5-Chloro-6-(2-fluoro­benzoyl)-1,3-benzoxazol-2(3H)-one

Aydın, A.; Önkol, T.; Akkurt, M.; Büyükgüngör, O.; Ünlü, S.

doi:10.1107/S1600536804001011

5-Chloro-6-(2-fluorobenzoyl)-1,3-benzoxazol-2(3H)-one

A. Aydın, T. Önkol, M. Akkurt, O. Büyükgüngör and S. Ünlü

The title compound, C₁₇H₁₁ClFNO₅, has a non-planar configuration. The crystal structure is stabilized by the formation of bifurcated N—H

O/O′ hydrogen bonds involving the oxazole N atom and the two carbonyl O atoms of symmetry-related molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001011/su6070sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001011/su6070Isup2.hkl Contains datablock I

CCDC reference: 234896

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.032
wR factor = 0.073
Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   C1       =       7.03 su

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.62 mm
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) .....          0 Ang.
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) .....          0 Ang.
PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) .....          0 Ang.
PLAT151_ALERT_1_C No su (esd) Given on Volume ....................          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    F1     -   C14      =       5.50 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C1       =       6.47 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C14      =       5.16 su

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 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
   4 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (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: PARST (Nardelli, 1995) and WinGX publication routines (Farrugia, 1999).

5-chloro-6-(2-fluorobenzoyl)-1,3-benzoxazol-2(3H)-one top

Crystal data top

C₁₄H₇ClFNO₃	F(000) = 1184
M_r = 291.66	D_x = 1.562 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5958 reflections
a = 7.723 (7) Å	θ = 3.0–56.4°
b = 14.255 (1) Å	µ = 0.33 mm⁻¹
c = 22.530 (2) Å	T = 293 K
V = 2480.4 (4) Å³	Plate, colorless
Z = 8	0.62 × 0.33 × 0.19 mm

Data collection top

Stoe IPDS-2 diffractometer	3080 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1705 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.040
Detector resolution: 6.67 pixels mm^-1	θ_max = 28.3°, θ_min = 1.8°
rotation method scans	h = −8→10
Absorption correction: integration (Stoe & Cie, 2002)	k = −18→18
T_min = 0.823, T_max = 0.941	l = −26→29
10796 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters not refined
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0348P)²] where P = (F_o² + 2F_c²)/3
S = 0.86	(Δ/σ)_max = 0.001
3080 reflections	Δρ_max = 0.14 e Å⁻³
189 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0012 (2)

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 F^{2 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 F^{2. The observed criterion of} ^F2 > σ(F^{2) 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
Cl1	0.05433 (5)	0.41848 (3)	0.43272 (2)	0.0576 (1)
F1	0.3590 (2)	0.42415 (8)	0.27351 (5)	0.0975 (5)
O1	0.72513 (14)	0.59952 (7)	0.41514 (5)	0.0513 (4)
O2	0.78711 (16)	0.74590 (8)	0.44861 (5)	0.0628 (4)
O3	0.30524 (16)	0.25959 (8)	0.41422 (5)	0.0616 (4)
N1	0.51763 (16)	0.67758 (9)	0.46051 (6)	0.0463 (4)
C1	0.6838 (2)	0.68318 (11)	0.44326 (7)	0.0477 (5)
C2	0.4473 (2)	0.59254 (9)	0.44359 (6)	0.0384 (4)
C3	0.2848 (2)	0.55490 (10)	0.44950 (7)	0.0426 (5)
C4	0.2618 (2)	0.46546 (10)	0.42722 (6)	0.0413 (4)
C5	0.39368 (19)	0.41520 (10)	0.39920 (7)	0.0411 (5)
C6	0.5558 (2)	0.45681 (11)	0.39253 (7)	0.0461 (5)
C7	0.57747 (19)	0.54455 (10)	0.41555 (7)	0.0412 (5)
C8	0.3707 (2)	0.31541 (11)	0.38056 (7)	0.0452 (5)
C9	0.4324 (2)	0.28351 (11)	0.32164 (7)	0.0474 (5)
C10	0.4901 (2)	0.19183 (13)	0.31577 (9)	0.0647 (7)
C11	0.5383 (3)	0.15660 (17)	0.26136 (12)	0.0879 (10)
C12	0.5256 (3)	0.2118 (2)	0.21197 (11)	0.0951 (10)
C13	0.4676 (3)	0.3015 (2)	0.21576 (10)	0.0859 (10)
C14	0.4235 (3)	0.33577 (14)	0.27070 (8)	0.0637 (7)
H1	0.46280	0.72080	0.47950	0.060 (5)*
H3	0.19500	0.58780	0.46740	0.048 (4)*
H6	0.64560	0.42600	0.37320	0.050 (4)*
H10	0.49620	0.15340	0.34910	0.072 (6)*
H11	0.57940	0.09550	0.25820	0.128 (10)*
H12	0.55710	0.18750	0.17520	0.132 (10)*
H13	0.45820	0.33890	0.18200	0.125 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0442 (2)	0.0545 (2)	0.0740 (3)	−0.0071 (2)	0.0099 (2)	−0.0097 (2)
F1	0.1437 (12)	0.0669 (7)	0.0818 (8)	0.0003 (8)	0.0034 (8)	0.0227 (6)
O1	0.0437 (6)	0.0445 (6)	0.0657 (7)	−0.0059 (5)	0.0091 (5)	−0.0074 (5)
O2	0.0643 (7)	0.0565 (7)	0.0675 (8)	−0.0230 (7)	0.0022 (6)	−0.0093 (6)
O3	0.0782 (8)	0.0421 (6)	0.0645 (8)	−0.0089 (6)	0.0187 (7)	0.0009 (6)
N1	0.0481 (8)	0.0352 (6)	0.0555 (8)	−0.0005 (6)	0.0044 (6)	−0.0094 (6)
C1	0.0556 (10)	0.0413 (8)	0.0462 (9)	−0.0031 (8)	−0.0008 (8)	−0.0026 (8)
C2	0.0454 (8)	0.0318 (7)	0.0381 (8)	0.0023 (7)	0.0011 (7)	0.0001 (6)
C3	0.0422 (8)	0.0376 (8)	0.0480 (8)	0.0060 (7)	0.0071 (7)	−0.0036 (7)
C4	0.0423 (8)	0.0370 (7)	0.0447 (8)	−0.0012 (7)	0.0043 (7)	0.0012 (7)
C5	0.0456 (8)	0.0361 (8)	0.0415 (8)	0.0009 (7)	0.0055 (7)	−0.0015 (7)
C6	0.0450 (8)	0.0393 (8)	0.0539 (9)	0.0040 (8)	0.0112 (8)	−0.0053 (7)
C7	0.0389 (8)	0.0380 (8)	0.0466 (8)	−0.0025 (6)	0.0046 (7)	0.0004 (7)
C8	0.0456 (9)	0.0388 (8)	0.0511 (9)	−0.0006 (8)	0.0024 (8)	−0.0006 (8)
C9	0.0466 (9)	0.0469 (8)	0.0488 (9)	−0.0035 (7)	0.0039 (8)	−0.0076 (7)
C10	0.0624 (11)	0.0570 (11)	0.0748 (13)	0.0078 (9)	−0.0019 (10)	−0.0196 (11)
C11	0.0728 (14)	0.0879 (16)	0.103 (2)	0.0089 (13)	0.0045 (14)	−0.0492 (15)
C12	0.0743 (15)	0.137 (2)	0.0739 (16)	−0.0221 (16)	0.0175 (13)	−0.0507 (17)
C13	0.0853 (16)	0.119 (2)	0.0535 (13)	−0.0283 (16)	0.0097 (12)	−0.0064 (14)
C14	0.0689 (12)	0.0629 (12)	0.0593 (12)	−0.0109 (10)	0.0084 (10)	−0.0019 (9)

Geometric parameters (Å, º) top

Cl1—C4	1.7410 (16)	C6—C7	1.364 (2)
F1—C14	1.356 (2)	C8—C9	1.482 (2)
O1—C1	1.3876 (19)	C9—C14	1.370 (2)
O1—C7	1.3837 (18)	C9—C10	1.387 (2)
O2—C1	1.204 (2)	C10—C11	1.376 (3)
O3—C8	1.2099 (19)	C11—C12	1.366 (4)
N1—C1	1.343 (2)	C12—C13	1.358 (4)
N1—C2	1.3820 (18)	C13—C14	1.374 (3)
N1—H1	0.8614	C3—H3	0.9293
C2—C7	1.370 (2)	C6—H6	0.9293
C2—C3	1.371 (2)	C10—H10	0.9307
C3—C4	1.382 (2)	C11—H11	0.9297
C4—C5	1.396 (2)	C12—H12	0.9303
C5—C8	1.494 (2)	C13—H13	0.9317
C5—C6	1.394 (2)

Cl1···O3	3.0098 (13)	C5···F1	2.8473 (19)
Cl1···H3ⁱ	2.9631	C6···C14	3.399 (2)
Cl1···H13ⁱⁱ	2.9186	C6···F1	3.117 (2)
Cl1···H1ⁱⁱⁱ	3.0115	C7···C3^vi	3.519 (2)
F1···C5	2.8473 (19)	C8···O2^x	3.212 (2)
F1···C6	3.117 (2)	C9···C12ⁱⁱ	3.390 (3)
F1···H11^iv	2.5890	C10···O1^x	3.403 (2)
O1···C10^v	3.403 (2)	C12···C14^xi	3.566 (3)
O2···O3^vi	3.1726 (16)	C12···C9^xi	3.390 (3)
O2···N1^vii	2.9243 (17)	C13···C14^xi	3.568 (3)
O2···C8^v	3.212 (2)	C14···C12ⁱⁱ	3.566 (3)
O3···C1^vi	3.3141 (19)	C14···C6	3.399 (2)
O3···O2^vi	3.1726 (16)	C14···C13ⁱⁱ	3.568 (3)
O3···Cl1	3.0098 (13)	C1···H1^vii	3.0894
O3···C3ⁱⁱⁱ	3.1031 (18)	C2···H12^iv	2.9994
O3···N1ⁱⁱⁱ	2.9448 (17)	C7···H12^iv	3.0680
O3···N1^vi	3.2618 (18)	C9···H6	2.8612
O3···C2ⁱⁱⁱ	3.1484 (18)	H1···O2^viii	2.1656
O1···H10^v	2.7268	H1···C1^viii	3.0894
O2···H1^vii	2.1656	H1···Cl1^ix	3.0115
O3···H10	2.5727	H1···O3^ix	2.5989
O3···H1ⁱⁱⁱ	2.5989	H3···Cl1ⁱ	2.9631
O3···H3ⁱⁱⁱ	2.7263	H3···O3^ix	2.7263
N1···O2^viii	2.9243 (17)	H6···C9	2.8612
N1···O3^vi	3.2618 (18)	H10···O3	2.5727
N1···O3^ix	2.9448 (17)	H10···O1^x	2.7268
C1···O3^vi	3.3141 (19)	H11···F1^xii	2.5890
C2···O3^ix	3.1484 (18)	H12···C2^xii	2.9994
C3···O3^ix	3.1031 (18)	H12···C7^xii	3.0680
C3···C7^vi	3.519 (2)	H13···Cl1^xi	2.9186

C1—O1—C7	107.10 (11)	O3—C8—C5	119.98 (14)
C1—N1—C2	110.35 (13)	C10—C9—C14	116.65 (16)
C2—N1—H1	124.83	C8—C9—C10	118.54 (15)
C1—N1—H1	124.81	C8—C9—C14	124.57 (15)
O2—C1—N1	130.40 (15)	C9—C10—C11	121.04 (19)
O1—C1—O2	122.10 (14)	C10—C11—C12	119.7 (2)
O1—C1—N1	107.51 (13)	C11—C12—C13	121.0 (2)
N1—C2—C7	106.07 (13)	C12—C13—C14	118.3 (2)
N1—C2—C3	132.54 (13)	C9—C14—C13	123.3 (2)
C3—C2—C7	121.39 (13)	F1—C14—C9	118.98 (16)
C2—C3—C4	116.32 (14)	F1—C14—C13	117.61 (18)
Cl1—C4—C3	116.58 (12)	C2—C3—H3	121.85
C3—C4—C5	122.96 (14)	C4—C3—H3	121.83
Cl1—C4—C5	120.41 (11)	C5—C6—H6	121.33
C4—C5—C8	121.95 (13)	C7—C6—H6	121.33
C4—C5—C6	119.06 (14)	C9—C10—H10	119.60
C6—C5—C8	118.80 (13)	C11—C10—H10	119.36
C5—C6—C7	117.35 (14)	C10—C11—H11	120.16
O1—C7—C2	108.97 (12)	C12—C11—H11	120.11
C2—C7—C6	122.88 (14)	C11—C12—H12	119.47
O1—C7—C6	128.15 (14)	C13—C12—H12	119.54
O3—C8—C9	119.61 (14)	C12—C13—H13	120.89
C5—C8—C9	120.39 (13)	C14—C13—H13	120.85

C7—O1—C1—O2	−178.64 (15)	C4—C5—C8—O3	−45.5 (2)
C7—O1—C1—N1	0.78 (16)	C4—C5—C8—C9	136.33 (16)
C1—O1—C7—C2	−0.36 (16)	C8—C5—C6—C7	−173.36 (14)
C1—O1—C7—C6	179.42 (16)	C6—C5—C8—O3	129.44 (17)
C2—N1—C1—O1	−0.92 (17)	C5—C6—C7—O1	179.28 (15)
C2—N1—C1—O2	178.43 (16)	C5—C6—C7—C2	−1.0 (2)
C1—N1—C2—C3	−178.30 (16)	C5—C8—C9—C14	−37.5 (2)
C1—N1—C2—C7	0.70 (17)	O3—C8—C9—C10	−30.0 (2)
C7—C2—C3—C4	1.8 (2)	O3—C8—C9—C14	144.31 (19)
N1—C2—C7—O1	−0.19 (16)	C5—C8—C9—C10	148.22 (15)
N1—C2—C7—C6	−179.98 (15)	C14—C9—C10—C11	1.1 (3)
N1—C2—C3—C4	−179.34 (15)	C8—C9—C14—F1	2.1 (3)
C3—C2—C7—C6	−0.9 (2)	C8—C9—C14—C13	−174.08 (19)
C3—C2—C7—O1	178.94 (13)	C8—C9—C10—C11	175.77 (17)
C2—C3—C4—Cl1	−178.28 (11)	C10—C9—C14—F1	176.44 (17)
C2—C3—C4—C5	−1.0 (2)	C10—C9—C14—C13	0.3 (3)
Cl1—C4—C5—C8	−8.7 (2)	C9—C10—C11—C12	−1.5 (3)
C3—C4—C5—C6	−0.8 (2)	C10—C11—C12—C13	0.7 (4)
C3—C4—C5—C8	174.15 (14)	C11—C12—C13—C14	0.6 (4)
Cl1—C4—C5—C6	176.42 (12)	C12—C13—C14—F1	−177.3 (2)
C4—C5—C6—C7	1.7 (2)	C12—C13—C14—C9	−1.1 (4)
C6—C5—C8—C9	−48.7 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^viii	0.86	2.17	2.9243 (17)	147
N1—H1···O3^ix	0.86	2.60	2.9448 (17)	105

Symmetry codes: (viii) x−1/2, −y+3/2, −z+1; (ix) −x+1/2, y+1/2, z.

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5-Chloro-6-(2-fluoro­benzoyl)-1,3-benzoxazol-2(3H)-one

Supporting information

Key indicators

checkCIF/PLATON results

5-Chloro-6-(2-fluorobenzoyl)-1,3-benzoxazol-2(3H)-one