trans-Diaqua­bis(quinoline-2-carboxyl­ato)nickel(II) dimethyl­formamide disolvate

In the title monomeric complex, [Ni(C₂₀H₁₂N₂O₄)₂(H₂O)₂]·2C₃H₇NO, the cation lies on a centre of symmetry in a distorted octa­hedral environment. The organic ligand acts in an O,N-chelating mode, defining the equatorial plane, while two aqua mol­ecules occupy the axial sites. The mol­ecules bind to each other and to the uncoordinated solvent molecules in layers parallel to (100) through a complex hydrogen-bonding scheme.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.114
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97.

trans-Diaquabis(quinoline-2-carboxylato)nickel(II) dimethylformamide disolvate

Crystal data

[Ni(C20H12N2O4)(H2O)2]·2(C3H7NO)	F(000) = 612
Mr = 585.25	Dx = 1.438 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9931 reflections
a = 11.447 (2) Å	θ = 3.1–27.5°
b = 9.3143 (19) Å	µ = 0.77 mm^−1
c = 12.780 (3) Å	T = 294 K
β = 97.38 (3)°	Block, green
V = 1351.4 (5) Å^3	0.50 × 0.46 × 0.13 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID diffractometer	3082 independent reflections
Radiation source: fine-focus sealed tube	2352 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −14→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
Tmin = 0.698, Tmax = 0.906	l = −14→16
12666 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.064P)^2] where P = (Fo^2 + 2Fc^2)/3
3082 reflections	(Δ/σ)max < 0.001
188 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3
0 constraints

Special details

Experimental. IR (KBr disk; ν/cm^-1): 3369 (s), 3104 (w), 2927 (w), 1655 (versus), 1633 (versus), 1569 (m), 1510 (w),1463 (s), 1433 (w), 1387 (versus), 1295 (w), 1257 (w), 1208 (w), 1181 (m), 1153 (m), 1100 (m), 1059 (w), 1026 (w), 987 (w), 964 (w), 900 (m), 862 (m), 807 (s), 776 (s), 749 (w), 663 (s), 639 (m), 606 (m), 523 (w), 501 (w), 407 (w).

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
Ni1	1.0000	0.0000	0.0000	0.03061 (14)
N1	0.93622 (14)	0.21791 (18)	−0.02139 (12)	0.0322 (4)
N2	0.5631 (2)	0.8475 (3)	0.1016 (2)	0.0747 (7)
O1	1.10796 (16)	0.24073 (18)	−0.23033 (12)	0.0523 (4)
O2	1.08621 (13)	0.06491 (17)	−0.11794 (10)	0.0382 (3)
O3	1.13940 (17)	0.0653 (2)	0.11239 (13)	0.0444 (4)
O4	0.64215 (19)	0.8617 (3)	−0.0519 (2)	0.0875 (7)
C1	0.97637 (18)	0.2770 (2)	−0.10357 (14)	0.0340 (4)
C2	0.9446 (2)	0.4146 (2)	−0.14198 (16)	0.0427 (5)
H2	0.9770	0.4522	−0.1992	0.051*
C3	0.8657 (2)	0.4922 (2)	−0.0943 (2)	0.0444 (6)
H3	0.8410	0.5819	−0.1204	0.053*
C4	0.82208 (18)	0.4353 (2)	−0.00526 (17)	0.0400 (5)
C5	0.7463 (2)	0.5134 (3)	0.0533 (2)	0.0518 (6)
H5	0.7184	0.6027	0.0291	0.062*
C6	0.7143 (2)	0.4608 (3)	0.1431 (2)	0.0574 (7)
H6	0.6665	0.5152	0.1814	0.069*
C7	0.7522 (2)	0.3243 (3)	0.1796 (2)	0.0553 (6)
H7	0.7296	0.2888	0.2419	0.066*
C8	0.82284 (19)	0.2429 (3)	0.12353 (16)	0.0425 (5)
H8	0.8458	0.1514	0.1469	0.051*
C9	1.06400 (19)	0.1885 (2)	−0.15609 (15)	0.0368 (5)
C10	0.86042 (17)	0.2974 (2)	0.03121 (15)	0.0349 (4)
C11	0.5739 (4)	0.8862 (7)	0.2121 (4)	0.138 (2)
H11A	0.5622	0.8026	0.2533	0.207*
H11B	0.5157	0.9571	0.2225	0.207*
H11C	0.6511	0.9246	0.2336	0.207*
C12	0.4657 (3)	0.7588 (5)	0.0623 (4)	0.1122 (15)
H12A	0.4661	0.7431	−0.0118	0.168*
H12B	0.3936	0.8053	0.0738	0.168*
H12C	0.4718	0.6683	0.0986	0.168*
C13	0.6422 (2)	0.8915 (3)	0.0427 (3)	0.0775 (9)
H13	0.7029	0.9494	0.0745	0.093*
H10	1.127 (2)	0.119 (3)	0.159 (2)	0.054 (8)*
H9	1.199 (2)	0.090 (3)	0.095 (2)	0.059 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0425 (2)	0.0257 (2)	0.0247 (2)	0.00216 (14)	0.00815 (16)	0.00158 (13)
N1	0.0406 (9)	0.0278 (9)	0.0279 (7)	0.0022 (7)	0.0037 (7)	0.0003 (6)
N2	0.0513 (12)	0.086 (2)	0.0878 (18)	0.0020 (12)	0.0144 (13)	−0.0067 (15)
O1	0.0771 (11)	0.0426 (10)	0.0421 (8)	−0.0010 (8)	0.0268 (8)	0.0095 (7)
O2	0.0541 (8)	0.0308 (8)	0.0326 (7)	0.0043 (7)	0.0159 (6)	0.0036 (6)
O3	0.0523 (10)	0.0481 (10)	0.0333 (8)	−0.0011 (8)	0.0076 (8)	−0.0093 (8)
O4	0.0761 (14)	0.0955 (19)	0.0962 (16)	−0.0040 (12)	0.0309 (13)	−0.0163 (15)
C1	0.0444 (10)	0.0296 (10)	0.0276 (9)	−0.0021 (8)	0.0029 (8)	0.0007 (7)
C2	0.0577 (12)	0.0337 (12)	0.0354 (11)	−0.0008 (9)	0.0010 (10)	0.0069 (9)
C3	0.0537 (13)	0.0303 (12)	0.0470 (13)	0.0052 (9)	−0.0023 (11)	0.0061 (9)
C4	0.0413 (11)	0.0306 (11)	0.0462 (12)	0.0043 (9)	−0.0018 (10)	−0.0038 (9)
C5	0.0508 (13)	0.0368 (14)	0.0676 (17)	0.0129 (10)	0.0069 (13)	−0.0032 (11)
C6	0.0565 (14)	0.0514 (15)	0.0673 (17)	0.0140 (12)	0.0190 (13)	−0.0123 (13)
C7	0.0612 (14)	0.0559 (16)	0.0517 (13)	0.0083 (12)	0.0182 (12)	−0.0024 (12)
C8	0.0483 (12)	0.0388 (12)	0.0412 (11)	0.0062 (9)	0.0087 (10)	−0.0001 (9)
C9	0.0488 (11)	0.0328 (11)	0.0292 (9)	−0.0041 (9)	0.0066 (9)	−0.0017 (8)
C10	0.0381 (10)	0.0309 (11)	0.0345 (10)	0.0015 (8)	0.0004 (9)	−0.0042 (8)
C11	0.113 (3)	0.203 (7)	0.100 (3)	0.005 (4)	0.016 (3)	−0.038 (4)
C12	0.065 (2)	0.115 (3)	0.153 (4)	−0.028 (2)	−0.001 (2)	0.017 (3)
C13	0.0485 (14)	0.063 (2)	0.121 (3)	0.0025 (13)	0.0134 (17)	−0.0168 (19)

