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The title compound, 1,2-bis(4-nitro­phenyl)­ferrocene, [Fe(C5H5)(C17H11N2O4)], crystallizes with the planes of the two vicinal 4-nitro­phenyl rings subtending angles of 46.04 (6) and 36.30 (7)° at the plane of the substituted cyclo­penta­diene ring of the ferrocene moiety.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301599X/tk6123sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680301599X/tk6123Isup2.hkl
Contains datablock I

CCDC reference: 221663

Key indicators

  • Single-crystal X-ray study
  • T = 164 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.027
  • wR factor = 0.076
  • Data-to-parameter ratio = 13.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990) and TITAN2000 (Hunter & Simpson, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) and TITAN2000; molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

η5-bis(1,2-(4-nitrophenyl)cyclopentadiene- η5cyclopentadieneiron top
Crystal data top
[Fe(C5H5)(C17H11N2O4)]F(000) = 880
Mr = 428.22Dx = 1.594 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5205 reflections
a = 7.4359 (10) Åθ = 5.5–52.7°
b = 14.0883 (19) ŵ = 0.88 mm1
c = 17.042 (2) ÅT = 164 K
β = 92.048 (2)°Block, red
V = 1784.1 (4) Å30.45 × 0.23 × 0.10 mm
Z = 4
Data collection top
Bruker CCD area-detector
diffractometer
3620 independent reflections
Radiation source: fine-focus sealed tube2945 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker 1999)
h = 99
Tmin = 0.776, Tmax = 0.916k = 1717
22614 measured reflectionsl = 1021
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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0488P)2]
where P = (Fo2 + 2Fc2)/3
3620 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.41 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
C10.4335 (2)0.61140 (11)0.11548 (9)0.0203 (4)
C110.3046 (2)0.61150 (12)0.04756 (9)0.0199 (4)
C120.2087 (2)0.69284 (12)0.02524 (9)0.0228 (4)
H120.22560.74970.05460.027*
C130.0898 (2)0.69198 (12)0.03879 (10)0.0241 (4)
H130.02160.74680.05270.029*
C140.0724 (2)0.60934 (13)0.08220 (9)0.0231 (4)
N10.0486 (2)0.60899 (12)0.15174 (9)0.0306 (4)
O110.1644 (2)0.67122 (10)0.15756 (8)0.0412 (4)
O120.03000 (19)0.54680 (11)0.20063 (8)0.0421 (4)
C150.1647 (2)0.52739 (13)0.06238 (10)0.0251 (4)
H150.15050.47160.09330.030*
