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Two new diamagnetic coordination compounds, [Fe(phen)3][C(CN)3]2, (I), and [Fe(bpy)3][C(CN)3]2·1.5H2O, (II), have been synthesized and characterized by single-crystal X-ray diffraction analysis, and IR and UV–Vis spectroscopy (phen is 1,10-phenanthroline, C12H8N2, and bpy is 2,2′-bi­pyridine, C10H8N2). Both com­pounds are ionic with distorted octa­hedral [Fe(phen)3]2+ or [Fe(bpy)3]2+ complex cations, with average Fe—N distances of 1.977 (2) and 1.971 (3) Å, respectively, and two uncoordinated planar tri­cyano­methanide, or [C(CN)3], counter-anions bal­ancing the positive charges of the cations. Solvent water mol­ecules and tcm anions in (II) are linked via O—H...N hydrogen bonds into negatively charged layers and the inter­layer space is filled by [Fe(bpy)3]2+ cations. The structures of (I) and (II) are stabilized by π–π inter­actions between the stacked aromatic rings of the phen ligands of two adjacent cations and by O—H...N hydrogen bonds, respectively, and also by π–π stacking inter­actions between phen and tcm units in (I).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614006512/em3067sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614006512/em3067Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614006512/em3067IIsup3.hkl
Contains datablock II

CCDC references: 993434; 993435

Computing details top

For both structures, data collection: WinExpose in X-AREA (Stoe & Cie, 2002); cell refinement: WinCell in X-AREA (Stoe & Cie, 2002); data reduction: WinIntegrate in X-AREA (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008).

Tris(1,10-phenanthroline-κ2N,N')iron(II) bis(tricyanomethanide) (I) top
Crystal data top
[Fe(C12H8N2)3](C4N3)2F(000) = 1592
Mr = 776.60Dx = 1.427 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
a = 9.3618 (5) ÅCell parameters from 20688 reflections
b = 30.6516 (14) Åθ = 1.8–29.5°
c = 12.5952 (8) ŵ = 0.47 mm1
β = 90.683 (5)°T = 193 K
V = 3614.0 (3) Å3Prism, dark red
Z = 40.11 × 0.11 × 0.10 mm
Data collection top
Stoe IPDSII
diffractometer
5624 reflections with I > 2σ(I)
ω scansRint = 0.039
Absorption correction: numerical
(XPREP in SHELXTL; Sheldrick, 2008)
θmax = 26.5°, θmin = 1.8°
Tmin = 0.843, Tmax = 0.926h = 1111
27223 measured reflectionsk = 3838
7492 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0328P)2]
where P = (Fo2 + 2Fc2)/3
7492 reflections(Δ/σ)max = 0.001
520 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.32 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Fe10.55637 (2)0.11933 (2)0.73383 (2)0.02313 (6)
N100.65910 (13)0.10485 (4)0.86705 (9)0.0247 (3)
N200.51520 (13)0.05610 (4)0.73296 (9)0.0252 (3)
N300.38084 (14)0.13332 (4)0.81261 (10)0.0264 (3)
N400.58829 (14)0.18291 (4)0.74655 (10)0.0277 (3)
N500.46751 (14)0.13060 (4)0.59297 (10)0.0270 (3)
N600.72861 (14)0.10868 (4)0.64813 (10)0.0265 (3)
C110.65446 (16)0.06141 (5)0.89074 (11)0.0255 (3)
C120.73437 (17)0.13043 (5)0.93300 (12)0.0294 (3)
H120.73960.16080.91800.035*
C130.80581 (18)0.11444 (6)1.02315 (12)0.0346 (4)
H130.85770.13381.06810.041*
C140.80077 (18)0.07083 (6)1.04642 (13)0.0352 (4)
H140.84870.05981.10760.042*
C150.72384 (17)0.04255 (5)0.97869 (12)0.0303 (3)
C160.71353 (19)0.00371 (5)0.99315 (13)0.0360 (4)
H160.76090.01691.05200.043*
C210.57622 (16)0.03478 (5)0.81770 (11)0.0251 (3)
C220.44028 (18)0.03219 (5)0.66375 (13)0.0328 (4)
H220.39830.04620.60380.039*
C230.4211 (2)0.01279 (5)0.67599 (14)0.0402 (4)
H230.36520.02860.62570.048*
C240.4829 (2)0.03398 (5)0.76043 (13)0.0386 (4)
H240.47060.06450.76890.046*
C250.56477 (18)0.01018 (5)0.83453 (12)0.0304 (3)
C260.63755 (19)0.02896 (5)0.92453 (13)0.0360 (4)
H260.63240.05950.93610.043*
C310.36801 (17)0.17667 (5)0.83462 (12)0.0283 (3)
C320.27761 (18)0.10704 (5)0.84723 (13)0.0331 (4)
H320.28370.07680.83180.040*
C330.16158 (19)0.12196 (6)0.90484 (15)0.0429 (4)
H330.09190.10190.92930.051*
C340.1479 (2)0.16542 (6)0.92629 (15)0.0464 (5)
H340.06860.17580.96530.056*
C350.25242 (19)0.19461 (6)0.88988 (14)0.0374 (4)
C360.2493 (2)0.24074 (6)0.90564 (17)0.0510 (5)
H360.17220.25350.94290.061*
C410.47959 (17)0.20372 (5)0.79708 (12)0.0284 (3)
C420.69335 (19)0.20759 (5)0.70878 (14)0.0369 (4)
H420.77080.19380.67400.044*
C430.6936 (2)0.25311 (6)0.71848 (15)0.0453 (5)
H430.76990.26960.68970.054*
C440.5852 (2)0.27385 (6)0.76900 (15)0.0453 (5)
H440.58520.30470.77530.054*
C450.4737 (2)0.24909 (5)0.81167 (14)0.0377 (4)
C460.3545 (2)0.26650 (6)0.86829 (17)0.0507 (5)
H460.34940.29710.87990.061*
C510.56352 (17)0.12778 (5)0.51211 (11)0.0267 (3)
C520.33459 (18)0.14250 (5)0.56701 (13)0.0343 (4)
H520.26600.14480.62170.041*
C530.2918 (2)0.15172 (6)0.46238 (14)0.0412 (4)
H530.19580.16000.44750.049*
C540.3876 (2)0.14890 (6)0.38159 (13)0.0390 (4)
H540.35900.15510.31060.047*
C550.52884 (18)0.13677 (5)0.40527 (12)0.0313 (4)
C560.6394 (2)0.13198 (5)0.32783 (13)0.0353 (4)
H560.61900.13870.25560.042*
C610.70413 (16)0.11476 (5)0.54171 (11)0.0264 (3)
C620.85816 (17)0.09536 (5)0.67781 (13)0.0319 (4)
H620.87740.09110.75130.038*
C630.96753 (19)0.08726 (6)0.60545 (14)0.0376 (4)
H631.05780.07700.63000.045*
C640.94392 (19)0.09415 (5)0.49967 (14)0.0368 (4)
H641.01800.08920.45020.044*
C650.80927 (18)0.10867 (5)0.46456 (12)0.0307 (4)
C660.77202 (19)0.11813 (5)0.35566 (12)0.0363 (4)
H660.84190.11460.30230.044*
C10.89240 (19)0.03417 (6)0.71828 (14)0.0388 (4)
C20.9753 (2)0.00248 (6)0.77134 (15)0.0464 (5)
N21.0423 (2)0.02325 (6)0.81577 (16)0.0692 (6)
C30.8157 (2)0.02292 (7)0.62522 (16)0.0491 (5)
N30.7544 (2)0.01431 (7)0.54861 (16)0.0752 (6)
C40.8888 (2)0.07696 (7)0.75797 (14)0.0408 (4)
N40.8900 (2)0.11228 (6)0.78832 (14)0.0580 (5)
C50.6279 (2)0.23478 (7)1.08715 (16)0.0480 (5)
C60.560 (2)0.2752 (7)1.0993 (10)0.049 (2)0.5
C6A0.578 (2)0.2748 (7)1.1324 (10)0.049 (2)0.5
N60.5113 (14)0.3091 (5)1.1153 (7)0.074 (2)0.5
N6A0.5349 (14)0.3074 (5)1.1630 (7)0.074 (2)0.5
C70.7709 (2)0.23323 (7)1.05501 (18)0.0541 (5)
N70.8877 (2)0.23200 (7)1.0286 (2)0.0838 (7)
C80.5449 (2)0.19672 (7)1.09071 (14)0.0451 (5)
N80.4783 (2)0.16503 (7)1.09364 (14)0.0603 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.02155 (11)0.02257 (10)0.02527 (10)0.00107 (9)0.00007 (7)0.00098 (9)
N100.0233 (7)0.0254 (6)0.0255 (6)0.0007 (5)0.0024 (5)0.0005 (5)
N200.0248 (7)0.0257 (6)0.0253 (6)0.0011 (5)0.0007 (5)0.0014 (5)
N300.0249 (7)0.0263 (6)0.0281 (6)0.0021 (5)0.0004 (5)0.0030 (5)
N400.0272 (7)0.0263 (7)0.0297 (7)0.0009 (5)0.0015 (5)0.0019 (5)
N500.0252 (7)0.0240 (6)0.0317 (7)0.0006 (5)0.0009 (5)0.0036 (5)
N600.0262 (7)0.0252 (6)0.0281 (6)0.0014 (5)0.0003 (5)0.0005 (5)
C110.0232 (8)0.0273 (8)0.0260 (7)0.0016 (6)0.0019 (6)0.0010 (6)
C120.0301 (9)0.0271 (8)0.0311 (8)0.0012 (7)0.0007 (6)0.0033 (6)
C130.0324 (9)0.0394 (9)0.0317 (8)0.0034 (8)0.0051 (7)0.0037 (7)
C140.0325 (10)0.0435 (9)0.0295 (8)0.0016 (8)0.0081 (7)0.0025 (7)
C150.0282 (9)0.0339 (8)0.0287 (8)0.0010 (7)0.0011 (6)0.0030 (6)
C160.0389 (10)0.0353 (9)0.0336 (9)0.0044 (8)0.0057 (7)0.0089 (7)
C210.0234 (8)0.0254 (7)0.0266 (7)0.0022 (6)0.0007 (6)0.0005 (6)
C220.0357 (10)0.0317 (8)0.0307 (8)0.0006 (7)0.0064 (7)0.0006 (6)
C230.0488 (11)0.0315 (9)0.0400 (9)0.0079 (8)0.0092 (8)0.0061 (7)
C240.0495 (12)0.0248 (8)0.0413 (10)0.0029 (8)0.0034 (8)0.0012 (7)
C250.0332 (9)0.0262 (8)0.0318 (8)0.0021 (7)0.0006 (7)0.0006 (6)
C260.0408 (10)0.0275 (8)0.0396 (9)0.0026 (8)0.0012 (7)0.0075 (7)
C310.0288 (9)0.0277 (8)0.0284 (8)0.0052 (7)0.0016 (6)0.0011 (6)
C320.0298 (9)0.0307 (8)0.0387 (9)0.0008 (7)0.0040 (7)0.0039 (7)
C330.0316 (10)0.0474 (10)0.0499 (10)0.0012 (9)0.0119 (8)0.0047 (9)
C340.0328 (10)0.0527 (12)0.0539 (11)0.0088 (9)0.0142 (8)0.0029 (9)
C350.0321 (10)0.0388 (9)0.0413 (9)0.0085 (8)0.0028 (7)0.0040 (7)
C360.0470 (12)0.0412 (11)0.0649 (13)0.0162 (9)0.0068 (10)0.0120 (9)
C410.0305 (9)0.0249 (7)0.0298 (8)0.0042 (7)0.0041 (6)0.0004 (6)
C420.0352 (10)0.0339 (9)0.0417 (10)0.0076 (8)0.0028 (7)0.0015 (7)
C430.0469 (12)0.0341 (9)0.0548 (11)0.0148 (9)0.0014 (9)0.0041 (8)
C440.0552 (13)0.0251 (8)0.0554 (11)0.0053 (8)0.0102 (9)0.0012 (8)
C450.0434 (11)0.0255 (8)0.0439 (10)0.0038 (8)0.0089 (8)0.0002 (7)
C460.0549 (13)0.0275 (9)0.0695 (13)0.0123 (9)0.0025 (10)0.0096 (9)
C510.0311 (9)0.0220 (8)0.0271 (7)0.0032 (6)0.0002 (6)0.0000 (6)
C520.0284 (9)0.0368 (9)0.0377 (9)0.0032 (7)0.0024 (7)0.0069 (7)
C530.0320 (10)0.0471 (10)0.0444 (10)0.0021 (8)0.0106 (8)0.0108 (8)
C540.0442 (11)0.0404 (10)0.0323 (9)0.0048 (8)0.0103 (8)0.0086 (7)
C550.0388 (10)0.0249 (7)0.0299 (8)0.0058 (7)0.0051 (7)0.0020 (6)
C560.0499 (11)0.0308 (8)0.0250 (8)0.0091 (8)0.0002 (7)0.0007 (6)
C610.0292 (8)0.0223 (7)0.0276 (7)0.0017 (6)0.0014 (6)0.0009 (6)
C620.0271 (9)0.0336 (9)0.0348 (9)0.0038 (7)0.0004 (7)0.0008 (7)
C630.0265 (9)0.0400 (9)0.0463 (10)0.0065 (8)0.0040 (7)0.0001 (8)
C640.0319 (10)0.0379 (9)0.0409 (9)0.0013 (8)0.0114 (7)0.0052 (7)
C650.0346 (9)0.0257 (8)0.0320 (8)0.0041 (7)0.0056 (7)0.0047 (6)
C660.0455 (10)0.0329 (8)0.0306 (8)0.0080 (8)0.0084 (7)0.0034 (7)
C10.0345 (10)0.0443 (10)0.0375 (9)0.0072 (8)0.0071 (7)0.0084 (8)
C20.0503 (13)0.0395 (10)0.0490 (11)0.0095 (9)0.0195 (9)0.0037 (8)
N20.0880 (15)0.0439 (10)0.0747 (13)0.0050 (10)0.0487 (11)0.0082 (9)
C30.0419 (11)0.0579 (12)0.0473 (11)0.0067 (10)0.0097 (9)0.0117 (9)
N30.0734 (14)0.0923 (15)0.0592 (12)0.0065 (12)0.0312 (11)0.0060 (11)
C40.0330 (10)0.0493 (11)0.0402 (10)0.0014 (8)0.0009 (8)0.0126 (8)
N40.0614 (12)0.0485 (11)0.0642 (11)0.0063 (9)0.0021 (9)0.0048 (9)
C50.0374 (11)0.0539 (12)0.0529 (12)0.0118 (9)0.0040 (9)0.0030 (9)
C60.031 (4)0.0544 (14)0.062 (7)0.006 (3)0.003 (5)0.002 (6)
C6A0.031 (4)0.0544 (14)0.062 (7)0.006 (3)0.003 (5)0.002 (6)
N60.048 (4)0.0540 (16)0.122 (7)0.008 (2)0.026 (5)0.000 (5)
N6A0.048 (4)0.0540 (16)0.122 (7)0.008 (2)0.026 (5)0.000 (5)
C70.0438 (13)0.0524 (12)0.0660 (14)0.0096 (10)0.0005 (10)0.0162 (10)
N70.0464 (12)0.0772 (14)0.128 (2)0.0102 (11)0.0171 (12)0.0346 (13)
C80.0438 (12)0.0561 (12)0.0353 (10)0.0131 (10)0.0001 (8)0.0033 (8)
N80.0586 (12)0.0691 (13)0.0532 (11)0.0035 (10)0.0015 (9)0.0075 (9)
Geometric parameters (Å, º) top
Fe1—N101.9745 (12)C35—C361.428 (3)
Fe1—N201.9761 (12)C36—C461.351 (3)
Fe1—N301.9767 (13)C36—H360.9500
Fe1—N401.9779 (13)C41—C451.404 (2)
Fe1—N601.9782 (13)C42—C431.401 (2)
Fe1—N501.9810 (13)C42—H420.9500
N10—C121.3369 (19)C43—C441.362 (3)
N10—C111.3654 (19)C43—H430.9500
N20—C221.332 (2)C44—C451.403 (3)
N20—C211.3704 (19)C44—H440.9500
N30—C321.336 (2)C45—C461.434 (3)
N30—C311.3628 (19)C46—H460.9500
N40—C421.333 (2)C51—C551.408 (2)
N40—C411.365 (2)C51—C611.421 (2)
N50—C521.334 (2)C52—C531.402 (2)
N50—C511.3691 (19)C52—H520.9500
N60—C621.329 (2)C53—C541.367 (3)
N60—C611.3700 (19)C53—H530.9500
C11—C151.402 (2)C54—C551.402 (2)
C11—C211.426 (2)C54—H540.9500
C12—C131.400 (2)C55—C561.438 (2)
C12—H120.9500C56—C661.354 (3)
C13—C141.370 (2)C56—H560.9500
C13—H130.9500C61—C651.404 (2)
C14—C151.408 (2)C62—C631.401 (2)
C14—H140.9500C62—H620.9500
C15—C161.433 (2)C63—C641.364 (2)
C16—C261.356 (2)C63—H630.9500
C16—H160.9500C64—C651.403 (2)
C21—C251.399 (2)C64—H640.9500
C22—C231.399 (2)C65—C661.441 (2)
C22—H220.9500C66—H660.9500
C23—C241.368 (2)C1—C41.404 (3)
C23—H230.9500C1—C21.407 (3)
C24—C251.405 (2)C1—C31.410 (3)
C24—H240.9500C2—N21.149 (2)
C25—C261.436 (2)C3—N31.148 (3)
C26—H260.9500C4—N41.148 (2)
C31—C351.406 (2)C5—C61.40 (2)
C31—C411.419 (2)C5—C81.403 (3)
C32—C331.391 (2)C5—C71.404 (3)
C32—H320.9500C5—C6A1.43 (2)
C33—C341.366 (3)C6—N61.15 (2)
C33—H330.9500C6A—N6A1.15 (2)
C34—C351.407 (3)C7—N71.147 (3)
C34—H340.9500C8—N81.155 (3)
N10—Fe1—N2082.96 (5)C33—C34—C35119.23 (16)
N10—Fe1—N3091.24 (5)C33—C34—H34120.4
N20—Fe1—N3093.00 (5)C35—C34—H34120.4
N10—Fe1—N4094.65 (5)C31—C35—C34117.08 (16)
N20—Fe1—N40174.97 (5)C31—C35—C36118.26 (17)
N30—Fe1—N4082.60 (5)C34—C35—C36124.66 (17)
N10—Fe1—N6091.98 (5)C46—C36—C35120.91 (18)
N20—Fe1—N6089.73 (5)C46—C36—H36119.5
N30—Fe1—N60176.01 (5)C35—C36—H36119.5
N40—Fe1—N6094.79 (5)N40—C41—C45123.68 (15)
N10—Fe1—N50174.50 (5)N40—C41—C31116.00 (13)
N20—Fe1—N5094.95 (5)C45—C41—C31120.32 (15)
N30—Fe1—N5093.95 (5)N40—C42—C43122.33 (17)
N40—Fe1—N5087.83 (5)N40—C42—H42118.8
N60—Fe1—N5082.90 (5)C43—C42—H42118.8
C12—N10—C11117.01 (13)C44—C43—C42120.34 (17)
C12—N10—Fe1130.09 (10)C44—C43—H43119.8
C11—N10—Fe1112.86 (10)C42—C43—H43119.8
C22—N20—C21117.31 (13)C43—C44—C45119.26 (16)
C22—N20—Fe1130.12 (11)C43—C44—H44120.4
C21—N20—Fe1112.57 (9)C45—C44—H44120.4
C32—N30—C31117.12 (14)C44—C45—C41117.06 (16)
C32—N30—Fe1129.95 (11)C44—C45—C46125.19 (16)
C31—N30—Fe1112.92 (10)C41—C45—C46117.75 (16)
C42—N40—C41117.31 (14)C36—C46—C45122.04 (17)
C42—N40—Fe1129.91 (11)C36—C46—H46119.0
C41—N40—Fe1112.67 (10)C45—C46—H46119.0
C52—N50—C51116.99 (13)N50—C51—C55123.56 (15)
C52—N50—Fe1130.39 (11)N50—C51—C61115.91 (13)
C51—N50—Fe1112.51 (10)C55—C51—C61120.53 (14)
C62—N60—C61117.29 (13)N50—C52—C53122.74 (16)
C62—N60—Fe1130.11 (11)N50—C52—H52118.6
C61—N60—Fe1112.55 (10)C53—C52—H52118.6
N10—C11—C15124.00 (14)C54—C53—C52120.30 (16)
N10—C11—C21115.77 (13)C54—C53—H53119.8
C15—C11—C21120.21 (14)C52—C53—H53119.8
N10—C12—C13122.81 (14)C53—C54—C55118.93 (15)
N10—C12—H12118.6C53—C54—H54120.5
C13—C12—H12118.6C55—C54—H54120.5
C14—C13—C12119.88 (15)C54—C55—C51117.47 (15)
C14—C13—H13120.1C54—C55—C56124.57 (15)
C12—C13—H13120.1C51—C55—C56117.94 (15)
C13—C14—C15119.33 (15)C66—C56—C55121.44 (15)
C13—C14—H14120.3C66—C56—H56119.3
C15—C14—H14120.3C55—C56—H56119.3
C11—C15—C14116.97 (14)N60—C61—C65123.27 (14)
C11—C15—C16118.50 (15)N60—C61—C51116.01 (13)
C14—C15—C16124.53 (15)C65—C61—C51120.71 (14)
C26—C16—C15121.30 (15)N60—C62—C63122.88 (15)
C26—C16—H16119.3N60—C62—H62118.6
C15—C16—H16119.3C63—C62—H62118.6
N20—C21—C25123.77 (14)C64—C63—C62119.78 (16)
N20—C21—C11115.83 (13)C64—C63—H63120.1
C25—C21—C11120.40 (14)C62—C63—H63120.1
N20—C22—C23122.50 (15)C63—C64—C65119.43 (15)
N20—C22—H22118.8C63—C64—H64120.3
C23—C22—H22118.8C65—C64—H64120.3
C24—C23—C22119.98 (16)C64—C65—C61117.30 (15)
C24—C23—H23120.0C64—C65—C66124.76 (15)
C22—C23—H23120.0C61—C65—C66117.93 (15)
C23—C24—C25119.49 (15)C56—C66—C65121.35 (15)
C23—C24—H24120.3C56—C66—H66119.3
C25—C24—H24120.3C65—C66—H66119.3
C21—C25—C24116.93 (14)C4—C1—C2119.42 (16)
C21—C25—C26118.57 (15)C4—C1—C3120.67 (17)
C24—C25—C26124.50 (15)C2—C1—C3119.90 (17)
C16—C26—C25120.99 (15)N2—C2—C1179.2 (2)
C16—C26—H26119.5N3—C3—C1178.9 (2)
C25—C26—H26119.5N4—C4—C1177.6 (2)
N30—C31—C35123.54 (15)C6—C5—C8118.8 (9)
N30—C31—C41115.77 (14)C6—C5—C7119.6 (9)
C35—C31—C41120.69 (14)C8—C5—C7120.77 (18)
N30—C32—C33123.00 (16)C8—C5—C6A121.1 (9)
N30—C32—H32118.5C7—C5—C6A117.3 (9)
C33—C32—H32118.5N6—C6—C5175.1 (12)
C34—C33—C32119.99 (17)N6A—C6A—C5176.0 (10)
C34—C33—H33120.0N7—C7—C5179.9 (3)
C32—C33—H33120.0N8—C8—C5179.1 (2)
Tris(2,2'-bipyridine-κ2N,N')iron(II) bis(tricyanomethanide) sesquihydrate (II) top
Crystal data top
[Fe(C10H8N2)3](C4N3)2·1.5H2ODx = 1.299 Mg m3
Mr = 731.56Mo Kα radiation, λ = 0.71069 Å
Trigonal, R32:HCell parameters from 19620 reflections
a = 15.4137 (6) Åθ = 1.7–29.5°
c = 27.2718 (14) ŵ = 0.45 mm1
V = 5611.2 (5) Å3T = 193 K
Z = 6Prism, dark red
F(000) = 22620.20 × 0.11 × 0.11 mm
Data collection top
Stoe IPDSII
diffractometer
2420 reflections with I > 2σ(I)
ω scansRint = 0.029
Absorption correction: numerical
(XPREP in SHELXTL; Sheldrick, 2008)
θmax = 26.5°, θmin = 1.7°
Tmin = 0.854, Tmax = 0.914h = 1919
14192 measured reflectionsk = 1919
2592 independent reflectionsl = 3434
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.027H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.061 w = 1/[σ2(Fo2) + (0.0418P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
2592 reflectionsΔρmax = 0.26 e Å3
166 parametersΔρmin = 0.32 e Å3
0 restraintsAbsolute structure: Refined as an inversion twin; Flack (1983), with HOW MANY Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.48 (2)
Special details top

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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe11.00001.00000.80752 (2)0.03149 (13)
N100.98006 (13)0.88285 (13)0.84557 (6)0.0366 (4)
N200.88653 (13)0.89542 (13)0.76990 (6)0.0355 (4)
C110.9064 (2)0.79337 (15)0.82873 (8)0.0442 (5)
C121.03318 (19)0.8830 (2)0.88472 (8)0.0458 (5)
H121.08570.94520.89650.055*
C131.0142 (2)0.7958 (2)0.90847 (11)0.0601 (7)
H131.05180.79850.93660.072*
C140.9406 (3)0.7057 (2)0.89086 (14)0.0765 (10)
H140.92730.64500.90620.092*
C150.8858 (2)0.7040 (2)0.85052 (12)0.0690 (9)
H150.83440.64210.83780.083*
C210.85033 (17)0.80076 (17)0.78679 (9)0.0416 (5)
C220.83910 (16)0.90937 (19)0.73183 (7)0.0417 (5)
H220.86400.97530.71960.050*
C230.75557 (19)0.8314 (2)0.70987 (9)0.0495 (6)
H230.72420.84370.68290.059*
C240.7185 (2)0.7358 (2)0.72764 (10)0.0574 (7)
H240.66060.68140.71340.069*
C250.7665 (2)0.7197 (2)0.76646 (10)0.0554 (7)
H250.74240.65410.77900.066*
C10.66670.33330.95444 (14)0.0506 (9)
C20.7673 (2)0.4078 (2)0.95174 (10)0.0568 (7)
N20.8505 (2)0.4692 (2)0.94954 (13)0.0829 (8)
C30.66670.33330.83330.0385 (9)
C40.66670.4242 (2)0.83330.0456 (7)
N40.66670.4985 (2)0.83330.0698 (10)
C51.00001.00001.00000.0444 (11)
C60.9082 (3)0.9082 (3)1.00000.0485 (8)
N60.8337 (2)0.8337 (2)1.00000.0687 (10)
O11.00000.6426 (3)1.00000.1135 (17)
H10.950 (4)0.575 (4)0.9843 (18)0.136*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.03306 (16)0.03306 (16)0.0284 (2)0.01653 (8)0.0000.000
N100.0371 (9)0.0393 (10)0.0345 (9)0.0199 (8)0.0032 (8)0.0009 (8)
N200.0378 (9)0.0392 (10)0.0310 (9)0.0204 (8)0.0013 (7)0.0001 (8)
C110.0444 (14)0.0372 (10)0.0473 (11)0.0176 (11)0.0067 (11)0.0043 (8)
C120.0481 (13)0.0501 (13)0.0420 (12)0.0267 (11)0.0093 (10)0.0011 (10)
C130.0646 (17)0.0634 (17)0.0560 (15)0.0347 (14)0.0138 (13)0.0128 (13)
C140.081 (2)0.0515 (17)0.087 (2)0.0260 (16)0.0208 (19)0.0221 (16)
C150.0714 (19)0.0392 (13)0.081 (2)0.0164 (12)0.0248 (16)0.0110 (13)
C210.0400 (12)0.0385 (11)0.0428 (11)0.0168 (10)0.0052 (10)0.0014 (9)
C220.0435 (11)0.0456 (14)0.0347 (9)0.0214 (11)0.0041 (8)0.0017 (10)
C230.0488 (13)0.0612 (16)0.0375 (12)0.0266 (12)0.0108 (10)0.0032 (11)
C240.0498 (14)0.0532 (15)0.0549 (15)0.0150 (12)0.0183 (12)0.0093 (12)
C250.0545 (15)0.0407 (13)0.0565 (15)0.0130 (11)0.0130 (13)0.0007 (11)
C10.0579 (14)0.0579 (14)0.0361 (17)0.0289 (7)0.0000.000
C20.0639 (18)0.0589 (17)0.0489 (14)0.0317 (14)0.0049 (12)0.0053 (11)
N20.0629 (17)0.0726 (18)0.102 (2)0.0258 (16)0.0078 (15)0.0082 (16)
C30.0392 (14)0.0392 (14)0.037 (2)0.0196 (7)0.0000.000
C40.0376 (17)0.0439 (14)0.0531 (19)0.0188 (9)0.0054 (15)0.0027 (7)
N40.0541 (19)0.0455 (13)0.113 (3)0.0271 (10)0.012 (2)0.0061 (10)
C50.0459 (16)0.0459 (16)0.041 (2)0.0230 (8)0.0000.000
C60.0515 (16)0.0515 (16)0.0414 (18)0.0250 (19)0.0060 (8)0.0060 (8)
N60.0595 (15)0.0595 (15)0.070 (2)0.0172 (18)0.0113 (10)0.0113 (10)
O10.147 (4)0.0912 (18)0.121 (4)0.073 (2)0.072 (3)0.0362 (17)
Geometric parameters (Å, º) top
Fe1—N101.9689 (18)C22—C231.383 (3)
Fe1—N10i1.9690 (18)C22—H220.9500
Fe1—N10ii1.9690 (18)C23—C241.375 (4)
Fe1—N201.9725 (18)C23—H230.9500
Fe1—N20ii1.9725 (18)C24—C251.383 (4)
Fe1—N20i1.9725 (18)C24—H240.9500
N10—C121.345 (3)C25—H250.9500
N10—C111.355 (3)C1—C2iii1.396 (3)
N20—C221.348 (3)C1—C2iv1.396 (3)
N20—C211.356 (3)C1—C21.396 (3)
C11—C151.383 (3)C2—N21.154 (4)
C11—C211.472 (3)C3—C4iii1.400 (3)
C12—C131.384 (4)C3—C4iv1.400 (4)
C12—H120.9500C3—C41.400 (3)
C13—C141.367 (4)C4—N41.146 (5)
C13—H130.9500C5—C6ii1.415 (4)
C14—C151.379 (4)C5—C6i1.415 (4)
C14—H140.9500C5—C61.415 (4)
C15—H150.9500C6—N61.149 (5)
C21—C251.387 (4)O1—H11.02 (5)
N10—Fe1—N10i94.78 (7)C15—C14—H14120.4
N10—Fe1—N10ii94.78 (7)C14—C15—C11119.4 (3)
N10i—Fe1—N10ii94.78 (7)C14—C15—H15120.3
N10—Fe1—N2081.76 (7)C11—C15—H15120.3
N10i—Fe1—N20175.62 (8)N20—C21—C25122.0 (2)
N10ii—Fe1—N2088.21 (7)N20—C21—C11113.93 (19)
N10—Fe1—N20ii175.62 (8)C25—C21—C11124.0 (2)
N10i—Fe1—N20ii88.21 (7)N20—C22—C23122.6 (2)
N10ii—Fe1—N20ii81.76 (7)N20—C22—H22118.7
N20—Fe1—N20ii95.40 (7)C23—C22—H22118.7
N10—Fe1—N20i88.21 (7)C24—C23—C22119.1 (2)
N10i—Fe1—N20i81.76 (7)C24—C23—H23120.5
N10ii—Fe1—N20i175.62 (8)C22—C23—H23120.5
N20—Fe1—N20i95.40 (7)C23—C24—C25119.3 (2)
N20ii—Fe1—N20i95.40 (7)C23—C24—H24120.4
C12—N10—C11118.0 (2)C25—C24—H24120.4
C12—N10—Fe1126.97 (16)C24—C25—C21119.0 (2)
C11—N10—Fe1114.96 (14)C24—C25—H25120.5
C22—N20—C21118.0 (2)C21—C25—H25120.5
C22—N20—Fe1126.90 (16)C2iii—C1—C2iv119.72 (4)
C21—N20—Fe1114.99 (15)C2iii—C1—C2119.72 (4)
N10—C11—C15121.8 (2)C2iv—C1—C2119.72 (4)
N10—C11—C21114.21 (19)N2—C2—C1179.9 (4)
C15—C11—C21124.0 (2)C4iii—C3—C4iv120.004 (2)
N10—C12—C13122.5 (2)C4iii—C3—C4119.998 (4)
N10—C12—H12118.8C4iv—C3—C4119.997 (2)
C13—C12—H12118.8N4—C4—C3180.0
C14—C13—C12119.1 (3)C6ii—C5—C6i120.000 (7)
C14—C13—H13120.4C6ii—C5—C6120.000 (2)
C12—C13—H13120.4C6i—C5—C6120.000 (2)
C13—C14—C15119.2 (3)N6—C6—C5180.0 (6)
C13—C14—H14120.4
Symmetry codes: (i) y+2, xy+1, z; (ii) x+y+1, x+2, z; (iii) x+y+1, x+1, z; (iv) y+1, xy, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N21.02 (5)1.85 (5)2.861 (4)168 (4)
 

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