metal-organic compounds
{2-[(2-Carbamoylhydrazin-1-ylidene)methyl-κ2N1,O]-5-methoxyphenolato-κO1}chloridocopper(II)
aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my
The 9H10N3O3)Cl], contains two independent molecules with similar structures. The CuII cation is N,O,O′-chelated by the deprotonated Schiff base ligand and is further coordinated by a Cl− anion in a distorted ClNO2 square-planar geometry. In the crystal, adjacent molecules are linked by N—H⋯O and N—H⋯Cl hydrogen bonds, forming a two-dimensional network parallel to [100].
of the title compound, [Cu(CExperimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2010); cell SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S160053681203574X/xu5610sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681203574X/xu5610Isup2.hkl
The Schiff base was prepared by heating 2-hydroxy-4-methoxybenzaldehyde (0.152 g,1 mmol) and semicarbazide hydrochloride (0.111 g,1 mmol) for 3 h. Copper(II) dichloride dihydrate (0.170 g, 1 mmol) was added to the solution and reflux was continued for another 2 h. Dark green colored crystals were isolated from the cool solution.
Carbon-bound H-atoms were placed in calculated positions (C–H 0.93 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2U(C). The amino H-atoms were similarly treated (N–H 0.88 Å).Data collection: APEX2 (Bruker, 2010); cell
SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of CuCl(C9H10N3O3) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
[Cu(C9H10N3O3)Cl] | F(000) = 1240 |
Mr = 307.19 | Dx = 1.821 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5495 reflections |
a = 11.8413 (6) Å | θ = 2.3–27.0° |
b = 14.2791 (7) Å | µ = 2.19 mm−1 |
c = 13.5751 (6) Å | T = 295 K |
β = 102.501 (2)° | Prism, dark green |
V = 2240.90 (19) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 8 |
Bruker Kappa APEXII diffractometer | 5562 independent reflections |
Radiation source: fine-focus sealed tube | 3809 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scans | θmax = 28.4°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.560, Tmax = 0.669 | k = −17→19 |
20852 measured reflections | l = −11→18 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0443P)2 + 2.0625P] where P = (Fo2 + 2Fc2)/3 |
5562 reflections | (Δ/σ)max = 0.001 |
307 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
[Cu(C9H10N3O3)Cl] | V = 2240.90 (19) Å3 |
Mr = 307.19 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.8413 (6) Å | µ = 2.19 mm−1 |
b = 14.2791 (7) Å | T = 295 K |
c = 13.5751 (6) Å | 0.30 × 0.25 × 0.20 mm |
β = 102.501 (2)° |
Bruker Kappa APEXII diffractometer | 5562 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3809 reflections with I > 2σ(I) |
Tmin = 0.560, Tmax = 0.669 | Rint = 0.047 |
20852 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.57 e Å−3 |
5562 reflections | Δρmin = −0.37 e Å−3 |
307 parameters |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.29935 (3) | 0.85386 (3) | 0.32124 (3) | 0.03357 (12) | |
Cu2 | 0.79752 (3) | 0.56618 (3) | 0.33325 (3) | 0.03219 (12) | |
Cl1 | 0.11883 (7) | 0.88631 (6) | 0.33195 (7) | 0.0418 (2) | |
Cl2 | 0.61629 (7) | 0.53124 (6) | 0.33804 (8) | 0.0509 (3) | |
O1 | 0.6111 (2) | 1.23052 (19) | 0.4410 (2) | 0.0569 (7) | |
O2 | 0.35126 (19) | 0.97847 (15) | 0.33806 (18) | 0.0365 (5) | |
O3 | 0.25915 (19) | 0.72346 (16) | 0.2833 (2) | 0.0446 (6) | |
O4 | 1.1173 (2) | 0.19137 (16) | 0.4510 (2) | 0.0488 (6) | |
O5 | 0.85178 (17) | 0.44138 (14) | 0.35581 (17) | 0.0334 (5) | |
O6 | 0.75675 (19) | 0.69642 (15) | 0.29078 (18) | 0.0380 (5) | |
N1 | 0.4534 (2) | 0.80675 (18) | 0.3315 (2) | 0.0324 (6) | |
N2 | 0.4528 (2) | 0.71236 (19) | 0.3109 (2) | 0.0396 (7) | |
H1 | 0.5168 | 0.6802 | 0.3132 | 0.048* | |
N3 | 0.3391 (3) | 0.58301 (19) | 0.2679 (3) | 0.0495 (8) | |
H2 | 0.2709 | 0.5559 | 0.2522 | 0.059* | |
H3 | 0.4023 | 0.5497 | 0.2710 | 0.059* | |
N4 | 0.9510 (2) | 0.61509 (17) | 0.34674 (18) | 0.0276 (5) | |
N5 | 0.9498 (2) | 0.70935 (17) | 0.3251 (2) | 0.0330 (6) | |
H4 | 1.0136 | 0.7425 | 0.3314 | 0.040* | |
N6 | 0.8360 (2) | 0.83611 (18) | 0.2675 (2) | 0.0400 (7) | |
H5 | 0.7678 | 0.8625 | 0.2471 | 0.048* | |
H6 | 0.8993 | 0.8692 | 0.2706 | 0.048* | |
C1 | 0.5869 (3) | 1.1399 (2) | 0.4154 (3) | 0.0409 (8) | |
C2 | 0.4767 (3) | 1.1034 (2) | 0.3879 (2) | 0.0357 (7) | |
H2A | 0.4132 | 1.1426 | 0.3843 | 0.043* | |
C3 | 0.4589 (3) | 1.0082 (2) | 0.3654 (2) | 0.0310 (7) | |
C4 | 0.5574 (3) | 0.9494 (2) | 0.3722 (2) | 0.0325 (7) | |
C5 | 0.6682 (3) | 0.9899 (3) | 0.3998 (3) | 0.0414 (8) | |
H5A | 0.7329 | 0.9519 | 0.4040 | 0.050* | |
C6 | 0.6834 (3) | 1.0825 (3) | 0.4205 (3) | 0.0459 (9) | |
H6A | 0.7576 | 1.1075 | 0.4380 | 0.055* | |
C7 | 0.5192 (4) | 1.2946 (3) | 0.4323 (3) | 0.0632 (12) | |
H7A | 0.5493 | 1.3555 | 0.4535 | 0.095* | |
H7B | 0.4679 | 1.2746 | 0.4741 | 0.095* | |
H7C | 0.4776 | 1.2974 | 0.3633 | 0.095* | |
C8 | 0.5499 (3) | 0.8510 (2) | 0.3526 (2) | 0.0340 (7) | |
H8 | 0.6179 | 0.8176 | 0.3552 | 0.041* | |
C9 | 0.3466 (3) | 0.6727 (2) | 0.2867 (3) | 0.0366 (7) | |
C10 | 1.0904 (3) | 0.2828 (2) | 0.4312 (2) | 0.0349 (7) | |
C11 | 0.9796 (3) | 0.3175 (2) | 0.4037 (2) | 0.0326 (7) | |
H11 | 0.9171 | 0.2770 | 0.3988 | 0.039* | |
C12 | 0.9595 (2) | 0.4135 (2) | 0.3829 (2) | 0.0268 (6) | |
C13 | 1.0564 (3) | 0.4741 (2) | 0.3919 (2) | 0.0291 (6) | |
C14 | 1.1674 (3) | 0.4347 (2) | 0.4214 (3) | 0.0376 (8) | |
H14 | 1.2313 | 0.4740 | 0.4279 | 0.045* | |
C15 | 1.1859 (3) | 0.3423 (2) | 0.4406 (3) | 0.0412 (8) | |
H15 | 1.2607 | 0.3188 | 0.4598 | 0.049* | |
C16 | 1.0267 (3) | 0.1256 (2) | 0.4431 (3) | 0.0516 (10) | |
H16A | 1.0587 | 0.0643 | 0.4593 | 0.077* | |
H16B | 0.9811 | 0.1257 | 0.3754 | 0.077* | |
H16C | 0.9788 | 0.1421 | 0.4891 | 0.077* | |
C17 | 1.0479 (3) | 0.5715 (2) | 0.3717 (2) | 0.0311 (7) | |
H17 | 1.1158 | 0.6056 | 0.3767 | 0.037* | |
C18 | 0.8432 (3) | 0.7473 (2) | 0.2934 (2) | 0.0322 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0244 (2) | 0.0258 (2) | 0.0503 (3) | −0.00060 (15) | 0.00748 (16) | −0.00107 (17) |
Cu2 | 0.0229 (2) | 0.0211 (2) | 0.0503 (3) | 0.00078 (14) | 0.00288 (16) | 0.00072 (16) |
Cl1 | 0.0258 (4) | 0.0332 (4) | 0.0670 (6) | −0.0013 (3) | 0.0116 (4) | −0.0007 (4) |
Cl2 | 0.0247 (4) | 0.0293 (4) | 0.0961 (8) | −0.0006 (3) | 0.0073 (4) | −0.0012 (4) |
O1 | 0.0594 (18) | 0.0400 (16) | 0.0694 (19) | −0.0185 (13) | 0.0099 (14) | −0.0094 (13) |
O2 | 0.0285 (12) | 0.0257 (12) | 0.0548 (15) | −0.0006 (9) | 0.0081 (10) | −0.0012 (10) |
O3 | 0.0277 (12) | 0.0296 (13) | 0.0749 (18) | −0.0020 (10) | 0.0079 (11) | −0.0087 (12) |
O4 | 0.0478 (16) | 0.0282 (13) | 0.0696 (18) | 0.0131 (11) | 0.0107 (12) | 0.0097 (12) |
O5 | 0.0226 (11) | 0.0229 (11) | 0.0524 (14) | 0.0008 (8) | 0.0031 (9) | −0.0013 (9) |
O6 | 0.0301 (12) | 0.0244 (12) | 0.0585 (15) | 0.0019 (9) | 0.0074 (10) | 0.0048 (10) |
N1 | 0.0311 (14) | 0.0290 (14) | 0.0372 (15) | 0.0004 (11) | 0.0075 (11) | −0.0017 (11) |
N2 | 0.0329 (15) | 0.0260 (14) | 0.0595 (19) | 0.0039 (11) | 0.0092 (13) | −0.0029 (13) |
N3 | 0.0340 (17) | 0.0280 (16) | 0.085 (2) | 0.0026 (12) | 0.0091 (15) | −0.0099 (15) |
N4 | 0.0266 (13) | 0.0216 (13) | 0.0342 (14) | −0.0005 (10) | 0.0056 (10) | 0.0025 (10) |
N5 | 0.0277 (14) | 0.0197 (13) | 0.0507 (17) | 0.0001 (10) | 0.0068 (11) | 0.0050 (11) |
N6 | 0.0308 (15) | 0.0249 (14) | 0.0628 (19) | 0.0023 (11) | 0.0072 (13) | 0.0098 (13) |
C1 | 0.048 (2) | 0.037 (2) | 0.0372 (19) | −0.0124 (16) | 0.0101 (15) | −0.0028 (15) |
C2 | 0.0386 (19) | 0.0313 (18) | 0.0373 (18) | −0.0030 (14) | 0.0085 (14) | 0.0019 (14) |
C3 | 0.0302 (17) | 0.0312 (17) | 0.0322 (17) | −0.0043 (13) | 0.0081 (12) | 0.0009 (13) |
C4 | 0.0277 (16) | 0.0359 (18) | 0.0348 (17) | −0.0039 (13) | 0.0086 (12) | 0.0009 (13) |
C5 | 0.0289 (18) | 0.047 (2) | 0.048 (2) | −0.0052 (15) | 0.0064 (14) | −0.0006 (16) |
C6 | 0.0335 (19) | 0.052 (2) | 0.050 (2) | −0.0151 (16) | 0.0043 (15) | −0.0052 (17) |
C7 | 0.086 (3) | 0.041 (2) | 0.060 (3) | −0.006 (2) | 0.011 (2) | −0.0008 (19) |
C8 | 0.0242 (16) | 0.0371 (19) | 0.0413 (19) | 0.0014 (13) | 0.0081 (13) | 0.0018 (14) |
C9 | 0.0308 (18) | 0.0292 (17) | 0.049 (2) | −0.0027 (13) | 0.0069 (14) | −0.0014 (15) |
C10 | 0.0394 (19) | 0.0269 (17) | 0.0378 (19) | 0.0088 (13) | 0.0071 (13) | 0.0021 (13) |
C11 | 0.0319 (17) | 0.0275 (17) | 0.0374 (18) | 0.0013 (12) | 0.0058 (13) | 0.0003 (13) |
C12 | 0.0248 (15) | 0.0261 (16) | 0.0287 (16) | 0.0025 (11) | 0.0042 (11) | −0.0012 (12) |
C13 | 0.0258 (16) | 0.0264 (16) | 0.0346 (17) | 0.0034 (12) | 0.0052 (12) | −0.0008 (12) |
C14 | 0.0257 (17) | 0.0343 (19) | 0.051 (2) | 0.0021 (13) | 0.0044 (14) | 0.0026 (15) |
C15 | 0.0286 (18) | 0.038 (2) | 0.056 (2) | 0.0098 (14) | 0.0055 (15) | 0.0082 (16) |
C16 | 0.060 (3) | 0.0251 (18) | 0.070 (3) | 0.0024 (17) | 0.015 (2) | 0.0074 (17) |
C17 | 0.0242 (16) | 0.0297 (17) | 0.0392 (18) | −0.0005 (12) | 0.0063 (12) | −0.0002 (13) |
C18 | 0.0305 (17) | 0.0270 (16) | 0.0397 (18) | 0.0024 (13) | 0.0087 (13) | −0.0001 (13) |
Cu1—O2 | 1.880 (2) | N6—H6 | 0.8800 |
Cu1—N1 | 1.920 (3) | C1—C2 | 1.380 (5) |
Cu1—O3 | 1.963 (2) | C1—C6 | 1.396 (5) |
Cu1—Cl1 | 2.2225 (9) | C2—C3 | 1.398 (4) |
Cu2—O5 | 1.897 (2) | C2—H2A | 0.9300 |
Cu2—N4 | 1.918 (2) | C3—C4 | 1.424 (4) |
Cu2—O6 | 1.976 (2) | C4—C5 | 1.408 (4) |
Cu2—Cl2 | 2.2179 (9) | C4—C8 | 1.429 (4) |
O1—C1 | 1.354 (4) | C5—C6 | 1.356 (5) |
O1—C7 | 1.408 (5) | C5—H5A | 0.9300 |
O2—C3 | 1.319 (4) | C6—H6A | 0.9300 |
O3—C9 | 1.257 (4) | C7—H7A | 0.9600 |
O4—C10 | 1.357 (4) | C7—H7B | 0.9600 |
O4—C16 | 1.412 (4) | C7—H7C | 0.9600 |
O5—C12 | 1.311 (3) | C8—H8 | 0.9300 |
O6—C18 | 1.250 (4) | C10—C11 | 1.376 (4) |
N1—C8 | 1.283 (4) | C10—C15 | 1.398 (5) |
N1—N2 | 1.376 (4) | C11—C12 | 1.409 (4) |
N2—C9 | 1.353 (4) | C11—H11 | 0.9300 |
N2—H1 | 0.8800 | C12—C13 | 1.422 (4) |
N3—C9 | 1.305 (4) | C13—C14 | 1.406 (4) |
N3—H2 | 0.8800 | C13—C17 | 1.417 (4) |
N3—H3 | 0.8800 | C14—C15 | 1.354 (4) |
N4—C17 | 1.284 (4) | C14—H14 | 0.9300 |
N4—N5 | 1.377 (3) | C15—H15 | 0.9300 |
N5—C18 | 1.355 (4) | C16—H16A | 0.9600 |
N5—H4 | 0.8800 | C16—H16B | 0.9600 |
N6—C18 | 1.314 (4) | C16—H16C | 0.9600 |
N6—H5 | 0.8800 | C17—H17 | 0.9300 |
O2—Cu1—N1 | 92.42 (10) | C6—C5—C4 | 122.0 (3) |
O2—Cu1—O3 | 169.71 (10) | C6—C5—H5A | 119.0 |
N1—Cu1—O3 | 81.91 (10) | C4—C5—H5A | 119.0 |
O2—Cu1—Cl1 | 95.08 (7) | C5—C6—C1 | 119.5 (3) |
N1—Cu1—Cl1 | 168.53 (8) | C5—C6—H6A | 120.3 |
O3—Cu1—Cl1 | 91.89 (7) | C1—C6—H6A | 120.3 |
O5—Cu2—N4 | 92.63 (10) | O1—C7—H7A | 109.5 |
O5—Cu2—O6 | 169.86 (10) | O1—C7—H7B | 109.5 |
N4—Cu2—O6 | 81.48 (10) | H7A—C7—H7B | 109.5 |
O5—Cu2—Cl2 | 94.59 (7) | O1—C7—H7C | 109.5 |
N4—Cu2—Cl2 | 169.05 (8) | H7A—C7—H7C | 109.5 |
O6—Cu2—Cl2 | 92.49 (7) | H7B—C7—H7C | 109.5 |
C1—O1—C7 | 118.8 (3) | N1—C8—C4 | 122.8 (3) |
C3—O2—Cu1 | 127.6 (2) | N1—C8—H8 | 118.6 |
C9—O3—Cu1 | 112.7 (2) | C4—C8—H8 | 118.6 |
C10—O4—C16 | 118.8 (3) | O3—C9—N3 | 122.5 (3) |
C12—O5—Cu2 | 127.32 (19) | O3—C9—N2 | 118.8 (3) |
C18—O6—Cu2 | 113.1 (2) | N3—C9—N2 | 118.6 (3) |
C8—N1—N2 | 119.5 (3) | O4—C10—C11 | 124.7 (3) |
C8—N1—Cu1 | 129.0 (2) | O4—C10—C15 | 114.6 (3) |
N2—N1—Cu1 | 111.46 (19) | C11—C10—C15 | 120.7 (3) |
C9—N2—N1 | 115.0 (3) | C10—C11—C12 | 120.9 (3) |
C9—N2—H1 | 122.5 | C10—C11—H11 | 119.5 |
N1—N2—H1 | 122.5 | C12—C11—H11 | 119.5 |
C9—N3—H2 | 120.0 | O5—C12—C11 | 117.6 (3) |
C9—N3—H3 | 120.0 | O5—C12—C13 | 123.9 (3) |
H2—N3—H3 | 120.0 | C11—C12—C13 | 118.5 (3) |
C17—N4—N5 | 119.8 (3) | C14—C13—C17 | 118.1 (3) |
C17—N4—Cu2 | 128.5 (2) | C14—C13—C12 | 117.9 (3) |
N5—N4—Cu2 | 111.69 (18) | C17—C13—C12 | 124.0 (3) |
C18—N5—N4 | 115.1 (2) | C15—C14—C13 | 123.2 (3) |
C18—N5—H4 | 122.4 | C15—C14—H14 | 118.4 |
N4—N5—H4 | 122.4 | C13—C14—H14 | 118.4 |
C18—N6—H5 | 120.0 | C14—C15—C10 | 118.7 (3) |
C18—N6—H6 | 120.0 | C14—C15—H15 | 120.6 |
H5—N6—H6 | 120.0 | C10—C15—H15 | 120.6 |
O1—C1—C2 | 124.5 (3) | O4—C16—H16A | 109.5 |
O1—C1—C6 | 115.0 (3) | O4—C16—H16B | 109.5 |
C2—C1—C6 | 120.5 (3) | H16A—C16—H16B | 109.5 |
C1—C2—C3 | 121.0 (3) | O4—C16—H16C | 109.5 |
C1—C2—H2A | 119.5 | H16A—C16—H16C | 109.5 |
C3—C2—H2A | 119.5 | H16B—C16—H16C | 109.5 |
O2—C3—C2 | 117.7 (3) | N4—C17—C13 | 123.3 (3) |
O2—C3—C4 | 123.8 (3) | N4—C17—H17 | 118.3 |
C2—C3—C4 | 118.5 (3) | C13—C17—H17 | 118.3 |
C5—C4—C3 | 118.5 (3) | O6—C18—N6 | 123.2 (3) |
C5—C4—C8 | 118.0 (3) | O6—C18—N5 | 118.5 (3) |
C3—C4—C8 | 123.4 (3) | N6—C18—N5 | 118.2 (3) |
N1—Cu1—O2—C3 | −10.5 (3) | C2—C3—C4—C8 | 179.0 (3) |
O3—Cu1—O2—C3 | −66.8 (7) | C3—C4—C5—C6 | 0.5 (5) |
Cl1—Cu1—O2—C3 | 160.8 (2) | C8—C4—C5—C6 | −179.5 (3) |
O2—Cu1—O3—C9 | 59.4 (7) | C4—C5—C6—C1 | 0.5 (5) |
N1—Cu1—O3—C9 | 2.3 (2) | O1—C1—C6—C5 | 177.6 (3) |
Cl1—Cu1—O3—C9 | −168.0 (2) | C2—C1—C6—C5 | −1.0 (5) |
N4—Cu2—O5—C12 | 7.3 (3) | N2—N1—C8—C4 | 178.3 (3) |
O6—Cu2—O5—C12 | 61.4 (6) | Cu1—N1—C8—C4 | −0.6 (5) |
Cl2—Cu2—O5—C12 | −164.5 (2) | C5—C4—C8—N1 | 176.7 (3) |
O5—Cu2—O6—C18 | −55.8 (6) | C3—C4—C8—N1 | −3.2 (5) |
N4—Cu2—O6—C18 | −0.9 (2) | Cu1—O3—C9—N3 | 177.4 (3) |
Cl2—Cu2—O6—C18 | 169.9 (2) | Cu1—O3—C9—N2 | −2.5 (4) |
O2—Cu1—N1—C8 | 5.9 (3) | N1—N2—C9—O3 | 1.1 (5) |
O3—Cu1—N1—C8 | 177.3 (3) | N1—N2—C9—N3 | −178.8 (3) |
Cl1—Cu1—N1—C8 | −124.9 (4) | C16—O4—C10—C11 | 0.3 (5) |
O2—Cu1—N1—N2 | −173.0 (2) | C16—O4—C10—C15 | −179.7 (3) |
O3—Cu1—N1—N2 | −1.7 (2) | O4—C10—C11—C12 | −179.0 (3) |
Cl1—Cu1—N1—N2 | 56.1 (5) | C15—C10—C11—C12 | 1.0 (5) |
C8—N1—N2—C9 | −178.2 (3) | Cu2—O5—C12—C11 | 174.7 (2) |
Cu1—N1—N2—C9 | 0.9 (3) | Cu2—O5—C12—C13 | −5.6 (4) |
O5—Cu2—N4—C17 | −5.5 (3) | C10—C11—C12—O5 | 179.1 (3) |
O6—Cu2—N4—C17 | −177.2 (3) | C10—C11—C12—C13 | −0.7 (4) |
Cl2—Cu2—N4—C17 | 125.8 (4) | O5—C12—C13—C14 | −179.8 (3) |
O5—Cu2—N4—N5 | 174.17 (19) | C11—C12—C13—C14 | −0.1 (4) |
O6—Cu2—N4—N5 | 2.46 (19) | O5—C12—C13—C17 | −0.7 (5) |
Cl2—Cu2—N4—N5 | −54.6 (5) | C11—C12—C13—C17 | 179.0 (3) |
C17—N4—N5—C18 | 175.9 (3) | C17—C13—C14—C15 | −178.6 (3) |
Cu2—N4—N5—C18 | −3.7 (3) | C12—C13—C14—C15 | 0.5 (5) |
C7—O1—C1—C2 | −5.1 (5) | C13—C14—C15—C10 | −0.2 (5) |
C7—O1—C1—C6 | 176.3 (3) | O4—C10—C15—C14 | 179.4 (3) |
O1—C1—C2—C3 | −178.0 (3) | C11—C10—C15—C14 | −0.6 (5) |
C6—C1—C2—C3 | 0.5 (5) | N5—N4—C17—C13 | −177.9 (3) |
Cu1—O2—C3—C2 | −170.5 (2) | Cu2—N4—C17—C13 | 1.7 (5) |
Cu1—O2—C3—C4 | 10.1 (4) | C14—C13—C17—N4 | −178.2 (3) |
C1—C2—C3—O2 | −178.9 (3) | C12—C13—C17—N4 | 2.7 (5) |
C1—C2—C3—C4 | 0.5 (5) | Cu2—O6—C18—N6 | 179.5 (3) |
O2—C3—C4—C5 | 178.4 (3) | Cu2—O6—C18—N5 | −1.0 (4) |
C2—C3—C4—C5 | −1.0 (4) | N4—N5—C18—O6 | 3.2 (4) |
O2—C3—C4—C8 | −1.6 (5) | N4—N5—C18—N6 | −177.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···Cl2 | 0.88 | 2.42 | 3.203 (3) | 149 |
N3—H2···O2i | 0.88 | 2.01 | 2.824 (4) | 153 |
N3—H3···Cl2 | 0.88 | 2.51 | 3.297 (3) | 149 |
N5—H4···Cl1ii | 0.88 | 2.40 | 3.212 (3) | 154 |
N6—H5···O5iii | 0.88 | 2.09 | 2.897 (3) | 152 |
N6—H6···Cl1ii | 0.88 | 2.56 | 3.351 (3) | 149 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C9H10N3O3)Cl] |
Mr | 307.19 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 11.8413 (6), 14.2791 (7), 13.5751 (6) |
β (°) | 102.501 (2) |
V (Å3) | 2240.90 (19) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 2.19 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.560, 0.669 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20852, 5562, 3809 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.110, 1.02 |
No. of reflections | 5562 |
No. of parameters | 307 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.57, −0.37 |
Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···Cl2 | 0.88 | 2.42 | 3.203 (3) | 148.5 |
N3—H2···O2i | 0.88 | 2.01 | 2.824 (4) | 153.0 |
N3—H3···Cl2 | 0.88 | 2.51 | 3.297 (3) | 148.6 |
N5—H4···Cl1ii | 0.88 | 2.40 | 3.212 (3) | 153.5 |
N6—H5···O5iii | 0.88 | 2.09 | 2.897 (3) | 152.2 |
N6—H6···Cl1ii | 0.88 | 2.56 | 3.351 (3) | 149.4 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) −x+3/2, y+1/2, −z+1/2. |
Acknowledgements
RJK thanks the University Grants Commission (India) for a Junior Research Fellowship. We thank the Sophisticated Analytical Instruments Facility, Cochin University of S & T, for the diffraction measurements. We also thank the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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Patole, J., Dutta, S., Padhye, S. & SInn, E. (2001). Inorg. Chim. Acta, 318, 207–211. Web of Science CSD CrossRef CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, J.-L., Liu, B., Yang, B.-S. & Huang, S.-P. (2008). J. Struct. Chem. 49, 570–574. Web of Science CrossRef CAS Google Scholar
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Salicylaldehyde thiosemicarbazone and its subsituted derivatives are Schiff bases that are capable of N,N',O-chelation to transition metal ions, a feature that has been documented in a plethora of metal derivatives. Several copper derivatives have been reported (Wang et al., 2008; Patole et al., 2001). The CuII atom in CuCl(C9H10N3O3) (Scheme I) is N,N',O-chelated by the deprotonated Schiff base, and it exists in a square planar environment in the two independent molecules (Fig. 1). Adjacent molecules are linked by N–H···O and N–H···Cl hydrogen bonds to form a two-dimensional network (Table 1).