Chemical context   {#sec1}
==================

Coumarin (2*H*-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[@bb8]). 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[@bb5]) and determined the crystal structure of the title compound, (I)[](#scheme1){ref-type="chem"}. A related structure, 3-acetyl­coumarin, has been reported on by Munshi *et al.* (2004[@bb4]).

Structural commentary   {#sec2}
=======================

The asymmetric unit of (I)[](#scheme1){ref-type="chem"} 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   {#sec3}
==========================

The packing is mainly through C---H⋯O and C---H⋯π hydrogen bonding (Table 1[▶](#table1){ref-type="table"}) 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 (8) graph sets; the first involving atoms (⋯H15--C15--C14--O5⋯)~2~ and the second involving atoms (⋯H18--C18--C19--O6⋯)~2.~ The (8) motifs are connected with *A* mol­ecules through C---H⋯O contacts, generating a tape-like structure along \[100\] (Fig. 2[▶](#fig2){ref-type="fig"}). Additional, C---H⋯π inter­actions provide the links between neighboring tapes, resulting in a three-dimensional network (Fig. 3[▶](#fig3){ref-type="fig"}).

Synthesis and crystallization   {#sec4}
===============================

The title compound was prepared by *SN*2 reaction between 7-hy­droxy-4-methyl-2*H*-chromen-2-one and *n*-propyl bromide. 7-Hy­droxy-4-methyl-2*H*-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 Na~2~SO~4~ and evaporated under reduced pressure to give a white-coloured solid (m.p. 347.55--348.35 K). Single crystals were obtained from methanol. ^1^H NMR data (400 MHz; CDCl~3~: Me~4~Si) *d*: 1.02 (3*H*, *t*, CH~3~), 1.82 (2*H*, *m*, CH~2~), 2.36 (3*H*, *s*, CH~3~), 3.94 (2*H*, *t*, CH~2~---O), 6.08 (*s*, 1H, H-3), 6.76 (1*H*, *d* H, *J =*2.4 Hz, H-8), 6.82 (1*H*, *dd*, CH, *J =* 8.8 Hz, *J =* 2.4 Hz, H-6), 7.45 (1*H*, *d*, CH, *J =* 8.8 Hz, H-5).

Refinement   {#sec4.1}
------------

Crystal data, data collection and structure refinement details are summarized in Table 2[▶](#table2){ref-type="table"}. H atoms were positioned geometrically and constrained using the riding-model approximation \[C---H~ar­yl~ = 0.95 Å, *U* ~iso~(H~ar­yl~) = 1.2 *U* ~eq~(C); C---H~methyl­ene~ = 0.99 Å, *U* ~iso~(H~methyl­ene~) = 1.2 *U* ~eq~(C); C---H~meth­yl~ = 0.98 Å, *U* ~iso~(H~methy~l) = 1.5 *U* ~eq~(C)\].

Supplementary Material
======================

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: [10.1107/S1600536814023678/tk5346sup1.cif](http://dx.doi.org/10.1107/S1600536814023678/tk5346sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536814023678/tk5346Isup2.hkl](http://dx.doi.org/10.1107/S1600536814023678/tk5346Isup2.hkl)

CCDC reference: [1031270](http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1031270)

Additional supporting information: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?tk5346&file=tk5346sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?tk5346sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?tk5346&checkcif=yes)

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

Crystal data {#tablewrapcrystaldatalong}
============

  ----------------------- ---------------------------------------
  C~13~H~14~O~3~          *Z* = 4
  *M~r~* = 218.24         *F*(000) = 464
  Triclinic, *P*1         *D*~x~ = 1.317 Mg m^−3^
  Hall symbol: -P 1       Mo *K*α radiation, λ = 0.71073 Å
  *a* = 7.2418 (9) Å      Cell parameters from 7718 reflections
  *b* = 11.5459 (14) Å    θ = 2.8--28.2°
  *c* = 14.5301 (17) Å    µ = 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) Å^3^   
  ----------------------- ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  --------------------------------------------------------------- --------------------------------------
  Bruker SMART APEX CCD area-detector diffractometer              3872 independent reflections
  Radiation source: fine-focus sealed tube                        3420 reflections with *I* \> 2σ(*I*)
  Graphite monochromator                                          *R*~int~ = 0.030
  Detector resolution: 8.3 pixels mm^-1^                          θ~max~ = 25.0°, θ~min~ = 1.5°
  φ and ω scans                                                   *h* = −8→8
  Absorption correction: multi-scan (*SADABS*; Sheldrick, 2003)   *k* = −13→13
  *T*~min~ = 0.977, *T*~max~ = 0.981                              *l* = −17→17
  9469 measured reflections                                       
  --------------------------------------------------------------- --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.047   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.122                  H-atom parameters constrained
  *S* = 1.12                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0454*P*)^2^ + 0.5831*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  3872 reflections                      (Δ/σ)~max~ = 0.001
  293 parameters                        Δρ~max~ = 0.22 e Å^−3^
  0 restraints                          Δρ~min~ = −0.25 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  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 *F*^2^ against ALL reflections. The weighted *R*-factor *wR* and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> σ(*F*^2^) is used only for calculating *R*-factors(gt) *etc*. and is not relevant to the choice of reflections for refinement. *R*-factors based on *F*^2^ 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 (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------ -------------- -------------- --------------- -------------------- --
         *x*            *y*            *z*             *U*~iso~\*/*U*~eq~   
  C1     0.2312 (2)     1.02587 (16)   0.34492 (13)    0.0272 (4)           
  C2     0.0602 (2)     0.95556 (16)   0.37805 (13)    0.0274 (4)           
  H2     −0.0354        0.9666         0.4320          0.033\*              
  C3     0.0295 (2)     0.87428 (16)   0.33576 (13)    0.0269 (4)           
  C4     0.1609 (3)     0.77466 (16)   0.20345 (13)    0.0269 (4)           
  H4     0.0473         0.7297         0.2212          0.032\*              
  C5     0.3071 (2)     0.75950 (16)   0.12847 (13)    0.0265 (4)           
  H5     0.2937         0.7048         0.0948          0.032\*              
  C6     0.4758 (2)     0.82451 (15)   0.10153 (12)    0.0253 (4)           
  C7     0.4952 (2)     0.90553 (15)   0.14979 (12)    0.0248 (4)           
  H7     0.6091         0.9504         0.1317          0.030\*              
  C8     0.3444 (2)     0.91946 (15)   0.22501 (12)    0.0235 (4)           
  C9     0.1753 (2)     0.85505 (15)   0.25466 (12)    0.0240 (4)           
  C10    0.7927 (2)     0.86097 (16)   −0.00035 (13)   0.0281 (4)           
  H10A   0.8528         0.8348         0.0586          0.034\*              
  H10B   0.7742         0.9522         −0.0230         0.034\*              
  C11    0.9176 (3)     0.82336 (17)   −0.08476 (13)   0.0295 (4)           
  H11A   0.8568         0.8502         −0.1434         0.035\*              
  H11B   0.9329         0.7319         −0.0620         0.035\*              
  C12    1.1119 (3)     0.88242 (19)   −0.11598 (14)   0.0347 (4)           
  H12A   1.0966         0.9729         −0.1394         0.052\*              
  H12B   1.1919         0.8573         −0.1707         0.052\*              
  H12C   1.1724         0.8550         −0.0580         0.052\*              
  C13    −0.1524 (3)    0.80431 (18)   0.37212 (14)    0.0346 (4)           
  H13A   −0.2305        0.8233         0.4303          0.052\*              
  H13B   −0.1237        0.7151         0.3921          0.052\*              
  H13C   −0.2219        0.8288         0.3177          0.052\*              
  C14    0.8545 (2)     0.54134 (16)   0.14392 (12)    0.0250 (4)           
  C15    0.7477 (2)     0.46641 (15)   0.11512 (12)    0.0253 (4)           
  H15    0.8064         0.4400         0.0599          0.030\*              
  C16    0.5668 (2)     0.43214 (15)   0.16371 (12)    0.0252 (4)           
  C17    0.2919 (2)     0.44277 (16)   0.30600 (13)    0.0255 (4)           
  H17    0.2194         0.3891         0.2924          0.031\*              
  C18    0.2136 (2)     0.48829 (15)   0.38246 (13)    0.0254 (4)           
  H18    0.0881         0.4665         0.4208          0.030\*              
  C19    0.3192 (2)     0.56707 (15)   0.40370 (12)    0.0232 (4)           
  C20    0.5028 (2)     0.59811 (15)   0.34929 (12)    0.0230 (4)           
  H20    0.5755         0.6507         0.3639          0.028\*              
  C21    0.5781 (2)     0.55004 (15)   0.27239 (12)    0.0224 (4)           
  C22    0.4766 (2)     0.47361 (14)   0.24749 (12)    0.0223 (4)           
  C23    0.3305 (2)     0.69312 (16)   0.50284 (13)    0.0250 (4)           
  H23A   0.3647         0.7685         0.4426          0.030\*              
  H23B   0.4491         0.6526         0.5226          0.030\*              
  C24    0.2037 (3)     0.72763 (16)   0.58868 (13)    0.0280 (4)           
  H24A   0.1709         0.6519         0.6489          0.034\*              
  H24B   0.0841         0.7664         0.5690          0.034\*              
  C25    0.3047 (3)     0.81783 (18)   0.61425 (14)    0.0357 (4)           
  H25A   0.4244         0.7799         0.6322          0.054\*              
  H25B   0.2232         0.8373         0.6714          0.054\*              
  H25C   0.3315         0.8943         0.5555          0.054\*              
  C26    0.4575 (3)     0.35469 (17)   0.13210 (14)    0.0324 (4)           
  H26A   0.5353         0.3388         0.0725          0.049\*              
  H26B   0.3402         0.3991         0.1158          0.049\*              
  H26C   0.4255         0.2757         0.1874          0.049\*              
  O1     0.37241 (17)   1.00201 (11)   0.26973 (9)     0.0264 (3)           
  O2     0.26525 (19)   1.10374 (12)   0.37645 (10)    0.0359 (3)           
  O3     0.61273 (17)   0.80147 (11)   0.02699 (9)     0.0291 (3)           
