In the title molecule, C
14H
11NO
3S, the benzoisothiazole ring system and the benzyl group form a dihedral angle of 87.7 (9)°. The crystal structure is stabilized by weak intermolecular C—H
O hydrogen bonds.
Supporting information
CCDC reference: 627973
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.100
- Data-to-parameter ratio = 17.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
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
0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.
Crystal data top
C14H11NO3S | F(000) = 568 |
Mr = 273.30 | Dx = 1.491 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2yn | Cell parameters from 4168 reflections |
a = 6.6073 (18) Å | θ = 2.3–28.7° |
b = 10.223 (3) Å | µ = 0.27 mm−1 |
c = 18.221 (5) Å | T = 113 K |
β = 98.459 (4)° | Block, colorless |
V = 1217.3 (6) Å3 | 0.32 × 0.28 × 0.24 mm |
Z = 4 | |
Data collection top
Rigaku Saturn diffractometer | 3095 independent reflections |
Radiation source: rotating anode | 2407 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.035 |
Detector resolution: 7.31 pixels mm-1 | θmax = 28.7°, θmin = 2.3° |
ω scans | h = −7→8 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −12→13 |
Tmin = 0.919, Tmax = 0.938 | l = −24→24 |
11532 measured reflections | |
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)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0593P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
3095 reflections | Δρmax = 0.37 e Å−3 |
174 parameters | Δρmin = −0.45 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: 0.037 (4) |
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 | |
S1 | 0.27468 (5) | 0.39036 (3) | 0.057657 (18) | 0.01345 (12) | |
O1 | 0.78969 (14) | 0.37272 (10) | 0.17415 (6) | 0.0218 (2) | |
O2 | 0.12807 (13) | 0.28842 (9) | 0.06234 (6) | 0.0186 (2) | |
O3 | 0.26725 (14) | 0.45438 (10) | −0.01269 (5) | 0.0193 (2) | |
N1 | 0.50961 (16) | 0.33409 (11) | 0.08645 (6) | 0.0143 (2) | |
C1 | 0.6151 (2) | 0.39697 (13) | 0.14796 (8) | 0.0147 (3) | |
C2 | 0.47716 (19) | 0.49523 (12) | 0.17553 (7) | 0.0145 (3) | |
C3 | 0.28609 (19) | 0.50127 (13) | 0.13159 (7) | 0.0142 (3) | |
C4 | 0.1324 (2) | 0.58406 (13) | 0.14819 (8) | 0.0175 (3) | |
H4 | 0.0023 | 0.5873 | 0.1181 | 0.021* | |
C5 | 0.1777 (2) | 0.66163 (14) | 0.21070 (9) | 0.0203 (3) | |
H5 | 0.0758 | 0.7191 | 0.2238 | 0.024* | |
C6 | 0.3692 (2) | 0.65783 (14) | 0.25519 (8) | 0.0192 (3) | |
H6 | 0.3958 | 0.7128 | 0.2976 | 0.023* | |
C7 | 0.5210 (2) | 0.57381 (14) | 0.23761 (8) | 0.0177 (3) | |
H7 | 0.6513 | 0.5706 | 0.2675 | 0.021* | |
C8 | 0.61192 (19) | 0.24306 (13) | 0.04181 (8) | 0.0158 (3) | |
H8A | 0.7479 | 0.2789 | 0.0360 | 0.019* | |
H8B | 0.5307 | 0.2362 | −0.0082 | 0.019* | |
C9 | 0.6394 (2) | 0.10802 (12) | 0.07527 (7) | 0.0147 (3) | |
C10 | 0.4931 (2) | 0.05155 (14) | 0.11285 (8) | 0.0190 (3) | |
H10 | 0.3730 | 0.0992 | 0.1187 | 0.023* | |
C11 | 0.5206 (2) | −0.07371 (15) | 0.14194 (9) | 0.0226 (3) | |
H11 | 0.4208 | −0.1107 | 0.1683 | 0.027* | |
C12 | 0.6938 (2) | −0.14523 (14) | 0.13261 (9) | 0.0227 (3) | |
H12 | 0.7122 | −0.2312 | 0.1523 | 0.027* | |
C13 | 0.8393 (2) | −0.09053 (14) | 0.09447 (9) | 0.0220 (3) | |
H13 | 0.9568 | −0.1396 | 0.0872 | 0.026* | |
C14 | 0.8139 (2) | 0.03614 (14) | 0.06678 (8) | 0.0182 (3) | |
H14 | 0.9161 | 0.0740 | 0.0419 | 0.022* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.01135 (18) | 0.01441 (18) | 0.01385 (18) | −0.00060 (12) | −0.00057 (12) | 0.00056 (13) |
O1 | 0.0149 (5) | 0.0294 (6) | 0.0195 (5) | 0.0038 (4) | −0.0028 (4) | −0.0002 (4) |
O2 | 0.0145 (5) | 0.0165 (5) | 0.0247 (6) | −0.0044 (4) | 0.0025 (4) | −0.0015 (4) |
O3 | 0.0183 (5) | 0.0241 (5) | 0.0144 (5) | −0.0009 (4) | −0.0013 (4) | 0.0047 (4) |
N1 | 0.0125 (5) | 0.0152 (6) | 0.0148 (6) | 0.0014 (4) | 0.0009 (4) | 0.0002 (5) |
C1 | 0.0143 (6) | 0.0160 (6) | 0.0139 (6) | −0.0017 (5) | 0.0021 (5) | 0.0024 (5) |
C2 | 0.0144 (6) | 0.0136 (6) | 0.0152 (7) | −0.0011 (5) | 0.0013 (5) | 0.0024 (5) |
C3 | 0.0149 (6) | 0.0129 (6) | 0.0145 (6) | −0.0006 (5) | 0.0007 (5) | 0.0007 (5) |
C4 | 0.0146 (6) | 0.0170 (7) | 0.0201 (7) | −0.0002 (5) | −0.0006 (5) | 0.0002 (6) |
C5 | 0.0208 (7) | 0.0170 (7) | 0.0237 (8) | 0.0020 (6) | 0.0049 (6) | −0.0018 (6) |
C6 | 0.0239 (7) | 0.0173 (7) | 0.0165 (7) | −0.0022 (6) | 0.0032 (5) | −0.0019 (6) |
C7 | 0.0174 (7) | 0.0199 (7) | 0.0147 (7) | −0.0031 (5) | −0.0012 (5) | 0.0011 (6) |
C8 | 0.0152 (6) | 0.0181 (7) | 0.0146 (7) | 0.0010 (5) | 0.0039 (5) | 0.0010 (5) |
C9 | 0.0168 (6) | 0.0141 (6) | 0.0126 (6) | −0.0012 (5) | −0.0003 (5) | −0.0021 (5) |
C10 | 0.0177 (7) | 0.0202 (7) | 0.0191 (7) | −0.0009 (5) | 0.0028 (5) | −0.0002 (6) |
C11 | 0.0236 (7) | 0.0202 (7) | 0.0237 (8) | −0.0068 (6) | 0.0026 (6) | 0.0027 (6) |
C12 | 0.0307 (8) | 0.0140 (7) | 0.0221 (8) | −0.0014 (6) | −0.0008 (6) | 0.0009 (6) |
C13 | 0.0249 (7) | 0.0174 (7) | 0.0235 (8) | 0.0045 (6) | 0.0026 (6) | −0.0020 (6) |
C14 | 0.0197 (7) | 0.0185 (7) | 0.0166 (7) | 0.0002 (5) | 0.0031 (5) | −0.0009 (5) |
Geometric parameters (Å, º) top
S1—O3 | 1.4336 (10) | C6—H6 | 0.9500 |
S1—O2 | 1.4339 (10) | C7—H7 | 0.9500 |
S1—N1 | 1.6661 (12) | C8—C9 | 1.5092 (18) |
S1—C3 | 1.7538 (14) | C8—H8A | 0.9900 |
O1—C1 | 1.2076 (16) | C8—H8B | 0.9900 |
N1—C1 | 1.3875 (18) | C9—C10 | 1.3899 (19) |
N1—C8 | 1.4651 (17) | C9—C14 | 1.3945 (19) |
C1—C2 | 1.4921 (19) | C10—C11 | 1.388 (2) |
C2—C7 | 1.3828 (19) | C10—H10 | 0.9500 |
C2—C3 | 1.3933 (18) | C11—C12 | 1.389 (2) |
C3—C4 | 1.3891 (19) | C11—H11 | 0.9500 |
C4—C5 | 1.384 (2) | C12—C13 | 1.385 (2) |
C4—H4 | 0.9500 | C12—H12 | 0.9500 |
