10-(2-Eth­oxy-1,3-thia­zol-5-yl)-10-hy­droxy­phenanthren-9(10H)-one

Fun, H.-K.; Goh, J.H.; Liu, Y.; Zhang, Y.

doi:10.1107/S1600536810031004

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2234-o2235

https://doi.org/10.1107/S1600536810031004

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10-(2-Ethoxy-1,3-thiazol-5-yl)-10-hydroxyphenanthren-9(10H)-one

Hoong-Kun Fun,^a ^*‡ Jia Hao Goh,^a § Yang Liu ^b and Yan Zhang ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: hkfun@usm.my

(Received 2 August 2010; accepted 3 August 2010; online 11 August 2010)

In the title compound, C₁₉H₁₅NO₃S, the dihydrophenanthrene unit is not planar, its central ring being distorted towards a sofa conformation. The essentially planar thiazole ring [maximum deviation = 0.005 (1) Å] is inclined at a dihedral angle of 85.29 (5)° with respect to the mean plane formed through the dihydrophenanthrene unit. In the crystal structure, pairs of intermolecular C—H⋯O hydrogen bonds link adjacent molecules into inversion dimers. Intermolecular O—H⋯N hydrogen bonds further interconnect these dimers into chains along the a axis. The crystal structure is further stabilized by weak intermolecular C—H⋯π interactions involving the thiazole ring.

Related literature

For general background to and applications of phenanthrenone derivatives, see: Schuetzle (1983 ); Cho et al. (2004 ); Lim et al. (1998 ); Sanbongi et al. (2003 ); Shurygina et al. (2008 ); Zhang et al. (2004 ); Lichtenthaler et al. (2004 ); Cutignano et al. (2001 ); Williams et al. (2001 ); DeRoy & Charette (2003 ); Yoshimura et al. (1995 ); Tsuruni et al. (1995 ); Gao et al. (2010 ); Shi et al. (2010 ); Kaleta et al. (2006 ). For ring conformations, see: Cremer & Pople (1975 ). For a closely related phenanthrenone structure, see: Wang et al. (2003 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₉H₁₅NO₃S
M_r = 337.38
Triclinic, $[P \overline 1]$
a = 7.1386 (4) Å
b = 9.6206 (6) Å
c = 12.7743 (8) Å
α = 106.863 (2)°
β = 97.746 (2)°
γ = 104.667 (2)°
V = 791.41 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.40 × 0.31 × 0.20 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.916, T_max = 0.958
16288 measured reflections
4157 independent reflections
3811 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.139
S = 1.12
4157 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the thiazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N1ⁱ	0.87 (3)	2.08 (3)	2.8643 (18)	149 (2)
C12—H12A⋯O3ⁱⁱ	0.93	2.52	3.4395 (18)	170
C4—H4A⋯Cg1ⁱⁱⁱ	0.93	2.70	3.563	155
Symmetry codes: (i) x+1, y, z; (ii) -x, -y, -z; (iii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810031004/bt5320sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031004/bt5320Isup2.hkl

checkCIF report

Comment top

Phenanthraquinone and its derivatives have shown diverse applications and biological activities (Schuetzle, 1983; Cho et al., 2004; Lim et al., 1998; Sanbongi et al., 2003). 9,10-Phenanthraquinone has been used as o-quinone in photoreactions with various species (Shurygina et al., 2008; Zhang et al., 2004; Lichtenthaler et al., 2004). Thiazole-containing compounds, such as the mycothiazole (Cutignano et al.,2001), cystothiazole A (Williams et al.,2001; DeRoy & Charette,2003) and WS75624 B (Yoshimura et al.,1995; Tsuruni et al.,1995) have attracted considerable interest due to their potential application as bio-active species. Synthesis of organic molecules containing thiazole moieties therefore has been of current research interest (Gao et al.,2010; Shi et al.,2010; Kaleta et al.,2006). The title compound which contains phenanthraquinone and thiazole ring may has a potential use in biochemical and pharmaceutical fields. Due to the importance of the phenanthraquinone derivaties, we report in this paper the crystal structure of the title compound.

In the title phenanthraquinone compound (Fig. 1), the 1,2-dihydrobenzene ring (C1/C2/C7/C8/C13/C14) of the 9,10-dihydrophenanthrene ring system (C1-C14) adopts a sofa conformation, with atoms C1 and C14 deviating from the mean plane through the remaning four atoms in opposite directions by 0.1244 (15) and -0.3597 (15) Å, respectively. The puckering parameters are Q = 0.3293 (16) Å, θ = 67.0 (3)° and φ = 317.5 (3)° (Cremer & Pople, 1975). The thiazole ring (C15/C16/N1/C17/S1) is essentially planar, with a maximum deviation of 0.005 (1) Å at atom C17. The mean plane formed through the 9,10-dihydrophenanthrene ring system is approximately perpendicular to the thiazole ring, as indicated by the dihedral angle formed between them being 85.29 (5)°. The geometric parameters are consistent with those observed in closely related 9,10-dihydrophenanthrenone structures (Wang et al., 2003).

In the crystal structure (Fig. 2), adjacent molecules are linked into dimers by pairs of intermolecular C12—H12A···O3 hydrogen bonds (Table 1). These dimers are interconnected by O2—H1O2···N1 hydrogen bonds (Table 1) into two-molecule-wide chains propagating along the a axis. Further stabilization of the crystal structure is provided by weak intermolecular C4—H4A···Cg1 interactions (Table 1) involving the centroid of the thiazole ring.

Related literature top

For general background to and applications of phenanthrenone derivatives, see: Schuetzle (1983); Cho et al. (2004); Lim et al. (1998); Sanbongi et al. (2003); Shurygina et al. (2008); Zhang et al. (2004); Lichtenthaler et al. (2004); Cutignano et al. (2001); Williams et al. (2001); DeRoy & Charette (2003); Yoshimura et al. (1995); Tsuruni et al. (1995); Gao et al. (2010); Shi et al. (2010); Kaleta et al. (2006). For ring conformations, see: Cremer & Pople (1975). For closely related phenanthrenone structures, see: Wang et al. (2003). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was one of the products from the photoreaction between phenanthraquinone and 2-ethoxylthiazole. The compound was purified by flash column chromatography with ethyl acetate/petroleum ether (1:4) as eluents. X-ray quality single crystals of the title compound were obtained from slow evaporation of an acetone and petroleum ether (1:5) solution. M.p. 410–412 K.

Structure description top

For general background to and applications of phenanthrenone derivatives, see: Schuetzle (1983); Cho et al. (2004); Lim et al. (1998); Sanbongi et al. (2003); Shurygina et al. (2008); Zhang et al. (2004); Lichtenthaler et al. (2004); Cutignano et al. (2001); Williams et al. (2001); DeRoy & Charette (2003); Yoshimura et al. (1995); Tsuruni et al. (1995); Gao et al. (2010); Shi et al. (2010); Kaleta et al. (2006). For ring conformations, see: Cremer & Pople (1975). For closely related phenanthrenone structures, see: Wang et al. (2003). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis, showing the molecules being linked into chains along the a axis.

10-(2-Ethoxy-1,3-thiazol-5-yl)-10-hydroxyphenanthren-9(10H)-one top

Crystal data top

C₁₉H₁₅NO₃S	Z = 2
M_r = 337.38	F(000) = 352
Triclinic, P1	D_x = 1.416 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1386 (4) Å	Cell parameters from 9610 reflections
b = 9.6206 (6) Å	θ = 3.0–35.0°
c = 12.7743 (8) Å	µ = 0.22 mm⁻¹
α = 106.863 (2)°	T = 100 K
β = 97.746 (2)°	Block, colourless
γ = 104.667 (2)°	0.40 × 0.31 × 0.20 mm
V = 791.41 (8) Å³

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	4157 independent reflections
Radiation source: fine-focus sealed tube	3811 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
φ and ω scans	θ_max = 29.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.916, T_max = 0.958	k = −13→13
16288 measured reflections	l = −17→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.086P)² + 0.3384P] where P = (F_o² + 2F_c²)/3
4157 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.96 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₉H₁₅NO₃S	γ = 104.667 (2)°
M_r = 337.38	V = 791.41 (8) Å³
Triclinic, P1	Z = 2
a = 7.1386 (4) Å	Mo Kα radiation
b = 9.6206 (6) Å	µ = 0.22 mm⁻¹
c = 12.7743 (8) Å	T = 100 K
α = 106.863 (2)°	0.40 × 0.31 × 0.20 mm
β = 97.746 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	4157 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3811 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.958	R_int = 0.023
16288 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.96 e Å⁻³
4157 reflections	Δρ_min = −0.51 e Å⁻³
222 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	U_iso*/U_eq
S1	−0.03580 (5)	−0.12894 (4)	0.11117 (3)	0.01623 (12)
O1	0.39811 (18)	−0.00646 (13)	0.31190 (10)	0.0235 (2)
O2	0.36598 (16)	0.12494 (13)	0.15415 (9)	0.0185 (2)
O3	−0.42108 (15)	−0.26001 (11)	0.04040 (8)	0.0161 (2)
N1	−0.30774 (17)	0.00285 (13)	0.14259 (9)	0.0143 (2)
C1	0.3195 (2)	0.09376 (16)	0.33170 (11)	0.0154 (3)
C2	0.2699 (2)	0.15724 (15)	0.44016 (11)	0.0145 (3)
C3	0.2670 (2)	0.07575 (17)	0.51513 (12)	0.0181 (3)
H3A	0.2985	−0.0151	0.4963	0.022*
C4	0.2174 (2)	0.12966 (18)	0.61688 (12)	0.0213 (3)
H4A	0.2149	0.0754	0.6665	0.026*
C5	0.1715 (2)	0.26594 (19)	0.64427 (12)	0.0234 (3)
H5A	0.1340	0.3011	0.7116	0.028*
C6	0.1809 (2)	0.35008 (17)	0.57240 (12)	0.0204 (3)
H6A	0.1531	0.4424	0.5932	0.024*
C7	0.23147 (19)	0.29845 (15)	0.46916 (11)	0.0143 (3)
C8	0.2552 (2)	0.38983 (16)	0.39351 (11)	0.0153 (3)
C9	0.2628 (2)	0.54351 (17)	0.42843 (13)	0.0202 (3)
H9A	0.2493	0.5897	0.5006	0.024*
C10	0.2901 (2)	0.62833 (17)	0.35718 (14)	0.0228 (3)
H10A	0.2936	0.7301	0.3816	0.027*
C11	0.3123 (2)	0.56129 (18)	0.24976 (14)	0.0230 (3)
H11A	0.3321	0.6184	0.2024	0.028*
C12	0.3050 (2)	0.40867 (17)	0.21277 (13)	0.0191 (3)
H12A	0.3189	0.3637	0.1405	0.023*
C13	0.2769 (2)	0.32302 (16)	0.28379 (12)	0.0151 (3)
C14	0.2567 (2)	0.15402 (15)	0.23775 (11)	0.0140 (3)
C15	0.0382 (2)	0.06559 (15)	0.18794 (11)	0.0139 (3)
C16	−0.1246 (2)	0.11260 (15)	0.19485 (11)	0.0151 (3)
H16A	−0.1142	0.2136	0.2328	0.018*
C17	−0.2804 (2)	−0.12792 (15)	0.09691 (11)	0.0134 (2)
C18	−0.6223 (2)	−0.24987 (16)	0.01743 (12)	0.0168 (3)
H18A	−0.6257	−0.1734	−0.0177	0.020*
H18B	−0.6678	−0.2221	0.0866	0.020*
C19	−0.7522 (2)	−0.40515 (19)	−0.06037 (15)	0.0277 (3)
H19A	−0.8874	−0.4047	−0.0758	0.042*
H19B	−0.7438	−0.4801	−0.0256	0.042*
H19C	−0.7082	−0.4296	−0.1293	0.042*
H1O2	0.446 (4)	0.075 (3)	0.170 (2)	0.046 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01308 (18)	0.01435 (18)	0.02028 (19)	0.00675 (13)	0.00430 (13)	0.00202 (13)
O1	0.0287 (6)	0.0282 (6)	0.0238 (5)	0.0196 (5)	0.0105 (4)	0.0121 (4)
O2	0.0193 (5)	0.0265 (5)	0.0193 (5)	0.0148 (4)	0.0105 (4)	0.0122 (4)
O3	0.0133 (5)	0.0149 (5)	0.0187 (5)	0.0051 (4)	0.0016 (4)	0.0042 (4)
N1	0.0137 (5)	0.0156 (5)	0.0150 (5)	0.0066 (4)	0.0038 (4)	0.0052 (4)
C1	0.0134 (6)	0.0174 (6)	0.0160 (6)	0.0051 (5)	0.0032 (5)	0.0060 (5)
C2	0.0120 (6)	0.0160 (6)	0.0143 (6)	0.0041 (5)	0.0023 (4)	0.0038 (5)
C3	0.0163 (6)	0.0181 (6)	0.0192 (6)	0.0046 (5)	0.0019 (5)	0.0070 (5)
C4	0.0214 (7)	0.0250 (7)	0.0165 (6)	0.0034 (6)	0.0025 (5)	0.0096 (5)
C5	0.0257 (8)	0.0275 (7)	0.0146 (6)	0.0056 (6)	0.0068 (5)	0.0050 (6)
C6	0.0230 (7)	0.0202 (6)	0.0176 (6)	0.0086 (5)	0.0066 (5)	0.0032 (5)
C7	0.0118 (6)	0.0164 (6)	0.0139 (6)	0.0046 (5)	0.0019 (5)	0.0041 (5)
C8	0.0110 (6)	0.0172 (6)	0.0175 (6)	0.0051 (5)	0.0013 (5)	0.0060 (5)
C9	0.0191 (7)	0.0174 (6)	0.0216 (7)	0.0065 (5)	0.0010 (5)	0.0037 (5)
C10	0.0201 (7)	0.0160 (6)	0.0304 (8)	0.0057 (5)	0.0004 (6)	0.0071 (6)
C11	0.0221 (7)	0.0211 (7)	0.0272 (7)	0.0053 (6)	0.0028 (6)	0.0127 (6)
C12	0.0181 (6)	0.0206 (7)	0.0204 (6)	0.0065 (5)	0.0038 (5)	0.0094 (5)
C13	0.0116 (6)	0.0170 (6)	0.0181 (6)	0.0059 (5)	0.0031 (5)	0.0072 (5)
C14	0.0133 (6)	0.0166 (6)	0.0142 (6)	0.0069 (5)	0.0042 (5)	0.0061 (5)
C15	0.0142 (6)	0.0137 (6)	0.0141 (6)	0.0053 (5)	0.0042 (5)	0.0038 (4)
C16	0.0148 (6)	0.0147 (6)	0.0169 (6)	0.0068 (5)	0.0039 (5)	0.0050 (5)
C17	0.0132 (6)	0.0162 (6)	0.0126 (5)	0.0062 (5)	0.0034 (4)	0.0056 (5)
C18	0.0127 (6)	0.0193 (6)	0.0195 (6)	0.0060 (5)	0.0028 (5)	0.0077 (5)
C19	0.0177 (7)	0.0236 (7)	0.0327 (8)	0.0031 (6)	−0.0008 (6)	0.0020 (6)

Geometric parameters (Å, º) top

S1—C17	1.7335 (14)	C7—C8	1.4821 (19)
S1—C15	1.7430 (14)	C8—C9	1.3994 (19)
O1—C1	1.2161 (18)	C8—C13	1.4100 (19)
O2—C14	1.4105 (16)	C9—C10	1.389 (2)
O2—H1O2	0.87 (3)	C9—H9A	0.9300
O3—C17	1.3308 (16)	C10—C11	1.386 (2)
O3—C18	1.4606 (17)	C10—H10A	0.9300
N1—C17	1.3003 (17)	C11—C12	1.391 (2)
N1—C16	1.3880 (17)	C11—H11A	0.9300
C1—C2	1.4728 (19)	C12—C13	1.3933 (19)
C1—C14	1.5388 (19)	C12—H12A	0.9300
C2—C3	1.4019 (19)	C13—C14	1.5211 (19)
C2—C7	1.4079 (19)	C14—C15	1.5189 (19)
C3—C4	1.382 (2)	C15—C16	1.3543 (19)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.390 (2)	C18—C19	1.506 (2)
C4—H4A	0.9300	C18—H18A	0.9700
C5—C6	1.387 (2)	C18—H18B	0.9700
C5—H5A	0.9300	C19—H19A	0.9600
C6—C7	1.3984 (19)	C19—H19B	0.9600
C6—H6A	0.9300	C19—H19C	0.9600

C17—S1—C15	88.43 (6)	C10—C11—H11A	120.0
C14—O2—H1O2	110.0 (18)	C12—C11—H11A	120.0
C17—O3—C18	115.16 (11)	C11—C12—C13	120.15 (14)
C17—N1—C16	109.10 (11)	C11—C12—H12A	119.9
O1—C1—C2	123.78 (13)	C13—C12—H12A	119.9
O1—C1—C14	119.33 (12)	C12—C13—C8	120.47 (13)
C2—C1—C14	116.81 (12)	C12—C13—C14	118.51 (12)
C3—C2—C7	120.73 (13)	C8—C13—C14	120.90 (12)
C3—C2—C1	118.45 (13)	O2—C14—C15	109.48 (11)
C7—C2—C1	120.80 (12)	O2—C14—C13	111.05 (11)
C4—C3—C2	120.36 (14)	C15—C14—C13	108.38 (11)
C4—C3—H3A	119.8	O2—C14—C1	110.69 (11)
C2—C3—H3A	119.8	C15—C14—C1	105.45 (11)
C3—C4—C5	119.26 (13)	C13—C14—C1	111.60 (11)
C3—C4—H4A	120.4	C16—C15—C14	130.07 (12)
C5—C4—H4A	120.4	C16—C15—S1	109.29 (10)
C6—C5—C4	120.78 (14)	C14—C15—S1	120.62 (10)
C6—C5—H5A	119.6	C15—C16—N1	116.81 (12)
C4—C5—H5A	119.6	C15—C16—H16A	121.6
C5—C6—C7	121.10 (14)	N1—C16—H16A	121.6
C5—C6—H6A	119.5	N1—C17—O3	126.45 (12)
C7—C6—H6A	119.5	N1—C17—S1	116.37 (10)
C6—C7—C2	117.69 (13)	O3—C17—S1	117.18 (10)
C6—C7—C8	122.51 (13)	O3—C18—C19	106.62 (12)
C2—C7—C8	119.73 (12)	O3—C18—H18A	110.4
C9—C8—C13	118.16 (13)	C19—C18—H18A	110.4
C9—C8—C7	122.03 (13)	O3—C18—H18B	110.4
C13—C8—C7	119.79 (12)	C19—C18—H18B	110.4
C10—C9—C8	121.18 (14)	H18A—C18—H18B	108.6
C10—C9—H9A	119.4	C18—C19—H19A	109.5
C8—C9—H9A	119.4	C18—C19—H19B	109.5
C11—C10—C9	120.00 (14)	H19A—C19—H19B	109.5
C11—C10—H10A	120.0	C18—C19—H19C	109.5
C9—C10—H10A	120.0	H19A—C19—H19C	109.5
C10—C11—C12	120.05 (14)	H19B—C19—H19C	109.5

O1—C1—C2—C3	−16.1 (2)	C12—C13—C14—O2	30.47 (17)
C14—C1—C2—C3	160.58 (12)	C8—C13—C14—O2	−153.54 (12)
O1—C1—C2—C7	162.22 (14)	C12—C13—C14—C15	−89.82 (15)
C14—C1—C2—C7	−21.08 (18)	C8—C13—C14—C15	86.17 (15)
C7—C2—C3—C4	2.9 (2)	C12—C13—C14—C1	154.49 (12)
C1—C2—C3—C4	−178.75 (13)	C8—C13—C14—C1	−29.51 (17)
C2—C3—C4—C5	−0.3 (2)	O1—C1—C14—O2	−22.47 (18)
C3—C4—C5—C6	−2.0 (2)	C2—C1—C14—O2	160.67 (11)
C4—C5—C6—C7	1.8 (2)	O1—C1—C14—C15	95.84 (15)
C5—C6—C7—C2	0.8 (2)	C2—C1—C14—C15	−81.02 (14)
C5—C6—C7—C8	−176.09 (13)	O1—C1—C14—C13	−146.70 (13)
C3—C2—C7—C6	−3.1 (2)	C2—C1—C14—C13	36.44 (16)
C1—C2—C7—C6	178.58 (12)	O2—C14—C15—C16	−131.81 (15)
C3—C2—C7—C8	173.88 (12)	C13—C14—C15—C16	−10.54 (19)
C1—C2—C7—C8	−4.43 (19)	C1—C14—C15—C16	109.08 (16)
C6—C7—C8—C9	11.4 (2)	O2—C14—C15—S1	50.22 (14)
C2—C7—C8—C9	−165.45 (13)	C13—C14—C15—S1	171.49 (9)
C6—C7—C8—C13	−170.55 (13)	C1—C14—C15—S1	−68.89 (13)
C2—C7—C8—C13	12.60 (19)	C17—S1—C15—C16	−0.46 (10)
C13—C8—C9—C10	0.3 (2)	C17—S1—C15—C14	177.89 (11)
C7—C8—C9—C10	178.36 (13)	C14—C15—C16—N1	−178.05 (12)
C8—C9—C10—C11	−0.6 (2)	S1—C15—C16—N1	0.10 (15)
C9—C10—C11—C12	0.7 (2)	C17—N1—C16—C15	0.48 (17)
C10—C11—C12—C13	−0.5 (2)	C16—N1—C17—O3	179.32 (12)
C11—C12—C13—C8	0.2 (2)	C16—N1—C17—S1	−0.87 (14)
C11—C12—C13—C14	176.17 (13)	C18—O3—C17—N1	7.77 (19)
C9—C8—C13—C12	0.0 (2)	C18—O3—C17—S1	−172.05 (9)
C7—C8—C13—C12	−178.18 (12)	C15—S1—C17—N1	0.80 (11)
C9—C8—C13—C14	−175.96 (13)	C15—S1—C17—O3	−179.37 (11)
C7—C8—C13—C14	5.91 (19)	C17—O3—C18—C19	171.99 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the thiazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1ⁱ	0.87 (3)	2.08 (3)	2.8643 (18)	149 (2)
C12—H12A···O3ⁱⁱ	0.93	2.52	3.4395 (18)	170
C4—H4A···Cg1ⁱⁱⁱ	0.93	2.70	3.563	155

Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z; (iii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅NO₃S
M_r	337.38
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.1386 (4), 9.6206 (6), 12.7743 (8)
α, β, γ (°)	106.863 (2), 97.746 (2), 104.667 (2)
V (Å³)	791.41 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.40 × 0.31 × 0.20

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.916, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	16288, 4157, 3811
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.139, 1.12
No. of reflections	4157
No. of parameters	222
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.96, −0.51

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the thiazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1ⁱ	0.87 (3)	2.08 (3)	2.8643 (18)	149 (2)
C12—H12A···O3ⁱⁱ	0.9300	2.5200	3.4395 (18)	170.00
C4—H4A···Cg1ⁱⁱⁱ	0.930	2.699	3.563	155

Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z; (iii) −x, −y, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7576-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for a Research University Golden Goose grant (No. 1001/PFIZIK/811012). Financial support from the Ministry of Science and Technology of China of the Austria–China Cooperation project (2007DFA41590) is acknowledged. JHG also thanks USM for the award of a USM fellowship.

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Volume 66| Part 9| September 2010| Pages o2234-o2235

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