2-(4-Chloro­benz­yl)-1,2-benzisothia­zol-3(2H)-one 1,1-dioxide

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.

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

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Computing details

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

Crystal data

C14H10ClNO3S	Z = 2
Mr = 307.74	F(000) = 316
Triclinic, P1	Dx = 1.599 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2657 (15) Å	Cell parameters from 5601 reflections
b = 7.4743 (15) Å	θ = 1.6–27.5°
c = 13.317 (3) Å	µ = 0.47 mm^−1
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) Å^3

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer	2201 independent reflections
Radiation source: Rotating Anode	2065 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.753, Tmax = 0.953	k = −8→8
2851 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0884P)^2 + 0.4878P] where P = (Fo^2 + 2Fc^2)/3
2201 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.55 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	1.10855 (13)	0.79585 (16)	0.58256 (7)	0.0666 (3)
S1	0.25031 (10)	0.87871 (10)	0.19147 (5)	0.0401 (3)
O1	0.4305 (3)	1.0408 (3)	0.25773 (17)	0.0554 (6)
O2	0.0578 (3)	0.8686 (3)	0.20338 (18)	0.0541 (6)
O3	0.2781 (4)	0.3960 (3)	0.10868 (18)	0.0555 (6)
N1	0.2725 (4)	0.6683 (4)	0.20488 (19)	0.0433 (6)
C1	0.2467 (4)	0.8388 (4)	0.0586 (2)	0.0367 (6)
C2	0.2309 (4)	0.9585 (4)	−0.0094 (2)	0.0435 (6)
H2B	0.2241	1.0787	0.0125	0.052*
C3	0.2258 (4)	0.8923 (5)	−0.1120 (2)	0.0474 (7)
H3A	0.2132	0.9687	−0.1608	0.057*
C4	0.2388 (5)	0.7153 (5)	−0.1438 (2)	0.0478 (7)
H4A	0.2365	0.6750	−0.2133	0.057*
C5	0.2552 (4)	0.5970 (4)	−0.0737 (2)	0.0435 (6)
H5A	0.2643	0.4777	−0.0950	0.052*
C6	0.2578 (4)	0.6604 (4)	0.0285 (2)	0.0368 (6)
C7	0.2700 (4)	0.5548 (4)	0.1141 (2)	0.0409 (6)
C8	0.2727 (5)	0.6030 (5)	0.3038 (2)	0.0511 (7)
H8A	0.2005	0.4605	0.2873	0.061*
H8B	0.1975	0.6589	0.3404	0.061*
