9,9-Dimethyl-12-(4-nitro-phen-yl)-9,10-dihydro-12H-benzo[a]xanthen-11(8H)-one.

In the mol-ecular structure of the title compound, C(25)H(21)NO(4), the pyran ring adopts a flattened boat conformation, while the cyclo-hexenone ring is in an envelope conformation. The 4-nitro-phenyl ring is almost perpendicular to the pyran ring [dihedral angle = 89.39 (1)°]. In the crystal, mol-ecules are connected by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the biological activity of xanthenes and benzoxanthenes, see: Lambert et al. (1997 ▶); Poupelin et al. (1978 ▶); Ion et al. (1998 ▶); Saint-Ruf et al. (1975 ▶).

Experimental

Crystal data

C25H21NO4

M = 399.43

Monoclinic,

a = 24.178 (5) Å

b = 11.078 (2) Å

c = 17.481 (4) Å

β = 119.78 (3)°

V = 4063.9 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.983, T max = 0.999

14653 measured reflections

4007 independent reflections

3106 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.153

S = 1.03

4007 reflections

274 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048570/bh2257sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048570/bh2257Isup2.hkl

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

C25H21NO4	F(000) = 1680
Mr = 399.43	Dx = 1.306 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4847 reflections
a = 24.178 (5) Å	θ = 2.1–27.9°
b = 11.078 (2) Å	µ = 0.09 mm−1
c = 17.481 (4) Å	T = 113 K
β = 119.78 (3)°	Prism, yellow
V = 4063.9 (19) Å3	0.20 × 0.18 × 0.10 mm
Z = 8

Rigaku Saturn CCD area-detector diffractometer	4007 independent reflections
Radiation source: rotating anode	3106 reflections with I > 2σ(I)
confocal	Rint = 0.044
Detector resolution: 7.31 pixels mm-1	θmax = 26.0°, θmin = 2.1°
ω and φ scans	h = −29→26
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→12
Tmin = 0.983, Tmax = 0.999	l = −18→21
14653 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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.153	w = 1/[σ2(Fo2) + (0.0882P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4007 reflections	Δρmax = 0.29 e Å−3
274 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0043 (6)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.07668 (6)	−0.09846 (11)	0.23338 (8)	0.0274 (3)
O2	0.23273 (6)	0.17081 (12)	0.24963 (8)	0.0360 (4)
O3	0.06051 (8)	0.52066 (14)	0.42025 (11)	0.0504 (5)
O4	0.08357 (10)	0.64016 (14)	0.34280 (11)	0.0625 (5)
N1	0.07521 (9)	0.53889 (15)	0.36366 (11)	0.0385 (5)
C1	0.02775 (9)	−0.03873 (17)	0.16146 (11)	0.0247 (4)
C2	−0.03123 (9)	−0.09880 (17)	0.12366 (12)	0.0295 (5)
H2	−0.0351	−0.1738	0.1469	0.035*
C3	−0.08261 (9)	−0.04833 (18)	0.05346 (12)	0.0321 (5)
H3	−0.1227	−0.0880	0.0283	0.038*
C4	−0.07735 (9)	0.06226 (18)	0.01731 (12)	0.0292 (5)
C5	−0.13056 (10)	0.1170 (2)	−0.05572 (13)	0.0365 (5)
H5	−0.1710	0.0787	−0.0805	0.044*
C6	−0.12508 (10)	0.2230 (2)	−0.09105 (13)	0.0397 (6)
H6	−0.1615	0.2591	−0.1388	0.048*
C7	−0.06498 (10)	0.2782 (2)	−0.05608 (12)	0.0370 (5)
H7	−0.0607	0.3505	−0.0819	0.044*
C8	−0.01239 (9)	0.22896 (17)	0.01486 (11)	0.0295 (5)
H8	0.0277	0.2683	0.0378	0.035*
C9	−0.01689 (8)	0.12084 (17)	0.05423 (11)	0.0243 (4)
C10	0.03670 (8)	0.06891 (16)	0.13055 (11)	0.0230 (4)
C11	0.10058 (8)	0.13313 (16)	0.17849 (11)	0.0233 (4)
H11	0.1119	0.1628	0.1340	0.028*
C12	0.15111 (8)	0.04569 (16)	0.23939 (11)	0.0237 (4)
C13	0.21800 (9)	0.07594 (17)	0.27101 (11)	0.0263 (4)
C14	0.26749 (9)	−0.01679 (17)	0.32757 (12)	0.0291 (5)
H14A	0.3089	0.0244	0.3635	0.035*
H14B	0.2727	−0.0752	0.2887	0.035*
C15	0.25060 (9)	−0.08591 (16)	0.38902 (11)	0.0278 (4)
C16	0.18478 (9)	−0.14376 (17)	0.33158 (12)	0.0276 (4)
H16A	0.1893	−0.2140	0.3001	0.033*
H16B	0.1686	−0.1736	0.3701	0.033*
C17	0.13742 (9)	−0.05788 (16)	0.26568 (11)	0.0241 (4)
C18	0.30005 (10)	−0.18485 (18)	0.43696 (13)	0.0361 (5)
H18A	0.3425	−0.1484	0.4702	0.054*
H18B	0.2995	−0.2421	0.3938	0.054*
H18C	0.2899	−0.2275	0.4776	0.054*
C19	0.24992 (10)	0.00103 (19)	0.45700 (12)	0.0350 (5)
H19A	0.2913	0.0418	0.4892	0.052*
H19B	0.2418	−0.0445	0.4985	0.052*
H19C	0.2163	0.0613	0.4266	0.052*
C20	0.09628 (8)	0.24126 (16)	0.22956 (11)	0.0232 (4)
C21	0.10351 (9)	0.35856 (17)	0.20785 (12)	0.0285 (4)
H21	0.1129	0.3716	0.1617	0.034*
C22	0.09739 (10)	0.45691 (18)	0.25190 (12)	0.0323 (5)
H22	0.1023	0.5369	0.2366	0.039*
C23	0.08393 (9)	0.43547 (16)	0.31859 (12)	0.0276 (4)
C24	0.07792 (9)	0.32046 (17)	0.34403 (12)	0.0293 (5)
H24	0.0698	0.3081	0.3914	0.035*
C25	0.08398 (9)	0.22379 (17)	0.29877 (11)	0.0270 (4)
H25	0.0797	0.1440	0.3151	0.032*

	U11	U22	U33	U12	U13	U23
O1	0.0245 (7)	0.0279 (7)	0.0284 (7)	−0.0022 (5)	0.0120 (6)	0.0018 (5)
O2	0.0243 (7)	0.0399 (9)	0.0376 (8)	−0.0038 (6)	0.0108 (6)	0.0098 (6)
O3	0.0587 (11)	0.0439 (10)	0.0597 (10)	−0.0063 (8)	0.0378 (9)	−0.0174 (8)
O4	0.1033 (16)	0.0236 (9)	0.0641 (11)	0.0058 (9)	0.0444 (11)	−0.0003 (8)
N1	0.0419 (11)	0.0297 (10)	0.0373 (10)	0.0006 (8)	0.0146 (8)	−0.0073 (8)
C1	0.0236 (10)	0.0268 (10)	0.0230 (9)	0.0009 (7)	0.0110 (7)	−0.0040 (7)
C2	0.0292 (11)	0.0291 (10)	0.0342 (10)	−0.0044 (8)	0.0189 (8)	−0.0061 (8)
C3	0.0240 (11)	0.0381 (12)	0.0352 (11)	−0.0068 (8)	0.0155 (8)	−0.0149 (9)
C4	0.0229 (10)	0.0370 (11)	0.0268 (10)	0.0015 (8)	0.0116 (8)	−0.0099 (8)
C5	0.0223 (10)	0.0499 (14)	0.0295 (10)	0.0035 (9)	0.0070 (8)	−0.0131 (9)
C6	0.0316 (12)	0.0508 (14)	0.0271 (10)	0.0158 (10)	0.0073 (8)	−0.0033 (10)
C7	0.0407 (13)	0.0418 (13)	0.0253 (10)	0.0114 (10)	0.0140 (9)	0.0018 (9)
C8	0.0288 (11)	0.0347 (11)	0.0238 (9)	0.0054 (8)	0.0123 (8)	−0.0012 (8)
C9	0.0198 (10)	0.0301 (10)	0.0230 (9)	0.0025 (8)	0.0106 (7)	−0.0062 (7)
C10	0.0214 (10)	0.0268 (10)	0.0224 (9)	0.0006 (7)	0.0120 (7)	−0.0037 (7)
C11	0.0208 (9)	0.0258 (10)	0.0237 (9)	0.0000 (7)	0.0113 (7)	0.0006 (7)
C12	0.0216 (10)	0.0270 (10)	0.0213 (9)	0.0005 (7)	0.0097 (7)	−0.0005 (7)
C13	0.0243 (10)	0.0308 (11)	0.0232 (9)	−0.0001 (8)	0.0113 (8)	−0.0012 (8)
C14	0.0213 (10)	0.0326 (11)	0.0305 (10)	0.0031 (8)	0.0107 (8)	0.0007 (8)
C15	0.0262 (11)	0.0280 (10)	0.0263 (10)	0.0051 (8)	0.0108 (8)	0.0006 (8)
C16	0.0293 (11)	0.0257 (10)	0.0270 (9)	0.0017 (8)	0.0134 (8)	0.0018 (8)
C17	0.0210 (10)	0.0269 (10)	0.0238 (9)	−0.0024 (7)	0.0106 (7)	−0.0046 (7)
C18	0.0330 (12)	0.0374 (12)	0.0334 (10)	0.0082 (9)	0.0130 (8)	0.0046 (9)
C19	0.0327 (11)	0.0378 (12)	0.0289 (10)	0.0044 (9)	0.0112 (8)	−0.0031 (9)
C20	0.0174 (9)	0.0247 (10)	0.0235 (9)	−0.0005 (7)	0.0069 (7)	0.0009 (7)
C21	0.0286 (10)	0.0297 (10)	0.0271 (9)	−0.0025 (8)	0.0137 (8)	0.0025 (8)
C22	0.0361 (12)	0.0223 (10)	0.0314 (10)	−0.0022 (8)	0.0115 (9)	0.0028 (8)
C23	0.0263 (10)	0.0225 (10)	0.0276 (10)	0.0003 (8)	0.0084 (8)	−0.0042 (8)
C24	0.0317 (11)	0.0301 (11)	0.0279 (10)	−0.0041 (8)	0.0162 (8)	−0.0051 (8)
C25	0.0301 (10)	0.0232 (10)	0.0276 (10)	−0.0033 (8)	0.0143 (8)	0.0010 (8)

