Bis[chloridobis(1,10-phenanthroline)copper(II)] penta-cyanido-nitro-soferrate(II) di-methyl-formamide monosolvate.

The title complex [CuCl(C12H8N2)2]2[Fe(CN)5(NO)]·C3H7NO, consists of discrete [Cu(phen)2Cl](+) cations (phen is 1,10-phenanthroline), [Fe(CN)5NO](2-) anions and one di-methyl-formamide (DMF) solvent mol-ecule of crystallization per asymmetric unit. The Cu(II) atom is coordinated by two phenanthroline ligands and one chloride ion in a distorted trigonal-bipyramidal geometry. The dihedral angle between the phen ligands is 77.92 (7)°. The cation charge is balanced by a disordered nitro-prusside counter-anion with the Fe(II) atom located on an inversion center with a slightly distorted octa-hedral coordination geometry. In the crystal, weak C-H⋯N and C-H⋯Cl hydrogen bonds connect anions and cations into a two-dimensional network parallel to (100). In addition, π-π stacking inter-actions are observed with centroid-centroid distances in the range 3.565 (2)-3.760 (3)Å. The di-methyl-formamide solvent mol-ecule was refined as disordered about an inversion center.

Related literature

For background to the direct synthesis of coordination compounds, see: Buvaylo et al. (2005 ▶); Makhankova et al. (2002 ▶); Nesterova et al. (2004 ▶, 2005 ▶, 2008 ▶); Pryma et al. (2003 ▶); Vinogradova et al. (2002 ▶); Vassilyeva et al. (1997 ▶). For the structures of related complexes, see: Nikitina et al. (2008 ▶); Vreshch et al. (2009 ▶); Onawumi et al. (2010 ▶); Sui et al. (2006 ▶); Xiao et al. (2004 ▶); Soria et al. (2002 ▶); Shevyakova et al. (2002 ▶).

Experimental

Crystal data

[CuCl(C12H8N2)2]2[Fe(CN)5(NO)]·C3H7NO

M = 1207.85

Triclinic,

a = 9.9645 (13) Å

b = 10.6001 (18) Å

c = 12.623 (2) Å

α = 79.585 (14)°

β = 84.896 (12)°

γ = 82.047 (12)°

V = 1295.9 (4) Å3

Z = 1

Mo Kα radiation

μ = 1.25 mm−1

T = 293 K

0.50 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur 3 diffractometer

Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.575, T max = 0.789

11289 measured reflections

5647 independent reflections

2685 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.182

S = 0.99

5647 reflections

366 parameters

5 restraints

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.61 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 and PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813015547/lh5620sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015547/lh5620Isup2.hkl

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

[CuCl(C12H8N2)2]2[Fe(CN)5(NO)]·C3H7NO	V = 1295.9 (4) Å3
Mr = 1207.85	Z = 1
Triclinic, P1	F(000) = 614
Hall symbol: -P 1	Dx = 1.548 Mg m−3
a = 9.9645 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6001 (18) Å	µ = 1.25 mm−1
c = 12.623 (2) Å	T = 293 K
α = 79.585 (14)°	Block, green
β = 84.896 (12)°	0.50 × 0.40 × 0.20 mm
γ = 82.047 (12)°

