2,4-Bis(2-bromo­phen­yl)-3-aza­bicyclo­[3.3.1]nonan-9-one

Parthiban, P.; Ramkumar, V.; Kim, M.S.; Son, S.M.; Jeong, Y.T.

doi:10.1107/S1600536808037501

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2385

doi:10.1107/S1600536808037501

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2,4-Bis(2-bromophenyl)-3-azabicyclo[3.3.1]nonan-9-one

P. Parthiban,^a V. Ramkumar,^b Min Sung Kim,^a Se Mo Son ^a and Yeon Tae Jeong ^a ^*

^aDivision of Image Science and Information Engineering, Pukyong National University, Busan 608 739, Republic of Korea, and ^bDepartment of Chemistry, IIT Madras, Chennai, Tamilnadu, India
^*Correspondence e-mail: ytjeong@pknu.ac.kr

(Received 10 November 2008; accepted 12 November 2008; online 20 November 2008)

In the molecular structure of the title compound, C₂₀H₁₉Br₂NO, the fused six-membered heterocyclic and cyclohexane rings adopt a twin-chair conformation with equatorial orientations of all the substituents. Both the ortho-bromo substituents of the benzene rings are oriented towards the carbonyl group; the dihedral angle between the ring planes is 29.13 (3)°. In the crystal structure, the N—H group does not participate in any hydrogen bonds.

Related literature

For 3-azabicyclononan-9-ones and their significance as bio-active molecules, see: Barker et al. (2005 ); Jeyaraman & Avila (1981 ). For puckering parameters, see: Cremer & Pople (1975 ); Web & Becker (1967 ). For a similiar structure see; Parthiban et al. (2008 ).

Experimental

Crystal data

C₂₀H₁₉Br₂NO
M_r = 449.18
Triclinic, $[P \overline 1]$
a = 7.8389 (3) Å
b = 10.5770 (3) Å
c = 11.0274 (3) Å
α = 101.099 (2)°
β = 93.725 (2)°
γ = 97.399 (1)°
V = 885.94 (5) Å³
Z = 2
Mo Kα radiation
μ = 4.58 mm⁻¹
T = 298 (2) K
0.45 × 0.38 × 0.35 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.232, T_max = 0.297 (expected range = 0.157–0.201)
10959 measured reflections
4098 independent reflections
3266 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.060
S = 1.00
4098 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037501/hb2843sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037501/hb2843Isup2.hkl

checkCIF report

Comment top

3-Azabicyclononan-9-ones are important class of compounds due to their significance as bio-active molecules (Jeyaraman & Avila, 1981; Barker et al., 2005).

The title compound, (I), exists in a chair–chair conformation with equatorial orientations of the ortho bromo-phenyl groups on each side of the secondary amino group with the torsion angles of C8—C2—C1—C9 and C8—C6—C7—C15 being 177.88 (4) and 179.42 (6)°, respectively. In both aryl groups, the bromo substituents point towards the carbonyl group and the dihedral angle between the ring planes is 29.13 (3)°. The piperidine ring adopts near ideal chair conformation with the deviation of ring atoms N1 and C8 from the C1/C2/C6/C7 plane by -0.635 (3)and 0.705 (3)Å, respectively, Q_T = 0.599 (2)Å, q(2)=0.047 (2)Å, q(3)=0.597 (2)Å, θ = 4.71 (19)° Cremer & Pople, 1975; Web & Becker, 1967), whereas the cyclohexane ring atoms C4 and C8 deviate from the C2/C3/C5/C6 plane by -0.539 (4) and 0.725 (3)Å, respectively, Q_T = 0.565 (2)Å, q(2)=0.141 (2)Å, q(3)=0.548 (2)Å, θ = 14.4 (2)°, indicating a deviation from the ideal chair conformation of the cyclohexane part in the title compound. The crystal structure is stabilized by the intermolecular van der Waals interactions.

Related literature top

For 3-azabicyclononan-9-ones and their significance as bio-active molecules, see: Barker et al. (2005); Jeyaraman & Avila (1981). For puckering parameters, see: Cremer & Pople (1975); Web & Becker (1967). For a similiar structure see; Parthiban et al. (2008).

Experimental top

A mixture of cyclohexanone (0.05 mol) and ortho bromobenzaldehyde (0.1 mol) was added to a warm solution of ammonium acetate (0.075 mol) in 50 ml of absolute ethanol. The mixture was gently warmed on a hot plate until a yellow colour was formed and then cooled to room temperature. Then, 50 ml of ether was added and allowed to stir over night at room temperature. At the end, the crude azabicyclic ketone was separated by filtration and washed with 1:5 v/v ethanol–ether mixture till the solid became colourless. Recrystallization of the compound from acetone gave colourless blocks of (I).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with non-hydrogen atoms represented as 30% probability ellipsoids.

2,4-Bis(2-bromophenyl)-3-azabicyclo[3.3.1]nonan-9-one top

Crystal data top

C₂₀H₁₉Br₂NO	Z = 2
M_r = 449.18	F(000) = 448
Triclinic, P1	D_x = 1.684 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8389 (3) Å	Cell parameters from 5642 reflections
b = 10.5770 (3) Å	θ = 2.5–28.2°
c = 11.0274 (3) Å	µ = 4.58 mm⁻¹
α = 101.099 (2)°	T = 298 K
β = 93.725 (2)°	Block, colourless
γ = 97.399 (1)°	0.45 × 0.38 × 0.35 mm
V = 885.94 (5) Å³

Data collection top

Bruker APEXII CCD diffractometer	4098 independent reflections
Radiation source: fine-focus sealed tube	3266 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −10→10
T_min = 0.232, T_max = 0.297	k = −13→13
10959 measured reflections	l = −14→14

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0207P)² + 0.5638P] where P = (F_o² + 2F_c²)/3
4098 reflections	(Δ/σ)_max = 0.002
221 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₂₀H₁₉Br₂NO	γ = 97.399 (1)°
M_r = 449.18	V = 885.94 (5) Å³
Triclinic, P1	Z = 2
a = 7.8389 (3) Å	Mo Kα radiation
b = 10.5770 (3) Å	µ = 4.58 mm⁻¹
c = 11.0274 (3) Å	T = 298 K
α = 101.099 (2)°	0.45 × 0.38 × 0.35 mm
β = 93.725 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4098 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	3266 reflections with I > 2σ(I)
T_min = 0.232, T_max = 0.297	R_int = 0.017
10959 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.58 e Å⁻³
4098 reflections	Δρ_min = −0.56 e Å⁻³
221 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	−0.00438 (3)	0.47719 (2)	0.77681 (2)	0.05065 (8)
Br2	0.16949 (3)	1.23193 (3)	1.01448 (2)	0.06070 (9)
C1	0.2124 (2)	0.74756 (18)	0.75331 (18)	0.0301 (4)
H1	0.1437	0.7370	0.8228	0.036*
C2	0.0889 (2)	0.76537 (19)	0.64395 (19)	0.0344 (4)
H2	−0.0049	0.6918	0.6254	0.041*
C3	0.1735 (3)	0.7773 (2)	0.5238 (2)	0.0428 (5)
H3A	0.2294	0.7011	0.4980	0.051*
H3B	0.0839	0.7778	0.4591	0.051*
C4	0.3064 (3)	0.8987 (2)	0.5360 (2)	0.0432 (5)
H4A	0.4119	0.8865	0.5806	0.052*
H4B	0.3333	0.9102	0.4539	0.052*
C5	0.2434 (3)	1.0214 (2)	0.60396 (19)	0.0392 (5)
H5A	0.1647	1.0500	0.5468	0.047*
H5B	0.3418	1.0895	0.6280	0.047*
C6	0.1515 (2)	1.00528 (19)	0.72040 (18)	0.0331 (4)
H6	0.0967	1.0828	0.7479	0.040*
C7	0.2692 (2)	0.98341 (18)	0.83118 (17)	0.0294 (4)
H7	0.1987	0.9747	0.9001	0.035*
C8	0.0132 (2)	0.8886 (2)	0.68529 (18)	0.0342 (4)
C9	0.3014 (2)	0.62834 (18)	0.72007 (17)	0.0304 (4)
C10	0.4692 (3)	0.6383 (2)	0.6847 (2)	0.0389 (5)
H10	0.5265	0.7194	0.6796	0.047*
C11	0.5525 (3)	0.5302 (2)	0.6570 (2)	0.0495 (6)
H11	0.6641	0.5392	0.6328	0.059*
C12	0.4711 (3)	0.4095 (2)	0.6651 (2)	0.0556 (6)
H12	0.5280	0.3371	0.6472	0.067*
C13	0.3055 (3)	0.3958 (2)	0.6995 (2)	0.0482 (6)
H13	0.2496	0.3142	0.7047	0.058*
C14	0.2228 (3)	0.50413 (19)	0.72632 (19)	0.0350 (4)
C15	0.4125 (2)	1.09742 (18)	0.87430 (17)	0.0290 (4)
C16	0.3860 (3)	1.21258 (19)	0.95107 (18)	0.0337 (4)
C17	0.5159 (3)	1.3181 (2)	0.9863 (2)	0.0436 (5)
H17	0.4946	1.3938	1.0380	0.052*
C18	0.6757 (3)	1.3104 (2)	0.9446 (2)	0.0499 (6)
H18	0.7629	1.3812	0.9670	0.060*
C19	0.7071 (3)	1.1976 (2)	0.8696 (2)	0.0482 (6)
H19	0.8161	1.1920	0.8421	0.058*
C20	0.5772 (3)	1.0923 (2)	0.8347 (2)	0.0381 (5)
H20	0.6003	1.0166	0.7839	0.046*
N1	0.3422 (2)	0.86343 (15)	0.79409 (16)	0.0304 (4)
O1	−0.13950 (19)	0.89419 (17)	0.68681 (16)	0.0521 (4)
H1A	0.407 (3)	0.851 (2)	0.850 (2)	0.040 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04366 (13)	0.03775 (13)	0.06740 (17)	−0.00469 (9)	0.01281 (11)	0.00737 (11)
Br2	0.05389 (15)	0.06429 (18)	0.05949 (17)	0.02181 (12)	0.01497 (12)	−0.01039 (13)
C1	0.0296 (9)	0.0256 (10)	0.0349 (10)	0.0042 (7)	0.0038 (8)	0.0056 (8)
C2	0.0286 (9)	0.0300 (10)	0.0415 (11)	0.0019 (8)	−0.0038 (8)	0.0035 (9)
C3	0.0511 (13)	0.0398 (12)	0.0351 (11)	0.0125 (10)	−0.0022 (10)	−0.0001 (9)
C4	0.0505 (13)	0.0492 (13)	0.0325 (11)	0.0104 (10)	0.0097 (9)	0.0107 (10)
C5	0.0441 (11)	0.0369 (12)	0.0386 (12)	0.0063 (9)	−0.0008 (9)	0.0138 (9)
C6	0.0326 (10)	0.0299 (10)	0.0371 (11)	0.0102 (8)	0.0012 (8)	0.0046 (8)
C7	0.0300 (9)	0.0276 (10)	0.0302 (10)	0.0044 (7)	0.0033 (7)	0.0049 (8)
C8	0.0310 (9)	0.0405 (12)	0.0327 (11)	0.0088 (8)	−0.0003 (8)	0.0100 (9)
C9	0.0335 (9)	0.0278 (10)	0.0295 (10)	0.0060 (8)	0.0003 (8)	0.0046 (8)
C10	0.0357 (10)	0.0380 (12)	0.0448 (12)	0.0081 (9)	0.0059 (9)	0.0104 (9)
C11	0.0417 (12)	0.0553 (15)	0.0575 (15)	0.0220 (11)	0.0123 (11)	0.0135 (12)
C12	0.0657 (16)	0.0446 (14)	0.0637 (16)	0.0311 (12)	0.0140 (13)	0.0109 (12)
C13	0.0608 (15)	0.0297 (12)	0.0551 (14)	0.0101 (10)	0.0065 (11)	0.0083 (10)
C14	0.0371 (10)	0.0304 (10)	0.0362 (11)	0.0041 (8)	0.0025 (8)	0.0038 (8)
C15	0.0314 (9)	0.0280 (10)	0.0284 (10)	0.0053 (8)	0.0005 (7)	0.0079 (8)
C16	0.0403 (10)	0.0322 (11)	0.0297 (10)	0.0100 (8)	0.0010 (8)	0.0062 (8)
C17	0.0646 (15)	0.0278 (11)	0.0353 (12)	0.0034 (10)	−0.0054 (10)	0.0047 (9)
C18	0.0547 (14)	0.0427 (13)	0.0455 (13)	−0.0154 (11)	−0.0072 (11)	0.0108 (11)
C19	0.0346 (11)	0.0573 (15)	0.0500 (14)	−0.0043 (10)	0.0028 (10)	0.0117 (12)
C20	0.0337 (10)	0.0375 (11)	0.0411 (12)	0.0048 (9)	0.0047 (9)	0.0029 (9)
N1	0.0292 (8)	0.0249 (8)	0.0362 (9)	0.0055 (6)	−0.0050 (7)	0.0053 (7)
O1	0.0292 (7)	0.0588 (11)	0.0693 (11)	0.0119 (7)	0.0028 (7)	0.0120 (9)

Geometric parameters (Å, º) top

Br1—C14	1.903 (2)	C7—H7	0.9800
Br2—C16	1.897 (2)	C8—O1	1.207 (2)
C1—N1	1.465 (2)	C9—C10	1.393 (3)
C1—C9	1.515 (3)	C9—C14	1.394 (3)
C1—C2	1.552 (3)	C10—C11	1.382 (3)
C1—H1	0.9800	C10—H10	0.9300
C2—C8	1.505 (3)	C11—C12	1.373 (4)
C2—C3	1.539 (3)	C11—H11	0.9300
C2—H2	0.9800	C12—C13	1.373 (3)
C3—C4	1.524 (3)	C12—H12	0.9300
C3—H3A	0.9700	C13—C14	1.381 (3)
C3—H3B	0.9700	C13—H13	0.9300
C4—C5	1.525 (3)	C15—C20	1.393 (3)
C4—H4A	0.9700	C15—C16	1.391 (3)
C4—H4B	0.9700	C16—C17	1.387 (3)
C5—C6	1.539 (3)	C17—C18	1.369 (3)
C5—H5A	0.9700	C17—H17	0.9300
C5—H5B	0.9700	C18—C19	1.375 (4)
C6—C8	1.506 (3)	C18—H18	0.9300
C6—C7	1.554 (3)	C19—C20	1.385 (3)
C6—H6	0.9800	C19—H19	0.9300
C7—N1	1.457 (2)	C20—H20	0.9300
C7—C15	1.518 (2)	N1—H1A	0.81 (2)

N1—C1—C9	109.63 (15)	O1—C8—C2	124.48 (19)
N1—C1—C2	110.38 (16)	O1—C8—C6	123.98 (19)
C9—C1—C2	112.32 (16)	C2—C8—C6	111.51 (16)
N1—C1—H1	108.1	C10—C9—C14	116.51 (18)
C9—C1—H1	108.1	C10—C9—C1	121.26 (17)
C2—C1—H1	108.1	C14—C9—C1	122.21 (17)
C8—C2—C3	107.21 (17)	C11—C10—C9	121.5 (2)
C8—C2—C1	107.83 (16)	C11—C10—H10	119.3
C3—C2—C1	115.42 (16)	C9—C10—H10	119.3
C8—C2—H2	108.7	C12—C11—C10	120.3 (2)
C3—C2—H2	108.7	C12—C11—H11	119.9
C1—C2—H2	108.7	C10—C11—H11	119.9
C4—C3—C2	114.03 (17)	C13—C12—C11	119.9 (2)
C4—C3—H3A	108.7	C13—C12—H12	120.1
C2—C3—H3A	108.7	C11—C12—H12	120.1
C4—C3—H3B	108.7	C12—C13—C14	119.5 (2)
C2—C3—H3B	108.7	C12—C13—H13	120.3
H3A—C3—H3B	107.6	C14—C13—H13	120.3
C5—C4—C3	112.67 (18)	C13—C14—C9	122.3 (2)
C5—C4—H4A	109.1	C13—C14—Br1	116.76 (16)
C3—C4—H4A	109.1	C9—C14—Br1	120.89 (15)
C5—C4—H4B	109.1	C20—C15—C16	116.80 (18)
C3—C4—H4B	109.1	C20—C15—C7	120.81 (17)
H4A—C4—H4B	107.8	C16—C15—C7	122.36 (17)
C4—C5—C6	114.82 (17)	C17—C16—C15	122.0 (2)
C4—C5—H5A	108.6	C17—C16—Br2	116.64 (16)
C6—C5—H5A	108.6	C15—C16—Br2	121.32 (15)
C4—C5—H5B	108.6	C18—C17—C16	119.7 (2)
C6—C5—H5B	108.6	C18—C17—H17	120.2
H5A—C5—H5B	107.5	C16—C17—H17	120.2
C8—C6—C5	108.13 (16)	C17—C18—C19	119.9 (2)
C8—C6—C7	107.18 (16)	C17—C18—H18	120.0
C5—C6—C7	115.25 (16)	C19—C18—H18	120.0
C8—C6—H6	108.7	C18—C19—C20	120.3 (2)
C5—C6—H6	108.7	C18—C19—H19	119.9
C7—C6—H6	108.7	C20—C19—H19	119.9
N1—C7—C15	110.21 (15)	C19—C20—C15	121.3 (2)
N1—C7—C6	109.31 (15)	C19—C20—H20	119.3
C15—C7—C6	111.09 (15)	C15—C20—H20	119.3
N1—C7—H7	108.7	C7—N1—C1	113.89 (15)
C15—C7—H7	108.7	C7—N1—H1A	111.0 (16)
C6—C7—H7	108.7	C1—N1—H1A	108.6 (16)

N1—C1—C2—C8	−55.2 (2)	C9—C10—C11—C12	−0.6 (4)
C9—C1—C2—C8	−177.89 (16)	C10—C11—C12—C13	0.7 (4)
N1—C1—C2—C3	64.6 (2)	C11—C12—C13—C14	−0.3 (4)
C9—C1—C2—C3	−58.1 (2)	C12—C13—C14—C9	−0.2 (3)
C8—C2—C3—C4	55.1 (2)	C12—C13—C14—Br1	−178.65 (19)
C1—C2—C3—C4	−65.0 (2)	C10—C9—C14—C13	0.2 (3)
C2—C3—C4—C5	−45.4 (3)	C1—C9—C14—C13	−178.10 (19)
C3—C4—C5—C6	43.4 (3)	C10—C9—C14—Br1	178.65 (15)
C4—C5—C6—C8	−51.3 (2)	C1—C9—C14—Br1	0.3 (3)
C4—C5—C6—C7	68.6 (2)	N1—C7—C15—C20	23.6 (2)
C8—C6—C7—N1	58.74 (19)	C6—C7—C15—C20	−97.7 (2)
C5—C6—C7—N1	−61.6 (2)	N1—C7—C15—C16	−158.48 (18)
C8—C6—C7—C15	−179.43 (15)	C6—C7—C15—C16	80.2 (2)
C5—C6—C7—C15	60.2 (2)	C20—C15—C16—C17	0.5 (3)
C3—C2—C8—O1	113.0 (2)	C7—C15—C16—C17	−177.53 (18)
C1—C2—C8—O1	−122.1 (2)	C20—C15—C16—Br2	−178.76 (15)
C3—C2—C8—C6	−64.9 (2)	C7—C15—C16—Br2	3.2 (3)
C1—C2—C8—C6	59.9 (2)	C15—C16—C17—C18	0.3 (3)
C5—C6—C8—O1	−114.9 (2)	Br2—C16—C17—C18	179.52 (17)
C7—C6—C8—O1	120.3 (2)	C16—C17—C18—C19	−0.9 (3)
C5—C6—C8—C2	63.1 (2)	C17—C18—C19—C20	0.8 (4)
C7—C6—C8—C2	−61.7 (2)	C18—C19—C20—C15	0.0 (3)
N1—C1—C9—C10	−24.4 (3)	C16—C15—C20—C19	−0.6 (3)
C2—C1—C9—C10	98.7 (2)	C7—C15—C20—C19	177.4 (2)
N1—C1—C9—C14	153.82 (18)	C15—C7—N1—C1	178.86 (15)
C2—C1—C9—C14	−83.1 (2)	C6—C7—N1—C1	−58.8 (2)
C14—C9—C10—C11	0.2 (3)	C9—C1—N1—C7	−178.59 (16)
C1—C9—C10—C11	178.5 (2)	C2—C1—N1—C7	57.2 (2)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉Br₂NO
M_r	449.18
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.8389 (3), 10.5770 (3), 11.0274 (3)
α, β, γ (°)	101.099 (2), 93.725 (2), 97.399 (1)
V (Å³)	885.94 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.58
Crystal size (mm)	0.45 × 0.38 × 0.35

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.232, 0.297
No. of measured, independent and observed [I > 2σ(I)] reflections	10959, 4098, 3266
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.060, 1.00
No. of reflections	4098
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.56

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Acknowledgements

The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

References

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