Tris(1,10-phenanthroline-κ(2) N,N')iron(II) bis-(1,1,3,3-tetra-cyano-2-eth-oxy-propenide) hemihydrate.

In the title hydrated mol-ecular salt, [Fe(C12H8N2)3](C9H5N4O)2·0.5H2O, the water mol-ecule site is half-occupied. The Fe-N bond lengths within the octa-hedral tris-chelate [Fe(phen)3](2+) ion (phen is 1,10-phenantroline) are indicative of a low-spin d(6) electronic configuration for the metal ion. The C-N, C-C and C-O bond lengths in the polynitrile anions indicate extensive electronic delocalization. In the crystal, the components are linked through O-H⋯N hydrogen bonds, forming [100] chains, as well as through Coulombic inter-actions.

Related literature

For background to 1,10-phenanthroline as a chelating ligand, see: Hoshina et al. (2000 ▶); Hwang & Ha (2006 ▶); Aparici Plaza et al. (2007 ▶); Zhou & Guo (2007 ▶). For a related structure, see: Cai & Zhan (2012 ▶). For further synthetic details, see: Middleton & Engelhardt (1958 ▶).

Experimental

Crystal data

[Fe(C12H8N2)3](C9H5N4O)2·0.5H2O

M = 975.81

Triclinic,

a = 9.3497 (3) Å

b = 14.1736 (4) Å

c = 18.6086 (6) Å

α = 94.462 (2)°

β = 96.562 (1)°

γ = 101.129 (1)°

V = 2391.12 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 293 K

0.55 × 0.35 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.820, T max = 0.946

38167 measured reflections

10845 independent reflections

6909 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.134

S = 1.02

10845 reflections

661 parameters

40 restraints

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048611/hb6994sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048611/hb6994Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(C12H8N2)3](C9H5N4O)2·0.5H2O	Z = 2
Mr = 975.81	F(000) = 1006
Triclinic, P1	Dx = 1.355 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3497 (3) Å	Cell parameters from 7674 reflections
b = 14.1736 (4) Å	θ = 2.6–23.7°
c = 18.6086 (6) Å	µ = 0.38 mm−1
α = 94.462 (2)°	T = 293 K
β = 96.562 (1)°	Prism, red
γ = 101.129 (1)°	0.55 × 0.35 × 0.15 mm
V = 2391.12 (13) Å3

Bruker SMART APEX CCD diffractometer	10845 independent reflections
Radiation source: fine-focus sealed tube	6909 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→9
Tmin = 0.820, Tmax = 0.946	k = −18→18
38167 measured reflections	l = −23→24

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0594P)2 + 0.6022P] where P = (Fo2 + 2Fc2)/3
10845 reflections	(Δ/σ)max = 0.001
661 parameters	Δρmax = 0.36 e Å−3
40 restraints	Δρmin = −0.43 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.50347 (3)	0.85774 (2)	0.224833 (17)	0.03344 (11)
O1	0.3012 (2)	0.22872 (14)	0.20343 (10)	0.0616 (5)
O2	1.14419 (19)	0.66090 (12)	0.39687 (10)	0.0537 (5)
O1W	0.7463 (5)	0.5451 (3)	0.1682 (3)	0.0894 (15)	0.50
H11	0.6566	0.5202	0.1662	0.134*	0.50
H12	0.7908	0.5022	0.1546	0.134*	0.50
N1	0.5443 (2)	0.76256 (13)	0.29244 (10)	0.0361 (4)
N2	0.39483 (19)	0.89919 (13)	0.30300 (10)	0.0376 (4)
N3	0.4689 (2)	0.95925 (14)	0.16118 (10)	0.0380 (4)
N4	0.67007 (19)	0.95977 (14)	0.27045 (10)	0.0368 (4)
N5	0.6138 (2)	0.80877 (13)	0.15141 (10)	0.0367 (4)
N6	0.3394 (2)	0.76187 (13)	0.17130 (10)	0.0370 (4)
N7	0.4217 (3)	0.4827 (2)	0.16948 (15)	0.0812 (8)
N8	−0.0519 (3)	0.4093 (2)	0.12339 (18)	0.0859 (9)
N9	−0.1061 (3)	0.1837 (2)	0.02106 (15)	0.0761 (8)
N10	0.0661 (3)	0.0069 (2)	0.17246 (17)	0.0878 (9)
N11	0.9634 (3)	0.7897 (2)	0.28465 (15)	0.0779 (8)
N12	0.8732 (3)	0.87480 (19)	0.49783 (14)	0.0709 (7)
N13	0.8445 (4)	0.6721 (2)	0.58681 (16)	0.0889 (9)
N14	1.2477 (4)	0.5698 (2)	0.57159 (18)	0.0987 (10)
C1	0.4990 (2)	0.77928 (17)	0.35844 (12)	0.0394 (5)
C2	0.6104 (3)	0.68844 (17)	0.28387 (14)	0.0456 (6)
H2	0.6416	0.6750	0.2392	0.055*
C3	0.6353 (3)	0.6299 (2)	0.33882 (16)	0.0576 (7)
H3	0.6793	0.5774	0.3298	0.069*
C4	0.5956 (3)	0.6491 (2)	0.40522 (16)	0.0592 (8)
H4	0.6148	0.6115	0.4425	0.071*
C5	0.5254 (3)	0.72648 (19)	0.41700 (13)	0.0495 (6)
C6	0.4788 (3)	0.7556 (2)	0.48418 (15)	0.0650 (8)
H6	0.4979	0.7226	0.5243	0.078*
C7	0.4086 (3)	0.8287 (2)	0.49128 (14)	0.0643 (8)
H7	0.3815	0.8459	0.5363	0.077*
C8	0.3742 (3)	0.88111 (19)	0.43108 (14)	0.0499 (6)
C9	0.2964 (3)	0.9560 (2)	0.43273 (16)	0.0605 (8)
H9	0.2642	0.9766	0.4756	0.073*
C10	0.2684 (3)	0.9981 (2)	0.37134 (17)	0.0613 (8)
H10	0.2157	1.0474	0.3721	0.074*
C11	0.3178 (3)	0.96841 (18)	0.30664 (15)	0.0489 (6)
H11A	0.2960	0.9981	0.2651	0.059*
C12	0.4207 (2)	0.85541 (17)	0.36471 (12)	0.0383 (5)
C13	0.5731 (3)	1.04231 (17)	0.17762 (13)	0.0410 (6)
C14	0.3676 (3)	0.9556 (2)	0.10430 (13)	0.0486 (6)
H14	0.2952	0.8998	0.0924	0.058*
C15	0.3654 (4)	1.0324 (2)	0.06164 (16)	0.0637 (8)
H15	0.2933	1.0268	0.0219	0.076*
C16	0.4689 (4)	1.1150 (2)	0.07842 (17)	0.0659 (8)
H16	0.4680	1.1662	0.0501	0.079*
C17	0.5771 (3)	1.1230 (2)	0.13850 (15)	0.0546 (7)
C18	0.6900 (4)	1.2064 (2)	0.1631 (2)	0.0712 (9)
H18	0.6951	1.2606	0.1377	0.085*
C19	0.7891 (4)	1.2086 (2)	0.2221 (2)	0.0703 (9)
H19	0.8596	1.2646	0.2372	0.084*
C20	0.7877 (3)	1.12635 (19)	0.26187 (16)	0.0524 (7)
C21	0.8876 (3)	1.1224 (2)	0.32361 (17)	0.0632 (8)
H21	0.9611	1.1758	0.3415	0.076*
C22	0.8755 (3)	1.0399 (2)	0.35668 (16)	0.0596 (7)
H22	0.9398	1.0368	0.3980	0.071*
C23	0.7672 (3)	0.96011 (19)	0.32887 (14)	0.0464 (6)
H23	0.7619	0.9040	0.3521	0.056*
C24	0.6805 (3)	1.04381 (17)	0.23827 (13)	0.0407 (6)
C25	0.5282 (3)	0.73853 (16)	0.10219 (12)	0.0371 (5)
C26	0.7553 (3)	0.83529 (19)	0.14283 (13)	0.0456 (6)
H26	0.8160	0.8828	0.1760	0.055*
C27	0.8151 (3)	0.7944 (2)	0.08606 (15)	0.0561 (7)
H27	0.9139	0.8154	0.0815	0.067*
C28	0.7299 (3)	0.7238 (2)	0.03722 (15)	0.0583 (8)
H28	0.7702	0.6962	−0.0006	0.070*
C29	0.5804 (3)	0.69269 (18)	0.04414 (13)	0.0463 (6)
C30	0.4781 (4)	0.6204 (2)	−0.00332 (15)	0.0624 (8)
H30	0.5106	0.5886	−0.0420	0.075*
C31	0.3358 (4)	0.5970 (2)	0.00644 (15)	0.0609 (8)
H31	0.2720	0.5501	−0.0260	0.073*
C32	0.2801 (3)	0.64234 (17)	0.06550 (13)	0.0464 (6)
C33	0.1346 (3)	0.6214 (2)	0.08017 (16)	0.0574 (7)
H33	0.0648	0.5752	0.0499	0.069*
C34	0.0957 (3)	0.6688 (2)	0.13894 (16)	0.0561 (7)
H34	−0.0005	0.6542	0.1494	0.067*
C35	0.1998 (3)	0.73890 (19)	0.18332 (14)	0.0478 (6)
H35	0.1709	0.7710	0.2229	0.057*
C36	0.3778 (3)	0.71246 (16)	0.11279 (12)	0.0368 (5)
C37	0.4801 (14)	0.2478 (16)	0.3099 (11)	0.082 (3)	0.50
H37A	0.5131	0.2828	0.3570	0.123*	0.50
H37B	0.5590	0.2565	0.2807	0.123*	0.50
H37C	0.4493	0.1803	0.3150	0.123*	0.50
C38	0.3543 (10)	0.2847 (10)	0.2741 (5)	0.072 (2)	0.50
H38A	0.2758	0.2787	0.3044	0.086*	0.50
H38B	0.3854	0.3525	0.2675	0.086*	0.50
C37'	0.4354 (15)	0.2331 (16)	0.3176 (11)	0.082 (3)	0.50
H37D	0.5006	0.2716	0.3574	0.123*	0.50
H37E	0.4803	0.1826	0.2989	0.123*	0.50
H37F	0.3448	0.2052	0.3343	0.123*	0.50
C38'	0.4052 (10)	0.2956 (9)	0.2589 (5)	0.072 (2)	0.50
H38C	0.3616	0.3481	0.2767	0.086*	0.50
H38D	0.4946	0.3223	0.2395	0.086*	0.50
C39	0.3170 (3)	0.4245 (2)	0.16383 (15)	0.0592 (7)
C40	0.1870 (3)	0.3516 (2)	0.15409 (14)	0.0501 (6)
C41	0.0544 (3)	0.3820 (2)	0.13560 (16)	0.0588 (7)
C42	0.1886 (3)	0.2547 (2)	0.16271 (13)	0.0504 (7)
C43	0.0813 (3)	0.1764 (2)	0.13052 (14)	0.0511 (6)
C44	−0.0228 (3)	0.1823 (2)	0.07024 (16)	0.0550 (7)
C45	0.0744 (3)	0.0832 (2)	0.15443 (16)	0.0607 (8)
C46	1.2014 (13)	0.5419 (14)	0.3149 (9)	0.095 (3)	0.50
H46A	1.2218	0.4780	0.3106	0.143*	0.50
H46B	1.2914	0.5886	0.3169	0.143*	0.50
H46C	1.1344	0.5492	0.2737	0.143*	0.50
C47	1.1335 (19)	0.5573 (5)	0.3836 (10)	0.069 (2)	0.50
H47A	1.0315	0.5236	0.3773	0.082*	0.50
H47B	1.1864	0.5336	0.4240	0.082*	0.50
C46'	1.1337 (13)	0.5284 (14)	0.3094 (9)	0.095 (3)	0.50
H46D	1.1242	0.4595	0.3026	0.143*	0.50
H46E	1.2107	0.5588	0.2838	0.143*	0.50
H46F	1.0426	0.5450	0.2909	0.143*	0.50
C47'	1.1709 (19)	0.5630 (5)	0.3900 (10)	0.069 (2)	0.50
H47C	1.1089	0.5218	0.4182	0.082*	0.50
H47D	1.2730	0.5627	0.4068	0.082*	0.50
C48	1.0607 (3)	0.69078 (17)	0.44425 (14)	0.0446 (6)
C49	0.9870 (3)	0.76048 (18)	0.41913 (14)	0.0452 (6)
C50	0.9760 (3)	0.7760 (2)	0.34445 (17)	0.0527 (7)
C51	0.9244 (3)	0.8222 (2)	0.46418 (14)	0.0501 (6)
C52	1.0539 (3)	0.65510 (19)	0.51216 (15)	0.0523 (7)
C53	0.9382 (4)	0.6662 (2)	0.55343 (16)	0.0626 (8)
C54	1.1624 (4)	0.6080 (2)	0.54415 (17)	0.0662 (8)

