Methyl 3-(4-chloro­phen­yl)-1-methyl-1,2,3,3a,4,11c-hexa­hydro­benzo[f]chromeno[4,3-b]pyrrole-3a-carboxyl­ate

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

doi:10.1107/S1600536810005465

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o611-o612

doi:10.1107/S1600536810005465

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Methyl 3-(4-chlorophenyl)-1-methyl-1,2,3,3a,4,11c-hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate

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

^aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: crystallography2010@gmail.com

(Received 7 February 2010; accepted 9 February 2010; online 13 February 2010)

In the title compound, C₂₄H₂₂ClNO₃, the dihedral angle between the naphthalene ring system and the chlorophenyl ring is 67.44 (4)°. The pyrrolidine and dihydropyran rings exhibit envelope and half chair conformations, respectively. In the crystal structure, weak C—H⋯π interactions are observed.

Related literature

For the biological activity of chromenopyrrole derivatives, 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 related structures, see: Nirmala et al. (2009a ,b ); Gunasekaran et al. (2009 ). For puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Nardelli (1983 ).

Experimental

Crystal data

C₂₄H₂₂ClNO₃
M_r = 407.88
Monoclinic, P 2₁ /c
a = 12.6951 (8) Å
b = 19.8829 (13) Å
c = 8.0799 (6) Å
β = 106.396 (4)°
V = 1956.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 295 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.954, T_max = 0.957
18246 measured reflections
4759 independent reflections
3643 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.05
4759 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C5/C10, C5–C10 and C16–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯Cg2ⁱ	0.93	2.99	3.615 (6)	126
C18—H18⋯Cg1ⁱ	0.93	2.75	3.637 (5)	159
C20—H20⋯Cg3ⁱⁱ	0.93	2.89	3.651 (9)	139
Symmetry codes: (i) -x+2, -y, -z+2; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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

Crystal structure: contains datablock I. DOI: 10.1107/S1600536810005465/is2523sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005465/is2523Isup2.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 non linear 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., 2009a, b; Gunasekaran et al., 2009). The dihedral angle between the naphthalene ring system and the chlorophenyl ring is 67.44 (4)°. The pyrrolidine ring [N1/C14/C15/C12/C11] exhibits an envelope conformation with envelope on C11 with an asymmetry parameter (Nardelli, 1983) ΔC_s (C11) = 4.05 (3) and with the puckering parameters (Cremer & Pople, 1975) q2 = 0.4275 (2) Å and ϕ2 = 214.69 (6)°. The six-membered heterocyclic ring [C8/C9/C11/C12/C13/O1] of the benzochromenopyrrole moiety adopts a half-chair conformation with the puckering parameters Q = 0.4697 (2) Å, Θ = 132.51 (3)° and ϕ = 82.84 (5)°. The sum of bond angles around N1 [332.44 (12)°] indicate the sp³ hybridized state of atom N1 in the molecule.

The crystal packing is stabilized by weak intermolecular C—H···π [C17—H17···Cg2(2-x, -y, 2-z), C18—H18···Cg1(2-x, -y, 2-z) and C20—H20···Cg3(x, 1/2-y, -1/2+z); Table 1] interactions. Cg1, Cg2 and Cg3 are the centroids of the rings C1–C5/C10, C5–C10 and C16–C21, respectively.

Related literature top

For the biological activity of chromenopyrrole derivatives, 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 related structures, see: Nirmala et al. (2009a,b); Gunasekaran et al. (2009). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983).

Experimental top

A mixture of (Z)-methyl 2-((1-formylnaphthalen-2-yloxy) methyl) -3-(4-chloro phenylacrylate (20 mmol) and sarcosine (30 mmol) 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. 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: 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 30% probability displacement ellipsoids for non-H atoms.

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

Crystal data top

C₂₄H₂₂ClNO₃	F(000) = 856
M_r = 407.88	D_x = 1.385 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7245 reflections
a = 12.6951 (8) Å	θ = 2.6–28.0°
b = 19.8829 (13) Å	µ = 0.22 mm⁻¹
c = 8.0799 (6) Å	T = 295 K
β = 106.396 (4)°	Block, colourless
V = 1956.6 (2) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4759 independent reflections
Radiation source: fine-focus sealed tube	3643 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.7°
ω and ϕ scans	h = −16→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −25→26
T_min = 0.954, T_max = 0.957	l = −10→10
18246 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0498P)² + 0.5781P] where P = (F_o² + 2F_c²)/3
4759 reflections	(Δ/σ)_max = 0.012
264 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₄H₂₂ClNO₃	V = 1956.6 (2) Å³
M_r = 407.88	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6951 (8) Å	µ = 0.22 mm⁻¹
b = 19.8829 (13) Å	T = 295 K
c = 8.0799 (6) Å	0.20 × 0.20 × 0.20 mm
β = 106.396 (4)°

Data collection top

Bruker Kappa APEXII diffractometer	4759 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3643 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.957	R_int = 0.039
18246 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.05	Δρ_max = 0.26 e Å⁻³
4759 reflections	Δρ_min = −0.31 e Å⁻³
264 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.41608 (12)	0.03370 (9)	0.79567 (19)	0.0390 (3)
H1	−0.3911	0.0740	0.8513	0.047*
C2	−0.51822 (13)	0.01074 (10)	0.7918 (2)	0.0475 (4)
H2	−0.5618	0.0359	0.8439	0.057*
C3	−0.55817 (14)	−0.04982 (11)	0.7110 (2)	0.0528 (5)
H3	−0.6270	−0.0655	0.7118	0.063*
C4	−0.49560 (14)	−0.08579 (10)	0.6309 (2)	0.0493 (4)
H4	−0.5228	−0.1258	0.5757	0.059*
C5	−0.39005 (13)	−0.06350 (8)	0.63013 (18)	0.0383 (3)
C6	−0.32741 (14)	−0.09955 (8)	0.5409 (2)	0.0441 (4)
H6	−0.3544	−0.1397	0.4864	0.053*
C7	−0.22864 (14)	−0.07645 (8)	0.5336 (2)	0.0431 (4)
H7	−0.1889	−0.1001	0.4721	0.052*
C8	−0.18609 (12)	−0.01636 (7)	0.61941 (19)	0.0350 (3)
C9	−0.24015 (11)	0.01983 (7)	0.71585 (17)	0.0309 (3)
C10	−0.34747 (11)	−0.00277 (7)	0.71656 (17)	0.0326 (3)
C11	−0.18799 (11)	0.08273 (7)	0.80899 (17)	0.0304 (3)
H11	−0.2444	0.1169	0.8038	0.036*
C12	−0.09886 (11)	0.11107 (7)	0.73256 (18)	0.0313 (3)
C13	−0.02720 (12)	0.05300 (7)	0.7070 (2)	0.0359 (3)
H13A	0.0299	0.0702	0.6600	0.043*
H13B	0.0081	0.0327	0.8180	0.043*
C14	−0.05563 (13)	0.13099 (9)	1.0426 (2)	0.0445 (4)
H14A	0.0127	0.1192	1.1273	0.053*
H14B	−0.0935	0.1641	1.0929	0.053*
C15	−0.03273 (12)	0.15937 (7)	0.87920 (19)	0.0355 (3)
H15	−0.0684	0.2035	0.8577	0.043*
C16	0.08658 (11)	0.16971 (7)	0.88440 (18)	0.0328 (3)
C17	0.17038 (12)	0.12687 (7)	0.97076 (19)	0.0359 (3)
H17	0.1539	0.0902	1.0303	0.043*
C18	0.27803 (13)	0.13754 (8)	0.97024 (19)	0.0393 (3)
H18	0.3333	0.1083	1.0284	0.047*
C19	0.30196 (13)	0.19206 (8)	0.8823 (2)	0.0420 (4)
C20	0.22150 (15)	0.23519 (9)	0.7951 (2)	0.0526 (4)
H20	0.2385	0.2715	0.7348	0.063*
C21	0.11452 (14)	0.22398 (8)	0.7978 (2)	0.0479 (4)
H21	0.0599	0.2537	0.7400	0.057*
C22	−0.14094 (12)	0.15066 (8)	0.56664 (19)	0.0365 (3)
C23	−0.28508 (17)	0.21789 (11)	0.3981 (3)	0.0661 (6)
H23A	−0.2616	0.2636	0.4238	0.099*
H23B	−0.3638	0.2159	0.3664	0.099*
H23C	−0.2595	0.2017	0.3043	0.099*
C24	−0.18914 (13)	0.05770 (8)	1.10856 (19)	0.0406 (3)
H24A	−0.1412	0.0525	1.2232	0.061*
H24B	−0.2307	0.0172	1.0745	0.061*
H24C	−0.2383	0.0946	1.1063	0.061*
N1	−0.12435 (10)	0.07114 (6)	0.99011 (15)	0.0346 (3)
O1	−0.08863 (9)	0.00275 (6)	0.59363 (15)	0.0432 (3)
O2	−0.08968 (11)	0.16075 (8)	0.46603 (17)	0.0627 (4)
O3	−0.24040 (10)	0.17653 (7)	0.54843 (17)	0.0550 (3)
Cl1	0.43761 (4)	0.20640 (3)	0.88362 (8)	0.07301 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0372 (8)	0.0499 (9)	0.0318 (7)	0.0016 (7)	0.0126 (6)	0.0035 (6)
C2	0.0370 (8)	0.0716 (12)	0.0374 (8)	0.0018 (8)	0.0162 (6)	0.0084 (8)
C3	0.0387 (9)	0.0759 (13)	0.0453 (9)	−0.0137 (9)	0.0146 (7)	0.0119 (9)
C4	0.0474 (9)	0.0571 (11)	0.0416 (9)	−0.0176 (8)	0.0096 (7)	0.0057 (8)
C5	0.0408 (8)	0.0416 (8)	0.0315 (7)	−0.0065 (6)	0.0086 (6)	0.0050 (6)
C6	0.0538 (10)	0.0364 (8)	0.0421 (8)	−0.0101 (7)	0.0134 (7)	−0.0065 (7)
C7	0.0510 (9)	0.0381 (8)	0.0441 (9)	−0.0018 (7)	0.0197 (7)	−0.0099 (7)
C8	0.0371 (7)	0.0349 (7)	0.0361 (7)	−0.0015 (6)	0.0154 (6)	−0.0034 (6)
C9	0.0344 (7)	0.0309 (7)	0.0293 (6)	0.0001 (6)	0.0122 (5)	0.0004 (5)
C10	0.0345 (7)	0.0372 (7)	0.0269 (6)	−0.0009 (6)	0.0101 (5)	0.0050 (5)
C11	0.0327 (7)	0.0298 (7)	0.0320 (7)	0.0022 (5)	0.0147 (5)	−0.0022 (5)
C12	0.0302 (7)	0.0318 (7)	0.0342 (7)	−0.0005 (5)	0.0130 (5)	−0.0039 (6)
C13	0.0335 (7)	0.0369 (8)	0.0412 (8)	−0.0008 (6)	0.0169 (6)	−0.0086 (6)
C14	0.0430 (8)	0.0553 (10)	0.0380 (8)	−0.0093 (7)	0.0161 (7)	−0.0149 (7)
C15	0.0347 (7)	0.0332 (7)	0.0392 (8)	−0.0005 (6)	0.0112 (6)	−0.0075 (6)
C16	0.0350 (7)	0.0282 (7)	0.0348 (7)	−0.0031 (5)	0.0091 (6)	−0.0028 (5)
C17	0.0419 (8)	0.0316 (7)	0.0350 (7)	−0.0006 (6)	0.0123 (6)	0.0041 (6)
C18	0.0374 (8)	0.0406 (8)	0.0390 (8)	0.0028 (6)	0.0094 (6)	0.0001 (6)
C19	0.0357 (8)	0.0456 (9)	0.0457 (9)	−0.0091 (7)	0.0129 (6)	−0.0045 (7)
C20	0.0534 (10)	0.0429 (9)	0.0603 (11)	−0.0119 (8)	0.0139 (8)	0.0153 (8)
C21	0.0426 (9)	0.0363 (8)	0.0586 (10)	−0.0013 (7)	0.0042 (7)	0.0133 (7)
C22	0.0373 (8)	0.0358 (7)	0.0378 (7)	−0.0062 (6)	0.0129 (6)	−0.0039 (6)
C23	0.0531 (11)	0.0644 (13)	0.0772 (14)	0.0042 (9)	0.0127 (10)	0.0339 (11)
C24	0.0484 (9)	0.0450 (9)	0.0325 (7)	0.0021 (7)	0.0180 (6)	−0.0012 (6)
N1	0.0367 (6)	0.0390 (7)	0.0302 (6)	0.0013 (5)	0.0127 (5)	−0.0045 (5)
O1	0.0407 (6)	0.0439 (6)	0.0530 (6)	−0.0066 (5)	0.0262 (5)	−0.0194 (5)
O2	0.0641 (8)	0.0837 (10)	0.0493 (7)	0.0096 (7)	0.0309 (6)	0.0169 (7)
O3	0.0418 (6)	0.0609 (8)	0.0655 (8)	0.0096 (6)	0.0203 (6)	0.0279 (6)
Cl1	0.0447 (3)	0.0830 (4)	0.0973 (4)	−0.0185 (2)	0.0299 (3)	−0.0060 (3)

Geometric parameters (Å, º) top

C1—C2	1.367 (2)	C14—N1	1.466 (2)
C1—C10	1.417 (2)	C14—C15	1.537 (2)
C1—H1	0.9300	C14—H14A	0.9700
C2—C3	1.395 (3)	C14—H14B	0.9700
C2—H2	0.9300	C15—C16	1.5174 (19)
C3—C4	1.360 (3)	C15—H15	0.9800
C3—H3	0.9300	C16—C21	1.386 (2)
C4—C5	1.413 (2)	C16—C17	1.387 (2)
C4—H4	0.9300	C17—C18	1.384 (2)
C5—C6	1.410 (2)	C17—H17	0.9300
C5—C10	1.423 (2)	C18—C19	1.376 (2)
C6—C7	1.352 (2)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.367 (2)
C7—C8	1.410 (2)	C19—Cl1	1.7425 (16)
C7—H7	0.9300	C20—C21	1.383 (2)
C8—O1	1.3653 (17)	C20—H20	0.9300
C8—C9	1.3776 (19)	C21—H21	0.9300
C9—C10	1.4361 (19)	C22—O2	1.1930 (18)
C9—C11	1.5126 (19)	C22—O3	1.3325 (19)
C11—N1	1.4765 (18)	C23—O3	1.444 (2)
C11—C12	1.5406 (18)	C23—H23A	0.9600
C11—H11	0.9800	C23—H23B	0.9600
C12—C22	1.516 (2)	C23—H23C	0.9600
C12—C13	1.5198 (19)	C24—N1	1.4520 (18)
C12—C15	1.5714 (19)	C24—H24A	0.9600
C13—O1	1.4289 (18)	C24—H24B	0.9600
C13—H13A	0.9700	C24—H24C	0.9600
C13—H13B	0.9700

C2—C1—C10	121.25 (16)	N1—C14—H14A	110.3
C2—C1—H1	119.4	C15—C14—H14A	110.3
C10—C1—H1	119.4	N1—C14—H14B	110.3
C1—C2—C3	121.08 (16)	C15—C14—H14B	110.3
C1—C2—H2	119.5	H14A—C14—H14B	108.6
C3—C2—H2	119.5	C16—C15—C14	117.09 (13)
C4—C3—C2	119.50 (15)	C16—C15—C12	114.85 (11)
C4—C3—H3	120.3	C14—C15—C12	103.47 (12)
C2—C3—H3	120.3	C16—C15—H15	106.9
C3—C4—C5	121.27 (17)	C14—C15—H15	106.9
C3—C4—H4	119.4	C12—C15—H15	106.9
C5—C4—H4	119.4	C21—C16—C17	117.57 (14)
C6—C5—C4	121.01 (15)	C21—C16—C15	119.16 (13)
C6—C5—C10	119.41 (14)	C17—C16—C15	123.26 (13)
C4—C5—C10	119.55 (15)	C18—C17—C16	121.46 (14)
C7—C6—C5	120.90 (15)	C18—C17—H17	119.3
C7—C6—H6	119.6	C16—C17—H17	119.3
C5—C6—H6	119.6	C19—C18—C17	118.97 (14)
C6—C7—C8	119.81 (15)	C19—C18—H18	120.5
C6—C7—H7	120.1	C17—C18—H18	120.5
C8—C7—H7	120.1	C20—C19—C18	121.23 (15)
O1—C8—C9	123.95 (13)	C20—C19—Cl1	119.60 (13)
O1—C8—C7	113.48 (12)	C18—C19—Cl1	119.17 (13)
C9—C8—C7	122.55 (14)	C19—C20—C21	119.02 (15)
C8—C9—C10	117.61 (13)	C19—C20—H20	120.5
C8—C9—C11	119.69 (12)	C21—C20—H20	120.5
C10—C9—C11	122.64 (12)	C20—C21—C16	121.75 (15)
C1—C10—C5	117.32 (13)	C20—C21—H21	119.1
C1—C10—C9	123.12 (14)	C16—C21—H21	119.1
C5—C10—C9	119.54 (13)	O2—C22—O3	122.82 (15)
N1—C11—C9	113.84 (11)	O2—C22—C12	124.48 (14)
N1—C11—C12	101.31 (11)	O3—C22—C12	112.61 (12)
C9—C11—C12	111.78 (11)	O3—C23—H23A	109.5
N1—C11—H11	109.9	O3—C23—H23B	109.5
C9—C11—H11	109.9	H23A—C23—H23B	109.5
C12—C11—H11	109.9	O3—C23—H23C	109.5
C22—C12—C13	110.44 (12)	H23A—C23—H23C	109.5
C22—C12—C11	115.41 (11)	H23B—C23—H23C	109.5
C13—C12—C11	108.19 (12)	N1—C24—H24A	109.5
C22—C12—C15	109.24 (12)	N1—C24—H24B	109.5
C13—C12—C15	110.73 (11)	H24A—C24—H24B	109.5
C11—C12—C15	102.58 (10)	N1—C24—H24C	109.5
O1—C13—C12	112.27 (12)	H24A—C24—H24C	109.5
O1—C13—H13A	109.1	H24B—C24—H24C	109.5
C12—C13—H13A	109.1	C24—N1—C14	111.13 (12)
O1—C13—H13B	109.1	C24—N1—C11	115.39 (12)
C12—C13—H13B	109.1	C14—N1—C11	105.92 (12)
H13A—C13—H13B	107.9	C8—O1—C13	116.81 (11)
N1—C14—C15	106.93 (12)	C22—O3—C23	116.61 (14)

C10—C1—C2—C3	0.6 (2)	N1—C14—C15—C12	2.04 (15)
C1—C2—C3—C4	−1.7 (3)	C22—C12—C15—C16	−84.34 (15)
C2—C3—C4—C5	0.9 (3)	C13—C12—C15—C16	37.50 (17)
C3—C4—C5—C6	−177.35 (16)	C11—C12—C15—C16	152.74 (12)
C3—C4—C5—C10	0.9 (2)	C22—C12—C15—C14	146.84 (12)
C4—C5—C6—C7	176.87 (16)	C13—C12—C15—C14	−91.33 (14)
C10—C5—C6—C7	−1.4 (2)	C11—C12—C15—C14	23.91 (14)
C5—C6—C7—C8	1.5 (3)	C14—C15—C16—C21	−144.79 (15)
C6—C7—C8—O1	−176.79 (15)	C12—C15—C16—C21	93.52 (17)
C6—C7—C8—C9	1.7 (3)	C14—C15—C16—C17	35.9 (2)
O1—C8—C9—C10	173.56 (13)	C12—C15—C16—C17	−85.78 (17)
C7—C8—C9—C10	−4.7 (2)	C21—C16—C17—C18	−0.3 (2)
O1—C8—C9—C11	−3.6 (2)	C15—C16—C17—C18	179.04 (13)
C7—C8—C9—C11	178.12 (14)	C16—C17—C18—C19	0.2 (2)
C2—C1—C10—C5	1.2 (2)	C17—C18—C19—C20	−0.5 (2)
C2—C1—C10—C9	179.29 (14)	C17—C18—C19—Cl1	179.12 (12)
C6—C5—C10—C1	176.35 (14)	C18—C19—C20—C21	0.8 (3)
C4—C5—C10—C1	−1.9 (2)	Cl1—C19—C20—C21	−178.75 (14)
C6—C5—C10—C9	−1.8 (2)	C19—C20—C21—C16	−0.9 (3)
C4—C5—C10—C9	179.94 (14)	C17—C16—C21—C20	0.7 (3)
C8—C9—C10—C1	−173.33 (13)	C15—C16—C21—C20	−178.69 (16)
C11—C9—C10—C1	3.7 (2)	C13—C12—C22—O2	−36.0 (2)
C8—C9—C10—C5	4.7 (2)	C11—C12—C22—O2	−159.04 (15)
C11—C9—C10—C5	−178.21 (13)	C15—C12—C22—O2	86.05 (18)
C8—C9—C11—N1	−94.21 (15)	C13—C12—C22—O3	147.42 (13)
C10—C9—C11—N1	88.77 (16)	C11—C12—C22—O3	24.34 (18)
C8—C9—C11—C12	19.84 (18)	C15—C12—C22—O3	−90.57 (15)
C10—C9—C11—C12	−157.18 (13)	C15—C14—N1—C24	−154.95 (13)
N1—C11—C12—C22	−159.78 (11)	C15—C14—N1—C11	−28.92 (15)
C9—C11—C12—C22	78.63 (15)	C9—C11—N1—C24	−72.57 (15)
N1—C11—C12—C13	75.95 (13)	C12—C11—N1—C24	167.29 (12)
C9—C11—C12—C13	−45.64 (15)	C9—C11—N1—C14	164.04 (11)
N1—C11—C12—C15	−41.11 (13)	C12—C11—N1—C14	43.90 (13)
C9—C11—C12—C15	−162.70 (11)	C9—C8—O1—C13	16.3 (2)
C22—C12—C13—O1	−67.74 (15)	C7—C8—O1—C13	−165.30 (14)
C11—C12—C13—O1	59.45 (15)	C12—C13—O1—C8	−45.08 (18)
C15—C12—C13—O1	171.13 (11)	O2—C22—O3—C23	0.4 (3)
N1—C14—C15—C16	−125.40 (13)	C12—C22—O3—C23	177.05 (15)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C1–C5/C10, C5–C10 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg2ⁱ	0.93	2.99	3.615 (6)	126
C18—H18···Cg1ⁱ	0.93	2.75	3.637 (5)	159
C20—H20···Cg3ⁱⁱ	0.93	2.89	3.651 (9)	139

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂ClNO₃
M_r	407.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	12.6951 (8), 19.8829 (13), 8.0799 (6)
β (°)	106.396 (4)
V (Å³)	1956.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.954, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	18246, 4759, 3643
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.05
No. of reflections	4759
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.31

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

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C1–C5/C10, C5–C10 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg2ⁱ	0.93	2.99	3.615 (6)	126
C18—H18···Cg1ⁱ	0.93	2.75	3.637 (5)	159
C20—H20···Cg3ⁱⁱ	0.93	2.89	3.651 (9)	139

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

Acknowledgements

The authors thank AMET University management, India, for their kind support.

References

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Volume 66| Part 3| March 2010| Pages o611-o612

doi:10.1107/S1600536810005465

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

Methyl 3-(4-chloro­phen­yl)-1-methyl-1,2,3,3a,4,11c-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 3-(4-chlorophenyl)-1-methyl-1,2,3,3a,4,11c-hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate