The title compound, [Cu(C
9H
13N
2O
2S)
2], is a centrosymmetric neutral complex with the Cu
II atom showing slightly distorted square-planar CuN
4 geometry. The crystal packing is consolidated by intramolecular N—H
O and intermolecular C—H
π interactions.
Supporting information
CCDC reference: 629838
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.037
- wR factor = 0.115
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ?
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... \P
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... \P
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
Bis[
N-(2-Aminoethyl)-4-methylbenzenesulfonamidato]copper(II)
top
Crystal data top
[Cu(C9H13N2O2S)2] | Z = 1 |
Mr = 490.09 | F(000) = 255 |
Triclinic, P1 | Dx = 1.544 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.6497 (6) Å | Cell parameters from 1963 reflections |
b = 7.8410 (9) Å | θ = 2.9–27.2° |
c = 13.2882 (15) Å | µ = 1.27 mm−1 |
α = 73.020 (1)° | T = 296 K |
β = 84.913 (1)° | Block, blue |
γ = 69.454 (1)° | 0.39 × 0.30 × 0.20 mm |
V = 527.12 (10) Å3 | |
Data collection top
Bruker SMART CCD diffractometer | 1848 independent reflections |
Radiation source: fine-focus sealed tube | 1715 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
ω scans | θmax = 25.1°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −6→6 |
Tmin = 0.641, Tmax = 0.785 | k = −9→5 |
2651 measured reflections | l = −15→15 |
Refinement top
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)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0885P)2 + 0.2074P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
1848 reflections | Δρmax = 0.54 e Å−3 |
122 parameters | Δρmin = −0.32 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: 0.044 (7) |
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 | 0.5000 | 0.0000 | 0.5000 | 0.0311 (2) | |
S1 | 0.85151 (12) | 0.25787 (9) | 0.37739 (5) | 0.0322 (2) | |
C1 | 0.7080 (3) | 0.4312 (2) | 0.25872 (11) | 0.0348 (6) | |
C2 | 0.8541 (3) | 0.4696 (3) | 0.17092 (14) | 0.0473 (7) | |
H2 | 1.0278 | 0.4059 | 0.1740 | 0.057* | |
C3 | 0.7407 (4) | 0.6030 (3) | 0.07849 (12) | 0.0587 (9) | |
H3 | 0.8385 | 0.6286 | 0.0197 | 0.070* | |
C4 | 0.4812 (4) | 0.6981 (3) | 0.07386 (13) | 0.0537 (8) | |
C5 | 0.3350 (3) | 0.6598 (3) | 0.16166 (17) | 0.0600 (9) | |
H5 | 0.1613 | 0.7234 | 0.1586 | 0.072* | |
C6 | 0.4484 (3) | 0.5263 (3) | 0.25409 (14) | 0.0540 (8) | |
H6 | 0.3506 | 0.5007 | 0.3128 | 0.065* | |
C7 | 0.3566 (10) | 0.8366 (6) | −0.0296 (3) | 0.0809 (13) | |
H7A | 0.4684 | 0.9028 | −0.0666 | 0.097* | |
H7B | 0.3131 | 0.7739 | −0.0709 | 0.097* | |
H7C | 0.2020 | 0.9348 | −0.0145 | 0.097* | |
C15 | 0.6812 (7) | −0.1390 (5) | 0.3259 (3) | 0.0542 (8) | |
H15A | 0.5292 | −0.0590 | 0.2842 | 0.065* | |
H15B | 0.7681 | −0.2434 | 0.2961 | 0.065* | |
C16 | 0.8490 (6) | −0.0266 (4) | 0.3237 (2) | 0.0402 (6) | |
H16A | 1.0190 | −0.1112 | 0.3465 | 0.048* | |
H16B | 0.8563 | 0.0521 | 0.2529 | 0.048* | |
N1 | 0.7419 (4) | 0.0933 (3) | 0.39569 (17) | 0.0324 (5) | |
N2 | 0.6151 (6) | −0.2118 (4) | 0.4343 (2) | 0.0499 (7) | |
H2A | 0.7483 | −0.3057 | 0.4703 | 0.060* | |
H2B | 0.4902 | −0.2583 | 0.4350 | 0.060* | |
O1 | 1.1211 (4) | 0.2002 (3) | 0.35687 (17) | 0.0459 (5) | |
O2 | 0.7704 (4) | 0.3508 (3) | 0.46061 (15) | 0.0435 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0376 (3) | 0.0289 (3) | 0.0326 (3) | −0.0187 (2) | 0.01089 (19) | −0.01106 (19) |
S1 | 0.0334 (4) | 0.0330 (4) | 0.0330 (4) | −0.0189 (3) | 0.0019 (3) | −0.0045 (3) |
C1 | 0.0395 (14) | 0.0299 (12) | 0.0370 (14) | −0.0179 (11) | −0.0006 (11) | −0.0046 (10) |
C2 | 0.0456 (16) | 0.0451 (16) | 0.0410 (15) | −0.0117 (13) | 0.0074 (12) | −0.0036 (12) |
C3 | 0.071 (2) | 0.0551 (19) | 0.0377 (17) | −0.0170 (17) | 0.0116 (15) | −0.0037 (14) |
C4 | 0.071 (2) | 0.0392 (16) | 0.0491 (18) | −0.0208 (15) | −0.0137 (15) | −0.0028 (13) |
C5 | 0.0429 (17) | 0.055 (2) | 0.070 (2) | −0.0161 (15) | −0.0105 (16) | 0.0014 (17) |
C6 | 0.0406 (16) | 0.0557 (19) | 0.0561 (19) | −0.0199 (14) | 0.0033 (14) | 0.0016 (15) |
C7 | 0.105 (3) | 0.061 (2) | 0.063 (2) | −0.024 (2) | −0.031 (2) | 0.0082 (18) |
C15 | 0.074 (2) | 0.0584 (19) | 0.0517 (18) | −0.0400 (17) | 0.0234 (16) | −0.0320 (16) |
C16 | 0.0465 (15) | 0.0419 (15) | 0.0363 (14) | −0.0213 (12) | 0.0144 (12) | −0.0135 (12) |
N1 | 0.0377 (11) | 0.0314 (11) | 0.0335 (11) | −0.0195 (9) | 0.0088 (9) | −0.0098 (9) |
N2 | 0.0694 (17) | 0.0383 (13) | 0.0553 (16) | −0.0337 (13) | 0.0294 (13) | −0.0222 (12) |
O1 | 0.0332 (10) | 0.0512 (12) | 0.0495 (12) | −0.0205 (9) | −0.0023 (8) | −0.0001 (9) |
O2 | 0.0600 (13) | 0.0427 (11) | 0.0405 (10) | −0.0322 (10) | 0.0053 (9) | −0.0138 (9) |
Geometric parameters (Å, º) top
Cu1—N2 | 1.983 (2) | C5—C6 | 1.3900 |
Cu1—N2i | 1.983 (2) | C5—H5 | 0.9300 |
Cu1—N1 | 2.024 (2) | C6—H6 | 0.9300 |
Cu1—N1i | 2.024 (2) | C7—H7A | 0.9669 |
S1—O2 | 1.453 (2) | C7—H7B | 0.9318 |
S1—O1 | 1.454 (2) | C7—H7C | 0.9914 |
S1—N1 | 1.568 (2) | C15—N2 | 1.454 (4) |
S1—C1 | 1.7869 (14) | C15—C16 | 1.498 (4) |
C1—C2 | 1.3900 | C15—H15A | 0.9700 |
