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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 3| March 2010| Pages o611-o612

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

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[Caine, B. (1993). Science, 260, 1814-1816.]); Tidey (1992[Tidey, J. W. (1992). Behav. Pharm. 3, 553-566.]); Carlson (1993[Carlson, J. (1993). Neur. Transm. 94, 11-19.]); Sokoloff et al. (1990[Sokoloff, P., Giros, B., Martres, M. P., Bouthenet, M. L. & Schwartz, J. C. (1990). Nature (London), 347, 147-151.]); Wilner (1985[Wilner, P. (1985). Clinical Neuropharm. 18, Suppl. 1, 549-556.]); Sobral & Rocha Gonsalves (2001a[Sobral, A. J. F. N. & Rocha Gonsalves, A. M. D. A. (2001a). J. Porphyrins Phthalocyanines, 5, 428-430.],b[Sobral, A. J. F. N. & Rocha Gonsalves, A. M. D. A. (2001b). J. Porphyrins Phthalocyanines, 5, 861-866.]); Brockmann & Tour (1995[Brockmann, T. W. & Tour, J. M. (1995). J. Am. Chem. Soc. 117, 4437-4447.]); Suslick et al. (1992[Suslick, K. S., Chen, C. T., Meredith, G. R. & Cheng, L. T. (1992). J. Am. Chem. Soc. 114, 6928-6930.]); Di Natale et al. (1998[Di Natale, C., Paolesse, R., Macagnano, A., Mantini, A., Goletti, C., Tarizzo, E. & Amico, A. (1998). Sens. Actuators B, 50, 162-168.]). For related structures, see: Nirmala et al. (2009a[Nirmala, S., Kamala, E. T. S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009a). Acta Cryst. E65, o1811.],b[Nirmala, S., Kamala, E. T. S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009b). Acta Cryst. E65, o2028-o2029.]); Gunasekaran et al. (2009[Gunasekaran, B., Kathiravan, S., Raghunathan, R., Renuga, V. & Manivannan, V. (2009). Acta Cryst. E65, o1033.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For asymmetry parameters, see: Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C24H22ClNO3

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.954, Tmax = 0.957

  • 18246 measured reflections

  • 4759 independent reflections

  • 3643 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 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

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 DA 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[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


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) ΔCs (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.

Refinement top

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.

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
[Figure 1] 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
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 top
Bruker Kappa APEXII
diffractometer
4759 independent reflections
Radiation source: fine-focus sealed tube3643 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 0 pixels mm-1θmax = 28.3°, θmin = 1.7°
ω and ϕ scansh = 1616
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2526
Tmin = 0.954, Tmax = 0.957l = 1010
18246 measured reflections
Refinement top
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 = 1.05 w = 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
Crystal data top
C24H22ClNO3V = 1956.6 (2) Å3
Mr = 407.88Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.6951 (8) ŵ = 0.22 mm1
b = 19.8829 (13) ÅT = 295 K
c = 8.0799 (6) Å0.20 × 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)
Tmin = 0.954, Tmax = 0.957Rint = 0.039
18246 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.05Δρmax = 0.26 e Å3
4759 reflectionsΔρmin = 0.31 e Å3
264 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.41608 (12)0.03370 (9)0.79567 (19)0.0390 (3)
H10.39110.07400.85130.047*
C20.51822 (13)0.01074 (10)0.7918 (2)0.0475 (4)
H20.56180.03590.84390.057*
C30.55817 (14)0.04982 (11)0.7110 (2)0.0528 (5)
H30.62700.06550.71180.063*
C40.49560 (14)0.08579 (10)0.6309 (2)0.0493 (4)
H40.52280.12580.57570.059*
C50.39005 (13)0.06350 (8)0.63013 (18)0.0383 (3)
C60.32741 (14)0.09955 (8)0.5409 (2)0.0441 (4)
H60.35440.13970.48640.053*
C70.22864 (14)0.07645 (8)0.5336 (2)0.0431 (4)
H70.18890.10010.47210.052*
C80.18609 (12)0.01636 (7)0.61941 (19)0.0350 (3)
C90.24015 (11)0.01983 (7)0.71585 (17)0.0309 (3)
C100.34747 (11)0.00277 (7)0.71656 (17)0.0326 (3)
C110.18799 (11)0.08273 (7)0.80899 (17)0.0304 (3)
H110.24440.11690.80380.036*
C120.09886 (11)0.11107 (7)0.73256 (18)0.0313 (3)
C130.02720 (12)0.05300 (7)0.7070 (2)0.0359 (3)
H13A0.02990.07020.66000.043*
H13B0.00810.03270.81800.043*
C140.05563 (13)0.13099 (9)1.0426 (2)0.0445 (4)
H14A0.01270.11921.12730.053*
H14B0.09350.16411.09290.053*
C150.03273 (12)0.15937 (7)0.87920 (19)0.0355 (3)
H150.06840.20350.85770.043*
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*
C220.14094 (12)0.15066 (8)0.56664 (19)0.0365 (3)
C230.28508 (17)0.21789 (11)0.3981 (3)0.0661 (6)
H23A0.26160.26360.42380.099*
H23B0.36380.21590.36640.099*
H23C0.25950.20170.30430.099*
C240.18914 (13)0.05770 (8)1.10856 (19)0.0406 (3)
H24A0.14120.05251.22320.061*
H24B0.23070.01721.07450.061*
H24C0.23830.09461.10630.061*
N10.12435 (10)0.07114 (6)0.99011 (15)0.0346 (3)
O10.08863 (9)0.00275 (6)0.59363 (15)0.0432 (3)
O20.08968 (11)0.16075 (8)0.46603 (17)0.0627 (4)
O30.24040 (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) top
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, º) top
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—C41.7 (3)C22—C12—C15—C1684.34 (15)
C2—C3—C4—C50.9 (3)C13—C12—C15—C1637.50 (17)
C3—C4—C5—C6177.35 (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—C1491.33 (14)
C10—C5—C6—C71.4 (2)C11—C12—C15—C1423.91 (14)
C5—C6—C7—C81.5 (3)C14—C15—C16—C21144.79 (15)
C6—C7—C8—O1176.79 (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—C1785.78 (17)
C7—C8—C9—C104.7 (2)C21—C16—C17—C180.3 (2)
O1—C8—C9—C113.6 (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—C200.5 (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—C11.9 (2)Cl1—C19—C20—C21178.75 (14)
C6—C5—C10—C91.8 (2)C19—C20—C21—C160.9 (3)
C4—C5—C10—C9179.94 (14)C17—C16—C21—C200.7 (3)
C8—C9—C10—C1173.33 (13)C15—C16—C21—C20178.69 (16)
C11—C9—C10—C13.7 (2)C13—C12—C22—O236.0 (2)
C8—C9—C10—C54.7 (2)C11—C12—C22—O2159.04 (15)
C11—C9—C10—C5178.21 (13)C15—C12—C22—O286.05 (18)
C8—C9—C11—N194.21 (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—O390.57 (15)
C10—C9—C11—C12157.18 (13)C15—C14—N1—C24154.95 (13)
N1—C11—C12—C22159.78 (11)C15—C14—N1—C1128.92 (15)
C9—C11—C12—C2278.63 (15)C9—C11—N1—C2472.57 (15)
N1—C11—C12—C1375.95 (13)C12—C11—N1—C24167.29 (12)
C9—C11—C12—C1345.64 (15)C9—C11—N1—C14164.04 (11)
N1—C11—C12—C1541.11 (13)C12—C11—N1—C1443.90 (13)
C9—C11—C12—C15162.70 (11)C9—C8—O1—C1316.3 (2)
C22—C12—C13—O167.74 (15)C7—C8—O1—C13165.30 (14)
C11—C12—C13—O159.45 (15)C12—C13—O1—C845.08 (18)
C15—C12—C13—O1171.13 (11)O2—C22—O3—C230.4 (3)
N1—C14—C15—C16125.40 (13)C12—C22—O3—C23177.05 (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···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, z1/2.

Experimental details

Crystal data
Chemical formulaC24H22ClNO3
Mr407.88
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)12.6951 (8), 19.8829 (13), 8.0799 (6)
β (°) 106.396 (4)
V3)1956.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.954, 0.957
No. of measured, independent and
observed [I > 2σ(I)] reflections
18246, 4759, 3643
Rint0.039
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.119, 1.05
No. of reflections4759
No. of parameters264
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···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, z1/2.
 

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
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