Oxford Diffraction Xcalibur 3 diffractometer	5647 independent reflections
Radiation source: fine-focus sealed tube	2685 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 16.1827 pixels mm-1	θmax = 27.0°, θmin = 3.9°
ω–scans	h = −12→12
Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010)	k = −13→13
Tmin = 0.575, Tmax = 0.789	l = −16→16
11289 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.090P)2] where P = (Fo2 + 2Fc2)/3
5647 reflections	(Δ/σ)max = 0.001
366 parameters	Δρmax = 0.73 e Å−3
5 restraints	Δρmin = −0.61 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	0.17993 (5)	1.01179 (6)	0.25097 (5)	0.0663 (2)
Fe1	0.5000	0.5000	0.5000	0.0698 (3)
Cl1	0.04963 (14)	1.13793 (15)	0.12224 (12)	0.0907 (4)
N1	0.3265 (4)	1.1266 (4)	0.2215 (3)	0.0620 (9)
N2	0.3436 (4)	0.8814 (4)	0.1883 (3)	0.0672 (10)
N3	0.0513 (3)	0.8798 (4)	0.2939 (3)	0.0644 (10)
N4	0.2017 (3)	0.9736 (3)	0.4164 (3)	0.0567 (9)
C25	0.6109 (5)	0.4836 (4)	0.3720 (5)	0.0657 (12)
N5	0.6773 (4)	0.4748 (5)	0.2946 (4)	0.0842 (12)
C26	0.3406 (5)	0.5273 (5)	0.4171 (4)	0.0672 (12)
N6	0.2486 (4)	0.5418 (4)	0.3662 (4)	0.0821 (12)
C27	0.514 (4)	0.696 (3)	0.474 (4)	0.066 (6)	0.50
N7	0.5204 (17)	0.796 (3)	0.446 (3)	0.107 (9)	0.50
N7B	0.507 (3)	0.660 (2)	0.471 (3)	0.057 (5)	0.50
O7B	0.517 (2)	0.776 (2)	0.457 (2)	0.123 (8)	0.50
C1	0.3150 (5)	1.2477 (5)	0.2380 (4)	0.0752 (13)
H1	0.2321	1.2846	0.2654	0.090*
C2	0.4228 (6)	1.3221 (6)	0.2157 (4)	0.0824 (15)
H2	0.4134	1.4050	0.2323	0.099*
C3	0.5410 (6)	1.2716 (6)	0.1697 (4)	0.0872 (17)
H3	0.6121	1.3215	0.1520	0.105*
C4	0.5573 (4)	1.1453 (6)	0.1485 (4)	0.0694 (13)
C5	0.4460 (4)	1.0740 (5)	0.1772 (3)	0.0590 (11)
C6	0.4538 (4)	0.9441 (5)	0.1594 (3)	0.0605 (11)
C7	0.5754 (5)	0.8866 (6)	0.1118 (4)	0.0725 (14)
