Dichlorido[tris­(1H-benzimidazol-2-ylmeth­yl)amine-κ4N,N3,N3′,N3′′]iron(III) chloride tetra­hydro­furan monosolvate monohydrate

Wang, D.

doi:10.1107/S1600536809023423

metal-organic compounds

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Volume 65| Part 7| July 2009| Page m828

doi:10.1107/S1600536809023423

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Dichlorido[tris(1H-benzimidazol-2-ylmethyl)amine-κ⁴N,N³,N^3′,N^3′′]iron(III) chloride tetrahydrofuran monosolvate monohydrate

Dong'e Wang ^a ^*

^aDepartment of Chemistry, Kashgar Teachers College, Kashgar 844000, People's Republic of China
^*Correspondence e-mail: wdexjks@yahoo.com.cn

(Received 12 June 2009; accepted 18 June 2009; online 27 June 2009)

In the title compound, [FeCl₂(C₂₄H₂₁N₇)]Cl·C₄H₈O·H₂O, the Fe^III atom is coordinated by four N atoms of the polybenzimidazole ligand and two Cl atoms in a distorted octahedral environment. The cation, anion, the uncoordinated water molecule and the THF solvent molecule are linked by hydrogen bonds into a three-dimensional network structure. The THF molecule is disordered with two sets of sites in a 0.58 (1):0.42 (2) ratio..

Related literature

For the synthesis of the ligand, see: Hendriks et al. (1982 ). For benzimidazole-like ligands, see: Moon & Soo Lah (2002 ).

Experimental

Crystal data

[FeCl₂(C₂₄H₂₁N₇)]Cl·C₄H₈O·H₂O
M_r = 659.80
Monoclinic, P 2₁ /c
a = 10.2898 (4) Å
b = 13.7475 (5) Å
c = 21.5271 (7) Å
β = 101.614 (1)°
V = 2982.85 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 292 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.844, T_max = 0.923
17337 measured reflections
5527 independent reflections
3999 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.116
S = 1.00
5527 reflections
404 parameters
21 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯Cl3	0.828 (18)	2.34 (2)	3.136 (3)	160 (4)
O1W—H1B⋯Cl1	0.831 (19)	2.51 (3)	3.267 (3)	152 (4)
N2—H2⋯Cl3ⁱ	0.859 (18)	2.25 (2)	3.070 (3)	159 (3)
N4—H4⋯O1Wⁱⁱ	0.862 (18)	1.96 (2)	2.795 (4)	162 (3)
N6—H6⋯O1ⁱⁱⁱ	0.852 (18)	1.91 (2)	2.741 (4)	163 (3)
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023423/ng2597sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023423/ng2597Isup2.hkl

checkCIF report

Comment top

Tris(1-H-benzimidazol-2-ylmethl)amine-N, H₃ntb, is a typical heterocyclic ligand with nitrogen as the donor atom. Over the past decades, there has been an interest in the Fe^III ions coordinated to benzimidazole-rich ligands in particular with respect to relationships between the activity and structural properties of metalloenzymes such as superoxide dismutases (SOD) (Moon & Soo Lah, 2002). Here, we report our findings in the title compound (I).

In compound (I) (Fig.1), the asymmetric unit consists of one [Fe(H₃ntb).Cl₂]⁺ cation, one Cl^- anion and each one water and tetrahydrofuran molecules. The Fe^III is coordinated by four nitrogen atoms of a tetradentate liangd ntb, and two chloride anions, forming a distorted octahedron. The Fe—N_amine bond length (2.355 (2) Å) is more longer than the mean bond length of Fe—N_{benzimidazole} (2.101 (2) Å), which is owing to the steric requirement. No other abnormal bond lengths and bond angles are observed in (I).

In the crystal, the ions are joined together by extensive hydrogen bondings and and π-π interactions, which lead to the formation of a three dimensional network (Fig.2).

Related literature top

For the synthesis of the ligand, see: Hendriks et al. (1982). For benzimidazole-like ligands, see: Moon & Soo Lah (2002); Sheldrick (2001).

Experimental top

All reagants and solvents were used as obtained without further purification. H₃ntb was synthesized according to the literature (Hendriks et al.,1982). A mixture of FeCl₃ (0.0324 g, 0.2 mmol), H₃ntb(0.0814 g, 0.2 mmol), tetrahydrofuran (5 ml)was transferred to and sealed in a Parr Teflon-lined stainless steel vessel (15 ml), which was heated at 393 K for 3 days. After cooling to room temperature, the red block crystals of I were filtered off, washed with distilled water, and dried at ambient temperature (39 mg, yield 28.7% based on FeCl₃).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Spek, 2009).

Figures top

	Fig. 1. A view of the structure of (I), with displacement ellipsoids drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Plot of the crystal packing showing the linkage of the molecules by H-bonding shown as dashed lines.

