1,4-Diazo-niabicyclo-[2.2.2]octane diaqua-dichlorido-(oxalato-κO,O')iron(III) chloride.

In the title compound, (C(6)H(14)N(2))[Fe(C(2)O(4))Cl(2)(H(2)O)(2)]Cl, all ions are situated on twofold rotational axes. The Fe(III) ion is coordinated by two O atoms from a chelating oxalate ligand, two water mol-ecules and two chloride anions in a distorted octa-hedral geometry. Inter-molecular N-H⋯O, O-H⋯O and O-H⋯Cl hydrogen bonds form an extensive three-dimensional network which consolidates the crystal packing.

Related literature

For the crystal structures of related compounds, see: Fu et al. (2002 ▶); Keene et al. (2004 ▶); Sukhendu & Srinivasan (2007 ▶); Zhao & Xu (2008 ▶); Lee & Wang (1999 ▶).

Experimental

Crystal data

(C6H14N2)[Fe(C2O4)Cl2(H2O)2]Cl

M = 400.44

Monoclinic,

a = 9.872 (2) Å

b = 9.6636 (19) Å

c = 8.4268 (17) Å

β = 109.57 (3)°

V = 757.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.55 mm−1

T = 293 K

0.30 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.638, T max = 0.734

3954 measured reflections

1729 independent reflections

1684 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.049

S = 1.08

1729 reflections

101 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 802 Friedel pairs

Flack parameter: 0.016 (13)

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025628/cv2580sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025628/cv2580Isup2.hkl

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

(C6H14N2)[Fe(C2O4)Cl2(H2O)2]Cl	F(000) = 410
Mr = 400.44	Dx = 1.756 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 3950 reflections
a = 9.872 (2) Å	θ = 3.0–27.5°
b = 9.6636 (19) Å	µ = 1.55 mm−1
c = 8.4268 (17) Å	T = 293 K
β = 109.57 (3)°	Plate, yellow
V = 757.4 (3) Å3	0.30 × 0.30 × 0.20 mm
Z = 2

Rigaku Mercury CCD diffractometer	1729 independent reflections
Radiation source: fine-focus sealed tube	1684 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −12→12
Tmin = 0.638, Tmax = 0.734	k = −12→12
3954 measured reflections	l = −10→10

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.020	w = 1/[σ2(Fo2) + (0.017P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.049	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.17 e Å−3
1729 reflections	Δρmin = −0.15 e Å−3
101 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
1 restraint	Extinction coefficient: 0.0476 (15)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 802 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.016 (13)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
Fe1	0.0000	1.02078 (3)	1.0000	0.02213 (11)
Cl1	0.16532 (6)	1.17560 (5)	1.16036 (7)	0.03727 (16)
Cl2	0.0000	0.85379 (10)	0.5000	0.0462 (2)
N1	0.37619 (17)	0.90236 (18)	0.3965 (2)	0.0285 (4)
H1	0.2853	0.9021	0.3207	0.034*
C1	0.07314 (19)	0.7358 (2)	1.0751 (2)	0.0242 (4)
C2	0.3777 (2)	0.9825 (2)	0.5494 (2)	0.0377 (5)
H2A	0.3047	0.9470	0.5922	0.045*
H2B	0.3572	1.0792	0.5207	0.045*
C3	0.4750 (2)	0.9679 (3)	0.3179 (3)	0.0393 (5)
H3A	0.4386	1.0582	0.2735	0.047*
H3B	0.4812	0.9111	0.2257	0.047*
C4	0.4218 (3)	0.7572 (2)	0.4454 (3)	0.0464 (6)
H4A	0.4088	0.7017	0.3454	0.056*
H4B	0.3638	0.7176	0.5067	0.056*
O1	0.11725 (13)	0.85657 (14)	1.13039 (16)	0.0273 (3)
O2	0.11176 (16)	1.00290 (19)	0.83598 (18)	0.0354 (4)
O3	0.13212 (14)	0.62670 (16)	1.1287 (2)	0.0375 (4)
H2WA	0.199 (3)	1.033 (3)	0.859 (3)	0.046 (7)*
H2WB	0.075 (3)	0.971 (4)	0.741 (4)	0.075 (10)*

	U11	U22	U33	U12	U13	U23
Fe1	0.01824 (19)	0.0248 (2)	0.01995 (18)	0.000	0.00185 (14)	0.000
Cl1	0.0293 (3)	0.0348 (3)	0.0404 (3)	−0.0041 (2)	0.0021 (2)	−0.0136 (2)
Cl2	0.0591 (5)	0.0447 (5)	0.0256 (4)	0.000	0.0019 (3)	0.000
N1	0.0172 (8)	0.0399 (10)	0.0226 (8)	−0.0024 (7)	−0.0010 (7)	0.0007 (7)
C1	0.0175 (9)	0.0296 (10)	0.0273 (9)	0.0010 (7)	0.0099 (8)	0.0025 (7)
C2	0.0249 (10)	0.0499 (15)	0.0397 (11)	0.0031 (9)	0.0125 (9)	−0.0086 (10)
C3	0.0269 (10)	0.0608 (14)	0.0304 (10)	0.0065 (9)	0.0098 (9)	0.0190 (10)
C4	0.0521 (15)	0.0290 (13)	0.0477 (15)	−0.0115 (11)	0.0030 (13)	−0.0061 (11)
O1	0.0207 (7)	0.0276 (7)	0.0262 (7)	0.0018 (6)	−0.0019 (5)	0.0003 (6)
O2	0.0291 (8)	0.0488 (10)	0.0300 (7)	−0.0128 (7)	0.0122 (6)	−0.0117 (8)
O3	0.0294 (7)	0.0313 (8)	0.0520 (10)	0.0096 (6)	0.0139 (7)	0.0145 (7)

Fe1—O2i	2.0443 (14)	C1—C1i	1.569 (4)
Fe1—O2	2.0443 (14)	C2—C3ii	1.515 (3)
Fe1—O1i	2.0526 (14)	C2—H2A	0.9700
Fe1—O1	2.0526 (14)	C2—H2B	0.9700
Fe1—Cl1	2.2913 (8)	C3—C2ii	1.515 (3)
Fe1—Cl1i	2.2913 (8)	C3—H3A	0.9700
N1—C4	1.489 (2)	C3—H3B	0.9700
N1—C3	1.491 (3)	C4—C4ii	1.509 (5)
N1—C2	1.499 (2)	C4—H4A	0.9700
N1—H1	0.9100	C4—H4B	0.9700
C1—O3	1.216 (2)	O2—H2WA	0.87 (3)
C1—O1	1.278 (2)	O2—H2WB	0.82 (3)
O2i—Fe1—O2	170.30 (10)	O1—C1—C1i	113.78 (10)
O2i—Fe1—O1i	87.78 (6)	N1—C2—C3ii	108.47 (16)
O2—Fe1—O1i	84.72 (6)	N1—C2—H2A	110.0
O2i—Fe1—O1	84.72 (6)	C3ii—C2—H2A	110.0
O2—Fe1—O1	87.78 (6)	N1—C2—H2B	110.0
O1i—Fe1—O1	78.73 (8)	C3ii—C2—H2B	110.0
O2i—Fe1—Cl1	95.48 (5)	H2A—C2—H2B	108.4
O2—Fe1—Cl1	90.85 (5)	N1—C3—C2ii	108.72 (15)
O1i—Fe1—Cl1	169.42 (4)	N1—C3—H3A	109.9
O1—Fe1—Cl1	91.53 (5)	C2ii—C3—H3A	109.9
O2i—Fe1—Cl1i	90.85 (5)	N1—C3—H3B	109.9
O2—Fe1—Cl1i	95.48 (5)	C2ii—C3—H3B	109.9
O1i—Fe1—Cl1i	91.53 (5)	H3A—C3—H3B	108.3
O1—Fe1—Cl1i	169.42 (4)	N1—C4—C4ii	108.77 (11)
Cl1—Fe1—Cl1i	98.47 (4)	N1—C4—H4A	109.9
C4—N1—C3	109.93 (18)	C4ii—C4—H4A	109.9
C4—N1—C2	109.49 (17)	N1—C4—H4B	109.9
C3—N1—C2	110.04 (18)	C4ii—C4—H4B	109.9
C4—N1—H1	109.1	H4A—C4—H4B	108.3
C3—N1—H1	109.1	C1—O1—Fe1	116.67 (12)
C2—N1—H1	109.1	Fe1—O2—H2WA	122.9 (15)
O3—C1—O1	126.47 (18)	Fe1—O2—H2WB	122 (2)
O3—C1—C1i	119.75 (12)	H2WA—O2—H2WB	115 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1iii	0.91	1.93	2.814 (2)	162
O2—H2WA···O3iv	0.87 (3)	1.86 (3)	2.722 (2)	168 (2)
O2—H2WB···Cl2	0.82 (3)	2.23 (3)	3.0359 (17)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.91	1.93	2.814 (2)	162
O2—H2WA⋯O3ii	0.87 (3)	1.86 (3)	2.722 (2)	168 (2)
O2—H2WB⋯Cl2	0.82 (3)	2.23 (3)	3.0359 (17)	170 (3)

Symmetry codes: (i) ; (ii) .