Supporting information
CCDC references: 134761; 134762; 134763; 134764; 134765; 134766
Data collection: CAD4 (Enraf-Nonius, 1992) for (5), (6a), (6b), (6c), (7); KappaCCD (Enraf-Nonius, 1997) for (6d). Cell refinement: SET4 & CELDIM (Enraf-Nonius, 1992) for (5), (6a), (6b), (6c), (7); DENZO (Enraf-Nonius, 1997) for (6d). Data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989) for (5), (6a), (6b), (6c), (7); DENZO (Enraf-Nonius, 1997) for (6d). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a) for (5), (6b), (6c), (6d); SHELXS97 (Sheldrick, 1997) for (6a), (7). Program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997b) for (5), (6b), (6c); NRCVAX96 and SHELXL97 (Sheldrick, 1997) for (6a), (7); NRCVAX96 (Gabe et al., 1989) and SHELXL97 (Sheldrick, 1997b) for (6d). For all compounds, molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998). Software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PRPCIF97 (Ferguson, 1997) for (5), (6a), (7); NRCVAX96, SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998) for (6b), (6c), (6d).
2(C12H10O4S)·C4H4N2 | F(000) = 604 |
Mr = 580.64 | ? #Insert any comments here. |
Monoclinic, P21/a | Dx = 1.424 Mg m−3 |
Hall symbol: -P 2yab | Mo Kα radiation, λ = 0.7107 Å |
a = 8.3506 (9) Å | Cell parameters from 25 reflections |
b = 18.0102 (17) Å | θ = 9.5–20.4° |
c = 9.6360 (14) Å | µ = 0.25 mm−1 |
β = 110.869 (8)° | T = 294 K |
V = 1354.1 (3) Å3 | Plate, colourless |
Z = 2 | 0.42 × 0.35 × 0.25 mm |
Enraf-Nonius CAD-4 diffractometer | 2431 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.008 |
Graphite monochromator | θmax = 27.4°, θmin = 2.3° |
θ/2θ scans | h = −10→10 |
Absorption correction: gaussian ABSO in NRCVAX (Gabe et al., 1989) | k = 0→23 |
Tmin = 0.915, Tmax = 0.951 | l = 0→12 |
3271 measured reflections | 3 standard reflections every 240 min |
3102 independent reflections | intensity decay: no decay, variation 1.0% |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.04 | Calculated w = 1/[σ2(Fo2) + (0.0514P)2 + 0.2603P] where P = (Fo2 + 2Fc2)/3 |
3102 reflections | (Δ/σ)max < 0.001 |
183 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
2(C12H10O4S)·C4H4N2 | V = 1354.1 (3) Å3 |
Mr = 580.64 | Z = 2 |
Monoclinic, P21/a | Mo Kα radiation |
a = 8.3506 (9) Å | µ = 0.25 mm−1 |
b = 18.0102 (17) Å | T = 294 K |
c = 9.6360 (14) Å | 0.42 × 0.35 × 0.25 mm |
β = 110.869 (8)° |
Enraf-Nonius CAD-4 diffractometer | 2431 reflections with I > 2σ(I) |
Absorption correction: gaussian ABSO in NRCVAX (Gabe et al., 1989) | Rint = 0.008 |
Tmin = 0.915, Tmax = 0.951 | 3 standard reflections every 240 min |
3271 measured reflections | intensity decay: no decay, variation 1.0% |
3102 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.25 e Å−3 |
3102 reflections | Δρmin = −0.22 e Å−3 |
183 parameters |
Experimental. ? #Insert any special details here. |
Geometry. Data from SHELXL "MPLA" calculations: Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 3.6443 (68) x + 11.1282 (149) y + 7.3869 (61) z = 10.2386 (143) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 7.7294 (26) x + 6.2158 (100) y - 1.7785 (58) z = 8.3599 (92) Angle to previous plane (with approximate e.s.d.) = 84.89 (6) * 0.0173 (0.0013) C11 * 0.0230 (0.0013) C12 * 0.0168 (0.0014) C13 * -0.0075 (0.0015) C14 * 0.0147 (0.0014) C15 * 0.0217 (0.0014) C16 * -0.0475 (0.0008) S1 * -0.0386 (0.0012) O14 Rms deviation of fitted atoms = 0.0265 - 3.6443 (68) x + 11.1282 (149) y + 7.3869 (61) z = 10.2386 (143) Angle to previous plane (with approximate e.s.d.) = 84.89 (6) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 0.7837 (30) x + 11.9096 (88) y - 7.0233 (46) z = 10.1779 (81) Angle to previous plane (with approximate e.s.d.) = 83.16 (5) * 0.0168 (0.0012) C21 * 0.0203 (0.0011) C22 * 0.0202 (0.0012) C23 * -0.0041 (0.0013) C24 * 0.0146 (0.0013) C25 * 0.0282 (0.0013) C26 * -0.0513 (0.0008) S1 * -0.0448 (0.0010) O24 Rms deviation of fitted atoms = 0.0291 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.36932 (5) | 0.92714 (2) | 0.17153 (5) | 0.04010 (13) | |
O11 | 0.38809 (15) | 0.99950 (6) | 0.23802 (15) | 0.0559 (3) | |
O12 | 0.43825 (16) | 0.91427 (8) | 0.05627 (15) | 0.0584 (4) | |
O14 | 0.6544 (2) | 0.71281 (7) | 0.65639 (14) | 0.0660 (4) | |
O24 | −0.35317 (14) | 0.83936 (7) | −0.05886 (14) | 0.0514 (3) | |
C11 | 0.46227 (18) | 0.86282 (8) | 0.31429 (17) | 0.0364 (3) | |
C12 | 0.4813 (2) | 0.88156 (9) | 0.45905 (18) | 0.0429 (4) | |
C13 | 0.5472 (2) | 0.83100 (9) | 0.5723 (2) | 0.0478 (4) | |
C14 | 0.5934 (2) | 0.76059 (9) | 0.54101 (19) | 0.0453 (4) | |
C15 | 0.5778 (2) | 0.74230 (9) | 0.3968 (2) | 0.0519 (4) | |
C16 | 0.5119 (2) | 0.79304 (9) | 0.28341 (19) | 0.0474 (4) | |
C21 | 0.15116 (18) | 0.90416 (8) | 0.09853 (16) | 0.0341 (3) | |
C22 | 0.03652 (19) | 0.94115 (9) | 0.14798 (17) | 0.0381 (3) | |
C23 | −0.13372 (19) | 0.92083 (9) | 0.09453 (17) | 0.0393 (3) | |
C24 | −0.18836 (19) | 0.86301 (9) | −0.00616 (16) | 0.0376 (3) | |
C25 | −0.0738 (2) | 0.82674 (9) | −0.05755 (19) | 0.0435 (4) | |
C26 | 0.0959 (2) | 0.84748 (9) | −0.00537 (18) | 0.0425 (4) | |
N1 | 0.5778 (2) | 0.56714 (8) | 0.55556 (18) | 0.0539 (4) | |
C2 | 0.4100 (2) | 0.56163 (10) | 0.4824 (2) | 0.0560 (5) | |
C6 | 0.6667 (2) | 0.50485 (11) | 0.5726 (2) | 0.0539 (5) | |
H14 | 0.6463 | 0.6702 | 0.6248 | 0.099* | |
H24 | −0.4094 | 0.8634 | −0.0201 | 0.077* | |
H12 | 0.4492 | 0.9286 | 0.4796 | 0.051* | |
H13 | 0.5607 | 0.8439 | 0.6693 | 0.057* | |
H15 | 0.6120 | 0.6957 | 0.3766 | 0.062* | |
H16 | 0.5007 | 0.7806 | 0.1867 | 0.057* | |
H22 | 0.0740 | 0.9794 | 0.2168 | 0.046* | |
H23 | −0.2119 | 0.9459 | 0.1261 | 0.047* | |
H25 | −0.1115 | 0.7887 | −0.1268 | 0.052* | |
H26 | 0.1734 | 0.8236 | −0.0396 | 0.051* | |
H2 | 0.3426 | 0.6041 | 0.4679 | 0.067* | |
H6 | 0.7845 | 0.5062 | 0.6232 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02949 (19) | 0.0406 (2) | 0.0475 (2) | −0.00094 (15) | 0.01038 (16) | 0.00472 (17) |
O11 | 0.0439 (7) | 0.0367 (6) | 0.0724 (8) | −0.0039 (5) | 0.0028 (6) | 0.0021 (6) |
O12 | 0.0420 (6) | 0.0789 (9) | 0.0612 (8) | 0.0045 (6) | 0.0268 (6) | 0.0168 (7) |
O14 | 0.0895 (11) | 0.0456 (7) | 0.0473 (7) | 0.0030 (7) | 0.0052 (7) | 0.0045 (6) |
O24 | 0.0338 (6) | 0.0634 (8) | 0.0546 (7) | −0.0094 (5) | 0.0130 (5) | −0.0065 (6) |
C11 | 0.0284 (7) | 0.0367 (7) | 0.0400 (8) | 0.0014 (6) | 0.0070 (6) | −0.0016 (6) |
C12 | 0.0416 (8) | 0.0375 (8) | 0.0464 (9) | 0.0020 (6) | 0.0118 (7) | −0.0082 (7) |
C13 | 0.0542 (10) | 0.0463 (9) | 0.0380 (8) | −0.0003 (8) | 0.0106 (7) | −0.0072 (7) |
C14 | 0.0447 (9) | 0.0392 (8) | 0.0424 (9) | −0.0012 (7) | 0.0039 (7) | −0.0003 (7) |
C15 | 0.0619 (11) | 0.0374 (8) | 0.0504 (10) | 0.0115 (8) | 0.0125 (8) | −0.0058 (7) |
C16 | 0.0534 (10) | 0.0452 (9) | 0.0395 (8) | 0.0075 (7) | 0.0113 (7) | −0.0070 (7) |
C21 | 0.0286 (7) | 0.0366 (7) | 0.0347 (7) | 0.0013 (6) | 0.0084 (6) | 0.0021 (6) |
C22 | 0.0368 (8) | 0.0414 (8) | 0.0340 (7) | 0.0005 (6) | 0.0102 (6) | −0.0050 (6) |
C23 | 0.0340 (7) | 0.0494 (9) | 0.0351 (8) | 0.0051 (6) | 0.0131 (6) | −0.0008 (7) |
C24 | 0.0321 (7) | 0.0440 (8) | 0.0334 (7) | −0.0013 (6) | 0.0076 (6) | 0.0059 (6) |
C25 | 0.0413 (8) | 0.0428 (8) | 0.0429 (9) | −0.0023 (7) | 0.0105 (7) | −0.0103 (7) |
C26 | 0.0370 (8) | 0.0466 (9) | 0.0449 (9) | 0.0054 (6) | 0.0158 (7) | −0.0052 (7) |
N1 | 0.0510 (9) | 0.0475 (8) | 0.0582 (9) | 0.0007 (7) | 0.0133 (7) | 0.0091 (7) |
C2 | 0.0482 (10) | 0.0464 (10) | 0.0712 (12) | 0.0123 (8) | 0.0188 (9) | 0.0132 (9) |
C6 | 0.0381 (8) | 0.0579 (10) | 0.0601 (11) | 0.0045 (8) | 0.0106 (8) | 0.0193 (9) |
S1—O11 | 1.4360 (13) | C15—C16 | 1.380 (2) |
S1—O12 | 1.4401 (13) | C21—C22 | 1.383 (2) |
S1—C21 | 1.7527 (15) | C21—C26 | 1.389 (2) |
S1—C11 | 1.7539 (15) | C22—C23 | 1.378 (2) |
O14—C14 | 1.354 (2) | C23—C24 | 1.385 (2) |
O24—C24 | 1.3548 (18) | C24—C25 | 1.387 (2) |
C11—C16 | 1.388 (2) | C25—C26 | 1.376 (2) |
C11—C12 | 1.388 (2) | N1—C6 | 1.323 (2) |
C12—C13 | 1.377 (2) | N1—C2 | 1.329 (2) |
C13—C14 | 1.390 (2) | C2—C6i | 1.372 (3) |
C14—C15 | 1.388 (2) | C6—C2i | 1.372 (3) |
O11—S1—O12 | 118.69 (8) | C15—C16—C11 | 119.69 (15) |
O11—S1—C21 | 109.03 (7) | C22—C21—C26 | 120.64 (14) |
O12—S1—C21 | 107.24 (8) | C22—C21—S1 | 119.74 (12) |
O11—S1—C11 | 107.58 (7) | C26—C21—S1 | 119.59 (11) |
O12—S1—C11 | 108.17 (8) | C23—C22—C21 | 119.47 (14) |
C21—S1—C11 | 105.37 (7) | C22—C23—C24 | 120.00 (14) |
C16—C11—C12 | 119.97 (15) | O24—C24—C23 | 122.41 (14) |
C16—C11—S1 | 120.81 (12) | O24—C24—C25 | 117.12 (14) |
C12—C11—S1 | 119.19 (12) | C23—C24—C25 | 120.47 (14) |
C13—C12—C11 | 120.41 (15) | C26—C25—C24 | 119.55 (15) |
C12—C13—C14 | 119.65 (16) | C25—C26—C21 | 119.83 (14) |
O14—C14—C15 | 123.03 (15) | C6—N1—C2 | 116.18 (16) |
O14—C14—C13 | 116.99 (16) | N1—C2—C6i | 121.92 (16) |
C15—C14—C13 | 119.98 (16) | N1—C6—C2i | 121.91 (17) |
C16—C15—C14 | 120.27 (15) | ||
O11—S1—C11—C16 | −159.94 (13) | O12—S1—C21—C22 | −149.18 (13) |
O12—S1—C11—C16 | −30.60 (16) | C11—S1—C21—C22 | 95.74 (13) |
C21—S1—C11—C16 | 83.84 (15) | O11—S1—C21—C26 | 162.34 (13) |
O11—S1—C11—C12 | 22.02 (15) | O12—S1—C21—C26 | 32.65 (15) |
O12—S1—C11—C12 | 151.36 (13) | C11—S1—C21—C26 | −82.43 (14) |
C21—S1—C11—C12 | −94.21 (14) | C26—C21—C22—C23 | 0.7 (2) |
C16—C11—C12—C13 | −0.8 (2) | S1—C21—C22—C23 | −177.44 (12) |
S1—C11—C12—C13 | 177.27 (13) | C21—C22—C23—C24 | 1.0 (2) |
C11—C12—C13—C14 | −0.6 (3) | C22—C23—C24—O24 | 178.02 (14) |
C12—C13—C14—O14 | −178.76 (16) | C22—C23—C24—C25 | −2.1 (2) |
C12—C13—C14—C15 | 1.9 (3) | O24—C24—C25—C26 | −178.68 (15) |
O14—C14—C15—C16 | 178.83 (17) | C23—C24—C25—C26 | 1.4 (2) |
C13—C14—C15—C16 | −1.9 (3) | C24—C25—C26—C21 | 0.3 (3) |
C14—C15—C16—C11 | 0.5 (3) | C22—C21—C26—C25 | −1.4 (2) |
C12—C11—C16—C15 | 0.8 (3) | S1—C21—C26—C25 | 176.78 (13) |
S1—C11—C16—C15 | −177.21 (14) | C6—N1—C2—C6i | −0.1 (3) |
O11—S1—C21—C22 | −19.49 (15) | C2—N1—C6—C2i | 0.1 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N1 | 0.82 | 1.99 | 2.792 (2) | 167 |
O24—H24···O12ii | 0.82 | 1.91 | 2.732 (2) | 174 |
C6—H6···O11iii | 0.93 | 2.58 | 3.511 (2) | 176 |
C12—H12···O11 | 0.93 | 2.54 | 2.911 (2) | 104 |
C13—H13···O24iv | 0.93 | 2.46 | 3.353 (2) | 161 |
C22—H22···O11 | 0.93 | 2.58 | 2.943 (2) | 104 |
Symmetry codes: (ii) x−1, y, z; (iii) −x+3/2, y−1/2, −z+1; (iv) x+1, y, z+1. |
C12H10O4S·C10H8N2 | F(000) = 848 |
Mr = 406.44 | ? #Insert any comments here. |
Monoclinic, P21/n | Dx = 1.380 Mg m−3 |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.7107 Å |
a = 7.5765 (10) Å | Cell parameters from 25 reflections |
b = 23.9154 (10) Å | θ = 9.5–18.8° |
c = 11.225 (2) Å | µ = 0.20 mm−1 |
β = 105.921 (10)° | T = 294 K |
V = 1955.9 (4) Å3 | Needle, colourless |
Z = 4 | 0.42 × 0.22 × 0.18 mm |
Enraf-Nonius CAD-4 diffractometer | 2461 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.011 |
Graphite monochromator | θmax = 25.1°, θmin = 2.1° |
θ/2θ scans | h = −9→8 |
Absorption correction: gaussian ABSO in NRCVAX96 (Gabe et al., 1989) | k = 0→28 |
Tmin = 0.952, Tmax = 0.971 | l = 0→13 |
3774 measured reflections | 3 standard reflections every 120 min |
3504 independent reflections | intensity decay: no decay, variation 0.6% |
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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.098 | Calculated w = 1/[σ2(Fo2) + (0.0495P)2 + 0.0855P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3504 reflections | Δρmax = 0.23 e Å−3 |
265 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0043 (9) |
C12H10O4S·C10H8N2 | V = 1955.9 (4) Å3 |
Mr = 406.44 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.5765 (10) Å | µ = 0.20 mm−1 |
b = 23.9154 (10) Å | T = 294 K |
c = 11.225 (2) Å | 0.42 × 0.22 × 0.18 mm |
β = 105.921 (10)° |
Enraf-Nonius CAD-4 diffractometer | 2461 reflections with I > 2σ(I) |
Absorption correction: gaussian ABSO in NRCVAX96 (Gabe et al., 1989) | Rint = 0.011 |
Tmin = 0.952, Tmax = 0.971 | 3 standard reflections every 120 min |
3774 measured reflections | intensity decay: no decay, variation 0.6% |
3504 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.23 e Å−3 |
3504 reflections | Δρmin = −0.25 e Å−3 |
265 parameters |
Experimental. ? #Insert any special details here. |
Geometry. Mean plane details ex last SHELXL97 run Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.3860 (0.0019) x + 3.7745 (0.0288) y - 4.7001 (0.0081) z = 3.0802 (0.0047) * 0.0127 (0.0019) N31 * -0.0068 (0.0021) C32 * -0.0049 (0.0021) C33 * -0.0012 (0.0020) C34 * -0.0170 (0.0022) C35 * 0.0056 (0.0020) C36 * 0.0115 (0.0014) C44 Rms deviation of fitted atoms = 0.0099 6.9788 (0.0031) x - 5.5098 (0.0246) y - 6.2238 (0.0060) z = 2.2149 (0.0066) Angle to previous plane (with approximate e.s.d.) = 24.36 (6) * -0.0033 (0.0017) N41 * 0.0018 (0.0017) C42 * 0.0021 (0.0019) C43 * -0.0044 (0.0019) C44 * 0.0029 (0.0018) C45 * 0.0009 (0.0017) C46 * 0.0001 (0.0013) C34 Rms deviation of fitted atoms = 0.0026 5.6319 (0.0068) x + 3.9321 (0.0244) y + 4.7102 (0.0140) z = 3.5619 (0.0071) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 1.1941 (0.0055) x + 20.0164 (0.0072) y - 6.1423 (0.0047) z = 5.9051 (0.0040) Angle to previous plane (with approximate e.s.d.) = 85.12 (7) * 0.0694 (0.0017) C21 * 0.0508 (0.0016) C22 * 0.0173 (0.0017) C23 * -0.0149 (0.0018) C24 * 0.0144 (0.0017) C25 * 0.0551 (0.0016) C26 * -0.1181 (0.0010) S1 * -0.0739 (0.0013) O24 Rms deviation of fitted atoms = 0.0618 5.6319 (0.0068) x + 3.9321 (0.0244) y + 4.7102 (0.0140) z = 3.5619 (0.0071) Angle to previous plane (with approximate e.s.d.) = 85.12 (7) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 7.0510 (0.0028) x - 6.4997 (0.0108) y - 5.5105 (0.0083) z = 2.1951 (0.0031) Angle to previous plane (with approximate e.s.d.) = 60.78 (7) * 0.0056 (0.0017) C11 * 0.0050 (0.0017) C12 * -0.0033 (0.0018) C13 * -0.0048 (0.0019) C14 * 0.0056 (0.0017) C15 * -0.0038 (0.0016) C16 * -0.0043 (0.0010) S1 * 0.0001 (0.0014) O14 Rms deviation of fitted atoms = 0.0044 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.50024 (8) | 0.24501 (2) | −0.04646 (5) | 0.03750 (17) | |
O11 | 0.6892 (2) | 0.26237 (6) | −0.02331 (14) | 0.0484 (4) | |
O12 | 0.3867 (2) | 0.24369 (6) | −0.17218 (13) | 0.0478 (4) | |
O14 | 0.4628 (3) | 0.02237 (6) | 0.16747 (14) | 0.0576 (5) | |
O24 | 0.1492 (2) | 0.36777 (8) | 0.27812 (14) | 0.0578 (5) | |
C11 | 0.4917 (3) | 0.17847 (8) | 0.01930 (17) | 0.0344 (5) | |
C12 | 0.5800 (3) | 0.16908 (9) | 0.14344 (18) | 0.0424 (5) | |
C13 | 0.5713 (3) | 0.11760 (9) | 0.19461 (19) | 0.0441 (6) | |
C14 | 0.4748 (3) | 0.07416 (8) | 0.12264 (18) | 0.0388 (5) | |
C15 | 0.3884 (3) | 0.08386 (9) | −0.00124 (19) | 0.0432 (5) | |
C16 | 0.3947 (3) | 0.13566 (8) | −0.05259 (18) | 0.0380 (5) | |
C21 | 0.3963 (3) | 0.28776 (8) | 0.04213 (18) | 0.0369 (5) | |
C22 | 0.5046 (3) | 0.31290 (9) | 0.14813 (19) | 0.0412 (5) | |
C23 | 0.4241 (3) | 0.34028 (9) | 0.2271 (2) | 0.0451 (6) | |
C24 | 0.2343 (3) | 0.34222 (9) | 0.20179 (19) | 0.0418 (5) | |
C25 | 0.1260 (3) | 0.31734 (9) | 0.0949 (2) | 0.0468 (6) | |
C26 | 0.2065 (3) | 0.29020 (9) | 0.0155 (2) | 0.0429 (5) | |
N31 | 0.6742 (3) | −0.00330 (8) | 0.39881 (17) | 0.0543 (5) | |
C32 | 0.7099 (4) | −0.05730 (10) | 0.4157 (2) | 0.0626 (7) | |
C33 | 0.7944 (4) | −0.08108 (10) | 0.5289 (2) | 0.0574 (7) | |
C34 | 0.8442 (3) | −0.04787 (8) | 0.63313 (19) | 0.0411 (5) | |
C35 | 0.8023 (4) | 0.00828 (9) | 0.6157 (2) | 0.0584 (7) | |
C36 | 0.7209 (4) | 0.02832 (10) | 0.4990 (2) | 0.0626 (7) | |
N41 | 1.1158 (3) | −0.11110 (8) | 0.99419 (17) | 0.0502 (5) | |
C42 | 1.1305 (3) | −0.05829 (10) | 0.9630 (2) | 0.0507 (6) | |
C43 | 1.0455 (3) | −0.03670 (9) | 0.8486 (2) | 0.0506 (6) | |
C44 | 0.9369 (3) | −0.07054 (8) | 0.75781 (19) | 0.0393 (5) | |
C45 | 0.9223 (3) | −0.12621 (9) | 0.7896 (2) | 0.0487 (6) | |
C46 | 1.0126 (3) | −0.14408 (10) | 0.9069 (2) | 0.0537 (6) | |
H14 | 0.5314 | 0.0200 | 0.2379 | 0.086* | |
H24 | 0.2235 | 0.3736 | 0.3453 | 0.087* | |
H12 | 0.6451 | 0.1978 | 0.1919 | 0.051* | |
H13 | 0.6302 | 0.1115 | 0.2779 | 0.053* | |
H15 | 0.3254 | 0.0549 | −0.0502 | 0.052* | |
H16 | 0.3340 | 0.1420 | −0.1355 | 0.046* | |
H22 | 0.6319 | 0.3113 | 0.1658 | 0.049* | |
H23 | 0.4969 | 0.3576 | 0.2978 | 0.054* | |
H25 | −0.0012 | 0.3191 | 0.0771 | 0.056* | |
H26 | 0.1338 | 0.2735 | −0.0560 | 0.052* | |
H32 | 0.6760 | −0.0807 | 0.3470 | 0.075* | |
H33 | 0.8176 | −0.1193 | 0.5349 | 0.069* | |
H35 | 0.8293 | 0.0325 | 0.6831 | 0.070* | |
H36 | 0.6971 | 0.0665 | 0.4899 | 0.075* | |
H42 | 1.2026 | −0.0345 | 1.0222 | 0.061* | |
H43 | 1.0610 | 0.0008 | 0.8320 | 0.061* | |
H45 | 0.8523 | −0.1511 | 0.7321 | 0.058* | |
H46 | 1.0008 | −0.1814 | 0.9265 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0405 (3) | 0.0362 (3) | 0.0330 (3) | 0.0015 (2) | 0.0054 (2) | 0.0021 (2) |
O11 | 0.0417 (9) | 0.0518 (9) | 0.0530 (9) | −0.0064 (7) | 0.0155 (7) | −0.0002 (7) |
O12 | 0.0571 (10) | 0.0469 (9) | 0.0329 (8) | 0.0058 (8) | 0.0013 (7) | 0.0034 (6) |
O14 | 0.0734 (13) | 0.0406 (9) | 0.0481 (10) | −0.0083 (8) | −0.0015 (9) | 0.0071 (7) |
O24 | 0.0477 (11) | 0.0752 (11) | 0.0498 (10) | 0.0038 (9) | 0.0123 (8) | −0.0154 (9) |
C11 | 0.0324 (12) | 0.0349 (10) | 0.0327 (11) | 0.0047 (9) | 0.0037 (9) | −0.0011 (8) |
C12 | 0.0481 (14) | 0.0386 (12) | 0.0326 (11) | −0.0012 (10) | −0.0021 (10) | −0.0041 (9) |
C13 | 0.0524 (15) | 0.0428 (12) | 0.0299 (11) | 0.0039 (11) | −0.0009 (10) | 0.0022 (9) |
C14 | 0.0417 (13) | 0.0360 (11) | 0.0361 (11) | 0.0018 (10) | 0.0059 (10) | 0.0032 (9) |
C15 | 0.0430 (14) | 0.0404 (12) | 0.0396 (12) | −0.0064 (10) | 0.0000 (10) | −0.0031 (9) |
C16 | 0.0359 (12) | 0.0437 (12) | 0.0293 (10) | 0.0000 (10) | 0.0001 (9) | −0.0006 (9) |
C21 | 0.0380 (13) | 0.0324 (11) | 0.0362 (11) | 0.0008 (9) | 0.0034 (9) | 0.0012 (8) |
C22 | 0.0334 (12) | 0.0433 (12) | 0.0429 (12) | 0.0002 (10) | 0.0036 (10) | −0.0033 (10) |
C23 | 0.0396 (14) | 0.0482 (13) | 0.0420 (12) | −0.0047 (11) | 0.0019 (10) | −0.0120 (10) |
C24 | 0.0454 (15) | 0.0382 (12) | 0.0411 (12) | 0.0025 (10) | 0.0110 (10) | −0.0012 (9) |
C25 | 0.0326 (13) | 0.0533 (14) | 0.0499 (14) | 0.0028 (11) | 0.0036 (11) | −0.0046 (11) |
C26 | 0.0390 (13) | 0.0420 (12) | 0.0408 (12) | −0.0012 (10) | −0.0008 (10) | −0.0064 (10) |
N31 | 0.0608 (14) | 0.0507 (12) | 0.0445 (11) | 0.0019 (10) | 0.0030 (10) | 0.0062 (9) |
C32 | 0.083 (2) | 0.0516 (15) | 0.0423 (14) | 0.0033 (14) | −0.0004 (14) | −0.0060 (11) |
C33 | 0.0735 (19) | 0.0397 (13) | 0.0501 (14) | 0.0057 (12) | 0.0019 (13) | −0.0033 (10) |
C34 | 0.0373 (13) | 0.0402 (12) | 0.0430 (12) | −0.0004 (10) | 0.0066 (10) | 0.0017 (9) |
C35 | 0.0802 (19) | 0.0402 (13) | 0.0458 (13) | 0.0058 (13) | 0.0020 (13) | −0.0015 (10) |
C36 | 0.083 (2) | 0.0421 (13) | 0.0532 (15) | 0.0066 (13) | 0.0017 (14) | 0.0080 (11) |
N41 | 0.0454 (12) | 0.0589 (12) | 0.0458 (11) | 0.0037 (10) | 0.0116 (10) | 0.0107 (10) |
C42 | 0.0501 (15) | 0.0551 (15) | 0.0424 (13) | −0.0004 (12) | 0.0048 (11) | −0.0032 (11) |
C43 | 0.0524 (15) | 0.0416 (12) | 0.0503 (13) | −0.0017 (11) | 0.0016 (12) | 0.0024 (11) |
C44 | 0.0358 (12) | 0.0410 (12) | 0.0401 (12) | 0.0032 (10) | 0.0087 (10) | 0.0017 (9) |
C45 | 0.0496 (15) | 0.0439 (12) | 0.0483 (13) | −0.0031 (11) | 0.0062 (11) | 0.0002 (10) |
C46 | 0.0590 (17) | 0.0453 (13) | 0.0546 (15) | −0.0038 (12) | 0.0117 (13) | 0.0126 (11) |
S1—O11 | 1.4438 (15) | C24—C25 | 1.388 (3) |
S1—O12 | 1.4377 (15) | C25—C26 | 1.373 (3) |
S1—C11 | 1.7628 (19) | N31—C32 | 1.322 (3) |
S1—C21 | 1.756 (2) | N31—C36 | 1.320 (3) |
O14—C14 | 1.349 (2) | C32—C33 | 1.379 (3) |
O24—C24 | 1.351 (3) | C33—C34 | 1.378 (3) |
C11—C12 | 1.389 (3) | C34—C35 | 1.381 (3) |
C11—C16 | 1.384 (3) | C34—C44 | 1.485 (3) |
C12—C13 | 1.368 (3) | C35—C36 | 1.372 (3) |
C13—C14 | 1.394 (3) | N41—C42 | 1.323 (3) |
C14—C15 | 1.384 (3) | N41—C46 | 1.332 (3) |
C15—C16 | 1.373 (3) | C42—C43 | 1.370 (3) |
C21—C22 | 1.384 (3) | C43—C44 | 1.383 (3) |
C21—C26 | 1.388 (3) | C44—C45 | 1.391 (3) |
C22—C23 | 1.373 (3) | C45—C46 | 1.375 (3) |
C23—C24 | 1.388 (3) | ||
O11—S1—O12 | 118.68 (10) | O24—C24—C25 | 118.1 (2) |
O12—S1—C21 | 109.15 (9) | O24—C24—C23 | 122.2 (2) |
O11—S1—C21 | 107.89 (10) | C23—C24—C25 | 119.8 (2) |
O12—S1—C11 | 108.08 (9) | C24—C25—C26 | 120.1 (2) |
O11—S1—C11 | 109.42 (9) | C21—C26—C25 | 119.9 (2) |
C11—S1—C21 | 102.40 (9) | C32—N31—C36 | 116.2 (2) |
C12—C11—C16 | 119.87 (18) | N31—C32—C33 | 124.1 (2) |
S1—C11—C16 | 119.90 (15) | C32—C33—C34 | 119.6 (2) |
S1—C11—C12 | 120.23 (15) | C33—C34—C35 | 116.2 (2) |
C11—C12—C13 | 120.12 (19) | C33—C34—C44 | 122.55 (19) |
C12—C13—C14 | 120.36 (19) | C35—C34—C44 | 121.3 (2) |
O14—C14—C15 | 117.83 (18) | C34—C35—C36 | 120.0 (2) |
O14—C14—C13 | 123.12 (18) | N31—C36—C35 | 123.9 (2) |
C13—C14—C15 | 119.05 (19) | C42—N41—C46 | 116.5 (2) |
C14—C15—C16 | 120.79 (19) | N41—C42—C43 | 123.7 (2) |
C11—C16—C15 | 119.80 (18) | C42—C43—C44 | 120.2 (2) |
C22—C21—C26 | 120.2 (2) | C43—C44—C45 | 116.4 (2) |
S1—C21—C22 | 119.17 (17) | C34—C44—C43 | 120.87 (19) |
S1—C21—C26 | 120.11 (16) | C34—C44—C45 | 122.75 (19) |
C21—C22—C23 | 119.9 (2) | C44—C45—C46 | 119.3 (2) |
C22—C23—C24 | 120.2 (2) | N41—C46—C45 | 123.9 (2) |
O12—S1—C11—C16 | 3.4 (2) | C22—C23—C24—C25 | −1.3 (3) |
O11—S1—C11—C16 | −127.14 (18) | O24—C24—C25—C26 | −179.1 (2) |
C21—S1—C11—C16 | 118.59 (18) | C23—C24—C25—C26 | 1.0 (3) |
O12—S1—C11—C12 | −175.72 (17) | C24—C25—C26—C21 | −0.1 (3) |
O11—S1—C11—C12 | 53.7 (2) | C22—C21—C26—C25 | −0.4 (3) |
C21—S1—C11—C12 | −60.6 (2) | S1—C21—C26—C25 | 170.95 (17) |
C16—C11—C12—C13 | 0.1 (3) | C36—N31—C32—C33 | −1.4 (4) |
S1—C11—C12—C13 | 179.23 (18) | N31—C32—C33—C34 | 0.9 (4) |
C11—C12—C13—C14 | 0.3 (4) | C32—C33—C34—C35 | 0.8 (4) |
C12—C13—C14—O14 | 179.3 (2) | C32—C33—C34—C44 | −179.5 (2) |
C12—C13—C14—C15 | 0.2 (3) | C33—C34—C35—C36 | −2.0 (4) |
O14—C14—C15—C16 | 179.8 (2) | C44—C34—C35—C36 | 178.4 (2) |
C13—C14—C15—C16 | −1.0 (3) | C32—N31—C36—C35 | 0.2 (4) |
C14—C15—C16—C11 | 1.4 (3) | C34—C35—C36—N31 | 1.6 (4) |
C12—C11—C16—C15 | −0.9 (3) | C46—N41—C42—C43 | 0.4 (4) |
S1—C11—C16—C15 | 179.92 (17) | N41—C42—C43—C44 | 0.1 (4) |
O12—S1—C21—C22 | −155.04 (16) | C42—C43—C44—C45 | −0.6 (3) |
O11—S1—C21—C22 | −24.81 (19) | C42—C43—C44—C34 | −179.8 (2) |
C11—S1—C21—C22 | 90.58 (18) | C33—C34—C44—C43 | 155.1 (2) |
O12—S1—C21—C26 | 33.5 (2) | C35—C34—C44—C43 | −25.2 (3) |
O11—S1—C21—C26 | 163.77 (17) | C33—C34—C44—C45 | −24.0 (4) |
C11—S1—C21—C26 | −80.83 (18) | C35—C34—C44—C45 | 155.6 (2) |
C26—C21—C22—C23 | 0.0 (3) | C43—C44—C45—C46 | 0.7 (3) |
S1—C21—C22—C23 | −171.37 (16) | C34—C44—C45—C46 | 179.9 (2) |
C21—C22—C23—C24 | 0.8 (3) | C42—N41—C46—C45 | −0.4 (4) |
C22—C23—C24—O24 | 178.7 (2) | C44—C45—C46—N41 | −0.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N31 | 0.82 | 1.92 | 2.721 (3) | 167 |
O24—H24···N41i | 0.82 | 1.91 | 2.731 (3) | 176 |
C12—H12···O12ii | 0.93 | 2.47 | 3.376 (3) | 165 |
C42—H42···O14iii | 0.93 | 2.58 | 3.487 (3) | 167 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x+1, y, z+1. |
C12H10O4S·C12H10N2 | F(000) = 452 |
Mr = 432.48 | ? #Insert any comments here. |
Triclinic, P1 | Dx = 1.347 Mg m−3 |
a = 7.3981 (8) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 12.7472 (15) Å | Cell parameters from 25 reflections |
c = 13.0006 (13) Å | θ = 9.9–18.2° |
α = 115.037 (8)° | µ = 0.19 mm−1 |
β = 102.398 (10)° | T = 294 K |
γ = 94.239 (10)° | Needle, colourless |
V = 1065.9 (2) Å3 | 0.42 × 0.28 × 0.24 mm |
Z = 2 |
Enraf-Nonius CAD-4 diffractometer | 2948 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.000 |
Graphite monochromator | θmax = 25.2°, θmin = 2.9° |
θ/2θ scans | h = −8→8 |
Absorption correction: gaussian ABSO in NRCVAX (Gabe et al., 1989) | k = 0→15 |
Tmin = 0.949, Tmax = 0.967 | l = −15→14 |
3829 measured reflections | 3 standard reflections every 120 min |
3829 independent reflections | intensity decay: no decay, variation 1.0% |
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)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.100 | Calculated w = 1/[σ2(Fo2) + (0.0529P)2 + 0.2472P] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.001 |
3829 reflections | Δρmax = 0.21 e Å−3 |
330 parameters | Δρmin = −0.20 e Å−3 |
41 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0143 (18) |
C12H10O4S·C12H10N2 | γ = 94.239 (10)° |
Mr = 432.48 | V = 1065.9 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.3981 (8) Å | Mo Kα radiation |
b = 12.7472 (15) Å | µ = 0.19 mm−1 |
c = 13.0006 (13) Å | T = 294 K |
α = 115.037 (8)° | 0.42 × 0.28 × 0.24 mm |
β = 102.398 (10)° |
Enraf-Nonius CAD-4 diffractometer | 2948 reflections with I > 2σ(I) |
Absorption correction: gaussian ABSO in NRCVAX (Gabe et al., 1989) | Rint = 0.000 |
Tmin = 0.949, Tmax = 0.967 | 3 standard reflections every 120 min |
3829 measured reflections | intensity decay: no decay, variation 1.0% |
3829 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 41 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.21 e Å−3 |
3829 reflections | Δρmin = −0.20 e Å−3 |
330 parameters |
Experimental. ? #Insert any special details here. |
