14a-Hy­droxy-12-methyl-10-(4-methyl­phen­yl)-8,9,9a,10,12,13,14,14a-octa­hydro-10a,14-methano-5H-indeno­[2′,1′:4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione

Nagalakshmi, R.A.; Suresh, J.; Malathi, K.; Kumar, R.R.; Lakshman, P.L.N.

doi:10.1107/S1600536813025592

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1581

doi:10.1107/S1600536813025592

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14a-Hydroxy-12-methyl-10-(4-methylphenyl)-8,9,9a,10,12,13,14,14a-octahydro-10a,14-methano-5H-indeno[2′,1′:4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione

R. A. Nagalakshmi,^a J. Suresh,^a K. Malathi,^b R. Ranjith Kumar ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: plakshmannilantha@ymail.com

(Received 7 September 2013; accepted 15 September 2013; online 21 September 2013)

In the title compound, C₂₇H₂₈N₂O₃, each of the pyrrolidine rings adopts a twisted conformation, as does the cyclopentane ring. The indane ring has an r.m.s deviation of 0.0693 Å. The dihedral angle between the mean plane of the pyrrolizine ring and indane system is 82.58 (1)°. The piperidine ring has the methyl substituent in an equatorial position and adopts a twisted chair conformation. The molecular structure is stabilized by a weak intramolecular O—H⋯N interaction.

CCDC reference: 960966

Related literature

For the importance of pyrrazole derivatives, see: Mahajan et al. (1991 ); Katayama & Oshiyama (1997 ); Baraldi et al. (1998 ). For additional conformation analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₇H₂₈N₂O₃
M_r = 428.51
Monoclinic, P 2₁ /c
a = 16.8684 (6) Å
b = 8.3754 (3) Å
c = 15.9930 (6) Å
β = 96.658 (1)°
V = 2244.25 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.967, T_max = 0.974
28459 measured reflections
6850 independent reflections
4500 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.161
S = 1.02
6850 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.82	2.13	2.6497 (16)	121
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 960966

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813025592/tk5254sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813025592/tk5254Isup2.hkl

checkCIF report

Comment top

Pyrazole derivatives in general are well known nitrogen-containing heterocyclic compounds that have been the subject of enormous research due to their importance in various applications and their widespread potential biological and pharmacological activities such as anti-microbial (Mahajan et al., 1991), anti-viral (Baraldi et al., 1998), anti-tumor (Katayama & Oshiyama, 1997) and anti-fungal (Baraldi et al., 1998). In view of its medicinal importance we report the crystal structure of the title compound.

In the title compound (Fig. 1), each of the pyrrolidine rings A and B adopts twisted conformation with the puckering parameters (Cremer & Pople, 1975): q₂ = 0.4201 (14) Å, Φ₂ = 10.43 (19)° and q₂ = 0.4547 (16) Å, Φ₂ = 196.1 (2)° respectively. The sum of bond angles around N1 (335.69 (2)°) and N2 (340.55 (2)°) indicates sp³ hybridization. The N2—C11 = 1.462 (12) Å and N2—C8 = 1.463 (17) Å bonds are approximately equivalent and both are longer than the N2—C12 = 1.453 (16) Å bond. The indane (C12—C20) fused-ring system is nearly planar with a r.m.s deviation 0.0693 Å. The plane through the two fused rings of the indane system is slightly folded around the C14—C15 bond, as indicated by the dihedral angle between them of 5.20 (1)°. The dihedral angle between the mean plane of the pyrrolizine and indane system is 82.58 (1)°, indicating that they are nearly perpendicular to each other. The cyclopentane ring adopts a twisted conformation with puckering parameters: q₂ = 0.4839 (16) Å and Φ₂ = 17.98 (17)°. The dihedral angle between the mean planes of the pyrrolizine ring system and cyclopentane ring is 58.90 (1)°, indicating the significant curvature between the pyrrolizine and cyclopentene ring systems. The hydroxyl oxygen (O1) attached to the cyclopentane ring deviates by 1.1990 (10) Å from the mean plane of the ring. The piperidine ring with the methyl substituent in an equatorial position, adopts a twisted chair conformation with atoms C2 and C5 deviating by -0.6623 (10) Å and 0.8578 (10) Å respectively, from the mean plane defined by other atoms. In the structure, the aryl ring is in equatorial position of the attached pyrrolidine ring, as indicated by the torsion angle C7—C21—C26—C27 = -178.5 (15)°. The structure features a weak intramolecular O—H···N interaction.

