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Acta Cryst. (2007). E63, o4069
https://doi.org/10.1107/S1600536807043875
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cis-1-Benzoyl-2-(2-benz­yloxy-5-chloro­phen­yl)-4-chloro­pyrrolidine-2-carbo­nitrile

R. Tamazyan, L. Matevosyan, A. Martirosyan, S. Gasparyan and R. Schinazi
In the title compound, C25H20Cl2N2O2, which is a potential anti-human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse transcriptase inhibitor (NNRTI), the pyrrolidine ring has as envelope conformation. Centrosymmetric dimers of mol­ecules appear to associate via short N...Cl inter­actions [3.205 (2) Å].
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043875/hb2520sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043875/hb2520Isup2.hkl
Contains datablock I

CCDC reference: 663774

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.131
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C20     ..       5.12 su
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl31   ..  N21     ..       3.20 Ang.


Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_1_G Check the Absolute Configuration of C1     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C4     = ...          R


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

The title compound, (I), (Fig. 1) has potential HIV-1 RT (reverse transcriptase) inhibition properties. These compounds belong to the non-nucleoside reverse transcriptase inhibitor (NNRTI) family.

All the bond lengths and angles in (I) are in good agreement with their reference values (Allen et al., 1995), expect the C1—C20 bond length [1.491 (2) Å], which is shorter than its mean value. The arbitrarily chosen asymmetric molecule is chiral (C1 S, C4 R configuration) but crystal symmetry generates a racemic mixture.

Most features of the packing for (I) (Fig. 2) can be ascribed to Van der Vaals interactions. However, the interatomic distance N21···Cl31 [3.205 (2) Å] is slightly shorter than the sum of Van der Vaals radii of N and Cl atoms (3.30 Å) and might be considered as the linker in a weakly bonded centrosymmeric dimmer (Fig. 3).

We believe that shortening of the C1—C20 bond length and the short N···Cl intermolecular distance could be explained by some polarization effects caused by the triple C20 ≡N21 bond.

Related literature top

For synthesis, see: Martirosyan et al., (2000, 2004). For reference structural data, see: Allen et al. (1995). For related literature, see: Johnson (1976).

Experimental top

The title compound was synthesized by cycloalkylation of 2-benzyloxy-5-chloro-1-cyano[2,3-dichloropropyl(phenyl)carboxamido]methylbenzene in phase-transfer catalysis condition as described by Martirosyan et al. (2000, 2004). The compound as synthesized is a racemate. Colourless prisms of (I) were grown from an ethanol solution.

Refinement top

The H atom positions were determined from difference maps and their positions and Uiso values were freely reifned.

Structure description top

The title compound, (I), (Fig. 1) has potential HIV-1 RT (reverse transcriptase) inhibition properties. These compounds belong to the non-nucleoside reverse transcriptase inhibitor (NNRTI) family.

All the bond lengths and angles in (I) are in good agreement with their reference values (Allen et al., 1995), expect the C1—C20 bond length [1.491 (2) Å], which is shorter than its mean value. The arbitrarily chosen asymmetric molecule is chiral (C1 S, C4 R configuration) but crystal symmetry generates a racemic mixture.

Most features of the packing for (I) (Fig. 2) can be ascribed to Van der Vaals interactions. However, the interatomic distance N21···Cl31 [3.205 (2) Å] is slightly shorter than the sum of Van der Vaals radii of N and Cl atoms (3.30 Å) and might be considered as the linker in a weakly bonded centrosymmeric dimmer (Fig. 3).

We believe that shortening of the C1—C20 bond length and the short N···Cl intermolecular distance could be explained by some polarization effects caused by the triple C20 ≡N21 bond.

