4′-(4-Bromo­phen­yl)-1′-methyl­dispiro­[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Wei, A.C.; Ali, M.A.; Ismail, R.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536811044515

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3124

doi:10.1107/S1600536811044515

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4′-(4-Bromophenyl)-1′-methyldispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Ang Chee Wei,^a Mohamed Ashraf Ali,^a Rusli Ismail,^a Madhukar Hemamalini ^b and Hoong-Kun Fun ^b ^*‡

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 19 October 2011; accepted 25 October 2011; online 29 October 2011)

In the title compound, C₂₇H₂₀BrNO₃, the pyrrolidine ring adopts a half-chair conformation, while the other five-membered rings adopt flattened envelope conformations with the spiro C atoms as the flap atoms. An intramolecular C—H⋯O hydrogen bond occurs, generating an S(6) ring. In the crystal, molecules are connected via weak C—H⋯O hydrogen bonds, forming chains along the c axis.

Related literature

For background to tuberculosis, see: Sunduru et al. (2010 ); Trivedi et al. (2010 ). For background to anti-tuberculous drugs, see: Moraski et al. (2011 ); Kumar et al. (2009 ); Maheswari et al. (2010 ). For puckering parameters, see: Cremer & Pople (1975 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₇H₂₀BrNO₃
M_r = 486.35
Monoclinic, P 2₁ /n
a = 7.8392 (1) Å
b = 21.5849 (5) Å
c = 12.7823 (3) Å
β = 98.422 (1)°
V = 2139.55 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.95 mm⁻¹
T = 100 K
0.42 × 0.20 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.492, T_max = 0.788
18795 measured reflections
6300 independent reflections
4709 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.094
S = 1.02
6300 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O1	0.99	2.40	3.053 (2)	123
C15—H15A⋯O2ⁱ	0.95	2.44	3.163 (3)	133
C22—H22A⋯O3ⁱ	0.95	2.57	3.225 (3)	126
Symmetry code: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811044515/hb6460sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044515/hb6460Isup2.hkl

checkCIF report

Comment top

Tuberculosis (TB) is one of the most common chronic infections caused by Mycobacterium tuberculosis and is the world's second common cause of death from infectious diseases after AIDS (Sunduru et al., 2010). Among HIV infected patients, TB is the leading killer epidemic. About 2 million people living with HIV/AIDS die from TB every year (Trivedi et al., 2010). To make things even worse, the emergence of multiple drug resistant TB (MDR-TB), extensively drug resistant TB (XDR-TB) and extremely drug resistant TB (XXDR-TB) are on the rise (Moraski et al., 2011). These lead to the need for development of more potent drugs of new structures and with novel mechanisms of action (Trivedi et al., 2010). In our study, spiro nuclei were used as the core structure due to their potential antimycobacterial properties. Some studies have shown that many of these compounds displayed comparable or even better activities than some of the first-line TB drugs (Kumar et al., 2009; Maheswari et al., 2010).

The asymmetric unit of the title compound is shown in Fig. 1. The pyrrolidine ring (N1/C7–C10) is twisted about the C9–C10 bond, with puckering parameters (Cremer & Pople, 1975) Q = 0.449 (2) Å and f = 317.8 (3)°, and adopting a half-chair conformation. The two five- membered carbocyclic rings, C9/C19,C20/C25,C26 and C10–C12/C17–C18, are in envelope conformations: puckering parameters Q = 0.222 (2) Å and f = 182.7 (5)° with atom C9 at the flap; and Q = 0.216 (2) Å and f = 4.9 (5)° with atom C10 at the flap, respectively.

In the crystal packing, (Fig. 2), the molecules are connected via weak intermolecular C—H···O (Table 1) hydrogen bonds, forming one-dimensional chains along the c-axis.

Related literature top

For background to tuberculosis, see: Sunduru et al. (2010); Trivedi et al. (2010). For background to anti-tuberculous drugs, see: Moraski et al. (2011); Kumar et al. (2009); Maheswari et al. (2010). For puckering parameters, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of (E)-2-(4-bromobenzylidene)-2,3-dihydro-1H-indene-1- one (0.001 mmol), ninhydrin (0.001 mmol) and sarcosine (0.002 mmol) (1:1:2) were dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice. The precipitated solid was filtered, washed with water and recrystallised from petroleum ether–ethyl acetate mixture (1:1) to reveal the title compound as yellow blocks.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound (I). H atoms not involved in hydrogen bonding are omitted.

4'-(4-Bromophenyl)-1'-methyldispiro[indan-2,2'-pyrrolidine-3',2''-indan]- 1,3,1''-trione top

Crystal data top

C₂₇H₂₀BrNO₃	F(000) = 992
M_r = 486.35	D_x = 1.510 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5478 reflections
a = 7.8392 (1) Å	θ = 2.5–29.8°
b = 21.5849 (5) Å	µ = 1.95 mm⁻¹
c = 12.7823 (3) Å	T = 100 K
β = 98.422 (1)°	Block, yellow
V = 2139.55 (8) Å³	0.42 × 0.20 × 0.13 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	6300 independent reflections
Radiation source: fine-focus sealed tube	4709 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 30.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.492, T_max = 0.788	k = −30→21
18795 measured reflections	l = −18→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0387P)² + 1.0757P] where P = (F_o² + 2F_c²)/3
6300 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.78 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

