(4S)-4-(3,4-Dichloro­phen­yl)-1′-methyl-4′-phenyl-3,4-dihydronaphthalene-2-spiro-3′-pyrrolidine-2′-spiro-1′′-acenaphthyl­ene-1,2′′(2H,1′′H)-dione

Murugan, R.; Gunasekaran, B.; Narayanan, S.S.; Manivannan, V.

doi:10.1107/S1600536808013846

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1089

doi:10.1107/S1600536808013846

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(4S)-4-(3,4-Dichlorophenyl)-1′-methyl-4′-phenyl-3,4-dihydronaphthalene-2-spiro-3′-pyrrolidine-2′-spiro-1′′-acenaphthylene-1,2′′(2H,1′′H)-dione

R. Murugan,^a B. Gunasekaran,^b S. Sriman Narayanan ^a and V. Manivannan ^c ^*

^aDepartment of Analytical Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^bDepartment of Physics, AMET University, Kanathur, Chennai, India, and ^cDepartment of Physics, St. Peter's Engineering College, Avadi, Chennai, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 7 May 2008; accepted 8 May 2008; online 17 May 2008)

In the title compound, C₃₇H₂₇Cl₂NO₂, the 3,4-dichlorophenyl ring makes a dihedral angle of 46.66 (6)° with the phenyl ring. The molecular structure is stabilized by weak intramolecular C—H⋯O interactions and the crystal structure is stabilized by weak intermolecular C—H⋯O interactions. The C–C–C–C–C five-membered ring is planar, while the C–C–C–C–N five-membered ring adopts a half-chair conformation.

Related literature

For related lituerature, see: Sarala et al. (2006 ); Ramesh et al. (2007 ); Welch et al. (1984 ).

Experimental

Crystal data

C₃₇H₂₇Cl₂NO₂
M_r = 588.50
Monoclinic, C 2/c
a = 39.6142 (12) Å
b = 8.3031 (2) Å
c = 18.1810 (5) Å
β = 101.135 (3)°
V = 5867.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 (2) K
0.3 × 0.2 × 0.2 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.976, T_max = 0.979
67467 measured reflections
8160 independent reflections
5776 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.152
S = 1.06
8160 reflections
380 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2	0.97	2.49	3.045 (2)	116
C17—H17⋯O1	0.98	2.33	2.794 (2)	108
C32—H32⋯O2ⁱ	0.93	2.48	3.351 (3)	156
Symmetry code: (i) $[x, -y, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013846/bt2710sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013846/bt2710Isup2.hkl

checkCIF report

Comment top

The title compound acts in the central nervous system as a serotonine uptake inhibitor. Another similar compound sertraline hydrochloride is a very effective antidepressant. It selectively blocks serotonine re-uptake and is used for the treatment of depression, as well as dependency and other anxiety-related disorders (Welch et al., 1984).

The geometric parameters in the title compound agree with the reported values of a similar structure (Sarala et al., 2006; Ramesh et al., 2007). The 3,4-dichlorophenyl ring makes a dihedral angle of 46.66 (6) ° with the 4-phenyl ring. The 3,4-dihydro-1(2H)-naphthalenone ring adopts half-chair conformation [torsion angles: C(7)—C(16)—C(11)—C(10) -3.61 (3) °, and C(7)—C(8)—C(9)—C(10) -58.20 (17) °].

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular C—H···O interactions.

Related literature top

For related lituerature, see: Sarala et al. (2006); Ramesh et al. (2007); Welch et al. (1984).

