Tetra­kis(μ-acetato-κ2O:O′)-bis­[(3-pyridine­carboxaldehyde-κN′)]dicopper(II)(Cu—Cu)

Cruz-Enriquez, A.; Baez-Castro, A.; Höpfl, H.; Parra-Hake, M.; Campos-Gaxiola, J.J.

doi:10.1107/S1600536812041074

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages m1339-m1340

doi:10.1107/S1600536812041074

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Tetrakis(μ-acetato-κ²O:O′)-bis[(3-pyridinecarboxaldehyde-κN′)]dicopper(II)(Cu—Cu)

Adriana Cruz-Enriquez,^a Alberto Baez-Castro,^a Herbert Höpfl,^b Miguel Parra-Hake ^c and Jose J. Campos-Gaxiola ^a ^*

^aFacultad de Ingenieria Mochis, Universidad Autonoma de Sinaloa, Fuente Poseidon y Prol. A. Flores S/N, CP 81223, C.U. Los Mochis, Sinaloa, Mexico, ^bCentro de Investigaciones Quimicas, Universidad Autonoma del Estado de Morelos, Av. Universidad 1001, CP 62210, Cuernavaca, Morelos, Mexico, and ^cCentro de Graduados del Instituto Tecnologico de Tijuana, Blvd. Industrial S/N Col. Otay, CP 22500, Tijuana, B.C., Mexico
^*Correspondence e-mail: gaxiolajose@yahoo.com.mx

(Received 27 September 2012; accepted 30 September 2012; online 10 October 2012)

The binuclear title compound, [Cu₂(CH₃CO₂)₄(C₆H₅NO)], is located about a center of inversion. The Cu^II atoms are connected [Cu—Cu = 2.6134 (5) Å] and bridged by four acetate ligands. Their distorted octahedral coordination geometry is completed by a terminal pyridine N atom of a 3-pyridincarboxaldehyde ligand. In the crystal, the complex molecules are linked by C—H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to the ab plane. These networks are linked via C—H⋯O hydrogen bonds involving inversion-related 3-pyridinecarboxaldehyde ligands, forming a three dimensional supramolecular architecture.

Related literature

For related paddle-wheel structures, see: Aakeröy et al. (2003 ); Sieroń (2004 ); Fairuz et al. (2011 ); Trivedi et al. (2011 ). For Cu⋯Cu separations in related structures, see: Seco et al. (2004 ); Asem et al. (2011 ).

Experimental

Crystal data

[Cu₂(C₂H₃O₂)₄(C₆H₅NO)]
M_r = 577.48
Triclinic, $[P \overline 1]$
a = 7.4099 (6) Å
b = 8.4298 (7) Å
c = 10.0254 (8) Å
α = 100.353 (1)°
β = 108.975 (1)°
γ = 98.679 (1)°
V = 567.61 (8) Å³
Z = 1
Mo Kα radiation
μ = 1.93 mm⁻¹
T = 100 K
0.48 × 0.21 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.448, T_max = 0.720
4118 measured reflections
1980 independent reflections
1921 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.068
S = 1.10
1980 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.93	2.43	3.262 (4)	148
C6—H6⋯O3ⁱⁱ	0.93	2.56	3.449 (4)	159
C8—H8B⋯O3ⁱⁱⁱ	0.96	2.60	3.542 (3)	168
C10—H10C⋯O2^iv	0.96	2.48	3.420 (4)	167
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+2, -y+1, -z+2; (iii) -x+1, -y, -z+2; (iv) x-1, y, z.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus-NT (Bruker, 2001 ); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012 ) and Mercury (Macrae et al. 2008 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536812041074/su2505sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041074/su2505Isup2.hkl

checkCIF report

Comment top

Bridged binuclear copper(II) complexes have been the subject of continuing interest because of their magneto-structural properties. Pyridine ligands have the potential to be used in the synthesis of supramolecular materials, particularly transition metal coordination polymers. Herein, we report on the synthesis and crystal structure of the new binuclear Cu₂(OAc)₄L₂ paddle-wheel complex with L = 3-pyridincarboxaldehyde.

The title complex (Fig. 1) is structurally similar to paddle-wheel structures of other Cu₂(OAc)₄L₂ complexes (Aakeröy et al., 2003; Fairuz et al., 2011; Seco et al., 2004; Sieroń, 2004; Trivedi et al., 2011). The binuclear molecule lies about an inversion center. Attached to the Cu₂(OAc)₄ core unit there are two apical pyridine groups from 3-pyridincarboxaldehyde ligands. The Cu—O distances [which vary from 1.9625 (19) - 1.9692 (17) Å], the Cu1—N1 distance [2.189 (2) Å], and the corresponding bond angles are consistent with the structurally similar Cu^IIcomplexes mentioned above. Although the Cu1—Cu1ⁱ separation of 2.6134 (6) Å [symmetry code: (i) -x+1, -y+1, -z+2] is towards the lower limit, it is within the range of values reported for other Cu^II paddle-wheel structures (Sieroń, 2004; Asem et al., 2011).

In the crystal, the complex molecules are linked by C—H···O hydrogen bonds to form two-dimensional networks lying parallel to the ab plane (Table 1 and Fig. 2). These networks are linked via C-H···O hydrogen bonds involving inversion related 3-pyridincarboxaldehyde ligands forming a three dimensional supramolecular architecture (Table 1).

Related literature top

For related paddle-wheel structures, see: Aakeröy et al. (2003); Sieroń (2004); Fairuz et al. (2011); Trivedi et al. (2011). For Cu···Cu separations in related compounds, see: Seco et al. (2004); Asem et al. (2011).

Experimental top

A mixture of 3-pyridincarboxaldehyde (0.05 g, 0.466 mmol) and Cu(CH₃COO)₂H₂O (0.093 g, 0.466 mmol) dissolved in methanol (5 ml) was stirred for 2 h at room temperature to give a blue solution. After one week, blue crystals suitable for X-ray diffraction analysis had been formed, which were collected by filtration [Yield: 65%]. Spectroscopic and TGA data are given in the archived CIF.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus-NT (Bruker, 2001); data reduction: SAINT-Plus-NT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al. 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title complex, showing the atom-labelling scheme. The displacement ellipsoids are drawn at the 50% probability level. The unlabelled atoms are related by the symmetry code: -x+1, -y+1, -z+2.
	Fig. 2. Perspective view of a fragment of the two-dimensional supramolecular network with the C—H···O hydrogen bonds shown as dashed lines.

Tetrakis(µ-acetato-κ²O:O')-bis[(3-pyridinecarboxaldehyde- κN')]dicopper(II)(Cu—Cu) top

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₆H₅NO)]	Z = 1
M_r = 577.48	F(000) = 294
Triclinic, P1	D_x = 1.689 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4099 (6) Å	Cell parameters from 3727 reflections
b = 8.4298 (7) Å	θ = 2.5–28.3°
c = 10.0254 (8) Å	µ = 1.93 mm⁻¹
α = 100.353 (1)°	T = 100 K
β = 108.975 (1)°	Rectangular prism, blue
γ = 98.679 (1)°	0.48 × 0.21 × 0.17 mm
V = 567.61 (8) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	1980 independent reflections
Radiation source: fine-focus sealed tube	1921 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
phi and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.448, T_max = 0.720	k = −8→10
4118 measured reflections	l = −11→11

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.068	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0297P)² + 0.5378P] where P = (F_o² + 2F_c²)/3
1980 reflections	(Δ/σ)_max = 0.001
156 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₆H₅NO)]	γ = 98.679 (1)°
M_r = 577.48	V = 567.61 (8) Å³
Triclinic, P1	Z = 1
a = 7.4099 (6) Å	Mo Kα radiation
b = 8.4298 (7) Å	µ = 1.93 mm⁻¹
c = 10.0254 (8) Å	T = 100 K
α = 100.353 (1)°	0.48 × 0.21 × 0.17 mm
β = 108.975 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1980 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1921 reflections with I > 2σ(I)
T_min = 0.448, T_max = 0.720	R_int = 0.018
4118 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.068	H-atom parameters constrained
S = 1.10	Δρ_max = 0.41 e Å⁻³
1980 reflections	Δρ_min = −0.36 e Å⁻³
156 parameters

