{6,6′-Dimeth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato}(ethanol)dioxouranium(VI)

In the title compound, [UO₂(C₁₈H₁₈N₂O₄)(C₂H₆O)], the U atom has a distorted penta­gonal–bipyramidal geometry with a tetra­dentate Schiff base and ethanol ligands in the equatorial plane and oxo atoms in the axial positions. Complex mol­ecules are connected by O—H...O and C—H...O inter­actions, forming dimers in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.042
• wR factor = 0.099
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found





Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.104
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         O5
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         16

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

{6,6'-Dimethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}- (ethanol)dioxouranium(VI)

Crystal data

[U(C18H18N2O4)O2(C2H6O)]	F(000) = 2448
Mr = 642.44	Dx = 1.984 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 65152 reflections
a = 9.2132 (4) Å	θ = 1.7–27.2°
b = 23.6595 (10) Å	µ = 7.60 mm^−1
c = 19.7075 (10) Å	T = 296 K
V = 4295.8 (3) Å^3	Plate, red
Z = 8	0.43 × 0.23 × 0.05 mm

Data collection

Stoe IPDS-2 diffractometer	4219 independent reflections
Radiation source: fine-focus sealed tube	2789 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.104
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.7°
ω scans	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −29→29
Tmin = 0.104, Tmax = 0.597	l = −24→24
57109 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0393P)^2 + 9.9627P] where P = (Fo^2 + 2Fc^2)/3
4219 reflections	(Δ/σ)max < 0.001
274 parameters	Δρmax = 1.26 e Å^−3
22 restraints	Δρmin = −0.68 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
U1	0.42021 (3)	0.421967 (14)	0.126908 (15)	0.04687 (11)
O1	0.3663 (7)	0.5146 (3)	0.1123 (3)	0.0593 (17)
O2	0.2410 (9)	0.5867 (3)	0.0290 (3)	0.077 (2)
O3	0.5862 (8)	0.2777 (3)	−0.0106 (4)	0.077 (2)
O4	0.4683 (7)	0.3336 (3)	0.0907 (3)	0.0580 (16)
O5	0.4521 (8)	0.4366 (3)	0.0037 (3)	0.0661 (19)
O6	0.6066 (7)	0.4376 (3)	0.1345 (3)	0.0617 (17)
O7	0.2355 (7)	0.4048 (3)	0.1230 (3)	0.0651 (17)
N1	0.3791 (7)	0.4687 (3)	0.2413 (4)	0.0477 (17)
N2	0.4615 (8)	0.3569 (3)	0.2278 (4)	0.0549 (19)
C1	0.2677 (10)	0.5490 (4)	0.1379 (4)	0.054 (2)
C2	0.2326 (10)	0.5493 (4)	0.2080 (4)	0.049 (2)
C3	0.1317 (12)	0.5883 (4)	0.2318 (5)	0.066 (3)
H3	0.1099	0.5882	0.2779	0.079*
C4	0.0641 (12)	0.6260 (5)	0.1919 (5)	0.073 (3)
H4	−0.0020	0.6517	0.2099	0.087*
C5	0.0965 (11)	0.6256 (4)	0.1214 (6)	0.070 (3)
H5	0.0493	0.6505	0.0922	0.084*
C6	0.1987 (10)	0.5881 (4)	0.0963 (4)	0.051 (2)
C7	0.3028 (9)	0.5117 (4)	0.2551 (5)	0.056 (2)
H7	0.2907	0.5200	0.3009	0.068*
C8	0.4471 (10)	0.4394 (4)	0.2984 (4)	0.055 (2)
H8A	0.4126	0.4553	0.3409	0.066*
H8B	0.5516	0.4441	0.2965	0.066*
C9	0.4092 (11)	0.3779 (4)	0.2947 (4)	0.060 (2)
H9A	0.4558	0.3574	0.3313	0.072*
H9B	0.3050	0.3729	0.2985	0.072*
C10	0.5405 (10)	0.3126 (5)	0.2280 (5)	0.063 (3)
H10	0.5570	0.2972	0.2707	0.075*