C160.2782 (2)0.52856 (12)0.00346 (10)0.0232 (4)
H160.33940.47210.01910.028*
C20.5686 (2)0.68198 (12)0.13565 (10)0.0209 (4)
C210.6204 (2)0.76687 (12)0.09203 (9)0.0216 (4)
C220.6805 (3)0.84768 (13)0.13219 (11)0.0317 (4)
H220.68310.84810.18800.038*
C230.7364 (3)0.92721 (13)0.09227 (11)0.0341 (5)
H230.77770.98200.12000.041*
C240.7310 (2)0.92532 (13)0.01108 (11)0.0275 (4)
N20.7887 (2)1.00957 (12)0.03156 (10)0.0372 (4)
O210.8395 (2)1.07874 (10)0.00612 (9)0.0492 (4)
O220.7887 (3)1.00617 (12)0.10301 (9)0.0706 (6)
C250.6758 (2)0.84634 (13)0.03053 (11)0.0286 (4)
H250.67560.84600.08630.034*
C260.6207 (2)0.76748 (13)0.01027 (10)0.0255 (4)
H260.58230.71250.01800.031*
C30.6575 (2)0.65109 (12)0.20729 (10)0.0244 (4)
H30.75230.68370.23470.029*
C40.5812 (2)0.56454 (13)0.23032 (10)0.0269 (4)
H40.61570.52890.27580.032*
C50.4445 (2)0.53957 (12)0.17433 (10)0.0241 (4)
H50.37210.48410.17570.029*
Fe10.39000 (3)0.669262 (17)0.222860 (13)0.02021 (9)
C60.1356 (2)0.72481 (14)0.22060 (10)0.0314 (4)
H60.05010.72150.17790.038*
C70.2635 (3)0.79705 (14)0.23300 (12)0.0358 (5)
H70.27930.85090.20040.043*
C80.3645 (3)0.77553 (14)0.30257 (11)0.0353 (5)
H80.46050.81210.32510.042*
C90.2966 (3)0.68933 (14)0.33267 (11)0.0305 (4)
H90.33930.65810.37910.037*
C100.1549 (2)0.65790 (13)0.28183 (10)0.0288 (4)
H100.08530.60200.28780.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0197 (8)0.0190 (8)0.0222 (8)0.0014 (7)0.0031 (7)0.0022 (7)
C110.0177 (8)0.0224 (9)0.0199 (8)0.0032 (7)0.0034 (6)0.0004 (7)
C120.0246 (9)0.0220 (9)0.0219 (9)0.0019 (7)0.0012 (7)0.0029 (7)
C130.0214 (9)0.0254 (9)0.0254 (9)0.0001 (7)0.0005 (7)0.0030 (7)
C140.0200 (8)0.0310 (10)0.0181 (8)0.0064 (7)0.0005 (7)0.0004 (7)
N10.0261 (8)0.0395 (10)0.0260 (8)0.0112 (7)0.0018 (6)0.0023 (7)
O110.0366 (8)0.0491 (9)0.0368 (8)0.0032 (7)0.0133 (6)0.0031 (6)
O120.0459 (9)0.0490 (9)0.0310 (8)0.0100 (7)0.0063 (7)0.0137 (7)
C150.0240 (9)0.0255 (9)0.0262 (9)0.0051 (7)0.0042 (7)0.0071 (7)
C160.0200 (9)0.0207 (9)0.0291 (9)0.0004 (7)0.0015 (7)0.0009 (7)
C20.0185 (8)0.0239 (9)0.0205 (8)0.0006 (7)0.0027 (7)0.0022 (7)
C210.0163 (8)0.0244 (9)0.0242 (9)0.0006 (7)0.0014 (7)0.0008 (7)
C220.0403 (11)0.0327 (11)0.0222 (9)0.0093 (8)0.0032 (8)0.0040 (7)
C230.0427 (12)0.0264 (10)0.0332 (11)0.0112 (9)0.0013 (9)0.0044 (8)
C240.0246 (9)0.0262 (9)0.0317 (10)0.0038 (7)0.0002 (7)0.0061 (8)
