Bis(4-amino­benzene­sulfonato-κN)bis­(N,N-dimethyl­formamide-κO)copper(II)

The Cu atom in the title zwitterionic complex, [Cu(C₆H₆N₂O₃S)₂(C₃H₇NO)₂], lies on a centre of inversion in a square plane formed by two N and two O atoms. Adjacent zwitterions are linked by a long Cu—O inter­action of 2.465 (2) Å to form a linear chain that runs along the b axis of the triclinic unit cell. The chain motif is consolidated by N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.134
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N1   -H1N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.850(10) ......       3.00 su-Ra
              N1   -H2N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(3), Rep   0.850(10) ......       3.00 su-Ra
              N1   -H2N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N1   -H1N     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.16(3), Rep   2.170(10) ......       3.00 su-Ra
              H2N  -O2      1.555   1.565

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

   5 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
   1 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

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(4-aminobenzenesulfonato-κN)bis(N,N-dimethylformamide-κO)copper(II)

Crystal data

[Cu(C6H6N2O3S)2(C3H7NO)2]	Z = 1
Mr = 554.09	F(000) = 287
Triclinic, P1	Dx = 1.655 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1168 (5) Å	Cell parameters from 3041 reflections
b = 8.4491 (6) Å	θ = 2.4–28.4°
c = 9.5294 (6) Å	µ = 1.22 mm^−1
α = 87.033 (1)°	T = 295 K
β = 77.344 (1)°	Plate, green
γ = 84.337 (1)°	0.20 × 0.16 × 0.04 mm
V = 556.09 (7) Å^3

Data collection

Bruker SMART APEX area-detector diffractometer	2426 independent reflections
Radiation source: fine-focus sealed tube	2246 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.797, Tmax = 0.953	k = −10→10
4574 measured reflections	l = −12→10

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0798P)^2 + 0.4598P] where P = (Fo^2 + 2Fc^2)/3
2426 reflections	(Δ/σ)max = 0.001
161 parameters	Δρmax = 0.43 e Å^−3
2 restraints	Δρmin = −0.40 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.5000	0.5000	0.0277 (2)
S1	0.8378 (1)	−0.25966 (7)	0.24513 (7)	0.0266 (2)
N1	0.7723 (3)	0.3882 (3)	0.4825 (3)	0.0272 (5)
N2	0.4769 (4)	0.7176 (3)	0.8822 (3)	0.0320 (5)
O1	0.6468 (3)	−0.3122 (3)	0.3104 (2)	0.0371 (5)
O2	0.9907 (3)	−0.3631 (3)	0.2932 (2)	0.0365 (5)
O3	0.8703 (4)	−0.2379 (3)	0.0908 (2)	0.0433 (6)
O4	0.5561 (3)	0.6234 (2)	0.6565 (2)	0.0318 (4)
C1	0.8380 (4)	−0.0694 (3)	0.3149 (3)	0.0253 (5)
C2	0.9140 (4)	0.0548 (3)	0.2277 (3)	0.0294 (6)
C3	0.8985 (4)	0.2059 (3)	0.2842 (3)	0.0296 (6)
C4	0.8081 (4)	0.2306 (3)	0.4261 (3)	0.0243 (5)
C5	0.7390 (4)	0.1042 (3)	0.5145 (3)	0.0298 (6)
C6	0.7533 (4)	−0.0457 (3)	0.4595 (3)	0.0292 (6)
C7	0.4648 (4)	0.6180 (4)	0.7852 (3)	0.0337 (6)
C8	0.5897 (6)	0.8538 (4)	0.8463 (4)	0.0466 (8)
C9	0.3571 (6)	0.7111 (5)	1.0269 (4)	0.0497 (9)
H1N	0.799 (6)	0.382 (5)	0.565 (2)	0.05 (1)*
H2N	0.840 (4)	0.456 (3)	0.429 (3)	0.03 (1)*
H2	0.9750	0.0379	0.1322	0.035*
H3	0.9492	0.2902	0.2262	0.036*
H5	0.6829	0.1203	0.6110	0.036*
H6	0.7065	−0.1305	0.5187	0.035*
H7	0.3830	0.5375	0.8132	0.040*
H8a	0.6849	0.8349	0.7590	0.070*
H8b	0.6532	0.8697	0.9229	0.070*
H8c	0.5058	0.9470	0.8332	0.070*
H9a	0.2873	0.6180	1.0390	0.075*
H9b	0.2671	0.8043	1.0413	0.075*
H9c	0.4377	0.7068	1.0959	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0323 (3)	0.0232 (3)	0.0297 (3)	0.0014 (2)	−0.0108 (2)	−0.0098 (2)
S1	0.0319 (4)	0.0217 (3)	0.0270 (4)	−0.0024 (3)	−0.0074 (3)	−0.0034 (2)
N1	0.032 (1)	0.022 (1)	0.030 (1)	−0.003 (1)	−0.010 (1)	−0.003 (1)
N2	0.036 (1)	0.034 (1)	0.027 (1)	−0.004 (1)	−0.005 (1)	−0.007 (1)
O1	0.035 (1)	0.031 (1)	0.048 (1)	−0.011 (1)	−0.009 (1)	−0.006 (1)
O2	0.038 (1)	0.030 (1)	0.043 (1)	0.001 (1)	−0.014 (1)	−0.002 (1)
O3	0.063 (2)	0.040 (1)	0.027 (1)	−0.006 (1)	−0.009 (1)	−0.005 (1)
O4	0.034 (1)	0.033 (1)	0.031 (1)	−0.001 (1)	−0.009 (1)	−0.012 (1)
C1	0.028 (1)	0.023 (1)	0.026 (1)	−0.003 (1)	−0.007 (1)	−0.001 (1)
C2	0.032 (1)	0.029 (1)	0.024 (1)	−0.001 (1)	0.000 (1)	−0.001 (1)
C3	0.032 (1)	0.022 (1)	0.032 (1)	−0.002 (1)	−0.001 (1)	0.003 (1)
C4	0.023 (1)	0.022 (1)	0.030 (1)	0.001 (1)	−0.009 (1)	−0.003 (1)
C5	0.035 (1)	0.032 (1)	0.022 (1)	−0.006 (1)	−0.004 (1)	−0.002 (1)
C6	0.037 (1)	0.022 (1)	0.028 (1)	−0.006 (1)	−0.004 (1)	0.001 (1)
C7	0.038 (2)	0.030 (1)	0.035 (2)	−0.006 (1)	−0.010 (1)	−0.004 (1)
C8	0.059 (2)	0.042 (2)	0.041 (2)	−0.018 (2)	−0.010 (2)	−0.011 (1)
C9	0.054 (2)	0.061 (2)	0.033 (2)	−0.008 (2)	−0.006 (2)	−0.005 (2)

Geometric parameters (Å, º)

Cu1—N1	2.047 (2)	C2—C3	1.396 (4)
Cu1—N1^i	2.047 (2)	C3—C4	1.381 (4)
Cu1—O1^ii	2.465 (2)	C4—C5	1.386 (4)
Cu1—O1^iii	2.465 (2)	C5—C6	1.382 (4)
Cu1—O4	1.994 (2)	N1—H1N	0.85 (1)
Cu1—O4^i	1.994 (2)	N1—H2N	0.85 (1)
S1—O3	1.443 (2)	C2—H2	0.93
S1—O2	1.465 (2)	C3—H3	0.93
S1—O1	1.467 (2)	C5—H5	0.93
S1—C1	1.771 (3)	C6—H6	0.93
N1—C4	1.440 (3)	C7—H7	0.93
N2—C7	1.304 (4)	C8—H8a	0.96
N2—C8	1.452 (4)	C8—H8b	0.96
N2—C9	1.455 (4)	C8—H8c	0.96
O4—C7	1.256 (4)	C9—H9a	0.96
C1—C2	1.382 (4)	C9—H9b	0.96
C1—C6	1.394 (4)	C9—H9c	0.96
O1^ii—Cu1—O1^iii	180	C5—C6—C1	119.7 (2)
O1^ii—Cu1—O4	92.87 (8)	O4—C7—N2	124.5 (3)
O1^ii—Cu1—O4^i	87.13 (8)	C4—N1—H1N	107 (3)
O1^ii—Cu1—N1	86.57 (9)	Cu1—N1—H1N	108 (3)
O1^ii—Cu1—N1^i	93.43 (8)	C4—N1—H2N	113 (2)
O4—Cu1—O4^i	180	Cu1—N1—H2N	101 (2)
O4—Cu1—N1	86.64 (9)	H1N—N1—H2N	110 (4)
O4—Cu1—N1^i	93.36 (9)	C1—C2—H2	120.3
N1—Cu1—N1^i	180	C3—C2—H2	120.3
O3—S1—O2	113.4 (2)	C4—C3—H3	119.9
O3—S1—O1	113.3 (2)	C2—C3—H3	119.9
O2—S1—O1	110.8 (1)	C6—C5—H5	119.9
O3—S1—C1	106.6 (1)	C4—C5—H5	119.9
O2—S1—C1	107.0 (1)	C5—C6—H6	120.1
O1—S1—C1	105.2 (1)	C1—C6—H6	120.1
C4—N1—Cu1	117.5 (2)	O4—C7—H7	117.7
C7—N2—C8	121.7 (3)	N2—C7—H7	117.7
C7—N2—C9	121.6 (3)	N2—C8—H8a	109.5
C8—N2—C9	116.2 (3)	N2—C8—H8b	109.5
C7—O4—Cu1	124.3 (2)	H8a—C8—H8b	109.5
C2—C1—C6	120.3 (2)	N2—C8—H8c	109.5
C2—C1—S1	121.2 (2)	H8a—C8—H8c	109.5
C6—C1—S1	118.4 (2)	H8b—C8—H8c	109.5
C1—C2—C3	119.4 (2)	N2—C9—H9a	109.5
C4—C3—C2	120.2 (2)	N2—C9—H9b	109.5
C3—C4—C5	120.1 (2)	H9a—C9—H9b	109.5
C3—C4—N1	121.1 (2)	N2—C9—H9c	109.5
C5—C4—N1	118.7 (2)	H9a—C9—H9c	109.5
C6—C5—C4	120.1 (3)	H9b—C9—H9c	109.5
O4^i—Cu1—N1—C4	−25.8 (2)	S1—C1—C2—C3	175.2 (2)
O4—Cu1—N1—C4	154.2 (2)	C1—C2—C3—C4	0.1 (4)
O1^iii—Cu1—N1—C4	67.3 (2)	C2—C3—C4—C5	2.5 (4)
O1^ii—Cu1—N1—C4	−112.7 (2)	C2—C3—C4—N1	−173.4 (3)
N1^i—Cu1—O4—C7	62.9 (2)	Cu1—N1—C4—C3	99.8 (3)
N1—Cu1—O4—C7	−117.1 (2)	Cu1—N1—C4—C5	−76.1 (3)
O1^iii—Cu1—O4—C7	−23.5 (2)	C3—C4—C5—C6	−2.6 (4)
O1^ii—Cu1—O4—C7	156.5 (2)	N1—C4—C5—C6	173.3 (3)
O3—S1—C1—C2	−17.0 (3)	C4—C5—C6—C1	0.2 (4)
O2—S1—C1—C2	104.6 (2)	C2—C1—C6—C5	2.4 (4)
O1—S1—C1—C2	−137.5 (2)	S1—C1—C6—C5	−175.4 (2)
O3—S1—C1—C6	160.8 (2)	Cu1—O4—C7—N2	−167.4 (2)
O2—S1—C1—C6	−77.6 (2)	C8—N2—C7—O4	4.5 (5)
O1—S1—C1—C6	40.3 (3)	C9—N2—C7—O4	175.7 (3)
C6—C1—C2—C3	−2.5 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N···O2^ii	0.85 (1)	2.17 (1)	3.018 (3)	176 (3)
N1—H1N···O2^iv	0.85 (1)	2.21 (2)	2.987 (3)	152 (4)

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