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
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.002 Å
- R factor = 0.026
- wR factor = 0.076
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1 .. 5.41 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - N2 .. 5.71 su PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 11 N3 -CU1 -N2 -C8 118.30 0.40 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14 N3 -CU1 -N2 -N1 -56.90 0.40 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 16 N2 -CU1 -N3 -C16 65.10 0.50 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 19 N2 -CU1 -N3 -C20 -116.10 0.40 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 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 0 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion
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) |
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