Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9b-hexa­hydro­benzo[f]chromeno[4,3-b]pyrrole-3a-carboxyl­ate

Gunasekaran, B.; Kathiravan, S.; Raghunathan, R.; Renuga, V.; Manivannan, V.

doi:10.1107/S1600536809012914

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1033

doi:10.1107/S1600536809012914

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Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9b-hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate

B. Gunasekaran,^a S. Kathiravan,^b R. Raghunathan,^b V. Renuga ^c and V. Manivannan ^d ^*

^aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^cDepartment of Chemistry, National College, Thiruchirapalli, Tamil Nadu, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 30 March 2009; accepted 5 April 2009; online 10 April 2009)

In the title compound, C₂₄H₂₃NO₃, the dihedral angle between the naphthalene ring system and the phenyl ring is 76.82 (6)°. The pyrrolidine ring adopts an envelope conformation. In the crystal, weak intermolecular C—H⋯O and C—H⋯π interactions are observed.

Related literature

For the biological activity of chromenopyrrole, see: Caine (1993 ); Tidey (1992 ); Carlson (1993 ); Sokoloff et al. (1990 ); Wilner (1985 ); Sobral & Rocha Gonsalves (2001a ,b ); Brockmann & Tour (1995 ); Suslick et al. (1992 ); Di Natale et al. (1998 ). For a related structure, see: Nirmala et al. (2008 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₄H₂₃NO₃
M_r = 373.43
Monoclinic, P 2₁ /n
a = 13.2332 (6) Å
b = 10.3574 (4) Å
c = 15.0865 (6) Å
β = 111.530 (2)°
V = 1923.50 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEX2 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.979, T_max = 0.987
19089 measured reflections
3499 independent reflections
2413 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.02
3499 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O2ⁱ	0.98	2.53	3.347 (2)	141
C16—H16C⋯Cgⁱⁱ	0.96	2.79	3.689 (4)	156
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1. Cg is the centroid of the C4–C9 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: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012914/is2404sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012914/is2404Isup2.hkl

checkCIF report

Comment top

Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993), aggressiveness (Tidey, 1992), parkinson's disease (Carlson, 1993), psychoses, memory disorders (Sokoloff et al., 1990), anxiety and depression (Wilner, 1985). Pyrroles are also very useful precursors in porphyrin synthesis (Sobral & Rocha Gonsalves, 2001a,b), and as monomers for polymer chemistry (Brockmann & Tour, 1995), with applications ranging from nonlinear optical materials (Suslick et al., 1992) to electronic noses (Di Natale et al., 1998).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Nirmala et al., 2008). The six-membered heterocyclic ring [C7/O1/C11/C12/C13/C8] of the benzochromenopyrrole moiety adopts a half-chair conformation [O1—C7—C8—C13 = 0.5 (2)° and O1—C11—C12—C13 = -60.09 (17)°]. The sum of bond angles around N1 [332.37 (14)°] indicates the sp³ hybridized state of atom N1 in the molecule. The C16—N1—C13—C12 torsion angle is -173.40 (14)°, which corresponds to an antiperiplanar conformation.

The crystal packing is stabilized by weak intramolecular C—H···O and C—H···N interactions. In addition, the structure is stabilized by weak intermolecular C—H···O and C—H···π (C16—H16C···Cg; Cg is the centroid of ring defined by the atoms C4–C9) interactions (Table 1). The C11—H11A···N1 and C13—H13···O3 interactions each generate an S(5) graph set motif (Bernstein et al., 1995).

Related literature top

For the biological activity of chromenopyrrole, see: Caine (1993); Tidey (1992); Carlson (1993); Sokoloff et al. (1990); Wilner (1985); Sobral & Rocha Gonsalves (2001a,b); Brockmann & Tour (1995); Suslick et al. (1992); Di Natale et al. (1998). For a related structure, see: Nirmala et al. (2008). For graph-set notation, see: Bernstein et al. (1995). Cg is the centroid of the C4–C9 ring.

Experimental top

A mixture of (z)-methyl-5-(1-formylnathalen-2-yl-)-3-phenylpent -2-enoate and sarcosine were 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.

