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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 11| November 2014| Pages 451-453
doi:10.1107/S1600536814023678

Crystal structure of 4-methyl-7-prop­­oxy-2H-chromen-2-one

Samuel Estrada-Soto,a Amanda Sánchez-Recillas,a Gabriel Navarrete-Vázqueza and Hugo Tlahuextb*

aFacultad de Farmacia, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001 Col. Chamilpa CP 62100, Cuernavaca Mor., México, and bCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001 Col., Chamilpa, CP 62100, Cuernavaca Mor., México
*Correspondence e-mail: tlahuext@uaem.mx

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 15 October 2014; accepted 27 October 2014; online 31 October 2014)

The asymmetric unit of the title compound, C13H14O3, contains two independent mol­ecules, A and B, that are inter­connected through an offset π–π inter­action [inter-centroid separation = 3.6087 (4) Å]. The fused benzene and pyran-2-one rings in each mol­ecule are essentially coplanar, having dihedral angles of 1.22 (12) and 1.57 (12)° for mol­ecules A and B, respectively. Similarly, the coumarin ring system and the 7-prop­oxy substituent are close to being coplanar [C—C—O—C torsion angles = 2.9 (2) and 1.4 (2)° for mol­ecules A and B, respectively]. In the crystal, the mol­ecules are connected by C—H⋯O hydrogen bonds, forming supra­molecular tapes along [100] that are linked into a three-dimensional network by C—H⋯π inter­actions, as well as by the aforementioned π–π inter­actions.

CCDC reference: 1031270

1. Chemical context

Coumarin (2H-1-benzo­pyran-2-one) is a plant-derived natural product known for its pharmacological properties such as anti-inflammatory, anti­coagulant, anti­bacterial, anti­fungal, anti­viral, anti­cancer, anti­hypertensive, anti­tubercular, anti­convulsant, anti-adipogenic, anti­hyperglycemic, anti-oxidant and neuroprotective properties. Dietary exposure to benzopyrones is significant as these compounds are found in vegetables, fruits, seeds, nuts, coffee, tea and wine (Venugopala et al., 2013[Venugopala, K. N., Rashmi, V. & Odhav, B. (2013). Biomed. Res. Int. pp. 1-14.]). In order to assist our knowledge about the stereoelectronic requirements from these kinds of mol­ecules to show anti-asthmatic or tracheal relaxant actions, we have synthesized (Sánchez-Recillas et al., 2014[Sánchez-Recillas, A., Navarrete-Vázquez, G., Hidalgo-Figueroa, S., Rios, M. Y., Ibarra-Barajas, M. & Estrada-Soto, S. (2014). Eur. J. Med. Chem. 77, 400-408.]) and determined the crystal structure of the title compound, (I)[link]. A related structure, 3-acetyl­coumarin, has been reported on by Munshi et al. (2004[Munshi, P., Venugopala, K. N., Jayashree, B. S. & Guru Row, T. N. (2004). Cryst. Growth Des. 4, 1105-1107.]).

[Scheme 1]

2. Structural commentary

The asymmetric unit of (I)[link] contains two independent mol­ecules (A and B)[link]. Bond lengths between equivalent non-H atoms of each mol­ecule are similar, with differences less than 3 s.u.

[Figure 1]
Figure 1
The mol­ecular structure of (I)[link], showing the atom-labelling scheme and the offset π–π inter­action. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. The dashed line indicates the inter­action between the benzene ring centroids Cg1 (C4—C9) and Cg2 (C17—C22).

The fused aryl and pyran-2-one rings in each mol­ecule are individually planar (r.m.s. deviations < 0.0064 for aryl rings and < 0.0141 Å for pyran-2-one rings) and form single planar units [r.m.s. deviation = 0.0159 Å, dihedral angle between the two six-membered rings of 1.22 (12)° in mol­ecule A; r.m.s. deviation = 0.0192 Å, dihedral angle between the two six-membered rings of 1.57 (12)° for B].

The torsion angles between the coumarin ring systems and the 7-prop­oxy substituents in A (C7—C6—O3—C10) and B (C20—C19—O6—C23) are 2.9 (2) and 1.4 (2)°, respectively. The two independent mol­ecules are inter­connected through an offset π–π inter­action, with a distance between the centroids of the C4–C9 and C17–C22 benzene rings of 3.6087 (4) Å.

