organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 7| July 2013| Pages o1081-o1082

2-Oxo-2H-chromen-4-yl 4-methyl­benzoate

aLaboratoire d'Instrumentation Image et Spectroscopie, DFR–GEE, Institut National Polytechnique Félix Houphouët-Boigny, BP 1093 Yamoussoukro, Côte d'Ivoire, bLaboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université Félix Houphouët-Boigny de Cocody, 22 BP 582 Abidjan 22, Côte d'Ivoire, and cLaboratoire de Chimie Bio-organique et de Phytochimie, Université de Ouagadougou, 03 BP 7021 Ouagadougou 03, Burkina Faso
*Correspondence e-mail: abou_akoun@yahoo.fr

(Received 23 May 2013; accepted 5 June 2013; online 12 June 2013)

The asymmetric unit of the title compound, C17H12O4, consists of two independent mol­ecules. The chromen-2-one ring and the 4-methyl­benzoate side chain are inclined to one another at a dihedral angle of 64.79 (10)° in one mol­ecule and 88.3 (1)° in the other. In the crystal, mol­ecules form R22(8) centrosymmetric dimers via C—H⋯O hydrogen bonds. These dimers are stacked by C—H⋯O hydrogen bonds, resulting in R22(18) and R32(16) ring motifs. ππ stacking inter­actions between two parallel chromen-2-one rings, with centroid–centroid distances of 3.743 (1) and 3.771 (1) Å, are also present.

Related literature

For related structures and background to coumarin derivatives, see: Abou et al. (2011[Abou, A., Djandé, A., Sessouma, B., Saba, A. & Kakou-Yao, R. (2011). Acta Cryst. E67, o2269-o2270.], 2012a[Abou, A., Sessouma, B., Djandé, A., Saba, A. & Kakou-Yao, R. (2012a). Acta Cryst. E68, o537-o538.],b[Abou, A., Djandé, A., Danger, G., Saba, A. & Kakou-Yao, R. (2012b). Acta Cryst. E68, o3438-o3439.]). For the biological activity of coumarin derivatives, see: Basanagouda et al. (2009[Basanagouda, M., Kulkarni, M. V., Sharma, D., Gupta, V. K., Sandhyarani, P. & Rasal, V. P. (2009). J. Chem. Sci. 121, 485-495.]); Vukovic et al. (2010[Vukovic, N., Sukdolak, S., Solujic, S. & Niciforovic, N. (2010). Arch. Pharm. Res. 33, 5-15.]); Emmanuel-Giota et al. (2001[Emmanuel-Giota, A. A., Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E. & Nicolaides, D. N. (2001). J. Heterocycl. Chem. 38, 717-722.]). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For ππ stacking inter­actions, see: Janiak (2000[Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12O4

  • Mr = 280.27

  • Triclinic, [P \overline 1]

  • a = 9.2790 (5) Å

  • b = 10.7696 (5) Å

  • c = 14.5758 (9) Å

  • α = 95.274 (2)°

  • β = 97.875 (2)°

  • γ = 104.788 (5)°

  • V = 1382.75 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 298 K

  • 0.35 × 0.20 × 0.20 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 16045 measured reflections

  • 6907 independent reflections

  • 3981 reflections with I > 2σ(I)

  • Rint = 0.055

Refinement
  • R[F2 > 2σ(F2)] = 0.071

  • wR(F2) = 0.193

  • S = 1.02

  • 6907 reflections

  • 381 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C5A—H5A⋯O4B 0.93 2.55 3.389 (3) 151
C8A—H8A⋯O2Bi 0.93 2.52 3.453 (3) 177
C8B—H8B⋯O2Ai 0.93 2.50 3.425 (3) 176
C12A—H12A⋯O2Ai 0.93 2.59 3.498 (3) 167
Symmetry code: (i) -x, -y, -z.

Data collection: COLLECT (Hooft, 1998[Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallograhy, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97, publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

Coumarins and their derivatives constitute one of the major classes of naturally occurring compounds and interest in their chemistry continues unabated because of their usefulness as biologically active agents. They also form the core of several molecules of pharmaceutical importance. Coumarin and its derivatives have been reported to serve as anti-bacterial (Basanagouda et al., 2009), anti-oxidant (Vukovic et al., 2010) and anti-inflammatory agents (Emmanuel-Giota et al., 2001). In view of their importance and as a continuation of our work on the crystal structure analysis of coumarin derivatives (Abou et al., 2011; 2012a,b), the title ester, (I), C17H12O5 has been synthesized and its molecular and crystal structure is reported herein.

