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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Benzyl 2-{4-[2-(4-chloro­benzoyl­amino)­eth­yl]phen­­oxy}-2-methyl­propionate

aDepartment of Chemistry, University of Gujrat, Gujrat, Pakistan, bMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and cX-ray Diffraction and Crystallography Laboratory, Department of Physics, School of Physical Sciences, University of the Punjab, Quaid-e-Azam Campus, Lahore 54590, Pakistan
*Correspondence e-mail: ghulam.mustafa@uog.edu.pk

(Received 20 September 2011; accepted 24 September 2011; online 30 September 2011)

In the title compound, C26H26ClNO4, the central phenyl­ene ring is oriented at dihedral angles of 5.06 (14) and 64.14 (5)°, respectively, with respect to aromatic rings of the benzyl and chloro­phenyl groups. The centroid–centroid distance between the central phenyl­ene ring and the aromatic ring of the benzyl group is 4.028 (12) Å. In the crystal, inter­molecular N—H⋯O hydrogen bond generate a chain along (100). C—H⋯O inter­actions are also observed.

Related literature

For background to the drug bezafibrate [systematic name: 2-(4-{2-[(4-chloro­benzo­yl)amino]­eth­yl}phen­oxy)-2-methyl­prop­anoic acid], commonly used against hyperlipidemia, which has been found to decrease mRNA levels in adipocyte markers and increase fatty acid oxidation in primary cultures of adipocytes, see: Cabrero et al. (2001[Cabrero, A., Alegret, M., Sanchez, R. M., Adzet, T., Laguna, J. C. & Vazquez, M. (2001). Diabetes, 50, 1883-1890.]).

[Scheme 1]

Experimental

Crystal data
  • C26H26ClNO4

  • Mr = 451.93

  • Triclinic, [P \overline 1]

  • a = 5.5480 (1) Å

  • b = 11.0716 (3) Å

  • c = 18.9641 (5) Å

  • α = 82.247 (1)°

  • β = 86.915 (1)°

  • γ = 85.674 (1)°

  • V = 1149.81 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 296 K

  • 0.41 × 0.19 × 0.13 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.923, Tmax = 0.975

  • 26646 measured reflections

  • 5750 independent reflections

  • 4355 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.142

  • S = 1.05

  • 5745 reflections

  • 294 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O4i 0.848 (19) 2.540 (19) 3.350 (2) 160.3 (18)
C17—H17B⋯O4ii 0.97 2.57 3.532 (3) 172
C7—H7B⋯O2i 0.97 2.59 3.398 (3) 141
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Among the fibrate family of drugs bezafibrate (2-(4-{2-[(4-chlorobenzoyl)amino]ethyl}phenoxy)-2-methylpropanoic acid) is well known for its use against hyperlipidemia. The drug has also found effective in decreases of mRNA levels in adipocyte markers and increases fatty acid oxidation in primary culture of adipocytes (Cabrero et al., 2001). Here in, we report the crystal structure of benzyl ester of bezafibrate (I).

The crysral structure of title compound consist of three aromatic rings. The aromatic ring (C1—C6) is oriented at dihedral angle of 5.06 (14)° with respect to other ring (C10—C15) and the centroid distance between these two rings is 4.028 Å. The chloro benzene ring (C19—C24) is twisted at dihedral angle of 64.14 (5)° with respect to the ring (C10—C15). The molecule is connected through only intermolecular hydrogen bonding of N—H···O and C—H···O type and generate an infinite chain along base vector (1 0 0).

Related literature top

For background to the drug bezafibrate [2-(4-{2-[(4-chlorobenzoyl)amino]ethyl}phenoxy)-2-methylpropanoic acid], commonly used against hyperlipidemia, which has been found to decrease mRNA levels in adipocyte markers and increase fatty acid oxidation in primary cultures of adipocytes, see: Cabrero et al. (2001)

Experimental top

A weighed amount of bezafibrate (0.40 g, 0.001105 moles) was dissolved in DMF (10 cm3) taken in a 100 ml conical flask. Then sodium hydride (0.0530 g; 0.002210 moles) washed with n-hexane was added in reaction flask. The reaction mixture was stirred for about 1 hr at an ambient temperature until the NaH disappeared. An equivalent amount of benzyl chloride (0.14 g, 0.001105 moles) was then added in the reaction mixture and stirred until the solution became clear. The reaction was monitored after regular intervals by TLC. After the consumption of benzyl chloride, the reaction mixture was poured over the crushed ice. The crude precipitates were filtered, washed with distilled water and crystallized with methanol to get colorless crystals. Melting point of product was noted as 374K.

Refinement top

All the C—H and H-atoms were positioned with idealized geometry with Caromatic—H = 0.93 Å, Cmethylene—H = 0.97 Å & Cmethyl—H = 0.96 Å and were refined using a riding model with Uiso(H) = 1.2 Ueq(C) for aromatic & methylene similarly Uiso(H) = 1.5 Ueq(C) for methyl carbon atoms. The N—H H-atom was refined via difference map. The reflections (0 0 1), (0 -1 1), (0 1 1), (0 1 0) and (0 0 2) have been omitted in final refinement.

Structure description top

Among the fibrate family of drugs bezafibrate (2-(4-{2-[(4-chlorobenzoyl)amino]ethyl}phenoxy)-2-methylpropanoic acid) is well known for its use against hyperlipidemia. The drug has also found effective in decreases of mRNA levels in adipocyte markers and increases fatty acid oxidation in primary culture of adipocytes (Cabrero et al., 2001). Here in, we report the crystal structure of benzyl ester of bezafibrate (I).

The crysral structure of title compound consist of three aromatic rings. The aromatic ring (C1—C6) is oriented at dihedral angle of 5.06 (14)° with respect to other ring (C10—C15) and the centroid distance between these two rings is 4.028 Å. The chloro benzene ring (C19—C24) is twisted at dihedral angle of 64.14 (5)° with respect to the ring (C10—C15). The molecule is connected through only intermolecular hydrogen bonding of N—H···O and C—H···O type and generate an infinite chain along base vector (1 0 0).

For background to the drug bezafibrate [2-(4-{2-[(4-chlorobenzoyl)amino]ethyl}phenoxy)-2-methylpropanoic acid], commonly used against hyperlipidemia, which has been found to decrease mRNA levels in adipocyte markers and increase fatty acid oxidation in primary cultures of adipocytes, see: Cabrero et al. (2001)

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The ORTEP diagram of (I) showing the thermal ellipsoids drawn at 50% probability level.
[Figure 2] Fig. 2. Unit cell diagram showing the N—H···O & C—H···O type interactions using dashed lines.
Benzyl 2-{4-[2-(4-chlorobenzoylamino)ethyl]phenoxy}-2-methylpropionate top
Crystal data top
C26H26ClNO4Z = 2
Mr = 451.93F(000) = 476
Triclinic, P1Dx = 1.305 Mg m3
Hall symbol: -P 1Melting point: 374 K
a = 5.5480 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.0716 (3) ÅCell parameters from 9981 reflections
c = 18.9641 (5) Åθ = 2.3–28.3°
α = 82.247 (1)°µ = 0.20 mm1
β = 86.915 (1)°T = 296 K
γ = 85.674 (1)°Needle, colorless
V = 1149.81 (5) Å30.41 × 0.19 × 0.13 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5750 independent reflections
Radiation source: fine-focus sealed tube4355 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 28.4°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 77
Tmin = 0.923, Tmax = 0.975k = 1414
26646 measured reflectionsl = 2525
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.061P)2 + 0.3442P]
where P = (Fo2 + 2Fc2)/3
5745 reflections(Δ/σ)max = 0.001
294 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C26H26ClNO4γ = 85.674 (1)°
Mr = 451.93V = 1149.81 (5) Å3
Triclinic, P1Z = 2
a = 5.5480 (1) ÅMo Kα radiation
b = 11.0716 (3) ŵ = 0.20 mm1
c = 18.9641 (5) ÅT = 296 K
α = 82.247 (1)°0.41 × 0.19 × 0.13 mm
β = 86.915 (1)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5750 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
4355 reflections with I > 2σ(I)
Tmin = 0.923, Tmax = 0.975Rint = 0.019
26646 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.23 e Å3
5745 reflectionsΔρmin = 0.30 e Å3
294 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl10.38362 (13)0.18807 (5)0.70547 (3)0.0904 (2)
O30.10285 (18)0.90785 (9)0.18989 (5)0.0445 (3)
O10.0350 (2)0.78925 (10)0.07992 (6)0.0496 (3)
C100.1251 (2)0.79595 (13)0.23181 (7)0.0384 (3)
C190.4577 (3)0.15357 (13)0.55164 (7)0.0396 (3)
C110.0609 (3)0.77345 (14)0.28206 (8)0.0421 (3)
H110.18780.83240.28600.051*
C220.4136 (3)0.05599 (14)0.64589 (9)0.0499 (4)
C130.1266 (3)0.57405 (15)0.32228 (8)0.0487 (4)
C200.6232 (3)0.12007 (15)0.60402 (8)0.0478 (4)
H200.75080.16870.60720.057*
C80.2515 (3)0.83311 (14)0.07877 (8)0.0463 (3)
C240.2680 (3)0.08072 (14)0.54764 (8)0.0476 (4)
H240.15440.10330.51310.057*
C120.0594 (3)0.66391 (15)0.32648 (8)0.0482 (4)
H120.18620.65010.36000.058*
C90.2523 (3)0.93371 (14)0.12628 (8)0.0437 (3)
C230.2462 (3)0.02508 (15)0.59448 (9)0.0512 (4)
H230.12020.07470.59130.061*
N10.3016 (3)0.32670 (14)0.47282 (8)0.0598 (4)
C140.3122 (3)0.59869 (16)0.27238 (9)0.0556 (4)
H140.43980.54010.26880.067*
O20.4214 (2)0.80229 (15)0.04190 (8)0.0763 (4)
C210.6010 (3)0.01526 (16)0.65165 (9)0.0541 (4)
H210.71160.00660.68710.065*
C160.1268 (4)0.45288 (17)0.37026 (10)0.0617 (5)
H16A0.03090.44540.39450.074*
H16B0.15430.38700.34130.074*
C150.3146 (3)0.70842 (16)0.22724 (9)0.0520 (4)
H150.44260.72290.19420.062*
C10.0495 (3)0.56932 (15)0.08517 (9)0.0502 (4)
C250.1281 (3)1.04863 (15)0.08638 (10)0.0559 (4)
H25A0.11441.11260.11620.084*
H25B0.03031.03140.07420.084*
H25C0.22211.07410.04370.084*
C70.0082 (4)0.68946 (16)0.03881 (10)0.0602 (4)
H7A0.12400.69410.00150.072*
H7B0.15320.69620.02070.072*
C260.5075 (3)0.9593 (2)0.14196 (11)0.0680 (5)
H26A0.58980.88560.16410.102*
H26B0.50111.02060.17340.102*
H26C0.59320.98780.09830.102*
C170.3137 (4)0.44022 (18)0.42382 (11)0.0737 (6)
H17A0.47230.44200.39970.088*
H17B0.29290.50900.45080.088*
C20.2552 (4)0.4958 (2)0.07900 (14)0.0793 (6)
H20.37590.51920.04510.095*
C60.1203 (4)0.5317 (2)0.13600 (15)0.0838 (7)
H60.26260.58050.14100.101*
C40.1144 (5)0.35045 (19)0.17350 (14)0.0811 (7)
H40.13530.27670.20320.097*
C30.2855 (5)0.3846 (2)0.12373 (17)0.0952 (8)
H30.42550.33410.11880.114*
C50.0874 (6)0.4237 (2)0.18012 (16)0.0991 (9)
H50.20590.40090.21490.119*
O40.7030 (2)0.29952 (12)0.48642 (7)0.0642 (3)
C180.4982 (3)0.26677 (14)0.50064 (8)0.0465 (3)
H1N0.159 (3)0.3084 (18)0.4862 (10)0.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1179 (5)0.0585 (3)0.0845 (4)0.0129 (3)0.0086 (3)0.0335 (3)
O30.0462 (6)0.0410 (5)0.0416 (5)0.0000 (4)0.0017 (4)0.0081 (4)
O10.0492 (6)0.0451 (6)0.0538 (6)0.0078 (5)0.0060 (5)0.0003 (5)
C100.0392 (7)0.0409 (7)0.0330 (6)0.0035 (5)0.0046 (5)0.0041 (5)
C190.0465 (7)0.0357 (7)0.0350 (7)0.0017 (6)0.0001 (6)0.0001 (5)
C110.0394 (7)0.0473 (8)0.0378 (7)0.0005 (6)0.0011 (5)0.0013 (6)
C220.0610 (9)0.0367 (7)0.0474 (8)0.0015 (7)0.0019 (7)0.0073 (6)
C130.0527 (8)0.0486 (8)0.0412 (8)0.0060 (7)0.0074 (6)0.0104 (6)
C200.0461 (8)0.0511 (9)0.0450 (8)0.0073 (6)0.0056 (6)0.0018 (7)
C80.0447 (8)0.0491 (8)0.0404 (8)0.0036 (6)0.0003 (6)0.0108 (6)
C240.0531 (8)0.0445 (8)0.0447 (8)0.0053 (6)0.0119 (7)0.0011 (6)
C120.0453 (8)0.0583 (9)0.0380 (7)0.0092 (7)0.0024 (6)0.0064 (7)
C90.0399 (7)0.0464 (8)0.0413 (7)0.0101 (6)0.0029 (6)0.0110 (6)
C230.0556 (9)0.0428 (8)0.0548 (9)0.0110 (7)0.0031 (7)0.0008 (7)
N10.0678 (9)0.0487 (8)0.0573 (9)0.0077 (7)0.0119 (7)0.0189 (7)
C140.0535 (9)0.0530 (9)0.0522 (9)0.0118 (7)0.0016 (7)0.0120 (7)
O20.0602 (8)0.0969 (11)0.0716 (9)0.0088 (7)0.0190 (7)0.0172 (8)
C210.0533 (9)0.0581 (10)0.0465 (9)0.0024 (7)0.0090 (7)0.0080 (7)
C160.0690 (11)0.0530 (10)0.0578 (10)0.0112 (8)0.0102 (8)0.0185 (8)
C150.0445 (8)0.0582 (10)0.0451 (8)0.0065 (7)0.0081 (6)0.0133 (7)
C10.0567 (9)0.0442 (8)0.0513 (9)0.0047 (7)0.0084 (7)0.0088 (7)
C250.0633 (10)0.0434 (8)0.0568 (10)0.0116 (7)0.0070 (8)0.0155 (7)
C70.0758 (12)0.0519 (10)0.0539 (10)0.0084 (8)0.0143 (9)0.0038 (8)
C260.0477 (9)0.0863 (14)0.0692 (12)0.0240 (9)0.0087 (8)0.0061 (10)
C170.1014 (16)0.0500 (10)0.0662 (12)0.0202 (10)0.0312 (11)0.0239 (9)
C20.0739 (13)0.0740 (14)0.0859 (15)0.0102 (11)0.0138 (11)0.0106 (12)
C60.0694 (13)0.0593 (12)0.1124 (19)0.0032 (10)0.0217 (13)0.0117 (12)
C40.1112 (19)0.0473 (11)0.0844 (16)0.0056 (11)0.0249 (14)0.0003 (10)
C30.0857 (17)0.0709 (15)0.127 (2)0.0317 (13)0.0177 (16)0.0201 (15)
C50.112 (2)0.0640 (14)0.111 (2)0.0102 (14)0.0267 (16)0.0167 (13)
O40.0664 (8)0.0601 (8)0.0629 (8)0.0201 (6)0.0008 (6)0.0118 (6)
C180.0619 (9)0.0400 (8)0.0369 (7)0.0088 (7)0.0034 (6)0.0011 (6)
Geometric parameters (Å, º) top
Cl1—C221.7359 (16)C14—C151.389 (2)
O3—C101.3798 (16)C14—H140.9300
O3—C91.4353 (17)C21—H210.9300
O1—C81.3273 (19)C16—C171.476 (3)
O1—C71.456 (2)C16—H16A0.9700
C10—C111.380 (2)C16—H16B0.9700
C10—C151.382 (2)C15—H150.9300
C19—C201.384 (2)C1—C61.358 (3)
C19—C241.385 (2)C1—C21.360 (3)
C19—C181.4996 (19)C1—C71.502 (2)
C11—C121.380 (2)C25—H25A0.9600
C11—H110.9300C25—H25B0.9600
C22—C211.369 (2)C25—H25C0.9600
C22—C231.375 (2)C7—H7A0.9700
C13—C141.378 (2)C7—H7B0.9700
C13—C121.385 (2)C26—H26A0.9600
C13—C161.516 (2)C26—H26B0.9600
C20—C211.380 (2)C26—H26C0.9600
C20—H200.9300C17—H17A0.9700
C8—O21.199 (2)C17—H17B0.9700
C8—C91.525 (2)C2—C31.402 (3)
C24—C231.380 (2)C2—H20.9300
C24—H240.9300C6—C51.370 (3)
C12—H120.9300C6—H60.9300
C9—C261.517 (2)C4—C31.340 (4)
C9—C251.527 (2)C4—C51.343 (4)
C23—H230.9300C4—H40.9300
N1—C181.329 (2)C3—H30.9300
N1—C171.462 (2)C5—H50.9300
N1—H1N0.848 (19)O4—C181.224 (2)
C10—O3—C9121.21 (11)C13—C16—H16B109.1
C8—O1—C7117.82 (14)H16A—C16—H16B107.8
O3—C10—C11115.14 (12)C10—C15—C14119.48 (14)
O3—C10—C15125.57 (13)C10—C15—H15120.3
C11—C10—C15119.29 (13)C14—C15—H15120.3
C20—C19—C24119.15 (13)C6—C1—C2117.80 (19)
C20—C19—C18117.50 (13)C6—C1—C7119.92 (17)
C24—C19—C18123.33 (13)C2—C1—C7122.28 (18)
C10—C11—C12120.27 (14)C9—C25—H25A109.5
C10—C11—H11119.9C9—C25—H25B109.5
C12—C11—H11119.9H25A—C25—H25B109.5
C21—C22—C23121.71 (14)C9—C25—H25C109.5
C21—C22—Cl1119.41 (13)H25A—C25—H25C109.5
C23—C22—Cl1118.87 (13)H25B—C25—H25C109.5
C14—C13—C12117.37 (14)O1—C7—C1109.73 (14)
C14—C13—C16120.99 (15)O1—C7—H7A109.7
C12—C13—C16121.64 (15)C1—C7—H7A109.7
C21—C20—C19120.70 (15)O1—C7—H7B109.7
C21—C20—H20119.6C1—C7—H7B109.7
C19—C20—H20119.6H7A—C7—H7B108.2
O2—C8—O1124.18 (17)C9—C26—H26A109.5
O2—C8—C9124.20 (15)C9—C26—H26B109.5
O1—C8—C9111.50 (13)H26A—C26—H26B109.5
C23—C24—C19120.52 (14)C9—C26—H26C109.5
C23—C24—H24119.7H26A—C26—H26C109.5
C19—C24—H24119.7H26B—C26—H26C109.5
C11—C12—C13121.54 (14)N1—C17—C16112.07 (16)
C11—C12—H12119.2N1—C17—H17A109.2
C13—C12—H12119.2C16—C17—H17A109.2
O3—C9—C26112.45 (13)N1—C17—H17B109.2
O3—C9—C8111.48 (11)C16—C17—H17B109.2
C26—C9—C8111.72 (15)H17A—C17—H17B107.9
O3—C9—C25104.40 (13)C1—C2—C3120.1 (2)
C26—C9—C25109.32 (14)C1—C2—H2120.0
C8—C9—C25107.05 (13)C3—C2—H2120.0
C22—C23—C24118.96 (15)C1—C6—C5121.6 (2)
C22—C23—H23120.5C1—C6—H6119.2
C24—C23—H23120.5C5—C6—H6119.2
C18—N1—C17122.04 (17)C3—C4—C5119.4 (2)
C18—N1—H1N123.1 (13)C3—C4—H4120.3
C17—N1—H1N114.4 (13)C5—C4—H4120.3
C13—C14—C15122.03 (15)C4—C3—C2120.6 (2)
C13—C14—H14119.0C4—C3—H3119.7
C15—C14—H14119.0C2—C3—H3119.7
C22—C21—C20118.94 (15)C4—C5—C6120.6 (2)
C22—C21—H21120.5C4—C5—H5119.7
C20—C21—H21120.5C6—C5—H5119.7
C17—C16—C13112.54 (15)O4—C18—N1123.41 (15)
C17—C16—H16A109.1O4—C18—C19120.39 (14)
C13—C16—H16A109.1N1—C18—C19116.19 (14)
C17—C16—H16B109.1
C9—O3—C10—C11166.62 (13)C23—C22—C21—C200.7 (3)
C9—O3—C10—C1513.7 (2)Cl1—C22—C21—C20179.99 (13)
O3—C10—C11—C12179.26 (13)C19—C20—C21—C220.6 (3)
C15—C10—C11—C121.0 (2)C14—C13—C16—C1770.4 (3)
C24—C19—C20—C210.3 (2)C12—C13—C16—C17109.8 (2)
C18—C19—C20—C21178.30 (15)O3—C10—C15—C14179.17 (15)
C7—O1—C8—O25.9 (2)C11—C10—C15—C141.1 (2)
C7—O1—C8—C9178.00 (12)C13—C14—C15—C100.4 (3)
C20—C19—C24—C231.1 (2)C8—O1—C7—C192.40 (18)
C18—C19—C24—C23177.38 (15)C6—C1—C7—O173.1 (2)
C10—C11—C12—C130.1 (2)C2—C1—C7—O1106.0 (2)
C14—C13—C12—C110.7 (2)C18—N1—C17—C16147.0 (2)
C16—C13—C12—C11179.06 (15)C13—C16—C17—N1176.16 (18)
C10—O3—C9—C2676.41 (18)C6—C1—C2—C30.7 (3)
C10—O3—C9—C849.95 (16)C7—C1—C2—C3179.8 (2)
C10—O3—C9—C25165.19 (12)C2—C1—C6—C50.2 (4)
O2—C8—C9—O3146.77 (16)C7—C1—C6—C5178.9 (2)
O1—C8—C9—O337.15 (16)C5—C4—C3—C20.2 (4)
O2—C8—C9—C2620.0 (2)C1—C2—C3—C40.9 (4)
O1—C8—C9—C26163.91 (13)C3—C4—C5—C60.8 (4)
O2—C8—C9—C2599.64 (18)C1—C6—C5—C41.0 (5)
O1—C8—C9—C2576.44 (15)C17—N1—C18—O41.8 (3)
C21—C22—C23—C240.1 (3)C17—N1—C18—C19178.35 (16)
Cl1—C22—C23—C24179.17 (13)C20—C19—C18—O428.4 (2)
C19—C24—C23—C221.0 (3)C24—C19—C18—O4150.07 (16)
C12—C13—C14—C150.5 (3)C20—C19—C18—N1151.74 (16)
C16—C13—C14—C15179.19 (17)C24—C19—C18—N129.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O4i0.848 (19)2.540 (19)3.350 (2)160.3 (18)
C17—H17B···O4ii0.972.573.532 (3)172
C7—H7B···O2i0.972.593.398 (3)141
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC26H26ClNO4
Mr451.93
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)5.5480 (1), 11.0716 (3), 18.9641 (5)
α, β, γ (°)82.247 (1), 86.915 (1), 85.674 (1)
V3)1149.81 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.41 × 0.19 × 0.13
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.923, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
26646, 5750, 4355
Rint0.019
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.142, 1.05
No. of reflections5745
No. of parameters294
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.30

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O4i0.848 (19)2.540 (19)3.350 (2)160.3 (18)
C17—H17B···O4ii0.972.573.532 (3)171.7
C7—H7B···O2i0.972.593.398 (3)140.6
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z+1.
 

Footnotes

Current address: Materials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan.

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for providing the grants under the project to strengthen the Materials Chemistry Laboratory.

References

First citationBruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCabrero, A., Alegret, M., Sanchez, R. M., Adzet, T., Laguna, J. C. & Vazquez, M. (2001). Diabetes, 50, 1883–1890.  Web of Science CrossRef PubMed CAS Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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