C₂₇H₂₀BrNO₃	V = 2139.55 (8) Å³
M_r = 486.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8392 (1) Å	µ = 1.95 mm⁻¹
b = 21.5849 (5) Å	T = 100 K
c = 12.7823 (3) Å	0.42 × 0.20 × 0.13 mm
β = 98.422 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	6300 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4709 reflections with I > 2σ(I)
T_min = 0.492, T_max = 0.788	R_int = 0.036
18795 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.02	Δρ_max = 0.78 e Å⁻³
6300 reflections	Δρ_min = −0.72 e Å⁻³
290 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.43113 (3)	0.100889 (10)	0.065729 (18)	0.03000 (8)
O1	−0.22936 (19)	−0.10044 (7)	0.55329 (11)	0.0260 (3)
O2	−0.0213 (2)	−0.18954 (7)	0.22339 (11)	0.0276 (3)
O3	−0.4454 (2)	−0.15915 (7)	0.21003 (11)	0.0290 (4)
N1	−0.3407 (2)	−0.04677 (8)	0.34244 (13)	0.0215 (4)
C1	0.2608 (2)	0.05064 (9)	0.11634 (15)	0.0204 (4)
C2	0.1755 (3)	0.07378 (10)	0.19495 (16)	0.0219 (4)
H2A	0.2049	0.1132	0.2254	0.026*
C3	0.0460 (3)	0.03840 (9)	0.22887 (15)	0.0203 (4)
H3A	−0.0139	0.0542	0.2826	0.024*
C4	0.0021 (2)	−0.01977 (9)	0.18553 (14)	0.0176 (4)
C5	0.0949 (3)	−0.04220 (9)	0.10800 (15)	0.0203 (4)
H5A	0.0685	−0.0821	0.0785	0.024*
C6	0.2249 (3)	−0.00746 (10)	0.07308 (15)	0.0222 (4)
H6A	0.2876	−0.0233	0.0207	0.027*
C7	−0.1388 (2)	−0.05921 (9)	0.21992 (15)	0.0188 (4)
H7A	−0.1739	−0.0898	0.1621	0.023*
C8	−0.3039 (3)	−0.02450 (10)	0.23916 (16)	0.0224 (4)
H8A	−0.2846	0.0208	0.2408	0.027*
H8B	−0.4008	−0.0342	0.1828	0.027*
C9	−0.2654 (2)	−0.10771 (9)	0.35915 (15)	0.0185 (4)
C10	−0.0832 (2)	−0.09696 (9)	0.32268 (15)	0.0170 (4)
C11	0.0410 (2)	−0.06671 (9)	0.41356 (15)	0.0182 (4)
H11A	0.1157	−0.0356	0.3859	0.022*
H11B	−0.0239	−0.0464	0.4650	0.022*
C12	0.1463 (2)	−0.12043 (9)	0.46402 (15)	0.0187 (4)
C13	0.2532 (3)	−0.12312 (11)	0.56122 (16)	0.0259 (5)
H13A	0.2694	−0.0878	0.6058	0.031*
C14	0.3353 (3)	−0.17868 (12)	0.59126 (17)	0.0320 (5)
H14A	0.4071	−0.1812	0.6578	0.038*
C15	0.3152 (3)	−0.23066 (12)	0.52644 (18)	0.0316 (5)
H15A	0.3717	−0.2682	0.5495	0.038*
C16	0.2136 (3)	−0.22802 (10)	0.42880 (17)	0.0259 (4)
H16A	0.2018	−0.2629	0.3830	0.031*
C17	0.1288 (2)	−0.17243 (9)	0.39946 (15)	0.0192 (4)
C18	0.0067 (2)	−0.15870 (9)	0.30345 (15)	0.0193 (4)
C19	−0.2491 (2)	−0.13185 (10)	0.47401 (15)	0.0203 (4)
C20	−0.2659 (2)	−0.20008 (10)	0.46840 (15)	0.0193 (4)
C21	−0.2248 (3)	−0.24379 (10)	0.54822 (16)	0.0235 (4)
H21A	−0.1788	−0.2315	0.6180	0.028*
C22	−0.2525 (3)	−0.30551 (11)	0.52318 (17)	0.0270 (5)
H22A	−0.2236	−0.3362	0.5761	0.032*
C23	−0.3230 (3)	−0.32353 (10)	0.42047 (18)	0.0274 (5)
H23A	−0.3429	−0.3662	0.4053	0.033*
C24	−0.3641 (3)	−0.28024 (10)	0.34061 (17)	0.0247 (4)
H24A	−0.4117	−0.2926	0.2711	0.030*
C25	−0.3334 (2)	−0.21820 (10)	0.36564 (15)	0.0202 (4)
C26	−0.3611 (3)	−0.16237 (10)	0.29702 (15)	0.0214 (4)
C27	−0.5213 (3)	−0.04025 (11)	0.35822 (17)	0.0282 (5)
H27A	−0.5346	−0.0545	0.4294	0.042*
H27B	−0.5946	−0.0652	0.3056	0.042*
H27C	−0.5556	0.0034	0.3503	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02737 (12)	0.02655 (12)	0.03979 (13)	0.00148 (9)	0.01733 (9)	0.00830 (10)
O1	0.0272 (8)	0.0313 (8)	0.0191 (7)	−0.0046 (7)	0.0025 (6)	−0.0031 (6)
O2	0.0340 (9)	0.0244 (8)	0.0241 (7)	−0.0011 (7)	0.0026 (6)	−0.0056 (6)
O3	0.0289 (8)	0.0354 (9)	0.0200 (7)	−0.0075 (7)	−0.0057 (6)	0.0027 (6)
N1	0.0155 (8)	0.0263 (9)	0.0232 (8)	0.0029 (7)	0.0047 (7)	0.0042 (7)
C1	0.0166 (9)	0.0225 (10)	0.0228 (10)	0.0027 (8)	0.0052 (7)	0.0073 (8)
C2	0.0239 (10)	0.0184 (10)	0.0240 (10)	0.0013 (8)	0.0056 (8)	0.0018 (8)
C3	0.0213 (10)	0.0209 (10)	0.0203 (9)	0.0041 (8)	0.0079 (8)	0.0013 (8)
C4	0.0163 (9)	0.0194 (9)	0.0164 (8)	0.0026 (7)	0.0001 (7)	0.0046 (7)
C5	0.0214 (10)	0.0198 (10)	0.0192 (9)	0.0039 (8)	0.0012 (8)	0.0005 (8)
C6	0.0223 (10)	0.0253 (10)	0.0199 (9)	0.0067 (8)	0.0061 (8)	0.0020 (8)
C7	0.0169 (9)	0.0202 (10)	0.0187 (9)	0.0002 (8)	0.0009 (7)	0.0021 (7)
C8	0.0166 (10)	0.0268 (11)	0.0236 (10)	0.0014 (8)	0.0021 (8)	0.0071 (8)
C9	0.0180 (9)	0.0207 (10)	0.0163 (9)	−0.0016 (8)	0.0009 (7)	0.0013 (7)
C10	0.0150 (9)	0.0180 (9)	0.0177 (8)	−0.0012 (7)	0.0011 (7)	0.0015 (7)
C11	0.0164 (9)	0.0186 (10)	0.0191 (9)	−0.0025 (7)	0.0010 (7)	−0.0015 (7)
C12	0.0140 (9)	0.0244 (10)	0.0178 (9)	−0.0021 (8)	0.0024 (7)	0.0024 (8)
C13	0.0187 (10)	0.0400 (13)	0.0190 (10)	−0.0028 (9)	0.0027 (8)	−0.0010 (9)
C14	0.0204 (11)	0.0530 (16)	0.0223 (11)	0.0053 (10)	0.0017 (8)	0.0125 (10)
C15	0.0246 (11)	0.0371 (13)	0.0341 (12)	0.0091 (10)	0.0077 (9)	0.0167 (10)
C16	0.0248 (11)	0.0234 (11)	0.0313 (11)	0.0036 (9)	0.0095 (9)	0.0064 (9)
C17	0.0150 (9)	0.0223 (10)	0.0209 (9)	−0.0006 (8)	0.0048 (7)	0.0044 (8)
C18	0.0182 (9)	0.0185 (9)	0.0215 (9)	−0.0037 (8)	0.0039 (8)	0.0010 (8)
C19	0.0142 (9)	0.0274 (11)	0.0191 (9)	−0.0038 (8)	0.0022 (7)	0.0016 (8)
C20	0.0128 (9)	0.0251 (10)	0.0197 (9)	−0.0036 (8)	0.0011 (7)	0.0011 (8)
C21	0.0188 (10)	0.0320 (12)	0.0189 (9)	−0.0050 (8)	0.0001 (8)	0.0042 (8)
C22	0.0212 (10)	0.0300 (12)	0.0288 (11)	−0.0023 (9)	0.0009 (9)	0.0075 (9)
C23	0.0208 (10)	0.0233 (11)	0.0374 (12)	−0.0034 (8)	0.0020 (9)	−0.0006 (9)
C24	0.0188 (10)	0.0297 (11)	0.0247 (10)	−0.0044 (9)	0.0005 (8)	−0.0030 (9)
C25	0.0161 (9)	0.0249 (10)	0.0194 (9)	−0.0039 (8)	0.0019 (7)	0.0018 (8)
C26	0.0177 (9)	0.0260 (11)	0.0198 (9)	−0.0037 (8)	0.0010 (8)	0.0005 (8)
C27	0.0194 (10)	0.0368 (13)	0.0293 (11)	0.0021 (9)	0.0066 (8)	0.0039 (10)

Geometric parameters (Å, º) top

Br1—C1	1.906 (2)	C11—H11A	0.9900
O1—C19	1.210 (2)	C11—H11B	0.9900
O2—C18	1.214 (2)	C12—C17	1.388 (3)
O3—C26	1.209 (2)	C12—C13	1.394 (3)
N1—C9	1.445 (3)	C13—C14	1.389 (3)
N1—C27	1.466 (3)	C13—H13A	0.9500
N1—C8	1.473 (3)	C14—C15	1.390 (4)
C1—C2	1.379 (3)	C14—H14A	0.9500
C1—C6	1.383 (3)	C15—C16	1.380 (3)
C2—C3	1.390 (3)	C15—H15A	0.9500
C2—H2A	0.9500	C16—C17	1.396 (3)
C3—C4	1.395 (3)	C16—H16A	0.9500
C3—H3A	0.9500	C17—C18	1.472 (3)
C4—C5	1.399 (3)	C19—C20	1.479 (3)
C4—C7	1.510 (3)	C20—C21	1.392 (3)
C5—C6	1.390 (3)	C20—C25	1.398 (3)
C5—H5A	0.9500	C21—C22	1.380 (3)
C6—H6A	0.9500	C21—H21A	0.9500
C7—C8	1.546 (3)	C22—C23	1.403 (3)
C7—C10	1.553 (3)	C22—H22A	0.9500
C7—H7A	1.0000	C23—C24	1.387 (3)
C8—H8A	0.9900	C23—H23A	0.9500
C8—H8B	0.9900	C24—C25	1.390 (3)
C9—C19	1.545 (3)	C24—H24A	0.9500
C9—C26	1.553 (3)	C25—C26	1.488 (3)
C9—C10	1.583 (3)	C27—H27A	0.9800
C10—C18	1.544 (3)	C27—H27B	0.9800
C10—C11	1.546 (3)	C27—H27C	0.9800
C11—C12	1.512 (3)

C9—N1—C27	116.69 (17)	C17—C12—C13	119.36 (19)
C9—N1—C8	107.46 (16)	C17—C12—C11	111.48 (16)
C27—N1—C8	114.35 (16)	C13—C12—C11	129.16 (19)
C2—C1—C6	121.85 (19)	C14—C13—C12	118.4 (2)
C2—C1—Br1	118.66 (16)	C14—C13—H13A	120.8
C6—C1—Br1	119.48 (15)	C12—C13—H13A	120.8
C1—C2—C3	118.85 (19)	C13—C14—C15	121.6 (2)
C1—C2—H2A	120.6	C13—C14—H14A	119.2
C3—C2—H2A	120.6	C15—C14—H14A	119.2
C2—C3—C4	121.30 (18)	C16—C15—C14	120.4 (2)
C2—C3—H3A	119.4	C16—C15—H15A	119.8
C4—C3—H3A	119.4	C14—C15—H15A	119.8
C3—C4—C5	118.01 (18)	C15—C16—C17	117.9 (2)
C3—C4—C7	122.69 (18)	C15—C16—H16A	121.1
C5—C4—C7	119.30 (18)	C17—C16—H16A	121.1
C6—C5—C4	121.49 (19)	C12—C17—C16	122.24 (19)
C6—C5—H5A	119.3	C12—C17—C18	109.19 (17)
C4—C5—H5A	119.3	C16—C17—C18	128.53 (19)
C1—C6—C5	118.46 (18)	O2—C18—C17	127.45 (19)
C1—C6—H6A	120.8	O2—C18—C10	125.27 (18)
C5—C6—H6A	120.8	C17—C18—C10	107.28 (16)
C4—C7—C8	115.99 (17)	O1—C19—C20	126.71 (18)
C4—C7—C10	114.55 (15)	O1—C19—C9	126.11 (19)
C8—C7—C10	104.92 (15)	C20—C19—C9	107.17 (16)
C4—C7—H7A	106.9	C21—C20—C25	120.93 (19)
C8—C7—H7A	106.9	C21—C20—C19	129.02 (18)
C10—C7—H7A	106.9	C25—C20—C19	110.05 (17)
N1—C8—C7	105.26 (15)	C22—C21—C20	118.20 (19)
N1—C8—H8A	110.7	C22—C21—H21A	120.9
C7—C8—H8A	110.7	C20—C21—H21A	120.9
N1—C8—H8B	110.7	C21—C22—C23	120.8 (2)
C7—C8—H8B	110.7	C21—C22—H22A	119.6
H8A—C8—H8B	108.8	C23—C22—H22A	119.6
N1—C9—C19	115.00 (16)	C24—C23—C22	121.3 (2)
N1—C9—C26	117.37 (16)	C24—C23—H23A	119.4
C19—C9—C26	101.32 (15)	C22—C23—H23A	119.4
N1—C9—C10	100.95 (15)	C23—C24—C25	117.79 (19)
C19—C9—C10	112.11 (15)	C23—C24—H24A	121.1
C26—C9—C10	110.47 (16)	C25—C24—H24A	121.1
C18—C10—C11	103.44 (15)	C24—C25—C20	120.99 (19)
C18—C10—C7	113.34 (16)	C24—C25—C26	129.75 (18)
C11—C10—C7	118.79 (16)	C20—C25—C26	109.26 (18)
C18—C10—C9	111.89 (15)	O3—C26—C25	126.98 (19)
C11—C10—C9	109.65 (15)	O3—C26—C9	125.77 (19)
C7—C10—C9	99.93 (14)	C25—C26—C9	107.22 (15)
C12—C11—C10	103.93 (16)	N1—C27—H27A	109.5
C12—C11—H11A	111.0	N1—C27—H27B	109.5
C10—C11—H11A	111.0	H27A—C27—H27B	109.5
C12—C11—H11B	111.0	N1—C27—H27C	109.5
C10—C11—H11B	111.0	H27A—C27—H27C	109.5
H11A—C11—H11B	109.0	H27B—C27—H27C	109.5

C6—C1—C2—C3	−2.2 (3)	C14—C15—C16—C17	−1.9 (3)
Br1—C1—C2—C3	177.23 (14)	C13—C12—C17—C16	0.6 (3)
C1—C2—C3—C4	0.5 (3)	C11—C12—C17—C16	−179.99 (19)
C2—C3—C4—C5	1.2 (3)	C13—C12—C17—C18	178.51 (18)
C2—C3—C4—C7	−179.53 (18)	C11—C12—C17—C18	−2.1 (2)
C3—C4—C5—C6	−1.2 (3)	C15—C16—C17—C12	1.2 (3)
C7—C4—C5—C6	179.50 (17)	C15—C16—C17—C18	−176.3 (2)
C2—C1—C6—C5	2.2 (3)	C12—C17—C18—O2	168.6 (2)
Br1—C1—C6—C5	−177.24 (14)	C16—C17—C18—O2	−13.7 (3)
C4—C5—C6—C1	−0.4 (3)	C12—C17—C18—C10	−11.8 (2)
C3—C4—C7—C8	40.8 (2)	C16—C17—C18—C10	165.9 (2)
C5—C4—C7—C8	−139.97 (18)	C11—C10—C18—O2	−160.17 (19)
C3—C4—C7—C10	−81.7 (2)	C7—C10—C18—O2	−30.2 (3)
C5—C4—C7—C10	97.5 (2)	C9—C10—C18—O2	81.9 (2)
C9—N1—C8—C7	−25.6 (2)	C11—C10—C18—C17	20.3 (2)
C27—N1—C8—C7	−156.81 (17)	C7—C10—C18—C17	150.23 (16)
C4—C7—C8—N1	−131.75 (17)	C9—C10—C18—C17	−97.69 (18)
C10—C7—C8—N1	−4.3 (2)	N1—C9—C19—O1	−29.7 (3)
C27—N1—C9—C19	−65.1 (2)	C26—C9—C19—O1	−157.37 (19)
C8—N1—C9—C19	164.97 (16)	C10—C9—C19—O1	84.8 (2)
C27—N1—C9—C26	53.9 (2)	N1—C9—C19—C20	149.06 (16)
C8—N1—C9—C26	−76.0 (2)	C26—C9—C19—C20	21.41 (19)
C27—N1—C9—C10	174.03 (16)	C10—C9—C19—C20	−96.38 (18)
C8—N1—C9—C10	44.09 (18)	O1—C19—C20—C21	−16.3 (3)
C4—C7—C10—C18	−83.5 (2)	C9—C19—C20—C21	164.93 (19)
C8—C7—C10—C18	148.17 (16)	O1—C19—C20—C25	163.7 (2)
C4—C7—C10—C11	38.2 (2)	C9—C19—C20—C25	−15.0 (2)
C8—C7—C10—C11	−90.1 (2)	C25—C20—C21—C22	−0.1 (3)
C4—C7—C10—C9	157.30 (16)	C19—C20—C21—C22	180.0 (2)
C8—C7—C10—C9	28.97 (18)	C20—C21—C22—C23	−1.0 (3)
N1—C9—C10—C18	−164.44 (15)	C21—C22—C23—C24	1.1 (3)
C19—C9—C10—C18	72.7 (2)	C22—C23—C24—C25	−0.1 (3)
C26—C9—C10—C18	−39.5 (2)	C23—C24—C25—C20	−1.0 (3)
N1—C9—C10—C11	81.38 (17)	C23—C24—C25—C26	178.8 (2)
C19—C9—C10—C11	−41.5 (2)	C21—C20—C25—C24	1.1 (3)
C26—C9—C10—C11	−153.72 (15)	C19—C20—C25—C24	−178.89 (18)
N1—C9—C10—C7	−44.19 (17)	C21—C20—C25—C26	−178.72 (18)
C19—C9—C10—C7	−167.09 (16)	C19—C20—C25—C26	1.3 (2)
C26—C9—C10—C7	80.71 (17)	C24—C25—C26—O3	14.7 (4)
C18—C10—C11—C12	−20.64 (19)	C20—C25—C26—O3	−165.4 (2)
C7—C10—C11—C12	−147.24 (17)	C24—C25—C26—C9	−166.9 (2)
C9—C10—C11—C12	98.86 (17)	C20—C25—C26—C9	13.0 (2)
C10—C11—C12—C17	14.9 (2)	N1—C9—C26—O3	31.6 (3)
C10—C11—C12—C13	−165.8 (2)	C19—C9—C26—O3	157.7 (2)
C17—C12—C13—C14	−1.7 (3)	C10—C9—C26—O3	−83.3 (2)
C11—C12—C13—C14	179.1 (2)	N1—C9—C26—C25	−146.80 (17)
C12—C13—C14—C15	0.9 (3)	C19—C9—C26—C25	−20.7 (2)
C13—C14—C15—C16	0.9 (3)	C10—C9—C26—C25	98.26 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O1	0.99	2.40	3.053 (2)	123
C15—H15A···O2ⁱ	0.95	2.44	3.163 (3)	133
C22—H22A···O3ⁱ	0.95	2.57	3.225 (3)	126

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₀BrNO₃
M_r	486.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.8392 (1), 21.5849 (5), 12.7823 (3)
β (°)	98.422 (1)
V (Å³)	2139.55 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.95
Crystal size (mm)	0.42 × 0.20 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.492, 0.788
No. of measured, independent and observed [I > 2σ(I)] reflections	18795, 6300, 4709
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.094, 1.02
No. of reflections	6300
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.72

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
C11—H11B···O1	0.99	2.40	3.053 (2)	123
C15—H15A···O2ⁱ	0.95	2.44	3.163 (3)	133
C22—H22A···O3ⁱ	0.95	2.57	3.225 (3)	126

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

ACW, MAA and RI thank the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti of Sains Malaysia, Penang. This work was funded through Research Grant No. RUC (1001/PSK/8620012). HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Kumar, R. R., Perumal, S., Senthilkumar, P., Yogeeswari, P. & Sriram, D. (2009). Eur. J. Med. Chem. 44, 3821–3829. PubMed Google Scholar
Maheswari, S. U., Balamurugan, K., Perumal, S., Yogeeswari, P. & Sriram, D. (2010). Bioorg Med Chem Lett. 20, 7278–7282. Web of Science CSD CrossRef CAS PubMed Google Scholar
Moraski, G. C., Markley, L. D., Hipskind, P. A., Boshoff, H., Cho, S., Franzblau, S. G. & Miller, M. J. (2011). Am. Chem. Soc. Med. Chem. Lett. 2, 466–470. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Trivedi, A. R., Bhuva, V. R., Dholariya, B. H., Dodiya, D. K., Kataria, V. B. & Shah, V. H. (2010). Bioorg. Med. Chem. Lett. 20, 6100–6102. Web of Science CrossRef CAS PubMed Google Scholar

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Volume 67| Part 11| November 2011| Page o3124

doi:10.1107/S1600536811044515

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4′-(4-Bromo­phen­yl)-1′-methyl­di­spiro­[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4′-(4-Bromophenyl)-1′-methyldispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione