3-(10-Chloro-9-anthr­yl)-5-[3-(prop-2-yn­yloxy)phenoxy­meth­yl]isoxazole

Li, J.; Xi, H.; Zhang, J.

doi:10.1107/S1600536809019229

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1401

doi:10.1107/S1600536809019229

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3-(10-Chloro-9-anthryl)-5-[3-(prop-2-ynyloxy)phenoxymethyl]isoxazole

Juan Li,^a Hailing Xi ^b and Jianming Zhang ^a ^*

^aKey Laboratory of Pesticide and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China, and ^b6th Department, Research Institute of Chemical Defence, Beijing 102205, People's Republic of China
^*Correspondence e-mail: bluemzj@163.com

(Received 23 April 2009; accepted 21 May 2009; online 29 May 2009)

In the title molecule, C₂₇H₁₈ClNO₃, the anthracene mean plane forms dihedral angles of 67.43 (2) and 15.75 (3)° with the isoxazole and benzene rings, respectively. In the crystal structure, C—H⋯π interactions link molecules into centrosymmetric dimers, which are further linked by weak intermolecular C—H⋯N hydrogen bonds into ribbons propagating in the [110] direction.

Related literature

For the preparation of the title compound, see Han et al. (2003 ). For pharmaceutical applications of isoxazole and its derivatives, see: De Luca et al. (2001 ); Yamamoto et al. (2007 ); Reuman et al. (2008 ).

Experimental

Crystal data

C₂₇H₁₈ClNO₃
M_r = 439.87
Triclinic, $[P \overline 1]$
a = 8.4816 (3) Å
b = 8.6450 (3) Å
c = 16.8606 (6) Å
α = 100.364 (1)°
β = 103.596 (1)°
γ = 94.965 (1)°
V = 1171.25 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 292 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: none
4812 measured reflections
4812 independent reflections
4227 reflections with I > 2σ(I)
R_int = 0.0000

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.163
S = 1.06
4812 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C19–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27⋯N1ⁱ	0.93	2.57	3.465 (3)	163
C16—H16⋯Cgⁱⁱ	0.93	2.67	3.431 (2)	140
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y, -z+1.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019229/cv2557sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019229/cv2557Isup2.hkl

checkCIF report

Comment top

Isoxazole and isoxazole derivatives are important pharmaceutical agents (De Luca et al., 2001), so they are widely investigated (Yamamoto et al., 2007; Reuman et al., 2008). As a part of our investigation into isoxazole derivatives, we report here the structure of the title compound (I).

In (I) (Fig. 1), the anthracene mean plane forms the dihedral angles of 67.43 (2)° and 15.75 (3)° with the isoxazole and benzene rings, respectively. In the crystal, C—H···π interactions (Table 1) link the molecules into centrosymmetric dimers, which are further linked by the weak intermolecular C—H···N hydrogen bonds (Table 1) into ribbons propagated in direction [110]. The porous crystal packing contains voids of 171 Å³.

Related literature top

For the preparation of the title compound, see Han et al. (2003). For general background, see: De Luca et al. (2001); Yamamoto et al. (2007); Reuman et al. (2008).

Experimental top

The title compound was synthesized according to the procedure of Han et al. (2003) in 32% isolated yield. Crystals of (I) suitable for X-ray data collection were obtained by slow evaporation of a methaoland DMF solution in ratio of 50:1 at 298 K.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by spheres of arbitrary radius.

