Chlorido{N,N′-o-phenyl­ene-[6,6′-ethyl­enebis(pyridine-2-carboxamide)]}iron(III)

Yang, L.; Tang, B.

doi:10.1107/S1600536808041354

Chlorido{N,N′-o-phenylene-[6,6′-ethylenebis(pyridine-2-carboxamide)]}iron(III)

In the title compound, [Fe(C₂₀H₁₄N₄O₂)Cl], the Fe^III ion is in a distorted square-pyramidal environment, with two pyridine and two deprotonated amide N atoms in the basal plane and the Cl ion in the apical position. The Fe^III ion is displaced from the basal plane of the square- pyramid towards the apical Cl atom by 0.2942 (4) Å. The molecules are linked into a three-dimensional network by C—H

Cl and C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808041354/ci2736sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808041354/ci2736Isup2.hkl Contains datablock I

CCDC reference: 679447

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.040
wR factor = 0.126
Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   296.000
            Value of melting point given =     0.000
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.90

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.904
            Tmax scaled      0.904 Tmin scaled      0.703

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The chemistry of macrocyclic complexes has attracted the interest of both inorganic and bioinorganic chemists in recent years. Iron(III) complexes are involved in numerous biological redox reactions performed by metalloenzymes (Momenteau et al., 1994). As part of our studies on catalysis by N4 non-porphyrin complexes (Liu et al., 2006; Yang et al., 2007), we report here the crystal structure of a iron(III) complex with 1,2-[bis(6'-pyridine-2'-carboxamido)-ethane]benzene.

As shown in Fig.1, the complex has a five-coordinate structure with two pyridine and two deprotonated amide N atoms in the basal plane while the Cl ion is bonded to the Fe^III center in the apical position. The geometry around the Fe^III ion is approximately square-pyramidal. The Fe—N(amide) distances are shorter than the Fe—N(pyridine) distances (Table 1), both of which are shorter than the Fe—N distances found in the non-ring related Fe—N4 complexes such as [NEt₄][Fe(bbpc)Cl₂][H₂bbpc is N,N'-(4,5-dichloro-o-phenylene)bis(4-tertbutylpyridine-2-carboxamide)] (Xu et al., 2007). The Fe—Cl distance of 2.3080 (8) Å is slightly shorter than that observed in [Fe(bbpc)Cl₂](Et₄N) (2.3299 (9) Å and 2.3880 (9) Å), while it is longer than that in [FeCl(meso-NH₂-octaethylporphyrin)] (2.2596 (8) Å, Sankar et al., 2004).

In the crystalline state, the molecules are linked into a three-dimensional network by C—H···Cl and C—H···O hydrogen bonds (Table 2).

Related literature top

For general background, see: Liu et al. (2006); Yang et al. (2007); Momenteau et al. (1994). For related structures, see: Rath et al. (2004); Xu et al. (2007).

Experimental top

1,2-[Bis(6'-pyridine-2'carboxamido)-ethane]benzene (132 mg, 0.38 mmol) and sodium acetate (80 mg, 0.76 mmol) were added to a stirred solution of FeCl₃.6H₂O (244 mg, 0.9 mmol) in CH₃OH (20 ml). The colour of the mixture turned green almost immediately. The mixture was refluxed for 3 h and dark green microcrystals appeared. They were collected by filtration, washed with methanol, and air-dried. (123 mg, yield 75%). Single crystals suitable for X-ray diffraction were grown via diffusion of Et₂O into a DMF solution of the complex. Selected IR data (KBr, cm^-1):ν=1629 (C=O), 1602 (C—N), 1572, 1346, 1287, 1142, 1083, 1081, 762. MS (FAB): 398.3([Fe(bpeb)]⁺).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

Chlorido{N,N'-o-phenylene-[6,6'-ethylenebis(pyridine-2-carboxamide)]}iron(III) top

Crystal data top

[Fe(C₂₀H₁₄N₄O₂)Cl]	F(000) = 884
M_r = 433.65	D_x = 1.600 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9989 reflections
a = 11.8532 (2) Å	θ = 2.2–27.4°
b = 8.2028 (1) Å	µ = 1.01 mm⁻¹
c = 19.3507 (3) Å	T = 296 K
β = 106.889 (1)°	Plate, black
V = 1800.31 (5) Å³	0.44 × 0.16 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4142 independent reflections
Radiation source: fine-focus sealed tube	3415 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)	h = −15→15
T_min = 0.778, T_max = 1.000	k = −10→10
24687 measured reflections	l = −25→25

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0642P)² + 2.4383P] where P = (F_o² + 2F_c²)/3
4142 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Fe(C₂₀H₁₄N₄O₂)Cl]	V = 1800.31 (5) Å³
M_r = 433.65	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8532 (2) Å	µ = 1.01 mm⁻¹
b = 8.2028 (1) Å	T = 296 K
c = 19.3507 (3) Å	0.44 × 0.16 × 0.10 mm
β = 106.889 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4142 independent reflections
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)	3415 reflections with I > 2σ(I)
T_min = 0.778, T_max = 1.000	R_int = 0.041
24687 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.01	Δρ_max = 0.62 e Å⁻³
4142 reflections	Δρ_min = −0.43 e Å⁻³
253 parameters

Special details top

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
Fe1	0.45008 (3)	0.56516 (5)	0.62759 (2)	0.02844 (13)
Cl1	0.49959 (7)	0.48979 (10)	0.74759 (4)	0.0423 (2)
O1	0.1136 (2)	0.6292 (4)	0.61432 (18)	0.0676 (8)
O2	0.5587 (2)	0.2335 (3)	0.51016 (14)	0.0529 (6)
N1	0.2870 (2)	0.5301 (3)	0.59827 (14)	0.0352 (5)
N2	0.4003 (2)	0.7937 (3)	0.64688 (12)	0.0321 (5)
N3	0.6194 (2)	0.5763 (3)	0.62630 (12)	0.0298 (5)
N4	0.44925 (19)	0.3762 (3)	0.57162 (12)	0.0305 (5)
C1	0.2181 (3)	0.6411 (4)	0.61888 (17)	0.0399 (7)
C2	0.2867 (3)	0.7921 (4)	0.64770 (16)	0.0373 (6)
C3	0.2337 (3)	0.9212 (4)	0.67153 (19)	0.0509 (9)
H3A	0.1555	0.9156	0.6719	0.061*
C4	0.3014 (4)	1.0606 (5)	0.6950 (2)	0.0564 (10)
H4A	0.2696	1.1495	0.7127	0.068*
C5	0.4145 (4)	1.0649 (4)	0.69173 (18)	0.0483 (8)
H5A	0.4594	1.1585	0.7062	0.058*
C6	0.4643 (3)	0.9306 (4)	0.66690 (16)	0.0377 (7)
C7	0.5853 (3)	0.9393 (4)	0.65875 (18)	0.0443 (7)
H7A	0.6159	1.0483	0.6716	0.053*
H7B	0.5800	0.9222	0.6083	0.053*
C8	0.6751 (3)	0.8146 (4)	0.70492 (17)	0.0418 (7)
H8A	0.7468	0.8722	0.7301	0.050*
H8B	0.6425	0.7683	0.7411	0.050*
C9	0.7061 (2)	0.6787 (4)	0.66208 (15)	0.0352 (6)
C10	0.8207 (3)	0.6559 (4)	0.65877 (18)	0.0453 (8)
H10A	0.8794	0.7287	0.6824	0.054*
C11	0.8485 (3)	0.5277 (5)	0.62112 (19)	0.0479 (8)
H11A	0.9255	0.5124	0.6195	0.057*
C12	0.7599 (3)	0.4217 (4)	0.58564 (17)	0.0413 (7)
H12A	0.7760	0.3331	0.5600	0.050*
C13	0.6471 (2)	0.4504 (3)	0.58911 (15)	0.0314 (6)
C14	0.5471 (2)	0.3397 (4)	0.55255 (15)	0.0333 (6)
C15	0.2484 (2)	0.3809 (4)	0.56301 (16)	0.0348 (6)
C16	0.1338 (3)	0.3196 (4)	0.5414 (2)	0.0499 (8)
H16A	0.0724	0.3773	0.5509	0.060*
C17	0.1128 (3)	0.1721 (5)	0.5056 (2)	0.0590 (10)
H17A	0.0364	0.1311	0.4905	0.071*
C18	0.2030 (3)	0.0846 (4)	0.4919 (2)	0.0547 (9)
H18A	0.1870	−0.0153	0.4683	0.066*
C19	0.3178 (3)	0.1438 (4)	0.51280 (16)	0.0414 (7)
H19A	0.3789	0.0840	0.5041	0.050*
C20	0.3393 (2)	0.2947 (3)	0.54712 (15)	0.0328 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0262 (2)	0.0225 (2)	0.0375 (2)	−0.00026 (14)	0.01073 (15)	−0.00375 (15)
Cl1	0.0483 (4)	0.0381 (4)	0.0427 (4)	0.0044 (3)	0.0169 (3)	0.0083 (3)
O1	0.0352 (13)	0.0650 (18)	0.109 (2)	0.0042 (12)	0.0307 (14)	−0.0117 (17)
O2	0.0472 (13)	0.0475 (14)	0.0671 (15)	0.0005 (11)	0.0215 (11)	−0.0268 (12)
N1	0.0278 (11)	0.0299 (13)	0.0484 (14)	0.0000 (9)	0.0119 (10)	−0.0014 (10)
N2	0.0410 (13)	0.0221 (11)	0.0345 (12)	0.0034 (10)	0.0132 (10)	−0.0013 (9)
N3	0.0287 (11)	0.0274 (12)	0.0334 (11)	−0.0026 (9)	0.0091 (9)	−0.0020 (9)
N4	0.0301 (11)	0.0237 (11)	0.0370 (12)	−0.0025 (9)	0.0088 (9)	−0.0049 (9)
C1	0.0337 (15)	0.0377 (17)	0.0515 (17)	0.0065 (12)	0.0175 (13)	0.0020 (14)
C2	0.0424 (16)	0.0333 (15)	0.0396 (15)	0.0099 (12)	0.0173 (12)	0.0021 (12)
C3	0.058 (2)	0.047 (2)	0.055 (2)	0.0213 (17)	0.0282 (17)	0.0042 (16)
C4	0.083 (3)	0.0406 (19)	0.0494 (19)	0.0225 (19)	0.0254 (18)	−0.0016 (15)
C5	0.076 (2)	0.0272 (15)	0.0401 (16)	0.0053 (15)	0.0136 (16)	−0.0027 (13)
C6	0.0547 (18)	0.0249 (14)	0.0325 (14)	0.0017 (13)	0.0108 (12)	0.0010 (11)
C7	0.0553 (19)	0.0264 (15)	0.0517 (18)	−0.0103 (13)	0.0166 (15)	−0.0024 (13)
C8	0.0421 (16)	0.0388 (17)	0.0411 (16)	−0.0095 (13)	0.0069 (13)	−0.0082 (13)
C9	0.0322 (14)	0.0346 (15)	0.0365 (14)	−0.0063 (12)	0.0066 (11)	−0.0002 (12)
C10	0.0314 (15)	0.051 (2)	0.0500 (18)	−0.0110 (14)	0.0058 (13)	0.0020 (15)
C11	0.0270 (14)	0.063 (2)	0.0540 (19)	0.0007 (14)	0.0126 (13)	0.0059 (17)
C12	0.0330 (15)	0.0472 (19)	0.0462 (17)	0.0054 (13)	0.0154 (13)	0.0001 (14)
C13	0.0311 (13)	0.0311 (14)	0.0321 (13)	0.0019 (11)	0.0092 (10)	0.0020 (11)
C14	0.0339 (14)	0.0296 (14)	0.0360 (14)	0.0024 (11)	0.0094 (11)	−0.0030 (11)
C15	0.0318 (14)	0.0287 (14)	0.0423 (15)	−0.0045 (11)	0.0084 (11)	0.0036 (12)
C16	0.0325 (16)	0.0450 (19)	0.070 (2)	−0.0058 (14)	0.0115 (15)	0.0041 (17)
C17	0.0431 (19)	0.047 (2)	0.079 (3)	−0.0221 (16)	0.0051 (17)	0.0039 (19)
C18	0.063 (2)	0.0346 (18)	0.059 (2)	−0.0211 (16)	0.0073 (17)	−0.0051 (15)
C19	0.0493 (18)	0.0317 (16)	0.0420 (16)	−0.0082 (13)	0.0114 (13)	−0.0036 (13)
C20	0.0326 (14)	0.0281 (14)	0.0360 (14)	−0.0047 (11)	0.0073 (11)	0.0012 (11)

Geometric parameters (Å, º) top

Fe1—N1	1.871 (2)	C7—C8	1.557 (5)
Fe1—N4	1.889 (2)	C7—H7A	0.97
Fe1—N3	2.016 (2)	C7—H7B	0.97
Fe1—N2	2.032 (2)	C8—C9	1.497 (4)
Fe1—Cl1	2.3080 (8)	C8—H8A	0.97
O1—C1	1.220 (4)	C8—H8B	0.97
O2—C14	1.231 (3)	C9—C10	1.392 (4)
N1—C1	1.358 (4)	C10—C11	1.373 (5)
N1—C15	1.412 (4)	C10—H10A	0.93
N2—C6	1.348 (4)	C11—C12	1.383 (5)
N2—C2	1.350 (4)	C11—H11A	0.93
N3—C9	1.352 (4)	C12—C13	1.378 (4)
N3—C13	1.353 (4)	C12—H12A	0.93
N4—C14	1.349 (4)	C13—C14	1.498 (4)
N4—C20	1.418 (3)	C15—C16	1.394 (4)
C1—C2	1.498 (5)	C15—C20	1.396 (4)
C2—C3	1.378 (4)	C16—C17	1.380 (5)
C3—C4	1.395 (6)	C16—H16A	0.93
C3—H3A	0.93	C17—C18	1.376 (6)
C4—C5	1.361 (6)	C17—H17A	0.93
C4—H4A	0.93	C18—C19	1.390 (5)
C5—C6	1.399 (4)	C18—H18A	0.93
C5—H5A	0.93	C19—C20	1.392 (4)
C6—C7	1.490 (5)	C19—H19A	0.93

