4-[Bis(3,4-dimethoxy­phen­yl)meth­yl]pyridine ethanol monosolvate

Jian, F.-F.; Ni, Z.-P.

doi:10.1107/S1600536810017460

organic compounds

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Volume 66| Part 6| June 2010| Page o1378

https://doi.org/10.1107/S1600536810017460

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4-[Bis(3,4-dimethoxyphenyl)methyl]pyridine ethanol monosolvate

Fang-Fang Jian ^a ^* and Zhi-Peng Ni ^a

^aNew Materials and Function Coordination Chemistry Laboratory, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: ffj2003@163169.net

(Received 10 May 2010; accepted 12 May 2010; online 19 May 2010)

In the title compound, C₂₂H₂₃NO₄·C₂H₆O, the pyridyl ring is aligned at 89.39 (2) and 87.41 (2)° with respect to the benzene rings, and the three rings connected to the methine C atom are arranged in a propeller-like conformation. The heterocycle is linked to the solvent molecule by an O—H⋯N hydrogen bond.

Related literature

For background to the use of pyridine and its derivatives as ligands to bridge different metal ions and form functional coordination compounds, see: Chen et al. (2007 ); Fasina et al. (2004 ); Mancisidor et al. (2008 ). For the synthesis, see: Ostaszewski (1998 ).

Experimental

Crystal data

C₂₂H₂₃NO₄·C₂H₆O
M_r = 411.48
Monoclinic, C 2/c
a = 29.564 (6) Å
b = 8.3810 (17) Å
c = 19.440 (4) Å
β = 107.94 (3)°
V = 4582.6 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.27 × 0.20 × 0.19 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
14513 measured reflections
5573 independent reflections
2669 reflections with I > 2σ(I)
R_int = 0.042
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.174
S = 1.02
5573 reflections
277 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N1	0.82	2.04	2.842 (4)	167

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ); 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: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810017460/ng2771sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810017460/ng2771Isup2.hkl

checkCIF report

Comment top

Pyridine and its derivatives, are of interest as ligands to bridge different metal ions to form functional coordination compounds, for example: 9,10-bis(4'- pyridylethynyl)-anthracene (Fasina et al., 2004);2,6-bis-(imi-dazol-1 -yl)pyridine (Chen et al., 2007); bis-(pyridine-2-ylmethyl)-benzylamine (Mancisidor et al., 2008). In order to search for new pyridine compounds with higher bioactivity and optical properties, we synthesized the title compound.

In the title compound, the bond lengths and angles are generally normal. The dihedral angles between pyridine ring N1, C20, C19, C18, C22, C21(p1) with C3—C8 (p2) phenyl ring and C10—C15 (p3) phenyl ring are 89.39 (2)° and 87.41 (2)°, the dihedral angles between C3—C8 (p2) phenyl ring and C10—C15 (p3) phenyl ring is 84.33 (2)°, respectively.

The crystal structure is stabilized by intramolecular O—H···N hydrogen bonds (Table 1) and intramolecular C—H···O hydrogen bonds. The donor and acceptor distance are 3.4019Å for C(20) – H(20 A).. O(5) and 3.3902Å for C(21) – H(21 A).. O(3). In addition, there exist four kinds of C—H···Π interaction in the lattice [C2···Cg1=3.441 (2) Å; C3···Cg2=4.052 (3) Å; C17···Cg2=3.774 (2) Å; C24···Cg3=4.187 (1) Å; Cg1, Cg2 and Cg3 refer to pyridine, phenyl C3—C8 and phenyl ring C10—C15, respectively]. In the solid state, all above intermolecular interactions in the title compound stabilize the crystal packing structure.

Related literature top

For background to the use of pyridine and its derivatives as ligands to bridge

different metal ions and form functional coordination compounds, see: Chen et al. (2007); Fasina et al. (2004); Mancisidor et al. (2008). For the synthesis, see: Ostaszewski (1998).

