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Acta Cryst. (2007). E63, o3967    [ doi:10.1107/S1600536807042213 ]

Ethyl 1-benzoyl-4-chloro-2-phenylprolinate

R. Tamazyan, A. Ayvazyan, A. Martirosyan, V. Martirosyan and R. Schinazi

Abstract top

The title compound, C20H20ClNO3, belongs to a family of non-nucleoside reverse transcriptase inhibitors (NNRTI). It crystallizes with two independent molecules, A and B, in the asymmetric unit. In molecule A, the pyrrolidine ring is disordered between two positions with occupancies of 0.650 (2) and 0.350 (2), corresponding to two isomers, viz. 2R,4R and 2R,4S, respectively. The disorder of the pyrrolidine ring in molecule B [occupancies 0.512 (3) and 0.488 (3)] corresponds to the other two isomers, viz. 2S,4R and 2S,4S, respectively, showing that all four possible isomers are present in the crystal structure.

Comment top

The interest to X-ray structural investigation of the title compound is stipulated by its potentially HIV-1 RT inhibition properties. This compound belongs to a family of non-nucleoside reverse transcriptase inhibitors (NNRTIs) (De Clercq, 1996) with butterfly-like conformation (Karapetyan et al., 2002; Tamazyan et al., 2002).

All four (2S,4R), (2S,4S), (2R,4R) and (2R,4 s) isomers of the title compound are present in crystal structure. The molecules crystallized in the monoclinic space group P21 with two independent molecules (Fig. 1). Each of two symmetry independent molecules corresponds to mixture of pairs of two isomers (2R,4R), (2R,4S) and (2S,4R), (2S,4S) respectively. In pair (2R,4R) (2R,4S) isomers are in ratio ~7:3, while in pair (2S,4R) (2S,4S) the isomers are in ratio ~1:1.

Related literature top

For details of the synthesis, see: Martirosyan et al. (2000, 2004). For details of the pharmacological properties of compounds of this family, see: De Clercq (1996). For crystal structures of related compounds, see: Karapetyan et al. (2002); Tamazyan et al. (2002).

Experimental top

The title compound was synthesized by cycloalkylation of ethyl-2-[2,3-dichloropropyl(phenyl)carboxamido]-2-phenylacetate in phase-transfer catalysis condition as it is described by (Martirosyan et al., 2000, 2004). The crystals were grown from ethanol solution.

Refinement top

All H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and Uiso(H) = 1.2–1.5Ueq(C). SADI and SIMI restrains were applied to positional and thermal parameters of disordered atoms in pyrrolidine rings.

