Di­chloro­(methanol-κO)[3-methoxy­salicyl­aldehyde (4-methoxy­benzoyl)­hydrazonato-κ³O,O′,N]­iron(III) methanol solvate

The Fe^III atom in the title complex, [Fe(HL)Cl₂(CH₃OH)]·CH₃OH, [H₂L = 3-methoxy­salicyl­aldehyde (4-methoxy­benzoyl)­hydrazone, C₁₆H₁₅N₂O₄], is coordinated by two O atoms and one N atom of the tridentate hydrazone ligand, two chloride anions and one methanol mol­ecule, thus defining a distorted octahedral geometry. A chain structure is constructed by hydrogen-bond interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.065
• wR factor = 0.187
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H20    ..  H21     ..       2.02 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C H4 O

   0 ALERT level A = In general: serious problem
   1 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 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.

Dichloro(methanol-κO)[3-methoxysalicylaldehyde (4-methoxybenzoyl)hydrazonato-κ³O,O',N]iron(III) methanol solvate

Crystal data

[Fe(C16H15N2O4)Cl2(CH4O)]·CH4O	F(000) = 1012
Mr = 490.13	Dx = 1.526 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12723 reflections
a = 17.226 (3) Å	θ = 3.0–27.4°
b = 10.622 (2) Å	µ = 0.99 mm^−1
c = 12.096 (2) Å	T = 293 K
β = 105.42 (3)°	Prism, black
V = 2133.6 (7) Å^3	0.37 × 0.23 × 0.16 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	4757 independent reflections
Radiation source: fine-focus sealed tube	2849 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −22→22
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
Tmin = 0.710, Tmax = 0.857	l = −15→15
12872 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.187	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0998P)^2] where P = (Fo^2 + 2Fc^2)/3
4757 reflections	(Δ/σ)max = 0.001
272 parameters	Δρmax = 0.64 e Å^−3
3 restraints	Δρmin = −0.38 e Å^−3

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

	x	y	z	Uiso*/Ueq
Fe1	0.74674 (4)	0.19978 (6)	0.03200 (5)	0.0353 (2)
Cl1	0.66140 (8)	0.2019 (1)	−0.14449 (9)	0.0484 (3)
Cl2	0.82587 (9)	0.0399 (1)	−0.0013 (1)	0.0569 (4)
N1	0.8045 (2)	0.1964 (3)	0.2116 (3)	0.0318 (8)
N2	0.7746 (2)	0.1027 (4)	0.2665 (3)	0.0337 (8)
O1	0.8168 (2)	0.3366 (3)	0.0284 (2)	0.0385 (8)
O2	0.6852 (2)	0.0710 (3)	0.0999 (2)	0.0403 (8)
O3	0.8806 (2)	0.5276 (3)	−0.0447 (3)	0.0507 (9)
O4	0.5642 (2)	−0.3237 (4)	0.4002 (3)	0.060 (1)
O5	0.6747 (2)	0.3394 (3)	0.0784 (3)	0.0440 (8)
O6	0.7247 (3)	−0.0239 (4)	−0.2728 (3)	0.067 (1)
C1	0.8706 (3)	0.3970 (4)	0.1052 (4)	0.035 (1)
C2	0.9072 (3)	0.5029 (5)	0.0695 (4)	0.040 (1)
C3	0.9633 (3)	0.5714 (6)	0.1460 (5)	0.057 (2)
C4	0.9881 (3)	0.5378 (6)	0.2600 (5)	0.058 (2)
C5	0.9543 (3)	0.4356 (5)	0.2970 (4)	0.049 (1)
C6	0.8962 (3)	0.3649 (4)	0.2229 (4)	0.037 (1)
C7	0.8595 (3)	0.2657 (4)	0.2702 (4)	0.033 (1)
C8	0.9021 (4)	0.6450 (6)	−0.0862 (5)	0.062 (2)
C9	0.7110 (3)	0.0444 (4)	0.2041 (3)	0.033 (1)
C10	0.6744 (3)	−0.0524 (4)	0.2566 (4)	0.032 (1)
C11	0.6840 (3)	−0.0590 (5)	0.3744 (4)	0.044 (1)
C12	0.6455 (3)	−0.1493 (5)	0.4170 (4)	0.053 (1)
C13	0.5987 (3)	−0.2382 (5)	0.3477 (4)	0.042 (1)
C14	0.5876 (3)	−0.2316 (5)	0.2308 (4)	0.040 (1)
C15	0.6239 (3)	−0.1386 (4)	0.1853 (4)	0.036 (1)
C16	0.5211 (4)	−0.4244 (6)	0.3362 (6)	0.070 (2)
C17	0.5928 (3)	0.3411 (6)	0.0542 (5)	0.063 (2)
C18	0.7738 (4)	−0.1279 (6)	−0.2682 (6)	0.066 (2)
H3	0.9853	0.6424	0.1210	0.068*
H4	1.0275	0.5844	0.3112	0.070*
H5	0.9709	0.4131	0.3740	0.059*
H7	0.8772	0.2513	0.3487	0.039*
H8A	0.8796	0.6496	−0.1677	0.094*
H8B	0.9597	0.6514	−0.0688	0.094*
H8C	0.8815	0.7129	−0.0500	0.094*
H11	0.7169	−0.0016	0.4233	0.053*
H12	0.6506	−0.1515	0.4955	0.063*
H14	0.5554	−0.2906	0.1830	0.048*
H15	0.6149	−0.1326	0.1062	0.043*
H16A	0.5004	−0.4778	0.3858	0.105*
H16B	0.5563	−0.4722	0.3026	0.105*
H16C	0.4772	−0.3918	0.2765	0.105*
H17A	0.5758	0.4159	0.0859	0.095*
H17B	0.5746	0.2683	0.0872	0.095*
H17C	0.5702	0.3404	−0.0274	0.095*
H18A	0.8274	−0.1081	−0.2237	0.099*
H18B	0.7748	−0.1511	−0.3445	0.099*
H18C	0.7532	−0.1968	−0.2331	0.099*
H19	0.798 (3)	0.091 (5)	0.342 (1)	0.051*
H20	0.696 (3)	0.405 (3)	0.112 (4)	0.066*
H21	0.726 (5)	0.034 (5)	−0.224 (5)	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0367 (4)	0.0445 (4)	0.0222 (3)	−0.0085 (3)	0.0036 (3)	0.0024 (3)
Cl1	0.0499 (8)	0.0637 (9)	0.0255 (5)	−0.0080 (6)	−0.0005 (5)	0.0028 (5)
Cl2	0.0620 (9)	0.0632 (9)	0.0429 (7)	0.0120 (7)	0.0093 (6)	−0.0053 (6)
N1	0.038 (2)	0.034 (2)	0.024 (2)	−0.001 (2)	0.010 (2)	0.000 (2)
N2	0.033 (2)	0.042 (2)	0.024 (2)	−0.001 (2)	0.004 (2)	0.004 (2)
O1	0.043 (2)	0.044 (2)	0.025 (1)	−0.010 (1)	0.004 (1)	0.003 (1)
O2	0.042 (2)	0.051 (2)	0.024 (1)	−0.012 (2)	0.003 (1)	0.004 (1)
O3	0.053 (2)	0.059 (2)	0.037 (2)	−0.017 (2)	0.006 (2)	0.010 (2)
O4	0.069 (3)	0.061 (3)	0.048 (2)	−0.030 (2)	0.011 (2)	0.012 (2)
O5	0.036 (2)	0.054 (2)	0.040 (2)	−0.002 (2)	0.006 (2)	−0.003 (2)
O6	0.082 (3)	0.056 (3)	0.058 (2)	0.013 (2)	0.010 (2)	0.002 (2)
C1	0.031 (2)	0.041 (3)	0.032 (2)	−0.001 (2)	0.007 (2)	−0.001 (2)
C2	0.031 (3)	0.047 (3)	0.039 (2)	−0.005 (2)	0.005 (2)	0.005 (2)
C3	0.051 (3)	0.061 (4)	0.053 (3)	−0.019 (3)	0.005 (3)	0.008 (3)
C4	0.042 (3)	0.068 (4)	0.056 (3)	−0.021 (3)	−0.003 (3)	−0.011 (3)
C5	0.045 (3)	0.059 (3)	0.039 (3)	−0.011 (2)	0.005 (2)	0.000 (2)
C6	0.036 (3)	0.036 (2)	0.036 (2)	−0.002 (2)	0.007 (2)	−0.003 (2)
C7	0.029 (2)	0.041 (3)	0.026 (2)	0.007 (2)	0.003 (2)	0.002 (2)
C8	0.066 (4)	0.058 (4)	0.061 (4)	−0.007 (3)	0.014 (3)	0.017 (3)
C9	0.040 (3)	0.031 (2)	0.028 (2)	0.001 (2)	0.010 (2)	0.000 (2)
C10	0.033 (2)	0.033 (2)	0.028 (2)	0.004 (2)	0.008 (2)	0.002 (2)
C11	0.054 (3)	0.051 (3)	0.027 (2)	−0.016 (2)	0.010 (2)	−0.008 (2)
C12	0.064 (4)	0.066 (4)	0.027 (2)	−0.022 (3)	0.010 (2)	0.004 (2)
C13	0.037 (3)	0.046 (3)	0.043 (3)	−0.001 (2)	0.009 (2)	0.007 (2)
C14	0.040 (3)	0.039 (3)	0.035 (2)	−0.004 (2)	0.000 (2)	−0.004 (2)
C15	0.033 (3)	0.043 (3)	0.027 (2)	0.002 (2)	0.002 (2)	−0.003 (2)
C16	0.066 (4)	0.060 (4)	0.079 (4)	−0.029 (3)	0.008 (4)	0.009 (3)
C17	0.039 (3)	0.102 (5)	0.050 (3)	0.008 (3)	0.012 (3)	0.001 (3)
C18	0.047 (4)	0.055 (4)	0.086 (4)	−0.001 (3)	0.002 (3)	−0.003 (3)

Geometric parameters (Å, º)

Fe1—Cl1	2.247 (2)	C5—C6	1.375 (7)
Fe1—Cl2	2.280 (2)	C5—H5	0.9300
Fe1—N1	2.135 (4)	C6—C7	1.425 (6)
Fe1—O1	1.897 (3)	C7—H7	0.9300
Fe1—O2	2.033 (3)	C8—H8A	0.9600
Fe1—O5	2.104 (4)	C8—H8B	0.9600
N1—N2	1.371 (5)	C8—H8C	0.9600
N1—C7	1.259 (6)	C9—C10	1.439 (6)
N2—C9	1.309 (6)	C10—C11	1.392 (6)
O1—C1	1.294 (5)	C10—C15	1.393 (6)
O2—C9	1.253 (5)	C11—C12	1.345 (7)
N2—H19	0.903 (17)	C11—H11	0.9300
O3—C2	1.360 (5)	C12—C13	1.373 (7)
O3—C8	1.430 (6)	C12—H12	0.9300
O4—C13	1.335 (6)	C13—C14	1.377 (7)
O4—C16	1.411 (6)	C14—C15	1.361 (7)
O5—C17	1.362 (6)	C14—H14	0.9300
O5—H20	0.84 (4)	C15—H15	0.9300
O6—C18	1.383 (7)	C16—H16A	0.9600
O6—H21	0.85 (6)	C16—H16B	0.9600
C1—C2	1.412 (6)	C16—H16C	0.9600
C1—C6	1.415 (6)	C17—H17A	0.9600
C2—C3	1.358 (7)	C17—H17B	0.9600
C3—C4	1.378 (7)	C17—H17C	0.9600
C3—H3	0.9300	C18—H18A	0.9600
C4—C5	1.362 (7)	C18—H18B	0.9600
C4—H4	0.9300	C18—H18C	0.9600
Cl1—Fe1—Cl2	96.34 (6)	C3—C4—H4	120.4
N1—Fe1—Cl1	167.6 (1)	C4—C3—H3	119.4
N1—Fe1—Cl2	91.6 (1)	C4—C5—C6	121.4 (5)
O1—Fe1—Cl1	103.3 (1)	C4—C5—H5	119.3
O1—Fe1—Cl2	98.8 (1)	C5—C4—C3	119.3 (5)
O1—Fe1—N1	84.8 (1)	C5—C4—H4	120.4
O1—Fe1—O2	158.2 (1)	C5—C6—C1	120.1 (4)
O1—Fe1—O5	83.7 (1)	C5—C6—C7	117.8 (4)
O2—Fe1—Cl1	96.35 (9)	C6—C5—H5	119.3
O2—Fe1—Cl2	88.3 (1)	C6—C7—H7	118.2
O2—Fe1—N1	74.3 (1)	C7—N1—Fe1	129.8 (3)
O2—Fe1—O5	87.6 (1)	C7—N1—N2	118.3 (4)
O5—Fe1—Cl1	87.9 (1)	C9—N2—N1	115.4 (3)
O5—Fe1—Cl2	174.4 (1)	C9—N2—H19	127 (3)
O5—Fe1—N1	83.6 (1)	C9—O2—Fe1	118.3 (3)
Fe1—O5—H20	120 (4)	C10—C11—H11	120.3
N1—N2—H19	118 (3)	C10—C15—H15	119.8
N1—C7—C6	123.6 (4)	C11—C10—C9	122.7 (4)
N1—C7—H7	118.2	C11—C10—C15	119.0 (4)
N2—N1—Fe1	111.8 (3)	C11—C12—C13	121.7 (4)
N2—C9—C10	118.8 (4)	C11—C12—H12	119.2
O1—C1—C2	117.9 (4)	C12—C11—C10	119.5 (5)
O1—C1—C6	125.1 (4)	C12—C11—H11	120.3
O2—C9—N2	119.5 (4)	C12—C13—C14	119.4 (5)
O2—C9—C10	121.6 (4)	C13—O4—C16	119.4 (4)
O3—C2—C1	114.0 (4)	C13—C12—H12	119.2
O3—C8—H8A	109.5	C13—C14—H14	120.0
O3—C8—H8B	109.5	C14—C15—C10	120.4 (4)
O3—C8—H8C	109.5	C14—C15—H15	119.8
O4—C13—C12	116.2 (4)	C15—C10—C9	118.2 (4)
O4—C13—C14	124.4 (5)	C15—C14—C13	119.9 (5)
O4—C16—H16A	109.5	C15—C14—H14	120.0
O4—C16—H16B	109.5	C17—O5—Fe1	127.1 (4)
O4—C16—H16C	109.5	C17—O5—H20	113 (4)
O5—C17—H17A	109.5	C18—O6—H21	130 (5)
O5—C17—H17B	109.5	H8A—C8—H8B	109.5
