In the title compound, [Cu(C
6H
6NO
3S)
2(C
3H
7NO)
2(H
2O)
2], the Cu
II atom lies on an inversion centre and is six-coordinate, with a distorted octahedral coordination geometry. It is coordinated by the amine N atoms of two 4-aminobenzenesulfonate anions, the O atoms of two dimethylformamide molecules and two water molecules. Each pair of equivalent ligands is mutually
trans. N—H
O and O—H
O hydrogen-bonding interactions generate a three-dimensional architecture.
Supporting information
CCDC reference: 647345
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.002 Å
- R factor = 0.025
- wR factor = 0.074
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1 .. 6.25 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1W .. S1 .. 3.00 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2W .. S1 .. 3.00 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1
O1 -CU1 -O1 -C9 11.00 0.00 3.557 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 8
N1 -CU1 -N1 -C1 -69.00 12.00 3.557 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
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
5 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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, 2004); software used to prepare material for publication: SHELXTL.
Bis(4-aminobenzenesulfonato-
κN)diaquabis(
N,
N'-dimethylformamide-
κO)copper(II)
top
Crystal data top
[Cu(C6H6NO3S)2(C3H7NO)2(H2O)2] | F(000) = 614 |
Mr = 590.12 | Dx = 1.596 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5892 reflections |
a = 7.178 (1) Å | θ = 2.8–28.2° |
b = 11.8969 (16) Å | µ = 1.12 mm−1 |
c = 14.649 (2) Å | T = 291 K |
β = 100.973 (1)° | Block, blue |
V = 1228.1 (3) Å3 | 0.49 × 0.46 × 0.36 mm |
Z = 2 | |
Data collection top
Bruker APEXII CCD area-detector diffractometer | 2287 independent reflections |
Radiation source: fine-focus sealed tube | 2151 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
φ and ω scans | θmax = 25.5°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −8→8 |
Tmin = 0.610, Tmax = 0.689 | k = −14→14 |
7724 measured reflections | l = −17→13 |
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)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.074 | w = 1/[σ2(Fo2) + (0.0487P)2 + 0.4513P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
2287 reflections | Δρmax = 0.37 e Å−3 |
