4-[(E)-2-(Pyridin-2-yl)ethen­yl]pyridine–terephthalic acid (2/1)

Castro-Montes, P.; Guerrero-Alvarez, J.A.; Hopfl, H.; Campos-Gaxiola, J.J.; Cruz-Enriquez, A.

doi:10.1107/S1600536812046284

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3383-o3384

doi:10.1107/S1600536812046284

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4-[(E)-2-(Pyridin-2-yl)ethenyl]pyridine–terephthalic acid (2/1)

Paola Castro-Montes,^a Jorge A. Guerrero-Alvarez,^b Herbert Hopfl,^b Jose J. Campos-Gaxiola ^a and Adriana Cruz-Enriquez ^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, and ^bCentro de Investigaciones Quimicas, Universidad Autonoma del Estado de Morelos, Av. Universidad 1001, CP 62210, Cuernavaca, Morelos, Mexico
^*Correspondence e-mail: cenriqueza@yahoo.com.mx

(Received 5 November 2012; accepted 8 November 2012; online 17 November 2012)

The title 2:1 co-crystal, 2C₁₂H₁₀N₂·C₈H₆O₄, crystallizes with one molecule of 4-[(E)-2-(pyridin-2-yl)ethenyl]pyridine (A) and one half-molecule of terephthalic acid (B) in the asymmetric unit. In the crystal, the components are linked through heterodimeric COOH⋯N_pyridine synthons, forming linear aggregates of composition –A–B–A–B–. Further linkage through weak C—H⋯O and C—H⋯π interactions gives two-dimensional hydrogen-bonded undulating sheets propagating in the [100] and [010] directions. These layers are connected through additional weak C—H⋯O contacts, forming a three-dimensional structure.

Related literature

For reports on supramolecular crystal engineering and potential applications of co-crystals, see: Desiraju (1995 ); Simon & Bassoul (2000 ); Bhogala & Nangia (2003 ); Weyna et al. (2009 ); Yan et al. (2012 ). For background to related co-crystals, see: Santra et al. (2008 ); Moon & Park (2012 ); Ebenezer & Muthiah (2012 ).

Experimental

Crystal data

C₁₂H₁₀N₂·0.5C₈H₆O₄
M_r = 265.28
Monoclinic, P 2₁ /n
a = 6.3821 (8) Å
b = 32.301 (4) Å
c = 6.8721 (8) Å
β = 111.440 (2)°
V = 1318.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.48 × 0.41 × 0.34 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.96, T_max = 0.97
12715 measured reflections
2328 independent reflections
2119 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.149
S = 1.17
2328 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N2/C12–C16 pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1′⋯N1ⁱ	0.84	1.77	2.604 (2)	177
C9—H9⋯O2ⁱⁱ	0.93	2.67	3.285 (3)	125
C13—H13⋯O2ⁱⁱⁱ	0.93	2.52	3.396 (2)	157
C5—H5⋯O2^iv	0.93	2.64	3.135 (2)	114
C16—H16⋯Cg^v	0.93	2.86	3.627 (3)	141
Symmetry codes: (i) x, y, z+1; (ii) x, y, z-1; (iii) x-1, y, z; (iv) x-1, y, z-1; (v) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus (Bruker 2001 ); data reduction: SAINT-Plus; 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, global. DOI: 10.1107/S1600536812046284/su2525sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812046284/su2525Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812046284/su2525Isup3.cml

checkCIF report

Comment top

Supramolecular crystal engineering has attracted growing interest over the past few decades because of its importance in biological systems, molecular recognition (Simon et al., 2000), 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 molecules (Bhogala & Nangia, 2003; Santra et al., 2008; Moon & Park, 2012; Ebenezer & Muthiah, 2012). Herein, we report on the solid-state structure of a 2:1 co-crystal formed between an asymmetric bipyridine [4-((E)-2-(pyridin-2-yl)ethenyl)pyridine] and a symmetric dicarboxylic acid [terephthalic acid].

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit contains one molecule of 4-((E)-2-(pyridin-2-yl)ethenyl)pyridine and half a molecule of terephthalic acid located on a crystallographic inversion center. Both components have almost planar molecular structures as seen from the C10—C11—C12—N2 torsion angle of -4.2 (3)° for the bipyridine molecule and the O1—C4—C1—C2 torsion angle of -6.0 (3)° for the terephthalic acid.

In the crystal lattice, each terephthalic acid is linked to two bipyridine molecules through intermolecular O—H···N and C—H···O interactions giving the well known heterodimeric COOH···N_pyridine synthon. The so formed linear aggregates are connected through additional weak C—H···O contacts to generate tapes parallel to the (1–41) series of planes, which through C—H···π contacts generate undulating two-dimensional supramolecular layers (Fig. 2 and Table 1). In the third dimension, these layers are interconnected through additional weak C—H···O contacts. Interestingly, the 2-pyridine nitrogen atom is not involved in short intermolecular hydrogen bonding interactions.

Related literature top

For reports on supramolecular crystal engineering and potential applications of co-crystals, see: Desiraju (1995); Simon & Bassoul (2000); Bhogala & Nangia (2003); Weyna et al. (2009); Yan et al. (2012). For background to related co-crystals, see: Santra et al. (2008); Moon & Park (2012); Ebenezer & Muthiah (2012).

Experimental top

0.200 g (1.10 mmol) of 4-((E)-2-(pyridin-2-yl)ethenyl)pyridine and 0.180 g (1.10 mmol) of terephthalic acid were ground in a mortar for 20 min after adding 3 drops of CH₃OH. The resulting powder was then dissolved in 10 ml of CH₃OH and kept for crystallization by slow evaporation of the solvent at ambient conditions to give colourless block-like crystals, suitable for single-crystal X-ray diffraction analysis, after one week. Spectroscopic and TGA data for the title compound are available in the archived CIF.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker 2001); data reduction: SAINT-Plus (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 structures of the components in the title compound, showing the atom numbering. Displacement ellipsoids are drawn at the 50% probability level. [symmetry code: (i) -x + 2, -y, -z + 1].
	Fig. 2. View of the two-dimensional supramolecular layer formed through O—H···N, C—H···O and C—H···π interactions (dashed lines; see Table 1 for details), in the crystal structure of the title compound.

4-[(E)-2-(Pyridin-2-yl)ethenyl]pyridine–terephthalic acid (2/1) top

Crystal data top

C₁₂H₁₀N₂·0.5C₈H₆O₄	F(000) = 556
M_r = 265.28	D_x = 1.336 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4971 reflections
a = 6.3821 (8) Å	θ = 2.5–27.1°
b = 32.301 (4) Å	µ = 0.09 mm⁻¹
c = 6.8721 (8) Å	T = 293 K
β = 111.440 (2)°	Block, colourless
V = 1318.6 (3) Å³	0.48 × 0.41 × 0.34 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2328 independent reflections
Radiation source: fine-focus sealed tube	2119 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.96, T_max = 0.97	k = −38→38
12715 measured reflections	l = −8→8

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ²(F_o²) + (0.0769P)² + 0.2452P] where P = (F_o² + 2F_c²)/3
2328 reflections	(Δ/σ)_max < 0.001
184 parameters	Δρ_max = 0.14 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₂H₁₀N₂·0.5C₈H₆O₄	V = 1318.6 (3) Å³
M_r = 265.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.3821 (8) Å	µ = 0.09 mm⁻¹
b = 32.301 (4) Å	T = 293 K
c = 6.8721 (8) Å	0.48 × 0.41 × 0.34 mm
β = 111.440 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2328 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2119 reflections with I > 2σ(I)
T_min = 0.96, T_max = 0.97	R_int = 0.033
12715 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	1 restraint
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	Δρ_max = 0.14 e Å⁻³
2328 reflections	Δρ_min = −0.20 e Å⁻³
184 parameters

Special details top

Experimental. Spectroscopic and TGA data for the title compound:

IR (KBr): 3056, 2944, 1706, 1683, 1606, 1581, 1504, 1425, 1290 y 731 cm^-1. ¹H-RMN (200 MHz, DMSO-d₆, TMS): δ 8.59 (m, 3H), 8.04 (s, 4H), 7.83 (td, J = 0.8, 4 Hz, 1H), 7.61 (m, 5H), 7.32 (m, 1H). TGA Calcd. for 2 C₁₂H₁₀N₂: 68.69. Found: 69.27% (303 - 533 K).

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	0.7604 (3)	0.03567 (5)	0.8732 (2)	0.0626 (4)
H1'	0.752 (4)	0.0508 (7)	0.969 (3)	0.094*
O2	1.0571 (2)	0.07552 (4)	0.9137 (2)	0.0646 (4)
C1	0.9678 (3)	0.02216 (5)	0.6602 (3)	0.0419 (4)
C2	0.8138 (3)	−0.00755 (6)	0.5490 (3)	0.0497 (5)
H2	0.6876	−0.0128	0.5824	0.060*
C3	1.1549 (3)	0.02934 (6)	0.6094 (3)	0.0502 (5)
H3	1.2603	0.0491	0.6830	0.060*
C4	0.9339 (3)	0.04711 (6)	0.8289 (3)	0.0478 (5)
N1	0.7178 (3)	0.08162 (5)	0.1678 (2)	0.0525 (4)
N2	0.6102 (3)	0.20912 (5)	0.9682 (3)	0.0577 (5)
C5	0.5534 (3)	0.07399 (6)	0.2373 (3)	0.0525 (5)
H5	0.4559	0.0521	0.1784	0.063*
C6	0.5203 (3)	0.09677 (6)	0.3915 (3)	0.0515 (5)
H6	0.4020	0.0903	0.4346	0.062*
C7	0.6625 (3)	0.12946 (6)	0.4837 (3)	0.0471 (5)
C8	0.8332 (3)	0.13732 (7)	0.4096 (3)	0.0567 (5)
H8	0.9330	0.1590	0.4651	0.068*
C9	0.8553 (4)	0.11300 (7)	0.2539 (3)	0.0580 (5)
H9	0.9714	0.1188	0.2067	0.070*
C10	0.6360 (3)	0.15554 (6)	0.6476 (3)	0.0519 (5)
H10	0.7328	0.1781	0.6911	0.062*
C11	0.4900 (3)	0.15052 (6)	0.7397 (3)	0.0509 (5)
H11	0.3948	0.1277	0.6996	0.061*
C12	0.4641 (3)	0.17767 (5)	0.8998 (3)	0.0472 (5)
C13	0.2917 (3)	0.17128 (6)	0.9726 (3)	0.0545 (5)
H13	0.1941	0.1490	0.9238	0.065*
C14	0.2652 (4)	0.19789 (7)	1.1171 (3)	0.0628 (6)
H14	0.1481	0.1942	1.1654	0.075*
C15	0.4136 (4)	0.22994 (7)	1.1891 (3)	0.0656 (6)
H15	0.4008	0.2484	1.2880	0.079*
C16	0.5813 (4)	0.23397 (7)	1.1110 (4)	0.0682 (6)
H16	0.6827	0.2557	1.1613	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0692 (9)	0.0688 (10)	0.0642 (9)	−0.0138 (7)	0.0414 (8)	−0.0204 (7)
O2	0.0679 (9)	0.0625 (9)	0.0677 (9)	−0.0156 (7)	0.0300 (8)	−0.0246 (7)
C1	0.0449 (10)	0.0379 (9)	0.0434 (10)	0.0019 (7)	0.0166 (8)	0.0039 (7)
C2	0.0455 (10)	0.0521 (11)	0.0588 (11)	−0.0072 (8)	0.0276 (9)	−0.0060 (9)
C3	0.0508 (11)	0.0474 (10)	0.0553 (11)	−0.0111 (8)	0.0228 (9)	−0.0094 (8)
C4	0.0498 (10)	0.0485 (11)	0.0452 (10)	0.0027 (8)	0.0174 (8)	0.0011 (8)
N1	0.0618 (10)	0.0534 (9)	0.0457 (9)	0.0075 (8)	0.0237 (8)	0.0007 (7)
N2	0.0646 (11)	0.0492 (9)	0.0602 (10)	−0.0050 (8)	0.0238 (8)	−0.0120 (8)
C5	0.0594 (12)	0.0499 (11)	0.0494 (11)	−0.0002 (9)	0.0215 (9)	−0.0047 (8)
C6	0.0560 (11)	0.0508 (11)	0.0521 (11)	−0.0006 (9)	0.0250 (9)	−0.0039 (8)
C7	0.0525 (11)	0.0440 (10)	0.0443 (10)	0.0072 (8)	0.0170 (8)	0.0036 (8)
C8	0.0592 (12)	0.0568 (12)	0.0559 (11)	−0.0050 (9)	0.0232 (10)	−0.0035 (9)
C9	0.0620 (12)	0.0632 (13)	0.0576 (12)	0.0011 (10)	0.0323 (10)	0.0025 (10)
C10	0.0596 (11)	0.0439 (10)	0.0522 (11)	−0.0025 (8)	0.0205 (9)	−0.0047 (8)
C11	0.0594 (11)	0.0433 (10)	0.0499 (11)	−0.0015 (9)	0.0199 (9)	−0.0059 (8)
C12	0.0555 (11)	0.0399 (10)	0.0439 (10)	0.0051 (8)	0.0154 (8)	0.0020 (7)
C13	0.0643 (12)	0.0461 (11)	0.0548 (11)	0.0005 (9)	0.0239 (10)	0.0014 (8)
C14	0.0770 (14)	0.0600 (13)	0.0610 (12)	0.0113 (11)	0.0367 (11)	0.0038 (10)
C15	0.0885 (16)	0.0541 (12)	0.0562 (12)	0.0142 (11)	0.0288 (11)	−0.0072 (10)
C16	0.0810 (15)	0.0527 (12)	0.0669 (13)	−0.0062 (11)	0.0224 (12)	−0.0188 (10)

Geometric parameters (Å, º) top

O1—C4	1.305 (2)	C7—C8	1.384 (3)
O1—H1'	0.8401 (10)	C7—C10	1.465 (3)
O2—C4	1.210 (2)	C8—C9	1.376 (3)
C1—C3	1.381 (2)	C8—H8	0.9300
C1—C2	1.386 (3)	C9—H9	0.9300
C1—C4	1.491 (3)	C10—C11	1.314 (3)
C2—C3ⁱ	1.371 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.463 (3)
C3—C2ⁱ	1.371 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.380 (3)
N1—C5	1.325 (2)	C13—C14	1.369 (3)
N1—C9	1.330 (3)	C13—H13	0.9300
N2—C16	1.332 (3)	C14—C15	1.368 (3)
N2—C12	1.342 (2)	C14—H14	0.9300
C5—C6	1.369 (3)	C15—C16	1.368 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.386 (3)	C16—H16	0.9300
C6—H6	0.9300

C4—O1—H1'	108.9 (19)	C7—C8—H8	120.0
C3—C1—C2	118.76 (17)	N1—C9—C8	122.86 (19)
C3—C1—C4	119.37 (16)	N1—C9—H9	118.6
C2—C1—C4	121.86 (16)	C8—C9—H9	118.6
C3ⁱ—C2—C1	120.91 (17)	C11—C10—C7	126.94 (18)
C3ⁱ—C2—H2	119.5	C11—C10—H10	116.5
C1—C2—H2	119.5	C7—C10—H10	116.5
C2ⁱ—C3—C1	120.33 (17)	C10—C11—C12	125.68 (18)
C2ⁱ—C3—H3	119.8	C10—C11—H11	117.2
C1—C3—H3	119.8	C12—C11—H11	117.2
O2—C4—O1	124.02 (17)	N2—C12—C13	122.00 (17)
O2—C4—C1	122.08 (17)	N2—C12—C11	117.51 (17)
O1—C4—C1	113.89 (16)	C13—C12—C11	120.47 (17)
C5—N1—C9	117.55 (16)	C14—C13—C12	119.7 (2)
C16—N2—C12	116.65 (18)	C14—C13—H13	120.2
N1—C5—C6	123.07 (18)	C12—C13—H13	120.2
N1—C5—H5	118.5	C15—C14—C13	119.0 (2)
C6—C5—H5	118.5	C15—C14—H14	120.5
C5—C6—C7	120.20 (18)	C13—C14—H14	120.5
C5—C6—H6	119.9	C14—C15—C16	117.86 (19)
C7—C6—H6	119.9	C14—C15—H15	121.1
C8—C7—C6	116.35 (17)	C16—C15—H15	121.1
C8—C7—C10	120.33 (18)	N2—C16—C15	124.8 (2)
C6—C7—C10	123.31 (17)	N2—C16—H16	117.6
C9—C8—C7	119.96 (19)	C15—C16—H16	117.6
C9—C8—H8	120.0

C3—C1—C2—C3ⁱ	−0.4 (3)	C7—C8—C9—N1	0.2 (3)
C4—C1—C2—C3ⁱ	178.17 (17)	C8—C7—C10—C11	−176.30 (19)
C2—C1—C3—C2ⁱ	0.4 (3)	C6—C7—C10—C11	5.1 (3)
C4—C1—C3—C2ⁱ	−178.21 (17)	C7—C10—C11—C12	−178.50 (17)
C3—C1—C4—O2	5.2 (3)	C16—N2—C12—C13	0.2 (3)
C2—C1—C4—O2	−173.37 (18)	C16—N2—C12—C11	178.75 (18)
C3—C1—C4—O1	−175.43 (17)	C10—C11—C12—N2	−4.2 (3)
C2—C1—C4—O1	6.0 (3)	C10—C11—C12—C13	174.40 (19)
C9—N1—C5—C6	0.0 (3)	N2—C12—C13—C14	0.8 (3)
N1—C5—C6—C7	−0.3 (3)	C11—C12—C13—C14	−177.69 (18)
C5—C6—C7—C8	0.5 (3)	C12—C13—C14—C15	−1.2 (3)
C5—C6—C7—C10	179.21 (18)	C13—C14—C15—C16	0.5 (3)
C6—C7—C8—C9	−0.5 (3)	C12—N2—C16—C15	−0.9 (3)
C10—C7—C8—C9	−179.21 (18)	C14—C15—C16—N2	0.6 (4)
C5—N1—C9—C8	0.1 (3)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N2/C12–C16 pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1′···N1ⁱⁱ	0.84	1.77	2.604 (2)	177
C9—H9···O2ⁱⁱⁱ	0.93	2.67	3.285 (3)	125
C13—H13···O2^iv	0.93	2.52	3.396 (2)	157
C5—H5···O2^v	0.93	2.64	3.135 (2)	114
C16—H16···Cg^vi	0.93	2.86	3.627 (3)	141

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₂·0.5C₈H₆O₄
M_r	265.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	6.3821 (8), 32.301 (4), 6.8721 (8)
β (°)	111.440 (2)
V (Å³)	1318.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.41 × 0.34

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.96, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	12715, 2328, 2119
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.149, 1.17
No. of reflections	2328
No. of parameters	184
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.20

Computer programs: SMART (Bruker, 2000), SAINT-Plus (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

Cg is the centroid of the N2/C12–C16 pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1'···N1ⁱ	0.84	1.77	2.604 (2)	177
C9—H9···O2ⁱⁱ	0.93	2.67	3.285 (3)	125
C13—H13···O2ⁱⁱⁱ	0.93	2.52	3.396 (2)	157
C5—H5···O2^iv	0.93	2.64	3.135 (2)	114
C16—H16···Cg^v	0.93	2.86	3.627 (3)	141

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

Acknowledgements

This work was supported financially by the Universidad Autónoma de Sinaloa (PROFAPI 2011/048). PCM thanks the Consejo Nacional de Ciencia y Tecnologia (CONACYT) for support in the form of a scholarship.

References

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Volume 68| Part 12| December 2012| Pages o3383-o3384

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