The title compound, [Fe(C17H16N2O2)(N3)], is mononuclear. The FeIII atom is coordinated by four atoms from one Schiff base ligand and one N atom from an azide anion. In the crystal structure, the molecules are held together by hydrogen bonds, forming chains extending in the a direction.
Supporting information
CCDC reference: 245111
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.008 Å
- R factor = 0.072
- wR factor = 0.225
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.16
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.10 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... N5'
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N4
PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C9 - C17 ... 1.40 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.00 Deg.
N5 -N4 -N5' 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
11 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
6 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
1 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.
Azido[bis(2-oxidophenylmethyleneimino)propane-1,2-diamine(2-)]iron(III)
top
Crystal data top
[Fe(C17H16N2O2)(N3)] | F(000) = 780 |
Mr = 378.20 | Dx = 1.497 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7388 (8) Å | Cell parameters from 3662 reflections |
b = 13.7957 (13) Å | θ = 4–27° |
c = 14.4499 (14) Å | µ = 0.92 mm−1 |
β = 105.620 (2)° | T = 298 K |
V = 1677.7 (3) Å3 | Block, black |
Z = 4 | 0.18 × 0.18 × 0.10 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 3528 independent reflections |
Radiation source: fine-focus sealed tube | 2159 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
φ and ω scans | θmax = 27.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −5→11 |
Tmin = 0.852, Tmax = 0.914 | k = −17→17 |
9418 measured reflections | l = −18→18 |
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)] = 0.072 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.225 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.1146P)2 + 0.6771P] where P = (Fo2 + 2Fc2)/3 |
3528 reflections | (Δ/σ)max = 0.009 |
236 parameters | Δρmax = 0.86 e Å−3 |
0 restraints | Δρmin = −0.40 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 | Occ. (<1) |
Fe1 | 0.14566 (9) | 0.99429 (4) | 0.10846 (5) | 0.0514 (3) | |
C1 | −0.0778 (6) | 0.8059 (3) | 0.1059 (3) | 0.0533 (12) | |
