12-Nitro­methyl-14-deoxy­andro­graph­olide

Quan, J.-C.; Chen, J.; Xu, H.; Hu, C.-H.; Wang, J.-T.

doi:10.1107/S1600536808018746

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1343

doi:10.1107/S1600536808018746

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12-Nitromethyl-14-deoxyandrographolide

Ji-Cai Quan,^a Jing Chen,^a ^* Hao Xu,^a Chen-Hui Hu ^a and Jin-Tang Wang ^a

^aCollege of Science, Nanjing University of Technology, Xinmofan Road No. 5, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: cj1908@126.com

(Received 19 June 2008; accepted 20 June 2008; online 28 June 2008)

In the molecule of the title compound {systematic name: 3-[2-(6-hydroxy-5-hydroxymethyl-5,8a-dimethyl-2-methyleneperhydro-1-napthyl)-1-(nitromethyl)ethyl]-2(4H)-furanone}, C₂₁H₃₁NO₆, the cyclohexane rings have chair conformations. Intramolecular O—H⋯O hydrogen bonding results in the formation of a six-membered non-planar ring with a twist conformation. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into infinite chains along the c axis.

Related literature

For bond-length data, see: Allen et al. (1987 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₁H₃₁NO₆
M_r = 393.47
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.503 (2) Å
b = 13.151 (3) Å
c = 13.434 (3) Å
V = 2032.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 (2) K
0.40 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.964, T_max = 0.982
3993 measured reflections
3643 independent reflections
2711 reflections with I > 2σ(I)
R_int = 0.032
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.188
S = 0.98
3643 reflections
256 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.82	2.08	2.751 (5)	139
O2—H2A⋯O3ⁱ	0.85 (4)	2.11 (4)	2.906 (5)	156 (4)
Symmetry code: (i) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018746/hk2476sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018746/hk2476Isup2.hkl

checkCIF report

Comment top

Some derivatives of andrographolide are important chemical materials. We report herein the crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C2-C7) and B (C5/C6/C8-C11) adopt chair [ϕ = -86.32 (2)° and θ = 4.69 (3)° (for ring A) and ϕ = -148.49 (3)° and θ = 86.21 (3)° (for ring B)] conformations, having total puckering amplitudes, Q_T, of 0.606 (3) Å and 0.642 (3) Å, respectively (Cremer & Pople, 1975). Ring C (O4/C18-C21) is, of course, planar. The intramolecular O-H···O hydrogen bond (Table 1) results in the formation of a six-membered non-planar ring: D (O1/H1A/O2/C8/C9/C13), in which it adopts twisted conformation, having total puckering amplitude, Q_T, of 1.200 (3) Å (Cremer & Pople, 1975).

In the crystal structure, intermolecular O-H···O hydrogen bonds (Table 1) link the molecules into infinite chains along the c axis (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For bond-length data, see: Allen et al. (1987). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

For the preparation of the title compound, andrographolide (10 g) was dissolved in methanol (40 ml), and then nitromethane (16 ml), methanol (32 ml) and sodium methoxide (4.2 g) were added by stirring at room temperature. The reaction mixture was poured into ice salt water (120 ml). After the reaction finished, it was extracted with ethyl acetate, washed with saturated salt water and dryed with sodium sulfate. The product was filtrated and the organic layer was concentrated. Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution.

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bond is shown as dashed line.
	Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

3-[2-(6-hydroxy-5-hydroxymethyl-5,8a-dimethyl-2-methyleneperhydro- 1-napthyl)-1-(nitromethyl)ethyl]-2(4H)-furanone top

Crystal data top

C₂₁H₃₁NO₆	F(000) = 848
M_r = 393.47	D_x = 1.289 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 11.503 (2) Å	θ = 10–13°
b = 13.151 (3) Å	µ = 0.09 mm⁻¹
c = 13.434 (3) Å	T = 294 K
V = 2032.2 (7) Å³	Block, colorless
Z = 4	0.40 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2711 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 25.2°, θ_min = 2.2°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
T_min = 0.964, T_max = 0.982	l = −16→16
3993 measured reflections	3 standard reflections every 120 min
3643 independent reflections	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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.1P)² + 1.5P] where P = (F_o² + 2F_c²)/3
3643 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₁H₃₁NO₆	V = 2032.2 (7) Å³
M_r = 393.47	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.503 (2) Å	µ = 0.09 mm⁻¹
b = 13.151 (3) Å	T = 294 K
c = 13.434 (3) Å	0.40 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2711 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.032
T_min = 0.964, T_max = 0.982	3 standard reflections every 120 min
3993 measured reflections	intensity decay: 1%
3643 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	1 restraint
wR(F²) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.19 e Å⁻³
3643 reflections	Δρ_min = −0.20 e Å⁻³
256 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 > 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
O1	0.3022 (3)	0.2945 (3)	0.3635 (3)	0.0757 (11)
H1A	0.3210	0.2868	0.4219	0.114*
O2	0.4711 (3)	0.2805 (3)	0.5078 (2)	0.0664 (9)
H2A	0.477 (5)	0.325 (3)	0.553 (3)	0.080*
O3	0.9911 (4)	0.6195 (2)	0.1980 (3)	0.0767 (11)
O4	1.0518 (4)	0.5831 (2)	0.3513 (2)	0.0705 (10)
O5	1.2868 (3)	0.3264 (4)	0.0613 (3)	0.0923 (14)
O6	1.2176 (3)	0.4675 (3)	0.1109 (3)	0.0743 (11)
N	1.2092 (3)	0.3771 (4)	0.0954 (3)	0.0557 (10)
C1	0.7547 (4)	0.4347 (4)	0.0088 (3)	0.0629 (13)
H1B	0.7162	0.4713	−0.0404	0.075*
H1C	0.8097	0.3861	−0.0088	0.075*
C2	0.7313 (4)	0.4515 (3)	0.1031 (3)	0.0448 (10)
C3	0.6437 (4)	0.5286 (3)	0.1353 (4)	0.0522 (11)
H3A	0.6129	0.5636	0.0775	0.063*
H3B	0.6806	0.5786	0.1780	0.063*
C4	0.5440 (4)	0.4763 (3)	0.1922 (3)	0.0488 (11)
H4A	0.4909	0.5274	0.2175	0.059*
H4B	0.5011	0.4326	0.1470	0.059*
C5	0.5913 (3)	0.4130 (3)	0.2788 (3)	0.0344 (8)
H5A	0.6378	0.4615	0.3172	0.041*
C6	0.6812 (3)	0.3322 (3)	0.2437 (3)	0.0331 (8)
C7	0.7821 (3)	0.3923 (3)	0.1901 (3)	0.0359 (8)
H7A	0.8088	0.4433	0.2380	0.043*
C8	0.4951 (3)	0.3781 (3)	0.3532 (3)	0.0407 (9)
C9	0.5559 (4)	0.3237 (4)	0.4396 (3)	0.0500 (10)
H9A	0.6021	0.3740	0.4761	0.060*
C10	0.6359 (4)	0.2395 (3)	0.4063 (3)	0.0496 (11)
H10A	0.5908	0.1876	0.3725	0.059*
H10B	0.6717	0.2085	0.4642	0.059*
C11	0.7308 (3)	0.2784 (3)	0.3364 (3)	0.0445 (10)
H11A	0.7786	0.2216	0.3153	0.053*
H11B	0.7802	0.3255	0.3724	0.053*
C12	0.4332 (5)	0.4722 (4)	0.3948 (4)	0.0646 (13)
H12A	0.3736	0.4513	0.4405	0.097*
H12B	0.3988	0.5098	0.3411	0.097*
H12C	0.4884	0.5144	0.4289	0.097*
C13	0.4032 (3)	0.3085 (4)	0.3047 (4)	0.0519 (11)
H13A	0.3806	0.3375	0.2412	0.062*
H13B	0.4380	0.2427	0.2917	0.062*
C14	0.6321 (4)	0.2524 (3)	0.1714 (3)	0.0465 (10)
H14A	0.5702	0.2157	0.2032	0.070*
H14B	0.6925	0.2058	0.1527	0.070*
H14C	0.6027	0.2857	0.1130	0.070*
C15	0.8890 (3)	0.3280 (3)	0.1645 (3)	0.0422 (9)
H15A	0.8742	0.2914	0.1031	0.051*
H15B	0.9011	0.2783	0.2167	0.051*
C16	1.0006 (3)	0.3920 (3)	0.1522 (3)	0.0392 (9)
H16A	0.9876	0.4425	0.0998	0.047*
C17	1.0987 (4)	0.3222 (4)	0.1201 (4)	0.0555 (12)
H17A	1.1141	0.2739	0.1731	0.067*
H17B	1.0738	0.2839	0.0621	0.067*
C18	1.0289 (3)	0.4467 (3)	0.2473 (3)	0.0400 (9)
C19	1.0200 (4)	0.5570 (4)	0.2574 (3)	0.0534 (11)
C20	1.0817 (5)	0.4937 (4)	0.4047 (4)	0.0668 (13)
H20A	1.0320	0.4855	0.4625	0.080*
H20B	1.1620	0.4965	0.4268	0.080*
C21	1.0646 (4)	0.4099 (4)	0.3342 (3)	0.0523 (11)
H21A	1.0769	0.3415	0.3481	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0430 (18)	0.083 (2)	0.101 (3)	−0.0086 (17)	0.0210 (19)	0.002 (2)
O2	0.069 (2)	0.081 (2)	0.0489 (18)	−0.007 (2)	0.0189 (17)	0.0045 (16)
O3	0.112 (3)	0.0437 (17)	0.075 (2)	0.001 (2)	−0.020 (2)	0.0099 (17)
O4	0.094 (3)	0.061 (2)	0.0572 (19)	−0.0127 (19)	−0.0167 (19)	−0.0096 (17)
O5	0.055 (2)	0.131 (4)	0.091 (3)	0.000 (2)	0.018 (2)	−0.038 (3)
O6	0.050 (2)	0.078 (3)	0.095 (3)	−0.0172 (18)	0.0090 (19)	0.015 (2)
N	0.038 (2)	0.089 (3)	0.0404 (19)	0.000 (2)	0.0067 (16)	−0.003 (2)
C1	0.054 (3)	0.080 (3)	0.055 (3)	−0.012 (3)	0.001 (2)	0.014 (3)
C2	0.041 (2)	0.047 (2)	0.047 (2)	−0.0133 (19)	0.0018 (18)	0.0099 (19)
C3	0.052 (3)	0.044 (2)	0.061 (3)	0.002 (2)	−0.005 (2)	0.015 (2)
C4	0.044 (2)	0.048 (2)	0.055 (3)	0.0084 (19)	−0.001 (2)	0.016 (2)
C5	0.0328 (19)	0.0331 (19)	0.0373 (19)	−0.0008 (15)	−0.0054 (15)	−0.0029 (15)
C6	0.0341 (19)	0.0299 (18)	0.0353 (19)	−0.0043 (16)	−0.0006 (16)	−0.0001 (16)
C7	0.0347 (19)	0.0321 (18)	0.041 (2)	−0.0026 (17)	−0.0040 (17)	−0.0023 (16)
C8	0.037 (2)	0.0405 (19)	0.045 (2)	0.0007 (18)	0.0087 (18)	−0.0034 (17)
C9	0.054 (2)	0.058 (3)	0.038 (2)	−0.012 (2)	0.0076 (19)	−0.0002 (19)
C10	0.051 (3)	0.056 (2)	0.042 (2)	0.004 (2)	−0.004 (2)	0.018 (2)
C11	0.041 (2)	0.043 (2)	0.049 (2)	0.0014 (18)	0.0008 (19)	0.0079 (18)
C12	0.064 (3)	0.058 (3)	0.072 (3)	0.006 (2)	0.017 (3)	−0.006 (2)
C13	0.036 (2)	0.056 (3)	0.064 (3)	−0.003 (2)	0.004 (2)	0.008 (2)
C14	0.051 (2)	0.039 (2)	0.049 (2)	−0.0112 (19)	0.007 (2)	−0.0069 (19)
C15	0.040 (2)	0.0364 (19)	0.050 (2)	−0.0072 (17)	0.0065 (18)	−0.0022 (17)
C16	0.038 (2)	0.0405 (19)	0.039 (2)	−0.0032 (18)	0.0041 (17)	0.0026 (17)
C17	0.041 (2)	0.065 (3)	0.061 (3)	−0.005 (2)	0.011 (2)	−0.009 (2)
C18	0.033 (2)	0.044 (2)	0.043 (2)	−0.0048 (17)	−0.0007 (18)	0.0054 (18)
C19	0.058 (3)	0.049 (2)	0.053 (2)	−0.008 (2)	−0.005 (2)	−0.001 (2)
C20	0.065 (3)	0.087 (4)	0.048 (3)	−0.009 (3)	−0.007 (2)	0.004 (3)
C21	0.048 (2)	0.058 (3)	0.050 (2)	−0.001 (2)	−0.004 (2)	0.011 (2)

Geometric parameters (Å, º) top

O1—C13	1.417 (5)	C8—C13	1.542 (6)
O1—H1A	0.8200	C9—C10	1.509 (6)
O2—C9	1.453 (5)	C9—H9A	0.9800
O2—H2A	0.85 (4)	C10—C11	1.528 (6)
O3—C19	1.194 (5)	C10—H10A	0.9700
C3—C4	1.540 (6)	C10—H10B	0.9700
C3—H3A	0.9700	C11—H11A	0.9700
C3—H3B	0.9700	C11—H11B	0.9700
O4—C19	1.358 (5)	C12—H12A	0.9600
O4—C20	1.420 (6)	C12—H12B	0.9600
N—O5	1.205 (5)	C12—H12C	0.9600
N—O6	1.211 (5)	C13—H13A	0.9700
N—C17	1.499 (6)	C13—H13B	0.9700
C1—C2	1.314 (6)	C14—H14A	0.9600
C1—H1B	0.9300	C14—H14B	0.9600
C1—H1C	0.9300	C14—H14C	0.9600
C2—C3	1.494 (6)	C15—C16	1.544 (5)
C2—C7	1.521 (6)	C15—H15A	0.9700
C4—C5	1.530 (5)	C15—H15B	0.9700
C4—H4A	0.9700	C16—C18	1.502 (6)
C4—H4B	0.9700	C16—C17	1.517 (6)
C5—C6	1.556 (5)	C16—H16A	0.9800
C5—C8	1.561 (5)	C17—H17A	0.9700
C5—H5A	0.9800	C17—H17B	0.9700
C6—C14	1.538 (5)	C18—C21	1.329 (6)
C6—C11	1.542 (5)	C18—C19	1.460 (6)
C6—C7	1.578 (5)	C20—C21	1.467 (7)
C7—C15	1.531 (5)	C20—H20A	0.9700
C7—H7A	0.9800	C20—H20B	0.9700
C8—C9	1.532 (6)	C21—H21A	0.9300
C8—C12	1.533 (6)

C13—O1—H1A	109.5	H10A—C10—H10B	107.9
O5—N—O6	123.3 (4)	C10—C11—C6	112.7 (3)
O5—N—C17	116.5 (4)	C10—C11—H11A	109.1
O6—N—C17	120.2 (4)	C6—C11—H11A	109.1
C2—C1—H1B	120.0	C10—C11—H11B	109.1
C2—C1—H1C	120.0	C6—C11—H11B	109.1
H1B—C1—H1C	120.0	H11A—C11—H11B	107.8
C1—C2—C3	122.1 (4)	C8—C12—H12A	109.5
C1—C2—C7	125.2 (4)	C8—C12—H12B	109.5
C3—C2—C7	112.6 (3)	H12A—C12—H12B	109.5
C9—O2—H2A	97 (4)	C8—C12—H12C	109.5
C2—C3—C4	110.1 (3)	H12A—C12—H12C	109.5
C2—C3—H3A	109.6	H12B—C12—H12C	109.5
C4—C3—H3A	109.6	O1—C13—C8	113.8 (4)
C2—C3—H3B	109.6	O1—C13—H13A	108.8
C4—C3—H3B	109.7	C8—C13—H13A	108.8
H3A—C3—H3B	108.2	O1—C13—H13B	108.8
C19—O4—C20	109.0 (4)	C8—C13—H13B	108.8
C5—C4—C3	110.8 (3)	H13A—C13—H13B	107.7
C5—C4—H4A	109.5	C6—C14—H14A	109.5
C3—C4—H4A	109.5	C6—C14—H14B	109.5
C5—C4—H4B	109.5	H14A—C14—H14B	109.5
C3—C4—H4B	109.5	C6—C14—H14C	109.5
H4A—C4—H4B	108.1	H14A—C14—H14C	109.5
C4—C5—C6	112.2 (3)	H14B—C14—H14C	109.5
C4—C5—C8	113.3 (3)	C7—C15—C16	113.1 (3)
C6—C5—C8	117.7 (3)	C7—C15—H15A	109.0
C4—C5—H5A	103.9	C16—C15—H15A	109.0
C6—C5—H5A	103.9	C7—C15—H15B	109.0
C8—C5—H5A	103.9	C16—C15—H15B	109.0
C14—C6—C11	109.5 (3)	H15A—C15—H15B	107.8
C14—C6—C5	114.4 (3)	C18—C16—C17	111.8 (4)
C11—C6—C5	108.3 (3)	C18—C16—C15	110.6 (3)
C14—C6—C7	108.9 (3)	C17—C16—C15	108.6 (3)
C11—C6—C7	109.0 (3)	C18—C16—H16A	108.6
C5—C6—C7	106.6 (3)	C17—C16—H16A	108.6
C2—C7—C15	114.7 (3)	C15—C16—H16A	108.6
C2—C7—C6	108.9 (3)	N—C17—C16	113.7 (4)
C15—C7—C6	114.7 (3)	N—C17—H17A	108.8
C2—C7—H7A	105.9	C16—C17—H17A	108.8
C15—C7—H7A	105.9	N—C17—H17B	108.8
C6—C7—H7A	105.9	C16—C17—H17B	108.8
C9—C8—C12	108.2 (4)	H17A—C17—H17B	107.7
C9—C8—C13	110.9 (3)	C21—C18—C19	107.6 (4)
C12—C8—C13	108.3 (4)	C21—C18—C16	129.7 (4)
C9—C8—C5	107.4 (3)	C19—C18—C16	122.7 (4)
C12—C8—C5	109.0 (3)	O3—C19—O4	121.5 (4)
C13—C8—C5	112.9 (3)	O3—C19—C18	129.9 (4)
O2—C9—C10	108.0 (4)	O4—C19—C18	108.6 (4)
O2—C9—C8	110.7 (4)	O4—C20—C21	105.2 (4)
C10—C9—C8	113.3 (3)	O4—C20—H20A	110.7
O2—C9—H9A	108.2	C21—C20—H20A	110.7
C10—C9—H9A	108.2	O4—C20—H20B	110.7
C8—C9—H9A	108.2	C21—C20—H20B	110.7
C9—C10—C11	111.9 (3)	H20A—C20—H20B	108.8
C9—C10—H10A	109.2	C18—C21—C20	109.6 (4)
C11—C10—H10A	109.2	C18—C21—H21A	125.2
C9—C10—H10B	109.2	C20—C21—H21A	125.2
C11—C10—H10B	109.2

C1—C2—C3—C4	117.9 (5)	C5—C8—C9—C10	−53.2 (4)
C7—C2—C3—C4	−58.4 (5)	O2—C9—C10—C11	−178.3 (3)
C2—C3—C4—C5	54.5 (5)	C8—C9—C10—C11	58.7 (5)
C3—C4—C5—C6	−56.8 (4)	C9—C10—C11—C6	−57.0 (5)
C3—C4—C5—C8	167.0 (3)	C14—C6—C11—C10	−74.5 (4)
C4—C5—C6—C14	−62.0 (4)	C5—C6—C11—C10	50.8 (4)
C8—C5—C6—C14	72.1 (4)	C7—C6—C11—C10	166.4 (3)
C4—C5—C6—C11	175.6 (3)	C9—C8—C13—O1	72.8 (4)
C8—C5—C6—C11	−50.3 (4)	C12—C8—C13—O1	−45.8 (5)
C4—C5—C6—C7	58.4 (4)	C5—C8—C13—O1	−166.6 (4)
C8—C5—C6—C7	−167.5 (3)	C2—C7—C15—C16	75.8 (4)
C1—C2—C7—C15	15.6 (6)	C6—C7—C15—C16	−157.0 (3)
C3—C2—C7—C15	−168.2 (3)	C7—C15—C16—C18	60.9 (4)
C1—C2—C7—C6	−114.4 (5)	C7—C15—C16—C17	−176.2 (4)
C3—C2—C7—C6	61.8 (4)	O5—N—C17—C16	−173.8 (4)
C14—C6—C7—C2	64.7 (4)	O6—N—C17—C16	6.9 (6)
C11—C6—C7—C2	−175.9 (3)	C18—C16—C17—N	−63.8 (5)
C5—C6—C7—C2	−59.2 (4)	C15—C16—C17—N	174.0 (4)
C14—C6—C7—C15	−65.3 (4)	C17—C16—C18—C21	−52.3 (6)
C11—C6—C7—C15	54.1 (4)	C15—C16—C18—C21	68.9 (5)
C5—C6—C7—C15	170.8 (3)	C17—C16—C18—C19	127.8 (4)
C4—C5—C8—C9	−175.4 (3)	C15—C16—C18—C19	−111.0 (4)
C6—C5—C8—C9	51.0 (4)	C20—O4—C19—O3	−179.9 (5)
C4—C5—C8—C12	−58.4 (5)	C20—O4—C19—C18	−0.1 (5)
C6—C5—C8—C12	168.0 (4)	C21—C18—C19—O3	−179.8 (5)
C4—C5—C8—C13	62.1 (4)	C16—C18—C19—O3	0.1 (8)
C6—C5—C8—C13	−71.5 (4)	C21—C18—C19—O4	0.4 (5)
C12—C8—C9—O2	67.8 (4)	C16—C18—C19—O4	−179.7 (3)
C13—C8—C9—O2	−50.9 (4)	C19—O4—C20—C21	−0.2 (5)
C5—C8—C9—O2	−174.7 (3)	C19—C18—C21—C20	−0.5 (5)
C12—C8—C9—C10	−170.7 (4)	C16—C18—C21—C20	179.6 (4)
C13—C8—C9—C10	70.6 (4)	O4—C20—C21—C18	0.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	2.08	2.751 (5)	139
O2—H2A···O3ⁱ	0.85 (4)	2.11 (4)	2.906 (5)	156 (4)

Symmetry code: (i) −x+3/2, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₃₁NO₆
M_r	393.47
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	294
a, b, c (Å)	11.503 (2), 13.151 (3), 13.434 (3)
V (Å³)	2032.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.964, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	3993, 3643, 2711
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.188, 0.98
No. of reflections	3643
No. of parameters	256
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	2.08	2.751 (5)	139.00
O2—H2A···O3ⁱ	0.85 (4)	2.11 (4)	2.906 (5)	156 (4)

Symmetry code: (i) −x+3/2, −y+1, z+1/2.

Acknowledgements

The authors thank the Center for Testing and Analysis, Nanjing University, for support.

References

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Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar