(9S,13R,14S)-7,8-Didehydro-4-(4-iodo­benz­yloxy)-3,7-dimeth­oxy-17-methyl­morphinan-6-one monohydrate

Zheng, X.-L.; Jiang, N.-F.

doi:10.1107/S1600536810040286

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2817

https://doi.org/10.1107/S1600536810040286

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(9S,13R,14S)-7,8-Didehydro-4-(4-iodobenzyloxy)-3,7-dimethoxy-17-methylmorphinan-6-one monohydrate

Xing-Liang Zheng ^a ^* and Ning-Fei Jiang ^a

^aSchool of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, People's Republic of China
^*Correspondence e-mail: xingliangzheng@163.com

(Received 17 August 2010; accepted 8 October 2010; online 20 October 2010)

In the title compound, C₂₆H₂₈INO₄·H₂O, benzene rings are inclined at a dihedral angle of 69.9 (1)°. The N-containing ring exhibits a chair conformation, while the other rings approximate to envelope conformations. In the crystal, the uncoordinated water molecule forms intermolecular O—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For the biological activity of sinomenine derivatives and other related compounds, see: Liu et al. (1994 , 1996 , 1997 ); Mark et al. (2003 ); Ye et al. (2004 ). For the synthesis of the title compound, see: Mitsunobu (1981 ). For related structures, see: Li et al. (2009 ); Batterham et al. (1965 ).

Experimental

Crystal data

C₂₆H₂₈INO₄·H₂O
M_r = 563.41
Monoclinic, P 2₁
a = 8.9005 (8) Å
b = 14.9221 (14) Å
c = 9.2426 (9) Å
β = 91.432 (2)°
V = 1227.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.34 mm⁻¹
T = 293 K
0.31 × 0.30 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.482, T_max = 1.000
7231 measured reflections
5047 independent reflections
4844 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.087
S = 1.07
5047 reflections
309 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.49 e Å⁻³
Absolute structure: Flack (1983 ), 2311 Friedel pairs
Flack parameter: −0.016 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5C⋯O3ⁱ	0.84 (3)	2.13 (3)	2.946 (5)	164 (6)
O5—H5D⋯N1ⁱⁱ	0.84 (3)	2.26 (11)	2.924 (6)	135 (13)
Symmetry codes: (i) x, y, z+1; (ii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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: https://doi.org/10.1107/S1600536810040286/bh2309sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040286/bh2309Isup2.hkl

checkCIF report

Comment top

We synthesized a new sinomenine derivative (9S,13R,14S)-7,8-didehydro-4-(4'-iodiobenzyloxy)-3,7-dimethoxy-17-methyl-morphinan-6-one monohydrate. Herein, its crystal structure is reported. Biological effects of sinomenine derivatives and related compounds have been described (Liu et al., 1994, 1996, 1997; Mark et al., 2003; Ye et al., 2004).

The molecular structure of (I) is shown in Fig. 1. The crystal structure is stabilized by O—H···O and O—H···N hydrogen bonds linking sinomenine derivative and the water molecule, and weak C—H···O hydrogen bonds between molecules (Fig. 2). Significant aromatic stacking interactions were not found. There exist two planes in the molecule of the title compound: atoms C1/C2/C3/C4/C12/C11 form the benzene plane (I), and atoms C19···C24 form the benzene plane substituted by Iodine (II). The angle between the two planes is 69.9 (1)°. Rings C [C5/C6/C7/C8/C14/C13] and B [C9···C14] in the molecule approximate both an envelope conformation. In contrast, ring D [C9/N1/C16/C15/C13/C14] exhibits an almost regular chair conformation. Similar features have been described in related compounds (Li et al., 2009; Batterham et al., 1965).

Related literature top

For the biological activity of sinomenine derivatives and other related compounds, see: Liu et al. (1994, 1996, 1997); Mark et al. (2003); Ye et al. (2004). For the synthesis of the title compound, see: Mitsunobu (1981). For related structures, see: Li et al. (2009); Batterham et al. (1965).

Experimental top

The title compound was obtained according to the method of Mitsunobu (1981). Light yellow blocks of (I) were grown from a dichloromethane solution.

Structure description top

For the biological activity of sinomenine derivatives and other related compounds, see: Liu et al. (1994, 1996, 1997); Mark et al. (2003); Ye et al. (2004). For the synthesis of the title compound, see: Mitsunobu (1981). For related structures, see: Li et al. (2009); Batterham et al. (1965).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (I) showing 50% probability displacement ellipsoids.
	Fig. 2. Packing structure of the title compound.

(9S,13R,14S)-7,8-Didehydro-4-(4-iodobenzyloxy)-3,7- dimethoxy-17-methylmorphinan-6-one monohydrate top

Crystal data top

C₂₆H₂₈INO₄·H₂O	F(000) = 572
M_r = 563.41	D_x = 1.525 Mg m⁻³
Monoclinic, P2₁	Melting point: 412 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 8.9005 (8) Å	Cell parameters from 4522 reflections
b = 14.9221 (14) Å	θ = 4.6–56.4°
c = 9.2426 (9) Å	µ = 1.34 mm⁻¹
β = 91.432 (2)°	T = 293 K
V = 1227.2 (2) Å³	Prismatic, colourless
Z = 2	0.31 × 0.30 × 0.23 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5047 independent reflections
Radiation source: fine-focus sealed tube	4844 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000	h = −6→11
T_min = 0.482, T_max = 1.000	k = −18→19
7231 measured reflections	l = −11→11

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0485P)² + 0.0909P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.004
5047 reflections	Δρ_max = 0.98 e Å⁻³
309 parameters	Δρ_min = −0.49 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 2311 Friedel pairs
0 constraints	Absolute structure parameter: −0.016 (17)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₆H₂₈INO₄·H₂O	V = 1227.2 (2) Å³
M_r = 563.41	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.9005 (8) Å	µ = 1.34 mm⁻¹
b = 14.9221 (14) Å	T = 293 K
c = 9.2426 (9) Å	0.31 × 0.30 × 0.23 mm
β = 91.432 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5047 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000	4844 reflections with I > 2σ(I)
T_min = 0.482, T_max = 1.000	R_int = 0.038
7231 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.087	Δρ_max = 0.98 e Å⁻³
S = 1.07	Δρ_min = −0.49 e Å⁻³
5047 reflections	Absolute structure: Flack (1983), 2311 Friedel pairs
309 parameters	Absolute structure parameter: −0.016 (17)
4 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	1.01684 (3)	1.24508 (2)	0.40697 (3)	0.05793 (10)
N1	0.7186 (4)	0.5021 (2)	0.1708 (4)	0.0481 (8)
O1	0.3354 (3)	0.90402 (19)	0.2691 (3)	0.0528 (7)
O2	0.6158 (3)	0.86212 (17)	0.2123 (2)	0.0381 (5)
O3	0.7304 (3)	0.86778 (19)	−0.1786 (3)	0.0532 (7)
O4	0.5676 (3)	0.7548 (3)	−0.3349 (3)	0.0504 (7)
O5	0.9701 (6)	0.9909 (3)	0.9213 (6)	0.0898 (14)
C1	0.2856 (4)	0.6717 (3)	0.1460 (5)	0.0474 (9)
H1	0.2104	0.6290	0.1330	0.057*
C2	0.2469 (4)	0.7561 (4)	0.1937 (4)	0.0497 (10)
H2	0.1469	0.7705	0.2092	0.060*
C3	0.3580 (4)	0.8183 (3)	0.2179 (4)	0.0412 (8)
C4	0.5086 (4)	0.7971 (2)	0.1890 (4)	0.0342 (7)
C5	0.7896 (4)	0.7650 (2)	0.0106 (4)	0.0386 (8)
H5A	0.7968	0.8164	0.0745	0.046*
H5B	0.8910	0.7451	−0.0082	0.046*
C6	0.7159 (4)	0.7938 (2)	−0.1298 (4)	0.0392 (8)
C7	0.6302 (4)	0.7238 (2)	−0.2098 (4)	0.0381 (8)
C8	0.6280 (4)	0.6389 (2)	−0.1618 (4)	0.0407 (8)
H8	0.5790	0.5955	−0.2178	0.049*
C9	0.6273 (4)	0.5306 (2)	0.0456 (4)	0.0422 (8)
H10	0.6290	0.4820	−0.0256	0.051*
C10	0.4626 (4)	0.5535 (3)	0.0708 (4)	0.0471 (9)
H11A	0.4055	0.5417	−0.0179	0.056*
H11B	0.4254	0.5133	0.1443	0.056*
C11	0.4318 (4)	0.6484 (3)	0.1170 (4)	0.0382 (7)
C12	0.5457 (4)	0.7138 (2)	0.1318 (4)	0.0314 (7)
C13	0.7065 (4)	0.6896 (2)	0.0881 (4)	0.0348 (7)
C14	0.7012 (4)	0.6117 (2)	−0.0221 (4)	0.0364 (7)
H9	0.8053	0.5952	−0.0422	0.044*
C15	0.7966 (4)	0.6576 (3)	0.2203 (4)	0.0442 (8)
H15A	0.8999	0.6473	0.1937	0.053*
H15B	0.7967	0.7041	0.2938	0.053*
C16	0.7328 (5)	0.5722 (3)	0.2826 (4)	0.0494 (9)
H16A	0.7982	0.5511	0.3610	0.059*
H16B	0.6349	0.5844	0.3218	0.059*
C17	0.6656 (6)	0.4173 (4)	0.2330 (6)	0.0710 (14)
H17A	0.5684	0.4262	0.2734	0.107*
H17B	0.7352	0.3979	0.3077	0.107*
H17C	0.6588	0.3725	0.1586	0.107*
C18	0.6493 (5)	0.8804 (3)	0.3618 (4)	0.0435 (8)
H18A	0.7019	0.8299	0.4057	0.052*
H18B	0.5571	0.8900	0.4132	0.052*
C19	0.7461 (4)	0.9628 (2)	0.3707 (4)	0.0369 (7)
C20	0.7795 (5)	0.9999 (3)	0.5060 (4)	0.0464 (9)
H20	0.7478	0.9713	0.5892	0.056*
C21	0.8598 (5)	1.0793 (3)	0.5171 (4)	0.0479 (9)
H21	0.8808	1.1045	0.6074	0.057*
C22	0.9082 (4)	1.1204 (3)	0.3940 (4)	0.0410 (8)
C23	0.8819 (4)	1.0833 (3)	0.2597 (4)	0.0443 (9)
H23	0.9172	1.1110	0.1771	0.053*
C24	0.8021 (4)	1.0042 (3)	0.2494 (4)	0.0398 (8)
H24	0.7855	0.9781	0.1590	0.048*
C25	0.4769 (6)	0.6931 (5)	−0.4172 (5)	0.0738 (16)
H25A	0.5393	0.6463	−0.4539	0.111*
H25B	0.4285	0.7241	−0.4966	0.111*
H25C	0.4022	0.6677	−0.3564	0.111*
C26	0.1839 (6)	0.9304 (4)	0.2891 (7)	0.0756 (16)
H26A	0.1239	0.9135	0.2058	0.113*
H26B	0.1794	0.9942	0.3016	0.113*
H26C	0.1461	0.9014	0.3735	0.113*
H5C	0.913 (6)	0.954 (4)	0.879 (7)	0.10 (2)*
H5D	1.060 (5)	0.976 (7)	0.937 (14)	0.11 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.05580 (15)	0.06209 (16)	0.05586 (15)	−0.02060 (14)	0.00072 (10)	−0.00469 (15)
N1	0.0504 (19)	0.0413 (17)	0.0528 (19)	0.0021 (14)	0.0037 (15)	0.0087 (14)
O1	0.0508 (16)	0.0474 (16)	0.0610 (17)	0.0130 (12)	0.0148 (13)	0.0009 (13)
O2	0.0438 (14)	0.0384 (13)	0.0321 (11)	−0.0044 (10)	0.0006 (10)	−0.0043 (10)
O3	0.0535 (17)	0.0367 (15)	0.0698 (18)	−0.0028 (12)	0.0062 (14)	0.0022 (13)
O4	0.0530 (14)	0.0547 (19)	0.0433 (12)	−0.0036 (16)	−0.0010 (10)	0.0055 (15)
O5	0.072 (3)	0.088 (3)	0.111 (3)	−0.028 (2)	0.029 (2)	−0.041 (3)
C1	0.0345 (18)	0.057 (3)	0.051 (2)	−0.0086 (17)	0.0049 (17)	0.0091 (18)
C2	0.0323 (15)	0.061 (3)	0.056 (2)	0.0032 (19)	0.0095 (14)	0.003 (2)
C3	0.0401 (19)	0.047 (2)	0.0368 (18)	0.0065 (16)	0.0071 (15)	0.0082 (15)
C4	0.0339 (18)	0.0390 (19)	0.0299 (17)	−0.0021 (14)	0.0027 (14)	0.0023 (14)
C5	0.0313 (15)	0.039 (2)	0.0459 (17)	−0.0061 (13)	0.0084 (13)	−0.0071 (13)
C6	0.0322 (17)	0.0351 (19)	0.051 (2)	−0.0019 (14)	0.0151 (15)	−0.0063 (15)
C7	0.0383 (16)	0.042 (2)	0.0345 (16)	−0.0025 (13)	0.0064 (13)	−0.0022 (13)
C8	0.046 (2)	0.0396 (19)	0.0372 (18)	−0.0082 (16)	0.0044 (15)	−0.0095 (15)
C9	0.049 (2)	0.039 (2)	0.0388 (18)	−0.0050 (16)	0.0037 (16)	−0.0026 (14)
C10	0.049 (2)	0.042 (2)	0.050 (2)	−0.0103 (16)	−0.0032 (17)	0.0006 (16)
C11	0.0362 (17)	0.0435 (19)	0.0349 (17)	−0.0070 (15)	−0.0007 (13)	0.0034 (14)
C12	0.0296 (16)	0.0366 (18)	0.0279 (16)	−0.0020 (12)	−0.0014 (13)	0.0027 (12)
C13	0.0327 (16)	0.0387 (18)	0.0330 (16)	−0.0015 (13)	0.0019 (13)	−0.0044 (14)
C14	0.0392 (19)	0.0327 (18)	0.0376 (17)	−0.0018 (14)	0.0065 (14)	−0.0045 (13)
C15	0.0372 (18)	0.052 (2)	0.044 (2)	0.0054 (16)	−0.0039 (15)	−0.0057 (16)
C16	0.047 (2)	0.059 (3)	0.042 (2)	0.0088 (18)	−0.0034 (17)	0.0075 (18)
C17	0.080 (4)	0.054 (3)	0.079 (3)	−0.002 (2)	0.002 (3)	0.024 (2)
C18	0.054 (2)	0.040 (2)	0.0365 (18)	0.0025 (17)	−0.0015 (16)	0.0011 (14)
C19	0.0350 (17)	0.0387 (18)	0.0369 (18)	0.0058 (14)	−0.0029 (14)	0.0005 (14)
C20	0.055 (2)	0.051 (2)	0.0335 (18)	−0.0047 (18)	0.0038 (16)	0.0015 (16)
C21	0.050 (2)	0.064 (3)	0.0301 (17)	−0.0084 (18)	0.0003 (15)	−0.0069 (16)
C22	0.0321 (17)	0.048 (2)	0.0431 (19)	−0.0019 (15)	0.0014 (14)	−0.0044 (15)
C23	0.0392 (19)	0.060 (2)	0.0335 (18)	−0.0021 (17)	0.0041 (14)	0.0028 (16)
C24	0.0414 (19)	0.049 (2)	0.0295 (16)	0.0028 (16)	−0.0013 (14)	−0.0054 (14)
C25	0.084 (4)	0.092 (4)	0.044 (3)	−0.024 (3)	−0.017 (3)	0.009 (2)
C26	0.063 (3)	0.065 (3)	0.100 (4)	0.023 (2)	0.036 (3)	0.007 (3)

Geometric parameters (Å, º) top

I1—C22	2.099 (4)	C10—H11B	0.9700
N1—C9	1.461 (5)	C11—C12	1.411 (5)
N1—C17	1.472 (6)	C12—C13	1.541 (5)
N1—C16	1.474 (6)	C13—C15	1.521 (5)
O1—C3	1.380 (5)	C13—C14	1.546 (4)
O1—C26	1.421 (5)	C14—H9	0.9800
O2—C4	1.374 (4)	C15—C16	1.516 (6)
O2—C18	1.432 (4)	C15—H15A	0.9700
O3—C6	1.201 (5)	C15—H15B	0.9700
O4—C7	1.353 (4)	C16—H16A	0.9700
O4—C25	1.430 (6)	C16—H16B	0.9700
O5—H5C	0.84 (3)	C17—H17A	0.9600
O5—H5D	0.84 (3)	C17—H17B	0.9600
C1—C11	1.380 (5)	C17—H17C	0.9600
C1—C2	1.381 (7)	C18—C19	1.502 (5)
C1—H1	0.9300	C18—H18A	0.9700
C2—C3	1.370 (6)	C18—H18B	0.9700
C2—H2	0.9300	C19—C24	1.384 (5)
C3—C4	1.410 (5)	C19—C20	1.393 (5)
C4—C12	1.392 (5)	C20—C21	1.387 (6)
C5—C6	1.501 (5)	C20—H20	0.9300
C5—C13	1.534 (5)	C21—C22	1.371 (5)
C5—H5A	0.9700	C21—H21	0.9300
C5—H5B	0.9700	C22—C23	1.375 (5)
C6—C7	1.480 (5)	C23—C24	1.379 (6)
C7—C8	1.343 (5)	C23—H23	0.9300
C8—C14	1.488 (5)	C24—H24	0.9300
C8—H8	0.9300	C25—H25A	0.9600
C9—C14	1.520 (5)	C25—H25B	0.9600
C9—C10	1.528 (5)	C25—H25C	0.9600
C9—H10	0.9800	C26—H26A	0.9600
C10—C11	1.507 (6)	C26—H26B	0.9600
C10—H11A	0.9700	C26—H26C	0.9600

C9—N1—C17	112.5 (4)	C8—C14—C13	111.8 (3)
C9—N1—C16	112.6 (3)	C9—C14—C13	109.5 (3)
C17—N1—C16	111.0 (4)	C8—C14—H9	107.4
C3—O1—C26	116.6 (4)	C9—C14—H9	107.4
C4—O2—C18	114.4 (3)	C13—C14—H9	107.4
C7—O4—C25	116.7 (4)	C16—C15—C13	111.9 (3)
H5C—O5—H5D	118 (5)	C16—C15—H15A	109.2
C11—C1—C2	122.4 (4)	C13—C15—H15A	109.2
C11—C1—H1	118.8	C16—C15—H15B	109.2
C2—C1—H1	118.8	C13—C15—H15B	109.2
C3—C2—C1	119.0 (3)	H15A—C15—H15B	107.9
C3—C2—H2	120.5	N1—C16—C15	110.9 (3)
C1—C2—H2	120.5	N1—C16—H16A	109.4
C2—C3—O1	124.9 (4)	C15—C16—H16A	109.4
C2—C3—C4	120.2 (4)	N1—C16—H16B	109.4
O1—C3—C4	114.9 (4)	C15—C16—H16B	109.4
O2—C4—C12	121.3 (3)	H16A—C16—H16B	108.0
O2—C4—C3	118.1 (3)	N1—C17—H17A	109.5
C12—C4—C3	120.5 (4)	N1—C17—H17B	109.5
C6—C5—C13	114.1 (3)	H17A—C17—H17B	109.5
C6—C5—H5A	108.7	N1—C17—H17C	109.5
C13—C5—H5A	108.7	H17A—C17—H17C	109.5
C6—C5—H5B	108.7	H17B—C17—H17C	109.5
C13—C5—H5B	108.7	O2—C18—C19	108.3 (3)
H5A—C5—H5B	107.6	O2—C18—H18A	110.0
O3—C6—C7	121.3 (4)	C19—C18—H18A	110.0
O3—C6—C5	122.6 (3)	O2—C18—H18B	110.0
C7—C6—C5	116.0 (3)	C19—C18—H18B	110.0
C8—C7—O4	126.6 (3)	H18A—C18—H18B	108.4
C8—C7—C6	120.8 (3)	C24—C19—C20	118.5 (4)
O4—C7—C6	112.5 (3)	C24—C19—C18	122.6 (3)
C7—C8—C14	122.3 (3)	C20—C19—C18	119.0 (3)
C7—C8—H8	118.8	C21—C20—C19	120.3 (4)
C14—C8—H8	118.8	C21—C20—H20	119.8
N1—C9—C14	108.7 (3)	C19—C20—H20	119.8
N1—C9—C10	117.5 (3)	C22—C21—C20	119.5 (4)
C14—C9—C10	108.2 (3)	C22—C21—H21	120.2
N1—C9—H10	107.4	C20—C21—H21	120.2
C14—C9—H10	107.4	C21—C22—C23	121.3 (4)
C10—C9—H10	107.4	C21—C22—I1	120.2 (3)
C11—C10—C9	115.8 (3)	C23—C22—I1	118.5 (3)
C11—C10—H11A	108.3	C22—C23—C24	118.9 (3)
C9—C10—H11A	108.3	C22—C23—H23	120.6
C11—C10—H11B	108.3	C24—C23—H23	120.6
C9—C10—H11B	108.3	C23—C24—C19	121.5 (3)
H11A—C10—H11B	107.4	C23—C24—H24	119.3
C1—C11—C12	119.0 (4)	C19—C24—H24	119.3
C1—C11—C10	118.1 (3)	O4—C25—H25A	109.5
C12—C11—C10	122.9 (3)	O4—C25—H25B	109.5
C4—C12—C11	118.5 (3)	H25A—C25—H25B	109.5
C4—C12—C13	122.6 (3)	O4—C25—H25C	109.5
C11—C12—C13	118.8 (3)	H25A—C25—H25C	109.5
C15—C13—C5	110.8 (3)	H25B—C25—H25C	109.5
C15—C13—C12	109.7 (3)	O1—C26—H26A	109.5
C5—C13—C12	114.3 (3)	O1—C26—H26B	109.5
C15—C13—C14	107.5 (3)	H26A—C26—H26B	109.5
C5—C13—C14	104.5 (3)	O1—C26—H26C	109.5
C12—C13—C14	109.6 (3)	H26A—C26—H26C	109.5
C8—C14—C9	112.9 (3)	H26B—C26—H26C	109.5

C11—C1—C2—C3	−2.2 (6)	C6—C5—C13—C12	−61.4 (4)
C1—C2—C3—O1	−178.2 (3)	C6—C5—C13—C14	58.5 (4)
C1—C2—C3—C4	2.4 (6)	C4—C12—C13—C15	84.0 (4)
C26—O1—C3—C2	−4.1 (6)	C11—C12—C13—C15	−94.3 (4)
C26—O1—C3—C4	175.4 (4)	C4—C12—C13—C5	−41.1 (4)
C18—O2—C4—C12	−110.7 (3)	C11—C12—C13—C5	140.6 (3)
C18—O2—C4—C3	72.3 (4)	C4—C12—C13—C14	−158.1 (3)
C2—C3—C4—O2	178.8 (3)	C11—C12—C13—C14	23.6 (4)
O1—C3—C4—O2	−0.7 (5)	C7—C8—C14—C9	152.3 (3)
C2—C3—C4—C12	1.9 (5)	C7—C8—C14—C13	28.2 (5)
O1—C3—C4—C12	−177.6 (3)	N1—C9—C14—C8	172.5 (3)
C13—C5—C6—O3	153.4 (3)	C10—C9—C14—C8	−59.0 (4)
C13—C5—C6—C7	−29.9 (4)	N1—C9—C14—C13	−62.2 (4)
C25—O4—C7—C8	6.9 (6)	C10—C9—C14—C13	66.4 (4)
C25—O4—C7—C6	−177.4 (4)	C15—C13—C14—C8	−174.5 (3)
O3—C6—C7—C8	172.9 (4)	C5—C13—C14—C8	−56.7 (4)
C5—C6—C7—C8	−3.9 (5)	C12—C13—C14—C8	66.3 (4)
O3—C6—C7—O4	−3.1 (5)	C15—C13—C14—C9	59.6 (4)
C5—C6—C7—O4	−179.9 (3)	C5—C13—C14—C9	177.3 (3)
O4—C7—C8—C14	179.8 (3)	C12—C13—C14—C9	−59.7 (4)
C6—C7—C8—C14	4.4 (5)	C5—C13—C15—C16	−169.2 (3)
C17—N1—C9—C14	−173.1 (4)	C12—C13—C15—C16	63.7 (4)
C16—N1—C9—C14	60.6 (4)	C14—C13—C15—C16	−55.5 (4)
C17—N1—C9—C10	63.8 (5)	C9—N1—C16—C15	−56.4 (4)
C16—N1—C9—C10	−62.6 (4)	C17—N1—C16—C15	176.4 (4)
N1—C9—C10—C11	86.5 (4)	C13—C15—C16—N1	54.0 (4)
C14—C9—C10—C11	−36.9 (4)	C4—O2—C18—C19	−170.1 (3)
C2—C1—C11—C12	−2.1 (6)	O2—C18—C19—C24	−6.3 (5)
C2—C1—C11—C10	177.7 (4)	O2—C18—C19—C20	172.8 (3)
C9—C10—C11—C1	−177.8 (3)	C24—C19—C20—C21	3.6 (6)
C9—C10—C11—C12	2.0 (5)	C18—C19—C20—C21	−175.6 (4)
O2—C4—C12—C11	177.0 (3)	C19—C20—C21—C22	−1.0 (6)
C3—C4—C12—C11	−6.2 (5)	C20—C21—C22—C23	−1.6 (6)
O2—C4—C12—C13	−1.3 (5)	C20—C21—C22—I1	175.7 (3)
C3—C4—C12—C13	175.5 (3)	C21—C22—C23—C24	1.5 (6)
C1—C11—C12—C4	6.3 (5)	I1—C22—C23—C24	−175.9 (3)
C10—C11—C12—C4	−173.6 (3)	C22—C23—C24—C19	1.2 (6)
C1—C11—C12—C13	−175.4 (3)	C20—C19—C24—C23	−3.7 (6)
C10—C11—C12—C13	4.8 (5)	C18—C19—C24—C23	175.4 (4)
C6—C5—C13—C15	174.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5C···O3ⁱ	0.84 (3)	2.13 (3)	2.946 (5)	164 (6)
O5—H5D···N1ⁱⁱ	0.84 (3)	2.26 (11)	2.924 (6)	135 (13)

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₈INO₄·H₂O
M_r	563.41
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	8.9005 (8), 14.9221 (14), 9.2426 (9)
β (°)	91.432 (2)
V (Å³)	1227.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.34
Crystal size (mm)	0.31 × 0.30 × 0.23

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000
T_min, T_max	0.482, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7231, 5047, 4844
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.087, 1.07
No. of reflections	5047
No. of parameters	309
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.49
Absolute structure	Flack (1983), 2311 Friedel pairs
Absolute structure parameter	−0.016 (17)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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
O5—H5C···O3ⁱ	0.84 (3)	2.13 (3)	2.946 (5)	164 (6)
O5—H5D···N1ⁱⁱ	0.84 (3)	2.26 (11)	2.924 (6)	135 (13)

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

Acknowledgements

The project was supported by the National Natural Science Foundation of China (No. 20976017) and the Scientific Research Fund of Hunan Provincial Science and Technology Department of China (No. 2009 C K3070).

References

Batterham, T. J., Bell, K. H. & Weis, U. (1965). Aust. J. Chem. 18, 1799–1806. CrossRef CAS Web of Science Google Scholar
Bruker (2000). SMART, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, Y.-F., Qian, Y., Yin, L.-H., Lv, R. & Zhu, H.-J. (2009). Acta Cryst. E65, o689. CSD CrossRef IUCr Journals Google Scholar
Liu, L., Buchner, E., Beitze, D., Schmidt-Weber, C. B., Kaever, V. & Emmricinne, R. W. (1996). Int. J. Immunopharmacol. 18, 529–543. CrossRef CAS PubMed Web of Science Google Scholar
Liu, L., Riese, J., Resch, K. & Kaever, V. (1994). Arzneim. Forsch. 44, 1223–1226. CAS Google Scholar
Liu, Q., Zhou, L. L. & Li, R. (1997). Chin. Trad. Herb. Drugs, 28, 247–249. Google Scholar
Mark, W., Schneeberger, S., Seiler, R., Stroka, D. M., Amberger, A., Offner, F., Candinas, D. & Margreiter, R. (2003). Transplantation, 75, 940–945. Web of Science CrossRef PubMed CAS Google Scholar
Mitsunobu, O. (1981). Synthesis, pp. 1–28. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ye, X. R., Yan, K. X., Wu, K. M., Feng, X. Z., Huang, Y. M. & Qiu, P. (2004). Acta Pharmacol. Sin. 39, 180–183. CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(9S,13R,14S)-7,8-Dide­hydro-4-(4-iodo­benz­yl­oxy)-3,7-dimeth­­oxy-17-methyl­morphinan-6-one monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

(9S,13R,14S)-7,8-Didehydro-4-(4-iodobenzyloxy)-3,7-dimethoxy-17-methylmorphinan-6-one monohydrate