10-(2-Eth-oxy-1,3-thia-zol-5-yl)-10-hy-droxy-phenanthren-9(10H)-one.

In the title compound, C(19)H(15)NO(3)S, the dihydro-phenanthrene unit is not planar, its central ring being distorted towards a sofa conformation. The essentially planar thia-zole 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 dihydro-phenanthrene unit. In the crystal structure, pairs of inter-molecular C-H⋯O hydrogen bonds link adjacent mol-ecules into inversion dimers. Inter-molecular O-H⋯N hydrogen bonds further inter-connect these dimers into chains along the a axis. The crystal structure is further stabilized by weak inter-molecular C-H⋯π inter-actions involving the thia-zole 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 = 337.38

Triclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.139

S = 1.12

4157 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.96 e Å−3

Δρmin = −0.51 e Å−3

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/S1600536810031004/bt5320sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031004/bt5320Isup2.hkl

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

C19H15NO3S	Z = 2
Mr = 337.38	F(000) = 352
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.086P)2 + 0.3384P] where P = (Fo2 + 2Fc2)/3
4157 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.96 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

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	−0.03580 (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)*

	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)

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)

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

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) ; (ii) ; (iii) .