organic compounds
1-(10H-phenothiazin-10-yl)ethanone
aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama 640-8510, Japan
*Correspondence e-mail: okuno@center.wakayama-u.ac.jp
In the title compound, C14H11NOS, the phenothiazine 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 phenothiazine fragment and the acetyl group.
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
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Data collection: CrystalClear (Rigaku, 2008); cell 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).
Supporting information
10.1107/S1600536812045904/fy2074sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045904/fy2074Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812045904/fy2074Isup3.cml
Single crystals with sufficient quality for X-ray crystallographical analysis were prepared by recrystallization from an ethanol solution.
The C-bound H atoms were placed at ideal positions and were refined as riding on their parent C atoms. Uiso(H) values of the H atoms were set at 1.2Ueq(parent atom).
Data collection: CrystalClear (Rigaku, 2008); cell
CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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).Fig. 1. The asymmetric unit of the title compound with atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres. |
C14H11NOS | F(000) = 1008.00 |
Mr = 241.31 | Dx = 1.421 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -C 2yc | Cell parameters from 3415 reflections |
a = 21.435 (6) Å | θ = 2.1–31.1° |
b = 8.897 (3) Å | µ = 0.27 mm−1 |
c = 12.738 (4) Å | T = 93 K |
β = 111.753 (3)° | Block, colorless |
V = 2256.2 (11) Å3 | 0.17 × 0.10 × 0.10 mm |
Z = 8 |
Rigaku Saturn724+ diffractometer | 2337 reflections with F2 > 2σ(F2) |
Detector resolution: 7.111 pixels mm-1 | Rint = 0.025 |
ω scans | θmax = 27.5° |
Absorption correction: numerical (NUMABS; Rigaku, 1999) | h = −27→27 |
Tmin = 0.969, Tmax = 0.974 | k = −11→8 |
9030 measured reflections | l = −16→16 |
2584 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.042P)2 + 2.3718P] where P = (Fo2 + 2Fc2)/3 |
2584 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C14H11NOS | V = 2256.2 (11) Å3 |
Mr = 241.31 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.435 (6) Å | µ = 0.27 mm−1 |
b = 8.897 (3) Å | T = 93 K |
c = 12.738 (4) Å | 0.17 × 0.10 × 0.10 mm |
β = 111.753 (3)° |
Rigaku Saturn724+ diffractometer | 2584 independent reflections |
Absorption correction: numerical (NUMABS; Rigaku, 1999) | 2337 reflections with F2 > 2σ(F2) |
Tmin = 0.969, Tmax = 0.974 | Rint = 0.025 |
9030 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.31 e Å−3 |
2584 reflections | Δρmin = −0.24 e Å−3 |
154 parameters |
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). |
x | y | z | Uiso*/Ueq | ||
S1 | 0.414831 (16) | 0.27277 (3) | 0.08674 (2) | 0.01289 (10) | |
O1 | 0.39200 (5) | −0.21234 (10) | 0.18741 (8) | 0.0181 (2) | |
N1 | 0.37281 (5) | 0.03491 (12) | 0.20689 (9) | 0.0120 (3) | |
C1 | 0.32864 (6) | 0.04797 (14) | 0.09052 (10) | 0.0118 (3) | |
C2 | 0.27278 (7) | −0.04399 (14) | 0.04325 (11) | 0.0149 (3) | |
C3 | 0.23329 (7) | −0.02967 (15) | −0.07063 (11) | 0.0169 (3) | |
C4 | 0.24838 (7) | 0.07854 (15) | −0.13668 (11) | 0.0163 (3) | |
C5 | 0.30261 (7) | 0.17472 (15) | −0.08875 (11) | 0.0147 (3) | |
C6 | 0.34325 (6) | 0.15792 (14) | 0.02484 (10) | 0.0121 (3) | |
C7 | 0.41033 (6) | 0.29392 (14) | 0.22130 (10) | 0.0113 (3) | |
C8 | 0.42569 (6) | 0.43164 (14) | 0.27746 (11) | 0.0134 (3) | |
C9 | 0.42106 (6) | 0.44609 (15) | 0.38294 (11) | 0.0156 (3) | |
C10 | 0.39899 (7) | 0.32640 (15) | 0.43056 (11) | 0.0165 (3) | |
C11 | 0.38202 (7) | 0.19044 (15) | 0.37316 (11) | 0.0147 (3) | |
C12 | 0.38932 (6) | 0.17307 (14) | 0.26952 (10) | 0.0116 (3) | |
C13 | 0.40672 (6) | −0.09848 (14) | 0.24523 (11) | 0.0132 (3) | |
C14 | 0.46316 (7) | −0.09615 (15) | 0.35876 (11) | 0.0164 (3) | |
H2 | 0.2617 | −0.1161 | 0.0885 | 0.0179* | |
H3 | 0.1957 | −0.0941 | −0.1038 | 0.0202* | |
H4 | 0.2215 | 0.0866 | −0.2148 | 0.0195* | |
H5 | 0.3119 | 0.2512 | −0.1330 | 0.0177* | |
H8 | 0.4392 | 0.5146 | 0.2439 | 0.0161* | |
H9 | 0.4330 | 0.5384 | 0.4229 | 0.0187* | |
H10 | 0.3955 | 0.3376 | 0.5024 | 0.0198* | |
H11 | 0.3655 | 0.1098 | 0.4044 | 0.0176* | |
H14A | 0.4889 | −0.0030 | 0.3668 | 0.0197* | |
H14B | 0.4927 | −0.1826 | 0.3651 | 0.0197* | |
H14C | 0.4447 | −0.1013 | 0.4185 | 0.0197* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01464 (17) | 0.01445 (17) | 0.01035 (15) | −0.00323 (11) | 0.00552 (12) | −0.00079 (11) |
O1 | 0.0196 (5) | 0.0115 (5) | 0.0205 (5) | −0.0003 (4) | 0.0043 (4) | −0.0018 (4) |
N1 | 0.0141 (6) | 0.0110 (5) | 0.0098 (5) | −0.0003 (4) | 0.0031 (5) | 0.0002 (4) |
C1 | 0.0123 (6) | 0.0116 (6) | 0.0110 (6) | 0.0020 (5) | 0.0038 (5) | −0.0008 (5) |
C2 | 0.0141 (6) | 0.0130 (6) | 0.0176 (7) | −0.0003 (5) | 0.0060 (5) | −0.0007 (5) |
C3 | 0.0119 (7) | 0.0161 (6) | 0.0197 (7) | 0.0003 (5) | 0.0025 (6) | −0.0040 (5) |
C4 | 0.0129 (6) | 0.0198 (7) | 0.0129 (6) | 0.0048 (5) | 0.0010 (5) | −0.0031 (5) |
C5 | 0.0164 (7) | 0.0147 (6) | 0.0133 (6) | 0.0035 (5) | 0.0059 (5) | 0.0009 (5) |
C6 | 0.0113 (6) | 0.0116 (6) | 0.0132 (6) | 0.0005 (5) | 0.0045 (5) | −0.0022 (5) |
C7 | 0.0098 (6) | 0.0136 (6) | 0.0101 (6) | 0.0019 (5) | 0.0034 (5) | −0.0005 (5) |
C8 | 0.0108 (6) | 0.0128 (6) | 0.0157 (6) | 0.0001 (5) | 0.0039 (5) | −0.0003 (5) |
C9 | 0.0135 (7) | 0.0155 (6) | 0.0156 (6) | 0.0013 (5) | 0.0027 (5) | −0.0052 (5) |
C10 | 0.0163 (7) | 0.0209 (7) | 0.0122 (6) | 0.0033 (6) | 0.0052 (5) | −0.0019 (5) |
C11 | 0.0143 (6) | 0.0174 (7) | 0.0131 (6) | 0.0007 (5) | 0.0058 (5) | 0.0021 (5) |
C12 | 0.0103 (6) | 0.0116 (6) | 0.0116 (6) | 0.0008 (5) | 0.0026 (5) | −0.0008 (5) |
C13 | 0.0138 (6) | 0.0128 (6) | 0.0146 (6) | −0.0008 (5) | 0.0070 (5) | 0.0022 (5) |
C14 | 0.0171 (7) | 0.0163 (6) | 0.0150 (7) | 0.0014 (5) | 0.0050 (6) | 0.0020 (5) |
S1—C6 | 1.7673 (13) | C9—C10 | 1.392 (2) |
S1—C7 | 1.7621 (15) | C10—C11 | 1.3903 (19) |
O1—C13 | 1.2231 (16) | C11—C12 | 1.394 (3) |
N1—C1 | 1.4376 (15) | C13—C14 | 1.5028 (17) |
N1—C12 | 1.4365 (17) | C2—H2 | 0.950 |
N1—C13 | 1.3828 (16) | C3—H3 | 0.950 |
C1—C2 | 1.3897 (18) | C4—H4 | 0.950 |
C1—C6 | 1.396 (2) | C5—H5 | 0.950 |
C2—C3 | 1.3881 (18) | C8—H8 | 0.950 |
C3—C4 | 1.393 (3) | C9—H9 | 0.950 |
C4—C5 | 1.3893 (19) | C10—H10 | 0.950 |
C5—C6 | 1.3930 (17) | C11—H11 | 0.950 |
C7—C8 | 1.3953 (18) | C14—H14A | 0.980 |
C7—C12 | 1.393 (2) | C14—H14B | 0.980 |
C8—C9 | 1.389 (3) | C14—H14C | 0.980 |
S1···N1 | 2.9418 (14) | C11···H14Bxiii | 3.4202 |
O1···C1 | 2.7367 (16) | C12···H4v | 3.0777 |
O1···C2 | 2.9441 (16) | C13···H3ii | 3.5525 |
O1···C12 | 3.5917 (18) | C13···H5vii | 3.2746 |
C1···C4 | 2.7782 (18) | C13···H8iii | 3.5131 |
C1···C7 | 2.9099 (17) | C13···H14Ai | 3.1820 |
C1···C11 | 3.581 (2) | C13···H14Bi | 3.0711 |
C2···C5 | 2.796 (3) | C14···H5vii | 3.5612 |
C2···C12 | 3.5972 (18) | C14···H9iii | 3.4709 |
C2···C13 | 3.1019 (17) | C14···H10xiii | 3.5985 |
C3···C6 | 2.7741 (19) | C14···H14Ai | 3.4899 |
C6···C12 | 2.903 (2) | C14···H14Axiii | 3.3758 |
C6···C13 | 3.4792 (19) | C14···H14Bi | 3.4086 |
C7···C10 | 2.780 (3) | C14···H14Cxiii | 3.2995 |
C7···C13 | 3.508 (2) | H2···C2ii | 3.4044 |
C8···C11 | 2.795 (2) | H2···C3ii | 3.1645 |
C9···C12 | 2.7789 (19) | H2···C10ix | 3.4004 |
C11···C13 | 3.191 (2) | H2···H2ii | 3.1902 |
C11···C14 | 3.130 (3) | H2···H3ii | 2.7183 |
C12···C14 | 2.8638 (19) | H2···H4vii | 2.9472 |
S1···C8i | 3.5062 (15) | H2···H5vii | 3.5148 |
O1···C3ii | 3.4254 (18) | H2···H10ix | 3.1583 |
O1···C8iii | 3.3551 (17) | H3···O1ii | 2.4806 |
O1···C10iv | 3.481 (2) | H3···C2ii | 3.3218 |
O1···C14i | 3.522 (3) | H3···C7v | 3.4668 |
C3···O1ii | 3.4254 (18) | H3···C8v | 3.0805 |
C3···C8v | 3.5581 (18) | H3···C10ix | 3.5790 |
C4···C7v | 3.362 (2) | H3···C13ii | 3.5525 |
C4···C8v | 3.491 (2) | H3···H2ii | 2.7183 |
C4···C12v | 3.5717 (19) | H3···H5xiv | 3.5725 |
C7···C4v | 3.362 (2) | H3···H8v | 2.8676 |
C8···S1i | 3.5062 (15) | H3···H10ix | 2.7814 |
C8···O1vi | 3.3551 (17) | H4···C7v | 2.9911 |
C8···C3v | 3.5581 (18) | H4···C8v | 2.9579 |
C8···C4v | 3.491 (2) | H4···C9v | 3.0259 |
C8···C8i | 3.506 (3) | H4···C10v | 3.0919 |
C10···O1vii | 3.481 (2) | H4···C11v | 3.0998 |
C12···C4v | 3.5717 (19) | H4···C12v | 3.0777 |
C13···C14i | 3.503 (3) | H4···H2iv | 2.9472 |
C14···O1i | 3.522 (3) | H4···H5xiv | 3.4855 |
C14···C13i | 3.503 (3) | H4···H8v | 3.4440 |
S1···H5 | 2.8571 | H4···H9v | 3.5674 |
S1···H8 | 2.8527 | H4···H11iv | 3.3789 |
O1···H2 | 2.7411 | H5···O1iv | 3.3489 |
O1···H14A | 3.0798 | H5···C2v | 3.5950 |
O1···H14B | 2.4958 | H5···C9viii | 3.5246 |
O1···H14C | 2.9067 | H5···C13iv | 3.2746 |
N1···H2 | 2.6627 | H5···C14iv | 3.5612 |
N1···H11 | 2.6624 | H5···H2iv | 3.5148 |
N1···H14A | 2.5881 | H5···H3xv | 3.5725 |
N1···H14B | 3.2510 | H5···H4xv | 3.4855 |
N1···H14C | 2.8334 | H5···H9viii | 3.0641 |
C1···H3 | 3.2575 | H5···H11iv | 3.3848 |
C1···H5 | 3.2778 | H5···H14Civ | 2.9882 |
C2···H4 | 3.2687 | H8···O1vi | 2.6273 |
C3···H5 | 3.2715 | H8···C3v | 3.5369 |
C4···H2 | 3.2716 | H8···C8i | 3.0975 |
C5···H3 | 3.2680 | H8···C13vi | 3.5131 |
C6···H2 | 3.2727 | H8···H3v | 2.8676 |
C6···H4 | 3.2601 | H8···H4v | 3.4440 |
C7···H9 | 3.2612 | H8···H8i | 2.5542 |
C7···H11 | 3.2720 | H8···H10viii | 3.1524 |
C7···H14A | 3.3070 | H8···H14Bvi | 3.1051 |
C8···H10 | 3.2705 | H8···H14Bxvi | 3.5810 |
C9···H11 | 3.2690 | H9···S1x | 2.8168 |
C10···H8 | 3.2734 | H9···O1vi | 3.5684 |
C11···H9 | 3.2663 | H9···C9xi | 3.1910 |
C11···H14A | 2.8911 | H9···C10xi | 3.5933 |
C11···H14C | 2.8813 | H9···C14vi | 3.4709 |
C12···H8 | 3.2774 | H9···H4v | 3.5674 |
C12···H10 | 3.2657 | H9···H5x | 3.0641 |
C12···H14A | 2.5664 | H9···H9xi | 2.8955 |
C12···H14C | 3.0495 | H9···H14Bvi | 3.0059 |
C13···H2 | 3.0122 | H9···H14Cvi | 3.2172 |
C13···H11 | 3.1065 | H10···O1vii | 2.6337 |
C14···H11 | 2.9960 | H10···C2xii | 3.5929 |
H2···H3 | 2.3388 | H10···C3xii | 3.3992 |
H3···H4 | 2.3384 | H10···C14xiii | 3.5985 |
H4···H5 | 2.3425 | H10···H2xii | 3.1583 |
H8···H9 | 2.3410 | H10···H3xii | 2.7814 |
H9···H10 | 2.3377 | H10···H8x | 3.1524 |
H10···H11 | 2.3422 | H10···H14Bxiii | 2.7382 |
H11···H14A | 3.0286 | H11···O1vii | 3.5544 |
H11···H14C | 2.4928 | H11···C1vii | 3.0992 |
S1···H9viii | 2.8168 | H11···C2vii | 3.1669 |
S1···H14Ai | 3.1180 | H11···C3vii | 3.0516 |
S1···H14Civ | 2.8892 | H11···C4vii | 2.9005 |
O1···H3ii | 2.4806 | H11···C5vii | 2.8846 |
O1···H5vii | 3.3489 | H11···C6vii | 2.9661 |
O1···H8iii | 2.6273 | H11···H4vii | 3.3789 |
O1···H9iii | 3.5684 | H11···H5vii | 3.3848 |
O1···H10iv | 2.6337 | H11···H14Axiii | 3.5203 |
O1···H11iv | 3.5544 | H11···H14Bxiii | 3.4153 |
O1···H14Ai | 3.4300 | H14A···S1i | 3.1180 |
O1···H14Bi | 2.8025 | H14A···O1i | 3.4300 |
N1···H14Ai | 3.4407 | H14A···N1i | 3.4407 |
C1···H11iv | 3.0992 | H14A···C13i | 3.1820 |
C2···H2ii | 3.4044 | H14A···C14i | 3.4899 |
C2···H3ii | 3.3218 | H14A···C14xiii | 3.3758 |
C2···H5v | 3.5950 | H14A···H11xiii | 3.5203 |
C2···H10ix | 3.5929 | H14A···H14Ai | 3.1810 |
C2···H11iv | 3.1669 | H14A···H14Axiii | 3.2490 |
C3···H2ii | 3.1645 | H14A···H14Bi | 3.5061 |
C3···H8v | 3.5369 | H14A···H14Cxiii | 2.7361 |
C3···H10ix | 3.3992 | H14B···O1i | 2.8025 |
C3···H11iv | 3.0516 | H14B···C10xiii | 3.0537 |
C4···H11iv | 2.9005 | H14B···C11xiii | 3.4202 |
C5···H11iv | 2.8846 | H14B···C13i | 3.0711 |
C5···H14Civ | 3.0826 | H14B···C14i | 3.4086 |
C6···H11iv | 2.9661 | H14B···H8iii | 3.1051 |
C6···H14Civ | 3.0002 | H14B···H8xvii | 3.5810 |
C7···H3v | 3.4668 | H14B···H9iii | 3.0059 |
C7···H4v | 2.9911 | H14B···H10xiii | 2.7382 |
C8···H3v | 3.0805 | H14B···H11xiii | 3.4153 |
C8···H4v | 2.9579 | H14B···H14Ai | 3.5061 |
C8···H8i | 3.0975 | H14B···H14Bi | 3.0623 |
C9···H4v | 3.0259 | H14C···S1vii | 2.8892 |
C9···H5x | 3.5246 | H14C···C5vii | 3.0826 |
C9···H9xi | 3.1910 | H14C···C6vii | 3.0002 |
C10···H2xii | 3.4004 | H14C···C14xiii | 3.2995 |
C10···H3xii | 3.5790 | H14C···H5vii | 2.9882 |
C10···H4v | 3.0919 | H14C···H9iii | 3.2172 |
C10···H9xi | 3.5933 | H14C···H14Axiii | 2.7361 |
C10···H14Bxiii | 3.0537 | H14C···H14Cxiii | 3.0883 |
C11···H4v | 3.0998 | ||
C6—S1—C7 | 98.29 (7) | O1—C13—C14 | 121.79 (11) |
C1—N1—C12 | 115.85 (10) | N1—C13—C14 | 117.28 (11) |
C1—N1—C13 | 119.51 (11) | C1—C2—H2 | 120.254 |
C12—N1—C13 | 123.31 (10) | C3—C2—H2 | 120.238 |
N1—C1—C2 | 122.11 (12) | C2—C3—H3 | 119.796 |
N1—C1—C6 | 117.79 (11) | C4—C3—H3 | 119.785 |
C2—C1—C6 | 120.10 (11) | C3—C4—H4 | 119.869 |
C1—C2—C3 | 119.51 (14) | C5—C4—H4 | 119.868 |
C2—C3—C4 | 120.42 (13) | C4—C5—H5 | 120.334 |
C3—C4—C5 | 120.26 (12) | C6—C5—H5 | 120.348 |
C4—C5—C6 | 119.32 (14) | C7—C8—H8 | 120.357 |
S1—C6—C1 | 119.23 (9) | C9—C8—H8 | 120.357 |
S1—C6—C5 | 120.44 (11) | C8—C9—H9 | 119.733 |
C1—C6—C5 | 120.32 (12) | C10—C9—H9 | 119.730 |
S1—C7—C8 | 120.32 (11) | C9—C10—H10 | 119.956 |
S1—C7—C12 | 119.31 (10) | C11—C10—H10 | 119.958 |
C8—C7—C12 | 120.34 (13) | C10—C11—H11 | 120.160 |
C7—C8—C9 | 119.29 (13) | C12—C11—H11 | 120.169 |
C8—C9—C10 | 120.54 (13) | C13—C14—H14A | 109.468 |
C9—C10—C11 | 120.09 (15) | C13—C14—H14B | 109.466 |
C10—C11—C12 | 119.67 (14) | C13—C14—H14C | 109.474 |
N1—C12—C7 | 117.97 (13) | H14A—C14—H14B | 109.477 |
N1—C12—C11 | 121.98 (13) | H14A—C14—H14C | 109.471 |
C7—C12—C11 | 119.99 (12) | H14B—C14—H14C | 109.472 |
O1—C13—N1 | 120.91 (11) | ||
C6—S1—C7—C8 | −141.08 (9) | C2—C1—C6—S1 | −179.67 (11) |
C6—S1—C7—C12 | 36.99 (9) | C2—C1—C6—C5 | −1.0 (2) |
C7—S1—C6—C1 | −37.65 (11) | C6—C1—C2—C3 | 2.6 (2) |
C7—S1—C6—C5 | 143.66 (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—C11 | 128.40 (12) | C3—C4—C5—C6 | 2.5 (3) |
C12—N1—C1—C2 | −131.80 (13) | C4—C5—C6—S1 | 177.10 (12) |
C12—N1—C1—C6 | 47.89 (17) | C4—C5—C6—C1 | −1.6 (2) |
C1—N1—C13—O1 | −11.7 (2) | S1—C7—C8—C9 | 179.29 (7) |
C1—N1—C13—C14 | 166.77 (11) | S1—C7—C12—N1 | 0.64 (15) |
C13—N1—C1—C2 | 60.91 (18) | S1—C7—C12—C11 | −176.54 (7) |
C13—N1—C1—C6 | −119.41 (13) | C8—C7—C12—N1 | 178.71 (10) |
C12—N1—C13—O1 | −177.96 (13) | C8—C7—C12—C11 | 1.52 (17) |
C12—N1—C13—C14 | 0.5 (2) | C12—C7—C8—C9 | 1.24 (17) |
C13—N1—C12—C7 | 118.04 (14) | C7—C8—C9—C10 | −2.34 (17) |
C13—N1—C12—C11 | −64.84 (18) | C8—C9—C10—C11 | 0.68 (18) |
N1—C1—C2—C3 | −177.76 (11) | C9—C10—C11—C12 | 2.10 (19) |
N1—C1—C6—S1 | 0.64 (18) | C10—C11—C12—N1 | 179.74 (11) |
N1—C1—C6—C5 | 179.34 (11) | C10—C11—C12—C7 | −3.19 (18) |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, −y−1/2, −z; (iii) x, y−1, z; (iv) x, −y, z−1/2; (v) −x+1/2, −y+1/2, −z; (vi) x, y+1, z; (vii) x, −y, z+1/2; (viii) x, −y+1, z−1/2; (ix) −x+1/2, y−1/2, −z+1/2; (x) x, −y+1, z+1/2; (xi) −x+1, −y+1, −z+1; (xii) −x+1/2, y+1/2, −z+1/2; (xiii) −x+1, −y, −z+1; (xiv) −x+1/2, y−1/2, −z−1/2; (xv) −x+1/2, y+1/2, −z−1/2; (xvi) −x+1, y+1, −z+1/2; (xvii) −x+1, y−1, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H11NOS |
Mr | 241.31 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 93 |
a, b, c (Å) | 21.435 (6), 8.897 (3), 12.738 (4) |
β (°) | 111.753 (3) |
V (Å3) | 2256.2 (11) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.17 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Rigaku Saturn724+ diffractometer |
Absorption correction | Numerical (NUMABS; Rigaku, 1999) |
Tmin, Tmax | 0.969, 0.974 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 9030, 2584, 2337 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.081, 1.03 |
No. of reflections | 2584 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.24 |
Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), CrystalStructure (Rigaku, 2010).
Acknowledgements
This work was supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).
References
Chu, S. S. C. & Van der Helm, D. (1974). Acta Cryst. B30, 2489–2490. CSD CrossRef IUCr Journals Web of Science Google Scholar
Chu, S. S. C. & Van der Helm, D. (1975). Acta Cryst. B31, 1179–1183. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
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Phenothiazine derivatives have been interesting from the viewpoint of formation of charge-transfer complexes and biochemical reactivities. The title compound is an N-acetylated phenothiazine in which the orientation of the acetyl group is thought to determine the molecular structure and furthermore to affect the oxidation reactivity at 5-position.
The phenothiazine moiety has a butterfly structure, and the central six-membered ring has a boat form. The dihedral angle between the C1—C6 and C7—C12 planes is 133.61 (7)°, which is smaller than a usual angle (Chu & Van der Helm, 1974, 1975). The five atoms of N1, C1, C12, C13 and O1 lie on almost the same plane (the N1/C1/C12/Cl3/O1 plane: r.m.s. deviation = 0.0317 Å), showing efficient conjugation between the lone pair of N1 and the carbonyl group. The proximity of C11 and C14 is indicated by the intramolecular contact distance of 3.130 (3) Å, although little effective contact is observed around O1. The relatively small dihedral angle between the benzene rings is thought to reduce the steric repulsion between the phenothiazine moiety and the acetyl group. There are three reports concerning 1-(10H-phenothiazin-10-yl)ethanone derivatives (Meester & Chu, 1986; Wang et al., 2009; Siddegowda et al., 2011). Similar steric effects can also be recognized in these cases.