



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809055408/hb5292sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809055408/hb5292Isup2.hkl |
CCDC reference: 764984
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.007 Å
- R factor = 0.066
- wR factor = 0.199
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.67 Ratio PLAT230_ALERT_2_B Hirshfeld Test Diff for C9 -- C10 .. 13.88 su PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 122.00 A 3 PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density -2.81 eA-3 PLAT924_ALERT_1_B The Reported and Calculated Rho(min) Differ by . 2.43 eA-3 PLAT926_ALERT_1_B Reported and Calculated R1 * 100.0 Differ by . -1.83 PLAT927_ALERT_1_B Reported and Calculated wR2 * 100.0 Differ by . -4.91 PLAT928_ALERT_1_B Reported and Calculated S value Differ by . -0.25
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.30 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.24 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 7 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.597 93
Alert level G PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large.. 0.12 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 8 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 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
A mixture of Ni(CH3COO)2.4H2O (0.063 g, 0.25 mmol), Hppa (0.15 g, 0.5 mmol), sodium hydroxide (0.04 g, 1 mmol) and water (15 ml) was stirred for 30 min in air. The mixture was then transferred to a 25 ml Teflon-lined hydrothermal bomb. The bomb was kept at 443 K for 72 h under autogenous pressure. Upon cooling, green prisms of (I) were obtained from the reaction mixture.
The carbon-bound H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) = 1.2Ueq(C). The H on Nitrogen atoms were located in a difference Fourier map, and were refined with a distance restraint of N—H = 0.86 (1) /%A and with Uiso(H) = 1.2Ueq(N).
Pipemidic acid (Hppa, C14H16N5O3, 8-Ethyl-5,8-dihydro-5-oxo-2- (1-piperazinyl)-pyrido(2,3-d)-pyrimidine-6-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). The manganese, cobalt and zinc complexes of the ppa anion have been reported (Huang et al., 2008; Xu et al. 2009; Qi Xu et al.2009). The title nickel(II) complex, (I), is reported here (Fig. 1).
The nickel(II) atom is coordinated by four oxygen atoms and two N atoms from four ppa ligands (two monodentate-N and two O,O-bidentate) to form a square grid propagating in (Fig. 2).
