Cyclo­hexane-1,4-dicarb­oxy­lic acid–pyridinium-4-olate (1/1)

Cruz-Enriquez, A.; Peinado-Guevara, H.J.; Reyes-Marquez, V.; Hopfl, H.; Campos-Gaxiola, J.J.

doi:10.1107/S160053681300754X

organic compounds

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Volume 69| Part 4| April 2013| Page o591

doi:10.1107/S160053681300754X

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Cyclohexane-1,4-dicarboxylic acid–pyridinium-4-olate (1/1)

Adriana Cruz-Enríquez,^a ^* Hector J. Peinado-Guevara,^a Viviana Reyes-Marquez,^b Herbert Höpfl ^b and José J. Campos-Gaxiola ^a

^aFacultad de Ingenieria Mochis, Universidad Autónoma de Sinaloa, Fuente Poseidón y Prol. A. Flores S/N, CP 81223, C.U. Los Mochis, Sinaloa, México, and ^bCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, CP 62210, Cuernavaca, Morelos, México
^*Correspondence e-mail: cenriqueza@yahoo.com.mx

(Received 9 March 2013; accepted 19 March 2013; online 28 March 2013)

In the title adduct, C₅H₅NO·C₈H₁₂O₄, the heterocycle exists in its zwitterionic form. The cyclohexane ring exhibits a chair conformation with the carboxylic acid groups in equatorial and axial orientations. In the crystal, molecules are linked through charge-assisted O—H⋯O⁻, N⁺—H⋯O⁻ and N⁺—H⋯O hydrogen bonds, and an additional series of C—H⋯O contacts, giving a pleated two-dimensional hydrogen-bonded network parallel to (-204).

Related literature

For reports on supramolecular crystal engineering and potential applications of co-crystals, see: Desiraju (1995 ); Simon & Bassoul (2000 ); Weyna et al. (2009 ); Aakeröy et al. (2010 ); Yan et al. (2012 ). For related structures, see: Bhogala et al. (2005 ); Shattock et al. (2008 ); Yu (2012 ).

Experimental

Crystal data

C₅H₅NO·C₈H₁₂O₄
M_r = 267.28
Monoclinic, P 2₁ /c
a = 11.749 (2) Å
b = 11.618 (2) Å
c = 10.8010 (19) Å
β = 115.383 (2)°
V = 1332.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.50 × 0.43 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.95, T_max = 0.98
12552 measured reflections
2345 independent reflections
2229 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.161
S = 1.02
2345 reflections
181 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1′⋯O5	0.84	1.82	2.638 (3)	165
O3—H3′⋯O5ⁱ	0.84	1.76	2.594 (2)	175
N1—H1⋯O4ⁱⁱ	0.84	2.29	2.921 (3)	132
N1—H1⋯O5ⁱⁱⁱ	0.84	2.39	3.038 (3)	134
C1—H1A⋯O2^iv	0.98	2.67	3.625 (4)	162
C11—H11⋯O2ⁱⁱⁱ	0.93	2.62	3.420 (5)	143
C12—H12⋯O4ⁱⁱ	0.93	2.47	3.014 (4)	117
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus-NT (Bruker, 2001 ); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL-NT; 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, global. DOI: 10.1107/S160053681300754X/pk2472sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681300754X/pk2472Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681300754X/pk2472Isup3.cml

checkCIF report

Comment top

The engineering of novel materials via non-covalent synthesis has developed as a very attractive and potential area of research because of its importance in biological systems, molecular recognition (Simon et al., 2000; Aakeröy et al., 2010), pharmaceutical chemistry (Weyna et al., 2009) and materials chemistry (Yan et al., 2012). Aromatic carboxylic acids form reliable supramolecular synthons for the construction of novel organic networks by hydrogen bonding and π-π interactions (Desiraju, 1995), and numerous studies have focused on hydrogen bonding between carboxylic acids and pyridine derivatives (Bhogala et al., 2005; Shattock et al. 2008; Yu, 2012). Herein, we report on the solid-state structure of a 1:1 co-crystal formed between cyclohexane-1,4-dicarboxylic acid and pyridin-4-ol. The molecular components of the title compound are shown in Fig. 1. The asymmetric unit contains one cyclohexane-1,4-dicarboxylic acid and one pyridin-4-ol molecule in the zwitterionic form. The cyclohexane ring exhibits a chair conformation with the carboxylic groups in equatorial and axial orientation, as denoted by the C7—C1—C2—C3 [-177.7 (2)°] and C8—C4—C5—C6 [75.7 (3)°] torsion angles, respectively. In the crystal, the molecular entities are linked through charge-assisted O—H···O^-, N⁺—H···O^- and N⁺—H···O hydrogen bonds and an additional series of C—H···O contacts to give a pleated two-dimensional hydrogen-bonded network parallel to (-204) (Fig. 2, Table 1).

Related literature top

For reports on supramolecular crystal engineering and potential applications of co-crystals, see: Desiraju (1995); Simon & Bassoul (2000); Weyna et al. (2009); Aakeröy et al. (2010); Yan et al. (2012). For related structures, see: Bhogala et al. (2005); Shattock et al. (2008); Yu (2012).

Experimental top

C₅H₅NO.C₈H₁₂O₄ was prepared from a solution of C₅H₅NO (0.05 g, 0.53 mmol) and C₈H₁₂O₄ (0.09 g, 0.53 mmol) in CH₃OH (5 ml), which was stirred for a few minutes at room temperature, giving a clear transparent solution. After evaporation of the solvent, colorless crystals suitable for single-crystal X-ray diffraction had formed in about 51% yield. IR (KBr): 3471, 3276, 3131, 3092, 2937, 2863, 1709, 1632, 1576, 1509, 1416, 1364, 1331, 1316, 1229, 1170, 1001 cm^-1.

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: SHELXTL-NT (Sheldrick, 2008); program(s) used to refine structure: SHELXTL-NT (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 structures of the components in the title compound, showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. View down the c-axis of the two-dimensional hydrogen-bonded supramolecular network formed through O—H···O^-, N⁺—H···O^- and N⁺—H···O and C—H···O interactions.

Cyclohexane-1,4-dicarboxylic acid–pyridinium-4-olate (1/1) top

Crystal data top

C₅H₅NO·C₈H₁₂O₄	F(000) = 568
M_r = 267.28	D_x = 1.333 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5484 reflections
a = 11.749 (2) Å	θ = 2.6–27.4°
b = 11.618 (2) Å	µ = 0.10 mm⁻¹
c = 10.8010 (19) Å	T = 293 K
β = 115.383 (2)°	Rectangular prism, yellow
V = 1332.0 (4) Å³	0.50 × 0.43 × 0.24 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2345 independent reflections
Radiation source: fine-focus sealed tube	2229 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.95, T_max = 0.98	k = −13→13
12552 measured reflections	l = −12→12

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0623P)² + 1.4075P] where P = (F_o² + 2F_c²)/3
2345 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.20 e Å⁻³
3 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₅H₅NO·C₈H₁₂O₄	V = 1332.0 (4) Å³
M_r = 267.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.749 (2) Å	µ = 0.10 mm⁻¹
b = 11.618 (2) Å	T = 293 K
c = 10.8010 (19) Å	0.50 × 0.43 × 0.24 mm
β = 115.383 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2345 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2229 reflections with I > 2σ(I)
T_min = 0.95, T_max = 0.98	R_int = 0.041
12552 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	3 restraints
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.20 e Å⁻³
2345 reflections	Δρ_min = −0.27 e Å⁻³
181 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
O1	0.2230 (2)	0.1930 (2)	0.0632 (2)	0.0663 (6)
H1'	0.162 (2)	0.198 (4)	0.085 (4)	0.099*
O2	0.3186 (2)	0.3059 (3)	0.2412 (3)	0.0898 (9)
O3	0.8439 (2)	0.3327 (2)	0.3413 (2)	0.0733 (7)
H3'	0.901 (3)	0.324 (4)	0.4210 (17)	0.110*
O4	0.7984 (2)	0.15562 (19)	0.3701 (2)	0.0805 (8)
C1	0.4258 (2)	0.2522 (2)	0.1037 (2)	0.0420 (6)
H1A	0.3892	0.2539	0.0033	0.050*
C2	0.5129 (3)	0.3552 (2)	0.1563 (3)	0.0489 (7)
H2A	0.4647	0.4256	0.1246	0.059*
H2B	0.5510	0.3555	0.2557	0.059*
C3	0.6155 (3)	0.3511 (3)	0.1063 (3)	0.0556 (8)
H3A	0.6718	0.4160	0.1442	0.067*
H3B	0.5773	0.3583	0.0073	0.067*
C4	0.6915 (3)	0.2400 (3)	0.1470 (3)	0.0497 (7)
H4	0.7428	0.2374	0.0955	0.060*
C5	0.6058 (3)	0.1347 (3)	0.1039 (3)	0.0557 (8)
H5A	0.5683	0.1283	0.0048	0.067*
H5B	0.6559	0.0662	0.1416	0.067*
C6	0.5018 (3)	0.1405 (2)	0.1514 (3)	0.0485 (7)
H6A	0.5384	0.1363	0.2506	0.058*
H6B	0.4460	0.0751	0.1152	0.058*
C7	0.3195 (3)	0.2542 (2)	0.1453 (3)	0.0471 (6)
C8	0.7822 (2)	0.2371 (2)	0.2978 (3)	0.0442 (6)
N1	0.0308 (3)	−0.0636 (2)	0.3628 (3)	0.0590 (7)
H1	0.041 (4)	−0.115 (2)	0.421 (3)	0.088*
O5	0.01175 (16)	0.18473 (15)	0.09311 (18)	0.0470 (5)
C9	0.0146 (2)	0.1065 (2)	0.1791 (2)	0.0384 (6)
C10	−0.0764 (3)	0.0194 (2)	0.1462 (3)	0.0495 (7)
H10	−0.1444	0.0185	0.0603	0.059*
C11	−0.0659 (3)	−0.0638 (2)	0.2390 (4)	0.0609 (8)
H11	−0.1266	−0.1213	0.2159	0.073*
C12	0.1179 (3)	0.0179 (3)	0.4004 (3)	0.0584 (8)
H12	0.1836	0.0165	0.4880	0.070*
C13	0.1124 (3)	0.1029 (2)	0.3127 (3)	0.0497 (7)
H13	0.1740	0.1599	0.3410	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0561 (13)	0.0868 (16)	0.0593 (13)	−0.0227 (12)	0.0280 (11)	−0.0188 (12)
O2	0.0729 (16)	0.130 (2)	0.0779 (16)	−0.0249 (15)	0.0433 (14)	−0.0510 (16)
O3	0.0722 (15)	0.0658 (14)	0.0532 (13)	−0.0221 (12)	−0.0005 (11)	0.0129 (11)
O4	0.1024 (19)	0.0580 (14)	0.0471 (12)	−0.0139 (13)	−0.0003 (12)	0.0119 (11)
C1	0.0442 (14)	0.0476 (15)	0.0296 (12)	−0.0022 (11)	0.0115 (11)	0.0003 (11)
C2	0.0532 (16)	0.0370 (14)	0.0506 (15)	0.0012 (12)	0.0166 (13)	0.0067 (12)
C3	0.0529 (16)	0.0624 (18)	0.0448 (15)	−0.0094 (14)	0.0146 (13)	0.0164 (13)
C4	0.0479 (15)	0.0695 (19)	0.0349 (13)	0.0017 (14)	0.0207 (12)	0.0011 (13)
C5	0.0569 (17)	0.0591 (18)	0.0447 (15)	0.0045 (14)	0.0157 (13)	−0.0176 (13)
C6	0.0550 (16)	0.0374 (14)	0.0483 (15)	−0.0063 (12)	0.0175 (13)	−0.0069 (12)
C7	0.0480 (15)	0.0490 (16)	0.0400 (14)	−0.0005 (12)	0.0146 (12)	0.0019 (12)
C8	0.0437 (14)	0.0500 (16)	0.0386 (13)	0.0008 (12)	0.0174 (11)	0.0004 (12)
N1	0.0757 (18)	0.0480 (15)	0.0647 (17)	0.0093 (13)	0.0411 (15)	0.0138 (12)
O5	0.0441 (10)	0.0454 (10)	0.0432 (10)	−0.0014 (8)	0.0109 (8)	0.0082 (8)
C9	0.0411 (13)	0.0345 (13)	0.0403 (13)	0.0048 (10)	0.0182 (11)	−0.0015 (10)
C10	0.0450 (15)	0.0467 (16)	0.0554 (16)	−0.0027 (12)	0.0202 (13)	−0.0062 (13)
C11	0.0667 (19)	0.0407 (16)	0.088 (2)	−0.0111 (14)	0.0458 (19)	−0.0066 (15)
C12	0.0672 (19)	0.0558 (18)	0.0488 (16)	0.0103 (16)	0.0217 (14)	0.0081 (14)
C13	0.0517 (15)	0.0439 (15)	0.0449 (14)	−0.0043 (12)	0.0125 (12)	−0.0001 (12)

Geometric parameters (Å, º) top

O1—C7	1.310 (3)	C4—H4	0.9800
O1—H1'	0.8400 (10)	C5—C6	1.516 (4)
O2—C7	1.201 (3)	C5—H5A	0.9700
O3—C8	1.299 (3)	C5—H5B	0.9700
O3—H3'	0.8400 (11)	C6—H6A	0.9700
O4—C8	1.189 (3)	C6—H6B	0.9700
C1—C7	1.498 (4)	N1—C12	1.324 (4)
C1—C2	1.518 (4)	N1—C11	1.333 (4)
C1—C6	1.534 (4)	N1—H1	0.8400 (10)
C1—H1A	0.9800	O5—C9	1.289 (3)
C2—C3	1.518 (4)	C9—C10	1.403 (4)
C2—H2A	0.9700	C9—C13	1.408 (4)
C2—H2B	0.9700	C10—C11	1.359 (4)
C3—C4	1.524 (4)	C10—H10	0.9300
C3—H3A	0.9700	C11—H11	0.9300
C3—H3B	0.9700	C12—C13	1.351 (4)
C4—C8	1.517 (4)	C12—H12	0.9300
C4—C5	1.525 (4)	C13—H13	0.9300

C7—O1—H1'	112 (3)	H5A—C5—H5B	107.8
C8—O3—H3'	110 (3)	C5—C6—C1	111.2 (2)
C7—C1—C2	113.0 (2)	C5—C6—H6A	109.4
C7—C1—C6	110.6 (2)	C1—C6—H6A	109.4
C2—C1—C6	109.8 (2)	C5—C6—H6B	109.4
C7—C1—H1A	107.7	C1—C6—H6B	109.4
C2—C1—H1A	107.7	H6A—C6—H6B	108.0
C6—C1—H1A	107.7	O2—C7—O1	122.0 (3)
C3—C2—C1	110.7 (2)	O2—C7—C1	125.7 (3)
C3—C2—H2A	109.5	O1—C7—C1	112.3 (2)
C1—C2—H2A	109.5	O4—C8—O3	122.4 (2)
C3—C2—H2B	109.5	O4—C8—C4	124.3 (3)
C1—C2—H2B	109.5	O3—C8—C4	113.3 (2)
H2A—C2—H2B	108.1	C12—N1—C11	121.6 (3)
C2—C3—C4	112.4 (2)	C12—N1—H1	116 (3)
C2—C3—H3A	109.1	C11—N1—H1	122 (3)
C4—C3—H3A	109.1	O5—C9—C10	123.0 (2)
C2—C3—H3B	109.1	O5—C9—C13	121.1 (2)
C4—C3—H3B	109.1	C10—C9—C13	115.8 (2)
H3A—C3—H3B	107.9	C11—C10—C9	120.6 (3)
C8—C4—C3	112.5 (2)	C11—C10—H10	119.7
C8—C4—C5	112.2 (2)	C9—C10—H10	119.7
C3—C4—C5	111.2 (2)	N1—C11—C10	120.5 (3)
C8—C4—H4	106.8	N1—C11—H11	119.8
C3—C4—H4	106.8	C10—C11—H11	119.8
C5—C4—H4	106.8	N1—C12—C13	120.6 (3)
C6—C5—C4	112.6 (2)	N1—C12—H12	119.7
C6—C5—H5A	109.1	C13—C12—H12	119.7
C4—C5—H5A	109.1	C12—C13—C9	120.9 (3)
C6—C5—H5B	109.1	C12—C13—H13	119.6
C4—C5—H5B	109.1	C9—C13—H13	119.6

C7—C1—C2—C3	−177.7 (2)	C6—C1—C7—O1	−79.7 (3)
C6—C1—C2—C3	58.2 (3)	C3—C4—C8—O4	136.9 (3)
C1—C2—C3—C4	−56.6 (3)	C5—C4—C8—O4	10.5 (4)
C2—C3—C4—C8	−74.5 (3)	C3—C4—C8—O3	−44.6 (3)
C2—C3—C4—C5	52.4 (3)	C5—C4—C8—O3	−170.9 (2)
C8—C4—C5—C6	75.7 (3)	O5—C9—C10—C11	177.2 (2)
C3—C4—C5—C6	−51.4 (3)	C13—C9—C10—C11	−1.8 (4)
C4—C5—C6—C1	54.4 (3)	C12—N1—C11—C10	1.2 (4)
C7—C1—C6—C5	177.2 (2)	C9—C10—C11—N1	0.3 (4)
C2—C1—C6—C5	−57.4 (3)	C11—N1—C12—C13	−1.1 (5)
C2—C1—C7—O2	−22.5 (4)	N1—C12—C13—C9	−0.5 (4)
C6—C1—C7—O2	101.1 (3)	O5—C9—C13—C12	−177.1 (3)
C2—C1—C7—O1	156.7 (2)	C10—C9—C13—C12	1.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1′···O5	0.84	1.82	2.638 (3)	165
O3—H3′···O5ⁱ	0.84	1.76	2.594 (2)	175
N1—H1···O4ⁱⁱ	0.84	2.29	2.921 (3)	132
N1—H1···O5ⁱⁱⁱ	0.84	2.39	3.038 (3)	134
C1—H1A···O2^iv	0.98	2.67	3.625 (4)	162
C11—H11···O2ⁱⁱⁱ	0.93	2.62	3.420 (5)	143
C12—H12···O4ⁱⁱ	0.93	2.47	3.014 (4)	117

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

Experimental details

Crystal data
Chemical formula	C₅H₅NO·C₈H₁₂O₄
M_r	267.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.749 (2), 11.618 (2), 10.8010 (19)
β (°)	115.383 (2)
V (Å³)	1332.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.50 × 0.43 × 0.24

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.95, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	12552, 2345, 2229
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.161, 1.02
No. of reflections	2345
No. of parameters	181
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.27

Computer programs: SMART (Bruker, 2000), SAINT-Plus-NT (Bruker, 2001), SHELXTL-NT (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
O1—H1'···O5	0.84	1.82	2.638 (3)	165
O3—H3'···O5ⁱ	0.84	1.76	2.594 (2)	175
N1—H1···O4ⁱⁱ	0.84	2.29	2.921 (3)	132
N1—H1···O5ⁱⁱⁱ	0.84	2.39	3.038 (3)	134
C1—H1A···O2^iv	0.98	2.67	3.625 (4)	162
C11—H11···O2ⁱⁱⁱ	0.93	2.62	3.420 (5)	143
C12—H12···O4ⁱⁱ	0.93	2.47	3.014 (4)	117

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

Acknowledgements

This work was supported financially by the Universidad Autónoma de Sinaloa (PROFAPI 2012/049).

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