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The title compound, [Fe2(C23H32B2N6O)2]·2C4H8O, features a dinuclear complex located on a centre of inversion. It crystallizes with two mol­ecules of tetra­hydro­furan in the asymmetric unit. The mol­ecular conformation of a pseudo­polymorph of the title complex with two mol­ecules of toluene in the asymmetric unit is almost identical. It is noteworthy that the hydroxyl H atom is shielded from any classical hydrogen-bond acceptor and there is only a short contact to the centre of an aromatic ring (centroid...H = 2.48 Å).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043346/at2388sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043346/at2388Isup2.hkl
Contains datablock I

CCDC reference: 664186

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.062
  • wR factor = 0.155
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT411_ALERT_2_B Short Inter H...H Contact H15 .. H52A .. 2.07 Ang. PLAT411_ALERT_2_B Short Inter H...H Contact H34 .. H53B .. 2.09 Ang. PLAT420_ALERT_2_B D-H Without Acceptor O1 - H1 ... ?
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 200 Ang. PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 - N31 .. 5.25 su PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O51 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C53 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C54 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C52 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C55 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10 PLAT731_ALERT_1_C Bond Calc 1.49(3), Rep 1.485(9) ...... 3.33 su-Ra C52 -C53 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 1.49(3), Rep 1.491(10) ...... 3.00 su-Ra C53 -C54 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 1.47(2), Rep 1.472(9) ...... 2.22 su-Ra C54 -C55 1.555 1.555
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1 (9) 2.32 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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

Comment top

Careful hydrolysis of the homoditopic phenylene-bridged Li and K scorpionates [m-(pz2BtBu)2C6H4]2- leads to the corresponding heteroditopic derivative [m-(pz(HO)BtBu)(pz2BtBu)C6H4]2-. We report here the X-ray crystal structure analysis of the macrocyclic complex (I). Very recently we have described the synthesis of the metallomacrocycle (I) (Zhang et al., 2007). X-ray quality crystals of the macrocycle (I) were grown from a tetrahydrofuran solution at ambient temperature.

Now we present a pseudopolymorph of this complex crystallized from tetrahydrofuran (Fig. 1). Both structures feature dinuclear complexes located on a centre of inversion. The title complex crystallizes with two molecules of tetrahydrofuran in the unit cell. It is noteworthy, that the hydroxyl H atom is shielded from any classical hydrogen bond acceptor. There is just a short contact to the centre of an aromatic ring [O1—H1 0.72 (5) Å, H1···cog(C41i—C46i) 2.48 Å, O1—H1···cog 132.4°; symmetry operator (i): 1 - x, 1 - y, 1 - z]. A least-squares of the complexes of the two pseudopolymorphs fitting all non-H atoms (r.m.s. deviation 0.091 Å) (Fig. 2) shows that the molecular conformations are almost identical. Thus, the solvent molecules in both crystal structures have no influence on the conformation of the complex.

Related literature top

For a related compound and synthesis, see: Zhang et al. (2007). Please provide figure 1; current figure 1 is same as figure 2.

Experimental top

The title compound (I) was synthesized according to the method described by Zhang et al. (2007). X-ray quality crystals of (I) (0.2 mmol) were grown from a tetrahydrofuran solution (10 ml) at ambient temperature.

Refinement top

H atoms were geometrically positioned and refined using a riding model with fixed individual displacement parameters [Uiso(H) = 1.2 Ueq(C,O) or Uiso(H) = 1.5 Ueq(Cmethyl)] and C—H ranging from 0.95Å to 0.99 Å. The coordinates of the hydroxyl H atom were refined. The C—C distance of the the molecules were refined with a distance restraint of 1.50 (1) Å.

Structure description top

Careful hydrolysis of the homoditopic phenylene-bridged Li and K scorpionates [m-(pz2BtBu)2C6H4]2- leads to the corresponding heteroditopic derivative [m-(pz(HO)BtBu)(pz2BtBu)C6H4]2-. We report here the X-ray crystal structure analysis of the macrocyclic complex (I). Very recently we have described the synthesis of the metallomacrocycle (I) (Zhang et al., 2007). X-ray quality crystals of the macrocycle (I) were grown from a tetrahydrofuran solution at ambient temperature.

