4,4,5,5-Tetra­methyl-2-[(Z)-1-(3-methyl­phenoxy)hex-1-en-2-yl]-1,3,2-dioxaborolane

Li, K.-X.; Wang, X.-J.

doi:10.1107/S2414314616006118

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160611

doi:10.1107/S2414314616006118

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4,4,5,5-Tetramethyl-2-[(Z)-1-(3-methylphenoxy)hex-1-en-2-yl]-1,3,2-dioxaborolane

Kai-Xiao Li ^a and Xiao-Juan Wang ^b ^*

^aCollege of Physical Education and Health Sciences, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China, and ^bCollege of Chemistry and Life Science, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: wangxj@zjnu.cn

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 16 March 2016; accepted 12 April 2016; online 19 April 2016)

The title compound, C₁₉H₂₉BO₃, was prepared by the reaction of 1-(hex-1-yn-1-yloxy)-3-methylbenzene in tetrahydrofuran with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane under a nitrogen atmosphere. In the molecule, the butyl group adopts an extended conformation, with a torsion angle of 179.52 (19)°. The dioxaborolane ring has a twisted conformation on the C—C bond, and its mean plane is inclined to the 3-methylphenyl ring by 44.79 (19)°. In the crystal, there are no significant intermolecular interactions present.

Keywords: crystal structure; dioxaborolane; extended conformation.

CCDC reference: 1473545

3D view (loading...)

Chemical scheme

Structure description

The title compound was previously prepared by Cui et al. (2013 ), and its derivatives were synthesized by Yang & Cheng (2001 ) and Whelligan et al. (2010 ). We present here the crystal structure of the compound (Fig. 1). In the molecule, the conformation of the dioxaborolane ring is similar to half chair, and the butyl group adopts an extended conformation with a C10—C11—C12—C13 torsion angle = 179.52 (19)°. No hydrogen bonding is observed in the crystal.

Figure 1
Perspective view of the structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Synthesis and crystallization

To a solution of 1-(hex-1-yn-1-yloxy)-3-methylbenzene (94 mg, 0.5 mmol) in 2.0 ml of tetrahydrofuran (THF) was added neat 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin) (71 mg, 0.55 mmol) under nitrogen atmosphere. After stirring at room temperature for 1.5 h, the reaction mixture was concentrated and purified by on silica gel (petroleum ether/EtOAc = 60/1).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C₁₉H₂₉BO₃
M_r	316.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.0293 (9), 18.1230 (17), 10.7973 (10)
β (°)	97.475 (6)
V (Å³)	1945.9 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 )
T_min, T_max	0.983, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	30133, 4375, 2665
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.168, 1.09
No. of reflections	4375
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18
Computer programs: APEX2 and SAINT (Bruker, 2006 ), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1473545

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314616006118/xu4004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616006118/xu4004Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616006118/xu4004Isup3.mol

checkcif. DOI: 10.1107/S2414314616006118/xu4004sup4.pdf

Supporting information file. DOI: 10.1107/S2414314616006118/xu4004Isup5.cml

checkCIF report

Comment top

The title compound was previously prepared by Cui et al. (2013), and its derivatives were synthesized by Yang & Cheng (2001) and Whelligan et al. (2010). We present here the crystal structure of the compound. In teh molecule, the conformation of the dioxaborolane ring is similar to half chair, and the butyl group adopts an extended conformation with the C10–C11–C12–C13 torsion angle = 179.52 (19)°. No hydrogen bonding is observed in the crystal.

Experimental top

Structure description top

The title compound was previously prepared by Cui et al. (2013), and its derivatives were synthesized by Yang & Cheng (2001) and Whelligan et al. (2010). We present here the crystal structure of the compound (Fig. 1). In the molecule, the conformation of the dioxaborolane ring is similar to half chair, and the butyl group adopts an extended conformation with a C10—C11—C12—C13 torsion angle = 179.52 (19)°. No hydrogen bonding is observed in the crystal.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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. Perspective view of the structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

4,4,5,5-Tetramethyl-2-[(Z)-1-(3-methylphenoxy)hex-1-en-2-yl]-1,3,2-dioxaborolane top

Crystal data top

C₁₉H₂₉BO₃	F(000) = 688
M_r = 316.23	D_x = 1.079 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0293 (9) Å	Cell parameters from 4375 reflections
b = 18.1230 (17) Å	θ = 2.1–27.4°
c = 10.7973 (10) Å	µ = 0.07 mm⁻¹
β = 97.475 (6)°	T = 296 K
V = 1945.9 (3) Å³	Block, colourless
Z = 4	0.3 × 0.2 × 0.1 mm

Data collection top

Bruker APEXII diffractometer	4375 independent reflections
Radiation source: fine-focus sealed tube	2665 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 27.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
T_min = 0.983, T_max = 0.993	k = −23→21
30133 measured reflections	l = −13→13

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0826P)² + 0.1148P] where P = (F_o² + 2F_c²)/3
4375 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₉H₂₉BO₃	V = 1945.9 (3) Å³
M_r = 316.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0293 (9) Å	µ = 0.07 mm⁻¹
b = 18.1230 (17) Å	T = 296 K
c = 10.7973 (10) Å	0.3 × 0.2 × 0.1 mm
β = 97.475 (6)°

Data collection top

Bruker APEXII diffractometer	4375 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2665 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.993	R_int = 0.044
30133 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.09	Δρ_max = 0.18 e Å⁻³
4375 reflections	Δρ_min = −0.18 e Å⁻³
208 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 > 2sigma(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
B1	0.66602 (17)	0.11935 (10)	0.19395 (16)	0.0479 (4)
O1	0.49825 (11)	0.27876 (7)	0.01441 (12)	0.0662 (4)
O2	0.56737 (11)	0.06699 (6)	0.18524 (11)	0.0620 (4)
O3	0.78374 (10)	0.09596 (6)	0.25964 (11)	0.0573 (3)
C1	0.36387 (17)	0.29473 (9)	−0.02574 (16)	0.0558 (4)
C2	0.33922 (18)	0.33782 (9)	−0.13101 (16)	0.0587 (4)
H2A	0.4104	0.3531	−0.1721	0.070*
C3	0.2087 (2)	0.35875 (10)	−0.17633 (18)	0.0664 (5)
C4	0.1053 (2)	0.33435 (12)	−0.1136 (2)	0.0820 (7)
H4A	0.0170	0.3466	−0.1438	0.098*
C5	0.1308 (2)	0.29256 (12)	−0.0081 (3)	0.0882 (7)
H5A	0.0597	0.2772	0.0331	0.106*
C6	0.26130 (19)	0.27263 (11)	0.0386 (2)	0.0732 (5)
H6A	0.2789	0.2450	0.1115	0.088*
C7	0.1814 (3)	0.40687 (14)	−0.2895 (2)	0.1007 (8)
H7C	0.0864	0.4152	−0.3082	0.121*
H7B	0.2137	0.3830	−0.3592	0.121*
H7A	0.2266	0.4533	−0.2738	0.121*
C8	0.52791 (17)	0.21201 (9)	0.07200 (15)	0.0548 (4)
H8A	0.4622	0.1755	0.0649	0.066*
C9	0.64616 (15)	0.19761 (9)	0.13719 (14)	0.0493 (4)
C10	0.75572 (16)	0.25522 (10)	0.15952 (15)	0.0563 (4)
H10B	0.8418	0.2317	0.1547	0.068*
H10A	0.7419	0.2917	0.0933	0.068*
C11	0.76153 (18)	0.29400 (10)	0.28296 (16)	0.0632 (5)
H11B	0.7786	0.2579	0.3494	0.076*
H11A	0.6747	0.3163	0.2891	0.076*
C12	0.8690 (2)	0.35332 (11)	0.30207 (18)	0.0763 (6)
H12B	0.9557	0.3308	0.2964	0.092*
H12A	0.8523	0.3890	0.2349	0.092*
C13	0.8758 (3)	0.39323 (13)	0.4244 (2)	0.1006 (8)
H13C	0.9454	0.4299	0.4295	0.121*
H13B	0.8954	0.3587	0.4917	0.121*
H13A	0.7911	0.4167	0.4304	0.121*
C14	0.62832 (19)	−0.00170 (9)	0.23442 (18)	0.0635 (5)
C15	0.75651 (16)	0.02563 (10)	0.31787 (16)	0.0565 (4)
C16	0.6612 (3)	−0.04561 (13)	0.1223 (2)	0.1110 (9)
H16C	0.5792	−0.0618	0.0741	0.133*
H16B	0.7147	−0.0877	0.1505	0.133*
H16A	0.7103	−0.0150	0.0715	0.133*
C17	0.5277 (2)	−0.04152 (15)	0.3024 (3)	0.1157 (10)
H17C	0.4526	−0.0567	0.2436	0.139*
H17B	0.4971	−0.0091	0.3630	0.139*
H17A	0.5694	−0.0841	0.3438	0.139*
C18	0.8788 (2)	−0.02308 (12)	0.3206 (2)	0.0831 (6)
H18C	0.8927	−0.0352	0.2367	0.100*
H18B	0.8653	−0.0675	0.3656	0.100*
H18A	0.9562	0.0025	0.3612	0.100*
C19	0.7334 (3)	0.04403 (14)	0.45048 (18)	0.0917 (7)
H19C	0.6552	0.0747	0.4487	0.110*
H19B	0.8103	0.0697	0.4918	0.110*
H19A	0.7201	−0.0007	0.4948	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0444 (10)	0.0490 (10)	0.0490 (9)	−0.0016 (8)	0.0007 (8)	−0.0027 (8)
O1	0.0523 (7)	0.0530 (7)	0.0881 (9)	−0.0010 (5)	−0.0104 (6)	0.0185 (6)
O2	0.0509 (7)	0.0507 (7)	0.0791 (8)	−0.0044 (5)	−0.0114 (6)	0.0111 (6)
O3	0.0468 (6)	0.0527 (7)	0.0689 (7)	−0.0018 (5)	−0.0065 (5)	0.0086 (6)
C1	0.0504 (10)	0.0473 (9)	0.0661 (10)	0.0005 (7)	−0.0056 (8)	−0.0005 (8)
C2	0.0585 (11)	0.0536 (10)	0.0615 (10)	0.0058 (8)	−0.0012 (8)	0.0016 (8)
C3	0.0666 (12)	0.0567 (11)	0.0705 (11)	0.0123 (9)	−0.0117 (9)	−0.0080 (9)
C4	0.0536 (12)	0.0669 (13)	0.1195 (18)	0.0088 (10)	−0.0116 (12)	−0.0070 (13)
C5	0.0605 (13)	0.0714 (14)	0.136 (2)	0.0021 (11)	0.0232 (12)	0.0120 (14)
C6	0.0678 (12)	0.0633 (12)	0.0886 (14)	0.0002 (10)	0.0104 (10)	0.0164 (10)
C7	0.1099 (18)	0.0981 (18)	0.0862 (15)	0.0364 (15)	−0.0170 (13)	0.0121 (13)
C8	0.0571 (10)	0.0424 (9)	0.0620 (10)	−0.0049 (7)	−0.0037 (8)	0.0053 (7)
C9	0.0471 (9)	0.0484 (9)	0.0506 (9)	−0.0010 (7)	−0.0004 (7)	0.0011 (7)
C10	0.0530 (10)	0.0553 (10)	0.0593 (10)	−0.0056 (8)	0.0020 (7)	0.0041 (8)
C11	0.0690 (12)	0.0538 (10)	0.0662 (11)	−0.0074 (8)	0.0065 (9)	−0.0014 (8)
C12	0.0868 (14)	0.0681 (13)	0.0716 (12)	−0.0258 (11)	0.0013 (10)	−0.0003 (10)
C13	0.136 (2)	0.0864 (16)	0.0765 (14)	−0.0390 (15)	0.0029 (14)	−0.0076 (12)
C14	0.0657 (11)	0.0445 (9)	0.0749 (12)	−0.0028 (8)	−0.0108 (9)	0.0092 (8)
C15	0.0546 (10)	0.0541 (10)	0.0586 (9)	0.0042 (8)	−0.0011 (7)	0.0093 (8)
C16	0.160 (2)	0.0626 (14)	0.0960 (17)	0.0129 (15)	−0.0365 (16)	−0.0184 (12)
C17	0.0818 (16)	0.0952 (18)	0.164 (3)	−0.0247 (14)	−0.0082 (16)	0.0607 (18)
C18	0.0690 (13)	0.0736 (14)	0.1030 (16)	0.0160 (11)	−0.0028 (11)	0.0132 (12)
C19	0.1162 (18)	0.0980 (17)	0.0586 (12)	0.0114 (14)	0.0023 (11)	0.0079 (11)

