Buy article online - an online subscription or single-article purchase is required to access this article.
The structure of the title compound, C
11H
11NOS, has been reported previously at room temperature by Ferguson & Ruhl [
Cryst. Struct. Commun. (1982),
11, 1033–1038]. We report here a redetermination, at 100 (2) K, with improved precision. The structure displays N—H
O hydrogen bonding.
Supporting information
CCDC reference: 604957
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C)= 0.003 Å
- R factor = 0.052
- wR factor = 0.120
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury1.4 (Bruno et al.,
2002;
Taylor & Macrae, 2001); software used to prepare material for publication: SHELXTL (Bruker, 1999).
2-Acetyl-3-methyl-4
H-1,4-benzothiazine
top
Crystal data top
C11H11NOS | F(000) = 432 |
Mr = 205.27 | Dx = 1.435 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2288 reflections |
a = 7.3606 (15) Å | θ = 2.4–27.5° |
b = 7.4968 (15) Å | µ = 0.30 mm−1 |
c = 17.375 (4) Å | T = 100 K |
β = 97.78 (3)° | Prism, orange |
V = 949.9 (4) Å3 | 0.4 × 0.2 × 0.2 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2085 independent reflections |
Radiation source: fine-focus sealed tube | 1908 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 8.192 pixels mm-1 | θmax = 27.5°, θmin = 2.4° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −9→9 |
Tmin = 0.845, Tmax = 0.941 | l = −21→22 |
6163 measured reflections | |
Refinement top
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.4415P] where P = (Fo2 + 2Fc2)/3 |
2085 reflections | (Δ/σ)max < 0.001 |
132 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.43497 (7) | 0.82108 (7) | 0.11543 (3) | 0.01251 (17) | |
O1 | 0.1552 (2) | 0.7244 (2) | 0.01159 (9) | 0.0166 (4) | |
N1 | 0.7922 (3) | 0.8104 (2) | 0.03928 (11) | 0.0134 (4) | |
C1 | 0.8055 (3) | 0.8879 (3) | 0.11375 (11) | 0.0108 (4) | |
C2 | 0.9740 (3) | 0.9576 (3) | 0.14694 (12) | 0.0130 (4) | |
H2 | 1.0764 | 0.9522 | 0.1191 | 0.016* | |
C3 | 0.9932 (3) | 1.0345 (3) | 0.22019 (13) | 0.0149 (4) | |
H3 | 1.1088 | 1.0799 | 0.2427 | 0.018* | |
C4 | 0.8430 (3) | 1.0453 (3) | 0.26065 (12) | 0.0143 (4) | |
H4 | 0.8556 | 1.0970 | 0.3110 | 0.017* | |
C5 | 0.6744 (3) | 0.9800 (3) | 0.22688 (12) | 0.0129 (4) | |
H5 | 0.5713 | 0.9890 | 0.2542 | 0.015* | |
C6 | 0.6541 (3) | 0.9015 (3) | 0.15360 (12) | 0.0108 (4) | |
C7 | 0.4671 (3) | 0.7596 (3) | 0.01813 (11) | 0.0102 (4) | |
C8 | 0.6376 (3) | 0.7567 (3) | −0.00609 (12) | 0.0111 (4) | |
C9 | 0.6742 (3) | 0.6947 (3) | −0.08480 (12) | 0.0146 (4) | |
H9A | 0.8059 | 0.7021 | −0.0879 | 0.022* | |
H9B | 0.6072 | 0.7707 | −0.1249 | 0.022* | |
H9C | 0.6332 | 0.5710 | −0.0929 | 0.022* | |
C10 | 0.2922 (3) | 0.7086 (3) | −0.02324 (12) | 0.0117 (4) | |
C11 | 0.2630 (3) | 0.6317 (3) | −0.10406 (12) | 0.0150 (4) | |
H11A | 0.1333 | 0.6011 | −0.1181 | 0.023* | |
H11B | 0.3380 | 0.5241 | −0.1058 | 0.023* | |
H11C | 0.2987 | 0.7199 | −0.1409 | 0.023* | |
H1 | 0.895 (4) | 0.798 (4) | 0.0253 (16) | 0.018* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0076 (3) | 0.0171 (3) | 0.0136 (3) | −0.00184 (19) | 0.00453 (18) | −0.0036 (2) |
O1 | 0.0075 (7) | 0.0229 (8) | 0.0200 (8) | −0.0006 (6) | 0.0043 (6) | −0.0024 (6) |
N1 | 0.0069 (9) | 0.0173 (9) | 0.0169 (9) | 0.0002 (7) | 0.0050 (7) | −0.0020 (7) |
C1 | 0.0076 (9) | 0.0146 (10) | 0.0099 (9) | 0.0013 (8) | 0.0000 (7) | 0.0018 (8) |
C2 | 0.0080 (9) | 0.0147 (10) | 0.0164 (10) | −0.0009 (8) | 0.0025 (8) | 0.0020 (8) |
C3 | 0.0101 (10) | 0.0173 (11) | 0.0163 (10) | −0.0001 (8) | −0.0022 (8) | 0.0000 (8) |
C4 | 0.0144 (10) | 0.0156 (10) | 0.0128 (10) | 0.0008 (8) | 0.0013 (8) | 0.0004 (8) |
C5 | 0.0119 (10) | 0.0143 (10) | 0.0132 (10) | 0.0003 (8) | 0.0042 (8) | 0.0014 (8) |
C6 | 0.0093 (9) | 0.0099 (9) | 0.0136 (10) | −0.0001 (7) | 0.0026 (8) | 0.0012 (8) |
C7 | 0.0093 (10) | 0.0118 (9) | 0.0099 (9) | 0.0005 (8) | 0.0024 (7) | 0.0001 (8) |
C8 | 0.0098 (10) | 0.0086 (9) | 0.0158 (10) | −0.0004 (7) | 0.0046 (8) | 0.0008 (8) |
C9 | 0.0126 (10) | 0.0175 (11) | 0.0148 (10) | −0.0012 (8) | 0.0059 (8) | −0.0018 (8) |
C10 | 0.0100 (10) | 0.0098 (9) | 0.0156 (10) | 0.0012 (7) | 0.0022 (8) | 0.0022 (8) |
C11 | 0.0123 (10) | 0.0167 (10) | 0.0155 (10) | 0.0009 (8) | 0.0000 (8) | −0.0018 (8) |
Geometric parameters (Å, º) top
S1—C6 | 1.765 (2) | C4—H4 | 0.9500 |
S1—C7 | 1.799 (2) | C5—C6 | 1.392 (3) |
O1—C10 | 1.250 (3) | C5—H5 | 0.9500 |
N1—C8 | 1.355 (3) | C7—C8 | 1.377 (3) |
N1—C1 | 1.410 (3) | C7—C10 | 1.439 (3) |
N1—H1 | 0.83 (3) | C8—C9 | 1.503 (3) |
C1—C6 | 1.393 (3) | C9—H9A | 0.9800 |
C1—C2 | 1.396 (3) | C9—H9B | 0.9800 |
C2—C3 | 1.387 (3) | C9—H9C | 0.9800 |
C2—H2 | 0.9500 | C10—C11 | 1.506 (3) |
C3—C4 | 1.391 (3) | C11—H11A | 0.9800 |
C3—H3 | 0.9500 | C11—H11B | 0.9800 |
C4—C5 | 1.388 (3) | C11—H11C | 0.9800 |
| | | |
C6—S1—C7 | 102.17 (10) | C8—C7—C10 | 129.37 (19) |
C8—N1—C1 | 127.22 (19) | C8—C7—S1 | 122.20 (17) |
C8—N1—H1 | 121.5 (19) | C10—C7—S1 | 108.35 (15) |
C1—N1—H1 | 111.3 (19) | N1—C8—C7 | 123.1 (2) |
C6—C1—C2 | 119.52 (19) | N1—C8—C9 | 112.44 (19) |
C6—C1—N1 | 121.72 (19) | C7—C8—C9 | 124.5 (2) |
C2—C1—N1 | 118.73 (19) | C8—C9—H9A | 109.5 |
C3—C2—C1 | 120.61 (19) | C8—C9—H9B | 109.5 |
C3—C2—H2 | 119.7 | H9A—C9—H9B | 109.5 |
C1—C2—H2 | 119.7 | C8—C9—H9C | 109.5 |
C2—C3—C4 | 119.9 (2) | H9A—C9—H9C | 109.5 |
C2—C3—H3 | 120.0 | H9B—C9—H9C | 109.5 |
C4—C3—H3 | 120.0 | O1—C10—C7 | 117.32 (19) |
C5—C4—C3 | 119.5 (2) | O1—C10—C11 | 117.73 (19) |
C5—C4—H4 | 120.3 | C7—C10—C11 | 124.91 (19) |
C3—C4—H4 | 120.3 | C10—C11—H11A | 109.5 |
C4—C5—C6 | 121.0 (2) | C10—C11—H11B | 109.5 |
C4—C5—H5 | 119.5 | H11A—C11—H11B | 109.5 |
C6—C5—H5 | 119.5 | C10—C11—H11C | 109.5 |
C5—C6—C1 | 119.44 (19) | H11A—C11—H11C | 109.5 |
C5—C6—S1 | 117.87 (16) | H11B—C11—H11C | 109.5 |
C1—C6—S1 | 122.69 (16) | | |
| | | |
C8—N1—C1—C6 | 6.9 (3) | C7—S1—C6—C1 | −7.4 (2) |
C8—N1—C1—C2 | −171.1 (2) | C6—S1—C7—C8 | 9.2 (2) |
C6—C1—C2—C3 | 2.2 (3) | C6—S1—C7—C10 | −173.90 (14) |
N1—C1—C2—C3 | −179.81 (19) | C1—N1—C8—C7 | −4.9 (3) |
C1—C2—C3—C4 | −1.0 (3) | C1—N1—C8—C9 | 175.0 (2) |
C2—C3—C4—C5 | −0.5 (3) | C10—C7—C8—N1 | 179.5 (2) |
C3—C4—C5—C6 | 1.0 (3) | S1—C7—C8—N1 | −4.4 (3) |
C4—C5—C6—C1 | 0.2 (3) | C10—C7—C8—C9 | −0.5 (4) |
C4—C5—C6—S1 | 179.66 (16) | S1—C7—C8—C9 | 175.69 (16) |
C2—C1—C6—C5 | −1.8 (3) | C8—C7—C10—O1 | −179.7 (2) |
N1—C1—C6—C5 | −179.70 (19) | S1—C7—C10—O1 | 3.8 (2) |
C2—C1—C6—S1 | 178.81 (16) | C8—C7—C10—C11 | 2.7 (4) |
N1—C1—C6—S1 | 0.9 (3) | S1—C7—C10—C11 | −173.90 (17) |
C7—S1—C6—C5 | 173.12 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.826 (15) | 2.042 (17) | 2.854 (2) | 166.99 (16) |
Symmetry code: (i) x+1, y, z. |
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.