3-[2,2-Dichloro-1-(4-ethoxy­phen­yl)cyclo­propane­carbon­yl]oxazolidin-2-one

The title compound, C₁₅H₁₅Cl₂NO₄, a cyclo­propane derivative related to the insecticide cyclo­prothrin, was prepared from oxazolidin-2-one and 2,2-dichloro-1-(4-ethoxy­phen­yl)cyclo­propane­carbonyl chloride. The five-membered oxazolidine ring is planar to within 0.045 Å; the cyclo­propane ring plane forms approximately equal dihedral angles with the mean planes of the oxazolidine and benzene rings [62.7 (4) and 61.6 (4)°, respectively].

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.100
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C7      ..       5.77 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6

   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

   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
   0 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: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

3-[2,2-Dichloro-1-(4-ethoxyphenyl)cyclopropanecarbonyl]oxazolidin-2-one

Crystal data

C15H15Cl2NO4	F(000) = 712
Mr = 344.19	Dx = 1.455 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 11678 reflections
a = 10.131 (4) Å	θ = 3.3–27.5°
b = 15.345 (8) Å	µ = 0.43 mm^−1
c = 10.505 (4) Å	T = 296 K
β = 105.846 (16)°	Chunk, colorless
V = 1571.1 (12) Å^3	0.42 × 0.36 × 0.30 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2113 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.040
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→0
Tmin = 0.822, Tmax = 0.879	k = −19→19
16981 measured reflections	l = −13→13
3579 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[0.77σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.100	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.41 e Å^−3
3579 reflections	Δρmin = −0.34 e Å^−3
200 parameters

Special details

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
Cl1	0.23350 (6)	−0.03579 (4)	0.29231 (6)	0.06915 (19)
Cl2	0.48355 (6)	0.05429 (4)	0.29066 (6)	0.0753 (2)
O1	0.20979 (13)	0.06789 (10)	0.53671 (13)	0.0621 (4)
O2	−0.11496 (16)	0.25781 (11)	0.36991 (18)	0.0851 (5)
O3	0.06263 (17)	0.27431 (12)	0.2849 (2)	0.0953 (6)
O4	0.69686 (12)	0.37293 (9)	0.61830 (12)	0.0571 (4)
N1	0.05068 (14)	0.15934 (10)	0.42283 (14)	0.0477 (4)
C1	0.27287 (18)	0.14195 (12)	0.36444 (18)	0.0451 (5)
C2	0.3125 (2)	0.06582 (12)	0.2911 (2)	0.0532 (6)
C3	0.2279 (2)	0.13606 (13)	0.2152 (2)	0.0619 (6)
C4	0.17731 (18)	0.11970 (12)	0.44830 (19)	0.0453 (5)
C5	−0.04418 (19)	0.13247 (13)	0.4985 (2)	0.0593 (6)
C6	−0.1594 (2)	0.1955 (2)	0.4503 (2)	0.0961 (10)
C7	0.0061 (2)	0.23437 (14)	0.3514 (2)	0.0647 (7)
