Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802021864/na6189sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802021864/na6189Isup2.hkl |
CCDC reference: 202978
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.024
- wR factor = 0.060
- Data-to-parameter ratio = 14.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.29 From the CIF: _reflns_number_total 3811 Count of symmetry unique reflns 2815 Completeness (_total/calc) 135.38% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 996 Fraction of Friedel pairs measured 0.354 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
[Zn(C2H3O2)2(C7H6N2S)2] | Dx = 1.509 Mg m−3 |
Mr = 483.89 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 7544 reflections |
a = 8.5471 (7) Å | θ = 2.4–28.3° |
b = 27.547 (2) Å | µ = 1.38 mm−1 |
c = 9.0485 (8) Å | T = 293 K |
V = 2130.4 (3) Å3 | Block, colorless |
Z = 4 | 0.40 × 0.36 × 0.32 mm |
F(000) = 992 |
Siemens SMART CCD area-detector diffractometer | 3811 independent reflections |
Radiation source: fine-focus sealed tube | 3423 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.4° |
ω scans | h = −11→11 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −36→33 |
Tmin = 0.608, Tmax = 0.666 | l = −7→12 |
12903 measured reflections |
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)] = 0.024 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.060 | w = 1/[σ2(Fo2) + (0.033P)2 + 0.1054P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
3811 reflections | Δρmax = 0.19 e Å−3 |
264 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Absolute structure: (Flack, 1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.017 (9) |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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 | ||
Zn1 | 0.86524 (3) | 0.620875 (7) | 0.66460 (4) | 0.03651 (7) | |
S1 | 0.73336 (10) | 0.76943 (3) | 0.48023 (10) | 0.0686 (2) | |
S2 | 0.78644 (10) | 0.47845 (2) | 0.41383 (9) | 0.0619 (2) | |
O1 | 0.72280 (18) | 0.62668 (5) | 0.8334 (2) | 0.0406 (4) | |
O2 | 0.8581 (2) | 0.56659 (7) | 0.9255 (3) | 0.0707 (7) | |
O3 | 1.09278 (18) | 0.61168 (5) | 0.6828 (3) | 0.0455 (4) | |
O4 | 1.0691 (2) | 0.68250 (6) | 0.7921 (2) | 0.0496 (4) | |
N1 | 0.8126 (2) | 0.68116 (7) | 0.5448 (2) | 0.0394 (4) | |
N2 | 0.6896 (3) | 0.72383 (8) | 0.7361 (3) | 0.0563 (6) | |
H2A | 0.6950 | 0.6996 | 0.7958 | 0.068* | |
H2B | 0.6476 | 0.7506 | 0.7646 | 0.068* | |
N3 | 0.7956 (2) | 0.56299 (6) | 0.5405 (2) | 0.0407 (5) | |
N4 | 1.0252 (3) | 0.51751 (8) | 0.5601 (4) | 0.0662 (7) | |
H4A | 1.0717 | 0.5398 | 0.6100 | 0.079* | |
H4B | 1.0735 | 0.4910 | 0.5395 | 0.079* | |
C1 | 0.7461 (3) | 0.71995 (8) | 0.6004 (3) | 0.0409 (5) | |
C2 | 0.8263 (4) | 0.73522 (12) | 0.3456 (3) | 0.0609 (7) | |
C3 | 0.8666 (5) | 0.74944 (19) | 0.2023 (5) | 0.0977 (14) | |
H3A | 0.8426 | 0.7802 | 0.1667 | 0.117* | |
C4 | 0.9436 (6) | 0.71578 (19) | 0.1160 (5) | 0.1009 (14) | |
H4C | 0.9713 | 0.7239 | 0.0197 | 0.121* | |
C5 | 0.9801 (4) | 0.67038 (15) | 0.1692 (5) | 0.0834 (10) | |
H5A | 1.0330 | 0.6487 | 0.1083 | 0.100* | |
C6 | 0.9406 (4) | 0.65612 (12) | 0.3108 (3) | 0.0624 (8) | |
H6A | 0.9667 | 0.6254 | 0.3455 | 0.075* | |
C7 | 0.8606 (3) | 0.68893 (10) | 0.3997 (3) | 0.0454 (6) | |
C8 | 0.8807 (3) | 0.52397 (8) | 0.5154 (3) | 0.0457 (6) | |
C9 | 0.6199 (3) | 0.51519 (10) | 0.4028 (3) | 0.0528 (7) | |
C10 | 0.4801 (4) | 0.50537 (13) | 0.3327 (4) | 0.0687 (9) | |
H10A | 0.4645 | 0.4762 | 0.2832 | 0.082* | |
C11 | 0.3642 (4) | 0.54019 (17) | 0.3381 (4) | 0.0790 (11) | |
H11A | 0.2680 | 0.5342 | 0.2936 | 0.095* | |
C12 | 0.3901 (3) | 0.58407 (15) | 0.4096 (5) | 0.0740 (10) | |
H12A | 0.3113 | 0.6074 | 0.4108 | 0.089* | |
C13 | 0.5304 (3) | 0.59377 (11) | 0.4789 (4) | 0.0577 (7) | |
H13A | 0.5464 | 0.6233 | 0.5262 | 0.069* | |
C14 | 0.6470 (3) | 0.55886 (9) | 0.4769 (3) | 0.0441 (6) | |
C15 | 0.7522 (3) | 0.59636 (8) | 0.9361 (3) | 0.0429 (6) | |
C16 | 0.6487 (4) | 0.59846 (15) | 1.0702 (4) | 0.0742 (10) | |
H16A | 0.7044 | 0.5860 | 1.1542 | 0.111* | |
H16B | 0.5567 | 0.5792 | 1.0535 | 0.111* | |
H16C | 0.6190 | 0.6315 | 1.0887 | 0.111* | |
C17 | 1.1488 (3) | 0.64735 (8) | 0.7562 (3) | 0.0384 (5) | |
C18 | 1.3175 (3) | 0.64447 (12) | 0.8023 (4) | 0.0651 (8) | |
H18A | 1.3720 | 0.6728 | 0.7681 | 0.098* | |
H18B | 1.3643 | 0.6160 | 0.7601 | 0.098* | |
H18C | 1.3238 | 0.6428 | 0.9081 | 0.098* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.04038 (12) | 0.02557 (10) | 0.04358 (13) | 0.00296 (9) | 0.00364 (15) | −0.00700 (12) |
S1 | 0.0949 (5) | 0.0515 (4) | 0.0592 (4) | 0.0246 (4) | 0.0129 (4) | 0.0249 (3) |
S2 | 0.0833 (5) | 0.0362 (3) | 0.0661 (5) | −0.0105 (3) | 0.0047 (4) | −0.0229 (3) |
O1 | 0.0469 (9) | 0.0332 (8) | 0.0416 (9) | 0.0070 (7) | 0.0062 (8) | 0.0053 (7) |
O2 | 0.0645 (12) | 0.0489 (11) | 0.0986 (19) | 0.0175 (9) | 0.0057 (12) | 0.0290 (12) |
O3 | 0.0422 (7) | 0.0307 (7) | 0.0636 (13) | −0.0009 (6) | −0.0040 (11) | −0.0086 (9) |
O4 | 0.0550 (10) | 0.0374 (9) | 0.0566 (11) | −0.0052 (8) | 0.0099 (9) | −0.0109 (8) |
N1 | 0.0466 (10) | 0.0339 (9) | 0.0378 (11) | 0.0013 (8) | 0.0019 (9) | −0.0021 (8) |
N2 | 0.0886 (17) | 0.0306 (10) | 0.0497 (13) | 0.0218 (11) | 0.0211 (14) | 0.0071 (9) |
N3 | 0.0447 (11) | 0.0320 (9) | 0.0455 (12) | −0.0027 (8) | 0.0058 (9) | −0.0121 (8) |
N4 | 0.0630 (15) | 0.0399 (12) | 0.096 (2) | 0.0136 (10) | −0.0065 (14) | −0.0284 (13) |
C1 | 0.0475 (13) | 0.0329 (11) | 0.0422 (13) | 0.0078 (10) | 0.0039 (11) | 0.0036 (9) |
C2 | 0.0729 (17) | 0.0668 (19) | 0.0429 (16) | 0.0048 (15) | 0.0026 (14) | 0.0132 (13) |
C3 | 0.125 (3) | 0.112 (3) | 0.056 (3) | 0.007 (3) | 0.017 (2) | 0.028 (2) |
C4 | 0.124 (3) | 0.131 (4) | 0.047 (2) | −0.025 (3) | 0.025 (2) | 0.002 (2) |
C5 | 0.091 (2) | 0.106 (3) | 0.0536 (17) | −0.023 (2) | 0.023 (2) | −0.026 (2) |
C6 | 0.0678 (18) | 0.0644 (18) | 0.0550 (18) | −0.0151 (15) | 0.0127 (15) | −0.0214 (14) |
C7 | 0.0467 (13) | 0.0551 (15) | 0.0345 (13) | −0.0069 (11) | −0.0002 (11) | −0.0042 (11) |
C8 | 0.0590 (15) | 0.0305 (11) | 0.0476 (14) | −0.0018 (10) | 0.0079 (12) | −0.0135 (10) |
C9 | 0.0643 (16) | 0.0498 (14) | 0.0443 (14) | −0.0196 (12) | 0.0102 (13) | −0.0098 (12) |
C10 | 0.076 (2) | 0.076 (2) | 0.0539 (18) | −0.0328 (17) | −0.0007 (16) | −0.0145 (16) |
C11 | 0.0587 (18) | 0.115 (3) | 0.063 (2) | −0.030 (2) | −0.0039 (16) | −0.008 (2) |
C12 | 0.0473 (15) | 0.098 (3) | 0.076 (2) | −0.0015 (16) | −0.0017 (16) | −0.008 (2) |
C13 | 0.0465 (13) | 0.0625 (17) | 0.0641 (18) | −0.0043 (12) | 0.0045 (14) | −0.0134 (14) |
C14 | 0.0476 (13) | 0.0446 (13) | 0.0400 (13) | −0.0101 (10) | 0.0087 (11) | −0.0061 (10) |
C15 | 0.0446 (12) | 0.0368 (11) | 0.0472 (15) | −0.0074 (10) | −0.0015 (11) | 0.0090 (10) |
C16 | 0.074 (2) | 0.096 (3) | 0.0516 (19) | −0.0057 (18) | 0.0084 (16) | 0.0208 (19) |
C17 | 0.0407 (11) | 0.0365 (12) | 0.0381 (12) | −0.0111 (10) | 0.0072 (10) | 0.0054 (9) |
C18 | 0.0482 (14) | 0.0632 (19) | 0.084 (2) | −0.0071 (13) | −0.0082 (16) | 0.0008 (17) |
Zn1—O1 | 1.960 (2) | C3—H3A | 0.9300 |
Zn1—O3 | 1.968 (2) | C4—C5 | 1.376 (6) |
Zn1—N1 | 2.034 (2) | C4—H4C | 0.9300 |
Zn1—N3 | 2.039 (2) | C5—C6 | 1.381 (6) |
S1—C2 | 1.733 (3) | C5—H5A | 0.9300 |
S1—C1 | 1.747 (2) | C6—C7 | 1.390 (4) |
S2—C9 | 1.749 (3) | C6—H6A | 0.9300 |
S2—C8 | 1.751 (2) | C9—C10 | 1.380 (4) |
O1—C15 | 1.274 (3) | C9—C14 | 1.396 (4) |
O2—C15 | 1.225 (3) | C10—C11 | 1.380 (5) |
O3—C17 | 1.279 (3) | C10—H10A | 0.9300 |
O4—C17 | 1.228 (3) | C11—C12 | 1.389 (5) |
N1—C1 | 1.311 (3) | C11—H11A | 0.9300 |
N1—C7 | 1.391 (3) | C12—C13 | 1.379 (4) |
N2—C1 | 1.324 (3) | C12—H12A | 0.9300 |
N2—H2A | 0.8600 | C13—C14 | 1.385 (4) |
N2—H2B | 0.8600 | C13—H13A | 0.9300 |
N3—C8 | 1.317 (3) | C15—C16 | 1.503 (4) |
N3—C14 | 1.399 (3) | C16—H16A | 0.9600 |
N4—C8 | 1.312 (3) | C16—H16B | 0.9600 |
N4—H4A | 0.8600 | C16—H16C | 0.9600 |
N4—H4B | 0.8600 | C17—C18 | 1.502 (4) |
C2—C7 | 1.397 (4) | C18—H18A | 0.9600 |
C2—C3 | 1.398 (5) | C18—H18B | 0.9600 |
C3—C4 | 1.379 (6) | C18—H18C | 0.9600 |
O1—Zn1—O3 | 124.00 (9) | C6—C7—C2 | 119.6 (3) |
O1—Zn1—N1 | 102.21 (7) | N1—C7—C2 | 114.1 (2) |
O3—Zn1—N1 | 111.62 (8) | N4—C8—N3 | 125.3 (2) |
O1—Zn1—N3 | 108.15 (8) | N4—C8—S2 | 119.84 (18) |
O3—Zn1—N3 | 103.53 (8) | N3—C8—S2 | 114.87 (19) |
N1—Zn1—N3 | 106.27 (9) | C10—C9—C14 | 122.2 (3) |
C2—S1—C1 | 89.12 (13) | C10—C9—S2 | 128.1 (2) |
C9—S2—C8 | 89.41 (12) | C14—C9—S2 | 109.7 (2) |
C15—O1—Zn1 | 113.09 (14) | C9—C10—C11 | 118.0 (3) |
C17—O3—Zn1 | 108.34 (14) | C9—C10—H10A | 121.0 |
C1—N1—C7 | 111.4 (2) | C11—C10—H10A | 121.0 |
C1—N1—Zn1 | 123.83 (17) | C10—C11—C12 | 120.5 (3) |
C7—N1—Zn1 | 124.27 (16) | C10—C11—H11A | 119.8 |
C1—N2—H2A | 120.0 | C12—C11—H11A | 119.8 |
C1—N2—H2B | 120.0 | C13—C12—C11 | 121.3 (3) |
H2A—N2—H2B | 120.0 | C13—C12—H12A | 119.4 |
C8—N3—C14 | 111.4 (2) | C11—C12—H12A | 119.4 |
C8—N3—Zn1 | 124.85 (17) | C12—C13—C14 | 119.0 (3) |
C14—N3—Zn1 | 123.72 (15) | C12—C13—H13A | 120.5 |
C8—N4—H4A | 120.0 | C14—C13—H13A | 120.5 |
C8—N4—H4B | 120.0 | C13—C14—C9 | 119.0 (2) |
H4A—N4—H4B | 120.0 | C13—C14—N3 | 126.3 (2) |
N1—C1—N2 | 125.5 (2) | C9—C14—N3 | 114.7 (2) |
N1—C1—S1 | 115.08 (19) | O2—C15—O1 | 121.8 (2) |
N2—C1—S1 | 119.44 (18) | O2—C15—C16 | 121.6 (3) |
C7—C2—C3 | 121.9 (3) | O1—C15—C16 | 116.6 (2) |
C7—C2—S1 | 110.3 (2) | C15—C16—H16A | 109.5 |
C3—C2—S1 | 127.8 (3) | C15—C16—H16B | 109.5 |
C4—C3—C2 | 117.0 (4) | H16A—C16—H16B | 109.5 |
C4—C3—H3A | 121.5 | C15—C16—H16C | 109.5 |
C2—C3—H3A | 121.5 | H16A—C16—H16C | 109.5 |
C5—C4—C3 | 121.4 (4) | H16B—C16—H16C | 109.5 |
C5—C4—H4C | 119.3 | O4—C17—O3 | 122.3 (2) |
C3—C4—H4C | 119.3 | O4—C17—C18 | 120.1 (2) |
C4—C5—C6 | 121.8 (4) | O3—C17—C18 | 117.6 (2) |
C4—C5—H5A | 119.1 | C17—C18—H18A | 109.5 |
C6—C5—H5A | 119.1 | C17—C18—H18B | 109.5 |
C5—C6—C7 | 118.2 (3) | H18A—C18—H18B | 109.5 |
C5—C6—H6A | 120.9 | C17—C18—H18C | 109.5 |
C7—C6—H6A | 120.9 | H18A—C18—H18C | 109.5 |
C6—C7—N1 | 126.2 (3) | H18B—C18—H18C | 109.5 |
O3—Zn1—O1—C15 | −42.79 (18) | Zn1—N1—C7—C6 | 5.1 (3) |
N1—Zn1—O1—C15 | −169.71 (16) | C1—N1—C7—C2 | −0.8 (3) |
N3—Zn1—O1—C15 | 78.41 (17) | Zn1—N1—C7—C2 | −172.88 (19) |
O1—Zn1—O3—C17 | −58.55 (19) | C3—C2—C7—C6 | 1.6 (5) |
N1—Zn1—O3—C17 | 64.2 (2) | S1—C2—C7—C6 | −177.7 (2) |
N3—Zn1—O3—C17 | 178.16 (17) | C3—C2—C7—N1 | 179.8 (3) |
O1—Zn1—N1—C1 | 22.0 (2) | S1—C2—C7—N1 | 0.4 (3) |
O3—Zn1—N1—C1 | −112.5 (2) | C14—N3—C8—N4 | 179.3 (3) |
N3—Zn1—N1—C1 | 135.3 (2) | Zn1—N3—C8—N4 | −3.6 (4) |
O1—Zn1—N1—C7 | −166.90 (18) | C14—N3—C8—S2 | −0.7 (3) |
O3—Zn1—N1—C7 | 58.6 (2) | Zn1—N3—C8—S2 | 176.41 (12) |
N3—Zn1—N1—C7 | −53.6 (2) | C9—S2—C8—N4 | −179.4 (3) |
O1—Zn1—N3—C8 | −118.0 (2) | C9—S2—C8—N3 | 0.6 (2) |
O3—Zn1—N3—C8 | 15.2 (2) | C8—S2—C9—C10 | 179.0 (3) |
N1—Zn1—N3—C8 | 132.9 (2) | C8—S2—C9—C14 | −0.3 (2) |
O1—Zn1—N3—C14 | 58.8 (2) | C14—C9—C10—C11 | −0.5 (5) |
O3—Zn1—N3—C14 | −168.1 (2) | S2—C9—C10—C11 | −179.8 (3) |
N1—Zn1—N3—C14 | −50.3 (2) | C9—C10—C11—C12 | 1.4 (6) |
C7—N1—C1—N2 | −179.5 (3) | C10—C11—C12—C13 | −1.1 (6) |
Zn1—N1—C1—N2 | −7.4 (4) | C11—C12—C13—C14 | −0.2 (6) |
C7—N1—C1—S1 | 0.9 (3) | C12—C13—C14—C9 | 1.0 (5) |
Zn1—N1—C1—S1 | 172.98 (11) | C12—C13—C14—N3 | 179.5 (3) |
C2—S1—C1—N1 | −0.6 (2) | C10—C9—C14—C13 | −0.7 (5) |
C2—S1—C1—N2 | 179.8 (3) | S2—C9—C14—C13 | 178.7 (2) |
C1—S1—C2—C7 | 0.1 (2) | C10—C9—C14—N3 | −179.4 (3) |
C1—S1—C2—C3 | −179.2 (4) | S2—C9—C14—N3 | 0.0 (3) |
C7—C2—C3—C4 | −0.6 (6) | C8—N3—C14—C13 | −178.1 (3) |
S1—C2—C3—C4 | 178.7 (3) | Zn1—N3—C14—C13 | 4.7 (4) |
C2—C3—C4—C5 | −0.5 (7) | C8—N3—C14—C9 | 0.4 (3) |
C3—C4—C5—C6 | 0.6 (7) | Zn1—N3—C14—C9 | −176.69 (19) |
C4—C5—C6—C7 | 0.5 (5) | Zn1—O1—C15—O2 | −1.1 (3) |
C5—C6—C7—N1 | −179.4 (3) | Zn1—O1—C15—C16 | 179.7 (2) |
C5—C6—C7—C2 | −1.6 (4) | Zn1—O3—C17—O4 | −6.7 (3) |
C1—N1—C7—C6 | 177.2 (3) | Zn1—O3—C17—C18 | 171.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 2.05 | 2.832 (3) | 151 |
N2—H2B···O4i | 0.86 | 1.98 | 2.824 (3) | 168 |
N4—H4A···O3 | 0.86 | 2.10 | 2.880 (3) | 152 |
N4—H4B···O2ii | 0.86 | 1.98 | 2.801 (3) | 159 |
Symmetry codes: (i) x−1/2, −y+3/2, z; (ii) −x+2, −y+1, z−1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register