Special details top

Experimental. Spectroscopic and TGA data for the title compound: IR (KBr, cm^-1): 3273, 3076, 2935, 2871, 1705, 1615, 1440, 1218, 1035, 690; TGA Calcd. for 2(C₆H₅NO): 37.07. Found: 37.53% (303 - 473 K).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
Cu1	0.56063 (4)	0.57222 (3)	0.91251 (3)	0.0137 (1)
O1	1.1945 (3)	0.9402 (3)	0.6523 (2)	0.0382 (7)
O2	0.6188 (3)	0.3569 (2)	0.85203 (19)	0.0232 (5)
O3	0.5192 (3)	0.2340 (2)	1.00330 (18)	0.0216 (5)
O4	0.2879 (2)	0.4870 (2)	0.77698 (18)	0.0235 (5)
O5	0.1855 (2)	0.3580 (2)	0.92442 (18)	0.0243 (5)
N1	0.6613 (3)	0.6761 (2)	0.7573 (2)	0.0155 (6)
C1	0.8501 (4)	0.7380 (3)	0.7858 (2)	0.0192 (7)
C2	0.9167 (4)	0.8063 (3)	0.6899 (3)	0.0203 (7)
C3	0.7811 (4)	0.8086 (3)	0.5568 (3)	0.0215 (8)
C4	0.5870 (4)	0.7427 (3)	0.5258 (3)	0.0223 (7)
C5	0.5325 (4)	0.6786 (3)	0.6284 (3)	0.0198 (7)
C6	1.1288 (4)	0.8746 (4)	0.7290 (3)	0.0306 (9)
C7	0.5933 (3)	0.2365 (3)	0.9070 (2)	0.0172 (7)
C8	0.6587 (4)	0.0847 (3)	0.8539 (3)	0.0230 (8)
C9	0.1593 (3)	0.3988 (3)	0.8058 (2)	0.0168 (7)
C10	−0.0418 (4)	0.3371 (3)	0.6896 (3)	0.0242 (8)
H1	0.94130	0.73520	0.87420	0.0230*
H3	0.82120	0.85370	0.49020	0.0260*
H4	0.49320	0.74120	0.43710	0.0270*
H5	0.40040	0.63520	0.60690	0.0240*
H6	1.21540	0.86630	0.81720	0.0370*
H8A	0.58970	0.04310	0.75100	0.0340*
H8B	0.63120	0.00150	0.90290	0.0340*
H8C	0.79690	0.11290	0.87380	0.0340*
H10A	−0.06390	0.22020	0.65090	0.0360*
H10B	−0.05110	0.39310	0.61300	0.0360*
H10C	−0.13850	0.35880	0.73070	0.0360*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0144 (2)	0.0153 (2)	0.0134 (2)	0.0035 (1)	0.0066 (1)	0.0051 (1)
O1	0.0245 (10)	0.0576 (14)	0.0370 (11)	0.0009 (9)	0.0121 (9)	0.0276 (10)
O2	0.0356 (10)	0.0191 (9)	0.0269 (9)	0.0118 (8)	0.0217 (8)	0.0106 (7)
O3	0.0309 (10)	0.0186 (9)	0.0244 (9)	0.0100 (7)	0.0174 (8)	0.0096 (7)
O4	0.0165 (9)	0.0326 (10)	0.0188 (8)	−0.0007 (8)	0.0039 (7)	0.0096 (7)
O5	0.0168 (9)	0.0343 (10)	0.0200 (9)	0.0000 (7)	0.0050 (7)	0.0103 (8)
N1	0.0195 (10)	0.0129 (10)	0.0157 (9)	0.0028 (8)	0.0083 (8)	0.0042 (8)
C1	0.0222 (13)	0.0214 (12)	0.0162 (11)	0.0070 (10)	0.0069 (10)	0.0085 (9)
C2	0.0211 (13)	0.0213 (13)	0.0226 (12)	0.0068 (10)	0.0102 (10)	0.0096 (10)
C3	0.0266 (14)	0.0243 (13)	0.0180 (12)	0.0052 (11)	0.0125 (11)	0.0079 (10)
C4	0.0231 (13)	0.0276 (14)	0.0146 (11)	0.0042 (11)	0.0042 (10)	0.0072 (10)
C5	0.0194 (12)	0.0199 (12)	0.0190 (12)	0.0018 (10)	0.0072 (10)	0.0042 (10)
C6	0.0220 (14)	0.0439 (17)	0.0291 (14)	0.0053 (12)	0.0082 (12)	0.0202 (13)
C7	0.0139 (11)	0.0195 (12)	0.0154 (11)	0.0018 (9)	0.0029 (9)	0.0033 (9)
C8	0.0263 (14)	0.0195 (13)	0.0260 (13)	0.0067 (10)	0.0128 (11)	0.0051 (10)
C9	0.0161 (12)	0.0176 (12)	0.0166 (11)	0.0048 (10)	0.0068 (10)	0.0018 (9)
C10	0.0187 (13)	0.0334 (15)	0.0181 (12)	0.0028 (11)	0.0053 (10)	0.0053 (10)

Geometric parameters (Å, º) top

Cu1—O2	1.9643 (19)	C3—C4	1.371 (4)
Cu1—O4	1.9677 (17)	C4—C5	1.385 (4)
Cu1—N1	2.189 (2)	C7—C8	1.505 (4)
Cu1—O3ⁱ	1.9625 (19)	C9—C10	1.506 (4)
Cu1—O5ⁱ	1.9692 (17)	C1—H1	0.9300
O1—C6	1.204 (4)	C3—H3	0.9300
O2—C7	1.257 (3)	C4—H4	0.9300
O3—C7	1.258 (3)	C5—H5	0.9300
O4—C9	1.260 (3)	C6—H6	0.9300
O5—C9	1.260 (3)	C8—H8A	0.9600
N1—C1	1.333 (4)	C8—H8B	0.9600
N1—C5	1.340 (3)	C8—H8C	0.9600
C1—C2	1.386 (4)	C10—H10A	0.9600
C2—C3	1.391 (4)	C10—H10B	0.9600
C2—C6	1.483 (4)	C10—H10C	0.9600

O2—Cu1—O4	89.70 (8)	O3—C7—C8	117.9 (2)
O2—Cu1—N1	92.99 (8)	O4—C9—O5	125.2 (2)
O2—Cu1—O3ⁱ	168.80 (8)	O4—C9—C10	117.59 (19)
O2—Cu1—O5ⁱ	90.47 (8)	O5—C9—C10	117.3 (2)
O4—Cu1—N1	94.72 (7)	N1—C1—H1	118.00
O3ⁱ—Cu1—O4	88.36 (8)	C2—C1—H1	119.00
O4—Cu1—O5ⁱ	168.89 (7)	C2—C3—H3	121.00
O3ⁱ—Cu1—N1	98.16 (7)	C4—C3—H3	121.00
O5ⁱ—Cu1—N1	96.36 (7)	C3—C4—H4	120.00
O3ⁱ—Cu1—O5ⁱ	89.32 (8)	C5—C4—H4	120.00
Cu1—O2—C7	124.41 (17)	N1—C5—H5	118.00
Cu1ⁱ—O3—C7	121.63 (16)	C4—C5—H5	119.00
Cu1—O4—C9	123.33 (14)	O1—C6—H6	118.00
Cu1ⁱ—O5—C9	122.48 (15)	C2—C6—H6	118.00
Cu1—N1—C1	122.12 (14)	C7—C8—H8A	109.00
Cu1—N1—C5	120.33 (19)	C7—C8—H8B	110.00
C1—N1—C5	117.6 (2)	C7—C8—H8C	109.00
N1—C1—C2	123.1 (2)	H8A—C8—H8B	109.00
C1—C2—C3	118.7 (3)	H8A—C8—H8C	109.00
C1—C2—C6	120.3 (3)	H8B—C8—H8C	110.00
C3—C2—C6	121.0 (3)	C9—C10—H10A	109.00
C2—C3—C4	118.6 (3)	C9—C10—H10B	109.00
C3—C4—C5	119.1 (3)	C9—C10—H10C	110.00
N1—C5—C4	123.1 (3)	H10A—C10—H10B	109.00
O1—C6—C2	123.3 (3)	H10A—C10—H10C	110.00
O2—C7—O3	125.1 (2)	H10B—C10—H10C	109.00
O2—C7—C8	117.1 (2)

O2—Cu1—N1—C1	−82.47 (19)	Cu1—O2—C7—C8	−176.00 (17)
O2—Cu1—N1—C5	97.24 (19)	Cu1—O2—C7—O3	3.4 (3)
O4—Cu1—N1—C1	−172.41 (18)	Cu1ⁱ—O3—C7—O2	−2.2 (3)
O4—Cu1—N1—C5	7.30 (19)	Cu1ⁱ—O3—C7—C8	177.20 (17)
O3ⁱ—Cu1—N1—C1	98.57 (19)	Cu1—O4—C9—O5	2.2 (3)
O3ⁱ—Cu1—N1—C5	−81.72 (19)	Cu1—O4—C9—C10	−177.83 (16)
O5ⁱ—Cu1—N1—C1	8.34 (19)	Cu1ⁱ—O5—C9—O4	−0.1 (3)
O5ⁱ—Cu1—N1—C5	−171.95 (18)	Cu1ⁱ—O5—C9—C10	179.91 (17)
O4—Cu1—O2—C7	−86.4 (2)	Cu1—N1—C1—C2	−179.13 (19)
N1—Cu1—O2—C7	178.9 (2)	C5—N1—C1—C2	1.2 (4)
O5ⁱ—Cu1—O2—C7	82.5 (2)	Cu1—N1—C5—C4	179.93 (19)
O5—Cu1ⁱ—O3—C7	85.16 (19)	C1—N1—C5—C4	−0.4 (4)
O4ⁱ—Cu1ⁱ—O3—C7	−83.97 (19)	N1—C1—C2—C6	179.4 (2)
N1ⁱ—Cu1ⁱ—O3—C7	−178.51 (18)	N1—C1—C2—C3	−0.9 (4)
O2—Cu1—O4—C9	80.85 (19)	C1—C2—C6—O1	−177.5 (3)
N1—Cu1—O4—C9	173.83 (18)	C6—C2—C3—C4	179.5 (3)
O3ⁱ—Cu1—O4—C9	−88.12 (19)	C1—C2—C3—C4	−0.2 (4)
O3—Cu1ⁱ—O5—C9	−86.94 (19)	C3—C2—C6—O1	2.8 (5)
O2ⁱ—Cu1ⁱ—O5—C9	81.86 (19)	C2—C3—C4—C5	0.9 (4)
N1ⁱ—Cu1ⁱ—O5—C9	174.92 (18)	C3—C4—C5—N1	−0.7 (4)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱⁱ	0.93	2.43	3.262 (4)	148
C6—H6···O3ⁱⁱⁱ	0.93	2.56	3.449 (4)	159
C8—H8B···O3^iv	0.96	2.60	3.542 (3)	168
C10—H10C···O2^v	0.96	2.48	3.420 (4)	167

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₂H₃O₂)₄(C₆H₅NO)]
M_r	577.48
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.4099 (6), 8.4298 (7), 10.0254 (8)
α, β, γ (°)	100.353 (1), 108.975 (1), 98.679 (1)
V (Å³)	567.61 (8)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.93
Crystal size (mm)	0.48 × 0.21 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.448, 0.720
No. of measured, independent and observed [I > 2σ(I)] reflections	4118, 1980, 1921
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.068, 1.10
No. of reflections	1980
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.36

Computer programs: SMART (Bruker, 2000), SAINT-Plus-NT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al. 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.43	3.262 (4)	148
C6—H6···O3ⁱⁱ	0.93	2.56	3.449 (4)	159
C8—H8B···O3ⁱⁱⁱ	0.96	2.60	3.542 (3)	168
C10—H10C···O2^iv	0.96	2.48	3.420 (4)	167

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

Acknowledgements

This work was supported financially by the Universidad Autónoma de Sinaloa (PROFAPI 2011/033). ABC thanks the Consejo Nacional de Ciencia y Tecnologia (CONACYT) for support in the form of a scholarship.

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