6-[(4′-Ethoxycarbonyl-[1,1′-biphenyl]-4-yl)oxy]hexanoic acid

López-Velázquez, D.; Mendoza, A.

doi:10.1107/S1600536813025877

organic compounds

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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1588

doi:10.1107/S1600536813025877

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6-[(4′-Ethoxycarbonyl-[1,1′-biphenyl]-4-yl)oxy]hexanoic acid

Delia López-Velázquez ^a and Angel Mendoza ^b ^*

^aFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Puebla, Pue, Mexico, and ^bCentro de Química, ICUAP, Benemérita Universidad Autónoma de Puebla, Puebla, Pue, Mexico
^*Correspondence e-mail: angel.mendoza@correo.buap.mx

(Received 7 September 2013; accepted 19 September 2013; online 25 September 2013)

In the title compound, C₂₁H₂₄O₅, the dihedral angle between the benzene rings is 19.57 (15)°. In the crystal, the molecular arrangement makes up head-to-head centrosymmetric dimers assembled by pairs of O—H⋯O bonds; this arrangement builds a graph-set ring motif of R²₂(8). The dimers are linked into a tape running along the b-axis direction through C—H⋯O interactions. The packing is further consolidated by C—H⋯π interactions, forming layers parallel to (10-2).

CCDC reference: 962005

Related literature

For hydrogen-bonding assemblies, see: Braga et al. (2004 ). For hydrogen-bonding packing modes and applications of hydrogen bonds, see: Jeong et al. (2006 ); Leiserowitz (1976 ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₁H₂₄O₅
M_r = 356.4
Monoclinic, P 2₁ /c
a = 9.111 (2) Å
b = 14.753 (3) Å
c = 14.427 (2) Å
β = 100.785 (14)°
V = 1904.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.5 × 0.5 × 0.4 mm

Data collection

Siemens P4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.891, T_max = 0.911
4265 measured reflections
3217 independent reflections
1628 reflections with I > 2σ(I)
R_int = 0.031
3 standard reflections every 97 reflections intensity decay: 6%

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.171
S = 1.06
3217 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.80	2.612 (3)	170
C18—H18⋯O1ⁱⁱ	0.93	2.54	3.460 (4)	173
C6—H6A⋯Cg1ⁱⁱⁱ	0.97	2.78	3.668 (4)	152
Symmetry codes: (i) -x+2, -y-2, -z+1; (ii) x, y+1, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: XSCANS (Siemens, 1994 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 962005

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813025877/is5302sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813025877/is5302Isup2.hkl

checkCIF report

Comment top

Hydrogen bonds are the strongest of the non-covalent interactions and have a high degree of directionality. Therefore, the design of molecules with hydrogen bonding capabilities is very important due to its numerous potential application (Braga et al., 2004) in nanotechnology, in crystal engineering, in template synthesis of polymers and networks, as well as in templated processes in biology such as the replication and transcription of nucleic acids. It has long been known that monocarboxylic acid may be interlinked to form the cyclic hydrogen-bonded dimer. This kind of molecular dimer, is well known as supramolecular synthon in crystals of carboxylic acids (Jeong et al., 2006; Leiserowitz et al., 1976). It is also important to point out that the title compound I contains a polymerizable end-group. Therefore it is a precursor for polymeric materials.

In the title compound, the ASU shows a molecule with two non-coplanar phenyl rings bonded by C10 and C13, both rings with p-substitution. The dihedral angle between these planes is 19.57 (15)°. On the other hand, C2 to C6 show an aliphatic extended-chain probably due to intermolecular interactions. The crystal packing makes up a head to head dimer assembled by intermolecular O—H···O bonds between the carboxyl groups (Fig. 1). This arrangement builds a graph-set ring R²₂(8) (Etter et al., 1990; Bernstein et al., 1995). Two more interactions C—H···O and C—H···π interactions, are identified, which stabilize the crystal packing. A tape of molecules from the C18—H18···O1 interaction is formed along the b axis. The C6—H6A···Cg1 interaction is building a layer of molecules parallel to (1 0 2). (Table 1; Cg1 is the centroid of the ring composed of C13–C18.)

