[N,N,N',N'-Tetra-kis(benzimidazol-2-ylmeth-yl)cyclo-hexane-1,2-trans-diamine]-iron(II) bis-(perchlorate) methanol solvate.

In the title compound, [Fe(C(38)H(38)N(10))](ClO(4))(2)·CH(3)OH, the Fe(II) atom has a distorted octa-hedral coordination environment with four benzimidazol N atoms and two amino N atoms from an N,N,N',N'-tetra-kis-(benzimidazol-2-ylmeth-yl)cyclo-hexane-1,2-trans-diamine ligand. The uncoordinated solvent methanol mol-ecule is hydrogen bonded to an O atom of a perchlorate anion. One of the perchlorate anions is disordered over two sets of sites with occupancy factors of 0.539 (14) and 0.461 (14). N-H⋯O and C-H⋯O hydrogen bonds, as well as π-π stacking inter-actions between the imidazol rings and between the imidazol and benzene rings [centroid-centroid distances = 3.714 (2) and 3.705 (2) Å] give rise to a three-dimensional network.

Related literature

For model systems containing pyrazole chelates and related groups, see: Main (1992 ▶). For iron complexes with N,N,N′,N′-tetra­kis­(2-benzimidazolylmeth­yl)cyclo­hexane-1,2-trans-diamine, see: Mei et al. (2010 ▶); Zhao et al. (2005 ▶). For the synthesis of the ligand, see: Hendriks et al. (1982 ▶).

Experimental

Crystal data

[Fe(C38H38N10)](ClO4)2·CH4O

M = 921.58

Monoclinic,

a = 14.3867 (6) Å

b = 15.9145 (6) Å

c = 18.8218 (8) Å

β = 103.175 (1)°

V = 4196.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.55 mm−1

T = 298 K

0.30 × 0.16 × 0.10 mm

Data collection

Bruker APEX CCD diffractometer

21311 measured reflections

7369 independent reflections

5765 reflections with I > 2σ(I)

R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.176

S = 1.07

7369 reflections

612 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.53 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011810/hy2418sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011810/hy2418Isup2.hkl

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

[Fe(C38H38N10)](ClO4)2·CH4O	F(000) = 1912
Mr = 921.58	Dx = 1.459 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8487 reflections
a = 14.3867 (6) Å	θ = 2.4–28.0°
b = 15.9145 (6) Å	µ = 0.55 mm−1
c = 18.8218 (8) Å	T = 298 K
β = 103.175 (1)°	Block, colorless
V = 4196.0 (3) Å3	0.30 × 0.16 × 0.10 mm
Z = 4

Bruker APEX CCD diffractometer	5765 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.083
graphite	θmax = 25.0°, θmin = 2.0°
φ and ω scans	h = −15→17
21311 measured reflections	k = −17→18
7369 independent reflections	l = −22→22

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.1022P)2 + 2.0578P] where P = (Fo2 + 2Fc2)/3
7369 reflections	(Δ/σ)max < 0.001
612 parameters	Δρmax = 0.57 e Å−3
10 restraints	Δρmin = −0.53 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.49217 (3)	0.51266 (3)	0.25944 (3)	0.03221 (18)
N1	0.40904 (18)	0.63557 (16)	0.22008 (16)	0.0340 (6)
N2	0.59753 (19)	0.61865 (17)	0.31077 (17)	0.0367 (7)
N3	0.5240 (2)	0.53017 (17)	0.15388 (17)	0.0387 (7)
N4	0.5194 (2)	0.61519 (17)	0.06081 (16)	0.0378 (7)
H4A	0.5027	0.6569	0.0317	0.045*
N5	0.35367 (19)	0.46902 (17)	0.21018 (16)	0.0357 (6)
N6	0.2082 (2)	0.50488 (18)	0.15204 (17)	0.0399 (7)
H6A	0.1577	0.5350	0.1380	0.048*
N7	0.62225 (19)	0.45068 (17)	0.29869 (16)	0.0370 (7)
N8	0.7795 (2)	0.4561 (2)	0.33400 (18)	0.0455 (8)
H8A	0.8364	0.4764	0.3434	0.055*
N9	0.4597 (2)	0.52468 (17)	0.36472 (17)	0.0389 (7)
N10	0.4732 (2)	0.60837 (17)	0.45995 (16)	0.0418 (7)
H10A	0.4973	0.6451	0.4925	0.050*
C1	0.4544 (2)	0.7063 (2)	0.2673 (2)	0.0377 (8)
H1A	0.4429	0.6957	0.3159	0.045*
C2	0.4124 (3)	0.7932 (2)	0.2440 (3)	0.0510 (10)
H2A	0.348 (3)	0.795 (3)	0.251 (3)	0.066 (13)*
H2B	0.407 (3)	0.800 (3)	0.196 (3)	0.061 (14)*
C3	0.4708 (3)	0.8639 (2)	0.2853 (3)	0.0591 (11)
H3A	0.4433	0.9174	0.2666	0.071*
H3B	0.4694	0.8605	0.3365	0.071*
C4	0.5723 (3)	0.8592 (2)	0.2776 (3)	0.0580 (11)
H4B	0.6082	0.9065	0.3024	0.070*
H4C	0.5739	0.8622	0.2264	0.070*
C5	0.6177 (3)	0.7774 (2)	0.3101 (3)	0.0535 (10)
H5A	0.6826	0.7746	0.3037	0.064*
H5B	0.6203	0.7770	0.3620	0.064*
C6	0.5629 (2)	0.7006 (2)	0.2751 (2)	0.0379 (8)
H6B	0.5729	0.6976	0.2254	0.045*
C7	0.4096 (3)	0.6477 (2)	0.1418 (2)	0.0396 (8)
H7A	0.350 (2)	0.6305 (19)	0.1137 (19)	0.040 (10)*
H7B	0.416 (2)	0.705 (2)	0.131 (2)	0.040 (10)*
C8	0.4854 (2)	0.5975 (2)	0.11997 (19)	0.0349 (7)
C9	0.5883 (2)	0.5004 (2)	0.1148 (2)	0.0389 (8)
C10	0.6475 (3)	0.4303 (2)	0.1245 (2)	0.0509 (10)
H10B	0.6492	0.3930	0.1628	0.061*
C11	0.7036 (3)	0.4184 (3)	0.0751 (2)	0.0577 (11)
H11A	0.7429	0.3714	0.0797	0.069*
C12	0.7031 (3)	0.4747 (3)	0.0187 (2)	0.0533 (10)
H12A	0.7443	0.4656	−0.0121	0.064*
C13	0.6443 (3)	0.5431 (2)	0.0068 (2)	0.0466 (9)
H13A	0.6437	0.5801	−0.0316	0.056*
C14	0.5858 (2)	0.5544 (2)	0.0551 (2)	0.0366 (8)
C15	0.3110 (2)	0.6161 (2)	0.2272 (2)	0.0386 (8)
H15A	0.2659	0.6559	0.1994	0.046*
H15B	0.3071	0.6187	0.2779	0.046*
C16	0.2893 (2)	0.5288 (2)	0.1979 (2)	0.0369 (8)
C17	0.3114 (2)	0.4004 (2)	0.1689 (2)	0.0385 (8)
C18	0.3487 (3)	0.3210 (2)	0.1593 (2)	0.0522 (10)
H18A	0.4093	0.3049	0.1848	0.063*
C19	0.2916 (3)	0.2680 (3)	0.1104 (3)	0.0653 (12)
H19A	0.3138	0.2146	0.1028	0.078*
C20	0.2023 (3)	0.2922 (3)	0.0723 (3)	0.0657 (13)
H20A	0.1666	0.2550	0.0388	0.079*
C21	0.1638 (3)	0.3692 (3)	0.0818 (2)	0.0561 (11)
H21A	0.1030	0.3845	0.0562	0.067*
C22	0.2201 (2)	0.4226 (2)	0.1312 (2)	0.0427 (9)
C23	0.6903 (2)	0.5920 (2)	0.2965 (2)	0.0427 (8)
H23A	0.7424	0.6207	0.3293	0.051*
H23B	0.6928	0.6053	0.2467	0.051*
C24	0.6979 (2)	0.4993 (2)	0.3088 (2)	0.0398 (8)
C25	0.6562 (3)	0.3702 (2)	0.3196 (2)	0.0391 (8)
C26	0.6065 (3)	0.2960 (2)	0.3245 (2)	0.0521 (10)
H26A	0.5403	0.2936	0.3102	0.063*
C27	0.6593 (3)	0.2266 (3)	0.3514 (3)	0.0649 (12)
H27A	0.6284	0.1760	0.3549	0.078*
C28	0.7582 (4)	0.2303 (3)	0.3735 (3)	0.0711 (14)
H28A	0.7916	0.1822	0.3923	0.085*
C29	0.8079 (3)	0.3027 (3)	0.3685 (3)	0.0607 (12)
H29A	0.8741	0.3045	0.3824	0.073*
C30	0.7551 (3)	0.3730 (2)	0.3420 (2)	0.0438 (9)
C31	0.6018 (2)	0.6166 (2)	0.3898 (2)	0.0409 (8)
H31A	0.6125	0.6730	0.4096	0.049*
H31B	0.6549	0.5817	0.4140	0.049*
C32	0.5113 (2)	0.5826 (2)	0.4044 (2)	0.0379 (8)
C33	0.3809 (3)	0.5110 (2)	0.3957 (2)	0.0398 (8)
C34	0.3042 (3)	0.4574 (3)	0.3759 (2)	0.0539 (10)
H34A	0.2993	0.4199	0.3374	0.065*
C35	0.2348 (3)	0.4618 (3)	0.4160 (3)	0.0653 (12)
H35A	0.1823	0.4261	0.4043	0.078*
C36	0.2417 (3)	0.5179 (3)	0.4731 (3)	0.0636 (12)
H36A	0.1923	0.5203	0.4975	0.076*
C37	0.3185 (3)	0.5701 (3)	0.4948 (2)	0.0542 (10)
H37A	0.3234	0.6067	0.5340	0.065*
C38	0.3891 (3)	0.5654 (2)	0.4551 (2)	0.0407 (8)
Cl1	0.55488 (10)	0.17228 (8)	0.01931 (8)	0.0758 (4)
O1	0.5176 (5)	0.2430 (3)	0.0429 (3)	0.141 (2)
O2	0.6396 (4)	0.1476 (4)	0.0605 (3)	0.153 (2)
O3	0.4884 (4)	0.1073 (3)	0.0204 (3)	0.155 (2)
O4	0.5571 (4)	0.1862 (3)	−0.0548 (3)	0.1265 (18)
Cl2	0.4081 (5)	0.1971 (4)	0.4315 (5)	0.064 (2)	0.461 (14)
O5	0.3219 (10)	0.1788 (13)	0.4499 (11)	0.124 (7)	0.461 (14)
O6	0.4447 (13)	0.1189 (8)	0.4236 (10)	0.113 (7)	0.461 (14)
O7	0.3795 (11)	0.2458 (9)	0.3656 (7)	0.164 (7)	0.461 (14)
O8	0.4841 (6)	0.2349 (7)	0.4747 (8)	0.107 (6)	0.461 (14)
Cl2'	0.4056 (7)	0.1978 (6)	0.4416 (6)	0.088 (3)	0.539 (14)
O5'	0.3123 (10)	0.2126 (13)	0.4188 (11)	0.132 (6)	0.539 (14)
O6'	0.4301 (11)	0.1350 (10)	0.3880 (10)	0.111 (6)	0.539 (14)
O7'	0.4525 (10)	0.2711 (7)	0.4260 (7)	0.119 (5)	0.539 (14)
O8'	0.4341 (9)	0.1893 (8)	0.5185 (5)	0.132 (5)	0.539 (14)
O1S	0.9648 (3)	0.5167 (3)	0.3479 (3)	0.0902 (12)
H1S	0.9747	0.5408	0.3956	0.135*
C1S	0.9867 (6)	0.5786 (5)	0.3004 (5)	0.137 (3)
H1SA	1.0452	0.5637	0.2872	0.205*
H1SB	0.9942	0.6323	0.3242	0.205*
H1SC	0.9367	0.5828	0.2570	0.205*

