Tris(acetonitrile-κN){2,6-bis-[(diphenyl-phosphan-yl)amino]-4-eth-oxy-1,3,5-triazine-κP,N,P'}iron(II) bis-(tetra-fluorido-borate) acetonitrile disolvate.

In the title compound, [Fe(CH(3)CN)(3)(C(29)H(27)N(5)OP(2))](BF(4))(2)·2CH(3)CN, the Fe(II) ion is octa-hedrally coordinated by a meridionally chelating tridentate pincer-type PNP ligand derived from 2,6-diamino-4-eth-oxy-1,3,5-triazine and by three acetonitrile mol-ecules. The four Fe-N bond lengths range from 1.9142 (12) to 1.9579 (11) Å, while the Fe-P bonds are 2.2452 (4) and 2.2506 (4) Å [P-Fe-P = 165.523 (14)°], consistent with Fe(II) in a low-spin state. Unlike related Fe PNP complexes based on 2,6-diamino-pyridine, the BF(4) anions are not hydrogen bonded to the two NH groups of the pincer ligand but show instead anion-π inter-actions with the triazine ring and acetonitrile mol-ecules in addition to ten C-H⋯F inter-actions. Most remarkable among these is an anion-π(triazine) inter-action with a short distance of 2.788 (2) Å between one F and the centroid of the π-acidic triazine ring. The corresponding shortest distance between this F atom and a triazine carbon atom is 2.750 (2) Å. The two NH groups of the pincer ligand donate N-H⋯N hydrogen bonds to the triazine N atom of a neighbouring complex and to an uncoordinated acetonitrile mol-ecule. This last mol-ecule is in a side-on head-to-tail association with the second uncoordinated acetonitrile at C⋯N distances of 3.467 (2) and 3.569 (2) Å. In contrast to several related compounds with diamino-pyridine- instead of diamino-triazine-based PNP ligands, the title crystal structure is remarkably well ordered. This suggests that the diamino-triazine moiety exerts notable crystal structure stabilizing effects.

Related literature

For a review on class="Chemical">PNclass="Chemical">pan class="Chemical">P and PCP pincer complexes based on 2,6-diamino­pyridine and 1,3-diamino­benzene, see: Benito-Garagorri & Kirchner (2008 ▶). For the crystal structures of related PNP pincer complexes, see: Benito-Garagorri et al. (2006 ▶). For weak hydrogen bonds, see Desiraju & Steiner (1999 ▶). For anion–π inter­actions, see Gamez et al. (2007 ▶); Mooibroek et al. (2008 ▶); Manzano et al. (2008 ▶); Quinonero et al. (2010 ▶); Lu et al. (2009 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

[class="Chemical">Fe(C2H3N)3(class="Chemical">pan class="CellLine">C29H27N5OP2)](BF4)2·2C2H3N

M = 958.24

Triclinic,

a = 8.8548 (4) Å

b = 13.8402 (7) Å

c = 20.1352 (10) Å

α = 71.399 (2)°

β = 82.731 (2)°

γ = 72.789 (2)°

V = 2232.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.49 mm−1

T = 100 K

0.58 × 0.36 × 0.30 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.74, T max = 0.86

26262 measured reflections

12688 independent reflections

11076 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.03

12688 reflections

573 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: pan class="Chemical">PLATON (Sclass="Chemical">pek, 2009 ▶) and class="Chemical">publCIF (Westriclass="Chemical">p, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049804/gk2437sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049804/gk2437Isup2.hkl

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

[Fe(C2H3N)3(C29H27N5OP2)](BF4)2·2C2H3N	Z = 2
Mr = 958.24	F(000) = 984
Triclinic, P1	Dx = 1.425 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8548 (4) Å	Cell parameters from 8213 reflections
b = 13.8402 (7) Å	θ = 2.5–30.0°
c = 20.1352 (10) Å	µ = 0.49 mm−1
α = 71.399 (2)°	T = 100 K
β = 82.731 (2)°	Block, orange
γ = 72.789 (2)°	0.58 × 0.36 × 0.30 mm
V = 2232.6 (2) Å3

Bruker SMART APEX CCD diffractometer	12688 independent reflections
Radiation source: fine-focus sealed tube	11076 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω scans	θmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −12→12
Tmin = 0.74, Tmax = 0.86	k = −17→19
26262 measured reflections	l = −28→28

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.9995P] where P = (Fo2 + 2Fc2)/3
12688 reflections	(Δ/σ)max = 0.002
573 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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. 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.

