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Chiral oxazolinyl-modified ferrocene­carboxyl­ic acid, (S,Sp)-[Fe{η5-C5H3(CO2H-1)(C6H10NO-2)}(η5-C5H5)] or [Fe(C5H5)(C12H14NO3)], crystallizes as a molecular compound, featuring an intramolecular O—H...N hydrogen bond between the carboxyl hydroxy group and oxazoline N atom, with an O...N separation of 2.559 (3) Å. The ferrocene substituents are rotated only slightly from the plane of their parent cyclo­penta­dienyl ring: 7.65 (17) (oxazoline) and 2.3 (3)° (carboxyl).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804002685/cv6269sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804002685/cv6269Isup2.hkl
Contains datablock I

CCDC reference: 236026

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.034
  • wR factor = 0.087
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.34 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.46 Ratio
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.21 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C15
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 3497 Count of symmetry unique reflns 1845 Completeness (_total/calc) 189.54% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1652 Fraction of Friedel pairs measured 0.895 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 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 1 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: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001).

(S,sp)-2-[4-(1-methylethyl)-4,5-dihydrooxazol-1-yl]ferrocenecarboxylic acid top
Crystal data top
[Fe(C5H5)(C12H14NO3)]Dx = 1.477 Mg m3
Mr = 341.18Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43Cell parameters from 1852 reflections
Hall symbol: P 4cwθ = 1.0–27.5°
a = 11.4599 (2) ŵ = 0.99 mm1
c = 11.6864 (2) ÅT = 150 K
V = 1534.77 (5) Å3Prism, brown
Z = 40.52 × 0.40 × 0.28 mm
F(000) = 712
Data collection top
Nonius KappaCCD
diffractometer
3497 independent reflections
Radiation source: fine-focus sealed tube3323 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.044
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω and φ scans to fill the Ewald sphereh = 1414
Absorption correction: multi-scan
(SORTAV; Blessing 1997)
k = 1414
Tmin = 0.681, Tmax = 0.757l = 1415
27433 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.048P)2 + 0.8632P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3497 reflectionsΔρmax = 0.71 e Å3
205 parametersΔρmin = 0.32 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.020 (17)
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.

————————————————————– Least-Squares Planes - P*X+Q*Y+R*Z=S ————————————————————– Nr 1 P Q R S ————————————————————– oxazo -.1653 (13). 9720 (4) -.1670 (15) 8.993 (8)

perpendicular distances of the defining atoms to the l.s.-plane O(3). 061 (2) N -.040 (2) C(12) -.014 (2) C(13). 070 (3) C(14) -.078 (3) ————————————————————– Nr 2 P Q R S ————————————————————– Cp1 -.0450 (14). 9925 (2) -.1134 (15) 9.752 (11)

perpendicular distances of the defining atoms to the l.s.-plane C(1) -.001 (2) C(2) -.002 (2) C(3). 001 (2) C(4) -.002 (3) C(5). 000 (3) ————————————————————– Nr 3 P Q R S ————————————————————– Cp2 -.0472 (14). 9953 (1) -.0850 (15) 6.636 (11)

perpendicular distances of the defining atoms to the l.s.-plane C(6). 001 (2) C(7). 002 (2) C(8) -.001 (2) C(9). 002 (3) C(10) -.001 (3) ————————————————————– Nr 4 P Q R S ————————————————————– COO -.022 (4). 9964 (1) -.0818 (18) 10.03 (2)

perpendicular distances of the defining atoms to the l.s.-plane O(1) -.001 (2) O(2) -.001 (2) C(11) -.001 (2) ————————————————————– Dihedral angles of the l.s.-planes

1,2 = 7.65 (17) 1,3 = 8.35 (17) 1,4 = 9.7 (3) 2,3 = 1.64 (17) 2,4 = 2.3 (3) 3,4 = 1.5 (3) ————————————————————–

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
Fe0.27611 (3)0.78048 (3)0.46928 (3)0.02614 (10)
N0.3220 (2)0.8863 (2)0.15844 (19)0.0327 (5)
O10.56936 (17)0.9282 (2)0.4460 (2)0.0440 (5)
O20.51445 (17)0.91199 (19)0.26653 (19)0.0378 (4)
O30.13067 (16)0.86941 (16)0.19636 (16)0.0322 (4)
C10.3664 (2)0.9224 (2)0.4157 (2)0.0293 (5)
C20.2577 (2)0.9102 (2)0.3544 (2)0.0267 (5)
C30.1646 (2)0.9157 (2)0.4355 (3)0.0329 (6)
H30.08540.91050.41910.039*
C40.2151 (3)0.9306 (3)0.5463 (3)0.0374 (6)
H40.17420.93640.61470.045*
C50.3380 (3)0.9350 (3)0.5344 (3)0.0369 (6)
H50.39130.94440.59370.044*
C60.3815 (2)0.6389 (2)0.4473 (3)0.0371 (7)
H60.45800.64030.42070.045*
C70.2805 (3)0.6282 (2)0.3784 (3)0.0340 (6)
H70.27880.62140.29920.041*
C80.1818 (2)0.6297 (2)0.4525 (3)0.0364 (6)
H80.10410.62380.43010.044*
C90.2228 (2)0.6419 (3)0.5663 (3)0.0378 (6)
H90.17680.64580.63180.045*
C100.3470 (2)0.6472 (3)0.5628 (3)0.0368 (6)
H100.39640.65470.62540.044*
C110.4911 (2)0.9207 (2)0.3766 (2)0.0309 (5)
C120.2410 (2)0.88777 (19)0.2324 (2)0.0271 (5)
C130.2686 (3)0.8672 (3)0.0449 (3)0.0387 (6)
H130.26780.94280.00570.046*
C140.1415 (3)0.8375 (3)0.0747 (2)0.0369 (6)
H14A0.08780.88250.02800.044*
H14B0.12610.75510.06340.044*
C150.3415 (3)0.7844 (3)0.0284 (4)0.0561 (8)
H150.41650.82180.04490.067*
C160.3641 (4)0.6706 (4)0.0296 (4)0.0666 (11)
H16A0.29130.63210.04460.100*
H16B0.40420.68430.10050.100*
H16C0.41150.62240.01890.100*
C170.2788 (6)0.7613 (7)0.1415 (5)0.116 (3)
H17A0.33120.72320.19360.174*
H17B0.25350.83400.17400.174*
H17C0.21240.71220.12810.174*
H900.450 (5)0.905 (5)0.211 (6)0.107 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe0.02504 (17)0.02835 (18)0.02503 (16)0.00284 (14)0.00033 (15)0.00254 (15)
N0.0330 (11)0.0366 (12)0.0285 (12)0.0015 (9)0.0041 (9)0.0003 (9)
O10.0311 (10)0.0543 (12)0.0466 (13)0.0079 (9)0.0107 (9)0.0023 (10)
O20.0277 (9)0.0472 (11)0.0385 (10)0.0040 (8)0.0017 (8)0.0037 (9)
O30.0307 (9)0.0336 (9)0.0321 (10)0.0042 (7)0.0071 (7)0.0012 (8)
C10.0296 (12)0.0258 (12)0.0324 (13)0.0046 (10)0.0019 (10)0.0040 (10)
C20.0259 (12)0.0236 (11)0.0307 (13)0.0003 (9)0.0010 (10)0.0017 (10)
C30.0279 (12)0.0302 (12)0.0406 (15)0.0018 (10)0.0029 (10)0.0073 (10)
C40.0383 (15)0.0393 (15)0.0347 (14)0.0004 (11)0.0045 (12)0.0123 (12)
C50.0413 (15)0.0357 (14)0.0337 (14)0.0041 (12)0.0036 (12)0.0105 (11)
C60.0305 (13)0.0301 (12)0.0508 (19)0.0008 (10)0.0051 (12)0.0011 (12)
C70.0417 (15)0.0228 (12)0.0376 (15)0.0016 (11)0.0021 (12)0.0070 (11)
C80.0284 (12)0.0305 (12)0.0502 (18)0.0078 (10)0.0099 (12)0.0056 (12)
C90.0330 (14)0.0418 (15)0.0386 (16)0.0040 (11)0.0001 (12)0.0113 (13)
C100.0292 (13)0.0412 (15)0.0399 (16)0.0002 (11)0.0082 (12)0.0106 (12)
C110.0279 (12)0.0246 (12)0.0403 (15)0.0030 (9)0.0025 (11)0.0023 (10)
C120.0295 (11)0.0201 (10)0.0318 (13)0.0000 (8)0.0010 (10)0.0017 (10)
C130.0435 (15)0.0457 (16)0.0269 (13)0.0049 (12)0.0088 (12)0.0010 (12)
C140.0451 (16)0.0380 (14)0.0277 (14)0.0084 (12)0.0089 (12)0.0003 (11)
C150.062 (2)0.064 (2)0.0431 (17)0.0021 (17)0.004 (2)0.0102 (17)
C160.077 (3)0.054 (2)0.070 (3)0.0010 (19)0.004 (2)0.0123 (19)
C170.118 (5)0.184 (7)0.047 (3)0.056 (5)0.028 (3)0.055 (4)
Geometric parameters (Å, º) top
Fe—C22.014 (3)C5—H50.9300
Fe—C12.027 (3)C6—C101.409 (5)
Fe—C62.039 (3)C6—C71.415 (4)
Fe—C72.043 (3)C6—H60.9300
Fe—C92.045 (3)C7—C81.425 (4)
Fe—C102.046 (3)C7—H70.9300
Fe—C32.047 (3)C8—C91.418 (4)
Fe—C82.047 (3)C8—H80.9300
Fe—C52.053 (3)C9—C101.425 (4)
Fe—C42.063 (3)C9—H90.9300
N—C121.269 (3)C10—H100.9300
N—C131.477 (4)C13—C151.527 (5)
O1—C111.213 (3)C13—C141.536 (4)
O2—C111.317 (4)C13—H130.9800
O2—H900.98 (7)C14—H14A0.9700
O3—C121.349 (3)C14—H14B0.9700
O3—C141.473 (3)C15—C161.493 (6)
C1—C51.433 (4)C15—C171.528 (6)
C1—C21.444 (4)C15—H150.9800
C1—C111.500 (4)C16—H16A0.9600
C2—C31.428 (4)C16—H16B0.9600
C2—C121.461 (4)C16—H16C0.9600
C3—C41.428 (4)C17—H17A0.9600
C3—H30.9300C17—H17B0.9600
C4—C51.416 (4)C17—H17C0.9600
C4—H40.9300
C2—Fe—C141.87 (10)C4—C5—C1108.5 (3)
C2—Fe—C6124.42 (12)C4—C5—Fe70.25 (16)
C1—Fe—C6107.27 (11)C1—C5—Fe68.46 (16)
C2—Fe—C7106.64 (11)C4—C5—H5125.8
C1—Fe—C7120.81 (11)C1—C5—H5125.8
C6—Fe—C740.58 (12)Fe—C5—H5127.1
C2—Fe—C9155.72 (11)C10—C6—C7108.7 (3)
C1—Fe—C9161.28 (11)C10—C6—Fe70.09 (16)
C6—Fe—C968.23 (12)C7—C6—Fe69.88 (15)
C7—Fe—C968.43 (12)C10—C6—H6125.7
C2—Fe—C10161.54 (11)C7—C6—H6125.7
C1—Fe—C10124.16 (11)Fe—C6—H6125.9
C6—Fe—C1040.37 (13)C6—C7—C8107.7 (3)
C7—Fe—C1068.29 (13)C6—C7—Fe69.54 (15)
C9—Fe—C1040.77 (11)C8—C7—Fe69.78 (15)
C2—Fe—C341.17 (11)C6—C7—H7126.2
C1—Fe—C369.61 (11)C8—C7—H7126.2
C6—Fe—C3161.42 (12)Fe—C7—H7126.1
C7—Fe—C3124.17 (12)C9—C8—C7107.9 (2)
C9—Fe—C3120.56 (12)C9—C8—Fe69.62 (16)
C10—Fe—C3156.34 (12)C7—C8—Fe69.45 (14)
C2—Fe—C8120.23 (11)C9—C8—H8126.0
C1—Fe—C8156.50 (12)C7—C8—H8126.0
C6—Fe—C868.26 (11)Fe—C8—H8126.5
C7—Fe—C840.76 (12)C8—C9—C10107.9 (3)
C9—Fe—C840.55 (12)C8—C9—Fe69.83 (16)
C10—Fe—C868.33 (11)C10—C9—Fe69.66 (16)
C3—Fe—C8106.89 (11)C8—C9—H9126.0
C2—Fe—C569.34 (11)C10—C9—H9126.0
C1—Fe—C541.10 (11)Fe—C9—H9126.1
C6—Fe—C5121.86 (12)C6—C10—C9107.8 (3)
C7—Fe—C5156.99 (12)C6—C10—Fe69.54 (16)
C9—Fe—C5124.54 (13)C9—C10—Fe69.57 (16)
C10—Fe—C5107.97 (13)C6—C10—H10126.1
C3—Fe—C568.56 (12)C9—C10—H10126.1
