Bis[2-(dimethyl­amino)ethanol-κ²N,O](2,4-penta­nedionato-κ²O,O′)nickel(II) acetate

The Ni atom in the title complex, [Ni(C₅H₇O₂)(C₄H₁₁NO)₂](C₂H₃O₂), has distorted octa­hedral coordination. The O atoms of the acetate ion are hydrogen bonded to the OH groups of the 2-(dimethyl­amino)ethanol ligands.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.024
• wR factor = 0.063
• Data-to-parameter ratio = 20.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.57
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O1      ..       7.42 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O2      ..       7.14 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O3      ..       5.41 su

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           28.28
           From the CIF: _reflns_number_total               4812
           Count of symmetry unique reflns         2735
           Completeness (_total/calc)            175.94%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2077
           Fraction of Friedel pairs measured     0.759
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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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.

Bis[2-(dimethylamino)ethanol-κ²N,O](2,4-pentanedionate-κ²O,O')nickel(II) acetate

Crystal data

[Ni(C5H7O2)(C4H11NO)2](C2H3O2)	Dx = 1.355 Mg m^−3
Mr = 395.14	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 8795 reflections
a = 8.5456 (10) Å	θ = 2.6–30.6°
b = 12.5165 (15) Å	µ = 1.03 mm^−1
c = 18.109 (2) Å	T = 100 K
V = 1937.0 (4) Å^3	Block, blue
Z = 4	0.52 × 0.52 × 0.34 mm
F(000) = 848

Data collection

Bruker SMART APEX CCD diffractometer	4812 independent reflections
Radiation source: fine-focus sealed tube	4717 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003)	h = −11→11
Tmin = 0.571, Tmax = 0.704	k = −16→16
19915 measured reflections	l = −23→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.063	w = 1/[σ^2(Fo^2) + (0.0383P)^2 + 0.3423P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.002
4812 reflections	Δρmax = 0.66 e Å^−3
230 parameters	Δρmin = −0.26 e Å^−3
1 restraint	Absolute structure: (Flack, 1983), 2077 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.008 (8)

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
C1	0.60500 (18)	0.66196 (13)	0.60074 (9)	0.0249 (3)
H1A	0.5478	0.6815	0.6463	0.030*
H1B	0.6341	0.7286	0.5747	0.030*
C2	0.7508 (2)	0.59964 (14)	0.62032 (9)	0.0276 (3)
H2A	0.8237	0.6459	0.6483	0.033*
H2B	0.7226	0.5380	0.6519	0.033*
C3	0.9219 (2)	0.64728 (14)	0.51841 (10)	0.0312 (3)
H3A	0.8543	0.7085	0.5074	0.047*
H3B	0.9694	0.6211	0.4726	0.047*
H3C	1.0045	0.6693	0.5528	0.047*
C4	0.9352 (2)	0.47273 (15)	0.57179 (11)	0.0343 (4)
H4A	1.0156	0.4990	0.6058	0.051*
H4B	0.9851	0.4453	0.5269	0.051*
H4C	0.8757	0.4153	0.5956	0.051*
C5	0.51096 (19)	0.29876 (12)	0.49791 (8)	0.0236 (3)
H5A	0.4713	0.2410	0.5303	0.028*
H5B	0.5697	0.2656	0.4567	0.028*
C6	0.37488 (18)	0.36292 (12)	0.46764 (8)	0.0242 (3)
H6A	0.3088	0.3167	0.4361	0.029*
H6B	0.3098	0.3896	0.5089	0.029*
C7	0.31447 (19)	0.53981 (14)	0.42011 (10)	0.0280 (3)
H7A	0.2226	0.5138	0.3932	0.042*
H7B	0.3583	0.6019	0.3944	0.042*
H7C	0.2836	0.5604	0.4702	0.042*
C8	0.46915 (19)	0.41886 (14)	0.34786 (8)	0.0250 (3)
H8A	0.5406	0.3577	0.3494	0.038*
H8B	0.5184	0.4776	0.3206	0.038*
H8C	0.3719	0.3980	0.3231	0.038*
C9	0.96996 (19)	0.39287 (13)	0.31741 (9)	0.0252 (3)
H9A	1.0472	0.3658	0.3528	0.038*
H9B	1.0237	0.4318	0.2779	0.038*
H9C	0.9118	0.3328	0.2962	0.038*
C10	0.85782 (18)	0.46704 (11)	0.35649 (7)	0.0197 (3)
C11	0.83125 (18)	0.56826 (12)	0.32549 (8)	0.0221 (3)
H11	0.8880	0.5861	0.2821	0.027*
C12	0.72739 (18)	0.64519 (12)	0.35360 (8)	0.0206 (3)
C13	0.7027 (2)	0.74607 (12)	0.30883 (9)	0.0269 (3)
H13A	0.5933	0.7500	0.2928	0.040*
H13B	0.7712	0.7449	0.2654	0.040*
H13C	0.7275	0.8085	0.3393	0.040*
N1	0.82795 (14)	0.56124 (10)	0.55227 (7)	0.0204 (2)
N2	0.43389 (16)	0.45400 (11)	0.42390 (7)	0.0210 (3)
Ni1	0.64358 (2)	0.509957 (13)	0.479776 (9)	0.01552 (5)
O1	0.50721 (13)	0.59785 (9)	0.55439 (6)	0.0199 (2)
H1	0.437 (2)	0.5628 (17)	0.5761 (11)	0.030*
O2	0.61238 (12)	0.36779 (8)	0.53916 (6)	0.0199 (2)
H2	0.570 (2)	0.3759 (17)	0.5822 (10)	0.030*
O3	0.79365 (13)	0.42992 (8)	0.41460 (6)	0.0203 (2)
O4	0.65014 (14)	0.63834 (8)	0.41335 (6)	0.0210 (2)