Computing details top

Data collection: CAD-4 Manual (Enraf–Nonius, 1988); cell refinement: CAD-4 Manual (Enraf–Nonius, 1988); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. Two independent molecules of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Only major parts of disordered pyrrolidine rings are shown corresponding to (2S,4R) (left) and (2R,4R) (right) isomers. H atoms omitted for clarity.
Ethyl 1-benzoyl-4-chloro-2-phenylprolinate top
Crystal data top
C20H20ClNO3F000 = 752
Mr = 357.82Dx = 1.292 Mg m−3
Monoclinic, P21Melting point: 471 K
Hall symbol: P 2ybMo Kα radiation
λ = 0.71073 Å
a = 9.4241 (19) ÅCell parameters from 22 reflections
b = 10.073 (2) Åθ = 13–15º
c = 19.849 (4) ŵ = 0.23 mm−1
β = 102.52 (3)ºT = 293 (2) K
V = 1839.5 (7) Å3Irregular, colourless
Z = 40.36 × 0.32 × 0.30 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.025
Radiation source: fine-focus sealed tubeθmax = 30.0º
Monochromator: graphiteθmin = 1.1º
T = 293(2) Kh = 0→13
θ/2θ scansk = −14→14
Absorption correction: ψ scan
(North et al., 1968)		l = −27→27
Tmin = 0.875, Tmax = 0.9273 standard reflections
11300 measured reflections every 180 min
10705 independent reflections intensity decay: none
5925 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.060  w = 1/[σ2(Fo2) + (0.0523P)2 + 0.2357P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.141(Δ/σ)max = 0.003
S = 1.03Δρmax = 0.26 e Å−3
10705 reflectionsΔρmin = −0.18 e Å−3
527 parametersExtinction correction: none
478 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.06 (6)
Secondary atom site location: difference Fourier map
Crystal data top
C20H20ClNO3V = 1839.5 (7) Å3
Mr = 357.82Z = 4
Monoclinic, P21Mo Kα
a = 9.4241 (19) ŵ = 0.23 mm−1
b = 10.073 (2) ÅT = 293 (2) K
c = 19.849 (4) Å0.36 × 0.32 × 0.30 mm
β = 102.52 (3)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		5925 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.025
Tmin = 0.875, Tmax = 0.9273 standard reflections
11300 measured reflections every 180 min
10705 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.141Δρmax = 0.26 e Å−3
S = 1.03Δρmin = −0.18 e Å−3
10705 reflectionsAbsolute structure: Flack (1983), with how many Friedel pairs?
527 parametersFlack parameter: 0.06 (6)
478 restraints
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 > 2sigma(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)
ClA0.2307 (2)−0.24427 (15)0.64892 (11)0.0765 (6)0.488 (3)
C5A0.1090 (5)−0.0052 (3)0.67783 (16)0.0522 (8)0.488 (3)
H5AB0.20330.01290.70730.063*0.488 (3)
H5AA0.0433−0.03660.70580.063*0.488 (3)
C4A0.1206 (3)−0.10374 (18)0.62151 (12)0.0519 (13)0.488 (3)
H4A0.0230−0.13300.59840.062*0.488 (3)
C3A0.1874 (5)−0.0246 (5)0.5713 (2)0.0491 (8)0.488 (3)
H3AA0.2913−0.01320.58780.059*0.488 (3)
H3AB0.1681−0.06460.52580.059*0.488 (3)
ClB0.2574 (2)−0.23266 (13)0.65602 (12)0.0707 (5)0.512 (3)
C5B0.0877 (2)−0.0178 (5)0.6710 (2)0.0522 (8)0.512 (3)
H5BA0.1107−0.00820.72080.063*0.512 (3)
H5BB0.0089−0.08110.65800.063*0.512 (3)
C4B0.2200 (3)−0.06090 (19)0.64475 (10)0.0486 (12)0.512 (3)
H4B0.3051−0.00910.66740.058*0.512 (3)
C3B0.1750 (6)−0.0220 (5)0.56936 (13)0.0493 (8)0.512 (3)
H3BA0.2588−0.01400.54860.059*0.512 (3)
H3BB0.1079−0.08620.54350.059*0.512 (3)
N20.1058 (2)0.10411 (17)0.57210 (9)0.0444 (5)
C10.0469 (2)0.1191 (2)0.63468 (11)0.0465 (6)
C60.1208 (3)0.2370 (3)0.67887 (12)0.0558 (6)
O70.26410 (18)0.23518 (18)0.68232 (9)0.0657 (5)
C80.3490 (3)0.3431 (2)0.71983 (13)0.0839 (10)
H8B0.29670.38170.75210.101*
H8A0.44070.30900.74600.101*
C90.3759 (4)0.4439 (3)0.67220 (17)0.1180 (16)
H9A0.42640.40520.63990.177*
H9B0.43410.51350.69740.177*
H9C0.28500.48010.64770.177*
O100.0596 (2)0.3113 (2)0.70958 (10)0.0787 (6)
C11−0.1186 (3)0.1324 (2)0.61935 (13)0.0535 (6)
C12−0.1998 (3)0.1426 (3)0.55303 (15)0.0660 (8)
H12−0.15470.14170.51570.079*
C13−0.3520 (3)0.1544 (3)0.54218 (19)0.0855 (10)
H13−0.40770.16150.49750.103*
C14−0.4184 (3)0.1554 (3)0.5970 (2)0.0893 (11)
H14−0.51870.16510.58950.107*
C15−0.3374 (4)0.1419 (3)0.6633 (2)0.0871 (10)
H15−0.38280.14030.70050.105*
C16−0.1891 (3)0.1310 (3)0.67392 (15)0.0663 (8)
H16−0.13450.12240.71870.080*
C170.1162 (2)0.2116 (2)0.53205 (12)0.0496 (6)
C180.1774 (3)0.1935 (2)0.46970 (12)0.0495 (6)
C190.2730 (3)0.2881 (3)0.45560 (13)0.0612 (7)
H190.29880.35950.48540.073*
C200.3304 (3)0.2773 (3)0.39760 (15)0.0777 (9)
H200.39410.34190.38850.093*
C210.2949 (4)0.1739 (4)0.35388 (15)0.0849 (10)
H210.33670.16600.31570.102*
C220.1962 (4)0.0794 (3)0.36581 (15)0.0826 (10)
H220.16980.00950.33500.099*
C230.1378 (3)0.0891 (3)0.42295 (13)0.0635 (8)
H230.07130.02590.43080.076*
O240.07592 (19)0.32159 (17)0.54748 (9)0.0632 (5)
ClC0.12063 (14)0.02879 (11)0.87321 (7)0.0641 (4)0.650 (2)
C30A0.1593 (3)0.2336 (4)0.96650 (12)0.0508 (7)0.650 (2)
H30A0.18150.16251.00010.061*0.650 (2)
H30B0.05880.25990.96260.061*0.650 (2)
C29A0.18275 (19)0.18999 (18)0.90027 (13)0.0519 (10)0.650 (2)
H29A0.13320.25290.86530.062*0.650 (2)
C28A0.3450 (2)0.2071 (4)0.9068 (2)0.0449 (6)0.650 (2)
H28A0.39860.13120.92920.054*0.650 (2)
H28B0.36860.22040.86210.054*0.650 (2)
ClD0.1432 (3)0.0064 (2)0.89083 (17)0.0753 (8)0.350 (2)
C30B0.1468 (4)0.2354 (5)0.9680 (3)0.0505 (9)0.350 (2)
H30C0.11320.20221.00770.061*0.350 (2)
H30D0.06390.26320.93280.061*0.350 (2)
C29B0.2338 (3)0.1378 (3)0.94182 (19)0.0500 (18)0.350 (2)
H29B0.29450.09580.98260.060*0.350 (2)
C28B0.3383 (5)0.2067 (8)0.9050 (4)0.0450 (9)0.350 (2)
H28C0.42350.15280.90470.054*0.350 (2)
H28D0.29180.23030.85800.054*0.350 (2)
N270.37485 (18)0.32630 (18)0.94957 (9)0.0409 (4)
C260.2614 (2)0.3526 (2)0.98875 (11)0.0411 (5)
C310.1797 (2)0.4832 (2)0.96391 (13)0.0490 (6)
O320.16150 (18)0.49700 (18)0.89589 (9)0.0601 (5)
C330.0942 (3)0.6224 (3)0.86960 (12)0.0808 (9)
H33A−0.00740.62270.87240.097*
H33B0.14260.69550.89710.097*
C340.1062 (5)0.6376 (4)0.79866 (14)0.1121 (13)
H34A0.20690.64340.79670.168*
H34B0.05680.71710.77990.168*
H34C0.06280.56240.77230.168*
O350.1314 (2)0.55831 (19)0.99991 (10)0.0706 (5)
C360.3196 (2)0.3580 (2)1.06703 (11)0.0443 (5)
C370.4658 (3)0.3550 (2)1.09670 (12)0.0518 (6)
H370.53290.34811.06870.062*
C380.5144 (3)0.3623 (3)1.16785 (13)0.0673 (8)
H380.61340.36141.18740.081*
C390.4150 (4)0.3707 (3)1.20928 (14)0.0748 (9)
H390.44710.37581.25690.090*
C400.2698 (4)0.3717 (3)1.18081 (14)0.0741 (8)
H400.20300.37681.20900.089*
C410.2218 (3)0.3650 (3)1.10988 (13)0.0578 (7)
H410.12250.36511.09070.069*
C420.4682 (2)0.4255 (2)0.94158 (11)0.0423 (5)
C430.5815 (2)0.3977 (2)0.90132 (11)0.0416 (5)
C440.6580 (2)0.2789 (2)0.90635 (12)0.0510 (6)
H440.63770.21150.93490.061*
C450.7639 (3)0.2612 (3)0.86901 (14)0.0619 (7)
H450.81600.18220.87310.074*
C460.7935 (3)0.3590 (3)0.82573 (14)0.0662 (8)
H460.86290.34490.79950.079*
C470.7198 (3)0.4781 (3)0.82140 (14)0.0611 (7)
H470.74060.54540.79300.073*
C480.6145 (3)0.4970 (2)0.85964 (12)0.0526 (6)
H480.56570.57760.85710.063*
O490.45967 (17)0.53440 (16)0.96811 (8)0.0525 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
ClA0.1017 (12)0.0510 (8)0.0724 (10)0.0228 (9)0.0096 (9)0.0096 (8)
C5A0.0620 (16)0.0495 (15)0.0422 (15)0.0035 (14)0.0049 (14)0.0008 (13)
C4A0.065 (3)0.039 (2)0.047 (3)0.004 (2)0.001 (2)−0.002 (2)
C3A0.0587 (15)0.0433 (14)0.0461 (14)0.0072 (13)0.0130 (13)0.0014 (13)
ClB0.0894 (11)0.0492 (8)0.0690 (10)0.0161 (8)0.0074 (9)0.0114 (8)
C5B0.0619 (16)0.0492 (15)0.0427 (15)0.0040 (14)0.0049 (14)0.0013 (13)
C4B0.058 (3)0.040 (2)0.045 (3)0.005 (2)0.005 (2)0.0037 (19)
C3B0.0592 (15)0.0434 (14)0.0460 (14)0.0071 (13)0.0129 (13)0.0013 (12)
N20.0533 (11)0.0383 (9)0.0418 (10)0.0074 (8)0.0106 (8)−0.0008 (8)
C10.0525 (13)0.0431 (12)0.0456 (12)0.0020 (10)0.0146 (10)0.0024 (10)
C60.0608 (14)0.0561 (15)0.0508 (13)−0.0007 (12)0.0124 (11)−0.0097 (11)
O70.0565 (10)0.0642 (11)0.0733 (11)−0.0020 (9)0.0077 (9)−0.0194 (9)
C80.0738 (18)0.083 (2)0.090 (2)−0.0084 (17)0.0052 (16)−0.0283 (18)
C90.123 (3)0.0574 (19)0.150 (4)−0.015 (2)−0.022 (3)0.005 (2)
O100.0799 (12)0.0732 (12)0.0892 (12)−0.0046 (10)0.0318 (10)−0.0367 (10)
C110.0533 (13)0.0443 (12)0.0625 (15)0.0039 (11)0.0118 (12)−0.0029 (11)
C120.0531 (15)0.0670 (16)0.0745 (18)0.0062 (13)0.0059 (13)0.0021 (14)
C130.0629 (18)0.086 (2)0.100 (2)0.0059 (16)−0.0004 (17)0.0073 (19)
C140.0501 (16)0.082 (2)0.137 (3)0.0083 (15)0.0226 (18)−0.004 (2)
C150.0699 (18)0.081 (2)0.120 (3)0.0031 (16)0.0416 (18)−0.0055 (19)
C160.0635 (16)0.0672 (17)0.0742 (17)0.0044 (13)0.0281 (13)−0.0060 (14)
C170.0469 (12)0.0443 (12)0.0545 (14)0.0005 (10)0.0043 (11)0.0028 (10)
C180.0543 (13)0.0485 (12)0.0437 (12)0.0044 (11)0.0064 (11)0.0098 (10)
C190.0700 (16)0.0573 (16)0.0555 (14)−0.0004 (12)0.0120 (13)0.0088 (11)
C200.0855 (19)0.080 (2)0.0714 (18)−0.0111 (17)0.0253 (15)0.0161 (16)
C210.113 (2)0.095 (2)0.0530 (16)−0.007 (2)0.0319 (17)0.0052 (16)
C220.122 (3)0.079 (2)0.0484 (16)−0.0094 (19)0.0223 (16)−0.0092 (14)
C230.0758 (17)0.0649 (16)0.0465 (14)−0.0104 (14)0.0062 (13)0.0035 (12)
O240.0763 (11)0.0434 (9)0.0706 (11)0.0116 (9)0.0176 (9)0.0036 (8)
ClC0.0604 (6)0.0631 (6)0.0698 (7)−0.0207 (5)0.0168 (5)−0.0220 (5)
C30A0.0422 (13)0.0531 (14)0.0588 (14)−0.0083 (12)0.0144 (12)−0.0077 (12)
C29A0.0456 (19)0.055 (2)0.054 (2)−0.0075 (17)0.0071 (17)−0.0024 (17)
C28A0.0437 (12)0.0430 (12)0.0497 (13)−0.0070 (11)0.0137 (11)−0.0062 (11)
ClD0.0652 (13)0.0575 (12)0.1014 (18)−0.0216 (11)0.0140 (12)−0.0222 (12)
C30B0.0420 (16)0.0527 (17)0.0582 (16)−0.0079 (15)0.0142 (15)−0.0080 (15)
C29B0.041 (3)0.043 (3)0.058 (4)−0.012 (3)−0.006 (3)−0.004 (3)
C28B0.0440 (15)0.0429 (15)0.0496 (16)−0.0071 (14)0.0136 (14)−0.0064 (14)
N270.0388 (9)0.0394 (9)0.0458 (9)−0.0011 (8)0.0117 (8)−0.0005 (8)
C260.0382 (10)0.0408 (11)0.0456 (11)0.0008 (9)0.0122 (9)0.0001 (9)
C310.0420 (12)0.0501 (13)0.0558 (14)−0.0004 (10)0.0128 (11)0.0011 (11)
O320.0611 (10)0.0619 (10)0.0561 (10)0.0168 (9)0.0098 (8)0.0119 (8)
C330.082 (2)0.0752 (19)0.082 (2)0.0255 (16)0.0124 (16)0.0243 (16)
C340.159 (3)0.096 (3)0.086 (2)0.032 (3)0.036 (2)0.033 (2)
O350.0787 (11)0.0618 (11)0.0754 (12)0.0242 (9)0.0258 (10)−0.0020 (9)
C360.0508 (12)0.0368 (11)0.0468 (12)−0.0022 (10)0.0140 (10)−0.0007 (9)
C370.0508 (13)0.0571 (14)0.0484 (12)−0.0038 (11)0.0123 (11)0.0038 (11)
C380.0686 (17)0.0745 (18)0.0527 (15)−0.0119 (14)−0.0006 (13)0.0069 (14)
C390.101 (2)0.0788 (19)0.0420 (14)−0.0110 (17)0.0107 (15)0.0008 (13)
C400.100 (2)0.0754 (19)0.0571 (15)0.0012 (17)0.0401 (15)−0.0006 (13)
C410.0609 (14)0.0604 (15)0.0563 (14)0.0036 (12)0.0222 (12)0.0001 (12)
C420.0404 (12)0.0431 (11)0.0420 (12)0.0000 (9)0.0060 (10)0.0037 (10)
C430.0375 (11)0.0430 (11)0.0423 (12)−0.0057 (9)0.0043 (9)−0.0037 (9)
C440.0458 (12)0.0488 (13)0.0605 (14)−0.0018 (11)0.0160 (11)0.0045 (11)
C450.0434 (12)0.0550 (13)0.0896 (18)0.0077 (12)0.0197 (13)−0.0027 (15)
C460.0548 (14)0.0804 (19)0.0701 (16)−0.0030 (14)0.0284 (12)−0.0092 (15)
C470.0635 (15)0.0665 (16)0.0583 (15)−0.0052 (13)0.0241 (12)0.0096 (12)
C480.0537 (13)0.0471 (13)0.0581 (14)0.0008 (11)0.0145 (12)0.0046 (11)
O490.0587 (9)0.0416 (8)0.0604 (10)−0.0070 (7)0.0202 (8)−0.0066 (8)
Geometric parameters (Å, °) top
ClA—C4A1.7701 (18)ClC—C29A1.7697 (17)
C5A—C4A1.516 (2)C30A—C29A1.448 (2)
C5A—C11.559 (4)C30A—C261.541 (4)
C5A—H5AB0.9700C30A—H30A0.9700
C5A—H5AA0.9700C30A—H30B0.9700
C4A—C3A1.516 (2)C29A—C28A1.516 (2)
C4A—H4A0.9800C29A—H29A0.9800
C3A—N21.510 (5)C28A—N271.462 (5)
C3A—H3AA0.9700C28A—H28A0.9700
C3A—H3AB0.9700C28A—H28B0.9700
ClB—C4B1.7702 (18)ClD—C29B1.769 (2)
C5B—C4B1.516 (2)C30B—C29B1.447 (3)
C5B—C11.565 (5)C30B—C261.593 (5)
C5B—H5BA0.9700C30B—H30C0.9700
C5B—H5BB0.9700C30B—H30D0.9700
C4B—C3B1.516 (2)C29B—C28B1.516 (2)
C4B—H4B0.9800C29B—H29B0.9800
C3B—N21.434 (6)C28B—N271.490 (9)
C3B—H3BA0.9700C28B—H28C0.9700
C3B—H3BB0.9700C28B—H28D0.9700
N2—C171.359 (3)N27—C421.363 (3)
N2—C11.474 (3)N27—C261.476 (3)
C1—C111.528 (3)C26—C361.532 (3)
C1—C61.549 (3)C26—C311.549 (3)
C6—O101.191 (3)C31—O351.196 (3)
C6—O71.338 (3)C31—O321.331 (3)
O7—C81.455 (3)O32—C331.458 (3)
C8—C91.447 (2)C33—C341.445 (2)
C8—H8B0.9700C33—H33A0.9700
C8—H8A0.9700C33—H33B0.9700
C9—H9A0.9600C34—H34A0.9600
C9—H9B0.9600C34—H34B0.9600
C9—H9C0.9600C34—H34C0.9600
C11—C121.376 (4)C36—C371.376 (3)
C11—C161.388 (4)C36—C411.385 (3)
C12—C131.408 (4)C37—C381.389 (4)
C12—H120.9300C37—H370.9300
C13—C141.368 (5)C38—C391.377 (4)
C13—H130.9300C38—H380.9300
C14—C151.377 (5)C39—C401.362 (4)
C14—H140.9300C39—H390.9300
C15—C161.372 (4)C40—C411.384 (4)
C15—H150.9300C40—H400.9300
C16—H160.9300C41—H410.9300
C17—O241.231 (3)C42—O491.227 (3)
C17—C181.486 (4)C42—C431.493 (3)
C18—C191.381 (4)C43—C481.376 (3)
C18—C231.399 (3)C43—C441.389 (3)
C19—C201.378 (4)C44—C451.378 (3)
C19—H190.9300C44—H440.9300
C20—C211.351 (4)C45—C461.375 (4)
C20—H200.9300C45—H450.9300
C21—C221.387 (5)C46—C471.380 (4)
C21—H210.9300C46—H460.9300
C22—C231.367 (4)C47—C481.386 (4)
C22—H220.9300C47—H470.9300
C23—H230.9300C48—H480.9300
C4A—C5A—C1101.5 (2)C29A—C30A—C26106.7 (2)
C4A—C5A—H5AB111.5C29A—C30A—H30A110.4
C1—C5A—H5AB111.5C26—C30A—H30A110.4
C4A—C5A—H5AA111.5C29A—C30A—H30B110.4
C1—C5A—H5AA111.5C26—C30A—H30B110.4
H5AB—C5A—H5AA109.3H30A—C30A—H30B108.6
C3A—C4A—C5A104.3 (3)C30A—C29A—C28A103.8 (3)
C3A—C4A—ClA108.8 (2)C30A—C29A—ClC116.6 (2)
C5A—C4A—ClA115.3 (2)C28A—C29A—ClC113.0 (2)
C3A—C4A—H4A109.4C30A—C29A—H29A107.7
C5A—C4A—H4A109.4C28A—C29A—H29A107.7
ClA—C4A—H4A109.4ClC—C29A—H29A107.7
N2—C3A—C4A99.2 (3)N27—C28A—C29A101.9 (2)
N2—C3A—H3AA111.9N27—C28A—H28A111.4
C4A—C3A—H3AA111.9C29A—C28A—H28A111.4
N2—C3A—H3AB111.9N27—C28A—H28B111.4
C4A—C3A—H3AB111.9C29A—C28A—H28B111.4
H3AA—C3A—H3AB109.6H28A—C28A—H28B109.3
C4B—C5B—C1103.4 (3)C29B—C30B—C26101.0 (2)
C4B—C5B—H5BA111.1C29B—C30B—H30C111.6
C1—C5B—H5BA111.1C26—C30B—H30C111.6
C4B—C5B—H5BB111.1C29B—C30B—H30D111.6
C1—C5B—H5BB111.1C26—C30B—H30D111.6
H5BA—C5B—H5BB109.0H30C—C30B—H30D109.4
C3B—C4B—C5B101.0 (3)C30B—C29B—C28B109.9 (4)
