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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): o611–o612.
Published online 2010 February 13. doi:  10.1107/S1600536810005465
PMCID: PMC2983657

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

Abstract

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 [triangle]); Tidey (1992 [triangle]); Carlson (1993 [triangle]); Sokoloff et al. (1990 [triangle]); Wilner (1985 [triangle]); Sobral & Rocha Gonsalves (2001a [triangle],b [triangle]); Brockmann & Tour (1995 [triangle]); Suslick et al. (1992 [triangle]); Di Natale et al. (1998 [triangle]). For related structures, see: Nirmala et al. (2009a [triangle],b [triangle]); Gunasekaran et al. (2009 [triangle]). For puckering parameters, see: Cremer & Pople (1975 [triangle]). For asymmetry parameters, see: Nardelli (1983 [triangle]).

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Object name is e-66-0o611-scheme1.jpg

Experimental

Crystal data

  • C24H22ClNO3
  • M r = 407.88
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o611-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.119
  • S = 1.05
  • 4759 reflections
  • 264 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.31 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005465/is2523Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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) ΔCs (C11) = 4.05 (3) and with the puckering parameters (Cremer & Pople, 1975) q2 = 0.4275 (2) Å and [var phi]2 = 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 [var phi] = 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.

Experimental

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.

Refinement

H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C24H22ClNO3F(000) = 856
Mr = 407.88Dx = 1.385 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7245 reflections
a = 12.6951 (8) Åθ = 2.6–28.0°
b = 19.8829 (13) ŵ = 0.22 mm1
c = 8.0799 (6) ÅT = 295 K
β = 106.396 (4)°Block, colourless
V = 1956.6 (2) Å30.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer4759 independent reflections
Radiation source: fine-focus sealed tube3643 reflections with I > 2σ(I)
graphiteRint = 0.039
Detector resolution: 0 pixels mm-1θmax = 28.3°, θmin = 1.7°
ω and [var phi] scansh = −16→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −25→26
Tmin = 0.954, Tmax = 0.957l = −10→10
18246 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0498P)2 + 0.5781P] where P = (Fo2 + 2Fc2)/3
4759 reflections(Δ/σ)max = 0.012
264 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.31 e Å3

