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

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ISSN: 2056-9890

1′-(4-Bromo­phen­yl)-4′-{4-[(2-oxo-1,2,3,4-tetra­hydro­naphthalen-2-yl­­idene)meth­yl]phen­yl}-3′′,4′′-di­hydro­ace­naphthylene-1-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-2,1′′(1H,2′′H)-dione

aDepartment of Physics, PRIST University, Thanjavur 614 904, Tamil Nadu, India, bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and dDepartment of Research and Development, PRIST University, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: crystallography2010@gmail.com

(Received 4 October 2010; accepted 7 October 2010; online 13 October 2010)

In the title compound, C47H34BrNO3, the central benzene ring makes a dihedral angle of 42.71 (7)° with the bromo­phenyl ring. The pyrrolidine ring adopts an envelope conformation. The mol­ecular structure is stabilized by weak intra­molecular C—H⋯O inter­actions and the crystal packing is stabilized by weak inter­molecular C—H⋯π inter­actions.

Related literature

For the biological activity of pyrrolidine derivatives, see: Amalraj et al. (2003[Amalraj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-419.]); Daly et al. (1986[Daly, J. W., Spande, T. W., Whittaker, N., Highet, R. J., Feigl, D., Noshimori, N., Tokuyama, T. & Meyers, C. W. (1986). J. Nat. Prod. 49, 265-280.]). For related structures, see: Aravindan et al. (2004[Aravindan, P. G., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Sridhar, G. & Raghunathan, R. (2004). Acta Cryst. E60, o2149-o2151.]); Kumar et al. (2006[Kumar, B. K. S., Gayathri, D., Velmurugan, D., Ravikumar, K. & Periyasami, G. (2006). Acta Cryst. E62, o5075-o5077.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C47H34BrNO3

  • Mr = 740.38

  • Triclinic, [P \overline 1]

  • a = 8.4178 (2) Å

  • b = 13.2352 (3) Å

  • c = 15.9610 (3) Å

  • α = 98.143 (1)°

  • β = 92.744 (2)°

  • γ = 100.944 (1)°

  • V = 1723.17 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.24 mm−1

  • T = 295 K

  • 0.20 × 0.19 × 0.18 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.719, Tmax = 0.779

  • 30711 measured reflections

  • 6410 independent reflections

  • 4539 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.03

  • 6410 reflections

  • 469 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.53 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C3–C8 and C12–C17 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C22—H22B⋯O3 0.97 2.55 3.026 (3) 111
C23—H23B⋯O3 0.97 2.40 3.113 (3) 130
C17—H17⋯Cg1i 0.93 2.98 3.720 (3) 137
C26—H26⋯Cg2ii 0.93 3.00 3.925 (3) 178
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y, -z.

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

Highly substituted pyrrolidines have gained much prominence since they form the central skeleton of many natural products (Daly et al., 1986). Substituted pyrrolidine compounds possess antimicrobial and antifungal activities against various pathogens (Amalraj et al., 2003).

The geometric parameters of the title compound (Fig. 1) agree well with reported similar structures (Aravindan et al., 2004; Kumar et al., 2006). The benzene ring (C12–C17) makes a dihedral angle of 42.71 (7)° with the bromophenyl ring (C42–C46). The sum of bond angles around N1 [359.9 (2)°] indicates that N1 is sp2-hybridized.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak C—H···π [C17—H17···Cg1 (-1 + x, y, z) distance of 3.720 (3)Å and C26—H26···Cg2 (2 - x, -y, -z) distance of 3.925 (3)Å (Cg1 and Cg2 are the centroid of the rings defined by the atoms C3–C8 and C12–C17, respectively) interactions. The intramolecular interactions C22—H22B···O3 and C23—H23B···O3 generate S(6) and S(7) graph set motifs, respectively (Bernstein et al., 1995).

Related literature top

For the biological activity of pyrrolidine derivatives, see: Amalraj et al. (2003); Daly et al. (1986). For related structures, see: Aravindan et al. (2004); Kumar et al. (2006). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

To the solution of acenaphthequinone (3) (1.1 mmol), N-(p-bromo) phenyl glycine (2) (1.1 mmol) and 1,4-bis(3',4'-dihydro-1'- oxonaphthalen-2'-ylidene)benzene (1) (1.0 mmol) was refluxed in dry toluene. Completion of the reaction was evidenced by TLC analysis. The solvent was then removed in vacuum, diluted in dichloromethane, washed with water, and brine. The organic layer was separated and dried over Na2SO4.The organic solvent was removed and the residue was subjected to column chromatography using hexane/ethyl acetate (6:4) as eluent afforded the cycloadduct.

