4-(3-Methoxy­phenyl­sulfanyl)­phthalo­nitrile

The title compound, C₁₅H₁₀N₂OS, is composed of a 3-methoxy­phenyl­sulfanyl moiety connected via the S atom to a phthalo­nitrile group. The crystal structure is stabilized by C—H...N and C—H...O intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.057
• wR factor = 0.159
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.61 mm
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         S1
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C8     ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C3     ...       1.43 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            N1  -C1  -C8  -C7    129.00100.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         20
            N1  -C1  -C8  -C3    -52.00100.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         32
            C4  -C3  -C2  -N2    -45.00 24.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         33
            C8  -C3  -C2  -N2    136.00 24.00   1.555   1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C15 H10 N2 O S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   5 ALERT type 4 Improvement, methodology, query or suggestion

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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: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

4-(3-Methoxyphenylsulfanyl)phthalonitrile

Crystal data

C15H10N2OS	Z = 2
Mr = 266.31	F(000) = 276
Triclinic, P1	Dx = 1.334 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5982 (9) Å	Cell parameters from 13254 reflections
b = 8.5208 (11) Å	θ = 2.7–29.0°
c = 11.6213 (14) Å	µ = 0.24 mm^−1
α = 101.059 (10)°	T = 293 K
β = 96.146 (9)°	Plate, pale yellow
γ = 113.501 (9)°	0.61 × 0.34 × 0.08 mm
V = 662.94 (14) Å^3

Data collection

Stoe IPDS-2 diffractometer	2591 independent reflections
Radiation source: fine-focus sealed tube	1714 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.7°
ω scans	h = −9→9
Absorption correction: integration (X-SHAPE; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.898, Tmax = 0.978	l = −14→14
8721 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.099P)^2] where P = (Fo^2 + 2Fc^2)/3
2591 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.28 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
C15	0.2353 (5)	−0.2620 (4)	0.5611 (3)	0.0657 (8)
H15A	0.2588	−0.3180	0.6215	0.099*
H15B	0.3107	−0.2730	0.5013	0.099*
H15C	0.0985	−0.3182	0.5245	0.099*
O1	0.2920 (3)	−0.0792 (2)	0.61444 (16)	0.0604 (5)
N1	−0.0509 (6)	−0.5208 (4)	−0.2571 (3)	0.0976 (11)
C10	0.1757 (4)	−0.0430 (3)	0.4232 (2)	0.0502 (6)
H10	0.1256	−0.1633	0.3864	0.060*
C11	0.2693 (4)	0.0225 (3)	0.5425 (2)	0.0492 (6)
S1	0.01873 (12)	−0.00856 (12)	0.21001 (7)	0.0686 (3)
C1	0.0326 (5)	−0.4249 (4)	−0.1668 (3)	0.0706 (9)
C9	0.1579 (4)	0.0739 (4)	0.3594 (2)	0.0526 (6)
C7	0.0466 (4)	−0.2233 (4)	0.0164 (2)	0.0591 (7)
H7	−0.0830	−0.2470	−0.0117	0.071*
C12	0.3396 (4)	0.2019 (3)	0.5965 (2)	0.0575 (7)
H12	0.4004	0.2460	0.6770	0.069*
C14	0.2317 (4)	0.2532 (4)	0.4128 (3)	0.0602 (7)
H14	0.2217	0.3309	0.3690	0.072*
C6	0.1467 (4)	−0.1071 (3)	0.1287 (2)	0.0531 (6)
C8	0.1393 (4)	−0.3029 (4)	−0.0525 (2)	0.0586 (7)
C13	0.3201 (4)	0.3139 (4)	0.5321 (3)	0.0621 (7)
H13	0.3676	0.4337	0.5696	0.075*
C5	0.3414 (4)	−0.0725 (4)	0.1681 (3)	0.0615 (7)
H5	0.4100	0.0061	0.2422	0.074*
C3	0.3350 (5)	−0.2681 (4)	−0.0125 (3)	0.0632 (7)
C4	0.4331 (5)	−0.1523 (4)	0.0997 (3)	0.0674 (8)
H4	0.5624	−0.1291	0.1284	0.081*
C2	0.4323 (6)	−0.3508 (5)	−0.0842 (3)	0.0835 (10)
N2	0.5123 (7)	−0.4143 (6)	−0.1409 (4)	0.1195 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C15	0.076 (2)	0.0599 (16)	0.0653 (18)	0.0337 (15)	0.0116 (15)	0.0157 (13)
O1	0.0702 (12)	0.0548 (10)	0.0474 (10)	0.0237 (9)	−0.0020 (9)	0.0084 (8)
N1	0.129 (3)	0.0753 (18)	0.0602 (17)	0.0328 (18)	−0.0084 (17)	−0.0043 (14)
C10	0.0489 (14)	0.0496 (13)	0.0455 (13)	0.0192 (11)	0.0054 (11)	0.0040 (10)
C11	0.0457 (13)	0.0513 (14)	0.0454 (13)	0.0183 (11)	0.0082 (11)	0.0070 (10)
S1	0.0678 (5)	0.0949 (6)	0.0481 (4)	0.0449 (4)	0.0025 (3)	0.0123 (4)
C1	0.089 (2)	0.0597 (17)	0.0505 (16)	0.0258 (16)	0.0025 (15)	0.0073 (13)
C9	0.0519 (15)	0.0616 (15)	0.0425 (13)	0.0250 (12)	0.0079 (11)	0.0088 (11)
C7	0.0574 (16)	0.0658 (16)	0.0453 (14)	0.0214 (14)	−0.0025 (12)	0.0132 (12)
C12	0.0564 (16)	0.0556 (15)	0.0483 (14)	0.0174 (12)	0.0077 (12)	0.0027 (12)
C14	0.0630 (17)	0.0547 (15)	0.0667 (17)	0.0266 (13)	0.0153 (14)	0.0201 (13)
C6	0.0581 (16)	0.0569 (14)	0.0419 (13)	0.0219 (12)	0.0056 (11)	0.0164 (11)
C8	0.0699 (18)	0.0557 (15)	0.0439 (13)	0.0222 (13)	0.0051 (13)	0.0131 (11)
C13	0.0646 (18)	0.0465 (14)	0.0629 (17)	0.0169 (13)	0.0102 (14)	0.0037 (12)
C5	0.0561 (16)	0.0734 (18)	0.0475 (14)	0.0241 (14)	0.0030 (12)	0.0112 (13)
C3	0.073 (2)	0.0682 (18)	0.0492 (15)	0.0311 (15)	0.0133 (14)	0.0148 (13)
C4	0.0596 (18)	0.087 (2)	0.0516 (16)	0.0314 (16)	0.0075 (13)	0.0125 (14)
C2	0.096 (3)	0.096 (3)	0.062 (2)	0.050 (2)	0.0145 (19)	0.0098 (17)
N2	0.131 (3)	0.137 (3)	0.097 (3)	0.078 (3)	0.031 (2)	−0.001 (2)

Geometric parameters (Å, º)

C15—O1	1.426 (3)	C7—C6	1.397 (4)
C15—H15A	0.9600	C7—H7	0.9300
C15—H15B	0.9600	C12—C13	1.361 (4)
C15—H15C	0.9600	C12—H12	0.9300
O1—C11	1.358 (3)	C14—C13	1.375 (4)
N1—C1	1.134 (4)	C14—H14	0.9300
C10—C11	1.384 (3)	C6—C5	1.393 (4)
C10—C9	1.389 (4)	C8—C3	1.401 (4)
C10—H10	0.9300	C13—H13	0.9300
C11—C12	1.387 (4)	C5—C4	1.368 (4)
S1—C6	1.757 (3)	C5—H5	0.9300
S1—C9	1.781 (3)	C3—C4	1.394 (4)
C1—C8	1.439 (4)	C3—C2	1.435 (5)
C9—C14	1.383 (4)	C4—H4	0.9300
C7—C8	1.375 (4)	C2—N2	1.144 (5)
O1—C15—H15A	109.5	C11—C12—H12	119.8
O1—C15—H15B	109.5	C13—C14—C9	118.5 (3)
H15A—C15—H15B	109.5	C13—C14—H14	120.8
O1—C15—H15C	109.5	C9—C14—H14	120.8
H15A—C15—H15C	109.5	C5—C6—C7	118.8 (3)
H15B—C15—H15C	109.5	C5—C6—S1	124.0 (2)
C11—O1—C15	118.1 (2)	C7—C6—S1	117.2 (2)
C11—C10—C9	118.9 (2)	C7—C8—C3	121.0 (3)
C11—C10—H10	120.5	C7—C8—C1	119.3 (3)
C9—C10—H10	120.5	C3—C8—C1	119.7 (3)
O1—C11—C10	124.2 (2)	C12—C13—C14	121.3 (3)
O1—C11—C12	116.1 (2)	C12—C13—H13	119.4
C10—C11—C12	119.6 (2)	C14—C13—H13	119.4
C6—S1—C9	104.59 (13)	C4—C5—C6	121.0 (3)
N1—C1—C8	179.7 (5)	C4—C5—H5	119.5
C14—C9—C10	121.3 (2)	C6—C5—H5	119.5
C14—C9—S1	118.5 (2)	C4—C3—C8	118.4 (3)
C10—C9—S1	120.0 (2)	C4—C3—C2	120.5 (3)
C8—C7—C6	120.1 (3)	C8—C3—C2	121.2 (3)
C8—C7—H7	119.9	C5—C4—C3	120.7 (3)
C6—C7—H7	119.9	C5—C4—H4	119.6
C13—C12—C11	120.4 (3)	C3—C4—H4	119.6
C13—C12—H12	119.8	N2—C2—C3	179.0 (5)
C15—O1—C11—C10	7.2 (4)	C6—C7—C8—C1	178.8 (3)
C15—O1—C11—C12	−175.4 (3)	N1—C1—C8—C7	129 (100)
C9—C10—C11—O1	178.6 (2)	N1—C1—C8—C3	−52 (100)
C9—C10—C11—C12	1.3 (4)	C11—C12—C13—C14	−0.2 (5)
C11—C10—C9—C14	0.1 (4)	C9—C14—C13—C12	1.5 (4)
C11—C10—C9—S1	−174.2 (2)	C7—C6—C5—C4	−1.0 (4)
C6—S1—C9—C14	121.1 (2)	S1—C6—C5—C4	−179.3 (2)
C6—S1—C9—C10	−64.5 (3)	C7—C8—C3—C4	0.8 (4)
O1—C11—C12—C13	−178.8 (3)	C1—C8—C3—C4	−178.6 (3)
C10—C11—C12—C13	−1.2 (4)	C7—C8—C3—C2	−180.0 (3)
C10—C9—C14—C13	−1.4 (4)	C1—C8—C3—C2	0.7 (4)
S1—C9—C14—C13	172.9 (2)	C6—C5—C4—C3	1.2 (5)
C8—C7—C6—C5	0.7 (4)	C8—C3—C4—C5	−1.1 (5)
C8—C7—C6—S1	179.1 (2)	C2—C3—C4—C5	179.7 (3)
C9—S1—C6—C5	−18.3 (3)	C4—C3—C2—N2	−45 (24)
C9—S1—C6—C7	163.4 (2)	C8—C3—C2—N2	136 (24)
C6—C7—C8—C3	−0.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···N1^i	0.93	2.62	3.534 (4)	167
C5—H5···O1^ii	0.93	2.44	3.191 (3)	138

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