In the molecule of the title compound, C15H11NO3S, the dihedral angle between the phthalimide ring system and the benzene ring is 74.07 (8)°.
Supporting information
CCDC reference: 636174
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0376P)2 + 0.1535P] where P = (Fo2 + 2Fc2)/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 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 | |
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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.93 | 2.42 | 3.332 (3) | 168 |
C15—H15B···O1ii | 0.96 | 2.49 | 3.428 (3) | 166 |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z. |