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

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.124
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     --  C7      ..        6.2 su
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.718
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          8
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C2     -   C7     ...       1.44 Ang.
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C3     -   C8     ...       1.44 Ang.
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            C1  -C2  -C7  -N1    140.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         20
            C3  -C2  -C7  -N1    -36.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         21
            C4  -C3  -C8  -N2     -9.00 28.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         22
            C2  -C3  -C8  -N2     17.00  0.00   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

S1. Comment

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

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

S2. Experimental

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

S3. Refinement

All hydrogen atoms bound to carbon were refined using a riding model with distance C—H = 0.93 Å, U_iso = 1.2U_eq (C) for aromatic atoms. The H atoms of the water molecule were located from difference density maps and were refined isotrpically.

Computing details

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

	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

Crystal data

C13H7N3O·H2O	F(000) = 496
Mr = 239.23	Dx = 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) Å^3	0.12 × 0.10 × 0.08 mm
Z = 4

Data collection

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

Refinement

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

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	0.87 (3)	1.88 (3)	2.721 (2)	162 (3)
C6—H6A···O1W^ii	0.93	2.37	3.302 (3)	177
C13—H13A···O1W^iii	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.