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), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.

Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9b- hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate top

Crystal data top

C₂₄H₂₃NO₃	F(000) = 792
M_r = 373.43	D_x = 1.290 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3865 reflections
a = 13.2332 (6) Å	θ = 1.8–25.3°
b = 10.3574 (4) Å	µ = 0.09 mm⁻¹
c = 15.0865 (6) Å	T = 293 K
β = 111.530 (2)°	Block, colourless
V = 1923.50 (14) Å³	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker Kappa APEX2 CCD diffractometer	3499 independent reflections
Radiation source: fine-focus sealed tube	2413 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 0 pixels mm^-1	θ_max = 25.3°, θ_min = 2.4°
ω and ϕ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→12
T_min = 0.979, T_max = 0.987	l = −18→18
19089 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0458P)² + 0.3587P] where P = (F_o² + 2F_c²)/3
3499 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₄H₂₃NO₃	V = 1923.50 (14) Å³
M_r = 373.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.2332 (6) Å	µ = 0.09 mm⁻¹
b = 10.3574 (4) Å	T = 293 K
c = 15.0865 (6) Å	0.25 × 0.20 × 0.15 mm
β = 111.530 (2)°

Data collection top

Bruker Kappa APEX2 CCD diffractometer	3499 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2413 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.987	R_int = 0.041
19089 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.02	Δρ_max = 0.14 e Å⁻³
3499 reflections	Δρ_min = −0.14 e Å⁻³
255 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
O1	0.87620 (10)	0.79656 (11)	0.16896 (8)	0.0560 (3)
O3	0.64358 (10)	1.04425 (13)	0.12731 (9)	0.0610 (4)
C8	0.80155 (13)	0.91239 (15)	0.02018 (11)	0.0404 (4)
O2	0.72839 (11)	0.94550 (14)	0.26458 (9)	0.0684 (4)
C7	0.83173 (14)	0.80090 (16)	0.07191 (12)	0.0473 (4)
N1	0.91939 (11)	1.10692 (13)	0.08087 (9)	0.0452 (4)
C13	0.81799 (13)	1.03987 (15)	0.07102 (10)	0.0388 (4)
H13	0.7558	1.0965	0.0393	0.047*
C9	0.74815 (13)	0.90220 (16)	−0.08105 (12)	0.0452 (4)
C11	0.91380 (14)	0.91616 (15)	0.21733 (12)	0.0483 (4)
H11A	0.9827	0.9387	0.2124	0.058*
H11B	0.9258	0.9059	0.2843	0.058*
C10	0.70597 (14)	1.00976 (19)	−0.14052 (12)	0.0508 (4)
H10	0.7133	1.0915	−0.1134	0.061*
C4	0.73409 (15)	0.77937 (18)	−0.12524 (13)	0.0553 (5)
C12	0.83340 (13)	1.02418 (15)	0.17618 (10)	0.0394 (4)
C23	0.73092 (14)	0.99806 (16)	0.19506 (11)	0.0439 (4)
C6	0.81600 (17)	0.67864 (17)	0.02815 (15)	0.0605 (5)
H6	0.8373	0.6044	0.0650	0.073*
C17	0.95781 (14)	1.15779 (15)	0.32102 (11)	0.0440 (4)
C15	0.88052 (14)	1.15911 (15)	0.21892 (11)	0.0448 (4)
H15	0.8187	1.2134	0.2160	0.054*
C5	0.76969 (17)	0.66982 (19)	−0.06782 (15)	0.0665 (6)
H5	0.7613	0.5889	−0.0964	0.080*
C16	0.93000 (15)	1.15213 (18)	−0.00619 (12)	0.0555 (5)
H16A	0.8733	1.2130	−0.0371	0.083*
H16B	0.9244	1.0802	−0.0479	0.083*
H16C	0.9993	1.1931	0.0087	0.083*
C3	0.68054 (18)	0.7705 (2)	−0.22541 (15)	0.0715 (6)
H3	0.6717	0.6900	−0.2546	0.086*
C22	1.06811 (15)	1.14119 (17)	0.34720 (13)	0.0580 (5)
H22	1.0977	1.1295	0.3006	0.070*
C1	0.65478 (16)	0.9971 (2)	−0.23651 (13)	0.0629 (5)
H1	0.6280	1.0699	−0.2738	0.076*
C2	0.64222 (18)	0.8763 (3)	−0.27927 (15)	0.0753 (6)
H2	0.6075	0.8685	−0.3449	0.090*
C14	0.92485 (17)	1.21276 (17)	0.14582 (12)	0.0580 (5)
H14A	0.8811	1.2850	0.1117	0.070*
H14B	0.9992	1.2417	0.1771	0.070*
C18	0.91714 (17)	1.17418 (17)	0.39259 (12)	0.0571 (5)
H18	0.8428	1.1855	0.3765	0.069*
C19	0.9842 (2)	1.1741 (2)	0.48683 (14)	0.0760 (7)
H19	0.9550	1.1846	0.5338	0.091*
C21	1.13528 (18)	1.14174 (19)	0.44215 (15)	0.0725 (6)
H21	1.2097	1.1306	0.4588	0.087*
C20	1.0936 (2)	1.1585 (2)	0.51178 (15)	0.0784 (7)
H20	1.1392	1.1594	0.5756	0.094*
C24	0.54215 (16)	1.0313 (2)	0.14187 (16)	0.0749 (6)
H24A	0.5298	0.9421	0.1518	0.112*
H24B	0.4839	1.0628	0.0868	0.112*
H24C	0.5453	1.0806	0.1967	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0678 (9)	0.0358 (7)	0.0620 (8)	0.0033 (6)	0.0211 (6)	0.0046 (6)
O3	0.0449 (7)	0.0785 (9)	0.0673 (8)	0.0114 (7)	0.0296 (6)	0.0219 (7)
C8	0.0387 (9)	0.0373 (9)	0.0525 (10)	−0.0033 (7)	0.0254 (8)	−0.0041 (8)
O2	0.0685 (9)	0.0824 (10)	0.0587 (8)	−0.0099 (7)	0.0284 (7)	0.0197 (7)
C7	0.0473 (11)	0.0413 (10)	0.0600 (11)	−0.0024 (8)	0.0278 (9)	−0.0016 (8)
N1	0.0440 (9)	0.0439 (8)	0.0500 (8)	−0.0079 (6)	0.0199 (6)	0.0019 (6)
C13	0.0379 (9)	0.0367 (9)	0.0441 (9)	0.0004 (7)	0.0180 (7)	0.0023 (7)
C9	0.0407 (10)	0.0490 (10)	0.0540 (10)	−0.0075 (8)	0.0270 (8)	−0.0092 (8)
C11	0.0501 (11)	0.0396 (10)	0.0527 (10)	0.0019 (8)	0.0159 (8)	0.0033 (8)
C10	0.0472 (10)	0.0607 (12)	0.0481 (10)	−0.0038 (9)	0.0217 (8)	−0.0073 (9)
C4	0.0563 (12)	0.0537 (12)	0.0659 (12)	−0.0100 (9)	0.0343 (10)	−0.0151 (10)
C12	0.0400 (9)	0.0372 (9)	0.0411 (8)	0.0006 (7)	0.0151 (7)	0.0032 (7)
C23	0.0505 (11)	0.0385 (9)	0.0441 (9)	−0.0032 (8)	0.0190 (8)	−0.0006 (8)
C6	0.0731 (14)	0.0364 (10)	0.0847 (14)	−0.0042 (9)	0.0437 (11)	−0.0044 (9)
C17	0.0488 (11)	0.0331 (9)	0.0479 (9)	−0.0020 (8)	0.0150 (8)	−0.0029 (7)
C15	0.0481 (10)	0.0374 (9)	0.0470 (9)	0.0000 (8)	0.0151 (8)	−0.0005 (7)
C5	0.0817 (15)	0.0477 (12)	0.0858 (15)	−0.0156 (11)	0.0492 (12)	−0.0239 (11)
C16	0.0533 (12)	0.0587 (12)	0.0626 (11)	−0.0069 (9)	0.0310 (9)	0.0072 (9)
C3	0.0717 (15)	0.0794 (16)	0.0716 (14)	−0.0169 (12)	0.0357 (12)	−0.0354 (12)
C22	0.0532 (12)	0.0536 (12)	0.0621 (12)	−0.0017 (9)	0.0151 (9)	−0.0105 (9)
C1	0.0578 (12)	0.0812 (15)	0.0518 (11)	0.0006 (10)	0.0225 (9)	−0.0056 (10)
C2	0.0688 (15)	0.1018 (19)	0.0555 (12)	−0.0036 (13)	0.0228 (11)	−0.0226 (13)
C14	0.0734 (14)	0.0471 (11)	0.0495 (10)	−0.0171 (9)	0.0178 (9)	−0.0005 (8)
C18	0.0661 (13)	0.0527 (11)	0.0553 (11)	−0.0083 (9)	0.0255 (10)	−0.0086 (9)
C19	0.104 (2)	0.0731 (15)	0.0519 (12)	−0.0254 (13)	0.0300 (13)	−0.0113 (10)
C21	0.0602 (14)	0.0545 (13)	0.0789 (15)	−0.0040 (10)	−0.0026 (12)	−0.0073 (11)
C20	0.103 (2)	0.0590 (14)	0.0502 (12)	−0.0214 (13)	0.0010 (13)	−0.0019 (10)
C24	0.0524 (13)	0.0869 (16)	0.1010 (16)	0.0095 (11)	0.0467 (12)	0.0171 (13)

Geometric parameters (Å, º) top

O1—C7	1.3637 (19)	C17—C18	1.382 (2)
O1—C11	1.4311 (19)	C17—C15	1.504 (2)
O3—C23	1.320 (2)	C15—C14	1.531 (2)
O3—C24	1.444 (2)	C15—H15	0.9800
C8—C7	1.369 (2)	C5—H5	0.9300
C8—C9	1.432 (2)	C16—H16A	0.9600
C8—C13	1.502 (2)	C16—H16B	0.9600
O2—C23	1.1931 (18)	C16—H16C	0.9600
C7—C6	1.408 (2)	C3—C2	1.347 (3)
N1—C16	1.449 (2)	C3—H3	0.9300
N1—C14	1.454 (2)	C22—C21	1.381 (3)
N1—C13	1.469 (2)	C22—H22	0.9300
C13—C12	1.532 (2)	C1—C2	1.389 (3)
C13—H13	0.9800	C1—H1	0.9300
C9—C10	1.411 (2)	C2—H2	0.9300
C9—C4	1.417 (2)	C14—H14A	0.9700
C11—C12	1.511 (2)	C14—H14B	0.9700
C11—H11A	0.9700	C18—C19	1.372 (3)
C11—H11B	0.9700	C18—H18	0.9300
C10—C1	1.361 (2)	C19—C20	1.364 (3)
C10—H10	0.9300	C19—H19	0.9300
C4—C5	1.400 (3)	C21—C20	1.365 (3)
C4—C3	1.417 (3)	C21—H21	0.9300
C12—C23	1.509 (2)	C20—H20	0.9300
C12—C15	1.569 (2)	C24—H24A	0.9600
C6—C5	1.352 (3)	C24—H24B	0.9600
C6—H6	0.9300	C24—H24C	0.9600
C17—C22	1.376 (2)

C7—O1—C11	116.82 (12)	C14—C15—C12	103.10 (12)
C23—O3—C24	116.58 (14)	C17—C15—H15	107.1
C7—C8—C9	118.20 (15)	C14—C15—H15	107.1
C7—C8—C13	119.55 (14)	C12—C15—H15	107.1
C9—C8—C13	122.11 (14)	C6—C5—C4	121.67 (17)
O1—C7—C8	124.11 (15)	C6—C5—H5	119.2
O1—C7—C6	113.89 (16)	C4—C5—H5	119.2
C8—C7—C6	121.97 (16)	N1—C16—H16A	109.5
C16—N1—C14	111.70 (13)	N1—C16—H16B	109.5
C16—N1—C13	116.73 (13)	H16A—C16—H16B	109.5
C14—N1—C13	104.01 (13)	N1—C16—H16C	109.5
N1—C13—C8	115.02 (13)	H16A—C16—H16C	109.5
N1—C13—C12	100.13 (12)	H16B—C16—H16C	109.5
C8—C13—C12	112.01 (13)	C2—C3—C4	121.4 (2)
N1—C13—H13	109.8	C2—C3—H3	119.3
C8—C13—H13	109.8	C4—C3—H3	119.3
C12—C13—H13	109.8	C17—C22—C21	120.56 (19)
C10—C9—C4	117.20 (15)	C17—C22—H22	119.7
C10—C9—C8	123.04 (15)	C21—C22—H22	119.7
C4—C9—C8	119.75 (16)	C10—C1—C2	120.6 (2)
O1—C11—C12	111.76 (13)	C10—C1—H1	119.7
O1—C11—H11A	109.3	C2—C1—H1	119.7
C12—C11—H11A	109.3	C3—C2—C1	119.85 (19)
O1—C11—H11B	109.3	C3—C2—H2	120.1
C12—C11—H11B	109.3	C1—C2—H2	120.1
H11A—C11—H11B	107.9	N1—C14—C15	105.93 (13)
C1—C10—C9	121.78 (18)	N1—C14—H14A	110.6
C1—C10—H10	119.1	C15—C14—H14A	110.6
C9—C10—H10	119.1	N1—C14—H14B	110.6
C5—C4—C9	118.71 (17)	C15—C14—H14B	110.6
C5—C4—C3	122.04 (19)	H14A—C14—H14B	108.7
C9—C4—C3	119.19 (19)	C19—C18—C17	121.3 (2)
C23—C12—C11	109.62 (13)	C19—C18—H18	119.3
C23—C12—C13	115.29 (13)	C17—C18—H18	119.3
C11—C12—C13	108.05 (13)	C20—C19—C18	120.2 (2)
C23—C12—C15	109.34 (13)	C20—C19—H19	119.9
C11—C12—C15	112.14 (13)	C18—C19—H19	119.9
C13—C12—C15	102.29 (12)	C20—C21—C22	120.7 (2)
O2—C23—O3	123.16 (16)	C20—C21—H21	119.7
O2—C23—C12	124.39 (16)	C22—C21—H21	119.7
O3—C23—C12	112.40 (13)	C19—C20—C21	119.35 (19)
C5—C6—C7	119.59 (18)	C19—C20—H20	120.3
C5—C6—H6	120.2	C21—C20—H20	120.3
C7—C6—H6	120.2	O3—C24—H24A	109.5
C22—C17—C18	117.86 (16)	O3—C24—H24B	109.5
C22—C17—C15	123.11 (16)	H24A—C24—H24B	109.5
C18—C17—C15	119.03 (16)	O3—C24—H24C	109.5
C17—C15—C14	116.40 (15)	H24A—C24—H24C	109.5
C17—C15—C12	115.53 (13)	H24B—C24—H24C	109.5

C11—O1—C7—C8	−13.5 (2)	C13—C12—C23—O2	155.96 (16)
C11—O1—C7—C6	168.25 (15)	C15—C12—C23—O2	−89.50 (19)
C9—C8—C7—O1	−175.27 (14)	C11—C12—C23—O3	−148.53 (14)
C13—C8—C7—O1	0.5 (2)	C13—C12—C23—O3	−26.37 (19)
C9—C8—C7—C6	2.8 (2)	C15—C12—C23—O3	88.17 (16)
C13—C8—C7—C6	178.56 (16)	O1—C7—C6—C5	178.20 (16)
C16—N1—C13—C8	66.33 (19)	C8—C7—C6—C5	−0.1 (3)
C14—N1—C13—C8	−170.14 (13)	C22—C17—C15—C14	−31.9 (2)
C16—N1—C13—C12	−173.44 (13)	C18—C17—C15—C14	148.01 (16)
C14—N1—C13—C12	−49.91 (15)	C22—C17—C15—C12	89.3 (2)
C7—C8—C13—N1	94.95 (17)	C18—C17—C15—C12	−90.82 (19)
C9—C8—C13—N1	−89.46 (18)	C23—C12—C15—C17	88.85 (17)
C7—C8—C13—C12	−18.5 (2)	C11—C12—C15—C17	−32.95 (19)
C9—C8—C13—C12	157.09 (14)	C13—C12—C15—C17	−148.48 (14)
C7—C8—C9—C10	174.89 (15)	C23—C12—C15—C14	−143.05 (14)
C13—C8—C9—C10	−0.8 (2)	C11—C12—C15—C14	95.15 (16)
C7—C8—C9—C4	−3.9 (2)	C13—C12—C15—C14	−20.38 (16)
C13—C8—C9—C4	−179.52 (14)	C7—C6—C5—C4	−1.7 (3)
C7—O1—C11—C12	44.22 (19)	C9—C4—C5—C6	0.5 (3)
C4—C9—C10—C1	−0.7 (2)	C3—C4—C5—C6	−176.74 (18)
C8—C9—C10—C1	−179.46 (15)	C5—C4—C3—C2	176.87 (19)
C10—C9—C4—C5	−176.58 (16)	C9—C4—C3—C2	−0.4 (3)
C8—C9—C4—C5	2.3 (2)	C18—C17—C22—C21	−0.3 (3)
C10—C9—C4—C3	0.8 (2)	C15—C17—C22—C21	179.54 (17)
C8—C9—C4—C3	179.63 (15)	C9—C10—C1—C2	0.1 (3)
O1—C11—C12—C23	66.29 (17)	C4—C3—C2—C1	−0.1 (3)
O1—C11—C12—C13	−60.09 (17)	C10—C1—C2—C3	0.3 (3)
O1—C11—C12—C15	−172.07 (13)	C16—N1—C14—C15	164.03 (14)
N1—C13—C12—C23	160.94 (13)	C13—N1—C14—C15	37.29 (17)
C8—C13—C12—C23	−76.68 (17)	C17—C15—C14—N1	118.28 (16)
N1—C13—C12—C11	−76.07 (15)	C12—C15—C14—N1	−9.28 (17)
C8—C13—C12—C11	46.31 (17)	C22—C17—C18—C19	0.0 (3)
N1—C13—C12—C15	42.39 (15)	C15—C17—C18—C19	−179.84 (17)
C8—C13—C12—C15	164.78 (13)	C17—C18—C19—C20	0.5 (3)
C24—O3—C23—O2	1.5 (3)	C17—C22—C21—C20	0.1 (3)
C24—O3—C23—C12	−176.18 (15)	C18—C19—C20—C21	−0.7 (3)
C11—C12—C23—O2	33.8 (2)	C22—C21—C20—C19	0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···N1	0.97	2.54	2.874 (2)	100
C13—H13···O3	0.98	2.39	2.7366 (19)	100
C15—H15···O2ⁱ	0.98	2.53	3.347 (2)	141
C16—H16C···Cgⁱⁱ	0.96	2.79	3.689 (4)	156

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₃NO₃
M_r	373.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.2332 (6), 10.3574 (4), 15.0865 (6)
β (°)	111.530 (2)
V (Å³)	1923.50 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker Kappa APEX2 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.979, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	19089, 3499, 2413
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.02
No. of reflections	3499
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···N1	0.97	2.54	2.874 (2)	100
C13—H13···O3	0.98	2.39	2.7366 (19)	100
C15—H15···O2ⁱ	0.98	2.53	3.347 (2)	141
C16—H16C···Cgⁱⁱ	0.96	2.79	3.689 (4)	156

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1.

Acknowledgements

Author thanks AMET University Management, India, for their kind support.

References

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

Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9b-hexa­hydro­benzo[f]chromeno[4,3-b]pyrrole-3a-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9b-hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate