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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].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806014735/ya2007sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806014735/ya2007Isup2.hkl
Contains datablock I

CCDC reference: 610940

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

Computing details top

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 top
Crystal data top
C15H15Cl2NO4F(000) = 712
Mr = 344.19Dx = 1.455 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybcCell parameters from 11678 reflections
a = 10.131 (4) Åθ = 3.3–27.5°
b = 15.345 (8) ŵ = 0.43 mm1
c = 10.505 (4) ÅT = 296 K
β = 105.846 (16)°Chunk, colorless
V = 1571.1 (12) Å30.42 × 0.36 × 0.30 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2113 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.040
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 130
Tmin = 0.822, Tmax = 0.879k = 1919
16981 measured reflectionsl = 1313
3579 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039 w = 1/[0.77σ(Fo2)]/(4Fo2)
wR(F2) = 0.100(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.41 e Å3
3579 reflectionsΔρmin = 0.34 e Å3
200 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.23350 (6)0.03579 (4)0.29231 (6)0.06915 (19)
Cl20.48355 (6)0.05429 (4)0.29066 (6)0.0753 (2)
O10.20979 (13)0.06789 (10)0.53671 (13)0.0621 (4)
O20.11496 (16)0.25781 (11)0.36991 (18)0.0851 (5)
O30.06263 (17)0.27431 (12)0.2849 (2)0.0953 (6)
O40.69686 (12)0.37293 (9)0.61830 (12)0.0571 (4)
N10.05068 (14)0.15934 (10)0.42283 (14)0.0477 (4)
C10.27287 (18)0.14195 (12)0.36444 (18)0.0451 (5)
C20.3125 (2)0.06582 (12)0.2911 (2)0.0532 (6)
C30.2279 (2)0.13606 (13)0.2152 (2)0.0619 (6)
C40.17731 (18)0.11970 (12)0.44830 (19)0.0453 (5)
C50.04418 (19)0.13247 (13)0.4985 (2)0.0593 (6)
C60.1594 (2)0.1955 (2)0.4503 (2)0.0961 (10)
C70.0061 (2)0.23437 (14)0.3514 (2)0.0647 (7)
C80.38098 (18)0.20647 (12)0.43039 (18)0.0429 (5)
C90.4717 (2)0.18726 (12)0.55224 (19)0.0504 (5)
C100.5737 (2)0.24399 (12)0.61236 (19)0.0525 (6)
C110.58968 (19)0.32202 (12)0.55235 (19)0.0457 (5)
C120.4995 (2)0.34242 (12)0.4306 (2)0.0516 (5)
C130.3960 (2)0.28533 (12)0.37279 (19)0.0508 (5)
C140.7211 (2)0.45198 (13)0.5589 (2)0.0667 (7)
C150.8399 (2)0.49670 (19)0.6481 (2)0.0958 (10)
H310.13220.12540.17000.074*
H320.26680.17540.16280.074*
H510.07500.07300.47810.074*
H520.00250.13800.59300.074*
H620.17880.22480.52500.119*
H610.24120.16560.39960.119*
H90.46310.13470.59330.061*
H100.63260.23020.69460.062*
H120.50880.39470.38920.062*
H130.33490.30000.29220.060*
H1410.74160.43960.47580.081*
H1420.64050.48900.54260.081*
H1530.85720.55050.60890.111*
H1510.81970.50850.73050.111*
H1520.91960.46010.66370.111*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0772 (4)0.0524 (3)0.0853 (4)0.0179 (2)0.0349 (3)0.0084 (2)
Cl20.0714 (3)0.0705 (4)0.1012 (4)0.0143 (2)0.0524 (3)0.0233 (3)
O10.0582 (8)0.0652 (9)0.0690 (9)0.0133 (7)0.0279 (7)0.0256 (8)
O20.0614 (10)0.0708 (11)0.1175 (14)0.0268 (8)0.0149 (9)0.0063 (10)
O30.0747 (11)0.0741 (12)0.1309 (15)0.0048 (9)0.0174 (11)0.0536 (11)
O40.0597 (8)0.0492 (8)0.0607 (8)0.0109 (7)0.0136 (7)0.0009 (7)
N10.0452 (8)0.0437 (9)0.0558 (9)0.0038 (7)0.0165 (7)0.0015 (7)
C10.0472 (10)0.0428 (11)0.0478 (10)0.0013 (8)0.0170 (9)0.0057 (9)
C20.0583 (12)0.0494 (12)0.0585 (12)0.0122 (10)0.0271 (10)0.0046 (10)
C30.0713 (14)0.0649 (15)0.0486 (11)0.0145 (11)0.0147 (11)0.0043 (11)
C40.0457 (10)0.0397 (11)0.0515 (11)0.0006 (8)0.0151 (9)0.0038 (9)
C50.0530 (11)0.0670 (15)0.0658 (13)0.0037 (10)0.0294 (11)0.0041 (11)
C60.0722 (16)0.119 (2)0.105 (2)0.0337 (17)0.0372 (16)0.018 (2)
C70.0582 (13)0.0467 (13)0.0805 (15)0.0028 (11)0.0042 (12)0.0065 (12)
C80.0467 (10)0.0407 (11)0.0456 (10)0.0016 (8)0.0201 (8)0.0011 (9)
C90.0595 (11)0.0401 (11)0.0546 (11)0.0004 (9)0.0208 (10)0.0076 (9)
C100.0594 (12)0.0495 (12)0.0470 (11)0.0005 (10)0.0115 (9)0.0041 (10)
C110.0481 (10)0.0424 (11)0.0519 (11)0.0003 (9)0.0226 (9)0.0050 (9)
C120.0595 (11)0.0408 (11)0.0572 (12)0.0035 (9)0.0202 (10)0.0065 (9)
C130.0556 (11)0.0491 (12)0.0468 (10)0.0022 (9)0.0123 (9)0.0090 (10)
C140.0672 (14)0.0569 (14)0.0771 (15)0.0133 (11)0.0219 (12)0.0021 (12)
C150.092 (2)0.0764 (19)0.108 (2)0.0324 (16)0.0097 (16)0.0025 (17)
Geometric parameters (Å, º) top
Cl1—C21.754 (2)C10—C111.383 (2)
Cl2—C21.744 (2)C11—C121.389 (2)
O1—C41.198 (2)C12—C131.374 (2)
O2—C61.428 (3)C14—C151.478 (3)
O2—C71.342 (3)C3—H310.970
O3—C71.188 (3)C3—H320.970
O4—C111.363 (2)C5—H510.970
O4—C141.416 (2)C5—H520.970
N1—C41.378 (2)C6—H620.970
N1—C51.464 (2)C6—H610.970
N1—C71.381 (2)C9—H90.930
C1—C21.512 (2)C10—H100.930
C1—C31.511 (2)C12—H120.930
C1—C41.515 (2)C13—H130.930
C1—C81.498 (2)C14—H1410.970
C2—C31.469 (2)C14—H1420.970
C5—C61.494 (3)C15—H1530.960
C8—C91.388 (2)C15—H1510.960
C8—C131.380 (2)C15—H1520.960
C9—C101.367 (2)
C6—O2—C7110.75 (19)O4—C14—C15109.11 (18)
C11—O4—C14118.47 (14)C1—C3—H31119.8
C4—N1—C5118.98 (15)C1—C3—H32119.9
C4—N1—C7128.49 (18)C2—C3—H31119.9
C5—N1—C7111.34 (17)C2—C3—H32119.8
C2—C1—C358.14 (13)H31—C3—H32109.4
C2—C1—C4114.99 (16)N1—C5—H51111.4
C2—C1—C8118.93 (16)N1—C5—H52111.3
C3—C1—C4122.02 (15)C6—C5—H51111.1
C3—C1—C8119.63 (17)C6—C5—H52111.8
C4—C1—C8112.49 (15)H51—C5—H52109.4
Cl1—C2—Cl2111.43 (11)O2—C6—H62109.5
Cl1—C2—C1119.87 (16)O2—C6—H61110.6
Cl1—C2—C3117.17 (14)C5—C6—H62109.8
Cl2—C2—C1118.80 (13)C5—C6—H61110.6
Cl2—C2—C3120.38 (16)H62—C6—H61109.4
C1—C2—C360.87 (13)C8—C9—H9119.3
C1—C3—C260.99 (13)C10—C9—H9119.5
O1—C4—N1119.16 (19)C9—C10—H10119.7
O1—C4—C1121.08 (16)C11—C10—H10119.7
N1—C4—C1119.76 (16)C11—C12—H12120.0
N1—C5—C6101.64 (18)C13—C12—H12120.4
O2—C6—C5106.9 (2)C8—C13—H13119.1
O2—C7—O3123.6 (2)C12—C13—H13119.1
O2—C7—N1108.7 (2)O4—C14—H141109.5
O3—C7—N1127.7 (2)O4—C14—H142109.9
C1—C8—C9120.14 (16)C15—C14—H141108.9
C1—C8—C13122.06 (15)C15—C14—H142109.9
C9—C8—C13117.78 (16)H141—C14—H142109.4
C8—C9—C10121.16 (18)C14—C15—H153109.9
C9—C10—C11120.56 (16)C14—C15—H151108.8
O4—C11—C10116.13 (15)C14—C15—H152109.7
O4—C11—C12124.83 (18)H153—C15—H151109.5
C10—C11—C12119.03 (17)H153—C15—H152109.5
C11—C12—C13119.60 (18)H151—C15—H152109.5
C8—C13—C12121.83 (16)
C6—O2—C7—O3177.8 (2)C8—C1—C2—Cl22.0 (2)
C6—O2—C7—N13.1 (2)C8—C1—C2—C3108.8 (2)
C7—O2—C6—C57.1 (2)C3—C1—C4—O1126.5 (2)
C11—O4—C14—C15179.1 (2)C3—C1—C4—N153.4 (2)
C14—O4—C11—C10177.61 (19)C4—C1—C3—C2101.4 (2)
C14—O4—C11—C121.1 (3)C3—C1—C8—C9147.2 (2)
C4—N1—C5—C6174.97 (17)C3—C1—C8—C1331.7 (2)
C5—N1—C4—O14.2 (2)C8—C1—C3—C2107.57 (19)
C5—N1—C4—C1175.64 (15)C4—C1—C8—C959.2 (2)
C4—N1—C7—O2169.64 (17)C4—C1—C8—C13121.9 (2)
C4—N1—C7—O39.5 (3)C8—C1—C4—O180.6 (2)
C7—N1—C4—O1162.15 (19)C8—C1—C4—N199.50 (18)
C7—N1—C4—C118.0 (2)Cl1—C2—C3—C1110.79 (18)
C5—N1—C7—O22.4 (2)Cl2—C2—C3—C1108.22 (17)
C5—N1—C7—O3176.7 (2)N1—C5—C6—O27.8 (2)
C7—N1—C5—C66.4 (2)C1—C8—C9—C10178.0 (2)
C3—C1—C2—Cl1106.43 (17)C1—C8—C13—C12176.7 (2)
C3—C1—C2—Cl2110.75 (18)C9—C8—C13—C122.1 (3)
C2—C1—C4—O159.8 (2)C13—C8—C9—C100.9 (3)
C2—C1—C4—N1120.09 (18)C8—C9—C10—C110.5 (3)
C4—C1—C2—Cl17.1 (2)C9—C10—C11—O4178.13 (19)
C4—C1—C2—Cl2135.73 (14)C9—C10—C11—C120.7 (3)
C4—C1—C2—C3113.52 (17)O4—C11—C12—C13179.2 (2)
C2—C1—C8—C979.5 (2)C10—C11—C12—C130.5 (3)
C2—C1—C8—C1399.4 (2)C11—C12—C13—C81.9 (3)
C8—C1—C2—Cl1144.81 (14)
 

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