[2-(N,N-Dimethyl­amino)ethanol-κ²N,O]bis­(2,4-penta­nedionato-κ²O,O′)manganese(II)

The crystalline title complex, [Mn(C₅H₇O₂)₂(C₄H₁₁N)], was prepared as a possible precursor for chemical vapour deposition of manganese(II) oxide, MnO. Two 2,4-penta­ne­dionate and one N,N-dimethyl­amino­ethanol ligand are coordinated to the Mn^II atom in a slightly distorted octa­hedral geometry. The Mn complex is isostructural with the analogous Ni, Co and Zn complexes.

Key indicators

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.096
• Data-to-parameter ratio = 21.5

checkCIF/PLATON results

No syntax errors found



Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            yellowish
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.62
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mn1    -   O4      ..       5.87 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

[2-(N,N-Dimethylamino)ethanolato-κ²N,O]bis(2,4-pentanedionate- κ²O,O')manganese(II)

Crystal data

[Mn(C5H7O2)2(C4H11N)]	F(000) = 362
Mr = 342.29	Dx = 1.306 Mg m^−3
Triclinic, P1	Melting point: 125 K
a = 7.6392 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5533 (19) Å	Cell parameters from 5563 reflections
c = 11.766 (2) Å	θ = 2.3–30.5°
α = 105.235 (3)°	µ = 0.78 mm^−1
β = 103.187 (3)°	T = 110 K
γ = 98.154 (3)°	Plate, yellowish
V = 870.3 (3) Å^3	0.37 × 0.27 × 0.02 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4296 independent reflections
Radiation source: fine-focus sealed tube	3711 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003)	h = −10→10
Tmin = 0.772, Tmax = 0.99	k = −14→14
8862 measured reflections	l = −15→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.054P)^2 + 0.2295P] where P = (Fo^2 + 2Fc^2)/3
4296 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.63 e Å^−3
1 restraint	Δρmin = −0.24 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
Mn1	0.41002 (3)	0.52507 (2)	0.26919 (2)	0.01523 (9)
O1	0.64115 (16)	0.58537 (13)	0.44133 (11)	0.0222 (3)
H1	0.647 (4)	0.616 (2)	0.5166 (16)	0.046 (7)*
C1	0.8027 (2)	0.53354 (19)	0.43383 (16)	0.0235 (3)
H1A	0.7965	0.4503	0.4580	0.028*
H1B	0.9135	0.6003	0.4898	0.028*
C2	0.8128 (2)	0.50392 (18)	0.30232 (16)	0.0234 (3)
H2A	0.8365	0.5894	0.2829	0.028*
H2B	0.9164	0.4592	0.2930	0.028*
N2	0.64001 (19)	0.41662 (14)	0.21577 (12)	0.0187 (3)
C3	0.6198 (3)	0.27949 (18)	0.22543 (19)	0.0279 (4)
H3A	0.5084	0.2218	0.1638	0.042*
H3B	0.6103	0.2814	0.3075	0.042*
H3C	0.7274	0.2439	0.2115	0.042*
C4	0.6427 (3)	0.4107 (2)	0.08974 (16)	0.0290 (4)
H4A	0.6591	0.5018	0.0826	0.044*
H4B	0.5262	0.3557	0.0321	0.044*
H4C	0.7448	0.3707	0.0706	0.044*
C5	0.1300 (3)	0.13877 (18)	0.30038 (18)	0.0290 (4)
H5A	0.2454	0.1235	0.3460	0.044*
H5B	0.0613	0.0554	0.2360	0.044*
H5C	0.0558	0.1669	0.3565	0.044*
C6	0.1721 (2)	0.24728 (16)	0.24285 (15)	0.0193 (3)
C7	0.0875 (2)	0.22396 (17)	0.11908 (16)	0.0228 (3)
H7	0.0088	0.1384	0.0752	0.027*
C8	0.1086 (2)	0.31680 (17)	0.05302 (15)	0.0208 (3)
C9	−0.0018 (3)	0.2782 (2)	−0.07946 (16)	0.0284 (4)
H9A	−0.0697	0.3479	−0.0916	0.043*
H9B	−0.0889	0.1923	−0.1009	0.043*
H9C	0.0814	0.2693	−0.1319	0.043*
O2	0.28447 (16)	0.35572 (11)	0.31465 (10)	0.0193 (2)
O3	0.21268 (16)	0.43198 (12)	0.09686 (11)	0.0220 (2)
C10	0.1792 (3)	0.85390 (18)	0.45908 (18)	0.0276 (4)
H10A	0.0508	0.8315	0.4093	0.041*
H10B	0.2257	0.9514	0.4844	0.041*
H10C	0.1865	0.8241	0.5319	0.041*
C11	0.2941 (2)	0.78407 (17)	0.38454 (15)	0.0195 (3)
C12	0.4110 (2)	0.86151 (17)	0.34015 (16)	0.0220 (3)
H12	0.4233	0.9562	0.3679	0.026*
C13	0.5117 (2)	0.81212 (16)	0.25853 (15)	0.0204 (3)
C14	0.6188 (3)	0.91068 (19)	0.2129 (2)	0.0369 (5)
H14A	0.7503	0.9115	0.2395	0.055*
H14B	0.5983	1.0009	0.2467	0.055*
H14C	0.5771	0.8835	0.1232	0.055*
O4	0.27152 (16)	0.65827 (12)	0.36526 (11)	0.0214 (2)
O5	0.52144 (17)	0.69063 (11)	0.21747 (11)	0.0212 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.01576 (13)	0.01687 (14)	0.01353 (13)	0.00392 (9)	0.00379 (9)	0.00547 (9)
O1	0.0182 (6)	0.0338 (7)	0.0145 (6)	0.0078 (5)	0.0040 (5)	0.0066 (5)
C1	0.0177 (8)	0.0343 (9)	0.0187 (8)	0.0074 (7)	0.0030 (6)	0.0090 (7)
C2	0.0181 (8)	0.0305 (9)	0.0221 (8)	0.0041 (7)	0.0060 (6)	0.0090 (7)
N2	0.0189 (7)	0.0224 (7)	0.0164 (6)	0.0056 (5)	0.0054 (5)	0.0073 (5)
C3	0.0249 (9)	0.0260 (9)	0.0368 (10)	0.0098 (7)	0.0114 (8)	0.0116 (8)
C4	0.0323 (10)	0.0410 (11)	0.0190 (9)	0.0155 (8)	0.0114 (7)	0.0102 (8)
C5	0.0324 (10)	0.0231 (9)	0.0347 (10)	0.0036 (7)	0.0121 (8)	0.0129 (8)
C6	0.0171 (7)	0.0189 (8)	0.0239 (8)	0.0052 (6)	0.0093 (6)	0.0060 (6)
C7	0.0211 (8)	0.0203 (8)	0.0224 (8)	0.0018 (6)	0.0046 (7)	0.0017 (6)
C8	0.0173 (8)	0.0260 (9)	0.0164 (8)	0.0070 (6)	0.0040 (6)	0.0017 (6)
C9	0.0264 (9)	0.0345 (10)	0.0172 (8)	0.0047 (7)	0.0003 (7)	0.0021 (7)
O2	0.0205 (6)	0.0214 (6)	0.0162 (5)	0.0032 (4)	0.0050 (4)	0.0068 (5)
O3	0.0212 (6)	0.0241 (6)	0.0179 (6)	0.0018 (5)	0.0019 (5)	0.0067 (5)
C10	0.0284 (9)	0.0263 (9)	0.0287 (9)	0.0081 (7)	0.0125 (8)	0.0044 (7)
C11	0.0185 (8)	0.0232 (8)	0.0145 (7)	0.0055 (6)	0.0022 (6)	0.0036 (6)
C12	0.0256 (8)	0.0156 (8)	0.0231 (8)	0.0036 (6)	0.0069 (7)	0.0038 (6)
C13	0.0219 (8)	0.0202 (8)	0.0171 (8)	0.0007 (6)	0.0028 (6)	0.0065 (6)
C14	0.0553 (13)	0.0225 (10)	0.0374 (11)	0.0016 (9)	0.0270 (10)	0.0082 (8)
O4	0.0217 (6)	0.0202 (6)	0.0231 (6)	0.0047 (5)	0.0081 (5)	0.0061 (5)
O5	0.0266 (6)	0.0188 (6)	0.0194 (6)	0.0043 (5)	0.0086 (5)	0.0063 (5)

Geometric parameters (Å, º)

Mn1—O3	2.1183 (12)	C5—H5B	0.9800
Mn1—O4	2.1226 (12)	C5—H5C	0.9800
Mn1—O5	2.1262 (12)	C6—O2	1.282 (2)
Mn1—O2	2.1565 (11)	C6—C7	1.392 (2)
Mn1—O1	2.2354 (12)	C7—C8	1.415 (2)
Mn1—N2	2.3427 (14)	C7—H7	0.9500
O1—C1	1.430 (2)	C8—O3	1.259 (2)
O1—H1	0.847 (16)	C8—C9	1.509 (2)
C1—C2	1.518 (2)	C9—H9A	0.9800
C1—H1A	0.9900	C9—H9B	0.9800
C1—H1B	0.9900	C9—H9C	0.9800
C2—N2	1.475 (2)	C10—C11	1.509 (2)
C2—H2A	0.9900	C10—H10A	0.9800
C2—H2B	0.9900	C10—H10B	0.9800
N2—C3	1.470 (2)	C10—H10C	0.9800
N2—C4	1.473 (2)	C11—O4	1.266 (2)
C3—H3A	0.9800	C11—C12	1.403 (2)
C3—H3B	0.9800	C12—C13	1.404 (2)
C3—H3C	0.9800	C12—H12	0.9500
C4—H4A	0.9800	C13—O5	1.265 (2)
C4—H4B	0.9800	C13—C14	1.514 (2)
C4—H4C	0.9800	C14—H14A	0.9800
C5—C6	1.508 (2)	C14—H14B	0.9800
C5—H5A	0.9800	C14—H14C	0.9800
O3—Mn1—O4	102.65 (5)	H4B—C4—H4C	109.5
O3—Mn1—O5	94.01 (5)	C6—C5—H5A	109.5
O4—Mn1—O5	86.19 (5)	C6—C5—H5B	109.5
O3—Mn1—O2	83.37 (5)	H5A—C5—H5B	109.5
O4—Mn1—O2	93.26 (5)	C6—C5—H5C	109.5
O5—Mn1—O2	177.15 (4)	H5A—C5—H5C	109.5
O3—Mn1—O1	168.27 (5)	H5B—C5—H5C	109.5
O4—Mn1—O1	88.12 (5)	O2—C6—C7	125.26 (15)
O5—Mn1—O1	91.31 (5)	O2—C6—C5	115.86 (15)
O2—Mn1—O1	91.47 (5)	C7—C6—C5	118.88 (16)
O3—Mn1—N2	94.92 (5)	C6—C7—C8	125.58 (16)
O4—Mn1—N2	162.14 (5)	C6—C7—H7	117.2
O5—Mn1—N2	89.40 (5)	C8—C7—H7	117.2
O2—Mn1—N2	91.96 (5)	O3—C8—C7	124.82 (15)
O1—Mn1—N2	74.67 (5)	O3—C8—C9	116.37 (16)
C1—O1—Mn1	116.95 (10)	C7—C8—C9	118.81 (16)
C1—O1—H1	107.6 (18)	C8—C9—H9A	109.5
Mn1—O1—H1	133.1 (18)	C8—C9—H9B	109.5
O1—C1—C2	108.00 (13)	H9A—C9—H9B	109.5
O1—C1—H1A	110.1	C8—C9—H9C	109.5
C2—C1—H1A	110.1	H9A—C9—H9C	109.5
O1—C1—H1B	110.1	H9B—C9—H9C	109.5
C2—C1—H1B	110.1	C6—O2—Mn1	128.69 (10)
H1A—C1—H1B	108.4	C8—O3—Mn1	130.79 (11)
N2—C2—C1	111.12 (14)	C11—C10—H10A	109.5
N2—C2—H2A	109.4	C11—C10—H10B	109.5
C1—C2—H2A	109.4	H10A—C10—H10B	109.5
N2—C2—H2B	109.4	C11—C10—H10C	109.5
C1—C2—H2B	109.4	H10A—C10—H10C	109.5
H2A—C2—H2B	108.0	H10B—C10—H10C	109.5
C3—N2—C4	108.67 (14)	O4—C11—C12	125.85 (15)
C3—N2—C2	110.75 (14)	O4—C11—C10	115.88 (15)
C4—N2—C2	109.18 (14)	C12—C11—C10	118.24 (15)
C3—N2—Mn1	113.57 (10)	C11—C12—C13	126.11 (15)
C4—N2—Mn1	110.35 (10)	C11—C12—H12	116.9
C2—N2—Mn1	104.21 (10)	C13—C12—H12	116.9
N2—C3—H3A	109.5	O5—C13—C12	126.07 (15)
N2—C3—H3B	109.5	O5—C13—C14	115.52 (15)
H3A—C3—H3B	109.5	C12—C13—C14	118.40 (15)
N2—C3—H3C	109.5	C13—C14—H14A	109.5
H3A—C3—H3C	109.5	C13—C14—H14B	109.5
H3B—C3—H3C	109.5	H14A—C14—H14B	109.5
N2—C4—H4A	109.5	C13—C14—H14C	109.5
N2—C4—H4B	109.5	H14A—C14—H14C	109.5
H4A—C4—H4B	109.5	H14B—C14—H14C	109.5
N2—C4—H4C	109.5	C11—O4—Mn1	127.53 (11)
H4A—C4—H4C	109.5	C13—O5—Mn1	127.17 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.85 (2)	1.87 (2)	2.6777 (17)	160 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.