3,3′-{[(Biphenyl-2,2′-di­yl)bis­(methyl­ene)]bis­(­oxy)}bis­[N-(4-chloro­phen­yl)benzamide]

Rajadurai, R.; Padmanabhan, R.; Meenakshi Sundaram, S.S.; Ananthan, S.

doi:10.1107/S160053681301009X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o914-o915

doi:10.1107/S160053681301009X

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3,3′-{[(Biphenyl-2,2′-diyl)bis(methylene)]bis(oxy)}bis[N-(4-chlorophenyl)benzamide]

Raj Rajadurai,^a Ramar Padmanabhan,^b Soma Sundaram Meenakshi Sundaram ^a and Sarkkarai Ananthan ^c ^*

^aOrchid Chemicals and Pharmaceuticals Limited, R&D Centre, Chennai 600 119, India, ^bZydus Cadila, Vadodara, India, and ^cPresidency College, Chennai 600 005, India
^*Correspondence e-mail: sarkkaraiananthan@gmail.com

(Received 28 January 2013; accepted 12 April 2013; online 18 May 2013)

In the title compound, C₄₀H₃₀Cl₂N₂O₄, the two benzene rings of the biphenyl unit are twisted with respect to each other, making a dihedral angle of 73.07 (4)°. The benzene rings of the benzamide groups form dihedral angles of 77.09 (5) and 55.48 (6)° with the central biphenyl moiety. In the crystal, molecules are linked through N—H⋯O hydrogen bonds to form a fused R₂²(38) ring motif which forms a supermolecular ribbon network extending along the [100] plane. In the two 4-chlorophenyl rings, the five C atoms and their attached H atoms are disordered over two sets of sites, with site-occupancy factors of 0.657 (15):0.343 (15) and 0.509 (13):0.491 (13).

Related literature

For the pharmacological properties of benzo[c]phenanthridine derivatives, see: Clement et al. (2005 ); Stermitz et al. (1973 , 1975 ); Fang et al. (1993 ); Suzuki et al. (1992 ); Kanzawa et al. (1997 ); Guo et al. (2007 ); Nissanka et al. (2001 ); Lenfeld et al. (1981 ); Ishikawa (2001 ). For the synthesis of the starting material, see: Zhang et al. (2008 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₄₀H₃₀Cl₂N₂O₄
M_r = 673.56
Triclinic, $[P \overline 1]$
a = 9.4761 (2) Å
b = 11.9967 (3) Å
c = 15.9238 (4) Å
α = 75.944 (2)°
β = 86.163 (1)°
γ = 69.368 (3)°
V = 1643.07 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.890, T_max = 0.953
33102 measured reflections
6937 independent reflections
4799 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.101
S = 1.02
6937 reflections
551 parameters
268 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.91 (1)	2.02 (1)	2.8803 (16)	160 (2)
N1—H1⋯O4ⁱⁱ	0.90 (1)	2.05 (1)	2.9443 (16)	170 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681301009X/lx2280sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681301009X/lx2280Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681301009X/lx2280Isup3.cml

checkCIF report

Comment top

Benzo[c]phenanthridine derivatives are a class of substances possessing a wide range of pharmacological properties. Many naturally occurring alkaloids that contain a benzo[c]phennthridine ring system demonstrate interesting biological ativities as mentioned in the literature (Zhang et al., 2008; Clement et al., 2005). Antitumor activity (Stermitz et al., 1973, 1975; Fang et al., 1993; Suzuki et al., 1992; Kanzawa et al., 1997; Guo et al., 2007), antimicrobial activity (Nissanka et al., 2001), anti inflammatory activity (Lenfeld et al., 1981), antituberculosis activity (Ishikawa, 2001).

In the title molecule (Fig. 1), the two benzene rings of the biphenyl unit are twisted each other with a dihedral angle of 73.07 (4)°. The two phenyl rings (C8–C13 and C28–C32) of both the benzamide moiety form the dihedral angles of 77.09 (5)° and 55.48 (6)° with the central biphenyl moiety, respectively, In the two phenyl rings of the two 4–chlorophenyl groups, the five C atoms (C1/C2/C3/C5/C6) are disordered over two positions with site–occupancy factors, from refinement of 0.657 (15) (part A) and 0.343 (15) (part B), and the five C atoms (C36/C37/C38/C39/C40) are disordered over two positions with site–occupancy factors, from refinement of 0.509 (13) (part A) and 0.491 (13) (part B), respectively. In the crystal structure (Fig. 2), molecules are connected by two N—H···O hydrogen bonds (Table 1) to form fused R22 (38) ring motif which from a supermolecular ribbon network extending along the [100] plane.

Related literature top

For the pharmacological properties of benzo[c]phenanthridine derivatives, see: Clement et al. (2005); Stermitz et al. (1973, 1975); Fang et al. (1993); Suzuki et al. (1992); Kanzawa et al. (1997); Guo et al. (2007); Nissanka et al. (2001); Lenfeld et al. (1981); Ishikawa (2001). For the synthesis of the starting material, see: Zhang et al. (2008). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

To a solution of 3,3'-(biphenyl-2,2-diylbis(methylene))bis(oxy)dibenzoic acid (1.0 mmol) in dry DMF (10 ml), HBTU (2.5 mmol), diisopropylethyl amine (2.2 mmol) were added and stirred for 30 min. 4-Chloroaniline (3.0 mmol) was added to the reaction mixture and stirred for furher 3 h. The progress of the reaction wa monitored by HPLC. The reaction mixture was poured into ice water and filtered. The solid was washed with water folled by cold ethanol and dried under vaccum. The crude product was purified by column chromatography (SiO₂).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: 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. In the two phenyl rings of the two 4-chlorophenyl groups, the C1/C2/C3/C5/C6 atoms are disordered over two positions with site-occupancy factors, from refinement of 0.657 (15) (part A) and 0.343 (15) (part B), and the C36/C37/C38/C39/C40 atoms are disordered over two positions with site–occupancy factors, from refinement of 0.509 (13) (part A) and 0.491 (13) (part B), respectively.

Fig. 2. A view of N—H···O hydrogen bond interactions (dotted lines) in the crystal structure of the title compound. H atoms non–participating in hydrogen–bonding and disordered part B and D atoms were omitted for clarity. [Symmetry code: (i) - x, - y + 1, - z + 1; (ii) - x + 1, - y + 1, - z + 1.]

3,3'-{[(Biphenyl-2,2'-diyl)bis(methylene)]bis(oxy)}bis[N-(4-chlorophenyl)benzamide] top

Crystal data top

C₄₀H₃₀Cl₂N₂O₄	Z = 2
M_r = 673.56	F(000) = 700
Triclinic, P1	D_x = 1.361 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4761 (2) Å	Cell parameters from 8220 reflections
b = 11.9967 (3) Å	θ = 2.3–24.7°
c = 15.9238 (4) Å	µ = 0.24 mm⁻¹
α = 75.944 (2)°	T = 296 K
β = 86.163 (1)°	Block, colourless
γ = 69.368 (3)°	0.30 × 0.25 × 0.20 mm
V = 1643.07 (7) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	6937 independent reflections
Radiation source: fine-focus sealed tube	4799 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω and ϕ scan	θ_max = 26.7°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.890, T_max = 0.953	k = −15→15
33102 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: difference Fourier map
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0393P)² + 0.3325P] where P = (F_o² + 2F_c²)/3
6937 reflections	(Δ/σ)_max = 0.001
551 parameters	Δρ_max = 0.16 e Å⁻³
268 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₄₀H₃₀Cl₂N₂O₄	γ = 69.368 (3)°
M_r = 673.56	V = 1643.07 (7) Å³
Triclinic, P1	Z = 2
a = 9.4761 (2) Å	Mo Kα radiation
b = 11.9967 (3) Å	µ = 0.24 mm⁻¹
c = 15.9238 (4) Å	T = 296 K
α = 75.944 (2)°	0.30 × 0.25 × 0.20 mm
β = 86.163 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	6937 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4799 reflections with I > 2σ(I)
T_min = 0.890, T_max = 0.953	R_int = 0.032
33102 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	268 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.16 e Å⁻³
6937 reflections	Δρ_min = −0.19 e Å⁻³
551 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	Occ. (<1)
C1A	0.4646 (8)	1.2020 (6)	0.0018 (4)	0.0597 (14)	0.666 (15)
C2A	0.5814 (11)	1.0932 (7)	0.0296 (6)	0.0580 (13)	0.666 (15)
H2A	0.6728	1.0771	0.0012	0.070*	0.666 (15)
C3A	0.5602 (7)	1.0088 (9)	0.1004 (7)	0.0507 (14)	0.666 (15)
H3A	0.6365	0.9333	0.1182	0.061*	0.666 (15)
C4A	0.42764 (16)	1.03464 (14)	0.14526 (10)	0.0473 (4)	0.666 (15)
C5A	0.3087 (7)	1.1403 (5)	0.1137 (6)	0.0565 (18)	0.666 (15)
H5A	0.2151	1.1541	0.1397	0.068*	0.666 (15)
C6A	0.3294 (8)	1.2254 (7)	0.0436 (5)	0.0673 (18)	0.666 (15)
H6A	0.2513	1.2994	0.0242	0.081*	0.666 (15)
Cl1A	0.4763 (3)	1.3093 (2)	−0.09101 (16)	0.0976 (9)	0.666 (15)
C1B	0.456 (2)	1.2258 (13)	0.0167 (10)	0.080 (5)	0.334 (15)
C2B	0.575 (2)	1.1172 (15)	0.0392 (14)	0.074 (5)	0.334 (15)
H2B	0.6632	1.1063	0.0081	0.088*	0.334 (15)
C3B	0.5650 (13)	1.0243 (18)	0.1071 (15)	0.063 (5)	0.334 (15)
H3B	0.6498	0.9556	0.1269	0.076*	0.334 (15)
C4B	0.42764 (16)	1.03464 (14)	0.14526 (10)	0.0473 (4)	0.334 (15)
C5B	0.3174 (17)	1.1487 (9)	0.1283 (14)	0.062 (4)	0.334 (15)
H5B	0.2326	1.1613	0.1628	0.074*	0.334 (15)
C6B	0.3255 (19)	1.2451 (18)	0.0633 (11)	0.076 (4)	0.334 (15)
H6B	0.2466	1.3200	0.0514	0.091*	0.334 (15)
Cl1B	0.4951 (8)	1.3346 (11)	−0.0657 (11)	0.179 (3)	0.334 (15)
N1	0.40095 (14)	0.94586 (12)	0.21457 (9)	0.0492 (3)
O1	0.63544 (12)	0.85255 (11)	0.27605 (8)	0.0621 (3)
O2	0.17930 (12)	0.62038 (10)	0.34893 (7)	0.0500 (3)
C7	0.50297 (16)	0.86138 (14)	0.27347 (11)	0.0449 (4)
C8	0.44242 (15)	0.77927 (13)	0.33911 (10)	0.0411 (3)
C9	0.49327 (16)	0.74659 (14)	0.42458 (11)	0.0459 (4)
H9	0.5658	0.7742	0.4400	0.055*
C10	0.43533 (18)	0.67316 (15)	0.48594 (11)	0.0481 (4)
H10	0.4675	0.6529	0.5434	0.058*
C11	0.32978 (17)	0.62866 (14)	0.46393 (10)	0.0457 (4)
H11	0.2915	0.5789	0.5061	0.055*
C12	0.28221 (16)	0.65902 (13)	0.37867 (10)	0.0405 (3)
C13	0.33769 (16)	0.73458 (13)	0.31635 (10)	0.0415 (3)
H13	0.3047	0.7554	0.2591	0.050*
C14	0.13562 (18)	0.52786 (14)	0.40782 (10)	0.0466 (4)
H14A	0.0823	0.5596	0.4559	0.056*
H14B	0.2243	0.4577	0.4307	0.056*
C15	0.03557 (16)	0.49016 (13)	0.36031 (9)	0.0401 (3)
C16	−0.11978 (17)	0.54367 (14)	0.36437 (10)	0.0458 (4)
H16	−0.1597	0.6033	0.3959	0.055*
C17	−0.21617 (17)	0.51056 (15)	0.32282 (11)	0.0504 (4)
H17	−0.3200	0.5477	0.3262	0.061*
C18	−0.15817 (18)	0.42247 (16)	0.27652 (12)	0.0532 (4)
H18	−0.2225	0.3988	0.2489	0.064*
C19	−0.00360 (17)	0.36890 (15)	0.27094 (11)	0.0495 (4)
H19	0.0349	0.3097	0.2389	0.059*
C20	0.09528 (16)	0.40154 (13)	0.31206 (10)	0.0405 (3)
C21	0.26020 (16)	0.34897 (14)	0.29640 (10)	0.0420 (4)
C22	0.32557 (18)	0.42457 (16)	0.24000 (12)	0.0558 (4)
H22	0.2687	0.5068	0.2191	0.067*
C23	0.47267 (19)	0.38018 (19)	0.21453 (13)	0.0675 (5)
H23	0.5134	0.4317	0.1757	0.081*
C24	0.55876 (19)	0.25992 (19)	0.24657 (13)	0.0667 (5)
H24	0.6580	0.2294	0.2294	0.080*
C25	0.49781 (18)	0.18469 (17)	0.30407 (12)	0.0563 (4)
H25	0.5578	0.1037	0.3268	0.068*
C26	0.34869 (17)	0.22633 (14)	0.32927 (10)	0.0432 (4)
C27	0.28819 (19)	0.13376 (15)	0.38488 (10)	0.0487 (4)
H27A	0.2044	0.1309	0.3547	0.058*
H27B	0.3662	0.0534	0.3948	0.058*
C28	0.19174 (16)	0.07798 (13)	0.52451 (10)	0.0414 (3)
C29	0.19905 (17)	−0.03385 (14)	0.51121 (11)	0.0480 (4)
H29	0.2378	−0.0565	0.4602	0.058*
C30	0.14826 (18)	−0.11133 (15)	0.57439 (12)	0.0525 (4)
H30	0.1539	−0.1867	0.5657	0.063*
C31	0.08990 (17)	−0.07942 (14)	0.64945 (11)	0.0476 (4)
H31	0.0546	−0.1322	0.6908	0.057*
C32	0.08323 (15)	0.03173 (13)	0.66397 (10)	0.0406 (3)
C33	0.13408 (16)	0.11027 (14)	0.60071 (10)	0.0418 (3)
H33	0.1293	0.1853	0.6097	0.050*
C34	0.01855 (16)	0.06187 (14)	0.74681 (10)	0.0441 (4)
C35A	0.02175 (17)	0.18781 (16)	0.84834 (10)	0.0504 (4)	0.471 (11)
C36A	0.0729 (12)	0.2814 (7)	0.8494 (8)	0.0496 (17)	0.471 (11)
H36A	0.1397	0.2992	0.8074	0.059*	0.471 (11)
C37A	0.0283 (10)	0.3494 (9)	0.9108 (5)	0.0617 (19)	0.471 (11)
H37A	0.0694	0.4086	0.9127	0.074*	0.471 (11)
C38A	−0.0781 (10)	0.3285 (7)	0.9693 (5)	0.0662 (19)	0.471 (11)
C39A	−0.1328 (8)	0.2360 (8)	0.9690 (5)	0.0677 (18)	0.471 (11)
H39A	−0.2001	0.2187	1.0110	0.081*	0.471 (11)
C40A	−0.0877 (8)	0.1692 (8)	0.9063 (4)	0.0695 (19)	0.471 (11)
H40A	−0.1310	0.1118	0.9031	0.083*	0.471 (11)
Cl2A	−0.1473 (8)	0.4066 (5)	1.0500 (4)	0.1195 (14)	0.471 (11)
C35B	0.02175 (17)	0.18781 (16)	0.84834 (10)	0.0504 (4)	0.529 (11)
C36B	0.0312 (12)	0.2991 (6)	0.8493 (7)	0.066 (3)	0.529 (11)
H36B	0.0726	0.3399	0.8027	0.079*	0.529 (11)
C37B	−0.0201 (11)	0.3507 (8)	0.9187 (5)	0.071 (2)	0.529 (11)
H37B	−0.0200	0.4285	0.9176	0.085*	0.529 (11)
C38B	−0.0716 (8)	0.2859 (8)	0.9897 (4)	0.0669 (19)	0.529 (11)
C39B	−0.0711 (9)	0.1694 (9)	0.9937 (4)	0.0815 (19)	0.529 (11)
H39B	−0.1017	0.1248	1.0432	0.098*	0.529 (11)
C40B	−0.0239 (9)	0.1210 (6)	0.9220 (2)	0.0703 (16)	0.529 (11)
H40B	−0.0228	0.0429	0.9231	0.084*	0.529 (11)
Cl2B	−0.1290 (5)	0.3534 (9)	1.0766 (3)	0.1340 (18)	0.529 (11)
N2	0.07391 (14)	0.13319 (13)	0.77786 (9)	0.0485 (3)
O3	0.23884 (13)	0.16234 (10)	0.46603 (7)	0.0513 (3)
O4	−0.07818 (12)	0.02208 (11)	0.78374 (8)	0.0576 (3)
H1	0.3037 (11)	0.9519 (14)	0.2221 (10)	0.052 (5)*
H2	0.1523 (15)	0.1504 (15)	0.7493 (10)	0.063 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.074 (3)	0.056 (2)	0.049 (2)	−0.031 (2)	0.0084 (18)	−0.004 (2)
C2A	0.059 (2)	0.066 (3)	0.056 (2)	−0.031 (2)	0.0106 (19)	−0.014 (2)
C3A	0.046 (2)	0.053 (2)	0.056 (3)	−0.0224 (19)	0.008 (2)	−0.010 (2)
C4A	0.0425 (8)	0.0504 (9)	0.0529 (10)	−0.0227 (7)	0.0020 (7)	−0.0097 (8)
C5A	0.043 (2)	0.062 (3)	0.056 (4)	−0.0161 (19)	0.0025 (19)	−0.003 (2)
C6A	0.071 (2)	0.055 (3)	0.060 (3)	−0.012 (2)	0.005 (2)	−0.001 (2)
Cl1A	0.1158 (14)	0.0887 (11)	0.0705 (11)	−0.0396 (10)	0.0182 (9)	0.0157 (8)
C1B	0.087 (6)	0.069 (6)	0.079 (7)	−0.035 (4)	−0.001 (5)	0.003 (5)
C2B	0.059 (5)	0.085 (7)	0.079 (8)	−0.041 (5)	0.019 (5)	−0.004 (5)
C3B	0.045 (4)	0.072 (7)	0.073 (7)	−0.029 (4)	−0.005 (4)	−0.002 (5)
C4B	0.0425 (8)	0.0504 (9)	0.0529 (10)	−0.0227 (7)	0.0020 (7)	−0.0097 (8)
C5B	0.069 (6)	0.059 (5)	0.057 (6)	−0.021 (4)	0.001 (4)	−0.016 (4)
C6B	0.076 (5)	0.067 (6)	0.074 (7)	−0.011 (4)	−0.007 (4)	−0.016 (5)
Cl1B	0.192 (4)	0.156 (4)	0.163 (6)	−0.104 (4)	−0.034 (4)	0.087 (4)
N1	0.0342 (7)	0.0530 (8)	0.0594 (9)	−0.0211 (6)	0.0044 (6)	−0.0032 (7)
O1	0.0378 (6)	0.0767 (9)	0.0713 (8)	−0.0284 (6)	0.0008 (5)	−0.0034 (7)
O2	0.0601 (7)	0.0526 (7)	0.0451 (6)	−0.0355 (6)	−0.0043 (5)	−0.0005 (5)
C7	0.0351 (8)	0.0478 (9)	0.0558 (10)	−0.0185 (7)	0.0075 (7)	−0.0146 (8)
C8	0.0329 (7)	0.0387 (8)	0.0513 (9)	−0.0116 (6)	0.0059 (6)	−0.0123 (7)
C9	0.0375 (8)	0.0451 (9)	0.0567 (10)	−0.0134 (7)	−0.0015 (7)	−0.0159 (8)
C10	0.0503 (9)	0.0474 (9)	0.0446 (9)	−0.0133 (8)	−0.0041 (7)	−0.0111 (7)
C11	0.0517 (9)	0.0412 (9)	0.0438 (9)	−0.0186 (7)	0.0028 (7)	−0.0057 (7)
C12	0.0404 (8)	0.0373 (8)	0.0453 (9)	−0.0156 (7)	0.0014 (7)	−0.0096 (7)
C13	0.0399 (8)	0.0428 (9)	0.0427 (9)	−0.0159 (7)	0.0028 (6)	−0.0100 (7)
C14	0.0551 (9)	0.0445 (9)	0.0432 (9)	−0.0262 (8)	0.0023 (7)	−0.0028 (7)
C15	0.0454 (8)	0.0376 (8)	0.0378 (8)	−0.0209 (7)	0.0026 (6)	−0.0005 (7)
C16	0.0480 (9)	0.0412 (9)	0.0455 (9)	−0.0160 (7)	0.0088 (7)	−0.0065 (7)
C17	0.0367 (8)	0.0512 (10)	0.0581 (10)	−0.0154 (7)	0.0037 (7)	−0.0040 (8)
C18	0.0429 (9)	0.0574 (11)	0.0647 (11)	−0.0241 (8)	−0.0018 (8)	−0.0132 (9)
C19	0.0451 (9)	0.0481 (9)	0.0608 (11)	−0.0192 (7)	0.0032 (8)	−0.0186 (8)
C20	0.0398 (8)	0.0382 (8)	0.0428 (8)	−0.0175 (7)	0.0018 (6)	−0.0027 (7)
C21	0.0373 (8)	0.0452 (9)	0.0460 (9)	−0.0183 (7)	0.0018 (6)	−0.0094 (7)
C22	0.0447 (9)	0.0520 (10)	0.0667 (12)	−0.0202 (8)	0.0037 (8)	−0.0024 (9)
C23	0.0473 (10)	0.0727 (13)	0.0778 (13)	−0.0291 (10)	0.0091 (9)	0.0014 (11)
C24	0.0367 (9)	0.0782 (14)	0.0801 (14)	−0.0196 (9)	0.0071 (9)	−0.0111 (11)
C25	0.0426 (9)	0.0555 (11)	0.0629 (11)	−0.0100 (8)	−0.0042 (8)	−0.0088 (9)
C26	0.0434 (8)	0.0478 (9)	0.0397 (8)	−0.0178 (7)	−0.0021 (7)	−0.0093 (7)
C27	0.0538 (9)	0.0469 (9)	0.0446 (9)	−0.0168 (8)	0.0038 (7)	−0.0109 (7)
C28	0.0392 (8)	0.0378 (8)	0.0447 (9)	−0.0134 (7)	−0.0010 (7)	−0.0044 (7)
C29	0.0498 (9)	0.0402 (9)	0.0524 (10)	−0.0128 (7)	0.0020 (7)	−0.0122 (8)
C30	0.0552 (10)	0.0368 (9)	0.0663 (12)	−0.0172 (8)	−0.0006 (8)	−0.0112 (8)
C31	0.0414 (8)	0.0424 (9)	0.0573 (10)	−0.0181 (7)	−0.0007 (7)	−0.0026 (8)
C32	0.0303 (7)	0.0422 (9)	0.0480 (9)	−0.0133 (6)	−0.0013 (6)	−0.0066 (7)
C33	0.0403 (8)	0.0380 (8)	0.0485 (9)	−0.0150 (7)	0.0024 (7)	−0.0111 (7)
C34	0.0314 (7)	0.0475 (9)	0.0501 (9)	−0.0147 (7)	0.0008 (7)	−0.0037 (7)
C35A	0.0398 (8)	0.0713 (12)	0.0436 (9)	−0.0242 (8)	0.0049 (7)	−0.0136 (8)
C36A	0.053 (4)	0.052 (3)	0.042 (3)	−0.018 (3)	0.001 (3)	−0.009 (3)
C37A	0.067 (5)	0.071 (4)	0.051 (3)	−0.031 (3)	0.004 (3)	−0.012 (3)
C38A	0.082 (4)	0.069 (4)	0.051 (4)	−0.032 (3)	0.010 (3)	−0.015 (3)
C39A	0.064 (3)	0.087 (4)	0.068 (4)	−0.039 (3)	0.033 (3)	−0.038 (3)
C40A	0.048 (3)	0.107 (4)	0.082 (3)	−0.049 (3)	0.033 (3)	−0.051 (3)
Cl2A	0.166 (3)	0.135 (3)	0.091 (2)	−0.068 (2)	0.039 (2)	−0.0722 (19)
C35B	0.0398 (8)	0.0713 (12)	0.0436 (9)	−0.0242 (8)	0.0049 (7)	−0.0136 (8)
C36B	0.081 (6)	0.058 (3)	0.043 (3)	−0.012 (3)	0.001 (3)	−0.003 (2)
C37B	0.077 (5)	0.077 (3)	0.058 (3)	−0.019 (3)	0.005 (3)	−0.026 (3)
C38B	0.060 (3)	0.101 (5)	0.048 (3)	−0.032 (4)	0.009 (2)	−0.029 (3)
C39B	0.080 (4)	0.123 (5)	0.058 (3)	−0.056 (4)	0.023 (3)	−0.025 (3)
C40B	0.062 (4)	0.105 (4)	0.063 (3)	−0.049 (3)	0.022 (2)	−0.032 (2)
Cl2B	0.1161 (14)	0.217 (5)	0.083 (2)	−0.043 (3)	0.0195 (15)	−0.090 (3)
N2	0.0418 (7)	0.0659 (9)	0.0470 (8)	−0.0310 (7)	0.0128 (6)	−0.0149 (7)
O3	0.0683 (7)	0.0463 (6)	0.0445 (6)	−0.0270 (6)	0.0114 (5)	−0.0121 (5)
O4	0.0440 (6)	0.0703 (8)	0.0654 (8)	−0.0330 (6)	0.0127 (5)	−0.0118 (6)

Geometric parameters (Å, º) top

C1A—C6A	1.373 (2)	C21—C22	1.392 (2)
C1A—C2A	1.375 (2)	C21—C26	1.399 (2)
C1A—Cl1A	1.735 (3)	C22—C23	1.377 (2)
C2A—C3A	1.376 (2)	C22—H22	0.9300
C2A—H2A	0.9300	C23—C24	1.370 (3)
C3A—C4A	1.378 (2)	C23—H23	0.9300
C3A—H3A	0.9300	C24—C25	1.372 (2)
C4A—C5A	1.3747 (19)	C24—H24	0.9300
C5A—C6A	1.3738 (19)	C25—C26	1.390 (2)
C5A—H5A	0.9300	C25—H25	0.9300
C6A—H6A	0.9300	C26—C27	1.500 (2)
C1B—C6B	1.373 (2)	C27—O3	1.4239 (18)
C1B—C2B	1.375 (2)	C27—H27A	0.9700
C1B—Cl1B	1.735 (3)	C27—H27B	0.9700
C2B—C3B	1.376 (2)	C28—O3	1.3767 (17)
C2B—H2B	0.9300	C28—C33	1.383 (2)
C3B—H3B	0.9300	C28—C29	1.386 (2)
C5B—C6B	1.373 (2)	C29—C30	1.380 (2)
C5B—H5B	0.9300	C29—H29	0.9300
C6B—H6B	0.9300	C30—C31	1.366 (2)
N1—C7	1.346 (2)	C30—H30	0.9300
N1—H1	0.901 (9)	C31—C32	1.387 (2)
O1—C7	1.2247 (17)	C31—H31	0.9300
O2—C12	1.3702 (17)	C32—C33	1.389 (2)
O2—C14	1.4314 (17)	C32—C34	1.488 (2)
C7—C8	1.487 (2)	C33—H33	0.9300
C8—C13	1.386 (2)	C34—O4	1.2303 (17)
C8—C9	1.391 (2)	C34—N2	1.345 (2)
C9—C10	1.372 (2)	C35A—C36A	1.374 (2)
C9—H9	0.9300	C35A—C40A	1.383 (2)
C10—C11	1.386 (2)	C35A—N2	1.410 (2)
C10—H10	0.9300	C36A—C37A	1.374 (2)
C11—C12	1.380 (2)	C36A—H36A	0.9300
C11—H11	0.9300	C37A—C38A	1.373 (2)
C12—C13	1.383 (2)	C37A—H37A	0.9300
C13—H13	0.9300	C38A—C39A	1.382 (2)
C14—C15	1.497 (2)	C38A—Cl2A	1.731 (3)
C14—H14A	0.9700	C39A—C40A	1.383 (2)
C14—H14B	0.9700	C39A—H39A	0.9300
C15—C16	1.387 (2)	C40A—H40A	0.9300
C15—C20	1.398 (2)	C36B—C37B	1.374 (2)
C16—C17	1.376 (2)	C36B—H36B	0.9300
C16—H16	0.9300	C37B—C38B	1.373 (2)
C17—C18	1.370 (2)	C37B—H37B	0.9300
C17—H17	0.9300	C38B—C39B	1.382 (2)
C18—C19	1.383 (2)	C38B—Cl2B	1.732 (3)
C18—H18	0.9300	C39B—C40B	1.383 (2)
C19—C20	1.388 (2)	C39B—H39B	0.9300
C19—H19	0.9300	C40B—H40B	0.9300
C20—C21	1.494 (2)	N2—H2	0.905 (9)

C6A—C1A—C2A	120.6 (5)	C26—C21—C20	123.74 (13)
C6A—C1A—Cl1A	117.3 (5)	C23—C22—C21	121.43 (16)
C2A—C1A—Cl1A	121.9 (5)	C23—C22—H22	119.3
C1A—C2A—C3A	118.6 (8)	C21—C22—H22	119.3
C1A—C2A—H2A	120.7	C24—C23—C22	119.83 (16)
C3A—C2A—H2A	120.7	C24—C23—H23	120.1
C2A—C3A—C4A	121.0 (8)	C22—C23—H23	120.1
C2A—C3A—H3A	119.5	C23—C24—C25	119.67 (16)
C4A—C3A—H3A	119.5	C23—C24—H24	120.2
C5A—C4A—C3A	119.6 (5)	C25—C24—H24	120.2
C6A—C5A—C4A	119.4 (6)	C24—C25—C26	121.69 (16)
C6A—C5A—H5A	120.3	C24—C25—H25	119.2
C4A—C5A—H5A	120.3	C26—C25—H25	119.2
C1A—C6A—C5A	120.4 (7)	C25—C26—C21	118.80 (14)
C1A—C6A—H6A	119.8	C25—C26—C27	117.51 (15)
C5A—C6A—H6A	119.8	C21—C26—C27	123.49 (14)
C6B—C1B—C2B	120.4 (12)	O3—C27—C26	111.81 (13)
C6B—C1B—Cl1B	125.4 (11)	O3—C27—H27A	109.3
C2B—C1B—Cl1B	113.8 (11)	C26—C27—H27A	109.3
C1B—C2B—C3B	121.1 (16)	O3—C27—H27B	109.3
C1B—C2B—H2B	119.5	C26—C27—H27B	109.3
C3B—C2B—H2B	119.5	H27A—C27—H27B	107.9
C2B—C3B—H3B	120.5	O3—C28—C33	116.01 (13)
C6B—C5B—H5B	118.2	O3—C28—C29	124.31 (14)
C1B—C6B—C5B	116.9 (16)	C33—C28—C29	119.68 (14)
C1B—C6B—H6B	121.5	C30—C29—C28	119.35 (15)
C5B—C6B—H6B	121.5	C30—C29—H29	120.3
C7—N1—H1	117.6 (10)	C28—C29—H29	120.3
C12—O2—C14	117.22 (11)	C31—C30—C29	121.23 (15)
O1—C7—N1	124.04 (14)	C31—C30—H30	119.4
O1—C7—C8	121.00 (15)	C29—C30—H30	119.4
N1—C7—C8	114.94 (12)	C30—C31—C32	120.03 (14)
C13—C8—C9	119.87 (14)	C30—C31—H31	120.0
C13—C8—C7	121.17 (14)	C32—C31—H31	120.0
C9—C8—C7	118.96 (13)	C31—C32—C33	119.10 (15)
C10—C9—C8	119.32 (14)	C31—C32—C34	117.79 (13)
C10—C9—H9	120.3	C33—C32—C34	123.10 (14)
C8—C9—H9	120.3	C28—C33—C32	120.60 (14)
C9—C10—C11	121.23 (15)	C28—C33—H33	119.7
C9—C10—H10	119.4	C32—C33—H33	119.7
C11—C10—H10	119.4	O4—C34—N2	123.28 (15)
C12—C11—C10	119.25 (14)	O4—C34—C32	121.08 (14)
C12—C11—H11	120.4	N2—C34—C32	115.63 (12)
C10—C11—H11	120.4	C36A—C35A—C40A	118.5 (5)
O2—C12—C11	124.68 (13)	C36A—C35A—N2	113.6 (4)
O2—C12—C13	115.13 (13)	C40A—C35A—N2	127.2 (2)
C11—C12—C13	120.18 (14)	C37A—C36A—C35A	122.0 (8)
C12—C13—C8	120.12 (14)	C37A—C36A—H36A	119.0
C12—C13—H13	119.9	C35A—C36A—H36A	119.0
C8—C13—H13	119.9	C38A—C37A—C36A	118.9 (9)
O2—C14—C15	108.62 (12)	C38A—C37A—H37A	120.5
O2—C14—H14A	110.0	C36A—C37A—H37A	120.5
C15—C14—H14A	110.0	C37A—C38A—C39A	120.2 (6)
O2—C14—H14B	110.0	C37A—C38A—Cl2A	124.7 (6)
C15—C14—H14B	110.0	C39A—C38A—Cl2A	115.0 (5)
H14A—C14—H14B	108.3	C38A—C39A—C40A	120.0 (5)
C16—C15—C20	119.12 (14)	C38A—C39A—H39A	120.0
C16—C15—C14	119.48 (14)	C40A—C39A—H39A	120.0
C20—C15—C14	121.40 (13)	C39A—C40A—C35A	120.0 (4)
C17—C16—C15	121.51 (15)	C39A—C40A—H40A	120.0
C17—C16—H16	119.2	C35A—C40A—H40A	120.0
C15—C16—H16	119.2	C37B—C36B—H36B	119.8
C18—C17—C16	119.57 (15)	C38B—C37B—C36B	119.2 (8)
C18—C17—H17	120.2	C38B—C37B—H37B	120.4
C16—C17—H17	120.2	C36B—C37B—H37B	120.4
C17—C18—C19	119.81 (15)	C37B—C38B—C39B	121.8 (5)
C17—C18—H18	120.1	C37B—C38B—Cl2B	117.1 (5)
C19—C18—H18	120.1	C39B—C38B—Cl2B	121.0 (4)
C18—C19—C20	121.42 (15)	C38B—C39B—C40B	118.0 (4)
C18—C19—H19	119.3	C38B—C39B—H39B	121.0
C20—C19—H19	119.3	C40B—C39B—H39B	121.0
C19—C20—C15	118.57 (13)	C39B—C40B—H40B	119.6
C19—C20—C21	118.54 (14)	C34—N2—C35A	127.85 (13)
C15—C20—C21	122.66 (13)	C34—N2—H2	116.5 (11)
C22—C21—C26	118.54 (14)	C35A—N2—H2	115.6 (11)
C22—C21—C20	117.49 (14)	C28—O3—C27	116.35 (12)

C6A—C1A—C2A—C3A	−0.4 (16)	C20—C21—C22—C23	−172.93 (17)
Cl1A—C1A—C2A—C3A	−175.5 (9)	C21—C22—C23—C24	−1.6 (3)
C1A—C2A—C3A—C4A	−3.1 (18)	C22—C23—C24—C25	−0.2 (3)
C2A—C3A—C4A—C5A	7.1 (16)	C23—C24—C25—C26	1.8 (3)
C3A—C4A—C5A—C6A	−7.5 (13)	C24—C25—C26—C21	−1.5 (3)
C2A—C1A—C6A—C5A	−0.1 (15)	C24—C25—C26—C27	173.61 (16)
Cl1A—C1A—C6A—C5A	175.2 (8)	C22—C21—C26—C25	−0.3 (2)
C4A—C5A—C6A—C1A	4.1 (14)	C20—C21—C26—C25	174.13 (15)
C6B—C1B—C2B—C3B	2 (3)	C22—C21—C26—C27	−175.11 (15)
Cl1B—C1B—C2B—C3B	176 (2)	C20—C21—C26—C27	−0.7 (2)
C2B—C1B—C6B—C5B	−4 (3)	C25—C26—C27—O3	119.95 (16)
Cl1B—C1B—C6B—C5B	−177.7 (18)	C21—C26—C27—O3	−65.20 (19)
O1—C7—C8—C13	−141.98 (16)	O3—C28—C29—C30	−179.90 (14)
N1—C7—C8—C13	39.9 (2)	C33—C28—C29—C30	0.1 (2)
O1—C7—C8—C9	37.6 (2)	C28—C29—C30—C31	0.5 (2)
N1—C7—C8—C9	−140.53 (15)	C29—C30—C31—C32	−1.1 (2)
C13—C8—C9—C10	−2.0 (2)	C30—C31—C32—C33	1.1 (2)
C7—C8—C9—C10	178.49 (14)	C30—C31—C32—C34	179.99 (14)
C8—C9—C10—C11	1.5 (2)	O3—C28—C33—C32	179.91 (13)
C9—C10—C11—C12	−0.1 (2)	C29—C28—C33—C32	−0.1 (2)
C14—O2—C12—C11	−9.8 (2)	C31—C32—C33—C28	−0.5 (2)
C14—O2—C12—C13	170.86 (13)	C34—C32—C33—C28	−179.32 (13)
C10—C11—C12—O2	179.68 (14)	C31—C32—C34—O4	−29.4 (2)
C10—C11—C12—C13	−1.0 (2)	C33—C32—C34—O4	149.42 (15)
O2—C12—C13—C8	179.96 (13)	C31—C32—C34—N2	149.94 (14)
C11—C12—C13—C8	0.6 (2)	C33—C32—C34—N2	−31.2 (2)
C9—C8—C13—C12	0.9 (2)	C40A—C35A—C36A—C37A	5.7 (13)
C7—C8—C13—C12	−179.55 (14)	N2—C35A—C36A—C37A	176.8 (8)
C12—O2—C14—C15	−174.41 (13)	C35A—C36A—C37A—C38A	−4.3 (15)
O2—C14—C15—C16	−95.68 (16)	C36A—C37A—C38A—C39A	3.4 (13)
O2—C14—C15—C20	84.61 (17)	C36A—C37A—C38A—Cl2A	−179.5 (9)
C20—C15—C16—C17	0.7 (2)	C37A—C38A—C39A—C40A	−4.0 (12)
C14—C15—C16—C17	−179.01 (14)	Cl2A—C38A—C39A—C40A	178.6 (5)
C15—C16—C17—C18	0.2 (2)	C38A—C39A—C40A—C35A	5.5 (9)
C16—C17—C18—C19	−0.9 (2)	C36A—C35A—C40A—C39A	−6.2 (9)
C17—C18—C19—C20	0.6 (3)	N2—C35A—C40A—C39A	−176.0 (4)
C18—C19—C20—C15	0.3 (2)	C36B—C37B—C38B—C39B	1.0 (12)
C18—C19—C20—C21	−174.20 (15)	C36B—C37B—C38B—Cl2B	177.9 (7)
C16—C15—C20—C19	−1.0 (2)	C37B—C38B—C39B—C40B	−3.2 (9)
C14—C15—C20—C19	178.72 (13)	Cl2B—C38B—C39B—C40B	−180.0 (5)
C16—C15—C20—C21	173.33 (13)	O4—C34—N2—C35A	−9.0 (3)
C14—C15—C20—C21	−7.0 (2)	C32—C34—N2—C35A	171.68 (15)
C19—C20—C21—C22	102.90 (18)	C36A—C35A—N2—C34	−162.8 (6)
C15—C20—C21—C22	−71.4 (2)	C40A—C35A—N2—C34	7.4 (6)
C19—C20—C21—C26	−71.6 (2)	C33—C28—O3—C27	−175.62 (13)
C15—C20—C21—C26	114.09 (17)	C29—C28—O3—C27	4.4 (2)
C26—C21—C22—C23	1.9 (3)	C26—C27—O3—C28	−175.29 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.91 (1)	2.02 (1)	2.8803 (16)	160 (2)
N1—H1···O4ⁱⁱ	0.90 (1)	2.05 (1)	2.9443 (16)	170 (2)

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

Experimental details

Crystal data
Chemical formula	C₄₀H₃₀Cl₂N₂O₄
M_r	673.56
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.4761 (2), 11.9967 (3), 15.9238 (4)
α, β, γ (°)	75.944 (2), 86.163 (1), 69.368 (3)
V (Å³)	1643.07 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.890, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	33102, 6937, 4799
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.101, 1.02
No. of reflections	6937
No. of parameters	551
No. of restraints	268
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.905 (9)	2.015 (11)	2.8803 (16)	159.7 (16)
N1—H1···O4ⁱⁱ	0.901 (9)	2.053 (10)	2.9443 (16)	170.0 (15)

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

Acknowledgements

The authors are grateful to the X-ray Facility, IIT Madras, India, for data collection. Further thanks are due to R. Jagan of IITM, V. Silambarasan and Dr D. Velmurugan of Madras University. RR thanks Orchid Chemicals and Pharmaceuticals Ltd, for providing the laboratory and analytical facility.

References

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Volume 69| Part 6| June 2013| Pages o914-o915

doi:10.1107/S160053681301009X

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

3,3′-{[(Bi­phenyl-2,2′-di­yl)bis­­(methyl­ene)]bis­­(­­oxy)}bis­­[N-(4-chloro­phen­yl)benzamide]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,3′-{[(Biphenyl-2,2′-diyl)bis(methylene)]bis(oxy)}bis[N-(4-chlorophenyl)benzamide]