The asymmetric unit of the title compound, [Cu(C
15H
10N
3O
4S)
2], contains one half-molecule. The other half of the complex molecule is related by a
C2 axis running through the Cu atom. The Cu atom is four-coordinated by two quinoline N and two sulfonamide N atoms. In the crystal structure, the molecules are linked through intermolecular C—H
O hydrogen bonds.
Supporting information
CCDC reference: 601117
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.006 Å
- R factor = 0.071
- wR factor = 0.202
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.108
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95
PLAT213_ALERT_2_C Atom O4 has ADP max/min Ratio ............. 3.10 prolat
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.61 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3
PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C1 .. 2.94 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 47.00 A 3
PLAT733_ALERT_1_C Torsion Calc -29.1(6), Rep -29.15(19) ...... 3.16 su-Rat
S1 -N1 -CU1 -N1 1.555 1.555 1.555 2.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4-PC (Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Bis[4-nitro-
N-(quinolin-8-yl)benzenesulfonamidato-
κ2N,
N']copper(II)
top
Crystal data top
[Cu(C15H10N3O4S)2] | F(000) = 1468 |
Mr = 720.18 | Dx = 1.567 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 14.101 (2) Å | θ = 4.1–22.8° |
b = 16.823 (2) Å | µ = 2.83 mm−1 |
c = 13.172 (2) Å | T = 299 K |
β = 102.35 (1)° | Prism, dark green |
V = 3052.4 (7) Å3 | 0.38 × 0.13 × 0.10 mm |
Z = 4 | |
Data collection top
Nonius CAD-4 diffractometer | 2074 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.108 |
Graphite monochromator | θmax = 67.0°, θmin = 4.2° |
ω/2θ scans | h = −16→16 |
Absorption correction: ψ scan (North et al., 1968) | k = −20→20 |
Tmin = 0.556, Tmax = 0.789 | l = −15→0 |
5582 measured reflections | 3 standard reflections every 120 min |
2720 independent reflections | intensity decay: 5.0% |
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)] = 0.071 | H-atom parameters constrained |
wR(F2) = 0.202 | w = 1/[σ2(Fo2) + (0.1447P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2720 reflections | Δρmax = 1.00 e Å−3 |
214 parameters | Δρmin = −1.58 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0019 (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 | |
C1 | −0.1090 (3) | 0.1940 (3) | 0.0526 (3) | 0.0414 (10) | |
H1 | −0.0538 | 0.2009 | 0.0257 | 0.050* | |
C2 | −0.1887 (3) | 0.1521 (3) | −0.0063 (3) | 0.0484 (11) | |
H2 | −0.1853 | 0.1308 | −0.0706 | 0.058* | |
C3 | −0.2708 (3) | 0.1432 (3) | 0.0316 (4) | 0.0494 (11) | |
H3 | −0.3239 | 0.1162 | −0.0073 | 0.059* | |
C4 | −0.2753 (3) | 0.1749 (3) | 0.1302 (3) | 0.0417 (10) | |
C5 | −0.3575 (3) | 0.1702 (3) | 0.1746 (4) | 0.0544 (13) | |
H5 | −0.4137 | 0.1453 | 0.1391 | 0.065* | |
C6 | −0.3539 (3) | 0.2024 (3) | 0.2695 (4) | 0.0571 (13) | |
H6 | −0.4085 | 0.1991 | 0.2984 | 0.069* | |
C7 | −0.2693 (3) | 0.2414 (3) | 0.3268 (4) | 0.0489 (11) | |
H7 | −0.2687 | 0.2620 | 0.3925 | 0.059* | |
C8 | −0.1891 (3) | 0.2483 (3) | 0.2849 (3) | 0.0362 (9) | |
C9 | −0.1919 (3) | 0.2146 (2) | 0.1849 (3) | 0.0347 (9) | |
C10 | 0.1791 (3) | 0.4300 (3) | 0.1814 (3) | 0.0394 (9) | |
C11 | 0.2698 (3) | 0.4416 (3) | 0.1585 (4) | 0.0505 (12) | |
H11 | 0.2841 | 0.4194 | 0.0989 | 0.061* | |
C12 | 0.3383 (3) | 0.4861 (3) | 0.2248 (4) | 0.0499 (11) | |
H12 | 0.3997 | 0.4937 | 0.2111 | 0.060* | |
C13 | 0.3146 (3) | 0.5192 (3) | 0.3112 (3) | 0.0416 (10) | |
C14 | 0.2231 (3) | 0.5109 (3) | 0.3339 (3) | 0.0432 (10) | |
H14 | 0.2080 | 0.5354 | 0.3917 | 0.052* | |
C15 | 0.1561 (3) | 0.4656 (3) | 0.2683 (3) | 0.0417 (10) | |
H15 | 0.0946 | 0.4586 | 0.2820 | 0.050* | |
N1 | 0.1000 (2) | 0.2856 (2) | 0.1714 (3) | 0.0408 (9) | |
N2 | −0.1109 (2) | 0.2236 (2) | 0.1449 (3) | 0.0349 (8) | |
N3 | 0.3895 (3) | 0.5633 (3) | 0.3854 (3) | 0.0596 (11) | |
O1 | −0.0010 (2) | 0.3956 (2) | 0.0945 (2) | 0.0516 (8) | |
O2 | 0.1304 (3) | 0.3520 (3) | 0.0085 (2) | 0.0623 (11) | |
O3 | 0.3707 (3) | 0.5931 (3) | 0.4612 (3) | 0.0790 (13) | |
O4 | 0.4684 (3) | 0.5684 (4) | 0.3643 (5) | 0.134 (3) | |
S1 | 0.09590 (7) | 0.36405 (7) | 0.10305 (7) | 0.0411 (4) | |
Cu1 | 0.0000 | 0.26765 (5) | 0.2500 | 0.0348 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.037 (2) | 0.049 (3) | 0.035 (2) | 0.0041 (18) | −0.0004 (16) | −0.0021 (17) |
C2 | 0.046 (2) | 0.052 (3) | 0.041 (2) | 0.005 (2) | −0.0054 (18) | −0.0085 (19) |
C3 | 0.041 (2) | 0.045 (2) | 0.052 (3) | −0.0028 (19) | −0.0132 (19) | −0.0022 (19) |
C4 | 0.030 (2) | 0.037 (2) | 0.051 (2) | −0.0032 (16) | −0.0057 (17) | 0.0101 (18) |
C5 | 0.033 (2) | 0.064 (3) | 0.062 (3) | −0.011 (2) | −0.002 (2) | 0.017 (2) |
C6 | 0.031 (2) | 0.072 (3) | 0.069 (3) | −0.009 (2) | 0.014 (2) | 0.019 (3) |
C7 | 0.035 (2) | 0.067 (3) | 0.046 (2) | −0.002 (2) | 0.0106 (18) | 0.010 (2) |
C8 | 0.0263 (18) | 0.044 (2) | 0.037 (2) | 0.0007 (15) | 0.0018 (15) | 0.0091 (16) |
C9 | 0.0269 (18) | 0.037 (2) | 0.036 (2) | 0.0000 (15) | −0.0031 (15) | 0.0098 (15) |
C10 | 0.033 (2) | 0.052 (3) | 0.0336 (19) | −0.0030 (18) | 0.0083 (15) | 0.0064 (17) |
C11 | 0.040 (2) | 0.073 (3) | 0.045 (2) | −0.005 (2) | 0.0235 (19) | −0.003 (2) |
C12 | 0.033 (2) | 0.058 (3) | 0.064 (3) | −0.0107 (19) | 0.024 (2) | −0.001 (2) |
C13 | 0.034 (2) | 0.046 (2) | 0.047 (2) | −0.0092 (17) | 0.0111 (17) | 0.0022 (18) |
C14 | 0.040 (2) | 0.054 (3) | 0.040 (2) | −0.0017 (19) | 0.0167 (17) | 0.0032 (19) |
C15 | 0.0291 (19) | 0.059 (3) | 0.039 (2) | 0.0001 (18) | 0.0128 (16) | 0.0052 (18) |
N1 | 0.0268 (16) | 0.061 (2) | 0.0326 (17) | −0.0007 (15) | 0.0019 (13) | 0.0002 (15) |
N2 | 0.0265 (15) | 0.0417 (19) | 0.0328 (16) | 0.0047 (13) | −0.0018 (12) | 0.0039 (14) |
N3 | 0.048 (2) | 0.070 (3) | 0.064 (3) | −0.022 (2) | 0.019 (2) | −0.015 (2) |
O1 | 0.0304 (15) | 0.073 (2) | 0.0479 (17) | 0.0039 (15) | 0.0018 (12) | 0.0142 (16) |
O2 | 0.062 (2) | 0.102 (3) | 0.0257 (15) | −0.010 (2) | 0.0153 (14) | −0.0020 (16) |
O3 | 0.073 (3) | 0.105 (4) | 0.061 (2) | −0.031 (3) | 0.020 (2) | −0.021 (2) |
O4 | 0.063 (3) | 0.181 (6) | 0.174 (5) | −0.069 (4) | 0.060 (3) | −0.115 (5) |
S1 | 0.0305 (6) | 0.0654 (8) | 0.0269 (5) | −0.0015 (4) | 0.0054 (4) | 0.0041 (4) |
Cu1 | 0.0212 (5) | 0.0528 (6) | 0.0285 (5) | 0.000 | 0.0012 (3) | 0.000 |
Geometric parameters (Å, º) top
C1—N2 | 1.319 (5) | C10—S1 | 1.776 (4) |
C1—C2 | 1.410 (6) | C11—C12 | 1.377 (7) |
C1—H1 | 0.9300 | C11—H11 | 0.9300 |
C2—C3 | 1.363 (7) | C12—C13 | 1.372 (6) |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
C3—C4 | 1.418 (7) | C13—C14 | 1.392 (5) |
C3—H3 | 0.9300 | C13—N3 | 1.476 (5) |
C4—C9 | 1.409 (5) | C14—C15 | 1.367 (6) |
C4—C5 | 1.409 (6) | C14—H14 | 0.9300 |
C5—C6 | 1.353 (7) | C15—H15 | 0.9300 |
C5—H5 | 0.9300 | N1—C8i | 1.413 (5) |
C6—C7 | 1.429 (7) | N1—S1 | 1.591 (4) |
C6—H6 | 0.9300 | N1—Cu1 | 1.943 (3) |
C7—C8 | 1.365 (6) | N2—Cu1 | 1.996 (3) |
C7—H7 | 0.9300 | N3—O3 | 1.198 (5) |
C8—N1i | 1.413 (5) | N3—O4 | 1.206 (6) |
C8—C9 | 1.427 (6) | O1—S1 | 1.448 (3) |
C9—N2 | 1.364 (5) | O2—S1 | 1.445 (3) |
C10—C11 | 1.389 (6) | Cu1—N1i | 1.943 (3) |
C10—C15 | 1.391 (6) | Cu1—N2i | 1.996 (3) |
| | | |
N2—C1—C2 | 121.7 (4) | C13—C12—C11 | 118.9 (4) |
N2—C1—H1 | 119.1 | C13—C12—H12 | 120.5 |
C2—C1—H1 | 119.1 | C11—C12—H12 | 120.5 |
C3—C2—C1 | 119.5 (4) | C12—C13—C14 | 122.6 (4) |
C3—C2—H2 | 120.2 | C12—C13—N3 | 119.1 (4) |
C1—C2—H2 | 120.2 | C14—C13—N3 | 118.3 (4) |
C2—C3—C4 | 120.1 (4) | C15—C14—C13 | 117.9 (4) |
C2—C3—H3 | 120.0 | C15—C14—H14 | 121.1 |
C4—C3—H3 | 120.0 | C13—C14—H14 | 121.1 |
C9—C4—C5 | 119.0 (4) | C14—C15—C10 | 120.5 (4) |
C9—C4—C3 | 116.8 (4) | C14—C15—H15 | 119.7 |
C5—C4—C3 | 124.1 (4) | C10—C15—H15 | 119.7 |
C6—C5—C4 | 119.3 (4) | C8i—N1—S1 | 121.4 (3) |
C6—C5—H5 | 120.3 | C8i—N1—Cu1 | 113.4 (3) |
C4—C5—H5 | 120.3 | S1—N1—Cu1 | 119.2 (2) |
C5—C6—C7 | 122.3 (4) | C1—N2—C9 | 119.8 (4) |
C5—C6—H6 | 118.9 | C1—N2—Cu1 | 127.8 (3) |
C7—C6—H6 | 118.9 | C9—N2—Cu1 | 111.7 (3) |
C8—C7—C6 | 119.7 (5) | O3—N3—O4 | 122.9 (5) |
C8—C7—H7 | 120.2 | O3—N3—C13 | 120.5 (4) |
C6—C7—H7 | 120.2 | O4—N3—C13 | 116.7 (4) |
C7—C8—N1i | 127.9 (4) | O2—S1—O1 | 118.0 (2) |
C7—C8—C9 | 118.6 (4) | O2—S1—N1 | 113.2 (2) |
N1i—C8—C9 | 113.5 (3) | O1—S1—N1 | 105.51 (19) |
N2—C9—C4 | 122.1 (4) | O2—S1—C10 | 106.6 (2) |
N2—C9—C8 | 116.9 (3) | O1—S1—C10 | 108.1 (2) |
C4—C9—C8 | 121.0 (4) | N1—S1—C10 | 104.47 (18) |
C11—C10—C15 | 120.4 (4) | N1—Cu1—N1i | 162.1 (2) |
C11—C10—S1 | 119.0 (3) | N1—Cu1—N2 | 103.79 (14) |
C15—C10—S1 | 120.4 (3) | N1i—Cu1—N2 | 82.95 (14) |
C12—C11—C10 | 119.5 (4) | N1—Cu1—N2i | 82.95 (14) |
C12—C11—H11 | 120.2 | N1i—Cu1—N2i | 103.79 (14) |
C10—C11—H11 | 120.2 | N2—Cu1—N2i | 136.37 (19) |
| | | |
N2—C1—C2—C3 | 1.4 (7) | C8—C9—N2—C1 | −179.8 (4) |
C1—C2—C3—C4 | −0.8 (7) | C4—C9—N2—Cu1 | −171.5 (3) |
C2—C3—C4—C9 | −0.4 (6) | C8—C9—N2—Cu1 | 9.3 (4) |
C2—C3—C4—C5 | 178.5 (5) | C12—C13—N3—O3 | 179.7 (5) |
C9—C4—C5—C6 | −1.3 (7) | C14—C13—N3—O3 | −2.2 (7) |
C3—C4—C5—C6 | 179.8 (5) | C12—C13—N3—O4 | 0.8 (8) |
C4—C5—C6—C7 | 0.1 (8) | C14—C13—N3—O4 | 178.9 (6) |
C5—C6—C7—C8 | 1.2 (8) | C8i—N1—S1—O2 | 63.5 (4) |
C6—C7—C8—N1i | 178.8 (4) | Cu1—N1—S1—O2 | −145.6 (2) |
C6—C7—C8—C9 | −1.2 (7) | C8i—N1—S1—O1 | −166.0 (3) |
C5—C4—C9—N2 | −177.8 (4) | Cu1—N1—S1—O1 | −15.1 (3) |
C3—C4—C9—N2 | 1.1 (6) | C8i—N1—S1—C10 | −52.1 (4) |
C5—C4—C9—C8 | 1.3 (6) | Cu1—N1—S1—C10 | 98.8 (2) |
C3—C4—C9—C8 | −179.7 (4) | C11—C10—S1—O2 | −16.9 (4) |
C7—C8—C9—N2 | 179.1 (4) | C15—C10—S1—O2 | 167.2 (4) |
N1i—C8—C9—N2 | −0.9 (5) | C11—C10—S1—O1 | −144.7 (4) |
C7—C8—C9—C4 | −0.1 (6) | C15—C10—S1—O1 | 39.4 (4) |
N1i—C8—C9—C4 | 179.9 (4) | C11—C10—S1—N1 | 103.2 (4) |
C15—C10—C11—C12 | 2.5 (7) | C15—C10—S1—N1 | −72.7 (4) |
S1—C10—C11—C12 | −173.4 (4) | C8i—N1—Cu1—N1i | 124.0 (3) |
C10—C11—C12—C13 | −1.0 (8) | S1—N1—Cu1—N1i | −29.15 (19) |
C11—C12—C13—C14 | −1.3 (7) | C8i—N1—Cu1—N2 | −125.6 (3) |
C11—C12—C13—N3 | 176.7 (5) | S1—N1—Cu1—N2 | 81.3 (2) |
C12—C13—C14—C15 | 2.2 (7) | C8i—N1—Cu1—N2i | 10.5 (3) |
N3—C13—C14—C15 | −175.8 (4) | S1—N1—Cu1—N2i | −142.6 (2) |
C13—C14—C15—C10 | −0.7 (7) | C1—N2—Cu1—N1 | 16.0 (4) |
C11—C10—C15—C14 | −1.6 (7) | C9—N2—Cu1—N1 | −173.9 (3) |
S1—C10—C15—C14 | 174.3 (4) | C1—N2—Cu1—N1i | 179.1 (4) |
C2—C1—N2—C9 | −0.7 (6) | C9—N2—Cu1—N1i | −10.8 (3) |
C2—C1—N2—Cu1 | 168.6 (3) | C1—N2—Cu1—N2i | −78.2 (4) |
C4—C9—N2—C1 | −0.6 (6) | C9—N2—Cu1—N2i | 91.8 (3) |
Symmetry code: (i) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1ii | 0.93 | 2.50 | 3.354 (5) | 153 |
C11—H11···O3iii | 0.93 | 2.40 | 3.271 (6) | 156 |
C15—H15···O1i | 0.93 | 2.54 | 3.335 (5) | 144 |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x−1/2, −y+1/2, −z; (iii) x, −y+1, z−1/2. |