Pyridinium cis-diaqua-bis-(oxalato-κ(2)O,O')chromate(III).

The title compound, (C(5)H(6)N)[Cr(C(2)O(4))(2)(H(2)O)(2)], contains one protonated pyridine mol-ecule and one [Cr(C(2)O(4))(2)(H(2)O)(2)](-) complex anion in the asymmetric unit. The Cr(III) in the complex anion is coordinated in a distorted octa-hedral environment by two O atoms from two cis water mol-ecules and four O atoms from two chelating oxalate dianions. The crystal packing is stabilized by inter-molecular N-H⋯O(oxalate) and O-H⋯O(oxalate) hydrogen bonds and by π-π stacking inter-actions (centroid-centroid distance = 3.602 Å) between pyridine rings, thereby building up a three-dimensional network.

Related literature

For the structural characterization of organic–inorganic salts containing the [Cr(C2O4)2(H2O)2]− anion, see: Bélombé et al. (2009 ▶); Nenwa et al. (2010 ▶, 2012 ▶); Chérif et al. (2011 ▶); Chérif, Abdelhak et al. (2012 ▶); Chérif, Zid et al. (2012 ▶).

Experimental

Crystal data

(C5H6N)[Cr(C2O4)2(H2O)2]

M = 344.18

Monoclinic,

a = 7.479 (2) Å

b = 24.700 (8) Å

c = 7.056 (2) Å

β = 107.744 (6)°

V = 1241.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.98 mm−1

T = 100 K

0.15 × 0.04 × 0.04 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.862, T max = 0.961

18649 measured reflections

3703 independent reflections

2580 reflections with I > 2σ(I)

R int = 0.106

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.160

S = 1.13

3703 reflections

206 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.69 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044303/lr2086sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044303/lr2086Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C5H6N)[Cr(C2O4)2(H2O)2]	F(000) = 700
Mr = 344.18	Dx = 1.842 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P_2ybc	Cell parameters from 3703 reflections
a = 7.479 (2) Å	θ = 1.7–30.9°
b = 24.700 (8) Å	µ = 0.98 mm−1
c = 7.056 (2) Å	T = 100 K
β = 107.744 (6)°	Needle, violet
V = 1241.4 (6) Å3	0.15 × 0.04 × 0.04 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3703 independent reflections
Radiation source: fine-focus sealed tube	2580 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.106
φ and ω scans	θmax = 30.9°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
Tmin = 0.862, Tmax = 0.961	k = −34→33
18649 measured reflections	l = −9→10

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0636P)2] where P = (Fo2 + 2Fc2)/3
3703 reflections	(Δ/σ)max = 0.001
206 parameters	Δρmax = 0.59 e Å−3
5 restraints	Δρmin = −0.69 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
Cr1	0.00150 (8)	0.67285 (2)	0.06297 (8)	0.00840 (15)
C11	−0.3839 (5)	0.67581 (15)	−0.0409 (5)	0.0119 (7)
C12	−0.3217 (5)	0.73552 (14)	−0.0479 (5)	0.0099 (7)
C21	0.0773 (5)	0.61425 (14)	−0.2335 (5)	0.0110 (7)
C22	0.1456 (5)	0.57906 (15)	−0.0428 (5)	0.0120 (7)
O11	−0.2502 (3)	0.64143 (10)	0.0020 (4)	0.0113 (5)
O12	−0.1425 (3)	0.74032 (10)	−0.0051 (4)	0.0105 (5)
O13	−0.4367 (4)	0.77229 (11)	−0.0905 (4)	0.0177 (6)
O14	−0.5518 (4)	0.66425 (11)	−0.0766 (4)	0.0170 (6)
O21	0.0065 (3)	0.65975 (10)	−0.2098 (4)	0.0113 (5)
O22	0.1238 (4)	0.60185 (10)	0.1125 (4)	0.0118 (5)
O23	0.0948 (4)	0.59673 (10)	−0.3912 (4)	0.0137 (5)
O24	0.2113 (4)	0.53428 (11)	−0.0504 (4)	0.0186 (6)
OW1	0.0262 (4)	0.67909 (11)	0.3493 (4)	0.0139 (5)
OW2	0.2371 (4)	0.71532 (11)	0.1053 (4)	0.0139 (5)
N1	0.2547 (4)	0.48994 (13)	−0.3963 (5)	0.0148 (6)
H1	0.2081	0.5152	−0.3419	0.018*
C2	0.3312 (6)	0.44697 (16)	−0.2871 (6)	0.0177 (8)
H2	0.3320	0.4446	−0.1553	0.021*
C3	0.2476 (5)	0.49522 (15)	−0.5870 (6)	0.0147 (7)
H3	0.1927	0.5256	−0.6590	0.018*
C4	0.3220 (6)	0.45543 (16)	−0.6751 (6)	0.0172 (8)
H4	0.3164	0.4583	−0.8082	0.021*
C5	0.4083 (5)	0.40652 (15)	−0.3686 (6)	0.0180 (8)
H5	0.4618	0.3765	−0.2930	0.022*
C6	0.4059 (5)	0.41073 (16)	−0.5641 (6)	0.0161 (8)
H6	0.4599	0.3839	−0.6212	0.019*
H1B	−0.019 (6)	0.6988 (17)	0.415 (6)	0.032 (15)*
H2A	0.310 (5)	0.721 (2)	0.214 (4)	0.033 (15)*
H1A	0.051 (8)	0.6501 (17)	0.419 (9)	0.06 (2)*
H2B	0.296 (6)	0.700 (2)	0.040 (6)	0.06 (2)*

	U11	U22	U33	U12	U13	U23
Cr1	0.0108 (3)	0.0067 (3)	0.0083 (3)	0.0012 (2)	0.0037 (2)	0.0006 (2)
C11	0.0116 (16)	0.0135 (17)	0.0112 (17)	0.0003 (13)	0.0043 (13)	0.0004 (14)
C12	0.0122 (16)	0.0114 (16)	0.0052 (16)	0.0005 (13)	0.0015 (13)	0.0007 (12)
C21	0.0141 (17)	0.0108 (17)	0.0102 (17)	−0.0011 (13)	0.0065 (14)	−0.0005 (13)
C22	0.0157 (17)	0.0120 (17)	0.0095 (17)	0.0011 (13)	0.0056 (14)	0.0046 (14)
O11	0.0123 (12)	0.0093 (12)	0.0129 (13)	−0.0006 (9)	0.0048 (10)	−0.0011 (9)
O12	0.0116 (12)	0.0086 (12)	0.0110 (13)	0.0004 (9)	0.0031 (10)	0.0003 (9)
O13	0.0148 (13)	0.0116 (13)	0.0250 (16)	0.0046 (10)	0.0035 (11)	0.0026 (11)
O14	0.0128 (12)	0.0175 (14)	0.0222 (15)	−0.0043 (10)	0.0073 (11)	−0.0070 (11)
O21	0.0132 (12)	0.0094 (12)	0.0123 (13)	0.0012 (9)	0.0053 (10)	−0.0014 (9)
O22	0.0187 (13)	0.0109 (13)	0.0074 (12)	0.0035 (10)	0.0061 (10)	0.0021 (10)
O23	0.0205 (13)	0.0112 (13)	0.0109 (13)	0.0017 (10)	0.0069 (10)	0.0004 (10)
O24	0.0351 (16)	0.0092 (13)	0.0144 (14)	0.0103 (11)	0.0119 (12)	0.0024 (10)
OW1	0.0217 (14)	0.0106 (13)	0.0106 (13)	0.0050 (11)	0.0069 (11)	−0.0003 (10)
OW2	0.0108 (12)	0.0163 (14)	0.0150 (14)	−0.0020 (10)	0.0044 (11)	−0.0048 (11)
N1	0.0198 (16)	0.0104 (15)	0.0167 (16)	−0.0004 (12)	0.0090 (13)	−0.0021 (12)
C2	0.028 (2)	0.0151 (19)	0.0117 (18)	−0.0035 (16)	0.0091 (16)	−0.0003 (14)
C3	0.0166 (18)	0.0114 (17)	0.0139 (18)	−0.0028 (13)	0.0013 (14)	0.0026 (14)
C4	0.024 (2)	0.0173 (19)	0.0100 (18)	−0.0015 (15)	0.0040 (15)	−0.0013 (14)
C5	0.024 (2)	0.0083 (17)	0.019 (2)	0.0024 (14)	0.0037 (16)	0.0042 (14)
C6	0.0199 (19)	0.0129 (18)	0.017 (2)	0.0007 (14)	0.0068 (15)	−0.0062 (14)

Cr1—O11	1.959 (3)	OW1—H1B	0.814 (19)
Cr1—O22	1.960 (3)	OW1—H1A	0.86 (5)
Cr1—O12	1.963 (3)	OW2—H2A	0.806 (19)
Cr1—O21	1.963 (3)	OW2—H2B	0.818 (19)
Cr1—OW1	1.978 (3)	N1—C2	1.334 (5)
Cr1—OW2	1.993 (3)	N1—C3	1.337 (5)
C11—O14	1.237 (4)	N1—H1	0.8600
C11—O11	1.276 (4)	C2—C5	1.365 (5)
C11—C12	1.552 (5)	C2—H2	0.9300
C12—O13	1.224 (4)	C3—C4	1.369 (5)
C12—O12	1.286 (4)	C3—H3	0.9300
C21—O23	1.238 (4)	C4—C6	1.388 (5)
C21—O21	1.275 (4)	C4—H4	0.9300
C21—C22	1.552 (5)	C5—C6	1.378 (6)
C22—O24	1.218 (4)	C5—H5	0.9300
C22—O22	1.285 (4)	C6—H6	0.9300
O11—Cr1—O22	92.85 (11)	C12—O12—Cr1	115.7 (2)
O11—Cr1—O12	82.18 (10)	C21—O21—Cr1	114.0 (2)
O22—Cr1—O12	174.30 (11)	C22—O22—Cr1	114.4 (2)
O11—Cr1—O21	91.36 (11)	Cr1—OW1—H1B	135 (3)
O22—Cr1—O21	83.09 (11)	Cr1—OW1—H1A	117 (4)
O12—Cr1—O21	94.19 (11)	H1B—OW1—H1A	103 (4)
O11—Cr1—OW1	92.26 (11)	Cr1—OW2—H2A	123 (4)
O22—Cr1—OW1	89.69 (11)	Cr1—OW2—H2B	106 (4)
O12—Cr1—OW1	93.28 (11)	H2A—OW2—H2B	107 (3)
O21—Cr1—OW1	172.08 (11)	C2—N1—C3	122.5 (3)
O11—Cr1—OW2	171.04 (11)	C2—N1—H1	118.8
O22—Cr1—OW2	95.79 (11)	C3—N1—H1	118.8
O12—Cr1—OW2	89.07 (11)	N1—C2—C5	120.1 (4)
O21—Cr1—OW2	87.33 (11)	N1—C2—H2	120.0
OW1—Cr1—OW2	90.17 (12)	C5—C2—H2	120.0
O14—C11—O11	124.7 (3)	N1—C3—C4	119.4 (3)
O14—C11—C12	120.6 (3)	N1—C3—H3	120.3
O11—C11—C12	114.8 (3)	C4—C3—H3	120.3
O13—C12—O12	126.4 (3)	C3—C4—C6	119.4 (4)
O13—C12—C11	121.2 (3)	C3—C4—H4	120.3
O12—C12—C11	112.4 (3)	C6—C4—H4	120.3
O23—C21—O21	126.0 (3)	C2—C5—C6	119.2 (4)
O23—C21—C22	119.1 (3)	C2—C5—H5	120.4
O21—C21—C22	114.9 (3)	C6—C5—H5	120.4
O24—C22—O22	126.3 (3)	C5—C6—C4	119.4 (4)
O24—C22—C21	120.1 (3)	C5—C6—H6	120.3
O22—C22—C21	113.6 (3)	C4—C6—H6	120.3
C11—O11—Cr1	114.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O24	0.86	2.10	2.783 (4)	136
N1—H1···O23	0.86	2.17	2.901 (4)	143
OW1—H1B···O12i	0.81 (2)	1.94 (2)	2.720 (4)	162 (5)
OW1—H1A···O23ii	0.86 (5)	1.84 (5)	2.680 (4)	168 (5)
OW2—H2A···O13iii	0.81 (2)	1.98 (3)	2.732 (4)	154 (4)
OW2—H2B···O14iv	0.82 (2)	1.83 (2)	2.639 (4)	173 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O24	0.86	2.10	2.783 (4)	136
N1—H1⋯O23	0.86	2.17	2.901 (4)	143
OW1—H1B⋯O12i	0.81 (2)	1.94 (2)	2.720 (4)	162 (5)
OW1—H1A⋯O23ii	0.86 (5)	1.84 (5)	2.680 (4)	168 (5)
OW2—H2A⋯O13iii	0.81 (2)	1.98 (3)	2.732 (4)	154 (4)
OW2—H2B⋯O14iv	0.82 (2)	1.83 (2)	2.639 (4)	173 (5)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .