fac-Bis[bis­(pyridin-2-yl)methanamine]­iron(II) bis­(1,1,3,3-tetra­cyano-2-eth­oxy­propenide) dihydrate

The hydrated complex [Fe(DIPA)₂](tcnoet)₂·2H₂O [DIPA is bis­(pyridin-2-yl)methanamine, C₁₁H₁₁N₃, and tcnoet is the anion 1,1,3,3-tetra­cyano-2-eth­oxy­propenide, C₉H₅N₄O⁻], crystallizes with the [Fe(DIPA)₂]²⁺ cation located on an inversion centre. The coordination geometry for Fe^II is strongly distorted from octa­hedral, as a consequence of the bite angles formed by the tridentate DIPA ligand. The water mol­ecules included in the voids left by the cations and anions form hydrogen bonds with the cyano and amine groups.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.115
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.602 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          4 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         79 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Note

   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
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 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: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).

fac-Bis[bis(pyridin-2-yl)methanamine]iron(II) bis(1,1,3,3-tetracyano-2-ethoxypropenide) dihydrate

Crystal data

[Fe(C11H11N3)2](C9H5N4O)2·2H2O	F(000) = 864
Mr = 832.68	Dx = 1.391 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 11.8904 (3) Å	Cell parameters from 3092 reflections
b = 7.5824 (3) Å	θ = 4.9–71.4°
c = 22.5912 (7) Å	µ = 3.55 mm^−1
β = 102.648 (3)°	T = 173 K
V = 1987.35 (11) Å^3	Prism, red
Z = 2	0.12 × 0.08 × 0.07 mm

Data collection

Agilent Xcalibur diffractometer	3799 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3393 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.0416 pixels mm^-1	θmax = 71.5°, θmin = 3.8°
ω scans	h = −8→14
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −9→9
Tmin = 0.843, Tmax = 1.000	l = −27→26
8154 measured reflections

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)] = 0.045	Hydrogen site location: mixed
wR(F^2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 1.1004P] where P = (Fo^2 + 2Fc^2)/3
3799 reflections	(Δ/σ)max < 0.001
275 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3
0 constraints

Special details

Refinement. H atoms for the water molecule, H1 and H2, were found in a difference map and refined freely, while other H atoms were placed in calculated positions.

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

	x	y	z	Uiso*/Ueq
Fe1	0.500000	0.500000	0.500000	0.02633 (14)
N1	0.47707 (16)	0.5225 (2)	0.41019 (8)	0.0283 (4)
N2	0.58098 (16)	0.7306 (3)	0.49521 (8)	0.0303 (4)
H2B	0.530419	0.819642	0.481911	0.036*
H2C	0.627271	0.760881	0.531435	0.036*
N3	0.65696 (15)	0.4086 (3)	0.50006 (8)	0.0287 (4)
C1	0.3948 (2)	0.4541 (3)	0.36576 (11)	0.0349 (5)
H1A	0.334845	0.386283	0.376208	0.042*
C2	0.3951 (2)	0.4799 (4)	0.30524 (11)	0.0428 (6)
H2A	0.336248	0.429819	0.274536	0.051*
C3	0.4821 (2)	0.5793 (4)	0.28976 (11)	0.0448 (6)
H3A	0.484164	0.597059	0.248387	0.054*
C4	0.5656 (2)	0.6523 (4)	0.33527 (11)	0.0381 (5)
H4A	0.625319	0.722921	0.325822	0.046*
C5	0.56069 (18)	0.6207 (3)	0.39475 (10)	0.0300 (5)
C6	0.64886 (19)	0.6820 (3)	0.44945 (10)	0.0317 (5)
H6A	0.697765	0.781002	0.440069	0.038*
C7	0.71790 (19)	0.5212 (3)	0.47388 (10)	0.0305 (5)
C8	0.82888 (19)	0.4864 (3)	0.46739 (11)	0.0339 (5)
H8A	0.869537	0.569249	0.448410	0.041*
C9	0.8789 (2)	0.3285 (4)	0.48920 (11)	0.0374 (5)
H9A	0.955088	0.300655	0.485800	0.045*
C10	0.8163 (2)	0.2115 (4)	0.51606 (11)	0.0389 (5)
H10A	0.848966	0.101461	0.530923	0.047*
C11	0.7063 (2)	0.2551 (3)	0.52122 (10)	0.0344 (5)
H11A	0.664212	0.174451	0.540237	0.041*
C12	0.09125 (19)	0.7045 (3)	0.67459 (10)	0.0304 (5)
C13	0.21113 (19)	0.6807 (3)	0.69238 (10)	0.0337 (5)
C14	0.2614 (2)	0.5841 (4)	0.74535 (11)	0.0397 (6)
N15	0.3030 (2)	0.5080 (4)	0.78845 (11)	0.0539 (7)
C16	0.28834 (19)	0.7605 (3)	0.66036 (10)	0.0343 (5)
N17	0.35231 (17)	0.8214 (3)	0.63518 (10)	0.0431 (5)
C18	0.03496 (19)	0.8350 (3)	0.63568 (10)	0.0319 (5)
C19	−0.0856 (2)	0.8176 (3)	0.61052 (11)	0.0359 (5)
N20	−0.18179 (19)	0.8052 (3)	0.58885 (11)	0.0495 (6)
C21	0.0890 (2)	0.9891 (3)	0.61936 (13)	0.0406 (6)
N22	0.1294 (2)	1.1153 (4)	0.60585 (15)	0.0630 (8)
O23	0.01861 (14)	0.5995 (2)	0.69608 (8)	0.0359 (4)
C24	0.0371 (2)	0.4105 (4)	0.70181 (12)	0.0420 (6)
H24A	0.066260	0.377862	0.744869	0.050*
H24B	0.093996	0.372397	0.678350	0.050*
C25	−0.0772 (3)	0.3253 (4)	0.67742 (14)	0.0521 (7)
H25A	−0.069029	0.196912	0.681080	0.078*
H25B	−0.104317	0.357179	0.634632	0.078*
H25C	−0.132936	0.365979	0.700568	0.078*
O1	0.54085 (17)	0.9789 (3)	0.58946 (8)	0.0392 (4)
H1	0.591 (3)	0.990 (4)	0.6229 (18)	0.059*
H2	0.487 (3)	0.928 (5)	0.6009 (16)	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0235 (2)	0.0339 (3)	0.0221 (2)	−0.0020 (2)	0.00606 (17)	−0.0021 (2)
N1	0.0273 (9)	0.0310 (10)	0.0267 (9)	0.0039 (7)	0.0060 (7)	0.0008 (7)
N2	0.0303 (9)	0.0317 (10)	0.0284 (9)	−0.0034 (8)	0.0053 (7)	−0.0018 (8)
N3	0.0269 (8)	0.0354 (10)	0.0237 (8)	−0.0022 (8)	0.0051 (7)	−0.0026 (8)
C1	0.0321 (11)	0.0411 (13)	0.0302 (11)	0.0022 (10)	0.0040 (9)	−0.0021 (10)
C2	0.0405 (13)	0.0561 (17)	0.0284 (12)	0.0081 (12)	0.0005 (10)	−0.0026 (11)
C3	0.0489 (14)	0.0619 (18)	0.0246 (11)	0.0167 (13)	0.0101 (10)	0.0075 (11)
C4	0.0367 (12)	0.0447 (14)	0.0349 (12)	0.0072 (11)	0.0118 (10)	0.0113 (11)
C5	0.0308 (10)	0.0299 (11)	0.0305 (11)	0.0066 (9)	0.0096 (9)	0.0051 (9)
C6	0.0316 (10)	0.0313 (12)	0.0333 (11)	−0.0043 (9)	0.0098 (9)	0.0015 (9)
C7	0.0294 (11)	0.0352 (12)	0.0261 (10)	−0.0040 (9)	0.0041 (9)	0.0004 (9)
C8	0.0277 (11)	0.0425 (14)	0.0309 (11)	−0.0053 (10)	0.0050 (9)	−0.0002 (10)
C9	0.0280 (10)	0.0495 (15)	0.0331 (12)	0.0044 (10)	0.0035 (9)	−0.0044 (11)
C10	0.0408 (12)	0.0390 (13)	0.0334 (12)	0.0058 (11)	0.0004 (10)	0.0033 (10)
C11	0.0390 (12)	0.0353 (13)	0.0282 (10)	−0.0003 (10)	0.0058 (9)	0.0045 (10)
C12	0.0309 (10)	0.0350 (12)	0.0272 (10)	−0.0021 (9)	0.0101 (9)	−0.0021 (9)
C13	0.0310 (11)	0.0423 (14)	0.0287 (11)	0.0007 (10)	0.0085 (9)	0.0036 (10)
C14	0.0297 (11)	0.0538 (16)	0.0372 (13)	0.0040 (11)	0.0109 (10)	0.0052 (12)
N15	0.0409 (12)	0.0785 (19)	0.0416 (13)	0.0115 (12)	0.0074 (10)	0.0193 (13)
C16	0.0280 (10)	0.0444 (14)	0.0284 (11)	−0.0005 (10)	0.0013 (9)	−0.0008 (10)
N17	0.0291 (9)	0.0625 (15)	0.0378 (11)	−0.0054 (10)	0.0074 (9)	0.0055 (10)
C18	0.0286 (10)	0.0354 (13)	0.0329 (11)	−0.0019 (9)	0.0093 (9)	0.0031 (10)
C19	0.0368 (13)	0.0357 (13)	0.0354 (12)	0.0031 (10)	0.0084 (10)	0.0055 (10)
N20	0.0375 (12)	0.0540 (15)	0.0526 (13)	−0.0038 (10)	0.0006 (10)	0.0110 (12)
C21	0.0349 (12)	0.0391 (14)	0.0515 (15)	0.0061 (11)	0.0174 (11)	0.0070 (12)
N22	0.0562 (14)	0.0428 (14)	0.102 (2)	0.0016 (12)	0.0435 (15)	0.0168 (15)
O23	0.0346 (8)	0.0367 (9)	0.0398 (9)	0.0000 (7)	0.0156 (7)	0.0070 (7)
C24	0.0467 (14)	0.0387 (14)	0.0432 (14)	−0.0013 (11)	0.0156 (11)	0.0057 (11)
C25	0.0606 (17)	0.0489 (17)	0.0465 (15)	−0.0134 (14)	0.0112 (13)	−0.0009 (13)
O1	0.0429 (10)	0.0412 (10)	0.0338 (9)	−0.0055 (8)	0.0094 (8)	0.0029 (8)

Geometric parameters (Å, º)

Fe1—N3^i	1.9904 (18)	C8—H8A	0.9500
Fe1—N3	1.9904 (18)	C9—C10	1.380 (4)
Fe1—N1^i	1.9944 (18)	C9—H9A	0.9500
Fe1—N1	1.9944 (18)	C10—C11	1.379 (3)
Fe1—N2^i	2.0106 (19)	C10—H10A	0.9500
Fe1—N2	2.0106 (19)	C11—H11A	0.9500
N1—C1	1.343 (3)	C12—O23	1.341 (3)
N1—C5	1.348 (3)	C12—C18	1.393 (3)
N2—C6	1.490 (3)	C12—C13	1.405 (3)
N2—H2B	0.9100	C13—C14	1.418 (3)
N2—H2C	0.9100	C13—C16	1.423 (3)
N3—C7	1.338 (3)	C14—N15	1.147 (3)
N3—C11	1.343 (3)	C16—N17	1.142 (3)
C1—C2	1.382 (3)	C18—C21	1.420 (3)
C1—H1A	0.9500	C18—C19	1.428 (3)
C2—C3	1.385 (4)	C19—N20	1.145 (3)
C2—H2A	0.9500	C21—N22	1.142 (4)
C3—C4	1.379 (4)	O23—C24	1.451 (3)
C3—H3A	0.9500	C24—C25	1.496 (4)
C4—C5	1.379 (3)	C24—H24A	0.9900
C4—H4A	0.9500	C24—H24B	0.9900
C5—C6	1.508 (3)	C25—H25A	0.9800
C6—C7	1.506 (3)	C25—H25B	0.9800
C6—H6A	1.0000	C25—H25C	0.9800
C7—C8	1.385 (3)	O1—H1	0.86 (4)
C8—C9	1.379 (4)	O1—H2	0.84 (4)
N3^i—Fe1—N3	180.0	N2—C6—H6A	112.9
N3^i—Fe1—N1^i	87.13 (7)	C7—C6—H6A	112.9
N3—Fe1—N1^i	92.87 (7)	C5—C6—H6A	112.9
N3^i—Fe1—N1	92.88 (7)	N3—C7—C8	123.1 (2)
N3—Fe1—N1	87.13 (7)	N3—C7—C6	111.96 (19)
N1^i—Fe1—N1	180.0	C8—C7—C6	124.8 (2)
N3^i—Fe1—N2^i	80.95 (8)	C9—C8—C7	118.3 (2)
N3—Fe1—N2^i	99.05 (8)	C9—C8—H8A	120.9
N1^i—Fe1—N2^i	80.28 (8)	C7—C8—H8A	120.9
N1—Fe1—N2^i	99.72 (8)	C8—C9—C10	118.9 (2)
N3^i—Fe1—N2	99.05 (8)	C8—C9—H9A	120.5
N3—Fe1—N2	80.95 (8)	C10—C9—H9A	120.5
N1^i—Fe1—N2	99.72 (8)	C11—C10—C9	119.7 (2)
N1—Fe1—N2	80.27 (8)	C11—C10—H10A	120.1
N2^i—Fe1—N2	180.0	C9—C10—H10A	120.1
C1—N1—C5	118.5 (2)	N3—C11—C10	121.7 (2)
C1—N1—Fe1	129.96 (16)	N3—C11—H11A	119.1
C5—N1—Fe1	111.50 (15)	C10—C11—H11A	119.1
C6—N2—Fe1	99.26 (13)	O23—C12—C18	113.05 (19)
C6—N2—H2B	111.9	O23—C12—C13	120.9 (2)
Fe1—N2—H2B	111.9	C18—C12—C13	126.1 (2)
C6—N2—H2C	111.9	C12—C13—C14	121.4 (2)
Fe1—N2—H2C	111.9	C12—C13—C16	121.8 (2)
H2B—N2—H2C	109.6	C14—C13—C16	116.7 (2)
C7—N3—C11	118.26 (19)	N15—C14—C13	179.0 (3)
C7—N3—Fe1	112.10 (16)	N17—C16—C13	178.3 (3)
C11—N3—Fe1	129.63 (16)	C12—C18—C21	124.5 (2)
N1—C1—C2	121.7 (2)	C12—C18—C19	119.2 (2)
N1—C1—H1A	119.1	C21—C18—C19	116.4 (2)
C2—C1—H1A	119.1	N20—C19—C18	178.1 (3)
C1—C2—C3	119.4 (2)	N22—C21—C18	178.0 (3)
C1—C2—H2A	120.3	C12—O23—C24	121.45 (18)
C3—C2—H2A	120.3	O23—C24—C25	106.6 (2)
C4—C3—C2	119.1 (2)	O23—C24—H24A	110.4
C4—C3—H3A	120.5	C25—C24—H24A	110.4
C2—C3—H3A	120.5	O23—C24—H24B	110.4
C5—C4—C3	118.6 (2)	C25—C24—H24B	110.4
C5—C4—H4A	120.7	H24A—C24—H24B	108.6
C3—C4—H4A	120.7	C24—C25—H25A	109.5
N1—C5—C4	122.7 (2)	C24—C25—H25B	109.5
N1—C5—C6	112.21 (19)	H25A—C25—H25B	109.5
C4—C5—C6	125.1 (2)	C24—C25—H25C	109.5
N2—C6—C7	106.29 (18)	H25A—C25—H25C	109.5
N2—C6—C5	105.05 (17)	H25B—C25—H25C	109.5
C7—C6—C5	106.01 (19)	H1—O1—H2	102 (3)
C5—N1—C1—C2	1.0 (3)	C5—C6—C7—N3	−71.4 (2)
Fe1—N1—C1—C2	−177.85 (19)	N2—C6—C7—C8	−143.5 (2)
N1—C1—C2—C3	−0.3 (4)	C5—C6—C7—C8	105.0 (2)
C1—C2—C3—C4	−0.8 (4)	N3—C7—C8—C9	−0.2 (4)
C2—C3—C4—C5	1.2 (4)	C6—C7—C8—C9	−176.3 (2)
C1—N1—C5—C4	−0.6 (3)	C7—C8—C9—C10	0.5 (3)
Fe1—N1—C5—C4	178.47 (18)	C8—C9—C10—C11	−0.7 (4)
C1—N1—C5—C6	−177.8 (2)	C7—N3—C11—C10	−0.5 (3)
Fe1—N1—C5—C6	1.2 (2)	Fe1—N3—C11—C10	178.39 (17)
C3—C4—C5—N1	−0.5 (4)	C9—C10—C11—N3	0.8 (4)
C3—C4—C5—C6	176.3 (2)	O23—C12—C13—C14	−18.8 (4)
Fe1—N2—C6—C7	−55.23 (17)	C18—C12—C13—C14	159.7 (3)
Fe1—N2—C6—C5	56.87 (17)	O23—C12—C13—C16	165.0 (2)
N1—C5—C6—N2	−40.1 (2)	C18—C12—C13—C16	−16.5 (4)
C4—C5—C6—N2	142.7 (2)	O23—C12—C18—C21	162.7 (2)
N1—C5—C6—C7	72.2 (2)	C13—C12—C18—C21	−15.9 (4)
C4—C5—C6—C7	−105.0 (3)	O23—C12—C18—C19	−16.3 (3)
C11—N3—C7—C8	0.3 (3)	C13—C12—C18—C19	165.1 (2)
Fe1—N3—C7—C8	−178.85 (18)	C18—C12—O23—C24	139.3 (2)
C11—N3—C7—C6	176.80 (19)	C13—C12—O23—C24	−42.0 (3)
Fe1—N3—C7—C6	−2.3 (2)	C12—O23—C24—C25	−135.0 (2)
N2—C6—C7—N3	40.0 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N15^ii	0.86 (4)	2.12 (4)	2.976 (3)	172 (3)
O1—H2···N17	0.84 (4)	2.09 (4)	2.921 (3)	175 (4)
N2—H2B···O1^iii	0.91	2.25	3.065 (3)	149
N2—H2C···N20^iv	0.91	2.38	3.184 (3)	148
N2—H2C···O1	0.91	2.47	2.958 (3)	114

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