3′-Benzoyl-1′-methyl-4′-phenyl­spiro[acenaphthyl­ene-1(2H),2′-pyrrolidin]-2-one

Augustine, T.; Vithiya, S.M.; Ignacimuthu, S.; Ramkumar, V.

doi:10.1107/S160053681004376X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o3002

https://doi.org/10.1107/S160053681004376X

Open

access

3′-Benzoyl-1′-methyl-4′-phenylspiro[acenaphthylene-1(2H),2′-pyrrolidin]-2-one

T. Augustine,^a ^* Scholastica Mary Vithiya,^b S. Ignacimuthu ^c and V. Ramkumar ^d

^aDepartment of Chemistry, D. G. Vaishnav College, Chennai 106, Tamil Nadu, India, ^bDepartment of Chemistry, Auxilium College, Vellore, Tamil Nadu, India, ^cEntomology Research Institute, Loyola College, Chennai 34, Tamil Nadu, India, and ^dDepartment of Chemistry, Indian Institute of Technology Madras, Chennai 36, Tamil Nadu, India
^*Correspondence e-mail: augustineap@gmail.com

(Received 25 October 2010; accepted 26 October 2010; online 31 October 2010)

In the title compound, C₂₉H₂₃NO₂, the pyrrolidine ring adopts a twisted conformation about one of the C—N bonds. The acenaphthone ring (r.m.s. deviation = 0.025 Å) lies almost perpendicular to the pyrrolidine ring [dihedral angle = 88.08 (8)°]. The dihedral angle between the phenyl rings is 88.12 (11)°. In the crystal structure, weak C—H⋯π interactions connect the molecules.

Related literature

For background on 1,3-dipolar cycloadditions, see: Grigg (1987 ); Huisgen (1988 ); Bridges et al. (1993 ); Padwa (1984 ). For a related structure, see: Augustine et al. (2007 ). For ring conformation analysis, see: Cremer & Pople (1975 ); Rao et al. (1981 ).

Experimental

Crystal data

C₂₉H₂₃NO₂
M_r = 417.48
Monoclinic, P 2₁ /c
a = 8.6462 (4) Å
b = 15.8352 (8) Å
c = 16.7174 (8) Å
β = 99.827 (2)°
V = 2255.27 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.42 × 0.34 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.969, T_max = 0.983
16782 measured reflections
5549 independent reflections
2944 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.142
S = 1.02
5549 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg5ⁱ	0.93	2.85	3.638 (2)	144
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681004376X/hb5706sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004376X/hb5706Isup2.hkl

checkCIF report

Comment top

1,3-dipolar cycloadditions using azomethine ylides is conceptually the most simple and efficient method for the construction of saturated, nitrogen containing five-membered heterocycles (Padwa, 1984). Ylide generation, often performed in situ (Grigg, 1987), followed by cycloaddition with suitable dipolarophiles furnishes pyrrolidines and pyrroles in only one step from simple starting materials (Huisgen, 1988). 1,3-dipolar cycloadditions of azomethine ylides with olefinic and acetylenic dipolarophiles represent an important approach for the formation of pyrrolidines and pyrrolizines which are prevalent in a variety of biologically active compounds (Bridges et al., 1993). In view of this we have determined the structure of the title compound.

In the title compound C₂₉H₂₃NO₂, the C—O bond distance (1.21 Å) of the carbonyl group in the benzoyl moiety indicates n-p overlap. The bond angles and dihedral angle of C9—C12—C1 (101.69 Å) of the acenapthone ring indicate it to be in a plane nearly perpendicular to the pyrrolidine ring. The sum of the angles around N-atom of the pyrrolidine ring accounts for 338.78°. This indicates that the structure approaches pyramidal shape. The study of torsion angle, asymmetry parameters and least-square plane calculation shows that the pyrrolidine ring adopts a envelope conformation and puckered, Q₂ = 0.4030 (18) Å, φ = 333.0 (3)° (Cremer & Pople, 1975). The Pseudorotation parameter P and τ are 136.4 (1)° and 43.71 (1)° respectively (Rao et al., 1981) showing that C15 and N1 are twisted and puckered.

The crystal structure is stabilized by weak C—H···π interactions.

Related literature top

For background on 1,3-dipolar cycloadditions, see: Grigg (1987); Huisgen (1988); Bridges et al. (1993); Padwa (1984). For a related structure, see: Augustine et al. (2007). For ring conformation analysis, see: Cremer & Pople (1975); Rao et al. (1981).

Experimental top

A mixture of chalcone [1,3-diphenyl-2-propen-1-one] (0.40 g, 2 mmol), acenaphthenequinone (0.36 g, 2 mmol), sarcosine (0.17 g, 2 mmol) and methanol (25 ml) was heated for four hours using oil bath using a dimmerstat at a temperature of 40° C. The reaction mixture was cooled to room temperature and poured into ice-cold water. The solid mass obtained was filtered, washed with water, dried and colourless blocks of (I) were obtained by recrystallization using acetone as solvent by slow evaporation method.

Structure description top

The crystal structure is stabilized by weak C—H···π interactions.

For background on 1,3-dipolar cycloadditions, see: Grigg (1987); Huisgen (1988); Bridges et al. (1993); Padwa (1984). For a related structure, see: Augustine et al. (2007). For ring conformation analysis, see: Cremer & Pople (1975); Rao et al. (1981).

Computing details top

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

Figures top

	Fig. 1. View of (I) with atoms represented as 30% probability ellipsoids.
	Fig. 2. Packing diagram showing the C—H···π interactions.

3'-Benzoyl-1'-methyl-4'-phenylspiro[acenaphthylene-1(2H),2'- pyrrolidin]-2-one top

Crystal data top

C₂₉H₂₃NO₂	F(000) = 880
M_r = 417.48	D_x = 1.230 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3350 reflections
a = 8.6462 (4) Å	θ = 2.5–25.3°
b = 15.8352 (8) Å	µ = 0.08 mm⁻¹
c = 16.7174 (8) Å	T = 298 K
β = 99.827 (2)°	Block, colourless
V = 2255.27 (19) Å³	0.42 × 0.34 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	5549 independent reflections
Radiation source: fine-focus sealed tube	2944 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
φ and ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→11
T_min = 0.969, T_max = 0.983	k = −18→20
16782 measured reflections	l = −22→22

