Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014357/na6340sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014357/na6340Isup2.hkl |
CCDC reference: 245148
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON ( Spek, 2003).
[Cu(C15H11ClN2O3)(C5H5N)] | Z = 2 |
Mr = 445.35 | F(000) = 454 |
Triclinic, P1 | Dx = 1.607 Mg m−3 |
a = 7.6672 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.3085 (7) Å | Cell parameters from 7701 reflections |
c = 14.6960 (12) Å | θ = 2.4–27.0° |
α = 97.960 (2)° | µ = 1.36 mm−1 |
β = 93.595 (2)° | T = 273 K |
γ = 95.405 (1)° | Block, dark blue |
V = 920.31 (13) Å3 | 0.41 × 0.36 × 0.24 mm |
Bruker SMART APEX CCD area-detector diffractometer | 3984 independent reflections |
Radiation source: fine-focus sealed tube | 3772 reflections with I > 2/s(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.0°, θmin = 2.4° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −10→10 |
Tmin = 0.592, Tmax = 0.721 | l = −18→18 |
10319 measured reflections |
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)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0446P)2 + 0.1871P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3984 reflections | Δρmax = 0.25 e Å−3 |
255 parameters | Δρmin = −0.23 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: 0.0119 (18) |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.75487 (2) | 0.52913 (2) | 0.090779 (11) | 0.03938 (9) | |
Cl1 | 0.75367 (8) | 0.34476 (8) | −0.49596 (3) | 0.07209 (16) | |
O1 | 0.78306 (15) | 0.44294 (14) | −0.03628 (8) | 0.0432 (2) | |
O2 | 0.75302 (16) | 0.65257 (15) | 0.20830 (8) | 0.0468 (3) | |
O3 | 0.76142 (18) | 0.75695 (17) | 0.38279 (8) | 0.0561 (3) | |
N1 | 0.61711 (18) | 0.65172 (16) | −0.06421 (9) | 0.0420 (3) | |
N2 | 0.63615 (17) | 0.68417 (16) | 0.03158 (9) | 0.0389 (3) | |
N3 | 0.85531 (17) | 0.34606 (16) | 0.14420 (9) | 0.0395 (3) | |
C1 | 0.6130 (2) | 0.55112 (19) | −0.25473 (11) | 0.0424 (3) | |
H1 | 0.5400 | 0.6292 | −0.2337 | 0.051* | |
C2 | 0.6247 (2) | 0.5098 (2) | −0.34804 (11) | 0.0470 (4) | |
H2 | 0.5592 | 0.5582 | −0.3901 | 0.056* | |
C3 | 0.7359 (2) | 0.3949 (2) | −0.37793 (11) | 0.0455 (4) | |
C4 | 0.8321 (2) | 0.3196 (2) | −0.31736 (12) | 0.0483 (4) | |
H4 | 0.9061 | 0.2426 | −0.3388 | 0.058* | |
C5 | 0.8168 (2) | 0.3600 (2) | −0.22447 (11) | 0.0437 (3) | |
H5 | 0.8795 | 0.3081 | −0.1829 | 0.052* | |
C6 | 0.70917 (19) | 0.47720 (18) | −0.19159 (10) | 0.0369 (3) | |
C7 | 0.70261 (19) | 0.52495 (18) | −0.09123 (10) | 0.0374 (3) | |
C8 | 0.5635 (2) | 0.80707 (19) | 0.07073 (11) | 0.0421 (3) | |
H8 | 0.5017 | 0.8666 | 0.0329 | 0.051* | |
C9 | 0.5712 (2) | 0.85798 (18) | 0.16786 (11) | 0.0403 (3) | |
C10 | 0.6657 (2) | 0.77813 (18) | 0.23097 (11) | 0.0392 (3) | |
C11 | 0.6641 (2) | 0.83791 (19) | 0.32630 (11) | 0.0427 (3) | |
C12 | 0.5708 (2) | 0.9662 (2) | 0.35613 (12) | 0.0494 (4) | |
H12 | 0.5698 | 1.0023 | 0.4189 | 0.059* | |
C13 | 0.4776 (3) | 1.0427 (2) | 0.29249 (13) | 0.0556 (4) | |
H13 | 0.4140 | 1.1288 | 0.3130 | 0.067* | |
C14 | 0.4796 (2) | 0.9914 (2) | 0.20069 (13) | 0.0493 (4) | |
H14 | 0.4198 | 1.0449 | 0.1588 | 0.059* | |
C15 | 0.7647 (3) | 0.8069 (3) | 0.47861 (13) | 0.0702 (6) | |
H15A | 0.8093 | 0.9202 | 0.4928 | 0.105* | |
H15B | 0.8393 | 0.7425 | 0.5102 | 0.105* | |
H15C | 0.6478 | 0.7921 | 0.4981 | 0.105* | |
C16 | 0.9210 (3) | 0.2269 (2) | 0.09047 (12) | 0.0523 (4) | |
H16 | 0.9181 | 0.2299 | 0.0274 | 0.063* | |
C17 | 0.9926 (3) | 0.1005 (3) | 0.12474 (14) | 0.0663 (6) | |
H17 | 1.0380 | 0.0201 | 0.0854 | 0.080* | |
C18 | 0.9966 (3) | 0.0935 (2) | 0.21774 (14) | 0.0580 (5) | |
H18 | 1.0428 | 0.0079 | 0.2423 | 0.070* | |
C19 | 0.9308 (3) | 0.2154 (2) | 0.27300 (12) | 0.0529 (4) | |
H19 | 0.9325 | 0.2145 | 0.3363 | 0.064* | |
C20 | 0.8621 (2) | 0.3397 (2) | 0.23469 (11) | 0.0462 (4) | |
H20 | 0.8186 | 0.4226 | 0.2732 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.04743 (13) | 0.03901 (12) | 0.03373 (12) | 0.01612 (8) | 0.00137 (8) | 0.00537 (8) |
Cl1 | 0.0962 (4) | 0.0831 (4) | 0.0374 (2) | 0.0299 (3) | 0.0042 (2) | −0.0034 (2) |
O1 | 0.0505 (6) | 0.0463 (6) | 0.0358 (5) | 0.0189 (5) | 0.0018 (4) | 0.0082 (4) |
O2 | 0.0540 (7) | 0.0494 (7) | 0.0387 (6) | 0.0254 (5) | −0.0003 (5) | 0.0005 (5) |
O3 | 0.0653 (8) | 0.0671 (8) | 0.0389 (6) | 0.0290 (6) | 0.0027 (5) | 0.0032 (5) |
N1 | 0.0511 (7) | 0.0416 (7) | 0.0362 (6) | 0.0136 (6) | 0.0043 (5) | 0.0094 (5) |
N2 | 0.0446 (7) | 0.0373 (6) | 0.0363 (6) | 0.0092 (5) | 0.0031 (5) | 0.0078 (5) |
N3 | 0.0438 (7) | 0.0385 (6) | 0.0375 (6) | 0.0113 (5) | 0.0011 (5) | 0.0059 (5) |
C1 | 0.0498 (8) | 0.0390 (8) | 0.0412 (8) | 0.0134 (6) | 0.0040 (6) | 0.0089 (6) |
C2 | 0.0578 (10) | 0.0455 (9) | 0.0397 (8) | 0.0137 (7) | −0.0008 (7) | 0.0097 (7) |
C3 | 0.0538 (9) | 0.0455 (8) | 0.0361 (8) | 0.0057 (7) | 0.0034 (6) | 0.0017 (6) |
C4 | 0.0492 (9) | 0.0484 (9) | 0.0482 (9) | 0.0153 (7) | 0.0051 (7) | 0.0019 (7) |
C5 | 0.0435 (8) | 0.0457 (8) | 0.0435 (8) | 0.0133 (6) | 0.0006 (6) | 0.0076 (7) |
C6 | 0.0374 (7) | 0.0360 (7) | 0.0383 (7) | 0.0046 (6) | 0.0027 (6) | 0.0084 (6) |
C7 | 0.0377 (7) | 0.0385 (7) | 0.0375 (7) | 0.0057 (6) | 0.0030 (5) | 0.0090 (6) |
C8 | 0.0478 (8) | 0.0357 (7) | 0.0459 (8) | 0.0115 (6) | 0.0042 (6) | 0.0115 (6) |
C9 | 0.0454 (8) | 0.0314 (7) | 0.0456 (8) | 0.0084 (6) | 0.0072 (6) | 0.0068 (6) |
C10 | 0.0399 (7) | 0.0352 (7) | 0.0431 (8) | 0.0078 (6) | 0.0055 (6) | 0.0041 (6) |
C11 | 0.0464 (8) | 0.0397 (8) | 0.0428 (8) | 0.0078 (6) | 0.0062 (6) | 0.0047 (6) |
C12 | 0.0644 (10) | 0.0401 (8) | 0.0455 (9) | 0.0119 (7) | 0.0154 (7) | 0.0028 (7) |
C13 | 0.0754 (12) | 0.0368 (8) | 0.0595 (11) | 0.0223 (8) | 0.0189 (9) | 0.0071 (7) |
C14 | 0.0623 (10) | 0.0363 (8) | 0.0536 (10) | 0.0188 (7) | 0.0096 (8) | 0.0102 (7) |
C15 | 0.0889 (15) | 0.0834 (15) | 0.0406 (10) | 0.0308 (12) | 0.0039 (9) | 0.0027 (9) |
C16 | 0.0717 (11) | 0.0489 (9) | 0.0387 (8) | 0.0238 (8) | 0.0014 (7) | 0.0040 (7) |
C17 | 0.0964 (16) | 0.0528 (11) | 0.0540 (11) | 0.0376 (11) | 0.0032 (10) | 0.0033 (9) |
C18 | 0.0706 (12) | 0.0496 (10) | 0.0587 (11) | 0.0214 (9) | −0.0016 (9) | 0.0180 (8) |
C19 | 0.0623 (11) | 0.0604 (10) | 0.0409 (9) | 0.0154 (8) | 0.0031 (7) | 0.0186 (8) |
C20 | 0.0522 (9) | 0.0491 (9) | 0.0404 (8) | 0.0158 (7) | 0.0067 (7) | 0.0083 (7) |
Cu1—O2 | 1.8842 (11) | C6—C7 | 1.479 (2) |
Cu1—N2 | 1.9174 (13) | C8—C9 | 1.427 (2) |
Cu1—O1 | 1.9380 (11) | C8—H8 | 0.9300 |
Cu1—N3 | 1.9996 (13) | C9—C14 | 1.412 (2) |
Cl1—C3 | 1.7439 (17) | C9—C10 | 1.415 (2) |
O1—C7 | 1.2907 (18) | C10—C11 | 1.421 (2) |
O2—C10 | 1.3080 (18) | C11—C12 | 1.376 (2) |
O3—C11 | 1.367 (2) | C12—C13 | 1.398 (3) |
O3—C15 | 1.410 (2) | C12—H12 | 0.9300 |
N1—C7 | 1.320 (2) | C13—C14 | 1.359 (3) |
N1—N2 | 1.3920 (18) | C13—H13 | 0.9300 |
N2—C8 | 1.292 (2) | C14—H14 | 0.9300 |
N3—C16 | 1.336 (2) | C15—H15A | 0.9600 |
N3—C20 | 1.336 (2) | C15—H15B | 0.9600 |
C1—C2 | 1.377 (2) | C15—H15C | 0.9600 |
C1—C6 | 1.393 (2) | C16—C17 | 1.370 (3) |
C1—H1 | 0.9300 | C16—H16 | 0.9300 |
C2—C3 | 1.384 (2) | C17—C18 | 1.375 (3) |
C2—H2 | 0.9300 | C17—H17 | 0.9300 |
C3—C4 | 1.374 (2) | C18—C19 | 1.364 (3) |
C4—C5 | 1.375 (2) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | C19—C20 | 1.374 (2) |
C5—C6 | 1.391 (2) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—H20 | 0.9300 |
O2—Cu1—N2 | 92.63 (5) | C14—C9—C10 | 119.86 (15) |
O2—Cu1—O1 | 168.10 (5) | C14—C9—C8 | 118.17 (15) |
N2—Cu1—O1 | 81.18 (5) | C10—C9—C8 | 121.97 (14) |
O2—Cu1—N3 | 91.85 (5) | O2—C10—C9 | 124.98 (14) |
N2—Cu1—N3 | 172.75 (5) | O2—C10—C11 | 117.53 (14) |
O1—Cu1—N3 | 95.38 (5) | C9—C10—C11 | 117.49 (14) |
C7—O1—Cu1 | 110.25 (9) | O3—C11—C12 | 124.73 (15) |
C10—O2—Cu1 | 127.40 (10) | O3—C11—C10 | 114.06 (14) |
C11—O3—C15 | 117.73 (14) | C12—C11—C10 | 121.20 (15) |
C7—N1—N2 | 108.51 (12) | C11—C12—C13 | 120.27 (16) |
C8—N2—N1 | 117.40 (13) | C11—C12—H12 | 119.9 |
C8—N2—Cu1 | 127.27 (11) | C13—C12—H12 | 119.9 |
N1—N2—Cu1 | 115.17 (10) | C14—C13—C12 | 120.15 (16) |
C16—N3—C20 | 117.62 (14) | C14—C13—H13 | 119.9 |
C16—N3—Cu1 | 120.92 (11) | C12—C13—H13 | 119.9 |
C20—N3—Cu1 | 121.46 (11) | C13—C14—C9 | 120.99 (16) |
C2—C1—C6 | 120.74 (15) | C13—C14—H14 | 119.5 |
C2—C1—H1 | 119.6 | C9—C14—H14 | 119.5 |
C6—C1—H1 | 119.6 | O3—C15—H15A | 109.5 |
C1—C2—C3 | 118.71 (15) | O3—C15—H15B | 109.5 |
C1—C2—H2 | 120.6 | H15A—C15—H15B | 109.5 |
C3—C2—H2 | 120.6 | O3—C15—H15C | 109.5 |
C4—C3—C2 | 121.89 (15) | H15A—C15—H15C | 109.5 |
C4—C3—Cl1 | 119.30 (13) | H15B—C15—H15C | 109.5 |
C2—C3—Cl1 | 118.81 (13) | N3—C16—C17 | 122.54 (17) |
C3—C4—C5 | 118.75 (15) | N3—C16—H16 | 118.7 |
C3—C4—H4 | 120.6 | C17—C16—H16 | 118.7 |
C5—C4—H4 | 120.6 | C16—C17—C18 | 119.50 (18) |
C4—C5—C6 | 121.11 (15) | C16—C17—H17 | 120.3 |
C4—C5—H5 | 119.4 | C18—C17—H17 | 120.3 |
C6—C5—H5 | 119.4 | C19—C18—C17 | 118.20 (17) |
C5—C6—C1 | 118.77 (15) | C19—C18—H18 | 120.9 |
C5—C6—C7 | 120.01 (14) | C17—C18—H18 | 120.9 |
C1—C6—C7 | 121.19 (14) | C18—C19—C20 | 119.62 (16) |
O1—C7—N1 | 124.57 (13) | C18—C19—H19 | 120.2 |
O1—C7—C6 | 118.26 (13) | C20—C19—H19 | 120.2 |
N1—C7—C6 | 117.15 (13) | N3—C20—C19 | 122.51 (16) |
N2—C8—C9 | 124.67 (14) | N3—C20—H20 | 118.7 |
N2—C8—H8 | 117.7 | C19—C20—H20 | 118.7 |
C9—C8—H8 | 117.7 | ||
O2—Cu1—O1—C7 | −62.8 (3) | C5—C6—C7—O1 | −7.5 (2) |
N2—Cu1—O1—C7 | −3.55 (10) | C1—C6—C7—O1 | 174.40 (14) |
N3—Cu1—O1—C7 | 170.02 (11) | C5—C6—C7—N1 | 171.07 (15) |
N2—Cu1—O2—C10 | 11.17 (14) | C1—C6—C7—N1 | −7.0 (2) |
O1—Cu1—O2—C10 | 69.4 (3) | N1—N2—C8—C9 | −179.53 (14) |
N3—Cu1—O2—C10 | −163.14 (14) | Cu1—N2—C8—C9 | 5.4 (2) |
C7—N1—N2—C8 | 178.74 (14) | N2—C8—C9—C14 | −177.74 (16) |
C7—N1—N2—Cu1 | −5.57 (16) | N2—C8—C9—C10 | 1.7 (3) |
O2—Cu1—N2—C8 | −9.85 (15) | Cu1—O2—C10—C9 | −8.2 (2) |
O1—Cu1—N2—C8 | −179.62 (15) | Cu1—O2—C10—C11 | 171.13 (11) |
N3—Cu1—N2—C8 | 118.3 (4) | C14—C9—C10—O2 | 179.12 (15) |
O2—Cu1—N2—N1 | 174.96 (10) | C8—C9—C10—O2 | −0.3 (2) |
O1—Cu1—N2—N1 | 5.18 (10) | C14—C9—C10—C11 | −0.2 (2) |
N3—Cu1—N2—N1 | −56.9 (4) | C8—C9—C10—C11 | −179.63 (14) |
O2—Cu1—N3—C16 | −166.73 (14) | C15—O3—C11—C12 | 0.9 (3) |
N2—Cu1—N3—C16 | 65.1 (5) | C15—O3—C11—C10 | −179.04 (17) |
O1—Cu1—N3—C16 | 3.80 (14) | O2—C10—C11—O3 | 2.0 (2) |
O2—Cu1—N3—C20 | 12.09 (13) | C9—C10—C11—O3 | −178.62 (14) |
N2—Cu1—N3—C20 | −116.1 (4) | O2—C10—C11—C12 | −177.93 (16) |
O1—Cu1—N3—C20 | −177.38 (13) | C9—C10—C11—C12 | 1.4 (2) |
C6—C1—C2—C3 | −0.9 (3) | O3—C11—C12—C13 | 178.93 (17) |
C1—C2—C3—C4 | 1.0 (3) | C10—C11—C12—C13 | −1.1 (3) |
C1—C2—C3—Cl1 | −179.00 (13) | C11—C12—C13—C14 | −0.5 (3) |
C2—C3—C4—C5 | 0.0 (3) | C12—C13—C14—C9 | 1.8 (3) |
Cl1—C3—C4—C5 | −179.94 (13) | C10—C9—C14—C13 | −1.4 (3) |
C3—C4—C5—C6 | −1.3 (3) | C8—C9—C14—C13 | 178.06 (17) |
C4—C5—C6—C1 | 1.5 (2) | C20—N3—C16—C17 | 0.4 (3) |
C4—C5—C6—C7 | −176.64 (14) | Cu1—N3—C16—C17 | 179.30 (17) |
C2—C1—C6—C5 | −0.4 (2) | N3—C16—C17—C18 | 0.6 (4) |
C2—C1—C6—C7 | 177.72 (14) | C16—C17—C18—C19 | −1.0 (3) |
Cu1—O1—C7—N1 | 1.48 (19) | C17—C18—C19—C20 | 0.5 (3) |
Cu1—O1—C7—C6 | 179.98 (10) | C16—N3—C20—C19 | −1.0 (3) |
N2—N1—C7—O1 | 2.6 (2) | Cu1—N3—C20—C19 | −179.84 (14) |
N2—N1—C7—C6 | −175.88 (12) | C18—C19—C20—N3 | 0.5 (3) |