C8	0.5751 (7)	0.7591 (7)	0.0950 (4)	0.0942 (19)
H8	0.6514	0.7168	0.0625	0.113*
C9	0.4641 (7)	0.6979 (6)	0.1260 (5)	0.0972 (18)
H9	0.4648	0.6129	0.1163	0.117*
C10	0.3494 (6)	0.7617 (5)	0.1723 (4)	0.0829 (15)
H10	0.2737	0.7183	0.1928	0.100*
C11	0.6773 (5)	1.0833 (8)	0.1005 (4)	0.0872 (17)
H11	0.7523	1.1281	0.0820	0.105*
C12	0.6851 (5)	0.9618 (7)	0.0812 (4)	0.0874 (18)
H12	0.7640	0.9259	0.0471	0.105*
C13	−0.0238 (5)	0.8380 (5)	0.2298 (5)	0.0808 (15)
H13	−0.0229	0.8740	0.1569	0.097*
C14	−0.1058 (5)	0.7390 (5)	0.2707 (5)	0.0840 (15)
H14	−0.1585	0.7106	0.2246	0.101*
C15	−0.1078 (5)	0.6856 (5)	0.3758 (5)	0.0766 (14)
H15	−0.1617	0.6204	0.4027	0.092*
C16	−0.0292 (4)	0.7284 (4)	0.4436 (4)	0.0641 (12)
C17	0.0489 (4)	0.8265 (4)	0.3995 (4)	0.0600 (11)
C18	0.1300 (4)	0.8767 (4)	0.4657 (4)	0.0559 (10)
C19	0.1308 (4)	0.8260 (4)	0.5758 (4)	0.0611 (11)
C20	0.2095 (5)	0.8823 (5)	0.6371 (4)	0.0741 (13)
H20	0.2116	0.8539	0.7111	0.089*
C21	0.2825 (5)	0.9787 (5)	0.5879 (4)	0.0753 (13)
H21	0.3356	1.0154	0.6281	0.090*
C22	0.2776 (4)	1.0221 (5)	0.4772 (4)	0.0655 (12)
H22	0.3290	1.0872	0.4446	0.079*
C23	−0.0211 (5)	0.6775 (5)	0.5573 (4)	0.0723 (13)
H23	−0.0690	0.6091	0.5880	0.087*
C24	0.0522 (5)	0.7251 (5)	0.6187 (4)	0.0745 (14)
H24	0.0523	0.6916	0.6920	0.089*
N8	0.0000	0.5000	1.0000	0.157 (4)*
O1	−0.2091 (11)	0.465 (2)	1.004 (2)	0.273 (9)*	0.50
C28	−0.1053 (13)	0.483 (3)	0.9484 (13)	0.213 (10)*	0.50
H28A	−0.1030	0.4841	0.8688	0.256*	0.50
C29	0.015 (2)	0.504 (2)	1.1107 (9)	0.177 (8)*	0.50
H29A	−0.0724	0.4960	1.1561	0.212*	0.50
H29B	0.0843	0.4305	1.1378	0.212*	0.50
H29C	0.0475	0.5876	1.1150	0.212*	0.50
C30	0.1174 (18)	0.512 (2)	0.9282 (17)	0.186 (8)*	0.50
H30A	0.0824	0.5077	0.8573	0.223*	0.50
H30B	0.1544	0.5962	0.9235	0.223*	0.50
H30C	0.1912	0.4391	0.9462	0.223*	0.50

	U11	U22	U33	U12	U13	U23
Cu1	0.0579 (3)	0.0790 (4)	0.0627 (4)	−0.0218 (3)	0.0013 (3)	−0.0064 (3)
Fe1	0.0523 (5)	0.0874 (7)	0.0730 (7)	−0.0208 (5)	0.0005 (4)	−0.0155 (5)
Cl1	0.0809 (8)	0.1060 (11)	0.0834 (9)	−0.0154 (7)	−0.0016 (7)	−0.0103 (8)
N1	0.058 (2)	0.071 (3)	0.059 (2)	−0.0179 (18)	0.0037 (17)	−0.010 (2)
N2	0.066 (2)	0.077 (3)	0.053 (2)	−0.014 (2)	−0.0005 (18)	0.003 (2)
N3	0.057 (2)	0.072 (2)	0.065 (2)	−0.0181 (18)	−0.0070 (18)	−0.005 (2)
N4	0.0478 (17)	0.064 (2)	0.059 (2)	−0.0160 (16)	0.0040 (16)	−0.0101 (18)
C25	0.053 (2)	0.063 (3)	0.084 (3)	−0.010 (2)	−0.010 (2)	−0.016 (3)
N5	0.065 (2)	0.105 (3)	0.084 (3)	−0.012 (2)	0.001 (2)	−0.025 (3)
C26	0.057 (3)	0.063 (3)	0.077 (3)	−0.015 (2)	0.013 (2)	−0.003 (3)
N6	0.062 (2)	0.096 (3)	0.085 (3)	−0.021 (2)	−0.003 (2)	0.001 (3)
C27	0.072 (9)	0.048 (17)	0.091 (11)	−0.030 (11)	0.006 (7)	−0.033 (14)
N7	0.060 (7)	0.068 (14)	0.19 (2)	−0.003 (7)	−0.031 (10)	0.001 (11)
N7B	0.047 (5)	0.043 (12)	0.092 (8)	−0.016 (8)	−0.010 (5)	−0.028 (10)
O7B	0.186 (15)	0.047 (8)	0.140 (13)	−0.058 (8)	0.040 (10)	−0.017 (9)
C1	0.073 (3)	0.082 (4)	0.072 (3)	−0.020 (3)	0.009 (3)	−0.014 (3)
C2	0.094 (4)	0.086 (4)	0.073 (3)	−0.035 (3)	0.009 (3)	−0.019 (3)
C3	0.089 (4)	0.111 (5)	0.072 (3)	−0.058 (3)	−0.008 (3)	−0.009 (3)
C4	0.054 (2)	0.106 (4)	0.050 (3)	−0.021 (3)	−0.006 (2)	−0.005 (3)
C5	0.050 (2)	0.084 (3)	0.043 (2)	−0.021 (2)	−0.0032 (18)	−0.001 (2)
C6	0.063 (3)	0.076 (3)	0.040 (2)	−0.004 (2)	−0.009 (2)	−0.004 (2)
C7	0.065 (3)	0.096 (4)	0.051 (3)	0.006 (3)	−0.016 (2)	−0.003 (3)
C8	0.098 (4)	0.106 (5)	0.065 (3)	0.032 (4)	−0.010 (3)	−0.010 (3)
C9	0.132 (5)	0.075 (4)	0.075 (4)	0.007 (4)	−0.009 (4)	0.001 (3)
C10	0.109 (4)	0.071 (4)	0.066 (3)	−0.020 (3)	−0.003 (3)	−0.001 (3)
C11	0.053 (3)	0.152 (6)	0.059 (3)	−0.026 (3)	0.000 (2)	−0.014 (4)
C12	0.052 (3)	0.152 (6)	0.056 (3)	0.003 (3)	−0.008 (2)	−0.019 (4)
C13	0.070 (3)	0.100 (4)	0.079 (3)	−0.023 (3)	−0.015 (3)	−0.015 (3)
C14	0.075 (3)	0.091 (4)	0.096 (4)	−0.033 (3)	−0.015 (3)	−0.023 (3)
C15	0.056 (3)	0.071 (3)	0.104 (4)	−0.014 (2)	−0.007 (3)	−0.012 (3)
C16	0.045 (2)	0.059 (3)	0.087 (3)	−0.011 (2)	0.003 (2)	−0.010 (3)
C17	0.047 (2)	0.062 (3)	0.069 (3)	−0.0097 (19)	0.000 (2)	−0.007 (2)
C18	0.044 (2)	0.062 (3)	0.061 (3)	−0.0095 (19)	0.0022 (19)	−0.008 (2)
C19	0.052 (2)	0.067 (3)	0.061 (3)	−0.007 (2)	0.003 (2)	−0.004 (2)
C20	0.074 (3)	0.092 (4)	0.055 (3)	−0.013 (3)	−0.002 (2)	−0.010 (3)
C21	0.076 (3)	0.089 (4)	0.068 (3)	−0.021 (3)	−0.011 (3)	−0.020 (3)
C22	0.062 (2)	0.071 (3)	0.065 (3)	−0.018 (2)	−0.001 (2)	−0.007 (2)
C23	0.063 (3)	0.070 (3)	0.079 (3)	−0.020 (2)	0.009 (3)	0.003 (3)
C24	0.067 (3)	0.079 (3)	0.070 (3)	−0.014 (3)	0.009 (2)	0.004 (3)

Cu1—N1	1.996 (3)	C11—H11	0.9300
Cu1—N3	1.998 (4)	C12—H12	0.9300
Cu1—N4	2.079 (4)	C13—C14	1.415 (7)
Cu1—N2	2.177 (4)	C13—H13	0.9300
Cu1—Cl1	2.2855 (16)	C14—C15	1.345 (7)
Fe1—N7B	1.68 (2)	C14—H14	0.9300
Fe1—N7Bi	1.68 (2)	C15—C16	1.382 (7)
Fe1—C25i	1.895 (6)	C15—H15	0.9300
Fe1—C25	1.895 (6)	C16—C17	1.391 (6)
Fe1—C26i	1.939 (6)	C16—C23	1.444 (7)
Fe1—C26	1.939 (6)	C17—C18	1.427 (6)
Fe1—C27	2.07 (3)	C18—C19	1.397 (6)
Fe1—C27i	2.07 (3)	C19—C20	1.405 (7)
N1—C1	1.325 (6)	C19—C24	1.413 (6)
N1—C5	1.361 (5)	C20—C21	1.362 (7)
N2—C10	1.313 (6)	C20—H20	0.9300
N2—C6	1.351 (6)	C21—C22	1.393 (7)
N3—C13	1.320 (6)	C21—H21	0.9300
N3—C17	1.350 (6)	C22—H22	0.9300
N4—C22	1.334 (6)	C23—C24	1.317 (7)
N4—C18	1.358 (5)	C23—H23	0.9300
C25—N5	1.141 (6)	C24—H24	0.9300
C26—N6	1.143 (6)	N8—C28ii	1.333 (3)
C27—O7B	0.83 (4)	N8—C28	1.333 (3)
C27—N7	1.06 (4)	N8—C30ii	1.421 (9)
N7—N7B	1.45 (4)	N8—C30	1.421 (9)
N7B—O7B	1.23 (3)	N8—C29	1.426 (9)
C1—C2	1.398 (7)	N8—C29ii	1.426 (9)
C1—H1	0.9300	O1—C28	1.212 (3)
C2—C3	1.351 (8)	O1—C30ii	1.38 (3)
C2—H2	0.9300	C28—C29ii	1.13 (2)
C3—C4	1.397 (8)	C28—C30ii	1.56 (2)
C3—H3	0.9300	C28—H28A	1.0001
C4—C5	1.412 (6)	C29—C28ii	1.13 (2)
C4—C11	1.423 (8)	C29—C30ii	1.49 (2)
C5—C6	1.425 (7)	C29—H29A	1.0000
C6—C7	1.414 (6)	C29—H29B	0.9999
C7—C8	1.406 (8)	C29—H29C	1.0000
C7—C12	1.426 (8)	C30—O1ii	1.38 (3)
C8—C9	1.352 (8)	C30—C29ii	1.49 (2)
C8—H8	0.9300	C30—C28ii	1.56 (2)
C9—C10	1.383 (8)	C30—H30A	1.0000
C9—H9	0.9300	C30—H30B	1.0000
C10—H10	0.9300	C30—H30C	1.0000
C11—C12	1.344 (8)
N1—Cu1—N3	171.91 (15)	N3—C13—H13	119.6
N1—Cu1—N4	93.42 (14)	C14—C13—H13	119.6
N3—Cu1—N4	80.94 (14)	C15—C14—C13	120.3 (5)
N1—Cu1—N2	80.03 (16)	C15—C14—H14	119.8
N3—Cu1—N2	95.56 (15)	C13—C14—H14	119.8
N4—Cu1—N2	103.41 (14)	C14—C15—C16	119.4 (5)
N1—Cu1—Cl1	92.87 (12)	C14—C15—H15	120.3
N3—Cu1—Cl1	95.13 (11)	C16—C15—H15	120.3
N4—Cu1—Cl1	142.15 (10)	C15—C16—C17	118.0 (5)
N2—Cu1—Cl1	114.45 (11)	C15—C16—C23	124.6 (4)
N7B—Fe1—N7Bi	180.000 (3)	C17—C16—C23	117.4 (4)
N7B—Fe1—C25i	92.0 (13)	N3—C17—C16	122.6 (4)
N7Bi—Fe1—C25i	88.0 (13)	N3—C17—C18	116.7 (4)
N7B—Fe1—C25	88.0 (13)	C16—C17—C18	120.6 (4)
N7Bi—Fe1—C25	92.0 (13)	N4—C18—C19	123.8 (4)
C25i—Fe1—C25	180.000 (1)	N4—C18—C17	116.8 (4)
N7B—Fe1—C26i	91.7 (10)	C19—C18—C17	119.3 (4)
N7Bi—Fe1—C26i	88.3 (10)	C18—C19—C20	116.5 (4)
C25i—Fe1—C26i	89.34 (19)	C18—C19—C24	119.1 (4)
C25—Fe1—C26i	90.66 (19)	C20—C19—C24	124.4 (5)
N7B—Fe1—C26	88.3 (10)	C21—C20—C19	119.9 (5)
N7Bi—Fe1—C26	91.7 (10)	C21—C20—H20	120.1
C25i—Fe1—C26	90.66 (19)	C19—C20—H20	120.1
C25—Fe1—C26	89.34 (19)	C20—C21—C22	119.8 (5)
C26i—Fe1—C26	180.000 (1)	C20—C21—H21	120.1
N7B—Fe1—C27	4 (2)	C22—C21—H21	120.1
N7Bi—Fe1—C27	176 (2)	N4—C22—C21	122.2 (4)
C25i—Fe1—C27	89.7 (13)	N4—C22—H22	118.9
C25—Fe1—C27	90.3 (13)	C21—C22—H22	118.9
C26i—Fe1—C27	88.5 (12)	C24—C23—C16	121.9 (4)
C26—Fe1—C27	91.5 (12)	C24—C23—H23	119.1
N7B—Fe1—C27i	176 (2)	C16—C23—H23	119.1
N7Bi—Fe1—C27i	4 (2)	C23—C24—C19	121.6 (5)
C25i—Fe1—C27i	90.3 (13)	C23—C24—H24	119.2
C25—Fe1—C27i	89.7 (13)	C19—C24—H24	119.2
C26i—Fe1—C27i	91.5 (12)	C28ii—N8—C28	180.000 (4)
C26—Fe1—C27i	88.5 (12)	C28ii—N8—C30ii	111.0 (11)
C27—Fe1—C27i	180.000 (4)	C28—N8—C30ii	69.0 (11)
C1—N1—C5	118.9 (4)	C28ii—N8—C30	69.0 (11)
C1—N1—Cu1	125.8 (3)	C28—N8—C30	111.0 (11)
C5—N1—Cu1	115.3 (3)	C30ii—N8—C30	180.000 (5)
C10—N2—C6	118.9 (4)	C28ii—N8—C29	48.1 (10)
C10—N2—Cu1	131.9 (4)	C28—N8—C29	131.9 (10)
C6—N2—Cu1	109.2 (3)	C30ii—N8—C29	62.9 (11)
C13—N3—C17	118.9 (4)	C30—N8—C29	117.1 (11)
C13—N3—Cu1	126.9 (4)	C28ii—N8—C29ii	131.9 (10)
C17—N3—Cu1	114.1 (3)	C28—N8—C29ii	48.1 (10)
C22—N4—C18	117.7 (4)	C30ii—N8—C29ii	117.1 (11)
C22—N4—Cu1	131.1 (3)	C30—N8—C29ii	62.9 (11)
C18—N4—Cu1	111.1 (3)	C29—N8—C29ii	180.000 (7)
N5—C25—Fe1	179.4 (5)	C28—O1—C30ii	73.7 (8)
N6—C26—Fe1	178.2 (5)	C29ii—C28—O1	173.4 (12)
O7B—C27—N7	4 (3)	C29ii—C28—N8	70.3 (7)
O7B—C27—Fe1	174 (5)	O1—C28—N8	116.3 (9)
N7—C27—Fe1	170 (4)	C29ii—C28—C30ii	128.3 (8)
C27—N7—N7B	7 (4)	O1—C28—C30ii	58.2 (9)
O7B—N7B—N7	4 (2)	N8—C28—C30ii	58.1 (7)
O7B—N7B—Fe1	175 (3)	C29ii—C28—H28A	53.9
N7—N7B—Fe1	177 (2)	O1—C28—H28A	119.6
C27—O7B—N7B	7 (5)	N8—C28—H28A	124.1
N1—C1—C2	122.5 (5)	C30ii—C28—H28A	175.9
N1—C1—H1	118.7	C28ii—C29—N8	61.6 (6)
C2—C1—H1	118.7	C28ii—C29—C30ii	120.0 (10)
C3—C2—C1	118.9 (5)	N8—C29—C30ii	58.4 (7)
C3—C2—H2	120.5	C28ii—C29—H29A	173.5
C1—C2—H2	120.5	N8—C29—H29A	112.6
C2—C3—C4	120.7 (5)	C30ii—C29—H29A	54.2
C2—C3—H3	119.7	C28ii—C29—H29B	76.0
C4—C3—H3	119.7	N8—C29—H29B	107.6
C3—C4—C5	117.3 (4)	C30ii—C29—H29B	124.3
C3—C4—C11	125.0 (5)	H29A—C29—H29B	109.5
C5—C4—C11	117.7 (5)	C28ii—C29—H29C	71.1
N1—C5—C4	121.6 (4)	N8—C29—H29C	108.2
N1—C5—C6	117.2 (4)	C30ii—C29—H29C	126.2
C4—C5—C6	121.2 (4)	H29A—C29—H29C	109.5
N2—C6—C7	122.8 (5)	H29B—C29—H29C	109.5
N2—C6—C5	118.2 (4)	O1ii—C30—N8	100.9 (13)
C7—C6—C5	119.0 (4)	O1ii—C30—C29ii	159.1 (13)
C8—C7—C6	115.9 (5)	N8—C30—C29ii	58.7 (7)
C8—C7—C12	125.3 (5)	O1ii—C30—C28ii	48.1 (8)
C6—C7—C12	118.7 (5)	N8—C30—C28ii	52.8 (6)
C9—C8—C7	120.1 (5)	C29ii—C30—C28ii	111.5 (8)
C9—C8—H8	119.9	O1ii—C30—H30A	156.1
C7—C8—H8	119.9	N8—C30—H30A	102.4
C8—C9—C10	120.1 (6)	C29ii—C30—H30A	43.6
C8—C9—H9	120.0	C28ii—C30—H30A	155.1
C10—C9—H9	120.0	O1ii—C30—H30B	55.3
N2—C10—C9	122.2 (5)	N8—C30—H30B	113.5
N2—C10—H10	118.9	C29ii—C30—H30B	125.5
C9—C10—H10	118.9	C28ii—C30—H30B	82.6
C12—C11—C4	121.8 (5)	H30A—C30—H30B	109.5
C12—C11—H11	119.1	O1ii—C30—H30C	65.8
C4—C11—H11	119.1	N8—C30—H30C	112.3
C11—C12—C7	121.6 (5)	C29ii—C30—H30C	123.5
C11—C12—H12	119.2	C28ii—C30—H30C	85.5
C7—C12—H12	119.2	H30A—C30—H30C	109.5
N3—C13—C14	120.7 (5)	H30B—C30—H30C	109.5
N4—Cu1—N1—C1	−77.5 (4)	C17—N3—C13—C14	0.0 (7)
N2—Cu1—N1—C1	179.5 (4)	Cu1—N3—C13—C14	176.8 (4)
Cl1—Cu1—N1—C1	65.2 (4)	N3—C13—C14—C15	−0.2 (8)
N4—Cu1—N1—C5	104.9 (3)	C13—C14—C15—C16	0.1 (8)
N2—Cu1—N1—C5	1.8 (3)	C14—C15—C16—C17	0.3 (7)
Cl1—Cu1—N1—C5	−112.5 (3)	C14—C15—C16—C23	−178.9 (5)
N1—Cu1—N2—C10	−179.7 (5)	C13—N3—C17—C16	0.4 (7)
N3—Cu1—N2—C10	7.2 (5)	Cu1—N3—C17—C16	−176.8 (3)
N4—Cu1—N2—C10	89.2 (5)	C13—N3—C17—C18	−178.9 (4)
Cl1—Cu1—N2—C10	−91.0 (5)	Cu1—N3—C17—C18	3.9 (5)
N1—Cu1—N2—C6	−2.1 (3)	C15—C16—C17—N3	−0.5 (7)
N3—Cu1—N2—C6	−175.2 (3)	C23—C16—C17—N3	178.8 (4)
N4—Cu1—N2—C6	−93.2 (3)	C15—C16—C17—C18	178.7 (4)
Cl1—Cu1—N2—C6	86.6 (3)	C23—C16—C17—C18	−2.0 (6)
N4—Cu1—N3—C13	178.4 (4)	C22—N4—C18—C19	0.4 (6)
N2—Cu1—N3—C13	−78.8 (4)	Cu1—N4—C18—C19	176.7 (3)
Cl1—Cu1—N3—C13	36.4 (4)	C22—N4—C18—C17	179.7 (4)
N4—Cu1—N3—C17	−4.6 (3)	Cu1—N4—C18—C17	−3.9 (4)
N2—Cu1—N3—C17	98.1 (3)	N3—C17—C18—N4	0.2 (6)
Cl1—Cu1—N3—C17	−146.6 (3)	C16—C17—C18—N4	−179.1 (4)
N1—Cu1—N4—C22	6.1 (4)	N3—C17—C18—C19	179.6 (4)
N3—Cu1—N4—C22	−179.7 (4)	C16—C17—C18—C19	0.3 (6)
N2—Cu1—N4—C22	86.7 (4)	N4—C18—C19—C20	1.2 (6)
Cl1—Cu1—N4—C22	−93.0 (4)	C17—C18—C19—C20	−178.1 (4)
N1—Cu1—N4—C18	−169.6 (3)	N4—C18—C19—C24	180.0 (4)
N3—Cu1—N4—C18	4.6 (3)	C17—C18—C19—C24	0.7 (6)
N2—Cu1—N4—C18	−89.0 (3)	C18—C19—C20—C21	−1.8 (7)
Cl1—Cu1—N4—C18	91.3 (3)	C24—C19—C20—C21	179.5 (4)
C5—N1—C1—C2	−2.7 (7)	C19—C20—C21—C22	0.8 (8)
Cu1—N1—C1—C2	179.7 (4)	C18—N4—C22—C21	−1.5 (7)
N1—C1—C2—C3	4.0 (8)	Cu1—N4—C22—C21	−176.9 (3)
C1—C2—C3—C4	−2.5 (8)	C20—C21—C22—N4	0.9 (8)
C2—C3—C4—C5	0.0 (8)	C15—C16—C23—C24	−177.7 (5)
C2—C3—C4—C11	−180.0 (5)	C17—C16—C23—C24	3.0 (7)
C1—N1—C5—C4	0.0 (6)	C16—C23—C24—C19	−2.2 (8)
Cu1—N1—C5—C4	177.8 (3)	C18—C19—C24—C23	0.3 (7)
C1—N1—C5—C6	−179.2 (4)	C20—C19—C24—C23	179.0 (5)
Cu1—N1—C5—C6	−1.4 (5)	C30ii—O1—C28—N8	3 (2)
C3—C4—C5—N1	1.4 (6)	C30ii—N8—C28—C29ii	178 (3)
C11—C4—C5—N1	−178.7 (4)	C30—N8—C28—C29ii	−2 (3)
C3—C4—C5—C6	−179.5 (4)	C29—N8—C28—C29ii	180.000 (3)
C11—C4—C5—C6	0.4 (6)	C28ii—N8—C28—O1	171 (100)
C10—N2—C6—C7	0.5 (7)	C30ii—N8—C28—O1	−3 (2)
Cu1—N2—C6—C7	−177.5 (3)	C30—N8—C28—O1	177 (2)
C10—N2—C6—C5	180.0 (4)	C29—N8—C28—O1	−1 (4)
Cu1—N2—C6—C5	2.0 (5)	C29ii—N8—C28—O1	179 (4)
N1—C5—C6—N2	−0.6 (6)	C30—N8—C28—C30ii	180.000 (5)
C4—C5—C6—N2	−179.8 (4)	C29—N8—C28—C30ii	2 (3)
N1—C5—C6—C7	178.9 (4)	C29ii—N8—C28—C30ii	−178 (3)
C4—C5—C6—C7	−0.2 (6)	C28—N8—C29—C28ii	180.000 (4)
N2—C6—C7—C8	0.5 (7)	C30ii—N8—C29—C28ii	−177 (3)
C5—C6—C7—C8	−179.0 (4)	C30—N8—C29—C28ii	3 (3)
N2—C6—C7—C12	178.2 (4)	C28ii—N8—C29—C30ii	177 (3)
C5—C6—C7—C12	−1.3 (6)	C28—N8—C29—C30ii	−3 (3)
C6—C7—C8—C9	−1.5 (8)	C30—N8—C29—C30ii	180.000 (4)
C12—C7—C8—C9	−179.0 (5)	C28ii—N8—C30—O1ii	−2.8 (19)
C7—C8—C9—C10	1.4 (9)	C28—N8—C30—O1ii	177.2 (19)
C6—N2—C10—C9	−0.6 (8)	C29—N8—C30—O1ii	−5 (2)
Cu1—N2—C10—C9	176.9 (4)	C29ii—N8—C30—O1ii	175 (2)
C8—C9—C10—N2	−0.4 (9)	C28ii—N8—C30—C29ii	−178 (2)
C3—C4—C11—C12	−179.1 (5)	C28—N8—C30—C29ii	2 (2)
C5—C4—C11—C12	1.0 (7)	C29—N8—C30—C29ii	180.000 (4)
C4—C11—C12—C7	−2.6 (8)	C28—N8—C30—C28ii	180.000 (4)
C8—C7—C12—C11	−179.8 (5)	C29—N8—C30—C28ii	−2 (2)
C6—C7—C12—C11	2.7 (7)	C29ii—N8—C30—C28ii	178 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl1iii	0.93	2.82	3.701 (6)	159
C23—H23···N6iv	0.93	2.52	3.425 (7)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cl1i	0.93	2.82	3.701 (6)	159
C23—H23⋯N6ii	0.93	2.52	3.425 (7)	163

Symmetry codes: (i) ; (ii) .