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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810036135/zq2057sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810036135/zq2057Isup2.hkl |
CCDC reference: 754852
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.024
- wR factor = 0.065
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 3 PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety C9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To a solution of Ts-gly (1 mmol) in water-DMF 1:1 (10 ml), an aqueous solution (5 ml) of CuCl2.2H2O (1 mmol) and a solution of 1,10-phenanthroline (1 mmol) in ethanol (95%, 5 ml) was added. After refluxing for 12 h at 343 K, the mixture was filtered off while hot. The green single crystals suitable for a X-ray analysis were obtained by slow evaporation of the filtrate at room temperature after 41 days. IR(KBr): 3442(vs), 1638(vs), 1586(s), 1518(s), 1493(m), 1434(s), 1382(vs), 1348(m), 1319(m), 1243(vs), 1132(vs), 1112(vs), 1078(s), 1007(s), 967(s), 940(m), 847(s), 820(m), 723(s),663(s), 589(s), 545(m) cm-1.
H atoms bonded to C were placed geometrically and treated as riding with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C). The water H atoms were found in difference Fourier maps and refined with O—H = 0.85 Å and Uiso(H) = 1.5Ueq(O).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Cu(C9H9NO4S)(C12H8N2)(H2O)] | F(000) = 1004 |
Mr = 488.99 | Dx = 1.626 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.0788 (11) Å | Cell parameters from 7260 reflections |
b = 7.0588 (6) Å | θ = 2.8–28.2° |
c = 20.6993 (17) Å | µ = 1.24 mm−1 |
β = 103.826 (1)° | T = 296 K |
V = 1997.5 (3) Å3 | Block, green |
Z = 4 | 0.32 × 0.29 × 0.25 mm |
Bruker SMART CCD area-detector diffractometer | 3713 independent reflections |
Radiation source: fine-focus sealed tube | 3341 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ϕ and ω scans | θmax = 25.5°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −17→16 |
Tmin = 0.693, Tmax = 0.747 | k = −8→8 |
14609 measured reflections | l = −25→25 |
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)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.065 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0287P)2 + 1.2801P] where P = (Fo2 + 2Fc2)/3 |
3713 reflections | (Δ/σ)max = 0.001 |
281 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
[Cu(C9H9NO4S)(C12H8N2)(H2O)] | V = 1997.5 (3) Å3 |
Mr = 488.99 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.0788 (11) Å | µ = 1.24 mm−1 |
b = 7.0588 (6) Å | T = 296 K |
c = 20.6993 (17) Å | 0.32 × 0.29 × 0.25 mm |
β = 103.826 (1)° |
Bruker SMART CCD area-detector diffractometer | 3713 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 3341 reflections with I > 2σ(I) |
Tmin = 0.693, Tmax = 0.747 | Rint = 0.019 |
14609 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.065 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.27 e Å−3 |
3713 reflections | Δρmin = −0.30 e Å−3 |
281 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.245571 (16) | 0.54423 (3) | 0.471642 (10) | 0.02714 (8) | |
S1 | 0.24891 (3) | 0.25311 (7) | 0.34767 (2) | 0.02718 (12) | |
O1 | 0.35227 (10) | 0.4521 (2) | 0.54106 (6) | 0.0376 (3) | |
O2 | 0.49352 (10) | 0.2987 (2) | 0.55995 (7) | 0.0408 (4) | |
O3 | 0.14652 (10) | 0.3036 (2) | 0.32547 (7) | 0.0402 (4) | |
O4 | 0.26947 (12) | 0.0512 (2) | 0.34674 (7) | 0.0403 (4) | |
O5 | 0.32853 (10) | 0.8041 (2) | 0.45785 (8) | 0.0430 (4) | |
H1W | 0.3856 | 0.7738 | 0.4546 | 0.064* | |
H2W | 0.3065 | 0.8774 | 0.4251 | 0.064* | |
N1 | 0.29113 (11) | 0.3460 (2) | 0.41754 (7) | 0.0278 (4) | |
N2 | 0.17697 (11) | 0.6304 (2) | 0.54314 (7) | 0.0277 (3) | |
N3 | 0.12245 (11) | 0.6608 (2) | 0.41228 (7) | 0.0295 (4) | |
C1 | 0.41586 (13) | 0.3491 (3) | 0.52244 (9) | 0.0282 (4) | |
C2 | 0.39262 (13) | 0.2906 (3) | 0.45023 (9) | 0.0296 (4) | |
H2A | 0.4378 | 0.3513 | 0.4280 | 0.036* | |
H2B | 0.4000 | 0.1545 | 0.4470 | 0.036* | |
C3 | 0.30947 (13) | 0.3556 (3) | 0.28982 (9) | 0.0270 (4) | |
C4 | 0.32266 (16) | 0.2503 (3) | 0.23598 (10) | 0.0377 (5) | |
H4 | 0.3025 | 0.1246 | 0.2312 | 0.045* | |
C5 | 0.36591 (16) | 0.3329 (4) | 0.18939 (10) | 0.0428 (5) | |
H5A | 0.3745 | 0.2615 | 0.1534 | 0.051* | |
C6 | 0.39666 (15) | 0.5203 (3) | 0.19541 (10) | 0.0398 (5) | |
C7 | 0.38440 (16) | 0.6220 (3) | 0.25016 (11) | 0.0417 (5) | |
H7 | 0.4056 | 0.7471 | 0.2554 | 0.050* | |
C8 | 0.34130 (15) | 0.5416 (3) | 0.29733 (10) | 0.0354 (5) | |
H8 | 0.3339 | 0.6122 | 0.3337 | 0.042* | |
C9 | 0.4445 (2) | 0.6079 (5) | 0.14447 (13) | 0.0597 (7) | |
H9A | 0.4000 | 0.6037 | 0.1014 | 0.090* | |
H9B | 0.5027 | 0.5383 | 0.1433 | 0.090* | |
H9C | 0.4613 | 0.7372 | 0.1564 | 0.090* | |
C10 | 0.20889 (15) | 0.6202 (3) | 0.60898 (9) | 0.0345 (5) | |
H10 | 0.2727 | 0.5803 | 0.6270 | 0.041* | |
C11 | 0.14933 (17) | 0.6676 (3) | 0.65179 (10) | 0.0407 (5) | |
H11 | 0.1738 | 0.6595 | 0.6976 | 0.049* | |
C12 | 0.05523 (16) | 0.7258 (3) | 0.62636 (11) | 0.0376 (5) | |
H12 | 0.0151 | 0.7554 | 0.6547 | 0.045* | |
C13 | 0.01946 (14) | 0.7407 (3) | 0.55693 (10) | 0.0304 (4) | |
C14 | −0.07680 (15) | 0.8059 (3) | 0.52450 (11) | 0.0371 (5) | |
H14 | −0.1209 | 0.8361 | 0.5500 | 0.044* | |
C15 | −0.10434 (14) | 0.8240 (3) | 0.45780 (11) | 0.0373 (5) | |
H15 | −0.1672 | 0.8662 | 0.4381 | 0.045* | |
C16 | −0.03842 (14) | 0.7795 (3) | 0.41629 (10) | 0.0318 (4) | |
C17 | −0.05995 (16) | 0.8052 (3) | 0.34695 (11) | 0.0405 (5) | |
H17 | −0.1213 | 0.8484 | 0.3243 | 0.049* | |
C18 | 0.00994 (17) | 0.7661 (4) | 0.31331 (11) | 0.0449 (6) | |
H18 | −0.0027 | 0.7878 | 0.2677 | 0.054* | |
C19 | 0.10062 (16) | 0.6933 (3) | 0.34718 (10) | 0.0394 (5) | |
H19 | 0.1472 | 0.6667 | 0.3233 | 0.047* | |
C20 | 0.05477 (13) | 0.7091 (3) | 0.44656 (9) | 0.0265 (4) | |
C21 | 0.08421 (13) | 0.6912 (3) | 0.51756 (9) | 0.0255 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.02506 (13) | 0.03777 (15) | 0.01906 (12) | 0.00538 (10) | 0.00617 (9) | 0.00056 (9) |
S1 | 0.0249 (2) | 0.0364 (3) | 0.0212 (2) | −0.00450 (19) | 0.00735 (18) | −0.00286 (19) |
O1 | 0.0349 (8) | 0.0548 (10) | 0.0217 (7) | 0.0140 (7) | 0.0039 (6) | −0.0026 (6) |
O2 | 0.0281 (7) | 0.0573 (10) | 0.0331 (8) | 0.0079 (7) | 0.0001 (6) | 0.0035 (7) |
O3 | 0.0231 (7) | 0.0672 (11) | 0.0296 (7) | −0.0047 (7) | 0.0052 (6) | −0.0070 (7) |
O4 | 0.0549 (9) | 0.0337 (8) | 0.0325 (8) | −0.0083 (7) | 0.0112 (7) | −0.0030 (6) |
O5 | 0.0338 (8) | 0.0421 (9) | 0.0539 (10) | −0.0004 (7) | 0.0121 (7) | 0.0114 (7) |
N1 | 0.0222 (8) | 0.0404 (10) | 0.0206 (8) | 0.0022 (7) | 0.0048 (6) | −0.0032 (7) |
N2 | 0.0301 (8) | 0.0303 (9) | 0.0240 (8) | 0.0005 (7) | 0.0087 (6) | −0.0003 (7) |
N3 | 0.0291 (8) | 0.0365 (9) | 0.0230 (8) | 0.0037 (7) | 0.0068 (6) | 0.0020 (7) |
C1 | 0.0259 (10) | 0.0330 (11) | 0.0259 (9) | −0.0018 (8) | 0.0065 (8) | 0.0036 (8) |
C2 | 0.0245 (9) | 0.0353 (11) | 0.0291 (10) | 0.0014 (8) | 0.0066 (8) | −0.0037 (8) |
C3 | 0.0229 (9) | 0.0372 (11) | 0.0210 (9) | −0.0001 (8) | 0.0056 (7) | −0.0006 (8) |
C4 | 0.0428 (12) | 0.0423 (12) | 0.0310 (11) | −0.0082 (10) | 0.0146 (9) | −0.0100 (9) |
C5 | 0.0451 (13) | 0.0600 (15) | 0.0283 (11) | −0.0037 (11) | 0.0185 (9) | −0.0091 (10) |
C6 | 0.0317 (11) | 0.0587 (15) | 0.0313 (11) | −0.0005 (10) | 0.0120 (9) | 0.0079 (10) |
C7 | 0.0460 (13) | 0.0399 (12) | 0.0413 (12) | −0.0065 (10) | 0.0145 (10) | 0.0042 (10) |
C8 | 0.0403 (11) | 0.0390 (12) | 0.0296 (10) | −0.0014 (9) | 0.0134 (9) | −0.0039 (9) |
C9 | 0.0604 (16) | 0.0773 (19) | 0.0500 (15) | −0.0056 (14) | 0.0299 (13) | 0.0149 (14) |
C10 | 0.0370 (11) | 0.0415 (12) | 0.0248 (10) | 0.0012 (9) | 0.0071 (8) | −0.0007 (9) |
C11 | 0.0521 (13) | 0.0482 (13) | 0.0248 (10) | 0.0024 (11) | 0.0150 (9) | −0.0014 (9) |