3. Supra­molecular features

The packing is mainly through C—H⋯O and C—H⋯π hydrogen bonding (Table 1[link]) as well as the π–π inter­action mentioned above. Three B mol­ecules are connected through two pairs of C—H⋯O hydrogen bonds, generating two centrosymmetric R22(8) graph sets; the first involving atoms (⋯H15–C15–C14–O5⋯)2 and the second involving atoms (⋯H18–C18–C19–O6⋯)2. The R22(8) motifs are connected with A mol­ecules through C—H⋯O contacts, generating a tape-like structure along [100] (Fig. 2[link]). Additional, C—H⋯π inter­actions provide the links between neighboring tapes, resulting in a three-dimensional network (Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the O1/C1–C3/C8/C9, C17–C22 and O4/C14–C16/C21/C22 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5⋯O5i 0.95 2.57 3.296 (2) 133
C15—H15⋯O5ii 0.95 2.49 3.422 (2) 165
C18—H18⋯O6iii 0.95 2.45 3.402 (2) 175
C11—H11A⋯Cg2iv 0.99 2.76 3.6087 (4) 140
C24—H24A⋯Cg4v 0.99 2.81 3.613 (2) 139
C23—H23B⋯Cg3v 0.99 2.75 3.614 (2) 145
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+1, -z; (iii) -x, -y+1, -z+1; (iv) -x+1, -y+2, -z; (v) -x+1, -y+1, -z+1.
[Figure 2]
Figure 2
View of the supra­molecular tape structure along [100] sustained by C—H⋯O hydrogen bonds (dashed lines).
[Figure 3]
Figure 3
View of the C—H⋯π hydrogen bonds (dashed lines) between neighbouring tapes. Cg2′, Cg3′ [symmetry code: (′) −x + 1, −y + 2, −z] and Cg4′ [symmetry code: (′) −x + 1, −y + 1, −z + 1].

4. Synthesis and crystallization

The title compound was prepared by SN2 reaction between 7-hy­droxy-4-methyl-2H-chromen-2-one and n-propyl bromide. 7-Hy­droxy-4-methyl-2H-chromen-2-one (0.4 g, 2.27 mmol) and potassium carbonate (1.28 g, 9.30 mmol, 4.1 equiv) were dissolved in acetone (2.0 ml) and kept at room temperature. After 20 minutes, n-propyl­bromide (0.641 ml, 7.03 mmol) was added drop wise and the reaction mixture was heated to reflux (313 K) and monitored by TLC. After completion of the reaction (six days), the reaction mixture was filtered and the solid residue was washed off with cold water (10 ml). The total mother liquors were concentrated under reduced pressure and then poured into water and extracted with ethyl acetate (3 × 15 ml). The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to give a white-coloured solid (m.p. 347.55–348.35 K). Single crystals were obtained from methanol. 1H NMR data (400 MHz; CDCl3: Me4Si) d: 1.02 (3H, t, CH3), 1.82 (2H, m, CH2), 2.36 (3H, s, CH3), 3.94 (2H, t, CH2—O), 6.08 (s, 1H, H-3), 6.76 (1H, d H, J =2.4 Hz, H-8), 6.82 (1H, dd, CH, J = 8.8 Hz, J = 2.4 Hz, H-6), 7.45 (1H, d, CH, J = 8.8 Hz, H-5).

4.1. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. H atoms were positioned geometrically and constrained using the riding-model approximation [C—Har­yl = 0.95 Å, Uiso(Har­yl) = 1.2 Ueq(C); C—Hmethyl­ene = 0.99 Å, Uiso(Hmethyl­ene) = 1.2 Ueq(C); C—Hmeth­yl = 0.98 Å, Uiso(Hmethyl) = 1.5 Ueq(C)].

Table 2
Experimental details

Crystal data
Chemical formula C13H14O3
Mr 218.24
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 7.2418 (9), 11.5459 (14), 14.5301 (17)
α, β, γ (°) 69.014 (2), 76.086 (2), 84.124 (2)
V (Å3) 1100.9 (2)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.25 × 0.25 × 0.21
 
Data collection
Diffractometer Bruker SMART APEX CCD area detector
Absorption correction Multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.])
Tmin, Tmax 0.977, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections 9469, 3872, 3420
Rint 0.030
(sin θ/λ)max (Å−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.122, 1.12
No. of reflections 3872
No. of parameters 293
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.22, −0.25
Computer programs: SMART (Bruker, 2000[Bruker (2000). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus for Windows NT. Bruker AXS Inc., Madison, Wisconsin, USA.]), DIAMOND (Brandenburg, 1997[Brandenburg, K. (1997). DIAMOND. Crystal Impact GbR, Bonn, Germany.]), SHELXTL-NT (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1031270

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814023678/tk5346sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814023678/tk5346Isup2.hkl

checkCIF report


Chemical context top

Coumarin (2H-1-benzo­pyran-2-one) is a plant-derived natural product known for its pharmacological properties such as anti-inflammatory, anti­coagulant, anti­bacterial, anti­fungal, anti­viral, anti­cancer, anti­hypertensive, anti­tubercular, anti­convulsant, anti-adipogenic, anti­hyperglycemic, anti-oxidant and neuroprotective properties. Dietary exposure to benzopyrones is significant as these compounds are found in vegetables, fruits, seeds, nuts, coffee, tea and wine (Venugopala et al., 2013). In order to assist our knowledge about the stereoelectronic requirements from these kinds of molecules to show anti-asthmatic or tracheal relaxant actions, we have synthesized (Sánchez-Recillas et al., 2014) and determined the crystal structure of the title compound, (I). A related structure, 3-acetyl­coumarin, is reported by Munshi et al. (2004).

Structural commentary top

The asymmetric unit of (I) contains two independent molecules (A and B). Bond lengths between equivalent non-H atoms of each molecule are similar, with differences less than 3 s.u.

The fused aryl and pyran-2-one rings in each molecule are individually planar (r.m.s. deviations < 0.0064 for aryl rings and < 0.0141 Å for pyran-2-one rings) and form single planar units [r.m.s. deviation = 0.0159 Å, dihedral angle between the two six-membered rings of 1.22 (12)° in molecule A; r.m.s. deviation = 0.0192 Å, dihedral angle between the two six-membered rings of 1.57 (12)° for B].

The torsion angles between the coumarins ring systems and the 7-prop­oxy substituents in A (C7—C6—O3—C10) and B (C20—C19—O6—C23) are 2.9 (2) and 1.4 (2)°, respectively. The two independent molecules are inter­connected through an offset π–π inter­action, with a distance between the centroids of the C4–C9 and C17–C22 benzene rings of 3.6087 (4) Å.

Supra­molecular features top

The packing is mainly through C—H···O and C—H···π hydrogen bonding (Table 1) as well as the π–π inter­action mentioned above. Three B molecules are connected through two pairs of C—H···O hydrogen bonds, generating two centrosymmetric R22(8) graph sets; the first involving atoms (···H15–C15–C14–O5···)2 and the second involving atoms (···H18–C18–C19–O6···)2. The R22(8) motifs are connected with A molecules through C—H···O contacts, generating a tape-like structure along [100] (Fig. 2). Additional, C—H···π inter­actions provide the links between neighboring tapes, resulting in a three-dimensional network (Fig. 3).

Synthesis and crystallization top

The title compound was prepared by SN2 reaction between 7-hy­droxy-4-methyl-2H-chromen-2-one and n-propyl bromide. 7-Hy­droxy-4-methyl-2H-chromen-2-one (0.4 g, 2.27 mmol) and potassium carbonate (1.28 g, 9.30 mmol, 4.1 equiv) were dissolved in acetone (2.0 ml) and kept at room temperature. After 20 minutes, n-propyl­bromide (0.641 ml, 7.03 mmol) was added drop wise and the reaction mixture was heated to reflux (313 K) and monitored by TLC. After completion of the reaction (six days), the reaction mixture was filtered and the solid residue was washed off with cold water (10 ml). The total mother liquors were concentrated under reduced pressure and then poured into water and extracted with ethyl acetate (3 × 15 ml). The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to give a white-coloured solid (m.p. 347.55–348.35 K). Single crystals were obtained from methanol. 1H NMR data (400 MHz; CDCl3: Me4Si) d: 1.02 (3H, t, CH3), 1.82 (2H, m, CH2), 2.36 (3H, s, CH3), 3.94 (2H, t, CH2—O), 6.08 (s, 1H, H-3), 6.76 (1H, d H, J =2.4 Hz, H-8), 6.82 (1H, dd, CH, J = 8.8 Hz, J = 2.4 Hz, H-6), 7.45 (1H, d, CH, J = 8.8 Hz, H-5).

Refinement top

H atoms were positioned geometrically and constrained using the riding-model approximation [C—Haryl = 0.95 Å, Uiso(Haryl) = 1.2 Ueq(C); C—Hmethyl­ene = 0.99 Å, Uiso(Hmethyl­ene) = 1.2 Ueq(C); C-Hmethyl = 0.98 Å, Uiso(Hmethyl) = 1.5 Ueq(C)].

Related literature top

For a biological and crystallographic studies on related coumarins, see: Munshi et al. (2004); Sánchez-Recillas et al. (2014); Venugopala et al. (2013).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008); program(s) used to refine structure: SHELXTL-NT (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1997); software used to prepare material for publication: SHELXTL-NT (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
The molecular structure of (I), showing the atom-labelling scheme and the offset π–π interaction. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. The dashed line indicates the interaction between the benzene ring centroids Cg1 (C4—C9) and Cg2 (C17—C22).

View of the supramolecular tape structure along [100] sustained by C—H···O hydrogen bonds (dashed lines).

View of the C—H···π hydrogen bonds (dashed lines) between neighbouring tapes. Cg2', Cg3' [symmetry code: (') -x+1, -y+2, -z] and Cg4' [symmetry code: (') -x+1, -y+1, -z+1].
4-Methyl-7-propoxy-2H-chromen-2-one top
Crystal data top
C13H14O3Z = 4
Mr = 218.24F(000) = 464
Triclinic, P1Dx = 1.317 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2418 (9) ÅCell parameters from 7718 reflections
b = 11.5459 (14) Åθ = 2.8–28.2°
c = 14.5301 (17) ŵ = 0.09 mm−1
α = 69.014 (2)°T = 100 K
β = 76.086 (2)°Block, colourless
γ = 84.124 (2)°0.25 × 0.25 × 0.21 mm
V = 1100.9 (2) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		3872 independent reflections
Radiation source: fine-focus sealed tube3420 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 8.3 pixels mm-1θmax = 25.0°, θmin = 1.5°
ϕ and ω scansh = −8→8
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		k = −13→13
Tmin = 0.977, Tmax = 0.981l = −17→17
9469 measured reflections
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0454P)2 + 0.5831P]
where P = (Fo2 + 2Fc2)/3
3872 reflections(Δ/σ)max = 0.001
293 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C13H14O3γ = 84.124 (2)°
Mr = 218.24V = 1100.9 (2) Å3
Triclinic, P1Z = 4
a = 7.2418 (9) ÅMo Kα radiation
b = 11.5459 (14) ŵ = 0.09 mm−1
c = 14.5301 (17) ÅT = 100 K
α = 69.014 (2)°0.25 × 0.25 × 0.21 mm
β = 76.086 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		3872 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		3420 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.981Rint = 0.030
9469 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.12Δρmax = 0.22 e Å−3
3872 reflectionsΔρmin = −0.25 e Å−3
293 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2312 (2)1.02587 (16)0.34492 (13)0.0272 (4)
C20.0602 (2)0.95556 (16)0.37805 (13)0.0274 (4)
H2−0.03540.96660.43200.033*
C30.0295 (2)0.87428 (16)0.33576 (13)0.0269 (4)
C40.1609 (3)0.77466 (16)0.20345 (13)0.0269 (4)
H40.04730.72970.22120.032*
C50.3071 (2)0.75950 (16)0.12847 (13)0.0265 (4)
H50.29370.70480.09480.032*
C60.4758 (2)0.82451 (15)0.10153 (12)0.0253 (4)
C70.4952 (2)0.90553 (15)0.14979 (12)0.0248 (4)
H70.60910.95040.13170.030*
C80.3444 (2)0.91946 (15)0.22501 (12)0.0235 (4)
C90.1753 (2)0.85505 (15)0.25466 (12)0.0240 (4)
C100.7927 (2)0.86097 (16)−0.00035 (13)0.0281 (4)
H10A0.85280.83480.05860.034*
H10B0.77420.9522−0.02300.034*
C110.9176 (3)0.82336 (17)−0.08476 (13)0.0295 (4)
H11A0.85680.8502−0.14340.035*
H11B0.93290.7319−0.06200.035*
C121.1119 (3)0.88242 (19)−0.11598 (14)0.0347 (4)
H12A1.09660.9729−0.13940.052*
H12B1.19190.8573−0.17070.052*
H12C1.17240.8550−0.05800.052*
C13−0.1524 (3)0.80431 (18)0.37212 (14)0.0346 (4)
H13A−0.23050.82330.43030.052*
H13B−0.12370.71510.39210.052*
H13C−0.22190.82880.31770.052*
C140.8545 (2)0.54134 (16)0.14392 (12)0.0250 (4)
C150.7477 (2)0.46641 (15)0.11512 (12)0.0253 (4)
H150.80640.44000.05990.030*
C160.5668 (2)0.43214 (15)0.16371 (12)0.0252 (4)
C170.2919 (2)0.44277 (16)0.30600 (13)0.0255 (4)
H170.21940.38910.29240.031*
C180.2136 (2)0.48829 (15)0.38246 (13)0.0254 (4)
H180.08810.46650.42080.030*
C190.3192 (2)0.56707 (15)0.40370 (12)0.0232 (4)
C200.5028 (2)0.59811 (15)0.34929 (12)0.0230 (4)
H200.57550.65070.36390.028*
C210.5781 (2)0.55004 (15)0.27239 (12)0.0224 (4)
C220.4766 (2)0.47361 (14)0.24749 (12)0.0223 (4)
C230.3305 (2)0.69312 (16)0.50284 (13)0.0250 (4)
H23A0.36470.76850.44260.030*
H23B0.44910.65260.52260.030*
C240.2037 (3)0.72763 (16)0.58868 (13)0.0280 (4)
H24A0.17090.65190.64890.034*
H24B0.08410.76640.56900.034*
C250.3047 (3)0.81783 (18)0.61425 (14)0.0357 (4)
H25A0.42440.77990.63220.054*
H25B0.22320.83730.67140.054*
H25C0.33150.89430.55550.054*
C260.4575 (3)0.35469 (17)0.13210 (14)0.0324 (4)
H26A0.53530.33880.07250.049*
H26B0.34020.39910.11580.049*
H26C0.42550.27570.18740.049*
O10.37241 (17)1.00201 (11)0.26973 (9)0.0264 (3)
O20.26525 (19)1.10374 (12)0.37645 (10)0.0359 (3)
O30.61273 (17)0.80147 (11)0.02699 (9)0.0291 (3)
O40.76161 (16)0.58432 (11)0.22148 (8)0.0243 (3)
O51.01862 (17)0.57246 (12)0.10667 (9)0.0315 (3)
O60.22868 (16)0.60943 (11)0.48005 (9)0.0266 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0281 (9)0.0300 (9)0.0229 (8)0.0023 (7)−0.0038 (7)−0.0103 (7)
C20.0273 (9)0.0319 (9)0.0217 (8)0.0009 (7)−0.0034 (7)−0.0093 (7)
C30.0267 (9)0.0288 (9)0.0214 (8)0.0006 (7)−0.0061 (7)−0.0039 (7)
C40.0294 (9)0.0264 (9)0.0245 (9)−0.0029 (7)−0.0089 (7)−0.0058 (7)
C50.0315 (9)0.0253 (8)0.0250 (9)−0.0007 (7)−0.0107 (7)−0.0086 (7)
C60.0286 (9)0.0270 (9)0.0192 (8)0.0025 (7)−0.0052 (7)−0.0074 (7)
C70.0263 (9)0.0271 (9)0.0211 (8)−0.0010 (7)−0.0046 (7)−0.0088 (7)
C80.0286 (9)0.0234 (8)0.0203 (8)0.0007 (7)−0.0083 (7)−0.0080 (7)
C90.0252 (8)0.0248 (8)0.0209 (8)−0.0009 (7)−0.0070 (7)−0.0052 (7)
C100.0288 (9)0.0300 (9)0.0256 (9)0.0003 (7)−0.0048 (7)−0.0108 (7)
C110.0329 (10)0.0323 (9)0.0222 (9)0.0026 (7)−0.0047 (7)−0.0100 (7)
C120.0331 (10)0.0464 (11)0.0256 (9)0.0030 (8)−0.0063 (8)−0.0147 (8)
C130.0295 (10)0.0400 (11)0.0313 (10)−0.0058 (8)−0.0032 (8)−0.0095 (8)
C140.0265 (9)0.0283 (9)0.0181 (8)0.0021 (7)−0.0005 (7)−0.0089 (7)
C150.0284 (9)0.0276 (9)0.0201 (8)0.0010 (7)−0.0023 (7)−0.0106 (7)
C160.0285 (9)0.0250 (8)0.0210 (8)0.0001 (7)−0.0038 (7)−0.0079 (7)
C170.0252 (9)0.0266 (8)0.0251 (9)−0.0019 (7)−0.0040 (7)−0.0101 (7)
C180.0232 (8)0.0270 (9)0.0236 (8)−0.0028 (7)0.0002 (7)−0.0088 (7)
C190.0242 (8)0.0253 (8)0.0180 (8)0.0017 (6)−0.0002 (6)−0.0086 (6)
C200.0241 (8)0.0239 (8)0.0206 (8)−0.0009 (7)−0.0022 (7)−0.0087 (7)
C210.0197 (8)0.0237 (8)0.0193 (8)0.0001 (6)−0.0006 (6)−0.0047 (6)
C220.0234 (8)0.0224 (8)0.0201 (8)0.0002 (6)−0.0029 (7)−0.0076 (7)
C230.0251 (8)0.0279 (9)0.0229 (8)−0.0001 (7)−0.0038 (7)−0.0108 (7)
C240.0298 (9)0.0329 (9)0.0212 (8)0.0052 (7)−0.0038 (7)−0.0120 (7)
C250.0441 (11)0.0377 (10)0.0306 (10)0.0074 (9)−0.0113 (8)−0.0182 (8)
C260.0341 (10)0.0368 (10)0.0293 (10)−0.0038 (8)−0.0030 (8)−0.0169 (8)
O10.0283 (6)0.0305 (6)0.0229 (6)−0.0031 (5)−0.0023 (5)−0.0136 (5)
O20.0382 (7)0.0401 (7)0.0359 (7)−0.0036 (6)−0.0031 (6)−0.0232 (6)
O30.0304 (7)0.0333 (7)0.0250 (6)−0.0018 (5)−0.0018 (5)−0.0142 (5)
O40.0210 (6)0.0302 (6)0.0208 (6)−0.0024 (5)0.0024 (5)−0.0118 (5)
O50.0252 (7)0.0418 (7)0.0267 (7)−0.0050 (5)0.0036 (5)−0.0158 (6)
O60.0242 (6)0.0336 (7)0.0238 (6)−0.0030 (5)0.0018 (5)−0.0158 (5)
Geometric parameters (Å, º) top
C1—O21.214 (2)C14—O51.214 (2)
C1—O11.391 (2)C14—O41.3916 (19)
C1—C21.437 (2)C14—C151.440 (2)
C2—C31.353 (3)C15—C161.353 (2)
C2—H20.9500C15—H150.9500
C3—C91.447 (2)C16—C221.452 (2)
C3—C131.498 (2)C16—C261.501 (2)
C4—C51.372 (2)C17—C181.373 (2)
C4—C91.406 (2)C17—C221.405 (2)
C4—H40.9500C17—H170.9500
C5—C61.399 (2)C18—C191.402 (2)
C5—H50.9500C18—H180.9500
C6—O31.365 (2)C19—O61.3685 (19)
C6—C71.390 (2)C19—C201.382 (2)
C7—C81.389 (2)C20—C211.394 (2)
C7—H70.9500C20—H200.9500
C8—O11.385 (2)C21—O41.3769 (19)
C8—C91.394 (2)C21—C221.392 (2)
C10—O31.438 (2)C23—O61.442 (2)
C10—C111.510 (2)C23—C241.513 (2)
C10—H10A0.9900C23—H23A0.9900
C10—H10B0.9900C23—H23B0.9900
C11—C121.523 (3)C24—C251.524 (3)
C11—H11A0.9900C24—H24A0.9900
C11—H11B0.9900C24—H24B0.9900
C12—H12A0.9800C25—H25A0.9800
C12—H12B0.9800C25—H25B0.9800
C12—H12C0.9800C25—H25C0.9800
C13—H13A0.9800C26—H26A0.9800
C13—H13B0.9800C26—H26B0.9800
C13—H13C0.9800C26—H26C0.9800
O2—C1—O1116.67 (16)O4—C14—C15117.51 (14)
O2—C1—C2126.41 (16)C16—C15—C14122.54 (15)
O1—C1—C2116.92 (15)C16—C15—H15118.7
C3—C2—C1122.82 (16)C14—C15—H15118.7
C3—C2—H2118.6C15—C16—C22118.65 (16)
C1—C2—H2118.6C15—C16—C26121.73 (15)
C2—C3—C9119.15 (16)C22—C16—C26119.61 (15)
C2—C3—C13120.81 (16)C18—C17—C22121.56 (16)
C9—C3—C13120.03 (16)C18—C17—H17119.2
C5—C4—C9121.63 (16)C22—C17—H17119.2
C5—C4—H4119.2C17—C18—C19119.83 (15)
C9—C4—H4119.2C17—C18—H18120.1
C4—C5—C6119.99 (16)C19—C18—H18120.1
C4—C5—H5120.0O6—C19—C20123.65 (15)
C6—C5—H5120.0O6—C19—C18115.75 (14)
O3—C6—C7124.58 (16)C20—C19—C18120.60 (15)
O3—C6—C5115.22 (15)C19—C20—C21118.08 (16)
C7—C6—C5120.20 (16)C19—C20—H20121.0
C8—C7—C6118.48 (16)C21—C20—H20121.0
C8—C7—H7120.8O4—C21—C22121.81 (14)
C6—C7—H7120.8O4—C21—C20115.06 (15)
O1—C8—C7115.64 (15)C22—C21—C20123.13 (15)
O1—C8—C9121.49 (15)C21—C22—C17116.77 (15)
C7—C8—C9122.87 (16)C21—C22—C16118.50 (15)
C8—C9—C4116.82 (16)C17—C22—C16124.73 (15)
C8—C9—C3118.18 (15)O6—C23—C24108.36 (13)
C4—C9—C3125.00 (16)O6—C23—H23A110.0
O3—C10—C11107.78 (14)C24—C23—H23A110.0
O3—C10—H10A110.2O6—C23—H23B110.0
C11—C10—H10A110.2C24—C23—H23B110.0
O3—C10—H10B110.2H23A—C23—H23B108.4
C11—C10—H10B110.2C23—C24—C25110.15 (15)
H10A—C10—H10B108.5C23—C24—H24A109.6
C10—C11—C12110.13 (15)C25—C24—H24A109.6
C10—C11—H11A109.6C23—C24—H24B109.6
C12—C11—H11A109.6C25—C24—H24B109.6
C10—C11—H11B109.6H24A—C24—H24B108.1
C12—C11—H11B109.6C24—C25—H25A109.5
H11A—C11—H11B108.1C24—C25—H25B109.5
C11—C12—H12A109.5H25A—C25—H25B109.5
C11—C12—H12B109.5C24—C25—H25C109.5
H12A—C12—H12B109.5H25A—C25—H25C109.5
C11—C12—H12C109.5H25B—C25—H25C109.5
H12A—C12—H12C109.5C16—C26—H26A109.5
H12B—C12—H12C109.5C16—C26—H26B109.5
C3—C13—H13A109.5H26A—C26—H26B109.5
C3—C13—H13B109.5C16—C26—H26C109.5
H13A—C13—H13B109.5H26A—C26—H26C109.5
C3—C13—H13C109.5H26B—C26—H26C109.5
H13A—C13—H13C109.5C8—O1—C1121.32 (13)
H13B—C13—H13C109.5C6—O3—C10117.68 (13)
O5—C14—O4115.87 (15)C21—O4—C14120.86 (13)
O5—C14—C15126.62 (15)C19—O6—C23117.62 (13)
O2—C1—C2—C3176.86 (18)O6—C19—C20—C21−179.18 (14)
O1—C1—C2—C3−3.6 (3)C18—C19—C20—C210.7 (2)
C1—C2—C3—C91.0 (3)C19—C20—C21—O4−179.80 (14)
C1—C2—C3—C13−179.20 (16)C19—C20—C21—C220.6 (3)
C9—C4—C5—C60.2 (3)O4—C21—C22—C17178.73 (14)
C4—C5—C6—O3179.21 (15)C20—C21—C22—C17−1.7 (2)
C4—C5—C6—C7−0.7 (3)O4—C21—C22—C16−1.6 (2)
O3—C6—C7—C8−179.56 (14)C20—C21—C22—C16177.96 (15)
C5—C6—C7—C80.3 (2)C18—C17—C22—C211.5 (2)
C6—C7—C8—O1−179.66 (14)C18—C17—C22—C16−178.13 (16)
C6—C7—C8—C90.5 (3)C15—C16—C22—C211.9 (2)
O1—C8—C9—C4179.26 (14)C26—C16—C22—C21−177.11 (15)
C7—C8—C9—C4−0.9 (2)C15—C16—C22—C17−178.45 (16)
O1—C8—C9—C3−1.4 (2)C26—C16—C22—C172.6 (3)
C7—C8—C9—C3178.37 (15)O6—C23—C24—C25−179.12 (14)
C5—C4—C9—C80.5 (2)C7—C8—O1—C1178.93 (14)
C5—C4—C9—C3−178.70 (16)C9—C8—O1—C1−1.2 (2)
C2—C3—C9—C81.5 (2)O2—C1—O1—C8−176.75 (15)
C13—C3—C9—C8−178.27 (16)C2—C1—O1—C83.6 (2)
C2—C3—C9—C4−179.23 (16)C7—C6—O3—C102.9 (2)
C13—C3—C9—C41.0 (3)C5—C6—O3—C10−176.98 (14)
O3—C10—C11—C12−179.21 (14)C11—C10—O3—C6−178.95 (13)
O5—C14—C15—C16177.33 (17)C22—C21—O4—C14−1.3 (2)
O4—C14—C15—C16−3.4 (2)C20—C21—O4—C14179.11 (14)
C14—C15—C16—C220.6 (3)O5—C14—O4—C21−176.94 (14)
C14—C15—C16—C26179.60 (16)C15—C14—O4—C213.7 (2)
C22—C17—C18—C19−0.3 (3)C20—C19—O6—C231.4 (2)
C17—C18—C19—O6179.01 (14)C18—C19—O6—C23−178.55 (14)
C17—C18—C19—C20−0.9 (3)C24—C23—O6—C19179.83 (13)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg3 and Cg4 are the centroids of the O1/C1–C3/C8/C9, C17–C22 and O4/C14–C16/C21/C22 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C5—H5···O5i0.952.573.296 (2)133
C15—H15···O5ii0.952.493.422 (2)165
C18—H18···O6iii0.952.453.402 (2)175
C11—H11A···Cg2iv0.992.763.6087 (4)140
C24—H24A···Cg4v0.992.813.613 (2)139
C23—H23B···Cg3v0.992.753.614 (2)145
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+2, −z; (v) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
Cg2, Cg3 and Cg4 are the centroids of the O1/C1–C3/C8/C9, C17–C22 and O4/C14–C16/C21/C22 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C5—H5···O5i0.952.573.296 (2)133
C15—H15···O5ii0.952.493.422 (2)165
C18—H18···O6iii0.952.453.402 (2)175
C11—H11A···Cg2iv0.992.763.6087 (4)140
C24—H24A···Cg4v0.992.813.613 (2)139
C23—H23B···Cg3v0.992.753.614 (2)145
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+2, −z; (v) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC13H14O3
Mr218.24
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.2418 (9), 11.5459 (14), 14.5301 (17)
α, β, γ (°)69.014 (2), 76.086 (2), 84.124 (2)
V (Å3)1100.9 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.25 × 0.25 × 0.21
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.977, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections		9469, 3872, 3420
Rint0.030
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.122, 1.12
No. of reflections3872
No. of parameters293
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.22, −0.25

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2001), DIAMOND (Brandenburg, 1997), SHELXTL-NT (Sheldrick, 2008) and publCIF (Westrip, 2010).

 

Acknowledgements

This work was supported by the Consejo Nacional de Ciencia y Tecnología (CONACyT) under grant No. 167044.

References

First citationBrandenburg, K. (1997). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2000). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2001). SAINT-Plus for Windows NT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationMunshi, P., Venugopala, K. N., Jayashree, B. S. & Guru Row, T. N. (2004). Cryst. Growth Des. 4, 1105–1107.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSánchez-Recillas, A., Navarrete-Vázquez, G., Hidalgo-Figueroa, S., Rios, M. Y., Ibarra-Barajas, M. & Estrada-Soto, S. (2014). Eur. J. Med. Chem. 77, 400–408.  PubMed Google Scholar
 First citationSheldrick, G. M. (2003). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationVenugopala, K. N., Rashmi, V. & Odhav, B. (2013). Biomed. Res. Int. pp. 1–14.  Web of Science CrossRef Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 11| November 2014| Pages 451-453
doi:10.1107/S1600536814023678
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