	U11	U22	U33	U12	U13	U23
Fe1	0.0279 (3)	0.0359 (3)	0.0307 (3)	0.00317 (18)	0.0022 (2)	0.00087 (19)
N1	0.0307 (14)	0.0382 (14)	0.0321 (16)	0.0003 (11)	0.0053 (12)	−0.0031 (12)
N2	0.0301 (14)	0.0376 (14)	0.0403 (18)	0.0020 (11)	0.0034 (13)	0.0022 (13)
N3	0.0371 (15)	0.0428 (15)	0.0354 (18)	0.0078 (13)	0.0064 (13)	0.0030 (13)
N4	0.0402 (16)	0.0375 (15)	0.0351 (18)	−0.0002 (12)	0.0074 (14)	0.0041 (12)
N5	0.0322 (14)	0.0384 (14)	0.0338 (17)	0.0007 (12)	0.0023 (13)	−0.0014 (12)
N6	0.0278 (14)	0.0522 (17)	0.0384 (19)	0.0019 (12)	0.0045 (13)	0.0007 (14)
N7	0.0332 (15)	0.0420 (15)	0.0336 (17)	0.0058 (12)	0.0029 (13)	0.0011 (13)
N8	0.0302 (15)	0.0588 (18)	0.046 (2)	0.0082 (14)	0.0065 (14)	0.0031 (15)
N9	0.0390 (16)	0.0411 (15)	0.0359 (18)	−0.0031 (13)	0.0072 (14)	−0.0012 (13)
N10	0.0536 (18)	0.0399 (15)	0.0297 (18)	−0.0009 (14)	0.0050 (15)	−0.0032 (13)
C1	0.0372 (18)	0.0363 (17)	0.040 (2)	0.0013 (14)	0.0088 (16)	0.0012 (15)
C2	0.052 (2)	0.040 (2)	0.061 (3)	0.0091 (17)	0.013 (2)	0.0029 (19)
C3	0.068 (3)	0.0371 (19)	0.077 (3)	0.0017 (18)	0.025 (2)	−0.001 (2)
C4	0.064 (3)	0.040 (2)	0.074 (3)	−0.0087 (18)	0.024 (2)	−0.001 (2)
C5	0.050 (2)	0.043 (2)	0.066 (3)	−0.0102 (17)	0.009 (2)	−0.0019 (19)
C6	0.0385 (18)	0.0369 (17)	0.037 (2)	0.0002 (14)	0.0065 (16)	0.0009 (15)
C7	0.041 (2)	0.044 (2)	0.031 (2)	0.0080 (16)	0.0022 (17)	0.0026 (16)
C8	0.0329 (17)	0.0390 (17)	0.0307 (19)	0.0000 (14)	0.0029 (15)	−0.0016 (14)
C9	0.0328 (18)	0.0439 (18)	0.039 (2)	0.0017 (14)	0.0059 (16)	−0.0040 (16)
C10	0.054 (2)	0.059 (2)	0.038 (2)	0.0169 (19)	0.0064 (19)	0.0040 (18)
C11	0.053 (2)	0.072 (3)	0.047 (3)	0.023 (2)	0.009 (2)	−0.007 (2)
C12	0.044 (2)	0.076 (3)	0.042 (2)	0.004 (2)	0.0161 (19)	−0.013 (2)
C13	0.046 (2)	0.057 (2)	0.037 (2)	−0.0071 (18)	0.0110 (18)	−0.0047 (18)
C14	0.0327 (17)	0.0410 (18)	0.034 (2)	−0.0061 (14)	0.0032 (15)	−0.0052 (15)
C15	0.0314 (17)	0.0427 (18)	0.041 (2)	0.0066 (14)	0.0066 (16)	−0.0005 (15)
C16	0.0310 (17)	0.0441 (18)	0.035 (2)	−0.0021 (14)	0.0064 (16)	0.0010 (15)
C17	0.0389 (18)	0.0442 (18)	0.032 (2)	−0.0054 (15)	0.0076 (16)	−0.0009 (15)
C18	0.050 (2)	0.046 (2)	0.056 (3)	0.0009 (18)	0.004 (2)	−0.0037 (19)
C19	0.074 (3)	0.049 (2)	0.072 (3)	−0.006 (2)	0.012 (3)	−0.015 (2)
C20	0.061 (3)	0.065 (3)	0.067 (3)	−0.018 (2)	0.008 (2)	−0.023 (2)
C21	0.040 (2)	0.068 (3)	0.057 (3)	−0.0132 (19)	0.003 (2)	−0.009 (2)
C22	0.0330 (18)	0.049 (2)	0.045 (2)	−0.0049 (15)	0.0084 (17)	0.0006 (17)
C23	0.0318 (17)	0.050 (2)	0.045 (2)	−0.0024 (15)	0.0053 (16)	0.0020 (17)
C24	0.0324 (18)	0.050 (2)	0.036 (2)	0.0072 (15)	0.0068 (16)	0.0013 (16)
C25	0.0437 (19)	0.0438 (18)	0.030 (2)	0.0102 (15)	0.0083 (16)	0.0006 (15)
C26	0.052 (2)	0.051 (2)	0.050 (3)	0.0073 (18)	0.006 (2)	0.0052 (19)
C27	0.076 (3)	0.049 (2)	0.067 (3)	0.009 (2)	0.013 (3)	0.014 (2)
C28	0.072 (3)	0.061 (3)	0.080 (4)	0.031 (2)	0.017 (3)	0.023 (2)
C29	0.047 (2)	0.078 (3)	0.055 (3)	0.025 (2)	0.009 (2)	0.014 (2)
C30	0.042 (2)	0.056 (2)	0.034 (2)	0.0174 (17)	0.0107 (17)	0.0063 (17)
C31	0.0411 (19)	0.0462 (19)	0.031 (2)	−0.0019 (15)	−0.0010 (16)	−0.0008 (15)
C32	0.0377 (18)	0.0348 (17)	0.037 (2)	0.0020 (14)	0.0002 (16)	0.0012 (15)
C33	0.043 (2)	0.0390 (17)	0.038 (2)	0.0014 (15)	0.0102 (17)	0.0038 (15)
C34	0.058 (2)	0.062 (2)	0.043 (2)	−0.014 (2)	0.016 (2)	−0.003 (2)
C35	0.061 (3)	0.080 (3)	0.058 (3)	−0.020 (2)	0.020 (2)	0.002 (2)
C36	0.060 (3)	0.080 (3)	0.057 (3)	0.000 (2)	0.029 (2)	0.012 (2)
C37	0.073 (3)	0.058 (2)	0.036 (2)	0.009 (2)	0.021 (2)	0.0058 (18)
C38	0.051 (2)	0.0412 (18)	0.030 (2)	0.0043 (16)	0.0090 (17)	0.0067 (15)
Cl1	0.0785 (8)	0.0682 (7)	0.0822 (10)	0.0197 (6)	0.0213 (7)	0.0329 (6)
O1	0.202 (6)	0.101 (3)	0.129 (4)	0.045 (4)	0.054 (4)	0.023 (3)
O2	0.094 (3)	0.226 (6)	0.129 (5)	0.047 (4)	0.005 (3)	0.070 (4)
O3	0.178 (5)	0.140 (4)	0.133 (5)	−0.067 (4)	0.004 (4)	0.063 (4)
O4	0.127 (4)	0.156 (4)	0.107 (4)	0.032 (3)	0.049 (3)	0.068 (3)
Cl2	0.032 (3)	0.045 (3)	0.104 (6)	−0.0110 (19)	−0.007 (3)	−0.011 (3)
O5	0.092 (12)	0.167 (17)	0.130 (16)	−0.052 (10)	0.058 (11)	−0.013 (10)
O6	0.088 (8)	0.090 (8)	0.142 (18)	0.001 (6)	−0.012 (10)	−0.056 (10)
O7	0.157 (13)	0.176 (14)	0.145 (14)	−0.023 (11)	0.002 (11)	0.020 (11)
O8	0.077 (6)	0.082 (7)	0.130 (13)	−0.008 (5)	−0.044 (7)	−0.048 (8)
Cl2'	0.073 (4)	0.110 (5)	0.081 (3)	−0.029 (3)	0.021 (3)	−0.032 (3)
O5'	0.071 (7)	0.172 (16)	0.143 (16)	0.004 (8)	0.006 (8)	−0.025 (11)
O6'	0.083 (8)	0.127 (10)	0.128 (14)	−0.045 (7)	0.032 (8)	−0.065 (8)
O7'	0.148 (12)	0.114 (8)	0.105 (9)	−0.065 (8)	0.048 (9)	−0.040 (6)
O8'	0.141 (10)	0.160 (10)	0.084 (7)	0.031 (8)	0.005 (6)	0.006 (6)
O1S	0.074 (2)	0.099 (3)	0.098 (3)	−0.019 (2)	0.023 (2)	−0.040 (2)
C1S	0.177 (8)	0.099 (5)	0.146 (8)	−0.022 (5)	0.062 (7)	−0.028 (5)

Fe1—N7	2.095 (3)	C13—C14	1.384 (5)
Fe1—N5	2.114 (3)	C13—H13A	0.9300
Fe1—N9	2.145 (3)	C15—C16	1.500 (5)
Fe1—N3	2.156 (3)	C15—H15A	0.9700
Fe1—N1	2.324 (3)	C15—H15B	0.9700
Fe1—N2	2.326 (3)	C17—C22	1.388 (5)
N1—C15	1.479 (4)	C17—C18	1.401 (5)
N1—C7	1.488 (4)	C18—C19	1.374 (6)
N1—C1	1.489 (4)	C18—H18A	0.9300
N2—C31	1.475 (5)	C19—C20	1.376 (6)
N2—C23	1.482 (4)	C19—H19A	0.9300
N2—C6	1.499 (4)	C20—C21	1.372 (6)
N3—C8	1.305 (4)	C20—H20A	0.9300
N3—C9	1.390 (4)	C21—C22	1.379 (5)
N4—C8	1.344 (4)	C21—H21A	0.9300
N4—C14	1.382 (4)	C23—C24	1.495 (5)
N4—H4A	0.8600	C23—H23A	0.9700
N5—C16	1.312 (4)	C23—H23B	0.9700
N5—C17	1.397 (4)	C25—C30	1.389 (5)
N6—C16	1.339 (4)	C25—C26	1.394 (5)
N6—C22	1.389 (4)	C26—C27	1.369 (6)
N6—H6A	0.8600	C26—H26A	0.9300
N7—C24	1.314 (5)	C27—C28	1.389 (7)
N7—C25	1.396 (4)	C27—H27A	0.9300
N8—C24	1.350 (4)	C28—C29	1.371 (6)
N8—C30	1.385 (5)	C28—H28A	0.9300
N8—H8A	0.8600	C29—C30	1.380 (5)
N9—C32	1.305 (4)	C29—H29A	0.9300
N9—C33	1.405 (4)	C31—C32	1.493 (5)
N10—C32	1.350 (5)	C31—H31A	0.9700
N10—C38	1.375 (5)	C31—H31B	0.9700
N10—H10A	0.8600	C33—C34	1.376 (5)
C1—C2	1.532 (5)	C33—C38	1.398 (5)
C1—C6	1.537 (5)	C34—C35	1.383 (6)
C1—H1A	0.9800	C34—H34A	0.9300
C2—C3	1.510 (6)	C35—C36	1.383 (7)
C2—H2A	0.97 (5)	C35—H35A	0.9300
C2—H2B	0.90 (5)	C36—C37	1.369 (6)
C3—C4	1.503 (6)	C36—H36A	0.9300
C3—H3A	0.9700	C37—C38	1.394 (5)
C3—H3B	0.9700	C37—H37A	0.9300
C4—C5	1.521 (6)	Cl1—O2	1.346 (5)
C4—H4B	0.9700	Cl1—O1	1.364 (5)
C4—H4C	0.9700	Cl1—O3	1.413 (5)
C5—C6	1.521 (5)	Cl1—O4	1.421 (5)
C5—H5A	0.9700	Cl2—O8	1.347 (8)
C5—H5B	0.9700	Cl2—O6	1.373 (9)
C6—H6B	0.9800	Cl2—O5	1.392 (9)
C7—C8	1.483 (5)	Cl2—O7	1.441 (9)
C7—H7A	0.94 (3)	Cl2'—O5'	1.333 (15)
C7—H7B	0.94 (4)	Cl2'—O7'	1.411 (12)
C9—C10	1.390 (5)	Cl2'—O8'	1.418 (14)
C9—C14	1.409 (5)	Cl2'—O6'	1.517 (15)
C10—C11	1.375 (6)	O1S—C1S	1.414 (8)
C10—H10B	0.9300	O1S—H1S	0.9556
C11—C12	1.389 (6)	C1S—H1SA	0.9600
C11—H11A	0.9300	C1S—H1SB	0.9600
C12—C13	1.365 (6)	C1S—H1SC	0.9600
C12—H12A	0.9300
N7—Fe1—N5	132.58 (11)	C14—C13—H13A	121.8
N7—Fe1—N9	94.65 (11)	N4—C14—C13	132.6 (3)
N5—Fe1—N9	93.02 (11)	N4—C14—C9	104.9 (3)
N7—Fe1—N3	91.46 (11)	C13—C14—C9	122.4 (3)
N5—Fe1—N3	90.87 (11)	N1—C15—C16	106.5 (3)
N9—Fe1—N3	167.46 (11)	N1—C15—H15A	110.4
N7—Fe1—N1	149.54 (10)	C16—C15—H15A	110.4
N5—Fe1—N1	76.80 (10)	N1—C15—H15B	110.4
N9—Fe1—N1	90.85 (10)	C16—C15—H15B	110.4
N3—Fe1—N1	78.43 (10)	H15A—C15—H15B	108.6
N7—Fe1—N2	75.51 (10)	N5—C16—N6	112.6 (3)
N5—Fe1—N2	151.68 (10)	N5—C16—C15	121.8 (3)
N9—Fe1—N2	79.05 (11)	N6—C16—C15	125.3 (3)
N3—Fe1—N2	91.94 (11)	C22—C17—N5	109.1 (3)
N1—Fe1—N2	76.19 (10)	C22—C17—C18	120.7 (3)
C15—N1—C7	109.7 (3)	N5—C17—C18	130.2 (3)
C15—N1—C1	113.7 (3)	C19—C18—C17	116.8 (4)
C7—N1—C1	113.1 (3)	C19—C18—H18A	121.6
C15—N1—Fe1	103.09 (19)	C17—C18—H18A	121.6
C7—N1—Fe1	107.84 (19)	C18—C19—C20	121.4 (4)
C1—N1—Fe1	108.79 (19)	C18—C19—H19A	119.3
C31—N2—C23	110.2 (3)	C20—C19—H19A	119.3
C31—N2—C6	113.8 (3)	C21—C20—C19	122.6 (4)
C23—N2—C6	112.9 (3)	C21—C20—H20A	118.7
C31—N2—Fe1	106.03 (19)	C19—C20—H20A	118.7
C23—N2—Fe1	104.2 (2)	C20—C21—C22	116.4 (4)
C6—N2—Fe1	109.06 (19)	C20—C21—H21A	121.8
C8—N3—C9	106.4 (3)	C22—C21—H21A	121.8
C8—N3—Fe1	113.6 (2)	C21—C22—C17	122.0 (4)
C9—N3—Fe1	138.6 (2)	C21—C22—N6	132.9 (4)
C8—N4—C14	107.9 (3)	C17—C22—N6	105.0 (3)
C8—N4—H4A	126.1	N2—C23—C24	107.0 (3)
C14—N4—H4A	126.1	N2—C23—H23A	110.3
C16—N5—C17	105.6 (3)	C24—C23—H23A	110.3
C16—N5—Fe1	113.3 (2)	N2—C23—H23B	110.3
C17—N5—Fe1	138.4 (2)	C24—C23—H23B	110.3
C16—N6—C22	107.7 (3)	H23A—C23—H23B	108.6
C16—N6—H6A	126.1	N7—C24—N8	112.2 (3)
C22—N6—H6A	126.1	N7—C24—C23	122.0 (3)
C24—N7—C25	105.9 (3)	N8—C24—C23	125.8 (3)
C24—N7—Fe1	114.7 (2)	C30—C25—C26	120.8 (3)
C25—N7—Fe1	139.3 (2)	C30—C25—N7	108.9 (3)
C24—N8—C30	107.6 (3)	C26—C25—N7	130.1 (3)
C24—N8—H8A	126.2	C27—C26—C25	117.2 (4)
C30—N8—H8A	126.2	C27—C26—H26A	121.4
C32—N9—C33	106.2 (3)	C25—C26—H26A	121.4
C32—N9—Fe1	112.1 (2)	C26—C27—C28	121.4 (4)
C33—N9—Fe1	137.3 (3)	C26—C27—H27A	119.3
C32—N10—C38	107.7 (3)	C28—C27—H27A	119.3
C32—N10—H10A	126.2	C29—C28—C27	121.9 (4)
C38—N10—H10A	126.2	C29—C28—H28A	119.1
N1—C1—C2	114.9 (3)	C27—C28—H28A	119.1
N1—C1—C6	108.1 (3)	C28—C29—C30	117.0 (4)
C2—C1—C6	113.9 (3)	C28—C29—H29A	121.5
N1—C1—H1A	106.5	C30—C29—H29A	121.5
C2—C1—H1A	106.5	C29—C30—N8	132.9 (4)
C6—C1—H1A	106.5	C29—C30—C25	121.7 (4)
C3—C2—C1	112.9 (4)	N8—C30—C25	105.4 (3)
C3—C2—H2A	110 (3)	N2—C31—C32	110.9 (3)
C1—C2—H2A	108 (3)	N2—C31—H31A	109.5
C3—C2—H2B	110 (3)	C32—C31—H31A	109.5
C1—C2—H2B	110 (3)	N2—C31—H31B	109.5
H2A—C2—H2B	105 (4)	C32—C31—H31B	109.5
C4—C3—C2	110.6 (3)	H31A—C31—H31B	108.0
C4—C3—H3A	109.5	N9—C32—N10	112.4 (3)
C2—C3—H3A	109.5	N9—C32—C31	123.8 (3)
C4—C3—H3B	109.5	N10—C32—C31	123.9 (3)
C2—C3—H3B	109.5	C34—C33—C38	121.1 (3)
H3A—C3—H3B	108.1	C34—C33—N9	131.1 (3)
C3—C4—C5	109.9 (3)	C38—C33—N9	107.8 (3)
C3—C4—H4B	109.7	C33—C34—C35	117.1 (4)
C5—C4—H4B	109.7	C33—C34—H34A	121.4
C3—C4—H4C	109.7	C35—C34—H34A	121.4
C5—C4—H4C	109.7	C36—C35—C34	121.5 (4)
H4B—C4—H4C	108.2	C36—C35—H35A	119.2
C6—C5—C4	112.4 (3)	C34—C35—H35A	119.2
C6—C5—H5A	109.1	C37—C36—C35	122.3 (4)
C4—C5—H5A	109.1	C37—C36—H36A	118.9
C6—C5—H5B	109.1	C35—C36—H36A	118.9
C4—C5—H5B	109.1	C36—C37—C38	116.4 (4)
H5A—C5—H5B	107.8	C36—C37—H37A	121.8
N2—C6—C5	114.8 (3)	C38—C37—H37A	121.8
N2—C6—C1	108.7 (3)	N10—C38—C37	132.5 (4)
C5—C6—C1	114.2 (3)	N10—C38—C33	105.9 (3)
N2—C6—H6B	106.2	C37—C38—C33	121.5 (4)
C5—C6—H6B	106.2	O2—Cl1—O1	115.1 (4)
C1—C6—H6B	106.2	O2—Cl1—O3	107.8 (4)
C8—C7—N1	112.0 (3)	O1—Cl1—O3	106.4 (4)
C8—C7—H7A	109 (2)	O2—Cl1—O4	113.0 (3)
N1—C7—H7A	108 (2)	O1—Cl1—O4	106.9 (3)
C8—C7—H7B	110 (2)	O3—Cl1—O4	107.2 (3)
N1—C7—H7B	111 (2)	O8—Cl2—O6	101.0 (9)
H7A—C7—H7B	107 (3)	O8—Cl2—O5	126.2 (13)
N3—C8—N4	112.5 (3)	O6—Cl2—O5	102.8 (11)
N3—C8—C7	124.4 (3)	O8—Cl2—O7	108.3 (8)
N4—C8—C7	123.1 (3)	O6—Cl2—O7	115.9 (11)
C10—C9—N3	131.8 (4)	O5—Cl2—O7	103.3 (8)
C10—C9—C14	119.8 (3)	O5'—Cl2'—O7'	106.4 (14)
N3—C9—C14	108.4 (3)	O5'—Cl2'—O8'	112.4 (12)
C11—C10—C9	117.3 (4)	O7'—Cl2'—O8'	104.5 (11)
C11—C10—H10B	121.3	O5'—Cl2'—O6'	105.8 (12)
C9—C10—H10B	121.3	O7'—Cl2'—O6'	102.2 (10)
C10—C11—C12	121.7 (4)	O8'—Cl2'—O6'	123.9 (11)
C10—C11—H11A	119.1	C1S—O1S—H1S	107.9
C12—C11—H11A	119.1	O1S—C1S—H1SA	109.1
C13—C12—C11	122.3 (4)	O1S—C1S—H1SB	110.0
C13—C12—H12A	118.8	H1SA—C1S—H1SB	109.2
C11—C12—H12A	118.8	O1S—C1S—H1SC	110.7
C12—C13—C14	116.3 (4)	H1SA—C1S—H1SC	109.2
C12—C13—H13A	121.8	H1SB—C1S—H1SC	108.5

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1i	0.86	2.10	2.952 (6)	171
N6—H6A···O6'ii	0.86	2.02	2.852 (15)	162
N6—H6A···O6ii	0.86	2.13	2.955 (16)	162
N8—H8A···O1S	0.86	1.94	2.790 (5)	170
N10—H10A···O7'iii	0.86	2.04	2.896 (10)	176
N10—H10A···O8iii	0.86	2.01	2.787 (12)	150
O1S—H1S···O3iv	0.96	1.88	2.813 (6)	166
C7—H7B···O4i	0.94 (4)	2.34 (4)	3.202 (6)	152 (3)
C23—H23A···O2iv	0.97	2.40	3.318 (6)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1i	0.86	2.10	2.952 (6)	171
N6—H6A⋯O6′ii	0.86	2.02	2.852 (15)	162
N6—H6A⋯O6ii	0.86	2.13	2.955 (16)	162
N8—H8A⋯O1S	0.86	1.94	2.790 (5)	170
N10—H10A⋯O7′iii	0.86	2.04	2.896 (10)	176
N10—H10A⋯O8iii	0.86	2.01	2.787 (12)	150
O1S—H1S⋯O3iv	0.96	1.88	2.813 (6)	166
C7—H7B⋯O4i	0.94 (4)	2.34 (4)	3.202 (6)	152 (3)
C23—H23A⋯O2iv	0.97	2.40	3.318 (6)	158

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