S-4-Chloro­phenyl 9,10-dihydro­acridine-9-carbothio­ate

Duan, Y.; Sun, H.; Guo, P.; Ji, M.

doi:10.1107/S1600536809003468

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o446

doi:10.1107/S1600536809003468

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S-4-Chlorophenyl 9,10-dihydroacridine-9-carbothioate

Yanbing Duan,^a Haifeng Sun,^a Peng Guo ^b and Min Ji ^a ^*

^aSchool of Chemistry and Chemical Engineering, Southeast University, 210096 Nanjing, People's Republic of China, and ^bChangchun Institute of Applied Chemistry, ChineseAcademy of Sciences, 130022 Changchun, People's Republic of China
^*Correspondence e-mail: dybwell@gmail.com

(Received 30 December 2008; accepted 28 January 2009; online 4 February 2009)

In tricyclic fragment of the title molecule, C₂₀H₁₄ClNOS, the central 1,4-dihydropyridine ring adopts a boat conformation while the two benzene rings form a dihedral angle of 17.38 (5)°. In the crystal structure, weak intermolecular N—H⋯O hydrogen bonds link the molecules into chains propagating along the b axis.

Related literature

For applications of acridine derivatives, see: Dodeigne et al. (2000 ); Ashmore et al. (2008 ); Zomer & Jacquemijns (2001 ).

Experimental

Crystal data

C₂₀H₁₄ClNOS
M_r = 351.83
Monoclinic, P 2₁ /n
a = 6.3171 (13) Å
b = 14.535 (3) Å
c = 18.169 (4) Å
β = 96.85 (3)°
V = 1656.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 293 (2) K
0.15 × 0.09 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.963, T_max = 0.971
16788 measured reflections
3788 independent reflections
2287 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.129
S = 1.04
3788 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.54	3.283 (3)	145
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2000 ); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003468/cv2506sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003468/cv2506Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was synthesized from S-4-chlorophenyl acridine-9-carbothioate catalyzed by zinc powder and glacial acetic acid using dichlormethane as solvent under the protection of nitrogen at room temperature. (I) is an important intermediate for the synthesis of acridine derivatives which are precursors of practically important chemiluminescent indicators and the chemiluminogenic fragments of chemiluminescent labels (Dodeigne et al., 2000; Ashmore et al., 2008; Zomer & Jacquemijns, 2001).

In (I) (Fig. 1), the 1,4-dihydropyridine ring (C1/C6/C7/C12/C13/N1) adopts a boat conformation: atoms C1, C6, C7 and C12 are coplanar, with atoms C13 and N1 derivating from the plane by 0.072 (9) and 0.300 (9) Å, respectively. The dihedral angle between the C1-C6 ring and C1/C6/C7/C12 plane is 11.43 (5)°. The dihedral angle between the C7-C12 plane and C1/C6/C7/C12 plane is 13.68 (5)°. In the crystal, weak intermolecular N—H···O hydrogen bonds (Table 1). link the molecules into chains propagated along b axis.

Related literature top

For applications of acridine derivatives, see: Dodeigne et al. (2000); Ashmore et al. (2008); Zomer & Jacquemijns (2001).

Experimental top

All chemicals used(reagent grade) were commercially available. S-4-chlorophenyl acridine-9-carbothioate 5.58 g (0.016 mol) was dissolved by dichlormethane, zinc powder 6 g (0.09 mol) and glacial acetic acid 2 mL were added and stirred under the protection of nitrogen at room temperature for 45 min. The mixture was filtered, and evaporated the dissolvent. Colorless crystal of the title compound suitable for X-ray analysis was obtained by recrystallization using dichlormethane. ¹HMNR(300 MHz, CDCl₃): 5.22(1H, s), 6.80(1H, s), 6.81(2H, d), 6.94–6.98(2H, t), 7.18(2H, t), 7.23(2H, dd), 7.27(2H, dd), 7.30(2H,d).

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalStructure (Rigaku/MSC, 2003); 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: SHELXL97 (Sheldrick, 2008).