  O4     0.76161 (16)   0.58432 (11)   0.22148 (8)     0.0243 (3)           
  O5     1.01862 (17)   0.57246 (12)   0.10667 (9)     0.0315 (3)           
  O6     0.22868 (16)   0.60943 (11)   0.48005 (9)     0.0266 (3)           
  ------ -------------- -------------- --------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- ------------- ------------- ------------- ------------- ------------- -------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^       *U*^13^       *U*^23^
  C1    0.0281 (9)    0.0300 (9)    0.0229 (8)    0.0023 (7)    −0.0038 (7)   −0.0103 (7)
  C2    0.0273 (9)    0.0319 (9)    0.0217 (8)    0.0009 (7)    −0.0034 (7)   −0.0093 (7)
  C3    0.0267 (9)    0.0288 (9)    0.0214 (8)    0.0006 (7)    −0.0061 (7)   −0.0039 (7)
  C4    0.0294 (9)    0.0264 (9)    0.0245 (9)    −0.0029 (7)   −0.0089 (7)   −0.0058 (7)
  C5    0.0315 (9)    0.0253 (8)    0.0250 (9)    −0.0007 (7)   −0.0107 (7)   −0.0086 (7)
  C6    0.0286 (9)    0.0270 (9)    0.0192 (8)    0.0025 (7)    −0.0052 (7)   −0.0074 (7)
  C7    0.0263 (9)    0.0271 (9)    0.0211 (8)    −0.0010 (7)   −0.0046 (7)   −0.0088 (7)
  C8    0.0286 (9)    0.0234 (8)    0.0203 (8)    0.0007 (7)    −0.0083 (7)   −0.0080 (7)
  C9    0.0252 (8)    0.0248 (8)    0.0209 (8)    −0.0009 (7)   −0.0070 (7)   −0.0052 (7)
  C10   0.0288 (9)    0.0300 (9)    0.0256 (9)    0.0003 (7)    −0.0048 (7)   −0.0108 (7)
  C11   0.0329 (10)   0.0323 (9)    0.0222 (9)    0.0026 (7)    −0.0047 (7)   −0.0100 (7)
  C12   0.0331 (10)   0.0464 (11)   0.0256 (9)    0.0030 (8)    −0.0063 (8)   −0.0147 (8)
  C13   0.0295 (10)   0.0400 (11)   0.0313 (10)   −0.0058 (8)   −0.0032 (8)   −0.0095 (8)
  C14   0.0265 (9)    0.0283 (9)    0.0181 (8)    0.0021 (7)    −0.0005 (7)   −0.0089 (7)
  C15   0.0284 (9)    0.0276 (9)    0.0201 (8)    0.0010 (7)    −0.0023 (7)   −0.0106 (7)
  C16   0.0285 (9)    0.0250 (8)    0.0210 (8)    0.0001 (7)    −0.0038 (7)   −0.0079 (7)
  C17   0.0252 (9)    0.0266 (8)    0.0251 (9)    −0.0019 (7)   −0.0040 (7)   −0.0101 (7)
  C18   0.0232 (8)    0.0270 (9)    0.0236 (8)    −0.0028 (7)   0.0002 (7)    −0.0088 (7)
  C19   0.0242 (8)    0.0253 (8)    0.0180 (8)    0.0017 (6)    −0.0002 (6)   −0.0086 (6)
  C20   0.0241 (8)    0.0239 (8)    0.0206 (8)    −0.0009 (7)   −0.0022 (7)   −0.0087 (7)
  C21   0.0197 (8)    0.0237 (8)    0.0193 (8)    0.0001 (6)    −0.0006 (6)   −0.0047 (6)
  C22   0.0234 (8)    0.0224 (8)    0.0201 (8)    0.0002 (6)    −0.0029 (7)   −0.0076 (7)
  C23   0.0251 (8)    0.0279 (9)    0.0229 (8)    −0.0001 (7)   −0.0038 (7)   −0.0108 (7)
  C24   0.0298 (9)    0.0329 (9)    0.0212 (8)    0.0052 (7)    −0.0038 (7)   −0.0120 (7)
  C25   0.0441 (11)   0.0377 (10)   0.0306 (10)   0.0074 (9)    −0.0113 (8)   −0.0182 (8)
  C26   0.0341 (10)   0.0368 (10)   0.0293 (10)   −0.0038 (8)   −0.0030 (8)   −0.0169 (8)
  O1    0.0283 (6)    0.0305 (6)    0.0229 (6)    −0.0031 (5)   −0.0023 (5)   −0.0136 (5)
  O2    0.0382 (7)    0.0401 (7)    0.0359 (7)    −0.0036 (6)   −0.0031 (6)   −0.0232 (6)
  O3    0.0304 (7)    0.0333 (7)    0.0250 (6)    −0.0018 (5)   −0.0018 (5)   −0.0142 (5)
  O4    0.0210 (6)    0.0302 (6)    0.0208 (6)    −0.0024 (5)   0.0024 (5)    −0.0118 (5)
  O5    0.0252 (7)    0.0418 (7)    0.0267 (7)    −0.0050 (5)   0.0036 (5)    −0.0158 (6)
  O6    0.0242 (6)    0.0336 (7)    0.0238 (6)    −0.0030 (5)   0.0018 (5)    −0.0158 (5)
  ----- ------------- ------------- ------------- ------------- ------------- -------------

Geometric parameters (Å, º) {#tablewrapgeomlong}
===========================

  ----------------------- -------------- ----------------------- --------------
  C1---O2                 1.214 (2)      C14---O5                1.214 (2)
  C1---O1                 1.391 (2)      C14---O4                1.3916 (19)
  C1---C2                 1.437 (2)      C14---C15               1.440 (2)
  C2---C3                 1.353 (3)      C15---C16               1.353 (2)
  C2---H2                 0.9500         C15---H15               0.9500
  C3---C9                 1.447 (2)      C16---C22               1.452 (2)
  C3---C13                1.498 (2)      C16---C26               1.501 (2)
  C4---C5                 1.372 (2)      C17---C18               1.373 (2)
  C4---C9                 1.406 (2)      C17---C22               1.405 (2)
  C4---H4                 0.9500         C17---H17               0.9500
  C5---C6                 1.399 (2)      C18---C19               1.402 (2)
  C5---H5                 0.9500         C18---H18               0.9500
  C6---O3                 1.365 (2)      C19---O6                1.3685 (19)
  C6---C7                 1.390 (2)      C19---C20               1.382 (2)
  C7---C8                 1.389 (2)      C20---C21               1.394 (2)
  C7---H7                 0.9500         C20---H20               0.9500
  C8---O1                 1.385 (2)      C21---O4                1.3769 (19)
  C8---C9                 1.394 (2)      C21---C22               1.392 (2)
  C10---O3                1.438 (2)      C23---O6                1.442 (2)
  C10---C11               1.510 (2)      C23---C24               1.513 (2)
  C10---H10A              0.9900         C23---H23A              0.9900
  C10---H10B              0.9900         C23---H23B              0.9900
  C11---C12               1.523 (3)      C24---C25               1.524 (3)
  C11---H11A              0.9900         C24---H24A              0.9900
  C11---H11B              0.9900         C24---H24B              0.9900
  C12---H12A              0.9800         C25---H25A              0.9800
  C12---H12B              0.9800         C25---H25B              0.9800
  C12---H12C              0.9800         C25---H25C              0.9800
  C13---H13A              0.9800         C26---H26A              0.9800
  C13---H13B              0.9800         C26---H26B              0.9800
  C13---H13C              0.9800         C26---H26C              0.9800
                                                                 
  O2---C1---O1            116.67 (16)    O4---C14---C15          117.51 (14)
  O2---C1---C2            126.41 (16)    C16---C15---C14         122.54 (15)
  O1---C1---C2            116.92 (15)    C16---C15---H15         118.7
  C3---C2---C1            122.82 (16)    C14---C15---H15         118.7
  C3---C2---H2            118.6          C15---C16---C22         118.65 (16)
  C1---C2---H2            118.6          C15---C16---C26         121.73 (15)
  C2---C3---C9            119.15 (16)    C22---C16---C26         119.61 (15)
  C2---C3---C13           120.81 (16)    C18---C17---C22         121.56 (16)
  C9---C3---C13           120.03 (16)    C18---C17---H17         119.2
  C5---C4---C9            121.63 (16)    C22---C17---H17         119.2
  C5---C4---H4            119.2          C17---C18---C19         119.83 (15)
  C9---C4---H4            119.2          C17---C18---H18         120.1
  C4---C5---C6            119.99 (16)    C19---C18---H18         120.1
  C4---C5---H5            120.0          O6---C19---C20          123.65 (15)
  C6---C5---H5            120.0          O6---C19---C18          115.75 (14)
  O3---C6---C7            124.58 (16)    C20---C19---C18         120.60 (15)
  O3---C6---C5            115.22 (15)    C19---C20---C21         118.08 (16)
  C7---C6---C5            120.20 (16)    C19---C20---H20         121.0
  C8---C7---C6            118.48 (16)    C21---C20---H20         121.0
  C8---C7---H7            120.8          O4---C21---C22          121.81 (14)
  C6---C7---H7            120.8          O4---C21---C20          115.06 (15)
  O1---C8---C7            115.64 (15)    C22---C21---C20         123.13 (15)
  O1---C8---C9            121.49 (15)    C21---C22---C17         116.77 (15)
  C7---C8---C9            122.87 (16)    C21---C22---C16         118.50 (15)
  C8---C9---C4            116.82 (16)    C17---C22---C16         124.73 (15)
  C8---C9---C3            118.18 (15)    O6---C23---C24          108.36 (13)
  C4---C9---C3            125.00 (16)    O6---C23---H23A         110.0
  O3---C10---C11          107.78 (14)    C24---C23---H23A        110.0
  O3---C10---H10A         110.2          O6---C23---H23B         110.0
  C11---C10---H10A        110.2          C24---C23---H23B        110.0
  O3---C10---H10B         110.2          H23A---C23---H23B       108.4
  C11---C10---H10B        110.2          C23---C24---C25         110.15 (15)
  H10A---C10---H10B       108.5          C23---C24---H24A        109.6
  C10---C11---C12         110.13 (15)    C25---C24---H24A        109.6
  C10---C11---H11A        109.6          C23---C24---H24B        109.6
  C12---C11---H11A        109.6          C25---C24---H24B        109.6
  C10---C11---H11B        109.6          H24A---C24---H24B       108.1
  C12---C11---H11B        109.6          C24---C25---H25A        109.5
  H11A---C11---H11B       108.1          C24---C25---H25B        109.5
  C11---C12---H12A        109.5          H25A---C25---H25B       109.5
  C11---C12---H12B        109.5          C24---C25---H25C        109.5
  H12A---C12---H12B       109.5          H25A---C25---H25C       109.5
  C11---C12---H12C        109.5          H25B---C25---H25C       109.5
  H12A---C12---H12C       109.5          C16---C26---H26A        109.5
  H12B---C12---H12C       109.5          C16---C26---H26B        109.5
  C3---C13---H13A         109.5          H26A---C26---H26B       109.5
  C3---C13---H13B         109.5          C16---C26---H26C        109.5
  H13A---C13---H13B       109.5          H26A---C26---H26C       109.5
  C3---C13---H13C         109.5          H26B---C26---H26C       109.5
  H13A---C13---H13C       109.5          C8---O1---C1            121.32 (13)
  H13B---C13---H13C       109.5          C6---O3---C10           117.68 (13)
  O5---C14---O4           115.87 (15)    C21---O4---C14          120.86 (13)
  O5---C14---C15          126.62 (15)    C19---O6---C23          117.62 (13)
                                                                 
  O2---C1---C2---C3       176.86 (18)    O6---C19---C20---C21    −179.18 (14)
  O1---C1---C2---C3       −3.6 (3)       C18---C19---C20---C21   0.7 (2)
  C1---C2---C3---C9       1.0 (3)        C19---C20---C21---O4    −179.80 (14)
  C1---C2---C3---C13      −179.20 (16)   C19---C20---C21---C22   0.6 (3)
  C9---C4---C5---C6       0.2 (3)        O4---C21---C22---C17    178.73 (14)
  C4---C5---C6---O3       179.21 (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---C16   177.96 (15)
  C5---C6---C7---C8       0.3 (2)        C18---C17---C22---C21   1.5 (2)
  C6---C7---C8---O1       −179.66 (14)   C18---C17---C22---C16   −178.13 (16)
  C6---C7---C8---C9       0.5 (3)        C15---C16---C22---C21   1.9 (2)
  O1---C8---C9---C4       179.26 (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---C17   2.6 (3)
  C7---C8---C9---C3       178.37 (15)    O6---C23---C24---C25    −179.12 (14)
  C5---C4---C9---C8       0.5 (2)        C7---C8---O1---C1       178.93 (14)
  C5---C4---C9---C3       −178.70 (16)   C9---C8---O1---C1       −1.2 (2)
  C2---C3---C9---C8       1.5 (2)        O2---C1---O1---C8       −176.75 (15)
  C13---C3---C9---C8      −178.27 (16)   C2---C1---O1---C8       3.6 (2)
  C2---C3---C9---C4       −179.23 (16)   C7---C6---O3---C10      2.9 (2)
  C13---C3---C9---C4      1.0 (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---C16    177.33 (17)    C22---C21---O4---C14    −1.3 (2)
  O4---C14---C15---C16    −3.4 (2)       C20---C21---O4---C14    179.11 (14)
  C14---C15---C16---C22   0.6 (3)        O5---C14---O4---C21     −176.94 (14)
  C14---C15---C16---C26   179.60 (16)    C15---C14---O4---C21    3.7 (2)
  C22---C17---C18---C19   −0.3 (3)       C20---C19---O6---C23    1.4 (2)
  C17---C18---C19---O6    179.01 (14)    C18---C19---O6---C23    −178.55 (14)
  C17---C18---C19---C20   −0.9 (3)       C24---C23---O6---C19    179.83 (13)
  ----------------------- -------------- ----------------------- --------------

Hydrogen-bond geometry (Å, º) {#tablewraphbondslong}
=============================

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···O5^i^            0.95      2.57      3.296 (2)    133
  C15---H15···O5^ii^         0.95      2.49      3.422 (2)    165
  C18---H18···O6^iii^        0.95      2.45      3.402 (2)    175
  C11---H11*A*···*Cg*2^iv^   0.99      2.76      3.6087 (4)   140
  C24---H24*A*···*Cg*4^v^    0.99      2.81      3.613 (2)    139
  C23---H23*B*···*Cg*3^v^    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.

![The mol­ecular structure of (I)[](#scheme1){ref-type="chem"}, 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 *Cg*1 (C4---C9) and *Cg2* (C17---C22).](e-70-00451-fig1){#fig1}

![View of the supra­molecular tape structure along \[100\] sustained by C---H⋯O hydrogen bonds (dashed lines).](e-70-00451-fig2){#fig2}

![View of the C---H⋯π hydrogen bonds (dashed lines) between neighbouring tapes. *Cg*2′, *Cg*3′ \[symmetry code: (′) −*x* + 1, −*y* + 2, −*z*\] and *Cg*4′ \[symmetry code: (′) −*x* + 1, −*y* + 1, −*z* + 1\].](e-70-00451-fig3){#fig3}

###### Hydrogen-bond geometry (, )

*Cg*2, *Cg*3 and *Cg*4 are the centroids of the O1/C1C3/C8/C9, C17C22 and O4/C14C16/C21/C22 rings, respectively.

  *D*H*A*               *D*H   H*A*   *D* *A*     *D*H*A*
  --------------------- ------ ------ ----------- ---------
  C5H5O5^i^             0.95   2.57   3.296(2)    133
  C15H15O5^ii^          0.95   2.49   3.422(2)    165
  C18H18O6^iii^         0.95   2.45   3.402(2)    175
  C11H11*A* *Cg*2^iv^   0.99   2.76   3.6087(4)   140
  C24H24*A* *Cg*4^v^    0.99   2.81   3.613(2)    139
  C23H23*B* *Cg*3^v^    0.99   2.75   3.614(2)    145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

###### Experimental details

  ------------------------------------------------------------------------- ----------------------------------------------
  Crystal data                                                              
  Chemical formula                                                          C~13~H~14~O~3~
  *M* ~r~                                                                   218.24
  Crystal system, space group                                               Triclinic, *P*
  Temperature (K)                                                           100
  *a*, *b*, *c* ()                                                          7.2418(9), 11.5459(14), 14.5301(17)
  , , ()                                                                    69.014(2), 76.086(2), 84.124(2)
  *V* (^3^)                                                                 1100.9(2)
  *Z*                                                                       4
  Radiation type                                                            Mo *K*
  (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[@bb6])
  *T* ~min~, *T* ~max~                                                      0.977, 0.981
  No. of measured, independent and observed \[*I* \> 2(*I*)\] reflections   9469, 3872, 3420
  *R* ~int~                                                                 0.030
  (sin /)~max~ (^1^)                                                        0.595
                                                                            
  Refinement                                                                
  *R*\[*F* ^2^ \> 2(*F* ^2^)\], *wR*(*F* ^2^), *S*                          0.047, 0.122, 1.12
  No. of reflections                                                        3872
  No. of parameters                                                         293
  H-atom treatment                                                          H-atom parameters constrained
  ~max~, ~min~ (e ^3^)                                                      0.22, 0.25
  ------------------------------------------------------------------------- ----------------------------------------------

Computer programs: *SMART* (Bruker, 2000[@bb2]), *SAINT-Plus* (Bruker, 2001[@bb3]), *DIAMOND* (Brandenburg, 1997[@bb1]), *SHELXTL-NT* (Sheldrick, 2008[@bb7]) and *publCIF* (Westrip, 2010[@bb9]).
