metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Di­nitro­sylbis[tris­­(4-fluoro­phen­yl)phosphane]iron chloro­form monosolvate

aDepartment of Chemistry and Biochemistry, University of Oklahoma, 101 Stephenson Parkway, Norman, OK 73019-5251, USA
*Correspondence e-mail: mwjones@ou.edu

(Received 22 December 2010; accepted 7 February 2011; online 12 February 2011)

The title compound, [Fe(NO)2(C18H12F3P)2]·CHCl3, belongs to the family of metal dinitrosyl compounds with the general formula Fe(NO)2(L)x, referred to collectively as `dinitrosyl iron compounds' (DNICs). Herein we report the structure of a dinitrosyl iron diphosphane complex, (Fe(NO)2L2, with L = P(C6H4-p-F)3. The structure includes one metal complex mol­ecule and one chloro­form solvent mol­ecule. The iron atom is tetra­hedrally coordinated with two phosphane ligands and with two NO groups with Fe—N—O angles of 178.1 (2) and 177.0 (2)°.

Related literature

The starting compound, Fe(NO)2(CO)2, was prepared using a published method described by Eisch & King (1965[Eisch, J. J. & King, R. B. (1965). Metal Nitrosyl Derivatives, in Organometallic Syntheses. New York: Academic Press.]). For the structures of some related dinitrosyl complexes, see: Li et al. (2003[Li, L., Reginato, N., Urschey, M., Stradiotto, M. & Liarakos, J. D. (2003). Can. J. Chem. 82, 468-475.]); Atkinson et al. (1996[Atkinson, F. L., Blackwell, H. E., Brown, N. C., Connelly, N. G., Crossley, J. G., Orpen, A. G., Rieger, A. L. & Rieger, P. H. (1996). J. Chem. Soc. Dalton Trans. pp. 3491-3502.]); Li Kam Wah et al. (1989[Li Kam Wah, H., Postel, M. & Pierrot, M. (1989). Inorg. Chim. Acta, 165, 215-220.]); Albano et al. (1974[Albano, V. G., Araneo, A., Bellon, P. L., Ciani, G. & Manassero, M. (1974). J. Organomet. Chem. 67, 413-422.]). For general information on metal nitrosyl chemistry, see: Richter-Addo & Legzdins (1992[Richter-Addo, G. B. & Legzdins, P. (1992). In Metal Nitrosyls. New York: Oxford University Press Inc.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(NO)2(C18H12F3P)2]·CHCl3

  • Mr = 867.73

  • Monoclinic, P 21 /c

  • a = 13.994 (5) Å

  • b = 15.746 (6) Å

  • c = 16.716 (6) Å

  • β = 97.651 (8)°

  • V = 3651 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.79 mm−1

  • T = 100 K

  • 0.44 × 0.22 × 0.04 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001[Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.]) Tmin = 0.721, Tmax = 0.972

  • 22634 measured reflections

  • 6325 independent reflections

  • 5006 reflections with I > 2σ(I)

  • Rint = 0.056

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.115

  • S = 1.02

  • 6325 reflections

  • 478 parameters

  • H-atom parameters constrained

  • Δρmax = 1.24 e Å−3

  • Δρmin = −0.46 e Å−3

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The molecular structure of the title compound is shown in Fig. 1. The structure includes one metal complex molecule and one chloroform solvent molecule. The metal complex molecule possesses a distorted tetrahedral geometry around the iron center. The iron is bound to two nitrosyl groups via the nitrogen atoms and to two phosphine ligands via the phorphorus atoms. The Fe(NO)2 moiety exhibits an attracto conformation where the bond angle O···Fe···O < N—Fe—N (Richter-Addo & Legzdins, 1992). The N—Fe—N bond angle is 127.02 (11)° and the interphosphine bond angle, P—Fe—P, is 108.27 (4)°. The Fe—N—O bond angles are 178.1 (2)° and 177.0 (2)°.

Related literature top

The starting compound, Fe(NO)2(CO)2, was prepared using a published method described by Eisch & King (1965). For the structures of some related dinitrosyl complexes, see: Li et al. (2003); Atkinson et al. (1996); Li Kam Wah et al. (1989); Albano et al. (1974). For general information on metal nitrosyl chemistry, see: Richter-Addo & Legzdins (1992).

Experimental top

A light yellow toluene solution (5 ml) of P(C6H4-p-F)3 (127 mg, 0.40 mmol) was charged with Fe(NO)2(CO)2 (21 µL, 0.19 mmol) (Eisch & King, 1965). The light red/orange solution was heated and stirred under nitrogen for 3.25 h after which time the infrared spectrum was consistent with the presence of the product and no trace of Fe(NO)2(CO)2 (νCO = 2090 cm-1 and 2040 cm-1) was observed. The reaction mixture was filtered through celite under N2 and the solvent was subsequently removed under vacuum. Isolated yield of the Fe(NO)2L2 compound: 23%. IR (toluene, cm-1): νNO = 1720 s and 1682 s; 31P{1H} NMR (CDCl3): δ 59.3 (s) referenced to 85% H3PO4. Suitable crystals for X-ray diffraction studies were grown by slow evaporation of a chloroform solution of the complex under nitrogen at ambient temperature.

Refinement top

H atoms were placed using known geometry with C—H (phenyl = 0.95 Å, methylene = 1.00 Å). Displacement parameters of phenyl H atoms were set to 1.2 times the isotropic equivalent for the bonded C.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Hydrogen atoms were omitted for clarity. The displacement ellipsoids were drawn at the 50% probability level.
Dinitrosylbis[tris(4-fluorophenyl)phosphane]iron chloroform monosolvate top
Crystal data top
[Fe(NO)2(C18H12F3P)2]·CHCl3F(000) = 1752
Mr = 867.73Dx = 1.579 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5630 reflections
a = 13.994 (5) Åθ = 2.4–25.7°
b = 15.746 (6) ŵ = 0.79 mm1
c = 16.716 (6) ÅT = 100 K
β = 97.651 (8)°Prism, red
V = 3651 (2) Å30.44 × 0.22 × 0.04 mm
Z = 4
Data collection top
Bruker APEX CCD
diffractometer
6325 independent reflections
Radiation source: fine-focus sealed tube5006 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1616
Tmin = 0.721, Tmax = 0.972k = 1818
22634 measured reflectionsl = 1919
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.074P)2]
where P = (Fo2 + 2Fc2)/3
6325 reflections(Δ/σ)max = 0.001
478 parametersΔρmax = 1.24 e Å3
0 restraintsΔρmin = 0.46 e Å3
Crystal data top
[Fe(NO)2(C18H12F3P)2]·CHCl3V = 3651 (2) Å3
Mr = 867.73Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.994 (5) ŵ = 0.79 mm1
b = 15.746 (6) ÅT = 100 K
c = 16.716 (6) Å0.44 × 0.22 × 0.04 mm
β = 97.651 (8)°
Data collection top
Bruker APEX CCD
diffractometer
6325 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
5006 reflections with I > 2σ(I)
Tmin = 0.721, Tmax = 0.972Rint = 0.056
22634 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.02Δρmax = 1.24 e Å3
6325 reflectionsΔρmin = 0.46 e Å3
478 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.37827 (3)0.78849 (2)0.33064 (2)0.01773 (13)
P10.47836 (5)0.73871 (4)0.24750 (4)0.01786 (18)
P20.22602 (5)0.76296 (4)0.27435 (4)0.01742 (18)
F10.64936 (13)0.98173 (11)0.03475 (10)0.0316 (4)
F20.83075 (13)0.62487 (11)0.45867 (11)0.0377 (5)
F30.34188 (16)0.44281 (11)0.04389 (11)0.0474 (6)
F40.08751 (14)0.94290 (11)0.03130 (9)0.0358 (5)
F50.11645 (14)0.40322 (10)0.20664 (11)0.0380 (5)
F60.03371 (12)0.88266 (11)0.50522 (10)0.0325 (4)
O10.39333 (16)0.96864 (13)0.34007 (12)0.0307 (5)
O20.41657 (17)0.67401 (13)0.46305 (13)0.0366 (6)
N10.38753 (17)0.89340 (15)0.33402 (13)0.0213 (5)
N20.39889 (17)0.72178 (14)0.40736 (14)0.0228 (5)
C10.5291 (2)0.81458 (17)0.18170 (16)0.0185 (6)
C20.4853 (2)0.89178 (16)0.16116 (16)0.0194 (6)
H20.42730.90630.18180.023*
C30.5248 (2)0.94872 (17)0.11063 (17)0.0223 (6)
H30.49431.00140.09610.027*
C40.6085 (2)0.92645 (18)0.08276 (16)0.0227 (6)
C50.6549 (2)0.85066 (18)0.10161 (17)0.0246 (7)
H50.71320.83730.08110.030*
C60.6146 (2)0.79450 (18)0.15110 (17)0.0236 (7)
H60.64530.74160.16450.028*
C70.5880 (2)0.69932 (17)0.30903 (16)0.0195 (6)
C80.6333 (2)0.75458 (18)0.36730 (17)0.0244 (7)
H80.60680.80940.37330.029*
C90.7164 (2)0.73055 (19)0.41664 (18)0.0273 (7)
H90.74890.76890.45490.033*
C100.7504 (2)0.64994 (19)0.40848 (17)0.0258 (7)
C110.7081 (2)0.59301 (18)0.35257 (18)0.0250 (7)
H110.73410.53770.34860.030*
C120.6262 (2)0.61843 (18)0.30184 (17)0.0227 (6)
H120.59620.58040.26210.027*
C130.4398 (2)0.64918 (17)0.18126 (16)0.0200 (6)
C140.4392 (2)0.65064 (19)0.09849 (17)0.0295 (7)
H140.46150.69960.07350.035*
C150.4061 (3)0.5809 (2)0.05134 (19)0.0380 (8)
H150.40560.58160.00550.046*
C160.3742 (2)0.51132 (18)0.08944 (19)0.0317 (8)
C170.3733 (2)0.50733 (17)0.17158 (17)0.0233 (6)
H170.35140.45790.19620.028*
C180.4053 (2)0.57763 (17)0.21709 (17)0.0218 (6)
H180.40370.57710.27370.026*
C190.1808 (2)0.82030 (16)0.18227 (16)0.0197 (6)
C200.0885 (2)0.85538 (18)0.16838 (17)0.0243 (7)
H200.04670.85070.20850.029*
C210.0571 (2)0.89696 (19)0.09674 (18)0.0291 (7)
H210.00560.92120.08740.035*
C220.1186 (2)0.90232 (18)0.03967 (16)0.0251 (7)
C230.2093 (2)0.86878 (18)0.04979 (17)0.0267 (7)
H230.25010.87380.00890.032*
C240.2401 (2)0.82711 (18)0.12187 (17)0.0233 (6)
H240.30280.80280.13020.028*
C250.19084 (19)0.65336 (17)0.25032 (16)0.0191 (6)