Geometric parameters (Å, º)

Ni1—O2	1.9985 (15)	C3—C4	1.404 (3)
Ni1—O2^i	1.9985 (15)	C3—H3	0.9300
Ni1—O3^i	2.0954 (17)	C4—C10	1.417 (3)
Ni1—O3	2.0954 (17)	C4—C5	1.417 (3)
Ni1—N1	2.1625 (17)	C5—C6	1.341 (4)
Ni1—N1^i	2.1625 (17)	C5—H5	0.9300
N1—C1	1.319 (3)	C6—C7	1.404 (4)
N1—C10	1.379 (3)	C6—H6	0.9300
N2—C13	1.315 (4)	C7—C8	1.374 (3)
N2—C12	1.426 (4)	C7—H7	0.9300
N2—C11	1.446 (5)	C8—C10	1.402 (3)
O1—C9	1.230 (3)	C8—H8	0.9300
O2—C9	1.263 (3)	C11—H11A	0.9600
O3—H10	0.80 (3)	C11—H11B	0.9600
O3—H9	0.78 (3)	C11—H11C	0.9600
O4—C13	1.240 (4)	C12—H12A	0.9600
C1—C2	1.404 (3)	C12—H12B	0.9600
C1—C9	1.520 (3)	C12—H12C	0.9600
C2—C3	1.360 (3)	C13—H13	0.9300
C2—H2	0.9300
O2—Ni1—O2^i	180.00 (11)	C3—C4—C5	122.7 (2)
O2—Ni1—O3^i	88.69 (7)	C10—C4—C5	118.4 (2)
O2^i—Ni1—O3^i	91.31 (7)	C6—C5—C4	121.2 (2)
O2—Ni1—O3	91.31 (7)	C6—C5—H5	119.4
O2^i—Ni1—O3	88.69 (7)	C4—C5—H5	119.4
O3^i—Ni1—O3	180.00 (14)	C5—C6—C7	120.5 (2)
O2—Ni1—N1	79.17 (6)	C5—C6—H6	119.7
O2^i—Ni1—N1	100.83 (6)	C7—C6—H6	119.7
O3^i—Ni1—N1	88.32 (7)	C8—C7—C6	120.3 (2)
O3—Ni1—N1	91.68 (7)	C8—C7—H7	119.9
O2—Ni1—N1^i	100.83 (6)	C6—C7—H7	119.9
O2^i—Ni1—N1^i	79.17 (6)	C7—C8—C10	120.2 (2)
O3^i—Ni1—N1^i	91.68 (7)	C7—C8—H8	119.9
O3—Ni1—N1^i	88.32 (7)	C10—C8—H8	119.9
N1—Ni1—N1^i	180.00 (11)	O1—C9—O2	125.2 (2)
C1—N1—C10	118.00 (17)	O1—C9—C1	118.99 (19)
C1—N1—Ni1	110.22 (13)	O2—C9—C1	115.81 (17)
C10—N1—Ni1	131.71 (13)	N1—C10—C8	119.76 (18)
C13—N2—C12	122.9 (3)	N1—C10—C4	120.92 (19)
C13—N2—C11	120.1 (3)	C8—C10—C4	119.30 (19)
C12—N2—C11	116.9 (4)	N2—C11—H11A	109.5
C9—O2—Ni1	118.19 (13)	N2—C11—H11B	109.5
Ni1—O3—H10	119.5 (18)	H11A—C11—H11B	109.5
Ni1—O3—H9	121 (2)	N2—C11—H11C	109.5
H10—O3—H9	106 (3)	H11A—C11—H11C	109.5
N1—C1—C2	123.9 (2)	H11B—C11—H11C	109.5
N1—C1—C9	116.26 (17)	N2—C12—H12A	109.5
C2—C1—C9	119.81 (18)	N2—C12—H12B	109.5
C3—C2—C1	119.1 (2)	H12A—C12—H12B	109.5
C3—C2—H2	120.5	N2—C12—H12C	109.5
C1—C2—H2	120.5	H12A—C12—H12C	109.5
C2—C3—C4	119.2 (2)	H12B—C12—H12C	109.5
C2—C3—H3	120.4	O4—C13—N2	125.0 (3)
C4—C3—H3	120.4	O4—C13—H13	117.5
C3—C4—C10	118.8 (2)	N2—C13—H13	117.5
O2—Ni1—N1—C1	5.23 (13)	C10—C4—C5—C6	2.1 (3)
O2^i—Ni1—N1—C1	−174.77 (13)	C4—C5—C6—C7	−2.0 (4)
O3^i—Ni1—N1—C1	−83.76 (14)	C5—C6—C7—C8	0.0 (4)
O3—Ni1—N1—C1	96.24 (14)	C6—C7—C8—C10	2.0 (4)
O2—Ni1—N1—C10	−178.11 (17)	Ni1—O2—C9—O1	−178.02 (16)
O2^i—Ni1—N1—C10	1.89 (17)	Ni1—O2—C9—C1	2.5 (2)
O3^i—Ni1—N1—C10	92.91 (16)	N1—C1—C9—O1	−177.03 (18)
O3—Ni1—N1—C10	−87.09 (16)	C2—C1—C9—O1	1.7 (3)
O3^i—Ni1—O2—C9	84.32 (15)	N1—C1—C9—O2	2.5 (3)
O3—Ni1—O2—C9	−95.68 (15)	C2—C1—C9—O2	−178.76 (18)
N1—Ni1—O2—C9	−4.22 (14)	C1—N1—C10—C8	−175.18 (18)
N1^i—Ni1—O2—C9	175.78 (14)	Ni1—N1—C10—C8	8.4 (3)
C10—N1—C1—C2	−1.4 (3)	C1—N1—C10—C4	3.2 (3)
Ni1—N1—C1—C2	175.76 (15)	Ni1—N1—C10—C4	−173.23 (13)
C10—N1—C1—C9	177.27 (15)	C7—C8—C10—N1	176.60 (18)
Ni1—N1—C1—C9	−5.6 (2)	C7—C8—C10—C4	−1.8 (3)
N1—C1—C2—C3	−1.6 (3)	C3—C4—C10—N1	−2.1 (3)
C9—C1—C2—C3	179.76 (18)	C5—C4—C10—N1	−178.57 (19)
C1—C2—C3—C4	2.7 (3)	C3—C4—C10—C8	176.3 (2)
C2—C3—C4—C10	−1.0 (3)	C5—C4—C10—C8	−0.2 (3)
C2—C3—C4—C5	175.4 (2)	C12—N2—C13—O4	−0.3 (5)
C3—C4—C5—C6	−174.2 (2)	C11—N2—C13—O4	178.4 (4)

Symmetry code: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H10···O1^ii	0.80 (3)	1.96 (3)	2.761 (2)	175 (3)
O3—H9···O4^iii	0.78 (3)	2.01 (3)	2.795 (3)	175 (3)
C13—H13···O2^iii	0.93	2.41	3.160 (3)	138
C2—H2···O2^iv	0.93	2.58	3.350 (3)	141
C3—H3···O1^iv	0.93	2.54	3.263 (3)	135

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