[Benzoyl­acetone (4-methoxy­benzoyl)­hydrazonato-κ³O,N²,O′]­di­chloro­iron(III)

In the title complex, [Fe(C₁₈H₁₇N₂O₃)Cl₂], the Fe^III species has a distorted trigonal–bipyramidal geometry, defined by two O atoms and one N atom from the tridentate hydrazone ligand and two Cl⁻ anions. A hydrogen-bonded dimer is formed via two N—H...Cl intermolecular hydrogen bonds across a center of inversion.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.100
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   Cl2     ..       5.83 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         O2
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.37

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

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

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

[Benzoylacetone (4-methoxybenzoyl)hydrazonato-κ³O,N²,O']dichloroiron(III)

Crystal data

[Fe(C18H17N2O3)Cl2]	F(000) = 892
Mr = 436.09	Dx = 1.533 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17064 reflections
a = 7.5958 (3) Å	θ = 3.1–27.5°
b = 13.4330 (3) Å	µ = 1.10 mm^−1
c = 18.5880 (4) Å	T = 293 K
β = 94.973 (3)°	Prism, black
V = 1889.48 (10) Å^3	0.39 × 0.26 × 0.18 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	4303 independent reflections
Radiation source: fine-focus sealed tube	3411 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 10 pixels mm^-1	θmax = 27.4°, θmin = 3.0°
ω scans	h = −8→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −17→17
Tmin = 0.673, Tmax = 0.827	l = −24→24
17967 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: difmap (N-H) and geom (C-H)
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0455P)^2 + 0.877P] where P = (Fo^2 + 2Fc^2)/3
4303 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.37 e Å^−3
1 restraint	Δρmin = −0.21 e Å^−3

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

	x	y	z	Uiso*/Ueq
Fe1	0.71549 (5)	0.65743 (2)	0.556481 (16)	0.04250 (12)
Cl2	0.48747 (10)	0.69533 (5)	0.62004 (3)	0.05641 (18)
Cl1	0.96420 (10)	0.71821 (6)	0.61083 (4)	0.0684 (2)
O3	0.8747 (3)	0.06932 (13)	0.68408 (10)	0.0658 (5)
O1	0.6655 (3)	0.75805 (12)	0.48459 (9)	0.0554 (5)
O2	0.7355 (3)	0.51826 (12)	0.60023 (9)	0.0604 (5)
N1	0.7393 (3)	0.56395 (13)	0.46933 (10)	0.0437 (5)
N2	0.7662 (3)	0.46468 (13)	0.48980 (10)	0.0469 (5)
H19	0.767 (4)	0.4164 (16)	0.4569 (12)	0.070*
C12	0.7858 (3)	0.34449 (16)	0.58836 (12)	0.0433 (5)
C5	0.6525 (3)	0.86496 (16)	0.38373 (12)	0.0399 (5)
C7	0.6114 (4)	0.97428 (19)	0.28109 (14)	0.0578 (7)
H7	0.6031	0.9834	0.2313	0.069*
C3	0.7228 (4)	0.68394 (17)	0.37535 (12)	0.0454 (6)
H3	0.7328	0.6952	0.3265	0.054*
C4	0.6817 (3)	0.76489 (16)	0.41634 (12)	0.0416 (5)
C15	0.8451 (4)	0.15667 (17)	0.64897 (14)	0.0484 (6)
C10	0.6353 (4)	0.94634 (17)	0.42833 (13)	0.0504 (6)
H10	0.6423	0.9376	0.4781	0.061*
C1	0.7958 (4)	0.50882 (18)	0.34653 (13)	0.0539 (7)
H1A	0.9085	0.4798	0.3617	0.081*
H1B	0.8008	0.5393	0.3001	0.081*
H1C	0.7069	0.4579	0.3435	0.081*
C14	0.8337 (4)	0.16853 (17)	0.57535 (14)	0.0502 (6)
H14	0.8462	0.1137	0.5456	0.060*
C2	0.7510 (3)	0.58610 (16)	0.40036 (12)	0.0417 (5)
C11	0.7597 (3)	0.44562 (16)	0.55938 (12)	0.0435 (5)
C17	0.7977 (4)	0.33112 (18)	0.66272 (14)	0.0596 (7)
H17	0.7857	0.3858	0.6926	0.071*
C9	0.6077 (4)	1.04086 (19)	0.39936 (14)	0.0590 (7)
H9	0.5970	1.0952	0.4297	0.071*
C6	0.6391 (4)	0.87999 (18)	0.30961 (13)	0.0527 (6)
H6	0.6488	0.8261	0.2788	0.063*
C8	0.5963 (4)	1.05407 (18)	0.32559 (14)	0.0564 (7)
H8	0.5782	1.1174	0.3061	0.068*
C18	0.8997 (5)	−0.0183 (2)	0.64249 (18)	0.0703 (9)
H18A	0.7947	−0.0313	0.6114	0.105*
H18B	0.9238	−0.0738	0.6743	0.105*
H18C	0.9976	−0.0085	0.6138	0.105*
C16	0.8267 (5)	0.2388 (2)	0.69277 (14)	0.0655 (8)
H16	0.8342	0.2313	0.7427	0.079*
C13	0.8036 (4)	0.26184 (17)	0.54525 (13)	0.0498 (6)
H13	0.7952	0.2691	0.4953	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0665 (2)	0.03262 (17)	0.02835 (16)	0.00726 (15)	0.00375 (14)	0.00282 (12)
Cl2	0.0757 (4)	0.0472 (3)	0.0481 (3)	0.0102 (3)	0.0153 (3)	0.0056 (3)
Cl1	0.0737 (5)	0.0576 (4)	0.0712 (5)	0.0021 (3)	−0.0088 (4)	−0.0033 (3)
O3	0.1039 (16)	0.0398 (9)	0.0545 (11)	0.0118 (10)	0.0116 (10)	0.0170 (8)
O1	0.0961 (14)	0.0385 (8)	0.0326 (8)	0.0149 (9)	0.0109 (9)	0.0074 (7)
O2	0.1114 (16)	0.0350 (8)	0.0356 (9)	0.0157 (9)	0.0110 (9)	0.0042 (7)
N1	0.0656 (13)	0.0310 (9)	0.0340 (10)	0.0046 (9)	0.0017 (9)	0.0029 (7)
N2	0.0787 (15)	0.0289 (9)	0.0331 (10)	0.0067 (9)	0.0052 (10)	0.0029 (7)
C12	0.0579 (14)	0.0351 (11)	0.0369 (11)	0.0050 (10)	0.0043 (10)	0.0056 (9)
C5	0.0493 (13)	0.0360 (11)	0.0345 (11)	0.0030 (10)	0.0041 (10)	0.0068 (9)
C7	0.093 (2)	0.0453 (13)	0.0348 (12)	−0.0001 (14)	0.0023 (13)	0.0111 (10)
C3	0.0675 (16)	0.0380 (11)	0.0308 (11)	0.0049 (11)	0.0050 (11)	0.0066 (9)
C4	0.0518 (14)	0.0397 (11)	0.0329 (11)	0.0025 (10)	0.0021 (10)	0.0058 (9)
C15	0.0606 (15)	0.0384 (12)	0.0466 (13)	0.0059 (11)	0.0058 (11)	0.0131 (10)
C10	0.0748 (18)	0.0423 (12)	0.0350 (12)	0.0092 (12)	0.0091 (12)	0.0058 (10)
C1	0.087 (2)	0.0413 (12)	0.0343 (12)	0.0051 (13)	0.0103 (12)	0.0000 (10)
C14	0.0709 (17)	0.0360 (12)	0.0434 (13)	0.0059 (11)	0.0031 (12)	0.0006 (10)
C2	0.0563 (14)	0.0368 (11)	0.0320 (11)	0.0025 (10)	0.0035 (10)	0.0009 (9)
C11	0.0583 (15)	0.0358 (11)	0.0364 (12)	0.0043 (10)	0.0032 (11)	0.0036 (9)
C17	0.100 (2)	0.0404 (13)	0.0395 (13)	0.0132 (14)	0.0124 (14)	0.0046 (10)
C9	0.093 (2)	0.0380 (12)	0.0470 (14)	0.0123 (13)	0.0140 (14)	0.0019 (11)
C6	0.0843 (19)	0.0380 (12)	0.0353 (12)	0.0013 (12)	0.0031 (12)	0.0030 (9)
C8	0.084 (2)	0.0356 (12)	0.0498 (15)	0.0069 (12)	0.0068 (14)	0.0115 (11)
C18	0.097 (2)	0.0406 (14)	0.074 (2)	0.0133 (15)	0.0125 (18)	0.0121 (13)
C16	0.113 (2)	0.0503 (15)	0.0346 (13)	0.0140 (16)	0.0141 (14)	0.0110 (11)
C13	0.0753 (17)	0.0397 (12)	0.0335 (12)	0.0051 (12)	−0.0003 (11)	0.0045 (9)

Geometric parameters (Å, º)

Fe1—Cl1	2.2192 (8)	C6—H6	0.9300
Fe1—Cl2	2.2382 (7)	C7—C8	1.365 (4)
Fe1—N1	2.070 (2)	C7—C6	1.382 (3)
Fe1—O1	1.916 (2)	C7—H7	0.9300
Fe1—O2	2.039 (2)	C8—H8	0.9300
N1—C2	1.326 (3)	C9—C8	1.378 (4)
O1—C4	1.289 (3)	C9—H9	0.9300
O2—C11	1.259 (3)	C10—C9	1.388 (3)
C3—C4	1.379 (3)	C10—H10	0.9300
N1—N2	1.397 (2)	C12—C13	1.383 (3)
N2—C11	1.324 (3)	C12—C17	1.389 (3)
N2—H19	0.89 (2)	C12—C11	1.468 (3)
O3—C15	1.352 (3)	C14—C13	1.384 (3)
O3—C18	1.430 (3)	C14—H14	0.9300
C1—C2	1.501 (3)	C15—C14	1.373 (3)
C1—H1A	0.9600	C15—C16	1.386 (4)
C1—H1B	0.9600	C17—C16	1.370 (3)
C1—H1C	0.9600	C17—H17	0.9300
C3—C2	1.404 (3)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C5—C10	1.385 (3)	C18—H18C	0.9600
C5—C6	1.387 (3)	C16—H16	0.9300
C5—C4	1.483 (3)	C13—H13	0.9300
Cl1—Fe1—Cl2	110.07 (3)	C7—C6—C5	120.7 (2)
N1—Fe1—Cl1	116.79 (6)	C7—C6—H6	119.7
N1—Fe1—Cl2	132.47 (6)	C7—C8—C9	120.0 (2)
O1—Fe1—Cl1	99.64 (7)	C7—C8—H8	120.0
O1—Fe1—Cl2	95.28 (6)	C8—C7—C6	120.3 (2)
O1—Fe1—N1	84.70 (7)	C8—C7—H7	119.8
O1—Fe1—O2	158.22 (8)	C8—C9—C10	119.9 (2)
O2—Fe1—Cl1	97.16 (6)	C8—C9—H9	120.1
O2—Fe1—Cl2	91.86 (6)	C9—C8—H8	120.0
O2—Fe1—N1	75.37 (7)	C9—C10—H10	119.7
N1—N2—H19	121 (2)	C10—C5—C4	119.3 (2)
N1—C2—C1	121.8 (2)	C10—C5—C6	118.5 (2)
N1—C2—C3	120.6 (2)	C10—C9—H9	120.1
N2—N1—Fe1	112.74 (13)	C11—N2—N1	115.72 (19)
N2—C11—C12	121.5 (2)	C11—N2—H19	122 (2)
O1—C4—C3	122.2 (2)	C11—O2—Fe1	118.66 (15)
O1—C4—C5	116.3 (2)	C12—C13—C14	120.9 (2)
O2—C11—N2	117.3 (2)	C12—C13—H13	119.5
O2—C11—C12	121.2 (2)	C12—C17—H17	119.4
O3—C15—C14	125.1 (2)	C13—C12—C17	118.1 (2)
O3—C15—C16	115.4 (2)	C13—C12—C11	123.2 (2)
O3—C18—H18C	109.5	C13—C14—H14	119.9
O3—C18—H18A	109.5	C14—C13—H13	119.5
O3—C18—H18B	109.5	C14—C15—C16	119.5 (2)
C2—N1—Fe1	129.65 (15)	C15—O3—C18	118.5 (2)
C2—N1—N2	117.19 (19)	C15—C14—C13	120.1 (2)
C2—C1—H1A	109.5	C15—C14—H14	119.9
C2—C1—H1B	109.5	C15—C16—H16	119.9
C2—C1—H1C	109.5	C16—C17—C12	121.1 (2)
C2—C3—H3	116.9	C16—C17—H17	119.4
