Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060163/ci2510sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060163/ci2510Isup2.hkl |
CCDC reference: 638052
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.096
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - Cl1_a .. 5.93 su
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of N3 ..... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
5-Nitrosalicylaldehyde (0.1 mmol, 16.5 mg), N-isopropylethane-1,2-diamine (0.1 mmol, 10.2 mg), and copper chloride dihydrate (0.1 mmol, 17.0 mg) were dissolved in a methanol solution (10 ml). The mixture was stirred at room temperature for 30 min, giving a clear blue solution. Crystals of the title compound were formed by slow evaporation of the solvent over a week at room temperature.
Atom H3A was located from a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1) Å, and with the Uiso(H) value fixed at 0.08 Å2. The remaining H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C–H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
[Cu(C12H16N3O3)Cl] | F(000) = 716 |
Mr = 349.27 | Dx = 1.643 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3124 reflections |
a = 9.762 (1) Å | θ = 2.2–26.0° |
b = 6.415 (1) Å | µ = 1.75 mm−1 |
c = 22.611 (3) Å | T = 298 K |
β = 94.353 (2)° | Block, blue |
V = 1411.9 (3) Å3 | 0.33 × 0.29 × 0.27 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3196 independent reflections |
Radiation source: fine-focus sealed tube | 2607 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.597, Tmax = 0.650 | k = −8→8 |
11191 measured reflections | l = −28→29 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0355P)2 + 1.0385P] where P = (Fo2 + 2Fc2)/3 |
3196 reflections | (Δ/σ)max = 0.001 |
186 parameters | Δρmax = 0.47 e Å−3 |
1 restraint | Δρmin = −0.50 e Å−3 |
[Cu(C12H16N3O3)Cl] | V = 1411.9 (3) Å3 |
Mr = 349.27 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.762 (1) Å | µ = 1.75 mm−1 |
b = 6.415 (1) Å | T = 298 K |
c = 22.611 (3) Å | 0.33 × 0.29 × 0.27 mm |
β = 94.353 (2)° |
Bruker SMART CCD area-detector diffractometer | 3196 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2607 reflections with I > 2σ(I) |
Tmin = 0.597, Tmax = 0.650 | Rint = 0.045 |
11191 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 1 restraint |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.47 e Å−3 |
3196 reflections | Δρmin = −0.50 e Å−3 |
186 parameters |
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 | 0.76386 (4) | 0.83895 (5) | 0.181248 (15) | 0.02930 (12) | |
Cl1 | 0.87605 (8) | 1.08051 (11) | 0.24016 (3) | 0.03700 (19) | |
O1 | 0.1740 (3) | 0.9670 (5) | −0.04462 (13) | 0.0726 (9) | |
O2 | 0.1089 (3) | 1.2464 (5) | −0.00250 (13) | 0.0774 (9) | |
O3 | 0.6076 (2) | 1.0252 (3) | 0.17348 (9) | 0.0350 (5) | |
N1 | 0.1850 (3) | 1.0962 (5) | −0.00511 (14) | 0.0507 (7) | |
N2 | 0.6771 (3) | 0.6547 (4) | 0.11980 (11) | 0.0323 (5) | |
N3 | 0.9188 (2) | 0.6230 (4) | 0.18510 (11) | 0.0303 (5) | |
C1 | 0.4874 (3) | 0.8788 (4) | 0.08619 (13) | 0.0315 (6) | |
C2 | 0.5112 (3) | 1.0351 (4) | 0.13091 (13) | 0.0305 (6) | |
C3 | 0.4235 (3) | 1.2127 (5) | 0.12726 (15) | 0.0382 (7) | |
H3 | 0.4372 | 1.3183 | 0.1553 | 0.046* | |
C4 | 0.3191 (3) | 1.2319 (5) | 0.08343 (15) | 0.0415 (8) | |
H4 | 0.2629 | 1.3490 | 0.0821 | 0.050* | |
C5 | 0.2974 (3) | 1.0762 (5) | 0.04096 (14) | 0.0388 (7) | |
C6 | 0.3792 (3) | 0.9025 (5) | 0.04230 (14) | 0.0365 (7) | |
H6 | 0.3627 | 0.7991 | 0.0138 | 0.044* | |
C7 | 0.5695 (3) | 0.6920 (4) | 0.08538 (13) | 0.0328 (7) | |
H7 | 0.5422 | 0.5905 | 0.0576 | 0.039* | |
C8 | 0.7463 (3) | 0.4534 (4) | 0.11834 (15) | 0.0401 (8) | |
H8A | 0.7286 | 0.3895 | 0.0796 | 0.048* | |
H8B | 0.7124 | 0.3609 | 0.1479 | 0.048* | |
C9 | 0.8987 (3) | 0.4889 (5) | 0.13117 (14) | 0.0370 (7) | |
H9A | 0.9455 | 0.3567 | 0.1380 | 0.044* | |
H9B | 0.9363 | 0.5571 | 0.0977 | 0.044* | |
C10 | 1.0653 (3) | 0.6924 (5) | 0.19822 (14) | 0.0347 (7) | |
H10 | 1.0672 | 0.7827 | 0.2332 | 0.042* | |
C11 | 1.1140 (4) | 0.8217 (6) | 0.14826 (17) | 0.0536 (9) | |
H11A | 1.1254 | 0.7339 | 0.1146 | 0.080* | |
H11B | 1.2003 | 0.8856 | 0.1608 | 0.080* | |
H11C | 1.0474 | 0.9279 | 0.1376 | 0.080* | |
C12 | 1.1584 (4) | 0.5073 (6) | 0.21439 (17) | 0.0523 (9) | |
H12A | 1.1618 | 0.4174 | 0.1806 | 0.078* | |
H12B | 1.1229 | 0.4314 | 0.2465 | 0.078* | |
H12C | 1.2492 | 0.5563 | 0.2263 | 0.078* | |
H3A | 0.893 (4) | 0.546 (6) | 0.2159 (12) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0326 (2) | 0.02052 (18) | 0.0340 (2) | 0.00192 (14) | −0.00242 (14) | −0.00460 (14) |
Cl1 | 0.0400 (4) | 0.0272 (4) | 0.0427 (4) | −0.0004 (3) | −0.0037 (3) | −0.0090 (3) |
O1 | 0.071 (2) | 0.074 (2) | 0.0672 (19) | 0.0107 (16) | −0.0334 (15) | −0.0090 (16) |
O2 | 0.0700 (19) | 0.092 (2) | 0.0670 (19) | 0.0411 (18) | −0.0155 (15) | 0.0043 (17) |
O3 | 0.0360 (11) | 0.0289 (11) | 0.0385 (12) | 0.0066 (9) | −0.0067 (9) | −0.0082 (9) |
N1 | 0.0459 (18) | 0.0576 (19) | 0.0476 (18) | 0.0078 (15) | −0.0037 (14) | 0.0140 (16) |
N2 | 0.0373 (14) | 0.0217 (12) | 0.0370 (14) | 0.0000 (10) | −0.0036 (11) | −0.0020 (10) |
N3 | 0.0318 (13) | 0.0247 (12) | 0.0343 (14) | −0.0002 (10) | 0.0011 (10) | −0.0004 (10) |
C1 | 0.0332 (16) | 0.0267 (15) | 0.0341 (16) | −0.0016 (12) | −0.0004 (12) | 0.0028 (12) |
C2 | 0.0302 (15) | 0.0251 (14) | 0.0363 (16) | 0.0003 (11) | 0.0040 (12) | 0.0040 (12) |
C3 | 0.0424 (18) | 0.0287 (16) | 0.0432 (18) | 0.0053 (13) | 0.0016 (14) | −0.0010 (13) |
C4 | 0.0407 (18) | 0.0356 (17) | 0.0485 (19) | 0.0125 (14) | 0.0055 (15) | 0.0114 (15) |
C5 | 0.0348 (17) | 0.0464 (19) | 0.0349 (17) | 0.0031 (14) | −0.0004 (13) | 0.0121 (15) |
C6 | 0.0397 (17) | 0.0340 (16) | 0.0351 (17) | −0.0017 (13) | −0.0014 (13) | 0.0002 (13) |
C7 | 0.0420 (17) | 0.0235 (14) | 0.0319 (15) | −0.0022 (12) | −0.0030 (13) | −0.0046 (12) |
C8 | 0.050 (2) | 0.0201 (15) | 0.0480 (19) | 0.0028 (13) | −0.0091 (15) | −0.0089 (13) |
C9 | 0.0436 (18) | 0.0237 (15) | 0.0429 (18) | 0.0070 (13) | −0.0018 (14) | −0.0083 (13) |
C10 | 0.0320 (16) | 0.0322 (16) | 0.0393 (17) | 0.0009 (12) | −0.0020 (13) | −0.0027 (13) |
C11 | 0.044 (2) | 0.058 (2) | 0.059 (2) | −0.0113 (17) | 0.0042 (17) | 0.0095 (19) |
C12 | 0.042 (2) | 0.049 (2) | 0.064 (2) | 0.0144 (16) | −0.0056 (17) | −0.0030 (18) |
Cu1—O3 | 1.935 (2) | C4—C5 | 1.390 (5) |
Cu1—N2 | 1.966 (3) | C4—H4 | 0.93 |
Cu1—N3 | 2.048 (3) | C5—C6 | 1.370 (4) |
Cu1—Cl1 | 2.2703 (8) | C6—H6 | 0.93 |
Cu1—Cl1i | 2.8531 (9) | C7—H7 | 0.93 |
O1—N1 | 1.217 (4) | C8—C9 | 1.511 (4) |
O2—N1 | 1.221 (4) | C8—H8A | 0.97 |
O3—C2 | 1.296 (3) | C8—H8B | 0.97 |
N1—C5 | 1.460 (4) | C9—H9A | 0.97 |
N2—C7 | 1.281 (4) | C9—H9B | 0.97 |
N2—C8 | 1.459 (4) | C10—C11 | 1.507 (5) |
N3—C9 | 1.493 (4) | C10—C12 | 1.523 (4) |
N3—C10 | 1.506 (4) | C10—H10 | 0.98 |
N3—H3A | 0.91 (3) | C11—H11A | 0.96 |
C1—C6 | 1.402 (4) | C11—H11B | 0.96 |
C1—C2 | 1.431 (4) | C11—H11C | 0.96 |
C1—C7 | 1.443 (4) | C12—H12A | 0.96 |
C2—C3 | 1.424 (4) | C12—H12B | 0.96 |
C3—C4 | 1.372 (4) | C12—H12C | 0.96 |
C3—H3 | 0.93 | ||
O3—Cu1—N2 | 90.74 (10) | C4—C5—N1 | 119.8 (3) |
O3—Cu1—N3 | 174.91 (9) | C5—C6—C1 | 120.7 (3) |
N2—Cu1—N3 | 84.29 (11) | C5—C6—H6 | 119.7 |
O3—Cu1—Cl1 | 88.48 (8) | C1—C6—H6 | 119.7 |
N2—Cu1—Cl1 | 171.01 (8) | N2—C7—C1 | 125.3 (3) |
N3—Cu1—Cl1 | 96.60 (9) | N2—C7—H7 | 117.3 |
O3—Cu1—Cl1i | 90.23 (7) | C1—C7—H7 | 117.3 |
N2—Cu1—Cl1i | 83.67 (8) | N2—C8—C9 | 108.3 (2) |
N3—Cu1—Cl1i | 88.13 (7) | N2—C8—H8A | 110.0 |
Cl1—Cu1—Cl1i | 105.28 (2) | C9—C8—H8A | 110.0 |
C2—O3—Cu1 | 128.38 (18) | N2—C8—H8B | 110.0 |
O1—N1—O2 | 123.6 (3) | C9—C8—H8B | 110.0 |
O1—N1—C5 | 118.9 (3) | H8A—C8—H8B | 108.4 |
O2—N1—C5 | 117.5 (3) | N3—C9—C8 | 108.0 (2) |
C7—N2—C8 | 120.8 (2) | N3—C9—H9A | 110.1 |
C7—N2—Cu1 | 127.3 (2) | C8—C9—H9A | 110.1 |
C8—N2—Cu1 | 111.87 (19) | N3—C9—H9B | 110.1 |
C9—N3—C10 | 113.3 (2) | C8—C9—H9B | 110.1 |
C9—N3—Cu1 | 107.72 (18) | H9A—C9—H9B | 108.4 |
C10—N3—Cu1 | 119.73 (18) | N3—C10—C11 | 111.3 (3) |
C9—N3—H3A | 107 (3) | N3—C10—C12 | 110.9 (3) |
C10—N3—H3A | 109 (3) | C11—C10—C12 | 113.1 (3) |
Cu1—N3—H3A | 99 (3) | N3—C10—H10 | 107.0 |
C6—C1—C2 | 119.8 (3) | C11—C10—H10 | 107.0 |
C6—C1—C7 | 118.1 (3) | C12—C10—H10 | 107.0 |
C2—C1—C7 | 122.0 (3) | C10—C11—H11A | 109.5 |
O3—C2—C3 | 118.8 (3) | C10—C11—H11B | 109.5 |
O3—C2—C1 | 124.1 (3) | H11A—C11—H11B | 109.5 |
C3—C2—C1 | 117.1 (3) | C10—C11—H11C | 109.5 |
C4—C3—C2 | 121.6 (3) | H11A—C11—H11C | 109.5 |
C4—C3—H3 | 119.2 | H11B—C11—H11C | 109.5 |
C2—C3—H3 | 119.2 | C10—C12—H12A | 109.5 |
C3—C4—C5 | 120.1 (3) | C10—C12—H12B | 109.5 |
C3—C4—H4 | 120.0 | H12A—C12—H12B | 109.5 |
C5—C4—H4 | 120.0 | C10—C12—H12C | 109.5 |
C6—C5—C4 | 120.7 (3) | H12A—C12—H12C | 109.5 |
C6—C5—N1 | 119.5 (3) | H12B—C12—H12C | 109.5 |
Symmetry code: (i) −x+3/2, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O3i | 0.91 (3) | 2.51 (3) | 3.288 (4) | 145 (3) |
C8—H8B···O3ii | 0.97 | 2.47 | 3.345 (3) | 150 |
C9—H9B···O2iii | 0.97 | 2.50 | 3.365 (4) | 148 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C12H16N3O3)Cl] |
Mr | 349.27 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 9.762 (1), 6.415 (1), 22.611 (3) |
β (°) | 94.353 (2) |
V (Å3) | 1411.9 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.75 |
Crystal size (mm) | 0.33 × 0.29 × 0.27 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.597, 0.650 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11191, 3196, 2607 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.096, 1.06 |
No. of reflections | 3196 |
No. of parameters | 186 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.47, −0.50 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1997), SHELXL97.
Cu1—O3 | 1.935 (2) | Cu1—Cl1 | 2.2703 (8) |
Cu1—N2 | 1.966 (3) | Cu1—Cl1i | 2.8531 (9) |
Cu1—N3 | 2.048 (3) | ||
O3—Cu1—N2 | 90.74 (10) | N3—Cu1—Cl1 | 96.60 (9) |
O3—Cu1—N3 | 174.91 (9) | O3—Cu1—Cl1i | 90.23 (7) |
N2—Cu1—N3 | 84.29 (11) | N2—Cu1—Cl1i | 83.67 (8) |
O3—Cu1—Cl1 | 88.48 (8) | N3—Cu1—Cl1i | 88.13 (7) |
N2—Cu1—Cl1 | 171.01 (8) | Cl1—Cu1—Cl1i | 105.28 (2) |
Symmetry code: (i) −x+3/2, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O3i | 0.91 (3) | 2.51 (3) | 3.288 (4) | 145 (3) |
C8—H8B···O3ii | 0.97 | 2.47 | 3.345 (3) | 150 |
C9—H9B···O2iii | 0.97 | 2.50 | 3.365 (4) | 148 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1, −y+2, −z. |
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Recently, we have reported a thiocyanate coordinated zinc(II) complex (Ye & You, 2007a) and a thiocyanate coordinated copper(II) complex (Ye & You, 2007b). As an extension of the work on the crystal structures of such complexes, we report herein the crystal structure of the title compound.
The title compound is a chloride-bridged polynuclear copper(II) complex (Fig. 1). The CuII atom is five-coordinated in a square-pyramidal geometry, with one O and two N atoms of the Schiff base ligand and one Cl atom defining the basal plane (Cu···Cl = 2.2703 (8) Å), and a symmetry-related Cl atom occupying the apical position (2.8531 (9) Å). Selected bond distances and angles within the coordination sphere of the metal atom are given in Table 1. The crystal structure is stabilized by N—H···O and and C—H···O hydrogen bonds (Table 2).