N-[(4-Methylphenyl)sulfan­yl]phthalimide

In the title compound, C₁₅H₁₁NO₂S, the dihedral angle between the two planar ring systems is 74.49 (5)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.109
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.75 mm

Alert level G
PLAT200_ALERT_1_G 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
   1 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
   1 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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 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).

N-[4-Methoxyphenyl)sulfanyl]phthalimide

Crystal data

C15H11NO2S	Z = 2
Mr = 269.31	F(000) = 280
Triclinic, P1	Dx = 1.390 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2186 (8) Å	Cell parameters from 9810 reflections
b = 8.318 (1) Å	θ = 2.6–27.9°
c = 11.5374 (13) Å	µ = 0.25 mm^−1
α = 103.142 (10)°	T = 296 K
β = 99.418 (9)°	Plate, colorless
γ = 101.976 (9)°	0.75 × 0.51 × 0.07 mm
V = 643.57 (13) Å^3

Data collection

Stoe IPDS-2 diffractometer	2979 independent reflections
Radiation source: fine-focus sealed tube	2533 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.079
Detector resolution: 6.67 pixels mm^-1	θmax = 27.7°, θmin = 2.8°
ω scans	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.826, Tmax = 0.980	l = −15→14
9810 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0443P)^2 + 0.1565P] where P = (Fo^2 + 2Fc^2)/3
2979 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.33 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
S1	0.43330 (6)	0.27312 (6)	0.76446 (4)	0.05156 (15)
C1	0.2644 (2)	0.30991 (19)	0.54309 (13)	0.0393 (3)
O2	0.21414 (18)	0.15993 (15)	0.49482 (12)	0.0564 (3)
C2	0.24059 (19)	0.45397 (18)	0.49176 (13)	0.0378 (3)
C13	−0.0888 (2)	0.0513 (2)	0.81456 (16)	0.0510 (4)
H13	−0.1924	−0.0416	0.7719	0.061*
N1	0.36164 (18)	0.38511 (17)	0.66650 (12)	0.0425 (3)
C12	−0.0981 (2)	0.1497 (2)	0.92645 (16)	0.0508 (4)
C14	0.0705 (2)	0.0880 (2)	0.76512 (15)	0.0471 (4)
H14	0.0746	0.0192	0.6902	0.057*
C9	0.2254 (2)	0.2274 (2)	0.82668 (14)	0.0430 (3)
C3	0.1556 (2)	0.4529 (2)	0.37520 (14)	0.0462 (3)
H3	0.1011	0.3511	0.3144	0.055*
C8	0.4000 (2)	0.5646 (2)	0.69621 (15)	0.0458 (3)
C7	0.3215 (2)	0.60551 (19)	0.58249 (14)	0.0408 (3)
O1	0.4804 (2)	0.65918 (19)	0.79486 (12)	0.0726 (4)
C10	0.2189 (3)	0.3271 (2)	0.93855 (16)	0.0578 (4)
H10	0.3222	0.4203	0.9810	0.069*
C5	0.2354 (3)	0.7599 (2)	0.44242 (19)	0.0566 (4)
H5	0.2327	0.8630	0.4244	0.068*
C6	0.3202 (2)	0.7610 (2)	0.55938 (18)	0.0528 (4)
H6	0.3744	0.8628	0.6202	0.063*
C15	−0.2724 (3)	0.1066 (3)	0.9803 (2)	0.0720 (6)
H15A	−0.3657	0.0084	0.9251	0.108*
H15B	−0.3298	0.2017	0.9934	0.108*
H15C	−0.2328	0.0824	1.0567	0.108*
C4	0.1548 (2)	0.6090 (3)	0.35220 (17)	0.0538 (4)
H4	0.0989	0.6121	0.2745	0.065*
C11	0.0585 (3)	0.2878 (3)	0.98704 (17)	0.0637 (5)
H11	0.0551	0.3557	1.0624	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0407 (2)	0.0666 (3)	0.0544 (3)	0.01435 (18)	0.00996 (17)	0.0299 (2)
C1	0.0361 (7)	0.0400 (8)	0.0408 (7)	0.0080 (5)	0.0107 (5)	0.0092 (6)
O2	0.0690 (8)	0.0365 (6)	0.0568 (7)	0.0103 (5)	0.0066 (6)	0.0075 (5)
C2	0.0343 (6)	0.0388 (7)	0.0426 (7)	0.0104 (5)	0.0141 (5)	0.0106 (6)
C13	0.0449 (8)	0.0491 (9)	0.0550 (9)	0.0051 (7)	0.0062 (7)	0.0156 (7)
N1	0.0420 (6)	0.0441 (7)	0.0406 (6)	0.0076 (5)	0.0078 (5)	0.0138 (5)
C12	0.0506 (9)	0.0592 (10)	0.0526 (9)	0.0183 (7)	0.0157 (7)	0.0280 (8)
C14	0.0488 (8)	0.0460 (9)	0.0433 (8)	0.0094 (7)	0.0077 (6)	0.0099 (7)
C9	0.0419 (7)	0.0492 (8)	0.0389 (7)	0.0094 (6)	0.0057 (6)	0.0180 (6)
C3	0.0451 (8)	0.0514 (9)	0.0434 (8)	0.0149 (7)	0.0108 (6)	0.0122 (7)
C8	0.0438 (8)	0.0451 (8)	0.0440 (8)	0.0064 (6)	0.0111 (6)	0.0066 (6)
C7	0.0370 (7)	0.0400 (7)	0.0455 (8)	0.0093 (6)	0.0141 (6)	0.0089 (6)
O1	0.0867 (10)	0.0630 (9)	0.0469 (7)	0.0064 (7)	−0.0022 (6)	−0.0033 (6)
C10	0.0586 (10)	0.0572 (10)	0.0434 (9)	−0.0028 (8)	0.0051 (7)	0.0060 (8)
C5	0.0572 (10)	0.0500 (10)	0.0775 (12)	0.0225 (8)	0.0246 (9)	0.0317 (9)
C6	0.0526 (9)	0.0382 (8)	0.0673 (11)	0.0116 (7)	0.0198 (8)	0.0090 (7)
C15	0.0661 (12)	0.0951 (17)	0.0777 (14)	0.0301 (11)	0.0350 (11)	0.0461 (13)
C4	0.0523 (9)	0.0654 (11)	0.0558 (10)	0.0241 (8)	0.0170 (7)	0.0285 (9)
C11	0.0761 (12)	0.0686 (12)	0.0416 (9)	0.0117 (10)	0.0198 (8)	0.0069 (8)

Geometric parameters (Å, º)

S1—N1	1.7030 (13)	C3—C4	1.384 (2)
S1—C9	1.7752 (16)	C3—H3	0.9300
C1—O2	1.1950 (19)	C8—O1	1.199 (2)
C1—N1	1.4132 (19)	C8—C7	1.483 (2)
C1—C2	1.480 (2)	C7—C6	1.380 (2)
C2—C3	1.381 (2)	C10—C11	1.378 (3)
C2—C7	1.386 (2)	C10—H10	0.9300
C13—C14	1.375 (2)	C5—C4	1.379 (3)
C13—C12	1.383 (3)	C5—C6	1.385 (3)
C13—H13	0.9300	C5—H5	0.9300
N1—C8	1.410 (2)	C6—H6	0.9300
C12—C11	1.387 (3)	C15—H15A	0.9600
C12—C15	1.506 (2)	C15—H15B	0.9600
C14—C9	1.388 (2)	C15—H15C	0.9600
C14—H14	0.9300	C4—H4	0.9300
C9—C10	1.380 (2)	C11—H11	0.9300
N1—S1—C9	101.59 (7)	O1—C8—C7	129.27 (16)
O2—C1—N1	124.95 (14)	N1—C8—C7	105.76 (13)
O2—C1—C2	129.46 (14)	C6—C7—C2	121.07 (15)
N1—C1—C2	105.59 (13)	C6—C7—C8	130.46 (15)
C3—C2—C7	121.33 (15)	C2—C7—C8	108.46 (13)
C3—C2—C1	129.89 (14)	C11—C10—C9	119.62 (16)
C7—C2—C1	108.79 (13)	C11—C10—H10	120.2
C14—C13—C12	121.28 (16)	C9—C10—H10	120.2
C14—C13—H13	119.4	C4—C5—C6	121.23 (16)
C12—C13—H13	119.4	C4—C5—H5	119.4
C8—N1—C1	111.40 (13)	C6—C5—H5	119.4
C8—N1—S1	124.44 (11)	C7—C6—C5	117.63 (16)
C1—N1—S1	124.08 (11)	C7—C6—H6	121.2
C13—C12—C11	117.75 (16)	C5—C6—H6	121.2
C13—C12—C15	120.74 (18)	C12—C15—H15A	109.5
C11—C12—C15	121.51 (18)	C12—C15—H15B	109.5
C13—C14—C9	120.18 (15)	H15A—C15—H15B	109.5
C13—C14—H14	119.9	C12—C15—H15C	109.5
C9—C14—H14	119.9	H15A—C15—H15C	109.5
C10—C9—C14	119.38 (15)	H15B—C15—H15C	109.5
C10—C9—S1	120.25 (13)	C5—C4—C3	121.25 (16)
C14—C9—S1	120.34 (12)	C5—C4—H4	119.4
C2—C3—C4	117.49 (16)	C3—C4—H4	119.4
C2—C3—H3	121.3	C10—C11—C12	121.76 (17)
C4—C3—H3	121.3	C10—C11—H11	119.1
O1—C8—N1	124.97 (16)	C12—C11—H11	119.1
O2—C1—C2—C3	−0.4 (3)	C1—N1—C8—C7	−0.24 (16)
N1—C1—C2—C3	179.90 (14)	S1—N1—C8—C7	176.84 (10)
O2—C1—C2—C7	179.75 (15)	C3—C2—C7—C6	−0.1 (2)
N1—C1—C2—C7	0.06 (15)	C1—C2—C7—C6	179.74 (13)
O2—C1—N1—C8	−179.58 (14)	C3—C2—C7—C8	179.94 (13)
C2—C1—N1—C8	0.12 (16)	C1—C2—C7—C8	−0.21 (16)
O2—C1—N1—S1	3.3 (2)	O1—C8—C7—C6	0.3 (3)
C2—C1—N1—S1	−176.97 (9)	N1—C8—C7—C6	−179.67 (15)
C9—S1—N1—C8	93.66 (13)	O1—C8—C7—C2	−179.73 (17)
C9—S1—N1—C1	−89.62 (13)	N1—C8—C7—C2	0.28 (16)
C14—C13—C12—C11	0.4 (3)	C14—C9—C10—C11	−0.5 (3)
C14—C13—C12—C15	−179.19 (16)	S1—C9—C10—C11	−178.52 (15)
C12—C13—C14—C9	−0.8 (3)	C2—C7—C6—C5	0.0 (2)
C13—C14—C9—C10	0.9 (2)	C8—C7—C6—C5	179.92 (15)
C13—C14—C9—S1	178.91 (12)	C4—C5—C6—C7	0.1 (3)
N1—S1—C9—C10	−98.24 (15)	C6—C5—C4—C3	0.0 (3)
N1—S1—C9—C14	83.73 (14)	C2—C3—C4—C5	−0.2 (2)
C7—C2—C3—C4	0.2 (2)	C9—C10—C11—C12	0.1 (3)
C1—C2—C3—C4	−179.62 (14)	C13—C12—C11—C10	0.0 (3)
C1—N1—C8—O1	179.77 (16)	C15—C12—C11—C10	179.57 (19)
S1—N1—C8—O1	−3.2 (2)