Dioxo(pyridine-2-carboxyl­ato)(pyridinium-2-carboxyl­ato)vanadium(V) monohydrate

In the title compound, [VO₂(C₆H₄NO₂)(C₆H₅NO₂)]·H₂O, one of the two pyridine-2-carboxyl­ate ligands chelates to the V atom in a bidentate manner, via the carboxyl­ate O atom and the N atom of the pyridine ring. The second pyridine-2-carboxyl­ate ligand coordinates to the V atom only via the carboxyl­ate O atom, while the N atom of the pyridine ring is protonated. The coordination geometry of the V atom is distorted trigonal–bipyramidal. The crystal packing is stabilized by inter­molecular N—H...O, C—H...O and O—H...O hydrogen bonds involving the solvent water mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.092
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Dioxo(pyridine-2-carboxylato)(pyridinium-2-carboxylato)vanadium(V) monohydrate

Crystal data

[V(C6H4NO2)(C6H5NO2)O2]·H2O	Z = 2
Mr = 346.17	F(000) = 352
Triclinic, P1	Dx = 1.684 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3392 (15) Å	Cell parameters from 2766 reflections
b = 7.4413 (16) Å	θ = 1.4–25.5°
c = 14.592 (3) Å	µ = 0.77 mm^−1
α = 97.745 (3)°	T = 298 K
β = 94.787 (3)°	Slab, yellow
γ = 118.655 (3)°	0.48 × 0.14 × 0.09 mm
V = 682.8 (2) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2517 independent reflections
Radiation source: fine-focus sealed tube	2173 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 83.66 pixels mm^-1	θmax = 25.5°, θmin = 1.4°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −9→9
Tmin = 0.710, Tmax = 0.934	l = −17→17
6777 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.1867P] where P = (Fo^2 + 2Fc^2)/3
2517 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.33 e Å^−3
2 restraints	Δρmin = −0.22 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
V1	1.04796 (6)	0.27970 (6)	0.27528 (2)	0.03878 (15)
O1	1.1335 (3)	0.2726 (3)	0.05654 (11)	0.0536 (4)
O2	0.9156 (2)	0.2851 (3)	0.15288 (10)	0.0466 (4)
O3	0.5435 (3)	0.1644 (3)	0.40312 (13)	0.0628 (5)
O4	0.7719 (2)	0.2424 (3)	0.30430 (11)	0.0445 (4)
O5	1.2725 (3)	0.4898 (3)	0.29096 (13)	0.0656 (5)
O6	1.0791 (4)	0.0817 (3)	0.24722 (12)	0.0691 (6)
O1W	0.5718 (3)	0.3843 (4)	0.18236 (14)	0.0623 (5)
C5	0.8118 (3)	0.2435 (3)	−0.00689 (15)	0.0366 (5)
N2	1.0644 (3)	0.2714 (3)	0.42062 (12)	0.0361 (4)
C4	0.8218 (4)	0.1897 (4)	−0.09964 (16)	0.0446 (5)
H4A	0.9318	0.1698	−0.1156	0.054*
C3	0.6669 (4)	0.1656 (4)	−0.16872 (17)	0.0518 (6)
H3A	0.6707	0.1264	−0.2315	0.062*
C2	0.5071 (4)	0.1995 (4)	−0.14474 (17)	0.0505 (6)
H2A	0.4044	0.1872	−0.1910	0.061*
C1	0.5015 (4)	0.2516 (4)	−0.05182 (17)	0.0461 (6)
H1A	0.3936	0.2737	−0.0345	0.055*
N1	0.6507 (3)	0.2706 (3)	0.01390 (13)	0.0387 (4)
H1B	0.6435	0.3015	0.0719	0.046*
C6	0.9726 (3)	0.2693 (3)	0.07291 (15)	0.0384 (5)
C12	0.7158 (3)	0.2102 (3)	0.38559 (16)	0.0415 (5)
C11	0.8906 (3)	0.2353 (3)	0.45656 (15)	0.0368 (5)
C10	0.8750 (4)	0.2231 (4)	0.54900 (16)	0.0470 (6)
H10A	0.7514	0.1963	0.5715	0.056*
C9	1.0494 (4)	0.2520 (4)	0.60743 (17)	0.0520 (6)
H9A	1.0454	0.2463	0.6705	0.062*
C8	1.2288 (4)	0.2894 (4)	0.57124 (17)	0.0528 (6)
H8A	1.3473	0.3096	0.6098	0.063*
C7	1.2317 (4)	0.2968 (4)	0.47699 (17)	0.0460 (5)
H7A	1.3523	0.3198	0.4525	0.055*
H1WA	0.607 (6)	0.323 (5)	0.218 (2)	0.104 (14)*
H1WB	0.452 (3)	0.362 (6)	0.192 (3)	0.117 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
V1	0.0353 (2)	0.0530 (3)	0.0359 (2)	0.02716 (19)	0.01194 (16)	0.00913 (17)
O1	0.0441 (10)	0.0799 (12)	0.0474 (10)	0.0379 (9)	0.0151 (8)	0.0123 (9)
O2	0.0438 (9)	0.0699 (11)	0.0367 (8)	0.0358 (8)	0.0109 (7)	0.0112 (7)
O3	0.0420 (10)	0.0917 (14)	0.0673 (12)	0.0378 (10)	0.0254 (9)	0.0266 (10)
O4	0.0370 (8)	0.0641 (10)	0.0385 (8)	0.0289 (8)	0.0119 (7)	0.0108 (7)
O5	0.0397 (10)	0.0877 (14)	0.0543 (11)	0.0164 (10)	0.0094 (8)	0.0279 (10)
O6	0.1106 (17)	0.0968 (15)	0.0427 (10)	0.0842 (14)	0.0206 (10)	0.0121 (9)
O1W	0.0611 (12)	0.0932 (15)	0.0594 (12)	0.0553 (12)	0.0249 (10)	0.0214 (11)
C5	0.0362 (11)	0.0343 (11)	0.0379 (11)	0.0160 (9)	0.0100 (9)	0.0067 (9)
N2	0.0353 (10)	0.0375 (10)	0.0369 (9)	0.0194 (8)	0.0089 (8)	0.0048 (7)
C4	0.0468 (13)	0.0485 (13)	0.0407 (12)	0.0256 (11)	0.0118 (10)	0.0055 (10)
C3	0.0582 (16)	0.0528 (14)	0.0371 (13)	0.0238 (13)	0.0031 (11)	0.0042 (11)
C2	0.0469 (14)	0.0488 (14)	0.0488 (14)	0.0211 (12)	−0.0050 (11)	0.0071 (11)
C1	0.0380 (12)	0.0469 (13)	0.0558 (14)	0.0227 (11)	0.0077 (10)	0.0110 (11)
N1	0.0379 (10)	0.0409 (10)	0.0380 (10)	0.0198 (8)	0.0097 (8)	0.0073 (8)
C6	0.0373 (12)	0.0401 (12)	0.0391 (12)	0.0197 (10)	0.0097 (9)	0.0078 (9)
C12	0.0371 (12)	0.0449 (13)	0.0466 (13)	0.0219 (10)	0.0150 (10)	0.0108 (10)
C11	0.0374 (11)	0.0322 (11)	0.0410 (12)	0.0169 (9)	0.0123 (9)	0.0066 (9)
C10	0.0506 (14)	0.0435 (13)	0.0459 (13)	0.0205 (11)	0.0193 (11)	0.0109 (10)
C9	0.0649 (17)	0.0499 (14)	0.0394 (13)	0.0258 (13)	0.0117 (12)	0.0123 (11)
C8	0.0560 (15)	0.0516 (14)	0.0460 (14)	0.0254 (13)	−0.0024 (11)	0.0068 (11)
C7	0.0409 (13)	0.0525 (14)	0.0478 (13)	0.0262 (11)	0.0084 (10)	0.0078 (11)

Geometric parameters (Å, º)

V1—O6	1.6024 (18)	C4—H4A	0.9300
V1—O5	1.6066 (18)	C3—C2	1.375 (4)
V1—O2	1.9755 (16)	C3—H3A	0.9300
V1—O4	1.9990 (16)	C2—C1	1.369 (3)
V1—N2	2.1252 (18)	C2—H2A	0.9300
O1—C6	1.214 (3)	C1—N1	1.334 (3)
O2—C6	1.281 (3)	C1—H1A	0.9300
O3—C12	1.202 (3)	N1—H1B	0.8600
O4—C12	1.303 (3)	C12—C11	1.500 (3)
O1W—H1WA	0.84 (4)	C11—C10	1.375 (3)
O1W—H1WB	0.84 (3)	C10—C9	1.384 (4)
C5—N1	1.342 (3)	C10—H10A	0.9300
C5—C4	1.377 (3)	C9—C8	1.376 (4)
C5—C6	1.509 (3)	C9—H9A	0.9300
N2—C7	1.337 (3)	C8—C7	1.385 (3)
N2—C11	1.340 (3)	C8—H8A	0.9300
C4—C3	1.380 (3)	C7—H7A	0.9300
O6—V1—O5	109.13 (12)	N1—C1—C2	120.0 (2)
O6—V1—O2	100.79 (8)	N1—C1—H1A	120.0
O5—V1—O2	101.11 (8)	C2—C1—H1A	120.0
O6—V1—O4	120.74 (10)	C1—N1—C5	122.6 (2)
O5—V1—O4	129.38 (10)	C1—N1—H1B	118.7
O2—V1—O4	78.70 (6)	C5—N1—H1B	118.7
O6—V1—N2	94.65 (8)	O1—C6—O2	127.9 (2)
O5—V1—N2	93.24 (8)	O1—C6—C5	119.73 (19)
O2—V1—N2	154.05 (7)	O2—C6—C5	112.41 (18)
O4—V1—N2	75.49 (6)	O3—C12—O4	124.6 (2)
C6—O2—V1	127.94 (14)	O3—C12—C11	122.7 (2)
C12—O4—V1	122.22 (14)	O4—C12—C11	112.63 (18)
H1WA—O1W—H1WB	106 (4)	N2—C11—C10	123.3 (2)
N1—C5—C4	118.9 (2)	N2—C11—C12	113.01 (18)
N1—C5—C6	118.36 (18)	C10—C11—C12	123.7 (2)
C4—C5—C6	122.7 (2)	C11—C10—C9	117.8 (2)
C7—N2—C11	118.75 (19)	C11—C10—H10A	121.1
C7—N2—V1	125.10 (15)	C9—C10—H10A	121.1
C11—N2—V1	116.15 (14)	C8—C9—C10	119.4 (2)
C5—C4—C3	119.4 (2)	C8—C9—H9A	120.3
C5—C4—H4A	120.3	C10—C9—H9A	120.3
C3—C4—H4A	120.3	C9—C8—C7	119.5 (2)
C2—C3—C4	120.0 (2)	C9—C8—H8A	120.2
C2—C3—H3A	120.0	C7—C8—H8A	120.2
C4—C3—H3A	120.0	N2—C7—C8	121.3 (2)
C1—C2—C3	119.0 (2)	N2—C7—H7A	119.4
C1—C2—H2A	120.5	C8—C7—H7A	119.4
C3—C2—H2A	120.5
O6—V1—O2—C6	−46.8 (2)	V1—O2—C6—O1	−9.6 (3)
O5—V1—O2—C6	65.4 (2)	V1—O2—C6—C5	170.25 (13)
O4—V1—O2—C6	−166.30 (19)	N1—C5—C6—O1	−170.5 (2)
N2—V1—O2—C6	−172.27 (17)	C4—C5—C6—O1	10.7 (3)
O6—V1—O4—C12	80.03 (19)	N1—C5—C6—O2	9.7 (3)
O5—V1—O4—C12	−88.87 (19)	C4—C5—C6—O2	−169.1 (2)
O2—V1—O4—C12	175.95 (18)	V1—O4—C12—O3	−171.5 (2)
N2—V1—O4—C12	−6.74 (17)	V1—O4—C12—C11	8.2 (3)
O6—V1—N2—C7	62.28 (19)	C7—N2—C11—C10	0.1 (3)
O5—V1—N2—C7	−47.22 (19)	V1—N2—C11—C10	179.34 (17)
O2—V1—N2—C7	−171.10 (17)	C7—N2—C11—C12	179.93 (18)
O4—V1—N2—C7	−177.14 (19)	V1—N2—C11—C12	−0.8 (2)
O6—V1—N2—C11	−116.94 (17)	O3—C12—C11—N2	175.3 (2)
O5—V1—N2—C11	133.56 (16)	O4—C12—C11—N2	−4.3 (3)
O2—V1—N2—C11	9.7 (3)	O3—C12—C11—C10	−4.8 (4)
O4—V1—N2—C11	3.64 (14)	O4—C12—C11—C10	175.5 (2)
N1—C5—C4—C3	0.2 (3)	N2—C11—C10—C9	0.7 (3)
C6—C5—C4—C3	178.9 (2)	C12—C11—C10—C9	−179.1 (2)
C5—C4—C3—C2	1.4 (4)	C11—C10—C9—C8	−0.6 (3)
C4—C3—C2—C1	−1.7 (4)	C10—C9—C8—C7	−0.2 (4)
C3—C2—C1—N1	0.6 (4)	C11—N2—C7—C8	−1.0 (3)
C2—C1—N1—C5	1.0 (3)	V1—N2—C7—C8	179.85 (17)
C4—C5—N1—C1	−1.4 (3)	C9—C8—C7—N2	1.0 (4)
C6—C5—N1—C1	179.83 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2	0.86	2.30	2.643 (3)	104
O1W—H1WA···O4	0.84 (4)	2.01 (4)	2.828 (3)	164 (4)
N1—H1B···O1W	0.86	1.85	2.691 (3)	164
O1W—H1WB···O5^i	0.84 (3)	2.42 (4)	3.139 (3)	143 (4)
C1—H1A···O1^i	0.93	2.41	3.297 (4)	159
C4—H4A···O6^ii	0.93	2.46	3.121 (4)	128
C7—H7A···O3^iii	0.93	2.31	3.108 (4)	144

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