Buy article online - an online subscription or single-article purchase is required to access this article.
In the title compound, C
13H
14N
2O
2S, intermolecular N—H
O(N) hydrogen bonds link the molecules in the crystal structure into sheets parallel to the
bc plane.
Supporting information
CCDC reference: 277249
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.106
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.92 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C11 .. 5.01 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Version 3.60; Rigaku/MSC,2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).
Methyl 2-amino-4-methyl-6-phenyl-6
H-1,3-thiazine-5-carboxylate
top
Crystal data top
C13H14N2O2S | F(000) = 552.00 |
Mr = 262.33 | Dx = 1.322 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 7566 reflections |
a = 11.3798 (4) Å | θ = 3.0–27.4° |
b = 8.7584 (3) Å | µ = 0.24 mm−1 |
c = 13.3900 (6) Å | T = 295 K |
β = 99.178 (1)° | Block, colorless |
V = 1317.48 (9) Å3 | 0.32 × 0.30 × 0.27 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2078 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.031 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR: Higashi, 1995) | h = −14→14 |
Tmin = 0.911, Tmax = 0.937 | k = −11→11 |
12745 measured reflections | l = −17→17 |
3005 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[0.0011Fo2 + σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.039 | (Δ/σ)max < 0.001 |
wR(F2) = 0.106 | Δρmax = 0.34 e Å−3 |
S = 1.01 | Δρmin = −0.31 e Å−3 |
2884 reflections | Extinction correction: Larson (1970), equation 22 |
164 parameters | Extinction coefficient: 70 (21) |
H-atom parameters constrained | |
Special details top
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.79014 (4) | 0.29130 (5) | 0.60115 (3) | 0.0477 (1) | |
O1 | 0.8568 (1) | 0.5982 (1) | 0.29221 (9) | 0.0571 (4) | |
O2 | 0.7572 (1) | 0.6759 (1) | 0.41244 (9) | 0.0600 (4) | |
N1 | 0.9257 (1) | 0.1849 (1) | 0.4672 (1) | 0.0416 (4) | |
N2 | 0.9003 (1) | 0.0282 (2) | 0.5978 (1) | 0.0519 (4) | |
C1 | 0.7269 (1) | 0.3846 (2) | 0.4825 (1) | 0.0432 (4) | |
C2 | 0.8253 (1) | 0.4241 (2) | 0.4229 (1) | 0.0397 (4) | |
C3 | 0.9156 (1) | 0.3244 (2) | 0.4177 (1) | 0.0386 (4) | |
C4 | 0.8788 (1) | 0.1594 (2) | 0.5484 (1) | 0.0409 (4) | |
C5 | 0.6269 (1) | 0.2892 (2) | 0.4255 (1) | 0.0465 (5) | |
C6 | 0.5206 (2) | 0.2743 (4) | 0.4630 (2) | 0.0896 (9) | |
C7 | 0.4298 (2) | 0.1840 (4) | 0.4152 (2) | 0.113 (1) | |
C8 | 0.4425 (2) | 0.1058 (3) | 0.3285 (2) | 0.0872 (8) | |
C9 | 0.5444 (2) | 0.1238 (3) | 0.2889 (2) | 0.0717 (7) | |
C10 | 0.6360 (2) | 0.2160 (2) | 0.3369 (1) | 0.0557 (5) | |
C11 | 0.8174 (1) | 0.5702 (2) | 0.3684 (1) | 0.0419 (4) | |
C12 | 0.7492 (2) | 0.8249 (2) | 0.3666 (2) | 0.0760 (7) | |
C13 | 1.0157 (1) | 0.3486 (2) | 0.3588 (1) | 0.0471 (5) | |
H1 | 0.6918 | 0.4811 | 0.5002 | 0.053* | |
H6 | 0.5097 | 0.3291 | 0.5247 | 0.110* | |
H7 | 0.3556 | 0.1738 | 0.4431 | 0.137* | |
H8 | 0.3791 | 0.0385 | 0.2957 | 0.102* | |
H9 | 0.5536 | 0.0717 | 0.2259 | 0.085* | |
H10 | 0.7085 | 0.2284 | 0.3069 | 0.067* | |
H121 | 0.6926 | 0.8222 | 0.3053 | 0.093* | |
H122 | 0.7238 | 0.8976 | 0.4124 | 0.092* | |
H123 | 0.8257 | 0.8543 | 0.3515 | 0.093* | |
H131 | 1.0255 | 0.4559 | 0.3481 | 0.058* | |
H133 | 1.0879 | 0.3076 | 0.3960 | 0.057* | |
H132 | 0.9977 | 0.2977 | 0.2947 | 0.058* | |
H201 | 0.8703 | 0.0084 | 0.6560 | 0.064* | |
H202 | 0.9554 | −0.0316 | 0.5760 | 0.064* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0607 (3) | 0.0508 (3) | 0.0350 (2) | 0.0046 (2) | 0.0176 (2) | 0.0005 (2) |
O1 | 0.0798 (9) | 0.0499 (7) | 0.0471 (7) | 0.0097 (6) | 0.0267 (7) | 0.0113 (6) |
O2 | 0.0920 (9) | 0.0398 (7) | 0.0526 (7) | 0.0181 (6) | 0.0253 (7) | 0.0041 (5) |
N1 | 0.0481 (7) | 0.0410 (7) | 0.0381 (7) | 0.0056 (6) | 0.0146 (6) | 0.0051 (6) |
N2 | 0.0673 (9) | 0.0499 (9) | 0.0428 (8) | 0.0103 (7) | 0.0222 (7) | 0.0132 (7) |
C1 | 0.0512 (9) | 0.0388 (8) | 0.0435 (9) | 0.0085 (7) | 0.0195 (7) | 0.0024 (7) |
C2 | 0.0483 (9) | 0.0375 (8) | 0.0349 (8) | 0.0017 (7) | 0.0118 (7) | 0.0010 (7) |
C3 | 0.0453 (8) | 0.0389 (8) | 0.0329 (8) | −0.0004 (7) | 0.0098 (7) | 0.0002 (6) |
C4 | 0.0440 (8) | 0.0439 (9) | 0.0355 (8) | 0.0001 (7) | 0.0089 (7) | 0.0010 (7) |
C5 | 0.0439 (9) | 0.051 (1) | 0.0463 (9) | 0.0072 (7) | 0.0121 (7) | 0.0083 (8) |
C6 | 0.063 (1) | 0.141 (2) | 0.071 (1) | −0.018 (1) | 0.029 (1) | −0.020 (2) |
C7 | 0.060 (1) | 0.186 (3) | 0.096 (2) | −0.039 (2) | 0.025 (1) | −0.012 (2) |
C8 | 0.062 (1) | 0.116 (2) | 0.078 (2) | −0.023 (1) | −0.007 (1) | 0.007 (2) |
C9 | 0.064 (1) | 0.084 (2) | 0.062 (1) | −0.000 (1) | −0.004 (1) | −0.007 (1) |
C10 | 0.050 (1) | 0.066 (1) | 0.051 (1) | 0.0017 (9) | 0.0101 (8) | −0.0026 (9) |
C11 | 0.0482 (9) | 0.0396 (9) | 0.0377 (8) | 0.0026 (7) | 0.0067 (7) | −0.0029 (7) |
C12 | 0.120 (2) | 0.041 (1) | 0.069 (1) | 0.021 (1) | 0.022 (1) | 0.008 (1) |
C13 | 0.0470 (9) | 0.051 (1) | 0.0461 (9) | 0.0034 (8) | 0.0162 (8) | 0.0081 (8) |
Geometric parameters (Å, º) top
S1—C1 | 1.829 (2) | C8—C9 | 1.359 (3) |
S1—C4 | 1.755 (2) | C9—C10 | 1.392 (3) |
O1—C11 | 1.204 (2) | N2—H201 | 0.9161 |
O2—C11 | 1.343 (2) | N2—H202 | 0.9000 |
O2—C12 | 1.439 (2) | C1—H1 | 0.9800 |
N1—C3 | 1.386 (2) | C6—H6 | 0.9800 |
N1—C4 | 1.306 (2) | C7—H7 | 0.9800 |
N2—C4 | 1.328 (2) | C8—H8 | 0.9800 |
C1—C2 | 1.516 (2) | C9—H9 | 0.9800 |
C1—C5 | 1.517 (2) | C10—H10 | 0.9800 |
C2—C3 | 1.359 (2) | C12—H121 | 0.9600 |
C2—C11 | 1.468 (2) | C12—H122 | 0.9600 |
C3—C13 | 1.500 (2) | C12—H123 | 0.9600 |
C5—C6 | 1.388 (3) | C13—H131 | 0.9600 |
C5—C10 | 1.367 (3) | C13—H133 | 0.9600 |
C6—C7 | 1.376 (4) | C13—H132 | 0.9600 |
C7—C8 | 1.375 (4) | | |
| | | |
S1—C1—C2 | 109.8 (1) | O2—C12—H121 | 109.3132 |
C4—S1—C1 | 96.73 (8) | O2—C12—H122 | 109.4997 |
S1—C1—C5 | 110.6 (1) | O2—C12—H123 | 109.6289 |
S1—C4—N1 | 124.1 (1) | H201—N2—C4 | 121.5479 |
S1—C4—N2 | 116.2 (1) | H202—N2—C4 | 115.1242 |
O1—C11—C2 | 126.7 (2) | H202—N2—H201 | 122.5504 |
O1—C11—O2 | 121.1 (1) | H1—C1—C2 | 107.1010 |
O2—C11—C2 | 112.2 (1) | H1—C1—C5 | 107.1588 |
C12—O2—C11 | 116.1 (2) | C3—C13—H131 | 109.4743 |
N1—C3—C2 | 123.2 (1) | C3—C13—H132 | 109.3948 |
C4—N1—C3 | 122.4 (1) | C3—C13—H133 | 109.5326 |
N1—C3—C13 | 111.3 (1) | C5—C6—H6 | 119.6151 |
N1—C4—N2 | 119.7 (2) | C5—C10—H10 | 119.2965 |
C1—C2—C3 | 120.6 (1) | H6—C6—C7 | 119.1750 |
C5—C1—C2 | 114.7 (1) | C6—C7—H7 | 120.1767 |
C1—C2—C11 | 118.0 (1) | H7—C7—C8 | 119.3642 |
C1—C5—C6 | 119.8 (2) | C7—C8—H8 | 120.5738 |
C1—C5—C10 | 122.7 (2) | C8—C9—H9 | 119.8146 |
C11—C2—C3 | 121.4 (1) | H8—C8—C9 | 120.5340 |
C2—C3—C13 | 125.5 (1) | C9—C10—H10 | 119.5147 |
C10—C5—C6 | 117.5 (2) | H9—C9—C10 | 119.5337 |
C5—C6—C7 | 121.2 (2) | H122—C12—H121 | 109.4737 |
C5—C10—C9 | 121.2 (2) | H123—C12—H121 | 109.5392 |
C6—C7—C8 | 120.5 (3) | H123—C12—H122 | 109.3726 |
C7—C8—C9 | 118.9 (2) | H132—C13—H131 | 109.4659 |
C8—C9—C10 | 120.7 (2) | H133—C13—H131 | 109.4732 |
S1—C1—H1 | 107.1536 | H132—C13—H133 | 109.4864 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H201···O1i | 0.92 | 2.08 | 2.9425 (18) | 157 |
N2—H202···N1ii | 0.90 | 2.05 | 2.9515 (18) | 175 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.