3-Phen­oxy-1,4-diphenyl­azetidin-2-one

In the structure of the title compound, C₂₁H₁₇NO₂, the four-membered β-lactam ring is nearly planar, with long C—C distances of 1.526 (3) and 1.567 (3) Å. The angles between the planes of the three phenyl rings and this group are 81.12 (8), 3.02 (8) and 49.88 (7)°. The dihedral angles between the planes of the phenyl rings are 83.72 (7), 68.03 (7) and 47.06 (6)°. The crystal structure is stabilized by inter- and intra­molecular C—H...O hydrogen-bond inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.114
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

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

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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-Phenoxy-1,4-diphenylazetidin-2-one

Crystal data

C21H17NO2	Z = 2
Mr = 315.36	F(000) = 332
Triclinic, P1	Dx = 1.277 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0985 (9) Å	Cell parameters from 14524 reflections
b = 9.5020 (16) Å	θ = 2.3–28.1°
c = 15.318 (2) Å	µ = 0.08 mm^−1
α = 74.815 (12)°	T = 296 K
β = 87.578 (12)°	Prismatic stick, colorless
γ = 73.355 (12)°	0.80 × 0.38 × 0.09 mm
V = 820.2 (2) Å^3

Data collection

Stoe IPDS-II diffractometer	2112 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	Rint = 0.084
Plane graphite monochromator	θmax = 27.6°, θmin = 2.3°
Detector resolution: 6.67 pixels mm^-1	h = −7→7
ω scans	k = −12→12
9578 measured reflections	l = −19→19
3689 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0496P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
3689 reflections	Δρmax = 0.12 e Å^−3
218 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.9047 (2)	0.52491 (15)	0.24770 (8)	0.0465 (4)
O2	1.0081 (2)	0.78466 (19)	0.09585 (9)	0.0644 (5)
N1	0.6245 (2)	0.85378 (19)	0.14142 (9)	0.0426 (5)
C1	0.7601 (3)	0.6176 (2)	0.17285 (12)	0.0436 (6)
C2	0.8338 (3)	0.7599 (2)	0.12889 (11)	0.0466 (6)
C3	0.5284 (3)	0.7294 (2)	0.19051 (11)	0.0411 (6)
C4	0.4746 (3)	0.7240 (2)	0.28809 (11)	0.0397 (6)
C5	0.6034 (3)	0.7692 (3)	0.34206 (12)	0.0511 (7)
C6	0.5551 (4)	0.7576 (3)	0.43245 (14)	0.0623 (8)
C7	0.3781 (4)	0.7009 (3)	0.46946 (14)	0.0651 (8)
C8	0.2484 (4)	0.6564 (3)	0.41665 (15)	0.0623 (8)
C9	0.2956 (3)	0.6682 (2)	0.32607 (13)	0.0514 (7)
C10	0.5249 (3)	1.0123 (2)	0.11658 (11)	0.0422 (6)
C11	0.6493 (3)	1.1109 (3)	0.07112 (12)	0.0523 (7)
C12	0.5473 (4)	1.2649 (3)	0.04899 (13)	0.0602 (8)
C13	0.3237 (4)	1.3251 (3)	0.07087 (14)	0.0620 (8)
C14	0.1991 (4)	1.2271 (3)	0.11423 (14)	0.0590 (8)
C15	0.2973 (3)	1.0723 (3)	0.13709 (12)	0.0508 (7)
C16	0.8869 (3)	0.3799 (2)	0.28445 (11)	0.0413 (6)
C17	0.7077 (3)	0.3285 (2)	0.26630 (13)	0.0484 (6)
