Bis(2,9-dimethyl-1,10-phenanthroline)copper(I) penta-cyanido-nitro-soferrate(II).

The asymmetric unit of the title complex [Cu(C14H12N2)2]2[Fe(CN)5(NO)], consists of a [Cu(dmp)2](+) cation (dmp is 2,9-dimethyl-1,10-phenanthroline) and half an [Fe(CN)5(NO)](2-) anion. The anion is disordered across an inversion center with the Fe(II) ion slightly offset (ca 0.205Å) from the inversion center in the direction of the disordered trans-coordinating CN/NO ligands. The anion has a distorted octa-hedral coordination geometry. The Cu(I) ion is coordinated by two phenanthroline ligands in a distorted tetra-hedral geometry. The dihedral angle between the phenanthroline ligands is 77.16 (4) Å. In the crystal, the cations are connected to the anions by weak C-H⋯N hydrogen bonds. In addition, weak π-π stacking inter-actions are observed, with centroid-centroid distances in the range 3.512 (3)-3.859 (3) Å.

Related literature

For background to the direct synthesis of coordination compounds, see: Kokozay & Vassilyeva (2002 ▶); Nesterova et al. (2008 ▶). For the direct synthesis of heterometallic Cu-containing complexes, see: Buvaylo et al. (2005 ▶); Nesterova et al. (2004 ▶, 2005 ▶); Pryma et al. (2003 ▶). For the application of anionic complexes in the preparation of heterometallic compounds, see: Nikitina et al. (2008 ▶, 2009 ▶). For the structures of related complexes, see: Blake et al. (1998 ▶); Chen et al. (2002 ▶); Morpurgo et al. (1984 ▶); Cuttell et al. (2002 ▶); King et al. (2005 ▶); Soria et al. (2002 ▶); Shevyakova et al. (2002 ▶); Peresyp­kina & Vostrikova (2012 ▶).

Experimental

Crystal data

[Cu(C14H12N2)2]2[Fe(CN)5(NO)]

M = 1176.06

Triclinic,

a = 7.371 (3) Å

b = 13.741 (3) Å

c = 15.065 (4) Å

α = 115.269 (4)°

β = 95.327 (3)°

γ = 101.323 (4)°

V = 1325.9 (7) Å3

Z = 1

Mo Kα radiation

μ = 1.12 mm−1

T = 293 K

0.50 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur3 diffractometer

Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.604, T max = 0.807

8613 measured reflections

5112 independent reflections

3100 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.109

S = 0.93

5112 reflections

377 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813031760/lh5667sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031760/lh5667Isup2.hkl

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

[Cu(C14H12N2)2]2[Fe(CN)5(NO)]	Z = 1
Mr = 1176.06	F(000) = 604
Triclinic, P1	Dx = 1.473 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.371 (3) Å	Cell parameters from 4215 reflections
b = 13.741 (3) Å	θ = 2.7–24.8°
c = 15.065 (4) Å	µ = 1.12 mm−1
α = 115.269 (4)°	T = 293 K
β = 95.327 (3)°	Needle-shaped, red
γ = 101.323 (4)°	0.50 × 0.40 × 0.20 mm
V = 1325.9 (7) Å3

Oxford Diffraction Xcalibur3 diffractometer	5112 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3100 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 16.1827 pixels mm-1	θmax = 26.0°, θmin = 2.9°
ω–scans	h = −8→9
Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010)	k = −16→16
Tmin = 0.604, Tmax = 0.807	l = −18→15
8613 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0468P)2] where P = (Fo2 + 2Fc2)/3
5112 reflections	(Δ/σ)max = 0.001
377 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.31 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	Occ. (<1)
Cu1	0.24477 (7)	0.18237 (4)	0.30785 (3)	0.04709 (18)
Fe1	0.9747 (13)	0.5030 (13)	0.0033 (11)	0.0423 (14)	0.50
N1	0.3564 (4)	0.2540 (2)	0.2232 (2)	0.0377 (7)
N2	0.1731 (4)	0.0423 (2)	0.1741 (2)	0.0369 (7)
N3	0.3933 (4)	0.1682 (2)	0.4241 (2)	0.0379 (7)
N4	0.1040 (4)	0.2617 (2)	0.4159 (2)	0.0377 (7)
C1	0.4355 (5)	0.3608 (3)	0.2474 (3)	0.0464 (10)
C2	0.5081 (5)	0.3909 (3)	0.1771 (3)	0.0551 (11)
H2	0.5610	0.4656	0.1954	0.066*
C3	0.5025 (5)	0.3129 (4)	0.0833 (3)	0.0542 (11)
H3	0.5561	0.3335	0.0383	0.065*
C4	0.4148 (5)	0.2001 (3)	0.0542 (3)	0.0407 (9)
C5	0.3423 (4)	0.1751 (3)	0.1269 (3)	0.0345 (8)
C6	0.2450 (4)	0.0621 (3)	0.1008 (3)	0.0336 (8)
C7	0.2248 (5)	−0.0217 (3)	0.0027 (3)	0.0381 (9)
C8	0.3039 (5)	0.0072 (4)	−0.0683 (3)	0.0481 (10)
H8	0.2923	−0.0483	−0.1331	0.058*
C9	0.3950 (5)	0.1129 (4)	−0.0439 (3)	0.0492 (10)
H9	0.4457	0.1292	−0.0918	0.059*
C10	0.1271 (5)	−0.1296 (3)	−0.0187 (3)	0.0458 (10)
H10	0.1092	−0.1876	−0.0829	0.055*
C11	0.0583 (5)	−0.1498 (3)	0.0538 (3)	0.0460 (10)
H11	−0.0052	−0.2220	0.0394	0.055*
C12	0.0824 (5)	−0.0622 (3)	0.1510 (3)	0.0383 (9)
C13	0.4435 (6)	0.4460 (3)	0.3521 (3)	0.0654 (12)
H13A	0.5696	0.4934	0.3804	0.098*
H13B	0.4081	0.4091	0.3919	0.098*
H13C	0.3580	0.4902	0.3512	0.098*
C14	0.0096 (6)	−0.0831 (3)	0.2332 (3)	0.0559 (11)
H14A	0.0870	−0.1209	0.2545	0.084*
H14B	−0.1182	−0.1286	0.2086	0.084*
H14C	0.0137	−0.0133	0.2888	0.084*
C15	0.5321 (5)	0.1207 (3)	0.4270 (3)	0.0454 (10)
C16	0.6193 (6)	0.1264 (3)	0.5157 (3)	0.0547 (11)
H16	0.7197	0.0947	0.5157	0.066*
C17	0.5581 (6)	0.1786 (3)	0.6032 (3)	0.0549 (11)
H17	0.6176	0.1830	0.6625	0.066*
C18	0.4051 (5)	0.2251 (3)	0.6023 (3)	0.0451 (10)
C19	0.3273 (5)	0.2190 (3)	0.5108 (3)	0.0394 (9)
C20	0.1730 (5)	0.2687 (3)	0.5074 (3)	0.0358 (9)
C21	0.1046 (5)	0.3217 (3)	0.5935 (3)	0.0420 (9)
C22	0.1808 (6)	0.3230 (3)	0.6840 (3)	0.0528 (11)
H22	0.1298	0.3551	0.7405	0.063*
C23	0.3275 (6)	0.2779 (3)	0.6893 (3)	0.0548 (11)
H23	0.3780	0.2813	0.7498	0.066*
C24	−0.0412 (6)	0.3721 (3)	0.5857 (3)	0.0516 (11)
H24	−0.0922	0.4082	0.6412	0.062*
C25	−0.1066 (6)	0.3674 (3)	0.4963 (3)	0.0516 (10)
H25	−0.2005	0.4022	0.4912	0.062*
C26	−0.0338 (5)	0.3106 (3)	0.4117 (3)	0.0417 (9)
C27	0.5909 (6)	0.0609 (4)	0.3308 (3)	0.0619 (12)
H27A	0.5252	−0.0168	0.3005	0.093*
H27B	0.7245	0.0690	0.3432	0.093*
H27C	0.5611	0.0917	0.2866	0.093*
C28	−0.1065 (6)	0.3050 (4)	0.3126 (3)	0.0544 (11)
H28A	−0.0458	0.2601	0.2627	0.082*
H28B	−0.0798	0.3788	0.3182	0.082*
H28C	−0.2404	0.2723	0.2937	0.082*
C29	1.0149 (5)	0.4533 (3)	0.1060 (3)	0.0446 (9)
N5	1.0271 (5)	0.4286 (3)	0.1677 (3)	0.0631 (10)
C30	1.1809 (6)	0.6397 (3)	0.0926 (3)	0.0440 (9)
N6	1.2879 (5)	0.7213 (3)	0.1470 (3)	0.0626 (10)
C31	0.812 (5)	0.559 (2)	0.036 (2)	0.070 (5)	0.50
N7	0.681 (4)	0.603 (2)	0.0546 (17)	0.070 (5)	0.50
N8	0.805 (3)	0.5579 (11)	0.0446 (12)	0.026 (3)	0.50
O1	0.688 (3)	0.5921 (16)	0.0752 (11)	0.055 (3)	0.50

