3-Amino­pyridinium trans-diaqua­dioxalato­chromate(III)

Chérif, I.; Zid, M.F.; El-Ghozzi, M.; Avignant, D.

doi:10.1107/S1600536812025020

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages m900-m901

https://doi.org/10.1107/S1600536812025020

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3-Aminopyridinium trans-diaquadioxalatochromate(III)

Ichraf Chérif,^a ^* Mohamed Faouzi Zid,^a Malika El-Ghozzi ^b,^c and Daniel Avignant ^b,^c

^aLaboratoire de Matériaux et Cristallochimie, Faculté des Sciences de Tunis, Université de Tunis El Manar, 2092 Manar II Tunis, Tunisia, ^bClermont Université, Université Blaise Pascal, Institut de Chimie de Clermont-Ferrand, BP 10448, 63000 Clermont-Ferrand, France, and ^cCNRS, UMR 6296, ICCF, BP 80026, 63171 Aubière, France
^*Correspondence e-mail: cherif.ichraf@yahoo.fr

(Received 11 May 2012; accepted 1 June 2012; online 13 June 2012)

In the structure of the title compound, (C₅H₇N₂)[Cr(C₂O₄)₂(H₂O)₂], two crystallographically independent formula units are present. Both chromium atoms are six-coordinated in a distorted octahedral geometry by two chelating equatorial oxalato ligands and two axial water molecules. The [Cr(C₂O₄)₂(H₂O)₂]⁻ anions and C₅H₇N₂⁺ cations are linked through a complex three-dimensional hydrogen-bonding network consisting of N—H⋯O and O—H⋯O interactions.

Related literature

For the versatility of the oxalato ligand, see: Hernández-Molina et al. (2001 ); Martak et al. (2009 ); Marinescu et al. (2011 ). For magnetic studies of oxalatochromium (III) complexes, see: Chen et al. (2005 ); Marinescu et al. (2011). For complexes containing the [Cr(C₂O₄)₂(H₂O)₂]⁻ motif completed by various uncoordinated cations including quinolinium, 4-dimethylaminopyridinium and 4-aminopyridinium, see: Bélombé et al. (2009 ); Nenwa et al. (2010 ); Chérif et al. (2011 ).

Experimental

Crystal data

(C₅H₇N₂)[Cr(C₂O₄)₂(H₂O)₂]
M_r = 359.20
Monoclinic, P 2₁ /c
a = 7.3901 (15) Å
b = 17.586 (4) Å
c = 20.995 (5) Å
β = 107.941 (11)°
V = 2596.0 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 296 K
0.53 × 0.33 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.695, T_max = 0.835
22038 measured reflections
5865 independent reflections
4091 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.112
S = 1.04
5865 reflections
421 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected bond lengths (Å)

Cr1—O11	2.0223 (18)
Cr1—O12	2.0017 (17)
Cr1—O13	1.9421 (17)
Cr1—O14	1.9690 (18)
Cr1—O15	1.9771 (18)
Cr1—O16	1.9517 (18)
Cr2—O21	2.006 (2)
Cr2—O22	2.007 (2)
Cr2—O23	1.9604 (17)
Cr2—O24	1.9846 (18)
Cr2—O25	1.9429 (17)
Cr2—O26	1.9793 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11A⋯O25ⁱ	0.86	2.22	3.047 (4)	161
N11—H11B⋯O22ⁱⁱ	0.86	2.46	3.139 (4)	136
N12—H12⋯O18ⁱⁱⁱ	0.86	2.30	2.998 (3)	139
N12—H12⋯O20ⁱⁱⁱ	0.86	2.16	2.896 (3)	144
N21—H21A⋯O13^iv	0.86	2.31	3.142 (3)	163
N21—H21B⋯O11^v	0.86	2.42	3.201 (4)	151
N22—H22⋯O28^vi	0.86	2.38	3.121 (3)	145
N22—H22⋯O30^vi	0.86	2.05	2.755 (3)	138
O11—H111⋯O27^vii	0.84 (3)	2.30 (3)	3.103 (3)	161 (2)
O11—H111⋯O29^vii	0.84 (3)	2.19 (2)	2.749 (3)	123 (2)
O11—H211⋯O18^viii	0.84 (1)	1.95 (2)	2.777 (3)	173 (3)
O12—H112⋯O27	0.84 (2)	1.85 (2)	2.684 (3)	176 (2)
O12—H212⋯O28ⁱⁱ	0.84 (1)	1.78 (1)	2.619 (2)	172 (3)
O21—H121⋯O20ⁱⁱⁱ	0.84 (2)	1.85 (1)	2.682 (3)	176 (3)
O21—H221⋯O17^v	0.84 (2)	1.85 (2)	2.681 (3)	177 (2)
O22—H122⋯O23^ix	0.85 (2)	1.94 (2)	2.780 (2)	173 (3)
O22—H222⋯O19	0.84 (2)	1.85 (2)	2.646 (3)	157 (3)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1; (v) x-1, y, z; (vi) x, y+1, z; (vii) x+1, y, z; (viii) -x+2, -y+1, -z+1; (ix) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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, 1998 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812025020/vn2039sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025020/vn2039Isup2.hkl

checkCIF report

Comment top

In recent years, much work has been focused on the great versatility of the oxalato ligand which affords a wide number of homo and heteropolynuclear complexes with various dimensionalities and network architectures (Marinescu et al., 2011; Martak et al., 2009; Hernández-Molina et al., 2001). This exceptional versatility of the oxalato ligands offers possibilities for the tuning of magnetic properties and thus makes them very useful for obtaining materials with potential applications in magnetism (Chen et al., 2005; Marinescu et al., 2011). The present investigation deals with the new oxalato chromium (III) salt: (C₅H₇N₂)[Cr(C₂O₄)₂(H₂O)₂].

The structure is made up of two crystallographically independent entities of formula (C₅H₇N₂)[Cr(C₂O₄)₂(H₂O)₂] (Fig. 1). The two chromium atoms Cr1 and Cr2 exhibit a distorted octahedral environment with bond lengths and angles very close to each other. The Cr—O(ox) bonds ranges from 1.9421 (17) to 1.9771 (18) Å for Cr1—O(ox) and from 1.9429 (17) to 1.9846 (18) Å for Cr2—O(ox), values which are shorter than the Cr—O(water) bonds [2.0017 (17) - 2.0223 (18) Å for Cr1—O(water) and 2.006 (2) - 2.007 (2) Å for Cr2—O(water)]. Such type of coordination was already observed in complexes containing the [Cr(C₂O₄)₂(H₂O)₂]^- motif completed with various uncoordinated cations including quinolinium, 4-dimethylaminopyridinium and 4-aminopyridinium with similar geometric parameters (Bélombé et al., 2009; Nenwa et al., 2010; Chérif et al., 2011). The charge balance of the mononuclear anion is provided by an uncoordinated 3-aminopyridinium cation.

In the crystal structure intermolecular hydrogen bonds and very weak π—π contacts established between the 3-aminopyridinium cations connect the ionic entities generating layers parallel to (001) (Fig. 2). These layers are further connected by O—H···O [O11—H211···O18 / O12—H212···O28 / O21—H121···O20 / O22—H122···O23] and N—H···O [N11—H11A···O25 / N21—H21···O13] hydrogen bonds (Fig. 3). The shortest interlayer chromium (III) ion separations are: Cr1—Cr1: 5.808 (2) Å, Cr2—Cr2: 5.226 (2) Å and Cr1—Cr2: 6.301 (2) Å.

Related literature top

For the versatility of the oxalato ligand, see: Hernández-Molina et al. (2001); Martak et al. (2009); Marinescu et al. (2011). For magnetic studies of oxalatochromium (III) complexes, see: Chen et al. (2005); Marinescu et al. (2011). For complexes containing the [Cr(C₂O₄)₂(H₂O)₂]^- motif completed by various uncoordinated cations including quinolinium, 4-dimethylaminopyridinium and 4-aminopyridinium, see: Bélombé et al. (2009); Nenwa et al. (2010); Chérif et al. (2011).

Experimental top

To 10 cm³ of a solution of chromium chloride CrCl₃.6H₂O (1 mmol) was added under stirring at room temperature previously prepared solutions of 3-aminopyridine C₅H₆N₂ (1 mmol, 10 cm³) and oxalic acid H₂C₂O₄.2H₂O (2 mmol, 10 cm³) in water. The obtained solution was stirred for 3 h at 323 K and prismatic violet single crystals were grown by slow evaporation at room temperature.

Structure description top

For the versatility of the oxalato ligand, see: Hernández-Molina et al. (2001); Martak et al. (2009); Marinescu et al. (2011). For magnetic studies of oxalatochromium (III) complexes, see: Chen et al. (2005); Marinescu et al. (2011). For complexes containing the [Cr(C₂O₄)₂(H₂O)₂]^- motif completed by various uncoordinated cations including quinolinium, 4-dimethylaminopyridinium and 4-aminopyridinium, see: Bélombé et al. (2009); Nenwa et al. (2010); Chérif et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound with the atom-numbering scheme. Thermal ellipsoids are drawn at the 50% probability level for non-H atoms.
	Fig. 2. View of the hydrogen bonding system (dashed lines) and π—π stacking interactions between pairs of 3-aminopyridinium cations showing the layered structure.
	Fig. 3. Structure projection along a axis showing connection between layers via hydrogen bonds (dashed lines).

3-Aminopyridinium trans-diaquadioxalatochromate(III) top

Crystal data top

(C₅H₇N₂)[Cr(C₂O₄)₂(H₂O)₂]	F(000) = 1464
M_r = 359.20	D_x = 1.838 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5082 reflections
a = 7.3901 (15) Å	θ = 3.0–27.3°
b = 17.586 (4) Å	µ = 0.94 mm⁻¹
c = 20.995 (5) Å	T = 296 K
β = 107.941 (11)°	Prism, violet
V = 2596.0 (10) Å³	0.53 × 0.33 × 0.19 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	5865 independent reflections
Radiation source: fine-focus sealed tube	4091 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
T_min = 0.695, T_max = 0.835	k = −22→22
22038 measured reflections	l = −24→27

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0522P)² + 1.1562P] where P = (F_o² + 2F_c²)/3
5865 reflections	(Δ/σ)_max = 0.001
421 parameters	Δρ_max = 0.68 e Å⁻³
12 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

(C₅H₇N₂)[Cr(C₂O₄)₂(H₂O)₂]	V = 2596.0 (10) Å³
M_r = 359.20	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3901 (15) Å	µ = 0.94 mm⁻¹
b = 17.586 (4) Å	T = 296 K
c = 20.995 (5) Å	0.53 × 0.33 × 0.19 mm
β = 107.941 (11)°

Data collection top

Bruker APEXII CCD diffractometer	5865 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4091 reflections with I > 2σ(I)
T_min = 0.695, T_max = 0.835	R_int = 0.036
22038 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	12 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.68 e Å⁻³
5865 reflections	Δρ_min = −0.42 e Å⁻³
421 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cr1	0.86991 (5)	0.39632 (2)	0.387432 (18)	0.02059 (12)
O11	1.1473 (2)	0.39735 (10)	0.44297 (9)	0.0262 (4)
H111	1.205 (4)	0.3619 (12)	0.4303 (12)	0.039*
H211	1.160 (4)	0.3939 (15)	0.4838 (6)	0.039*
O12	0.5955 (2)	0.39686 (10)	0.33227 (8)	0.0265 (4)
H112	0.531 (3)	0.3644 (13)	0.3449 (12)	0.040*
H212	0.575 (4)	0.3931 (16)	0.2906 (5)	0.040*
O13	0.8080 (2)	0.33173 (10)	0.45283 (8)	0.0252 (4)
O14	0.9080 (2)	0.29864 (10)	0.34754 (8)	0.0276 (4)
O15	0.9201 (2)	0.46853 (10)	0.32268 (8)	0.0255 (4)
O16	0.8323 (2)	0.48926 (10)	0.43257 (8)	0.0252 (4)
O17	0.8865 (3)	0.17386 (11)	0.36410 (10)	0.0379 (5)
O18	0.8431 (3)	0.61488 (10)	0.42415 (9)	0.0320 (4)
O19	0.7775 (3)	0.21093 (10)	0.47675 (9)	0.0359 (5)
O20	0.9095 (3)	0.59268 (10)	0.30172 (9)	0.0304 (4)
C11	0.8736 (3)	0.24077 (15)	0.37920 (12)	0.0252 (6)
C12	0.8138 (3)	0.26020 (14)	0.44180 (12)	0.0228 (5)
C13	0.8984 (3)	0.53796 (14)	0.33634 (12)	0.0223 (5)
C14	0.8543 (3)	0.55075 (14)	0.40331 (12)	0.0228 (5)
Cr2	0.37874 (5)	0.07363 (2)	0.386675 (19)	0.02155 (12)
O21	0.1084 (3)	0.07383 (10)	0.32683 (9)	0.0272 (4)
H121	0.103 (4)	0.0772 (16)	0.2865 (6)	0.041*
H221	0.036 (3)	0.1047 (13)	0.3372 (12)	0.041*
O22	0.6505 (3)	0.07089 (10)	0.44535 (8)	0.0259 (4)
H122	0.663 (4)	0.0556 (14)	0.4848 (7)	0.039*
H222	0.704 (4)	0.1132 (9)	0.4470 (13)	0.039*
O23	0.3433 (2)	−0.02304 (9)	0.42779 (8)	0.0258 (4)
O24	0.4379 (2)	0.00638 (10)	0.31981 (8)	0.0270 (4)
O25	0.3026 (2)	0.13247 (10)	0.45248 (8)	0.0263 (4)
O26	0.4174 (2)	0.17523 (10)	0.35243 (9)	0.0288 (4)
O27	0.3779 (3)	0.29802 (11)	0.37330 (10)	0.0385 (5)
O28	0.4338 (3)	−0.11727 (10)	0.29469 (8)	0.0315 (4)
O29	0.2676 (3)	0.25175 (11)	0.48140 (10)	0.0375 (5)
O30	0.3577 (3)	−0.14718 (10)	0.41233 (9)	0.0404 (5)
C21	0.3098 (3)	0.20509 (15)	0.44561 (13)	0.0252 (6)
C22	0.3738 (3)	0.22954 (15)	0.38542 (13)	0.0267 (6)
C23	0.4178 (3)	−0.06459 (15)	0.33022 (11)	0.0227 (5)
C24	0.3688 (3)	−0.08241 (14)	0.39500 (12)	0.0246 (6)
N11	0.1544 (4)	0.41533 (17)	0.06676 (15)	0.0610 (8)
H11A	0.1725	0.3951	0.0319	0.073*
H11B	0.1520	0.4640	0.0704	0.073*
N12	0.1098 (3)	0.24902 (15)	0.15746 (14)	0.0446 (6)
H12	0.1131	0.2006	0.1524	0.053*
C1	0.1011 (4)	0.39996 (18)	0.17377 (15)	0.0418 (8)
H1	0.0967	0.4522	0.1799	0.050*
C2	0.0795 (5)	0.3528 (2)	0.22143 (17)	0.0523 (9)
H2	0.0636	0.3732	0.2602	0.063*
C3	0.0805 (4)	0.27507 (19)	0.21400 (16)	0.0485 (8)
H3	0.0619	0.2423	0.2462	0.058*
C4	0.1338 (4)	0.29243 (18)	0.10945 (16)	0.0402 (8)
H4	0.1532	0.2702	0.0719	0.048*
C5	0.1303 (4)	0.37163 (18)	0.11460 (15)	0.0396 (7)
N21	0.3221 (4)	0.56454 (17)	0.44750 (14)	0.0603 (8)
H21A	0.3077	0.5887	0.4812	0.072*
H21B	0.3170	0.5157	0.4464	0.072*
N22	0.3907 (3)	0.71990 (14)	0.34738 (13)	0.0405 (6)
H22	0.3952	0.7687	0.3499	0.049*
C6	0.3605 (4)	0.68177 (17)	0.39823 (15)	0.0359 (7)
H6	0.3450	0.7080	0.4346	0.043*
C7	0.4141 (4)	0.68807 (19)	0.29359 (16)	0.0454 (8)
H7	0.4340	0.7173	0.2595	0.055*
C8	0.4078 (4)	0.6097 (2)	0.28982 (15)	0.0464 (8)
H8	0.4236	0.5853	0.2526	0.056*
C9	0.3789 (4)	0.56839 (17)	0.34007 (16)	0.0412 (7)
H9	0.3767	0.5156	0.3370	0.049*
C10	0.3523 (4)	0.60299 (17)	0.39666 (15)	0.0350 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cr1	0.0306 (2)	0.0155 (2)	0.0179 (2)	−0.00071 (16)	0.01067 (16)	0.00029 (15)
O11	0.0333 (10)	0.0199 (10)	0.0251 (9)	0.0027 (8)	0.0085 (8)	−0.0015 (7)
O12	0.0326 (10)	0.0269 (10)	0.0212 (9)	−0.0032 (8)	0.0100 (8)	0.0025 (8)
O13	0.0388 (10)	0.0196 (9)	0.0211 (9)	−0.0010 (8)	0.0149 (8)	−0.0010 (7)
O14	0.0389 (10)	0.0231 (10)	0.0253 (9)	−0.0014 (8)	0.0163 (8)	−0.0023 (8)
O15	0.0373 (10)	0.0200 (10)	0.0227 (9)	0.0000 (8)	0.0144 (8)	0.0008 (7)
O16	0.0383 (10)	0.0201 (9)	0.0206 (9)	0.0001 (8)	0.0142 (8)	−0.0006 (7)
O17	0.0400 (11)	0.0233 (11)	0.0496 (12)	0.0021 (9)	0.0129 (9)	−0.0104 (9)
O18	0.0489 (11)	0.0189 (10)	0.0288 (10)	0.0010 (8)	0.0128 (9)	−0.0030 (8)
O19	0.0536 (12)	0.0226 (10)	0.0324 (11)	−0.0083 (9)	0.0148 (9)	0.0037 (8)
O20	0.0459 (11)	0.0210 (10)	0.0247 (10)	−0.0048 (8)	0.0116 (8)	0.0041 (8)
C11	0.0212 (13)	0.0257 (15)	0.0268 (13)	−0.0005 (11)	0.0043 (10)	−0.0032 (11)
C12	0.0237 (12)	0.0203 (14)	0.0224 (12)	−0.0013 (10)	0.0041 (10)	0.0004 (10)
C13	0.0232 (12)	0.0211 (13)	0.0210 (12)	−0.0027 (10)	0.0046 (10)	0.0002 (10)
C14	0.0247 (13)	0.0206 (14)	0.0204 (12)	0.0005 (10)	0.0030 (10)	0.0001 (10)
Cr2	0.0317 (2)	0.0164 (2)	0.0186 (2)	0.00061 (16)	0.01077 (17)	0.00100 (15)
O21	0.0335 (10)	0.0263 (10)	0.0230 (9)	0.0036 (8)	0.0102 (8)	−0.0026 (8)
O22	0.0352 (10)	0.0178 (9)	0.0247 (9)	−0.0015 (8)	0.0092 (8)	0.0025 (7)
O23	0.0392 (10)	0.0200 (10)	0.0212 (9)	−0.0015 (8)	0.0139 (8)	−0.0004 (7)
O24	0.0387 (10)	0.0258 (10)	0.0208 (9)	0.0008 (8)	0.0157 (8)	0.0000 (7)
O25	0.0385 (10)	0.0197 (9)	0.0233 (9)	0.0011 (8)	0.0133 (8)	0.0005 (7)
O26	0.0370 (10)	0.0247 (10)	0.0273 (10)	0.0011 (8)	0.0138 (8)	0.0069 (8)
O27	0.0391 (11)	0.0206 (10)	0.0539 (13)	−0.0015 (9)	0.0114 (10)	0.0111 (9)
O28	0.0457 (11)	0.0267 (11)	0.0231 (9)	0.0063 (8)	0.0119 (8)	−0.0056 (8)
O29	0.0495 (12)	0.0260 (11)	0.0393 (11)	0.0064 (9)	0.0168 (9)	−0.0068 (9)
O30	0.0722 (14)	0.0195 (11)	0.0342 (11)	−0.0016 (10)	0.0234 (10)	0.0006 (8)
C21	0.0230 (13)	0.0220 (14)	0.0275 (13)	0.0017 (11)	0.0032 (10)	−0.0010 (11)
C22	0.0233 (13)	0.0239 (14)	0.0298 (14)	0.0007 (11)	0.0037 (11)	0.0053 (11)
C23	0.0256 (13)	0.0244 (14)	0.0168 (12)	0.0034 (10)	0.0045 (10)	0.0009 (10)
C24	0.0312 (14)	0.0198 (14)	0.0224 (13)	−0.0002 (11)	0.0077 (11)	−0.0013 (10)
N11	0.091 (2)	0.0408 (17)	0.063 (2)	−0.0057 (16)	0.0408 (18)	−0.0036 (15)
N12	0.0458 (15)	0.0305 (14)	0.0538 (17)	0.0036 (12)	0.0100 (13)	−0.0005 (13)
C1	0.0465 (18)	0.0302 (16)	0.0490 (19)	0.0060 (14)	0.0154 (15)	−0.0161 (14)
C2	0.057 (2)	0.058 (2)	0.047 (2)	0.0019 (18)	0.0239 (16)	−0.0090 (17)
C3	0.0514 (19)	0.045 (2)	0.047 (2)	0.0028 (16)	0.0122 (16)	−0.0084 (16)
C4	0.0322 (15)	0.0386 (19)	0.0459 (18)	0.0040 (13)	0.0063 (13)	−0.0226 (15)
C5	0.0374 (16)	0.0363 (18)	0.0443 (18)	0.0008 (13)	0.0113 (14)	0.0005 (14)
N21	0.087 (2)	0.0436 (18)	0.065 (2)	−0.0002 (15)	0.0444 (17)	0.0071 (15)
N22	0.0423 (14)	0.0288 (14)	0.0484 (16)	−0.0035 (11)	0.0108 (12)	−0.0017 (12)
C6	0.0349 (15)	0.0326 (17)	0.0402 (17)	0.0000 (13)	0.0114 (13)	−0.0127 (13)
C7	0.0472 (18)	0.051 (2)	0.0379 (18)	−0.0001 (16)	0.0129 (15)	0.0033 (15)
C8	0.0449 (18)	0.060 (2)	0.0375 (18)	0.0007 (16)	0.0169 (14)	−0.0205 (16)
C9	0.0388 (17)	0.0286 (16)	0.056 (2)	0.0046 (13)	0.0140 (15)	−0.0146 (15)
C10	0.0307 (15)	0.0317 (16)	0.0446 (18)	0.0006 (12)	0.0143 (13)	−0.0036 (13)

Geometric parameters (Å, º) top

Cr1—O11	2.0223 (18)	O22—H122	0.848 (16)
Cr1—O12	2.0017 (17)	O22—H222	0.84 (2)
Cr1—O13	1.9421 (17)	N11—C5	1.320 (4)
Cr1—O14	1.9690 (18)	N12—C3	1.351 (4)
Cr1—O15	1.9771 (18)	N12—C4	1.319 (4)
Cr1—O16	1.9517 (18)	N11—H11B	0.8600
Cr2—O21	2.006 (2)	N11—H11A	0.8600
Cr2—O22	2.007 (2)	N12—H12	0.8600
Cr2—O23	1.9604 (17)	N21—C10	1.339 (4)
Cr2—O24	1.9846 (18)	N22—C6	1.336 (4)
Cr2—O25	1.9429 (17)	N22—C7	1.319 (4)
Cr2—O26	1.9793 (18)	N21—H21A	0.8600
O13—C12	1.282 (3)	N21—H21B	0.8600
O14—C11	1.283 (3)	N22—H22	0.8600
O15—C13	1.276 (3)	C11—C12	1.548 (3)
O16—C14	1.279 (3)	C13—C14	1.554 (3)
O17—C11	1.230 (3)	C21—C22	1.541 (4)
O18—C14	1.222 (3)	C23—C24	1.544 (3)
O19—C12	1.218 (3)	C1—C2	1.347 (5)
O20—C13	1.224 (3)	C1—C5	1.415 (4)
O11—H211	0.835 (13)	C2—C3	1.376 (5)
O11—H111	0.84 (3)	C4—C5	1.398 (4)
O12—H212	0.843 (11)	C1—H1	0.9300
O12—H112	0.84 (2)	C2—H2	0.9300
O23—C24	1.296 (3)	C3—H3	0.9300
O24—C23	1.284 (3)	C4—H4	0.9300
O25—C21	1.288 (3)	C6—C10	1.387 (4)
O26—C22	1.278 (3)	C7—C8	1.380 (5)
O27—C22	1.233 (3)	C8—C9	1.351 (4)
O28—C23	1.218 (3)	C9—C10	1.402 (4)
O29—C21	1.216 (3)	C6—H6	0.9300
O30—C24	1.206 (3)	C7—H7	0.9300
O21—H121	0.837 (15)	C8—H8	0.9300
O21—H221	0.84 (2)	C9—H9	0.9300

Cr1···O28ⁱ	3.7984 (19)	O19···H122	2.88 (3)
Cr2···O19	3.829 (2)	O19···H6ⁱⁱ	2.7100
Cr1···H21Aⁱⁱ	3.4100	O19···H222	1.852 (18)
Cr1···H2ⁱⁱⁱ	3.4200	O19···H4^vi	2.9000
O11···O14	2.824 (3)	O20···H12ⁱ	2.1600
O11···O15	2.855 (2)	O20···H121ⁱ	1.846 (15)
O11···O13	2.825 (2)	O20···H3ⁱ	2.8500
O11···O27ⁱⁱⁱ	3.103 (3)	O21···H1^xi	2.6000
O11···O29ⁱⁱⁱ	2.749 (3)	O22···H11B^v	2.4600
O11···N21ⁱⁱⁱ	3.201 (4)	O23···H122	2.68 (3)
O11···C14	3.398 (3)	O23···H122^vii	1.937 (17)
O11···O16	2.787 (2)	O24···H8^v	2.5000
O11···O18^iv	2.777 (3)	O24···H121	2.66 (3)
O11···C14^iv	3.358 (3)	O25···H11A^ix	2.2200
O12···O27	2.684 (3)	O25···H122	2.88 (3)
O12···O14	2.822 (2)	O25···H221	2.65 (2)
O12···O15	2.772 (2)	O26···H121	2.88 (3)
O12···O13	2.781 (2)	O26···H222	2.65 (3)
O12···O28ⁱ	2.619 (2)	O27···H112	1.85 (2)
O12···C11	3.389 (3)	O27···H111^viii	2.30 (3)
O12···C12	3.374 (3)	O28···H212^v	1.781 (13)
O12···C13	3.325 (3)	O28···H22^x	2.3800
O12···C14	3.384 (3)	O29···H211^viii	2.63 (3)
O12···O16	2.805 (2)	O29···H4^ix	2.3400
O13···C11	2.376 (3)	O29···H111^viii	2.19 (2)
O13···O12	2.781 (2)	O30···H22^x	2.0500
O13···O18^iv	3.178 (3)	O30···H6^x	2.6000
O13···O14	2.603 (2)	O30···H122^vii	2.74 (2)
O13···O16	2.817 (3)	N11···O22ⁱ	3.139 (4)
O13···O27	3.158 (3)	N11···C23ⁱ	3.254 (4)
O13···N21ⁱⁱ	3.142 (3)	N11···C24ⁱ	3.364 (4)
O13···O11	2.825 (2)	N11···O25^xii	3.047 (4)
O14···O13	2.603 (2)	N12···O20^v	2.896 (3)
O14···C12	2.389 (3)	N12···O18^v	2.998 (3)
O14···O12	2.822 (2)	N21···O11^viii	3.201 (4)
O14···O15	3.039 (3)	N21···C13^viii	3.312 (4)
O14···O11	2.824 (3)	N21···C14^viii	3.301 (4)
O14···C2ⁱⁱⁱ	3.405 (4)	N21···O13ⁱⁱ	3.142 (3)
O15···C2ⁱⁱⁱ	3.405 (4)	N21···O16ⁱⁱ	3.211 (3)
O15···O12	2.772 (2)	N22···O30^xiii	2.755 (3)
O15···O11	2.855 (2)	N22···O28^xiii	3.121 (3)
O15···C14	2.388 (3)	C1···O28ⁱ	3.308 (4)
O15···O16	2.608 (2)	C1···O30^xiv	3.417 (4)
O15···O14	3.039 (3)	C1···C24^xiv	3.339 (4)
O16···C13	2.380 (3)	C2···O27	3.410 (4)
O16···O11	2.787 (2)	C2···O15^viii	3.405 (4)
O16···N21ⁱⁱ	3.211 (3)	C2···O14^viii	3.405 (4)
O16···O12	2.805 (2)	C3···O27	3.413 (4)
O16···O16^iv	3.159 (2)	C3···O20^v	3.228 (4)
O16···O15	2.608 (2)	C4···O18^v	3.217 (4)
O16···O13	2.817 (3)	C4···O19^xv	3.191 (4)
O17···O25ⁱⁱⁱ	3.149 (3)	C4···O29^xii	3.232 (4)
O17···O21ⁱⁱⁱ	2.681 (3)	C5···O28ⁱ	3.204 (4)
O17···O19	2.800 (3)	C5···C23ⁱ	3.372 (4)
O17···C21ⁱⁱⁱ	3.117 (3)	C6···O30^xiii	3.023 (4)
O17···C7^v	3.380 (4)	C6···O29ⁱⁱ	3.321 (4)
O18···O13^iv	3.178 (3)	C7···O17ⁱ	3.380 (4)
O18···O11^iv	2.777 (3)	C8···O24ⁱ	3.394 (4)
O18···O20	2.789 (3)	C8···C14	3.577 (4)
O18···C4ⁱ	3.217 (4)	C9···C14	3.366 (4)
O18···N12ⁱ	2.998 (3)	C9···C13^viii	3.568 (4)
O19···O26	3.164 (3)	C9···O20^viii	3.338 (4)
O19···O22	2.646 (3)	C10···O20^viii	3.270 (4)
O19···C22	3.027 (3)	C10···C13^viii	3.398 (4)
O19···C21	3.315 (3)	C11···O29ⁱⁱⁱ	3.045 (3)
O19···C4^vi	3.191 (4)	C11···C21ⁱⁱⁱ	3.156 (3)
O19···O17	2.800 (3)	C12···C22	3.145 (3)
O19···O30^vii	3.019 (3)	C12···O26	3.309 (3)
O19···Cr2	3.829 (2)	C12···O29ⁱⁱⁱ	3.200 (3)
O20···N12ⁱ	2.896 (3)	C12···O27	3.168 (3)
O20···O21ⁱ	2.682 (3)	C13···N21ⁱⁱⁱ	3.312 (4)
O20···C3ⁱ	3.228 (4)	C13···C10ⁱⁱⁱ	3.398 (4)
O20···O18	2.789 (3)	C13···C9ⁱⁱⁱ	3.568 (4)
O20···C10ⁱⁱⁱ	3.270 (4)	C14···O11^iv	3.358 (3)
O20···C9ⁱⁱⁱ	3.338 (4)	C14···C9	3.366 (4)
O21···C24	3.407 (3)	C14···C8	3.577 (4)
O21···O20^v	2.682 (3)	C14···N21ⁱⁱⁱ	3.301 (4)
O21···C23	3.325 (3)	C21···C11^viii	3.156 (3)
O21···O17^viii	2.681 (3)	C21···O30^vii	3.385 (3)
O21···O25	2.784 (3)	C21···O19	3.315 (3)
O21···O24	2.753 (3)	C21···O17^viii	3.117 (3)
O21···O23	2.853 (3)	C22···C12	3.145 (3)
O21···C21	3.388 (3)	C22···O19	3.027 (3)
O21···O26	2.816 (3)	C23···C5^v	3.372 (4)
O21···C22	3.372 (3)	C23···N11^v	3.254 (4)
O22···O23	2.739 (3)	C24···C1^xi	3.339 (4)
O22···C24	3.371 (3)	C24···N11^v	3.364 (4)
O22···O26	2.841 (3)	C24···O22^vii	3.405 (3)
O22···C24^vii	3.405 (3)	C11···H221ⁱⁱⁱ	2.93 (2)
O22···N11^v	3.139 (4)	C12···H112	3.04 (2)
O22···O19	2.646 (3)	C12···H222	2.722 (18)
O22···O25	2.836 (3)	C13···H121ⁱ	2.667 (16)
O22···O23^vii	2.780 (2)	C13···H12ⁱ	2.8700
O22···O24	2.855 (2)	C14···H12ⁱ	2.9200
O23···O24	2.622 (2)	C14···H211^iv	2.594 (17)
O23···O22^vii	2.780 (2)	C21···H221	3.09 (2)
O23···O22	2.739 (3)	C21···H11A^ix	2.9200
O23···C23	2.393 (3)	C21···H111^viii	2.86 (2)
O23···O25	2.817 (2)	C22···H112	2.88 (2)
O23···O21	2.853 (3)	C22···H111^viii	2.93 (2)
O24···O21	2.753 (3)	C23···H22^x	2.9700
O24···O26	3.062 (3)	C23···H212^v	2.660 (15)
O24···C24	2.385 (3)	C24···H122^vii	2.648 (18)
O24···C8^v	3.394 (4)	C24···H22^x	2.8100
O24···O23	2.622 (2)	H1···H11B	2.4600
O24···O22	2.855 (2)	H1···O21^xiv	2.6000
O25···N11^ix	3.047 (4)	H2···O15^viii	2.5500
O25···O21	2.784 (3)	H2···O14^viii	2.7800
O25···O30^vii	3.168 (3)	H2···Cr1^viii	3.4200
O25···O23	2.817 (2)	H3···O20^v	2.8500
O25···O22	2.836 (3)	H3···O14^viii	2.8800
O25···O26	2.607 (2)	H4···O18^v	2.7300
O25···O17^viii	3.149 (3)	H4···H11A	2.3700
O25···C22	2.373 (3)	H4···O29^xii	2.3400
O26···O22	2.841 (3)	H4···O19^xv	2.9000
O26···O25	2.607 (2)	H6···H21A	2.3700
O26···O24	3.062 (3)	H6···O30^xiii	2.6000
O26···C21	2.386 (3)	H6···O19ⁱⁱ	2.7100
O26···O19	3.164 (3)	H8···O24ⁱ	2.5000
O26···O21	2.816 (3)	H9···H21B	2.4700
O26···C12	3.309 (3)	H9···O12	2.6600
O27···C3	3.413 (4)	H11A···H4	2.3700
O27···C12	3.168 (3)	H11A···O25^xii	2.2200
O27···O13	3.158 (3)	H11A···C21^xii	2.9200
O27···O29	2.760 (3)	H11B···O22ⁱ	2.4600
O27···O12	2.684 (3)	H11B···H1	2.4600
O27···C2	3.410 (4)	H12···C13^v	2.8700
O27···O11^viii	3.103 (3)	H12···C14^v	2.9200
O28···O30	2.748 (3)	H12···O18^v	2.3000
O28···C5^v	3.204 (4)	H12···O20^v	2.1600
O28···O12^v	2.619 (2)	H21A···Cr1ⁱⁱ	3.4100
O28···N22^x	3.121 (3)	H21A···O16ⁱⁱ	2.7200
O28···Cr1^v	3.7984 (19)	H21A···O13ⁱⁱ	2.3100
O28···C1^v	3.308 (4)	H21A···H6	2.3700
O29···C6ⁱⁱ	3.321 (4)	H21B···H9	2.4700
O29···C12^viii	3.200 (3)	H21B···O11^viii	2.4200
O29···C11^viii	3.045 (3)	H22···O30^xiii	2.0500
O29···C4^ix	3.232 (4)	H22···C23^xiii	2.9700
O29···O27	2.760 (3)	H22···O28^xiii	2.3800
O29···O11^viii	2.749 (3)	H22···C24^xiii	2.8100
O30···O19^vii	3.019 (3)	H111···C21ⁱⁱⁱ	2.86 (2)
O30···O28	2.748 (3)	H111···C22ⁱⁱⁱ	2.93 (2)
O30···C1^xi	3.417 (4)	H111···O29ⁱⁱⁱ	2.19 (2)
O30···N22^x	2.755 (3)	H111···O27ⁱⁱⁱ	2.30 (3)
O30···C21^vii	3.385 (3)	H112···O27	1.85 (2)
O30···O25^vii	3.168 (3)	H112···C12	3.04 (2)
O30···C6^x	3.023 (4)	H112···C22	2.88 (2)
O11···H21Bⁱⁱⁱ	2.4200	H121···O20^v	1.846 (14)
O12···H9	2.6600	H121···C13^v	2.667 (16)
O13···H21Aⁱⁱ	2.3100	H122···O30^vii	2.74 (2)
O13···H211	2.71 (3)	H122···C24^vii	2.648 (18)
O13···H112	2.61 (2)	H122···O19	2.88 (3)
O14···H212	2.90 (3)	H122···O23^vii	1.937 (18)
O14···H111	2.59 (3)	H211···C14^iv	2.594 (17)
O14···H3ⁱⁱⁱ	2.8800	H211···O29ⁱⁱⁱ	2.63 (3)
O14···H2ⁱⁱⁱ	2.7800	H211···O18^iv	1.946 (15)
O15···H212	2.77 (3)	H211···O16^iv	2.69 (2)
O15···H2ⁱⁱⁱ	2.5500	H212···O28ⁱ	1.781 (13)
O16···H211	2.87 (3)	H212···C23ⁱ	2.660 (15)
O16···H211^iv	2.69 (2)	H221···C11^viii	2.93 (2)
O16···H21Aⁱⁱ	2.7200	H221···C21	3.09 (2)
O17···H221ⁱⁱⁱ	1.85 (2)	H221···O17^viii	1.85 (2)
O17···H222	2.73 (3)	H222···C12	2.722 (18)
O18···H12ⁱ	2.3000	H222···O17	2.73 (3)
O18···H211^iv	1.946 (15)	H222···O19	1.852 (18)
O18···H4ⁱ	2.7300

O11—Cr1—O12	179.21 (7)	H21A—N21—H21B	120.00
O11—Cr1—O13	90.88 (7)	C10—N21—H21A	120.00
O11—Cr1—O14	90.04 (7)	C7—N22—H22	118.00
O11—Cr1—O15	91.10 (7)	C6—N22—H22	118.00
O11—Cr1—O16	89.04 (7)	O17—C11—C12	119.7 (2)
O12—Cr1—O13	89.69 (7)	O14—C11—O17	125.6 (2)
O12—Cr1—O14	90.58 (7)	O14—C11—C12	114.8 (2)
O12—Cr1—O15	88.30 (7)	O13—C12—C11	113.8 (2)
O12—Cr1—O16	90.37 (7)	O19—C12—C11	121.9 (2)
O13—Cr1—O14	83.46 (7)	O13—C12—O19	124.3 (2)
O13—Cr1—O15	175.36 (7)	O15—C13—C14	114.7 (2)
O13—Cr1—O16	92.68 (7)	O15—C13—O20	125.7 (2)
O14—Cr1—O15	100.73 (7)	O20—C13—C14	119.6 (2)
O14—Cr1—O16	176.02 (7)	O16—C14—C13	113.9 (2)
O15—Cr1—O16	83.16 (7)	O16—C14—O18	125.2 (2)
O23—Cr2—O24	83.29 (7)	O18—C14—C13	120.9 (2)
O23—Cr2—O25	92.38 (7)	O25—C21—C22	113.7 (2)
O23—Cr2—O26	175.27 (7)	O25—C21—O29	124.9 (2)
O24—Cr2—O25	174.57 (7)	O29—C21—C22	121.4 (2)
O24—Cr2—O26	101.13 (7)	O27—C22—C21	118.4 (2)
O25—Cr2—O26	83.30 (7)	O26—C22—O27	126.3 (2)
O22—Cr2—O24	91.32 (7)	O26—C22—C21	115.4 (2)
O21—Cr2—O22	178.47 (8)	O28—C23—C24	118.6 (2)
O21—Cr2—O23	92.00 (7)	O24—C23—C24	114.7 (2)
O21—Cr2—O24	87.24 (7)	O24—C23—O28	126.7 (2)
O21—Cr2—O25	89.64 (7)	O23—C24—C23	114.6 (2)
O21—Cr2—O26	89.90 (7)	O23—C24—O30	124.5 (2)
O22—Cr2—O23	87.31 (7)	O30—C24—C23	120.9 (2)
O22—Cr2—O25	91.75 (7)	C2—C1—C5	121.4 (3)
O22—Cr2—O26	90.89 (7)	C1—C2—C3	121.4 (3)
Cr1—O13—C12	114.70 (15)	N12—C3—C2	116.4 (3)
Cr1—O14—C11	113.24 (15)	N12—C4—C5	120.5 (3)
Cr1—O15—C13	113.39 (15)	C1—C5—C4	115.5 (3)
Cr1—O16—C14	114.63 (15)	N11—C5—C1	123.8 (3)
Cr1—O11—H211	111 (2)	N11—C5—C4	120.8 (3)
H111—O11—H211	111 (3)	C2—C1—H1	119.00
Cr1—O11—H111	109.4 (18)	C5—C1—H1	119.00
H112—O12—H212	110 (3)	C1—C2—H2	119.00
Cr1—O12—H212	115 (2)	C3—C2—H2	119.00
Cr1—O12—H112	112.8 (16)	C2—C3—H3	122.00
Cr2—O23—C24	113.81 (15)	N12—C3—H3	122.00
Cr2—O24—C23	113.37 (14)	C5—C4—H4	120.00
Cr2—O25—C21	114.67 (15)	N12—C4—H4	120.00
Cr2—O26—C22	112.90 (16)	N22—C6—C10	119.9 (3)
H121—O21—H221	113 (3)	N22—C7—C8	117.5 (3)
Cr2—O21—H221	115.6 (16)	C7—C8—C9	120.2 (3)
Cr2—O21—H121	111 (2)	C8—C9—C10	121.7 (3)
H122—O22—H222	109 (2)	N21—C10—C9	123.9 (3)
Cr2—O22—H122	113 (2)	C6—C10—C9	115.9 (3)
Cr2—O22—H222	112.0 (18)	N21—C10—C6	120.2 (3)
C3—N12—C4	124.8 (3)	N22—C6—H6	120.00
H11A—N11—H11B	120.00	C10—C6—H6	120.00
C5—N11—H11A	120.00	N22—C7—H7	121.00
C5—N11—H11B	120.00	C8—C7—H7	121.00
C4—N12—H12	118.00	C7—C8—H8	120.00
C3—N12—H12	118.00	C9—C8—H8	120.00
C6—N22—C7	124.7 (3)	C8—C9—H9	119.00
C10—N21—H21B	120.00	C10—C9—H9	119.00

O11—Cr1—O13—C12	−91.40 (16)	Cr2—O23—C24—C23	−1.1 (2)
O12—Cr1—O13—C12	89.16 (16)	Cr2—O23—C24—O30	178.4 (2)
O14—Cr1—O13—C12	−1.46 (16)	Cr2—O24—C23—O28	175.3 (2)
O16—Cr1—O13—C12	179.52 (16)	Cr2—O24—C23—C24	−4.8 (2)
O11—Cr1—O14—C11	92.22 (16)	Cr2—O25—C21—C22	1.2 (2)
O12—Cr1—O14—C11	−88.28 (16)	Cr2—O25—C21—O29	179.8 (2)
O13—Cr1—O14—C11	1.34 (16)	Cr2—O26—C22—C21	2.5 (3)
O15—Cr1—O14—C11	−176.66 (15)	Cr2—O26—C22—O27	−177.3 (2)
O11—Cr1—O15—C13	−91.84 (16)	C3—N12—C4—C5	0.1 (5)
O12—Cr1—O15—C13	87.64 (16)	C4—N12—C3—C2	−1.2 (5)
O14—Cr1—O15—C13	177.91 (15)	C7—N22—C6—C10	0.1 (5)
O16—Cr1—O15—C13	−2.94 (16)	C6—N22—C7—C8	−0.3 (5)
O11—Cr1—O16—C14	91.27 (16)	O17—C11—C12—O19	−0.5 (4)
O12—Cr1—O16—C14	−88.20 (16)	O14—C11—C12—O13	−0.2 (3)
O13—Cr1—O16—C14	−177.90 (16)	O17—C11—C12—O13	179.1 (2)
O15—Cr1—O16—C14	0.05 (16)	O14—C11—C12—O19	−179.7 (2)
O25—Cr2—O26—C22	−1.51 (16)	O15—C13—C14—O18	175.1 (2)
O21—Cr2—O23—C24	85.88 (16)	O20—C13—C14—O18	−4.9 (4)
O22—Cr2—O23—C24	−92.75 (16)	O15—C13—C14—O16	−4.9 (3)
O24—Cr2—O23—C24	−1.11 (15)	O20—C13—C14—O16	175.1 (2)
O25—Cr2—O23—C24	175.60 (16)	O25—C21—C22—O26	−2.5 (3)
O21—Cr2—O24—C23	−88.89 (16)	O29—C21—C22—O26	178.8 (2)
O22—Cr2—O24—C23	90.59 (16)	O29—C21—C22—O27	−1.4 (4)
O23—Cr2—O24—C23	3.45 (15)	O25—C21—C22—O27	177.2 (2)
O26—Cr2—O24—C23	−178.25 (15)	O28—C23—C24—O30	4.4 (4)
O21—Cr2—O25—C21	−89.89 (16)	O28—C23—C24—O23	−176.1 (2)
O22—Cr2—O25—C21	90.74 (16)	O24—C23—C24—O30	−175.5 (2)
O23—Cr2—O25—C21	178.12 (16)	O24—C23—C24—O23	4.0 (3)
O26—Cr2—O25—C21	0.05 (17)	C5—C1—C2—C3	−1.5 (5)
O21—Cr2—O26—C22	88.14 (17)	C2—C1—C5—C4	0.3 (5)
O22—Cr2—O26—C22	−93.17 (17)	C2—C1—C5—N11	−179.2 (3)
O24—Cr2—O26—C22	175.31 (16)	C1—C2—C3—N12	1.9 (5)
Cr1—O13—C12—C11	1.3 (2)	N12—C4—C5—N11	179.9 (3)
Cr1—O13—C12—O19	−179.2 (2)	N12—C4—C5—C1	0.4 (4)
Cr1—O14—C11—C12	−1.0 (2)	N22—C6—C10—N21	180.0 (3)
Cr1—O14—C11—O17	179.8 (2)	N22—C6—C10—C9	0.5 (4)
Cr1—O15—C13—O20	−175.2 (2)	N22—C7—C8—C9	−0.1 (5)
Cr1—O15—C13—C14	4.8 (2)	C7—C8—C9—C10	0.8 (5)
Cr1—O16—C14—C13	2.4 (2)	C8—C9—C10—N21	179.6 (3)
Cr1—O16—C14—O18	−177.6 (2)	C8—C9—C10—C6	−1.0 (5)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+1, −z+1; (v) −x+1, y−1/2, −z+1/2; (vi) x+1, −y+1/2, z+1/2; (vii) −x+1, −y, −z+1; (viii) x−1, y, z; (ix) x, −y+1/2, z+1/2; (x) x, y−1, z; (xi) −x, y−1/2, −z+1/2; (xii) x, −y+1/2, z−1/2; (xiii) x, y+1, z; (xiv) −x, y+1/2, −z+1/2; (xv) x−1, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···O25^xii	0.86	2.22	3.047 (4)	161
N11—H11B···O22ⁱ	0.86	2.46	3.139 (4)	136
N12—H12···O18^v	0.86	2.30	2.998 (3)	139
N12—H12···O20^v	0.86	2.16	2.896 (3)	144
N21—H21A···O13ⁱⁱ	0.86	2.31	3.142 (3)	163
N21—H21B···O11^viii	0.86	2.42	3.201 (4)	151
N22—H22···O28^xiii	0.86	2.38	3.121 (3)	145
N22—H22···O30^xiii	0.86	2.05	2.755 (3)	138
O11—H111···O27ⁱⁱⁱ	0.84 (3)	2.30 (3)	3.103 (3)	161 (2)
O11—H111···O29ⁱⁱⁱ	0.84 (3)	2.19 (2)	2.749 (3)	123 (2)
O11—H211···O18^iv	0.84 (1)	1.95 (2)	2.777 (3)	173 (3)
O12—H112···O27	0.84 (2)	1.85 (2)	2.684 (3)	176 (2)
O12—H212···O28ⁱ	0.84 (1)	1.78 (1)	2.619 (2)	172 (3)
O21—H121···O20^v	0.84 (2)	1.85 (1)	2.682 (3)	176 (3)
O21—H221···O17^viii	0.84 (2)	1.85 (2)	2.681 (3)	177 (2)
O22—H122···O23^vii	0.85 (2)	1.94 (2)	2.780 (2)	173 (3)
O22—H222···O19	0.84 (2)	1.85 (2)	2.646 (3)	157 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+1, −z+1; (v) −x+1, y−1/2, −z+1/2; (vii) −x+1, −y, −z+1; (viii) x−1, y, z; (xii) x, −y+1/2, z−1/2; (xiii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	(C₅H₇N₂)[Cr(C₂O₄)₂(H₂O)₂]
M_r	359.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.3901 (15), 17.586 (4), 20.995 (5)
β (°)	107.941 (11)
V (Å³)	2596.0 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.53 × 0.33 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.695, 0.835
No. of measured, independent and observed [I > 2σ(I)] reflections	22038, 5865, 4091
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.112, 1.04
No. of reflections	5865
No. of parameters	421
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.42

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cr1—O11	2.0223 (18)	Cr2—O21	2.006 (2)
Cr1—O12	2.0017 (17)	Cr2—O22	2.007 (2)
Cr1—O13	1.9421 (17)	Cr2—O23	1.9604 (17)
Cr1—O14	1.9690 (18)	Cr2—O24	1.9846 (18)
Cr1—O15	1.9771 (18)	Cr2—O25	1.9429 (17)
Cr1—O16	1.9517 (18)	Cr2—O26	1.9793 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···O25ⁱ	0.8600	2.2200	3.047 (4)	161.00
N11—H11B···O22ⁱⁱ	0.8600	2.4600	3.139 (4)	136.00
N12—H12···O18ⁱⁱⁱ	0.8600	2.3000	2.998 (3)	139.00
N12—H12···O20ⁱⁱⁱ	0.8600	2.1600	2.896 (3)	144.00
N21—H21A···O13^iv	0.8600	2.3100	3.142 (3)	163.00
N21—H21B···O11^v	0.8600	2.4200	3.201 (4)	151.00
N22—H22···O28^vi	0.8600	2.3800	3.121 (3)	145.00
N22—H22···O30^vi	0.8600	2.0500	2.755 (3)	138.00
O11—H111···O27^vii	0.84 (3)	2.30 (3)	3.103 (3)	161 (2)
O11—H111···O29^vii	0.84 (3)	2.19 (2)	2.749 (3)	123 (2)
O11—H211···O18^viii	0.835 (13)	1.946 (15)	2.777 (3)	173 (3)
O12—H112···O27	0.84 (2)	1.85 (2)	2.684 (3)	176 (2)
O12—H212···O28ⁱⁱ	0.843 (11)	1.781 (13)	2.619 (2)	172 (3)
O21—H121···O20ⁱⁱⁱ	0.837 (15)	1.846 (14)	2.682 (3)	176 (3)
O21—H221···O17^v	0.84 (2)	1.85 (2)	2.681 (3)	177.0 (17)
O22—H122···O23^ix	0.848 (16)	1.937 (18)	2.780 (2)	173 (3)
O22—H222···O19	0.84 (2)	1.852 (18)	2.646 (3)	157 (3)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z+1; (v) x−1, y, z; (vi) x, y+1, z; (vii) x+1, y, z; (viii) −x+2, −y+1, −z+1; (ix) −x+1, −y, −z+1.

References

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Volume 68| Part 7| July 2012| Pages m900-m901

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