supplementary materials


lx2280 scheme

Acta Cryst. (2013). E69, o914-o915    [ doi:10.1107/S160053681301009X ]

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

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

Abstract top

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).

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).

Refinement top

The carbon hydrogen atoms were treated as riding atoms with a distance d(C—H) = 0.93 Å with Uiso (H) = -1.2Ueq(C) [for aromatic C—H] and d(C—H) = 0.97 Å with Uiso (H) = -1.2Ueq(C) [for CH2], respectively. The nitrogen attached H atoms identified from the difference electron density map were restrained to a distance of 0.92 (1) Å. In the molecular structure the two terminal 4–chloroaniline moieties are positionally disordered over two sites with refined occupancies set of 0.666 (15): 0.334 (15) and 0.529 (11): 0.471 (11), respectively. The positions of the atoms C4B and C35B were constrained to share the same site as that of C4A and C35A with equal atomic displacement parameters. The bond lengths of the disordered components were made similar using standard similarity restrains with suitable s.u. 0.002 Å. The ADP of the disordered compound were allowed to behave isotropically with s.u. of 0.01 followed by the appropriate rigid bond restrains.

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
[Figure 1] 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.
[Figure 2] 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
C40H30Cl2N2O4Z = 2
Mr = 673.56F(000) = 700
Triclinic, P1Dx = 1.361 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4761 (2) ÅCell parameters from 8220 reflections
b = 11.9967 (3) Åθ = 2.3–24.7°
c = 15.9238 (4) ŵ = 0.24 mm1
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 tube4799 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω and φ scanθmax = 26.7°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1111
Tmin = 0.890, Tmax = 0.953k = 1515
33102 measured reflectionsl = 2020
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)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0393P)2 + 0.3325P]
where P = (Fo2 + 2Fc2)/3
6937 reflections(Δ/σ)max = 0.001
551 parametersΔρmax = 0.16 e Å3
268 restraintsΔρmin = 0.19 e Å3
Crystal data top
C40H30Cl2N2O4γ = 69.368 (3)°
Mr = 673.56V = 1643.07 (7) Å3