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

xyzUiso*/Ueq
C1−0.41608 (12)0.03370 (9)0.79567 (19)0.0390 (3)
H1−0.39110.07400.85130.047*
C2−0.51822 (13)0.01074 (10)0.7918 (2)0.0475 (4)
H2−0.56180.03590.84390.057*
C3−0.55817 (14)−0.04982 (11)0.7110 (2)0.0528 (5)
H3−0.6270−0.06550.71180.063*
C4−0.49560 (14)−0.08579 (10)0.6309 (2)0.0493 (4)
H4−0.5228−0.12580.57570.059*
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)
H6−0.3544−0.13970.48640.053*
C7−0.22864 (14)−0.07645 (8)0.5336 (2)0.0431 (4)
H7−0.1889−0.10010.47210.052*
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)
H11−0.24440.11690.80380.036*
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)
H13A0.02990.07020.66000.043*
H13B0.00810.03270.81800.043*
C14−0.05563 (13)0.13099 (9)1.0426 (2)0.0445 (4)
H14A0.01270.11921.12730.053*
H14B−0.09350.16411.09290.053*
C15−0.03273 (12)0.15937 (7)0.87920 (19)0.0355 (3)
H15−0.06840.20350.85770.043*
C160.08658 (11)0.16971 (7)0.88440 (18)0.0328 (3)
C170.17038 (12)0.12687 (7)0.97076 (19)0.0359 (3)
H170.15390.09021.03030.043*
C180.27803 (13)0.13754 (8)0.97024 (19)0.0393 (3)
H180.33330.10831.02840.047*
C190.30196 (13)0.19206 (8)0.8823 (2)0.0420 (4)
C200.22150 (15)0.23519 (9)0.7951 (2)0.0526 (4)
H200.23850.27150.73480.063*
C210.11452 (14)0.22398 (8)0.7978 (2)0.0479 (4)
H210.05990.25370.74000.057*
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−0.26160.26360.42380.099*
H23B−0.36380.21590.36640.099*
H23C−0.25950.20170.30430.099*
C24−0.18914 (13)0.05770 (8)1.10856 (19)0.0406 (3)
H24A−0.14120.05251.22320.061*
H24B−0.23070.01721.07450.061*
H24C−0.23830.09461.10630.061*
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)
Cl10.43761 (4)0.20640 (3)0.88362 (8)0.07301 (19)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0372 (8)0.0499 (9)0.0318 (7)0.0016 (7)0.0126 (6)0.0035 (6)
C20.0370 (8)0.0716 (12)0.0374 (8)0.0018 (8)0.0162 (6)0.0084 (8)
C30.0387 (9)0.0759 (13)0.0453 (9)−0.0137 (9)0.0146 (7)0.0119 (9)
C40.0474 (9)0.0571 (11)0.0416 (9)−0.0176 (8)0.0096 (7)0.0057 (8)
C50.0408 (8)0.0416 (8)0.0315 (7)−0.0065 (6)0.0086 (6)0.0050 (6)
C60.0538 (10)0.0364 (8)0.0421 (8)−0.0101 (7)0.0134 (7)−0.0065 (7)
C70.0510 (9)0.0381 (8)0.0441 (9)−0.0018 (7)0.0197 (7)−0.0099 (7)
C80.0371 (7)0.0349 (7)0.0361 (7)−0.0015 (6)0.0154 (6)−0.0034 (6)
C90.0344 (7)0.0309 (7)0.0293 (6)0.0001 (6)0.0122 (5)0.0004 (5)
C100.0345 (7)0.0372 (7)0.0269 (6)−0.0009 (6)0.0101 (5)0.0050 (5)
C110.0327 (7)0.0298 (7)0.0320 (7)0.0022 (5)0.0147 (5)−0.0022 (5)
C120.0302 (7)0.0318 (7)0.0342 (7)−0.0005 (5)0.0130 (5)−0.0039 (6)
C130.0335 (7)0.0369 (8)0.0412 (8)−0.0008 (6)0.0169 (6)−0.0086 (6)
C140.0430 (8)0.0553 (10)0.0380 (8)−0.0093 (7)0.0161 (7)−0.0149 (7)
C150.0347 (7)0.0332 (7)0.0392 (8)−0.0005 (6)0.0112 (6)−0.0075 (6)
C160.0350 (7)0.0282 (7)0.0348 (7)−0.0031 (5)0.0091 (6)−0.0028 (5)
C170.0419 (8)0.0316 (7)0.0350 (7)−0.0006 (6)0.0123 (6)0.0041 (6)
C180.0374 (8)0.0406 (8)0.0390 (8)0.0028 (6)0.0094 (6)0.0001 (6)
C190.0357 (8)0.0456 (9)0.0457 (9)−0.0091 (7)0.0129 (6)−0.0045 (7)
C200.0534 (10)0.0429 (9)0.0603 (11)−0.0119 (8)0.0139 (8)0.0153 (8)
C210.0426 (9)0.0363 (8)0.0586 (10)−0.0013 (7)0.0042 (7)0.0133 (7)
C220.0373 (8)0.0358 (7)0.0378 (7)−0.0062 (6)0.0129 (6)−0.0039 (6)
C230.0531 (11)0.0644 (13)0.0772 (14)0.0042 (9)0.0127 (10)0.0339 (11)
C240.0484 (9)0.0450 (9)0.0325 (7)0.0021 (7)0.0180 (6)−0.0012 (6)
N10.0367 (6)0.0390 (7)0.0302 (6)0.0013 (5)0.0127 (5)−0.0045 (5)
O10.0407 (6)0.0439 (6)0.0530 (6)−0.0066 (5)0.0262 (5)−0.0194 (5)
O20.0641 (8)0.0837 (10)0.0493 (7)0.0096 (7)0.0309 (6)0.0169 (7)
O30.0418 (6)0.0609 (8)0.0655 (8)0.0096 (6)0.0203 (6)0.0279 (6)
Cl10.0447 (3)0.0830 (4)0.0973 (4)−0.0185 (2)0.0299 (3)−0.0060 (3)

Geometric parameters (Å, °)

C1—C21.367 (2)C14—N11.466 (2)
C1—C101.417 (2)C14—C151.537 (2)
C1—H10.9300C14—H14A0.9700
C2—C31.395 (3)C14—H14B0.9700
C2—H20.9300C15—C161.5174 (19)
C3—C41.360 (3)C15—H150.9800
C3—H30.9300C16—C211.386 (2)
C4—C51.413 (2)C16—C171.387 (2)
C4—H40.9300C17—C181.384 (2)
C5—C61.410 (2)C17—H170.9300
C5—C101.423 (2)C18—C191.376 (2)
C6—C71.352 (2)C18—H180.9300
C6—H60.9300C19—C201.367 (2)
C7—C81.410 (2)C19—Cl11.7425 (16)
C7—H70.9300C20—C211.383 (2)
C8—O11.3653 (17)C20—H200.9300
C8—C91.3776 (19)C21—H210.9300
C9—C101.4361 (19)C22—O21.1930 (18)
C9—C111.5126 (19)C22—O31.3325 (19)
C11—N11.4765 (18)C23—O31.444 (2)
C11—C121.5406 (18)C23—H23A0.9600
C11—H110.9800C23—H23B0.9600
C12—C221.516 (2)C23—H23C0.9600
C12—C131.5198 (19)C24—N11.4520 (18)
C12—C151.5714 (19)C24—H24A0.9600
C13—O11.4289 (18)C24—H24B0.9600
C13—H13A0.9700C24—H24C0.9600
C13—H13B0.9700
C2—C1—C10121.25 (16)N1—C14—H14A110.3
C2—C1—H1119.4C15—C14—H14A110.3
C10—C1—H1119.4N1—C14—H14B110.3
C1—C2—C3121.08 (16)C15—C14—H14B110.3
C1—C2—H2119.5H14A—C14—H14B108.6
C3—C2—H2119.5C16—C15—C14117.09 (13)
C4—C3—C2119.50 (15)C16—C15—C12114.85 (11)
C4—C3—H3120.3C14—C15—C12103.47 (12)
C2—C3—H3120.3C16—C15—H15106.9
C3—C4—C5121.27 (17)C14—C15—H15106.9
C3—C4—H4119.4C12—C15—H15106.9
C5—C4—H4119.4C21—C16—C17117.57 (14)
C6—C5—C4121.01 (15)C21—C16—C15119.16 (13)
C6—C5—C10119.41 (14)C17—C16—C15123.26 (13)
C4—C5—C10119.55 (15)C18—C17—C16121.46 (14)
C7—C6—C5120.90 (15)C18—C17—H17119.3
C7—C6—H6119.6C16—C17—H17119.3
C5—C6—H6119.6C19—C18—C17118.97 (14)
C6—C7—C8119.81 (15)C19—C18—H18120.5
C6—C7—H7120.1C17—C18—H18120.5
C8—C7—H7120.1C20—C19—C18121.23 (15)
O1—C8—C9123.95 (13)C20—C19—Cl1119.60 (13)
O1—C8—C7113.48 (12)C18—C19—Cl1119.17 (13)
C9—C8—C7122.55 (14)C19—C20—C21119.02 (15)
C8—C9—C10117.61 (13)C19—C20—H20120.5
C8—C9—C11119.69 (12)C21—C20—H20120.5
C10—C9—C11122.64 (12)C20—C21—C16121.75 (15)
C1—C10—C5117.32 (13)C20—C21—H21119.1
C1—C10—C9123.12 (14)C16—C21—H21119.1
C5—C10—C9119.54 (13)O2—C22—O3122.82 (15)
N1—C11—C9113.84 (11)O2—C22—C12124.48 (14)
N1—C11—C12101.31 (11)O3—C22—C12112.61 (12)
C9—C11—C12111.78 (11)O3—C23—H23A109.5
N1—C11—H11109.9O3—C23—H23B109.5
C9—C11—H11109.9H23A—C23—H23B109.5
C12—C11—H11109.9O3—C23—H23C109.5
C22—C12—C13110.44 (12)H23A—C23—H23C109.5
C22—C12—C11115.41 (11)H23B—C23—H23C109.5
C13—C12—C11108.19 (12)N1—C24—H24A109.5
C22—C12—C15109.24 (12)N1—C24—H24B109.5
C13—C12—C15110.73 (11)H24A—C24—H24B109.5
C11—C12—C15102.58 (10)N1—C24—H24C109.5
O1—C13—C12112.27 (12)H24A—C24—H24C109.5
O1—C13—H13A109.1H24B—C24—H24C109.5
C12—C13—H13A109.1C24—N1—C14111.13 (12)
O1—C13—H13B109.1C24—N1—C11115.39 (12)
C12—C13—H13B109.1C14—N1—C11105.92 (12)
H13A—C13—H13B107.9C8—O1—C13116.81 (11)
N1—C14—C15106.93 (12)C22—O3—C23116.61 (14)
C10—C1—C2—C30.6 (2)N1—C14—C15—C122.04 (15)
C1—C2—C3—C4−1.7 (3)C22—C12—C15—C16−84.34 (15)
C2—C3—C4—C50.9 (3)C13—C12—C15—C1637.50 (17)
C3—C4—C5—C6−177.35 (16)C11—C12—C15—C16152.74 (12)
C3—C4—C5—C100.9 (2)C22—C12—C15—C14146.84 (12)
C4—C5—C6—C7176.87 (16)C13—C12—C15—C14−91.33 (14)
C10—C5—C6—C7−1.4 (2)C11—C12—C15—C1423.91 (14)
C5—C6—C7—C81.5 (3)C14—C15—C16—C21−144.79 (15)
C6—C7—C8—O1−176.79 (15)C12—C15—C16—C2193.52 (17)
C6—C7—C8—C91.7 (3)C14—C15—C16—C1735.9 (2)
O1—C8—C9—C10173.56 (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—C18179.04 (13)
C7—C8—C9—C11178.12 (14)C16—C17—C18—C190.2 (2)
C2—C1—C10—C51.2 (2)C17—C18—C19—C20−0.5 (2)
C2—C1—C10—C9179.29 (14)C17—C18—C19—Cl1179.12 (12)
C6—C5—C10—C1176.35 (14)C18—C19—C20—C210.8 (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—C9179.94 (14)C17—C16—C21—C200.7 (3)
C8—C9—C10—C1−173.33 (13)C15—C16—C21—C20−178.69 (16)
C11—C9—C10—C13.7 (2)C13—C12—C22—O2−36.0 (2)
C8—C9—C10—C54.7 (2)C11—C12—C22—O2−159.04 (15)
C11—C9—C10—C5−178.21 (13)C15—C12—C22—O286.05 (18)
C8—C9—C11—N1−94.21 (15)C13—C12—C22—O3147.42 (13)
C10—C9—C11—N188.77 (16)C11—C12—C22—O324.34 (18)
C8—C9—C11—C1219.84 (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—C2278.63 (15)C9—C11—N1—C24−72.57 (15)
N1—C11—C12—C1375.95 (13)C12—C11—N1—C24167.29 (12)
C9—C11—C12—C13−45.64 (15)C9—C11—N1—C14164.04 (11)
N1—C11—C12—C15−41.11 (13)C12—C11—N1—C1443.90 (13)
C9—C11—C12—C15−162.70 (11)C9—C8—O1—C1316.3 (2)
C22—C12—C13—O1−67.74 (15)C7—C8—O1—C13−165.30 (14)
C11—C12—C13—O159.45 (15)C12—C13—O1—C8−45.08 (18)
C15—C12—C13—O1171.13 (11)O2—C22—O3—C230.4 (3)
N1—C14—C15—C16−125.40 (13)C12—C22—O3—C23177.05 (15)

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···AD—HH···AD···AD—H···A
C17—H17···Cg2i0.932.993.615 (6)126
C18—H18···Cg1i0.932.753.637 (5)159
C20—H20···Cg3ii0.932.893.651 (9)139

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2523).

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