C3—C2—C1	117.6 (2)	C17—C12—C11	118.7 (2)
C3—C4—C5	121.5 (2)	C17—C16—C15	120.1 (2)
C4—O1—Fe1	134.99 (15)	C17—C16—H16	119.9
C4—C3—C2	126.2 (2)	H1A—C1—H1B	109.5
C4—C3—H3	116.9	H1A—C1—H1C	109.5
C5—C6—H6	119.7	H1B—C1—H1C	109.5
C5—C10—C9	120.6 (2)	H18A—C18—H18B	109.5
C5—C10—H10	119.7	H18A—C18—H18C	109.5
C6—C5—C4	122.2 (2)	H18B—C18—H18C	109.5
C6—C7—H7	119.8
Fe1—N1—N2—C11	4.5 (3)	C2—C3—C4—O1	0.3 (4)
Fe1—O1—C4—C3	10.2 (4)	C2—C3—C4—C5	−179.2 (2)
Fe1—O1—C4—C5	−170.28 (18)	C4—C3—C2—N1	−0.1 (4)
Fe1—N1—C2—C3	−9.1 (4)	C4—C3—C2—C1	−179.5 (3)
Fe1—N1—C2—C1	170.31 (19)	C4—C5—C6—C7	179.9 (3)
Fe1—O2—C11—N2	−1.6 (3)	C4—C5—C10—C9	−180.0 (3)
Fe1—O2—C11—C12	176.29 (18)	C5—C10—C9—C8	0.4 (5)
Cl1—Fe1—N1—N2	86.83 (17)	C6—C5—C4—O1	−169.9 (2)
Cl1—Fe1—N1—C2	−85.4 (2)	C6—C5—C10—C9	−0.9 (4)
Cl1—Fe1—O1—C4	102.7 (2)	C6—C5—C4—C3	9.6 (4)
Cl1—Fe1—O2—C11	−112.7 (2)	C6—C7—C8—C9	−0.3 (5)
Cl2—Fe1—N1—N2	−82.72 (17)	C8—C7—C6—C5	−0.2 (5)
Cl2—Fe1—N1—C2	105.1 (2)	C10—C5—C4—O1	9.1 (3)
Cl2—Fe1—O1—C4	−145.9 (2)	C10—C5—C4—C3	−171.3 (2)
Cl2—Fe1—O2—C11	136.8 (2)	C10—C5—C6—C7	0.8 (4)
N1—Fe1—O1—C4	−13.6 (3)	C10—C9—C8—C7	0.2 (5)
N1—Fe1—O2—C11	3.1 (2)	C11—C12—C13—C14	177.9 (3)
N1—N2—C11—O2	−2.0 (4)	C11—C12—C17—C16	−178.2 (3)
N1—N2—C11—C12	−179.9 (2)	C12—C17—C16—C15	0.1 (5)
N2—N1—C2—C3	179.0 (2)	C13—C12—C11—N2	−5.7 (4)
N2—N1—C2—C1	−1.6 (4)	C13—C12—C11—O2	176.5 (3)
O1—Fe1—N1—N2	−175.03 (18)	C13—C12—C17—C16	0.2 (5)
O1—Fe1—N1—C2	12.8 (2)	C14—C15—C16—C17	−0.1 (5)
O1—Fe1—O2—C11	27.5 (4)	C15—C14—C13—C12	0.5 (4)
O2—Fe1—N1—N2	−3.89 (16)	C16—C15—C14—C13	−0.2 (4)
O2—Fe1—N1—C2	−176.1 (2)	C17—C12—C11—N2	172.7 (3)
O2—Fe1—O1—C4	−37.3 (4)	C17—C12—C11—O2	−5.1 (4)
O3—C15—C14—C13	−179.7 (3)	C17—C12—C13—C14	−0.5 (4)
O3—C15—C16—C17	179.5 (3)	C18—O3—C15—C14	1.2 (4)
C2—N1—N2—C11	177.8 (2)	C18—O3—C15—C16	−178.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H19···Cl2^i	0.89 (2)	2.75 (2)	3.438 (2)	135 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.