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
CCDC reference: 610940
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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
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) Å3 | 0.42 × 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-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 top
Refinement on F2 | H-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 = 1.00 | Δρmax = 0.41 e Å−3 |
3579 reflections | Δρmin = −0.34 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) | | |