4-Methyl-N-(3-oxo-1,3-dihydro­iso­benzo­furan-1-yl)benzene­sulfonamide

Odabaşoğlu, M.; Büyükgüngör, O.

doi:10.1107/S1600536807057595

4-Methyl-N-(3-oxo-1,3-dihydroisobenzofuran-1-yl)benzenesulfonamide

M. Odabaşoğlu and O. Büyükgüngör

The title compound, C₁₅H₁₃NO₄S, exhibits N—H

O and C—H

O hydrogen-bond interactions that generate S(5) and R₂²(9) ring motifs arranged as molecular chains along the c axis. The phthalide part of the molecule is planar and is inclined by 67.66 (12)° to the substituted aromatic ring.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057595/sj2415sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057595/sj2415Isup2.hkl Contains datablock I

CCDC reference: 672955

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.041
wR factor = 0.110
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.78 mm
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               2758
           Count of symmetry unique reflns         1471
           Completeness (_total/calc)            187.49%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1287
           Fraction of Friedel pairs measured     0.875
           Are heavy atom types Z>Si present        yes
PLAT792_ALERT_1_G Check the Absolute Configuration of C8     = ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   3 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Phthalides are known to show diverse biological activities as hormones, pheromones and antibiotics (Aoki et al., 1973; Kubota & Tatsuno, 1971; Tsi & Tan, 1997). As part of our on going research on 3-substituted phthalides, the title compound, (I), has been synthesized and its crystal structure is reported here.

The molecule of (I) is built up from a phthalide unit connected to a p-toluensulfonyl group through an amino group (Fig. 1). The phthalide part (atoms C1–C8) is essentially planar, the largest deviation from the mean plane being -0.065 (3) Å for atom C8. The dihedral angle between the substituted aromatic ring and the mean plane of the phthalide group is 67.66 (12)°. In (I), the crystal packing is stabilized by N—H···O and C—H···O hydrogen bond interactions that these interactions generate S(5) and R₂²(9) ring motifs (Bernstein et al., 1995; Etter, 1990). These motifs are arranged in the molecular chains along the c axis (Fig. 2, 3 and Table 1).

Related literature top

For related structures (3-halogenophenyl phthalides, halogens = I, Br, Cl, F), see: Büyükgüngör & Odabaşoğlu (2006); Odabaşoğlu & Büyükgüngör (2007a, 2007b; 2006). For ring motif details, see: Bernstein et al. (1995); Etter (1990). For general background, see: Aoki et al. (1973); Lacova (1973); Elderfield (1951); Tsi & Tan (1997); Bellasio (1974); Roy & Sarkar (2005); Kubota & Tatsuno (1971). [Please note that the Related literature section must contain all those references, and only those references, that are cited elsewhere in the CIF. References Büyükgüngör & Odabaşoğlu (2006), Odabaşoğlu & Büyükgüngör (2007a), Lacova (1973), Elderfield (1951), Bellasio (1974) and Roy & Sarkar (2005) are not cited anywhere in the CIF. Please provide revised text which includes them or they will be removed]

Experimental top

The title compound was prepared according to the method described by Odabaşoğlu & Büyükgüngör (2006), using phthalaldehydic acid and 2-bromoaniline as starting materials (yield 70%; m.p. 430–432 K). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol–DMF (v/v, 1/1) solution at room temperature.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (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).

Figures top

	Fig. 1. A view of (I) with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The intramolecular hydrogen bond is drawn as a dashed line.
	Fig. 2. Part of the crystal structure of (I), showing the formation of S(5) and R₂²(9) ring motifs. H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry codes: (i) 1 - x, -y, z + 1/2; (ii) 1 - x, -y, z - 1/2].
	Fig. 3. A packing diagram of (I), with hydrogen bonds drawn as dashed lines. H atoms not involved in hydrogen bonds have been omitted for clarity.

4-Methyl-N-(3-oxo-1,3-dihydroisobenzofuran-1-yl)benzenesulfonamide top

Crystal data top

C₁₅H₁₃NO₄S	F(000) = 632
M_r = 303.32	D_x = 1.440 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 11123 reflections
a = 17.6356 (14) Å	θ = 2.2–27.1°
b = 8.4593 (6) Å	µ = 0.25 mm⁻¹
c = 9.3809 (6) Å	T = 296 K
V = 1399.49 (17) Å³	Block, colorless
Z = 4	0.78 × 0.68 × 0.52 mm

Data collection top

Stoe IPDS II diffractometer	2758 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2262 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.063
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.3°
ω scan rotation method	h = −21→21
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
T_min = 0.850, T_max = 0.898	l = −11→11
11123 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0758P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
2758 reflections	Δρ_max = 0.17 e Å⁻³
193 parameters	Δρ_min = −0.28 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with 1287 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.08 (9)

Crystal data top

C₁₅H₁₃NO₄S	V = 1399.49 (17) Å³
M_r = 303.32	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 17.6356 (14) Å	µ = 0.25 mm⁻¹
b = 8.4593 (6) Å	T = 296 K
c = 9.3809 (6) Å	0.78 × 0.68 × 0.52 mm

Data collection top

Stoe IPDS II diffractometer	2758 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2262 reflections with I > 2σ(I)
T_min = 0.850, T_max = 0.898	R_int = 0.063
11123 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	Δρ_max = 0.17 e Å⁻³
S = 0.98	Δρ_min = −0.28 e Å⁻³
2758 reflections	Absolute structure: Flack (1983), with 1287 Friedel pairs
193 parameters	Absolute structure parameter: −0.08 (9)
1 restraint

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	U_iso*/U_eq
C1	0.50446 (16)	0.1283 (3)	0.6188 (3)	0.0549 (6)
C2	0.42320 (17)	0.1352 (3)	0.6529 (3)	0.0548 (6)
C3	0.38379 (19)	0.0680 (4)	0.7648 (3)	0.0704 (8)
H3	0.4081	0.0112	0.8363	0.084*
C4	0.3069 (2)	0.0897 (5)	0.7644 (4)	0.0843 (10)
H4	0.2781	0.0459	0.8375	0.101*
C5	0.27106 (19)	0.1746 (5)	0.6587 (5)	0.0853 (10)
H5	0.2186	0.1858	0.6621	0.102*
C6	0.31076 (17)	0.2436 (4)	0.5477 (3)	0.0712 (8)
H6	0.2866	0.3016	0.4769	0.085*
C7	0.38812 (15)	0.2216 (3)	0.5482 (3)	0.0533 (6)
C8	0.44652 (15)	0.2846 (4)	0.4467 (3)	0.0541 (6)
H8	0.4510	0.3991	0.4601	0.065*
C9	0.55597 (17)	0.3469 (3)	0.1450 (3)	0.0583 (7)
C10	0.57909 (17)	0.2585 (4)	0.0291 (3)	0.0635 (7)