Dichlorido[tris(1H-benzimidazol-2-ylmethyl)amine- κ⁴N,N³,N^3',N^3'']iron(III) chloride tetrahydrofuran monosolvate monohydrate top

Crystal data top

[FeCl₂(C₂₄H₂₁N₇)]Cl·C₄H₈O·H₂O	F(000) = 1364
M_r = 659.80	D_x = 1.469 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3638 reflections
a = 10.2898 (4) Å	θ = 2.4–22.2°
b = 13.7475 (5) Å	µ = 0.81 mm⁻¹
c = 21.5271 (7) Å	T = 292 K
β = 101.614 (1)°	Block, red
V = 2982.85 (19) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5527 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	3999 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
0.3° wide ω exposures scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→12
T_min = 0.844, T_max = 0.923	k = −16→15
17337 measured reflections	l = −26→24

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0587P)²] where P = (F_o² + 2F_c²)/3
5527 reflections	(Δ/σ)_max < 0.001
404 parameters	Δρ_max = 0.33 e Å⁻³
21 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[FeCl₂(C₂₄H₂₁N₇)]Cl·C₄H₈O·H₂O	V = 2982.85 (19) Å³
M_r = 659.80	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2898 (4) Å	µ = 0.81 mm⁻¹
b = 13.7475 (5) Å	T = 292 K
c = 21.5271 (7) Å	0.20 × 0.15 × 0.10 mm
β = 101.614 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5527 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3999 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.923	R_int = 0.046
17337 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	21 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.33 e Å⁻³
5527 reflections	Δρ_min = −0.25 e Å⁻³
404 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe1	0.94620 (4)	0.27332 (3)	0.810133 (19)	0.03211 (14)
Cl1	1.00873 (8)	0.17478 (6)	0.73359 (4)	0.0445 (2)
Cl2	0.86507 (8)	0.39490 (6)	0.74462 (4)	0.0476 (2)
N1	0.7813 (2)	0.18448 (19)	0.81255 (12)	0.0369 (6)
N2	0.6965 (3)	0.0441 (2)	0.83683 (14)	0.0482 (7)
H2	0.694 (3)	−0.0126 (16)	0.8535 (15)	0.058*
N3	0.9114 (2)	0.33689 (18)	0.89433 (11)	0.0367 (6)
N4	0.9099 (3)	0.3256 (2)	0.99701 (12)	0.0439 (7)
H4	0.924 (3)	0.296 (2)	1.0330 (11)	0.053*
N5	1.1468 (2)	0.30502 (18)	0.84551 (11)	0.0342 (6)
N6	1.3466 (2)	0.2668 (2)	0.89915 (13)	0.0446 (7)
H6	1.413 (2)	0.237 (2)	0.9213 (14)	0.054*
N7	1.0223 (2)	0.15132 (18)	0.88547 (11)	0.0361 (6)
C1	0.5896 (3)	0.0998 (3)	0.80784 (15)	0.0452 (8)
C2	0.4545 (3)	0.0799 (3)	0.79198 (18)	0.0604 (10)
H2A	0.4191	0.0210	0.8019	0.072*
C3	0.3760 (4)	0.1536 (3)	0.76056 (18)	0.0635 (11)
H3	0.2851	0.1433	0.7487	0.076*
C4	0.4273 (3)	0.2419 (3)	0.74607 (18)	0.0596 (10)
H4A	0.3703	0.2893	0.7251	0.071*
C5	0.5621 (3)	0.2610 (3)	0.76226 (16)	0.0508 (9)
H5	0.5968	0.3203	0.7526	0.061*
C6	0.6426 (3)	0.1889 (2)	0.79315 (14)	0.0392 (8)
C7	0.8062 (3)	0.0962 (2)	0.83803 (15)	0.0407 (8)
C8	0.9449 (3)	0.0627 (2)	0.86263 (16)	0.0428 (8)
H8A	0.9477	0.0167	0.8970	0.051*
H8B	0.9806	0.0315	0.8292	0.051*
C9	0.9971 (3)	0.1834 (3)	0.94789 (15)	0.0483 (9)
H9A	0.9372	0.1376	0.9619	0.058*
H9B	1.0800	0.1825	0.9787	0.058*
C10	0.9390 (3)	0.2821 (2)	0.94594 (14)	0.0368 (7)
C11	0.8612 (3)	0.4177 (3)	0.97900 (15)	0.0424 (8)
C12	0.8176 (3)	0.4915 (3)	1.01283 (17)	0.0539 (9)
H12	0.8151	0.4852	1.0556	0.065*
C13	0.7781 (3)	0.5753 (3)	0.9795 (2)	0.0586 (10)
H13	0.7479	0.6271	1.0005	0.070*
C14	0.7816 (3)	0.5853 (3)	0.91592 (18)	0.0516 (9)
H14	0.7555	0.6438	0.8955	0.062*
C15	0.8229 (3)	0.5102 (2)	0.88240 (16)	0.0451 (8)
H15	0.8239	0.5166	0.8395	0.054*
C16	0.8624 (3)	0.4259 (2)	0.91432 (15)	0.0378 (7)
C17	1.1664 (3)	0.1394 (2)	0.88752 (16)	0.0412 (8)
H17A	1.2099	0.1126	0.9281	0.049*
H17B	1.1807	0.0956	0.8542	0.049*
C18	1.2211 (3)	0.2369 (2)	0.87831 (14)	0.0349 (7)
C19	1.3560 (3)	0.3620 (2)	0.87884 (14)	0.0402 (8)
C20	1.4596 (3)	0.4284 (3)	0.88702 (17)	0.0552 (10)
H20	1.5444	0.4124	0.9089	0.066*
C21	1.4307 (3)	0.5183 (3)	0.86141 (17)	0.0568 (10)
H21	1.4979	0.5645	0.8657	0.068*
C22	1.3051 (3)	0.5433 (3)	0.82922 (16)	0.0514 (9)
H22	1.2898	0.6062	0.8136	0.062*
C23	1.2022 (3)	0.4777 (2)	0.81965 (15)	0.0421 (8)
H23	1.1181	0.4944	0.7973	0.051*
C24	1.2294 (3)	0.3859 (2)	0.84485 (14)	0.0361 (7)
O1W	0.9939 (3)	0.2955 (2)	0.60165 (12)	0.0715 (8)
H1A	1.073 (2)	0.302 (4)	0.599 (2)	0.107*
H1B	0.984 (4)	0.283 (4)	0.6383 (12)	0.107*
Cl3	1.26515 (10)	0.36822 (8)	0.57345 (5)	0.0690 (3)
O1	0.5693 (3)	0.2940 (2)	0.48243 (13)	0.0781 (9)
C25	0.5735 (5)	0.2366 (3)	0.5376 (2)	0.0854 (14)
H25A	0.6237	0.1776	0.5349	0.102*
H25B	0.4842	0.2184	0.5413	0.102*
C26	0.6369 (5)	0.2936 (4)	0.5937 (2)	0.0999 (17)
H26A	0.7268	0.2714	0.6098	0.120*	0.58
H26B	0.5867	0.2888	0.6272	0.120*	0.58
H26C	0.7138	0.2598	0.6174	0.120*	0.42
H26D	0.5754	0.3058	0.6215	0.120*	0.42
C27	0.6360 (17)	0.3975 (6)	0.5690 (5)	0.088 (6)	0.58
H27A	0.7114	0.4345	0.5913	0.106*	0.58
H27B	0.5545	0.4312	0.5717	0.106*	0.58
C28	0.6462 (10)	0.3772 (7)	0.4990 (5)	0.084 (4)	0.58
H28A	0.6115	0.4314	0.4719	0.101*	0.58
H28B	0.7376	0.3657	0.4956	0.101*	0.58
C28'	0.5865 (15)	0.3944 (7)	0.4996 (6)	0.085 (5)	0.42
H28C	0.5024	0.4247	0.5018	0.102*	0.42
H28D	0.6277	0.4299	0.4698	0.102*	0.42
C27'	0.679 (2)	0.3894 (9)	0.5661 (6)	0.084 (7)	0.42
H27C	0.7717	0.3873	0.5626	0.101*	0.42
H27D	0.6653	0.4447	0.5920	0.101*	0.42

