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A new ferrocene complex, 16-ferrocenylmethyl-3β-hy­droxy­estra-1,3,5(10)-trien-17-one, has been synthesized and structurally characterized by single-crystal X-ray diffraction techniques. The ferrocenylmethyl group is positioned at the β face of the estrone moiety; as a result, a new stereogenic center is formed leading to an R stereochemical configuration. No head-to-tail hydrogen bonding is observed in the crystal packing, as is the case in estrone and other derivatives.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016008446/bg2586sup1.cif
Contains datablock I

CCDC reference: 1479699

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.043
  • wR factor = 0.097
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

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Alert level C PLAT090_ALERT_3_C Poor Data / Parameter Ratio (Zmax > 18) ........ 8.81 Note PLAT213_ALERT_2_C Atom C29 has ADP max/min Ratio ..... 3.3 prolat PLAT220_ALERT_2_C Non-Solvent Resd 1 C Ueq(max)/Ueq(min) Range 3.6 Ratio PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C29 Check PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00658 Ang.
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT791_ALERT_4_G The Model has Chirality at C8 (Chiral SPGR) R Verify PLAT791_ALERT_4_G The Model has Chirality at C9 (Chiral SPGR) S Verify PLAT791_ALERT_4_G The Model has Chirality at C13 (Chiral SPGR) S Verify PLAT791_ALERT_4_G The Model has Chirality at C14 (Chiral SPGR) S Verify PLAT791_ALERT_4_G The Model has Chirality at C16 (Chiral SPGR) R Verify
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

16-Ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one dimethyl sulfoxide monosolvate top
Crystal data top
[Fe(C5H5)(C24H27O2)]·C2H6OSF(000) = 580
Mr = 546.52Dx = 1.352 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.4178 (12) ÅCell parameters from 4213 reflections
b = 11.2436 (15) Åθ = 3.0–26.2°
c = 16.1160 (18) ŵ = 0.67 mm1
β = 93.148 (4)°T = 100 K
V = 1342.1 (3) Å3Block, yellow
Z = 20.3 × 0.25 × 0.03 mm
Data collection top
Bruker APEXII Ultra
diffractometer
5327 independent reflections
Radiation source: Micro Focus Rotating Anode, Bruker TXS4816 reflections with I > 2σ(I)
Double Bounce Multilayer Mirrors monochromatorRint = 0.048
Detector resolution: 7.9 pixels mm-1θmax = 26.4°, θmin = 2.2°
ω and φ scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 1314
Tmin = 0.064, Tmax = 0.093l = 2019
9583 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.0266P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.32 e Å3
5327 reflectionsΔρmin = 0.44 e Å3
329 parametersAbsolute structure: Flack x determined using 1990 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.004 (14)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.29444 (8)0.50023 (5)1.06433 (3)0.01977 (16)
S10.26603 (16)0.46255 (9)0.35262 (6)0.0224 (3)
O30.1244 (5)0.4378 (3)0.41388 (17)0.0285 (8)
O20.2299 (4)0.2860 (3)0.79220 (17)0.0247 (7)
O10.9351 (4)0.6126 (3)0.47762 (17)0.0232 (7)
H10.98860.55480.45690.035*
C170.1502 (6)0.3780 (4)0.7790 (2)0.0176 (9)
C130.0422 (6)0.3895 (4)0.7523 (2)0.0181 (9)
C80.2258 (6)0.5542 (4)0.6908 (2)0.0163 (9)
H80.31080.54840.74100.020*
C150.0744 (6)0.5880 (4)0.7724 (2)0.0188 (9)
H15A0.11750.66290.74580.023*
H15B0.00550.60680.82510.023*
C140.0394 (5)0.5159 (4)0.7143 (2)0.0170 (8)
H140.03470.50950.66080.020*
C220.0406 (7)0.4352 (4)1.0540 (3)0.0219 (10)
H220.02030.38091.09100.026*
C50.5284 (6)0.6214 (4)0.5951 (2)0.0166 (9)
C100.4657 (5)0.5020 (4)0.58935 (19)0.0168 (8)
C210.1534 (6)0.4044 (4)0.9831 (3)0.0202 (10)
H210.18110.32590.96460.024*
C240.1427 (7)0.6073 (4)0.9925 (3)0.0212 (10)
H240.16190.68940.98110.025*
C120.1022 (6)0.3007 (4)0.6877 (2)0.0225 (10)
H12A0.01110.29780.64050.027*
H12B0.11120.22040.71270.027*
C20.7268 (6)0.4550 (4)0.5087 (2)0.0198 (9)
H20.79450.39800.48000.024*
C70.2328 (7)0.6806 (4)0.6564 (3)0.0195 (10)
H7A0.16000.68540.60310.023*
H7B0.18130.73680.69600.023*
C190.3372 (5)0.5193 (4)0.8660 (2)0.0208 (9)
H19A0.39820.59760.86410.025*
H19B0.43160.45710.86710.025*
C300.1457 (6)0.4879 (5)0.2554 (2)0.0270 (10)
H30A0.08240.41500.23750.041*
H30B0.23080.51060.21370.041*
H30C0.05780.55190.26150.041*
C10.5698 (6)0.4215 (4)0.5459 (2)0.0200 (9)
H1A0.53170.34100.54170.024*
C110.2860 (6)0.3367 (4)0.6560 (3)0.0218 (10)
H11A0.38010.32740.70150.026*
H11B0.31640.28270.61030.026*
C200.2179 (5)0.5112 (5)0.9444 (2)0.0184 (9)
C30.7837 (6)0.5728 (4)0.5137 (2)0.0192 (10)
C160.2314 (5)0.5037 (4)0.7870 (2)0.0200 (8)
H160.32050.51400.73860.024*
C60.4272 (6)0.7143 (4)0.6427 (2)0.0193 (9)
H6A0.42830.79040.61190.023*
H6B0.49160.72720.69740.023*
C40.6851 (6)0.6544 (4)0.5575 (2)0.0182 (9)
H40.72570.73440.56190.022*
C290.3916 (9)0.5424 (7)1.1756 (3)0.059 (2)
H290.32440.58031.22000.071*
C310.3441 (7)0.6100 (4)0.3730 (3)0.0266 (11)
H31A0.24070.66240.38040.040*
H31B0.41110.63830.32610.040*
H31C0.42350.61060.42360.040*
C180.1621 (6)0.3784 (4)0.8337 (2)0.0225 (10)
H18A0.12840.44010.87280.034*
H18B0.28910.38810.82140.034*
H18C0.14450.29980.85840.034*
C230.0348 (6)0.5606 (4)1.0600 (2)0.0224 (10)
H230.02990.60551.10180.027*
C280.4933 (9)0.5984 (6)1.1132 (4)0.0490 (17)
H280.50900.68191.10790.059*
C90.2869 (6)0.4657 (4)0.6246 (2)0.0177 (9)
H90.19410.46980.57730.021*
C260.5157 (9)0.4035 (6)1.0890 (4)0.0523 (18)
H260.54830.32941.06420.063*
C270.5681 (6)0.5152 (7)1.0601 (3)0.0412 (14)
H270.64320.53111.01170.049*
C250.4046 (9)0.4208 (7)1.1623 (4)0.059 (2)
H250.34930.36031.19600.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0179 (3)0.0243 (3)0.0174 (3)0.0018 (3)0.0034 (2)0.0014 (3)
S10.0250 (6)0.0214 (6)0.0210 (5)0.0067 (5)0.0035 (4)0.0027 (4)
O30.039 (2)0.0249 (18)0.0233 (15)0.0017 (15)0.0130 (14)0.0014 (13)
O20.0264 (19)0.0243 (17)0.0239 (16)0.0099 (15)0.0072 (14)0.0039 (13)
O10.0227 (18)0.0230 (17)0.0243 (16)0.0023 (14)0.0042 (13)0.0020 (13)
C170.019 (2)0.023 (2)0.0106 (18)0.0015 (19)0.0024 (16)0.0033 (17)
C130.020 (2)0.018 (2)0.016 (2)0.0036 (19)0.0002 (17)0.0001 (17)
C80.019 (2)0.016 (2)0.0147 (18)0.0000 (18)0.0002 (16)0.0002 (16)
C150.020 (2)0.018 (2)0.018 (2)0.0025 (19)0.0000 (17)0.0006 (17)
C140.019 (2)0.018 (2)0.0145 (17)0.0011 (19)0.0001 (14)0.0002 (17)
C220.021 (3)0.025 (3)0.020 (2)0.006 (2)0.0048 (19)0.0007 (19)
C50.019 (2)0.019 (2)0.0121 (19)0.0009 (18)0.0024 (16)0.0005 (16)
C100.020 (2)0.0190 (19)0.0116 (16)0.001 (2)0.0015 (14)0.002 (2)
C210.022 (3)0.023 (2)0.016 (2)0.003 (2)0.0014 (18)0.0052 (18)
C240.019 (2)0.020 (2)0.024 (2)0.003 (2)0.0042 (19)0.0035 (19)
C120.026 (3)0.018 (2)0.024 (2)0.007 (2)0.0057 (19)0.0033 (18)
C20.024 (2)0.019 (2)0.0165 (19)0.0005 (19)0.0031 (17)0.0040 (17)
C70.024 (3)0.017 (2)0.018 (2)0.0002 (19)0.0030 (18)0.0009 (17)
C190.014 (2)0.027 (3)0.0211 (18)0.001 (2)0.0012 (15)0.0017 (19)
C300.029 (2)0.029 (3)0.0219 (19)0.002 (2)0.0025 (17)0.000 (2)
C10.025 (2)0.019 (2)0.0168 (19)0.0036 (19)0.0014 (17)0.0016 (17)
C110.028 (3)0.016 (2)0.022 (2)0.005 (2)0.0076 (19)0.0018 (18)
C200.0141 (19)0.025 (2)0.0164 (17)0.001 (2)0.0029 (14)0.0025 (19)
C30.018 (2)0.025 (2)0.0145 (19)0.0017 (19)0.0002 (17)0.0051 (18)
C160.017 (2)0.025 (2)0.0171 (17)0.000 (2)0.0013 (15)0.000 (2)
C60.026 (2)0.014 (2)0.018 (2)0.0020 (18)0.0011 (17)0.0023 (17)
C40.022 (2)0.017 (2)0.0158 (19)0.0018 (18)0.0022 (17)0.0018 (16)
C290.030 (3)0.121 (7)0.029 (3)0.024 (4)0.018 (2)0.026 (3)
C310.027 (3)0.028 (3)0.024 (2)0.007 (2)0.0020 (19)0.001 (2)
C180.022 (2)0.024 (2)0.021 (2)0.006 (2)0.0005 (18)0.0057 (18)
C230.017 (3)0.033 (3)0.017 (2)0.003 (2)0.0016 (18)0.003 (2)
C280.033 (4)0.043 (4)0.074 (4)0.003 (3)0.033 (3)0.009 (3)
C90.024 (2)0.016 (2)0.0133 (17)0.0004 (18)0.0009 (16)0.0023 (16)
C260.040 (4)0.053 (4)0.067 (4)0.028 (3)0.030 (3)0.022 (3)
C270.018 (2)0.076 (5)0.030 (2)0.004 (3)0.0067 (19)0.006 (3)
C250.039 (4)0.092 (6)0.049 (4)0.016 (4)0.020 (3)0.048 (4)
Geometric parameters (Å, º) top
Fe1—C222.035 (5)C12—H12A0.9900
Fe1—C212.030 (4)C12—H12B0.9900
Fe1—C242.049 (5)C12—C111.536 (6)
Fe1—C202.047 (3)C2—H20.9500
Fe1—C292.026 (5)C2—C11.391 (6)
Fe1—C232.047 (5)C2—C31.392 (6)
Fe1—C282.035 (6)C7—H7A0.9900
Fe1—C262.026 (6)C7—H7B0.9900
Fe1—C272.035 (5)C7—C61.518 (6)
Fe1—C252.025 (6)C19—H19A0.9900
S1—O31.506 (3)C19—H19B0.9900
S1—C301.783 (4)C19—C201.505 (5)
S1—C311.781 (4)C19—C161.543 (5)
O2—C171.216 (5)C30—H30A0.9800
O1—H10.8400C30—H30B0.9800
O1—C31.368 (5)C30—H30C0.9800
C17—C131.518 (6)C1—H1A0.9500
C17—C161.545 (6)C11—H11A0.9900
C13—C141.548 (6)C11—H11B0.9900
C13—C121.527 (5)C11—C91.536 (6)
C13—C181.548 (5)C3—C41.389 (6)
C8—H81.0000C16—H161.0000
C8—C141.516 (5)C6—H6A0.9900
C8—C71.527 (6)C6—H6B0.9900
C8—C91.545 (5)C4—H40.9500
C15—H15A0.9900C29—H290.9500
C15—H15B0.9900C29—C281.376 (9)
C15—C141.527 (5)C29—C251.387 (10)
C15—C161.529 (6)C31—H31A0.9800
C14—H141.0000C31—H31B0.9800
C22—H220.9500C31—H31C0.9800
C22—C211.422 (6)C18—H18A0.9800
C22—C231.414 (6)C18—H18B0.9800
C5—C101.422 (6)C18—H18C0.9800
C5—C61.519 (6)C23—H230.9500
C5—C41.390 (6)C28—H280.9500
C10—C11.402 (6)C28—C271.365 (9)
C10—C91.527 (5)C9—H91.0000
C21—H210.9500C26—H260.9500
C21—C201.423 (7)C26—C271.387 (10)
C24—H240.9500C26—C251.416 (9)
C24—C201.425 (6)C27—H270.9500
C24—C231.415 (6)C25—H250.9500
C22—Fe1—C2468.00 (19)C1—C2—C3119.4 (4)
C22—Fe1—C2068.81 (16)C3—C2—H2120.3
C22—Fe1—C2340.53 (16)C8—C7—H7A109.7
C22—Fe1—C28156.9 (2)C8—C7—H7B109.7
C21—Fe1—C2240.95 (17)H7A—C7—H7B108.2
C21—Fe1—C2468.24 (16)C6—C7—C8109.7 (4)
C21—Fe1—C2040.86 (19)C6—C7—H7A109.7
C21—Fe1—C2368.60 (19)C6—C7—H7B109.7
C21—Fe1—C28161.4 (2)H19A—C19—H19B107.8
C21—Fe1—C27124.8 (2)C20—C19—H19A109.1
C20—Fe1—C2440.73 (18)C20—C19—H19B109.1
C29—Fe1—C22122.2 (2)C20—C19—C16112.6 (3)
C29—Fe1—C21156.4 (3)C16—C19—H19A109.1
C29—Fe1—C24126.6 (2)C16—C19—H19B109.1
C29—Fe1—C20162.2 (3)S1—C30—H30A109.5
C29—Fe1—C23109.5 (2)S1—C30—H30B109.5
C29—Fe1—C2839.6 (3)S1—C30—H30C109.5
C29—Fe1—C2667.7 (3)H30A—C30—H30B109.5
C29—Fe1—C2766.9 (2)H30A—C30—H30C109.5
C29—Fe1—C2540.0 (3)H30B—C30—H30C109.5
C23—Fe1—C2440.42 (18)C10—C1—H1A118.7
C23—Fe1—C2068.75 (16)C2—C1—C10122.5 (4)
C28—Fe1—C24109.4 (2)C2—C1—H1A118.7
C28—Fe1—C20125.3 (2)C12—C11—H11A109.2
C28—Fe1—C23122.5 (2)C12—C11—H11B109.2
C26—Fe1—C22125.9 (3)H11A—C11—H11B107.9
C26—Fe1—C21107.1 (2)C9—C11—C12112.2 (4)
C26—Fe1—C24154.4 (2)C9—C11—H11A109.2
C26—Fe1—C20119.2 (2)C9—C11—H11B109.2
C26—Fe1—C23163.4 (3)C21—C20—Fe168.9 (2)
C26—Fe1—C2866.6 (2)C21—C20—C24106.9 (3)
C26—Fe1—C2739.9 (3)C21—C20—C19125.9 (4)
C27—Fe1—C22162.4 (2)C24—C20—Fe169.7 (2)
C27—Fe1—C24120.7 (2)C24—C20—C19127.3 (5)
C27—Fe1—C20106.95 (17)C19—C20—Fe1128.0 (3)
C27—Fe1—C23155.6 (2)O1—C3—C2122.7 (4)
C27—Fe1—C2839.2 (3)O1—C3—C4117.9 (4)
C25—Fe1—C22108.7 (2)C4—C3—C2119.4 (4)
C25—Fe1—C21120.9 (3)C17—C16—H16106.6
C25—Fe1—C24163.2 (3)C15—C16—C17104.5 (3)
C25—Fe1—C20155.1 (3)C15—C16—C19118.9 (3)
C25—Fe1—C23126.4 (2)C15—C16—H16106.6
C25—Fe1—C2866.7 (3)C19—C16—C17113.0 (4)
C25—Fe1—C2640.9 (3)C19—C16—H16106.6
C25—Fe1—C2767.5 (2)C5—C6—C7113.7 (3)
O3—S1—C30105.8 (2)C5—C6—H6A108.8
O3—S1—C31106.4 (2)C5—C6—H6B108.8
C31—S1—C3098.9 (2)C7—C6—H6A108.8
C3—O1—H1109.5C7—C6—H6B108.8
O2—C17—C13126.6 (4)H6A—C6—H6B107.7
O2—C17—C16124.6 (4)C5—C4—H4119.3
C13—C17—C16108.8 (4)C3—C4—C5121.4 (4)
C17—C13—C14101.4 (3)C3—C4—H4119.3
C17—C13—C12116.8 (3)Fe1—C29—H29125.0
C17—C13—C18105.0 (3)C28—C29—Fe170.6 (3)
C14—C13—C18113.8 (3)C28—C29—H29126.1
C12—C13—C14109.2 (3)C28—C29—C25107.9 (6)
C12—C13—C18110.5 (4)C25—C29—Fe169.9 (4)
C14—C8—H8108.7C25—C29—H29126.1
C14—C8—C7113.9 (4)S1—C31—H31A109.5
C14—C8—C9107.3 (3)S1—C31—H31B109.5
C7—C8—H8108.7S1—C31—H31C109.5
C7—C8—C9109.4 (3)H31A—C31—H31B109.5
C9—C8—H8108.7H31A—C31—H31C109.5
H15A—C15—H15B109.2H31B—C31—H31C109.5
C14—C15—H15A111.3C13—C18—H18A109.5
C14—C15—H15B111.3C13—C18—H18B109.5
C14—C15—C16102.5 (3)C13—C18—H18C109.5
C16—C15—H15A111.3H18A—C18—H18B109.5
C16—C15—H15B111.3H18A—C18—H18C109.5
C13—C14—H14105.7H18B—C18—H18C109.5
C8—C14—C13111.5 (3)Fe1—C23—H23126.3
C8—C14—C15123.1 (4)C22—C23—Fe169.3 (3)
C8—C14—H14105.7C22—C23—C24107.6 (4)
C15—C14—C13103.9 (3)C22—C23—H23126.2
C15—C14—H14105.7C24—C23—Fe169.9 (3)
Fe1—C22—H22126.2C24—C23—H23126.2
C21—C22—Fe169.3 (3)Fe1—C28—H28126.1
C21—C22—H22125.9C29—C28—Fe169.8 (4)
C23—C22—Fe170.2 (3)C29—C28—H28125.3
C23—C22—H22125.9C27—C28—Fe170.4 (3)
C23—C22—C21108.2 (4)C27—C28—C29109.4 (6)
C10—C5—C6120.9 (4)C27—C28—H28125.3
C4—C5—C10120.1 (4)C8—C9—H9106.3
C4—C5—C6119.0 (4)C10—C9—C8112.2 (3)
C5—C10—C9121.1 (4)C10—C9—C11113.3 (4)
C1—C10—C5117.1 (4)C10—C9—H9106.3
C1—C10—C9121.7 (4)C11—C9—C8111.9 (3)
Fe1—C21—H21125.8C11—C9—H9106.3
C22—C21—Fe169.7 (3)Fe1—C26—H26125.4
C22—C21—H21125.8C27—C26—Fe170.3 (3)
C22—C21—C20108.3 (4)C27—C26—H26126.4
C20—C21—Fe170.2 (2)C27—C26—C25107.2 (6)
C20—C21—H21125.8C25—C26—Fe169.5 (4)
Fe1—C24—H24126.8C25—C26—H26126.4
C20—C24—Fe169.6 (2)Fe1—C27—H27125.6
C20—C24—H24125.5C28—C27—Fe170.4 (3)
C23—C24—Fe169.7 (3)C28—C27—C26108.2 (5)
C23—C24—H24125.5C28—C27—H27125.9
C23—C24—C20108.9 (4)C26—C27—Fe169.7 (3)
C13—C12—H12A109.5C26—C27—H27125.9
C13—C12—H12B109.5Fe1—C25—H25125.6
C13—C12—C11110.6 (3)C29—C25—Fe170.0 (4)
H12A—C12—H12B108.1C29—C25—C26107.3 (6)
C11—C12—H12A109.5C29—C25—H25126.4
C11—C12—H12B109.5C26—C25—Fe169.6 (3)
C1—C2—H2120.3C26—C25—H25126.4
Fe1—C22—C21—C2059.8 (3)C7—C8—C9—C1050.4 (4)
Fe1—C22—C23—C2459.6 (3)C7—C8—C9—C11179.0 (4)
Fe1—C21—C20—C2459.6 (3)C1—C10—C9—C8162.9 (3)
Fe1—C21—C20—C19122.3 (4)C1—C10—C9—C1135.0 (5)
Fe1—C24—C20—C2159.1 (3)C1—C2—C3—O1179.0 (4)
Fe1—C24—C20—C19122.9 (4)C1—C2—C3—C41.5 (6)
Fe1—C24—C23—C2259.2 (4)C20—C24—C23—Fe158.6 (3)
Fe1—C29—C28—C2759.4 (4)C20—C24—C23—C220.5 (6)
Fe1—C29—C25—C2659.9 (4)C20—C19—C16—C1765.7 (5)
Fe1—C28—C27—C2659.7 (4)C20—C19—C16—C1557.3 (6)
Fe1—C26—C27—C2860.1 (4)C3—C2—C1—C100.4 (6)
Fe1—C26—C25—C2960.2 (5)C16—C17—C13—C1420.6 (4)
O2—C17—C13—C14159.3 (4)C16—C17—C13—C12139.1 (3)
O2—C17—C13—C1240.7 (6)C16—C17—C13—C1898.1 (4)
O2—C17—C13—C1882.0 (5)C16—C15—C14—C1343.4 (4)
O2—C17—C16—C15174.7 (4)C16—C15—C14—C8171.2 (3)
O2—C17—C16—C1944.1 (5)C16—C19—C20—Fe1169.8 (4)
O1—C3—C4—C5179.2 (4)C16—C19—C20—C2179.7 (5)
C17—C13—C14—C8173.9 (3)C16—C19—C20—C2497.9 (5)
C17—C13—C14—C1539.3 (4)C6—C5—C10—C1178.5 (3)
C17—C13—C12—C11170.1 (4)C6—C5—C10—C95.1 (5)
C13—C17—C16—C155.4 (4)C6—C5—C4—C3179.5 (3)
C13—C17—C16—C19136.0 (3)C4—C5—C10—C11.0 (5)
C13—C12—C11—C953.2 (5)C4—C5—C10—C9175.5 (3)
C8—C7—C6—C549.2 (4)C4—C5—C6—C7161.2 (4)
C14—C13—C12—C1155.8 (5)C29—C28—C27—Fe159.1 (4)
C14—C8—C7—C6174.5 (3)C29—C28—C27—C260.6 (6)
C14—C8—C9—C10174.3 (3)C18—C13—C14—C861.8 (4)
C14—C8—C9—C1157.1 (4)C18—C13—C14—C1572.8 (4)
C14—C15—C16—C1729.6 (4)C18—C13—C12—C1170.0 (4)
C14—C15—C16—C19156.7 (3)C23—C22—C21—Fe159.6 (4)
C22—C21—C20—Fe159.5 (3)C23—C22—C21—C200.2 (6)
C22—C21—C20—C240.1 (4)C23—C24—C20—Fe158.7 (3)
C22—C21—C20—C19178.1 (4)C23—C24—C20—C210.4 (5)
C5—C10—C1—C20.8 (6)C23—C24—C20—C19178.4 (4)
C5—C10—C9—C820.9 (5)C28—C29—C25—Fe160.7 (4)
C5—C10—C9—C11148.8 (3)C28—C29—C25—C260.8 (8)
C10—C5—C6—C719.3 (5)C9—C8—C14—C1361.4 (4)
C10—C5—C4—C30.0 (6)C9—C8—C14—C15174.1 (3)
C21—C22—C23—Fe159.1 (3)C9—C8—C7—C665.6 (4)
C21—C22—C23—C240.4 (6)C9—C10—C1—C2175.6 (4)
C12—C13—C14—C862.1 (4)C27—C26—C25—Fe160.5 (4)
C12—C13—C14—C15163.2 (3)C27—C26—C25—C290.4 (7)
C12—C11—C9—C854.3 (5)C25—C29—C28—Fe160.3 (5)
C12—C11—C9—C10177.6 (3)C25—C29—C28—C270.9 (7)
C2—C3—C4—C51.3 (6)C25—C26—C27—Fe160.0 (4)
C7—C8—C14—C13177.5 (3)C25—C26—C27—C280.2 (6)
C7—C8—C14—C1553.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.841.822.655 (5)174
Symmetry code: (i) x+1, y, z.
Selected geometrical parameters (Å, °) for compounds 1, 2 and 3 top
123
Bond lengths
Fe—C(Cp)avg2.029 (12)
Fe—C(Cp*)subt2.042 (10)
C(Cp)subt—CH21.505 (5)
C17—O21.219 (2)1.216 (5)1.215 (2)
C3—O11.374 (2)1.368 (5)1.371 (2)
Hydrogen-bond parameters
D—H0.860.840.84
H···A1.97 (O2···H1)1.82 [O3(DMSO)···H1]1.93 (O2···H1)
D···A2.819 (2) (O1···O2)2.655 (5) (O1···O3)2.760 (2) (O1···O2)
D—H···A174174170
Bond angles
C20—C19—C16112.6 (3)
O3—C1—C16108.4 (1)
Torsion angles
O2—C17—C16—C1944.1 (5)49.7 (2) O(2)—C(17)—C(16)—C(1)
 

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