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0566P)² + 0.296P] where P = (F_o² + 2F_c²)/3
5549 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₉H₂₃NO₂	V = 2255.27 (19) Å³
M_r = 417.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6462 (4) Å	µ = 0.08 mm⁻¹
b = 15.8352 (8) Å	T = 298 K
c = 16.7174 (8) Å	0.42 × 0.34 × 0.22 mm
β = 99.827 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5549 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2944 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.983	R_int = 0.035
16782 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
5549 reflections	Δρ_min = −0.19 e Å⁻³
290 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
C1	0.2530 (2)	0.32056 (11)	0.28710 (10)	0.0505 (5)
C2	0.3044 (2)	0.27558 (11)	0.21910 (10)	0.0523 (5)
C3	0.4124 (3)	0.21283 (14)	0.21511 (14)	0.0848 (7)
H3	0.4681	0.1887	0.2621	0.102*
C4	0.4365 (4)	0.18600 (16)	0.13784 (16)	0.1013 (9)
H4	0.5112	0.1445	0.1344	0.122*
C5	0.3546 (3)	0.21865 (15)	0.06826 (14)	0.0845 (7)
H5	0.3733	0.1985	0.0185	0.101*
C6	0.1491 (3)	0.32230 (14)	0.00346 (11)	0.0643 (6)
H6	0.1588	0.3072	−0.0492	0.077*
C7	0.0454 (2)	0.38280 (14)	0.01609 (11)	0.0631 (6)
H7	−0.0157	0.4080	−0.0288	0.076*
C8	0.0257 (2)	0.40942 (12)	0.09475 (11)	0.0549 (5)
H8	−0.0478	0.4506	0.1012	0.066*
C9	0.11632 (19)	0.37362 (10)	0.16061 (9)	0.0413 (4)
C10	0.2211 (2)	0.31009 (10)	0.14725 (9)	0.0430 (4)
C11	0.2423 (2)	0.28227 (12)	0.06998 (10)	0.0555 (5)
C12	0.13015 (19)	0.38914 (10)	0.25123 (9)	0.0414 (4)
C13	0.19337 (19)	0.47786 (10)	0.28373 (9)	0.0402 (4)
H13	0.2961	0.4699	0.3181	0.048*
C14	0.0763 (2)	0.50907 (11)	0.33801 (10)	0.0497 (5)
H14	−0.0009	0.5458	0.3051	0.060*
C15	−0.0067 (2)	0.42866 (13)	0.35599 (12)	0.0637 (6)
H15A	0.0552	0.3972	0.4000	0.076*
H15B	−0.1090	0.4407	0.3697	0.076*
C16	0.2127 (2)	0.53926 (11)	0.21632 (10)	0.0447 (4)
C17	0.35855 (19)	0.53647 (11)	0.17984 (9)	0.0437 (4)
C18	0.4852 (2)	0.48560 (13)	0.20867 (12)	0.0612 (5)
H18	0.4812	0.4498	0.2524	0.073*
C19	0.6179 (3)	0.48749 (17)	0.17315 (16)	0.0906 (8)
H19	0.7031	0.4531	0.1929	0.109*
C20	0.6240 (3)	0.53984 (19)	0.10893 (17)	0.1026 (9)
H20	0.7140	0.5412	0.0854	0.123*
C21	0.5004 (3)	0.58984 (18)	0.07900 (14)	0.0889 (8)
H21	0.5055	0.6248	0.0348	0.107*
C22	0.3676 (2)	0.58877 (13)	0.11399 (11)	0.0625 (5)
H22	0.2831	0.6233	0.0934	0.075*
C23	0.1560 (2)	0.55919 (11)	0.41019 (11)	0.0495 (5)
C24	0.1259 (3)	0.64403 (13)	0.41745 (13)	0.0690 (6)
H24	0.0502	0.6700	0.3791	0.083*
C25	0.2064 (3)	0.69126 (16)	0.48084 (18)	0.0879 (8)
H25	0.1839	0.7484	0.4845	0.105*
C26	0.3172 (3)	0.65544 (18)	0.53761 (16)	0.0827 (7)
H26	0.3726	0.6878	0.5794	0.099*
C27	0.3463 (3)	0.57130 (17)	0.53253 (13)	0.0767 (7)
H27	0.4204	0.5456	0.5719	0.092*
C28	0.2670 (2)	0.52382 (14)	0.46946 (12)	0.0649 (6)
H28	0.2890	0.4665	0.4669	0.078*
C29	−0.0869 (3)	0.29814 (14)	0.28011 (14)	0.0825 (7)
H29A	−0.0220	0.2644	0.3202	0.124*
H29B	−0.0912	0.2728	0.2276	0.124*
H29C	−0.1908	0.3015	0.2928	0.124*
N1	−0.02068 (18)	0.38299 (10)	0.27962 (9)	0.0565 (4)
O2	0.29920 (19)	0.30958 (9)	0.35906 (7)	0.0752 (4)
O3	0.10953 (17)	0.58979 (9)	0.19095 (8)	0.0704 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0700 (12)	0.0418 (10)	0.0407 (10)	0.0002 (9)	0.0121 (8)	0.0050 (8)
C2	0.0703 (12)	0.0418 (10)	0.0463 (10)	0.0078 (10)	0.0138 (9)	0.0029 (8)
C3	0.1170 (19)	0.0658 (15)	0.0715 (14)	0.0422 (14)	0.0160 (13)	0.0069 (12)
C4	0.135 (2)	0.0850 (18)	0.0903 (19)	0.0531 (17)	0.0388 (17)	−0.0077 (15)
C5	0.1157 (19)	0.0786 (16)	0.0668 (15)	0.0179 (15)	0.0375 (14)	−0.0189 (13)
C6	0.0806 (15)	0.0741 (15)	0.0382 (10)	−0.0217 (12)	0.0106 (10)	−0.0067 (10)
C7	0.0625 (13)	0.0805 (15)	0.0414 (10)	−0.0169 (12)	−0.0050 (9)	0.0092 (10)
C8	0.0464 (10)	0.0618 (12)	0.0555 (11)	−0.0014 (9)	0.0062 (8)	0.0051 (9)
C9	0.0441 (9)	0.0410 (10)	0.0398 (9)	−0.0050 (8)	0.0098 (7)	0.0027 (7)
C10	0.0528 (10)	0.0395 (10)	0.0386 (9)	−0.0040 (8)	0.0129 (7)	−0.0022 (7)
C11	0.0707 (12)	0.0539 (12)	0.0455 (10)	−0.0071 (10)	0.0198 (9)	−0.0088 (9)
C12	0.0501 (10)	0.0378 (9)	0.0396 (8)	0.0014 (8)	0.0175 (7)	0.0017 (7)
C13	0.0441 (9)	0.0386 (9)	0.0415 (8)	0.0031 (7)	0.0172 (7)	0.0002 (7)
C14	0.0521 (10)	0.0487 (11)	0.0541 (10)	0.0063 (9)	0.0252 (8)	−0.0007 (8)
C15	0.0715 (13)	0.0652 (13)	0.0648 (12)	−0.0122 (11)	0.0412 (10)	−0.0122 (10)
C16	0.0509 (10)	0.0371 (10)	0.0484 (10)	0.0014 (9)	0.0153 (8)	−0.0006 (8)
C17	0.0460 (10)	0.0441 (10)	0.0435 (9)	−0.0115 (8)	0.0149 (7)	−0.0033 (8)
C18	0.0554 (12)	0.0624 (13)	0.0707 (12)	0.0027 (10)	0.0244 (10)	0.0129 (10)
C19	0.0621 (14)	0.1001 (19)	0.119 (2)	0.0144 (13)	0.0434 (14)	0.0281 (16)
C20	0.0779 (17)	0.128 (2)	0.118 (2)	0.0117 (18)	0.0625 (16)	0.0354 (19)
C21	0.0830 (17)	0.117 (2)	0.0747 (15)	−0.0113 (16)	0.0368 (13)	0.0311 (15)
C22	0.0587 (12)	0.0762 (14)	0.0537 (11)	−0.0109 (11)	0.0126 (9)	0.0105 (10)
C23	0.0562 (11)	0.0480 (11)	0.0510 (10)	0.0038 (9)	0.0284 (9)	−0.0048 (8)
C24	0.0813 (15)	0.0529 (13)	0.0771 (14)	0.0102 (11)	0.0261 (11)	−0.0052 (11)
C25	0.106 (2)	0.0577 (15)	0.109 (2)	−0.0035 (14)	0.0435 (17)	−0.0292 (15)
C26	0.0799 (17)	0.096 (2)	0.0821 (16)	−0.0169 (15)	0.0407 (14)	−0.0399 (15)
C27	0.0698 (14)	0.106 (2)	0.0576 (13)	0.0073 (13)	0.0194 (11)	−0.0129 (13)
C28	0.0769 (14)	0.0605 (13)	0.0610 (12)	0.0120 (11)	0.0228 (11)	−0.0084 (10)
C29	0.0991 (17)	0.0744 (16)	0.0854 (16)	−0.0376 (14)	0.0483 (13)	−0.0165 (12)
N1	0.0604 (10)	0.0557 (10)	0.0611 (10)	−0.0151 (8)	0.0322 (8)	−0.0083 (7)
O2	0.1194 (12)	0.0654 (9)	0.0392 (7)	0.0163 (8)	0.0087 (7)	0.0095 (6)
O3	0.0751 (9)	0.0600 (9)	0.0827 (10)	0.0249 (8)	0.0324 (7)	0.0237 (8)

Geometric parameters (Å, º) top

C1—O2	1.2136 (19)	C15—H15A	0.9700
C1—C2	1.473 (2)	C15—H15B	0.9700
C1—C12	1.565 (2)	C16—O3	1.219 (2)
C2—C3	1.373 (3)	C16—C17	1.492 (2)
C2—C10	1.402 (2)	C17—C18	1.379 (3)
C3—C4	1.409 (3)	C17—C22	1.390 (2)
C3—H3	0.9300	C18—C19	1.379 (3)
C4—C5	1.357 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.364 (3)
C5—C11	1.403 (3)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.355 (3)
C6—C7	1.353 (3)	C20—H20	0.9300
C6—C11	1.408 (3)	C21—C22	1.375 (3)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.418 (3)	C22—H22	0.9300
C7—H7	0.9300	C23—C28	1.375 (3)
C8—C9	1.361 (2)	C23—C24	1.378 (3)
C8—H8	0.9300	C24—C25	1.384 (3)
C9—C10	1.397 (2)	C24—H24	0.9300
C9—C12	1.519 (2)	C25—C26	1.353 (3)
C10—C11	1.406 (2)	C25—H25	0.9300
C12—N1	1.465 (2)	C26—C27	1.361 (3)
C12—C13	1.571 (2)	C26—H26	0.9300
C13—C16	1.519 (2)	C27—C28	1.379 (3)
C13—C14	1.551 (2)	C27—H27	0.9300
C13—H13	0.9800	C28—H28	0.9300
C14—C23	1.509 (2)	C29—N1	1.461 (2)
C14—C15	1.516 (3)	C29—H29A	0.9600
C14—H14	0.9800	C29—H29B	0.9600
C15—N1	1.454 (2)	C29—H29C	0.9600

O2—C1—C2	127.16 (17)	C14—C15—H15A	111.3
O2—C1—C12	124.49 (16)	N1—C15—H15B	111.3
C2—C1—C12	108.31 (14)	C14—C15—H15B	111.3
C3—C2—C10	119.66 (17)	H15A—C15—H15B	109.2
C3—C2—C1	133.22 (18)	O3—C16—C17	119.76 (15)
C10—C2—C1	107.11 (15)	O3—C16—C13	120.78 (15)
C2—C3—C4	118.1 (2)	C17—C16—C13	119.45 (15)
C2—C3—H3	120.9	C18—C17—C22	118.44 (17)
C4—C3—H3	120.9	C18—C17—C16	123.43 (15)
C5—C4—C3	122.3 (2)	C22—C17—C16	118.12 (16)
C5—C4—H4	118.9	C17—C18—C19	120.42 (19)
C3—C4—H4	118.9	C17—C18—H18	119.8
C4—C5—C11	121.20 (19)	C19—C18—H18	119.8
C4—C5—H5	119.4	C20—C19—C18	119.9 (2)
C11—C5—H5	119.4	C20—C19—H19	120.0
C7—C6—C11	120.06 (17)	C18—C19—H19	120.0
C7—C6—H6	120.0	C21—C20—C19	120.8 (2)
C11—C6—H6	120.0	C21—C20—H20	119.6
C6—C7—C8	122.84 (18)	C19—C20—H20	119.6
C6—C7—H7	118.6	C20—C21—C22	119.9 (2)
C8—C7—H7	118.6	C20—C21—H21	120.0
C9—C8—C7	118.87 (18)	C22—C21—H21	120.0
C9—C8—H8	120.6	C21—C22—C17	120.5 (2)
C7—C8—H8	120.6	C21—C22—H22	119.7
C8—C9—C10	118.02 (15)	C17—C22—H22	119.7
C8—C9—C12	132.51 (16)	C28—C23—C24	116.91 (19)
C10—C9—C12	109.46 (13)	C28—C23—C14	121.96 (17)
C9—C10—C2	113.33 (14)	C24—C23—C14	121.06 (18)
C9—C10—C11	124.21 (16)	C23—C24—C25	121.1 (2)
C2—C10—C11	122.45 (16)	C23—C24—H24	119.4
C5—C11—C10	116.29 (18)	C25—C24—H24	119.4
C5—C11—C6	127.74 (18)	C26—C25—C24	120.9 (2)
C10—C11—C6	115.96 (18)	C26—C25—H25	119.5
N1—C12—C9	112.92 (13)	C24—C25—H25	119.5
N1—C12—C1	114.40 (13)	C25—C26—C27	118.9 (2)
C9—C12—C1	101.69 (12)	C25—C26—H26	120.6
N1—C12—C13	102.93 (12)	C27—C26—H26	120.6
C9—C12—C13	116.96 (13)	C26—C27—C28	120.5 (2)
C1—C12—C13	108.34 (13)	C26—C27—H27	119.7
C16—C13—C14	113.29 (13)	C28—C27—H27	119.7
C16—C13—C12	113.06 (13)	C23—C28—C27	121.6 (2)
C14—C13—C12	105.31 (13)	C23—C28—H28	119.2
C16—C13—H13	108.3	C27—C28—H28	119.2
C14—C13—H13	108.3	N1—C29—H29A	109.5
C12—C13—H13	108.3	N1—C29—H29B	109.5
C23—C14—C15	116.74 (15)	H29A—C29—H29B	109.5
C23—C14—C13	112.37 (14)	N1—C29—H29C	109.5
C15—C14—C13	103.08 (14)	H29A—C29—H29C	109.5
C23—C14—H14	108.1	H29B—C29—H29C	109.5
C15—C14—H14	108.1	C15—N1—C29	115.24 (15)
C13—C14—H14	108.1	C15—N1—C12	107.82 (14)
N1—C15—C14	102.41 (14)	C29—N1—C12	115.72 (15)
N1—C15—H15A	111.3

O2—C1—C2—C3	−0.6 (4)	C9—C12—C13—C14	131.26 (14)
C12—C1—C2—C3	177.3 (2)	C1—C12—C13—C14	−114.66 (14)
O2—C1—C2—C10	−179.13 (18)	C16—C13—C14—C23	−90.89 (18)
C12—C1—C2—C10	−1.20 (19)	C12—C13—C14—C23	145.06 (14)
C10—C2—C3—C4	0.7 (3)	C16—C13—C14—C15	142.59 (16)
C1—C2—C3—C4	−177.7 (2)	C12—C13—C14—C15	18.54 (17)
C2—C3—C4—C5	−1.5 (4)	C23—C14—C15—N1	−161.09 (15)
C3—C4—C5—C11	0.9 (4)	C13—C14—C15—N1	−37.41 (19)
C11—C6—C7—C8	0.6 (3)	C14—C13—C16—O3	−24.2 (2)
C6—C7—C8—C9	0.9 (3)	C12—C13—C16—O3	95.49 (18)
C7—C8—C9—C10	−2.1 (2)	C14—C13—C16—C17	156.88 (14)
C7—C8—C9—C12	177.34 (17)	C12—C13—C16—C17	−83.41 (18)
C8—C9—C10—C2	−177.88 (16)	O3—C16—C17—C18	175.23 (18)
C12—C9—C10—C2	2.6 (2)	C13—C16—C17—C18	−5.9 (2)
C8—C9—C10—C11	1.9 (3)	O3—C16—C17—C22	−3.9 (2)
C12—C9—C10—C11	−177.67 (16)	C13—C16—C17—C22	174.97 (16)
C3—C2—C10—C9	−179.55 (18)	C22—C17—C18—C19	0.6 (3)
C1—C2—C10—C9	−0.8 (2)	C16—C17—C18—C19	−178.6 (2)
C3—C2—C10—C11	0.7 (3)	C17—C18—C19—C20	−0.1 (4)
C1—C2—C10—C11	179.43 (16)	C18—C19—C20—C21	−0.5 (4)
C4—C5—C11—C10	0.5 (3)	C19—C20—C21—C22	0.7 (4)
C4—C5—C11—C6	179.7 (2)	C20—C21—C22—C17	−0.2 (4)
C9—C10—C11—C5	179.02 (18)	C18—C17—C22—C21	−0.4 (3)
C2—C10—C11—C5	−1.3 (3)	C16—C17—C22—C21	178.81 (19)
C9—C10—C11—C6	−0.4 (3)	C15—C14—C23—C28	55.7 (2)
C2—C10—C11—C6	179.36 (17)	C13—C14—C23—C28	−63.1 (2)
C7—C6—C11—C5	179.8 (2)	C15—C14—C23—C24	−127.57 (19)
C7—C6—C11—C10	−0.9 (3)	C13—C14—C23—C24	113.66 (18)
C8—C9—C12—N1	54.5 (2)	C28—C23—C24—C25	1.2 (3)
C10—C9—C12—N1	−126.08 (15)	C14—C23—C24—C25	−175.76 (18)
C8—C9—C12—C1	177.53 (18)	C23—C24—C25—C26	0.0 (3)
C10—C9—C12—C1	−3.02 (17)	C24—C25—C26—C27	−1.4 (4)
C8—C9—C12—C13	−64.7 (2)	C25—C26—C27—C28	1.6 (3)
C10—C9—C12—C13	114.74 (16)	C24—C23—C28—C27	−1.0 (3)
O2—C1—C12—N1	−57.4 (2)	C14—C23—C28—C27	175.89 (17)
C2—C1—C12—N1	124.57 (15)	C26—C27—C28—C23	−0.4 (3)
O2—C1—C12—C9	−179.48 (18)	C14—C15—N1—C29	175.49 (17)
C2—C1—C12—C9	2.53 (17)	C14—C15—N1—C12	44.53 (19)
O2—C1—C12—C13	56.7 (2)	C9—C12—N1—C15	−158.77 (15)
C2—C1—C12—C13	−121.27 (15)	C1—C12—N1—C15	85.56 (17)
N1—C12—C13—C16	−117.34 (15)	C13—C12—N1—C15	−31.75 (17)
C9—C12—C13—C16	7.1 (2)	C9—C12—N1—C29	70.5 (2)
C1—C12—C13—C16	121.15 (15)	C1—C12—N1—C29	−45.1 (2)
N1—C12—C13—C14	6.86 (16)	C13—C12—N1—C29	−162.45 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg5ⁱ	0.93	2.85	3.638 (2)	144

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

Experimental details

Crystal data
Chemical formula	C₂₉H₂₃NO₂
M_r	417.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.6462 (4), 15.8352 (8), 16.7174 (8)
β (°)	99.827 (2)
V (Å³)	2255.27 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.42 × 0.34 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.969, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	16782, 5549, 2944
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.142, 1.02
No. of reflections	5549
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg5ⁱ	0.93	2.85	3.638 (2)	144

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

Acknowledgements

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

References

Augustine, T., Ramkumar, V., Arul Antony, S. & Kanakam, C. C. (2007). Acta Cryst. E63, o4412. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bridges, R. J., Lovering, F. E., Humphrey, J. M., Stanley, M. S., Blakely, T. N., Cristofaro, M. F. & Chamberlin, A. R. (1993). Bioorg. Med. Chem. Lett. 3, 115–121. CrossRef CAS Web of Science Google Scholar
Bruker (2004). SADABS, APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Grigg, G. (1987). Chem. Soc. Rev. 16, 89–121. CrossRef CAS Web of Science Google Scholar
Huisgen, R. (1988). Adv. Cycloaddition, 1, 1–31. CAS Google Scholar
Padwa, A. (1984). 1,3-Dipolar Addition Chemistry. New York: John Wiley. Google Scholar
Rao, S. T., Westhof, E. & Sundaralingam, M. (1981). Acta Cryst. A37, 421–425. CrossRef CAS IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS 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 66| Part 11| November 2010| Page o3002

https://doi.org/10.1107/S160053681004376X

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

3′-Benzoyl-1′-methyl-4′-phenyl­spiro[ace­naphthyl­ene-1(2H),2′-pyrrolidin]-2-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3′-Benzoyl-1′-methyl-4′-phenylspiro[acenaphthylene-1(2H),2′-pyrrolidin]-2-one