Now we present a pseudopolymorph of this complex crystallized from tetrahydrofuran (Fig. 1). Both structures feature dinuclear complexes located on a centre of inversion. The title complex crystallizes with two molecules of tetrahydrofuran in the unit cell. It is noteworthy, that the hydroxyl H atom is shielded from any classical hydrogen bond acceptor. There is just a short contact to the centre of an aromatic ring [O1—H1 0.72 (5) Å, H1···cog(C41i—C46i) 2.48 Å, O1—H1···cog 132.4°; symmetry operator (i): 1 - x, 1 - y, 1 - z]. A least-squares of the complexes of the two pseudopolymorphs fitting all non-H atoms (r.m.s. deviation 0.091 Å) (Fig. 2) shows that the molecular conformations are almost identical. Thus, the solvent molecules in both crystal structures have no influence on the conformation of the complex.

For a related compound and synthesis, see: Zhang et al. (2007). Please provide figure 1; current figure 1 is same as figure 2.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. H atoms bonded to C and the solvent molecules omitted for clarity. Symmetry operator for generating equivalent atoms: -x + 1, -y + 1, -z + 1.
[Figure 2] Fig. 2. Least-squares fit of the title complex (open bonds) with its pseudopolymorph crystallized with toluene (full bonds).
(I) top
Crystal data top
[Fe2(C23H32B2N6O)2]·2C4H8OZ = 1
Mr = 1116.24F(000) = 592
Triclinic, P1Dx = 1.273 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.645 (2) ÅCell parameters from 10281 reflections
b = 12.363 (2) Åθ = 3.4–25.8°
c = 12.507 (2) ŵ = 0.55 mm1
α = 71.619 (12)°T = 173 K
β = 63.139 (12)°Block, colourless
γ = 66.862 (13)°0.32 × 0.24 × 0.13 mm
V = 1456.1 (5) Å3
Data collection top
STOE IPDS II two-circle
diffractometer
5438 independent reflections
Radiation source: fine-focus sealed tube3411 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
ω scansθmax = 25.7°, θmin = 3.5°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1414
Tmin = 0.843, Tmax = 0.932k = 1415
12022 measured reflectionsl = 1515
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 0.89 w = 1/[σ2(Fo2) + (0.0841P)2]
where P = (Fo2 + 2Fc2)/3
5438 reflections(Δ/σ)max = 0.006
346 parametersΔρmax = 0.71 e Å3
3 restraintsΔρmin = 0.48 e Å3
Crystal data top
[Fe2(C23H32B2N6O)2]·2C4H8Oγ = 66.862 (13)°
Mr = 1116.24V = 1456.1 (5) Å3
Triclinic, P1Z = 1
a = 11.645 (2) ÅMo Kα radiation
b = 12.363 (2) ŵ = 0.55 mm1
c = 12.507 (2) ÅT = 173 K
α = 71.619 (12)°0.32 × 0.24 × 0.13 mm
β = 63.139 (12)°
Data collection top
STOE IPDS II two-circle
diffractometer
5438 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
3411 reflections with I > 2σ(I)