Triclinic, P1Z = 2
a = 9.4761 (2) ÅMo Kα radiation
b = 11.9967 (3) ŵ = 0.24 mm1
c = 15.9238 (4) ÅT = 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)
Tmin = 0.890, Tmax = 0.953Rint = 0.032
33102 measured reflectionsθmax = 26.7°
Refinement top
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101Δρmax = 0.16 e Å3
S = 1.02Δρmin = 0.19 e Å3
6937 reflectionsAbsolute structure: ?
551 parametersFlack parameter: ?
268 restraintsRogers parameter: ?
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
xyzUiso*/UeqOcc. (<1)
C1A0.4646 (8)1.2020 (6)0.0018 (4)0.0597 (14)0.666 (15)
C2A0.5814 (11)1.0932 (7)0.0296 (6)0.0580 (13)0.666 (15)
H2A0.67281.07710.00120.070*0.666 (15)
C3A0.5602 (7)1.0088 (9)0.1004 (7)0.0507 (14)0.666 (15)
H3A0.63650.93330.11820.061*0.666 (15)
C4A0.42764 (16)1.03464 (14)0.14526 (10)0.0473 (4)0.666 (15)
C5A0.3087 (7)1.1403 (5)0.1137 (6)0.0565 (18)0.666 (15)
H5A0.21511.15410.13970.068*0.666 (15)
C6A0.3294 (8)1.2254 (7)0.0436 (5)0.0673 (18)0.666 (15)
H6A0.25131.29940.02420.081*0.666 (15)
Cl1A0.4763 (3)1.3093 (2)0.09101 (16)0.0976 (9)0.666 (15)
C1B0.456 (2)1.2258 (13)0.0167 (10)0.080 (5)0.334 (15)
C2B0.575 (2)1.1172 (15)0.0392 (14)0.074 (5)0.334 (15)
H2B0.66321.10630.00810.088*0.334 (15)
C3B0.5650 (13)1.0243 (18)0.1071 (15)0.063 (5)0.334 (15)
H3B0.64980.95560.12690.076*0.334 (15)
C4B0.42764 (16)1.03464 (14)0.14526 (10)0.0473 (4)0.334 (15)
C5B0.3174 (17)1.1487 (9)0.1283 (14)0.062 (4)0.334 (15)
H5B0.23261.16130.16280.074*0.334 (15)
C6B0.3255 (19)1.2451 (18)0.0633 (11)0.076 (4)0.334 (15)
H6B0.24661.32000.05140.091*0.334 (15)
Cl1B0.4951 (8)1.3346 (11)0.0657 (11)0.179 (3)0.334 (15)
N10.40095 (14)0.94586 (12)0.21457 (9)0.0492 (3)
O10.63544 (12)0.85255 (11)0.27605 (8)0.0621 (3)
O20.17930 (12)0.62038 (10)0.34893 (7)0.0500 (3)
C70.50297 (16)0.86138 (14)0.27347 (11)0.0449 (4)
C80.44242 (15)0.77927 (13)0.33911 (10)0.0411 (3)
C90.49327 (16)0.74659 (14)0.42458 (11)0.0459 (4)
H90.56580.77420.44000.055*
C100.43533 (18)0.67316 (15)0.48594 (11)0.0481 (4)
H100.46750.65290.54340.058*
C110.32978 (17)0.62866 (14)0.46393 (10)0.0457 (4)
H110.29150.57890.50610.055*
C120.28221 (16)0.65902 (13)0.37867 (10)0.0405 (3)
C130.33769 (16)0.73458 (13)0.31635 (10)0.0415 (3)
H130.30470.75540.25910.050*
C140.13562 (18)0.52786 (14)0.40782 (10)0.0466 (4)
H14A0.08230.55960.45590.056*
H14B0.22430.45770.43070.056*
C150.03557 (16)0.49016 (13)0.36031 (9)0.0401 (3)
C160.11978 (17)0.54367 (14)0.36437 (10)0.0458 (4)
H160.15970.60330.39590.055*
C170.21617 (17)0.51056 (15)0.32282 (11)0.0504 (4)
H170.32000.54770.32620.061*
C180.15817 (18)0.42247 (16)0.27652 (12)0.0532 (4)
H180.22250.39880.24890.064*
C190.00360 (17)0.36890 (15)0.27094 (11)0.0495 (4)
H190.03490.30970.23890.059*
C200.09528 (16)0.40154 (13)0.31206 (10)0.0405 (3)
C210.26020 (16)0.34897 (14)0.29640 (10)0.0420 (4)
C220.32557 (18)0.42457 (16)0.24000 (12)0.0558 (4)
H220.26870.50680.21910.067*
C230.47267 (19)0.38018 (19)0.21453 (13)0.0675 (5)
H230.51340.43170.17570.081*
C240.55876 (19)0.25992 (19)0.24657 (13)0.0667 (5)
H240.65800.22940.22940.080*
C250.49781 (18)0.18469 (17)0.30407 (12)0.0563 (4)
H250.55780.10370.32680.068*
C260.34869 (17)0.22633 (14)0.32927 (10)0.0432 (4)
C270.28819 (19)0.13376 (15)0.38488 (10)0.0487 (4)
H27A0.20440.13090.35470.058*
H27B0.36620.05340.39480.058*
C280.19174 (16)0.07798 (13)0.52451 (10)0.0414 (3)
C290.19905 (17)0.03385 (14)0.51121 (11)0.0480 (4)
H290.23780.05650.46020.058*
C300.14826 (18)0.11133 (15)0.57439 (12)0.0525 (4)
H300.15390.18670.56570.063*
C310.08990 (17)0.07942 (14)0.64945 (11)0.0476 (4)
H310.05460.13220.69080.057*
C320.08323 (15)0.03173 (13)0.66397 (10)0.0406 (3)
C330.13408 (16)0.11027 (14)0.60071 (10)0.0418 (3)
H330.12930.18530.60970.050*
C340.01855 (16)0.06187 (14)0.74681 (10)0.0441 (4)
C35A0.02175 (17)0.18781 (16)0.84834 (10)0.0504 (4)0.471 (11)
C36A0.0729 (12)0.2814 (7)0.8494 (8)0.0496 (17)0.471 (11)
H36A0.13970.29920.80740.059*0.471 (11)
C37A0.0283 (10)0.3494 (9)0.9108 (5)0.0617 (19)0.471 (11)
H37A0.06940.40860.91270.074*0.471 (11)
C38A0.0781 (10)0.3285 (7)0.9693 (5)0.0662 (19)0.471 (11)
C39A0.1328 (8)0.2360 (8)0.9690 (5)0.0677 (18)0.471 (11)
H39A0.20010.21871.01100.081*0.471 (11)
C40A0.0877 (8)0.1692 (8)0.9063 (4)0.0695 (19)0.471 (11)
H40A0.13100.11180.90310.083*0.471 (11)
Cl2A0.1473 (8)0.4066 (5)1.0500 (4)0.1195 (14)0.471 (11)
C35B0.02175 (17)0.18781 (16)0.84834 (10)0.0504 (4)0.529 (11)
C36B0.0312 (12)0.2991 (6)0.8493 (7)0.066 (3)0.529 (11)
H36B0.07260.33990.80270.079*0.529 (11)
C37B0.0201 (11)0.3507 (8)0.9187 (5)0.071 (2)0.529 (11)
H37B0.02000.42850.91760.085*0.529 (11)
C38B0.0716 (8)0.2859 (8)0.9897 (4)0.0669 (19)0.529 (11)
C39B0.0711 (9)0.1694 (9)0.9937 (4)0.0815 (19)0.529 (11)
H39B0.10170.12481.04320.098*0.529 (11)
C40B0.0239 (9)0.1210 (6)0.9220 (2)0.0703 (16)0.529 (11)
H40B0.02280.04290.92310.084*0.529 (11)
Cl2B0.1290 (5)0.3534 (9)1.0766 (3)0.1340 (18)0.529 (11)
N20.07391 (14)0.13319 (13)0.77786 (9)0.0485 (3)
O30.23884 (13)0.16234 (10)0.46603 (7)0.0513 (3)
O40.07818 (12)0.02208 (11)0.78374 (8)0.0576 (3)
H10.3037 (11)0.9519 (14)0.2221 (10)0.052 (5)*
H20.1523 (15)0.1504 (15)0.7493 (10)0.063 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.074 (3)0.056 (2)0.049 (2)0.031 (2)0.0084 (18)0.004 (2)
C2A0.059 (2)0.066 (3)0.056 (2)0.031 (2)0.0106 (19)0.014 (2)
C3A0.046 (2)0.053 (2)0.056 (3)0.0224 (19)0.008 (2)0.010 (2)
C4A0.0425 (8)0.0504 (9)0.0529 (10)0.0227 (7)0.0020 (7)0.0097 (8)
C5A0.043 (2)0.062 (3)0.056 (4)0.0161 (19)0.0025 (19)0.003 (2)
C6A0.071 (2)0.055 (3)0.060 (3)0.012 (2)0.005 (2)0.001 (2)
Cl1A0.1158 (14)0.0887 (11)0.0705 (11)0.0396 (10)0.0182 (9)0.0157 (8)
C1B0.087 (6)0.069 (6)0.079 (7)0.035 (4)0.001 (5)0.003 (5)
C2B0.059 (5)0.085 (7)0.079 (8)0.041 (5)0.019 (5)0.004 (5)
C3B0.045 (4)0.072 (7)0.073 (7)0.029 (4)0.005 (4)0.002 (5)
C4B0.0425 (8)0.0504 (9)0.0529 (10)0.0227 (7)0.0020 (7)0.0097 (8)
C5B0.069 (6)0.059 (5)0.057 (6)0.021 (4)0.001 (4)0.016 (4)
C6B0.076 (5)0.067 (6)0.074 (7)0.011 (4)0.007 (4)0.016 (5)
Cl1B0.192 (4)0.156 (4)0.163 (6)0.104 (4)0.034 (4)0.087 (4)
N10.0342 (7)0.0530 (8)0.0594 (9)0.0211 (6)0.0044 (6)0.0032 (7)
O10.0378 (6)0.0767 (9)0.0713 (8)0.0284 (6)0.0008 (5)0.0034 (7)
O20.0601 (7)0.0526 (7)0.0451 (6)0.0355 (6)0.0043 (5)0.0005 (5)
C70.0351 (8)0.0478 (9)0.0558 (10)0.0185 (7)0.0075 (7)0.0146 (8)
C80.0329 (7)0.0387 (8)0.0513 (9)0.0116 (6)0.0059 (6)0.0123 (7)
C90.0375 (8)0.0451 (9)0.0567 (10)0.0134 (7)0.0015 (7)0.0159 (8)
C100.0503 (9)0.0474 (9)0.0446 (9)0.0133 (8)0.0041 (7)0.0111 (7)
C110.0517 (9)0.0412 (9)0.0438 (9)0.0186 (7)0.0028 (7)0.0057 (7)
C120.0404 (8)0.0373 (8)0.0453 (9)0.0156 (7)0.0014 (7)0.0096 (7)
C130.0399 (8)0.0428 (9)0.0427 (9)0.0159 (7)0.0028 (6)0.0100 (7)
C140.0551 (9)0.0445 (9)0.0432 (9)0.0262 (8)0.0023 (7)0.0028 (7)
C150.0454 (8)0.0376 (8)0.0378 (8)0.0209 (7)0.0026 (6)0.0005 (7)
C160.0480 (9)0.0412 (9)0.0455 (9)0.0160 (7)0.0088 (7)0.0065 (7)
C170.0367 (8)0.0512 (10)0.0581 (10)0.0154 (7)0.0037 (7)0.0040 (8)
C180.0429 (9)0.0574 (11)0.0647 (11)0.0241 (8)0.0018 (8)0.0132 (9)
C190.0451 (9)0.0481 (9)0.0608 (11)0.0192 (7)0.0032 (8)0.0186 (8)
