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

In the title compound, C(23)H(24)N(2)O(7), the central 4H-pyran ring adopts a flattened boat conformation, whereas both cyclo-hexenone rings adopt envelope conformations, the C atom bearing the dimethyl substituent being the flap atom in each case. The mean and maximum deviation of the pyran ring are 0.0379 (4) and 0.0605 (3) Å. The mean plane of the pyran ring and the dinitro-benzene ring make a dihedral angle of 85.88 (2)°.

Related literature

For the synthesis of xanthenes, see: Vanag & Stankevich (1960 ▶); Hilderbrand & Weissleder (2007 ▶). For their pharmaceutical properties, see: Dimmock et al. (1988 ▶); Lambert et al. (1997 ▶); Poupelin et al. (1978 ▶); Hideo (1981 ▶); Selvanayagam et al. (1996 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Odabaşoğlu et al. (2008 ▶); Reddy et al. (2009 ▶); Mehdi et al. (2011 ▶); Sughanya & Sureshbabu (2012 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H24N2O7

M = 440.44

Monoclinic,

a = 9.7733 (3) Å

b = 19.6193 (5) Å

c = 11.7922 (3) Å

β = 109.603 (1)°

V = 2130.04 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.905, T max = 0.975

29785 measured reflections

7327 independent reflections

4793 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.159

S = 1.03

7327 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001384/im2418sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001384/im2418Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001384/im2418Isup3.cml

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

C23H24N2O7	F(000) = 928
Mr = 440.44	Dx = 1.373 Mg m−3
Monoclinic, P21/c	Melting point: 446 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.7733 (3) Å	Cell parameters from 8512 reflections
b = 19.6193 (5) Å	θ = 2.2–31.1°
c = 11.7922 (3) Å	µ = 0.10 mm−1
β = 109.603 (1)°	T = 296 K
V = 2130.04 (10) Å3	Block, yellow
Z = 4	0.35 × 0.30 × 0.25 mm

Bruker Kappa APEXII CCD diffractometer	7327 independent reflections
Radiation source: fine-focus sealed tube	4793 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scan	θmax = 32.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
Tmin = 0.905, Tmax = 0.975	k = −29→27
29785 measured reflections	l = −15→17

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0777P)2 + 0.3517P] where P = (Fo2 + 2Fc2)/3
7327 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.30 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
C1	0.51973 (13)	0.15131 (7)	0.58305 (11)	0.0339 (3)
C2	0.41933 (15)	0.19984 (8)	0.61245 (13)	0.0434 (3)
H2A	0.4760	0.2353	0.6648	0.052*
H2B	0.3659	0.1758	0.6561	0.052*
C3	0.31152 (14)	0.23285 (8)	0.50052 (13)	0.0397 (3)
C4	0.24534 (14)	0.17645 (8)	0.40933 (14)	0.0432 (3)
H4A	0.1827	0.1488	0.4393	0.052*
H4B	0.1851	0.1973	0.3347	0.052*
C5	0.35407 (13)	0.13059 (7)	0.38268 (12)	0.0372 (3)
C6	0.49306 (12)	0.11891 (7)	0.47847 (11)	0.0325 (3)
C7	0.59949 (13)	0.06997 (6)	0.45403 (10)	0.0303 (2)
H7	0.5504	0.0265	0.4260	0.036*
C8	0.72373 (13)	0.05827 (6)	0.56996 (11)	0.0309 (2)
C9	0.83150 (13)	0.00583 (7)	0.57141 (11)	0.0338 (3)
C10	0.95370 (15)	−0.00702 (7)	0.68746 (12)	0.0393 (3)
H10A	1.0378	−0.0227	0.6687	0.047*
H10B	0.9251	−0.0433	0.7308	0.047*
C11	0.99723 (14)	0.05519 (7)	0.76956 (12)	0.0383 (3)
C12	0.85972 (15)	0.08387 (8)	0.78692 (11)	0.0406 (3)
H12A	0.8279	0.0530	0.8374	0.049*
H12B	0.8822	0.1274	0.8281	0.049*
C13	0.73989 (13)	0.09328 (7)	0.67058 (11)	0.0330 (3)
C14	0.38929 (18)	0.28478 (9)	0.44734 (16)	0.0541 (4)
H14A	0.4308	0.3198	0.5056	0.081*
H14B	0.3210	0.3048	0.3766	0.081*
H14C	0.4649	0.2624	0.4264	0.081*
C15	0.19240 (17)	0.26822 (10)	0.53505 (17)	0.0551 (4)
H15A	0.2344	0.3036	0.5925	0.083*
H15B	0.1449	0.2356	0.5699	0.083*
H15C	0.1228	0.2878	0.4645	0.083*
C16	1.10517 (18)	0.03431 (10)	0.89168 (14)	0.0594 (5)
H16A	1.0614	0.0007	0.9279	0.089*
H16B	1.1313	0.0736	0.9431	0.089*
H16C	1.1906	0.0155	0.8808	0.089*
C17	1.06762 (17)	0.10848 (9)	0.71315 (15)	0.0509 (4)
H17A	1.0003	0.1220	0.6365	0.076*
H17B	1.1530	0.0896	0.7023	0.076*
H17C	1.0940	0.1475	0.7651	0.076*
C18	0.65475 (12)	0.09886 (6)	0.35707 (10)	0.0295 (2)
C19	0.61732 (13)	0.07634 (7)	0.23872 (11)	0.0313 (2)
C20	0.66867 (14)	0.10639 (7)	0.15506 (11)	0.0361 (3)
H20	0.6414	0.0904	0.0764	0.043*
C21	0.76167 (14)	0.16090 (7)	0.19241 (12)	0.0379 (3)
C22	0.80053 (16)	0.18654 (8)	0.30670 (13)	0.0425 (3)
H22	0.8618	0.2241	0.3294	0.051*
C23	0.74630 (15)	0.15511 (7)	0.38759 (12)	0.0382 (3)
H23	0.7721	0.1723	0.4655	0.046*
N1	0.51735 (13)	0.01863 (7)	0.19194 (10)	0.0422 (3)
N2	0.81838 (16)	0.19342 (8)	0.10531 (13)	0.0543 (4)
O1	0.64491 (10)	0.14292 (5)	0.67914 (8)	0.0384 (2)
O2	0.32732 (11)	0.10217 (6)	0.28536 (9)	0.0516 (3)
O3	0.81924 (12)	−0.02696 (6)	0.48107 (9)	0.0491 (3)
O4	0.52780 (15)	−0.03162 (6)	0.25373 (11)	0.0642 (4)
O5	0.42986 (15)	0.02476 (8)	0.09097 (11)	0.0723 (4)
O6	0.7810 (2)	0.17153 (9)	0.00386 (14)	0.0984 (6)
O7	0.89653 (17)	0.24275 (8)	0.13837 (14)	0.0805 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0318 (5)	0.0406 (7)	0.0304 (6)	0.0049 (5)	0.0120 (5)	0.0037 (5)
C2	0.0425 (7)	0.0530 (9)	0.0372 (7)	0.0145 (6)	0.0168 (6)	0.0015 (6)
C3	0.0347 (6)	0.0417 (8)	0.0427 (7)	0.0055 (5)	0.0131 (5)	0.0038 (6)
C4	0.0306 (6)	0.0467 (8)	0.0494 (8)	0.0011 (5)	0.0095 (5)	0.0013 (6)
C5	0.0308 (6)	0.0426 (7)	0.0377 (7)	−0.0029 (5)	0.0109 (5)	0.0018 (5)
C6	0.0295 (5)	0.0382 (7)	0.0311 (6)	0.0010 (5)	0.0119 (4)	0.0029 (5)
C7	0.0317 (5)	0.0334 (6)	0.0268 (5)	−0.0018 (5)	0.0109 (4)	−0.0004 (4)
C8	0.0317 (5)	0.0343 (6)	0.0279 (5)	0.0012 (5)	0.0116 (4)	0.0014 (5)
C9	0.0354 (6)	0.0329 (6)	0.0343 (6)	−0.0005 (5)	0.0133 (5)	−0.0013 (5)
C10	0.0377 (6)	0.0379 (7)	0.0400 (7)	0.0065 (5)	0.0099 (5)	−0.0002 (6)
C11	0.0346 (6)	0.0439 (8)	0.0331 (6)	0.0061 (5)	0.0069 (5)	−0.0041 (5)
C12	0.0403 (6)	0.0539 (9)	0.0263 (6)	0.0099 (6)	0.0094 (5)	−0.0011 (5)
C13	0.0328 (5)	0.0394 (7)	0.0283 (6)	0.0063 (5)	0.0125 (4)	0.0025 (5)
C14	0.0495 (8)	0.0476 (9)	0.0650 (10)	−0.0020 (7)	0.0189 (7)	0.0097 (8)
C15	0.0455 (8)	0.0576 (10)	0.0643 (10)	0.0162 (7)	0.0212 (7)	0.0023 (8)
C16	0.0495 (8)	0.0747 (12)	0.0417 (8)	0.0207 (8)	−0.0010 (7)	−0.0062 (8)
C17	0.0452 (8)	0.0524 (9)	0.0559 (9)	−0.0092 (7)	0.0180 (7)	−0.0133 (7)
C18	0.0309 (5)	0.0316 (6)	0.0270 (5)	0.0013 (4)	0.0108 (4)	0.0006 (4)
C19	0.0321 (5)	0.0334 (6)	0.0281 (6)	0.0002 (5)	0.0098 (4)	−0.0014 (5)
C20	0.0403 (6)	0.0426 (7)	0.0272 (6)	0.0066 (5)	0.0137 (5)	0.0023 (5)
C21	0.0406 (6)	0.0399 (7)	0.0399 (7)	0.0055 (5)	0.0222 (5)	0.0101 (5)
C22	0.0452 (7)	0.0382 (7)	0.0463 (8)	−0.0086 (6)	0.0183 (6)	0.0017 (6)
C23	0.0444 (7)	0.0381 (7)	0.0328 (6)	−0.0073 (6)	0.0138 (5)	−0.0034 (5)
N1	0.0436 (6)	0.0483 (7)	0.0337 (6)	−0.0087 (5)	0.0115 (5)	−0.0092 (5)
N2	0.0629 (8)	0.0574 (9)	0.0552 (8)	0.0032 (7)	0.0367 (7)	0.0144 (7)
O1	0.0376 (5)	0.0481 (6)	0.0284 (4)	0.0115 (4)	0.0096 (4)	−0.0031 (4)
O2	0.0387 (5)	0.0704 (8)	0.0398 (6)	0.0021 (5)	0.0052 (4)	−0.0092 (5)
O3	0.0528 (6)	0.0513 (6)	0.0419 (6)	0.0084 (5)	0.0141 (5)	−0.0121 (5)
O4	0.0859 (9)	0.0470 (7)	0.0540 (7)	−0.0244 (6)	0.0157 (6)	−0.0048 (5)
O5	0.0660 (8)	0.0897 (10)	0.0424 (6)	−0.0206 (7)	−0.0067 (6)	−0.0088 (6)
O6	0.1521 (16)	0.1066 (13)	0.0657 (9)	−0.0304 (11)	0.0749 (11)	−0.0055 (9)
O7	0.0924 (10)	0.0799 (10)	0.0826 (10)	−0.0268 (8)	0.0471 (8)	0.0168 (8)

