Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029673/dn6244sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029673/dn6244Isup2.hkl |
CCDC reference: 257361
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.115
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Zn1 - O42 .. 15.46 su PLAT420_ALERT_2_B D-H Without Acceptor O9 - H50 ... ?
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C43 PLAT420_ALERT_2_C D-H Without Acceptor N6 - H6A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N40 - H40A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N42 - H42D ... ?
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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
All reagents were purchased from commercial sources and used as supplied. An ethanol solution (20 ml) of 2-sulfanilamidopyrimidin (H—SD; 2 mmol) was added dropwise to a stirred solution of ZnII acetate (1 mmol) in distilled water (30 ml). A brown precipitate began to form and the reaction mixture was stirred overnight at 313 K. The products were isolated by filtration, washed with cold distilled water and ether, and dried in air. The 2-sulfanilamidopyrimidin–ethylenediamine (en) mixed-ligand complex was prepared as follows. A solution of en (2 mmol) in ethanol (30 ml) was added dropwise with stirring to a solution of [Zn(SD)2] (1 mmol) dissolved in ethanol (50 ml) and stirred for 4 h at 323 K in a temperature-controlled bath. A dark-violet polycrystalline precipitate was filtered off and crystals of (I) suitable for X-ray diffraction were co-crystallized as violet [Blue below?] crystals by slow diffusion of Et2O into the filtrate. Analysis, calculated: C 39.14, H 5.43, N 22.83%; found: C 39.10, H 5.45, N 22.87%.
Water H atoms were located in a difference Fourier map and refined using distance restraints of O—H = 0.85 Å and H···H = 1.39 Å, with Uiso(H) = 1.5Ueq(O). All other H atoms were placed in idealized positions and constrained to ride on their parent atoms (C or N), with C—H and N—H distances in the range 0.85–0.93 Å, and with Uiso(H) = 1.2Ueq(C,N).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).
[Zn(C4H8N4)(H2O)2](C10H9N4O2S)2·H2O | F(000) = 1544 |
Mr = 738.17 | Dx = 1.532 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 28720 reflections |
a = 13.7400 (5) Å | θ = 1.3–26.7° |
b = 14.6581 (7) Å | µ = 0.96 mm−1 |
c = 15.9408 (6) Å | T = 293 K |
β = 94.510 (3)° | Prism, blue |
V = 3200.6 (2) Å3 | 0.38 × 0.33 × 0.22 mm |
Z = 4 |
Stoe IPDS 2 diffractometer | 6655 independent reflections |
Radiation source: fine-focus sealed tube | 4864 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.6°, θmin = 1.5° |
ϕ scans | h = −17→17 |
Absorption correction: integration X-RED32 (Stoe & Cie, 2002) | k = −18→18 |
Tmin = 0.749, Tmax = 0.829 | l = −19→19 |
32597 measured reflections |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0765P)2] where P = (Fo2 + 2Fc2)/3 |
6655 reflections | (Δ/σ)max = 0.009 |
433 parameters | Δρmax = 0.41 e Å−3 |
9 restraints | Δρmin = −0.57 e Å−3 |
[Zn(C4H8N4)(H2O)2](C10H9N4O2S)2·H2O | V = 3200.6 (2) Å3 |
Mr = 738.17 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.7400 (5) Å | µ = 0.96 mm−1 |
b = 14.6581 (7) Å | T = 293 K |
c = 15.9408 (6) Å | 0.38 × 0.33 × 0.22 mm |
β = 94.510 (3)° |
Stoe IPDS 2 diffractometer | 6655 independent reflections |
Absorption correction: integration X-RED32 (Stoe & Cie, 2002) | 4864 reflections with I > 2σ(I) |
Tmin = 0.749, Tmax = 0.829 | Rint = 0.062 |
32597 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 9 restraints |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.41 e Å−3 |
6655 reflections | Δρmin = −0.57 e Å−3 |
433 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 | ||
C1 | −0.06781 (18) | 0.67120 (19) | 0.02078 (15) | 0.0434 (6) | |
C3 | −0.0219 (2) | 0.5794 (2) | −0.08450 (18) | 0.0495 (6) | |
H3 | −0.0377 | 0.5448 | −0.1326 | 0.059* | |
C4 | 0.0736 (2) | 0.5826 (2) | −0.05319 (19) | 0.0530 (7) | |
H4 | 0.1225 | 0.5515 | −0.0786 | 0.064* | |
C5 | 0.0932 (2) | 0.6343 (2) | 0.01778 (18) | 0.0509 (7) | |
H5 | 0.1574 | 0.6379 | 0.0407 | 0.061* | |
C7 | −0.07516 (19) | 0.70420 (18) | 0.21996 (16) | 0.0429 (6) | |
C8 | −0.0978 (2) | 0.61266 (19) | 0.22561 (17) | 0.0479 (6) | |
H8 | −0.1385 | 0.5855 | 0.1834 | 0.058* | |
C9 | −0.0608 (2) | 0.5615 (2) | 0.29293 (18) | 0.0516 (7) | |
H9 | −0.0760 | 0.4997 | 0.2957 | 0.062* | |
C10 | −0.0002 (2) | 0.60188 (19) | 0.35775 (16) | 0.0479 (6) | |
C11 | 0.0230 (2) | 0.6941 (2) | 0.35057 (16) | 0.0489 (6) | |
H11 | 0.0638 | 0.7218 | 0.3924 | 0.059* | |
C12 | −0.0137 (2) | 0.74465 (18) | 0.28235 (17) | 0.0461 (6) | |
H12 | 0.0027 | 0.8059 | 0.2782 | 0.055* | |
C13 | 0.2870 (2) | 0.8081 (2) | 0.38045 (17) | 0.0501 (6) | |
H13 | 0.2505 | 0.7794 | 0.3364 | 0.060* | |
C14 | 0.3139 (2) | 0.75970 (19) | 0.45267 (17) | 0.0469 (6) | |
H14 | 0.2949 | 0.6991 | 0.4573 | 0.056* | |
C15 | 0.36937 (18) | 0.80103 (18) | 0.51857 (15) | 0.0407 (5) | |
C16 | 0.3947 (2) | 0.89199 (18) | 0.51204 (16) | 0.0465 (6) | |
H16 | 0.4312 | 0.9202 | 0.5563 | 0.056* | |
C17 | 0.3663 (2) | 0.94113 (19) | 0.44062 (17) | 0.0495 (6) | |
H17 | 0.3823 | 1.0026 | 0.4376 | 0.059* | |
C18 | 0.3134 (2) | 0.8991 (2) | 0.37236 (16) | 0.0488 (6) | |
C21 | 0.36073 (18) | 0.84593 (17) | 0.72034 (14) | 0.0393 (5) | |
C23 | 0.3214 (2) | 0.9402 (2) | 0.82563 (17) | 0.0546 (7) | |
H23 | 0.3398 | 0.9745 | 0.8734 | 0.066* | |
C24 | 0.2250 (2) | 0.9402 (2) | 0.79683 (19) | 0.0577 (7) | |
H24 | 0.1784 | 0.9737 | 0.8228 | 0.069* | |
C25 | 0.2015 (2) | 0.8872 (2) | 0.72681 (18) | 0.0506 (6) | |
H25 | 0.1363 | 0.8837 | 0.7062 | 0.061* | |
C41 | 0.3382 (2) | 0.4158 (2) | 0.15489 (19) | 0.0560 (7) | |
H41A | 0.3098 | 0.4676 | 0.1820 | 0.067* | |
H41B | 0.3468 | 0.4320 | 0.0969 | 0.067* | |
C42 | 0.4343 (2) | 0.3914 (2) | 0.1997 (2) | 0.0561 (7) | |
H42A | 0.4812 | 0.4399 | 0.1934 | 0.067* | |
H42B | 0.4271 | 0.3827 | 0.2592 | 0.067* | |
C43 | 0.2744 (3) | 0.0709 (2) | 0.0375 (3) | 0.0807 (11) | |
H43A | 0.2302 | 0.0197 | 0.0406 | 0.097* | |
H43B | 0.2767 | 0.0874 | −0.0213 | 0.097* | |
C44 | 0.3721 (3) | 0.0445 (2) | 0.0725 (2) | 0.0719 (9) | |
H44A | 0.3676 | 0.0139 | 0.1260 | 0.086* | |
H44B | 0.4010 | 0.0026 | 0.0345 | 0.086* | |
Zn1 | 0.35190 (2) | 0.22955 (2) | 0.122342 (18) | 0.04256 (11) | |
N1 | −0.14466 (16) | 0.71224 (17) | 0.05535 (14) | 0.0504 (6) | |
N2 | −0.09345 (16) | 0.62316 (16) | −0.04985 (13) | 0.0462 (5) | |
N3 | 0.02492 (16) | 0.67951 (17) | 0.05559 (13) | 0.0496 (5) | |
N4 | 0.43436 (15) | 0.80125 (15) | 0.68476 (13) | 0.0430 (5) | |
N5 | 0.26707 (15) | 0.84091 (15) | 0.68728 (13) | 0.0433 (5) | |
N6 | 0.2860 (2) | 0.9473 (2) | 0.30043 (16) | 0.0658 (7) | |
H6A | 0.2520 | 0.9213 | 0.2596 | 0.079* | |
H6B | 0.3028 | 1.0035 | 0.2963 | 0.079* | |
N7 | 0.0355 (2) | 0.55217 (19) | 0.42562 (16) | 0.0660 (7) | |
H7A | 0.0729 | 0.5776 | 0.4647 | 0.079* | |
H7B | 0.0207 | 0.4954 | 0.4294 | 0.079* | |
N14 | 0.39019 (17) | 0.89462 (15) | 0.78988 (13) | 0.0461 (5) | |
N40 | 0.23749 (17) | 0.14946 (17) | 0.08463 (16) | 0.0554 (6) | |
H40A | 0.2080 | 0.1294 | 0.1296 | 0.066* | |
H40B | 0.1937 | 0.1813 | 0.0514 | 0.066* | |
N41 | 0.43332 (16) | 0.12584 (15) | 0.08443 (14) | 0.0458 (5) | |
H41C | 0.4586 | 0.1405 | 0.0358 | 0.055* | |
H41D | 0.4830 | 0.1147 | 0.1233 | 0.055* | |
N42 | 0.46835 (16) | 0.30603 (15) | 0.16217 (14) | 0.0461 (5) | |
H42C | 0.5066 | 0.2749 | 0.2007 | 0.055* | |
H42D | 0.5037 | 0.3191 | 0.1185 | 0.055* | |
N43 | 0.27380 (16) | 0.33553 (16) | 0.15799 (13) | 0.0477 (5) | |
H43C | 0.2198 | 0.3429 | 0.1229 | 0.057* | |
H43D | 0.2557 | 0.3271 | 0.2105 | 0.057* | |
O1 | −0.22794 (15) | 0.79241 (15) | 0.16018 (12) | 0.0591 (5) | |
O2 | −0.06869 (16) | 0.85104 (14) | 0.13044 (13) | 0.0615 (5) | |
O3 | 0.34000 (14) | 0.66618 (13) | 0.61940 (12) | 0.0529 (5) | |
O4 | 0.50671 (14) | 0.69867 (14) | 0.58861 (12) | 0.0535 (5) | |
O9 | 0.1364 (2) | 0.6342 (2) | 0.5904 (3) | 0.1116 (11) | |
H4O | 0.175 (4) | 0.671 (4) | 0.568 (3) | 0.167* | |
H50 | 0.150 (5) | 0.642 (4) | 0.6442 (9) | 0.167* | |
O41 | 0.36198 (16) | 0.14826 (17) | 0.27351 (13) | 0.0614 (5) | |
H41E | 0.3165 (18) | 0.178 (3) | 0.302 (2) | 0.092* | |
H41F | 0.4245 (8) | 0.151 (3) | 0.285 (2) | 0.092* | |
O42 | 0.35160 (16) | 0.31031 (16) | −0.01528 (13) | 0.0589 (5) | |
H42E | 0.3853 (16) | 0.282 (2) | −0.0495 (18) | 0.088* | |
H42F | 0.2910 (7) | 0.304 (3) | −0.031 (2) | 0.088* | |
S1 | 0.41217 (5) | 0.73535 (4) | 0.60728 (4) | 0.04159 (15) | |
S2 | −0.12941 (5) | 0.77162 (5) | 0.13779 (4) | 0.04671 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0375 (13) | 0.0555 (15) | 0.0370 (12) | 0.0045 (11) | 0.0018 (10) | 0.0053 (11) |
C3 | 0.0516 (16) | 0.0493 (15) | 0.0480 (14) | 0.0007 (12) | 0.0058 (12) | −0.0010 (12) |
C4 | 0.0480 (16) | 0.0512 (16) | 0.0612 (17) | 0.0071 (12) | 0.0142 (13) | 0.0059 (13) |