C8—Fe—C5160.97 (13)Fe—C10—H10126.4
C2—Fe—C468.89 (12)O1—C11—O2120.6 (3)
C1—Fe—C468.82 (12)O1—C11—C1120.0 (3)
C6—Fe—C4156.78 (12)O2—C11—C1119.5 (2)
C7—Fe—C4161.25 (11)N—C12—O3118.1 (2)
C9—Fe—C4107.72 (13)N—C12—C2124.8 (2)
C10—Fe—C4121.61 (14)O3—C12—C2117.0 (2)
C3—Fe—C440.66 (12)N—C13—C15111.7 (3)
C8—Fe—C4124.50 (12)N—C13—C14102.9 (2)
C5—Fe—C440.23 (12)C15—C13—C14120.6 (3)
C12—N—C13108.1 (2)N—C13—H13107.0
C11—O2—H90120 (4)C15—C13—H13107.0
C12—O3—C14105.1 (2)C14—C13—H13107.0
C5—C1—C2107.1 (2)O3—C14—C13104.1 (2)
C5—C1—C11120.8 (2)O3—C14—H14A110.9
C2—C1—C11132.0 (2)C13—C14—H14A110.9
C5—C1—Fe70.44 (17)O3—C14—H14B110.9
C2—C1—Fe68.59 (14)C13—C14—H14B110.9
C11—C1—Fe124.74 (18)H14A—C14—H14B109.0
C3—C2—C1108.1 (2)C16—C15—C13112.5 (4)
C3—C2—C12123.9 (2)C16—C15—C17108.9 (4)
C1—C2—C12127.9 (2)C13—C15—C17109.6 (3)
C3—C2—Fe70.63 (16)C16—C15—H15108.6
C1—C2—Fe69.54 (15)C13—C15—H15108.6
C12—C2—Fe122.30 (17)C17—C15—H15108.6
C4—C3—C2107.7 (2)C15—C16—H16A109.5
C4—C3—Fe70.29 (16)C15—C16—H16B109.5
C2—C3—Fe68.20 (15)H16A—C16—H16B109.5
C4—C3—H3126.1C15—C16—H16C109.5
C2—C3—H3126.1H16A—C16—H16C109.5
Fe—C3—H3126.9H16B—C16—H16C109.5
C5—C4—C3108.6 (3)C15—C17—H17A109.5
C5—C4—Fe69.51 (16)C15—C17—H17B109.5
C3—C4—Fe69.05 (16)H17A—C17—H17B109.5
C5—C4—H4125.7C15—C17—H17C109.5
C3—C4—H4125.7H17A—C17—H17C109.5
Fe—C4—H4127.3H17B—C17—H17C109.5
C2—Fe—C1—C5118.3 (2)C4—Fe—C5—C1120.3 (3)
C6—Fe—C1—C5118.98 (18)C2—Fe—C6—C10165.75 (16)
C7—Fe—C1—C5161.20 (17)C1—Fe—C6—C10122.82 (17)
C9—Fe—C1—C546.0 (4)C7—Fe—C6—C10119.7 (2)
C10—Fe—C1—C577.8 (2)C9—Fe—C6—C1037.88 (17)
C3—Fe—C1—C580.38 (18)C3—Fe—C6—C10159.9 (3)
C8—Fe—C1—C5166.0 (2)C8—Fe—C6—C1081.69 (18)
C4—Fe—C1—C536.75 (18)C5—Fe—C6—C1080.2 (2)
C6—Fe—C1—C2122.68 (16)C4—Fe—C6—C1046.4 (4)
C7—Fe—C1—C280.46 (18)C2—Fe—C6—C774.6 (2)
C9—Fe—C1—C2164.3 (3)C1—Fe—C6—C7117.48 (17)
C10—Fe—C1—C2163.81 (16)C9—Fe—C6—C781.82 (18)
C3—Fe—C1—C237.96 (15)C10—Fe—C6—C7119.7 (2)
C8—Fe—C1—C247.6 (3)C3—Fe—C6—C740.2 (4)
C5—Fe—C1—C2118.3 (2)C8—Fe—C6—C738.01 (18)
C4—Fe—C1—C281.58 (17)C5—Fe—C6—C7160.10 (17)
C2—Fe—C1—C11127.1 (3)C4—Fe—C6—C7166.1 (3)
C6—Fe—C1—C114.4 (3)C10—C6—C7—C80.1 (3)
C7—Fe—C1—C1146.7 (3)Fe—C6—C7—C859.62 (18)
C9—Fe—C1—C1168.6 (5)C10—C6—C7—Fe59.6 (2)
C10—Fe—C1—C1136.7 (3)C2—Fe—C7—C6123.91 (18)
C3—Fe—C1—C11165.1 (3)C1—Fe—C7—C680.5 (2)
C8—Fe—C1—C1179.5 (4)C9—Fe—C7—C681.29 (18)
C5—Fe—C1—C11114.5 (3)C10—Fe—C7—C637.27 (18)
C4—Fe—C1—C11151.3 (3)C3—Fe—C7—C6165.61 (17)
C5—C1—C2—C30.2 (3)C8—Fe—C7—C6118.8 (2)
C11—C1—C2—C3178.5 (3)C5—Fe—C7—C647.7 (4)
Fe—C1—C2—C360.37 (18)C4—Fe—C7—C6162.9 (4)
C5—C1—C2—C12175.8 (2)C2—Fe—C7—C8117.26 (17)
C11—C1—C2—C122.5 (4)C1—Fe—C7—C8160.65 (16)
Fe—C1—C2—C12115.6 (3)C6—Fe—C7—C8118.8 (2)
C5—C1—C2—Fe60.2 (2)C9—Fe—C7—C837.55 (17)
C11—C1—C2—Fe118.1 (3)C10—Fe—C7—C881.56 (18)
C1—Fe—C2—C3118.9 (2)C3—Fe—C7—C875.6 (2)
C6—Fe—C2—C3164.15 (16)C5—Fe—C7—C8166.5 (3)
C7—Fe—C2—C3123.27 (16)C4—Fe—C7—C844.0 (5)
C9—Fe—C2—C349.0 (3)C6—C7—C8—C90.3 (3)
C10—Fe—C2—C3165.6 (3)Fe—C7—C8—C959.20 (19)
C8—Fe—C2—C381.07 (19)C6—C7—C8—Fe59.47 (18)
C5—Fe—C2—C380.67 (17)C2—Fe—C8—C9160.35 (17)
C4—Fe—C2—C337.47 (16)C1—Fe—C8—C9164.9 (2)
C6—Fe—C2—C176.99 (18)C6—Fe—C8—C981.49 (19)
C7—Fe—C2—C1117.86 (16)C7—Fe—C8—C9119.3 (2)
C9—Fe—C2—C1167.8 (3)C10—Fe—C8—C937.88 (18)
C10—Fe—C2—C146.7 (4)C3—Fe—C8—C9117.53 (18)
C3—Fe—C2—C1118.9 (2)C5—Fe—C8—C944.4 (4)
C8—Fe—C2—C1160.07 (15)C4—Fe—C8—C976.4 (2)
C5—Fe—C2—C138.20 (16)C2—Fe—C8—C780.32 (19)
C4—Fe—C2—C181.40 (17)C1—Fe—C8—C745.5 (3)
C1—Fe—C2—C12122.6 (3)C6—Fe—C8—C737.84 (18)
C6—Fe—C2—C1245.7 (3)C9—Fe—C8—C7119.3 (2)
C7—Fe—C2—C124.8 (2)C10—Fe—C8—C781.45 (19)
C9—Fe—C2—C1269.5 (4)C3—Fe—C8—C7123.14 (18)
C10—Fe—C2—C1275.9 (4)C5—Fe—C8—C7163.8 (3)
C3—Fe—C2—C12118.5 (3)C4—Fe—C8—C7164.27 (18)
C8—Fe—C2—C1237.4 (3)C7—C8—C9—C100.4 (3)
C5—Fe—C2—C12160.8 (2)Fe—C8—C9—C1059.5 (2)
C4—Fe—C2—C12156.0 (2)C7—C8—C9—Fe59.09 (18)
C1—C2—C3—C40.3 (3)C2—Fe—C9—C844.9 (4)
C12—C2—C3—C4175.9 (2)C1—Fe—C9—C8161.1 (3)
Fe—C2—C3—C459.4 (2)C6—Fe—C9—C881.56 (19)
C1—C2—C3—Fe59.68 (18)C7—Fe—C9—C837.74 (18)
C12—C2—C3—Fe116.5 (2)C10—Fe—C9—C8119.1 (3)
C2—Fe—C3—C4119.4 (2)C3—Fe—C9—C880.2 (2)
C1—Fe—C3—C480.86 (18)C5—Fe—C9—C8163.91 (17)
C6—Fe—C3—C4164.5 (3)C4—Fe—C9—C8122.76 (18)
C7—Fe—C3—C4165.06 (17)C2—Fe—C9—C10164.0 (3)
C9—Fe—C3—C481.7 (2)C1—Fe—C9—C1042.0 (5)
C10—Fe—C3—C449.3 (3)C6—Fe—C9—C1037.52 (19)
C8—Fe—C3—C4123.70 (18)C7—Fe—C9—C1081.3 (2)
C5—Fe—C3—C436.72 (17)C3—Fe—C9—C10160.76 (18)
C1—Fe—C3—C238.58 (15)C8—Fe—C9—C10119.1 (3)
C6—Fe—C3—C245.0 (4)C5—Fe—C9—C1077.0 (2)
C7—Fe—C3—C275.51 (19)C4—Fe—C9—C10118.2 (2)
