammatory activities. 2H-2-Chromenone (coumarin) derivatives are widely used for production of highly effective fluorescent dyes for synthetic fibres and daylight fluorescent pigments. These derivatives also play a vital role in electrophotographic and electroluminiscent devices. Synthesis and investigation of new substituted 2H-2-chromenone derivatives make possible new ways for scientific and technical usage. The present day demand is for large and high quality ferroelectric, piezoelectric single crystals with minimum defects and inhomogenities. The important goal of crystal growth is the improvement of microscopic and macroscopic homogeneity, which is a necessity for any application. In addition, coumarin derivatives are known as bioactive compounds with weakly toxic, anticarcinogenic, anticoagulant and antibiotic activities. In continuation of our work on crystal structures of organic compounds and in view of the importance of the title compound, we report here its crystal structure.
The non-H atoms of the coumarin derivative are coplanar (Fig. 1), with a maximum deviation of 0.037 (1) Å for atom C4. The hydroxyl group is coplanar with the coumarin ring system. In the crystal structure, the molecules are linked into a two-dimensional network parallel to the (1 0 1) plane by O—H···O hydrogen bonds involving the water molecules (Fig. 2). In addition π-π stacking interaction is observed between the coumarin ring systems of the inversion related moleules stacked along the a axis, with a centroid-centroid separation of 3.536 (1) Å.
For the synthesis of the title compound, see: Furniss et al. (1989). For related structures, see: Toffoli et al. (1985); Bruno et al. (2001); Baumer et al. (2003, 2004); Zhong et al. (2006). For background, see: Pawar & Mulwad (2004); Lin et al. (2006); Urano et al. (1995); Zhang et al. (2003); Aggarwal et al. (1996).
Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C10H8O3·H2O | F(000) = 408 |
Mr = 194.18 | Dx = 1.446 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7134 reflections |
a = 6.9508 (5) Å | θ = 2.5–30.6° |
b = 11.3074 (8) Å | µ = 0.11 mm−1 |
c = 11.7833 (8) Å | T = 100 K |
β = 105.643 (1)° | Chunk, pale yellow |
V = 891.81 (11) Å3 | 0.48 × 0.30 × 0.19 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 2711 independent reflections |
Radiation source: fine-focus sealed tube | 2509 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 30.6°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −9→9 |
Tmin = 0.794, Tmax = 1.000 | k = −16→16 |
10240 measured reflections | l = −16→16 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.07P)2 + 0.3396P] where P = (Fo2 + 2Fc2)/3 |
2711 reflections | (Δ/σ)max = 0.001 |
135 parameters | Δρmax = 0.55 e Å−3 |
3 restraints | Δρmin = −0.23 e Å−3 |
C10H8O3·H2O | V = 891.81 (11) Å3 |
Mr = 194.18 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.9508 (5) Å | µ = 0.11 mm−1 |
b = 11.3074 (8) Å | T = 100 K |
c = 11.7833 (8) Å | 0.48 × 0.30 × 0.19 mm |
β = 105.643 (1)° |
Bruker APEXII CCD area-detector diffractometer | 2711 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 2509 reflections with I > 2σ(I) |
Tmin = 0.794, Tmax = 1.000 | Rint = 0.021 |
10240 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 3 restraints |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.55 e Å−3 |
2711 reflections | Δρmin = −0.23 e Å−3 |
135 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 | 0.02672 (15) | 0.15966 (7) | 0.42412 (8) | 0.0226 (2) | |
O2 | 0.46265 (13) | 0.69064 (7) | 0.65463 (7) | 0.0190 (2) | |
H2 | 0.4823 | 0.6504 | 0.7166 | 0.023* | |
O3 | 0.16176 (12) | 0.33058 (7) | 0.49034 (7) | 0.01523 (18) | |
O1W | 0.03518 (15) | −0.07764 (8) | 0.35966 (8) | 0.0228 (2) | |
H1W1 | 0.029 (3) | −0.0072 (13) | 0.3744 (17) | 0.034* | |
H1W2 | 0.006 (3) | −0.1104 (15) | 0.4179 (15) | 0.034* | |
C1 | 0.05814 (17) | 0.26209 (10) | 0.39892 (10) | 0.0161 (2) | |
C2 | −0.00631 (17) | 0.31431 (10) | 0.28374 (10) | 0.0166 (2) | |
H2A | −0.0804 | 0.2677 | 0.2198 | 0.020* | |
C3 | 0.03567 (16) | 0.42846 (10) | 0.26368 (9) | 0.0146 (2) | |
C4 | −0.03490 (18) | 0.48234 (11) | 0.14348 (10) | 0.0196 (2) | |
H4A | −0.1139 | 0.4242 | 0.0886 | 0.029* | |
H4B | 0.0807 | 0.5063 | 0.1163 | 0.029* | |
H4C | −0.1176 | 0.5517 | 0.1469 | 0.029* | |
C5 | 0.14888 (16) | 0.49870 (9) | 0.36148 (9) | 0.0132 (2) | |
C6 | 0.20288 (17) | 0.61797 (10) | 0.35288 (10) | 0.0156 (2) | |
H6A | 0.1667 | 0.6561 | 0.2783 | 0.019* | |
C7 | 0.30706 (17) | 0.68003 (10) | 0.45074 (10) | 0.0161 (2) | |
H7A | 0.3431 | 0.7601 | 0.4430 | 0.019* | |
C8 | 0.36036 (16) | 0.62531 (10) | 0.56205 (9) | 0.0143 (2) | |
C9 | 0.30837 (16) | 0.50774 (9) | 0.57400 (9) | 0.0139 (2) | |
H9A | 0.3421 | 0.4702 | 0.6489 | 0.017* | |
C10 | 0.20606 (16) | 0.44701 (9) | 0.47347 (9) | 0.0128 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0357 (5) | 0.0129 (4) | 0.0188 (4) | −0.0039 (3) | 0.0067 (4) | −0.0007 (3) |
O2 | 0.0258 (4) | 0.0143 (4) | 0.0146 (4) | −0.0039 (3) | 0.0013 (3) | −0.0018 (3) |
O3 | 0.0224 (4) | 0.0105 (3) | 0.0124 (4) | −0.0018 (3) | 0.0039 (3) | 0.0004 (3) |
O1W | 0.0376 (5) | 0.0148 (4) | 0.0164 (4) | 0.0019 (3) | 0.0079 (4) | 0.0006 (3) |
C1 | 0.0208 (5) | 0.0136 (5) | 0.0146 (5) | −0.0004 (4) | 0.0059 (4) | −0.0017 (4) |
C2 | 0.0208 (5) | 0.0163 (5) | 0.0124 (5) | −0.0011 (4) | 0.0039 (4) | −0.0021 (4) |
C3 | 0.0158 (5) | 0.0169 (5) | 0.0111 (4) | 0.0011 (4) | 0.0039 (3) | −0.0004 (4) |
C4 | 0.0233 (5) | 0.0217 (5) | 0.0121 (5) | −0.0002 (4) | 0.0020 (4) | 0.0023 (4) |
C5 | 0.0152 (5) | 0.0127 (4) | 0.0117 (4) | 0.0015 (3) | 0.0037 (3) | 0.0008 (3) |
C6 | 0.0179 (5) | 0.0142 (5) | 0.0144 (5) | 0.0010 (4) | 0.0039 (4) | 0.0032 (4) |
C7 | 0.0186 (5) | 0.0123 (5) | 0.0172 (5) | 0.0000 (4) | 0.0042 (4) | 0.0021 (4) |
C8 | 0.0152 (5) | 0.0132 (5) | 0.0145 (5) | 0.0005 (4) | 0.0039 (4) | −0.0009 (4) |
C9 | 0.0173 (5) | 0.0132 (4) | 0.0115 (4) | 0.0007 (4) | 0.0041 (4) | 0.0007 (3) |
C10 | 0.0158 (5) | 0.0100 (4) | 0.0129 (4) | 0.0009 (3) | 0.0043 (4) | 0.0010 (3) |
O1—C1 | 1.2298 (14) | C4—H4A | 0.98 |
O2—C8 | 1.3501 (13) | C4—H4B | 0.98 |
O2—H2 | 0.84 | C4—H4C | 0.98 |
O3—C1 | 1.3641 (13) | C5—C10 | 1.3993 (14) |
O3—C10 | 1.3786 (12) | C5—C6 | 1.4108 (15) |
O1W—H1W1 | 0.819 (14) | C6—C7 | 1.3770 (15) |
O1W—H1W2 | 0.851 (14) | C6—H6A | 0.95 |
C1—C2 | 1.4365 (15) | C7—C8 | 1.4065 (15) |
C2—C3 | 1.3579 (15) | C7—H7A | 0.95 |
C2—H2A | 0.95 | C8—C9 | 1.3947 (15) |
C3—C5 | 1.4454 (15) | C9—C10 | 1.3879 (14) |
C3—C4 | 1.4978 (15) | C9—H9A | 0.95 |
C8—O2—H2 | 109.5 | C10—C5—C6 | 116.98 (10) |
C1—O3—C10 | 121.28 (8) | C10—C5—C3 | 118.52 (9) |
H1W1—O1W—H1W2 | 102.4 (16) | C6—C5—C3 | 124.49 (10) |
O1—C1—O3 | 115.74 (10) | C7—C6—C5 | 121.13 (10) |
O1—C1—C2 | 125.80 (10) | C7—C6—H6A | 119.4 |
O3—C1—C2 | 118.46 (10) | C5—C6—H6A | 119.4 |
C3—C2—C1 | 121.89 (10) | C6—C7—C8 | 120.24 (10) |
C3—C2—H2A | 119.1 | C6—C7—H7A | 119.9 |
C1—C2—H2A | 119.1 | C8—C7—H7A | 119.9 |
C2—C3—C5 | 118.68 (10) | O2—C8—C9 | 122.30 (10) |
C2—C3—C4 | 121.35 (10) | O2—C8—C7 | 117.49 (10) |
C5—C3—C4 | 119.97 (10) | C9—C8—C7 | 120.21 (10) |
C3—C4—H4A | 109.5 | C10—C9—C8 | 118.20 (10) |
C3—C4—H4B | 109.5 | C10—C9—H9A | 120.9 |
H4A—C4—H4B | 109.5 | C8—C9—H9A | 120.9 |
C3—C4—H4C | 109.5 | O3—C10—C9 | 115.62 (9) |
H4A—C4—H4C | 109.5 | O3—C10—C5 | 121.15 (9) |
H4B—C4—H4C | 109.5 | C9—C10—C5 | 123.23 (10) |
C10—O3—C1—O1 | −179.87 (10) | C6—C7—C8—O2 | 179.91 (10) |
C10—O3—C1—C2 | −0.59 (15) | C6—C7—C8—C9 | 0.13 (17) |
O1—C1—C2—C3 | −179.79 (12) | O2—C8—C9—C10 | −178.93 (10) |
O3—C1—C2—C3 | 1.00 (17) | C7—C8—C9—C10 | 0.84 (16) |
C1—C2—C3—C5 | 0.13 (17) | C1—O3—C10—C9 | 178.66 (10) |
C1—C2—C3—C4 | −179.12 (11) | C1—O3—C10—C5 | −0.98 (15) |
C2—C3—C5—C10 | −1.65 (16) | C8—C9—C10—O3 | 178.91 (9) |
C4—C3—C5—C10 | 177.62 (10) | C8—C9—C10—C5 | −1.46 (17) |
C2—C3—C5—C6 | 179.90 (10) | C6—C5—C10—O3 | −179.33 (9) |
C4—C3—C5—C6 | −0.84 (17) | C3—C5—C10—O3 | 2.09 (15) |
C10—C5—C6—C7 | −0.03 (16) | C6—C5—C10—C9 | 1.06 (16) |
C3—C5—C6—C7 | 178.45 (10) | C3—C5—C10—C9 | −177.51 (10) |
C5—C6—C7—C8 | −0.54 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W2···O1i | 0.85 (1) | 2.01 (2) | 2.8509 (13) | 168 (2) |
O1W—H1W1···O1 | 0.82 (1) | 1.98 (2) | 2.7936 (13) | 175 (2) |
O2—H2···O1Wii | 0.84 | 1.82 | 2.6583 (12) | 174 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H8O3·H2O |
Mr | 194.18 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 6.9508 (5), 11.3074 (8), 11.7833 (8) |
β (°) | 105.643 (1) |
V (Å3) | 891.81 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.48 × 0.30 × 0.19 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.794, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10240, 2711, 2509 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.716 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.135, 1.13 |
No. of reflections | 2711 |
No. of parameters | 135 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.55, −0.23 |
Computer programs: APEX2 (Bruker, 2006), APEX2, SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W2···O1i | 0.851 (14) | 2.014 (15) | 2.8509 (13) | 168 (2) |
O1W—H1W1···O1 | 0.819 (14) | 1.976 (15) | 2.7936 (13) | 175 (2) |
O2—H2···O1Wii | 0.84 | 1.82 | 2.6583 (12) | 174 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1/2, −y+1/2, z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
Compounds incorporating benzopyrone structural units posses a wide range of biological activities. A coumarin nucleus is the basis of various compounds possessing anticoagulant and anti-inflammatory activities. 2H-2-Chromenone (coumarin) derivatives are widely used for production of highly effective fluorescent dyes for synthetic fibres and daylight fluorescent pigments. These derivatives also play a vital role in electrophotographic and electroluminiscent devices. Synthesis and investigation of new substituted 2H-2-chromenone derivatives make possible new ways for scientific and technical usage. The present day demand is for large and high quality ferroelectric, piezoelectric single crystals with minimum defects and inhomogenities. The important goal of crystal growth is the improvement of microscopic and macroscopic homogeneity, which is a necessity for any application. In addition, coumarin derivatives are known as bioactive compounds with weakly toxic, anticarcinogenic, anticoagulant and antibiotic activities. In continuation of our work on crystal structures of organic compounds and in view of the importance of the title compound, we report here its crystal structure.
The non-H atoms of the coumarin derivative are coplanar (Fig. 1), with a maximum deviation of 0.037 (1) Å for atom C4. The hydroxyl group is coplanar with the coumarin ring system. In the crystal structure, the molecules are linked into a two-dimensional network parallel to the (1 0 1) plane by O—H···O hydrogen bonds involving the water molecules (Fig. 2). In addition π-π stacking interaction is observed between the coumarin ring systems of the inversion related moleules stacked along the a axis, with a centroid-centroid separation of 3.536 (1) Å.