	U11	U22	U33	U12	U13	U23
Cu1	0.0659 (3)	0.0491 (3)	0.0278 (3)	0.0167 (2)	0.0157 (2)	0.0169 (2)
Fe1	0.057 (4)	0.0453 (14)	0.0274 (15)	0.012 (3)	0.009 (3)	0.0199 (12)
N1	0.0449 (17)	0.0362 (18)	0.0314 (17)	0.0069 (14)	0.0073 (14)	0.0166 (14)
N2	0.0400 (16)	0.0401 (18)	0.0323 (17)	0.0114 (14)	0.0067 (14)	0.0176 (14)
N3	0.0423 (16)	0.0398 (18)	0.0323 (17)	0.0120 (15)	0.0089 (15)	0.0162 (14)
N4	0.0433 (17)	0.0362 (17)	0.0302 (17)	0.0064 (14)	0.0041 (15)	0.0143 (14)
C1	0.047 (2)	0.045 (2)	0.045 (2)	0.0067 (19)	0.006 (2)	0.0210 (19)
C2	0.059 (2)	0.046 (3)	0.064 (3)	0.005 (2)	0.015 (2)	0.032 (2)
C3	0.056 (2)	0.065 (3)	0.053 (3)	0.009 (2)	0.019 (2)	0.038 (2)
C4	0.0384 (19)	0.057 (3)	0.034 (2)	0.0162 (19)	0.0086 (18)	0.0255 (19)
C5	0.0341 (18)	0.043 (2)	0.0300 (19)	0.0145 (17)	0.0068 (16)	0.0184 (17)
C6	0.0358 (18)	0.040 (2)	0.0295 (19)	0.0158 (17)	0.0084 (17)	0.0175 (16)
C7	0.0377 (19)	0.048 (2)	0.030 (2)	0.0209 (18)	0.0048 (17)	0.0153 (17)
C8	0.050 (2)	0.063 (3)	0.027 (2)	0.017 (2)	0.0100 (19)	0.0155 (19)
C9	0.046 (2)	0.080 (3)	0.031 (2)	0.022 (2)	0.0159 (19)	0.030 (2)
C10	0.047 (2)	0.048 (3)	0.036 (2)	0.020 (2)	0.0036 (19)	0.0117 (19)
C11	0.045 (2)	0.037 (2)	0.053 (3)	0.0118 (18)	0.004 (2)	0.017 (2)
C12	0.042 (2)	0.039 (2)	0.039 (2)	0.0130 (18)	0.0068 (18)	0.0210 (18)
C13	0.081 (3)	0.043 (3)	0.058 (3)	0.010 (2)	0.013 (3)	0.013 (2)
C14	0.067 (3)	0.048 (3)	0.061 (3)	0.015 (2)	0.022 (2)	0.031 (2)
C15	0.049 (2)	0.045 (2)	0.042 (2)	0.005 (2)	0.001 (2)	0.024 (2)
C16	0.054 (2)	0.055 (3)	0.058 (3)	0.017 (2)	0.003 (2)	0.029 (2)
C17	0.067 (3)	0.055 (3)	0.041 (3)	0.008 (2)	−0.005 (2)	0.027 (2)
C18	0.058 (2)	0.041 (2)	0.033 (2)	0.006 (2)	0.004 (2)	0.0179 (18)
C19	0.052 (2)	0.034 (2)	0.029 (2)	0.0044 (18)	0.0058 (18)	0.0152 (16)
C20	0.047 (2)	0.033 (2)	0.0260 (19)	0.0058 (17)	0.0075 (18)	0.0142 (16)
C21	0.053 (2)	0.039 (2)	0.031 (2)	0.0065 (19)	0.0102 (19)	0.0147 (17)
C22	0.072 (3)	0.054 (3)	0.026 (2)	0.009 (2)	0.014 (2)	0.0142 (19)
C23	0.080 (3)	0.053 (3)	0.026 (2)	0.009 (2)	0.006 (2)	0.0180 (19)
C24	0.064 (3)	0.050 (3)	0.035 (2)	0.013 (2)	0.022 (2)	0.0115 (19)
C25	0.058 (2)	0.050 (3)	0.050 (3)	0.023 (2)	0.017 (2)	0.020 (2)
C26	0.046 (2)	0.040 (2)	0.039 (2)	0.0096 (19)	0.0086 (19)	0.0193 (18)
C27	0.067 (3)	0.070 (3)	0.060 (3)	0.031 (2)	0.027 (2)	0.032 (2)
C28	0.062 (2)	0.065 (3)	0.041 (2)	0.024 (2)	0.009 (2)	0.026 (2)
C29	0.055 (2)	0.045 (2)	0.037 (2)	0.0171 (19)	0.015 (2)	0.0185 (19)
N5	0.093 (3)	0.067 (3)	0.044 (2)	0.028 (2)	0.020 (2)	0.0347 (19)
C30	0.058 (2)	0.048 (3)	0.033 (2)	0.021 (2)	0.009 (2)	0.0222 (19)
N6	0.069 (2)	0.062 (3)	0.052 (2)	0.016 (2)	−0.003 (2)	0.025 (2)
C31	0.087 (9)	0.109 (9)	0.050 (8)	0.044 (7)	0.017 (7)	0.061 (7)
N7	0.087 (9)	0.109 (9)	0.050 (8)	0.044 (7)	0.017 (7)	0.061 (7)
N8	0.039 (5)	0.022 (4)	0.011 (5)	0.012 (4)	0.009 (4)	−0.001 (4)
O1	0.082 (6)	0.087 (7)	0.027 (5)	0.057 (5)	0.026 (5)	0.036 (5)

Cu1—N2	2.034 (3)	C13—H13A	0.9600
Cu1—N4	2.039 (3)	C13—H13B	0.9600
Cu1—N1	2.053 (3)	C13—H13C	0.9600
Cu1—N3	2.079 (3)	C14—H14A	0.9600
Fe1—Fe1i	0.410 (15)	C14—H14B	0.9600
Fe1—C31	1.56 (4)	C14—H14C	0.9600
Fe1—N8	1.625 (19)	C15—C16	1.392 (5)
Fe1—C30i	1.908 (15)	C15—C27	1.484 (5)
Fe1—C31i	1.96 (4)	C16—C17	1.373 (6)
Fe1—C29	1.961 (16)	C16—H16	0.9300
Fe1—C29i	1.981 (16)	C17—C18	1.403 (5)
Fe1—C30	1.998 (15)	C17—H17	0.9300
Fe1—N8i	2.03 (2)	C18—C19	1.404 (5)
N1—C1	1.341 (4)	C18—C23	1.435 (5)
N1—C5	1.370 (4)	C19—C20	1.446 (5)
N2—C12	1.334 (4)	C20—C21	1.388 (5)
N2—C6	1.372 (4)	C21—C24	1.410 (5)
N3—C15	1.324 (5)	C21—C22	1.416 (5)
N3—C19	1.379 (4)	C22—C23	1.360 (6)
N4—C26	1.334 (4)	C22—H22	0.9300
N4—C20	1.380 (4)	C23—H23	0.9300
C1—C2	1.404 (5)	C24—C25	1.358 (5)
C1—C13	1.497 (5)	C24—H24	0.9300
C2—C3	1.351 (5)	C25—C26	1.401 (5)
C2—H2	0.9300	C25—H25	0.9300
C3—C4	1.409 (5)	C26—C28	1.502 (5)
C3—H3	0.9300	C27—H27A	0.9600
C4—C5	1.399 (5)	C27—H27B	0.9600
C4—C9	1.421 (5)	C27—H27C	0.9600
C5—C6	1.439 (5)	C28—H28A	0.9600
C6—C7	1.403 (5)	C28—H28B	0.9600
C7—C10	1.397 (5)	C28—H28C	0.9600
C7—C8	1.425 (5)	C29—N5	1.120 (4)
C8—C9	1.346 (5)	C29—Fe1i	1.981 (16)
C8—H8	0.9300	C30—N6	1.140 (5)
C9—H9	0.9300	C30—Fe1i	1.908 (15)
C10—C11	1.354 (5)	C31—N7	1.23 (5)
C10—H10	0.9300	C31—Fe1i	1.96 (4)
C11—C12	1.410 (5)	N8—O1	1.11 (3)
C11—H11	0.9300	N8—Fe1i	2.03 (2)
C12—C14	1.507 (5)
N2—Cu1—N4	135.31 (11)	C8—C9—H9	119.6
N2—Cu1—N1	82.52 (12)	C4—C9—H9	119.6
N4—Cu1—N1	121.22 (12)	C11—C10—C7	120.1 (4)
N2—Cu1—N3	114.85 (12)	C11—C10—H10	120.0
N4—Cu1—N3	82.49 (12)	C7—C10—H10	120.0
N1—Cu1—N3	126.67 (11)	C10—C11—C12	120.4 (4)
Fe1i—Fe1—C31	165 (5)	C10—C11—H11	119.8
Fe1i—Fe1—N8	166 (5)	C12—C11—H11	119.8
C31—Fe1—N8	4.6 (19)	N2—C12—C11	121.3 (3)
Fe1i—Fe1—C30i	97 (4)	N2—C12—C14	117.4 (3)
C31—Fe1—C30i	96.8 (11)	C11—C12—C14	121.3 (3)
N8—Fe1—C30i	96.8 (7)	C1—C13—H13A	109.5
Fe1i—Fe1—C31i	12 (4)	C1—C13—H13B	109.5
C31—Fe1—C31i	176.8 (10)	H13A—C13—H13B	109.5
N8—Fe1—C31i	175.8 (18)	C1—C13—H13C	109.5
C30i—Fe1—C31i	86.0 (10)	H13A—C13—H13C	109.5
Fe1i—Fe1—C29	87 (4)	H13B—C13—H13C	109.5
C31—Fe1—C29	99.8 (13)	C12—C14—H14A	109.5
N8—Fe1—C29	95.2 (10)	C12—C14—H14B	109.5
C30i—Fe1—C29	93.0 (7)	H14A—C14—H14B	109.5
C31i—Fe1—C29	81.6 (11)	C12—C14—H14C	109.5
Fe1i—Fe1—C29i	81 (4)	H14A—C14—H14C	109.5
C31—Fe1—C29i	91.8 (14)	H14B—C14—H14C	109.5
N8—Fe1—C29i	96.4 (10)	N3—C15—C16	121.8 (4)
C30i—Fe1—C29i	88.4 (6)	N3—C15—C27	116.8 (3)
C31i—Fe1—C29i	86.7 (11)	C16—C15—C27	121.3 (4)
C29—Fe1—C29i	168.1 (5)	C17—C16—C15	120.5 (4)
Fe1i—Fe1—C30	72 (4)	C17—C16—H16	119.8
C31—Fe1—C30	94.9 (12)	C15—C16—H16	119.8
N8—Fe1—C30	94.9 (9)	C16—C17—C18	119.5 (4)
C30i—Fe1—C30	168.2 (5)	C16—C17—H17	120.3
C31i—Fe1—C30	82.3 (9)	C18—C17—H17	120.3
C29—Fe1—C30	86.5 (6)	C17—C18—C19	117.0 (3)
C29i—Fe1—C30	89.7 (6)	C17—C18—C23	123.4 (4)
Fe1i—Fe1—N8i	11 (4)	C19—C18—C23	119.6 (4)
C31—Fe1—N8i	174.2 (19)	N3—C19—C18	122.7 (3)
N8—Fe1—N8i	177.2 (10)	N3—C19—C20	118.5 (3)
C30i—Fe1—N8i	85.9 (6)	C18—C19—C20	118.8 (3)
C31i—Fe1—N8i	3.6 (15)	N4—C20—C21	123.7 (3)
C29—Fe1—N8i	85.2 (8)	N4—C20—C19	116.3 (3)
C29i—Fe1—N8i	83.1 (7)	C21—C20—C19	120.1 (3)
C30—Fe1—N8i	82.4 (5)	C20—C21—C24	117.1 (4)
C1—N1—C5	118.1 (3)	C20—C21—C22	120.0 (4)
C1—N1—Cu1	130.8 (2)	C24—C21—C22	122.9 (4)
C5—N1—Cu1	111.1 (2)	C23—C22—C21	120.9 (4)
C12—N2—C6	118.1 (3)	C23—C22—H22	119.6
C12—N2—Cu1	130.3 (2)	C21—C22—H22	119.6
C6—N2—Cu1	111.5 (2)	C22—C23—C18	120.6 (4)
C15—N3—C19	118.5 (3)	C22—C23—H23	119.7
C15—N3—Cu1	131.4 (3)	C18—C23—H23	119.7
C19—N3—Cu1	110.1 (2)	C25—C24—C21	119.4 (4)
C26—N4—C20	117.4 (3)	C25—C24—H24	120.3
C26—N4—Cu1	130.0 (2)	C21—C24—H24	120.3
C20—N4—Cu1	112.6 (2)	C24—C25—C26	120.5 (4)
N1—C1—C2	121.0 (4)	C24—C25—H25	119.7
N1—C1—C13	117.3 (3)	C26—C25—H25	119.7
C2—C1—C13	121.7 (4)	N4—C26—C25	121.9 (4)
C3—C2—C1	121.1 (4)	N4—C26—C28	117.5 (3)
C3—C2—H2	119.5	C25—C26—C28	120.6 (4)
C1—C2—H2	119.5	C15—C27—H27A	109.5
C2—C3—C4	119.4 (4)	C15—C27—H27B	109.5
C2—C3—H3	120.3	H27A—C27—H27B	109.5
C4—C3—H3	120.3	C15—C27—H27C	109.5
C5—C4—C3	117.0 (3)	H27A—C27—H27C	109.5
C5—C4—C9	119.5 (4)	H27B—C27—H27C	109.5
C3—C4—C9	123.5 (4)	C26—C28—H28A	109.5
N1—C5—C4	123.2 (3)	C26—C28—H28B	109.5
N1—C5—C6	117.1 (3)	H28A—C28—H28B	109.5
C4—C5—C6	119.7 (3)	C26—C28—H28C	109.5
N2—C6—C7	123.2 (3)	H28A—C28—H28C	109.5
N2—C6—C5	117.4 (3)	H28B—C28—H28C	109.5
C7—C6—C5	119.4 (3)	N5—C29—Fe1	174.5 (4)
C10—C7—C6	116.9 (3)	N5—C29—Fe1i	173.2 (5)
C10—C7—C8	124.0 (3)	N6—C30—Fe1i	173.6 (4)
C6—C7—C8	119.0 (3)	N6—C30—Fe1	174.6 (4)
C9—C8—C7	121.6 (4)	N7—C31—Fe1	175 (3)
C9—C8—H8	119.2	N7—C31—Fe1i	173 (3)
C7—C8—H8	119.2	O1—N8—Fe1	176.5 (19)
C8—C9—C4	120.8 (4)	O1—N8—Fe1i	176.7 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N6ii	0.93	2.55	3.393 (6)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯N6i	0.93	2.55	3.393 (6)	151

Symmetry code: (i) .