C1—C6	1.3331 (18)	C12—H12B	0.9700
C1—O1	1.3702 (15)	C13—O1	1.3723 (15)
C1—C2	1.4892 (18)	C14—H14A	0.9600
C2—C3	1.5293 (19)	C14—H14B	0.9600
C2—H2A	0.9700	C14—H14C	0.9600
C2—H2B	0.9700	C15—H15A	0.9600
C3—C15	1.523 (2)	C15—H15B	0.9600
C3—C14	1.526 (2)	C15—H15C	0.9600
C3—C4	1.527 (2)	C16—H16A	0.9600
C4—C5	1.504 (2)	C16—H16B	0.9600
C4—H4A	0.9700	C16—H16C	0.9600
C4—H4B	0.9700	C17—H17A	0.9600
C5—O2	1.2226 (17)	C17—H17B	0.9600
C5—C6	1.4643 (17)	C17—H17C	0.9600
C6—C7	1.5127 (17)	C18—C23	1.3899 (18)
C7—C8	1.5107 (16)	C18—C19	1.3908 (16)
C7—C18	1.5279 (17)	C19—C20	1.3801 (18)
C7—H7	0.9800	C19—N1	1.4762 (17)
C8—C13	1.3338 (17)	C20—C21	1.377 (2)
C8—C9	1.4683 (17)	C20—H20	0.9300
C9—O3	1.2155 (15)	C21—C22	1.368 (2)
C9—C10	1.5054 (18)	C21—N2	1.4667 (18)
C10—C11	1.5270 (19)	C22—C23	1.3820 (19)
C10—H10A	0.9700	C22—H22	0.9300
C10—H10B	0.9700	C23—H23	0.9300
C11—C17	1.522 (2)	N1—O4	1.2096 (17)
C11—C16	1.5280 (19)	N1—O5	1.2166 (16)
C11—C12	1.5327 (18)	N2—O6	1.207 (2)
C12—C13	1.4864 (17)	N2—O7	1.213 (2)
C12—H12A	0.9700
C6—C1—O1	123.43 (11)	C11—C12—H12B	109.2
C6—C1—C2	125.49 (11)	H12A—C12—H12B	107.9
O1—C1—C2	111.07 (11)	C8—C13—O1	123.36 (11)
C1—C2—C3	112.76 (11)	C8—C13—C12	125.35 (11)
C1—C2—H2A	109.0	O1—C13—C12	111.29 (11)
C3—C2—H2A	109.0	C3—C14—H14A	109.5
C1—C2—H2B	109.0	C3—C14—H14B	109.5
C3—C2—H2B	109.0	H14A—C14—H14B	109.5
H2A—C2—H2B	107.8	C3—C14—H14C	109.5
C15—C3—C14	109.66 (13)	H14A—C14—H14C	109.5
C15—C3—C4	109.71 (12)	H14B—C14—H14C	109.5
C14—C3—C4	110.24 (13)	C3—C15—H15A	109.5
C15—C3—C2	109.23 (12)	C3—C15—H15B	109.5
C14—C3—C2	110.09 (12)	H15A—C15—H15B	109.5
C4—C3—C2	107.89 (12)	C3—C15—H15C	109.5
C5—C4—C3	114.75 (11)	H15A—C15—H15C	109.5
C5—C4—H4A	108.6	H15B—C15—H15C	109.5
C3—C4—H4A	108.6	C11—C16—H16A	109.5
C5—C4—H4B	108.6	C11—C16—H16B	109.5
C3—C4—H4B	108.6	H16A—C16—H16B	109.5
H4A—C4—H4B	107.6	C11—C16—H16C	109.5
O2—C5—C6	120.23 (12)	H16A—C16—H16C	109.5
O2—C5—C4	121.70 (12)	H16B—C16—H16C	109.5
C6—C5—C4	118.04 (12)	C11—C17—H17A	109.5
C1—C6—C5	118.81 (12)	C11—C17—H17B	109.5
C1—C6—C7	123.05 (11)	H17A—C17—H17B	109.5
C5—C6—C7	118.14 (11)	C11—C17—H17C	109.5
C8—C7—C6	108.62 (10)	H17A—C17—H17C	109.5
C8—C7—C18	110.80 (10)	H17B—C17—H17C	109.5
C6—C7—C18	110.21 (10)	C23—C18—C19	116.22 (11)
C8—C7—H7	109.1	C23—C18—C7	117.34 (11)
C6—C7—H7	109.1	C19—C18—C7	126.38 (11)
C18—C7—H7	109.1	C20—C19—C18	123.04 (12)
C13—C8—C9	118.70 (11)	C20—C19—N1	114.48 (11)
C13—C8—C7	123.10 (11)	C18—C19—N1	122.48 (11)
C9—C8—C7	118.21 (11)	C21—C20—C19	117.55 (12)
O3—C9—C8	120.08 (12)	C21—C20—H20	121.2
O3—C9—C10	121.53 (12)	C19—C20—H20	121.2
C8—C9—C10	118.37 (11)	C22—C21—C20	122.43 (12)
C9—C10—C11	114.19 (11)	C22—C21—N2	119.00 (13)
C9—C10—H10A	108.7	C20—C21—N2	118.56 (13)
C11—C10—H10A	108.7	C21—C22—C23	118.17 (13)
C9—C10—H10B	108.7	C21—C22—H22	120.9
C11—C10—H10B	108.7	C23—C22—H22	120.9
H10A—C10—H10B	107.6	C22—C23—C18	122.56 (12)
C17—C11—C10	110.04 (12)	C22—C23—H23	118.7
C17—C11—C16	109.01 (13)	C18—C23—H23	118.7
C10—C11—C16	109.91 (12)	O4—N1—O5	124.03 (13)
C17—C11—C12	110.57 (12)	O4—N1—C19	119.24 (11)
C10—C11—C12	107.93 (11)	O5—N1—C19	116.72 (13)
C16—C11—C12	109.37 (11)	O6—N2—O7	123.44 (15)
C13—C12—C11	112.15 (11)	O6—N2—C21	118.66 (15)
C13—C12—H12A	109.2	O7—N2—C21	117.84 (15)
C11—C12—H12A	109.2	C1—O1—C13	117.56 (10)
C13—C12—H12B	109.2
C6—C1—C2—C3	−24.1 (2)	C16—C11—C12—C13	−169.45 (14)
O1—C1—C2—C3	156.81 (12)	C9—C8—C13—O1	−179.49 (11)
C1—C2—C3—C15	166.99 (13)	C7—C8—C13—O1	0.5 (2)
C1—C2—C3—C14	−72.55 (17)	C9—C8—C13—C12	−0.1 (2)
C1—C2—C3—C4	47.79 (16)	C7—C8—C13—C12	179.97 (12)
C15—C3—C4—C5	−170.89 (13)	C11—C12—C13—C8	26.1 (2)
C14—C3—C4—C5	68.26 (16)	C11—C12—C13—O1	−154.43 (12)
C2—C3—C4—C5	−51.99 (16)	C8—C7—C18—C23	−50.45 (15)
C3—C4—C5—O2	−151.35 (14)	C6—C7—C18—C23	69.81 (14)
C3—C4—C5—C6	30.51 (18)	C8—C7—C18—C19	132.67 (13)
O1—C1—C6—C5	178.65 (12)	C6—C7—C18—C19	−107.07 (14)
C2—C1—C6—C5	−0.3 (2)	C23—C18—C19—C20	1.15 (19)
O1—C1—C6—C7	−0.9 (2)	C7—C18—C19—C20	178.06 (12)
C2—C1—C6—C7	−179.87 (13)	C23—C18—C19—N1	−178.00 (12)
O2—C5—C6—C1	179.17 (13)	C7—C18—C19—N1	−1.09 (19)
C4—C5—C6—C1	−2.66 (19)	C18—C19—C20—C21	0.32 (19)
O2—C5—C6—C7	−1.26 (19)	N1—C19—C20—C21	179.54 (11)
C4—C5—C6—C7	176.91 (12)	C19—C20—C21—C22	−1.7 (2)
C1—C6—C7—C8	7.67 (17)	C19—C20—C21—N2	179.64 (12)
C5—C6—C7—C8	−171.88 (11)	C20—C21—C22—C23	1.5 (2)
C1—C6—C7—C18	−113.88 (13)	N2—C21—C22—C23	−179.84 (13)
C5—C6—C7—C18	66.57 (14)	C21—C22—C23—C18	0.1 (2)
C6—C7—C8—C13	−7.50 (17)	C19—C18—C23—C22	−1.4 (2)
C18—C7—C8—C13	113.70 (13)	C7—C18—C23—C22	−178.56 (13)
C6—C7—C8—C9	172.53 (11)	C20—C19—N1—O4	138.94 (14)
C18—C7—C8—C9	−66.27 (14)	C18—C19—N1—O4	−41.84 (19)
C13—C8—C9—O3	179.81 (13)	C20—C19—N1—O5	−39.93 (18)
C7—C8—C9—O3	−0.22 (19)	C18—C19—N1—O5	139.28 (14)
C13—C8—C9—C10	1.31 (18)	C22—C21—N2—O6	−178.31 (17)
C7—C8—C9—C10	−178.72 (11)	C20—C21—N2—O6	0.4 (2)
O3—C9—C10—C11	152.40 (13)	C22—C21—N2—O7	−1.0 (2)
C8—C9—C10—C11	−29.12 (17)	C20—C21—N2—O7	177.70 (15)
C9—C10—C11—C17	−68.38 (15)	C6—C1—O1—C13	−7.06 (19)
C9—C10—C11—C16	171.56 (12)	C2—C1—O1—C13	172.05 (12)
C9—C10—C11—C12	52.36 (16)	C8—C13—O1—C1	7.24 (19)
C17—C11—C12—C13	70.50 (16)	C12—C13—O1—C1	−172.26 (11)
C10—C11—C12—C13	−49.90 (16)