Literature DB >> 23476201

1-(10H-phenothia-zin-10-yl)ethanone.

Eri Tokunaga1, Tsunehisa Okuno.   

Abstract

In the title compound, C14H11NOS, the phenothia-zine unit has a butterfly conformation and the central six-membered ring has a boat form. The fold angle between the benzene rings is 46.39 (7)°, which is larger than found in similar compounds, probably as a result of steric repulsion between the phenothia-zine fragment and the acetyl group.

Entities:  

Year:  2012        PMID： 23476201      PMCID： PMC3588965          DOI： 10.1107/S1600536812045904

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the structures of related N-alkyl­phenothia­zine derivatives, see: Chu & Van der Helm (1974 ▶, 1975 ▶) and of related N-acetyl­phenothia­zine derivatives, see: Meester & Chu (1986 ▶); Wang et al. (2009 ▶); Siddegowda et al. (2011 ▶).

Experimental

Crystal data

C14H11NOS M = 241.31 Monoclinic, a = 21.435 (6) Å b = 8.897 (3) Å c = 12.738 (4) Å β = 111.753 (3)° V = 2256.2 (11) Å3 Z = 8 Mo Kα radiation μ = 0.27 mm−1 T = 93 K 0.17 × 0.10 × 0.10 mm

Data collection

Rigaku Saturn724+ diffractometer Absorption correction: numerical (NUMABS; Rigaku, 1999 ▶) T min = 0.969, T max = 0.974 9030 measured reflections 2584 independent reflections 2337 reflections with F 2 > 2σ(F 2) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.081 S = 1.03 2584 reflections 154 parameters H-atom parameters constrained Δρmax = 0.31 e Å−3 Δρmin = −0.24 e Å−3 Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2010 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812045904/fy2074sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045904/fy2074Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812045904/fy2074Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H11NOSF(000) = 1008.00
Mr = 241.31Dx = 1.421 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2ycCell parameters from 3415 reflections
a = 21.435 (6) Åθ = 2.1–31.1°
b = 8.897 (3) ŵ = 0.27 mm−1
c = 12.738 (4) ÅT = 93 K
β = 111.753 (3)°Block, colorless
V = 2256.2 (11) Å30.17 × 0.10 × 0.10 mm
Z = 8
Rigaku Saturn724+ diffractometer2337 reflections with F2 > 2σ(F2)
Detector resolution: 7.111 pixels mm-1Rint = 0.025
ω scansθmax = 27.5°
Absorption correction: numerical (NUMABS; Rigaku, 1999)h = −27→27
Tmin = 0.969, Tmax = 0.974k = −11→8
9030 measured reflectionsl = −16→16
2584 independent reflections
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.042P)2 + 2.3718P] where P = (Fo2 + 2Fc2)/3
2584 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods
Refinement. Refinement was performed 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).
xyzUiso*/Ueq
S10.414831 (16)0.27277 (3)0.08674 (2)0.01289 (10)
O10.39200 (5)−0.21234 (10)0.18741 (8)0.0181 (2)
N10.37281 (5)0.03491 (12)0.20689 (9)0.0120 (3)
C10.32864 (6)0.04797 (14)0.09052 (10)0.0118 (3)
C20.27278 (7)−0.04399 (14)0.04325 (11)0.0149 (3)
C30.23329 (7)−0.02967 (15)−0.07063 (11)0.0169 (3)
C40.24838 (7)0.07854 (15)−0.13668 (11)0.0163 (3)
C50.30261 (7)0.17472 (15)−0.08875 (11)0.0147 (3)
C60.34325 (6)0.15792 (14)0.02484 (10)0.0121 (3)
C70.41033 (6)0.29392 (14)0.22130 (10)0.0113 (3)
C80.42569 (6)0.43164 (14)0.27746 (11)0.0134 (3)
C90.42106 (6)0.44609 (15)0.38294 (11)0.0156 (3)
C100.39899 (7)0.32640 (15)0.43056 (11)0.0165 (3)
C110.38202 (7)0.19044 (15)0.37316 (11)0.0147 (3)
C120.38932 (6)0.17307 (14)0.26952 (10)0.0116 (3)
C130.40672 (6)−0.09848 (14)0.24523 (11)0.0132 (3)
C140.46316 (7)−0.09615 (15)0.35876 (11)0.0164 (3)
H20.2617−0.11610.08850.0179*
H30.1957−0.0941−0.10380.0202*
H40.22150.0866−0.21480.0195*
H50.31190.2512−0.13300.0177*
H80.43920.51460.24390.0161*
H90.43300.53840.42290.0187*
H100.39550.33760.50240.0198*
H110.36550.10980.40440.0176*
H14A0.4889−0.00300.36680.0197*
H14B0.4927−0.18260.36510.0197*
H14C0.4447−0.10130.41850.0197*
U11U22U33U12U13U23
S10.01464 (17)0.01445 (17)0.01035 (15)−0.00323 (11)0.00552 (12)−0.00079 (11)
O10.0196 (5)0.0115 (5)0.0205 (5)−0.0003 (4)0.0043 (4)−0.0018 (4)
N10.0141 (6)0.0110 (5)0.0098 (5)−0.0003 (4)0.0031 (5)0.0002 (4)
C10.0123 (6)0.0116 (6)0.0110 (6)0.0020 (5)0.0038 (5)−0.0008 (5)
C20.0141 (6)0.0130 (6)0.0176 (7)−0.0003 (5)0.0060 (5)−0.0007 (5)
C30.0119 (7)0.0161 (6)0.0197 (7)0.0003 (5)0.0025 (6)−0.0040 (5)
C40.0129 (6)0.0198 (7)0.0129 (6)0.0048 (5)0.0010 (5)−0.0031 (5)
C50.0164 (7)0.0147 (6)0.0133 (6)0.0035 (5)0.0059 (5)0.0009 (5)
C60.0113 (6)0.0116 (6)0.0132 (6)0.0005 (5)0.0045 (5)−0.0022 (5)
C70.0098 (6)0.0136 (6)0.0101 (6)0.0019 (5)0.0034 (5)−0.0005 (5)
C80.0108 (6)0.0128 (6)0.0157 (6)0.0001 (5)0.0039 (5)−0.0003 (5)
C90.0135 (7)0.0155 (6)0.0156 (6)0.0013 (5)0.0027 (5)−0.0052 (5)
C100.0163 (7)0.0209 (7)0.0122 (6)0.0033 (6)0.0052 (5)−0.0019 (5)
C110.0143 (6)0.0174 (7)0.0131 (6)0.0007 (5)0.0058 (5)0.0021 (5)
C120.0103 (6)0.0116 (6)0.0116 (6)0.0008 (5)0.0026 (5)−0.0008 (5)
C130.0138 (6)0.0128 (6)0.0146 (6)−0.0008 (5)0.0070 (5)0.0022 (5)
C140.0171 (7)0.0163 (6)0.0150 (7)0.0014 (5)0.0050 (6)0.0020 (5)
S1—C61.7673 (13)C9—C101.392 (2)
S1—C71.7621 (15)C10—C111.3903 (19)
O1—C131.2231 (16)C11—C121.394 (3)
N1—C11.4376 (15)C13—C141.5028 (17)
N1—C121.4365 (17)C2—H20.950
N1—C131.3828 (16)C3—H30.950
C1—C21.3897 (18)C4—H40.950
C1—C61.396 (2)C5—H50.950
C2—C31.3881 (18)C8—H80.950
C3—C41.393 (3)C9—H90.950
C4—C51.3893 (19)C10—H100.950
C5—C61.3930 (17)C11—H110.950
C7—C81.3953 (18)C14—H14A0.980
C7—C121.393 (2)C14—H14B0.980
C8—C91.389 (3)C14—H14C0.980
S1···N12.9418 (14)C11···H14Bxiii3.4202
O1···C12.7367 (16)C12···H4v3.0777
O1···C22.9441 (16)C13···H3ii3.5525
O1···C123.5917 (18)C13···H5vii3.2746
C1···C42.7782 (18)C13···H8iii3.5131
C1···C72.9099 (17)C13···H14Ai3.1820
C1···C113.581 (2)C13···H14Bi3.0711
C2···C52.796 (3)C14···H5vii3.5612
C2···C123.5972 (18)C14···H9iii3.4709
C2···C133.1019 (17)C14···H10xiii3.5985
C3···C62.7741 (19)C14···H14Ai3.4899
C6···C122.903 (2)C14···H14Axiii3.3758
C6···C133.4792 (19)C14···H14Bi3.4086
C7···C102.780 (3)C14···H14Cxiii3.2995
C7···C133.508 (2)H2···C2ii3.4044
C8···C112.795 (2)H2···C3ii3.1645
C9···C122.7789 (19)H2···C10ix3.4004
C11···C133.191 (2)H2···H2ii3.1902
C11···C143.130 (3)H2···H3ii2.7183
C12···C142.8638 (19)H2···H4vii2.9472
S1···C8i3.5062 (15)H2···H5vii3.5148
O1···C3ii3.4254 (18)H2···H10ix3.1583
O1···C8iii3.3551 (17)H3···O1ii2.4806
O1···C10iv3.481 (2)H3···C2ii3.3218
O1···C14i3.522 (3)H3···C7v3.4668
C3···O1ii3.4254 (18)H3···C8v3.0805
C3···C8v3.5581 (18)H3···C10ix3.5790
C4···C7v3.362 (2)H3···C13ii3.5525
C4···C8v3.491 (2)H3···H2ii2.7183
C4···C12v3.5717 (19)H3···H5xiv3.5725
C7···C4v3.362 (2)H3···H8v2.8676
C8···S1i3.5062 (15)H3···H10ix2.7814
C8···O1vi3.3551 (17)H4···C7v2.9911
C8···C3v3.5581 (18)H4···C8v2.9579
C8···C4v3.491 (2)H4···C9v3.0259
C8···C8i3.506 (3)H4···C10v3.0919
C10···O1vii3.481 (2)H4···C11v3.0998
C12···C4v3.5717 (19)H4···C12v3.0777
C13···C14i3.503 (3)H4···H2iv2.9472
C14···O1i3.522 (3)H4···H5xiv3.4855
C14···C13i3.503 (3)H4···H8v3.4440
S1···H52.8571H4···H9v3.5674
S1···H82.8527H4···H11iv3.3789
O1···H22.7411H5···O1iv3.3489
O1···H14A3.0798H5···C2v3.5950
O1···H14B2.4958H5···C9viii3.5246
O1···H14C2.9067H5···C13iv3.2746
N1···H22.6627H5···C14iv3.5612
N1···H112.6624H5···H2iv3.5148
N1···H14A2.5881H5···H3xv3.5725
N1···H14B3.2510H5···H4xv3.4855
N1···H14C2.8334H5···H9viii3.0641
C1···H33.2575H5···H11iv3.3848
C1···H53.2778H5···H14Civ2.9882
C2···H43.2687H8···O1vi2.6273
C3···H53.2715H8···C3v3.5369
C4···H23.2716H8···C8i3.0975
C5···H33.2680H8···C13vi3.5131
C6···H23.2727H8···H3v2.8676
C6···H43.2601H8···H4v3.4440
C7···H93.2612H8···H8i2.5542
C7···H113.2720H8···H10viii3.1524
C7···H14A3.3070H8···H14Bvi3.1051
C8···H103.2705H8···H14Bxvi3.5810
C9···H113.2690H9···S1x2.8168
C10···H83.2734H9···O1vi3.5684
C11···H93.2663H9···C9xi3.1910
C11···H14A2.8911H9···C10xi3.5933
C11···H14C2.8813H9···C14vi3.4709
C12···H83.2774H9···H4v3.5674
C12···H103.2657H9···H5x3.0641
C12···H14A2.5664H9···H9xi2.8955
C12···H14C3.0495H9···H14Bvi3.0059
C13···H23.0122H9···H14Cvi3.2172
C13···H113.1065H10···O1vii2.6337
C14···H112.9960H10···C2xii3.5929
H2···H32.3388H10···C3xii3.3992
H3···H42.3384H10···C14xiii3.5985
H4···H52.3425H10···H2xii3.1583
H8···H92.3410H10···H3xii2.7814
H9···H102.3377H10···H8x3.1524
H10···H112.3422H10···H14Bxiii2.7382
H11···H14A3.0286H11···O1vii3.5544
H11···H14C2.4928H11···C1vii3.0992
S1···H9viii2.8168H11···C2vii3.1669
S1···H14Ai3.1180H11···C3vii3.0516
S1···H14Civ2.8892H11···C4vii2.9005
O1···H3ii2.4806H11···C5vii2.8846
O1···H5vii3.3489H11···C6vii2.9661
O1···H8iii2.6273H11···H4vii3.3789
O1···H9iii3.5684H11···H5vii3.3848
O1···H10iv2.6337H11···H14Axiii3.5203
O1···H11iv3.5544H11···H14Bxiii3.4153
O1···H14Ai3.4300H14A···S1i3.1180
O1···H14Bi2.8025H14A···O1i3.4300
N1···H14Ai3.4407H14A···N1i3.4407
C1···H11iv3.0992H14A···C13i3.1820
C2···H2ii3.4044H14A···C14i3.4899
C2···H3ii3.3218H14A···C14xiii3.3758
C2···H5v3.5950H14A···H11xiii3.5203
C2···H10ix3.5929H14A···H14Ai3.1810
C2···H11iv3.1669H14A···H14Axiii3.2490
C3···H2ii3.1645H14A···H14Bi3.5061
C3···H8v3.5369H14A···H14Cxiii2.7361
C3···H10ix3.3992H14B···O1i2.8025
C3···H11iv3.0516H14B···C10xiii3.0537
C4···H11iv2.9005H14B···C11xiii3.4202
C5···H11iv2.8846H14B···C13i3.0711
C5···H14Civ3.0826H14B···C14i3.4086
C6···H11iv2.9661H14B···H8iii3.1051
C6···H14Civ3.0002H14B···H8xvii3.5810
C7···H3v3.4668H14B···H9iii3.0059
C7···H4v2.9911H14B···H10xiii2.7382
C8···H3v3.0805H14B···H11xiii3.4153
C8···H4v2.9579H14B···H14Ai3.5061
C8···H8i3.0975H14B···H14Bi3.0623
C9···H4v3.0259H14C···S1vii2.8892
C9···H5x3.5246H14C···C5vii3.0826
C9···H9xi3.1910H14C···C6vii3.0002
C10···H2xii3.4004H14C···C14xiii3.2995
C10···H3xii3.5790H14C···H5vii2.9882
C10···H4v3.0919H14C···H9iii3.2172
C10···H9xi3.5933H14C···H14Axiii2.7361
C10···H14Bxiii3.0537H14C···H14Cxiii3.0883
C11···H4v3.0998
C6—S1—C798.29 (7)O1—C13—C14121.79 (11)
C1—N1—C12115.85 (10)N1—C13—C14117.28 (11)
C1—N1—C13119.51 (11)C1—C2—H2120.254
C12—N1—C13123.31 (10)C3—C2—H2120.238
N1—C1—C2122.11 (12)C2—C3—H3119.796
N1—C1—C6117.79 (11)C4—C3—H3119.785
C2—C1—C6120.10 (11)C3—C4—H4119.869
C1—C2—C3119.51 (14)C5—C4—H4119.868
C2—C3—C4120.42 (13)C4—C5—H5120.334
C3—C4—C5120.26 (12)C6—C5—H5120.348
C4—C5—C6119.32 (14)C7—C8—H8120.357
S1—C6—C1119.23 (9)C9—C8—H8120.357
S1—C6—C5120.44 (11)C8—C9—H9119.733
C1—C6—C5120.32 (12)C10—C9—H9119.730
S1—C7—C8120.32 (11)C9—C10—H10119.956
S1—C7—C12119.31 (10)C11—C10—H10119.958
C8—C7—C12120.34 (13)C10—C11—H11120.160
C7—C8—C9119.29 (13)C12—C11—H11120.169
C8—C9—C10120.54 (13)C13—C14—H14A109.468
C9—C10—C11120.09 (15)C13—C14—H14B109.466
C10—C11—C12119.67 (14)C13—C14—H14C109.474
N1—C12—C7117.97 (13)H14A—C14—H14B109.477
N1—C12—C11121.98 (13)H14A—C14—H14C109.471
C7—C12—C11119.99 (12)H14B—C14—H14C109.472
O1—C13—N1120.91 (11)
C6—S1—C7—C8−141.08 (9)C2—C1—C6—S1−179.67 (11)
C6—S1—C7—C1236.99 (9)C2—C1—C6—C5−1.0 (2)
C7—S1—C6—C1−37.65 (11)C6—C1—C2—C32.6 (2)
C7—S1—C6—C5143.66 (10)C1—C2—C3—C4−1.6 (3)
C1—N1—C12—C7−48.72 (16)C2—C3—C4—C5−0.9 (3)
C1—N1—C12—C11128.40 (12)C3—C4—C5—C62.5 (3)
C12—N1—C1—C2−131.80 (13)C4—C5—C6—S1177.10 (12)
C12—N1—C1—C647.89 (17)C4—C5—C6—C1−1.6 (2)
C1—N1—C13—O1−11.7 (2)S1—C7—C8—C9179.29 (7)
C1—N1—C13—C14166.77 (11)S1—C7—C12—N10.64 (15)
C13—N1—C1—C260.91 (18)S1—C7—C12—C11−176.54 (7)
C13—N1—C1—C6−119.41 (13)C8—C7—C12—N1178.71 (10)
C12—N1—C13—O1−177.96 (13)C8—C7—C12—C111.52 (17)
C12—N1—C13—C140.5 (2)C12—C7—C8—C91.24 (17)
C13—N1—C12—C7118.04 (14)C7—C8—C9—C10−2.34 (17)
C13—N1—C12—C11−64.84 (18)C8—C9—C10—C110.68 (18)
N1—C1—C2—C3−177.76 (11)C9—C10—C11—C122.10 (19)
N1—C1—C6—S10.64 (18)C10—C11—C12—N1179.74 (11)
N1—C1—C6—C5179.34 (11)C10—C11—C12—C7−3.19 (18)
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