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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(3R*,4R*)-1-(4-Chloro­phen­yl)-4-[2-hy­dr­oxy-3-(morpholino­methyl)­phen­yl]-3-phen­­oxy­azetidin-2-one

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 21 December 2010; accepted 5 January 2011; online 12 January 2011)

The β-lactam ring of the title compound, C26H25ClN2O4, is nearly planar (r.m.s. deviation = 0.025 Å) and the morpholine ring adopts a chair conformation. The mean plane of the β-lactam ring makes dihedral angles of 21.6 (4), 84.4 (4) and 33.7 (4)° with the two benzene rings and the phenyl ring, respectively. The conformation of the title compound is stabilized by intra­molecular C—H⋯O and O—H⋯N inter­actions. The crystal structure features C—H⋯π and aromatic ππ stacking inter­actions [centroid–centroid distances = 3.684 (4) and 3.883 (4) Å].

Related literature

For a related structure, see: Akkurt et al. (2011[Akkurt, M., Dağdemir, Y., Jarrahpour, A., Rostami, M. & Büyükgüngör, O. (2011). Acta Cryst. E67, o326-o327.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C26H25ClN2O4

  • Mr = 464.93

  • Monoclinic, C 2/c

  • a = 29.6418 (18) Å

  • b = 6.7166 (3) Å

  • c = 28.5708 (15) Å

  • β = 123.043 (4)°

  • V = 4768.2 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 296 K

  • 0.53 × 0.23 × 0.04 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.904, Tmax = 0.992

  • 16824 measured reflections

  • 4707 independent reflections

  • 1712 reflections with I > 2σ(I)

  • Rint = 0.159

Refinement
  • R[F2 > 2σ(F2)] = 0.087

  • wR(F2) = 0.130

  • S = 1.00

  • 4707 reflections

  • 302 parameters

  • 1 restraint

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

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 is a centroid of the C16–C21 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3A⋯N2 0.85 (6) 1.87 (6) 2.642 (8) 150 (5)
C2—H2⋯O2 0.93 2.50 3.304 (6) 144
C15—H15⋯O2 0.93 2.54 3.148 (7) 123
C20—H20⋯Cg5i 0.93 2.88 3.596 (5) 134
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

As part of our ongoing structural studies of β-lactams (Akkurt et al., 2011), we now report the structure of the title compound, (I).

In the title compound, (I), (Fig. 1), the β-lactam ring (N1/C7–C9) is almost planar, with long C—C distances [C7–C9 = 1.518 (7) Å and C7–C8 = 1.553 (6) Å]. The morpholine ring (N2/O4/C23—C26) adopts a chair conformation, with the puckering parameters of QT = 0.594 (8) Å, θ = 177.1 (8)° and ϕ = 305 (17)° (Cremer & Pople, 1975). The dihedral angles between the mean planes of the rings in (I) are given in Table 2.

The molecular conformation of (I) is stabilized by intra-molecular C— H···O and O— H···N interactions (Table 1). The crystal structure is stabilized by C—H⋯π interactions (Table 1) and two π-π stacking interactions [Cg1···Cg5(x, y, z) = 3.684 (4) Å and Cg4···Cg4(1 - x, -y, -z) = 3.883 (4) Å, where Cg1, Cg4 and Cg5 are the centroids of the N1/C7–C9 β-lactam, the C10–C15 and C16–C21 benzene rings, respectively]. Fig. 2 shows the packing of (I), down the b axis.

Related literature top

For a related structure, see: Akkurt et al. (2011). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

To a solution of (E)-2-((4-chlorophenylimino)methyl)-6-(morpholinomethyl)phenol (1.0 mmol) and triethylamine (2.6 mmol) in dry CH2Cl2 was slowly added phenoxyacetyl chloride (1.3 mmol) in dry CH2Cl2 (10 ml) at 195 K. The reaction mixture was then allowed to warm to room temperature, stirred over night and then it was washed with saturated sodium bicarbonate solution (20 ml), brine (20 ml), dried (Na2SO4). The solvent was evaporated under reduced pressure to give the crude product which was then purified by column chromatography over silica gel. Colourless needles were recrystallised from ethyl acetate (yield 65%). [mp: 463–465 K]. IR (KBr, cm-1): 1758.5 (CO β-Lactam), 3311–3497 (OH). 1H-NMR (250 MHz, CDCl3) δ (p.p.m): 3.43 (CH2—N, t, 4H, J = 13.5 Hz), 3.70 (CH2, s, 2H), 3.88 (CH2—O, t, 4H, J = 13.9 Hz), 5.59 (H-8, d, 1H, J = 1.6 Hz), 5.91 (H-7, d, 1H, J = 1.6 Hz), 6.67–7.35 (ArH, m, 12H); 13C-NMR (62.9 MHz, CDCl3) δ (p.p.m): 52.6 (CH2—N), 55.9 (C-22), 50.2 (O—CH2), 66.5 (C-8), 80.9 (C-7), 115.2–157.0 (aromatic carbons), 163.1 (CO β-Lactam). Analysis calculated for C26H25ClN2O4: C 67.17, H 5.42, N 6.03%. found: C 67.05, H 5.47, N 6.08%.

Refinement top

The position of the bridging hydroxyl hydrogen atom was found in a difference Fourier map, and refined freely by the soft- constraint method of the hydrogen-position of 0.83 (2) Å. The other H atoms were placed at calculated positions and were treated as riding on their parent atoms with O—H = 0.82 Å, C—H = 0.93 (aromatic), 0.96(methyl), 0.97 Å (methyline) and 0.98 Å (methine), and with Uiso(H) = 1.5Ueq(C) for methyl and Uiso(H) = 1.2Ueq(C) for aromatic, methine and methyline.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids for non-H atoms drawn at the 20% probability level.
[Figure 2] Fig. 2. The packing of (I), viewing down the b axis. All H atoms are omitted for clarity.
(3R*,4R*)-1-(4-Chlorophenyl)-4-[2-hydroxy-3- (morpholinomethyl)phenyl]-3-phenoxyazetidin-2-one top
Crystal data top
C26H25ClN2O4F(000) = 1952
Mr = 464.93Dx = 1.295 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9239 reflections
a = 29.6418 (18) Åθ = 1.4–26.6°
b = 6.7166 (3) ŵ = 0.20 mm1
c = 28.5708 (15) ÅT = 296 K
β = 123.043 (4)°Needle, colourless
V = 4768.2 (5) Å30.53 × 0.23 × 0.04 mm
Z = 8
Data collection top
Stoe IPDS 2
diffractometer
4707 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1712 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.159
Detector resolution: 6.67 pixels mm-1θmax = 26.2°, θmin = 1.6°
ω scansh = 3636
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 87
Tmin = 0.904, Tmax = 0.992l = 3432
16824 measured reflections
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)] = 0.087Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0198P)2]
where P = (Fo2 + 2Fc2)/3
4707 reflections(Δ/σ)max < 0.001
302 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.15 e Å3
Crystal data top
C26H25ClN2O4V = 4768.2 (5) Å3
Mr = 464.93Z = 8
Monoclinic, C2/cMo Kα radiation
a = 29.6418 (18) ŵ = 0.20 mm1
b = 6.7166 (3) ÅT = 296 K
c = 28.5708 (15) Å0.53 × 0.23 × 0.04 mm
β = 123.043 (4)°
Data collection top
Stoe IPDS 2
diffractometer
4707 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
1712 reflections with I > 2σ(I)
Tmin = 0.904, Tmax = 0.992Rint = 0.159
16824 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0871 restraint
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.15 e Å3
4707 reflectionsΔρmin = 0.15 e Å3
302 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl10.55205 (8)0.0943 (3)0.11446 (7)0.1225 (9)
O10.58355 (13)0.2225 (4)0.21000 (14)0.0705 (15)
O20.53938 (15)0.4640 (5)0.09015 (15)0.0921 (16)
O30.67681 (14)0.3208 (4)0.13843 (16)0.0711 (15)
O40.7152 (2)0.5197 (7)0.0038 (2)0.133 (3)
N10.57506 (14)0.1426 (5)0.09621 (17)0.0565 (16)
N20.74627 (19)0.3438 (6)0.1079 (2)0.080 (2)
C10.58006 (18)0.3860 (7)0.2379 (2)0.064 (2)
C20.57298 (19)0.5775 (7)0.2178 (2)0.073 (2)
C30.5692 (2)0.7320 (7)0.2476 (3)0.085 (3)
C40.5719 (2)0.6941 (8)0.2963 (3)0.097 (3)
C50.5791 (2)0.5024 (9)0.3163 (3)0.103 (3)
C60.5825 (2)0.3474 (7)0.2858 (2)0.082 (3)
C70.60357 (19)0.2554 (6)0.1756 (2)0.059 (2)
C80.61155 (18)0.0579 (6)0.15272 (19)0.0549 (17)
C90.5657 (2)0.3163 (7)0.1150 (2)0.064 (2)
C100.56823 (18)0.0872 (7)0.0456 (2)0.0600 (17)
C110.58087 (19)0.1071 (6)0.0384 (2)0.071 (2)
C120.5758 (2)0.1594 (7)0.0105 (2)0.077 (2)
C130.5587 (2)0.0228 (9)0.0526 (2)0.080 (2)
C140.5446 (2)0.1665 (8)0.0465 (2)0.077 (2)
C150.54974 (18)0.2211 (7)0.0022 (2)0.067 (2)
C160.66644 (18)0.0030 (6)0.16733 (18)0.0544 (16)
C170.69762 (19)0.1335 (6)0.15820 (19)0.0580 (17)
C180.7471 (2)0.0758 (8)0.1678 (2)0.067 (2)
C190.7664 (2)0.1138 (8)0.1899 (2)0.078 (2)
C200.7373 (2)0.2423 (8)0.2011 (2)0.077 (2)
C210.6879 (2)0.1842 (6)0.18915 (19)0.0653 (19)
C220.7803 (2)0.2180 (8)0.1572 (3)0.093 (3)
C230.7780 (3)0.5021 (9)0.1032 (3)0.117 (4)
C240.7411 (4)0.6337 (10)0.0543 (4)0.145 (5)
C250.6841 (2)0.3629 (9)0.0067 (3)0.111 (3)
C260.7192 (2)0.2287 (7)0.0555 (2)0.088 (3)
H20.570700.602800.184500.0890*
H30.564900.862000.234600.1020*
H3A0.6940 (18)0.370 (7)0.125 (2)0.093 (19)*
H40.568800.798300.315800.1160*
H50.581700.476600.349700.1240*
H60.586400.217000.298300.0990*
H70.636400.336300.194500.0700*
H80.594500.053800.159400.0650*
H110.592700.200100.066900.0840*
H120.583900.288600.015300.0920*
H140.531600.257300.075700.0920*
H150.540700.349700.006200.0810*
H190.799700.154000.197200.0940*
H200.751000.366800.216700.0920*
H210.667900.272700.195800.0780*
H22A0.801500.302300.189700.1110*
H22B0.804900.142300.151700.1110*
H23A0.804900.443500.098000.1410*
H23B0.796400.580400.137200.1410*
H24A0.714100.692000.059500.1730*
H24B0.761600.741100.051800.1730*
H25A0.666900.286000.027600.1340*
H25B0.656100.419600.010500.1340*
H26A0.697500.124600.057200.1060*
H26B0.746000.166300.050700.1060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1695 (18)0.1205 (13)0.0933 (13)0.0114 (11)0.0819 (13)0.0060 (10)
O10.100 (3)0.0508 (19)0.086 (3)0.0019 (17)0.067 (2)0.0026 (17)
O20.115 (3)0.070 (2)0.091 (3)0.038 (2)0.056 (2)0.023 (2)
O30.089 (3)0.0445 (18)0.106 (3)0.0007 (17)0.070 (2)0.0045 (17)
O40.208 (5)0.098 (3)0.168 (5)0.024 (3)0.150 (5)0.006 (3)
N10.061 (3)0.050 (2)0.059 (3)0.0081 (19)0.033 (2)0.006 (2)
N20.103 (4)0.060 (3)0.113 (4)0.023 (3)0.083 (3)0.021 (3)
C10.067 (4)0.059 (3)0.084 (4)0.003 (2)0.052 (3)0.001 (3)
C20.088 (4)0.060 (3)0.092 (4)0.001 (3)0.062 (4)0.007 (3)
C30.105 (5)0.058 (3)0.124 (5)0.003 (3)0.083 (4)0.003 (3)
C40.118 (5)0.076 (4)0.140 (6)0.001 (4)0.098 (5)0.017 (4)
C50.145 (6)0.089 (4)0.126 (6)0.001 (4)0.107 (5)0.003 (4)
C60.117 (5)0.062 (3)0.107 (5)0.003 (3)0.086 (4)0.003 (3)
C70.074 (4)0.051 (3)0.067 (4)0.001 (2)0.049 (3)0.003 (2)
C80.060 (3)0.044 (3)0.064 (3)0.005 (2)0.036 (3)0.002 (2)
C90.066 (4)0.058 (3)0.072 (4)0.004 (3)0.041 (3)0.010 (3)
C100.056 (3)0.057 (3)0.062 (3)0.002 (2)0.029 (3)0.005 (3)
C110.083 (4)0.048 (3)0.067 (4)0.001 (3)0.032 (3)0.000 (3)
C120.090 (4)0.063 (3)0.072 (4)0.008 (3)0.040 (4)0.009 (3)
C130.091 (4)0.089 (4)0.060 (4)0.002 (3)0.042 (4)0.004 (3)
C140.084 (4)0.077 (4)0.069 (4)0.011 (3)0.041 (3)0.015 (3)
C150.073 (4)0.064 (3)0.070 (4)0.014 (3)0.042 (3)0.005 (3)
C160.063 (3)0.041 (2)0.060 (3)0.001 (2)0.034 (3)0.001 (2)
C170.063 (3)0.046 (3)0.065 (3)0.007 (2)0.035 (3)0.002 (2)
C180.057 (4)0.073 (3)0.074 (4)0.001 (3)0.037 (3)0.009 (3)
C190.067 (4)0.081 (4)0.069 (4)0.019 (3)0.026 (3)0.009 (3)
C200.079 (4)0.063 (3)0.069 (4)0.017 (3)0.027 (3)0.011 (3)
C210.066 (4)0.053 (3)0.065 (3)0.007 (3)0.028 (3)0.008 (2)
C220.084 (5)0.093 (4)0.118 (5)0.009 (4)0.066 (4)0.010 (4)
C230.165 (7)0.083 (4)0.173 (7)0.048 (5)0.137 (6)0.041 (5)
C240.250 (10)0.069 (4)0.208 (10)0.038 (5)0.185 (9)0.017 (5)
C250.139 (6)0.100 (5)0.124 (6)0.009 (4)0.091 (5)0.015 (4)
C260.108 (5)0.068 (3)0.115 (5)0.014 (3)0.078 (4)0.012 (4)
Geometric parameters (Å, º) top
Cl1—C131.736 (6)C17—C181.392 (9)
O1—C11.394 (6)C18—C221.516 (9)
O1—C71.415 (7)C18—C191.398 (8)
O2—C91.222 (6)C19—C201.376 (9)
O3—C171.379 (5)C20—C211.367 (9)
O4—C241.432 (10)C23—C241.504 (11)
O4—C251.432 (9)C25—C261.502 (8)
O3—H3A0.85 (6)C2—H20.9300
N1—C91.374 (6)C3—H30.9300
N1—C101.397 (7)C4—H40.9300
N1—C81.482 (6)C5—H50.9300
N2—C221.472 (8)C6—H60.9300
N2—C231.473 (10)C7—H70.9800
N2—C261.474 (7)C8—H80.9800
C1—C21.377 (7)C11—H110.9300
C1—C61.356 (7)C12—H120.9300
C2—C31.385 (8)C14—H140.9300
C3—C41.373 (10)C15—H150.9300
C4—C51.377 (8)C19—H190.9300
C5—C61.396 (8)C20—H200.9300
C7—C91.518 (7)C21—H210.9300
C7—C81.553 (6)C22—H22A0.9700
C8—C161.489 (8)C22—H22B0.9700
C10—C151.380 (7)C23—H23A0.9700
C10—C111.404 (7)C23—H23B0.9700
C11—C121.367 (7)C24—H24A0.9700
C12—C131.371 (7)C24—H24B0.9700
C13—C141.379 (8)C25—H25A0.9700
C14—C151.365 (7)C25—H25B0.9700
C16—C171.398 (8)C26—H26A0.9700
C16—C211.394 (6)C26—H26B0.9700
C1—O1—C7117.7 (4)C3—C2—H2120.00
C24—O4—C25110.1 (6)C2—C3—H3120.00
C17—O3—H3A107 (3)C4—C3—H3120.00
C8—N1—C994.8 (4)C3—C4—H4120.00
C9—N1—C10133.2 (4)C5—C4—H4120.00
C8—N1—C10129.3 (4)C4—C5—H5120.00
C22—N2—C23111.3 (5)C6—C5—H5120.00
C23—N2—C26107.9 (5)C1—C6—H6120.00
C22—N2—C26112.4 (4)C5—C6—H6120.00
O1—C1—C6116.6 (4)O1—C7—H7112.00
C2—C1—C6120.8 (5)C8—C7—H7112.00
O1—C1—C2122.6 (5)C9—C7—H7112.00
C1—C2—C3119.2 (5)N1—C8—H8111.00
C2—C3—C4120.3 (5)C7—C8—H8111.00
C3—C4—C5120.3 (6)C16—C8—H8111.00
C4—C5—C6119.1 (6)C10—C11—H11120.00
C1—C6—C5120.4 (5)C12—C11—H11120.00
O1—C7—C8112.1 (4)C11—C12—H12120.00
O1—C7—C9120.3 (5)C13—C12—H12120.00
C8—C7—C986.4 (4)C13—C14—H14120.00
N1—C8—C786.7 (3)C15—C14—H14120.00
N1—C8—C16115.9 (4)C10—C15—H15120.00
C7—C8—C16119.2 (4)C14—C15—H15120.00
O2—C9—C7136.2 (5)C18—C19—H19119.00
N1—C9—C792.0 (4)C20—C19—H19119.00
O2—C9—N1131.6 (5)C19—C20—H20121.00
N1—C10—C11120.0 (4)C21—C20—H20120.00
N1—C10—C15121.3 (4)C16—C21—H21119.00
C11—C10—C15118.8 (5)C20—C21—H21119.00
C10—C11—C12120.0 (4)N2—C22—H22A109.00
C11—C12—C13120.4 (5)N2—C22—H22B109.00
Cl1—C13—C14120.7 (4)C18—C22—H22A109.00
C12—C13—C14119.9 (5)C18—C22—H22B109.00
Cl1—C13—C12119.4 (5)H22A—C22—H22B108.00
C13—C14—C15120.2 (5)N2—C23—H23A110.00
C10—C15—C14120.6 (5)N2—C23—H23B110.00
C8—C16—C17121.7 (4)C24—C23—H23A110.00
C8—C16—C21120.8 (5)C24—C23—H23B110.00
C17—C16—C21117.5 (5)H23A—C23—H23B108.00
O3—C17—C18121.5 (5)O4—C24—H24A110.00
C16—C17—C18121.4 (4)O4—C24—H24B110.00
O3—C17—C16117.1 (5)C23—C24—H24A110.00
C17—C18—C19118.1 (5)C23—C24—H24B110.00
C19—C18—C22120.9 (6)H24A—C24—H24B108.00
C17—C18—C22121.0 (5)O4—C25—H25A109.00
C18—C19—C20121.5 (6)O4—C25—H25B110.00
C19—C20—C21119.0 (5)C26—C25—H25A110.00
C16—C21—C20122.3 (5)C26—C25—H25B109.00
N2—C22—C18111.9 (6)H25A—C25—H25B108.00
N2—C23—C24109.4 (7)N2—C26—H26A110.00
O4—C24—C23109.9 (6)N2—C26—H26B110.00
O4—C25—C26110.7 (6)C25—C26—H26A110.00
N2—C26—C25110.2 (4)C25—C26—H26B109.00
C1—C2—H2120.00H26A—C26—H26B108.00
C7—O1—C1—C227.8 (8)O1—C7—C9—N1115.5 (4)
C7—O1—C1—C6153.9 (5)C9—C7—C8—C16119.7 (5)
C1—O1—C7—C8173.3 (4)C8—C7—C9—N11.9 (4)
C1—O1—C7—C987.5 (5)C9—C7—C8—N11.7 (4)
C24—O4—C25—C2658.8 (8)C7—C8—C16—C21128.8 (5)
C25—O4—C24—C2360.3 (11)N1—C8—C16—C21129.8 (4)
C10—N1—C8—C7161.0 (5)N1—C8—C16—C1748.2 (6)
C9—N1—C8—C16122.9 (4)C7—C8—C16—C1753.2 (6)
C9—N1—C10—C11178.9 (6)N1—C10—C15—C14178.3 (6)
C10—N1—C9—C7159.8 (6)N1—C10—C11—C12177.9 (6)
C8—N1—C10—C15154.4 (5)C15—C10—C11—C121.3 (9)
C10—N1—C8—C1640.0 (7)C11—C10—C15—C141.0 (9)
C8—N1—C9—C72.0 (5)C10—C11—C12—C130.4 (9)
C8—N1—C9—O2177.5 (7)C11—C12—C13—Cl1179.4 (5)
C10—N1—C9—O215.7 (12)C11—C12—C13—C142.4 (10)
C9—N1—C10—C151.9 (10)C12—C13—C14—C152.8 (10)
C8—N1—C10—C1124.8 (9)Cl1—C13—C14—C15179.7 (5)
C9—N1—C8—C71.9 (5)C13—C14—C15—C101.1 (9)
C23—N2—C26—C2558.2 (7)C17—C16—C21—C200.5 (7)
C22—N2—C23—C24176.7 (6)C21—C16—C17—C183.2 (7)
C26—N2—C22—C1868.0 (7)C8—C16—C17—O34.2 (6)
C26—N2—C23—C2459.6 (8)C21—C16—C17—O3177.8 (4)
C22—N2—C26—C25178.7 (6)C8—C16—C21—C20177.5 (4)
C23—N2—C22—C18171.0 (5)C8—C16—C17—C18174.9 (4)
O1—C1—C6—C5179.8 (6)C16—C17—C18—C193.5 (7)
C6—C1—C2—C31.0 (9)O3—C17—C18—C220.4 (7)
O1—C1—C2—C3179.2 (6)O3—C17—C18—C19177.6 (4)
C2—C1—C6—C51.5 (9)C16—C17—C18—C22179.4 (5)
C1—C2—C3—C40.7 (10)C19—C18—C22—N2146.3 (5)
C2—C3—C4—C50.9 (11)C17—C18—C22—N236.7 (7)
C3—C4—C5—C61.3 (11)C22—C18—C19—C20178.3 (5)
C4—C5—C6—C11.6 (10)C17—C18—C19—C201.1 (7)
O1—C7—C9—O269.3 (9)C18—C19—C20—C211.4 (7)
O1—C7—C8—N1123.1 (4)C19—C20—C21—C161.7 (7)
C8—C7—C9—O2177.1 (8)N2—C23—C24—O461.4 (11)
O1—C7—C8—C16118.9 (5)O4—C25—C26—N258.4 (7)
Hydrogen-bond geometry (Å, º) top
Cg5 is a centroid of the C16–C21 benzene ring.
D—H···AD—HH···AD···AD—H···A
O3—H3A···N20.85 (6)1.87 (6)2.642 (8)150 (5)
C2—H2···O20.932.503.304 (6)144
C15—H15···O20.932.543.148 (7)123
C20—H20···Cg5i0.932.883.596 (5)134
Symmetry code: (i) x+3/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC26H25ClN2O4
Mr464.93
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)29.6418 (18), 6.7166 (3), 28.5708 (15)
β (°) 123.043 (4)
V3)4768.2 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.53 × 0.23 × 0.04
Data collection
DiffractometerStoe IPDS 2
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.904, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
16824, 4707, 1712
Rint0.159
(sin θ/λ)max1)0.622
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.087, 0.130, 1.00
No. of reflections4707
No. of parameters302
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.15

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
Cg5 is a centroid of the C16–C21 benzene ring.
D—H···AD—HH···AD···AD—H···A
O3—H3A···N20.85 (6)1.87 (6)2.642 (8)150 (5)
C2—H2···O20.932.503.304 (6)144
C15—H15···O20.932.543.148 (7)123
C20—H20···Cg5i0.932.883.596 (5)134
Symmetry code: (i) x+3/2, y1/2, z+1/2.
The dihedral angles between the mean planes of the rings in (I) (°) top
Ring-2Ring-3Ring-4
Ring-133.7 (4)21.6 (4)84.4 (4)
Ring-213.0 (3)63.0 (3)
Ring-367.6 (3)
Ring-1 : N1/C7–C9 β-lactam ring, Ring-2 : C1–C6 phenyl ring, Ring-3 : C10–C15 benzene ring, Ring-4 : C16–C21 benzene ring.
 

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). AJ, HS, SATB and MA thank the Shiraz University Research Council for financial support (grant No. 89-GR—SC-23).

References

First citationAkkurt, M., Dağdemir, Y., Jarrahpour, A., Rostami, M. & Büyükgüngör, O. (2011). Acta Cryst. E67, o326–o327.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals 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 citationStoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.  Google Scholar

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