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.

Structure description top

Highly substituted pyrrolidines have gained much prominence since they form the central skeleton of many natural products (Daly et al., 1986). Substituted pyrrolidine compounds possess antimicrobial and antifungal activities against various pathogens (Amalraj et al., 2003).

The geometric parameters of the title compound (Fig. 1) agree well with reported similar structures (Aravindan et al., 2004; Kumar et al., 2006). The benzene ring (C12–C17) makes a dihedral angle of 42.71 (7)° with the bromophenyl ring (C42–C46). The sum of bond angles around N1 [359.9 (2)°] indicates that N1 is sp2-hybridized.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak C—H···π [C17—H17···Cg1 (-1 + x, y, z) distance of 3.720 (3)Å and C26—H26···Cg2 (2 - x, -y, -z) distance of 3.925 (3)Å (Cg1 and Cg2 are the centroid of the rings defined by the atoms C3–C8 and C12–C17, respectively) interactions. The intramolecular interactions C22—H22B···O3 and C23—H23B···O3 generate S(6) and S(7) graph set motifs, respectively (Bernstein et al., 1995).

For the biological activity of pyrrolidine derivatives, see: Amalraj et al. (2003); Daly et al. (1986). For related structures, see: Aravindan et al. (2004); Kumar et al. (2006). For graph-set notation, see: Bernstein et al. (1995).

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.
1'-(4-Bromophenyl)-4'-{4-[(2-oxo-1,2,3,4-tetrahydronaphthalen-2- ylidene)methyl]phenyl}-3'',4''-dihydroacenaphthylene-1-spiro-2'-pyrrolidine- 3'-spiro-2''-naphthalene-2,1''(1H,2''H)-dione top
Crystal data top
C47H34BrNO3Z = 2
Mr = 740.38F(000) = 764
Triclinic, P1Dx = 1.427 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4178 (2) ÅCell parameters from 8389 reflections
b = 13.2352 (3) Åθ = 2.2–25.3°
c = 15.9610 (3) ŵ = 1.24 mm1
α = 98.143 (1)°T = 295 K
β = 92.744 (2)°Block, colourless
γ = 100.944 (1)°0.20 × 0.19 × 0.18 mm
V = 1723.17 (7) Å3
Data collection top
Bruker Kappa APEXII
diffractometer
6410 independent reflections
Radiation source: fine-focus sealed tube4539 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω and φ scanθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.719, Tmax = 0.779k = 1615
30711 measured reflectionsl = 1919
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0431P)2 + 0.5268P]
where P = (Fo2 + 2Fc2)/3
6410 reflections(Δ/σ)max < 0.001
469 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.53 e Å3
Crystal data top
C47H34BrNO3γ = 100.944 (1)°
Mr = 740.38V = 1723.17 (7) Å3
Triclinic, P1Z = 2
a = 8.4178 (2) ÅMo Kα radiation
b = 13.2352 (3) ŵ = 1.24 mm1
c = 15.9610 (3) ÅT = 295 K
α = 98.143 (1)°0.20 × 0.19 × 0.18 mm
β = 92.744 (2)°
Data collection top
Bruker Kappa APEXII
diffractometer
6410 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4539 reflections with I > 2σ(I)
Tmin = 0.719, Tmax = 0.779Rint = 0.034
30711 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.03Δρmax = 0.32 e Å3
6410 reflectionsΔρmin = 0.53 e Å3
469 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.15843 (4)0.56227 (3)0.415272 (18)0.09413 (16)
O11.4073 (2)0.15001 (17)0.50404 (12)0.0809 (6)
O21.06900 (18)0.31498 (12)0.14876 (10)0.0482 (4)
O30.43369 (19)0.21371 (13)0.13308 (10)0.0546 (4)
N10.6591 (2)0.32198 (14)0.27716 (10)0.0445 (5)
C11.3657 (3)0.08403 (18)0.37579 (14)0.0497 (6)
C21.4467 (3)0.14275 (19)0.43260 (15)0.0538 (6)
C31.5830 (3)0.18953 (17)0.39993 (14)0.0485 (6)
C41.6890 (3)0.2189 (2)0.45546 (16)0.0606 (7)
H41.67330.21030.51310.073*
C51.8182 (4)0.2610 (2)0.42732 (19)0.0724 (8)
H51.89050.27930.46560.087*
C61.8381 (4)0.2753 (2)0.3422 (2)0.0805 (9)
H61.92380.30470.32240.097*
C71.7332 (4)0.2469 (2)0.28582 (18)0.0775 (9)
H71.74830.25770.22810.093*
C81.6049 (3)0.2023 (2)0.31344 (16)0.0605 (7)
C91.4889 (4)0.1689 (3)0.25318 (17)0.0819 (9)
H9A1.54100.15660.20160.098*
H9B1.39420.22430.23810.098*
C101.4366 (4)0.0714 (2)0.29222 (16)0.0660 (7)
H10A1.35640.05470.25360.079*
H10B1.52940.01400.30090.079*
C111.2418 (3)0.04406 (19)0.40358 (15)0.0526 (6)
H111.20520.06390.45400.063*
C121.1534 (3)0.02685 (17)0.36698 (14)0.0453 (5)
C131.2262 (3)0.10465 (17)0.32291 (14)0.0470 (6)
H131.33420.10910.31110.056*
C141.1411 (3)0.17533 (17)0.29635 (14)0.0436 (5)
H141.19330.22690.26750.052*
C150.9800 (3)0.17107 (16)0.31169 (12)0.0387 (5)
C160.9073 (3)0.09371 (19)0.35579 (15)0.0516 (6)
H160.79910.08900.36730.062*
C170.9932 (3)0.02350 (19)0.38283 (15)0.0527 (6)
H170.94150.02730.41250.063*
C180.8906 (3)0.25063 (17)0.28252 (12)0.0383 (5)
H180.96960.31640.28780.046*
C190.8163 (2)0.22580 (15)0.18853 (12)0.0334 (4)
C200.7048 (2)0.31159 (16)0.19066 (12)0.0355 (5)
C210.7503 (3)0.27266 (18)0.33271 (13)0.0455 (5)
H21A0.68490.20870.34530.055*
H21B0.78850.31880.38550.055*
C220.7200 (3)0.11361 (16)0.16731 (13)0.0419 (5)
H22A0.78310.06840.19050.050*
H22B0.62080.10910.19620.050*
C230.6752 (3)0.07172 (18)0.07383 (14)0.0490 (6)
H23A0.63730.00310.06730.059*
H23B0.58630.10180.05430.059*
C240.8125 (3)0.09469 (17)0.01929 (13)0.0417 (5)
C250.8106 (3)0.03584 (19)0.06084 (15)0.0557 (6)
H250.72220.01730.08080.067*
C260.9385 (4)0.0560 (2)0.11032 (16)0.0628 (7)
H260.93480.01750.16410.075*
C271.0711 (3)0.1320 (2)0.08132 (16)0.0593 (7)
H271.15810.14400.11480.071*
C281.0759 (3)0.19022 (17)0.00322 (14)0.0475 (6)
H281.16710.24110.01680.057*
C290.9446 (3)0.17386 (16)0.04690 (13)0.0379 (5)
C300.9538 (3)0.24389 (16)0.12859 (13)0.0362 (5)
C310.7872 (2)0.41129 (16)0.16111 (13)0.0371 (5)
C320.9035 (3)0.49248 (17)0.19818 (15)0.0489 (6)
H320.94490.49550.25380.059*
C330.9609 (3)0.57258 (18)0.15078 (19)0.0585 (7)
H331.04140.62820.17610.070*
C340.9032 (3)0.57155 (19)0.06981 (18)0.0583 (7)
H340.94720.62460.04030.070*
C350.7779 (3)0.49103 (18)0.03032 (14)0.0465 (6)
C360.6976 (3)0.4798 (2)0.05085 (16)0.0583 (7)
H360.73090.52870.08620.070*
C370.5730 (3)0.3995 (2)0.07831 (15)0.0603 (7)
H370.52400.39420.13270.072*
C380.5143 (3)0.3235 (2)0.02790 (14)0.0522 (6)
H380.42620.27000.04760.063*
C390.5908 (3)0.33051 (17)0.05099 (12)0.0403 (5)
C400.7222 (2)0.41218 (16)0.07868 (13)0.0381 (5)
C410.5557 (3)0.27367 (17)0.12338 (13)0.0391 (5)
C420.5437 (3)0.37730 (16)0.30692 (13)0.0395 (5)
C430.4711 (3)0.43741 (19)0.25804 (14)0.0521 (6)
H430.49990.44090.20280.062*
C440.3572 (3)0.4921 (2)0.28967 (15)0.0557 (6)
H440.31070.53260.25630.067*
C450.3133 (3)0.48635 (19)0.37064 (14)0.0518 (6)
C460.3809 (3)0.42677 (19)0.41970 (14)0.0526 (6)
H460.34950.42270.47440.063*
C470.4956 (3)0.37255 (18)0.38851 (13)0.0468 (6)
H470.54120.33230.42250.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0915 (3)0.1514 (3)0.05390 (18)0.0842 (2)0.00073 (15)0.01430 (18)
O10.0969 (15)0.1157 (16)0.0604 (12)0.0642 (13)0.0364 (10)0.0481 (11)
O20.0416 (9)0.0476 (9)0.0523 (9)0.0028 (8)0.0088 (7)0.0040 (7)
O30.0396 (9)0.0632 (11)0.0616 (10)0.0055 (8)0.0040 (8)0.0183 (9)
N10.0533 (11)0.0609 (12)0.0302 (9)0.0304 (10)0.0087 (8)0.0161 (8)
C10.0566 (15)0.0559 (14)0.0440 (13)0.0241 (12)0.0071 (11)0.0147 (11)
C20.0626 (16)0.0621 (16)0.0468 (14)0.0263 (13)0.0148 (12)0.0198 (12)
C30.0563 (15)0.0495 (14)0.0478 (13)0.0226 (12)0.0117 (11)0.0162 (11)
C40.0752 (18)0.0665 (17)0.0508 (14)0.0324 (14)0.0112 (13)0.0183 (13)
C50.080 (2)0.080 (2)0.0722 (19)0.0447 (16)0.0110 (15)0.0236 (16)
C60.090 (2)0.091 (2)0.081 (2)0.0588 (18)0.0273 (17)0.0196 (17)
C70.096 (2)0.096 (2)0.0582 (17)0.0569 (19)0.0241 (16)0.0151 (16)
C80.0745 (18)0.0646 (16)0.0513 (15)0.0318 (14)0.0119 (13)0.0119 (13)
C90.104 (2)0.114 (2)0.0448 (15)0.063 (2)0.0106 (15)0.0131 (16)
C100.0779 (19)0.088 (2)0.0482 (14)0.0444 (16)0.0145 (13)0.0246 (14)
C110.0591 (15)0.0617 (15)0.0477 (13)0.0267 (13)0.0123 (11)0.0216 (12)
C120.0500 (14)0.0508 (14)0.0411 (12)0.0211 (11)0.0058 (10)0.0117 (11)
C130.0416 (13)0.0516 (14)0.0523 (13)0.0169 (11)0.0066 (10)0.0118 (11)
C140.0432 (13)0.0448 (13)0.0451 (12)0.0107 (10)0.0042 (10)0.0115 (10)
C150.0436 (13)0.0444 (12)0.0303 (10)0.0145 (10)0.0000 (9)0.0067 (9)
C160.0442 (13)0.0684 (16)0.0517 (14)0.0223 (12)0.0117 (11)0.0240 (12)
C170.0568 (15)0.0588 (15)0.0535 (14)0.0218 (12)0.0141 (12)0.0287 (12)
C180.0408 (12)0.0436 (12)0.0334 (11)0.0142 (10)0.0002 (9)0.0092 (9)
C190.0339 (11)0.0373 (11)0.0311 (10)0.0089 (9)0.0039 (8)0.0086 (9)
C200.0387 (12)0.0416 (12)0.0299 (10)0.0131 (9)0.0048 (9)0.0102 (9)
C210.0543 (14)0.0582 (14)0.0314 (11)0.0267 (11)0.0043 (10)0.0110 (10)
C220.0412 (12)0.0438 (13)0.0432 (12)0.0088 (10)0.0059 (10)0.0134 (10)
C230.0477 (14)0.0438 (13)0.0514 (14)0.0044 (11)0.0003 (11)0.0010 (11)
C240.0454 (13)0.0430 (13)0.0388 (12)0.0139 (11)0.0004 (10)0.0076 (10)
C250.0597 (16)0.0545 (15)0.0502 (14)0.0137 (12)0.0052 (12)0.0008 (12)
C260.082 (2)0.0701 (18)0.0397 (13)0.0290 (16)0.0080 (13)0.0003 (12)
C270.0720 (18)0.0612 (16)0.0499 (14)0.0205 (15)0.0244 (13)0.0098 (13)
C280.0563 (15)0.0430 (13)0.0490 (13)0.0158 (11)0.0153 (11)0.0145 (11)
C290.0454 (13)0.0377 (12)0.0358 (11)0.0163 (10)0.0051 (9)0.0111 (9)
C300.0388 (12)0.0361 (12)0.0373 (11)0.0117 (10)0.0023 (9)0.0126 (9)
C310.0382 (12)0.0397 (12)0.0375 (11)0.0152 (10)0.0072 (9)0.0077 (9)
C320.0509 (14)0.0423 (13)0.0537 (14)0.0135 (11)0.0007 (11)0.0035 (11)
C330.0532 (15)0.0380 (14)0.084 (2)0.0088 (11)0.0119 (14)0.0063 (13)
C340.0606 (16)0.0446 (14)0.0810 (19)0.0212 (13)0.0266 (15)0.0267 (14)
C350.0511 (14)0.0504 (14)0.0496 (13)0.0267 (12)0.0180 (11)0.0202 (11)
C360.0695 (18)0.0729 (18)0.0512 (15)0.0384 (15)0.0252 (13)0.0333 (14)
C370.0707 (18)0.091 (2)0.0339 (12)0.0396 (16)0.0106 (12)0.0251 (13)
C380.0493 (14)0.0738 (17)0.0377 (12)0.0232 (12)0.0017 (10)0.0080 (12)
C390.0406 (13)0.0536 (14)0.0332 (11)0.0214 (11)0.0067 (9)0.0111 (10)
C400.0399 (12)0.0443 (12)0.0375 (11)0.0208 (10)0.0123 (9)0.0116 (10)
C410.0372 (12)0.0443 (13)0.0386 (11)0.0127 (11)0.0049 (9)0.0091 (10)
C420.0412 (12)0.0469 (13)0.0338 (11)0.0153 (10)0.0043 (9)0.0079 (10)
C430.0595 (15)0.0697 (16)0.0389 (12)0.0335 (13)0.0130 (11)0.0174 (11)
C440.0607 (16)0.0712 (17)0.0461 (13)0.0363 (13)0.0054 (11)0.0136 (12)
C450.0482 (14)0.0669 (16)0.0414 (13)0.0256 (12)0.0000 (10)0.0060 (11)
C460.0576 (15)0.0696 (16)0.0335 (12)0.0217 (13)0.0089 (11)0.0035 (11)
C470.0525 (14)0.0578 (14)0.0353 (12)0.0220 (12)0.0038 (10)0.0103 (10)
Geometric parameters (Å, º) top
Br1—C451.898 (2)C21—H21A0.9700
O1—C21.214 (3)C21—H21B0.9700
O2—C301.211 (2)C22—C231.519 (3)
O3—C411.204 (2)C22—H22A0.9700
N1—C421.386 (3)C22—H22B0.9700
N1—C201.446 (2)C23—C241.492 (3)
N1—C211.446 (3)C23—H23A0.9700
C1—C111.323 (3)C23—H23B0.9700
C1—C21.494 (3)C24—C291.382 (3)
C1—C101.505 (3)C24—C251.398 (3)
C2—C31.486 (3)C25—C261.373 (4)
C3—C41.373 (3)C25—H250.9300
C3—C81.392 (3)C26—C271.365 (4)
C4—C51.379 (4)C26—H260.9300
C4—H40.9300C27—C281.364 (3)
C5—C61.368 (4)C27—H270.9300
C5—H50.9300C28—C291.396 (3)
C6—C71.370 (4)C28—H280.9300
C6—H60.9300C29—C301.479 (3)
C7—C81.387 (4)C31—C321.352 (3)
C7—H70.9300C31—C401.403 (3)
C8—C91.506 (4)C32—C331.413 (3)
C9—C101.504 (4)C32—H320.9300
C9—H9A0.9700C33—C341.356 (4)
C9—H9B0.9700C33—H330.9300
C10—H10A0.9700C34—C351.402 (3)
C10—H10B0.9700C34—H340.9300
C11—C121.468 (3)C35—C361.408 (3)
C11—H110.9300C35—C401.408 (3)
C12—C171.378 (3)C36—C371.350 (4)
C12—C131.392 (3)C36—H360.9300
C13—C141.381 (3)C37—C381.408 (3)
C13—H130.9300C37—H370.9300
C14—C151.381 (3)C38—C391.369 (3)
C14—H140.9300C38—H380.9300
C15—C161.388 (3)C39—C401.397 (3)
C15—C181.516 (3)C39—C411.477 (3)
C16—C171.383 (3)C42—C471.389 (3)
C16—H160.9300C42—C431.389 (3)
C17—H170.9300C43—C441.380 (3)
C18—C211.509 (3)C43—H430.9300
C18—C191.563 (3)C44—C451.369 (3)
C18—H180.9800C44—H440.9300
C19—C221.533 (3)C45—C461.364 (3)
C19—C301.542 (3)C46—C471.379 (3)
C19—C201.602 (3)C46—H460.9300
C20—C311.518 (3)C47—H470.9300
C20—C411.568 (3)
C42—N1—C20124.33 (16)C23—C22—C19116.47 (17)
C42—N1—C21121.74 (16)C23—C22—H22A108.2
C20—N1—C21113.88 (16)C19—C22—H22A108.2
C11—C1—C2118.1 (2)C23—C22—H22B108.2
C11—C1—C10125.0 (2)C19—C22—H22B108.2
C2—C1—C10116.9 (2)H22A—C22—H22B107.3
O1—C2—C3120.3 (2)C24—C23—C22113.39 (18)
O1—C2—C1122.0 (2)C24—C23—H23A108.9
C3—C2—C1117.63 (19)C22—C23—H23A108.9
C4—C3—C8120.0 (2)C24—C23—H23B108.9
C4—C3—C2119.8 (2)C22—C23—H23B108.9
C8—C3—C2120.2 (2)H23A—C23—H23B107.7
C3—C4—C5121.2 (2)C29—C24—C25118.5 (2)
C3—C4—H4119.4C29—C24—C23120.92 (19)
C5—C4—H4119.4C25—C24—C23120.5 (2)
C6—C5—C4118.9 (3)C26—C25—C24120.4 (2)
C6—C5—H5120.6C26—C25—H25119.8
C4—C5—H5120.6C24—C25—H25119.8
C5—C6—C7120.7 (3)C27—C26—C25120.6 (2)
C5—C6—H6119.6C27—C26—H26119.7
C7—C6—H6119.6C25—C26—H26119.7
C6—C7—C8121.0 (3)C28—C27—C26120.0 (2)
C6—C7—H7119.5C28—C27—H27120.0
C8—C7—H7119.5C26—C27—H27120.0
C7—C8—C3118.2 (2)C27—C28—C29120.4 (2)
C7—C8—C9122.3 (2)C27—C28—H28119.8
C3—C8—C9119.5 (2)C29—C28—H28119.8
C10—C9—C8111.3 (2)C24—C29—C28119.9 (2)
C10—C9—H9A109.4C24—C29—C30122.51 (19)
C8—C9—H9A109.4C28—C29—C30117.6 (2)
C10—C9—H9B109.4O2—C30—C29120.32 (19)
C8—C9—H9B109.4O2—C30—C19119.93 (18)
H9A—C9—H9B108.0C29—C30—C19119.75 (18)
C9—C10—C1111.5 (2)C32—C31—C40118.9 (2)
C9—C10—H10A109.3C32—C31—C20132.80 (19)
C1—C10—H10A109.3C40—C31—C20108.34 (18)
C9—C10—H10B109.3C31—C32—C33118.7 (2)
C1—C10—H10B109.3C31—C32—H32120.7
H10A—C10—H10B108.0C33—C32—H32120.7
C1—C11—C12129.9 (2)C34—C33—C32122.6 (2)
C1—C11—H11115.1C34—C33—H33118.7
C12—C11—H11115.1C32—C33—H33118.7
C17—C12—C13117.2 (2)C33—C34—C35120.5 (2)
C17—C12—C11119.1 (2)C33—C34—H34119.8
C13—C12—C11123.5 (2)C35—C34—H34119.8
C14—C13—C12121.3 (2)C34—C35—C36128.4 (2)
C14—C13—H13119.4C34—C35—C40116.0 (2)
C12—C13—H13119.4C36—C35—C40115.6 (2)
C13—C14—C15121.4 (2)C37—C36—C35121.2 (2)
C13—C14—H14119.3C37—C36—H36119.4
C15—C14—H14119.3C35—C36—H36119.4
C14—C15—C16117.46 (19)C36—C37—C38122.6 (2)
C14—C15—C18120.05 (19)C36—C37—H37118.7
C16—C15—C18122.48 (19)C38—C37—H37118.7
C17—C16—C15121.0 (2)C39—C38—C37118.1 (2)
C17—C16—H16119.5C39—C38—H38121.0
C15—C16—H16119.5C37—C38—H38121.0
C12—C17—C16121.7 (2)C38—C39—C40119.4 (2)
C12—C17—H17119.1C38—C39—C41133.5 (2)
C16—C17—H17119.1C40—C39—C41106.76 (17)
C21—C18—C15116.01 (17)C39—C40—C31113.52 (18)
C21—C18—C19103.72 (16)C39—C40—C35123.1 (2)
C15—C18—C19115.92 (17)C31—C40—C35123.3 (2)
C21—C18—H18106.9O3—C41—C39127.9 (2)
C15—C18—H18106.9O3—C41—C20124.93 (18)
C19—C18—H18106.9C39—C41—C20107.03 (17)
C22—C19—C30110.14 (16)N1—C42—C47119.58 (18)
C22—C19—C18111.45 (16)N1—C42—C43122.77 (18)
C30—C19—C18109.23 (16)C47—C42—C43117.64 (19)
C22—C19—C20113.50 (16)C44—C43—C42121.4 (2)
C30—C19—C20112.50 (15)C44—C43—H43119.3
C18—C19—C2099.56 (15)C42—C43—H43119.3
N1—C20—C31115.98 (17)C45—C44—C43119.4 (2)
N1—C20—C41113.12 (16)C45—C44—H44120.3
C31—C20—C41101.41 (16)C43—C44—H44120.3
N1—C20—C19102.76 (14)C46—C45—C44120.4 (2)
C31—C20—C19113.35 (16)C46—C45—Br1119.69 (17)
C41—C20—C19110.53 (16)C44—C45—Br1119.87 (18)
N1—C21—C18103.74 (16)C45—C46—C47120.3 (2)
N1—C21—H21A111.0C45—C46—H46119.9
C18—C21—H21A111.0C47—C46—H46119.9
N1—C21—H21B111.0C46—C47—C42120.8 (2)
C18—C21—H21B111.0C46—C47—H47119.6
H21A—C21—H21B109.0C42—C47—H47119.6
C11—C1—C2—O13.7 (4)C23—C24—C25—C26178.9 (2)
C10—C1—C2—O1173.9 (3)C24—C25—C26—C271.6 (4)
C11—C1—C2—C3178.5 (2)C25—C26—C27—C281.4 (4)
C10—C1—C2—C33.9 (3)C26—C27—C28—C291.1 (4)
O1—C2—C3—C415.5 (4)C25—C24—C29—C283.1 (3)
C1—C2—C3—C4162.3 (2)C23—C24—C29—C28176.5 (2)
O1—C2—C3—C8165.4 (3)C25—C24—C29—C30176.65 (19)
C1—C2—C3—C816.8 (4)C23—C24—C29—C303.8 (3)
C8—C3—C4—C50.2 (4)C27—C28—C29—C243.4 (3)
C2—C3—C4—C5178.9 (2)C27—C28—C29—C30176.4 (2)
C3—C4—C5—C61.3 (4)C24—C29—C30—O2176.99 (19)
C4—C5—C6—C71.0 (5)C28—C29—C30—O22.8 (3)
C5—C6—C7—C80.4 (5)C24—C29—C30—C193.4 (3)
C6—C7—C8—C31.6 (5)C28—C29—C30—C19176.87 (17)
C6—C7—C8—C9179.1 (3)C22—C19—C30—O2159.31 (18)
C4—C3—C8—C71.3 (4)C18—C19—C30—O236.6 (2)
C2—C3—C8—C7179.6 (3)C20—C19—C30—O273.0 (2)
C4—C3—C8—C9179.4 (3)C22—C19—C30—C2920.3 (2)
C2—C3—C8—C90.3 (4)C18—C19—C30—C29143.05 (17)
C7—C8—C9—C10144.1 (3)C20—C19—C30—C29107.37 (19)
C3—C8—C9—C1036.7 (4)N1—C20—C31—C3242.7 (3)
C8—C9—C10—C155.0 (4)C41—C20—C31—C32165.7 (2)
C11—C1—C10—C9143.1 (3)C19—C20—C31—C3275.8 (3)
C2—C1—C10—C939.5 (3)N1—C20—C31—C40137.41 (18)
C2—C1—C11—C12171.6 (2)C41—C20—C31—C4014.5 (2)
C10—C1—C11—C125.7 (5)C19—C20—C31—C40104.02 (18)
C1—C11—C12—C17151.9 (3)C40—C31—C32—C333.1 (3)
C1—C11—C12—C1334.1 (4)C20—C31—C32—C33176.7 (2)
C17—C12—C13—C140.0 (3)C31—C32—C33—C340.4 (4)
C11—C12—C13—C14174.1 (2)C32—C33—C34—C352.3 (4)
C12—C13—C14—C150.6 (3)C33—C34—C35—C36176.4 (2)
C13—C14—C15—C160.8 (3)C33—C34—C35—C402.0 (3)
C13—C14—C15—C18179.3 (2)C34—C35—C36—C37176.8 (2)
C14—C15—C16—C170.3 (3)C40—C35—C36—C371.6 (3)
C18—C15—C16—C17178.8 (2)C35—C36—C37—C380.9 (4)
C13—C12—C17—C160.4 (4)C36—C37—C38—C392.0 (4)
C11—C12—C17—C16174.8 (2)C37—C38—C39—C400.3 (3)
C15—C16—C17—C120.3 (4)C37—C38—C39—C41172.9 (2)
C14—C15—C18—C21153.2 (2)C38—C39—C40—C31178.84 (19)
C16—C15—C18—C2125.2 (3)C41—C39—C40—C314.5 (2)
C14—C15—C18—C1984.7 (2)C38—C39—C40—C352.3 (3)
C16—C15—C18—C1996.8 (2)C41—C39—C40—C35172.05 (19)
C21—C18—C19—C2280.1 (2)C32—C31—C40—C39173.09 (19)
C15—C18—C19—C2248.2 (2)C20—C31—C40—C397.0 (2)
C21—C18—C19—C30157.96 (17)C32—C31—C40—C353.4 (3)
C15—C18—C19—C3073.7 (2)C20—C31—C40—C35176.43 (18)
C21—C18—C19—C2039.94 (19)C34—C35—C40—C39175.38 (19)
C15—C18—C19—C20168.29 (17)C36—C35—C40—C393.2 (3)
C42—N1—C20—C3165.1 (3)C34—C35—C40—C310.8 (3)
C21—N1—C20—C31112.3 (2)C36—C35—C40—C31179.42 (19)
C42—N1—C20—C4151.5 (3)C38—C39—C41—O310.8 (4)
C21—N1—C20—C41131.11 (19)C40—C39—C41—O3162.4 (2)
C42—N1—C20—C19170.68 (19)C38—C39—C41—C20173.1 (2)
C21—N1—C20—C1911.9 (2)C40—C39—C41—C2013.7 (2)
C22—C19—C20—N187.33 (19)N1—C20—C41—O334.4 (3)
C30—C19—C20—N1146.76 (17)C31—C20—C41—O3159.3 (2)
C18—C19—C20—N131.20 (19)C19—C20—C41—O380.2 (2)
C22—C19—C20—C31146.72 (17)N1—C20—C41—C39141.88 (17)
C30—C19—C20—C3120.8 (2)C31—C20—C41—C3917.0 (2)
C18—C19—C20—C3194.75 (18)C19—C20—C41—C39103.51 (18)
C22—C19—C20—C4133.6 (2)C20—N1—C42—C47172.7 (2)
C30—C19—C20—C4192.26 (19)C21—N1—C42—C4710.1 (3)
C18—C19—C20—C41152.18 (16)C20—N1—C42—C436.5 (3)
C42—N1—C21—C18163.82 (19)C21—N1—C42—C43170.7 (2)
C20—N1—C21—C1813.7 (2)N1—C42—C43—C44179.6 (2)
C15—C18—C21—N1162.26 (18)C47—C42—C43—C441.1 (4)
C19—C18—C21—N134.0 (2)C42—C43—C44—C450.7 (4)
C30—C19—C22—C2344.8 (2)C43—C44—C45—C460.2 (4)
C18—C19—C22—C23166.22 (18)C43—C44—C45—Br1179.39 (19)
C20—C19—C22—C2382.3 (2)C44—C45—C46—C470.7 (4)
C19—C22—C23—C2445.9 (3)Br1—C45—C46—C47178.94 (18)
C22—C23—C24—C2920.2 (3)C45—C46—C47—C420.2 (4)
C22—C23—C24—C25159.3 (2)N1—C42—C47—C46180.0 (2)
C29—C24—C25—C260.7 (3)C43—C42—C47—C460.7 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C3–C8 and C12–C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C22—H22B···O30.972.553.026 (3)111
C23—H23B···O30.972.403.113 (3)130
C17—H17···Cg1i0.932.983.720 (3)137
C26—H26···Cg2ii0.933.003.925 (3)178
Symmetry codes: (i) x1, y, z; (ii) x+2, y, z.

Experimental details

Crystal data
Chemical formulaC47H34BrNO3
Mr740.38
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)8.4178 (2), 13.2352 (3), 15.9610 (3)
α, β, γ (°)98.143 (1), 92.744 (2), 100.944 (1)
V3)1723.17 (7)
Z2
Radiation typeMo Kα
µ (mm1)1.24
Crystal size (mm)0.20 × 0.19 × 0.18
Data collection
DiffractometerBruker Kappa APEXII
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.719, 0.779
No. of measured, independent and
observed [I > 2σ(I)] reflections
30711, 6410, 4539
Rint0.034
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.098, 1.03
No. of reflections6410
No. of parameters469
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.53

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

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C3–C8 and C12–C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C22—H22B···O30.972.553.026 (3)111
C23—H23B···O30.972.403.113 (3)130
C17—H17···Cg1i0.932.983.720 (3)137
C26—H26···Cg2ii0.933.003.925 (3)178
Symmetry codes: (i) x1, y, z; (ii) x+2, y, z.
 

Acknowledgements

The authors acknowledge the IIT, Madras, for the data collection.

References

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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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