trans-Bis­(ethyl­enedi­amine)­bis(p-nitro­benzoxasulfamato)copper(II)

The structure of trans-[Cu(nbs)₂(en)₂] [nbs is the p-nitro­benzoxasulfamate anion (C₆H₃N₂O₅S)⁻ and en is ethyl­enedi­amine, C₂H₈N₂] consists of neutral mol­ecules. The Cu²⁺ ion occupies an inversion centre and exhibits an elongated distorted octahedral geometry, with two monodentate nbs anions and two bidentate en ligands. Both nbs ligands are O-coordinated via an O atom of the nitro group. The crystal structure is stabilized by hydrogen bonds and weak aromatic π–π stacking interactions between the benzene rings of nbs ligands, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.091
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

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Alert level C
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         O1
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         O3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

trans-Bis(ethylenediamine)bis(p-nitrobenzoxasulfamato)copper(II)

Crystal data

[Cu(C6H3N2O5S)2(C2H8N2)2]	F(000) = 1260
Mr = 614.08	Dx = 1.788 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 14720 reflections
a = 10.2967 (11) Å	θ = 2.4–29.4°
b = 14.4563 (9) Å	µ = 1.21 mm^−1
c = 15.3929 (14) Å	T = 293 K
β = 95.429 (8)°	Plate, brown
V = 2281.0 (4) Å^3	0.6 × 0.3 × 0.07 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	2132 independent reflections
Radiation source: fine-focus sealed tube	1472 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 6.67 pixels mm^-1	θmax = 25.5°, θmin = 2.4°
rotation method scans	h = −12→12
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = 0→17
Tmin = 0.652, Tmax = 0.919	l = 0→18
2132 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0547P)^2] where P = (Fo^2 + 2Fc^2)/3
2132 reflections	(Δ/σ)max = 0.001
169 parameters	Δρmax = 0.76 e Å^−3
4 restraints	Δρmin = −0.54 e Å^−3

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	0.0000	0.5000	0.5000	0.03196 (18)
S1	0.77516 (9)	0.36324 (6)	0.73605 (6)	0.0363 (2)
N1	−0.0191 (3)	0.63429 (19)	0.46840 (19)	0.0388 (7)
H1A	0.0587	0.6580	0.4579	0.047*
H1B	−0.0745	0.6409	0.4200	0.047*
N2	−0.0031 (3)	0.5453 (2)	0.62321 (18)	0.0359 (7)
H2A	−0.0751	0.5240	0.6455	0.043*
H2B	0.0671	0.5236	0.6562	0.043*
N3	0.3199 (3)	0.5700 (2)	0.5456 (2)	0.0446 (8)
N4	0.6292 (2)	0.35022 (16)	0.68446 (17)	0.0288 (6)
O1	0.2486 (3)	0.5052 (2)	0.51681 (18)	0.0564 (7)
O2	0.2922 (3)	0.6511 (2)	0.5301 (2)	0.0743 (10)
O3	0.7804 (3)	0.47299 (18)	0.7409 (2)	0.0560 (7)
O4	0.8651 (3)	0.3247 (2)	0.68252 (18)	0.0580 (8)
O5	0.7716 (3)	0.32032 (18)	0.81904 (16)	0.0490 (7)
C1	−0.0699 (5)	0.6830 (3)	0.5420 (2)	0.0543 (11)
H1C	−0.1632	0.6729	0.5411	0.065*
H1D	−0.0547	0.7490	0.5372	0.065*
C2	−0.0026 (5)	0.6474 (3)	0.6254 (3)	0.0520 (10)
H2C	0.0865	0.6700	0.6326	0.062*
H2D	−0.0472	0.6691	0.6743	0.062*
C3	0.4390 (3)	0.5476 (2)	0.5972 (2)	0.0329 (8)
C4	0.5194 (4)	0.6185 (2)	0.6314 (2)	0.0384 (8)
H4	0.4951	0.6799	0.6214	0.046*
C5	0.6347 (3)	0.5980 (2)	0.6798 (2)	0.0378 (8)
H5	0.6891	0.6453	0.7023	0.045*
C6	0.6694 (3)	0.5065 (2)	0.6949 (2)	0.0320 (7)
C7	0.5823 (3)	0.4375 (2)	0.6614 (2)	0.0296 (7)
C8	0.4685 (3)	0.4548 (2)	0.6127 (2)	0.0335 (8)
H8	0.4134	0.4075	0.5908	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0395 (3)	0.0272 (3)	0.0281 (3)	0.0029 (3)	−0.0025 (2)	0.0006 (3)
S1	0.0365 (5)	0.0338 (4)	0.0372 (5)	0.0054 (4)	−0.0040 (4)	−0.0016 (4)
N1	0.0488 (18)	0.0319 (15)	0.0349 (15)	0.0037 (14)	−0.0007 (13)	0.0020 (12)
N2	0.0392 (16)	0.0359 (16)	0.0317 (15)	0.0015 (13)	−0.0013 (13)	0.0023 (13)
N3	0.0428 (18)	0.052 (2)	0.0385 (17)	0.0086 (16)	−0.0005 (14)	0.0004 (15)
N4	0.0332 (12)	0.0116 (10)	0.0395 (15)	0.0000 (10)	−0.0072 (11)	−0.0024 (11)
O1	0.0400 (14)	0.0654 (19)	0.0611 (17)	0.0040 (15)	−0.0099 (12)	−0.0030 (16)
O2	0.077 (2)	0.0532 (19)	0.086 (2)	0.0238 (16)	−0.0279 (18)	0.0067 (17)
O3	0.0528 (16)	0.0387 (9)	0.0725 (19)	−0.0009 (12)	−0.0150 (13)	0.0001 (13)
O4	0.0558 (17)	0.0654 (18)	0.0533 (17)	0.0195 (14)	0.0066 (14)	−0.0099 (15)
O5	0.0623 (17)	0.0409 (14)	0.0424 (14)	0.0056 (13)	−0.0028 (13)	0.0072 (12)
C1	0.082 (3)	0.037 (2)	0.044 (2)	0.017 (2)	0.005 (2)	−0.0029 (18)
C2	0.074 (3)	0.037 (2)	0.044 (2)	0.001 (2)	0.002 (2)	−0.0065 (18)
C3	0.0315 (18)	0.037 (2)	0.0303 (18)	0.0054 (15)	0.0009 (15)	0.0015 (14)
C4	0.049 (2)	0.0263 (18)	0.040 (2)	0.0042 (15)	0.0040 (17)	0.0027 (15)
C5	0.045 (2)	0.0230 (16)	0.045 (2)	−0.0065 (15)	0.0015 (16)	−0.0008 (15)
C6	0.0360 (15)	0.0300 (16)	0.0301 (16)	−0.0056 (14)	0.0039 (12)	−0.0024 (15)
C7	0.0360 (18)	0.0180 (13)	0.0344 (17)	0.0035 (12)	0.0007 (14)	0.0015 (13)
C8	0.0312 (18)	0.0347 (19)	0.0340 (19)	−0.0020 (14)	0.0003 (15)	−0.0048 (15)

Geometric parameters (Å, º)

Cu1—N1^i	2.007 (3)	N3—C3	1.434 (4)
Cu1—N1	2.007 (3)	N4—C7	1.385 (4)
Cu1—N2^i	2.010 (3)	O3—C6	1.374 (4)
Cu1—N2	2.010 (3)	C1—C2	1.491 (5)
Cu1—O1^i	2.550 (3)	C1—H1C	0.9700
Cu1—O1	2.550 (3)	C1—H1D	0.9700
S1—O4	1.412 (3)	C2—H2C	0.9700
S1—O5	1.424 (3)	C2—H2D	0.9700
S1—O3	1.589 (3)	C3—C8	1.391 (5)
S1—N4	1.643 (3)	C3—C4	1.390 (5)
N1—C1	1.472 (5)	C4—C5	1.373 (5)
N1—H1A	0.9000	C4—H4	0.9300
N1—H1B	0.9000	C5—C6	1.385 (5)
N2—C2	1.476 (5)	C5—H5	0.9300
N2—H2A	0.9000	C6—C7	1.406 (4)
N2—H2B	0.9000	C7—C8	1.354 (5)
N3—O2	1.223 (4)	C8—H8	0.9300
N3—O1	1.246 (4)
N1—Cu1—N1^i	180.00 (16)	O2—N3—O1	122.1 (3)
N1^i—Cu1—N2^i	84.46 (12)	O2—N3—C3	119.7 (3)
N1—Cu1—N2^i	95.54 (12)	O1—N3—C3	118.1 (3)
N1^i—Cu1—N2	95.54 (12)	C7—N4—S1	107.5 (2)
N1—Cu1—N2	84.46 (12)	C6—O3—S1	107.7 (2)
N1—Cu1—O1^i	85.89 (12)	N1—C1—C2	109.1 (3)
N2^i—Cu1—N2	180.00 (16)	N1—C1—H1C	109.9
N2—Cu1—O1^i	90.00 (11)	C2—C1—H1C	109.9
O1^i—Cu1—O1	180.00 (16)	N1—C1—H1D	109.9
O1—Cu1—N1	94.11 (12)	C2—C1—H1D	109.9
O1—Cu1—N1^i	85.89 (12)	H1C—C1—H1D	108.3
O1^i—Cu1—N1^i	94.11 (12)	N2—C2—C1	109.0 (3)
O1—Cu1—N2	90.00 (11)	N2—C2—H2C	109.9
O1—Cu1—N2^i	90.00 (11)	C1—C2—H2C	109.9
O1^i—Cu1—N2^i	90.00 (11)	N2—C2—H2D	109.9
O1—N3—O2	122.05 (17)	C1—C2—H2D	109.9
O1—N3—C3	118.11 (17)	H2C—C2—H2D	108.3
O4—S1—O5	115.20 (17)	C8—C3—C4	122.3 (3)
O4—S1—O3	113.57 (19)	C8—C3—N3	118.3 (3)
O5—S1—O3	113.39 (17)	C4—C3—N3	119.3 (3)
O4—S1—N4	107.06 (16)	C5—C4—C3	120.0 (3)
O5—S1—N4	106.49 (15)	C5—C4—H4	120.0
O3—S1—N4	99.36 (14)	C3—C4—H4	120.0
C1—N1—Cu1	108.1 (2)	C4—C5—C6	119.6 (3)
C1—N1—H1A	110.1	C4—C5—H5	120.2
Cu1—N1—H1A	110.1	C6—C5—H5	120.2
Cu1—O1—N3	127.6 (2)	O3—C6—C5	127.7 (3)
C1—N1—H1B	110.1	O3—C6—C7	114.2 (3)
Cu1—N1—H1B	110.1	C5—C6—C7	118.1 (3)
H1A—N1—H1B	108.4	C8—C7—N4	124.9 (3)
C2—N2—Cu1	110.3 (2)	C8—C7—C6	124.1 (3)
C2—N2—H2A	109.6	N4—C7—C6	111.0 (3)
Cu1—N2—H2A	109.6	C7—C8—C3	115.9 (3)
C2—N2—H2B	109.6	C7—C8—H8	122.1
Cu1—N2—H2B	109.6	C3—C8—H8	122.1
H2A—N2—H2B	108.1
O1^i—Cu1—N1—C1	70.8 (3)	O2—N3—C3—C8	−179.1 (4)
O1—N3—C3—C4	−178.9 (3)	O1—N3—C3—C8	−0.2 (5)
O1—Cu1—N1—C1	−109.2 (3)	O2—N3—C3—C4	2.1 (5)
O1^i—Cu1—N2—C2	−92.0 (3)	O2—N3—O1—Cu1	−37.8 (5)
O1—N3—C3—C8	−0.2 (4)	O1—N3—C3—C4	−179.0 (3)
O1—Cu1—N2—C2	88.0 (3)	C8—C3—C4—C5	2.2 (5)
N2^i—Cu1—N1—C1	160.4 (3)	N3—C3—C4—C5	−179.0 (3)
N2^i—Cu1—N1—C1	160.4 (3)	C3—C4—C5—C6	−0.5 (5)
N2—Cu1—N1—C1	−19.6 (3)	C3—N3—O1—Cu1	143.3 (2)
N2—Cu1—O1—N3	−49.0 (3)	S1—O3—C6—C5	−178.2 (3)
N2^i—Cu1—O1—N3	131.0 (3)	S1—O3—C6—C7	3.0 (4)
N1^i—Cu1—N2—C2	173.9 (3)	C4—C5—C6—O3	179.5 (3)
N1—Cu1—O1—N3	35.4 (3)	C4—C5—C6—C7	−1.7 (5)
N1—Cu1—N2—C2	−6.1 (3)	S1—N4—C7—C8	175.2 (3)
N1^i—Cu1—O1—N3	−144.6 (3)	S1—N4—C7—C6	−4.2 (3)
O4—S1—N4—C7	−112.9 (2)	O3—C6—C7—C8	−178.5 (3)
O5—S1—N4—C7	123.4 (2)	C5—C6—C7—C8	2.5 (5)
O3—S1—N4—C7	5.5 (3)	O3—C6—C7—N4	0.9 (4)
O4—S1—O3—C6	108.4 (2)	C5—C6—C7—N4	−178.0 (3)
O5—S1—O3—C6	−117.5 (2)	N4—C7—C8—C3	179.7 (3)
N4—S1—O3—C6	−4.9 (3)	C6—C7—C8—C3	−0.9 (5)
Cu1—N1—C1—C2	41.7 (4)	C4—C3—C8—C7	−1.5 (5)
Cu1—N2—C2—C1	30.4 (4)	N3—C3—C8—C7	179.7 (3)
N1—C1—C2—N2	−47.7 (5)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O5^ii	0.90	2.18	3.069 (4)	168
N1—H1A···O4^iii	0.90	2.38	2.993 (4)	125
N1—H1A···O2	0.90	2.55	3.265 (5)	136
N2—H2A···O3^iv	0.90	2.31	3.178 (4)	163
N2—H2B···O3^v	0.90	2.24	3.134 (4)	169

Symmetry codes: (ii) x−1, −y+1, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) x−1, y, z; (v) −x+1, y, −z+3/2.