Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010999/zl2006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010999/zl2006Isup2.hkl |
CCDC reference: 643681
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.097
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: XSCANS (Bruker, 2001); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
[Cu(C8H4O5)(C10H8N2)] | F(000) = 860 |
Mr = 423.86 | Dx = 1.616 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.007 (2) Å | Cell parameters from 23 reflections |
b = 15.251 (4) Å | θ = 2.7–14.4° |
c = 11.5785 (17) Å | µ = 1.29 mm−1 |
β = 99.599 (14)° | T = 293 K |
V = 1742.4 (6) Å3 | Block, colorless |
Z = 4 | 0.37 × 0.32 × 0.27 mm |
Bruker P4 diffractometer | 3555 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
ω scans | h = −12→1 |
Absorption correction: ψ scan (North et al., 1968) | k = −19→1 |
Tmin = 0.648, Tmax = 0.724 | l = −14→15 |
5002 measured reflections | 3 standard reflections every 97 reflections |
3987 independent reflections | intensity decay: none |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0576P)2 + 0.5015P] where P = (Fo2 + 2Fc2)/3 |
3987 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
Experimental. SHELXTL Reference Manual, Siemens Industrial Automation,Inc., 1994' |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.08407 (2) | 0.024482 (14) | 0.745297 (19) | 0.02733 (9) | |
C1 | −0.08662 (18) | 0.15441 (13) | 0.77950 (17) | 0.0304 (4) | |
C2 | −0.16083 (18) | 0.21309 (12) | 0.85242 (17) | 0.0287 (4) | |
C3 | −0.12890 (19) | 0.21034 (12) | 0.97398 (17) | 0.0310 (4) | |
H3A | −0.0656 | 0.1700 | 1.0099 | 0.037* | |
C4 | −0.1912 (2) | 0.26779 (13) | 1.04233 (17) | 0.0343 (4) | |
C5 | −0.28763 (19) | 0.32682 (12) | 0.98867 (17) | 0.0320 (4) | |
H5A | −0.3284 | 0.3659 | 1.0338 | 0.038* | |
C6 | −0.32299 (18) | 0.32739 (12) | 0.86757 (16) | 0.0281 (4) | |
C7 | −0.25925 (19) | 0.27096 (12) | 0.79922 (16) | 0.0297 (4) | |
H7A | −0.2826 | 0.2721 | 0.7181 | 0.036* | |
C8 | −0.42771 (18) | 0.39034 (12) | 0.80898 (16) | 0.0281 (4) | |
C9 | 0.2130 (2) | −0.07729 (14) | 0.56790 (18) | 0.0388 (4) | |
H9A | 0.1262 | −0.0916 | 0.5304 | 0.047* | |
C10 | 0.3244 (3) | −0.10945 (17) | 0.5228 (2) | 0.0504 (6) | |
H10A | 0.3112 | −0.1451 | 0.4567 | 0.060* | |
C11 | 0.4531 (3) | −0.08854 (17) | 0.5759 (2) | 0.0525 (6) | |
H11A | 0.5275 | −0.1095 | 0.5458 | 0.063* | |
C12 | 0.4718 (2) | −0.03522 (15) | 0.6760 (2) | 0.0425 (5) | |
C13 | 0.6008 (2) | −0.00800 (19) | 0.7377 (2) | 0.0507 (6) | |
H13A | 0.6791 | −0.0264 | 0.7115 | 0.061* | |
C14 | 0.6113 (2) | 0.04390 (17) | 0.8333 (3) | 0.0500 (6) | |
H14A | 0.6967 | 0.0593 | 0.8729 | 0.060* | |
C15 | 0.4937 (2) | 0.07549 (14) | 0.8748 (2) | 0.0412 (5) | |
C16 | 0.4954 (3) | 0.13224 (17) | 0.9705 (2) | 0.0515 (6) | |
H16A | 0.5776 | 0.1517 | 1.0122 | 0.062* | |
C17 | 0.3769 (3) | 0.15884 (19) | 1.0023 (2) | 0.0578 (7) | |
H17A | 0.3776 | 0.1967 | 1.0654 | 0.069* | |
C18 | 0.2540 (2) | 0.12874 (17) | 0.9394 (2) | 0.0510 (6) | |
H18A | 0.1736 | 0.1473 | 0.9618 | 0.061* | |
C19 | 0.3657 (2) | 0.04922 (13) | 0.81644 (18) | 0.0336 (4) | |
C20 | 0.3543 (2) | −0.00615 (13) | 0.71579 (18) | 0.0322 (4) | |
N1 | 0.22717 (17) | −0.02698 (10) | 0.66256 (15) | 0.0319 (3) | |
N2 | 0.24789 (17) | 0.07461 (12) | 0.84875 (16) | 0.0362 (4) | |
O1 | −0.07652 (19) | 0.17430 (11) | 0.67881 (14) | 0.0485 (4) | |
O2 | −0.03444 (14) | 0.08566 (9) | 0.83212 (13) | 0.0359 (3) | |
O3 | −0.1598 (2) | 0.26896 (13) | 1.16103 (13) | 0.0582 (5) | |
H3B | −0.1105 | 0.2272 | 1.1833 | 0.087* | |
O4 | −0.43805 (14) | 0.46356 (9) | 0.85927 (13) | 0.0325 (3) | |
O5 | −0.50007 (15) | 0.37104 (10) | 0.71426 (13) | 0.0405 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.02539 (14) | 0.02328 (13) | 0.03273 (14) | 0.00032 (8) | 0.00316 (9) | −0.00318 (8) |
C1 | 0.0290 (9) | 0.0270 (9) | 0.0349 (9) | 0.0008 (7) | 0.0041 (7) | −0.0035 (7) |
C2 | 0.0286 (8) | 0.0248 (8) | 0.0325 (9) | 0.0008 (7) | 0.0045 (7) | −0.0019 (7) |
C3 | 0.0325 (9) | 0.0256 (9) | 0.0331 (9) | 0.0058 (7) | 0.0005 (7) | 0.0012 (7) |
C4 | 0.0394 (10) | 0.0324 (10) | 0.0292 (9) | 0.0046 (8) | 0.0000 (8) | −0.0009 (7) |
C5 | 0.0360 (10) | 0.0272 (9) | 0.0321 (9) | 0.0067 (7) | 0.0037 (7) | −0.0041 (7) |
C6 | 0.0278 (8) | 0.0225 (8) | 0.0326 (9) | 0.0012 (6) | 0.0012 (7) | −0.0003 (7) |
C7 | 0.0328 (9) | 0.0276 (8) | 0.0275 (8) | 0.0033 (7) | 0.0017 (7) | 0.0012 (7) |
C8 | 0.0265 (8) | 0.0246 (8) | 0.0323 (9) | 0.0007 (7) | 0.0024 (7) | 0.0016 (7) |
C9 | 0.0422 (11) | 0.0365 (10) | 0.0372 (10) | 0.0022 (9) | 0.0048 (8) | −0.0052 (8) |
C10 | 0.0581 (14) | 0.0475 (13) | 0.0481 (13) | 0.0069 (11) | 0.0163 (11) | −0.0139 (10) |
C11 | 0.0471 (13) | 0.0508 (14) | 0.0643 (15) | 0.0102 (11) | 0.0234 (12) | −0.0088 (12) |
C12 | 0.0348 (11) | 0.0368 (11) | 0.0584 (14) | 0.0043 (8) | 0.0150 (10) | −0.0013 (10) |
C13 | 0.0302 (11) | 0.0482 (13) | 0.0752 (18) | 0.0022 (9) | 0.0134 (11) | −0.0003 (12) |
C14 | 0.0276 (10) | 0.0450 (12) | 0.0753 (17) | −0.0074 (9) | 0.0021 (10) | 0.0020 (12) |
C15 | 0.0339 (10) | 0.0355 (10) | 0.0526 (12) | −0.0094 (8) | 0.0022 (9) | 0.0023 (9) |
C16 | 0.0439 (12) | 0.0477 (13) | 0.0591 (14) | −0.0169 (11) | −0.0028 (11) | −0.0113 (11) |
C17 | 0.0548 (14) | 0.0567 (15) | 0.0599 (15) | −0.0133 (12) | 0.0034 (12) | −0.0293 (13) |
C18 | 0.0446 (12) | 0.0522 (14) | 0.0562 (14) | −0.0064 (10) | 0.0086 (10) | −0.0267 (12) |
C19 | 0.0307 (9) | 0.0280 (9) | 0.0417 (10) | −0.0045 (7) | 0.0052 (8) | −0.0013 (8) |
C20 | 0.0288 (9) | 0.0267 (8) | 0.0417 (10) | 0.0001 (7) | 0.0071 (8) | 0.0010 (8) |
N1 | 0.0329 (8) | 0.0270 (8) | 0.0359 (8) | 0.0003 (6) | 0.0064 (7) | −0.0025 (6) |
N2 | 0.0322 (8) | 0.0342 (8) | 0.0423 (9) | −0.0047 (7) | 0.0063 (7) | −0.0097 (7) |
O1 | 0.0719 (11) | 0.0391 (8) | 0.0385 (8) | 0.0143 (8) | 0.0209 (8) | 0.0039 (7) |
O2 | 0.0367 (7) | 0.0324 (7) | 0.0387 (7) | 0.0110 (6) | 0.0062 (6) | −0.0004 (6) |
O3 | 0.0820 (13) | 0.0613 (11) | 0.0272 (7) | 0.0353 (10) | −0.0025 (8) | −0.0032 (7) |
O4 | 0.0310 (7) | 0.0253 (6) | 0.0388 (7) | 0.0043 (5) | −0.0016 (6) | −0.0032 (5) |
O5 | 0.0442 (8) | 0.0333 (7) | 0.0382 (8) | 0.0044 (6) | −0.0102 (6) | −0.0029 (6) |
Cu1—O2 | 1.9197 (14) | C10—C11 | 1.368 (4) |
Cu1—O4i | 1.9683 (14) | C10—H10A | 0.9300 |
Cu1—N1 | 2.0105 (17) | C11—C12 | 1.403 (4) |
Cu1—N2 | 2.0129 (17) | C11—H11A | 0.9300 |
C1—O1 | 1.225 (2) | C12—C20 | 1.404 (3) |
C1—O2 | 1.280 (2) | C12—C13 | 1.428 (3) |
C1—C2 | 1.508 (3) | C13—C14 | 1.351 (4) |
C2—C7 | 1.388 (3) | C13—H13A | 0.9300 |
C2—C3 | 1.391 (3) | C14—C15 | 1.427 (3) |
C3—C4 | 1.395 (3) | C14—H14A | 0.9300 |
C3—H3A | 0.9300 | C15—C19 | 1.403 (3) |
C4—O3 | 1.358 (2) | C15—C16 | 1.404 (3) |
C4—C5 | 1.388 (3) | C16—C17 | 1.361 (4) |
C5—C6 | 1.388 (3) | C16—H16A | 0.9300 |
C5—H5A | 0.9300 | C17—C18 | 1.399 (3) |
C6—C7 | 1.394 (3) | C17—H17A | 0.9300 |
C6—C8 | 1.498 (2) | C18—N2 | 1.328 (3) |
C7—H7A | 0.9300 | C18—H18A | 0.9300 |
C8—O5 | 1.245 (2) | C19—N2 | 1.352 (3) |
C8—O4 | 1.272 (2) | C19—C20 | 1.428 (3) |
C9—N1 | 1.326 (3) | C20—N1 | 1.356 (3) |
C9—C10 | 1.397 (3) | O3—H3B | 0.8200 |
C9—H9A | 0.9300 | O4—Cu1ii | 1.9683 (14) |
O2—Cu1—O4i | 95.25 (6) | C12—C11—H11A | 120.2 |
O2—Cu1—N1 | 172.13 (7) | C20—C12—C11 | 116.7 (2) |
O4i—Cu1—N1 | 92.14 (7) | C20—C12—C13 | 118.7 (2) |
O2—Cu1—N2 | 90.96 (7) | C11—C12—C13 | 124.6 (2) |
O4i—Cu1—N2 | 173.08 (6) | C14—C13—C12 | 121.4 (2) |
N1—Cu1—N2 | 81.82 (7) | C14—C13—H13A | 119.3 |
O1—C1—O2 | 124.35 (18) | C12—C13—H13A | 119.3 |
O1—C1—C2 | 120.82 (17) | C13—C14—C15 | 121.2 (2) |
O2—C1—C2 | 114.81 (17) | C13—C14—H14A | 119.4 |
C7—C2—C3 | 119.64 (17) | C15—C14—H14A | 119.4 |
C7—C2—C1 | 120.54 (17) | C19—C15—C16 | 116.5 (2) |
C3—C2—C1 | 119.81 (16) | C19—C15—C14 | 118.6 (2) |
C2—C3—C4 | 120.40 (17) | C16—C15—C14 | 124.9 (2) |
C2—C3—H3A | 119.8 | C17—C16—C15 | 120.0 (2) |
C4—C3—H3A | 119.8 | C17—C16—H16A | 120.0 |
O3—C4—C5 | 118.08 (18) | C15—C16—H16A | 120.0 |
O3—C4—C3 | 122.17 (18) | C16—C17—C18 | 119.4 (2) |
C5—C4—C3 | 119.75 (17) | C16—C17—H17A | 120.3 |
C6—C5—C4 | 119.82 (17) | C18—C17—H17A | 120.3 |
C6—C5—H5A | 120.1 | N2—C18—C17 | 122.4 (2) |
C4—C5—H5A | 120.1 | N2—C18—H18A | 118.8 |
C5—C6—C7 | 120.41 (17) | C17—C18—H18A | 118.8 |
C5—C6—C8 | 120.19 (16) | N2—C19—C15 | 123.6 (2) |
C7—C6—C8 | 119.38 (16) | N2—C19—C20 | 116.15 (17) |
C2—C7—C6 | 119.93 (17) | C15—C19—C20 | 120.26 (19) |
C2—C7—H7A | 120.0 | N1—C20—C12 | 123.4 (2) |
C6—C7—H7A | 120.0 | N1—C20—C19 | 116.77 (17) |
O5—C8—O4 | 122.10 (17) | C12—C20—C19 | 119.80 (19) |
O5—C8—C6 | 120.52 (17) | C9—N1—C20 | 118.31 (18) |
O4—C8—C6 | 117.38 (16) | C9—N1—Cu1 | 129.28 (15) |
N1—C9—C10 | 122.0 (2) | C20—N1—Cu1 | 112.40 (13) |
N1—C9—H9A | 119.0 | C18—N2—C19 | 117.99 (19) |
C10—C9—H9A | 119.0 | C18—N2—Cu1 | 129.17 (16) |
C11—C10—C9 | 120.0 (2) | C19—N2—Cu1 | 112.83 (13) |
C11—C10—H10A | 120.0 | C1—O2—Cu1 | 112.81 (12) |
C9—C10—H10A | 120.0 | C4—O3—H3B | 109.5 |
C10—C11—C12 | 119.5 (2) | C8—O4—Cu1ii | 103.98 (12) |
C10—C11—H11A | 120.2 | ||
O1—C1—C2—C7 | 24.1 (3) | C14—C15—C19—C20 | −1.6 (3) |
O2—C1—C2—C7 | −157.51 (17) | C11—C12—C20—N1 | −0.1 (3) |
O1—C1—C2—C3 | −154.8 (2) | C13—C12—C20—N1 | 178.9 (2) |
O2—C1—C2—C3 | 23.6 (3) | C11—C12—C20—C19 | −179.3 (2) |
C7—C2—C3—C4 | −2.6 (3) | C13—C12—C20—C19 | −0.3 (3) |
C1—C2—C3—C4 | 176.31 (18) | N2—C19—C20—N1 | 0.5 (3) |
C2—C3—C4—O3 | −178.0 (2) | C15—C19—C20—N1 | −178.48 (19) |
C2—C3—C4—C5 | 1.3 (3) | N2—C19—C20—C12 | 179.7 (2) |
O3—C4—C5—C6 | −179.7 (2) | C15—C19—C20—C12 | 0.8 (3) |
C3—C4—C5—C6 | 1.0 (3) | C10—C9—N1—C20 | 0.5 (3) |
C4—C5—C6—C7 | −2.0 (3) | C10—C9—N1—Cu1 | −178.49 (17) |
C4—C5—C6—C8 | 179.52 (18) | C12—C20—N1—C9 | −0.1 (3) |
C3—C2—C7—C6 | 1.6 (3) | C19—C20—N1—C9 | 179.08 (18) |
C1—C2—C7—C6 | −177.32 (17) | C12—C20—N1—Cu1 | 179.02 (17) |
C5—C6—C7—C2 | 0.7 (3) | C19—C20—N1—Cu1 | −1.8 (2) |
C8—C6—C7—C2 | 179.19 (17) | O4i—Cu1—N1—C9 | 4.21 (18) |
C5—C6—C8—O5 | −150.24 (19) | N2—Cu1—N1—C9 | −179.18 (19) |
C7—C6—C8—O5 | 31.3 (3) | O4i—Cu1—N1—C20 | −174.81 (14) |
C5—C6—C8—O4 | 30.4 (3) | N2—Cu1—N1—C20 | 1.79 (14) |
C7—C6—C8—O4 | −148.06 (18) | C17—C18—N2—C19 | −0.9 (4) |
N1—C9—C10—C11 | −0.7 (4) | C17—C18—N2—Cu1 | −179.2 (2) |
C9—C10—C11—C12 | 0.4 (4) | C15—C19—N2—C18 | 1.4 (3) |
C10—C11—C12—C20 | −0.1 (4) | C20—C19—N2—C18 | −177.6 (2) |
C10—C11—C12—C13 | −179.0 (3) | C15—C19—N2—Cu1 | 179.98 (17) |
C20—C12—C13—C14 | 0.7 (4) | C20—C19—N2—Cu1 | 1.0 (2) |
C11—C12—C13—C14 | 179.6 (3) | O2—Cu1—N2—C18 | 0.0 (2) |
C12—C13—C14—C15 | −1.6 (4) | N1—Cu1—N2—C18 | 176.9 (2) |
C13—C14—C15—C19 | 2.1 (4) | O2—Cu1—N2—C19 | −178.42 (15) |
C13—C14—C15—C16 | −177.4 (3) | N1—Cu1—N2—C19 | −1.54 (15) |
C19—C15—C16—C17 | 0.1 (4) | O1—C1—O2—Cu1 | 8.4 (3) |
C14—C15—C16—C17 | 179.6 (3) | C2—C1—O2—Cu1 | −169.92 (12) |
C15—C16—C17—C18 | 0.4 (4) | O4i—Cu1—O2—C1 | −80.99 (13) |
C16—C17—C18—N2 | 0.0 (5) | N2—Cu1—O2—C1 | 102.08 (14) |
C16—C15—C19—N2 | −1.0 (3) | O5—C8—O4—Cu1ii | 0.6 (2) |
C14—C15—C19—N2 | 179.5 (2) | C6—C8—O4—Cu1ii | 179.91 (13) |
C16—C15—C19—C20 | 177.9 (2) |
Symmetry codes: (i) −x−1/2, y−1/2, −z+3/2; (ii) −x−1/2, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3B···O5iii | 0.82 | 1.86 | 2.677 (2) | 173 |
Symmetry code: (iii) x+1/2, −y+1/2, z+1/2. |
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