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0333 (2)	0.0318 (3)	0.0293 (2)	0.00082 (18)	0.00167 (17)	0.00084 (19)
Cl1	0.0463 (4)	0.0451 (5)	0.0424 (5)	0.0001 (4)	0.0096 (3)	−0.0090 (4)
Cl2	0.0550 (5)	0.0437 (5)	0.0397 (5)	0.0064 (4)	−0.0010 (4)	0.0092 (4)
N1	0.0365 (14)	0.0339 (16)	0.0391 (15)	−0.0016 (11)	0.0046 (11)	0.0021 (12)
N2	0.0503 (17)	0.0416 (18)	0.0534 (19)	−0.0107 (15)	0.0116 (14)	0.0037 (15)
N3	0.0415 (14)	0.0363 (16)	0.0308 (14)	0.0033 (11)	0.0037 (11)	−0.0003 (12)
N4	0.0504 (16)	0.052 (2)	0.0296 (15)	0.0020 (14)	0.0084 (13)	0.0017 (14)
N5	0.0340 (13)	0.0291 (14)	0.0363 (15)	−0.0007 (11)	−0.0006 (11)	−0.0004 (12)
N6	0.0359 (15)	0.0472 (19)	0.0453 (17)	0.0058 (13)	−0.0050 (12)	0.0021 (14)
N7	0.0405 (14)	0.0316 (15)	0.0348 (14)	0.0048 (11)	0.0041 (11)	0.0013 (12)
C1	0.0414 (18)	0.055 (2)	0.0401 (19)	−0.0032 (16)	0.0109 (15)	−0.0033 (17)
C2	0.049 (2)	0.078 (3)	0.058 (2)	−0.020 (2)	0.0176 (18)	−0.010 (2)
C3	0.0372 (19)	0.098 (3)	0.056 (2)	−0.004 (2)	0.0101 (17)	−0.018 (2)
C4	0.042 (2)	0.077 (3)	0.057 (2)	0.0144 (19)	0.0026 (17)	0.000 (2)
C5	0.049 (2)	0.054 (2)	0.050 (2)	0.0040 (17)	0.0093 (17)	−0.0025 (18)
C6	0.0365 (17)	0.047 (2)	0.0348 (18)	0.0014 (15)	0.0079 (14)	−0.0036 (15)
C7	0.0407 (17)	0.040 (2)	0.0416 (19)	−0.0035 (15)	0.0084 (14)	−0.0015 (16)
C8	0.0458 (18)	0.0325 (19)	0.048 (2)	0.0013 (14)	0.0037 (15)	0.0033 (16)
C9	0.061 (2)	0.047 (2)	0.0361 (19)	0.0098 (17)	0.0095 (16)	0.0042 (16)
C10	0.0384 (16)	0.040 (2)	0.0309 (17)	−0.0004 (14)	0.0047 (13)	0.0000 (15)
C11	0.0401 (17)	0.044 (2)	0.043 (2)	−0.0008 (15)	0.0082 (15)	−0.0065 (16)
C12	0.057 (2)	0.058 (3)	0.050 (2)	−0.0008 (18)	0.0179 (17)	−0.016 (2)
C13	0.056 (2)	0.049 (2)	0.074 (3)	0.0028 (18)	0.0196 (19)	−0.023 (2)
C14	0.0475 (19)	0.043 (2)	0.062 (2)	0.0049 (16)	0.0045 (17)	−0.0037 (19)
C15	0.0487 (19)	0.037 (2)	0.048 (2)	0.0072 (15)	0.0054 (15)	−0.0022 (17)
C16	0.0340 (16)	0.040 (2)	0.0391 (19)	0.0007 (14)	0.0059 (13)	−0.0056 (15)
C17	0.0386 (17)	0.0341 (19)	0.048 (2)	0.0068 (14)	0.0005 (14)	0.0033 (16)
C18	0.0360 (16)	0.0300 (18)	0.0352 (17)	0.0039 (13)	−0.0010 (13)	−0.0027 (14)
C19	0.0375 (17)	0.041 (2)	0.0401 (19)	−0.0015 (14)	0.0025 (14)	−0.0003 (16)
C20	0.0357 (18)	0.070 (3)	0.054 (2)	−0.0071 (17)	−0.0051 (16)	0.000 (2)
C21	0.051 (2)	0.056 (3)	0.061 (2)	−0.0186 (18)	0.0048 (18)	0.004 (2)
C22	0.058 (2)	0.047 (2)	0.048 (2)	−0.0103 (17)	0.0088 (17)	0.0069 (18)
C23	0.0450 (18)	0.042 (2)	0.0383 (18)	−0.0008 (15)	0.0056 (14)	0.0053 (16)
C24	0.0380 (16)	0.039 (2)	0.0295 (16)	−0.0019 (14)	0.0038 (13)	−0.0051 (14)
O1W	0.082 (2)	0.088 (2)	0.0449 (16)	−0.0061 (18)	0.0147 (14)	−0.0079 (16)
Cl3	0.0691 (6)	0.0644 (7)	0.0706 (7)	−0.0083 (5)	0.0075 (5)	−0.0187 (5)
O1	0.081 (2)	0.082 (2)	0.0597 (19)	−0.0229 (17)	−0.0139 (14)	−0.0003 (17)
C25	0.083 (3)	0.075 (3)	0.093 (4)	−0.005 (2)	0.006 (3)	0.013 (3)
C26	0.102 (4)	0.119 (5)	0.072 (3)	−0.026 (3)	0.002 (3)	−0.006 (3)
C27	0.083 (9)	0.089 (10)	0.086 (10)	−0.010 (7)	0.001 (6)	−0.027 (7)
C28	0.072 (7)	0.078 (7)	0.105 (9)	−0.002 (5)	0.024 (6)	0.026 (6)
C28'	0.088 (12)	0.079 (11)	0.091 (11)	−0.024 (8)	0.023 (9)	0.000 (8)
C27'	0.087 (14)	0.069 (11)	0.080 (13)	0.020 (7)	−0.021 (8)	−0.021 (8)

Geometric parameters (Å, º) top

Fe1—N5	2.097 (2)	C13—C14	1.384 (5)
Fe1—N1	2.100 (2)	C13—H13	0.9300
Fe1—N3	2.107 (2)	C14—C15	1.375 (4)
Fe1—Cl2	2.2373 (9)	C14—H14	0.9300
Fe1—Cl1	2.3219 (9)	C15—C16	1.367 (4)
Fe1—N7	2.355 (2)	C15—H15	0.9300
Cl1—H1B	2.51 (3)	C17—C18	1.482 (4)
N1—C7	1.335 (4)	C17—H17A	0.9700
N1—C6	1.405 (4)	C17—H17B	0.9700
N2—C7	1.333 (4)	C19—C20	1.387 (4)
N2—C1	1.382 (4)	C19—C24	1.399 (4)
N2—H2	0.859 (18)	C20—C21	1.361 (5)
N3—C10	1.325 (4)	C20—H20	0.9300
N3—C16	1.422 (4)	C21—C22	1.381 (5)
N4—C10	1.338 (4)	C21—H21	0.9300
N4—C11	1.388 (4)	C22—C23	1.375 (4)
N4—H4	0.862 (18)	C22—H22	0.9300
N5—C18	1.320 (4)	C23—C24	1.379 (4)
N5—C24	1.402 (4)	C23—H23	0.9300
N6—C18	1.343 (4)	O1W—H1A	0.828 (18)
N6—C19	1.389 (4)	O1W—H1B	0.831 (19)
N6—H6	0.852 (18)	Cl3—H1A	2.34 (2)
N7—C8	1.484 (4)	O1—C28	1.395 (8)
N7—C17	1.484 (4)	O1—C25	1.420 (5)
N7—C9	1.486 (4)	O1—C28'	1.430 (9)
C1—C2	1.391 (4)	C25—C26	1.476 (5)
C1—C6	1.403 (4)	C25—H25A	0.9700
C2—C3	1.384 (5)	C25—H25B	0.9700
C2—H2A	0.9300	C26—C27	1.523 (8)
C3—C4	1.385 (6)	C26—C27'	1.544 (9)
C3—H3	0.9300	C26—H26A	0.9700
C4—C5	1.386 (5)	C26—H26B	0.9700
C4—H4A	0.9300	C26—H26C	0.9700
C5—C6	1.374 (5)	C26—H26D	0.9700
C5—H5	0.9300	C27—C28	1.556 (9)
C7—C8	1.492 (4)	C27—H27A	0.9700
C8—H8A	0.9700	C27—H27B	0.9700
C8—H8B	0.9700	C28—H28A	0.9700
C9—C10	1.479 (4)	C28—H28B	0.9700
C9—H9A	0.9700	C28'—C27'	1.553 (10)
C9—H9B	0.9700	C28'—H28C	0.9700
C11—C12	1.376 (5)	C28'—H28D	0.9700
C11—C16	1.400 (4)	C27'—H27C	0.9700
C12—C13	1.374 (5)	C27'—H27D	0.9700
C12—H12	0.9300

N5—Fe1—N1	148.56 (10)	C15—C14—H14	119.4
N5—Fe1—N3	85.80 (9)	C13—C14—H14	119.4
N1—Fe1—N3	86.65 (10)	C16—C15—C14	117.7 (3)
N5—Fe1—Cl2	106.78 (7)	C16—C15—H15	121.1
N1—Fe1—Cl2	104.43 (7)	C14—C15—H15	121.1
N3—Fe1—Cl2	97.23 (7)	C15—C16—C11	120.4 (3)
N5—Fe1—Cl1	89.19 (7)	C15—C16—N3	131.7 (3)
N1—Fe1—Cl1	91.09 (7)	C11—C16—N3	107.9 (3)
N3—Fe1—Cl1	166.40 (7)	C18—C17—N7	107.5 (2)
Cl2—Fe1—Cl1	96.32 (3)	C18—C17—H17A	110.2
N5—Fe1—N7	74.41 (9)	N7—C17—H17A	110.2
N1—Fe1—N7	74.16 (9)	C18—C17—H17B	110.2
N3—Fe1—N7	78.09 (9)	N7—C17—H17B	110.2
Cl2—Fe1—N7	175.13 (7)	H17A—C17—H17B	108.5
Cl1—Fe1—N7	88.40 (6)	N5—C18—N6	112.1 (3)
Fe1—Cl1—H1B	103.7 (10)	N5—C18—C17	121.2 (3)
C7—N1—C6	105.1 (2)	N6—C18—C17	126.7 (3)
C7—N1—Fe1	116.72 (19)	C20—C19—N6	132.9 (3)
C6—N1—Fe1	138.1 (2)	C20—C19—C24	121.5 (3)
C7—N2—C1	107.7 (3)	N6—C19—C24	105.6 (3)
C7—N2—H2	125 (2)	C21—C20—C19	116.5 (3)
C1—N2—H2	127 (2)	C21—C20—H20	121.8
C10—N3—C16	105.4 (2)	C19—C20—H20	121.8
C10—N3—Fe1	116.1 (2)	C20—C21—C22	122.4 (3)
C16—N3—Fe1	138.5 (2)	C20—C21—H21	118.8
C10—N4—C11	107.9 (3)	C22—C21—H21	118.8
C10—N4—H4	120 (2)	C23—C22—C21	121.8 (3)
C11—N4—H4	132 (2)	C23—C22—H22	119.1
C18—N5—C24	106.3 (2)	C21—C22—H22	119.1
C18—N5—Fe1	118.0 (2)	C22—C23—C24	116.8 (3)
C24—N5—Fe1	135.7 (2)	C22—C23—H23	121.6
C18—N6—C19	107.9 (2)	C24—C23—H23	121.6
C18—N6—H6	130 (2)	C23—C24—C19	121.0 (3)
C19—N6—H6	122 (2)	C23—C24—N5	130.9 (3)
C8—N7—C17	112.7 (2)	C19—C24—N5	108.1 (3)
C8—N7—C9	111.3 (2)	H1A—O1W—H1B	113 (3)
C17—N7—C9	111.2 (2)	C28—O1—C25	108.8 (5)
C8—N7—Fe1	105.93 (17)	C25—O1—C28'	109.8 (6)
C17—N7—Fe1	106.90 (17)	C28—O1—H4A	93.5
C9—N7—Fe1	108.49 (18)	O1—C25—C26	108.8 (3)
N2—C1—C2	131.9 (3)	O1—C25—H25A	109.9
N2—C1—C6	106.0 (3)	C26—C25—H25A	109.9
C2—C1—C6	122.0 (3)	O1—C25—H25B	109.9
C3—C2—C1	115.6 (4)	C26—C25—H25B	109.9
C3—C2—H2A	122.2	H25A—C25—H25B	108.3
C1—C2—H2A	122.2	C25—C26—C27	104.0 (5)
C2—C3—C4	122.7 (3)	C25—C26—C27'	104.5 (6)
C2—C3—H3	118.6	C25—C26—H26A	111.0
C4—C3—H3	118.6	C27—C26—H26A	111.0
C3—C4—C5	121.1 (4)	C27'—C26—H26A	94.8
C3—C4—H4A	119.4	C25—C26—H26B	111.0
C5—C4—H4A	119.4	C27—C26—H26B	111.0
C6—C5—C4	117.4 (4)	C27'—C26—H26B	125.4
C6—C5—H5	121.3	H26A—C26—H26B	109.0
C4—C5—H5	121.3	C25—C26—H26C	110.8
C5—C6—C1	121.1 (3)	C27—C26—H26C	125.4
C5—C6—N1	130.7 (3)	C27'—C26—H26C	110.4
C1—C6—N1	108.2 (3)	H26B—C26—H26C	94.3
N2—C7—N1	112.9 (3)	C25—C26—H26D	111.2
N2—C7—C8	126.0 (3)	C27'—C26—H26D	111.1
N1—C7—C8	121.1 (3)	H26A—C26—H26D	121.8
N7—C8—C7	106.0 (2)	H26C—C26—H26D	108.7
N7—C8—H8A	110.5	C26—C27—C28	100.0 (7)
C7—C8—H8A	110.5	C26—C27—H27A	111.8
N7—C8—H8B	110.5	C28—C27—H27A	111.8
C7—C8—H8B	110.5	C26—C27—H27B	111.8
H8A—C8—H8B	108.7	C28—C27—H27B	111.8
C10—C9—N7	112.9 (3)	H27A—C27—H27B	109.5
C10—C9—H9A	109.0	O1—C28—C27	104.4 (7)
N7—C9—H9A	109.0	O1—C28—H28A	110.9
C10—C9—H9B	109.0	C27—C28—H28A	110.9
N7—C9—H9B	109.0	O1—C28—H28B	110.9
H9A—C9—H9B	107.8	C27—C28—H28B	110.9
N3—C10—N4	112.9 (3)	H28A—C28—H28B	108.9
N3—C10—C9	124.3 (3)	O1—C28'—C27'	102.5 (8)
N4—C10—C9	122.9 (3)	O1—C28'—H28C	111.3
C12—C11—N4	131.5 (3)	C27'—C28'—H28C	111.3
C12—C11—C16	122.5 (3)	O1—C28'—H28D	111.3
N4—C11—C16	106.0 (3)	C27'—C28'—H28D	111.3
C13—C12—C11	115.9 (3)	H28C—C28'—H28D	109.2
C13—C12—H12	122.1	C26—C27'—C28'	102.9 (8)
C11—C12—H12	122.1	C26—C27'—H27C	111.2
C12—C13—C14	122.4 (3)	C28'—C27'—H27C	111.2
C12—C13—H13	118.8	C26—C27'—H27D	111.2
C14—C13—H13	118.8	C28'—C27'—H27D	111.2
C15—C14—C13	121.1 (4)	H27C—C27'—H27D	109.1

N5—Fe1—Cl1—H1B	−96.2 (10)	N1—C7—C8—N7	30.8 (4)
N1—Fe1—Cl1—H1B	115.2 (10)	C8—N7—C9—C10	−118.9 (3)
N3—Fe1—Cl1—H1B	−164.5 (10)	C17—N7—C9—C10	114.5 (3)
Cl2—Fe1—Cl1—H1B	10.6 (10)	Fe1—N7—C9—C10	−2.7 (3)
N7—Fe1—Cl1—H1B	−170.7 (10)	C16—N3—C10—N4	1.5 (3)
N5—Fe1—N1—C7	−20.2 (3)	Fe1—N3—C10—N4	−177.65 (19)
N3—Fe1—N1—C7	−96.6 (2)	C16—N3—C10—C9	−177.9 (3)
Cl2—Fe1—N1—C7	166.8 (2)	Fe1—N3—C10—C9	2.9 (4)
Cl1—Fe1—N1—C7	70.0 (2)	C11—N4—C10—N3	−1.2 (3)
N7—Fe1—N1—C7	−18.0 (2)	C11—N4—C10—C9	178.3 (3)
N5—Fe1—N1—C6	161.4 (3)	N7—C9—C10—N3	0.2 (5)
N3—Fe1—N1—C6	85.1 (3)	N7—C9—C10—N4	−179.2 (3)
Cl2—Fe1—N1—C6	−11.6 (3)	C10—N4—C11—C12	−179.8 (3)
Cl1—Fe1—N1—C6	−108.4 (3)	C10—N4—C11—C16	0.4 (3)
N7—Fe1—N1—C6	163.6 (3)	N4—C11—C12—C13	178.6 (3)
N5—Fe1—N3—C10	−78.2 (2)	C16—C11—C12—C13	−1.5 (5)
N1—Fe1—N3—C10	71.3 (2)	C11—C12—C13—C14	0.0 (5)
Cl2—Fe1—N3—C10	175.4 (2)	C12—C13—C14—C15	1.3 (5)
Cl1—Fe1—N3—C10	−9.5 (4)	C13—C14—C15—C16	−1.0 (5)
N7—Fe1—N3—C10	−3.2 (2)	C14—C15—C16—C11	−0.5 (5)
N5—Fe1—N3—C16	103.0 (3)	C14—C15—C16—N3	−179.0 (3)
N1—Fe1—N3—C16	−107.5 (3)	C12—C11—C16—C15	1.8 (5)
Cl2—Fe1—N3—C16	−3.4 (3)	N4—C11—C16—C15	−178.3 (3)
Cl1—Fe1—N3—C16	171.7 (2)	C12—C11—C16—N3	−179.3 (3)
N7—Fe1—N3—C16	178.0 (3)	N4—C11—C16—N3	0.5 (3)
N1—Fe1—N5—C18	16.6 (3)	C10—N3—C16—C15	177.4 (3)
N3—Fe1—N5—C18	93.2 (2)	Fe1—N3—C16—C15	−3.7 (5)
Cl2—Fe1—N5—C18	−170.5 (2)	C10—N3—C16—C11	−1.2 (3)
Cl1—Fe1—N5—C18	−74.2 (2)	Fe1—N3—C16—C11	177.6 (2)
N7—Fe1—N5—C18	14.4 (2)	C8—N7—C17—C18	151.7 (3)
N1—Fe1—N5—C24	−161.7 (2)	C9—N7—C17—C18	−82.5 (3)
N3—Fe1—N5—C24	−85.1 (3)	Fe1—N7—C17—C18	35.7 (3)
Cl2—Fe1—N5—C24	11.2 (3)	C24—N5—C18—N6	−0.2 (3)
Cl1—Fe1—N5—C24	107.6 (3)	Fe1—N5—C18—N6	−178.9 (2)
N7—Fe1—N5—C24	−163.9 (3)	C24—N5—C18—C17	−178.6 (3)
N5—Fe1—N7—C8	−148.3 (2)	Fe1—N5—C18—C17	2.7 (4)
N1—Fe1—N7—C8	32.90 (18)	C19—N6—C18—N5	0.2 (4)
N3—Fe1—N7—C8	122.78 (19)	C19—N6—C18—C17	178.5 (3)
Cl1—Fe1—N7—C8	−58.69 (18)	N7—C17—C18—N5	−28.4 (4)
N5—Fe1—N7—C17	−27.88 (18)	N7—C17—C18—N6	153.5 (3)
N1—Fe1—N7—C17	153.3 (2)	C18—N6—C19—C20	179.1 (4)
N3—Fe1—N7—C17	−116.80 (19)	C18—N6—C19—C24	−0.2 (3)
Cl1—Fe1—N7—C17	61.73 (17)	N6—C19—C20—C21	−177.9 (4)
N5—Fe1—N7—C9	92.1 (2)	C24—C19—C20—C21	1.3 (5)
N1—Fe1—N7—C9	−86.7 (2)	C19—C20—C21—C22	0.4 (6)
N3—Fe1—N7—C9	3.18 (19)	C20—C21—C22—C23	−1.7 (6)
Cl1—Fe1—N7—C9	−178.29 (19)	C21—C22—C23—C24	1.2 (5)
C7—N2—C1—C2	176.9 (3)	C22—C23—C24—C19	0.5 (5)
C7—N2—C1—C6	−1.2 (4)	C22—C23—C24—N5	177.4 (3)
N2—C1—C2—C3	−177.6 (3)	C20—C19—C24—C23	−1.8 (5)
C6—C1—C2—C3	0.3 (5)	N6—C19—C24—C23	177.6 (3)
C1—C2—C3—C4	−0.6 (5)	C20—C19—C24—N5	−179.3 (3)
C2—C3—C4—C5	0.4 (6)	N6—C19—C24—N5	0.1 (3)
C3—C4—C5—C6	0.0 (5)	C18—N5—C24—C23	−177.2 (3)
C4—C5—C6—C1	−0.3 (5)	Fe1—N5—C24—C23	1.3 (5)
C4—C5—C6—N1	176.4 (3)	C18—N5—C24—C19	0.0 (3)
N2—C1—C6—C5	178.5 (3)	Fe1—N5—C24—C19	178.5 (2)
C2—C1—C6—C5	0.1 (5)	C28—O1—C25—C26	10.0 (7)
N2—C1—C6—N1	1.2 (3)	C28'—O1—C25—C26	−18.6 (8)
C2—C1—C6—N1	−177.2 (3)	H4A—O1—C25—C26	−61.4
C7—N1—C6—C5	−177.6 (3)	O1—C25—C26—C27	14.7 (8)
Fe1—N1—C6—C5	0.9 (5)	O1—C25—C26—C27'	−3.7 (11)
C7—N1—C6—C1	−0.6 (3)	C25—C26—C27—C28	−30.5 (10)
Fe1—N1—C6—C1	177.9 (2)	C27'—C26—C27—C28	64 (2)
C1—N2—C7—N1	0.9 (4)	C25—O1—C28—C27	−30.0 (10)
C1—N2—C7—C8	−177.3 (3)	C28'—O1—C28—C27	67.0 (18)
C6—N1—C7—N2	−0.1 (4)	H4A—O1—C28—C27	6.6
Fe1—N1—C7—N2	−179.0 (2)	C26—C27—C28—O1	37.2 (11)
C6—N1—C7—C8	178.1 (3)	C28—O1—C28'—C27'	−60.6 (18)
Fe1—N1—C7—C8	−0.8 (4)	C25—O1—C28'—C27'	32.1 (13)
C17—N7—C8—C7	−157.2 (2)	H4A—O1—C28'—C27'	57.8
C9—N7—C8—C7	77.1 (3)	C25—C26—C27'—C28'	22.1 (15)
Fe1—N7—C8—C7	−40.6 (3)	C27—C26—C27'—C28'	−68 (2)
N2—C7—C8—N7	−151.2 (3)	O1—C28'—C27'—C26	−32.6 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···Cl3	0.83 (2)	2.34 (2)	3.136 (3)	160 (4)
O1W—H1B···Cl1	0.83 (2)	2.51 (3)	3.267 (3)	152 (4)
C23—H23···Cl1ⁱ	0.93	2.82	3.516 (3)	133
N2—H2···Cl3ⁱⁱ	0.86 (2)	2.25 (2)	3.070 (3)	159 (3)
N4—H4···O1Wⁱⁱⁱ	0.86 (2)	1.96 (2)	2.795 (4)	162 (3)
N6—H6···O1^iv	0.85 (2)	1.91 (2)	2.741 (4)	163 (3)
C9—H9B···Cl3ⁱⁱⁱ	0.97	2.59	3.523 (3)	162
C3—H3···Cl1^v	0.93	2.83	3.718 (4)	160
C15—H15···Cl2	0.93	2.74	3.466 (3)	136

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+2, y−1/2, −z+3/2; (iii) x, −y+1/2, z+1/2; (iv) x+1, −y+1/2, z+1/2; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[FeCl₂(C₂₄H₂₁N₇)]Cl·C₄H₈O·H₂O
M_r	659.80
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	292
a, b, c (Å)	10.2898 (4), 13.7475 (5), 21.5271 (7)
β (°)	101.614 (1)
V (Å³)	2982.85 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.844, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	17337, 5527, 3999
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.116, 1.00
No. of reflections	5527
No. of parameters	404
No. of restraints	21
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.25

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···Cl3	0.828 (18)	2.34 (2)	3.136 (3)	160 (4)
O1W—H1B···Cl1	0.831 (19)	2.51 (3)	3.267 (3)	152 (4)
N2—H2···Cl3ⁱ	0.859 (18)	2.25 (2)	3.070 (3)	159 (3)
N4—H4···O1Wⁱⁱ	0.862 (18)	1.96 (2)	2.795 (4)	162 (3)
N6—H6···O1ⁱⁱⁱ	0.852 (18)	1.91 (2)	2.741 (4)	163 (3)

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x, −y+1/2, z+1/2; (iii) x+1, −y+1/2, z+1/2.

References

Bruker (2001). SAINT-Plus, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hendriks, M. J., Birker, J. M. W. L., van Rijn, J., Verschoor, G. C. & Reedijk, J. (1982). J. Am. Chem. Soc. 104, 3607–3617. CSD CrossRef CAS Web of Science Google Scholar
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