1-(4-Meth­oxy­phen­yl)-4-(4-methyl­phen­yl)-3-phen­oxy­azetidin-2-one

Akkurt, M.; Dağdemir, Y.; Jarrahpour, A.; Rostami, M.; Büyükgüngör, O.

doi:10.1107/S1600536811000663

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o326-o327

doi:10.1107/S1600536811000663

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1-(4-Methoxyphenyl)-4-(4-methylphenyl)-3-phenoxyazetidin-2-one

Mehmet Akkurt,^a ^* Yılmaz Dağdemir,^a Aliasghar Jarrahpour,^b Maryam Rostami ^b and Orhan Büyükgüngör ^c

^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 central β-lactam ring of the title compound, C₂₃H₂₁NO₃, is almost planar (r.m.s. deviation = 0.032Å). The methoxybenzene ring is almost coplanar with the β-lactam ring [dihedral angle = 1.87 (11)°], whereas the tolyl ring is almost normal to it [75.73 (12)°]. The dihedral angle between the β-lactam ring and the O-bonded phenyl ring is 51.95 (12)°. An intramolecular C—H⋯O interaction generates an S(6) ring. The crystal structure features intermolecular C—H⋯O hydrogen bonds, forming layers parallel to (011), and weak C—H⋯π interactions. Two aromatic π–π stacking interactions [centroid–centroid distances = 3.6744 (12) and 3.6799 (11) Å] are also observed.

Related literature

For the synthesis of the title compound and background to the biological properties of β-lactam compounds, see: Jarrahpour & Zarei (2010 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₃H₂₁NO₃
M_r = 359.41
Triclinic, $[P \overline 1]$
a = 6.0764 (3) Å
b = 9.9545 (5) Å
c = 16.4519 (10) Å
α = 104.360 (4)°
β = 91.261 (5)°
γ = 97.724 (4)°
V = 953.71 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.60 × 0.37 × 0.12 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.964, T_max = 0.990
13748 measured reflections
3961 independent reflections
2608 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.119
S = 1.03
3961 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C17–C22 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2	0.93	2.47	3.093 (2)	125
C9—H9⋯O2ⁱ	0.98	2.51	3.446 (2)	160
C15—H15⋯O1ⁱ	0.93	2.54	3.435 (2)	162
C19—H19⋯O2ⁱⁱ	0.93	2.54	3.415 (2)	156
C23—H23C⋯O2ⁱⁱⁱ	0.96	2.52	3.184 (2)	126
C5—H5⋯Cg4^iv	0.93	2.96	3.544 (3)	122
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+2, -z+1; (iii) x+1, y+1, z; (iv) x, y-1, z.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000663/hb5783sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000663/hb5783Isup2.hkl

checkCIF report

Comment top

The title compound, (I), is a β-lactam derivative with potential biological properties (Jarrahpour & Zarei, 2010); we now describe its crystal structure. In the title compound (I), (Fig. 1), the β-lactam ring (N1/C7–C9) is nearly planar [r.m.s. deviation = 0.032Å]. The dihedral angles between the planes of the rings in (I) are given in Table 2. The molecular dimensions are normal and lie within expected values for corresponding bond distances and angles (Allen et al., 1987).

The molecular structure is stabilized by intramolecular C—H···O hydrogen bonds, forming an S(6) graph-set motif (Bernstein et al., 1995) (Table 1). In the crystal structure, molecules are linked via intermolecular C—H···O hydrogen bonds (Table 1, Fig. 2), forming layers parallel to the bc plane. In addition, C—H···π interactions and two π-π stacking interactions [Cg1···Cg3(x, y, z) = 3.6744 (12) Å and Cg4···Cg4(1 - x, 2 - y, 1 - z) = 3.6799 (11) Å, where Cg1, Cg3 and Cg4 are the centroids of the N1/C7–C9 β-lactam, the C10–C15 and C17–C22 benzene rings, respectively] contribute to the stabilization of the structure.

Related literature top

For the synthesis of the title compound and background to the biological properties of β-lactam compounds, see: Jarrahpour & Zarei (2010). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared as described by Jarrahpour & Zarei (2010) and colourless prisms of (I) were recrystallized from ethyl acetate.

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

	Fig. 1. The title compound with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. View of the packing of (I) down the a axis. All H atoms are omitted for clarity.

1-(4-Methoxyphenyl)-4-(4-methylphenyl)-3-phenoxyazetidin-2-one top

Crystal data top

C₂₃H₂₁NO₃	Z = 2
M_r = 359.41	F(000) = 380
Triclinic, P1	D_x = 1.252 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0764 (3) Å	Cell parameters from 19074 reflections
b = 9.9545 (5) Å	θ = 2.1–27.6°
c = 16.4519 (10) Å	µ = 0.08 mm⁻¹
α = 104.360 (4)°	T = 296 K
β = 91.261 (5)°	Prism, colourless
γ = 97.724 (4)°	0.60 × 0.37 × 0.12 mm
V = 953.71 (9) Å³

Data collection top

Stoe IPDS 2 diffractometer	3961 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2608 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.055
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.1°
ω scans	h = −7→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
T_min = 0.964, T_max = 0.990	l = −20→20
13748 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0548P)² + 0.0685P] where P = (F_o² + 2F_c²)/3
3961 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₃H₂₁NO₃	γ = 97.724 (4)°
M_r = 359.41	V = 953.71 (9) Å³
Triclinic, P1	Z = 2
a = 6.0764 (3) Å	Mo Kα radiation
b = 9.9545 (5) Å	µ = 0.08 mm⁻¹
c = 16.4519 (10) Å	T = 296 K
α = 104.360 (4)°	0.60 × 0.37 × 0.12 mm
β = 91.261 (5)°

Data collection top

Stoe IPDS 2 diffractometer	3961 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2608 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.990	R_int = 0.055
13748 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	Δρ_max = 0.13 e Å⁻³
3961 reflections	Δρ_min = −0.17 e Å⁻³
246 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

	x	y	z	U_iso*/U_eq
O1	0.1189 (2)	0.46929 (12)	0.24918 (8)	0.0593 (4)
O2	−0.0121 (2)	0.69814 (13)	0.39817 (9)	0.0661 (5)
O3	0.5557 (2)	1.34079 (13)	0.45143 (10)	0.0691 (5)
N1	0.3435 (2)	0.76262 (13)	0.35417 (9)	0.0449 (4)
C1	0.0980 (3)	0.32558 (17)	0.22621 (11)	0.0466 (5)
C2	−0.0981 (3)	0.2579 (2)	0.18159 (14)	0.0659 (7)
C3	−0.1326 (4)	0.1146 (2)	0.15480 (17)	0.0855 (9)
C4	0.0243 (5)	0.0375 (2)	0.17266 (18)	0.0906 (10)
C5	0.2170 (5)	0.1043 (2)	0.21619 (16)	0.0841 (10)
C6	0.2565 (3)	0.2490 (2)	0.24332 (13)	0.0626 (7)
C7	0.2563 (3)	0.54632 (17)	0.32009 (11)	0.0493 (6)
C8	0.1608 (3)	0.67635 (17)	0.36523 (11)	0.0481 (6)
C9	0.4601 (3)	0.65118 (17)	0.30514 (11)	0.0456 (5)
C10	0.5040 (3)	0.66017 (17)	0.21748 (11)	0.0461 (5)
C11	0.3614 (3)	0.7126 (2)	0.17006 (12)	0.0590 (7)
C12	0.4120 (4)	0.7251 (2)	0.09059 (14)	0.0725 (8)
C13	0.6024 (4)	0.6850 (2)	0.05514 (13)	0.0711 (8)
C14	0.7428 (3)	0.6312 (2)	0.10147 (15)	0.0733 (8)
C15	0.6962 (3)	0.6196 (2)	0.18176 (13)	0.0603 (7)
C16	0.6603 (5)	0.7014 (3)	−0.03125 (17)	0.1131 (13)
C17	0.4029 (2)	0.90918 (16)	0.37839 (10)	0.0417 (5)
C18	0.2574 (3)	0.99309 (17)	0.42190 (11)	0.0489 (6)
C19	0.3149 (3)	1.13583 (18)	0.44533 (12)	0.0523 (6)
C20	0.5185 (3)	1.19731 (17)	0.42538 (11)	0.0494 (6)
C21	0.6635 (3)	1.11455 (18)	0.38189 (12)	0.0514 (6)
C22	0.6062 (3)	0.97064 (18)	0.35878 (11)	0.0488 (6)
C23	0.7547 (3)	1.4105 (2)	0.42925 (15)	0.0691 (7)
H2	−0.20600	0.30950	0.16980	0.0790*
H3	−0.26370	0.06920	0.12420	0.1030*
H4	−0.00100	−0.05980	0.15510	0.1090*
H5	0.32400	0.05210	0.22790	0.1010*
H6	0.38930	0.29390	0.27290	0.0750*
H7	0.29430	0.48910	0.35750	0.0590*
H9	0.59590	0.64290	0.33570	0.0550*
H11	0.23000	0.73970	0.19210	0.0710*
H12	0.31430	0.76160	0.06040	0.0870*
H14	0.87190	0.60190	0.07840	0.0880*
H15	0.79530	0.58410	0.21190	0.0720*
H16A	0.77970	0.77730	−0.02580	0.1360*
H16B	0.53250	0.72090	−0.05910	0.1360*
H16C	0.70560	0.61630	−0.06360	0.1360*
H18	0.12050	0.95250	0.43520	0.0590*
H19	0.21710	1.19170	0.47470	0.0630*
H21	0.79960	1.15550	0.36810	0.0620*
H22	0.70480	0.91470	0.32990	0.0590*
H23A	0.75830	1.38950	0.36910	0.0830*
H23B	0.87980	1.37960	0.45200	0.0830*
H23C	0.76110	1.50980	0.45150	0.0830*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0676 (7)	0.0352 (7)	0.0707 (9)	−0.0008 (5)	−0.0211 (6)	0.0116 (6)
O2	0.0539 (7)	0.0533 (8)	0.0853 (10)	−0.0075 (6)	0.0196 (7)	0.0132 (7)
O3	0.0758 (8)	0.0372 (7)	0.0866 (10)	−0.0080 (6)	0.0139 (7)	0.0091 (6)
N1	0.0449 (7)	0.0359 (7)	0.0502 (9)	−0.0019 (6)	0.0055 (6)	0.0079 (6)
C1	0.0499 (9)	0.0379 (9)	0.0504 (10)	0.0010 (7)	0.0033 (7)	0.0112 (8)
C2	0.0555 (10)	0.0520 (12)	0.0820 (15)	0.0035 (9)	−0.0070 (10)	0.0048 (10)
C3	0.0791 (14)	0.0564 (14)	0.102 (2)	−0.0123 (11)	−0.0153 (13)	−0.0020 (12)
C4	0.125 (2)	0.0410 (12)	0.096 (2)	0.0026 (13)	−0.0111 (16)	0.0054 (12)
C5	0.1158 (19)	0.0507 (13)	0.0853 (17)	0.0252 (12)	−0.0183 (14)	0.0114 (12)
C6	0.0673 (11)	0.0499 (11)	0.0688 (13)	0.0097 (9)	−0.0111 (10)	0.0125 (10)
C7	0.0540 (9)	0.0372 (9)	0.0547 (11)	−0.0006 (7)	−0.0069 (8)	0.0125 (8)
C8	0.0474 (9)	0.0409 (9)	0.0536 (11)	−0.0043 (7)	0.0018 (8)	0.0135 (8)
C9	0.0438 (8)	0.0399 (9)	0.0516 (10)	0.0048 (7)	−0.0029 (7)	0.0099 (8)
C10	0.0442 (8)	0.0394 (9)	0.0514 (11)	0.0043 (7)	0.0003 (7)	0.0064 (8)
C11	0.0564 (10)	0.0684 (13)	0.0573 (12)	0.0190 (9)	0.0046 (9)	0.0198 (10)
C12	0.0798 (14)	0.0818 (16)	0.0598 (13)	0.0099 (11)	−0.0018 (11)	0.0267 (11)
C13	0.0748 (13)	0.0746 (15)	0.0527 (13)	−0.0134 (11)	0.0052 (10)	0.0081 (11)
C14	0.0585 (11)	0.0793 (15)	0.0693 (15)	0.0020 (10)	0.0201 (11)	−0.0022 (12)
C15	0.0498 (9)	0.0588 (12)	0.0684 (14)	0.0119 (8)	0.0036 (9)	0.0067 (10)
C16	0.127 (2)	0.132 (3)	0.0654 (17)	−0.0295 (19)	0.0188 (15)	0.0213 (16)
C17	0.0442 (8)	0.0363 (9)	0.0422 (9)	−0.0027 (6)	0.0009 (7)	0.0099 (7)
C18	0.0446 (8)	0.0454 (10)	0.0540 (11)	−0.0025 (7)	0.0118 (7)	0.0116 (8)
C19	0.0547 (9)	0.0424 (10)	0.0568 (11)	0.0033 (8)	0.0126 (8)	0.0080 (8)
C20	0.0562 (9)	0.0366 (9)	0.0517 (11)	−0.0049 (7)	0.0019 (8)	0.0103 (8)
C21	0.0437 (8)	0.0464 (10)	0.0613 (12)	−0.0075 (7)	0.0066 (8)	0.0157 (8)
C22	0.0427 (8)	0.0457 (10)	0.0552 (11)	0.0008 (7)	0.0075 (7)	0.0103 (8)
C23	0.0711 (12)	0.0471 (11)	0.0829 (15)	−0.0178 (9)	−0.0034 (10)	0.0198 (10)

Geometric parameters (Å, º) top

O1—C1	1.373 (2)	C18—C19	1.371 (3)
O1—C7	1.410 (2)	C19—C20	1.388 (3)
O2—C8	1.214 (2)	C20—C21	1.378 (3)
O3—C20	1.371 (2)	C21—C22	1.381 (3)
O3—C23	1.413 (2)	C2—H2	0.9300
N1—C8	1.354 (2)	C3—H3	0.9300
N1—C9	1.475 (2)	C4—H4	0.9300
N1—C17	1.408 (2)	C5—H5	0.9300
C1—C2	1.383 (3)	C6—H6	0.9300
C1—C6	1.371 (3)	C7—H7	0.9800
C2—C3	1.370 (3)	C9—H9	0.9800
C3—C4	1.371 (4)	C11—H11	0.9300
C4—C5	1.358 (4)	C12—H12	0.9300
C5—C6	1.384 (3)	C14—H14	0.9300
C7—C8	1.519 (3)	C15—H15	0.9300
C7—C9	1.574 (3)	C16—H16A	0.9600
C9—C10	1.495 (2)	C16—H16B	0.9600
C10—C11	1.388 (3)	C16—H16C	0.9600
C10—C15	1.383 (3)	C18—H18	0.9300
C11—C12	1.381 (3)	C19—H19	0.9300
C12—C13	1.370 (3)	C21—H21	0.9300
C13—C14	1.376 (3)	C22—H22	0.9300
C13—C16	1.514 (3)	C23—H23A	0.9600
C14—C15	1.386 (3)	C23—H23B	0.9600
C17—C18	1.386 (2)	C23—H23C	0.9600
C17—C22	1.385 (2)

C1—O1—C7	120.21 (14)	C3—C2—H2	120.00
C20—O3—C23	117.71 (15)	C2—C3—H3	120.00
C8—N1—C9	96.00 (13)	C4—C3—H3	120.00
C8—N1—C17	132.78 (13)	C3—C4—H4	120.00
C9—N1—C17	131.20 (13)	C5—C4—H4	120.00
O1—C1—C2	115.45 (16)	C4—C5—H5	120.00
O1—C1—C6	124.67 (17)	C6—C5—H5	120.00
C2—C1—C6	119.87 (17)	C1—C6—H6	120.00
C1—C2—C3	119.70 (19)	C5—C6—H6	120.00
C2—C3—C4	120.6 (2)	O1—C7—H7	113.00
C3—C4—C5	119.5 (2)	C8—C7—H7	113.00
C4—C5—C6	120.9 (2)	C9—C7—H7	113.00
C1—C6—C5	119.4 (2)	N1—C9—H9	112.00
O1—C7—C8	111.20 (14)	C7—C9—H9	112.00
O1—C7—C9	117.37 (14)	C10—C9—H9	111.00
C8—C7—C9	85.70 (13)	C10—C11—H11	120.00
O2—C8—N1	132.64 (17)	C12—C11—H11	120.00
O2—C8—C7	134.97 (17)	C11—C12—H12	119.00
N1—C8—C7	92.39 (14)	C13—C12—H12	119.00
N1—C9—C7	85.80 (12)	C13—C14—H14	119.00
N1—C9—C10	115.03 (14)	C15—C14—H14	119.00
C7—C9—C10	119.15 (15)	C10—C15—H15	120.00
C9—C10—C11	122.47 (16)	C14—C15—H15	120.00
C9—C10—C15	119.98 (17)	C13—C16—H16A	109.00
C11—C10—C15	117.52 (17)	C13—C16—H16B	109.00
C10—C11—C12	120.93 (18)	C13—C16—H16C	109.00
C11—C12—C13	121.6 (2)	H16A—C16—H16B	110.00
C12—C13—C14	117.7 (2)	H16A—C16—H16C	109.00
C12—C13—C16	121.6 (2)	H16B—C16—H16C	109.00
C14—C13—C16	120.7 (2)	C17—C18—H18	120.00
C13—C14—C15	121.53 (19)	C19—C18—H18	120.00
C10—C15—C14	120.74 (18)	C18—C19—H19	120.00
N1—C17—C18	120.09 (13)	C20—C19—H19	120.00
N1—C17—C22	120.40 (14)	C20—C21—H21	120.00
C18—C17—C22	119.52 (16)	C22—C21—H21	120.00
C17—C18—C19	120.12 (16)	C17—C22—H22	120.00
C18—C19—C20	120.29 (17)	C21—C22—H22	120.00
O3—C20—C19	114.80 (16)	O3—C23—H23A	109.00
O3—C20—C21	125.32 (16)	O3—C23—H23B	109.00
C19—C20—C21	119.88 (17)	O3—C23—H23C	109.00
C20—C21—C22	119.83 (17)	H23A—C23—H23B	109.00
C17—C22—C21	120.36 (16)	H23A—C23—H23C	109.00
C1—C2—H2	120.00	H23B—C23—H23C	109.00

C7—O1—C1—C2	154.15 (17)	O1—C7—C8—N1	−120.21 (15)
C7—O1—C1—C6	−26.9 (3)	C9—C7—C8—O2	176.8 (2)
C1—O1—C7—C8	−145.56 (15)	O1—C7—C9—C10	−2.5 (2)
C1—O1—C7—C9	118.10 (17)	C8—C7—C9—N1	2.27 (12)
C23—O3—C20—C21	2.6 (3)	O1—C7—C8—O2	59.0 (3)
C23—O3—C20—C19	−176.70 (17)	N1—C9—C10—C11	−32.4 (2)
C8—N1—C9—C7	−2.55 (13)	N1—C9—C10—C15	145.45 (17)
C17—N1—C8—O2	1.7 (3)	C7—C9—C10—C11	67.2 (2)
C9—N1—C8—O2	−176.6 (2)	C7—C9—C10—C15	−114.9 (2)
C9—N1—C8—C7	2.64 (14)	C9—C10—C15—C14	−178.05 (18)
C17—N1—C8—C7	−179.03 (17)	C15—C10—C11—C12	−0.8 (3)
C17—N1—C9—C7	179.07 (16)	C9—C10—C11—C12	177.14 (18)
C9—N1—C17—C18	177.01 (16)	C11—C10—C15—C14	−0.1 (3)
C8—N1—C17—C22	179.43 (17)	C10—C11—C12—C13	0.8 (3)
C9—N1—C17—C22	−2.8 (3)	C11—C12—C13—C14	0.1 (3)
C8—N1—C17—C18	−0.8 (3)	C11—C12—C13—C16	−178.7 (2)
C8—N1—C9—C10	117.76 (16)	C12—C13—C14—C15	−1.0 (3)
C17—N1—C9—C10	−60.6 (2)	C16—C13—C14—C15	177.9 (2)
O1—C1—C6—C5	−179.42 (19)	C13—C14—C15—C10	1.0 (3)
O1—C1—C2—C3	178.99 (19)	N1—C17—C22—C21	179.40 (16)
C6—C1—C2—C3	0.0 (3)	C18—C17—C22—C21	−0.4 (3)
C2—C1—C6—C5	−0.6 (3)	N1—C17—C18—C19	−179.84 (16)
C1—C2—C3—C4	0.8 (4)	C22—C17—C18—C19	−0.1 (3)
C2—C3—C4—C5	−1.0 (4)	C17—C18—C19—C20	0.3 (3)
C3—C4—C5—C6	0.5 (4)	C18—C19—C20—C21	0.0 (3)
C4—C5—C6—C1	0.3 (4)	C18—C19—C20—O3	179.34 (17)
O1—C7—C9—N1	113.95 (15)	O3—C20—C21—C22	−179.72 (17)
C8—C7—C9—C10	−114.14 (17)	C19—C20—C21—C22	−0.4 (3)
C9—C7—C8—N1	−2.47 (13)	C20—C21—C22—C17	0.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C17–C22 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2	0.93	2.47	3.093 (2)	125
C9—H9···O2ⁱ	0.98	2.51	3.446 (2)	160
C15—H15···O1ⁱ	0.93	2.54	3.435 (2)	162
C19—H19···O2ⁱⁱ	0.93	2.54	3.415 (2)	156
C23—H23C···O2ⁱⁱⁱ	0.96	2.52	3.184 (2)	126
C5—H5···Cg4^iv	0.93	2.96	3.544 (3)	122

Symmetry codes: (i) x+1, y, z; (ii) −x, −y+2, −z+1; (iii) x+1, y+1, z; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₁NO₃
M_r	359.41
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.0764 (3), 9.9545 (5), 16.4519 (10)
α, β, γ (°)	104.360 (4), 91.261 (5), 97.724 (4)
V (Å³)	953.71 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.60 × 0.37 × 0.12

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.964, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	13748, 3961, 2608
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.119, 1.03
No. of reflections	3961
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.17

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

Cg4 is the centroid of the C17–C22 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2	0.93	2.47	3.093 (2)	125
C9—H9···O2ⁱ	0.98	2.51	3.446 (2)	160
C15—H15···O1ⁱ	0.93	2.54	3.435 (2)	162
C19—H19···O2ⁱⁱ	0.93	2.54	3.415 (2)	156
C23—H23C···O2ⁱⁱⁱ	0.96	2.52	3.184 (2)	126
C5—H5···Cg4^iv	0.93	2.96	3.544 (3)	122

Symmetry codes: (i) x+1, y, z; (ii) −x, −y+2, −z+1; (iii) x+1, y+1, z; (iv) x, y−1, z.

The dihedral angles between the mean planes of the rings in (I) (°) top

	Ring-2	Ring-3	Ring-4
Ring-1	51.95 (12)	75.73 (12)	1.87 (11)
Ring-2		86.93 (11)	50.10 (10)
Ring-3			76.54 (9)

Ring-1 : N1/C7–C9 β-lactam ring, Ring-2 : C1–C6 phenyl ring, Ring-3 : C10–C15 benzene ring, Ring-4 : C17–C22 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 and MR thank the Shiraz University Research Council for financial support (grant 88-GR—SC-23).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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Volume 67| Part 2| February 2011| Pages o326-o327

doi:10.1107/S1600536811000663

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