Methyl 3′,4′,5′-trimeth­oxy­biphenyl-4-carboxyl­ate

Lahtinen, M.; Nättinen, K.; Nummelin, S.

doi:10.1107/S1600536813004133

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o383

doi:10.1107/S1600536813004133

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Methyl 3′,4′,5′-trimethoxybiphenyl-4-carboxylate

Manu Lahtinen,^a Kalle Nättinen ^b and Sami Nummelin ^c ^*

^aUniversity of Jyväskylä, Department of Chemistry, PO Box 35, FI-40014 JY, Finland, ^bVTT Technical Research Centre of Finland, Tampere, FIN-33101, Finland, and ^cMolecular Materials, Department of Applied Physics, School of Science, Aalto University, PO Box 15100, FI-00076 Aalto, Finland
^*Correspondence e-mail: sami.nummelin@aalto.fi

(Received 22 January 2013; accepted 11 February 2013; online 16 February 2013)

In the title compound, C₁₇H₁₈O₅, the dihedral angle between the benzene rings is 31.23 (16)°. In the crystal, the molecules are packed in an antiparallel fashion in layers along the a axis. In each layer, very weak C—H⋯O hydrogen bonds occur between the methoxy and methyl ester groups. Weak C—H⋯π interactions between the 4′- and 5′-methoxy groups and neighbouring benzene rings [methoxy-C–ring centroid distances = 4.075 and 3.486 Å, respectively] connect the layers.

Related literature

For a related structure, see: Li et al. (2012 ). For the nature of hydrogen bonding, see Steiner (2002 ); For related biphenyl structures, see: Leowanawat et al. (2011 ); Wilson et al. (2008 ); Percec et al. (2004 ); Suzuki (1999 ). For details of the synthesis and amphiphilic supramolecular biphenyl dendrimers, see: Percec et al. (2006 , 2007 ). For general background to self-assembling dendrons and dendrimers, see: Rosen et al. (2009 ); For the use of aromatic and aliphatic ester derivatives in the synthesis of dendrimers and dendrons, see Nummelin et al. (2000 ); Twibanire & Grindley (2012 ).

Experimental

Crystal data

C₁₇H₁₈O₅
M_r = 302.31
Triclinic, $[P \overline 1]$
a = 7.9103 (5) Å
b = 8.6054 (7) Å
c = 11.8779 (7) Å
α = 92.834 (6)°
β = 92.448 (5)°
γ = 115.822 (7)°
V = 725.07 (9) Å³
Z = 2
Cu Kα radiation
μ = 0.84 mm⁻¹
T = 123 K
0.49 × 0.23 × 0.10 mm

Data collection

Agilent SuperNova (Dual source with Cu, Atlas) diffractometer
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010) T_min = 0.827, T_max = 0.951
4547 measured reflections
2731 independent reflections
2524 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.096
S = 1.05
2731 reflections
204 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2ⁱ	0.98	2.58	3.4933 (15)	156
C18—H18C⋯O14ⁱⁱ	0.98	2.50	3.4453 (16)	161
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813004133/fj2614sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004133/fj2614Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004133/fj2614Isup3.cml

checkCIF report

Comment top

Aromatic and aliphatic ester derivatives are extensively used for the synthesis of various types of dendrimers and dendrons (Nummelin et al. 2000, Twibanire et al. 2012). In addition to arylmethyl ether-ester compounds, corresponding biphenyls are employed as building blocks for the construction of amphiphilic dendrons (Percec et al. 2006, 2007). These dendrons self-assemble into hollow and non-hollow supramolecular dendrimers that further self-organize into periodic assemblies (Rosen et al. 2009). The key step in the multi-step reaction sequence is a metal catalyzed aryl-aryl cross-coupling (Percec et al. 2004, 2006; Suzuki 1999). As a contribution to a structural study of biphenyl ether derivatives we report here the title compound methyl-(3',4',5'-trimethoxybiphenyl)-4-carboxylate (I).

Compound (I) crystallizes in triclinic space group P-1 (No. 2) without any solvent molecule in an asymmetric unit (Fig. 1). The intramolecular dihedral angle between the phenyl moieties is 31.23 (16)° [C7–C8–C11–C12]. The molecules are packed in antiparaller rows along a-axis (Fig. 2). On each layer of molecules, very weak C–H···O hydrogen bonds (Steiner 2002) are found between the methoxy and methyl ester groups d(H···A) varying from 2.5 to 2.6 Å (Fig. 3). The 4'-methoxy groups are pointing out from the otherwise planar molecules with bond and torsion angles of 121.07 (10)° and -72.99 (13)° [C13–C16–O17; C13–C16–O17–C18], respectively. In consequence of the projecting methoxy group and the 5'-methoxy group, the molecule layers are interconnected (Fig. 4.) via C–H···π interactions occurring between methoxy group H atoms and close by phenyl rings with distances of 4.075 and 3.846 Å [from methoxy(C) to phenyl ring centroid].

Related literature top

For a related structure, see: Li et al. (2012). For the nature of hydrogen bonding, see Steiner (2002); For related biphenyl structures, see: Leowanawat et al. (2011); Wilson et al. (2008); Percec et al. (2004); For details of the synthesis and amphiphilic supramolecular biphenyl dendrimers, see: Percec et al. (2006, 2007); ; Suzuki (1999). For general background to self-assembling dendrons and dendrimers, see: Rosen et al. (2009); For the use of aromatic and aliphatic ester derivatives in the synthesis of dendrimers and dendrons, see Nummelin et al. (2000); Twibanire & Grindley (2012).

Experimental top

3',4',5'-trimethoxy-biphenyl-4-carboxylic acid (21.0 g, 72.8 mmol) was dissolved in MeOH (300 ml) and conc. sulfuric acid (3 ml). The solution was stirred under reflux for 14 h and then allowed to cool down to ambient temperature. The precipitate was collected by filtration, washed with water and dried in vacuo affording the title ester (20.4 g, 93%) as a white crystalline solid. Crystals suitable for a single-crystal structure determination were obtained from a slow evaporation of ethanol solution.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The asymmetric unit of (I) showing labeling scheme and displacement ellipsoids with 50% probability.
	Fig. 2. Molecular packing along a-axis. Hydrogen atoms are omitted for clarity.
	Fig. 3. View of C–H···O contact network on a single molecule layer.
	Fig. 4. View along (1 - 2 2) plane showing weak C–H···π interactions between the layers of molecules.

Methyl 3',4',5'-trimethoxybiphenyl-4-carboxylate top

Crystal data top

C₁₇H₁₈O₅	Z = 2
M_r = 302.31	F(000) = 320
Triclinic, P1	D_x = 1.385 Mg m⁻³
a = 7.9103 (5) Å	Cu Kα radiation, λ = 1.5418 Å
b = 8.6054 (7) Å	Cell parameters from 3244 reflections
c = 11.8779 (7) Å	θ = 3.7–76.2°
α = 92.834 (6)°	µ = 0.84 mm⁻¹
β = 92.448 (5)°	T = 123 K
γ = 115.822 (7)°	Plate, colourless
V = 725.07 (9) Å³	0.49 × 0.23 × 0.10 mm

Data collection top

Agilent SuperNova (Dual source with Cu, Atlas) diffractometer	2731 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2524 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.016
Detector resolution: 10.3953 pixels mm^-1	θ_max = 70.0°, θ_min = 3.7°
ω scans	h = −6→9
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	k = −10→10
T_min = 0.827, T_max = 0.951	l = −14→14
4547 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0554P)² + 0.167P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2731 reflections	Δρ_max = 0.26 e Å⁻³
204 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (13)

Crystal data top

C₁₇H₁₈O₅	γ = 115.822 (7)°
M_r = 302.31	V = 725.07 (9) Å³
Triclinic, P1	Z = 2
a = 7.9103 (5) Å	Cu Kα radiation
b = 8.6054 (7) Å	µ = 0.84 mm⁻¹
c = 11.8779 (7) Å	T = 123 K
α = 92.834 (6)°	0.49 × 0.23 × 0.10 mm
β = 92.448 (5)°

Data collection top

Agilent SuperNova (Dual source with Cu, Atlas) diffractometer	2731 independent reflections
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	2524 reflections with I > 2σ(I)
T_min = 0.827, T_max = 0.951	R_int = 0.016
4547 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.05	Δρ_max = 0.26 e Å⁻³
2731 reflections	Δρ_min = −0.25 e Å⁻³
204 parameters

Special details top

Experimental. (CrysAlisPro; Agilent 2010)

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

	x	y	z	U_iso*/U_eq
O20	0.15945 (10)	0.37481 (10)	0.32775 (6)	0.0189 (2)
O17	0.09397 (11)	0.16999 (10)	0.13913 (7)	0.0215 (2)
O2	1.52912 (10)	1.04374 (10)	0.31139 (7)	0.0209 (2)
O14	0.37423 (11)	0.19633 (11)	0.00966 (7)	0.0228 (2)
O4	1.43214 (11)	1.16372 (11)	0.45157 (7)	0.0249 (2)
C19	0.31151 (15)	0.40188 (14)	0.26702 (9)	0.0164 (2)
C22	0.49386 (15)	0.52658 (14)	0.29919 (9)	0.0164 (2)
H22	0.5177	0.6002	0.3661	0.020*
C16	0.27386 (15)	0.29495 (14)	0.16769 (9)	0.0174 (2)
C6	1.17401 (15)	0.76841 (15)	0.27483 (9)	0.0185 (2)
H6	1.2780	0.7473	0.2559	0.022*
C7	0.99186 (15)	0.64548 (14)	0.24261 (9)	0.0183 (2)
H7	0.9724	0.5398	0.2030	0.022*
C11	0.64163 (15)	0.54313 (14)	0.23285 (9)	0.0166 (2)
C10	1.05099 (15)	0.95224 (14)	0.36160 (9)	0.0191 (2)
H10	1.0707	1.0566	0.4032	0.023*
C5	1.20468 (15)	0.92276 (14)	0.33487 (9)	0.0168 (2)
C8	0.83642 (15)	0.67484 (14)	0.26762 (9)	0.0164 (2)
C18	0.00490 (16)	0.20396 (16)	0.04195 (11)	0.0254 (3)
H18A	0.0834	0.2196	−0.0221	0.038*
H18B	−0.0109	0.3094	0.0586	0.038*
H18C	−0.1187	0.1061	0.0230	0.038*
C9	0.86947 (15)	0.83046 (14)	0.32792 (10)	0.0190 (2)
H9	0.7660	0.8529	0.3460	0.023*
C3	1.39732 (15)	1.05633 (14)	0.37365 (9)	0.0180 (2)
C13	0.42300 (16)	0.31014 (14)	0.10261 (9)	0.0183 (2)
C15	0.51955 (16)	0.20895 (16)	−0.06177 (10)	0.0235 (3)
H15A	0.4656	0.1228	−0.1263	0.035*
H15B	0.6151	0.1876	−0.0190	0.035*
H15C	0.5778	0.3252	−0.0890	0.035*
C12	0.60543 (15)	0.43431 (14)	0.13456 (9)	0.0181 (2)
H12	0.7057	0.4451	0.0894	0.022*
C21	0.19948 (16)	0.44995 (16)	0.44155 (9)	0.0225 (3)
H21A	0.2520	0.5762	0.4413	0.034*
H21B	0.2908	0.4186	0.4804	0.034*
H21C	0.0831	0.4065	0.4809	0.034*
C1	1.72008 (15)	1.17042 (15)	0.34262 (11)	0.0229 (3)
H1A	1.8043	1.1574	0.2888	0.034*
H1B	1.7580	1.1529	0.4188	0.034*
H1C	1.7275	1.2870	0.3415	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O20	0.0124 (4)	0.0220 (4)	0.0179 (4)	0.0041 (3)	0.0012 (3)	−0.0038 (3)
O17	0.0139 (4)	0.0212 (4)	0.0202 (4)	−0.0003 (3)	−0.0014 (3)	−0.0019 (3)
O2	0.0114 (4)	0.0209 (4)	0.0239 (4)	0.0017 (3)	0.0009 (3)	−0.0050 (3)
O14	0.0173 (4)	0.0238 (4)	0.0196 (4)	0.0029 (3)	0.0015 (3)	−0.0086 (3)
O4	0.0183 (4)	0.0222 (4)	0.0269 (4)	0.0034 (3)	−0.0004 (3)	−0.0090 (3)
C19	0.0137 (5)	0.0174 (5)	0.0174 (5)	0.0061 (4)	0.0014 (4)	0.0017 (4)
C22	0.0148 (5)	0.0159 (5)	0.0158 (5)	0.0048 (4)	−0.0011 (4)	−0.0018 (4)
C16	0.0125 (5)	0.0158 (5)	0.0185 (5)	0.0016 (4)	−0.0017 (4)	−0.0010 (4)
C6	0.0139 (5)	0.0210 (5)	0.0191 (5)	0.0067 (4)	0.0015 (4)	−0.0018 (4)
C7	0.0160 (5)	0.0177 (5)	0.0180 (5)	0.0052 (4)	0.0000 (4)	−0.0045 (4)
C11	0.0141 (5)	0.0157 (5)	0.0179 (5)	0.0048 (4)	−0.0008 (4)	0.0007 (4)
C10	0.0173 (5)	0.0162 (5)	0.0211 (5)	0.0052 (4)	0.0023 (4)	−0.0022 (4)
C5	0.0141 (5)	0.0174 (5)	0.0150 (5)	0.0035 (4)	0.0004 (4)	0.0004 (4)
C8	0.0148 (5)	0.0167 (5)	0.0146 (5)	0.0040 (4)	0.0005 (4)	0.0005 (4)
C18	0.0174 (5)	0.0251 (6)	0.0294 (6)	0.0066 (5)	−0.0066 (5)	−0.0042 (5)
C9	0.0144 (5)	0.0183 (5)	0.0227 (6)	0.0058 (4)	0.0021 (4)	−0.0011 (4)
C3	0.0160 (5)	0.0175 (5)	0.0184 (5)	0.0056 (4)	0.0011 (4)	0.0004 (4)
C13	0.0185 (5)	0.0178 (5)	0.0158 (5)	0.0059 (4)	−0.0006 (4)	−0.0019 (4)
C15	0.0214 (6)	0.0264 (6)	0.0200 (6)	0.0084 (5)	0.0031 (4)	−0.0054 (5)
C12	0.0143 (5)	0.0193 (5)	0.0183 (5)	0.0055 (4)	0.0013 (4)	−0.0006 (4)
C21	0.0173 (5)	0.0282 (6)	0.0176 (6)	0.0063 (5)	0.0027 (4)	−0.0032 (4)
C1	0.0120 (5)	0.0201 (6)	0.0298 (6)	0.0012 (4)	0.0000 (4)	−0.0011 (5)

Geometric parameters (Å, º) top

O20—C19	1.3667 (13)	C10—H10	0.9500
O20—C21	1.4298 (13)	C10—C5	1.3916 (15)
O17—C16	1.3733 (13)	C10—C9	1.3851 (16)
O17—C18	1.4345 (14)	C5—C3	1.4891 (15)
O2—C3	1.3424 (13)	C8—C9	1.3997 (15)
O2—C1	1.4442 (13)	C18—H18A	0.9800
O14—C13	1.3618 (13)	C18—H18B	0.9800
O14—C15	1.4271 (13)	C18—H18C	0.9800
O4—C3	1.2076 (14)	C9—H9	0.9500
C19—C22	1.3937 (15)	C13—C12	1.3921 (15)
C19—C16	1.3969 (15)	C15—H15A	0.9800
C22—H22	0.9500	C15—H15B	0.9800
C22—C11	1.3972 (15)	C15—H15C	0.9800
C16—C13	1.4000 (16)	C12—H12	0.9500
C6—H6	0.9500	C21—H21A	0.9800
C6—C7	1.3881 (15)	C21—H21B	0.9800
C6—C5	1.3937 (15)	C21—H21C	0.9800
C7—H7	0.9500	C1—H1A	0.9800
C7—C8	1.3994 (15)	C1—H1B	0.9800
C11—C8	1.4857 (14)	C1—H1C	0.9800
C11—C12	1.3971 (15)

C19—O20—C21	116.33 (8)	H18A—C18—H18B	109.5
C16—O17—C18	113.77 (9)	H18A—C18—H18C	109.5
C3—O2—C1	115.40 (8)	H18B—C18—H18C	109.5
C13—O14—C15	117.61 (9)	C10—C9—C8	120.93 (10)
O20—C19—C22	123.79 (10)	C10—C9—H9	119.5
O20—C19—C16	115.53 (9)	C8—C9—H9	119.5
C22—C19—C16	120.67 (10)	O2—C3—C5	111.90 (9)
C19—C22—H22	120.1	O4—C3—O2	123.63 (10)
C19—C22—C11	119.89 (10)	O4—C3—C5	124.47 (10)
C11—C22—H22	120.1	O14—C13—C16	115.08 (10)
O17—C16—C19	119.67 (10)	O14—C13—C12	124.58 (10)
O17—C16—C13	121.07 (10)	C12—C13—C16	120.34 (10)
C19—C16—C13	119.14 (10)	O14—C15—H15A	109.5
C7—C6—H6	119.9	O14—C15—H15B	109.5
C7—C6—C5	120.16 (10)	O14—C15—H15C	109.5
C5—C6—H6	119.9	H15A—C15—H15B	109.5
C6—C7—H7	119.5	H15A—C15—H15C	109.5
C6—C7—C8	121.03 (10)	H15B—C15—H15C	109.5
C8—C7—H7	119.5	C11—C12—H12	119.9
C22—C11—C8	119.97 (10)	C13—C12—C11	120.23 (10)
C12—C11—C22	119.69 (10)	C13—C12—H12	119.9
C12—C11—C8	120.34 (10)	O20—C21—H21A	109.5
C5—C10—H10	119.8	O20—C21—H21B	109.5
C9—C10—H10	119.8	O20—C21—H21C	109.5
C9—C10—C5	120.44 (10)	H21A—C21—H21B	109.5
C6—C5—C3	122.00 (10)	H21A—C21—H21C	109.5
C10—C5—C6	119.29 (10)	H21B—C21—H21C	109.5
C10—C5—C3	118.69 (10)	O2—C1—H1A	109.5
C7—C8—C11	120.91 (10)	O2—C1—H1B	109.5
C7—C8—C9	118.14 (10)	O2—C1—H1C	109.5
C9—C8—C11	120.95 (10)	H1A—C1—H1B	109.5
O17—C18—H18A	109.5	H1A—C1—H1C	109.5
O17—C18—H18B	109.5	H1B—C1—H1C	109.5
O17—C18—H18C	109.5

O20—C19—C22—C11	178.85 (10)	C7—C6—C5—C10	−0.25 (17)
O20—C19—C16—O17	−1.73 (15)	C7—C6—C5—C3	178.45 (10)
O20—C19—C16—C13	−177.75 (10)	C7—C8—C9—C10	0.19 (17)
O17—C16—C13—O14	1.62 (16)	C11—C8—C9—C10	179.15 (10)
O17—C16—C13—C12	−178.14 (10)	C10—C5—C3—O2	−157.96 (10)
O14—C13—C12—C11	−178.77 (10)	C10—C5—C3—O4	21.96 (17)
C19—C22—C11—C8	−179.40 (9)	C5—C6—C7—C8	1.18 (17)
C19—C22—C11—C12	−0.02 (16)	C5—C10—C9—C8	0.72 (17)
C19—C16—C13—O14	177.58 (10)	C8—C11—C12—C13	179.52 (10)
C19—C16—C13—C12	−2.18 (17)	C18—O17—C16—C19	111.07 (11)
C22—C19—C16—O17	178.33 (9)	C18—O17—C16—C13	−72.99 (13)
C22—C19—C16—C13	2.31 (17)	C9—C10—C5—C6	−0.70 (17)
C22—C11—C8—C7	148.15 (11)	C9—C10—C5—C3	−179.43 (10)
C22—C11—C8—C9	−30.78 (15)	C15—O14—C13—C16	178.23 (10)
C22—C11—C12—C13	0.14 (16)	C15—O14—C13—C12	−2.02 (16)
C16—C19—C22—C11	−1.23 (16)	C12—C11—C8—C7	−31.23 (16)
C16—C13—C12—C11	0.97 (17)	C12—C11—C8—C9	149.84 (11)
C6—C7—C8—C11	179.90 (10)	C21—O20—C19—C22	−15.21 (15)
C6—C7—C8—C9	−1.14 (16)	C21—O20—C19—C16	164.86 (10)
C6—C5—C3—O2	23.34 (15)	C1—O2—C3—O4	−0.72 (16)
C6—C5—C3—O4	−156.74 (12)	C1—O2—C3—C5	179.20 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.98	2.58	3.4933 (15)	156
C18—H18C···O14ⁱⁱ	0.98	2.50	3.4453 (16)	161

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈O₅
M_r	302.31
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	7.9103 (5), 8.6054 (7), 11.8779 (7)
α, β, γ (°)	92.834 (6), 92.448 (5), 115.822 (7)
V (Å³)	725.07 (9)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.49 × 0.23 × 0.10

Data collection
Diffractometer	Agilent SuperNova (Dual source with Cu, Atlas) diffractometer
Absorption correction	Analytical (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.827, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	4547, 2731, 2524
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.096, 1.05
No. of reflections	2731
No. of parameters	204
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.25

Computer programs: CrysAlis PRO (Agilent, 2010), SUPERFLIP (Palatinus & Chapuis, 2007), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.98	2.58	3.4933 (15)	156
C18—H18C···O14ⁱⁱ	0.98	2.50	3.4453 (16)	161

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x, −y, −z.

Acknowledgements

SN acknowledges the Academy of Finland for financial support (No. 138850).

References

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