Self-assembly of bis­(1,3-diphenyl­propane-1,3-dionato-κ²O,O′)bis­(thio­morpholine-κN)cobalt(II)

The mol­ecules of the title bis­(thio­morpholine) adduct of bis­(1,3-diphenyl­propane-1,3-dionato)cobalt(II), [Co(C₁₅H₁₂O₂)₂(C₄H₈NS)₂], in the crystal structure are positioned on an inversion center at the inter­section of a twofold rotation axis and a perpendicular mirror plane. The two thio­morpholine ligands bond to the octahedral cobalt(II) ion in the axial coordination sites (trans configuration).

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.109
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N21    -   H21    ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21A   ..  O11     ..       2.82 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; 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), Mercury (Bruno et al., 2002), RasTop (Valadon, 2004) and POVRay (Persistence of Vision Pty, 2004); software used to prepare material for publication: WinGX (Farrugia, 1999).

bis(1,3-diphenylpropane-1,3-dionato)bis(thiomorpholine)cobalt(II)

Crystal data

[Co(C15H12O2)2(C4H8NS)2]	F(000) = 1492
Mr = 711.79	Dx = 1.352 Mg m^−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 2147 reflections
a = 19.345 (2) Å	θ = 4–54°
b = 8.1767 (9) Å	µ = 0.65 mm^−1
c = 22.104 (2) Å	T = 295 K
V = 3496.4 (6) Å^3	Plate, orange
Z = 4	0.26 × 0.25 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur-3 CCD area-detector diffractometer	1597 independent reflections
Radiation source: fine-focus sealed tube	1493 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
ω scans	θmax = 25.1°, θmin = 4.1°
Absorption correction: analytical (Alcock, 1970)	h = −22→22
Tmin = 0.825, Tmax = 0.972	k = −9→9
23809 measured reflections	l = −26→26

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.33	w = 1/[σ^2(Fo^2) + (0.0351P)^2 + 3.3855P] where P = (Fo^2 + 2Fc^2)/3
1597 reflections	(Δ/σ)max = 0.001
113 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.2 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
Co	0.5	0	0.5	0.0375 (3)
S21	0.5	0.30100 (17)	0.71615 (6)	0.0668 (4)
O11	0.42603 (9)	0.1616 (2)	0.47184 (9)	0.0442 (5)
N21	0.5	0.0938 (4)	0.59383 (14)	0.0408 (8)
H21	0.5	0.0008	0.6165	0.049*
C11	0.43539 (14)	0.2643 (3)	0.42952 (12)	0.0375 (7)
C13	0.37154 (14)	0.3387 (3)	0.40346 (12)	0.0389 (7)
C18	0.31418 (16)	0.3614 (4)	0.43977 (14)	0.0509 (8)
H18	0.3155	0.3281	0.48	0.061*
C12	0.5	0.3134 (5)	0.40736 (18)	0.0426 (10)
H12	0.5	0.3854	0.3748	0.051*
C14	0.36748 (16)	0.3850 (4)	0.34340 (14)	0.0542 (9)
H14	0.4053	0.3694	0.3181	0.065*
C15	0.30783 (17)	0.4542 (5)	0.32074 (16)	0.0687 (11)
H15	0.3055	0.4838	0.2802	0.082*
C16	0.25201 (19)	0.4797 (4)	0.35778 (17)	0.0648 (10)
H16	0.2122	0.5286	0.3426	0.078*
C17	0.25493 (18)	0.4329 (5)	0.41721 (16)	0.0627 (9)
H17	0.217	0.4493	0.4424	0.075*
C21	0.43708 (15)	0.1776 (4)	0.61363 (14)	0.0527 (8)
H21A	0.3973	0.1196	0.5977	0.063*
H21B	0.4367	0.287	0.5967	0.063*
C22	0.43020 (17)	0.1897 (4)	0.68190 (15)	0.0594 (9)
H22A	0.4287	0.0803	0.6989	0.071*
H22B	0.3869	0.2434	0.6917	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co	0.0337 (4)	0.0459 (5)	0.0329 (4)	0	0	0.0078 (3)
S21	0.0814 (10)	0.0713 (9)	0.0477 (7)	0	0	−0.0127 (6)
O11	0.0377 (11)	0.0544 (12)	0.0406 (11)	0.0035 (10)	0.0051 (9)	0.0122 (10)
N21	0.0355 (19)	0.051 (2)	0.0358 (18)	0	0	0.0041 (16)
C11	0.0387 (17)	0.0408 (16)	0.0329 (15)	0.0022 (13)	0.0010 (13)	0.0019 (13)
C13	0.0351 (16)	0.0407 (16)	0.0410 (16)	−0.0013 (13)	−0.0013 (13)	0.0030 (13)
C18	0.0434 (19)	0.067 (2)	0.0428 (16)	0.0084 (16)	−0.0017 (14)	0.0035 (16)
C12	0.037 (2)	0.049 (2)	0.042 (2)	0	0	0.011 (2)
C14	0.0401 (18)	0.077 (2)	0.0451 (18)	−0.0002 (17)	−0.0026 (14)	0.0140 (17)
C15	0.048 (2)	0.105 (3)	0.053 (2)	−0.002 (2)	−0.0108 (17)	0.027 (2)
C16	0.0437 (19)	0.076 (2)	0.075 (2)	0.0079 (19)	−0.0171 (18)	0.013 (2)
C17	0.0439 (19)	0.086 (3)	0.059 (2)	0.0123 (19)	0.0015 (17)	−0.0032 (19)
C21	0.0416 (19)	0.068 (2)	0.0482 (18)	0.0052 (16)	0.0019 (15)	−0.0028 (16)
C22	0.054 (2)	0.073 (2)	0.0510 (19)	0.0087 (18)	0.0130 (16)	−0.0047 (17)

Geometric parameters (Å, º)

Co—O11^i	2.0447 (19)	C18—C17	1.380 (4)
Co—O11^ii	2.0447 (19)	C18—H18	0.93
Co—O11	2.0447 (19)	C12—C11^ii	1.401 (3)
Co—O11^iii	2.0447 (19)	C12—H12	0.93
Co—N21^iii	2.211 (3)	C14—C15	1.380 (4)
Co—N21	2.211 (3)	C14—H14	0.93
S21—C22	1.796 (4)	C15—C16	1.371 (5)
S21—C22^ii	1.796 (4)	C15—H15	0.93
S21—S21^iv	4.3536 (10)	C16—C17	1.369 (5)
O11—C11	1.270 (3)	C16—H16	0.93
N21—C21	1.464 (3)	C17—H17	0.93
N21—C21^ii	1.464 (3)	C21—C22	1.518 (4)
N21—H21	0.91	C21—H21A	0.97
C11—C12	1.401 (3)	C21—H21B	0.97
C11—C13	1.492 (4)	C22—H22A	0.97
C13—C18	1.382 (4)	C22—H22B	0.97
C13—C14	1.383 (4)
O11^i—Co—O11^ii	180.00 (13)	C17—C18—C13	120.9 (3)
O11^i—Co—O11	91.17 (11)	C17—C18—H18	119.5
O11^ii—Co—O11	88.83 (11)	C13—C18—H18	119.5
O11^i—Co—O11^iii	88.83 (11)	C11^ii—C12—C11	126.3 (4)
O11^ii—Co—O11^iii	91.17 (11)	C11^ii—C12—H12	116.9
O11—Co—O11^iii	180.00 (10)	C11—C12—H12	116.9
O11^i—Co—N21^iii	93.53 (8)	C15—C14—C13	120.6 (3)
O11^ii—Co—N21^iii	86.47 (8)	C15—C14—H14	119.7
O11—Co—N21^iii	86.47 (8)	C13—C14—H14	119.7
O11^iii—Co—N21^iii	93.53 (8)	C16—C15—C14	120.3 (3)
O11^i—Co—N21	86.47 (8)	C16—C15—H15	119.9
O11^ii—Co—N21	93.53 (8)	C14—C15—H15	119.9
O11—Co—N21	93.53 (8)	C17—C16—C15	119.9 (3)
O11^iii—Co—N21	86.47 (8)	C17—C16—H16	120.1
N21^iii—Co—N21	180	C15—C16—H16	120.1
C22—S21—C22^ii	97.5 (2)	C16—C17—C18	119.9 (3)
C22—S21—S21^iv	70.67 (12)	C16—C17—H17	120
C22^ii—S21—S21^iv	70.67 (12)	C18—C17—H17	120
C11—O11—Co	123.49 (17)	N21—C21—C22	113.6 (3)
C21—N21—C21^ii	112.5 (3)	N21—C21—H21A	108.8
C21—N21—Co	116.29 (17)	C22—C21—H21A	108.8
C21^ii—N21—Co	116.29 (17)	N21—C21—H21B	108.8
C21—N21—H21	103.1	C22—C21—H21B	108.8
C21^ii—N21—H21	103.1	H21A—C21—H21B	107.7
Co—N21—H21	103.1	C21—C22—S21	112.7 (2)
O11—C11—C12	125.0 (3)	C21—C22—H22A	109
O11—C11—C13	115.8 (2)	S21—C22—H22A	109
C12—C11—C13	119.1 (3)	C21—C22—H22B	109
C18—C13—C14	118.4 (3)	S21—C22—H22B	109
C18—C13—C11	119.7 (2)	H22A—C22—H22B	107.8
C14—C13—C11	121.9 (3)
O11^i—Co—O11—C11	−152.6 (3)	C12—C11—C13—C14	33.1 (4)
O11^ii—Co—O11—C11	27.4 (3)	C14—C13—C18—C17	−1.8 (5)
N21^iii—Co—O11—C11	−59.1 (2)	C11—C13—C18—C17	178.7 (3)
N21—Co—O11—C11	120.9 (2)	O11—C11—C12—C11^ii	−3.2 (7)
O11^i—Co—N21—C21	−67.4 (2)	C13—C11—C12—C11^ii	175.3 (3)
O11^ii—Co—N21—C21	112.6 (2)	C18—C13—C14—C15	0.9 (5)
O11—Co—N21—C21	23.5 (2)	C11—C13—C14—C15	−179.7 (3)
O11^iii—Co—N21—C21	−156.5 (2)	C13—C14—C15—C16	0.7 (6)
O11^i—Co—N21—C21^ii	156.5 (2)	C14—C15—C16—C17	−1.4 (6)
O11^ii—Co—N21—C21^ii	−23.5 (2)	C15—C16—C17—C18	0.5 (6)
O11—Co—N21—C21^ii	−112.6 (2)	C13—C18—C17—C16	1.2 (5)
O11^iii—Co—N21—C21^ii	67.4 (2)	C21^ii—N21—C21—C22	−61.2 (4)
Co—O11—C11—C12	−18.0 (4)	Co—N21—C21—C22	161.2 (2)
Co—O11—C11—C13	163.46 (18)	N21—C21—C22—S21	60.5 (4)
O11—C11—C13—C18	31.2 (4)	C22^ii—S21—C22—C21	−51.6 (3)
C12—C11—C13—C18	−147.5 (3)	S21^iv—S21—C22—C21	−118.0 (3)
O11—C11—C13—C14	−148.3 (3)

Symmetry codes: (i) x, −y, −z+1; (ii) −x+1, y, z; (iii) −x+1, −y, −z+1; (iv) −x+1, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···O11^i	0.97	2.82	3.362 (4)	116
N21—H21···C12^i	0.91	2.62	3.329 (5)	135

Symmetry code: (i) x, −y, −z+1.