10-Hy­droxy-10-(1,3-thia­zol-2-ylmeth­yl)phenanthren-9(10H)-one

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

doi:10.1107/S1600536810022439

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1683-o1684

doi:10.1107/S1600536810022439

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10-Hydroxy-10-(1,3-thiazol-2-ylmethyl)phenanthren-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 8 June 2010; accepted 11 June 2010; online 16 June 2010)

In the title phenanthrenone compound, C₁₈H₁₃NO₂S, the dihydrophenanthrene ring system is not planar, with its central ring distorted to a screw-boat conformation. The essentially planar thiazole ring [maximum deviation = 0.005 (1) Å] is inclined at an interplanar angle of 23.36 (5)° with respect to the mean plane through the dihydrophenanthrene ring system. In the crystal packing, intermolecular O—H⋯N hydrogen bonds link the molecules into infinite chains along the a axis. Weak intermolecular C—H⋯π interactions further stabilize the crystal packing.

Related literature

For general background to and applications of phenanthrenone derivatives, see: Bloom (1961 ); Kumagai et al. (1997 ); McClellan (1987 ); Meyer & Spengler (1905 ); Milko & Roithova (2009 ); Mustafa et al. (1956 ); Nel et al. (2001 ); Schuetzle et al. (1981 ); Shimada et al. (2004 ); Zhang et al. (2004 ). For ring conformations, see: Cremer & Pople (1975 ). For related structures, see: Jones et al. (2002 ); Li et al. (2003 ); Sun et al. (2007 ); Wang et al. (2003 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₈H₁₃NO₂S
M_r = 307.35
Orthorhombic, P n a 2₁
a = 12.5623 (17) Å
b = 7.3222 (10) Å
c = 15.462 (2) Å
V = 1422.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 100 K
0.33 × 0.17 × 0.17 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.926, T_max = 0.962
14577 measured reflections
3814 independent reflections
3635 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.074
S = 1.03
3814 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1674 Friedel pairs
Flack parameter: 0.04 (5)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of C8–C13 and C2–C7 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N1ⁱ	0.80 (2)	1.976 (19)	2.7542 (14)	165 (2)
C5—H5A⋯Cg1ⁱⁱ	0.93	2.83	3.6508 (16)	147
C12—H12A⋯Cg2ⁱⁱⁱ	0.93	2.85	3.7214 (15)	156
C18—H18A⋯Cg1^iv	0.93	2.72	3.3301 (16)	124
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (ii) $[-x-{\script{1\over 2}}, y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+1, -y+1, z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536810022439/wn2393sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022439/wn2393Isup2.hkl

checkCIF report

Comment top

Research interest in phenanthrenequinone can be traced back as early as 1905 (Bloom, 1961; Meyer & Spengler, 1905). Phenanthrenequinone and its derivatives possess a wide range of activities, especially biological and pharmaceutical. For example, phenanthrenequinone is one of the major quinones in diesel exhaust particles (Milko & Roithova, 2009), which plays a negative role in inducing pathogenic processes such as lung cancer (Schuetzle et al., 1981), allergies (McClellan, 1987) or asthma (Nel et al., 2001). Phenanthrenequinone has also been reported to be a good substrate for microsomal NADPH-cytochrome P450 reductase and that superoxide and hydroxyl radicals generated during redox cycling of the quinone by this flavin enzyme mainly participate in the DEP-prompted oxidative stress (Shimada et al., 2004; Kumagai et al., 1997). The photochemistry of phenanthrenequinone has been investigated early in 1956 (Mustafa et al., 1956). In recent years, more complex products have been obtained in photoreactions of oxazoles with phenanthrenequinone (Zhang et al., 2004). The crystal structures of 2-(4-hydroxy-3,5-dimethoxyphenyl)-1H-phenanthro[9,10-d]imidazole methanol solvate (Sun et al., 2007) and 2,2,2-tris(cyclohexyloxy)-4,5-(2',2''-biphenylo)-1,3,2-dioxaphospholene (Jones et al., 2002) have been reported. Due to the importance of phenanthraquinone derivatives, we report here the crystal structure of the title compound.

In the title compound (Fig. 1), the 1,2-dihydrobenzene ring (C1/C2/C7/C8/C13/C14) of the 9,10-dihydrophenanthrene ring system (C1-C14) is distorted towards a screw-boat conformation as observed in a previously reported structure (Wang et al., 2003), with puckering parameters of Q = 0.4466 (13) Å, θ = 67.55 (18)° and ϕ = 320.40 (19)° (Cremer & Pople, 1975). In the 1,2-dihydrobenzene ring, atoms C1 and C14 deviate by 0.2034 (13) and -0.4508 (12) Å, respectively, in opposite directions from the mean plane through the remaining four atoms. The thiazole ring (C16/N1/C17/C18/S1) is essentially planar, with a maximum deviation of 0.005 (1) Å at atom C16. The interplanar angle formed between the thiazole ring and the mean plane through the 9,10-dihydrophenanthrene ring system is 23.36 (5)°. The geometric parameters are consistent with those observed in closely related 9,10-dihydrophenanthrenone structures (Wang et al., 2003; Li et al., 2003).

In the crystal packing, intermolecular O2—H1O2···N1 hydrogen bonds (Table 1) link the molecules into one-dimensional chains along the [100] direction (Fig. 2). The crystal packing is further stabilized by weak intermolecular C5—H5A···Cg1, C12—H12A···Cg2 and C18—H18A···Cg1 interactions (Table 1), where Cg1 and Cg2 are the centroids of C8-C13 and C2-C7 benzene rings, respectively.

Related literature top

For general background to and applications of phenanthrenone derivatives, see: Bloom (1961); Kumagai et al. (1997); McClellan (1987); Meyer & Spengler (1905); Milko & Roithova (2009); Mustafa et al. (1956); Nel et al. (2001); Schuetzle et al. (1981); Shimada et al. (2004); Zhang et al. (2004). For ring conformations, see: Cremer & Pople (1975). For related structures, see: Jones et al. (2002); Li et al. (2003); Sun et al. (2007); Wang et al. (2003). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was one of the products from the photoreaction between phenanthrenequinone (1 mmol) and 2-methylthiazole (4 mmol) in acetonitrile (50 ml). 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:petroleum ether (1:5) solution. M.p. 430–432 K.

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 hydrogen-bonded (dashed lines) one-dimensional chains along the a axis.

10-Hydroxy-10-(1,3-thiazol-2-ylmethyl)phenanthren-9(10H)-one top

Crystal data top

C₁₈H₁₃NO₂S	F(000) = 640
M_r = 307.35	D_x = 1.435 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 7790 reflections
a = 12.5623 (17) Å	θ = 3.1–30.1°
b = 7.3222 (10) Å	µ = 0.23 mm⁻¹
c = 15.462 (2) Å	T = 100 K
V = 1422.3 (3) Å³	Block, colourless
Z = 4	0.33 × 0.17 × 0.17 mm

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3814 independent reflections
Radiation source: fine-focus sealed tube	3635 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 30.1°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
T_min = 0.926, T_max = 0.962	k = −10→9
14577 measured reflections	l = −17→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0445P)² + 0.2177P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3814 reflections	Δρ_max = 0.32 e Å⁻³
203 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1674 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (5)

Crystal data top

C₁₈H₁₃NO₂S	V = 1422.3 (3) Å³
M_r = 307.35	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.5623 (17) Å	µ = 0.23 mm⁻¹
b = 7.3222 (10) Å	T = 100 K
c = 15.462 (2) Å	0.33 × 0.17 × 0.17 mm

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3814 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3635 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.962	R_int = 0.028
14577 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.074	Δρ_max = 0.32 e Å⁻³
S = 1.03	Δρ_min = −0.21 e Å⁻³
3814 reflections	Absolute structure: Flack (1983), 1674 Friedel pairs
203 parameters	Absolute structure parameter: 0.04 (5)
1 restraint

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	0.53518 (2)	0.49600 (5)	0.78827 (3)	0.02005 (8)
O1	0.58478 (9)	0.98317 (13)	0.74430 (7)	0.0204 (2)
O2	0.68596 (7)	0.68224 (13)	0.67503 (6)	0.01555 (18)
N1	0.36431 (8)	0.62424 (14)	0.72334 (7)	0.0147 (2)
C1	0.56431 (10)	0.94441 (17)	0.66980 (9)	0.0141 (2)
C2	0.48837 (10)	1.05126 (17)	0.61503 (9)	0.0141 (2)
C3	0.40687 (10)	1.14942 (18)	0.65511 (9)	0.0175 (2)
H3A	0.4023	1.1531	0.7151	0.021*
C4	0.33251 (11)	1.24171 (19)	0.60461 (10)	0.0204 (3)
H4A	0.2769	1.3048	0.6307	0.025*
C5	0.34165 (11)	1.23923 (19)	0.51504 (10)	0.0211 (3)
H5A	0.2923	1.3021	0.4816	0.025*
C6	0.42365 (10)	1.14409 (18)	0.47484 (9)	0.0181 (3)
H6A	0.4289	1.1443	0.4148	0.022*
C7	0.49871 (10)	1.04759 (17)	0.52450 (8)	0.0145 (2)
C8	0.59038 (10)	0.95064 (18)	0.48531 (8)	0.0137 (2)
C9	0.62580 (11)	0.98991 (18)	0.40142 (9)	0.0165 (2)
H9A	0.5878	1.0717	0.3673	0.020*
C10	0.71727 (10)	0.90792 (19)	0.36852 (9)	0.0182 (3)
H10A	0.7404	0.9362	0.3130	0.022*
C11	0.77403 (10)	0.78396 (19)	0.41853 (9)	0.0178 (2)
H11A	0.8355	0.7303	0.3967	0.021*
C12	0.73877 (10)	0.74002 (18)	0.50145 (9)	0.0155 (2)
H12A	0.7761	0.6554	0.5345	0.019*
C13	0.64729 (9)	0.82280 (17)	0.53514 (8)	0.0133 (2)
C14	0.60853 (9)	0.77241 (17)	0.62538 (8)	0.0129 (2)
C15	0.51421 (10)	0.63447 (17)	0.61865 (8)	0.0141 (2)
H15A	0.4604	0.6844	0.5804	0.017*
H15B	0.5398	0.5216	0.5933	0.017*
C16	0.46450 (9)	0.59352 (16)	0.70480 (8)	0.0136 (2)
C17	0.34056 (11)	0.56729 (19)	0.80632 (9)	0.0183 (3)
H17A	0.2727	0.5786	0.8298	0.022*
C18	0.42275 (12)	0.49388 (19)	0.85133 (10)	0.0196 (3)
H18A	0.4188	0.4494	0.9076	0.024*
H1O2	0.7346 (14)	0.751 (3)	0.6817 (12)	0.021 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01201 (13)	0.02777 (17)	0.02038 (16)	0.00009 (11)	−0.00259 (13)	0.01058 (13)
O1	0.0226 (5)	0.0242 (5)	0.0144 (5)	0.0006 (4)	−0.0024 (4)	−0.0021 (4)
O2	0.0109 (4)	0.0177 (4)	0.0181 (4)	−0.0014 (3)	−0.0036 (3)	0.0040 (3)
N1	0.0123 (5)	0.0154 (5)	0.0162 (5)	−0.0003 (4)	−0.0006 (4)	0.0018 (4)
C1	0.0112 (5)	0.0160 (5)	0.0151 (6)	−0.0008 (4)	0.0008 (4)	0.0009 (5)
C2	0.0136 (5)	0.0141 (6)	0.0146 (6)	−0.0009 (4)	−0.0010 (4)	−0.0002 (4)
C3	0.0171 (6)	0.0169 (6)	0.0186 (6)	−0.0006 (5)	0.0023 (5)	−0.0023 (5)
C4	0.0161 (6)	0.0169 (6)	0.0283 (7)	0.0022 (5)	0.0013 (5)	−0.0031 (5)
C5	0.0172 (6)	0.0177 (6)	0.0283 (7)	0.0014 (5)	−0.0039 (5)	0.0035 (6)
C6	0.0176 (6)	0.0191 (6)	0.0175 (6)	−0.0013 (5)	−0.0028 (5)	0.0031 (5)
C7	0.0130 (5)	0.0133 (5)	0.0172 (7)	−0.0012 (5)	0.0001 (5)	0.0009 (4)
C8	0.0121 (5)	0.0158 (6)	0.0132 (6)	−0.0023 (4)	0.0002 (4)	−0.0005 (4)
C9	0.0159 (6)	0.0192 (6)	0.0145 (6)	−0.0037 (4)	−0.0014 (5)	0.0018 (5)
C10	0.0160 (6)	0.0253 (7)	0.0135 (6)	−0.0069 (5)	0.0023 (5)	−0.0007 (5)
C11	0.0122 (5)	0.0221 (6)	0.0191 (6)	−0.0032 (4)	0.0018 (5)	−0.0042 (5)
C12	0.0124 (5)	0.0175 (6)	0.0167 (6)	−0.0023 (4)	−0.0003 (4)	−0.0019 (4)
C13	0.0118 (5)	0.0147 (5)	0.0134 (6)	−0.0036 (4)	0.0003 (4)	−0.0009 (4)
C14	0.0107 (5)	0.0152 (5)	0.0128 (5)	−0.0009 (4)	−0.0016 (4)	0.0009 (4)
C15	0.0113 (5)	0.0156 (6)	0.0155 (6)	−0.0019 (4)	−0.0009 (4)	0.0017 (4)
C16	0.0118 (5)	0.0144 (5)	0.0146 (6)	−0.0017 (4)	−0.0030 (4)	0.0027 (4)
C17	0.0157 (6)	0.0212 (6)	0.0181 (7)	−0.0007 (5)	0.0017 (5)	0.0022 (5)
C18	0.0170 (6)	0.0262 (7)	0.0156 (7)	−0.0048 (5)	−0.0008 (5)	0.0072 (5)

Geometric parameters (Å, º) top

S1—C18	1.7164 (16)	C7—C8	1.4823 (18)
S1—C16	1.7217 (13)	C8—C9	1.4011 (18)
O1—C1	1.2140 (17)	C8—C13	1.4075 (18)
O2—C14	1.4041 (14)	C9—C10	1.3927 (19)
O2—H1O2	0.798 (19)	C9—H9A	0.9300
N1—C16	1.3103 (16)	C10—C11	1.3894 (19)
N1—C17	1.3818 (17)	C10—H10A	0.9300
C1—C2	1.4965 (18)	C11—C12	1.3942 (19)
C1—C14	1.5383 (18)	C11—H11A	0.9300
C2—C3	1.3961 (18)	C12—C13	1.3998 (17)
C2—C7	1.4060 (18)	C12—H12A	0.9300
C3—C4	1.393 (2)	C13—C14	1.5232 (17)
C3—H3A	0.9300	C14—C15	1.5605 (17)
C4—C5	1.390 (2)	C15—C16	1.5014 (18)
C4—H4A	0.9300	C15—H15A	0.9700
C5—C6	1.390 (2)	C15—H15B	0.9700
C5—H5A	0.9300	C17—C18	1.3562 (19)
C6—C7	1.4064 (18)	C17—H17A	0.9300
C6—H6A	0.9300	C18—H18A	0.9300

C18—S1—C16	90.30 (7)	C9—C10—H10A	119.9
C14—O2—H1O2	107.7 (13)	C10—C11—C12	119.98 (12)
C16—N1—C17	111.03 (11)	C10—C11—H11A	120.0
O1—C1—C2	123.35 (12)	C12—C11—H11A	120.0
O1—C1—C14	122.59 (12)	C11—C12—C13	120.21 (12)
C2—C1—C14	113.93 (11)	C11—C12—H12A	119.9
C3—C2—C7	121.31 (12)	C13—C12—H12A	119.9
C3—C2—C1	119.04 (12)	C12—C13—C8	120.08 (12)
C7—C2—C1	119.64 (12)	C12—C13—C14	119.90 (11)
C4—C3—C2	119.52 (13)	C8—C13—C14	120.01 (11)
C4—C3—H3A	120.2	O2—C14—C13	113.16 (10)
C2—C3—H3A	120.2	O2—C14—C1	113.02 (10)
C5—C4—C3	119.81 (13)	C13—C14—C1	109.04 (10)
C5—C4—H4A	120.1	O2—C14—C15	104.96 (10)
C3—C4—H4A	120.1	C13—C14—C15	109.78 (10)
C4—C5—C6	120.89 (13)	C1—C14—C15	106.59 (10)
C4—C5—H5A	119.6	C16—C15—C14	112.70 (10)
C6—C5—H5A	119.6	C16—C15—H15A	109.1
C5—C6—C7	120.29 (13)	C14—C15—H15A	109.1
C5—C6—H6A	119.9	C16—C15—H15B	109.1
C7—C6—H6A	119.9	C14—C15—H15B	109.1
C2—C7—C6	118.17 (12)	H15A—C15—H15B	107.8
C2—C7—C8	119.20 (11)	N1—C16—C15	124.01 (11)
C6—C7—C8	122.56 (12)	N1—C16—S1	113.74 (10)
C9—C8—C13	118.81 (12)	C15—C16—S1	122.24 (9)
C9—C8—C7	121.79 (12)	C18—C17—N1	115.57 (12)
C13—C8—C7	119.30 (11)	C18—C17—H17A	122.2
C10—C9—C8	120.78 (13)	N1—C17—H17A	122.2
C10—C9—H9A	119.6	C17—C18—S1	109.36 (11)
C8—C9—H9A	119.6	C17—C18—H18A	125.3
C11—C10—C9	120.11 (12)	S1—C18—H18A	125.3
C11—C10—H10A	119.9

O1—C1—C2—C3	−26.56 (19)	C7—C8—C13—C12	−175.24 (11)
C14—C1—C2—C3	149.37 (11)	C9—C8—C13—C14	−177.89 (11)
O1—C1—C2—C7	154.95 (13)	C7—C8—C13—C14	5.58 (17)
C14—C1—C2—C7	−29.12 (16)	C12—C13—C14—O2	16.31 (16)
C7—C2—C3—C4	1.73 (19)	C8—C13—C14—O2	−164.51 (11)
C1—C2—C3—C4	−176.73 (12)	C12—C13—C14—C1	143.01 (11)
C2—C3—C4—C5	−1.7 (2)	C8—C13—C14—C1	−37.82 (15)
C3—C4—C5—C6	0.7 (2)	C12—C13—C14—C15	−100.57 (13)
C4—C5—C6—C7	0.3 (2)	C8—C13—C14—C15	78.60 (14)
C3—C2—C7—C6	−0.76 (19)	O1—C1—C14—O2	−8.85 (17)
C1—C2—C7—C6	177.69 (11)	C2—C1—C14—O2	175.19 (10)
C3—C2—C7—C8	176.32 (11)	O1—C1—C14—C13	−135.62 (13)
C1—C2—C7—C8	−5.23 (18)	C2—C1—C14—C13	48.41 (13)
C5—C6—C7—C2	−0.27 (19)	O1—C1—C14—C15	105.94 (13)
C5—C6—C7—C8	−177.25 (12)	C2—C1—C14—C15	−70.03 (13)
C2—C7—C8—C9	−158.44 (12)	O2—C14—C15—C16	64.01 (13)
C6—C7—C8—C9	18.51 (19)	C13—C14—C15—C16	−174.07 (10)
C2—C7—C8—C13	17.98 (18)	C1—C14—C15—C16	−56.11 (13)
C6—C7—C8—C13	−165.07 (12)	C17—N1—C16—C15	177.95 (12)
C13—C8—C9—C10	−1.71 (19)	C17—N1—C16—S1	−0.74 (14)
C7—C8—C9—C10	174.73 (12)	C14—C15—C16—N1	120.47 (13)
C8—C9—C10—C11	0.73 (19)	C14—C15—C16—S1	−60.94 (14)
C9—C10—C11—C12	0.69 (19)	C18—S1—C16—N1	0.76 (11)
C10—C11—C12—C13	−1.11 (19)	C18—S1—C16—C15	−177.96 (11)
C11—C12—C13—C8	0.11 (19)	C16—N1—C17—C18	0.32 (17)
C11—C12—C13—C14	179.28 (11)	N1—C17—C18—S1	0.25 (16)
C9—C8—C13—C12	1.28 (18)	C16—S1—C18—C17	−0.54 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of C8–C13 and C2–C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1ⁱ	0.80 (2)	1.976 (19)	2.7542 (14)	165 (2)
C5—H5A···Cg1ⁱⁱ	0.93	2.83	3.6508 (16)	147
C12—H12A···Cg2ⁱⁱⁱ	0.93	2.85	3.7214 (15)	156
C18—H18A···Cg1^iv	0.93	2.72	3.3301 (16)	124

Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) −x−1/2, y+5/2, z+1/2; (iii) −x+1/2, y+3/2, z+1/2; (iv) −x+1, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃NO₂S
M_r	307.35
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	12.5623 (17), 7.3222 (10), 15.462 (2)
V (Å³)	1422.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.33 × 0.17 × 0.17

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.926, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	14577, 3814, 3635
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.074, 1.03
No. of reflections	3814
No. of parameters	203
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.21
Absolute structure	Flack (1983), 1674 Friedel pairs
Absolute structure parameter	0.04 (5)

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of C8–C13 and C2–C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1ⁱ	0.80 (2)	1.976 (19)	2.7542 (14)	165 (2)
C5—H5A···Cg1ⁱⁱ	0.93	2.83	3.6508 (16)	147
C12—H12A···Cg2ⁱⁱⁱ	0.93	2.85	3.7214 (15)	156
C18—H18A···Cg1^iv	0.93	2.72	3.3301 (16)	124

Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) −x−1/2, y+5/2, z+1/2; (iii) −x+1/2, y+3/2, z+1/2; (iv) −x+1, −y+1, z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7576-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). Financial support from the National Science Foundation of China (20702024) is acknowledged. JHG also thanks USM for the award of a USM fellowship.

References

Bloom, S. M. (1961). J. Am. Chem. Soc. 38, 3808–3812. CrossRef Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jones, P. G., Kirby, A. J. & Pilkington, M. (2002). Acta Cryst. E58, o268–o269. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kumagai, Y., Arimoto, T., Shinyashiki, M., Shimojo, N., Nakai, Y., Yoshikawa, T. & Sa-Gai, M. (1997). Free Radical Biol. Med. 33, 479–487. CrossRef Web of Science Google Scholar
Li, X.-M., Wang, L., Xu, J.-H., Zhang, S.-S. & Fun, H.-K. (2003). Acta Cryst. E59, o1907–o1908. Web of Science CSD CrossRef IUCr Journals Google Scholar
McClellan, R. O. (1987). Annu. Rev. Pharmacol. Toxicol. 27, 279–300. CrossRef CAS PubMed Web of Science Google Scholar
Meyer, R. & Spengler, O. (1905). Ber. Dtsch. Chem. Ges. 38, 440–450. CrossRef CAS Google Scholar
Milko, P. & Roithova, J. (2009). Inorg. Chem. 48, 11734–11742. Web of Science CrossRef PubMed CAS Google Scholar
Mustafa, A., Harhash, A. H. E., Mansour, A. K. E. & Omran, S. M. A. E. (1956). J. Am. Chem. Soc. 78, 4306–4309. CrossRef CAS Web of Science Google Scholar
Nel, A. E., Diaz-Sanchez, D. & Li, N. (2001). Curr. Opin. Pulm. Med. 7, 20–26. CrossRef PubMed CAS Google Scholar
Schuetzle, D., Lee, F. S.-C. & Prater, T. J. (1981). Int. J. Environ. Anal. Chem. 9, 93–144. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shimada, H., Oginuma, M., Hara, A. & Imamura, Y. (2004). Chem. Rev. Toxicol. 17, 1145–1150. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, Y.-F., Cui, Y.-P., Li, J.-K. & Zheng, Z.-B. (2007). Acta Cryst. E63, o1751–o1752. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, L., Usman, A., Fun, H.-K., Zhang, Y. & Xu, J.-H. (2003). Acta Cryst. E59, o721–o722. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, Y., Wang, L., Zhang, M., Fun, H.-K. & Xu, J.-X. (2004). Org. Lett. 4, 4893–4895. Web of Science CSD CrossRef Google Scholar

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Volume 66| Part 7| July 2010| Pages o1683-o1684

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