C2 | 0.0094 (6) | 0.8133 (3) | 0.0353 (4) | 0.0496 (12) | |
C3 | 0.0271 (7) | 0.7310 (4) | −0.0147 (4) | 0.0585 (13) | |
H3 | 0.0810 | 0.7354 | −0.0619 | 0.070* | |
C4 | −0.0314 (8) | 0.6424 (4) | 0.0028 (4) | 0.0741 (17) | |
H4 | −0.0162 | 0.5880 | −0.0317 | 0.089* | |
C5 | −0.1118 (9) | 0.6342 (4) | 0.0727 (5) | 0.087 (2) | |
H5 | −0.1494 | 0.5742 | 0.0860 | 0.104* | |
C6 | −0.1375 (8) | 0.7162 (4) | 0.1224 (4) | 0.0731 (17) | |
H6 | −0.1950 | 0.7108 | 0.1677 | 0.088* | |
C7 | −0.1111 (7) | 0.8893 (4) | 0.1572 (4) | 0.0590 (13) | |
H7 | −0.1911 | 0.8843 | 0.1883 | 0.071* | |
C8 | −0.0902 (8) | 1.0568 (4) | 0.2064 (5) | 0.0744 (17) | |
H8A | −0.1471 | 1.0374 | 0.2525 | 0.089* | |
H8B | −0.1591 | 1.0977 | 0.1581 | 0.089* | |
C9 | 0.0630 (11) | 1.1096 (5) | 0.2571 (4) | 0.092 (2) | |
H9 | 0.0352 | 1.1768 | 0.2672 | 0.111* | |
C10 | 0.2561 (7) | 1.1846 (4) | 0.1883 (3) | 0.0584 (14) | |
H10 | 0.2541 | 1.2357 | 0.2299 | 0.070* | |
C11 | 0.3598 (7) | 1.1937 (3) | 0.1264 (3) | 0.0541 (13) | |
C12 | 0.3777 (6) | 1.1210 (3) | 0.0605 (3) | 0.0480 (11) | |
C13 | 0.4835 (6) | 1.1369 (4) | 0.0050 (4) | 0.0588 (14) | |
H13 | 0.4975 | 1.0893 | −0.0375 | 0.071* | |
C14 | 0.5665 (8) | 1.2214 (4) | 0.0122 (5) | 0.0754 (17) | |
H14 | 0.6373 | 1.2295 | −0.0251 | 0.091* | |
C15 | 0.5483 (9) | 1.2953 (5) | 0.0725 (5) | 0.091 (2) | |
H15 | 0.6050 | 1.3529 | 0.0759 | 0.109* | |
C16 | 0.4444 (8) | 1.2807 (4) | 0.1277 (4) | 0.0759 (18) | |
H16 | 0.4295 | 1.3305 | 0.1678 | 0.091* | |
C17 | 0.1371 (15) | 1.0701 (7) | 0.3470 (7) | 0.149 (4) | |
H17A | 0.1771 | 1.0069 | 0.3383 | 0.223* | |
H17B | 0.0608 | 1.0648 | 0.3837 | 0.223* | |
H17C | 0.2234 | 1.1108 | 0.3806 | 0.223* | |
N1 | −0.0374 (6) | 0.9706 (3) | 0.1623 (3) | 0.0550 (11) | |
N2 | 0.1674 (6) | 1.1111 (3) | 0.1908 (3) | 0.0583 (12) | |
N3 | 0.2972 (7) | 0.9007 (3) | 0.2108 (3) | 0.0670 (13) | |
N4 | 0.4371 (8) | 0.8997 (4) | 0.2381 (3) | 0.0662 (13) | |
N5 | 0.570 (5) | 0.914 (4) | 0.275 (2) | 0.094 (7) | 0.50 (18) |
N5' | 0.574 (4) | 0.878 (10) | 0.259 (5) | 0.100 (19) | 0.50 (18) |
O1 | 0.0632 (4) | 0.8979 (2) | 0.0133 (2) | 0.0487 (8) | |
O2 | 0.2979 (4) | 1.0389 (2) | 0.0498 (2) | 0.0521 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0631 (6) | 0.0411 (4) | 0.0548 (5) | −0.0008 (3) | 0.0239 (4) | −0.0022 (3) |
C1 | 0.049 (3) | 0.054 (3) | 0.056 (3) | 0.001 (2) | 0.012 (3) | 0.012 (2) |
C2 | 0.048 (3) | 0.044 (3) | 0.054 (3) | 0.003 (2) | 0.008 (2) | 0.008 (2) |
C3 | 0.052 (3) | 0.044 (3) | 0.077 (3) | −0.001 (2) | 0.014 (3) | −0.004 (2) |
C4 | 0.079 (5) | 0.044 (3) | 0.096 (4) | −0.002 (3) | 0.019 (4) | 0.012 (3) |
C5 | 0.090 (5) | 0.048 (3) | 0.114 (5) | −0.012 (3) | 0.014 (4) | 0.019 (3) |
C6 | 0.073 (4) | 0.075 (4) | 0.072 (4) | −0.014 (3) | 0.020 (3) | 0.023 (3) |
C7 | 0.060 (4) | 0.064 (3) | 0.055 (3) | −0.001 (3) | 0.019 (3) | 0.012 (2) |
C8 | 0.083 (5) | 0.066 (3) | 0.089 (4) | −0.004 (3) | 0.048 (4) | −0.014 (3) |
C9 | 0.161 (8) | 0.077 (4) | 0.059 (4) | 0.014 (5) | 0.063 (5) | −0.003 (3) |
C10 | 0.072 (4) | 0.051 (3) | 0.049 (3) | 0.006 (3) | 0.011 (3) | −0.009 (2) |
C11 | 0.055 (3) | 0.045 (3) | 0.054 (3) | −0.003 (2) | 0.001 (3) | −0.007 (2) |
C12 | 0.047 (3) | 0.038 (2) | 0.054 (3) | 0.003 (2) | 0.005 (2) | 0.0023 (19) |
C13 | 0.052 (3) | 0.049 (3) | 0.080 (4) | 0.001 (2) | 0.027 (3) | 0.000 (2) |
C14 | 0.066 (4) | 0.069 (4) | 0.097 (4) | −0.008 (3) | 0.030 (4) | 0.005 (3) |
C15 | 0.093 (5) | 0.063 (4) | 0.112 (5) | −0.037 (4) | 0.019 (5) | −0.008 (4) |
C16 | 0.089 (5) | 0.048 (3) | 0.083 (4) | −0.018 (3) | 0.010 (4) | −0.018 (3) |
C17 | 0.162 (11) | 0.142 (8) | 0.142 (8) | −0.012 (8) | 0.040 (8) | −0.036 (7) |
N1 | 0.063 (3) | 0.057 (2) | 0.053 (2) | 0.007 (2) | 0.029 (2) | 0.0046 (19) |
N2 | 0.081 (3) | 0.043 (2) | 0.053 (2) | 0.002 (2) | 0.023 (2) | −0.0063 (17) |
N3 | 0.063 (3) | 0.055 (3) | 0.082 (3) | 0.007 (3) | 0.018 (3) | 0.017 (2) |
N4 | 0.079 (4) | 0.065 (3) | 0.060 (3) | 0.006 (3) | 0.027 (3) | 0.008 (2) |
N5 | 0.051 (13) | 0.112 (15) | 0.110 (16) | 0.005 (10) | 0.009 (12) | −0.03 (2) |
N5' | 0.066 (12) | 0.15 (4) | 0.091 (19) | 0.017 (16) | 0.040 (11) | 0.04 (2) |
O1 | 0.059 (2) | 0.0396 (16) | 0.0532 (18) | −0.0070 (16) | 0.0240 (17) | −0.0032 (13) |
O2 | 0.062 (2) | 0.0376 (16) | 0.065 (2) | −0.0040 (16) | 0.0300 (18) | −0.0082 (14) |
Geometric parameters (Å, º) top
Fe1—O2 | 1.864 (3) | C9—C17 | 1.396 (11) |
Fe1—O1 | 1.909 (3) | C9—N2 | 1.490 (7) |
Fe1—N2 | 1.981 (4) | C9—H9 | 0.9800 |
Fe1—N1 | 1.985 (4) | C10—N2 | 1.283 (7) |
Fe1—N3 | 2.134 (5) | C10—C11 | 1.439 (7) |
C1—C6 | 1.388 (7) | C10—H10 | 0.9301 |
C1—C2 | 1.431 (7) | C11—C16 | 1.408 (7) |
C1—C7 | 1.440 (7) | C11—C12 | 1.422 (6) |
C2—O1 | 1.329 (5) | C12—O2 | 1.316 (5) |
C2—C3 | 1.377 (7) | C12—C13 | 1.394 (7) |
C3—C4 | 1.375 (7) | C13—C14 | 1.363 (8) |
C3—H3 | 0.9301 | C13—H13 | 0.9301 |
C4—C5 | 1.381 (9) | C14—C15 | 1.378 (9) |
C4—H4 | 0.9301 | C14—H14 | 0.9299 |
C5—C6 | 1.390 (9) | C15—C16 | 1.376 (9) |
C5—H5 | 0.9300 | C15—H15 | 0.9299 |
C6—H6 | 0.9300 | C16—H16 | 0.9300 |
C7—N1 | 1.285 (6) | C17—H17A | 0.9601 |
C7—H7 | 0.9300 | C17—H17B | 0.9601 |
C8—N1 | 1.482 (7) | C17—H17C | 0.9600 |
C8—C9 | 1.527 (10) | N3—N4 | 1.179 (7) |
C8—H8A | 0.9700 | N4—N5 | 1.16 (4) |
C8—H8B | 0.9700 | N4—N5' | 1.19 (4) |
| | | |
O2—Fe1—O1 | 94.59 (13) | N2—C9—H9 | 107.6 |
O2—Fe1—N2 | 92.26 (16) | C8—C9—H9 | 107.6 |
O1—Fe1—N2 | 162.84 (18) | N2—C10—C11 | 125.0 (4) |
O2—Fe1—N1 | 169.01 (15) | N2—C10—H10 | 117.6 |
O1—Fe1—N1 | 88.83 (16) | C11—C10—H10 | 117.4 |
N2—Fe1—N1 | 81.73 (19) | C16—C11—C12 | 117.3 (5) |
O2—Fe1—N3 | 97.43 (18) | C16—C11—C10 | 118.9 (5) |
O1—Fe1—N3 | 96.95 (17) | C12—C11—C10 | 123.8 (5) |
N2—Fe1—N3 | 97.74 (19) | O2—C12—C13 | 118.8 (4) |
N1—Fe1—N3 | 92.51 (19) | O2—C12—C11 | 122.3 (5) |
C6—C1—C2 | 118.8 (5) | C13—C12—C11 | 118.9 (4) |
C6—C1—C7 | 119.1 (5) | C14—C13—C12 | 120.9 (5) |
C2—C1—C7 | 122.0 (4) | C14—C13—H13 | 119.6 |
O1—C2—C3 | 120.1 (4) | C12—C13—H13 | 119.5 |
O1—C2—C1 | 121.6 (4) | C13—C14—C15 | 122.1 (6) |
C3—C2—C1 | 118.2 (5) | C13—C14—H14 | 118.8 |
C4—C3—C2 | 122.5 (5) | C15—C14—H14 | 119.1 |
C4—C3—H3 | 118.7 | C16—C15—C14 | 117.7 (6) |
C2—C3—H3 | 118.9 | C16—C15—H15 | 121.3 |
C3—C4—C5 | 119.6 (6) | C14—C15—H15 | 121.0 |
C3—C4—H4 | 120.3 | C15—C16—C11 | 123.0 (6) |
C5—C4—H4 | 120.1 | C15—C16—H16 | 118.6 |
C4—C5—C6 | 119.7 (5) | C11—C16—H16 | 118.5 |
C4—C5—H5 | 120.1 | C9—C17—H17A | 109.0 |
C6—C5—H5 | 120.2 | C9—C17—H17B | 109.1 |
C5—C6—C1 | 121.1 (6) | H17A—C17—H17B | 109.5 |
C5—C6—H6 | 119.4 | C9—C17—H17C | 110.3 |
C1—C6—H6 | 119.5 | H17A—C17—H17C | 109.5 |
N1—C7—C1 | 124.0 (5) | H17B—C17—H17C | 109.5 |
N1—C7—H7 | 117.9 | C7—N1—C8 | 121.1 (5) |
C1—C7—H7 | 118.1 | C7—N1—Fe1 | 124.5 (4) |
N1—C8—C9 | 104.8 (5) | C8—N1—Fe1 | 114.4 (4) |
N1—C8—H8A | 110.6 | C10—N2—C9 | 120.6 (5) |
C9—C8—H8A | 110.3 | C10—N2—Fe1 | 125.9 (4) |
N1—C8—H8B | 111.2 | C9—N2—Fe1 | 113.5 (4) |
C9—C8—H8B | 111.2 | N4—N3—Fe1 | 129.2 (4) |
H8A—C8—H8B | 108.7 | N5—N4—N3 | 167 (3) |
C17—C9—N2 | 113.1 (8) | N5—N4—N5' | 27 (5) |
C17—C9—C8 | 112.8 (7) | N3—N4—N5' | 166 (7) |
N2—C9—C8 | 107.9 (5) | C2—O1—Fe1 | 121.9 (3) |
C17—C9—H9 | 107.6 | C12—O2—Fe1 | 130.7 (3) |
| | | |
C6—C1—C2—O1 | 176.9 (5) | O2—Fe1—N1—C8 | −40.3 (10) |
C7—C1—C2—O1 | −0.4 (8) | O1—Fe1—N1—C8 | −148.6 (4) |
C6—C1—C2—C3 | 1.4 (7) | N2—Fe1—N1—C8 | 17.0 (4) |
C7—C1—C2—C3 | −175.9 (5) | N3—Fe1—N1—C8 | 114.5 (4) |
O1—C2—C3—C4 | −177.6 (5) | C11—C10—N2—C9 | −179.4 (5) |
C1—C2—C3—C4 | −2.0 (8) | C11—C10—N2—Fe1 | −1.9 (8) |
C2—C3—C4—C5 | 0.2 (9) | C17—C9—N2—C10 | −90.2 (8) |
C3—C4—C5—C6 | 2.2 (10) | C8—C9—N2—C10 | 144.3 (6) |
C4—C5—C6—C1 | −2.8 (10) | C17—C9—N2—Fe1 | 92.1 (7) |
C2—C1—C6—C5 | 1.0 (9) | C8—C9—N2—Fe1 | −33.4 (6) |
C7—C1—C6—C5 | 178.4 (6) | O2—Fe1—N2—C10 | 3.1 (5) |
C6—C1—C7—N1 | 165.6 (5) | O1—Fe1—N2—C10 | −110.4 (6) |
C2—C1—C7—N1 | −17.1 (8) | N1—Fe1—N2—C10 | −167.7 (5) |
N1—C8—C9—C17 | −81.5 (7) | N3—Fe1—N2—C10 | 100.9 (5) |
N1—C8—C9—N2 | 44.2 (6) | O2—Fe1—N2—C9 | −179.3 (4) |
N2—C10—C11—C16 | 176.7 (5) | O1—Fe1—N2—C9 | 67.2 (7) |
N2—C10—C11—C12 | −0.7 (9) | N1—Fe1—N2—C9 | 9.9 (4) |
C16—C11—C12—O2 | −176.5 (5) | N3—Fe1—N2—C9 | −81.5 (4) |
C10—C11—C12—O2 | 1.0 (8) | O2—Fe1—N3—N4 | 18.4 (6) |
C16—C11—C12—C13 | 3.6 (7) | O1—Fe1—N3—N4 | 114.0 (6) |
C10—C11—C12—C13 | −179.0 (5) | N2—Fe1—N3—N4 | −74.9 (6) |
O2—C12—C13—C14 | 178.8 (5) | N1—Fe1—N3—N4 | −156.9 (6) |
C11—C12—C13—C14 | −1.3 (8) | Fe1—N3—N4—N5 | 76 (8) |
C12—C13—C14—C15 | −1.2 (10) | Fe1—N3—N4—N5' | −124 (7) |
C13—C14—C15—C16 | 1.2 (11) | C3—C2—O1—Fe1 | −146.6 (4) |
C14—C15—C16—C11 | 1.3 (10) | C1—C2—O1—Fe1 | 37.9 (6) |
C12—C11—C16—C15 | −3.7 (9) | O2—Fe1—O1—C2 | 145.7 (4) |
C10—C11—C16—C15 | 178.8 (6) | N2—Fe1—O1—C2 | −101.1 (6) |
C1—C7—N1—C8 | 172.7 (5) | N1—Fe1—O1—C2 | −44.8 (4) |
C1—C7—N1—Fe1 | −4.4 (7) | N3—Fe1—O1—C2 | 47.6 (4) |
C9—C8—N1—C7 | 144.4 (5) | C13—C12—O2—Fe1 | −178.5 (3) |
C9—C8—N1—Fe1 | −38.3 (5) | C11—C12—O2—Fe1 | 1.6 (7) |
O2—Fe1—N1—C7 | 137.0 (7) | O1—Fe1—O2—C12 | 161.3 (4) |
O1—Fe1—N1—C7 | 28.6 (4) | N2—Fe1—O2—C12 | −3.0 (4) |
N2—Fe1—N1—C7 | −165.7 (5) | N1—Fe1—O2—C12 | 53.5 (10) |
N3—Fe1—N1—C7 | −68.3 (5) | N3—Fe1—O2—C12 | −101.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···N5′i | 0.93 | 2.53 | 3.45 (4) | 175 |
C10—H10···N3ii | 0.93 | 2.51 | 3.405 (6) | 160 |
C13—H13···O2iii | 0.93 | 2.56 | 3.313 (6) | 139 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z. |