Geometry. Mean-plane calculations ex the final SHELXL run. The symmetry transformations are defined by:- $1 = -x, -y, -z $2 = 1 - x, 1 - y, 2 - z ################################## Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.2237 (0.0018) x - 0.1035 (0.0098) y - 5.4285 (0.0095) z = 1.7118 (0.0053) * 0.0117 (0.0012) C11 * -0.0050 (0.0013) C12 * -0.0072 (0.0013) C13 * 0.0127 (0.0013) C14 * -0.0062 (0.0014) C15 * -0.0060 (0.0014) C16 - 3.4348 (0.0079) N41_$1 - 3.7468 (0.0062) C42_$1 - 3.8333 (0.0036) C43_$1 - 3.6297 (0.0033) C44_$1 - 3.3299 (0.0039) C45_$1 - 3.2215 (0.0048) C46_$1 Rms deviation of fitted atoms = 0.0087 ############################## - 6.8848 (0.0062) x - 2.8713 (0.0253) y + 6.7430 (0.0270) z = 1.9027 (0.0122) Angle to previous plane (with approximate e.s.d.) = 13.52 (13) * -0.0004 (0.0039) N41_$1 * 0.0100 (0.0040) C42_$1 * -0.0084 (0.0027) C43_$1 * -0.0021 (0.0023) C44_$1 * 0.0112 (0.0023) C45_$1 * -0.0103 (0.0027) C46_$1 - 3.7399 (0.0075) C11 - 3.4054 (0.0086) C12 - 3.1973 (0.0072) C13 - 3.3263 (0.0045) C14 - 3.6269 (0.0030) C15 - 3.8322 (0.0049) C16 Rms deviation of fitted atoms = 0.0082 ############################## 7.2237 (0.0018) x - 0.1035 (0.0098) y - 5.4285 (0.0095) z = 1.7118 (0.0053) Angle to previous plane (with approximate e.s.d.) = 13.52 (13) * 0.0117 (0.0012) C11 * -0.0050 (0.0013) C12 * -0.0072 (0.0013) C13 * 0.0127 (0.0013) C14 * -0.0062 (0.0014) C15 * -0.0060 (0.0014) C16 - 3.5173 (0.0291) N61_$1 - 3.4051 (0.0178) C62_$1 - 3.4304 (0.0131) C63_$1 - 3.5954 (0.0104) C64_$1 - 3.7213 (0.0161) C65_$1 - 3.6652 (0.0253) C66_$1 Rms deviation of fitted atoms = 0.0087 ############################## - 7.0717 (0.0205) x - 1.4387 (0.1093) y + 6.3165 (0.1099) z = 2.0307 (0.0482) Angle to previous plane (with approximate e.s.d.) = 7.1 (5) * 0.0014 (0.0130) N61_$1 * 0.0042 (0.0068) C62_$1 * -0.0045 (0.0087) C63_$1 * -0.0004 (0.0104) C64_$1 * 0.0057 (0.0127) C65_$1 * -0.0064 (0.0162) C66_$1 - 3.6969 (0.0330) C11 - 3.5099 (0.0341) C12 - 3.4170 (0.0259) C13 - 3.5154 (0.0133) C14 - 3.6674 (0.0119) C15 - 3.7577 (0.0236) C16 Rms deviation of fitted atoms = 0.0044 ############################## 0.7073 (0.0055) x + 12.3745 (0.0032) y - 3.9339 (0.0094) z = 4.3504 (0.0081) Angle to previous plane (with approximate e.s.d.) = 76.6 (5) * 0.0081 (0.0012) C21 * -0.0078 (0.0014) C22 * -0.0014 (0.0014) C23 * 0.0104 (0.0013) C24 * -0.0102 (0.0013) C25 * 0.0009 (0.0013) C26 - 3.4950 (0.0027) C21_$2 - 3.4790 (0.0027) C22_$2 - 3.4854 (0.0029) C23_$2 - 3.4972 (0.0026) C24_$2 - 3.4766 (0.0027) C25_$2 - 3.4878 (0.0027) C26_$2 Rms deviation of fitted atoms = 0.0075 ############################## 0.7073 (0.0055) x + 12.3745 (0.0032) y - 3.9339 (0.0094) z = 0.8636 (0.0091) Angle to previous plane = 0.0 * -0.0081 (0.0012) C21_$2 * 0.0078 (0.0014) C22_$2 * 0.0014 (0.0014) C23_$2 * -0.0104 (0.0013) C24_$2 * 0.0102 (0.0013) C25_$2 * -0.0009 (0.0013) C26_$2 3.4950 (0.0027) C21 3.4790 (0.0027) C22 3.4854 (0.0029) C23 3.4972 (0.0026) C24 3.4766 (0.0027) C25 3.4878 (0.0027) C26 Rms deviation of fitted atoms = 0.0075 ############################## 7.2402 (0.0033) x + 0.6161 (0.0367) y - 5.3065 (0.0230) z = 1.8163 (0.0025) Angle to previous plane (with approximate e.s.d.) = 79.41 (17) * -0.0107 (0.0054) N31 * 0.0181 (0.0057) C32 * -0.0141 (0.0051) C33 * 0.0041 (0.0031) C34 * 0.0037 (0.0035) C35 * -0.0006 (0.0028) C36 * -0.0006 (0.0031) C37 Rms deviation of fitted atoms = 0.0098 ############################## 6.9041 (0.0047) x + 2.8432 (0.0246) y - 6.6403 (0.0170) z = 1.8496 (0.0071) Angle to previous plane (with approximate e.s.d.) = 10.48 (16) * -0.0102 (0.0045) N41 * 0.0069 (0.0040) C42 * 0.0013 (0.0031) C43 * 0.0141 (0.0022) C44 * 0.0206 (0.0028) C45 * -0.0138 (0.0025) C46 * -0.0188 (0.0024) C47 Rms deviation of fitted atoms = 0.0138 ############################## 7.3288 (0.0076) x - 0.8049 (0.1338) y - 4.3665 (0.0997) z = 1.7875 (0.0097) Angle to previous plane (with approximate e.s.d.) = 17.1 (4) * 0.0329 (0.0171) N51 * 0.0033 (0.0068) C52 * -0.0176 (0.0126) C53 * 0.0327 (0.0122) C54 * 0.0679 (0.0166) C55 * -0.0865 (0.0175) C56 * -0.0327 (0.0108) C57 Rms deviation of fitted atoms = 0.0473 ############################## 7.0749 (0.0154) x + 1.4381 (0.1089) y - 6.2976 (0.0748) z = 2.0200 (0.0256) Angle to previous plane (with approximate e.s.d.) = 11.4 (5) * -0.0005 (0.0156) N61 * 0.0036 (0.0064) C62 * -0.0026 (0.0109) C63 * 0.0028 (0.0098) C64 * 0.0076 (0.0143) C65 * -0.0071 (0.0159) C66 * -0.0037 (0.0092) C67 Rms deviation of fitted atoms = 0.0046 ############################## 5.2262 (0.0062) x - 7.8164 (0.0114) y + 6.1170 (0.0118) z = 4.5879 (0.0076) Angle to previous plane (with approximate e.s.d.) = 61.7 (4) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 ############################## 7.2110 (0.0017) x - 0.2498 (0.0077) y - 5.4835 (0.0093) z = 1.6533 (0.0041) Angle to previous plane (with approximate e.s.d.) = 55.55 (7) * -0.0342 (0.0014) C11 * -0.0392 (0.0013) C12 * -0.0191 (0.0014) C13 * 0.0118 (0.0015) C14 * -0.0189 (0.0015) C15 * -0.0410 (0.0015) C16 * 0.0812 (0.0009) S1 * 0.0593 (0.0011) O14 Rms deviation of fitted atoms = 0.0438 ############################## 5.2262 (0.0062) x - 7.8164 (0.0114) y + 6.1170 (0.0118) z = 4.5879 (0.0076) Angle to previous plane (with approximate e.s.d.) = 55.55 (7) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 ############################## 0.6479 (0.0047) x + 12.3638 (0.0032) y - 3.7663 (0.0054) z = 4.4883 (0.0061) Angle to previous plane (with approximate e.s.d.) = 65.80 (6) * -0.0340 (0.0014) C21 * -0.0387 (0.0015) C22 * -0.0123 (0.0015) C23 * 0.0085 (0.0015) C24 * -0.0235 (0.0014) C25 * -0.0323 (0.0013) C26 * 0.0758 (0.0009) S1 * 0.0565 (0.0012) O24 Rms deviation of fitted atoms = 0.0409 |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.82943 (7) | 0.55391 (4) | 0.74918 (4) | 0.04926 (16) | |
O11 | 1.02967 (18) | 0.56344 (13) | 0.79019 (12) | 0.0697 (4) | |
O12 | 0.7643 (2) | 0.62654 (11) | 0.69430 (11) | 0.0656 (4) | |
O14 | 0.5387 (2) | 0.06276 (10) | 0.39318 (11) | 0.0601 (4) | |
O24 | 0.51420 (19) | 0.69229 (14) | 1.15436 (11) | 0.0621 (4) | |
C11 | 0.7301 (2) | 0.40695 (15) | 0.64627 (14) | 0.0420 (4) | |
C12 | 0.7484 (2) | 0.31507 (15) | 0.67547 (14) | 0.0464 (4) | |
C13 | 0.6825 (3) | 0.20075 (16) | 0.59032 (15) | 0.0497 (4) | |
C14 | 0.5977 (2) | 0.17650 (15) | 0.47434 (14) | 0.0444 (4) | |
C15 | 0.5755 (3) | 0.26910 (16) | 0.44650 (15) | 0.0534 (5) | |
C16 | 0.6415 (3) | 0.38335 (16) | 0.53204 (15) | 0.0514 (5) | |
C21 | 0.7369 (2) | 0.58675 (14) | 0.87023 (14) | 0.0428 (4) | |
C22 | 0.8532 (3) | 0.61383 (17) | 0.98039 (16) | 0.0531 (5) | |
C23 | 0.7809 (3) | 0.64904 (18) | 1.07650 (16) | 0.0562 (5) | |
C24 | 0.5921 (3) | 0.65669 (15) | 1.06364 (14) | 0.0459 (4) | |
C25 | 0.4759 (2) | 0.62635 (15) | 0.95253 (15) | 0.0478 (4) | |
C26 | 0.5482 (2) | 0.59275 (15) | 0.85702 (14) | 0.0473 (4) | |
N31 | 0.3703 (12) | 0.0257 (5) | 0.1680 (3) | 0.0516 (15) | 0.771 (5) |
C32 | 0.3394 (12) | 0.1049 (4) | 0.1295 (4) | 0.0742 (15) | 0.771 (5) |
C33 | 0.2534 (8) | 0.0812 (3) | 0.0156 (3) | 0.0671 (10) | 0.771 (5) |
C34 | 0.2030 (4) | −0.0317 (3) | −0.06983 (19) | 0.0483 (7) | 0.771 (5) |
C35 | 0.2377 (6) | −0.1174 (3) | −0.0323 (3) | 0.0672 (10) | 0.771 (5) |
C36 | 0.3215 (7) | −0.0854 (4) | 0.0865 (3) | 0.0622 (12) | 0.771 (5) |
C37 | 0.1152 (4) | −0.0581 (2) | −0.1918 (2) | 0.0549 (7) | 0.771 (5) |
N41 | −0.2424 (10) | −0.2480 (5) | −0.6352 (3) | 0.0597 (19) | 0.771 (5) |
C42 | −0.1767 (8) | −0.3280 (3) | −0.6038 (3) | 0.0580 (8) | 0.771 (5) |
C43 | −0.0798 (4) | −0.3025 (3) | −0.4912 (2) | 0.0515 (7) | 0.771 (5) |
C44 | −0.0404 (3) | −0.1887 (3) | −0.40347 (19) | 0.0453 (6) | 0.771 (5) |
C45 | −0.1048 (4) | −0.1049 (3) | −0.4355 (2) | 0.0596 (8) | 0.771 (5) |
C46 | −0.2070 (6) | −0.1383 (4) | −0.5509 (3) | 0.0648 (10) | 0.771 (5) |
C47 | 0.0600 (3) | −0.1622 (2) | −0.2827 (2) | 0.0504 (7) | 0.771 (5) |
N51 | 0.354 (4) | 0.0287 (18) | 0.1726 (9) | 0.063 (7)* | 0.229 (5) |
C52 | 0.297 (3) | −0.0852 (17) | 0.1039 (10) | 0.063 (2)* | 0.229 (5) |
C53 | 0.217 (2) | −0.1375 (10) | −0.0154 (9) | 0.063 (2)* | 0.229 (5) |
C54 | 0.1970 (17) | −0.0704 (8) | −0.0732 (6) | 0.041 (2)* | 0.229 (5) |
C55 | 0.257 (3) | 0.0503 (9) | −0.0029 (11) | 0.063 (2)* | 0.229 (5) |
C56 | 0.314 (4) | 0.0970 (14) | 0.1204 (11) | 0.063 (2)* | 0.229 (5) |
C57 | 0.1067 (12) | −0.1262 (7) | −0.1995 (6) | 0.053 (2)* | 0.229 (5) |
N61 | −0.231 (4) | −0.2414 (15) | −0.6349 (9) | 0.063 (7)* | 0.229 (5) |
C62 | −0.194 (2) | −0.1247 (12) | −0.5680 (9) | 0.063 (2)* | 0.229 (5) |
C63 | −0.1015 (17) | −0.0698 (8) | −0.4503 (8) | 0.063 (2)* | 0.229 (5) |
C64 | −0.0379 (13) | −0.1359 (7) | −0.3948 (6) | 0.041 (2)* | 0.229 (5) |
C65 | −0.073 (2) | −0.2563 (8) | −0.4629 (9) | 0.063 (2)* | 0.229 (5) |
C66 | −0.171 (3) | −0.3057 (10) | −0.5815 (10) | 0.063 (2)* | 0.229 (5) |
C67 | 0.0613 (11) | −0.0772 (7) | −0.2690 (6) | 0.053 (2)* | 0.229 (5) |
H14 | 0.4858 | 0.0595 | 0.3294 | 0.090* | |
H24 | 0.5952 | 0.7087 | 1.2156 | 0.093* | |
H12 | 0.8054 | 0.3307 | 0.7528 | 0.056* | |
H13 | 0.6946 | 0.1392 | 0.6103 | 0.060* | |
H15 | 0.5158 | 0.2539 | 0.3697 | 0.064* | |
H16 | 0.6262 | 0.4452 | 0.5128 | 0.062* | |
H22 | 0.9797 | 0.6083 | 0.9894 | 0.064* | |
H23 | 0.8593 | 0.6678 | 1.1505 | 0.067* | |
H25 | 0.3483 | 0.6288 | 0.9427 | 0.057* | |
H26 | 0.4698 | 0.5739 | 0.7830 | 0.057* | |
H32 | 0.3793 | 0.1837 | 0.1844 | 0.089* | 0.771 (5) |
H33 | 0.2298 | 0.1426 | −0.0030 | 0.080* | 0.771 (5) |
H35 | 0.2049 | −0.1966 | −0.0868 | 0.081* | 0.771 (5) |
H36 | 0.3437 | −0.1445 | 0.1091 | 0.075* | 0.771 (5) |
H37 | 0.0962 | 0.0061 | −0.2066 | 0.066* | 0.771 (5) |
H42 | −0.1981 | −0.4055 | −0.6617 | 0.070* | 0.771 (5) |
H43 | −0.0405 | −0.3624 | −0.4741 | 0.062* | 0.771 (5) |
H45 | −0.0797 | −0.0262 | −0.3799 | 0.072* | 0.771 (5) |
H46 | −0.2527 | −0.0808 | −0.5698 | 0.078* | 0.771 (5) |
H47 | 0.0875 | −0.2261 | −0.2693 | 0.060* | 0.771 (5) |
H52 | 0.3119 | −0.1347 | 0.1398 | 0.075* | 0.229 (5) |
H53 | 0.1771 | −0.2188 | −0.0566 | 0.075* | 0.229 (5) |
H55 | 0.2589 | 0.1004 | −0.0380 | 0.075* | 0.229 (5) |
H56 | 0.3248 | 0.1774 | 0.1664 | 0.075* | 0.229 (5) |
H57 | 0.0774 | −0.2081 | −0.2356 | 0.063* | 0.229 (5) |
H62 | −0.2345 | −0.0778 | −0.6037 | 0.075* | 0.229 (5) |
H63 | −0.0817 | 0.0118 | −0.4082 | 0.075* | 0.229 (5) |
H65 | −0.0317 | −0.3046 | −0.4292 | 0.075* | 0.229 (5) |
H66 | −0.1954 | −0.3873 | −0.6252 | 0.075* | 0.229 (5) |
H67 | 0.0958 | 0.0044 | −0.2347 | 0.063* | 0.229 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0547 (3) | 0.0437 (3) | 0.0353 (2) | −0.00104 (19) | 0.00831 (19) | 0.00829 (19) |
O11 | 0.0483 (8) | 0.0751 (10) | 0.0499 (8) | −0.0056 (7) | 0.0093 (6) | 0.0001 (7) |
O12 | 0.1037 (11) | 0.0448 (7) | 0.0469 (7) | 0.0051 (7) | 0.0206 (7) | 0.0207 (6) |
O14 | 0.0824 (10) | 0.0410 (7) | 0.0394 (7) | 0.0053 (6) | 0.0051 (7) | 0.0084 (6) |
O24 | 0.0586 (8) | 0.0849 (10) | 0.0385 (7) | 0.0176 (7) | 0.0118 (6) | 0.0240 (7) |
C11 | 0.0416 (9) | 0.0433 (9) | 0.0321 (8) | 0.0057 (7) | 0.0052 (7) | 0.0111 (7) |
C12 | 0.0510 (10) | 0.0521 (10) | 0.0305 (8) | 0.0067 (8) | 0.0049 (7) | 0.0167 (8) |
C13 | 0.0613 (11) | 0.0450 (10) | 0.0411 (10) | 0.0083 (8) | 0.0100 (8) | 0.0198 (8) |
C14 | 0.0477 (10) | 0.0409 (9) | 0.0351 (9) | 0.0062 (7) | 0.0082 (7) | 0.0102 (7) |
C15 | 0.0623 (12) | 0.0518 (11) | 0.0317 (9) | 0.0086 (9) | −0.0025 (8) | 0.0130 (8) |
C16 | 0.0636 (12) | 0.0430 (10) | 0.0387 (9) | 0.0114 (8) | 0.0017 (8) | 0.0160 (8) |
C21 | 0.0481 (10) | 0.0371 (9) | 0.0324 (8) | 0.0044 (7) | 0.0037 (7) | 0.0097 (7) |
C22 | 0.0473 (10) | 0.0655 (12) | 0.0413 (10) | 0.0153 (9) | 0.0055 (8) | 0.0216 (9) |
C23 | 0.0532 (11) | 0.0756 (13) | 0.0341 (9) | 0.0156 (10) | 0.0014 (8) | 0.0237 (9) |
C24 | 0.0521 (10) | 0.0472 (10) | 0.0355 (9) | 0.0088 (8) | 0.0074 (8) | 0.0182 (8) |
C25 | 0.0420 (10) | 0.0493 (10) | 0.0406 (10) | 0.0063 (8) | 0.0021 (8) | 0.0143 (8) |
C26 | 0.0497 (10) | 0.0454 (10) | 0.0308 (9) | 0.0028 (8) | −0.0037 (7) | 0.0104 (7) |
N31 | 0.060 (2) | 0.0457 (19) | 0.0315 (15) | 0.0075 (11) | 0.0033 (11) | 0.0064 (10) |
C32 | 0.102 (4) | 0.0460 (17) | 0.0426 (16) | −0.0030 (17) | −0.0095 (16) | 0.0073 (13) |
C33 | 0.097 (2) | 0.0458 (17) | 0.0417 (17) | 0.005 (2) | −0.0010 (17) | 0.0148 (14) |
C34 | 0.0502 (15) | 0.0453 (18) | 0.0395 (14) | 0.0034 (15) | 0.0030 (10) | 0.0152 (13) |
C35 | 0.092 (3) | 0.0415 (16) | 0.0365 (15) | 0.0006 (16) | −0.0017 (15) | −0.0009 (13) |
C36 | 0.080 (3) | 0.0492 (15) | 0.0393 (17) | 0.0136 (16) | 0.0031 (16) | 0.0091 (14) |
C37 | 0.0655 (17) | 0.0474 (15) | 0.0426 (14) | 0.0074 (12) | 0.0032 (12) | 0.0177 (12) |
N41 | 0.0457 (19) | 0.091 (3) | 0.0318 (15) | 0.0132 (13) | 0.0071 (9) | 0.0198 (13) |
C42 | 0.0534 (16) | 0.064 (2) | 0.0386 (16) | 0.0039 (17) | 0.0106 (15) | 0.0090 (14) |
C43 | 0.0507 (14) | 0.0563 (17) | 0.0413 (15) | 0.0052 (15) | 0.0090 (12) | 0.0189 (13) |
C44 | 0.0404 (13) | 0.0507 (18) | 0.0390 (13) | 0.0029 (13) | 0.0076 (10) | 0.0174 (13) |
C45 | 0.0661 (18) | 0.0535 (17) | 0.0421 (14) | 0.0088 (15) | 0.0036 (13) | 0.0116 (13) |
C46 | 0.065 (2) | 0.078 (2) | 0.0497 (19) | 0.0211 (16) | 0.0087 (15) | 0.0297 (16) |
C47 | 0.0544 (15) | 0.0504 (15) | 0.0387 (13) | 0.0044 (11) | 0.0055 (11) | 0.0173 (11) |
S1—O11 | 1.4397 (14) | C35—C36 | 1.399 (4) |
S1—O12 | 1.4409 (14) | C37—C47 | 1.308 (3) |
S1—C11 | 1.7585 (17) | N41—C42 | 1.335 (5) |
S1—C21 | 1.7516 (17) | N41—C46 | 1.323 (5) |
O14—C14 | 1.349 (2) | C42—C43 | 1.369 (4) |
O24—C24 | 1.344 (2) | C43—C44 | 1.373 (4) |
C11—C12 | 1.383 (2) | C44—C45 | 1.381 (4) |
C11—C16 | 1.379 (2) | C44—C47 | 1.464 (3) |
C12—C13 | 1.373 (2) | C45—C46 | 1.388 (4) |
C13—C14 | 1.390 (2) | N51—C52 | 1.317 (7) |
C14—C15 | 1.384 (3) | N51—C56 | 1.325 (6) |
C15—C16 | 1.374 (2) | C52—C53 | 1.368 (7) |
C21—C22 | 1.385 (2) | C53—C54 | 1.353 (6) |
C21—C26 | 1.381 (2) | C54—C55 | 1.391 (6) |
C22—C23 | 1.377 (3) | C54—C57 | 1.456 (5) |
C23—C24 | 1.386 (3) | C55—C56 | 1.402 (6) |
C24—C25 | 1.386 (2) | C57—C67 | 1.303 (5) |
C25—C26 | 1.371 (2) | N61—C62 | 1.337 (7) |
N31—C32 | 1.317 (4) | N61—C66 | 1.324 (7) |
N31—C36 | 1.322 (4) | C62—C63 | 1.369 (6) |
C32—C33 | 1.370 (4) | C63—C64 | 1.370 (5) |
C33—C34 | 1.354 (4) | C64—C65 | 1.378 (6) |
C34—C35 | 1.391 (4) | C64—C67 | 1.464 (5) |
C34—C37 | 1.457 (3) | C65—C66 | 1.389 (6) |
O11—S1—O12 | 117.84 (9) | C35—C34—C37 | 123.8 (2) |
O11—S1—C11 | 108.82 (8) | C34—C35—C36 | 120.6 (3) |
O11—S1—C21 | 107.58 (8) | N31—C36—C35 | 122.5 (3) |
O12—S1—C11 | 106.86 (8) | C34—C37—C47 | 127.1 (2) |
O12—S1—C21 | 107.90 (8) | C42—N41—C46 | 116.5 (2) |
C11—S1—C21 | 107.42 (8) | N41—C42—C43 | 123.8 (3) |
S1—C11—C12 | 121.72 (12) | C42—C43—C44 | 120.1 (3) |
S1—C11—C16 | 118.45 (13) | C43—C44—C45 | 116.5 (2) |
C12—C11—C16 | 119.72 (16) | C43—C44—C47 | 119.9 (2) |
C11—C12—C13 | 120.04 (15) | C45—C44—C47 | 123.6 (2) |
C12—C13—C14 | 120.37 (16) | C44—C45—C46 | 119.9 (3) |
O14—C14—C15 | 122.50 (15) | N41—C46—C45 | 123.1 (3) |
O14—C14—C13 | 118.30 (16) | C37—C47—C44 | 126.8 (2) |
C13—C14—C15 | 119.20 (16) | C52—N51—C56 | 115.2 (6) |
C14—C15—C16 | 120.19 (16) | N51—C52—C53 | 126.0 (8) |
C11—C16—C15 | 120.43 (17) | C52—C53—C54 | 119.7 (7) |
S1—C21—C22 | 120.63 (14) | C53—C54—C55 | 115.5 (5) |
S1—C21—C26 | 119.48 (13) | C53—C54—C57 | 119.4 (6) |
C22—C21—C26 | 119.77 (16) | C55—C54—C57 | 124.9 (6) |
C21—C22—C23 | 119.82 (17) | C54—C55—C56 | 120.5 (7) |
C22—C23—C24 | 120.44 (16) | N51—C56—C55 | 121.3 (8) |
O24—C24—C25 | 117.56 (16) | C54—C57—C67 | 128.9 (6) |
O24—C24—C23 | 123.18 (15) | C62—N61—C66 | 116.4 (6) |
C23—C24—C25 | 119.27 (16) | N61—C62—C63 | 124.3 (7) |
C24—C25—C26 | 120.32 (17) | C62—C63—C64 | 119.6 (6) |
C21—C26—C25 | 120.34 (16) | C63—C64—C65 | 116.8 (5) |
C32—N31—C36 | 115.6 (2) | C63—C64—C67 | 119.6 (5) |
N31—C32—C33 | 125.6 (3) | C65—C64—C67 | 123.6 (5) |
C32—C33—C34 | 120.0 (3) | C64—C65—C66 | 120.3 (6) |
C33—C34—C35 | 115.7 (2) | N61—C66—C65 | 122.6 (7) |
C33—C34—C37 | 120.6 (3) | C57—C67—C64 | 127.4 (6) |
O11—S1—C11—C16 | −117.56 (15) | C37—C34—C35—C36 | −179.6 (3) |
O12—S1—C11—C16 | 10.68 (17) | C32—N31—C36—C35 | −1.7 (8) |
C21—S1—C11—C16 | 126.25 (15) | C34—C35—C36—N31 | 0.3 (6) |
O11—S1—C11—C12 | 58.64 (17) | C33—C34—C37—C47 | 179.8 (4) |
O12—S1—C11—C12 | −173.12 (14) | C35—C34—C37—C47 | −1.4 (5) |
C21—S1—C11—C12 | −57.55 (16) | C46—N41—C42—C43 | 1.0 (9) |
C16—C11—C12—C13 | 1.5 (3) | N41—C42—C43—C44 | −1.8 (8) |
S1—C11—C12—C13 | −174.62 (14) | C42—C43—C44—C45 | 0.6 (5) |
C11—C12—C13—C14 | 0.3 (3) | C42—C43—C44—C47 | 178.8 (4) |
C12—C13—C14—O14 | 178.62 (16) | C43—C44—C45—C46 | 1.3 (4) |
C12—C13—C14—C15 | −1.9 (3) | C47—C44—C45—C46 | −176.8 (3) |
O14—C14—C15—C16 | −178.75 (18) | C42—N41—C46—C45 | 1.1 (7) |
C13—C14—C15—C16 | 1.8 (3) | C44—C45—C46—N41 | −2.2 (5) |
C14—C15—C16—C11 | −0.1 (3) | C34—C37—C47—C44 | 175.2 (3) |
C12—C11—C16—C15 | −1.6 (3) | C43—C44—C47—C37 | 176.4 (3) |
S1—C11—C16—C15 | 174.64 (15) | C45—C44—C47—C37 | −5.5 (4) |
O11—S1—C21—C26 | 175.13 (14) | C56—N51—C52—C53 | 6 (2) |
O12—S1—C21—C26 | 47.01 (16) | N51—C52—C53—C54 | 2.0 (15) |
C11—S1—C21—C26 | −67.86 (15) | C52—C53—C54—C55 | −2 (2) |
O11—S1—C21—C22 | −0.85 (18) | C52—C53—C54—C57 | −178.1 (12) |
O12—S1—C21—C22 | −128.96 (15) | C53—C54—C55—C56 | −7 (3) |
C11—S1—C21—C22 | 116.16 (16) | C57—C54—C55—C56 | 169.7 (17) |
C26—C21—C22—C23 | −1.4 (3) | C52—N51—C56—C55 | −14 (3) |
S1—C21—C22—C23 | 174.56 (15) | C54—C55—C56—N51 | 15 (4) |
C21—C22—C23—C24 | 0.5 (3) | C53—C54—C57—C67 | 174.3 (12) |
C22—C23—C24—O24 | −178.89 (18) | C55—C54—C57—C67 | −2 (2) |
C22—C23—C24—C25 | 1.2 (3) | C66—N61—C62—C63 | 0 (2) |
O24—C24—C25—C26 | 178.04 (17) | N61—C62—C63—C64 | 0.8 (13) |
C23—C24—C25—C26 | −2.1 (3) | C62—C63—C64—C65 | −0.3 (18) |
C24—C25—C26—C21 | 1.2 (3) | C62—C63—C64—C67 | 180.0 (10) |
C22—C21—C26—C25 | 0.6 (3) | C63—C64—C65—C66 | −1 (2) |
S1—C21—C26—C25 | −175.45 (14) | C67—C64—C65—C66 | 179.0 (15) |
C36—N31—C32—C33 | 3.6 (12) | C62—N61—C66—C65 | −1 (3) |
N31—C32—C33—C34 | −4.2 (12) | C64—C65—C66—N61 | 1 (3) |
C32—C33—C34—C35 | 2.4 (8) | C54—C57—C67—C64 | −176.8 (11) |
C32—C33—C34—C37 | −178.7 (6) | C63—C64—C67—C57 | 169.4 (10) |
C33—C34—C35—C36 | −0.7 (6) | C65—C64—C67—C57 | −10.2 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N31 | 0.82 | 1.93 | 2.743 (4) | 171 |
O14—H14···N51 | 0.82 | 1.92 | 2.730 (7) | 172 |
O24—H24···N41i | 0.82 | 1.87 | 2.688 (5) | 173 |
O24—H24···N61i | 0.82 | 1.90 | 2.714 (7) | 174 |
C16—H16···O12 | 0.93 | 2.44 | 2.848 (2) | 107 |
C22—H22···O11 | 0.93 | 2.52 | 2.898 (2) | 104 |
C25—H25···O11ii | 0.93 | 2.55 | 3.344 (2) | 144 |
Symmetry codes: (i) x+1, y+1, z+2; (ii) x−1, y, z. |
C12H10O4S·C12H12N2 | F(000) = 456 |
Mr = 434.50 | ? #Insert any comments here. |
Triclinic, P1 | Dx = 1.329 Mg m−3 |
a = 7.7599 (9) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 12.4866 (16) Å | Cell parameters from 25 reflections |
c = 12.914 (2) Å | θ = 9.8–22.5° |
α = 114.003 (14)° | µ = 0.18 mm−1 |
β = 104.694 (14)° | T = 294 K |
γ = 93.690 (13)° | Plate, colourless |
V = 1085.7 (3) Å3 | 0.42 × 0.42 × 0.32 mm |
Z = 2 |
Enraf-Nonius CAD-4 diffractometer | 3905 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.000 |
Graphite monochromator | θmax = 27.4°, θmin = 2.8° |
θ/2θ scans | h = −10→9 |
Absorption correction: gaussian ABSO in NRCVAX (Gabe et al., 1989) | k = 0→16 |
Tmin = 0.934, Tmax = 0.951 | l = −16→15 |
4973 measured reflections | 3 standard reflections every 120 min |
4973 independent reflections | intensity decay: no decay, variation 0.7% |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0602P)2 + 0.2544P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
4973 reflections | Δρmax = 0.43 e Å−3 |
283 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.015 (2) |
C12H10O4S·C12H12N2 | γ = 93.690 (13)° |
Mr = 434.50 | V = 1085.7 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.7599 (9) Å | Mo Kα radiation |
b = 12.4866 (16) Å | µ = 0.18 mm−1 |
c = 12.914 (2) Å | T = 294 K |
α = 114.003 (14)° | 0.42 × 0.42 × 0.32 mm |
β = 104.694 (14)° |
Enraf-Nonius CAD-4 diffractometer | 3905 reflections with I > 2σ(I) |
Absorption correction: gaussian ABSO in NRCVAX (Gabe et al., 1989) | Rint = 0.000 |
Tmin = 0.934, Tmax = 0.951 | 3 standard reflections every 120 min |
4973 measured reflections | intensity decay: no decay, variation 0.7% |
4973 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.43 e Å−3 |
4973 reflections | Δρmin = −0.32 e Å−3 |
283 parameters |
Experimental. ? #Insert any special details here. |
Geometry. Mean-plane data ex last SHELXL run. Equivalent position indicated by $1 is: -x, -y, -z Equivalent position indicated by $2 is: 1 - x, 1 - y, 2 - z Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.4936 (0.0024) x + 0.4452 (0.0097) y - 6.4003 (0.0090) z = 1.4297 (0.0052) * 0.0143 (0.0012) C11 * -0.0090 (0.0012) C12 * -0.0070 (0.0013) C13 * 0.0178 (0.0012) C14 * -0.0127 (0.0013) C15 * -0.0034 (0.0013) C16 - 3.5241 (0.0020) N41_$1 - 3.8413 (0.0025) C42_$1 - 4.0056 (0.0029) C43_$1 - 3.8641 (0.0030) C44_$1 - 3.5478 (0.0033) C45_$1 - 3.3698 (0.0029) C46_$1 Rms deviation of fitted atoms = 0.0117 - 6.9555 (0.0034) x - 3.1748 (0.0121) y + 8.1781 (0.0082) z = 2.6502 (0.0046) Angle to previous plane (with approximate e.s.d.) = 13.63 (0.07) * 0.0013 (0.0014) N41_$1 * 0.0069 (0.0014) C42_$1 * -0.0072 (0.0014) C43_$1 * -0.0002 (0.0014) C44_$1 * 0.0081 (0.0017) C45_$1 * -0.0089 (0.0017) C46_$1 - 3.6553 (0.0029) C11 - 3.3077 (0.0032) C12 - 3.1802 (0.0033) C13 - 3.3989 (0.0027) C14 - 3.6925 (0.0023) C15 - 3.8300 (0.0026) C16 Rms deviation of fitted atoms = 0.0064 0.9838 (0.0053) x + 11.9886 (0.0039) y - 3.4143 (0.0089) z = 4.7874 (0.0075) Angle to previous plane (with approximate e.s.d.) = 69.38 (0.07) * 0.0045 (0.0011) C21 * -0.0055 (0.0013) C22 * 0.0007 (0.0013) C23 * 0.0050 (0.0012) C24 * -0.0061 (0.0011) C25 * 0.0013 (0.0011) C26 - 3.4355 (0.0027) C21_$2 - 3.4255 (0.0026) C22_$2 - 3.4317 (0.0028) C23_$2 - 3.4360 (0.0026) C24_$2 - 3.4249 (0.0026) C25_$2 - 3.4323 (0.0026) C26_$2 Rms deviation of fitted atoms = 0.0044 0.9838 (0.0053) x + 11.9886 (0.0039) y - 3.4143 (0.0089) z = 1.3564 (0.0085) Angle to previous plane (with approximate e.s.d.) = 0.00 (0.06) * -0.0045 (0.0011) C21_$2 * 0.0055 (0.0013) C22_$2 * -0.0007 (0.0013) C23_$2 * -0.0050 (0.0012) C24_$2 * 0.0061 (0.0011) C25_$2 * -0.0013 (0.0011) C26_$2 3.4355 (0.0027) C21 3.4255 (0.0026) C22 3.4317 (0.0028) C23 3.4360 (0.0026) C24 3.4249 (0.0026) C25 3.4323 (0.0026) C26 Rms deviation of fitted atoms = 0.0044 7.1628 (0.0026) x - 2.3267 (0.0111) y - 6.4033 (0.0073) z = 1.7542 (0.0010) Angle to previous plane (with approximate e.s.d.) = 85.34 (0.07) * -0.0335 (0.0013) N31 * -0.0009 (0.0014) C32 * 0.0281 (0.0016) C33 * 0.0148 (0.0017) C34 * 0.0279 (0.0016) C35 * 0.0001 (0.0014) C36 * -0.0364 (0.0012) C37 Rms deviation of fitted atoms = 0.0246 6.9514 (0.0031) x + 3.1777 (0.0120) y - 8.1923 (0.0063) z = 2.6580 (0.0034) Angle to previous plane (with approximate e.s.d.) = 25.62 (0.06) * 0.0028 (0.0015) N41 * 0.0074 (0.0014) C42 * -0.0086 (0.0016) C43 * -0.0027 (0.0017) C44 * 0.0066 (0.0019) C45 * -0.0084 (0.0017) C46 * 0.0029 (0.0013) C47 Rms deviation of fitted atoms = 0.0062 5.1493 (0.0066) x - 7.7839 (0.0106) y + 6.2915 (0.0109) z = 4.6645 (0.0073) Angle to previous plane (with approximate e.s.d.) = 74.69 (0.06) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 7.4831 (0.0024) x + 0.3349 (0.0075) y - 6.4452 (0.0088) z = 1.3918 (0.0041) Angle to previous plane (with approximate e.s.d.) = 61.91 (0.06) * -0.0295 (0.0013) C11 * -0.0441 (0.0013) C12 * -0.0248 (0.0014) C13 * 0.0089 (0.0015) C14 * -0.0304 (0.0014) C15 * -0.0384 (0.0014) C16 * 0.0859 (0.0009) S1 * 0.0723 (0.0011) O14 Rms deviation of fitted atoms = 0.0481 5.1493 (0.0066) x - 7.7839 (0.0106) y + 6.2915 (0.0109) z = 4.6645 (0.0073) Angle to previous plane (with approximate e.s.d.) = 61.91 (0.06) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 0.9343 (0.0045) x + 11.9817 (0.0039) y - 3.2961 (0.0054) z = 4.8780 (0.0059) Angle to previous plane (with approximate e.s.d.) = 67.46 (0.06) * -0.0232 (0.0013) C21 * -0.0254 (0.0014) C22 * -0.0048 (0.0014) C23 * 0.0062 (0.0014) C24 * -0.0127 (0.0012) C25 * -0.0197 (0.0012) C26 * 0.0472 (0.0008) S1 * 0.0323 (0.0011) O24 Rms deviation of fitted atoms = 0.0252 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.82235 (6) | 0.55444 (4) | 0.75430 (4) | 0.04529 (14) | |
O11 | 1.01380 (17) | 0.56195 (12) | 0.80197 (12) | 0.0637 (4) | |
O12 | 0.7644 (2) | 0.62870 (11) | 0.69620 (12) | 0.0644 (4) | |
O14 | 0.5356 (2) | 0.05715 (11) | 0.39760 (11) | 0.0590 (4) | |
O24 | 0.50738 (18) | 0.68579 (13) | 1.14705 (11) | 0.0567 (3) | |
C11 | 0.7243 (2) | 0.40583 (14) | 0.65068 (13) | 0.0391 (3) | |
C12 | 0.7524 (2) | 0.31208 (15) | 0.68072 (14) | 0.0447 (4) | |
C13 | 0.6869 (3) | 0.19626 (15) | 0.59558 (15) | 0.0491 (4) | |
C14 | 0.5920 (2) | 0.17269 (14) | 0.47903 (14) | 0.0429 (4) | |
C15 | 0.5584 (2) | 0.26648 (16) | 0.45090 (14) | 0.0491 (4) | |
C16 | 0.6256 (3) | 0.38222 (15) | 0.53616 (14) | 0.0481 (4) | |
C21 | 0.7297 (2) | 0.58808 (13) | 0.87172 (13) | 0.0388 (3) | |
C22 | 0.8382 (2) | 0.61042 (16) | 0.98433 (15) | 0.0480 (4) | |
C23 | 0.7659 (2) | 0.64345 (17) | 1.07763 (15) | 0.0518 (4) | |
C24 | 0.5848 (2) | 0.65341 (14) | 1.05917 (14) | 0.0419 (4) | |
C25 | 0.4755 (2) | 0.62909 (14) | 0.94553 (14) | 0.0437 (4) | |
C26 | 0.5482 (2) | 0.59739 (14) | 0.85305 (14) | 0.0429 (4) | |
N31 | 0.3942 (2) | 0.01783 (13) | 0.16574 (12) | 0.0483 (3) | |
C32 | 0.3800 (3) | 0.09352 (16) | 0.11731 (16) | 0.0537 (4) | |
C33 | 0.2733 (3) | 0.06495 (18) | 0.00375 (16) | 0.0560 (5) | |
C34 | 0.1713 (3) | −0.04915 (17) | −0.06678 (15) | 0.0523 (4) | |
C35 | 0.1904 (3) | −0.12917 (16) | −0.01837 (16) | 0.0568 (5) | |
C36 | 0.3010 (3) | −0.09299 (16) | 0.09651 (16) | 0.0522 (4) | |
C37 | 0.0424 (3) | −0.0851 (2) | −0.18997 (17) | 0.0691 (6) | |
N41 | −0.2507 (2) | −0.26148 (17) | −0.63894 (13) | 0.0607 (4) | |
C42 | −0.1746 (3) | −0.3384 (2) | −0.60482 (17) | 0.0618 (5) | |
C43 | −0.0589 (3) | −0.30801 (19) | −0.49284 (16) | 0.0582 (5) | |
C44 | −0.0141 (2) | −0.19092 (19) | −0.41014 (15) | 0.0549 (5) | |
C45 | −0.0911 (3) | −0.1100 (2) | −0.44520 (19) | 0.0703 (6) | |
C46 | −0.2100 (3) | −0.1488 (2) | −0.55931 (19) | 0.0703 (6) | |
C47 | 0.1154 (3) | −0.1543 (2) | −0.28671 (17) | 0.0700 (6) | |
H14 | 0.4981 | 0.0538 | 0.3308 | 0.089* | |
H24 | 0.5830 | 0.6972 | 1.2096 | 0.085* | |
H12 | 0.8156 | 0.3277 | 0.7585 | 0.054* | |
H13 | 0.7058 | 0.1335 | 0.6157 | 0.059* | |
H15 | 0.4902 | 0.2513 | 0.3742 | 0.059* | |
H16 | 0.6043 | 0.4450 | 0.5165 | 0.058* | |
H22 | 0.9595 | 0.6032 | 0.9970 | 0.058* | |
H23 | 0.8390 | 0.6591 | 1.1533 | 0.062* | |
H25 | 0.3534 | 0.6343 | 0.9322 | 0.052* | |
H26 | 0.4753 | 0.5821 | 0.7774 | 0.052* | |
H32 | 0.4466 | 0.1708 | 0.1631 | 0.064* | |
H33 | 0.2694 | 0.1218 | −0.0256 | 0.067* | |
H35 | 0.1287 | −0.2078 | −0.0632 | 0.068* | |
H36 | 0.3110 | −0.1488 | 0.1272 | 0.063* | |
H37A | −0.0695 | −0.1323 | −0.1991 | 0.083* | |
H37B | 0.0133 | −0.0137 | −0.1974 | 0.083* | |
H42 | −0.2012 | −0.4182 | −0.6601 | 0.074* | |
H43 | −0.0115 | −0.3664 | −0.4735 | 0.070* | |
H45 | −0.0634 | −0.0293 | −0.3924 | 0.084* | |
H46 | −0.2631 | −0.0929 | −0.5804 | 0.084* | |
H47A | 0.1451 | −0.2256 | −0.2790 | 0.084* | |
H47B | 0.2270 | −0.1070 | −0.2779 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0500 (3) | 0.0392 (2) | 0.0382 (2) | 0.00062 (16) | 0.01294 (17) | 0.01030 (16) |
O11 | 0.0438 (7) | 0.0654 (8) | 0.0552 (8) | −0.0044 (6) | 0.0137 (6) | 0.0038 (6) |
O12 | 0.0994 (11) | 0.0450 (7) | 0.0531 (8) | 0.0071 (7) | 0.0283 (8) | 0.0236 (6) |
O14 | 0.0811 (10) | 0.0418 (6) | 0.0369 (6) | −0.0001 (6) | 0.0067 (6) | 0.0091 (5) |
O24 | 0.0539 (8) | 0.0759 (9) | 0.0389 (6) | 0.0187 (7) | 0.0144 (6) | 0.0227 (6) |
C11 | 0.0393 (8) | 0.0390 (8) | 0.0324 (7) | 0.0059 (6) | 0.0096 (6) | 0.0103 (6) |
C12 | 0.0498 (9) | 0.0473 (9) | 0.0306 (7) | 0.0039 (7) | 0.0054 (7) | 0.0157 (7) |
C13 | 0.0635 (11) | 0.0426 (9) | 0.0391 (8) | 0.0064 (8) | 0.0107 (8) | 0.0193 (7) |
C14 | 0.0445 (9) | 0.0415 (8) | 0.0342 (8) | 0.0035 (7) | 0.0099 (6) | 0.0105 (6) |
C15 | 0.0533 (10) | 0.0526 (9) | 0.0302 (7) | 0.0161 (8) | 0.0026 (7) | 0.0125 (7) |
C16 | 0.0588 (10) | 0.0440 (9) | 0.0372 (8) | 0.0189 (8) | 0.0088 (7) | 0.0159 (7) |
C21 | 0.0434 (8) | 0.0322 (7) | 0.0337 (7) | 0.0044 (6) | 0.0076 (6) | 0.0104 (6) |
C22 | 0.0405 (9) | 0.0599 (10) | 0.0420 (8) | 0.0153 (8) | 0.0069 (7) | 0.0233 (8) |
C23 | 0.0477 (10) | 0.0686 (12) | 0.0352 (8) | 0.0146 (8) | 0.0040 (7) | 0.0237 (8) |
C24 | 0.0451 (9) | 0.0412 (8) | 0.0367 (8) | 0.0087 (7) | 0.0097 (7) | 0.0160 (7) |
C25 | 0.0372 (8) | 0.0449 (9) | 0.0394 (8) | 0.0073 (7) | 0.0039 (6) | 0.0137 (7) |
C26 | 0.0434 (9) | 0.0404 (8) | 0.0314 (7) | 0.0031 (6) | −0.0002 (6) | 0.0103 (6) |
N31 | 0.0497 (8) | 0.0463 (8) | 0.0347 (7) | 0.0046 (6) | 0.0056 (6) | 0.0091 (6) |
C32 | 0.0593 (11) | 0.0422 (9) | 0.0441 (9) | −0.0019 (8) | 0.0073 (8) | 0.0108 (7) |
C33 | 0.0687 (12) | 0.0537 (10) | 0.0436 (9) | 0.0106 (9) | 0.0139 (8) | 0.0214 (8) |
C34 | 0.0524 (10) | 0.0563 (10) | 0.0341 (8) | 0.0165 (8) | 0.0091 (7) | 0.0080 (8) |
C35 | 0.0596 (11) | 0.0406 (9) | 0.0450 (9) | 0.0019 (8) | 0.0024 (8) | 0.0036 (7) |
C36 | 0.0599 (11) | 0.0423 (9) | 0.0450 (9) | 0.0086 (8) | 0.0100 (8) | 0.0138 (7) |
C37 | 0.0633 (13) | 0.0865 (15) | 0.0401 (10) | 0.0262 (11) | 0.0071 (9) | 0.0144 (10) |
N41 | 0.0490 (9) | 0.0903 (13) | 0.0355 (7) | 0.0141 (8) | 0.0103 (6) | 0.0222 (8) |
C42 | 0.0556 (11) | 0.0707 (13) | 0.0414 (10) | 0.0051 (10) | 0.0104 (8) | 0.0114 (9) |
C43 | 0.0549 (11) | 0.0718 (13) | 0.0449 (10) | 0.0135 (9) | 0.0130 (8) | 0.0239 (9) |
C44 | 0.0418 (9) | 0.0790 (13) | 0.0366 (8) | 0.0129 (9) | 0.0105 (7) | 0.0190 (9) |
C45 | 0.0744 (14) | 0.0667 (13) | 0.0475 (11) | 0.0143 (11) | 0.0075 (10) | 0.0102 (10) |
C46 | 0.0733 (14) | 0.0842 (16) | 0.0515 (11) | 0.0258 (12) | 0.0120 (10) | 0.0306 (11) |
C47 | 0.0533 (12) | 0.1002 (17) | 0.0385 (9) | 0.0218 (11) | 0.0068 (8) | 0.0165 (10) |
S1—O11 | 1.4373 (14) | C25—C26 | 1.374 (2) |
S1—O12 | 1.4399 (14) | N31—C32 | 1.325 (2) |
S1—C11 | 1.7591 (16) | N31—C36 | 1.332 (2) |
S1—C21 | 1.7510 (17) | C32—C33 | 1.373 (3) |
O14—C14 | 1.3528 (19) | C33—C34 | 1.385 (3) |
O24—C24 | 1.347 (2) | C34—C35 | 1.375 (3) |
C11—C12 | 1.388 (2) | C34—C37 | 1.512 (2) |
C11—C16 | 1.379 (2) | C35—C36 | 1.378 (3) |
C12—C13 | 1.374 (2) | C37—C47 | 1.474 (3) |
C13—C14 | 1.394 (2) | N41—C42 | 1.323 (3) |
C14—C15 | 1.382 (2) | N41—C46 | 1.318 (3) |
C15—C16 | 1.375 (2) | C42—C43 | 1.376 (3) |
C21—C22 | 1.386 (2) | C43—C44 | 1.369 (3) |
C21—C26 | 1.388 (2) | C44—C45 | 1.377 (3) |
C22—C23 | 1.381 (2) | C44—C47 | 1.515 (2) |
C23—C24 | 1.387 (2) | C45—C46 | 1.389 (3) |
C24—C25 | 1.392 (2) | ||
O11—S1—O12 | 118.23 (9) | O24—C24—C25 | 117.50 (15) |
O11—S1—C11 | 108.62 (8) | C23—C24—C25 | 119.60 (15) |
O12—S1—C11 | 107.03 (8) | C24—C25—C26 | 119.87 (15) |
O11—S1—C21 | 107.41 (8) | C21—C26—C25 | 120.49 (14) |
O12—S1—C21 | 107.97 (8) | C32—N31—C36 | 116.34 (15) |
C11—S1—C21 | 107.10 (7) | N31—C32—C33 | 124.09 (17) |
S1—C11—C12 | 121.06 (12) | C32—C33—C34 | 119.55 (18) |
S1—C11—C16 | 119.12 (13) | C33—C34—C35 | 116.54 (16) |
C12—C11—C16 | 119.74 (15) | C33—C34—C37 | 122.54 (19) |
C11—C12—C13 | 119.97 (15) | C35—C34—C37 | 120.91 (18) |
C12—C13—C14 | 120.09 (16) | C34—C35—C36 | 120.09 (17) |
O14—C14—C13 | 117.83 (15) | N31—C36—C35 | 123.32 (17) |
O14—C14—C15 | 122.58 (15) | C34—C37—C47 | 113.61 (17) |
C13—C14—C15 | 119.58 (15) | C42—N41—C46 | 116.77 (17) |
C14—C15—C16 | 120.05 (15) | N41—C42—C43 | 124.2 (2) |
C11—C16—C15 | 120.47 (16) | C42—C43—C44 | 119.3 (2) |
S1—C21—C22 | 120.42 (13) | C43—C44—C45 | 116.85 (17) |
S1—C21—C26 | 119.75 (12) | C43—C44—C47 | 120.6 (2) |
C22—C21—C26 | 119.78 (15) | C45—C44—C47 | 122.6 (2) |
C21—C22—C23 | 119.83 (16) | C44—C45—C46 | 120.1 (2) |
C22—C23—C24 | 120.42 (15) | N41—C46—C45 | 122.7 (2) |
O24—C24—C23 | 122.90 (15) | C37—C47—C44 | 113.62 (17) |
O11—S1—C11—C16 | −124.45 (15) | O24—C24—C25—C26 | 179.04 (15) |
O12—S1—C11—C16 | 4.25 (16) | C23—C24—C25—C26 | −1.1 (3) |
C21—S1—C11—C16 | 119.84 (14) | C24—C25—C26—C21 | 0.7 (2) |
O11—S1—C11—C12 | 52.30 (16) | C22—C21—C26—C25 | 0.3 (2) |
O12—S1—C11—C12 | −179.00 (14) | S1—C21—C26—C25 | −177.01 (12) |
C21—S1—C11—C12 | −63.41 (15) | C36—N31—C32—C33 | 1.8 (3) |
C16—C11—C12—C13 | 2.0 (3) | N31—C32—C33—C34 | 0.4 (3) |
S1—C11—C12—C13 | −174.69 (14) | C32—C33—C34—C35 | −2.6 (3) |
C11—C12—C13—C14 | 0.0 (3) | C32—C33—C34—C37 | 176.35 (19) |
C12—C13—C14—O14 | 177.82 (16) | C33—C34—C35—C36 | 2.5 (3) |
C12—C13—C14—C15 | −2.5 (3) | C37—C34—C35—C36 | −176.42 (18) |
O14—C14—C15—C16 | −177.29 (17) | C32—N31—C36—C35 | −1.9 (3) |
C13—C14—C15—C16 | 3.1 (3) | C34—C35—C36—N31 | −0.3 (3) |
C14—C15—C16—C11 | −1.1 (3) | C35—C34—C37—C47 | −79.2 (3) |
C12—C11—C16—C15 | −1.5 (3) | C33—C34—C37—C47 | 101.9 (3) |
S1—C11—C16—C15 | 175.29 (14) | C46—N41—C42—C43 | 0.5 (3) |
O11—S1—C21—C22 | −2.71 (17) | N41—C42—C43—C44 | −1.4 (3) |
O12—S1—C21—C22 | −131.23 (14) | C42—C43—C44—C45 | 0.6 (3) |
C11—S1—C21—C22 | 113.81 (14) | C42—C43—C44—C47 | −178.99 (19) |
O11—S1—C21—C26 | 174.56 (13) | C43—C44—C45—C46 | 0.9 (3) |
O12—S1—C21—C26 | 46.04 (15) | C47—C44—C45—C46 | −179.6 (2) |
C11—S1—C21—C26 | −68.92 (14) | C42—N41—C46—C45 | 1.1 (3) |
C26—C21—C22—C23 | −0.9 (3) | C44—C45—C46—N41 | −1.8 (4) |
S1—C21—C22—C23 | 176.34 (14) | C34—C37—C47—C44 | 179.7 (2) |
C21—C22—C23—C24 | 0.6 (3) | C43—C44—C47—C37 | −126.6 (2) |
C22—C23—C24—O24 | −179.70 (17) | C45—C44—C47—C37 | 53.9 (3) |
C22—C23—C24—C25 | 0.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N31 | 0.82 | 1.92 | 2.735 (2) | 170 |
O24—H24···N41i | 0.82 | 1.89 | 2.706 (2) | 174 |
C16—H16···O12 | 0.93 | 2.46 | 2.859 (2) | 106 |
C22—H22···O11 | 0.93 | 2.51 | 2.889 (2) | 105 |
C46—H46···O14ii | 0.93 | 2.57 | 3.476 (3) | 164 |
Symmetry codes: (i) x+1, y+1, z+2; (ii) x−1, y, z−1. |
C12H10O4S·C13H14N2 | F(000) = 944 |
Mr = 448.52 | ? #Insert any comments here. |
Monoclinic, P21/c | Dx = 1.317 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.7107 Å |
a = 10.0292 (10) Å | Cell parameters from 10602 reflections |
b = 15.579 (2) Å | θ = 2.6–30.3° |
c = 15.0208 (10) Å | µ = 0.18 mm−1 |
β = 105.4699 (10)° | T = 150 K |
V = 2261.9 (4) Å3 | Block cut from larger piece, colourless |
Z = 4 | 0.30 × 0.30 × 0.30 mm |
Enraf-Nonius KappaCCD diffractometer | 3828 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.031 |
Graphite monochromator | θmax = 30.2°, θmin = 2.6° |
ω scans | h = −12→12 |
10602 measured reflections | k = −19→19 |
5465 independent reflections | l = −19→19 |
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)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.062P)2 + 0.2027P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
5465 reflections | Δρmax = 0.27 e Å−3 |
292 parameters | Δρmin = −0.36 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0066 (14) |
C12H10O4S·C13H14N2 | V = 2261.9 (4) Å3 |
Mr = 448.52 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.0292 (10) Å | µ = 0.18 mm−1 |
b = 15.579 (2) Å | T = 150 K |
c = 15.0208 (10) Å | 0.30 × 0.30 × 0.30 mm |
β = 105.4699 (10)° |
Enraf-Nonius KappaCCD diffractometer | 3828 reflections with I > 2σ(I) |
10602 measured reflections | Rint = 0.031 |
5465 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.27 e Å−3 |
5465 reflections | Δρmin = −0.36 e Å−3 |
292 parameters |
Experimental. ? #Insert any special details here. |
Geometry. Mean-plane calculations from final SHELXL run Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.8903 (0.0052) x - 8.3115 (0.0145) y - 9.8944 (0.0138) z = 0.0933 (0.0019) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O12 Rms deviation of fitted atoms = 0.0000 7.2284 (0.0052) x + 8.0318 (0.0126) y + 3.8210 (0.0131) z = 2.6926 (0.0005) Angle to previous plane (with approximate e.s.d.) = 89.51 (0.06) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 - 3.9991 (0.0054) x - 2.6996 (0.0065) y + 14.6344 (0.0029) z = 0.1858 (0.0020) Angle to previous plane (with approximate e.s.d.) = 87.67 (0.06) * 0.0234 (0.0013) C11 * -0.0001 (0.0012) C12 * -0.0081 (0.0013) C13 * -0.0051 (0.0015) C14 * -0.0148 (0.0013) C15 * 0.0062 (0.0012) C16 * -0.0108 (0.0007) S1 * 0.0094 (0.0011) O14 Rms deviation of fitted atoms = 0.0117 7.2284 (0.0052) x + 8.0318 (0.0126) y + 3.8210 (0.0131) z = 2.6926 (0.0005) Angle to previous plane (with approximate e.s.d.) = 87.67 (0.06) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 - 2.6440 (0.0054) x + 14.9139 (0.0034) y - 0.6618 (0.0039) z = 0.4068 (0.0019) Angle to previous plane (with approximate e.s.d.) = 75.61 (0.05) * -0.0257 (0.0012) C21 * -0.0302 (0.0012) C22 * -0.0132 (0.0012) C23 * 0.0071 (0.0012) C24 * -0.0165 (0.0011) C25 * -0.0244 (0.0011) C26 * 0.0586 (0.0007) S1 * 0.0442 (0.0009) O24 Rms deviation of fitted atoms = 0.0317 - 3.2131 (0.0059) x + 9.2026 (0.0086) y + 12.0044 (0.0063) z = 4.5255 (0.0042) Angle to previous plane (with approximate e.s.d.) = 55.80 (0.04) * 0.0041 (0.0010) N31 * -0.0016 (0.0012) C32 * -0.0038 (0.0012) C33 * 0.0067 (0.0010) C34 * -0.0043 (0.0011) C35 * -0.0011 (0.0011) C36 0.0896 (0.0026) C51 - 0.4867 (0.0029) C52 - 0.3405 (0.0037) C53 Rms deviation of fitted atoms = 0.0040 1.1888 (0.0066) x + 0.2105 (0.0107) y - 14.8481 (0.0024) z = 2.0016 (0.0089) Angle to previous plane (with approximate e.s.d.) = 40.07 (0.05) * -0.0034 (0.0011) N41 * -0.0019 (0.0012) C42 * 0.0068 (0.0011) C43 * -0.0066 (0.0011) C44 * 0.0016 (0.0012) C45 * 0.0035 (0.0012) C46 - 0.6781 (0.0037) C51 - 0.5929 (0.0029) C52 - 0.0347 (0.0026) C53 Rms deviation of fitted atoms = 0.0045 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.23814 (4) | 0.07748 (3) | 0.09133 (3) | 0.03407 (12) | |
O11 | 0.14797 (12) | 0.00489 (8) | 0.08950 (9) | 0.0437 (3) | |
O12 | 0.35940 (12) | 0.08684 (8) | 0.16790 (8) | 0.0439 (3) | |
O14 | −0.08787 (12) | 0.39407 (8) | 0.06202 (10) | 0.0508 (3) | |
O24 | 0.40552 (11) | 0.09085 (7) | −0.25431 (7) | 0.0353 (3) | |
C11 | 0.13838 (15) | 0.17092 (10) | 0.08364 (10) | 0.0304 (3) | |
C12 | −0.00415 (15) | 0.16806 (10) | 0.04256 (11) | 0.0356 (4) | |
C13 | −0.08130 (16) | 0.24228 (11) | 0.03462 (12) | 0.0376 (4) | |
C14 | −0.01805 (15) | 0.31998 (10) | 0.06644 (11) | 0.0357 (4) | |
C15 | 0.12475 (15) | 0.32275 (11) | 0.10531 (12) | 0.0368 (4) | |
C16 | 0.20157 (15) | 0.24850 (11) | 0.11404 (10) | 0.0340 (3) | |
C21 | 0.29251 (14) | 0.07695 (9) | −0.01041 (10) | 0.0285 (3) | |
C22 | 0.19855 (15) | 0.05628 (10) | −0.09397 (11) | 0.0337 (3) | |
C23 | 0.23872 (15) | 0.06097 (10) | −0.17438 (11) | 0.0327 (3) | |
C24 | 0.37310 (15) | 0.08622 (9) | −0.17296 (10) | 0.0283 (3) | |
C25 | 0.46723 (15) | 0.10506 (10) | −0.08879 (11) | 0.0318 (3) | |
C26 | 0.42692 (15) | 0.10098 (9) | −0.00785 (11) | 0.0316 (3) | |
N31 | −0.35849 (13) | 0.38411 (9) | −0.01309 (10) | 0.0361 (3) | |
C32 | −0.45180 (16) | 0.32954 (11) | 0.00330 (12) | 0.0397 (4) | |
C33 | −0.59206 (16) | 0.33550 (10) | −0.03900 (12) | 0.0362 (4) | |
C34 | −0.64118 (15) | 0.40102 (9) | −0.10150 (10) | 0.0289 (3) | |
C35 | −0.54310 (15) | 0.45700 (10) | −0.11908 (10) | 0.0316 (3) | |
C36 | −0.40596 (16) | 0.44668 (10) | −0.07419 (11) | 0.0343 (3) | |
N41 | −1.36352 (13) | 0.18273 (9) | −0.24115 (9) | 0.0374 (3) | |
C42 | −1.38586 (16) | 0.26732 (11) | −0.24185 (12) | 0.0411 (4) | |
C43 | −1.28353 (15) | 0.32759 (11) | −0.23339 (11) | 0.0361 (4) | |
C44 | −1.14730 (14) | 0.30164 (10) | −0.22194 (10) | 0.0300 (3) | |
C45 | −1.12389 (15) | 0.21389 (10) | −0.22187 (12) | 0.0368 (4) | |
C46 | −1.23335 (16) | 0.15735 (11) | −0.23156 (12) | 0.0395 (4) | |
C51 | −0.79200 (15) | 0.41627 (10) | −0.14664 (12) | 0.0357 (4) | |
C52 | −0.88803 (14) | 0.33905 (10) | −0.16117 (11) | 0.0305 (3) | |
C53 | −1.03420 (15) | 0.36768 (10) | −0.21006 (12) | 0.0373 (4) | |
H14 | −0.1702 | 0.3856 | 0.0377 | 0.076* | |
H24 | 0.4832 | 0.1113 | −0.2461 | 0.053* | |
H12 | −0.0467 | 0.1163 | 0.0207 | 0.043* | |
H13 | −0.1762 | 0.2404 | 0.0078 | 0.045* | |
H15 | 0.1680 | 0.3747 | 0.1253 | 0.044* | |
H16 | 0.2966 | 0.2505 | 0.1405 | 0.041* | |
H22 | 0.1091 | 0.0394 | −0.0954 | 0.040* | |
H23 | 0.1760 | 0.0472 | −0.2303 | 0.039* | |
H25 | 0.5575 | 0.1204 | −0.0871 | 0.038* | |
H26 | 0.4896 | 0.1143 | 0.0482 | 0.038* | |
H32 | −0.4210 | 0.2853 | 0.0453 | 0.048* | |
H33 | −0.6530 | 0.2957 | −0.0255 | 0.043* | |
H35 | −0.5707 | 0.5014 | −0.1613 | 0.038* | |
H36 | −0.3426 | 0.4852 | −0.0869 | 0.041* | |
H42 | −1.4758 | 0.2864 | −0.2484 | 0.049* | |
H43 | −1.3052 | 0.3857 | −0.2353 | 0.043* | |
H45 | −1.0349 | 0.1931 | −0.2153 | 0.044* | |
H46 | −1.2153 | 0.0988 | −0.2314 | 0.047* | |
H51A | −0.7998 | 0.4424 | −0.2064 | 0.043* | |
H51B | −0.8255 | 0.4578 | −0.1096 | 0.043* | |
H52A | −0.8866 | 0.3135 | −0.1020 | 0.037* | |
H52B | −0.8571 | 0.2962 | −0.1981 | 0.037* | |
H53A | −1.0576 | 0.4158 | −0.1760 | 0.045* | |
H53B | −1.0340 | 0.3887 | −0.2708 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0331 (2) | 0.0354 (2) | 0.0339 (2) | 0.00144 (15) | 0.00938 (15) | 0.00827 (16) |
O11 | 0.0448 (7) | 0.0373 (7) | 0.0520 (7) | −0.0031 (5) | 0.0181 (6) | 0.0137 (5) |
O12 | 0.0387 (7) | 0.0569 (8) | 0.0331 (6) | 0.0067 (5) | 0.0043 (5) | 0.0092 (5) |
O14 | 0.0303 (6) | 0.0417 (7) | 0.0776 (10) | 0.0015 (5) | 0.0093 (6) | −0.0174 (6) |
O24 | 0.0280 (6) | 0.0423 (7) | 0.0369 (6) | −0.0026 (4) | 0.0110 (4) | −0.0053 (5) |
C11 | 0.0288 (8) | 0.0356 (9) | 0.0285 (8) | −0.0003 (6) | 0.0105 (6) | 0.0014 (6) |
C12 | 0.0319 (8) | 0.0343 (9) | 0.0408 (9) | −0.0052 (6) | 0.0101 (7) | −0.0045 (7) |
C13 | 0.0225 (8) | 0.0431 (10) | 0.0462 (10) | −0.0017 (6) | 0.0073 (6) | −0.0071 (7) |
C14 | 0.0313 (9) | 0.0372 (9) | 0.0401 (9) | 0.0003 (6) | 0.0123 (7) | −0.0082 (7) |
C15 | 0.0305 (8) | 0.0397 (9) | 0.0410 (9) | −0.0068 (6) | 0.0107 (6) | −0.0126 (7) |
C16 | 0.0256 (8) | 0.0454 (9) | 0.0309 (8) | −0.0031 (6) | 0.0074 (6) | −0.0042 (7) |
C21 | 0.0272 (8) | 0.0233 (7) | 0.0349 (8) | 0.0020 (5) | 0.0082 (6) | 0.0036 (6) |
C22 | 0.0266 (8) | 0.0335 (8) | 0.0400 (9) | −0.0058 (6) | 0.0075 (6) | 0.0019 (7) |
C23 | 0.0294 (8) | 0.0323 (8) | 0.0341 (8) | −0.0063 (6) | 0.0047 (6) | −0.0026 (6) |
C24 | 0.0280 (7) | 0.0219 (7) | 0.0354 (8) | 0.0028 (5) | 0.0094 (6) | −0.0014 (6) |
C25 | 0.0224 (7) | 0.0323 (8) | 0.0404 (9) | 0.0004 (5) | 0.0079 (6) | −0.0004 (7) |
C26 | 0.0264 (8) | 0.0297 (8) | 0.0356 (8) | 0.0012 (5) | 0.0031 (6) | −0.0001 (6) |
N31 | 0.0317 (7) | 0.0362 (8) | 0.0413 (8) | 0.0012 (5) | 0.0112 (6) | −0.0044 (6) |
C32 | 0.0371 (9) | 0.0350 (9) | 0.0470 (10) | 0.0047 (6) | 0.0111 (7) | 0.0065 (7) |
C33 | 0.0321 (8) | 0.0306 (8) | 0.0487 (10) | −0.0007 (6) | 0.0156 (7) | 0.0050 (7) |
C34 | 0.0304 (8) | 0.0261 (8) | 0.0323 (8) | −0.0009 (5) | 0.0122 (6) | −0.0037 (6) |
C35 | 0.0354 (8) | 0.0306 (8) | 0.0297 (8) | −0.0042 (6) | 0.0102 (6) | 0.0000 (6) |
C36 | 0.0336 (8) | 0.0361 (9) | 0.0355 (8) | −0.0076 (6) | 0.0135 (6) | −0.0058 (7) |
N41 | 0.0304 (7) | 0.0455 (8) | 0.0363 (8) | −0.0055 (5) | 0.0087 (5) | 0.0001 (6) |
C42 | 0.0276 (9) | 0.0489 (11) | 0.0472 (10) | 0.0024 (7) | 0.0108 (7) | −0.0039 (8) |
C43 | 0.0299 (8) | 0.0365 (9) | 0.0419 (9) | 0.0048 (6) | 0.0095 (6) | −0.0018 (7) |
C44 | 0.0286 (8) | 0.0340 (8) | 0.0275 (8) | 0.0012 (6) | 0.0077 (6) | 0.0024 (6) |
C45 | 0.0268 (8) | 0.0354 (9) | 0.0474 (10) | 0.0031 (6) | 0.0087 (7) | 0.0034 (7) |
C46 | 0.0361 (9) | 0.0348 (9) | 0.0453 (10) | 0.0003 (6) | 0.0069 (7) | 0.0039 (7) |
C51 | 0.0303 (8) | 0.0303 (8) | 0.0467 (10) | 0.0001 (6) | 0.0105 (7) | 0.0020 (7) |
C52 | 0.0290 (8) | 0.0295 (8) | 0.0344 (8) | 0.0008 (6) | 0.0107 (6) | 0.0011 (6) |
C53 | 0.0310 (8) | 0.0328 (9) | 0.0473 (10) | 0.0008 (6) | 0.0091 (7) | 0.0054 (7) |
S1—O11 | 1.4436 (12) | C25—C26 | 1.381 (2) |
S1—O12 | 1.4412 (12) | N31—C32 | 1.335 (2) |
S1—C11 | 1.7528 (16) | N31—C36 | 1.336 (2) |
S1—C21 | 1.7542 (15) | C32—C33 | 1.384 (2) |
O14—C14 | 1.3426 (19) | C33—C34 | 1.385 (2) |
O24—C24 | 1.3477 (18) | C34—C35 | 1.391 (2) |
C11—C12 | 1.398 (2) | C34—C51 | 1.502 (2) |
C11—C16 | 1.384 (2) | C35—C36 | 1.370 (2) |
C12—C13 | 1.379 (2) | N41—C42 | 1.336 (2) |
C13—C14 | 1.391 (2) | N41—C46 | 1.335 (2) |
C14—C15 | 1.396 (2) | C42—C43 | 1.372 (2) |
C15—C16 | 1.376 (2) | C43—C44 | 1.391 (2) |
C21—C22 | 1.391 (2) | C44—C45 | 1.387 (2) |
C21—C26 | 1.390 (2) | C44—C53 | 1.506 (2) |
C22—C23 | 1.373 (2) | C45—C46 | 1.384 (2) |
C23—C24 | 1.399 (2) | C51—C52 | 1.520 (2) |
C24—C25 | 1.392 (2) | C52—C53 | 1.521 (2) |
O11—S1—O12 | 119.04 (7) | C23—C24—C25 | 119.36 (14) |
O11—S1—C11 | 107.79 (7) | C24—C25—C26 | 120.18 (13) |
O11—S1—C21 | 108.57 (7) | C21—C26—C25 | 119.84 (14) |
O12—S1—C11 | 108.29 (7) | C32—N31—C36 | 116.90 (13) |
O12—S1—C21 | 107.67 (7) | N31—C32—C33 | 123.33 (15) |
C11—S1—C21 | 104.55 (7) | C32—C33—C34 | 119.66 (15) |
S1—C11—C12 | 120.06 (12) | C33—C34—C35 | 116.66 (14) |
S1—C11—C16 | 120.02 (11) | C33—C34—C51 | 123.75 (14) |
C12—C11—C16 | 119.84 (15) | C35—C34—C51 | 119.53 (13) |
C11—C12—C13 | 119.70 (14) | C34—C35—C36 | 120.05 (14) |
C12—C13—C14 | 120.42 (14) | N31—C36—C35 | 123.40 (14) |
O14—C14—C13 | 123.18 (14) | C42—N41—C46 | 116.75 (14) |
O14—C14—C15 | 117.23 (14) | N41—C42—C43 | 123.69 (14) |
C13—C14—C15 | 119.59 (15) | C42—C43—C44 | 119.89 (15) |
C14—C15—C16 | 119.99 (15) | C43—C44—C45 | 116.56 (14) |
C11—C16—C15 | 120.45 (14) | C45—C44—C53 | 123.45 (13) |
S1—C21—C22 | 119.59 (11) | C43—C44—C53 | 119.99 (14) |
S1—C21—C26 | 119.95 (12) | C44—C45—C46 | 119.85 (14) |
C22—C21—C26 | 120.39 (14) | N41—C46—C45 | 123.25 (15) |
C21—C22—C23 | 119.61 (13) | C34—C51—C52 | 117.57 (13) |
C22—C23—C24 | 120.60 (14) | C51—C52—C53 | 109.24 (12) |
O24—C24—C25 | 122.88 (13) | C44—C53—C52 | 117.08 (13) |
O24—C24—C23 | 117.76 (13) | ||
O12—S1—C11—C16 | 28.38 (15) | O24—C24—C25—C26 | 178.56 (13) |
O11—S1—C11—C16 | 158.40 (12) | C23—C24—C25—C26 | −1.7 (2) |
C21—S1—C11—C16 | −86.20 (13) | C24—C25—C26—C21 | 0.8 (2) |
O12—S1—C11—C12 | −154.85 (13) | C22—C21—C26—C25 | 0.5 (2) |
O11—S1—C11—C12 | −24.83 (15) | S1—C21—C26—C25 | −176.44 (11) |
C21—S1—C11—C12 | 90.57 (14) | C36—N31—C32—C33 | −0.4 (2) |
C16—C11—C12—C13 | −1.5 (2) | N31—C32—C33—C34 | −0.3 (3) |
S1—C11—C12—C13 | −178.32 (12) | C32—C33—C34—C35 | 1.1 (2) |
C11—C12—C13—C14 | 0.6 (2) | C32—C33—C34—C51 | −176.13 (16) |
C12—C13—C14—O14 | −178.89 (16) | C33—C34—C35—C36 | −1.1 (2) |
C12—C13—C14—C15 | 1.0 (3) | C51—C34—C35—C36 | 176.20 (14) |
O14—C14—C15—C16 | 178.27 (15) | C32—N31—C36—C35 | 0.4 (2) |
C13—C14—C15—C16 | −1.6 (3) | C34—C35—C36—N31 | 0.4 (2) |
C14—C15—C16—C11 | 0.7 (2) | C46—N41—C42—C43 | 0.0 (3) |
C12—C11—C16—C15 | 0.9 (2) | N41—C42—C43—C44 | −1.0 (3) |
S1—C11—C16—C15 | 177.70 (12) | C42—C43—C44—C45 | 1.4 (2) |
O12—S1—C21—C26 | −12.27 (14) | C42—C43—C44—C53 | −178.35 (15) |
O11—S1—C21—C26 | −142.40 (12) | C43—C44—C45—C46 | −0.9 (2) |
C11—S1—C21—C26 | 102.75 (13) | C53—C44—C45—C46 | 178.84 (15) |
O12—S1—C21—C22 | 170.74 (12) | C42—N41—C46—C45 | 0.5 (3) |
O11—S1—C21—C22 | 40.61 (14) | C44—C45—C46—N41 | −0.1 (3) |
C11—S1—C21—C22 | −74.24 (13) | C33—C34—C51—C52 | −28.8 (2) |
C26—C21—C22—C23 | −1.0 (2) | C35—C34—C51—C52 | 154.06 (14) |
S1—C21—C22—C23 | 176.02 (12) | C34—C51—C52—C53 | −178.32 (14) |
C21—C22—C23—C24 | 0.1 (2) | C45—C44—C53—C52 | −23.4 (2) |
C22—C23—C24—O24 | −178.99 (14) | C43—C44—C53—C52 | 156.27 (15) |
C22—C23—C24—C25 | 1.3 (2) | C51—C52—C53—C44 | −173.91 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N31 | 0.82 | 1.84 | 2.6514 (19) | 171 |
O24—H24···N41i | 0.82 | 1.88 | 2.6850 (18) | 166 |
C12—H12···O11ii | 0.93 | 2.54 | 3.428 (2) | 160 |
C26—H26···O12 | 0.93 | 2.52 | 2.903 (2) | 105 |
Symmetry codes: (i) x+2, y, z; (ii) −x, −y, −z. |
2(C13H27N2)·2(C12H9O4S)·H2O | ? #Insert any comments here. |
Mr = 939.25 | Dx = 1.267 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.7107 Å |
a = 12.2739 (10) Å | Cell parameters from 25 reflections |
b = 19.454 (2) Å | θ = 9.5–17.5° |
c = 20.6251 (13) Å | µ = 0.17 mm−1 |
V = 4924.7 (8) Å3 | T = 294 K |
Z = 4 | Plate, colourless |
F(000) = 2024 | 0.40 × 0.38 × 0.19 mm |
Enraf-Nonius CAD-4 diffractometer | 5888 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.019 |
Graphite monochromator | θmax = 25.2°, θmin = 2.1° |
θ/2θ scans | h = 0→14 |
Absorption correction: gaussian ABSO in NRCVAX (Gabe et al., 1989) | k = 0→23 |
Tmin = 0.943, Tmax = 0.972 | l = −24→24 |
9558 measured reflections | 3 standard reflections every 120 min |
8866 independent reflections | intensity decay: 2.2% |
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)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.103 | Calculated w = 1/[σ2(Fo2) + (0.0509P)2 + 0.2197P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
8866 reflections | Δρmax = 0.21 e Å−3 |
595 parameters | Δρmin = −0.17 e Å−3 |
2 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (6) |
2(C13H27N2)·2(C12H9O4S)·H2O | V = 4924.7 (8) Å3 |
Mr = 939.25 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 12.2739 (10) Å | µ = 0.17 mm−1 |
b = 19.454 (2) Å | T = 294 K |
c = 20.6251 (13) Å | 0.40 × 0.38 × 0.19 mm |
Enraf-Nonius CAD-4 diffractometer | 5888 reflections with I > 2σ(I) |
Absorption correction: gaussian ABSO in NRCVAX (Gabe et al., 1989) | Rint = 0.019 |
Tmin = 0.943, Tmax = 0.972 | 3 standard reflections every 120 min |
9558 measured reflections | intensity decay: 2.2% |
8866 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.103 | Δρmax = 0.21 e Å−3 |
S = 1.03 | Δρmin = −0.17 e Å−3 |
8866 reflections | Absolute structure: Flack (1983) |
595 parameters | Absolute structure parameter: 0.06 (6) |
2 restraints |
Experimental. ? #Insert any special details here. |
Geometry. The following mean-plane details are from the final SHELXL97 calculation Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 0.1032 (0.0174) x + 2.4128 (0.0418) y + 20.4651 (0.0060) z = 5.2240 (0.0129) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O12 Rms deviation of fitted atoms = 0.0000 11.4343 (0.0096) x + 6.9693 (0.0385) y - 1.2686 (0.0317) z = 1.4158 (0.0137) Angle to previous plane (with approximate e.s.d.) = 89.50 (13) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 3.3232 (0.0135) x - 15.7838 (0.0089) y - 10.6852 (0.0071) z = 1.0851 (0.0027) Angle to previous plane (with approximate e.s.d.) = 89.62 (12) * -0.0061 (0.0013) S1 * 0.0079 (0.0022) C11 * -0.0021 (0.0022) C12 * 0.0053 (0.0022) C13 * -0.0052 (0.0025) C14 * 0.0031 (0.0021) C15 * 0.0000 (0.0020) C16 * -0.0029 (0.0017) O14 Rms deviation of fitted atoms = 0.0047 11.4343 (0.0096) x + 6.9693 (0.0385) y - 1.2686 (0.0317) z = 1.4158 (0.0137) Angle to previous plane (with approximate e.s.d.) = 89.62 (12) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 2.0328 (0.0140) x - 14.0266 (0.0082) y + 13.8770 (0.0071) z = 7.1615 (0.0035) Angle to previous plane (with approximate e.s.d.) = 81.64 (12) * 0.0235 (0.0014) S1 * -0.0040 (0.0023) C21 * -0.0101 (0.0022) C22 * -0.0126 (0.0023) C23 * -0.0014 (0.0025) C24 * -0.0104 (0.0022) C25 * -0.0112 (0.0021) C26 * 0.0262 (0.0019) O24 Rms deviation of fitted atoms = 0.0148 ################################################################ 0.1379 (0.0168) x + 3.4946 (0.0388) y - 20.2883 (0.0078) z = 5.1854 (0.0095) * 0.0000 (0.0000) S2 * 0.0000 (0.0000) O21 * 0.0000 (0.0000) O22 Rms deviation of fitted atoms = 0.0000 - 11.3320 (0.0103) x - 7.3275 (0.0387) y - 1.5599 (0.0312) z = 2.0353 (0.0116) Angle to previous plane (with approximate e.s.d.) = 89.79 (12) * 0.0000 (0.0000) S2 * 0.0000 (0.0000) C31 * 0.0000 (0.0000) C41 Rms deviation of fitted atoms = 0.0000 - 3.7652 (0.0140) x + 15.9832 (0.0100) y - 9.9099 (0.0081) z = 6.4458 (0.0032) Angle to previous plane (with approximate e.s.d.) = 89.42 (12) * -0.0196 (0.0013) S2 * 0.0142 (0.0023) C31 * 0.0093 (0.0021) C32 * -0.0002 (0.0022) C33 * -0.0018 (0.0025) C34 * 0.0025 (0.0024) C35 * 0.0066 (0.0023) C36 * -0.0111 (0.0019) O34 Rms deviation of fitted atoms = 0.0103 - 11.3320 (0.0103) x - 7.3275 (0.0387) y - 1.5599 (0.0312) z = 2.0353 (0.0116) Angle to previous plane (with approximate e.s.d.) = 89.42 (12) * 0.0000 (0.0000) S2 * 0.0000 (0.0000) C31 * 0.0000 (0.0000) C41 Rms deviation of fitted atoms = 0.0000 - 5.0532 (0.0129) x + 10.8877 (0.0113) y + 14.8338 (0.0068) z = 0.2816 (0.0030) Angle to previous plane (with approximate e.s.d.) = 83.40 (11) * -0.0346 (0.0013) S2 * 0.0048 (0.0023) C41 * 0.0104 (0.0021) C42 * 0.0232 (0.0021) C43 * 0.0113 (0.0023) C44 * 0.0250 (0.0022) C45 * 0.0099 (0.0023) C46 * -0.0501 (0.0015) O44 Rms deviation of fitted atoms = 0.0256 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.27531 (7) | −0.19807 (4) | 0.27723 (3) | 0.0428 (2) | |
O11 | 0.39129 (18) | −0.21011 (11) | 0.27806 (10) | 0.0586 (6) | |
O12 | 0.2023 (2) | −0.25561 (9) | 0.28438 (10) | 0.0596 (6) | |
O14 | 0.16741 (18) | −0.05697 (11) | 0.03495 (9) | 0.0565 (6) | |
O24 | 0.1737 (2) | −0.00532 (13) | 0.48713 (11) | 0.0685 (7) | |
C11 | 0.2421 (2) | −0.15683 (14) | 0.20468 (13) | 0.0364 (7) | |
C12 | 0.3215 (3) | −0.11791 (15) | 0.17283 (13) | 0.0453 (7) | |
C13 | 0.2968 (3) | −0.08503 (15) | 0.11587 (15) | 0.0480 (8) | |
C14 | 0.1922 (3) | −0.08812 (14) | 0.08887 (13) | 0.0409 (7) | |
C15 | 0.1145 (3) | −0.12753 (14) | 0.12217 (13) | 0.0418 (7) | |
C16 | 0.1382 (2) | −0.16106 (14) | 0.17936 (13) | 0.0389 (7) | |
C21 | 0.2462 (2) | −0.13902 (14) | 0.33920 (13) | 0.0378 (7) | |
C22 | 0.1404 (3) | −0.13217 (15) | 0.36118 (13) | 0.0443 (8) | |
C23 | 0.1170 (3) | −0.08660 (16) | 0.41049 (14) | 0.0496 (8) | |
C24 | 0.1998 (3) | −0.04747 (15) | 0.43871 (13) | 0.0458 (8) | |
C25 | 0.3053 (3) | −0.05465 (15) | 0.41536 (13) | 0.0448 (8) | |
C26 | 0.3280 (3) | −0.09989 (15) | 0.36626 (13) | 0.0418 (7) | |
S2 | −0.27711 (7) | 0.19832 (4) | −0.22331 (3) | 0.0440 (2) | |
O21 | −0.39419 (18) | 0.20863 (11) | −0.22233 (9) | 0.0564 (6) | |
O22 | −0.2095 (2) | 0.25765 (9) | −0.21263 (10) | 0.0614 (6) | |
O34 | −0.16266 (19) | 0.07174 (13) | −0.47181 (10) | 0.0632 (6) | |
O44 | −0.17196 (17) | −0.01457 (10) | −0.03228 (8) | 0.0462 (5) | |
C31 | −0.2431 (2) | 0.16176 (14) | −0.29861 (14) | 0.0376 (7) | |
C32 | −0.3202 (3) | 0.12321 (14) | −0.33100 (13) | 0.0432 (7) | |
C33 | −0.2951 (3) | 0.09254 (15) | −0.38903 (14) | 0.0454 (8) | |
C34 | −0.1921 (3) | 0.10021 (15) | −0.41563 (14) | 0.0442 (8) | |
C35 | −0.1154 (3) | 0.13890 (16) | −0.38281 (15) | 0.0510 (8) | |
C36 | −0.1403 (3) | 0.16956 (16) | −0.32433 (14) | 0.0497 (8) | |
C41 | −0.2454 (2) | 0.13672 (14) | −0.16463 (13) | 0.0384 (7) | |
C42 | −0.1469 (2) | 0.13835 (15) | −0.13192 (13) | 0.0420 (7) | |
C43 | −0.1235 (2) | 0.08859 (15) | −0.08654 (14) | 0.0424 (7) | |
C44 | −0.1968 (2) | 0.03495 (14) | −0.07293 (12) | 0.0372 (7) | |
C45 | −0.2962 (3) | 0.03531 (15) | −0.10615 (14) | 0.0477 (8) | |
C46 | −0.3194 (3) | 0.08507 (15) | −0.15161 (14) | 0.0478 (8) | |
N51 | 0.0012 (2) | 0.06171 (12) | 0.20704 (11) | 0.0545 (7) | |
C52 | 0.0786 (3) | 0.01648 (16) | 0.23892 (15) | 0.0572 (10) | |
C53 | 0.1457 (3) | 0.05840 (16) | 0.28533 (15) | 0.0516 (8) | |
C54 | 0.0781 (2) | 0.09618 (15) | 0.33613 (13) | 0.0436 (7) | |
C55 | −0.0124 (3) | 0.13589 (14) | 0.30235 (14) | 0.0494 (8) | |
C56 | −0.0748 (3) | 0.09270 (17) | 0.25382 (16) | 0.0555 (9) | |
C57 | 0.1501 (3) | 0.14114 (16) | 0.37901 (15) | 0.0543 (9) | |
C58 | 0.0948 (3) | 0.17584 (17) | 0.43601 (16) | 0.0608 (9) | |
C59 | 0.1745 (3) | 0.21886 (16) | 0.47515 (14) | 0.0523 (8) | |
N61 | 0.0841 (2) | 0.38003 (12) | 0.60938 (12) | 0.0496 (7) | |
C62 | −0.0067 (3) | 0.34366 (16) | 0.57560 (15) | 0.0563 (9) | |
C63 | 0.0360 (3) | 0.30414 (16) | 0.51834 (14) | 0.0528 (8) | |
C64 | 0.1274 (3) | 0.25476 (15) | 0.53502 (14) | 0.0469 (8) | |
C65 | 0.2144 (3) | 0.29273 (16) | 0.57249 (14) | 0.0526 (8) | |
C66 | 0.1715 (3) | 0.33153 (17) | 0.63008 (15) | 0.0572 (9) | |
N71 | −0.0132 (2) | 0.45270 (13) | −0.28815 (12) | 0.0592 (7) | |
C72 | 0.0591 (4) | 0.50063 (19) | −0.25359 (17) | 0.0739 (13) | |
C73 | 0.1334 (3) | 0.46272 (17) | −0.21021 (16) | 0.0608 (9) | |
C74 | 0.0745 (3) | 0.41753 (16) | −0.16111 (15) | 0.0544 (9) | |
C75 | −0.0042 (3) | 0.37162 (18) | −0.19824 (18) | 0.0705 (10) | |
C76 | −0.0766 (3) | 0.4111 (2) | −0.2419 (2) | 0.0807 (13) | |
C77 | 0.1535 (3) | 0.37766 (16) | −0.11958 (14) | 0.0583 (9) | |
C78 | 0.1011 (3) | 0.32636 (18) | −0.07305 (17) | 0.0677 (10) | |
C79 | 0.1823 (3) | 0.28940 (16) | −0.03086 (14) | 0.0594 (9) | |
N81 | 0.0933 (3) | 0.16182 (14) | 0.13118 (12) | 0.0607 (8) | |
C82 | 0.0029 (3) | 0.19326 (16) | 0.09429 (15) | 0.0585 (9) | |
C83 | 0.0439 (3) | 0.25142 (17) | 0.05200 (15) | 0.0596 (9) | |
C84 | 0.1372 (3) | 0.23045 (15) | 0.00811 (14) | 0.0496 (8) | |
C85 | 0.2255 (3) | 0.19450 (17) | 0.04827 (15) | 0.0564 (8) | |
C86 | 0.1835 (3) | 0.13743 (16) | 0.08988 (17) | 0.0590 (9) | |
O9 | −0.0152 (2) | 0.02220 (13) | 0.05933 (12) | 0.0636 (7) | |
H24 | 0.2295 | 0.0091 | 0.5043 | 0.103* | |
H12 | 0.3912 | −0.1143 | 0.1903 | 0.054* | |
H13 | 0.3508 | −0.0601 | 0.0947 | 0.058* | |
H15 | 0.0447 | −0.1312 | 0.1051 | 0.050* | |
H16 | 0.0847 | −0.1863 | 0.2007 | 0.047* | |
H22 | 0.0850 | −0.1583 | 0.3427 | 0.053* | |
H23 | 0.0456 | −0.0819 | 0.4250 | 0.060* | |
H25 | 0.3612 | −0.0285 | 0.4332 | 0.054* | |
H26 | 0.3990 | −0.1042 | 0.3511 | 0.050* | |
H34 | −0.2140 | 0.0500 | −0.4868 | 0.095* | |
H32 | −0.3895 | 0.1180 | −0.3134 | 0.052* | |
H33 | −0.3474 | 0.0665 | −0.4106 | 0.054* | |
H35 | −0.0462 | 0.1443 | −0.4004 | 0.061* | |
H36 | −0.0880 | 0.1953 | −0.3025 | 0.060* | |
H42 | −0.0968 | 0.1730 | −0.1406 | 0.050* | |
H43 | −0.0576 | 0.0905 | −0.0644 | 0.051* | |
H45 | −0.3475 | 0.0014 | −0.0974 | 0.057* | |
H46 | −0.3855 | 0.0839 | −0.1737 | 0.057* | |
H51 | −0.0368 | 0.0376 | 0.1774 | 0.065* | |
H52A | 0.1255 | −0.0050 | 0.2070 | 0.069* | |
H52B | 0.0401 | −0.0194 | 0.2622 | 0.069* | |
H53A | 0.1876 | 0.0918 | 0.2609 | 0.062* | |
H53B | 0.1968 | 0.0283 | 0.3072 | 0.062* | |
H54 | 0.0438 | 0.0615 | 0.3639 | 0.052* | |
H55A | −0.0628 | 0.1532 | 0.3347 | 0.059* | |
H55B | 0.0190 | 0.1751 | 0.2802 | 0.059* | |
H56A | −0.1144 | 0.0568 | 0.2763 | 0.067* | |
H56B | −0.1271 | 0.1212 | 0.2311 | 0.067* | |
H57A | 0.2090 | 0.1129 | 0.3956 | 0.065* | |
H57B | 0.1825 | 0.1765 | 0.3521 | 0.065* | |
H58A | 0.0628 | 0.1411 | 0.4638 | 0.073* | |
H58B | 0.0366 | 0.2051 | 0.4202 | 0.073* | |
H59A | 0.2053 | 0.2536 | 0.4468 | 0.063* | |
H59B | 0.2338 | 0.1894 | 0.4891 | 0.063* | |
H61A | 0.1126 | 0.4118 | 0.5826 | 0.060* | |
H61B | 0.0575 | 0.4020 | 0.6444 | 0.060* | |
H62A | −0.0603 | 0.3769 | 0.5611 | 0.068* | |
H62B | −0.0421 | 0.3123 | 0.6055 | 0.068* | |
H63A | 0.0621 | 0.3365 | 0.4861 | 0.063* | |
H63B | −0.0235 | 0.2784 | 0.4991 | 0.063* | |
H64 | 0.0973 | 0.2192 | 0.5635 | 0.056* | |
H65A | 0.2685 | 0.2599 | 0.5872 | 0.063* | |
H65B | 0.2505 | 0.3248 | 0.5436 | 0.063* | |
H66A | 0.1425 | 0.2994 | 0.6617 | 0.069* | |
H66B | 0.2303 | 0.3570 | 0.6503 | 0.069* | |
H71 | −0.0590 | 0.4766 | −0.3138 | 0.071* | |
H72A | 0.0157 | 0.5326 | −0.2284 | 0.089* | |
H72B | 0.1012 | 0.5269 | −0.2847 | 0.089* | |
H73A | 0.1786 | 0.4955 | −0.1871 | 0.073* | |
H73B | 0.1811 | 0.4341 | −0.2363 | 0.073* | |
H74 | 0.0317 | 0.4475 | −0.1326 | 0.065* | |
H75A | 0.0371 | 0.3388 | −0.2237 | 0.085* | |
H75B | −0.0483 | 0.3460 | −0.1676 | 0.085* | |
H76A | −0.1232 | 0.3796 | −0.2655 | 0.097* | |
H76B | −0.1228 | 0.4411 | −0.2162 | 0.097* | |
H77A | 0.1964 | 0.4100 | −0.0945 | 0.070* | |
H77B | 0.2031 | 0.3530 | −0.1478 | 0.070* | |
H78A | 0.0498 | 0.3506 | −0.0455 | 0.081* | |
H78B | 0.0606 | 0.2927 | −0.0980 | 0.081* | |
H79A | 0.2142 | 0.3224 | −0.0012 | 0.071* | |
H79B | 0.2404 | 0.2721 | −0.0582 | 0.071* | |
H81A | 0.1194 | 0.1929 | 0.1595 | 0.073* | |
H81B | 0.0671 | 0.1261 | 0.1542 | 0.073* | |
H82A | −0.0514 | 0.2107 | 0.1242 | 0.070* | |
H82B | −0.0313 | 0.1586 | 0.0673 | 0.070* | |
H83A | 0.0677 | 0.2889 | 0.0796 | 0.072* | |
H83B | −0.0158 | 0.2682 | 0.0255 | 0.072* | |
H84 | 0.1086 | 0.1966 | −0.0227 | 0.060* | |
H85A | 0.2802 | 0.1762 | 0.0191 | 0.068* | |
H85B | 0.2607 | 0.2283 | 0.0758 | 0.068* | |
H86A | 0.1582 | 0.1001 | 0.0626 | 0.071* | |
H86B | 0.2420 | 0.1201 | 0.1170 | 0.071* | |
H91 | −0.058 (3) | 0.013 (2) | 0.0217 (16) | 0.095 (10)* | |
H92 | 0.032 (3) | −0.0045 (19) | 0.0453 (19) | 0.095 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0533 (5) | 0.0350 (4) | 0.0401 (4) | 0.0042 (4) | −0.0068 (4) | 0.0002 (3) |
O11 | 0.0546 (16) | 0.0626 (14) | 0.0585 (14) | 0.0246 (12) | −0.0104 (12) | −0.0027 (12) |
O12 | 0.0861 (18) | 0.0347 (11) | 0.0580 (13) | −0.0075 (11) | −0.0108 (13) | 0.0066 (10) |
O14 | 0.0568 (15) | 0.0703 (14) | 0.0425 (12) | −0.0008 (12) | −0.0057 (11) | 0.0138 (11) |
O24 | 0.0632 (17) | 0.0840 (17) | 0.0585 (14) | 0.0019 (15) | 0.0008 (13) | −0.0266 (13) |
C11 | 0.044 (2) | 0.0349 (15) | 0.0305 (15) | 0.0012 (14) | −0.0024 (13) | −0.0069 (13) |
C12 | 0.0364 (19) | 0.0537 (18) | 0.0458 (17) | −0.0039 (16) | −0.0050 (15) | −0.0014 (15) |
C13 | 0.041 (2) | 0.0555 (19) | 0.0473 (18) | −0.0050 (16) | 0.0041 (16) | 0.0071 (15) |
C14 | 0.045 (2) | 0.0434 (16) | 0.0347 (15) | 0.0015 (15) | −0.0011 (15) | 0.0000 (13) |
C15 | 0.037 (2) | 0.0501 (17) | 0.0386 (16) | −0.0019 (15) | −0.0037 (14) | −0.0058 (15) |
C16 | 0.0361 (18) | 0.0414 (16) | 0.0390 (16) | −0.0060 (15) | 0.0006 (14) | −0.0040 (13) |
C21 | 0.041 (2) | 0.0408 (16) | 0.0315 (15) | 0.0015 (14) | −0.0032 (13) | 0.0014 (13) |
C22 | 0.047 (2) | 0.0459 (17) | 0.0398 (16) | −0.0101 (16) | −0.0078 (15) | −0.0018 (14) |
C23 | 0.039 (2) | 0.064 (2) | 0.0453 (18) | −0.0025 (17) | 0.0017 (15) | −0.0018 (17) |
C24 | 0.053 (2) | 0.0500 (18) | 0.0342 (15) | 0.0028 (16) | −0.0022 (15) | −0.0024 (14) |
C25 | 0.042 (2) | 0.0524 (18) | 0.0395 (16) | −0.0050 (15) | −0.0096 (15) | −0.0033 (14) |
C26 | 0.0403 (19) | 0.0513 (17) | 0.0336 (14) | 0.0006 (16) | −0.0048 (14) | 0.0005 (13) |
S2 | 0.0561 (6) | 0.0374 (4) | 0.0384 (4) | 0.0101 (4) | −0.0063 (4) | −0.0011 (4) |
O21 | 0.0538 (15) | 0.0675 (15) | 0.0480 (13) | 0.0297 (12) | −0.0044 (11) | 0.0026 (12) |
O22 | 0.0981 (19) | 0.0309 (11) | 0.0552 (13) | −0.0049 (12) | −0.0142 (14) | −0.0027 (10) |
O34 | 0.0583 (16) | 0.0816 (17) | 0.0498 (13) | −0.0009 (13) | 0.0078 (12) | −0.0133 (12) |
O44 | 0.0534 (14) | 0.0454 (11) | 0.0397 (11) | 0.0014 (10) | −0.0089 (10) | 0.0076 (9) |
C31 | 0.040 (2) | 0.0372 (15) | 0.0352 (16) | 0.0009 (14) | −0.0046 (13) | 0.0028 (14) |
C32 | 0.0373 (19) | 0.0500 (18) | 0.0422 (16) | 0.0030 (15) | −0.0018 (14) | 0.0012 (14) |
C33 | 0.046 (2) | 0.0480 (17) | 0.0421 (17) | 0.0001 (16) | −0.0059 (16) | −0.0027 (14) |
C34 | 0.049 (2) | 0.0483 (17) | 0.0350 (15) | 0.0079 (16) | −0.0001 (16) | 0.0019 (14) |
C35 | 0.039 (2) | 0.065 (2) | 0.0499 (19) | −0.0093 (17) | 0.0052 (16) | 0.0011 (17) |
C36 | 0.047 (2) | 0.0557 (19) | 0.0469 (18) | −0.0111 (17) | −0.0075 (16) | 0.0015 (15) |
C41 | 0.046 (2) | 0.0369 (16) | 0.0325 (15) | 0.0053 (14) | −0.0023 (13) | −0.0019 (13) |
C42 | 0.037 (2) | 0.0425 (17) | 0.0465 (17) | −0.0033 (14) | −0.0024 (15) | 0.0004 (14) |
C43 | 0.0358 (19) | 0.0506 (18) | 0.0409 (17) | 0.0014 (15) | −0.0062 (14) | −0.0009 (15) |
C44 | 0.0406 (19) | 0.0397 (16) | 0.0315 (14) | 0.0071 (14) | −0.0019 (13) | −0.0032 (12) |
C45 | 0.045 (2) | 0.0457 (17) | 0.0528 (18) | −0.0076 (15) | −0.0043 (16) | 0.0012 (14) |
C46 | 0.0405 (19) | 0.056 (2) | 0.0470 (17) | −0.0026 (16) | −0.0129 (16) | 0.0020 (15) |
N51 | 0.066 (2) | 0.0460 (14) | 0.0518 (15) | −0.0097 (15) | −0.0123 (14) | −0.0032 (12) |
C52 | 0.071 (3) | 0.0428 (18) | 0.058 (2) | 0.0011 (18) | 0.0022 (19) | −0.0070 (16) |
C53 | 0.046 (2) | 0.0519 (17) | 0.0564 (19) | 0.0085 (16) | 0.0006 (16) | 0.0069 (16) |
C54 | 0.0445 (19) | 0.0422 (16) | 0.0441 (16) | 0.0010 (15) | 0.0041 (15) | 0.0028 (14) |
C55 | 0.046 (2) | 0.0443 (16) | 0.0582 (18) | 0.0022 (15) | 0.0022 (16) | 0.0002 (14) |
C56 | 0.041 (2) | 0.055 (2) | 0.071 (2) | −0.0044 (18) | −0.0064 (17) | 0.0099 (18) |
C57 | 0.053 (2) | 0.0535 (19) | 0.0560 (19) | −0.0044 (17) | −0.0001 (17) | −0.0022 (16) |
C58 | 0.064 (2) | 0.060 (2) | 0.059 (2) | −0.0111 (18) | 0.0044 (18) | −0.0080 (16) |
C59 | 0.054 (2) | 0.0536 (19) | 0.0492 (18) | 0.0008 (17) | −0.0046 (17) | 0.0036 (15) |
N61 | 0.0531 (18) | 0.0459 (15) | 0.0498 (15) | −0.0001 (13) | −0.0034 (13) | 0.0020 (12) |
C62 | 0.048 (2) | 0.0551 (19) | 0.066 (2) | −0.0022 (17) | −0.0121 (17) | 0.0024 (17) |
C63 | 0.054 (2) | 0.0531 (18) | 0.0517 (17) | −0.0030 (18) | −0.0126 (16) | −0.0005 (16) |
C64 | 0.060 (2) | 0.0400 (16) | 0.0409 (16) | −0.0055 (16) | −0.0021 (16) | 0.0077 (13) |
C65 | 0.050 (2) | 0.0542 (19) | 0.0539 (18) | 0.0103 (17) | −0.0132 (16) | 0.0054 (16) |
C66 | 0.054 (2) | 0.060 (2) | 0.058 (2) | 0.0104 (18) | −0.0146 (17) | 0.0011 (17) |
N71 | 0.064 (2) | 0.0603 (16) | 0.0537 (16) | −0.0011 (15) | −0.0090 (15) | 0.0080 (13) |
C72 | 0.096 (4) | 0.059 (2) | 0.067 (2) | −0.008 (2) | 0.004 (2) | 0.0018 (19) |
C73 | 0.065 (2) | 0.0525 (19) | 0.065 (2) | −0.0159 (18) | −0.0055 (19) | 0.0050 (17) |
C74 | 0.058 (2) | 0.0506 (19) | 0.0543 (19) | −0.0060 (17) | 0.0040 (17) | 0.0022 (16) |
C75 | 0.056 (2) | 0.065 (2) | 0.090 (3) | −0.012 (2) | −0.003 (2) | 0.022 (2) |
C76 | 0.063 (3) | 0.079 (3) | 0.100 (3) | −0.003 (2) | −0.011 (2) | 0.014 (2) |
C77 | 0.071 (3) | 0.059 (2) | 0.0446 (17) | −0.0059 (19) | 0.0023 (17) | 0.0038 (16) |
C78 | 0.074 (3) | 0.069 (2) | 0.060 (2) | 0.005 (2) | 0.013 (2) | 0.0151 (18) |
C79 | 0.075 (3) | 0.059 (2) | 0.0444 (17) | −0.0036 (19) | 0.0034 (18) | 0.0025 (16) |
N81 | 0.090 (2) | 0.0503 (16) | 0.0419 (15) | −0.0134 (16) | 0.0039 (15) | 0.0059 (13) |
C82 | 0.063 (2) | 0.0523 (18) | 0.0596 (19) | 0.0058 (19) | 0.0120 (18) | 0.0031 (17) |
C83 | 0.076 (3) | 0.0559 (19) | 0.0472 (18) | 0.0020 (19) | 0.0121 (18) | 0.0027 (15) |
C84 | 0.061 (2) | 0.0453 (18) | 0.0428 (17) | −0.0014 (16) | 0.0031 (16) | −0.0034 (14) |
C85 | 0.061 (2) | 0.0568 (19) | 0.0518 (18) | −0.0027 (19) | 0.0062 (17) | −0.0014 (16) |
C86 | 0.054 (2) | 0.056 (2) | 0.067 (2) | 0.0025 (18) | −0.0023 (19) | 0.0017 (17) |
O9 | 0.0613 (17) | 0.0634 (15) | 0.0659 (15) | −0.0018 (14) | −0.0165 (13) | −0.0049 (12) |
S1—O11 | 1.443 (2) | C44—C45 | 1.400 (4) |
S1—O12 | 1.441 (2) | C45—C46 | 1.378 (4) |
S1—C11 | 1.746 (3) | N51—C52 | 1.453 (4) |
S1—C21 | 1.755 (3) | N51—C56 | 1.471 (4) |
O14—C14 | 1.302 (3) | C52—C53 | 1.503 (4) |
O24—C24 | 1.331 (3) | C53—C54 | 1.525 (4) |
C11—C12 | 1.398 (4) | C54—C55 | 1.522 (4) |
C11—C16 | 1.380 (4) | C54—C57 | 1.526 (4) |
C12—C13 | 1.371 (4) | C55—C56 | 1.514 (4) |
C13—C14 | 1.402 (4) | C57—C58 | 1.516 (4) |
C14—C15 | 1.402 (4) | C58—C59 | 1.520 (4) |
C15—C16 | 1.379 (4) | C59—C64 | 1.532 (4) |
C21—C22 | 1.382 (4) | N61—C62 | 1.492 (4) |
C21—C26 | 1.378 (4) | N61—C66 | 1.491 (4) |
C22—C23 | 1.379 (4) | C62—C63 | 1.503 (4) |
C23—C24 | 1.397 (4) | C63—C64 | 1.516 (4) |
C24—C25 | 1.388 (4) | C64—C65 | 1.511 (4) |
C25—C26 | 1.370 (4) | C65—C66 | 1.503 (4) |
S2—O21 | 1.451 (2) | N71—C72 | 1.472 (4) |
S2—O22 | 1.438 (2) | N71—C76 | 1.474 (4) |
S2—C31 | 1.758 (3) | C72—C73 | 1.476 (5) |
S2—C41 | 1.747 (3) | C73—C74 | 1.524 (4) |
O34—C34 | 1.334 (3) | C74—C77 | 1.508 (4) |
O44—C44 | 1.313 (3) | C74—C75 | 1.522 (4) |
C31—C32 | 1.380 (4) | C75—C76 | 1.480 (5) |
C31—C36 | 1.377 (4) | C77—C78 | 1.526 (4) |
C32—C33 | 1.372 (4) | C78—C79 | 1.505 (5) |
C33—C34 | 1.386 (4) | C79—C84 | 1.506 (4) |
C34—C35 | 1.383 (4) | N81—C82 | 1.477 (4) |
C35—C36 | 1.380 (4) | N81—C86 | 1.476 (4) |
C41—C42 | 1.384 (4) | C82—C83 | 1.514 (4) |
C41—C46 | 1.381 (4) | C83—C84 | 1.516 (4) |
C42—C43 | 1.377 (4) | C84—C85 | 1.532 (4) |
C43—C44 | 1.406 (4) | C85—C86 | 1.495 (4) |
O11—S1—O12 | 119.08 (14) | C41—C42—C43 | 119.8 (3) |
O11—S1—C11 | 108.36 (14) | C42—C43—C44 | 121.6 (3) |
O11—S1—C21 | 107.36 (14) | C43—C44—C45 | 117.2 (3) |
O12—S1—C11 | 107.43 (13) | O44—C44—C43 | 121.6 (3) |
O12—S1—C21 | 107.89 (14) | O44—C44—C45 | 121.2 (3) |
C11—S1—C21 | 106.01 (13) | C44—C45—C46 | 121.1 (3) |
S1—C11—C12 | 119.3 (2) | C41—C46—C45 | 120.5 (3) |
S1—C11—C16 | 120.8 (2) | C52—N51—C56 | 111.5 (2) |
C12—C11—C16 | 119.9 (3) | N51—C52—C53 | 108.6 (3) |
C11—C12—C13 | 120.1 (3) | C52—C53—C54 | 113.6 (3) |
C12—C13—C14 | 121.5 (3) | C53—C54—C55 | 109.1 (2) |
C13—C14—C15 | 116.8 (3) | C53—C54—C57 | 111.0 (3) |
O14—C14—C13 | 122.2 (3) | C55—C54—C57 | 113.4 (2) |
O14—C14—C15 | 120.9 (3) | C54—C55—C56 | 112.9 (2) |
C14—C15—C16 | 122.3 (3) | N51—C56—C55 | 109.9 (3) |
C11—C16—C15 | 119.4 (3) | C54—C57—C58 | 116.5 (3) |
S1—C21—C22 | 119.6 (2) | C57—C58—C59 | 111.7 (3) |
S1—C21—C26 | 120.6 (2) | C58—C59—C64 | 115.8 (3) |
C22—C21—C26 | 119.9 (3) | C62—N61—C66 | 111.8 (2) |
C21—C22—C23 | 120.0 (3) | N61—C62—C63 | 110.4 (3) |
C22—C23—C24 | 120.4 (3) | C62—C63—C64 | 113.8 (2) |
O24—C24—C23 | 118.2 (3) | C59—C64—C63 | 112.7 (2) |
O24—C24—C25 | 123.1 (3) | C59—C64—C65 | 111.6 (3) |
C23—C24—C25 | 118.6 (3) | C63—C64—C65 | 109.2 (2) |
C24—C25—C26 | 120.7 (3) | C64—C65—C66 | 113.7 (3) |
