Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027984/tk6290sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027984/tk6290Isup2.hkl |
CCDC reference: 287740
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.075
- 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 .. 7.42 su
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C1 .. 6.66 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C4 .. 6.15 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.64 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 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 4 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
2-Oxazolidinone (0.44 g, 5 mmol), prepared according to the procedure of Homeyer (1946), and triethylamine (0.72 g, 7 mmol) were dissolved in dichloromethane (20 ml) with stirring. Benzoyl chloride (0.85 g, 6 mmol) was added dropwise to the mixture in an ice bath. The mixture was stirred at 273 K for 10 h, washed with water three times and then dried in vacuo to give a solid (yield 90.1%, 0.86 g), which was then recrystallized from ethanol to give colourless blocks (m.p. 447–448 K).
H atoms were included in the riding-model approximation, with C—H = 0.97 and 0.98 Å for methylene and aromatic H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) of the parent atom. Please check changes to text.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku & Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 [reference is for SIR97; which was used?] (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkins et al., 1996); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: CrystalStructure.
C10H9NO3 | F(000) = 400 |
Mr = 191.19 | Dx = 1.418 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ybc | Cell parameters from 6957 reflections |
a = 13.305 (7) Å | θ = 3.2–27.5° |
b = 5.676 (4) Å | µ = 0.11 mm−1 |
c = 12.455 (6) Å | T = 296 K |
β = 107.784 (16)° | Block, colorless |
V = 895.7 (9) Å3 | 0.24 × 0.23 × 0.15 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 1403 reflections with F2 > 2σ(F2) |
Detector resolution: 10.0 pixels mm-1 | Rint = 0.026 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −16→17 |
Tmin = 0.952, Tmax = 0.984 | k = −7→7 |
8404 measured reflections | l = −16→16 |
2051 independent reflections |
Refinement on F2 | w = 1/[0.0002Fo2 + σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.034 | (Δ/σ)max < 0.001 |
wR(F2) = 0.075 | Δρmax = 0.22 e Å−3 |
S = 1.04 | Δρmin = −0.14 e Å−3 |
2051 reflections | Extinction correction: Larson (1970) Crystallographic Computing eq. 22 |
126 parameters | Extinction coefficient: 195 (15) |
H-atom parameters constrained |
C10H9NO3 | V = 895.7 (9) Å3 |
Mr = 191.19 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.305 (7) Å | µ = 0.11 mm−1 |
b = 5.676 (4) Å | T = 296 K |
c = 12.455 (6) Å | 0.24 × 0.23 × 0.15 mm |
β = 107.784 (16)° |
Rigaku R-AXIS RAPID diffractometer | 2051 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1403 reflections with F2 > 2σ(F2) |
Tmin = 0.952, Tmax = 0.984 | Rint = 0.026 |
8404 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 126 parameters |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.22 e Å−3 |
2051 reflections | Δρmin = −0.14 e Å−3 |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
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). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.38119 (6) | 0.09210 (18) | 0.33440 (6) | 0.0678 (2) | |
O2 | 0.44947 (6) | 0.06480 (16) | 0.19229 (6) | 0.0603 (2) | |
O3 | 0.23169 (8) | 0.66383 (18) | 0.15404 (8) | 0.0768 (3) | |
N1 | 0.32096 (6) | 0.32447 (17) | 0.17355 (6) | 0.0435 (2) | |
C1 | 0.38231 (8) | 0.1530 (2) | 0.24286 (9) | 0.0490 (3) | |
C2 | 0.43233 (10) | 0.1727 (2) | 0.08286 (10) | 0.0613 (3) | |
C3 | 0.36198 (9) | 0.3813 (2) | 0.08050 (9) | 0.0525 (3) | |
C4 | 0.25117 (9) | 0.4747 (2) | 0.20166 (9) | 0.0473 (3) | |
C5 | 0.19673 (8) | 0.3949 (2) | 0.28289 (8) | 0.0410 (2) | |
C6 | 0.14438 (8) | 0.1810 (2) | 0.27013 (9) | 0.0461 (3) | |
C7 | 0.08432 (9) | 0.1242 (2) | 0.33910 (10) | 0.0539 (3) | |
C8 | 0.07932 (9) | 0.2760 (2) | 0.42380 (10) | 0.0585 (3) | |
C9 | 0.13266 (9) | 0.4864 (2) | 0.43830 (10) | 0.0584 (3) | |
C10 | 0.19014 (9) | 0.5492 (2) | 0.36696 (9) | 0.0494 (3) | |
H21 | 0.4988 | 0.2219 | 0.0732 | 0.075* | |
H22 | 0.3976 | 0.0623 | 0.0237 | 0.075* | |
H31 | 0.3057 | 0.3929 | 0.0096 | 0.062* | |
H32 | 0.4021 | 0.5269 | 0.0943 | 0.062* | |
H6 | 0.1507 | 0.0707 | 0.2120 | 0.055* | |
H7 | 0.0447 | −0.0240 | 0.3278 | 0.064* | |
H8 | 0.0379 | 0.2340 | 0.4740 | 0.072* | |
H9 | 0.1295 | 0.5929 | 0.4991 | 0.071* | |
H10 | 0.2272 | 0.7006 | 0.3761 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0672 (5) | 0.0845 (7) | 0.0541 (5) | 0.0314 (5) | 0.0217 (4) | 0.0229 (4) |
O2 | 0.0539 (4) | 0.0687 (6) | 0.0620 (5) | 0.0177 (4) | 0.0230 (4) | 0.0003 (4) |
O3 | 0.0990 (7) | 0.0569 (6) | 0.0830 (6) | 0.0277 (5) | 0.0404 (5) | 0.0252 (5) |
N1 | 0.0429 (4) | 0.0481 (5) | 0.0390 (4) | 0.0066 (4) | 0.0117 (3) | 0.0024 (4) |
C1 | 0.0432 (5) | 0.0534 (7) | 0.0491 (6) | 0.0092 (5) | 0.0122 (4) | −0.0002 (5) |
C2 | 0.0546 (6) | 0.0806 (9) | 0.0515 (6) | −0.0013 (6) | 0.0206 (5) | −0.0123 (6) |
C3 | 0.0482 (6) | 0.0677 (9) | 0.0419 (5) | −0.0041 (5) | 0.0143 (4) | 0.0008 (5) |
C4 | 0.0488 (5) | 0.0442 (7) | 0.0453 (5) | 0.0076 (5) | 0.0089 (4) | 0.0016 (5) |
C5 | 0.0389 (5) | 0.0401 (6) | 0.0407 (5) | 0.0111 (4) | 0.0073 (4) | −0.0004 (4) |
C6 | 0.0460 (5) | 0.0436 (7) | 0.0461 (5) | 0.0069 (5) | 0.0099 (4) | −0.0068 (5) |
C7 | 0.0448 (5) | 0.0502 (8) | 0.0642 (7) | 0.0029 (5) | 0.0130 (5) | 0.0009 (6) |
C8 | 0.0524 (6) | 0.0680 (9) | 0.0586 (7) | 0.0135 (6) | 0.0221 (5) | 0.0056 (6) |
C9 | 0.0617 (7) | 0.0641 (9) | 0.0500 (6) | 0.0166 (6) | 0.0178 (5) | −0.0105 (6) |
C10 | 0.0498 (5) | 0.0419 (7) | 0.0519 (6) | 0.0077 (5) | 0.0086 (5) | −0.0073 (5) |
O1—C1 | 1.1958 (15) | C7—C8 | 1.3793 (18) |
O2—C1 | 1.3377 (15) | C8—C9 | 1.3726 (19) |
O2—C2 | 1.4472 (15) | C9—C10 | 1.3844 (19) |
O3—C4 | 1.2156 (15) | C2—H21 | 0.970 |
N1—C1 | 1.3888 (14) | C2—H22 | 0.970 |
N1—C3 | 1.4600 (16) | C3—H31 | 0.970 |
N1—C4 | 1.3822 (16) | C3—H32 | 0.970 |
C2—C3 | 1.5044 (19) | C6—H6 | 0.980 |
C4—C5 | 1.4835 (17) | C7—H7 | 0.980 |
C5—C6 | 1.3845 (16) | C8—H8 | 0.980 |
C5—C10 | 1.3882 (16) | C9—H9 | 0.980 |
C6—C7 | 1.3783 (18) | C10—H10 | 0.980 |
O1···O2 | 3.5838 (13) | H21···H10 | 3.506 |
O1···O3 | 3.4904 (12) | H22···O1 | 3.023 |
O1···C2 | 3.3652 (16) | H22···C2 | 3.240 |
O1···C2 | 3.2459 (15) | H22···C5 | 3.361 |
O1···C3 | 3.4669 (14) | H22···C9 | 3.368 |
O1···C3 | 3.1563 (15) | H22···C10 | 2.922 |
O2···O1 | 3.5838 (13) | H22···H21 | 2.641 |
O2···O2 | 3.2785 (12) | H22···H22 | 3.044 |
O2···O2 | 3.2785 (12) | H22···H32 | 3.159 |
O2···O3 | 3.6000 (13) | H22···H9 | 3.595 |
O2···N1 | 3.2962 (11) | H22···H10 | 2.863 |
O2···C1 | 3.1657 (14) | H31···O1 | 2.668 |
O2···C2 | 3.5469 (15) | H31···C5 | 3.200 |
O2···C3 | 3.3241 (12) | H31···C6 | 3.125 |
O3···O1 | 3.4904 (12) | H31···C7 | 3.062 |
O3···O2 | 3.6000 (13) | H31···C8 | 3.028 |
O3···C1 | 3.4050 (15) | H31···C9 | 3.078 |
O3···C9 | 3.2764 (15) | H31···C10 | 3.186 |
N1···O2 | 3.2962 (11) | H31···H7 | 3.597 |
C1···O2 | 3.1657 (14) | H31···H8 | 3.527 |
C1···O3 | 3.4050 (15) | H31···H9 | 3.596 |
C2···O1 | 3.3652 (16) | H31···H10 | 2.849 |
C2···O1 | 3.2459 (15) | H32···O1 | 2.771 |
C2···O2 | 3.5469 (15) | H32···O1 | 3.234 |
C3···O1 | 3.4669 (14) | H32···O2 | 3.277 |
C3···O1 | 3.1563 (15) | H32···O2 | 2.794 |
C3···O2 | 3.3241 (12) | H32···C1 | 3.050 |
C7···C10 | 3.5295 (17) | H32···H21 | 3.130 |
C9···O3 | 3.2764 (15) | H32···H22 | 3.159 |
C10···C7 | 3.5295 (17) | H32···H10 | 3.365 |
O1···H21 | 2.677 | H6···O3 | 2.737 |
O1···H21 | 3.093 | H6···C8 | 3.444 |
O1···H22 | 3.023 | H6···C8 | 3.530 |
O1···H31 | 2.668 | H6···C9 | 3.359 |
O1···H32 | 2.771 | H6···C10 | 3.485 |
O1···H32 | 3.234 | H6···H7 | 3.392 |
O1···H10 | 3.171 | H6···H8 | 3.430 |
O2···H21 | 3.401 | H6···H8 | 3.091 |
O2···H32 | 3.277 | H6···H9 | 2.741 |
O2···H32 | 2.794 | H6···H10 | 2.891 |
O3···H6 | 2.737 | H7···C5 | 3.118 |
O3···H8 | 3.475 | H7···C6 | 2.957 |
O3···H9 | 2.424 | H7···C7 | 3.013 |
O3···H10 | 3.528 | H7···C8 | 3.267 |
C1···H21 | 3.395 | H7···C9 | 3.163 |