C200.0398 (8)0.0382 (8)0.0428 (8)0.0175 (7)0.0018 (6)0.0027 (7)
C210.0373 (8)0.0452 (9)0.0460 (9)0.0183 (7)0.0018 (6)0.0094 (7)
C220.0447 (9)0.0520 (10)0.0667 (12)0.0202 (8)0.0037 (8)0.0024 (9)
C230.0473 (10)0.0727 (13)0.0778 (13)0.0291 (10)0.0091 (9)0.0014 (11)
C240.0367 (9)0.0782 (14)0.0801 (14)0.0196 (9)0.0071 (9)0.0111 (11)
C250.0426 (9)0.0555 (11)0.0629 (11)0.0100 (8)0.0042 (8)0.0088 (9)
C260.0434 (8)0.0478 (9)0.0397 (8)0.0178 (7)0.0021 (7)0.0093 (7)
C270.0538 (9)0.0469 (9)0.0446 (9)0.0168 (8)0.0038 (7)0.0109 (7)
C280.0392 (8)0.0378 (8)0.0447 (9)0.0134 (7)0.0010 (7)0.0044 (7)
C290.0498 (9)0.0402 (9)0.0524 (10)0.0128 (7)0.0020 (7)0.0122 (8)
C300.0552 (10)0.0368 (9)0.0663 (12)0.0172 (8)0.0006 (8)0.0112 (8)
C310.0414 (8)0.0424 (9)0.0573 (10)0.0181 (7)0.0007 (7)0.0026 (8)
C320.0303 (7)0.0422 (9)0.0480 (9)0.0133 (6)0.0013 (6)0.0066 (7)
C330.0403 (8)0.0380 (8)0.0485 (9)0.0150 (7)0.0024 (7)0.0111 (7)
C340.0314 (7)0.0475 (9)0.0501 (9)0.0147 (7)0.0008 (7)0.0037 (7)
C35A0.0398 (8)0.0713 (12)0.0436 (9)0.0242 (8)0.0049 (7)0.0136 (8)
C36A0.053 (4)0.052 (3)0.042 (3)0.018 (3)0.001 (3)0.009 (3)
C37A0.067 (5)0.071 (4)0.051 (3)0.031 (3)0.004 (3)0.012 (3)
C38A0.082 (4)0.069 (4)0.051 (4)0.032 (3)0.010 (3)0.015 (3)
C39A0.064 (3)0.087 (4)0.068 (4)0.039 (3)0.033 (3)0.038 (3)
C40A0.048 (3)0.107 (4)0.082 (3)0.049 (3)0.033 (3)0.051 (3)
Cl2A0.166 (3)0.135 (3)0.091 (2)0.068 (2)0.039 (2)0.0722 (19)
C35B0.0398 (8)0.0713 (12)0.0436 (9)0.0242 (8)0.0049 (7)0.0136 (8)
C36B0.081 (6)0.058 (3)0.043 (3)0.012 (3)0.001 (3)0.003 (2)
C37B0.077 (5)0.077 (3)0.058 (3)0.019 (3)0.005 (3)0.026 (3)
C38B0.060 (3)0.101 (5)0.048 (3)0.032 (4)0.009 (2)0.029 (3)
C39B0.080 (4)0.123 (5)0.058 (3)0.056 (4)0.023 (3)0.025 (3)
C40B0.062 (4)0.105 (4)0.063 (3)0.049 (3)0.022 (2)0.032 (2)
Cl2B0.1161 (14)0.217 (5)0.083 (2)0.043 (3)0.0195 (15)0.090 (3)
N20.0418 (7)0.0659 (9)0.0470 (8)0.0310 (7)0.0128 (6)0.0149 (7)
O30.0683 (7)0.0463 (6)0.0445 (6)0.0270 (6)0.0114 (5)0.0121 (5)
O40.0440 (6)0.0703 (8)0.0654 (8)0.0330 (6)0.0127 (5)0.0118 (6)
Geometric parameters (Å, º) top
C1A—C6A1.373 (2)C21—C221.392 (2)
C1A—C2A1.375 (2)C21—C261.399 (2)
C1A—Cl1A1.735 (3)C22—C231.377 (2)
C2A—C3A1.376 (2)C22—H220.9300
C2A—H2A0.9300C23—C241.370 (3)
C3A—C4A1.378 (2)C23—H230.9300
C3A—H3A0.9300C24—C251.372 (2)
C4A—C5A1.3747 (19)C24—H240.9300
C5A—C6A1.3738 (19)C25—C261.390 (2)
C5A—H5A0.9300C25—H250.9300
C6A—H6A0.9300C26—C271.500 (2)
C1B—C6B1.373 (2)C27—O31.4239 (18)
C1B—C2B1.375 (2)C27—H27A0.9700
C1B—Cl1B1.735 (3)C27—H27B0.9700
C2B—C3B1.376 (2)C28—O31.3767 (17)
C2B—H2B0.9300C28—C331.383 (2)
C3B—H3B0.9300C28—C291.386 (2)
C5B—C6B1.373 (2)C29—C301.380 (2)
C5B—H5B0.9300C29—H290.9300
C6B—H6B0.9300C30—C311.366 (2)
N1—C71.346 (2)C30—H300.9300
N1—H10.901 (9)C31—C321.387 (2)
O1—C71.2247 (17)C31—H310.9300
O2—C121.3702 (17)C32—C331.389 (2)
O2—C141.4314 (17)C32—C341.488 (2)
C7—C81.487 (2)C33—H330.9300
C8—C131.386 (2)C34—O41.2303 (17)
C8—C91.391 (2)C34—N21.345 (2)
C9—C101.372 (2)C35A—C36A1.374 (2)
C9—H90.9300C35A—C40A1.383 (2)
C10—C111.386 (2)C35A—N21.410 (2)
C10—H100.9300C36A—C37A1.374 (2)
C11—C121.380 (2)C36A—H36A0.9300
C11—H110.9300C37A—C38A1.373 (2)
C12—C131.383 (2)C37A—H37A0.9300
C13—H130.9300C38A—C39A1.382 (2)
C14—C151.497 (2)C38A—Cl2A1.731 (3)
C14—H14A0.9700C39A—C40A1.383 (2)
C14—H14B0.9700C39A—H39A0.9300
C15—C161.387 (2)C40A—H40A0.9300
C15—C201.398 (2)C36B—C37B1.374 (2)
C16—C171.376 (2)C36B—H36B0.9300
C16—H160.9300C37B—C38B1.373 (2)
C17—C181.370 (2)C37B—H37B0.9300
C17—H170.9300C38B—C39B1.382 (2)
C18—C191.383 (2)C38B—Cl2B1.732 (3)
C18—H180.9300C39B—C40B1.383 (2)
C19—C201.388 (2)C39B—H39B0.9300
C19—H190.9300C40B—H40B0.9300
C20—C211.494 (2)N2—H20.905 (9)
C6A—C1A—C2A120.6 (5)C26—C21—C20123.74 (13)
C6A—C1A—Cl1A117.3 (5)C23—C22—C21121.43 (16)
C2A—C1A—Cl1A121.9 (5)C23—C22—H22119.3
C1A—C2A—C3A118.6 (8)C21—C22—H22119.3
C1A—C2A—H2A120.7C24—C23—C22119.83 (16)
C3A—C2A—H2A120.7C24—C23—H23120.1
C2A—C3A—C4A121.0 (8)C22—C23—H23120.1
C2A—C3A—H3A119.5C23—C24—C25119.67 (16)
C4A—C3A—H3A119.5C23—C24—H24120.2
C5A—C4A—C3A119.6 (5)C25—C24—H24120.2
C6A—C5A—C4A119.4 (6)C24—C25—C26121.69 (16)
C6A—C5A—H5A120.3C24—C25—H25119.2
C4A—C5A—H5A120.3C26—C25—H25119.2
C1A—C6A—C5A120.4 (7)C25—C26—C21118.80 (14)
C1A—C6A—H6A119.8C25—C26—C27117.51 (15)
C5A—C6A—H6A119.8C21—C26—C27123.49 (14)
C6B—C1B—C2B120.4 (12)O3—C27—C26111.81 (13)
C6B—C1B—Cl1B125.4 (11)O3—C27—H27A109.3
C2B—C1B—Cl1B113.8 (11)C26—C27—H27A109.3
C1B—C2B—C3B121.1 (16)O3—C27—H27B109.3
C1B—C2B—H2B119.5C26—C27—H27B109.3
C3B—C2B—H2B119.5H27A—C27—H27B107.9
C2B—C3B—H3B120.5O3—C28—C33116.01 (13)
C6B—C5B—H5B118.2O3—C28—C29124.31 (14)
C1B—C6B—C5B116.9 (16)C33—C28—C29119.68 (14)
C1B—C6B—H6B121.5C30—C29—C28119.35 (15)
C5B—C6B—H6B121.5C30—C29—H29120.3
C7—N1—H1117.6 (10)C28—C29—H29120.3
C12—O2—C14117.22 (11)C31—C30—C29121.23 (15)
O1—C7—N1124.04 (14)C31—C30—H30119.4
O1—C7—C8121.00 (15)C29—C30—H30119.4
N1—C7—C8114.94 (12)C30—C31—C32120.03 (14)
C13—C8—C9119.87 (14)C30—C31—H31120.0
C13—C8—C7121.17 (14)C32—C31—H31120.0
C9—C8—C7118.96 (13)C31—C32—C33119.10 (15)
C10—C9—C8119.32 (14)C31—C32—C34117.79 (13)
C10—C9—H9120.3C33—C32—C34123.10 (14)
C8—C9—H9120.3C28—C33—C32120.60 (14)
C9—C10—C11121.23 (15)C28—C33—H33119.7
C9—C10—H10119.4C32—C33—H33119.7
C11—C10—H10119.4O4—C34—N2123.28 (15)
C12—C11—C10119.25 (14)O4—C34—C32121.08 (14)
C12—C11—H11120.4N2—C34—C32115.63 (12)
C10—C11—H11120.4C36A—C35A—C40A118.5 (5)
O2—C12—C11124.68 (13)C36A—C35A—N2113.6 (4)
O2—C12—C13115.13 (13)C40A—C35A—N2127.2 (2)
C11—C12—C13120.18 (14)C37A—C36A—C35A122.0 (8)
C12—C13—C8120.12 (14)C37A—C36A—H36A119.0
C12—C13—H13119.9C35A—C36A—H36A119.0
C8—C13—H13119.9C38A—C37A—C36A118.9 (9)
O2—C14—C15108.62 (12)C38A—C37A—H37A120.5
O2—C14—H14A110.0C36A—C37A—H37A120.5
C15—C14—H14A110.0C37A—C38A—C39A120.2 (6)
O2—C14—H14B110.0C37A—C38A—Cl2A124.7 (6)
C15—C14—H14B110.0C39A—C38A—Cl2A115.0 (5)
H14A—C14—H14B108.3C38A—C39A—C40A120.0 (5)
C16—C15—C20119.12 (14)C38A—C39A—H39A120.0
C16—C15—C14119.48 (14)C40A—C39A—H39A120.0
C20—C15—C14121.40 (13)C39A—C40A—C35A120.0 (4)
C17—C16—C15121.51 (15)C39A—C40A—H40A120.0
C17—C16—H16119.2C35A—C40A—H40A120.0
C15—C16—H16119.2C37B—C36B—H36B119.8
C18—C17—C16119.57 (15)C38B—C37B—C36B119.2 (8)
C18—C17—H17120.2C38B—C37B—H37B120.4
C16—C17—H17120.2C36B—C37B—H37B120.4
C17—C18—C19119.81 (15)C37B—C38B—C39B121.8 (5)
C17—C18—H18120.1C37B—C38B—Cl2B117.1 (5)
C19—C18—H18120.1C39B—C38B—Cl2B121.0 (4)
C18—C19—C20121.42 (15)C38B—C39B—C40B118.0 (4)
C18—C19—H19119.3C38B—C39B—H39B121.0
C20—C19—H19119.3C40B—C39B—H39B121.0
C19—C20—C15118.57 (13)C39B—C40B—H40B119.6
C19—C20—C21118.54 (14)C34—N2—C35A127.85 (13)
C15—C20—C21122.66 (13)C34—N2—H2116.5 (11)
C22—C21—C26118.54 (14)C35A—N2—H2115.6 (11)
C22—C21—C20117.49 (14)C28—O3—C27116.35 (12)
C6A—C1A—C2A—C3A0.4 (16)C20—C21—C22—C23172.93 (17)
Cl1A—C1A—C2A—C3A175.5 (9)C21—C22—C23—C241.6 (3)
C1A—C2A—C3A—C4A3.1 (18)C22—C23—C24—C250.2 (3)
C2A—C3A—C4A—C5A7.1 (16)C23—C24—C25—C261.8 (3)
C3A—C4A—C5A—C6A7.5 (13)C24—C25—C26—C211.5 (3)
C2A—C1A—C6A—C5A0.1 (15)C24—C25—C26—C27173.61 (16)
Cl1A—C1A—C6A—C5A175.2 (8)C22—C21—C26—C250.3 (2)
C4A—C5A—C6A—C1A4.1 (14)C20—C21—C26—C25174.13 (15)
C6B—C1B—C2B—C3B2 (3)C22—C21—C26—C27175.11 (15)
Cl1B—C1B—C2B—C3B176 (2)C20—C21—C26—C270.7 (2)
C2B—C1B—C6B—C5B4 (3)C25—C26—C27—O3119.95 (16)
Cl1B—C1B—C6B—C5B177.7 (18)C21—C26—C27—O365.20 (19)
O1—C7—C8—C13141.98 (16)O3—C28—C29—C30179.90 (14)
N1—C7—C8—C1339.9 (2)C33—C28—C29—C300.1 (2)
O1—C7—C8—C937.6 (2)C28—C29—C30—C310.5 (2)
N1—C7—C8—C9140.53 (15)C29—C30—C31—C321.1 (2)
C13—C8—C9—C102.0 (2)C30—C31—C32—C331.1 (2)
C7—C8—C9—C10178.49 (14)C30—C31—C32—C34179.99 (14)
C8—C9—C10—C111.5 (2)O3—C28—C33—C32179.91 (13)
C9—C10—C11—C120.1 (2)C29—C28—C33—C320.1 (2)
C14—O2—C12—C119.8 (2)C31—C32—C33—C280.5 (2)
C14—O2—C12—C13170.86 (13)C34—C32—C33—C28179.32 (13)
C10—C11—C12—O2179.68 (14)C31—C32—C34—O429.4 (2)
C10—C11—C12—C131.0 (2)C33—C32—C34—O4149.42 (15)
O2—C12—C13—C8179.96 (13)C31—C32—C34—N2149.94 (14)
C11—C12—C13—C80.6 (2)C33—C32—C34—N231.2 (2)
C9—C8—C13—C120.9 (2)C40A—C35A—C36A—C37A5.7 (13)
C7—C8—C13—C12179.55 (14)N2—C35A—C36A—C37A176.8 (8)
C12—O2—C14—C15174.41 (13)C35A—C36A—C37A—C38A4.3 (15)
O2—C14—C15—C1695.68 (16)C36A—C37A—C38A—C39A3.4 (13)
O2—C14—C15—C2084.61 (17)C36A—C37A—C38A—Cl2A179.5 (9)
C20—C15—C16—C170.7 (2)C37A—C38A—C39A—C40A4.0 (12)
C14—C15—C16—C17179.01 (14)Cl2A—C38A—C39A—C40A178.6 (5)
C15—C16—C17—C180.2 (2)C38A—C39A—C40A—C35A5.5 (9)
C16—C17—C18—C190.9 (2)C36A—C35A—C40A—C39A6.2 (9)
C17—C18—C19—C200.6 (3)N2—C35A—C40A—C39A176.0 (4)
C18—C19—C20—C150.3 (2)C36B—C37B—C38B—C39B1.0 (12)
C18—C19—C20—C21174.20 (15)C36B—C37B—C38B—Cl2B177.9 (7)
C16—C15—C20—C191.0 (2)C37B—C38B—C39B—C40B3.2 (9)
C14—C15—C20—C19178.72 (13)Cl2B—C38B—C39B—C40B180.0 (5)
C16—C15—C20—C21173.33 (13)O4—C34—N2—C35A9.0 (3)
C14—C15—C20—C217.0 (2)C32—C34—N2—C35A171.68 (15)
C19—C20—C21—C22102.90 (18)C36A—C35A—N2—C34162.8 (6)
C15—C20—C21—C2271.4 (2)C40A—C35A—N2—C347.4 (6)
C19—C20—C21—C2671.6 (2)C33—C28—O3—C27175.62 (13)
C15—C20—C21—C26114.09 (17)C29—C28—O3—C274.4 (2)
C26—C21—C22—C231.9 (3)C26—C27—O3—C28175.29 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.91 (1)2.02 (1)2.8803 (16)160 (2)
N1—H1···O4ii0.90 (1)2.05 (1)2.9443 (16)170 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.905 (9)2.015 (11)2.8803 (16)159.7 (16)
N1—H1···O4ii0.901 (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 top

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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