The title compound, [Zn(C
13H
10N
3O
3)(NCS)(CH
4O)], is a mononuclear zinc(II) complex. The Zn
II atom has a square-pyramidal coordination geometry. In the basal plane, the Zn
II atom is coordinated by one O atom and two N atoms of the Schiff base ligand, and by the N atom of a thiocyanate anion. The apical position is occupied by the O atom of a coordinated methanol molecule. In the crystal structure, the molecules are linked
via intermolecular O—H
O hydrogen bonds, forming chains parallel to the
a axis.
Supporting information
CCDC reference: 282294
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.108
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C14 .. 5.80 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
3 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
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Methanol[4-nitro-2-(pyridin-2-ylmethyliminomethyl)phenolato](thiocyanato)
zinc(II)
top
Crystal data top
[Zn(C13H10N3O3)(NCS)(CH4O)] | F(000) = 840 |
Mr = 411.73 | Dx = 1.655 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5978 reflections |
a = 10.617 (1) Å | θ = 2.3–28.3° |
b = 11.399 (1) Å | µ = 1.64 mm−1 |
c = 13.691 (1) Å | T = 298 K |
β = 94.133 (1)° | Block, colourless |
V = 1652.6 (2) Å3 | 0.35 × 0.22 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3759 independent reflections |
Radiation source: fine-focus sealed tube | 3188 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.597, Tmax = 0.735 | k = −14→14 |
13802 measured reflections | l = −17→17 |
Refinement top
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0623P)2 + 0.7163P] where P = (Fo2 + 2Fc2)/3 |
3759 reflections | (Δ/σ)max = 0.001 |
230 parameters | Δρmax = 0.46 e Å−3 |
1 restraint | Δρmin = −0.42 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.57714 (3) | 0.98764 (3) | 0.38781 (2) | 0.04361 (12) | |
S1 | 0.76277 (7) | 1.34304 (6) | 0.48582 (7) | 0.0624 (2) | |
O1 | −0.13006 (18) | 1.0790 (2) | 0.22679 (18) | 0.0678 (6) | |
O2 | −0.0803 (2) | 0.9054 (2) | 0.1825 (2) | 0.0808 (7) | |
O3 | 0.42824 (15) | 1.08280 (16) | 0.38876 (15) | 0.0539 (5) | |
O4 | 0.61029 (19) | 1.00709 (18) | 0.21550 (15) | 0.0541 (5) | |
N1 | −0.0536 (2) | 0.9981 (2) | 0.22192 (18) | 0.0524 (6) | |
N2 | 0.47701 (17) | 0.84697 (17) | 0.36168 (15) | 0.0403 (4) | |
N3 | 0.71845 (18) | 0.87134 (18) | 0.40644 (14) | 0.0410 (4) | |
N4 | 0.6809 (2) | 1.1244 (2) | 0.42005 (18) | 0.0542 (6) | |
C1 | 0.2802 (2) | 0.9431 (2) | 0.31451 (16) | 0.0379 (5) | |
C2 | 0.3168 (2) | 1.0579 (2) | 0.34964 (17) | 0.0406 (5) | |
C3 | 0.2247 (2) | 1.1466 (2) | 0.34293 (19) | 0.0464 (6) | |
H3 | 0.2461 | 1.2209 | 0.3668 | 0.056* | |
C4 | 0.1052 (2) | 1.1279 (2) | 0.30271 (18) | 0.0454 (5) | |
H4 | 0.0460 | 1.1881 | 0.2998 | 0.054* | |
C5 | 0.0732 (2) | 1.0171 (2) | 0.26602 (18) | 0.0417 (5) | |
C6 | 0.1576 (2) | 0.9260 (2) | 0.27197 (18) | 0.0434 (5) | |
H6 | 0.1335 | 0.8526 | 0.2476 | 0.052* | |
C7 | 0.3620 (2) | 0.8430 (2) | 0.32659 (18) | 0.0425 (5) | |
H7 | 0.3292 | 0.7702 | 0.3076 | 0.051* | |
C8 | 0.5445 (3) | 0.7359 (2) | 0.3776 (2) | 0.0574 (7) | |
H8A | 0.5339 | 0.6881 | 0.3190 | 0.069* | |
H8B | 0.5099 | 0.6933 | 0.4308 | 0.069* | |
C9 | 0.6828 (2) | 0.7590 (2) | 0.40205 (17) | 0.0430 (5) | |
C10 | 0.7673 (3) | 0.6681 (3) | 0.4200 (2) | 0.0534 (6) | |
H10 | 0.7400 | 0.5906 | 0.4180 | 0.064* | |
C11 | 0.8930 (3) | 0.6945 (3) | 0.4411 (2) | 0.0563 (7) | |
H11 | 0.9518 | 0.6349 | 0.4536 | 0.068* | |
C12 | 0.9308 (3) | 0.8110 (3) | 0.4435 (2) | 0.0573 (7) | |
H12 | 1.0154 | 0.8307 | 0.4565 | 0.069* | |
C13 | 0.8415 (2) | 0.8965 (3) | 0.42634 (18) | 0.0487 (6) | |
H13 | 0.8667 | 0.9746 | 0.4285 | 0.058* | |
C14 | 0.7144 (2) | 1.2161 (2) | 0.44583 (18) | 0.0411 (5) | |
C15 | 0.5646 (3) | 0.9324 (3) | 0.1394 (2) | 0.0668 (8) | |
H15A | 0.5838 | 0.8525 | 0.1569 | 0.100* | |
H15B | 0.6039 | 0.9521 | 0.0805 | 0.100* | |
H15C | 0.4748 | 0.9416 | 0.1286 | 0.100* | |
H4A | 0.6846 (16) | 1.024 (3) | 0.204 (3) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.03411 (17) | 0.04035 (18) | 0.0556 (2) | −0.00178 (10) | −0.00180 (12) | −0.00703 (12) |
S1 | 0.0574 (4) | 0.0384 (4) | 0.0894 (6) | −0.0041 (3) | −0.0096 (4) | −0.0074 (3) |
O1 | 0.0390 (10) | 0.0736 (14) | 0.0882 (15) | 0.0001 (10) | −0.0130 (10) | 0.0126 (12) |
O2 | 0.0554 (13) | 0.0723 (15) | 0.1095 (19) | −0.0151 (11) | −0.0294 (12) | −0.0109 (14) |
O3 | 0.0328 (8) | 0.0446 (10) | 0.0830 (13) | 0.0010 (7) | −0.0059 (8) | −0.0233 (9) |
O4 | 0.0411 (10) | 0.0686 (13) | 0.0517 (11) | −0.0047 (8) | −0.0033 (8) | 0.0047 (8) |
N1 | 0.0376 (12) | 0.0637 (15) | 0.0547 (13) | −0.0093 (10) | −0.0055 (10) | 0.0150 (11) |
N2 | 0.0340 (9) | 0.0355 (10) | 0.0512 (11) | −0.0022 (8) | 0.0022 (8) | 0.0004 (8) |
N3 | 0.0364 (10) | 0.0461 (11) | 0.0402 (10) | 0.0020 (8) | 0.0012 (8) | 0.0026 (8) |
N4 | 0.0414 (11) | 0.0480 (13) | 0.0720 (15) | −0.0066 (9) | −0.0035 (10) | −0.0133 (11) |
C1 | 0.0339 (11) | 0.0393 (12) | 0.0401 (11) | −0.0051 (9) | 0.0011 (9) | −0.0014 (9) |
C2 | 0.0352 (11) | 0.0434 (12) | 0.0430 (12) | −0.0036 (9) | 0.0023 (9) | −0.0067 (10) |
C3 | 0.0417 (12) | 0.0436 (13) | 0.0532 (14) | 0.0006 (10) | −0.0014 (10) | −0.0101 (11) |
C4 | 0.0364 (12) | 0.0500 (14) | 0.0494 (13) | 0.0043 (10) | 0.0010 (10) | 0.0033 (11) |
C5 | 0.0304 (11) | 0.0546 (14) | 0.0396 (12) | −0.0071 (9) | −0.0017 (9) | 0.0070 (10) |
C6 | 0.0408 (12) | 0.0435 (13) | 0.0456 (13) | −0.0110 (10) | −0.0002 (10) | 0.0009 (10) |
C7 | 0.0424 (12) | 0.0370 (12) | 0.0482 (13) | −0.0084 (9) | 0.0045 (10) | −0.0014 (10) |
C8 | 0.0457 (14) | 0.0399 (14) | 0.086 (2) | −0.0002 (11) | −0.0013 (13) | 0.0054 (13) |
C9 | 0.0431 (13) | 0.0446 (13) | 0.0416 (12) | 0.0051 (10) | 0.0053 (10) | 0.0014 (10) |
C10 | 0.0577 (16) | 0.0484 (15) | 0.0546 (15) | 0.0128 (12) | 0.0073 (12) | 0.0007 (12) |
C11 | 0.0487 (14) | 0.0681 (18) | 0.0524 (15) | 0.0220 (13) | 0.0056 (11) | 0.0022 (13) |
C12 | 0.0384 (13) | 0.078 (2) | 0.0548 (15) | 0.0104 (13) | −0.0014 (11) | 0.0023 (14) |
C13 | 0.0380 (12) | 0.0579 (15) | 0.0495 (13) | 0.0003 (11) | −0.0022 (10) | 0.0050 (12) |
C14 | 0.0272 (10) | 0.0457 (13) | 0.0496 (13) | 0.0015 (9) | −0.0034 (9) | 0.0000 (10) |
C15 | 0.073 (2) | 0.0646 (19) | 0.0629 (18) | −0.0016 (16) | 0.0036 (15) | −0.0048 (15) |
Geometric parameters (Å, º) top
Zn1—O3 | 1.918 (2) | C3—C4 | 1.363 (3) |
Zn1—N4 | 1.941 (2) | C3—H3 | 0.93 |
Zn1—N2 | 1.943 (2) | C4—C5 | 1.392 (4) |
Zn1—N3 | 2.005 (2) | C4—H4 | 0.93 |
Zn1—O4 | 2.420 (2) | C5—C6 | 1.370 (4) |
S1—C14 | 1.618 (3) | C6—H6 | 0.93 |
O1—N1 | 1.234 (3) | C7—H7 | 0.93 |
O2—N1 | 1.211 (3) | C8—C9 | 1.505 (3) |
O3—C2 | 1.294 (3) | C8—H8A | 0.97 |
O4—C15 | 1.405 (4) | C8—H8B | 0.97 |
O4—H4A | 0.835 (10) | C9—C10 | 1.381 (3) |
N1—C5 | 1.451 (3) | C10—C11 | 1.378 (4) |
N2—C7 | 1.280 (3) | C10—H10 | 0.93 |
N2—C8 | 1.464 (3) | C11—C12 | 1.387 (5) |
N3—C9 | 1.336 (3) | C11—H11 | 0.93 |
N3—C13 | 1.346 (3) | C12—C13 | 1.368 (4) |
N4—C14 | 1.151 (3) | C12—H12 | 0.93 |
C1—C6 | 1.400 (3) | C13—H13 | 0.93 |
C1—C7 | 1.437 (3) | C15—H15A | 0.96 |
C1—C2 | 1.439 (3) | C15—H15B | 0.96 |
C2—C3 | 1.405 (3) | C15—H15C | 0.96 |
| | | |
O3—Zn1—N4 | 89.93 (8) | C6—C5—N1 | 119.7 (2) |
O3—Zn1—N2 | 91.59 (7) | C4—C5—N1 | 118.7 (2) |
N4—Zn1—N2 | 177.05 (9) | C5—C6—C1 | 120.3 (2) |
O3—Zn1—N3 | 169.37 (9) | C5—C6—H6 | 119.9 |
N4—Zn1—N3 | 95.45 (9) | C1—C6—H6 | 119.9 |
N2—Zn1—N3 | 82.65 (8) | N2—C7—C1 | 124.6 (2) |
O3—Zn1—O4 | 97.62 (8) | N2—C7—H7 | 117.7 |
N4—Zn1—O4 | 91.61 (9) | C1—C7—H7 | 117.7 |
N2—Zn1—O4 | 90.70 (8) | N2—C8—C9 | 110.0 (2) |
N3—Zn1—O4 | 91.40 (7) | N2—C8—H8A | 109.7 |
C2—O3—Zn1 | 127.05 (16) | C9—C8—H8A | 109.7 |
C15—O4—Zn1 | 126.94 (19) | N2—C8—H8B | 109.7 |
C15—O4—H4A | 107 (3) | C9—C8—H8B | 109.7 |
Zn1—O4—H4A | 114 (3) | H8A—C8—H8B | 108.2 |
O2—N1—O1 | 122.8 (2) | N3—C9—C10 | 122.2 (2) |
O2—N1—C5 | 119.8 (2) | N3—C9—C8 | 116.5 (2) |
O1—N1—C5 | 117.4 (2) | C10—C9—C8 | 121.3 (2) |
C7—N2—C8 | 118.0 (2) | C11—C10—C9 | 118.7 (3) |
C7—N2—Zn1 | 126.34 (17) | C11—C10—H10 | 120.6 |
C8—N2—Zn1 | 115.53 (15) | C9—C10—H10 | 120.6 |
C9—N3—C13 | 118.7 (2) | C10—C11—C12 | 119.2 (3) |
C9—N3—Zn1 | 114.92 (16) | C10—C11—H11 | 120.4 |
C13—N3—Zn1 | 126.28 (19) | C12—C11—H11 | 120.4 |
C14—N4—Zn1 | 163.1 (2) | C13—C12—C11 | 118.8 (3) |
C6—C1—C7 | 118.3 (2) | C13—C12—H12 | 120.6 |
C6—C1—C2 | 119.1 (2) | C11—C12—H12 | 120.6 |
C7—C1—C2 | 122.5 (2) | N3—C13—C12 | 122.3 (3) |
O3—C2—C3 | 118.7 (2) | N3—C13—H13 | 118.9 |
O3—C2—C1 | 123.7 (2) | C12—C13—H13 | 118.9 |
C3—C2—C1 | 117.6 (2) | N4—C14—S1 | 178.0 (2) |
C4—C3—C2 | 122.5 (2) | O4—C15—H15A | 109.5 |
C4—C3—H3 | 118.8 | O4—C15—H15B | 109.5 |
C2—C3—H3 | 118.8 | H15A—C15—H15B | 109.5 |
C3—C4—C5 | 118.9 (2) | O4—C15—H15C | 109.5 |
C3—C4—H4 | 120.5 | H15A—C15—H15C | 109.5 |
C5—C4—H4 | 120.5 | H15B—C15—H15C | 109.5 |
C6—C5—C4 | 121.6 (2) | | |
| | | |
N4—Zn1—O3—C2 | 161.6 (2) | C1—C2—C3—C4 | −1.6 (4) |
N2—Zn1—O3—C2 | −20.9 (2) | C2—C3—C4—C5 | −0.6 (4) |
N3—Zn1—O3—C2 | −77.8 (5) | C3—C4—C5—C6 | 1.9 (4) |
O4—Zn1—O3—C2 | 70.0 (2) | C3—C4—C5—N1 | −179.1 (2) |
O3—Zn1—O4—C15 | −92.0 (2) | O2—N1—C5—C6 | −7.0 (4) |
N4—Zn1—O4—C15 | 177.9 (2) | O1—N1—C5—C6 | 173.0 (2) |
N2—Zn1—O4—C15 | −0.3 (2) | O2—N1—C5—C4 | 174.0 (3) |
N3—Zn1—O4—C15 | 82.4 (2) | O1—N1—C5—C4 | −6.0 (3) |
O3—Zn1—N2—C7 | 19.7 (2) | C4—C5—C6—C1 | −0.9 (4) |
N3—Zn1—N2—C7 | −169.3 (2) | N1—C5—C6—C1 | −179.9 (2) |
O4—Zn1—N2—C7 | −77.9 (2) | C7—C1—C6—C5 | 174.9 (2) |
O3—Zn1—N2—C8 | −165.1 (2) | C2—C1—C6—C5 | −1.5 (3) |
N3—Zn1—N2—C8 | 5.98 (19) | C8—N2—C7—C1 | 174.5 (2) |
O4—Zn1—N2—C8 | 97.30 (19) | Zn1—N2—C7—C1 | −10.3 (4) |
O3—Zn1—N3—C9 | 52.2 (5) | C6—C1—C7—N2 | 177.9 (2) |
N4—Zn1—N3—C9 | 172.28 (17) | C2—C1—C7—N2 | −5.9 (4) |
N2—Zn1—N3—C9 | −5.45 (17) | C7—N2—C8—C9 | 170.2 (2) |
O4—Zn1—N3—C9 | −95.97 (17) | Zn1—N2—C8—C9 | −5.5 (3) |
O3—Zn1—N3—C13 | −125.0 (4) | C13—N3—C9—C10 | 1.9 (4) |
N4—Zn1—N3—C13 | −4.9 (2) | Zn1—N3—C9—C10 | −175.45 (19) |
N2—Zn1—N3—C13 | 177.4 (2) | C13—N3—C9—C8 | −178.8 (2) |
O4—Zn1—N3—C13 | 86.9 (2) | Zn1—N3—C9—C8 | 3.8 (3) |
O3—Zn1—N4—C14 | 17.9 (8) | N2—C8—C9—N3 | 1.0 (3) |
N3—Zn1—N4—C14 | −153.0 (8) | N2—C8—C9—C10 | −179.8 (2) |
O4—Zn1—N4—C14 | 115.5 (8) | N3—C9—C10—C11 | −1.4 (4) |
Zn1—O3—C2—C3 | −169.03 (18) | C8—C9—C10—C11 | 179.3 (3) |
Zn1—O3—C2—C1 | 12.7 (4) | C9—C10—C11—C12 | −0.1 (4) |
C6—C1—C2—O3 | −179.0 (2) | C10—C11—C12—C13 | 1.1 (4) |
C7—C1—C2—O3 | 4.8 (4) | C9—N3—C13—C12 | −0.9 (4) |
C6—C1—C2—C3 | 2.7 (3) | Zn1—N3—C13—C12 | 176.1 (2) |
C7—C1—C2—C3 | −173.5 (2) | C11—C12—C13—N3 | −0.6 (4) |
O3—C2—C3—C4 | 179.9 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O1i | 0.84 (1) | 2.07 (2) | 2.869 (3) | 161 (4) |
Symmetry code: (i) x+1, y, z. |