Dichloro­(methanol-κO)[2-(2-pyridylmethyl­imino­meth­yl)phenolato-κ³N,N′,O]iron(III)

In the crystal structure of the methanol-coordinated mononuclear title compound, [Fe(C₁₃H₁₁N₂O)Cl₂(CH₄O)], the Fe^III atom is six-coordinate in an octa­hedral environment and the Cl atoms are cis to each other. Hydrogen bonds between the hydroxyl group of the methanol ligand and the Cl atom of an adjacent mol­ecule lead to the formation of a chain that runs along the b axis of the ortho­rhom­bic unit cell.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.025
• wR factor = 0.062
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.486     0.881
            Tmin(prime) and Tmax expected:      0.709     0.878
            RR(prime) =      0.683
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.68

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C7      ..       6.26 su
PLAT731_ALERT_1_C Bond    Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Rat
              O2   -H2O     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Rat
              O2   -H2O     1.555   1.555
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.01

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               3571
           Count of symmetry unique reflns         1894
           Completeness (_total/calc)            188.54%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1677
           Fraction of Friedel pairs measured     0.885
           Are heavy atom types Z>Si present        yes

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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)[2-(2-pyridylmethyliminomethyl)phenolato- κ³N,N',O]iron(III)

Crystal data

[Fe(C13H11N2O)Cl2(CH4O)]	F(000) = 756
Mr = 370.03	Dx = 1.566 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3270 reflections
a = 19.428 (1) Å	θ = 2.5–25.6°
b = 7.0016 (5) Å	µ = 1.31 mm^−1
c = 11.5352 (8) Å	T = 295 K
V = 1569.13 (19) Å^3	Block, purple
Z = 4	0.26 × 0.14 × 0.10 mm

Data collection

Bruker APEX-II area-detector diffractometer	3571 independent reflections
Radiation source: fine-focus sealed tube	3144 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −25→25
Tmin = 0.486, Tmax = 0.881	k = −6→9
9057 measured reflections	l = −14→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.062	w = 1/[σ^2(Fo^2) + (0.0292P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max = 0.001
3571 reflections	Δρmax = 0.21 e Å^−3
195 parameters	Δρmin = −0.20 e Å^−3
2 restraints	Absolute structure: Flack (1983), with 1679 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (1)