Tmin = 0.843, Tmax = 0.932Rint = 0.079
12022 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0633 restraints
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 0.89Δρmax = 0.71 e Å3
5438 reflectionsΔρmin = 0.48 e Å3
346 parameters
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
Fe10.67506 (6)0.23657 (5)0.43545 (5)0.03806 (19)
B10.6272 (4)0.6466 (4)0.4266 (4)0.0347 (9)
C10.7258 (4)0.6458 (4)0.4873 (4)0.0446 (10)
C160.6609 (5)0.7524 (5)0.5551 (5)0.0614 (13)
H16A0.64510.82690.49820.092*
H16B0.72150.75250.58980.092*
H16C0.57500.74580.62060.092*
C170.8641 (5)0.6558 (4)0.3918 (5)0.0584 (12)
H17A0.85170.72780.33110.088*
H17B0.91150.58540.35170.088*
H17C0.91720.66060.43160.088*
C180.7467 (5)0.5330 (4)0.5815 (4)0.0534 (11)
H18A0.78840.46250.54210.080*
H18B0.65940.52890.64610.080*
H18C0.80550.53540.61670.080*
O10.4944 (3)0.6315 (2)0.5255 (3)0.0378 (6)
H10.486 (5)0.577 (4)0.568 (4)0.045*
B20.9482 (4)0.2460 (4)0.2463 (4)0.0372 (10)
C21.0880 (4)0.2689 (4)0.1373 (4)0.0451 (10)
C261.2155 (4)0.1607 (4)0.1204 (5)0.0588 (12)
H26A1.20040.09550.10500.088*
H26B1.23580.13460.19420.088*
H26C1.29160.18330.05120.088*
C271.0681 (5)0.3157 (4)0.0148 (4)0.0559 (12)
H27A1.05000.25500.00510.084*
H27B1.14980.33330.04950.084*
H27C0.99170.38860.02130.084*
C281.1163 (5)0.3695 (4)0.1599 (5)0.0547 (11)
H28A1.03630.43940.17160.082*
H28B1.19240.39090.08980.082*
H28C1.13820.34230.23290.082*
N110.8418 (3)0.1957 (3)0.4743 (3)0.0384 (7)
N120.9571 (3)0.2016 (3)0.3765 (3)0.0363 (7)
C131.0580 (4)0.1641 (4)0.4176 (4)0.0451 (10)
H131.14920.16070.36760.054*
C141.0105 (5)0.1319 (4)0.5403 (4)0.0510 (11)
H141.05970.10200.59210.061*
C150.8726 (5)0.1526 (4)0.5735 (4)0.0472 (10)
H150.81040.13840.65420.057*
N210.7824 (3)0.1335 (3)0.3015 (3)0.0377 (7)
N220.9084 (3)0.1441 (3)0.2278 (3)0.0374 (7)
C230.9705 (5)0.0626 (4)0.1544 (4)0.0466 (10)
H231.05940.05070.09460.056*
C240.8853 (5)0.0011 (4)0.1795 (4)0.0496 (11)
H240.90260.06420.14130.060*
C250.7695 (5)0.0458 (4)0.2716 (4)0.0456 (10)
H250.69150.01950.30860.055*
N310.5511 (3)0.1507 (3)0.5870 (3)0.0409 (8)
N320.4261 (3)0.2227 (3)0.6412 (3)0.0357 (7)
C330.3659 (5)0.1651 (4)0.7500 (4)0.0456 (10)
H330.27770.19660.80570.055*
C340.4508 (5)0.0533 (4)0.7695 (4)0.0548 (11)
H340.43460.00740.83880.066*
C350.5645 (5)0.0494 (4)0.6655 (4)0.0512 (11)
H350.64310.01740.65130.061*
C410.8185 (4)0.3640 (3)0.2563 (3)0.0344 (8)
C420.7845 (4)0.4487 (3)0.3267 (3)0.0337 (8)
H420.83670.43230.37350.040*
C430.6796 (3)0.5553 (3)0.3330 (3)0.0328 (8)
C440.6057 (4)0.5772 (3)0.2612 (4)0.0368 (8)
H440.53300.64840.26270.044*
C450.6361 (4)0.4975 (4)0.1885 (4)0.0394 (9)
H450.58510.51510.14030.047*
C460.7406 (4)0.3923 (4)0.1858 (3)0.0382 (9)
H460.76020.33830.13580.046*
O510.2229 (15)0.7421 (11)0.1334 (15)0.305 (8)
C520.2894 (18)0.8316 (14)0.0926 (15)0.203 (7)
H52A0.28830.85530.16170.244*
H52B0.24810.90310.04360.244*
C530.4281 (17)0.7680 (13)0.0174 (15)0.332 (19)
H53A0.48750.73640.06410.399*
H53B0.46650.82250.05660.399*
C540.4151 (11)0.6687 (18)0.0155 (10)0.273 (14)
H54A0.39750.69600.09150.327*
H54B0.49910.60110.02770.327*
C550.3015 (14)0.6316 (10)0.0861 (10)0.158 (5)
H55A0.33150.56680.14710.189*
H55B0.25110.60590.05760.189*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0325 (3)0.0385 (3)0.0401 (3)0.0055 (2)0.0123 (2)0.0112 (3)
B10.030 (2)0.031 (2)0.036 (2)0.0068 (17)0.0083 (17)0.0065 (18)
C10.043 (2)0.041 (2)0.055 (3)0.0087 (18)0.023 (2)0.012 (2)
C160.065 (3)0.057 (3)0.079 (3)0.005 (2)0.041 (3)0.028 (3)
C170.045 (2)0.054 (3)0.083 (3)0.015 (2)0.025 (2)0.017 (3)
C180.061 (3)0.050 (3)0.056 (3)0.007 (2)0.035 (2)0.009 (2)
O10.0384 (14)0.0317 (15)0.0375 (16)0.0121 (12)0.0104 (12)0.0022 (12)
B20.039 (2)0.033 (2)0.038 (2)0.0060 (18)0.0158 (19)0.0088 (19)
C20.041 (2)0.038 (2)0.046 (2)0.0076 (17)0.0095 (18)0.0093 (19)
C260.039 (2)0.055 (3)0.068 (3)0.006 (2)0.008 (2)0.022 (2)
C270.055 (3)0.055 (3)0.042 (2)0.016 (2)0.006 (2)0.006 (2)
C280.046 (2)0.052 (3)0.062 (3)0.019 (2)0.012 (2)0.010 (2)
N110.0416 (17)0.0377 (18)0.0355 (18)0.0098 (14)0.0173 (15)0.0038 (14)
N120.0354 (16)0.0326 (16)0.0384 (18)0.0056 (13)0.0151 (14)0.0067 (14)
C130.041 (2)0.042 (2)0.058 (3)0.0080 (18)0.027 (2)0.008 (2)
C140.056 (3)0.046 (2)0.061 (3)0.009 (2)0.039 (2)0.004 (2)
C150.058 (3)0.040 (2)0.044 (2)0.012 (2)0.024 (2)0.0037 (19)
N210.0368 (16)0.0390 (18)0.0372 (17)0.0112 (14)0.0125 (14)0.0085 (14)
N220.0375 (17)0.0334 (17)0.0361 (17)0.0052 (13)0.0123 (14)0.0083 (14)
C230.055 (2)0.039 (2)0.042 (2)0.0086 (19)0.015 (2)0.0126 (19)
C240.067 (3)0.039 (2)0.051 (3)0.015 (2)0.025 (2)0.016 (2)
C250.053 (2)0.042 (2)0.049 (2)0.0166 (19)0.025 (2)0.005 (2)
N310.0376 (17)0.0328 (17)0.051 (2)0.0016 (14)0.0199 (15)0.0112 (16)
N320.0355 (16)0.0327 (17)0.0368 (18)0.0100 (14)0.0108 (14)0.0074 (14)
C330.052 (2)0.042 (2)0.042 (2)0.0207 (19)0.0134 (19)0.0037 (19)
C340.070 (3)0.041 (2)0.054 (3)0.019 (2)0.031 (2)0.007 (2)
C350.055 (3)0.030 (2)0.063 (3)0.0039 (19)0.028 (2)0.004 (2)
C410.0351 (19)0.034 (2)0.0326 (19)0.0124 (16)0.0110 (16)0.0041 (16)
C420.0333 (18)0.0298 (19)0.038 (2)0.0080 (15)0.0138 (16)0.0072 (16)
C430.0302 (18)0.0296 (18)0.0341 (19)0.0093 (14)0.0091 (15)0.0034 (16)
C440.0361 (19)0.0302 (19)0.041 (2)0.0052 (15)0.0169 (17)0.0036 (17)
C450.043 (2)0.040 (2)0.037 (2)0.0107 (17)0.0211 (17)0.0025 (17)
C460.044 (2)0.039 (2)0.0308 (19)0.0134 (17)0.0128 (17)0.0057 (17)