C5 | 0.0350 (13) | 0.0644 (18) | 0.0537 (15) | 0.0048 (12) | 0.0049 (12) | 0.0113 (13) |
C7 | 0.0406 (13) | 0.0473 (14) | 0.0411 (12) | 0.0004 (11) | 0.0059 (11) | −0.0046 (10) |
C8 | 0.0463 (15) | 0.0514 (15) | 0.0462 (14) | −0.0058 (12) | 0.0050 (12) | −0.0041 (11) |
C9 | 0.0576 (17) | 0.0444 (14) | 0.0539 (15) | −0.0032 (12) | 0.0121 (13) | 0.0002 (12) |
C10 | 0.0494 (15) | 0.0537 (16) | 0.0420 (13) | 0.0088 (12) | 0.0133 (12) | 0.0031 (11) |
C11 | 0.0508 (15) | 0.0541 (15) | 0.0410 (13) | 0.0027 (13) | −0.0004 (12) | −0.0028 (11) |
C12 | 0.0506 (15) | 0.0426 (14) | 0.0444 (14) | −0.0002 (11) | −0.0006 (12) | −0.0034 (10) |
C13 | 0.0480 (15) | 0.0576 (16) | 0.0434 (14) | 0.0026 (13) | −0.0052 (12) | −0.0087 (12) |
C14 | 0.0471 (15) | 0.0474 (14) | 0.0456 (14) | −0.0009 (11) | 0.0006 (12) | −0.0060 (11) |
C15 | 0.0385 (13) | 0.0440 (13) | 0.0395 (12) | 0.0036 (10) | 0.0023 (10) | −0.0035 (10) |
C16 | 0.0485 (15) | 0.0468 (14) | 0.0436 (13) | −0.0010 (12) | 0.0002 (11) | −0.0057 (11) |
C17 | 0.0549 (16) | 0.0440 (14) | 0.0493 (15) | 0.0023 (12) | 0.0021 (13) | −0.0021 (11) |
C18 | 0.0432 (14) | 0.0584 (17) | 0.0447 (14) | 0.0108 (12) | 0.0032 (11) | 0.0004 (12) |
C21 | 0.0388 (13) | 0.0437 (13) | 0.0352 (12) | −0.0001 (10) | 0.0008 (10) | 0.0064 (10) |
C23 | 0.0610 (18) | 0.0622 (18) | 0.0409 (14) | 0.0006 (14) | 0.0062 (13) | −0.0079 (12) |
C24 | 0.0513 (17) | 0.0659 (19) | 0.0581 (17) | 0.0049 (14) | 0.0181 (14) | −0.0030 (14) |
C25 | 0.0394 (14) | 0.0604 (17) | 0.0524 (15) | 0.0028 (12) | 0.0067 (12) | 0.0071 (13) |
C41 | 0.0642 (19) | 0.0492 (16) | 0.0539 (16) | 0.0057 (14) | 0.0003 (14) | −0.0075 (13) |
C42 | 0.0551 (17) | 0.0502 (16) | 0.0618 (17) | −0.0040 (13) | −0.0039 (14) | −0.0110 (13) |
C43 | 0.078 (2) | 0.059 (2) | 0.101 (3) | −0.0109 (18) | −0.020 (2) | −0.0162 (19) |
C44 | 0.080 (2) | 0.0495 (18) | 0.086 (2) | −0.0042 (16) | 0.005 (2) | −0.0081 (16) |
Zn1 | 0.03700 (17) | 0.04571 (18) | 0.04456 (18) | −0.00063 (13) | 0.00060 (12) | −0.00037 (13) |
N1 | 0.0361 (11) | 0.0736 (16) | 0.0405 (11) | 0.0080 (11) | −0.0025 (9) | −0.0048 (11) |
N2 | 0.0439 (12) | 0.0549 (13) | 0.0396 (11) | 0.0014 (10) | 0.0012 (9) | 0.0019 (9) |
N3 | 0.0370 (12) | 0.0710 (16) | 0.0401 (11) | 0.0015 (10) | −0.0006 (9) | 0.0025 (10) |
N4 | 0.0332 (10) | 0.0544 (12) | 0.0408 (11) | 0.0028 (9) | −0.0012 (9) | −0.0033 (9) |
N5 | 0.0345 (11) | 0.0531 (12) | 0.0419 (11) | 0.0018 (9) | −0.0003 (9) | 0.0010 (9) |
N6 | 0.0741 (18) | 0.0692 (17) | 0.0518 (14) | 0.0071 (14) | −0.0103 (13) | 0.0089 (12) |
N7 | 0.086 (2) | 0.0615 (16) | 0.0506 (14) | 0.0084 (14) | 0.0059 (13) | 0.0157 (12) |
N14 | 0.0475 (13) | 0.0536 (13) | 0.0367 (10) | 0.0028 (10) | −0.0009 (9) | −0.0021 (9) |
N40 | 0.0436 (13) | 0.0655 (15) | 0.0561 (13) | −0.0103 (11) | −0.0021 (11) | 0.0073 (12) |
N41 | 0.0472 (13) | 0.0459 (12) | 0.0436 (11) | 0.0027 (10) | −0.0007 (10) | 0.0002 (9) |
N42 | 0.0387 (11) | 0.0485 (12) | 0.0504 (12) | −0.0005 (10) | 0.0004 (10) | 0.0025 (10) |
N43 | 0.0419 (12) | 0.0616 (14) | 0.0393 (11) | 0.0076 (10) | 0.0008 (9) | −0.0010 (10) |
O1 | 0.0468 (11) | 0.0807 (14) | 0.0499 (11) | 0.0163 (10) | 0.0052 (9) | −0.0066 (10) |
O2 | 0.0672 (14) | 0.0574 (12) | 0.0597 (12) | −0.0004 (10) | 0.0029 (10) | 0.0115 (10) |
O3 | 0.0524 (11) | 0.0454 (10) | 0.0608 (11) | −0.0035 (8) | 0.0029 (9) | 0.0025 (8) |
O4 | 0.0456 (11) | 0.0605 (12) | 0.0545 (11) | 0.0147 (9) | 0.0058 (9) | −0.0026 (9) |
O9 | 0.0672 (18) | 0.080 (2) | 0.189 (3) | −0.0044 (15) | 0.022 (2) | 0.003 (2) |
O41 | 0.0508 (12) | 0.0792 (15) | 0.0537 (11) | −0.0074 (11) | 0.0019 (10) | −0.0073 (10) |
O42 | 0.0486 (11) | 0.0738 (14) | 0.0539 (11) | −0.0004 (10) | 0.0008 (9) | −0.0062 (10) |
S1 | 0.0385 (3) | 0.0445 (3) | 0.0416 (3) | 0.0035 (3) | 0.0019 (3) | −0.0010 (3) |
S2 | 0.0422 (3) | 0.0576 (4) | 0.0401 (3) | 0.0059 (3) | 0.0016 (3) | 0.0005 (3) |
Zn—O41 | 2.68 (2) | C25—N5 | 1.326 (4) |
Zn—O42 | 2.49 (2) | C25—H25 | 0.9300 |
C1—N2 | 1.351 (3) | C41—N43 | 1.476 (4) |
C1—N3 | 1.355 (3) | C41—C42 | 1.494 (4) |
C1—N1 | 1.368 (3) | C41—H41A | 0.9700 |
C3—N2 | 1.330 (4) | C41—H41B | 0.9700 |
C3—C4 | 1.368 (4) | C42—N42 | 1.479 (4) |
C3—H3 | 0.9300 | C42—H42A | 0.9700 |
C4—C5 | 1.371 (4) | C42—H42B | 0.9700 |
C4—H4 | 0.9300 | C43—C44 | 1.465 (5) |
C5—N3 | 1.331 (4) | C43—N40 | 1.485 (5) |
C5—H5 | 0.9300 | C43—H43A | 0.9700 |
C7—C8 | 1.382 (4) | C43—H43B | 0.9700 |
C7—C12 | 1.386 (4) | C44—N41 | 1.463 (4) |
C7—S2 | 1.759 (3) | C44—H44A | 0.9700 |
C8—C9 | 1.374 (4) | C44—H44B | 0.9700 |
C8—H8 | 0.9300 | Zn1—N43 | 1.996 (2) |
C9—C10 | 1.406 (4) | Zn1—N41 | 2.009 (2) |
C9—H9 | 0.9300 | Zn1—N42 | 2.015 (2) |
C10—N7 | 1.363 (3) | Zn1—N40 | 2.016 (2) |
C10—C11 | 1.395 (4) | N1—S2 | 1.576 (2) |
C11—C12 | 1.379 (4) | N4—S1 | 1.579 (2) |
C11—H11 | 0.9300 | N6—H6A | 0.8600 |
C12—H12 | 0.9300 | N6—H6B | 0.8600 |
C13—C14 | 1.378 (4) | N7—H7A | 0.8600 |
C13—C18 | 1.391 (4) | N7—H7B | 0.8600 |
C13—H13 | 0.9300 | N40—H40A | 0.9000 |
C14—C15 | 1.387 (4) | N40—H40B | 0.9000 |
C14—H14 | 0.9300 | N41—H41C | 0.9000 |
C15—C16 | 1.384 (4) | N41—H41D | 0.9000 |
C15—S1 | 1.772 (3) | N42—H42C | 0.9000 |
C16—C17 | 1.378 (4) | N42—H42D | 0.9000 |
C16—H16 | 0.9300 | N43—H43C | 0.9000 |
C17—C18 | 1.403 (4) | N43—H43D | 0.9000 |
C17—H17 | 0.9300 | O1—S2 | 1.459 (2) |
C18—N6 | 1.374 (3) | O2—S2 | 1.442 (2) |
C21—N14 | 1.353 (3) | O3—S1 | 1.442 (2) |
C21—N5 | 1.354 (3) | O4—S1 | 1.4581 (19) |
C21—N4 | 1.366 (3) | O9—H4O | 0.85 (6) |
C23—N14 | 1.322 (4) | O9—H50 | 0.87 (2) |
C23—C24 | 1.367 (4) | O41—H41E | 0.910 (16) |
C23—H23 | 0.9300 | O41—H41F | 0.865 (10) |
C24—C25 | 1.377 (4) | O42—H42E | 0.85 (3) |
C24—H24 | 0.9300 | O42—H42F | 0.855 (10) |
N2—C1—N3 | 124.3 (2) | H42A—C42—H42B | 108.5 |
N2—C1—N1 | 113.9 (2) | C44—C43—N40 | 110.5 (3) |
N3—C1—N1 | 121.8 (2) | C44—C43—H43A | 109.5 |
N2—C3—C4 | 123.5 (3) | N40—C43—H43A | 109.5 |
N2—C3—H3 | 118.3 | C44—C43—H43B | 109.5 |
C4—C3—H3 | 118.3 | N40—C43—H43B | 109.5 |
C3—C4—C5 | 116.1 (3) | H43A—C43—H43B | 108.1 |
C3—C4—H4 | 121.9 | N41—C44—C43 | 109.6 (3) |
C5—C4—H4 | 121.9 | N41—C44—H44A | 109.8 |
N3—C5—C4 | 123.3 (3) | C43—C44—H44A | 109.8 |
N3—C5—H5 | 118.3 | N41—C44—H44B | 109.8 |
C4—C5—H5 | 118.3 | C43—C44—H44B | 109.8 |
C8—C7—C12 | 119.7 (2) | H44A—C44—H44B | 108.2 |
C8—C7—S2 | 120.6 (2) | N43—Zn1—N41 | 178.06 (9) |
C12—C7—S2 | 119.5 (2) | N43—Zn1—N42 | 84.76 (9) |
C9—C8—C7 | 120.7 (2) | N41—Zn1—N42 | 93.93 (9) |
C9—C8—H8 | 119.7 | N43—Zn1—N40 | 96.55 (10) |
C7—C8—H8 | 119.7 | N41—Zn1—N40 | 84.79 (10) |
C8—C9—C10 | 120.3 (3) | N42—Zn1—N40 | 178.08 (10) |
C8—C9—H9 | 119.8 | C1—N1—S2 | 121.48 (18) |
C10—C9—H9 | 119.8 | C3—N2—C1 | 116.4 (2) |
N7—C10—C11 | 120.8 (3) | C5—N3—C1 | 116.3 (2) |
N7—C10—C9 | 120.9 (3) | C21—N4—S1 | 120.97 (17) |
C11—C10—C9 | 118.3 (2) | C25—N5—C21 | 116.6 (2) |
C12—C11—C10 | 120.9 (3) | C18—N6—H6A | 120.0 |
C12—C11—H11 | 119.5 | C18—N6—H6B | 120.0 |
C10—C11—H11 | 119.5 | H6A—N6—H6B | 120.0 |
C11—C12—C7 | 120.0 (3) | C10—N7—H7A | 120.0 |
C11—C12—H12 | 120.0 | C10—N7—H7B | 120.0 |
C7—C12—H12 | 120.0 | H7A—N7—H7B | 120.0 |
C14—C13—C18 | 121.1 (2) | C23—N14—C21 | 116.2 (2) |
C14—C13—H13 | 119.5 | C43—N40—Zn1 | 108.2 (2) |
C18—C13—H13 | 119.5 | C43—N40—H40A | 110.0 |
C13—C14—C15 | 120.2 (3) | Zn1—N40—H40A | 110.0 |
C13—C14—H14 | 119.9 | C43—N40—H40B | 110.0 |
C15—C14—H14 | 119.9 | Zn1—N40—H40B | 110.0 |
C16—C15—C14 | 119.3 (2) | H40A—N40—H40B | 108.4 |
C16—C15—S1 | 120.92 (19) | C44—N41—Zn1 | 109.12 (19) |
C14—C15—S1 | 119.7 (2) | C44—N41—H41C | 109.9 |
C17—C16—C15 | 120.6 (2) | Zn1—N41—H41C | 109.9 |
C17—C16—H16 | 119.7 | C44—N41—H41D | 109.9 |
C15—C16—H16 | 119.7 | Zn1—N41—H41D | 109.9 |
C16—C17—C18 | 120.5 (3) | H41C—N41—H41D | 108.3 |
C16—C17—H17 | 119.8 | C42—N42—Zn1 | 109.26 (17) |
C18—C17—H17 | 119.8 | C42—N42—H42C | 109.8 |
N6—C18—C13 | 121.0 (3) | Zn1—N42—H42C | 109.8 |
N6—C18—C17 | 120.8 (3) | C42—N42—H42D | 109.8 |
C13—C18—C17 | 118.2 (2) | Zn1—N42—H42D | 109.8 |
N14—C21—N5 | 124.2 (2) | H42C—N42—H42D | 108.3 |
N14—C21—N4 | 114.2 (2) | C41—N43—Zn1 | 105.90 (17) |
N5—C21—N4 | 121.7 (2) | C41—N43—H43C | 110.6 |
N14—C23—C24 | 124.1 (3) | Zn1—N43—H43C | 110.6 |
N14—C23—H23 | 117.9 | C41—N43—H43D | 110.6 |
C24—C23—H23 | 117.9 | Zn1—N43—H43D | 110.6 |
C23—C24—C25 | 115.6 (3) | H43C—N43—H43D | 108.7 |
C23—C24—H24 | 122.2 | H4O—O9—H50 | 104 (5) |
C25—C24—H24 | 122.2 | H41E—O41—H41F | 126 (2) |
N5—C25—C24 | 123.3 (3) | H42E—O42—H42F | 109 (3) |
N5—C25—H25 | 118.4 | O3—S1—O4 | 113.65 (13) |
C24—C25—H25 | 118.4 | O3—S1—N4 | 114.71 (12) |
N43—C41—C42 | 107.6 (2) | O4—S1—N4 | 105.36 (11) |
N43—C41—H41A | 110.2 | O3—S1—C15 | 107.48 (12) |
C42—C41—H41A | 110.2 | O4—S1—C15 | 106.41 (12) |
N43—C41—H41B | 110.2 | N4—S1—C15 | 108.86 (12) |
C42—C41—H41B | 110.2 | O2—S2—O1 | 113.89 (14) |
H41A—C41—H41B | 108.5 | O2—S2—N1 | 114.70 (13) |
N42—C42—C41 | 107.7 (2) | O1—S2—N1 | 104.72 (12) |
N42—C42—H42A | 110.2 | O2—S2—C7 | 107.46 (12) |
C41—C42—H42A | 110.2 | O1—S2—C7 | 106.39 (12) |
N42—C42—H42B | 110.2 | N1—S2—C7 | 109.35 (13) |
C41—C42—H42B | 110.2 | ||
C15—S1—N4—C21 | 67.9 (2) | S2—N1—C1—N3 | 0.0 (4) |
C7—S2—N1—C1 | −58.9 (3) | C16—C15—S1—N4 | 25.8 (3) |
S1—N4—C21—N5 | −4.8 (3) | C8—C7—S2—N1 | −34.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6B···O41i | 0.86 | 2.31 | 3.165 (4) | 173 |
N7—H7A···O9 | 0.86 | 2.28 | 3.114 (5) | 164 |
N7—H7B···O2ii | 0.86 | 2.43 | 3.124 (4) | 138 |
N7—H7B···N7iii | 0.86 | 2.59 | 3.046 (5) | 114 |
N40—H40B···N1iv | 0.90 | 2.37 | 3.204 (3) | 155 |
N41—H41C···O4v | 0.90 | 2.24 | 3.128 (3) | 167 |
N41—H41D···N14vi | 0.90 | 2.14 | 3.036 (3) | 172 |
N42—H42C···N4vi | 0.90 | 2.24 | 3.115 (3) | 165 |
N43—H43C···N2iv | 0.90 | 2.07 | 2.968 (3) | 172 |
N43—H43D···O1ii | 0.90 | 2.19 | 3.080 (3) | 172 |
O9—H4O···O3 | 0.85 (6) | 2.35 (6) | 2.839 (4) | 116 (5) |
O41—H41E···O1ii | 0.91 (2) | 2.18 (2) | 3.046 (3) | 158 (4) |
O41—H41F···N4vi | 0.87 (1) | 2.08 (2) | 2.920 (3) | 163 (3) |
O42—H42E···O4v | 0.85 (3) | 2.06 (2) | 2.862 (3) | 158 (3) |
O42—H42F···N1iv | 0.86 (1) | 2.03 (1) | 2.884 (3) | 174 (3) |
O42—H42F···O1iv | 0.86 (1) | 2.59 (3) | 3.142 (3) | 123 (2) |
Symmetry codes: (i) x, y+1, z; (ii) −x, y−1/2, −z+1/2; (iii) −x, −y+1, −z+1; (iv) −x, −y+1, −z; (v) −x+1, y−1/2, −z+1/2; (vi) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C4H8N4)(H2O)2](C10H9N4O2S)2·H2O |
Mr | 738.17 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.7400 (5), 14.6581 (7), 15.9408 (6) |
β (°) | 94.510 (3) |
V (Å3) | 3200.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.96 |
Crystal size (mm) | 0.38 × 0.33 × 0.22 |
Data collection | |
Diffractometer | Stoe IPDS 2 diffractometer |
Absorption correction | Integration X-RED32 (Stoe & Cie, 2002) |
Tmin, Tmax | 0.749, 0.829 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 32597, 6655, 4864 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.630 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.115, 0.96 |
No. of reflections | 6655 |
No. of parameters | 433 |
No. of restraints | 9 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.41, −0.57 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6B···O41i | 0.86 | 2.31 | 3.165 (4) | 173 |
N7—H7A···O9 | 0.86 | 2.28 | 3.114 (5) | 164 |
N7—H7B···O2ii | 0.86 | 2.43 | 3.124 (4) | 138 |
N7—H7B···N7iii | 0.86 | 2.59 | 3.046 (5) | 114 |
N40—H40B···N1iv | 0.90 | 2.37 | 3.204 (3) | 155 |
N41—H41C···O4v | 0.90 | 2.24 | 3.128 (3) | 167 |
N41—H41D···N14vi | 0.90 | 2.14 | 3.036 (3) | 172 |
N42—H42C···N4vi | 0.90 | 2.24 | 3.115 (3) | 165 |
N43—H43C···N2iv | 0.90 | 2.07 | 2.968 (3) | 172 |
N43—H43D···O1ii | 0.90 | 2.19 | 3.080 (3) | 172 |
O9—H4O···O3 | 0.85 (6) | 2.35 (6) | 2.839 (4) | 116 (5) |
O41—H41E···O1ii | 0.910 (16) | 2.18 (2) | 3.046 (3) | 158 (4) |
O41—H41F···N4vi | 0.865 (10) | 2.082 (16) | 2.920 (3) | 163 (3) |
O42—H42E···O4v | 0.85 (3) | 2.056 (15) | 2.862 (3) | 158 (3) |