O1—C17	1.362 (2)	C12—C13	1.465 (3)
O1—C1	1.393 (2)	C13—C14	1.513 (3)
O2—C13	1.226 (2)	C14—C15	1.531 (3)
O3—N1	1.223 (2)	C14—H14A	0.9900
O4—N1	1.227 (2)	C14—H14B	0.9900
N1—C23	1.464 (2)	C15—C18	1.529 (2)
C1—C10	1.370 (2)	C15—C19	1.536 (3)
C1—C2	1.406 (3)	C15—C16	1.538 (3)
C2—C3	1.359 (3)	C16—C17	1.494 (3)
C2—H2	0.9500	C16—H16A	0.9900
C3—C4	1.413 (3)	C16—H16B	0.9900
C3—H3	0.9500	C18—H18A	0.9800
C4—C5	1.422 (3)	C18—H18B	0.9800
C4—C9	1.427 (3)	C18—H18C	0.9800
C5—C6	1.364 (3)	C19—H19A	0.9800
C5—H5	0.9500	C19—H19B	0.9800
C6—C7	1.406 (3)	C19—H19C	0.9800
C6—H6	0.9500	C20—C21	1.389 (2)
C7—C8	1.373 (3)	C20—C25	1.395 (3)
C7—H7	0.9500	C21—C22	1.384 (3)
C8—C9	1.412 (3)	C21—H21	0.9500
C8—H8	0.9500	C22—C23	1.378 (3)
C9—C10	1.440 (2)	C22—H22	0.9500
C10—C11	1.519 (2)	C23—C24	1.381 (3)
C11—C12	1.507 (2)	C24—C25	1.382 (2)
C11—C20	1.528 (2)	C24—H24	0.9500
C11—H11	1.0000	C25—H25	0.9500
C12—C17	1.337 (2)
C17—O1—C1	118.36 (14)	C13—C14—H14B	108.9
O3—N1—O4	123.25 (17)	C15—C14—H14B	108.9
O3—N1—C23	118.92 (17)	H14A—C14—H14B	107.7
O4—N1—C23	117.82 (18)	C18—C15—C14	109.56 (16)
C10—C1—O1	122.67 (16)	C18—C15—C19	109.35 (15)
C10—C1—C2	123.27 (17)	C14—C15—C19	109.78 (15)
O1—C1—C2	114.06 (16)	C18—C15—C16	109.46 (15)
C3—C2—C1	119.24 (19)	C14—C15—C16	107.49 (15)
C3—C2—H2	120.4	C19—C15—C16	111.18 (16)
C1—C2—H2	120.4	C17—C16—C15	112.73 (15)
C2—C3—C4	121.03 (18)	C17—C16—H16A	109.0
C2—C3—H3	119.5	C15—C16—H16A	109.0
C4—C3—H3	119.5	C17—C16—H16B	109.0
C3—C4—C5	121.93 (19)	C15—C16—H16B	109.0
C3—C4—C9	119.44 (17)	H16A—C16—H16B	107.8
C5—C4—C9	118.62 (19)	C12—C17—O1	122.74 (16)
C6—C5—C4	121.7 (2)	C12—C17—C16	125.83 (17)
C6—C5—H5	119.1	O1—C17—C16	111.42 (16)
C4—C5—H5	119.1	C15—C18—H18A	109.5
C5—C6—C7	119.32 (19)	C15—C18—H18B	109.5
C5—C6—H6	120.3	H18A—C18—H18B	109.5
C7—C6—H6	120.3	C15—C18—H18C	109.5
C8—C7—C6	120.9 (2)	H18A—C18—H18C	109.5
C8—C7—H7	119.6	H18B—C18—H18C	109.5
C6—C7—H7	119.6	C15—C19—H19A	109.5
C7—C8—C9	121.07 (19)	C15—C19—H19B	109.5
C7—C8—H8	119.5	H19A—C19—H19B	109.5
C9—C8—H8	119.5	C15—C19—H19C	109.5
C8—C9—C4	118.34 (17)	H19A—C19—H19C	109.5
C8—C9—C10	122.60 (17)	H19B—C19—H19C	109.5
C4—C9—C10	119.05 (18)	C21—C20—C25	118.47 (16)
C1—C10—C9	117.88 (17)	C21—C20—C11	121.29 (16)
C1—C10—C11	120.43 (16)	C25—C20—C11	120.23 (16)
C9—C10—C11	121.63 (16)	C22—C21—C20	121.44 (17)
C12—C11—C10	109.51 (15)	C22—C21—H21	119.3
C12—C11—C20	110.94 (14)	C20—C21—H21	119.3
C10—C11—C20	110.11 (14)	C23—C22—C21	118.07 (17)
C12—C11—H11	108.7	C23—C22—H22	121.0
C10—C11—H11	108.7	C21—C22—H22	121.0
C20—C11—H11	108.7	C22—C23—C24	122.59 (17)
C17—C12—C13	118.81 (16)	C22—C23—N1	118.57 (17)
C17—C12—C11	122.81 (17)	C24—C23—N1	118.85 (17)
C13—C12—C11	118.38 (16)	C23—C24—C25	118.20 (17)
O2—C13—C12	120.95 (17)	C23—C24—H24	120.9
O2—C13—C14	121.74 (17)	C25—C24—H24	120.9
C12—C13—C14	117.25 (16)	C24—C25—C20	121.19 (17)
C13—C14—C15	113.47 (16)	C24—C25—H25	119.4
C13—C14—H14A	108.9	C20—C25—H25	119.4
C15—C14—H14A	108.9
C17—O1—C1—C10	−10.1 (2)	C17—C12—C13—C14	3.6 (2)
C17—O1—C1—C2	169.76 (15)	C11—C12—C13—C14	−176.40 (15)
C10—C1—C2—C3	−0.7 (3)	O2—C13—C14—C15	146.74 (17)
O1—C1—C2—C3	179.44 (15)	C12—C13—C14—C15	−35.8 (2)
C1—C2—C3—C4	1.0 (3)	C13—C14—C15—C18	174.83 (15)
C2—C3—C4—C5	−179.58 (17)	C13—C14—C15—C19	−65.1 (2)
C2—C3—C4—C9	1.0 (3)	C13—C14—C15—C16	56.0 (2)
C3—C4—C5—C6	−179.19 (18)	C18—C15—C16—C17	−165.35 (15)
C9—C4—C5—C6	0.2 (3)	C14—C15—C16—C17	−46.4 (2)
C4—C5—C6—C7	1.8 (3)	C19—C15—C16—C17	73.74 (19)
C5—C6—C7—C8	−2.2 (3)	C13—C12—C17—O1	−173.81 (15)
C6—C7—C8—C9	0.7 (3)	C11—C12—C17—O1	6.2 (3)
C7—C8—C9—C4	1.3 (3)	C13—C12—C17—C16	5.4 (3)
C7—C8—C9—C10	−177.74 (17)	C11—C12—C17—C16	−174.52 (16)
C3—C4—C9—C8	177.69 (16)	C1—O1—C17—C12	9.3 (2)
C5—C4—C9—C8	−1.7 (3)	C1—O1—C17—C16	−170.01 (14)
C3—C4—C9—C10	−3.3 (3)	C15—C16—C17—C12	17.8 (3)
C5—C4—C9—C10	177.33 (16)	C15—C16—C17—O1	−162.89 (14)
O1—C1—C10—C9	178.31 (14)	C12—C11—C20—C21	123.51 (18)
C2—C1—C10—C9	−1.6 (3)	C10—C11—C20—C21	−115.09 (19)
O1—C1—C10—C11	−4.4 (3)	C12—C11—C20—C25	−57.4 (2)
C2—C1—C10—C11	175.71 (16)	C10—C11—C20—C25	64.0 (2)
C8—C9—C10—C1	−177.50 (16)	C25—C20—C21—C22	−1.4 (3)
C4—C9—C10—C1	3.5 (3)	C11—C20—C21—C22	177.65 (17)
C8—C9—C10—C11	5.3 (3)	C20—C21—C22—C23	0.1 (3)
C4—C9—C10—C11	−173.76 (15)	C21—C22—C23—C24	1.5 (3)
C1—C10—C11—C12	17.4 (2)	C21—C22—C23—N1	−177.96 (17)
C9—C10—C11—C12	−165.45 (15)	O3—N1—C23—C22	176.83 (18)
C1—C10—C11—C20	−104.88 (19)	O4—N1—C23—C22	−3.7 (3)
C9—C10—C11—C20	72.3 (2)	O3—N1—C23—C24	−2.7 (3)
C10—C11—C12—C17	−18.7 (2)	O4—N1—C23—C24	176.80 (19)
C20—C11—C12—C17	103.10 (19)	C22—C23—C24—C25	−1.8 (3)
C10—C11—C12—C13	161.39 (15)	N1—C23—C24—C25	177.68 (17)
C20—C11—C12—C13	−76.85 (19)	C23—C24—C25—C20	0.4 (3)
C17—C12—C13—O2	−178.88 (17)	C21—C20—C25—C24	1.1 (3)
C11—C12—C13—O2	1.1 (3)	C11—C20—C25—C24	−177.95 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4i	0.95	2.42	3.323 (3)	159
C6—H6···O2ii	0.95	2.45	3.384 (3)	168
C18—H18B···O2iii	0.98	2.43	3.355 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4i	0.95	2.42	3.323 (3)	159
C6—H6⋯O2ii	0.95	2.45	3.384 (3)	168
C18—H18B⋯O2iii	0.98	2.43	3.355 (2)	158

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