Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001684/na6043sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001684/na6043Isup2.hkl |
CCDC reference: 159761
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.123
- Data-to-parameter ratio = 17.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 30.50 From the CIF: _reflns_number_total 3392 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4026 Completeness (_total/calc) 84.25% Alert A: < 85% complete (theta max?)
Alert Level C:
PLAT_320 Alert C Check Hybridisation of S(51) in main residue ?
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
A mixture of the Meldrum's acid (6.94 mmol) and trimethyl orthoformate (34.7 mmol) was heated to reflux for 2.5 h, then 2-aminobenzothiazole (6.94 mmol) was added and the mixture was heated for a further 5 min. The title compound precipitated and was separated by filtration and was recrystallized from a dimethylformamide–ethanol mixture, affording crystals suitable for X-ray diffraction (m.p. 480–481 K, yield: 60%).
H atoms were treated as riding with C—H distances in the range 0.95–0.98 Å and an N—H distance of 0.88 Å.
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
Fig. 1. A view of the title molecule with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C14H12N2O4S | Dx = 1.526 Mg m−3 |
Mr = 304.32 | Melting point: 480 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.3459 (13) Å | Cell parameters from 6132 reflections |
b = 19.235 (4) Å | θ = 1.0–30.5° |
c = 11.144 (2) Å | µ = 0.26 mm−1 |
β = 103.07 (3)° | T = 150 K |
V = 1325.0 (5) Å3 | Needle, orange |
Z = 4 | 0.38 × 0.05 × 0.05 mm |
F(000) = 632 |
KappaCCD diffractometer | 3392 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2645 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
ϕ and ω scans with κ offsets | θmax = 30.5°, θmin = 2.1° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −9→8 |
Tmin = 0.908, Tmax = 0.987 | k = −22→27 |
12128 measured reflections | l = −13→15 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0684P)2 + 0.1432P] where P = (Fo2 + 2Fc2)/3 |
3392 reflections | (Δ/σ)max = 0.001 |
192 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
C14H12N2O4S | V = 1325.0 (5) Å3 |
Mr = 304.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.3459 (13) Å | µ = 0.26 mm−1 |
b = 19.235 (4) Å | T = 150 K |
c = 11.144 (2) Å | 0.38 × 0.05 × 0.05 mm |
β = 103.07 (3)° |
KappaCCD diffractometer | 3392 independent reflections |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 2645 reflections with I > 2σ(I) |
Tmin = 0.908, Tmax = 0.987 | Rint = 0.081 |
12128 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.42 e Å−3 |
3392 reflections | Δρmin = −0.52 e Å−3 |
192 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. no transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.30516 (18) | 0.33588 (5) | 1.01481 (10) | 0.0176 (3) | |
C2 | 1.2845 (3) | 0.26447 (8) | 1.05018 (14) | 0.0160 (3) | |
C21 | 1.4987 (3) | 0.22996 (9) | 1.05657 (16) | 0.0214 (4) | |
C22 | 1.2121 (3) | 0.26217 (9) | 1.17025 (14) | 0.0211 (4) | |
O3 | 1.13153 (17) | 0.22842 (6) | 0.95487 (10) | 0.0175 (3) | |
C4 | 0.9419 (3) | 0.25966 (8) | 0.90183 (14) | 0.0164 (3) | |
O41 | 0.80048 (19) | 0.22442 (6) | 0.83965 (11) | 0.0232 (3) | |
C5 | 0.9286 (2) | 0.33450 (8) | 0.92197 (14) | 0.0155 (3) | |
C6 | 1.1201 (2) | 0.37333 (8) | 0.97893 (13) | 0.0149 (3) | |
O61 | 1.12713 (19) | 0.43617 (6) | 0.99149 (10) | 0.0200 (3) | |
C51 | 0.7346 (3) | 0.36591 (8) | 0.87199 (14) | 0.0164 (3) | |
N51 | 0.6866 (2) | 0.43317 (7) | 0.87370 (12) | 0.0166 (3) | |
S51 | 0.41125 (6) | 0.54339 (2) | 0.82927 (4) | 0.01825 (14) | |
C52 | 0.4810 (3) | 0.45697 (8) | 0.81356 (14) | 0.0159 (3) | |
N53 | 0.3390 (2) | 0.41683 (7) | 0.74643 (12) | 0.0178 (3) | |
C54 | 0.1509 (3) | 0.45444 (8) | 0.70129 (15) | 0.0166 (3) | |
C55 | −0.0374 (3) | 0.42851 (9) | 0.62415 (15) | 0.0226 (4) | |
C56 | −0.2110 (3) | 0.47256 (10) | 0.58642 (17) | 0.0259 (4) | |
C57 | −0.2004 (3) | 0.54215 (9) | 0.62270 (17) | 0.0254 (4) | |
C58 | −0.0151 (3) | 0.56924 (9) | 0.69764 (15) | 0.0206 (4) | |
C59 | 0.1594 (3) | 0.52439 (8) | 0.73635 (14) | 0.0164 (3) | |
H21A | 1.4915 | 0.1815 | 1.0824 | 0.032* | |
H21B | 1.6113 | 0.2545 | 1.1163 | 0.032* | |
H21C | 1.5332 | 0.2314 | 0.9752 | 0.032* | |
H22A | 1.0651 | 0.2809 | 1.1577 | 0.032* | |
H22B | 1.3105 | 0.2902 | 1.2321 | 0.032* | |
H22C | 1.2136 | 0.2140 | 1.1989 | 0.032* | |
H51A | 0.6212 | 0.3362 | 0.8314 | 0.020* | |
H51 | 0.7842 | 0.4628 | 0.9126 | 0.020* | |
H55 | −0.0456 | 0.3814 | 0.5982 | 0.027* | |
H56 | −0.3404 | 0.4552 | 0.5347 | 0.031* | |
H57 | −0.3226 | 0.5714 | 0.5954 | 0.030* | |
H58 | −0.0069 | 0.6167 | 0.7219 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0176 (5) | 0.0113 (6) | 0.0220 (6) | −0.0004 (4) | 0.0004 (5) | 0.0039 (4) |
C2 | 0.0187 (8) | 0.0103 (7) | 0.0171 (8) | 0.0001 (6) | 0.0000 (6) | 0.0000 (6) |
C21 | 0.0202 (8) | 0.0186 (8) | 0.0240 (9) | 0.0030 (7) | 0.0017 (7) | 0.0011 (7) |
C22 | 0.0298 (9) | 0.0161 (8) | 0.0171 (8) | 0.0022 (7) | 0.0047 (7) | 0.0017 (6) |
O3 | 0.0193 (6) | 0.0114 (6) | 0.0196 (6) | 0.0014 (4) | −0.0002 (5) | −0.0022 (4) |
C4 | 0.0180 (8) | 0.0146 (8) | 0.0163 (8) | 0.0018 (6) | 0.0035 (6) | 0.0004 (6) |
O41 | 0.0215 (6) | 0.0173 (6) | 0.0278 (6) | −0.0006 (5) | −0.0010 (5) | −0.0078 (5) |
C5 | 0.0183 (8) | 0.0126 (8) | 0.0147 (7) | 0.0005 (6) | 0.0015 (6) | −0.0006 (6) |
C6 | 0.0190 (8) | 0.0135 (8) | 0.0124 (7) | 0.0008 (6) | 0.0038 (6) | 0.0017 (6) |
O61 | 0.0237 (6) | 0.0104 (6) | 0.0242 (6) | −0.0010 (4) | 0.0021 (5) | −0.0006 (4) |
C51 | 0.0184 (7) | 0.0147 (8) | 0.0154 (7) | −0.0001 (6) | 0.0019 (6) | −0.0010 (6) |
N51 | 0.0172 (7) | 0.0129 (7) | 0.0177 (7) | 0.0006 (5) | −0.0001 (5) | −0.0008 (5) |
S51 | 0.0188 (2) | 0.0114 (2) | 0.0221 (2) | 0.00052 (14) | −0.00051 (16) | −0.00246 (14) |
C52 | 0.0202 (8) | 0.0120 (8) | 0.0151 (8) | 0.0004 (6) | 0.0030 (6) | 0.0005 (6) |
N53 | 0.0198 (7) | 0.0138 (7) | 0.0181 (7) | 0.0014 (5) | 0.0004 (5) | −0.0009 (5) |
C54 | 0.0195 (8) | 0.0142 (8) | 0.0156 (8) | 0.0010 (6) | 0.0029 (6) | 0.0019 (6) |
C55 | 0.0254 (9) | 0.0165 (8) | 0.0232 (9) | −0.0009 (7) | −0.0004 (7) | −0.0013 (7) |
C56 | 0.0194 (8) | 0.0270 (9) | 0.0265 (9) | −0.0021 (7) | −0.0046 (7) | 0.0022 (7) |
C57 | 0.0195 (8) | 0.0264 (10) | 0.0276 (9) | 0.0060 (7) | 0.0000 (7) | 0.0060 (7) |
C58 | 0.0236 (8) | 0.0147 (8) | 0.0233 (8) | 0.0037 (7) | 0.0047 (7) | 0.0009 (7) |
C59 | 0.0181 (8) | 0.0154 (8) | 0.0150 (8) | 0.0001 (6) | 0.0026 (6) | −0.0002 (6) |
O1—C6 | 1.3583 (18) | C51—H51A | 0.9500 |
O1—C2 | 1.4430 (18) | N51—C52 | 1.402 (2) |
C2—O3 | 1.4439 (18) | N51—H51 | 0.8800 |
C2—C21 | 1.500 (2) | S51—C59 | 1.7355 (16) |
C2—C22 | 1.511 (2) | S51—C52 | 1.7391 (15) |
C21—H21A | 0.9800 | C52—N53 | 1.290 (2) |
C21—H21B | 0.9800 | N53—C54 | 1.389 (2) |
C21—H21C | 0.9800 | C54—C55 | 1.397 (2) |
C22—H22A | 0.9800 | C54—C59 | 1.399 (2) |
C22—H22B | 0.9800 | C55—C56 | 1.378 (2) |
C22—H22C | 0.9800 | C55—H55 | 0.9500 |
O3—C4 | 1.3555 (18) | C56—C57 | 1.395 (3) |
C4—O41 | 1.2097 (18) | C56—H56 | 0.9500 |
C4—C5 | 1.462 (2) | C57—C58 | 1.381 (2) |
C5—C51 | 1.371 (2) | C57—H57 | 0.9500 |
C5—C6 | 1.445 (2) | C58—C59 | 1.393 (2) |
C6—O61 | 1.2164 (19) | C58—H58 | 0.9500 |
C51—N51 | 1.330 (2) | ||
C6—O1—C2 | 117.34 (12) | N51—C51—C5 | 127.59 (15) |
O1—C2—O3 | 110.10 (11) | N51—C51—H51A | 116.2 |
O1—C2—C21 | 107.27 (13) | C5—C51—H51A | 116.2 |
O3—C2—C21 | 105.88 (12) | C51—N51—C52 | 120.14 (14) |
O1—C2—C22 | 109.54 (12) | C51—N51—H51 | 119.9 |
O3—C2—C22 | 110.41 (13) | C52—N51—H51 | 119.9 |
C21—C2—C22 | 113.52 (14) | C59—S51—C52 | 87.69 (8) |
C2—C21—H21A | 109.5 | N53—C52—N51 | 122.31 (14) |
C2—C21—H21B | 109.5 | N53—C52—S51 | 118.05 (12) |
H21A—C21—H21B | 109.5 | N51—C52—S51 | 119.64 (11) |
C2—C21—H21C | 109.5 | C52—N53—C54 | 109.19 (13) |
H21A—C21—H21C | 109.5 | N53—C54—C55 | 125.62 (14) |
H21B—C21—H21C | 109.5 | N53—C54—C59 | 115.11 (14) |
C2—C22—H22A | 109.5 | C55—C54—C59 | 119.26 (15) |
C2—C22—H22B | 109.5 | C56—C55—C54 | 118.82 (16) |
H22A—C22—H22B | 109.5 | C56—C55—H55 | 120.6 |
C2—C22—H22C | 109.5 | C54—C55—H55 | 120.6 |
H22A—C22—H22C | 109.5 | C55—C56—C57 | 121.22 (16) |
H22B—C22—H22C | 109.5 | C55—C56—H56 | 119.4 |
C4—O3—C2 | 119.39 (12) | C57—C56—H56 | 119.4 |
O41—C4—O3 | 118.15 (14) | C58—C57—C56 | 121.05 (16) |
O41—C4—C5 | 125.35 (14) | C58—C57—H57 | 119.5 |
O3—C4—C5 | 116.47 (13) | C56—C57—H57 | 119.5 |
C51—C5—C6 | 122.64 (14) | C57—C58—C59 | 117.52 (15) |
C51—C5—C4 | 116.67 (14) | C57—C58—H58 | 121.2 |
C6—C5—C4 | 120.27 (14) | C59—C58—H58 | 121.2 |
O61—C6—O1 | 119.10 (14) | C58—C59—C54 | 122.13 (15) |
O61—C6—C5 | 124.69 (14) | C58—C59—S51 | 127.93 (13) |
O1—C6—C5 | 116.13 (13) | C54—C59—S51 | 109.94 (12) |
C6—O1—C2—O3 | 52.11 (17) | C51—N51—C52—N53 | −6.1 (2) |
C6—O1—C2—C21 | 166.88 (13) | C51—N51—C52—S51 | 173.61 (12) |
C6—O1—C2—C22 | −69.48 (16) | C59—S51—C52—N53 | 0.74 (14) |
O1—C2—O3—C4 | −44.54 (17) | C59—S51—C52—N51 | −179.02 (13) |
C21—C2—O3—C4 | −160.19 (13) | N51—C52—N53—C54 | 178.81 (14) |
C22—C2—O3—C4 | 76.54 (16) | S51—C52—N53—C54 | −0.94 (18) |
C2—O3—C4—O41 | −166.52 (13) | C52—N53—C54—C55 | 179.34 (16) |
C2—O3—C4—C5 | 15.38 (19) | C52—N53—C54—C59 | 0.7 (2) |
O41—C4—C5—C51 | 4.2 (2) | N53—C54—C55—C56 | −179.64 (15) |
O3—C4—C5—C51 | −177.86 (13) | C59—C54—C55—C56 | −1.0 (3) |
O41—C4—C5—C6 | −168.60 (15) | C54—C55—C56—C57 | 0.8 (3) |
O3—C4—C5—C6 | 9.3 (2) | C55—C56—C57—C58 | 0.1 (3) |
C2—O1—C6—O61 | 153.43 (13) | C56—C57—C58—C59 | −0.6 (3) |
C2—O1—C6—C5 | −29.61 (18) | C57—C58—C59—C54 | 0.3 (3) |
C51—C5—C6—O61 | 2.3 (2) | C57—C58—C59—S51 | 179.63 (13) |
C4—C5—C6—O61 | 174.68 (15) | N53—C54—C59—C58 | 179.29 (14) |
C51—C5—C6—O1 | −174.44 (13) | C55—C54—C59—C58 | 0.5 (3) |
C4—C5—C6—O1 | −2.1 (2) | N53—C54—C59—S51 | −0.18 (18) |
C6—C5—C51—N51 | −4.4 (3) | C55—C54—C59—S51 | −178.92 (13) |
C4—C5—C51—N51 | −177.04 (15) | C52—S51—C59—C58 | −179.69 (16) |
C5—C51—N51—C52 | 177.55 (15) | C52—S51—C59—C54 | −0.27 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N51—H51···O61i | 0.88 | 2.23 | 3.028 (2) | 151 |
N51—H51···O61 | 0.88 | 2.22 | 2.807 (2) | 124 |
Symmetry code: (i) −x+2, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C14H12N2O4S |
Mr | 304.32 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 6.3459 (13), 19.235 (4), 11.144 (2) |
β (°) | 103.07 (3) |
V (Å3) | 1325.0 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.38 × 0.05 × 0.05 |
Data collection | |
Diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.908, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12128, 3392, 2645 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.714 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.123, 1.08 |
No. of reflections | 3392 |
No. of parameters | 192 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.42, −0.52 |
Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2000), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
C51—N51 | 1.330 (2) | S51—C52 | 1.7391 (15) |
N51—C52 | 1.402 (2) | C52—N53 | 1.290 (2) |
S51—C59 | 1.7355 (16) | N53—C54 | 1.389 (2) |
C51—N51—C52 | 120.14 (14) | C52—N53—C54 | 109.19 (13) |
C59—S51—C52 | 87.69 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N51—H51···O61i | 0.88 | 2.23 | 3.028 (2) | 151 |
N51—H51···O61 | 0.88 | 2.22 | 2.807 (2) | 124 |
Symmetry code: (i) −x+2, −y+1, −z+2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
We have focused on benzothiazole derivatives, which have shown diverse applications, as analgesics (Mehra et al., 1980), anti-inflammatory agents, antineoplasics (Cheng et al., 1993) and antimicrobial agents (Mehra et al., 1980; El-Shaaer et al., 1998), in our search for biological active molecules. Benzothiazole derivatives have been prepared by a known reaction (Quiroga et al., 1998). The title compound, (I), was prepared by condensation of Meldrum's acid, 2,2-dimethyl-1,3-dioxane-4,6-dione), 2-aminobenzothiazole and trimethyl orthoformate.
The supramolecular structure consists of base-paired dimers with an R22(12) motif (Bernstein et al., 1995), formed by the N51—H51···O61i hydrogen bond which is repeated across the centre at (1,1/2,1).
Geometric parameters are given in Table 1 and details of hydrogen bonds are given in Table 2. Fig. 1 shows a view of the molecule.
Examination of the structure with PLATON (Spek, 2000) showed that there were no solvent-accessible voids in the crystal lattice.