O5—C17—H17C	109.5	H8A—C8—H8C	109.5
O6—C18—H18A	109.5	H8B—C8—H8C	109.5
O6—C18—H18B	109.5	H16A—C16—H16B	109.5
O6—C18—H18C	109.5	H16A—C16—H16C	109.5
C1—O1—Fe1	134.5 (3)	H16B—C16—H16C	109.5
C1—C6—C7	122.0 (4)	H17A—C17—H17B	109.5
C2—O3—C8	118.4 (4)	H17A—C17—H17C	109.5
C2—C1—C6	117.0 (4)	H17B—C17—H17C	109.5
C2—C3—C4	121.3 (5)	H18A—C18—H18B	109.5
C2—C3—H3	119.4	H18A—C18—H18C	109.5
C3—C2—O3	125.1 (4)	H18B—C18—H18C	109.5
C3—C2—C1	120.9 (4)
Fe1—N1—N2—C9	−8.3 (5)	O2—C9—C10—C11	−159.8 (5)
Fe1—N1—C7—C6	−0.9 (7)	O2—C9—C10—C15	16.8 (7)
Fe1—O1—C1—C2	−175.1 (3)	O3—C2—C3—C4	−178.4 (5)
Fe1—O1—C1—C6	5.2 (7)	O4—C13—C14—C15	178.3 (5)
Fe1—O2—C9—N2	2.2 (6)	O5—Fe1—N1—C7	−83.8 (4)
Fe1—O2—C9—C10	−175.4 (3)	O5—Fe1—N1—N2	96.2 (3)
Cl1—Fe1—N1—N2	49.1 (7)	O5—Fe1—O1—C1	81.6 (4)
Cl1—Fe1—N1—C7	−130.9 (5)	O5—Fe1—O2—C9	−89.2 (3)
Cl1—Fe1—O1—C1	167.9 (4)	C1—C2—C3—C4	2.1 (9)
Cl1—Fe1—O2—C9	−176.8 (3)	C1—C6—C7—N1	2.9 (7)
Cl2—Fe1—N1—N2	−80.9 (3)	C2—C1—C6—C5	0.0 (7)
Cl2—Fe1—N1—C7	99.1 (4)	C2—C1—C6—C7	175.4 (4)
Cl2—Fe1—O1—C1	−93.4 (4)	C2—C3—C4—C5	−1.6 (9)
Cl2—Fe1—O2—C9	87.0 (3)	C3—C4—C5—C6	0.3 (9)
N1—Fe1—O1—C1	−2.5 (4)	C4—C5—C6—C1	0.5 (8)
N1—Fe1—O2—C9	−5.1 (3)	C4—C5—C6—C7	−175.1 (5)
N1—Fe1—O5—C17	−125.6 (4)	C5—C6—C7—N1	178.4 (5)
N1—N2—C9—O2	4.4 (6)	C6—C1—C2—O3	179.2 (4)
N1—N2—C9—C10	−177.9 (4)	C6—C1—C2—C3	−1.2 (7)
N2—N1—C7—C6	179.1 (4)	C7—N1—N2—C9	171.7 (4)
N2—C9—C10—C11	22.6 (7)	C8—O3—C2—C3	−11.1 (8)
N2—C9—C10—C15	−160.8 (4)	C8—O3—C2—C1	168.5 (4)
O1—Fe1—N1—C7	0.4 (4)	C9—C10—C11—C12	177.4 (5)
O1—Fe1—N1—N2	−179.6 (3)	C9—C10—C15—C14	−179.8 (4)
O1—Fe1—O2—C9	−22.7 (6)	C10—C11—C12—C13	2.3 (9)
O1—Fe1—O5—C17	149.0 (4)	C11—C12—C13—O4	179.2 (5)
O1—C1—C2—O3	−0.5 (6)	C11—C12—C13—C14	−3.3 (9)
O1—C1—C2—C3	179.1 (5)	C11—C10—C15—C14	−3.1 (7)
O1—C1—C6—C5	179.6 (5)	C12—C13—C14—C15	1.0 (8)
O1—C1—C6—C7	−4.9 (7)	C13—C14—C15—C10	2.1 (7)
O2—Fe1—N1—C7	−173.1 (4)	C15—C10—C11—C12	0.9 (8)
O2—Fe1—N1—N2	6.9 (3)	C16—O4—C13—C12	−174.5 (5)
O2—Fe1—O1—C1	14.4 (7)	C16—O4—C13—C14	8.1 (8)
O2—Fe1—O5—C17	−51.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H19···O1^i	0.90 (2)	2.33 (3)	3.123 (4)	148 (4)
N2—H19···O3^i	0.90 (2)	2.11 (3)	2.872 (5)	142 (4)
O5—H20···O6^i	0.84 (4)	1.84 (2)	2.646 (5)	158 (6)
O6—H21···Cl1	0.85 (6)	2.43 (4)	3.201 (4)	151 (7)
O6—H21···Cl2	0.85 (6)	2.79 (6)	3.352 (5)	126 (6)

Symmetry code: (i) x, −y+1/2, z+1/2.