Experimental top

The title compound was prepared by the reaction of 1,2-dimethoxybenzene (20 mmol), isonicotinaldehyde (40 mmol), and was stirred in dichloromethane solution with 84% sulfuric acid (10 ml) as activator (Ostaszewski et al., 1998). Single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature over a period of 3 days.

Structure description top

For background to the use of pyridine and its derivatives as ligands to bridge

different metal ions and form functional coordination compounds, see: Chen et al. (2007); Fasina et al. (2004); Mancisidor et al. (2008). For the synthesis, see: Ostaszewski (1998).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); 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: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.

4-[Bis(3,4-dimethoxyphenyl)methyl]pyridine ethanol monosolvate top

Crystal data top

C₂₂H₂₃NO₄·C₂H₆O	F(000) = 1760
M_r = 411.48	D_x = 1.193 Mg m⁻³
Monoclinic, C2/c	Melting point: 342 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 29.564 (6) Å	Cell parameters from 25 reflections
b = 8.3810 (17) Å	θ = 1.5–25.5°
c = 19.440 (4) Å	µ = 0.08 mm⁻¹
β = 107.94 (3)°	T = 295 K
V = 4582.6 (18) Å³	Block, colourless
Z = 8	0.27 × 0.20 × 0.19 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.042
Radiation source: fine-focus sealed tube	θ_max = 28.3°, θ_min = 1.5°
Graphite monochromator	h = −34→38
ω scans	k = −11→10
14513 measured reflections	l = −25→20
5573 independent reflections	3 standard reflections every 100 reflections
2669 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.070P)² + 0.6422P] where P = (F_o² + 2F_c²)/3
5573 reflections	(Δ/σ)_max < 0.001
277 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₂H₂₃NO₄·C₂H₆O	V = 4582.6 (18) Å³
M_r = 411.48	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.564 (6) Å	µ = 0.08 mm⁻¹
b = 8.3810 (17) Å	T = 295 K
c = 19.440 (4) Å	0.27 × 0.20 × 0.19 mm
β = 107.94 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.042
14513 measured reflections	3 standard reflections every 100 reflections
5573 independent reflections	intensity decay: none
2669 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.02	Δρ_max = 0.22 e Å⁻³
5573 reflections	Δρ_min = −0.22 e Å⁻³
277 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.30498 (6)	1.1065 (2)	0.93614 (10)	0.0848 (6)
O2	0.23104 (6)	1.2671 (2)	0.86968 (10)	0.0795 (5)
O3	0.07275 (6)	1.2438 (2)	0.48851 (8)	0.0711 (5)
O4	0.15262 (5)	1.1115 (2)	0.49173 (8)	0.0648 (5)
O5	0.02886 (9)	0.3191 (3)	0.87938 (15)	0.1157 (8)
H5	0.0360	0.3742	0.8494	0.139*
N1	0.06698 (8)	0.5258 (3)	0.79531 (13)	0.0770 (6)
C1	0.34474 (13)	1.0218 (4)	0.97716 (19)	0.1275 (14)
H1B	0.3659	1.0926	1.0109	0.191*
H1C	0.3608	0.9765	0.9458	0.191*
H1D	0.3349	0.9380	1.0030	0.191*
C2	0.19141 (11)	1.3623 (4)	0.83401 (19)	0.1037 (11)
H2A	0.1957	1.4676	0.8544	0.156*
H2B	0.1631	1.3158	0.8399	0.156*
H2C	0.1884	1.3683	0.7835	0.156*
C3	0.24084 (8)	0.8041 (3)	0.80555 (12)	0.0592 (6)
H3A	0.2443	0.6994	0.7922	0.071*
C4	0.27668 (8)	0.8747 (3)	0.86124 (13)	0.0627 (7)
H4A	0.3039	0.8167	0.8845	0.075*
C5	0.27240 (8)	1.0275 (3)	0.88221 (12)	0.0573 (6)
C6	0.23211 (8)	1.1147 (3)	0.84613 (12)	0.0550 (6)
C7	0.19656 (8)	1.0447 (3)	0.79090 (12)	0.0546 (6)
H7A	0.1696	1.1034	0.7672	0.066*
C8	0.20042 (7)	0.8876 (3)	0.77007 (11)	0.0491 (5)
C9	0.16086 (7)	0.8074 (3)	0.71137 (10)	0.0503 (6)
H9A	0.1764	0.7297	0.6884	0.060*
C10	0.13455 (7)	0.9216 (3)	0.65203 (11)	0.0493 (5)
C11	0.09260 (8)	0.9934 (3)	0.64980 (12)	0.0608 (7)
H11A	0.0783	0.9687	0.6849	0.073*
C12	0.07107 (8)	1.1021 (3)	0.59624 (12)	0.0626 (7)
H12A	0.0427	1.1508	0.5960	0.075*
C13	0.09124 (8)	1.1383 (3)	0.54365 (11)	0.0528 (6)
C14	0.13426 (7)	1.0673 (3)	0.54553 (11)	0.0481 (5)
C15	0.15522 (7)	0.9611 (3)	0.59909 (11)	0.0486 (5)
H15A	0.1839	0.9142	0.6002	0.058*
C16	0.02736 (11)	1.3087 (4)	0.48086 (18)	0.1096 (12)
H16A	0.0186	1.3801	0.4403	0.164*
H16B	0.0282	1.3659	0.5240	0.164*
H16C	0.0045	1.2240	0.4731	0.164*
C17	0.19682 (9)	1.0437 (3)	0.49298 (14)	0.0800 (8)
H17A	0.2065	1.0867	0.4540	0.120*
H17B	0.1935	0.9300	0.4877	0.120*
H17C	0.2203	1.0683	0.5382	0.120*
C18	0.12750 (8)	0.7117 (3)	0.74155 (11)	0.0517 (6)
C19	0.09979 (10)	0.5923 (3)	0.70163 (13)	0.0783 (8)
H19A	0.1008	0.5715	0.6551	0.094*
C20	0.07074 (11)	0.5034 (4)	0.72947 (17)	0.0918 (9)
H20A	0.0527	0.4231	0.7009	0.110*
C21	0.09305 (9)	0.6417 (3)	0.83336 (14)	0.0657 (7)
H21A	0.0909	0.6613	0.8793	0.079*
C22	0.12338 (8)	0.7359 (3)	0.80920 (12)	0.0566 (6)
H22A	0.1410	0.8157	0.8388	0.068*
C23	0.0512 (2)	0.0797 (6)	0.8412 (3)	0.227 (3)
H23A	0.0652	−0.0205	0.8605	0.340*
H23B	0.0658	0.1179	0.8066	0.340*
H23C	0.0177	0.0656	0.8181	0.340*
C24	0.05815 (13)	0.1877 (5)	0.8959 (2)	0.1247 (13)
H24A	0.0909	0.2236	0.9096	0.150*
H24B	0.0534	0.1345	0.9374	0.150*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0727 (12)	0.0672 (12)	0.0895 (12)	−0.0157 (10)	−0.0119 (10)	0.0122 (10)
O2	0.0763 (13)	0.0534 (11)	0.0964 (13)	−0.0007 (9)	0.0085 (10)	−0.0037 (10)
O3	0.0654 (11)	0.0860 (12)	0.0681 (10)	0.0276 (10)	0.0297 (8)	0.0295 (9)
O4	0.0664 (11)	0.0799 (12)	0.0586 (9)	0.0179 (9)	0.0346 (8)	0.0171 (8)
O5	0.1304 (19)	0.0829 (16)	0.164 (2)	0.0193 (15)	0.0893 (17)	0.0368 (15)
N1	0.0741 (15)	0.0770 (16)	0.0810 (15)	−0.0157 (13)	0.0257 (12)	0.0058 (13)
C1	0.105 (3)	0.105 (3)	0.121 (3)	−0.007 (2)	−0.041 (2)	0.014 (2)
C2	0.089 (2)	0.0649 (19)	0.142 (3)	0.0179 (17)	0.013 (2)	−0.011 (2)
C3	0.0556 (15)	0.0595 (15)	0.0647 (14)	0.0085 (12)	0.0216 (12)	0.0095 (12)
C4	0.0476 (14)	0.0656 (17)	0.0708 (16)	0.0053 (12)	0.0124 (12)	0.0195 (14)
C5	0.0500 (14)	0.0582 (16)	0.0595 (14)	−0.0057 (12)	0.0107 (11)	0.0165 (12)
C6	0.0540 (15)	0.0517 (15)	0.0606 (14)	−0.0043 (12)	0.0193 (12)	0.0083 (12)
C7	0.0482 (14)	0.0567 (15)	0.0602 (14)	0.0032 (11)	0.0185 (11)	0.0127 (12)
C8	0.0457 (13)	0.0568 (15)	0.0484 (12)	0.0034 (11)	0.0198 (10)	0.0106 (11)
C9	0.0535 (13)	0.0549 (14)	0.0457 (12)	0.0080 (11)	0.0201 (10)	0.0036 (10)
C10	0.0512 (13)	0.0551 (14)	0.0438 (11)	0.0057 (11)	0.0179 (10)	0.0021 (10)
C11	0.0583 (15)	0.0809 (18)	0.0514 (13)	0.0138 (13)	0.0289 (11)	0.0143 (12)
C12	0.0506 (14)	0.0802 (18)	0.0621 (14)	0.0187 (13)	0.0247 (12)	0.0134 (13)
C13	0.0518 (14)	0.0593 (14)	0.0481 (12)	0.0068 (11)	0.0163 (10)	0.0071 (11)
C14	0.0488 (13)	0.0541 (13)	0.0448 (11)	0.0023 (11)	0.0194 (10)	−0.0013 (10)
C15	0.0458 (12)	0.0539 (14)	0.0486 (12)	0.0060 (11)	0.0185 (10)	−0.0020 (11)
C16	0.086 (2)	0.139 (3)	0.117 (2)	0.061 (2)	0.0505 (19)	0.065 (2)
C17	0.0815 (19)	0.100 (2)	0.0775 (17)	0.0284 (17)	0.0530 (15)	0.0195 (16)
C18	0.0519 (13)	0.0559 (14)	0.0465 (12)	0.0020 (11)	0.0141 (10)	0.0031 (11)
C19	0.094 (2)	0.088 (2)	0.0525 (14)	−0.0251 (17)	0.0221 (14)	−0.0119 (14)
C20	0.097 (2)	0.094 (2)	0.081 (2)	−0.0386 (18)	0.0223 (17)	−0.0097 (17)
C21	0.0691 (17)	0.0713 (17)	0.0635 (15)	−0.0018 (15)	0.0304 (13)	0.0059 (14)
C22	0.0624 (15)	0.0562 (14)	0.0543 (13)	−0.0049 (12)	0.0224 (11)	−0.0031 (11)
C23	0.330 (9)	0.152 (5)	0.213 (6)	0.083 (6)	0.107 (6)	−0.038 (4)
C24	0.090 (3)	0.126 (4)	0.152 (4)	0.010 (2)	0.029 (2)	0.031 (3)