Figures top

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

S-4-Chlorophenyl 9,10-dihydroacridine-9-carbothioate top

Crystal data top

C₂₀H₁₄ClNOS	F(000) = 728
M_r = 351.83	D_x = 1.411 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 12319 reflections
a = 6.3171 (13) Å	θ = 3.0–27.5°
b = 14.535 (3) Å	µ = 0.36 mm⁻¹
c = 18.169 (4) Å	T = 293 K
β = 96.85 (3)°	Block, colorless
V = 1656.4 (6) Å³	0.15 × 0.09 × 0.07 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3788 independent reflections
Radiation source: fine-focus sealed tube	2287 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.963, T_max = 0.971	k = −18→18
16788 measured reflections	l = −23→23

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) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0388P)² + 0.6284P] where P = (F_o² + 2F_c²)/3
3788 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₀H₁₄ClNOS	V = 1656.4 (6) Å³
M_r = 351.83	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.3171 (13) Å	µ = 0.36 mm⁻¹
b = 14.535 (3) Å	T = 293 K
c = 18.169 (4) Å	0.15 × 0.09 × 0.07 mm
β = 96.85 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	3788 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2287 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.971	R_int = 0.069
16788 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.04	Δρ_max = 0.21 e Å⁻³
3788 reflections	Δρ_min = −0.31 e Å⁻³
217 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
S1	0.79621 (14)	0.07317 (5)	0.13309 (4)	0.0622 (3)
Cl1	0.31742 (17)	−0.27324 (6)	−0.00643 (5)	0.0881 (3)
O1	0.9837 (3)	−0.05520 (12)	0.21991 (11)	0.0601 (6)
N1	0.7547 (4)	0.24449 (14)	0.27564 (13)	0.0506 (6)
H1A	0.6458	0.2804	0.2693	0.061*
C1	1.0780 (4)	0.19172 (17)	0.23159 (14)	0.0408 (6)
C2	1.2502 (5)	0.21117 (19)	0.19322 (16)	0.0527 (7)
H2A	1.3570	0.1674	0.1919	0.063*
C3	1.2669 (5)	0.2938 (2)	0.15705 (17)	0.0630 (9)
H3A	1.3837	0.3056	0.1318	0.076*
C4	1.1082 (5)	0.3588 (2)	0.15878 (17)	0.0597 (8)
H4A	1.1162	0.4141	0.1335	0.072*
C5	0.9387 (5)	0.34239 (18)	0.19761 (16)	0.0530 (7)
H5A	0.8337	0.3870	0.1990	0.064*
C6	0.9226 (4)	0.25965 (17)	0.23493 (15)	0.0419 (6)
C7	0.7560 (4)	0.17308 (17)	0.32648 (14)	0.0441 (6)
C8	0.6100 (5)	0.1711 (2)	0.37797 (16)	0.0584 (8)
H8A	0.5062	0.2166	0.3771	0.070*
C9	0.6178 (6)	0.1023 (2)	0.43034 (18)	0.0703 (9)
H9A	0.5190	0.1016	0.4644	0.084*
C10	0.7702 (6)	0.0346 (2)	0.43274 (17)	0.0660 (9)
H10A	0.7774	−0.0109	0.4689	0.079*
C11	0.9126 (5)	0.03501 (19)	0.38071 (16)	0.0534 (7)
H11A	1.0146	−0.0113	0.3818	0.064*
C12	0.9071 (4)	0.10270 (16)	0.32687 (14)	0.0412 (6)
C13	1.0523 (4)	0.09894 (16)	0.26639 (14)	0.0397 (6)
H13A	1.1931	0.0778	0.2884	0.048*
C14	0.9580 (4)	0.02581 (17)	0.21057 (14)	0.0392 (6)
C15	0.6677 (5)	−0.02802 (18)	0.09621 (15)	0.0472 (7)
C16	0.4798 (5)	−0.0559 (2)	0.12017 (17)	0.0616 (8)
H16A	0.4246	−0.0231	0.1575	0.074*
C17	0.3721 (5)	−0.1317 (2)	0.08959 (19)	0.0627 (8)
H17A	0.2452	−0.1505	0.1061	0.075*
C18	0.4549 (5)	−0.17925 (19)	0.03436 (16)	0.0525 (7)
C19	0.6430 (5)	−0.15349 (19)	0.01005 (16)	0.0590 (8)
H19A	0.6984	−0.1867	−0.0270	0.071*
C20	0.7491 (5)	−0.07752 (19)	0.04145 (16)	0.0545 (7)
H20A	0.8773	−0.0595	0.0254	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0851 (6)	0.0375 (4)	0.0563 (5)	−0.0065 (4)	−0.0236 (4)	−0.0005 (3)
Cl1	0.1100 (8)	0.0614 (5)	0.0877 (7)	−0.0439 (5)	−0.0092 (6)	−0.0036 (4)
O1	0.0727 (14)	0.0352 (10)	0.0672 (13)	0.0101 (9)	−0.0133 (11)	−0.0050 (9)
N1	0.0417 (13)	0.0450 (13)	0.0655 (16)	0.0110 (11)	0.0080 (12)	0.0063 (11)
C1	0.0369 (14)	0.0391 (14)	0.0446 (15)	−0.0052 (11)	−0.0031 (12)	−0.0110 (12)
C2	0.0458 (17)	0.0481 (16)	0.0647 (19)	−0.0078 (13)	0.0086 (14)	−0.0177 (14)
C3	0.065 (2)	0.060 (2)	0.067 (2)	−0.0258 (17)	0.0160 (17)	−0.0148 (16)
C4	0.071 (2)	0.0448 (16)	0.063 (2)	−0.0156 (16)	0.0051 (17)	−0.0029 (14)
C5	0.0556 (18)	0.0400 (15)	0.0613 (19)	−0.0007 (13)	−0.0022 (15)	−0.0024 (13)
C6	0.0426 (15)	0.0381 (14)	0.0433 (15)	−0.0049 (12)	−0.0021 (12)	−0.0067 (11)
C7	0.0476 (16)	0.0404 (14)	0.0436 (15)	0.0016 (12)	0.0026 (13)	−0.0078 (12)
C8	0.059 (2)	0.0567 (18)	0.062 (2)	0.0092 (15)	0.0154 (16)	−0.0090 (15)
C9	0.083 (2)	0.072 (2)	0.060 (2)	−0.002 (2)	0.0257 (18)	−0.0017 (18)
C10	0.086 (2)	0.0584 (19)	0.054 (2)	−0.0017 (18)	0.0119 (18)	0.0041 (15)
C11	0.0609 (19)	0.0470 (16)	0.0505 (17)	0.0069 (14)	−0.0002 (15)	−0.0012 (13)
C12	0.0428 (15)	0.0378 (13)	0.0415 (15)	−0.0010 (12)	−0.0014 (12)	−0.0070 (11)
C13	0.0329 (14)	0.0406 (14)	0.0443 (15)	0.0044 (11)	−0.0012 (11)	−0.0061 (11)
C14	0.0372 (14)	0.0370 (14)	0.0434 (15)	0.0003 (11)	0.0050 (11)	−0.0028 (11)
C15	0.0544 (18)	0.0388 (14)	0.0444 (16)	−0.0044 (13)	−0.0102 (13)	0.0012 (12)
C16	0.072 (2)	0.0538 (19)	0.060 (2)	−0.0016 (16)	0.0084 (17)	−0.0086 (15)
C17	0.0531 (19)	0.0609 (19)	0.076 (2)	−0.0119 (16)	0.0141 (17)	0.0053 (17)
C18	0.0607 (19)	0.0430 (15)	0.0500 (17)	−0.0166 (14)	−0.0097 (14)	0.0069 (13)
C19	0.078 (2)	0.0481 (17)	0.0500 (18)	−0.0111 (16)	0.0060 (16)	−0.0104 (14)
C20	0.0545 (19)	0.0500 (17)	0.0586 (18)	−0.0112 (14)	0.0055 (15)	−0.0007 (14)

Geometric parameters (Å, º) top

S1—C15	1.772 (3)	C8—H8A	0.9300
S1—C14	1.777 (3)	C9—C10	1.373 (4)
Cl1—C18	1.737 (3)	C9—H9A	0.9300
O1—C14	1.198 (3)	C10—C11	1.380 (4)
N1—C6	1.381 (3)	C10—H10A	0.9300
N1—C7	1.389 (3)	C11—C12	1.385 (4)
N1—H1A	0.8600	C11—H11A	0.9300
C1—C2	1.389 (4)	C12—C13	1.514 (4)
C1—C6	1.399 (4)	C13—C14	1.539 (3)
C1—C13	1.506 (3)	C13—H13A	0.9800
C2—C3	1.380 (4)	C15—C16	1.373 (4)
C2—H2A	0.9300	C15—C20	1.376 (4)
C3—C4	1.380 (4)	C16—C17	1.378 (4)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.371 (4)	C17—C18	1.372 (4)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.390 (4)	C18—C19	1.368 (4)
C5—H5A	0.9300	C19—C20	1.380 (4)
C7—C8	1.391 (4)	C19—H19A	0.9300
C7—C12	1.398 (3)	C20—H20A	0.9300
C8—C9	1.378 (4)

C15—S1—C14	99.92 (12)	C10—C11—C12	121.6 (3)
C6—N1—C7	122.1 (2)	C10—C11—H11A	119.2
C6—N1—H1A	119.0	C12—C11—H11A	119.2
C7—N1—H1A	119.0	C11—C12—C7	118.9 (3)
C2—C1—C6	118.3 (2)	C11—C12—C13	121.4 (2)
C2—C1—C13	121.5 (2)	C7—C12—C13	119.7 (2)
C6—C1—C13	120.2 (2)	C1—C13—C12	112.2 (2)
C3—C2—C1	121.7 (3)	C1—C13—C14	113.2 (2)
C3—C2—H2A	119.2	C12—C13—C14	106.4 (2)
C1—C2—H2A	119.2	C1—C13—H13A	108.3
C2—C3—C4	119.2 (3)	C12—C13—H13A	108.3
C2—C3—H3A	120.4	C14—C13—H13A	108.3
C4—C3—H3A	120.4	O1—C14—C13	123.4 (2)
C5—C4—C3	120.4 (3)	O1—C14—S1	123.3 (2)
C5—C4—H4A	119.8	C13—C14—S1	113.29 (17)
C3—C4—H4A	119.8	C16—C15—C20	119.1 (3)
C4—C5—C6	120.6 (3)	C16—C15—S1	119.9 (2)
C4—C5—H5A	119.7	C20—C15—S1	120.9 (2)
C6—C5—H5A	119.7	C15—C16—C17	120.8 (3)
N1—C6—C5	120.3 (2)	C15—C16—H16A	119.6
N1—C6—C1	119.9 (2)	C17—C16—H16A	119.6
C5—C6—C1	119.8 (3)	C18—C17—C16	119.0 (3)
N1—C7—C8	120.7 (2)	C18—C17—H17A	120.5
N1—C7—C12	120.0 (2)	C16—C17—H17A	120.5
C8—C7—C12	119.3 (3)	C19—C18—C17	121.3 (3)
C9—C8—C7	120.5 (3)	C19—C18—Cl1	119.1 (2)
C9—C8—H8A	119.8	C17—C18—Cl1	119.6 (2)
C7—C8—H8A	119.8	C18—C19—C20	118.9 (3)
C10—C9—C8	120.6 (3)	C18—C19—H19A	120.5
C10—C9—H9A	119.7	C20—C19—H19A	120.5
C8—C9—H9A	119.7	C15—C20—C19	120.8 (3)
C9—C10—C11	119.1 (3)	C15—C20—H20A	119.6
C9—C10—H10A	120.4	C19—C20—H20A	119.6
C11—C10—H10A	120.4

C6—C1—C2—C3	−2.0 (4)	C2—C1—C13—C12	159.2 (2)
C13—C1—C2—C3	175.6 (2)	C6—C1—C13—C12	−23.3 (3)
C1—C2—C3—C4	−0.2 (4)	C2—C1—C13—C14	−80.3 (3)
C2—C3—C4—C5	1.7 (4)	C6—C1—C13—C14	97.2 (3)
C3—C4—C5—C6	−0.9 (4)	C11—C12—C13—C1	−159.6 (2)
C7—N1—C6—C5	−165.4 (2)	C7—C12—C13—C1	23.8 (3)
C7—N1—C6—C1	14.2 (4)	C11—C12—C13—C14	76.1 (3)
C4—C5—C6—N1	178.2 (3)	C7—C12—C13—C14	−100.5 (3)
C4—C5—C6—C1	−1.4 (4)	C1—C13—C14—O1	156.3 (3)
C2—C1—C6—N1	−176.8 (2)	C12—C13—C14—O1	−80.0 (3)
C13—C1—C6—N1	5.6 (4)	C1—C13—C14—S1	−26.6 (3)
C2—C1—C6—C5	2.8 (4)	C12—C13—C14—S1	97.1 (2)
C13—C1—C6—C5	−174.8 (2)	C15—S1—C14—O1	11.1 (3)
C6—N1—C7—C8	165.7 (3)	C15—S1—C14—C13	−166.00 (19)
C6—N1—C7—C12	−13.5 (4)	C14—S1—C15—C16	89.1 (2)
N1—C7—C8—C9	−177.2 (3)	C14—S1—C15—C20	−93.6 (2)
C12—C7—C8—C9	2.0 (4)	C20—C15—C16—C17	−0.6 (4)
C7—C8—C9—C10	0.2 (5)	S1—C15—C16—C17	176.8 (2)
C8—C9—C10—C11	−1.7 (5)	C15—C16—C17—C18	−0.3 (5)
C9—C10—C11—C12	0.9 (5)	C16—C17—C18—C19	1.0 (5)
C10—C11—C12—C7	1.3 (4)	C16—C17—C18—Cl1	−178.3 (2)
C10—C11—C12—C13	−175.3 (3)	C17—C18—C19—C20	−0.8 (4)
N1—C7—C12—C11	176.5 (2)	Cl1—C18—C19—C20	178.5 (2)
C8—C7—C12—C11	−2.7 (4)	C16—C15—C20—C19	0.8 (4)
N1—C7—C12—C13	−6.9 (4)	S1—C15—C20—C19	−176.6 (2)
C8—C7—C12—C13	173.9 (2)	C18—C19—C20—C15	−0.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.54	3.283 (3)	145

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄ClNOS
M_r	351.83
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	6.3171 (13), 14.535 (3), 18.169 (4)
β (°)	96.85 (3)
V (Å³)	1656.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.15 × 0.09 × 0.07

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.963, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	16788, 3788, 2287
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.129, 1.04
No. of reflections	3788
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.31

Computer programs: CrystalClear (Rigaku, 2000), CrystalStructure (Rigaku/MSC, 2003), 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
N1—H1A···O1ⁱ	0.86	2.54	3.283 (3)	145.1

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

The authors thank Dr Chunling Shi for the help with the crystal structure analysis

References

Ashmore, J., Bishop, R., Craig, D. C. & Scudder, M. L. (2008). Acta Cryst. E64, o1136. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dodeigne, C., Thunus, L. & Lejeune, R. (2000). Talanta, 51, 415–439. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2000). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2003). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, 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
Zomer, G. & Jacquemijns, M. (2001). Chemiluminescence in Analytical Chemistry, edited by A. M. Garcia-Campana & W. R. G. Baeyens, pp. 529–549. New York: Marcel Dekker. Google Scholar