3-(10-Chloro-9-anthryl)-5-[3-(prop-2-ynyloxy)phenoxymethyl]isoxazole top

Crystal data top

C₂₇H₁₈ClNO₃	Z = 2
M_r = 439.87	F(000) = 456
Triclinic, P1	D_x = 1.247 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4816 (3) Å	Cell parameters from 6384 reflections
b = 8.6450 (3) Å	θ = 2.5–28.2°
c = 16.8606 (6) Å	µ = 0.19 mm⁻¹
α = 100.364 (1)°	T = 292 K
β = 103.596 (1)°	Block, colourless
γ = 94.965 (1)°	0.30 × 0.20 × 0.10 mm
V = 1171.25 (7) Å³

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4227 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 26.5°, θ_min = 2.4°
ϕ and ω scans	h = −10→10
4812 measured reflections	k = −10→10
4812 independent reflections	l = 0→21

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0786P)² + 0.2928P] where P = (F_o² + 2F_c²)/3
4812 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₇H₁₈ClNO₃	γ = 94.965 (1)°
M_r = 439.87	V = 1171.25 (7) Å³
Triclinic, P1	Z = 2
a = 8.4816 (3) Å	Mo Kα radiation
b = 8.6450 (3) Å	µ = 0.19 mm⁻¹
c = 16.8606 (6) Å	T = 292 K
α = 100.364 (1)°	0.30 × 0.20 × 0.10 mm
β = 103.596 (1)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4227 reflections with I > 2σ(I)
4812 measured reflections	R_int = 0.000
4812 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.06	Δρ_max = 0.32 e Å⁻³
4812 reflections	Δρ_min = −0.39 e Å⁻³
289 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	0.2863 (2)	0.3620 (2)	0.91382 (11)	0.0372 (4)
C2	0.1335 (3)	0.4195 (2)	0.91474 (14)	0.0487 (5)
H2	0.0916	0.4184	0.9609	0.058*
C3	0.0490 (3)	0.4751 (3)	0.85017 (16)	0.0566 (5)
H3	−0.0495	0.5128	0.8526	0.068*
C4	0.1087 (3)	0.4767 (3)	0.77859 (15)	0.0534 (5)
H4	0.0487	0.5145	0.7341	0.064*
C5	0.2529 (2)	0.4234 (2)	0.77469 (12)	0.0426 (4)
H5	0.2899	0.4244	0.7270	0.051*
C6	0.3493 (2)	0.36581 (19)	0.84180 (10)	0.0338 (4)
C7	0.4989 (2)	0.30988 (19)	0.83910 (10)	0.0318 (3)
C8	0.5881 (2)	0.2499 (2)	0.90563 (10)	0.0335 (4)
C9	0.7423 (2)	0.1965 (2)	0.90562 (12)	0.0430 (4)
H9	0.7856	0.2003	0.8601	0.052*
C10	0.8275 (3)	0.1400 (3)	0.97066 (14)	0.0543 (5)
H10	0.9282	0.1063	0.9693	0.065*
C11	0.7643 (3)	0.1322 (3)	1.04012 (13)	0.0580 (6)
H11	0.8229	0.0920	1.0840	0.070*
C12	0.6195 (3)	0.1825 (3)	1.04358 (11)	0.0504 (5)
H12	0.5801	0.1767	1.0901	0.060*
C13	0.5254 (2)	0.2444 (2)	0.97749 (10)	0.0369 (4)
C14	0.3769 (2)	0.3003 (2)	0.97840 (11)	0.0393 (4)
C15	0.56449 (19)	0.3098 (2)	0.76469 (10)	0.0313 (3)
C16	0.5831 (2)	0.1769 (2)	0.70657 (11)	0.0372 (4)
H16	0.5563	0.0702	0.7063	0.045*
C17	0.6479 (2)	0.2387 (2)	0.65203 (10)	0.0369 (4)
C18	0.7037 (2)	0.1683 (3)	0.57805 (11)	0.0447 (4)
H18A	0.8181	0.2071	0.5854	0.054*
H18B	0.6918	0.0536	0.5705	0.054*
C19	0.6541 (2)	0.1848 (2)	0.43448 (11)	0.0379 (4)
C20	0.7742 (2)	0.0930 (2)	0.42197 (11)	0.0378 (4)
H20	0.8285	0.0457	0.4640	0.045*
C21	0.8133 (2)	0.0720 (2)	0.34504 (11)	0.0356 (4)
C22	0.7331 (2)	0.1422 (2)	0.28241 (12)	0.0428 (4)
H22	0.7601	0.1289	0.2315	0.051*
C23	0.6120 (2)	0.2329 (2)	0.29685 (12)	0.0444 (4)
H23	0.5571	0.2799	0.2549	0.053*
C24	0.5710 (2)	0.2549 (2)	0.37219 (12)	0.0429 (4)
H24	0.4891	0.3156	0.3810	0.051*
C25	0.9797 (3)	−0.0505 (2)	0.26169 (12)	0.0444 (4)
H25A	0.8811	−0.0784	0.2163	0.053*
H25B	1.0408	−0.1403	0.2597	0.053*
C26	1.0785 (2)	0.0859 (2)	0.24940 (12)	0.0447 (4)
C27	1.1606 (3)	0.1948 (3)	0.24028 (15)	0.0581 (6)
H27	1.2255	0.2809	0.2331	0.070*
Cl1	0.29951 (8)	0.29325 (7)	1.06495 (3)	0.0617 (2)
N1	0.6140 (2)	0.44298 (18)	0.74604 (9)	0.0423 (4)
O1	0.66859 (17)	0.39855 (16)	0.67356 (8)	0.0448 (3)
O2	0.60568 (17)	0.2133 (2)	0.50758 (8)	0.0520 (4)
O3	0.93481 (17)	−0.02142 (17)	0.33887 (8)	0.0473 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0398 (9)	0.0328 (8)	0.0409 (9)	0.0008 (7)	0.0202 (7)	0.0011 (7)
C2	0.0488 (11)	0.0461 (11)	0.0581 (12)	0.0079 (8)	0.0309 (9)	0.0046 (9)
C3	0.0447 (11)	0.0537 (12)	0.0799 (15)	0.0180 (9)	0.0302 (11)	0.0117 (11)
C4	0.0455 (11)	0.0538 (12)	0.0653 (13)	0.0155 (9)	0.0136 (10)	0.0202 (10)
C5	0.0425 (10)	0.0460 (10)	0.0436 (10)	0.0086 (8)	0.0149 (8)	0.0140 (8)
C6	0.0373 (8)	0.0313 (8)	0.0342 (8)	0.0027 (6)	0.0143 (7)	0.0045 (6)
C7	0.0358 (8)	0.0333 (8)	0.0279 (8)	0.0031 (6)	0.0137 (6)	0.0039 (6)
C8	0.0394 (8)	0.0344 (8)	0.0279 (8)	0.0032 (7)	0.0118 (7)	0.0060 (6)
C9	0.0427 (10)	0.0528 (11)	0.0389 (9)	0.0120 (8)	0.0144 (8)	0.0155 (8)
C10	0.0475 (11)	0.0664 (13)	0.0528 (12)	0.0179 (10)	0.0087 (9)	0.0231 (10)
C11	0.0634 (13)	0.0702 (14)	0.0412 (11)	0.0117 (11)	0.0027 (10)	0.0265 (10)
C12	0.0624 (13)	0.0605 (12)	0.0280 (9)	0.0016 (10)	0.0099 (8)	0.0139 (8)
C13	0.0448 (9)	0.0374 (9)	0.0270 (8)	−0.0022 (7)	0.0111 (7)	0.0044 (6)
C14	0.0503 (10)	0.0390 (9)	0.0302 (8)	−0.0030 (7)	0.0218 (7)	0.0007 (7)
C15	0.0296 (7)	0.0390 (9)	0.0278 (8)	0.0065 (6)	0.0101 (6)	0.0093 (6)
C16	0.0433 (9)	0.0375 (9)	0.0343 (9)	0.0070 (7)	0.0165 (7)	0.0070 (7)
C17	0.0393 (9)	0.0444 (10)	0.0300 (8)	0.0106 (7)	0.0117 (7)	0.0089 (7)
C18	0.0493 (10)	0.0601 (12)	0.0309 (9)	0.0190 (9)	0.0174 (8)	0.0106 (8)
C19	0.0392 (9)	0.0472 (10)	0.0286 (8)	0.0072 (7)	0.0124 (7)	0.0051 (7)
C20	0.0406 (9)	0.0464 (10)	0.0302 (8)	0.0099 (7)	0.0109 (7)	0.0131 (7)
C21	0.0376 (9)	0.0397 (9)	0.0333 (8)	0.0067 (7)	0.0143 (7)	0.0097 (7)
C22	0.0448 (10)	0.0568 (11)	0.0339 (9)	0.0111 (8)	0.0163 (7)	0.0175 (8)
C23	0.0453 (10)	0.0555 (11)	0.0389 (9)	0.0154 (8)	0.0110 (8)	0.0217 (8)
C24	0.0405 (9)	0.0523 (11)	0.0391 (9)	0.0161 (8)	0.0117 (8)	0.0110 (8)
C25	0.0513 (10)	0.0448 (10)	0.0430 (10)	0.0123 (8)	0.0252 (8)	0.0039 (8)
C26	0.0413 (9)	0.0553 (11)	0.0408 (10)	0.0135 (8)	0.0154 (8)	0.0089 (8)
C27	0.0500 (11)	0.0662 (14)	0.0636 (14)	0.0066 (10)	0.0203 (10)	0.0206 (11)
Cl1	0.0751 (4)	0.0780 (4)	0.0412 (3)	0.0068 (3)	0.0364 (3)	0.0093 (2)
N1	0.0581 (9)	0.0403 (8)	0.0368 (8)	0.0081 (7)	0.0263 (7)	0.0101 (6)
O1	0.0603 (8)	0.0456 (7)	0.0381 (7)	0.0079 (6)	0.0277 (6)	0.0131 (5)
O2	0.0505 (8)	0.0849 (10)	0.0285 (6)	0.0301 (7)	0.0174 (6)	0.0122 (6)
O3	0.0562 (8)	0.0576 (8)	0.0425 (7)	0.0274 (6)	0.0266 (6)	0.0192 (6)

Geometric parameters (Å, º) top

C1—C14	1.395 (3)	C15—C16	1.416 (2)
C1—C2	1.430 (3)	C16—C17	1.340 (2)
C1—C6	1.441 (2)	C16—H16	0.9300
C2—C3	1.345 (3)	C17—O1	1.349 (2)
C2—H2	0.9300	C17—C18	1.485 (2)
C3—C4	1.416 (3)	C18—O2	1.418 (2)
C3—H3	0.9300	C18—H18A	0.9700
C4—C5	1.355 (3)	C18—H18B	0.9700
C4—H4	0.9300	C19—C20	1.376 (3)
C5—C6	1.427 (2)	C19—O2	1.377 (2)
C5—H5	0.9300	C19—C24	1.386 (3)
C6—C7	1.404 (2)	C20—C21	1.398 (2)
C7—C8	1.406 (2)	C20—H20	0.9300
C7—C15	1.487 (2)	C21—O3	1.374 (2)
C8—C9	1.424 (3)	C21—C22	1.382 (2)
C8—C13	1.440 (2)	C22—C23	1.385 (3)
C9—C10	1.358 (3)	C22—H22	0.9300
C9—H9	0.9300	C23—C24	1.379 (3)
C10—C11	1.407 (3)	C23—H23	0.9300
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.348 (3)	C25—O3	1.426 (2)
C11—H11	0.9300	C25—C26	1.461 (3)
C12—C13	1.427 (3)	C25—H25A	0.9700
C12—H12	0.9300	C25—H25B	0.9700
C13—C14	1.390 (3)	C26—C27	1.176 (3)
C14—Cl1	1.7434 (17)	C27—H27	0.9300
C15—N1	1.308 (2)	N1—O1	1.4082 (19)

C14—C1—C2	123.58 (17)	C16—C15—C7	127.76 (15)
C14—C1—C6	118.09 (16)	C17—C16—C15	104.87 (16)
C2—C1—C6	118.33 (17)	C17—C16—H16	127.6
C3—C2—C1	121.36 (19)	C15—C16—H16	127.6
C3—C2—H2	119.3	C16—C17—O1	109.76 (16)
C1—C2—H2	119.3	C16—C17—C18	133.60 (18)
C2—C3—C4	120.68 (19)	O1—C17—C18	116.60 (16)
C2—C3—H3	119.7	O2—C18—C17	107.63 (15)
C4—C3—H3	119.7	O2—C18—H18A	110.2
C5—C4—C3	120.19 (19)	C17—C18—H18A	110.2
C5—C4—H4	119.9	O2—C18—H18B	110.2
C3—C4—H4	119.9	C17—C18—H18B	110.2
C4—C5—C6	121.70 (18)	H18A—C18—H18B	108.5
C4—C5—H5	119.1	C20—C19—O2	123.81 (16)
C6—C5—H5	119.1	C20—C19—C24	121.26 (16)
C7—C6—C5	122.69 (16)	O2—C19—C24	114.93 (16)
C7—C6—C1	119.58 (15)	C19—C20—C21	118.90 (16)
C5—C6—C1	117.71 (16)	C19—C20—H20	120.6
C6—C7—C8	120.95 (15)	C21—C20—H20	120.6
C6—C7—C15	120.45 (14)	O3—C21—C22	124.87 (16)
C8—C7—C15	118.59 (15)	O3—C21—C20	114.38 (15)
C7—C8—C9	122.18 (15)	C22—C21—C20	120.76 (17)
C7—C8—C13	119.87 (16)	C21—C22—C23	118.85 (17)
C9—C8—C13	117.94 (15)	C21—C22—H22	120.6
C10—C9—C8	121.44 (18)	C23—C22—H22	120.6
C10—C9—H9	119.3	C24—C23—C22	121.41 (16)
C8—C9—H9	119.3	C24—C23—H23	119.3
C9—C10—C11	120.4 (2)	C22—C23—H23	119.3
C9—C10—H10	119.8	C23—C24—C19	118.82 (17)
C11—C10—H10	119.8	C23—C24—H24	120.6
C12—C11—C10	120.54 (18)	C19—C24—H24	120.6
C12—C11—H11	119.7	O3—C25—C26	112.99 (15)
C10—C11—H11	119.7	O3—C25—H25A	109.0
C11—C12—C13	121.53 (18)	C26—C25—H25A	109.0
C11—C12—H12	119.2	O3—C25—H25B	109.0
C13—C12—H12	119.2	C26—C25—H25B	109.0
C14—C13—C12	123.94 (17)	H25A—C25—H25B	107.8
C14—C13—C8	117.93 (16)	C27—C26—C25	178.8 (2)
C12—C13—C8	118.13 (18)	C26—C27—H27	180.0
C13—C14—C1	123.58 (16)	C15—N1—O1	105.45 (14)
C13—C14—Cl1	118.27 (14)	C17—O1—N1	108.51 (13)
C1—C14—Cl1	118.15 (15)	C19—O2—C18	117.55 (14)
N1—C15—C16	111.40 (15)	C21—O3—C25	117.66 (14)
N1—C15—C7	120.84 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···N1ⁱ	0.93	2.57	3.465 (3)	163
C16—H16···Cgⁱⁱ	0.93	2.67	3.431 (2)	140

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

Experimental details

Crystal data
Chemical formula	C₂₇H₁₈ClNO₃
M_r	439.87
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	8.4816 (3), 8.6450 (3), 16.8606 (6)
α, β, γ (°)	100.364 (1), 103.596 (1), 94.965 (1)
V (Å³)	1171.25 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4812, 4812, 4227
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.163, 1.06
No. of reflections	4812
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.39

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···N1ⁱ	0.93	2.57	3.465 (3)	162.8
C16—H16···Cgⁱⁱ	0.93	2.67	3.431 (2)	139.7

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

Acknowledgements

The authors thank Dr Xiang-Gao Meng for the X-ray data collection.

References

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