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The title compound, [Zn(C
13H
19N
3O
3)
2(CH
4O)
2](NO
3)
2, is isostructural with the nickel complex reported previously [Chen (2006).
Acta Cryst. E
62, m204–m206]. The Zn atom lies on an inversion centre and is coordinated octahedrally by N and O atoms of two Schiff base ligands and two MeOH molecules in a
trans orientation. In the crystal structure, molecules are linked through O—H
N, O—H
O, N—H
N and N—H
O intermolecular hydrogen bonds, forming chains running along the
b axis.
Supporting information
CCDC reference: 608503
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- Disorder in solvent or counterion
- R factor = 0.057
- wR factor = 0.171
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.49
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.91 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.52 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N4
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.37
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc.
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C10 - C11 ... 1.42 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O7 .. C8 .. 3.00 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact C11 .. O6' .. 3.00 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
2 ALERT type 3 Indicator that the structure quality may be low
2 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.
Bis{2-[2-(diethylamino)ethyliminomethyl]-4-nitrophenolato}dimethanolzinc(II)
dinitrate
top
Crystal data top
[Zn(C13H19N3O3)2(CH4O)2](NO3)2 | Z = 1 |
Mr = 784.10 | F(000) = 412 |
Triclinic, P1 | Dx = 1.434 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.305 (1) Å | Cell parameters from 3889 reflections |
b = 11.083 (2) Å | θ = 2.6–27.5° |
c = 11.126 (2) Å | µ = 0.75 mm−1 |
α = 69.584 (1)° | T = 298 K |
β = 71.080 (1)° | Block, colourless |
γ = 84.204 (1)° | 0.30 × 0.25 × 0.22 mm |
V = 907.8 (3) Å3 | |
Data collection top
Buker SMART APEX 1000 CCD area-detector diffractometer | 3881 independent reflections |
Radiation source: fine-focus sealed tube | 3423 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω scans | θmax = 27.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.806, Tmax = 0.852 | k = −14→14 |
7642 measured reflections | l = −14→14 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.171 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.12P)2 + 0.2978P] where P = (Fo2 + 2Fc2)/3 |
3881 reflections | (Δ/σ)max < 0.001 |
260 parameters | Δρmax = 1.42 e Å−3 |
27 restraints | Δρmin = −0.41 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 | Occ. (<1) |
Zn1 | 1.0000 | 1.0000 | 0.0000 | 0.0463 (2) | |
O1 | 1.1678 (3) | 1.1488 (2) | −0.0825 (2) | 0.0584 (6) | |
O2 | 1.1237 (5) | 1.5743 (3) | 0.1740 (4) | 0.0847 (9) | |
O3 | 1.3177 (5) | 1.6536 (3) | −0.0158 (4) | 0.0887 (10) | |
O4 | 1.1830 (4) | 0.8692 (3) | 0.0887 (4) | 0.0795 (9) | |
O5 | 0.1779 (3) | 0.7839 (4) | 0.5101 (4) | 0.0954 (11) | |
O6 | 0.3438 (8) | 0.6767 (6) | 0.6128 (6) | 0.092 (2) | 0.605 (12) |
O7 | 0.4383 (7) | 0.8359 (7) | 0.4416 (8) | 0.100 (4) | 0.605 (12) |
O6' | 0.4011 (12) | 0.805 (2) | 0.5583 (19) | 0.152 (10) | 0.395 (12) |
O7' | 0.4269 (12) | 0.7486 (17) | 0.4012 (9) | 0.115 (5) | 0.395 (12) |
N1 | 0.9043 (3) | 1.0545 (2) | 0.1734 (2) | 0.0411 (5) | |
N2 | 0.7468 (3) | 0.7833 (3) | 0.4994 (3) | 0.0538 (7) | |
N3 | 1.2155 (5) | 1.5672 (3) | 0.0668 (4) | 0.0644 (9) | |
N4 | 0.3233 (3) | 0.7645 (3) | 0.5090 (4) | 0.0655 (8) | |
C1 | 1.0676 (4) | 1.2558 (3) | 0.0801 (3) | 0.0406 (6) | |
C2 | 1.1767 (4) | 1.2436 (3) | −0.0437 (3) | 0.0450 (6) | |
C3 | 1.3010 (5) | 1.3415 (3) | −0.1268 (4) | 0.0563 (8) | |
H3 | 1.3763 | 1.3342 | −0.2065 | 0.068* | |
C4 | 1.3130 (5) | 1.4470 (3) | −0.0926 (4) | 0.0577 (8) | |
H4 | 1.3931 | 1.5117 | −0.1499 | 0.069* | |
C5 | 1.2043 (4) | 1.4563 (3) | 0.0284 (4) | 0.0500 (7) | |
C6 | 1.0838 (4) | 1.3639 (3) | 0.1135 (3) | 0.0453 (6) | |
H6 | 1.0122 | 1.3726 | 0.1938 | 0.054* | |
C7 | 0.9402 (4) | 1.1616 (3) | 0.1798 (3) | 0.0418 (6) | |
H7 | 0.8776 | 1.1808 | 0.2568 | 0.050* | |
C8 | 0.7748 (4) | 0.9739 (3) | 0.2917 (3) | 0.0436 (6) | |
H8A | 0.6907 | 0.9452 | 0.2637 | 0.052* | |
H8B | 0.7173 | 1.0230 | 0.3501 | 0.052* | |
C9 | 0.8606 (4) | 0.8586 (4) | 0.3669 (3) | 0.0588 (9) | |
H9A | 0.9020 | 0.8033 | 0.3126 | 0.071* | |
H9B | 0.9582 | 0.8883 | 0.3793 | 0.071* | |
C10 | 0.7470 (7) | 0.8561 (5) | 0.6024 (5) | 0.0878 (14) | |
H10A | 0.8550 | 0.8414 | 0.6209 | 0.105* | |
H10B | 0.7379 | 0.9480 | 0.5589 | 0.105* | |
C11 | 0.6130 (8) | 0.8158 (7) | 0.7270 (5) | 0.107 (2) | |
H11A | 0.5057 | 0.8245 | 0.7097 | 0.161* | |
H11B | 0.6143 | 0.8683 | 0.7794 | 0.161* | |
H11C | 0.6287 | 0.7274 | 0.7760 | 0.161* | |
C12 | 0.7953 (6) | 0.6502 (4) | 0.5541 (6) | 0.0870 (14) | |
H12A | 0.7355 | 0.6174 | 0.6501 | 0.104* | |
H12B | 0.9164 | 0.6476 | 0.5426 | 0.104* | |
C13 | 0.7576 (9) | 0.5666 (6) | 0.4901 (8) | 0.117 (2) | |
H13A | 0.6377 | 0.5673 | 0.5027 | 0.176* | |
H13B | 0.7916 | 0.4803 | 0.5302 | 0.176* | |
H13C | 0.8188 | 0.5970 | 0.3954 | 0.176* | |
C14 | 1.3125 (7) | 0.8921 (6) | 0.1286 (8) | 0.1085 (19) | |
H14A | 1.4195 | 0.8877 | 0.0628 | 0.163* | |
H14B | 1.3088 | 0.8285 | 0.2141 | 0.163* | |
H14C | 1.3003 | 0.9761 | 0.1369 | 0.163* | |
H2 | 0.644 (3) | 0.783 (5) | 0.490 (5) | 0.080* | |
H4A | 1.188 (6) | 0.795 (2) | 0.083 (5) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0615 (4) | 0.0353 (3) | 0.0410 (3) | −0.0094 (2) | −0.0072 (2) | −0.0166 (2) |
O1 | 0.0694 (14) | 0.0480 (13) | 0.0536 (13) | −0.0172 (11) | 0.0006 (11) | −0.0254 (10) |
O2 | 0.125 (3) | 0.0560 (17) | 0.092 (2) | 0.0016 (17) | −0.037 (2) | −0.0438 (16) |
O3 | 0.108 (2) | 0.0473 (15) | 0.123 (3) | −0.0182 (16) | −0.044 (2) | −0.0301 (16) |
O4 | 0.105 (2) | 0.0561 (16) | 0.111 (2) | 0.0283 (16) | −0.065 (2) | −0.0476 (16) |
O5 | 0.0423 (14) | 0.155 (3) | 0.100 (2) | −0.0026 (16) | −0.0260 (14) | −0.051 (2) |
O6 | 0.092 (4) | 0.088 (5) | 0.080 (4) | −0.003 (3) | −0.029 (3) | −0.007 (3) |
O7 | 0.063 (3) | 0.098 (5) | 0.103 (6) | −0.028 (3) | −0.029 (3) | 0.020 (4) |
O6' | 0.064 (6) | 0.26 (2) | 0.24 (2) | 0.050 (9) | −0.063 (9) | −0.21 (2) |
O7' | 0.077 (6) | 0.183 (14) | 0.084 (6) | 0.016 (7) | −0.014 (5) | −0.059 (7) |
N1 | 0.0494 (13) | 0.0344 (11) | 0.0371 (11) | −0.0015 (9) | −0.0105 (10) | −0.0113 (9) |
N2 | 0.0411 (13) | 0.0512 (15) | 0.0534 (15) | −0.0053 (11) | −0.0146 (11) | 0.0027 (12) |
N3 | 0.081 (2) | 0.0333 (14) | 0.100 (3) | 0.0045 (13) | −0.057 (2) | −0.0212 (15) |
N4 | 0.0456 (15) | 0.071 (2) | 0.092 (2) | 0.0034 (14) | −0.0249 (16) | −0.0391 (19) |
C1 | 0.0500 (15) | 0.0331 (13) | 0.0436 (14) | 0.0022 (11) | −0.0215 (12) | −0.0126 (11) |
C2 | 0.0517 (16) | 0.0363 (14) | 0.0484 (15) | −0.0042 (12) | −0.0173 (13) | −0.0129 (12) |
C3 | 0.0591 (19) | 0.0496 (18) | 0.0556 (18) | −0.0118 (14) | −0.0099 (15) | −0.0159 (14) |
C4 | 0.063 (2) | 0.0409 (16) | 0.070 (2) | −0.0126 (14) | −0.0273 (17) | −0.0093 (14) |
C5 | 0.0641 (18) | 0.0309 (14) | 0.069 (2) | 0.0039 (12) | −0.0403 (16) | −0.0164 (13) |
C6 | 0.0584 (17) | 0.0352 (14) | 0.0522 (16) | 0.0066 (12) | −0.0291 (14) | −0.0171 (12) |
C7 | 0.0507 (15) | 0.0385 (14) | 0.0389 (13) | 0.0031 (11) | −0.0145 (11) | −0.0162 (11) |
C8 | 0.0449 (14) | 0.0410 (15) | 0.0408 (14) | 0.0008 (11) | −0.0090 (11) | −0.0128 (11) |
C9 | 0.0454 (16) | 0.061 (2) | 0.0507 (18) | −0.0018 (14) | −0.0087 (13) | −0.0008 (15) |
C10 | 0.096 (3) | 0.089 (3) | 0.073 (3) | −0.010 (3) | −0.031 (3) | −0.014 (2) |
C11 | 0.111 (4) | 0.142 (6) | 0.080 (3) | 0.043 (4) | −0.046 (3) | −0.046 (3) |
C12 | 0.078 (3) | 0.064 (3) | 0.100 (3) | −0.001 (2) | −0.030 (3) | −0.001 (2) |
C13 | 0.134 (5) | 0.096 (4) | 0.167 (6) | 0.038 (4) | −0.083 (5) | −0.074 (4) |
C14 | 0.080 (3) | 0.101 (4) | 0.160 (6) | 0.010 (3) | −0.050 (4) | −0.052 (4) |
Geometric parameters (Å, º) top
Zn1—O1i | 2.021 (2) | C3—C4 | 1.371 (5) |
Zn1—O1 | 2.021 (2) | C3—H3 | 0.9300 |
Zn1—N1i | 2.107 (2) | C4—C5 | 1.389 (5) |
Zn1—N1 | 2.107 (2) | C4—H4 | 0.9300 |
Zn1—O4 | 2.217 (3) | C5—C6 | 1.365 (5) |
Zn1—O4i | 2.217 (3) | C6—H6 | 0.9300 |
O1—C2 | 1.283 (4) | C7—H7 | 0.9300 |
O2—N3 | 1.214 (5) | C8—C9 | 1.516 (4) |
O3—N3 | 1.236 (5) | C8—H8A | 0.9700 |
O4—C14 | 1.364 (6) | C8—H8B | 0.9700 |
O4—H4A | 0.84 (3) | C9—H9A | 0.9700 |
O5—N4 | 1.202 (4) | C9—H9B | 0.9700 |
O6—N4 | 1.272 (5) | C10—C11 | 1.424 (8) |
O7—N4 | 1.172 (5) | C10—H10A | 0.9700 |
O6'—N4 | 1.172 (6) | C10—H10B | 0.9700 |
O7'—N4 | 1.287 (6) | C11—H11A | 0.9600 |
N1—C7 | 1.283 (4) | C11—H11B | 0.9600 |
N1—C8 | 1.464 (4) | C11—H11C | 0.9600 |
N2—C12 | 1.457 (5) | C12—C13 | 1.458 (8) |
N2—C9 | 1.470 (4) | C12—H12A | 0.9700 |
N2—C10 | 1.616 (6) | C12—H12B | 0.9700 |
N2—H2 | 0.89 (3) | C13—H13A | 0.9600 |
N3—C5 | 1.455 (4) | C13—H13B | 0.9600 |
C1—C6 | 1.403 (4) | C13—H13C | 0.9600 |
C1—C2 | 1.426 (4) | C14—H14A | 0.9600 |
C1—C7 | 1.447 (4) | C14—H14B | 0.9600 |
C2—C3 | 1.416 (4) | C14—H14C | 0.9600 |
| | | |
O1i—Zn1—O1 | 180.0 | C5—C4—H4 | 120.3 |
O1i—Zn1—N1i | 88.73 (10) | C6—C5—C4 | 121.6 (3) |
O1—Zn1—N1i | 91.27 (10) | C6—C5—N3 | 118.2 (3) |
O1i—Zn1—N1 | 91.27 (10) | C4—C5—N3 | 120.2 (3) |
O1—Zn1—N1 | 88.73 (10) | C5—C6—C1 | 120.1 (3) |
N1i—Zn1—N1 | 180.0 | C5—C6—H6 | 119.9 |
O1i—Zn1—O4 | 88.66 (13) | C1—C6—H6 | 119.9 |
O1—Zn1—O4 | 91.34 (13) | N1—C7—C1 | 127.0 (3) |
N1i—Zn1—O4 | 89.47 (11) | N1—C7—H7 | 116.5 |
N1—Zn1—O4 | 90.53 (11) | C1—C7—H7 | 116.5 |
O1i—Zn1—O4i | 91.34 (13) | N1—C8—C9 | 108.8 (2) |
O1—Zn1—O4i | 88.66 (13) | N1—C8—H8A | 109.9 |
N1i—Zn1—O4i | 90.53 (11) | C9—C8—H8A | 109.9 |
N1—Zn1—O4i | 89.47 (11) | N1—C8—H8B | 109.9 |
O4—Zn1—O4i | 180.0 | C9—C8—H8B | 109.9 |
C2—O1—Zn1 | 130.5 (2) | H8A—C8—H8B | 108.3 |
C14—O4—Zn1 | 131.7 (3) | N2—C9—C8 | 113.1 (3) |
C14—O4—H4A | 112 (3) | N2—C9—H9A | 109.0 |
Zn1—O4—H4A | 115 (3) | C8—C9—H9A | 109.0 |
C7—N1—C8 | 115.8 (2) | N2—C9—H9B | 109.0 |
C7—N1—Zn1 | 124.3 (2) | C8—C9—H9B | 109.0 |
C8—N1—Zn1 | 119.63 (19) | H9A—C9—H9B | 107.8 |
C12—N2—C9 | 115.6 (3) | C11—C10—N2 | 114.0 (5) |
C12—N2—C10 | 108.0 (4) | C11—C10—H10A | 108.8 |
C9—N2—C10 | 106.3 (3) | N2—C10—H10A | 108.8 |
C12—N2—H2 | 108 (3) | C11—C10—H10B | 108.8 |
C9—N2—H2 | 107 (3) | N2—C10—H10B | 108.8 |
C10—N2—H2 | 112 (3) | H10A—C10—H10B | 107.7 |
O2—N3—O3 | 122.5 (3) | C10—C11—H11A | 109.5 |
O2—N3—C5 | 120.5 (3) | C10—C11—H11B | 109.5 |
O3—N3—C5 | 117.0 (4) | H11A—C11—H11B | 109.5 |
O6'—N4—O7 | 59.4 (9) | C10—C11—H11C | 109.5 |
O6'—N4—O5 | 129.0 (6) | H11A—C11—H11C | 109.5 |
O7—N4—O5 | 125.7 (5) | H11B—C11—H11C | 109.5 |
O6'—N4—O6 | 69.7 (11) | N2—C12—C13 | 113.0 (5) |
O7—N4—O6 | 116.5 (4) | N2—C12—H12A | 109.0 |
O5—N4—O6 | 115.0 (4) | C13—C12—H12A | 109.0 |
O6'—N4—O7' | 108.2 (8) | N2—C12—H12B | 109.0 |
O7—N4—O7' | 59.4 (7) | C13—C12—H12B | 109.0 |
O5—N4—O7' | 115.6 (6) | H12A—C12—H12B | 107.8 |
O6—N4—O7' | 110.1 (7) | C12—C13—H13A | 109.5 |
C6—C1—C2 | 119.6 (3) | C12—C13—H13B | 109.5 |
C6—C1—C7 | 115.5 (3) | H13A—C13—H13B | 109.5 |
C2—C1—C7 | 124.9 (3) | C12—C13—H13C | 109.5 |
O1—C2—C3 | 119.0 (3) | H13A—C13—H13C | 109.5 |
O1—C2—C1 | 123.4 (3) | H13B—C13—H13C | 109.5 |
C3—C2—C1 | 117.6 (3) | O4—C14—H14A | 109.5 |
C4—C3—C2 | 121.6 (3) | O4—C14—H14B | 109.5 |
C4—C3—H3 | 119.2 | H14A—C14—H14B | 109.5 |
C2—C3—H3 | 119.2 | O4—C14—H14C | 109.5 |
C3—C4—C5 | 119.3 (3) | H14A—C14—H14C | 109.5 |
C3—C4—H4 | 120.3 | H14B—C14—H14C | 109.5 |
Symmetry code: (i) −x+2, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···N3ii | 0.84 (3) | 2.58 (3) | 3.417 (4) | 177 (4) |
O4—H4A···O2ii | 0.84 (3) | 2.34 (2) | 3.112 (4) | 153 (4) |
O4—H4A···O3ii | 0.84 (3) | 2.22 (3) | 2.978 (4) | 150 (4) |
N2—H2···N4 | 0.89 (3) | 2.63 (3) | 3.509 (4) | 170 (4) |
N2—H2···O6 | 0.89 (3) | 2.59 (3) | 3.348 (7) | 142 (4) |
N2—H2···O7′ | 0.89 (3) | 2.43 (2) | 3.284 (12) | 159 (4) |
N2—H2···O6′ | 0.89 (3) | 1.93 (3) | 2.736 (9) | 148 (4) |
N2—H2···O7 | 0.89 (3) | 1.93 (2) | 2.798 (6) | 163 (5) |
Symmetry code: (ii) x, y−1, z. |
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