Methyl 1-methyl-3-p-tolyl-1,2,3,3a,4,11c-hexa­hydro­benzo[f]chromeno[4,3-b]pyrrole-3a-carboxyl­ate

Nirmala, S.; Kamala, E.T.S.; Sudha, L.; Kathiravan, S.; Raghunathan, R.

doi:10.1107/S1600536809024738

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1811

doi:10.1107/S1600536809024738

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Methyl 1-methyl-3-p-tolyl-1,2,3,3a,4,11c-hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate

S. Nirmala,^a E. Theboral Sugi Kamala,^a L. Sudha,^b ^* S. Kathiravan ^c and R. Raghunathan ^c

^aDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India, ^bDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: sudharose18@gmail.com

(Received 5 June 2009; accepted 26 June 2009; online 11 July 2009)

In the title compound, C₂₅H₂₅NO₃, the dihydropyran ring adopts a half-chair conformation, whereas the pyrrolidine ring is in a twist conformation. The tolyl group is oriented at an angle of 82.92 (7)° with respect to the napthalene ring system. In the crystal structure, molecules are linked into centrosymmetric dimers by C—H⋯π interactions involving the benzene ring of the tolyl group.

Related literature

For the biological activity of pyrrole derivatives, see: Biava et al. (2005 ); Borthwick et al. (2000 ); Caine (1993 ); Carlson (1993 ); Fernandes et al. (2004 ); Jiang et al. (2004 ); Sokoloff et al. (1990 ); Tidey & Miczek (1992 ); Wilner (1985 ). For a related structure, see: Gunasekaran et al. (2009 ). For ring-puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₅H₂₅NO₃
M_r = 387.46
Monoclinic, P 2₁ /n
a = 12.9899 (6) Å
b = 7.6751 (3) Å
c = 20.5073 (9) Å
β = 96.881 (2)°
V = 2029.83 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa-APEXII area-detector diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.980, T_max = 0.984
22975 measured reflections
4790 independent reflections
3176 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.156
S = 1.05
4790 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22A⋯Cg1ⁱ	0.96	2.84	3.788 (2)	169
Symmetry code: (i) -x, -y+1, -z+1. Cg1 is the centroid of the C16–C21 ring.

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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024738/ci2823sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024738/ci2823Isup2.hkl

checkCIF report

Comment top

Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993), aggressiveness (Tidey & Miczek, 1992), parkinson's disease (Carlson, 1993), psychoses, memory disorders (Sokoloff et al., 1990), anxiety and depression (Wilner, 1985). Pyrrole derivatives have good in vitro activities against mycobacteria and candidae (Biava et al., 2005). These derivatives also possess anti-inflammatory (Fernandes et al., 2004) and antiviral (Borthwick et al., 2000) activities. It has also been shown that N–substituted pyrrole derivatives inhibit human immuno deficiency virus type-I (HIV-I) (Jiang et al., 2004). In view of its medicinal importance, the crystal structure determination of the title compound was undertaken.

The geometric parameters of the title molecule (Fig. 1) agree well with those reported for a similar structure (Gunasekaran et al., 2009). The sum of bond angles around atom N1 (334.0°) is in accordance with sp³ hybridization. The napthalene ring system (C2-C11) and the tolyl group (C16-C22) are oriented at an angle of 82.92 (7)° with respect to each other. The heterocyclic ring (O1/C1/C2/C11-C13) of the chromenopyrrole unit adopts a half-chair conformation, with puckering parameters Q = 0.462 (2) Å, θ = 49.3 (2)° and ϕ = 261.2 (2)° (Cremer and Pople, 1975). The pyrrolidine ring (N1/C1/C13-C15) adopts a twist conformation, with puckering parameters of q₂ = 0.485 (1) Å and ϕ = 16.2 (2)° (Cremer and Pople, 1975).

The crystal packing is stabilized by weak intermolecular C—H···π [C22—H22A···Cg1; Cg1 is the centroid of the C16—C21 ring] interactions (Table 1).

Related literature top

For biological activity of pyrrole derivatives, see: Biava et al. (2005); Borthwick et al. (2000); Caine (1993); Carlson (1993); Fernandes et al. (2004); Jiang et al. (2004); Sokoloff et al. (1990); Tidey & Miczek (1992); Wilner (1985). For a related structure, see: Gunasekaran et al. (2009). For ring-puckering parameters, see: Cremer & Pople (1975). Cg1 is the centroid of the C16–C21 ring.

Experimental top

A mixture of (Z)-methyl 2-((1-formylnaphthalen-2-yloxy)methyl)-3- p-tolylacrylate (20 mmol) and sarcosine (30 mmol) was refluxed in benzene for 20 h and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to get the pure product. A chloroform and methanol (1:1) solvent mixture was used for the crystallization under slow evaporation method.

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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with 30% probability displacement ellipsoids.
	Fig. 2. The packing of the molecules viewed down the a axis. H atoms not involed in C—H···π interactions (dashed lines) have been omitted.

Methyl 1-methyl-3-p-tolyl-1,2,3,3a,4,11c- hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate top

Crystal data top

C₂₅H₂₅NO₃	F(000) = 824
M_r = 387.46	D_x = 1.268 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6463 reflections
a = 12.9899 (6) Å	θ = 2.8–25.6°
b = 7.6751 (3) Å	µ = 0.08 mm⁻¹
c = 20.5073 (9) Å	T = 293 K
β = 96.881 (2)°	Prism, colourless
V = 2029.83 (15) Å³	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa-APEXII area-detector diffractometer	4790 independent reflections
Radiation source: fine-focus sealed tube	3176 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and ϕ scans	θ_max = 27.8°, θ_min = 1.8°
Absorption correction: multi-scan (Blessing, 1995)	h = −17→16
T_min = 0.980, T_max = 0.984	k = −8→10
22975 measured reflections	l = −20→26

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.081P)² + 0.2107P] where P = (F_o² + 2F_c²)/3
4790 reflections	(Δ/σ)_max = 0.001
265 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₅H₂₅NO₃	V = 2029.83 (15) Å³
M_r = 387.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.9899 (6) Å	µ = 0.08 mm⁻¹
b = 7.6751 (3) Å	T = 293 K
c = 20.5073 (9) Å	0.25 × 0.20 × 0.20 mm
β = 96.881 (2)°

Data collection top

Bruker Kappa-APEXII area-detector diffractometer	4790 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	3176 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.984	R_int = 0.028
22975 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
4790 reflections	Δρ_min = −0.19 e Å⁻³
265 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	−0.09259 (11)	0.31953 (19)	0.17432 (7)	0.0388 (3)
H1	−0.0790	0.2192	0.1471	0.047*
C2	−0.08470 (10)	0.48434 (19)	0.13573 (7)	0.0384 (3)
C3	−0.11550 (11)	0.4919 (2)	0.06634 (7)	0.0446 (4)
C4	−0.15523 (13)	0.3466 (3)	0.02933 (8)	0.0558 (4)
H4	−0.1621	0.2406	0.0503	0.067*
C5	−0.18383 (15)	0.3592 (3)	−0.03703 (9)	0.0697 (6)
H5	−0.2104	0.2622	−0.0605	0.084*
C6	−0.17327 (16)	0.5168 (4)	−0.06962 (10)	0.0765 (6)
H6	−0.1929	0.5245	−0.1147	0.092*
C7	−0.13492 (15)	0.6571 (3)	−0.03608 (9)	0.0681 (6)
H7	−0.1283	0.7612	−0.0584	0.082*
C8	−0.10438 (12)	0.6502 (2)	0.03225 (8)	0.0527 (4)
C9	−0.06138 (14)	0.7959 (2)	0.06742 (9)	0.0569 (5)
H9	−0.0551	0.9007	0.0454	0.068*
C10	−0.02925 (12)	0.7865 (2)	0.13232 (9)	0.0499 (4)
H10	−0.0001	0.8835	0.1546	0.060*
C11	−0.04003 (11)	0.6293 (2)	0.16629 (7)	0.0412 (4)
C12	−0.02357 (12)	0.4915 (2)	0.27124 (7)	0.0421 (4)
H12A	−0.0931	0.5077	0.2830	0.051*
H12B	0.0241	0.4923	0.3115	0.051*
C13	−0.01754 (11)	0.31594 (19)	0.23809 (7)	0.0383 (3)
C14	−0.06451 (12)	0.1678 (2)	0.27941 (8)	0.0460 (4)
H14	−0.0239	0.0616	0.2752	0.055*
C15	−0.17243 (13)	0.1390 (2)	0.24138 (8)	0.0541 (4)
H15A	−0.1732	0.0353	0.2143	0.065*
H15B	−0.2245	0.1268	0.2713	0.065*
C16	−0.06274 (12)	0.2062 (2)	0.35187 (8)	0.0452 (4)
C17	0.02402 (13)	0.1666 (2)	0.39539 (9)	0.0560 (5)
H17	0.0815	0.1176	0.3794	0.067*
C18	0.02723 (15)	0.1980 (3)	0.46167 (10)	0.0649 (5)
H18	0.0867	0.1691	0.4895	0.078*
C19	−0.05580 (15)	0.2713 (2)	0.48788 (8)	0.0584 (5)
C20	−0.14203 (14)	0.3124 (2)	0.44449 (9)	0.0579 (5)
H20	−0.1991	0.3631	0.4604	0.070*
C21	−0.14554 (13)	0.2801 (2)	0.37841 (9)	0.0537 (4)
H21	−0.2052	0.3086	0.3507	0.064*
C22	−0.0533 (2)	0.3059 (3)	0.56044 (9)	0.0838 (7)
H22A	−0.0196	0.4154	0.5711	0.126*
H22B	−0.0157	0.2144	0.5848	0.126*
H22C	−0.1229	0.3100	0.5717	0.126*
C23	−0.28437 (12)	0.2833 (2)	0.15488 (9)	0.0548 (4)
H23A	−0.2814	0.1813	0.1281	0.082*
H23B	−0.2897	0.3850	0.1275	0.082*
H23C	−0.3438	0.2763	0.1784	0.082*
C24	0.09063 (12)	0.2649 (2)	0.22557 (8)	0.0416 (4)
C25	0.26911 (14)	0.2845 (3)	0.26242 (13)	0.0781 (6)
H25A	0.2773	0.1627	0.2723	0.117*
H25B	0.3156	0.3507	0.2929	0.117*
H25C	0.2847	0.3057	0.2185	0.117*
N1	−0.19140 (9)	0.29402 (17)	0.20102 (6)	0.0447 (3)
O1	0.00093 (8)	0.63413 (14)	0.23080 (5)	0.0468 (3)
O2	0.16331 (8)	0.33635 (16)	0.26780 (7)	0.0646 (4)
O3	0.10931 (9)	0.16459 (17)	0.18379 (6)	0.0630 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0344 (7)	0.0380 (8)	0.0430 (8)	−0.0011 (6)	0.0001 (6)	−0.0058 (7)
C2	0.0304 (7)	0.0415 (8)	0.0431 (8)	0.0015 (6)	0.0038 (6)	0.0003 (7)
C3	0.0321 (7)	0.0576 (10)	0.0441 (8)	0.0046 (7)	0.0051 (6)	−0.0006 (8)
C4	0.0458 (9)	0.0734 (12)	0.0471 (9)	−0.0008 (8)	0.0007 (7)	−0.0069 (9)
C5	0.0537 (11)	0.1041 (17)	0.0497 (10)	−0.0019 (10)	−0.0004 (8)	−0.0152 (12)
C6	0.0628 (12)	0.123 (2)	0.0424 (10)	0.0045 (12)	0.0015 (9)	0.0075 (13)
C7	0.0589 (11)	0.0952 (16)	0.0508 (11)	0.0062 (11)	0.0099 (9)	0.0179 (11)
C8	0.0393 (8)	0.0695 (12)	0.0498 (9)	0.0082 (8)	0.0079 (7)	0.0100 (9)
C9	0.0514 (10)	0.0550 (10)	0.0657 (12)	0.0057 (8)	0.0125 (9)	0.0172 (9)
C10	0.0451 (9)	0.0411 (9)	0.0641 (11)	0.0012 (7)	0.0087 (8)	0.0018 (8)
C11	0.0346 (7)	0.0417 (8)	0.0475 (9)	0.0029 (6)	0.0060 (6)	0.0003 (7)
C12	0.0416 (8)	0.0425 (8)	0.0412 (8)	−0.0030 (6)	0.0009 (6)	−0.0026 (7)
C13	0.0356 (7)	0.0374 (8)	0.0405 (8)	−0.0027 (6)	−0.0004 (6)	−0.0008 (7)
C14	0.0456 (9)	0.0403 (8)	0.0514 (9)	−0.0048 (6)	0.0026 (7)	0.0029 (7)
C15	0.0522 (10)	0.0549 (10)	0.0532 (10)	−0.0157 (8)	−0.0020 (8)	0.0042 (8)
C16	0.0408 (8)	0.0444 (9)	0.0492 (9)	−0.0051 (7)	0.0006 (7)	0.0091 (7)
C17	0.0427 (9)	0.0659 (11)	0.0578 (11)	0.0057 (8)	0.0004 (8)	0.0116 (9)
C18	0.0535 (11)	0.0802 (13)	0.0570 (11)	−0.0022 (9)	−0.0100 (8)	0.0153 (10)
C19	0.0630 (11)	0.0621 (11)	0.0489 (10)	−0.0158 (9)	0.0020 (9)	0.0107 (9)
C20	0.0515 (10)	0.0659 (11)	0.0578 (11)	−0.0034 (8)	0.0123 (8)	0.0048 (9)
C21	0.0420 (9)	0.0638 (11)	0.0535 (10)	0.0009 (8)	−0.0013 (7)	0.0090 (9)
C22	0.1037 (18)	0.0954 (17)	0.0512 (11)	−0.0230 (14)	0.0053 (11)	0.0049 (11)
C23	0.0395 (9)	0.0615 (11)	0.0613 (10)	−0.0084 (7)	−0.0022 (8)	−0.0030 (9)
C24	0.0399 (8)	0.0368 (8)	0.0468 (9)	−0.0003 (6)	−0.0005 (7)	0.0044 (7)
C25	0.0356 (10)	0.0670 (13)	0.1270 (19)	0.0046 (8)	−0.0098 (10)	−0.0069 (12)
N1	0.0348 (7)	0.0491 (8)	0.0489 (7)	−0.0082 (5)	−0.0005 (5)	−0.0006 (6)
O1	0.0517 (6)	0.0394 (6)	0.0475 (6)	−0.0069 (5)	−0.0009 (5)	−0.0037 (5)
O2	0.0366 (6)	0.0623 (8)	0.0905 (9)	0.0003 (5)	−0.0102 (6)	−0.0199 (7)
O3	0.0515 (7)	0.0710 (8)	0.0657 (8)	0.0128 (6)	0.0039 (6)	−0.0153 (7)

Geometric parameters (Å, º) top

C1—N1	1.4676 (18)	C14—C15	1.536 (2)
C1—C2	1.502 (2)	C14—H14	0.98
C1—C13	1.5348 (19)	C15—N1	1.454 (2)
C1—H1	0.98	C15—H15A	0.97
C2—C11	1.371 (2)	C15—H15B	0.97
C2—C3	1.432 (2)	C16—C21	1.384 (2)
C3—C4	1.411 (2)	C16—C17	1.385 (2)
C3—C8	1.418 (2)	C17—C18	1.376 (3)
C4—C5	1.370 (2)	C17—H17	0.93
C4—H4	0.93	C18—C19	1.381 (3)
C5—C6	1.397 (3)	C18—H18	0.93
C5—H5	0.93	C19—C20	1.381 (3)
C6—C7	1.341 (3)	C19—C22	1.508 (3)
C6—H6	0.93	C20—C21	1.373 (2)
C7—C8	1.411 (3)	C20—H20	0.93
C7—H7	0.93	C21—H21	0.93
C8—C9	1.409 (3)	C22—H22A	0.96
C9—C10	1.348 (2)	C22—H22B	0.96
C9—H9	0.93	C22—H22C	0.96
C10—C11	1.409 (2)	C23—N1	1.4445 (19)
C10—H10	0.93	C23—H23A	0.96
C11—O1	1.3661 (18)	C23—H23B	0.96
C12—O1	1.4318 (18)	C23—H23C	0.96
C12—C13	1.516 (2)	C24—O3	1.1983 (19)
C12—H12A	0.97	C24—O2	1.3214 (19)
C12—H12B	0.97	C25—O2	1.448 (2)
C13—C24	1.510 (2)	C25—H25A	0.96
C13—C14	1.583 (2)	C25—H25B	0.96
C14—C16	1.512 (2)	C25—H25C	0.96

N1—C1—C2	115.26 (12)	C15—C14—H14	107.7
N1—C1—C13	100.04 (11)	C13—C14—H14	107.7
C2—C1—C13	112.81 (12)	N1—C15—C14	104.68 (12)
N1—C1—H1	109.4	N1—C15—H15A	110.8
C2—C1—H1	109.4	C14—C15—H15A	110.8
C13—C1—H1	109.4	N1—C15—H15B	110.8
C11—C2—C3	118.29 (14)	C14—C15—H15B	110.8
C11—C2—C1	119.61 (13)	H15A—C15—H15B	108.9
C3—C2—C1	121.93 (13)	C21—C16—C17	116.58 (15)
C4—C3—C8	117.66 (15)	C21—C16—C14	123.05 (14)
C4—C3—C2	122.89 (15)	C17—C16—C14	120.37 (15)
C8—C3—C2	119.44 (15)	C18—C17—C16	121.60 (17)
C5—C4—C3	121.10 (19)	C18—C17—H17	119.2
C5—C4—H4	119.5	C16—C17—H17	119.2
C3—C4—H4	119.5	C17—C18—C19	121.54 (17)
C4—C5—C6	120.4 (2)	C17—C18—H18	119.2
C4—C5—H5	119.8	C19—C18—H18	119.2
C6—C5—H5	119.8	C20—C19—C18	116.95 (17)
C7—C6—C5	120.10 (18)	C20—C19—C22	121.04 (19)
C7—C6—H6	119.9	C18—C19—C22	122.01 (19)
C5—C6—H6	119.9	C21—C20—C19	121.54 (17)
C6—C7—C8	121.5 (2)	C21—C20—H20	119.2
C6—C7—H7	119.2	C19—C20—H20	119.2
C8—C7—H7	119.2	C20—C21—C16	121.79 (16)
C9—C8—C7	121.71 (18)	C20—C21—H21	119.1
C9—C8—C3	119.04 (15)	C16—C21—H21	119.1
C7—C8—C3	119.24 (18)	C19—C22—H22A	109.5
C10—C9—C8	121.28 (16)	C19—C22—H22B	109.5
C10—C9—H9	119.4	H22A—C22—H22B	109.5
C8—C9—H9	119.4	C19—C22—H22C	109.5
C9—C10—C11	119.79 (16)	H22A—C22—H22C	109.5
C9—C10—H10	120.1	H22B—C22—H22C	109.5
C11—C10—H10	120.1	N1—C23—H23A	109.5
O1—C11—C2	124.01 (13)	N1—C23—H23B	109.5
O1—C11—C10	113.90 (13)	H23A—C23—H23B	109.5
C2—C11—C10	122.05 (14)	N1—C23—H23C	109.5
O1—C12—C13	113.13 (11)	H23A—C23—H23C	109.5
O1—C12—H12A	109.0	H23B—C23—H23C	109.5
C13—C12—H12A	109.0	O3—C24—O2	123.05 (15)
O1—C12—H12B	109.0	O3—C24—C13	124.09 (14)
C13—C12—H12B	109.0	O2—C24—C13	112.79 (14)
H12A—C12—H12B	107.8	O2—C25—H25A	109.5
C24—C13—C12	113.95 (12)	O2—C25—H25B	109.5
C24—C13—C1	111.64 (12)	H25A—C25—H25B	109.5
C12—C13—C1	107.73 (12)	O2—C25—H25C	109.5
C24—C13—C14	109.32 (12)	H25A—C25—H25C	109.5
C12—C13—C14	110.77 (12)	H25B—C25—H25C	109.5
C1—C13—C14	102.87 (11)	C23—N1—C15	113.43 (13)
C16—C14—C15	115.62 (14)	C23—N1—C1	117.60 (13)
C16—C14—C13	115.10 (12)	C15—N1—C1	103.03 (12)
C15—C14—C13	102.60 (12)	C11—O1—C12	116.89 (11)
C16—C14—H14	107.7	C24—O2—C25	116.50 (15)

N1—C1—C2—C11	94.97 (15)	C12—C13—C14—C16	−24.73 (17)
C13—C1—C2—C11	−19.09 (18)	C1—C13—C14—C16	−139.61 (13)
N1—C1—C2—C3	−89.82 (16)	C24—C13—C14—C15	−131.92 (14)
C13—C1—C2—C3	156.12 (13)	C12—C13—C14—C15	101.71 (14)
C11—C2—C3—C4	175.31 (14)	C1—C13—C14—C15	−13.17 (15)
C1—C2—C3—C4	0.0 (2)	C16—C14—C15—N1	108.16 (15)
C11—C2—C3—C8	−3.5 (2)	C13—C14—C15—N1	−17.95 (16)
C1—C2—C3—C8	−178.76 (13)	C15—C14—C16—C21	−25.5 (2)
C8—C3—C4—C5	−1.2 (2)	C13—C14—C16—C21	93.96 (18)
C2—C3—C4—C5	180.00 (15)	C15—C14—C16—C17	154.05 (15)
C3—C4—C5—C6	0.6 (3)	C13—C14—C16—C17	−86.49 (18)
C4—C5—C6—C7	0.0 (3)	C21—C16—C17—C18	0.5 (3)
C5—C6—C7—C8	0.0 (3)	C14—C16—C17—C18	−179.11 (16)
C6—C7—C8—C9	178.23 (18)	C16—C17—C18—C19	−0.3 (3)
C6—C7—C8—C3	−0.7 (3)	C17—C18—C19—C20	−0.2 (3)
C4—C3—C8—C9	−177.71 (15)	C17—C18—C19—C22	179.83 (19)
C2—C3—C8—C9	1.2 (2)	C18—C19—C20—C21	0.7 (3)
C4—C3—C8—C7	1.2 (2)	C22—C19—C20—C21	−179.40 (18)
C2—C3—C8—C7	−179.93 (14)	C19—C20—C21—C16	−0.5 (3)
C7—C8—C9—C10	−177.77 (16)	C17—C16—C21—C20	0.0 (3)
C3—C8—C9—C10	1.1 (2)	C14—C16—C21—C20	179.53 (16)
C8—C9—C10—C11	−1.0 (2)	C12—C13—C24—O3	−155.81 (15)
C3—C2—C11—O1	−173.98 (12)	C1—C13—C24—O3	−33.5 (2)
C1—C2—C11—O1	1.4 (2)	C14—C13—C24—O3	79.66 (18)
C3—C2—C11—C10	3.7 (2)	C12—C13—C24—O2	27.28 (18)
C1—C2—C11—C10	179.09 (13)	C1—C13—C24—O2	149.60 (13)
C9—C10—C11—O1	176.41 (14)	C14—C13—C24—O2	−97.25 (15)
C9—C10—C11—C2	−1.5 (2)	C14—C15—N1—C23	172.67 (14)
O1—C12—C13—C24	66.46 (16)	C14—C15—N1—C1	44.46 (15)
O1—C12—C13—C1	−57.99 (15)	C2—C1—N1—C23	60.86 (17)
O1—C12—C13—C14	−169.79 (11)	C13—C1—N1—C23	−177.89 (13)
N1—C1—C13—C24	156.25 (12)	C2—C1—N1—C15	−173.59 (12)
C2—C1—C13—C24	−80.75 (15)	C13—C1—N1—C15	−52.33 (13)
N1—C1—C13—C12	−77.92 (13)	C2—C11—O1—C12	−13.3 (2)
C2—C1—C13—C12	45.08 (15)	C10—C11—O1—C12	168.89 (12)
N1—C1—C13—C14	39.14 (14)	C13—C12—O1—C11	42.84 (16)
C2—C1—C13—C14	162.14 (11)	O3—C24—O2—C25	−1.3 (3)
C24—C13—C14—C16	101.64 (15)	C13—C24—O2—C25	175.64 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···Cg1ⁱ	0.96	2.84	3.788 (2)	169

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₅NO₃
M_r	387.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.9899 (6), 7.6751 (3), 20.5073 (9)
β (°)	96.881 (2)
V (Å³)	2029.83 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa-APEXII area-detector diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.980, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	22975, 4790, 3176
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.156, 1.05
No. of reflections	4790
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···Cg1ⁱ	0.96	2.84	3.788 (2)	169

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

SN thanks Dr. Babu Vargheese, SAIF, IIT Madras, India, for his help with the data collection. SN thanks SRM management, India, for their support.

References

Biava, M., Porretta, G. C., Poce, G., Deidda, D., Pompei, R., Tafi, A. & Manetti, F. (2005). Bioorg. Med. Chem. 13, 1221–1230. Web of Science CrossRef PubMed CAS Google Scholar
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Volume 65| Part 8| August 2009| Page o1811

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

Methyl 1-methyl-3-p-tolyl-1,2,3,3a,4,11c-hexa­hydro­benzo[f]chromeno[4,3-b]pyrrole-3a-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 1-methyl-3-p-tolyl-1,2,3,3a,4,11c-hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate