tert-Butyl 3-[N-(tert-butoxy­carbonyl)methyl­amino]-4-methoxy­imino-3-methyl­piperidine-1-carboxyl­ate

Wan, Z.; Chai, Y.; Liu, M.; Guo, H.

doi:10.1107/S1600536808044255

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o256

doi:10.1107/S1600536808044255

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tert-Butyl 3-[N-(tert-butoxycarbonyl)methylamino]-4-methoxyimino-3-methylpiperidine-1-carboxylate

Zhilong Wan,^a Yun Chai,^a Mingliang Liu ^a ^* and Huiyuan Guo ^a

^aInstitute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China
^*Correspondence e-mail: lmllyx@yahoo.com.cn

(Received 25 December 2008; accepted 31 December 2008; online 8 January 2009)

The title compound, C₁₈H₃₃N₃O₅, was prepared from N-tert-butoxycarbonyl-4-piperidone using a nine-step reaction, including condensation, methylation, oximation, hydrolysis, esterification, ammonolysis, Hoffmann degradation, tert-butoxycarbonyl protection and methylation. The E configuration of the methyloxime geometry of the compound is confirmed.

Related literature

For the synthesis and properties of quinolone derivatives, see: Anderson & Osheroff (2001 ); Ball et al. (1998 ); Hong et al. (1997 ); Ray et al. (2005 ); Wang et al. (2008 ).

Experimental

Crystal data

C₁₈H₃₃N₃O₅
M_r = 371.47
Monoclinic, C 2/c
a = 28.867 (3) Å
b = 6.1887 (13) Å
c = 25.379 (3) Å
β = 112.769 (2)°
V = 4180.6 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.40 × 0.20 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.963, T_max = 0.991
10032 measured reflections
3699 independent reflections
1915 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.144
S = 1.02
3699 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536808044255/rk2125sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808044255/rk2125Isup2.hkl

checkCIF report

Comment top

Quinolones, a class of synthetic antibacterial compounds based on a 4–quinolone skeleton, have been the landmark discovery in the treatment of bacterial infections in both community and hospital setting (Ray et al., 2005; Ball et al., 1998;). The most intensive structural variations have been carried out on the basic group at the C–7 position, partially due to the ease of their introduction through a nucleophilic aromatic substitution reaction on the corresponding halide. Piperazine, piperidine, pyrrolidine and their derivatives have been the most successfully employed side chains, as evidenced by the compounds currently on the market (Anderson & Osheroff, 2001; Hong et al., 1997). Recently, as part of an ongoing program to find potent new quinolones displaying strong Gram–positive activity, we have focused our attention on introducing new functional groups to the piperidine ring (Wang et al., 2008). We report here the crystal structure of the title compound, which is a key intermediate of 4–methoxyimino–3–methylamino–3–methylpiperidine, a novel C–7 substituent of the quinolones.

The oxime geometry of the title compound was confirmed to have the E–configuration. In the molecule of the compound (Fig. 1), the N1—C6 (1.352 (3) Å) and N2—C12 (1.359 (3) Å) bond lengths are significantly shorter than the normal C—N bond (1.47 Å), indicating some conjugation with the C6═O2 and C12═O4 carbonyl groups, respectively. The six–membered piperidine ring adopts a chair conformation with displacing N1 and C3 atoms (0.593 (3) Å and -0.654 (3) Å respectively) from the mean–plane (C1, C2, C4 and C5).

Related literature top

For the synthesis and properties of quinolone derivatives, see: Anderson & Osheroff (2001); Ball et al. (1998); Hong et al. (1997); Ray et al., (2005); Wang et al. (2008).

Experimental top

To a stirring solution of 1-N-tert-Butoxycarbonyl-3-(N-tert-butoxycarbonyl) amino-4-methoxyimino-3-methylpiperidine(2.4 g, 6.7 mmol) in dry tetrahydrofuran (40 ml) was added 70% sodium hydride (0.46 g, 13.4 mmol) at 273 K using an ice bath, and then stirred for 0.5 h at the room temperature. After addition of methyl iodide (0.84 ml, 13.4 mol), the reaction mixture was stirred at 313 K for 5 h and cooled to room temperature, adjusted to pH 7 with 1N HCl and then concentrated under reduced pressure. The residue was diluted with ethyl acetate (50 ml), washed with distilled water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, dried in vacuo to give the title compound as a white solid (2.37 g, 95.0%; mp: 380–382 K). Single crystals suitable for X–ray analysis were obtained by slow evaporation of a methanol/water solution (5:1 v/v). ¹H NMR (CDCl₃, δ): 1.34 (s, 3H, CH₃), 1.41 (s, 9H, BOC), 1.46 (s, 9H, BOC), 2.24–2.25 (m, 1H, piperidine), 2.87–2.88 (m, 1H, piperidine), 2.91 (s, 3H, NCH₃), 2.95–3.08 (m, 2H, piperidine), 3.82 (s, 3H, OCH₃), 3.84–3.86 (m, 1H, piperidine), 4.30–4.31 (m, 1H, piperidine); MS (ESI, m/z): 372.2 m/z (M+1)⁺.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1999); 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. The molecular structure of the title compound with the atom–numbering scheme. Displacement ellipsoids are drawn at 40% probability level. H atoms are presented as a small spheres of arbitrary radius.

tert-Butyl 3-[N-(tert-butoxycarbonyl)methylamino]-4-methoxyimino-3- methylpiperidine-1-carboxylate top

Crystal data top

C₁₈H₃₃N₃O₅	F(000) = 1616
M_r = 371.47	D_x = 1.180 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1707 reflections
a = 28.867 (3) Å	θ = 2.7–21.1°
b = 6.1887 (13) Å	µ = 0.09 mm⁻¹
c = 25.379 (3) Å	T = 298 K
β = 112.769 (2)°	Prism, colourless
V = 4180.6 (11) Å³	0.40 × 0.20 × 0.11 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3699 independent reflections
Radiation source: Fine–focus sealed tube	1915 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −33→34
T_min = 0.963, T_max = 0.991	k = −7→6
10032 measured reflections	l = −30→23

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.058P)² + 0.3657P] where P = (F_o² + 2F_c²)/3
3699 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₃₃N₃O₅	V = 4180.6 (11) Å³
M_r = 371.47	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.867 (3) Å	µ = 0.09 mm⁻¹
b = 6.1887 (13) Å	T = 298 K
c = 25.379 (3) Å	0.40 × 0.20 × 0.11 mm
β = 112.769 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3699 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1915 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.991	R_int = 0.060
10032 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.02	Δρ_max = 0.23 e Å⁻³
3699 reflections	Δρ_min = −0.22 e Å⁻³
244 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
N1	0.18007 (8)	0.2543 (3)	0.60235 (9)	0.0389 (6)
N2	0.07900 (7)	0.1687 (4)	0.51326 (9)	0.0367 (6)
N3	0.16321 (7)	−0.1321 (4)	0.47432 (9)	0.0382 (6)
O1	0.16324 (7)	0.3113 (3)	0.67977 (7)	0.0496 (5)
O2	0.21149 (7)	0.5507 (3)	0.65653 (8)	0.0554 (6)
O3	0.07112 (6)	0.1423 (3)	0.42229 (7)	0.0525 (6)
O4	0.01093 (7)	0.3134 (3)	0.44214 (8)	0.0607 (6)
O5	0.19807 (6)	−0.0836 (3)	0.44880 (7)	0.0452 (5)
C1	0.15544 (9)	0.0442 (4)	0.59370 (10)	0.0374 (7)
H1A	0.1361	0.0344	0.6175	0.045*
H1B	0.1809	−0.0681	0.6057	0.045*
C2	0.12010 (9)	0.0043 (4)	0.53070 (10)	0.0335 (6)
C3	0.15423 (9)	0.0354 (4)	0.49846 (10)	0.0325 (6)
C4	0.17891 (10)	0.2510 (4)	0.50509 (11)	0.0387 (7)
H4A	0.1536	0.3625	0.4899	0.046*
H4B	0.2006	0.2542	0.4839	0.046*
C5	0.20975 (10)	0.2938 (5)	0.56825 (11)	0.0459 (8)
H5A	0.2390	0.2005	0.5813	0.055*
H5B	0.2213	0.4425	0.5732	0.055*
C6	0.18713 (10)	0.3856 (5)	0.64739 (11)	0.0399 (7)
C7	0.15940 (11)	0.4430 (5)	0.72637 (12)	0.0495 (8)
C8	0.21026 (13)	0.4764 (6)	0.77309 (13)	0.0738 (11)
H8A	0.2261	0.3388	0.7856	0.111*
H8B	0.2066	0.5494	0.8046	0.111*
H8C	0.2306	0.5623	0.7589	0.111*
C9	0.13357 (14)	0.6544 (6)	0.70277 (15)	0.0871 (13)
H9A	0.1561	0.7461	0.6934	0.131*
H9B	0.1241	0.7241	0.7309	0.131*
H9C	0.1041	0.6272	0.6690	0.131*
C10	0.12728 (14)	0.3024 (6)	0.74676 (14)	0.0903 (13)
H10A	0.0957	0.2762	0.7158	0.135*
H10B	0.1216	0.3738	0.7773	0.135*
H10C	0.1441	0.1674	0.7603	0.135*
C11	0.09808 (10)	−0.2224 (4)	0.52538 (12)	0.0432 (7)
H11A	0.0769	−0.2306	0.5466	0.065*
H11B	0.1248	−0.3256	0.5403	0.065*
H11C	0.0786	−0.2537	0.4859	0.065*
C12	0.05026 (10)	0.2153 (5)	0.45784 (12)	0.0417 (7)
C13	0.05602 (10)	0.2229 (5)	0.55381 (11)	0.0492 (8)
H13A	0.0295	0.3257	0.5367	0.074*
H13B	0.0810	0.2841	0.5877	0.074*
H13C	0.0425	0.0944	0.5636	0.074*
C14	0.04913 (11)	0.1885 (6)	0.36115 (12)	0.0584 (9)
C15	0.04440 (16)	0.4286 (7)	0.35091 (17)	0.1048 (14)
H15A	0.0185	0.4844	0.3620	0.157*
H15B	0.0360	0.4573	0.3111	0.157*
H15C	0.0757	0.4972	0.3731	0.157*
C17	0.08735 (13)	0.0915 (7)	0.34093 (13)	0.0907 (13)
H17A	0.1198	0.1530	0.3622	0.136*
H17B	0.0779	0.1217	0.3010	0.136*
H17C	0.0887	−0.0621	0.3467	0.136*
C16	−0.00059 (12)	0.0715 (7)	0.33491 (14)	0.0906 (13)
H16A	0.0039	−0.0778	0.3460	0.136*
H16B	−0.0129	0.0822	0.2940	0.136*
H16C	−0.0244	0.1360	0.3481	0.136*
C18	0.20473 (11)	−0.2741 (5)	0.42114 (13)	0.0557 (9)
H18A	0.2217	−0.3815	0.4493	0.083*
H18B	0.2245	−0.2411	0.3992	0.083*
H18C	0.1725	−0.3283	0.3962	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0452 (13)	0.0367 (15)	0.0395 (13)	−0.0085 (11)	0.0215 (11)	−0.0060 (12)
N2	0.0359 (12)	0.0426 (15)	0.0368 (13)	0.0076 (11)	0.0198 (11)	0.0002 (11)
N3	0.0368 (12)	0.0427 (15)	0.0420 (13)	0.0011 (11)	0.0226 (11)	−0.0024 (12)
O1	0.0665 (13)	0.0501 (13)	0.0394 (11)	−0.0098 (11)	0.0284 (10)	−0.0081 (10)
O2	0.0687 (14)	0.0486 (14)	0.0528 (13)	−0.0193 (12)	0.0277 (11)	−0.0143 (11)
O3	0.0471 (11)	0.0771 (16)	0.0335 (11)	0.0188 (11)	0.0157 (9)	0.0062 (11)
O4	0.0469 (12)	0.0716 (16)	0.0619 (14)	0.0252 (12)	0.0193 (10)	0.0080 (12)
O5	0.0509 (11)	0.0453 (13)	0.0538 (12)	−0.0003 (10)	0.0360 (10)	−0.0070 (10)
C1	0.0438 (16)	0.0357 (18)	0.0371 (16)	−0.0012 (14)	0.0203 (13)	−0.0006 (13)
C2	0.0361 (15)	0.0331 (17)	0.0349 (15)	0.0017 (13)	0.0178 (12)	0.0011 (13)
C3	0.0314 (14)	0.0359 (17)	0.0331 (15)	0.0034 (13)	0.0155 (12)	0.0006 (13)
C4	0.0451 (16)	0.0350 (17)	0.0442 (17)	−0.0010 (14)	0.0264 (13)	−0.0012 (14)
C5	0.0468 (17)	0.0457 (19)	0.0510 (18)	−0.0088 (15)	0.0254 (15)	−0.0077 (15)
C6	0.0454 (17)	0.0398 (19)	0.0361 (16)	0.0002 (15)	0.0174 (14)	−0.0027 (15)
C7	0.066 (2)	0.050 (2)	0.0392 (17)	0.0003 (17)	0.0280 (16)	−0.0052 (16)
C8	0.090 (3)	0.084 (3)	0.0401 (18)	0.001 (2)	0.0172 (19)	−0.0105 (19)
C9	0.110 (3)	0.089 (3)	0.074 (3)	0.044 (3)	0.049 (2)	0.007 (2)
C10	0.127 (3)	0.099 (3)	0.071 (2)	−0.034 (3)	0.066 (2)	−0.023 (2)
C11	0.0486 (16)	0.0375 (18)	0.0494 (17)	−0.0058 (14)	0.0252 (14)	−0.0037 (15)
C12	0.0406 (17)	0.0440 (19)	0.0439 (18)	0.0051 (15)	0.0201 (14)	0.0005 (15)
C13	0.0461 (17)	0.058 (2)	0.0512 (18)	0.0062 (15)	0.0276 (15)	−0.0066 (16)
C14	0.054 (2)	0.082 (3)	0.0373 (17)	0.0154 (19)	0.0156 (15)	0.0125 (18)
C15	0.120 (3)	0.109 (4)	0.092 (3)	0.012 (3)	0.048 (3)	0.044 (3)
C17	0.079 (2)	0.151 (4)	0.046 (2)	0.030 (3)	0.0297 (19)	0.010 (2)
C16	0.072 (3)	0.130 (4)	0.057 (2)	0.002 (3)	0.0116 (19)	−0.011 (2)
C18	0.065 (2)	0.052 (2)	0.065 (2)	−0.0031 (17)	0.0409 (17)	−0.0190 (17)

Geometric parameters (Å, º) top

N1—C6	1.352 (3)	C8—H8B	0.9600
N1—C5	1.455 (3)	C8—H8C	0.9600
N1—C1	1.457 (3)	C9—H9A	0.9600
N2—C12	1.359 (3)	C9—H9B	0.9600
N2—C13	1.463 (3)	C9—H9C	0.9600
N2—C2	1.494 (3)	C10—H10A	0.9600
N3—C3	1.280 (3)	C10—H10B	0.9600
N3—O5	1.423 (2)	C10—H10C	0.9600
O1—C6	1.342 (3)	C11—H11A	0.9600
O1—C7	1.476 (3)	C11—H11B	0.9600
O2—C6	1.210 (3)	C11—H11C	0.9600
O3—C12	1.342 (3)	C13—H13A	0.9600
O3—C14	1.459 (3)	C13—H13B	0.9600
O4—C12	1.211 (3)	C13—H13C	0.9600
O5—C18	1.423 (3)	C14—C15	1.505 (5)
C1—C2	1.548 (3)	C14—C17	1.510 (4)
C1—H1A	0.9700	C14—C16	1.513 (4)
C1—H1B	0.9700	C15—H15A	0.9600
C2—C3	1.517 (3)	C15—H15B	0.9600
C2—C11	1.525 (3)	C15—H15C	0.9600
C3—C4	1.491 (3)	C17—H17A	0.9600
C4—C5	1.525 (3)	C17—H17B	0.9600
C4—H4A	0.9700	C17—H17C	0.9600
C4—H4B	0.9700	C16—H16A	0.9600
C5—H5A	0.9700	C16—H16B	0.9600
C5—H5B	0.9700	C16—H16C	0.9600
C7—C8	1.502 (4)	C18—H18A	0.9600
C7—C10	1.502 (4)	C18—H18B	0.9600
C7—C9	1.510 (4)	C18—H18C	0.9600
C8—H8A	0.9600

C6—N1—C5	118.1 (2)	C7—C9—H9C	109.5
C6—N1—C1	124.7 (2)	H9A—C9—H9C	109.5
C5—N1—C1	115.2 (2)	H9B—C9—H9C	109.5
C12—N2—C13	114.7 (2)	C7—C10—H10A	109.5
C12—N2—C2	123.2 (2)	C7—C10—H10B	109.5
C13—N2—C2	118.2 (2)	H10A—C10—H10B	109.5
C3—N3—O5	110.9 (2)	C7—C10—H10C	109.5
C6—O1—C7	121.1 (2)	H10A—C10—H10C	109.5
C12—O3—C14	121.7 (2)	H10B—C10—H10C	109.5
C18—O5—N3	107.7 (2)	C2—C11—H11A	109.5
N1—C1—C2	112.7 (2)	C2—C11—H11B	109.5
N1—C1—H1A	109.1	H11A—C11—H11B	109.5
C2—C1—H1A	109.1	C2—C11—H11C	109.5
N1—C1—H1B	109.1	H11A—C11—H11C	109.5
C2—C1—H1B	109.1	H11B—C11—H11C	109.5
H1A—C1—H1B	107.8	O4—C12—O3	123.7 (3)
N2—C2—C3	111.2 (2)	O4—C12—N2	124.5 (3)
N2—C2—C11	110.1 (2)	O3—C12—N2	111.8 (2)
C3—C2—C11	113.9 (2)	N2—C13—H13A	109.5
N2—C2—C1	109.1 (2)	N2—C13—H13B	109.5
C3—C2—C1	103.36 (19)	H13A—C13—H13B	109.5
C11—C2—C1	108.9 (2)	N2—C13—H13C	109.5
N3—C3—C4	127.0 (2)	H13A—C13—H13C	109.5
N3—C3—C2	116.7 (2)	H13B—C13—H13C	109.5
C4—C3—C2	115.7 (2)	O3—C14—C15	110.5 (3)
C3—C4—C5	109.4 (2)	O3—C14—C17	102.1 (2)
C3—C4—H4A	109.8	C15—C14—C17	111.3 (3)
C5—C4—H4A	109.8	O3—C14—C16	108.8 (3)
C3—C4—H4B	109.8	C15—C14—C16	112.9 (3)
C5—C4—H4B	109.8	C17—C14—C16	110.7 (3)
H4A—C4—H4B	108.2	C14—C15—H15A	109.5
N1—C5—C4	110.9 (2)	C14—C15—H15B	109.5
N1—C5—H5A	109.5	H15A—C15—H15B	109.5
C4—C5—H5A	109.5	C14—C15—H15C	109.5
N1—C5—H5B	109.5	H15A—C15—H15C	109.5
C4—C5—H5B	109.5	H15B—C15—H15C	109.5
H5A—C5—H5B	108.0	C14—C17—H17A	109.5
O2—C6—O1	124.7 (3)	C14—C17—H17B	109.5
O2—C6—N1	123.8 (3)	H17A—C17—H17B	109.5
O1—C6—N1	111.5 (3)	C14—C17—H17C	109.5
O1—C7—C8	110.8 (2)	H17A—C17—H17C	109.5
O1—C7—C10	101.8 (2)	H17B—C17—H17C	109.5
C8—C7—C10	110.7 (3)	C14—C16—H16A	109.5
O1—C7—C9	109.8 (2)	C14—C16—H16B	109.5
C8—C7—C9	112.1 (3)	H16A—C16—H16B	109.5
C10—C7—C9	111.3 (3)	C14—C16—H16C	109.5
C7—C8—H8A	109.5	H16A—C16—H16C	109.5
C7—C8—H8B	109.5	H16B—C16—H16C	109.5
H8A—C8—H8B	109.5	O5—C18—H18A	109.5
C7—C8—H8C	109.5	O5—C18—H18B	109.5
H8A—C8—H8C	109.5	H18A—C18—H18B	109.5
H8B—C8—H8C	109.5	O5—C18—H18C	109.5
C7—C9—H9A	109.5	H18A—C18—H18C	109.5
C7—C9—H9B	109.5	H18B—C18—H18C	109.5
H9A—C9—H9B	109.5

C3—N3—O5—C18	−177.9 (2)	C6—N1—C5—C4	−143.2 (2)
C6—N1—C1—C2	139.0 (2)	C1—N1—C5—C4	52.3 (3)
C5—N1—C1—C2	−57.6 (3)	C3—C4—C5—N1	−49.9 (3)
C12—N2—C2—C3	48.3 (3)	C7—O1—C6—O2	8.0 (4)
C13—N2—C2—C3	−155.2 (2)	C7—O1—C6—N1	−171.1 (2)
C12—N2—C2—C11	−78.9 (3)	C5—N1—C6—O2	10.3 (4)
C13—N2—C2—C11	77.7 (3)	C1—N1—C6—O2	173.3 (3)
C12—N2—C2—C1	161.6 (2)	C5—N1—C6—O1	−170.6 (2)
C13—N2—C2—C1	−41.8 (3)	C1—N1—C6—O1	−7.6 (4)
N1—C1—C2—N2	−62.4 (3)	C6—O1—C7—C8	−66.1 (3)
N1—C1—C2—C3	56.0 (3)	C6—O1—C7—C10	176.2 (3)
N1—C1—C2—C11	177.4 (2)	C6—O1—C7—C9	58.3 (3)
O5—N3—C3—C4	−5.2 (3)	C14—O3—C12—O4	4.0 (4)
O5—N3—C3—C2	−176.31 (19)	C14—O3—C12—N2	−175.0 (2)
N2—C2—C3—N3	−129.7 (2)	C13—N2—C12—O4	7.3 (4)
C11—C2—C3—N3	−4.6 (3)	C2—N2—C12—O4	164.6 (3)
C1—C2—C3—N3	113.4 (2)	C13—N2—C12—O3	−173.7 (2)
N2—C2—C3—C4	58.2 (3)	C2—N2—C12—O3	−16.5 (4)
C11—C2—C3—C4	−176.7 (2)	C12—O3—C14—C15	57.0 (4)
C1—C2—C3—C4	−58.8 (3)	C12—O3—C14—C17	175.5 (3)
N3—C3—C4—C5	−113.4 (3)	C12—O3—C14—C16	−67.5 (4)
C2—C3—C4—C5	57.8 (3)

Experimental details

Crystal data
Chemical formula	C₁₈H₃₃N₃O₅
M_r	371.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	28.867 (3), 6.1887 (13), 25.379 (3)
β (°)	112.769 (2)
V (Å³)	4180.6 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.20 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.963, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	10032, 3699, 1915
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.144, 1.02
No. of reflections	3699
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.22

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the IMB Research Foundation.

References

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