163 parameters | Δρmin = −0.41 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.079 (3) |
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 | 0.0000 | 0.0000 | 1.0000 | 0.02598 (14) | |
S1 | 0.00058 (5) | 0.20973 (3) | 0.54125 (3) | 0.02520 (15) | |
O1 | 0.20411 (17) | −0.03469 (11) | 1.10736 (8) | 0.0324 (3) | |
O2 | −0.00225 (18) | 0.19829 (11) | 1.03962 (10) | 0.0397 (3) | |
H1W | −0.1041 | 0.2304 | 1.0196 | 0.060* | |
H2W | 0.0891 | 0.2405 | 1.0347 | 0.060* | |
O3 | −0.00475 (18) | 0.33204 (10) | 0.55380 (9) | 0.0356 (3) | |
O4 | −0.18703 (17) | 0.16339 (11) | 0.50451 (9) | 0.0377 (3) | |
O5 | 0.1440 (2) | 0.17442 (12) | 0.48964 (9) | 0.0418 (3) | |
N1 | 0.21707 (19) | 0.02242 (11) | 0.92768 (10) | 0.0258 (3) | |
H1A | 0.3028 | 0.0689 | 0.9611 | 0.031* | |
H1B | 0.2746 | −0.0444 | 0.9251 | 0.031* | |
N2 | 0.3500 (2) | −0.02676 (14) | 1.25789 (11) | 0.0342 (3) | |
C1 | 0.1709 (2) | 0.06619 (13) | 0.83435 (11) | 0.0237 (3) | |
C2 | 0.1425 (2) | 0.18129 (13) | 0.82127 (11) | 0.0269 (3) | |
H2 | 0.1588 | 0.2293 | 0.8722 | 0.032* | |
C3 | 0.0900 (2) | 0.22408 (13) | 0.73200 (11) | 0.0256 (3) | |
H3 | 0.0699 | 0.3009 | 0.7234 | 0.031* | |
C4 | 0.0671 (2) | 0.15305 (13) | 0.65519 (11) | 0.0228 (3) | |
C5 | 0.0947 (2) | 0.03751 (14) | 0.66771 (11) | 0.0259 (3) | |
H5 | 0.0797 | −0.0104 | 0.6167 | 0.031* | |
C6 | 0.1452 (3) | −0.00535 (12) | 0.75778 (13) | 0.0269 (4) | |
H6 | 0.1618 | −0.0824 | 0.7667 | 0.032* | |
C7 | 0.4081 (3) | −0.14379 (18) | 1.25842 (15) | 0.0462 (5) | |
H7A | 0.3299 | −0.1880 | 1.2910 | 0.069* | |
H7B | 0.5384 | −0.1503 | 1.2890 | 0.069* | |
H7C | 0.3944 | −0.1704 | 1.1956 | 0.069* | |
C8 | 0.3890 (3) | 0.0345 (2) | 1.34637 (14) | 0.0517 (5) | |
H8A | 0.3290 | 0.1069 | 1.3385 | 0.078* | |
H8B | 0.5236 | 0.0440 | 1.3659 | 0.078* | |
H8C | 0.3401 | −0.0073 | 1.3927 | 0.078* | |
C9 | 0.2496 (2) | 0.01819 (15) | 1.18209 (13) | 0.0308 (4) | |
H9 | 0.2109 | 0.0926 | 1.1842 | 0.037* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.02576 (19) | 0.0340 (2) | 0.01685 (19) | 0.00005 (10) | 0.00076 (12) | 0.00382 (10) |
S1 | 0.0277 (2) | 0.0274 (2) | 0.0195 (2) | −0.00024 (14) | 0.00208 (16) | 0.00241 (15) |
O1 | 0.0307 (6) | 0.0421 (6) | 0.0226 (6) | 0.0019 (5) | 0.0002 (5) | 0.0039 (5) |
O2 | 0.0378 (7) | 0.0364 (7) | 0.0443 (8) | 0.0001 (5) | 0.0062 (6) | −0.0025 (6) |
O3 | 0.0463 (7) | 0.0270 (6) | 0.0306 (7) | 0.0003 (5) | 0.0003 (5) | 0.0045 (5) |
O4 | 0.0345 (7) | 0.0414 (7) | 0.0315 (7) | −0.0056 (5) | −0.0083 (5) | 0.0052 (6) |
O5 | 0.0488 (8) | 0.0503 (8) | 0.0302 (7) | 0.0029 (6) | 0.0176 (6) | 0.0016 (6) |
N1 | 0.0273 (7) | 0.0280 (6) | 0.0207 (7) | 0.0010 (5) | 0.0009 (6) | 0.0013 (5) |
N2 | 0.0294 (7) | 0.0490 (8) | 0.0227 (8) | −0.0024 (6) | 0.0009 (6) | 0.0052 (7) |
C1 | 0.0208 (7) | 0.0292 (8) | 0.0205 (8) | −0.0007 (6) | 0.0029 (6) | 0.0024 (6) |
C2 | 0.0324 (8) | 0.0275 (8) | 0.0202 (8) | −0.0018 (6) | 0.0037 (6) | −0.0045 (6) |
C3 | 0.0297 (8) | 0.0217 (7) | 0.0251 (8) | 0.0001 (6) | 0.0040 (6) | 0.0006 (6) |
C4 | 0.0201 (7) | 0.0274 (7) | 0.0202 (7) | 0.0002 (6) | 0.0024 (6) | 0.0007 (6) |
C5 | 0.0291 (8) | 0.0266 (8) | 0.0215 (8) | 0.0009 (6) | 0.0036 (6) | −0.0040 (6) |
C6 | 0.0304 (9) | 0.0231 (8) | 0.0266 (9) | 0.0030 (6) | 0.0040 (7) | 0.0006 (6) |
C7 | 0.0349 (9) | 0.0527 (11) | 0.0480 (12) | 0.0046 (8) | −0.0001 (9) | 0.0199 (10) |
C8 | 0.0476 (12) | 0.0794 (15) | 0.0259 (10) | −0.0128 (11) | 0.0011 (9) | −0.0043 (10) |
C9 | 0.0261 (8) | 0.0372 (9) | 0.0285 (9) | −0.0005 (7) | 0.0035 (7) | 0.0055 (7) |
Geometric parameters (Å, º) top
Cu1—O1i | 1.9781 (12) | N2—C8 | 1.467 (3) |
Cu1—O1 | 1.9781 (12) | C1—C2 | 1.392 (2) |
Cu1—N1i | 2.0615 (14) | C1—C6 | 1.392 (2) |
Cu1—N1 | 2.0615 (14) | C2—C3 | 1.387 (2) |
Cu1—O2i | 2.4301 (13) | C2—H2 | 0.9300 |
Cu1—O2 | 2.4301 (13) | C3—C4 | 1.392 (2) |
S1—O5 | 1.4509 (13) | C3—H3 | 0.9300 |
S1—O4 | 1.4598 (13) | C4—C5 | 1.396 (2) |
S1—O3 | 1.4680 (13) | C5—C6 | 1.396 (2) |
S1—C4 | 1.7791 (16) | C5—H5 | 0.9300 |
O1—C9 | 1.251 (2) | C6—H6 | 0.9300 |
O2—H1W | 0.8277 | C7—H7A | 0.9600 |
O2—H2W | 0.8402 | C7—H7B | 0.9600 |
N1—C1 | 1.441 (2) | C7—H7C | 0.9600 |
N1—H1A | 0.9000 | C8—H8A | 0.9600 |
N1—H1B | 0.9000 | C8—H8B | 0.9600 |
N2—C9 | 1.316 (2) | C8—H8C | 0.9600 |
N2—C7 | 1.453 (3) | C9—H9 | 0.9300 |
| | | |
O1i—Cu1—O1 | 180.00 (5) | C2—C1—C6 | 119.80 (14) |
O1i—Cu1—N1i | 85.28 (5) | C2—C1—N1 | 119.15 (14) |
O1—Cu1—N1i | 94.72 (5) | C6—C1—N1 | 120.97 (14) |
O1i—Cu1—N1 | 94.72 (5) | C3—C2—C1 | 119.81 (14) |
O1—Cu1—N1 | 85.28 (5) | C3—C2—H2 | 120.1 |
N1i—Cu1—N1 | 180.00 (4) | C1—C2—H2 | 120.1 |
O1i—Cu1—O2i | 92.88 (5) | C2—C3—C4 | 120.57 (14) |
O1—Cu1—O2i | 87.12 (5) | C2—C3—H3 | 119.7 |
N1i—Cu1—O2i | 92.14 (5) | C4—C3—H3 | 119.7 |
N1—Cu1—O2i | 87.87 (5) | C3—C4—C5 | 119.98 (14) |
O1i—Cu1—O2 | 87.12 (5) | C3—C4—S1 | 119.85 (12) |
O1—Cu1—O2 | 92.88 (5) | C5—C4—S1 | 120.17 (12) |
N1i—Cu1—O2 | 87.87 (5) | C6—C5—C4 | 119.25 (14) |
N1—Cu1—O2 | 92.13 (5) | C6—C5—H5 | 120.4 |
O2i—Cu1—O2 | 179.999 (1) | C4—C5—H5 | 120.4 |
O5—S1—O4 | 113.26 (8) | C5—C6—C1 | 120.58 (14) |
O5—S1—O3 | 112.97 (8) | C5—C6—H6 | 119.7 |
O4—S1—O3 | 112.10 (7) | C1—C6—H6 | 119.7 |
O5—S1—C4 | 106.78 (8) | N2—C7—H7A | 109.5 |
O4—S1—C4 | 105.47 (7) | N2—C7—H7B | 109.5 |
O3—S1—C4 | 105.49 (7) | H7A—C7—H7B | 109.5 |
C9—O1—Cu1 | 128.42 (12) | N2—C7—H7C | 109.5 |
Cu1—O2—H1W | 114.1 | H7A—C7—H7C | 109.5 |
Cu1—O2—H2W | 121.3 | H7B—C7—H7C | 109.5 |
H1W—O2—H2W | 110.2 | N2—C8—H8A | 109.5 |
C1—N1—Cu1 | 118.30 (10) | N2—C8—H8B | 109.5 |
C1—N1—H1A | 107.7 | H8A—C8—H8B | 109.5 |
Cu1—N1—H1A | 107.7 | N2—C8—H8C | 109.5 |
C1—N1—H1B | 107.7 | H8A—C8—H8C | 109.5 |
Cu1—N1—H1B | 107.7 | H8B—C8—H8C | 109.5 |
H1A—N1—H1B | 107.1 | O1—C9—N2 | 122.94 (17) |
C9—N2—C7 | 120.27 (17) | O1—C9—H9 | 118.5 |
C9—N2—C8 | 121.70 (18) | N2—C9—H9 | 118.5 |
C7—N2—C8 | 117.71 (17) | | |
| | | |
O1i—Cu1—O1—C9 | −114 (21) | C2—C3—C4—S1 | −179.75 (12) |
N1i—Cu1—O1—C9 | −64.29 (15) | O5—S1—C4—C3 | 124.23 (13) |
N1—Cu1—O1—C9 | 115.71 (15) | O4—S1—C4—C3 | −115.00 (13) |
O2i—Cu1—O1—C9 | −156.20 (15) | O3—S1—C4—C3 | 3.80 (14) |
O2—Cu1—O1—C9 | 23.80 (15) | O5—S1—C4—C5 | −56.33 (14) |
O1i—Cu1—N1—C1 | 7.27 (12) | O4—S1—C4—C5 | 64.44 (14) |
O1—Cu1—N1—C1 | −172.73 (12) | O3—S1—C4—C5 | −176.76 (12) |
N1i—Cu1—N1—C1 | −69 (12) | C3—C4—C5—C6 | 0.0 (2) |
O2i—Cu1—N1—C1 | 99.99 (11) | S1—C4—C5—C6 | −179.40 (12) |
O2—Cu1—N1—C1 | −80.01 (11) | C4—C5—C6—C1 | −1.1 (2) |
Cu1—N1—C1—C2 | 79.68 (16) | C2—C1—C6—C5 | 1.2 (2) |
Cu1—N1—C1—C6 | −97.15 (16) | N1—C1—C6—C5 | 178.03 (15) |
C6—C1—C2—C3 | −0.4 (2) | Cu1—O1—C9—N2 | 160.78 (13) |
N1—C1—C2—C3 | −177.24 (14) | C7—N2—C9—O1 | −2.0 (3) |
C1—C2—C3—C4 | −0.6 (2) | C8—N2—C9—O1 | −175.32 (17) |
C2—C3—C4—C5 | 0.8 (2) | | |
Symmetry code: (i) −x, −y, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1W···O5ii | 0.83 | 2.11 | 2.927 (2) | 171 |
O2—H1W···S1ii | 0.83 | 3.00 | 3.7372 (14) | 150 |
O2—H2W···O4iii | 0.84 | 2.09 | 2.9215 (19) | 172 |
O2—H2W···S1iii | 0.84 | 3.00 | 3.7672 (14) | 154 |
N1—H1A···O3iii | 0.90 | 2.10 | 2.9991 (19) | 173 |
N1—H1B···O3iv | 0.90 | 2.19 | 3.0421 (18) | 158 |
Symmetry codes: (ii) x−1/2, −y+1/2, z+1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+1/2, y−1/2, −z+3/2. |