Experimental top

1.0 mol of (E) -2-benzylidene-4-(3,4-dichlorophenyl)-3,4-dihydronaphthale-1 (2H)-one (1.0 g), 1.0 mol of acenaphthaquinoline (0.65 g) and 1.0 mol of sarcosine was refluxed in 10 ml of methanol for about 5.0 hrs. The solvent was removedand the crude solid was recrystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

(4S)-4-(3,4-Dichlorophenyl)-1'-methyl-4'-phenyl-3,4-dihydro- naphthalene-2-spiro-3'-pyrrolidine-2'-spiro-1''-acenaphthylene-1,2''(2H,1''H)- dione top

Crystal data top

C₃₇H₂₇Cl₂NO₂	F(000) = 2448
M_r = 588.50	D_x = 1.332 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 39.6142 (12) Å	θ = 2.0–25.5°
b = 8.3031 (2) Å	µ = 0.26 mm⁻¹
c = 18.1810 (5) Å	T = 293 K
β = 101.135 (3)°	Block, pale yellow
V = 5867.5 (3) Å³	0.3 × 0.2 × 0.2 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	8160 independent reflections
Radiation source: fine-focus sealed tube	5776 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 29.6°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −54→54
T_min = 0.976, T_max = 0.979	k = −11→11
67467 measured reflections	l = −25→25

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0658P)² + 5.0424P] where P = (F_o² + 2F_c²)/3
8160 reflections	(Δ/σ)_max < 0.001
380 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₃₇H₂₇Cl₂NO₂	V = 5867.5 (3) Å³
M_r = 588.50	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 39.6142 (12) Å	µ = 0.26 mm⁻¹
b = 8.3031 (2) Å	T = 293 K
c = 18.1810 (5) Å	0.3 × 0.2 × 0.2 mm
β = 101.135 (3)°

Data collection top

Bruker APEXII CCD diffractometer	8160 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5776 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.979	R_int = 0.033
67467 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.06	Δρ_max = 0.47 e Å⁻³
8160 reflections	Δρ_min = −0.32 e Å⁻³
380 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
Cl1	−0.002080 (13)	0.34019 (9)	0.38789 (4)	0.06938 (19)
Cl2	−0.014144 (16)	0.71550 (10)	0.36697 (4)	0.0841 (2)
O1	−0.19815 (3)	0.41995 (17)	0.58966 (8)	0.0475 (3)
O2	−0.12583 (4)	−0.06851 (17)	0.48514 (7)	0.0512 (3)
C9	−0.16950 (4)	0.23492 (18)	0.52002 (8)	0.0299 (3)
C10	−0.17115 (4)	0.36502 (19)	0.57873 (9)	0.0333 (3)
C25	−0.16332 (4)	0.06301 (19)	0.56048 (9)	0.0333 (3)
C17	−0.20508 (4)	0.2125 (2)	0.46665 (9)	0.0346 (3)
H17	−0.2226	0.2408	0.4959	0.042*
C1	−0.08342 (4)	0.4158 (2)	0.48236 (9)	0.0357 (3)
C7	−0.10569 (4)	0.3176 (2)	0.52492 (9)	0.0355 (3)
H7	−0.0949	0.2116	0.5348	0.043*
N1	−0.19450 (4)	−0.02695 (18)	0.52975 (9)	0.0425 (3)
C6	−0.08905 (5)	0.5788 (2)	0.47013 (11)	0.0469 (4)
H6	−0.1074	0.6281	0.4862	0.056*
C8	−0.14162 (4)	0.2907 (2)	0.47710 (9)	0.0336 (3)
H8A	−0.1398	0.2109	0.4391	0.040*
H8B	−0.1492	0.3905	0.4514	0.040*
C18	−0.21192 (4)	0.3169 (2)	0.39763 (9)	0.0381 (4)
C26	−0.12974 (4)	−0.0201 (2)	0.54571 (10)	0.0383 (4)
C2	−0.05649 (4)	0.3440 (2)	0.45610 (9)	0.0388 (4)
H2	−0.0526	0.2341	0.4630	0.047*
C3	−0.03528 (4)	0.4344 (3)	0.41954 (10)	0.0434 (4)
C11	−0.13780 (4)	0.4193 (2)	0.62382 (9)	0.0365 (3)
C16	−0.10692 (4)	0.3935 (2)	0.59997 (9)	0.0385 (4)
C35	−0.15689 (5)	0.0661 (2)	0.64538 (9)	0.0398 (4)
C36	−0.12327 (5)	0.0156 (2)	0.67380 (10)	0.0442 (4)
C24	−0.20754 (5)	0.0320 (2)	0.45465 (11)	0.0432 (4)
H24A	−0.2311	−0.0019	0.4366	0.052*
H24B	−0.1934	−0.0037	0.4198	0.052*
C27	−0.10569 (5)	−0.0354 (2)	0.61808 (11)	0.0454 (4)
C4	−0.04084 (5)	0.5976 (3)	0.40924 (11)	0.0494 (5)
C23	−0.20506 (5)	0.2687 (3)	0.32921 (11)	0.0517 (5)
H23	−0.1958	0.1672	0.3246	0.062*
C5	−0.06793 (5)	0.6693 (3)	0.43455 (12)	0.0529 (5)
H5	−0.0719	0.7792	0.4275	0.063*
C15	−0.07627 (5)	0.4379 (3)	0.64733 (11)	0.0572 (5)
H15	−0.0554	0.4209	0.6322	0.069*
C19	−0.22596 (5)	0.4685 (3)	0.40187 (13)	0.0539 (5)
H19	−0.2313	0.5030	0.4469	0.065*
C12	−0.13751 (6)	0.4898 (3)	0.69397 (11)	0.0521 (5)
H12	−0.1581	0.5081	0.7098	0.062*
C31	−0.10852 (7)	0.0127 (3)	0.75047 (12)	0.0620 (6)
C34	−0.17765 (6)	0.1082 (2)	0.69419 (11)	0.0532 (5)
H34	−0.2005	0.1372	0.6770	0.064*
C22	−0.21188 (6)	0.3698 (3)	0.26740 (12)	0.0648 (6)
H22	−0.2073	0.3351	0.2217	0.078*
C14	−0.07653 (7)	0.5065 (4)	0.71610 (12)	0.0726 (7)
H14	−0.0559	0.5357	0.7470	0.087*
C37	−0.19281 (6)	−0.2006 (2)	0.53935 (14)	0.0607 (6)
H37A	−0.2155	−0.2451	0.5263	0.091*
H37B	−0.1832	−0.2258	0.5907	0.091*
H37C	−0.1786	−0.2457	0.5074	0.091*
C13	−0.10704 (7)	0.5319 (3)	0.73924 (12)	0.0696 (7)
H13	−0.1070	0.5779	0.7859	0.083*
C28	−0.07225 (6)	−0.0877 (3)	0.63682 (15)	0.0686 (6)
H28	−0.0603	−0.1229	0.6006	0.082*
C32	−0.13034 (9)	0.0616 (3)	0.79920 (12)	0.0757 (8)
H32	−0.1220	0.0632	0.8507	0.091*
C21	−0.22524 (6)	0.5203 (4)	0.27320 (15)	0.0713 (7)
H21	−0.2296	0.5883	0.2318	0.086*
C20	−0.23216 (7)	0.5694 (3)	0.34039 (16)	0.0728 (7)
H20	−0.2411	0.6717	0.3448	0.087*
C33	−0.16333 (8)	0.1062 (3)	0.77166 (13)	0.0709 (7)
H33	−0.1771	0.1369	0.8053	0.085*