C8	0.38098 (18)	0.20647 (12)	0.43039 (18)	0.0429 (5)
C9	0.4717 (2)	0.18726 (12)	0.55224 (19)	0.0504 (5)
C10	0.5737 (2)	0.24399 (12)	0.61236 (19)	0.0525 (6)
C11	0.58968 (19)	0.32202 (12)	0.55235 (19)	0.0457 (5)
C12	0.4995 (2)	0.34242 (12)	0.4306 (2)	0.0516 (5)
C13	0.3960 (2)	0.28533 (12)	0.37279 (19)	0.0508 (5)
C14	0.7211 (2)	0.45198 (13)	0.5589 (2)	0.0667 (7)
C15	0.8399 (2)	0.49670 (19)	0.6481 (2)	0.0958 (10)
H31	0.1322	0.1254	0.1700	0.074*
H32	0.2668	0.1754	0.1628	0.074*
H51	−0.0750	0.0730	0.4781	0.074*
H52	−0.0025	0.1380	0.5930	0.074*
H62	−0.1788	0.2248	0.5250	0.119*
H61	−0.2412	0.1656	0.3996	0.119*
H9	0.4631	0.1347	0.5933	0.061*
H10	0.6326	0.2302	0.6946	0.062*
H12	0.5088	0.3947	0.3892	0.062*
H13	0.3349	0.3000	0.2922	0.060*
H141	0.7416	0.4396	0.4758	0.081*
H142	0.6405	0.4890	0.5426	0.081*
H153	0.8572	0.5505	0.6089	0.111*
H151	0.8197	0.5085	0.7305	0.111*
H152	0.9196	0.4601	0.6637	0.111*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0772 (4)	0.0524 (3)	0.0853 (4)	−0.0179 (2)	0.0349 (3)	−0.0084 (2)
Cl2	0.0714 (3)	0.0705 (4)	0.1012 (4)	−0.0143 (2)	0.0524 (3)	−0.0233 (3)
O1	0.0582 (8)	0.0652 (9)	0.0690 (9)	0.0133 (7)	0.0279 (7)	0.0256 (8)
O2	0.0614 (10)	0.0708 (11)	0.1175 (14)	0.0268 (8)	0.0149 (9)	0.0063 (10)
O3	0.0747 (11)	0.0741 (12)	0.1309 (15)	0.0048 (9)	0.0174 (11)	0.0536 (11)
O4	0.0597 (8)	0.0492 (8)	0.0607 (8)	−0.0109 (7)	0.0136 (7)	−0.0009 (7)
N1	0.0452 (8)	0.0437 (9)	0.0558 (9)	0.0038 (7)	0.0165 (7)	0.0015 (7)
C1	0.0472 (10)	0.0428 (11)	0.0478 (10)	−0.0013 (8)	0.0170 (9)	0.0057 (9)
C2	0.0583 (12)	0.0494 (12)	0.0585 (12)	−0.0122 (10)	0.0271 (10)	−0.0046 (10)
C3	0.0713 (14)	0.0649 (15)	0.0486 (11)	−0.0145 (11)	0.0147 (11)	0.0043 (11)
C4	0.0457 (10)	0.0397 (11)	0.0515 (11)	−0.0006 (8)	0.0151 (9)	0.0038 (9)
C5	0.0530 (11)	0.0670 (15)	0.0658 (13)	0.0037 (10)	0.0294 (11)	−0.0041 (11)
C6	0.0722 (16)	0.119 (2)	0.105 (2)	0.0337 (17)	0.0372 (16)	0.018 (2)
C7	0.0582 (13)	0.0467 (13)	0.0805 (15)	0.0028 (11)	0.0042 (12)	0.0065 (12)
C8	0.0467 (10)	0.0407 (11)	0.0456 (10)	0.0016 (8)	0.0201 (8)	0.0011 (9)
C9	0.0595 (11)	0.0401 (11)	0.0546 (11)	−0.0004 (9)	0.0208 (10)	0.0076 (9)
C10	0.0594 (12)	0.0495 (12)	0.0470 (11)	−0.0005 (10)	0.0115 (9)	0.0041 (10)
C11	0.0481 (10)	0.0424 (11)	0.0519 (11)	−0.0003 (9)	0.0226 (9)	−0.0050 (9)
C12	0.0595 (11)	0.0408 (11)	0.0572 (12)	−0.0035 (9)	0.0202 (10)	0.0065 (9)
C13	0.0556 (11)	0.0491 (12)	0.0468 (10)	−0.0022 (9)	0.0123 (9)	0.0090 (10)
C14	0.0672 (14)	0.0569 (14)	0.0771 (15)	−0.0133 (11)	0.0219 (12)	0.0021 (12)
C15	0.092 (2)	0.0764 (19)	0.108 (2)	−0.0324 (16)	0.0097 (16)	0.0025 (17)

Geometric parameters (Å, º)

Cl1—C2	1.754 (2)	C10—C11	1.383 (2)
Cl2—C2	1.744 (2)	C11—C12	1.389 (2)
O1—C4	1.198 (2)	C12—C13	1.374 (2)
O2—C6	1.428 (3)	C14—C15	1.478 (3)
O2—C7	1.342 (3)	C3—H31	0.970
O3—C7	1.188 (3)	C3—H32	0.970
O4—C11	1.363 (2)	C5—H51	0.970
O4—C14	1.416 (2)	C5—H52	0.970
N1—C4	1.378 (2)	C6—H62	0.970
N1—C5	1.464 (2)	C6—H61	0.970
N1—C7	1.381 (2)	C9—H9	0.930
C1—C2	1.512 (2)	C10—H10	0.930
C1—C3	1.511 (2)	C12—H12	0.930
C1—C4	1.515 (2)	C13—H13	0.930
C1—C8	1.498 (2)	C14—H141	0.970
C2—C3	1.469 (2)	C14—H142	0.970
C5—C6	1.494 (3)	C15—H153	0.960
C8—C9	1.388 (2)	C15—H151	0.960
C8—C13	1.380 (2)	C15—H152	0.960
C9—C10	1.367 (2)
C6—O2—C7	110.75 (19)	O4—C14—C15	109.11 (18)
C11—O4—C14	118.47 (14)	C1—C3—H31	119.8
C4—N1—C5	118.98 (15)	C1—C3—H32	119.9
C4—N1—C7	128.49 (18)	C2—C3—H31	119.9
C5—N1—C7	111.34 (17)	C2—C3—H32	119.8
C2—C1—C3	58.14 (13)	H31—C3—H32	109.4
C2—C1—C4	114.99 (16)	N1—C5—H51	111.4
C2—C1—C8	118.93 (16)	N1—C5—H52	111.3
C3—C1—C4	122.02 (15)	C6—C5—H51	111.1
C3—C1—C8	119.63 (17)	C6—C5—H52	111.8
C4—C1—C8	112.49 (15)	H51—C5—H52	109.4
Cl1—C2—Cl2	111.43 (11)	O2—C6—H62	109.5
Cl1—C2—C1	119.87 (16)	O2—C6—H61	110.6
Cl1—C2—C3	117.17 (14)	C5—C6—H62	109.8
Cl2—C2—C1	118.80 (13)	C5—C6—H61	110.6
Cl2—C2—C3	120.38 (16)	H62—C6—H61	109.4
C1—C2—C3	60.87 (13)	C8—C9—H9	119.3
C1—C3—C2	60.99 (13)	C10—C9—H9	119.5
O1—C4—N1	119.16 (19)	C9—C10—H10	119.7
O1—C4—C1	121.08 (16)	C11—C10—H10	119.7
N1—C4—C1	119.76 (16)	C11—C12—H12	120.0
N1—C5—C6	101.64 (18)	C13—C12—H12	120.4
O2—C6—C5	106.9 (2)	C8—C13—H13	119.1
O2—C7—O3	123.6 (2)	C12—C13—H13	119.1
O2—C7—N1	108.7 (2)	O4—C14—H141	109.5
O3—C7—N1	127.7 (2)	O4—C14—H142	109.9
C1—C8—C9	120.14 (16)	C15—C14—H141	108.9
C1—C8—C13	122.06 (15)	C15—C14—H142	109.9
C9—C8—C13	117.78 (16)	H141—C14—H142	109.4
C8—C9—C10	121.16 (18)	C14—C15—H153	109.9
C9—C10—C11	120.56 (16)	C14—C15—H151	108.8
O4—C11—C10	116.13 (15)	C14—C15—H152	109.7
O4—C11—C12	124.83 (18)	H153—C15—H151	109.5
C10—C11—C12	119.03 (17)	H153—C15—H152	109.5
C11—C12—C13	119.60 (18)	H151—C15—H152	109.5
C8—C13—C12	121.83 (16)
C6—O2—C7—O3	177.8 (2)	C8—C1—C2—Cl2	2.0 (2)
C6—O2—C7—N1	−3.1 (2)	C8—C1—C2—C3	−108.8 (2)
C7—O2—C6—C5	7.1 (2)	C3—C1—C4—O1	126.5 (2)
C11—O4—C14—C15	179.1 (2)	C3—C1—C4—N1	−53.4 (2)
C14—O4—C11—C10	177.61 (19)	C4—C1—C3—C2	−101.4 (2)
C14—O4—C11—C12	−1.1 (3)	C3—C1—C8—C9	−147.2 (2)
C4—N1—C5—C6	174.97 (17)	C3—C1—C8—C13	31.7 (2)
C5—N1—C4—O1	−4.2 (2)	C8—C1—C3—C2	107.57 (19)
C5—N1—C4—C1	175.64 (15)	C4—C1—C8—C9	59.2 (2)
C4—N1—C7—O2	−169.64 (17)	C4—C1—C8—C13	−121.9 (2)
C4—N1—C7—O3	9.5 (3)	C8—C1—C4—O1	−80.6 (2)
C7—N1—C4—O1	162.15 (19)	C8—C1—C4—N1	99.50 (18)
C7—N1—C4—C1	−18.0 (2)	Cl1—C2—C3—C1	110.79 (18)
C5—N1—C7—O2	−2.4 (2)	Cl2—C2—C3—C1	−108.22 (17)
C5—N1—C7—O3	176.7 (2)	N1—C5—C6—O2	−7.8 (2)
C7—N1—C5—C6	6.4 (2)	C1—C8—C9—C10	178.0 (2)
C3—C1—C2—Cl1	−106.43 (17)	C1—C8—C13—C12	−176.7 (2)
C3—C1—C2—Cl2	110.75 (18)	C9—C8—C13—C12	2.1 (3)
C2—C1—C4—O1	59.8 (2)	C13—C8—C9—C10	−0.9 (3)
C2—C1—C4—N1	−120.09 (18)	C8—C9—C10—C11	−0.5 (3)
C4—C1—C2—Cl1	7.1 (2)	C9—C10—C11—O4	−178.13 (19)
C4—C1—C2—Cl2	−135.73 (14)	C9—C10—C11—C12	0.7 (3)
C4—C1—C2—C3	113.52 (17)	O4—C11—C12—C13	179.2 (2)
C2—C1—C8—C9	−79.5 (2)	C10—C11—C12—C13	0.5 (3)
C2—C1—C8—C13	99.4 (2)	C11—C12—C13—C8	−1.9 (3)
C8—C1—C2—Cl1	144.81 (14)