C1···H32 | 3.050 | H7···C9 | 3.432 |
C2···H21 | 3.274 | H7···C10 | 3.046 |
C2···H22 | 3.240 | H7···C10 | 3.345 |
C3···H10 | 3.541 | H7···H31 | 3.597 |
C4···H8 | 3.547 | H7···H6 | 3.392 |
C4···H9 | 3.538 | H7···H7 | 3.438 |
C5···H22 | 3.361 | H7···H7 | 3.438 |
C5···H31 | 3.200 | H7···H8 | 3.222 |
C5···H7 | 3.118 | H7···H9 | 3.014 |
C6···H31 | 3.125 | H7···H10 | 2.795 |
C6···H7 | 2.957 | H8···O3 | 3.475 |
C6···H8 | 3.557 | H8···C4 | 3.547 |
C6···H10 | 3.083 | H8···C6 | 3.557 |
C7···H31 | 3.062 | H8···C9 | 3.222 |
C7···H7 | 3.013 | H8···H31 | 3.527 |
C7···H9 | 3.563 | H8···H6 | 3.430 |
C7···H10 | 3.012 | H8···H6 | 3.091 |
C8···H31 | 3.028 | H8···H7 | 3.222 |
C8···H6 | 3.444 | H8···H8 | 2.982 |
C8···H6 | 3.530 | H8···H8 | 3.311 |
C8···H7 | 3.267 | H8···H9 | 2.549 |
C8···H9 | 3.290 | H9···O3 | 2.424 |
C9···H22 | 3.368 | H9···C4 | 3.538 |
C9···H31 | 3.078 | H9···C7 | 3.563 |
C9···H6 | 3.359 | H9···C8 | 3.290 |
C9···H7 | 3.163 | H9···H22 | 3.595 |
C9···H7 | 3.432 | H9···H31 | 3.596 |
C9···H8 | 3.222 | H9···H6 | 2.741 |
C10···H22 | 2.922 | H9···H7 | 3.014 |
C10···H31 | 3.186 | H9···H8 | 2.549 |
C10···H6 | 3.485 | H10···O1 | 3.171 |
C10···H7 | 3.046 | H10···O3 | 3.528 |
C10···H7 | 3.345 | H10···C3 | 3.541 |
H21···O1 | 2.677 | H10···C6 | 3.083 |
H21···O1 | 3.093 | H10···C7 | 3.012 |
H21···O2 | 3.401 | H10···H21 | 3.506 |
H21···C1 | 3.395 | H10···H22 | 2.863 |
H21···C2 | 3.274 | H10···H31 | 2.849 |
H21···H21 | 3.115 | H10···H32 | 3.365 |
H21···H22 | 2.641 | H10···H6 | 2.891 |
H21···H32 | 3.130 | H10···H7 | 2.795 |
C1—O2—C2 | 110.45 (9) | O2—C2—H21 | 110.6 |
C1—N1—C3 | 110.92 (9) | O2—C2—H22 | 110.1 |
C1—N1—C4 | 126.00 (9) | C3—C2—H21 | 110.9 |
C3—N1—C4 | 120.51 (9) | C3—C2—H22 | 110.1 |
O1—C1—O2 | 123.06 (10) | H21—C2—H22 | 109.5 |
O1—C1—N1 | 128.25 (11) | N1—C3—H31 | 111.5 |
O2—C1—N1 | 108.66 (9) | N1—C3—H32 | 111.5 |
O2—C2—C3 | 105.64 (10) | C2—C3—H31 | 111.9 |
N1—C3—C2 | 101.05 (9) | C2—C3—H32 | 111.2 |
O3—C4—N1 | 118.74 (12) | H31—C3—H32 | 109.5 |
O3—C4—C5 | 121.77 (11) | C5—C6—H6 | 119.5 |
N1—C4—C5 | 119.36 (10) | C7—C6—H6 | 120.5 |
C4—C5—C6 | 121.51 (10) | C6—C7—H7 | 120.0 |
C4—C5—C10 | 118.58 (10) | C8—C7—H7 | 119.8 |
C6—C5—C10 | 119.63 (11) | C7—C8—H8 | 120.2 |
C5—C6—C7 | 120.04 (11) | C9—C8—H8 | 119.8 |
C6—C7—C8 | 120.21 (11) | C8—C9—H9 | 119.7 |
C7—C8—C9 | 120.02 (12) | C10—C9—H9 | 120.0 |
C8—C9—C10 | 120.29 (12) | C5—C10—H10 | 119.7 |
C5—C10—C9 | 119.75 (11) | C9—C10—H10 | 120.5 |
C1—O2—C2—C3 | 12.57 (12) | O2—C2—C3—N1 | −17.14 (10) |
C2—O2—C1—O1 | −179.78 (11) | O3—C4—C5—C6 | 125.27 (12) |
C2—O2—C1—N1 | −1.83 (12) | O3—C4—C5—C10 | −48.55 (13) |
C1—N1—C3—C2 | 17.03 (11) | N1—C4—C5—C6 | −50.48 (13) |
C3—N1—C1—O1 | 167.52 (11) | N1—C4—C5—C10 | 135.70 (10) |
C3—N1—C1—O2 | −10.30 (12) | C4—C5—C6—C7 | −172.40 (9) |
C1—N1—C4—O3 | 153.89 (10) | C4—C5—C10—C9 | 174.91 (9) |
C1—N1—C4—C5 | −30.23 (15) | C6—C5—C10—C9 | 0.97 (15) |
C4—N1—C1—O1 | 5.80 (19) | C10—C5—C6—C7 | 1.36 (14) |
C4—N1—C1—O2 | −172.02 (9) | C5—C6—C7—C8 | −2.46 (15) |
C3—N1—C4—O3 | −6.23 (14) | C6—C7—C8—C9 | 1.22 (16) |
C3—N1—C4—C5 | 169.65 (8) | C7—C8—C9—C10 | 1.13 (16) |
C4—N1—C3—C2 | 179.90 (8) | C8—C9—C10—C5 | −2.22 (16) |
Experimental details
Crystal data | |
Chemical formula | C10H9NO3 |
Mr | 191.19 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 13.305 (7), 5.676 (4), 12.455 (6) |
β (°) | 107.784 (16) |
V (Å3) | 895.7 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.24 × 0.23 × 0.15 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.952, 0.984 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 8404, 2051, 1403 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.075, 1.04 |
No. of reflections | 2051 |
No. of parameters | 126 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.14 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku & Rigaku/MSC, 2004), SHELXS97 [reference is for SIR97; which was used?] (Altomare et al., 1999), CRYSTALS (Watkins et al., 1996), WinGX (Farrugia, 1999), CrystalStructure.
O1—C1 | 1.1958 (15) | C4—C5 | 1.4835 (17) |
O2—C1 | 1.3377 (15) | C5—C6 | 1.3845 (16) |
O2—C2 | 1.4472 (15) | C5—C10 | 1.3882 (16) |
O3—C4 | 1.2156 (15) | C6—C7 | 1.3783 (18) |
N1—C1 | 1.3888 (14) | C7—C8 | 1.3793 (18) |
N1—C3 | 1.4600 (16) | C8—C9 | 1.3726 (19) |
N1—C4 | 1.3822 (16) | C9—C10 | 1.3844 (19) |
C2—C3 | 1.5044 (19) | ||
C1—O2—C2 | 110.45 (9) | O2—C1—N1 | 108.66 (9) |
C1—N1—C3 | 110.92 (9) | O2—C2—C3 | 105.64 (10) |
C1—N1—C4 | 126.00 (9) | N1—C3—C2 | 101.05 (9) |
C3—N1—C4 | 120.51 (9) | O3—C4—N1 | 118.74 (12) |
O1—C1—O2 | 123.06 (10) | O3—C4—C5 | 121.77 (11) |
O1—C1—N1 | 128.25 (11) | N1—C4—C5 | 119.36 (10) |
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Oxazolidinone derivatives have a high potential for biological activity, e.g. they have been widely used as pesticides and fungicides (Edwin & Bing, 1963). As a continuation of our work on the structure–activity relationship of thiazolidinone derivatives, the structure of a colourless crystalline compound, (I), which was the product of the condensation reaction between benzoyl chloride and 2-oxazolidinone, was determined.
The molecular structure of (I) (Fig. 1 and Table 1) establishes the molecular connectivity. The molecule is non-planar, as seen in the C1/N1/C4/C5 and N1/C4/C5/C6 torsion angles of −30.23 (15) and −50.48 (13)°, respectively. The most notable feature of (I) is that the average (O═C)—N bond length of 1.4211 (16) Å is longer than the C—N single-bond length of the typical acylamine group.