Related literature top

For hydrogen-bonding assemblies, see: Braga et al. (2004). For hydrogen-bonding packing modes and applications of hydrogen bonds, see: Jeong et al. (2006); Leiserowitz (1976). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

6.2 g (14 mmol) of benzyl 6-(ethyl 4'-oxydiphenyl-4-carboxylate)-hexanoate was added to 90 ml of dry ethyl acetate. 5% Pd—C (0.029 g) was then added with stirring. The hydrogenolisis was allowed to proceed for 8.5 h under hydrogen atmosphere at room temperature. After the removal of the catalyst by filtration and evaporation of the ethyl acetate under reduced pressure, the residue was then dissolved in hot methylene chloride and the solution was allowed to cool to -10 °C. It gave a white crystalline solid which was filtered off (4.8 g, 13.48 mmol, yield 97%). Crystals of I were grown from a solution of acetone by slow evaporation technique at room temperature. Anal. Calc. for C₂₁H₂₄O₅: C 70.79, H 6.74%. Found: C 70.86, H 6.92%. IR(solid state, cm^-1): ν (C—H_Ar) 3028; ν (C—H_Aliph) 2938; ν (C= O, Aliph.) 1703; ν (C=O, COOH) 1694; ν (C=C, Ar) 1600. ¹H NMR [400 MHz; CDCl₃, (CH₃)₄Si) δ (p.p.m.)]: 1.40 (t, 3H₂₁, CH₃), 1.55 (m, 2H₄, CH₂), 1.74 (m, 2H₃, CH₂), 1.84 (m, 2H₅, CH₂), 2.41 (t, 2H₂, CH₂—COOH), 4.01 (t, 2H₆, O—CH₂), 4.38 (q, 2H₂₀ Me—CH₂—O), 6.98 (d, 2H), 7.55 (d, 2H), 7.62 (d, 2H), 8.07 (d, 2H). ¹³C NMR [100 MHz; CDCl₃, (CH₃)₄Si δ (p.p.m.)]: C₂₁ 14.61, C₄ 24.64, C₃ 25.82, C₅, 29.15, C₂ 34.05, C₂₀ 61.15, C₆ 67.93, C₁₂ and C₈ 115.11, C₁₅ and C₁₇ 126.63, C₁₄ and C₁₈ 128.57, C₉ and C₁₁ 130.29, C₁₀ 132.57, C₁₆ 145.36, C₁₃ 145.36, C₇ 159.48, C₁₉ 166.87, C₁ 179.41.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: XSCANS (Siemens, 1994); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. A view of the centrosymmetric dimer of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A crystal packing view of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

6-[(4'-Ethoxycarbonyl-[1,1'-biphenyl]-4-yl)oxy]hexanoic acid top

Crystal data top

C₂₁H₂₄O₅	F(000) = 760
M_r = 356.4	D_x = 1.243 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 43 reflections
a = 9.111 (2) Å	θ = 9.1–33.6°
b = 14.753 (3) Å	µ = 0.09 mm⁻¹
c = 14.427 (2) Å	T = 298 K
β = 100.785 (14)°	PRISM, colorless
V = 1904.9 (6) Å³	0.5 × 0.5 × 0.4 mm
Z = 4

Data collection top

Siemens P4 diffractometer	R_int = 0.031
Graphite monochromator	θ_max = 24.7°, θ_min = 2.0°
ω scans	h = −1→10
Absorption correction: ψ scan (North et al., 1968)	k = −17→1
T_min = 0.891, T_max = 0.911	l = −16→16
4265 measured reflections	3 standard reflections every 97 reflections
3217 independent reflections	intensity decay: 6%
1628 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.059	w = 1/[σ²(F_o²) + (0.0433P)² + 0.9974P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.171	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.16 e Å⁻³
3217 reflections	Δρ_min = −0.15 e Å⁻³
238 parameters	Extinction correction: SHELXL
0 restraints	Extinction coefficient: 0.0013 (4)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₁H₂₄O₅	V = 1904.9 (6) Å³
M_r = 356.4	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.111 (2) Å	µ = 0.09 mm⁻¹
b = 14.753 (3) Å	T = 298 K
c = 14.427 (2) Å	0.5 × 0.5 × 0.4 mm
β = 100.785 (14)°

Data collection top

Siemens P4 diffractometer	1628 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.031
T_min = 0.891, T_max = 0.911	3 standard reflections every 97 reflections
4265 measured reflections	intensity decay: 6%
3217 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 1.06	Δρ_max = 0.16 e Å⁻³
3217 reflections	Δρ_min = −0.15 e Å⁻³
238 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.8791 (4)	−0.8969 (2)	0.4560 (2)	0.0645 (9)
C2	0.7761 (4)	−0.82076 (19)	0.4252 (2)	0.0672 (9)
H2A	0.6847	−0.8309	0.4491	0.081*
H2B	0.7504	−0.8216	0.3569	0.081*
C3	0.8346 (4)	−0.72759 (19)	0.4559 (3)	0.0712 (10)
H3A	0.9243	−0.7157	0.4309	0.085*
H3B	0.8608	−0.7256	0.5242	0.085*
C4	0.7197 (4)	−0.65502 (19)	0.4220 (2)	0.0721 (10)
H4A	0.6936	−0.6578	0.3538	0.087*
H4B	0.6301	−0.6678	0.4469	0.087*
C5	0.7716 (4)	−0.5605 (2)	0.4506 (3)	0.0790 (11)
H5A	0.8617	−0.5473	0.4265	0.095*
H5B	0.7956	−0.5568	0.5189	0.095*
C6	0.6529 (4)	−0.4906 (2)	0.4133 (3)	0.0748 (10)
H6A	0.6288	−0.4933	0.345	0.09*
H6B	0.5626	−0.5026	0.4378	0.09*
C7	0.6196 (4)	−0.3305 (2)	0.4188 (2)	0.0666 (9)
C8	0.4757 (4)	−0.3335 (2)	0.3664 (2)	0.0688 (9)
H8	0.4334	−0.3885	0.3442	0.083*
C9	0.3949 (4)	−0.2531 (2)	0.3471 (2)	0.0639 (9)
H9	0.2982	−0.2558	0.3121	0.077*
C10	0.4537 (3)	−0.16963 (19)	0.3782 (2)	0.0550 (8)
C11	0.5982 (4)	−0.1695 (2)	0.4320 (2)	0.0655 (9)
H11	0.6409	−0.1148	0.4551	0.079*
C12	0.6788 (4)	−0.2480 (2)	0.4516 (2)	0.0706 (10)
H12	0.7747	−0.2455	0.4876	0.085*
C13	0.3703 (3)	−0.08361 (19)	0.3554 (2)	0.0560 (8)
C14	0.2155 (4)	−0.0809 (2)	0.3260 (2)	0.0724 (10)
H14	0.1615	−0.1347	0.3219	0.087*
C15	0.1407 (4)	−0.0002 (2)	0.3031 (3)	0.0750 (10)
H15	0.0375	−0.0008	0.2835	0.09*
C16	0.2158 (3)	0.0809 (2)	0.3086 (2)	0.0598 (8)
C17	0.3689 (4)	0.0802 (2)	0.3380 (2)	0.0657 (9)
H17	0.4218	0.1345	0.3424	0.079*
C18	0.4447 (3)	−0.0007 (2)	0.3611 (2)	0.0631 (9)
H18	0.5479	0.0004	0.3809	0.076*
C19	0.1335 (4)	0.1663 (2)	0.2828 (2)	0.0699 (9)
C20	0.1574 (4)	0.3263 (2)	0.2690 (3)	0.0835 (11)
H20A	0.0745	0.3366	0.3012	0.1*
H20B	0.1206	0.3301	0.2016	0.1*
C21	0.2767 (4)	0.3949 (2)	0.2988 (3)	0.0951 (13)
H21A	0.3595	0.3827	0.2681	0.143*
H21B	0.3095	0.392	0.366	0.143*
H21C	0.2381	0.4544	0.2815	0.143*
O1	0.8276 (3)	−0.97632 (15)	0.42837 (19)	0.0836 (8)
H1	0.8874	−1.0153	0.4517	0.125*
O2	1.0048 (3)	−0.88595 (14)	0.50571 (18)	0.0784 (7)
O3	0.7090 (3)	−0.40416 (14)	0.44254 (17)	0.0856 (8)
O4	−0.0006 (3)	0.17132 (17)	0.2554 (2)	0.1023 (9)
O5	0.2228 (2)	0.23813 (15)	0.29348 (17)	0.0774 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.060 (2)	0.0473 (19)	0.085 (2)	0.0006 (17)	0.0096 (18)	0.0006 (18)
C2	0.068 (2)	0.0511 (18)	0.081 (2)	0.0086 (17)	0.0084 (18)	0.0084 (17)
C3	0.071 (2)	0.0500 (19)	0.093 (3)	0.0087 (17)	0.0146 (19)	0.0075 (18)
C4	0.085 (2)	0.0500 (19)	0.079 (2)	0.0125 (18)	0.0099 (19)	0.0045 (17)
C5	0.095 (3)	0.0496 (19)	0.089 (3)	0.0114 (19)	0.010 (2)	0.0040 (18)
C6	0.090 (3)	0.0483 (19)	0.086 (3)	0.0049 (18)	0.014 (2)	0.0031 (18)
C7	0.074 (2)	0.0485 (19)	0.075 (2)	0.0104 (18)	0.0078 (18)	−0.0006 (17)
C8	0.078 (2)	0.0464 (18)	0.079 (2)	0.0005 (17)	0.0067 (19)	−0.0051 (17)
C9	0.0571 (19)	0.0562 (19)	0.075 (2)	0.0030 (16)	0.0026 (16)	−0.0032 (17)
C10	0.0584 (19)	0.0447 (17)	0.0610 (19)	0.0020 (15)	0.0088 (15)	−0.0036 (14)
C11	0.066 (2)	0.0474 (18)	0.078 (2)	0.0013 (16)	0.0001 (17)	−0.0009 (16)
C12	0.064 (2)	0.054 (2)	0.086 (3)	0.0002 (17)	−0.0035 (18)	0.0006 (18)
C13	0.0538 (19)	0.0515 (18)	0.062 (2)	0.0040 (15)	0.0105 (15)	−0.0023 (15)
C14	0.056 (2)	0.058 (2)	0.102 (3)	−0.0038 (17)	0.0136 (19)	−0.0019 (19)
C15	0.0468 (19)	0.068 (2)	0.109 (3)	0.0068 (18)	0.0090 (19)	0.000 (2)
C16	0.0518 (19)	0.0542 (19)	0.073 (2)	0.0053 (15)	0.0115 (16)	−0.0018 (16)
C17	0.057 (2)	0.0541 (19)	0.082 (2)	0.0047 (16)	0.0026 (17)	−0.0025 (17)
C18	0.0499 (18)	0.0530 (19)	0.083 (2)	0.0054 (16)	0.0033 (16)	−0.0031 (17)
C19	0.059 (2)	0.066 (2)	0.084 (3)	0.0098 (19)	0.0146 (19)	0.0019 (19)
C20	0.079 (2)	0.061 (2)	0.109 (3)	0.019 (2)	0.016 (2)	0.017 (2)
C21	0.099 (3)	0.063 (2)	0.118 (3)	0.004 (2)	0.008 (3)	0.010 (2)
O1	0.0658 (15)	0.0533 (14)	0.121 (2)	0.0020 (12)	−0.0096 (14)	−0.0037 (14)
O2	0.0587 (14)	0.0538 (14)	0.1133 (19)	0.0005 (11)	−0.0082 (13)	−0.0025 (13)
O3	0.0923 (18)	0.0503 (13)	0.1049 (19)	0.0138 (13)	−0.0050 (15)	−0.0019 (13)
O4	0.0565 (15)	0.0853 (19)	0.160 (3)	0.0175 (14)	0.0074 (16)	0.0118 (18)
O5	0.0668 (15)	0.0565 (14)	0.1050 (19)	0.0122 (12)	0.0063 (13)	0.0084 (13)

Geometric parameters (Å, º) top

C1—O2	1.243 (4)	C10—C13	1.484 (4)
C1—O1	1.296 (3)	C11—C12	1.371 (4)
C1—C2	1.478 (4)	C11—H11	0.93
C2—C3	1.511 (4)	C12—H12	0.93
C2—H2A	0.97	C13—C18	1.393 (4)
C2—H2B	0.97	C13—C14	1.395 (4)
C3—C4	1.513 (4)	C14—C15	1.381 (4)
C3—H3A	0.97	C14—H14	0.93
C3—H3B	0.97	C15—C16	1.373 (4)
C4—C5	1.505 (4)	C15—H15	0.93
C4—H4A	0.97	C16—C17	1.380 (4)
C4—H4B	0.97	C16—C19	1.478 (4)
C5—C6	1.519 (4)	C17—C18	1.388 (4)
C5—H5A	0.97	C17—H17	0.93
C5—H5B	0.97	C18—H18	0.93
C6—O3	1.408 (4)	C19—O4	1.214 (4)
C6—H6A	0.97	C19—O5	1.327 (4)
C6—H6B	0.97	C20—O5	1.446 (4)
C7—O3	1.364 (3)	C20—C21	1.489 (5)
C7—C12	1.378 (4)	C20—H20A	0.97
C7—C8	1.386 (4)	C20—H20B	0.97
C8—C9	1.396 (4)	C21—H21A	0.96
C8—H8	0.93	C21—H21B	0.96
C9—C10	1.384 (4)	C21—H21C	0.96
C9—H9	0.93	O1—H1	0.82
C10—C11	1.398 (4)

O2—C1—O1	122.4 (3)	C11—C10—C13	120.8 (3)
O2—C1—C2	122.6 (3)	C12—C11—C10	121.7 (3)
O1—C1—C2	114.9 (3)	C12—C11—H11	119.1
C1—C2—C3	115.7 (3)	C10—C11—H11	119.1
C1—C2—H2A	108.3	C11—C12—C7	120.9 (3)
C3—C2—H2A	108.3	C11—C12—H12	119.5
C1—C2—H2B	108.3	C7—C12—H12	119.5
C3—C2—H2B	108.3	C18—C13—C14	116.5 (3)
H2A—C2—H2B	107.4	C18—C13—C10	120.9 (3)
C2—C3—C4	111.4 (3)	C14—C13—C10	122.6 (3)
C2—C3—H3A	109.4	C15—C14—C13	121.6 (3)
C4—C3—H3A	109.4	C15—C14—H14	119.2
C2—C3—H3B	109.4	C13—C14—H14	119.2
C4—C3—H3B	109.4	C16—C15—C14	121.3 (3)
H3A—C3—H3B	108	C16—C15—H15	119.4
C5—C4—C3	113.9 (3)	C14—C15—H15	119.4
C5—C4—H4A	108.8	C15—C16—C17	118.4 (3)
C3—C4—H4A	108.8	C15—C16—C19	120.3 (3)
C5—C4—H4B	108.8	C17—C16—C19	121.3 (3)
C3—C4—H4B	108.8	C16—C17—C18	120.6 (3)
H4A—C4—H4B	107.7	C16—C17—H17	119.7
C4—C5—C6	111.5 (3)	C18—C17—H17	119.7
C4—C5—H5A	109.3	C17—C18—C13	121.7 (3)
C6—C5—H5A	109.3	C17—C18—H18	119.1
C4—C5—H5B	109.3	C13—C18—H18	119.1
C6—C5—H5B	109.3	O4—C19—O5	123.2 (3)
H5A—C5—H5B	108	O4—C19—C16	124.5 (3)
O3—C6—C5	108.3 (3)	O5—C19—C16	112.4 (3)
O3—C6—H6A	110	O5—C20—C21	107.2 (3)
C5—C6—H6A	110	O5—C20—H20A	110.3
O3—C6—H6B	110	C21—C20—H20A	110.3
C5—C6—H6B	110	O5—C20—H20B	110.3
H6A—C6—H6B	108.4	C21—C20—H20B	110.3
O3—C7—C12	116.1 (3)	H20A—C20—H20B	108.5
O3—C7—C8	124.8 (3)	C20—C21—H21A	109.5
C12—C7—C8	119.0 (3)	C20—C21—H21B	109.5
C7—C8—C9	119.4 (3)	H21A—C21—H21B	109.5
C7—C8—H8	120.3	C20—C21—H21C	109.5
C9—C8—H8	120.3	H21A—C21—H21C	109.5
C10—C9—C8	122.2 (3)	H21B—C21—H21C	109.5
C10—C9—H9	118.9	C1—O1—H1	109.5
C8—C9—H9	118.9	C7—O3—C6	118.7 (3)
C9—C10—C11	116.6 (3)	C19—O5—C20	118.3 (3)
C9—C10—C13	122.5 (3)

O2—C1—C2—C3	1.4 (5)	C18—C13—C14—C15	0.6 (5)
O1—C1—C2—C3	−179.4 (3)	C10—C13—C14—C15	−178.5 (3)
C1—C2—C3—C4	−179.1 (3)	C13—C14—C15—C16	−0.3 (6)
C2—C3—C4—C5	179.9 (3)	C14—C15—C16—C17	−0.1 (5)
C3—C4—C5—C6	179.1 (3)	C14—C15—C16—C19	179.4 (3)
C4—C5—C6—O3	−179.9 (3)	C15—C16—C17—C18	0.2 (5)
O3—C7—C8—C9	179.7 (3)	C19—C16—C17—C18	−179.3 (3)
C12—C7—C8—C9	0.7 (5)	C16—C17—C18—C13	0.2 (5)
C7—C8—C9—C10	0.3 (5)	C14—C13—C18—C17	−0.5 (5)
C8—C9—C10—C11	−1.2 (5)	C10—C13—C18—C17	178.6 (3)
C8—C9—C10—C13	178.0 (3)	C15—C16—C19—O4	−0.4 (6)
C9—C10—C11—C12	1.1 (5)	C17—C16—C19—O4	179.1 (4)
C13—C10—C11—C12	−178.1 (3)	C15—C16—C19—O5	179.1 (3)
C10—C11—C12—C7	−0.1 (5)	C17—C16—C19—O5	−1.4 (5)
O3—C7—C12—C11	−179.9 (3)	C12—C7—O3—C6	178.2 (3)
C8—C7—C12—C11	−0.9 (5)	C8—C7—O3—C6	−0.8 (5)
C9—C10—C13—C18	−159.7 (3)	C5—C6—O3—C7	−178.5 (3)
C11—C10—C13—C18	19.4 (5)	O4—C19—O5—C20	−1.6 (5)
C9—C10—C13—C14	19.3 (5)	C16—C19—O5—C20	178.9 (3)
C11—C10—C13—C14	−161.5 (3)	C21—C20—O5—C19	173.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.80	2.612 (3)	170
C18—H18···O1ⁱⁱ	0.93	2.54	3.460 (4)	173
C6—H6A···Cg1ⁱⁱⁱ	0.97	2.78	3.668 (4)	152

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.80	2.612 (3)	170
C18—H18···O1ⁱⁱ	0.93	2.54	3.460 (4)	173
C6—H6A···Cg1ⁱⁱⁱ	0.97	2.78	3.668 (4)	152

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

Acknowledgements

The authors acknowledge financial support from the VIEP–BUAP Project (LOVD-NAT12–1), PIFI-2012, Programa Anual de Cooperación Académica BUAP–UNAM 2012 and thank A. R. Hernández-Sosa for the crystal preparation.

References

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