C9—Fe—C3—C2158.89 (16)C7—C6—C10—C90.2 (3)
C10—Fe—C3—C2168.7 (3)Fe—C6—C10—C959.3 (2)
C8—Fe—C3—C2116.87 (17)C7—C6—C10—Fe59.43 (19)
C5—Fe—C3—C282.71 (17)C8—C9—C10—C60.3 (3)
C4—Fe—C3—C2119.4 (2)Fe—C9—C10—C659.2 (2)
C2—C3—C4—C50.3 (3)C8—C9—C10—Fe59.6 (2)
Fe—C3—C4—C558.4 (2)C2—Fe—C10—C639.9 (4)
C2—C3—C4—Fe58.09 (18)C1—Fe—C10—C675.9 (2)
C2—Fe—C4—C582.6 (2)C7—Fe—C10—C637.46 (17)
C1—Fe—C4—C537.52 (18)C9—Fe—C10—C6119.2 (3)
C6—Fe—C4—C547.0 (4)C3—Fe—C10—C6164.2 (2)
C7—Fe—C4—C5162.1 (3)C8—Fe—C10—C681.48 (19)
C9—Fe—C4—C5122.95 (19)C5—Fe—C10—C6118.37 (18)
C10—Fe—C4—C580.4 (2)C4—Fe—C10—C6160.41 (17)
C3—Fe—C4—C5120.5 (3)C2—Fe—C10—C9159.1 (3)
C8—Fe—C4—C5164.51 (18)C1—Fe—C10—C9164.96 (18)
C2—Fe—C4—C337.92 (16)C6—Fe—C10—C9119.2 (3)
C1—Fe—C4—C382.97 (18)C7—Fe—C10—C981.71 (19)
C6—Fe—C4—C3167.5 (3)C3—Fe—C10—C945.0 (4)
C7—Fe—C4—C341.6 (5)C8—Fe—C10—C937.68 (19)
C9—Fe—C4—C3116.55 (18)C5—Fe—C10—C9122.5 (2)
C10—Fe—C4—C3159.08 (16)C4—Fe—C10—C980.4 (2)
C8—Fe—C4—C375.0 (2)C5—C1—C11—O11.1 (4)
C5—Fe—C4—C3120.5 (3)C2—C1—C11—O1177.0 (3)
C3—C4—C5—C10.2 (3)Fe—C1—C11—O185.4 (3)
Fe—C4—C5—C157.9 (2)C5—C1—C11—O2178.3 (3)
C3—C4—C5—Fe58.1 (2)C2—C1—C11—O23.6 (4)
C2—C1—C5—C40.0 (3)Fe—C1—C11—O295.2 (3)
C11—C1—C5—C4178.5 (2)C13—N—C12—O31.9 (3)
Fe—C1—C5—C459.0 (2)C13—N—C12—C2176.9 (2)
C2—C1—C5—Fe59.03 (18)C14—O3—C12—N6.8 (3)
C11—C1—C5—Fe119.5 (2)C14—O3—C12—C2174.3 (2)
C2—Fe—C5—C481.4 (2)C3—C2—C12—N177.6 (3)
C1—Fe—C5—C4120.3 (3)C1—C2—C12—N7.0 (4)
C6—Fe—C5—C4160.15 (18)Fe—C2—C12—N95.1 (3)
C7—Fe—C5—C4165.3 (3)C3—C2—C12—O31.2 (3)
C9—Fe—C5—C476.0 (2)C1—C2—C12—O3174.2 (2)
C10—Fe—C5—C4118.0 (2)Fe—C2—C12—O386.1 (2)
C3—Fe—C5—C437.10 (19)C12—N—C13—C15140.0 (3)
C8—Fe—C5—C442.5 (4)C12—N—C13—C149.3 (3)
C2—Fe—C5—C138.89 (16)C12—O3—C14—C1311.8 (3)
C6—Fe—C5—C179.6 (2)N—C13—C14—O312.6 (3)
C7—Fe—C5—C145.1 (4)C15—C13—C14—O3137.7 (3)
C9—Fe—C5—C1163.72 (16)N—C13—C15—C1655.0 (4)
C10—Fe—C5—C1121.74 (18)C14—C13—C15—C1665.8 (4)
C3—Fe—C5—C183.15 (18)N—C13—C15—C17176.3 (4)
C8—Fe—C5—C1162.7 (3)C14—C13—C15—C1755.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H90···N0.98 (7)1.61 (6)2.558 (3)161 (6)
C3—H3···O3i0.932.543.427 (3)160
C8—H8···Ni0.932.583.470 (3)159
Symmetry code: (i) y1, x+1, z+1/4.
 

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