C12 | 0.0460 (13) | 0.0381 (12) | 0.0365 (11) | −0.0029 (10) | 0.0252 (10) | −0.0042 (9) |
C13 | 0.0338 (10) | 0.0249 (10) | 0.0369 (11) | −0.0049 (8) | 0.0172 (9) | −0.0036 (8) |
C14 | 0.0315 (11) | 0.0321 (11) | 0.0542 (14) | −0.0019 (9) | 0.0233 (10) | −0.0034 (10) |
C15 | 0.0228 (10) | 0.0334 (11) | 0.0560 (14) | 0.0005 (8) | 0.0098 (9) | −0.0008 (10) |
C16 | 0.0266 (10) | 0.0263 (10) | 0.0406 (11) | −0.0018 (8) | 0.0044 (8) | −0.0014 (8) |
C17 | 0.0322 (11) | 0.0408 (12) | 0.0415 (12) | 0.0042 (9) | −0.0051 (9) | 0.0015 (10) |
C18 | 0.0475 (13) | 0.0553 (15) | 0.0266 (11) | 0.0079 (11) | −0.0017 (9) | 0.0049 (10) |
C19 | 0.0413 (12) | 0.0509 (13) | 0.0262 (10) | 0.0083 (10) | 0.0087 (9) | 0.0037 (9) |
C20 | 0.0263 (9) | 0.0237 (9) | 0.0299 (10) | −0.0018 (7) | 0.0075 (8) | −0.0010 (8) |
C21 | 0.0272 (9) | 0.0225 (9) | 0.0287 (9) | −0.0029 (7) | 0.0101 (8) | −0.0017 (7) |
Cu1—O1 | 1.9269 (13) | C6—C9 | 1.512 (3) |
Cu1—N1 | 1.9916 (16) | C7—C8 | 1.388 (3) |
Cu1—N3 | 2.0429 (16) | C7—H7 | 0.9300 |
Cu1—N2 | 2.0435 (15) | C8—H8 | 0.9300 |
Cu1—O5 | 2.2296 (15) | C9—H9A | 0.9600 |
S1—O3 | 1.4490 (14) | C9—H9B | 0.9600 |
S1—O4 | 1.4557 (16) | C9—H9C | 0.9600 |
S1—N1 | 1.5697 (15) | C10—C11 | 1.398 (3) |
S1—C3 | 1.7812 (19) | C10—H10 | 0.9300 |
O1—C1 | 1.282 (2) | C11—C12 | 1.367 (3) |
O2—C1 | 1.233 (2) | C11—H11 | 0.9300 |
O5—H1W | 0.8499 | C12—C13 | 1.409 (3) |
O5—H2W | 0.8500 | C12—H12 | 0.9300 |
N1—C2 | 1.480 (2) | C13—C21 | 1.404 (3) |
N2—C10 | 1.331 (2) | C13—C14 | 1.437 (3) |
N2—C21 | 1.356 (2) | C14—C15 | 1.348 (3) |
N3—C19 | 1.329 (2) | C14—H14 | 0.9300 |
N3—C20 | 1.360 (2) | C15—C16 | 1.442 (3) |
C1—C2 | 1.509 (3) | C15—H15 | 0.9300 |
C2—H2A | 0.9700 | C16—C20 | 1.403 (3) |
C2—H2B | 0.9700 | C16—C17 | 1.406 (3) |
C3—C8 | 1.384 (3) | C17—C18 | 1.363 (3) |
C3—C4 | 1.389 (3) | C17—H17 | 0.9300 |
C4—C5 | 1.386 (3) | C18—C19 | 1.399 (3) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.388 (3) | C19—H19 | 0.9300 |
C5—H5A | 0.9300 | C20—C21 | 1.434 (3) |
C6—C7 | 1.387 (3) | ||
O1—Cu1—N1 | 83.32 (6) | C5—C6—C9 | 120.5 (2) |
O1—Cu1—N3 | 169.34 (6) | C6—C7—C8 | 121.6 (2) |
N1—Cu1—N3 | 106.60 (6) | C6—C7—H7 | 119.2 |
O1—Cu1—N2 | 88.83 (6) | C8—C7—H7 | 119.2 |
N1—Cu1—N2 | 152.58 (7) | C3—C8—C7 | 119.55 (19) |
N3—Cu1—N2 | 80.56 (6) | C3—C8—H8 | 120.2 |
O1—Cu1—O5 | 91.97 (6) | C7—C8—H8 | 120.2 |
N1—Cu1—O5 | 104.91 (6) | C6—C9—H9A | 109.5 |
N3—Cu1—O5 | 89.24 (6) | C6—C9—H9B | 109.5 |
N2—Cu1—O5 | 101.57 (6) | H9A—C9—H9B | 109.5 |
O3—S1—O4 | 114.99 (9) | C6—C9—H9C | 109.5 |
O3—S1—N1 | 108.57 (8) | H9A—C9—H9C | 109.5 |
O4—S1—N1 | 112.86 (9) | H9B—C9—H9C | 109.5 |
O3—S1—C3 | 106.66 (9) | N2—C10—C11 | 121.93 (19) |
O4—S1—C3 | 105.09 (9) | N2—C10—H10 | 119.0 |
N1—S1—C3 | 108.24 (9) | C11—C10—H10 | 119.0 |
C1—O1—Cu1 | 116.31 (12) | C12—C11—C10 | 120.06 (19) |
Cu1—O5—H1W | 109.7 | C12—C11—H11 | 120.0 |
Cu1—O5—H2W | 120.0 | C10—C11—H11 | 120.0 |
H1W—O5—H2W | 105.2 | C11—C12—C13 | 119.51 (18) |
C2—N1—S1 | 114.99 (12) | C11—C12—H12 | 120.2 |
C2—N1—Cu1 | 109.52 (11) | C13—C12—H12 | 120.2 |
S1—N1—Cu1 | 135.20 (9) | C21—C13—C12 | 116.76 (18) |
C10—N2—C21 | 118.35 (16) | C21—C13—C14 | 118.63 (18) |
C10—N2—Cu1 | 128.54 (14) | C12—C13—C14 | 124.61 (18) |
C21—N2—Cu1 | 112.89 (12) | C15—C14—C13 | 121.15 (19) |
C19—N3—C20 | 117.69 (17) | C15—C14—H14 | 119.4 |
C19—N3—Cu1 | 129.57 (14) | C13—C14—H14 | 119.4 |
C20—N3—Cu1 | 112.74 (12) | C14—C15—C16 | 121.40 (19) |
O2—C1—O1 | 123.55 (18) | C14—C15—H15 | 119.3 |
O2—C1—C2 | 119.62 (17) | C16—C15—H15 | 119.3 |
O1—C1—C2 | 116.82 (16) | C20—C16—C17 | 116.87 (18) |
N1—C2—C1 | 109.72 (15) | C20—C16—C15 | 118.53 (19) |
N1—C2—H2A | 109.7 | C17—C16—C15 | 124.58 (19) |
C1—C2—H2A | 109.7 | C18—C17—C16 | 119.32 (19) |
N1—C2—H2B | 109.7 | C18—C17—H17 | 120.3 |
C1—C2—H2B | 109.7 | C16—C17—H17 | 120.3 |
H2A—C2—H2B | 108.2 | C17—C18—C19 | 120.1 (2) |
C8—C3—C4 | 119.75 (18) | C17—C18—H18 | 119.9 |
C8—C3—S1 | 120.27 (14) | C19—C18—H18 | 119.9 |
C4—C3—S1 | 119.96 (16) | N3—C19—C18 | 122.3 (2) |
C5—C4—C3 | 119.9 (2) | N3—C19—H19 | 118.9 |
C5—C4—H4 | 120.1 | C18—C19—H19 | 118.9 |
C3—C4—H4 | 120.1 | N3—C20—C16 | 123.56 (17) |
C4—C5—C6 | 121.2 (2) | N3—C20—C21 | 116.46 (16) |
C4—C5—H5A | 119.4 | C16—C20—C21 | 119.94 (17) |
C6—C5—H5A | 119.4 | N2—C21—C13 | 123.37 (17) |
C7—C6—C5 | 118.00 (19) | N2—C21—C20 | 116.33 (16) |
C7—C6—C9 | 121.4 (2) | C13—C21—C20 | 120.28 (17) |
N1—Cu1—O1—C1 | 15.55 (14) | S1—C3—C4—C5 | 177.14 (16) |
N3—Cu1—O1—C1 | 174.4 (3) | C3—C4—C5—C6 | 0.0 (3) |
N2—Cu1—O1—C1 | 169.23 (15) | C4—C5—C6—C7 | 1.1 (3) |
O5—Cu1—O1—C1 | −89.23 (15) | C4—C5—C6—C9 | 179.5 (2) |
O3—S1—N1—C2 | 173.74 (14) | C5—C6—C7—C8 | −1.1 (3) |
O4—S1—N1—C2 | 45.04 (16) | C9—C6—C7—C8 | −179.4 (2) |
C3—S1—N1—C2 | −70.84 (16) | C4—C3—C8—C7 | 1.3 (3) |
O3—S1—N1—Cu1 | −13.30 (17) | S1—C3—C8—C7 | −177.10 (16) |
O4—S1—N1—Cu1 | −142.00 (13) | C6—C7—C8—C3 | −0.1 (3) |
C3—S1—N1—Cu1 | 102.13 (14) | C21—N2—C10—C11 | 0.9 (3) |
O1—Cu1—N1—C2 | −18.70 (12) | Cu1—N2—C10—C11 | −173.35 (16) |
N3—Cu1—N1—C2 | 165.30 (12) | N2—C10—C11—C12 | 0.3 (3) |
N2—Cu1—N1—C2 | −93.00 (17) | C10—C11—C12—C13 | −1.1 (3) |