C30	−0.07403 (8)	−0.0392 (4)	0.76769 (16)	0.0849 (9)
H30	−0.0627	−0.0418	0.8175	0.102*
C29	−0.05687 (8)	−0.0856 (4)	0.71354 (19)	0.0918 (10)
H29	−0.0340	−0.1173	0.7276	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0432 (3)	0.0965 (5)	0.0761 (4)	0.0129 (3)	0.0307 (2)	−0.0009 (3)
Cl2	0.0595 (3)	0.0979 (5)	0.1025 (5)	−0.0085 (3)	0.0344 (3)	0.0410 (4)
O1	0.0376 (6)	0.0514 (8)	0.0557 (8)	0.0082 (6)	0.0145 (5)	−0.0118 (6)
O2	0.0620 (8)	0.0522 (8)	0.0423 (7)	0.0176 (6)	0.0172 (6)	−0.0053 (6)
C9	0.0268 (6)	0.0317 (7)	0.0319 (7)	0.0013 (6)	0.0077 (5)	−0.0011 (6)
C10	0.0334 (7)	0.0320 (8)	0.0362 (8)	0.0021 (6)	0.0108 (6)	−0.0002 (6)
C25	0.0366 (8)	0.0317 (8)	0.0331 (7)	0.0021 (6)	0.0102 (6)	−0.0006 (6)
C17	0.0280 (7)	0.0380 (8)	0.0377 (8)	−0.0003 (6)	0.0058 (6)	−0.0020 (6)
C1	0.0268 (7)	0.0431 (9)	0.0378 (8)	0.0014 (6)	0.0071 (6)	0.0029 (7)
C7	0.0273 (7)	0.0400 (9)	0.0399 (8)	0.0017 (6)	0.0082 (6)	0.0047 (7)
N1	0.0428 (8)	0.0347 (7)	0.0488 (8)	−0.0066 (6)	0.0065 (6)	0.0001 (6)
C6	0.0383 (9)	0.0485 (10)	0.0573 (11)	0.0094 (8)	0.0178 (8)	0.0096 (8)
C8	0.0276 (7)	0.0396 (8)	0.0344 (7)	0.0010 (6)	0.0083 (6)	0.0016 (6)
C18	0.0279 (7)	0.0455 (9)	0.0389 (8)	−0.0036 (6)	0.0013 (6)	0.0006 (7)
C26	0.0429 (9)	0.0324 (8)	0.0406 (9)	0.0075 (7)	0.0103 (7)	0.0020 (7)
C2	0.0313 (7)	0.0447 (9)	0.0410 (9)	0.0037 (7)	0.0082 (6)	0.0004 (7)
C3	0.0280 (7)	0.0638 (12)	0.0392 (9)	0.0030 (7)	0.0089 (6)	0.0001 (8)
C11	0.0386 (8)	0.0358 (8)	0.0352 (8)	−0.0032 (7)	0.0080 (6)	−0.0018 (6)
C16	0.0336 (8)	0.0457 (9)	0.0356 (8)	−0.0050 (7)	0.0055 (6)	0.0045 (7)
C35	0.0531 (10)	0.0342 (8)	0.0339 (8)	−0.0060 (7)	0.0132 (7)	0.0014 (6)
C36	0.0578 (11)	0.0364 (9)	0.0358 (8)	−0.0069 (8)	0.0029 (7)	0.0044 (7)
C24	0.0397 (9)	0.0416 (9)	0.0458 (9)	−0.0068 (7)	0.0020 (7)	−0.0038 (7)
C27	0.0452 (9)	0.0426 (10)	0.0452 (10)	0.0057 (8)	0.0012 (7)	0.0057 (8)
C4	0.0348 (8)	0.0651 (13)	0.0491 (10)	−0.0040 (8)	0.0103 (7)	0.0153 (9)
C23	0.0545 (11)	0.0560 (12)	0.0442 (10)	−0.0072 (9)	0.0084 (8)	−0.0038 (9)
C5	0.0462 (10)	0.0489 (11)	0.0652 (12)	0.0041 (8)	0.0146 (9)	0.0148 (9)
C15	0.0393 (9)	0.0862 (16)	0.0440 (10)	−0.0144 (10)	0.0026 (8)	0.0033 (10)
C19	0.0498 (10)	0.0540 (12)	0.0578 (12)	0.0095 (9)	0.0098 (9)	0.0082 (9)
C12	0.0575 (11)	0.0569 (12)	0.0439 (10)	−0.0085 (9)	0.0152 (9)	−0.0114 (9)
C31	0.0863 (16)	0.0539 (12)	0.0392 (10)	−0.0176 (11)	−0.0046 (10)	0.0067 (9)
C34	0.0725 (13)	0.0464 (11)	0.0488 (10)	−0.0088 (9)	0.0317 (10)	0.0003 (8)
C22	0.0663 (13)	0.0867 (18)	0.0395 (10)	−0.0265 (13)	0.0055 (9)	0.0027 (11)
C14	0.0606 (13)	0.109 (2)	0.0426 (11)	−0.0316 (14)	−0.0049 (10)	−0.0049 (12)
C37	0.0711 (14)	0.0378 (10)	0.0712 (14)	−0.0094 (9)	0.0088 (11)	0.0038 (10)
C13	0.0773 (16)	0.0891 (18)	0.0406 (11)	−0.0263 (14)	0.0072 (10)	−0.0181 (11)
C28	0.0535 (12)	0.0727 (16)	0.0739 (15)	0.0180 (11)	−0.0019 (11)	0.0078 (12)
C32	0.126 (2)	0.0698 (16)	0.0302 (10)	−0.0331 (16)	0.0127 (12)	0.0023 (10)
C21	0.0602 (13)	0.0862 (19)	0.0617 (14)	−0.0127 (13)	−0.0026 (11)	0.0319 (13)
C20	0.0660 (14)	0.0633 (15)	0.0866 (18)	0.0147 (12)	0.0085 (13)	0.0278 (13)
C33	0.116 (2)	0.0621 (14)	0.0454 (11)	−0.0251 (14)	0.0423 (14)	−0.0041 (10)
C30	0.093 (2)	0.087 (2)	0.0579 (15)	−0.0109 (16)	−0.0288 (15)	0.0166 (14)
C29	0.0645 (16)	0.103 (2)	0.092 (2)	0.0113 (16)	−0.0254 (15)	0.0192 (18)

Geometric parameters (Å, º) top

Cl1—C3	1.7219 (18)	C36—C27	1.401 (3)
Cl2—C4	1.7266 (19)	C36—C31	1.404 (3)
O1—C10	1.2141 (19)	C24—H24A	0.9700
O2—C26	1.210 (2)	C24—H24B	0.9700
C9—C10	1.529 (2)	C27—C28	1.373 (3)
C9—C8	1.541 (2)	C4—C5	1.382 (3)
C9—C17	1.560 (2)	C23—C22	1.387 (3)
C9—C25	1.603 (2)	C23—H23	0.9300
C10—C11	1.484 (2)	C5—H5	0.9300
C25—N1	1.459 (2)	C15—C14	1.376 (3)
C25—C35	1.515 (2)	C15—H15	0.9300
C25—C26	1.567 (2)	C19—C20	1.380 (3)
C17—C18	1.506 (2)	C19—H19	0.9300
C17—C24	1.516 (2)	C12—C13	1.368 (3)
C17—H17	0.9800	C12—H12	0.9300
C1—C6	1.383 (3)	C31—C30	1.409 (4)
C1—C2	1.385 (2)	C31—C32	1.412 (4)
C1—C7	1.518 (2)	C34—C33	1.413 (3)
C7—C16	1.512 (2)	C34—H34	0.9300
C7—C8	1.534 (2)	C22—C21	1.369 (4)
C7—H7	0.9800	C22—H22	0.9300
N1—C24	1.448 (2)	C14—C13	1.371 (4)
N1—C37	1.452 (2)	C14—H14	0.9300
C6—C5	1.375 (3)	C37—H37A	0.9600
C6—H6	0.9300	C37—H37B	0.9600
C8—H8A	0.9700	C37—H37C	0.9600
C8—H8B	0.9700	C13—H13	0.9300
C18—C23	1.383 (3)	C28—C29	1.410 (4)
C18—C19	1.385 (3)	C28—H28	0.9300
C26—C27	1.473 (3)	C32—C33	1.358 (4)
C2—C3	1.388 (2)	C32—H32	0.9300
C2—H2	0.9300	C21—C20	1.365 (4)
C3—C4	1.380 (3)	C21—H21	0.9300
C11—C16	1.391 (2)	C20—H20	0.9300
C11—C12	1.401 (2)	C33—H33	0.9300
C16—C15	1.396 (2)	C30—C29	1.356 (5)
C35—C34	1.367 (3)	C30—H30	0.9300
C35—C36	1.397 (3)	C29—H29	0.9300

C10—C9—C8	105.82 (12)	C17—C24—H24A	111.5
C10—C9—C17	111.28 (12)	N1—C24—H24B	111.5
C8—C9—C17	111.75 (12)	C17—C24—H24B	111.5
C10—C9—C25	109.40 (12)	H24A—C24—H24B	109.3
C8—C9—C25	116.04 (12)	C28—C27—C36	120.44 (19)
C17—C9—C25	102.65 (12)	C28—C27—C26	132.5 (2)
O1—C10—C11	120.92 (15)	C36—C27—C26	107.09 (16)
O1—C10—C9	122.52 (14)	C3—C4—C5	119.47 (17)
C11—C10—C9	116.55 (13)	C3—C4—Cl2	121.45 (15)
N1—C25—C35	111.22 (13)	C5—C4—Cl2	119.07 (17)
N1—C25—C26	113.12 (13)	C18—C23—C22	120.8 (2)
C35—C25—C26	101.58 (13)	C18—C23—H23	119.6
N1—C25—C9	103.72 (12)	C22—C23—H23	119.6
C35—C25—C9	115.68 (13)	C6—C5—C4	120.22 (19)
C26—C25—C9	111.90 (12)	C6—C5—H5	119.9
C18—C17—C24	116.94 (14)	C4—C5—H5	119.9
C18—C17—C9	116.44 (13)	C14—C15—C16	120.8 (2)
C24—C17—C9	103.44 (13)	C14—C15—H15	119.6
C18—C17—H17	106.4	C16—C15—H15	119.6
C24—C17—H17	106.4	C20—C19—C18	121.2 (2)
C9—C17—H17	106.4	C20—C19—H19	119.4
C6—C1—C2	118.46 (16)	C18—C19—H19	119.4
C6—C1—C7	121.07 (14)	C13—C12—C11	120.4 (2)
C2—C1—C7	120.46 (16)	C13—C12—H12	119.8
C16—C7—C1	111.05 (14)	C11—C12—H12	119.8
C16—C7—C8	112.58 (13)	C36—C31—C30	115.2 (2)
C1—C7—C8	110.86 (13)	C36—C31—C32	115.5 (2)
C16—C7—H7	107.4	C30—C31—C32	129.3 (2)
C1—C7—H7	107.4	C35—C34—C33	117.9 (2)
C8—C7—H7	107.4	C35—C34—H34	121.0
C24—N1—C37	116.63 (16)	C33—C34—H34	121.0
C24—N1—C25	108.04 (13)	C21—C22—C23	120.5 (2)
C37—N1—C25	116.51 (16)	C21—C22—H22	119.7
C5—C6—C1	121.11 (17)	C23—C22—H22	119.7
C5—C6—H6	119.4	C13—C14—C15	120.3 (2)
C1—C6—H6	119.4	C13—C14—H14	119.9
C7—C8—C9	115.71 (13)	C15—C14—H14	119.9
C7—C8—H8A	108.4	N1—C37—H37A	109.5
C9—C8—H8A	108.4	N1—C37—H37B	109.5
C7—C8—H8B	108.4	H37A—C37—H37B	109.5
C9—C8—H8B	108.4	N1—C37—H37C	109.5
H8A—C8—H8B	107.4	H37A—C37—H37C	109.5
C23—C18—C19	117.65 (18)	H37B—C37—H37C	109.5
C23—C18—C17	123.25 (17)	C12—C13—C14	120.2 (2)
C19—C18—C17	119.10 (16)	C12—C13—H13	119.9
O2—C26—C27	127.58 (16)	C14—C13—H13	119.9
O2—C26—C25	124.35 (16)	C27—C28—C29	117.0 (3)
C27—C26—C25	107.98 (14)	C27—C28—H28	121.5
C1—C2—C3	120.70 (17)	C29—C28—H28	121.5
C1—C2—H2	119.6	C33—C32—C31	120.6 (2)
C3—C2—H2	119.6	C33—C32—H32	119.7
C4—C3—C2	120.02 (16)	C31—C32—H32	119.7
C4—C3—Cl1	120.86 (14)	C20—C21—C22	119.3 (2)
C2—C3—Cl1	119.11 (15)	C20—C21—H21	120.4
C16—C11—C12	119.67 (16)	C22—C21—H21	120.4
C16—C11—C10	121.56 (15)	C21—C20—C19	120.5 (3)
C12—C11—C10	118.67 (16)	C21—C20—H20	119.7
C11—C16—C15	118.65 (17)	C19—C20—H20	119.7
C11—C16—C7	121.94 (14)	C32—C33—C34	122.9 (2)
C15—C16—C7	119.40 (16)	C32—C33—H33	118.5
C34—C35—C36	119.14 (18)	C34—C33—H33	118.5
C34—C35—C25	131.44 (18)	C29—C30—C31	121.7 (2)
C36—C35—C25	109.43 (15)	C29—C30—H30	119.1
C35—C36—C27	113.24 (16)	C31—C30—H30	119.1
C35—C36—C31	123.9 (2)	C30—C29—C28	122.7 (3)
C27—C36—C31	122.9 (2)	C30—C29—H29	118.6
N1—C24—C17	101.37 (14)	C28—C29—H29	118.6
N1—C24—H24A	111.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2	0.97	2.49	3.045 (2)	116
C17—H17···O1	0.98	2.33	2.794 (2)	108
C32—H32···O2ⁱ	0.93	2.48	3.351 (3)	156