	x	y	z	Uiso*/Ueq
Fe1	0.54460 (2)	0.690690 (14)	0.254170 (9)	0.01419 (5)
P1	0.53830 (4)	0.61385 (3)	0.172145 (16)	0.01517 (7)
P2	0.54736 (4)	0.72777 (3)	0.354940 (17)	0.01594 (7)
O1	0.37867 (13)	0.30944 (8)	0.44745 (5)	0.0222 (2)
N1	0.49244 (12)	0.56374 (8)	0.31769 (5)	0.01485 (19)
N2	0.41916 (13)	0.40539 (9)	0.33384 (6)	0.0170 (2)
N3	0.44824 (13)	0.45696 (9)	0.43304 (6)	0.0180 (2)
N4	0.47666 (13)	0.50736 (9)	0.22341 (5)	0.0166 (2)
H4N	0.4542	0.4641	0.2046	0.020*
N5	0.50809 (13)	0.61675 (9)	0.41348 (6)	0.0172 (2)
H5N	0.5047	0.6076	0.4589	0.021*
N6	0.59524 (13)	0.81386 (9)	0.18835 (6)	0.0181 (2)
N7	0.76688 (13)	0.62306 (9)	0.26069 (6)	0.0186 (2)
N8	0.32155 (13)	0.75857 (9)	0.24727 (6)	0.0174 (2)
C1	0.46287 (14)	0.49058 (10)	0.29390 (6)	0.0156 (2)
C2	0.41678 (15)	0.39247 (10)	0.40219 (7)	0.0175 (2)
C3	0.48238 (14)	0.54323 (10)	0.38838 (6)	0.0158 (2)
C4	0.72769 (15)	0.55979 (11)	0.13392 (7)	0.0190 (2)
C5	0.79139 (17)	0.63019 (12)	0.07949 (8)	0.0250 (3)
H5	0.7292	0.7005	0.0594	0.030*
C6	0.94560 (19)	0.59708 (14)	0.05485 (9)	0.0343 (4)
H6	0.9893	0.6448	0.0180	0.041*
C7	1.0360 (2)	0.49401 (16)	0.08419 (10)	0.0397 (4)
H7	1.1416	0.4714	0.0672	0.048*
C8	0.9733 (2)	0.42420 (15)	0.13793 (11)	0.0412 (4)
H8	1.0355	0.3537	0.1575	0.049*
C9	0.81891 (18)	0.45712 (13)	0.16341 (9)	0.0304 (3)
H9	0.7763	0.4095	0.2008	0.036*
C10	0.41181 (15)	0.67008 (10)	0.09752 (7)	0.0177 (2)
C11	0.32052 (16)	0.77537 (11)	0.08017 (7)	0.0198 (2)
H11	0.3232	0.8188	0.1080	0.024*
C12	0.22525 (16)	0.81685 (11)	0.02197 (7)	0.0225 (3)
H12	0.1615	0.8881	0.0108	0.027*
C13	0.22351 (17)	0.75411 (12)	−0.01961 (7)	0.0246 (3)
H13	0.1597	0.7829	−0.0596	0.030*
C14	0.31498 (18)	0.64906 (12)	−0.00290 (7)	0.0248 (3)
H14	0.3132	0.6063	−0.0313	0.030*
C15	0.40884 (17)	0.60697 (11)	0.05546 (7)	0.0217 (3)
H15	0.4711	0.5354	0.0669	0.026*
C16	0.72838 (16)	0.72989 (11)	0.38677 (7)	0.0206 (2)
C17	0.75249 (19)	0.82516 (13)	0.38679 (8)	0.0269 (3)
H17	0.6729	0.8899	0.3709	0.032*
C18	0.8950 (2)	0.82454 (16)	0.41049 (9)	0.0363 (4)
H18	0.9121	0.8891	0.4105	0.044*
C19	1.0107 (2)	0.73052 (17)	0.43381 (9)	0.0394 (4)
H19	1.1063	0.7306	0.4504	0.047*
C20	0.9880 (2)	0.63569 (15)	0.43311 (9)	0.0349 (4)
H20	1.0687	0.5714	0.4485	0.042*
C21	0.84664 (18)	0.63495 (13)	0.40975 (8)	0.0262 (3)
H21	0.8307	0.5701	0.4095	0.031*
C22	0.39861 (16)	0.84083 (10)	0.37039 (7)	0.0188 (2)
C23	0.35655 (19)	0.93268 (11)	0.31328 (8)	0.0254 (3)
H23	0.4041	0.9334	0.2682	0.030*
C24	0.2454 (2)	1.02256 (12)	0.32279 (9)	0.0301 (3)
H24	0.2179	1.0848	0.2842	0.036*
C25	0.17431 (18)	1.02166 (12)	0.38861 (9)	0.0273 (3)
H25	0.0985	1.0832	0.3950	0.033*
C26	0.21456 (18)	0.93031 (12)	0.44505 (8)	0.0257 (3)
H26	0.1652	0.9294	0.4899	0.031*
C27	0.32680 (16)	0.84016 (11)	0.43620 (7)	0.0213 (2)
H27	0.3544	0.7782	0.4750	0.026*
C28	0.62945 (17)	0.88174 (11)	0.14559 (7)	0.0217 (3)
C29	0.6739 (2)	0.96728 (13)	0.08967 (8)	0.0333 (3)
H29A	0.7501	0.9373	0.0568	0.050*
H29B	0.7220	1.0062	0.1100	0.050*
H29C	0.5795	1.0156	0.0647	0.050*
C30	0.89967 (17)	0.58461 (12)	0.26125 (8)	0.0247 (3)
C31	1.07032 (19)	0.53667 (16)	0.26182 (11)	0.0416 (4)
H31A	1.0920	0.4598	0.2722	0.062*
H31B	1.1157	0.5524	0.2978	0.062*
H31C	1.1178	0.5657	0.2158	0.062*
C32	0.18977 (17)	0.79880 (12)	0.24244 (7)	0.0237 (3)
C33	0.0217 (2)	0.85205 (18)	0.23351 (11)	0.0480 (5)
H33A	−0.0404	0.8049	0.2627	0.072*
H33B	−0.0031	0.8702	0.1842	0.072*
H33C	−0.0044	0.9168	0.2476	0.072*
C34	0.33860 (19)	0.23392 (12)	0.42023 (8)	0.0251 (3)
H34A	0.2883	0.2717	0.3744	0.030*
H34B	0.2621	0.2010	0.4531	0.030*
C35	0.4844 (2)	0.14967 (16)	0.41153 (13)	0.0453 (5)
H35A	0.4561	0.0999	0.3932	0.068*
H35B	0.5331	0.1116	0.4570	0.068*
H35C	0.5595	0.1823	0.3786	0.068*
B1	0.1509 (2)	1.07050 (13)	0.09763 (9)	0.0251 (3)
F1	0.28453 (14)	0.99849 (9)	0.12992 (8)	0.0545 (4)
F2	0.07067 (14)	1.13034 (11)	0.14131 (7)	0.0484 (3)
F3	0.19089 (18)	1.13810 (10)	0.03575 (6)	0.0520 (3)
F4	0.05329 (13)	1.01714 (8)	0.08354 (6)	0.0381 (2)
B2	0.9016 (2)	0.31898 (14)	0.36767 (10)	0.0294 (3)
F5	0.89457 (19)	0.22855 (9)	0.42061 (6)	0.0566 (4)
F6	0.9380 (2)	0.39051 (10)	0.39354 (7)	0.0579 (4)
F7	0.76148 (14)	0.36553 (11)	0.33321 (8)	0.0555 (3)
F8	1.01956 (13)	0.29184 (9)	0.31804 (6)	0.0414 (2)
N9	0.4500 (2)	0.34626 (12)	0.16629 (8)	0.0379 (3)
C36	0.4224 (2)	0.28836 (13)	0.14368 (9)	0.0306 (3)
C37	0.3876 (2)	0.21599 (16)	0.11259 (12)	0.0427 (4)
H37A	0.4103	0.1447	0.1460	0.064*
H37B	0.4534	0.2146	0.0698	0.064*
H37C	0.2757	0.2400	0.1011	0.064*
N10	0.6755 (2)	0.04815 (13)	0.23086 (9)	0.0414 (4)
C38	0.7314 (2)	0.10238 (14)	0.24545 (9)	0.0329 (3)
C39	0.8041 (3)	0.17130 (19)	0.26401 (12)	0.0490 (5)
H39A	0.7233	0.2363	0.2663	0.073*
H39B	0.8859	0.1893	0.2285	0.073*
H39C	0.8521	0.1348	0.3098	0.073*

	U11	U22	U33	U12	U13	U23
Fe1	0.01216 (9)	0.01347 (9)	0.01552 (8)	−0.00280 (6)	−0.00222 (6)	−0.00238 (6)
P1	0.01333 (14)	0.01522 (14)	0.01542 (14)	−0.00266 (11)	−0.00135 (10)	−0.00328 (11)
P2	0.01639 (15)	0.01461 (14)	0.01681 (14)	−0.00473 (11)	−0.00263 (11)	−0.00341 (11)
O1	0.0305 (5)	0.0196 (5)	0.0184 (4)	−0.0128 (4)	−0.0006 (4)	−0.0027 (4)
N1	0.0135 (5)	0.0144 (5)	0.0160 (5)	−0.0027 (4)	−0.0017 (3)	−0.0041 (4)
N2	0.0165 (5)	0.0171 (5)	0.0178 (5)	−0.0054 (4)	−0.0026 (4)	−0.0039 (4)
N3	0.0205 (5)	0.0172 (5)	0.0163 (5)	−0.0061 (4)	−0.0021 (4)	−0.0035 (4)
N4	0.0187 (5)	0.0161 (5)	0.0157 (5)	−0.0055 (4)	−0.0015 (4)	−0.0047 (4)
N5	0.0224 (5)	0.0157 (5)	0.0141 (4)	−0.0067 (4)	−0.0021 (4)	−0.0030 (4)
N6	0.0166 (5)	0.0181 (5)	0.0191 (5)	−0.0036 (4)	−0.0031 (4)	−0.0051 (4)
N7	0.0179 (5)	0.0180 (5)	0.0191 (5)	−0.0054 (4)	−0.0035 (4)	−0.0027 (4)
N8	0.0182 (5)	0.0162 (5)	0.0169 (5)	−0.0043 (4)	−0.0014 (4)	−0.0039 (4)
C1	0.0119 (5)	0.0162 (5)	0.0175 (5)	−0.0016 (4)	−0.0033 (4)	−0.0043 (4)
C2	0.0160 (5)	0.0162 (5)	0.0192 (5)	−0.0048 (4)	−0.0022 (4)	−0.0025 (4)
C3	0.0136 (5)	0.0161 (5)	0.0170 (5)	−0.0027 (4)	−0.0027 (4)	−0.0043 (4)
C4	0.0147 (6)	0.0213 (6)	0.0196 (6)	−0.0024 (5)	0.0001 (4)	−0.0066 (5)
C5	0.0201 (6)	0.0246 (7)	0.0257 (6)	−0.0045 (5)	0.0017 (5)	−0.0038 (5)
C6	0.0232 (7)	0.0366 (9)	0.0357 (8)	−0.0076 (6)	0.0085 (6)	−0.0050 (7)
C7	0.0205 (7)	0.0434 (10)	0.0447 (10)	0.0003 (7)	0.0094 (6)	−0.0109 (8)
C8	0.0260 (8)	0.0319 (9)	0.0481 (10)	0.0067 (6)	0.0080 (7)	−0.0049 (7)
C9	0.0222 (7)	0.0241 (7)	0.0340 (8)	0.0006 (5)	0.0045 (6)	−0.0024 (6)
C10	0.0148 (5)	0.0186 (6)	0.0177 (5)	−0.0037 (4)	−0.0021 (4)	−0.0028 (4)
C11	0.0187 (6)	0.0180 (6)	0.0204 (6)	−0.0042 (5)	−0.0017 (4)	−0.0030 (5)
C12	0.0193 (6)	0.0214 (6)	0.0213 (6)	−0.0035 (5)	−0.0032 (5)	−0.0001 (5)
C13	0.0205 (6)	0.0303 (7)	0.0199 (6)	−0.0059 (5)	−0.0053 (5)	−0.0024 (5)
C14	0.0246 (7)	0.0291 (7)	0.0223 (6)	−0.0061 (5)	−0.0043 (5)	−0.0096 (5)
C15	0.0212 (6)	0.0210 (6)	0.0215 (6)	−0.0027 (5)	−0.0034 (5)	−0.0061 (5)
C16	0.0208 (6)	0.0246 (6)	0.0181 (5)	−0.0100 (5)	−0.0034 (4)	−0.0041 (5)
C17	0.0311 (8)	0.0287 (7)	0.0256 (7)	−0.0168 (6)	−0.0019 (5)	−0.0059 (6)
C18	0.0395 (9)	0.0452 (10)	0.0345 (8)	−0.0295 (8)	−0.0038 (7)	−0.0083 (7)
C19	0.0312 (8)	0.0605 (12)	0.0317 (8)	−0.0271 (8)	−0.0087 (6)	−0.0043 (8)
C20	0.0238 (7)	0.0455 (10)	0.0307 (8)	−0.0093 (7)	−0.0107 (6)	−0.0012 (7)
C21	0.0221 (7)	0.0292 (7)	0.0254 (6)	−0.0069 (5)	−0.0069 (5)	−0.0034 (5)
C22	0.0196 (6)	0.0158 (5)	0.0223 (6)	−0.0052 (4)	−0.0033 (4)	−0.0061 (5)
C23	0.0305 (7)	0.0185 (6)	0.0242 (6)	−0.0045 (5)	−0.0016 (5)	−0.0042 (5)
C24	0.0352 (8)	0.0175 (6)	0.0330 (8)	−0.0024 (6)	−0.0050 (6)	−0.0042 (6)
C25	0.0235 (7)	0.0211 (6)	0.0378 (8)	−0.0020 (5)	−0.0040 (6)	−0.0121 (6)
C26	0.0229 (7)	0.0265 (7)	0.0289 (7)	−0.0049 (5)	−0.0002 (5)	−0.0117 (6)
C27	0.0203 (6)	0.0205 (6)	0.0229 (6)	−0.0054 (5)	−0.0024 (5)	−0.0059 (5)
C28	0.0238 (6)	0.0191 (6)	0.0220 (6)	−0.0058 (5)	−0.0006 (5)	−0.0057 (5)
C29	0.0493 (10)	0.0230 (7)	0.0264 (7)	−0.0169 (7)	0.0069 (6)	−0.0024 (6)
C30	0.0189 (6)	0.0245 (7)	0.0287 (7)	−0.0054 (5)	−0.0039 (5)	−0.0043 (5)
C31	0.0157 (7)	0.0446 (10)	0.0570 (11)	−0.0010 (7)	−0.0057 (7)	−0.0098 (9)
C32	0.0206 (6)	0.0239 (6)	0.0205 (6)	−0.0027 (5)	−0.0002 (5)	−0.0016 (5)
C33	0.0188 (8)	0.0557 (12)	0.0434 (10)	0.0061 (7)	0.0010 (7)	0.0049 (9)
C34	0.0328 (7)	0.0229 (7)	0.0247 (6)	−0.0170 (6)	−0.0021 (5)	−0.0047 (5)
C35	0.0432 (10)	0.0356 (9)	0.0685 (13)	−0.0085 (8)	−0.0112 (9)	−0.0292 (9)
B1	0.0253 (8)	0.0208 (7)	0.0277 (7)	−0.0038 (6)	−0.0059 (6)	−0.0054 (6)
F1	0.0397 (6)	0.0273 (5)	0.0937 (10)	0.0018 (5)	−0.0371 (6)	−0.0110 (6)
F2	0.0350 (6)	0.0698 (8)	0.0522 (7)	−0.0098 (6)	0.0023 (5)	−0.0398 (6)
F3	0.0873 (10)	0.0522 (7)	0.0275 (5)	−0.0418 (7)	0.0037 (5)	−0.0080 (5)
F4	0.0372 (5)	0.0315 (5)	0.0483 (6)	−0.0118 (4)	−0.0163 (4)	−0.0078 (4)
B2	0.0302 (9)	0.0228 (8)	0.0311 (8)	−0.0014 (6)	−0.0074 (7)	−0.0052 (6)
F5	0.0906 (10)	0.0270 (5)	0.0376 (6)	−0.0083 (6)	0.0169 (6)	−0.0043 (5)
F6	0.0923 (11)	0.0402 (7)	0.0487 (7)	−0.0204 (7)	−0.0164 (7)	−0.0158 (5)
F7	0.0288 (6)	0.0589 (8)	0.0708 (8)	0.0107 (5)	−0.0183 (5)	−0.0231 (7)
F8	0.0290 (5)	0.0476 (6)	0.0451 (6)	−0.0080 (5)	0.0026 (4)	−0.0139 (5)
N9	0.0545 (10)	0.0293 (7)	0.0345 (7)	−0.0144 (7)	−0.0054 (6)	−0.0115 (6)
C36	0.0304 (8)	0.0252 (7)	0.0371 (8)	−0.0069 (6)	−0.0031 (6)	−0.0106 (6)
C37	0.0330 (9)	0.0388 (10)	0.0683 (13)	−0.0096 (7)	−0.0059 (8)	−0.0308 (9)
N10	0.0441 (9)	0.0342 (8)	0.0459 (9)	−0.0092 (7)	−0.0028 (7)	−0.0128 (7)
C38	0.0322 (8)	0.0284 (8)	0.0324 (8)	−0.0019 (6)	−0.0014 (6)	−0.0071 (6)
C39	0.0472 (12)	0.0539 (12)	0.0558 (12)	−0.0206 (10)	0.0016 (9)	−0.0248 (10)

Fe1—N1	1.9579 (11)	C18—H18	0.9500
Fe1—N6	1.9298 (11)	C19—C20	1.390 (3)
Fe1—N7	1.9142 (12)	C19—H19	0.9500
Fe1—N8	1.9211 (11)	C20—C21	1.395 (2)
Fe1—P1	2.2452 (4)	C20—H20	0.9500
Fe1—P2	2.2506 (4)	C21—H21	0.9500
P1—N4	1.7025 (11)	C22—C27	1.3938 (19)
P1—C4	1.8063 (13)	C22—C23	1.4046 (19)
P1—C10	1.8116 (13)	C23—C24	1.390 (2)
P2—N5	1.7113 (11)	C23—H23	0.9500
P2—C22	1.8075 (14)	C24—C25	1.391 (2)
P2—C16	1.8113 (14)	C24—H24	0.9500
O1—C2	1.3222 (15)	C25—C26	1.391 (2)
O1—C34	1.4673 (17)	C25—H25	0.9500
N1—C1	1.3495 (16)	C26—C27	1.393 (2)
N1—C3	1.3564 (16)	C26—H26	0.9500
N2—C2	1.3284 (16)	C27—H27	0.9500
N2—C1	1.3315 (16)	C28—C29	1.4620 (19)
N3—C3	1.3362 (16)	C29—H29A	0.9800
N3—C2	1.3434 (17)	C29—H29B	0.9800
N4—C1	1.3587 (16)	C29—H29C	0.9800
N4—H4N	0.8800	C30—C31	1.459 (2)
N5—C3	1.3553 (16)	C31—H31A	0.9800
N5—H5N	0.8800	C31—H31B	0.9800
N6—C28	1.1411 (18)	C31—H31C	0.9800
N7—C30	1.1380 (19)	C32—C33	1.457 (2)
N8—C32	1.1361 (19)	C33—H33A	0.9800
C4—C9	1.3885 (19)	C33—H33B	0.9800
C4—C5	1.3987 (19)	C33—H33C	0.9800
C5—C6	1.387 (2)	C34—C35	1.497 (3)
C5—H5	0.9500	C34—H34A	0.9900
C6—C7	1.390 (2)	C34—H34B	0.9900
C6—H6	0.9500	C35—H35A	0.9800
C7—C8	1.382 (3)	C35—H35B	0.9800
C7—H7	0.9500	C35—H35C	0.9800
C8—C9	1.394 (2)	B1—F3	1.376 (2)
C8—H8	0.9500	B1—F1	1.378 (2)
C9—H9	0.9500	B1—F2	1.387 (2)
C10—C11	1.3960 (18)	B1—F4	1.395 (2)
C10—C15	1.4042 (19)	B2—F5	1.373 (2)
C11—C12	1.3961 (18)	B2—F7	1.377 (2)
C11—H11	0.9500	B2—F6	1.384 (2)
C12—C13	1.389 (2)	B2—F8	1.405 (2)
C12—H12	0.9500	N9—C36	1.134 (2)
C13—C14	1.394 (2)	C36—C37	1.457 (2)
C13—H13	0.9500	C37—H37A	0.9800
C14—C15	1.3911 (19)	C37—H37B	0.9800
C14—H14	0.9500	C37—H37C	0.9800
C15—H15	0.9500	N10—C38	1.137 (2)
C16—C17	1.397 (2)	C38—C39	1.454 (3)
C16—C21	1.399 (2)	C39—H39A	0.9800
C17—C18	1.401 (2)	C39—H39B	0.9800
C17—H17	0.9500	C39—H39C	0.9800
C18—C19	1.381 (3)
N7—Fe1—N8	179.78 (5)	C16—C17—H17	120.3
N7—Fe1—N6	88.04 (5)	C18—C17—H17	120.3
N8—Fe1—N6	91.87 (5)	C19—C18—C17	120.32 (16)
N7—Fe1—N1	92.09 (5)	C19—C18—H18	119.8
N8—Fe1—N1	87.99 (4)	C17—C18—H18	119.8
N6—Fe1—N1	177.64 (4)	C18—C19—C20	120.39 (15)
N7—Fe1—P1	88.65 (4)	C18—C19—H19	119.8
N8—Fe1—P1	91.16 (3)	C20—C19—H19	119.8
N6—Fe1—P1	94.65 (3)	C19—C20—C21	119.99 (16)
N1—Fe1—P1	83.00 (3)	C19—C20—H20	120.0
N7—Fe1—P2	89.37 (4)	C21—C20—H20	120.0
N8—Fe1—P2	90.84 (3)	C20—C21—C16	119.83 (15)
N6—Fe1—P2	99.61 (3)	C20—C21—H21	120.1
N1—Fe1—P2	82.74 (3)	C16—C21—H21	120.1
P1—Fe1—P2	165.523 (14)	C27—C22—C23	119.57 (13)
N4—P1—C4	105.65 (6)	C27—C22—P2	122.65 (10)
N4—P1—C10	105.10 (6)	C23—C22—P2	117.78 (11)
C4—P1—C10	102.57 (6)	C24—C23—C22	119.99 (14)
N4—P1—Fe1	99.37 (4)	C24—C23—H23	120.0
C4—P1—Fe1	115.85 (5)	C22—C23—H23	120.0
C10—P1—Fe1	126.17 (5)	C23—C24—C25	120.26 (14)
N5—P2—C22	107.23 (6)	C23—C24—H24	119.9
N5—P2—C16	102.50 (6)	C25—C24—H24	119.9
C22—P2—C16	105.16 (6)	C24—C25—C26	119.79 (14)
N5—P2—Fe1	99.62 (4)	C24—C25—H25	120.1
C22—P2—Fe1	118.48 (4)	C26—C25—H25	120.1
C16—P2—Fe1	121.60 (5)	C25—C26—C27	120.39 (14)
C2—O1—C34	118.51 (11)	C25—C26—H26	119.8
C1—N1—C3	115.24 (11)	C27—C26—H26	119.8
C1—N1—Fe1	122.07 (8)	C26—C27—C22	120.00 (13)
C3—N1—Fe1	122.69 (9)	C26—C27—H27	120.0
C2—N2—C1	114.05 (11)	C22—C27—H27	120.0
C3—N3—C2	114.42 (11)	N6—C28—C29	178.68 (15)
C1—N4—P1	118.59 (9)	C28—C29—H29A	109.5
C1—N4—H4N	120.7	C28—C29—H29B	109.5
P1—N4—H4N	120.7	H29A—C29—H29B	109.5
C3—N5—P2	118.55 (9)	C28—C29—H29C	109.5
C3—N5—H5N	120.7	H29A—C29—H29C	109.5
P2—N5—H5N	120.7	H29B—C29—H29C	109.5
C28—N6—Fe1	174.22 (12)	N7—C30—C31	179.24 (17)
C30—N7—Fe1	176.80 (12)	C30—C31—H31A	109.5
C32—N8—Fe1	179.27 (11)	C30—C31—H31B	109.5
N2—C1—N1	125.14 (11)	H31A—C31—H31B	109.5
N2—C1—N4	118.25 (11)	C30—C31—H31C	109.5
N1—C1—N4	116.59 (11)	H31A—C31—H31C	109.5
O1—C2—N2	119.85 (12)	H31B—C31—H31C	109.5
O1—C2—N3	113.21 (11)	N8—C32—C33	177.90 (16)
N2—C2—N3	126.93 (12)	C32—C33—H33A	109.5
N3—C3—N5	119.61 (11)	C32—C33—H33B	109.5
N3—C3—N1	124.04 (11)	H33A—C33—H33B	109.5
N5—C3—N1	116.35 (11)	C32—C33—H33C	109.5
C9—C4—C5	120.05 (13)	H33A—C33—H33C	109.5
C9—C4—P1	122.06 (11)	H33B—C33—H33C	109.5
C5—C4—P1	117.17 (10)	O1—C34—C35	110.26 (13)
C6—C5—C4	119.86 (14)	O1—C34—H34A	109.6
C6—C5—H5	120.1	C35—C34—H34A	109.6
C4—C5—H5	120.1	O1—C34—H34B	109.6
C5—C6—C7	119.87 (15)	C35—C34—H34B	109.6
C5—C6—H6	120.1	H34A—C34—H34B	108.1
C7—C6—H6	120.1	C34—C35—H35A	109.5
C8—C7—C6	120.41 (15)	C34—C35—H35B	109.5
C8—C7—H7	119.8	H35A—C35—H35B	109.5
C6—C7—H7	119.8	C34—C35—H35C	109.5
C7—C8—C9	120.08 (16)	H35A—C35—H35C	109.5
C7—C8—H8	120.0	H35B—C35—H35C	109.5
C9—C8—H8	120.0	F3—B1—F1	110.60 (15)
C4—C9—C8	119.74 (15)	F3—B1—F2	108.26 (14)
C4—C9—H9	120.1	F1—B1—F2	109.22 (14)
C8—C9—H9	120.1	F3—B1—F4	109.10 (13)
C11—C10—C15	119.56 (12)	F1—B1—F4	109.80 (13)
C11—C10—P1	121.28 (10)	F2—B1—F4	109.85 (14)
C15—C10—P1	119.15 (10)	F5—B2—F7	111.28 (17)
C10—C11—C12	120.02 (13)	F5—B2—F6	110.76 (15)
C10—C11—H11	120.0	F7—B2—F6	109.86 (15)
C12—C11—H11	120.0	F5—B2—F8	108.77 (14)
C13—C12—C11	120.11 (13)	F7—B2—F8	106.97 (14)
C13—C12—H12	119.9	F6—B2—F8	109.10 (16)
C11—C12—H12	119.9	N9—C36—C37	178.3 (2)
C12—C13—C14	120.25 (12)	C36—C37—H37A	109.5
C12—C13—H13	119.9	C36—C37—H37B	109.5
C14—C13—H13	119.9	H37A—C37—H37B	109.5
C15—C14—C13	119.90 (13)	C36—C37—H37C	109.5
C15—C14—H14	120.1	H37A—C37—H37C	109.5
C13—C14—H14	120.1	H37B—C37—H37C	109.5
C14—C15—C10	120.16 (13)	N10—C38—C39	179.6 (2)
C14—C15—H15	119.9	C38—C39—H39A	109.5
C10—C15—H15	119.9	C38—C39—H39B	109.5
C17—C16—C21	119.97 (13)	H39A—C39—H39B	109.5
C17—C16—P2	120.80 (11)	C38—C39—H39C	109.5
C21—C16—P2	119.21 (11)	H39A—C39—H39C	109.5
C16—C17—C18	119.50 (16)	H39B—C39—H39C	109.5
N7—Fe1—P1—N4	97.16 (5)	C1—N1—C3—N3	0.95 (18)
N8—Fe1—P1—N4	−82.94 (5)	Fe1—N1—C3—N3	−179.47 (9)
N6—Fe1—P1—N4	−174.91 (5)	C1—N1—C3—N5	−178.57 (11)
N1—Fe1—P1—N4	4.89 (5)	Fe1—N1—C3—N5	1.02 (16)
P2—Fe1—P1—N4	14.95 (7)	N4—P1—C4—C9	−21.11 (14)
N7—Fe1—P1—C4	−15.41 (6)	C10—P1—C4—C9	−130.97 (13)
N8—Fe1—P1—C4	164.49 (6)	Fe1—P1—C4—C9	87.77 (13)
N6—Fe1—P1—C4	72.52 (6)	N4—P1—C4—C5	168.62 (11)
N1—Fe1—P1—C4	−107.68 (6)	C10—P1—C4—C5	58.76 (12)
P2—Fe1—P1—C4	−97.62 (7)	Fe1—P1—C4—C5	−82.50 (11)
N7—Fe1—P1—C10	−146.23 (6)	C9—C4—C5—C6	0.3 (2)
N8—Fe1—P1—C10	33.66 (6)	P1—C4—C5—C6	170.76 (13)
N6—Fe1—P1—C10	−58.31 (6)	C4—C5—C6—C7	0.2 (3)
N1—Fe1—P1—C10	121.50 (6)	C5—C6—C7—C8	−0.1 (3)
P2—Fe1—P1—C10	131.56 (7)	C6—C7—C8—C9	−0.5 (3)
N7—Fe1—P2—N5	−90.44 (5)	C5—C4—C9—C8	−0.8 (3)
N8—Fe1—P2—N5	89.62 (5)	P1—C4—C9—C8	−170.83 (15)
N6—Fe1—P2—N5	−178.34 (5)	C7—C8—C9—C4	0.9 (3)
N1—Fe1—P2—N5	1.75 (5)	N4—P1—C10—C11	122.93 (11)
P1—Fe1—P2—N5	−8.32 (7)	C4—P1—C10—C11	−126.80 (11)
N7—Fe1—P2—C22	153.87 (6)	Fe1—P1—C10—C11	8.96 (13)
N8—Fe1—P2—C22	−26.08 (6)	N4—P1—C10—C15	−58.64 (12)
N6—Fe1—P2—C22	65.96 (6)	C4—P1—C10—C15	51.64 (12)
N1—Fe1—P2—C22	−113.95 (6)	Fe1—P1—C10—C15	−172.61 (9)
P1—Fe1—P2—C22	−124.01 (7)	C15—C10—C11—C12	1.0 (2)
N7—Fe1—P2—C16	20.79 (6)	P1—C10—C11—C12	179.40 (10)
N8—Fe1—P2—C16	−159.16 (6)	C10—C11—C12—C13	−1.3 (2)
N6—Fe1—P2—C16	−67.12 (6)	C11—C12—C13—C14	0.9 (2)
N1—Fe1—P2—C16	112.97 (6)	C12—C13—C14—C15	−0.2 (2)
P1—Fe1—P2—C16	102.91 (8)	C13—C14—C15—C10	−0.1 (2)
N7—Fe1—N1—C1	−93.16 (10)	C11—C10—C15—C14	−0.3 (2)
N8—Fe1—N1—C1	86.64 (10)	P1—C10—C15—C14	−178.74 (11)
P1—Fe1—N1—C1	−4.78 (9)	N5—P2—C16—C17	−140.20 (12)
P2—Fe1—N1—C1	177.74 (10)	C22—P2—C16—C17	−28.22 (13)
N7—Fe1—N1—C3	87.28 (10)	Fe1—P2—C16—C17	110.08 (11)
N8—Fe1—N1—C3	−92.93 (10)	N5—P2—C16—C21	41.53 (13)
P1—Fe1—N1—C3	175.66 (10)	C22—P2—C16—C21	153.51 (11)
P2—Fe1—N1—C3	−1.82 (9)	Fe1—P2—C16—C21	−68.19 (12)
C4—P1—N4—C1	114.59 (10)	C21—C16—C17—C18	−0.5 (2)
C10—P1—N4—C1	−137.37 (10)	P2—C16—C17—C18	−178.79 (12)
Fe1—P1—N4—C1	−5.76 (10)	C16—C17—C18—C19	−0.1 (2)
C22—P2—N5—C3	122.01 (10)	C17—C18—C19—C20	0.9 (3)
C16—P2—N5—C3	−127.55 (10)	C18—C19—C20—C21	−1.0 (3)
Fe1—P2—N5—C3	−1.97 (10)	C19—C20—C21—C16	0.3 (2)
C2—N2—C1—N1	−4.55 (18)	C17—C16—C21—C20	0.5 (2)
C2—N2—C1—N4	176.68 (11)	P2—C16—C21—C20	178.74 (12)
C3—N1—C1—N2	3.11 (18)	N5—P2—C22—C27	29.94 (13)
Fe1—N1—C1—N2	−176.49 (9)	C16—P2—C22—C27	−78.65 (12)
C3—N1—C1—N4	−178.10 (10)	Fe1—P2—C22—C27	141.48 (10)
Fe1—N1—C1—N4	2.30 (15)	N5—P2—C22—C23	−150.77 (11)
P1—N4—C1—N2	−178.03 (9)	C16—P2—C22—C23	100.64 (12)
P1—N4—C1—N1	3.10 (15)	Fe1—P2—C22—C23	−39.23 (13)
C34—O1—C2—N2	−0.48 (18)	C27—C22—C23—C24	0.8 (2)
C34—O1—C2—N3	178.84 (12)	P2—C22—C23—C24	−178.52 (12)
C1—N2—C2—O1	−178.51 (11)	C22—C23—C24—C25	−0.6 (2)
C1—N2—C2—N3	2.27 (19)	C23—C24—C25—C26	−0.1 (2)
C3—N3—C2—O1	−178.05 (11)	C24—C25—C26—C27	0.7 (2)
C3—N3—C2—N2	1.2 (2)	C25—C26—C27—C22	−0.5 (2)
C2—N3—C3—N5	176.61 (12)	C23—C22—C27—C26	−0.2 (2)
C2—N3—C3—N1	−2.89 (18)	P2—C22—C27—C26	179.05 (11)
P2—N5—C3—N3	−178.61 (9)	C2—O1—C34—C35	89.18 (17)
P2—N5—C3—N1	0.93 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···N9	0.88	2.03	2.892 (2)	168
N5—H5N···N3i	0.88	2.12	2.966 (2)	162
C9—H9···F7	0.95	2.53	3.276 (2)	135
C12—H12···F4	0.95	2.56	3.280 (2)	133
C13—H13···F2ii	0.95	2.54	3.464 (2)	164
C21—H21···F6	0.95	2.49	3.350 (2)	150
C25—H25···F5iii	0.95	2.42	3.365 (2)	174
C26—H26···F5i	0.95	2.50	3.144 (2)	125
C29—H29A···F3iv	0.98	2.35	3.239 (2)	151
C31—H31A···F8	0.98	2.46	3.360 (2)	153
C33—H33B···F4	0.98	2.49	3.191 (2)	128
C39—H39B···F2v	0.98	2.41	3.259 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4N⋯N9	0.88	2.03	2.892 (2)	168
N5—H5N⋯N3i	0.88	2.12	2.966 (2)	162
C9—H9⋯F7	0.95	2.53	3.276 (2)	135
C12—H12⋯F4	0.95	2.56	3.280 (2)	133
C13—H13⋯F2ii	0.95	2.54	3.464 (2)	164
C21—H21⋯F6	0.95	2.49	3.350 (2)	150
C25—H25⋯F5iii	0.95	2.42	3.365 (2)	174
C26—H26⋯F5i	0.95	2.50	3.144 (2)	125
C29—H29A⋯F3iv	0.98	2.35	3.239 (2)	151
C31—H31A⋯F8	0.98	2.46	3.360 (2)	153
C33—H33B⋯F4	0.98	2.49	3.191 (2)	128
C39—H39B⋯F2v	0.98	2.41	3.259 (3)	144

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .