1-(2,3-Di­cyano­phen­yl)pyridin-1-ium-4-olate monohydrate

Han, Z.; Zhu, Y.; Tian, X.; Feng, S.

doi:10.1107/S1600536813008891

organic compounds

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Volume 69| Part 5| May 2013| Page o767

https://doi.org/10.1107/S1600536813008891

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1-(2,3-Dicyanophenyl)pyridin-1-ium-4-olate monohydrate

Zhe Han,^a,^b Ying Zhu,^b Xuelei Tian ^a and Suping Feng ^c ^*

^aSchool of Materials Science and Engineering of Shandong University, 250014 Jinan, People's Republic of China, ^bNew Materials Institute of Shandong Academy of Sciences, 250014 Jinan, People's Republic of China, and ^cSchool of Environmental Science and Engineering of Shandong University, 250100 Jinan, People's Republic of China
^*Correspondence e-mail: fengsuping@126.com

(Received 5 November 2012; accepted 2 April 2013; online 20 April 2013)

In the crystal structure of the title compound, C₁₃H₇N₃O·H₂O, the components are associated into chains along [010] through strong O—H⋯O hydrogen bonds with the free water molecules as bridging ligands. These chains are further cross-linked by C—H⋯O and C—H⋯N hydrogen bonds, forming a three-dimensional structure.

Related literature

For the preparation of the title compound, see: Archibald et al. (1994 )

Experimental

Crystal data

C₁₃H₇N₃O·H₂O
M_r = 239.23
Monoclinic, P 2₁ /c
a = 11.977 (2) Å
b = 7.2497 (12) Å
c = 13.850 (2) Å
β = 94.244 (3)°
V = 1199.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.989, T_max = 0.993
5795 measured reflections
2112 independent reflections
1349 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.124
S = 1.03
2112 reflections
172 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O1	0.98 (3)	1.79 (3)	2.763 (2)	170 (3)
O1W—H1WB⋯O1ⁱ	0.87 (3)	1.88 (3)	2.721 (2)	162 (3)
C6—H6A⋯O1Wⁱⁱ	0.93	2.37	3.302 (3)	177
C13—H13A⋯O1Wⁱⁱⁱ	0.93	2.38	3.311 (3)	175
C9—H9A⋯N1^iv	0.93	2.55	3.440 (2)	160
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1; (iv) x, y+1, z.

Data collection: APEX2 (Bruker, 2004 ); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813008891/bv2216sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813008891/bv2216Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813008891/bv2216Isup3.cml

checkCIF report

Comment top

In the crystal structure of the title compound, (C₁₃H₇N₃O)(H₂O), the units are associated into a chain through strong O—H···O hydrogen bonds with the free water molecules as the bridging ligands. These chains are further crosslinked by C-H···O interactions. In addition there are weak pairwise C—H···N hydrogen bonds.

Related literature top

For the preparation of the title compound, see: Archibald et al. (1994)

Experimental top

The preparation of the title compound, see, Archibald et al. (1994)

Structure description top

For the preparation of the title compound, see: Archibald et al. (1994)

Computing details top

Data collection: APEX2 (Bruker, 2004); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level; H atoms are given as spheres of arbitrary radius.
	Fig. 2. The packing diagram of the title compound with hydrogen bonds shown as dashed lines.

1-(2,3-Dicyanophenyl)pyridin-1-ium-4-olate monohydrate top

Crystal data top

C₁₃H₇N₃O·H₂O	F(000) = 496
M_r = 239.23	D_x = 1.325 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2117 reflections
a = 11.977 (2) Å	θ = 1.7–25.0°
b = 7.2497 (12) Å	µ = 0.09 mm⁻¹
c = 13.850 (2) Å	T = 293 K
β = 94.244 (3)°	Block, colorless
V = 1199.3 (3) Å³	0.12 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2112 independent reflections
Radiation source: fine-focus sealed tube	1349 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→14
T_min = 0.989, T_max = 0.993	k = 0→8
5795 measured reflections	l = 0→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0572P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2112 reflections	Δρ_max = 0.12 e Å⁻³
172 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (4)

Crystal data top

C₁₃H₇N₃O·H₂O	V = 1199.3 (3) Å³
M_r = 239.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.977 (2) Å	µ = 0.09 mm⁻¹
b = 7.2497 (12) Å	T = 293 K
c = 13.850 (2) Å	0.12 × 0.10 × 0.08 mm
β = 94.244 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2112 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1349 reflections with I > 2σ(I)
T_min = 0.989, T_max = 0.993	R_int = 0.042
5795 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.12 e Å⁻³
2112 reflections	Δρ_min = −0.14 e Å⁻³
172 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.44687 (15)	0.4052 (2)	0.64729 (11)	0.0821 (6)
N1	0.14211 (16)	−0.0800 (2)	0.38040 (14)	0.0686 (6)
N2	0.00645 (18)	−0.1230 (3)	0.11391 (13)	0.0794 (7)
N3	0.29064 (13)	0.35472 (19)	0.37786 (11)	0.0477 (5)
C1	0.23465 (16)	0.3377 (2)	0.28309 (13)	0.0469 (5)
C2	0.17290 (15)	0.1798 (2)	0.25806 (13)	0.0437 (5)
C3	0.11900 (16)	0.1688 (2)	0.16464 (14)	0.0479 (5)
C4	0.12482 (18)	0.3119 (3)	0.09995 (14)	0.0578 (6)
H4A	0.0889	0.3032	0.0383	0.069*
C5	0.1844 (2)	0.4680 (3)	0.12749 (15)	0.0652 (7)
H5A	0.1875	0.5659	0.0844	0.078*
C6	0.23959 (19)	0.4810 (3)	0.21802 (16)	0.0609 (6)
H6A	0.2803	0.5867	0.2354	0.073*
C7	0.15735 (17)	0.0352 (3)	0.32680 (15)	0.0482 (5)
C8	0.05625 (18)	0.0052 (3)	0.13666 (14)	0.0561 (6)
C9	0.27488 (17)	0.5072 (2)	0.43253 (15)	0.0536 (6)
H9A	0.2273	0.5997	0.4075	0.064*
C10	0.32575 (18)	0.5283 (3)	0.52132 (15)	0.0567 (6)
H10A	0.3128	0.6349	0.5561	0.068*
C11	0.39919 (18)	0.3909 (3)	0.56354 (15)	0.0578 (6)
C12	0.41474 (18)	0.2360 (3)	0.50307 (15)	0.0618 (6)
H12A	0.4627	0.1421	0.5257	0.074*
C13	0.36240 (17)	0.2209 (3)	0.41422 (14)	0.0570 (6)
H13A	0.3752	0.1176	0.3768	0.068*
O1W	0.60702 (15)	0.1549 (2)	0.71708 (14)	0.0732 (5)
H1WA	0.544 (2)	0.236 (4)	0.6961 (19)	0.121 (11)*
H1WB	0.583 (2)	0.095 (4)	0.766 (2)	0.120 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1059 (14)	0.0738 (11)	0.0615 (10)	0.0203 (9)	−0.0291 (9)	−0.0165 (8)
N1	0.0756 (14)	0.0545 (11)	0.0750 (14)	−0.0007 (9)	0.0007 (11)	0.0099 (10)
N2	0.0927 (16)	0.0754 (13)	0.0685 (14)	−0.0333 (12)	−0.0050 (11)	−0.0101 (10)
N3	0.0482 (10)	0.0384 (9)	0.0549 (10)	0.0008 (7)	−0.0071 (8)	−0.0087 (7)
C1	0.0472 (12)	0.0433 (11)	0.0494 (12)	−0.0008 (9)	−0.0022 (9)	−0.0062 (9)
C2	0.0458 (12)	0.0385 (10)	0.0467 (11)	−0.0013 (8)	0.0019 (9)	−0.0029 (8)
C3	0.0481 (12)	0.0464 (11)	0.0492 (12)	−0.0050 (9)	0.0033 (9)	−0.0060 (9)
C4	0.0663 (15)	0.0606 (13)	0.0452 (12)	−0.0070 (11)	−0.0046 (10)	−0.0017 (10)
C5	0.0849 (17)	0.0540 (13)	0.0557 (14)	−0.0102 (12)	−0.0026 (12)	0.0070 (10)
C6	0.0718 (16)	0.0459 (12)	0.0637 (15)	−0.0143 (11)	−0.0042 (12)	−0.0005 (10)
C7	0.0487 (13)	0.0419 (11)	0.0531 (13)	−0.0006 (9)	−0.0016 (10)	−0.0078 (10)
C8	0.0590 (14)	0.0586 (13)	0.0497 (13)	−0.0132 (11)	−0.0019 (10)	−0.0053 (10)
C9	0.0571 (14)	0.0377 (11)	0.0640 (14)	0.0032 (9)	−0.0082 (11)	−0.0077 (9)
C10	0.0642 (14)	0.0435 (11)	0.0608 (14)	0.0065 (10)	−0.0062 (11)	−0.0141 (9)
C11	0.0654 (15)	0.0504 (12)	0.0555 (14)	0.0030 (11)	−0.0088 (11)	−0.0090 (10)
C12	0.0653 (16)	0.0503 (12)	0.0667 (15)	0.0159 (10)	−0.0148 (11)	−0.0088 (10)
C13	0.0585 (14)	0.0434 (11)	0.0673 (14)	0.0088 (10)	−0.0082 (11)	−0.0128 (10)
O1W	0.0750 (13)	0.0633 (11)	0.0813 (13)	0.0009 (9)	0.0063 (10)	0.0050 (9)

Geometric parameters (Å, º) top

O1—C11	1.259 (2)	C5—C6	1.376 (3)
N1—C7	1.141 (2)	C5—H5A	0.9300
N2—C8	1.136 (2)	C6—H6A	0.9300
N3—C9	1.361 (2)	C9—C10	1.340 (3)
N3—C13	1.367 (2)	C9—H9A	0.9300
N3—C1	1.434 (2)	C10—C11	1.425 (3)
C1—C6	1.379 (3)	C10—H10A	0.9300
C1—C2	1.393 (2)	C11—C12	1.421 (3)
C2—C3	1.405 (2)	C12—C13	1.343 (2)
C2—C7	1.437 (3)	C12—H12A	0.9300
C3—C4	1.375 (3)	C13—H13A	0.9300
C3—C8	1.442 (3)	O1W—H1WA	0.98 (3)
C4—C5	1.377 (3)	O1W—H1WB	0.87 (3)
C4—H4A	0.9300

C9—N3—C13	118.73 (16)	C1—C6—H6A	119.9
C9—N3—C1	120.28 (15)	N1—C7—C2	178.2 (2)
C13—N3—C1	120.98 (15)	N2—C8—C3	179.4 (2)
C6—C1—C2	120.27 (17)	C10—C9—N3	122.07 (18)
C6—C1—N3	119.57 (16)	C10—C9—H9A	119.0
C2—C1—N3	120.14 (16)	N3—C9—H9A	119.0
C1—C2—C3	118.35 (16)	C9—C10—C11	121.43 (18)
C1—C2—C7	121.80 (16)	C9—C10—H10A	119.3
C3—C2—C7	119.73 (16)	C11—C10—H10A	119.3
C4—C3—C2	121.03 (17)	O1—C11—C12	122.52 (18)
C4—C3—C8	119.71 (17)	O1—C11—C10	123.01 (18)
C2—C3—C8	119.26 (17)	C12—C11—C10	114.47 (18)
C3—C4—C5	119.31 (18)	C13—C12—C11	122.10 (18)
C3—C4—H4A	120.3	C13—C12—H12A	119.0
C5—C4—H4A	120.3	C11—C12—H12A	119.0
C6—C5—C4	120.84 (19)	C12—C13—N3	121.17 (17)
C6—C5—H5A	119.6	C12—C13—H13A	119.4
C4—C5—H5A	119.6	N3—C13—H13A	119.4
C5—C6—C1	120.18 (18)	H1WA—O1W—H1WB	104 (3)
C5—C6—H6A	119.9

C9—N3—C1—C6	50.0 (3)	C2—C1—C6—C5	−0.7 (3)
C13—N3—C1—C6	−128.6 (2)	N3—C1—C6—C5	−178.7 (2)
C9—N3—C1—C2	−128.0 (2)	C1—C2—C7—N1	140 (7)
C13—N3—C1—C2	53.4 (3)	C3—C2—C7—N1	−36 (7)
C6—C1—C2—C3	1.7 (3)	C4—C3—C8—N2	−9 (28)
N3—C1—C2—C3	179.77 (17)	C2—C3—C8—N2	171 (100)
C6—C1—C2—C7	−174.18 (19)	C13—N3—C9—C10	−1.3 (3)
N3—C1—C2—C7	3.9 (3)	C1—N3—C9—C10	−179.9 (2)
C1—C2—C3—C4	−1.4 (3)	N3—C9—C10—C11	−0.2 (3)
C7—C2—C3—C4	174.61 (19)	C9—C10—C11—O1	−178.9 (2)
C1—C2—C3—C8	178.93 (18)	C9—C10—C11—C12	1.4 (3)
C7—C2—C3—C8	−5.1 (3)	O1—C11—C12—C13	179.2 (2)
C2—C3—C4—C5	0.0 (3)	C10—C11—C12—C13	−1.1 (3)
C8—C3—C4—C5	179.7 (2)	C11—C12—C13—N3	−0.4 (3)
C3—C4—C5—C6	1.1 (3)	C9—N3—C13—C12	1.6 (3)
C4—C5—C6—C1	−0.8 (3)	C1—N3—C13—C12	−179.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1	0.98 (3)	1.79 (3)	2.763 (2)	170 (3)
O1W—H1WB···O1ⁱ	0.87 (3)	1.88 (3)	2.721 (2)	162 (3)
C6—H6A···O1Wⁱⁱ	0.93	2.37	3.302 (3)	177
C13—H13A···O1Wⁱⁱⁱ	0.93	2.38	3.311 (3)	175
C9—H9A···N1^iv	0.93	2.55	3.440 (2)	160

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

Experimental details

Crystal data
Chemical formula	C₁₃H₇N₃O·H₂O
M_r	239.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.977 (2), 7.2497 (12), 13.850 (2)
β (°)	94.244 (3)
V (Å³)	1199.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.989, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	5795, 2112, 1349
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.124, 1.03
No. of reflections	2112
No. of parameters	172
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.14

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), 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
O1W—H1WA···O1	0.98 (3)	1.79 (3)	2.763 (2)	170 (3)
O1W—H1WB···O1ⁱ	0.87 (3)	1.88 (3)	2.721 (2)	162 (3)
C6—H6A···O1Wⁱⁱ	0.93	2.37	3.302 (3)	176.7
C13—H13A···O1Wⁱⁱⁱ	0.93	2.38	3.311 (3)	175.3
C9—H9A···N1^iv	0.93	2.55	3.440 (2)	160

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

References

Archibald, S. J., Blake, A. J., Schroder, M. & Winpenny, R. E. P. (1994). Chem. Commun. pp. 1669—1670. Google Scholar
Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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