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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 4| April 2010| Pages o810-o811

Methyl 4-(4-chloro­phen­yl)-1,2,3,3a,4,4a,5,12c-octa­hydro­benzo[f]chromeno[3,4-b]pyrrolizine-4a-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 11 February 2010; accepted 1 March 2010; online 13 March 2010)

There are two mol­ecules in the asymmetric unit of the title compound, C26H24ClNO3. The dihedral angles between the naphthalene ring system and the chloro­phenyl substituent are 58.76 (9) and 51.59 (8)° in the two mol­ecules. In the pyrrolizine ring system, both the pyrrolidine rings adopt envelope conformations and the dihydro­pyran rings adopt half-chair conformations. In the pyrrolizine ring system of one of the mol­ecules, one of the C atoms is disordered over two positions with site occupancies of 0.69 (2) and 0.31 (2). The crystal packing is stabilized by weak intra­molecular C—H⋯O inter­actions and the crystal packing is stabilized by weak C—H⋯π inter­actions.

Related literature

For the biological activity of chromenopyrroles, 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.]). For a related structure, see: Nirmala et al. (2009[Nirmala, S., Kamala, E. T. S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009). Acta Cryst. E65, o1938.]). For general background to the bridging of N—C bonds in pyrrolizine rings, see: Ramesh et al. (2007[Ramesh, P., Murugavel, S., SubbiahPandi, A., Murugan, R. & Narayanan, S. S. (2007). Acta Cryst. E63, o4106-o4107.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24ClNO3

  • Mr = 433.91

  • Monoclinic, P 21 /c

  • a = 22.3214 (9) Å

  • b = 10.8122 (5) Å

  • c = 18.5008 (8) Å

  • β = 102.756 (3)°

  • V = 4354.8 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.20 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 = 0.960, Tmax = 0.960

  • 40734 measured reflections

  • 10819 independent reflections

  • 5771 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.201

  • S = 1.04

  • 10819 reflections

  • 571 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.64 e Å−3

  • Δρmin = −0.55 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg5, Cg11 and Cg12 are the centroids of the C27–C31/C36, C1–C5/C10 and C5–C10 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14ACg12i 0.97 3.00 3.951 (2) 168
C16—H16ACg11i 0.97 2.83 3.706 (2) 151
C21—H21⋯Cg11ii 0.93 2.85 3.649 (2) 144
C26—H26BCg5iii 0.96 2.83 3.555 (1) 133
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x, -y+1, -z; (iii) [-x+1, 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).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Nirmala et al., 2009). The pyrrolizine ring system is folded about the bridging N1—C17 bond for molecule (I) and N2—C43 bond for molecule (II), as observed in related structures (Ramesh et al., 2007; Nirmala et al., 2009). The dihedral angle between the naphthalene ring system and the chlorophenyl substituent is 58.76 (9) ° for molecule (I) and 51.59 (8) ° for molecule (II).

In the pyrrolizine ring system, both the pyrrolidine rings [N1/C14—C17, N1/C11/C12/C18/C17 for molecule (I) and N2/C40—C43, N2/C37/C38/C44/C43 for molecule (II)] adopt envelope conformations with the puckering parameters (Cremer and Pople, 1975) q2 = 0.3852 (2) Å and ϕ 2 = 257.36 (2)° and q2 = 0.3627 (2) Å and ϕ 2 = 71.35 (2)° respectively for molecule (I), q2 = 0.4343 (2) Å and ϕ 2 = 242.94 (2) ° & q2 = 0.3354 (2) Å and ϕ 2 = 89.25 (2) ° respectively for molecule (II).

The six-membered heterocyclic ring [C8/C9/C11/C12/C13/O1 for molecule (I) and C34/C35/C37/C38/C39/O4 for molecule (II)] of the benzochromenopyrrole moiety adopts a half-chair conformation with the puckering parameters (Cremer and Pople, 1975) Q = 0.4529 (2) Å, Θ = 132.97 (2) ° and ϕ = 78.47 (2) ° for molecule (I) and Q = 0.4706 (2) Å, Θ = 132.03 (2) ° and ϕ = 93.57 (2) ° for molecule (II) respectively. The sum of bond angles around N1 [334.10 (2) °] for molecule (I) and N2 [334.40 (2) °] for molecule (II) indicates the sp3 hybridization state of atoms N1 & N2.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak C—H···π interactions[C14—H14A···Cg12(-X, -1/2+Y, 1/2-Z) distance of 3.951 (2) Å, C16—H16A···Cg11(-X, -1/2+Y, 1/2-Z) distance of 3.706 (2) Å, C21—H21···Cg11(-X, 1-Y, -Z) distance of 3.649 (2) Å and C26—H26B···Cg5 (1-X, 1/2+Y, 1/2-Z) distance of 3.555 (1) Å (Cg5, Cg11 & Cg12 are the centroid of the rings defined by the atoms C27/C28/C29/C30/C31/C36, C1/C2/C3/C4/C5/C10 & C5/C6/C7/C8/C9/C10 respectively)].

Related literature top

For the biological activity of chromenopyrroles, see: Caine (1993); Tidey (1992); Carlson (1993); Sokoloff et al. (1990); Wilner (1985). For a related structure, see: Nirmala et al. (2009). For general background, see: Ramesh et al. (2007). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of (Z)-methyl 2-((1-formylnaphthalen-2-yloxy) methyl) -3-(4-chloro phenylacrylate (20 mmol) and proline (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 by slow evaporation method.

Refinement top

The site occupancy factors of a disordered C atom were refined as C41 = 0.69 (2) and C41A = 0.31 (2) during anisotropic refinement. H atoms were positioned geometrically and refined using riding model with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic, C—H = 0.98Å and Uiso(H) = 1.2Ueq(C) for methine, C—H = 0.97Å and Uiso(H) = 1.2Ueq(C) for methylene , C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for methyl groups. The components of the anisotropic displacement parameters in direction of the bond of C22 and C23, were restrained to be equal within an effective standard deviation of 0.001 using the DELU command in SHELXL97(Sheldrick, 2008).

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) and (II), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Methyl 4-(4-chlorophenyl)-1,2,3,3a,4,4a,5,12c- octahydrobenzo[f]chromeno[3,4-b]pyrrolizine-4a-carboxylate top
Crystal data top
C26H24ClNO3F(000) = 1824
Mr = 433.91Dx = 1.324 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6164 reflections
a = 22.3214 (9) Åθ = 2.5–28.0°
b = 10.8122 (5) ŵ = 0.20 mm1
c = 18.5008 (8) ÅT = 295 K
β = 102.756 (3)°Block, colourless
V = 4354.8 (3) Å30.20 × 0.20 × 0.20 mm
Z = 8
Data collection top
Bruker Kappa APEXII
diffractometer
10819 independent reflections
Radiation source: fine-focus sealed tube5771 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 0 pixels mm-1θmax = 28.3°, θmin = 0.9°
ω and ϕ scansh = 2929
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.960, Tmax = 0.960l = 2424
40734 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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0823P)2 + 1.6776P]
where P = (Fo2 + 2Fc2)/3
10819 reflections(Δ/σ)max = 0.031
571 parametersΔρmax = 0.64 e Å3
1 restraintΔρmin = 0.55 e Å3
Crystal data top
C26H24ClNO3V = 4354.8 (3) Å3
Mr = 433.91Z = 8
Monoclinic, P21/cMo Kα radiation
a = 22.3214 (9) ŵ = 0.20 mm1
b = 10.8122 (5) ÅT = 295 K
c = 18.5008 (8) Å0.20 × 0.20 × 0.20 mm
β = 102.756 (3)°
Data collection top
Bruker Kappa APEXII
diffractometer
10819 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5771 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.960Rint = 0.040
40734 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0631 restraint
wR(F2) = 0.201H-atom parameters constrained
S = 1.04Δρmax = 0.64 e Å3
10819 reflectionsΔρmin = 0.55 e Å3
571 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.07636 (12)0.0026 (3)0.73870 (14)0.0533 (6)
H10.04700.06510.74700.064*
C20.12729 (14)0.0129 (3)0.76812 (16)0.0641 (8)
H20.13220.08230.79600.077*
C30.17171 (14)0.0793 (3)0.75678 (17)0.0694 (9)
H30.20680.07010.77560.083*
C40.16401 (13)0.1825 (3)0.71836 (16)0.0631 (8)
H40.19360.24450.71190.076*
C50.11179 (12)0.1972 (3)0.68793 (14)0.0506 (6)
C60.10198 (13)0.3072 (3)0.65035 (15)0.0581 (7)
H60.13060.37090.64520.070*
C70.05150 (12)0.3204 (2)0.62199 (15)0.0539 (6)
H70.04490.39400.59900.065*
C80.00902 (11)0.2231 (2)0.62717 (13)0.0455 (6)
C90.01553 (11)0.1132 (2)0.66223 (12)0.0431 (5)
C100.06751 (11)0.1020 (2)0.69571 (12)0.0450 (6)
C110.03076 (10)0.0100 (2)0.66425 (13)0.0425 (5)
H110.04130.02520.71430.051*
C120.08965 (11)0.0557 (2)0.64277 (13)0.0447 (6)
C130.07239 (11)0.1440 (2)0.57766 (13)0.0474 (6)
H13A0.04720.10080.53590.057*
H13B0.10940.17170.56320.057*
C140.02061 (14)0.1973 (2)0.63721 (16)0.0601 (7)
H14A0.00450.20970.68990.072*
H14B0.06480.18670.62830.072*
C150.00443 (14)0.3051 (3)0.59322 (16)0.0606 (7)
H15A0.03230.31030.54500.073*
H15B0.00560.38250.61940.073*
C160.05997 (14)0.2756 (3)0.58591 (17)0.0636 (8)
H16A0.09000.30210.62950.076*
H16B0.06910.31500.54250.076*
C170.05954 (11)0.1360 (2)0.57842 (15)0.0516 (6)
H170.05110.11470.52570.062*
C180.11705 (11)0.0657 (3)0.61847 (14)0.0507 (6)
H180.13490.11200.66360.061*
C190.16677 (12)0.0508 (3)0.57547 (15)0.0538 (6)
C200.15403 (14)0.0320 (3)0.49928 (16)0.0648 (8)
H200.11330.02940.47320.078*
C210.20021 (16)0.0171 (3)0.46145 (19)0.0745 (9)
H210.19060.00330.41060.089*
C220.25994 (16)0.0226 (3)0.4986 (2)0.0781 (9)
C230.27455 (15)0.0397 (4)0.5730 (2)0.0866 (10)
H230.31550.04170.59820.104*
C240.22811 (13)0.0542 (3)0.61148 (19)0.0744 (9)
H240.23850.06650.66250.089*
C250.13534 (11)0.1199 (3)0.70353 (14)0.0497 (6)
C260.17634 (18)0.1413 (4)0.83147 (17)0.0989 (13)
H26A0.17570.22980.82670.148*
H26B0.16690.11890.87790.148*
H26C0.21640.11080.82970.148*
C270.27507 (12)0.1797 (3)1.01938 (14)0.0554 (7)
H270.29770.25161.01830.067*
C280.22600 (14)0.1821 (3)1.05207 (16)0.0714 (9)
H280.21590.25511.07310.086*
C290.19090 (15)0.0768 (4)1.05429 (18)0.0810 (10)
H290.15750.07931.07670.097*
C300.20549 (14)0.0296 (4)1.02362 (17)0.0747 (9)
H300.18220.10021.02590.090*
C310.25532 (12)0.0358 (3)0.98824 (14)0.0561 (7)
C320.26886 (14)0.1441 (3)0.95261 (17)0.0656 (8)
H320.24540.21480.95380.079*
C330.31533 (14)0.1470 (3)0.91679 (17)0.0636 (7)
H330.32300.21870.89250.076*
C340.35220 (12)0.0419 (3)0.91605 (14)0.0513 (6)
C350.34343 (11)0.0648 (2)0.95212 (13)0.0454 (6)
C360.29225 (11)0.0707 (2)0.98716 (13)0.0464 (6)
C370.38691 (12)0.1712 (2)0.95372 (14)0.0503 (6)
H370.36480.24980.95170.060*
C380.42144 (11)0.1641 (3)0.89047 (14)0.0515 (6)
C390.44475 (12)0.0338 (3)0.88659 (15)0.0552 (7)
H39A0.47460.01550.93200.066*
H39B0.46550.02790.84580.066*
C400.42860 (16)0.2218 (4)1.08863 (17)0.0810 (10)
H40A0.39240.27411.07870.097*
H40B0.42300.15751.12310.097*
C420.5073 (2)0.3374 (4)1.05483 (19)0.0912 (12)
H42A0.48610.41141.03310.109*
H42B0.55120.35331.06760.109*
C430.49248 (15)0.2293 (3)1.00385 (17)0.0700 (8)
H430.52720.17161.01430.084*
C440.47562 (13)0.2556 (3)0.91870 (16)0.0611 (7)
H440.45910.33980.91170.073*
C450.52890 (12)0.2479 (3)0.88104 (14)0.0521 (6)
C460.57228 (13)0.1541 (3)0.89731 (17)0.0672 (8)
H460.56940.09660.93380.081*
C470.61934 (13)0.1444 (3)0.86064 (18)0.0711 (9)
H470.64770.08040.87170.085*
C480.62386 (13)0.2299 (3)0.80779 (17)0.0690 (8)
C490.58322 (14)0.3254 (3)0.79190 (17)0.0719 (9)
H490.58770.38510.75720.086*
C500.53543 (13)0.3326 (3)0.82786 (16)0.0633 (8)
H500.50690.39620.81590.076*
C510.38363 (13)0.2008 (3)0.81484 (17)0.0628 (7)
C520.3130 (2)0.3414 (5)0.7477 (2)0.1147 (15)
H52A0.29330.27280.71910.172*
H52B0.28240.39820.75680.172*
H52C0.33940.38270.72100.172*
N10.00836 (9)0.08961 (18)0.61034 (11)0.0453 (5)
N20.43864 (10)0.1676 (2)1.02015 (12)0.0621 (6)
O10.03955 (8)0.24894 (16)0.59566 (10)0.0536 (4)
O20.17254 (10)0.1925 (2)0.69264 (11)0.0794 (7)
O30.13110 (10)0.0879 (2)0.77133 (10)0.0796 (7)
O40.39666 (9)0.05623 (18)0.87646 (11)0.0625 (5)
O50.38716 (15)0.1522 (3)0.75852 (13)0.1160 (10)
O60.34906 (11)0.2967 (2)0.81782 (12)0.0883 (7)
Cl10.31782 (5)0.00823 (10)0.44984 (8)0.1211 (5)
Cl20.68286 (5)0.21687 (13)0.76101 (7)0.1163 (4)
C410.4847 (5)0.2963 (9)1.1198 (4)0.077 (2)0.69 (2)
H41A0.51530.24621.15230.092*0.69 (2)
H41B0.47460.36661.14740.092*0.69 (2)
C41A0.4516 (12)0.3365 (15)1.0949 (12)0.080 (5)0.31 (2)
H41C0.42060.39541.07170.096*0.31 (2)
H41D0.46560.35851.14670.096*0.31 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0563 (15)0.0537 (16)0.0517 (14)0.0058 (13)0.0160 (12)0.0046 (13)
C20.0726 (19)0.0651 (19)0.0601 (17)0.0156 (16)0.0267 (15)0.0091 (14)
C30.0559 (17)0.087 (2)0.0709 (19)0.0122 (17)0.0256 (15)0.0190 (18)
C40.0485 (15)0.074 (2)0.0658 (17)0.0056 (14)0.0099 (13)0.0191 (16)
C50.0484 (14)0.0522 (16)0.0482 (13)0.0007 (12)0.0039 (11)0.0109 (12)
C60.0570 (16)0.0504 (16)0.0621 (16)0.0125 (13)0.0027 (13)0.0094 (14)
C70.0607 (16)0.0391 (14)0.0580 (15)0.0042 (12)0.0046 (13)0.0008 (12)
C80.0466 (13)0.0433 (14)0.0441 (13)0.0030 (11)0.0050 (10)0.0010 (11)
C90.0431 (13)0.0435 (14)0.0396 (12)0.0019 (11)0.0022 (10)0.0007 (10)
C100.0467 (13)0.0461 (14)0.0397 (12)0.0045 (11)0.0041 (10)0.0065 (11)
C110.0430 (12)0.0414 (13)0.0401 (12)0.0009 (11)0.0028 (10)0.0042 (10)
C120.0404 (12)0.0469 (14)0.0452 (13)0.0007 (11)0.0056 (10)0.0050 (11)
C130.0450 (13)0.0482 (14)0.0489 (13)0.0010 (11)0.0102 (11)0.0073 (12)
C140.0701 (18)0.0437 (15)0.0685 (17)0.0104 (14)0.0196 (14)0.0036 (13)
C150.078 (2)0.0399 (14)0.0595 (16)0.0069 (14)0.0053 (14)0.0064 (13)
C160.0706 (19)0.0463 (16)0.0682 (18)0.0064 (14)0.0032 (15)0.0058 (14)
C170.0484 (14)0.0508 (15)0.0532 (14)0.0007 (12)0.0062 (12)0.0016 (12)
C180.0444 (13)0.0535 (16)0.0518 (14)0.0036 (12)0.0053 (11)0.0051 (12)
C190.0455 (14)0.0514 (16)0.0641 (17)0.0019 (12)0.0113 (12)0.0039 (13)
C200.0602 (17)0.073 (2)0.0630 (18)0.0105 (15)0.0176 (14)0.0129 (15)
C210.084 (2)0.072 (2)0.076 (2)0.0168 (18)0.0353 (18)0.0229 (17)
C220.072 (2)0.0567 (19)0.119 (2)0.0069 (16)0.050 (2)0.0200 (19)
C230.0443 (17)0.088 (3)0.127 (2)0.0065 (17)0.0175 (19)0.003 (2)
C240.0461 (16)0.088 (2)0.085 (2)0.0089 (16)0.0061 (15)0.0102 (19)
C250.0447 (14)0.0540 (16)0.0474 (14)0.0028 (12)0.0036 (11)0.0038 (12)
C260.108 (3)0.115 (3)0.0555 (18)0.041 (3)0.0202 (19)0.007 (2)
C270.0509 (15)0.0674 (18)0.0502 (14)0.0046 (13)0.0160 (12)0.0017 (13)
C280.0662 (19)0.091 (2)0.0635 (18)0.0082 (18)0.0277 (15)0.0031 (17)
C290.070 (2)0.116 (3)0.068 (2)0.002 (2)0.0381 (17)0.001 (2)
C300.0666 (19)0.094 (3)0.0678 (19)0.0193 (18)0.0241 (16)0.0140 (19)
C310.0545 (16)0.0656 (19)0.0474 (14)0.0027 (14)0.0093 (12)0.0116 (13)
C320.0655 (18)0.0573 (18)0.0724 (19)0.0120 (15)0.0122 (15)0.0107 (15)
C330.0723 (19)0.0487 (16)0.0681 (18)0.0009 (15)0.0118 (15)0.0030 (14)
C340.0491 (14)0.0536 (16)0.0511 (14)0.0029 (12)0.0107 (12)0.0007 (12)
C350.0436 (13)0.0488 (14)0.0435 (13)0.0030 (11)0.0091 (10)0.0038 (11)
C360.0441 (13)0.0550 (16)0.0396 (12)0.0003 (12)0.0079 (10)0.0060 (11)
C370.0530 (15)0.0497 (15)0.0529 (14)0.0006 (12)0.0218 (12)0.0035 (12)
C380.0482 (14)0.0588 (17)0.0509 (14)0.0023 (13)0.0182 (12)0.0007 (12)
C390.0483 (14)0.0633 (18)0.0562 (15)0.0002 (13)0.0165 (12)0.0087 (13)
C400.080 (2)0.112 (3)0.0537 (17)0.014 (2)0.0214 (16)0.0244 (19)
C420.119 (3)0.076 (2)0.070 (2)0.036 (2)0.005 (2)0.0069 (18)
C430.073 (2)0.078 (2)0.0632 (17)0.0127 (17)0.0224 (15)0.0039 (16)
C440.0578 (16)0.0643 (18)0.0666 (17)0.0092 (14)0.0251 (14)0.0030 (15)
C450.0490 (14)0.0588 (16)0.0496 (14)0.0066 (13)0.0134 (11)0.0037 (13)
C460.0606 (17)0.075 (2)0.0661 (18)0.0013 (16)0.0133 (14)0.0255 (16)
C470.0482 (16)0.078 (2)0.086 (2)0.0123 (15)0.0132 (15)0.0168 (18)
C480.0539 (17)0.089 (2)0.0698 (19)0.0023 (17)0.0254 (14)0.0062 (18)
C490.074 (2)0.083 (2)0.0637 (18)0.0030 (18)0.0258 (16)0.0267 (17)
C500.0580 (16)0.0649 (19)0.0680 (18)0.0074 (14)0.0159 (14)0.0148 (15)
C510.0601 (17)0.073 (2)0.0603 (17)0.0082 (15)0.0238 (14)0.0043 (16)
C520.109 (3)0.126 (4)0.105 (3)0.038 (3)0.014 (3)0.046 (3)
N10.0470 (11)0.0398 (11)0.0488 (11)0.0032 (9)0.0102 (9)0.0035 (9)
N20.0550 (13)0.0814 (18)0.0520 (12)0.0137 (12)0.0163 (11)0.0146 (12)
O10.0583 (11)0.0422 (10)0.0610 (11)0.0004 (8)0.0149 (9)0.0101 (8)
O20.0765 (14)0.0942 (17)0.0653 (12)0.0387 (13)0.0108 (11)0.0031 (12)
O30.0849 (15)0.0937 (17)0.0486 (11)0.0366 (13)0.0099 (10)0.0138 (11)
O40.0589 (11)0.0575 (12)0.0757 (13)0.0010 (9)0.0248 (10)0.0177 (10)
O50.150 (3)0.135 (3)0.0572 (14)0.053 (2)0.0100 (15)0.0066 (15)
O60.1044 (18)0.0896 (17)0.0706 (14)0.0384 (15)0.0188 (13)0.0166 (13)
Cl10.1133 (8)0.0878 (7)0.1952 (13)0.0268 (6)0.1052 (9)0.0392 (7)
Cl20.0892 (7)0.1540 (11)0.1256 (9)0.0129 (7)0.0664 (6)0.0095 (8)
C410.096 (6)0.072 (4)0.057 (3)0.006 (4)0.007 (3)0.005 (3)
C41A0.109 (13)0.061 (8)0.066 (9)0.010 (8)0.009 (9)0.023 (6)
Geometric parameters (Å, º) top
C1—C21.369 (4)C27—H270.9300
C1—C101.421 (4)C28—C291.388 (5)
C1—H10.9300C28—H280.9300
C2—C31.389 (4)C29—C301.354 (5)
C2—H20.9300C29—H290.9300
C3—C41.354 (4)C30—C311.411 (4)
C3—H30.9300C30—H300.9300
C4—C51.411 (4)C31—C321.409 (4)
C4—H40.9300C31—C361.419 (4)
C5—C101.412 (4)C32—C331.349 (4)
C5—C61.418 (4)C32—H320.9300
C6—C71.351 (4)C33—C341.405 (4)
C6—H60.9300C33—H330.9300
C7—C81.405 (4)C34—O41.366 (3)
C7—H70.9300C34—C351.369 (4)
C8—O11.368 (3)C35—C361.434 (3)
C8—C91.376 (3)C35—C371.501 (4)
C9—C101.436 (3)C37—N21.489 (4)
C9—C111.516 (3)C37—C381.539 (3)
C11—N11.478 (3)C37—H370.9800
C11—C121.536 (3)C38—C391.509 (4)
C11—H110.9800C38—C511.518 (4)
C12—C251.510 (3)C38—C441.561 (4)
C12—C131.519 (3)C39—O41.430 (3)
C12—C181.555 (4)C39—H39A0.9700
C13—O11.429 (3)C39—H39B0.9700
C13—H13A0.9700C40—C41A1.338 (14)
C13—H13B0.9700C40—N21.457 (4)
C14—N11.471 (3)C40—C411.493 (8)
C14—C151.510 (4)C40—H40A0.9700
C14—H14A0.9700C40—H40B0.9700
C14—H14B0.9700C42—C411.471 (7)
C15—C161.507 (4)C42—C431.492 (5)
C15—H15A0.9700C42—C41A1.582 (17)
C15—H15B0.9700C42—H42A0.9700
C16—C171.516 (4)C42—H42B0.9700
C16—H16A0.9700C43—N21.463 (4)
C16—H16B0.9700C43—C441.563 (4)
C17—N11.484 (3)C43—H430.9800
C17—C181.535 (4)C44—C451.507 (4)
C17—H170.9800C44—H440.9800
C18—C191.510 (3)C45—C501.375 (4)
C18—H180.9800C45—C461.388 (4)
C19—C241.385 (4)C46—C471.375 (4)
C19—C201.390 (4)C46—H460.9300
C20—C211.377 (4)C47—C481.365 (4)
C20—H200.9300C47—H470.9300
C21—C221.360 (5)C48—C491.364 (4)
C21—H210.9300C48—Cl21.734 (3)
C22—C231.355 (5)C49—C501.378 (4)
C22—Cl11.739 (3)C49—H490.9300
C23—C241.390 (4)C50—H500.9300
C23—H230.9300C51—O51.185 (3)
C24—H240.9300C51—O61.301 (4)
C25—O21.192 (3)C52—O61.450 (4)
C25—O31.325 (3)C52—H52A0.9600
C26—O31.448 (4)C52—H52B0.9600
C26—H26A0.9600C52—H52C0.9600
C26—H26B0.9600C41—H41A0.9700
C26—H26C0.9600C41—H41B0.9700
C27—C281.363 (4)C41A—H41C0.9700
C27—C361.411 (4)C41A—H41D0.9700
C2—C1—C10121.2 (3)C32—C31—C30121.9 (3)
C2—C1—H1119.4C32—C31—C36118.9 (2)
C10—C1—H1119.4C30—C31—C36119.2 (3)
C1—C2—C3120.6 (3)C33—C32—C31121.1 (3)
C1—C2—H2119.7C33—C32—H32119.4
C3—C2—H2119.7C31—C32—H32119.4
C4—C3—C2120.1 (3)C32—C33—C34120.1 (3)
C4—C3—H3119.9C32—C33—H33120.0
C2—C3—H3119.9C34—C33—H33120.0
C3—C4—C5121.0 (3)O4—C34—C35123.8 (2)
C3—C4—H4119.5O4—C34—C33114.2 (2)
C5—C4—H4119.5C35—C34—C33122.0 (2)
C4—C5—C10119.9 (3)C34—C35—C36118.2 (2)
C4—C5—C6121.4 (3)C34—C35—C37119.6 (2)
C10—C5—C6118.7 (2)C36—C35—C37122.2 (2)
C7—C6—C5120.8 (3)C27—C36—C31117.3 (2)
C7—C6—H6119.6C27—C36—C35123.1 (2)
C5—C6—H6119.6C31—C36—C35119.6 (2)
C6—C7—C8120.1 (3)N2—C37—C35112.1 (2)
C6—C7—H7119.9N2—C37—C38101.48 (19)
C8—C7—H7119.9C35—C37—C38112.2 (2)
O1—C8—C9123.6 (2)N2—C37—H37110.3
O1—C8—C7113.8 (2)C35—C37—H37110.3
C9—C8—C7122.6 (2)C38—C37—H37110.3
C8—C9—C10117.1 (2)C39—C38—C51109.1 (2)
C8—C9—C11120.3 (2)C39—C38—C37108.6 (2)
C10—C9—C11122.6 (2)C51—C38—C37114.7 (2)
C5—C10—C1117.2 (2)C39—C38—C44111.0 (2)
C5—C10—C9120.6 (2)C51—C38—C44112.0 (2)
C1—C10—C9122.3 (2)C37—C38—C44101.3 (2)
N1—C11—C9113.13 (18)O4—C39—C38112.6 (2)
N1—C11—C12103.94 (18)O4—C39—H39A109.1
C9—C11—C12112.0 (2)C38—C39—H39A109.1
N1—C11—H11109.2O4—C39—H39B109.1
C9—C11—H11109.2C38—C39—H39B109.1
C12—C11—H11109.2H39A—C39—H39B107.8
C25—C12—C13108.2 (2)C41A—C40—N2108.5 (6)
C25—C12—C11115.5 (2)C41A—C40—C4136.2 (9)
C13—C12—C11109.01 (19)N2—C40—C41106.0 (3)
C25—C12—C18111.1 (2)C41A—C40—H40A76.4
C13—C12—C18110.4 (2)N2—C40—H40A110.5
C11—C12—C18102.53 (19)C41—C40—H40A110.5
O1—C13—C12111.57 (19)C41A—C40—H40B135.2
O1—C13—H13A109.3N2—C40—H40B110.5
C12—C13—H13A109.3C41—C40—H40B110.5
O1—C13—H13B109.3H40A—C40—H40B108.7
C12—C13—H13B109.3C41—C42—C43102.2 (3)
H13A—C13—H13B108.0C41—C42—C41A33.7 (6)
N1—C14—C15104.7 (2)C43—C42—C41A101.7 (5)
N1—C14—H14A110.8C41—C42—H42A111.3
C15—C14—H14A110.8C43—C42—H42A111.3
N1—C14—H14B110.8C41A—C42—H42A80.7
C15—C14—H14B110.8C41—C42—H42B111.3
H14A—C14—H14B108.9C43—C42—H42B111.3
C16—C15—C14103.4 (2)C41A—C42—H42B137.9
C16—C15—H15A111.1H42A—C42—H42B109.2
C14—C15—H15A111.1N2—C43—C42107.7 (3)
C16—C15—H15B111.1N2—C43—C44105.3 (2)
C14—C15—H15B111.1C42—C43—C44117.7 (3)
H15A—C15—H15B109.1N2—C43—H43108.6
C15—C16—C17103.4 (2)C42—C43—H43108.6
C15—C16—H16A111.1C44—C43—H43108.6
C17—C16—H16A111.1C45—C44—C38116.3 (2)
C15—C16—H16B111.1C45—C44—C43114.6 (2)
C17—C16—H16B111.1C38—C44—C43102.6 (2)
H16A—C16—H16B109.0C45—C44—H44107.6
N1—C17—C16106.9 (2)C38—C44—H44107.6
N1—C17—C18106.0 (2)C43—C44—H44107.6
C16—C17—C18117.5 (2)C50—C45—C46117.5 (2)
N1—C17—H17108.7C50—C45—C44120.9 (3)
C16—C17—H17108.7C46—C45—C44121.6 (2)
C18—C17—H17108.7C47—C46—C45121.4 (3)
C19—C18—C17115.6 (2)C47—C46—H46119.3
C19—C18—C12116.4 (2)C45—C46—H46119.3
C17—C18—C12102.54 (19)C48—C47—C46119.2 (3)
C19—C18—H18107.3C48—C47—H47120.4
C17—C18—H18107.3C46—C47—H47120.4
C12—C18—H18107.3C49—C48—C47121.1 (3)
C24—C19—C20116.8 (3)C49—C48—Cl2119.8 (2)
C24—C19—C18120.5 (3)C47—C48—Cl2119.2 (3)
C20—C19—C18122.7 (2)C48—C49—C50119.2 (3)
C21—C20—C19121.6 (3)C48—C49—H49120.4
C21—C20—H20119.2C50—C49—H49120.4
C19—C20—H20119.2C45—C50—C49121.6 (3)
C22—C21—C20119.9 (3)C45—C50—H50119.2
C22—C21—H21120.1C49—C50—H50119.2
C20—C21—H21120.1O5—C51—O6123.1 (3)
C23—C22—C21120.6 (3)O5—C51—C38124.3 (3)
C23—C22—Cl1120.0 (3)O6—C51—C38112.5 (3)
C21—C22—Cl1119.4 (3)O6—C52—H52A109.5
C22—C23—C24119.7 (3)O6—C52—H52B109.5
C22—C23—H23120.1H52A—C52—H52B109.5
C24—C23—H23120.1O6—C52—H52C109.5
C19—C24—C23121.4 (3)H52A—C52—H52C109.5
C19—C24—H24119.3H52B—C52—H52C109.5
C23—C24—H24119.3C14—N1—C11117.21 (19)
O2—C25—O3122.1 (2)C14—N1—C17107.5 (2)
O2—C25—C12124.0 (2)C11—N1—C17109.84 (18)
O3—C25—C12114.0 (2)C40—N2—C43106.7 (2)
O3—C26—H26A109.5C40—N2—C37117.8 (2)
O3—C26—H26B109.5C43—N2—C37109.9 (2)
H26A—C26—H26B109.5C8—O1—C13115.63 (19)
O3—C26—H26C109.5C25—O3—C26116.1 (2)
H26A—C26—H26C109.5C34—O4—C39117.8 (2)
H26B—C26—H26C109.5C51—O6—C52116.4 (3)
C28—C27—C36121.5 (3)C42—C41—C40105.0 (5)
C28—C27—H27119.2C42—C41—H41A110.8
C36—C27—H27119.2C40—C41—H41A110.8
C27—C28—C29120.8 (3)C42—C41—H41B110.8
C27—C28—H28119.6C40—C41—H41B110.8
C29—C28—H28119.6H41A—C41—H41B108.8
C30—C29—C28119.7 (3)C40—C41A—C42107.0 (10)
C30—C29—H29120.2C40—C41A—H41C110.3
C28—C29—H29120.2C42—C41A—H41C110.3
C29—C30—C31121.4 (3)C40—C41A—H41D110.3
C29—C30—H30119.3C42—C41A—H41D110.3
C31—C30—H30119.3H41C—C41A—H41D108.6
C10—C1—C2—C30.2 (4)C34—C35—C36—C27173.4 (2)
C1—C2—C3—C42.1 (5)C37—C35—C36—C276.4 (4)
C2—C3—C4—C51.4 (4)C34—C35—C36—C314.6 (3)
C3—C4—C5—C101.7 (4)C37—C35—C36—C31175.6 (2)
C3—C4—C5—C6177.3 (3)C34—C35—C37—N291.9 (3)
C4—C5—C6—C7179.5 (2)C36—C35—C37—N288.3 (3)
C10—C5—C6—C70.5 (4)C34—C35—C37—C3821.6 (3)
C5—C6—C7—C82.3 (4)C36—C35—C37—C38158.2 (2)
C6—C7—C8—O1179.5 (2)N2—C37—C38—C3973.7 (3)
C6—C7—C8—C91.7 (4)C35—C37—C38—C3946.2 (3)
O1—C8—C9—C10177.1 (2)N2—C37—C38—C51164.0 (2)
C7—C8—C9—C101.5 (3)C35—C37—C38—C5176.2 (3)
O1—C8—C9—C113.2 (4)N2—C37—C38—C4443.2 (3)
C7—C8—C9—C11178.2 (2)C35—C37—C38—C44163.0 (2)
C4—C5—C10—C13.9 (3)C51—C38—C39—O468.7 (3)
C6—C5—C10—C1175.1 (2)C37—C38—C39—O457.0 (3)
C4—C5—C10—C9177.2 (2)C44—C38—C39—O4167.5 (2)
C6—C5—C10—C93.8 (3)C41—C42—C43—N228.8 (7)
C2—C1—C10—C53.2 (4)C41A—C42—C43—N25.7 (11)
C2—C1—C10—C9177.9 (2)C41—C42—C43—C44147.6 (6)
C8—C9—C10—C54.3 (3)C41A—C42—C43—C44113.1 (11)
C11—C9—C10—C5175.5 (2)C39—C38—C44—C4549.2 (3)
C8—C9—C10—C1174.6 (2)C51—C38—C44—C4573.0 (3)
C11—C9—C10—C15.6 (3)C37—C38—C44—C45164.3 (2)
C8—C9—C11—N1102.2 (2)C39—C38—C44—C4376.8 (3)
C10—C9—C11—N177.5 (3)C51—C38—C44—C43161.0 (2)
C8—C9—C11—C1214.9 (3)C37—C38—C44—C4338.3 (3)
C10—C9—C11—C12165.4 (2)N2—C43—C44—C45146.1 (3)
N1—C11—C12—C25157.0 (2)C42—C43—C44—C4593.8 (4)
C9—C11—C12—C2580.6 (3)N2—C43—C44—C3819.1 (3)
N1—C11—C12—C1380.9 (2)C42—C43—C44—C38139.2 (3)
C9—C11—C12—C1341.5 (3)C38—C44—C45—C50101.4 (3)
N1—C11—C12—C1836.0 (2)C43—C44—C45—C50139.0 (3)
C9—C11—C12—C18158.50 (19)C38—C44—C45—C4677.1 (4)
C25—C12—C13—O166.2 (2)C43—C44—C45—C4642.5 (4)
C11—C12—C13—O160.2 (3)C50—C45—C46—C471.3 (5)
C18—C12—C13—O1172.10 (19)C44—C45—C46—C47177.2 (3)
N1—C14—C15—C1636.6 (3)C45—C46—C47—C480.9 (5)
C14—C15—C16—C1735.5 (3)C46—C47—C48—C491.2 (5)
C15—C16—C17—N121.8 (3)C46—C47—C48—Cl2179.5 (3)
C15—C16—C17—C18140.6 (2)C47—C48—C49—C502.6 (5)
N1—C17—C18—C19153.3 (2)Cl2—C48—C49—C50178.0 (3)
C16—C17—C18—C1987.4 (3)C46—C45—C50—C490.2 (4)
N1—C17—C18—C1225.6 (2)C44—C45—C50—C49178.7 (3)
C16—C17—C18—C12144.9 (2)C48—C49—C50—C452.1 (5)
C25—C12—C18—C1971.1 (3)C39—C38—C51—O520.7 (4)
C13—C12—C18—C1948.9 (3)C37—C38—C51—O5142.7 (3)
C11—C12—C18—C19164.9 (2)C44—C38—C51—O5102.6 (4)
C25—C12—C18—C17161.7 (2)C39—C38—C51—O6163.0 (2)
C13—C12—C18—C1778.3 (2)C37—C38—C51—O641.0 (4)
C11—C12—C18—C1737.7 (2)C44—C38—C51—O673.7 (3)
C17—C18—C19—C24144.5 (3)C15—C14—N1—C11147.4 (2)
C12—C18—C19—C2495.1 (3)C15—C14—N1—C1723.1 (3)
C17—C18—C19—C2036.2 (4)C9—C11—N1—C1494.5 (3)
C12—C18—C19—C2084.2 (3)C12—C11—N1—C14143.8 (2)
C24—C19—C20—C210.2 (5)C9—C11—N1—C17142.5 (2)
C18—C19—C20—C21179.2 (3)C12—C11—N1—C1720.8 (2)
C19—C20—C21—C221.0 (5)C16—C17—N1—C140.8 (3)
C20—C21—C22—C231.6 (5)C18—C17—N1—C14125.3 (2)
C20—C21—C22—Cl1178.1 (2)C16—C17—N1—C11129.4 (2)
C21—C22—C23—C241.3 (6)C18—C17—N1—C113.3 (3)
Cl1—C22—C23—C24178.4 (3)C41A—C40—N2—C4326.4 (14)
C20—C19—C24—C230.1 (5)C41—C40—N2—C4311.5 (6)
C18—C19—C24—C23179.5 (3)C41A—C40—N2—C3797.7 (14)
C22—C23—C24—C190.4 (5)C41—C40—N2—C37135.6 (6)
C13—C12—C25—O233.3 (4)C42—C43—N2—C4010.8 (4)
C11—C12—C25—O2155.8 (3)C44—C43—N2—C40137.3 (3)
C18—C12—C25—O288.0 (3)C42—C43—N2—C37118.0 (3)
C13—C12—C25—O3147.2 (2)C44—C43—N2—C378.4 (3)
C11—C12—C25—O324.8 (3)C35—C37—N2—C4084.8 (3)
C18—C12—C25—O391.5 (3)C38—C37—N2—C40155.3 (3)
C36—C27—C28—C290.4 (4)C35—C37—N2—C43152.7 (2)
C27—C28—C29—C300.0 (5)C38—C37—N2—C4332.8 (3)
C28—C29—C30—C310.9 (5)C9—C8—O1—C1321.0 (3)
C29—C30—C31—C32176.5 (3)C7—C8—O1—C13160.3 (2)
C29—C30—C31—C362.3 (4)C12—C13—O1—C850.0 (3)
C30—C31—C32—C33177.6 (3)O2—C25—O3—C263.1 (5)
C36—C31—C32—C331.2 (4)C12—C25—O3—C26176.4 (3)
C31—C32—C33—C341.6 (4)C35—C34—O4—C3914.4 (4)
C32—C33—C34—O4178.6 (3)C33—C34—O4—C39165.8 (2)
C32—C33—C34—C351.3 (4)C38—C39—O4—C3441.8 (3)
O4—C34—C35—C36175.5 (2)O5—C51—O6—C521.4 (5)
C33—C34—C35—C364.3 (4)C38—C51—O6—C52177.7 (3)
O4—C34—C35—C374.3 (4)C43—C42—C41—C4035.3 (8)
C33—C34—C35—C37175.9 (2)C41A—C42—C41—C4057.7 (9)
C28—C27—C36—C311.7 (4)C41A—C40—C41—C4269.9 (11)
C28—C27—C36—C35179.8 (2)N2—C40—C41—C4229.8 (9)
C32—C31—C36—C27176.2 (2)N2—C40—C41A—C4230.0 (19)
C30—C31—C36—C272.6 (4)C41—C40—C41A—C4261.9 (14)
C32—C31—C36—C352.0 (4)C41—C42—C41A—C4072.3 (15)
C30—C31—C36—C35179.2 (2)C43—C42—C41A—C4022.1 (18)
Hydrogen-bond geometry (Å, º) top
Cg5, Cg11 and Cg12 are the centroids of the C27–C31/C36, C1–C5/C10 and C5–C10 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11—H11···O30.982.392.773 (3)103
C37—H37···O60.982.482.818 (3)100
C14—H14A···Cg12i0.973.003.951 (2)168
C16—H16A···Cg11i0.972.833.706 (2)151
C21—H21···Cg11ii0.932.853.649 (2)144
C26—H26B···Cg5iii0.962.833.555 (1)133
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+1, z; (iii) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC26H24ClNO3
Mr433.91
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)22.3214 (9), 10.8122 (5), 18.5008 (8)
β (°) 102.756 (3)
V3)4354.8 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.960, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
40734, 10819, 5771
Rint0.040
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.201, 1.04
No. of reflections10819
No. of parameters571
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.64, 0.55

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

Hydrogen-bond geometry (Å, º) top
Cg5, Cg11 and Cg12 are the centroids of the C27–C31/C36, C1–C5/C10 and C5–C10 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11—H11···O30.982.392.773 (3)102.8
C37—H37···O60.982.482.818 (3)100.1
C14—H14A···Cg12i0.973.003.951 (2)168.0
C16—H16A···Cg11i0.972.833.706 (2)151.0
C21—H21···Cg11ii0.932.853.649 (2)144.0
C26—H26B···Cg5iii0.962.833.555 (1)133.0
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+1, z; (iii) x+1, y+1/2, z+1/2.
 

Acknowledgements

BG thanks AMET University management, India, for their kind support.

References

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Volume 66| Part 4| April 2010| Pages o810-o811
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