The two independent molecules in the asymmetric unit of the title compound and the atomic labeling scheme are shown in Fig. 1. In these structures, the bond lengths in both independent molecules are comparable to those observed in related structures (Abou et al., 2011; 2012a,b). Also, the ten-membered chromen-2-one ring systems (O1A/C1A-C9A, O1B/C1B-C9B) of both independent molecules are essentially planar [the maximum deviation from planarity being respectively 0.014 (3) Å for atoms C2A and C4A (molecule A), and -0.010 (2) Å for atom O1B (molecule B)]. In the asymmetric unit, the two chromen-2-one ring systems are parallel displaced, as evidenced by the dihedral angle of 1.25 (7)° between them. In addition, the planar 4-methylbenzoate moieties of the two independent molecules are tilted with respect to one another with a dihedral angle of 26.14 (12)° between them. Furthermore, the angles between the chromen-2-one ring planes and the 4-methylbenzoate side chains of the two independent molecules are inclined at dihedral angles of 64.79 (10)° for molecule A and 88.3 (1)° for molecule B.

In the crystal, we observe the formation of R22(8) centrosymmetric dimers (Bernstein et al., 1995) between A and B molecules via C8A—H8A···O2B and C8B—H8B···O2A hydrogen bonds while two adjacent B molecules form similar rings through C2B—H2B···O1B contacts. The dimers are linked to each other by C12A—H12A···O2Ai and C12Ai–H12i···O2A hydrogen bonds to form an R22(18) ring motif and C5A–H5A···O4B, C8B—H8B···O2Ai and C12A—H12A···O2Ai contacts [symmetry operation i: - x, - y, - z] result in an R32(16) ring motif (Table 1, Fig.2). The supramolecular aggregation is completed by the presence of π···π stacking interactions between two parallel chromen-2-one rings; in the latter, the centroid···centroid distances, Cg1···Cg6 (x - 1, y, z) = 3.771 (1), Cg2···Cg5 = 3.7433 (13) Å, where Cg1, Cg2, Cg5 and Cg6 are centroids of the O1A/C1A/C6A-C9A, C1A/C2A-C6A, O1B/C1B/C6B-C9B and C1B/C2B-C6B rings respectively, are both less than 3.8 Å, the maximum regarded as reasonable for π···π interactions (Janiak, 2000) (Fig. 3).

Related literature top

For related structures and background to coumarin derivatives, see: Abou et al. (2011, 2012a,b). For the biological activity of coumarin derivatives, see: Basanagouda et al. (2009); Vukovic et al. (2010); Emmanuel-Giota et al. (2001). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995). For ππ stacking interactions, see: Janiak (2000).

Experimental top

To a solution of p-toluoyl chloride (40 mmole) in dried tetrahydrofuran (150 ml), was added dried triethylamine (120 mmole) and 4-hydroxycoumarin (40 mmole) in small portions over 30 min.The mixture was then refluxed for 3 h and poured into 300 ml of chloroform. The solution was acidified with dilute hydrochloric acid until the pH was 2 - 3. The organic layer was extracted, washed with water, dried over MgSO4 and the solvent removed. The crude product was recrystallized from a chloroform-acetone (1/3, v/v) mixture. Colourless crystals of the title compound were obtained in a good yield: 76%; M.pt. 393 K.

Refinement top

H atoms were placed in calculated positions [C—H = 0.93 (aromatic) or 0.96 Å (methyl group)] and refined using a riding model approximation with Uiso(H) constrained to 1.2 (aromatic) or 1.5 (methyl) times Ueq of the respective parent atom.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic labeling scheme with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
[Figure 2] Fig. 2. Crystal packing, showing the R22(8) centrosymmetric dimers stacked by hydrogen bonds to form R22(18) and R32(16) ring motifs. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonds have been omitted for clarity.
[Figure 3] Fig. 3. A view of the crystal packing, showing π···π stacking interactions (dashed lines). The green dots are centroids of rings. H atoms have been omitted for clarity.
2-Oxo-2H-chromen-4-yl 4-methylbenzoate top
Crystal data top
C17H12O4Z = 4
Mr = 280.27F(000) = 584
Triclinic, P1Dx = 1.346 Mg m3
Hall symbol: -P 1Melting point: 393 K
a = 9.2790 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7696 (5) ÅCell parameters from 16045 reflections
c = 14.5758 (9) Åθ = 2.3–29.0°
α = 95.274 (2)°µ = 0.10 mm1
β = 97.875 (2)°T = 298 K
γ = 104.788 (5)°Prism, colourless
V = 1382.75 (13) Å30.35 × 0.20 × 0.20 mm
Data collection top
Nonius KappaCCD
diffractometer
3981 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 29.0°, θmin = 2.3°
ϕ and ω scansh = 012
16045 measured reflectionsk = 1413
6907 independent reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0648P)2 + 0.5338P]
where P = (Fo2 + 2Fc2)/3
6907 reflections(Δ/σ)max < 0.001
381 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.18 e Å3
96 constraints
Crystal data top
C17H12O4γ = 104.788 (5)°
Mr = 280.27V = 1382.75 (13) Å3
Triclinic, P1Z = 4
a = 9.2790 (5) ÅMo Kα radiation
b = 10.7696 (5) ŵ = 0.10 mm1
c = 14.5758 (9) ÅT = 298 K
α = 95.274 (2)°0.35 × 0.20 × 0.20 mm
β = 97.875 (2)°
Data collection top
Nonius KappaCCD
diffractometer
3981 reflections with I > 2σ(I)
16045 measured reflectionsRint = 0.055
6907 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0710 restraints
wR(F2) = 0.193H-atom parameters constrained
S = 1.02Δρmax = 0.21 e Å3
6907 reflectionsΔρmin = 0.18 e Å3
381 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O3A0.11504 (16)0.06541 (13)0.19401 (10)0.0531 (4)
O1A0.01309 (17)0.34133 (13)0.03537 (10)0.0563 (4)
O3B0.59037 (18)0.04620 (14)0.18431 (10)0.0586 (4)
O1B0.48955 (17)0.32568 (14)0.02929 (10)0.0571 (4)
C6A0.1773 (2)0.28926 (19)0.16105 (14)0.0465 (5)
C7A0.0784 (2)0.16012 (18)0.14343 (14)0.0470 (5)
O4A0.0360 (2)0.14818 (16)0.31869 (12)0.0733 (5)
O4B0.4891 (2)0.11458 (17)0.30383 (12)0.0769 (5)
C8A0.0434 (2)0.1250 (2)0.07677 (14)0.0529 (5)
H8A0.10430.04020.06750.063*
O2B0.28103 (19)0.18531 (17)0.04626 (11)0.0718 (5)
C11B0.5954 (2)0.06380 (19)0.31683 (14)0.0475 (5)
C1A0.1380 (2)0.37749 (19)0.10450 (14)0.0486 (5)
O2A0.1896 (2)0.19687 (17)0.04247 (11)0.0747 (5)
C6B0.6536 (2)0.26919 (19)0.15259 (14)0.0485 (5)
C12A0.1485 (2)0.1468 (2)0.27689 (16)0.0554 (5)
H12A0.15480.14670.21380.066*
C12B0.6854 (2)0.1337 (2)0.28147 (16)0.0569 (5)
H12B0.71910.11800.22530.068*
C11A0.1175 (2)0.04418 (19)0.32675 (14)0.0474 (5)
C8B0.4294 (2)0.1088 (2)0.06938 (15)0.0546 (5)
H8B0.36720.02450.05970.065*
C5B0.7849 (3)0.3096 (2)0.21943 (16)0.0602 (6)
H5B0.81220.25150.25720.072*
C10A0.0850 (2)0.0663 (2)0.28306 (15)0.0505 (5)
C7B0.5523 (2)0.14119 (19)0.13453 (14)0.0488 (5)
C10B0.5508 (2)0.0404 (2)0.27117 (15)0.0519 (5)
C9A0.0812 (3)0.2178 (2)0.01896 (15)0.0550 (5)
C14B0.6753 (3)0.2549 (2)0.41256 (17)0.0625 (6)
C5A0.3081 (2)0.3320 (2)0.22844 (16)0.0570 (5)
H5A0.33690.27490.26660.068*
C2B0.7047 (3)0.4859 (2)0.10754 (17)0.0621 (6)
H2B0.67760.54490.07060.075*
C14A0.1632 (3)0.2525 (2)0.41558 (18)0.0642 (6)
C2A0.2240 (3)0.5053 (2)0.11509 (17)0.0607 (6)
H2A0.19580.56340.07760.073*
C13A0.1701 (3)0.2502 (2)0.32218 (18)0.0647 (6)
H13A0.18970.31980.28830.078*
C13B0.7251 (3)0.2278 (2)0.33042 (18)0.0672 (6)
H13B0.78730.27380.30690.081*
C1B0.6160 (2)0.3591 (2)0.09711 (15)0.0504 (5)
C16A0.1124 (3)0.0446 (2)0.42087 (16)0.0614 (6)
H16A0.09370.02520.45500.074*
C16B0.5426 (3)0.0917 (2)0.39887 (16)0.0645 (6)
H16B0.47930.04670.42220.077*
C9B0.3917 (3)0.2034 (2)0.01344 (15)0.0553 (5)
C15B0.5834 (3)0.1862 (2)0.44628 (18)0.0704 (7)
H15B0.54820.20340.50180.084*
C15A0.1347 (3)0.1482 (2)0.46484 (17)0.0669 (6)
H15A0.13050.14750.52830.080*
C3A0.3513 (3)0.5444 (2)0.18176 (19)0.0688 (7)
H3A0.41000.62990.18940.083*
C3B0.8335 (3)0.5225 (2)0.17352 (19)0.0710 (7)
H3B0.89470.60710.18090.085*
C4A0.3943 (3)0.4586 (2)0.23823 (18)0.0676 (6)
H4A0.48160.48680.28280.081*
C4B0.8738 (3)0.4349 (3)0.22938 (18)0.0706 (7)
H4B0.96150.46130.27380.085*
C17A0.1883 (4)0.3653 (3)0.4641 (2)0.0970 (10)
H17A0.24890.40770.43110.145*
H17B0.09250.42560.46500.145*
H17C0.23940.33410.52700.145*
C17B0.7220 (4)0.3568 (3)0.4659 (2)0.0941 (10)
H17D0.79360.31510.52090.141*
H17E0.76740.40730.42700.141*
H17F0.63460.41240.48370.141*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O3A0.0750 (9)0.0470 (8)0.0501 (8)0.0318 (7)0.0174 (7)0.0181 (6)
O1A0.0718 (10)0.0490 (8)0.0528 (9)0.0237 (7)0.0061 (7)0.0169 (7)
O3B0.0833 (10)0.0533 (9)0.0554 (9)0.0381 (8)0.0204 (8)0.0221 (7)
O1B0.0677 (9)0.0519 (9)0.0574 (9)0.0229 (7)0.0080 (7)0.0205 (7)
C6A0.0551 (11)0.0456 (11)0.0471 (11)0.0241 (9)0.0141 (9)0.0115 (9)
C7A0.0635 (12)0.0413 (10)0.0463 (11)0.0256 (9)0.0162 (9)0.0140 (9)
O4A0.1083 (13)0.0706 (11)0.0678 (11)0.0547 (10)0.0364 (10)0.0261 (9)
O4B0.1064 (14)0.0820 (12)0.0737 (11)0.0626 (11)0.0372 (10)0.0318 (9)
C8A0.0674 (13)0.0441 (11)0.0502 (12)0.0188 (10)0.0094 (10)0.0115 (9)
O2B0.0790 (11)0.0765 (11)0.0596 (10)0.0251 (9)0.0017 (8)0.0161 (8)
C11B0.0487 (11)0.0442 (11)0.0519 (12)0.0155 (8)0.0060 (9)0.0138 (9)
C1A0.0587 (12)0.0449 (11)0.0498 (12)0.0225 (9)0.0149 (9)0.0119 (9)
O2A0.0893 (12)0.0706 (11)0.0604 (10)0.0251 (9)0.0104 (9)0.0129 (8)
C6B0.0564 (12)0.0506 (11)0.0477 (12)0.0250 (9)0.0162 (9)0.0125 (9)
C12A0.0650 (13)0.0490 (12)0.0562 (13)0.0203 (10)0.0103 (10)0.0140 (10)
C12B0.0660 (13)0.0522 (12)0.0602 (14)0.0251 (10)0.0145 (10)0.0158 (10)
C11A0.0491 (11)0.0452 (11)0.0508 (12)0.0149 (8)0.0086 (9)0.0148 (9)
C8B0.0677 (13)0.0468 (11)0.0533 (13)0.0199 (10)0.0119 (10)0.0123 (10)
C5B0.0610 (13)0.0673 (15)0.0591 (14)0.0270 (11)0.0110 (10)0.0140 (11)
C10A0.0589 (12)0.0484 (11)0.0517 (12)0.0217 (9)0.0149 (9)0.0152 (9)
C7B0.0637 (13)0.0470 (11)0.0472 (11)0.0276 (9)0.0174 (9)0.0162 (9)
C10B0.0575 (12)0.0504 (12)0.0546 (13)0.0233 (10)0.0106 (9)0.0143 (10)
C9A0.0690 (14)0.0524 (12)0.0471 (12)0.0231 (10)0.0072 (10)0.0090 (10)
C14B0.0656 (14)0.0467 (12)0.0716 (16)0.0135 (10)0.0054 (11)0.0204 (11)
C5A0.0583 (13)0.0593 (13)0.0599 (14)0.0260 (10)0.0098 (10)0.0126 (11)
C2B0.0731 (15)0.0505 (13)0.0728 (16)0.0234 (11)0.0255 (12)0.0200 (11)
C14A0.0637 (14)0.0551 (13)0.0766 (17)0.0160 (10)0.0061 (11)0.0320 (12)
C2A0.0721 (15)0.0469 (12)0.0719 (15)0.0225 (11)0.0234 (12)0.0182 (11)
C13A0.0791 (16)0.0478 (12)0.0753 (17)0.0274 (11)0.0139 (12)0.0184 (11)
C13B0.0781 (16)0.0569 (14)0.0772 (17)0.0353 (12)0.0106 (13)0.0181 (12)
C1B0.0556 (12)0.0502 (12)0.0532 (12)0.0227 (9)0.0155 (9)0.0131 (9)
C16A0.0754 (15)0.0605 (14)0.0558 (14)0.0235 (11)0.0196 (11)0.0188 (11)
C16B0.0726 (15)0.0713 (15)0.0614 (15)0.0323 (12)0.0185 (11)0.0223 (12)
C9B0.0672 (14)0.0572 (13)0.0475 (12)0.0255 (11)0.0108 (10)0.0114 (10)
C15B0.0786 (16)0.0749 (16)0.0636 (15)0.0232 (13)0.0127 (12)0.0314 (13)
C15A0.0760 (16)0.0719 (16)0.0582 (14)0.0212 (12)0.0132 (11)0.0303 (12)
C3A0.0692 (15)0.0485 (13)0.0898 (19)0.0136 (11)0.0226 (13)0.0077 (12)
C3B0.0689 (15)0.0584 (14)0.0841 (18)0.0114 (12)0.0204 (13)0.0054 (13)
C4A0.0573 (14)0.0634 (15)0.0784 (17)0.0145 (11)0.0062 (11)0.0032 (12)
C4B0.0609 (14)0.0757 (17)0.0711 (17)0.0152 (12)0.0066 (12)0.0042 (13)
C17A0.110 (2)0.0798 (19)0.114 (2)0.0353 (17)0.0117 (18)0.0591 (18)
C17B0.113 (2)0.0727 (18)0.100 (2)0.0330 (16)0.0055 (18)0.0416 (16)
Geometric parameters (Å, º) top
O3A—C10A1.364 (2)C5B—C4B1.374 (3)
O3A—C7A1.395 (2)C5B—H5B0.9300
O1A—C9A1.372 (3)C14B—C13B1.371 (3)
O1A—C1A1.374 (3)C14B—C15B1.374 (3)
O3B—C10B1.368 (2)C14B—C17B1.518 (3)
O3B—C7B1.396 (2)C5A—C4A1.377 (3)
O1B—C1B1.373 (3)C5A—H5A0.9300
O1B—C9B1.374 (3)C2B—C3B1.373 (3)
C6A—C1A1.397 (3)C2B—C1B1.384 (3)
C6A—C5A1.398 (3)C2B—H2B0.9300
C6A—C7A1.435 (3)C14A—C13A1.374 (3)
C7A—C8A1.333 (3)C14A—C15A1.379 (3)
O4A—C10A1.199 (2)C14A—C17A1.512 (3)
O4B—C10B1.196 (2)C2A—C3A1.369 (3)
C8A—C9A1.444 (3)C2A—H2A0.9300
C8A—H8A0.9300C13A—H13A0.9300
O2B—C9B1.213 (3)C13B—H13B0.9300
C11B—C12B1.377 (3)C16A—C15A1.382 (3)
C11B—C16B1.383 (3)C16A—H16A0.9300
C11B—C10B1.474 (3)C16B—C15B1.382 (3)
C1A—C2A1.387 (3)C16B—H16B0.9300
O2A—C9A1.210 (3)C15B—H15B0.9300
C6B—C5B1.396 (3)C15A—H15A0.9300
C6B—C1B1.398 (3)C3A—C4A1.389 (3)
C6B—C7B1.434 (3)C3A—H3A0.9300
C12A—C11A1.379 (3)C3B—C4B1.389 (4)
C12A—C13A1.389 (3)C3B—H3B0.9300
C12A—H12A0.9300C4A—H4A0.9300
C12B—C13B1.387 (3)C4B—H4B0.9300
C12B—H12B0.9300C17A—H17A0.9600
C11A—C16A1.380 (3)C17A—H17B0.9600
C11A—C10A1.478 (3)C17A—H17C0.9600
C8B—C7B1.328 (3)C17B—H17D0.9600
C8B—C9B1.443 (3)C17B—H17E0.9600
C8B—H8B0.9300C17B—H17F0.9600
C10A—O3A—C7A117.12 (15)C3B—C2B—H2B120.7
C9A—O1A—C1A122.10 (16)C1B—C2B—H2B120.7
C10B—O3B—C7B116.80 (15)C13A—C14A—C15A118.3 (2)
C1B—O1B—C9B122.14 (16)C13A—C14A—C17A121.2 (2)
C1A—C6A—C5A118.44 (19)C15A—C14A—C17A120.4 (2)
C1A—C6A—C7A116.09 (19)C3A—C2A—C1A118.7 (2)
C5A—C6A—C7A125.46 (19)C3A—C2A—H2A120.6
C8A—C7A—O3A118.30 (18)C1A—C2A—H2A120.6
C8A—C7A—C6A122.48 (18)C14A—C13A—C12A121.8 (2)
O3A—C7A—C6A119.12 (18)C14A—C13A—H13A119.1
C7A—C8A—C9A120.4 (2)C12A—C13A—H13A119.1
C7A—C8A—H8A119.8C14B—C13B—C12B121.8 (2)
C9A—C8A—H8A119.8C14B—C13B—H13B119.1
C12B—C11B—C16B119.31 (19)C12B—C13B—H13B119.1
C12B—C11B—C10B123.22 (19)O1B—C1B—C2B116.85 (19)
C16B—C11B—C10B117.47 (19)O1B—C1B—C6B121.46 (19)
O1A—C1A—C2A116.91 (19)C2B—C1B—C6B121.7 (2)
O1A—C1A—C6A121.55 (18)C11A—C16A—C15A120.5 (2)
C2A—C1A—C6A121.5 (2)C11A—C16A—H16A119.8
C5B—C6B—C1B118.4 (2)C15A—C16A—H16A119.8
C5B—C6B—C7B125.57 (19)C15B—C16B—C11B120.3 (2)
C1B—C6B—C7B116.06 (19)C15B—C16B—H16B119.9
C11A—C12A—C13A119.2 (2)C11B—C16B—H16B119.9
C11A—C12A—H12A120.4O2B—C9B—O1B116.8 (2)
C13A—C12A—H12A120.4O2B—C9B—C8B126.1 (2)
C11B—C12B—C13B119.3 (2)O1B—C9B—C8B117.19 (19)
C11B—C12B—H12B120.3C14B—C15B—C16B120.9 (2)
C13B—C12B—H12B120.3C14B—C15B—H15B119.5
C12A—C11A—C16A119.53 (19)C16B—C15B—H15B119.5
C12A—C11A—C10A122.71 (19)C14A—C15A—C16A120.6 (2)
C16A—C11A—C10A117.74 (19)C14A—C15A—H15A119.7
C7B—C8B—C9B120.5 (2)C16A—C15A—H15A119.7
C7B—C8B—H8B119.7C2A—C3A—C4A121.1 (2)
C9B—C8B—H8B119.7C2A—C3A—H3A119.5
C4B—C5B—C6B120.1 (2)C4A—C3A—H3A119.5
C4B—C5B—H5B120.0C2B—C3B—C4B120.9 (2)
C6B—C5B—H5B120.0C2B—C3B—H3B119.6
O4A—C10A—O3A122.06 (18)C4B—C3B—H3B119.5
O4A—C10A—C11A125.86 (19)C5A—C4A—C3A120.2 (2)
O3A—C10A—C11A112.07 (17)C5A—C4A—H4A119.9
C8B—C7B—O3B119.35 (19)C3A—C4A—H4A119.9
C8B—C7B—C6B122.58 (19)C5B—C4B—C3B120.4 (2)
O3B—C7B—C6B117.97 (18)C5B—C4B—H4B119.8
O4B—C10B—O3B121.76 (18)C3B—C4B—H4B119.8
O4B—C10B—C11B126.1 (2)C14A—C17A—H17A109.5
O3B—C10B—C11B112.09 (17)C14A—C17A—H17B109.5
O2A—C9A—O1A116.75 (19)H17A—C17A—H17B109.5
O2A—C9A—C8A125.9 (2)C14A—C17A—H17C109.5
O1A—C9A—C8A117.37 (19)H17A—C17A—H17C109.5
C13B—C14B—C15B118.3 (2)H17B—C17A—H17C109.5
C13B—C14B—C17B121.1 (2)C14B—C17B—H17D109.5
C15B—C14B—C17B120.6 (2)C14B—C17B—H17E109.5
C4A—C5A—C6A120.0 (2)H17D—C17B—H17E109.5
C4A—C5A—H5A120.0C14B—C17B—H17F109.5
C6A—C5A—H5A120.0H17D—C17B—H17F109.5
C3B—C2B—C1B118.6 (2)H17E—C17B—H17F109.5
C10A—O3A—C7A—C8A105.1 (2)C1A—O1A—C9A—C8A0.8 (3)
C10A—O3A—C7A—C6A78.5 (2)C7A—C8A—C9A—O2A179.0 (2)
C1A—C6A—C7A—C8A0.5 (3)C7A—C8A—C9A—O1A0.3 (3)
C5A—C6A—C7A—C8A178.7 (2)C1A—C6A—C5A—C4A0.4 (3)
C1A—C6A—C7A—O3A176.72 (16)C7A—C6A—C5A—C4A179.6 (2)
C5A—C6A—C7A—O3A2.5 (3)O1A—C1A—C2A—C3A178.52 (19)
O3A—C7A—C8A—C9A176.50 (17)C6A—C1A—C2A—C3A1.0 (3)
C6A—C7A—C8A—C9A0.2 (3)C15A—C14A—C13A—C12A0.3 (4)
C9A—O1A—C1A—C2A179.40 (18)C17A—C14A—C13A—C12A179.5 (2)
C9A—O1A—C1A—C6A1.1 (3)C11A—C12A—C13A—C14A0.8 (3)
C5A—C6A—C1A—O1A178.39 (18)C15B—C14B—C13B—C12B0.1 (4)
C7A—C6A—C1A—O1A0.9 (3)C17B—C14B—C13B—C12B179.0 (2)
C5A—C6A—C1A—C2A1.1 (3)C11B—C12B—C13B—C14B1.1 (4)
C7A—C6A—C1A—C2A179.61 (18)C9B—O1B—C1B—C2B178.96 (19)
C16B—C11B—C12B—C13B2.1 (3)C9B—O1B—C1B—C6B1.4 (3)
C10B—C11B—C12B—C13B178.3 (2)C3B—C2B—C1B—O1B178.88 (19)
C13A—C12A—C11A—C16A1.6 (3)C3B—C2B—C1B—C6B0.8 (3)
C13A—C12A—C11A—C10A176.7 (2)C5B—C6B—C1B—O1B179.20 (18)
C1B—C6B—C5B—C4B0.1 (3)C7B—C6B—C1B—O1B0.3 (3)
C7B—C6B—C5B—C4B179.3 (2)C5B—C6B—C1B—C2B0.5 (3)
C7A—O3A—C10A—O4A3.5 (3)C7B—C6B—C1B—C2B179.91 (19)
