4′-(4-Bromo­phen­yl)-1′-methyl­dispiro­[acenaphthyl­ene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione

Wei, A.C.; Ali, M.A.; Choon, T.S.; Arshad, S.; Razak, I.A.

doi:10.1107/S1600536812014213

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1340-o1341

doi:10.1107/S1600536812014213

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4′-(4-Bromophenyl)-1′-methyldispiro[acenaphthylene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione

Ang Chee Wei,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Suhana Arshad ^b and Ibrahim Abdul Razak ^b ^*‡

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 22 March 2012; accepted 2 April 2012; online 13 April 2012)

In the title compound, C₃₀H₂₂BrNO₂, the cyclopentane ring of the dihydroacenaphthylene group and the pyrrolidine ring are both in envelope conformations with the spiro C atom and N atom, respectively, as the flap atom. The cyclopentane ring of the indane group adopts a half-chair conformation. A weak intramolecular C—H⋯O hydrogen bond forms an S(8) ring motif. The naphthalene ring system of the dihydroacenaphthylene group forms dihedral angles of 41.76 (6) and 42.17 (6)° with the benzene ring of the bromophenyl group and the benzene ring of the indane group, respectively. The dihedral angle between the two benzene rings is 83.92 (7)°. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ac plane. Weak C—H⋯π interactions are also observed.

Related literature

For related structures, see: Wei, Ali, Ismail et al. (2011 ); Wei, Ali, Yoon et al. (2011 ); Wei, Ali, Choon et al. (2011 ). For ring conformations, see: Cremer & Pople (1975 ). 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 ).

Experimental

Crystal data

C₃₀H₂₂BrNO₂
M_r = 508.40
Monoclinic, P 2₁ /c
a = 8.6638 (1) Å
b = 19.9429 (2) Å
c = 13.5225 (1) Å
β = 94.937 (1)°
V = 2327.77 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.80 mm⁻¹
T = 100 K
0.42 × 0.19 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.522, T_max = 0.748
31742 measured reflections
9279 independent reflections
6879 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.085
S = 1.03
9279 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29A⋯O1	0.95	2.25	3.1110 (17)	151
C4—H4A⋯O2ⁱ	0.95	2.59	3.3743 (19)	140
C16—H16A⋯N1ⁱⁱ	0.95	2.50	3.4278 (19)	165
C26—H26A⋯O1ⁱⁱⁱ	0.95	2.43	3.2597 (18)	146
C5—H5A⋯Cg1^iv	0.95	2.71	3.3186 (15)	123
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z; (iv) x+1, y, z.

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/S1600536812014213/lh5443sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014213/lh5443Isup2.hkl

checkCIF report

Comment top

As part of our ongoing search to discover novel heterocyclic compounds with antitubercular activity (Wei, Ali, Ismail et al., 2011; Wei, Ali, Yoon et al., 2011), our group has determined the crystal structure of the title compound.

In the molecular structure (Fig 1), the cyclopentane ring within the dihydro-acenaphthylene moiety (C1/C2/C10–C12) [puckering parameters, Q= 0.0742 (15) Å and ϕ= 151.2 (11)°] and the pyrrolidine ring (N1/C12/C13/C22/C23) [puckering parameters, Q= 0.4112 (14) Å and ϕ= 185.8 (2)°] are both in envelope conformation (Cremer & Pople, 1975) with atom C12 and atom N1 at the flap, respectively. Meanwhile, the cyclopentane ring (C13–C15/C20/C21) within the dihydro-indene moiety is twisted about C13–C14 bond [puckering parameters, Q= 0.2467 (15) Å and ϕ= 189.1 (3)°], thereby adopting half-chair conformation. The bond lengths and angles are within normal ranges and comparable to those related structures (Wei, Ali, Ismail et al., 2011; Wei, Ali, Yoon et al., 2011; Wei, Ali, Choon et al., 2011). An intramolecular C29—H29A···O1 hydrogen bond (Table 1) forms an S(8) ring motif (Bernstein et al., 1995). The naphthalene ring system (C2-C11) of dihydro-acenaphthylene group forms dihedral angles of 41.76 (6) and 42.17 (6)° with the benzene ring (C24-C29) of the bromophenyl group and the benzene ring (C15-C20) of the dihydro-indene group. The dihedral angle between the two benzene rings (C24-C29/C15-C20) is 83.92 (7)°.

