14-Angeloyloxycacalohastine from Psacalium peltatum

Rojano-Vilchis, N.; Hernández-Ortega, S.; Jimenez-Estrada, M.; Torres Avilez, A.

doi:10.1107/S1600536812004199

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o672-o673

doi:10.1107/S1600536812004199

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14-Angeloyloxycacalohastine from Psacalium peltatum

Nadia Rojano-Vilchis,^a Simón Hernández-Ortega,^a ^* Manuel Jimenez-Estrada ^a and Armando Torres Avilez ^a

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, DF 04510, Mexico
^*Correspondence e-mail: simonho@unam.mx

(Received 31 October 2011; accepted 31 January 2012; online 10 February 2012)

The title compound [systematic name: (9-methoxy-3,5-dimethyl-5,6-dihydronaphtho[2,3-b]furan-4-yl)methyl 2-methylbut-2-enoate], C₂₁H₂₄O₄, was isolated from matarique, or Psacalium peltatum (Kunth). The structure is almost planar. The angeloyloxy group makes an angle of 62.08 (2)° with the furanoeremophilane skeleton. The carbonyl O atom is disordered between two positions with a 76:24 ratio. The molecules in the crystal are joined by very weak C—H—O interactions in the ac plane.

Related literature

For fundamental background information, see: Romo de Vivar et al. (2007 ). For biological activity, see: Acevedo-Quiroz et al. (2008 ); Alarcón-Aguilar et al. (2000 ); Bye et al. (1995 ); Contreras-Weber et al. (2002 ); Jimenez-Estrada et al. (2006 ). For compound isolation, see: Abdo et al. (1992 ); Bohlmann et al. (1977 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₂₄O₄
M_r = 340.40
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.1627 (17) Å
b = 10.276 (2) Å
c = 24.605 (6) Å
V = 1811.1 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.40 × 0.40 × 0.40 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
20061 measured reflections
1945 independent reflections
1701 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.095
S = 1.12
1945 reflections
241 parameters
21 restraints
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2ⁱ	0.97	2.62	3.536 (3)	157
C6—H6B⋯O4ⁱⁱ	0.97	2.61	3.42 (2)	142
Symmetry codes: (i) x+1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ .

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812004199/aa2037sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004199/aa2037Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812004199/aa2037Isup3.cml

checkCIF report

Comment top

The sesquiterpenes knows as eremophilanes contain in its basis skeleton a decalin system and most of them are found as furanoeremophilanes (Romo de Vivar et al., 2007). Psacalium peltatum (Kunth) Cass., is an endemic medicinal plant, a member of matarique complex, widely distributed in the central part of Mexico. The roots of P. peltatum have been shown biological activities (Alarcón-Aguilar et al., 2000; Bye et al., 1995; Contreras-Weber et al., 2002). Sesquiterpenes as cacalol and cacalone, isolated from P. decompositum, have been shown a clear inhibition of edema with a dose dependent in anti-inflammatory effect using in vivo models (Jimenez-Estrada et al., 2006). Even more, cacalone in a natural mixture with epi-cacalone reported the highest anti-inflammatory effect using in vivo 12-O-tetradecanoylphorbol-13-acetate (TPA) model (Acevedo-Quiroz, et al., 2008). Although the title compound has been isolated from several species of Senecio inaequidens, S. othonnae (Bohlmann et al., 1977) and S. canescens (Abdo et al., 1992), no report on the crystal structure determination of this compound has appeared. Therefore, due to this lack of data, the x-ray crystal structure determination of 14-angeloyloxycacalohastine was made.

14-Angeloyloxycacalohastine (I) has a furanoeremophilane skeleton (Fig. 1). Bond lengths and angles in (I) exhibit normal values (Allen et al., 1987). The structure is almost planar with C6 and C7 atoms out of the plane, forming a dihedral angle of 26.9 (1)° between central benzene ring and C4—C5—C6—C7 atoms. The angeloyloxy frame is almost perpendicular making a dihedral angle of 62.08 (2) to the furanoeremophilane skeleton. In absence of donor H atoms is noteworthy the fact that in the crystal structure, the molecules are linked by weak C—H···O intermolecular interaction (Table 1).

Related literature top

For fundamental [background information?], see: Romo de Vivar et al. (2007). For biological activity, see: Acevedo-Quiroz et al. (2008); Alarcón-Aguilar et al. (2000); Bye et al. (1995); Contreras-Weber et al. (2002); Jimenez-Estrada et al. (2006). For compound isolation, see: Abdo et al. (1992); Bohlmann et al. (1977). For bond-length data, see: Allen et al. (1987).

Experimental top

Roots of Psacalium peltatum (Kunth) Cass., were collected from pine-oak forest of Mineral del Chico, Hidalgo, Mexico]. A voucher specimen was deposited at the National Herbarium (MEXU 1138692) of the Instituto of Biologia, UNAM, Mexico. Air-dried and powdered roots of P. peltatum were sequentially extracted with n-hexane by exhaustive maceration (3 × 2 l), at room temperature. Hexane extract of roots from P. peltatum, was separated in a chromatoghraphic column by elution with hexane - ethyl acetate in gradient mixture. 14-Angeloyloxycacalohastine was isolated from the fraction eluted by hexane.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of I with the numbering scheme. The thermal ellipsoids are drawn at 40% probability level. The disordered O4A atom was omitted for clarity.

(9-methoxy-3,5-dimethyl-5,6-dihydronaphtho[2,3-b]furan-4-yl)methyl 2-methylbut-2-enoate top

