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In the title compound, C14H10ClNO3S, the mean planes of benzisothia­zole moiety and the 4-chlorobenzene ring make a dihedral angle of 66.2 (5)°. Weak inter­molecular C—H...O hydrogen bonds link mol­ecules into linear chains extending along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001140/cv2002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001140/cv2002Isup2.hkl
Contains datablock I

CCDC reference: 298401

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.050
  • wR factor = 0.152
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for C10 - C11 .. 6.25 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C11 - C12 .. 5.27 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10 PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C9 -C14 1.34 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT411_ALERT_2_C Short Inter H...H Contact H8B .. H11A .. 2.13 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O1 .. 3.23 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1999); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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.

2-(4-Chlorobenzyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide top
Crystal data top
C14H10ClNO3SZ = 2
Mr = 307.74F(000) = 316
Triclinic, P1Dx = 1.599 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2657 (15) ÅCell parameters from 5601 reflections
b = 7.4743 (15) Åθ = 1.6–27.5°
c = 13.317 (3) ŵ = 0.47 mm1
α = 97.50 (3)°T = 293 K
β = 102.82 (3)°Plate, colourless
γ = 111.25 (3)°0.53 × 0.47 × 0.11 mm
V = 639.3 (3) Å3
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
2201 independent reflections
Radiation source: Rotating Anode2065 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 99
Tmin = 0.753, Tmax = 0.953k = 88
2851 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0884P)2 + 0.4878P]
where P = (Fo2 + 2Fc2)/3
2201 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.55 e Å3
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
xyzUiso*/Ueq
Cl11.10855 (13)0.79585 (16)0.58256 (7)0.0666 (3)
S10.25031 (10)0.87871 (10)0.19147 (5)0.0401 (3)
O10.4305 (3)1.0408 (3)0.25773 (17)0.0554 (6)
O20.0578 (3)0.8686 (3)0.20338 (18)0.0541 (6)
O30.2781 (4)0.3960 (3)0.10868 (18)0.0555 (6)
N10.2725 (4)0.6683 (4)0.20488 (19)0.0433 (6)
C10.2467 (4)0.8388 (4)0.0586 (2)0.0367 (6)
C20.2309 (4)0.9585 (4)0.0094 (2)0.0435 (6)
H2B0.22411.07870.01250.052*
C30.2258 (4)0.8923 (5)0.1120 (2)0.0474 (7)
H3A0.21320.96870.16080.057*
C40.2388 (5)0.7153 (5)0.1438 (2)0.0478 (7)
H4A0.23650.67500.21330.057*
C50.2552 (4)0.5970 (4)0.0737 (2)0.0435 (6)
H5A0.26430.47770.09500.052*
C60.2578 (4)0.6604 (4)0.0285 (2)0.0368 (6)
C70.2700 (4)0.5548 (4)0.1141 (2)0.0409 (6)
C80.2727 (5)0.6030 (5)0.3038 (2)0.0511 (7)
H8A0.20050.46050.28730.061*
H8B0.19750.65890.34040.061*
C90.4850 (5)0.6610 (4)0.3760 (2)0.0433 (6)
C100.6353 (6)0.6226 (7)0.3420 (3)0.0698 (11)
H10A0.60280.56360.27080.084*
C110.8223 (5)0.6631 (6)0.4029 (2)0.0543 (8)
H11A0.91880.63450.37620.065*
C120.8643 (5)0.7447 (5)0.5016 (2)0.0463 (7)
C130.7316 (5)0.7926 (5)0.5457 (2)0.0515 (7)
H13A0.77010.85170.61730.062*
C140.5394 (5)0.7505 (5)0.4808 (2)0.0502 (7)
H14A0.44520.78280.50810.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0534 (5)0.0964 (7)0.0614 (6)0.0387 (5)0.0157 (4)0.0323 (5)
S10.0409 (4)0.0393 (4)0.0388 (4)0.0184 (3)0.0103 (3)0.0005 (3)
O10.0537 (13)0.0484 (12)0.0468 (12)0.0121 (10)0.0077 (10)0.0082 (9)
O20.0519 (12)0.0623 (13)0.0581 (13)0.0324 (11)0.0229 (10)0.0071 (11)
O30.0703 (15)0.0410 (11)0.0591 (14)0.0297 (11)0.0155 (11)0.0089 (10)
N10.0513 (14)0.0449 (13)0.0382 (12)0.0254 (11)0.0118 (10)0.0086 (10)
C10.0321 (13)0.0368 (13)0.0378 (13)0.0144 (11)0.0073 (10)0.0016 (11)
C20.0379 (14)0.0391 (14)0.0535 (17)0.0179 (12)0.0104 (12)0.0092 (12)
C30.0417 (15)0.0553 (17)0.0488 (17)0.0217 (13)0.0132 (13)0.0175 (13)
C40.0440 (16)0.0580 (18)0.0399 (15)0.0200 (14)0.0134 (12)0.0063 (13)
C50.0405 (15)0.0418 (15)0.0451 (15)0.0172 (12)0.0117 (12)0.0002 (12)
C60.0317 (13)0.0361 (13)0.0406 (14)0.0147 (10)0.0084 (11)0.0035 (11)
C70.0376 (14)0.0400 (15)0.0440 (15)0.0172 (11)0.0099 (12)0.0050 (11)
C80.0514 (17)0.0600 (18)0.0450 (16)0.0225 (15)0.0174 (14)0.0167 (14)
C90.0491 (16)0.0488 (16)0.0419 (15)0.0256 (13)0.0189 (13)0.0170 (12)
C100.082 (3)0.113 (3)0.0366 (16)0.065 (2)0.0195 (17)0.0082 (18)
C110.0544 (17)0.100 (3)0.0359 (15)0.0564 (19)0.0207 (13)0.0171 (15)
C120.0494 (16)0.0550 (17)0.0471 (16)0.0279 (14)0.0193 (13)0.0244 (13)
C130.0573 (18)0.0597 (19)0.0393 (15)0.0278 (15)0.0147 (14)0.0041 (13)
C140.0516 (17)0.0615 (18)0.0475 (16)0.0296 (15)0.0236 (14)0.0094 (14)
Geometric parameters (Å, º) top
Cl1—C121.735 (3)C5—H5A0.9300
S1—O21.418 (2)C6—C71.474 (4)
S1—O11.421 (2)C7—O31.203 (3)
S1—N11.666 (2)C8—C91.497 (4)
S1—C11.748 (3)C8—H8A0.9700
O3—C71.203 (3)C8—H8B0.9700
N1—C71.376 (4)C9—C141.369 (4)
N1—C81.463 (4)C9—C101.376 (4)
C1—C21.369 (4)C10—C111.321 (5)
C1—C61.378 (4)C10—H10A0.9300
C2—C31.378 (4)C11—C121.293 (4)
C2—H2B0.9300C11—H11A0.9300
C3—C41.379 (4)C12—C131.360 (4)
C3—H3A0.9300C13—C141.368 (5)
C4—C51.383 (4)C13—H13A0.9300
C4—H4A0.9300C14—H14A0.9300
C5—C61.375 (4)
O2—S1—O1117.21 (14)O3—C7—N1123.9 (3)
O2—S1—N1109.46 (14)O3—C7—C6127.1 (3)
O1—S1—N1109.51 (14)O3—C7—C6127.1 (3)
O2—S1—C1112.09 (13)N1—C7—C6108.9 (2)
O1—S1—C1113.01 (14)N1—C8—C9113.3 (2)
N1—S1—C192.78 (12)N1—C8—H8A108.9
C7—N1—C8123.4 (2)C9—C8—H8A108.9
C7—N1—S1115.0 (2)N1—C8—H8B108.9
C8—N1—S1121.3 (2)C9—C8—H8B108.9
C2—C1—C6122.9 (3)H8A—C8—H8B107.7
C2—C1—S1127.5 (2)C14—C9—C10115.9 (3)
C6—C1—S1109.6 (2)C14—C9—C8121.8 (3)
C1—C2—C3116.8 (3)C10—C9—C8122.2 (3)
C1—C2—H2B121.6C11—C10—C9124.9 (3)
C3—C2—H2B121.6C11—C10—H10A117.6
C2—C3—C4121.5 (3)C9—C10—H10A117.6
C2—C3—H3A119.3C12—C11—C10116.6 (3)
C4—C3—H3A119.3C12—C11—H11A121.7
C3—C4—C5120.8 (3)C10—C11—H11A121.7
C3—C4—H4A119.6C11—C12—C13124.8 (3)
C5—C4—H4A119.6C11—C12—Cl1116.9 (2)
C6—C5—C4118.2 (3)C13—C12—Cl1118.3 (2)
C6—C5—H5A120.9C12—C13—C14117.5 (3)
C4—C5—H5A120.9C12—C13—H13A121.2
C5—C6—C1119.8 (3)C14—C13—H13A121.2
C5—C6—C7126.6 (2)C13—C14—C9120.3 (3)
C1—C6—C7113.6 (2)C13—C14—H14A119.9
O3—C7—N1123.9 (3)C9—C14—H14A119.9
O2—S1—N1—C7112.1 (2)C8—N1—C7—O33.8 (4)
O1—S1—N1—C7118.1 (2)S1—N1—C7—O3177.7 (2)
C1—S1—N1—C72.5 (2)C8—N1—C7—C6176.6 (2)
O2—S1—N1—C861.9 (3)S1—N1—C7—C62.8 (3)
O1—S1—N1—C867.9 (3)C5—C6—C7—O30.6 (5)
C1—S1—N1—C8176.5 (2)C1—C6—C7—O3178.9 (3)
O2—S1—C1—C267.8 (3)C5—C6—C7—O30.6 (5)
O1—S1—C1—C267.3 (3)C1—C6—C7—O3178.9 (3)
N1—S1—C1—C2179.9 (3)C5—C6—C7—N1178.9 (3)
O2—S1—C1—C6110.9 (2)C1—C6—C7—N11.6 (3)
O1—S1—C1—C6114.0 (2)C7—N1—C8—C991.5 (3)
N1—S1—C1—C61.5 (2)S1—N1—C8—C995.1 (3)
C6—C1—C2—C30.2 (4)N1—C8—C9—C14131.0 (3)
S1—C1—C2—C3178.3 (2)N1—C8—C9—C1051.0 (4)
C1—C2—C3—C40.9 (4)C14—C9—C10—C110.9 (6)
C2—C3—C4—C50.7 (5)C8—C9—C10—C11177.2 (4)
C3—C4—C5—C60.1 (4)C9—C10—C11—C120.1 (7)
C4—C5—C6—C10.8 (4)C10—C11—C12—C130.8 (6)
C4—C5—C6—C7178.7 (3)C10—C11—C12—Cl1179.3 (3)
C2—C1—C6—C50.6 (4)C11—C12—C13—C140.3 (5)
S1—C1—C6—C5179.4 (2)Cl1—C12—C13—C14179.8 (2)
C2—C1—C6—C7178.9 (2)C12—C13—C14—C90.9 (5)
S1—C1—C6—C70.2 (3)C10—C9—C14—C131.4 (5)
C8—N1—C7—O33.8 (4)C8—C9—C14—C13176.7 (3)
S1—N1—C7—O3177.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···O3i0.932.393.300 (4)165
Symmetry code: (i) x, y+1, z.
 

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