Geometric parameters (Å, º) top

B1—O3	1.363 (2)	C11—C12	1.517 (2)
B1—O2	1.365 (2)	C11—H11B	0.9700
B1—C9	1.548 (2)	C11—H11A	0.9700
O1—C8	1.3749 (19)	C12—C13	1.500 (3)
O1—C1	1.3914 (19)	C12—H12B	0.9700
O2—C14	1.456 (2)	C12—H12A	0.9700
O3—C15	1.463 (2)	C13—H13C	0.9600
C1—C6	1.374 (3)	C13—H13B	0.9600
C1—C2	1.375 (2)	C13—H13A	0.9600
C2—C3	1.390 (2)	C14—C17	1.506 (3)
C2—H2A	0.9300	C14—C16	1.520 (3)
C3—C4	1.383 (3)	C14—C15	1.552 (2)
C3—C7	1.498 (3)	C15—C18	1.508 (2)
C4—C5	1.364 (3)	C15—C19	1.517 (3)
C4—H4A	0.9300	C16—H16C	0.9600
C5—C6	1.388 (3)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16A	0.9600
C6—H6A	0.9300	C17—H17C	0.9600
C7—H7C	0.9600	C17—H17B	0.9600
C7—H7B	0.9600	C17—H17A	0.9600
C7—H7A	0.9600	C18—H18C	0.9600
C8—C9	1.324 (2)	C18—H18B	0.9600
C8—H8A	0.9300	C18—H18A	0.9600
C9—C10	1.512 (2)	C19—H19C	0.9600
C10—C11	1.501 (2)	C19—H19B	0.9600
C10—H10B	0.9700	C19—H19A	0.9600
C10—H10A	0.9700

O3—B1—O2	112.99 (15)	C13—C12—C11	114.32 (18)
O3—B1—C9	123.30 (15)	C13—C12—H12B	108.7
O2—B1—C9	123.70 (14)	C11—C12—H12B	108.7
C8—O1—C1	117.89 (13)	C13—C12—H12A	108.7
B1—O2—C14	107.64 (12)	C11—C12—H12A	108.7
B1—O3—C15	107.28 (12)	H12B—C12—H12A	107.6
C6—C1—C2	121.19 (17)	C12—C13—H13C	109.5
C6—C1—O1	122.72 (16)	C12—C13—H13B	109.5
C2—C1—O1	116.00 (15)	H13C—C13—H13B	109.5
C1—C2—C3	120.40 (18)	C12—C13—H13A	109.5
C1—C2—H2A	119.8	H13C—C13—H13A	109.5
C3—C2—H2A	119.8	H13B—C13—H13A	109.5
C4—C3—C2	118.19 (18)	O2—C14—C17	108.13 (16)
C4—C3—C7	121.14 (19)	O2—C14—C16	106.33 (15)
C2—C3—C7	120.7 (2)	C17—C14—C16	111.4 (2)
C5—C4—C3	121.04 (19)	O2—C14—C15	102.45 (13)
C5—C4—H4A	119.5	C17—C14—C15	115.27 (17)
C3—C4—H4A	119.5	C16—C14—C15	112.36 (18)
C4—C5—C6	120.9 (2)	O3—C15—C18	108.75 (14)
C4—C5—H5A	119.6	O3—C15—C19	105.91 (15)
C6—C5—H5A	119.6	C18—C15—C19	109.50 (16)
C1—C6—C5	118.26 (19)	O3—C15—C14	102.45 (12)
C1—C6—H6A	120.9	C18—C15—C14	115.77 (16)
C5—C6—H6A	120.9	C19—C15—C14	113.67 (16)
C3—C7—H7C	109.5	C14—C16—H16C	109.5
C3—C7—H7B	109.5	C14—C16—H16B	109.5
H7C—C7—H7B	109.5	H16C—C16—H16B	109.5
C3—C7—H7A	109.5	C14—C16—H16A	109.5
H7C—C7—H7A	109.5	H16C—C16—H16A	109.5
H7B—C7—H7A	109.5	H16B—C16—H16A	109.5
C9—C8—O1	122.69 (15)	C14—C17—H17C	109.5
C9—C8—H8A	118.7	C14—C17—H17B	109.5
O1—C8—H8A	118.7	H17C—C17—H17B	109.5
C8—C9—C10	122.06 (15)	C14—C17—H17A	109.5
C8—C9—B1	116.84 (14)	H17C—C17—H17A	109.5
C10—C9—B1	121.07 (13)	H17B—C17—H17A	109.5
C11—C10—C9	114.10 (14)	C15—C18—H18C	109.5
C11—C10—H10B	108.7	C15—C18—H18B	109.5
C9—C10—H10B	108.7	H18C—C18—H18B	109.5
C11—C10—H10A	108.7	C15—C18—H18A	109.5
C9—C10—H10A	108.7	H18C—C18—H18A	109.5
H10B—C10—H10A	107.6	H18B—C18—H18A	109.5
C10—C11—C12	113.41 (15)	C15—C19—H19C	109.5
C10—C11—H11B	108.9	C15—C19—H19B	109.5
C12—C11—H11B	108.9	H19C—C19—H19B	109.5
C10—C11—H11A	108.9	C15—C19—H19A	109.5
C12—C11—H11A	108.9	H19C—C19—H19A	109.5
H11B—C11—H11A	107.7	H19B—C19—H19A	109.5

O3—B1—O2—C14	−8.47 (19)	O3—B1—C9—C10	−4.3 (2)
C9—B1—O2—C14	172.46 (15)	O2—B1—C9—C10	174.71 (15)
O2—B1—O3—C15	−9.78 (18)	C8—C9—C10—C11	96.8 (2)
C9—B1—O3—C15	169.30 (15)	B1—C9—C10—C11	−81.07 (19)
C8—O1—C1—C6	35.4 (2)	C9—C10—C11—C12	−178.12 (16)
C8—O1—C1—C2	−148.01 (16)	C10—C11—C12—C13	179.52 (19)
C6—C1—C2—C3	−1.4 (3)	B1—O2—C14—C17	143.74 (18)
O1—C1—C2—C3	−178.00 (15)	B1—O2—C14—C16	−96.49 (19)
C1—C2—C3—C4	−0.7 (3)	B1—O2—C14—C15	21.59 (17)
C1—C2—C3—C7	178.83 (18)	B1—O3—C15—C18	145.33 (15)
C2—C3—C4—C5	1.8 (3)	B1—O3—C15—C19	−97.07 (16)
C7—C3—C4—C5	−177.8 (2)	B1—O3—C15—C14	22.30 (17)
C3—C4—C5—C6	−0.7 (3)	O2—C14—C15—O3	−26.26 (17)
C2—C1—C6—C5	2.4 (3)	C17—C14—C15—O3	−143.43 (17)
O1—C1—C6—C5	178.81 (18)	C16—C14—C15—O3	87.46 (18)
C4—C5—C6—C1	−1.4 (3)	O2—C14—C15—C18	−144.43 (16)
C1—O1—C8—C9	−164.95 (16)	C17—C14—C15—C18	98.4 (2)
O1—C8—C9—C10	3.5 (3)	C16—C14—C15—C18	−30.7 (2)
O1—C8—C9—B1	−178.53 (15)	O2—C14—C15—C19	87.53 (18)
O3—B1—C9—C8	177.75 (15)	C17—C14—C15—C19	−29.6 (2)
O2—B1—C9—C8	−3.3 (2)	C16—C14—C15—C19	−158.76 (18)

Experimental details

Crystal data
Chemical formula	C₁₉H₂₉BO₃
M_r	316.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.0293 (9), 18.1230 (17), 10.7973 (10)
β (°)	97.475 (6)
V (Å³)	1945.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.983, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	30133, 4375, 2665
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.168, 1.09
No. of reflections	4375
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The work was supported by the chemical weight of the open fund (No. ZC323015033).

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cui, W.-J., Mao, M.-Y., He, Z.-Y. & Zhu, G.-G. (2013). J. Org. Chem. 78, 9815–9821. CrossRef CAS PubMed Google Scholar
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Whelligan, D. K., Thomson, D. W., Taylor, D. & Hoelder, S. (2010). J. Org. Chem. 75, 11–15. CrossRef PubMed CAS Google Scholar
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