For manganese, cobalt and zinc complexes of the ppa anion, see: Huang et al. (2008); Xu et al. (2009); Qi et al. (2009), respectively. For background to the medicinal uses of pipemidic acid, see: Mizuki et al. (1996).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Ni(C14H16N5O3)2] | F(000) = 692 |
Mr = 663.35 | Dx = 1.378 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3258 reflections |
a = 6.1249 (6) Å | θ = 2.5–28.3° |
b = 21.250 (2) Å | µ = 0.66 mm−1 |
c = 12.5511 (12) Å | T = 296 K |
β = 101.846 (2)° | Prism, green |
V = 1598.8 (3) Å3 | 0.43 × 0.28 × 0.22 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 2762 independent reflections |
Radiation source: fine-focus sealed tube | 2389 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 25.1°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −7→7 |
Tmin = 0.764, Tmax = 0.868 | k = −25→23 |
7593 measured reflections | l = −14→9 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H-atom parameters not refined |
S = 1.00 | w = 1/[σ2(Fo2) + (0.122P)2 + 2.8827P] where P = (Fo2 + 2Fc2)/3 |
2762 reflections | (Δ/σ)max = 0.007 |
209 parameters | Δρmax = 0.89 e Å−3 |
1 restraint | Δρmin = −0.39 e Å−3 |
[Ni(C14H16N5O3)2] | V = 1598.8 (3) Å3 |
Mr = 663.35 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.1249 (6) Å | µ = 0.66 mm−1 |
b = 21.250 (2) Å | T = 296 K |
c = 12.5511 (12) Å | 0.43 × 0.28 × 0.22 mm |
β = 101.846 (2)° |
Bruker APEXII CCD diffractometer | 2762 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2389 reflections with I > 2σ(I) |
Tmin = 0.764, Tmax = 0.868 | Rint = 0.034 |
7593 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 1 restraint |
wR(F2) = 0.199 | H-atom parameters not refined |
S = 1.00 | Δρmax = 0.89 e Å−3 |
2762 reflections | Δρmin = −0.39 e Å−3 |
209 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.0219 (3) | |
C1 | 0.7141 (7) | 0.47283 (19) | 0.3080 (4) | 0.0293 (9) | |
C2 | 0.5607 (7) | 0.41749 (19) | 0.2771 (3) | 0.0310 (9) | |
C3 | 0.3908 (6) | 0.39745 (18) | 0.3348 (3) | 0.0250 (8) | |
C4 | 0.2685 (7) | 0.34232 (19) | 0.2900 (3) | 0.0287 (9) | |
C5 | 0.0880 (8) | 0.3175 (2) | 0.3310 (4) | 0.0380 (11) | |
H5 | 0.0416 | 0.3397 | 0.3863 | 0.046* | |
C6 | 0.0596 (7) | 0.2340 (2) | 0.2186 (4) | 0.0310 (9) | |
C7 | 0.3168 (7) | 0.3083 (2) | 0.2024 (4) | 0.0333 (10) | |
C8 | 0.5934 (9) | 0.3829 (2) | 0.1908 (4) | 0.0448 (12) | |
H8 | 0.7017 | 0.3972 | 0.1544 | 0.054* | |
C9 | 0.5451 (11) | 0.2956 (3) | 0.0587 (6) | 0.0655 (18) | |
H9A | 0.7027 | 0.3014 | 0.0599 | 0.079* | |
H9B | 0.5179 | 0.2510 | 0.0652 | 0.079* | |
C10 | 0.4140 (17) | 0.3190 (6) | −0.0446 (8) | 0.0426 (8) | |
H10A | 0.2601 | 0.3080 | −0.0501 | 0.168* | |
H10B | 0.4681 | 0.3005 | −0.1039 | 0.168* | |
H10C | 0.4278 | 0.3640 | −0.0473 | 0.168* | |
C11 | −0.1716 (9) | 0.1431 (2) | 0.2519 (4) | 0.0462 (13) | |
H11A | −0.2457 | 0.1731 | 0.2908 | 0.055* | |
H11B | −0.0778 | 0.1164 | 0.3051 | 0.055* | |
C12 | −0.3438 (8) | 0.1034 (2) | 0.1784 (4) | 0.0375 (10) | |
H12A | −0.4224 | 0.0785 | 0.2233 | 0.045* | |
H12B | −0.4517 | 0.1311 | 0.1343 | 0.045* | |
C13 | 0.0646 (7) | 0.1360 (2) | 0.1181 (4) | 0.0330 (10) | |
H13A | 0.1711 | 0.1080 | 0.1622 | 0.040* | |
H13B | 0.1435 | 0.1611 | 0.0735 | 0.040* | |
C14 | −0.1164 (7) | 0.0976 (2) | 0.0452 (4) | 0.0297 (9) | |
H14A | −0.2129 | 0.1259 | −0.0039 | 0.036* | |
H14B | −0.0469 | 0.0694 | 0.0013 | 0.036* | |
H5N | −0.163 (7) | 0.035 (2) | 0.152 (3) | 0.044* | |
N1 | 0.4839 (7) | 0.3299 (2) | 0.1527 (3) | 0.0454 (11) | |
N2 | 0.2161 (6) | 0.25401 (17) | 0.1666 (3) | 0.0354 (9) | |
N3 | −0.0183 (7) | 0.26577 (19) | 0.2969 (4) | 0.0427 (10) | |
N4 | −0.0326 (6) | 0.17705 (17) | 0.1881 (3) | 0.0327 (8) | |
N5 | −0.2530 (5) | 0.06053 (15) | 0.1053 (3) | 0.0262 (7) | |
O1 | 0.3477 (5) | 0.42282 (13) | 0.4188 (2) | 0.0288 (7) | |
O2 | 0.6982 (5) | 0.50474 (11) | 0.3906 (2) | 0.0270 (7) | |
O3 | 0.8546 (7) | 0.4840 (2) | 0.2525 (3) | 0.0579 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0256 (4) | 0.0139 (4) | 0.0257 (4) | −0.0008 (2) | 0.0040 (3) | −0.0028 (3) |
C1 | 0.032 (2) | 0.022 (2) | 0.034 (2) | −0.0029 (17) | 0.0055 (18) | −0.0007 (17) |
C2 | 0.041 (2) | 0.022 (2) | 0.031 (2) | −0.0069 (17) | 0.0088 (18) | −0.0052 (17) |
C3 | 0.0291 (19) | 0.0178 (18) | 0.026 (2) | −0.0008 (15) | 0.0020 (16) | −0.0002 (16) |
C4 | 0.034 (2) | 0.023 (2) | 0.030 (2) | −0.0027 (17) | 0.0072 (17) | −0.0047 (17) |
C5 | 0.040 (2) | 0.032 (2) | 0.046 (3) | −0.0112 (19) | 0.019 (2) | −0.019 (2) |
C6 | 0.032 (2) | 0.024 (2) | 0.038 (2) | −0.0061 (17) | 0.0082 (18) | −0.0090 (18) |
C7 | 0.041 (2) | 0.028 (2) | 0.034 (2) | −0.0039 (18) | 0.0117 (19) | −0.0074 (18) |
C8 | 0.059 (3) | 0.037 (3) | 0.043 (3) | −0.017 (2) | 0.022 (2) | −0.012 (2) |
C9 | 0.077 (4) | 0.060 (4) | 0.068 (4) | −0.025 (3) | 0.034 (3) | −0.018 (3) |
C10 | 0.0396 (18) | 0.047 (2) | 0.0409 (17) | 0.0122 (15) | 0.0083 (14) | 0.0059 (15) |
C11 | 0.052 (3) | 0.041 (3) | 0.053 (3) | −0.025 (2) | 0.028 (2) | −0.021 (2) |
C12 | 0.039 (2) | 0.031 (2) | 0.045 (3) | −0.0097 (19) | 0.015 (2) | −0.011 (2) |
C13 | 0.029 (2) | 0.029 (2) | 0.045 (2) | −0.0055 (17) | 0.0152 (19) | −0.0153 (19) |
C14 | 0.032 (2) | 0.0219 (19) | 0.037 (2) | −0.0034 (16) | 0.0120 (18) | −0.0042 (17) |
N1 | 0.061 (3) | 0.040 (2) | 0.042 (2) | −0.025 (2) | 0.026 (2) | −0.0145 (18) |
N2 | 0.047 (2) | 0.0271 (18) | 0.035 (2) | −0.0156 (16) | 0.0169 (17) | −0.0112 (16) |
N3 | 0.044 (2) | 0.030 (2) | 0.057 (3) | −0.0140 (17) | 0.0198 (19) | −0.0192 (19) |
N4 | 0.0348 (18) | 0.0239 (18) | 0.042 (2) | −0.0081 (15) | 0.0143 (16) | −0.0121 (16) |
N5 | 0.0275 (17) | 0.0193 (16) | 0.0303 (18) | −0.0026 (13) | 0.0020 (14) | −0.0004 (14) |
O1 | 0.0317 (15) | 0.0215 (14) | 0.0351 (16) | −0.0043 (11) | 0.0111 (12) | −0.0069 (12) |
O2 | 0.0329 (16) | 0.0184 (14) | 0.0298 (16) | 0.0003 (11) | 0.0066 (12) | −0.0026 (11) |
O3 | 0.069 (3) | 0.061 (2) | 0.055 (2) | −0.037 (2) | 0.040 (2) | −0.026 (2) |
Ni1—O2i | 2.013 (3) | C9—C10 | 1.464 (12) |
Ni1—O2 | 2.013 (3) | C9—N1 | 1.498 (7) |
Ni1—O1i | 2.051 (3) | C9—H9A | 0.9700 |
Ni1—O1 | 2.051 (3) | C9—H9B | 0.9700 |
Ni1—N5ii | 2.207 (3) | C10—H10A | 0.9600 |
Ni1—N5iii | 2.207 (3) | C10—H10B | 0.9600 |
C1—O3 | 1.236 (6) | C10—H10C | 0.9600 |
C1—O2 | 1.260 (5) | C11—N4 | 1.472 (6) |
C1—C2 | 1.505 (6) | C11—C12 | 1.509 (6) |
C2—C8 | 1.358 (6) | C11—H11A | 0.9700 |
C2—C3 | 1.448 (6) | C11—H11B | 0.9700 |
C3—O1 | 1.260 (5) | C12—N5 | 1.480 (6) |
C3—C4 | 1.441 (6) | C12—H12A | 0.9700 |
C4—C7 | 1.398 (6) | C12—H12B | 0.9700 |
C4—C5 | 1.413 (6) | C13—N4 | 1.450 (5) |
C5—N3 | 1.305 (6) | C13—C14 | 1.522 (6) |
C5—H5 | 0.9300 | C13—H13A | 0.9700 |
C6—N2 | 1.334 (6) | C13—H13B | 0.9700 |
C6—N4 | 1.357 (5) | C14—N5 | 1.467 (5) |
C6—N3 | 1.357 (6) | C14—H14A | 0.9700 |
C7—N2 | 1.341 (6) | C14—H14B | 0.9700 |
C7—N1 | 1.382 (6) | N5—Ni1iv | 2.207 (3) |
C8—N1 | 1.348 (6) | N5—H5N | 0.90 (4) |
C8—H8 | 0.9300 | ||
O2i—Ni1—O2 | 180.0 | C9—C10—H10B | 109.5 |
O2i—Ni1—O1i | 88.73 (11) | H10A—C10—H10B | 109.5 |
O2—Ni1—O1i | 91.27 (11) | C9—C10—H10C | 109.5 |
O2i—Ni1—O1 | 91.27 (11) | H10A—C10—H10C | 109.5 |
O2—Ni1—O1 | 88.73 (11) | H10B—C10—H10C | 109.5 |
O1i—Ni1—O1 | 180.0 | N4—C11—C12 | 110.6 (4) |
O2i—Ni1—N5ii | 90.14 (12) | N4—C11—H11A | 109.5 |
O2—Ni1—N5ii | 89.86 (12) | C12—C11—H11A | 109.5 |
O1i—Ni1—N5ii | 91.00 (11) | N4—C11—H11B | 109.5 |
O1—Ni1—N5ii | 89.00 (11) | C12—C11—H11B | 109.5 |
O2i—Ni1—N5iii | 89.86 (12) | H11A—C11—H11B | 108.1 |
O2—Ni1—N5iii | 90.14 (12) | N5—C12—C11 | 114.8 (4) |
O1i—Ni1—N5iii | 89.00 (11) | N5—C12—H12A | 108.6 |
O1—Ni1—N5iii | 91.00 (11) | C11—C12—H12A | 108.6 |
N5ii—Ni1—N5iii | 180.0 | N5—C12—H12B | 108.6 |
O3—C1—O2 | 122.8 (4) | C11—C12—H12B | 108.6 |
O3—C1—C2 | 118.4 (4) | H12A—C12—H12B | 107.6 |
O2—C1—C2 | 118.9 (4) | N4—C13—C14 | 110.4 (3) |
C8—C2—C3 | 118.6 (4) | N4—C13—H13A | 109.6 |
C8—C2—C1 | 116.2 (4) | C14—C13—H13A | 109.6 |
C3—C2—C1 | 125.1 (4) | N4—C13—H13B | 109.6 |
O1—C3—C4 | 119.5 (4) | C14—C13—H13B | 109.6 |
O1—C3—C2 | 126.1 (4) | H13A—C13—H13B | 108.1 |
C4—C3—C2 | 114.4 (4) | N5—C14—C13 | 113.6 (4) |
C7—C4—C5 | 113.6 (4) | N5—C14—H14A | 108.8 |
C7—C4—C3 | 123.4 (4) | C13—C14—H14A | 108.8 |
C5—C4—C3 | 122.9 (4) | N5—C14—H14B | 108.8 |
N3—C5—C4 | 124.7 (4) | C13—C14—H14B | 108.8 |
N3—C5—H5 | 117.6 | H14A—C14—H14B | 107.7 |
C4—C5—H5 | 117.6 | C8—N1—C7 | 118.6 (4) |
N2—C6—N4 | 116.5 (4) | C8—N1—C9 | 119.9 (4) |
N2—C6—N3 | 126.2 (4) | C7—N1—C9 | 121.5 (4) |
N4—C6—N3 | 117.4 (4) | C6—N2—C7 | 115.9 (4) |
N2—C7—N1 | 117.8 (4) | C5—N3—C6 | 115.5 (4) |
N2—C7—C4 | 123.5 (4) | C6—N4—C13 | 120.5 (4) |
N1—C7—C4 | 118.6 (4) | C6—N4—C11 | 122.5 (4) |
N1—C8—C2 | 126.3 (5) | C13—N4—C11 | 113.0 (3) |
N1—C8—H8 | 116.9 | C14—N5—C12 | 108.4 (3) |
C2—C8—H8 | 116.9 | C14—N5—Ni1iv | 113.5 (2) |
C10—C9—N1 | 110.6 (7) | C12—N5—Ni1iv | 115.6 (2) |
C10—C9—H9A | 109.5 | C14—N5—H5N | 109 (3) |
N1—C9—H9A | 109.5 | C12—N5—H5N | 103 (4) |
C10—C9—H9B | 109.5 | Ni1iv—N5—H5N | 107 (3) |
N1—C9—H9B | 109.5 | C3—O1—Ni1 | 127.3 (3) |
H9A—C9—H9B | 108.1 | C1—O2—Ni1 | 134.0 (3) |
C9—C10—H10A | 109.5 | ||
O3—C1—C2—C8 | 1.5 (7) | N3—C6—N2—C7 | 5.9 (7) |
O2—C1—C2—C8 | −176.7 (4) | N1—C7—N2—C6 | 178.4 (4) |
O3—C1—C2—C3 | 178.7 (4) | C4—C7—N2—C6 | 1.4 (7) |
O2—C1—C2—C3 | 0.6 (6) | C4—C5—N3—C6 | 2.0 (8) |
C8—C2—C3—O1 | 176.7 (4) | N2—C6—N3—C5 | −7.5 (8) |
C1—C2—C3—O1 | −0.5 (7) | N4—C6—N3—C5 | 174.0 (4) |
C8—C2—C3—C4 | −1.8 (6) | N2—C6—N4—C13 | 11.1 (6) |
C1—C2—C3—C4 | −178.9 (4) | N3—C6—N4—C13 | −170.2 (4) |
O1—C3—C4—C7 | −174.8 (4) | N2—C6—N4—C11 | 167.2 (4) |
C2—C3—C4—C7 | 3.8 (6) | N3—C6—N4—C11 | −14.2 (7) |
O1—C3—C4—C5 | 5.1 (6) | C14—C13—N4—C6 | −147.5 (4) |
C2—C3—C4—C5 | −176.4 (4) | C14—C13—N4—C11 | 54.4 (5) |
C7—C4—C5—N3 | 4.1 (7) | C12—C11—N4—C6 | 149.6 (4) |
C3—C4—C5—N3 | −175.8 (5) | C12—C11—N4—C13 | −52.7 (6) |
C5—C4—C7—N2 | −5.8 (7) | C13—C14—N5—C12 | 54.2 (5) |
C3—C4—C7—N2 | 174.0 (4) | C13—C14—N5—Ni1iv | −176.1 (3) |
C5—C4—C7—N1 | 177.2 (4) | C11—C12—N5—C14 | −53.0 (5) |
C3—C4—C7—N1 | −2.9 (7) | C11—C12—N5—Ni1iv | 178.4 (3) |
C3—C2—C8—N1 | −1.0 (8) | C4—C3—O1—Ni1 | 178.8 (3) |
C1—C2—C8—N1 | 176.4 (5) | C2—C3—O1—Ni1 | 0.4 (6) |
N4—C11—C12—N5 | 52.7 (6) | O2i—Ni1—O1—C3 | 179.7 (3) |
N4—C13—C14—N5 | −56.3 (5) | O2—Ni1—O1—C3 | −0.3 (3) |
C2—C8—N1—C7 | 2.0 (8) | N5ii—Ni1—O1—C3 | 89.6 (3) |
C2—C8—N1—C9 | −177.7 (6) | N5iii—Ni1—O1—C3 | −90.4 (3) |
N2—C7—N1—C8 | −177.2 (5) | O3—C1—O2—Ni1 | −178.7 (4) |
C4—C7—N1—C8 | 0.0 (7) | C2—C1—O2—Ni1 | −0.7 (6) |
N2—C7—N1—C9 | 2.6 (8) | O1i—Ni1—O2—C1 | −179.5 (4) |
C4—C7—N1—C9 | 179.8 (5) | O1—Ni1—O2—C1 | 0.5 (4) |
C10—C9—N1—C8 | −89.8 (8) | N5ii—Ni1—O2—C1 | −88.5 (4) |
C10—C9—N1—C7 | 90.4 (7) | N5iii—Ni1—O2—C1 | 91.5 (4) |
N4—C6—N2—C7 | −175.6 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, y+1/2, −z+1/2; (iii) x+1, −y+1/2, z+1/2; (iv) −x, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3v | 0.90 (4) | 2.29 (4) | 3.161 (5) | 163 (5) |
Symmetry code: (v) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C14H16N5O3)2] |
Mr | 663.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 6.1249 (6), 21.250 (2), 12.5511 (12) |
β (°) | 101.846 (2) |
V (Å3) | 1598.8 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.66 |
Crystal size (mm) | 0.43 × 0.28 × 0.22 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.764, 0.868 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7593, 2762, 2389 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.199, 1.00 |
No. of reflections | 2762 |
No. of parameters | 209 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.89, −0.39 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Ni1—O2 | 2.013 (3) | Ni1—N5i | 2.207 (3) |
Ni1—O1 | 2.051 (3) |
Symmetry code: (i) −x, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3ii | 0.90 (4) | 2.29 (4) | 3.161 (5) | 163 (5) |
Symmetry code: (ii) −x+1, y−1/2, −z+1/2. |
Pipemidic acid (Hppa, C14H16N5O3, 8-Ethyl-5,8-dihydro-5-oxo-2- (1-piperazinyl)-pyrido(2,3-d)-pyrimidine-6-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). The manganese, cobalt and zinc complexes of the ppa anion have been reported (Huang et al., 2008; Xu et al. 2009; Qi Xu et al.2009). The title nickel(II) complex, (I), is reported here (Fig. 1).
The nickel(II) atom is coordinated by four oxygen atoms and two N atoms from four ppa ligands (two monodentate-N and two O,O-bidentate) to form a square grid propagating in (Fig. 2).