C3B—C4B—ClB112.5 (3)C30B—C29B—ClD118.2 (3)
C5B—C4B—ClB113.1 (3)C28B—C29B—ClD110.5 (4)
C3B—C4B—H4B110.0C30B—C29B—H29B105.8
C5B—C4B—H4B110.0C28B—C29B—H29B105.8
ClB—C4B—H4B110.0ClD—C29B—H29B105.8
N2—C3B—C4B102.9 (3)N27—C28B—C29B100.0 (4)
N2—C3B—H3BA111.2N27—C28B—H28C111.8
C4B—C3B—H3BA111.2C29B—C28B—H28C111.8
N2—C3B—H3BB111.2N27—C28B—H28D111.8
C4B—C3B—H3BB111.2C29B—C28B—H28D111.8
H3BA—C3B—H3BB109.1H28C—C28B—H28D109.5
C17—N2—C3B126.3 (2)C42—N27—C28A125.6 (2)
C17—N2—C1119.94 (18)C42—N27—C26119.27 (18)
C3B—N2—C1112.4 (2)C28A—N27—C26112.56 (17)
C17—N2—C3A125.2 (2)C42—N27—C28B126.5 (2)
C1—N2—C3A112.52 (19)C26—N27—C28B111.0 (2)
N2—C1—C11113.30 (18)N27—C26—C36113.57 (17)
N2—C1—C6110.52 (19)N27—C26—C30A100.82 (18)
C11—C1—C6111.10 (19)C36—C26—C30A112.45 (19)
N2—C1—C5A102.4 (2)N27—C26—C31110.59 (18)
C11—C1—C5A115.2 (2)C36—C26—C31109.67 (18)
C6—C1—C5A103.64 (19)C30A—C26—C31109.43 (19)
N2—C1—C5B101.4 (2)N27—C26—C30B105.0 (2)
C11—C1—C5B107.86 (19)C36—C26—C30B111.2 (3)
C6—C1—C5B112.3 (2)C31—C26—C30B106.5 (2)
O10—C6—O7125.3 (2)O35—C31—O32123.9 (2)
O10—C6—C1124.3 (2)O35—C31—C26125.0 (2)
O7—C6—C1110.1 (2)O32—C31—C26110.95 (19)
C6—O7—C8116.9 (2)C31—O32—C33113.84 (19)
C9—C8—O7110.2 (2)C34—C33—O32108.7 (2)
C9—C8—H8B109.6C34—C33—H33A110.0
O7—C8—H8B109.6O32—C33—H33A110.0
C9—C8—H8A109.6C34—C33—H33B110.0
O7—C8—H8A109.6O32—C33—H33B110.0
H8B—C8—H8A108.1H33A—C33—H33B108.3
C8—C9—H9A109.5C33—C34—H34A109.5
C8—C9—H9B109.5C33—C34—H34B109.5
H9A—C9—H9B109.5H34A—C34—H34B109.5
C8—C9—H9C109.5C33—C34—H34C109.5
H9A—C9—H9C109.5H34A—C34—H34C109.5
H9B—C9—H9C109.5H34B—C34—H34C109.5
C12—C11—C16119.1 (2)C37—C36—C41118.4 (2)
C12—C11—C1122.0 (2)C37—C36—C26122.5 (2)
C16—C11—C1119.0 (2)C41—C36—C26119.0 (2)
C11—C12—C13119.3 (3)C36—C37—C38120.8 (2)
C11—C12—H12120.3C36—C37—H37119.6
C13—C12—H12120.3C38—C37—H37119.6
C14—C13—C12120.3 (3)C39—C38—C37119.6 (3)
C14—C13—H13119.8C39—C38—H38120.2
C12—C13—H13119.8C37—C38—H38120.2
C13—C14—C15120.4 (3)C40—C39—C38120.3 (3)
C13—C14—H14119.8C40—C39—H39119.8
C15—C14—H14119.8C38—C39—H39119.8
C16—C15—C14119.3 (3)C39—C40—C41120.0 (3)
C16—C15—H15120.3C39—C40—H40120.0
C14—C15—H15120.3C41—C40—H40120.0
C15—C16—C11121.6 (3)C40—C41—C36120.8 (3)
C15—C16—H16119.2C40—C41—H41119.6
C11—C16—H16119.2C36—C41—H41119.6
O24—C17—N2120.4 (2)O49—C42—N27120.1 (2)
O24—C17—C18120.9 (2)O49—C42—C43121.2 (2)
N2—C17—C18118.7 (2)N27—C42—C43118.68 (19)
C19—C18—C23118.5 (2)C48—C43—C44119.2 (2)
C19—C18—C17118.2 (2)C48—C43—C42117.8 (2)
C23—C18—C17123.3 (2)C44—C43—C42122.9 (2)
C20—C19—C18120.4 (3)C45—C44—C43119.9 (2)
C20—C19—H19119.8C45—C44—H44120.1
C18—C19—H19119.8C43—C44—H44120.1
C21—C20—C19120.7 (3)C46—C45—C44120.8 (3)
C21—C20—H20119.7C46—C45—H45119.6
C19—C20—H20119.7C44—C45—H45119.6
C20—C21—C22120.1 (3)C45—C46—C47119.6 (3)
C20—C21—H21119.9C45—C46—H46120.2
C22—C21—H21119.9C47—C46—H46120.2
C23—C22—C21119.8 (3)C46—C47—C48119.7 (2)
C23—C22—H22120.1C46—C47—H47120.2
C21—C22—H22120.1C48—C47—H47120.2
C22—C23—C18120.5 (3)C43—C48—C47120.8 (2)
C22—C23—H23119.8C43—C48—H48119.6
C18—C23—H23119.8C47—C48—H48119.6
C1—C5A—C4A—C3A44.9 (3)C26—C30A—C29A—C28A37.6 (3)
C1—C5A—C4A—ClA164.2 (2)C26—C30A—C29A—ClC162.62 (17)
C5A—C4A—C3A—N2−40.5 (3)C30A—C29A—C28A—N27−35.1 (3)
ClA—C4A—C3A—N2−164.10 (19)ClC—C29A—C28A—N27−162.4 (2)
C1—C5B—C4B—C3B−41.5 (3)C26—C30B—C29B—C28B−35.2 (5)
C1—C5B—C4B—ClB−161.96 (19)C26—C30B—C29B—ClD−163.2 (3)
C5B—C4B—C3B—N240.8 (4)C30B—C29B—C28B—N2736.4 (5)
ClB—C4B—C3B—N2161.7 (3)ClD—C29B—C28B—N27168.6 (3)
C4B—C3B—N2—C17141.0 (3)C29A—C28A—N27—C42−140.9 (2)
C4B—C3B—N2—C1−25.4 (4)C29A—C28A—N27—C2620.6 (3)
C4B—C3B—N2—C3A68 (3)C29A—C28A—N27—C28B−26 (7)
C4A—C3A—N2—C17−175.8 (2)C29B—C28B—N27—C42179.0 (2)
C4A—C3A—N2—C3B−66 (3)C29B—C28B—N27—C28A112 (7)
C4A—C3A—N2—C121.7 (3)C29B—C28B—N27—C26−21.7 (4)
C17—N2—C1—C1176.7 (2)C42—N27—C26—C36−75.4 (2)
C3B—N2—C1—C11−116.0 (3)C28A—N27—C26—C36121.8 (2)
C3A—N2—C1—C11−119.8 (3)C28B—N27—C26—C36123.6 (3)
C17—N2—C1—C6−48.8 (3)C42—N27—C26—C30A164.10 (19)
C3B—N2—C1—C6118.6 (3)C28A—N27—C26—C30A1.3 (3)
C3A—N2—C1—C6114.8 (3)C28B—N27—C26—C30A3.1 (3)
C17—N2—C1—C5A−158.7 (2)C42—N27—C26—C3148.4 (2)
C3B—N2—C1—C5A8.7 (3)C28A—N27—C26—C31−114.4 (2)
C3A—N2—C1—C5A4.9 (3)C28B—N27—C26—C31−112.6 (3)
C17—N2—C1—C5B−168.0 (2)C42—N27—C26—C30B162.9 (3)
C3B—N2—C1—C5B−0.7 (3)C28A—N27—C26—C30B0.1 (3)
C3A—N2—C1—C5B−4.5 (3)C28B—N27—C26—C30B1.9 (4)
C4A—C5A—C1—N2−29.6 (3)C29A—C30A—C26—N27−24.3 (3)
C4A—C5A—C1—C1193.8 (3)C29A—C30A—C26—C36−145.6 (2)
C4A—C5A—C1—C6−144.7 (3)C29A—C30A—C26—C3192.3 (3)
C4A—C5A—C1—C5B55.1 (11)C29A—C30A—C26—C30B140 (4)
C4B—C5B—C1—N226.5 (3)C29B—C30B—C26—N2719.8 (4)
C4B—C5B—C1—C11145.8 (2)C29B—C30B—C26—C36−103.5 (4)
C4B—C5B—C1—C6−91.5 (3)C29B—C30B—C26—C30A4(4)
C4B—C5B—C1—C5A−70.7 (11)C29B—C30B—C26—C31137.1 (3)
N2—C1—C6—O10142.2 (2)N27—C26—C31—O35−146.5 (2)
C11—C1—C6—O1015.5 (3)C36—C26—C31—O35−20.5 (3)
C5A—C1—C6—O10−108.7 (3)C30A—C26—C31—O35103.3 (3)
C5B—C1—C6—O10−105.4 (3)C30B—C26—C31—O3599.9 (3)
N2—C1—C6—O7−43.4 (3)N27—C26—C31—O3237.6 (2)
C11—C1—C6—O7−170.0 (2)C36—C26—C31—O32163.61 (18)
C5A—C1—C6—O765.7 (3)C30A—C26—C31—O32−72.6 (2)
C5B—C1—C6—O769.1 (3)C30B—C26—C31—O32−75.9 (3)
O10—C6—O7—C8−8.1 (4)O35—C31—O32—C338.1 (3)
C1—C6—O7—C8177.55 (19)C26—C31—O32—C33−176.0 (2)
C6—O7—C8—C9−98.2 (3)C31—O32—C33—C34168.8 (3)
N2—C1—C11—C12−6.2 (3)N27—C26—C36—C377.7 (3)
C6—C1—C11—C12118.9 (3)C30A—C26—C36—C37121.3 (2)
C5A—C1—C11—C12−123.6 (3)C31—C26—C36—C37−116.6 (2)
C5B—C1—C11—C12−117.6 (3)C30B—C26—C36—C37125.8 (2)
N2—C1—C11—C16172.3 (2)N27—C26—C36—C41−171.8 (2)
C6—C1—C11—C16−62.6 (3)C30A—C26—C36—C41−58.1 (3)
C5A—C1—C11—C1654.8 (3)C31—C26—C36—C4163.9 (3)
C5B—C1—C11—C1660.8 (3)C30B—C26—C36—C41−53.6 (3)
C16—C11—C12—C131.4 (4)C41—C36—C37—C38−1.6 (4)
C1—C11—C12—C13179.9 (2)C26—C36—C37—C38178.9 (2)
C11—C12—C13—C14−0.2 (5)C36—C37—C38—C390.9 (4)
C12—C13—C14—C15−1.4 (5)C37—C38—C39—C400.2 (4)
C13—C14—C15—C161.6 (5)C38—C39—C40—C41−0.4 (5)
C14—C15—C16—C11−0.3 (5)C39—C40—C41—C36−0.3 (4)
C12—C11—C16—C15−1.2 (4)C37—C36—C41—C401.4 (4)
C1—C11—C16—C15−179.7 (3)C26—C36—C41—C40−179.2 (2)
C3B—N2—C17—O24−165.9 (3)C28A—N27—C42—O49162.0 (2)
C1—N2—C17—O24−0.4 (3)C26—N27—C42—O491.6 (3)
C3A—N2—C17—O24−161.7 (3)C28B—N27—C42—O49159.4 (4)
C3B—N2—C17—C1813.9 (4)C28A—N27—C42—C43−19.1 (3)
C1—N2—C17—C18179.39 (19)C26—N27—C42—C43−179.48 (18)
C3A—N2—C17—C1818.1 (4)C28B—N27—C42—C43−21.7 (4)
O24—C17—C18—C1941.8 (3)O49—C42—C43—C48−38.8 (3)
N2—C17—C18—C19−138.0 (2)N27—C42—C43—C48142.4 (2)
O24—C17—C18—C23−135.0 (3)O49—C42—C43—C44138.7 (2)
N2—C17—C18—C2345.2 (3)N27—C42—C43—C44−40.2 (3)
C23—C18—C19—C20−1.6 (4)C48—C43—C44—C45−0.9 (3)
C17—C18—C19—C20−178.6 (2)C42—C43—C44—C45−178.3 (2)
C18—C19—C20—C21−0.4 (4)C43—C44—C45—C46−1.1 (4)
C19—C20—C21—C222.1 (5)C44—C45—C46—C472.2 (4)
C20—C21—C22—C23−1.8 (5)C45—C46—C47—C48−1.3 (4)
C21—C22—C23—C18−0.3 (5)C44—C43—C48—C471.8 (3)
C19—C18—C23—C221.9 (4)C42—C43—C48—C47179.4 (2)
C17—C18—C23—C22178.8 (3)C46—C47—C48—C43−0.7 (4)
Acknowledgements top

This research was supported by the Civilian Research and Development Foundation (CRDF), USA? (grant No. ARB2–2701-YE-05).

references
References top

Bruker (2000). SHELXTL-NT. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.

De Clercq, E. (1996). Rev. Med. Virol. 6, 97–117.

Enraf–Nonius (1988). CAD-4 Manual. Version 5.0. Enraf–Nonius, Delft, The Netherlands.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.

Karapetyan, H., Tamazyan, R., Martirosyan, A., Hovhannesyan, V. & Gasparyan, S. (2002). Acta Cryst. C58, o399–o401.

Martirosyan, A. O., Gasparyan, S. P., Oganesyan, V. E., Mndzhoyan, Sh. L., Alexanyan, M. L., Nikishchenko, M. N. & Babayan, G. Sh. (2000). Chem. Heterocycl. Compd. 36, 416–419.

Martirosyan, A. O., Hovhannesyan, V. E., Gasparyan, S. P., Karapetyan, H. A., Panosyan, G. A. & Martirosyan, V. O. (2004). Chem. Heterocycl. Compd. 40, 1007–1008.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Spek, A. L. (1997). HELENA. University of Utrecht, The Netherlands.

Tamazyan, R., Karapetyan, H., Martirosyan, A., Hovhannesyan, V. & Gasparyan, S. (2002). Acta Cryst. C58, o386–o388.