O5—Cu1—N1—C2 | 71.57 (13) | C11—C12—C13—C21 | 0.8 (3) |
O1—Cu1—N1—S1 | 168.06 (15) | C11—C12—C13—C14 | −177.9 (2) |
N3—Cu1—N1—S1 | −7.94 (16) | C21—C13—C14—C15 | −1.6 (3) |
N2—Cu1—N1—S1 | 93.76 (18) | C12—C13—C14—C15 | 177.1 (2) |
O5—Cu1—N1—S1 | −101.67 (14) | C13—C14—C15—C16 | −0.2 (3) |
O1—Cu1—N2—C10 | 2.40 (18) | C14—C15—C16—C20 | 2.4 (3) |
N1—Cu1—N2—C10 | 75.4 (2) | C14—C15—C16—C17 | −176.2 (2) |
N3—Cu1—N2—C10 | −176.63 (19) | C20—C16—C17—C18 | −1.6 (3) |
O5—Cu1—N2—C10 | −89.37 (18) | C15—C16—C17—C18 | 177.0 (2) |
O1—Cu1—N2—C21 | −172.10 (14) | C16—C17—C18—C19 | 2.8 (4) |
N1—Cu1—N2—C21 | −99.09 (17) | C20—N3—C19—C18 | −3.0 (3) |
N3—Cu1—N2—C21 | 8.87 (13) | Cu1—N3—C19—C18 | 176.61 (17) |
O5—Cu1—N2—C21 | 96.13 (13) | C17—C18—C19—N3 | −0.4 (4) |
O1—Cu1—N3—C19 | 166.8 (3) | C19—N3—C20—C16 | 4.2 (3) |
N1—Cu1—N3—C19 | −35.2 (2) | Cu1—N3—C20—C16 | −175.48 (15) |
N2—Cu1—N3—C19 | 172.0 (2) | C19—N3—C20—C21 | −173.60 (18) |
O5—Cu1—N3—C19 | 70.10 (19) | Cu1—N3—C20—C21 | 6.7 (2) |
O1—Cu1—N3—C20 | −13.6 (4) | C17—C16—C20—N3 | −1.9 (3) |
N1—Cu1—N3—C20 | 144.41 (13) | C15—C16—C20—N3 | 179.39 (18) |
N2—Cu1—N3—C20 | −8.39 (13) | C17—C16—C20—C21 | 175.84 (18) |
O5—Cu1—N3—C20 | −110.25 (13) | C15—C16—C20—C21 | −2.9 (3) |
Cu1—O1—C1—O2 | 171.25 (16) | C10—N2—C21—C13 | −1.2 (3) |
Cu1—O1—C1—C2 | −8.1 (2) | Cu1—N2—C21—C13 | 173.90 (14) |
S1—N1—C2—C1 | −166.30 (13) | C10—N2—C21—C20 | 176.91 (17) |
Cu1—N1—C2—C1 | 18.95 (19) | Cu1—N2—C21—C20 | −8.0 (2) |
O2—C1—C2—N1 | 172.71 (18) | C12—C13—C21—N2 | 0.4 (3) |
O1—C1—C2—N1 | −7.9 (2) | C14—C13—C21—N2 | 179.15 (18) |
O3—S1—C3—C8 | 85.06 (17) | C12—C13—C21—C20 | −177.67 (18) |
O4—S1—C3—C8 | −152.43 (16) | C14—C13—C21—C20 | 1.1 (3) |
N1—S1—C3—C8 | −31.60 (19) | N3—C20—C21—N2 | 0.9 (3) |
O3—S1—C3—C4 | −93.29 (18) | C16—C20—C21—N2 | −177.04 (17) |
O4—S1—C3—C4 | 29.22 (19) | N3—C20—C21—C13 | 179.05 (17) |
N1—S1—C3—C4 | 150.05 (16) | C16—C20—C21—C13 | 1.2 (3) |
C8—C3—C4—C5 | −1.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H1W···O2i | 0.85 | 1.87 | 2.717 (2) | 175 |
O5—H2W···O4ii | 0.85 | 2.00 | 2.847 (2) | 174 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C9H9NO4S)(C12H8N2)(H2O)] |
Mr | 488.99 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 14.0788 (11), 7.0588 (6), 20.6993 (17) |
β (°) | 103.826 (1) |
V (Å3) | 1997.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.24 |
Crystal size (mm) | 0.32 × 0.29 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.693, 0.747 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14609, 3713, 3341 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.065, 1.06 |
No. of reflections | 3713 |
No. of parameters | 281 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.30 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H1W···O2i | 0.85 | 1.87 | 2.717 (2) | 175.2 |
O5—H2W···O4ii | 0.85 | 2.00 | 2.847 (2) | 173.7 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z. |
As a kind of amino acid derivatives, the N-protected amino acid plays an important role in participating in the process of the life activity. The substitution of an Ar—SO2-group on the amine nitrogen of amino acids, such as glycine and B-alanine, increases the coordination donors behavior of amino acids to three types of O, N donors from carboxyl, sulfoxyl and amine respectively, which may lead to different coordination modes, thus is of great interest in studying the coordination chemistry of N-sulfonyl- amino acids for many chemical workers (Ma et al., 2008; Liang et al., 2004; Battaglia et al., 1983; Menabue et al., 1991; Antolini et al., 1985). In order to continue the research, we synthesized the title complex [Cu(C9H9NO4S)(C12H8N2)(H2O)] and characterized it by an elemental analysis and a single-crystal X-ray diffraction analysis.
The molecular structure and crystal packing diagram of the title compound are presented in Figs. 1 and 2, respectively. The asymmetric unit contains one copper cation, one Ts-gly anion, one phen molecule and one coordinated water molecule. The central copper ion adopts a distorted square-pyramidal geometry by two N(N2, N3) atoms of the 1,10-phenanthroline ligand, one N(N1) and one O(O1) atoms of the Ts-gly ion occupying basal site, while the apical position is occupied by another O atom of a water molecule. The Cu—O1 bond distance of 1.9269 (13) Å is shorter than those of other N-protected glycine complexes (1.933–1.967 Å) [Battaglia, et al., 1983; Antolini, et al., 1985; Menabue & Saladini, 1991]. Furthermore, the C—O bond distance for the coordinated O atom (1.282 (2) Å) is significantly longer than that for the uncoordinated O atom (1.233 (2) Å), which is similar to previously reported complexes (Battaglia, et al., 1983; Antolini, et al., 1985).
Intermolecular hydrogen bonds involving the water H atoms, O(5)—H(1W)···O(2)i, O(5)—H(2W)···O(4)ii (Table 1), link the neighboring molecules into one-dimensional supramolecular chains. Weak π-π stacking interactions between benzene rings of 1,10-phenanthroline ligands from adjacent molecules (centroid distances of 3.456Å and 3.691 Å) extend the one-dimensional chains into a two-dimensional layer structure.