C260.1510 (2)0.62711 (17)0.17335 (16)0.0208 (6)
H260.14030.66750.13090.025*
C270.1267 (2)0.54248 (18)0.15809 (17)0.0253 (7)
H270.10070.52430.10550.030*
C280.1411 (2)0.48607 (18)0.22068 (18)0.0265 (7)
C290.1803 (2)0.50879 (18)0.29794 (18)0.0249 (7)
H290.18900.46800.34020.030*
C300.2062 (2)0.59248 (17)0.31186 (17)0.0206 (6)
H300.23500.60920.36420.025*
C310.1431 (2)0.79517 (17)0.34546 (16)0.0188 (6)
C320.0698 (2)0.74415 (18)0.36738 (17)0.0226 (6)
H320.06000.68900.34470.027*
C330.0109 (2)0.77292 (18)0.42185 (17)0.0234 (6)
H330.03880.73800.43740.028*
C340.0260 (2)0.85280 (19)0.45277 (17)0.0240 (7)
C350.0971 (2)0.90590 (18)0.43289 (17)0.0253 (7)
H350.10510.96130.45530.030*
C360.1564 (2)0.87624 (18)0.37938 (17)0.0237 (6)
H360.20690.91130.36540.028*
Cl1S0.22226 (6)0.10408 (5)0.38685 (5)0.0335 (2)
Cl2S0.13359 (6)0.23683 (5)0.28321 (6)0.0417 (2)
Cl3S0.08805 (6)0.06170 (5)0.24465 (5)0.0344 (2)
C1S0.1178 (2)0.13555 (19)0.32295 (19)0.0297 (7)
H1S0.06310.13830.35570.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0201 (2)0.0199 (2)0.0119 (2)0.00032 (16)0.00246 (16)0.00012 (15)
P10.0197 (4)0.0194 (4)0.0134 (4)0.0006 (3)0.0022 (3)0.0002 (3)
P20.0198 (4)0.0196 (4)0.0118 (4)0.0009 (3)0.0019 (3)0.0005 (3)
F10.0371 (11)0.0325 (9)0.0249 (10)0.0067 (8)0.0033 (8)0.0082 (8)
F20.0271 (10)0.0443 (11)0.0363 (11)0.0028 (8)0.0156 (8)0.0083 (9)
F30.0810 (16)0.0270 (10)0.0271 (10)0.0122 (9)0.0192 (10)0.0062 (8)
F40.0521 (12)0.0392 (10)0.0137 (9)0.0141 (9)0.0048 (8)0.0082 (7)
F50.0498 (12)0.0205 (9)0.0384 (11)0.0079 (8)0.0137 (9)0.0008 (8)
F60.0336 (11)0.0411 (11)0.0245 (10)0.0029 (8)0.0098 (8)0.0061 (8)
O10.0412 (14)0.0221 (11)0.0293 (12)0.0027 (10)0.0064 (10)0.0002 (9)
O20.0474 (15)0.0364 (12)0.0228 (12)0.0005 (11)0.0065 (10)0.0143 (10)
N10.0237 (14)0.0232 (14)0.0162 (13)0.0005 (10)0.0005 (10)0.0008 (10)
N20.0244 (14)0.0237 (12)0.0196 (14)0.0033 (10)0.0006 (11)0.0007 (10)
C10.0223 (16)0.0218 (14)0.0102 (14)0.0025 (12)0.0025 (11)0.0029 (11)
C20.0203 (15)0.0229 (14)0.0136 (14)0.0015 (12)0.0024 (11)0.0035 (11)
C30.0267 (17)0.0217 (14)0.0161 (15)0.0004 (12)0.0054 (12)0.0010 (12)
C40.0286 (17)0.0266 (15)0.0115 (14)0.0069 (13)0.0021 (12)0.0006 (12)
C50.0241 (17)0.0294 (16)0.0201 (16)0.0001 (13)0.0020 (13)0.0010 (13)
C60.0272 (17)0.0216 (15)0.0205 (16)0.0044 (12)0.0013 (13)0.0030 (12)
C70.0187 (15)0.0233 (14)0.0153 (15)0.0000 (12)0.0018 (11)0.0023 (11)
C80.0259 (17)0.0263 (15)0.0195 (16)0.0019 (13)0.0022 (13)0.0006 (12)
