3-(2,4-Dimeth­oxy­anilino)-8-meth­oxy­dibenz[b,e]oxepin-11(6H)-one

Baur, B.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536811002637

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o487

doi:10.1107/S1600536811002637

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3-(2,4-Dimethoxyanilino)-8-methoxydibenz[b,e]oxepin-11(6H)-one

Benjamin Baur,^a Dieter Schollmeyer ^b and Stefan Laufer ^a ^*

^aInstitute of Pharmacy, Department of Pharmaceutical Chemistry, Eberhard Karls University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and ^bDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duessbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 18 January 2011; accepted 19 January 2011; online 26 January 2011)

In the title compound, C₂₃H₂₁NO₅, the two benzene rings of the tricyclic unit are oriented at a dihedral angle of 37.5 (8)°. The 2,4-dimethoxyanilino residue is oriented at a dihedral angle of 60.2 (8)° towards the phenoxy ring. In the crystal, the central carbonyl O atom accepts two hydrogen bonds from the N—H and C—H groups. A further intermolecular C—H⋯O interaction involving one of the methoxy O atoms is also observed.

Related literature

For palladium-catalysed amination reactions of aryl halides with anilines, see: Jensen et al. (2004 ). For p38 MAP kinase inhibitors based on dibenzo[b,e]oxepin-11(6H)-one, see: Laufer et al. (2006 ).

Experimental

Crystal data

C₂₃H₂₁NO₅
M_r = 391.41
Monoclinic, P 2₁ /c
a = 9.3277 (9) Å
b = 25.8290 (8) Å
c = 7.9519 (6) Å
β = 98.914 (3)°
V = 1892.7 (2) Å³
Z = 4
Cu Kα radiation
μ = 0.80 mm⁻¹
T = 193 K
0.50 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
3847 measured reflections
3578 independent reflections
3041 reflections with I > 2σ(I)
R_int = 0.021
3 standard reflections every 60 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.111
S = 1.06
3578 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N12—H12⋯O23ⁱ	0.87	2.08	2.9403 (18)	168
C4—H4⋯O23ⁱ	0.95	2.57	3.3000 (19)	134
C20—H20B⋯O21ⁱⁱ	0.98	2.56	3.496 (3)	160
Symmetry codes: (i) x, y, z-1; (ii) -x+2, -y+1, -z-1.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002637/nc2218sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002637/nc2218Isup2.hkl

checkCIF report

Comment top

Based on dibenzo[b,e]oxepin-11(6H)-one (Laufer et al. 2006) as novel p38 MAP kinase inhibitors, our intent was to synthesize new oxepin derivatives. The title compound was synthesized in the course of an ongoing study to insert hydrophilic residues at position 8. The two phenyl rings of the tricyclid unit are oriented at a dihedral angle of 37.5 (8°). The 2,4-dimethoxyphenylamino residue is oriented at a dihedral angel of 60.2 (8°) towards the phenoxy ring. The crystal stucture is characterized by several hydrogen bonds. The central carboxyl group O(23) forms two hydrogen bonds towards N(12)—H (2.08 Å) and C(4)—H (2.57 Å) and O(21) forms a hydrogen bond towards C(20)—H (2.56 Å) (Tab. 1).

Related literature top

For palladium-catalysed amination reactions of aryl halides with anilines, see: Jensen et al. (2004). For p38 MAP kinase inhibitors based on dibenzo[b,e]oxepin-11(6H)-one, see: Laufer et al. (2006).

Experimental top

The preparation of the title compound was achieved by using a palladium catalyzed amination reaction (Jensen et al. (2004)).

A mixture of 200 mg (0.73 mmol) 3-chloro-9-methoxy-dibenzo[b,e]oxepin-11(6H)-one, 120 mg (0.78 mmol) 2–4-dimethoxyaniline, 1.10 g (3.37 mmol) Cs₂CO₃, 45 mg (0.10 mmol) 2-(dicyclohexylphosphino)-2`-4`-6`-triisopropylbiphenyl and 20 mg (0.09 mmol) Pd(OAc)₂ in 2 ml absolute tert-butanol and 10 ml absolute 2.4-dioxane was stirred for 1 h at 284 K under an argon atmosphere. The mixture was then filtered and evaporated under pressure. The residue was purified by column chromatography (SiO_2, n-hexane / ethyl acetate 1 + 1). Crystals of the title compound were obtained by slow evaporation of the solvent from a solution of the title compound in diethylether / n-hexane.

¹H NMR (200 MHz, DMSO) δ in p.p.m. 3.75 (s, 3 H), 3.77 (s, 3 H), 3.84 (s, 3 H), 5.10 (s, 2 H), 6.11 (d, J=2.27 Hz, 1 H), 6.52 (m, 2 H), 6.66 (m, 1 H), 7.07 (m, 3 H), 7.82 (d, J=7.96 Hz, 1 H), 7.95 (d, J=8.97 Hz, 1 H), 8.17 (s, 1 H)

¹³C NMR (50 MHz, DMSO) δ in p.p.m. 55.7, 55.9, 55.9, 73.4, 100.0, 101.0, 105.1, 109.6, 113.2, 114.6, 116.2, 121.7, 126.7, 132.0, 132.9, 133.6, 138.9, 153.8, 154.9, 158.2, 162.6, 163.1, 185.4

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. Crystal structure of the title compound with labelling and displacement ellipsoids are drawn at the 50% probability level.

6-[(2,4-dimethoxyphenyl)amino]-13-methoxy-9-oxatricyclo[9.4.0.0^3,8]pentadeca- 1(11),3(8),4,6,12,14-hexaen-2-one top

Crystal data top

C₂₃H₂₁NO₅	F(000) = 824
M_r = 391.41	D_x = 1.374 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.3277 (9) Å	θ = 61–68°
b = 25.8290 (8) Å	µ = 0.80 mm⁻¹
c = 7.9519 (6) Å	T = 193 K
β = 98.914 (3)°	Needle, yellow
V = 1892.7 (2) Å³	0.50 × 0.10 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.021
Radiation source: rotating anode	θ_max = 69.9°, θ_min = 3.4°
Graphite monochromator	h = −11→11
ω/2θ scans	k = 0→31
3847 measured reflections	l = 0→9
3578 independent reflections	3 standard reflections every 60 min
3041 reflections with I > 2σ(I)	intensity decay: 1%

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0517P)² + 0.6681P] where P = (F_o² + 2F_c²)/3
3578 reflections	(Δ/σ)_max < 0.001
265 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₃H₂₁NO₅	V = 1892.7 (2) Å³
M_r = 391.41	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 9.3277 (9) Å	µ = 0.80 mm⁻¹
b = 25.8290 (8) Å	T = 193 K
c = 7.9519 (6) Å	0.50 × 0.10 × 0.10 mm
β = 98.914 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.021
3847 measured reflections	3 standard reflections every 60 min
3578 independent reflections	intensity decay: 1%
3041 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
3578 reflections	Δρ_min = −0.25 e Å⁻³
265 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.02652 (18)	0.28134 (6)	0.3263 (2)	0.0231 (3)
H1	−0.0153	0.2542	0.2545	0.028*
C1A	0.16914 (17)	0.29698 (6)	0.32152 (19)	0.0203 (3)
C2	0.25880 (19)	0.26887 (6)	0.2104 (2)	0.0239 (4)
H2A	0.3481	0.2556	0.2807	0.029*
H2B	0.2035	0.2389	0.1567	0.029*
O3	0.29732 (12)	0.30244 (5)	0.08016 (13)	0.0249 (3)
C3A	0.41536 (17)	0.33353 (6)	0.1250 (2)	0.0196 (3)
C4	0.48724 (17)	0.34554 (6)	−0.0096 (2)	0.0211 (3)
H4	0.4503	0.3328	−0.1199	0.025*
C5	0.61280 (17)	0.37589 (6)	0.01266 (19)	0.0206 (3)
C6	0.66950 (18)	0.39254 (6)	0.1786 (2)	0.0231 (3)
H6	0.7579	0.4114	0.1991	0.028*
C7	0.59571 (18)	0.38115 (6)	0.3098 (2)	0.0239 (3)
H7	0.6347	0.3931	0.4205	0.029*
C7A	0.46456 (17)	0.35261 (6)	0.29013 (19)	0.0197 (3)
C8	0.38732 (18)	0.35207 (6)	0.43906 (19)	0.0220 (3)
C8A	0.23163 (18)	0.33692 (6)	0.42594 (19)	0.0212 (3)
C9	0.14745 (19)	0.36140 (7)	0.5343 (2)	0.0266 (4)
H9	0.1886	0.3887	0.6061	0.032*
C10	0.00634 (19)	0.34659 (7)	0.5384 (2)	0.0279 (4)
H10	−0.0498	0.3642	0.6104	0.034*
C11	−0.05416 (18)	0.30576 (7)	0.4367 (2)	0.0241 (4)
N12	0.67328 (15)	0.38860 (6)	−0.12843 (17)	0.0258 (3)
H12	0.6152	0.3845	−0.2242	0.031*
C13	0.80880 (17)	0.41301 (6)	−0.12979 (19)	0.0217 (3)
C14	0.81422 (17)	0.45637 (6)	−0.2367 (2)	0.0220 (3)
C15	0.94631 (18)	0.47876 (6)	−0.2511 (2)	0.0240 (4)
H15	0.9501	0.5074	−0.3251	0.029*
C16	1.07366 (17)	0.45964 (6)	−0.1579 (2)	0.0233 (4)
C17	1.07033 (18)	0.41758 (7)	−0.0502 (2)	0.0260 (4)
H17	1.1571	0.4047	0.0145	0.031*
C18	0.93686 (19)	0.39460 (7)	−0.0391 (2)	0.0256 (4)
H18	0.9340	0.3654	0.0330	0.031*
O19	0.68401 (12)	0.47311 (5)	−0.32059 (16)	0.0289 (3)
C20	0.6874 (2)	0.51958 (8)	−0.4183 (3)	0.0404 (5)
H20A	0.5880	0.5303	−0.4631	0.061*
H20B	0.7408	0.5132	−0.5132	0.061*
H20C	0.7357	0.5471	−0.3456	0.061*
O21	1.19612 (13)	0.48548 (5)	−0.18470 (17)	0.0333 (3)
C22	1.33194 (19)	0.46751 (9)	−0.0997 (3)	0.0386 (5)
H22A	1.3330	0.4691	0.0237	0.058*
H22B	1.4097	0.4894	−0.1306	0.058*
H22C	1.3469	0.4317	−0.1333	0.058*
O23	0.44763 (14)	0.36837 (5)	0.57752 (14)	0.0338 (3)
O24	−0.19058 (13)	0.29162 (5)	0.45756 (16)	0.0319 (3)
C25	−0.2614 (2)	0.25277 (8)	0.3469 (3)	0.0399 (5)
H25A	−0.2687	0.2644	0.2285	0.060*
H25B	−0.3589	0.2466	0.3741	0.060*
H25C	−0.2052	0.2206	0.3619	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0268 (8)	0.0244 (8)	0.0184 (8)	−0.0034 (7)	0.0049 (6)	−0.0003 (6)
C1A	0.0267 (8)	0.0212 (8)	0.0136 (7)	−0.0013 (6)	0.0051 (6)	0.0025 (6)
C2	0.0306 (9)	0.0223 (8)	0.0212 (8)	−0.0073 (7)	0.0117 (7)	−0.0024 (6)
O3	0.0293 (6)	0.0327 (6)	0.0140 (5)	−0.0121 (5)	0.0074 (5)	−0.0038 (5)
C3A	0.0211 (8)	0.0202 (7)	0.0183 (7)	−0.0006 (6)	0.0053 (6)	−0.0005 (6)
C4	0.0262 (8)	0.0235 (8)	0.0141 (7)	−0.0010 (6)	0.0049 (6)	−0.0008 (6)
C5	0.0242 (8)	0.0209 (8)	0.0176 (7)	0.0007 (6)	0.0060 (6)	0.0026 (6)
C6	0.0239 (8)	0.0251 (8)	0.0204 (8)	−0.0050 (6)	0.0042 (6)	0.0000 (6)
C7	0.0278 (8)	0.0278 (8)	0.0154 (7)	−0.0023 (7)	0.0015 (6)	−0.0013 (6)
C7A	0.0231 (8)	0.0227 (8)	0.0136 (7)	−0.0014 (6)	0.0039 (6)	0.0012 (6)
C8	0.0297 (9)	0.0223 (8)	0.0140 (7)	−0.0027 (7)	0.0038 (6)	0.0010 (6)
C8A	0.0281 (8)	0.0228 (8)	0.0138 (7)	−0.0014 (7)	0.0067 (6)	0.0017 (6)
C9	0.0370 (9)	0.0234 (8)	0.0211 (8)	−0.0025 (7)	0.0099 (7)	−0.0032 (7)
C10	0.0326 (9)	0.0279 (9)	0.0266 (9)	0.0039 (7)	0.0148 (7)	−0.0013 (7)
C11	0.0245 (8)	0.0281 (9)	0.0209 (8)	0.0026 (7)	0.0072 (7)	0.0053 (6)
N12	0.0259 (7)	0.0372 (8)	0.0147 (7)	−0.0093 (6)	0.0045 (5)	0.0017 (6)
C13	0.0256 (8)	0.0255 (8)	0.0158 (7)	−0.0039 (7)	0.0086 (6)	−0.0028 (6)
C14	0.0234 (8)	0.0259 (8)	0.0175 (7)	0.0004 (6)	0.0055 (6)	−0.0015 (6)
C15	0.0285 (9)	0.0231 (8)	0.0213 (8)	−0.0027 (7)	0.0071 (7)	0.0017 (6)
C16	0.0235 (8)	0.0255 (8)	0.0224 (8)	−0.0029 (7)	0.0079 (7)	−0.0048 (6)
C17	0.0254 (8)	0.0292 (9)	0.0229 (8)	0.0020 (7)	0.0021 (7)	−0.0003 (7)
C18	0.0317 (9)	0.0267 (9)	0.0192 (8)	−0.0012 (7)	0.0071 (7)	0.0036 (7)
O19	0.0242 (6)	0.0307 (7)	0.0312 (7)	−0.0013 (5)	0.0026 (5)	0.0085 (5)
C20	0.0358 (10)	0.0361 (11)	0.0467 (12)	0.0000 (8)	−0.0015 (9)	0.0184 (9)
O21	0.0220 (6)	0.0365 (7)	0.0416 (7)	−0.0069 (5)	0.0053 (5)	0.0051 (6)
C22	0.0219 (9)	0.0518 (12)	0.0410 (11)	−0.0060 (8)	0.0010 (8)	0.0010 (9)
O23	0.0369 (7)	0.0508 (8)	0.0140 (6)	−0.0133 (6)	0.0041 (5)	−0.0057 (5)
O24	0.0264 (6)	0.0390 (7)	0.0327 (7)	−0.0023 (5)	0.0120 (5)	0.0003 (6)
C25	0.0294 (10)	0.0460 (12)	0.0459 (12)	−0.0084 (9)	0.0108 (9)	−0.0038 (10)

Geometric parameters (Å, º) top

C1—C11	1.393 (2)	C11—O24	1.358 (2)
C1—C1A	1.396 (2)	N12—C13	1.414 (2)
C1—H1	0.9500	N12—H12	0.8699
C1A—C8A	1.394 (2)	C13—C18	1.381 (2)
C1A—C2	1.496 (2)	C13—C14	1.412 (2)
C2—O3	1.4382 (19)	C14—O19	1.362 (2)
C2—H2A	0.9900	C14—C15	1.382 (2)
C2—H2B	0.9900	C15—C16	1.390 (2)
O3—C3A	1.3648 (19)	C15—H15	0.9500
C3A—C4	1.383 (2)	C16—O21	1.3680 (19)
C3A—C7A	1.411 (2)	C16—C17	1.386 (2)
C4—C5	1.398 (2)	C17—C18	1.394 (2)
C4—H4	0.9500	C17—H17	0.9500
C5—N12	1.371 (2)	C18—H18	0.9500
C5—C6	1.411 (2)	O19—C20	1.433 (2)
C6—C7	1.368 (2)	C20—H20A	0.9800
C6—H6	0.9500	C20—H20B	0.9800
C7—C7A	1.416 (2)	C20—H20C	0.9800
C7—H7	0.9500	O21—C22	1.418 (2)
C7A—C8	1.479 (2)	C22—H22A	0.9800
C8—O23	1.2304 (19)	C22—H22B	0.9800
C8—C8A	1.492 (2)	C22—H22C	0.9800
C8A—C9	1.403 (2)	O24—C25	1.428 (2)
C9—C10	1.376 (2)	C25—H25A	0.9800
C9—H9	0.9500	C25—H25B	0.9800
C10—C11	1.394 (2)	C25—H25C	0.9800
C10—H10	0.9500

C11—C1—C1A	119.75 (15)	O24—C11—C10	115.82 (15)
C11—C1—H1	120.1	C1—C11—C10	119.89 (15)
C1A—C1—H1	120.1	C5—N12—C13	126.48 (14)
C8A—C1A—C1	120.67 (15)	C5—N12—H12	114.1
C8A—C1A—C2	119.38 (14)	C13—N12—H12	118.9
C1—C1A—C2	119.87 (14)	C18—C13—C14	118.62 (15)
O3—C2—C1A	110.96 (13)	C18—C13—N12	122.99 (15)
O3—C2—H2A	109.4	C14—C13—N12	118.28 (14)
C1A—C2—H2A	109.4	O19—C14—C15	124.42 (15)
O3—C2—H2B	109.4	O19—C14—C13	115.74 (14)
C1A—C2—H2B	109.4	C15—C14—C13	119.83 (15)
H2A—C2—H2B	108.0	C14—C15—C16	120.43 (15)
C3A—O3—C2	116.61 (12)	C14—C15—H15	119.8
O3—C3A—C4	113.44 (14)	C16—C15—H15	119.8
O3—C3A—C7A	125.57 (14)	O21—C16—C17	125.29 (15)
C4—C3A—C7A	120.99 (14)	O21—C16—C15	114.13 (15)
C3A—C4—C5	121.68 (15)	C17—C16—C15	120.58 (15)
C3A—C4—H4	119.2	C16—C17—C18	118.58 (16)
C5—C4—H4	119.2	C16—C17—H17	120.7
N12—C5—C4	118.28 (14)	C18—C17—H17	120.7
N12—C5—C6	123.38 (14)	C13—C18—C17	121.93 (15)
C4—C5—C6	118.33 (14)	C13—C18—H18	119.0
C7—C6—C5	119.20 (15)	C17—C18—H18	119.0
C7—C6—H6	120.4	C14—O19—C20	116.01 (13)
C5—C6—H6	120.4	O19—C20—H20A	109.5
C6—C7—C7A	123.77 (15)	O19—C20—H20B	109.5
C6—C7—H7	118.1	H20A—C20—H20B	109.5
C7A—C7—H7	118.1	O19—C20—H20C	109.5
C3A—C7A—C7	115.82 (14)	H20A—C20—H20C	109.5
C3A—C7A—C8	127.84 (14)	H20B—C20—H20C	109.5
C7—C7A—C8	115.86 (14)	C16—O21—C22	118.15 (14)
O23—C8—C7A	120.10 (15)	O21—C22—H22A	109.5
O23—C8—C8A	117.22 (14)	O21—C22—H22B	109.5
C7A—C8—C8A	122.43 (13)	H22A—C22—H22B	109.5
C1A—C8A—C9	118.50 (15)	O21—C22—H22C	109.5
C1A—C8A—C8	123.26 (14)	H22A—C22—H22C	109.5
C9—C8A—C8	118.04 (14)	H22B—C22—H22C	109.5
C10—C9—C8A	121.18 (16)	C11—O24—C25	117.80 (14)
C10—C9—H9	119.4	O24—C25—H25A	109.5
C8A—C9—H9	119.4	O24—C25—H25B	109.5
C9—C10—C11	119.97 (15)	H25A—C25—H25B	109.5
C9—C10—H10	120.0	O24—C25—H25C	109.5
C11—C10—H10	120.0	H25A—C25—H25C	109.5
O24—C11—C1	124.26 (16)	H25B—C25—H25C	109.5

C11—C1—C1A—C8A	−0.2 (2)	C7A—C8—C8A—C9	−146.90 (16)
C11—C1—C1A—C2	176.53 (15)	C1A—C8A—C9—C10	0.0 (2)
C8A—C1A—C2—O3	−66.78 (19)	C8—C8A—C9—C10	−174.98 (15)
C1—C1A—C2—O3	116.48 (16)	C8A—C9—C10—C11	1.6 (3)
C1A—C2—O3—C3A	83.27 (17)	C1A—C1—C11—O24	−176.31 (15)
C2—O3—C3A—C4	151.24 (14)	C1A—C1—C11—C10	1.8 (2)
C2—O3—C3A—C7A	−28.6 (2)	C9—C10—C11—O24	175.75 (15)
O3—C3A—C4—C5	−178.36 (14)	C9—C10—C11—C1	−2.5 (3)
C7A—C3A—C4—C5	1.5 (2)	C4—C5—N12—C13	−171.32 (15)
C3A—C4—C5—N12	−176.34 (15)	C6—C5—N12—C13	9.7 (3)
C3A—C4—C5—C6	2.7 (2)	C5—N12—C13—C18	53.5 (2)
N12—C5—C6—C7	175.15 (16)	C5—N12—C13—C14	−130.35 (17)
C4—C5—C6—C7	−3.8 (2)	C18—C13—C14—O19	−179.03 (14)
C5—C6—C7—C7A	0.9 (3)	N12—C13—C14—O19	4.6 (2)
O3—C3A—C7A—C7	175.56 (15)	C18—C13—C14—C15	1.2 (2)
C4—C3A—C7A—C7	−4.3 (2)	N12—C13—C14—C15	−175.09 (14)
O3—C3A—C7A—C8	−12.8 (3)	O19—C14—C15—C16	178.75 (15)
C4—C3A—C7A—C8	167.39 (16)	C13—C14—C15—C16	−1.5 (2)
C6—C7—C7A—C3A	3.1 (2)	C14—C15—C16—O21	179.95 (15)
C6—C7—C7A—C8	−169.56 (16)	C14—C15—C16—C17	0.6 (2)
C3A—C7A—C8—O23	176.92 (16)	O21—C16—C17—C18	−178.63 (16)
C7—C7A—C8—O23	−11.4 (2)	C15—C16—C17—C18	0.7 (2)
C3A—C7A—C8—C8A	−9.0 (3)	C14—C13—C18—C17	0.0 (2)
C7—C7A—C8—C8A	162.71 (15)	N12—C13—C18—C17	176.18 (15)
C1—C1A—C8A—C9	−0.7 (2)	C16—C17—C18—C13	−1.0 (3)
C2—C1A—C8A—C9	−177.46 (15)	C15—C14—O19—C20	−5.2 (2)
C1—C1A—C8A—C8	173.99 (15)	C13—C14—O19—C20	175.09 (16)
C2—C1A—C8A—C8	−2.7 (2)	C17—C16—O21—C22	1.6 (3)
O23—C8—C8A—C1A	−147.38 (16)	C15—C16—O21—C22	−177.76 (16)
C7A—C8—C8A—C1A	38.3 (2)	C1—C11—O24—C25	−6.7 (2)
O23—C8—C8A—C9	27.4 (2)	C10—C11—O24—C25	175.15 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O23ⁱ	0.87	2.08	2.9403 (18)	168
C4—H4···O23ⁱ	0.95	2.57	3.3000 (19)	134
C20—H20B···O21ⁱⁱ	0.98	2.56	3.496 (3)	160

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₁NO₅
M_r	391.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	9.3277 (9), 25.8290 (8), 7.9519 (6)
β (°)	98.914 (3)
V (Å³)	1892.7 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.50 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3847, 3578, 3041
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.111, 1.06
No. of reflections	3578
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.25

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CORINC (Dräger & Gattow, 1971), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O23ⁱ	0.87	2.08	2.9403 (18)	168
C4—H4···O23ⁱ	0.95	2.57	3.3000 (19)	134
C20—H20B···O21ⁱⁱ	0.98	2.56	3.496 (3)	160

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

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761–762. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Jensen, T. A., Liang, X., Tanner, D. & Skjaerbaek, N. (2004). J. Org. Chem. 69, 4936–4947 Web of Science CrossRef PubMed CAS Google Scholar
Laufer, S. A., Ahrens, G. M., Karcher, S. C., Hering, J. S. & Niess, R. (2006). J. Med. Chem. 49, 7912–7915. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page o487

doi:10.1107/S1600536811002637

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