Bis[N-(2-amino­ethyl)-4-methyl­benzene­sulfonamidato]copper(II)

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

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

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)

Crystal data

[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) Å^3

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0885P)^2 + 0.2074P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (7)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Cu1—N2	1.983 (2)	C5—C6	1.3900
Cu1—N2^i	1.983 (2)	C5—H5	0.9300
Cu1—N1	2.024 (2)	C6—H6	0.9300
Cu1—N1^i	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—N2^i	180.0	C1—C6—H6	120.0
N1—Cu1—N1^i	180.0	C4—C7—H7A	109.6
N2—Cu1—N1	82.05 (9)	C4—C7—H7B	111.0
N2^i—Cu1—N1	97.95 (9)	H7A—C7—H7B	111.3
N2—Cu1—N1^i	97.95 (9)	C4—C7—H7C	109.3
N2^i—Cu1—N1^i	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	N2^i—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	N1^i—Cu1—N2—C15	150.4 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2^i	0.90	2.10	2.849 (4)	140
C7—H7B···π^ii	0.93	3.13	3.989 (3)	154
C15—H15B···π^iii	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.