Cystal structure of N-[2-(benzo[d][1,3]dioxol-5-yl)eth­yl]-4-methyl­benzene­sulfonamide

Abstract

In the title compound, C₁₆H₁₇NO₄S, the heterocyclic ring is almost planar (r.m.s. deviation = 0.007Å) and the dihedral angle between the benzene rings is 28.18 (10)°. The N—C—C—C torsion angle for the central chain is 62.4 (3)°: overall, the mol­ecule has a Z-shape. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R ₂ ²(8) loops.

Related literature  

For background to methyl­benzene­sulfonamide derivatives, see: Barn et al. (2001 ▸); Ghorai et al. (2010 ▸).

Experimental  

Crystal data  

• C₁₆H₁₇NO₄S

• M _r = 319.37

• Monoclinic,

• a = 12.3265 (2) Å

• b = 9.96026 (16) Å

• c = 12.7021 (3) Å

• β = 100.5980 (18)°

• V = 1532.90 (5) ų

• Z = 4

• Mo Kα radiation

• μ = 0.23 mm⁻¹

• T = 293 K

• 0.40 × 0.20 × 0.12 mm

Data collection  

• Agilent SuperNova (single source at offset), Eos diffractometer

• Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▸) T _min = 0.868, T _max = 1.000

• 12219 measured reflections

• 3136 independent reflections

• 2587 reflections with I > 2σ(I)

• R _int = 0.029

Refinement  

• R[F ² > 2σ(F ²)] = 0.043

• wR(F ²) = 0.115

• S = 1.05

• 3136 reflections

• 204 parameters

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.19 e Å⁻³

• Δρ_min = −0.39 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: OLEX (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX.

Supplementary Material

CCDC reference: 1401539

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N1H1O4i	0.84(2)	2.19(2)	3.026(2)	172(2)

Symmetry code: (i) .

supplementary crystallographic information

S1. Experimental

A solution of sulfonylchloride (10 mmol) in dichloromethane (15 mL) was slowly added to a cooled solution of methylenedioxyphenethylamine (15 mmol) in dichloromethane (10 ml) and triethylamine (15 mmol). Yellow blocks of the title compound were obtained by slow evaporation of a solution in methanol.

S2. 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 > 2sigma(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.

Figures

Fig. 1.

The molecular structure of title compound, with atom labelling. Displacement ellipsoids are drawn at 30% probability level.

Crystal data

C16H17NO4S	F(000) = 672
Mr = 319.37	Dx = 1.384 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 12.3265 (2) Å	Cell parameters from 5283 reflections
b = 9.96026 (16) Å	θ = 2.9–28.7°
c = 12.7021 (3) Å	µ = 0.23 mm−1
β = 100.5980 (18)°	T = 293 K
V = 1532.90 (5) Å3	Block, yellow
Z = 4	0.40 × 0.20 × 0.12 mm

Data collection

Agilent SuperNova (single source at offset), Eos diffractometer	3136 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2587 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 16.1623 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
Tmin = 0.868, Tmax = 1.000	l = −15→15
12219 measured reflections

Refinement

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) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0499P)2 + 0.4898P] where P = (Fo2 + 2Fc2)/3
3136 reflections	(Δ/σ)max < 0.001
204 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.39 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	0.01040 (4)	0.17100 (5)	0.62290 (4)	0.04836 (17)
O1	0.10241 (14)	−0.39697 (19)	0.99233 (14)	0.0834 (5)
O2	0.07337 (17)	−0.43875 (18)	0.81134 (15)	0.0899 (6)
O3	0.04945 (13)	0.23231 (16)	0.72422 (12)	0.0689 (4)
O4	0.08943 (10)	0.12122 (14)	0.56207 (12)	0.0602 (4)
N1	−0.06387 (14)	0.04327 (17)	0.64128 (15)	0.0521 (4)
H1	−0.0777 (17)	−0.003 (2)	0.5849 (18)	0.058 (7)*
C1	0.1333 (2)	−0.4786 (3)	0.9109 (2)	0.0844 (8)
H1A	0.2117	−0.4692	0.9115	0.101*
H1B	0.1181	−0.5721	0.9239	0.101*
C2	0.02598 (17)	−0.3080 (2)	0.93953 (17)	0.0564 (5)
C3	−0.0287 (2)	−0.2082 (3)	0.98013 (18)	0.0725 (7)
H3	−0.0176	−0.1910	1.0533	0.087*
C4	−0.10220 (19)	−0.1330 (2)	0.90745 (18)	0.0657 (6)
H4	−0.1404	−0.0633	0.9331	0.079*
C5	−0.12075 (16)	−0.1574 (2)	0.79891 (16)	0.0515 (5)
C6	−0.06264 (17)	−0.2603 (2)	0.76031 (16)	0.0556 (5)
H6	−0.0725	−0.2786	0.6874	0.067*
C7	0.00883 (17)	−0.3334 (2)	0.83196 (17)	0.0538 (5)
C8	−0.20189 (18)	−0.0740 (2)	0.7228 (2)	0.0676 (6)
H8A	−0.2671	−0.0597	0.7541	0.081*
H8B	−0.2244	−0.1242	0.6569	0.081*
C9	−0.15798 (18)	0.0611 (2)	0.6958 (2)	0.0654 (6)
H9A	−0.2159	0.1108	0.6499	0.078*
H9B	−0.1351	0.1124	0.7610	0.078*
C10	−0.07539 (13)	0.28694 (17)	0.54277 (14)	0.0397 (4)
C11	−0.08585 (15)	0.41631 (18)	0.57810 (15)	0.0462 (4)
H11	−0.0486	0.4434	0.6451	0.055*
C12	−0.15261 (15)	0.50503 (18)	0.51218 (16)	0.0491 (4)
H12	−0.1592	0.5927	0.5354	0.059*
C13	−0.20962 (14)	0.46749 (17)	0.41312 (15)	0.0437 (4)
C14	−0.28241 (19)	0.5655 (2)	0.34252 (19)	0.0665 (6)
H14A	−0.2651	0.5636	0.2719	0.100*
H14B	−0.2702	0.6543	0.3717	0.100*
H14C	−0.3583	0.5411	0.3389	0.100*
C15	−0.19811 (16)	0.33719 (18)	0.37970 (15)	0.0505 (5)
H15	−0.2365	0.3099	0.3132	0.061*
C16	−0.13115 (16)	0.24717 (18)	0.44277 (15)	0.0490 (5)
H16	−0.1233	0.1602	0.4186	0.059*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
S1	0.0424 (3)	0.0496 (3)	0.0495 (3)	0.00838 (19)	−0.0009 (2)	0.0022 (2)
O1	0.0771 (11)	0.0969 (13)	0.0694 (11)	0.0077 (10)	−0.0045 (9)	0.0205 (10)
O2	0.1130 (14)	0.0765 (11)	0.0788 (12)	0.0330 (10)	0.0134 (11)	−0.0013 (10)
O3	0.0695 (9)	0.0724 (10)	0.0540 (9)	0.0114 (8)	−0.0171 (7)	−0.0045 (8)
O4	0.0426 (7)	0.0613 (8)	0.0773 (10)	0.0105 (6)	0.0124 (7)	0.0019 (7)
N1	0.0576 (10)	0.0477 (9)	0.0524 (10)	0.0109 (7)	0.0135 (8)	0.0075 (8)
C1	0.0721 (16)	0.0828 (18)	0.100 (2)	0.0123 (14)	0.0206 (15)	0.0238 (16)
C2	0.0544 (11)	0.0642 (13)	0.0483 (11)	−0.0089 (10)	0.0031 (9)	0.0088 (10)
C3	0.0907 (18)	0.0882 (17)	0.0389 (11)	−0.0001 (14)	0.0124 (11)	−0.0021 (12)
C4	0.0749 (14)	0.0733 (14)	0.0537 (13)	0.0090 (12)	0.0244 (11)	0.0001 (11)
C5	0.0477 (10)	0.0564 (11)	0.0514 (11)	−0.0090 (8)	0.0115 (9)	0.0062 (9)
C6	0.0674 (13)	0.0554 (12)	0.0416 (11)	−0.0091 (10)	0.0037 (9)	−0.0052 (9)
C7	0.0590 (12)	0.0484 (11)	0.0537 (12)	−0.0069 (9)	0.0100 (9)	−0.0037 (9)
C8	0.0518 (12)	0.0843 (16)	0.0671 (14)	0.0040 (11)	0.0118 (10)	0.0182 (12)
C9	0.0657 (13)	0.0674 (14)	0.0676 (14)	0.0216 (11)	0.0244 (11)	0.0168 (11)
C10	0.0367 (8)	0.0398 (9)	0.0414 (9)	0.0008 (7)	0.0039 (7)	0.0008 (7)
C11	0.0465 (10)	0.0457 (10)	0.0441 (10)	−0.0004 (8)	0.0020 (8)	−0.0077 (8)
C12	0.0532 (10)	0.0364 (9)	0.0562 (12)	0.0027 (8)	0.0059 (9)	−0.0071 (8)
C13	0.0414 (9)	0.0421 (9)	0.0475 (10)	0.0016 (7)	0.0079 (8)	0.0052 (8)
C14	0.0713 (14)	0.0559 (12)	0.0669 (14)	0.0134 (10)	−0.0019 (11)	0.0107 (11)
C15	0.0574 (11)	0.0472 (10)	0.0417 (10)	0.0022 (8)	−0.0043 (8)	−0.0042 (8)
C16	0.0574 (11)	0.0382 (9)	0.0476 (11)	0.0040 (8)	−0.0005 (9)	−0.0057 (8)

Geometric parameters (Å, º)

S1—O3	1.4259 (15)	C6—C7	1.356 (3)
S1—O4	1.4383 (14)	C8—H8A	0.9700
S1—N1	1.6092 (18)	C8—H8B	0.9700
S1—C10	1.7584 (17)	C8—C9	1.513 (3)
O1—C1	1.421 (3)	C9—H9A	0.9700
O1—C2	1.375 (3)	C9—H9B	0.9700
O2—C1	1.400 (3)	C10—C11	1.378 (2)
O2—C7	1.371 (3)	C10—C16	1.386 (2)
N1—H1	0.84 (2)	C11—H11	0.9300
N1—C9	1.467 (3)	C11—C12	1.380 (3)
C1—H1A	0.9700	C12—H12	0.9300
C1—H1B	0.9700	C12—C13	1.375 (3)
C2—C3	1.355 (3)	C13—C14	1.505 (3)
C2—C7	1.367 (3)	C13—C15	1.381 (3)
C3—H3	0.9300	C14—H14A	0.9600
C3—C4	1.388 (3)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C4—C5	1.377 (3)	C15—H15	0.9300
C5—C6	1.390 (3)	C15—C16	1.372 (3)
C5—C8	1.507 (3)	C16—H16	0.9300
C6—H6	0.9300
O3—S1—O4	118.88 (9)	C5—C8—H8B	108.7
O3—S1—N1	108.32 (10)	C5—C8—C9	114.39 (18)
O3—S1—C10	107.96 (9)	H8A—C8—H8B	107.6
O4—S1—N1	105.37 (9)	C9—C8—H8A	108.7
O4—S1—C10	108.07 (9)	C9—C8—H8B	108.7
N1—S1—C10	107.79 (8)	N1—C9—C8	110.25 (17)
C2—O1—C1	105.37 (18)	N1—C9—H9A	109.6
C7—O2—C1	105.8 (2)	N1—C9—H9B	109.6
S1—N1—H1	109.7 (15)	C8—C9—H9A	109.6
C9—N1—S1	119.55 (15)	C8—C9—H9B	109.6
C9—N1—H1	114.4 (15)	H9A—C9—H9B	108.1
O1—C1—H1A	109.8	C11—C10—S1	120.52 (13)
O1—C1—H1B	109.8	C11—C10—C16	120.34 (16)
O2—C1—O1	109.2 (2)	C16—C10—S1	119.13 (13)
O2—C1—H1A	109.8	C10—C11—H11	120.6
O2—C1—H1B	109.8	C10—C11—C12	118.82 (17)
H1A—C1—H1B	108.3	C12—C11—H11	120.6
C3—C2—O1	129.2 (2)	C11—C12—H12	119.1
C3—C2—C7	121.3 (2)	C13—C12—C11	121.88 (17)
C7—C2—O1	109.5 (2)	C13—C12—H12	119.1
C2—C3—H3	121.5	C12—C13—C14	121.13 (17)
C2—C3—C4	116.9 (2)	C12—C13—C15	118.21 (16)
C4—C3—H3	121.5	C15—C13—C14	120.67 (18)
C3—C4—H4	118.7	C13—C14—H14A	109.5
C5—C4—C3	122.5 (2)	C13—C14—H14B	109.5
C5—C4—H4	118.7	C13—C14—H14C	109.5
C4—C5—C6	118.8 (2)	H14A—C14—H14B	109.5
C4—C5—C8	120.9 (2)	H14A—C14—H14C	109.5
C6—C5—C8	120.3 (2)	H14B—C14—H14C	109.5
C5—C6—H6	120.9	C13—C15—H15	119.4
C7—C6—C5	118.18 (19)	C16—C15—C13	121.29 (17)
C7—C6—H6	120.9	C16—C15—H15	119.4
C2—C7—O2	110.14 (19)	C10—C16—H16	120.3
C6—C7—O2	127.6 (2)	C15—C16—C10	119.46 (16)
C6—C7—C2	122.2 (2)	C15—C16—H16	120.3
C5—C8—H8A	108.7
S1—N1—C9—C8	−169.30 (16)	C3—C2—C7—C6	0.5 (3)
S1—C10—C11—C12	178.98 (14)	C3—C4—C5—C6	−0.9 (3)
S1—C10—C16—C15	−179.88 (15)	C3—C4—C5—C8	179.5 (2)
O1—C2—C3—C4	−179.9 (2)	C4—C5—C6—C7	0.9 (3)
O1—C2—C7—O2	−0.2 (2)	C4—C5—C8—C9	79.5 (3)
O1—C2—C7—C6	−179.87 (19)	C5—C6—C7—O2	179.6 (2)
O3—S1—N1—C9	55.48 (18)	C5—C6—C7—C2	−0.8 (3)
O3—S1—C10—C11	6.21 (18)	C5—C8—C9—N1	62.4 (3)
O3—S1—C10—C16	−174.78 (15)	C6—C5—C8—C9	−100.1 (2)
O4—S1—N1—C9	−176.30 (16)	C7—O2—C1—O1	1.0 (3)
O4—S1—C10—C11	−123.57 (16)	C7—C2—C3—C4	−0.4 (3)
O4—S1—C10—C16	55.44 (17)	C8—C5—C6—C7	−179.48 (18)
N1—S1—C10—C11	123.02 (16)	C10—S1—N1—C9	−61.09 (18)
N1—S1—C10—C16	−57.97 (17)	C10—C11—C12—C13	0.7 (3)
C1—O1—C2—C3	−179.6 (2)	C11—C10—C16—C15	−0.9 (3)
C1—O1—C2—C7	0.8 (2)	C11—C12—C13—C14	179.75 (19)
C1—O2—C7—C2	−0.5 (3)	C11—C12—C13—C15	−0.5 (3)
C1—O2—C7—C6	179.1 (2)	C12—C13—C15—C16	−0.5 (3)
C2—O1—C1—O2	−1.1 (3)	C13—C15—C16—C10	1.1 (3)
C2—C3—C4—C5	0.6 (4)	C14—C13—C15—C16	179.33 (19)
C3—C2—C7—O2	−179.8 (2)	C16—C10—C11—C12	0.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.84 (2)	2.19 (2)	3.026 (2)	172 (2)

Symmetry code: (i) −x, −y, −z+1.