C7A—O3A—C10A—C11A175.57 (17)C12A—C11A—C16A—C15A1.4 (3)
C12A—C11A—C10A—O4A168.4 (2)C10A—C11A—C16A—C15A177.0 (2)
C16A—C11A—C10A—O4A9.9 (3)C12B—C11B—C16B—C15B1.9 (3)
C12A—C11A—C10A—O3A10.7 (3)C10B—C11B—C16B—C15B178.4 (2)
C16A—C11A—C10A—O3A171.03 (18)C1B—O1B—C9B—O2B177.83 (19)
C9B—C8B—C7B—O3B176.69 (18)C1B—O1B—C9B—C8B1.9 (3)
C9B—C8B—C7B—C6B0.4 (3)C7B—C8B—C9B—O2B178.3 (2)
C10B—O3B—C7B—C8B99.2 (2)C7B—C8B—C9B—O1B1.5 (3)
C10B—O3B—C7B—C6B84.4 (2)C13B—C14B—C15B—C16B0.2 (4)
C5B—C6B—C7B—C8B179.6 (2)C17B—C14B—C15B—C16B178.9 (2)
C1B—C6B—C7B—C8B0.2 (3)C11B—C16B—C15B—C14B0.8 (4)
C5B—C6B—C7B—O3B3.3 (3)C13A—C14A—C15A—C16A0.6 (4)
C1B—C6B—C7B—O3B176.12 (16)C17A—C14A—C15A—C16A179.7 (2)
C7B—O3B—C10B—O4B1.4 (3)C11A—C16A—C15A—C14A0.3 (4)
C7B—O3B—C10B—C11B179.56 (17)C1A—C2A—C3A—C4A0.2 (4)
C12B—C11B—C10B—O4B170.2 (2)C1B—C2B—C3B—C4B0.6 (4)
C16B—C11B—C10B—O4B10.1 (3)C6A—C5A—C4A—C3A0.4 (3)
C12B—C11B—C10B—O3B8.8 (3)C2A—C3A—C4A—C5A0.5 (4)
C16B—C11B—C10B—O3B170.85 (19)C6B—C5B—C4B—C3B0.3 (4)
C1A—O1A—C9A—O2A178.64 (19)C2B—C3B—C4B—C5B0.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5A—H5A···O4B0.932.553.389 (3)151
C8A—H8A···O2Bi0.932.523.453 (3)177
C8B—H8B···O2Ai0.932.503.425 (3)176
C12A—H12A···O2Ai0.932.593.498 (3)167
Symmetry code: (i) x, y, z.

Experimental details

Crystal data
Chemical formulaC17H12O4
Mr280.27
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)9.2790 (5), 10.7696 (5), 14.5758 (9)
α, β, γ (°)95.274 (2), 97.875 (2), 104.788 (5)
V3)1382.75 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.35 × 0.20 × 0.20
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16045, 6907, 3981
Rint0.055
(sin θ/λ)max1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.071, 0.193, 1.02
No. of reflections6907
No. of parameters381
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.18

Computer programs: COLLECT (Hooft, 1998), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008), publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5A—H5A···O4B0.932.553.389 (3)151.0
C8A—H8A···O2Bi0.932.523.453 (3)176.7
C8B—H8B···O2Ai0.932.503.425 (3)175.8
C12A—H12A···O2Ai0.932.593.498 (3)166.5
Symmetry code: (i) x, y, z.
 

Acknowledgements

The authors thank the Spectropôle Service of the Faculty of Sciences and Techniques of Saint Jérôme (France) for the use of the diffractometer.

References

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Volume 69| Part 7| July 2013| Pages o1081-o1082
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