C14	0.34835 (19)	0.41806 (11)	0.67055 (7)	0.0211 (3)
C15	0.2287 (2)	0.36800 (16)	0.72201 (10)	0.0346 (4)
H15A	0.1448	0.4194	0.7318	0.052*
H15B	0.2796	0.3483	0.7686	0.052*
H15C	0.1846	0.3040	0.6988	0.052*
O5	0.47920 (13)	0.37265 (9)	0.66591 (6)	0.0242 (2)
O6	0.30770 (13)	0.50020 (10)	0.63573 (6)	0.0268 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0249 (8)	0.0223 (7)	0.0274 (7)	0.0002 (6)	0.0004 (6)	−0.0087 (6)
C2	0.0276 (8)	0.0310 (8)	0.0242 (7)	−0.0027 (7)	−0.0026 (6)	−0.0019 (6)
C3	0.0277 (8)	0.0347 (8)	0.0313 (8)	−0.0114 (7)	0.0005 (7)	−0.0001 (8)
C4	0.0261 (8)	0.0322 (9)	0.0447 (10)	0.0049 (7)	−0.0091 (7)	−0.0028 (8)
C5	0.0277 (7)	0.0176 (6)	0.0255 (7)	−0.0038 (6)	0.0004 (6)	−0.0010 (5)
C6	0.0213 (7)	0.0252 (7)	0.0262 (7)	−0.0066 (6)	0.0003 (6)	−0.0017 (5)
C7	0.0220 (7)	0.0299 (8)	0.0320 (8)	0.0042 (6)	−0.0078 (6)	−0.0044 (6)
C8	0.0267 (8)	0.0274 (8)	0.0210 (7)	−0.0019 (6)	−0.0034 (6)	−0.0029 (6)
C9	0.0272 (8)	0.0224 (8)	0.0260 (8)	0.0001 (6)	0.0077 (6)	−0.0026 (6)
C10	0.0184 (6)	0.0214 (6)	0.0191 (6)	−0.0025 (6)	0.0015 (5)	−0.0022 (5)
C11	0.0245 (7)	0.0217 (7)	0.0201 (6)	−0.0012 (6)	0.0044 (6)	0.0016 (5)
C12	0.0207 (7)	0.0196 (7)	0.0214 (7)	−0.0021 (5)	−0.0007 (5)	0.0028 (5)
C13	0.0319 (8)	0.0220 (7)	0.0269 (7)	0.0004 (6)	0.0032 (7)	0.0076 (6)
N1	0.0167 (6)	0.0213 (6)	0.0231 (6)	−0.0013 (5)	−0.0012 (5)	−0.0007 (5)
N2	0.0209 (6)	0.0215 (6)	0.0205 (6)	−0.0008 (5)	−0.0012 (5)	−0.0018 (5)
Ni1	0.01556 (8)	0.01454 (8)	0.01646 (8)	−0.00044 (6)	0.00090 (6)	−0.00003 (6)
O1	0.0183 (5)	0.0203 (5)	0.0210 (5)	−0.0010 (4)	0.0011 (4)	−0.0012 (4)
O2	0.0216 (5)	0.0188 (5)	0.0194 (5)	−0.0012 (4)	0.0016 (4)	0.0001 (4)
O3	0.0222 (5)	0.0189 (5)	0.0200 (5)	0.0010 (4)	0.0034 (4)	0.0008 (4)
O4	0.0229 (5)	0.0181 (5)	0.0218 (4)	0.0013 (4)	0.0033 (4)	0.0020 (4)
C14	0.0235 (6)	0.0221 (6)	0.0176 (6)	−0.0032 (6)	0.0005 (6)	−0.0041 (5)
C15	0.0376 (10)	0.0331 (9)	0.0330 (9)	0.0019 (8)	0.0160 (8)	0.0036 (7)
O5	0.0244 (5)	0.0285 (6)	0.0197 (5)	0.0016 (4)	0.0004 (4)	0.0014 (4)
O6	0.0234 (5)	0.0239 (5)	0.0330 (5)	0.0010 (4)	0.0047 (4)	0.0041 (5)

Geometric parameters (Å, º)

C1—O1	1.4306 (18)	C8—H8C	0.9800
C1—C2	1.512 (2)	C9—C10	1.510 (2)
C1—H1A	0.9900	C9—H9A	0.9800
C1—H1B	0.9900	C9—H9B	0.9800
C2—N1	1.478 (2)	C9—H9C	0.9800
C2—H2A	0.9900	C10—O3	1.2744 (18)
C2—H2B	0.9900	C10—C11	1.404 (2)
C3—N1	1.477 (2)	C11—C12	1.405 (2)
C3—H3A	0.9800	C11—H11	0.9500
C3—H3B	0.9800	C12—O4	1.2704 (18)
C3—H3C	0.9800	C12—C13	1.515 (2)
C4—N1	1.480 (2)	C13—H13A	0.9800
C4—H4A	0.9800	C13—H13B	0.9800
C4—H4B	0.9800	C13—H13C	0.9800
C4—H4C	0.9800	N1—Ni1	2.1489 (13)
C5—O2	1.4337 (18)	N2—Ni1	2.1738 (13)
C5—C6	1.516 (2)	Ni1—O4	2.0080 (10)
C5—H5A	0.9900	Ni1—O3	2.0102 (11)
C5—H5B	0.9900	Ni1—O1	2.0962 (11)
C6—N2	1.477 (2)	Ni1—O2	2.0961 (11)
C6—H6A	0.9900	O1—H1	0.839 (18)
C6—H6B	0.9900	O2—H2	0.867 (18)
C7—N2	1.483 (2)	C14—O6	1.2550 (19)
C7—H7A	0.9800	C14—O5	1.257 (2)
C7—H7B	0.9800	C14—C15	1.519 (2)
C7—H7C	0.9800	C15—H15A	0.9800
C8—N2	1.4765 (19)	C15—H15B	0.9800
C8—H8A	0.9800	C15—H15C	0.9800
C8—H8B	0.9800
O1—C1—C2	109.25 (12)	C10—C11—C12	125.15 (14)
O1—C1—H1A	109.8	C10—C11—H11	117.4
C2—C1—H1A	109.8	C12—C11—H11	117.4
O1—C1—H1B	109.8	O4—C12—C11	126.19 (14)
C2—C1—H1B	109.8	O4—C12—C13	116.07 (14)
H1A—C1—H1B	108.3	C11—C12—C13	117.73 (13)
N1—C2—C1	109.86 (13)	C12—C13—H13A	109.5
N1—C2—H2A	109.7	C12—C13—H13B	109.5
C1—C2—H2A	109.7	H13A—C13—H13B	109.5
N1—C2—H2B	109.7	C12—C13—H13C	109.5
C1—C2—H2B	109.7	H13A—C13—H13C	109.5
H2A—C2—H2B	108.2	H13B—C13—H13C	109.5
N1—C3—H3A	109.5	C3—N1—C2	110.58 (13)
N1—C3—H3B	109.5	C3—N1—C4	107.96 (13)
H3A—C3—H3B	109.5	C2—N1—C4	108.68 (13)
N1—C3—H3C	109.5	C3—N1—Ni1	111.29 (10)
H3A—C3—H3C	109.5	C2—N1—Ni1	106.23 (9)
H3B—C3—H3C	109.5	C4—N1—Ni1	112.09 (10)
N1—C4—H4A	109.5	C8—N2—C6	109.87 (12)
N1—C4—H4B	109.5	C8—N2—C7	108.25 (12)
H4A—C4—H4B	109.5	C6—N2—C7	110.41 (13)
N1—C4—H4C	109.5	C8—N2—Ni1	111.21 (10)
H4A—C4—H4C	109.5	C6—N2—Ni1	106.29 (9)
H4B—C4—H4C	109.5	C7—N2—Ni1	110.82 (10)
O2—C5—C6	109.45 (12)	O4—Ni1—O3	91.68 (4)
O2—C5—H5A	109.8	O4—Ni1—O1	88.95 (4)
C6—C5—H5A	109.8	O3—Ni1—O1	174.06 (5)
O2—C5—H5B	109.8	O4—Ni1—O2	171.97 (4)
C6—C5—H5B	109.8	O3—Ni1—O2	87.67 (4)
H5A—C5—H5B	108.2	O1—Ni1—O2	92.53 (4)
N2—C6—C5	109.94 (12)	O4—Ni1—N1	96.11 (5)
N2—C6—H6A	109.7	O3—Ni1—N1	92.28 (5)
C5—C6—H6A	109.7	O1—Ni1—N1	81.78 (5)
N2—C6—H6B	109.7	O2—Ni1—N1	91.92 (5)
C5—C6—H6B	109.7	O4—Ni1—N2	90.11 (5)
H6A—C6—H6B	108.2	O3—Ni1—N2	95.28 (5)
N2—C7—H7A	109.5	O1—Ni1—N2	90.63 (5)
N2—C7—H7B	109.5	O2—Ni1—N2	81.98 (5)
H7A—C7—H7B	109.5	N1—Ni1—N2	170.07 (5)
N2—C7—H7C	109.5	C1—O1—Ni1	110.35 (9)
H7A—C7—H7C	109.5	C1—O1—H1	115.7 (14)
H7B—C7—H7C	109.5	Ni1—O1—H1	115.1 (15)
N2—C8—H8A	109.5	C5—O2—Ni1	108.73 (8)
N2—C8—H8B	109.5	C5—O2—H2	106.5 (14)
H8A—C8—H8B	109.5	Ni1—O2—H2	114.6 (14)
N2—C8—H8C	109.5	C10—O3—Ni1	125.29 (9)
H8A—C8—H8C	109.5	C12—O4—Ni1	125.36 (10)
H8B—C8—H8C	109.5	O6—C14—O5	125.65 (14)
C10—C9—H9A	109.5	O6—C14—C15	117.39 (15)
C10—C9—H9B	109.5	O5—C14—C15	116.95 (14)
H9A—C9—H9B	109.5	C14—C15—H15A	109.5
C10—C9—H9C	109.5	C14—C15—H15B	109.5
H9A—C9—H9C	109.5	H15A—C15—H15B	109.5
H9B—C9—H9C	109.5	C14—C15—H15C	109.5
O3—C10—C11	126.12 (14)	H15A—C15—H15C	109.5
O3—C10—C9	115.84 (13)	H15B—C15—H15C	109.5
C11—C10—C9	118.03 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6	0.84 (2)	1.73 (2)	2.5634 (16)	169 (2)
O2—H2···O5	0.87 (2)	1.70 (2)	2.5627 (15)	172 (2)