C11	0.6060 (10)	0.2837 (4)	0.1746 (6)	0.060 (3)
C12	0.7094 (13)	0.2427 (5)	0.1877 (7)	0.072 (3)
H12	0.7348	0.2342	0.2322	0.086*
C13	0.7750 (12)	0.2142 (4)	0.1347 (7)	0.078 (3)
H13	0.8455	0.1872	0.1442	0.094*
C14	0.7390 (13)	0.2247 (5)	0.0690 (7)	0.075 (3)
H14	0.7854	0.2052	0.0342	0.090*
C15	0.6345 (12)	0.2638 (5)	0.0541 (7)	0.068 (3)
C16	0.5661 (10)	0.2955 (4)	0.1048 (5)	0.054 (2)
C17	0.358 (2)	0.4244 (7)	−0.0511 (9)	0.135 (7)
H17A	0.3509	0.3838	−0.0566	0.162*
H17B	0.3981	0.4400	−0.0925	0.162*
C18	0.2101 (19)	0.4480 (9)	−0.0401 (9)	0.164 (9)
H18A	0.1493	0.4386	−0.0780	0.197*
H18B	0.2162	0.4884	−0.0358	0.197*
H18C	0.1694	0.4324	0.0006	0.197*
C19	0.1615 (12)	0.6191 (6)	−0.0171 (5)	0.077 (3)
H19A	0.2013	0.6145	−0.0618	0.115*
H19B	0.1665	0.6582	−0.0043	0.115*
H19C	0.0621	0.6070	−0.0169	0.115*
C20	0.6477 (16)	0.2479 (6)	−0.0691 (7)	0.105 (5)
H20A	0.6039	0.2619	−0.1100	0.157*
H20B	0.6289	0.2082	−0.0649	0.157*
H20C	0.7505	0.2543	−0.0707	0.157*
H5A	0.539 (5)	0.442 (7)	−0.004 (9)	0.157*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
U1	0.04451 (16)	0.05380 (19)	0.04231 (16)	0.00486 (17)	0.00274 (16)	−0.00073 (17)
O1	0.077 (4)	0.057 (4)	0.044 (4)	0.017 (3)	0.011 (3)	0.000 (3)
O2	0.089 (5)	0.082 (5)	0.058 (4)	0.028 (5)	0.013 (4)	0.014 (4)
O3	0.085 (5)	0.079 (5)	0.066 (4)	0.014 (5)	0.005 (4)	−0.024 (4)
O4	0.064 (4)	0.055 (4)	0.055 (4)	0.010 (3)	0.000 (3)	−0.006 (3)
O5	0.080 (5)	0.082 (5)	0.036 (3)	0.003 (4)	0.004 (3)	−0.005 (3)
O6	0.066 (4)	0.073 (4)	0.046 (3)	−0.005 (3)	0.002 (3)	0.001 (3)
O7	0.059 (3)	0.086 (5)	0.050 (3)	0.003 (3)	0.005 (3)	−0.013 (4)
N1	0.048 (4)	0.050 (4)	0.045 (4)	0.004 (3)	0.000 (3)	0.001 (3)
N2	0.056 (4)	0.053 (5)	0.056 (5)	−0.001 (4)	0.004 (4)	0.003 (4)
C1	0.055 (5)	0.053 (5)	0.054 (5)	−0.010 (5)	0.002 (4)	−0.006 (4)
C2	0.060 (5)	0.053 (5)	0.035 (4)	0.005 (5)	−0.002 (4)	−0.005 (4)
C3	0.078 (7)	0.065 (7)	0.054 (6)	0.014 (5)	0.004 (5)	−0.013 (5)
C4	0.078 (7)	0.081 (8)	0.059 (6)	0.027 (6)	0.009 (5)	0.001 (5)
C5	0.067 (6)	0.075 (7)	0.067 (6)	0.011 (5)	−0.006 (6)	0.007 (6)
C6	0.057 (5)	0.058 (6)	0.040 (4)	0.005 (4)	0.007 (4)	0.004 (4)
C7	0.056 (6)	0.062 (6)	0.052 (5)	−0.005 (5)	0.004 (4)	−0.005 (5)
C8	0.057 (6)	0.067 (6)	0.040 (4)	0.005 (4)	−0.002 (4)	0.000 (4)
C9	0.070 (6)	0.072 (7)	0.038 (4)	0.000 (6)	0.011 (5)	0.008 (4)
C10	0.059 (6)	0.067 (7)	0.063 (6)	−0.001 (5)	0.007 (5)	0.018 (5)
C11	0.050 (5)	0.046 (6)	0.084 (7)	0.009 (4)	0.000 (5)	0.002 (5)
C12	0.070 (8)	0.053 (7)	0.093 (9)	0.001 (5)	−0.004 (7)	0.011 (6)
C13	0.067 (6)	0.054 (6)	0.113 (10)	0.014 (5)	0.004 (7)	0.014 (7)
C14	0.068 (7)	0.054 (7)	0.104 (9)	0.007 (6)	0.003 (7)	−0.006 (6)
C15	0.059 (6)	0.046 (6)	0.098 (7)	−0.005 (6)	0.010 (6)	−0.011 (6)
C16	0.053 (5)	0.043 (5)	0.066 (6)	−0.006 (5)	0.012 (5)	0.002 (4)
C17	0.176 (17)	0.128 (15)	0.100 (11)	−0.077 (13)	−0.020 (12)	−0.013 (11)
C18	0.124 (14)	0.25 (2)	0.118 (13)	−0.066 (16)	−0.065 (12)	0.001 (14)
C19	0.081 (7)	0.100 (10)	0.050 (6)	0.003 (7)	−0.001 (5)	0.020 (6)
C20	0.112 (11)	0.120 (14)	0.083 (9)	0.023 (9)	0.010 (8)	−0.038 (8)

Geometric parameters (Å, º)

U1—O7	1.752 (7)	C7—H7	0.9300
U1—O6	1.763 (7)	C8—C9	1.498 (14)
U1—O4	2.253 (6)	C8—H8A	0.9700
U1—O1	2.265 (6)	C8—H8B	0.9700
U1—O5	2.471 (6)	C9—H9A	0.9700
U1—N1	2.540 (7)	C9—H9B	0.9700
U1—N2	2.542 (8)	C10—C11	1.394 (14)
O1—C1	1.320 (11)	C10—H10	0.9300
O2—C6	1.383 (10)	C11—C12	1.384 (14)
O2—C19	1.396 (12)	C11—C16	1.450 (14)
O3—C15	1.390 (14)	C12—C13	1.382 (16)
O3—C20	1.464 (13)	C12—H12	0.9300
O4—C16	1.305 (11)	C13—C14	1.359 (16)
O5—C17	1.415 (17)	C13—H13	0.9300
O5—H5A	0.83 (6)	C14—C15	1.367 (15)
N1—C7	1.267 (11)	C14—H14	0.9300
N1—C8	1.461 (11)	C15—C16	1.401 (14)
N2—C10	1.276 (12)	C17—C18	1.487 (16)
N2—C9	1.490 (11)	C17—H17A	0.9700
C1—C6	1.390 (13)	C17—H17B	0.9700
C1—C2	1.418 (11)	C18—H18A	0.9600
C2—C3	1.392 (13)	C18—H18B	0.9600
C2—C7	1.438 (13)	C18—H18C	0.9600
C3—C4	1.343 (14)	C19—H19A	0.9600
C3—H3	0.9300	C19—H19B	0.9600
C4—C5	1.421 (14)	C19—H19C	0.9600
C4—H4	0.9300	C20—H20A	0.9600
C5—C6	1.386 (13)	C20—H20B	0.9600
C5—H5	0.9300	C20—H20C	0.9600
O7—U1—O6	177.3 (3)	N1—C8—H8A	109.9
O7—U1—O4	87.8 (3)	C9—C8—H8A	109.9
O6—U1—O4	91.7 (3)	N1—C8—H8B	109.9
O7—U1—O1	90.3 (3)	C9—C8—H8B	109.9
O6—U1—O1	91.3 (3)	H8A—C8—H8B	108.3
O4—U1—O1	154.2 (2)	N2—C9—C8	107.0 (7)
O7—U1—O5	96.1 (3)	N2—C9—H9A	110.3
O6—U1—O5	86.5 (3)	C8—C9—H9A	110.3
O4—U1—O5	78.2 (2)	N2—C9—H9B	110.3
O1—U1—O5	76.4 (2)	C8—C9—H9B	110.3
O7—U1—N1	89.7 (3)	H9A—C9—H9B	108.6
O6—U1—N1	88.8 (3)	N2—C10—C11	130.4 (10)
O4—U1—N1	135.6 (2)	N2—C10—H10	114.8
O1—U1—N1	70.1 (2)	C11—C10—H10	114.8
O5—U1—N1	146.0 (2)	C12—C11—C10	120.1 (11)
O7—U1—N2	92.2 (3)	C12—C11—C16	119.2 (10)
O6—U1—N2	85.1 (3)	C10—C11—C16	120.7 (8)
O4—U1—N2	69.9 (2)	C11—C12—C13	120.1 (12)
O1—U1—N2	135.9 (2)	C11—C12—H12	120.0
O5—U1—N2	146.7 (3)	C13—C12—H12	120.0
N1—U1—N2	65.9 (2)	C14—C13—C12	121.6 (11)
C1—O1—U1	134.3 (6)	C14—C13—H13	119.2
C6—O2—C19	117.6 (8)	C12—C13—H13	119.2
C15—O3—C20	118.9 (9)	C13—C14—C15	120.0 (11)
