Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036811/hy2072sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036811/hy2072Isup2.hkl |
CCDC reference: 661673
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- R factor = 0.040
- wR factor = 0.106
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Cd1 (2) 3.59
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
An aqueous solution (5 ml) of Cd(ClO4)2.6H2O (0.422 g, 1.0 mmol) was added dropwise to a methanol solution (15 ml) of NaOH (0.041 g, 1.0 mmol), 5-bromosalicylaldehyde (0.202 g, 1.0 mmol) and aminomethanesulfonic acid (0.112 g, 1.0 mmol). The reaction mixture was refluxed for 4 h and added a methanol solution containing 1,10-phenanthroline (0.201 g, 1.0 mmol). The reaction mixture was refluxed for 6 h and then filtered. The resulting yellow filtrate was allowed to stand at room temperature for one month to afford yellow block-shaped crystals. Analysis, calculated for C21H18BrCdN3O5S: C 40.86, H 2.92, N 6.81%; found: C 39.96, H 2.84, N 6.87%.
All H atoms were positioned geometrically and refined as riding, with C—H = 0.93(CH), 0.97(CH2), 0.96(CH3) and 0.93 (OH) Å and Uiso(H)=1.5Ueq(C) for CH3 group and Uiso(H)=1.2Ueq(C, O) for the others.
During the last two decades, the Schiff base complexes containing sulfur and the complexes of amino acid Schiff bases have aroused increasing interest because of their antiviral, anticancer and antibacterial activities (Casella & Gullotti, 1981; Zhang et al., 2005). We have utilized aminomethanesulfonic acid and 5-bromosalicylaldehyde as ligands and investigated their reaction with cadmium acetate. We report here the structure of the title compound.
In the title compound, the CdII atom is six-coordinated by the imine N atom, the phenolate O atom and a sulfonate O atom from the tridentate Schiff base ligand, two N atoms from a phenanthroline ligand and one O atom from a methanol molecule. Thus the CdII atom has a distorted octahedral geometry (Fig. 1). The Cd—O distances are in a range of 1.977 (3)–2.381 (3) Å, and the mean Cd—O bond length is 2.198 (3) Å (Table 1). The Cd—N distances range from 2.084 (3) to 2.135 (3) Å. The Schiff base ligand adopts a κ3O,N,O'-tridentate mode, forming a five-membered ring and a six-membered ring. An O—H···O hydrogen bond between the coordinated O atom of the methanol molecule and an uncoordinated O atom of the sulfonate group and C—H···O hydrogen bonds are observed (Table 2).
For related literature, see: Casella & Gullotti (1981); Zhang et al. (2005).
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.
Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. |
[Cd(C8H6BrNO4S)(C12H8N2)(CH4O)] | F(000) = 1216 |
Mr = 616.76 | Dx = 1.913 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3340 reflections |
a = 18.712 (3) Å | θ = 2.2–25.9° |
b = 13.801 (1) Å | µ = 3.02 mm−1 |
c = 8.3681 (12) Å | T = 294 K |
β = 97.791 (2)° | Block, yellow |
V = 2141.1 (5) Å3 | 0.24 × 0.20 × 0.18 mm |
Z = 4 |
Bruker SMART 1000 CCD area-detector diffractometer | 4382 independent reflections |
Radiation source: fine-focus sealed tube | 2754 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
φ and ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −21→23 |
Tmin = 0.485, Tmax = 0.585 | k = −14→17 |
11883 measured reflections | l = −10→10 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0445P)2 + 0.319P] where P = (Fo2 + 2Fc2)/3 |
4382 reflections | (Δ/σ)max < 0.001 |
290 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.57 e Å−3 |
[Cd(C8H6BrNO4S)(C12H8N2)(CH4O)] | V = 2141.1 (5) Å3 |
Mr = 616.76 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.712 (3) Å | µ = 3.02 mm−1 |
b = 13.801 (1) Å | T = 294 K |
c = 8.3681 (12) Å | 0.24 × 0.20 × 0.18 mm |
β = 97.791 (2)° |
Bruker SMART 1000 CCD area-detector diffractometer | 4382 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2754 reflections with I > 2σ(I) |
Tmin = 0.485, Tmax = 0.585 | Rint = 0.061 |
11883 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.59 e Å−3 |
4382 reflections | Δρmin = −0.57 e Å−3 |
290 parameters |
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.26012 (2) | −0.00001 (3) | 1.04615 (6) | 0.03781 (15) | |
Br1 | −0.04473 (3) | 0.29929 (4) | 0.64972 (7) | 0.0725 (2) | |
S1 | 0.33001 (5) | 0.11933 (7) | 1.35725 (12) | 0.0389 (3) | |
O1 | 0.18426 (15) | 0.00142 (18) | 0.8572 (3) | 0.0473 (7) | |
O2 | 0.34653 (14) | 0.02965 (19) | 1.2771 (3) | 0.0441 (7) | |
O3 | 0.26898 (15) | 0.1068 (2) | 1.4462 (3) | 0.0499 (7) | |
O4 | 0.39171 (15) | 0.1656 (2) | 1.4478 (4) | 0.0572 (8) | |
N1 | 0.25062 (15) | 0.1493 (2) | 1.0740 (4) | 0.0331 (7) | |
N2 | 0.35398 (17) | −0.0178 (2) | 0.9297 (4) | 0.0373 (8) | |
N3 | 0.27402 (16) | −0.1520 (2) | 1.0582 (4) | 0.0344 (7) | |
C1 | 0.1391 (2) | 0.0703 (3) | 0.8111 (5) | 0.0371 (9) | |
C2 | 0.0840 (2) | 0.0536 (3) | 0.6811 (5) | 0.0465 (11) | |
H2 | 0.0835 | −0.0050 | 0.6263 | 0.056* | |
C3 | 0.0315 (2) | 0.1199 (3) | 0.6328 (5) | 0.0511 (12) | |
H3 | −0.0044 | 0.1054 | 0.5482 | 0.061* | |
C4 | 0.0316 (2) | 0.2091 (3) | 0.7097 (5) | 0.0451 (11) | |
C5 | 0.0855 (2) | 0.2317 (3) | 0.8304 (5) | 0.0387 (9) | |
H5 | 0.0863 | 0.2924 | 0.8789 | 0.046* | |
C6 | 0.14027 (19) | 0.1634 (3) | 0.8828 (4) | 0.0315 (8) | |
C7 | 0.19513 (19) | 0.1974 (3) | 1.0094 (4) | 0.0314 (8) | |
H7 | 0.1898 | 0.2599 | 1.0476 | 0.038* | |
C8 | 0.3014 (2) | 0.1992 (3) | 1.1928 (5) | 0.0398 (10) | |
H8A | 0.2786 | 0.2560 | 1.2319 | 0.048* | |
H8B | 0.3428 | 0.2204 | 1.1437 | 0.048* | |
C9 | 0.3917 (2) | 0.0482 (3) | 0.8632 (5) | 0.0504 (11) | |
H9 | 0.3771 | 0.1126 | 0.8647 | 0.060* | |
C10 | 0.4520 (2) | 0.0258 (3) | 0.7915 (6) | 0.0591 (13) | |
H10 | 0.4764 | 0.0744 | 0.7441 | 0.071* | |
C11 | 0.4754 (2) | −0.0664 (3) | 0.7904 (5) | 0.0532 (12) | |
H11 | 0.5165 | −0.0816 | 0.7440 | 0.064* | |
C12 | 0.4372 (2) | −0.1397 (3) | 0.8599 (5) | 0.0401 (10) | |
C13 | 0.4551 (2) | −0.2402 (3) | 0.8598 (5) | 0.0541 (12) | |
H13 | 0.4968 | −0.2593 | 0.8194 | 0.065* | |
C14 | 0.4137 (2) | −0.3080 (3) | 0.9160 (6) | 0.0533 (12) | |
H14 | 0.4266 | −0.3729 | 0.9116 | 0.064* | |
C15 | 0.3498 (2) | −0.2816 (3) | 0.9831 (5) | 0.0393 (10) | |
C16 | 0.3033 (3) | −0.3490 (3) | 1.0419 (5) | 0.0493 (11) | |
H16 | 0.3126 | −0.4150 | 1.0363 | 0.059* | |
C17 | 0.2447 (2) | −0.3174 (3) | 1.1070 (5) | 0.0502 (11) | |
H17 | 0.2138 | −0.3612 | 1.1470 | 0.060* | |
C18 | 0.2319 (2) | −0.2181 (3) | 1.1125 (5) | 0.0431 (10) | |
H18 | 0.1917 | −0.1970 | 1.1566 | 0.052* | |
C19 | 0.33226 (19) | −0.1828 (3) | 0.9920 (4) | 0.0323 (9) | |
C20 | 0.37606 (18) | −0.1110 (3) | 0.9276 (4) | 0.0317 (9) | |
O5 | 0.18771 (15) | −0.0173 (2) | 1.2362 (4) | 0.0511 (8) | |
H5A | 0.2086 | −0.0352 | 1.3391 | 0.061* | |
C21 | 0.1118 (3) | −0.0026 (4) | 1.2097 (7) | 0.0739 (16) | |
H21A | 0.1014 | 0.0585 | 1.1569 | 0.111* | |
H21B | 0.0933 | −0.0027 | 1.3112 | 0.111* | |
H21C | 0.0895 | −0.0538 | 1.1429 | 0.111* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.0392 (3) | 0.0302 (3) | 0.0458 (3) | 0.0055 (2) | 0.0122 (2) | −0.0006 (2) |
Br1 | 0.0512 (3) | 0.0899 (4) | 0.0723 (4) | 0.0222 (3) | −0.0059 (2) | 0.0143 (3) |
S1 | 0.0378 (5) | 0.0417 (6) | 0.0371 (6) | 0.0036 (5) | 0.0047 (4) | −0.0008 (5) |
O1 | 0.0520 (17) | 0.0361 (16) | 0.0517 (18) | 0.0076 (14) | −0.0011 (14) | −0.0076 (14) |
O2 | 0.0494 (16) | 0.0403 (16) | 0.0433 (16) | 0.0087 (13) | 0.0092 (13) | 0.0024 (13) |
O3 | 0.0525 (17) | 0.0535 (18) | 0.0477 (17) | 0.0026 (14) | 0.0211 (14) | −0.0016 (15) |
O4 | 0.0467 (17) | 0.069 (2) | 0.0511 (18) | −0.0030 (15) | −0.0094 (14) | −0.0088 (16) |
N1 | 0.0333 (17) | 0.0318 (17) | 0.0342 (18) | −0.0026 (14) | 0.0045 (14) | −0.0027 (14) |
N2 | 0.0396 (18) | 0.033 (2) | 0.0407 (19) | 0.0013 (15) | 0.0113 (15) | 0.0006 (15) |
N3 | 0.0377 (18) | 0.0308 (18) | 0.0347 (18) | 0.0003 (14) | 0.0052 (14) | 0.0009 (15) |
C1 | 0.042 (2) | 0.036 (2) | 0.034 (2) | −0.0053 (19) | 0.0087 (18) | 0.0001 (18) |
C2 | 0.060 (3) | 0.039 (3) | 0.039 (2) | −0.012 (2) | 0.001 (2) | −0.005 (2) |
C3 | 0.045 (3) | 0.062 (3) | 0.042 (3) | −0.018 (2) | −0.010 (2) | 0.008 (2) |
C4 | 0.035 (2) | 0.060 (3) | 0.040 (2) | 0.002 (2) | 0.0036 (18) | 0.010 (2) |
C5 | 0.040 (2) | 0.039 (2) | 0.039 (2) | 0.0059 (19) | 0.0098 (18) | −0.0005 (19) |
C6 | 0.0295 (19) | 0.035 (2) | 0.031 (2) | −0.0006 (17) | 0.0071 (16) | 0.0006 (17) |
C7 | 0.034 (2) | 0.028 (2) | 0.034 (2) | −0.0003 (17) | 0.0099 (16) | 0.0005 (17) |
C8 | 0.036 (2) | 0.037 (2) | 0.045 (2) | −0.0044 (18) | 0.0017 (18) | −0.0007 (19) |
C9 | 0.056 (3) | 0.037 (2) | 0.062 (3) | 0.000 (2) | 0.021 (2) | 0.003 (2) |
C10 | 0.058 (3) | 0.052 (3) | 0.073 (3) | −0.007 (2) | 0.030 (3) | 0.011 (3) |
C11 | 0.040 (2) | 0.064 (3) | 0.060 (3) | 0.002 (2) | 0.021 (2) | −0.007 (2) |
C12 | 0.035 (2) | 0.042 (2) | 0.043 (2) | 0.0046 (19) | 0.0033 (18) | −0.007 (2) |
C13 | 0.045 (3) | 0.059 (3) | 0.061 (3) | 0.016 (2) | 0.013 (2) | −0.006 (3) |
C14 | 0.059 (3) | 0.038 (3) | 0.062 (3) | 0.019 (2) | 0.006 (2) | −0.009 (2) |
C15 | 0.048 (2) | 0.031 (2) | 0.036 (2) | 0.0024 (19) | −0.0040 (19) | −0.0019 (18) |
C16 | 0.067 (3) | 0.032 (2) | 0.046 (3) | 0.001 (2) | −0.006 (2) | −0.002 (2) |
C17 | 0.061 (3) | 0.039 (3) | 0.049 (3) | −0.013 (2) | 0.003 (2) | 0.003 (2) |
C18 | 0.042 (2) | 0.044 (3) | 0.044 (2) | −0.0046 (19) | 0.0075 (19) | −0.001 (2) |
C19 | 0.031 (2) | 0.032 (2) | 0.033 (2) | 0.0038 (17) | −0.0017 (16) | −0.0037 (18) |
C20 | 0.033 (2) | 0.032 (2) | 0.030 (2) | 0.0031 (17) | 0.0009 (16) | −0.0044 (17) |
O5 | 0.0486 (17) | 0.0553 (19) | 0.0529 (18) | 0.0001 (14) | 0.0192 (14) | 0.0029 (15) |
C21 | 0.054 (3) | 0.098 (4) | 0.077 (4) | −0.009 (3) | 0.034 (3) | −0.012 (3) |
Cd1—O1 | 1.977 (3) | C7—H7 | 0.9300 |
Cd1—N1 | 2.084 (3) | C8—H8A | 0.9700 |
Cd1—N3 | 2.115 (3) | C8—H8B | 0.9700 |
Cd1—N2 | 2.135 (3) | C9—C10 | 1.383 (6) |
Cd1—O5 | 2.237 (3) | C9—H9 | 0.9300 |
Cd1—O2 | 2.381 (3) | C10—C11 | 1.347 (6) |
Br1—C4 | 1.910 (4) | C10—H10 | 0.9300 |
S1—O4 | 1.441 (3) | C11—C12 | 1.409 (6) |
S1—O3 | 1.455 (3) | C11—H11 | 0.9300 |
S1—O2 | 1.461 (3) | C12—C20 | 1.402 (5) |
S1—C8 | 1.788 (4) | C12—C13 | 1.427 (6) |
O1—C1 | 1.296 (4) | C13—C14 | 1.339 (6) |
N1—C7 | 1.288 (4) | C13—H13 | 0.9300 |
N1—C8 | 1.453 (4) | C14—C15 | 1.436 (6) |
N2—C9 | 1.321 (5) | C14—H14 | 0.9300 |
N2—C20 | 1.352 (4) | C15—C19 | 1.406 (5) |
N3—C18 | 1.324 (5) | C15—C16 | 1.407 (6) |
N3—C19 | 1.356 (5) | C16—C17 | 1.361 (6) |
C1—C2 | 1.412 (5) | C16—H16 | 0.9300 |
C1—C6 | 1.418 (5) | C17—C18 | 1.393 (5) |
C2—C3 | 1.362 (6) | C17—H17 | 0.9300 |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C3—C4 | 1.388 (6) | C19—C20 | 1.437 (5) |
C3—H3 | 0.9300 | O5—C21 | 1.422 (5) |
C4—C5 | 1.363 (5) | O5—H5A | 0.9300 |
C5—C6 | 1.417 (5) | C21—H21A | 0.9600 |
C5—H5 | 0.9300 | C21—H21B | 0.9600 |
C6—C7 | 1.449 (5) | C21—H21C | 0.9600 |
O1—Cd1—N1 | 90.95 (11) | C6—C7—H7 | 116.9 |
O1—Cd1—N3 | 96.80 (11) | N1—C8—S1 | 109.5 (2) |
N1—Cd1—N3 | 170.89 (11) | N1—C8—H8A | 109.8 |
O1—Cd1—N2 | 100.49 (12) | S1—C8—H8A | 109.8 |
N1—Cd1—N2 | 104.63 (12) | N1—C8—H8B | 109.8 |
N3—Cd1—N2 | 78.72 (12) | S1—C8—H8B | 109.8 |
O1—Cd1—O5 | 97.54 (12) | H8A—C8—H8B | 108.2 |
N1—Cd1—O5 | 87.53 (11) | N2—C9—C10 | 122.9 (4) |
N3—Cd1—O5 | 86.72 (11) | N2—C9—H9 | 118.6 |
N2—Cd1—O5 | 157.97 (11) | C10—C9—H9 | 118.6 |
O1—Cd1—O2 | 169.29 (10) | C11—C10—C9 | 120.0 (4) |
N1—Cd1—O2 | 78.36 (10) | C11—C10—H10 | 120.0 |
N3—Cd1—O2 | 93.80 (10) | C9—C10—H10 | 120.0 |
N2—Cd1—O2 | 83.10 (11) | C10—C11—C12 | 119.5 (4) |
O5—Cd1—O2 | 81.46 (10) | C10—C11—H11 | 120.3 |
O4—S1—O3 | 114.30 (18) | C12—C11—H11 | 120.3 |
O4—S1—O2 | 114.37 (17) | C20—C12—C11 | 116.8 (4) |
O3—S1—O2 | 111.35 (16) | C20—C12—C13 | 118.7 (4) |
O4—S1—C8 | 105.46 (18) | C11—C12—C13 | 124.4 (4) |
O3—S1—C8 | 107.03 (18) | C14—C13—C12 | 122.1 (4) |
O2—S1—C8 | 103.24 (17) | C14—C13—H13 | 118.9 |
C1—O1—Cd1 | 127.9 (2) | C12—C13—H13 | 118.9 |
S1—O2—Cd1 | 110.84 (14) | C13—C14—C15 | 120.8 (4) |
C7—N1—C8 | 117.2 (3) | C13—C14—H14 | 119.6 |
C7—N1—Cd1 | 122.6 (2) | C15—C14—H14 | 119.6 |
C8—N1—Cd1 | 119.2 (2) | C19—C15—C16 | 117.6 (4) |
C9—N2—C20 | 118.0 (3) | C19—C15—C14 | 118.6 (4) |
C9—N2—Cd1 | 129.3 (3) | C16—C15—C14 | 123.8 (4) |
C20—N2—Cd1 | 112.8 (2) | C17—C16—C15 | 119.9 (4) |
C18—N3—C19 | 118.2 (3) | C17—C16—H16 | 120.1 |
C18—N3—Cd1 | 128.6 (3) | C15—C16—H16 | 120.1 |
C19—N3—Cd1 | 113.1 (2) | C16—C17—C18 | 118.6 (4) |
O1—C1—C2 | 119.3 (4) | C16—C17—H17 | 120.7 |
O1—C1—C6 | 124.5 (3) | C18—C17—H17 | 120.7 |
C2—C1—C6 | 116.2 (4) | N3—C18—C17 | 123.6 (4) |
C3—C2—C1 | 122.7 (4) | N3—C18—H18 | 118.2 |
C3—C2—H2 | 118.6 | C17—C18—H18 | 118.2 |
C1—C2—H2 | 118.6 | N3—C19—C15 | 122.1 (4) |
C2—C3—C4 | 120.2 (4) | N3—C19—C20 | 117.9 (3) |
C2—C3—H3 | 119.9 | C15—C19—C20 | 120.0 (3) |
C4—C3—H3 | 119.9 | N2—C20—C12 | 122.9 (4) |
C5—C4—C3 | 120.0 (4) | N2—C20—C19 | 117.4 (3) |
C5—C4—Br1 | 119.8 (3) | C12—C20—C19 | 119.7 (3) |
C3—C4—Br1 | 120.1 (3) | C21—O5—Cd1 | 124.2 (3) |
C4—C5—C6 | 120.6 (4) | C21—O5—H5A | 117.9 |
C4—C5—H5 | 119.7 | Cd1—O5—H5A | 117.9 |
C6—C5—H5 | 119.7 | O5—C21—H21A | 109.5 |
C1—C6—C5 | 120.1 (3) | O5—C21—H21B | 109.5 |
C1—C6—C7 | 124.9 (3) | H21A—C21—H21B | 109.5 |
C5—C6—C7 | 115.0 (3) | O5—C21—H21C | 109.5 |
N1—C7—C6 | 126.2 (3) | H21A—C21—H21C | 109.5 |
N1—C7—H7 | 116.9 | H21B—C21—H21C | 109.5 |
N1—Cd1—O1—C1 | −14.3 (3) | C4—C5—C6—C7 | 178.6 (3) |
N3—Cd1—O1—C1 | 160.9 (3) | C8—N1—C7—C6 | 176.4 (3) |
N2—Cd1—O1—C1 | −119.4 (3) | Cd1—N1—C7—C6 | −14.8 (5) |
O5—Cd1—O1—C1 | 73.3 (3) | C1—C6—C7—N1 | 0.7 (6) |
O2—Cd1—O1—C1 | −10.6 (8) | C5—C6—C7—N1 | −178.7 (4) |
O4—S1—O2—Cd1 | −153.75 (17) | C7—N1—C8—S1 | 138.6 (3) |
O3—S1—O2—Cd1 | 74.79 (18) | Cd1—N1—C8—S1 | −30.6 (3) |
C8—S1—O2—Cd1 | −39.73 (19) | O4—S1—C8—N1 | 166.6 (3) |
O1—Cd1—O2—S1 | 19.0 (7) | O3—S1—C8—N1 | −71.3 (3) |
N1—Cd1—O2—S1 | 22.80 (16) | O2—S1—C8—N1 | 46.3 (3) |
N3—Cd1—O2—S1 | −152.52 (16) | C20—N2—C9—C10 | 0.4 (6) |
N2—Cd1—O2—S1 | 129.34 (17) | Cd1—N2—C9—C10 | 179.9 (3) |
O5—Cd1—O2—S1 | −66.42 (16) | N2—C9—C10—C11 | −1.3 (7) |
O1—Cd1—N1—C7 | 18.1 (3) | C9—C10—C11—C12 | 1.2 (7) |
N2—Cd1—N1—C7 | 119.2 (3) | C10—C11—C12—C20 | −0.1 (6) |
O5—Cd1—N1—C7 | −79.4 (3) | C10—C11—C12—C13 | 177.2 (4) |
O2—Cd1—N1—C7 | −161.2 (3) | C20—C12—C13—C14 | 2.8 (6) |
O1—Cd1—N1—C8 | −173.3 (3) | C11—C12—C13—C14 | −174.5 (4) |
N2—Cd1—N1—C8 | −72.2 (3) | C12—C13—C14—C15 | −1.5 (7) |
O5—Cd1—N1—C8 | 89.2 (3) | C13—C14—C15—C19 | −1.5 (6) |
O2—Cd1—N1—C8 | 7.4 (3) | C13—C14—C15—C16 | 179.0 (4) |
O1—Cd1—N2—C9 | 83.0 (4) | C19—C15—C16—C17 | −1.1 (6) |
N1—Cd1—N2—C9 | −10.7 (4) | C14—C15—C16—C17 | 178.5 (4) |
N3—Cd1—N2—C9 | 178.0 (4) | C15—C16—C17—C18 | 0.5 (6) |
O5—Cd1—N2—C9 | −132.5 (4) | C19—N3—C18—C17 | 0.8 (6) |
O2—Cd1—N2—C9 | −86.8 (4) | Cd1—N3—C18—C17 | 176.6 (3) |
O1—Cd1—N2—C20 | −97.4 (3) | C16—C17—C18—N3 | −0.3 (6) |
N1—Cd1—N2—C20 | 168.9 (2) | C18—N3—C19—C15 | −1.5 (5) |
N3—Cd1—N2—C20 | −2.4 (2) | Cd1—N3—C19—C15 | −177.9 (3) |
O5—Cd1—N2—C20 | 47.1 (4) | C18—N3—C19—C20 | 177.6 (3) |
O2—Cd1—N2—C20 | 92.9 (2) | Cd1—N3—C19—C20 | 1.1 (4) |
O1—Cd1—N3—C18 | −75.9 (3) | C16—C15—C19—N3 | 1.6 (5) |
N2—Cd1—N3—C18 | −175.3 (3) | C14—C15—C19—N3 | −178.0 (3) |
O5—Cd1—N3—C18 | 21.3 (3) | C16—C15—C19—C20 | −177.4 (3) |
O2—Cd1—N3—C18 | 102.5 (3) | C14—C15—C19—C20 | 3.0 (5) |
O1—Cd1—N3—C19 | 100.1 (2) | C9—N2—C20—C12 | 0.7 (5) |
N2—Cd1—N3—C19 | 0.7 (2) | Cd1—N2—C20—C12 | −178.9 (3) |
O5—Cd1—N3—C19 | −162.7 (2) | C9—N2—C20—C19 | −176.5 (3) |
O2—Cd1—N3—C19 | −81.5 (2) | Cd1—N2—C20—C19 | 3.8 (4) |
Cd1—O1—C1—C2 | −173.8 (3) | C11—C12—C20—N2 | −0.8 (5) |
Cd1—O1—C1—C6 | 6.0 (6) | C13—C12—C20—N2 | −178.4 (3) |
O1—C1—C2—C3 | 175.4 (4) | C11—C12—C20—C19 | 176.4 (3) |
C6—C1—C2—C3 | −4.4 (6) | C13—C12—C20—C19 | −1.2 (5) |
C1—C2—C3—C4 | 1.5 (7) | N3—C19—C20—N2 | −3.4 (5) |
C2—C3—C4—C5 | 2.0 (6) | C15—C19—C20—N2 | 175.7 (3) |
C2—C3—C4—Br1 | −176.6 (3) | N3—C19—C20—C12 | 179.2 (3) |
C3—C4—C5—C6 | −2.3 (6) | C15—C19—C20—C12 | −1.7 (5) |
Br1—C4—C5—C6 | 176.3 (3) | O1—Cd1—O5—C21 | −14.5 (3) |
O1—C1—C6—C5 | −175.8 (4) | N1—Cd1—O5—C21 | 76.2 (3) |
C2—C1—C6—C5 | 4.0 (5) | N3—Cd1—O5—C21 | −110.9 (3) |
O1—C1—C6—C7 | 4.8 (6) | N2—Cd1—O5—C21 | −159.3 (3) |
C2—C1—C6—C7 | −175.3 (3) | O2—Cd1—O5—C21 | 154.8 (3) |
C4—C5—C6—C1 | −0.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O3 | 0.93 | 2.38 | 2.759 (4) | 104 |
C7—H7···O3i | 0.93 | 2.58 | 3.113 (5) | 117 |
C8—H8B···O4i | 0.97 | 2.53 | 3.388 (5) | 147 |
C18—H18···O5 | 0.93 | 2.57 | 3.109 (5) | 117 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Cd(C8H6BrNO4S)(C12H8N2)(CH4O)] |
Mr | 616.76 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 18.712 (3), 13.801 (1), 8.3681 (12) |
β (°) | 97.791 (2) |
V (Å3) | 2141.1 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.02 |
Crystal size (mm) | 0.24 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.485, 0.585 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11883, 4382, 2754 |
Rint | 0.061 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.106, 1.03 |
No. of reflections | 4382 |
No. of parameters | 290 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.59, −0.57 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.
Cd1—O1 | 1.977 (3) | Cd1—N2 | 2.135 (3) |
Cd1—N1 | 2.084 (3) | Cd1—O5 | 2.237 (3) |
Cd1—N3 | 2.115 (3) | Cd1—O2 | 2.381 (3) |
O1—Cd1—N1 | 90.95 (11) | N3—Cd1—O5 | 86.72 (11) |
O1—Cd1—N3 | 96.80 (11) | N2—Cd1—O5 | 157.97 (11) |
N1—Cd1—N3 | 170.89 (11) | O1—Cd1—O2 | 169.29 (10) |
O1—Cd1—N2 | 100.49 (12) | N1—Cd1—O2 | 78.36 (10) |
N1—Cd1—N2 | 104.63 (12) | N3—Cd1—O2 | 93.80 (10) |
N3—Cd1—N2 | 78.72 (12) | N2—Cd1—O2 | 83.10 (11) |
O1—Cd1—O5 | 97.54 (12) | O5—Cd1—O2 | 81.46 (10) |
N1—Cd1—O5 | 87.53 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O3 | 0.93 | 2.38 | 2.759 (4) | 104 |
C7—H7···O3i | 0.93 | 2.58 | 3.113 (5) | 117 |
C8—H8B···O4i | 0.97 | 2.53 | 3.388 (5) | 147 |
C18—H18···O5 | 0.93 | 2.57 | 3.109 (5) | 117 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
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During the last two decades, the Schiff base complexes containing sulfur and the complexes of amino acid Schiff bases have aroused increasing interest because of their antiviral, anticancer and antibacterial activities (Casella & Gullotti, 1981; Zhang et al., 2005). We have utilized aminomethanesulfonic acid and 5-bromosalicylaldehyde as ligands and investigated their reaction with cadmium acetate. We report here the structure of the title compound.
In the title compound, the CdII atom is six-coordinated by the imine N atom, the phenolate O atom and a sulfonate O atom from the tridentate Schiff base ligand, two N atoms from a phenanthroline ligand and one O atom from a methanol molecule. Thus the CdII atom has a distorted octahedral geometry (Fig. 1). The Cd—O distances are in a range of 1.977 (3)–2.381 (3) Å, and the mean Cd—O bond length is 2.198 (3) Å (Table 1). The Cd—N distances range from 2.084 (3) to 2.135 (3) Å. The Schiff base ligand adopts a κ3O,N,O'-tridentate mode, forming a five-membered ring and a six-membered ring. An O—H···O hydrogen bond between the coordinated O atom of the methanol molecule and an uncoordinated O atom of the sulfonate group and C—H···O hydrogen bonds are observed (Table 2).