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In the title complex, [FeCl2(C16H10N3O3)(C3H7NO)], the FeIII ion is in an octahedral environment, with the equatorial plane being defined by the two N and one O atoms of the tridentate ligand 2-hydroxy-5-nitro-N-(8-quinolyl)­salicyl­ald­imine, and a chlorine, the octahedron being completed by the other chlorine and a di­methyl­form­amide (DMF) O atom in axial positions. Non-classical hydrogen bonds between 8-amino­quinolyl C-H groups and nitro O and Cl atoms of neighbouring mol­ecules generate a layered hydrogen-bonded network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010073/ob6137sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010073/ob6137Isup2.hkl
Contains datablock I

CCDC reference: 189865

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.090
  • wR factor = 0.244
  • Data-to-parameter ratio = 16.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.05 From the CIF: _reflns_number_total 4582 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4959 Completeness (_total/calc) 92.40% Alert C: < 95% complete RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.111 PLAT_213 Alert C Atom O2 has ADP max/min Ratio ........... 3.50 prolate
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Dichloro(dimethylformamide)[2-hydroxy-5-nitro-N-(8- quinolyl)salicylaldiminato]iron(III) top
Crystal data top
[FeCl2(C16H10N3O3)(C3H7NO)]Z = 2
Mr = 492.12F(000) = 502
Triclinic, P1Dx = 1.597 Mg m3
a = 9.205 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.372 (2) ÅCell parameters from 742 reflections
c = 10.989 (2) Åθ = 5.1–46.3°
α = 81.831 (4)°µ = 1.03 mm1
β = 87.033 (4)°T = 293 K
γ = 80.405 (4)°Needle, black
V = 1023.6 (4) Å30.20 × 0.10 × 0.10 mm
Data collection top
Bruker CCD area-detector
diffractometer
4582 independent reflections
Radiation source: sealed tube2740 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.111
φ and ω scansθmax = 28.1°, θmin = 2.2°
Absorption correction: part of the refinement model (ΔF)
(Sheldrick, 1990)
h = 1212
Tmin = 0.816, Tmax = 0.908k = 713
6454 measured reflectionsl = 1413
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)] = 0.090Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.244H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.1404P)2]
where P = (Fo2 + 2Fc2)/3
4582 reflections(Δ/σ)max < 0.001
273 parametersΔρmax = 0.64 e Å3
0 restraintsΔρmin = 0.66 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*/Ueq
Fe10.57360 (8)0.71958 (7)0.73631 (7)0.0342 (3)
Cl10.77623 (16)0.75476 (16)0.61037 (14)0.0499 (4)
Cl20.68525 (17)0.53101 (14)0.85062 (15)0.0490 (4)
O40.3766 (4)0.7111 (4)0.8508 (4)0.0439 (10)
O30.4723 (4)0.6449 (4)0.6211 (4)0.0428 (10)
N20.4507 (5)0.9089 (4)0.6641 (4)0.0344 (10)
C130.1221 (7)0.7718 (7)0.3997 (6)0.0480 (15)
C50.5810 (6)0.9818 (5)0.8167 (5)0.0361 (12)
C110.2958 (6)0.8242 (5)0.5335 (5)0.0340 (11)
C150.2968 (7)0.5980 (6)0.4971 (5)0.0453 (14)
H150.33550.50870.51220.054*
N40.1713 (6)0.6252 (5)0.8368 (5)0.0495 (13)
N10.6258 (5)0.8518 (4)0.8551 (4)0.0358 (10)
C80.4849 (8)1.2445 (6)0.7335 (6)0.0516 (16)
H80.45341.33290.70430.062*
C70.4398 (7)1.1472 (5)0.6742 (6)0.0431 (13)
H70.37871.17120.60710.052*
C60.4859 (6)1.0178 (5)0.7153 (5)0.0353 (12)
C10.7093 (6)0.8168 (6)0.9525 (5)0.0449 (14)
H10.74010.72750.97810.054*
C40.6223 (6)1.0810 (6)0.8773 (5)0.0421 (13)
C160.3585 (6)0.6896 (6)0.5533 (5)0.0392 (13)
C170.3116 (7)0.6181 (6)0.8461 (6)0.0456 (14)
H170.36860.53480.84960.055*
N30.0025 (7)0.8160 (6)0.3145 (6)0.0696 (19)
C100.3450 (6)0.9249 (5)0.5877 (5)0.0369 (12)
H100.29651.01070.56620.044*
C120.1772 (7)0.8628 (6)0.4534 (6)0.0454 (14)
H120.13620.95150.43710.055*
C140.1800 (7)0.6393 (6)0.4203 (6)0.0498 (16)
H140.14050.57860.38260.060*
C30.7123 (7)1.0378 (7)0.9811 (6)0.0524 (16)
H30.74331.09921.02360.063*
C20.7526 (7)0.9078 (7)1.0179 (6)0.0518 (16)
H20.80950.87931.08710.062*
C90.5736 (7)1.2133 (6)0.8327 (6)0.0492 (15)
H90.60141.27980.87040.059*
O20.0450 (8)0.7356 (6)0.2654 (7)0.126 (3)
O10.0491 (7)0.9327 (6)0.2966 (6)0.091 (2)
C190.1011 (9)0.5110 (8)0.8294 (8)0.077 (2)
H19A0.17530.43470.82540.116*
H19B0.04320.52670.75710.116*
H19C0.03850.49630.90100.116*
C180.0766 (9)0.7517 (10)0.8343 (11)0.099 (3)
H18A0.05070.76860.91700.149*
H18B0.01130.75060.79130.149*
H18C0.12740.81980.79300.149*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0365 (4)0.0291 (5)0.0368 (5)0.0004 (3)0.0121 (3)0.0054 (3)
Cl10.0451 (8)0.0567 (10)0.0443 (8)0.0019 (7)0.0040 (6)0.0010 (7)
Cl20.0544 (9)0.0335 (8)0.0558 (9)0.0010 (6)0.0183 (7)0.0045 (6)
O40.043 (2)0.038 (2)0.054 (2)0.0114 (18)0.0024 (18)0.0133 (19)
O30.039 (2)0.034 (2)0.057 (3)0.0066 (16)0.0242 (18)0.0165 (18)
N20.037 (2)0.030 (2)0.037 (2)0.0007 (18)0.0087 (18)0.0082 (19)
C130.046 (3)0.053 (4)0.045 (3)0.004 (3)0.021 (3)0.014 (3)
C50.035 (3)0.037 (3)0.036 (3)0.001 (2)0.005 (2)0.008 (2)
C110.038 (3)0.028 (3)0.035 (3)0.002 (2)0.008 (2)0.007 (2)
C150.051 (3)0.035 (3)0.049 (3)0.006 (3)0.013 (3)0.016 (3)
N40.044 (3)0.049 (3)0.060 (3)0.014 (2)0.009 (2)0.010 (2)
N10.045 (3)0.031 (2)0.032 (2)0.006 (2)0.0117 (19)0.0037 (19)
C80.080 (5)0.023 (3)0.051 (4)0.007 (3)0.004 (3)0.005 (3)
C70.056 (3)0.029 (3)0.046 (3)0.006 (3)0.011 (3)0.006 (2)
C60.038 (3)0.035 (3)0.034 (3)0.009 (2)0.003 (2)0.007 (2)
C10.046 (3)0.046 (4)0.043 (3)0.002 (3)0.015 (3)0.009 (3)
C40.045 (3)0.037 (3)0.046 (3)0.005 (3)0.003 (3)0.015 (3)
C160.045 (3)0.044 (3)0.031 (3)0.003 (3)0.009 (2)0.012 (2)
C170.050 (3)0.039 (3)0.047 (3)0.003 (3)0.007 (3)0.005 (3)
N30.078 (4)0.052 (4)0.080 (4)0.007 (3)0.049 (4)0.018 (3)
C100.049 (3)0.021 (3)0.037 (3)0.003 (2)0.012 (2)0.001 (2)
C120.048 (3)0.036 (3)0.052 (4)0.003 (3)0.017 (3)0.010 (3)
C140.049 (3)0.042 (4)0.063 (4)0.003 (3)0.025 (3)0.020 (3)
C30.047 (3)0.067 (5)0.051 (4)0.010 (3)0.010 (3)0.031 (3)
C20.049 (3)0.063 (4)0.044 (3)0.000 (3)0.016 (3)0.013 (3)
C90.063 (4)0.038 (3)0.053 (4)0.016 (3)0.006 (3)0.017 (3)
O20.146 (6)0.069 (4)0.175 (7)0.012 (4)0.131 (6)0.044 (4)
O10.094 (4)0.069 (4)0.111 (5)0.013 (3)0.071 (4)0.020 (3)
C190.069 (5)0.069 (5)0.103 (7)0.035 (4)0.013 (4)0.010 (5)
C180.054 (5)0.093 (7)0.157 (10)0.001 (5)0.026 (5)0.044 (7)
Geometric parameters (Å, º) top
Fe1—O31.927 (4)C8—C91.365 (9)
Fe1—N12.147 (4)C8—C71.404 (8)
Fe1—O42.160 (4)C8—H80.9300
Fe1—N22.162 (4)C7—C61.358 (8)
Fe1—Cl22.2858 (16)C7—H70.9300
Fe1—Cl12.3116 (18)C1—C21.383 (8)
O4—C171.226 (7)C1—H10.9300
O3—C161.299 (6)C4—C91.397 (8)
N2—C101.293 (7)C4—C31.420 (8)
N2—C61.420 (7)C17—H170.9300
C13—C121.359 (8)N3—O21.205 (7)
C13—C141.380 (9)N3—O11.217 (7)
C13—N31.455 (7)C10—H100.9300
C5—N11.355 (7)C12—H120.9300
C5—C41.414 (8)C14—H140.9300
C5—C61.422 (7)C3—C21.346 (9)
C11—C121.406 (7)C3—H30.9300
C11—C161.410 (8)C2—H20.9300
C11—C101.419 (7)C9—H90.9300
C15—C141.374 (8)C19—H19A0.9600
C15—C161.410 (8)C19—H19B0.9600
C15—H150.9300C19—H19C0.9600
N4—C171.289 (8)C18—H18A0.9600
N4—C181.447 (10)C18—H18B0.9600
N4—C191.454 (8)C18—H18C0.9600
N1—C11.323 (7)
O3—Fe1—N1161.49 (16)N2—C6—C5114.1 (5)
O3—Fe1—O485.20 (17)N1—C1—C2122.6 (6)
N1—Fe1—O485.47 (16)N1—C1—H1118.7
O3—Fe1—N286.91 (16)C2—C1—H1118.7
N1—Fe1—N275.96 (16)C9—C4—C5119.0 (5)
O4—Fe1—N281.82 (17)C9—C4—C3124.2 (6)
O3—Fe1—Cl2100.15 (12)C5—C4—C3116.8 (6)
N1—Fe1—Cl295.70 (12)O3—C16—C15117.7 (5)
O4—Fe1—Cl289.43 (12)O3—C16—C11123.0 (5)
N2—Fe1—Cl2168.29 (13)C15—C16—C11119.3 (5)
O3—Fe1—Cl196.91 (14)O4—C17—N4125.9 (6)
N1—Fe1—Cl190.74 (13)O4—C17—H17117.0
O4—Fe1—Cl1173.40 (11)N4—C17—H17117.0
N2—Fe1—Cl192.03 (13)O2—N3—O1121.7 (6)
Cl2—Fe1—Cl196.34 (6)O2—N3—C13119.1 (6)
C17—O4—Fe1117.0 (4)O1—N3—C13119.2 (6)
C16—O3—Fe1133.6 (4)N2—C10—C11126.3 (5)
C10—N2—C6120.7 (5)N2—C10—H10116.9
C10—N2—Fe1124.4 (4)C11—C10—H10116.9
C6—N2—Fe1114.7 (3)C13—C12—C11120.6 (5)
C12—C13—C14121.9 (5)C13—C12—H12119.7
C12—C13—N3119.0 (6)C11—C12—H12119.7
C14—C13—N3119.1 (5)C15—C14—C13119.2 (5)
N1—C5—C4121.7 (5)C15—C14—H14120.4
N1—C5—C6118.5 (5)C13—C14—H14120.4
C4—C5—C6119.8 (5)C2—C3—C4119.9 (6)
C12—C11—C16118.3 (5)C2—C3—H3120.0
C12—C11—C10117.2 (5)C4—C3—H3120.0
C16—C11—C10124.6 (5)C3—C2—C1119.8 (6)
C14—C15—C16120.7 (6)C3—C2—H2120.1
C14—C15—H15119.6C1—C2—H2120.1
C16—C15—H15119.6C8—C9—C4119.7 (5)
C17—N4—C18119.5 (6)C8—C9—H9120.1
C17—N4—C19123.2 (6)C4—C9—H9120.1
C18—N4—C19117.2 (6)N4—C19—H19A109.5
C1—N1—C5119.2 (5)N4—C19—H19B109.5
C1—N1—Fe1125.2 (4)H19A—C19—H19B109.5
C5—N1—Fe1115.3 (3)N4—C19—H19C109.5
C9—C8—C7122.0 (6)H19A—C19—H19C109.5
C9—C8—H8119.0H19B—C19—H19C109.5
C7—C8—H8119.0N4—C18—H18A109.5
C6—C7—C8119.6 (6)N4—C18—H18B109.5
C6—C7—H7120.2H18A—C18—H18B109.5
C8—C7—H7120.2N4—C18—H18C109.5
C7—C6—N2126.0 (5)H18A—C18—H18C109.5
C7—C6—C5119.9 (5)H18B—C18—H18C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···Cl20.932.763.359 (6)123
C2—H2···O2i0.932.583.478 (10)164
C7—H7···Cl1ii0.932.793.719 (7)174
C9—H9···Cl2iii0.932.813.645 (6)149
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+2, z+1; (iii) x, y+1, z.
 

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