Crystal structure of catena-poly[[[tetra­aqua­iron(II)]-trans-μ-1,2-bis­(pyridin-4-yl)ethene-κ²N:N′] bis­(p-toluene­sulfonate) methanol disolvate]

The 1,2-bis­(pyridin-4-yl)ethene mol­ecules bridge Fe^II cations to form polymeric chains running along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.097
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.375 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         37 Report

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          1 Info
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          7 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        69% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

catena-Poly[[[tetraaquairon(II)]-trans-µ-1,2-bis(pyridin-4-yl)ethene-κ²N:N'] bis(p-toluenesulfonate) methanol disolvate]

Crystal data

[Fe(C12H10N2)(H2O)4](C7H7O3S)2·2CH4O	F(000) = 752
Mr = 716.59	Dx = 1.453 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.8416 (9) Å	Cell parameters from 2979 reflections
b = 7.7686 (4) Å	θ = 2.6–31.1°
c = 16.4076 (13) Å	µ = 0.65 mm^−1
β = 111.845 (9)°	T = 200 K
V = 1637.6 (2) Å^3	Prism, clear intense red
Z = 2	0.35 × 0.2 × 0.15 mm

Data collection

Rigaku OD Xcalibur, Eos diffractometer	2363 reflections with I > 2σ(I)
Detector resolution: 8.0797 pixels mm^-1	Rint = 0.030
ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −16→16
Tmin = 0.920, Tmax = 1.000	k = −8→9
6379 measured reflections	l = −19→11
2857 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0396P)^2 + 0.6283P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2857 reflections	Δρmax = 0.24 e Å^−3
227 parameters	Δρmin = −0.32 e Å^−3
7 restraints

Special details

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.

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

	x	y	z	Uiso*/Ueq
Fe1	0.000000	0.500000	0.500000	0.01832 (16)
O2	0.07337 (15)	0.5517 (3)	0.63317 (12)	0.0295 (5)
O1	−0.00268 (15)	0.2362 (2)	0.53062 (14)	0.0279 (4)
O6	0.06975 (17)	0.3317 (3)	0.75578 (14)	0.0403 (5)
N1	0.15498 (16)	0.4896 (2)	0.48932 (14)	0.0218 (5)
C1	0.23952 (19)	0.4220 (3)	0.55153 (18)	0.0243 (6)
H1	0.231285	0.368884	0.600701	0.029*
C3	0.3528 (2)	0.5005 (3)	0.47719 (17)	0.0235 (6)
C2	0.3375 (2)	0.4249 (3)	0.54841 (18)	0.0269 (6)
H2	0.394535	0.375488	0.594749	0.032*
C4	0.2643 (2)	0.5672 (3)	0.41120 (17)	0.0256 (6)
H4	0.269716	0.617840	0.360394	0.031*
C6	0.4539 (2)	0.5179 (3)	0.46934 (18)	0.0251 (6)
H6	0.453831	0.558952	0.414775	0.030*
C5	0.1695 (2)	0.5594 (3)	0.41982 (17)	0.0246 (6)
H5	0.110758	0.606167	0.374029	0.029*
C14	0.0849 (3)	0.3932 (4)	0.8412 (2)	0.0470 (8)
H14A	0.159070	0.415178	0.873617	0.071*
H14B	0.060297	0.306700	0.872498	0.071*
H14C	0.045634	0.500216	0.836491	0.071*
S1	0.22227 (5)	0.97890 (8)	0.66335 (4)	0.02490 (18)
O3	0.14978 (14)	0.9925 (2)	0.57179 (12)	0.0310 (5)
O5	0.21658 (15)	0.8109 (2)	0.70032 (13)	0.0336 (5)
O4	0.21348 (15)	1.1211 (2)	0.71723 (13)	0.0362 (5)
C7	0.3476 (2)	0.9925 (3)	0.65937 (17)	0.0225 (6)
C8	0.4272 (2)	1.0780 (3)	0.72377 (17)	0.0283 (6)
H8	0.413993	1.136967	0.769296	0.034*
C11	0.4661 (2)	0.9110 (3)	0.59080 (19)	0.0312 (7)
H11	0.478876	0.854123	0.544533	0.037*
C9	0.5267 (2)	1.0775 (3)	0.72171 (18)	0.0309 (7)
H9	0.581277	1.136606	0.766118	0.037*
C12	0.3668 (2)	0.9108 (3)	0.59167 (18)	0.0298 (6)
H12	0.311753	0.855117	0.546108	0.036*
C10	0.5476 (2)	0.9924 (3)	0.65615 (19)	0.0292 (6)
C13	0.6567 (2)	0.9835 (4)	0.6563 (2)	0.0413 (8)
H13A	0.653625	0.983917	0.595625	0.062*
H13B	0.690467	0.877556	0.685580	0.062*
H13C	0.696653	1.083302	0.687642	0.062*
H2A	0.078 (3)	0.485 (3)	0.6748 (17)	0.061 (12)*
H2B	0.113 (2)	0.633 (3)	0.6576 (18)	0.042 (9)*
H1A	−0.0508 (17)	0.176 (3)	0.4972 (17)	0.043 (10)*
H1B	0.0490 (17)	0.171 (3)	0.5494 (19)	0.043 (9)*
H6A	0.120 (2)	0.256 (4)	0.756 (2)	0.061 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0129 (3)	0.0212 (3)	0.0211 (3)	−0.0002 (2)	0.0065 (2)	0.0006 (2)
O2	0.0277 (11)	0.0355 (11)	0.0217 (11)	−0.0106 (9)	0.0052 (9)	−0.0011 (9)
O1	0.0181 (10)	0.0212 (10)	0.0383 (12)	0.0007 (8)	0.0035 (9)	0.0010 (9)
O6	0.0434 (13)	0.0432 (12)	0.0396 (13)	0.0106 (10)	0.0215 (11)	0.0085 (10)
N1	0.0183 (11)	0.0229 (11)	0.0252 (12)	−0.0008 (9)	0.0092 (10)	0.0004 (9)
C1	0.0196 (14)	0.0281 (14)	0.0271 (14)	0.0022 (11)	0.0108 (12)	0.0068 (11)
C3	0.0218 (14)	0.0230 (13)	0.0281 (15)	−0.0009 (11)	0.0119 (12)	−0.0046 (11)
C2	0.0170 (13)	0.0324 (14)	0.0296 (16)	0.0036 (11)	0.0068 (12)	0.0071 (12)
C4	0.0247 (14)	0.0309 (14)	0.0246 (14)	−0.0020 (11)	0.0130 (12)	−0.0002 (11)
C6	0.0231 (13)	0.0281 (14)	0.0296 (15)	−0.0007 (11)	0.0161 (12)	−0.0003 (12)
C5	0.0176 (13)	0.0307 (14)	0.0248 (15)	0.0017 (11)	0.0071 (12)	0.0025 (12)
C14	0.051 (2)	0.052 (2)	0.047 (2)	−0.0027 (17)	0.0281 (18)	0.0034 (16)
S1	0.0210 (4)	0.0225 (3)	0.0289 (4)	0.0001 (3)	0.0066 (3)	−0.0020 (3)
O3	0.0209 (10)	0.0340 (10)	0.0309 (11)	0.0040 (8)	0.0014 (9)	0.0018 (9)
O5	0.0293 (11)	0.0295 (10)	0.0376 (12)	−0.0057 (9)	0.0074 (9)	0.0040 (9)
O4	0.0340 (11)	0.0359 (11)	0.0415 (12)	0.0006 (9)	0.0173 (10)	−0.0112 (9)
C7	0.0233 (14)	0.0162 (12)	0.0241 (14)	0.0016 (10)	0.0043 (11)	0.0009 (10)
C8	0.0286 (15)	0.0254 (14)	0.0272 (15)	−0.0014 (11)	0.0062 (13)	−0.0059 (12)
C11	0.0314 (16)	0.0286 (14)	0.0364 (17)	0.0003 (12)	0.0158 (14)	−0.0047 (12)
C9	0.0227 (15)	0.0274 (14)	0.0328 (16)	−0.0051 (11)	−0.0011 (13)	−0.0023 (12)
C12	0.0238 (15)	0.0287 (14)	0.0320 (16)	−0.0025 (12)	0.0048 (13)	−0.0089 (12)
C10	0.0263 (15)	0.0227 (13)	0.0351 (16)	0.0013 (11)	0.0073 (13)	0.0046 (12)
C13	0.0247 (16)	0.0435 (18)	0.053 (2)	−0.0018 (13)	0.0116 (15)	0.0061 (15)

Geometric parameters (Å, º)

Fe1—O1	2.1135 (18)	C6—H6	0.9500
Fe1—O1^i	2.1135 (18)	C5—H5	0.9500
Fe1—O2	2.0773 (19)	C14—H14A	0.9800
Fe1—O2^i	2.0773 (19)	C14—H14B	0.9800
Fe1—N1^i	2.218 (2)	C14—H14C	0.9800
Fe1—N1	2.218 (2)	S1—O3	1.4673 (19)
O2—H2A	0.839 (17)	S1—O5	1.4535 (19)
O2—H2B	0.839 (17)	S1—O4	1.4482 (19)
O1—H1A	0.832 (17)	S1—C7	1.764 (3)
O1—H1B	0.837 (17)	C7—C8	1.380 (4)
O6—C14	1.421 (4)	C7—C12	1.387 (4)
O6—H6A	0.910 (18)	C8—H8	0.9500
N1—C1	1.341 (3)	C8—C9	1.391 (4)
N1—C5	1.344 (3)	C11—H11	0.9500
C1—H1	0.9500	C11—C12	1.380 (4)
C1—C2	1.376 (3)	C11—C10	1.386 (4)
C3—C2	1.393 (4)	C9—H9	0.9500
C3—C4	1.398 (4)	C9—C10	1.382 (4)
C3—C6	1.459 (4)	C12—H12	0.9500
C2—H2	0.9500	C10—C13	1.511 (4)
C4—H4	0.9500	C13—H13A	0.9800
C4—C5	1.372 (3)	C13—H13B	0.9800
C6—C6^ii	1.327 (5)	C13—H13C	0.9800
O2—Fe1—O2^i	180.00 (11)	N1—C5—C4	123.8 (2)
O2^i—Fe1—O1^i	88.98 (8)	N1—C5—H5	118.1
O2^i—Fe1—O1	91.02 (8)	C4—C5—H5	118.1
O2—Fe1—O1^i	91.01 (8)	O6—C14—H14A	109.5
O2—Fe1—O1	88.98 (8)	O6—C14—H14B	109.5
O2^i—Fe1—N1	91.06 (8)	O6—C14—H14C	109.5
O2^i—Fe1—N1^i	88.94 (8)	H14A—C14—H14B	109.5
O2—Fe1—N1^i	91.06 (8)	H14A—C14—H14C	109.5
O2—Fe1—N1	88.94 (8)	H14B—C14—H14C	109.5
O1^i—Fe1—O1	180.0	O3—S1—C7	105.38 (12)
O1—Fe1—N1	94.96 (7)	O5—S1—O3	111.68 (11)
O1—Fe1—N1^i	85.04 (7)	O5—S1—C7	106.02 (11)
O1^i—Fe1—N1^i	94.96 (7)	O4—S1—O3	112.92 (11)
O1^i—Fe1—N1	85.04 (7)	O4—S1—O5	113.58 (12)
N1—Fe1—N1^i	180.0	O4—S1—C7	106.52 (12)
Fe1—O2—H2A	127 (2)	C8—C7—S1	121.1 (2)
Fe1—O2—H2B	129 (2)	C8—C7—C12	119.8 (3)
H2A—O2—H2B	104 (3)	C12—C7—S1	119.1 (2)
Fe1—O1—H1A	118 (2)	C7—C8—H8	120.2
Fe1—O1—H1B	126 (2)	C7—C8—C9	119.7 (3)
H1A—O1—H1B	105 (3)	C9—C8—H8	120.2
C14—O6—H6A	113 (2)	C12—C11—H11	119.4
C1—N1—Fe1	123.36 (17)	C12—C11—C10	121.3 (3)
C1—N1—C5	116.1 (2)	C10—C11—H11	119.4
C5—N1—Fe1	120.44 (17)	C8—C9—H9	119.5
N1—C1—H1	118.0	C10—C9—C8	121.1 (3)
N1—C1—C2	123.9 (2)	C10—C9—H9	119.5
C2—C1—H1	118.0	C7—C12—H12	120.1
C2—C3—C4	116.3 (2)	C11—C12—C7	119.7 (3)
C2—C3—C6	124.3 (2)	C11—C12—H12	120.1
C4—C3—C6	119.4 (2)	C11—C10—C13	120.3 (3)
C1—C2—C3	119.9 (2)	C9—C10—C11	118.3 (3)
C1—C2—H2	120.1	C9—C10—C13	121.3 (3)
C3—C2—H2	120.1	C10—C13—H13A	109.5
C3—C4—H4	120.0	C10—C13—H13B	109.5
C5—C4—C3	120.0 (2)	C10—C13—H13C	109.5
C5—C4—H4	120.0	H13A—C13—H13B	109.5
C3—C6—H6	116.7	H13A—C13—H13C	109.5
C6^ii—C6—C3	126.6 (3)	H13B—C13—H13C	109.5
C6^ii—C6—H6	116.7

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3^i	0.83 (2)	1.93 (2)	2.753 (3)	172 (3)
O1—H1B···O3^iii	0.84 (2)	1.90 (2)	2.726 (2)	168 (3)
O2—H2A···O6	0.84 (2)	1.82 (2)	2.654 (3)	172 (3)
O2—H2B···O5	0.84 (2)	1.92 (2)	2.752 (3)	170 (3)
O6—H6A···O4^iii	0.91 (2)	1.95 (2)	2.823 (3)	161 (3)
C4—H4···O5^iv	0.95	2.51	3.406 (3)	157
C13—H13B···O4^v	0.98	2.59	3.562 (4)	172
C13—H13C···O5^vi	0.98	2.51	3.465 (4)	165

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