For synthesis, see: Martirosyan et al., (2000, 2004). For reference structural data, see: Allen et al. (1995). For related literature, see: Johnson (1976).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level (H atoms omitted for clarity).
[Figure 2] Fig. 2. Unit cell packing for (I).
[Figure 3] Fig. 3. A centrosymmeric dimer connected via N···Cl interactions. Symmetry code: (i) -x, 3 - y, 1 - z.
cis-1-Benzoyl-2-(2-benzyloxy-5-chlorophenyl)-4- chloropyrrolidine-2-carbonitrile top
Crystal data top
C25H20Cl2N2O2Z = 2
Mr = 451.33F(000) = 468
Triclinic, P1Dx = 1.364 Mg m−3
Hall symbol: -P 1Melting point: 470 K
a = 9.803 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.653 (2) ÅCell parameters from 24 reflections
c = 12.364 (3) Åθ = 8–19°
α = 72.12 (3)°µ = 0.32 mm−1
β = 85.82 (3)°T = 293 K
γ = 63.71 (3)°Prism, colourless
V = 1098.7 (5) Å30.35 × 0.28 × 0.22 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.022
Radiation source: fine-focus sealed tubeθmax = 28.0°, θmin = 1.7°
Graphite monochromatorh = −12→12
θ/2θ scansk = −13→14
5515 measured reflectionsl = 0→16
5275 independent reflections3 standard reflections every 180 min
4051 reflections with I > 2σ(I) intensity decay: none
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)] = 0.046Hydrogen site location: difference Fourier map
wR(F2) = 0.131All H-atom parameters refined
S = 1.03 w = 1/[σ2(Fo2) + (0.061P)2 + 0.5189P]
where P = (Fo2 + 2Fc2)/3
5275 reflections(Δ/σ)max < 0.001
360 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.50 e Å−3
Crystal data top
C25H20Cl2N2O2γ = 63.71 (3)°
Mr = 451.33V = 1098.7 (5) Å3
Triclinic, P1Z = 2
a = 9.803 (2) ÅMo Kα radiation
b = 10.653 (2) ŵ = 0.32 mm−1
c = 12.364 (3) ÅT = 293 K
α = 72.12 (3)°0.35 × 0.28 × 0.22 mm
β = 85.82 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.022
5515 measured reflections3 standard reflections every 180 min
5275 independent reflections intensity decay: none
4051 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.131All H-atom parameters refined
S = 1.03Δρmax = 0.29 e Å−3
5275 reflectionsΔρmin = −0.50 e Å−3
360 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
xyzUiso*/Ueq
Cl31−0.02327 (7)1.42050 (6)0.34471 (6)0.05911 (19)
Cl300.60429 (8)0.90398 (7)0.89834 (6)0.06254 (19)
C10.33489 (19)1.00696 (18)0.69407 (15)0.0295 (3)
N20.32236 (16)0.88563 (15)0.78477 (12)0.0293 (3)
C30.4723 (2)0.7608 (2)0.82939 (19)0.0362 (4)
C40.5823 (2)0.8276 (2)0.79414 (19)0.0415 (4)
C50.5093 (2)0.9450 (2)0.68135 (18)0.0383 (4)
C60.24513 (19)1.05051 (19)0.58226 (15)0.0304 (4)
C70.1567 (2)1.1973 (2)0.52203 (17)0.0344 (4)
C80.0817 (2)1.2353 (2)0.41798 (17)0.0384 (4)
C90.0887 (2)1.1298 (2)0.37306 (19)0.0431 (5)
C100.1752 (2)0.9826 (2)0.43219 (18)0.0398 (4)
C110.2554 (2)0.9424 (2)0.53481 (16)0.0341 (4)
O120.34923 (17)0.80024 (14)0.59518 (12)0.0422 (3)
C130.3730 (3)0.6863 (2)0.5458 (2)0.0463 (5)
C140.4946 (2)0.5453 (2)0.62109 (19)0.0414 (5)
C150.4567 (2)0.4404 (2)0.6931 (2)0.0433 (5)
C160.5679 (3)0.3085 (3)0.7622 (2)0.0524 (6)
C170.7178 (3)0.2813 (3)0.7578 (3)0.0599 (7)
C180.7579 (3)0.3847 (3)0.6866 (3)0.0650 (8)
C190.6469 (3)0.5170 (3)0.6178 (2)0.0533 (6)
C200.2847 (2)1.1372 (2)0.73542 (16)0.0350 (4)
N210.2518 (2)1.23812 (19)0.76384 (17)0.0481 (4)
C220.1827 (2)0.90207 (19)0.82009 (15)0.0316 (4)
O230.07083 (15)1.02139 (14)0.78492 (13)0.0446 (4)
C240.1688 (2)0.7713 (2)0.89974 (15)0.0325 (4)
C250.0677 (3)0.7920 (3)0.9841 (2)0.0472 (5)
C260.0475 (3)0.6741 (3)1.0559 (2)0.0579 (6)
C270.1249 (3)0.5373 (3)1.0421 (2)0.0537 (6)
C280.2208 (3)0.5165 (2)0.9567 (2)0.0509 (5)
C290.2441 (2)0.6330 (2)0.88615 (19)0.0410 (4)
H10.356 (3)0.458 (2)0.6938 (19)0.038 (6)*
H20.143 (3)1.273 (3)0.555 (2)0.045 (6)*
H30.497 (2)0.687 (2)0.7912 (17)0.028 (5)*
H40.544 (2)1.021 (3)0.6607 (19)0.039 (6)*
H50.679 (3)0.757 (3)0.787 (2)0.049 (6)*
H60.474 (3)0.721 (2)0.907 (2)0.040 (6)*
H70.533 (2)0.896 (2)0.6244 (19)0.037 (5)*
H80.011 (3)0.888 (3)0.984 (2)0.058 (7)*
H90.668 (3)0.589 (3)0.566 (2)0.063 (8)*
H100.305 (3)0.619 (2)0.8272 (19)0.037 (6)*
H110.104 (3)0.461 (3)1.088 (2)0.068 (8)*
H120.793 (3)0.196 (3)0.804 (3)0.068 (8)*
H130.270 (3)0.682 (3)0.539 (2)0.049 (6)*
H140.182 (3)0.916 (3)0.403 (2)0.048 (7)*
H150.266 (3)0.425 (3)0.942 (2)0.068 (8)*
H160.542 (3)0.239 (3)0.815 (2)0.063 (8)*
H170.407 (3)0.715 (3)0.469 (2)0.052 (7)*
H18−0.018 (3)0.690 (3)1.108 (3)0.071 (9)*
H190.035 (3)1.158 (3)0.306 (2)0.051 (7)*
H200.851 (4)0.373 (3)0.681 (3)0.077 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl310.0534 (3)0.0406 (3)0.0619 (4)−0.0149 (2)−0.0160 (3)0.0080 (2)
Cl300.0710 (4)0.0549 (3)0.0636 (4)−0.0323 (3)−0.0220 (3)−0.0077 (3)
C10.0280 (8)0.0250 (8)0.0329 (9)−0.0100 (6)0.0045 (7)−0.0088 (7)
N20.0265 (7)0.0229 (6)0.0323 (7)−0.0076 (5)0.0022 (6)−0.0055 (6)
C30.0290 (9)0.0270 (8)0.0430 (11)−0.0061 (7)−0.0027 (8)−0.0065 (8)
C40.0292 (9)0.0368 (10)0.0516 (12)−0.0097 (8)−0.0020 (8)−0.0111 (9)
C50.0282 (9)0.0382 (10)0.0442 (11)−0.0127 (8)0.0065 (8)−0.0110 (9)
C60.0277 (8)0.0278 (8)0.0325 (9)−0.0105 (7)0.0051 (7)−0.0084 (7)
C70.0305 (9)0.0283 (9)0.0389 (10)−0.0116 (7)0.0036 (7)−0.0054 (7)
C80.0307 (9)0.0323 (9)0.0417 (10)−0.0115 (7)−0.0008 (8)−0.0003 (8)
C90.0356 (10)0.0510 (12)0.0386 (11)−0.0195 (9)−0.0018 (8)−0.0069 (9)
C100.0399 (10)0.0414 (10)0.0400 (10)−0.0187 (9)0.0039 (8)−0.0142 (9)
C110.0326 (9)0.0315 (9)0.0352 (9)−0.0118 (7)0.0064 (7)−0.0110 (7)
O120.0503 (8)0.0267 (6)0.0417 (8)−0.0060 (6)−0.0035 (6)−0.0155 (6)
C130.0565 (13)0.0316 (10)0.0500 (13)−0.0131 (9)0.0006 (10)−0.0207 (9)
C140.0409 (10)0.0326 (9)0.0527 (12)−0.0102 (8)0.0025 (9)−0.0249 (9)
C150.0390 (11)0.0368 (10)0.0538 (12)−0.0117 (8)0.0042 (9)−0.0216 (9)
C160.0558 (13)0.0375 (11)0.0572 (14)−0.0129 (10)−0.0011 (11)−0.0164 (10)
C170.0494 (13)0.0444 (13)0.0717 (17)−0.0015 (11)−0.0134 (12)−0.0244 (12)
C180.0349 (12)0.0729 (18)0.094 (2)−0.0149 (12)0.0007 (12)−0.0468 (17)
C190.0502 (13)0.0527 (13)0.0699 (16)−0.0275 (11)0.0123 (11)−0.0304 (12)
C200.0355 (9)0.0285 (9)0.0378 (10)−0.0133 (7)0.0027 (7)−0.0074 (7)
N210.0558 (11)0.0355 (9)0.0549 (11)−0.0203 (8)0.0063 (9)−0.0169 (8)
C220.0313 (8)0.0284 (8)0.0341 (9)−0.0115 (7)0.0056 (7)−0.0117 (7)
O230.0309 (7)0.0294 (7)0.0593 (9)−0.0059 (5)0.0102 (6)−0.0081 (6)
C240.0332 (9)0.0323 (9)0.0320 (9)−0.0153 (7)0.0018 (7)−0.0086 (7)
C250.0523 (12)0.0499 (12)0.0497 (12)−0.0291 (11)0.0201 (10)−0.0229 (10)
C260.0654 (15)0.0761 (17)0.0443 (13)−0.0452 (14)0.0204 (12)−0.0171 (12)
C270.0549 (13)0.0520 (13)0.0500 (13)−0.0336 (11)−0.0065 (10)0.0076 (10)
C280.0491 (12)0.0346 (11)0.0648 (15)−0.0206 (10)−0.0013 (11)−0.0054 (10)
C290.0418 (10)0.0345 (10)0.0455 (11)−0.0163 (8)0.0070 (9)−0.0128 (8)
Geometric parameters (Å, º) top
Cl31—C81.735 (2)C13—H131.04 (3)
Cl30—C41.791 (2)C13—H170.99 (3)
C1—N21.474 (2)C14—C151.374 (3)
C1—C201.491 (2)C14—C191.386 (3)
C1—C61.524 (3)C15—C161.391 (3)
C1—C51.552 (2)C15—H10.92 (2)
N2—C221.358 (2)C16—C171.366 (4)
N2—C31.473 (2)C16—H160.94 (3)
C3—C41.510 (3)C17—C181.371 (4)
C3—H30.97 (2)C17—H120.92 (3)
C3—H60.92 (2)C18—C191.391 (4)
C4—C51.518 (3)C18—H200.86 (3)
C4—H50.94 (2)C19—H90.93 (3)
C5—H40.96 (2)C20—N211.137 (3)
C5—H70.96 (2)C22—O231.226 (2)
C6—C71.389 (3)C22—C241.495 (3)
C6—C111.408 (3)C24—C291.384 (3)
C7—C81.383 (3)C24—C251.384 (3)
C7—H20.97 (2)C25—C261.384 (3)
C8—C91.373 (3)C25—H80.93 (3)
C9—C101.387 (3)C26—C271.372 (4)
C9—H190.91 (3)C26—H180.88 (3)
C10—C111.388 (3)C27—C281.364 (4)
C10—H140.87 (3)C27—H110.93 (3)
C11—O121.367 (2)C28—C291.382 (3)
O12—C131.444 (2)C28—H150.95 (3)
C13—C141.503 (3)C29—H100.91 (2)
N2—C1—C20109.20 (14)O12—C13—C14106.96 (17)
N2—C1—C6114.02 (14)O12—C13—H13109.4 (13)
C20—C1—C6109.83 (14)C14—C13—H13113.1 (13)
N2—C1—C5102.64 (14)O12—C13—H17106.6 (14)
C20—C1—C5108.75 (16)C14—C13—H17111.2 (14)
C6—C1—C5112.09 (15)H13—C13—H17109 (2)
C22—N2—C3128.35 (15)C15—C14—C19118.7 (2)
C22—N2—C1119.22 (14)C15—C14—C13120.3 (2)
C3—N2—C1112.36 (14)C19—C14—C13121.0 (2)
N2—C3—C4103.58 (15)C14—C15—C16121.2 (2)
N2—C3—H3110.8 (12)C14—C15—H1119.0 (14)
C4—C3—H3107.1 (12)C16—C15—H1119.9 (14)
N2—C3—H6110.3 (14)C17—C16—C15119.7 (3)
C4—C3—H6113.4 (14)C17—C16—H16118.8 (17)
H3—C3—H6111.4 (18)C15—C16—H16121.5 (17)
C3—C4—C5103.64 (16)C16—C17—C18120.0 (2)
C3—C4—Cl30111.10 (16)C16—C17—H12121.4 (18)
C5—C4—Cl30111.88 (15)C18—C17—H12118.6 (18)
C3—C4—H5111.3 (15)C17—C18—C19120.4 (2)
C5—C4—H5112.2 (15)C17—C18—H20124 (2)
Cl30—C4—H5106.8 (15)C19—C18—H20116 (2)
C4—C5—C1105.15 (16)C14—C19—C18120.1 (3)
C4—C5—H4113.8 (13)C14—C19—H9115.8 (17)
C1—C5—H4112.5 (13)C18—C19—H9124.1 (17)
C4—C5—H7106.9 (13)N21—C20—C1176.5 (2)
C1—C5—H7108.0 (13)O23—C22—N2120.07 (17)
H4—C5—H7110.1 (19)O23—C22—C24121.38 (17)
C7—C6—C11118.25 (17)N2—C22—C24118.54 (15)
C7—C6—C1121.17 (16)C29—C24—C25118.98 (19)
C11—C6—C1120.52 (15)C29—C24—C22122.17 (17)
C8—C7—C6120.49 (18)C25—C24—C22118.63 (17)
C8—C7—H2120.0 (14)C24—C25—C26120.0 (2)
C6—C7—H2119.5 (14)C24—C25—H8115.9 (16)
C9—C8—C7121.24 (18)C26—C25—H8123.9 (16)
C9—C8—Cl31120.22 (16)C27—C26—C25120.2 (2)
C7—C8—Cl31118.54 (16)C27—C26—H18121.2 (19)
C8—C9—C10119.2 (2)C25—C26—H18118.6 (19)
C8—C9—H19119.1 (15)C28—C27—C26120.5 (2)
C10—C9—H19121.6 (16)C28—C27—H11120.9 (18)
C9—C10—C11120.3 (2)C26—C27—H11118.4 (18)
C9—C10—H14119.2 (16)C27—C28—C29119.7 (2)
C11—C10—H14120.4 (16)C27—C28—H15120.7 (18)
O12—C11—C10123.82 (17)C29—C28—H15119.3 (18)
O12—C11—C6115.78 (16)C28—C29—C24120.6 (2)
C10—C11—C6120.39 (17)C28—C29—H10118.8 (14)
C11—O12—C13117.91 (16)C24—C29—H10120.4 (14)
C20—C1—N2—C2264.0 (2)C7—C6—C11—C10−1.9 (3)
C6—C1—N2—C22−59.3 (2)C1—C6—C11—C10−179.10 (17)
C5—C1—N2—C22179.22 (16)C10—C11—O12—C133.8 (3)
C20—C1—N2—C3−113.25 (17)C6—C11—O12—C13−175.28 (18)
C6—C1—N2—C3123.48 (16)C11—O12—C13—C14172.84 (18)
C5—C1—N2—C32.02 (19)O12—C13—C14—C15105.1 (2)
C22—N2—C3—C4−157.32 (18)O12—C13—C14—C19−76.2 (3)
C1—N2—C3—C419.6 (2)C19—C14—C15—C160.4 (3)
N2—C3—C4—C5−33.1 (2)C13—C14—C15—C16179.1 (2)
N2—C3—C4—Cl3087.23 (17)C14—C15—C16—C17−0.8 (3)
C3—C4—C5—C135.1 (2)C15—C16—C17—C180.9 (4)
Cl30—C4—C5—C1−84.71 (17)C16—C17—C18—C19−0.6 (4)
N2—C1—C5—C4−22.87 (19)C15—C14—C19—C18−0.1 (3)
C20—C1—C5—C492.73 (19)C13—C14—C19—C18−178.8 (2)
C6—C1—C5—C4−145.63 (16)C17—C18—C19—C140.2 (4)
N2—C1—C6—C7135.27 (17)C3—N2—C22—O23169.57 (18)
C20—C1—C6—C712.3 (2)C1—N2—C22—O23−7.1 (3)
C5—C1—C6—C7−108.67 (19)C3—N2—C22—C24−11.9 (3)
N2—C1—C6—C11−47.6 (2)C1—N2—C22—C24171.39 (15)
C20—C1—C6—C11−170.52 (16)O23—C22—C24—C29136.3 (2)
C5—C1—C6—C1168.5 (2)N2—C22—C24—C29−42.2 (3)
C11—C6—C7—C8−0.3 (3)O23—C22—C24—C25−38.3 (3)
C1—C6—C7—C8176.90 (17)N2—C22—C24—C25143.23 (19)
C6—C7—C8—C91.9 (3)C29—C24—C25—C262.4 (3)
C6—C7—C8—Cl31−178.36 (14)C22—C24—C25—C26177.2 (2)
C7—C8—C9—C10−1.3 (3)C24—C25—C26—C27−1.5 (4)
Cl31—C8—C9—C10178.97 (16)C25—C26—C27—C28−0.9 (4)
C8—C9—C10—C11−0.9 (3)C26—C27—C28—C292.3 (4)
C9—C10—C11—O12−176.54 (19)C27—C28—C29—C24−1.3 (3)
C9—C10—C11—C62.5 (3)C25—C24—C29—C28−1.0 (3)
C7—C6—C11—O12177.23 (16)C22—C24—C29—C28−175.61 (19)
C1—C6—C11—O120.0 (2)

Experimental details

Crystal data
Chemical formulaC25H20Cl2N2O2
Mr451.33
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.803 (2), 10.653 (2), 12.364 (3)
α, β, γ (°)72.12 (3), 85.82 (3), 63.71 (3)
V (Å3)1098.7 (5)
Z2
Radiation typeMo Kα
µ (mm−1)0.32
Crystal size (mm)0.35 × 0.28 × 0.22
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		5515, 5275, 4051
Rint0.022
(sin θ/λ)max (Å−1)0.660
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.131, 1.03
No. of reflections5275
No. of parameters360
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.29, −0.50

Computer programs: CAD-4 (Enraf–Nonius, 1988), HELENA (Meetsma & Spek, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).

 

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