5-Bromo-5-bromo­methyl-2-phen­oxy-1,3,2-dioxaphospho­rinan-2-one

Fun, H.-K.; Chantrapromma, S.; Adak, A.K.; Maity, A.C.; Goswami, S.

doi:10.1107/S1600536808033631

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Pages o2228-o2229

doi:10.1107/S1600536808033631

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5-Bromo-5-bromomethyl-2-phenoxy-1,3,2-dioxaphosphorinan-2-one

Hoong-Kun Fun,^a ^* Suchada Chantrapromma,^b ‡ Avijit Kr. Adak,^c Annada C. Maity ^d and Shyamaprosad Goswami ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^cDepartment of Chemistry, Purdue University, West Lafayette, IN 47907, USA, and ^dDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
^*Correspondence e-mail: hkfun@usm.my

(Received 12 October 2008; accepted 15 October 2008; online 31 October 2008)

In the title 1,3,2-dioxaphosphorinane derivative, C₁₀H₁₁Br₂O₄P, the 1,3,2-dioxaphosphorinane ring adopts a chair conformation, having the P=O bond equatorially oriented and the phenoxy group axially oriented. The bromo substituent is in an axial position opposite to the phenoxy group and the bromomethyl group is in an equatorial position opposite to the P=O bond. In the crystal packing, molecules are linked through weak C—H⋯O and C—H⋯Br interactions to form chains along the b axis. The chains are arranged into sheets parallel to the ab plane. In adjacent sheets, molecules are arranged in an antiparallel fashion. Intermolecular C—H⋯π interactions are also observed.

Related literature

For values of bond lengths and angles, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring conformations, see: Cremer & Pople (1975 ). For related structures, see, for example: Jones et al. (1984 ); Polozov et al. (1995 ). For related literature and applications of dioxaphosphorinane derivatives, see, for example: Goswami (1993 ); Goswami & Adak (2002 ); Pilato et al. (1991 ); Taylor & Goswami (1992 ).

Experimental

Crystal data

C₁₀H₁₁Br₂O₄P
M_r = 385.96
Monoclinic, P 2₁ /c
a = 12.1315 (3) Å
b = 6.3095 (1) Å
c = 16.8901 (3) Å
β = 92.196 (2)°
V = 1291.88 (4) Å³
Z = 4
Mo Kα radiation
μ = 6.40 mm⁻¹
T = 296 (2) K
0.45 × 0.10 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.156, T_max = 0.726
16007 measured reflections
3756 independent reflections
1952 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.142
S = 0.99
3756 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O3ⁱ	0.97	2.35	3.217 (6)	148
C4—H4A⋯O3ⁱ	0.97	2.53	3.362 (6)	144
C2—H2B⋯Cg1ⁱⁱ	0.97	2.81	3.755 (5)	166
C3—H3C⋯Cg1ⁱⁱⁱ	0.97	2.70	3.560 (5)	148
Symmetry codes: (i) x, y+1, z; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033631/is2349sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033631/is2349Isup2.hkl

checkCIF report

Comment top

Six-membered cyclic phosphates are important constituents present in a number of biologically important molecules e.g. cyclic adenosine monophosphate (cAMP) and the Compound Z, a precursor of the molybdenum cofactor (Moco) (Goswami, 1993). They especially play key roles in many biosynthetic pathways and comprise structural sub-units of many physiologically important materials. In our synthetic studies (Pilato et al., 1991; Taylor & Goswami, 1992) on the molybdenum cofactor, we are interested to have an efficient synthesis of cyclic dihydroxyacetone phosphate (CDHAP) (Goswami & Adak, 2002). Reaction of phosphate triesters with N-bromosuccinimide (NBS) results in the formation of a dibromo derivative (Fig. 1).

In the title 1,3,2-dioxaphosphorinane derivative (Fig. 1), C₁₀H₁₁Br₂O₄P, the 1,3,2-dioxaphosphorinane ring adopts a slightly flattened chair conformation with the puckering parameter (Cremer & Pople, 1975) Q = 0.496 (4) Å, θ = 7.4 (5)° and ϕ = 177 (4)°, having the P═O bond equatorially attached and the phenoxy substituent axially attached with the torsion angle O1—P1—O4—O5 = 82.6 (4)°. The orientation of the phenoxy group is not co-planar to the 1,3,2-dioxaphosphorinane ring as can be indicated by the torsion angle P1—O4—C5—C6 of -108.2 (4)°. The bromo substituent is in the opposite axial position to the phenoxy substituent and the methylbromo group is in an opposite equatorial position to the P═O bond. The bond lengths and angles in (I) are within normal ranges (Allen et al., 1987) and are comparable to related structures (Jones et al., 1984; Polozov et al., 1995). The closest Br···Br distance is 3.5484 (9) Å.

In the crystal packing shown in Fig. 2, the molecules are linked through weak C—H···O interactions (Table 1) to form chains along the b axis which generate S(6) ring motifs (Bernstein et al., 1995). The chains are arranged into sheets parallel to the ab plane. In the adjacent sheets, the molecules are arranged in an anti-parallel fashion (Fig. 3). The adjacent sheets are connected through weak C—H···O interactions (Table 1) and Br···Br short contacts with the Br···Br distance of 3.8771 (9) Å (symmetry code: 1 - x, 1/2 + y, 1/2 - z). The crystal is stabilized by weak C—H···O, C—H···Br interactions and C—H···π interactions (Table 1); Cg1 is the centroid of the C5–C10 ring.

Related literature top

For values of bond lengths and angles, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975). For related structures, see, for example: Jones et al. (1984); Polozov et al. (1995). For related literature and applications of dioxaphosphorinane derivatives, see, for example: Goswami (1993); Goswami & Adak (2002); Pilato et al. (1991); Taylor & Goswami (1992).

Experimental top

A solution of 5-methylene-2-oxo-2-phenoxy-[1,3,2]-dioxaphosphorinane (0.4 g, 1.76 mmol), doubly crystallized N-bromosuccinimide (0.38 g, 1.78 mmol) and azobisisobutyronitrile (10 mg) in dry CCl₄ (40 ml) was heated under reflux in the presence of a 60 W lamp for 4 h. By this time, a maximum of 80% of the starting materials were converted into the product. Upon prolonged heating for a period of 8 h, no improvement has been observed with respect to yield nor new spot was observed as monitored by thin layer chromatography. The CCl₄ layer was then stripped off and the gummy material was dissolved in dichloromethane (100 ml) and washed well with water (2 × 100 ml) and then with brine. The organic layer was dried (Na₂SO₄) and concentrated to afford the crude product as a light brown gum which was passed through a silica gel (100–200 mesh) column eluting with dichloromethane to get the pure title compound as a white crystalline solid (0.32 g, 60%; m.p. 361–362 K).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of (I), viewed along the c axis showing chains along the b axis. Hydrogen bonds were shown as dash lines.
	Fig. 3. The crystal packing of (I), viewed along the b axis showing the anti-parallel arrangement of the adjacent sheets. Hydrogen bonds and Br···Br short contact were shown as dash lines.

5-Bromo-5-bromomethyl-2-phenoxy-1,3,2-dioxaphosphorinan-2-one top

Crystal data top

C₁₀H₁₁Br₂O₄P	F(000) = 752
M_r = 385.96	D_x = 1.984 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 361–362 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.1315 (3) Å	Cell parameters from 3756 reflections
b = 6.3095 (1) Å	θ = 2.4–30.0°
c = 16.8901 (3) Å	µ = 6.40 mm⁻¹
β = 92.196 (2)°	T = 296 K
V = 1291.88 (4) Å³	Needle, colourless
Z = 4	0.45 × 0.10 × 0.05 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3756 independent reflections
Radiation source: fine-focus sealed tube	1952 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 2.4°
ω scans	h = −15→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
T_min = 0.156, T_max = 0.726	l = −22→23
16007 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0636P)² + 0.3299P] where P = (F_o² + 2F_c²)/3
3756 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.91 e Å⁻³

Crystal data top

C₁₀H₁₁Br₂O₄P	V = 1291.88 (4) Å³
M_r = 385.96	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1315 (3) Å	µ = 6.40 mm⁻¹
b = 6.3095 (1) Å	T = 296 K
c = 16.8901 (3) Å	0.45 × 0.10 × 0.05 mm
β = 92.196 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3756 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1952 reflections with I > 2σ(I)
T_min = 0.156, T_max = 0.726	R_int = 0.072
16007 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 0.99	Δρ_max = 0.67 e Å⁻³
3756 reflections	Δρ_min = −0.91 e Å⁻³
154 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
Br1	0.60424 (5)	0.36096 (9)	0.21315 (3)	0.0610 (2)
Br2	0.53167 (5)	0.78769 (10)	0.08461 (4)	0.0719 (2)
P1	0.88523 (11)	0.20179 (19)	0.12969 (8)	0.0438 (3)
O1	0.8686 (3)	0.3316 (5)	0.20749 (18)	0.0463 (8)
O2	0.7744 (3)	0.2261 (5)	0.0802 (2)	0.0495 (8)
O3	0.9159 (3)	−0.0157 (5)	0.1448 (3)	0.0677 (11)
O4	0.9665 (3)	0.3340 (5)	0.0784 (2)	0.0504 (8)
C1	0.7093 (4)	0.5327 (6)	0.1542 (3)	0.0376 (10)
C2	0.8186 (4)	0.5375 (7)	0.2016 (3)	0.0443 (11)
H2A	0.8687	0.6340	0.1764	0.053*
H2B	0.8063	0.5908	0.2544	0.053*
C3	0.7229 (4)	0.4330 (7)	0.0740 (3)	0.0453 (11)
H3B	0.6511	0.4192	0.0472	0.054*
H3C	0.7677	0.5250	0.0422	0.054*
C4	0.6653 (4)	0.7573 (7)	0.1467 (3)	0.0519 (13)
H4A	0.7214	0.8449	0.1235	0.062*
H4B	0.6535	0.8115	0.1994	0.062*
C5	1.0807 (4)	0.3235 (7)	0.0921 (3)	0.0408 (11)
C6	1.1335 (5)	0.4950 (9)	0.1258 (3)	0.0619 (15)
H6A	1.0939	0.6132	0.1413	0.074*
C7	1.2469 (6)	0.4884 (12)	0.1362 (3)	0.077 (2)
H7A	1.2841	0.6040	0.1585	0.092*
C8	1.3055 (5)	0.3123 (14)	0.1139 (3)	0.077 (2)
H8A	1.3817	0.3087	0.1217	0.092*
C9	1.2510 (5)	0.1428 (10)	0.0803 (3)	0.0640 (16)
H9A	1.2904	0.0241	0.0651	0.077*
C10	1.1368 (4)	0.1479 (8)	0.0688 (3)	0.0494 (12)
H10A	1.0993	0.0336	0.0458	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0439 (3)	0.0719 (4)	0.0680 (4)	−0.0032 (3)	0.0128 (3)	0.0258 (3)
Br2	0.0560 (4)	0.0786 (4)	0.0810 (5)	0.0177 (3)	0.0001 (3)	0.0093 (3)
P1	0.0372 (7)	0.0360 (6)	0.0585 (8)	−0.0025 (5)	0.0049 (6)	0.0049 (5)
O1	0.0419 (19)	0.0494 (18)	0.0472 (19)	0.0009 (15)	−0.0047 (15)	0.0109 (14)
O2	0.048 (2)	0.0423 (17)	0.058 (2)	0.0006 (15)	−0.0007 (17)	−0.0115 (15)
O3	0.056 (2)	0.0374 (18)	0.110 (3)	0.0033 (17)	0.011 (2)	0.0135 (19)
O4	0.0383 (19)	0.0516 (19)	0.062 (2)	0.0020 (15)	0.0096 (16)	0.0124 (16)
C1	0.038 (3)	0.035 (2)	0.040 (2)	−0.0041 (19)	0.006 (2)	0.0020 (18)
C2	0.041 (3)	0.047 (3)	0.044 (3)	0.001 (2)	−0.003 (2)	−0.004 (2)
C3	0.040 (3)	0.052 (3)	0.043 (3)	0.001 (2)	−0.005 (2)	0.000 (2)
C4	0.044 (3)	0.041 (3)	0.070 (4)	−0.001 (2)	−0.002 (3)	−0.001 (2)
C5	0.039 (3)	0.046 (3)	0.037 (2)	−0.007 (2)	0.008 (2)	0.0027 (19)
C6	0.076 (4)	0.056 (3)	0.055 (3)	−0.022 (3)	0.020 (3)	−0.009 (3)
C7	0.082 (5)	0.097 (5)	0.050 (3)	−0.048 (4)	−0.001 (3)	−0.007 (3)
C8	0.048 (4)	0.137 (6)	0.045 (3)	−0.029 (4)	−0.008 (3)	0.022 (4)
C9	0.049 (3)	0.088 (4)	0.055 (3)	0.010 (3)	0.004 (3)	0.014 (3)
C10	0.043 (3)	0.058 (3)	0.048 (3)	−0.005 (2)	0.004 (2)	−0.003 (2)

Geometric parameters (Å, º) top

Br1—C1	1.971 (4)	C3—H3C	0.9700
Br2—C4	1.907 (5)	C4—H4A	0.9700
P1—O3	1.442 (4)	C4—H4B	0.9700
P1—O2	1.563 (4)	C5—C10	1.365 (7)
P1—O1	1.568 (3)	C5—C6	1.371 (7)
P1—O4	1.576 (3)	C6—C7	1.380 (9)
O1—C2	1.436 (5)	C6—H6A	0.9300
O2—C3	1.450 (6)	C7—C8	1.380 (10)
O4—C5	1.398 (6)	C7—H7A	0.9300
C1—C3	1.509 (6)	C8—C9	1.369 (9)
C1—C4	1.518 (6)	C8—H8A	0.9300
C1—C2	1.523 (6)	C9—C10	1.392 (8)
C2—H2A	0.9700	C9—H9A	0.9300
C2—H2B	0.9700	C10—H10A	0.9300
C3—H3B	0.9700

O3—P1—O2	113.5 (2)	H3B—C3—H3C	107.9
O3—P1—O1	112.9 (2)	C1—C4—Br2	115.4 (3)
O2—P1—O1	105.14 (18)	C1—C4—H4A	108.4
O3—P1—O4	116.0 (2)	Br2—C4—H4A	108.4
O2—P1—O4	101.35 (19)	C1—C4—H4B	108.4
O1—P1—O4	106.73 (19)	Br2—C4—H4B	108.4
C2—O1—P1	118.8 (3)	H4A—C4—H4B	107.5
C3—O2—P1	119.1 (3)	C10—C5—C6	122.0 (5)
C5—O4—P1	121.4 (3)	C10—C5—O4	119.5 (4)
C3—C1—C4	111.3 (4)	C6—C5—O4	118.4 (5)
C3—C1—C2	110.9 (4)	C5—C6—C7	118.5 (6)
C4—C1—C2	108.8 (4)	C5—C6—H6A	120.8
C3—C1—Br1	108.6 (3)	C7—C6—H6A	120.8
C4—C1—Br1	108.9 (3)	C8—C7—C6	120.7 (6)
C2—C1—Br1	108.2 (3)	C8—C7—H7A	119.6
O1—C2—C1	112.0 (4)	C6—C7—H7A	119.6
O1—C2—H2A	109.2	C9—C8—C7	119.8 (6)
C1—C2—H2A	109.2	C9—C8—H8A	120.1
O1—C2—H2B	109.2	C7—C8—H8A	120.1
C1—C2—H2B	109.2	C8—C9—C10	120.1 (6)
H2A—C2—H2B	107.9	C8—C9—H9A	120.0
O2—C3—C1	111.8 (4)	C10—C9—H9A	120.0
O2—C3—H3B	109.3	C5—C10—C9	118.9 (5)
C1—C3—H3B	109.3	C5—C10—H10A	120.5
O2—C3—H3C	109.3	C9—C10—H10A	120.5
C1—C3—H3C	109.3

O3—P1—O1—C2	−168.7 (3)	C2—C1—C3—O2	53.4 (5)
O2—P1—O1—C2	−44.4 (4)	Br1—C1—C3—O2	−65.5 (4)
O4—P1—O1—C2	62.7 (4)	C3—C1—C4—Br2	54.6 (5)
O3—P1—O2—C3	168.0 (3)	C2—C1—C4—Br2	177.1 (3)
O1—P1—O2—C3	44.1 (4)	Br1—C1—C4—Br2	−65.2 (4)
O4—P1—O2—C3	−66.9 (4)	P1—O4—C5—C10	74.5 (5)
O3—P1—O4—C5	−44.2 (4)	P1—O4—C5—C6	−108.2 (4)
O2—P1—O4—C5	−167.6 (3)	C10—C5—C6—C7	0.0 (8)
O1—P1—O4—C5	82.6 (4)	O4—C5—C6—C7	−177.3 (4)
P1—O1—C2—C1	52.5 (5)	C5—C6—C7—C8	−0.6 (9)
C3—C1—C2—O1	−54.0 (5)	C6—C7—C8—C9	0.7 (9)
C4—C1—C2—O1	−176.7 (4)	C7—C8—C9—C10	−0.2 (9)
Br1—C1—C2—O1	65.1 (4)	C6—C5—C10—C9	0.4 (7)
P1—O2—C3—C1	−52.0 (5)	O4—C5—C10—C9	177.7 (4)
C4—C1—C3—O2	174.6 (4)	C8—C9—C10—C5	−0.4 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3ⁱ	0.97	2.35	3.217 (6)	148
C3—H3B···Br2	0.97	2.82	3.233 (5)	106
C4—H4A···O3ⁱ	0.97	2.53	3.362 (6)	144
C2—H2B···Cg1ⁱⁱ	0.97	2.81	3.755 (5)	166
C3—H3C···Cg1ⁱⁱⁱ	0.97	2.70	3.560 (5)	148

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁Br₂O₄P
M_r	385.96
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.1315 (3), 6.3095 (1), 16.8901 (3)
β (°)	92.196 (2)
V (Å³)	1291.88 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.40
Crystal size (mm)	0.45 × 0.10 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.156, 0.726
No. of measured, independent and observed [I > 2σ(I)] reflections	16007, 3756, 1952
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.142, 0.99
No. of reflections	3756
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.91

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3ⁱ	0.97	2.3497	3.217 (6)	148
C3—H3B···Br2	0.97	2.8239	3.233 (5)	106
C4—H4A···O3ⁱ	0.97	2.5309	3.362 (6)	144
C2—H2B···Cg1ⁱⁱ	0.97	2.8055	3.755 (5)	166
C3—H3C···Cg1ⁱⁱⁱ	0.97	2.7027	3.560 (5)	148

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

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

AKA, ACM and SG acknowledge the DST (grant No. SR/S1/OC-13/2005), Government of India, for financial support. ACM thanks the UGC, Government of India, for a fellowship. The authors also thank the Universiti Sains Malaysia for Research University Golden Goose Grant No. 1001/PFIZIK/811012.

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