3-Hy-droxy-2-[(2-hy-droxy-4,4-dimethyl-6-oxocyclo-hex-1-en-1-yl)(3-nitro-phen-yl)meth-yl]-5,5-dimethyl-cyclo-hex-2-en-1-one.

Each of the cyclohexenone rings in the title compound, C(23)H(27)NO(6), adopts a half-chair (envelope) conformation with the C atom carrying the methyl groups lying out of the plane defined by the five remaining C atoms; the O atoms lie to the same side of the mol-ecule as the respective >C(CH(3))(2) atoms. The hy-droxy and carbonyl O atoms face each other and are orientated to allow for the formation of two intra-molecular O-H⋯O hydrogen bonds. In the crystal, the presence of C-H⋯O contacts leads to the formation of supra-molecular chains along the b axis. These aggregate into layers that stack along c.

Related literature

For the biological activity and uses of xanthenes, see: Jonathan et al. (1988 ▶); Pohlers & Scaiano (1997 ▶); Hilderbrand & Weissleder (2007 ▶). For background to xanthenedione derivatives, see: Hatakeyama et al. (1988 ▶); Shchekotikhin & Nikolaeva (2006 ▶).

Experimental

Crystal data

C23H27NO6

M = 413.46

Monoclinic,

a = 14.2326 (10) Å

b = 8.6505 (6) Å

c = 16.8410 (12) Å

β = 97.796 (1)°

V = 2054.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.792, T max = 0.862

18883 measured reflections

4717 independent reflections

3928 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.03

4717 reflections

279 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040079/hb5662sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040079/hb5662Isup2.hkl

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

C23H27NO6	F(000) = 880
Mr = 413.46	Dx = 1.337 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5854 reflections
a = 14.2326 (10) Å	θ = 4.5–28.2°
b = 8.6505 (6) Å	µ = 0.10 mm−1
c = 16.8410 (12) Å	T = 100 K
β = 97.796 (1)°	Block, colourless
V = 2054.3 (3) Å3	0.30 × 0.30 × 0.20 mm
Z = 4

Bruker SMART APEX CCD diffractometer	4717 independent reflections
Radiation source: fine-focus sealed tube	3928 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→18
Tmin = 0.792, Tmax = 0.862	k = −11→11
18883 measured reflections	l = −21→21

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0605P)2 + 0.67P] where P = (Fo2 + 2Fc2)/3
4717 reflections	(Δ/σ)max = 0.001
279 parameters	Δρmax = 0.37 e Å−3
2 restraints	Δρmin = −0.23 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O1	0.65593 (7)	0.65589 (10)	0.67564 (5)	0.0159 (2)
H1o	0.6569 (15)	0.594 (2)	0.6365 (9)	0.048 (6)*
O2	0.73862 (7)	1.02234 (10)	0.49100 (5)	0.0170 (2)
O3	0.73479 (7)	0.82683 (11)	0.37346 (5)	0.0170 (2)
H3o	0.7407 (13)	0.8846 (19)	0.4154 (8)	0.036 (5)*
O4	0.63116 (6)	0.46796 (10)	0.55110 (5)	0.0163 (2)
O5	0.99653 (7)	0.53999 (12)	0.35663 (6)	0.0237 (2)
O6	1.13360 (7)	0.63202 (12)	0.40630 (6)	0.0259 (2)
N1	1.04746 (8)	0.61823 (13)	0.40582 (7)	0.0176 (2)
C1	0.71426 (9)	0.83167 (14)	0.58531 (7)	0.0129 (2)
C2	0.67059 (9)	0.79995 (14)	0.65085 (7)	0.0134 (2)
C3	0.63844 (9)	0.92120 (14)	0.70461 (7)	0.0153 (3)
H3A	0.6898	0.9405	0.7493	0.018*
H3B	0.5829	0.8817	0.7279	0.018*
C4	0.61160 (9)	1.07463 (14)	0.66175 (7)	0.0149 (3)
C5	0.69030 (10)	1.11682 (15)	0.61177 (8)	0.0184 (3)
H5A	0.6701	1.2088	0.5788	0.022*
H5B	0.7480	1.1453	0.6486	0.022*
C6	0.71497 (9)	0.98965 (15)	0.55741 (8)	0.0145 (3)
C7	0.51615 (10)	1.05773 (17)	0.60799 (8)	0.0217 (3)
H7A	0.4669	1.0306	0.6409	0.032*
H7B	0.5209	0.9761	0.5684	0.032*
H7C	0.4997	1.1557	0.5803	0.032*
C8	0.60339 (10)	1.20199 (15)	0.72332 (8)	0.0187 (3)
H8A	0.5531	1.1754	0.7554	0.028*
H8B	0.5880	1.3002	0.6955	0.028*
H8C	0.6638	1.2121	0.7585	0.028*
C9	0.76179 (8)	0.70610 (14)	0.54208 (7)	0.0124 (2)
H9	0.7692	0.6185	0.5812	0.015*
C10	0.70261 (9)	0.63781 (14)	0.46833 (7)	0.0129 (2)
C11	0.69851 (9)	0.69205 (14)	0.39210 (8)	0.0139 (3)
C12	0.65447 (9)	0.60340 (15)	0.31987 (8)	0.0162 (3)
H12A	0.6947	0.6153	0.2767	0.019*
H12B	0.5916	0.6487	0.3006	0.019*
C13	0.64204 (9)	0.43071 (15)	0.33584 (8)	0.0162 (3)
C14	0.59406 (10)	0.41744 (16)	0.41182 (8)	0.0189 (3)
H14A	0.5281	0.4556	0.3999	0.023*
H14B	0.5913	0.3070	0.4268	0.023*
C15	0.64394 (9)	0.50637 (14)	0.48217 (7)	0.0140 (2)
C16	0.57961 (10)	0.35702 (17)	0.26472 (8)	0.0228 (3)
H16A	0.5718	0.2467	0.2752	0.034*
H16B	0.6097	0.3698	0.2161	0.034*
H16C	0.5174	0.4074	0.2573	0.034*
C17	0.73790 (10)	0.34775 (15)	0.34742 (8)	0.0201 (3)
H17A	0.7282	0.2378	0.3577	0.030*
H17B	0.7786	0.3932	0.3931	0.030*
H17C	0.7683	0.3592	0.2989	0.030*
C18	0.86411 (8)	0.74648 (14)	0.53038 (7)	0.0130 (2)
C19	0.91956 (9)	0.84390 (15)	0.58406 (8)	0.0156 (3)
H19	0.8912	0.8949	0.6248	0.019*
C20	1.01514 (9)	0.86788 (15)	0.57927 (8)	0.0175 (3)
H20	1.0509	0.9350	0.6165	0.021*
C21	1.05918 (9)	0.79508 (15)	0.52075 (8)	0.0171 (3)
H21	1.1245	0.8105	0.5170	0.021*
C22	1.00352 (9)	0.69910 (15)	0.46819 (7)	0.0150 (3)
C23	0.90774 (9)	0.67322 (14)	0.47154 (7)	0.0144 (3)
H23	0.8724	0.6062	0.4340	0.017*

	U11	U22	U33	U12	U13	U23
O1	0.0196 (5)	0.0135 (4)	0.0154 (4)	−0.0009 (4)	0.0058 (4)	0.0015 (3)
O2	0.0193 (5)	0.0155 (5)	0.0174 (4)	−0.0004 (4)	0.0067 (4)	0.0025 (3)
O3	0.0208 (5)	0.0146 (4)	0.0161 (5)	−0.0015 (4)	0.0048 (4)	0.0019 (4)
O4	0.0186 (5)	0.0138 (4)	0.0176 (4)	−0.0009 (3)	0.0067 (4)	0.0010 (3)
O5	0.0225 (5)	0.0281 (5)	0.0216 (5)	0.0016 (4)	0.0070 (4)	−0.0041 (4)
O6	0.0152 (5)	0.0308 (6)	0.0342 (6)	0.0022 (4)	0.0126 (4)	0.0012 (5)
N1	0.0169 (6)	0.0171 (5)	0.0204 (6)	0.0040 (4)	0.0078 (4)	0.0052 (4)
C1	0.0115 (6)	0.0124 (6)	0.0151 (6)	0.0015 (4)	0.0027 (5)	0.0000 (4)
C2	0.0113 (6)	0.0141 (6)	0.0146 (6)	0.0008 (5)	0.0012 (4)	0.0017 (5)
C3	0.0167 (6)	0.0159 (6)	0.0140 (6)	0.0006 (5)	0.0048 (5)	−0.0002 (5)
C4	0.0151 (6)	0.0155 (6)	0.0142 (6)	0.0017 (5)	0.0029 (5)	−0.0015 (5)
C5	0.0225 (7)	0.0127 (6)	0.0216 (6)	0.0015 (5)	0.0091 (5)	0.0001 (5)
C6	0.0113 (6)	0.0149 (6)	0.0176 (6)	0.0000 (5)	0.0035 (5)	0.0001 (5)
C7	0.0183 (7)	0.0257 (7)	0.0201 (7)	0.0054 (5)	−0.0003 (5)	−0.0049 (5)
C8	0.0190 (6)	0.0175 (6)	0.0198 (6)	0.0019 (5)	0.0042 (5)	−0.0034 (5)
C9	0.0123 (6)	0.0120 (6)	0.0134 (6)	0.0007 (4)	0.0036 (4)	0.0010 (4)
C10	0.0106 (5)	0.0126 (6)	0.0158 (6)	0.0013 (5)	0.0029 (5)	−0.0004 (5)
C11	0.0110 (6)	0.0130 (6)	0.0183 (6)	0.0019 (4)	0.0045 (5)	0.0010 (5)
C12	0.0159 (6)	0.0179 (6)	0.0149 (6)	0.0005 (5)	0.0021 (5)	0.0010 (5)
C13	0.0161 (6)	0.0173 (6)	0.0153 (6)	−0.0027 (5)	0.0028 (5)	−0.0012 (5)
C14	0.0181 (6)	0.0199 (7)	0.0194 (6)	−0.0062 (5)	0.0051 (5)	−0.0017 (5)
C15	0.0120 (6)	0.0133 (6)	0.0173 (6)	0.0029 (5)	0.0042 (5)	0.0002 (5)
C16	0.0231 (7)	0.0258 (7)	0.0191 (7)	−0.0059 (6)	0.0012 (5)	−0.0037 (6)
C17	0.0226 (7)	0.0164 (6)	0.0214 (7)	0.0025 (5)	0.0034 (5)	−0.0026 (5)
C18	0.0118 (6)	0.0134 (6)	0.0145 (6)	0.0019 (5)	0.0036 (5)	0.0047 (4)
C19	0.0167 (6)	0.0157 (6)	0.0145 (6)	0.0018 (5)	0.0028 (5)	0.0015 (5)
C20	0.0162 (6)	0.0170 (6)	0.0185 (6)	−0.0020 (5)	−0.0005 (5)	0.0020 (5)
C21	0.0131 (6)	0.0175 (6)	0.0209 (6)	0.0007 (5)	0.0030 (5)	0.0059 (5)
C22	0.0142 (6)	0.0145 (6)	0.0173 (6)	0.0039 (5)	0.0058 (5)	0.0049 (5)
C23	0.0145 (6)	0.0138 (6)	0.0152 (6)	0.0005 (5)	0.0030 (5)	0.0023 (5)

O1—C2	1.3395 (15)	C9—H9	1.0000
O1—H1o	0.851 (9)	C10—C11	1.3607 (17)
O2—C6	1.2436 (15)	C10—C15	1.4481 (17)
O3—C11	1.3299 (15)	C11—C12	1.5014 (18)
O3—H3o	0.860 (9)	C12—C13	1.5323 (18)
O4—C15	1.2443 (15)	C12—H12A	0.9900
O5—N1	1.2275 (15)	C12—H12B	0.9900
O6—N1	1.2308 (14)	C13—C17	1.5304 (18)
N1—C22	1.4704 (16)	C13—C16	1.5303 (18)
C1—C2	1.3662 (17)	C13—C14	1.5343 (18)
C1—C6	1.4456 (17)	C14—C15	1.5072 (18)
C1—C9	1.5169 (16)	C14—H14A	0.9900
C2—C3	1.4971 (17)	C14—H14B	0.9900
C3—C4	1.5341 (17)	C16—H16A	0.9800
C3—H3A	0.9900	C16—H16B	0.9800
C3—H3B	0.9900	C16—H16C	0.9800
C4—C8	1.5282 (17)	C17—H17A	0.9800
C4—C5	1.5337 (18)	C17—H17B	0.9800
C4—C7	1.5340 (18)	C17—H17C	0.9800
C5—C6	1.5029 (17)	C18—C23	1.3913 (17)
C5—H5A	0.9900	C18—C19	1.3988 (18)
C5—H5B	0.9900	C19—C20	1.3893 (18)
C7—H7A	0.9800	C19—H19	0.9500
C7—H7B	0.9800	C20—C21	1.3886 (19)
C7—H7C	0.9800	C20—H20	0.9500
C8—H8A	0.9800	C21—C22	1.3821 (19)
C8—H8B	0.9800	C21—H21	0.9500
C8—H8C	0.9800	C22—C23	1.3902 (18)
C9—C10	1.5223 (17)	C23—H23	0.9500
C9—C18	1.5360 (16)
C2—O1—H1o	109.0 (14)	O3—C11—C12	112.91 (11)
C11—O3—H3o	108.3 (13)	C10—C11—C12	123.24 (11)
O6—N1—O5	123.66 (11)	C11—C12—C13	113.65 (10)
O6—N1—C22	117.97 (11)	C11—C12—H12A	108.8
O5—N1—C22	118.36 (11)	C13—C12—H12A	108.8
C2—C1—C6	118.45 (11)	C11—C12—H12B	108.8
C2—C1—C9	121.69 (11)	C13—C12—H12B	108.8
C6—C1—C9	119.85 (11)	H12A—C12—H12B	107.7
O1—C2—C1	123.08 (11)	C17—C13—C16	108.50 (11)
O1—C2—C3	112.96 (10)	C17—C13—C12	110.94 (11)
C1—C2—C3	123.90 (11)	C16—C13—C12	109.71 (11)
C2—C3—C4	113.50 (10)	C17—C13—C14	110.40 (11)
C2—C3—H3A	108.9	C16—C13—C14	110.16 (11)
C4—C3—H3A	108.9	C12—C13—C14	107.12 (11)
C2—C3—H3B	108.9	C15—C14—C13	113.70 (11)
C4—C3—H3B	108.9	C15—C14—H14A	108.8
H3A—C3—H3B	107.7	C13—C14—H14A	108.8
C8—C4—C5	109.24 (11)	C15—C14—H14B	108.8
C8—C4—C7	109.03 (11)	C13—C14—H14B	108.8
C5—C4—C7	110.68 (11)	H14A—C14—H14B	107.7
C8—C4—C3	109.97 (10)	O4—C15—C10	121.35 (12)
C5—C4—C3	108.08 (10)	O4—C15—C14	118.96 (11)
C7—C4—C3	109.83 (11)	C10—C15—C14	119.65 (11)
C6—C5—C4	114.11 (11)	C13—C16—H16A	109.5
C6—C5—H5A	108.7	C13—C16—H16B	109.5
C4—C5—H5A	108.7	H16A—C16—H16B	109.5
C6—C5—H5B	108.7	C13—C16—H16C	109.5
C4—C5—H5B	108.7	H16A—C16—H16C	109.5
H5A—C5—H5B	107.6	H16B—C16—H16C	109.5
O2—C6—C1	121.46 (12)	C13—C17—H17A	109.5
O2—C6—C5	119.71 (11)	C13—C17—H17B	109.5
C1—C6—C5	118.79 (11)	H17A—C17—H17B	109.5
C4—C7—H7A	109.5	C13—C17—H17C	109.5
C4—C7—H7B	109.5	H17A—C17—H17C	109.5
H7A—C7—H7B	109.5	H17B—C17—H17C	109.5
C4—C7—H7C	109.5	C23—C18—C19	117.87 (11)
H7A—C7—H7C	109.5	C23—C18—C9	120.68 (11)
H7B—C7—H7C	109.5	C19—C18—C9	121.04 (11)
C4—C8—H8A	109.5	C20—C19—C18	121.57 (12)
C4—C8—H8B	109.5	C20—C19—H19	119.2
H8A—C8—H8B	109.5	C18—C19—H19	119.2
C4—C8—H8C	109.5	C19—C20—C21	120.88 (12)
H8A—C8—H8C	109.5	C19—C20—H20	119.6
H8B—C8—H8C	109.5	C21—C20—H20	119.6
C1—C9—C10	115.85 (10)	C22—C21—C20	116.90 (12)
C1—C9—C18	113.02 (10)	C22—C21—H21	121.6
C10—C9—C18	114.39 (10)	C20—C21—H21	121.6
C1—C9—H9	103.9	C21—C22—C23	123.42 (12)
C10—C9—H9	103.9	C21—C22—N1	118.75 (11)
C18—C9—H9	103.9	C23—C22—N1	117.83 (11)
C11—C10—C15	118.08 (11)	C22—C23—C18	119.37 (12)
C11—C10—C9	125.74 (11)	C22—C23—H23	120.3
C15—C10—C9	116.15 (10)	C18—C23—H23	120.3
O3—C11—C10	123.83 (12)
C6—C1—C2—O1	171.69 (11)	C10—C11—C12—C13	−17.54 (17)
C9—C1—C2—O1	−8.61 (19)	C11—C12—C13—C17	−71.32 (14)
C6—C1—C2—C3	−11.38 (18)	C11—C12—C13—C16	168.81 (11)
C9—C1—C2—C3	168.32 (11)	C11—C12—C13—C14	49.24 (14)
O1—C2—C3—C4	−153.63 (11)	C17—C13—C14—C15	68.28 (14)
C1—C2—C3—C4	29.16 (17)	C16—C13—C14—C15	−171.90 (11)
C2—C3—C4—C8	−166.16 (11)	C12—C13—C14—C15	−52.62 (14)
C2—C3—C4—C5	−46.99 (14)	C11—C10—C15—O4	−167.09 (11)
C2—C3—C4—C7	73.84 (14)	C9—C10—C15—O4	11.17 (17)
C8—C4—C5—C6	171.38 (11)	C11—C10—C15—C14	10.51 (18)
C7—C4—C5—C6	−68.56 (14)	C9—C10—C15—C14	−171.23 (11)
C3—C4—C5—C6	51.74 (14)	C13—C14—C15—O4	−157.72 (12)
C2—C1—C6—O2	−167.47 (12)	C13—C14—C15—C10	24.63 (17)
C9—C1—C6—O2	12.83 (18)	C1—C9—C18—C23	−159.11 (11)
C2—C1—C6—C5	15.06 (18)	C10—C9—C18—C23	−23.66 (16)
C9—C1—C6—C5	−164.65 (11)	C1—C9—C18—C19	28.36 (16)
C4—C5—C6—O2	145.36 (12)	C10—C9—C18—C19	163.81 (11)
C4—C5—C6—C1	−37.13 (16)	C23—C18—C19—C20	0.13 (18)
C2—C1—C9—C10	96.76 (14)	C9—C18—C19—C20	172.86 (11)
C6—C1—C9—C10	−83.54 (14)	C18—C19—C20—C21	−0.2 (2)
C2—C1—C9—C18	−128.46 (12)	C19—C20—C21—C22	0.12 (19)
C6—C1—C9—C18	51.23 (15)	C20—C21—C22—C23	−0.03 (19)
C1—C9—C10—C11	88.93 (15)	C20—C21—C22—N1	−179.31 (11)
C18—C9—C10—C11	−45.23 (16)	O6—N1—C22—C21	4.50 (17)
C1—C9—C10—C15	−89.18 (13)	O5—N1—C22—C21	−176.02 (11)
C18—C9—C10—C15	136.66 (11)	O6—N1—C22—C23	−174.82 (11)
C15—C10—C11—O3	167.35 (11)	O5—N1—C22—C23	4.65 (17)
C9—C10—C11—O3	−10.7 (2)	C21—C22—C23—C18	−0.02 (19)
C15—C10—C11—C12	−14.28 (18)	N1—C22—C23—C18	179.27 (11)
C9—C10—C11—C12	167.64 (11)	C19—C18—C23—C22	−0.03 (18)
O3—C11—C12—C13	160.99 (11)	C9—C18—C23—C22	−172.79 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O4	0.85 (1)	1.80 (1)	2.6392 (13)	167 (2)
O3—H3o···O2	0.86 (1)	1.75 (1)	2.5985 (13)	170 (2)
C5—H5a···O4i	0.99	2.34	3.2781 (16)	158
C9—H9···O6ii	1.00	2.56	3.3431 (16)	135
C21—H21···O2iii	0.95	2.44	3.3121 (16)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O4	0.85 (1)	1.80 (1)	2.6392 (13)	167 (2)
O3—H3o⋯O2	0.86 (1)	1.75 (1)	2.5985 (13)	170 (2)
C5—H5a⋯O4i	0.99	2.34	3.2781 (16)	158
C9—H9⋯O6ii	1.00	2.56	3.3431 (16)	135
C21—H21⋯O2iii	0.95	2.44	3.3121 (16)	152

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