O42—H42F···N1iv | 0.855 (10) | 2.032 (10) | 2.884 (3) | 174 (3) |
O42—H42F···O1iv | 0.855 (10) | 2.59 (3) | 3.142 (3) | 123 (2) |
Symmetry codes: (i) x, y+1, z; (ii) −x, y−1/2, −z+1/2; (iii) −x, −y+1, −z+1; (iv) −x, −y+1, −z; (v) −x+1, y−1/2, −z+1/2; (vi) −x+1, −y+1, −z+1. |
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Many sulfanilamide derivatives, such as 2-sulfanilamidopyrimidine (sulfadiazine), possess antibacterial activity. Thus, sulfadiazine compounds are widely used for their bacterial action (Nogrady, 1988; Silverman, 1992) and zinc salts of sulfadiazine are used to prevent bacterial infection in both humans and animals during the treatment of burns (Baezinger & Strauss, 1976; Cook & Turner, 1975). The pharmacological activity of these types of molecules is often enhanced by complexation with metal ions (Bult & Sigel, 1983; Casanova et al., 1993). These metal complexes are largely insoluble, working through the slow release of the metal ions from these materials. Because the slow release of the metal ions from these drugs is strongly dependent on their binding nature, it is important to understand the coordination environment around the metal. Although interesting structural results have been described in the literature (Baezinger et al., 1983; Built et al., 1981; Brown et al., 1987; Garcia Raso et al., 1997), mixed-ligand complexes of 2-sulfanilamidopyrimidine have not been prepared and investigated sufficiently to date. Therefore, in the present paper, we report on the synthesis and spectroscopic characterization of the title CuII ZnII?–2-sulfanilamidopyrimidine (H—SD)–ethylenediamine (en) mixed-ligand complex, (I).
The title complex contains octahedral elongated (ethylendiamine)zinc(II) cations counterbalanced with sulfadiazine anions. The two ethylendiamine moieties are trans to each other (Fig. 1). The ethylendiamine ligand and ZnII cation form a five-membered ring, as has already been observed in an analogous Pt complex (Reference?). The Zn—N bond distances are consistent with those in a related structure (Fu et al., 2005). The five-membered rings of the groups are in an envelope conformation with atoms C41 and C44 forming the flap, as shown in Fig. 1. Sulfadiazine molecules can exist in different conformations as a result of rotation across the C—S, S—N and N—C bonds (Kokila et al., 1995). The three dihedral angles describing these conformations of the sulfadiazine ligands in (I) are C15—S1—N4—C21/C7—S2—N1—C1 = 67.9 (2)/-58.9 (2)°, S1—N4—C21—N5/S2—N1—C1—N3 = −4.8 (3)/0.0 (4)° and C16—C15—S1—N4/C8—C7—S2—N1 = 25.8 (3)/-34.8 (3). Thus, both molecules have roughly the same gauche conformation when viewed along the S—N axis.
The H atoms of the coordinated water molecules are engaged in hydrogen bonding with the sulfadiazine anions, resulting in the formation of extended chains. Moreover, there are also N—H···O hydrogen bonds, resulting in an intricate three-dimensional network (Table 1, Fig. 2)