The crystal packing is shown in Fig. 2. Weak intermolecular C4—H4A···O2ⁱ, C16—H16A···N1ⁱⁱ and C26—H26A···O16ⁱⁱⁱ (Table 1) hydrogen bonds link molecules into a two-dimensional network parallel to ac-plane. The crystal structure is further stabilized by weak intermolecular C5—H5A···Cg1 (Table 1) interactions (Cg1 is the centroid of the C15–C20 ring).

Related literature top

For related structures, see: Wei, Ali, Ismail et al. (2011); Wei, Ali, Yoon et al. (2011); Wei, Ali, Choon et al. (2011). For ring conformations, see: Cremer & Pople (1975). 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).

Experimental top

A mixture of (E)-2-(4-bromobenzylidene)-2,3-dihydro-1H-indene-1- one (0.001 mol), acenaphthenequinone (0.001 mol) and sarcosine (0.002 mol) (1:1:2) were dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction as evident from TLC, the excess solvent was evaporated slowly and the product was separated and recrystallized from methanol to reveal 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 30% probability displacement ellipsoids and the atom-numbering scheme. The dashed line indicates a weak hydrogen bond.
	Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

4'-(4-Bromophenyl)-1'-methyldispiro[acenaphthylene-1,2'-pyrrolidine- 3',2''-indane]-2,1''(1H)-dione top

Crystal data top

C₃₀H₂₂BrNO₂	F(000) = 1040
M_r = 508.40	D_x = 1.451 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9857 reflections
a = 8.6638 (1) Å	θ = 2.5–33.4°
b = 19.9429 (2) Å	µ = 1.80 mm⁻¹
c = 13.5225 (1) Å	T = 100 K
β = 94.937 (1)°	Block, yellow
V = 2327.77 (4) Å³	0.42 × 0.19 × 0.17 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	9279 independent reflections
Radiation source: fine-focus sealed tube	6879 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 33.9°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→13
T_min = 0.522, T_max = 0.748	k = −29→31
31742 measured reflections	l = −19→21

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0334P)² + 1.002P] where P = (F_o² + 2F_c²)/3
9279 reflections	(Δ/σ)_max = 0.002
308 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₃₀H₂₂BrNO₂	V = 2327.77 (4) Å³
M_r = 508.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6638 (1) Å	µ = 1.80 mm⁻¹
b = 19.9429 (2) Å	T = 100 K
c = 13.5225 (1) Å	0.42 × 0.19 × 0.17 mm
β = 94.937 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	9279 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6879 reflections with I > 2σ(I)
T_min = 0.522, T_max = 0.748	R_int = 0.034
31742 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.03	Δρ_max = 0.46 e Å⁻³
9279 reflections	Δρ_min = −0.49 e Å⁻³
308 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 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	0.480071 (19)	0.521944 (7)	0.244244 (11)	0.02379 (5)
O1	1.13667 (12)	0.37057 (5)	0.06701 (8)	0.0181 (2)
O2	0.73424 (12)	0.23859 (5)	−0.19577 (7)	0.0196 (2)
N1	1.02645 (13)	0.34177 (6)	−0.14796 (8)	0.0147 (2)
C1	1.14407 (15)	0.31588 (7)	0.02741 (10)	0.0143 (2)
C2	1.25652 (15)	0.26231 (7)	0.05489 (10)	0.0149 (2)
C3	1.37067 (16)	0.25607 (7)	0.13200 (10)	0.0171 (3)
H3A	1.3852	0.2895	0.1820	0.020*
C4	1.46532 (17)	0.19825 (8)	0.13408 (11)	0.0199 (3)
H4A	1.5426	0.1923	0.1876	0.024*
C5	1.44836 (16)	0.15013 (7)	0.06027 (11)	0.0194 (3)
H5A	1.5149	0.1122	0.0638	0.023*
C6	1.33380 (16)	0.15627 (7)	−0.02048 (10)	0.0162 (3)
C7	1.30942 (17)	0.11341 (7)	−0.10429 (11)	0.0187 (3)
H7A	1.3706	0.0742	−0.1087	0.022*
C8	1.19717 (17)	0.12873 (7)	−0.17900 (11)	0.0193 (3)
H8A	1.1838	0.0999	−0.2350	0.023*
C9	1.10026 (17)	0.18618 (7)	−0.17541 (10)	0.0168 (3)
H9A	1.0238	0.1955	−0.2282	0.020*
C10	1.11894 (16)	0.22784 (6)	−0.09453 (10)	0.0143 (2)
C11	1.23720 (15)	0.21288 (7)	−0.01929 (10)	0.0147 (2)
C12	1.03831 (15)	0.29248 (7)	−0.06780 (10)	0.0135 (2)
C13	0.86380 (15)	0.28669 (6)	−0.04240 (10)	0.0129 (2)
C14	0.84775 (16)	0.25846 (7)	0.06297 (10)	0.0145 (2)
H14A	0.9399	0.2696	0.1084	0.017*
H14B	0.7543	0.2766	0.0908	0.017*
C15	0.83414 (15)	0.18367 (7)	0.04746 (10)	0.0142 (2)
C16	0.85513 (16)	0.13264 (7)	0.11705 (11)	0.0182 (3)
H16A	0.8831	0.1424	0.1850	0.022*
C17	0.83410 (18)	0.06670 (8)	0.08463 (12)	0.0222 (3)
H17A	0.8506	0.0311	0.1311	0.027*
C18	0.78920 (18)	0.05166 (7)	−0.01488 (12)	0.0229 (3)
H18A	0.7741	0.0063	−0.0350	0.027*
C19	0.76666 (17)	0.10280 (7)	−0.08419 (11)	0.0198 (3)
H19A	0.7348	0.0933	−0.1517	0.024*
C20	0.79213 (16)	0.16845 (7)	−0.05171 (10)	0.0152 (2)
C21	0.78710 (16)	0.23101 (7)	−0.11033 (10)	0.0150 (2)
C22	0.79283 (15)	0.35678 (7)	−0.07174 (10)	0.0142 (2)
H22A	0.7097	0.3489	−0.1265	0.017*
C23	0.92408 (16)	0.39505 (7)	−0.11737 (10)	0.0157 (2)
H23A	0.8830	0.4221	−0.1751	0.019*
H23B	0.9794	0.4250	−0.0678	0.019*
C24	0.71902 (15)	0.39472 (7)	0.00913 (10)	0.0148 (2)
C25	0.55805 (16)	0.39731 (7)	0.00765 (11)	0.0182 (3)
H25A	0.4969	0.3736	−0.0425	0.022*
C26	0.48464 (17)	0.43384 (7)	0.07808 (12)	0.0210 (3)
H26A	0.3748	0.4356	0.0758	0.025*
C27	0.57526 (17)	0.46743 (7)	0.15114 (11)	0.0176 (3)
C28	0.73546 (17)	0.46420 (7)	0.15679 (11)	0.0185 (3)
H28A	0.7960	0.4864	0.2088	0.022*
C29	0.80658 (16)	0.42809 (7)	0.08538 (11)	0.0181 (3)
H29A	0.9164	0.4261	0.0886	0.022*
C30	1.17364 (17)	0.36523 (7)	−0.18036 (11)	0.0200 (3)
H30A	1.2386	0.3266	−0.1936	0.030*
H30B	1.2269	0.3929	−0.1282	0.030*
H30C	1.1542	0.3919	−0.2410	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03158 (9)	0.01891 (7)	0.02255 (8)	0.00434 (6)	0.01203 (6)	0.00014 (6)
O1	0.0180 (5)	0.0160 (5)	0.0198 (5)	−0.0010 (4)	−0.0013 (4)	−0.0046 (4)
O2	0.0239 (5)	0.0195 (5)	0.0144 (5)	−0.0010 (4)	−0.0047 (4)	−0.0009 (4)
N1	0.0153 (5)	0.0139 (5)	0.0150 (5)	0.0004 (4)	0.0016 (4)	0.0022 (4)
C1	0.0133 (6)	0.0162 (6)	0.0134 (6)	−0.0021 (4)	0.0009 (5)	0.0006 (5)
C2	0.0141 (6)	0.0155 (6)	0.0151 (6)	−0.0003 (4)	0.0008 (5)	0.0011 (5)
C3	0.0164 (6)	0.0189 (6)	0.0156 (6)	−0.0007 (5)	−0.0010 (5)	0.0007 (5)
C4	0.0159 (6)	0.0247 (7)	0.0187 (7)	0.0014 (5)	−0.0017 (5)	0.0040 (6)
C5	0.0182 (6)	0.0193 (7)	0.0207 (7)	0.0039 (5)	0.0013 (5)	0.0044 (5)
C6	0.0166 (6)	0.0163 (6)	0.0160 (6)	0.0014 (5)	0.0024 (5)	0.0022 (5)
C7	0.0220 (7)	0.0150 (6)	0.0196 (7)	0.0039 (5)	0.0039 (5)	0.0002 (5)
C8	0.0249 (7)	0.0172 (6)	0.0160 (6)	0.0010 (5)	0.0030 (5)	−0.0018 (5)
C9	0.0202 (6)	0.0171 (6)	0.0129 (6)	0.0010 (5)	−0.0004 (5)	0.0001 (5)
C10	0.0155 (6)	0.0138 (6)	0.0136 (6)	−0.0005 (4)	0.0015 (5)	0.0008 (5)
C11	0.0145 (6)	0.0151 (6)	0.0146 (6)	−0.0005 (5)	0.0018 (5)	0.0013 (5)
C12	0.0134 (6)	0.0137 (6)	0.0131 (6)	−0.0004 (4)	−0.0009 (5)	−0.0005 (5)
C13	0.0139 (6)	0.0122 (5)	0.0122 (6)	−0.0004 (4)	−0.0005 (5)	−0.0004 (4)
C14	0.0172 (6)	0.0142 (6)	0.0118 (6)	−0.0015 (5)	−0.0002 (5)	−0.0001 (5)
C15	0.0137 (6)	0.0142 (6)	0.0146 (6)	−0.0012 (4)	0.0007 (5)	−0.0006 (5)
C16	0.0184 (6)	0.0188 (6)	0.0175 (6)	−0.0009 (5)	0.0008 (5)	0.0026 (5)
C17	0.0247 (7)	0.0170 (6)	0.0249 (7)	0.0011 (5)	0.0030 (6)	0.0049 (6)
C18	0.0281 (8)	0.0128 (6)	0.0282 (8)	−0.0017 (5)	0.0052 (6)	−0.0020 (6)
C19	0.0242 (7)	0.0164 (6)	0.0190 (7)	−0.0032 (5)	0.0033 (5)	−0.0037 (5)
C20	0.0163 (6)	0.0141 (6)	0.0150 (6)	−0.0020 (5)	0.0004 (5)	−0.0001 (5)
C21	0.0153 (6)	0.0147 (6)	0.0148 (6)	−0.0006 (4)	0.0005 (5)	−0.0016 (5)
C22	0.0156 (6)	0.0135 (6)	0.0130 (6)	0.0013 (4)	−0.0013 (5)	0.0000 (5)
C23	0.0193 (6)	0.0119 (6)	0.0157 (6)	0.0008 (5)	0.0006 (5)	0.0015 (5)
C24	0.0162 (6)	0.0120 (6)	0.0160 (6)	0.0009 (4)	0.0006 (5)	0.0016 (5)
C25	0.0171 (6)	0.0157 (6)	0.0214 (7)	−0.0022 (5)	−0.0003 (5)	−0.0016 (5)
C26	0.0171 (6)	0.0192 (7)	0.0273 (7)	−0.0010 (5)	0.0050 (6)	−0.0001 (6)
C27	0.0230 (7)	0.0130 (6)	0.0178 (6)	0.0017 (5)	0.0063 (5)	0.0022 (5)
C28	0.0225 (7)	0.0157 (6)	0.0171 (6)	0.0012 (5)	0.0006 (5)	−0.0013 (5)
C29	0.0173 (6)	0.0179 (6)	0.0189 (7)	0.0015 (5)	−0.0003 (5)	−0.0018 (5)
C30	0.0188 (6)	0.0200 (7)	0.0217 (7)	−0.0012 (5)	0.0044 (5)	0.0028 (6)