Symmetry code: (i) x, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₇H₂₇Cl₂NO₂
M_r	588.50
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	39.6142 (12), 8.3031 (2), 18.1810 (5)
β (°)	101.135 (3)
V (Å³)	5867.5 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.976, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	67467, 8160, 5776
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.695

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.152, 1.06
No. of reflections	8160
No. of parameters	380
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.32

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2	0.97	2.49	3.045 (2)	116.0
C17—H17···O1	0.98	2.33	2.794 (2)	108.2
C32—H32···O2ⁱ	0.9300	2.4800	3.351 (3)	156.00

Symmetry code: (i) x, −y, z+1/2.

References

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ramesh, P., Murugavel, S., Pandi, A. S., Murugan, R. & Narayanan, S. S. (2007). Acta Cryst. E63, o4851. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sarala, G., Kavitha, C. V., Mantelingu, K., Anandalwar, S. M., Shashidhara Prasad, J. & Rangappa, K. S. (2006). Anal. Sci. 22, x241–x242. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Welch, W. M., Kraska, A. R., Sarges, R. & Koe, K. B. (1984). J. Med. Chem. 27, 1508–1510. CrossRef CAS PubMed Web of Science Google Scholar

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Volume 64| Part 6| June 2008| Page o1089

doi:10.1107/S1600536808013846

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

(4S)-4-(3,4-Di­chloro­phen­yl)-1′-methyl-4′-phenyl-3,4-di­hydro­naphthalene-2-spiro-3′-pyrrolidine-2′-spiro-1′′-ace­naphthyl­ene-1,2′′(2H,1′′H)-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(4S)-4-(3,4-Dichlorophenyl)-1′-methyl-4′-phenyl-3,4-dihydronaphthalene-2-spiro-3′-pyrrolidine-2′-spiro-1′′-acenaphthylene-1,2′′(2H,1′′H)-dione