N-(p-Methoxy­phenyl­sulfan­yl)phthalimide

In the mol­ecule of the title compound, C₁₅H₁₁NO₃S, the dihedral angle between the phthalimide ring system and the benzene ring is 74.07 (8)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.105
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =      15.55
            Cell volume su given      =      13.00
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.68 mm
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         900 Deg.
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C13

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
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
   5 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   5 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
   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-(p-Methoxyphenylsulfanyl)phthalimide

Crystal data

C15H11NO3S	Z = 2
Mr = 285.31	F(000) = 296
Triclinic, P1	Dx = 1.396 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2600 (9) Å	Cell parameters from 13815 reflections
b = 8.4479 (10) Å	θ = 2.7–28.0°
c = 11.4776 (13) Å	µ = 0.24 mm^−1
α = 109.586 (9)°	T = 293 K
β = 93.093 (9)°	Plate, yellow
γ = 112.998 (9)°	0.68 × 0.38 × 0.03 mm
V = 678.61 (13) Å^3

Data collection

Stoe IPDS-2 diffractometer	3185 independent reflections
Radiation source: fine-focus sealed tube	2443 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 6.67 pixels mm^-1	θmax = 27.8°, θmin = 2.7°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→11
Tmin = 0.895, Tmax = 0.990	l = −15→14
10429 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0376P)^2 + 0.1535P] where P = (Fo^2 + 2Fc^2)/3
3185 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.23 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
C1	0.4144 (3)	−0.1867 (3)	0.67768 (18)	0.0558 (4)
C2	0.3187 (2)	−0.3709 (2)	0.57289 (17)	0.0506 (4)
C3	0.3076 (3)	−0.5418 (3)	0.5630 (2)	0.0664 (5)
H3	0.3654	−0.5553	0.6284	0.080*
C4	0.2068 (3)	−0.6930 (3)	0.4518 (2)	0.0720 (6)
H4	0.1967	−0.8105	0.4423	0.086*
C5	0.1208 (3)	−0.6734 (3)	0.3545 (2)	0.0691 (6)
H5	0.0538	−0.7776	0.2809	0.083*
C6	0.1331 (3)	−0.5008 (3)	0.36490 (18)	0.0599 (5)
H6	0.0763	−0.4865	0.2995	0.072*
C7	0.2322 (2)	−0.3518 (2)	0.47553 (16)	0.0473 (4)
C8	0.2695 (2)	−0.1538 (2)	0.51383 (16)	0.0499 (4)
C9	0.3100 (3)	0.1927 (2)	0.81749 (17)	0.0528 (4)
C10	0.1468 (3)	0.1829 (3)	0.77111 (17)	0.0554 (4)
H10	0.1158	0.1608	0.6862	0.066*
C11	0.0296 (3)	0.2055 (3)	0.84908 (17)	0.0565 (4)
H11	−0.0808	0.1962	0.8165	0.068*
C12	0.0768 (3)	0.2420 (3)	0.97576 (17)	0.0610 (5)
C13	0.2396 (3)	0.2512 (4)	1.0224 (2)	0.0854 (8)
H13	0.2715	0.2750	1.1076	0.103*
C14	0.3539 (3)	0.2258 (4)	0.9442 (2)	0.0764 (6)
H14	0.4623	0.2307	0.9763	0.092*
C15	−0.1962 (3)	0.2593 (4)	1.0200 (2)	0.0830 (7)
H15A	−0.2527	0.2839	1.0906	0.124*
H15B	−0.2701	0.1362	0.9580	0.124*
H15C	−0.1817	0.3491	0.9829	0.124*
N1	0.3781 (2)	−0.0616 (2)	0.63636 (14)	0.0519 (3)
O1	0.5043 (2)	−0.1442 (2)	0.77865 (15)	0.0841 (5)
O2	0.2202 (2)	−0.0804 (2)	0.45546 (14)	0.0729 (4)
O3	−0.0244 (2)	0.2724 (3)	1.06214 (13)	0.0872 (5)
S1	0.46624 (7)	0.17248 (7)	0.72051 (5)	0.06249 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0565 (10)	0.0662 (11)	0.0534 (10)	0.0313 (9)	0.0152 (8)	0.0273 (9)
C2	0.0533 (9)	0.0558 (10)	0.0568 (10)	0.0303 (8)	0.0211 (8)	0.0288 (8)
C3	0.0729 (13)	0.0702 (13)	0.0824 (14)	0.0423 (11)	0.0267 (11)	0.0453 (12)
C4	0.0836 (15)	0.0524 (11)	0.0976 (17)	0.0372 (11)	0.0384 (13)	0.0376 (12)
C5	0.0809 (14)	0.0497 (10)	0.0694 (13)	0.0234 (10)	0.0275 (11)	0.0186 (9)
C6	0.0734 (12)	0.0572 (10)	0.0503 (10)	0.0278 (9)	0.0182 (9)	0.0224 (8)
C7	0.0532 (9)	0.0497 (9)	0.0476 (9)	0.0262 (7)	0.0198 (7)	0.0230 (7)
C8	0.0592 (10)	0.0534 (9)	0.0467 (9)	0.0292 (8)	0.0186 (8)	0.0240 (8)
C9	0.0566 (10)	0.0475 (9)	0.0512 (10)	0.0236 (8)	0.0126 (8)	0.0142 (7)
C10	0.0623 (11)	0.0564 (10)	0.0454 (9)	0.0254 (9)	0.0059 (8)	0.0186 (8)
C11	0.0523 (10)	0.0616 (11)	0.0518 (10)	0.0275 (8)	0.0003 (8)	0.0161 (8)
C12	0.0529 (10)	0.0753 (12)	0.0474 (10)	0.0335 (9)	0.0055 (8)	0.0092 (9)
C13	0.0696 (14)	0.147 (2)	0.0436 (11)	0.0644 (15)	0.0065 (9)	0.0221 (13)
C14	0.0614 (12)	0.1166 (19)	0.0561 (12)	0.0541 (13)	0.0079 (9)	0.0215 (12)
C15	0.0536 (12)	0.1064 (18)	0.0754 (15)	0.0405 (12)	0.0114 (10)	0.0129 (13)
N1	0.0596 (9)	0.0496 (8)	0.0491 (8)	0.0268 (7)	0.0141 (7)	0.0180 (6)
O1	0.0905 (11)	0.0909 (11)	0.0665 (10)	0.0399 (9)	−0.0082 (8)	0.0286 (8)
O2	0.1046 (12)	0.0642 (8)	0.0645 (9)	0.0455 (8)	0.0108 (8)	0.0325 (7)
O3	0.0616 (9)	0.1410 (15)	0.0505 (8)	0.0570 (10)	0.0085 (7)	0.0120 (9)
S1	0.0624 (3)	0.0512 (3)	0.0642 (3)	0.0194 (2)	0.0228 (2)	0.0160 (2)

Geometric parameters (Å, º)

C1—O1	1.201 (2)	C9—C14	1.384 (3)
C1—N1	1.414 (2)	C9—S1	1.7700 (19)
C1—C2	1.475 (3)	C10—C11	1.377 (3)
C2—C3	1.376 (3)	C10—H10	0.9300
C2—C7	1.382 (2)	C11—C12	1.380 (3)
C3—C4	1.384 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—O3	1.354 (2)
C4—C5	1.382 (3)	C12—C13	1.383 (3)
C4—H4	0.9300	C13—C14	1.365 (3)
C5—C6	1.385 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.370 (3)	C15—O3	1.424 (3)
C6—H6	0.9300	C15—H15A	0.9600
C7—C8	1.475 (2)	C15—H15B	0.9600
C8—O2	1.202 (2)	C15—H15C	0.9600
C8—N1	1.405 (2)	N1—S1	1.7004 (15)
C9—C10	1.383 (3)
O1—C1—N1	124.98 (19)	C11—C10—C9	120.89 (17)
O1—C1—C2	129.63 (18)	C11—C10—H10	119.6
N1—C1—C2	105.39 (15)	C9—C10—H10	119.6
C3—C2—C7	121.13 (18)	C10—C11—C12	119.71 (17)
C3—C2—C1	129.92 (18)	C10—C11—H11	120.1
C7—C2—C1	108.95 (15)	C12—C11—H11	120.1
C2—C3—C4	117.2 (2)	O3—C12—C11	125.06 (17)
C2—C3—H3	121.4	O3—C12—C13	115.36 (17)
C4—C3—H3	121.4	C11—C12—C13	119.57 (18)
C5—C4—C3	121.49 (19)	C14—C13—C12	120.41 (19)
C5—C4—H4	119.3	C14—C13—H13	119.8
C3—C4—H4	119.3	C12—C13—H13	119.8
C4—C5—C6	120.9 (2)	C13—C14—C9	120.67 (19)
C4—C5—H5	119.5	C13—C14—H14	119.7
C6—C5—H5	119.5	C9—C14—H14	119.7
C7—C6—C5	117.31 (19)	O3—C15—H15A	109.5
C7—C6—H6	121.3	O3—C15—H15B	109.5
C5—C6—H6	121.3	H15A—C15—H15B	109.5
C6—C7—C2	121.88 (16)	O3—C15—H15C	109.5
C6—C7—C8	129.68 (16)	H15A—C15—H15C	109.5
C2—C7—C8	108.44 (15)	H15B—C15—H15C	109.5
O2—C8—N1	125.16 (17)	C8—N1—C1	111.28 (15)
O2—C8—C7	128.90 (17)	C8—N1—S1	124.43 (12)
N1—C8—C7	105.93 (14)	C1—N1—S1	124.17 (13)
C10—C9—C14	118.73 (17)	C12—O3—C15	118.39 (17)
C10—C9—S1	121.70 (14)	N1—S1—C9	102.52 (8)
C14—C9—S1	119.53 (15)
O1—C1—C2—C3	−0.3 (3)	C10—C11—C12—O3	177.89 (19)
N1—C1—C2—C3	−179.64 (18)	C10—C11—C12—C13	−1.5 (3)
O1—C1—C2—C7	179.7 (2)	O3—C12—C13—C14	−179.0 (2)
N1—C1—C2—C7	0.37 (19)	C11—C12—C13—C14	0.5 (4)
C7—C2—C3—C4	0.1 (3)	C12—C13—C14—C9	0.8 (4)
C1—C2—C3—C4	−179.90 (18)	C10—C9—C14—C13	−1.0 (4)
C2—C3—C4—C5	0.1 (3)	S1—C9—C14—C13	176.7 (2)
C3—C4—C5—C6	0.2 (3)	O2—C8—N1—C1	−179.09 (18)
C4—C5—C6—C7	−0.5 (3)	C7—C8—N1—C1	0.82 (19)
C5—C6—C7—C2	0.6 (3)	O2—C8—N1—S1	−2.9 (3)
C5—C6—C7—C8	179.92 (17)	C7—C8—N1—S1	177.05 (11)
C3—C2—C7—C6	−0.5 (3)	O1—C1—N1—C8	179.84 (19)
C1—C2—C7—C6	179.54 (16)	C2—C1—N1—C8	−0.7 (2)
C3—C2—C7—C8	−179.87 (16)	O1—C1—N1—S1	3.6 (3)
C1—C2—C7—C8	0.12 (19)	C2—C1—N1—S1	−176.99 (11)
C6—C7—C8—O2	0.0 (3)	C11—C12—O3—C15	2.5 (3)
C2—C7—C8—O2	179.34 (19)	C13—C12—O3—C15	−178.1 (2)
C6—C7—C8—N1	−179.92 (18)	C8—N1—S1—C9	96.92 (15)
C2—C7—C8—N1	−0.57 (19)	C1—N1—S1—C9	−87.33 (16)
C14—C9—C10—C11	0.0 (3)	C10—C9—S1—N1	−78.45 (16)
S1—C9—C10—C11	−177.71 (14)	C14—C9—S1—N1	103.88 (18)
C9—C10—C11—C12	1.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2^i	0.93	2.42	3.332 (3)	168
C15—H15B···O1^ii	0.96	2.49	3.428 (3)	166

Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z.