C9	0.4850 (5)	0.6610 (4)	0.3760 (2)	0.0433 (6)
C10	0.6353 (6)	0.6226 (7)	0.3420 (3)	0.0698 (11)
H10A	0.6028	0.5636	0.2708	0.084*
C11	0.8223 (5)	0.6631 (6)	0.4029 (2)	0.0543 (8)
H11A	0.9188	0.6345	0.3762	0.065*
C12	0.8643 (5)	0.7447 (5)	0.5016 (2)	0.0463 (7)
C13	0.7316 (5)	0.7926 (5)	0.5457 (2)	0.0515 (7)
H13A	0.7701	0.8517	0.6173	0.062*
C14	0.5394 (5)	0.7505 (5)	0.4808 (2)	0.0502 (7)
H14A	0.4452	0.7828	0.5081	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0534 (5)	0.0964 (7)	0.0614 (6)	0.0387 (5)	0.0157 (4)	0.0323 (5)
S1	0.0409 (4)	0.0393 (4)	0.0388 (4)	0.0184 (3)	0.0103 (3)	0.0005 (3)
O1	0.0537 (13)	0.0484 (12)	0.0468 (12)	0.0121 (10)	0.0077 (10)	−0.0082 (9)
O2	0.0519 (12)	0.0623 (13)	0.0581 (13)	0.0324 (11)	0.0229 (10)	0.0071 (11)
O3	0.0703 (15)	0.0410 (11)	0.0591 (14)	0.0297 (11)	0.0155 (11)	0.0089 (10)
N1	0.0513 (14)	0.0449 (13)	0.0382 (12)	0.0254 (11)	0.0118 (10)	0.0086 (10)
C1	0.0321 (13)	0.0368 (13)	0.0378 (13)	0.0144 (11)	0.0073 (10)	0.0016 (11)
C2	0.0379 (14)	0.0391 (14)	0.0535 (17)	0.0179 (12)	0.0104 (12)	0.0092 (12)
C3	0.0417 (15)	0.0553 (17)	0.0488 (17)	0.0217 (13)	0.0132 (13)	0.0175 (13)
C4	0.0440 (16)	0.0580 (18)	0.0399 (15)	0.0200 (14)	0.0134 (12)	0.0063 (13)
C5	0.0405 (15)	0.0418 (15)	0.0451 (15)	0.0172 (12)	0.0117 (12)	−0.0002 (12)
C6	0.0317 (13)	0.0361 (13)	0.0406 (14)	0.0147 (10)	0.0084 (11)	0.0035 (11)
C7	0.0376 (14)	0.0400 (15)	0.0440 (15)	0.0172 (11)	0.0099 (12)	0.0050 (11)
C8	0.0514 (17)	0.0600 (18)	0.0450 (16)	0.0225 (15)	0.0174 (14)	0.0167 (14)
C9	0.0491 (16)	0.0488 (16)	0.0419 (15)	0.0256 (13)	0.0189 (13)	0.0170 (12)
C10	0.082 (3)	0.113 (3)	0.0366 (16)	0.065 (2)	0.0195 (17)	0.0082 (18)
C11	0.0544 (17)	0.100 (3)	0.0359 (15)	0.0564 (19)	0.0207 (13)	0.0171 (15)
C12	0.0494 (16)	0.0550 (17)	0.0471 (16)	0.0279 (14)	0.0193 (13)	0.0244 (13)
C13	0.0573 (18)	0.0597 (19)	0.0393 (15)	0.0278 (15)	0.0147 (14)	0.0041 (13)
C14	0.0516 (17)	0.0615 (18)	0.0475 (16)	0.0296 (15)	0.0236 (14)	0.0094 (14)

Geometric parameters (Å, º)

Cl1—C12	1.735 (3)	C5—H5A	0.9300
S1—O2	1.418 (2)	C6—C7	1.474 (4)
S1—O1	1.421 (2)	C7—O3	1.203 (3)
S1—N1	1.666 (2)	C8—C9	1.497 (4)
S1—C1	1.748 (3)	C8—H8A	0.9700
O3—C7	1.203 (3)	C8—H8B	0.9700
N1—C7	1.376 (4)	C9—C14	1.369 (4)
N1—C8	1.463 (4)	C9—C10	1.376 (4)
C1—C2	1.369 (4)	C10—C11	1.321 (5)
C1—C6	1.378 (4)	C10—H10A	0.9300
C2—C3	1.378 (4)	C11—C12	1.293 (4)
C2—H2B	0.9300	C11—H11A	0.9300
C3—C4	1.379 (4)	C12—C13	1.360 (4)
C3—H3A	0.9300	C13—C14	1.368 (5)
C4—C5	1.383 (4)	C13—H13A	0.9300
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.375 (4)
O2—S1—O1	117.21 (14)	O3—C7—N1	123.9 (3)
O2—S1—N1	109.46 (14)	O3—C7—C6	127.1 (3)
O1—S1—N1	109.51 (14)	O3—C7—C6	127.1 (3)
O2—S1—C1	112.09 (13)	N1—C7—C6	108.9 (2)
O1—S1—C1	113.01 (14)	N1—C8—C9	113.3 (2)
N1—S1—C1	92.78 (12)	N1—C8—H8A	108.9
C7—N1—C8	123.4 (2)	C9—C8—H8A	108.9
C7—N1—S1	115.0 (2)	N1—C8—H8B	108.9
C8—N1—S1	121.3 (2)	C9—C8—H8B	108.9
C2—C1—C6	122.9 (3)	H8A—C8—H8B	107.7
C2—C1—S1	127.5 (2)	C14—C9—C10	115.9 (3)
C6—C1—S1	109.6 (2)	C14—C9—C8	121.8 (3)
C1—C2—C3	116.8 (3)	C10—C9—C8	122.2 (3)
C1—C2—H2B	121.6	C11—C10—C9	124.9 (3)
C3—C2—H2B	121.6	C11—C10—H10A	117.6
C2—C3—C4	121.5 (3)	C9—C10—H10A	117.6
C2—C3—H3A	119.3	C12—C11—C10	116.6 (3)
C4—C3—H3A	119.3	C12—C11—H11A	121.7
C3—C4—C5	120.8 (3)	C10—C11—H11A	121.7
C3—C4—H4A	119.6	C11—C12—C13	124.8 (3)
C5—C4—H4A	119.6	C11—C12—Cl1	116.9 (2)
C6—C5—C4	118.2 (3)	C13—C12—Cl1	118.3 (2)
C6—C5—H5A	120.9	C12—C13—C14	117.5 (3)
C4—C5—H5A	120.9	C12—C13—H13A	121.2
C5—C6—C1	119.8 (3)	C14—C13—H13A	121.2
C5—C6—C7	126.6 (2)	C13—C14—C9	120.3 (3)
C1—C6—C7	113.6 (2)	C13—C14—H14A	119.9
O3—C7—N1	123.9 (3)	C9—C14—H14A	119.9
O2—S1—N1—C7	112.1 (2)	C8—N1—C7—O3	−3.8 (4)
O1—S1—N1—C7	−118.1 (2)	S1—N1—C7—O3	−177.7 (2)
C1—S1—N1—C7	−2.5 (2)	C8—N1—C7—C6	176.6 (2)
O2—S1—N1—C8	−61.9 (3)	S1—N1—C7—C6	2.8 (3)
O1—S1—N1—C8	67.9 (3)	C5—C6—C7—O3	−0.6 (5)
C1—S1—N1—C8	−176.5 (2)	C1—C6—C7—O3	178.9 (3)
O2—S1—C1—C2	67.8 (3)	C5—C6—C7—O3	−0.6 (5)
O1—S1—C1—C2	−67.3 (3)	C1—C6—C7—O3	178.9 (3)
N1—S1—C1—C2	−179.9 (3)	C5—C6—C7—N1	178.9 (3)
O2—S1—C1—C6	−110.9 (2)	C1—C6—C7—N1	−1.6 (3)
O1—S1—C1—C6	114.0 (2)	C7—N1—C8—C9	91.5 (3)
N1—S1—C1—C6	1.5 (2)	S1—N1—C8—C9	−95.1 (3)
C6—C1—C2—C3	0.2 (4)	N1—C8—C9—C14	131.0 (3)
S1—C1—C2—C3	−178.3 (2)	N1—C8—C9—C10	−51.0 (4)
C1—C2—C3—C4	−0.9 (4)	C14—C9—C10—C11	0.9 (6)
C2—C3—C4—C5	0.7 (5)	C8—C9—C10—C11	−177.2 (4)
C3—C4—C5—C6	0.1 (4)	C9—C10—C11—C12	0.1 (7)
C4—C5—C6—C1	−0.8 (4)	C10—C11—C12—C13	−0.8 (6)
C4—C5—C6—C7	178.7 (3)	C10—C11—C12—Cl1	179.3 (3)
C2—C1—C6—C5	0.6 (4)	C11—C12—C13—C14	0.3 (5)
S1—C1—C6—C5	179.4 (2)	Cl1—C12—C13—C14	−179.8 (2)
C2—C1—C6—C7	−178.9 (2)	C12—C13—C14—C9	0.9 (5)
S1—C1—C6—C7	−0.2 (3)	C10—C9—C14—C13	−1.4 (5)
C8—N1—C7—O3	−3.8 (4)	C8—C9—C14—C13	176.7 (3)
S1—N1—C7—O3	−177.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O3^i	0.93	2.39	3.300 (4)	165

Symmetry code: (i) x, y+1, z.