C1—C6 | 1.3900 | C15—H15B | 0.9700 |
C2—C3 | 1.3900 | C16—N1 | 1.479 (3) |
C2—H2 | 0.9300 | C16—H16A | 0.9700 |
C3—C4 | 1.3900 | C16—H16B | 0.9700 |
C3—H3 | 0.9300 | N2—H2A | 0.8985 |
C4—C5 | 1.3900 | N2—H2B | 0.8988 |
C4—C7 | 1.526 (4) | | |
| | | |
N2—Cu1—N2i | 180.0 | C1—C6—H6 | 120.0 |
N1—Cu1—N1i | 180.0 | C4—C7—H7A | 109.6 |
N2—Cu1—N1 | 82.05 (9) | C4—C7—H7B | 111.0 |
N2i—Cu1—N1 | 97.95 (9) | H7A—C7—H7B | 111.3 |
N2—Cu1—N1i | 97.95 (9) | C4—C7—H7C | 109.3 |
N2i—Cu1—N1i | 82.05 (9) | H7A—C7—H7C | 106.3 |
O2—S1—O1 | 115.53 (13) | H7B—C7—H7C | 109.2 |
O2—S1—N1 | 109.88 (11) | N2—C15—C16 | 108.9 (3) |
O1—S1—N1 | 113.23 (12) | N2—C15—H15A | 109.9 |
O2—S1—C1 | 106.09 (11) | C16—C15—H15A | 109.9 |
O1—S1—C1 | 104.67 (10) | N2—C15—H15B | 109.9 |
N1—S1—C1 | 106.67 (11) | C16—C15—H15B | 109.9 |
C2—C1—C6 | 120.0 | H15A—C15—H15B | 108.3 |
C2—C1—S1 | 120.32 (10) | N1—C16—C15 | 107.7 (2) |
C6—C1—S1 | 119.68 (10) | N1—C16—H16A | 110.2 |
C1—C2—C3 | 120.0 | C15—C16—H16A | 110.2 |
C1—C2—H2 | 120.0 | N1—C16—H16B | 110.2 |
C3—C2—H2 | 120.0 | C15—C16—H16B | 110.2 |
C2—C3—C4 | 120.0 | H16A—C16—H16B | 108.5 |
C2—C3—H3 | 120.0 | C16—N1—S1 | 112.72 (17) |
C4—C3—H3 | 120.0 | C16—N1—Cu1 | 112.70 (16) |
C5—C4—C3 | 120.0 | S1—N1—Cu1 | 134.50 (13) |
C5—C4—C7 | 120.3 (2) | C15—N2—Cu1 | 108.32 (18) |
C3—C4—C7 | 119.6 (2) | C15—N2—H2A | 110.9 |
C6—C5—C4 | 120.0 | Cu1—N2—H2A | 110.1 |
C6—C5—H5 | 120.0 | C15—N2—H2B | 109.2 |
C4—C5—H5 | 120.0 | Cu1—N2—H2B | 110.0 |
C5—C6—C1 | 120.0 | H2A—N2—H2B | 108.4 |
C5—C6—H6 | 120.0 | | |
| | | |
O2—S1—C1—C2 | 127.82 (14) | C2—C1—C6—C5 | 0.0 |
O1—S1—C1—C2 | 5.19 (16) | S1—C1—C6—C5 | −179.25 (15) |
N1—S1—C1—C2 | −115.07 (14) | N2—C15—C16—N1 | −43.6 (3) |
O2—S1—C1—C6 | −52.94 (15) | C15—C16—N1—S1 | −163.7 (2) |
O1—S1—C1—C6 | −175.57 (14) | C15—C16—N1—Cu1 | 19.1 (3) |
N1—S1—C1—C6 | 64.17 (15) | O2—S1—N1—C16 | −170.96 (18) |
C6—C1—C2—C3 | 0.0 | O1—S1—N1—C16 | −40.1 (2) |
S1—C1—C2—C3 | 179.24 (15) | C1—S1—N1—C16 | 74.5 (2) |
C1—C2—C3—C4 | 0.0 | O2—S1—N1—Cu1 | 5.4 (2) |
C2—C3—C4—C5 | 0.0 | O1—S1—N1—Cu1 | 136.29 (17) |
C2—C3—C4—C7 | −176.8 (3) | C1—S1—N1—Cu1 | −109.13 (17) |
C3—C4—C5—C6 | 0.0 | N2i—Cu1—N1—S1 | 9.0 (2) |
C7—C4—C5—C6 | 176.8 (3) | C16—C15—N2—Cu1 | 48.6 (3) |
C4—C5—C6—C1 | 0.0 | N1i—Cu1—N2—C15 | 150.4 (2) |
Symmetry code: (i) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O2i | 0.90 | 2.10 | 2.849 (4) | 140 |
C7—H7B···πii | 0.93 | 3.13 | 3.989 (3) | 154 |
C15—H15B···πiii | 0.97 | 3.01 | 3.741 (4) | 161 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) x, y−1, z. |