Related literature top

For the importance of pyrrazole derivatives, see: Mahajan et al. (1991); Katayama & Oshiyama (1997); Baraldi et al. (1998). For additional conformation analysis, see: Cremer & Pople (1975).

Experimental top

A mixture of 1-methyl-3-[E-(4-methylphenyl)methylidene]tetrahydro-2(1H)-pyridinone (1 mmol), ninhydrin (1 mmol) and proline (1 mmol) in methanol was refluxed for 3–4 h. After completion of the reaction, as indicated by TLC, the reaction mixture was poured into cold water. The solid precipitate obtained was filtered and dried. The product was purified by column chromatography using petroleum ether:ethylacetate mixture (90:10 v/v). Suitable crystals for the single-crystal-X-ray studies were obtained by recrystallizing the product from methanol. Yield: 63%, Melting point: 464–466 K.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (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, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing 20% probability displacement ellipsoids and the atom-numbering scheme. H-atoms are omitted for clarity.

14a-Hydroxy-12-methyl-10-(4-methylphenyl)-8,9,9a,10,12,13,14,14a-octahydro-10a,14-methano-5H-indeno[2',1':4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione top

Crystal data top

C₂₇H₂₈N₂O₃	F(000) = 912
M_r = 428.51	D_x = 1.268 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2000 reflections
a = 16.8684 (6) Å	θ = 2–31°
b = 8.3754 (3) Å	µ = 0.08 mm⁻¹
c = 15.9930 (6) Å	T = 293 K
β = 96.658 (1)°	Block, colourless
V = 2244.25 (14) Å³	0.21 × 0.19 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	6850 independent reflections
Radiation source: fine-focus sealed tube	4500 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 0 pixels mm^-1	θ_max = 30.6°, θ_min = 2.4°
ω and ϕ scans	h = −24→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
T_min = 0.967, T_max = 0.974	l = −22→22
28459 measured reflections

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) = 0.161	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0784P)² + 0.3451P] where P = (F_o² + 2F_c²)/3
6850 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₇H₂₈N₂O₃	V = 2244.25 (14) Å³
M_r = 428.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.8684 (6) Å	µ = 0.08 mm⁻¹
b = 8.3754 (3) Å	T = 293 K
c = 15.9930 (6) Å	0.21 × 0.19 × 0.18 mm
β = 96.658 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	6850 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4500 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.974	R_int = 0.030
28459 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.02	Δρ_max = 0.29 e Å⁻³
6850 reflections	Δρ_min = −0.18 e Å⁻³
291 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	0.16397 (13)	−0.0312 (2)	0.12713 (14)	0.0736 (6)
H1A	0.1240	−0.0997	0.0986	0.110*
H1B	0.1529	−0.0146	0.1840	0.110*
H1C	0.2155	−0.0800	0.1274	0.110*
C2	0.08361 (9)	0.1896 (2)	0.06440 (12)	0.0555 (4)
H2A	0.0618	0.2147	0.1164	0.067*
H2B	0.0488	0.1119	0.0338	0.067*
C3	0.08668 (8)	0.34102 (18)	0.01156 (11)	0.0523 (4)
H3	0.0337	0.3886	−0.0022	0.063*
C4	0.14397 (9)	0.45411 (17)	0.06160 (10)	0.0476 (3)
C5	0.22549 (7)	0.37463 (15)	0.06215 (8)	0.0365 (3)
C6	0.22196 (9)	0.23342 (17)	0.12322 (9)	0.0436 (3)
H6A	0.2738	0.1825	0.1337	0.052*
H6B	0.2064	0.2702	0.1765	0.052*
C7	0.29914 (8)	0.48839 (15)	0.07586 (8)	0.0381 (3)
H7	0.2795	0.5984	0.0765	0.046*
C8	0.33710 (8)	0.46387 (17)	−0.00551 (9)	0.0409 (3)
H8	0.3715	0.3694	0.0007	0.049*
C9	0.37893 (11)	0.5938 (2)	−0.04996 (10)	0.0579 (4)
H9A	0.4353	0.5990	−0.0294	0.069*
H9B	0.3548	0.6974	−0.0429	0.069*
C10	0.36594 (13)	0.5389 (2)	−0.14257 (11)	0.0689 (5)
H10A	0.3475	0.6271	−0.1790	0.083*
H10B	0.4153	0.4983	−0.1600	0.083*
C11	0.30260 (10)	0.4065 (2)	−0.14693 (10)	0.0544 (4)
H11A	0.2626	0.4204	−0.1951	0.065*
H11B	0.3265	0.3016	−0.1495	0.065*
C12	0.22046 (7)	0.31215 (15)	−0.03006 (8)	0.0360 (3)
C13	0.13045 (8)	0.31994 (16)	−0.06716 (10)	0.0452 (3)
C14	0.11636 (8)	0.16665 (17)	−0.11540 (9)	0.0448 (3)
C15	0.17990 (8)	0.06209 (17)	−0.09945 (9)	0.0438 (3)
C16	0.24466 (8)	0.13717 (16)	−0.04209 (9)	0.0396 (3)
C17	0.17844 (10)	−0.0870 (2)	−0.13690 (12)	0.0576 (4)
H17	0.2205	−0.1583	−0.1247	0.069*
C18	0.11302 (11)	−0.1270 (2)	−0.19287 (13)	0.0681 (5)
H18	0.1113	−0.2261	−0.2193	0.082*
C19	0.05035 (11)	−0.0227 (2)	−0.21015 (12)	0.0659 (5)
H19	0.0073	−0.0514	−0.2489	0.079*
C20	0.05024 (10)	0.1241 (2)	−0.17081 (11)	0.0572 (4)
H20	0.0069	0.1928	−0.1812	0.069*
C21	0.35334 (8)	0.46023 (16)	0.15661 (8)	0.0386 (3)
C22	0.34229 (10)	0.54611 (18)	0.22797 (9)	0.0492 (4)
H22	0.3025	0.6233	0.2253	0.059*
C23	0.38944 (12)	0.5195 (2)	0.30366 (10)	0.0588 (4)
H23	0.3801	0.5786	0.3508	0.071*
C24	0.44955 (10)	0.4081 (2)	0.31081 (10)	0.0544 (4)
C25	0.46025 (10)	0.3211 (2)	0.24003 (11)	0.0595 (4)
H25	0.5002	0.2440	0.2430	0.071*
C26	0.41302 (10)	0.3457 (2)	0.16452 (10)	0.0554 (4)
H26	0.4215	0.2841	0.1180	0.066*
C27	0.50107 (14)	0.3797 (3)	0.39303 (13)	0.0907 (7)
H27A	0.5197	0.2713	0.3952	0.136*
H27B	0.4704	0.3987	0.4390	0.136*
H27C	0.5459	0.4510	0.3973	0.136*
N1	0.16329 (7)	0.12170 (14)	0.08371 (8)	0.0466 (3)
N2	0.26863 (7)	0.42998 (14)	−0.06780 (7)	0.0412 (3)
O1	0.11417 (7)	0.45503 (13)	−0.11974 (9)	0.0661 (4)
H1	0.1531	0.5144	−0.1152	0.099*
O2	0.30850 (6)	0.07901 (13)	−0.01635 (7)	0.0495 (3)
O3	0.12969 (7)	0.57851 (14)	0.09413 (9)	0.0683 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0835 (13)	0.0447 (9)	0.0899 (14)	−0.0161 (9)	−0.0015 (11)	0.0194 (9)
C2	0.0445 (8)	0.0507 (9)	0.0722 (11)	−0.0076 (7)	0.0108 (7)	0.0000 (8)
C3	0.0346 (6)	0.0406 (8)	0.0802 (11)	0.0045 (6)	0.0001 (7)	−0.0030 (7)
C4	0.0462 (7)	0.0355 (7)	0.0611 (9)	0.0035 (6)	0.0065 (7)	0.0001 (6)
C5	0.0383 (6)	0.0290 (6)	0.0413 (7)	−0.0008 (5)	0.0010 (5)	−0.0004 (5)
C6	0.0487 (7)	0.0373 (7)	0.0440 (7)	−0.0039 (6)	0.0026 (6)	0.0042 (6)
C7	0.0417 (6)	0.0314 (6)	0.0398 (7)	−0.0031 (5)	−0.0011 (5)	−0.0006 (5)
C8	0.0429 (7)	0.0407 (7)	0.0374 (7)	−0.0081 (5)	−0.0024 (5)	0.0013 (5)
C9	0.0632 (10)	0.0599 (10)	0.0499 (9)	−0.0257 (8)	0.0036 (7)	0.0054 (7)
C10	0.0879 (13)	0.0713 (12)	0.0489 (10)	−0.0298 (10)	0.0138 (9)	0.0033 (8)
C11	0.0668 (10)	0.0559 (9)	0.0396 (8)	−0.0119 (8)	0.0028 (7)	0.0005 (7)
C12	0.0364 (6)	0.0301 (6)	0.0396 (7)	−0.0022 (5)	−0.0043 (5)	0.0025 (5)
C13	0.0396 (7)	0.0326 (6)	0.0592 (9)	0.0005 (5)	−0.0119 (6)	0.0076 (6)
C14	0.0448 (7)	0.0394 (7)	0.0471 (8)	−0.0074 (6)	−0.0087 (6)	0.0053 (6)
C15	0.0438 (7)	0.0394 (7)	0.0462 (8)	−0.0046 (6)	−0.0037 (6)	−0.0021 (6)
C16	0.0408 (7)	0.0359 (7)	0.0405 (7)	−0.0012 (5)	−0.0019 (5)	−0.0007 (5)
C17	0.0548 (9)	0.0479 (9)	0.0674 (11)	−0.0029 (7)	−0.0046 (8)	−0.0152 (8)
C18	0.0704 (11)	0.0599 (11)	0.0704 (12)	−0.0127 (9)	−0.0077 (9)	−0.0229 (9)
C19	0.0642 (10)	0.0682 (12)	0.0593 (10)	−0.0210 (9)	−0.0177 (8)	−0.0066 (9)
C20	0.0521 (8)	0.0527 (9)	0.0608 (10)	−0.0091 (7)	−0.0187 (7)	0.0091 (8)
C21	0.0394 (6)	0.0376 (7)	0.0382 (7)	−0.0056 (5)	0.0023 (5)	−0.0020 (5)
C22	0.0598 (9)	0.0427 (8)	0.0446 (8)	0.0016 (7)	0.0035 (7)	−0.0055 (6)
C23	0.0833 (12)	0.0543 (9)	0.0377 (8)	−0.0053 (9)	0.0018 (8)	−0.0079 (7)
C24	0.0524 (8)	0.0644 (10)	0.0436 (8)	−0.0118 (8)	−0.0058 (7)	0.0055 (7)
C25	0.0476 (8)	0.0773 (12)	0.0526 (9)	0.0129 (8)	0.0014 (7)	0.0074 (8)
C26	0.0552 (9)	0.0691 (11)	0.0412 (8)	0.0156 (8)	0.0027 (7)	−0.0045 (7)
C27	0.0929 (15)	0.1150 (19)	0.0560 (12)	−0.0076 (14)	−0.0256 (11)	0.0093 (12)
N1	0.0495 (7)	0.0351 (6)	0.0547 (7)	−0.0066 (5)	0.0038 (6)	0.0059 (5)
N2	0.0464 (6)	0.0390 (6)	0.0364 (6)	−0.0089 (5)	−0.0027 (5)	0.0026 (5)
O1	0.0616 (7)	0.0435 (6)	0.0851 (9)	−0.0024 (5)	−0.0266 (6)	0.0229 (6)
O2	0.0404 (5)	0.0462 (6)	0.0591 (6)	0.0073 (4)	−0.0057 (5)	−0.0043 (5)
O3	0.0640 (7)	0.0453 (6)	0.0966 (10)	0.0087 (5)	0.0137 (7)	−0.0168 (6)

Geometric parameters (Å, º) top

C1—N1	1.456 (2)	C11—H11B	0.9700
C1—H1A	0.9600	C12—N2	1.4533 (17)
C1—H1B	0.9600	C12—C16	1.5394 (18)
C1—H1C	0.9600	C12—C13	1.5661 (18)
C2—N1	1.459 (2)	C13—O1	1.4174 (17)
C2—C3	1.528 (2)	C13—C14	1.503 (2)
C2—H2A	0.9700	C14—C15	1.385 (2)
C2—H2B	0.9700	C14—C20	1.3881 (19)
C3—C4	1.514 (2)	C15—C17	1.384 (2)
C3—C13	1.542 (2)	C15—C16	1.4825 (19)
C3—H3	0.9800	C16—O2	1.2098 (16)
C4—O3	1.2014 (18)	C17—C18	1.379 (2)
C4—C5	1.5269 (19)	C17—H17	0.9300
C5—C6	1.5394 (18)	C18—C19	1.375 (3)
C5—C12	1.5578 (18)	C18—H18	0.9300
C5—C7	1.5608 (17)	C19—C20	1.382 (3)
C6—N1	1.4524 (18)	C19—H19	0.9300
C6—H6A	0.9700	C20—H20	0.9300
C6—H6B	0.9700	C21—C22	1.380 (2)
C7—C21	1.5118 (18)	C21—C26	1.385 (2)
C7—C8	1.5293 (19)	C22—C23	1.387 (2)
C7—H7	0.9800	C22—H22	0.9300
C8—N2	1.4629 (17)	C23—C24	1.373 (3)
C8—C9	1.518 (2)	C23—H23	0.9300
C8—H8	0.9800	C24—C25	1.375 (2)
C9—C10	1.542 (2)	C24—C27	1.509 (2)
C9—H9A	0.9700	C25—C26	1.383 (2)
C9—H9B	0.9700	C25—H25	0.9300
C10—C11	1.536 (2)	C26—H26	0.9300
C10—H10A	0.9700	C27—H27A	0.9600
C10—H10B	0.9700	C27—H27B	0.9600
C11—N2	1.462 (2)	C27—H27C	0.9600
C11—H11A	0.9700	O1—H1	0.8200

N1—C1—H1A	109.5	N2—C12—C5	101.15 (10)
N1—C1—H1B	109.5	C16—C12—C5	116.87 (11)
H1A—C1—H1B	109.5	N2—C12—C13	112.24 (10)
N1—C1—H1C	109.5	C16—C12—C13	104.58 (10)
H1A—C1—H1C	109.5	C5—C12—C13	106.78 (11)
H1B—C1—H1C	109.5	O1—C13—C14	111.67 (12)
N1—C2—C3	110.55 (12)	O1—C13—C3	108.35 (12)
N1—C2—H2A	109.5	C14—C13—C3	117.05 (12)
C3—C2—H2A	109.5	O1—C13—C12	111.76 (11)
N1—C2—H2B	109.5	C14—C13—C12	104.34 (11)
C3—C2—H2B	109.5	C3—C13—C12	103.32 (11)
H2A—C2—H2B	108.1	C15—C14—C20	120.18 (14)
C4—C3—C2	106.70 (13)	C15—C14—C13	111.89 (11)
C4—C3—C13	99.58 (12)	C20—C14—C13	127.93 (14)
C2—C3—C13	113.99 (12)	C17—C15—C14	121.09 (13)
C4—C3—H3	111.9	C17—C15—C16	128.71 (14)
C2—C3—H3	111.9	C14—C15—C16	110.17 (12)
C13—C3—H3	111.9	O2—C16—C15	127.06 (13)
O3—C4—C3	128.58 (14)	O2—C16—C12	125.40 (12)
O3—C4—C5	126.97 (14)	C15—C16—C12	107.10 (11)
C3—C4—C5	104.45 (11)	C18—C17—C15	118.22 (16)
C4—C5—C6	103.74 (11)	C18—C17—H17	120.9
C4—C5—C12	101.00 (11)	C15—C17—H17	120.9
C6—C5—C12	109.92 (10)	C19—C18—C17	120.98 (17)
C4—C5—C7	115.87 (11)	C19—C18—H18	119.5
C6—C5—C7	117.94 (11)	C17—C18—H18	119.5
C12—C5—C7	107.05 (10)	C18—C19—C20	121.05 (15)
N1—C6—C5	107.06 (11)	C18—C19—H19	119.5
N1—C6—H6A	110.3	C20—C19—H19	119.5
C5—C6—H6A	110.3	C19—C20—C14	118.41 (16)
N1—C6—H6B	110.3	C19—C20—H20	120.8
C5—C6—H6B	110.3	C14—C20—H20	120.8
H6A—C6—H6B	108.6	C22—C21—C26	116.85 (13)
C21—C7—C8	115.76 (11)	C22—C21—C7	119.93 (13)
C21—C7—C5	114.67 (11)	C26—C21—C7	123.17 (13)
C8—C7—C5	101.74 (10)	C21—C22—C23	121.27 (15)
C21—C7—H7	108.1	C21—C22—H22	119.4
C8—C7—H7	108.1	C23—C22—H22	119.4
C5—C7—H7	108.1	C24—C23—C22	121.68 (15)
N2—C8—C9	101.15 (11)	C24—C23—H23	119.2
N2—C8—C7	103.31 (11)	C22—C23—H23	119.2
C9—C8—C7	124.43 (13)	C23—C24—C25	117.22 (15)
N2—C8—H8	108.9	C23—C24—C27	121.66 (18)
C9—C8—H8	108.9	C25—C24—C27	121.11 (18)
C7—C8—H8	108.9	C24—C25—C26	121.50 (16)
C8—C9—C10	102.34 (12)	C24—C25—H25	119.3
C8—C9—H9A	111.3	C26—C25—H25	119.3
C10—C9—H9A	111.3	C25—C26—C21	121.46 (15)
C8—C9—H9B	111.3	C25—C26—H26	119.3
C10—C9—H9B	111.3	C21—C26—H26	119.3
H9A—C9—H9B	109.2	C24—C27—H27A	109.5
C11—C10—C9	106.25 (13)	C24—C27—H27B	109.5
C11—C10—H10A	110.5	H27A—C27—H27B	109.5
C9—C10—H10A	110.5	C24—C27—H27C	109.5
C11—C10—H10B	110.5	H27A—C27—H27C	109.5
C9—C10—H10B	110.5	H27B—C27—H27C	109.5
H10A—C10—H10B	108.7	C6—N1—C1	113.06 (13)
N2—C11—C10	101.77 (12)	C6—N1—C2	113.93 (12)
N2—C11—H11A	111.4	C1—N1—C2	113.56 (13)
C10—C11—H11A	111.4	C12—N2—C11	124.22 (11)
N2—C11—H11B	111.4	C12—N2—C8	106.51 (10)
C10—C11—H11B	111.4	C11—N2—C8	104.95 (11)
H11A—C11—H11B	109.3	C13—O1—H1	109.5
N2—C12—C16	115.18 (11)

N1—C2—C3—C4	−57.27 (17)	C12—C13—C14—C15	10.41 (16)
N1—C2—C3—C13	51.62 (18)	O1—C13—C14—C20	−48.4 (2)
C2—C3—C4—O3	−111.93 (19)	C3—C13—C14—C20	77.3 (2)
C13—C3—C4—O3	129.31 (18)	C12—C13—C14—C20	−169.26 (15)
C2—C3—C4—C5	67.92 (15)	C20—C14—C15—C17	−1.1 (2)
C13—C3—C4—C5	−50.84 (14)	C13—C14—C15—C17	179.19 (15)
O3—C4—C5—C6	106.79 (18)	C20—C14—C15—C16	177.07 (14)
C3—C4—C5—C6	−73.07 (14)	C13—C14—C15—C16	−2.63 (18)
O3—C4—C5—C12	−139.33 (17)	C17—C15—C16—O2	−1.3 (3)
C3—C4—C5—C12	40.81 (14)	C14—C15—C16—O2	−179.28 (14)
O3—C4—C5—C7	−24.1 (2)	C17—C15—C16—C12	171.45 (16)
C3—C4—C5—C7	156.03 (12)	C14—C15—C16—C12	−6.55 (16)
C4—C5—C6—N1	67.25 (14)	N2—C12—C16—O2	61.65 (19)
C12—C5—C6—N1	−40.06 (14)	C5—C12—C16—O2	−56.89 (19)
C7—C5—C6—N1	−163.10 (11)	C13—C12—C16—O2	−174.68 (14)
C4—C5—C7—C21	115.03 (14)	N2—C12—C16—C15	−111.23 (12)
C6—C5—C7—C21	−8.76 (17)	C5—C12—C16—C15	130.23 (12)
C12—C5—C7—C21	−133.23 (11)	C13—C12—C16—C15	12.44 (14)
C4—C5—C7—C8	−119.25 (13)	C14—C15—C17—C18	2.1 (3)
C6—C5—C7—C8	116.97 (13)	C16—C15—C17—C18	−175.70 (16)
C12—C5—C7—C8	−7.51 (13)	C15—C17—C18—C19	−0.9 (3)
C21—C7—C8—N2	156.36 (11)	C17—C18—C19—C20	−1.3 (3)
C5—C7—C8—N2	31.36 (12)	C18—C19—C20—C14	2.3 (3)
C21—C7—C8—C9	−89.87 (17)	C15—C14—C20—C19	−1.1 (2)
C5—C7—C8—C9	145.12 (13)	C13—C14—C20—C19	178.57 (16)
N2—C8—C9—C10	−36.92 (17)	C8—C7—C21—C22	148.72 (13)
C7—C8—C9—C10	−151.73 (15)	C5—C7—C21—C22	−93.23 (15)
C8—C9—C10—C11	12.7 (2)	C8—C7—C21—C26	−34.09 (19)
C9—C10—C11—N2	16.2 (2)	C5—C7—C21—C26	83.96 (17)
C4—C5—C12—N2	102.67 (11)	C26—C21—C22—C23	0.6 (2)
C6—C5—C12—N2	−148.20 (11)	C7—C21—C22—C23	177.97 (14)
C7—C5—C12—N2	−18.97 (12)	C21—C22—C23—C24	0.7 (3)
C4—C5—C12—C16	−131.46 (12)	C22—C23—C24—C25	−1.3 (3)
C6—C5—C12—C16	−22.32 (15)	C22—C23—C24—C27	179.71 (18)
C7—C5—C12—C16	106.91 (12)	C23—C24—C25—C26	0.6 (3)
C4—C5—C12—C13	−14.88 (12)	C27—C24—C25—C26	179.64 (19)
C6—C5—C12—C13	94.26 (12)	C24—C25—C26—C21	0.7 (3)
C7—C5—C12—C13	−136.51 (10)	C22—C21—C26—C25	−1.3 (2)
C4—C3—C13—O1	−79.52 (13)	C7—C21—C26—C25	−178.53 (15)
C2—C3—C13—O1	167.27 (12)	C5—C6—N1—C1	169.39 (14)
C4—C3—C13—C14	153.16 (12)	C5—C6—N1—C2	−58.99 (16)
C2—C3—C13—C14	39.95 (17)	C3—C2—N1—C6	54.13 (18)
C4—C3—C13—C12	39.16 (13)	C3—C2—N1—C1	−174.49 (15)
C2—C3—C13—C12	−74.05 (14)	C16—C12—N2—C11	35.17 (18)
N2—C12—C13—O1	−8.82 (17)	C5—C12—N2—C11	162.16 (13)
C16—C12—C13—O1	−134.36 (13)	C13—C12—N2—C11	−84.36 (16)
C5—C12—C13—O1	101.15 (14)	C16—C12—N2—C8	−86.64 (13)
N2—C12—C13—C14	112.01 (12)	C5—C12—N2—C8	40.35 (13)
C16—C12—C13—C14	−13.54 (14)	C13—C12—N2—C8	153.84 (12)
C5—C12—C13—C14	−138.02 (11)	C10—C11—N2—C12	−163.50 (14)
N2—C12—C13—C3	−125.10 (12)	C10—C11—N2—C8	−40.99 (16)
C16—C12—C13—C3	109.35 (12)	C9—C8—N2—C12	−176.64 (12)
C5—C12—C13—C3	−15.13 (13)	C7—C8—N2—C12	−46.94 (13)
O1—C13—C14—C15	131.29 (14)	C9—C8—N2—C11	50.03 (15)
C3—C13—C14—C15	−103.02 (15)	C7—C8—N2—C11	179.73 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	2.13	2.6497 (16)	121
C19—H19···O1ⁱ	0.93	2.76	3.659 (2)	163

Symmetry code: (i) −x, y−1/2, −z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	2.13	2.6497 (16)	121
C19—H19···O1ⁱ	0.93	2.76	3.659 (2)	163

Symmetry code: (i) −x, y−1/2, −z−1/2.

Acknowledgements

JS and RAN thank the management of Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (No. SR/FT/CS-073/2009).

References

Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165–2171. Web of Science CrossRef CAS Google Scholar
Bruker (2004). APEX2 and SAINT. 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
Katayama, H. & Oshiyama, T. (1997). Can. J. Chem. 75, 913–919. CrossRef CAS Web of Science Google Scholar
Mahajan, R. N., Havaldar, F. H. & Fernandes, P. S. (1991). J. Indian Chem. Soc. 68, 245–249. 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. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

14a-Hy­dr­oxy-12-methyl-10-(4-methyl­phen­yl)-8,9,9a,10,12,13,14,14a-octa­hydro-10a,14-methano-5H-indeno­[2′,1′:4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione

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Experimental

Crystal data

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organic compounds

14a-Hydroxy-12-methyl-10-(4-methylphenyl)-8,9,9a,10,12,13,14,14a-octahydro-10a,14-methano-5H-indeno[2′,1′:4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione