Tris(2,2′-bi­pyridine)­iron(II) bis­(1,1,3,3-tetra­cyano-2-eth­oxy­propenide) dihydrate: chiral hydrogen-bonded frameworks inter­penetrate in three dimensions

In the title compound, [Fe(C₁₀H₈N₂)₃](C₉H₅N₄O)₂·2H₂O, the chiral cations lie across twofold rotation axes in the space group C2/c. The anions and the water mol­ecules are linked by two independent O—H...N hydrogen bonds to form C₂²(8) chains, and these chains are linked by the cations via C—H...N and C—H...O hydrogen bonds to form two inter­penetrating three-dimensional frameworks, each of which contains only one enanti­omeric form of the chiral cation.

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Tris(2,2'-bipyridine)iron(II) bis(1,1,3,3-tetracyano-2-ethoxypropenide) dihydrate

Crystal data

[Fe(C10H8N2)3](C9H5N4O)2·2H2O	F(000) = 1928
Mr = 930.77	Dx = 1.366 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9124 reflections
a = 20.273 (4) Å	θ = 3.3–34.8°
b = 12.4463 (6) Å	µ = 0.40 mm^−1
c = 19.4907 (16) Å	T = 150 K
β = 113.080 (9)°	Block, red
V = 4524.3 (9) Å^3	0.16 × 0.10 × 0.05 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	5991 independent reflections
Radiation source: fine-focus sealed tube	4305 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
φ & ω scans	θmax = 29.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −27→24
Tmin = 0.842, Tmax = 0.981	k = −16→16
17754 measured reflections	l = −26→26

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0494P)^2 + 3.4815P] where P = (Fo^2 + 2Fc^2)/3
5991 reflections	(Δ/σ)max = 0.001
304 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

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

	x	y	z	Uiso*/Ueq
Fe1	0.5000	0.63612 (4)	0.7500	0.01652 (13)
N11	0.43186 (10)	0.64656 (16)	0.64498 (11)	0.0198 (4)
C12	0.44707 (12)	0.72318 (19)	0.60388 (13)	0.0209 (5)
C13	0.40172 (14)	0.7440 (2)	0.53006 (14)	0.0279 (6)
H13	0.4140	0.7972	0.5021	0.033*
C14	0.33899 (13)	0.6865 (2)	0.49812 (14)	0.0294 (6)
H14	0.3069	0.7005	0.4482	0.035*
C15	0.32346 (13)	0.6082 (2)	0.53967 (14)	0.0297 (6)
H15	0.2807	0.5672	0.5186	0.036*
C16	0.37092 (13)	0.5900 (2)	0.61239 (14)	0.0260 (6)
H16	0.3600	0.5354	0.6404	0.031*
N21	0.54926 (10)	0.74922 (16)	0.71649 (11)	0.0202 (4)
C22	0.51385 (12)	0.7822 (2)	0.64485 (13)	0.0213 (5)
C23	0.53931 (14)	0.8649 (2)	0.61423 (15)	0.0304 (6)
H23	0.5134	0.8866	0.5641	0.037*
C24	0.60281 (14)	0.9153 (2)	0.65759 (16)	0.0332 (6)
H24	0.6209	0.9726	0.6379	0.040*
C25	0.63942 (14)	0.8809 (2)	0.72990 (16)	0.0326 (6)
H25	0.6837	0.9133	0.7603	0.039*
C26	0.61112 (13)	0.7992 (2)	0.75755 (15)	0.0274 (6)
H26	0.6363	0.7771	0.8078	0.033*
N31	0.55029 (10)	0.51615 (16)	0.72530 (10)	0.0192 (4)
C32	0.52812 (12)	0.4162 (2)	0.73492 (12)	0.0198 (5)
C33	0.55661 (13)	0.3240 (2)	0.71713 (14)	0.0256 (6)
H33	0.5398	0.2552	0.7241	0.031*
C34	0.60933 (14)	0.3325 (2)	0.68938 (15)	0.0306 (6)
H34	0.6288	0.2703	0.6762	0.037*
C35	0.63307 (13)	0.4337 (2)	0.68120 (14)	0.0292 (6)
H35	0.6701	0.4419	0.6633	0.035*
C36	0.60264 (13)	0.5230 (2)	0.69927 (14)	0.0246 (6)
H36	0.6194	0.5921	0.6931	0.030*
C41	0.29850 (14)	0.7499 (2)	0.11874 (14)	0.0279 (6)
C42	0.35522 (13)	0.7675 (2)	0.09577 (14)	0.0277 (6)
C43	0.38757 (14)	0.8649 (2)	0.09320 (14)	0.0306 (6)
C411	0.26362 (14)	0.6494 (2)	0.10597 (15)	0.0319 (6)
N411	0.23421 (14)	0.5681 (2)	0.09626 (15)	0.0423 (6)
C412	0.27632 (14)	0.8256 (2)	0.15939 (16)	0.0336 (7)
N412	0.25669 (15)	0.8829 (2)	0.19377 (16)	0.0490 (7)
O421	0.38154 (10)	0.67546 (15)	0.07861 (11)	0.0320 (4)
C421	0.38097 (15)	0.6646 (2)	0.00419 (15)	0.0328 (7)
H42A	0.3818	0.7364	−0.0173	0.039*
H42B	0.3370	0.6267	−0.0287	0.039*
C422	0.44608 (15)	0.6018 (3)	0.01022 (16)	0.0372 (7)
H42C	0.4463	0.5326	0.0344	0.056*
H42D	0.4893	0.6423	0.0400	0.056*
H42E	0.4452	0.5893	−0.0398	0.056*
C431	0.45341 (16)	0.8685 (2)	0.08320 (15)	0.0325 (6)
N431	0.50640 (14)	0.8706 (2)	0.07531 (14)	0.0407 (6)
C432	0.35529 (15)	0.9663 (2)	0.09688 (15)	0.0336 (7)
N432	0.32946 (14)	1.0475 (2)	0.09803 (14)	0.0444 (7)
O1W	0.27576 (16)	0.8453 (2)	0.34988 (16)	0.0719 (8)
H1A	0.2652	0.8601	0.2946	0.108*
H1B	0.2792	0.9216	0.3686	0.108*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0155 (2)	0.0166 (2)	0.0175 (2)	0.000	0.00660 (17)	0.000
N11	0.0195 (10)	0.0186 (11)	0.0227 (9)	0.0007 (8)	0.0098 (8)	−0.0005 (8)
C12	0.0232 (12)	0.0187 (13)	0.0224 (11)	0.0009 (9)	0.0106 (9)	−0.0008 (10)
C13	0.0317 (14)	0.0304 (15)	0.0233 (12)	0.0002 (11)	0.0125 (10)	0.0044 (11)
C14	0.0263 (13)	0.0384 (16)	0.0188 (12)	0.0045 (11)	0.0039 (10)	0.0011 (11)
C15	0.0212 (13)	0.0354 (16)	0.0273 (13)	−0.0058 (10)	0.0037 (10)	−0.0023 (11)
C16	0.0220 (12)	0.0292 (14)	0.0242 (12)	−0.0048 (10)	0.0063 (10)	0.0006 (11)
N21	0.0191 (10)	0.0204 (11)	0.0237 (10)	−0.0035 (8)	0.0111 (8)	−0.0029 (8)
C22	0.0218 (12)	0.0222 (13)	0.0235 (12)	0.0000 (9)	0.0129 (10)	−0.0019 (10)
C23	0.0327 (14)	0.0308 (15)	0.0309 (13)	−0.0023 (12)	0.0158 (11)	0.0046 (12)
C24	0.0359 (15)	0.0270 (16)	0.0456 (17)	−0.0067 (12)	0.0256 (13)	0.0027 (13)
C25	0.0296 (14)	0.0319 (17)	0.0390 (15)	−0.0118 (11)	0.0166 (12)	−0.0091 (13)
C26	0.0236 (13)	0.0308 (15)	0.0283 (13)	−0.0046 (10)	0.0108 (10)	−0.0034 (11)
N31	0.0165 (9)	0.0233 (11)	0.0164 (9)	−0.0001 (8)	0.0049 (7)	−0.0015 (8)
C32	0.0192 (11)	0.0206 (13)	0.0153 (10)	0.0011 (9)	0.0020 (9)	0.0006 (9)
C33	0.0274 (13)	0.0224 (13)	0.0240 (12)	0.0022 (10)	0.0069 (10)	−0.0022 (10)
C34	0.0323 (14)	0.0284 (15)	0.0283 (13)	0.0112 (11)	0.0089 (11)	−0.0065 (11)
C35	0.0221 (13)	0.0385 (16)	0.0289 (13)	0.0050 (11)	0.0120 (10)	−0.0062 (12)
C36	0.0208 (12)	0.0286 (15)	0.0252 (12)	−0.0012 (10)	0.0097 (10)	−0.0029 (11)
C41	0.0266 (13)	0.0309 (15)	0.0255 (13)	0.0098 (11)	0.0094 (10)	−0.0001 (11)
C42	0.0280 (14)	0.0316 (16)	0.0212 (12)	0.0136 (11)	0.0073 (10)	0.0041 (11)
C43	0.0367 (15)	0.0294 (15)	0.0243 (12)	0.0098 (12)	0.0103 (11)	0.0033 (12)
C411	0.0309 (14)	0.0361 (18)	0.0337 (14)	0.0121 (12)	0.0181 (11)	0.0016 (13)
N411	0.0415 (15)	0.0421 (17)	0.0533 (16)	0.0046 (12)	0.0293 (12)	−0.0022 (13)
C412	0.0285 (14)	0.0407 (17)	0.0313 (14)	0.0078 (12)	0.0115 (11)	−0.0004 (13)
N412	0.0537 (17)	0.0511 (19)	0.0526 (17)	0.0065 (13)	0.0320 (14)	−0.0113 (14)
O421	0.0390 (11)	0.0284 (10)	0.0362 (10)	0.0148 (8)	0.0229 (9)	0.0049 (9)
C421	0.0348 (15)	0.0347 (17)	0.0249 (13)	0.0064 (11)	0.0073 (11)	−0.0050 (12)
C422	0.0374 (16)	0.0439 (19)	0.0344 (15)	0.0101 (13)	0.0185 (12)	−0.0034 (13)
C431	0.0419 (16)	0.0264 (15)	0.0259 (13)	0.0037 (12)	0.0097 (11)	0.0032 (12)
N431	0.0456 (15)	0.0380 (15)	0.0426 (14)	−0.0037 (12)	0.0218 (12)	−0.0023 (12)
C432	0.0392 (16)	0.0348 (17)	0.0223 (13)	0.0068 (13)	0.0074 (11)	0.0021 (12)
N432	0.0554 (16)	0.0350 (16)	0.0346 (13)	0.0173 (12)	0.0090 (12)	−0.0008 (12)
O1W	0.095 (2)	0.0594 (19)	0.0708 (18)	0.0148 (15)	0.0428 (16)	0.0088 (14)

Geometric parameters (Å, º)

Fe1—N11	1.9744 (19)	C32—C32^i	1.473 (5)
Fe1—N11^i	1.9744 (19)	C32—C33	1.389 (3)
Fe1—N21^i	1.979 (2)	C33—H33	0.9500
Fe1—N21	1.979 (2)	C33—C34	1.378 (4)
Fe1—N31	1.971 (2)	C34—H34	0.9500
Fe1—N31^i	1.971 (2)	C34—C35	1.379 (4)
N11—C12	1.356 (3)	C35—H35	0.9500
N11—C16	1.345 (3)	C35—C36	1.382 (4)
C12—C13	1.395 (3)	C36—H36	0.9500
C12—C22	1.470 (3)	C41—C42	1.405 (4)
C13—H13	0.9500	C41—C411	1.411 (4)
C13—C14	1.377 (4)	C41—C412	1.413 (4)
C14—H14	0.9500	C42—C43	1.388 (4)
C14—C15	1.380 (4)	C42—O421	1.360 (3)
C15—H15	0.9500	C43—C431	1.423 (4)
C15—C16	1.384 (3)	C43—C432	1.436 (4)
C16—H16	0.9500	C411—N411	1.151 (4)
N21—C22	1.359 (3)	C412—N412	1.151 (4)
N21—C26	1.347 (3)	O421—C421	1.452 (3)
C22—C23	1.387 (4)	C421—H42A	0.9900
C23—H23	0.9500	C421—H42B	0.9900
C23—C24	1.383 (4)	C421—C422	1.499 (4)
C24—H24	0.9500	C422—H42C	0.9800
C24—C25	1.378 (4)	C422—H42D	0.9800
C25—H25	0.9500	C422—H42E	0.9800
C25—C26	1.377 (4)	C431—N431	1.144 (4)
C26—H26	0.9500	C432—N432	1.142 (4)
N31—C32	1.360 (3)	O1W—H1A	1.0292
N31—C36	1.347 (3)	O1W—H1B	1.0099
N11—Fe1—N11^i	172.46 (12)	N21—C26—C25	122.8 (2)
N11^i—Fe1—N21	93.27 (8)	N21—C26—H26	118.6
N11—Fe1—N21^i	93.26 (8)	C25—C26—H26	118.6
N11^i—Fe1—N21^i	81.35 (8)	C32—N31—Fe1	115.38 (16)
N11—Fe1—N21	81.35 (8)	C36—N31—Fe1	127.14 (17)
N21—Fe1—N21^i	89.33 (12)	C36—N31—C32	117.5 (2)
N31—Fe1—N11	90.87 (8)	N31—C32—C32^i	113.83 (14)
N31^i—Fe1—N11^i	90.87 (8)	N31—C32—C33	122.0 (2)
N31^i—Fe1—N11	94.84 (8)	C33—C32—C32^i	124.21 (16)
N31—Fe1—N11^i	94.84 (8)	C32—C33—H33	120.1
N31—Fe1—N21	94.70 (8)	C34—C33—C32	119.8 (3)
N31—Fe1—N21^i	174.62 (8)	C34—C33—H33	120.1
N31^i—Fe1—N21	174.62 (8)	C33—C34—H34	120.8
N31^i—Fe1—N21^i	94.70 (8)	C33—C34—C35	118.4 (2)
N31—Fe1—N31^i	81.50 (12)	C35—C34—H34	120.8
C12—N11—Fe1	115.46 (15)	C34—C35—H35	120.2
C16—N11—Fe1	126.50 (17)	C34—C35—C36	119.6 (3)
C16—N11—C12	117.9 (2)	C36—C35—H35	120.2
N11—C12—C13	122.0 (2)	N31—C36—C35	122.8 (3)
N11—C12—C22	113.9 (2)	N31—C36—H36	118.6
C13—C12—C22	124.2 (2)	C35—C36—H36	118.6
C12—C13—H13	120.4	C42—C41—C411	119.9 (2)
C14—C13—C12	119.2 (2)	C42—C41—C412	123.7 (3)
C14—C13—H13	120.4	C411—C41—C412	116.3 (3)
C13—C14—H14	120.5	C43—C42—C41	127.2 (2)
C13—C14—C15	119.0 (2)	O421—C42—C41	113.3 (2)
C15—C14—H14	120.5	O421—C42—C43	119.4 (2)
C14—C15—H15	120.4	C42—C43—C431	121.0 (3)
C14—C15—C16	119.3 (2)	C42—C43—C432	122.3 (3)
C16—C15—H15	120.4	C431—C43—C432	116.7 (3)
N11—C16—C15	122.6 (2)	N411—C411—C41	178.5 (3)
N11—C16—H16	118.7	N412—C412—C41	176.4 (4)
C15—C16—H16	118.7	C42—O421—C421	118.3 (2)
C22—N21—Fe1	114.96 (15)	O421—C421—H42A	110.1
C26—N21—Fe1	127.25 (17)	O421—C421—H42B	110.1
C26—N21—C22	117.7 (2)	O421—C421—C422	108.0 (2)
N21—C22—C12	114.2 (2)	H42A—C421—H42B	108.4
N21—C22—C23	122.0 (2)	C422—C421—H42A	110.1
C23—C22—C12	123.8 (2)	C422—C421—H42B	110.1
C22—C23—H23	120.4	C421—C422—H42C	109.5
C24—C23—C22	119.2 (2)	C421—C422—H42D	109.5
C24—C23—H23	120.4	C421—C422—H42E	109.5
C23—C24—H24	120.5	H42C—C422—H42D	109.5
C25—C24—C23	118.9 (3)	H42C—C422—H42E	109.5
C25—C24—H24	120.5	H42D—C422—H42E	109.5
C24—C25—H25	120.4	N431—C431—C43	179.5 (3)
C26—C25—C24	119.3 (2)	N432—C432—C43	178.3 (3)
C26—C25—H25	120.4	H1A—O1W—H1B	99.5
Fe1—N11—C12—C13	−176.4 (2)	N21—Fe1—N31—C36	3.60 (19)
Fe1—N11—C12—C22	2.3 (3)	N21—C22—C23—C24	0.3 (4)
Fe1—N11—C16—C15	175.1 (2)	C22—C12—C13—C14	−177.4 (2)
Fe1—N21—C22—C12	−3.3 (3)	C22—N21—C26—C25	−0.2 (4)
Fe1—N21—C22—C23	176.4 (2)	C22—C23—C24—C25	0.7 (4)
Fe1—N21—C26—C25	−176.8 (2)	C23—C24—C25—C26	−1.4 (4)
Fe1—N31—C32—C32^i	−2.2 (3)	C24—C25—C26—N21	1.2 (4)
Fe1—N31—C32—C33	177.50 (17)	C26—N21—C22—C12	179.7 (2)
Fe1—N31—C36—C35	−177.79 (18)	C26—N21—C22—C23	−0.6 (4)
N11—Fe1—N21—C22	3.54 (17)	N31—Fe1—N11—C12	−97.82 (18)
N11^i—Fe1—N21—C22	−171.15 (17)	N31^i—Fe1—N11—C12	−179.37 (17)
N11—Fe1—N21—C26	−179.8 (2)	N31^i—Fe1—N11—C16	4.6 (2)
N11^i—Fe1—N21—C26	5.5 (2)	N31—Fe1—N11—C16	86.2 (2)
N11^i—Fe1—N31—C32	91.00 (16)	N31—Fe1—N21—C22	93.71 (17)
N11—Fe1—N31—C32	−93.92 (16)	N31—Fe1—N21—C26	−89.7 (2)
N11—Fe1—N31—C36	84.99 (19)	N31^i—Fe1—N31—C32	0.84 (11)
N11^i—Fe1—N31—C36	−90.1 (2)	N31^i—Fe1—N31—C36	179.8 (2)
N11—C12—C13—C14	1.1 (4)	N31—C32—C33—C34	0.5 (3)
N11—C12—C22—N21	0.6 (3)	C32—N31—C36—C35	1.1 (3)
N11—C12—C22—C23	−179.1 (2)	C32^i—C32—C33—C34	−179.8 (3)
C12—N11—C16—C15	−0.9 (4)	C32—C33—C34—C35	1.0 (4)
C12—C13—C14—C15	−1.3 (4)	C33—C34—C35—C36	−1.4 (4)
C12—C22—C23—C24	180.0 (2)	C34—C35—C36—N31	0.4 (4)
C13—C12—C22—N21	179.3 (2)	C36—N31—C32—C32^i	178.7 (2)
C13—C12—C22—C23	−0.4 (4)	C36—N31—C32—C33	−1.5 (3)
C13—C14—C15—C16	0.5 (4)	C41—C42—C43—C431	167.2 (2)
C14—C15—C16—N11	0.6 (4)	C41—C42—C43—C432	−15.7 (4)
C16—N11—C12—C13	0.0 (4)	C41—C42—O421—C421	122.0 (2)
C16—N11—C12—C22	178.7 (2)	C42—O421—C421—C422	145.8 (2)
N21^i—Fe1—N11—C12	85.63 (18)	C43—C42—C41—C411	169.1 (2)
N21—Fe1—N11—C12	−3.20 (17)	C43—C42—C41—C412	−15.5 (4)
N21—Fe1—N11—C16	−179.2 (2)	C43—C42—O421—C421	−61.3 (3)
N21^i—Fe1—N11—C16	−90.4 (2)	C411—C41—C42—O421	−14.6 (3)
N21^i—Fe1—N21—C22	−89.86 (17)	C412—C41—C42—O421	160.8 (2)
N21^i—Fe1—N21—C26	86.8 (2)	O421—C42—C43—C431	−8.9 (4)
N21—Fe1—N31—C32	−175.31 (16)	O421—C42—C43—C432	168.2 (2)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

Cg1 represents the centroid of the N11/C12–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1W	0.95	2.52	3.316 (4)	141
C15—H15···N432^ii	0.95	2.50	3.296 (4)	142
C23—H23···N431^iii	0.95	2.59	3.439 (4)	148
C26—H26···Cg1^i	0.95	2.91	3.697 (3)	141
O1W—H1A···N412	1.03	1.93	2.950 (4)	173
O1W—H1B···N411^iv	1.01	2.00	3.000 (4)	169

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1, y, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2.