4′-[5-(4-Fluoro­phen­yl)pyridin-3-yl]-1′-methyl­dispiro­[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

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

doi:10.1107/S1600536811032946

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages o2381-o2382

doi:10.1107/S1600536811032946

Open

access

4′-[5-(4-Fluorophenyl)pyridin-3-yl]-1′-methyldispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Ang Chee Wei,^a Mohamed Ashraf Ali,^a Rusli Ismail,^a Ching Kheng Quah ^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 12 August 2011; accepted 14 August 2011; online 27 August 2011)

In the title compound, C₃₂H₂₃FN₂O₃, the pyrrolidine ring adopts an envelope conformation. The monoketo- and diketo-substituted five-membered rings are in envelope and half-chair conformations, respectively. The molecular structure is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked via intermolecular C—H⋯N and C—H⋯O hydrogen bonds into a three-dimensional network. The crystal structure is further consolidated by C—H⋯π interactions.

Related literature

For general background to and the biological activity of the title compound, see: Chande et al. (2005 ); Prasanna et al. (2010 ); Karthikeyan et al. (2010 ); Dye (2002 ); Duncan & Barry (2004 ). For related structures, see: Kumar et al. (2010 ); Wei et al. (2011 ). For reference bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₃₂H₂₃FN₂O₃
M_r = 502.52
Monoclinic, P 2₁ /c
a = 14.8997 (2) Å
b = 7.7993 (1) Å
c = 23.0188 (3) Å
β = 112.638 (1)°
V = 2468.86 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.36 × 0.17 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.968, T_max = 0.996
27325 measured reflections
7184 independent reflections
4664 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.135
S = 0.99
7184 reflections
344 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N2/C22–C26 pyridyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯N2ⁱ	0.95	2.56	3.476 (2)	163
C13—H13A⋯N1ⁱⁱ	0.95	2.45	3.387 (2)	168
C15—H15A⋯O2ⁱⁱⁱ	0.95	2.44	3.381 (3)	169
C18—H18A⋯O2	0.99	2.40	3.077 (2)	125
C20—H20A⋯O3^iv	0.99	2.55	3.318 (2)	135
C4—H4A⋯Cg1^v	0.95	2.65	3.552 (2)	159
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536811032946/wn2449sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032946/wn2449Isup2.hkl

checkCIF report

Comment top

Spiro compounds have drawn considerable attention due to their antiseptic, analgesic and broad-spectrum antimicrobial activities (Chande et al., 2005). Many of these compounds are found to have comparable or even better antimycobacterial activities than some of the first-line TB drugs currently available (Prasanna et al., 2010; Karthikeyan et al., 2010). Tuberculosis (TB) is a chronic illness caused by Mycobacterium tuberculosis and kills approximately 2 million people each year (Dye, 2002). Thus there is an urgent need to develop potent new antitubercular agents with new mechanisms of action and low toxicity profiles which are effective against drug-susceptible and drug-resistant strains of M. tuberculosis (Duncan & Barry, 2004).

The molecular structure is shown in Fig. 1. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those in related crystal structures (Kumar et al., 2010; Wei et al., 2011).

The pyrrolidine ring (N1/C1/C10/C19/C20) adopts an envelope conformation, puckering parameters (Cremer & Pople, 1975) Q = 0.4855 (18) Å and ϕ = 41.8 (2)°, with atom C1 at the flap. The five-membered carbocyclic ring, C1-C3/C8/C9 is twisted on C9—C1, with puckering parameters Q = 0.1846 (18) Å and ϕ = 170.4 (6)°, thereby adopting a half-chair conformation. The five-membered carbocyclic ring, C10-C12/C17/C18 adopts an envelope conformation, with puckering parameters Q = 0.1277 (18) Å and ϕ = 359.4 (8)°, and with atom C10 at the flap.

If the six-membered rings N2/C22–C26, C3–C8, C12–C17 and C27–32 are denoted by R4, R5, R6, R7 then the dihedral angles for R4^R5, R5^R6, R4^R6 and R4^R7 are 69.10 (8), 39.95 (8), 78.82 (9) and 33.46 (9)°, respectively.

The molecular structure is stabilized by an intramolecular C18–H18A···O2 hydrogen bond (Table 1), which generates an S(6) ring motif (Fig. 1, Bernstein et al., 1995). In the crystal structure, Fig. 2, molecules are linked via intermolecular C6—H6A···N2, C13—H13A···N1, C15—H15A···O2 and C20—H20A···O3 hydrogen bonds (Table 1) into a three-dimensional network. The crystal structure is further consolidated by C4—H4A···Cg1 (Table 1) interactions, where Cg1 is the centroid of the N2/C22-C26 pyridyl ring.

Related literature top

For general background to and the biological activity of the title compound, see: Chande et al. (2005); Prasanna et al. (2010); Karthikeyan et al. (2010); Dye (2002); Duncan & Barry (2004). For related structures, see: Kumar et al. (2010); Wei et al. (2011). For reference bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For ring conformations, see: Cremer & Pople (1975).

Experimental top

A mixture of (E)-2-(5-(4-flurophenyl) pyridin-3-yl) methylene)-2, 3-dihydro-1H-indene-1-one (0.001 mmol), ninhydrin (0.001 mmol) and sarcosine (0.002 mmol) (1:1:2) was dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction, as evident from TLC, the mixture was poured into water (50 ml). The precipitated solid was filtered, washed with water and recrystallised from a pet. ether - ethyl acetate mixture (1:1) to yield the title compound as yellow crystals.

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 molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

4'-[5-(4-Fluorophenyl)pyridin-3-yl]-1'-methyldispiro[indan-2,2'-pyrrolidine- 3',2''-indan]-1,3,1''-trione top

Crystal data top

C₃₂H₂₃FN₂O₃	F(000) = 1048
M_r = 502.52	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5035 reflections
a = 14.8997 (2) Å	θ = 2.8–28.1°
b = 7.7993 (1) Å	µ = 0.09 mm⁻¹
c = 23.0188 (3) Å	T = 100 K
β = 112.638 (1)°	Plate, yellow
V = 2468.86 (6) Å³	0.36 × 0.17 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7184 independent reflections
Radiation source: fine-focus sealed tube	4664 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→20
T_min = 0.968, T_max = 0.996	k = −10→10
27325 measured reflections	l = −32→32

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0641P)²] where P = (F_o² + 2F_c²)/3
7184 reflections	(Δ/σ)_max = 0.001
344 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₃₂H₂₃FN₂O₃	V = 2468.86 (6) Å³
M_r = 502.52	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.8997 (2) Å	µ = 0.09 mm⁻¹
b = 7.7993 (1) Å	T = 100 K
c = 23.0188 (3) Å	0.36 × 0.17 × 0.05 mm
β = 112.638 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7184 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4664 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.996	R_int = 0.057
27325 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 0.99	Δρ_max = 0.29 e Å⁻³
7184 reflections	Δρ_min = −0.27 e Å⁻³
344 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
F1	−0.02526 (8)	0.88163 (14)	0.42880 (5)	0.0352 (3)
O1	0.53116 (8)	0.12559 (15)	0.85281 (6)	0.0203 (3)
O2	0.22158 (9)	0.20148 (15)	0.85535 (6)	0.0212 (3)
O3	0.38943 (8)	−0.17977 (14)	0.76020 (6)	0.0187 (3)
N1	0.35687 (10)	0.35355 (16)	0.80293 (6)	0.0142 (3)
N2	0.30185 (11)	0.07049 (18)	0.54724 (7)	0.0200 (3)
C1	0.35388 (12)	0.17247 (19)	0.81705 (7)	0.0133 (3)
C2	0.45362 (12)	0.08860 (19)	0.85599 (8)	0.0146 (3)
C3	0.43827 (12)	−0.03372 (19)	0.90018 (7)	0.0144 (3)
C4	0.50353 (13)	−0.1516 (2)	0.93975 (8)	0.0180 (4)
H4A	0.5677	−0.1626	0.9409	0.022*
C5	0.47110 (14)	−0.2526 (2)	0.97738 (8)	0.0206 (4)
H5A	0.5142	−0.3338	1.0050	0.025*
C6	0.37646 (14)	−0.2379 (2)	0.97576 (8)	0.0232 (4)
H6A	0.3560	−0.3103	1.0015	0.028*
C7	0.31210 (13)	−0.1179 (2)	0.93668 (8)	0.0202 (4)
H7A	0.2481	−0.1062	0.9357	0.024*
C8	0.34458 (12)	−0.0158 (2)	0.89913 (7)	0.0153 (3)
C9	0.29442 (12)	0.1276 (2)	0.85693 (8)	0.0158 (3)
C10	0.30739 (11)	0.09841 (19)	0.74827 (8)	0.0130 (3)
C11	0.31431 (12)	−0.09919 (19)	0.74843 (7)	0.0140 (3)
C12	0.21613 (12)	−0.1679 (2)	0.73393 (8)	0.0155 (3)
C13	0.18807 (12)	−0.3386 (2)	0.73650 (8)	0.0178 (4)
H13A	0.2347	−0.4285	0.7487	0.021*
C14	0.09024 (13)	−0.3714 (2)	0.72068 (9)	0.0224 (4)
H14A	0.0692	−0.4855	0.7225	0.027*
C15	0.02184 (13)	−0.2386 (2)	0.70207 (9)	0.0225 (4)
H15A	−0.0451	−0.2643	0.6909	0.027*
C16	0.05016 (12)	−0.0699 (2)	0.69970 (8)	0.0191 (4)
H16A	0.0033	0.0196	0.6867	0.023*
C17	0.14895 (12)	−0.0346 (2)	0.71677 (7)	0.0150 (3)
C18	0.19694 (11)	0.1362 (2)	0.71821 (8)	0.0155 (3)
H18A	0.1781	0.2198	0.7439	0.019*
H18B	0.1785	0.1826	0.6751	0.019*
C19	0.37211 (12)	0.19184 (19)	0.71845 (8)	0.0137 (3)
H19A	0.4335	0.1243	0.7297	0.016*
C20	0.39874 (12)	0.3643 (2)	0.75442 (8)	0.0156 (3)
H20A	0.4702	0.3790	0.7741	0.019*
H20B	0.3704	0.4618	0.7257	0.019*
C21	0.40153 (13)	0.4657 (2)	0.85715 (8)	0.0187 (4)
H21A	0.3638	0.4615	0.8838	0.028*
H21B	0.4026	0.5836	0.8427	0.028*
H21C	0.4682	0.4275	0.8814	0.028*
C22	0.32635 (12)	0.2035 (2)	0.64733 (8)	0.0150 (3)
C23	0.33944 (12)	0.0714 (2)	0.61049 (8)	0.0171 (3)
H23A	0.3775	−0.0243	0.6315	0.021*
C24	0.24663 (12)	0.2045 (2)	0.51798 (8)	0.0185 (4)
H24A	0.2200	0.2059	0.4733	0.022*
C25	0.22608 (12)	0.3425 (2)	0.54969 (8)	0.0157 (3)
C26	0.26802 (12)	0.3398 (2)	0.61536 (8)	0.0157 (3)
H26A	0.2566	0.4323	0.6385	0.019*
C27	0.16180 (12)	0.4862 (2)	0.51584 (8)	0.0170 (3)
C28	0.08191 (13)	0.4584 (2)	0.45942 (8)	0.0207 (4)
H28A	0.0704	0.3471	0.4412	0.025*
C29	0.01936 (13)	0.5917 (2)	0.42980 (9)	0.0247 (4)
H29A	−0.0349	0.5731	0.3915	0.030*
C30	0.03784 (13)	0.7509 (2)	0.45716 (9)	0.0246 (4)
C31	0.11572 (13)	0.7859 (2)	0.51189 (9)	0.0239 (4)
H31A	0.1265	0.8982	0.5292	0.029*
C32	0.17830 (13)	0.6522 (2)	0.54108 (8)	0.0210 (4)
H32A	0.2332	0.6735	0.5788	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0311 (7)	0.0361 (6)	0.0309 (7)	0.0124 (5)	0.0036 (5)	0.0117 (5)
O1	0.0139 (6)	0.0242 (6)	0.0226 (7)	0.0003 (5)	0.0068 (5)	0.0041 (5)
O2	0.0162 (6)	0.0261 (6)	0.0231 (7)	0.0044 (5)	0.0097 (5)	0.0004 (5)
O3	0.0148 (6)	0.0168 (6)	0.0249 (7)	0.0031 (5)	0.0082 (5)	0.0019 (5)
N1	0.0177 (7)	0.0118 (6)	0.0132 (7)	−0.0006 (5)	0.0060 (6)	0.0002 (5)
N2	0.0198 (8)	0.0215 (7)	0.0194 (8)	−0.0020 (6)	0.0083 (6)	−0.0038 (6)
C1	0.0131 (8)	0.0136 (7)	0.0130 (8)	0.0008 (6)	0.0049 (6)	0.0015 (6)
C2	0.0146 (8)	0.0132 (7)	0.0151 (8)	0.0009 (6)	0.0047 (6)	−0.0013 (6)
C3	0.0164 (8)	0.0138 (7)	0.0118 (7)	0.0004 (6)	0.0042 (6)	−0.0008 (6)
C4	0.0214 (9)	0.0162 (8)	0.0138 (8)	0.0022 (7)	0.0039 (7)	−0.0014 (6)
C5	0.0305 (10)	0.0135 (8)	0.0141 (8)	0.0027 (7)	0.0044 (7)	0.0019 (6)
C6	0.0372 (11)	0.0181 (8)	0.0165 (9)	−0.0046 (8)	0.0128 (8)	0.0015 (7)
C7	0.0230 (10)	0.0205 (8)	0.0199 (9)	−0.0025 (7)	0.0115 (7)	−0.0004 (7)
C8	0.0176 (8)	0.0154 (7)	0.0126 (8)	−0.0015 (6)	0.0056 (6)	−0.0019 (6)
C9	0.0136 (8)	0.0177 (8)	0.0158 (8)	−0.0008 (6)	0.0051 (7)	−0.0006 (6)
C10	0.0109 (8)	0.0131 (7)	0.0149 (8)	0.0008 (6)	0.0050 (6)	0.0010 (6)
C11	0.0152 (8)	0.0149 (7)	0.0118 (8)	0.0006 (6)	0.0051 (6)	0.0011 (6)
C12	0.0142 (8)	0.0163 (8)	0.0159 (8)	−0.0016 (6)	0.0059 (7)	−0.0009 (6)
C13	0.0186 (9)	0.0161 (8)	0.0197 (9)	−0.0007 (7)	0.0085 (7)	−0.0006 (7)
C14	0.0238 (10)	0.0186 (8)	0.0266 (10)	−0.0068 (7)	0.0118 (8)	−0.0024 (7)
C15	0.0152 (9)	0.0294 (9)	0.0233 (9)	−0.0054 (7)	0.0078 (7)	−0.0016 (7)
C16	0.0136 (8)	0.0244 (9)	0.0187 (8)	0.0008 (7)	0.0055 (7)	−0.0005 (7)
C17	0.0143 (8)	0.0179 (8)	0.0132 (8)	0.0001 (6)	0.0059 (6)	−0.0003 (6)
C18	0.0135 (8)	0.0157 (8)	0.0163 (8)	0.0019 (6)	0.0047 (6)	0.0024 (6)
C19	0.0122 (8)	0.0150 (7)	0.0147 (8)	−0.0001 (6)	0.0060 (6)	0.0006 (6)
C20	0.0177 (9)	0.0149 (7)	0.0138 (8)	−0.0027 (6)	0.0057 (7)	0.0010 (6)
C21	0.0203 (9)	0.0185 (8)	0.0150 (8)	−0.0016 (7)	0.0043 (7)	−0.0013 (6)
C22	0.0137 (8)	0.0179 (8)	0.0150 (8)	−0.0009 (6)	0.0072 (7)	0.0003 (6)
C23	0.0153 (9)	0.0182 (8)	0.0193 (9)	−0.0005 (7)	0.0082 (7)	−0.0012 (7)
C24	0.0171 (9)	0.0231 (8)	0.0152 (8)	−0.0044 (7)	0.0059 (7)	−0.0027 (7)
C25	0.0135 (8)	0.0183 (8)	0.0162 (8)	−0.0038 (6)	0.0066 (7)	0.0002 (6)
C26	0.0165 (8)	0.0157 (8)	0.0160 (8)	−0.0001 (6)	0.0074 (7)	−0.0013 (6)
C27	0.0150 (8)	0.0220 (8)	0.0149 (8)	−0.0016 (7)	0.0070 (7)	0.0020 (7)
C28	0.0191 (9)	0.0278 (9)	0.0149 (8)	−0.0007 (7)	0.0063 (7)	0.0001 (7)
C29	0.0187 (9)	0.0371 (10)	0.0157 (9)	0.0010 (8)	0.0039 (7)	0.0028 (8)
C30	0.0212 (10)	0.0280 (9)	0.0229 (10)	0.0075 (8)	0.0065 (8)	0.0117 (8)
C31	0.0223 (10)	0.0207 (9)	0.0270 (10)	0.0004 (7)	0.0075 (8)	0.0053 (7)
C32	0.0188 (9)	0.0225 (9)	0.0187 (9)	−0.0021 (7)	0.0038 (7)	0.0037 (7)

Geometric parameters (Å, º) top

F1—C30	1.3702 (19)	C15—C16	1.390 (2)
O1—C2	1.2200 (19)	C15—H15A	0.9500
O2—C9	1.2170 (19)	C16—C17	1.397 (2)
O3—C11	1.2196 (19)	C16—H16A	0.9500
N1—C1	1.4537 (19)	C17—C18	1.506 (2)
N1—C21	1.458 (2)	C18—H18A	0.9900
N1—C20	1.476 (2)	C18—H18B	0.9900
N2—C24	1.341 (2)	C19—C22	1.515 (2)
N2—C23	1.344 (2)	C19—C20	1.549 (2)
C1—C9	1.541 (2)	C19—H19A	1.0000
C1—C2	1.554 (2)	C20—H20A	0.9900
C1—C10	1.574 (2)	C20—H20B	0.9900
C2—C3	1.475 (2)	C21—H21A	0.9800
C3—C4	1.393 (2)	C21—H21B	0.9800
C3—C8	1.394 (2)	C21—H21C	0.9800
C4—C5	1.388 (2)	C22—C26	1.391 (2)
C4—H4A	0.9500	C22—C23	1.395 (2)
C5—C6	1.401 (3)	C23—H23A	0.9500
C5—H5A	0.9500	C24—C25	1.399 (2)
C6—C7	1.393 (2)	C24—H24A	0.9500
C6—H6A	0.9500	C25—C26	1.396 (2)
C7—C8	1.392 (2)	C25—C27	1.485 (2)
C7—H7A	0.9500	C26—H26A	0.9500
C8—C9	1.481 (2)	C27—C28	1.400 (2)
C10—C11	1.545 (2)	C27—C32	1.401 (2)
C10—C18	1.548 (2)	C28—C29	1.388 (2)
C10—C19	1.562 (2)	C28—H28A	0.9500
C11—C12	1.471 (2)	C29—C30	1.371 (3)
C12—C17	1.391 (2)	C29—H29A	0.9500
C12—C13	1.403 (2)	C30—C31	1.372 (3)
C13—C14	1.384 (2)	C31—C32	1.388 (2)
C13—H13A	0.9500	C31—H31A	0.9500
C14—C15	1.399 (2)	C32—H32A	0.9500
C14—H14A	0.9500

C1—N1—C21	115.76 (13)	C12—C17—C18	111.79 (14)
C1—N1—C20	106.41 (12)	C16—C17—C18	128.35 (15)
C21—N1—C20	115.26 (13)	C17—C18—C10	104.82 (12)
C24—N2—C23	117.35 (15)	C17—C18—H18A	110.8
N1—C1—C9	115.33 (13)	C10—C18—H18A	110.8
N1—C1—C2	115.67 (13)	C17—C18—H18B	110.8
C9—C1—C2	101.66 (12)	C10—C18—H18B	110.8
N1—C1—C10	99.85 (12)	H18A—C18—H18B	108.9
C9—C1—C10	112.61 (13)	C22—C19—C20	116.22 (13)
C2—C1—C10	112.26 (12)	C22—C19—C10	113.93 (13)
O1—C2—C3	126.58 (15)	C20—C19—C10	104.16 (13)
O1—C2—C1	125.69 (15)	C22—C19—H19A	107.4
C3—C2—C1	107.60 (13)	C20—C19—H19A	107.4
C4—C3—C8	121.34 (15)	C10—C19—H19A	107.4
C4—C3—C2	128.58 (16)	N1—C20—C19	105.02 (12)
C8—C3—C2	110.06 (14)	N1—C20—H20A	110.7
C5—C4—C3	117.37 (17)	C19—C20—H20A	110.7
C5—C4—H4A	121.3	N1—C20—H20B	110.7
C3—C4—H4A	121.3	C19—C20—H20B	110.7
C4—C5—C6	121.71 (16)	H20A—C20—H20B	108.8
C4—C5—H5A	119.1	N1—C21—H21A	109.5
C6—C5—H5A	119.1	N1—C21—H21B	109.5
C7—C6—C5	120.53 (16)	H21A—C21—H21B	109.5
C7—C6—H6A	119.7	N1—C21—H21C	109.5
C5—C6—H6A	119.7	H21A—C21—H21C	109.5
C8—C7—C6	117.91 (16)	H21B—C21—H21C	109.5
C8—C7—H7A	121.0	C26—C22—C23	116.61 (15)
C6—C7—H7A	121.0	C26—C22—C19	123.18 (14)
C7—C8—C3	121.11 (15)	C23—C22—C19	120.18 (14)
C7—C8—C9	129.14 (16)	N2—C23—C22	124.41 (16)
C3—C8—C9	109.66 (14)	N2—C23—H23A	117.8
O2—C9—C8	126.60 (15)	C22—C23—H23A	117.8
O2—C9—C1	125.80 (15)	N2—C24—C25	123.58 (16)
C8—C9—C1	107.55 (13)	N2—C24—H24A	118.2
C11—C10—C18	104.44 (12)	C25—C24—H24A	118.2
C11—C10—C19	114.49 (13)	C26—C25—C24	117.20 (15)
C18—C10—C19	116.40 (13)	C26—C25—C27	120.58 (15)
C11—C10—C1	111.14 (13)	C24—C25—C27	122.22 (15)
C18—C10—C1	111.13 (13)	C22—C26—C25	120.82 (15)
C19—C10—C1	99.42 (12)	C22—C26—H26A	119.6
O3—C11—C12	127.60 (15)	C25—C26—H26A	119.6
O3—C11—C10	124.71 (15)	C28—C27—C32	118.59 (16)
C12—C11—C10	107.67 (13)	C28—C27—C25	121.06 (15)
C17—C12—C13	121.85 (15)	C32—C27—C25	120.32 (15)
C17—C12—C11	109.63 (14)	C29—C28—C27	120.67 (17)
C13—C12—C11	128.51 (15)	C29—C28—H28A	119.7
C14—C13—C12	117.71 (16)	C27—C28—H28A	119.7
C14—C13—H13A	121.1	C30—C29—C28	118.33 (17)
C12—C13—H13A	121.1	C30—C29—H29A	120.8
C13—C14—C15	120.88 (16)	C28—C29—H29A	120.8
C13—C14—H14A	119.6	F1—C30—C29	118.38 (16)
C15—C14—H14A	119.6	F1—C30—C31	118.15 (17)
C16—C15—C14	121.10 (16)	C29—C30—C31	123.47 (17)
C16—C15—H15A	119.5	C30—C31—C32	117.89 (17)
C14—C15—H15A	119.5	C30—C31—H31A	121.1
C15—C16—C17	118.59 (16)	C32—C31—H31A	121.1
C15—C16—H16A	120.7	C31—C32—C27	121.03 (17)
C17—C16—H16A	120.7	C31—C32—H32A	119.5
C12—C17—C16	119.84 (15)	C27—C32—H32A	119.5

C21—N1—C1—C9	62.03 (19)	C10—C11—C12—C13	−171.27 (16)
C20—N1—C1—C9	−168.47 (13)	C17—C12—C13—C14	0.6 (3)
C21—N1—C1—C2	−56.37 (19)	C11—C12—C13—C14	179.77 (16)
C20—N1—C1—C2	73.13 (16)	C12—C13—C14—C15	0.8 (3)
C21—N1—C1—C10	−177.04 (13)	C13—C14—C15—C16	−0.8 (3)
C20—N1—C1—C10	−47.54 (15)	C14—C15—C16—C17	−0.4 (3)
N1—C1—C2—O1	−34.0 (2)	C13—C12—C17—C16	−1.9 (3)
C9—C1—C2—O1	−159.71 (16)	C11—C12—C17—C16	178.80 (15)
C10—C1—C2—O1	79.72 (19)	C13—C12—C17—C18	179.42 (15)
N1—C1—C2—C3	142.07 (13)	C11—C12—C17—C18	0.13 (19)
C9—C1—C2—C3	16.34 (16)	C15—C16—C17—C12	1.8 (2)
C10—C1—C2—C3	−104.23 (15)	C15—C16—C17—C18	−179.80 (16)
O1—C2—C3—C4	−11.5 (3)	C12—C17—C18—C10	−8.03 (18)
C1—C2—C3—C4	172.51 (15)	C16—C17—C18—C10	173.44 (16)
O1—C2—C3—C8	167.33 (16)	C11—C10—C18—C17	12.09 (16)
C1—C2—C3—C8	−8.67 (18)	C19—C10—C18—C17	139.37 (14)
C8—C3—C4—C5	1.0 (2)	C1—C10—C18—C17	−107.82 (14)
C2—C3—C4—C5	179.71 (16)	C11—C10—C19—C22	82.84 (17)
C3—C4—C5—C6	0.3 (2)	C18—C10—C19—C22	−39.30 (19)
C4—C5—C6—C7	−1.2 (3)	C1—C10—C19—C22	−158.66 (13)
C5—C6—C7—C8	0.8 (3)	C11—C10—C19—C20	−149.54 (13)
C6—C7—C8—C3	0.5 (2)	C18—C10—C19—C20	88.32 (16)
C6—C7—C8—C9	−175.63 (16)	C1—C10—C19—C20	−31.03 (14)
C4—C3—C8—C7	−1.4 (2)	C1—N1—C20—C19	27.63 (16)
C2—C3—C8—C7	179.65 (15)	C21—N1—C20—C19	157.41 (13)
C4—C3—C8—C9	175.39 (14)	C22—C19—C20—N1	130.35 (14)
C2—C3—C8—C9	−3.53 (18)	C10—C19—C20—N1	4.16 (16)
C7—C8—C9—O2	13.4 (3)	C20—C19—C22—C26	−31.0 (2)
C3—C8—C9—O2	−163.05 (16)	C10—C19—C22—C26	90.10 (18)
C7—C8—C9—C1	−169.08 (16)	C20—C19—C22—C23	150.83 (15)
C3—C8—C9—C1	14.43 (18)	C10—C19—C22—C23	−88.05 (18)
N1—C1—C9—O2	33.2 (2)	C24—N2—C23—C22	−1.3 (2)
C2—C1—C9—O2	159.15 (16)	C26—C22—C23—N2	1.8 (2)
C10—C1—C9—O2	−80.52 (19)	C19—C22—C23—N2	−179.93 (15)
N1—C1—C9—C8	−144.31 (14)	C23—N2—C24—C25	−0.5 (2)
C2—C1—C9—C8	−18.35 (16)	N2—C24—C25—C26	1.6 (2)
C10—C1—C9—C8	101.97 (15)	N2—C24—C25—C27	−177.84 (15)
N1—C1—C10—C11	168.49 (13)	C23—C22—C26—C25	−0.5 (2)
C9—C1—C10—C11	−68.64 (16)	C19—C22—C26—C25	−178.74 (15)
C2—C1—C10—C11	45.39 (17)	C24—C25—C26—C22	−1.0 (2)
N1—C1—C10—C18	−75.66 (15)	C27—C25—C26—C22	178.41 (15)
C9—C1—C10—C18	47.21 (17)	C26—C25—C27—C28	−145.25 (17)
C2—C1—C10—C18	161.23 (13)	C24—C25—C27—C28	34.2 (2)
N1—C1—C10—C19	47.52 (14)	C26—C25—C27—C32	32.6 (2)
C9—C1—C10—C19	170.39 (12)	C24—C25—C27—C32	−147.97 (17)
C2—C1—C10—C19	−75.59 (14)	C32—C27—C28—C29	−1.2 (3)
C18—C10—C11—O3	169.18 (15)	C25—C27—C28—C29	176.67 (16)
C19—C10—C11—O3	40.7 (2)	C27—C28—C29—C30	0.0 (3)
C1—C10—C11—O3	−70.9 (2)	C28—C29—C30—F1	−178.37 (16)
C18—C10—C11—C12	−12.43 (17)	C28—C29—C30—C31	0.9 (3)
C19—C10—C11—C12	−140.87 (14)	F1—C30—C31—C32	178.73 (16)
C1—C10—C11—C12	107.48 (15)	C29—C30—C31—C32	−0.6 (3)
O3—C11—C12—C17	−173.71 (16)	C30—C31—C32—C27	−0.7 (3)
C10—C11—C12—C17	7.96 (18)	C28—C27—C32—C31	1.6 (3)
O3—C11—C12—C13	7.1 (3)	C25—C27—C32—C31	−176.31 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N2/C22–C26 pyridyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···N2ⁱ	0.95	2.56	3.476 (2)	163
C13—H13A···N1ⁱⁱ	0.95	2.45	3.387 (2)	168
C15—H15A···O2ⁱⁱⁱ	0.95	2.44	3.381 (3)	169
C18—H18A···O2	0.99	2.40	3.077 (2)	125
C20—H20A···O3^iv	0.99	2.55	3.318 (2)	135
C4—H4A···Cg1^v	0.95	2.65	3.552 (2)	159

Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) x, y−1, z; (iii) −x, y−1/2, −z+3/2; (iv) −x+1, y+1/2, −z+3/2; (v) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₃₂H₂₃FN₂O₃
M_r	502.52
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.8997 (2), 7.7993 (1), 23.0188 (3)
β (°)	112.638 (1)
V (Å³)	2468.86 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.17 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.968, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	27325, 7184, 4664
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.135, 0.99
No. of reflections	7184
No. of parameters	344
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.27

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N2/C22–C26 pyridyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···N2ⁱ	0.95	2.56	3.476 (2)	163
C13—H13A···N1ⁱⁱ	0.95	2.45	3.387 (2)	168
C15—H15A···O2ⁱⁱⁱ	0.95	2.44	3.381 (3)	169
C18—H18A···O2	0.99	2.40	3.077 (2)	125
C20—H20A···O3^iv	0.99	2.55	3.318 (2)	135
C4—H4A···Cg1^v	0.95	2.65	3.552 (2)	159

Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) x, y−1, z; (iii) −x, y−1/2, −z+3/2; (iv) −x+1, y+1/2, −z+3/2; (v) −x+1, y−1/2, −z+3/2.

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for providing research facilities. HKF and CKQ also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chande, M. S., Verma, R. S., Barve, P. A. & Khanwelkar, R. R. (2005). Eur. J. Med. Chem. 40, 1143–1148. Web of Science CrossRef PubMed CAS 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
Duncan, K. & Barry, C. E. (2004). Curr Opin Microbiol. 7, 460–465. CrossRef CAS Google Scholar
Dye, C. (2002). Program of the 4th World Congress on Tuberculosis, Washington DC, USA, June 3–5. Google Scholar
Karthikeyan, S. V., Devi Bala, B., Alex Raja, V. P., Perumal, S., Yogeeswari, P. & Sriram, D. (2010). Bioorg. Med. Chem. Lett. 20, 350–353. CrossRef CAS Google Scholar
Kumar, R. S., Osman, H., Ali, M. A., Quah, C. K. & Fun, H.-K. (2010). Acta Cryst. E66, o1540–o1541. Web of Science CSD CrossRef IUCr Journals Google Scholar
Prasanna, P., Balamurugan, K., Perumal, S. & Yogeeswari, P. (2010). Eur. J. Med. Chem. 45, 5653–5661. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wei, A. C., Ali, M. A., Choon, T. S., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2383. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages o2381-o2382

doi:10.1107/S1600536811032946

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

4′-[5-(4-Fluoro­phen­yl)pyridin-3-yl]-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′-[5-(4-Fluorophenyl)pyridin-3-yl]-1′-methyldispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione