The crystal structure of the title compound, C
11H
8N
2O
2S, is stabilized by one N—H
N and two C—H
O intermolecular hydrogen bonds and also by three C—H
π interactions. The C—H
O hydrogen bonds generate
R44(26) ring motifs and the N—H
N and one of the C—H
O hydrogen bonds generate
R43(26) ring motifs. The phthalide ring system of the molecule is almost planar and forms a dihedral angle of 74.84 (9)° with the thiazole ring.
Supporting information
CCDC reference: 613850
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.106
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies
outside the range 0.99 <> 1.01
Calculated value of mu = 0.282
Value of mu given = 0.290
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.74 mm
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. CG1 .. 3.12 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. CG1 .. 3.06 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. CG2 .. 2.93 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
3-(thiazol-2-ylamino)isobenzofuran-1(3
H)-one
top
Crystal data top
C11H8N2O2S | F(000) = 960 |
Mr = 232.25 | Dx = 1.416 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2 ab | Cell parameters from 14575 reflections |
a = 14.291 (1) Å | θ = 2.3–28.0° |
b = 8.699 (1) Å | µ = 0.29 mm−1 |
c = 17.529 (1) Å | T = 296 K |
V = 2179.2 (3) Å3 | Prism, colorless |
Z = 8 | 0.74 × 0.42 × 0.17 mm |
Data collection top
Stoe IPDS-2 diffractometer | 2145 independent reflections |
Radiation source: 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' | 1579 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.054 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.3° |
ω scans | h = −17→17 |
Absorption correction: integration (X-RED32; Stoe, 2002) | k = −10→10 |
Tmin = 0.853, Tmax = 0.960 | l = −21→21 |
14575 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0576P)2 + 0.2248P] where P = (Fo2 + 2Fc2)/3 |
2145 reflections | (Δ/σ)max < 0.001 |
149 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−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 | |
C1 | 0.44292 (17) | 0.3454 (4) | 0.55101 (14) | 0.0881 (8) | |
C2 | 0.40682 (14) | 0.2524 (3) | 0.48790 (11) | 0.0632 (5) | |
C3 | 0.45359 (17) | 0.1588 (4) | 0.43688 (14) | 0.0871 (8) | |
H3 | 0.5183 | 0.1482 | 0.4389 | 0.104* | |
C4 | 0.4020 (2) | 0.0826 (3) | 0.38359 (14) | 0.0814 (7) | |
H4 | 0.4319 | 0.0190 | 0.3486 | 0.098* | |
C5 | 0.30667 (18) | 0.0986 (3) | 0.38109 (12) | 0.0678 (6) | |
H5 | 0.2729 | 0.0457 | 0.3441 | 0.081* | |
C6 | 0.25965 (14) | 0.1915 (2) | 0.43209 (11) | 0.0572 (5) | |
H6 | 0.1950 | 0.2026 | 0.4299 | 0.069* | |
C7 | 0.31182 (13) | 0.2671 (2) | 0.48635 (10) | 0.0487 (4) | |
C8 | 0.28252 (13) | 0.3705 (2) | 0.55056 (10) | 0.0532 (5) | |
H8 | 0.2515 | 0.4620 | 0.5300 | 0.064* | |
C9 | 0.17996 (12) | 0.3814 (2) | 0.65944 (10) | 0.0488 (4) | |
C10 | 0.08888 (16) | 0.4724 (3) | 0.76639 (13) | 0.0753 (7) | |
H10 | 0.0526 | 0.4906 | 0.8095 | 0.090* | |
C11 | 0.12446 (15) | 0.5799 (3) | 0.72203 (13) | 0.0692 (6) | |
H11 | 0.1146 | 0.6838 | 0.7315 | 0.083* | |
N1 | 0.22248 (12) | 0.29647 (17) | 0.60348 (9) | 0.0519 (4) | |
N2 | 0.17718 (12) | 0.53016 (18) | 0.66072 (9) | 0.0577 (4) | |
O1 | 0.52223 (13) | 0.3622 (4) | 0.57194 (13) | 0.1479 (11) | |
O2 | 0.37087 (11) | 0.4144 (2) | 0.58646 (9) | 0.0782 (5) | |
S1 | 0.11938 (4) | 0.29357 (7) | 0.73281 (3) | 0.0703 (2) | |
H1 | 0.2423 (15) | 0.207 (3) | 0.6180 (12) | 0.065 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0593 (14) | 0.137 (2) | 0.0685 (14) | −0.0263 (15) | 0.0052 (11) | −0.0297 (15) |
C2 | 0.0503 (10) | 0.0877 (14) | 0.0516 (10) | −0.0073 (10) | 0.0023 (8) | −0.0099 (10) |
C3 | 0.0563 (13) | 0.136 (2) | 0.0693 (14) | 0.0126 (14) | 0.0060 (11) | −0.0245 (15) |
C4 | 0.0883 (17) | 0.0943 (18) | 0.0618 (13) | 0.0124 (14) | 0.0123 (12) | −0.0202 (12) |
C5 | 0.0844 (16) | 0.0709 (13) | 0.0481 (10) | −0.0091 (12) | −0.0038 (10) | −0.0071 (9) |
C6 | 0.0557 (11) | 0.0610 (11) | 0.0549 (10) | −0.0026 (9) | −0.0063 (9) | 0.0045 (9) |
C7 | 0.0551 (10) | 0.0462 (9) | 0.0447 (9) | −0.0009 (8) | 0.0011 (8) | 0.0042 (7) |
C8 | 0.0612 (11) | 0.0435 (9) | 0.0549 (10) | −0.0018 (9) | 0.0065 (8) | 0.0017 (8) |
C9 | 0.0479 (10) | 0.0518 (10) | 0.0468 (9) | −0.0043 (8) | 0.0006 (8) | 0.0056 (8) |
C10 | 0.0682 (13) | 0.1017 (18) | 0.0559 (12) | 0.0051 (13) | 0.0161 (10) | 0.0001 (12) |
C11 | 0.0729 (14) | 0.0712 (13) | 0.0634 (13) | 0.0089 (11) | 0.0157 (11) | −0.0073 (11) |
N1 | 0.0624 (10) | 0.0400 (8) | 0.0534 (9) | 0.0022 (7) | 0.0065 (7) | 0.0056 (7) |
N2 | 0.0668 (10) | 0.0477 (8) | 0.0587 (9) | 0.0016 (7) | 0.0155 (8) | 0.0004 (7) |
O1 | 0.0632 (12) | 0.274 (3) | 0.1064 (16) | −0.0377 (16) | −0.0035 (11) | −0.0794 (19) |
O2 | 0.0749 (10) | 0.0917 (11) | 0.0679 (9) | −0.0294 (8) | 0.0138 (8) | −0.0302 (8) |
S1 | 0.0723 (4) | 0.0768 (4) | 0.0617 (3) | −0.0114 (3) | 0.0114 (3) | 0.0198 (3) |
Geometric parameters (Å, º) top
C1—O1 | 1.200 (3) | C7—C8 | 1.500 (2) |
C1—O2 | 1.344 (3) | C8—N1 | 1.418 (2) |
C1—C2 | 1.464 (3) | C8—O2 | 1.462 (2) |
C2—C7 | 1.364 (3) | C8—H8 | 0.9800 |
C2—C3 | 1.382 (3) | C9—N2 | 1.295 (2) |
C3—C4 | 1.362 (4) | C9—N1 | 1.370 (2) |
C3—H3 | 0.9300 | C9—S1 | 1.7285 (18) |
C4—C5 | 1.371 (4) | C10—C11 | 1.318 (3) |
C4—H4 | 0.9300 | C10—S1 | 1.720 (3) |
C5—C6 | 1.380 (3) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C11—N2 | 1.382 (2) |
C6—C7 | 1.376 (3) | C11—H11 | 0.9300 |
C6—H6 | 0.9300 | N1—H1 | 0.87 (2) |
| | | |
O1—C1—O2 | 121.8 (2) | N1—C8—O2 | 111.09 (15) |
O1—C1—C2 | 129.1 (3) | N1—C8—C7 | 112.81 (15) |
O2—C1—C2 | 109.04 (19) | O2—C8—C7 | 103.81 (15) |
C7—C2—C3 | 121.6 (2) | N1—C8—H8 | 109.7 |
C7—C2—C1 | 108.30 (19) | O2—C8—H8 | 109.7 |
C3—C2—C1 | 130.1 (2) | C7—C8—H8 | 109.7 |
C4—C3—C2 | 118.0 (2) | N2—C9—N1 | 124.40 (16) |
C4—C3—H3 | 121.0 | N2—C9—S1 | 114.44 (14) |
C2—C3—H3 | 121.0 | N1—C9—S1 | 121.08 (13) |
C3—C4—C5 | 120.7 (2) | C11—C10—S1 | 110.00 (17) |
C3—C4—H4 | 119.7 | C11—C10—H10 | 125.0 |
C5—C4—H4 | 119.7 | S1—C10—H10 | 125.0 |
C4—C5—C6 | 121.5 (2) | C10—C11—N2 | 116.5 (2) |
C4—C5—H5 | 119.2 | C10—C11—H11 | 121.7 |
C6—C5—H5 | 119.2 | N2—C11—H11 | 121.7 |
C7—C6—C5 | 117.65 (19) | C9—N1—C8 | 119.45 (15) |
C7—C6—H6 | 121.2 | C9—N1—H1 | 114.8 (14) |
C5—C6—H6 | 121.2 | C8—N1—H1 | 113.7 (15) |
C2—C7—C6 | 120.54 (18) | C9—N2—C11 | 110.07 (17) |
C2—C7—C8 | 108.61 (16) | C1—O2—C8 | 110.22 (15) |
C6—C7—C8 | 130.85 (18) | C10—S1—C9 | 88.94 (10) |
| | | |
O1—C1—C2—C7 | 179.2 (4) | C2—C7—C8—O2 | 1.4 (2) |
O2—C1—C2—C7 | −0.1 (3) | C6—C7—C8—O2 | −179.43 (19) |
O1—C1—C2—C3 | 1.0 (6) | S1—C10—C11—N2 | −0.4 (3) |
O2—C1—C2—C3 | −178.3 (3) | N2—C9—N1—C8 | 12.4 (3) |
C7—C2—C3—C4 | 1.0 (4) | S1—C9—N1—C8 | −171.02 (14) |
C1—C2—C3—C4 | 179.1 (3) | O2—C8—N1—C9 | 72.6 (2) |
C2—C3—C4—C5 | −0.1 (4) | C7—C8—N1—C9 | −171.33 (16) |
C3—C4—C5—C6 | −0.2 (4) | N1—C9—N2—C11 | 176.40 (18) |
C4—C5—C6—C7 | −0.5 (3) | S1—C9—N2—C11 | −0.4 (2) |
C3—C2—C7—C6 | −1.7 (3) | C10—C11—N2—C9 | 0.5 (3) |
C1—C2—C7—C6 | 179.9 (2) | O1—C1—O2—C8 | −178.4 (3) |
C3—C2—C7—C8 | 177.6 (2) | C2—C1—O2—C8 | 1.0 (3) |
C1—C2—C7—C8 | −0.9 (3) | N1—C8—O2—C1 | 120.1 (2) |
C5—C6—C7—C2 | 1.4 (3) | C7—C8—O2—C1 | −1.4 (2) |
C5—C6—C7—C8 | −177.68 (19) | C11—C10—S1—C9 | 0.19 (19) |
C2—C7—C8—N1 | −118.95 (19) | N2—C9—S1—C10 | 0.10 (17) |
C6—C7—C8—N1 | 60.2 (3) | N1—C9—S1—C10 | −176.77 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2i | 0.87 (2) | 2.06 (2) | 2.903 (2) | 164 (2) |
C6—H6···O1ii | 0.93 | 2.53 | 3.426 (3) | 161 |
C10—H10···O1iii | 0.93 | 2.40 | 3.140 (3) | 137 |
C4—H4···Cg1iv | 0.93 | 3.12 | 3.749 (3) | 127 |
C5—H5···Cg1v | 0.93 | 3.06 | 3.896 (2) | 150 |
C8—H8···Cg2vi | 0.98 | 2.93 | 3.888 (2) | 164 |
Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) x−1/2, −y+1/2, −z+1; (iii) x−1/2, y, −z+3/2; (iv) x+1/2, −y+1/2, −z+1; (v) x, −y−1/2, z−3/2; (vi) −x−1/2, y−1/2, z. |