O510.276 (14)0.186 (10)0.390 (19)0.067 (10)0.006 (13)0.154 (12)
C520.28 (2)0.162 (12)0.262 (18)0.106 (14)0.177 (17)0.019 (12)
C530.173 (14)0.34 (3)0.35 (3)0.134 (17)0.159 (18)0.27 (2)
C540.086 (7)0.60 (4)0.111 (8)0.005 (13)0.031 (6)0.185 (16)
C550.229 (14)0.142 (9)0.146 (9)0.029 (9)0.132 (10)0.020 (7)
Geometric parameters (Å, º) top
Fe1—O1i1.973 (3)C14—C151.399 (6)
Fe1—N112.046 (3)C14—H140.9500
Fe1—N212.048 (3)C15—H150.9500
Fe1—N312.065 (4)N21—C251.331 (5)
B1—O11.520 (5)N21—N221.369 (5)
B1—N32i1.593 (5)N22—C231.339 (5)
B1—C431.632 (5)C23—C241.371 (7)
B1—C11.633 (6)C23—H230.9500
C1—C181.533 (6)C24—C251.372 (6)
C1—C171.536 (7)C24—H240.9500
C1—C161.540 (6)C25—H250.9500
C16—H16A0.9800N31—C351.329 (6)
C16—H16B0.9800N31—N321.357 (4)
C16—H16C0.9800N32—C331.330 (5)
C17—H17A0.9800N32—B1i1.593 (5)
C17—H17B0.9800C33—C341.370 (6)
C17—H17C0.9800C33—H330.9500
C18—H18A0.9800C34—C351.371 (7)
C18—H18B0.9800C34—H340.9500
C18—H18C0.9800C35—H350.9500
O1—Fe1i1.973 (3)C41—C421.404 (5)
O1—H10.72 (5)C41—C461.415 (5)
B2—N121.584 (5)C42—C431.396 (5)
B2—N221.610 (5)C42—H420.9500
B2—C411.625 (5)C43—C441.408 (5)
B2—C21.644 (6)C44—C451.387 (5)
C2—C281.537 (6)C44—H440.9500
C2—C261.540 (6)C45—C461.386 (5)
C2—C271.547 (6)C45—H450.9500
C26—H26A0.9800C46—H460.9500
C26—H26B0.9800O51—C551.447 (13)
C26—H26C0.9800O51—C521.429 (17)
C27—H27A0.9800C52—C531.485 (9)
C27—H27B0.9800C52—H52A0.9900
C27—H27C0.9800C52—H52B0.9900
C28—H28A0.9800C53—C541.491 (10)
C28—H28B0.9800C53—H53A0.9900
C28—H28C0.9800C53—H53B0.9900
N11—C151.337 (5)C54—C551.472 (9)
N11—N121.357 (5)C54—H54A0.9900
N12—C131.351 (5)C54—H54B0.9900
C13—C141.357 (7)C55—H55A0.9900
C13—H130.9500C55—H55B0.9900
O1i—Fe1—N11130.37 (12)C13—C14—H14127.8
O1i—Fe1—N21135.07 (12)C15—C14—H14127.8
N11—Fe1—N2191.19 (13)N11—C15—C14109.6 (4)
O1i—Fe1—N3179.47 (12)N11—C15—H15125.2
N11—Fe1—N31103.53 (13)C14—C15—H15125.2
N21—Fe1—N31110.22 (13)C25—N21—N22107.1 (3)
O1—B1—N32i99.5 (3)C25—N21—Fe1136.8 (3)
O1—B1—C43107.7 (3)N22—N21—Fe1115.6 (2)
N32i—B1—C43106.7 (3)C23—N22—N21108.3 (3)
O1—B1—C1110.0 (3)C23—N22—B2135.1 (4)
N32i—B1—C1110.4 (3)N21—N22—B2116.6 (3)
C43—B1—C1120.5 (3)N22—C23—C24109.1 (4)
C18—C1—C17108.9 (4)N22—C23—H23125.5
C18—C1—C16106.6 (4)C24—C23—H23125.5
C17—C1—C16107.4 (4)C23—C24—C25105.3 (4)
C18—C1—B1111.4 (4)C23—C24—H24127.3
C17—C1—B1112.4 (4)C25—C24—H24127.3
C16—C1—B1109.9 (3)N21—C25—C24110.2 (4)
C1—C16—H16A109.5N21—C25—H25124.9
C1—C16—H16B109.5C24—C25—H25124.9
H16A—C16—H16B109.5C35—N31—N32105.9 (3)
C1—C16—H16C109.5C35—N31—Fe1137.6 (3)
H16A—C16—H16C109.5N32—N31—Fe1114.5 (2)
H16B—C16—H16C109.5C33—N32—N31109.1 (3)
C1—C17—H17A109.5C33—N32—B1i130.3 (3)
C1—C17—H17B109.5N31—N32—B1i120.6 (3)