C5—C6 | 1.399 (2) | C13—C14 | 1.391 (2) |
C5—H5 | 0.9500 | C13—H13 | 0.9500 |
C6—C7 | 1.393 (2) | C14—H14 | 0.9500 |
| | | |
O3—S1—O2 | 116.77 (6) | C2—C7—C6 | 118.38 (13) |
O3—S1—N1 | 110.30 (6) | C2—C7—H7 | 120.8 |
O2—S1—N1 | 109.67 (6) | C6—C7—H7 | 120.8 |
O3—S1—C3 | 112.56 (7) | N1—C8—C9 | 113.25 (11) |
O2—S1—C3 | 112.16 (6) | N1—C8—H8A | 108.9 |
N1—S1—C3 | 92.78 (6) | C9—C8—H8A | 108.9 |
C1—N1—C8 | 121.65 (11) | N1—C8—H8B | 108.9 |
C1—N1—S1 | 115.36 (9) | C9—C8—H8B | 108.9 |
C8—N1—S1 | 121.94 (9) | H8A—C8—H8B | 107.7 |
O1—C1—N1 | 124.14 (13) | C10—C9—C14 | 118.82 (13) |
O1—C1—C2 | 126.90 (13) | C10—C9—C8 | 121.86 (12) |
N1—C1—C2 | 108.95 (11) | C14—C9—C8 | 119.30 (12) |
C7—C2—C3 | 120.48 (12) | C11—C10—C9 | 120.65 (13) |
C7—C2—C1 | 127.00 (12) | C11—C10—H10 | 119.7 |
C3—C2—C1 | 112.52 (12) | C9—C10—H10 | 119.7 |
C4—C3—C2 | 122.11 (13) | C10—C11—C12 | 120.21 (14) |
C4—C3—S1 | 127.66 (10) | C10—C11—H11 | 119.9 |
C2—C3—S1 | 110.22 (10) | C12—C11—H11 | 119.9 |
C5—C4—C3 | 116.86 (12) | C13—C12—C11 | 119.62 (14) |
C5—C4—H4 | 121.6 | C13—C12—H12 | 120.2 |
C3—C4—H4 | 121.6 | C11—C12—H12 | 120.2 |
C4—C5—C6 | 121.91 (13) | C12—C13—C14 | 120.14 (13) |
C4—C5—H5 | 119.0 | C12—C13—H13 | 119.9 |
C6—C5—H5 | 119.0 | C14—C13—H13 | 119.9 |
C7—C6—C5 | 120.26 (14) | C13—C14—C9 | 120.54 (13) |
C7—C6—H6 | 119.9 | C13—C14—H14 | 119.7 |
C5—C6—H6 | 119.9 | C9—C14—H14 | 119.7 |
| | | |
O3—S1—N1—C1 | 111.40 (11) | O2—S1—C3—C2 | 114.92 (10) |
O2—S1—N1—C1 | −118.65 (10) | N1—S1—C3—C2 | 2.36 (11) |
C3—S1—N1—C1 | −3.91 (11) | C2—C3—C4—C5 | 0.3 (2) |
O3—S1—N1—C8 | −57.12 (12) | S1—C3—C4—C5 | 178.99 (11) |
O2—S1—N1—C8 | 72.84 (11) | C3—C4—C5—C6 | 0.3 (2) |
C3—S1—N1—C8 | −172.42 (11) | C4—C5—C6—C7 | −0.4 (2) |
C8—N1—C1—O1 | −8.1 (2) | C3—C2—C7—C6 | 0.5 (2) |
S1—N1—C1—O1 | −176.61 (11) | C1—C2—C7—C6 | −178.54 (13) |
C8—N1—C1—C2 | 172.73 (11) | C5—C6—C7—C2 | 0.0 (2) |
S1—N1—C1—C2 | 4.18 (14) | C1—N1—C8—C9 | 80.73 (15) |
O1—C1—C2—C7 | −2.3 (2) | S1—N1—C8—C9 | −111.47 (11) |
N1—C1—C2—C7 | 176.84 (13) | N1—C8—C9—C10 | 36.26 (18) |
O1—C1—C2—C3 | 178.56 (13) | N1—C8—C9—C14 | −145.40 (12) |
N1—C1—C2—C3 | −2.26 (16) | C14—C9—C10—C11 | 0.5 (2) |
C7—C2—C3—C4 | −0.7 (2) | C8—C9—C10—C11 | 178.85 (13) |
C1—C2—C3—C4 | 178.47 (12) | C9—C10—C11—C12 | −1.2 (2) |
C7—C2—C3—S1 | −179.58 (10) | C10—C11—C12—C13 | 0.4 (2) |
C1—C2—C3—S1 | −0.42 (15) | C11—C12—C13—C14 | 1.1 (2) |
O3—S1—C3—C4 | 70.20 (14) | C12—C13—C14—C9 | −1.8 (2) |
O2—S1—C3—C4 | −63.89 (14) | C10—C9—C14—C13 | 1.0 (2) |
N1—S1—C3—C4 | −176.45 (13) | C8—C9—C14—C13 | −177.43 (13) |
O3—S1—C3—C2 | −110.99 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O2i | 0.99 | 2.49 | 3.4074 (18) | 154 |
C4—H4···O3ii | 0.95 | 2.46 | 3.3623 (19) | 159 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y+1, −z. |