C18	0.7155 (4)	0.1773 (3)	0.30368 (15)	0.0610 (8)
C19	0.8977 (4)	0.0787 (3)	0.35934 (16)	0.0676 (9)
C20	1.0723 (4)	0.1335 (3)	0.37863 (15)	0.0624 (8)
C21	1.0684 (3)	0.2827 (2)	0.34209 (12)	0.0506 (7)
H1	0.74250	0.56180	0.12940	0.0520*
H3	0.39940	0.72420	0.15670	0.0490*
H5	0.72310	0.80760	0.31750	0.0610*
H6	0.64240	0.78810	0.46820	0.0750*
H7	0.34640	0.69280	0.53020	0.0780*
H8	0.12870	0.61830	0.44160	0.0750*
H9	0.20670	0.63840	0.29050	0.0620*
H11	0.79990	1.07230	0.05600	0.0630*
H12	0.63010	1.33020	0.01860	0.0720*
H13	0.25780	1.42990	0.05670	0.0740*
H14	0.04760	1.26650	0.12800	0.0710*
H15	0.21240	1.00750	0.16620	0.0610*
H17	0.58340	0.39450	0.22950	0.0580*
H18	0.59620	0.14200	0.29110	0.0730*
H19	0.90320	−0.02290	0.38350	0.0810*
H20	1.19430	0.06830	0.41700	0.0750*
H21	1.18630	0.31820	0.35590	0.0610*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0442 (7)	0.0456 (8)	0.0472 (7)	−0.0137 (6)	−0.0092 (5)	−0.0052 (6)
O2	0.0393 (7)	0.0822 (12)	0.0603 (8)	−0.0184 (7)	0.0092 (6)	0.0009 (8)
N1	0.0364 (8)	0.0486 (10)	0.0392 (8)	−0.0154 (7)	0.0046 (6)	−0.0025 (7)
C1	0.0426 (10)	0.0485 (12)	0.0378 (9)	−0.0120 (8)	−0.0030 (7)	−0.0084 (8)
C2	0.0388 (10)	0.0604 (13)	0.0351 (9)	−0.0137 (9)	−0.0002 (7)	−0.0036 (8)
C3	0.0354 (9)	0.0475 (12)	0.0392 (9)	−0.0152 (8)	−0.0023 (7)	−0.0051 (8)
C4	0.0353 (9)	0.0409 (11)	0.0396 (9)	−0.0100 (8)	0.0020 (7)	−0.0059 (7)
C5	0.0555 (11)	0.0579 (13)	0.0455 (10)	−0.0262 (10)	0.0029 (8)	−0.0123 (9)
C6	0.0746 (14)	0.0691 (16)	0.0450 (11)	−0.0195 (12)	−0.0009 (10)	−0.0186 (11)
C7	0.0724 (14)	0.0634 (15)	0.0426 (11)	−0.0007 (12)	0.0114 (10)	−0.0072 (10)
C8	0.0522 (12)	0.0652 (16)	0.0578 (13)	−0.0145 (11)	0.0183 (10)	−0.0012 (11)
C9	0.0432 (10)	0.0549 (13)	0.0531 (11)	−0.0183 (9)	0.0046 (8)	−0.0047 (9)
C10	0.0444 (10)	0.0507 (12)	0.0295 (8)	−0.0160 (9)	−0.0001 (7)	−0.0044 (8)
C11	0.0534 (11)	0.0606 (15)	0.0411 (10)	−0.0236 (10)	0.0037 (8)	−0.0025 (9)
C12	0.0777 (15)	0.0560 (15)	0.0478 (11)	−0.0313 (12)	0.0001 (10)	−0.0012 (10)
C13	0.0805 (15)	0.0489 (14)	0.0505 (12)	−0.0125 (12)	−0.0038 (10)	−0.0082 (10)
C14	0.0598 (12)	0.0591 (15)	0.0522 (12)	−0.0075 (11)	0.0051 (9)	−0.0155 (10)
C15	0.0477 (11)	0.0545 (14)	0.0458 (10)	−0.0142 (10)	0.0070 (8)	−0.0069 (9)
C16	0.0428 (9)	0.0442 (11)	0.0373 (9)	−0.0109 (8)	0.0048 (7)	−0.0134 (8)
C17	0.0454 (10)	0.0532 (13)	0.0484 (10)	−0.0139 (9)	0.0000 (8)	−0.0163 (9)
C18	0.0643 (13)	0.0614 (16)	0.0680 (13)	−0.0272 (12)	0.0077 (11)	−0.0256 (12)
C19	0.0839 (16)	0.0467 (14)	0.0701 (15)	−0.0195 (12)	0.0054 (12)	−0.0110 (11)
C20	0.0626 (13)	0.0508 (14)	0.0609 (13)	−0.0036 (11)	−0.0081 (10)	−0.0050 (10)
C21	0.0458 (10)	0.0517 (13)	0.0494 (11)	−0.0085 (9)	−0.0050 (8)	−0.0097 (9)

Geometric parameters (Å, º)

O1—C1	1.407 (2)	C16—C21	1.388 (3)
O1—C16	1.379 (2)	C17—C18	1.388 (3)
O2—C2	1.215 (2)	C18—C19	1.380 (4)
N1—C2	1.371 (2)	C19—C20	1.385 (4)
N1—C3	1.483 (2)	C20—C21	1.375 (3)
N1—C10	1.406 (3)	C1—H1	0.9800
C1—C2	1.526 (3)	C3—H3	0.9800
C1—C3	1.567 (3)	C5—H5	0.9300
C3—C4	1.508 (2)	C6—H6	0.9300
C4—C5	1.385 (3)	C7—H7	0.9300
C4—C9	1.388 (3)	C8—H8	0.9300
C5—C6	1.386 (3)	C9—H9	0.9300
C6—C7	1.378 (4)	C11—H11	0.9300
C7—C8	1.373 (4)	C12—H12	0.9300
C8—C9	1.387 (3)	C13—H13	0.9300
C10—C11	1.400 (3)	C14—H14	0.9300
C10—C15	1.398 (3)	C15—H15	0.9300
C11—C12	1.371 (4)	C17—H17	0.9300
C12—C13	1.384 (4)	C18—H18	0.9300
C13—C14	1.387 (4)	C19—H19	0.9300
C14—C15	1.374 (4)	C20—H20	0.9300
C16—C17	1.383 (3)	C21—H21	0.9300
O1···O2	3.108 (2)	C3···H17	3.0000
O1···N1	3.138 (2)	C3···H15	2.7300
O1···C5	3.153 (3)	C4···H15	2.9100
O2···C11	3.180 (3)	C6···H20^vi	3.0900
O2···O1	3.108 (2)	C8···H19^vi	3.1000
O2···C3^i	3.389 (2)	C13···H1^iii	2.9800
O2···C11^ii	3.361 (2)	C16···H14^vii	2.9000
O1···H9^i	2.5700	C17···H1	2.6700
O2···H3^i	2.4500	C17···H14^vii	2.9500
O2···H11	2.5800	C17···H7^v	3.0800
O2···H11^ii	2.7700	C18···H7^v	3.0700
O2···H12^ii	2.9000	H1···C17	2.6700
N1···O1	3.138 (2)	H1···H17	2.3000
N1···H5	2.6800	H1···C13^iii	2.9800
C2···C5	3.512 (3)	H3···O2^iv	2.4500
C2···C13^iii	3.595 (3)	H3···H9	2.3900
C3···C17	3.530 (3)	H5···N1	2.6800
C3···O2^iv	3.389 (2)	H5···C2	3.0600
C4···C16	3.520 (3)	H7···C17^v	3.0800
C4···C15	3.409 (3)	H7···C18^v	3.0700
C5···C10	3.581 (3)	H9···O1^iv	2.5700
C5···C2	3.512 (3)	H9···H3	2.3900
C5···O1	3.153 (3)	H11···O2	2.5800
C7···C7^v	3.558 (4)	H11···C2	2.8300
C7···C8^v	3.544 (4)	H11···O2^ii	2.7700
C8···C7^v	3.544 (4)	H12···O2^ii	2.9000
C10···C5	3.581 (3)	H12···H13^viii	2.5400
C11···O2	3.180 (3)	H13···H12^viii	2.5400
C11···O2^ii	3.361 (2)	H14···C16^vi	2.9000
C13···C2^iii	3.595 (3)	H14···C17^vi	2.9500
C14···C16^vi	3.537 (3)	H15···C3	2.7300
C15···C4	3.409 (3)	H15···C4	2.9100
C16···C14^vii	3.537 (3)	H17···C1	2.5800
C16···C4	3.520 (3)	H17···C3	3.0000
C17···C3	3.530 (3)	H17···H1	2.3000
C1···H17	2.5800	H19···C8^vii	3.1000
C2···H5	3.0600	H20···C6^vii	3.0900
C2···H11	2.8300
C1—O1—C16	118.13 (14)	O1—C1—H1	113.00
C2—N1—C3	95.40 (15)	C2—C1—H1	113.00
C2—N1—C10	134.15 (15)	C3—C1—H1	113.00
C3—N1—C10	130.44 (15)	N1—C3—H3	112.00
O1—C1—C2	111.31 (15)	C1—C3—H3	112.00
O1—C1—C3	118.39 (14)	C4—C3—H3	112.00
C2—C1—C3	86.11 (14)	C4—C5—H5	120.00
O2—C2—N1	132.67 (18)	C6—C5—H5	120.00
O2—C2—C1	135.29 (18)	C5—C6—H6	120.00
N1—C2—C1	92.04 (14)	C7—C6—H6	120.00
N1—C3—C1	86.30 (13)	C6—C7—H7	120.00
N1—C3—C4	115.89 (15)	C8—C7—H7	120.00
C1—C3—C4	116.48 (15)	C7—C8—H8	120.00
C3—C4—C5	121.76 (17)	C9—C8—H8	120.00
C3—C4—C9	119.43 (16)	C4—C9—H9	120.00
C5—C4—C9	118.78 (16)	C8—C9—H9	120.00
C4—C5—C6	120.4 (2)	C10—C11—H11	120.00
C5—C6—C7	120.2 (2)	C12—C11—H11	120.00
C6—C7—C8	120.0 (2)	C11—C12—H12	119.00
C7—C8—C9	120.1 (2)	C13—C12—H12	119.00
C4—C9—C8	120.55 (19)	C12—C13—H13	120.00
N1—C10—C11	121.12 (18)	C14—C13—H13	120.00
N1—C10—C15	119.42 (18)	C13—C14—H14	120.00
C11—C10—C15	119.5 (2)	C15—C14—H14	120.00
C10—C11—C12	119.5 (2)	C10—C15—H15	120.00
C11—C12—C13	121.3 (2)	C14—C15—H15	120.00
C12—C13—C14	119.1 (3)	C16—C17—H17	120.00
C13—C14—C15	120.7 (2)	C18—C17—H17	120.00
C10—C15—C14	119.9 (2)	C17—C18—H18	120.00
O1—C16—C17	124.68 (16)	C19—C18—H18	120.00
O1—C16—C21	114.99 (16)	C18—C19—H19	121.00
C17—C16—C21	120.32 (17)	C20—C19—H19	121.00
C16—C17—C18	119.25 (19)	C19—C20—H20	119.00
C17—C18—C19	120.9 (2)	C21—C20—H20	119.00
C18—C19—C20	118.9 (2)	C16—C21—H21	120.00
C19—C20—C21	121.1 (2)	C20—C21—H21	120.00
C16—C21—C20	119.43 (19)
C16—O1—C1—C2	−168.38 (15)	N1—C3—C4—C5	−32.6 (3)
C16—O1—C1—C3	94.27 (19)	C1—C3—C4—C9	−111.4 (2)
C1—O1—C16—C21	164.67 (16)	C9—C4—C5—C6	0.5 (3)
C1—O1—C16—C17	−14.2 (3)	C3—C4—C9—C8	177.4 (2)
C3—N1—C10—C15	−1.6 (3)	C5—C4—C9—C8	−0.7 (3)
C3—N1—C2—O2	−176.3 (2)	C3—C4—C5—C6	−177.6 (2)
C2—N1—C3—C1	−3.03 (13)	C4—C5—C6—C7	0.0 (4)
C10—N1—C3—C1	175.94 (17)	C5—C6—C7—C8	−0.3 (4)
C2—N1—C3—C4	114.70 (17)	C6—C7—C8—C9	0.1 (4)
C10—N1—C3—C4	−66.3 (2)	C7—C8—C9—C4	0.4 (4)
C2—N1—C10—C15	177.00 (18)	N1—C10—C11—C12	−179.20 (17)
C10—N1—C2—C1	−175.80 (18)	N1—C10—C15—C14	179.13 (17)
C3—N1—C2—C1	3.11 (13)	C15—C10—C11—C12	1.3 (3)
C2—N1—C10—C11	−2.5 (3)	C11—C10—C15—C14	−1.3 (3)
C3—N1—C10—C11	178.88 (16)	C10—C11—C12—C13	0.2 (3)
C10—N1—C2—O2	4.8 (3)	C11—C12—C13—C14	−1.5 (3)
C3—C1—C2—N1	−2.94 (13)	C12—C13—C14—C15	1.4 (3)
C2—C1—C3—N1	2.72 (12)	C13—C14—C15—C10	0.0 (3)
O1—C1—C3—C4	−2.3 (2)	O1—C16—C17—C18	176.47 (18)
C3—C1—C2—O2	176.5 (2)	C17—C16—C21—C20	2.2 (3)
C2—C1—C3—C4	−114.46 (17)	O1—C16—C21—C20	−176.79 (18)
O1—C1—C2—N1	−121.95 (15)	C21—C16—C17—C18	−2.4 (3)
O1—C1—C3—N1	114.88 (16)	C16—C17—C18—C19	0.8 (3)
O1—C1—C2—O2	57.5 (3)	C17—C18—C19—C20	1.0 (4)
C1—C3—C4—C5	66.7 (3)	C18—C19—C20—C21	−1.2 (4)
N1—C3—C4—C9	149.28 (17)	C19—C20—C21—C16	−0.4 (3)

Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+2, −z; (iii) −x+1, −y+2, −z; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1; (vi) x−1, y+1, z; (vii) x+1, y−1, z; (viii) −x+1, −y+3, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2^iv	0.98	2.45	3.389 (2)	160
C9—H9···O1^iv	0.93	2.57	3.455 (2)	160
C11—H11···O2	0.93	2.58	3.180 (3)	123

Symmetry code: (iv) x−1, y, z.