Methyl [6-(2-chloro­benzo­yl)-2-oxo-2,3-dihydro-1,3-benzoxazol-3-yl]acetate

Aydın, A.; Dündar, Y.; Akkurt, M.; Büyükgüngör, O.; Şahin, M.F.

doi:10.1107/S160053680700178X

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Methyl [6-(2-chlorobenzoyl)-2-oxo-2,3-dihydro-1,3-benzoxazol-3-yl]acetate

A. Aydın, Y. Dündar, M. Akkurt, O. Büyükgüngör and M. F. Şahin

In the molecular structure of the title compound, C₁₇H₁₂ClNO₅, the 1,3-benzoxazole ring system makes a dihedral angle of 72.96 (7)° with the benzene ring of the 2-chlorobenzoyl group. In the crystal structure, two intramolecular C—H

O hydrogen bonds influence the molecular conformation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700178X/wn2108sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680700178X/wn2108Isup2.hkl Contains datablock I

CCDC reference: 636831

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R factor = 0.034
wR factor = 0.092
Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.62 mm
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         500 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

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, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Methyl [6-(2-chlorobenzoyl)-2-oxo-2,3-dihydro-1,3-benzoxazol-3-yl]acetate top

Crystal data top

C₁₇H₁₂ClNO₅	Z = 2
M_r = 345.73	F(000) = 356
Triclinic, P1	D_x = 1.464 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0189 (5) Å	Cell parameters from 23409 reflections
b = 10.0329 (7) Å	θ = 3.0–27.8°
c = 12.2791 (8) Å	µ = 0.27 mm⁻¹
α = 112.968 (5)°	T = 296 K
β = 95.782 (5)°	Prism, colourless
γ = 95.013 (5)°	0.62 × 0.54 × 0.39 mm
V = 784.48 (10) Å³

Data collection top

Stoe IPDS-2 diffractometer	3044 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2631 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.054
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 3.0°
ω scans	h = −8→8
Absorption correction: integration (XRED32; Stoe & Cie, 2002)	k = −12→12
T_min = 0.850, T_max = 0.902	l = −15→15
16110 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0475P)² + 0.1526P] where P = (F_o² + 2F_c²)/3
3044 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Special details top

Experimental. IR v_max (cm^-1) (KBr): 1779, 1762, 1664 (Ünlü et al., 2003).

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
Cl1	0.29410 (8)	0.02639 (5)	0.59208 (5)	0.0768 (2)
O1	0.15222 (17)	0.40830 (14)	0.80361 (10)	0.0583 (4)
O2	−0.26301 (13)	0.30596 (11)	0.39807 (9)	0.0443 (3)
O3	−0.38951 (16)	0.29026 (15)	0.21597 (11)	0.0614 (4)
O4	0.13961 (18)	0.07747 (12)	0.12604 (10)	0.0568 (4)
O5	0.20125 (16)	0.20884 (13)	0.01887 (10)	0.0543 (4)
N1	−0.06079 (17)	0.29482 (13)	0.26793 (11)	0.0433 (4)
C1	0.4320 (2)	0.30199 (15)	0.75176 (12)	0.0399 (4)
C2	0.5691 (2)	0.40206 (17)	0.84361 (14)	0.0499 (5)
C3	0.7390 (2)	0.3605 (2)	0.87772 (16)	0.0629 (6)
C4	0.7740 (3)	0.2186 (2)	0.82246 (18)	0.0660 (7)
C5	0.6398 (3)	0.1166 (2)	0.73267 (17)	0.0621 (6)
C6	0.4702 (2)	0.15924 (16)	0.69764 (13)	0.0479 (5)
C7	0.24471 (19)	0.35095 (14)	0.72306 (12)	0.0402 (4)
C8	0.17726 (19)	0.33257 (14)	0.59945 (12)	0.0391 (4)
C9	0.30687 (19)	0.32571 (16)	0.51894 (13)	0.0425 (4)
C10	0.24694 (19)	0.31415 (16)	0.40410 (13)	0.0436 (4)
C11	0.05094 (19)	0.30729 (14)	0.37244 (12)	0.0382 (4)
C12	−0.07716 (18)	0.31377 (14)	0.45244 (12)	0.0374 (4)
C13	−0.02144 (19)	0.32778 (15)	0.56605 (12)	0.0399 (4)
C14	−0.2510 (2)	0.29607 (16)	0.28422 (13)	0.0444 (4)
C15	0.0089 (2)	0.30237 (18)	0.16350 (14)	0.0505 (5)
C16	0.1226 (2)	0.18060 (16)	0.10251 (12)	0.0417 (4)
C17	0.3192 (3)	0.1057 (2)	−0.04947 (19)	0.0731 (7)
H2	0.54580	0.49800	0.88230	0.0600*
H3	0.83050	0.42870	0.93840	0.0760*
H4	0.88920	0.19140	0.84590	0.0790*
H5	0.66280	0.02020	0.69600	0.0750*
H9	0.43770	0.32900	0.54310	0.0510*
H10	0.33420	0.31120	0.35130	0.0520*
H13	−0.10990	0.33380	0.61880	0.0480*
H15A	0.09010	0.39520	0.18690	0.0610*
H15B	−0.10050	0.29890	0.10710	0.0610*
H17A	0.34450	0.03950	−0.01240	0.1100*
H17B	0.43920	0.15720	−0.05230	0.1100*
H17C	0.25250	0.05180	−0.12930	0.1100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0962 (4)	0.0412 (2)	0.0721 (3)	0.0025 (2)	−0.0118 (3)	0.0079 (2)
O1	0.0558 (6)	0.0763 (8)	0.0447 (6)	0.0236 (6)	0.0176 (5)	0.0210 (5)
O2	0.0316 (5)	0.0555 (6)	0.0479 (6)	0.0089 (4)	0.0070 (4)	0.0222 (5)
O3	0.0446 (6)	0.0832 (8)	0.0577 (7)	0.0137 (5)	−0.0010 (5)	0.0308 (6)
O4	0.0726 (8)	0.0523 (6)	0.0528 (6)	0.0191 (5)	0.0152 (5)	0.0252 (5)
O5	0.0571 (6)	0.0648 (7)	0.0490 (6)	0.0145 (5)	0.0184 (5)	0.0277 (5)
N1	0.0411 (6)	0.0523 (7)	0.0394 (6)	0.0129 (5)	0.0078 (5)	0.0198 (5)
C1	0.0421 (7)	0.0433 (7)	0.0355 (7)	0.0064 (5)	0.0065 (5)	0.0168 (6)
C2	0.0503 (8)	0.0509 (8)	0.0439 (8)	0.0002 (6)	0.0015 (6)	0.0168 (6)
C3	0.0479 (9)	0.0863 (13)	0.0548 (9)	−0.0063 (8)	−0.0057 (7)	0.0350 (9)
C4	0.0497 (9)	0.1000 (15)	0.0695 (11)	0.0247 (9)	0.0112 (8)	0.0530 (11)
C5	0.0718 (11)	0.0676 (10)	0.0616 (10)	0.0334 (9)	0.0203 (9)	0.0342 (9)
C6	0.0558 (9)	0.0452 (8)	0.0436 (8)	0.0109 (6)	0.0072 (6)	0.0180 (6)
C7	0.0406 (7)	0.0392 (7)	0.0400 (7)	0.0065 (5)	0.0092 (6)	0.0141 (6)
C8	0.0379 (7)	0.0383 (6)	0.0407 (7)	0.0077 (5)	0.0077 (5)	0.0145 (5)
C9	0.0322 (6)	0.0511 (8)	0.0453 (7)	0.0089 (5)	0.0079 (5)	0.0193 (6)
C10	0.0360 (7)	0.0547 (8)	0.0435 (7)	0.0102 (6)	0.0131 (6)	0.0209 (6)
C11	0.0391 (7)	0.0379 (6)	0.0384 (7)	0.0093 (5)	0.0086 (5)	0.0148 (5)
C12	0.0307 (6)	0.0382 (6)	0.0441 (7)	0.0075 (5)	0.0081 (5)	0.0164 (5)
C13	0.0365 (7)	0.0429 (7)	0.0425 (7)	0.0081 (5)	0.0123 (5)	0.0173 (6)
C14	0.0393 (7)	0.0469 (7)	0.0467 (8)	0.0092 (6)	0.0052 (6)	0.0181 (6)
C15	0.0585 (9)	0.0575 (9)	0.0460 (8)	0.0203 (7)	0.0152 (7)	0.0278 (7)
C16	0.0401 (7)	0.0489 (7)	0.0364 (7)	0.0068 (6)	0.0024 (5)	0.0180 (6)
C17	0.0656 (11)	0.0915 (14)	0.0649 (11)	0.0242 (10)	0.0314 (9)	0.0263 (10)

Geometric parameters (Å, º) top

Cl1—C6	1.7394 (16)	C8—C9	1.396 (2)
O1—C7	1.2171 (18)	C8—C13	1.4047 (19)
O2—C12	1.3854 (16)	C9—C10	1.387 (2)
O2—C14	1.3741 (18)	C10—C11	1.3796 (19)
O3—C14	1.1995 (19)	C11—C12	1.3842 (19)
O4—C16	1.190 (2)	C12—C13	1.3588 (19)
O5—C16	1.3243 (19)	C15—C16	1.506 (2)
O5—C17	1.440 (2)	C2—H2	0.9300
N1—C11	1.3901 (18)	C3—H3	0.9300
N1—C14	1.3702 (19)	C4—H4	0.9300
N1—C15	1.444 (2)	C5—H5	0.9300
C1—C2	1.391 (2)	C9—H9	0.9300
C1—C6	1.387 (2)	C10—H10	0.9300
C1—C7	1.499 (2)	C13—H13	0.9300
C2—C3	1.376 (2)	C15—H15A	0.9700
C3—C4	1.374 (3)	C15—H15B	0.9700
C4—C5	1.375 (3)	C17—H17A	0.9600
C5—C6	1.384 (3)	C17—H17B	0.9600
C7—C8	1.4776 (19)	C17—H17C	0.9600

Cl1···C8	3.2180 (16)	C11···C13ⁱⁱⁱ	3.468 (2)
Cl1···C9	3.4506 (18)	C11···C12ⁱⁱⁱ	3.540 (2)
Cl1···O2ⁱ	3.3725 (13)	C11···O4	3.1692 (18)
Cl1···C12ⁱ	3.4253 (16)	C12···C12ⁱⁱⁱ	3.483 (2)
Cl1···C13ⁱ	3.5689 (16)	C12···Cl1ⁱ	3.4253 (16)
O1···C3ⁱⁱ	3.178 (2)	C12···C11ⁱⁱⁱ	3.540 (2)
O1···C4ⁱⁱ	3.211 (3)	C13···C11ⁱⁱⁱ	3.468 (2)
O1···C15ⁱⁱⁱ	3.102 (2)	C13···Cl1ⁱ	3.5689 (16)
O2···Cl1ⁱ	3.3725 (13)	C14···C8ⁱⁱⁱ	3.399 (2)
O2···N1	2.2195 (16)	C14···C7ⁱⁱⁱ	3.574 (2)
O3···C17ⁱⁱ	3.394 (2)	C15···O1ⁱⁱⁱ	3.102 (2)
O3···C7ⁱⁱⁱ	3.414 (2)	C16···O4^iv	3.2284 (19)
O4···C16^iv	3.2284 (19)	C16···C10	3.398 (2)
O4···C10	3.2719 (19)	C17···C6^ix	3.594 (3)
O4···C11	3.1692 (18)	C17···O4^iv	3.412 (3)
O4···O4^iv	3.2138 (17)	C17···O3^vii	3.394 (2)
O4···C4^v	3.361 (3)	C1···H9	2.6800
O4···C17^iv	3.412 (2)	C3···H15A^x	3.0400
O4···N1	2.7989 (18)	C4···H17B^viii	3.0800
O1···H13	2.5900	C5···H17B^viii	3.0200
O1···H15Aⁱⁱⁱ	2.6900	C6···H9	3.0100
O1···H2	2.7800	C15···H10	3.0500
O1···H3ⁱⁱ	2.9100	C16···H10	2.9800
O1···H15Bⁱⁱⁱ	2.7800	C17···H17A^xi	3.0600
O2···H10ⁱⁱ	2.8400	H2···O1	2.7800
O2···H9ⁱⁱ	2.8600	H3···O1^vii	2.9100
O3···H15B	2.5500	H4···O5^xii	2.8400
O3···H10ⁱⁱ	2.6500	H4···O4^v	2.8400
O4···H17A	2.2800	H9···O2^vii	2.8600
O4···H4^v	2.8400	H9···C1	2.6800
O5···H4^vi	2.8400	H9···C6	3.0100
N1···O2	2.2195 (16)	H10···O2^vii	2.8400
N1···O4	2.7989 (18)	H10···O3^vii	2.6500
C3···O1^vii	3.178 (2)	H10···C15	3.0500
C4···O1^vii	3.211 (3)	H10···C16	2.9800
C4···O4^v	3.361 (3)	H13···O1	2.5900
C6···C9	3.407 (2)	H15A···O1ⁱⁱⁱ	2.6900
C6···C17^viii	3.594 (3)	H15A···C3^x	3.0400
C7···C14ⁱⁱⁱ	3.574 (2)	H15B···O3	2.5500
C7···O3ⁱⁱⁱ	3.414 (2)	H15B···O1ⁱⁱⁱ	2.7800
C8···C14ⁱⁱⁱ	3.399 (2)	H17A···O4	2.2800
C8···Cl1	3.2180 (16)	H17A···C17^xi	3.0600
C9···Cl1	3.4506 (18)	H17A···H17A^xi	2.4200
C9···C6	3.407 (2)	H17B···C4^ix	3.0800
C10···C16	3.398 (2)	H17B···C5^ix	3.0200
C10···O4	3.2719 (19)

C12—O2—C14	107.54 (10)	O2—C14—N1	107.95 (12)
C16—O5—C17	117.00 (15)	O3—C14—N1	129.23 (14)
C11—N1—C14	109.45 (12)	N1—C15—C16	113.18 (15)
C11—N1—C15	126.73 (12)	O4—C16—O5	126.05 (14)
C14—N1—C15	123.16 (12)	O4—C16—C15	125.83 (14)
C2—C1—C6	118.06 (14)	O5—C16—C15	108.12 (14)
C2—C1—C7	118.33 (14)	C1—C2—H2	120.00
C6—C1—C7	123.42 (13)	C3—C2—H2	120.00
C1—C2—C3	120.62 (16)	C2—C3—H3	120.00
C2—C3—C4	120.26 (17)	C4—C3—H3	120.00
C3—C4—C5	120.45 (19)	C3—C4—H4	120.00
C4—C5—C6	119.11 (19)	C5—C4—H4	120.00
Cl1—C6—C1	119.76 (11)	C4—C5—H5	120.00
Cl1—C6—C5	118.54 (14)	C6—C5—H5	120.00
C1—C6—C5	121.48 (15)	C8—C9—H9	119.00
O1—C7—C1	118.79 (13)	C10—C9—H9	119.00
O1—C7—C8	121.02 (13)	C9—C10—H10	122.00
C1—C7—C8	120.17 (12)	C11—C10—H10	122.00
C7—C8—C9	121.39 (12)	C8—C13—H13	122.00
C7—C8—C13	118.06 (12)	C12—C13—H13	122.00
C9—C8—C13	120.51 (13)	N1—C15—H15A	109.00
C8—C9—C10	122.17 (13)	N1—C15—H15B	109.00
C9—C10—C11	116.41 (13)	C16—C15—H15A	109.00
N1—C11—C10	132.87 (13)	C16—C15—H15B	109.00
N1—C11—C12	105.90 (12)	H15A—C15—H15B	108.00
C10—C11—C12	121.23 (13)	O5—C17—H17A	109.00
O2—C12—C11	109.14 (12)	O5—C17—H17B	109.00
O2—C12—C13	127.46 (12)	O5—C17—H17C	109.00
C11—C12—C13	123.39 (12)	H17A—C17—H17B	109.00
C8—C13—C12	116.27 (12)	H17A—C17—H17C	110.00
O2—C14—O3	122.82 (13)	H17B—C17—H17C	109.00

C12—O2—C14—O3	−178.68 (17)	C7—C1—C6—Cl1	−1.0 (2)
C12—O2—C14—N1	1.19 (17)	C1—C2—C3—C4	−1.0 (3)
C14—O2—C12—C11	−0.60 (17)	C2—C3—C4—C5	−0.1 (3)
C14—O2—C12—C13	178.47 (16)	C3—C4—C5—C6	0.9 (3)
C17—O5—C16—O4	−0.4 (2)	C4—C5—C6—Cl1	−175.19 (15)
C17—O5—C16—C15	179.18 (14)	C4—C5—C6—C1	−0.6 (3)
C11—N1—C15—C16	63.7 (2)	O1—C7—C8—C13	−24.5 (2)
C14—N1—C15—C16	−126.64 (15)	C1—C7—C8—C13	156.98 (14)
C15—N1—C14—O3	7.3 (3)	C1—C7—C8—C9	−25.5 (2)
C11—N1—C14—O2	−1.35 (18)	O1—C7—C8—C9	153.09 (16)
C15—N1—C14—O2	−172.60 (14)	C7—C8—C13—C12	178.70 (14)
C15—N1—C11—C12	171.82 (15)	C9—C8—C13—C12	1.1 (2)
C14—N1—C11—C10	−178.64 (17)	C7—C8—C9—C10	−177.46 (15)
C15—N1—C11—C10	−7.8 (3)	C13—C8—C9—C10	0.1 (2)
C14—N1—C11—C12	0.96 (17)	C8—C9—C10—C11	−1.0 (2)
C11—N1—C14—O3	178.51 (18)	C9—C10—C11—N1	−179.59 (16)
C2—C1—C7—C8	126.42 (15)	C9—C10—C11—C12	0.9 (2)
C2—C1—C6—Cl1	174.09 (12)	N1—C11—C12—C13	−179.33 (15)
C7—C1—C2—C3	176.53 (15)	C10—C11—C12—O2	179.44 (14)
C7—C1—C6—C5	−175.48 (15)	N1—C11—C12—O2	−0.21 (17)
C2—C1—C7—O1	−52.2 (2)	C10—C11—C12—C13	0.3 (2)
C6—C1—C2—C3	1.2 (2)	C11—C12—C13—C8	−1.3 (2)
C6—C1—C7—C8	−58.6 (2)	O2—C12—C13—C8	179.74 (14)
C2—C1—C6—C5	−0.4 (2)	N1—C15—C16—O5	−171.57 (12)
C6—C1—C7—O1	122.87 (17)	N1—C15—C16—O4	8.0 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O3	0.97	2.55	2.9350 (19)	104
C17—H17A···O4	0.96	2.28	2.697 (2)	106

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