C90.0263 (17)0.0336 (17)0.0194 (16)0.0043 (13)0.0070 (13)0.0016 (13)
C100.0181 (16)0.0358 (17)0.0211 (16)0.0007 (13)0.0054 (12)0.0097 (13)
C110.0237 (17)0.0229 (15)0.0281 (17)0.0049 (13)0.0020 (13)0.0051 (13)
C120.0217 (16)0.0264 (15)0.0193 (16)0.0016 (12)0.0000 (12)0.0011 (12)
C130.0199 (15)0.0212 (14)0.0174 (15)0.0032 (12)0.0026 (12)0.0019 (11)
C140.043 (2)0.0256 (16)0.0171 (16)0.0029 (14)0.0052 (14)0.0025 (12)
C150.064 (2)0.0313 (17)0.0140 (16)0.0036 (16)0.0114 (15)0.0002 (13)
C160.045 (2)0.0210 (15)0.0239 (17)0.0020 (14)0.0135 (14)0.0052 (13)
C170.0229 (16)0.0211 (14)0.0239 (17)0.0002 (12)0.0042 (12)0.0035 (12)
C180.0208 (16)0.0256 (15)0.0175 (15)0.0041 (12)0.0026 (12)0.0013 (12)
C190.0263 (16)0.0170 (13)0.0137 (14)0.0022 (12)0.0048 (12)0.0010 (11)
C200.0246 (17)0.0269 (15)0.0210 (16)0.0032 (13)0.0009 (12)0.0006 (12)
C210.0310 (18)0.0339 (17)0.0205 (16)0.0123 (14)0.0042 (13)0.0015 (13)
C220.0393 (19)0.0224 (15)0.0114 (15)0.0043 (13)0.0043 (13)0.0016 (11)
C230.0354 (19)0.0306 (16)0.0135 (15)0.0016 (14)0.0007 (13)0.0020 (12)
C240.0221 (16)0.0278 (15)0.0185 (15)0.0018 (12)0.0023 (12)0.0016 (12)
C250.0153 (15)0.0231 (14)0.0183 (15)0.0001 (11)0.0004 (11)0.0007 (12)
C260.0215 (16)0.0230 (14)0.0165 (15)0.0020 (12)0.0023 (12)0.0019 (11)
C270.0274 (17)0.0265 (16)0.0193 (16)0.0000 (13)0.0067 (13)0.0031 (12)
C280.0259 (17)0.0232 (15)0.0285 (17)0.0020 (13)0.0032 (13)0.0017 (13)
C290.0239 (17)0.0271 (15)0.0227 (16)0.0003 (13)0.0003 (13)0.0076 (12)
C300.0205 (16)0.0244 (14)0.0153 (15)0.0004 (12)0.0036 (12)0.0004 (11)
C310.0207 (16)0.0233 (14)0.0111 (14)0.0035 (12)0.0032 (11)0.0008 (11)
C320.0224 (16)0.0245 (15)0.0189 (16)0.0007 (12)0.0047 (12)0.0003 (12)
C330.0210 (16)0.0282 (16)0.0199 (16)0.0009 (12)0.0010 (12)0.0015 (12)
C340.0246 (16)0.0336 (17)0.0136 (15)0.0066 (13)0.0016 (12)0.0002 (12)
C350.0294 (17)0.0239 (15)0.0222 (16)0.0014 (13)0.0017 (13)0.0039 (12)
C360.0263 (17)0.0253 (15)0.0193 (15)0.0022 (13)0.0019 (13)0.0016 (12)
Cl1S0.0312 (5)0.0322 (4)0.0338 (5)0.0014 (3)0.0086 (3)0.0084 (3)
Cl2S0.0412 (5)0.0307 (4)0.0479 (6)0.0011 (4)0.0140 (4)0.0073 (4)
Cl3S0.0350 (5)0.0372 (4)0.0297 (4)0.0069 (3)0.0005 (3)0.0039 (3)
C1S0.0296 (18)0.0324 (17)0.0253 (17)0.0019 (14)0.0027 (13)0.0001 (14)
Geometric parameters (Å, º) top
Fe1—N21.653 (2)C14—H140.9500
Fe1—N11.657 (2)C15—C161.371 (4)
Fe1—P12.2420 (10)C15—H150.9500
Fe1—P22.2478 (11)C16—C171.376 (4)
P1—C131.829 (3)C17—C181.383 (4)
P1—C11.830 (3)C17—H170.9500
P1—C71.837 (3)C18—H180.9500
P2—C191.824 (3)C19—C241.394 (4)
P2—C251.825 (3)C19—C201.396 (4)
P2—C311.840 (3)C20—C211.384 (4)
F1—C41.361 (3)C20—H200.9500
F2—C101.369 (3)C21—C221.370 (4)
F3—C161.363 (3)C21—H210.9500
F4—C221.367 (3)C22—C231.365 (4)
F5—C281.362 (3)C23—C241.389 (4)
F6—C341.372 (3)C23—H230.9500
O1—N11.191 (3)C24—H240.9500
O2—N21.197 (3)C25—C261.395 (4)
C1—C21.384 (4)C25—C301.402 (4)
C1—C61.399 (4)C26—C271.390 (4)
C2—C31.396 (4)C26—H260.9500
C2—H20.9500C27—C281.367 (4)
C3—C41.362 (4)C27—H270.9500
C3—H30.9500C28—C291.381 (4)
C4—C51.375 (4)C29—C301.378 (4)
C5—C61.381 (4)C29—H290.9500
C5—H50.9500C30—H300.9500
C6—H60.9500C31—C321.390 (4)
C7—C121.393 (4)C31—C361.399 (4)
C7—C81.394 (4)C32—C331.383 (4)
C8—C91.387 (4)C32—H320.9500
C8—H80.9500C33—C341.366 (4)
C9—C101.369 (4)C33—H330.9500
C9—H90.9500C34—C351.374 (4)
C10—C111.371 (4)C35—C361.380 (4)
C11—C121.391 (4)C35—H350.9500
C11—H110.9500C36—H360.9500
C12—H120.9500Cl1S—C1S1.763 (3)
C13—C141.383 (4)Cl2S—C1S1.753 (3)
C13—C181.392 (4)Cl3S—C1S1.759 (3)
C14—C151.395 (4)C1S—H1S1.0000
N2—Fe1—N1127.02 (11)C15—C16—C17123.1 (3)
N2—Fe1—P1101.53 (9)C16—C17—C18117.8 (3)
N1—Fe1—P1108.49 (8)C16—C17—H17121.1
N2—Fe1—P2105.60 (9)C18—C17—H17121.1
N1—Fe1—P2104.96 (9)C17—C18—C13121.1 (3)
P1—Fe1—P2108.27 (4)C17—C18—H18119.5
C13—P1—C1104.24 (13)C13—C18—H18119.5
C13—P1—C7103.62 (13)C24—C19—C20118.5 (3)
C1—P1—C7101.25 (13)C24—C19—P2118.4 (2)
C13—P1—Fe1119.13 (10)C20—C19—P2123.1 (2)
C1—P1—Fe1117.95 (9)C21—C20—C19120.7 (3)
C7—P1—Fe1108.36 (9)C21—C20—H20119.6
C19—P2—C25103.27 (12)C19—C20—H20119.6
C19—P2—C31103.37 (13)C22—C21—C20118.4 (3)
C25—P2—C31103.19 (12)C22—C21—H21120.8
C19—P2—Fe1117.89 (10)C20—C21—H21120.8
C25—P2—Fe1118.31 (9)C23—C22—F4118.2 (3)
C31—P2—Fe1108.92 (9)C23—C22—C21123.4 (3)
O1—N1—Fe1177.0 (2)F4—C22—C21118.4 (3)
O2—N2—Fe1178.1 (2)C22—C23—C24117.8 (3)
C2—C1—C6118.7 (3)C22—C23—H23121.1
C2—C1—P1121.9 (2)C24—C23—H23121.1
C6—C1—P1119.4 (2)C23—C24—C19121.2 (3)
C1—C2—C3121.1 (3)C23—C24—H24119.4
C1—C2—H2119.5C19—C24—H24119.4
C3—C2—H2119.5C26—C25—C30118.5 (3)
C4—C3—C2118.0 (3)C26—C25—P2123.1 (2)
C4—C3—H3121.0C30—C25—P2118.4 (2)
C2—C3—H3121.0C27—C26—C25120.7 (3)
F1—C4—C3119.0 (3)C27—C26—H26119.6
F1—C4—C5117.9 (3)C25—C26—H26119.6
C3—C4—C5123.1 (3)C28—C27—C26118.3 (3)
C4—C5—C6118.3 (3)C28—C27—H27120.8
C4—C5—H5120.8C26—C27—H27120.8
C6—C5—H5120.8F5—C28—C27118.8 (3)
C5—C6—C1120.8 (3)F5—C28—C29118.0 (3)
C5—C6—H6119.6C27—C28—C29123.2 (3)
C1—C6—H6119.6C30—C29—C28117.9 (3)
C12—C7—C8119.1 (3)C30—C29—H29121.0
C12—C7—P1124.2 (2)C28—C29—H29121.0
C8—C7—P1116.6 (2)C29—C30—C25121.3 (3)
C9—C8—C7120.9 (3)C29—C30—H30119.4
C9—C8—H8119.6C25—C30—H30119.4
C7—C8—H8119.6C32—C31—C36118.9 (3)
C10—C9—C8118.0 (3)C32—C31—P2124.2 (2)
C10—C9—H9121.0C36—C31—P2116.9 (2)
C8—C9—H9121.0C33—C32—C31120.6 (3)
F2—C10—C9118.3 (3)C33—C32—H32119.7
F2—C10—C11118.3 (3)C31—C32—H32119.7
C9—C10—C11123.4 (3)C34—C33—C32118.4 (3)
C10—C11—C12118.2 (3)C34—C33—H33120.8
C10—C11—H11120.9C32—C33—H33120.8
C12—C11—H11120.9C33—C34—F6118.7 (3)
C11—C12—C7120.4 (3)C33—C34—C35123.3 (3)
C11—C12—H12119.8F6—C34—C35117.9 (3)
C7—C12—H12119.8C34—C35—C36117.9 (3)
C14—C13—C18119.2 (3)C34—C35—H35121.0
C14—C13—P1123.7 (2)C36—C35—H35121.0
C18—C13—P1117.0 (2)C35—C36—C31120.8 (3)
C13—C14—C15120.6 (3)C35—C36—H36119.6
C13—C14—H14119.7C31—C36—H36119.6
C15—C14—H14119.7Cl2S—C1S—Cl3S110.41 (17)
C16—C15—C14118.1 (3)Cl2S—C1S—Cl1S110.44 (17)
C16—C15—H15121.0Cl3S—C1S—Cl1S111.10 (17)
C14—C15—H15121.0Cl2S—C1S—H1S108.3
F3—C16—C15118.5 (3)Cl3S—C1S—H1S108.3
F3—C16—C17118.3 (3)Cl1S—C1S—H1S108.3
N2—Fe1—P1—C1382.58 (13)P1—C13—C14—C15178.0 (3)
N1—Fe1—P1—C13141.68 (13)C13—C14—C15—C160.1 (5)
P2—Fe1—P1—C1328.29 (11)C14—C15—C16—F3179.9 (3)
N2—Fe1—P1—C1149.51 (13)C14—C15—C16—C170.2 (5)
N1—Fe1—P1—C113.77 (13)F3—C16—C17—C18179.3 (3)
P2—Fe1—P1—C199.61 (10)C15—C16—C17—C180.7 (5)
N2—Fe1—P1—C735.38 (12)C16—C17—C18—C131.7 (4)
N1—Fe1—P1—C7100.36 (13)C14—C13—C18—C172.0 (4)
P2—Fe1—P1—C7146.25 (10)P1—C13—C18—C17179.1 (2)
N2—Fe1—P2—C19175.56 (13)C25—P2—C19—C2488.2 (2)
N1—Fe1—P2—C1948.24 (13)C31—P2—C19—C24164.5 (2)
P1—Fe1—P2—C1967.47 (11)Fe1—P2—C19—C2444.3 (2)
N2—Fe1—P2—C2550.12 (13)C25—P2—C19—C2089.7 (2)
N1—Fe1—P2—C25173.69 (13)C31—P2—C19—C2017.6 (3)
P1—Fe1—P2—C2557.98 (11)Fe1—P2—C19—C20137.8 (2)
N2—Fe1—P2—C3167.18 (13)C24—C19—C20—C210.9 (4)
N1—Fe1—P2—C3169.01 (12)P2—C19—C20—C21178.8 (2)
P1—Fe1—P2—C31175.28 (9)C19—C20—C21—C220.4 (4)
C13—P1—C1—C2112.3 (2)C20—C21—C22—C230.0 (5)
C7—P1—C1—C2140.4 (2)C20—C21—C22—F4179.6 (3)
Fe1—P1—C1—C222.4 (3)F4—C22—C23—C24179.5 (2)
C13—P1—C1—C667.8 (2)C21—C22—C23—C240.1 (5)
C7—P1—C1—C639.5 (2)C22—C23—C24—C190.5 (4)
Fe1—P1—C1—C6157.51 (19)C20—C19—C24—C230.9 (4)
C6—C1—C2—C30.3 (4)P2—C19—C24—C23179.0 (2)
P1—C1—C2—C3179.7 (2)C19—P2—C25—C267.5 (3)
C1—C2—C3—C40.7 (4)C31—P2—C25—C26114.9 (2)
C2—C3—C4—F1178.7 (2)Fe1—P2—C25—C26124.8 (2)
C2—C3—C4—C50.5 (4)C19—P2—C25—C30173.6 (2)
F1—C4—C5—C6179.2 (2)C31—P2—C25—C3066.2 (2)
C3—C4—C5—C60.1 (4)Fe1—P2—C25—C3054.1 (2)
C4—C5—C6—C10.4 (4)C30—C25—C26—C270.2 (4)
C2—C1—C6—C50.2 (4)P2—C25—C26—C27179.1 (2)
P1—C1—C6—C5179.7 (2)C25—C26—C27—C281.2 (4)
C13—P1—C7—C120.2 (3)C26—C27—C28—F5179.2 (3)
C1—P1—C7—C12108.0 (3)C26—C27—C28—C291.2 (5)
Fe1—P1—C7—C12127.2 (2)F5—C28—C29—C30179.3 (3)
C13—P1—C7—C8178.8 (2)C27—C28—C29—C300.3 (5)
C1—P1—C7—C873.3 (2)C28—C29—C30—C251.8 (4)
Fe1—P1—C7—C851.4 (2)C26—C25—C30—C291.8 (4)
C12—C7—C8—C91.3 (4)P2—C25—C30—C29179.3 (2)
P1—C7—C8—C9180.0 (2)C19—P2—C31—C32103.9 (2)
C7—C8—C9—C102.5 (4)C25—P2—C31—C323.4 (3)
C8—C9—C10—F2178.0 (3)Fe1—P2—C31—C32130.0 (2)
C8—C9—C10—C112.1 (5)C19—P2—C31—C3676.6 (2)
F2—C10—C11—C12179.7 (2)C25—P2—C31—C36176.1 (2)
C9—C10—C11—C120.4 (5)Fe1—P2—C31—C3649.6 (2)
C10—C11—C12—C70.9 (4)C36—C31—C32—C330.0 (4)
C8—C7—C12—C110.4 (4)P2—C31—C32—C33179.5 (2)
P1—C7—C12—C11178.2 (2)C31—C32—C33—C340.7 (4)
C1—P1—C13—C148.4 (3)C32—C33—C34—F6178.3 (2)
C7—P1—C13—C14114.0 (3)C32—C33—C34—C350.4 (4)
Fe1—P1—C13—C14125.6 (2)C33—C34—C35—C360.5 (4)
C1—P1—C13—C18174.7 (2)F6—C34—C35—C36179.3 (2)
C7—P1—C13—C1869.1 (2)C34—C35—C36—C311.2 (4)
Fe1—P1—C13—C1851.3 (2)C32—C31—C36—C350.9 (4)
C18—C13—C14—C151.2 (5)P2—C31—C36—C35179.5 (2)

Experimental details

Crystal data
Chemical formula[Fe(NO)2(C18H12F3P)2]·CHCl3
Mr867.73
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)13.994 (5), 15.746 (6), 16.716 (6)
β (°) 97.651 (8)
V3)3651 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.79
Crystal size (mm)0.44 × 0.22 × 0.04
Data collection
DiffractometerBruker APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.721, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
22634, 6325, 5006
Rint0.056
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.115, 1.02
No. of reflections6325
No. of parameters478
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.24, 0.46

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We are grateful to the US Department of Education (GAANN Fellowship to MWJ; P200A030196), and the National Science Foundation (CHE-0076640 and CHE-0911537) for funding this work. The authors thank the National Science Foundation (CHE-0130835) and the University of Oklahoma for funds to acquire the diffractometer and computers used in this work.

References

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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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