	U11	U22	U33	U12	U13	U23
Fe1	0.03130 (18)	0.0387 (2)	0.0314 (2)	0.00944 (14)	0.00527 (13)	0.00311 (14)
O1	0.0539 (11)	0.0735 (13)	0.0546 (12)	0.0231 (10)	−0.0069 (9)	−0.0160 (10)
O2	0.0536 (11)	0.0461 (11)	0.0661 (12)	0.0149 (9)	0.0178 (9)	0.0074 (9)
O1W	0.056 (2)	0.070 (3)	0.133 (4)	−0.001 (2)	0.027 (3)	−0.035 (3)
N1	0.0345 (10)	0.0384 (11)	0.0353 (11)	0.0076 (8)	0.0043 (8)	0.0028 (8)
N2	0.0326 (10)	0.0412 (11)	0.0382 (11)	0.0067 (8)	0.0059 (8)	0.0001 (9)
N3	0.0371 (10)	0.0451 (12)	0.0351 (11)	0.0146 (9)	0.0069 (9)	0.0054 (9)
N4	0.0328 (10)	0.0419 (11)	0.0369 (11)	0.0109 (8)	0.0061 (8)	0.0013 (9)
N5	0.0367 (10)	0.0427 (11)	0.0335 (11)	0.0122 (9)	0.0070 (9)	0.0077 (9)
N6	0.0378 (10)	0.0401 (11)	0.0335 (11)	0.0088 (9)	0.0052 (8)	0.0040 (9)
N7	0.0645 (18)	0.086 (2)	0.083 (2)	−0.0033 (16)	0.0072 (15)	−0.0035 (16)
N8	0.0693 (18)	0.0659 (18)	0.118 (2)	0.0124 (15)	−0.0099 (17)	0.0170 (16)
N9	0.0671 (17)	0.092 (2)	0.0589 (17)	0.0024 (15)	−0.0104 (14)	0.0039 (15)
N10	0.0750 (19)	0.076 (2)	0.109 (2)	0.0100 (16)	−0.0034 (17)	0.0215 (18)
N11	0.0790 (19)	0.111 (2)	0.0620 (18)	0.0474 (17)	0.0268 (15)	0.0255 (16)
N12	0.0793 (18)	0.0732 (18)	0.0631 (17)	0.0322 (15)	0.0048 (14)	−0.0110 (13)
N13	0.115 (3)	0.0733 (19)	0.086 (2)	0.0148 (17)	0.054 (2)	0.0074 (16)
N14	0.090 (2)	0.100 (2)	0.106 (2)	0.0214 (19)	−0.0108 (19)	0.042 (2)
C1	0.0386 (13)	0.0425 (14)	0.0332 (13)	−0.0002 (10)	0.0031 (10)	0.0027 (11)
C2	0.0463 (14)	0.0454 (15)	0.0472 (15)	0.0145 (12)	0.0049 (12)	0.0066 (12)
C3	0.0578 (17)	0.0507 (17)	0.067 (2)	0.0177 (13)	0.0038 (15)	0.0157 (14)
C4	0.0579 (17)	0.0590 (18)	0.0603 (19)	0.0076 (14)	−0.0012 (15)	0.0277 (15)
C5	0.0507 (15)	0.0564 (17)	0.0364 (15)	−0.0006 (13)	0.0002 (12)	0.0098 (12)
C6	0.068 (2)	0.081 (2)	0.0409 (17)	−0.0001 (17)	0.0043 (14)	0.0167 (15)
C7	0.073 (2)	0.082 (2)	0.0306 (15)	−0.0034 (17)	0.0154 (14)	0.0008 (14)
C8	0.0446 (14)	0.0558 (17)	0.0433 (15)	−0.0037 (12)	0.0127 (12)	−0.0078 (13)
C9	0.0578 (17)	0.069 (2)	0.0530 (18)	0.0037 (15)	0.0260 (14)	−0.0111 (15)
C10	0.0505 (16)	0.0605 (18)	0.076 (2)	0.0179 (14)	0.0230 (15)	−0.0115 (16)
C11	0.0425 (14)	0.0524 (16)	0.0554 (17)	0.0181 (12)	0.0105 (12)	0.0007 (13)
C12	0.0349 (12)	0.0448 (14)	0.0315 (13)	0.0001 (10)	0.0070 (10)	−0.0028 (10)
C13	0.0434 (13)	0.0407 (14)	0.0436 (14)	0.0130 (11)	0.0162 (11)	0.0074 (11)
C14	0.0487 (15)	0.0585 (17)	0.0403 (14)	0.0169 (13)	0.0009 (12)	0.0072 (12)
C15	0.072 (2)	0.079 (2)	0.0474 (17)	0.0319 (18)	0.0023 (15)	0.0184 (16)
C16	0.085 (2)	0.064 (2)	0.063 (2)	0.0322 (18)	0.0232 (17)	0.0317 (16)
C17	0.0641 (18)	0.0508 (17)	0.0581 (18)	0.0190 (14)	0.0254 (15)	0.0180 (14)
C18	0.081 (2)	0.0509 (19)	0.089 (3)	0.0115 (17)	0.035 (2)	0.0229 (17)
C19	0.067 (2)	0.0474 (18)	0.093 (3)	−0.0028 (15)	0.0266 (19)	−0.0027 (17)
C20	0.0481 (15)	0.0428 (16)	0.0644 (19)	0.0014 (12)	0.0178 (14)	−0.0023 (13)
C21	0.0471 (16)	0.0581 (19)	0.072 (2)	−0.0079 (14)	0.0056 (15)	−0.0180 (16)
C22	0.0418 (15)	0.073 (2)	0.0561 (18)	0.0065 (14)	−0.0024 (13)	−0.0122 (16)
C23	0.0372 (13)	0.0557 (16)	0.0447 (15)	0.0100 (12)	0.0016 (11)	0.0001 (12)
C24	0.0379 (13)	0.0397 (14)	0.0457 (15)	0.0088 (11)	0.0118 (11)	0.0000 (11)
C25	0.0473 (14)	0.0394 (13)	0.0286 (12)	0.0175 (11)	0.0043 (10)	0.0068 (10)
C26	0.0384 (13)	0.0591 (16)	0.0427 (15)	0.0139 (12)	0.0103 (11)	0.0083 (12)
C27	0.0499 (16)	0.078 (2)	0.0499 (17)	0.0255 (15)	0.0206 (14)	0.0153 (16)
C28	0.072 (2)	0.077 (2)	0.0416 (16)	0.0423 (17)	0.0249 (15)	0.0109 (15)
C29	0.0640 (17)	0.0507 (16)	0.0308 (13)	0.0268 (13)	0.0072 (12)	0.0060 (12)
C30	0.091 (2)	0.0595 (19)	0.0419 (16)	0.0319 (17)	0.0086 (16)	−0.0019 (14)
C31	0.085 (2)	0.0477 (17)	0.0438 (17)	0.0128 (15)	−0.0054 (15)	−0.0096 (13)
C32	0.0587 (16)	0.0385 (14)	0.0396 (15)	0.0099 (12)	−0.0043 (12)	0.0050 (12)
C33	0.0582 (18)	0.0459 (16)	0.0581 (19)	−0.0028 (13)	−0.0112 (14)	0.0044 (14)
C34	0.0400 (14)	0.0572 (18)	0.0651 (19)	−0.0030 (13)	0.0010 (13)	0.0110 (15)
C35	0.0374 (13)	0.0552 (16)	0.0497 (16)	0.0047 (12)	0.0085 (12)	0.0064 (13)
C36	0.0452 (13)	0.0351 (13)	0.0310 (13)	0.0117 (11)	0.0002 (10)	0.0067 (10)
C37	0.069 (7)	0.107 (6)	0.065 (4)	0.019 (6)	−0.006 (5)	−0.002 (3)
C38	0.085 (6)	0.089 (4)	0.046 (4)	0.040 (4)	−0.001 (3)	−0.012 (3)
C37'	0.069 (7)	0.107 (6)	0.065 (4)	0.019 (6)	−0.006 (5)	−0.002 (3)
C38'	0.085 (6)	0.089 (4)	0.046 (4)	0.040 (4)	−0.001 (3)	−0.012 (3)
C39	0.0559 (18)	0.070 (2)	0.0483 (17)	0.0075 (16)	0.0082 (14)	−0.0055 (14)
C40	0.0497 (15)	0.0563 (17)	0.0422 (15)	0.0085 (13)	0.0055 (12)	−0.0003 (13)
C41	0.0578 (18)	0.0516 (17)	0.0642 (19)	0.0052 (14)	0.0025 (15)	0.0112 (14)
C42	0.0437 (14)	0.0711 (19)	0.0377 (15)	0.0164 (14)	0.0074 (12)	−0.0015 (13)
C43	0.0476 (15)	0.0593 (18)	0.0468 (16)	0.0133 (13)	0.0048 (12)	0.0044 (13)
C44	0.0518 (16)	0.0635 (18)	0.0467 (17)	0.0045 (14)	0.0077 (14)	0.0029 (14)
C45	0.0505 (17)	0.072 (2)	0.0584 (19)	0.0134 (15)	0.0040 (14)	0.0028 (16)
C46	0.132 (9)	0.079 (5)	0.080 (3)	0.027 (7)	0.032 (7)	−0.003 (3)
C47	0.076 (7)	0.0497 (19)	0.088 (4)	0.022 (3)	0.029 (4)	0.0052 (19)
C46'	0.132 (9)	0.079 (5)	0.080 (3)	0.027 (7)	0.032 (7)	−0.003 (3)
C47'	0.076 (7)	0.0497 (19)	0.088 (4)	0.022 (3)	0.029 (4)	0.0052 (19)
C48	0.0407 (13)	0.0393 (14)	0.0518 (16)	0.0043 (11)	0.0081 (12)	−0.0003 (12)
C49	0.0419 (14)	0.0455 (15)	0.0476 (16)	0.0081 (11)	0.0085 (12)	−0.0007 (12)
C50	0.0445 (15)	0.0611 (18)	0.0580 (19)	0.0185 (13)	0.0149 (13)	0.0085 (15)
C51	0.0466 (15)	0.0532 (17)	0.0488 (16)	0.0120 (13)	−0.0002 (13)	0.0002 (13)
C52	0.0560 (16)	0.0477 (16)	0.0509 (17)	0.0064 (13)	0.0051 (13)	0.0030 (13)
C53	0.085 (2)	0.0438 (17)	0.0564 (19)	0.0035 (15)	0.0148 (17)	0.0034 (14)
C54	0.069 (2)	0.0602 (19)	0.066 (2)	0.0021 (16)	0.0033 (16)	0.0191 (16)

Fe1—N6	1.9563 (19)	C19—C20	1.426 (4)
Fe1—N5	1.9654 (18)	C19—H19	0.9300
Fe1—N4	1.9686 (19)	C20—C24	1.390 (3)
Fe1—N1	1.9752 (18)	C20—C21	1.407 (4)
Fe1—N2	1.9819 (18)	C21—C22	1.355 (4)
Fe1—N3	1.9836 (18)	C21—H21	0.9300
O1—C42	1.353 (3)	C22—C23	1.385 (4)
O1—C38	1.463 (6)	C22—H22	0.9300
O1—C38'	1.473 (6)	C23—H23	0.9300
O2—C48	1.339 (3)	C25—C29	1.401 (3)
O2—C47	1.452 (6)	C25—C36	1.424 (3)
O2—C47'	1.455 (6)	C26—C27	1.389 (3)
O1W—H11	0.8400	C26—H26	0.9300
O1W—H12	0.8400	C27—C28	1.359 (4)
N1—C2	1.326 (3)	C27—H27	0.9300
N1—C1	1.362 (3)	C28—C29	1.405 (4)
N2—C11	1.326 (3)	C28—H28	0.9300
N2—C12	1.367 (3)	C29—C30	1.426 (4)
N3—C14	1.328 (3)	C30—C31	1.344 (4)
N3—C13	1.364 (3)	C30—H30	0.9300
N4—C23	1.334 (3)	C31—C32	1.429 (4)
N4—C24	1.366 (3)	C31—H31	0.9300
N5—C26	1.336 (3)	C32—C36	1.388 (3)
N5—C25	1.361 (3)	C32—C33	1.398 (4)
N6—C35	1.332 (3)	C33—C34	1.360 (4)
N6—C36	1.368 (3)	C33—H33	0.9300
N7—C39	1.140 (4)	C34—C35	1.390 (4)
N8—C41	1.140 (4)	C34—H34	0.9300
N9—C44	1.136 (3)	C35—H35	0.9300
N10—C45	1.149 (4)	C37—C38	1.487 (9)
N11—C50	1.141 (3)	C37—H37A	0.9600
N12—C51	1.145 (3)	C37—H37B	0.9600
N13—C53	1.142 (4)	C37—H37C	0.9600
N14—C54	1.143 (4)	C38—H38A	0.9700
C1—C5	1.395 (3)	C38—H38B	0.9700
C1—C12	1.421 (3)	C37'—C38'	1.495 (9)
C2—C3	1.393 (3)	C37'—H37D	0.9600
C2—H2	0.9300	C37'—H37E	0.9600
C3—C4	1.353 (4)	C37'—H37F	0.9600
C3—H3	0.9300	C38'—H38C	0.9700
C4—C5	1.398 (4)	C38'—H38D	0.9700
C4—H4	0.9300	C39—C40	1.419 (4)
C5—C6	1.427 (4)	C40—C42	1.398 (4)
C6—C7	1.334 (4)	C40—C41	1.404 (4)
C6—H6	0.9300	C42—C43	1.388 (4)
C7—C8	1.432 (4)	C43—C44	1.417 (4)
C7—H7	0.9300	C43—C45	1.418 (4)
C8—C9	1.398 (4)	C46—C47	1.509 (9)
C8—C12	1.400 (3)	C46—H46A	0.9600
C9—C10	1.352 (4)	C46—H46B	0.9600
C9—H9	0.9300	C46—H46C	0.9600
C10—C11	1.401 (4)	C47—H47A	0.9700
C10—H10	0.9300	C47—H47B	0.9700
C11—H11A	0.9300	C46'—C47'	1.521 (9)
C13—C17	1.399 (3)	C46'—H46D	0.9600
C13—C24	1.418 (3)	C46'—H46E	0.9600
C14—C15	1.398 (4)	C46'—H46F	0.9600
C14—H14	0.9300	C47'—H47C	0.9700
C15—C16	1.357 (4)	C47'—H47D	0.9700
C15—H15	0.9300	C48—C49	1.389 (3)
C16—C17	1.401 (4)	C48—C52	1.401 (4)
C16—H16	0.9300	C49—C51	1.416 (4)
C17—C18	1.430 (4)	C49—C50	1.419 (4)
C18—C19	1.348 (4)	C52—C54	1.419 (4)
C18—H18	0.9300	C52—C53	1.422 (4)
N6—Fe1—N5	83.02 (8)	N5—C25—C29	123.8 (2)
N6—Fe1—N4	174.79 (7)	N5—C25—C36	115.8 (2)
N5—Fe1—N4	94.35 (8)	C29—C25—C36	120.3 (2)
N6—Fe1—N1	90.18 (7)	N5—C26—C27	122.3 (3)
N5—Fe1—N1	93.45 (7)	N5—C26—H26	118.8
N4—Fe1—N1	94.48 (8)	C27—C26—H26	118.8
N6—Fe1—N2	96.56 (8)	C28—C27—C26	120.3 (3)
N5—Fe1—N2	175.80 (7)	C28—C27—H27	119.9
N4—Fe1—N2	86.38 (7)	C26—C27—H27	119.9
N1—Fe1—N2	82.36 (7)	C27—C28—C29	119.7 (2)
N6—Fe1—N3	92.90 (8)	C27—C28—H28	120.2
N5—Fe1—N3	88.01 (7)	C29—C28—H28	120.2
N4—Fe1—N3	82.50 (8)	C25—C29—C28	116.5 (2)
N1—Fe1—N3	176.74 (8)	C25—C29—C30	117.7 (3)
N2—Fe1—N3	96.18 (7)	C28—C29—C30	125.7 (2)
C42—O1—C38	116.7 (6)	C31—C30—C29	121.6 (3)
C42—O1—C38'	123.4 (6)	C31—C30—H30	119.2
C48—O2—C47	116.9 (7)	C29—C30—H30	119.2
C48—O2—C47'	123.0 (7)	C30—C31—C32	121.6 (3)
H11—O1W—H12	108.7	C30—C31—H31	119.2
C2—N1—C1	116.7 (2)	C32—C31—H31	119.2
C2—N1—Fe1	130.32 (16)	C36—C32—C33	116.9 (2)
C1—N1—Fe1	112.96 (15)	C36—C32—C31	117.8 (3)
C11—N2—C12	117.2 (2)	C33—C32—C31	125.3 (3)
C11—N2—Fe1	130.11 (17)	C34—C33—C32	119.7 (3)
C12—N2—Fe1	112.15 (14)	C34—C33—H33	120.2
C14—N3—C13	117.4 (2)	C32—C33—H33	120.2
C14—N3—Fe1	129.94 (18)	C33—C34—C35	120.0 (3)
C13—N3—Fe1	112.52 (15)	C33—C34—H34	120.0
C23—N4—C24	116.6 (2)	C35—C34—H34	120.0
C23—N4—Fe1	129.93 (17)	N6—C35—C34	122.5 (2)
C24—N4—Fe1	113.38 (15)	N6—C35—H35	118.7
C26—N5—C25	117.4 (2)	C34—C35—H35	118.7
C26—N5—Fe1	129.83 (17)	N6—C36—C32	124.0 (2)
C25—N5—Fe1	112.78 (15)	N6—C36—C25	115.2 (2)
C35—N6—C36	116.9 (2)	C32—C36—C25	120.8 (2)
C35—N6—Fe1	129.92 (17)	C38—C37—H37A	109.5
C36—N6—Fe1	113.17 (15)	C38—C37—H37B	109.5
N1—C1—C5	123.7 (2)	H37A—C37—H37B	109.5
N1—C1—C12	115.5 (2)	C38—C37—H37C	109.5
C5—C1—C12	120.8 (2)	H37A—C37—H37C	109.5
N1—C2—C3	122.9 (2)	H37B—C37—H37C	109.5
N1—C2—H2	118.5	O1—C38—C37	109.1 (12)
C3—C2—H2	118.5	O1—C38—H38A	109.9
C4—C3—C2	120.2 (3)	C37—C38—H38A	109.9
C4—C3—H3	119.9	O1—C38—H38B	109.9
C2—C3—H3	119.9	C37—C38—H38B	109.9
C3—C4—C5	119.1 (2)	H38A—C38—H38B	108.3
C3—C4—H4	120.5	C38'—C37'—H37D	109.5
C5—C4—H4	120.5	C38'—C37'—H37E	109.5
C1—C5—C4	117.3 (2)	H37D—C37'—H37E	109.5
C1—C5—C6	117.5 (3)	C38'—C37'—H37F	109.5
C4—C5—C6	125.2 (3)	H37D—C37'—H37F	109.5
C7—C6—C5	122.2 (3)	H37E—C37'—H37F	109.5
C7—C6—H6	118.9	O1—C38'—C37'	103.5 (12)
C5—C6—H6	118.9	O1—C38'—H38C	111.1
C6—C7—C8	121.4 (3)	C37'—C38'—H38C	111.1
C6—C7—H7	119.3	O1—C38'—H38D	111.1
C8—C7—H7	119.3	C37'—C38'—H38D	111.1
C9—C8—C12	116.8 (2)	H38C—C38'—H38D	109.0
C9—C8—C7	125.3 (3)	N7—C39—C40	178.0 (3)
C12—C8—C7	117.9 (2)	C42—C40—C41	121.1 (2)
C10—C9—C8	119.3 (2)	C42—C40—C39	122.6 (2)
C10—C9—H9	120.4	C41—C40—C39	116.3 (3)
C8—C9—H9	120.4	N8—C41—C40	177.0 (4)
C9—C10—C11	120.9 (3)	O1—C42—C43	113.2 (2)
C9—C10—H10	119.6	O1—C42—C40	121.5 (2)
C11—C10—H10	119.6	C43—C42—C40	125.2 (2)
N2—C11—C10	121.9 (3)	C42—C43—C44	123.1 (3)
N2—C11—H11A	119.1	C42—C43—C45	121.1 (2)
C10—C11—H11A	119.1	C44—C43—C45	115.7 (3)
N2—C12—C8	123.9 (2)	N9—C44—C43	177.6 (3)
N2—C12—C1	115.9 (2)	N10—C45—C43	178.3 (3)
C8—C12—C1	120.2 (2)	C47—C46—H46A	109.5
N3—C13—C17	123.5 (2)	C47—C46—H46B	109.5
N3—C13—C24	116.1 (2)	H46A—C46—H46B	109.5
C17—C13—C24	120.3 (2)	C47—C46—H46C	109.5
N3—C14—C15	122.6 (3)	H46A—C46—H46C	109.5
N3—C14—H14	118.7	H46B—C46—H46C	109.5
C15—C14—H14	118.7	O2—C47—C46	106.0 (12)
C16—C15—C14	119.8 (3)	O2—C47—H47A	110.5
C16—C15—H15	120.1	C46—C47—H47A	110.5
C14—C15—H15	120.1	O2—C47—H47B	110.5
C15—C16—C17	119.8 (3)	C46—C47—H47B	110.5
C15—C16—H16	120.1	H47A—C47—H47B	108.7
C17—C16—H16	120.1	C47'—C46'—H46D	109.5
C13—C17—C16	116.8 (3)	C47'—C46'—H46E	109.5
C13—C17—C18	117.6 (3)	H46D—C46'—H46E	109.5
C16—C17—C18	125.5 (3)	C47'—C46'—H46F	109.5
C19—C18—C17	121.8 (3)	H46D—C46'—H46F	109.5
C19—C18—H18	119.1	H46E—C46'—H46F	109.5
C17—C18—H18	119.1	O2—C47'—C46'	105.4 (12)
C18—C19—C20	121.1 (3)	O2—C47'—H47C	110.7
C18—C19—H19	119.4	C46'—C47'—H47C	110.7
C20—C19—H19	119.4	O2—C47'—H47D	110.7
C24—C20—C21	117.2 (3)	C46'—C47'—H47D	110.7
C24—C20—C19	118.1 (3)	H47C—C47'—H47D	108.8
C21—C20—C19	124.7 (3)	O2—C48—C49	112.9 (2)
C22—C21—C20	119.3 (3)	O2—C48—C52	121.9 (2)
C22—C21—H21	120.3	C49—C48—C52	125.2 (2)
C20—C21—H21	120.3	C48—C49—C51	124.2 (2)
C21—C22—C23	119.9 (3)	C48—C49—C50	120.1 (2)
C21—C22—H22	120.0	C51—C49—C50	115.7 (2)
C23—C22—H22	120.0	N11—C50—C49	177.9 (3)
N4—C23—C22	123.3 (3)	N12—C51—C49	176.6 (3)
N4—C23—H23	118.4	C48—C52—C54	122.4 (3)
C22—C23—H23	118.4	C48—C52—C53	121.2 (2)
N4—C24—C20	123.7 (2)	C54—C52—C53	116.4 (3)
N4—C24—C13	115.4 (2)	N13—C53—C52	177.9 (3)
C20—C24—C13	120.9 (2)	N14—C54—C52	178.1 (4)
N6—Fe1—N1—C2	77.2 (2)	N3—C13—C17—C18	178.1 (2)
N5—Fe1—N1—C2	−5.8 (2)	C24—C13—C17—C18	−1.6 (4)
N4—Fe1—N1—C2	−100.5 (2)	C15—C16—C17—C13	1.2 (4)
N2—Fe1—N1—C2	173.8 (2)	C15—C16—C17—C18	−178.5 (3)
N6—Fe1—N1—C1	−104.61 (16)	C13—C17—C18—C19	−0.5 (4)
N5—Fe1—N1—C1	172.37 (16)	C16—C17—C18—C19	179.2 (3)
N4—Fe1—N1—C1	77.72 (16)	C17—C18—C19—C20	1.5 (5)
N2—Fe1—N1—C1	−8.02 (15)	C18—C19—C20—C24	−0.3 (4)
N6—Fe1—N2—C11	−89.7 (2)	C18—C19—C20—C21	179.6 (3)
N4—Fe1—N2—C11	86.0 (2)	C24—C20—C21—C22	0.1 (4)
N1—Fe1—N2—C11	−179.0 (2)	C19—C20—C21—C22	−179.8 (3)
N3—Fe1—N2—C11	3.9 (2)	C20—C21—C22—C23	1.1 (4)
N6—Fe1—N2—C12	98.77 (15)	C24—N4—C23—C22	−0.6 (3)
N4—Fe1—N2—C12	−85.53 (15)	Fe1—N4—C23—C22	−176.88 (18)
N1—Fe1—N2—C12	9.48 (15)	C21—C22—C23—N4	−0.9 (4)
N3—Fe1—N2—C12	−167.58 (15)	C23—N4—C24—C20	1.9 (3)
N6—Fe1—N3—C14	0.1 (2)	Fe1—N4—C24—C20	178.83 (19)
N5—Fe1—N3—C14	83.0 (2)	C23—N4—C24—C13	−178.1 (2)
N4—Fe1—N3—C14	177.6 (2)	Fe1—N4—C24—C13	−1.2 (2)
N2—Fe1—N3—C14	−96.8 (2)	C21—C20—C24—N4	−1.7 (4)
N6—Fe1—N3—C13	−175.51 (15)	C19—C20—C24—N4	178.2 (2)
N5—Fe1—N3—C13	−92.61 (15)	C21—C20—C24—C13	178.4 (2)
N4—Fe1—N3—C13	2.05 (15)	C19—C20—C24—C13	−1.7 (4)
N2—Fe1—N3—C13	87.56 (15)	N3—C13—C24—N4	3.1 (3)
N5—Fe1—N4—C23	−96.6 (2)	C17—C13—C24—N4	−177.2 (2)
N1—Fe1—N4—C23	−2.8 (2)	N3—C13—C24—C20	−177.0 (2)
N2—Fe1—N4—C23	79.2 (2)	C17—C13—C24—C20	2.7 (3)
N3—Fe1—N4—C23	176.0 (2)	C26—N5—C25—C29	0.5 (3)
N5—Fe1—N4—C24	86.99 (15)	Fe1—N5—C25—C29	179.39 (17)
N1—Fe1—N4—C24	−179.20 (15)	C26—N5—C25—C36	−179.68 (19)
N2—Fe1—N4—C24	−97.16 (15)	Fe1—N5—C25—C36	−0.8 (2)
N3—Fe1—N4—C24	−0.43 (15)	C25—N5—C26—C27	0.5 (3)
N6—Fe1—N5—C26	179.6 (2)	Fe1—N5—C26—C27	−178.19 (18)
N4—Fe1—N5—C26	4.2 (2)	N5—C26—C27—C28	−0.9 (4)
N1—Fe1—N5—C26	−90.6 (2)	C26—C27—C28—C29	0.4 (4)
N3—Fe1—N5—C26	86.5 (2)	N5—C25—C29—C28	−1.0 (3)
N6—Fe1—N5—C25	0.94 (14)	C36—C25—C29—C28	179.2 (2)
N4—Fe1—N5—C25	−174.54 (14)	N5—C25—C29—C30	−179.9 (2)
N1—Fe1—N5—C25	90.70 (15)	C36—C25—C29—C30	0.3 (3)
N3—Fe1—N5—C25	−92.22 (15)	C27—C28—C29—C25	0.5 (4)
N5—Fe1—N6—C35	179.3 (2)	C27—C28—C29—C30	179.3 (2)
N1—Fe1—N6—C35	85.9 (2)	C25—C29—C30—C31	0.6 (4)
N2—Fe1—N6—C35	3.5 (2)	C28—C29—C30—C31	−178.2 (3)
N5—Fe1—N6—C36	−0.92 (14)	C29—C30—C31—C32	−0.9 (4)
N1—Fe1—N6—C36	−94.38 (15)	C30—C31—C32—C36	0.4 (4)
N2—Fe1—N6—C36	−176.71 (14)	C30—C31—C32—C33	−179.0 (3)
N3—Fe1—N6—C36	86.72 (15)	C36—C32—C33—C34	−0.4 (4)
C2—N1—C1—C5	3.4 (3)	C31—C32—C33—C34	179.0 (2)
Fe1—N1—C1—C5	−175.04 (18)	C32—C33—C34—C35	1.1 (4)
C2—N1—C1—C12	−176.4 (2)	C36—N6—C35—C34	−0.5 (3)
Fe1—N1—C1—C12	5.2 (3)	Fe1—N6—C35—C34	179.29 (18)
C1—N1—C2—C3	−0.6 (4)	C33—C34—C35—N6	−0.7 (4)
Fe1—N1—C2—C3	177.50 (19)	C35—N6—C36—C32	1.2 (3)
N1—C2—C3—C4	−2.1 (4)	Fe1—N6—C36—C32	−178.56 (17)
C2—C3—C4—C5	2.0 (4)	C35—N6—C36—C25	−179.46 (19)
N1—C1—C5—C4	−3.4 (4)	Fe1—N6—C36—C25	0.7 (2)
C12—C1—C5—C4	176.4 (2)	C33—C32—C36—N6	−0.8 (3)
N1—C1—C5—C6	176.5 (2)	C31—C32—C36—N6	179.7 (2)
C12—C1—C5—C6	−3.7 (4)	C33—C32—C36—C25	179.9 (2)
C3—C4—C5—C1	0.5 (4)	C31—C32—C36—C25	0.5 (3)
C3—C4—C5—C6	−179.4 (3)	N5—C25—C36—N6	0.0 (3)
C1—C5—C6—C7	1.9 (4)	C29—C25—C36—N6	179.86 (19)
C4—C5—C6—C7	−178.2 (3)	N5—C25—C36—C32	179.37 (19)
C5—C6—C7—C8	1.0 (5)	C29—C25—C36—C32	−0.8 (3)
C6—C7—C8—C9	177.4 (3)	C42—O1—C38—C37	−178.4 (7)
C6—C7—C8—C12	−2.0 (4)	C42—O1—C38'—C37'	143.5 (8)
C12—C8—C9—C10	1.0 (4)	C38—O1—C42—C43	−136.6 (6)
C7—C8—C9—C10	−178.5 (3)	C38'—O1—C42—C43	−162.0 (5)
C8—C9—C10—C11	−0.7 (4)	C38—O1—C42—C40	44.9 (6)
C12—N2—C11—C10	1.9 (4)	C38'—O1—C42—C40	19.5 (6)
Fe1—N2—C11—C10	−169.21 (19)	C41—C40—C42—O1	−156.7 (3)
C9—C10—C11—N2	−0.8 (4)	C39—C40—C42—O1	22.8 (4)
C11—N2—C12—C8	−1.7 (3)	C41—C40—C42—C43	24.9 (4)
Fe1—N2—C12—C8	171.01 (19)	C39—C40—C42—C43	−155.6 (3)
C11—N2—C12—C1	177.9 (2)	O1—C42—C43—C44	−161.2 (2)
Fe1—N2—C12—C1	−9.4 (2)	C40—C42—C43—C44	17.4 (4)
C9—C8—C12—N2	0.2 (4)	O1—C42—C43—C45	15.6 (3)
C7—C8—C12—N2	179.7 (2)	C40—C42—C43—C45	−165.9 (3)
C9—C8—C12—C1	−179.3 (2)	C48—O2—C47—C46	164.3 (7)
C7—C8—C12—C1	0.2 (3)	C47'—O2—C47—C46	−76 (6)
N1—C1—C12—N2	2.9 (3)	C48—O2—C47'—C46'	128.5 (8)
C5—C1—C12—N2	−176.9 (2)	C47—O2—C48—C49	−133.8 (8)
N1—C1—C12—C8	−177.5 (2)	C47'—O2—C48—C49	−148.0 (8)
C5—C1—C12—C8	2.7 (3)	C47—O2—C48—C52	47.5 (9)
C14—N3—C13—C17	0.8 (3)	C47'—O2—C48—C52	33.3 (9)
Fe1—N3—C13—C17	176.96 (18)	O2—C48—C49—C51	−162.4 (2)
C14—N3—C13—C24	−179.5 (2)	C52—C48—C49—C51	16.3 (4)
Fe1—N3—C13—C24	−3.3 (2)	O2—C48—C49—C50	15.0 (3)
C13—N3—C14—C15	0.4 (3)	C52—C48—C49—C50	−166.3 (2)
Fe1—N3—C14—C15	−174.98 (19)	O2—C48—C52—C54	18.5 (4)
N3—C14—C15—C16	−0.7 (4)	C49—C48—C52—C54	−160.1 (3)
C14—C15—C16—C17	−0.1 (4)	O2—C48—C52—C53	−162.8 (2)
N3—C13—C17—C16	−1.6 (4)	C49—C48—C52—C53	18.7 (4)
C24—C13—C17—C16	178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···N7	0.84	2.17	2.996 (5)	169
O1w—H12···N8i	0.84	2.25	3.078 (5)	169

Table 1

Selected bond lengths (Å)

Fe1—N6	1.9563 (19)
Fe1—N5	1.9654 (18)
Fe1—N4	1.9686 (19)
Fe1—N1	1.9752 (18)
Fe1—N2	1.9819 (18)
Fe1—N3	1.9836 (18)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯N7	0.84	2.17	2.996 (5)	169
O1w—H12⋯N8i	0.84	2.25	3.078 (5)	169

Symmetry code: (i) .