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

	x	y	z	Uiso*/Ueq
Fe1	0.44562 (1)	0.84686 (4)	0.50000 (3)	0.03036 (8)
Cl1	0.38263 (3)	1.00791 (8)	0.36332 (5)	0.0409 (1)
Cl2	0.41597 (3)	0.53594 (7)	0.44195 (6)	0.0460 (2)
O1	0.5327 (1)	0.8572 (2)	0.4274 (2)	0.0459 (4)
O2	0.4602 (1)	1.1357 (2)	0.5723 (2)	0.0502 (5)
N1	0.4966 (1)	0.7517 (3)	0.6504 (2)	0.0324 (4)
N2	0.3636 (1)	0.8275 (3)	0.6263 (2)	0.0352 (4)
C1	0.5956 (1)	0.7920 (3)	0.4554 (2)	0.0383 (5)
C2	0.6474 (1)	0.8032 (3)	0.3728 (3)	0.0496 (6)
C3	0.7141 (1)	0.7437 (4)	0.4010 (3)	0.0597 (9)
C4	0.7288 (1)	0.6713 (4)	0.5093 (4)	0.0641 (8)
C5	0.6779 (1)	0.6550 (3)	0.5898 (3)	0.0549 (7)
C6	0.6098 (1)	0.7169 (3)	0.5656 (2)	0.0373 (5)
C7	0.5600 (1)	0.7016 (3)	0.6567 (2)	0.0365 (5)
C8	0.4548 (1)	0.7303 (4)	0.7556 (2)	0.0455 (6)
C9	0.3796 (1)	0.7534 (3)	0.7298 (2)	0.0360 (5)
C10	0.3300 (1)	0.7039 (3)	0.8102 (3)	0.0492 (6)
C11	0.2616 (1)	0.7375 (4)	0.7837 (3)	0.0551 (8)
C12	0.2451 (1)	0.8197 (4)	0.6791 (3)	0.0556 (7)
C13	0.2967 (1)	0.8611 (3)	0.6030 (2)	0.0457 (6)
C14	0.5206 (2)	1.2127 (4)	0.6220 (3)	0.073 (1)
H2O	0.441 (2)	1.215 (4)	0.529 (3)	0.09 (1)*
H2	0.6379	0.8501	0.2991	0.060*
H3	0.7489	0.7532	0.3460	0.072*
H4	0.7734	0.6337	0.5273	0.077*
H5	0.6879	0.6025	0.6619	0.066*
H7	0.5750	0.6509	0.7268	0.044*
H8A	0.4687	0.8253	0.8122	0.055*
H8B	0.4628	0.6051	0.7890	0.055*
H10	0.3423	0.6492	0.8807	0.059*
H11	0.2272	0.7048	0.8361	0.066*
H12	0.1996	0.8466	0.6605	0.067*
H13	0.2852	0.9149	0.5318	0.055*
H14A	0.5097	1.2703	0.6952	0.110*
H14B	0.5395	1.3075	0.5710	0.110*
H14C	0.5537	1.1126	0.6335	0.110*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0286 (1)	0.0328 (1)	0.0297 (1)	0.0013 (1)	0.0007 (2)	0.0022 (1)
Cl1	0.0365 (3)	0.0468 (3)	0.0394 (3)	0.0015 (2)	−0.0056 (2)	0.0086 (2)
Cl2	0.0589 (4)	0.0345 (3)	0.0447 (3)	0.0023 (3)	−0.0020 (3)	−0.0079 (3)
O1	0.033 (1)	0.058 (1)	0.046 (1)	0.008 (1)	0.006 (1)	0.014 (1)
O2	0.056 (1)	0.033 (1)	0.062 (1)	−0.001 (1)	−0.020 (1)	0.001 (1)
N1	0.035 (1)	0.032 (1)	0.031 (1)	0.001 (1)	−0.004 (1)	0.001 (1)
N2	0.037 (1)	0.034 (1)	0.035 (1)	0.002 (1)	0.005 (1)	−0.003 (1)
C1	0.030 (1)	0.030 (1)	0.055 (2)	−0.001 (1)	0.003 (1)	0.001 (1)
C2	0.042 (1)	0.038 (1)	0.069 (2)	−0.001 (1)	0.016 (1)	0.005 (1)
C3	0.035 (1)	0.044 (1)	0.101 (3)	−0.005 (1)	0.019 (1)	−0.012 (2)
C4	0.030 (1)	0.060 (2)	0.102 (3)	0.005 (1)	−0.006 (2)	−0.019 (2)
C5	0.041 (1)	0.050 (2)	0.074 (2)	0.006 (1)	−0.014 (1)	−0.011 (1)
C6	0.030 (1)	0.031 (1)	0.051 (2)	0.002 (1)	−0.005 (1)	−0.006 (1)
C7	0.044 (1)	0.030 (1)	0.036 (1)	−0.001 (1)	−0.009 (1)	−0.002 (1)
C8	0.049 (1)	0.056 (2)	0.032 (1)	0.001 (1)	0.001 (1)	0.003 (1)
C9	0.043 (1)	0.029 (1)	0.036 (1)	0.002 (1)	0.007 (1)	−0.002 (1)
C10	0.062 (2)	0.043 (1)	0.042 (1)	−0.004 (1)	0.019 (1)	−0.002 (1)
C11	0.052 (2)	0.051 (1)	0.063 (2)	−0.007 (1)	0.025 (1)	−0.004 (1)
C12	0.037 (1)	0.065 (2)	0.064 (2)	0.005 (1)	0.012 (1)	−0.006 (2)
C13	0.038 (1)	0.052 (1)	0.048 (2)	0.008 (1)	0.005 (1)	−0.002 (1)
C14	0.086 (2)	0.044 (2)	0.090 (3)	−0.010 (1)	−0.043 (2)	−0.004 (2)

