N,N′-Dimethyl-N,N′-diphenyl-3-oxa­penta­nediamide

Yin, S.; Cui, Y.; Wu, G.; You, Q.; Sun, G.

doi:10.1107/S1600536809022806

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1654

doi:10.1107/S1600536809022806

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N,N′-Dimethyl-N,N′-diphenyl-3-oxapentanediamide

Shaohong Yin,^a Yu Cui,^a Guangpu Wu,^a Qi You ^a and Guoxin Sun ^a ^*

^aSchool of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, People's Republic of China
^*Correspondence e-mail: chm_sungx@ujn.edu.cn

(Received 7 June 2009; accepted 13 June 2009; online 20 June 2009)

In the title compound, C₁₈H₂₀N₂O₃, the two phenyl rings, adopt opposite orientations in the backbone and are oriented at a dihedral angle of 36.66 (3)°. In the crystal, intermolecular C—H⋯O interactions link the molecules into a three-dimensional network.

Related literature

For a related structure, see: Zhang et al. (2001 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₂₀N₂O₃
M_r = 312.36
Monoclinic, P 2₁ /n
a = 10.7607 (11) Å
b = 10.7552 (12) Å
c = 14.7054 (14) Å
β = 102.897 (1)°
V = 1659.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.49 × 0.48 × 0.42 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.959, T_max = 0.965
8254 measured reflections
2897 independent reflections
1644 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.159
S = 1.04
2897 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O3ⁱ	0.93	2.53	3.436 (3)	165
C9—H9⋯O1ⁱⁱ	0.93	2.47	3.337 (3)	155
C12—H12B⋯O1ⁱⁱⁱ	0.96	2.48	3.346 (3)	151
C17—H17⋯O2^iv	0.93	2.52	3.432 (3)	167
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) -x+2, -y, -z; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXS97 (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/S1600536809022806/hk2708sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022806/hk2708Isup2.hkl

checkCIF report

Comment top

3-Oxapentanediamide derivatives show a highly selective complexation of lanthanide. We are interested in their performance to extract lanthanide ions. To obtain more information on the structural character and the reactivity of ligand with different lanthanide ions, we report herein the crystal structure of the title compound.

In the structure of the title compound (Fig 1), the bond lengths and angles are within normal ranges (Allen et al., 1987) and may be compared with the corresponding values in N,N'-diethyl-N,N'-diphenyl-3-oxapentanediamide (Zhang et al., 2001). The framework of the molecule is composed of a zigzag chain (C2—C1—O3—C10—C11) with two methylphenyl amide terminal groups. An interesting aspect of the molecular conformation concerns the two phenyl rings, which adopt opposite orientations in the backbone, and they are oriented at a dihedral angle of 36.66 (3)°. The moieties (O1/O3/N1/C1-C3) and (O2/N2/C10-C13) are planar [with maximum deviations of -0.036 (3) and 0.021 (3) Å for atoms C3 and C10, respectively] and the dihedral angle between them is 24.67 (3)°, which are oriented with respect to the adjacent rings A (C4-C9) and B (C13-C18) at dihedral angles of 72.97 (4) and 70.17 (3) °, respectively. Intramolecular C-H···O interactions (Table 1) result in the formation of a six-membered ring C (O1/O3/C1/C2/C10/H10B) having twisted conformation, and two five-membered rings D (O1/N1/C2/C3/H3A) and E (O2/N2/C11/C12/H12C) having envelope conformations with atoms H3A and H12C displaced by -0.415 (4) and -0.257 (5) Å. In the crystal structure, intermolecular C-H···O interactions (Table 1) link the molecules into a three-dimensional network.

Related literature top

For a related structure, see: Zhang et al. (2001). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, a solution of diglycolic chloride (10 mmol) in anhydrous benzene (3 ml) was added dropwise to a mixture of N-methylphenylamine (25 mmol), anhydrous pyridine (2 ml) in anhydrous benzene (12.5 ml) in the ice-water bath. The mixture was stirred for 3 h, and then for another 3 h at room temperature. The crude product was recrystallized from toluene as the white solid (yield; 65%, m.p. 375 K). Crystals suitable for X-ray analysis were obtained from toluene by slow evaporation over a period of several days. C₁₈H₂₀N₂O₃: C 69.21, H 6.45, N 8.97%; found: C 69.09, H 6.32, N 8.78%. IR (KBr): v = 3056, 2973, 1666, 1593, 1497, 1120, 782, 704 cm ^-1.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (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 molecule, with the atom-numbering scheme. Hydrogen bonds are shown as dashed lines.

