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

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

doi:10.1107/S1600536813005333

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o460

doi:10.1107/S1600536813005333

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Methyl 3′,5′-dimethoxybiphenyl-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 12 February 2013; accepted 24 February 2013; online 28 February 2013)

In the title compound, C₁₆H₁₆O₄, the dihedral angle between the benzene rings is 28.9 (2)°. In the crystal, molecules are packed in layers parallel to the b axis in which they are connected via weak intermolecular C—H⋯O contacts. Face-to-face π–π interactions also exist between the benzene rings of adjacent molecules, with centroid–centroid and plane-to-plane shift distances of 3.8597 (14) and 1.843 (2) Å, respectively.

Related literature

For related structures, see: Lahtinen et al. (2013 ); Van Eerdenbrugh et al. (2010 ). For the nature of hydrogen bonding, see: Steiner (2002 ). For synthesis details and related supramolecular structures based on biphenyls, see: Percec et al. (2006 , 2007 ). For related synthetic biphenyl structures, see: Rosen et al. (2008 ); Percec et al. (2004 ); Wolfe et al. (1999 ). For polyester functionalized dendrons and dendrimers, see: Nummelin et al. (2000 ). For a general review on self-assembling dendrons and dendrimers, see: Rosen et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₆O₄
M_r = 272.29
Triclinic, $[P \overline 1]$
a = 6.0990 (9) Å
b = 7.1622 (16) Å
c = 16.2408 (18) Å
α = 96.589 (14)°
β = 91.472 (11)°
γ = 112.493 (18)°
V = 649.27 (19) Å³
Z = 2
Cu Kα radiation
μ = 0.82 mm⁻¹
T = 123 K
0.29 × 0.19 × 0.04 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: analytical CrysAlis PRO; Agilent, 2010 ) T_min = 0.924, T_max = 0.983
3989 measured reflections
2395 independent reflections
2025 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.111
S = 1.05
2395 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.19 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
C6—H6⋯O2ⁱ	0.95	2.89	3.7702 (19)	154
C7—H7⋯O4ⁱⁱ	0.95	2.85	3.4607 (19)	123
C12—H12⋯O4ⁱⁱ	0.95	2.71	3.644 (2)	170
C16—H16⋯O14ⁱⁱⁱ	0.95	2.65	3.514 (2)	151
C1—H1A⋯O4^iv	0.98	2.73	3.665 (2)	159
C19—H19A⋯O18^v	0.98	2.65	3.538 (2)	151
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+2, -z+2; (iii) -x, -y+1, -z+1; (iv) x+1, y, z; (v) -x+1, -y, -z+1.

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/S1600536813005333/fj2616sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813005333/fj2616Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813005333/fj2616Isup3.cml

checkCIF report

Comment top

Biphenyls represent a new class of arylmethyl ethers and esters that serve as building blocks for the construction of amphiphilic dendrons. These dendrons, synthesized in a multi-step reaction sequence, self-assemble into hollow and non-hollow supramolecular dendrimers that further self-organize into periodic assemblies (Percec et al. 2006, 2007). The key synthetic step is the C—C bond formation between the aromatic rings. This is accomplished with metal catalyzed cross-coupling reaction (Percec et al. 2004, 2006; Rosen et al. 2008, Wolfe et al. 1999). As a contribution to a structural study of biphenyl ester derivatives we report here the title compound methyl-(3',5'-dimethoxy-biphenyl)-4-carboxylate (I).

Compound (I) crystallizes in triclinic space group P-1 (No. 2) without any solvent molecules, and having a single molecule in an asymmetric unit (Fig. 1). The intramolecular dihedral angle between the phenyl rings is 28.9 (2)°, similar to that of reported for analogous methyl 3',4',5'-trimethoxybiphenyl-4- carboxylate (Lahtinen et al. 2013). The molecules are packed in antiparallel arrangement (Fig. 2). Weak intermolecular π-π interactions (face-to-face) exist between adjacent aromatic rings having centroid-centroid and plane to plane shift distances of 3.8597 (14) and 1.843 (2) Å, respectively. Whereas weak CH-π interaction occurs between a methoxy group and nearby phenyl ring with a d(D···centroid) of 3.8303 (19) Å. Additionally, weak intermolecular CH···O hydrogen bonds occur between aromatic H atoms and neighboring methoxy O atoms with d(D···A) varying between 3.4607 (19), and 3.7702 (19) Å. Moreover, weak hydrogen bond exist between the carbonyl oxygen and aromatic ring hydrogen (C12—H12···O4) with d(D···A) of 3.644 (2) Å. The methyl ester and the two methoxy groups show characteristic geometries, typical bond distances and angles for these groups (see Tables) and are in planar orientation towards their host rings.

Related literature top

For related structures, see: Lahtinen et al. (2013); Van Eerdenbrugh et al. (2010). For the nature of hydrogen bonding, see: Steiner (2002). For synthesis details and related supramolecular structures based on biphenyls, see: Percec et al. (2006, 2007). For related synthetic biphenyl structures, see: Rosen et al. (2008); Percec et al. (2004); Wolfe et al. (1999). For polyester functionalized dendrons and dendrimers, see: Nummelin et al. (2000). For a general review on self-assembling dendrons and dendrimers, see: Rosen et al. (2009) .

Experimental top

3',5'-dimethoxy-biphenyl-4-carboxylic acid (15.50 g, 60.00 mmol) was dissolved in methanol (300 ml) and sulfuric acid (3 ml). The solution was stirred under reflux for 16 h and then allowed to cool down to room temperature. Water (600 ml) was added, the resulting precipitate was collected by suction filtration. The solid was washed with water, dried in vacuo affording the title compound as a white crystalline solid (15.69 g, 96%). Single-crystals were obtained from a slow evaporation of ethanol.

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 molecular structure and labelling of the title compound. The displacement ellipsoids are drawn with 50% probability.
	Fig. 2. Packing scheme along a-axis.
	Fig. 3. Weak CH···O (blue lines), CH···π and π···π interactions occurring in the structure.

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

Crystal data top

C₁₆H₁₆O₄	Z = 2
M_r = 272.29	F(000) = 288
Triclinic, P1	D_x = 1.393 Mg m⁻³
a = 6.0990 (9) Å	Cu Kα radiation, λ = 1.5418 Å
b = 7.1622 (16) Å	Cell parameters from 2092 reflections
c = 16.2408 (18) Å	θ = 5.5–76.0°
α = 96.589 (14)°	µ = 0.82 mm⁻¹
β = 91.472 (11)°	T = 123 K
γ = 112.493 (18)°	Plate, colourless
V = 649.27 (19) Å³	0.29 × 0.19 × 0.04 mm

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2395 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2025 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.025
Detector resolution: 10.3953 pixels mm^-1	θ_max = 69.0°, θ_min = 5.5°
ω scans	h = −5→7
Absorption correction: analytical CrysAlis PRO; Agilent, 2010)	k = −8→8
T_min = 0.924, T_max = 0.983	l = −19→19
3989 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0591P)² + 0.1033P] where P = (F_o² + 2F_c²)/3
2395 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₆H₁₆O₄	γ = 112.493 (18)°
M_r = 272.29	V = 649.27 (19) Å³
Triclinic, P1	Z = 2
a = 6.0990 (9) Å	Cu Kα radiation
b = 7.1622 (16) Å	µ = 0.82 mm⁻¹
c = 16.2408 (18) Å	T = 123 K
α = 96.589 (14)°	0.29 × 0.19 × 0.04 mm
β = 91.472 (11)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2395 independent reflections
Absorption correction: analytical CrysAlis PRO; Agilent, 2010)	2025 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.983	R_int = 0.025
3989 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
2395 reflections	Δρ_min = −0.25 e Å⁻³
184 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

	x	y	z	U_iso*/U_eq
O4	0.72065 (19)	0.88715 (17)	1.15112 (6)	0.0256 (3)
O2	1.01438 (18)	0.78669 (16)	1.11239 (6)	0.0245 (3)
O18	0.46733 (19)	0.23876 (16)	0.56673 (6)	0.0256 (3)
O14	0.1145 (2)	0.71333 (18)	0.59191 (7)	0.0301 (3)
C3	0.8129 (3)	0.8161 (2)	1.09788 (9)	0.0205 (3)
C6	0.5135 (3)	0.7715 (2)	0.98314 (9)	0.0210 (3)
H6	0.4281	0.8202	1.0223	0.025*
C17	0.4269 (3)	0.3845 (2)	0.61901 (9)	0.0213 (3)
C13	0.2432 (3)	0.6276 (2)	0.63282 (9)	0.0220 (3)
C7	0.4295 (3)	0.7185 (2)	0.89982 (9)	0.0212 (3)
H7	0.2877	0.7335	0.8827	0.025*
C11	0.4573 (2)	0.5869 (2)	0.75182 (9)	0.0201 (3)
C5	0.7225 (3)	0.7530 (2)	1.00911 (9)	0.0202 (3)
C12	0.3244 (3)	0.6839 (2)	0.71684 (9)	0.0214 (3)
H12	0.2899	0.7865	0.7497	0.026*
C16	0.2934 (3)	0.4787 (2)	0.58389 (9)	0.0226 (3)
H16	0.2370	0.4417	0.5269	0.027*
C8	0.5486 (2)	0.6439 (2)	0.84072 (9)	0.0196 (3)
C9	0.7577 (3)	0.6253 (2)	0.86810 (9)	0.0223 (3)
H9	0.8427	0.5753	0.8292	0.027*
C20	0.5067 (3)	0.4362 (2)	0.70285 (9)	0.0211 (3)
H20	0.5948	0.3689	0.7268	0.025*
C10	0.8431 (3)	0.6785 (2)	0.95095 (9)	0.0222 (3)
H10	0.9851	0.6639	0.9682	0.027*
C1	1.1197 (3)	0.8460 (2)	1.19672 (9)	0.0255 (3)
H1A	1.2785	0.8419	1.1987	0.038*
H1B	1.0194	0.7518	1.2325	0.038*
H1C	1.1328	0.9848	1.2163	0.038*
C19	0.6415 (3)	0.1676 (3)	0.59536 (10)	0.0271 (3)
H19A	0.6742	0.0828	0.5495	0.041*
H19B	0.5810	0.0866	0.6406	0.041*
H19C	0.7884	0.2845	0.6156	0.041*
C15	0.0299 (3)	0.8481 (3)	0.64007 (10)	0.0279 (4)
H15A	−0.0638	0.8943	0.6035	0.042*
H15B	0.1656	0.9662	0.6678	0.042*
H15C	−0.0700	0.7764	0.6820	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0290 (6)	0.0305 (6)	0.0189 (5)	0.0141 (5)	0.0027 (4)	−0.0002 (4)
O2	0.0254 (6)	0.0301 (6)	0.0191 (5)	0.0135 (5)	−0.0029 (4)	−0.0018 (4)
O18	0.0309 (6)	0.0269 (6)	0.0208 (5)	0.0150 (5)	−0.0011 (4)	−0.0025 (4)
O14	0.0377 (6)	0.0365 (6)	0.0232 (6)	0.0235 (5)	−0.0032 (5)	0.0010 (5)
C3	0.0208 (7)	0.0181 (7)	0.0214 (7)	0.0059 (6)	0.0011 (6)	0.0039 (6)
C6	0.0231 (7)	0.0198 (7)	0.0201 (7)	0.0084 (6)	0.0038 (6)	0.0012 (6)
C17	0.0219 (7)	0.0198 (7)	0.0201 (7)	0.0064 (6)	0.0033 (6)	0.0008 (6)
C13	0.0217 (7)	0.0231 (8)	0.0218 (7)	0.0087 (6)	0.0004 (6)	0.0051 (6)
C7	0.0213 (7)	0.0232 (8)	0.0199 (7)	0.0094 (6)	0.0013 (6)	0.0036 (6)
C11	0.0181 (7)	0.0202 (7)	0.0194 (7)	0.0044 (6)	0.0026 (6)	0.0034 (6)
C5	0.0221 (7)	0.0182 (7)	0.0187 (7)	0.0060 (6)	0.0019 (6)	0.0029 (5)
C12	0.0211 (7)	0.0221 (8)	0.0202 (7)	0.0079 (6)	0.0013 (6)	0.0015 (6)
C16	0.0246 (8)	0.0237 (8)	0.0180 (7)	0.0081 (6)	0.0006 (6)	0.0017 (6)
C8	0.0202 (7)	0.0169 (7)	0.0199 (7)	0.0050 (6)	0.0021 (6)	0.0029 (5)
C9	0.0223 (7)	0.0254 (8)	0.0192 (7)	0.0099 (6)	0.0033 (6)	0.0006 (6)
C20	0.0208 (7)	0.0211 (7)	0.0210 (7)	0.0077 (6)	0.0007 (6)	0.0031 (6)
C10	0.0195 (7)	0.0242 (8)	0.0229 (8)	0.0091 (6)	0.0011 (6)	0.0019 (6)
C1	0.0276 (8)	0.0288 (8)	0.0190 (7)	0.0107 (7)	−0.0046 (6)	0.0008 (6)
C19	0.0272 (8)	0.0302 (8)	0.0258 (8)	0.0147 (7)	0.0010 (6)	−0.0017 (6)
C15	0.0299 (8)	0.0294 (8)	0.0284 (8)	0.0164 (7)	0.0004 (6)	0.0021 (6)

Geometric parameters (Å, º) top

O4—C3	1.2107 (18)	C11—C20	1.397 (2)
O2—C3	1.3436 (17)	C5—C10	1.392 (2)
O2—C1	1.4427 (17)	C12—H12	0.9500
O18—C17	1.3694 (17)	C16—H16	0.9500
O18—C19	1.4308 (18)	C8—C9	1.399 (2)
O14—C13	1.3676 (18)	C9—H9	0.9500
O14—C15	1.4278 (18)	C9—C10	1.386 (2)
C3—C5	1.485 (2)	C20—H20	0.9500
C6—H6	0.9500	C10—H10	0.9500
C6—C7	1.391 (2)	C1—H1A	0.9800
C6—C5	1.391 (2)	C1—H1B	0.9800
C17—C16	1.389 (2)	C1—H1C	0.9800
C17—C20	1.393 (2)	C19—H19A	0.9800
C13—C12	1.399 (2)	C19—H19B	0.9800
C13—C16	1.389 (2)	C19—H19C	0.9800
C7—H7	0.9500	C15—H15A	0.9800
C7—C8	1.396 (2)	C15—H15B	0.9800
C11—C12	1.400 (2)	C15—H15C	0.9800
C11—C8	1.487 (2)

C3—O2—C1	115.97 (11)	C7—C8—C11	121.35 (13)
C17—O18—C19	117.27 (11)	C7—C8—C9	117.57 (13)
C13—O14—C15	117.93 (12)	C9—C8—C11	121.09 (13)
O4—C3—O2	123.42 (13)	C8—C9—H9	119.4
O4—C3—C5	125.19 (13)	C10—C9—C8	121.19 (13)
O2—C3—C5	111.38 (12)	C10—C9—H9	119.4
C7—C6—H6	120.0	C17—C20—C11	120.10 (13)
C5—C6—H6	120.0	C17—C20—H20	119.9
C5—C6—C7	119.98 (13)	C11—C20—H20	119.9
O18—C17—C16	115.76 (13)	C5—C10—H10	119.7
O18—C17—C20	123.83 (13)	C9—C10—C5	120.53 (14)
C16—C17—C20	120.40 (13)	C9—C10—H10	119.7
O14—C13—C12	124.10 (13)	O2—C1—H1A	109.5
O14—C13—C16	114.75 (13)	O2—C1—H1B	109.5
C16—C13—C12	121.14 (13)	O2—C1—H1C	109.5
C6—C7—H7	119.2	H1A—C1—H1B	109.5
C6—C7—C8	121.62 (13)	H1A—C1—H1C	109.5
C8—C7—H7	119.2	H1B—C1—H1C	109.5
C12—C11—C8	120.57 (13)	O18—C19—H19A	109.5
C20—C11—C12	119.93 (14)	O18—C19—H19B	109.5
C20—C11—C8	119.50 (13)	O18—C19—H19C	109.5
C6—C5—C3	119.12 (13)	H19A—C19—H19B	109.5
C6—C5—C10	119.11 (14)	H19A—C19—H19C	109.5
C10—C5—C3	121.77 (13)	H19B—C19—H19C	109.5
C13—C12—C11	119.01 (13)	O14—C15—H15A	109.5
C13—C12—H12	120.5	O14—C15—H15B	109.5
C11—C12—H12	120.5	O14—C15—H15C	109.5
C17—C16—C13	119.41 (14)	H15A—C15—H15B	109.5
C17—C16—H16	120.3	H15A—C15—H15C	109.5
C13—C16—H16	120.3	H15B—C15—H15C	109.5

O4—C3—C5—C6	−1.2 (2)	C12—C11—C8—C7	28.9 (2)
O4—C3—C5—C10	177.90 (14)	C12—C11—C8—C9	−150.86 (14)
O2—C3—C5—C6	179.48 (13)	C12—C11—C20—C17	0.9 (2)
O2—C3—C5—C10	−1.4 (2)	C16—C17—C20—C11	−1.4 (2)
O18—C17—C16—C13	179.66 (13)	C16—C13—C12—C11	−0.4 (2)
O18—C17—C20—C11	−179.97 (13)	C8—C11—C12—C13	179.45 (13)
O14—C13—C12—C11	−179.23 (13)	C8—C11—C20—C17	−178.56 (13)
O14—C13—C16—C17	178.85 (13)	C8—C9—C10—C5	−0.3 (2)
C3—C5—C10—C9	−178.42 (14)	C20—C17—C16—C13	1.0 (2)
C6—C7—C8—C11	179.75 (13)	C20—C11—C12—C13	0.0 (2)
C6—C7—C8—C9	−0.4 (2)	C20—C11—C8—C7	−151.58 (14)
C6—C5—C10—C9	0.7 (2)	C20—C11—C8—C9	28.6 (2)
C7—C6—C5—C3	178.20 (13)	C1—O2—C3—O4	−0.2 (2)
C7—C6—C5—C10	−0.9 (2)	C1—O2—C3—C5	179.10 (12)
C7—C8—C9—C10	0.2 (2)	C19—O18—C17—C16	167.89 (13)
C11—C8—C9—C10	179.99 (13)	C19—O18—C17—C20	−13.5 (2)
C5—C6—C7—C8	0.8 (2)	C15—O14—C13—C12	−9.0 (2)
C12—C13—C16—C17	−0.1 (2)	C15—O14—C13—C16	172.12 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.95	2.89	3.7702 (19)	154
C7—H7···O4ⁱⁱ	0.95	2.85	3.4607 (19)	123
C12—H12···O4ⁱⁱ	0.95	2.71	3.644 (2)	170
C16—H16···O14ⁱⁱⁱ	0.95	2.65	3.514 (2)	151
C1—H1A···O4^iv	0.98	2.73	3.665 (2)	159
C19—H19A···O18^v	0.98	2.65	3.538 (2)	151

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆O₄
M_r	272.29
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	6.0990 (9), 7.1622 (16), 16.2408 (18)
α, β, γ (°)	96.589 (14), 91.472 (11), 112.493 (18)
V (Å³)	649.27 (19)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.29 × 0.19 × 0.04

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction	Analytical CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.924, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	3989, 2395, 2025
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.111, 1.05
No. of reflections	2395
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −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
C6—H6···O2ⁱ	0.95	2.89	3.7702 (19)	154
C7—H7···O4ⁱⁱ	0.95	2.85	3.4607 (19)	123
C12—H12···O4ⁱⁱ	0.95	2.71	3.644 (2)	170
C16—H16···O14ⁱⁱⁱ	0.95	2.65	3.514 (2)	151
C1—H1A···O4^iv	0.98	2.73	3.665 (2)	159
C19—H19A···O18^v	0.98	2.65	3.538 (2)	151

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

Acknowledgements

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

References

Agilent (2010). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Lahtinen, M., Nättinen, K. & Nummelin, S. (2013). Acta Cryst. E69, o383. CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nummelin, S., Skrifvars, M. & Rissanen, K. (2000). Top. Curr. Chem. 210, 1–67. CrossRef CAS Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Percec, V., Golding, G. M., Smidrkal, J. & Weichold, O. (2004). J. Org. Chem. 69, 3447–3452. Web of Science CrossRef PubMed CAS Google Scholar
Percec, V., Holerca, M. N., Nummelin, S., Morrison, J. J., Glodde, M., Smidrkal, J., Peterca, M., Uchida, S., Balagurusamy, V. S. K., Sienkowska, M. J. & Heiney, P. A. (2006). Chem. Eur. J. 12, 6216–6241. Web of Science CrossRef PubMed CAS Google Scholar
Percec, V., Smidrkal, J., Peterca, M., Mitchell, C. M., Nummelin, S., Dulcey, A. E., Sienkowska, M. J. & Heiney, P. A. (2007). Chem. Eur. J. 13, 3989–4007. Web of Science CrossRef PubMed CAS Google Scholar
Rosen, B. M., Huang, C. & Percec, V. (2008). Org. Lett. 12, 2597–2600. Web of Science CrossRef Google Scholar
Rosen, B. M., Wilson, C. J., Wilson, D. A., Peterca, M., Imam, M. R. & Percec, V. (2009). Chem. Rev. 109, 6275–6540. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48–76. Web of Science CrossRef CAS Google Scholar
Van Eerdenbrugh, B., Fanwick, P. E. & Taylor, L. S. (2010). Acta Cryst. E66, o2609. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wolfe, J. P., Singer, R. A., Yang, B. H. & Buchwald, S. L. (1999). J. Am. Chem. Soc. 121, 9550–9561. Web of Science CrossRef CAS Google Scholar