The title compound (systematic name: aqua{2,2′-[propane-1,3-diylbis(nitrilomethylidene)]diphenolato}(thiocyanato)iron(III)), [Fe(C
17H
16N
2O
2)(NCS)(H
2O)], has been synthesized and characterized. It is a mononuclear compound. The Fe
III atom has a slightly distorted octahedral geometry, coordinated by two N and two O donors of
L [
L is the
N,
N′-bis(2-hydroxyphenylmethyleneimino)-1,3-diaminopropane anion] and one N atom from a thiocyanate anion, together with a water molecule. In the crystal structure, the molecules are held together by intermolecular O—H
O hydrogen bonds, forming chains extending in the
b direction.
Supporting information
CCDC reference: 233771
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.011 Å
- R factor = 0.058
- wR factor = 0.137
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.108
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.71
PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 5.67 su
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C10
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C14
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C18
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11
PLAT731_ALERT_1_C Bond Calc 0.89(3), Rep 0.896(11) ...... 2.73 su-Rat
O3 -H17 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.89(4), Rep 0.896(11) ...... 3.64 su-Rat
O3 -H18 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.89(3), Rep 0.900(10) ...... 3.00 su-Rat
O3 -H17 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.89(4), Rep 0.900(10) ...... 4.00 su-Rat
O3 -H18 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
13 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
aqua{2,2'-[propane-1,3-
diylbis(nitrilomethylidene)]diphenolato}(thiocyanato)iron(III))
top
Crystal data top
[Fe(C17H16N2O2)(NCS)(H2O)] | F(000) = 852 |
Mr = 412.26 | Dx = 1.490 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1105 reflections |
a = 12.82 (5) Å | θ = 3.1–19.0° |
b = 6.96 (2) Å | µ = 0.96 mm−1 |
c = 21.49 (7) Å | T = 298 K |
β = 106.51 (6)° | Block, brown |
V = 1838 (11) Å3 | 0.23 × 0.14 × 0.05 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 3246 independent reflections |
Radiation source: fine-focus sealed tube | 1452 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.108 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→15 |
Tmin = 0.810, Tmax = 0.954 | k = −6→8 |
9280 measured reflections | l = −25→23 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.85 | w = 1/[σ2(Fo2) + (0.0552P)2] where P = (Fo2 + 2Fc2)/3 |
3246 reflections | (Δ/σ)max < 0.001 |
243 parameters | Δρmax = 0.72 e Å−3 |
3 restraints | Δρmin = −0.26 e Å−3 |
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 F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 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 | Uiso*/Ueq | |
Fe1 | 0.09534 (7) | 0.40125 (11) | 0.16927 (4) | 0.0510 (3) | |
N1 | −0.0043 (4) | 0.6093 (6) | 0.1972 (2) | 0.0544 (12) | |
N2 | 0.1178 (4) | 0.5738 (6) | 0.0912 (2) | 0.0556 (13) | |
N3 | −0.0441 (4) | 0.2832 (6) | 0.1120 (2) | 0.0563 (14) | |
O1 | 0.0907 (3) | 0.2590 (5) | 0.24706 (16) | 0.0533 (10) | |
O2 | 0.1952 (3) | 0.2186 (5) | 0.15053 (18) | 0.0636 (11) | |
O3 | 0.2255 (4) | 0.5574 (7) | 0.22788 (19) | 0.0744 (13) | |
S1 | −0.25974 (17) | 0.1886 (3) | 0.08575 (10) | 0.1016 (7) | |
C1 | 0.0084 (5) | 0.2475 (8) | 0.2744 (3) | 0.0501 (15) | |
C2 | 0.0019 (5) | 0.0854 (9) | 0.3117 (3) | 0.0640 (17) | |
H2 | 0.0523 | −0.0133 | 0.3158 | 0.077* | |
C3 | −0.0796 (5) | 0.0706 (10) | 0.3429 (3) | 0.0732 (19) | |
H3 | −0.0837 | −0.0394 | 0.3666 | 0.088* | |
C4 | −0.1531 (6) | 0.2146 (13) | 0.3390 (3) | 0.082 (2) | |
H4 | −0.2065 | 0.2041 | 0.3605 | 0.099* | |
C5 | −0.1474 (5) | 0.3750 (10) | 0.3032 (3) | 0.0699 (18) | |
H5 | −0.1975 | 0.4735 | 0.3007 | 0.084* | |
C6 | −0.0674 (5) | 0.3948 (8) | 0.2699 (3) | 0.0504 (14) | |
C7 | −0.0648 (5) | 0.5693 (8) | 0.2352 (3) | 0.0560 (16) | |
H7 | −0.1119 | 0.6659 | 0.2403 | 0.067* | |
C8 | −0.0184 (5) | 0.7986 (8) | 0.1659 (3) | 0.0707 (18) | |
H8A | 0.0468 | 0.8746 | 0.1833 | 0.085* | |
H8B | −0.0786 | 0.8650 | 0.1754 | 0.085* | |
C9 | −0.0406 (6) | 0.7800 (8) | 0.0923 (3) | 0.079 (2) | |
H9A | −0.0880 | 0.6706 | 0.0775 | 0.094* | |
H9B | −0.0789 | 0.8939 | 0.0718 | 0.094* | |
C10 | 0.0593 (6) | 0.7553 (8) | 0.0703 (3) | 0.083 (2) | |
H10A | 0.0388 | 0.7617 | 0.0233 | 0.100* | |
H10B | 0.1083 | 0.8615 | 0.0869 | 0.100* | |
C11 | 0.1880 (5) | 0.5324 (9) | 0.0599 (3) | 0.0630 (18) | |
H11 | 0.1926 | 0.6196 | 0.0280 | 0.076* | |
C12 | 0.2590 (5) | 0.3706 (9) | 0.0682 (3) | 0.0583 (16) | |
C13 | 0.3327 (6) | 0.3610 (12) | 0.0290 (3) | 0.086 (2) | |
H13 | 0.3322 | 0.4607 | 0.0001 | 0.103* | |
C14 | 0.4027 (7) | 0.2137 (14) | 0.0322 (4) | 0.107 (3) | |
H14 | 0.4504 | 0.2123 | 0.0067 | 0.129* | |
C15 | 0.4010 (6) | 0.0649 (12) | 0.0746 (3) | 0.096 (3) | |
H15 | 0.4486 | −0.0378 | 0.0776 | 0.115* | |
C16 | 0.3298 (5) | 0.0647 (10) | 0.1133 (3) | 0.074 (2) | |
H16 | 0.3291 | −0.0393 | 0.1403 | 0.089* | |
C17 | 0.2603 (5) | 0.2183 (9) | 0.1116 (3) | 0.0581 (16) | |
C18 | −0.1334 (6) | 0.2475 (8) | 0.1026 (3) | 0.0534 (16) | |
H17 | 0.222 (4) | 0.591 (8) | 0.2674 (14) | 0.10 (2)* | |
H18 | 0.288 (3) | 0.601 (8) | 0.223 (2) | 0.09 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0564 (6) | 0.0456 (5) | 0.0503 (5) | 0.0016 (5) | 0.0140 (4) | −0.0002 (4) |
N1 | 0.067 (4) | 0.040 (3) | 0.053 (3) | −0.001 (3) | 0.011 (3) | −0.005 (2) |
N2 | 0.073 (4) | 0.040 (3) | 0.053 (3) | −0.001 (3) | 0.017 (3) | −0.001 (2) |
N3 | 0.068 (4) | 0.043 (3) | 0.055 (3) | −0.011 (3) | 0.014 (3) | −0.001 (2) |
O1 | 0.054 (3) | 0.055 (2) | 0.053 (2) | 0.009 (2) | 0.019 (2) | 0.0096 (18) |
O2 | 0.076 (3) | 0.060 (3) | 0.059 (2) | 0.018 (2) | 0.027 (2) | 0.010 (2) |
O3 | 0.064 (3) | 0.106 (4) | 0.054 (3) | −0.040 (3) | 0.020 (2) | −0.018 (3) |
S1 | 0.0756 (16) | 0.1067 (15) | 0.1213 (17) | −0.0079 (12) | 0.0257 (13) | 0.0229 (14) |
C1 | 0.050 (4) | 0.060 (4) | 0.040 (3) | −0.005 (3) | 0.011 (3) | −0.002 (3) |
C2 | 0.064 (5) | 0.070 (4) | 0.061 (4) | 0.005 (4) | 0.022 (4) | 0.002 (4) |
C3 | 0.068 (5) | 0.088 (5) | 0.065 (4) | −0.007 (4) | 0.022 (4) | 0.018 (4) |
C4 | 0.052 (5) | 0.121 (6) | 0.078 (5) | −0.009 (5) | 0.026 (4) | 0.010 (5) |
C5 | 0.053 (4) | 0.095 (5) | 0.065 (4) | 0.009 (4) | 0.022 (4) | −0.004 (4) |
C6 | 0.044 (4) | 0.057 (4) | 0.048 (3) | 0.005 (3) | 0.010 (3) | −0.006 (3) |
C7 | 0.054 (4) | 0.056 (4) | 0.054 (4) | 0.009 (3) | 0.009 (3) | −0.009 (3) |
C8 | 0.089 (5) | 0.042 (4) | 0.082 (5) | 0.006 (3) | 0.026 (4) | −0.006 (3) |
C9 | 0.119 (7) | 0.040 (4) | 0.062 (4) | 0.020 (4) | 0.001 (4) | 0.005 (3) |
C10 | 0.122 (7) | 0.058 (4) | 0.082 (5) | 0.016 (4) | 0.047 (5) | 0.010 (4) |
C11 | 0.086 (5) | 0.062 (4) | 0.040 (3) | −0.012 (4) | 0.015 (4) | 0.004 (3) |
C12 | 0.058 (4) | 0.072 (4) | 0.042 (3) | 0.005 (4) | 0.010 (3) | 0.005 (3) |
C13 | 0.086 (6) | 0.123 (7) | 0.053 (4) | −0.004 (5) | 0.027 (4) | 0.006 (4) |
C14 | 0.091 (7) | 0.155 (8) | 0.081 (6) | 0.030 (6) | 0.034 (5) | 0.004 (6) |
C15 | 0.089 (6) | 0.135 (7) | 0.066 (4) | 0.054 (5) | 0.026 (4) | 0.011 (5) |
C16 | 0.074 (5) | 0.095 (5) | 0.057 (4) | 0.033 (4) | 0.021 (4) | 0.003 (4) |
C17 | 0.058 (5) | 0.074 (4) | 0.040 (3) | 0.006 (4) | 0.011 (3) | 0.003 (3) |
C18 | 0.075 (5) | 0.040 (3) | 0.048 (4) | 0.000 (3) | 0.023 (4) | 0.005 (3) |
Geometric parameters (Å, º) top
Fe1—O2 | 1.926 (6) | C5—C6 | 1.415 (8) |
Fe1—O1 | 1.958 (6) | C5—H5 | 0.93 |
Fe1—N3 | 2.034 (7) | C6—C7 | 1.431 (8) |
Fe1—O3 | 2.088 (6) | C7—H7 | 0.93 |
Fe1—N1 | 2.128 (7) | C8—C9 | 1.530 (9) |
Fe1—N2 | 2.148 (7) | C8—H8A | 0.97 |
N1—C7 | 1.305 (7) | C8—H8B | 0.97 |
N1—C8 | 1.467 (8) | C9—C10 | 1.495 (9) |
N2—C11 | 1.299 (7) | C9—H9A | 0.97 |
N2—C10 | 1.472 (8) | C9—H9B | 0.97 |
N3—C18 | 1.132 (8) | C10—H10A | 0.97 |
O1—C1 | 1.348 (7) | C10—H10B | 0.97 |
O2—C17 | 1.339 (7) | C11—C12 | 1.427 (9) |
O3—H17 | 0.896 (11) | C11—H11 | 0.93 |
O3—H18 | 0.896 (11) | C12—C17 | 1.409 (8) |
S1—C18 | 1.610 (9) | C12—C13 | 1.435 (9) |
C1—C6 | 1.397 (8) | C13—C14 | 1.352 (10) |
C1—C2 | 1.400 (8) | C13—H13 | 0.93 |
C2—C3 | 1.395 (8) | C14—C15 | 1.384 (10) |
C2—H2 | 0.93 | C14—H14 | 0.93 |
C3—C4 | 1.363 (9) | C15—C16 | 1.398 (8) |
C3—H3 | 0.93 | C15—H15 | 0.93 |
C4—C5 | 1.369 (9) | C16—C17 | 1.385 (8) |
C4—H4 | 0.93 | C16—H16 | 0.93 |
| | | |
O2—Fe1—O1 | 91.6 (2) | C5—C6—C7 | 118.3 (6) |
O2—Fe1—N3 | 97.4 (3) | N1—C7—C6 | 127.8 (5) |
O1—Fe1—N3 | 94.5 (3) | N1—C7—H7 | 116.1 |
O2—Fe1—O3 | 90.3 (3) | C6—C7—H7 | 116.1 |
O1—Fe1—O3 | 87.8 (3) | N1—C8—C9 | 111.2 (5) |
N3—Fe1—O3 | 171.9 (2) | N1—C8—H8A | 109.4 |
O2—Fe1—N1 | 175.13 (17) | C9—C8—H8A | 109.4 |
O1—Fe1—N1 | 86.4 (3) | N1—C8—H8B | 109.4 |
N3—Fe1—N1 | 87.1 (3) | C9—C8—H8B | 109.4 |
O3—Fe1—N1 | 85.2 (3) | H8A—C8—H8B | 108.0 |
O2—Fe1—N2 | 87.7 (3) | C10—C9—C8 | 114.3 (6) |
O1—Fe1—N2 | 173.07 (17) | C10—C9—H9A | 108.7 |
N3—Fe1—N2 | 92.5 (3) | C8—C9—H9A | 108.7 |
O3—Fe1—N2 | 85.3 (3) | C10—C9—H9B | 108.7 |
N1—Fe1—N2 | 93.7 (3) | C8—C9—H9B | 108.7 |
C7—N1—C8 | 117.5 (5) | H9A—C9—H9B | 107.6 |
C7—N1—Fe1 | 122.9 (4) | N2—C10—C9 | 114.3 (5) |
C8—N1—Fe1 | 119.1 (4) | N2—C10—H10A | 108.7 |
C11—N2—C10 | 113.6 (5) | C9—C10—H10A | 108.7 |
C11—N2—Fe1 | 123.1 (4) | N2—C10—H10B | 108.7 |
C10—N2—Fe1 | 123.2 (4) | C9—C10—H10B | 108.7 |
C18—N3—Fe1 | 150.1 (5) | H10A—C10—H10B | 107.6 |
C1—O1—Fe1 | 128.3 (4) | N2—C11—C12 | 128.5 (6) |
C17—O2—Fe1 | 134.5 (4) | N2—C11—H11 | 115.8 |
Fe1—O3—H17 | 117 (3) | C12—C11—H11 | 115.8 |
Fe1—O3—H18 | 134 (3) | C17—C12—C11 | 124.3 (6) |
H17—O3—H18 | 109 (2) | C17—C12—C13 | 117.9 (6) |
O1—C1—C6 | 122.8 (5) | C11—C12—C13 | 117.8 (6) |
O1—C1—C2 | 118.7 (5) | C14—C13—C12 | 123.0 (7) |
C6—C1—C2 | 118.5 (6) | C14—C13—H13 | 118.5 |
C3—C2—C1 | 120.6 (6) | C12—C13—H13 | 118.5 |
C3—C2—H2 | 119.7 | C13—C14—C15 | 117.8 (8) |
C1—C2—H2 | 119.7 | C13—C14—H14 | 121.1 |
C4—C3—C2 | 121.1 (6) | C15—C14—H14 | 121.1 |
C4—C3—H3 | 119.4 | C14—C15—C16 | 121.8 (7) |
C2—C3—H3 | 119.4 | C14—C15—H15 | 119.1 |
C3—C4—C5 | 119.1 (6) | C16—C15—H15 | 119.1 |
C3—C4—H4 | 120.5 | C17—C16—C15 | 120.5 (6) |
C5—C4—H4 | 120.5 | C17—C16—H16 | 119.7 |
C4—C5—C6 | 121.7 (6) | C15—C16—H16 | 119.7 |
C4—C5—H5 | 119.1 | O2—C17—C16 | 119.7 (6) |
C6—C5—H5 | 119.1 | O2—C17—C12 | 121.3 (6) |
C1—C6—C5 | 118.9 (6) | C16—C17—C12 | 118.9 (6) |
C1—C6—C7 | 122.7 (6) | N3—C18—S1 | 176.6 (6) |
| | | |
O1—Fe1—N1—C7 | −22.5 (4) | C3—C4—C5—C6 | 0.2 (10) |
N3—Fe1—N1—C7 | 72.2 (5) | O1—C1—C6—C5 | −176.5 (5) |
O3—Fe1—N1—C7 | −110.6 (5) | C2—C1—C6—C5 | 0.2 (8) |
N2—Fe1—N1—C7 | 164.4 (4) | O1—C1—C6—C7 | 0.7 (8) |
O1—Fe1—N1—C8 | 166.3 (4) | C2—C1—C6—C7 | 177.4 (5) |
N3—Fe1—N1—C8 | −99.0 (5) | C4—C5—C6—C1 | −0.8 (9) |
O3—Fe1—N1—C8 | 78.3 (5) | C4—C5—C6—C7 | −178.1 (6) |
N2—Fe1—N1—C8 | −6.7 (4) | C8—N1—C7—C6 | 178.8 (5) |
O2—Fe1—N2—C11 | −6.0 (5) | Fe1—N1—C7—C6 | 7.5 (8) |
N3—Fe1—N2—C11 | −103.3 (5) | C1—C6—C7—N1 | 9.1 (9) |
O3—Fe1—N2—C11 | 84.5 (5) | C5—C6—C7—N1 | −173.7 (5) |
N1—Fe1—N2—C11 | 169.4 (4) | C7—N1—C8—C9 | −126.5 (6) |
O2—Fe1—N2—C10 | 177.3 (5) | Fe1—N1—C8—C9 | 45.2 (7) |
N3—Fe1—N2—C10 | 79.9 (5) | N1—C8—C9—C10 | −82.5 (7) |
O3—Fe1—N2—C10 | −92.3 (5) | C11—N2—C10—C9 | 164.6 (6) |
N1—Fe1—N2—C10 | −7.4 (5) | Fe1—N2—C10—C9 | −18.4 (7) |
O2—Fe1—N3—C18 | 145.0 (10) | C8—C9—C10—N2 | 65.9 (7) |
O1—Fe1—N3—C18 | 52.8 (10) | C10—N2—C11—C12 | 179.1 (6) |
N1—Fe1—N3—C18 | −33.4 (10) | Fe1—N2—C11—C12 | 2.1 (9) |
N2—Fe1—N3—C18 | −127.0 (10) | N2—C11—C12—C17 | 3.3 (10) |
O2—Fe1—O1—C1 | −150.6 (4) | N2—C11—C12—C13 | −177.6 (6) |
N3—Fe1—O1—C1 | −53.1 (5) | C17—C12—C13—C14 | −0.2 (10) |
O3—Fe1—O1—C1 | 119.2 (5) | C11—C12—C13—C14 | −179.3 (7) |
N1—Fe1—O1—C1 | 33.8 (4) | C12—C13—C14—C15 | 1.1 (12) |
O1—Fe1—O2—C17 | −164.9 (5) | C13—C14—C15—C16 | 0.0 (12) |
N3—Fe1—O2—C17 | 100.4 (6) | C14—C15—C16—C17 | −2.0 (11) |
O3—Fe1—O2—C17 | −77.1 (6) | Fe1—O2—C17—C16 | 175.0 (4) |
N2—Fe1—O2—C17 | 8.2 (5) | Fe1—O2—C17—C12 | −5.7 (8) |
Fe1—O1—C1—C6 | −29.1 (7) | C15—C16—C17—O2 | −177.8 (6) |
Fe1—O1—C1—C2 | 154.2 (4) | C15—C16—C17—C12 | 2.9 (9) |
O1—C1—C2—C3 | 177.7 (5) | C11—C12—C17—O2 | −2.1 (9) |
C6—C1—C2—C3 | 0.8 (8) | C13—C12—C17—O2 | 178.9 (5) |
C1—C2—C3—C4 | −1.4 (9) | C11—C12—C17—C16 | 177.2 (6) |
C2—C3—C4—C5 | 0.9 (10) | C13—C12—C17—C16 | −1.8 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H17···O2i | 0.90 (1) | 1.99 (3) | 2.758 (9) | 143 (4) |
O3—H18···O1i | 0.90 (1) | 1.86 (3) | 2.663 (9) | 148 (4) |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |