Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113025614/wq3044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113025614/wq3044Isup2.hkl |
CCDC reference: 960968
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
[Zn(C8H6N4O3)] | F(000) = 544 |
Mr = 271.54 | Dx = 1.985 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.785 (2) Å | Cell parameters from 892 reflections |
b = 10.1308 (19) Å | θ = 3.2–29.0° |
c = 8.910 (3) Å | µ = 2.70 mm−1 |
β = 111.01 (3)° | T = 291 K |
V = 908.8 (4) Å3 | Prism, colourless |
Z = 4 | 0.20 × 0.12 × 0.08 mm |
Oxford Xcalibur Gemini diffractometer with Eos detector | 2941 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2237 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
Detector resolution: 16.2312 pixels mm-1 | θmax = 26.4°, θmin = 3.2° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2012) | k = −12→12 |
Tmin = 0.614, Tmax = 0.813 | l = −11→11 |
2941 measured reflections |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0672P)2] where P = (Fo2 + 2Fc2)/3 |
2941 reflections | (Δ/σ)max < 0.001 |
146 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.78 e Å−3 |
Experimental. CrysAlis PRO, Agilent Technologies, Version 1.171.36.20 (release 27–06-2012 CrysAlis171. NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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. Item _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. These statistics refer to single and composite reflections containing twin component 1 only. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.64942 (4) | 0.26247 (4) | 0.78290 (5) | 0.02551 (16) | |
O1 | 0.1125 (3) | −0.0691 (3) | 0.3944 (4) | 0.0463 (9) | |
O2 | −0.3078 (3) | 0.2088 (3) | 0.0857 (3) | 0.0322 (7) | |
O3 | −0.1937 (3) | 0.1663 (3) | −0.0675 (3) | 0.0294 (6) | |
N1 | 0.5004 (3) | 0.1375 (3) | 0.7029 (4) | 0.0280 (8) | |
N2 | 0.3858 (3) | −0.0526 (3) | 0.6707 (4) | 0.0288 (8) | |
N3 | 0.3506 (4) | 0.2617 (4) | 0.4777 (4) | 0.0408 (9) | |
N4 | 0.1644 (3) | 0.1354 (3) | 0.3244 (4) | 0.0290 (8) | |
C1 | 0.4928 (4) | 0.0163 (4) | 0.7555 (4) | 0.0265 (10) | |
H1 | 0.5584 | −0.0182 | 0.8462 | 0.032* | |
C2 | 0.3864 (4) | 0.1490 (4) | 0.5706 (4) | 0.0257 (9) | |
C3 | 0.3174 (4) | 0.0337 (4) | 0.5504 (4) | 0.0273 (9) | |
C4 | 0.1914 (4) | 0.0216 (5) | 0.4221 (5) | 0.0322 (10) | |
C5 | 0.2415 (4) | 0.2450 (5) | 0.3579 (6) | 0.0386 (10) | |
H5 | 0.2125 | 0.3153 | 0.2868 | 0.046* | |
C6 | 0.0441 (4) | 0.1323 (5) | 0.1776 (5) | 0.0394 (12) | |
H6A | 0.0414 | 0.0497 | 0.1216 | 0.047* | |
H6B | 0.0483 | 0.2036 | 0.1069 | 0.047* | |
C7 | −0.0817 (4) | 0.1461 (5) | 0.2149 (5) | 0.0347 (11) | |
H7A | −0.0960 | 0.0653 | 0.2648 | 0.042* | |
H7B | −0.0702 | 0.2172 | 0.2917 | 0.042* | |
C8 | −0.2015 (4) | 0.1738 (4) | 0.0695 (4) | 0.0249 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0213 (2) | 0.0284 (3) | 0.0203 (2) | 0.0012 (2) | −0.00048 (19) | 0.0004 (2) |
O1 | 0.0315 (17) | 0.0347 (19) | 0.053 (2) | −0.0031 (15) | −0.0082 (14) | 0.0016 (14) |
O2 | 0.0207 (14) | 0.0445 (19) | 0.0241 (17) | 0.0075 (13) | −0.0008 (11) | 0.0039 (12) |
O3 | 0.0270 (14) | 0.0416 (17) | 0.0166 (14) | 0.0078 (13) | 0.0041 (12) | 0.0010 (13) |
N1 | 0.0241 (17) | 0.0306 (19) | 0.0224 (19) | −0.0017 (14) | 0.0000 (15) | 0.0022 (14) |
N2 | 0.0256 (17) | 0.0296 (18) | 0.0215 (18) | −0.0015 (14) | −0.0033 (14) | 0.0021 (15) |
N3 | 0.0371 (19) | 0.042 (2) | 0.036 (2) | −0.008 (2) | 0.0045 (19) | 0.0101 (16) |
N4 | 0.0224 (19) | 0.035 (2) | 0.0214 (18) | 0.0008 (15) | −0.0023 (15) | 0.0042 (14) |
C1 | 0.0193 (18) | 0.033 (2) | 0.018 (2) | 0.0010 (17) | −0.0043 (15) | 0.0023 (16) |
C2 | 0.021 (2) | 0.032 (2) | 0.023 (2) | 0.0043 (17) | 0.0072 (17) | 0.0031 (17) |
C3 | 0.025 (2) | 0.036 (2) | 0.017 (2) | 0.0000 (17) | 0.0026 (17) | −0.0004 (16) |
C4 | 0.024 (2) | 0.038 (3) | 0.030 (3) | 0.002 (2) | 0.0037 (19) | −0.0023 (19) |
C5 | 0.033 (2) | 0.042 (3) | 0.034 (2) | 0.005 (2) | 0.003 (2) | 0.016 (2) |
C6 | 0.028 (2) | 0.063 (3) | 0.019 (2) | 0.004 (2) | −0.0025 (18) | 0.002 (2) |
C7 | 0.031 (2) | 0.046 (3) | 0.022 (2) | 0.006 (2) | 0.0033 (19) | 0.0033 (19) |
C8 | 0.024 (2) | 0.023 (2) | 0.022 (2) | 0.0019 (18) | 0.0023 (17) | 0.0015 (17) |
Zn1—N1 | 1.968 (3) | N3—C2 | 1.381 (5) |
Zn1—N2i | 1.984 (3) | N4—C5 | 1.354 (5) |
Zn1—O2ii | 1.992 (3) | N4—C4 | 1.411 (5) |
Zn1—O3iii | 1.993 (3) | N4—C6 | 1.476 (5) |
O1—C4 | 1.216 (5) | C1—H1 | 0.9300 |
O2—C8 | 1.257 (5) | C2—C3 | 1.361 (6) |
O2—Zn1iv | 1.992 (3) | C3—C4 | 1.433 (5) |
O3—C8 | 1.256 (4) | C5—H5 | 0.9300 |
O3—Zn1v | 1.993 (3) | C6—C7 | 1.514 (6) |
N1—C1 | 1.327 (5) | C6—H6A | 0.9700 |
N1—C2 | 1.370 (5) | C6—H6B | 0.9700 |
N2—C1 | 1.328 (5) | C7—C8 | 1.492 (5) |
N2—C3 | 1.375 (5) | C7—H7A | 0.9700 |
N2—Zn1vi | 1.984 (3) | C7—H7B | 0.9700 |
N3—C5 | 1.286 (5) | ||
N1—Zn1—N2i | 119.36 (13) | C2—C3—N2 | 109.1 (3) |
N1—Zn1—O2ii | 101.05 (13) | C2—C3—C4 | 119.7 (4) |
N2i—Zn1—O2ii | 99.67 (13) | N2—C3—C4 | 131.1 (4) |
N1—Zn1—O3iii | 108.35 (13) | O1—C4—N4 | 121.2 (3) |
N2i—Zn1—O3iii | 120.17 (12) | O1—C4—C3 | 128.4 (4) |
O2ii—Zn1—O3iii | 104.60 (12) | N4—C4—C3 | 110.4 (4) |
C8—O2—Zn1iv | 130.6 (3) | N3—C5—N4 | 126.7 (4) |
C8—O3—Zn1v | 106.5 (2) | N3—C5—H5 | 116.7 |
C1—N1—C2 | 103.4 (3) | N4—C5—H5 | 116.7 |
C1—N1—Zn1 | 127.8 (3) | N4—C6—C7 | 112.1 (3) |
C2—N1—Zn1 | 128.4 (3) | N4—C6—H6A | 109.2 |
C1—N2—C3 | 102.9 (3) | C7—C6—H6A | 109.2 |
C1—N2—Zn1vi | 124.8 (3) | N4—C6—H6B | 109.2 |
C3—N2—Zn1vi | 132.3 (3) | C7—C6—H6B | 109.2 |
C5—N3—C2 | 111.4 (4) | H6A—C6—H6B | 107.9 |
C5—N4—C4 | 124.0 (3) | C8—C7—C6 | 113.1 (4) |
C5—N4—C6 | 119.2 (4) | C8—C7—H7A | 109.0 |
C4—N4—C6 | 116.8 (4) | C6—C7—H7A | 109.0 |
N1—C1—N2 | 115.9 (3) | C8—C7—H7B | 109.0 |
N1—C1—H1 | 122.1 | C6—C7—H7B | 109.0 |
N2—C1—H1 | 122.1 | H7A—C7—H7B | 107.8 |
C3—C2—N1 | 108.7 (3) | O3—C8—O2 | 120.7 (3) |
C3—C2—N3 | 127.4 (4) | O3—C8—C7 | 119.6 (4) |
N1—C2—N3 | 123.9 (4) | O2—C8—C7 | 119.7 (4) |
N2i—Zn1—N1—C1 | −131.8 (3) | C1—N2—C3—C4 | −177.5 (4) |
O2ii—Zn1—N1—C1 | 120.4 (3) | Zn1vi—N2—C3—C4 | 4.7 (7) |
O3iii—Zn1—N1—C1 | 10.8 (4) | C5—N4—C4—O1 | 173.1 (4) |
N2i—Zn1—N1—C2 | 55.6 (4) | C6—N4—C4—O1 | −6.8 (6) |
O2ii—Zn1—N1—C2 | −52.2 (4) | C5—N4—C4—C3 | −6.0 (6) |
O3iii—Zn1—N1—C2 | −161.8 (3) | C6—N4—C4—C3 | 174.1 (4) |
C2—N1—C1—N2 | 0.3 (5) | C2—C3—C4—O1 | −173.7 (4) |
Zn1—N1—C1—N2 | −173.8 (3) | N2—C3—C4—O1 | 3.2 (8) |
C3—N2—C1—N1 | 0.1 (5) | C2—C3—C4—N4 | 5.3 (5) |
Zn1vi—N2—C1—N1 | 178.1 (3) | N2—C3—C4—N4 | −177.9 (4) |
C1—N1—C2—C3 | −0.5 (4) | C2—N3—C5—N4 | 2.6 (7) |
Zn1—N1—C2—C3 | 173.5 (3) | C4—N4—C5—N3 | 2.1 (8) |
C1—N1—C2—N3 | 178.7 (4) | C6—N4—C5—N3 | −178.0 (5) |
Zn1—N1—C2—N3 | −7.3 (6) | C5—N4—C6—C7 | −105.8 (5) |
C5—N3—C2—C3 | −3.1 (6) | C4—N4—C6—C7 | 74.1 (5) |
C5—N3—C2—N1 | 177.8 (4) | N4—C6—C7—C8 | 167.0 (4) |
N1—C2—C3—N2 | 0.6 (5) | Zn1v—O3—C8—O2 | 14.9 (4) |
N3—C2—C3—N2 | −178.6 (4) | Zn1v—O3—C8—C7 | −162.6 (3) |
N1—C2—C3—C4 | 178.1 (4) | Zn1iv—O2—C8—O3 | −177.2 (3) |
N3—C2—C3—C4 | −1.1 (7) | Zn1iv—O2—C8—C7 | 0.3 (6) |
C1—N2—C3—C2 | −0.4 (5) | C6—C7—C8—O3 | 9.1 (6) |
Zn1vi—N2—C3—C2 | −178.2 (3) | C6—C7—C8—O2 | −168.4 (4) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1, −y+1/2, z+1/2; (iii) x+1, y, z+1; (iv) x−1, −y+1/2, z−1/2; (v) x−1, y, z−1; (vi) −x+1, y−1/2, −z+3/2. |