2-Amino-6-methyl-pyridinium trans-di-aqua-dioxalatochromate(III) monohydrate.

In the title compound, (C6H9N2)[Cr(C2O4)2(H2O)2]·H2O, the Cr(III) atom adopts a slightly distorted octa-hedral coordination environment defined by two chelating oxalate ligands in the equatorial plane and two water mol-ecules in axial positions. A three-dimensional network is generated by inter-molecular N-H⋯O and O-H⋯O hydrogen-bonding interactions involving the cation, the complex anion and the lattice water molecule.

Related literature

For general background to the coordination chemistry of oxalates, see: Martin et al. (2007 ▶). 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 ▶); Chérif et al. (2011 ▶); Chérif, Abdelhak et al. (2012 ▶); Chérif, Zid et al. (2012 ▶). For C—O bond lengths in oxalate anions, see: Marinescu et al. (2000 ▶). For geometric parameters of the 2-amino-6-methyl­pyridinium cation, see: Fun et al. (2008 ▶, 2009 ▶, 2010 ▶); Jebas et al. (2009 ▶); Quah et al. (2008 ▶); Ramesh et al. (2010 ▶); Rotondo et al. (2009 ▶); Pan et al. (2008 ▶). For discussion of hydrogen bonding, see: Blessing (1986 ▶); Brown (1976 ▶).

Experimental

Crystal data

(C6H9N2)[Cr(C2O4)2(H2O)2]·H2O

M = 391.24

Monoclinic,

a = 18.572 (3) Å

b = 11.025 (2) Å

c = 14.975 (3) Å

β = 96.28 (2)°

V = 3047.8 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.81 mm−1

T = 298 K

0.56 × 0.42 × 0.33 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.679, T max = 0.764

4604 measured reflections

3312 independent reflections

2896 reflections with I > 2σ(I)

R int = 0.037

2 standard reflections every 120 min intensity decay: 3.2%

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.112

S = 1.07

3312 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CAD-4 EXPRESS (Duisenberg, 1992 ▶; Macíček & Yordanov, 1992 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813022058/mw2113sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022058/mw2113Isup2.hkl

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

(C6H9N2)[Cr(C2O4)2(H2O)2]·H2O	F(000) = 1608
Mr = 391.24	Dx = 1.705 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 18.572 (3) Å	θ = 10–15°
b = 11.025 (2) Å	µ = 0.81 mm−1
c = 14.975 (3) Å	T = 298 K
β = 96.28 (2)°	Prism, pink
V = 3047.8 (10) Å3	0.56 × 0.42 × 0.33 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	2896 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 27.0°, θmin = 2.2°
non–profiled ω/2θ scans	h = −23→23
Absorption correction: ψ scan (North et al., 1968)	k = −1→14
Tmin = 0.679, Tmax = 0.764	l = −19→3
4604 measured reflections	2 standard reflections every 120 min
3312 independent reflections	intensity decay: 3.2%

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)] = 0.040	Hydrogen site location: mixed
wR(F2) = 0.112	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0677P)2 + 2.2239P] where P = (Fo2 + 2Fc2)/3
3312 reflections	(Δ/σ)max = 0.001
218 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

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 > 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.

	x	y	z	Uiso*/Ueq
Cr1	0.32255 (2)	0.27746 (3)	0.19839 (2)	0.02219 (13)
O1	0.38682 (8)	0.29143 (13)	0.09943 (9)	0.0291 (3)
H3	0.3720	0.2466	0.0568	0.044*
H4	0.4279	0.2639	0.1150	0.044*
O2	0.25655 (9)	0.26707 (13)	0.29364 (10)	0.0325 (3)
H2	0.2587	0.3260	0.3284	0.049*
H10	0.2578	0.2050	0.3251	0.049*
O3	0.24053 (8)	0.26015 (12)	0.10486 (9)	0.0259 (3)
O4	0.40928 (8)	0.28451 (13)	0.28656 (10)	0.0315 (3)
O5	0.29813 (8)	0.45160 (12)	0.18501 (10)	0.0290 (3)
O6	0.33921 (8)	0.10332 (13)	0.20991 (9)	0.0284 (3)
O7	0.15703 (8)	0.37130 (15)	0.02425 (10)	0.0379 (4)
O8	0.22682 (10)	0.57497 (14)	0.09691 (10)	0.0374 (4)
O9	0.40914 (10)	−0.03256 (15)	0.28778 (13)	0.0468 (4)
O10	0.49100 (8)	0.16363 (17)	0.36144 (11)	0.0389 (4)
O11	0.24742 (10)	−0.05094 (17)	0.09548 (11)	0.0480 (5)
H1	0.2610	−0.0620	0.0451	0.072*
H11	0.2725	0.0015	0.1239	0.072*
N1	0.49218 (10)	0.78135 (16)	0.37925 (13)	0.0325 (4)
H7	0.4632	0.8434	0.3532	0.039*
N2	0.56211 (12)	0.93977 (19)	0.43928 (15)	0.0455 (5)
H5	0.6002	0.9646	0.4807	0.055*
H13	0.5320	0.9978	0.4096	0.055*
C1	0.21055 (11)	0.35961 (17)	0.07919 (12)	0.0246 (4)
C2	0.43552 (11)	0.1812 (2)	0.31024 (13)	0.0281 (4)
C3	0.24748 (11)	0.47407 (17)	0.12350 (13)	0.0254 (4)
C4	0.39248 (11)	0.07128 (19)	0.26753 (14)	0.0288 (4)
C5	0.52196 (14)	0.5768 (2)	0.4038 (2)	0.0480 (6)
H12	0.5124	0.4947	0.3949	0.058*
C6	0.58452 (15)	0.6150 (3)	0.4566 (2)	0.0518 (7)
H9	0.6165	0.5570	0.4830	0.062*
C7	0.59978 (14)	0.7335 (3)	0.47029 (18)	0.0449 (6)
H6	0.6416	0.7570	0.5061	0.054*
C8	0.47476 (13)	0.6629 (2)	0.36524 (17)	0.0397 (5)
C9	0.40503 (15)	0.6364 (3)	0.3091 (2)	0.0587 (8)
H8	0.3659	0.6395	0.3460	0.088*
H14	0.4072	0.5570	0.2832	0.088*
H15	0.3971	0.6956	0.2621	0.088*
C10	0.55186 (12)	0.8210 (2)	0.42989 (15)	0.0337 (5)

	U11	U22	U33	U12	U13	U23
Cr1	0.02305 (19)	0.01884 (19)	0.02292 (19)	0.00059 (11)	−0.00543 (12)	0.00012 (10)
O1	0.0281 (7)	0.0301 (7)	0.0279 (7)	−0.0021 (6)	−0.0021 (6)	−0.0019 (6)
O2	0.0400 (8)	0.0271 (8)	0.0304 (8)	0.0037 (6)	0.0047 (6)	0.0027 (6)
O3	0.0260 (7)	0.0220 (7)	0.0278 (7)	−0.0003 (5)	−0.0059 (5)	−0.0012 (5)
O4	0.0305 (8)	0.0311 (8)	0.0302 (8)	−0.0023 (6)	−0.0088 (6)	−0.0015 (6)
O5	0.0329 (7)	0.0200 (6)	0.0317 (7)	0.0001 (6)	−0.0071 (6)	−0.0014 (5)
O6	0.0272 (7)	0.0228 (7)	0.0330 (7)	0.0015 (6)	−0.0062 (6)	0.0006 (6)
O7	0.0356 (8)	0.0361 (8)	0.0377 (8)	0.0107 (7)	−0.0152 (7)	−0.0085 (7)
O8	0.0545 (10)	0.0220 (7)	0.0333 (8)	0.0083 (7)	−0.0054 (7)	0.0007 (6)
O9	0.0468 (10)	0.0309 (9)	0.0602 (11)	0.0099 (7)	−0.0058 (8)	0.0134 (8)
O10	0.0261 (7)	0.0521 (10)	0.0359 (8)	0.0011 (7)	−0.0087 (6)	0.0098 (7)
O11	0.0649 (12)	0.0413 (10)	0.0375 (9)	−0.0201 (9)	0.0042 (8)	0.0002 (7)
N1	0.0279 (9)	0.0289 (9)	0.0396 (10)	0.0063 (7)	−0.0012 (7)	0.0018 (7)
N2	0.0462 (12)	0.0356 (10)	0.0534 (12)	−0.0063 (9)	−0.0005 (9)	−0.0046 (9)
C1	0.0270 (9)	0.0249 (10)	0.0214 (9)	0.0032 (7)	−0.0002 (7)	−0.0016 (7)
C2	0.0229 (9)	0.0371 (11)	0.0240 (9)	0.0005 (8)	0.0003 (7)	0.0042 (8)
C3	0.0316 (10)	0.0229 (9)	0.0215 (9)	0.0017 (7)	0.0015 (7)	−0.0015 (7)
C4	0.0264 (10)	0.0280 (10)	0.0312 (10)	0.0029 (8)	0.0005 (8)	0.0053 (8)
C5	0.0487 (15)	0.0287 (11)	0.0673 (17)	0.0031 (11)	0.0094 (13)	0.0012 (11)
C6	0.0435 (14)	0.0473 (14)	0.0639 (17)	0.0152 (12)	0.0029 (12)	0.0120 (13)
C7	0.0331 (12)	0.0506 (15)	0.0486 (14)	0.0068 (10)	−0.0061 (11)	0.0036 (11)
C8	0.0338 (11)	0.0353 (12)	0.0509 (14)	−0.0016 (9)	0.0087 (10)	−0.0066 (10)
C9	0.0378 (13)	0.0634 (19)	0.0733 (19)	−0.0083 (13)	−0.0011 (13)	−0.0253 (15)
C10	0.0295 (10)	0.0381 (12)	0.0334 (11)	0.0027 (9)	0.0028 (8)	0.0033 (9)

Cr1—O6	1.9493 (15)	N1—C10	1.346 (3)
Cr1—O3	1.9626 (14)	N1—C8	1.357 (3)
Cr1—O4	1.9695 (15)	N1—H7	0.9300
Cr1—O5	1.9778 (15)	N2—C10	1.328 (3)
Cr1—O2	1.9830 (15)	N2—H5	0.9300
Cr1—O1	2.0080 (15)	N2—H13	0.9300
O1—H3	0.8300	C1—C3	1.550 (3)
O1—H4	0.8300	C2—C4	1.551 (3)
O2—H2	0.8299	C5—C8	1.375 (4)
O2—H10	0.8300	C5—C6	1.397 (4)
O3—C1	1.270 (2)	C5—H12	0.9300
O4—C2	1.274 (3)	C6—C7	1.348 (4)
O5—C3	1.267 (2)	C6—H9	0.9300
O6—C4	1.289 (2)	C7—C10	1.404 (3)
O7—C1	1.226 (2)	C7—H6	0.9300
O8—C3	1.229 (2)	C8—C9	1.494 (4)
O9—C4	1.216 (3)	C9—H8	0.9600
O10—C2	1.231 (2)	C9—H14	0.9600
O11—H1	0.8299	C9—H15	0.9600
O11—H11	0.8301
O6—Cr1—O3	94.05 (6)	O7—C1—C3	119.34 (17)
O6—Cr1—O4	82.49 (6)	O3—C1—C3	114.48 (16)
O3—Cr1—O4	175.08 (6)	O10—C2—O4	125.7 (2)
O6—Cr1—O5	175.89 (6)	O10—C2—C4	119.50 (19)
O3—Cr1—O5	82.57 (6)	O4—C2—C4	114.82 (16)
O4—Cr1—O5	101.03 (6)	O8—C3—O5	126.40 (19)
O6—Cr1—O2	89.09 (6)	O8—C3—C1	119.36 (18)
O3—Cr1—O2	90.87 (7)	O5—C3—C1	114.24 (16)
O4—Cr1—O2	92.56 (7)	O9—C4—O6	125.5 (2)
O5—Cr1—O2	88.63 (6)	O9—C4—C2	121.83 (19)
O6—Cr1—O1	92.26 (6)	O6—C4—C2	112.65 (17)
O3—Cr1—O1	87.62 (6)	C8—C5—C6	118.9 (2)
O4—Cr1—O1	89.03 (6)	C8—C5—H12	120.6
O5—Cr1—O1	89.94 (6)	C6—C5—H12	120.6
O2—Cr1—O1	178.04 (6)	C7—C6—C5	121.7 (2)
Cr1—O1—H3	110.3	C7—C6—H9	119.1
Cr1—O1—H4	111.5	C5—C6—H9	119.1
H3—O1—H4	102.5	C6—C7—C10	119.2 (2)
Cr1—O2—H2	114.5	C6—C7—H6	120.4
Cr1—O2—H10	118.3	C10—C7—H6	120.4
H2—O2—H10	107.0	N1—C8—C5	118.0 (2)
C1—O3—Cr1	114.35 (12)	N1—C8—C9	116.9 (2)
C2—O4—Cr1	114.29 (13)	C5—C8—C9	125.1 (2)
C3—O5—Cr1	114.03 (12)	C8—C9—H8	109.5
C4—O6—Cr1	115.59 (13)	C8—C9—H14	109.5
H1—O11—H11	111.1	H8—C9—H14	109.5
C10—N1—C8	124.6 (2)	C8—C9—H15	109.5
C10—N1—H7	113.7	H8—C9—H15	109.5
C8—N1—H7	121.7	H14—C9—H15	109.5
C10—N2—H5	116.8	N2—C10—N1	118.7 (2)
C10—N2—H13	123.8	N2—C10—C7	123.7 (2)
H5—N2—H13	119.3	N1—C10—C7	117.6 (2)
O7—C1—O3	126.18 (18)
Cr1—O3—C1—O7	−177.14 (17)	O4—C2—C4—O9	−176.0 (2)
Cr1—O3—C1—C3	3.0 (2)	O10—C2—C4—O6	−174.65 (18)
Cr1—O4—C2—O10	176.81 (17)	O4—C2—C4—O6	4.3 (3)
Cr1—O4—C2—C4	−2.0 (2)	C8—C5—C6—C7	−0.3 (4)
Cr1—O5—C3—O8	−173.21 (18)	C5—C6—C7—C10	−0.5 (4)
Cr1—O5—C3—C1	6.1 (2)	C10—N1—C8—C5	−1.4 (4)
O7—C1—C3—O8	−6.7 (3)	C10—N1—C8—C9	178.2 (2)
O3—C1—C3—O8	173.12 (19)	C6—C5—C8—N1	1.2 (4)
O7—C1—C3—O5	173.94 (18)	C6—C5—C8—C9	−178.4 (3)
O3—C1—C3—O5	−6.2 (2)	C8—N1—C10—N2	−179.0 (2)
Cr1—O6—C4—O9	175.95 (19)	C8—N1—C10—C7	0.7 (4)
Cr1—O6—C4—C2	−4.4 (2)	C6—C7—C10—N2	−180.0 (2)
O10—C2—C4—O9	5.1 (3)	C6—C7—C10—N1	0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H3···O7i	0.83	1.82	2.643 (2)	171
O1—H4···O10ii	0.83	1.87	2.681 (2)	165
O2—H2···O11iii	0.83	1.78	2.611 (2)	173
O2—H10···O8iv	0.83	1.85	2.675 (2)	172
N1—H7···O9v	0.93	1.90	2.829 (2)	174
N2—H5···O7vi	0.93	2.16	2.928 (3)	139
N2—H13···O10v	0.93	2.08	2.976 (3)	162
C9—H8···O3iii	0.96	2.56	3.405 (3)	147
C9—H14···O5	0.96	2.64	3.277 (3)	124
O11—H1···O8i	0.83	2.17	2.983 (2)	167
O11—H11···O6	0.83	2.03	2.845 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H3⋯O7i	0.83	1.82	2.643 (2)	171
O1—H4⋯O10ii	0.83	1.87	2.681 (2)	165
O2—H2⋯O11iii	0.83	1.78	2.611 (2)	173
O2—H10⋯O8iv	0.83	1.85	2.675 (2)	172
N1—H7⋯O9v	0.93	1.90	2.829 (2)	174
N2—H5⋯O7vi	0.93	2.16	2.928 (3)	139
N2—H13⋯O10v	0.93	2.08	2.976 (3)	162
O11—H1⋯O8i	0.83	2.17	2.983 (2)	167
O11—H11⋯O6	0.83	2.03	2.845 (2)	169

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