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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): m828.
Published online 2010 June 23. doi:  10.1107/S1600536810023226
PMCID: PMC3007077

Bis{2-[(2-benzoyl­hydrazin-1-yl­idene)meth­yl]-6-meth­oxy­phenolato}iron(III) chloride monohydrate

Abstract

In the title mononuclear iron(III) complex, [Fe(C15H13N2O3)2]Cl·H2O, the FeIII atom has a distorted octa­hedral geometry and is six-coordinated by four O atoms and two N atoms from two ligands. In the crystal structure, the complex cations, Cl anions and water mol­ecules are connected into a chain along [100] through N—H(...)O, O—H(...)Cl and N—H(...)Cl hydrogen bonds. Two adjacent chains are linked by O—H(...)O hydrogen bonds.

Related literature

For the applications of metal–Schiff base compounds, see: Dilworth (1976 [triangle]); Merchant & Clothia (1970 [triangle]); Pickart et al. (1983 [triangle]). For the ligand synthesis, see: Pouralimardan et al. (2007 [triangle]); Sacconi (1954 [triangle]). For related structures, see: Gao et al. (1998 [triangle]); Monfared et al. (2007 [triangle]); Yu et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m828-scheme1.jpg

Experimental

Crystal data

  • [Fe(C15H13N2O3)2]Cl·H2O
  • M r = 647.86
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m828-efi1.jpg
  • a = 12.7778 (10) Å
  • b = 22.7113 (18) Å
  • c = 10.0604 (7) Å
  • β = 94.542 (1)°
  • V = 2910.4 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.67 mm−1
  • T = 296 K
  • 0.24 × 0.18 × 0.15 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.857, T max = 0.907
  • 14540 measured reflections
  • 5098 independent reflections
  • 3508 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.153
  • S = 0.98
  • 5098 reflections
  • 390 parameters
  • H-atom parameters constrained
  • Δρmax = 0.95 e Å−3
  • Δρmin = −0.48 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT-Plus (Bruker, 2007 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023226/hy2322sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023226/hy2322Isup2.hkl

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

Acknowledgments

We thank the Jilin Environmental Protection Bureau Foundation of China (2007-28) and Changchun University of Science and Technology for financial support.

supplementary crystallographic information

Comment

Studies of acylhydrazone Schiff base and the dependence of their chelation mode with transition metal ions have been of significant interest. On one hand, their metal compounds have been reported to act as enzyme inhibitors (Dilworth, 1976) and are useful due to their pharmacological applications (Merchant & Clothia, 1970). On the other hand, it seems to be a good candidate for catalytic oxidation studies because of their stability to resist oxidation (Pickart et al., 1983). These findings have triggered the exploration of new molecular clusters based on acylhydrazone Schiff base. During the last several years, the crystal structures of metal compounds with 3-methoxysalicylaldehyde benzoylhydrazide have been attracted tremendous interest (Gao et al., 1998; Monfared et al., 2007; Yu et al., 2010). As a continuation of our effort in this system, the preparation and crystal structure of the title Schiff base iron(III) compound are reported here.

The molecular structure of the title compound is illustrated in Fig. 1, which consists of one mononuclear [Fe(C15H13N2O3)2]+ cation, one Cl- anion and one water molecule. The FeIII atom has a distorted octahedral geometry and is six-coordinated by four O atoms and two N atoms from two ligands (Table 1). In one ligand, the strained angle of O1—Fe1—N2 [74.54 (11)°] correlates with the bite angle for the five-membered chelate ring Fe1—O1—C7—N1—N2, and the loose angle of O2—Fe1—N2 [84.74 (11)°] correlates with the six-membered ring Fe1—N2—C8—C9—C10—O2. The axial angle N2—Fe1—N4 [159.46 (12)°] deviates significantly from the ideal 180°. Similar case occurrs for another ligand. In the crystal structure, the complex cations, Cl- anions and water molecules are connected into a chain through N—H···O, O—H···Cl and N—H···Cl hydrogen bonds. Two adjacent chains are linked by O—H···O hydrogen bonds. (Fig. 2 and Table 2).

Experimental

The 3-methoxysalicylaldehyde benzoylhydrazide ligand (H2L) was prepared in a similar manner according to the reported procedures (Pouralimardan et al., 2007; Sacconi, 1954). The title compound was synthesized by adding FeCl3.6H2O (27.0 mg, 0.1 mmol) to a solution of H2L (27.3 mg, 0.10 mmol) in methanol (15 ml). The resulting mixture was stirred for 3 h at room temperature to afford a dark brown solution and then filtered. The filtrate was allowed to stand at room temperature for about three weeks and black crystals were produced at the bottom of the vessel on slow evaporation of methanol.

Refinement

All H atoms were placed in calculated positions and refined using a riding model, with C—H = 0.93 (aromatic), 0.96 (methyl) Å and N—H = 0.86 Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C, N). Water H atoms were located in a difference Fourier map and refined as riding, with O—H = 0.85 Å and Uiso(H) = 1.2Ueq(O).

Figures

Fig. 1.
Molecular structure of the title compound. H atoms are omitted for clarity. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
One-dimensional chain structure in the title compound. Hydrogen bonds are shown as green dashed lines.

Crystal data

[Fe(C15H13N2O3)2]Cl·H2OF(000) = 1340
Mr = 647.86Dx = 1.479 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4767 reflections
a = 12.7778 (10) Åθ = 4.8–51.7°
b = 22.7113 (18) ŵ = 0.67 mm1
c = 10.0604 (7) ÅT = 296 K
β = 94.542 (1)°Block, black
V = 2910.4 (4) Å30.24 × 0.18 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer5098 independent reflections
Radiation source: fine-focus sealed tube3508 reflections with I > 2σ(I)
graphiteRint = 0.052
[var phi] and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.857, Tmax = 0.907k = −27→23
14540 measured reflectionsl = −11→10

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 0.98w = 1/[σ2(Fo2) + (0.0933P)2 + 0.1872P] where P = (Fo2 + 2Fc2)/3
5098 reflections(Δ/σ)max < 0.001
390 parametersΔρmax = 0.95 e Å3
0 restraintsΔρmin = −0.47 e Å3

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

xyzUiso*/Ueq
Fe10.28270 (4)0.56160 (2)0.90592 (5)0.02612 (19)
Cl10.87327 (8)0.66511 (5)0.74420 (12)0.0455 (3)
C10.0861 (3)0.69236 (18)0.5203 (4)0.0376 (10)
H1A0.03960.70240.58320.045*
C20.0804 (4)0.7195 (2)0.3979 (5)0.0449 (12)
H2A0.03050.74870.37870.054*
C30.1472 (4)0.7040 (2)0.3036 (5)0.0511 (13)
H3A0.14160.72270.22110.061*
C40.2219 (4)0.6615 (2)0.3292 (4)0.0433 (11)
H4A0.26590.65080.26400.052*
C50.2313 (3)0.63511 (19)0.4515 (4)0.0350 (10)
H5A0.28370.60730.47030.042*
C60.1631 (3)0.64933 (18)0.5489 (4)0.0307 (9)
C70.1786 (3)0.61984 (17)0.6799 (4)0.0275 (9)
C80.0525 (3)0.58652 (18)0.9627 (4)0.0310 (9)
H8A−0.01290.60230.93590.037*
C90.0651 (3)0.55879 (18)1.0885 (4)0.0294 (9)
C100.1608 (3)0.53399 (17)1.1403 (4)0.0290 (9)
C110.1644 (3)0.50693 (18)1.2666 (4)0.0319 (10)
C120.0756 (3)0.5034 (2)1.3356 (4)0.0397 (11)
H12A0.07860.48441.41770.048*
C13−0.0175 (3)0.5278 (2)1.2842 (4)0.0440 (12)
H13A−0.07660.52561.33220.053*
C14−0.0234 (3)0.5551 (2)1.1631 (4)0.0405 (11)
H14A−0.08670.57161.12940.049*
C150.2726 (4)0.4590 (2)1.4393 (4)0.0500 (13)
H15A0.34460.44781.45940.075*
H15B0.22880.42461.43920.075*
H15C0.25220.48621.50560.075*
C160.5865 (3)0.71820 (18)1.0512 (4)0.0353 (10)
H16A0.63240.69141.01690.042*
C170.6243 (4)0.76907 (19)1.1109 (4)0.0400 (11)
H17A0.69610.77661.11780.048*
C180.5563 (4)0.8090 (2)1.1605 (4)0.0435 (12)
H18A0.58220.84361.20030.052*
C190.4499 (4)0.7979 (2)1.1514 (4)0.0444 (12)
H19A0.40430.82501.18520.053*
C200.4108 (3)0.74682 (18)1.0923 (4)0.0356 (10)
H20A0.33890.73951.08630.043*
C210.4784 (3)0.70675 (17)1.0423 (4)0.0294 (9)
C220.4344 (3)0.65140 (17)0.9850 (4)0.0257 (9)
C230.5028 (3)0.52154 (17)0.8316 (4)0.0257 (9)
H23A0.57350.52970.82440.031*
C240.4618 (3)0.46776 (17)0.7770 (4)0.0267 (9)
C250.3558 (3)0.45109 (17)0.7842 (4)0.0269 (9)
C260.3226 (3)0.39603 (18)0.7277 (4)0.0303 (9)
C270.3928 (3)0.36044 (19)0.6688 (4)0.0351 (10)
H27A0.37030.32460.63190.042*
C280.4968 (3)0.37752 (19)0.6638 (4)0.0366 (10)
H28A0.54340.35270.62460.044*
C290.5312 (3)0.42949 (18)0.7147 (4)0.0327 (10)
H29A0.60080.44040.70910.039*
C300.1794 (4)0.3313 (2)0.6782 (6)0.0551 (14)
H30A0.10630.32800.69280.083*
H30B0.21670.29810.71750.083*
H30C0.18740.33210.58420.083*
N10.1015 (3)0.61943 (14)0.7608 (3)0.0307 (8)
H1B0.04120.63520.73990.037*
N20.1262 (2)0.59143 (14)0.8822 (3)0.0260 (7)
N30.4973 (2)0.61077 (13)0.9384 (3)0.0277 (8)
H3B0.56400.61580.93780.033*
N40.4475 (2)0.55953 (13)0.8906 (3)0.0231 (7)
O10.2638 (2)0.59602 (12)0.7150 (3)0.0307 (6)
O1W0.7122 (2)0.60423 (13)0.9294 (3)0.0421 (8)
H1WA0.73680.57190.96110.050*
H1WB0.74340.62400.87250.050*
O20.2468 (2)0.53545 (13)1.0763 (3)0.0346 (7)
O30.2611 (2)0.48627 (13)1.3112 (3)0.0396 (7)
O40.3375 (2)0.64162 (12)0.9791 (3)0.0318 (7)
O50.2873 (2)0.48311 (12)0.8409 (3)0.0323 (7)
O60.2204 (2)0.38391 (13)0.7375 (3)0.0423 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0196 (3)0.0345 (3)0.0245 (3)0.0041 (2)0.0039 (2)0.0024 (3)
Cl10.0289 (6)0.0524 (7)0.0550 (8)0.0074 (5)0.0009 (5)0.0078 (6)
C10.036 (3)0.040 (3)0.036 (3)0.001 (2)−0.0045 (19)0.007 (2)
C20.045 (3)0.045 (3)0.043 (3)0.001 (2)−0.008 (2)0.013 (2)
C30.055 (3)0.062 (3)0.034 (3)−0.011 (3)−0.010 (2)0.024 (2)
C40.046 (3)0.055 (3)0.029 (3)−0.001 (2)0.001 (2)0.008 (2)
C50.036 (2)0.042 (3)0.027 (2)0.001 (2)0.0000 (19)0.002 (2)
C60.029 (2)0.036 (2)0.027 (2)−0.0047 (18)−0.0044 (18)0.0020 (18)
C70.028 (2)0.028 (2)0.026 (2)−0.0035 (17)0.0018 (17)−0.0018 (17)
C80.026 (2)0.041 (2)0.026 (2)0.0031 (18)0.0046 (18)0.0017 (19)
C90.024 (2)0.038 (2)0.026 (2)0.0022 (18)0.0032 (17)−0.0015 (19)
C100.028 (2)0.032 (2)0.028 (2)0.0005 (17)0.0064 (17)−0.0040 (18)
C110.036 (2)0.035 (2)0.025 (2)−0.0016 (19)0.0011 (18)−0.0016 (19)
C120.037 (3)0.056 (3)0.026 (2)−0.003 (2)0.0081 (19)0.001 (2)
C130.034 (3)0.068 (3)0.032 (3)−0.002 (2)0.013 (2)0.005 (2)
C140.030 (2)0.058 (3)0.034 (3)0.006 (2)0.0046 (19)0.007 (2)
C150.056 (3)0.068 (3)0.026 (2)0.006 (3)0.003 (2)0.017 (2)
C160.033 (2)0.036 (2)0.037 (3)0.0015 (19)0.0023 (19)−0.001 (2)
C170.043 (3)0.039 (3)0.036 (3)−0.005 (2)−0.005 (2)0.002 (2)
C180.062 (3)0.039 (3)0.028 (2)−0.006 (2)−0.003 (2)−0.009 (2)
C190.052 (3)0.041 (3)0.040 (3)0.010 (2)0.003 (2)−0.009 (2)
C200.040 (3)0.038 (2)0.029 (2)0.006 (2)0.0011 (19)−0.0023 (19)
C210.032 (2)0.033 (2)0.022 (2)−0.0003 (18)−0.0045 (17)0.0024 (18)
C220.023 (2)0.033 (2)0.021 (2)0.0052 (17)−0.0003 (16)0.0050 (17)
C230.020 (2)0.037 (2)0.020 (2)0.0047 (17)0.0027 (16)0.0028 (17)
C240.022 (2)0.037 (2)0.020 (2)0.0021 (17)−0.0017 (16)0.0021 (18)
C250.028 (2)0.033 (2)0.019 (2)0.0039 (17)0.0007 (17)0.0034 (17)
C260.027 (2)0.037 (2)0.027 (2)−0.0001 (18)−0.0022 (17)0.0054 (18)
C270.043 (3)0.035 (2)0.027 (2)0.002 (2)−0.0001 (19)−0.0036 (19)
C280.033 (2)0.043 (3)0.034 (2)0.008 (2)0.0037 (19)−0.010 (2)
C290.025 (2)0.041 (3)0.032 (2)0.0027 (18)0.0034 (18)−0.0056 (19)
C300.041 (3)0.047 (3)0.077 (4)−0.013 (2)−0.001 (3)−0.012 (3)
N10.0245 (18)0.040 (2)0.0274 (19)0.0083 (15)0.0023 (14)0.0098 (15)
N20.0231 (17)0.0344 (19)0.0201 (17)0.0038 (14)−0.0001 (14)0.0063 (14)
N30.0231 (17)0.0315 (18)0.0281 (19)−0.0025 (14)0.0002 (14)−0.0003 (15)
N40.0208 (16)0.0286 (17)0.0197 (16)0.0011 (14)−0.0008 (13)−0.0002 (14)
O10.0250 (15)0.0424 (17)0.0251 (15)0.0053 (13)0.0053 (12)0.0069 (13)
O1W0.0332 (17)0.0456 (19)0.0476 (19)0.0050 (14)0.0044 (14)0.0046 (15)
O20.0249 (15)0.0553 (19)0.0242 (15)0.0088 (13)0.0043 (12)0.0116 (13)
O30.0346 (17)0.059 (2)0.0248 (16)0.0076 (15)0.0022 (13)0.0145 (14)
O40.0279 (16)0.0359 (16)0.0318 (16)0.0046 (12)0.0033 (12)−0.0048 (13)
O50.0235 (15)0.0342 (16)0.0399 (17)0.0001 (12)0.0073 (12)−0.0046 (13)
O60.0303 (17)0.0440 (18)0.053 (2)−0.0081 (14)0.0050 (14)−0.0108 (15)

Geometric parameters (Å, °)

Fe1—O12.070 (3)C16—C171.372 (6)
Fe1—O21.904 (3)C16—C211.402 (6)
Fe1—O42.062 (3)C16—H16A0.9300
Fe1—O51.901 (3)C17—C181.377 (6)
Fe1—N22.106 (3)C17—H17A0.9300
Fe1—N42.124 (3)C18—C191.379 (7)
C1—C21.373 (6)C18—H18A0.9300
C1—C61.401 (6)C19—C201.379 (6)
C1—H1A0.9300C19—H19A0.9300
C2—C31.372 (7)C20—C211.377 (5)
C2—H2A0.9300C20—H20A0.9300
C3—C41.367 (6)C21—C221.476 (5)
C3—H3A0.9300C22—O41.254 (4)
C4—C51.365 (6)C22—N31.334 (5)
C4—H4A0.9300C23—N41.289 (5)
C5—C61.399 (6)C23—C241.422 (5)
C5—H5A0.9300C23—H23A0.9300
C6—C71.478 (5)C24—C251.413 (5)
C7—O11.241 (5)C24—C291.422 (5)
C7—N11.328 (5)C25—O51.303 (4)
C8—N21.294 (4)C25—C261.425 (5)
C8—C91.411 (5)C26—O61.346 (5)
C8—H8A0.9300C26—C271.375 (6)
C9—C101.408 (5)C27—C281.389 (6)
C9—C141.409 (5)C27—H27A0.9300
C10—O21.317 (4)C28—C291.347 (6)
C10—C111.409 (5)C28—H28A0.9300
C11—O31.364 (5)C29—H29A0.9300
C11—C121.379 (5)C30—O61.417 (5)
C12—C131.375 (6)C30—H30A0.9600
C12—H12A0.9300C30—H30B0.9600
C13—C141.364 (6)C30—H30C0.9600
C13—H13A0.9300N1—N21.391 (4)
C14—H14A0.9300N1—H1B0.8600
C15—O31.428 (5)N3—N41.394 (4)
C15—H15A0.9600N3—H3B0.8600
C15—H15B0.9600O1W—H1WA0.8500
C15—H15C0.9600O1W—H1WB0.8502
O5—Fe1—O291.94 (12)C21—C16—H16A120.1
O5—Fe1—O4158.43 (11)C16—C17—C18120.2 (4)
O2—Fe1—O493.00 (12)C16—C17—H17A119.9
O5—Fe1—O192.26 (11)C18—C17—H17A119.9
O2—Fe1—O1159.12 (11)C17—C18—C19120.2 (4)
O4—Fe1—O190.57 (11)C17—C18—H18A119.9
O5—Fe1—N2108.53 (12)C19—C18—H18A119.9
O2—Fe1—N284.74 (11)C18—C19—C20120.3 (4)
O4—Fe1—N292.83 (11)C18—C19—H19A119.9
O1—Fe1—N274.54 (11)C20—C19—H19A119.9
O5—Fe1—N484.04 (11)C21—C20—C19119.8 (4)
O2—Fe1—N4111.65 (11)C21—C20—H20A120.1
O4—Fe1—N474.63 (11)C19—C20—H20A120.1
O1—Fe1—N489.13 (11)C20—C21—C16119.9 (4)
N2—Fe1—N4159.46 (12)C20—C21—C22118.4 (4)
C2—C1—C6118.9 (4)C16—C21—C22121.7 (4)
C2—C1—H1A120.5O4—C22—N3118.8 (4)
C6—C1—H1A120.5O4—C22—C21120.9 (3)
C3—C2—C1120.9 (4)N3—C22—C21120.3 (3)
C3—C2—H2A119.6N4—C23—C24123.6 (3)
C1—C2—H2A119.6N4—C23—H23A118.2
C4—C3—C2121.0 (4)C24—C23—H23A118.2
C4—C3—H3A119.5C25—C24—C29119.5 (4)
C2—C3—H3A119.5C25—C24—C23122.4 (3)
C5—C4—C3119.3 (4)C29—C24—C23118.1 (3)
C5—C4—H4A120.3O5—C25—C24123.5 (4)
C3—C4—H4A120.3O5—C25—C26118.4 (3)
C4—C5—C6120.9 (4)C24—C25—C26118.1 (3)
C4—C5—H5A119.5O6—C26—C27125.5 (4)
C6—C5—H5A119.5O6—C26—C25114.2 (3)
C5—C6—C1118.9 (4)C27—C26—C25120.3 (4)
C5—C6—C7118.2 (4)C26—C27—C28120.6 (4)
C1—C6—C7122.8 (4)C26—C27—H27A119.7
O1—C7—N1120.0 (4)C28—C27—H27A119.7
O1—C7—C6120.3 (3)C29—C28—C27121.0 (4)
N1—C7—C6119.8 (4)C29—C28—H28A119.5
N2—C8—C9124.2 (4)C27—C28—H28A119.5
N2—C8—H8A117.9C28—C29—C24120.5 (4)
C9—C8—H8A117.9C28—C29—H29A119.8
C10—C9—C14119.3 (4)C24—C29—H29A119.8
C10—C9—C8123.0 (3)O6—C30—H30A109.5
C14—C9—C8117.7 (4)O6—C30—H30B109.5
O2—C10—C9122.9 (3)H30A—C30—H30B109.5
O2—C10—C11118.8 (4)O6—C30—H30C109.5
C9—C10—C11118.3 (3)H30A—C30—H30C109.5
O3—C11—C12125.1 (4)H30B—C30—H30C109.5
O3—C11—C10114.3 (3)C7—N1—N2114.4 (3)
C12—C11—C10120.6 (4)C7—N1—H1B122.8
C13—C12—C11120.6 (4)N2—N1—H1B122.8
C13—C12—H12A119.7C8—N2—N1117.5 (3)
C11—C12—H12A119.7C8—N2—Fe1129.2 (3)
C14—C13—C12120.3 (4)N1—N2—Fe1113.2 (2)
C14—C13—H13A119.8C22—N3—N4115.3 (3)
C12—C13—H13A119.8C22—N3—H3B122.4
C13—C14—C9120.8 (4)N4—N3—H3B122.4
C13—C14—H14A119.6C23—N4—N3117.7 (3)
C9—C14—H14A119.6C23—N4—Fe1129.1 (3)
O3—C15—H15A109.5N3—N4—Fe1112.6 (2)
O3—C15—H15B109.5C7—O1—Fe1117.7 (2)
H15A—C15—H15B109.5H1WA—O1W—H1WB121.9
O3—C15—H15C109.5C10—O2—Fe1135.8 (3)
H15A—C15—H15C109.5C11—O3—C15118.2 (3)
H15B—C15—H15C109.5C22—O4—Fe1118.6 (2)
C17—C16—C21119.7 (4)C25—O5—Fe1135.6 (2)
C17—C16—H16A120.1C26—O6—C30118.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1B···Cl1i0.862.253.087 (3)163
N3—H3B···O1W0.861.922.759 (4)164
O1W—H1WA···O5ii0.852.393.045 (4)134
O1W—H1WB···Cl10.852.373.198 (3)163

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2322).

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