H17A—C17—H17B109.5N32—C33—C34109.6 (4)
C1—C17—H17C109.5N32—C33—H33125.2
H17A—C17—H17C109.5C34—C33—H33125.2
H17B—C17—H17C109.5C33—C34—C35103.8 (4)
C1—C18—H18A109.5C33—C34—H34128.1
C1—C18—H18B109.5C35—C34—H34128.1
H18A—C18—H18B109.5N31—C35—C34111.6 (4)
C1—C18—H18C109.5N31—C35—H35124.2
H18A—C18—H18C109.5C34—C35—H35124.2
H18B—C18—H18C109.5C42—C41—C46116.2 (3)
B1—O1—Fe1i123.8 (2)C42—C41—B2122.1 (3)
B1—O1—H1125 (4)C46—C41—B2121.5 (3)
Fe1i—O1—H1111 (4)C43—C42—C41124.7 (3)
N12—B2—N22104.7 (3)C43—C42—H42117.6
N12—B2—C41106.8 (3)C41—C42—H42117.6
N22—B2—C41105.7 (3)C42—C43—C44116.0 (3)
N12—B2—C2113.3 (3)C42—C43—B1125.2 (3)
N22—B2—C2112.6 (3)C44—C43—B1118.5 (3)
C41—B2—C2113.0 (3)C45—C44—C43121.8 (3)
C28—C2—C26107.9 (4)C45—C44—H44119.1
C28—C2—C27105.5 (4)C43—C44—H44119.1
C26—C2—C27107.9 (4)C46—C45—C44120.3 (3)
C28—C2—B2109.2 (3)C46—C45—H45119.8
C26—C2—B2116.3 (4)C44—C45—H45119.8
C27—C2—B2109.5 (4)C45—C46—C41121.0 (3)
C2—C26—H26A109.5C45—C46—H46119.5
C2—C26—H26B109.5C41—C46—H46119.5
H26A—C26—H26B109.5C55—O51—C52116.5 (13)
C2—C26—H26C109.5O51—C52—C53101.5 (13)
H26A—C26—H26C109.5O51—C52—H52A111.5
H26B—C26—H26C109.5C53—C52—H52A111.5
C2—C27—H27A109.5O51—C52—H52B111.5
C2—C27—H27B109.5C53—C52—H52B111.5
H27A—C27—H27B109.5H52A—C52—H52B109.3
C2—C27—H27C109.5C52—C53—C54105.8 (13)
H27A—C27—H27C109.5C52—C53—H53A110.6
H27B—C27—H27C109.5C54—C53—H53A110.6
C2—C28—H28A109.5C52—C53—H53B110.6
C2—C28—H28B109.5C54—C53—H53B110.6
H28A—C28—H28B109.5H53A—C53—H53B108.7
C2—C28—H28C109.5C55—C54—C53106.8 (10)
H28A—C28—H28C109.5C55—C54—H54A110.4
H28B—C28—H28C109.5C53—C54—H54A110.4
C15—N11—N12107.8 (3)C55—C54—H54B110.4
C15—N11—Fe1136.3 (3)C53—C54—H54B110.4
N12—N11—Fe1115.5 (2)H54A—C54—H54B108.6
C13—N12—N11107.7 (3)C54—C55—O51100.1 (10)
C13—N12—B2134.6 (3)C54—C55—H55A111.8
N11—N12—B2117.7 (3)O51—C55—H55A111.8
N12—C13—C14110.4 (4)C54—C55—H55B111.8
N12—C13—H13124.8O51—C55—H55B111.8
C14—C13—H13124.8H55A—C55—H55B109.5
C13—C14—C15104.4 (4)
O1—B1—C1—C1855.2 (4)C41—B2—N22—C23134.9 (4)
N32i—B1—C1—C18164.1 (3)C2—B2—N22—C2311.0 (6)
C43—B1—C1—C1870.9 (5)N12—B2—N22—N2167.6 (4)
O1—B1—C1—C17177.7 (3)C41—B2—N22—N2145.0 (4)
N32i—B1—C1—C1773.4 (4)C2—B2—N22—N21168.9 (3)
C43—B1—C1—C1751.6 (5)N21—N22—C23—C240.3 (5)
O1—B1—C1—C1662.7 (5)B2—N22—C23—C24179.6 (4)
N32i—B1—C1—C1646.1 (5)N22—C23—C24—C250.3 (5)
C43—B1—C1—C16171.1 (4)N22—N21—C25—C240.0 (5)
N32i—B1—O1—Fe1i12.4 (4)Fe1—N21—C25—C24171.5 (3)
C43—B1—O1—Fe1i123.4 (3)C23—C24—C25—N210.1 (5)
C1—B1—O1—Fe1i103.5 (3)O1i—Fe1—N31—C35165.3 (4)
N12—B2—C2—C2863.1 (4)N11—Fe1—N31—C3536.0 (4)
N22—B2—C2—C28178.4 (3)N21—Fe1—N31—C3560.4 (4)
C41—B2—C2—C2858.6 (4)O1i—Fe1—N31—N324.4 (2)
N12—B2—C2—C2659.2 (5)N11—Fe1—N31—N32124.9 (2)
N22—B2—C2—C2659.3 (5)N21—Fe1—N31—N32138.7 (2)
C41—B2—C2—C26179.1 (4)C35—N31—N32—C330.2 (4)
N12—B2—C2—C27178.2 (3)Fe1—N31—N32—C33166.9 (3)
N22—B2—C2—C2763.3 (4)C35—N31—N32—B1i179.6 (3)
C41—B2—C2—C2756.5 (4)Fe1—N31—N32—B1i13.7 (4)
O1i—Fe1—N11—C1571.6 (4)N31—N32—C33—C340.0 (5)
N21—Fe1—N11—C15127.1 (4)B1i—N32—C33—C34179.3 (4)
N31—Fe1—N11—C1516.0 (4)N32—C33—C34—C350.3 (5)
O1i—Fe1—N11—N12116.0 (2)N32—N31—C35—C340.4 (5)
N21—Fe1—N11—N1245.2 (3)Fe1—N31—C35—C34162.3 (3)
N31—Fe1—N11—N12156.4 (2)C33—C34—C35—N310.4 (5)
C15—N11—N12—C131.2 (4)N12—B2—C41—C4237.8 (5)
Fe1—N11—N12—C13175.7 (3)N22—B2—C41—C42148.9 (4)
C15—N11—N12—B2177.9 (3)C2—B2—C41—C4287.5 (4)
Fe1—N11—N12—B23.4 (4)N12—B2—C41—C46147.9 (4)
N22—B2—N12—C13113.1 (5)N22—B2—C41—C4636.8 (5)
C41—B2—N12—C13135.0 (4)C2—B2—C41—C4686.8 (4)
C2—B2—N12—C139.9 (6)C46—C41—C42—C431.2 (6)
N22—B2—N12—N1165.7 (4)B2—C41—C42—C43175.8 (4)
C41—B2—N12—N1146.2 (4)C41—C42—C43—C440.7 (6)
C2—B2—N12—N11171.3 (3)C41—C42—C43—B1172.1 (4)
N11—N12—C13—C141.0 (4)O1—B1—C43—C42105.1 (4)
B2—N12—C13—C14177.9 (4)N32i—B1—C43—C42148.9 (4)
N12—C13—C14—C150.4 (5)C1—B1—C43—C4222.1 (6)
N12—N11—C15—C141.0 (5)O1—B1—C43—C4467.6 (4)
Fe1—N11—C15—C14173.8 (3)N32i—B1—C43—C4438.5 (4)
C13—C14—C15—N110.4 (5)C1—B1—C43—C44165.2 (4)
O1i—Fe1—N21—C2572.2 (4)C42—C43—C44—C450.3 (6)
N11—Fe1—N21—C25128.0 (4)B1—C43—C44—C45173.6 (4)
N31—Fe1—N21—C2523.2 (4)C43—C44—C45—C460.8 (6)
O1i—Fe1—N21—N22116.8 (3)C44—C45—C46—C410.3 (6)
N11—Fe1—N21—N2242.9 (3)C42—C41—C46—C450.7 (6)
N31—Fe1—N21—N22147.8 (2)B2—C41—C46—C45175.3 (4)
C25—N21—N22—C230.2 (4)C55—O51—C52—C534 (2)
Fe1—N21—N22—C23173.4 (3)O51—C52—C53—C5420.9 (17)
C25—N21—N22—B2179.7 (3)C52—C53—C54—C5531.5 (17)
Fe1—N21—N22—B26.7 (4)C53—C54—C55—O5127.2 (15)
N12—B2—N22—C23112.5 (5)C52—O51—C55—C5414.7 (17)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Fe2(C23H32B2N6O)2]·2C4H8O
Mr1116.24
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)11.645 (2), 12.363 (2), 12.507 (2)
α, β, γ (°)71.619 (12), 63.139 (12), 66.862 (13)
V3)1456.1 (5)
Z1
Radiation typeMo Kα
µ (mm1)0.55
Crystal size (mm)0.32 × 0.24 × 0.13
Data collection
DiffractometerSTOE IPDS II two-circle
diffractometer
Absorption correctionMulti-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin, Tmax0.843, 0.932
No. of measured, independent and
observed [I > 2σ(I)] reflections
12022, 5438, 3411
Rint0.079
(sin θ/λ)max1)0.611
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.155, 0.89
No. of reflections5438
No. of parameters346
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.71, 0.48

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

 

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