The title complex, [Cu(C12H9N2O2S)Cl]·H2O, features a square-planar CuII centre coordinated by two O atoms and an N atom derived from the tridentate ligand, and a Cl atom. The complex molecules stack in layers which are held together by hydrogen bonds involving the water molecules of crystallization.
Supporting information
CCDC reference: 610910
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.088
- 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 ..................... 0.88
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 2
O2 -CU1 -O1 -C1 -26.60 0.60 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4
O1 -CU1 -O2 -C8 32.60 0.50 1.555 1.555 1.555 1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 0.881
Tmax scaled 0.423 Tmin scaled 0.326
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 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
2 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Chloro(2-oxidobenzaldehyde 2-thienylcarbonylhydrazone)copper(II) monohydrate
top
Crystal data top
[Cu(C12H9N2O2S)Cl]·H2O | F(000) = 732 |
Mr = 362.28 | Dx = 1.724 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3676 reflections |
a = 11.9991 (9) Å | θ = 3.1–27.5° |
b = 7.1804 (5) Å | µ = 1.91 mm−1 |
c = 16.2195 (11) Å | T = 293 K |
β = 92.646 (3)° | Prism, blue |
V = 1395.96 (17) Å3 | 0.65 × 0.55 × 0.45 mm |
Z = 4 | |
Data collection top
Bruker P4 diffractometer | 3187 independent reflections |
Radiation source: fine-focus sealed tube | 2840 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→15 |
Tmin = 0.370, Tmax = 0.480 | k = −9→9 |
10148 measured reflections | l = −18→21 |
Refinement top
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)] = 0.030 | Hydrogen site location: mixed |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0564P)2 + 0.4954P] where P = (Fo2 + 2Fc2)/3 |
3187 reflections | (Δ/σ)max = 0.001 |
185 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.634795 (18) | 0.17957 (3) | −0.055216 (13) | 0.03413 (10) | |
S1 | 0.96756 (5) | −0.03909 (10) | 0.11189 (4) | 0.05489 (17) | |
O1 | 0.50003 (12) | 0.2748 (2) | −0.10470 (8) | 0.0405 (3) | |
O2 | 0.76956 (11) | 0.0992 (2) | 0.01027 (8) | 0.0407 (3) | |
N2 | 0.65191 (13) | 0.1235 (2) | 0.11353 (9) | 0.0345 (3) | |
H2A | 0.6366 | 0.1141 | 0.1647 | 0.041* | |
N1 | 0.57575 (13) | 0.1850 (2) | 0.05390 (9) | 0.0315 (3) | |
C1 | 0.40841 (16) | 0.3239 (3) | −0.06813 (12) | 0.0331 (4) | |
C2 | 0.31768 (17) | 0.3920 (3) | −0.11726 (13) | 0.0420 (5) | |
H2B | 0.3235 | 0.3984 | −0.1742 | 0.050* | |
C3 | 0.22105 (18) | 0.4491 (3) | −0.08338 (15) | 0.0471 (5) | |
H3A | 0.1627 | 0.4943 | −0.1174 | 0.057* | |
C4 | 0.20905 (19) | 0.4401 (4) | 0.00138 (16) | 0.0533 (6) | |
H4A | 0.1435 | 0.4805 | 0.0241 | 0.064* | |
C5 | 0.29408 (19) | 0.3719 (4) | 0.05076 (14) | 0.0474 (5) | |
H5A | 0.2855 | 0.3646 | 0.1074 | 0.057* | |
C6 | 0.39521 (16) | 0.3118 (3) | 0.01827 (12) | 0.0341 (4) | |
C7 | 0.47961 (16) | 0.2434 (3) | 0.07539 (11) | 0.0349 (4) | |
H7A | 0.4645 | 0.2408 | 0.1311 | 0.042* | |
C8 | 0.75199 (16) | 0.0794 (3) | 0.08566 (11) | 0.0344 (4) | |
C9 | 0.83662 (16) | 0.0100 (3) | 0.14420 (12) | 0.0363 (4) | |
C10 | 0.82744 (19) | −0.0347 (3) | 0.22631 (13) | 0.0467 (5) | |
H10A | 0.7630 | −0.0182 | 0.2552 | 0.056* | |
C11 | 0.9269 (2) | −0.1078 (4) | 0.26084 (16) | 0.0601 (7) | |
H11A | 0.9357 | −0.1457 | 0.3156 | 0.072* | |
C12 | 1.0088 (2) | −0.1178 (4) | 0.20698 (17) | 0.0602 (6) | |
H12A | 1.0800 | −0.1628 | 0.2204 | 0.072* | |
Cl1 | 0.70066 (4) | 0.11209 (10) | −0.17675 (3) | 0.05080 (16) | |
O3 | 0.45205 (12) | 0.5115 (2) | 0.24602 (8) | 0.0461 (4) | |
HW1 | 0.4667 | 0.5791 | 0.2088 | 0.055* | |
HW2 | 0.5086 | 0.4757 | 0.2606 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.03654 (15) | 0.04267 (17) | 0.02327 (14) | −0.00355 (9) | 0.00229 (9) | −0.00043 (8) |
S1 | 0.0416 (3) | 0.0700 (4) | 0.0535 (3) | 0.0048 (3) | 0.0077 (2) | 0.0032 (3) |
O1 | 0.0400 (7) | 0.0561 (9) | 0.0255 (6) | −0.0007 (6) | 0.0025 (5) | 0.0033 (6) |
O2 | 0.0402 (7) | 0.0521 (9) | 0.0299 (7) | 0.0009 (6) | 0.0039 (5) | 0.0016 (6) |
N2 | 0.0402 (8) | 0.0395 (9) | 0.0236 (7) | 0.0029 (7) | 0.0004 (6) | 0.0018 (6) |
N1 | 0.0370 (8) | 0.0329 (8) | 0.0244 (7) | −0.0019 (6) | −0.0001 (6) | −0.0010 (6) |
C1 | 0.0366 (9) | 0.0312 (9) | 0.0314 (9) | −0.0073 (7) | 0.0005 (7) | 0.0004 (7) |
C2 | 0.0435 (10) | 0.0460 (12) | 0.0360 (10) | −0.0064 (9) | −0.0034 (8) | 0.0054 (9) |
C3 | 0.0409 (11) | 0.0471 (13) | 0.0524 (12) | 0.0000 (9) | −0.0084 (9) | 0.0050 (10) |
C4 | 0.0419 (11) | 0.0613 (15) | 0.0569 (14) | 0.0109 (10) | 0.0050 (10) | −0.0019 (11) |
C5 | 0.0477 (12) | 0.0558 (14) | 0.0392 (11) | 0.0078 (10) | 0.0078 (9) | −0.0028 (10) |
C6 | 0.0389 (10) | 0.0319 (10) | 0.0315 (9) | −0.0017 (7) | 0.0022 (7) | −0.0034 (7) |
C7 | 0.0444 (10) | 0.0359 (10) | 0.0248 (8) | −0.0009 (8) | 0.0048 (7) | −0.0019 (7) |
C8 | 0.0406 (9) | 0.0311 (10) | 0.0313 (9) | −0.0045 (7) | 0.0005 (7) | −0.0016 (7) |
C9 | 0.0365 (9) | 0.0370 (10) | 0.0354 (9) | −0.0001 (8) | 0.0010 (7) | −0.0001 (8) |
C10 | 0.0455 (11) | 0.0565 (14) | 0.0381 (10) | 0.0094 (10) | 0.0010 (9) | 0.0067 (10) |
C11 | 0.0572 (14) | 0.0728 (18) | 0.0495 (13) | 0.0128 (13) | −0.0066 (11) | 0.0161 (13) |
C12 | 0.0443 (12) | 0.0674 (17) | 0.0680 (16) | 0.0115 (12) | −0.0081 (11) | 0.0063 (14) |
Cl1 | 0.0439 (3) | 0.0795 (4) | 0.0296 (2) | 0.0004 (3) | 0.0072 (2) | −0.0082 (2) |
O3 | 0.0459 (8) | 0.0631 (10) | 0.0296 (7) | 0.0074 (7) | 0.0042 (6) | 0.0045 (7) |
Geometric parameters (Å, º) top
Cu1—Cl1 | 2.2111 (5) | C3—H3A | 0.9300 |
Cu1—O1 | 1.8991 (14) | C4—C5 | 1.359 (3) |
Cu1—O2 | 1.9793 (14) | C4—H4A | 0.9300 |
Cu1—N1 | 1.9369 (15) | C5—C6 | 1.413 (3) |
S1—C12 | 1.695 (3) | C5—H5A | 0.9300 |
S1—C9 | 1.716 (2) | C6—C7 | 1.428 (3) |
O1—C1 | 1.321 (2) | C7—H7A | 0.9300 |
O2—C8 | 1.259 (2) | C8—C9 | 1.446 (3) |
N2—C8 | 1.340 (2) | C9—C10 | 1.379 (3) |
N2—N1 | 1.373 (2) | C10—C11 | 1.397 (3) |
N2—H2A | 0.8600 | C10—H10A | 0.9300 |
N1—C7 | 1.290 (2) | C11—C12 | 1.347 (4) |
C1—C2 | 1.407 (3) | C11—H11A | 0.9300 |
C1—C6 | 1.420 (3) | C12—H12A | 0.9300 |
C2—C3 | 1.369 (3) | O3—HW1 | 0.8000 |
C2—H2B | 0.9300 | O3—HW2 | 0.7537 |
C3—C4 | 1.390 (3) | | |
| | | |
Cl1—Cu1—O1 | 91.98 (4) | C3—C4—H4A | 120.3 |
Cl1—Cu1—O2 | 95.61 (4) | C4—C5—C6 | 121.7 (2) |
Cl1—Cu1—N1 | 168.50 (5) | C4—C5—H5A | 119.2 |
O1—Cu1—O2 | 172.05 (6) | C6—C5—H5A | 119.2 |
O1—Cu1—N1 | 92.21 (6) | C5—C6—C1 | 119.09 (18) |
O2—Cu1—N1 | 80.79 (6) | C5—C6—C7 | 117.30 (18) |
C12—S1—C9 | 91.36 (11) | C1—C6—C7 | 123.60 (18) |
C1—O1—Cu1 | 128.06 (12) | N1—C7—C6 | 123.54 (17) |
C8—O2—Cu1 | 112.64 (12) | N1—C7—H7A | 118.2 |
C8—N2—N1 | 114.59 (15) | C6—C7—H7A | 118.2 |
C8—N2—H2A | 122.7 | O2—C8—N2 | 119.60 (17) |
N1—N2—H2A | 122.7 | O2—C8—C9 | 122.18 (18) |
C7—N1—N2 | 119.25 (15) | N2—C8—C9 | 118.22 (17) |
C7—N1—Cu1 | 128.52 (13) | C10—C9—C8 | 128.98 (19) |
N2—N1—Cu1 | 112.18 (12) | C10—C9—S1 | 111.24 (16) |
O1—C1—C2 | 118.48 (17) | C8—C9—S1 | 119.70 (15) |
O1—C1—C6 | 124.03 (18) | C9—C10—C11 | 111.7 (2) |
C2—C1—C6 | 117.49 (18) | C9—C10—H10A | 124.2 |
C3—C2—C1 | 121.63 (19) | C11—C10—H10A | 124.2 |
C3—C2—H2B | 119.2 | C12—C11—C10 | 113.3 (2) |
C1—C2—H2B | 119.2 | C12—C11—H11A | 123.3 |
C2—C3—C4 | 120.8 (2) | C10—C11—H11A | 123.3 |
C2—C3—H3A | 119.6 | C11—C12—S1 | 112.41 (19) |
C4—C3—H3A | 119.6 | C11—C12—H12A | 123.8 |
C5—C4—C3 | 119.3 (2) | S1—C12—H12A | 123.8 |
C5—C4—H4A | 120.3 | HW1—O3—HW2 | 102.6 |
| | | |
N1—Cu1—O1—C1 | 1.43 (17) | O1—C1—C6—C5 | 178.76 (19) |
O2—Cu1—O1—C1 | −26.6 (6) | C2—C1—C6—C5 | −1.5 (3) |
Cl1—Cu1—O1—C1 | 170.72 (16) | O1—C1—C6—C7 | −0.5 (3) |
O1—Cu1—O2—C8 | 32.6 (5) | C2—C1—C6—C7 | 179.25 (19) |
N1—Cu1—O2—C8 | 4.10 (14) | N2—N1—C7—C6 | 179.36 (17) |
Cl1—Cu1—O2—C8 | −164.89 (14) | Cu1—N1—C7—C6 | 2.2 (3) |
C8—N2—N1—C7 | −175.12 (18) | C5—C6—C7—N1 | −179.7 (2) |
C8—N2—N1—Cu1 | 2.5 (2) | C1—C6—C7—N1 | −0.4 (3) |
O1—Cu1—N1—C7 | −2.35 (18) | Cu1—O2—C8—N2 | −4.0 (2) |
O2—Cu1—N1—C7 | 173.87 (18) | Cu1—O2—C8—C9 | 175.93 (15) |
Cl1—Cu1—N1—C7 | −113.7 (3) | N1—N2—C8—O2 | 1.1 (3) |
O1—Cu1—N1—N2 | −179.68 (13) | N1—N2—C8—C9 | −178.87 (16) |
O2—Cu1—N1—N2 | −3.46 (12) | O2—C8—C9—C10 | −173.6 (2) |
Cl1—Cu1—N1—N2 | 69.0 (3) | N2—C8—C9—C10 | 6.3 (3) |
Cu1—O1—C1—C2 | 179.84 (15) | O2—C8—C9—S1 | 2.7 (3) |
Cu1—O1—C1—C6 | −0.4 (3) | N2—C8—C9—S1 | −177.37 (15) |
O1—C1—C2—C3 | −178.6 (2) | C12—S1—C9—C10 | −0.1 (2) |
C6—C1—C2—C3 | 1.6 (3) | C12—S1—C9—C8 | −176.96 (19) |
C1—C2—C3—C4 | −0.5 (4) | C8—C9—C10—C11 | 176.5 (2) |
C2—C3—C4—C5 | −0.7 (4) | S1—C9—C10—C11 | 0.0 (3) |
C3—C4—C5—C6 | 0.8 (4) | C9—C10—C11—C12 | 0.2 (4) |
C4—C5—C6—C1 | 0.3 (3) | C10—C11—C12—S1 | −0.2 (4) |
C4—C5—C6—C7 | 179.6 (2) | C9—S1—C12—C11 | 0.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2a···O3i | 0.86 | 1.98 | 2.767 (2) | 152 |
O3—Hw1···O1ii | 0.80 | 2.04 | 2.839 (2) | 173 |
O3—Hw2···Cl1iii | 0.75 | 2.55 | 3.3030 (16) | 173 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x, −y+1/2, z+1/2. |