10-Hy-droxy-10-(1,3-thia-zol-2-ylmeth-yl)phenanthren-9(10H)-one.

In the title phenanthrenone compound, C(18)H(13)NO(2)S, the dihydro-phenanthrene ring system is not planar, with its central ring distorted to a screw-boat conformation. The essentially planar thia-zole ring [maximum deviation = 0.005 (1) Å] is inclined at an inter-planar angle of 23.36 (5)° with respect to the mean plane through the dihydro-phenanthrene ring system. In the crystal packing, inter-molecular O-H⋯N hydrogen bonds link the mol-ecules into infinite chains along the a axis. Weak inter-molecular C-H⋯π inter-actions 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 = 307.35

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.074

S = 1.03

3814 reflections

203 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1674 Friedel pairs

Flack parameter: 0.04 (5)

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022439/wn2393sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H13NO2S	F(000) = 640
Mr = 307.35	Dx = 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

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

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(Fo2) + (0.0445P)2 + 0.2177P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3814 reflections	Δρmax = 0.32 e Å−3
203 parameters	Δρmin = −0.21 e Å−3
1 restraint	Absolute structure: Flack (1983), 1674 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (5)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···Cg1iv	0.93	2.72	3.3301 (16)	124

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⋯Cg1iv	0.93	2.72	3.3301 (16)	124

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .