Dihydro­allocryptopine

Sun, W.; Qin, Y.; Hou, Z.; Yao, Y.; Zhou, L.

doi:10.1107/S1600536811052172

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o69

doi:10.1107/S1600536811052172

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Dihydroallocryptopine

Wenwen Sun,^a Yuyan Qin,^a Zhe Hou,^a Yao Yao ^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 12 November 2011; accepted 3 December 2011; online 10 December 2011)

In the title compound [systematic name: 7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.0^4,9.0^16,20]henicosa-1(21),4,6,8,14,16 (20)-hexaen-2-ol], C₂₁H₂₅NO₅, the benzene rings are inclined at a dihedral angle of 23.16 (5)°. One of the methoxy C atoms is close to coplanar with its attached ring [deviation = 0.129 (3) Å], whereas the other is orientated away from the ring [deviation = −1.124 (2) Å]. The 10-membered ring is highly puckered, and the OH and CH₃ substituents project to the same side of the ring. In the crystal, O—H⋯O hydrogen bonds link the molecules into [010] chains and C—H⋯O and C—H⋯π interactions consolidate the packing.

Related literature

For the synthesis of the title compound, see: Wada et al. (2007 ). For the biological activity of allocryptopine derivatives, see: Morteza et al. (2003 ); Yan et al. (2009 ); Capasso et al. (1997 ); Jeong et al. (2009 ); Zhao et al. (2008 ). For a related structure, see: Valpuesta et al. (2006 ).

Experimental

Crystal data

C₂₁H₂₅NO₅
M_r = 371.42
Monoclinic, P 2₁ /c
a = 14.2557 (19) Å
b = 9.3705 (13) Å
c = 15.278 (2) Å
β = 106.601 (2)°
V = 1955.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.45 × 0.24 × 0.21 mm

Data collection

Bruker SMART APEX II CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.961, T_max = 0.981
14189 measured reflections
3646 independent reflections
2766 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.110
S = 1.02
3646 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5ⁱ	0.82	2.03	2.8380 (16)	168
C7—H7A⋯O4ⁱⁱ	0.97	2.57	3.405 (3)	144
C18—H18⋯O3ⁱⁱⁱ	0.93	2.53	3.229 (2)	132
C7—H7B⋯Cg2^iv	0.97	2.57	3.464 (3)	153
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) -x, -y, -z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536811052172/hb6507sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052172/hb6507Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052172/hb6507Isup3.cml

checkCIF report

Comment top

The allocryptopine derivatives have recently attracted great attention due to their antifungal activity (Morteza et al. 2003), antibacterial activity (Yan et al. 2009), analgesic effect (Capasso et al. 1997), anti-dementia (Jeong et al. 2009; Zhao et al. 2008), and so on. With the interests in the synthesis of allocryptopine derivatives with biological activity, we report here the synthesis and crystal structure of the title compound, (I).

As shown in Fig. 1, 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. In general, the title compound have two oxygenated substituents on the benzene ring and two methoxyl on the other benzene ring. Benzene rings C1/C2/C3/C4/C5/C6 and C10/C11/C16/C17/C18/C19 are inclined with respect to one another with a dihedral angle of 23.16 (5)°.

In the crystal structure, two adjacent molecules are linked by weak intermolecular O—H···O or C—H···O hydrogen bond into a one-dimension chain along b axis. These chains are further connected by C—H···π interaction into two-dimension sheets.

Related literature top

For the synthesis of the title compound, see: Wada et al. (2007). For the biological activity of allocryptopine derivatives, see: Morteza et al. (2003); Yan et al. (2009); Capasso et al. (1997); Jeong et al. (2009); Zhao et al. (2008). For related literature [on what subject?], see: Valpuesta et al. (2006).

Experimental top

The title compound was synthesized according to the literature procedure (Wada et al. 2007), and colourless blocks of (I) were obtained from a solution in methanol by slow evaporation 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. The molecular structure of the title compound (50% displacement ellipsoids).
	Fig. 2. The two-dimension sheet structure of the title compound.

7,8-dimethoxy-11-methyl-17,19-dioxa-11- azatetracyclo[12.7.0.0^4,9.0^16,20]henicosa-1(21),4,6,8,14,16 (20)-hexaen-2-ol top

Crystal data top

C₂₁H₂₅NO₅	F(000) = 792
M_r = 371.42	D_x = 1.261 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.2557 (19) Å	Cell parameters from 3665 reflections
b = 9.3705 (13) Å	θ = 2.6–22.6°
c = 15.278 (2) Å	µ = 0.09 mm⁻¹
β = 106.601 (2)°	T = 296 K
V = 1955.8 (5) Å³	Block, colourless
Z = 4	0.45 × 0.24 × 0.21 mm

Data collection top

Bruker SMART APEX II CCD diffractometer	3646 independent reflections
Radiation source: fine-focus sealed tube	2766 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
phi and ω scans	θ_max = 25.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
T_min = 0.961, T_max = 0.981	k = −11→11
14189 measured reflections	l = −18→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0526P)² + 0.4075P] where P = (F_o² + 2F_c²)/3
3646 reflections	(Δ/σ)_max = 0.001
248 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₁H₂₅NO₅	V = 1955.8 (5) Å³
M_r = 371.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.2557 (19) Å	µ = 0.09 mm⁻¹
b = 9.3705 (13) Å	T = 296 K
c = 15.278 (2) Å	0.45 × 0.24 × 0.21 mm
β = 106.601 (2)°

Data collection top

Bruker SMART APEX II CCD diffractometer	3646 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2766 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.981	R_int = 0.026
14189 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
3646 reflections	Δρ_min = −0.21 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	0.27622 (11)	0.13752 (17)	0.24521 (10)	0.0402 (4)
C2	0.32459 (11)	0.17612 (18)	0.18061 (11)	0.0460 (4)
H2	0.2954	0.1612	0.1186	0.055*
C3	0.41532 (12)	0.2359 (2)	0.21064 (13)	0.0528 (4)
C4	0.46009 (13)	0.2568 (2)	0.30202 (14)	0.0592 (5)
C5	0.41615 (12)	0.2188 (2)	0.36684 (13)	0.0588 (5)
H5	0.4478	0.2329	0.4285	0.071*
C6	0.32187 (11)	0.15767 (19)	0.33900 (11)	0.0464 (4)
C7	0.55723 (15)	0.3447 (3)	0.22467 (16)	0.0776 (6)
H7A	0.6186	0.3106	0.2168	0.093*
H7B	0.5539	0.4471	0.2151	0.093*
C8	0.17251 (11)	0.08232 (16)	0.20842 (9)	0.0375 (3)
H8	0.1545	0.0280	0.2560	0.045*
C9	0.10207 (11)	0.20855 (17)	0.17812 (11)	0.0410 (4)
H9A	0.1234	0.2850	0.2221	0.049*
H9B	0.1079	0.2429	0.1200	0.049*
C10	−0.00464 (11)	0.17974 (16)	0.16778 (10)	0.0381 (3)
C11	−0.04578 (11)	0.20517 (16)	0.23982 (10)	0.0381 (3)
C12	0.01951 (11)	0.25595 (18)	0.33146 (11)	0.0444 (4)
H12A	0.0477	0.3479	0.3243	0.053*
H12B	−0.0189	0.2670	0.3742	0.053*
C13	0.19042 (11)	0.2073 (2)	0.42234 (11)	0.0507 (4)
H13A	0.1902	0.2099	0.4857	0.061*
H13B	0.1988	0.3042	0.4035	0.061*
C14	0.27663 (12)	0.1155 (2)	0.41377 (11)	0.0530 (5)
H14A	0.3274	0.1183	0.4717	0.064*
H14B	0.2544	0.0174	0.4034	0.064*
C15	0.06335 (14)	0.0326 (2)	0.40923 (13)	0.0650 (5)
H15A	0.1137	−0.0388	0.4255	0.098*
H15B	0.0059	−0.0073	0.3672	0.098*
H15C	0.0478	0.0646	0.4631	0.098*
C16	−0.14540 (11)	0.18373 (17)	0.22552 (10)	0.0410 (4)
C17	−0.20575 (11)	0.13956 (18)	0.14017 (11)	0.0452 (4)
C18	−0.16472 (12)	0.11260 (18)	0.07058 (11)	0.0463 (4)
H18	−0.2036	0.0809	0.0142	0.056*
C19	−0.06541 (12)	0.13279 (17)	0.08482 (10)	0.0430 (4)
H19	−0.0385	0.1143	0.0372	0.052*
C20	−0.22408 (15)	0.0958 (2)	0.33403 (14)	0.0674 (5)
H20A	−0.2690	0.0419	0.2868	0.101*
H20B	−0.2569	0.1293	0.3769	0.101*
H20C	−0.1700	0.0361	0.3650	0.101*
C21	−0.36808 (14)	0.0889 (3)	0.04815 (15)	0.0854 (7)
H21A	−0.3646	0.1587	0.0032	0.128*
H21B	−0.4337	0.0846	0.0529	0.128*
H21C	−0.3498	−0.0028	0.0303	0.128*
N1	0.09746 (9)	0.15187 (14)	0.36674 (8)	0.0403 (3)
O1	0.55278 (10)	0.3128 (2)	0.31403 (11)	0.0870 (5)
O2	0.47711 (10)	0.27719 (17)	0.16005 (10)	0.0764 (4)
O3	0.16204 (8)	−0.00602 (12)	0.12969 (7)	0.0458 (3)
H3	0.1735	−0.0892	0.1458	0.069*
O4	−0.30345 (8)	0.12764 (16)	0.13363 (8)	0.0642 (4)
O5	−0.18857 (8)	0.21548 (12)	0.29420 (7)	0.0497 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0378 (8)	0.0418 (9)	0.0418 (9)	0.0010 (7)	0.0127 (7)	−0.0015 (7)
C2	0.0419 (9)	0.0530 (10)	0.0431 (9)	0.0002 (7)	0.0121 (7)	0.0017 (7)
C3	0.0446 (10)	0.0587 (11)	0.0594 (11)	−0.0037 (8)	0.0216 (8)	0.0003 (9)
C4	0.0407 (9)	0.0668 (12)	0.0694 (12)	−0.0113 (9)	0.0147 (9)	−0.0111 (10)
C5	0.0432 (10)	0.0793 (14)	0.0511 (10)	−0.0077 (9)	0.0089 (8)	−0.0145 (9)
C6	0.0395 (9)	0.0553 (10)	0.0428 (9)	0.0013 (7)	0.0091 (7)	−0.0051 (8)
C7	0.0530 (12)	0.0853 (16)	0.0995 (17)	−0.0185 (11)	0.0298 (12)	−0.0081 (13)
C8	0.0417 (8)	0.0422 (9)	0.0301 (7)	−0.0026 (7)	0.0125 (6)	−0.0025 (6)
C9	0.0429 (9)	0.0425 (9)	0.0389 (8)	−0.0011 (7)	0.0140 (7)	0.0029 (7)
C10	0.0408 (8)	0.0357 (8)	0.0375 (8)	0.0027 (6)	0.0111 (6)	0.0027 (6)
C11	0.0407 (8)	0.0346 (8)	0.0381 (8)	0.0007 (6)	0.0095 (7)	−0.0015 (6)
C12	0.0430 (9)	0.0473 (9)	0.0436 (9)	−0.0029 (7)	0.0136 (7)	−0.0117 (7)
C13	0.0456 (9)	0.0690 (12)	0.0369 (8)	−0.0084 (8)	0.0108 (7)	−0.0137 (8)
C14	0.0440 (9)	0.0768 (13)	0.0347 (8)	−0.0011 (9)	0.0057 (7)	−0.0011 (8)
C15	0.0613 (11)	0.0714 (13)	0.0612 (12)	−0.0116 (10)	0.0156 (9)	0.0148 (10)
C16	0.0408 (8)	0.0424 (9)	0.0413 (9)	0.0025 (7)	0.0142 (7)	−0.0021 (7)
C17	0.0376 (9)	0.0493 (10)	0.0456 (9)	0.0016 (7)	0.0069 (7)	−0.0019 (7)
C18	0.0458 (9)	0.0531 (10)	0.0350 (8)	0.0012 (8)	0.0036 (7)	−0.0040 (7)
C19	0.0478 (9)	0.0462 (9)	0.0357 (8)	0.0048 (7)	0.0130 (7)	0.0005 (7)
C20	0.0694 (13)	0.0749 (14)	0.0672 (12)	−0.0005 (11)	0.0347 (10)	0.0095 (10)
C21	0.0436 (11)	0.128 (2)	0.0719 (14)	−0.0027 (12)	−0.0039 (10)	−0.0165 (14)
N1	0.0398 (7)	0.0478 (8)	0.0326 (6)	−0.0057 (6)	0.0095 (5)	−0.0040 (6)
O1	0.0522 (8)	0.1244 (14)	0.0852 (11)	−0.0369 (9)	0.0208 (7)	−0.0178 (10)
O2	0.0563 (8)	0.1040 (12)	0.0760 (9)	−0.0229 (8)	0.0303 (7)	0.0018 (8)
O3	0.0541 (7)	0.0482 (7)	0.0363 (6)	−0.0031 (6)	0.0150 (5)	−0.0074 (5)
O4	0.0363 (6)	0.0958 (10)	0.0561 (7)	−0.0040 (6)	0.0062 (5)	−0.0098 (7)
O5	0.0496 (7)	0.0551 (7)	0.0499 (7)	−0.0007 (5)	0.0229 (5)	−0.0060 (5)

Geometric parameters (Å, º) top

C1—C2	1.403 (2)	C12—H12B	0.9700
C1—C6	1.407 (2)	C13—N1	1.4506 (19)
C1—C8	1.515 (2)	C13—C14	1.536 (2)
C2—C3	1.363 (2)	C13—H13A	0.9700
C2—H2	0.9300	C13—H13B	0.9700
C3—C4	1.373 (3)	C14—H14A	0.9700
C3—O2	1.383 (2)	C14—H14B	0.9700
C4—C5	1.362 (3)	C15—N1	1.445 (2)
C4—O1	1.384 (2)	C15—H15A	0.9600
C5—C6	1.410 (2)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—C14	1.516 (2)	C16—O5	1.3920 (18)
C7—O1	1.417 (3)	C16—C17	1.404 (2)
C7—O2	1.427 (2)	C17—O4	1.3720 (19)
C7—H7A	0.9700	C17—C18	1.375 (2)
C7—H7B	0.9700	C18—C19	1.383 (2)
C8—O3	1.4323 (17)	C18—H18	0.9300
C8—C9	1.535 (2)	C19—H19	0.9300
C8—H8	0.9800	C20—O5	1.435 (2)
C9—C10	1.508 (2)	C20—H20A	0.9600
C9—H9A	0.9700	C20—H20B	0.9600
C9—H9B	0.9700	C20—H20C	0.9600
C10—C19	1.387 (2)	C21—O4	1.414 (2)
C10—C11	1.407 (2)	C21—H21A	0.9600
C11—C16	1.388 (2)	C21—H21B	0.9600
C11—C12	1.519 (2)	C21—H21C	0.9600
C12—N1	1.461 (2)	O3—H3	0.8200
C12—H12A	0.9700

C2—C1—C6	120.30 (14)	N1—C13—H13A	109.3
C2—C1—C8	116.79 (13)	C14—C13—H13A	109.3
C6—C1—C8	122.82 (13)	N1—C13—H13B	109.3
C3—C2—C1	118.61 (15)	C14—C13—H13B	109.3
C3—C2—H2	120.7	H13A—C13—H13B	108.0
C1—C2—H2	120.7	C6—C14—C13	116.17 (15)
C2—C3—C4	121.44 (16)	C6—C14—H14A	108.2
C2—C3—O2	128.43 (17)	C13—C14—H14A	108.2
C4—C3—O2	110.06 (15)	C6—C14—H14B	108.2
C5—C4—C3	121.68 (16)	C13—C14—H14B	108.2
C5—C4—O1	128.52 (18)	H14A—C14—H14B	107.4
C3—C4—O1	109.74 (17)	N1—C15—H15A	109.5
C4—C5—C6	118.93 (16)	N1—C15—H15B	109.5
C4—C5—H5	120.5	H15A—C15—H15B	109.5
C6—C5—H5	120.5	N1—C15—H15C	109.5
C1—C6—C5	119.03 (15)	H15A—C15—H15C	109.5
C1—C6—C14	124.04 (14)	H15B—C15—H15C	109.5
C5—C6—C14	116.92 (14)	C11—C16—O5	120.21 (13)
O1—C7—O2	109.03 (15)	C11—C16—C17	121.11 (14)
O1—C7—H7A	109.9	O5—C16—C17	118.53 (13)
O2—C7—H7A	109.9	O4—C17—C18	125.15 (14)
O1—C7—H7B	109.9	O4—C17—C16	115.57 (14)
O2—C7—H7B	109.9	C18—C17—C16	119.28 (14)
H7A—C7—H7B	108.3	C17—C18—C19	119.72 (14)
O3—C8—C1	111.43 (12)	C17—C18—H18	120.1
O3—C8—C9	106.85 (12)	C19—C18—H18	120.1
C1—C8—C9	109.50 (13)	C18—C19—C10	122.10 (14)
O3—C8—H8	109.7	C18—C19—H19	118.9
C1—C8—H8	109.7	C10—C19—H19	118.9
C9—C8—H8	109.7	O5—C20—H20A	109.5
C10—C9—C8	116.55 (13)	O5—C20—H20B	109.5
C10—C9—H9A	108.2	H20A—C20—H20B	109.5
C8—C9—H9A	108.2	O5—C20—H20C	109.5
C10—C9—H9B	108.2	H20A—C20—H20C	109.5
C8—C9—H9B	108.2	H20B—C20—H20C	109.5
H9A—C9—H9B	107.3	O4—C21—H21A	109.5
C19—C10—C11	118.51 (14)	O4—C21—H21B	109.5
C19—C10—C9	120.04 (13)	H21A—C21—H21B	109.5
C11—C10—C9	121.40 (13)	O4—C21—H21C	109.5
C16—C11—C10	119.24 (13)	H21A—C21—H21C	109.5
C16—C11—C12	121.34 (13)	H21B—C21—H21C	109.5
C10—C11—C12	119.42 (13)	C15—N1—C13	112.48 (14)
N1—C12—C11	109.40 (12)	C15—N1—C12	111.35 (14)
N1—C12—H12A	109.8	C13—N1—C12	116.64 (13)
C11—C12—H12A	109.8	C4—O1—C7	104.83 (15)
N1—C12—H12B	109.8	C3—O2—C7	104.43 (15)
C11—C12—H12B	109.8	C8—O3—H3	109.5
H12A—C12—H12B	108.2	C17—O4—C21	117.92 (14)
N1—C13—C14	111.64 (14)	C16—O5—C20	115.97 (13)

C6—C1—C2—C3	−1.3 (2)	C1—C6—C14—C13	−71.7 (2)
C8—C1—C2—C3	175.33 (15)	C5—C6—C14—C13	109.25 (18)
C1—C2—C3—C4	0.9 (3)	N1—C13—C14—C6	90.26 (18)
C1—C2—C3—O2	177.59 (17)	C10—C11—C16—O5	−176.56 (13)
C2—C3—C4—C5	0.1 (3)	C12—C11—C16—O5	3.2 (2)
O2—C3—C4—C5	−177.16 (18)	C10—C11—C16—C17	−1.1 (2)
C2—C3—C4—O1	177.33 (17)	C12—C11—C16—C17	178.70 (15)
O2—C3—C4—O1	0.1 (2)	C11—C16—C17—O4	−177.48 (14)
C3—C4—C5—C6	−0.6 (3)	O5—C16—C17—O4	−1.9 (2)
O1—C4—C5—C6	−177.3 (2)	C11—C16—C17—C18	2.2 (2)
C2—C1—C6—C5	0.8 (3)	O5—C16—C17—C18	177.73 (14)
C8—C1—C6—C5	−175.64 (15)	O4—C17—C18—C19	177.98 (16)
C2—C1—C6—C14	−178.21 (16)	C16—C17—C18—C19	−1.7 (2)
C8—C1—C6—C14	5.3 (3)	C17—C18—C19—C10	0.1 (3)
C4—C5—C6—C1	0.2 (3)	C11—C10—C19—C18	1.0 (2)
C4—C5—C6—C14	179.25 (17)	C9—C10—C19—C18	−176.33 (15)
C2—C1—C8—O3	38.31 (19)	C14—C13—N1—C15	79.54 (18)
C6—C1—C8—O3	−145.11 (15)	C14—C13—N1—C12	−150.04 (14)
C2—C1—C8—C9	−79.68 (17)	C11—C12—N1—C15	−80.48 (17)
C6—C1—C8—C9	96.90 (17)	C11—C12—N1—C13	148.58 (13)
O3—C8—C9—C10	77.80 (16)	C5—C4—O1—C7	−174.7 (2)
C1—C8—C9—C10	−161.39 (13)	C3—C4—O1—C7	8.3 (2)
C8—C9—C10—C19	−89.37 (18)	O2—C7—O1—C4	−13.5 (2)
C8—C9—C10—C11	93.35 (17)	C2—C3—O2—C7	174.7 (2)
C19—C10—C11—C16	−0.5 (2)	C4—C3—O2—C7	−8.3 (2)
C9—C10—C11—C16	176.82 (14)	O1—C7—O2—C3	13.6 (2)
C19—C10—C11—C12	179.70 (14)	C18—C17—O4—C21	−2.1 (3)
C9—C10—C11—C12	−3.0 (2)	C16—C17—O4—C21	177.58 (18)
C16—C11—C12—N1	121.81 (15)	C11—C16—O5—C20	−112.30 (17)
C10—C11—C12—N1	−58.39 (19)	C17—C16—O5—C20	72.12 (19)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5ⁱ	0.82	2.03	2.8380 (16)	168
C7—H7A···O4ⁱⁱ	0.97	2.57	3.405 (3)	144
C18—H18···O3ⁱⁱⁱ	0.93	2.53	3.229 (2)	132
C7—H7B···Cg2^iv	0.97	2.57	3.464 (3)	153

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −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)	14.2557 (19), 9.3705 (13), 15.278 (2)
β (°)	106.601 (2)
V (Å³)	1955.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.45 × 0.24 × 0.21

Data collection
Diffractometer	Bruker SMART APEX II CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.961, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	14189, 3646, 2766
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.110, 1.02
No. of reflections	3646
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5ⁱ	0.82	2.03	2.8380 (16)	168
C7—H7A···O4ⁱⁱ	0.97	2.57	3.405 (3)	144
C18—H18···O3ⁱⁱⁱ	0.93	2.53	3.229 (2)	132
C7—H7B···Cg2^iv	0.97	2.57	3.464 (3)	153

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (NNSF; No. 31172365; 31101469).

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