3,3,6,6-Tetra-methyl-9-(2-nitro-phen-yl)-3,4,6,7-tetra-hydro-2H-xanthene-1,8(5H,9H)-dione.

In the title compound, C(23)H(25)NO(5), the pyran ring adopts a flattened boat conformation, while the two cyclo-hexenone rings are in envelope conformations. The 3-nitro-phenyl ring is almost perpendicular to the pyran ring, making a dihedral angle of 87.1 (3)°.

Related literature

For the use of xanthenes as dyes and fluorescent materials for visualization of biomolecules and in laser technologies, see: Menchen et al. (2003 ▶); Banerjee & Mukherjee (1981 ▶). They can be converted by oxidation into xanthylium salts, which are also effective as dyes and fluorescent materials, see: Nogradi (2003 ▶); Kamel & Shoeb (1964 ▶). For the biological and pharmaceutical properties of xanthenes, see: Hideo (1981 ▶); Lambert et al. (1997 ▶); Poupelin et al. (1978 ▶).

Experimental

Crystal data

C23H25NO5

M = 395.44

Orthorhombic,

a = 12.199 (2) Å

b = 10.510 (2) Å

c = 32.484 (7) Å

V = 4164.9 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.20 × 0.16 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2002 ▶) T min = 0.983, T max = 0.991

21559 measured reflections

3670 independent reflections

3242 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.144

S = 1.16

3670 reflections

267 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, publication_text. DOI: 10.1107/S1600536810029211/jh2186sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029211/jh2186Isup2.hkl

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

C23H25NO5	Dx = 1.261 Mg m−3
Mr = 395.44	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9106 reflections
a = 12.199 (2) Å	θ = 1.9–28.1°
b = 10.510 (2) Å	µ = 0.09 mm−1
c = 32.484 (7) Å	T = 113 K
V = 4164.9 (14) Å3	Prism, white
Z = 8	0.20 × 0.16 × 0.10 mm
F(000) = 1680

Rigaku Saturn CCD area-detector diffractometer	3670 independent reflections
Radiation source: rotating anode	3242 reflections with I > 2σ(I)
confocal	Rint = 0.053
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 2.5°
ω and φ scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)	k = −10→12
Tmin = 0.983, Tmax = 0.991	l = −38→36
21559 measured reflections

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)] = 0.063	H-atom parameters constrained
wR(F2) = 0.144	w = 1/[σ2(Fo2) + (0.0574P)2 + 1.5964P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max = 0.001
3670 reflections	Δρmax = 0.22 e Å−3
267 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0098 (8)

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	0.54601 (12)	0.17933 (14)	0.36579 (4)	0.0237 (4)
O2	0.25719 (14)	0.45727 (16)	0.40103 (5)	0.0387 (5)
O3	0.49229 (13)	0.50696 (15)	0.26800 (4)	0.0306 (4)
O4	0.77268 (15)	0.56112 (18)	0.42780 (6)	0.0474 (5)
O5	0.78206 (14)	0.76618 (17)	0.42061 (5)	0.0400 (5)
N1	0.73522 (16)	0.66330 (19)	0.41615 (5)	0.0299 (5)
C1	0.56412 (18)	0.2415 (2)	0.32907 (6)	0.0219 (5)
C2	0.64378 (18)	0.1708 (2)	0.30297 (6)	0.0227 (5)
H2A	0.6054	0.0996	0.2892	0.027*
H2B	0.7015	0.1340	0.3208	0.027*
C3	0.69762 (18)	0.2553 (2)	0.27026 (6)	0.0226 (5)
C4	0.60627 (18)	0.3304 (2)	0.24887 (6)	0.0246 (5)
H4A	0.6398	0.3897	0.2288	0.029*
H4B	0.5596	0.2702	0.2333	0.029*
C5	0.53483 (18)	0.4053 (2)	0.27790 (6)	0.0244 (5)
C6	0.51360 (17)	0.3502 (2)	0.31886 (6)	0.0214 (5)
C7	0.43583 (17)	0.4193 (2)	0.34753 (6)	0.0230 (5)
H7	0.3668	0.4380	0.3321	0.028*
C8	0.40825 (17)	0.3317 (2)	0.38289 (6)	0.0238 (5)
C9	0.31381 (19)	0.3637 (2)	0.40908 (7)	0.0296 (5)
C10	0.2868 (2)	0.2742 (2)	0.44399 (7)	0.0343 (6)
H10A	0.2361	0.2078	0.4337	0.041*
H10B	0.2481	0.3224	0.4658	0.041*
C11	0.3870 (2)	0.2095 (2)	0.46289 (6)	0.0298 (6)
C12	0.44987 (19)	0.1422 (2)	0.42801 (6)	0.0261 (5)
H12A	0.5227	0.1156	0.4383	0.031*
H12B	0.4094	0.0647	0.4198	0.031*
C13	0.46462 (17)	0.2256 (2)	0.39124 (6)	0.0227 (5)
C14	0.75809 (19)	0.1729 (2)	0.23874 (6)	0.0278 (5)
H14A	0.8182	0.1276	0.2524	0.042*
H14B	0.7878	0.2272	0.2169	0.042*
H14C	0.7070	0.1112	0.2268	0.042*
C15	0.78024 (19)	0.3455 (2)	0.29057 (7)	0.0295 (5)
H15A	0.8387	0.2957	0.3035	0.044*
H15B	0.7429	0.3968	0.3115	0.044*
H15C	0.8119	0.4017	0.2696	0.044*
C16	0.4605 (2)	0.3084 (2)	0.48427 (7)	0.0421 (7)
H16A	0.4185	0.3519	0.5058	0.063*
H16B	0.4859	0.3708	0.4640	0.063*
H16C	0.5238	0.2656	0.4966	0.063*
C17	0.3501 (2)	0.1099 (2)	0.49439 (7)	0.0395 (7)
H17A	0.3046	0.0458	0.4807	0.059*
H17B	0.3075	0.1514	0.5161	0.059*
H17C	0.4146	0.0687	0.5065	0.059*
C18	0.48347 (18)	0.5456 (2)	0.36303 (6)	0.0237 (5)
C19	0.42695 (19)	0.6595 (2)	0.35885 (6)	0.0281 (5)
H19	0.3565	0.6592	0.3464	0.034*
C20	0.4708 (2)	0.7741 (2)	0.37241 (7)	0.0318 (6)
H20	0.4305	0.8507	0.3689	0.038*
C21	0.57294 (19)	0.7774 (2)	0.39100 (6)	0.0296 (5)
H21	0.6043	0.8551	0.4002	0.035*
C22	0.62764 (18)	0.6625 (2)	0.39566 (6)	0.0250 (5)
C23	0.58551 (18)	0.5471 (2)	0.38256 (6)	0.0241 (5)
H23	0.6252	0.4704	0.3868	0.029*

	U11	U22	U33	U12	U13	U23
O1	0.0265 (9)	0.0227 (9)	0.0221 (7)	0.0030 (7)	0.0026 (6)	0.0018 (6)
O2	0.0319 (10)	0.0312 (10)	0.0529 (10)	0.0085 (8)	0.0103 (8)	0.0031 (8)
O3	0.0332 (10)	0.0266 (10)	0.0319 (8)	0.0075 (8)	−0.0029 (7)	0.0042 (7)
O4	0.0405 (12)	0.0360 (12)	0.0655 (12)	−0.0072 (9)	−0.0202 (9)	0.0157 (9)
O5	0.0310 (10)	0.0320 (11)	0.0572 (11)	−0.0071 (8)	0.0037 (8)	−0.0187 (8)
N1	0.0283 (11)	0.0318 (12)	0.0297 (10)	−0.0046 (10)	0.0018 (8)	−0.0044 (8)
C1	0.0237 (12)	0.0211 (12)	0.0209 (10)	−0.0029 (10)	−0.0028 (8)	−0.0011 (8)
C2	0.0260 (12)	0.0187 (12)	0.0232 (10)	0.0014 (10)	−0.0016 (8)	−0.0011 (8)
C3	0.0248 (12)	0.0183 (12)	0.0246 (10)	−0.0003 (10)	0.0008 (8)	−0.0002 (8)
C4	0.0275 (12)	0.0234 (12)	0.0228 (10)	0.0001 (10)	0.0001 (9)	0.0000 (9)
C5	0.0220 (12)	0.0227 (13)	0.0286 (11)	−0.0012 (10)	−0.0045 (9)	−0.0003 (9)
C6	0.0214 (12)	0.0191 (12)	0.0236 (10)	−0.0002 (9)	−0.0016 (8)	−0.0018 (8)
C7	0.0198 (11)	0.0230 (12)	0.0261 (11)	0.0015 (10)	−0.0030 (8)	−0.0012 (9)
C8	0.0229 (12)	0.0224 (12)	0.0262 (10)	−0.0018 (10)	−0.0014 (9)	−0.0016 (9)
C9	0.0277 (13)	0.0249 (13)	0.0362 (12)	−0.0018 (11)	0.0035 (10)	−0.0045 (10)
C10	0.0342 (14)	0.0283 (14)	0.0403 (13)	−0.0020 (12)	0.0134 (10)	−0.0021 (10)
C11	0.0347 (14)	0.0253 (13)	0.0293 (11)	−0.0053 (11)	0.0079 (10)	−0.0030 (10)
C12	0.0272 (12)	0.0237 (13)	0.0273 (11)	−0.0023 (10)	0.0032 (9)	0.0004 (9)
C13	0.0194 (11)	0.0232 (13)	0.0253 (10)	−0.0035 (10)	0.0016 (8)	−0.0047 (9)
C14	0.0305 (13)	0.0264 (13)	0.0266 (11)	0.0005 (11)	0.0043 (9)	0.0008 (9)
C15	0.0302 (13)	0.0247 (13)	0.0336 (11)	−0.0027 (11)	−0.0029 (9)	−0.0019 (10)
C16	0.0536 (17)	0.0411 (17)	0.0318 (12)	−0.0137 (14)	0.0024 (11)	−0.0090 (11)
C17	0.0483 (17)	0.0366 (16)	0.0337 (12)	−0.0024 (13)	0.0133 (11)	0.0013 (11)
C18	0.0280 (12)	0.0224 (13)	0.0207 (10)	0.0004 (10)	0.0026 (8)	−0.0021 (8)
C19	0.0286 (13)	0.0261 (14)	0.0296 (11)	0.0041 (11)	−0.0028 (9)	0.0000 (9)
C20	0.0393 (15)	0.0213 (13)	0.0349 (12)	0.0077 (11)	0.0005 (10)	−0.0017 (10)
C21	0.0364 (14)	0.0240 (13)	0.0283 (11)	−0.0024 (11)	0.0042 (10)	−0.0028 (9)
C22	0.0255 (12)	0.0261 (13)	0.0236 (10)	−0.0030 (10)	0.0021 (8)	−0.0004 (8)
C23	0.0265 (12)	0.0211 (12)	0.0246 (10)	0.0021 (10)	0.0018 (9)	−0.0004 (9)

O1—C1	1.378 (2)	C11—C17	1.531 (3)
O1—C13	1.381 (2)	C11—C16	1.538 (3)
O2—C9	1.230 (3)	C11—C12	1.540 (3)
O3—C5	1.230 (3)	C12—C13	1.492 (3)
O4—N1	1.227 (2)	C12—H12A	0.9900
O5—N1	1.231 (2)	C12—H12B	0.9900
N1—C22	1.472 (3)	C14—H14A	0.9800
C1—C6	1.340 (3)	C14—H14B	0.9800
C1—C2	1.488 (3)	C14—H14C	0.9800
C2—C3	1.533 (3)	C15—H15A	0.9800
C2—H2A	0.9900	C15—H15B	0.9800
C2—H2B	0.9900	C15—H15C	0.9800
C3—C14	1.531 (3)	C16—H16A	0.9800
C3—C4	1.532 (3)	C16—H16B	0.9800
C3—C15	1.533 (3)	C16—H16C	0.9800
C4—C5	1.507 (3)	C17—H17A	0.9800
C4—H4A	0.9900	C17—H17B	0.9800
C4—H4B	0.9900	C17—H17C	0.9800
C5—C6	1.474 (3)	C18—C19	1.389 (3)
C6—C7	1.515 (3)	C18—C23	1.397 (3)
C7—C8	1.510 (3)	C19—C20	1.389 (3)
C7—C18	1.534 (3)	C19—H19	0.9500
C7—H7	1.0000	C20—C21	1.385 (3)
C8—C13	1.338 (3)	C20—H20	0.9500
C8—C9	1.471 (3)	C21—C22	1.388 (3)
C9—C10	1.510 (3)	C21—H21	0.9500
C10—C11	1.528 (3)	C22—C23	1.385 (3)
C10—H10A	0.9900	C23—H23	0.9500
C10—H10B	0.9900
C1—O1—C13	117.83 (17)	C17—C11—C12	108.93 (19)
O4—N1—O5	124.0 (2)	C16—C11—C12	110.6 (2)
O4—N1—C22	117.83 (19)	C13—C12—C11	112.29 (18)
O5—N1—C22	118.1 (2)	C13—C12—H12A	109.1
C6—C1—O1	123.00 (18)	C11—C12—H12A	109.1
C6—C1—C2	125.82 (18)	C13—C12—H12B	109.1
O1—C1—C2	111.17 (17)	C11—C12—H12B	109.1
C1—C2—C3	112.65 (18)	H12A—C12—H12B	107.9
C1—C2—H2A	109.1	C8—C13—O1	122.81 (19)
C3—C2—H2A	109.1	C8—C13—C12	126.15 (19)
C1—C2—H2B	109.1	O1—C13—C12	111.04 (18)
C3—C2—H2B	109.1	C3—C14—H14A	109.5
H2A—C2—H2B	107.8	C3—C14—H14B	109.5
C14—C3—C4	109.77 (17)	H14A—C14—H14B	109.5
C14—C3—C15	108.71 (18)	C3—C14—H14C	109.5
C4—C3—C15	110.81 (18)	H14A—C14—H14C	109.5
C14—C3—C2	110.01 (17)	H14B—C14—H14C	109.5
C4—C3—C2	107.53 (18)	C3—C15—H15A	109.5
C15—C3—C2	109.99 (17)	C3—C15—H15B	109.5
C5—C4—C3	113.96 (17)	H15A—C15—H15B	109.5
C5—C4—H4A	108.8	C3—C15—H15C	109.5
C3—C4—H4A	108.8	H15A—C15—H15C	109.5
C5—C4—H4B	108.8	H15B—C15—H15C	109.5
C3—C4—H4B	108.8	C11—C16—H16A	109.5
H4A—C4—H4B	107.7	C11—C16—H16B	109.5
O3—C5—C6	120.21 (19)	H16A—C16—H16B	109.5
O3—C5—C4	122.31 (19)	C11—C16—H16C	109.5
C6—C5—C4	117.45 (19)	H16A—C16—H16C	109.5
C1—C6—C5	118.54 (19)	H16B—C16—H16C	109.5
C1—C6—C7	123.00 (18)	C11—C17—H17A	109.5
C5—C6—C7	118.46 (18)	C11—C17—H17B	109.5
C8—C7—C6	108.39 (18)	H17A—C17—H17B	109.5
C8—C7—C18	111.21 (16)	C11—C17—H17C	109.5
C6—C7—C18	112.29 (18)	H17A—C17—H17C	109.5
C8—C7—H7	108.3	H17B—C17—H17C	109.5
C6—C7—H7	108.3	C19—C18—C23	118.5 (2)
C18—C7—H7	108.3	C19—C18—C7	121.75 (19)
C13—C8—C9	118.4 (2)	C23—C18—C7	119.76 (19)
C13—C8—C7	123.21 (19)	C18—C19—C20	121.7 (2)
C9—C8—C7	118.37 (19)	C18—C19—H19	119.2
O2—C9—C8	120.0 (2)	C20—C19—H19	119.2
O2—C9—C10	122.4 (2)	C21—C20—C19	120.4 (2)
C8—C9—C10	117.6 (2)	C21—C20—H20	119.8
C9—C10—C11	113.83 (19)	C19—C20—H20	119.8
C9—C10—H10A	108.8	C20—C21—C22	117.3 (2)
C11—C10—H10A	108.8	C20—C21—H21	121.4
C9—C10—H10B	108.8	C22—C21—H21	121.4
C11—C10—H10B	108.8	C23—C22—C21	123.4 (2)
H10A—C10—H10B	107.7	C23—C22—N1	118.3 (2)
C10—C11—C17	109.7 (2)	C21—C22—N1	118.3 (2)
C10—C11—C16	110.3 (2)	C22—C23—C18	118.7 (2)
C17—C11—C16	109.38 (19)	C22—C23—H23	120.7
C10—C11—C12	107.88 (18)	C18—C23—H23	120.7
C13—O1—C1—C6	6.2 (3)	C8—C9—C10—C11	32.6 (3)
C13—O1—C1—C2	−172.70 (17)	C9—C10—C11—C17	−173.52 (19)
C6—C1—C2—C3	22.0 (3)	C9—C10—C11—C16	65.9 (2)
O1—C1—C2—C3	−159.20 (17)	C9—C10—C11—C12	−55.0 (3)
C1—C2—C3—C14	−167.45 (17)	C10—C11—C12—C13	46.8 (2)
C1—C2—C3—C4	−47.9 (2)	C17—C11—C12—C13	165.81 (19)
C1—C2—C3—C15	72.8 (2)	C16—C11—C12—C13	−73.9 (2)
C14—C3—C4—C5	174.59 (18)	C9—C8—C13—O1	172.13 (18)
C15—C3—C4—C5	−65.3 (2)	C7—C8—C13—O1	−7.0 (3)
C2—C3—C4—C5	54.9 (2)	C9—C8—C13—C12	−7.8 (3)
C3—C4—C5—O3	148.0 (2)	C7—C8—C13—C12	173.1 (2)
C3—C4—C5—C6	−34.1 (3)	C1—O1—C13—C8	−4.3 (3)
O1—C1—C6—C5	−176.97 (18)	C1—O1—C13—C12	175.67 (17)
C2—C1—C6—C5	1.8 (3)	C11—C12—C13—C8	−17.4 (3)
O1—C1—C6—C7	3.2 (3)	C11—C12—C13—O1	162.64 (18)
C2—C1—C6—C7	−178.1 (2)	C8—C7—C18—C19	−112.2 (2)
O3—C5—C6—C1	−177.9 (2)	C6—C7—C18—C19	126.2 (2)
C4—C5—C6—C1	4.3 (3)	C8—C7—C18—C23	66.7 (2)
O3—C5—C6—C7	2.0 (3)	C6—C7—C18—C23	−54.9 (2)
C4—C5—C6—C7	−175.89 (18)	C23—C18—C19—C20	2.0 (3)
C1—C6—C7—C8	−12.4 (3)	C7—C18—C19—C20	−179.1 (2)
C5—C6—C7—C8	167.72 (18)	C18—C19—C20—C21	−0.6 (3)
C1—C6—C7—C18	110.8 (2)	C19—C20—C21—C22	−0.6 (3)
C5—C6—C7—C18	−69.0 (2)	C20—C21—C22—C23	0.4 (3)
C6—C7—C8—C13	14.3 (3)	C20—C21—C22—N1	−178.68 (18)
C18—C7—C8—C13	−109.6 (2)	O4—N1—C22—C23	−13.9 (3)
C6—C7—C8—C9	−164.80 (18)	O5—N1—C22—C23	166.23 (19)
C18—C7—C8—C9	71.3 (2)	O4—N1—C22—C21	165.2 (2)
C13—C8—C9—O2	−176.5 (2)	O5—N1—C22—C21	−14.7 (3)
C7—C8—C9—O2	2.6 (3)	C21—C22—C23—C18	1.0 (3)
C13—C8—C9—C10	0.2 (3)	N1—C22—C23—C18	−179.92 (17)
C7—C8—C9—C10	179.30 (19)	C19—C18—C23—C22	−2.2 (3)
O2—C9—C10—C11	−150.8 (2)	C7—C18—C23—C22	178.92 (18)