3-Phenyl­isoxazolin-5-one: a redetermination

The structure of the title mol­ecule, C₉H₇NO₂, has been redetermined to improved precision and the H atoms located [Cannas et al. (1969). Acta Cryst. B25, 1050]. The five-membered ring is almost planar (r.m.s. deviation = 0.006 Å) and subtends a dihedral angle of 2.45 (6)° with the benzene ring. In the crystal, mol­ecules form ribbons running parallel to the a-axis direction through a combination of C—H...N and C—H...O hydrogen bonds. `Stair-step' offset π–π stacking inter­actions are also observed.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.089
• Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         14 Report

Alert level G
PLAT395_ALERT_2_G Deviating  X-O-Y   Angle from 120 Deg for  O1          109.6 Degre
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         11 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-Phenylisoxazolin-5-one

Crystal data

C9H7NO2	F(000) = 336
Mr = 161.16	Dx = 1.448 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 9.9869 (6) Å	Cell parameters from 4379 reflections
b = 5.3008 (3) Å	θ = 5.6–72.1°
c = 13.9874 (9) Å	µ = 0.86 mm^−1
β = 93.106 (2)°	T = 150 K
V = 739.39 (8) Å^3	Plate, orange
Z = 4	0.19 × 0.12 × 0.06 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	1433 independent reflections
Radiation source: INCOATEC IµS micro-focus source	1282 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.4167 pixels mm^-1	θmax = 72.1°, θmin = 5.3°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −6→5
Tmin = 0.83, Tmax = 0.95	l = −17→17
5465 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	All H-atom parameters refined
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0441P)^2 + 0.1913P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
1433 reflections	Δρmax = 0.26 e Å^−3
138 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0097 (11)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.72988 (8)	0.35740 (17)	0.61102 (6)	0.0291 (3)
O2	0.83139 (9)	0.67872 (19)	0.68908 (7)	0.0345 (3)
N1	0.59421 (10)	0.2725 (2)	0.59036 (8)	0.0276 (3)
C1	0.51416 (12)	0.4307 (2)	0.62725 (8)	0.0219 (3)
C2	0.58547 (12)	0.6434 (2)	0.67731 (9)	0.0254 (3)
H2A	0.5637 (15)	0.811 (3)	0.6485 (11)	0.033 (4)*
H2B	0.5708 (16)	0.650 (3)	0.7461 (12)	0.036 (4)*
C3	0.72877 (12)	0.5762 (2)	0.66339 (9)	0.0260 (3)
C4	0.36809 (12)	0.3949 (2)	0.61691 (8)	0.0223 (3)
C5	0.31305 (13)	0.1913 (2)	0.56468 (9)	0.0270 (3)
H5	0.3730 (16)	0.070 (3)	0.5343 (11)	0.037 (4)*
C6	0.17523 (13)	0.1648 (3)	0.55302 (9)	0.0308 (3)
H6	0.1396 (18)	0.020 (4)	0.5152 (13)	0.050 (5)*
C7	0.09063 (13)	0.3393 (3)	0.59296 (9)	0.0297 (3)
H7	−0.0084 (17)	0.321 (3)	0.5830 (11)	0.035 (4)*
C8	0.14499 (13)	0.5399 (3)	0.64548 (9)	0.0293 (3)
H8	0.0864 (18)	0.661 (3)	0.6743 (12)	0.043 (4)*
C9	0.28324 (12)	0.5680 (2)	0.65752 (9)	0.0258 (3)
H9	0.3184 (16)	0.708 (3)	0.6934 (11)	0.037 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0220 (4)	0.0294 (5)	0.0360 (5)	0.0020 (3)	0.0029 (4)	−0.0048 (4)
O2	0.0227 (5)	0.0418 (6)	0.0390 (5)	−0.0033 (4)	0.0001 (4)	−0.0054 (4)
N1	0.0234 (5)	0.0263 (6)	0.0329 (6)	0.0000 (4)	0.0018 (4)	−0.0038 (4)
C1	0.0237 (6)	0.0192 (6)	0.0228 (5)	0.0013 (4)	0.0010 (4)	0.0023 (5)
C2	0.0218 (6)	0.0232 (6)	0.0311 (6)	0.0008 (5)	0.0001 (5)	−0.0028 (5)
C3	0.0240 (6)	0.0280 (6)	0.0259 (6)	0.0007 (5)	0.0014 (5)	0.0009 (5)
C4	0.0242 (6)	0.0204 (6)	0.0221 (6)	−0.0006 (4)	0.0001 (4)	0.0028 (5)
C5	0.0294 (6)	0.0230 (6)	0.0285 (6)	−0.0005 (5)	0.0004 (5)	−0.0008 (5)
C6	0.0315 (7)	0.0289 (7)	0.0313 (7)	−0.0070 (5)	−0.0036 (5)	−0.0008 (5)
C7	0.0247 (6)	0.0337 (7)	0.0305 (6)	−0.0036 (5)	−0.0014 (5)	0.0060 (5)
C8	0.0248 (6)	0.0306 (7)	0.0328 (7)	0.0023 (5)	0.0033 (5)	0.0018 (6)
C9	0.0252 (6)	0.0238 (6)	0.0284 (6)	0.0003 (5)	0.0011 (5)	−0.0012 (5)

Geometric parameters (Å, º)

O1—C3	1.3720 (16)	C4—C5	1.3990 (17)
O1—N1	1.4420 (13)	C5—C6	1.3843 (18)
O2—C3	1.1980 (16)	C5—H5	0.991 (17)
N1—C1	1.2857 (16)	C6—C7	1.390 (2)
C1—C4	1.4704 (16)	C6—H6	0.988 (19)
C1—C2	1.4881 (17)	C7—C8	1.386 (2)
C2—C3	1.4977 (16)	C7—H7	0.995 (16)
C2—H2A	0.995 (16)	C8—C9	1.3899 (17)
C2—H2B	0.981 (16)	C8—H8	0.972 (18)
C4—C9	1.3913 (17)	C9—H9	0.952 (17)
C3—O1—N1	109.63 (8)	C5—C4—C1	120.71 (11)
C1—N1—O1	108.30 (10)	C6—C5—C4	119.98 (12)
N1—C1—C4	120.76 (11)	C6—C5—H5	120.2 (9)
N1—C1—C2	113.00 (10)	C4—C5—H5	119.8 (9)
C4—C1—C2	126.23 (10)	C5—C6—C7	120.49 (12)
C1—C2—C3	101.24 (10)	C5—C6—H6	118.0 (11)
C1—C2—H2A	113.4 (9)	C7—C6—H6	121.5 (11)
C3—C2—H2A	110.5 (9)	C8—C7—C6	119.61 (12)
C1—C2—H2B	113.2 (9)	C8—C7—H7	120.3 (9)
C3—C2—H2B	109.3 (9)	C6—C7—H7	120.1 (9)
H2A—C2—H2B	109.0 (13)	C7—C8—C9	120.30 (12)
O2—C3—O1	120.81 (11)	C7—C8—H8	120.1 (10)
O2—C3—C2	131.38 (12)	C9—C8—H8	119.6 (10)
O1—C3—C2	107.81 (10)	C8—C9—C4	120.18 (12)
C9—C4—C5	119.43 (11)	C8—C9—H9	118.9 (9)
C9—C4—C1	119.84 (11)	C4—C9—H9	120.9 (10)
C3—O1—N1—C1	0.43 (13)	N1—C1—C4—C5	−1.60 (17)
O1—N1—C1—C4	179.36 (9)	C2—C1—C4—C5	177.44 (11)
O1—N1—C1—C2	0.20 (14)	C9—C4—C5—C6	0.62 (18)
N1—C1—C2—C3	−0.68 (14)	C1—C4—C5—C6	−177.90 (11)
C4—C1—C2—C3	−179.79 (11)	C4—C5—C6—C7	−0.07 (19)
N1—O1—C3—O2	179.42 (11)	C5—C6—C7—C8	−0.5 (2)
N1—O1—C3—C2	−0.86 (13)	C6—C7—C8—C9	0.56 (19)
C1—C2—C3—O2	−179.41 (14)	C7—C8—C9—C4	−0.01 (19)
C1—C2—C3—O1	0.91 (12)	C5—C4—C9—C8	−0.58 (18)
N1—C1—C4—C9	179.89 (11)	C1—C4—C9—C8	177.95 (11)
C2—C1—C4—C9	−1.07 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N1^i	0.995 (16)	2.602 (16)	3.5525 (17)	160.0 (12)
C5—H5···N1^ii	0.991 (17)	2.55 (2)	3.438 (2)	149 (1)
C8—H8···O2^iii	0.972 (18)	2.57 (2)	3.306 (2)	133 (1)

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