N1—Fe1—N4	82.38 (10)	C8—C7—H7B	108.5
N1—Fe1—N3	161.28 (10)	H7A—C7—H7B	107.5
N4—Fe1—N3	82.51 (9)	C9—C8—C7	114.1 (3)
N1—Fe1—N2	82.39 (10)	C9—C8—H8A	108.7
N4—Fe1—N2	155.32 (10)	C7—C8—H8A	108.7
N3—Fe1—N2	107.69 (10)	C9—C8—H8B	108.7
N1—Fe1—Cl1	101.67 (8)	C7—C8—H8B	108.7
N4—Fe1—Cl1	108.32 (8)	H8A—C8—H8B	107.6
N3—Fe1—Cl1	93.53 (7)	N3—C9—C10	120.1 (3)
N2—Fe1—Cl1	93.71 (7)	N3—C9—C8	118.3 (3)
C1—N1—C15	125.8 (3)	C10—C9—C8	121.7 (3)
C1—N1—Fe1	117.7 (2)	C11—C10—C9	121.0 (3)
C15—N1—Fe1	116.19 (19)	C11—C10—H10A	119.5
C6—N2—C2	119.0 (3)	C9—C10—H10A	119.5
C6—N2—Fe1	130.7 (2)	C10—C11—C12	118.7 (3)
C2—N2—Fe1	109.69 (19)	C10—C11—H11A	120.6
C9—N3—C13	118.7 (2)	C12—C11—H11A	120.6
C9—N3—Fe1	129.3 (2)	C13—C12—C11	118.4 (3)
C13—N3—Fe1	111.65 (18)	C13—C12—H12A	120.8
C14—N4—C20	125.7 (2)	C11—C12—H12A	120.8
C14—N4—Fe1	118.49 (18)	N3—C13—C12	123.1 (3)
C20—N4—Fe1	115.45 (18)	N3—C13—C14	115.6 (2)
O1—C1—N1	127.6 (3)	C12—C13—C14	121.3 (3)
O1—C1—C2	121.5 (3)	O2—C14—N4	127.6 (3)
N1—C1—C2	110.8 (2)	O2—C14—C13	121.2 (3)
N2—C2—C3	123.4 (3)	N4—C14—C13	111.2 (2)
N2—C2—C1	116.0 (2)	C16—C15—C20	119.9 (3)
C3—C2—C1	120.6 (3)	C16—C15—N1	127.5 (3)
C2—C3—C4	117.6 (3)	C20—C15—N1	112.5 (2)
C2—C3—H3A	121.2	C17—C16—C15	119.0 (3)
C4—C3—H3A	121.2	C17—C16—H16A	120.5
C5—C4—C3	119.1 (3)	C15—C16—H16A	120.5
C5—C4—H4A	120.4	C18—C17—C16	121.1 (3)
C3—C4—H4A	120.4	C18—C17—H17A	119.4
C4—C5—C6	121.0 (3)	C16—C17—H17A	119.4
C4—C5—H5A	119.5	C17—C18—C19	120.8 (3)
C6—C5—H5A	119.5	C17—C18—H18A	119.6
N2—C6—C5	119.8 (3)	C19—C18—H18A	119.6
N2—C6—C7	119.2 (3)	C18—C19—C20	118.5 (3)
C5—C6—C7	120.9 (3)	C18—C19—H19A	120.7
C6—C7—C8	115.3 (3)	C20—C19—H19A	120.7
C6—C7—H7A	108.5	C19—C20—C15	120.6 (3)
C8—C7—H7A	108.5	C19—C20—N4	127.0 (3)
C6—C7—H7B	108.5	C15—C20—N4	112.4 (2)

