Dihydro­cryptopine

Sun, W.; Cao, L.; Zhang, C.; Zhu, L.; Zhou, L.

doi:10.1107/S1600536812017588

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1762

doi:10.1107/S1600536812017588

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Dihydrocryptopine

Wenwen Sun,^a Lei Cao,^a Cen Zhang,^a Lifei Zhu ^a and Le Zhou ^a ^*

^aCollege of Science, Northwest Agriculture and Forestry University, Yangling 712100, People's Republic of China
^*Correspondence e-mail: zhoulechem@yahoo.com.cn

(Received 7 March 2012; accepted 20 April 2012; online 16 May 2012)

In the crystal structure of the title compound [systematic name: 6,7-dimethoxy-12-methyl-16,18-dioxa-12-azatetracyclo[12.7.0.0^4,9.0^15,19]henicosa-1(21),4,6,8,14,19-hexaen-3-ol], C₂₁H₂₅NO₅, the benzene rings exhibits a dihedral angle of 14.95 (4)°. In the crystal, molecules are linked by pairs of O—H⋯O hydrogen bonding into inversion dimers. These dimers are further connected by C—H⋯O interactions.

Related literature

For the synthesis of the title compound, see: Wada et al. (2007 ). For the biological activity of cryptopine derivatives, see: Morteza et al. (2003 ); Yang et al. (2009 ); Capasso et al. (1997 ); Jeong et al. (2009 ).

Experimental

Crystal data

C₂₁H₂₅NO₅
M_r = 371.42
Monoclinic, P 2₁ /c
a = 9.5810 (16) Å
b = 6.7405 (12) Å
c = 28.886 (5) Å
β = 92.164 (2)°
V = 1864.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.26 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.976, T_max = 0.983
13267 measured reflections
3460 independent reflections
2721 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.02
3460 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4ⁱ	0.82	2.31	3.0924 (16)	159
C1—H1A⋯O3ⁱⁱ	0.97	2.41	3.367 (2)	170
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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/S1600536812017588/nc2270sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017588/nc2270Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812017588/nc2270Isup3.cml

checkCIF report

Comment top

The cryptopine derivatives have recently attracted great attention due to their antifungal (Morteza et al. 2003) and antibacterial activity (Yang et al. 2009), their analgesic effect (Capasso et al. 1997) and anti-dementia prperties (Jeong et al. 2009). In this context we are interested in the synthesis of cryptopine derivatives with biological activity. Within this project the crystal structure of the title compound was determined.

The molecule of the title compound is characterized by the presence of a ten-membered ring (hexahydrodibenzo[c,g]azecine) with a methylated tertiary nitrogen atom and a hydroxyl group fused to two aryl moieties (Fig. 1). In general, the title compound have two oxygenated substituents on the benzene ring and two methoxyl on the other benzene ring.Benzene rings C2/C3/C4/C5/C6/C7 and C11/C12/C16/C17/C18/C19 are inclined with respect to one another with a dihedral angle of 19.949 (41)°.

In the crystal structure, two adjacent molecules are linked by intermolecular O—H···O hydrogen bond into centrosymmetrically dimers that are further connected into layers by weak C—H···O interactions (Table 1).

Related literature top

For the synthesis of the title compound, see: Wada et al. (2007). For the biological activity of cryptopine derivatives, see: Morteza et al. (2003); Yang et al. (2009); Capasso et al. (1997); Jeong et al. (2009).

Experimental top

The title compound was synthesized according to the literature procedure (Wada et al. 2007), and crystals were obtained from a solution in methanol by slow evaporation of the solvent at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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. ORTEP drawing of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level.

6,7-dimethoxy-12-methyl-16,18-dioxa-12- azatetracyclo[12.7.0.0^4,9.0^15,19]henicosa-1(21),4,6,8,14,19-hexaen-3-ol top

Crystal data top

C₂₁H₂₅NO₅	F(000) = 792
M_r = 371.42	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5810 (16) Å	Cell parameters from 4124 reflections
b = 6.7405 (12) Å	θ = 2.5–26.5°
c = 28.886 (5) Å	µ = 0.09 mm⁻¹
β = 92.164 (2)°	T = 296 K
V = 1864.2 (6) Å³	Block, colourless
Z = 4	0.26 × 0.21 × 0.18 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3460 independent reflections
Radiation source: fine-focus sealed tube	2721 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
phi and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.976, T_max = 0.983	k = −8→8
13267 measured reflections	l = −34→34

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0533P)² + 0.3327P] where P = (F_o² + 2F_c²)/3
3460 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₁H₂₅NO₅	V = 1864.2 (6) Å³
M_r = 371.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5810 (16) Å	µ = 0.09 mm⁻¹
b = 6.7405 (12) Å	T = 296 K
c = 28.886 (5) Å	0.26 × 0.21 × 0.18 mm
β = 92.164 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3460 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2721 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.983	R_int = 0.021
13267 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	Δρ_max = 0.12 e Å⁻³
3460 reflections	Δρ_min = −0.18 e Å⁻³
248 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	0.7221 (2)	0.5338 (3)	0.34220 (6)	0.0678 (5)
H1A	0.6576	0.6282	0.3550	0.081*
H1B	0.8016	0.5203	0.3638	0.081*
C2	0.72327 (15)	0.4630 (2)	0.26692 (5)	0.0479 (4)
C3	0.65789 (15)	0.3100 (3)	0.28885 (5)	0.0487 (4)
C4	0.60582 (15)	0.1506 (2)	0.26509 (5)	0.0487 (4)
H4	0.5641	0.0445	0.2798	0.058*
C5	0.61899 (14)	0.1562 (2)	0.21705 (5)	0.0422 (3)
H5	0.5837	0.0503	0.1996	0.051*
C6	0.68174 (13)	0.3111 (2)	0.19394 (5)	0.0377 (3)
C7	0.73928 (15)	0.4729 (2)	0.21985 (5)	0.0431 (3)
C8	0.80651 (18)	0.6541 (2)	0.19944 (5)	0.0548 (4)
H8A	0.7337	0.7419	0.1873	0.066*
H8B	0.8579	0.7244	0.2239	0.066*
C9	0.92335 (19)	0.7795 (2)	0.13244 (6)	0.0612 (5)
H9A	1.0044	0.7549	0.1141	0.073*
H9B	0.9429	0.8954	0.1515	0.073*
C10	0.79804 (19)	0.8230 (2)	0.09997 (6)	0.0576 (4)
H10A	0.7165	0.8392	0.1185	0.069*
H10B	0.8141	0.9485	0.0846	0.069*
C11	0.76530 (15)	0.6684 (2)	0.06336 (5)	0.0446 (4)
C12	0.67469 (14)	0.5083 (2)	0.06902 (5)	0.0410 (3)
C13	0.60773 (14)	0.4639 (2)	0.11475 (5)	0.0411 (3)
H13	0.6067	0.5852	0.1334	0.049*
C14	0.68894 (14)	0.3028 (2)	0.14177 (4)	0.0390 (3)
H14A	0.6543	0.1744	0.1314	0.047*
H14B	0.7863	0.3110	0.1338	0.047*
C15	1.03219 (19)	0.5291 (4)	0.18198 (7)	0.0806 (6)
H15A	1.0963	0.5089	0.1577	0.121*
H15B	1.0145	0.4048	0.1969	0.121*
H15C	1.0718	0.6208	0.2042	0.121*
C16	0.64789 (15)	0.3799 (2)	0.03173 (5)	0.0435 (3)
H16	0.5874	0.2737	0.0354	0.052*
C17	0.70861 (15)	0.4061 (2)	−0.01042 (5)	0.0450 (4)
C18	0.80076 (15)	0.5652 (2)	−0.01613 (5)	0.0462 (4)
C19	0.82693 (16)	0.6915 (2)	0.02052 (5)	0.0490 (4)
H19	0.8882	0.7967	0.0167	0.059*
C20	0.5989 (2)	0.1198 (3)	−0.04403 (6)	0.0634 (5)
H20A	0.6408	0.0319	−0.0214	0.095*
H20B	0.5888	0.0524	−0.0732	0.095*
H20C	0.5087	0.1606	−0.0342	0.095*
C21	0.95733 (18)	0.7328 (3)	−0.06464 (6)	0.0669 (5)
H21A	0.9147	0.8601	−0.0605	0.100*
H21B	0.9929	0.7246	−0.0952	0.100*
H21C	1.0326	0.7159	−0.0421	0.100*
N1	0.90152 (13)	0.60922 (19)	0.16244 (4)	0.0504 (3)
O1	0.76747 (15)	0.6038 (2)	0.29889 (4)	0.0766 (4)
O2	0.65523 (14)	0.3471 (2)	0.33582 (4)	0.0720 (4)
O3	0.46774 (10)	0.39104 (16)	0.10842 (4)	0.0531 (3)
H3	0.4165	0.4813	0.0992	0.080*
O4	0.68526 (12)	0.28907 (18)	−0.04891 (3)	0.0598 (3)
O5	0.85638 (11)	0.58148 (19)	−0.05891 (4)	0.0626 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0611 (11)	0.0995 (15)	0.0425 (9)	0.0074 (10)	0.0007 (8)	−0.0176 (9)
C2	0.0436 (8)	0.0566 (9)	0.0436 (8)	0.0013 (7)	0.0005 (6)	−0.0111 (7)
C3	0.0411 (8)	0.0690 (10)	0.0361 (8)	0.0084 (8)	0.0029 (6)	0.0023 (7)
C4	0.0416 (8)	0.0584 (10)	0.0463 (9)	0.0007 (7)	0.0048 (6)	0.0102 (7)
C5	0.0381 (7)	0.0437 (8)	0.0448 (8)	0.0007 (6)	0.0017 (6)	−0.0003 (6)
C6	0.0329 (7)	0.0396 (8)	0.0409 (7)	0.0039 (6)	0.0043 (6)	−0.0019 (6)
C7	0.0400 (8)	0.0468 (8)	0.0430 (8)	0.0008 (6)	0.0057 (6)	−0.0055 (6)
C8	0.0655 (10)	0.0488 (9)	0.0507 (9)	−0.0124 (8)	0.0105 (8)	−0.0138 (7)
C9	0.0698 (11)	0.0517 (10)	0.0631 (11)	−0.0270 (9)	0.0159 (9)	−0.0119 (8)
C10	0.0734 (11)	0.0354 (8)	0.0653 (10)	−0.0082 (8)	0.0201 (9)	0.0018 (7)
C11	0.0473 (8)	0.0383 (8)	0.0488 (8)	0.0014 (6)	0.0082 (7)	0.0079 (6)
C12	0.0406 (8)	0.0402 (8)	0.0425 (8)	0.0027 (6)	0.0071 (6)	0.0061 (6)
C13	0.0421 (8)	0.0388 (8)	0.0431 (8)	−0.0021 (6)	0.0090 (6)	0.0005 (6)
C14	0.0413 (8)	0.0360 (7)	0.0403 (8)	−0.0014 (6)	0.0076 (6)	−0.0042 (6)
C15	0.0506 (11)	0.1104 (17)	0.0806 (14)	−0.0113 (11)	−0.0011 (9)	0.0008 (12)
C16	0.0426 (8)	0.0462 (8)	0.0420 (8)	−0.0050 (6)	0.0053 (6)	0.0063 (6)
C17	0.0411 (8)	0.0558 (9)	0.0381 (8)	0.0007 (7)	0.0018 (6)	0.0054 (7)
C18	0.0405 (8)	0.0589 (10)	0.0396 (8)	−0.0001 (7)	0.0062 (6)	0.0131 (7)
C19	0.0458 (8)	0.0465 (9)	0.0553 (9)	−0.0043 (7)	0.0082 (7)	0.0147 (7)
C20	0.0755 (12)	0.0650 (11)	0.0500 (10)	−0.0126 (9)	0.0076 (8)	−0.0057 (8)
C21	0.0538 (10)	0.0878 (13)	0.0600 (10)	−0.0096 (9)	0.0150 (8)	0.0255 (10)
N1	0.0459 (7)	0.0517 (8)	0.0541 (8)	−0.0122 (6)	0.0078 (6)	−0.0070 (6)
O1	0.0940 (10)	0.0879 (9)	0.0483 (7)	−0.0248 (8)	0.0078 (6)	−0.0235 (6)
O2	0.0812 (9)	0.0981 (10)	0.0369 (6)	−0.0062 (8)	0.0049 (6)	−0.0039 (6)
O3	0.0399 (6)	0.0642 (7)	0.0555 (7)	−0.0020 (5)	0.0074 (5)	0.0149 (5)
O4	0.0663 (7)	0.0753 (8)	0.0382 (6)	−0.0172 (6)	0.0086 (5)	−0.0013 (5)
O5	0.0566 (7)	0.0870 (9)	0.0451 (6)	−0.0144 (6)	0.0139 (5)	0.0140 (6)

Geometric parameters (Å, º) top

C1—O1	1.420 (2)	C12—C16	1.398 (2)
C1—O2	1.422 (2)	C12—C13	1.5200 (19)
C1—H1A	0.9700	C13—O3	1.4335 (17)
C1—H1B	0.9700	C13—C14	1.5322 (19)
C2—C3	1.374 (2)	C13—H13	0.9800
C2—C7	1.376 (2)	C14—H14A	0.9700
C2—O1	1.3793 (18)	C14—H14B	0.9700
C3—C4	1.360 (2)	C15—N1	1.457 (2)
C3—O2	1.3807 (17)	C15—H15A	0.9600
C4—C5	1.399 (2)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.388 (2)	C16—C17	1.3805 (19)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.422 (2)	C17—O4	1.3745 (18)
C6—C14	1.5122 (18)	C17—C18	1.403 (2)
C7—C8	1.511 (2)	C18—O5	1.3685 (17)
C8—N1	1.4617 (19)	C18—C19	1.374 (2)
C8—H8A	0.9700	C19—H19	0.9300
C8—H8B	0.9700	C20—O4	1.420 (2)
C9—N1	1.458 (2)	C20—H20A	0.9600
C9—C10	1.524 (3)	C20—H20B	0.9600
C9—H9A	0.9700	C20—H20C	0.9600
C9—H9B	0.9700	C21—O5	1.419 (2)
C10—C11	1.509 (2)	C21—H21A	0.9600
C10—H10A	0.9700	C21—H21B	0.9600
C10—H10B	0.9700	C21—H21C	0.9600
C11—C19	1.400 (2)	O3—H3	0.8200
C11—C12	1.398 (2)

O1—C1—O2	109.34 (13)	O3—C13—C14	106.08 (11)
O1—C1—H1A	109.8	C12—C13—C14	111.07 (11)
O2—C1—H1A	109.8	O3—C13—H13	109.1
O1—C1—H1B	109.8	C12—C13—H13	109.1
O2—C1—H1B	109.8	C14—C13—H13	109.1
H1A—C1—H1B	108.3	C6—C14—C13	116.11 (11)
C3—C2—C7	124.18 (14)	C6—C14—H14A	108.3
C3—C2—O1	109.97 (13)	C13—C14—H14A	108.3
C7—C2—O1	125.84 (15)	C6—C14—H14B	108.3
C4—C3—C2	121.71 (14)	C13—C14—H14B	108.3
C4—C3—O2	128.23 (15)	H14A—C14—H14B	107.4
C2—C3—O2	110.07 (14)	N1—C15—H15A	109.5
C3—C4—C5	115.72 (14)	N1—C15—H15B	109.5
C3—C4—H4	122.1	H15A—C15—H15B	109.5
C5—C4—H4	122.1	N1—C15—H15C	109.5
C6—C5—C4	123.69 (14)	H15A—C15—H15C	109.5
C6—C5—H5	118.2	H15B—C15—H15C	109.5
C4—C5—H5	118.2	C17—C16—C12	121.96 (14)
C5—C6—C7	119.32 (13)	C17—C16—H16	119.0
C5—C6—C14	119.24 (12)	C12—C16—H16	119.0
C7—C6—C14	121.44 (12)	O4—C17—C16	125.38 (14)
C2—C7—C6	115.33 (13)	O4—C17—C18	115.30 (12)
C2—C7—C8	119.32 (13)	C16—C17—C18	119.31 (14)
C6—C7—C8	125.25 (13)	O5—C18—C19	125.45 (14)
N1—C8—C7	113.84 (12)	O5—C18—C17	115.85 (14)
N1—C8—H8A	108.8	C19—C18—C17	118.70 (13)
C7—C8—H8A	108.8	C18—C19—C11	122.79 (14)
N1—C8—H8B	108.8	C18—C19—H19	118.6
C7—C8—H8B	108.8	C11—C19—H19	118.6
H8A—C8—H8B	107.7	O4—C20—H20A	109.5
N1—C9—C10	112.95 (13)	O4—C20—H20B	109.5
N1—C9—H9A	109.0	H20A—C20—H20B	109.5
C10—C9—H9A	109.0	O4—C20—H20C	109.5
N1—C9—H9B	109.0	H20A—C20—H20C	109.5
C10—C9—H9B	109.0	H20B—C20—H20C	109.5
H9A—C9—H9B	107.8	O5—C21—H21A	109.5
C11—C10—C9	115.88 (14)	O5—C21—H21B	109.5
C11—C10—H10A	108.3	H21A—C21—H21B	109.5
C9—C10—H10A	108.3	O5—C21—H21C	109.5
C11—C10—H10B	108.3	H21A—C21—H21C	109.5
C9—C10—H10B	108.3	H21B—C21—H21C	109.5
H10A—C10—H10B	107.4	C9—N1—C15	112.43 (14)
C19—C11—C12	118.27 (14)	C9—N1—C8	112.27 (13)
C19—C11—C10	117.35 (13)	C15—N1—C8	110.06 (14)
C12—C11—C10	124.35 (13)	C2—O1—C1	105.37 (14)
C16—C12—C11	118.97 (13)	C3—O2—C1	105.22 (13)
C16—C12—C13	118.44 (12)	C13—O3—H3	109.5
C11—C12—C13	122.55 (13)	C17—O4—C20	117.30 (12)
O3—C13—C12	112.35 (11)	C18—O5—C21	116.96 (13)

C7—C2—C3—C4	1.7 (2)	C5—C6—C14—C13	115.88 (14)
O1—C2—C3—C4	−179.25 (14)	C7—C6—C14—C13	−64.86 (17)
C7—C2—C3—O2	−178.17 (14)	O3—C13—C14—C6	−86.03 (14)
O1—C2—C3—O2	0.91 (18)	C12—C13—C14—C6	151.62 (12)
C2—C3—C4—C5	−2.1 (2)	C11—C12—C16—C17	0.2 (2)
O2—C3—C4—C5	177.69 (14)	C13—C12—C16—C17	−177.67 (13)
C3—C4—C5—C6	0.6 (2)	C12—C16—C17—O4	−178.53 (13)
C4—C5—C6—C7	1.4 (2)	C12—C16—C17—C18	0.4 (2)
C4—C5—C6—C14	−179.36 (13)	O4—C17—C18—O5	−0.76 (19)
C3—C2—C7—C6	0.4 (2)	C16—C17—C18—O5	−179.84 (13)
O1—C2—C7—C6	−178.53 (14)	O4—C17—C18—C19	178.58 (13)
C3—C2—C7—C8	176.81 (15)	C16—C17—C18—C19	−0.5 (2)
O1—C2—C7—C8	−2.1 (2)	O5—C18—C19—C11	179.15 (14)
C5—C6—C7—C2	−1.82 (19)	C17—C18—C19—C11	−0.1 (2)
C14—C6—C7—C2	178.92 (13)	C12—C11—C19—C18	0.8 (2)
C5—C6—C7—C8	−177.99 (14)	C10—C11—C19—C18	−177.30 (15)
C14—C6—C7—C8	2.8 (2)	C10—C9—N1—C15	161.30 (15)
C2—C7—C8—N1	139.97 (14)	C10—C9—N1—C8	−73.96 (17)
C6—C7—C8—N1	−44.0 (2)	C7—C8—N1—C9	158.57 (14)
N1—C9—C10—C11	−66.69 (18)	C7—C8—N1—C15	−75.39 (18)
C9—C10—C11—C19	−91.15 (17)	C3—C2—O1—C1	−1.83 (18)
C9—C10—C11—C12	90.89 (19)	C7—C2—O1—C1	177.23 (16)
C19—C11—C12—C16	−0.8 (2)	O2—C1—O1—C2	2.09 (18)
C10—C11—C12—C16	177.11 (14)	C4—C3—O2—C1	−179.40 (16)
C19—C11—C12—C13	176.99 (13)	C2—C3—O2—C1	0.42 (17)
C10—C11—C12—C13	−5.1 (2)	O1—C1—O2—C3	−1.56 (18)
C16—C12—C13—O3	−38.64 (17)	C16—C17—O4—C20	−4.4 (2)
C11—C12—C13—O3	143.52 (14)	C18—C17—O4—C20	176.55 (14)
C16—C12—C13—C14	79.99 (16)	C19—C18—O5—C21	5.0 (2)
C11—C12—C13—C14	−97.85 (15)	C17—C18—O5—C21	−175.74 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.82	2.31	3.0924 (16)	159
C1—H1A···O3ⁱⁱ	0.97	2.41	3.367 (2)	170

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₅NO₅
M_r	371.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.5810 (16), 6.7405 (12), 28.886 (5)
β (°)	92.164 (2)
V (Å³)	1864.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.976, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	13267, 3460, 2721
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.02
No. of reflections	3460
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.18

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), 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
O3—H3···O4ⁱ	0.82	2.31	3.0924 (16)	159
C1—H1A···O3ⁱⁱ	0.97	2.41	3.367 (2)	170

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (NNSF; Nos. 31172365 and 31101469).

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