(3S*,4S*)-1,3,4-Triphenyl­azetidin-2-one

In the crystal structure of the title compound, C₂₁H₁₇NO, the nitro­gen configuration is almost planar.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.036
• wR factor = 0.077
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

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Computing details

Data collection: PROCESS-AUTO (Rigaku,1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).

(I)

Crystal data

C21H17NO	F(000) = 632.00
Mr = 299.37	Dx = 1.241 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 11258 reflections
a = 9.016 (3) Å	θ = 3.1–27.5°
b = 8.752 (3) Å	µ = 0.08 mm^−1
c = 20.664 (8) Å	T = 296 K
β = 100.614 (14)°	Platelet, colorless
V = 1602.7 (10) Å^3	0.36 × 0.30 × 0.12 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	Rint = 0.030
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°
ω scans	h = −11→11
15391 measured reflections	k = −11→11
3669 independent reflections	l = −26→26
2161 reflections with F^2 > 2.0σ(F^2)

Refinement

Refinement on F^2	w = 1/[0.0001Fo^2 + 1.1σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.036	(Δ/σ)max < 0.001
wR(F^2) = 0.077	Δρmax = 0.22 e Å^−3
S = 1.00	Δρmin = −0.18 e Å^−3
3669 reflections	Extinction correction: Larson (1970)
209 parameters	Extinction coefficient: 519 (31)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.01120 (9)	0.42040 (10)	0.15838 (4)	0.0774 (2)
N1	0.17655 (9)	0.63038 (10)	0.17528 (4)	0.0541 (2)
C1	0.07887 (10)	0.59075 (12)	0.25859 (6)	0.0554 (3)
C2	0.19156 (10)	0.71175 (12)	0.23879 (5)	0.0509 (3)
C3	0.07615 (11)	0.52482 (13)	0.19024 (6)	0.0580 (3)
C4	0.12439 (10)	0.48815 (12)	0.31659 (5)	0.0530 (3)
C5	0.22813 (12)	0.37125 (13)	0.31522 (6)	0.0674 (3)
C6	0.26662 (13)	0.27453 (17)	0.36843 (8)	0.0831 (4)
C7	0.20294 (17)	0.29205 (19)	0.42309 (8)	0.0897 (5)
C8	0.10095 (18)	0.4060 (2)	0.42481 (6)	0.0907 (5)
C9	0.06224 (12)	0.50405 (16)	0.37219 (6)	0.0713 (4)
C10	0.34738 (10)	0.72451 (12)	0.27950 (5)	0.0473 (2)
C11	0.46847 (11)	0.64163 (12)	0.26606 (6)	0.0572 (3)
C12	0.60986 (12)	0.65953 (13)	0.30504 (6)	0.0672 (3)
C13	0.63073 (12)	0.75786 (16)	0.35743 (6)	0.0738 (4)
C14	0.51054 (12)	0.84009 (16)	0.37152 (6)	0.0728 (4)
C15	0.36935 (12)	0.82405 (12)	0.33245 (5)	0.0586 (3)
C16	0.21990 (11)	0.67543 (12)	0.11622 (5)	0.0533 (3)
C17	0.16952 (12)	0.59697 (14)	0.05786 (6)	0.0643 (3)
C18	0.21041 (13)	0.64842 (17)	0.00057 (6)	0.0765 (4)
C19	0.30166 (13)	0.77446 (18)	0.00051 (6)	0.0802 (4)
C20	0.35196 (13)	0.85077 (16)	0.05836 (6)	0.0767 (4)
C21	0.31217 (12)	0.80129 (13)	0.11619 (6)	0.0653 (3)
H1	−0.0188	0.6377	0.2606	0.066*
H2	0.1447	0.8129	0.2323	0.060*
H5	0.2747	0.3598	0.2762	0.082*
H6	0.3388	0.1917	0.3665	0.099*
H7	0.2311	0.2240	0.4610	0.106*
H8	0.0542	0.4176	0.4637	0.111*
H9	−0.0105	0.5864	0.3741	0.087*
H11	0.4538	0.5707	0.2287	0.068*
H12	0.6957	0.6010	0.2952	0.080*
H13	0.7312	0.7699	0.3846	0.086*
H14	0.5254	0.9096	0.4093	0.086*
H15	0.2838	0.8837	0.3418	0.070*
H17	0.1049	0.5069	0.0578	0.075*
H18	0.1754	0.5934	−0.0407	0.091*
H19	0.3280	0.8107	−0.0408	0.097*
H20	0.4185	0.9394	0.0589	0.092*
H21	0.3475	0.8557	0.1576	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0775 (5)	0.0834 (6)	0.0658 (5)	−0.0284 (4)	−0.0008 (4)	−0.0115 (4)
N1	0.0562 (4)	0.0579 (5)	0.0460 (5)	−0.0057 (4)	0.0034 (4)	−0.0048 (4)
C1	0.0412 (5)	0.0660 (7)	0.0583 (7)	0.0003 (4)	0.0072 (4)	−0.0048 (5)
C2	0.0525 (5)	0.0500 (6)	0.0488 (6)	0.0043 (4)	0.0057 (4)	−0.0047 (5)
C3	0.0476 (5)	0.0662 (8)	0.0562 (7)	−0.0048 (5)	−0.0012 (4)	−0.0030 (6)
C4	0.0440 (5)	0.0613 (7)	0.0534 (6)	−0.0102 (5)	0.0081 (4)	−0.0083 (5)
C5	0.0649 (6)	0.0698 (8)	0.0697 (8)	0.0017 (6)	0.0181 (5)	0.0016 (7)
C6	0.0812 (8)	0.0700 (9)	0.0951 (11)	0.0004 (7)	0.0081 (8)	0.0119 (8)
C7	0.1071 (10)	0.0870 (11)	0.0701 (10)	−0.0222 (9)	0.0030 (8)	0.0155 (8)
C8	0.1110 (11)	0.1043 (12)	0.0611 (9)	−0.0192 (9)	0.0275 (8)	−0.0034 (9)
C9	0.0693 (7)	0.0828 (9)	0.0647 (8)	−0.0050 (6)	0.0200 (6)	−0.0106 (7)
C10	0.0501 (5)	0.0486 (6)	0.0432 (5)	−0.0043 (4)	0.0082 (4)	0.0025 (5)
C11	0.0552 (5)	0.0563 (7)	0.0595 (7)	0.0001 (5)	0.0091 (5)	−0.0008 (5)
C12	0.0523 (6)	0.0697 (8)	0.0787 (9)	0.0013 (5)	0.0098 (5)	0.0142 (7)
C13	0.0581 (7)	0.0881 (10)	0.0690 (8)	−0.0182 (6)	−0.0043 (6)	0.0153 (7)
C14	0.0767 (7)	0.0851 (9)	0.0531 (7)	−0.0237 (7)	0.0024 (6)	−0.0080 (6)
C15	0.0604 (6)	0.0638 (7)	0.0524 (7)	−0.0073 (5)	0.0128 (5)	−0.0060 (5)
C16	0.0517 (5)	0.0587 (7)	0.0470 (6)	0.0044 (5)	0.0024 (4)	−0.0004 (5)
C17	0.0655 (6)	0.0704 (8)	0.0526 (7)	0.0012 (5)	−0.0005 (5)	−0.0062 (6)
C18	0.0873 (8)	0.0909 (10)	0.0483 (7)	0.0055 (7)	0.0043 (6)	−0.0088 (7)
C19	0.0895 (8)	0.0979 (11)	0.0550 (8)	0.0067 (8)	0.0177 (6)	0.0083 (8)
C20	0.0850 (8)	0.0798 (9)	0.0663 (8)	−0.0082 (7)	0.0161 (7)	0.0069 (7)
C21	0.0745 (7)	0.0684 (8)	0.0514 (7)	−0.0079 (6)	0.0078 (5)	−0.0018 (6)

Geometric parameters (Å, º)

O1—C3	1.2122 (14)	C17—C18	1.3787 (18)
N1—C2	1.4773 (13)	C18—C19	1.376 (2)
N1—C3	1.3681 (14)	C19—C20	1.3715 (19)
N1—C16	1.4048 (14)	C20—C21	1.3792 (19)
C1—C2	1.5730 (15)	C1—H1	0.980
C1—C3	1.5217 (17)	C2—H2	0.980
C1—C4	1.4933 (15)	C5—H5	0.980
C2—C10	1.5029 (12)	C6—H6	0.980
C4—C5	1.3900 (15)	C7—H7	0.980
C4—C9	1.3750 (16)	C8—H8	0.980
C5—C6	1.380 (2)	C9—H9	0.980
C6—C7	1.367 (2)	C11—H11	0.980
C7—C8	1.361 (2)	C12—H12	0.980
C8—C9	1.379 (2)	C13—H13	0.980
C10—C11	1.3809 (14)	C14—H14	0.980
C10—C15	1.3840 (14)	C15—H15	0.980
C11—C12	1.3857 (14)	C17—H17	0.980
C12—C13	1.3686 (17)	C18—H18	0.980
C13—C14	1.3760 (18)	C19—H19	0.980
C14—C15	1.3833 (14)	C20—H20	0.980
C16—C17	1.3894 (15)	C21—H21	0.980
C16—C21	1.3805 (16)
C2—N1—C3	94.64 (8)	C2—C1—H1	111.0
C2—N1—C16	129.93 (8)	C3—C1—H1	109.8
C3—N1—C16	133.43 (8)	C4—C1—H1	109.5
C2—C1—C3	85.10 (8)	N1—C2—H2	110.3
C2—C1—C4	121.22 (7)	C1—C2—H2	111.2
C3—C1—C4	118.16 (9)	C10—C2—H2	110.2
N1—C2—C1	87.06 (7)	C4—C5—H5	118.9
N1—C2—C10	117.15 (8)	C6—C5—H5	120.6
C1—C2—C10	119.11 (8)	C5—C6—H6	119.5
O1—C3—N1	131.30 (11)	C7—C6—H6	120.0
O1—C3—C1	135.52 (11)	C6—C7—H7	120.4
N1—C3—C1	93.18 (8)	C8—C7—H7	120.1
C1—C4—C5	120.85 (10)	C7—C8—H8	119.5
C1—C4—C9	121.04 (10)	C9—C8—H8	119.9
C5—C4—C9	118.09 (10)	C4—C9—H9	119.1
C4—C5—C6	120.43 (12)	C8—C9—H9	120.0
C5—C6—C7	120.48 (13)	C10—C11—H11	119.6
C6—C7—C8	119.50 (14)	C12—C11—H11	120.4
C7—C8—C9	120.63 (14)	C11—C12—H12	119.8
C4—C9—C8	120.86 (12)	C13—C12—H12	119.6
C2—C10—C11	122.72 (9)	C12—C13—H13	120.0
C2—C10—C15	118.18 (9)	C14—C13—H13	120.2
C11—C10—C15	119.10 (8)	C13—C14—H14	119.7
C10—C11—C12	120.03 (10)	C15—C14—H14	120.3
C11—C12—C13	120.57 (11)	C10—C15—H15	119.3
C12—C13—C14	119.83 (10)	C14—C15—H15	120.2
C13—C14—C15	119.96 (11)	C16—C17—H17	119.9
C10—C15—C14	120.50 (10)	C18—C17—H17	120.9
N1—C16—C17	121.10 (9)	C17—C18—H18	119.5
N1—C16—C21	119.24 (9)	C19—C18—H18	119.3
C17—C16—C21	119.65 (10)	C18—C19—H19	120.1
C16—C17—C18	119.17 (11)	C20—C19—H19	120.5
C17—C18—C19	121.13 (12)	C19—C20—H20	119.9
C18—C19—C20	119.43 (13)	C21—C20—H20	119.7
C19—C20—C21	120.35 (12)	C16—C21—H21	119.1
C16—C21—C20	120.26 (11)	C20—C21—H21	120.6