Crystal data top

C₂₁H₂₄O₄	F(000) = 728
M_r = 340.40	D_x = 1.248 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9953 reflections
a = 7.1627 (17) Å	θ = 2.6–25.1°
b = 10.276 (2) Å	µ = 0.09 mm⁻¹
c = 24.605 (6) Å	T = 298 K
V = 1811.1 (7) Å³	Prism, colourless
Z = 4	0.40 × 0.40 × 0.40 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1701 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 25.4°, θ_min = 2.2°
Detector resolution: 0.83 pixels mm^-1	h = −8→8
ω scans	k = −12→12
20061 measured reflections	l = −29→29
1945 independent 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0598P)²] where P = (F_o² + 2F_c²)/3
1945 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 0.15 e Å⁻³
21 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₁H₂₄O₄	V = 1811.1 (7) Å³
M_r = 340.40	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.1627 (17) Å	µ = 0.09 mm⁻¹
b = 10.276 (2) Å	T = 298 K
c = 24.605 (6) Å	0.40 × 0.40 × 0.40 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1701 reflections with I > 2σ(I)
20061 measured reflections	R_int = 0.037
1945 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	21 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.12	Δρ_max = 0.15 e Å⁻³
1945 reflections	Δρ_min = −0.15 e Å⁻³
241 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
O1	0.2416 (2)	0.31693 (16)	0.75432 (6)	0.0714 (5)
O2	−0.0374 (2)	0.52184 (18)	0.78161 (7)	0.0781 (5)
O3	0.6537 (2)	0.35107 (13)	0.92670 (5)	0.0575 (4)
C2	0.4000 (4)	0.2430 (2)	0.75866 (9)	0.0744 (7)
H2	0.4239	0.1717	0.7364	0.089*
C3	0.5167 (3)	0.2821 (2)	0.79734 (9)	0.0609 (6)
C4	0.4777 (3)	0.48417 (18)	0.86340 (7)	0.0474 (5)
C5	0.3937 (4)	0.6883 (2)	0.91708 (8)	0.0600 (6)
H5	0.4798	0.6518	0.9440	0.072*
C6	0.2181 (4)	0.7334 (2)	0.94676 (10)	0.0741 (7)
H6A	0.1798	0.6668	0.9723	0.089*
H6B	0.2463	0.8117	0.9672	0.089*
C7	0.0626 (4)	0.7604 (2)	0.90877 (11)	0.0724 (7)
H7	−0.0248	0.8239	0.9176	0.087*
C8	0.0457 (3)	0.6957 (2)	0.86251 (10)	0.0618 (6)
H8	−0.0526	0.7154	0.8392	0.074*
C9	0.1341 (3)	0.5079 (2)	0.80519 (8)	0.0529 (5)
C10	0.2624 (3)	0.4122 (2)	0.79325 (7)	0.0521 (5)
C11	0.4302 (3)	0.39708 (18)	0.82102 (7)	0.0487 (5)
C12	0.3504 (3)	0.58296 (18)	0.87563 (7)	0.0464 (5)
C13	0.1786 (3)	0.59388 (19)	0.84724 (7)	0.0500 (5)
C14	0.6933 (4)	0.2148 (3)	0.81219 (10)	0.0830 (8)
H14A	0.7065	0.1375	0.7907	0.124*
H14B	0.6903	0.1919	0.8500	0.124*
H14C	0.7971	0.2717	0.8055	0.124*
C15	0.6592 (3)	0.4671 (2)	0.89264 (8)	0.0561 (5)
H15A	0.7597	0.4593	0.8664	0.067*
H15B	0.6836	0.5429	0.9150	0.067*
C16	0.4913 (4)	0.8027 (2)	0.88907 (12)	0.0783 (8)
H16A	0.4144	0.8343	0.8600	0.117*
H16B	0.6091	0.7743	0.8747	0.117*
H16C	0.5116	0.8712	0.9150	0.117*
C17	0.6327 (3)	0.3665 (2)	0.97976 (9)	0.0557 (5)
O4	0.5953 (19)	0.4714 (3)	0.99988 (18)	0.074 (2)	0.76 (3)
O4A	0.697 (5)	0.4664 (12)	0.9991 (6)	0.071 (4)	0.24 (3)
C18	0.6328 (3)	0.2407 (2)	1.00916 (8)	0.0562 (5)
C19	0.6373 (3)	0.2364 (2)	1.06292 (10)	0.0677 (6)
H19	0.6366	0.1532	1.0778	0.081*
C20	0.6433 (5)	0.3438 (3)	1.10315 (9)	0.0836 (8)
H20A	0.5185	0.3719	1.1111	0.125*
H20B	0.7133	0.4153	1.0885	0.125*
H20C	0.7021	0.3138	1.1359	0.125*
C21	0.6300 (4)	0.1180 (2)	0.97545 (11)	0.0767 (7)
H21A	0.6139	0.0440	0.9988	0.115*
H21B	0.7457	0.1099	0.9561	0.115*
H21C	0.5285	0.1219	0.9500	0.115*
C22	−0.0716 (4)	0.4709 (3)	0.72916 (10)	0.0860 (8)
H22A	−0.0871	0.3783	0.7314	0.129*
H22B	0.0322	0.4906	0.7059	0.129*
H22C	−0.1830	0.5093	0.7146	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0921 (12)	0.0633 (10)	0.0588 (9)	0.0009 (10)	−0.0122 (9)	−0.0173 (8)
O2	0.0667 (10)	0.0908 (12)	0.0767 (11)	0.0047 (10)	−0.0186 (9)	−0.0119 (10)
O3	0.0778 (9)	0.0467 (7)	0.0479 (7)	0.0093 (8)	−0.0067 (8)	0.0009 (6)
C2	0.111 (2)	0.0586 (14)	0.0541 (13)	0.0083 (16)	0.0060 (14)	−0.0168 (11)
C3	0.0824 (15)	0.0526 (12)	0.0477 (11)	0.0086 (12)	0.0124 (11)	−0.0027 (10)
C4	0.0607 (12)	0.0424 (10)	0.0390 (10)	−0.0013 (10)	0.0045 (9)	0.0044 (8)
C5	0.0849 (16)	0.0449 (11)	0.0501 (11)	0.0098 (12)	−0.0100 (11)	−0.0052 (9)
C6	0.115 (2)	0.0514 (13)	0.0554 (12)	0.0123 (14)	0.0105 (13)	−0.0075 (11)
C7	0.0786 (16)	0.0509 (13)	0.0878 (18)	0.0144 (14)	0.0141 (14)	−0.0071 (13)
C8	0.0660 (14)	0.0470 (11)	0.0724 (14)	0.0065 (12)	0.0023 (12)	0.0059 (11)
C9	0.0608 (12)	0.0493 (11)	0.0486 (10)	−0.0041 (11)	−0.0022 (10)	0.0068 (9)
C10	0.0702 (13)	0.0453 (11)	0.0407 (9)	−0.0046 (11)	0.0000 (10)	−0.0025 (9)
C11	0.0669 (12)	0.0402 (10)	0.0389 (9)	0.0001 (10)	0.0074 (9)	0.0027 (8)
C12	0.0636 (12)	0.0372 (9)	0.0385 (9)	−0.0001 (10)	0.0013 (9)	0.0035 (8)
C13	0.0648 (12)	0.0396 (10)	0.0455 (10)	−0.0014 (10)	0.0036 (10)	0.0069 (8)
C14	0.101 (2)	0.0752 (17)	0.0732 (16)	0.0340 (16)	0.0106 (15)	−0.0099 (13)
C15	0.0649 (12)	0.0520 (12)	0.0514 (11)	0.0023 (12)	0.0032 (10)	0.0045 (10)
C16	0.0901 (18)	0.0530 (13)	0.0918 (18)	−0.0111 (14)	−0.0088 (15)	−0.0155 (13)
C17	0.0678 (13)	0.0483 (12)	0.0509 (11)	0.0002 (11)	−0.0043 (11)	−0.0024 (9)
O4	0.123 (6)	0.0456 (13)	0.0548 (15)	0.0098 (19)	0.006 (2)	−0.0040 (11)
O4A	0.105 (11)	0.050 (4)	0.059 (5)	0.003 (6)	−0.020 (6)	−0.009 (4)
C18	0.0589 (13)	0.0493 (11)	0.0603 (13)	0.0018 (11)	−0.0077 (10)	0.0068 (10)
C19	0.0669 (14)	0.0678 (14)	0.0685 (14)	0.0039 (13)	−0.0034 (12)	0.0160 (12)
C20	0.099 (2)	0.0994 (19)	0.0529 (13)	0.0107 (19)	−0.0019 (14)	0.0008 (13)
C21	0.0969 (19)	0.0458 (13)	0.0873 (16)	0.0053 (13)	−0.0173 (16)	0.0029 (12)
C22	0.0881 (18)	0.105 (2)	0.0646 (14)	−0.0133 (19)	−0.0220 (14)	0.0098 (14)

Geometric parameters (Å, º) top

O1—C2	1.370 (3)	C10—C11	1.392 (3)
O1—C10	1.378 (2)	C12—C13	1.420 (3)
O2—C9	1.366 (3)	C14—H14A	0.9600
O2—C22	1.414 (3)	C14—H14B	0.9600
O3—C17	1.324 (2)	C14—H14C	0.9600
O3—C15	1.458 (2)	C15—H15A	0.9700
C2—C3	1.329 (3)	C15—H15B	0.9700
C2—H2	0.9300	C16—H16A	0.9600
C3—C11	1.456 (3)	C16—H16B	0.9600
C3—C14	1.487 (4)	C16—H16C	0.9600
C4—C12	1.397 (3)	C17—O4	1.216 (3)
C4—C11	1.415 (3)	C17—O4A	1.221 (8)
C4—C15	1.497 (3)	C17—C18	1.481 (3)
C5—C12	1.519 (3)	C18—C19	1.324 (3)
C5—C6	1.527 (4)	C18—C21	1.510 (3)
C5—C16	1.532 (4)	C19—C20	1.483 (4)
C5—H5	0.9800	C19—H19	0.9300
C6—C7	1.480 (4)	C20—H20A	0.9600
C6—H6A	0.9700	C20—H20B	0.9600
C6—H6B	0.9700	C20—H20C	0.9600
C7—C8	1.324 (3)	C21—H21A	0.9600
C7—H7	0.9300	C21—H21B	0.9600
C8—C13	1.463 (3)	C21—H21C	0.9600
C8—H8	0.9300	C22—H22A	0.9600
C9—C10	1.377 (3)	C22—H22B	0.9600
C9—C13	1.397 (3)	C22—H22C	0.9600

C2—O1—C10	104.50 (17)	C3—C14—H14B	109.5
C9—O2—C22	120.3 (2)	H14A—C14—H14B	109.5
C17—O3—C15	118.19 (16)	C3—C14—H14C	109.5
C3—C2—O1	114.2 (2)	H14A—C14—H14C	109.5
C3—C2—H2	122.9	H14B—C14—H14C	109.5
O1—C2—H2	122.9	O3—C15—C4	110.43 (18)
C2—C3—C11	105.3 (2)	O3—C15—H15A	109.6
C2—C3—C14	124.8 (2)	C4—C15—H15A	109.6
C11—C3—C14	129.9 (2)	O3—C15—H15B	109.6
C12—C4—C11	117.49 (19)	C4—C15—H15B	109.6
C12—C4—C15	123.27 (18)	H15A—C15—H15B	108.1
C11—C4—C15	119.24 (19)	C5—C16—H16A	109.5
C12—C5—C6	111.7 (2)	C5—C16—H16B	109.5
C12—C5—C16	109.76 (18)	H16A—C16—H16B	109.5
C6—C5—C16	111.0 (2)	C5—C16—H16C	109.5
C12—C5—H5	108.1	H16A—C16—H16C	109.5
C6—C5—H5	108.1	H16B—C16—H16C	109.5
C16—C5—H5	108.1	O4—C17—O3	122.2 (3)
C7—C6—C5	112.01 (19)	O4A—C17—O3	116.2 (10)
C7—C6—H6A	109.2	O4—C17—C18	125.1 (3)
C5—C6—H6A	109.2	O4A—C17—C18	122.9 (6)
C7—C6—H6B	109.2	O3—C17—C18	112.17 (19)
C5—C6—H6B	109.2	C19—C18—C17	121.1 (2)
H6A—C6—H6B	107.9	C19—C18—C21	121.5 (2)
C8—C7—C6	121.2 (2)	C17—C18—C21	117.43 (18)
C8—C7—H7	119.4	C18—C19—C20	130.0 (2)
C6—C7—H7	119.4	C18—C19—H19	115.0
C7—C8—C13	121.4 (2)	C20—C19—H19	115.0
C7—C8—H8	119.3	C19—C20—H20A	109.5
C13—C8—H8	119.3	C19—C20—H20B	109.5
O2—C9—C10	125.7 (2)	H20A—C20—H20B	109.5
O2—C9—C13	116.9 (2)	C19—C20—H20C	109.5
C10—C9—C13	117.22 (19)	H20A—C20—H20C	109.5
O1—C10—C9	125.70 (19)	H20B—C20—H20C	109.5
O1—C10—C11	110.82 (18)	C18—C21—H21A	109.5
C9—C10—C11	123.45 (19)	C18—C21—H21B	109.5
C10—C11—C4	119.90 (19)	H21A—C21—H21B	109.5
C10—C11—C3	105.17 (19)	C18—C21—H21C	109.5
C4—C11—C3	134.9 (2)	H21A—C21—H21C	109.5
C4—C12—C13	121.13 (17)	H21B—C21—H21C	109.5
C4—C12—C5	121.96 (19)	O2—C22—H22A	109.5
C13—C12—C5	116.80 (18)	O2—C22—H22B	109.5
C9—C13—C12	120.79 (19)	H22A—C22—H22B	109.5
C9—C13—C8	119.6 (2)	O2—C22—H22C	109.5
C12—C13—C8	119.60 (18)	H22A—C22—H22C	109.5
C3—C14—H14A	109.5	H22B—C22—H22C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.97	2.62	3.536 (3)	157
C6—H6B···O4ⁱⁱ	0.97	2.61	3.42	142

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+3/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄O₄
M_r	340.40
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.1627 (17), 10.276 (2), 24.605 (6)
V (Å³)	1811.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.40 × 0.40

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20061, 1945, 1701
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.095, 1.12
No. of reflections	1945
No. of parameters	241
No. of restraints	21
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.97	2.622	3.536 (3)	156.9
C6—H6B···O4ⁱⁱ	0.97	2.605	3.42	141.7

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+3/2, −z+2.

Acknowledgements

NRV acknowledges a scholarship and financial support provided by the Conseja Nacional de Ciencia y Tecnología (CONACyT: 101038) and the Programa en Ciencias Biologicas of the Universidad Nacional Autónoma de México (UNAM).

References

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