In the title molecule, C
10H
8ClNO
2, the isoxazole ring shows normal values of bond lengths and angles. The mean planes of the benzene and isoxazole rings make a dihedral angle of 16.3 (2)°. Intermolecular O—H
N hydrogen bonds link the molecules into chains extended along the
b axis. The crystal packing is further stablized by weak C—H
O interactions and van der Waals forces.
Supporting information
CCDC reference: 605032
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.120
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
[3-(4-Chlorophenyl)isoxazol-5-yl]methanol
top
Crystal data top
C10H8ClNO2 | F(000) = 432 |
Mr = 209.62 | Dx = 1.441 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1048 reflections |
a = 12.968 (3) Å | θ = 2.3–22.3° |
b = 9.622 (2) Å | µ = 0.37 mm−1 |
c = 7.8091 (17) Å | T = 291 K |
β = 97.450 (3)° | Block, colourless |
V = 966.2 (4) Å3 | 0.41 × 0.31 × 0.02 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1705 independent reflections |
Radiation source: fine-focus sealed tube | 1526 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→15 |
Tmin = 0.865, Tmax = 0.993 | k = −11→11 |
4917 measured reflections | l = −9→8 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0507P)2 + 0.3104P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max < 0.001 |
1705 reflections | Δρmax = 0.19 e Å−3 |
129 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.024 (3) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) 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 | Uiso*/Ueq | |
Cl1 | 0.57521 (5) | 0.77592 (8) | 0.08499 (11) | 0.0817 (3) | |
O1 | −0.00919 (12) | 0.55841 (15) | 0.2067 (2) | 0.0616 (5) | |
O2 | −0.17983 (13) | 0.84092 (18) | 0.0524 (2) | 0.0649 (5) | |
H2 | −0.1577 | 0.9020 | 0.1207 | 0.097* | |
N1 | 0.09977 (15) | 0.55000 (18) | 0.2140 (3) | 0.0592 (5) | |
C1 | 0.23936 (17) | 0.6945 (2) | 0.1400 (3) | 0.0472 (5) | |
C2 | 0.27415 (19) | 0.8281 (2) | 0.1155 (3) | 0.0596 (6) | |
H2A | 0.2273 | 0.9017 | 0.1093 | 0.072* | |
C3 | 0.3767 (2) | 0.8536 (3) | 0.1001 (3) | 0.0655 (7) | |
H3 | 0.3992 | 0.9439 | 0.0836 | 0.079* | |
C4 | 0.44579 (19) | 0.7453 (3) | 0.1094 (3) | 0.0592 (6) | |
C5 | 0.41388 (19) | 0.6112 (2) | 0.1364 (3) | 0.0606 (6) | |
H5 | 0.4614 | 0.5383 | 0.1445 | 0.073* | |
C6 | 0.31106 (18) | 0.5868 (2) | 0.1510 (3) | 0.0562 (6) | |
H6 | 0.2891 | 0.4965 | 0.1687 | 0.067* | |
C7 | 0.12899 (17) | 0.6683 (2) | 0.1522 (3) | 0.0475 (5) | |
C8 | 0.04223 (18) | 0.7552 (2) | 0.1038 (3) | 0.0497 (5) | |
H8 | 0.0424 | 0.8440 | 0.0568 | 0.060* | |
C9 | −0.04015 (17) | 0.6826 (2) | 0.1400 (3) | 0.0494 (5) | |
C10 | −0.15400 (19) | 0.7105 (2) | 0.1251 (3) | 0.0608 (6) | |
H10A | −0.1910 | 0.6390 | 0.0542 | 0.073* | |
H10B | −0.1762 | 0.7059 | 0.2389 | 0.073* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0590 (4) | 0.0922 (6) | 0.0966 (6) | −0.0123 (3) | 0.0199 (4) | 0.0001 (4) |
O1 | 0.0555 (10) | 0.0458 (9) | 0.0841 (12) | −0.0031 (7) | 0.0114 (8) | 0.0051 (8) |
O2 | 0.0594 (10) | 0.0620 (10) | 0.0705 (11) | 0.0085 (8) | −0.0021 (8) | −0.0046 (8) |
N1 | 0.0540 (11) | 0.0439 (10) | 0.0798 (14) | 0.0026 (8) | 0.0087 (10) | 0.0073 (9) |
C1 | 0.0525 (12) | 0.0459 (11) | 0.0430 (11) | 0.0005 (9) | 0.0055 (9) | 0.0005 (9) |
C2 | 0.0606 (14) | 0.0469 (12) | 0.0706 (16) | 0.0028 (11) | 0.0056 (12) | 0.0093 (11) |
C3 | 0.0659 (16) | 0.0516 (13) | 0.0779 (17) | −0.0109 (12) | 0.0059 (13) | 0.0118 (12) |
C4 | 0.0545 (14) | 0.0695 (15) | 0.0543 (14) | −0.0077 (12) | 0.0091 (11) | 0.0005 (12) |
C5 | 0.0599 (15) | 0.0538 (13) | 0.0691 (16) | 0.0073 (11) | 0.0123 (12) | −0.0036 (12) |
C6 | 0.0591 (14) | 0.0432 (12) | 0.0673 (15) | −0.0011 (10) | 0.0119 (11) | −0.0006 (11) |
C7 | 0.0586 (13) | 0.0391 (11) | 0.0451 (12) | 0.0007 (10) | 0.0076 (9) | −0.0031 (9) |
C8 | 0.0574 (13) | 0.0411 (11) | 0.0506 (12) | 0.0024 (10) | 0.0069 (10) | 0.0024 (9) |
C9 | 0.0570 (13) | 0.0414 (11) | 0.0495 (12) | 0.0018 (10) | 0.0055 (10) | −0.0051 (9) |
C10 | 0.0542 (14) | 0.0582 (14) | 0.0699 (16) | −0.0030 (11) | 0.0074 (12) | −0.0095 (12) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.739 (3) | C3—H3 | 0.9300 |
O1—C9 | 1.344 (3) | C4—C5 | 1.379 (3) |
O1—N1 | 1.409 (2) | C5—C6 | 1.373 (3) |
O2—C10 | 1.400 (3) | C5—H5 | 0.9300 |
O2—H2 | 0.8200 | C6—H6 | 0.9300 |
N1—C7 | 1.311 (3) | C7—C8 | 1.413 (3) |
C1—C2 | 1.384 (3) | C8—C9 | 1.337 (3) |
C1—C6 | 1.388 (3) | C8—H8 | 0.9300 |
C1—C7 | 1.469 (3) | C9—C10 | 1.490 (3) |
C2—C3 | 1.373 (3) | C10—H10A | 0.9700 |
C2—H2A | 0.9300 | C10—H10B | 0.9700 |
C3—C4 | 1.370 (4) | | |
| | | |
C9—O1—N1 | 108.33 (16) | C5—C6—C1 | 121.1 (2) |
C10—O2—H2 | 109.5 | C5—C6—H6 | 119.4 |
C7—N1—O1 | 105.74 (17) | C1—C6—H6 | 119.4 |
C2—C1—C6 | 118.3 (2) | N1—C7—C8 | 110.7 (2) |
C2—C1—C7 | 120.4 (2) | N1—C7—C1 | 120.24 (19) |
C6—C1—C7 | 121.2 (2) | C8—C7—C1 | 129.0 (2) |
C3—C2—C1 | 121.0 (2) | C9—C8—C7 | 105.33 (19) |
C3—C2—H2A | 119.5 | C9—C8—H8 | 127.3 |
C1—C2—H2A | 119.5 | C7—C8—H8 | 127.3 |
C4—C3—C2 | 119.5 (2) | C8—C9—O1 | 109.9 (2) |
C4—C3—H3 | 120.2 | C8—C9—C10 | 134.4 (2) |
C2—C3—H3 | 120.2 | O1—C9—C10 | 115.69 (19) |
C3—C4—C5 | 120.8 (2) | O2—C10—C9 | 112.0 (2) |
C3—C4—Cl1 | 119.9 (2) | O2—C10—H10A | 109.2 |
C5—C4—Cl1 | 119.2 (2) | C9—C10—H10A | 109.2 |
C6—C5—C4 | 119.1 (2) | O2—C10—H10B | 109.2 |
C6—C5—H5 | 120.4 | C9—C10—H10B | 109.2 |
C4—C5—H5 | 120.4 | H10A—C10—H10B | 107.9 |
| | | |
C9—O1—N1—C7 | 0.1 (2) | C2—C1—C7—N1 | −164.3 (2) |
C6—C1—C2—C3 | 0.8 (4) | C6—C1—C7—N1 | 16.3 (3) |
C7—C1—C2—C3 | −178.6 (2) | C2—C1—C7—C8 | 16.2 (3) |
C1—C2—C3—C4 | 0.0 (4) | C6—C1—C7—C8 | −163.2 (2) |
C2—C3—C4—C5 | −0.9 (4) | N1—C7—C8—C9 | 0.0 (3) |
C2—C3—C4—Cl1 | 178.47 (19) | C1—C7—C8—C9 | 179.5 (2) |
C3—C4—C5—C6 | 1.1 (4) | C7—C8—C9—O1 | 0.0 (2) |
Cl1—C4—C5—C6 | −178.30 (18) | C7—C8—C9—C10 | 178.9 (2) |
C4—C5—C6—C1 | −0.3 (4) | N1—O1—C9—C8 | −0.1 (2) |
C2—C1—C6—C5 | −0.6 (4) | N1—O1—C9—C10 | −179.13 (18) |
C7—C1—C6—C5 | 178.7 (2) | C8—C9—C10—O2 | 2.1 (4) |
O1—N1—C7—C8 | 0.0 (2) | O1—C9—C10—O2 | −179.15 (19) |
O1—N1—C7—C1 | −179.62 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N1i | 0.82 | 2.00 | 2.822 (2) | 178 |
C10—H10B···O2ii | 0.97 | 2.50 | 3.432 (3) | 162 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, −y+3/2, z+1/2. |