Geometric parameters (Å, º) top

Br1—C27	1.9043 (13)	C14—H14A	0.9900
O1—C1	1.2192 (16)	C14—H14B	0.9900
O2—C21	1.2151 (17)	C15—C16	1.3873 (19)
N1—C12	1.4604 (17)	C15—C20	1.3925 (19)
N1—C30	1.4606 (17)	C16—C17	1.393 (2)
N1—C23	1.4662 (17)	C16—H16A	0.9500
C1—C2	1.4718 (19)	C17—C18	1.401 (2)
C1—C12	1.5848 (19)	C17—H17A	0.9500
C2—C3	1.380 (2)	C18—C19	1.388 (2)
C2—C11	1.4061 (19)	C18—H18A	0.9500
C3—C4	1.414 (2)	C19—C20	1.3924 (19)
C3—H3A	0.9500	C19—H19A	0.9500
C4—C5	1.383 (2)	C20—C21	1.4769 (19)
C4—H4A	0.9500	C22—C24	1.5158 (18)
C5—C6	1.416 (2)	C22—C23	1.5418 (18)
C5—H5A	0.9500	C22—H22A	1.0000
C6—C11	1.4062 (19)	C23—H23A	0.9900
C6—C7	1.421 (2)	C23—H23B	0.9900
C7—C8	1.375 (2)	C24—C25	1.3941 (19)
C7—H7A	0.9500	C24—C29	1.395 (2)
C8—C9	1.424 (2)	C25—C26	1.395 (2)
C8—H8A	0.9500	C25—H25A	0.9500
C9—C10	1.3721 (19)	C26—C27	1.381 (2)
C9—H9A	0.9500	C26—H26A	0.9500
C10—C11	1.412 (2)	C27—C28	1.385 (2)
C10—C12	1.5244 (18)	C28—C29	1.3902 (19)
C12—C13	1.5831 (18)	C28—H28A	0.9500
C13—C14	1.5495 (18)	C29—H29A	0.9500
C13—C21	1.5533 (19)	C30—H30A	0.9800
C13—C22	1.5644 (18)	C30—H30B	0.9800
C14—C15	1.5093 (19)	C30—H30C	0.9800

C12—N1—C30	115.52 (11)	C20—C15—C14	111.10 (11)
C12—N1—C23	106.50 (10)	C15—C16—C17	118.23 (14)
C30—N1—C23	114.67 (11)	C15—C16—H16A	120.9
O1—C1—C2	126.66 (13)	C17—C16—H16A	120.9
O1—C1—C12	124.87 (12)	C16—C17—C18	121.49 (14)
C2—C1—C12	108.38 (11)	C16—C17—H17A	119.3
C3—C2—C11	120.63 (13)	C18—C17—H17A	119.3
C3—C2—C1	132.24 (13)	C19—C18—C17	120.20 (14)
C11—C2—C1	107.05 (12)	C19—C18—H18A	119.9
C2—C3—C4	117.74 (13)	C17—C18—H18A	119.9
C2—C3—H3A	121.1	C18—C19—C20	117.95 (14)
C4—C3—H3A	121.1	C18—C19—H19A	121.0
C5—C4—C3	121.74 (14)	C20—C19—H19A	121.0
C5—C4—H4A	119.1	C19—C20—C15	122.01 (13)
C3—C4—H4A	119.1	C19—C20—C21	128.94 (13)
C4—C5—C6	121.34 (13)	C15—C20—C21	109.02 (12)
C4—C5—H5A	119.3	O2—C21—C20	127.35 (13)
C6—C5—H5A	119.3	O2—C21—C13	125.48 (12)
C11—C6—C5	116.03 (13)	C20—C21—C13	107.17 (11)
C11—C6—C7	116.38 (13)	C24—C22—C23	114.40 (11)
C5—C6—C7	127.53 (13)	C24—C22—C13	116.36 (11)
C8—C7—C6	119.97 (13)	C23—C22—C13	104.86 (10)
C8—C7—H7A	120.0	C24—C22—H22A	106.9
C6—C7—H7A	120.0	C23—C22—H22A	106.9
C7—C8—C9	122.40 (13)	C13—C22—H22A	106.9
C7—C8—H8A	118.8	N1—C23—C22	103.83 (10)
C9—C8—H8A	118.8	N1—C23—H23A	111.0
C10—C9—C8	119.01 (13)	C22—C23—H23A	111.0
C10—C9—H9A	120.5	N1—C23—H23B	111.0
C8—C9—H9A	120.5	C22—C23—H23B	111.0
C9—C10—C11	118.35 (12)	H23A—C23—H23B	109.0
C9—C10—C12	132.54 (13)	C25—C24—C29	118.20 (12)
C11—C10—C12	109.07 (12)	C25—C24—C22	119.46 (13)
C2—C11—C6	122.45 (13)	C29—C24—C22	122.34 (12)
C2—C11—C10	113.59 (12)	C24—C25—C26	121.59 (14)
C6—C11—C10	123.85 (13)	C24—C25—H25A	119.2
N1—C12—C10	113.43 (10)	C26—C25—H25A	119.2
N1—C12—C13	101.69 (10)	C27—C26—C25	118.49 (13)
C10—C12—C13	117.09 (11)	C27—C26—H26A	120.8
N1—C12—C1	113.80 (11)	C25—C26—H26A	120.8
C10—C12—C1	101.36 (11)	C26—C27—C28	121.48 (13)
C13—C12—C1	109.96 (10)	C26—C27—Br1	119.86 (11)
C14—C13—C21	102.49 (10)	C28—C27—Br1	118.63 (11)
C14—C13—C22	119.57 (10)	C27—C28—C29	119.19 (14)
C21—C13—C22	110.48 (11)	C27—C28—H28A	120.4
C14—C13—C12	112.89 (11)	C29—C28—H28A	120.4
C21—C13—C12	106.97 (10)	C28—C29—C24	121.00 (13)
C22—C13—C12	103.99 (10)	C28—C29—H29A	119.5
C15—C14—C13	104.09 (10)	C24—C29—H29A	119.5
C15—C14—H14A	110.9	N1—C30—H30A	109.5
C13—C14—H14A	110.9	N1—C30—H30B	109.5
C15—C14—H14B	110.9	H30A—C30—H30B	109.5
C13—C14—H14B	110.9	N1—C30—H30C	109.5
H14A—C14—H14B	109.0	H30A—C30—H30C	109.5
C16—C15—C20	120.09 (13)	H30B—C30—H30C	109.5
C16—C15—C14	128.79 (12)

O1—C1—C2—C3	5.4 (2)	C10—C12—C13—C22	−152.10 (11)
C12—C1—C2—C3	−178.06 (14)	C1—C12—C13—C22	92.99 (12)
O1—C1—C2—C11	−171.24 (13)	C21—C13—C14—C15	23.95 (13)
C12—C1—C2—C11	5.34 (14)	C22—C13—C14—C15	146.48 (11)
C11—C2—C3—C4	−0.7 (2)	C12—C13—C14—C15	−90.76 (12)
C1—C2—C3—C4	−176.92 (13)	C13—C14—C15—C16	162.48 (13)
C2—C3—C4—C5	1.9 (2)	C13—C14—C15—C20	−18.65 (14)
C3—C4—C5—C6	−0.7 (2)	C20—C15—C16—C17	0.4 (2)
C4—C5—C6—C11	−1.6 (2)	C14—C15—C16—C17	179.22 (13)
C4—C5—C6—C7	175.66 (14)	C15—C16—C17—C18	−1.6 (2)
C11—C6—C7—C8	0.64 (19)	C16—C17—C18—C19	0.9 (2)
C5—C6—C7—C8	−176.58 (14)	C17—C18—C19—C20	0.9 (2)
C6—C7—C8—C9	−1.2 (2)	C18—C19—C20—C15	−2.0 (2)
C7—C8—C9—C10	−0.1 (2)	C18—C19—C20—C21	175.43 (14)
C8—C9—C10—C11	1.82 (19)	C16—C15—C20—C19	1.4 (2)
C8—C9—C10—C12	179.18 (13)	C14—C15—C20—C19	−177.59 (12)
C3—C2—C11—C6	−1.7 (2)	C16—C15—C20—C21	−176.52 (12)
C1—C2—C11—C6	175.40 (12)	C14—C15—C20—C21	4.50 (15)
C3—C2—C11—C10	−177.99 (12)	C19—C20—C21—O2	13.6 (2)
C1—C2—C11—C10	−0.91 (15)	C15—C20—C21—O2	−168.64 (14)
C5—C6—C11—C2	2.75 (19)	C19—C20—C21—C13	−166.02 (14)
C7—C6—C11—C2	−174.79 (12)	C15—C20—C21—C13	11.70 (14)
C5—C6—C11—C10	178.69 (12)	C14—C13—C21—O2	158.12 (13)
C7—C6—C11—C10	1.15 (19)	C22—C13—C21—O2	29.63 (18)
C9—C10—C11—C2	173.85 (12)	C12—C13—C21—O2	−82.93 (16)
C12—C10—C11—C2	−4.09 (15)	C14—C13—C21—C20	−22.21 (13)
C9—C10—C11—C6	−2.4 (2)	C22—C13—C21—C20	−150.69 (11)
C12—C10—C11—C6	179.65 (12)	C12—C13—C21—C20	96.74 (12)
C30—N1—C12—C10	−61.01 (15)	C14—C13—C22—C24	3.30 (17)
C23—N1—C12—C10	170.39 (11)	C21—C13—C22—C24	121.81 (12)
C30—N1—C12—C13	172.37 (11)	C12—C13—C22—C24	−123.73 (12)
C23—N1—C12—C13	43.77 (13)	C14—C13—C22—C23	130.78 (12)
C30—N1—C12—C1	54.18 (15)	C21—C13—C22—C23	−110.71 (12)
C23—N1—C12—C1	−74.42 (13)	C12—C13—C22—C23	3.75 (13)
C9—C10—C12—N1	−48.4 (2)	C12—N1—C23—C22	−42.08 (13)
C11—C10—C12—N1	129.14 (12)	C30—N1—C23—C22	−171.17 (11)
C9—C10—C12—C13	69.61 (19)	C24—C22—C23—N1	150.47 (11)
C11—C10—C12—C13	−112.85 (13)	C13—C22—C23—N1	21.81 (13)
C9—C10—C12—C1	−170.79 (14)	C23—C22—C24—C25	133.34 (13)
C11—C10—C12—C1	6.75 (13)	C13—C22—C24—C25	−104.04 (15)
O1—C1—C12—N1	47.22 (17)	C23—C22—C24—C29	−46.03 (18)
C2—C1—C12—N1	−129.43 (11)	C13—C22—C24—C29	76.59 (16)
O1—C1—C12—C10	169.35 (12)	C29—C24—C25—C26	2.0 (2)
C2—C1—C12—C10	−7.30 (13)	C22—C24—C25—C26	−177.35 (13)
O1—C1—C12—C13	−66.10 (16)	C24—C25—C26—C27	−0.7 (2)
C2—C1—C12—C13	117.25 (11)	C25—C26—C27—C28	−1.5 (2)
N1—C12—C13—C14	−159.00 (10)	C25—C26—C27—Br1	176.49 (11)
C10—C12—C13—C14	76.81 (14)	C26—C27—C28—C29	2.1 (2)
C1—C12—C13—C14	−38.09 (14)	Br1—C27—C28—C29	−175.86 (11)
N1—C12—C13—C21	89.02 (12)	C27—C28—C29—C24	−0.6 (2)
C10—C12—C13—C21	−35.17 (15)	C25—C24—C29—C28	−1.4 (2)
C1—C12—C13—C21	−150.08 (11)	C22—C24—C29—C28	178.00 (13)
N1—C12—C13—C22	−27.92 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29A···O1	0.95	2.25	3.1110 (17)	151
C4—H4A···O2ⁱ	0.95	2.59	3.3743 (19)	140
C16—H16A···N1ⁱⁱ	0.95	2.50	3.4278 (19)	165
C26—H26A···O1ⁱⁱⁱ	0.95	2.43	3.2597 (18)	146
C5—H5A···Cg1^iv	0.95	2.71	3.3186 (15)	123

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

Experimental details

Crystal data
Chemical formula	C₃₀H₂₂BrNO₂
M_r	508.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.6638 (1), 19.9429 (2), 13.5225 (1)
β (°)	94.937 (1)
V (Å³)	2327.77 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.80
Crystal size (mm)	0.42 × 0.19 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.522, 0.748
No. of measured, independent and observed [I > 2σ(I)] reflections	31742, 9279, 6879
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.784

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.085, 1.03
No. of reflections	9279
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.49

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 C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29A···O1	0.9500	2.2500	3.1110 (17)	151.00
C4—H4A···O2ⁱ	0.95	2.59	3.3743 (19)	140.4
C16—H16A···N1ⁱⁱ	0.95	2.50	3.4278 (19)	164.7
C26—H26A···O1ⁱⁱⁱ	0.9500	2.4300	3.2597 (18)	146.00
C5—H5A···Cg1^iv	0.9500	2.71	3.3186 (15)	123

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

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors wish to express their thank to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malysia, Penang, and the Malaysian Goverment for the Research University Grant No. 1001/PSK/8620012 and No.1001/PFIZIK/811151 and also providing research facilities.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. 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
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
Wei, A. C., Ali, M. A., Ismail, R., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o3124. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wei, A. C., Ali, M. A., Yoon, Y. K., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o3274. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Pages o1340-o1341

doi:10.1107/S1600536812014213

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

4′-(4-Bromo­phen­yl)-1′-methyl­di­spiro­[ace­naphthyl­ene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4′-(4-Bromophenyl)-1′-methyldispiro[acenaphthylene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione