3,19-Diacetyl-12-nitro­methyl-14-deoxy­andrographolide

Jia, J.; Yao, C.

doi:10.1107/S160053680904402X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2965

https://doi.org/10.1107/S160053680904402X

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3,19-Diacetyl-12-nitromethyl-14-deoxyandrographolide

Juan Jia ^a and Cheng Yao ^a ^*

^aCollege of Science, Nanjing University of Technolgy, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: yaocheng@njut.edu.cn

(Received 15 October 2009; accepted 23 October 2009; online 31 October 2009)

In the crystal of the title compound, C₂₄H₃₃NO₉, intermolecular C—H⋯O hydrogen bonds link the molecules.

Related literature

For general background, see: Thunuguntla et al. (2004 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₄H₃₃NO₉
M_r = 479.51
Monoclinic, P 2₁
a = 10.533 (2) Å
b = 12.756 (3) Å
c = 10.659 (2) Å
β = 117.04 (3)°
V = 1275.6 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2565 measured reflections
2431 independent reflections
1945 reflections with I > 2σ(I)
R_int = 0.024
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.199
S = 1.00
2431 reflections
302 parameters
14 restraints
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O8ⁱ	0.97	2.59	3.312 (18)	131
C22—H22A⋯O9ⁱⁱ	0.97	2.47	3.388 (13)	158
C22—H22B⋯O1ⁱⁱⁱ	0.97	2.51	3.301 (13)	139
C24—H24B⋯O3^iv	0.97	2.56	3.376 (9)	142
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (iv) x+1, y, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680904402X/hb5144sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680904402X/hb5144Isup2.hkl

checkCIF report

Related literature top

For general background, see: Thunuguntla et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

Andrographolide (15 g) and nitromethane (20 ml) in dry methanol were stired in the presence of sodium methoxide at room temperature for 3 h. After confirming the completion of reaction, the mixture was washed with brine. The organic phase was evaporated in vacuo, and the residue was recrystallized by ethyl acrtate. The product (10 g) and acetic anhydride (20 ml) was refluxed for 10 min. After confirming the completion of reaction, the mixture was washed with brine. The organic phase was evaporated in vacuo to afford corresponding product by flash chromatography. Colourless blocks of (I) were recrystallised from ethyl acetate.

Structure description top

For general background, see: Thunuguntla et al. (2004). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids.

3,19-Diacetyl-12-nitromethyl-14-deoxyandrographolide top

Crystal data top

C₂₄H₃₃NO₉	F(000) = 512
M_r = 479.51	D_x = 1.248 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 10.533 (2) Å	θ = 9–12°
b = 12.756 (3) Å	µ = 0.10 mm⁻¹
c = 10.659 (2) Å	T = 293 K
β = 117.04 (3)°	Block, colourless
V = 1275.6 (4) Å³	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.024
Radiation source: fine-focus sealed tube	θ_max = 25.3°, θ_min = 2.2°
Graphite monochromator	h = −11→12
ω/2θ scans	k = −15→0
2565 measured reflections	l = −12→0
2431 independent reflections	3 standard reflections every 200 reflections
1945 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.072	H-atom parameters constrained
wR(F²) = 0.199	w = 1/[σ²(F_o²) + (0.1P)² + 1.120P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2431 reflections	Δρ_max = 0.69 e Å⁻³
302 parameters	Δρ_min = −0.48 e Å⁻³
14 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.063 (8)

Crystal data top

C₂₄H₃₃NO₉	V = 1275.6 (4) Å³
M_r = 479.51	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.533 (2) Å	µ = 0.10 mm⁻¹
b = 12.756 (3) Å	T = 293 K
c = 10.659 (2) Å	0.30 × 0.20 × 0.20 mm
β = 117.04 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.024
2565 measured reflections	3 standard reflections every 200 reflections
2431 independent reflections	intensity decay: 1%
1945 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.072	14 restraints
wR(F²) = 0.199	H-atom parameters constrained
S = 1.00	Δρ_max = 0.69 e Å⁻³
2431 reflections	Δρ_min = −0.48 e Å⁻³
302 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N	0.7992 (9)	−0.3512 (6)	0.7140 (12)	0.1177 (19)
O1	0.1814 (7)	0.3398 (4)	0.6418 (6)	0.0915 (17)
C1	0.0804 (12)	0.4065 (7)	0.7867 (12)	0.108 (3)
H1A	0.0769	0.4728	0.7427	0.162*
H1B	0.1387	0.4127	0.8866	0.162*
H1C	−0.0143	0.3859	0.7679	0.162*
O2	0.1466 (6)	0.2330 (3)	0.7887 (5)	0.0719 (13)
C2	0.1425 (7)	0.3259 (5)	0.7293 (8)	0.0645 (16)
O3	−0.1429 (6)	−0.0145 (5)	0.8828 (7)	0.0935 (18)
C3	−0.1806 (8)	0.1612 (7)	0.9391 (9)	0.084 (2)
H3A	−0.2668	0.1342	0.9365	0.126*
H3B	−0.2033	0.2160	0.8704	0.126*
H3C	−0.1207	0.1887	1.0312	0.126*
O4	0.0165 (4)	0.1100 (3)	0.9106 (4)	0.0555 (10)
C4	−0.1040 (7)	0.0749 (5)	0.9066 (6)	0.0587 (15)
C5	0.1112 (7)	0.0355 (5)	0.8929 (6)	0.0559 (14)
H5A	0.0813	−0.0350	0.9011	0.067*
H5B	0.2070	0.0454	0.9681	0.067*
C6	0.1141 (6)	0.0463 (5)	0.7499 (5)	0.0470 (12)
O5	0.3609 (8)	−0.3524 (5)	0.7817 (8)	0.115 (2)
C7	0.1806 (6)	−0.0527 (4)	0.7167 (5)	0.0424 (12)
H7A	0.1659	−0.0412	0.6201	0.051*
O6	0.4623 (8)	−0.1819 (6)	0.3207 (5)	0.106 (2)
C8	0.3456 (6)	−0.0689 (4)	0.8036 (5)	0.0456 (12)
O7	0.4337 (11)	−0.3352 (6)	0.4088 (7)	0.145 (3)
O8	0.8651 (14)	−0.3399 (8)	0.6600 (15)	0.218 (7)
C9	0.4175 (7)	0.0340 (5)	0.7949 (8)	0.0644 (16)
H9A	0.5187	0.0294	0.8580	0.077*
H9B	0.4063	0.0420	0.6999	0.077*
O9	0.7740 (7)	−0.4391 (5)	0.7441 (9)	0.1177 (19)
C10	0.3570 (7)	0.1318 (5)	0.8330 (8)	0.0655 (17)
H10A	0.3776	0.1280	0.9313	0.079*
H10B	0.4038	0.1937	0.8209	0.079*
C11	0.2003 (7)	0.1420 (4)	0.7444 (7)	0.0558 (14)
H11A	0.1817	0.1527	0.6465	0.067*
C12	−0.0425 (6)	0.0581 (5)	0.6332 (6)	0.0596 (15)
H12A	−0.0433	0.0659	0.5433	0.089*
H12B	−0.0848	0.1188	0.6523	0.089*
H12C	−0.0959	−0.0032	0.6321	0.089*
C13	0.3944 (7)	−0.0991 (5)	0.9598 (6)	0.0595 (15)
H13A	0.3676	−0.0447	1.0053	0.089*
H13B	0.4961	−0.1075	1.0066	0.089*
H13C	0.3498	−0.1637	0.9640	0.089*
C14	0.0996 (6)	−0.1543 (4)	0.7078 (6)	0.0522 (13)
H14A	−0.0017	−0.1426	0.6505	0.063*
H14B	0.1150	−0.1743	0.8014	0.063*
C15	0.1489 (7)	−0.2431 (5)	0.6436 (7)	0.0616 (16)
H15A	0.1009	−0.3075	0.6453	0.074*
H15B	0.1234	−0.2267	0.5462	0.074*
C16	0.3051 (6)	−0.2581 (5)	0.7227 (6)	0.0524 (13)
C17	0.3904 (6)	−0.1603 (4)	0.7310 (6)	0.0467 (12)
H17A	0.3592	−0.1379	0.6334	0.056*
C18	0.5504 (6)	−0.1759 (5)	0.7935 (6)	0.0554 (13)
H18A	0.5837	−0.2095	0.8847	0.066*
H18B	0.5959	−0.1078	0.8086	0.066*
C19	0.5979 (6)	−0.2425 (5)	0.7016 (6)	0.0526 (14)
H19A	0.5479	−0.3098	0.6836	0.063*
C20	0.5592 (6)	−0.1911 (5)	0.5610 (6)	0.0524 (13)
C21	0.4825 (11)	−0.2478 (8)	0.4296 (8)	0.087 (2)
C22	0.5278 (9)	−0.0844 (7)	0.3765 (9)	0.088 (2)
H22A	0.4587	−0.0279	0.3415	0.105*
H22B	0.6036	−0.0701	0.3511	0.105*
C23	0.5853 (8)	−0.0952 (6)	0.5302 (8)	0.0693 (17)
H23A	0.6326	−0.0428	0.5957	0.083*
C24	0.7548 (7)	−0.2639 (5)	0.7812 (8)	0.0649 (16)
H24A	0.7784	−0.2830	0.8774	0.078*
H24B	0.8072	−0.2008	0.7838	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.109 (3)	0.059 (2)	0.196 (6)	0.008 (3)	0.079 (4)	−0.003 (3)
O1	0.128 (5)	0.059 (3)	0.100 (4)	0.001 (3)	0.062 (4)	0.019 (3)
C1	0.147 (8)	0.051 (4)	0.152 (9)	0.012 (5)	0.090 (7)	0.001 (5)
O2	0.112 (4)	0.036 (2)	0.090 (3)	0.001 (2)	0.066 (3)	0.002 (2)
C2	0.068 (4)	0.037 (3)	0.083 (4)	0.001 (3)	0.030 (3)	0.007 (3)
O3	0.114 (4)	0.073 (3)	0.120 (4)	−0.029 (3)	0.077 (4)	−0.020 (3)
C3	0.072 (4)	0.097 (6)	0.093 (5)	0.009 (4)	0.046 (4)	−0.015 (5)
O4	0.066 (2)	0.047 (2)	0.062 (2)	−0.0022 (19)	0.037 (2)	−0.0078 (18)
C4	0.069 (4)	0.061 (4)	0.054 (3)	−0.009 (3)	0.035 (3)	−0.007 (3)
C5	0.072 (4)	0.055 (3)	0.051 (3)	0.006 (3)	0.036 (3)	−0.001 (3)
C6	0.061 (3)	0.043 (3)	0.040 (3)	−0.001 (3)	0.026 (2)	0.000 (2)
O5	0.157 (6)	0.081 (4)	0.128 (5)	0.010 (4)	0.082 (5)	0.007 (4)
C7	0.049 (3)	0.044 (3)	0.036 (2)	−0.002 (2)	0.021 (2)	−0.001 (2)
O6	0.155 (6)	0.095 (4)	0.065 (3)	−0.007 (4)	0.048 (3)	0.000 (3)
C8	0.051 (3)	0.043 (3)	0.044 (3)	−0.002 (2)	0.022 (2)	−0.005 (2)
O7	0.241 (9)	0.085 (5)	0.084 (4)	−0.049 (6)	0.054 (5)	−0.028 (4)
O8	0.294 (13)	0.122 (7)	0.410 (18)	−0.038 (8)	0.310 (15)	−0.057 (9)
C9	0.062 (3)	0.044 (3)	0.092 (5)	−0.008 (3)	0.039 (3)	−0.005 (3)
O9	0.109 (3)	0.059 (2)	0.196 (6)	0.008 (3)	0.079 (4)	−0.003 (3)
C10	0.075 (4)	0.038 (3)	0.088 (5)	−0.010 (3)	0.040 (4)	−0.011 (3)
C11	0.078 (4)	0.036 (3)	0.062 (3)	0.002 (3)	0.040 (3)	0.000 (3)
C12	0.065 (3)	0.058 (4)	0.053 (3)	0.008 (3)	0.023 (3)	0.002 (3)
C13	0.072 (4)	0.060 (4)	0.044 (3)	0.009 (3)	0.023 (3)	−0.006 (3)
C14	0.053 (3)	0.048 (3)	0.061 (3)	−0.003 (3)	0.030 (3)	−0.007 (3)
C15	0.059 (4)	0.054 (4)	0.073 (4)	−0.010 (3)	0.031 (3)	−0.019 (3)
C16	0.065 (4)	0.044 (3)	0.056 (3)	0.001 (3)	0.034 (3)	−0.007 (2)
C17	0.051 (3)	0.045 (3)	0.046 (3)	0.003 (2)	0.024 (2)	−0.001 (2)
C18	0.056 (3)	0.054 (3)	0.054 (3)	0.003 (3)	0.023 (3)	−0.003 (3)
C19	0.053 (3)	0.045 (3)	0.062 (3)	0.004 (3)	0.029 (3)	0.001 (3)
C20	0.055 (3)	0.044 (3)	0.066 (3)	0.007 (3)	0.034 (3)	0.001 (3)
C21	0.114 (6)	0.082 (6)	0.069 (5)	−0.005 (5)	0.044 (4)	−0.006 (4)
C22	0.104 (6)	0.083 (6)	0.099 (5)	0.020 (5)	0.066 (5)	0.033 (5)
C23	0.076 (4)	0.059 (4)	0.085 (5)	0.003 (3)	0.048 (4)	0.000 (3)
C24	0.058 (4)	0.047 (3)	0.085 (4)	0.006 (3)	0.029 (3)	0.005 (3)

Geometric parameters (Å, º) top

N—O8	1.094 (10)	C9—H9B	0.9700
N—O9	1.228 (10)	C10—C11	1.488 (9)
N—C24	1.508 (10)	C10—H10A	0.9700
O1—C2	1.190 (8)	C10—H10B	0.9700
C1—C2	1.492 (11)	C11—H11A	0.9800
C1—H1A	0.9600	C12—H12A	0.9600
C1—H1B	0.9600	C12—H12B	0.9600
C1—H1C	0.9600	C12—H12C	0.9600
O2—C2	1.335 (7)	C13—H13A	0.9600
O2—C11	1.460 (7)	C13—H13B	0.9600
O3—C4	1.200 (8)	C13—H13C	0.9600
C3—C4	1.495 (10)	C14—C15	1.531 (8)
C3—H3A	0.9600	C14—H14A	0.9700
C3—H3B	0.9600	C14—H14B	0.9700
C3—H3C	0.9600	C15—C16	1.481 (9)
O4—C4	1.327 (7)	C15—H15A	0.9700
O4—C5	1.451 (7)	C15—H15B	0.9700
C5—C6	1.544 (7)	C16—C17	1.517 (8)
C5—H5A	0.9700	C17—C18	1.518 (7)
C5—H5B	0.9700	C17—H17A	0.9800
C6—C11	1.538 (8)	C18—C19	1.541 (8)
C6—C12	1.557 (8)	C18—H18A	0.9700
C6—C7	1.561 (8)	C18—H18B	0.9700
O5—C16	1.361 (9)	C19—C24	1.500 (8)
C7—C14	1.530 (8)	C19—C20	1.512 (8)
C7—C8	1.568 (7)	C19—H19A	0.9800
C7—H7A	0.9800	C20—C23	1.328 (9)
O6—C21	1.369 (10)	C20—C21	1.452 (10)
O6—C22	1.416 (12)	C22—C23	1.473 (11)
C8—C9	1.539 (8)	C22—H22A	0.9700
C8—C13	1.551 (8)	C22—H22B	0.9700
C8—C17	1.585 (7)	C23—H23A	0.9300
O7—C21	1.205 (12)	C24—H24A	0.9700
C9—C10	1.538 (9)	C24—H24B	0.9700
C9—H9A	0.9700

O8—N—O9	121.4 (10)	C6—C12—H12A	109.5
O8—N—C24	124.1 (9)	C6—C12—H12B	109.5
O9—N—C24	113.5 (9)	H12A—C12—H12B	109.5
C2—C1—H1A	109.5	C6—C12—H12C	109.5
C2—C1—H1B	109.5	H12A—C12—H12C	109.5
H1A—C1—H1B	109.5	H12B—C12—H12C	109.5
C2—C1—H1C	109.5	C8—C13—H13A	109.5
H1A—C1—H1C	109.5	C8—C13—H13B	109.5
H1B—C1—H1C	109.5	H13A—C13—H13B	109.5
C2—O2—C11	119.1 (5)	C8—C13—H13C	109.5
O1—C2—O2	123.8 (7)	H13A—C13—H13C	109.5
O1—C2—C1	126.2 (7)	H13B—C13—H13C	109.5
O2—C2—C1	110.1 (6)	C7—C14—C15	111.2 (5)
C4—C3—H3A	109.5	C7—C14—H14A	109.4
C4—C3—H3B	109.5	C15—C14—H14A	109.4
H3A—C3—H3B	109.5	C7—C14—H14B	109.4
C4—C3—H3C	109.5	C15—C14—H14B	109.4
H3A—C3—H3C	109.5	H14A—C14—H14B	108.0
H3B—C3—H3C	109.5	C16—C15—C14	110.9 (5)
C4—O4—C5	118.6 (5)	C16—C15—H15A	109.5
O3—C4—O4	123.9 (6)	C14—C15—H15A	109.5
O3—C4—C3	125.5 (7)	C16—C15—H15B	109.5
O4—C4—C3	110.7 (6)	C14—C15—H15B	109.5
O4—C5—C6	113.2 (5)	H15A—C15—H15B	108.1
O4—C5—H5A	108.9	O5—C16—C15	120.8 (6)
C6—C5—H5A	108.9	O5—C16—C17	125.5 (6)
O4—C5—H5B	108.9	C15—C16—C17	113.7 (5)
C6—C5—H5B	108.9	C16—C17—C18	115.3 (5)
H5A—C5—H5B	107.8	C16—C17—C8	109.5 (4)
C11—C6—C5	112.6 (5)	C18—C17—C8	113.6 (4)
C11—C6—C12	108.8 (5)	C16—C17—H17A	105.9
C5—C6—C12	108.0 (4)	C18—C17—H17A	105.9
C11—C6—C7	107.5 (4)	C8—C17—H17A	105.9
C5—C6—C7	111.3 (4)	C17—C18—C19	114.2 (5)
C12—C6—C7	108.6 (4)	C17—C18—H18A	108.7
C14—C7—C6	113.9 (4)	C19—C18—H18A	108.7
C14—C7—C8	111.2 (4)	C17—C18—H18B	108.7
C6—C7—C8	117.7 (4)	C19—C18—H18B	108.7
C14—C7—H7A	104.1	H18A—C18—H18B	107.6
C6—C7—H7A	104.1	C24—C19—C20	111.7 (5)
C8—C7—H7A	104.1	C24—C19—C18	109.5 (5)
C21—O6—C22	109.0 (6)	C20—C19—C18	111.9 (5)
C9—C8—C13	110.1 (5)	C24—C19—H19A	107.9
C9—C8—C7	107.2 (4)	C20—C19—H19A	107.9
C13—C8—C7	113.8 (4)	C18—C19—H19A	107.9
C9—C8—C17	109.5 (4)	C23—C20—C21	107.9 (6)
C13—C8—C17	108.3 (4)	C23—C20—C19	130.6 (6)
C7—C8—C17	107.7 (4)	C21—C20—C19	121.5 (6)
C10—C9—C8	113.7 (5)	O7—C21—O6	121.6 (8)
C10—C9—H9A	108.8	O7—C21—C20	129.9 (8)
C8—C9—H9A	108.8	O6—C21—C20	108.4 (7)
C10—C9—H9B	108.8	O6—C22—C23	105.1 (6)
C8—C9—H9B	108.8	O6—C22—H22A	110.7
H9A—C9—H9B	107.7	C23—C22—H22A	110.7
C11—C10—C9	112.1 (5)	O6—C22—H22B	110.7
C11—C10—H10A	109.2	C23—C22—H22B	110.7
C9—C10—H10A	109.2	H22A—C22—H22B	108.8
C11—C10—H10B	109.2	C20—C23—C22	109.5 (7)
C9—C10—H10B	109.2	C20—C23—H23A	125.2
H10A—C10—H10B	107.9	C22—C23—H23A	125.2
O2—C11—C10	110.2 (5)	C19—C24—N	111.5 (6)
O2—C11—C6	107.2 (4)	C19—C24—H24A	109.3
C10—C11—C6	114.2 (5)	N—C24—H24A	109.3
O2—C11—H11A	108.4	C19—C24—H24B	109.3
C10—C11—H11A	108.4	N—C24—H24B	109.3
C6—C11—H11A	108.4	H24A—C24—H24B	108.0

C11—O2—C2—O1	−0.7 (10)	C7—C14—C15—C16	55.1 (7)
C11—O2—C2—C1	178.3 (7)	C14—C15—C16—O5	122.3 (7)
C5—O4—C4—O3	−3.5 (9)	C14—C15—C16—C17	−57.0 (7)
C5—O4—C4—C3	175.1 (5)	O5—C16—C17—C18	8.8 (8)
C4—O4—C5—C6	108.6 (6)	C15—C16—C17—C18	−172.0 (5)
O4—C5—C6—C11	75.4 (6)	O5—C16—C17—C8	−120.8 (6)
O4—C5—C6—C12	−44.7 (7)	C15—C16—C17—C8	58.5 (6)
O4—C5—C6—C7	−163.8 (4)	C9—C8—C17—C16	−172.8 (5)
C11—C6—C7—C14	−175.9 (5)	C13—C8—C17—C16	67.1 (6)
C5—C6—C7—C14	60.3 (6)	C7—C8—C17—C16	−56.5 (5)
C12—C6—C7—C14	−58.4 (6)	C9—C8—C17—C18	56.7 (6)
C11—C6—C7—C8	51.4 (5)	C13—C8—C17—C18	−63.4 (6)
C5—C6—C7—C8	−72.4 (6)	C7—C8—C17—C18	173.0 (4)
C12—C6—C7—C8	168.9 (4)	C16—C17—C18—C19	67.9 (6)
C14—C7—C8—C9	174.9 (5)	C8—C17—C18—C19	−164.6 (5)
C6—C7—C8—C9	−51.2 (6)	C17—C18—C19—C24	−173.0 (5)
C14—C7—C8—C13	−63.1 (6)	C17—C18—C19—C20	62.6 (7)
C6—C7—C8—C13	70.8 (6)	C24—C19—C20—C23	−70.8 (8)
C14—C7—C8—C17	57.1 (5)	C18—C19—C20—C23	52.4 (8)
C6—C7—C8—C17	−169.0 (4)	C24—C19—C20—C21	108.2 (7)
C13—C8—C9—C10	−73.4 (7)	C18—C19—C20—C21	−128.6 (7)
C7—C8—C9—C10	50.9 (7)	C22—O6—C21—O7	178.3 (11)
C17—C8—C9—C10	167.6 (5)	C22—O6—C21—C20	2.0 (9)
C8—C9—C10—C11	−56.1 (8)	C23—C20—C21—O7	−176.9 (12)
C2—O2—C11—C10	89.9 (7)	C19—C20—C21—O7	3.9 (16)
C2—O2—C11—C6	−145.2 (5)	C23—C20—C21—O6	−0.9 (9)
C9—C10—C11—O2	177.3 (5)	C19—C20—C21—O6	179.9 (6)
C9—C10—C11—C6	56.5 (7)	C21—O6—C22—C23	−2.2 (9)
C5—C6—C11—O2	−51.7 (6)	C21—C20—C23—C22	−0.5 (8)
C12—C6—C11—O2	68.0 (6)	C19—C20—C23—C22	178.6 (6)
C7—C6—C11—O2	−174.6 (5)	O6—C22—C23—C20	1.7 (8)
C5—C6—C11—C10	70.7 (6)	C20—C19—C24—N	−70.7 (7)
C12—C6—C11—C10	−169.6 (5)	C18—C19—C24—N	164.7 (6)
C7—C6—C11—C10	−52.3 (6)	O8—N—C24—C19	110.7 (14)
C6—C7—C14—C15	167.4 (5)	O9—N—C24—C19	−80.2 (10)
C8—C7—C14—C15	−56.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O8ⁱ	0.97	2.59	3.312 (18)	131
C22—H22A···O9ⁱⁱ	0.97	2.47	3.388 (13)	158
C22—H22B···O1ⁱⁱⁱ	0.97	2.51	3.301 (13)	139
C24—H24B···O3^iv	0.97	2.56	3.376 (9)	142

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

Experimental details

Crystal data
Chemical formula	C₂₄H₃₃NO₉
M_r	479.51
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	10.533 (2), 12.756 (3), 10.659 (2)
β (°)	117.04 (3)
V (Å³)	1275.6 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2565, 2431, 1945
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.199, 1.00
No. of reflections	2431
No. of parameters	302
No. of restraints	14
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.48

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), 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
C15—H15A···O8ⁱ	0.97	2.59	3.312 (18)	131
C22—H22A···O9ⁱⁱ	0.97	2.47	3.388 (13)	158
C22—H22B···O1ⁱⁱⁱ	0.97	2.51	3.301 (13)	139
C24—H24B···O3^iv	0.97	2.56	3.376 (9)	142

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft. The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thunuguntla, S. S. R., Nyavanandi, V. K. & Nanduri, S. (2004). Tetrahedron Lett. 45, 9357–9360. CAS Google Scholar

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Volume 65| Part 11| November 2009| Page o2965

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