9,9-Dimethyl-12-(4-nitro­phen­yl)-9,10-dihydro-12H-benzo[a]xanthen-11(8H)-one

Li, D.-L.; Wang, L.-H.

doi:10.1107/S1600536809048570

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3141

doi:10.1107/S1600536809048570

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9,9-Dimethyl-12-(4-nitrophenyl)-9,10-dihydro-12H-benzo[a]xanthen-11(8H)-one

De-Ling Li ^a ^* and Li-Hong Wang ^a

^aDepartment of Chemistry, Tangshan Normal College, Tangshan 063000, People's Republic of China
^*Correspondence e-mail: deling1@126.com

(Received 30 October 2009; accepted 16 November 2009; online 21 November 2009)

In the molecular structure of the title compound, C₂₅H₂₁NO₄, the pyran ring adopts a flattened boat conformation, while the cyclohexenone ring is in an envelope conformation. The 4-nitrophenyl ring is almost perpendicular to the pyran ring [dihedral angle = 89.39 (1)°]. In the crystal, molecules are connected by intermolecular 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_r = 399.43
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.055
wR(F²) = 0.153
S = 1.03
4007 reflections
274 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) $[-x, y-1, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Xanthenes and benzoxanthenes are biologically important drug intermediates. They are cited as active oxygen heterocycles possessing anti-inflammatory (Poupelin et al., 1978) and antiviral (Lambert et al., 1997) activity. These compounds are also utilized as antagonists for paralyzing action of zoxazolamine (Saint-Ruf et al., 1975) and in photodynamic therapy (Ion et al., 1998). We report herein the crystal structure of the title compound, which belongs to this class of compounds.

The pyran ring of the title molecule (Fig. 1) adopts a flattened boat conformation. The cyclohexenone ring is in an envelope conformation with atom C15 at the flap. The 4-nitrophenyl ring and the planar part of the pyran ring (C1/C10/C12/C17) are nearly perpendicular to each other, with a dihedral angle of 89.39 (1)°. In the crystal, the molecules are connected by C—H···O hydrogen bonds (Fig. 2).

Related literature top

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 top

To a mixture of 2-naphthol (1.0 mmol), benzaldehyde (1.0 mmol), and 5,5-dimethylcyclohexane-1,3-dione (1.1 mmol) was added strontium trifluoromethanesulfonate (0.1 mmol) in 1,2-dichloroethane (2 ml). The mixture was stirred at 353 K for 5 h. The progress of the reaction was monitored by TLC. After completion of the reaction, water was added and the product was extracted with ethyl acetate (3×10 ml). The organic layer was dried (MgSO₄) and evaporated, and the crude product was purified by flash chromatography on silica gel. Pure product crystallized slowly at room temperature in ethanol. A single-crystal was obtained by slow evaporation of a solution in ethanol.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The packing, showing hydrogen-bond interactions as dashed lines; H atoms are shown as small spheres of arbitrary radii.

9,9-Dimethyl-12-(4-nitrophenyl)-9,10-dihydro-12H- benzo[a]xanthen-11(8H)-one top

Crystal data top

C₂₅H₂₁NO₄	F(000) = 1680
M_r = 399.43	D_x = 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

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4007 independent reflections
Radiation source: rotating anode	3106 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.044
Detector resolution: 7.31 pixels mm^-1	θ_max = 26.0°, θ_min = 2.1°
ω and ϕ scans	h = −29→26
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→12
T_min = 0.983, T_max = 0.999	l = −18→21
14653 measured reflections

Refinement top

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(F_o²) + (0.0882P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4007 reflections	Δρ_max = 0.29 e Å⁻³
274 parameters	Δρ_min = −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

Crystal data top

C₂₅H₂₁NO₄	V = 4063.9 (19) Å³
M_r = 399.43	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.178 (5) Å	µ = 0.09 mm⁻¹
b = 11.078 (2) Å	T = 113 K
c = 17.481 (4) Å	0.20 × 0.18 × 0.10 mm
β = 119.78 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4007 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3106 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.999	R_int = 0.044
14653 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
4007 reflections	Δρ_min = −0.26 e Å⁻³
274 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y−1, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₁NO₄
M_r	399.43
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	113
a, b, c (Å)	24.178 (5), 11.078 (2), 17.481 (4)
β (°)	119.78 (3)
V (Å³)	4063.9 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.983, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections	14653, 4007, 3106
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.153, 1.03
No. of reflections	4007
No. of parameters	274
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.26

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4ⁱ	0.95	2.42	3.323 (3)	158.5
C6—H6···O2ⁱⁱ	0.95	2.45	3.384 (3)	168.3
C18—H18B···O2ⁱⁱⁱ	0.98	2.43	3.355 (2)	158.0

Symmetry codes: (i) −x, y−1, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

The authors thank the Tangshan Municipal Science and Technology Commission (No. 07160213B) and Tangshan Normal College (No. 07 A02) for financial support.

References

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