N,N'-Dimethyl-N,N'-diphenyl-3-oxapentanediamide top

Crystal data top

C₁₈H₂₀N₂O₃	F(000) = 664
M_r = 312.36	D_x = 1.251 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1991 reflections
a = 10.7607 (11) Å	θ = 2.7–21.6°
b = 10.7552 (12) Å	µ = 0.09 mm⁻¹
c = 14.7054 (14) Å	T = 298 K
β = 102.897 (1)°	Block, yellow
V = 1659.0 (3) Å³	0.49 × 0.48 × 0.42 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2897 independent reflections
Radiation source: fine-focus sealed tube	1644 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.959, T_max = 0.965	k = −12→12
8254 measured reflections	l = −13→17

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.159	w = 1/[σ²(F_o²) + (0.0598P)² + 0.3091P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2897 reflections	Δρ_max = 0.18 e Å⁻³
209 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.090 (9)

Crystal data top

C₁₈H₂₀N₂O₃	V = 1659.0 (3) Å³
M_r = 312.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7607 (11) Å	µ = 0.09 mm⁻¹
b = 10.7552 (12) Å	T = 298 K
c = 14.7054 (14) Å	0.49 × 0.48 × 0.42 mm
β = 102.897 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2897 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1644 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.965	R_int = 0.082
8254 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.04	Δρ_max = 0.18 e Å⁻³
2897 reflections	Δρ_min = −0.17 e Å⁻³
209 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
O1	0.95256 (18)	0.09798 (18)	0.10834 (12)	0.0572 (6)
O2	0.5541 (2)	−0.1836 (2)	0.01992 (14)	0.0863 (8)
O3	0.7658 (2)	−0.05186 (17)	0.01250 (12)	0.0628 (6)
N1	0.94306 (19)	0.2313 (2)	−0.01069 (13)	0.0462 (6)
N2	0.5968 (2)	−0.1632 (2)	0.17586 (15)	0.0557 (7)
C1	0.7998 (3)	0.0548 (3)	−0.03176 (18)	0.0650 (9)
H1A	0.7254	0.1077	−0.0500	0.078*
H1B	0.8257	0.0297	−0.0881	0.078*
C2	0.9057 (2)	0.1288 (2)	0.02810 (16)	0.0446 (7)
C3	1.0382 (3)	0.3113 (3)	0.0461 (2)	0.0702 (9)
H3A	1.0361	0.3012	0.1106	0.105*
H3B	1.0202	0.3963	0.0281	0.105*
H3C	1.1211	0.2892	0.0373	0.105*
C4	0.9035 (2)	0.2600 (2)	−0.10801 (16)	0.0441 (7)
C5	0.8270 (3)	0.3608 (3)	−0.1366 (2)	0.0569 (8)
H5	0.7985	0.4094	−0.0931	0.068*
C6	0.7922 (3)	0.3901 (3)	−0.2303 (2)	0.0705 (9)
H6	0.7404	0.4587	−0.2496	0.085*
C7	0.8333 (3)	0.3192 (3)	−0.2946 (2)	0.0664 (9)
H7	0.8093	0.3393	−0.3576	0.080*
C8	0.9092 (3)	0.2192 (3)	−0.26665 (19)	0.0607 (8)
H8	0.9370	0.1708	−0.3107	0.073*
C9	0.9458 (3)	0.1887 (3)	−0.17269 (18)	0.0527 (7)
H9	0.9985	0.1207	−0.1536	0.063*
C10	0.7034 (3)	−0.0267 (3)	0.08526 (18)	0.0586 (8)
H10A	0.6570	0.0510	0.0734	0.070*
H10B	0.7655	−0.0194	0.1440	0.070*
C11	0.6129 (3)	−0.1313 (3)	0.09046 (19)	0.0546 (8)
C12	0.5068 (3)	−0.2618 (3)	0.1840 (2)	0.0853 (11)
H12A	0.4299	−0.2257	0.1951	0.128*
H12B	0.5438	−0.3154	0.2350	0.128*
H12C	0.4873	−0.3090	0.1272	0.128*
C13	0.6656 (2)	−0.1065 (3)	0.26044 (17)	0.0462 (7)
C14	0.6387 (3)	0.0131 (3)	0.2830 (2)	0.0600 (8)
H14	0.5744	0.0576	0.2437	0.072*
C15	0.7064 (3)	0.0669 (3)	0.3633 (2)	0.0710 (9)
H15	0.6894	0.1485	0.3775	0.085*
C16	0.7991 (3)	0.0009 (4)	0.4227 (2)	0.0725 (10)
H16	0.8451	0.0376	0.4772	0.087*
C17	0.8238 (3)	−0.1183 (3)	0.4018 (2)	0.0695 (9)
H17	0.8863	−0.1634	0.4424	0.083*
C18	0.7570 (3)	−0.1728 (3)	0.32081 (19)	0.0571 (8)
H18	0.7739	−0.2546	0.3071	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0702 (13)	0.0581 (13)	0.0402 (11)	−0.0074 (10)	0.0056 (9)	0.0084 (9)
O2	0.1040 (18)	0.0934 (18)	0.0524 (13)	−0.0513 (15)	−0.0021 (12)	0.0040 (11)
O3	0.0947 (16)	0.0526 (12)	0.0479 (11)	−0.0247 (11)	0.0302 (10)	−0.0064 (9)
N1	0.0509 (13)	0.0468 (14)	0.0388 (12)	−0.0111 (11)	0.0058 (9)	0.0034 (10)
N2	0.0516 (14)	0.0659 (16)	0.0478 (14)	−0.0184 (12)	0.0072 (10)	0.0103 (11)
C1	0.083 (2)	0.067 (2)	0.0435 (16)	−0.0325 (18)	0.0119 (15)	0.0048 (14)
C2	0.0552 (16)	0.0431 (16)	0.0366 (14)	−0.0029 (14)	0.0128 (12)	0.0022 (12)
C3	0.079 (2)	0.072 (2)	0.0536 (18)	−0.0309 (18)	0.0008 (15)	0.0019 (15)
C4	0.0427 (14)	0.0477 (17)	0.0411 (14)	−0.0096 (13)	0.0076 (11)	0.0079 (12)
C5	0.0528 (17)	0.0564 (19)	0.0620 (18)	0.0019 (15)	0.0139 (13)	0.0108 (15)
C6	0.060 (2)	0.077 (2)	0.071 (2)	0.0115 (18)	0.0072 (16)	0.0285 (18)
C7	0.063 (2)	0.080 (2)	0.0493 (18)	−0.0150 (19)	−0.0014 (15)	0.0205 (17)
C8	0.072 (2)	0.066 (2)	0.0464 (16)	−0.0141 (18)	0.0179 (14)	0.0011 (15)
C9	0.0584 (17)	0.0523 (18)	0.0487 (16)	−0.0005 (14)	0.0145 (13)	0.0074 (13)
C10	0.077 (2)	0.0569 (19)	0.0455 (16)	−0.0217 (16)	0.0215 (14)	−0.0025 (13)
C11	0.0559 (17)	0.0565 (19)	0.0474 (16)	−0.0150 (15)	0.0026 (13)	0.0071 (14)
C12	0.079 (2)	0.103 (3)	0.072 (2)	−0.045 (2)	0.0125 (17)	0.0183 (19)
C13	0.0412 (15)	0.0555 (18)	0.0448 (15)	−0.0020 (13)	0.0157 (12)	0.0087 (13)
C14	0.0534 (18)	0.066 (2)	0.0649 (19)	0.0166 (16)	0.0217 (15)	0.0113 (16)
C15	0.087 (3)	0.066 (2)	0.069 (2)	0.0054 (19)	0.037 (2)	−0.0047 (18)
C16	0.084 (2)	0.086 (3)	0.0507 (18)	−0.010 (2)	0.0202 (17)	−0.0075 (18)
C17	0.069 (2)	0.085 (3)	0.0507 (18)	0.0095 (19)	0.0052 (15)	0.0092 (17)
C18	0.0613 (18)	0.0565 (19)	0.0524 (17)	0.0149 (15)	0.0100 (14)	0.0088 (14)

Geometric parameters (Å, º) top

O1—C2	1.221 (3)	C7—C8	1.358 (4)
O2—C11	1.225 (3)	C7—H7	0.9300
O3—C1	1.407 (3)	C8—C9	1.389 (4)
O3—C10	1.410 (3)	C8—H8	0.9300
N1—C2	1.343 (3)	C9—H9	0.9300
N1—C4	1.433 (3)	C10—C11	1.501 (4)
N1—C3	1.450 (3)	C10—H10A	0.9700
N2—C11	1.350 (3)	C10—H10B	0.9700
N2—C13	1.434 (3)	C12—H12A	0.9600
N2—C12	1.459 (4)	C12—H12B	0.9600
C1—C2	1.504 (4)	C12—H12C	0.9600
C1—H1A	0.9700	C13—C18	1.369 (4)
C1—H1B	0.9700	C13—C14	1.376 (4)
C3—H3A	0.9600	C14—C15	1.369 (4)
C3—H3B	0.9600	C14—H14	0.9300
C3—H3C	0.9600	C15—C16	1.368 (4)
C4—C5	1.370 (4)	C15—H15	0.9300
C4—C9	1.376 (4)	C16—C17	1.359 (5)
C5—C6	1.381 (4)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.377 (4)
C6—C7	1.363 (4)	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300

C1—O3—C10	114.3 (2)	C4—C9—C8	119.5 (3)
C2—N1—C4	123.4 (2)	C4—C9—H9	120.2
C2—N1—C3	118.8 (2)	C8—C9—H9	120.2
C4—N1—C3	117.5 (2)	O3—C10—C11	108.6 (2)
C11—N2—C13	123.4 (2)	O3—C10—H10A	110.0
C11—N2—C12	119.1 (2)	C11—C10—H10A	110.0
C13—N2—C12	117.5 (2)	O3—C10—H10B	110.0
O3—C1—C2	113.7 (2)	C11—C10—H10B	110.0
O3—C1—H1A	108.8	H10A—C10—H10B	108.3
C2—C1—H1A	108.8	O2—C11—N2	121.5 (3)
O3—C1—H1B	108.8	O2—C11—C10	121.3 (2)
C2—C1—H1B	108.8	N2—C11—C10	117.2 (2)
H1A—C1—H1B	107.7	N2—C12—H12A	109.5
O1—C2—N1	122.4 (2)	N2—C12—H12B	109.5
O1—C2—C1	121.2 (2)	H12A—C12—H12B	109.5
N1—C2—C1	116.5 (2)	N2—C12—H12C	109.5
N1—C3—H3A	109.5	H12A—C12—H12C	109.5
N1—C3—H3B	109.5	H12B—C12—H12C	109.5
H3A—C3—H3B	109.5	C18—C13—C14	119.3 (3)
N1—C3—H3C	109.5	C18—C13—N2	119.9 (3)
H3A—C3—H3C	109.5	C14—C13—N2	120.8 (2)
H3B—C3—H3C	109.5	C15—C14—C13	120.2 (3)
C5—C4—C9	119.8 (2)	C15—C14—H14	119.9
C5—C4—N1	120.1 (2)	C13—C14—H14	119.9
C9—C4—N1	120.0 (2)	C16—C15—C14	120.2 (3)
C4—C5—C6	119.8 (3)	C16—C15—H15	119.9
C4—C5—H5	120.1	C14—C15—H15	119.9
C6—C5—H5	120.1	C17—C16—C15	119.8 (3)
C7—C6—C5	120.5 (3)	C17—C16—H16	120.1
C7—C6—H6	119.7	C15—C16—H16	120.1
C5—C6—H6	119.7	C16—C17—C18	120.4 (3)
C8—C7—C6	119.9 (3)	C16—C17—H17	119.8
C8—C7—H7	120.0	C18—C17—H17	119.8
C6—C7—H7	120.0	C13—C18—C17	120.0 (3)
C7—C8—C9	120.4 (3)	C13—C18—H18	120.0
C7—C8—H8	119.8	C17—C18—H18	120.0
C9—C8—H8	119.8

C10—O3—C1—C2	70.1 (3)	C1—O3—C10—C11	149.2 (2)
C4—N1—C2—O1	170.6 (2)	C13—N2—C11—O2	178.6 (3)
C3—N1—C2—O1	−2.9 (4)	C12—N2—C11—O2	−0.4 (4)
C4—N1—C2—C1	−11.0 (4)	C13—N2—C11—C10	−2.9 (4)
C3—N1—C2—C1	175.4 (3)	C12—N2—C11—C10	178.1 (3)
O3—C1—C2—O1	−2.1 (4)	O3—C10—C11—O2	−36.2 (4)
O3—C1—C2—N1	179.5 (2)	O3—C10—C11—N2	145.2 (3)
C2—N1—C4—C5	113.5 (3)	C11—N2—C13—C18	−109.3 (3)
C3—N1—C4—C5	−72.9 (3)	C12—N2—C13—C18	69.7 (3)
C2—N1—C4—C9	−68.7 (3)	C11—N2—C13—C14	72.3 (3)
C3—N1—C4—C9	104.9 (3)	C12—N2—C13—C14	−108.7 (3)
C9—C4—C5—C6	0.3 (4)	C18—C13—C14—C15	2.6 (4)
N1—C4—C5—C6	178.1 (2)	N2—C13—C14—C15	−179.0 (2)
C4—C5—C6—C7	0.1 (4)	C13—C14—C15—C16	−1.6 (4)
C5—C6—C7—C8	−0.2 (5)	C14—C15—C16—C17	−0.1 (5)
C6—C7—C8—C9	−0.2 (4)	C15—C16—C17—C18	0.6 (5)
C5—C4—C9—C8	−0.7 (4)	C14—C13—C18—C17	−2.1 (4)
N1—C4—C9—C8	−178.5 (2)	N2—C13—C18—C17	179.5 (2)
C7—C8—C9—C4	0.6 (4)	C16—C17—C18—C13	0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1	0.96	2.36	2.707 (3)	101
C7—H7···O3ⁱ	0.93	2.53	3.436 (3)	165
C9—H9···O1ⁱⁱ	0.93	2.47	3.337 (3)	155
C10—H10B···O1	0.97	2.53	2.949 (3)	106
C12—H12B···O1ⁱⁱⁱ	0.96	2.48	3.346 (3)	151
C12—H12C···O2	0.96	2.31	2.709 (3)	104
C17—H17···O2^iv	0.93	2.52	3.432 (3)	167

Symmetry codes: (i) −x+3/2, y+1/2, −z−1/2; (ii) −x+2, −y, −z; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x+1/2, −y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₃
M_r	312.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.7607 (11), 10.7552 (12), 14.7054 (14)
β (°)	102.897 (1)
V (Å³)	1659.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.49 × 0.48 × 0.42

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.959, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	8254, 2897, 1644
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.159, 1.04
No. of reflections	2897
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.17

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1	0.96	2.36	2.707 (3)	101
C7—H7···O3ⁱ	0.93	2.53	3.436 (3)	165
C9—H9···O1ⁱⁱ	0.93	2.47	3.337 (3)	155
C10—H10B···O1	0.97	2.53	2.949 (3)	106
C12—H12B···O1ⁱⁱⁱ	0.96	2.48	3.346 (3)	151
C12—H12C···O2	0.96	2.31	2.709 (3)	104
C17—H17···O2^iv	0.93	2.52	3.432 (3)	167

Symmetry codes: (i) −x+3/2, y+1/2, −z−1/2; (ii) −x+2, −y, −z; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x+1/2, −y−1/2, z+1/2.

Acknowledgements

The authors thank the National Science Foundation of China (grant No. 203010008), the Science Foundation of Shandong Province (grant No. Q2003B01) and Key Subject Research Foundation of Shandong Province for support of this work.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Y.-L., Wang, Y.-W., Li, Y.-Z., Liu, W.-S., Yu, K.-B. & Wang, L.-F. (2001). Acta Cryst. E57, o483–o484. Web of Science CSD CrossRef IUCr Journals Google Scholar