N4—Fe1—N1—C1	−176.9 (2)	C2—N2—C6—C7	−173.6 (3)
N3—Fe1—N1—C1	−140.5 (3)	Fe1—N2—C6—C7	16.6 (4)
N2—Fe1—N1—C1	−16.3 (2)	C4—C5—C6—N2	−1.0 (5)
Cl1—Fe1—N1—C1	75.9 (2)	C4—C5—C6—C7	175.9 (3)
N4—Fe1—N1—C15	9.6 (2)	N2—C6—C7—C8	−63.1 (4)
N3—Fe1—N1—C15	46.0 (4)	C5—C6—C7—C8	119.9 (3)
N2—Fe1—N1—C15	170.1 (2)	C6—C7—C8—C9	107.4 (3)
Cl1—Fe1—N1—C15	−97.6 (2)	C13—N3—C9—C10	1.6 (4)
N1—Fe1—N2—C6	−173.7 (3)	Fe1—N3—C9—C10	174.0 (2)
N4—Fe1—N2—C6	−121.4 (3)	C13—N3—C9—C8	−178.2 (3)
N3—Fe1—N2—C6	−9.9 (3)	Fe1—N3—C9—C8	−5.7 (4)
Cl1—Fe1—N2—C6	85.0 (2)	C7—C8—C9—N3	−62.5 (4)
N1—Fe1—N2—C2	15.76 (19)	C7—C8—C9—C10	117.7 (3)
N4—Fe1—N2—C2	68.1 (3)	N3—C9—C10—C11	−1.8 (5)
N3—Fe1—N2—C2	179.57 (18)	C8—C9—C10—C11	177.9 (3)
Cl1—Fe1—N2—C2	−85.53 (19)	C9—C10—C11—C12	0.7 (5)
N1—Fe1—N3—C9	150.2 (3)	C10—C11—C12—C13	0.6 (5)
N4—Fe1—N3—C9	−173.5 (3)	C9—N3—C13—C12	−0.3 (4)
N2—Fe1—N3—C9	29.6 (3)	Fe1—N3—C13—C12	−174.0 (2)
Cl1—Fe1—N3—C9	−65.4 (2)	C9—N3—C13—C14	178.4 (2)
N1—Fe1—N3—C13	−37.0 (4)	Fe1—N3—C13—C14	4.7 (3)
N4—Fe1—N3—C13	−0.60 (19)	C11—C12—C13—N3	−0.8 (5)
N2—Fe1—N3—C13	−157.53 (18)	C11—C12—C13—C14	−179.4 (3)
Cl1—Fe1—N3—C13	107.44 (18)	C20—N4—C14—O2	1.6 (5)
N1—Fe1—N4—C14	164.8 (2)	Fe1—N4—C14—O2	−171.3 (3)
N3—Fe1—N4—C14	−4.1 (2)	C20—N4—C14—C13	−179.7 (2)
N2—Fe1—N4—C14	112.5 (3)	Fe1—N4—C14—C13	7.5 (3)
Cl1—Fe1—N4—C14	−95.4 (2)	N3—C13—C14—O2	171.0 (3)
N1—Fe1—N4—C20	−8.8 (2)	C12—C13—C14—O2	−10.3 (4)
N3—Fe1—N4—C20	−177.7 (2)	N3—C13—C14—N4	−7.8 (4)
N2—Fe1—N4—C20	−61.1 (3)	C12—C13—C14—N4	170.9 (3)
Cl1—Fe1—N4—C20	91.03 (19)	C1—N1—C15—C16	1.3 (5)
C15—N1—C1—O1	4.1 (6)	Fe1—N1—C15—C16	174.3 (3)
Fe1—N1—C1—O1	−168.8 (3)	C1—N1—C15—C20	178.5 (3)
C15—N1—C1—C2	−174.1 (3)	Fe1—N1—C15—C20	−8.6 (3)
Fe1—N1—C1—C2	13.1 (3)	C20—C15—C16—C17	1.3 (5)
C6—N2—C2—C3	−3.4 (4)	N1—C15—C16—C17	178.3 (3)
Fe1—N2—C2—C3	168.4 (3)	C15—C16—C17—C18	0.7 (6)
C6—N2—C2—C1	175.0 (3)	C16—C17—C18—C19	−1.0 (6)
Fe1—N2—C2—C1	−13.2 (3)	C17—C18—C19—C20	−0.8 (5)
O1—C1—C2—N2	−176.9 (3)	C18—C19—C20—C15	2.8 (5)
N1—C1—C2—N2	1.3 (4)	C18—C19—C20—N4	−179.2 (3)
O1—C1—C2—C3	1.5 (5)	C16—C15—C20—C19	−3.1 (5)
N1—C1—C2—C3	179.8 (3)	N1—C15—C20—C19	179.5 (3)
N2—C2—C3—C4	0.8 (5)	C16—C15—C20—N4	178.7 (3)
C1—C2—C3—C4	−177.5 (3)	N1—C15—C20—N4	1.3 (4)
C2—C3—C4—C5	1.6 (5)	C14—N4—C20—C19	15.3 (5)
C3—C4—C5—C6	−1.5 (5)	Fe1—N4—C20—C19	−171.7 (2)
C2—N2—C6—C5	3.4 (4)	C14—N4—C20—C15	−166.7 (3)
Fe1—N2—C6—C5	−166.4 (2)	Fe1—N4—C20—C15	6.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cl1ⁱ	0.93	2.80	3.595 (4)	144
C10—H10A···Cl1ⁱⁱ	0.93	2.71	3.617 (3)	165
C11—H11A···O1ⁱⁱⁱ	0.93	2.46	3.290 (5)	149

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

Experimental details

Crystal data
Chemical formula	[Fe(C₂₀H₁₄N₄O₂)Cl]
M_r	433.65
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.8532 (2), 8.2028 (1), 19.3507 (3)
β (°)	106.889 (1)
V (Å³)	1800.31 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.44 × 0.16 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS, Sheldrick, 1996)
T_min, T_max	0.778, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	24687, 4142, 3415
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.126, 1.01
No. of reflections	4142
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.43

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Fe1—N1	1.871 (2)	Fe1—N2	2.032 (2)
Fe1—N4	1.889 (2)	Fe1—Cl1	2.3080 (8)
Fe1—N3	2.016 (2)