(2E)-2-Benzyl­idene-9-phenyl-3,4-di­hydro­acridin-1(2H)-one

Vinuchakkaravarthy, T.; Sankaran, M.; Mohan, P.S.; Velmurugan, D.

doi:10.1107/S1600536814015943

organic compounds

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ISSN: 2056-9890

Volume 70| Part 8| August 2014| Page o870

doi:10.1107/S1600536814015943

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(2E)-2-Benzylidene-9-phenyl-3,4-dihydroacridin-1(2H)-one

T. Vinuchakkaravarthy,^a M. Sankaran,^b P. S. Mohan ^b and D. Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Maraimalai (Guindy) Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, India
^*Correspondence e-mail: shirai2011@gmail.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 3 January 2014; accepted 8 July 2014; online 17 July 2014)

In the title compound, C₂₆H₁₉NO, the plane of the aromatic heterocycle makes a dihedral angle of 75.22 (4)° with that of the attached phenyl ring. In the crystal, molecules are connected by C—H⋯O interactions, generating R₂²(12) dimers. These dimers are further connected by C—H⋯π interactions, linking the molecules into chains running along the a-axis direction.

Keywords: crystal structure.

CCDC reference: 1012814

Related literature

For background to acridines, see: Kumar et al. (2012 ). For the biological activity of acridine derivatives, see: Pigatto et al. (2011 ); Das et al. (2011 ); Kumar et al. (2012); Prommier et al. (2006 ) Denny et al. (1982 ); Baguley & Ferguson (1998 ). For the synthesis of acridines, see: Tomar et al. (2010 ). For related structures, see: Buckleton & Waters (1984 ); Chantrapromma et al. (2010 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₆H₁₉NO
M_r = 361.42
Monoclinic, P 2₁ /c
a = 9.2222 (3) Å
b = 10.7555 (4) Å
c = 19.4962 (5) Å
β = 95.503 (2)°
V = 1924.90 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.662, T_max = 0.746
18382 measured reflections
4776 independent reflections
3205 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.131
S = 1.00
4776 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1ⁱ	0.97	2.58	3.2700 (18)	128
C26—H26⋯Cg1ⁱⁱ	0.93	2.71	3.577 (18)	156
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1012814

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814015943/bt6954sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015943/bt6954Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814015943/bt6954Isup3.cml

checkCIF report

Comment top

Acridine is structurally related to anthracene with one of the central CH group replaced by nitrogen. Amsacrine which is an acridine derivative is clinically used for the treatment of cancer (Denny et al., 1982; Baguley & Ferguson, 1998). The strong activity of acridine derivatives is due to their ability to intercalate into DNA base pairs and leading to cell cycle arrest and apoptosis (Prommier et al., 2006).

The phenyl (C21—C26) and benzyl (C14—C20) rings deviate from the plane of the acridine system by 72.48 (6) ° and 49.24 (6) °, respectively. The crystal packing is stabilized by intermolecular C—H···O (C10—H10B···O1) interactions generating a R²₂(12) ring motif (Bernstein et al., 1995). These dimers are further connected by C—H···π (C26—H26···Cg1) interactions generating chains running along the a-axis.

Related literature top

For background to acridines, see: Kumar et al. (2012). For the biological activity of acridine derivatives, see: Pigatto et al. (2011); Das et al. (2011); Kumar et al. (2012); Prommier et al. (2006) Denny et al. (1982); Baguley & Ferguson (1998). For the synthesis of acridines, see: Tomar et al. (2010). For related structures, see: Buckleton & Waters (1984); Chantrapromma et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A 1:2 molar mixture of 9-phenyl-3,4-dihydroacridin-1(2H)-one was treated with aromatic aldehydes in the presence of NaOH and allowed to stir at room temperature for 5–7 h. After completion of the reaction as inferred by the TLC, the mixture was poured into 200 g of crushed ice and neutralized with dil HCl. The precipitate thus formed after adding into crushed ice was filtered off and the residue subjected to column chromatography using petroleum ether: ethyl acetate mixture (3:1) v/v as eluent and compound obtained as a pale yellow solid.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. The cystal packing of the title compound showing the intermolecular C—H···O and C—H···π interactions chain running along aaxis, where Cg1 is the centroid of ring atoms C1—C6. Symmetry codes: (i) X,1/2-Y,1/2+Z; (ii) 1-X,-1/2+Y,1/2-Z; (iii) X,3/2-Y,1/2+Z and (iv) 1-X,1/2+Y,1/2-Z.

(2E)-2-Benzylidene-9-phenyl-3,4-dihydroacridin-1(2H)-one top

Crystal data top

C₂₆H₁₉NO	F(000) = 760
M_r = 361.42	D_x = 1.247 Mg m⁻³ D_m = 1.25 Mg m⁻³ D_m measured by not measured
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4776 reflections
a = 9.2222 (3) Å	θ = 2.1–28.3°
b = 10.7555 (4) Å	µ = 0.08 mm⁻¹
c = 19.4962 (5) Å	T = 293 K
β = 95.503 (2)°	Block, white
V = 1924.90 (11) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4776 independent reflections
Radiation source: fine-focus sealed tube	3205 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and ϕ scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→10
T_min = 0.662, T_max = 0.746	k = −13→14
18382 measured reflections	l = −25→25

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0587P)² + 0.3326P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.013
4776 reflections	Δρ_max = 0.23 e Å⁻³
254 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0041 (8)

Crystal data top

C₂₆H₁₉NO	V = 1924.90 (11) Å³
M_r = 361.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2222 (3) Å	µ = 0.08 mm⁻¹
b = 10.7555 (4) Å	T = 293 K
c = 19.4962 (5) Å	0.20 × 0.20 × 0.20 mm
β = 95.503 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4776 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3205 reflections with I > 2σ(I)
T_min = 0.662, T_max = 0.746	R_int = 0.029
18382 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.00	Δρ_max = 0.23 e Å⁻³
4776 reflections	Δρ_min = −0.16 e Å⁻³
254 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.47972 (17)	0.49247 (14)	0.17309 (8)	0.0542 (4)
H1	0.4841	0.4062	0.1757	0.065*
C2	0.5587 (2)	0.56214 (17)	0.22142 (9)	0.0711 (5)
H2	0.6162	0.5233	0.2569	0.085*
C3	0.5539 (2)	0.69204 (17)	0.21798 (10)	0.0811 (6)
H3	0.6089	0.7388	0.2511	0.097*
C4	0.4701 (2)	0.75058 (15)	0.16689 (9)	0.0677 (5)
H4	0.4674	0.8370	0.1655	0.081*
C5	0.38702 (16)	0.68116 (12)	0.11582 (7)	0.0457 (3)
C6	0.39092 (15)	0.54970 (12)	0.11883 (7)	0.0416 (3)
C7	0.30846 (14)	0.48187 (11)	0.06585 (6)	0.0376 (3)
C8	0.23412 (14)	0.54820 (11)	0.01290 (6)	0.0381 (3)
C9	0.23927 (14)	0.68112 (11)	0.01406 (7)	0.0399 (3)
C10	0.15959 (17)	0.75179 (12)	−0.04403 (7)	0.0484 (3)
H10A	0.1996	0.8350	−0.0456	0.058*
H10B	0.0577	0.7590	−0.0361	0.058*
C11	0.17193 (18)	0.68716 (12)	−0.11266 (7)	0.0502 (4)
H11A	0.1159	0.7328	−0.1490	0.060*
H11B	0.2730	0.6870	−0.1227	0.060*
C12	0.11714 (15)	0.55543 (12)	−0.11151 (7)	0.0434 (3)
C13	0.14319 (15)	0.48612 (11)	−0.04483 (6)	0.0399 (3)
C14	0.04150 (17)	0.49483 (12)	−0.16301 (7)	0.0475 (3)
H14	0.0134	0.4146	−0.1523	0.057*
C15	−0.00427 (18)	0.53472 (12)	−0.23384 (7)	0.0488 (3)
C16	0.0762 (2)	0.61459 (14)	−0.27197 (8)	0.0565 (4)
H16	0.1647	0.6460	−0.2525	0.068*
C17	0.0255 (2)	0.64745 (16)	−0.33848 (8)	0.0688 (5)
H17	0.0809	0.6998	−0.3635	0.083*
C18	−0.1053 (3)	0.60374 (18)	−0.36787 (9)	0.0773 (6)
H18	−0.1398	0.6280	−0.4122	0.093*
C19	−0.1857 (2)	0.52368 (18)	−0.33150 (9)	0.0739 (5)
H19	−0.2745	0.4935	−0.3515	0.089*
C20	−0.1349 (2)	0.48783 (15)	−0.26524 (8)	0.0601 (4)
H20	−0.1886	0.4319	−0.2415	0.072*
C21	0.31014 (14)	0.34287 (11)	0.06809 (6)	0.0398 (3)
C22	0.23121 (16)	0.27801 (12)	0.11307 (7)	0.0486 (3)
H22	0.1776	0.3208	0.1435	0.058*
C23	0.23196 (19)	0.14904 (14)	0.11288 (9)	0.0607 (4)
H23	0.1770	0.1056	0.1425	0.073*
C24	0.3134 (2)	0.08513 (14)	0.06919 (10)	0.0710 (5)
H24	0.3138	−0.0013	0.0691	0.085*
C25	0.3942 (2)	0.14968 (16)	0.02578 (10)	0.0766 (5)
H25	0.4509	0.1068	−0.0033	0.092*
C26	0.39204 (19)	0.27804 (14)	0.02481 (9)	0.0604 (4)
H26	0.4463	0.3209	−0.0053	0.072*
N1	0.31024 (13)	0.74545 (10)	0.06376 (6)	0.0459 (3)
O1	0.09155 (12)	0.38323 (8)	−0.03732 (5)	0.0517 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0594 (9)	0.0455 (8)	0.0552 (8)	0.0054 (7)	−0.0065 (7)	−0.0014 (6)
C2	0.0810 (12)	0.0635 (10)	0.0627 (10)	0.0080 (9)	−0.0252 (9)	−0.0038 (8)
C3	0.1013 (15)	0.0616 (11)	0.0722 (11)	0.0025 (10)	−0.0351 (11)	−0.0180 (9)
C4	0.0883 (13)	0.0435 (8)	0.0671 (10)	0.0003 (8)	−0.0153 (9)	−0.0135 (7)
C5	0.0519 (8)	0.0371 (7)	0.0476 (7)	0.0009 (6)	0.0017 (6)	−0.0063 (6)
C6	0.0442 (7)	0.0374 (7)	0.0431 (7)	0.0019 (6)	0.0029 (6)	−0.0019 (5)
C7	0.0401 (7)	0.0310 (6)	0.0421 (6)	0.0006 (5)	0.0059 (5)	0.0004 (5)
C8	0.0424 (7)	0.0301 (6)	0.0419 (7)	−0.0008 (5)	0.0045 (5)	0.0012 (5)
C9	0.0441 (7)	0.0298 (6)	0.0460 (7)	−0.0005 (5)	0.0054 (6)	0.0008 (5)
C10	0.0619 (9)	0.0281 (6)	0.0537 (8)	−0.0006 (6)	−0.0023 (7)	0.0052 (6)
C11	0.0655 (9)	0.0372 (7)	0.0470 (7)	−0.0054 (6)	0.0013 (7)	0.0077 (6)
C12	0.0527 (8)	0.0340 (6)	0.0434 (7)	0.0007 (6)	0.0039 (6)	0.0030 (5)
C13	0.0467 (7)	0.0299 (6)	0.0428 (7)	−0.0002 (5)	0.0028 (6)	0.0022 (5)
C14	0.0638 (9)	0.0346 (7)	0.0437 (7)	0.0006 (6)	0.0037 (6)	0.0023 (5)
C15	0.0669 (9)	0.0376 (7)	0.0415 (7)	0.0072 (7)	0.0042 (7)	−0.0024 (6)
C16	0.0744 (11)	0.0466 (8)	0.0493 (8)	0.0060 (7)	0.0093 (7)	0.0015 (7)
C17	0.1057 (15)	0.0537 (9)	0.0488 (9)	0.0118 (10)	0.0160 (10)	0.0080 (7)
C18	0.1155 (17)	0.0686 (12)	0.0457 (9)	0.0241 (11)	−0.0039 (10)	0.0050 (8)
C19	0.0860 (13)	0.0770 (12)	0.0544 (10)	0.0099 (10)	−0.0154 (9)	−0.0101 (9)
C20	0.0771 (11)	0.0542 (9)	0.0477 (8)	−0.0002 (8)	0.0000 (8)	−0.0060 (7)
C21	0.0437 (7)	0.0315 (6)	0.0429 (7)	0.0038 (5)	−0.0031 (6)	0.0013 (5)
C22	0.0569 (9)	0.0395 (7)	0.0485 (8)	0.0022 (6)	0.0000 (6)	0.0072 (6)
C23	0.0715 (11)	0.0423 (8)	0.0648 (10)	−0.0094 (7)	−0.0124 (8)	0.0168 (7)
C24	0.0966 (14)	0.0291 (7)	0.0817 (12)	0.0063 (8)	−0.0204 (11)	0.0012 (8)
C25	0.1012 (15)	0.0443 (9)	0.0846 (13)	0.0234 (9)	0.0111 (11)	−0.0074 (9)
C26	0.0708 (10)	0.0422 (8)	0.0705 (10)	0.0103 (7)	0.0191 (8)	0.0008 (7)
N1	0.0549 (7)	0.0322 (5)	0.0499 (6)	0.0004 (5)	0.0015 (5)	−0.0035 (5)
O1	0.0673 (7)	0.0343 (5)	0.0514 (6)	−0.0106 (4)	−0.0052 (5)	0.0058 (4)

Geometric parameters (Å, º) top

C1—C2	1.359 (2)	C13—O1	1.2191 (15)
C1—C6	1.4151 (19)	C14—C15	1.4689 (18)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.399 (2)	C15—C20	1.393 (2)
C2—H2	0.9300	C15—C16	1.395 (2)
C3—C4	1.356 (2)	C16—C17	1.381 (2)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.411 (2)	C17—C18	1.369 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—N1	1.3682 (17)	C18—C19	1.377 (3)
C5—C6	1.4154 (18)	C18—H18	0.9300
C6—C7	1.4236 (17)	C19—C20	1.386 (2)
C7—C8	1.3818 (17)	C19—H19	0.9300
C7—C21	1.4957 (17)	C20—H20	0.9300
C8—C9	1.4304 (17)	C21—C26	1.3750 (19)
C8—C13	1.4949 (17)	C21—C22	1.3813 (19)
C9—N1	1.3132 (16)	C22—C23	1.387 (2)
C9—C10	1.4970 (18)	C22—H22	0.9300
C10—C11	1.522 (2)	C23—C24	1.373 (3)
C10—H10A	0.9700	C23—H23	0.9300
C10—H10B	0.9700	C24—C25	1.369 (3)
C11—C12	1.5051 (18)	C24—H24	0.9300
C11—H11A	0.9700	C25—C26	1.381 (2)
C11—H11B	0.9700	C25—H25	0.9300
C12—C14	1.3361 (18)	C26—H26	0.9300
C12—C13	1.4978 (17)

C2—C1—C6	120.76 (14)	O1—C13—C12	121.60 (12)
C2—C1—H1	119.6	C8—C13—C12	117.57 (11)
C6—C1—H1	119.6	C12—C14—C15	130.26 (13)
C1—C2—C3	120.33 (15)	C12—C14—H14	114.9
C1—C2—H2	119.8	C15—C14—H14	114.9
C3—C2—H2	119.8	C20—C15—C16	118.07 (14)
C4—C3—C2	120.80 (15)	C20—C15—C14	117.78 (14)
C4—C3—H3	119.6	C16—C15—C14	124.14 (14)
C2—C3—H3	119.6	C17—C16—C15	120.55 (17)
C3—C4—C5	120.37 (15)	C17—C16—H16	119.7
C3—C4—H4	119.8	C15—C16—H16	119.7
C5—C4—H4	119.8	C18—C17—C16	120.70 (18)
N1—C5—C4	117.62 (13)	C18—C17—H17	119.7
N1—C5—C6	123.01 (12)	C16—C17—H17	119.7
C4—C5—C6	119.32 (13)	C17—C18—C19	119.74 (16)
C1—C6—C5	118.43 (12)	C17—C18—H18	120.1
C1—C6—C7	123.37 (12)	C19—C18—H18	120.1
C5—C6—C7	118.18 (12)	C18—C19—C20	120.23 (18)
C8—C7—C6	118.02 (11)	C18—C19—H19	119.9
C8—C7—C21	122.74 (11)	C20—C19—H19	119.9
C6—C7—C21	119.20 (11)	C19—C20—C15	120.66 (17)
C7—C8—C9	119.39 (11)	C19—C20—H20	119.7
C7—C8—C13	122.29 (11)	C15—C20—H20	119.7
C9—C8—C13	118.27 (11)	C26—C21—C22	119.17 (13)
N1—C9—C8	123.48 (12)	C26—C21—C7	119.59 (12)
N1—C9—C10	117.68 (11)	C22—C21—C7	121.24 (12)
C8—C9—C10	118.84 (11)	C21—C22—C23	120.02 (14)
C9—C10—C11	111.14 (11)	C21—C22—H22	120.0
C9—C10—H10A	109.4	C23—C22—H22	120.0
C11—C10—H10A	109.4	C24—C23—C22	120.35 (16)
C9—C10—H10B	109.4	C24—C23—H23	119.8
C11—C10—H10B	109.4	C22—C23—H23	119.8
H10A—C10—H10B	108.0	C25—C24—C23	119.48 (15)
C12—C11—C10	111.30 (11)	C25—C24—H24	120.3
C12—C11—H11A	109.4	C23—C24—H24	120.3
C10—C11—H11A	109.4	C24—C25—C26	120.52 (17)
C12—C11—H11B	109.4	C24—C25—H25	119.7
C10—C11—H11B	109.4	C26—C25—H25	119.7
H11A—C11—H11B	108.0	C21—C26—C25	120.43 (16)
C14—C12—C13	115.98 (12)	C21—C26—H26	119.8
C14—C12—C11	126.86 (12)	C25—C26—H26	119.8
C13—C12—C11	117.09 (11)	C9—N1—C5	117.84 (11)
O1—C13—C8	120.83 (11)

C6—C1—C2—C3	−0.3 (3)	C14—C12—C13—O1	−3.7 (2)
C1—C2—C3—C4	0.4 (3)	C11—C12—C13—O1	173.38 (13)
C2—C3—C4—C5	−0.5 (3)	C14—C12—C13—C8	176.83 (12)
C3—C4—C5—N1	−176.88 (17)	C11—C12—C13—C8	−6.04 (18)
C3—C4—C5—C6	0.6 (3)	C13—C12—C14—C15	179.30 (14)
C2—C1—C6—C5	0.4 (2)	C11—C12—C14—C15	2.5 (3)
C2—C1—C6—C7	178.48 (15)	C12—C14—C15—C20	−148.09 (16)
N1—C5—C6—C1	176.83 (13)	C12—C14—C15—C16	33.2 (2)
C4—C5—C6—C1	−0.5 (2)	C20—C15—C16—C17	1.1 (2)
N1—C5—C6—C7	−1.4 (2)	C14—C15—C16—C17	179.87 (14)
C4—C5—C6—C7	−178.70 (14)	C15—C16—C17—C18	0.9 (3)
C1—C6—C7—C8	−175.42 (13)	C16—C17—C18—C19	−1.6 (3)
C5—C6—C7—C8	2.67 (18)	C17—C18—C19—C20	0.3 (3)
C1—C6—C7—C21	2.24 (19)	C18—C19—C20—C15	1.8 (3)
C5—C6—C7—C21	−179.67 (12)	C16—C15—C20—C19	−2.5 (2)
C6—C7—C8—C9	−1.66 (18)	C14—C15—C20—C19	178.72 (14)
C21—C7—C8—C9	−179.24 (12)	C8—C7—C21—C26	74.02 (18)
C6—C7—C8—C13	−179.36 (11)	C6—C7—C21—C26	−103.53 (15)
C21—C7—C8—C13	3.06 (19)	C8—C7—C21—C22	−106.21 (15)
C7—C8—C9—N1	−0.88 (19)	C6—C7—C21—C22	76.24 (16)
C13—C8—C9—N1	176.92 (12)	C26—C21—C22—C23	−1.8 (2)
C7—C8—C9—C10	179.33 (12)	C7—C21—C22—C23	178.44 (13)
C13—C8—C9—C10	−2.87 (18)	C21—C22—C23—C24	1.4 (2)
N1—C9—C10—C11	141.67 (13)	C22—C23—C24—C25	0.0 (3)
C8—C9—C10—C11	−38.53 (17)	C23—C24—C25—C26	−1.2 (3)
C9—C10—C11—C12	56.53 (17)	C22—C21—C26—C25	0.7 (2)
C10—C11—C12—C14	142.07 (15)	C7—C21—C26—C25	−179.55 (15)
C10—C11—C12—C13	−34.70 (18)	C24—C25—C26—C21	0.8 (3)
C7—C8—C13—O1	24.48 (19)	C8—C9—N1—C5	2.25 (19)
C9—C8—C13—O1	−153.24 (13)	C10—C9—N1—C5	−177.96 (12)
C7—C8—C13—C12	−156.08 (12)	C4—C5—N1—C9	176.28 (13)
C9—C8—C13—C12	26.19 (17)	C6—C5—N1—C9	−1.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1ⁱ	0.97	2.58	3.2700 (18)	128
C26—H26···Cg1ⁱⁱ	0.93	2.71	3.577 (18)	156

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1ⁱ	0.97	2.58	3.2700 (18)	128
C26—H26···Cg1ⁱⁱ	0.93	2.71	3.577 (18)	156

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

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TV and DV also thank the UGC (SAP–CAS) for the facilities to the department.

References

Baguley, B. C. & Ferguson, L. R. (1998). Biochim. Biophys. Acta, 1400, 213–222. Web of Science CrossRef CAS PubMed Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Buckleton, J. S. & Waters, T. N. (1984). Acta Cryst. C40, 1587–1589. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Chantrapromma, S., Boonnak, N., Razak, I. A. & Fun, H.-K. (2010). Acta Cryst. E66, o81–o82. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Das, S., Kundu, S. & Suresh, K. G. (2011). DNA Cell Biol. 30, 525–535. Web of Science CrossRef CAS PubMed Google Scholar
Denny, W. A., Cain B. F., Atwell, G. J., Hansch, C. & Panthananickal, A. (1982). J. Med. Chem. 25, 276–315. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kumar, R., Kaur, M. & Kumari, M. (2012). Acta Pol. Pharm. 69, 3–9. Web of Science CAS PubMed Google Scholar
Pigatto, M. C., Lima, M. C. A., Galdino, S. L., Pitta, I. R., Vessecchi, R., Assis, M. D., Santos, J. S., Costa, T. C. T. D. & Lopes, P. N. (2011). Eur. J. Med. Chem. 1, 4245–4251. Web of Science CrossRef Google Scholar
Prommier, Y. & Goldwasser, F., Chabner, B. A. & Longo, D. L. (2006). Editors. Cancer Chemother. Biother. pp. 451–475. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tomar, V., Bhattacharjee, G., Uddin, K., Rajakumar, S., Srivastava, K. & Puri, S. K. (2010). Eur. J. Med. Chem. 45, 745–751. Web of Science CrossRef CAS PubMed Google Scholar