1:1 Co-crystal of 4,4′-(ethene-1,2-di­yl)dipyridin-1-ium sulfate and hexa­aqua­iron(II) sulfate monohydrate

Yang, D.; Yang, F.-L.

doi:10.1107/S1600536814007053

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page m169

doi:10.1107/S1600536814007053

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1:1 Co-crystal of 4,4′-(ethene-1,2-diyl)dipyridin-1-ium sulfate and hexaaquairon(II) sulfate monohydrate

Dan Yang ^a ^* and Fei-Lin Yang ^a

^aSchool of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, People's Republic of China
^*Correspondence e-mail: aihua.yuan@just.edu.cn

(Received 27 March 2014; accepted 30 March 2014; online 5 April 2014)

In the title hydrated double salt, 4,4′-(ethene-1,2-diyl)dipyridin-1-ium hexaaquairon(II) bis(sulfate) monohydrate, (C₁₂H₁₂N₂)[Fe(H₂O)₆](SO₄)₂·H₂O, the Fe^II cation is coordinated by six water molecules in a slightly distorted octahedral geometry; the two pyridine rings of the 4,4′-(ethene-1,2-diyl)dipyridin-1-ium cation are twisted to each other by a dihedral angle of 11.84 (10)°. In the crystal, the cations, sulfate anions and water molecules of crystallization are linked by O—H⋯O, N—H⋯O and weak C—H⋯O hydrogen bonds, forming a three-dimensional supramolecular network.

CCDC reference: 994508

Related literature

For a related structure, see: Prakash et al. (2012 ). For the synthesis, see: Bok et al. (1975 ).

Experimental

Crystal data

(C₁₂H₁₂N₂)[Fe(H₂O)₆](SO₄)₂·H₂O
M_r = 558.32
Triclinic, $[P \overline 1]$
a = 6.772 (1) Å
b = 12.5006 (18) Å
c = 14.187 (2) Å
α = 68.991 (2)°
β = 81.829 (2)°
γ = 87.925 (2)°
V = 1109.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 173 K
0.26 × 0.23 × 0.08 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.79, T_max = 0.93
8479 measured reflections
4117 independent reflections
3601 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.072
S = 1.04
4117 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1X⋯O13	0.89	1.74	2.622 (2)	173
N2—H2X⋯O10ⁱ	0.89	1.75	2.631 (2)	170
O1—H1WB⋯O7	0.85	1.89	2.733 (2)	175
O1—H1WA⋯O9ⁱⁱ	0.85	1.90	2.741 (2)	170
O2—H2WA⋯O8	0.85	1.90	2.719 (2)	161
O2—H2WB⋯O12	0.85	1.86	2.711 (2)	175
O3—H3WA⋯O8ⁱⁱ	0.85	1.91	2.751 (2)	169
O3—H3WB⋯O11	0.85	1.88	2.726 (2)	174
O4—H4WA⋯O11ⁱⁱⁱ	0.85	1.85	2.696 (2)	171
O4—H4WB⋯O12^iv	0.85	1.86	2.710 (2)	175
O5—H5WA⋯O15	0.85	1.90	2.742 (2)	169
O5—H5WB⋯O14ⁱⁱⁱ	0.85	1.90	2.750 (2)	175
O6—H6WA⋯O15^v	0.85	1.93	2.763 (2)	165
O6—H6WB⋯O14^iv	0.85	1.89	2.739 (2)	180
O15—H15A⋯O9ⁱⁱ	0.85	1.97	2.780 (2)	159
O15—H15B⋯O7^vi	0.85	1.92	2.7628 (19)	174
C1—H1⋯O8^vii	0.95	2.48	3.339 (3)	150
C1—H1⋯O10^vii	0.95	2.31	3.172 (2)	150
C11—H11⋯O13^viii	0.95	2.34	3.189 (2)	149
C11—H11⋯O14^viii	0.95	2.43	3.291 (3)	151
Symmetry codes: (i) -x, -y, -z; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1; (iv) -x, -y+1, -z+1; (v) x-1, y, z; (vi) -x+1, -y+1, -z; (vii) -x, -y, -z+1; (viii) x, y, z-1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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, 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 994508

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814007053/xu5782sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814007053/xu5782Isup2.hkl

checkCIF report

Comment top

In this paper, we used [Mo(CN)₈]^3- as building block to react with transition metal Fe²⁺ ions and 1,2-di(pyridin-4-yl)ethylene ligand (dpe), in order to obtain octacyanometalate-based bimetallic compound. Unfortunately, the title ion-type compound was obtained. The asymmetric unit of the title compound contains one 1,2-bis-(4-pyridyl)ethylene cation, [H₂dpe]²⁺, two sulfate anions, one hexaaqua-iron(II) cation, and one crystallized water molecule (Fig. 1). In the structure, the Fe atom adopts a distorted slightly octahedral geometry, in which the average distance of Fe—O bonds is about 2.118 Å. The [Fe(H₂O)₆]²⁺ cations, sulfate anions, and guest water molecules are linked by O—H···O hydrogen bonds, forming a two-dimensional (2-D) layered structure. The N—H···O hydrogen bonds between adjacent layers generate a 3-D supramolecular network (Fig. 2). The structure of the title compound is comparable to that observed in related compound (Prakash et al., 2012).

Related literature top

For a related structure, see: Prakash et al. (2012). For the synthesis, see: Bok et al. (1975).

Experimental top

The title compound was prepared at room temperature by slow diffusion between a CH₃CH₂OH/H₂O (V/V = 2:1) solution containing FeSO₄.7H₂O (0.05 mmol) and dpe ligand (0.10 mmol), and a CH₃CH₂OH/H₂O (V:V = 2:1) solution of [HN(n-C₄H₉)₃]₃[Mo(CN)₈].4H₂O (0.025 mmol) (Bok et al., 1975). After two weeks, brown plate crystals were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with thermal ellipsoids at the 30% probability level. All H atoms were omitted for clarity.
	Fig. 2. The three-dimensional supramolecular network of the title compound.

4,4'-(Ethene-1,2-diyl)dipyridin-1-ium hexaaquairon(II) bis(sulfate) monohydrate top

Crystal data top

(C₁₂H₁₂N₂)[Fe(H₂O)₆](SO₄)₂·H₂O	Z = 2
M_r = 558.32	F(000) = 580
Triclinic, P1	D_x = 1.671 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.772 (1) Å	Cell parameters from 4117 reflections
b = 12.5006 (18) Å	θ = 3.0–25.6°
c = 14.187 (2) Å	µ = 0.94 mm⁻¹
α = 68.991 (2)°	T = 173 K
β = 81.829 (2)°	Plate, brown
γ = 87.925 (2)°	0.26 × 0.23 × 0.08 mm
V = 1109.6 (3) Å³

Data collection top

Bruker SMART APEXII diffractometer	4117 independent reflections
Radiation source: fine-focus sealed tube	3601 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
phi and ω scans	θ_max = 25.6°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
T_min = 0.79, T_max = 0.93	k = −15→15
8479 measured reflections	l = −17→17

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0384P)² + 0.3901P] where P = (F_o² + 2F_c²)/3
4117 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

(C₁₂H₁₂N₂)[Fe(H₂O)₆](SO₄)₂·H₂O	γ = 87.925 (2)°
M_r = 558.32	V = 1109.6 (3) Å³
Triclinic, P1	Z = 2
a = 6.772 (1) Å	Mo Kα radiation
b = 12.5006 (18) Å	µ = 0.94 mm⁻¹
c = 14.187 (2) Å	T = 173 K
α = 68.991 (2)°	0.26 × 0.23 × 0.08 mm
β = 81.829 (2)°

Data collection top

Bruker SMART APEXII diffractometer	4117 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3601 reflections with I > 2σ(I)
T_min = 0.79, T_max = 0.93	R_int = 0.014
8479 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.04	Δρ_max = 0.30 e Å⁻³
4117 reflections	Δρ_min = −0.42 e Å⁻³
289 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Fe1	0.30537 (4)	0.51818 (2)	0.268630 (19)	0.02402 (9)
S1	−0.15024 (7)	0.27787 (4)	0.19605 (3)	0.02389 (11)
S2	0.25179 (7)	0.26222 (4)	0.62987 (3)	0.02462 (11)
N1	0.2643 (2)	0.05496 (15)	0.51392 (12)	0.0323 (4)
H1X	0.2705	0.0772	0.5664	0.039*
N2	0.2490 (2)	−0.07642 (15)	−0.08553 (12)	0.0319 (4)
H2X	0.2430	−0.0967	−0.1392	0.038*
O1	0.3515 (2)	0.42427 (13)	0.17016 (12)	0.0423 (4)
H1WA	0.4625	0.4022	0.1478	0.063*
H1WB	0.2660	0.3818	0.1614	0.063*
O2	0.0864 (2)	0.40216 (14)	0.36832 (11)	0.0489 (4)
H2WA	0.0035	0.3615	0.3555	0.073*
H2WB	0.0820	0.3740	0.4327	0.073*
O3	0.5165 (2)	0.42177 (14)	0.35920 (11)	0.0455 (4)
H3WA	0.6108	0.3812	0.3446	0.068*
H3WB	0.4920	0.3939	0.4239	0.068*
O4	0.2662 (2)	0.63014 (14)	0.35026 (12)	0.0444 (4)
H4WA	0.3541	0.6413	0.3831	0.067*
H4WB	0.1579	0.6494	0.3778	0.067*
O5	0.53157 (19)	0.63820 (11)	0.17344 (10)	0.0319 (3)
H5WA	0.6162	0.6194	0.1321	0.048*
H5WB	0.6023	0.6616	0.2073	0.048*
O6	0.0777 (2)	0.61071 (12)	0.18625 (10)	0.0333 (3)
H6WA	0.0236	0.5954	0.1419	0.050*
H6WB	−0.0144	0.6420	0.2141	0.050*
O7	0.0587 (2)	0.29477 (12)	0.14664 (10)	0.0339 (3)
O8	−0.1730 (2)	0.31232 (12)	0.28575 (10)	0.0355 (3)
O9	−0.2785 (2)	0.34627 (13)	0.12172 (11)	0.0378 (3)
O10	−0.2059 (2)	0.15596 (11)	0.22994 (10)	0.0388 (4)
O11	0.4357 (2)	0.31751 (15)	0.56561 (11)	0.0457 (4)
O12	0.0825 (2)	0.29986 (14)	0.57251 (10)	0.0400 (4)
O13	0.2703 (3)	0.13740 (12)	0.65942 (11)	0.0481 (4)
O14	0.2198 (2)	0.28888 (12)	0.72368 (10)	0.0325 (3)
O15	0.8392 (2)	0.57495 (12)	0.05726 (10)	0.0363 (3)
H15A	0.8100	0.5079	0.0608	0.054*
H15B	0.8754	0.6109	−0.0059	0.054*
C1	0.2380 (3)	−0.05528 (18)	0.52884 (14)	0.0326 (4)
H1	0.2182	−0.1102	0.5962	0.039*
C2	0.2395 (3)	−0.08957 (17)	0.44725 (14)	0.0312 (4)
H2	0.2230	−0.1684	0.4581	0.037*
C3	0.2651 (3)	−0.00942 (16)	0.34859 (13)	0.0255 (4)
C4	0.2926 (3)	0.10517 (17)	0.33679 (15)	0.0340 (5)
H4	0.3117	0.1624	0.2705	0.041*
C5	0.2919 (3)	0.13460 (18)	0.42025 (16)	0.0364 (5)
H5	0.3112	0.2125	0.4119	0.044*
C6	0.2634 (3)	−0.04685 (16)	0.26238 (14)	0.0303 (4)
H6	0.2730	−0.1267	0.2750	0.036*
C7	0.2494 (3)	0.02256 (16)	0.16764 (14)	0.0273 (4)
H7	0.2379	0.1022	0.1554	0.033*
C8	0.2502 (3)	−0.01417 (15)	0.08059 (13)	0.0249 (4)
C9	0.2601 (3)	−0.12954 (16)	0.08962 (14)	0.0297 (4)
H9	0.2673	−0.1878	0.1542	0.036*
C10	0.2595 (3)	−0.15785 (17)	0.00524 (15)	0.0326 (4)
H10	0.2666	−0.2360	0.0112	0.039*
C11	0.2405 (3)	0.03440 (17)	−0.09822 (14)	0.0321 (4)
H11	0.2340	0.0902	−0.1640	0.038*
C12	0.2412 (3)	0.06773 (16)	−0.01616 (14)	0.0290 (4)
H12	0.2356	0.1468	−0.0252	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.02364 (15)	0.02605 (15)	0.02441 (15)	0.00119 (11)	−0.00470 (11)	−0.01102 (11)
S1	0.0272 (2)	0.0257 (2)	0.0205 (2)	−0.00155 (18)	−0.00298 (18)	−0.01036 (18)
S2	0.0258 (2)	0.0328 (2)	0.0187 (2)	0.00145 (19)	−0.00384 (17)	−0.01322 (19)
N1	0.0343 (9)	0.0449 (10)	0.0267 (9)	0.0050 (8)	−0.0070 (7)	−0.0228 (8)
N2	0.0331 (9)	0.0448 (10)	0.0233 (8)	−0.0038 (8)	−0.0019 (7)	−0.0191 (7)
O1	0.0308 (8)	0.0552 (9)	0.0579 (10)	0.0007 (7)	−0.0048 (7)	−0.0413 (8)
O2	0.0513 (10)	0.0627 (10)	0.0264 (8)	−0.0277 (8)	−0.0064 (7)	−0.0051 (7)
O3	0.0424 (9)	0.0622 (10)	0.0300 (8)	0.0226 (8)	−0.0101 (7)	−0.0144 (7)
O4	0.0270 (8)	0.0698 (11)	0.0579 (10)	0.0054 (7)	−0.0072 (7)	−0.0486 (9)
O5	0.0273 (7)	0.0379 (8)	0.0338 (7)	−0.0032 (6)	−0.0007 (6)	−0.0177 (6)
O6	0.0294 (7)	0.0426 (8)	0.0345 (8)	0.0093 (6)	−0.0119 (6)	−0.0198 (6)
O7	0.0279 (7)	0.0415 (8)	0.0301 (7)	0.0005 (6)	−0.0014 (6)	−0.0111 (6)
O8	0.0384 (8)	0.0436 (8)	0.0344 (8)	0.0005 (6)	−0.0042 (6)	−0.0263 (7)
O9	0.0337 (8)	0.0450 (9)	0.0342 (8)	0.0066 (6)	−0.0112 (6)	−0.0118 (7)
O10	0.0636 (10)	0.0299 (7)	0.0232 (7)	−0.0138 (7)	−0.0015 (7)	−0.0104 (6)
O11	0.0299 (8)	0.0764 (12)	0.0274 (8)	−0.0122 (8)	0.0002 (6)	−0.0150 (8)
O12	0.0278 (8)	0.0661 (10)	0.0281 (7)	0.0064 (7)	−0.0081 (6)	−0.0181 (7)
O13	0.0878 (13)	0.0342 (8)	0.0298 (8)	0.0099 (8)	−0.0152 (8)	−0.0185 (7)
O14	0.0366 (8)	0.0414 (8)	0.0274 (7)	0.0038 (6)	−0.0050 (6)	−0.0218 (6)
O15	0.0439 (9)	0.0407 (8)	0.0249 (7)	−0.0010 (7)	−0.0013 (6)	−0.0137 (6)
C1	0.0354 (11)	0.0403 (11)	0.0201 (9)	−0.0005 (9)	−0.0024 (8)	−0.0088 (8)
C2	0.0416 (12)	0.0284 (10)	0.0250 (10)	0.0002 (9)	−0.0062 (8)	−0.0105 (8)
C3	0.0270 (10)	0.0288 (10)	0.0227 (9)	0.0022 (8)	−0.0042 (7)	−0.0114 (8)
C4	0.0509 (13)	0.0268 (10)	0.0251 (10)	−0.0001 (9)	−0.0075 (9)	−0.0093 (8)
C5	0.0487 (13)	0.0309 (11)	0.0361 (11)	0.0030 (9)	−0.0109 (10)	−0.0182 (9)
C6	0.0434 (12)	0.0269 (10)	0.0242 (10)	0.0004 (8)	−0.0047 (8)	−0.0134 (8)
C7	0.0336 (11)	0.0266 (9)	0.0260 (10)	0.0036 (8)	−0.0072 (8)	−0.0139 (8)
C8	0.0255 (10)	0.0285 (9)	0.0218 (9)	0.0008 (8)	−0.0043 (7)	−0.0101 (8)
C9	0.0413 (12)	0.0267 (10)	0.0223 (9)	0.0018 (8)	−0.0075 (8)	−0.0091 (8)
C10	0.0404 (12)	0.0314 (10)	0.0302 (10)	−0.0005 (9)	−0.0045 (9)	−0.0163 (9)
C11	0.0355 (11)	0.0372 (11)	0.0195 (9)	−0.0052 (9)	−0.0039 (8)	−0.0046 (8)
C12	0.0337 (11)	0.0281 (10)	0.0246 (9)	−0.0025 (8)	−0.0054 (8)	−0.0079 (8)

Geometric parameters (Å, º) top

Fe1—O2	2.0954 (14)	O5—H5WA	0.8500
Fe1—O4	2.1019 (14)	O5—H5WB	0.8500
Fe1—O3	2.1059 (14)	O6—H6WA	0.8502
Fe1—O1	2.1101 (14)	O6—H6WB	0.8498
Fe1—O6	2.1199 (13)	O15—H15A	0.8499
Fe1—O5	2.1323 (13)	O15—H15B	0.8498
S1—O9	1.4690 (14)	C1—C2	1.370 (3)
S1—O10	1.4698 (14)	C1—H1	0.9500
S1—O8	1.4700 (13)	C2—C3	1.390 (3)
S1—O7	1.4738 (14)	C2—H2	0.9500
S2—O11	1.4656 (15)	C3—C4	1.397 (3)
S2—O12	1.4663 (14)	C3—C6	1.459 (2)
S2—O13	1.4690 (15)	C4—C5	1.359 (3)
S2—O14	1.4696 (13)	C4—H4	0.9500
N1—C1	1.332 (3)	C5—H5	0.9500
N1—C5	1.336 (3)	C6—C7	1.328 (3)
N1—H1X	0.8902	C6—H6	0.9500
N2—C11	1.332 (3)	C7—C8	1.463 (2)
N2—C10	1.334 (3)	C7—H7	0.9500
N2—H2X	0.8901	C8—C12	1.396 (3)
O1—H1WA	0.8500	C8—C9	1.401 (3)
O1—H1WB	0.8500	C9—C10	1.365 (2)
O2—H2WA	0.8499	C9—H9	0.9500
O2—H2WB	0.8499	C10—H10	0.9500
O3—H3WA	0.8499	C11—C12	1.371 (3)
O3—H3WB	0.8506	C11—H11	0.9500
O4—H4WA	0.8500	C12—H12	0.9500
O4—H4WB	0.8500

O2—Fe1—O4	93.26 (6)	H4WA—O4—H4WB	104.0
O2—Fe1—O3	87.76 (6)	Fe1—O5—H5WA	119.6
O4—Fe1—O3	92.10 (6)	Fe1—O5—H5WB	112.5
O2—Fe1—O1	92.61 (6)	H5WA—O5—H5WB	104.2
O4—Fe1—O1	172.85 (6)	Fe1—O6—H6WA	127.3
O3—Fe1—O1	92.22 (6)	Fe1—O6—H6WB	120.8
O2—Fe1—O6	88.65 (6)	H6WA—O6—H6WB	104.1
O4—Fe1—O6	86.54 (6)	H15A—O15—H15B	104.2
O3—Fe1—O6	176.09 (5)	N1—C1—C2	120.11 (18)
O1—Fe1—O6	89.51 (6)	N1—C1—H1	119.9
O2—Fe1—O5	177.16 (5)	C2—C1—H1	119.9
O4—Fe1—O5	84.35 (6)	C1—C2—C3	120.25 (18)
O3—Fe1—O5	90.80 (6)	C1—C2—H2	119.9
O1—Fe1—O5	89.89 (6)	C3—C2—H2	119.9
O6—Fe1—O5	92.72 (5)	C2—C3—C4	117.53 (16)
O9—S1—O10	109.65 (9)	C2—C3—C6	119.71 (16)
O9—S1—O8	110.74 (9)	C4—C3—C6	122.76 (17)
O10—S1—O8	108.44 (8)	C5—C4—C3	119.92 (18)
O9—S1—O7	108.66 (8)	C5—C4—H4	120.0
O10—S1—O7	109.39 (9)	C3—C4—H4	120.0
O8—S1—O7	109.95 (8)	N1—C5—C4	120.65 (18)
O11—S2—O12	109.56 (9)	N1—C5—H5	119.7
O11—S2—O13	108.96 (10)	C4—C5—H5	119.7
O12—S2—O13	109.22 (9)	C7—C6—C3	124.73 (17)
O11—S2—O14	110.64 (8)	C7—C6—H6	117.6
O12—S2—O14	110.64 (8)	C3—C6—H6	117.6
O13—S2—O14	107.78 (8)	C6—C7—C8	125.04 (17)
C1—N1—C5	121.54 (16)	C6—C7—H7	117.5
C1—N1—H1X	120.5	C8—C7—H7	117.5
C5—N1—H1X	117.9	C12—C8—C9	117.67 (16)
C11—N2—C10	122.22 (16)	C12—C8—C7	119.59 (16)
C11—N2—H2X	118.6	C9—C8—C7	122.74 (16)
C10—N2—H2X	119.1	C10—C9—C8	119.68 (18)
Fe1—O1—H1WA	126.9	C10—C9—H9	120.2
Fe1—O1—H1WB	126.3	C8—C9—H9	120.2
H1WA—O1—H1WB	103.8	N2—C10—C9	120.40 (18)
Fe1—O2—H2WA	129.5	N2—C10—H10	119.8
Fe1—O2—H2WB	124.8	C9—C10—H10	119.8
H2WA—O2—H2WB	104.3	N2—C11—C12	119.85 (17)
Fe1—O3—H3WA	129.3	N2—C11—H11	120.1
Fe1—O3—H3WB	122.0	C12—C11—H11	120.1
H3WA—O3—H3WB	104.3	C11—C12—C8	120.17 (18)
Fe1—O4—H4WA	123.2	C11—C12—H12	119.9
Fe1—O4—H4WB	128.2	C8—C12—H12	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1X···O13	0.89	1.74	2.622 (2)	173
N2—H2X···O10ⁱ	0.89	1.75	2.631 (2)	170
O1—H1WB···O7	0.85	1.89	2.733 (2)	175
O1—H1WA···O9ⁱⁱ	0.85	1.90	2.741 (2)	170
O2—H2WA···O8	0.85	1.90	2.719 (2)	161
O2—H2WB···O12	0.85	1.86	2.711 (2)	175
O3—H3WA···O8ⁱⁱ	0.85	1.91	2.751 (2)	169
O3—H3WB···O11	0.85	1.88	2.726 (2)	174
O4—H4WA···O11ⁱⁱⁱ	0.85	1.85	2.696 (2)	171
O4—H4WB···O12^iv	0.85	1.86	2.710 (2)	175
O5—H5WA···O15	0.85	1.90	2.742 (2)	169
O5—H5WB···O14ⁱⁱⁱ	0.85	1.90	2.750 (2)	175
O6—H6WA···O15^v	0.85	1.93	2.763 (2)	165
O6—H6WB···O14^iv	0.85	1.89	2.739 (2)	180
O15—H15A···O9ⁱⁱ	0.85	1.97	2.780 (2)	159
O15—H15B···O7^vi	0.85	1.92	2.7628 (19)	174
C1—H1···O8^vii	0.95	2.48	3.339 (3)	150
C1—H1···O10^vii	0.95	2.31	3.172 (2)	150
C11—H11···O13^viii	0.95	2.34	3.189 (2)	149
C11—H11···O14^viii	0.95	2.43	3.291 (3)	151

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1X···O13	0.89	1.74	2.622 (2)	173
N2—H2X···O10ⁱ	0.89	1.75	2.631 (2)	170
O1—H1WB···O7	0.85	1.89	2.733 (2)	175
O1—H1WA···O9ⁱⁱ	0.85	1.90	2.741 (2)	170
O2—H2WA···O8	0.85	1.90	2.719 (2)	161
O2—H2WB···O12	0.85	1.86	2.711 (2)	175
O3—H3WA···O8ⁱⁱ	0.85	1.91	2.751 (2)	169
O3—H3WB···O11	0.85	1.88	2.726 (2)	174
O4—H4WA···O11ⁱⁱⁱ	0.85	1.85	2.696 (2)	171
O4—H4WB···O12^iv	0.85	1.86	2.710 (2)	175
O5—H5WA···O15	0.85	1.90	2.742 (2)	169
O5—H5WB···O14ⁱⁱⁱ	0.85	1.90	2.750 (2)	175
O6—H6WA···O15^v	0.85	1.93	2.763 (2)	165
O6—H6WB···O14^iv	0.85	1.89	2.739 (2)	180
O15—H15A···O9ⁱⁱ	0.85	1.97	2.780 (2)	159
O15—H15B···O7^vi	0.85	1.92	2.7628 (19)	174
C1—H1···O8^vii	0.95	2.48	3.339 (3)	150
C1—H1···O10^vii	0.95	2.31	3.172 (2)	150
C11—H11···O13^viii	0.95	2.34	3.189 (2)	149
C11—H11···O14^viii	0.95	2.43	3.291 (3)	151

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

References

Bok, L. D. C., Leipoldt, J. G. & Basson, S. S. (1975). Z. Anorg. Allg. Chem. 415, 81–83. CrossRef CAS Web of Science Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal ImpactGbR, Bonn, Germany. Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Prakash, M. J., Oliver, A. G. & Sevov, S. C. (2012). Cryst. Growth Des. 12, 2684–2690. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 5| May 2014| Page m169

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1:1 Co-crystal of 4,4′-(ethene-1,2-di­yl)dipyridin-1-ium sulfate and hexa­aqua­iron(II) sulfate monohydrate

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metal-organic compounds

1:1 Co-crystal of 4,4′-(ethene-1,2-diyl)dipyridin-1-ium sulfate and hexaaquairon(II) sulfate monohydrate