Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059296/xu2375sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059296/xu2375Isup2.hkl |
CCDC reference: 672728
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.012 Å
- R factor = 0.040
- wR factor = 0.150
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12 PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... H2<I>N< PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... H4<I>N<
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.47 From the CIF: _reflns_number_total 4493 Count of symmetry unique reflns 2781 Completeness (_total/calc) 161.56% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1712 Fraction of Friedel pairs measured 0.616 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 2 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
Zinc sulfate heptahydrate (1.44 g, 5 mmol) was added to an aqueous solution (25 ml) of 4-formylbenzoic acid (1.5 g, 10 mmol) and imidazole (0.68 g, 10 mmol). The pH value of the mixture was about 6. The solution was allowed to evaporate at room temperature; colorless prismatic crystals separated from the filtered solution after several days. CH&N elemental analysis. Calc. for C22H18N4O6Zn: C 52.87, H 3.63, N 11.21%. Found: C 52.88, H 3.68, N 11.18%.
The carbon- and nitrogen bound H atoms were generated geometrically (C–H 0.93, N–H 0.86 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C,N).
The final difference Fourier map had a large peak /deep hole near Zn1.
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2007).
[Zn(C8H5O3)2(C3H4N2)2] | F(000) = 512 |
Mr = 499.77 | Dx = 1.477 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 8013 reflections |
a = 11.9413 (9) Å | θ = 3.1–27.5° |
b = 7.0455 (5) Å | µ = 1.14 mm−1 |
c = 14.2092 (9) Å | T = 295 K |
β = 109.904 (2)° | Prism, colorless |
V = 1124.1 (1) Å3 | 0.36 × 0.25 × 0.21 mm |
Z = 2 |
Rigaku RAXIS-RAPID IP diffractometer | 4493 independent reflections |
Radiation source: fine-focus sealed tube | 2901 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω scan | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −15→15 |
Tmin = 0.662, Tmax = 0.796 | k = −9→8 |
11106 measured reflections | l = −18→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0471P)2 + 1.7346P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max = 0.001 |
4493 reflections | Δρmax = 1.17 e Å−3 |
299 parameters | Δρmin = −1.12 e Å−3 |
1 restraint | Absolute structure: Flack (1983) parameter from 1716 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (2) |
[Zn(C8H5O3)2(C3H4N2)2] | V = 1124.1 (1) Å3 |
Mr = 499.77 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.9413 (9) Å | µ = 1.14 mm−1 |
b = 7.0455 (5) Å | T = 295 K |
c = 14.2092 (9) Å | 0.36 × 0.25 × 0.21 mm |
β = 109.904 (2)° |
Rigaku RAXIS-RAPID IP diffractometer | 4493 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2901 reflections with I > 2σ(I) |
Tmin = 0.662, Tmax = 0.796 | Rint = 0.042 |
11106 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.150 | Δρmax = 1.17 e Å−3 |
S = 1.13 | Δρmin = −1.12 e Å−3 |
4493 reflections | Absolute structure: Flack (1983) parameter from 1716 Friedel pairs |
299 parameters | Absolute structure parameter: 0.01 (2) |
1 restraint |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.77235 (5) | 0.49998 (13) | 0.20968 (4) | 0.0464 (2) | |
O1 | 0.8971 (4) | 0.3416 (7) | 0.1932 (4) | 0.0585 (13) | |
O2 | 0.7697 (4) | 0.1549 (8) | 0.0823 (4) | 0.0684 (15) | |
O3 | 1.3608 (7) | −0.2711 (12) | 0.1953 (5) | 0.111 (3) | |
O4 | 0.6612 (4) | 0.3861 (8) | 0.2687 (3) | 0.0608 (13) | |
O5 | 0.7938 (4) | 0.3692 (9) | 0.4217 (4) | 0.0719 (15) | |
O6 | 0.1902 (7) | 0.3427 (14) | 0.4523 (6) | 0.126 (3) | |
N1 | 0.6505 (4) | 0.5887 (8) | 0.0812 (4) | 0.0461 (12) | |
N2 | 0.4747 (5) | 0.6479 (9) | −0.0238 (5) | 0.0631 (17) | |
H2n | 0.3998 | 0.6732 | −0.0469 | 0.076* | |
N3 | 0.8663 (4) | 0.7125 (8) | 0.2943 (4) | 0.0473 (13) | |
N4 | 1.0097 (5) | 0.8557 (10) | 0.4062 (4) | 0.0622 (16) | |
H4n | 1.0774 | 0.8759 | 0.4521 | 0.075* | |
C1 | 0.6901 (5) | 0.3684 (10) | 0.3637 (5) | 0.0498 (16) | |
C2 | 0.5873 (6) | 0.3511 (9) | 0.4011 (4) | 0.0462 (15) | |
C3 | 0.6076 (7) | 0.3316 (11) | 0.5034 (5) | 0.0585 (18) | |
H3 | 0.6847 | 0.3235 | 0.5489 | 0.070* | |
C4 | 0.5090 (8) | 0.3245 (11) | 0.5363 (5) | 0.064 (2) | |
H4 | 0.5215 | 0.3125 | 0.6043 | 0.077* | |
C5 | 0.3954 (7) | 0.3348 (11) | 0.4702 (6) | 0.0616 (19) | |
C6 | 0.3780 (7) | 0.3571 (12) | 0.3701 (6) | 0.064 (2) | |
H6 | 0.3008 | 0.3680 | 0.3249 | 0.077* | |
C7 | 0.4699 (6) | 0.3635 (11) | 0.3360 (5) | 0.0535 (17) | |
H7 | 0.4550 | 0.3765 | 0.2677 | 0.064* | |
C8 | 0.2937 (10) | 0.3301 (16) | 0.5073 (8) | 0.091 (3) | |
H8 | 0.3094 | 0.3168 | 0.5757 | 0.109* | |
C9 | 0.8711 (5) | 0.1953 (10) | 0.1381 (5) | 0.0450 (14) | |
C10 | 0.9721 (6) | 0.0645 (9) | 0.1431 (5) | 0.0459 (16) | |
C11 | 0.9491 (7) | −0.1102 (12) | 0.0963 (6) | 0.064 (2) | |
H11 | 0.8710 | −0.1469 | 0.0618 | 0.077* | |
C12 | 1.0425 (8) | −0.2306 (12) | 0.1007 (6) | 0.074 (2) | |
H12 | 1.0270 | −0.3478 | 0.0688 | 0.089* | |
C13 | 1.1581 (7) | −0.1771 (12) | 0.1522 (6) | 0.062 (2) | |
C14 | 1.1811 (6) | −0.0046 (18) | 0.1993 (5) | 0.073 (2) | |
H14 | 1.2593 | 0.0317 | 0.2336 | 0.087* | |
C15 | 1.0887 (5) | 0.1152 (11) | 0.1958 (6) | 0.062 (2) | |
H15 | 1.1047 | 0.2310 | 0.2292 | 0.075* | |
C16 | 1.2565 (9) | −0.3093 (15) | 0.1549 (7) | 0.082 (3) | |
H16 | 1.2368 | −0.4270 | 0.1241 | 0.098* | |
C17 | 0.6563 (6) | 0.5897 (11) | −0.0136 (5) | 0.0551 (17) | |
H17 | 0.7242 | 0.5678 | −0.0300 | 0.066* | |
C18 | 0.5469 (7) | 0.6276 (12) | −0.0788 (5) | 0.064 (2) | |
H18 | 0.5252 | 0.6379 | −0.1480 | 0.077* | |
C19 | 0.5387 (5) | 0.6224 (10) | 0.0710 (5) | 0.0496 (16) | |
H19 | 0.5089 | 0.6274 | 0.1235 | 0.060* | |
C20 | 0.8343 (6) | 0.8961 (11) | 0.3001 (5) | 0.0549 (17) | |
H20 | 0.7622 | 0.9505 | 0.2619 | 0.066* | |
C21 | 0.9231 (6) | 0.9861 (16) | 0.3696 (5) | 0.0631 (17) | |
H21 | 0.9248 | 1.1126 | 0.3887 | 0.076* | |
C22 | 0.9740 (6) | 0.6922 (12) | 0.3605 (5) | 0.0578 (18) | |
H22 | 1.0180 | 0.5803 | 0.3731 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0356 (3) | 0.0558 (4) | 0.0432 (3) | 0.0037 (4) | 0.0074 (2) | −0.0028 (5) |
O1 | 0.041 (2) | 0.057 (3) | 0.070 (3) | 0.004 (2) | 0.009 (2) | −0.011 (3) |
O2 | 0.035 (2) | 0.080 (4) | 0.074 (3) | 0.004 (2) | −0.002 (2) | −0.016 (3) |
O3 | 0.096 (5) | 0.148 (7) | 0.102 (5) | 0.067 (5) | 0.051 (4) | 0.033 (5) |
O4 | 0.054 (3) | 0.076 (4) | 0.044 (2) | −0.005 (2) | 0.006 (2) | 0.003 (2) |
O5 | 0.049 (3) | 0.101 (4) | 0.055 (3) | 0.007 (3) | 0.005 (2) | 0.016 (3) |
O6 | 0.090 (5) | 0.172 (8) | 0.134 (6) | 0.009 (6) | 0.061 (5) | 0.006 (6) |
N1 | 0.032 (2) | 0.061 (3) | 0.043 (3) | 0.005 (2) | 0.010 (2) | −0.004 (2) |
N2 | 0.034 (3) | 0.072 (4) | 0.072 (4) | 0.007 (3) | 0.003 (3) | 0.008 (3) |
N3 | 0.037 (3) | 0.056 (4) | 0.044 (3) | 0.004 (2) | 0.007 (2) | 0.001 (3) |
N4 | 0.058 (4) | 0.071 (4) | 0.048 (3) | −0.015 (3) | 0.006 (3) | −0.015 (3) |
C1 | 0.040 (3) | 0.052 (4) | 0.051 (4) | 0.007 (3) | 0.007 (3) | 0.002 (3) |
C2 | 0.055 (4) | 0.042 (4) | 0.042 (3) | 0.005 (3) | 0.018 (3) | −0.001 (3) |
C3 | 0.062 (4) | 0.061 (5) | 0.053 (4) | 0.010 (3) | 0.019 (3) | 0.003 (4) |
C4 | 0.096 (6) | 0.054 (5) | 0.048 (4) | 0.006 (4) | 0.032 (4) | 0.009 (3) |
C5 | 0.061 (5) | 0.057 (5) | 0.074 (5) | 0.007 (4) | 0.031 (4) | 0.004 (4) |
C6 | 0.050 (4) | 0.075 (5) | 0.070 (5) | −0.006 (4) | 0.025 (4) | −0.004 (4) |
C7 | 0.049 (4) | 0.062 (5) | 0.047 (3) | 0.003 (3) | 0.013 (3) | −0.006 (3) |
C8 | 0.099 (8) | 0.095 (8) | 0.099 (7) | 0.014 (6) | 0.060 (6) | 0.003 (6) |
C9 | 0.040 (3) | 0.048 (4) | 0.046 (3) | 0.005 (3) | 0.012 (3) | 0.001 (3) |
C10 | 0.040 (3) | 0.046 (4) | 0.054 (4) | 0.008 (2) | 0.019 (3) | 0.003 (3) |
C11 | 0.059 (5) | 0.060 (5) | 0.073 (5) | −0.003 (4) | 0.023 (4) | −0.013 (4) |
C12 | 0.096 (7) | 0.055 (5) | 0.077 (5) | 0.016 (4) | 0.037 (5) | −0.010 (4) |
C13 | 0.067 (5) | 0.069 (5) | 0.058 (4) | 0.019 (4) | 0.032 (4) | 0.008 (4) |
C14 | 0.046 (3) | 0.090 (6) | 0.079 (4) | 0.027 (6) | 0.017 (3) | −0.012 (7) |
C15 | 0.033 (3) | 0.067 (5) | 0.083 (5) | 0.003 (3) | 0.013 (3) | −0.021 (4) |
C16 | 0.093 (7) | 0.091 (7) | 0.073 (5) | 0.042 (6) | 0.042 (5) | 0.018 (5) |
C17 | 0.053 (4) | 0.066 (5) | 0.043 (3) | 0.002 (3) | 0.012 (3) | 0.003 (3) |
C18 | 0.058 (4) | 0.076 (6) | 0.046 (4) | 0.001 (4) | 0.003 (3) | 0.008 (4) |
C19 | 0.031 (3) | 0.062 (4) | 0.049 (3) | 0.004 (3) | 0.005 (3) | −0.003 (3) |
C20 | 0.049 (4) | 0.065 (5) | 0.051 (4) | 0.011 (3) | 0.017 (3) | 0.003 (3) |
C21 | 0.077 (4) | 0.054 (4) | 0.061 (4) | −0.004 (5) | 0.027 (3) | −0.010 (5) |
C22 | 0.045 (4) | 0.064 (5) | 0.052 (4) | −0.003 (3) | 0.000 (3) | −0.010 (4) |
Zn1—O1 | 1.938 (5) | C5—C6 | 1.375 (10) |
Zn1—O4 | 1.966 (5) | C5—C8 | 1.480 (12) |
Zn1—N1 | 2.007 (5) | C6—C7 | 1.342 (9) |
Zn1—N3 | 2.007 (6) | C6—H6 | 0.9300 |
O1—C9 | 1.267 (8) | C7—H7 | 0.9300 |
O2—C9 | 1.235 (7) | C8—H8 | 0.9300 |
O3—C16 | 1.212 (11) | C9—C10 | 1.500 (9) |
O4—C1 | 1.281 (7) | C10—C11 | 1.382 (10) |
O5—C1 | 1.232 (7) | C10—C15 | 1.384 (9) |
O6—C8 | 1.220 (11) | C11—C12 | 1.385 (11) |
N1—C19 | 1.315 (7) | C11—H11 | 0.9300 |
N1—C17 | 1.373 (8) | C12—C13 | 1.377 (12) |
N2—C19 | 1.315 (8) | C12—H12 | 0.9300 |
N2—C18 | 1.354 (10) | C13—C14 | 1.369 (14) |
N2—H2n | 0.8600 | C13—C16 | 1.489 (11) |
N3—C22 | 1.318 (8) | C14—C15 | 1.377 (10) |
N3—C20 | 1.360 (9) | C14—H14 | 0.9300 |
N4—C22 | 1.320 (10) | C15—H15 | 0.9300 |
N4—C21 | 1.348 (11) | C16—H16 | 0.9300 |
N4—H4n | 0.8600 | C17—C18 | 1.346 (10) |
C1—C2 | 1.499 (9) | C17—H17 | 0.9300 |
C2—C7 | 1.395 (9) | C18—H18 | 0.9300 |
C2—C3 | 1.397 (9) | C19—H19 | 0.9300 |
C3—C4 | 1.408 (11) | C20—C21 | 1.337 (10) |
C3—H3 | 0.9300 | C20—H20 | 0.9300 |
C4—C5 | 1.364 (11) | C21—H21 | 0.9300 |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
O1—Zn1—O4 | 118.3 (2) | C5—C8—H8 | 118.5 |
O1—Zn1—N1 | 114.7 (2) | O2—C9—O1 | 124.4 (6) |
O1—Zn1—N3 | 101.9 (2) | O2—C9—C10 | 119.1 (6) |
O4—Zn1—N1 | 97.4 (2) | O1—C9—C10 | 116.5 (5) |
O4—Zn1—N3 | 111.7 (2) | C11—C10—C15 | 119.3 (6) |
N1—Zn1—N3 | 113.4 (2) | C11—C10—C9 | 120.0 (7) |
C9—O1—Zn1 | 120.4 (4) | C15—C10—C9 | 120.7 (6) |
C1—O4—Zn1 | 120.7 (4) | C10—C11—C12 | 119.9 (8) |
C19—N1—C17 | 106.2 (5) | C10—C11—H11 | 120.1 |
C19—N1—Zn1 | 123.5 (4) | C12—C11—H11 | 120.1 |
C17—N1—Zn1 | 129.1 (4) | C13—C12—C11 | 120.2 (8) |
C19—N2—C18 | 108.4 (5) | C13—C12—H12 | 119.9 |
C19—N2—H2n | 125.8 | C11—C12—H12 | 119.9 |
C18—N2—H2n | 125.8 | C14—C13—C12 | 120.1 (7) |
C22—N3—C20 | 106.6 (6) | C14—C13—C16 | 121.1 (8) |
C22—N3—Zn1 | 123.9 (5) | C12—C13—C16 | 118.8 (9) |
C20—N3—Zn1 | 129.5 (4) | C13—C14—C15 | 120.1 (7) |
C22—N4—C21 | 109.2 (6) | C13—C14—H14 | 120.0 |
C22—N4—H4n | 125.4 | C15—C14—H14 | 120.0 |
C21—N4—H4n | 125.4 | C14—C15—C10 | 120.5 (8) |
O5—C1—O4 | 123.6 (6) | C14—C15—H15 | 119.8 |
O5—C1—C2 | 121.4 (6) | C10—C15—H15 | 119.8 |
O4—C1—C2 | 115.0 (5) | O3—C16—C13 | 123.3 (10) |
C7—C2—C3 | 118.4 (6) | O3—C16—H16 | 118.4 |
C7—C2—C1 | 121.3 (6) | C13—C16—H16 | 118.4 |
C3—C2—C1 | 120.3 (6) | C18—C17—N1 | 108.4 (7) |
C2—C3—C4 | 118.7 (7) | C18—C17—H17 | 125.8 |
C2—C3—H3 | 120.6 | N1—C17—H17 | 125.8 |
C4—C3—H3 | 120.6 | C17—C18—N2 | 106.4 (6) |
C5—C4—C3 | 121.1 (7) | C17—C18—H18 | 126.8 |
C5—C4—H4 | 119.4 | N2—C18—H18 | 126.8 |
C3—C4—H4 | 119.4 | N1—C19—N2 | 110.6 (6) |
C4—C5—C6 | 118.9 (7) | N1—C19—H19 | 124.7 |
C4—C5—C8 | 119.8 (8) | N2—C19—H19 | 124.7 |
C6—C5—C8 | 121.2 (8) | C21—C20—N3 | 109.1 (7) |
C7—C6—C5 | 121.5 (7) | C21—C20—H20 | 125.4 |
C7—C6—H6 | 119.2 | N3—C20—H20 | 125.4 |
C5—C6—H6 | 119.2 | C20—C21—N4 | 105.9 (8) |
C6—C7—C2 | 121.3 (7) | C20—C21—H21 | 127.1 |
C6—C7—H7 | 119.4 | N4—C21—H21 | 127.1 |
C2—C7—H7 | 119.4 | N3—C22—N4 | 109.2 (7) |
O6—C8—C5 | 123.0 (10) | N3—C22—H22 | 125.4 |
O6—C8—H8 | 118.5 | N4—C22—H22 | 125.4 |
O4—Zn1—O1—C9 | 61.0 (5) | C4—C5—C8—O6 | 178.4 (10) |
N3—Zn1—O1—C9 | −176.1 (5) | C6—C5—C8—O6 | 1.1 (15) |
N1—Zn1—O1—C9 | −53.2 (6) | Zn1—O1—C9—O2 | 9.4 (9) |
O1—Zn1—O4—C1 | 81.4 (6) | Zn1—O1—C9—C10 | −170.2 (4) |
N3—Zn1—O4—C1 | −36.4 (6) | O2—C9—C10—C11 | −8.5 (10) |
N1—Zn1—O4—C1 | −155.2 (5) | O1—C9—C10—C11 | 171.1 (6) |
O1—Zn1—N1—C19 | 149.5 (5) | O2—C9—C10—C15 | 172.6 (7) |
O4—Zn1—N1—C19 | 23.6 (6) | O1—C9—C10—C15 | −7.7 (10) |
N3—Zn1—N1—C19 | −94.0 (5) | C15—C10—C11—C12 | −1.4 (11) |
O1—Zn1—N1—C17 | −16.0 (7) | C9—C10—C11—C12 | 179.8 (7) |
O4—Zn1—N1—C17 | −141.9 (6) | C10—C11—C12—C13 | 0.4 (13) |
N3—Zn1—N1—C17 | 100.5 (6) | C11—C12—C13—C14 | 0.1 (13) |
O1—Zn1—N3—C22 | −31.2 (6) | C11—C12—C13—C16 | −179.6 (8) |
O4—Zn1—N3—C22 | 96.1 (6) | C12—C13—C14—C15 | 0.4 (13) |
N1—Zn1—N3—C22 | −155.0 (5) | C16—C13—C14—C15 | −179.9 (8) |
O1—Zn1—N3—C20 | 152.0 (6) | C13—C14—C15—C10 | −1.4 (13) |
O4—Zn1—N3—C20 | −80.7 (6) | C11—C10—C15—C14 | 1.9 (12) |
N1—Zn1—N3—C20 | 28.2 (6) | C9—C10—C15—C14 | −179.3 (7) |
Zn1—O4—C1—O5 | −20.8 (10) | C14—C13—C16—O3 | −2.4 (14) |
Zn1—O4—C1—C2 | 157.8 (5) | C12—C13—C16—O3 | 177.2 (8) |
O5—C1—C2—C7 | 175.5 (7) | C19—N1—C17—C18 | 1.1 (8) |
O4—C1—C2—C7 | −3.1 (10) | Zn1—N1—C17—C18 | 168.6 (5) |
O5—C1—C2—C3 | −1.3 (11) | N1—C17—C18—N2 | −0.6 (9) |
O4—C1—C2—C3 | −179.8 (6) | C19—N2—C18—C17 | −0.2 (9) |
C7—C2—C3—C4 | 0.3 (11) | C17—N1—C19—N2 | −1.2 (8) |
C1—C2—C3—C4 | 177.1 (7) | Zn1—N1—C19—N2 | −169.6 (5) |
C2—C3—C4—C5 | 0.5 (11) | C18—N2—C19—N1 | 0.9 (9) |
C3—C4—C5—C6 | −1.6 (12) | C22—N3—C20—C21 | 0.3 (8) |
C3—C4—C5—C8 | −179.0 (8) | Zn1—N3—C20—C21 | 177.4 (5) |
C4—C5—C6—C7 | 1.9 (13) | N3—C20—C21—N4 | 0.0 (8) |
C8—C5—C6—C7 | 179.3 (9) | C22—N4—C21—C20 | −0.2 (8) |
C5—C6—C7—C2 | −1.1 (13) | C20—N3—C22—N4 | −0.4 (8) |
C3—C2—C7—C6 | 0.0 (11) | Zn1—N3—C22—N4 | −177.7 (5) |
C1—C2—C7—C6 | −176.8 (7) | C21—N4—C22—N3 | 0.4 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2n···O2i | 0.86 | 1.92 | 2.749 (7) | 163 |
N4—H4n···O5ii | 0.86 | 1.93 | 2.754 (7) | 162 |
Symmetry codes: (i) −x+1, y+1/2, −z; (ii) −x+2, y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C8H5O3)2(C3H4N2)2] |
Mr | 499.77 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 295 |
a, b, c (Å) | 11.9413 (9), 7.0455 (5), 14.2092 (9) |
β (°) | 109.904 (2) |
V (Å3) | 1124.1 (1) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.14 |
Crystal size (mm) | 0.36 × 0.25 × 0.21 |
Data collection | |
Diffractometer | Rigaku RAXIS-RAPID IP diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.662, 0.796 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11106, 4493, 2901 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.150, 1.13 |
No. of reflections | 4493 |
No. of parameters | 299 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.17, −1.12 |
Absolute structure | Flack (1983) parameter from 1716 Friedel pairs |
Absolute structure parameter | 0.01 (2) |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003), publCIF (Westrip, 2007).
Zn1—O1 | 1.938 (5) | Zn1—N1 | 2.007 (5) |
Zn1—O4 | 1.966 (5) | Zn1—N3 | 2.007 (6) |
O1—Zn1—O4 | 118.3 (2) | O4—Zn1—N1 | 97.4 (2) |
O1—Zn1—N1 | 114.7 (2) | O4—Zn1—N3 | 111.7 (2) |
O1—Zn1—N3 | 101.9 (2) | N1—Zn1—N3 | 113.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2n···O2i | 0.86 | 1.92 | 2.749 (7) | 163 |
N4—H4n···O5ii | 0.86 | 1.93 | 2.754 (7) | 162 |
Symmetry codes: (i) −x+1, y+1/2, −z; (ii) −x+2, y+1/2, −z+1. |
As a part of our ongoing investigation on 4-formylbenzoate complexes (Deng et al., 2006a, 2006b, 2007), the title ZnII complex has been prepared and its structure is reported here. The molecular structure is shown in Fig. 1. The ZnII ion displays a tetrahedral coordination geometry (Table 1). Adjacent molecules are linked by N—H···O hydrogen bonds into a layer structure (Table 2 and Fig. 2).