Download citation
Download citation
link to html
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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013005/na6332sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013005/na6332Isup2.hkl
Contains datablock I

CCDC reference: 245111

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Computing details top

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 = 378.20Dx = 1.497 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.7388 (8) ÅCell parameters from 3662 reflections
b = 13.7957 (13) Åθ = 4–27°
c = 14.4499 (14) ŵ = 0.92 mm1
β = 105.620 (2)°T = 298 K
V = 1677.7 (3) Å3Block, black
Z = 40.18 × 0.18 × 0.10 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3528 independent reflections
Radiation source: fine-focus sealed tube2159 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
φ and ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 511
Tmin = 0.852, Tmax = 0.914k = 1717
9418 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.225H-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 parametersΔρmax = 0.86 e Å3
0 restraintsΔρmin = 0.40 e Å3
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
xyzUiso*/UeqOcc. (<1)
Fe10.14566 (9)0.99429 (4)0.10846 (5)0.0514 (3)
C10.0778 (6)0.8059 (3)0.1059 (3)0.0533 (12)
C20.0094 (6)0.8133 (3)0.0353 (4)0.0496 (12)
C30.0271 (7)0.7310 (4)0.0147 (4)0.0585 (13)
H30.08100.73540.06190.070*
C40.0314 (8)0.6424 (4)0.0028 (4)0.0741 (17)
H40.01620.58800.03170.089*
C50.1118 (9)0.6342 (4)0.0727 (5)0.087 (2)
H50.14940.57420.08600.104*
C60.1375 (8)0.7162 (4)0.1224 (4)0.0731 (17)
H60.19500.71080.16770.088*
C70.1111 (7)0.8893 (4)0.1572 (4)0.0590 (13)
H70.19110.88430.18830.071*
C80.0902 (8)1.0568 (4)0.2064 (5)0.0744 (17)
H8A0.14711.03740.25250.089*
H8B0.15911.09770.15810.089*
C90.0630 (11)1.1096 (5)0.2571 (4)0.092 (2)
H90.03521.17680.26720.111*
C100.2561 (7)1.1846 (4)0.1883 (3)0.0584 (14)
H100.25411.23570.22990.070*
C110.3598 (7)1.1937 (3)0.1264 (3)0.0541 (13)
C120.3777 (6)1.1210 (3)0.0605 (3)0.0480 (11)
C130.4835 (6)1.1369 (4)0.0050 (4)0.0588 (14)
H130.49751.08930.03750.071*
C140.5665 (8)1.2214 (4)0.0122 (5)0.0754 (17)
H140.63731.22950.02510.091*
C150.5483 (9)1.2953 (5)0.0725 (5)0.091 (2)
H150.60501.35290.07590.109*
C160.4444 (8)1.2807 (4)0.1277 (4)0.0759 (18)
H160.42951.33050.16780.091*
C170.1371 (15)1.0701 (7)0.3470 (7)0.149 (4)
H17A0.17711.00690.33830.223*
H17B0.06081.06480.38370.223*
H17C0.22341.11080.38060.223*
N10.0374 (6)0.9706 (3)0.1623 (3)0.0550 (11)
N20.1674 (6)1.1111 (3)0.1908 (3)0.0583 (12)
N30.2972 (7)0.9007 (3)0.2108 (3)0.0670 (13)
N40.4371 (8)0.8997 (4)0.2381 (3)0.0662 (13)
N50.570 (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)
O10.0632 (4)0.8979 (2)0.0133 (2)0.0487 (8)
O20.2979 (4)1.0389 (2)0.0498 (2)0.0521 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0631 (6)0.0411 (4)0.0548 (5)0.0008 (3)0.0239 (4)0.0022 (3)
C10.049 (3)0.054 (3)0.056 (3)0.001 (2)0.012 (3)0.012 (2)
C20.048 (3)0.044 (3)0.054 (3)0.003 (2)0.008 (2)0.008 (2)
C30.052 (3)0.044 (3)0.077 (3)0.001 (2)0.014 (3)0.004 (2)
C40.079 (5)0.044 (3)0.096 (4)0.002 (3)0.019 (4)0.012 (3)
C50.090 (5)0.048 (3)0.114 (5)0.012 (3)0.014 (4)0.019 (3)
C60.073 (4)0.075 (4)0.072 (4)0.014 (3)0.020 (3)0.023 (3)
C70.060 (4)0.064 (3)0.055 (3)0.001 (3)0.019 (3)0.012 (2)
C80.083 (5)0.066 (3)0.089 (4)0.004 (3)0.048 (4)0.014 (3)
C90.161 (8)0.077 (4)0.059 (4)0.014 (5)0.063 (5)0.003 (3)
C100.072 (4)0.051 (3)0.049 (3)0.006 (3)0.011 (3)0.009 (2)
C110.055 (3)0.045 (3)0.054 (3)0.003 (2)0.001 (3)0.007 (2)
C120.047 (3)0.038 (2)0.054 (3)0.003 (2)0.005 (2)0.0023 (19)
C130.052 (3)0.049 (3)0.080 (4)0.001 (2)0.027 (3)0.000 (2)
C140.066 (4)0.069 (4)0.097 (4)0.008 (3)0.030 (4)0.005 (3)
C150.093 (5)0.063 (4)0.112 (5)0.037 (4)0.019 (5)0.008 (4)
C160.089 (5)0.048 (3)0.083 (4)0.018 (3)0.010 (4)0.018 (3)
C170.162 (11)0.142 (8)0.142 (8)0.012 (8)0.040 (8)0.036 (7)
N10.063 (3)0.057 (2)0.053 (2)0.007 (2)0.029 (2)0.0046 (19)
N20.081 (3)0.043 (2)0.053 (2)0.002 (2)0.023 (2)0.0063 (17)
N30.063 (3)0.055 (3)0.082 (3)0.007 (3)0.018 (3)0.017 (2)
N40.079 (4)0.065 (3)0.060 (3)0.006 (3)0.027 (3)0.008 (2)
N50.051 (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)
O10.059 (2)0.0396 (16)0.0532 (18)0.0070 (16)0.0240 (17)0.0032 (13)
O20.062 (2)0.0376 (16)0.065 (2)0.0040 (16)0.0300 (18)0.0082 (14)
Geometric parameters (Å, º) top
Fe1—O21.864 (3)C9—C171.396 (11)
Fe1—O11.909 (3)C9—N21.490 (7)
Fe1—N21.981 (4)C9—H90.9800
Fe1—N11.985 (4)C10—N21.283 (7)
Fe1—N32.134 (5)C10—C111.439 (7)
C1—C61.388 (7)C10—H100.9301
C1—C21.431 (7)C11—C161.408 (7)
C1—C71.440 (7)C11—C121.422 (6)
C2—O11.329 (5)C12—O21.316 (5)
C2—C31.377 (7)C12—C131.394 (7)
C3—C41.375 (7)C13—C141.363 (8)
C3—H30.9301C13—H130.9301
C4—C51.381 (9)C14—C151.378 (9)
C4—H40.9301C14—H140.9299
C5—C61.390 (9)C15—C161.376 (9)
C5—H50.9300C15—H150.9299
C6—H60.9300C16—H160.9300
C7—N11.285 (6)C17—H17A0.9601
C7—H70.9300C17—H17B0.9601
C8—N11.482 (7)C17—H17C0.9600
C8—C91.527 (10)N3—N41.179 (7)
C8—H8A0.9700N4—N51.16 (4)
C8—H8B0.9700N4—N5'1.19 (4)
O2—Fe1—O194.59 (13)N2—C9—H9107.6
O2—Fe1—N292.26 (16)C8—C9—H9107.6
O1—Fe1—N2162.84 (18)N2—C10—C11125.0 (4)
O2—Fe1—N1169.01 (15)N2—C10—H10117.6
O1—Fe1—N188.83 (16)C11—C10—H10117.4
N2—Fe1—N181.73 (19)C16—C11—C12117.3 (5)
O2—Fe1—N397.43 (18)C16—C11—C10118.9 (5)
O1—Fe1—N396.95 (17)C12—C11—C10123.8 (5)
N2—Fe1—N397.74 (19)O2—C12—C13118.8 (4)
N1—Fe1—N392.51 (19)O2—C12—C11122.3 (5)
C6—C1—C2118.8 (5)C13—C12—C11118.9 (4)
C6—C1—C7119.1 (5)C14—C13—C12120.9 (5)
C2—C1—C7122.0 (4)C14—C13—H13119.6
O1—C2—C3120.1 (4)C12—C13—H13119.5
O1—C2—C1121.6 (4)C13—C14—C15122.1 (6)
C3—C2—C1118.2 (5)C13—C14—H14118.8
C4—C3—C2122.5 (5)C15—C14—H14119.1
C4—C3—H3118.7C16—C15—C14117.7 (6)
C2—C3—H3118.9C16—C15—H15121.3
C3—C4—C5119.6 (6)C14—C15—H15121.0
C3—C4—H4120.3C15—C16—C11123.0 (6)
C5—C4—H4120.1C15—C16—H16118.6
C4—C5—C6119.7 (5)C11—C16—H16118.5
C4—C5—H5120.1C9—C17—H17A109.0
C6—C5—H5120.2C9—C17—H17B109.1
C5—C6—C1121.1 (6)H17A—C17—H17B109.5
C5—C6—H6119.4C9—C17—H17C110.3
C1—C6—H6119.5H17A—C17—H17C109.5
N1—C7—C1124.0 (5)H17B—C17—H17C109.5
N1—C7—H7117.9C7—N1—C8121.1 (5)
C1—C7—H7118.1C7—N1—Fe1124.5 (4)
N1—C8—C9104.8 (5)C8—N1—Fe1114.4 (4)
N1—C8—H8A110.6C10—N2—C9120.6 (5)
C9—C8—H8A110.3C10—N2—Fe1125.9 (4)
N1—C8—H8B111.2C9—N2—Fe1113.5 (4)
C9—C8—H8B111.2N4—N3—Fe1129.2 (4)
H8A—C8—H8B108.7N5—N4—N3167 (3)
C17—C9—N2113.1 (8)N5—N4—N5'27 (5)
C17—C9—C8112.8 (7)N3—N4—N5'166 (7)
N2—C9—C8107.9 (5)C2—O1—Fe1121.9 (3)
C17—C9—H9107.6C12—O2—Fe1130.7 (3)
C6—C1—C2—O1176.9 (5)O2—Fe1—N1—C840.3 (10)
C7—C1—C2—O10.4 (8)O1—Fe1—N1—C8148.6 (4)
C6—C1—C2—C31.4 (7)N2—Fe1—N1—C817.0 (4)
C7—C1—C2—C3175.9 (5)N3—Fe1—N1—C8114.5 (4)
O1—C2—C3—C4177.6 (5)C11—C10—N2—C9179.4 (5)
C1—C2—C3—C42.0 (8)C11—C10—N2—Fe11.9 (8)
C2—C3—C4—C50.2 (9)C17—C9—N2—C1090.2 (8)
C3—C4—C5—C62.2 (10)C8—C9—N2—C10144.3 (6)
C4—C5—C6—C12.8 (10)C17—C9—N2—Fe192.1 (7)
C2—C1—C6—C51.0 (9)C8—C9—N2—Fe133.4 (6)
C7—C1—C6—C5178.4 (6)O2—Fe1—N2—C103.1 (5)
C6—C1—C7—N1165.6 (5)O1—Fe1—N2—C10110.4 (6)
C2—C1—C7—N117.1 (8)N1—Fe1—N2—C10167.7 (5)
N1—C8—C9—C1781.5 (7)N3—Fe1—N2—C10100.9 (5)
N1—C8—C9—N244.2 (6)O2—Fe1—N2—C9179.3 (4)
N2—C10—C11—C16176.7 (5)O1—Fe1—N2—C967.2 (7)
N2—C10—C11—C120.7 (9)N1—Fe1—N2—C99.9 (4)
C16—C11—C12—O2176.5 (5)N3—Fe1—N2—C981.5 (4)
C10—C11—C12—O21.0 (8)O2—Fe1—N3—N418.4 (6)
C16—C11—C12—C133.6 (7)O1—Fe1—N3—N4114.0 (6)
C10—C11—C12—C13179.0 (5)N2—Fe1—N3—N474.9 (6)
O2—C12—C13—C14178.8 (5)N1—Fe1—N3—N4156.9 (6)
C11—C12—C13—C141.3 (8)Fe1—N3—N4—N576 (8)
C12—C13—C14—C151.2 (10)Fe1—N3—N4—N5'124 (7)
C13—C14—C15—C161.2 (11)C3—C2—O1—Fe1146.6 (4)
C14—C15—C16—C111.3 (10)C1—C2—O1—Fe137.9 (6)
C12—C11—C16—C153.7 (9)O2—Fe1—O1—C2145.7 (4)
C10—C11—C16—C15178.8 (6)N2—Fe1—O1—C2101.1 (6)
C1—C7—N1—C8172.7 (5)N1—Fe1—O1—C244.8 (4)
C1—C7—N1—Fe14.4 (7)N3—Fe1—O1—C247.6 (4)
C9—C8—N1—C7144.4 (5)C13—C12—O2—Fe1178.5 (3)
C9—C8—N1—Fe138.3 (5)C11—C12—O2—Fe11.6 (7)
O2—Fe1—N1—C7137.0 (7)O1—Fe1—O2—C12161.3 (4)
O1—Fe1—N1—C728.6 (4)N2—Fe1—O2—C123.0 (4)
N2—Fe1—N1—C7165.7 (5)N1—Fe1—O2—C1253.5 (10)
N3—Fe1—N1—C768.3 (5)N3—Fe1—O2—C12101.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···N5i0.932.533.45 (4)175
C10—H10···N3ii0.932.513.405 (6)160
C13—H13···O2iii0.932.563.313 (6)139
Symmetry codes: (i) x1, y, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y+2, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds