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The title compound, [Cu(C9H13N2O2S)2], is a centrosymmetric neutral complex with the CuII atom showing slightly distorted square-planar CuN4 geometry. The crystal packing is consolidated by intra­molecular N—H...O and inter­molecular C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046381/hb2192sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046381/hb2192Isup2.hkl
Contains datablock I

CCDC reference: 629838

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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

Computing details top

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 = 490.09F(000) = 255
Triclinic, P1Dx = 1.544 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.6497 (6) ÅCell parameters from 1963 reflections
b = 7.8410 (9) Åθ = 2.9–27.2°
c = 13.2882 (15) ŵ = 1.27 mm1
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 tube1715 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 66
Tmin = 0.641, Tmax = 0.785k = 95
2651 measured reflectionsl = 1515
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-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 reflectionsΔρmax = 0.54 e Å3
122 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
Cu10.50000.00000.50000.0311 (2)
S10.85151 (12)0.25787 (9)0.37739 (5)0.0322 (2)
C10.7080 (3)0.4312 (2)0.25872 (11)0.0348 (6)
C20.8541 (3)0.4696 (3)0.17092 (14)0.0473 (7)
H21.02780.40590.17400.057*
C30.7407 (4)0.6030 (3)0.07849 (12)0.0587 (9)
H30.83850.62860.01970.070*
C40.4812 (4)0.6981 (3)0.07386 (13)0.0537 (8)
C50.3350 (3)0.6598 (3)0.16166 (17)0.0600 (9)
H50.16130.72340.15860.072*
C60.4484 (3)0.5263 (3)0.25409 (14)0.0540 (8)
H60.35060.50070.31280.065*
C70.3566 (10)0.8366 (6)0.0296 (3)0.0809 (13)
H7A0.46840.90280.06660.097*
H7B0.31310.77390.07090.097*
H7C0.20200.93480.01450.097*
C150.6812 (7)0.1390 (5)0.3259 (3)0.0542 (8)
H15A0.52920.05900.28420.065*
H15B0.76810.24340.29610.065*
C160.8490 (6)0.0266 (4)0.3237 (2)0.0402 (6)
H16A1.01900.11120.34650.048*
H16B0.85630.05210.25290.048*
N10.7419 (4)0.0933 (3)0.39569 (17)0.0324 (5)
N20.6151 (6)0.2118 (4)0.4343 (2)0.0499 (7)
H2A0.74830.30570.47030.060*
H2B0.49020.25830.43500.060*
O11.1211 (4)0.2002 (3)0.35687 (17)0.0459 (5)
O20.7704 (4)0.3508 (3)0.46061 (15)0.0435 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0376 (3)0.0289 (3)0.0326 (3)0.0187 (2)0.01089 (19)0.01106 (19)
S10.0334 (4)0.0330 (4)0.0330 (4)0.0189 (3)0.0019 (3)0.0045 (3)
C10.0395 (14)0.0299 (12)0.0370 (14)0.0179 (11)0.0006 (11)0.0046 (10)
C20.0456 (16)0.0451 (16)0.0410 (15)0.0117 (13)0.0074 (12)0.0036 (12)
C30.071 (2)0.0551 (19)0.0377 (17)0.0170 (17)0.0116 (15)0.0037 (14)
C40.071 (2)0.0392 (16)0.0491 (18)0.0208 (15)0.0137 (15)0.0028 (13)
C50.0429 (17)0.055 (2)0.070 (2)0.0161 (15)0.0105 (16)0.0014 (17)
C60.0406 (16)0.0557 (19)0.0561 (19)0.0199 (14)0.0033 (14)0.0016 (15)
C70.105 (3)0.061 (2)0.063 (2)0.024 (2)0.031 (2)0.0082 (18)
C150.074 (2)0.0584 (19)0.0517 (18)0.0400 (17)0.0234 (16)0.0320 (16)
C160.0465 (15)0.0419 (15)0.0363 (14)0.0213 (12)0.0144 (12)0.0135 (12)
N10.0377 (11)0.0314 (11)0.0335 (11)0.0195 (9)0.0088 (9)0.0098 (9)
N20.0694 (17)0.0383 (13)0.0553 (16)0.0337 (13)0.0294 (13)0.0222 (12)
O10.0332 (10)0.0512 (12)0.0495 (12)0.0205 (9)0.0023 (8)0.0001 (9)
O20.0600 (13)0.0427 (11)0.0405 (10)0.0322 (10)0.0053 (9)0.0138 (9)
Geometric parameters (Å, º) top
Cu1—N21.983 (2)C5—C61.3900
Cu1—N2i1.983 (2)C5—H50.9300
Cu1—N12.024 (2)C6—H60.9300
Cu1—N1i2.024 (2)C7—H7A0.9669
S1—O21.453 (2)C7—H7B0.9318
S1—O11.454 (2)C7—H7C0.9914
S1—N11.568 (2)C15—N21.454 (4)
S1—C11.7869 (14)C15—C161.498 (4)
C1—C21.3900C15—H15A0.9700
C1—C61.3900C15—H15B0.9700
C2—C31.3900C16—N11.479 (3)
C2—H20.9300C16—H16A0.9700
C3—C41.3900C16—H16B0.9700
C3—H30.9300N2—H2A0.8985
C4—C51.3900N2—H2B0.8988
C4—C71.526 (4)
N2—Cu1—N2i180.0C1—C6—H6120.0
N1—Cu1—N1i180.0C4—C7—H7A109.6
N2—Cu1—N182.05 (9)C4—C7—H7B111.0
N2i—Cu1—N197.95 (9)H7A—C7—H7B111.3
N2—Cu1—N1i97.95 (9)C4—C7—H7C109.3
N2i—Cu1—N1i82.05 (9)H7A—C7—H7C106.3
O2—S1—O1115.53 (13)H7B—C7—H7C109.2
O2—S1—N1109.88 (11)N2—C15—C16108.9 (3)
O1—S1—N1113.23 (12)N2—C15—H15A109.9
O2—S1—C1106.09 (11)C16—C15—H15A109.9
O1—S1—C1104.67 (10)N2—C15—H15B109.9
N1—S1—C1106.67 (11)C16—C15—H15B109.9
C2—C1—C6120.0H15A—C15—H15B108.3
C2—C1—S1120.32 (10)N1—C16—C15107.7 (2)
C6—C1—S1119.68 (10)N1—C16—H16A110.2
C1—C2—C3120.0C15—C16—H16A110.2
C1—C2—H2120.0N1—C16—H16B110.2
C3—C2—H2120.0C15—C16—H16B110.2
C2—C3—C4120.0H16A—C16—H16B108.5
C2—C3—H3120.0C16—N1—S1112.72 (17)
C4—C3—H3120.0C16—N1—Cu1112.70 (16)
C5—C4—C3120.0S1—N1—Cu1134.50 (13)
C5—C4—C7120.3 (2)C15—N2—Cu1108.32 (18)
C3—C4—C7119.6 (2)C15—N2—H2A110.9
C6—C5—C4120.0Cu1—N2—H2A110.1
C6—C5—H5120.0C15—N2—H2B109.2
C4—C5—H5120.0Cu1—N2—H2B110.0
C5—C6—C1120.0H2A—N2—H2B108.4
C5—C6—H6120.0
O2—S1—C1—C2127.82 (14)C2—C1—C6—C50.0
O1—S1—C1—C25.19 (16)S1—C1—C6—C5179.25 (15)
N1—S1—C1—C2115.07 (14)N2—C15—C16—N143.6 (3)
O2—S1—C1—C652.94 (15)C15—C16—N1—S1163.7 (2)
O1—S1—C1—C6175.57 (14)C15—C16—N1—Cu119.1 (3)
N1—S1—C1—C664.17 (15)O2—S1—N1—C16170.96 (18)
C6—C1—C2—C30.0O1—S1—N1—C1640.1 (2)
S1—C1—C2—C3179.24 (15)C1—S1—N1—C1674.5 (2)
C1—C2—C3—C40.0O2—S1—N1—Cu15.4 (2)
C2—C3—C4—C50.0O1—S1—N1—Cu1136.29 (17)
C2—C3—C4—C7176.8 (3)C1—S1—N1—Cu1109.13 (17)
C3—C4—C5—C60.0N2i—Cu1—N1—S19.0 (2)
C7—C4—C5—C6176.8 (3)C16—C15—N2—Cu148.6 (3)
C4—C5—C6—C10.0N1i—Cu1—N2—C15150.4 (2)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O2i0.902.102.849 (4)140
C7—H7B···πii0.933.133.989 (3)154
C15—H15B···πiii0.973.013.741 (4)161
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z; (iii) x, y1, z.
 

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