Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031514/br6170sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031514/br6170Isup2.hkl |
CCDC reference: 216374
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.037
- wR factor = 0.125
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.97 Deg. PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C14
Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.41 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
[Cu(C2F3O2)(C2H3O2)(C10H9N3)] | Z = 2 |
Mr = 406.81 | F(000) = 410 |
Triclinic, P1 | Dx = 1.716 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2533 (11) Å | Cell parameters from 2990 reflections |
b = 8.7907 (15) Å | θ = 2.0–25.0° |
c = 11.3643 (14) Å | µ = 1.45 mm−1 |
α = 87.199 (15)° | T = 293 K |
β = 84.592 (14)° | Block, black |
γ = 73.620 (11)° | 0.56 × 0.50 × 0.34 mm |
V = 787.3 (2) Å3 |
Enraf–Nonius TurboCAD-4 diffractometer | 2332 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.012 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
non–profiled ω/2θ scans | h = −9→0 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→10 |
Tmin = 0.456, Tmax = 0.612 | l = −13→13 |
2985 measured reflections | 3 standard reflections every 60 min |
2775 independent reflections | intensity decay: none |
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)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
2775 reflections | Δρmax = 0.61 e Å−3 |
239 parameters | Δρmin = −0.40 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.014 (3) |
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 | ||
Cu | 0.08831 (4) | 0.12749 (4) | 0.66054 (3) | 0.0454 (2) | |
F1 | 0.3557 (6) | 0.4085 (4) | 0.9629 (3) | 0.1261 (12) | |
F2 | 0.1474 (5) | 0.3206 (5) | 0.9823 (3) | 0.1369 (14) | |
F3 | 0.3755 (6) | 0.1732 (4) | 0.9214 (3) | 0.1342 (14) | |
O1 | 0.2450 (3) | −0.0781 (3) | 0.7132 (2) | 0.0589 (6) | |
O2 | 0.0431 (3) | 0.0627 (3) | 0.82814 (19) | 0.0571 (6) | |
O3 | 0.2590 (3) | 0.2685 (3) | 0.7143 (2) | 0.0583 (6) | |
O4 | 0.1937 (4) | 0.5188 (3) | 0.7713 (2) | 0.0826 (9) | |
N1 | 0.1539 (3) | 0.1155 (3) | 0.4916 (2) | 0.0439 (6) | |
N2 | −0.0701 (3) | 0.3345 (3) | 0.4376 (2) | 0.0504 (6) | |
H2B | −0.1117 | 0.3905 | 0.3777 | 0.076 (12)* | |
N3 | −0.1113 (3) | 0.3081 (3) | 0.6457 (2) | 0.0460 (6) | |
C1 | 0.2967 (4) | 0.0005 (4) | 0.4556 (3) | 0.0568 (8) | |
H1A | 0.3542 | −0.0679 | 0.5125 | 0.044 (8)* | |
C2 | 0.3587 (5) | −0.0194 (5) | 0.3408 (3) | 0.0654 (10) | |
H2A | 0.4571 | −0.0990 | 0.3199 | 0.075 (12)* | |
C3 | 0.2736 (5) | 0.0818 (5) | 0.2560 (3) | 0.0642 (9) | |
H3A | 0.3136 | 0.0701 | 0.1767 | 0.084 (13)* | |
C4 | 0.1302 (4) | 0.1983 (4) | 0.2887 (3) | 0.0562 (8) | |
H4A | 0.0718 | 0.2665 | 0.2320 | 0.051 (9)* | |
C5 | 0.0724 (4) | 0.2143 (4) | 0.4084 (3) | 0.0449 (7) | |
C6 | −0.1599 (4) | 0.3840 (3) | 0.5435 (3) | 0.0436 (6) | |
C7 | −0.3018 (4) | 0.5138 (4) | 0.5415 (3) | 0.0520 (7) | |
H7A | −0.3327 | 0.5651 | 0.4700 | 0.049 (9)* | |
C8 | −0.3961 (4) | 0.5671 (4) | 0.6440 (3) | 0.0578 (8) | |
H8A | −0.4915 | 0.6541 | 0.6434 | 0.059 (10)* | |
C9 | −0.3466 (5) | 0.4888 (5) | 0.7499 (3) | 0.0637 (9) | |
H9A | −0.4092 | 0.5218 | 0.8210 | 0.079 (13)* | |
C10 | −0.2062 (5) | 0.3641 (4) | 0.7474 (3) | 0.0615 (9) | |
H10A | −0.1728 | 0.3136 | 0.8186 | 0.062 (11)* | |
C11 | 0.1706 (4) | −0.0558 (4) | 0.8149 (3) | 0.0513 (7) | |
C12 | 0.2300 (6) | −0.1661 (5) | 0.9162 (3) | 0.0712 (11) | |
H12A | 0.1843 | −0.2551 | 0.9161 | 0.13 (2)* | |
H12B | 0.3515 | −0.2027 | 0.9089 | 0.15 (3)* | |
H12C | 0.1921 | −0.1109 | 0.9890 | 0.084 (13)* | |
C13 | 0.2405 (4) | 0.3735 (4) | 0.7860 (3) | 0.0476 (7) | |
C14 | 0.2836 (5) | 0.3196 (4) | 0.9131 (3) | 0.0627 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.0482 (3) | 0.0486 (3) | 0.0346 (3) | −0.00578 (17) | −0.00511 (16) | 0.00166 (16) |
F1 | 0.216 (4) | 0.127 (2) | 0.0733 (18) | −0.093 (2) | −0.078 (2) | 0.0247 (16) |
F2 | 0.134 (3) | 0.214 (4) | 0.0616 (17) | −0.060 (3) | 0.0148 (18) | 0.022 (2) |
F3 | 0.196 (4) | 0.0920 (19) | 0.086 (2) | 0.017 (2) | −0.058 (2) | 0.0163 (16) |
O1 | 0.0673 (15) | 0.0525 (13) | 0.0486 (13) | −0.0047 (11) | −0.0030 (11) | 0.0046 (10) |
O2 | 0.0623 (14) | 0.0589 (13) | 0.0421 (12) | −0.0061 (11) | −0.0015 (10) | 0.0057 (10) |
O3 | 0.0631 (14) | 0.0652 (14) | 0.0482 (13) | −0.0187 (11) | −0.0050 (11) | −0.0135 (11) |
O4 | 0.122 (2) | 0.0575 (15) | 0.0509 (15) | 0.0101 (15) | −0.0287 (15) | −0.0032 (12) |
N1 | 0.0423 (13) | 0.0514 (14) | 0.0373 (13) | −0.0105 (11) | −0.0055 (10) | −0.0062 (11) |
N2 | 0.0551 (15) | 0.0571 (15) | 0.0321 (13) | −0.0028 (12) | −0.0098 (11) | 0.0005 (11) |
N3 | 0.0455 (14) | 0.0522 (14) | 0.0372 (13) | −0.0081 (11) | −0.0050 (10) | −0.0008 (10) |
C1 | 0.0497 (18) | 0.066 (2) | 0.0480 (18) | −0.0033 (15) | −0.0080 (14) | −0.0048 (15) |
C2 | 0.057 (2) | 0.073 (2) | 0.056 (2) | −0.0010 (17) | −0.0006 (16) | −0.0157 (18) |
C3 | 0.067 (2) | 0.083 (2) | 0.0425 (18) | −0.0199 (19) | 0.0032 (16) | −0.0127 (17) |
C4 | 0.059 (2) | 0.071 (2) | 0.0364 (16) | −0.0143 (16) | −0.0074 (14) | 0.0000 (15) |
C5 | 0.0463 (16) | 0.0541 (16) | 0.0369 (15) | −0.0162 (13) | −0.0080 (12) | −0.0035 (13) |
C6 | 0.0454 (15) | 0.0511 (16) | 0.0372 (15) | −0.0161 (13) | −0.0096 (12) | −0.0031 (12) |
C7 | 0.0512 (18) | 0.0579 (18) | 0.0430 (17) | −0.0062 (14) | −0.0134 (14) | −0.0001 (14) |
C8 | 0.0479 (18) | 0.0638 (19) | 0.056 (2) | −0.0060 (15) | −0.0062 (15) | −0.0018 (15) |
C9 | 0.056 (2) | 0.075 (2) | 0.0490 (19) | −0.0013 (17) | 0.0011 (16) | −0.0075 (17) |
C10 | 0.062 (2) | 0.075 (2) | 0.0382 (17) | −0.0054 (17) | −0.0032 (15) | 0.0021 (15) |
C11 | 0.0601 (19) | 0.0496 (17) | 0.0439 (17) | −0.0143 (15) | −0.0080 (14) | 0.0025 (14) |
C12 | 0.096 (3) | 0.058 (2) | 0.051 (2) | −0.007 (2) | −0.013 (2) | 0.0098 (17) |
C13 | 0.0461 (16) | 0.0544 (18) | 0.0398 (16) | −0.0082 (13) | −0.0080 (12) | −0.0026 (13) |
C14 | 0.080 (2) | 0.063 (2) | 0.0457 (19) | −0.0189 (18) | −0.0149 (17) | 0.0054 (16) |
Cu—N1 | 1.945 (2) | C1—H1A | 0.9299 |
Cu—N3 | 1.953 (3) | C2—C3 | 1.381 (5) |
Cu—O2 | 1.993 (2) | C2—H2A | 0.9300 |
Cu—O1 | 2.005 (2) | C3—C4 | 1.363 (5) |
Cu—O3 | 2.262 (2) | C3—H3A | 0.9300 |
Cu—C11 | 2.338 (3) | C4—C5 | 1.398 (4) |
F1—C14 | 1.286 (5) | C4—H4A | 0.9300 |
F2—C14 | 1.308 (5) | C6—C7 | 1.387 (4) |
F3—C14 | 1.301 (5) | C7—C8 | 1.364 (5) |
O1—C11 | 1.254 (4) | C7—H7A | 0.9300 |
O2—C11 | 1.258 (4) | C8—C9 | 1.393 (5) |
O3—C13 | 1.229 (4) | C8—H8A | 0.9300 |
O4—C13 | 1.234 (4) | C9—C10 | 1.351 (5) |
N1—C5 | 1.345 (4) | C9—H9A | 0.9300 |
N1—C1 | 1.362 (4) | C10—H10A | 0.9300 |
N2—C5 | 1.368 (4) | C11—C12 | 1.494 (4) |
N2—C6 | 1.374 (4) | C12—H12A | 0.9600 |
N2—H2B | 0.8600 | C12—H12B | 0.9600 |
N3—C6 | 1.348 (4) | C12—H12C | 0.9601 |
N3—C10 | 1.363 (4) | C13—C14 | 1.539 (4) |
C1—C2 | 1.357 (5) | ||
N1—Cu—N3 | 94.58 (11) | N1—C5—N2 | 121.3 (3) |
N1—Cu—O2 | 161.08 (11) | N1—C5—C4 | 121.3 (3) |
N3—Cu—O2 | 99.61 (10) | N2—C5—C4 | 117.4 (3) |
N1—Cu—O1 | 98.99 (10) | N3—C6—N2 | 120.8 (3) |
N3—Cu—O1 | 162.51 (11) | N3—C6—C7 | 121.3 (3) |
O2—Cu—O1 | 64.90 (9) | N2—C6—C7 | 117.8 (3) |
N1—Cu—O3 | 99.66 (9) | C8—C7—C6 | 120.2 (3) |
N3—Cu—O3 | 96.25 (10) | C8—C7—H7A | 119.8 |
O2—Cu—O3 | 91.21 (10) | C6—C7—H7A | 120.0 |
O1—Cu—O3 | 92.31 (10) | C7—C8—C9 | 118.7 (3) |
N1—Cu—C11 | 131.08 (11) | C7—C8—H8A | 120.7 |
N3—Cu—C11 | 131.97 (11) | C9—C8—H8A | 120.6 |
O2—Cu—C11 | 32.55 (10) | C10—C9—C8 | 118.9 (3) |
O1—Cu—C11 | 32.43 (10) | C10—C9—H9A | 120.5 |
O3—Cu—C11 | 90.44 (10) | C8—C9—H9A | 120.5 |
C11—O1—Cu | 88.59 (19) | C9—C10—N3 | 123.3 (3) |
C11—O2—Cu | 89.01 (19) | C9—C10—H10A | 118.4 |
C13—O3—Cu | 133.6 (2) | N3—C10—H10A | 118.3 |
C5—N1—C1 | 117.8 (3) | O2—C11—O1 | 117.2 (3) |
C5—N1—Cu | 125.2 (2) | O2—C11—C12 | 121.3 (3) |
C1—N1—Cu | 117.0 (2) | O1—C11—C12 | 121.5 (3) |
C5—N2—C6 | 132.8 (3) | O2—C11—Cu | 58.44 (16) |
C5—N2—H2B | 113.6 | O1—C11—Cu | 58.99 (16) |
C6—N2—H2B | 113.6 | C12—C11—Cu | 176.1 (3) |
C6—N3—C10 | 117.6 (3) | C11—C12—H12A | 109.6 |
C6—N3—Cu | 125.2 (2) | C11—C12—H12B | 109.6 |
C10—N3—Cu | 117.2 (2) | H12A—C12—H12B | 109.5 |
N1—C1—C2 | 123.2 (3) | C11—C12—H12C | 109.3 |
N1—C1—H1A | 118.3 | H12A—C12—H12C | 109.5 |
C2—C1—H1A | 118.4 | H12B—C12—H12C | 109.5 |
C1—C2—C3 | 118.6 (3) | O4—C13—O3 | 129.4 (3) |
C1—C2—H2A | 120.6 | O4—C13—C14 | 113.9 (3) |
C3—C2—H2A | 120.8 | O3—C13—C14 | 116.7 (3) |
C4—C3—C2 | 119.8 (3) | F1—C14—F3 | 108.7 (4) |
C4—C3—H3A | 120.1 | F1—C14—F2 | 105.4 (4) |
C2—C3—H3A | 120.1 | F3—C14—F2 | 103.0 (4) |
C3—C4—C5 | 119.3 (3) | F1—C14—C13 | 113.8 (3) |
C3—C4—H4A | 120.3 | F3—C14—C13 | 113.5 (3) |
C5—C4—H4A | 120.5 | F2—C14—C13 | 111.5 (3) |