C21—C26—C25 | 120.4 (3) | N61—C66—C65 | 110.1 (2) |
O21—S2—O22 | 117.27 (15) | C72—N71—C76 | 110.6 (3) |
O21—S2—C31 | 107.65 (13) | N71—C72—C73 | 110.5 (3) |
O21—S2—C41 | 107.82 (14) | C72—C73—C74 | 113.4 (3) |
O22—S2—C31 | 108.84 (14) | C73—C74—C75 | 107.8 (3) |
O22—S2—C41 | 108.40 (13) | C73—C74—C77 | 111.7 (3) |
C31—S2—C41 | 106.35 (13) | C75—C74—C77 | 113.1 (3) |
S2—C31—C32 | 119.0 (2) | C74—C75—C76 | 112.5 (3) |
S2—C31—C36 | 120.9 (2) | N71—C76—C75 | 111.2 (3) |
C32—C31—C36 | 120.1 (3) | C74—C77—C78 | 115.0 (3) |
C31—C32—C33 | 120.3 (3) | C77—C78—C79 | 113.4 (3) |
C32—C33—C34 | 120.2 (3) | C78—C79—C84 | 115.4 (3) |
C33—C34—C35 | 119.1 (3) | C82—N81—C86 | 113.5 (2) |
O34—C34—C35 | 117.8 (3) | N81—C82—C83 | 110.9 (3) |
O34—C34—C33 | 123.1 (3) | C82—C83—C84 | 113.2 (3) |
C34—C35—C36 | 120.8 (3) | C79—C84—C83 | 113.0 (3) |
C31—C36—C35 | 119.5 (3) | C79—C84—C85 | 112.1 (3) |
S2—C41—C42 | 121.1 (2) | C83—C84—C85 | 109.5 (3) |
S2—C41—C46 | 119.1 (2) | C84—C85—C86 | 114.0 (3) |
C42—C41—C46 | 119.8 (3) | N81—C86—C85 | 110.6 (3) |
O12—S1—C11—C16 | 26.2 (3) | C46—C41—C42—C43 | −0.1 (4) |
O11—S1—C11—C16 | 156.1 (2) | S2—C41—C42—C43 | −179.1 (2) |
C21—S1—C11—C16 | −89.0 (2) | C41—C42—C43—C44 | 0.9 (4) |
O12—S1—C11—C12 | −155.2 (2) | C42—C43—C44—O44 | 176.2 (3) |
O11—S1—C11—C12 | −25.3 (3) | C42—C43—C44—C45 | −1.8 (4) |
C21—S1—C11—C12 | 89.6 (2) | O44—C44—C45—C46 | −176.1 (3) |
C16—C11—C12—C13 | −1.2 (4) | C43—C44—C45—C46 | 1.9 (4) |
S1—C11—C12—C13 | −179.8 (2) | C44—C45—C46—C41 | −1.2 (5) |
C11—C12—C13—C14 | 1.3 (5) | C42—C41—C46—C45 | 0.2 (4) |
C12—C13—C14—O14 | 179.8 (3) | S2—C41—C46—C45 | 179.2 (2) |
C12—C13—C14—C15 | −1.2 (4) | C56—N51—C52—C53 | −62.4 (3) |
O14—C14—C15—C16 | −180.0 (3) | N51—C52—C53—C54 | 57.7 (4) |
C13—C14—C15—C16 | 1.0 (4) | C52—C53—C54—C55 | −50.8 (3) |
C14—C15—C16—C11 | −0.9 (4) | C52—C53—C54—C57 | −176.5 (3) |
C12—C11—C16—C15 | 1.0 (4) | C53—C54—C55—C56 | 48.7 (3) |
S1—C11—C16—C15 | 179.6 (2) | C57—C54—C55—C56 | 173.1 (3) |
O12—S1—C21—C26 | 146.6 (2) | C52—N51—C56—C55 | 61.4 (3) |
O11—S1—C21—C26 | 17.1 (3) | C54—C55—C56—N51 | −54.5 (3) |
C11—S1—C21—C26 | −98.5 (2) | C55—C54—C57—C58 | 62.9 (4) |
O12—S1—C21—C22 | −33.0 (3) | C53—C54—C57—C58 | −173.9 (3) |
O11—S1—C21—C22 | −162.5 (2) | C54—C57—C58—C59 | 179.8 (3) |
C11—S1—C21—C22 | 81.9 (3) | C57—C58—C59—C64 | −178.5 (3) |
C26—C21—C22—C23 | −0.5 (4) | C66—N61—C62—C63 | −56.6 (3) |
S1—C21—C22—C23 | 179.1 (2) | N61—C62—C63—C64 | 54.5 (3) |
C21—C22—C23—C24 | −0.4 (4) | C62—C63—C64—C65 | −51.5 (4) |
C22—C23—C24—O24 | −178.5 (3) | C62—C63—C64—C59 | −176.1 (3) |
C22—C23—C24—C25 | 1.1 (4) | C58—C59—C64—C65 | 176.8 (3) |
O24—C24—C25—C26 | 178.6 (3) | C58—C59—C64—C63 | −59.9 (4) |
C23—C24—C25—C26 | −0.9 (4) | C63—C64—C65—C66 | 52.1 (3) |
C24—C25—C26—C21 | 0.0 (4) | C59—C64—C65—C66 | 177.4 (2) |
C22—C21—C26—C25 | 0.7 (4) | C62—N61—C66—C65 | 57.1 (3) |
S1—C21—C26—C25 | −178.9 (2) | C64—C65—C66—N61 | −55.7 (4) |
O22—S2—C31—C36 | 27.0 (3) | C76—N71—C72—C73 | 58.0 (4) |
O21—S2—C31—C36 | 155.1 (2) | N71—C72—C73—C74 | −56.9 (4) |
C41—S2—C31—C36 | −89.6 (3) | C72—C73—C74—C77 | 177.8 (3) |
O22—S2—C31—C32 | −154.8 (2) | C72—C73—C74—C75 | 53.0 (4) |
O21—S2—C31—C32 | −26.8 (3) | C77—C74—C75—C76 | −176.5 (3) |
C41—S2—C31—C32 | 88.6 (2) | C73—C74—C75—C76 | −52.5 (4) |
C36—C31—C32—C33 | −0.1 (4) | C72—N71—C76—C75 | −58.5 (4) |
S2—C31—C32—C33 | −178.3 (2) | C74—C75—C76—N71 | 57.0 (4) |
C31—C32—C33—C34 | −0.1 (4) | C75—C74—C77—C78 | −53.1 (4) |
C32—C33—C34—O34 | 180.0 (3) | C73—C74—C77—C78 | −174.9 (3) |
C32—C33—C34—C35 | 0.2 (5) | C74—C77—C78—C79 | −178.0 (3) |
O34—C34—C35—C36 | −179.7 (3) | C77—C78—C79—C84 | −170.6 (3) |
C33—C34—C35—C36 | 0.1 (5) | C86—N81—C82—C83 | −55.6 (3) |
C32—C31—C36—C35 | 0.4 (4) | N81—C82—C83—C84 | 53.4 (4) |
S2—C31—C36—C35 | 178.5 (2) | C78—C79—C84—C83 | −57.1 (4) |
C34—C35—C36—C31 | −0.4 (5) | C78—C79—C84—C85 | 178.5 (3) |
O22—S2—C41—C46 | 160.2 (2) | C82—C83—C84—C79 | −176.5 (3) |
O21—S2—C41—C46 | 32.3 (3) | C82—C83—C84—C85 | −50.7 (4) |
C31—S2—C41—C46 | −82.9 (3) | C79—C84—C85—C86 | 177.6 (3) |
O22—S2—C41—C42 | −20.8 (3) | C83—C84—C85—C86 | 51.3 (4) |
O21—S2—C41—C42 | −148.7 (2) | C82—N81—C86—C85 | 55.6 (4) |
C31—S2—C41—C42 | 96.1 (3) | C84—C85—C86—N81 | −53.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H91···O44 | 0.95 | 1.87 (4) | 2.790 (3) | 162 (3) |
O9—H92···O14 | 0.83 | 1.96 (4) | 2.766 (3) | 163 (4) |
O24—H24···O14i | 0.82 | 1.69 | 2.499 (3) | 167 |
O34—H34···O44ii | 0.82 | 1.82 | 2.629 (3) | 169 |
N51—H51···O9 | 0.90 | 2.47 | 3.148 (3) | 133 |
N61—H61A···O44iii | 0.90 | 1.91 | 2.810 (3) | 175 |
N61—H61B···N71iv | 0.90 | 1.91 | 2.809 (3) | 173 |
N81—H81B···N51 | 0.90 | 1.85 | 2.742 (4) | 172 |
N81—H81A···O21v | 0.90 | 2.32 | 3.148 (3) | 153 |
N81—H81A···O22v | 0.90 | 2.56 | 3.337 (4) | 145 |
C12—H12···O11 | 0.93 | 2.60 | 2.943 (4) | 102 |
C13—H13···O24vi | 0.93 | 2.58 | 3.205 (4) | 125 |
C26—H26···O11 | 0.93 | 2.55 | 2.917 (4) | 104 |
C32—H32···O21 | 0.93 | 2.58 | 2.934 (3) | 103 |
C33—H33···O9ii | 0.93 | 2.49 | 3.397 (4) | 164 |
C56—H56B···O12iii | 0.97 | 2.59 | 3.432 (4) | 146 |
Symmetry codes: (i) −x+1/2, −y, z+1/2; (ii) −x−1/2, −y, z−1/2; (iii) −x, y+1/2, −z+1/2; (iv) x, y, z+1; (v) x+1/2, −y+1/2, −z; (vi) −x+1/2, −y, z−1/2. |
Experimental details
(5) | (6a) | (6b) | (6c) | |
Crystal data | ||||
Chemical formula | 2(C12H10O4S)·C4H4N2 | C12H10O4S·C10H8N2 | C12H10O4S·C12H10N2 | C12H10O4S·C12H12N2 |
Mr | 580.64 | 406.44 | 432.48 | 434.50 |
Crystal system, space group | Monoclinic, P21/a | Monoclinic, P21/n | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 294 | 294 | 294 | 294 |
a, b, c (Å) | 8.3506 (9), 18.0102 (17), 9.6360 (14) | 7.5765 (10), 23.9154 (10), 11.225 (2) | 7.3981 (8), 12.7472 (15), 13.0006 (13) | 7.7599 (9), 12.4866 (16), 12.914 (2) |
α, β, γ (°) | 90, 110.869 (8), 90 | 90, 105.921 (10), 90 | 115.037 (8), 102.398 (10), 94.239 (10) | 114.003 (14), 104.694 (14), 93.690 (13) |
V (Å3) | 1354.1 (3) | 1955.9 (4) | 1065.9 (2) | 1085.7 (3) |
Z | 2 | 4 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.25 | 0.20 | 0.19 | 0.18 |
Crystal size (mm) | 0.42 × 0.35 × 0.25 | 0.42 × 0.22 × 0.18 | 0.42 × 0.28 × 0.24 | 0.42 × 0.42 × 0.32 |
Data collection | ||||
Diffractometer | Enraf-Nonius CAD-4 diffractometer | Enraf-Nonius CAD-4 diffractometer | Enraf-Nonius CAD-4 diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | Gaussian ABSO in NRCVAX (Gabe et al., 1989) | Gaussian ABSO in NRCVAX96 (Gabe et al., 1989) | Gaussian ABSO in NRCVAX (Gabe et al., 1989) | Gaussian ABSO in NRCVAX (Gabe et al., 1989) |
Tmin, Tmax | 0.915, 0.951 | 0.952, 0.971 | 0.949, 0.967 | 0.934, 0.951 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3271, 3102, 2431 | 3774, 3504, 2461 | 3829, 3829, 2948 | 4973, 4973, 3905 |
Rint | 0.008 | 0.011 | 0.000 | 0.000 |
(sin θ/λ)max (Å−1) | 0.648 | 0.597 | 0.599 | 0.648 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.097, 1.04 | 0.039, 0.098, 1.05 | 0.036, 0.100, 0.98 | 0.042, 0.123, 1.07 |
No. of reflections | 3102 | 3504 | 3829 | 4973 |
No. of parameters | 183 | 265 | 330 | 283 |
No. of restraints | 0 | 0 | 41 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.22 | 0.23, −0.25 | 0.21, −0.20 | 0.43, −0.32 |
Absolute structure | ? | ? | ? | ? |
Absolute structure parameter | ? | ? | ? | ? |
(6d) | (7) | |
Crystal data | ||
Chemical formula | C12H10O4S·C13H14N2 | 2(C13H27N2)·2(C12H9O4S)·H2O |
Mr | 448.52 | 939.25 |
Crystal system, space group | Monoclinic, P21/c | Orthorhombic, P212121 |
Temperature (K) | 150 | 294 |
a, b, c (Å) | 10.0292 (10), 15.579 (2), 15.0208 (10) | 12.2739 (10), 19.454 (2), 20.6251 (13) |
α, β, γ (°) | 90, 105.4699 (10), 90 | 90, 90, 90 |
V (Å3) | 2261.9 (4) | 4924.7 (8) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.18 | 0.17 |
Crystal size (mm) | 0.30 × 0.30 × 0.30 | 0.40 × 0.38 × 0.19 |
Data collection | ||
Diffractometer | Enraf-Nonius KappaCCD diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – | Gaussian ABSO in NRCVAX (Gabe et al., 1989) |
Tmin, Tmax | – | 0.943, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10602, 5465, 3828 | 9558, 8866, 5888 |
Rint | 0.031 | 0.019 |
(sin θ/λ)max (Å−1) | 0.708 | 0.599 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.115, 1.04 | 0.042, 0.103, 1.03 |
No. of reflections | 5465 | 8866 |
No. of parameters | 292 | 595 |
No. of restraints | 0 | 2 |
H-atom treatment | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.36 | 0.21, −0.17 |
Absolute structure | ? | Flack (1983) |
Absolute structure parameter | ? | 0.06 (6) |
Computer programs: CAD4 (Enraf-Nonius, 1992), KappaCCD (Enraf-Nonius, 1997), SET4 & CELDIM (Enraf-Nonius, 1992), DENZO (Enraf-Nonius, 1997), DATRD2 in NRCVAX96 (Gabe et al., 1989), SHELXS97 (Sheldrick, 1997a), SHELXS97 (Sheldrick, 1997), NRCVAX96 and SHELXL97 (Sheldrick, 1997b), NRCVAX96 and SHELXL97 (Sheldrick, 1997), NRCVAX96 (Gabe et al., 1989) and SHELXL97 (Sheldrick, 1997b), NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998), NRCVAX96, SHELXL97 and WORDPERFECT macro PRPCIF97 (Ferguson, 1997), NRCVAX96, SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O24i | 0.93 | 2.46 | 3.353 (2) | 161 |
Symmetry code: (i) x+1, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C46—H46···O14i | 0.93 | 2.57 | 3.476 (3) | 164 |
Symmetry code: (i) x−1, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C33—H33···O9i | 0.93 | 2.49 | 3.397 (4) | 164 |
Symmetry code: (i) −x−1/2, −y, z−1/2. |
(5) | |||
O14—C14 | 1.354 (2) | O24—C24 | 1.3548 (18) |
N1—C2 | 1.329 (2) | N1—C6 | 1.323 (2) |
C2—C6i | 1.372 (3) | ||
O11—S1—C11—C12 | 22.0 (2) | O11—S1—C21—C22 | -19.5 (2) |
(6a) | |||
O14—C14 | 1.349 (2) | O24—C24 | 1.351 (3) |
C33—C34 | 1.378 (3) | ||
O12—S1—C11—C16 | 3.4 (2) | O11—S1—C21—C22 | -24.8 (2) |
Interplanar angle (N31,—C32-C36,C44)(N41,C42–C46,C34) | 24.4 (1) | ||
(6b) | |||
O14—C14 | 1.349 (2) | O24—C24 | 1.344 (2) |
C34—C37 | 1.457 (3) | C54—C57 | 1.456 (5) |
C37—C47 | 1.308 (3) | C57—C67 | 1.303 (5) |
C44—C47 | 1.464 (3) | C64—C67 | 1.464 (5) |
O11—S1—C21—C22 | -0.85 (18) | O12—S1—C11—C16 | 10.68 (17) |
C33—C34—C37—C47 | 179.8 (4) | C53—C54—C57—C67 | 174.3 (12) |
C43—C44—C47—C37 | 176.4 (3) | C63—C64—C67—C57 | 169.4 (10) |
(6c) | |||
O14—C14 | 1.3528 (19) | O24—C24 | 1.347 (2) |
C34—C37 | 1.512 (2) | C44—C47 | 1.515 (2) |
C37—C47 | 1.474 (3) | ||
O12—S1—C11—C16 | 4.25 (16) | O11—S1—C21—C22 | -2.71 (17) |
C33—C34—C37—C47 | 101.9 (3) | C43—C44—C47—C37 | -126.6 (2) |
C35—C34—C37—C47 | -79.2 (3) | C45—C44—C47—C37 | 53.9 (3) |
C34—C37—C47—C44 | 179.7 (2) | ||
(6d) | |||
O14—C14 | 1.3426 (19) | O24—C24 | 1.3477 (18) |
C34—C51 | 1.502 (2) | C44—C53 | 1.506 (2) |
C51—C52 | 1.520 (2) | C52—C53 | 1.521 (2) |
O11—S1—C11—C12 | -24.83 (15) | O12—S1—C21—C26 | -12.27 (14) |
C33—C34—C51—C52 | -28.8 (2) | C45—C44—C53—C52 | -23.4 (2) |
C34—C51—C52—C53 | -178.32 (14) | C51—C52—C53—C44 | -173.91 (14) |
(7) | |||
O14—C14 | 1.302 (3) | O34—C34 | 1.334 (3) |
O24—C24 | 1.331 (3) | O44—C44 | 1.313 (3) |
N51—C52 | 1.453 (4) | N71—C72 | 1.472 (4) |
N51—C56 | 1.471 (4) | N71—C76 | 1.474 (4) |
N61—C62 | 1.492 (4) | N81—C82 | 1.477 (4) |
N61—C66 | 1.491 (4) | N81—C86 | 1.476 (4) |
O11—S1—C11—C12 | -25.3 (3) | O21—S2—C31—C32 | -26.8 (3) |
O11—S1—C21—C26 | 17.1 (3) | O21—S2—C41—C46 | 32.3 (3) |
C54—C57—C58—C59 | 179.8 (3) | C74—C77—C78—C79 | -178.0 (3) |
C57—C58—C59—C64 | -178.5 (3) | C77—C78—C79—C84 | -170.6 (3) |
C53—C54—C57—C58 | -173.9 (3) | C73—C74—C77—C78 | -174.9 (3) |
C55—C54—C57—C58 | 62.9 (4) | C75—C74—C77—C78 | -53.1 (4) |
C58—C59—C64—C63 | -59.9 (4) | C78—C79—C84—C83 | -57.1 (4) |
C58—C59—C64—C65 | 176.8 (3) | C78—C79—C84—C85 | 178.5 (3) |
(5) | |||
O14···N1 | 2.792 (2) | O14—H14···N1 | 167 |
O24···O12i | 2.732 (2) | O24—H24···O12i | 174 |
C13···O24ii | 3.353 (2) | C13—H13···O24ii | 161 |
(6a) | |||
O14···N31 | 2.721 (3) | O14—H14···N31 | 167 |
O24···N41iii | 2.731 (3) | O24—H24···N41iii | 176 |
C12···O12iv | 3.376 (3) | C12—H12···O12iv | 165 |
C42···O14ii | 3.487 (3) | C42—H42···O14ii | 167 |
(6b) | |||
O14···N31 | 2.743 (4) | O14—H14···N31 | 171 |
O14···N51v | 2.730 (7) | O14—H14···N51v | 172 |
O24···N41 | 2.688 (5) | O24—H24···N41 | 173 |
O24···N61v | 2.714 (7) | O24—H24···N61v | 174 |
(6c) | |||
O14···N31 | 2.735 (2) | O14—H14···N31 | 170 |
O24···N41v | 2.706 (2) | O24—H24···N41v | 174 |
C46···O14vi | 3.476 (3) | C46—H46···O14vi | 164 |
(6d) | |||
O14···N31 | 2.6514 (19) | O14—H14···N31 | 171 |
O24···N41vii | 2.6850 (18) | O24—H24···N41vii | 166 |
C12···O11viii | 3.428 (2) | C12—H12···O11viii | 160 |
(7) | |||
O9···O44 | 2.790 (3) | O9—H91···O44 | 162 (3) |
O9···O14 | 2.766 (3) | O9—H92···O14 | 163 (4) |
O24···O14ix | 2.499 (3) | O24—H24···O14ix | 167 |
O34···O44x | 2.629 (3) | O24—H24···O44x | 169 |
N51···O9 | 3.148 (3) | N51—H51···O9 | 133 |
N61···N71xi | 2.809 (3) | N61—H61B···N7xi | 173 |
N61···O44xii | 2.810 (3) | N61—H61A···O44xii | 175 |
N81···N51 | 2.742 (4) | N81—H81B···N51 | 172 |
N81···O21xiii | 3.148 (3) | N81—H81A···O21xiii | 153* |
N81···O22xiii | 3.337 (4) | N81—H81A···O22xiii | 145* |
C33···O9 | 3.397 (4) | C33—H33···O9 | 164 |
*Angle O21xiii···H81A···O22xiii is 61°; sum of angles at H81A is 359°. Symmetry codes: (i) x-1,y,z; (ii) 1+x,y,1+z (iii) 3/2-x,1/2+y,3/2-z; (iv) 1/2+x, 1/2-y, 1/2+z; (v) 1+x,1+y,2+z; (vi) x-1,y,z-1 (vii) 2+x,y,z; (viii) -x,-y,-z. (ix) 1/2-x,-y,1/2+z; (x) -1/2-x,-y,z-1/2; (xi) x,y,1+z; (xii) -x,1/2=y,1/2-z; (xiii) 1/2+x,1/2-y,-z. |
None in this version