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metal-organic compounds
The Zr atom in the title salt, (C10H10N2)2[Zr(C2O4)4], is chelated by four oxalate anions in a square-antiprismatic geometry. The cations and anions are linked by short N—HO and long C—HO hydrogen bonds into a layer structure. The Zr atom lies on a special position of site symmetry 2.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033829/bt6767sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033829/bt6767Isup2.hkl |
CCDC reference: 289662
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.047
- wR factor = 0.112
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.470 0.966 Tmin(prime) and Tmax expected: 0.913 0.966 RR(prime) = 0.515 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.51
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.21 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.53 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C3 - C4 ... 1.54 Ang. PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.850(10) ...... 3.00 su-Rat N1 -H1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.860(10) ...... 3.00 su-Rat N2 -H2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.850(10) ...... 3.00 su-Rat N1 -H1 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.860(10) ...... 3.00 su-Rat N2 -H2 1.555 1.555
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
(C10H10N2)2[Zr(C2O4)4] | F(000) = 1536 |
Mr = 759.70 | Dx = 1.831 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1612 reflections |
a = 19.447 (2) Å | θ = 2.2–23.1° |
b = 10.986 (1) Å | µ = 0.49 mm−1 |
c = 15.084 (2) Å | T = 295 K |
β = 121.231 (2)° | Plate, colorless |
V = 2755.6 (5) Å3 | 0.18 × 0.16 × 0.07 mm |
Z = 4 |
Data collection top
Bruker APEX area-detector diffractometer | 3097 independent reflections |
Radiation source: fine-focus sealed tube | 2340 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
φ and ω scans | θmax = 27.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −25→13 |
Tmin = 0.470, Tmax = 0.966 | k = −14→12 |
7967 measured reflections | l = −19→19 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0564P)2 + 0.727P] where P = (Fo2 + 2Fc2)/3 |
3097 reflections | (Δ/σ)max = 0.001 |