Geometric parameters (Å, º) top

O1—C5	1.358 (3)	C9—H9A	0.9800
O1—C1	1.395 (3)	C10—C11	1.367 (3)
O2—C6	1.361 (3)	C10—C15	1.389 (3)
O2—C2	1.410 (3)	C11—C12	1.383 (3)
O3—C13	1.367 (3)	C11—H11A	0.9300
O3—C16	1.413 (3)	C12—C13	1.367 (3)
O4—C14	1.369 (2)	C12—H12A	0.9300
O4—C17	1.418 (3)	C13—C14	1.395 (3)
O5—C24	1.377 (4)	C14—C15	1.365 (3)
O5—H5	0.8200	C15—H15A	0.9300
N1—C21	1.317 (3)	C16—H16A	0.9600
N1—C20	1.332 (3)	C16—H16B	0.9600
C1—H1B	0.9600	C16—H16C	0.9600
C1—H1C	0.9600	C17—H17A	0.9600
C1—H1D	0.9600	C17—H17B	0.9600
C2—H2A	0.9600	C17—H17C	0.9600
C2—H2B	0.9600	C18—C19	1.373 (3)
C2—H2C	0.9600	C18—C22	1.373 (3)
C3—C8	1.373 (3)	C19—C20	1.368 (4)
C3—C4	1.392 (3)	C19—H19A	0.9300
C3—H3A	0.9300	C20—H20A	0.9300
C4—C5	1.362 (3)	C21—C22	1.381 (3)
C4—H4A	0.9300	C21—H21A	0.9300
C5—C6	1.389 (3)	C22—H22A	0.9300
C6—C7	1.381 (3)	C23—C24	1.362 (5)
C7—C8	1.392 (3)	C23—H23A	0.9600
C7—H7A	0.9300	C23—H23B	0.9600
C8—C9	1.517 (3)	C23—H23C	0.9600
C9—C10	1.516 (3)	C24—H24A	0.9700
C9—C18	1.522 (3)	C24—H24B	0.9700

C5—O1—C1	117.8 (2)	C11—C12—H12A	119.9
C6—O2—C2	117.9 (2)	C12—C13—O3	124.7 (2)
C13—O3—C16	117.95 (19)	C12—C13—C14	119.4 (2)
C14—O4—C17	117.27 (18)	O3—C13—C14	115.96 (19)
C24—O5—H5	109.5	C15—C14—O4	124.44 (19)
C21—N1—C20	115.9 (2)	C15—C14—C13	119.63 (19)
O1—C1—H1B	109.5	O4—C14—C13	115.93 (19)
O1—C1—H1C	109.5	C14—C15—C10	121.4 (2)
H1B—C1—H1C	109.5	C14—C15—H15A	119.3
O1—C1—H1D	109.5	C10—C15—H15A	119.3
H1B—C1—H1D	109.5	O3—C16—H16A	109.5
H1C—C1—H1D	109.5	O3—C16—H16B	109.5
O2—C2—H2A	109.5	H16A—C16—H16B	109.5
O2—C2—H2B	109.5	O3—C16—H16C	109.5
H2A—C2—H2B	109.5	H16A—C16—H16C	109.5
O2—C2—H2C	109.5	H16B—C16—H16C	109.5
H2A—C2—H2C	109.5	O4—C17—H17A	109.5
H2B—C2—H2C	109.5	O4—C17—H17B	109.5
C8—C3—C4	120.7 (2)	H17A—C17—H17B	109.5
C8—C3—H3A	119.7	O4—C17—H17C	109.5
C4—C3—H3A	119.7	H17A—C17—H17C	109.5
C5—C4—C3	120.9 (2)	H17B—C17—H17C	109.5
C5—C4—H4A	119.5	C19—C18—C22	115.8 (2)
C3—C4—H4A	119.5	C19—C18—C9	120.7 (2)
O1—C5—C4	125.5 (2)	C22—C18—C9	123.4 (2)
O1—C5—C6	115.3 (2)	C20—C19—C18	120.8 (2)
C4—C5—C6	119.2 (2)	C20—C19—H19A	119.6
O2—C6—C7	124.7 (2)	C18—C19—H19A	119.6
O2—C6—C5	115.4 (2)	N1—C20—C19	123.5 (3)
C7—C6—C5	119.9 (2)	N1—C20—H20A	118.2
C6—C7—C8	121.1 (2)	C19—C20—H20A	118.2
C6—C7—H7A	119.4	N1—C21—C22	124.0 (2)
C8—C7—H7A	119.4	N1—C21—H21A	118.0
C3—C8—C7	118.2 (2)	C22—C21—H21A	118.0
C3—C8—C9	120.1 (2)	C18—C22—C21	120.0 (2)
C7—C8—C9	121.67 (19)	C18—C22—H22A	120.0
C10—C9—C8	112.84 (19)	C21—C22—H22A	120.0
C10—C9—C18	112.59 (18)	C24—C23—H23A	109.5
C8—C9—C18	112.63 (16)	C24—C23—H23B	109.5
C10—C9—H9A	106.0	H23A—C23—H23B	109.5
C8—C9—H9A	106.0	C24—C23—H23C	109.5
C18—C9—H9A	106.0	H23A—C23—H23C	109.5
C11—C10—C15	118.3 (2)	H23B—C23—H23C	109.5
C11—C10—C9	123.36 (19)	C23—C24—O5	114.7 (4)
C15—C10—C9	118.31 (19)	C23—C24—H24A	108.6
C10—C11—C12	121.1 (2)	O5—C24—H24A	108.6
C10—C11—H11A	119.4	C23—C24—H24B	108.6
C12—C11—H11A	119.4	O5—C24—H24B	108.6
C13—C12—C11	120.2 (2)	H24A—C24—H24B	107.6
C13—C12—H12A	119.9

C8—C3—C4—C5	0.5 (3)	C10—C11—C12—C13	0.8 (4)
C1—O1—C5—C4	−4.8 (4)	C11—C12—C13—O3	180.0 (2)
C1—O1—C5—C6	176.1 (3)	C11—C12—C13—C14	−1.5 (4)
C3—C4—C5—O1	179.4 (2)	C16—O3—C13—C12	−6.5 (4)
C3—C4—C5—C6	−1.5 (3)	C16—O3—C13—C14	174.9 (2)
C2—O2—C6—C7	−1.8 (4)	C17—O4—C14—C15	−1.1 (3)
C2—O2—C6—C5	178.7 (2)	C17—O4—C14—C13	178.8 (2)
O1—C5—C6—O2	0.3 (3)	C12—C13—C14—C15	1.0 (3)
C4—C5—C6—O2	−178.9 (2)	O3—C13—C14—C15	179.7 (2)
O1—C5—C6—C7	−179.3 (2)	C12—C13—C14—O4	−178.9 (2)
C4—C5—C6—C7	1.5 (3)	O3—C13—C14—O4	−0.2 (3)
O2—C6—C7—C8	−180.0 (2)	O4—C14—C15—C10	−180.0 (2)
C5—C6—C7—C8	−0.5 (3)	C13—C14—C15—C10	0.1 (3)
C4—C3—C8—C7	0.6 (3)	C11—C10—C15—C14	−0.7 (3)
C4—C3—C8—C9	−177.74 (19)	C9—C10—C15—C14	−177.8 (2)
C6—C7—C8—C3	−0.6 (3)	C10—C9—C18—C19	72.2 (3)
C6—C7—C8—C9	177.71 (19)	C8—C9—C18—C19	−158.8 (2)
C3—C8—C9—C10	−147.48 (19)	C10—C9—C18—C22	−108.8 (2)
C7—C8—C9—C10	34.3 (3)	C8—C9—C18—C22	20.2 (3)
C3—C8—C9—C18	83.7 (2)	C22—C18—C19—C20	−0.9 (4)
C7—C8—C9—C18	−94.6 (2)	C9—C18—C19—C20	178.2 (3)
C8—C9—C10—C11	−97.2 (3)	C21—N1—C20—C19	0.5 (4)
C18—C9—C10—C11	31.7 (3)	C18—C19—C20—N1	0.4 (5)
C8—C9—C10—C15	79.6 (2)	C20—N1—C21—C22	−0.9 (4)
C18—C9—C10—C15	−151.5 (2)	C19—C18—C22—C21	0.5 (3)
C15—C10—C11—C12	0.2 (4)	C9—C18—C22—C21	−178.5 (2)
C9—C10—C11—C12	177.1 (2)	N1—C21—C22—C18	0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N1	0.82	2.04	2.842 (4)	167

Experimental details

Crystal data
Chemical formula	C₂₂H₂₃NO₄·C₂H₆O
M_r	411.48
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	29.564 (6), 8.3810 (17), 19.440 (4)
β (°)	107.94 (3)
V (Å³)	4582.6 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.27 × 0.20 × 0.19

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14513, 5573, 2669
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.174, 1.02
No. of reflections	5573
No. of parameters	277
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N1	0.82	2.04	2.842 (4)	167

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province (No. Z2007B01).

References

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