Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052750/dn2252sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052750/dn2252Isup2.hkl |
CCDC reference: 667234
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.098
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 1.90
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 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 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 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The ligand N3-salicyloylpyridine-2-carboxamidrazonato (Hspa) was synthesized according to literature (Van Koningsbruggen et al., 1993, 1995). [Zn(C13H11N4O2)2] was synthesized by adding ligand (0.0256 g, 0.10 mmol) and Et3N (0.010 g, 0.1 mmol) in 1 ml DMSO to a solution of Zn(acac)2 (0.0263 g, 0.10 mmol) in CH2Cl2 (4 ml). The compound crystallized upon evaporation of the solvent at room temperature after a few days.
H atoms of the hydroxyls were located in a difference synthesis and refined isotropically, and with Uiso(H) = 1.2Ueq(O). Other H atoms were positioned geometrically and refined using a riding mode, with Uiso(H) = 1.2 times Ueq(C, N).
The N3-salicyloylpyridine-2-carboxamidrazonato ligand (abbreviated as Hspa) has several potential donor atoms and can occur in different chemical and structural conformations. In the Copper(II) coordination compound containing the dehydrogenated spa ligand (Van Koningsbruggen et al., 1993, 1995), this spa ligand is fairly planar, whereas in the title complex it is slighted bent around the central Zn—N bonds, with a dihedral angle of 21.15 (6)° between the two aromatic rings (Fig. 1).
There are two intramolecular O—H···N hydrogen bonds involving the hydroxyl groups, whereas intermolecular N—H···O hydrogen bonds connect the molecules to build up a chain parallel to the b axis (Fig. 2).
For a related structure, see: Van Koningsbruggen et al. (1993, 1995).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
[Zn(C13H11N4O2)2] | F(000) = 1184 |
Mr = 575.89 | Dx = 1.529 Mg m−3 |
Monoclinic, P2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yc | Cell parameters from 10850 reflections |
a = 10.7704 (9) Å | θ = 2.4–28.2° |
b = 13.1196 (11) Å | µ = 1.03 mm−1 |
c = 19.6427 (14) Å | T = 173 K |
β = 115.630 (4)° | Block, yellow |
V = 2502.5 (4) Å3 | 0.45 × 0.42 × 0.35 mm |
Z = 4 |
Bruker APEX CCD diffractometer | 4662 independent reflections |
Radiation source: sealed tube | 4269 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 25.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −13→11 |
Tmin = 0.636, Tmax = 0.700 | k = −13→15 |
13224 measured reflections | l = −23→23 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0553P)2 + 1.8417P] where P = (Fo2 + 2Fc2)/3 |
4662 reflections | (Δ/σ)max = 0.002 |
354 parameters | Δρmax = 0.85 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
[Zn(C13H11N4O2)2] | V = 2502.5 (4) Å3 |
Mr = 575.89 | Z = 4 |
Monoclinic, P2/c | Mo Kα radiation |
a = 10.7704 (9) Å | µ = 1.03 mm−1 |
b = 13.1196 (11) Å | T = 173 K |
c = 19.6427 (14) Å | 0.45 × 0.42 × 0.35 mm |
β = 115.630 (4)° |
Bruker APEX CCD diffractometer | 4662 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 4269 reflections with I > 2σ(I) |
Tmin = 0.636, Tmax = 0.700 | Rint = 0.023 |
13224 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.85 e Å−3 |
4662 reflections | Δρmin = −0.47 e Å−3 |
354 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 | ||
Zn1 | 0.50740 (2) | 0.755008 (16) | 0.997968 (12) | 0.02136 (10) | |
O1 | 0.65569 (16) | 0.92559 (12) | 1.27605 (8) | 0.0318 (3) | |
H1 | 0.5991 | 0.9209 | 1.2304 | 0.048* | |
O2 | 0.65510 (14) | 0.71793 (11) | 1.11148 (8) | 0.0233 (3) | |
O3 | 0.66246 (17) | 0.57460 (12) | 0.79709 (9) | 0.0361 (4) | |
H3C | 0.6069 | 0.5801 | 0.8165 | 0.054* | |
O4 | 0.66491 (14) | 0.78488 (10) | 0.96013 (8) | 0.0234 (3) | |
N1 | 0.55574 (16) | 0.85711 (12) | 1.14099 (9) | 0.0225 (3) | |
N2 | 0.47785 (16) | 0.86238 (12) | 1.06345 (9) | 0.0214 (3) | |
N3 | 0.36365 (19) | 1.00564 (12) | 1.07950 (10) | 0.0261 (4) | |
H3A | 0.4037 | 1.0007 | 1.1291 | 0.031* | |
H3B | 0.3045 | 1.0551 | 1.0576 | 0.031* | |
N4 | 0.34997 (16) | 0.86802 (13) | 0.91667 (9) | 0.0238 (4) | |
N5 | 0.56026 (17) | 0.64891 (13) | 0.88078 (9) | 0.0243 (4) | |
N6 | 0.47942 (16) | 0.64650 (13) | 0.91961 (9) | 0.0225 (3) | |
N7 | 0.3818 (2) | 0.49273 (13) | 0.85983 (11) | 0.0301 (4) | |
H7A | 0.4241 | 0.4949 | 0.8303 | 0.036* | |
H7B | 0.3268 | 0.4414 | 0.8565 | 0.036* | |
N8 | 0.35017 (17) | 0.64502 (13) | 1.00461 (9) | 0.0251 (4) | |
C1 | 0.7504 (2) | 0.85039 (16) | 1.29318 (11) | 0.0268 (4) | |
C2 | 0.7468 (2) | 0.77696 (16) | 1.23975 (11) | 0.0248 (4) | |
C3 | 0.8479 (2) | 0.70121 (19) | 1.26353 (13) | 0.0337 (5) | |
H3 | 0.8458 | 0.6502 | 1.2287 | 0.040* | |
C4 | 0.9503 (2) | 0.6987 (2) | 1.33609 (14) | 0.0416 (6) | |
H4 | 1.0176 | 0.6461 | 1.3509 | 0.050* | |
C5 | 0.9556 (2) | 0.7724 (2) | 1.38756 (13) | 0.0384 (6) | |
H5 | 1.0278 | 0.7715 | 1.4373 | 0.046* | |
C6 | 0.8557 (2) | 0.84767 (19) | 1.36664 (12) | 0.0342 (5) | |
H6 | 0.8588 | 0.8976 | 1.4023 | 0.041* | |
C7 | 0.64676 (19) | 0.78135 (15) | 1.15900 (11) | 0.0207 (4) | |
C8 | 0.39280 (19) | 0.93784 (14) | 1.03738 (11) | 0.0205 (4) | |
C9 | 0.31880 (18) | 0.94341 (14) | 0.95347 (11) | 0.0202 (4) | |
C10 | 0.2237 (2) | 1.01911 (16) | 0.91557 (12) | 0.0253 (4) | |
H10 | 0.2038 | 1.0718 | 0.9426 | 0.030* | |
C11 | 0.1584 (2) | 1.01588 (17) | 0.83733 (12) | 0.0297 (5) | |
H11 | 0.0932 | 1.0668 | 0.8099 | 0.036* | |
C12 | 0.1884 (2) | 0.93879 (17) | 0.79973 (12) | 0.0314 (5) | |
H12 | 0.1438 | 0.9350 | 0.7462 | 0.038* | |
C13 | 0.2853 (2) | 0.86639 (17) | 0.84151 (11) | 0.0287 (5) | |
H13 | 0.3065 | 0.8133 | 0.8154 | 0.034* | |
C14 | 0.7624 (2) | 0.64543 (17) | 0.82713 (12) | 0.0298 (5) | |
C15 | 0.7599 (2) | 0.72169 (16) | 0.87768 (11) | 0.0248 (4) | |
C16 | 0.8671 (2) | 0.79311 (17) | 0.90454 (12) | 0.0299 (5) | |
H16 | 0.8650 | 0.8461 | 0.9370 | 0.036* | |
C17 | 0.9754 (2) | 0.7883 (2) | 0.88506 (14) | 0.0372 (5) | |
H17 | 1.0474 | 0.8372 | 0.9042 | 0.045* | |
C18 | 0.9785 (3) | 0.7114 (2) | 0.83724 (14) | 0.0414 (6) | |
H18 | 1.0543 | 0.7068 | 0.8248 | 0.050* | |
C19 | 0.8724 (3) | 0.6415 (2) | 0.80769 (13) | 0.0382 (5) | |
H19 | 0.8745 | 0.5904 | 0.7739 | 0.046* | |
C20 | 0.6551 (2) | 0.72165 (15) | 0.90799 (11) | 0.0214 (4) | |
C21 | 0.4011 (2) | 0.56730 (15) | 0.90969 (10) | 0.0222 (4) | |
C22 | 0.32611 (19) | 0.56442 (15) | 0.95812 (10) | 0.0207 (4) | |
C23 | 0.2401 (2) | 0.48520 (16) | 0.95648 (12) | 0.0263 (4) | |
H23 | 0.2257 | 0.4289 | 0.9235 | 0.032* | |
C24 | 0.1753 (2) | 0.48959 (17) | 1.00393 (13) | 0.0309 (5) | |
H24 | 0.1152 | 0.4365 | 1.0037 | 0.037* | |
C25 | 0.1992 (2) | 0.57185 (19) | 1.05130 (13) | 0.0358 (5) | |
H25 | 0.1563 | 0.5763 | 1.0845 | 0.043* | |
C26 | 0.2868 (2) | 0.64814 (18) | 1.04985 (13) | 0.0323 (5) | |
H26 | 0.3025 | 0.7051 | 1.0824 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.02212 (15) | 0.02048 (16) | 0.02072 (15) | −0.00079 (8) | 0.00856 (11) | −0.00534 (8) |
O1 | 0.0361 (8) | 0.0338 (8) | 0.0204 (7) | 0.0050 (7) | 0.0075 (6) | −0.0043 (6) |
O2 | 0.0244 (7) | 0.0239 (7) | 0.0199 (7) | 0.0020 (6) | 0.0079 (6) | −0.0023 (5) |
O3 | 0.0447 (9) | 0.0381 (9) | 0.0352 (9) | −0.0083 (7) | 0.0263 (8) | −0.0123 (7) |
O4 | 0.0261 (7) | 0.0216 (7) | 0.0233 (7) | −0.0018 (6) | 0.0115 (6) | −0.0036 (6) |
N1 | 0.0232 (8) | 0.0240 (8) | 0.0166 (8) | 0.0011 (7) | 0.0051 (7) | −0.0021 (6) |
N2 | 0.0208 (8) | 0.0232 (8) | 0.0168 (8) | 0.0000 (6) | 0.0050 (6) | −0.0033 (6) |
N3 | 0.0323 (9) | 0.0242 (9) | 0.0196 (8) | 0.0074 (7) | 0.0092 (7) | 0.0009 (6) |
N4 | 0.0220 (8) | 0.0261 (9) | 0.0214 (8) | −0.0021 (7) | 0.0077 (7) | −0.0036 (7) |
N5 | 0.0280 (9) | 0.0251 (9) | 0.0230 (8) | −0.0030 (7) | 0.0140 (7) | −0.0039 (7) |
N6 | 0.0231 (8) | 0.0245 (9) | 0.0209 (8) | −0.0023 (7) | 0.0105 (7) | −0.0047 (7) |
N7 | 0.0438 (11) | 0.0241 (10) | 0.0300 (10) | −0.0115 (7) | 0.0231 (9) | −0.0086 (7) |
N8 | 0.0235 (8) | 0.0266 (9) | 0.0250 (8) | −0.0014 (7) | 0.0101 (7) | −0.0049 (7) |
C1 | 0.0278 (10) | 0.0298 (11) | 0.0224 (10) | −0.0026 (8) | 0.0106 (8) | 0.0018 (8) |
C2 | 0.0229 (10) | 0.0291 (10) | 0.0216 (10) | −0.0018 (8) | 0.0090 (8) | 0.0012 (8) |
C3 | 0.0299 (11) | 0.0402 (13) | 0.0282 (11) | 0.0074 (10) | 0.0099 (9) | 0.0019 (10) |
C4 | 0.0309 (12) | 0.0556 (16) | 0.0317 (12) | 0.0145 (11) | 0.0072 (10) | 0.0094 (11) |
C5 | 0.0278 (12) | 0.0568 (15) | 0.0207 (11) | −0.0018 (11) | 0.0013 (9) | 0.0074 (10) |
C6 | 0.0346 (11) | 0.0424 (13) | 0.0216 (10) | −0.0064 (10) | 0.0086 (9) | −0.0012 (9) |
C7 | 0.0213 (9) | 0.0211 (9) | 0.0200 (9) | −0.0016 (7) | 0.0091 (8) | −0.0003 (7) |
C8 | 0.0196 (9) | 0.0195 (9) | 0.0222 (9) | −0.0040 (7) | 0.0089 (8) | −0.0019 (7) |
C9 | 0.0165 (8) | 0.0211 (10) | 0.0215 (9) | −0.0039 (7) | 0.0068 (7) | −0.0009 (7) |
C10 | 0.0225 (10) | 0.0240 (10) | 0.0260 (10) | −0.0011 (8) | 0.0072 (8) | −0.0013 (8) |
C11 | 0.0235 (10) | 0.0317 (11) | 0.0262 (11) | −0.0009 (8) | 0.0034 (8) | 0.0053 (9) |
C12 | 0.0281 (10) | 0.0404 (13) | 0.0195 (10) | −0.0055 (9) | 0.0043 (8) | −0.0001 (9) |
C13 | 0.0281 (10) | 0.0338 (12) | 0.0227 (10) | −0.0035 (9) | 0.0096 (8) | −0.0064 (8) |
C14 | 0.0362 (11) | 0.0315 (11) | 0.0258 (10) | 0.0013 (9) | 0.0172 (9) | 0.0022 (9) |
C15 | 0.0289 (10) | 0.0258 (10) | 0.0219 (10) | 0.0018 (8) | 0.0131 (9) | 0.0043 (8) |
C16 | 0.0322 (11) | 0.0308 (12) | 0.0278 (11) | −0.0001 (9) | 0.0139 (9) | 0.0043 (9) |
C17 | 0.0307 (12) | 0.0452 (14) | 0.0377 (13) | −0.0061 (10) | 0.0165 (10) | 0.0057 (11) |
C18 | 0.0376 (13) | 0.0578 (16) | 0.0398 (13) | 0.0034 (12) | 0.0270 (11) | 0.0063 (12) |
C19 | 0.0443 (13) | 0.0442 (14) | 0.0353 (12) | 0.0018 (11) | 0.0259 (11) | −0.0013 (10) |
C20 | 0.0253 (10) | 0.0194 (9) | 0.0191 (9) | 0.0023 (8) | 0.0093 (8) | 0.0018 (7) |
C21 | 0.0229 (9) | 0.0224 (10) | 0.0184 (9) | 0.0014 (7) | 0.0063 (8) | 0.0003 (7) |
C22 | 0.0166 (8) | 0.0234 (10) | 0.0179 (9) | 0.0020 (7) | 0.0036 (7) | 0.0008 (7) |
C23 | 0.0206 (10) | 0.0264 (10) | 0.0279 (11) | −0.0020 (8) | 0.0067 (8) | −0.0019 (8) |
C24 | 0.0229 (10) | 0.0336 (12) | 0.0357 (12) | −0.0032 (8) | 0.0122 (9) | 0.0033 (9) |
C25 | 0.0319 (11) | 0.0438 (14) | 0.0388 (12) | 0.0000 (10) | 0.0220 (10) | −0.0005 (10) |
C26 | 0.0307 (11) | 0.0377 (12) | 0.0322 (11) | −0.0018 (9) | 0.0170 (9) | −0.0085 (9) |
Zn1—N6 | 2.0213 (16) | C4—C5 | 1.383 (4) |
Zn1—N2 | 2.0234 (16) | C4—H4 | 0.9500 |
Zn1—O2 | 2.1611 (14) | C5—C6 | 1.385 (3) |
Zn1—O4 | 2.1622 (14) | C5—H5 | 0.9500 |
Zn1—N8 | 2.2711 (17) | C6—H6 | 0.9500 |
Zn1—N4 | 2.2980 (17) | C8—C9 | 1.490 (3) |
O1—C1 | 1.352 (3) | C9—C10 | 1.389 (3) |
O1—H1 | 0.8400 | C10—C11 | 1.387 (3) |
O2—C7 | 1.282 (2) | C10—H10 | 0.9500 |
O3—C14 | 1.350 (3) | C11—C12 | 1.371 (3) |
O3—H3C | 0.8400 | C11—H11 | 0.9500 |
O4—C20 | 1.286 (2) | C12—C13 | 1.387 (3) |
N1—C7 | 1.332 (2) | C12—H12 | 0.9500 |
N1—N2 | 1.387 (2) | C13—H13 | 0.9500 |
N2—C8 | 1.294 (2) | C14—C19 | 1.394 (3) |
N3—C8 | 1.341 (3) | C14—C15 | 1.418 (3) |
N3—H3A | 0.8800 | C15—C16 | 1.400 (3) |
N3—H3B | 0.8800 | C15—C20 | 1.487 (3) |
N4—C13 | 1.333 (3) | C16—C17 | 1.378 (3) |
N4—C9 | 1.350 (3) | C16—H16 | 0.9500 |
N5—C20 | 1.329 (3) | C17—C18 | 1.389 (4) |
N5—N6 | 1.384 (2) | C17—H17 | 0.9500 |
N6—C21 | 1.299 (3) | C18—C19 | 1.382 (4) |
N7—C21 | 1.336 (3) | C18—H18 | 0.9500 |
N7—H7A | 0.8800 | C19—H19 | 0.9500 |
N7—H7B | 0.8800 | C21—C22 | 1.491 (3) |
N8—C26 | 1.335 (3) | C22—C23 | 1.383 (3) |
N8—C22 | 1.347 (3) | C23—C24 | 1.386 (3) |
C1—C6 | 1.398 (3) | C23—H23 | 0.9500 |
C1—C2 | 1.413 (3) | C24—C25 | 1.375 (3) |
C2—C3 | 1.397 (3) | C24—H24 | 0.9500 |
C2—C7 | 1.484 (3) | C25—C26 | 1.384 (3) |
C3—C4 | 1.374 (3) | C25—H25 | 0.9500 |
C3—H3 | 0.9500 | C26—H26 | 0.9500 |
N6—Zn1—N2 | 164.11 (7) | N1—C7—C2 | 115.06 (17) |
N6—Zn1—O2 | 115.33 (6) | N2—C8—N3 | 125.28 (18) |
N2—Zn1—O2 | 75.46 (6) | N2—C8—C9 | 115.05 (16) |
N6—Zn1—O4 | 75.32 (6) | N3—C8—C9 | 119.59 (17) |
N2—Zn1—O4 | 117.06 (6) | N4—C9—C10 | 122.22 (18) |
O2—Zn1—O4 | 93.36 (5) | N4—C9—C8 | 114.73 (17) |
N6—Zn1—N8 | 74.16 (6) | C10—C9—C8 | 123.05 (18) |
N2—Zn1—N8 | 94.57 (6) | C11—C10—C9 | 118.35 (19) |
O2—Zn1—N8 | 91.84 (6) | C11—C10—H10 | 120.8 |
O4—Zn1—N8 | 148.25 (6) | C9—C10—H10 | 120.8 |
N6—Zn1—N4 | 95.92 (6) | C12—C11—C10 | 119.7 (2) |
N2—Zn1—N4 | 73.79 (6) | C12—C11—H11 | 120.2 |
O2—Zn1—N4 | 148.73 (6) | C10—C11—H11 | 120.2 |
O4—Zn1—N4 | 95.56 (6) | C11—C12—C13 | 118.61 (19) |
N8—Zn1—N4 | 96.06 (6) | C11—C12—H12 | 120.7 |
C1—O1—H1 | 109.5 | C13—C12—H12 | 120.7 |
C7—O2—Zn1 | 110.66 (12) | N4—C13—C12 | 122.9 (2) |
C14—O3—H3C | 109.5 | N4—C13—H13 | 118.5 |
C20—O4—Zn1 | 110.50 (12) | C12—C13—H13 | 118.5 |
C7—N1—N2 | 110.80 (15) | O3—C14—C19 | 117.8 (2) |
C8—N2—N1 | 117.46 (16) | O3—C14—C15 | 122.60 (19) |
C8—N2—Zn1 | 124.05 (13) | C19—C14—C15 | 119.6 (2) |
N1—N2—Zn1 | 118.47 (12) | C16—C15—C14 | 118.28 (19) |
C8—N3—H3A | 120.0 | C16—C15—C20 | 119.61 (19) |
C8—N3—H3B | 120.0 | C14—C15—C20 | 121.86 (19) |
H3A—N3—H3B | 120.0 | C17—C16—C15 | 121.6 (2) |
C13—N4—C9 | 118.23 (18) | C17—C16—H16 | 119.2 |
C13—N4—Zn1 | 129.38 (14) | C15—C16—H16 | 119.2 |
C9—N4—Zn1 | 112.34 (12) | C16—C17—C18 | 119.5 (2) |
C20—N5—N6 | 110.61 (16) | C16—C17—H17 | 120.3 |
C21—N6—N5 | 117.30 (16) | C18—C17—H17 | 120.3 |
C21—N6—Zn1 | 123.41 (13) | C19—C18—C17 | 120.6 (2) |
N5—N6—Zn1 | 118.78 (12) | C19—C18—H18 | 119.7 |
C21—N7—H7A | 120.0 | C17—C18—H18 | 119.7 |
C21—N7—H7B | 120.0 | C18—C19—C14 | 120.4 (2) |
H7A—N7—H7B | 120.0 | C18—C19—H19 | 119.8 |
C26—N8—C22 | 118.13 (18) | C14—C19—H19 | 119.8 |
C26—N8—Zn1 | 128.85 (14) | O4—C20—N5 | 124.56 (18) |
C22—N8—Zn1 | 112.92 (13) | O4—C20—C15 | 120.22 (18) |
O1—C1—C6 | 117.60 (19) | N5—C20—C15 | 115.08 (17) |
O1—C1—C2 | 122.49 (18) | N6—C21—N7 | 125.48 (18) |
C6—C1—C2 | 119.9 (2) | N6—C21—C22 | 114.88 (17) |
C3—C2—C1 | 118.02 (19) | N7—C21—C22 | 119.63 (17) |
C3—C2—C7 | 119.05 (19) | N8—C22—C23 | 122.43 (18) |
C1—C2—C7 | 122.79 (19) | N8—C22—C21 | 114.46 (17) |
C4—C3—C2 | 121.6 (2) | C23—C22—C21 | 123.10 (18) |
C4—C3—H3 | 119.2 | C22—C23—C24 | 118.7 (2) |
C2—C3—H3 | 119.2 | C22—C23—H23 | 120.7 |
C3—C4—C5 | 120.1 (2) | C24—C23—H23 | 120.7 |
C3—C4—H4 | 119.9 | C25—C24—C23 | 119.1 (2) |
C5—C4—H4 | 119.9 | C25—C24—H24 | 120.4 |
C4—C5—C6 | 120.1 (2) | C23—C24—H24 | 120.4 |
C4—C5—H5 | 120.0 | C24—C25—C26 | 118.9 (2) |
C6—C5—H5 | 120.0 | C24—C25—H25 | 120.6 |
C5—C6—C1 | 120.3 (2) | C26—C25—H25 | 120.6 |
C5—C6—H6 | 119.9 | N8—C26—C25 | 122.7 (2) |
C1—C6—H6 | 119.9 | N8—C26—H26 | 118.6 |
O2—C7—N1 | 124.48 (17) | C25—C26—H26 | 118.6 |
O2—C7—C2 | 120.39 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7B···O2i | 0.88 | 2.17 | 2.882 (2) | 138 |
N7—H7A···O3ii | 0.88 | 2.49 | 3.100 (2) | 127 |
N3—H3B···O4iii | 0.88 | 2.18 | 2.837 (2) | 131 |
N3—H3A···O1iv | 0.88 | 2.43 | 3.116 (2) | 136 |
O3—H3C···N5 | 0.84 | 1.79 | 2.536 (2) | 147 |
O1—H1···N1 | 0.84 | 1.82 | 2.556 (2) | 146 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, y, −z+3/2; (iii) −x+1, −y+2, −z+2; (iv) −x+1, y, −z+5/2. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C13H11N4O2)2] |
Mr | 575.89 |
Crystal system, space group | Monoclinic, P2/c |
Temperature (K) | 173 |
a, b, c (Å) | 10.7704 (9), 13.1196 (11), 19.6427 (14) |
β (°) | 115.630 (4) |
V (Å3) | 2502.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.03 |
Crystal size (mm) | 0.45 × 0.42 × 0.35 |
Data collection | |
Diffractometer | Bruker APEX CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.636, 0.700 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13224, 4662, 4269 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.098, 1.06 |
No. of reflections | 4662 |
No. of parameters | 354 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.85, −0.47 |
Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2003), SHELXTL (Bruker, 2000).
Zn1—N2 | 2.0234 (16) | Zn1—N4 | 2.2980 (17) |
Zn1—O2 | 2.1611 (14) | ||
N2—Zn1—O2 | 75.46 (6) | N2—Zn1—N4 | 73.79 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7B···O2i | 0.88 | 2.17 | 2.882 (2) | 138.0 |
N7—H7A···O3ii | 0.88 | 2.49 | 3.100 (2) | 126.9 |
N3—H3B···O4iii | 0.88 | 2.18 | 2.837 (2) | 131.4 |
N3—H3A···O1iv | 0.88 | 2.43 | 3.116 (2) | 135.5 |
O3—H3C···N5 | 0.84 | 1.79 | 2.536 (2) | 146.5 |
O1—H1···N1 | 0.84 | 1.82 | 2.556 (2) | 146.1 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, y, −z+3/2; (iii) −x+1, −y+2, −z+2; (iv) −x+1, y, −z+5/2. |
The N3-salicyloylpyridine-2-carboxamidrazonato ligand (abbreviated as Hspa) has several potential donor atoms and can occur in different chemical and structural conformations. In the Copper(II) coordination compound containing the dehydrogenated spa ligand (Van Koningsbruggen et al., 1993, 1995), this spa ligand is fairly planar, whereas in the title complex it is slighted bent around the central Zn—N bonds, with a dihedral angle of 21.15 (6)° between the two aromatic rings (Fig. 1).
There are two intramolecular O—H···N hydrogen bonds involving the hydroxyl groups, whereas intermolecular N—H···O hydrogen bonds connect the molecules to build up a chain parallel to the b axis (Fig. 2).