H10	0.5433	0.2155	−0.0326	0.076*
C11	0.65528 (17)	0.2342 (4)	0.0053 (3)	0.0744 (8)
H11	0.6706	0.1751	−0.0732	0.089*
C12	0.7093 (2)	0.2965 (5)	0.0963 (4)	0.0790 (9)
C13	0.68489 (19)	0.3860 (4)	0.2101 (4)	0.0792 (10)
H13	0.7206	0.4296	0.2715	0.095*
C14	0.60886 (19)	0.4129 (4)	0.2355 (3)	0.0710 (8)
H14	0.5936	0.4746	0.3123	0.085*
C15	0.7928 (2)	0.2635 (7)	0.0736 (6)	0.1181 (16)
H15A	0.8217	0.3136	0.1477	0.177*
H15B	0.8082	0.3046	−0.0173	0.177*
H15C	0.8015	0.1515	0.0760	0.177*
N1	0.43189 (14)	0.2530 (3)	0.3006 (2)	0.0565 (5)
O1	0.55549 (11)	0.0622 (2)	0.6801 (3)	0.0732 (6)
O2	0.51692 (10)	0.2083 (2)	0.49564 (18)	0.0565 (5)
O3	0.45049 (14)	0.5308 (3)	0.2340 (3)	0.0826 (7)
O4	0.41807 (13)	0.3302 (3)	0.0519 (2)	0.0806 (7)
S1	0.45901 (4)	0.37722 (8)	0.17674 (8)	0.0604 (2)
H1	0.4318 (19)	0.154 (4)	0.275 (4)	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0634 (17)	0.0530 (14)	0.0484 (12)	−0.0054 (12)	−0.0059 (11)	0.0036 (12)
C2	0.0698 (15)	0.0511 (13)	0.0437 (16)	−0.0015 (11)	0.0050 (11)	−0.0041 (11)
C3	0.086 (2)	0.0747 (19)	0.0501 (15)	−0.0029 (16)	0.0070 (13)	0.0096 (14)
C4	0.084 (2)	0.101 (3)	0.068 (2)	−0.0044 (18)	0.0281 (17)	0.0039 (19)
C5	0.0626 (17)	0.109 (3)	0.084 (2)	0.0072 (15)	0.0189 (18)	−0.013 (2)
C6	0.0687 (18)	0.082 (2)	0.0626 (18)	0.0150 (14)	0.0033 (14)	−0.0082 (15)
C7	0.0611 (14)	0.0559 (14)	0.0429 (12)	0.0031 (12)	0.0042 (11)	−0.0060 (11)
C8	0.0662 (16)	0.0537 (14)	0.0423 (13)	0.0050 (11)	−0.0038 (11)	−0.0034 (11)
C9	0.0696 (17)	0.0575 (15)	0.0479 (18)	−0.0043 (12)	−0.0009 (11)	0.0121 (11)
C10	0.0699 (17)	0.0698 (18)	0.0510 (14)	−0.0009 (14)	−0.0029 (13)	0.0052 (12)
C11	0.0726 (19)	0.091 (2)	0.0599 (17)	0.0042 (16)	0.0078 (15)	0.0041 (16)
C12	0.0708 (19)	0.098 (2)	0.068 (2)	−0.0084 (17)	0.0042 (16)	0.0262 (19)
C13	0.0732 (19)	0.095 (2)	0.069 (2)	−0.0242 (17)	−0.0102 (15)	0.0147 (17)
C14	0.081 (2)	0.074 (2)	0.0571 (15)	−0.0119 (16)	−0.0037 (15)	0.0019 (14)
C15	0.064 (2)	0.183 (5)	0.107 (3)	−0.006 (3)	0.006 (2)	0.030 (3)
N1	0.0689 (13)	0.0603 (14)	0.0403 (11)	0.0019 (12)	−0.0018 (10)	−0.0046 (10)
O1	0.0701 (12)	0.0725 (12)	0.0770 (13)	−0.0017 (9)	−0.0159 (13)	0.0212 (14)
O2	0.0548 (9)	0.0659 (12)	0.0488 (10)	−0.0025 (8)	−0.0037 (8)	0.0062 (9)
O3	0.1074 (18)	0.0654 (13)	0.0748 (14)	0.0200 (11)	0.0085 (12)	0.0102 (11)
O4	0.0702 (13)	0.1198 (19)	0.0519 (11)	0.0065 (12)	−0.0136 (10)	0.0065 (12)
S1	0.0688 (4)	0.0671 (4)	0.0454 (3)	0.0099 (3)	−0.0024 (3)	0.0113 (4)

