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

Huang, K.-B.; Zhang, G.-J.

doi:10.1107/S2056989015010555

organic compounds

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Volume 71| Part 7| July 2015| Page o452

doi:10.1107/S2056989015010555

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

Ke-Bin Huang ^a and Gui-Jie Zhang ^b ^*

^aSchool of Chemistry and Chemical Engineering, Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education), Guangxi Normal University, Guilin 541004, People's Republic of China, and ^bCollege of Pharmacy, Guilin Medical College, Guilin 541004, People's Republic of China
^*Correspondence e-mail: zhangguijie001@126.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 25 May 2015; accepted 1 June 2015; online 6 June 2015)

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 R₂²(8) loops.

Keywords: crystal structure; methylbenzenesulfonamide derivatives; hydrogen bonding.

CCDC reference: 1401539

1. Related literature

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

2. Experimental

2.1. Crystal data

C₁₆H₁₇NO₄S
M_r = 319.37
Monoclinic, P 2₁ /n
a = 12.3265 (2) Å
b = 9.96026 (16) Å
c = 12.7021 (3) Å
β = 100.5980 (18)°
V = 1532.90 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.40 × 0.20 × 0.12 mm

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 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

Table 1
Hydrogen-bond geometry (Å, °)

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.

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.

Supporting information

CCDC reference: 1401539

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015010555/hb7436sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015010555/hb7436Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015010555/hb7436Isup3.cml

checkCIF report

Related literature top

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

Experimental top

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.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of title compound, with atom labelling. Displacement ellipsoids are drawn at 30% probability level.

N-[2-(Benzo[d][1,3]dioxol-5-yl)ethyl]-4-methylbenzenesulfonamide top

Crystal data top

C₁₆H₁₇NO₄S	F(000) = 672
M_r = 319.37	D_x = 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 top

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	R_int = 0.029
Detector resolution: 16.1623 pixels mm^-1	θ_max = 26.4°, θ_min = 2.9°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
T_min = 0.868, T_max = 1.000	l = −15→15
12219 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) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0499P)² + 0.4898P] where P = (F_o² + 2F_c²)/3
3136 reflections	(Δ/σ)_max < 0.001
204 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₆H₁₇NO₄S	V = 1532.90 (5) Å³
M_r = 319.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.3265 (2) Å	µ = 0.23 mm⁻¹
b = 9.96026 (16) Å	T = 293 K
c = 12.7021 (3) Å	0.40 × 0.20 × 0.12 mm
β = 100.5980 (18)°

Data collection top

Agilent SuperNova (single source at offset), Eos diffractometer	3136 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2587 reflections with I > 2σ(I)
T_min = 0.868, T_max = 1.000	R_int = 0.029
12219 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.19 e Å⁻³
3136 reflections	Δρ_min = −0.39 e Å⁻³
204 parameters

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
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 (Å²) top

	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) top

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) top

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.

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

The authors thank the National Natural Science Foundation of China (21401031), the Natural Science Foundation of Guangxi Province (2014GXNSFBA118035) as well as the Key Laboratory Open Fund of the Ministry of Education for financial support (CMEMR2013-A14).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barn, D. R., Caulfield, W. L., Cottney, J., McGurk, K., Morphy, J. R., Rankovic, Z. & Roberts, B. (2001). Bioorg. Med. Chem. 9, 2609–2624. Web of Science CrossRef PubMed CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ghorai, M. K., Kumar, A. & Tiwari, D. P. (2010). J. Org. Chem. 75, 137–151. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Page o452

doi:10.1107/S2056989015010555

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

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