Geometric parameters (Å, º)

Fe1—Cl1	2.292 (1)	C9—C10	1.383 (3)
Fe1—Cl2	2.349 (1)	C10—C11	1.383 (4)
Fe1—O1	1.889 (2)	C11—C12	1.375 (4)
Fe1—O2	2.206 (2)	C12—C13	1.364 (4)
Fe1—N1	2.106 (2)	O2—H2O	0.84 (1)
Fe1—N2	2.163 (2)	C2—H2	0.93
O1—C1	1.343 (3)	C3—H3	0.93
O2—C14	1.413 (3)	C4—H4	0.93
N1—C7	1.283 (3)	C5—H5	0.93
N1—C8	1.468 (3)	C7—H7	0.93
N2—C9	1.338 (3)	C8—H8A	0.97
N2—C13	1.348 (3)	C8—H8B	0.97
C1—C2	1.389 (3)	C10—H10	0.93
C1—C6	1.403 (3)	C11—H11	0.93
C2—C3	1.398 (4)	C12—H12	0.93
C3—C4	1.378 (6)	C13—H13	0.93
C4—C5	1.361 (5)	C14—H14A	0.96
C5—C6	1.420 (3)	C14—H14B	0.96
C6—C7	1.433 (3)	C14—H14C	0.96
C8—C9	1.499 (3)
Cl1—Fe1—Cl2	97.41 (3)	C10—C9—C8	121.3 (2)
Cl1—Fe1—O1	98.88 (5)	C9—C10—C11	118.6 (3)
Cl1—Fe1—O2	82.99 (5)	C12—C11—C10	119.3 (2)
Cl1—Fe1—N1	166.74 (5)	C13—C12—C11	118.9 (3)
Cl1—Fe1—N2	95.79 (5)	N2—C13—C12	122.9 (3)
Cl2—Fe1—O1	97.40 (6)	Fe1—O2—H2O	109 (3)
Cl2—Fe1—O2	171.42 (6)	C14—O2—H2O	112 (2)
Cl2—Fe1—N1	93.26 (5)	C1—C2—H2	120.2
Cl2—Fe1—N2	87.33 (5)	C3—C2—H2	120.2
O1—Fe1—O2	91.00 (8)	C4—C3—H3	119.6
O1—Fe1—N1	87.49 (7)	C2—C3—H3	119.6
O1—Fe1—N2	163.85 (8)	C5—C4—H4	120.0
O2—Fe1—N1	85.30 (7)	C3—C4—H4	120.0
O2—Fe1—N2	84.10 (7)	C4—C5—H5	119.5
N1—Fe1—N2	76.80 (7)	C6—C5—H5	119.5
C1—O1—Fe1	134.0 (2)	N1—C7—H7	117.0
C14—O2—Fe1	127.6 (2)	C6—C7—H7	117.0
C7—N1—C8	117.1 (2)	N1—C8—H8A	109.4
C7—N1—Fe1	125.8 (2)	C9—C8—H8A	109.4
C8—N1—Fe1	117.0 (1)	N1—C8—H8B	109.4
C9—N2—C13	118.0 (2)	C9—C8—H8B	109.4
C9—N2—Fe1	117.0 (2)	H8A—C8—H8B	108.0
C13—N2—Fe1	124.4 (2)	C9—C10—H10	120.7
O1—C1—C2	118.4 (2)	C11—C10—H10	120.7
O1—C1—C6	121.7 (2)	C12—C11—H11	120.4
C2—C1—C6	120.0 (2)	C10—C11—H11	120.4
C1—C2—C3	119.7 (3)	C13—C12—H12	120.6
C4—C3—C2	120.8 (3)	C11—C12—H12	120.6
C5—C4—C3	119.9 (2)	N2—C13—H13	118.5
C4—C5—C6	121.1 (3)	C12—C13—H13	118.5
C1—C6—C5	118.5 (2)	O2—C14—H14A	109.5
C1—C6—C7	124.00 (19)	O2—C14—H14B	109.5
C5—C6—C7	117.5 (2)	H14A—C14—H14B	109.5
N1—C7—C6	125.9 (2)	O2—C14—H14C	109.5
N1—C8—C9	111.3 (2)	H14A—C14—H14C	109.5
N2—C9—C10	122.3 (2)	H14B—C14—H14C	109.5
N2—C9—C8	116.4 (2)
N1—Fe1—O1—C1	12.1 (2)	O1—C1—C2—C3	177.4 (2)
N2—Fe1—O1—C1	25.3 (4)	C6—C1—C2—C3	−1.5 (3)
O2—Fe1—O1—C1	97.3 (2)	C1—C2—C3—C4	1.0 (4)
Cl1—Fe1—O1—C1	−179.6 (2)	C2—C3—C4—C5	0.8 (4)
Cl2—Fe1—O1—C1	−80.9 (2)	C3—C4—C5—C6	−1.9 (4)
O1—Fe1—O2—C14	−41.9 (3)	O1—C1—C6—C5	−178.5 (2)
N1—Fe1—O2—C14	45.5 (3)	C2—C1—C6—C5	0.4 (3)
N2—Fe1—O2—C14	122.7 (3)	O1—C1—C6—C7	0.3 (3)
Cl1—Fe1—O2—C14	−140.7 (3)	C2—C1—C6—C7	179.2 (2)
O1—Fe1—N1—C7	−9.7 (2)	C4—C5—C6—C1	1.3 (3)
N2—Fe1—N1—C7	174.0 (2)	C4—C5—C6—C7	−177.6 (2)
O2—Fe1—N1—C7	−100.9 (2)	C8—N1—C7—C6	−177.8 (2)
Cl1—Fe1—N1—C7	−128.9 (2)	Fe1—N1—C7—C6	5.9 (3)
Cl2—Fe1—N1—C7	87.6 (2)	C1—C6—C7—N1	0.7 (3)
O1—Fe1—N1—C8	174.0 (2)	C5—C6—C7—N1	179.5 (2)
N2—Fe1—N1—C8	−2.2 (2)	C7—N1—C8—C9	−167.8 (2)
O2—Fe1—N1—C8	82.8 (2)	Fe1—N1—C8—C9	8.8 (3)
Cl1—Fe1—N1—C8	54.8 (3)	C13—N2—C9—C10	2.6 (3)
Cl2—Fe1—N1—C8	−88.7 (2)	Fe1—N2—C9—C10	−168.9 (2)
O1—Fe1—N2—C9	−19.4 (3)	C13—N2—C9—C8	−176.0 (2)
N1—Fe1—N2—C9	−5.7 (2)	Fe1—N2—C9—C8	12.5 (3)
O2—Fe1—N2—C9	−92.3 (2)	N1—C8—C9—N2	−13.7 (3)
Cl1—Fe1—N2—C9	−174.6 (2)	N1—C8—C9—C10	167.6 (2)
Cl2—Fe1—N2—C9	88.3 (2)	N2—C9—C10—C11	−1.9 (3)
O1—Fe1—N2—C13	169.7 (2)	C8—C9—C10—C11	176.8 (2)
N1—Fe1—N2—C13	−176.6 (2)	C9—C10—C11—C12	−0.4 (4)
O2—Fe1—N2—C13	96.8 (2)	C10—C11—C12—C13	1.8 (4)
Cl1—Fe1—N2—C13	14.5 (2)	C9—N2—C13—C12	−1.2 (4)
Cl2—Fe1—N2—C13	−82.7 (2)	Fe1—N2—C13—C12	169.6 (2)
Fe1—O1—C1—C2	171.4 (2)	C11—C12—C13—N2	−1.0 (4)
Fe1—O1—C1—C6	−9.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···Cl2^i	0.84 (1)	2.51 (2)	3.295 (2)	157 (3)

Symmetry code: (i) x, y+1, z.