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The title compound, [Cu(C10H11ClNO)2], has been structurally characterized in the low-temperature phase (brown form). It adopts a stepped conformation and affords a square-planar trans-[CuN2O2] coordination geometry, in which the CuII ion lies on a center of symmetry. The Cu—N and Cu—O bond distances are 2.032 (3) and 1.891 (2) Å, respectively.
Supporting information
CCDC reference: 238661
Key indicators
- Single-crystal X-ray study
- T = 297 K
- R factor = 0.026
- wR factor = 0.111
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ?
PLAT156_ALERT_4_C Axial System Input Cell not Standard ........... ?
0 ALERT level A = In general: serious problem
0 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
0 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
Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Crystal data top
[Cu(C10H11ClNO)2] | Z = 1 |
Mr = 456.85 | F(000) = 235.0 |
Triclinic, P1 | Dx = 1.551 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 8.648 (4) Å | Cell parameters from 25 reflections |
b = 8.994 (9) Å | θ = 10.1–13.7° |
c = 7.294 (3) Å | µ = 1.41 mm−1 |
α = 97.98 (5)° | T = 297 K |
β = 107.00 (3)° | Prism, brown |
γ = 64.40 (5)° | 0.60 × 0.40 × 0.30 mm |
V = 489.2 (6) Å3 | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.026 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: psi scan (North et al., 1968) | h = −11→10 |
Tmin = 0.514, Tmax = 0.656 | k = −11→4 |
2525 measured reflections | l = −9→9 |
2251 independent reflections | 3 standard reflections every 150 reflections |
2012 reflections with I > 2σ(I) | intensity decay: 1.1% |
Refinement top
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.026 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.111 | (Δ/σ)max = 0.001 |
S = 0.97 | Δρmax = 0.34 e Å−3 |
2012 reflections | Δρmin = −0.40 e Å−3 |
124 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The
weighted R-factor (wR), goodness of fit (S) and
R-factor (gt) are based on F, with F set to zero for
negative F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 1.0000 | 0.0000 | 1.0000 | 0.0294 (1) | |
Cl1 | 1.18842 (7) | 0.65056 (6) | 0.77400 (8) | 0.0423 (2) | |
O1 | 1.1923 (2) | 0.0497 (2) | 1.0043 (2) | 0.0431 (3) | |
N1 | 0.8446 (2) | 0.1517 (2) | 0.7741 (2) | 0.0289 (3) | |
C1 | 1.1863 (2) | 0.1841 (2) | 0.9488 (3) | 0.0321 (4) | |
C2 | 1.3363 (2) | 0.2208 (3) | 1.0149 (3) | 0.0395 (4) | |
C3 | 1.3374 (3) | 0.3605 (3) | 0.9613 (3) | 0.0384 (4) | |
C4 | 1.1871 (2) | 0.4705 (2) | 0.8382 (3) | 0.0323 (4) | |
C5 | 1.0385 (2) | 0.4395 (2) | 0.7672 (3) | 0.0311 (3) | |
C6 | 1.0349 (2) | 0.2980 (2) | 0.8218 (2) | 0.0285 (3) | |
C7 | 0.8777 (2) | 0.2677 (2) | 0.7347 (2) | 0.0303 (3) | |
C8 | 0.6823 (2) | 0.1326 (2) | 0.6517 (3) | 0.0335 (4) | |
C9 | 0.5345 (3) | 0.2872 (3) | 0.5516 (3) | 0.0448 (5) | |
C10 | 0.7397 (3) | −0.0055 (3) | 0.5073 (4) | 0.0564 (6) | |
H1 | 1.4407 | 0.1451 | 1.0979 | 0.0453* | |
H2 | 1.4415 | 0.3823 | 1.0074 | 0.0447* | |
H3 | 0.9373 | 0.5155 | 0.6818 | 0.0358* | |
H4 | 0.7891 | 0.3435 | 0.6379 | 0.0349* | |
H5 | 0.6357 | 0.0970 | 0.7324 | 0.0401* | |
H6 | 0.4966 | 0.3707 | 0.6436 | 0.0534* | |
H7 | 0.5771 | 0.3248 | 0.4687 | 0.0534* | |
H8 | 0.4370 | 0.2634 | 0.4774 | 0.0534* | |
H9 | 0.6417 | −0.0273 | 0.4344 | 0.0652* | |
H10 | 0.7880 | 0.0254 | 0.4254 | 0.0652* | |
H11 | 0.8293 | −0.1032 | 0.5742 | 0.0652* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0271 (2) | 0.0320 (2) | 0.0300 (2) | −0.0132 (1) | 0.0022 (1) | 0.0112 (1) |
Cl1 | 0.0478 (3) | 0.0374 (3) | 0.0509 (3) | −0.0243 (2) | 0.0135 (2) | 0.0051 (2) |
O1 | 0.0303 (6) | 0.0461 (8) | 0.0545 (9) | −0.0171 (6) | −0.0009 (6) | 0.0270 (7) |
N1 | 0.0282 (7) | 0.0319 (7) | 0.0263 (7) | −0.0134 (6) | 0.0021 (5) | 0.0070 (5) |
C1 | 0.0312 (8) | 0.0377 (9) | 0.0288 (8) | −0.0148 (7) | 0.0056 (6) | 0.0080 (7) |
C2 | 0.0303 (8) | 0.049 (1) | 0.0382 (9) | −0.0180 (8) | −0.0023 (7) | 0.0151 (8) |
C3 | 0.0347 (9) | 0.048 (1) | 0.0388 (10) | −0.0246 (8) | 0.0036 (7) | 0.0057 (8) |
C4 | 0.0372 (9) | 0.0339 (9) | 0.0319 (8) | −0.0192 (7) | 0.0107 (7) | 0.0007 (7) |
C5 | 0.0327 (8) | 0.0320 (9) | 0.0292 (8) | −0.0141 (7) | 0.0046 (6) | 0.0066 (6) |
C6 | 0.0276 (7) | 0.0337 (8) | 0.0242 (7) | −0.0133 (6) | 0.0039 (6) | 0.0048 (6) |
C7 | 0.0304 (8) | 0.0334 (8) | 0.0264 (8) | −0.0139 (7) | 0.0015 (6) | 0.0086 (6) |
C8 | 0.0289 (8) | 0.0386 (9) | 0.0338 (9) | −0.0173 (7) | −0.0005 (7) | 0.0106 (7) |
C9 | 0.0292 (9) | 0.048 (1) | 0.051 (1) | −0.0145 (8) | −0.0014 (8) | 0.0149 (9) |
C10 | 0.046 (1) | 0.050 (1) | 0.057 (1) | −0.018 (1) | −0.002 (1) | −0.010 (1) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.891 (2) | C5—C6 | 1.400 (3) |
Cu1—N1 | 2.032 (3) | C5—H3 | 0.950 |
Cl1—C4 | 1.752 (2) | C6—C7 | 1.446 (3) |
O1—C1 | 1.303 (3) | C7—H4 | 0.957 |
N1—C7 | 1.282 (3) | C8—C9 | 1.517 (2) |
N1—C8 | 1.493 (3) | C8—C10 | 1.519 (3) |
C1—C2 | 1.408 (3) | C8—H5 | 0.956 |
C1—C6 | 1.420 (2) | C9—H6 | 0.948 |
C2—C3 | 1.372 (4) | C9—H7 | 0.953 |
C2—H1 | 0.953 | C9—H8 | 0.952 |
C3—C4 | 1.388 (2) | C10—H9 | 0.944 |
C3—H2 | 0.959 | C10—H10 | 0.949 |
C4—C5 | 1.371 (3) | C10—H11 | 0.959 |
| | | |
O1—Cu1—N1 | 90.70 (7) | C5—C6—C7 | 117.7 (1) |
O1—Cu1—N1i | 89.30 (7) | N1—C7—C6 | 127.1 (1) |
Cu1—O1—C1 | 128.0 (1) | N1—C7—H4 | 117.0 |
Cu1—N1—C7 | 122.3 (1) | C6—C7—H4 | 115.9 |
Cu1—N1—C8 | 119.6 (1) | N1—C8—C9 | 115.6 (2) |
C7—N1—C8 | 118.0 (1) | N1—C8—C10 | 107.8 (2) |
O1—C1—C2 | 119.6 (1) | N1—C8—H5 | 107.5 |
O1—C1—C6 | 123.4 (2) | C9—C8—C10 | 110.8 (2) |
C2—C1—C6 | 117.1 (2) | C9—C8—H5 | 107.6 |
C1—C2—C3 | 122.0 (2) | C10—C8—H5 | 107.2 |
C1—C2—H1 | 118.8 | C8—C9—H6 | 109.9 |
C3—C2—H1 | 119.2 | C8—C9—H7 | 109.3 |
C2—C3—C4 | 119.8 (2) | C8—C9—H8 | 109.7 |
C2—C3—H2 | 120.5 | H6—C9—H7 | 109.4 |
C4—C3—H2 | 119.8 | H6—C9—H8 | 109.5 |
Cl1—C4—C3 | 119.4 (2) | H7—C9—H8 | 109.0 |
Cl1—C4—C5 | 120.0 (1) | C8—C10—H9 | 110.1 |
C3—C4—C5 | 120.6 (2) | C8—C10—H10 | 109.4 |
C4—C5—C6 | 120.3 (1) | C8—C10—H11 | 109.3 |
C4—C5—H3 | 119.5 | H9—C10—H10 | 110.1 |
C6—C5—H3 | 120.2 | H9—C10—H11 | 109.2 |
C1—C6—C5 | 120.3 (2) | H10—C10—H11 | 108.8 |
C1—C6—C7 | 121.9 (2) | | |
| | | |
Cu1—O1—C1—C2 | 160.5 (1) | O1—C1—C6—C7 | −3.7 (3) |
Cu1—O1—C1—C6 | −20.0 (3) | N1—Cu1—O1—C1 | 27.9 (2) |
Cu1—O1i—C1i—C2i | −160.5 (1) | N1—Cu1—O1i—C1i | 152.1 (2) |
Cu1—O1i—C1i—C6i | 20.0 (3) | N1—C7—C6—C1 | 8.8 (3) |
Cu1—N1—C7—C6 | 8.4 (3) | N1—C7—C6—C5 | −175.4 (2) |
Cu1—N1—C8—C9 | 153.0 (2) | C1—C2—C3—C4 | 0.0 (3) |
Cu1—N1—C8—C10 | −82.4 (2) | C1—C6—C5—C4 | −1.0 (3) |
Cu1—N1i—C7i—C6i | −8.4 (3) | C2—C1—C6—C5 | 0.0 (3) |
Cu1—N1i—C8i—C9i | −153.0 (2) | C2—C1—C6—C7 | 175.8 (2) |
Cu1—N1i—C8i—C10i | 82.4 (2) | C2—C3—C4—C5 | −1.1 (3) |
Cl1—C4—C3—C2 | 178.8 (2) | C3—C2—C1—C6 | 0.5 (3) |
Cl1—C4—C5—C6 | −178.3 (1) | C3—C4—C5—C6 | 1.6 (3) |
O1—Cu1—N1—C7 | −21.5 (1) | C4—C5—C6—C7 | −177.0 (2) |
O1—Cu1—N1—C8 | 160.5 (1) | C6—C7—N1—C8 | −173.5 (2) |
O1—Cu1—N1i—C7i | −158.5 (1) | C7—N1—C8—C9 | −25.1 (2) |
O1—Cu1—N1i—C8i | 19.5 (1) | C7—N1—C8—C10 | 99.5 (2) |
O1—C1—C2—C3 | −180.0 (2) | C7—N1—C8—C10 | 99.5 (2) |
O1—C1—C6—C5 | −179.5 (2) | | |
Symmetry code: (i) −x+2, −y, −z+2. |
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