C16—O4—U1	135.2 (6)	C13—C14—H14	120.0
C17—O5—U1	130.4 (8)	C15—C14—H14	120.0
C17—O5—H5A	119 (10)	C14—C15—O3	125.7 (11)
U1—O5—H5A	109 (10)	C14—C15—C16	121.7 (12)
C7—N1—C8	117.0 (8)	O3—C15—C16	112.6 (10)
C7—N1—U1	128.5 (6)	O4—C16—C15	121.9 (10)
C8—N1—U1	114.4 (5)	O4—C16—C11	120.8 (8)
C10—N2—C9	117.1 (8)	C15—C16—C11	117.3 (9)
C10—N2—U1	125.8 (7)	O5—C17—C18	112.0 (13)
C9—N2—U1	116.2 (6)	O5—C17—H17A	109.2
O1—C1—C6	120.0 (8)	C18—C17—H17A	109.2
O1—C1—C2	122.2 (9)	O5—C17—H17B	109.2
C6—C1—C2	117.8 (8)	C18—C17—H17B	109.2
C3—C2—C1	119.0 (9)	H17A—C17—H17B	107.9
C3—C2—C7	119.4 (8)	C17—C18—H18A	109.5
C1—C2—C7	121.5 (8)	C17—C18—H18B	109.5
C4—C3—C2	123.5 (9)	H18A—C18—H18B	109.5
C4—C3—H3	118.2	C17—C18—H18C	109.5
C2—C3—H3	118.2	H18A—C18—H18C	109.5
C3—C4—C5	118.1 (10)	H18B—C18—H18C	109.5
C3—C4—H4	120.9	O2—C19—H19A	109.5
C5—C4—H4	120.9	O2—C19—H19B	109.5
C6—C5—C4	119.7 (9)	H19A—C19—H19B	109.5
C6—C5—H5	120.2	O2—C19—H19C	109.5
C4—C5—H5	120.2	H19A—C19—H19C	109.5
O2—C6—C5	123.3 (9)	H19B—C19—H19C	109.5
O2—C6—C1	114.9 (8)	O3—C20—H20A	109.5
C5—C6—C1	121.8 (8)	O3—C20—H20B	109.5
N1—C7—C2	127.4 (9)	H20A—C20—H20B	109.5
N1—C7—H7	116.3	O3—C20—H20C	109.5
C2—C7—H7	116.3	H20A—C20—H20C	109.5
N1—C8—C9	108.8 (7)	H20B—C20—H20C	109.5
O7—U1—O1—C1	44.2 (8)	O1—C1—C2—C7	−0.1 (14)
O6—U1—O1—C1	−133.6 (8)	C6—C1—C2—C7	−177.6 (9)
O4—U1—O1—C1	129.9 (8)	C1—C2—C3—C4	0.3 (17)
O5—U1—O1—C1	140.4 (8)	C7—C2—C3—C4	178.0 (11)
N1—U1—O1—C1	−45.3 (8)	C2—C3—C4—C5	0.6 (18)
N2—U1—O1—C1	−49.3 (9)	C3—C4—C5—C6	−1.9 (17)
O7—U1—O4—C16	−140.9 (8)	C19—O2—C6—C5	−9.5 (15)
O6—U1—O4—C16	36.4 (8)	C19—O2—C6—C1	171.0 (10)
O1—U1—O4—C16	132.8 (8)	C4—C5—C6—O2	−177.1 (10)
O5—U1—O4—C16	122.5 (8)	C4—C5—C6—C1	2.3 (16)
N1—U1—O4—C16	−53.6 (9)	O1—C1—C6—O2	0.6 (13)
N2—U1—O4—C16	−47.7 (8)	C2—C1—C6—O2	178.1 (9)
O7—U1—O5—C17	−10.2 (12)	O1—C1—C6—C5	−178.8 (9)
O6—U1—O5—C17	168.7 (12)	C2—C1—C6—C5	−1.3 (14)
O4—U1—O5—C17	76.2 (12)	C8—N1—C7—C2	176.0 (9)
O1—U1—O5—C17	−99.1 (12)	U1—N1—C7—C2	−7.8 (14)
N1—U1—O5—C17	−108.8 (12)	C3—C2—C7—N1	168.4 (10)
N2—U1—O5—C17	93.2 (12)	C1—C2—C7—N1	−14.1 (15)
O7—U1—N1—C7	−64.3 (8)	C7—N1—C8—C9	127.7 (9)
O6—U1—N1—C7	118.0 (8)	U1—N1—C8—C9	−49.1 (8)
O4—U1—N1—C7	−150.8 (7)	C10—N2—C9—C8	128.6 (9)
O1—U1—N1—C7	26.2 (8)	U1—N2—C9—C8	−41.4 (9)
O5—U1—N1—C7	36.2 (10)	N1—C8—C9—N2	58.1 (10)
N2—U1—N1—C7	−156.8 (8)	C9—N2—C10—C11	−179.2 (10)
O7—U1—N1—C8	112.1 (6)	U1—N2—C10—C11	−10.2 (16)
O6—U1—N1—C8	−65.7 (6)	N2—C10—C11—C12	167.8 (11)
O4—U1—N1—C8	25.5 (7)	N2—C10—C11—C16	−12.8 (17)
O1—U1—N1—C8	−157.5 (6)	C10—C11—C12—C13	−179.6 (10)
O5—U1—N1—C8	−147.5 (6)	C16—C11—C12—C13	1.0 (16)
N2—U1—N1—C8	19.5 (6)	C11—C12—C13—C14	−1.1 (18)
O7—U1—N2—C10	114.9 (8)	C12—C13—C14—C15	−0.7 (18)
O6—U1—N2—C10	−65.6 (8)	C13—C14—C15—O3	−178.8 (11)
O4—U1—N2—C10	28.0 (8)	C13—C14—C15—C16	2.5 (18)
O1—U1—N2—C10	−152.3 (8)	C20—O3—C15—C14	1.3 (17)
O5—U1—N2—C10	10.4 (11)	C20—O3—C15—C16	−179.9 (10)
N1—U1—N2—C10	−156.4 (9)	U1—O4—C16—C15	−137.0 (8)
O7—U1—N2—C9	−76.1 (7)	U1—O4—C16—C11	44.3 (13)
O6—U1—N2—C9	103.4 (7)	C14—C15—C16—O4	178.7 (10)
O4—U1—N2—C9	−163.0 (7)	O3—C15—C16—O4	−0.1 (14)
O1—U1—N2—C9	16.7 (8)	C14—C15—C16—C11	−2.5 (16)
O5—U1—N2—C9	179.4 (6)	O3—C15—C16—C11	178.7 (8)
N1—U1—N2—C9	12.6 (6)	C12—C11—C16—O4	179.5 (9)
U1—O1—C1—C6	−139.4 (7)	C10—C11—C16—O4	0.2 (14)
U1—O1—C1—C2	43.2 (13)	C12—C11—C16—C15	0.7 (14)
O1—C1—C2—C3	177.4 (9)	C10—C11—C16—C15	−178.6 (9)
C6—C1—C2—C3	0.0 (14)	U1—O5—C17—C18	51.3 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1^i	0.83 (6)	2.53 (15)	3.059 (9)	124 (15)
O5—H5A···O2^i	0.83 (6)	2.19 (8)	2.952 (11)	154 (16)
C8—H8B···O7^ii	0.97	2.50	3.183 (11)	127
C17—H17B···O1^i	0.97	2.45	3.163 (19)	130
C18—H18C···O7	0.96	2.57	3.382 (19)	142
C19—H19A···O6^i	0.96	2.59	3.423 (13)	145

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1/2, y, −z+1/2.