Geometric parameters (Å, º) top

C1—O1	1.206 (3)	C9—C10	1.381 (4)
C1—O2	1.357 (3)	C9—S1	1.754 (3)
C1—C2	1.469 (4)	C10—C11	1.378 (4)
C2—C7	1.372 (4)	C10—H10	0.9300
C2—C3	1.381 (4)	C11—C12	1.383 (5)
C3—C4	1.368 (5)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.377 (5)
C4—C5	1.378 (6)	C12—C15	1.514 (5)
C4—H4	0.9300	C13—C14	1.381 (5)
C5—C6	1.384 (5)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.377 (4)	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C8	1.501 (4)	C15—H15C	0.9600
C8—N1	1.419 (3)	N1—S1	1.638 (3)
C8—O2	1.473 (3)	N1—H1	0.87 (4)
C8—H8	0.9800	O3—S1	1.414 (3)
C9—C14	1.379 (4)	O4—S1	1.432 (2)

O1—C1—O2	121.1 (3)	C11—C10—H10	120.1
O1—C1—C2	130.0 (3)	C9—C10—H10	120.1
O2—C1—C2	108.9 (2)	C10—C11—C12	120.9 (3)
C7—C2—C3	122.4 (3)	C10—C11—H11	119.5
C7—C2—C1	107.8 (2)	C12—C11—H11	119.5
C3—C2—C1	129.7 (3)	C13—C12—C11	118.2 (3)
C4—C3—C2	116.2 (3)	C13—C12—C15	120.9 (4)
C4—C3—H3	121.9	C11—C12—C15	120.8 (4)
C2—C3—H3	121.9	C12—C13—C14	121.8 (3)
C3—C4—C5	121.8 (3)	C12—C13—H13	119.1
C3—C4—H4	119.1	C14—C13—H13	119.1
C5—C4—H4	119.1	C9—C14—C13	119.0 (3)
C4—C5—C6	121.9 (3)	C9—C14—H14	120.5
C4—C5—H5	119.0	C13—C14—H14	120.5
C6—C5—H5	119.0	C12—C15—H15A	109.5
C7—C6—C5	116.2 (3)	C12—C15—H15B	109.5
C7—C6—H6	121.9	H15A—C15—H15B	109.5
C5—C6—H6	121.9	C12—C15—H15C	109.5
C2—C7—C6	121.4 (3)	H15A—C15—H15C	109.5
C2—C7—C8	109.5 (2)	H15B—C15—H15C	109.5
C6—C7—C8	129.1 (3)	C8—N1—S1	120.7 (2)
N1—C8—O2	111.8 (2)	C8—N1—H1	116 (3)
N1—C8—C7	114.9 (2)	S1—N1—H1	115 (2)
O2—C8—C7	103.0 (2)	C1—O2—C8	110.3 (2)
N1—C8—H8	109.0	O3—S1—O4	120.82 (15)
O2—C8—H8	109.0	O3—S1—N1	106.81 (14)
C7—C8—H8	109.0	O4—S1—N1	104.76 (14)
C14—C9—C10	120.2 (3)	O3—S1—C9	107.59 (14)
C14—C9—S1	119.7 (2)	O4—S1—C9	108.17 (13)
C10—C9—S1	120.0 (2)	N1—S1—C9	108.14 (12)
C11—C10—C9	119.8 (3)

O1—C1—C2—C7	−178.2 (3)	C10—C11—C12—C13	−1.2 (5)
O2—C1—C2—C7	−0.5 (3)	C10—C11—C12—C15	177.3 (4)
O1—C1—C2—C3	0.3 (5)	C11—C12—C13—C14	0.7 (5)
O2—C1—C2—C3	178.0 (3)	C15—C12—C13—C14	−177.8 (4)
C7—C2—C3—C4	1.2 (5)	C10—C9—C14—C13	−1.5 (4)
C1—C2—C3—C4	−177.1 (3)	S1—C9—C14—C13	179.1 (2)
C2—C3—C4—C5	−0.4 (5)	C12—C13—C14—C9	0.6 (5)
C3—C4—C5—C6	−0.5 (6)	O2—C8—N1—S1	−94.8 (3)
C4—C5—C6—C7	0.5 (5)	C7—C8—N1—S1	148.3 (2)
C3—C2—C7—C6	−1.2 (4)	O1—C1—O2—C8	−177.1 (3)
C1—C2—C7—C6	177.4 (3)	C2—C1—O2—C8	4.9 (3)
C3—C2—C7—C8	177.3 (3)	N1—C8—O2—C1	−130.8 (2)
C1—C2—C7—C8	−4.1 (3)	C7—C8—O2—C1	−7.0 (3)
C5—C6—C7—C2	0.3 (4)	C8—N1—S1—O3	−35.7 (3)
C5—C6—C7—C8	−177.9 (3)	C8—N1—S1—O4	−165.0 (2)
C2—C7—C8—N1	128.5 (3)	C8—N1—S1—C9	79.8 (2)
C6—C7—C8—N1	−53.1 (4)	C14—C9—S1—O3	34.3 (3)
C2—C7—C8—O2	6.7 (3)	C10—C9—S1—O3	−145.1 (2)
C6—C7—C8—O2	−175.0 (3)	C14—C9—S1—O4	166.4 (2)
C14—C9—C10—C11	1.0 (4)	C10—C9—S1—O4	−13.1 (3)
S1—C9—C10—C11	−179.6 (2)	C14—C9—S1—N1	−80.7 (3)
C9—C10—C11—C12	0.4 (5)	C10—C9—S1—N1	99.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3	0.98	2.40	2.885 (4)	110
N1—H1···O1ⁱ	0.87 (4)	2.04 (4)	2.904 (3)	168 (3)

Symmetry code: (i) −x+1, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₄S
M_r	303.32
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	17.6356 (14), 8.4593 (6), 9.3809 (6)
V (Å³)	1399.49 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.78 × 0.68 × 0.52

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.850, 0.898
No. of measured, independent and observed [I > 2σ(I)] reflections	11123, 2758, 2262
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.110, 0.98
No. of reflections	2758
No. of parameters	193
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.28
Absolute structure	Flack (1983), with 1287 Friedel pairs
Absolute structure parameter	−0.08 (9)

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).