230 parameters | Δρmax = 0.65 e Å−3 |
2 restraints | Δρmin = −0.60 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Zr1 | 0.5000 | 0.29208 (4) | 0.2500 | 0.0219 (2) | |
O1 | 0.4320 (1) | 0.4489 (2) | 0.1533 (2) | 0.0355 (6) | |
O2 | 0.4563 (2) | 0.6300 (2) | 0.1042 (2) | 0.0495 (7) | |
O3 | 0.5534 (2) | 0.3521 (2) | 0.1605 (2) | 0.0369 (6) | |
O4 | 0.5859 (2) | 0.5189 (2) | 0.1072 (2) | 0.0387 (6) | |
O5 | 0.6256 (1) | 0.2302 (2) | 0.3295 (2) | 0.0364 (6) | |
O6 | 0.7017 (2) | 0.0629 (2) | 0.3810 (2) | 0.0440 (7) | |
O7 | 0.5152 (1) | 0.1318 (2) | 0.3486 (2) | 0.0304 (6) | |
O8 | 0.5773 (2) | −0.0502 (2) | 0.3870 (2) | 0.0425 (7) | |
N1 | 0.6068 (2) | 0.7576 (3) | 0.1035 (3) | 0.0353 (7) | |
N2 | 0.7780 (2) | 1.3220 (3) | 0.1246 (2) | 0.0352 (7) | |
C1 | 0.4708 (2) | 0.5230 (3) | 0.1276 (3) | 0.0323 (8) | |
C2 | 0.5430 (2) | 0.4623 (3) | 0.1305 (3) | 0.0295 (8) | |
C3 | 0.6403 (2) | 0.1196 (3) | 0.3590 (3) | 0.0283 (8) | |
C4 | 0.5721 (2) | 0.0581 (3) | 0.3659 (3) | 0.0292 (8) | |
C5 | 0.6767 (2) | 0.7619 (3) | 0.1059 (3) | 0.0395 (9) | |
C6 | 0.7129 (2) | 0.8711 (3) | 0.1152 (3) | 0.0342 (8) | |
C7 | 0.6780 (2) | 0.9789 (3) | 0.1208 (2) | 0.0265 (7) | |
C8 | 0.6058 (2) | 0.9689 (3) | 0.1186 (3) | 0.0328 (8) | |
C9 | 0.5709 (2) | 0.8578 (4) | 0.1097 (3) | 0.0381 (9) | |
C10 | 0.8195 (2) | 1.2217 (3) | 0.1338 (3) | 0.0381 (9) | |
C11 | 0.7889 (2) | 1.1096 (3) | 0.1342 (3) | 0.0343 (9) | |
C12 | 0.7147 (2) | 1.0997 (3) | 0.1258 (3) | 0.0270 (8) | |
C13 | 0.6742 (2) | 1.2072 (3) | 0.1184 (3) | 0.0368 (9) | |
C14 | 0.7072 (2) | 1.3172 (3) | 0.1168 (3) | 0.0391 (9) | |
H1 | 0.586 (2) | 0.688 (2) | 0.095 (3) | 0.04 (1)* | |
H2 | 0.797 (2) | 1.391 (2) | 0.122 (3) | 0.06 (2)* | |
H5 | 0.7003 | 0.6904 | 0.1013 | 0.047* | |
H6 | 0.7617 | 0.8735 | 0.1177 | 0.041* | |
H8 | 0.5808 | 1.0388 | 0.1233 | 0.039* | |
H9 | 0.5225 | 0.8523 | 0.1080 | 0.046* | |
H10 | 0.8695 | 1.2278 | 0.1399 | 0.046* | |
H11 | 0.8181 | 1.0397 | 0.1402 | 0.041* | |
H13 | 0.6249 | 1.2046 | 0.1146 | 0.044* | |
H14 | 0.6794 | 1.3889 | 0.1102 | 0.047* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zr1 | 0.0202 (3) | 0.0165 (2) | 0.0348 (3) | 0.000 | 0.0184 (2) | 0.000 |
O1 | 0.029 (1) | 0.035 (2) | 0.050 (2) | 0.010 (1) | 0.025 (1) | 0.013 (1) |
O2 | 0.064 (2) | 0.031 (2) | 0.074 (2) | 0.022 (1) | 0.049 (2) | 0.018 (1) |
O3 | 0.047 (2) | 0.023 (1) | 0.063 (2) | 0.012 (1) | 0.044 (2) | 0.013 (1) |
O4 | 0.043 (2) | 0.030 (2) | 0.060 (2) | 0.003 (1) | 0.038 (2) | 0.008 (1) |
O5 | 0.023 (1) | 0.021 (1) | 0.063 (2) | 0.002 (1) | 0.022 (1) | 0.009 (1) |
O6 | 0.029 (2) | 0.031 (2) | 0.074 (2) | 0.008 (1) | 0.028 (2) | 0.011 (1) |
O7 | 0.028 (1) | 0.031 (1) | 0.038 (1) | −0.001 (1) | 0.021 (1) | 0.006 (1) |
O8 | 0.044 (2) | 0.029 (2) | 0.056 (2) | 0.001 (1) | 0.027 (1) | 0.015 (1) |
N1 | 0.041 (2) | 0.025 (2) | 0.043 (2) | 0.001 (1) | 0.023 (2) | 0.005 (1) |
N2 | 0.038 (2) | 0.025 (2) | 0.040 (2) | −0.006 (1) | 0.019 (2) | −0.006 (1) |
C1 | 0.034 (2) | 0.030 (2) | 0.036 (2) | 0.007 (2) | 0.021 (2) | 0.005 (2) |
C2 | 0.034 (2) | 0.020 (2) | 0.040 (2) | 0.004 (2) | 0.023 (2) | 0.003 (2) |
C3 | 0.026 (2) | 0.022 (2) | 0.035 (2) | 0.000 (1) | 0.014 (2) | 0.001 (2) |
C4 | 0.026 (2) | 0.028 (2) | 0.030 (2) | −0.001 (2) | 0.012 (2) | 0.005 (1) |
C5 | 0.044 (2) | 0.028 (2) | 0.054 (2) | 0.013 (2) | 0.031 (2) | 0.006 (2) |
C6 | 0.029 (2) | 0.030 (2) | 0.049 (2) | 0.007 (2) | 0.024 (2) | 0.001 (2) |
C7 | 0.024 (2) | 0.029 (2) | 0.025 (2) | 0.005 (1) | 0.012 (2) | 0.003 (1) |
C8 | 0.036 (2) | 0.026 (2) | 0.044 (2) | 0.005 (2) | 0.026 (2) | 0.001 (2) |
C9 | 0.035 (2) | 0.039 (2) | 0.050 (2) | 0.003 (2) | 0.029 (2) | 0.006 (2) |
C10 | 0.031 (2) | 0.039 (2) | 0.047 (2) | −0.004 (2) | 0.022 (2) | −0.007 (2) |
C11 | 0.026 (2) | 0.031 (2) | 0.045 (2) | 0.002 (2) | 0.018 (2) | −0.005 (2) |
C12 | 0.027 (2) | 0.026 (2) | 0.026 (2) | 0.001 (1) | 0.012 (2) | −0.001 (1) |
C13 | 0.029 (2) | 0.027 (2) | 0.058 (2) | 0.003 (2) | 0.025 (2) | −0.006 (2) |
C14 | 0.035 (2) | 0.026 (2) | 0.057 (3) | 0.005 (2) | 0.024 (2) | −0.002 (2) |
Geometric parameters (Å, º) top
Zr1—O1 | 2.201 (2) | C3—C4 | 1.539 (5) |
Zr1—O1i | 2.201 (2) | C5—C6 | 1.361 (5) |
Zr1—O3 | 2.189 (2) | C6—C7 | 1.390 (5) |
Zr1—O3i | 2.189 (2) | C7—C8 | 1.392 (5) |
Zr1—O5 | 2.197 (2) | C7—C12 | 1.490 (5) |
Zr1—O5i | 2.197 (2) | C8—C9 | 1.368 (5) |
Zr1—O7 | 2.223 (2) | C10—C11 | 1.370 (5) |
Zr1—O7i | 2.223 (2) | C11—C12 | 1.387 (5) |
O1—C1 | 1.299 (4) | C12—C13 | 1.391 (5) |
O2—C1 | 1.218 (4) | C13—C14 | 1.374 (5) |
O3—C2 | 1.271 (4) | N1—H1 | 0.85 (1) |
O4—C2 | 1.228 (4) | N2—H2 | 0.86 (1) |
O5—C3 | 1.275 (4) | C5—H5 | 0.93 |
O6—C3 | 1.229 (4) | C6—H6 | 0.93 |
O7—C4 | 1.284 (4) | C8—H8 | 0.93 |
O8—C4 | 1.222 (4) | C9—H9 | 0.93 |
N1—C9 | 1.333 (5) | C10—H10 | 0.93 |
N1—C5 | 1.340 (5) | C11—H11 | 0.93 |
N2—C14 | 1.322 (5) | C13—H13 | 0.93 |
N2—C10 | 1.330 (5) | C14—H14 | 0.93 |
C1—C2 | 1.535 (5) | ||
O1—Zr1—O1i | 76.9 (1) | N1—C5—C6 | 119.8 (3) |
O1—Zr1—O3 | 70.7 (1) | C5—C6—C7 | 120.9 (3) |
O1—Zr1—O3i | 81.9 (1) | C6—C7—C8 | 116.8 (3) |
O1—Zr1—O5 | 136.0 (1) | C6—C7—C12 | 121.8 (3) |
O1—Zr1—O5i | 76.4 (1) | C8—C7—C12 | 121.4 (3) |
O1—Zr1—O7 | 152.8 (1) | C9—C8—C7 | 121.0 (3) |
O1—Zr1—O7i | 110.6 (1) | N1—C9—C8 | 119.6 (3) |
O3—Zr1—O3i | 144.9 (1) | N2—C10—C11 | 120.3 (3) |
O3—Zr1—O5 | 71.4 (1) | C10—C11—C12 | 120.2 (3) |
O3—Zr1—O5i | 120.3 (1) | C11—C12—C13 | 117.4 (3) |
O3—Zr1—O7 | 135.2 (1) | C11—C12—C7 | 121.5 (3) |
O3—Zr1—O7i | 76.5 (1) | C13—C12—C7 | 121.1 (3) |
O5—Zr1—O5i | 144.0 (1) | C14—C13—C12 | 119.9 (3) |
O5—Zr1—O7 | 70.4 (1) | N2—C14—C13 | 120.5 (3) |
O5—Zr1—O7i | 81.1 (1) | C9—N1—H1 | 122 (3) |
O7—Zr1—O7i | 75.3 (1) | C5—N1—H1 | 116 (3) |
C1—O1—Zr1 | 116.5 (2) | C14—N2—H2 | 120 (3) |
C2—O3—Zr1 | 117.9 (2) | C10—N2—H2 | 119 (3) |
C3—O5—Zr1 | 118.0 (2) | N1—C5—H5 | 120.1 |
C4—O7—Zr1 | 116.0 (2) | C6—C5—H5 | 120.1 |
C9—N1—C5 | 121.9 (3) | C5—C6—H6 | 119.5 |
C14—N2—C10 | 121.7 (3) | C7—C6—H6 | 119.5 |
O2—C1—O1 | 127.4 (3) | C9—C8—H8 | 119.5 |
O2—C1—C2 | 120.0 (3) | C7—C8—H8 | 119.5 |
O1—C1—C2 | 112.6 (3) | N1—C9—H9 | 120.2 |
O4—C2—O3 | 125.3 (3) | C8—C9—H9 | 120.2 |
O4—C2—C1 | 121.2 (3) | N2—C10—H10 | 119.9 |
O3—C2—C1 | 113.4 (3) | C11—C10—H10 | 119.9 |
O6—C3—O5 | 126.0 (3) | C10—C11—H11 | 119.9 |
O6—C3—C4 | 120.6 (3) | C12—C11—H11 | 119.9 |
O5—C3—C4 | 113.4 (3) | C14—C13—H13 | 120.0 |
O8—C4—O7 | 127.8 (3) | C12—C13—H13 | 120.0 |
O8—C4—C3 | 119.2 (3) | N2—C14—H14 | 119.7 |
O7—C4—C3 | 113.0 (3) | C13—C14—H14 | 119.7 |
O3i—Zr1—O1—C1 | 132.1 (3) | O2—C1—C2—O4 | −1.6 (6) |
O3—Zr1—O1—C1 | −25.7 (2) | O1—C1—C2—O4 | 179.2 (3) |
O5i—Zr1—O1—C1 | −155.2 (3) | O2—C1—C2—O3 | 177.1 (3) |
O5—Zr1—O1—C1 | 6.1 (3) | O1—C1—C2—O3 | −2.1 (5) |
O1i—Zr1—O1—C1 | 60.1 (2) | Zr1—O5—C3—O6 | 161.3 (3) |
O7i—Zr1—O1—C1 | −92.5 (3) | Zr1—O5—C3—C4 | −18.8 (4) |
O7—Zr1—O1—C1 | 169.8 (2) | Zr1—O7—C4—O8 | −154.5 (3) |
O3i—Zr1—O3—C2 | −15.7 (2) | Zr1—O7—C4—C3 | 26.0 (3) |
O5i—Zr1—O3—C2 | 85.3 (3) | O6—C3—C4—O8 | −4.8 (5) |
O5—Zr1—O3—C2 | −132.4 (3) | O5—C3—C4—O8 | 175.3 (3) |
O1i—Zr1—O3—C2 | −54.1 (3) | O6—C3—C4—O7 | 174.8 (3) |
O1—Zr1—O3—C2 | 24.9 (3) | O5—C3—C4—O7 | −5.1 (4) |
O7i—Zr1—O3—C2 | 142.7 (3) | C9—N1—C5—C6 | 0.1 (6) |
O7—Zr1—O3—C2 | −165.1 (2) | N1—C5—C6—C7 | −0.9 (6) |
O3i—Zr1—O5—C3 | 84.5 (3) | C5—C6—C7—C8 | 1.3 (5) |
O3—Zr1—O5—C3 | −132.1 (3) | C5—C6—C7—C12 | −177.0 (3) |
O5i—Zr1—O5—C3 | −15.7 (2) | C6—C7—C8—C9 | −1.0 (5) |
O1i—Zr1—O5—C3 | 142.1 (3) | C12—C7—C8—C9 | 177.3 (3) |
O1—Zr1—O5—C3 | −163.8 (2) | C5—N1—C9—C8 | 0.1 (6) |
O7i—Zr1—O5—C3 | −53.3 (3) | C7—C8—C9—N1 | 0.3 (6) |
O7—Zr1—O5—C3 | 24.1 (2) | C14—N2—C10—C11 | 0.7 (6) |
O3i—Zr1—O7—C4 | −156.3 (2) | N2—C10—C11—C12 | −0.4 (6) |
O3—Zr1—O7—C4 | 6.2 (3) | C10—C11—C12—C13 | −0.8 (5) |
O5i—Zr1—O7—C4 | 130.8 (2) | C10—C11—C12—C7 | 176.9 (3) |
O5—Zr1—O7—C4 | −26.8 (2) | C6—C7—C12—C11 | −5.7 (5) |
O1i—Zr1—O7—C4 | −93.2 (2) | C8—C7—C12—C11 | 176.1 (3) |
O1—Zr1—O7—C4 | 165.2 (2) | C6—C7—C12—C13 | 171.9 (3) |
O7i—Zr1—O7—C4 | 58.8 (2) | C8—C7—C12—C13 | −6.3 (5) |
Zr1—O1—C1—O2 | −155.4 (3) | C11—C12—C13—C14 | 1.7 (5) |
Zr1—O1—C1—C2 | 23.7 (4) | C7—C12—C13—C14 | −176.0 (3) |
Zr1—O3—C2—O4 | 157.8 (3) | C10—N2—C14—C13 | 0.3 (6) |
Zr1—O3—C2—C1 | −20.8 (4) | C12—C13—C14—N2 | −1.5 (6) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4 | 0.85 (1) | 1.86 (2) | 2.658 (4) | 155 (4) |
N2—H2···O6ii | 0.86 (1) | 1.89 (2) | 2.683 (4) | 154 (4) |
C5—H5···O6iii | 0.93 | 2.27 | 3.152 (5) | 159 |
C6—H6···O5iii | 0.93 | 2.47 | 3.199 (4) | 135 |
C8—H8···O7iv | 0.93 | 2.35 | 3.193 (4) | 150 |
C9—H9···O8iv | 0.93 | 2.25 | 3.078 (4) | 148 |
C10—H10···O2v | 0.93 | 2.29 | 3.085 (5) | 144 |
C11—H11···O1v | 0.93 | 2.34 | 3.179 (4) | 150 |
C13—H13···O3vi | 0.93 | 2.46 | 3.163 (4) | 133 |
C14—H14···O4vi | 0.93 | 2.29 | 3.184 (4) | 160 |
Symmetry codes: (ii) −x+3/2, y+3/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) −x+1, y+1, −z+1/2; (v) x+1/2, y+1/2, z; (vi) x, y+1, z. |
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