N20.0352 (10)0.0349 (10)0.0410 (10)0.0069 (8)0.0045 (8)0.0108 (8)
O210.0660 (11)0.0247 (7)0.0578 (10)0.0103 (7)0.0170 (8)0.0012 (7)
O220.1019 (15)0.0702 (12)0.0377 (10)0.0465 (11)0.0229 (9)0.0272 (8)
C250.0285 (10)0.0360 (11)0.0212 (9)0.0052 (8)0.0011 (8)0.0032 (7)
C260.0255 (9)0.0275 (9)0.0233 (9)0.0048 (7)0.0002 (7)0.0027 (7)
C30.0176 (8)0.0314 (10)0.0240 (9)0.0002 (7)0.0006 (7)0.0015 (7)
C40.0257 (9)0.0296 (10)0.0252 (9)0.0068 (8)0.0004 (7)0.0033 (8)
C50.0245 (9)0.0202 (9)0.0276 (9)0.0021 (7)0.0017 (7)0.0012 (7)
Fe10.01979 (14)0.02129 (14)0.01963 (14)0.00012 (10)0.00195 (9)0.00042 (10)
C60.0230 (9)0.0429 (12)0.0285 (10)0.0106 (8)0.0053 (8)0.0014 (8)
C70.0429 (12)0.0253 (9)0.0404 (11)0.0096 (9)0.0193 (10)0.0043 (9)
C80.0382 (11)0.0334 (11)0.0352 (11)0.0061 (9)0.0116 (9)0.0135 (9)
C90.0319 (10)0.0386 (11)0.0212 (9)0.0004 (8)0.0060 (8)0.0014 (8)
C100.0249 (9)0.0333 (11)0.0288 (10)0.0020 (7)0.0091 (8)0.0008 (8)
Geometric parameters (Å, º) top
C1—C21.446 (2)C21—C221.394 (2)
C1—C111.476 (2)C22—C231.382 (3)
C1—C51.425 (2)C22—H220.9500
C2—C31.435 (2)C23—C241.383 (3)
C2—C211.467 (2)C23—H230.9500
C3—C41.407 (2)C24—C251.374 (3)
C4—C51.413 (2)C24—N21.464 (2)
C6—C71.404 (3)N2—O221.218 (2)
C6—C101.410 (3)N2—O211.220 (2)
C7—C81.414 (3)C25—C261.381 (2)
C8—C91.418 (3)C25—H250.9500
C9—C101.412 (3)C26—H260.9500
C1—Fe12.0396 (16)C3—Fe12.0325 (17)
C11—C121.395 (2)C3—H30.9500
C11—C161.399 (2)C4—Fe12.0497 (17)
C12—C131.380 (2)C4—H40.9500
C12—H120.9500C5—Fe12.0521 (17)
C13—C141.383 (2)C5—H50.9500
C13—H130.9500Fe1—C82.0349 (18)
C14—C151.379 (2)Fe1—C92.0387 (18)
C14—N11.462 (2)Fe1—C72.0414 (19)
N1—O121.220 (2)Fe1—C62.0460 (18)
N1—O111.230 (2)Fe1—C102.0538 (18)
C15—C161.380 (2)C6—H60.9500
C15—H150.9500C7—H70.9500
C16—H160.9500C8—H80.9500
C2—Fe12.0363 (17)C9—H90.9500
C21—C261.393 (2)C10—H100.9500
C2—C1—C11127.72 (14)C8—Fe1—C2120.08 (7)
C5—C1—C11124.88 (15)C3—Fe1—C9120.28 (7)
C1—C2—C21129.25 (15)C8—Fe1—C940.75 (7)
C3—C2—C21123.87 (15)C2—Fe1—C9155.52 (7)
C5—C1—C2107.40 (14)C3—Fe1—C169.21 (7)
C5—C1—Fe170.09 (9)C8—Fe1—C1156.13 (7)
C2—C1—Fe169.09 (9)C2—Fe1—C141.56 (6)
C11—C1—Fe1125.72 (11)C9—Fe1—C1161.63 (7)
C12—C11—C16118.59 (15)C3—Fe1—C7125.33 (8)
C12—C11—C1121.71 (15)C8—Fe1—C740.58 (8)
C16—C11—C1119.70 (15)C2—Fe1—C7107.38 (7)
C13—C12—C11121.01 (16)C9—Fe1—C768.10 (8)
C13—C12—H12119.5C1—Fe1—C7121.11 (7)
C11—C12—H12119.5C3—Fe1—C6162.59 (7)
C12—C13—C14118.40 (16)C8—Fe1—C667.86 (8)
C12—C13—H13120.8C2—Fe1—C6125.40 (7)
C14—C13—H13120.8C9—Fe1—C667.63 (8)
C15—C14—C13122.51 (16)C1—Fe1—C6108.19 (7)
C15—C14—N1118.83 (15)C7—Fe1—C640.17 (8)
C13—C14—N1118.66 (16)C3—Fe1—C440.31 (7)
O12—N1—O11123.57 (16)C8—Fe1—C4124.68 (8)
O12—N1—C14118.30 (16)C2—Fe1—C468.87 (7)
O11—N1—C14118.13 (15)C9—Fe1—C4107.52 (7)
C14—C15—C16118.28 (16)C1—Fe1—C468.66 (7)
C14—C15—H15120.9C7—Fe1—C4161.85 (8)
C16—C15—H15120.9C6—Fe1—C4156.23 (8)
C15—C16—C11121.13 (16)C3—Fe1—C568.08 (7)
C15—C16—H16119.4C8—Fe1—C5161.54 (8)
C11—C16—H16119.4C2—Fe1—C568.94 (7)
C3—C2—C1106.78 (14)C9—Fe1—C5124.90 (7)
C3—C2—Fe169.21 (9)C1—Fe1—C540.76 (6)
C1—C2—Fe169.34 (9)C7—Fe1—C5156.58 (8)
C21—C2—Fe1129.15 (12)C6—Fe1—C5121.93 (8)
C26—C21—C22118.29 (16)C4—Fe1—C540.31 (7)
C26—C21—C2121.44 (15)C3—Fe1—C10155.28 (7)
C22—C21—C2120.17 (15)C8—Fe1—C1068.26 (8)
C23—C22—C21121.15 (17)C2—Fe1—C10162.35 (7)
C23—C22—H22119.4C9—Fe1—C1040.35 (7)
C21—C22—H22119.4C1—Fe1—C10124.96 (7)
C22—C23—C24118.56 (17)C7—Fe1—C1067.94 (8)
C22—C23—H23120.7C6—Fe1—C1040.22 (7)
C24—C23—H23120.7C4—Fe1—C10120.95 (7)
C25—C24—C23121.96 (17)C5—Fe1—C10108.17 (7)
C25—C24—N2119.19 (16)C7—C6—C10108.86 (17)
C23—C24—N2118.84 (17)C7—C6—Fe169.74 (11)
O22—N2—O21123.12 (17)C10—C6—Fe170.18 (10)
O22—N2—C24118.34 (17)C7—C6—H6125.6
O21—N2—C24118.50 (16)C10—C6—H6125.6
C24—C25—C26118.70 (17)Fe1—C6—H6126.1
C24—C25—H25120.7C6—C7—C8107.91 (17)
C26—C25—H25120.7C6—C7—Fe170.09 (11)
C25—C26—C21121.31 (16)C8—C7—Fe169.46 (11)
C25—C26—H26119.3C6—C7—H7126.0
C21—C26—H26119.3C8—C7—H7126.0
C4—C3—C2108.78 (15)Fe1—C7—H7126.0
C4—C3—Fe170.50 (10)C7—C8—C9107.55 (18)
C2—C3—Fe169.49 (9)C7—C8—Fe169.95 (10)
C4—C3—H3125.6C9—C8—Fe169.77 (10)
C2—C3—H3125.6C7—C8—H8126.2
Fe1—C3—H3126.0C9—C8—H8126.2
C3—C4—C5108.36 (15)Fe1—C8—H8125.6
C3—C4—Fe169.19 (10)C10—C9—C8108.33 (17)
C5—C4—Fe169.93 (10)C10—C9—Fe170.40 (10)
C3—C4—H4125.8C8—C9—Fe169.48 (10)
C5—C4—H4125.8C10—C9—H9125.8
Fe1—C4—H4126.6C8—C9—H9125.8
C4—C5—C1108.67 (15)Fe1—C9—H9125.9
C4—C5—Fe169.76 (10)C6—C10—C9107.35 (17)
C1—C5—Fe169.15 (9)C6—C10—Fe169.59 (10)
C4—C5—H5125.7C9—C10—Fe169.25 (10)
C1—C5—H5125.7C6—C10—H10126.3
Fe1—C5—H5127.0C9—C10—H10126.3
C3—Fe1—C8107.14 (8)Fe1—C10—H10126.4
C3—Fe1—C241.30 (7)
 

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