N-(3-Meth-oxy-benzo-yl)-2-methyl-benzene-sulfonamide.

In the title compound, C15H15NO4S, the dihedral angle between the methyl- and meth-oxy-substituted benzene rings is 88.99 (12)°. An intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, adjacent mol-ecules form inversion-related dimers through strong N-H⋯O hydrogen bonds, generating R 2 (2)(8) loops. The dimers are further connected through C-H⋯O inter-actions that form C(8) chains parallel to (001). Mol-ecules are also connected through other C-H⋯O hydrogen bonds along the b axis, forming additional C(8) chains. Two aromatic π-π stacking inter-actions [centroid-centroid separations = 3.6150 (1) and 3.6837 (1) Å] generate a three-dimensional architecture.

Related literature

For similar structures, see: Gowda et al. (2010 ▶); Suchetan et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C15H15NO4S

M = 305.34

Monoclinic,

a = 26.713 (5) Å

b = 7.3717 (4) Å

c = 19.636 (3) Å

β = 131.21 (3)°

V = 2908.7 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.33 × 0.27 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

5294 measured reflections

2558 independent reflections

1970 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.118

S = 1.04

2558 reflections

196 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813018539/sj5340sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018539/sj5340Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018539/sj5340Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H15NO4S	Prism
Mr = 305.34	Dx = 1.394 Mg m−3
Monoclinic, C2/c	Melting point: 423 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 26.713 (5) Å	Cell parameters from 1232 reflections
b = 7.3717 (4) Å	θ = 2.8–25.0°
c = 19.636 (3) Å	µ = 0.24 mm−1
β = 131.21 (3)°	T = 293 K
V = 2908.7 (7) Å3	Prism, colourless
Z = 8	0.33 × 0.27 × 0.22 mm
F(000) = 1280

Bruker APEXII CCD area-detector diffractometer	1970 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 25.0°, θmin = 2.8°
φ and ω scans	h = −31→31
5294 measured reflections	k = −8→8
2558 independent reflections	l = −14→23

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.0171P] where P = (Fo2 + 2Fc2)/3
2558 reflections	(Δ/σ)max = 0.001
196 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.35 e Å−3
0 constraints

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
HN1	0.0737 (12)	0.796 (3)	0.2976 (17)	0.055 (8)*
C1	0.05769 (11)	0.6312 (3)	0.13024 (14)	0.0444 (5)
C9	0.18751 (12)	0.9525 (3)	0.40254 (15)	0.0425 (5)
C10	0.16739 (12)	0.9650 (3)	0.45194 (16)	0.0479 (6)
H10	0.1231	0.9451	0.4237	0.057*
C8	0.14165 (12)	0.9088 (3)	0.30428 (16)	0.0467 (6)
C2	0.06638 (11)	0.4482 (3)	0.15570 (16)	0.0488 (6)
C6	0.07526 (12)	0.6977 (3)	0.08233 (16)	0.0546 (6)
H6	0.0689	0.8195	0.0662	0.066*
C14	0.25399 (13)	0.9826 (3)	0.44521 (17)	0.0529 (6)
H14	0.2678	0.9748	0.4125	0.063*
C11	0.21314 (12)	1.0071 (3)	0.54308 (17)	0.0496 (6)
C13	0.29856 (13)	1.0235 (3)	0.53520 (18)	0.0602 (7)
H13	0.3429	1.0430	0.5635	0.072*
C12	0.27921 (12)	1.0365 (3)	0.58542 (17)	0.0529 (6)
H12	0.3102	1.0646	0.6468	0.063*
C5	0.10253 (13)	0.5803 (4)	0.05870 (18)	0.0653 (7)
H5	0.1146	0.6233	0.0267	0.078*
C4	0.11146 (14)	0.4011 (4)	0.08281 (18)	0.0666 (8)
H4	0.1296	0.3227	0.0670	0.080*
C3	0.09384 (13)	0.3358 (3)	0.13017 (18)	0.0601 (7)
H3	0.1004	0.2136	0.1457	0.072*
C7	0.04728 (14)	0.3666 (3)	0.20628 (19)	0.0651 (7)
H7A	0.0607	0.4466	0.2543	0.098*
H7B	0.0691	0.2516	0.2312	0.098*
H7C	−0.0001	0.3496	0.1655	0.098*
C15	0.23539 (16)	1.0486 (5)	0.68140 (19)	0.0927 (11)
H15A	0.2674	0.9521	0.7117	0.139*
H15B	0.2121	1.0546	0.7032	0.139*
H15C	0.2578	1.1616	0.6934	0.139*
O1	0.00755 (9)	0.9515 (2)	0.10733 (11)	0.0614 (5)
O2	−0.02956 (7)	0.7037 (2)	0.14851 (11)	0.0527 (4)
O3	0.15524 (9)	0.9414 (2)	0.25752 (12)	0.0646 (5)
O4	0.18890 (10)	1.0151 (3)	0.58597 (13)	0.0771 (6)
S1	0.02251 (3)	0.78797 (8)	0.15606 (4)	0.0461 (2)
N1	0.08109 (10)	0.8300 (3)	0.26647 (13)	0.0456 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0325 (12)	0.0577 (14)	0.0369 (12)	−0.0007 (11)	0.0202 (11)	−0.0079 (10)
C9	0.0428 (13)	0.0396 (11)	0.0460 (14)	−0.0036 (10)	0.0296 (12)	−0.0046 (10)
C10	0.0408 (14)	0.0560 (13)	0.0514 (15)	−0.0117 (11)	0.0323 (13)	−0.0128 (11)
C8	0.0477 (15)	0.0498 (13)	0.0500 (15)	−0.0079 (11)	0.0354 (14)	−0.0059 (11)
C2	0.0370 (13)	0.0540 (13)	0.0470 (14)	−0.0035 (11)	0.0240 (13)	−0.0114 (11)
C6	0.0477 (15)	0.0703 (16)	0.0468 (15)	0.0002 (12)	0.0315 (14)	−0.0041 (12)
C14	0.0455 (15)	0.0674 (15)	0.0538 (16)	−0.0046 (12)	0.0361 (14)	−0.0031 (12)
C11	0.0479 (15)	0.0570 (13)	0.0509 (15)	−0.0084 (12)	0.0355 (14)	−0.0110 (11)
C13	0.0386 (14)	0.0809 (17)	0.0573 (17)	−0.0073 (13)	0.0299 (14)	−0.0053 (13)
C12	0.0424 (15)	0.0643 (15)	0.0435 (15)	−0.0053 (12)	0.0247 (13)	−0.0060 (11)
C5	0.0528 (17)	0.100 (2)	0.0516 (16)	−0.0027 (16)	0.0381 (15)	−0.0121 (15)
C4	0.0513 (17)	0.087 (2)	0.0610 (18)	0.0025 (15)	0.0369 (16)	−0.0217 (15)
C3	0.0491 (16)	0.0606 (15)	0.0614 (17)	0.0022 (13)	0.0324 (15)	−0.0135 (13)
C7	0.0658 (19)	0.0565 (15)	0.075 (2)	−0.0007 (13)	0.0473 (18)	0.0007 (13)
C15	0.071 (2)	0.164 (3)	0.0525 (19)	−0.016 (2)	0.0442 (19)	−0.0258 (19)
O1	0.0668 (12)	0.0571 (9)	0.0569 (12)	0.0121 (9)	0.0393 (11)	0.0084 (8)
O2	0.0360 (9)	0.0696 (10)	0.0542 (10)	−0.0035 (8)	0.0305 (9)	−0.0118 (8)
O3	0.0606 (12)	0.0922 (13)	0.0561 (12)	−0.0179 (10)	0.0449 (11)	−0.0102 (9)
O4	0.0531 (12)	0.1345 (16)	0.0517 (12)	−0.0218 (11)	0.0380 (11)	−0.0281 (11)
S1	0.0400 (4)	0.0541 (4)	0.0427 (4)	0.0021 (3)	0.0267 (3)	−0.0040 (3)
N1	0.0450 (12)	0.0577 (12)	0.0394 (12)	−0.0091 (9)	0.0301 (11)	−0.0074 (9)

C1—C6	1.388 (3)	C13—H13	0.9300
C1—C2	1.404 (3)	C12—H12	0.9300
C1—S1	1.762 (2)	C5—C4	1.370 (4)
C9—C10	1.388 (3)	C5—H5	0.9300
C9—C14	1.394 (3)	C4—C3	1.376 (4)
C9—C8	1.487 (3)	C4—H4	0.9300
C10—C11	1.382 (3)	C3—H3	0.9300
C10—H10	0.9300	C7—H7A	0.9600
C8—O3	1.213 (3)	C7—H7B	0.9600
C8—N1	1.387 (3)	C7—H7C	0.9600
C2—C3	1.400 (3)	C15—O4	1.431 (3)
C2—C7	1.509 (3)	C15—H15A	0.9600
C6—C5	1.393 (3)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C14—C13	1.363 (3)	O1—S1	1.4232 (16)
C14—H14	0.9300	O2—S1	1.4391 (16)
C11—O4	1.360 (3)	S1—N1	1.666 (2)
C11—C12	1.385 (3)	N1—HN1	0.79 (2)
C13—C12	1.386 (3)
C6—C1—C2	122.0 (2)	C4—C5—H5	120.2
C6—C1—S1	116.49 (18)	C6—C5—H5	120.2
C2—C1—S1	121.48 (17)	C5—C4—C3	120.7 (2)
C10—C9—C14	119.7 (2)	C5—C4—H4	119.6
C10—C9—C8	123.6 (2)	C3—C4—H4	119.6
C14—C9—C8	116.6 (2)	C4—C3—C2	121.9 (2)
C11—C10—C9	120.0 (2)	C4—C3—H3	119.1
C11—C10—H10	120.0	C2—C3—H3	119.1
C9—C10—H10	120.0	C2—C7—H7A	109.5
O3—C8—N1	120.2 (2)	C2—C7—H7B	109.5
O3—C8—C9	122.5 (2)	H7A—C7—H7B	109.5
N1—C8—C9	117.3 (2)	C2—C7—H7C	109.5
C3—C2—C1	116.3 (2)	H7A—C7—H7C	109.5
C3—C2—C7	119.0 (2)	H7B—C7—H7C	109.5
C1—C2—C7	124.7 (2)	O4—C15—H15A	109.5
C1—C6—C5	119.4 (2)	O4—C15—H15B	109.5
C1—C6—H6	120.3	H15A—C15—H15B	109.5
C5—C6—H6	120.3	O4—C15—H15C	109.5
C13—C14—C9	119.5 (2)	H15A—C15—H15C	109.5
C13—C14—H14	120.2	H15B—C15—H15C	109.5
C9—C14—H14	120.2	C11—O4—C15	117.5 (2)
O4—C11—C10	115.8 (2)	O1—S1—O2	118.18 (11)
O4—C11—C12	124.0 (2)	O1—S1—N1	108.93 (10)
C10—C11—C12	120.2 (2)	O2—S1—N1	103.29 (10)
C14—C13—C12	121.4 (2)	O1—S1—C1	109.21 (11)
C14—C13—H13	119.3	O2—S1—C1	110.47 (10)
C12—C13—H13	119.3	N1—S1—C1	105.95 (11)
C11—C12—C13	119.1 (2)	C8—N1—S1	122.61 (17)
C11—C12—H12	120.4	C8—N1—HN1	120.7 (19)
C13—C12—H12	120.4	S1—N1—HN1	116.5 (19)
C4—C5—C6	119.6 (2)
C14—C9—C10—C11	0.0 (3)	C5—C4—C3—C2	−0.1 (4)
C8—C9—C10—C11	−179.7 (2)	C1—C2—C3—C4	0.1 (4)
C10—C9—C8—O3	161.3 (2)	C7—C2—C3—C4	179.1 (2)
C14—C9—C8—O3	−18.4 (3)	C10—C11—O4—C15	176.7 (2)
C10—C9—C8—N1	−17.9 (3)	C12—C11—O4—C15	−2.7 (4)
C14—C9—C8—N1	162.4 (2)	O2—O2—S1—O1	0.00 (5)
C6—C1—C2—C3	0.0 (3)	O2—O2—S1—N1	0.00 (6)
S1—C1—C2—C3	178.99 (18)	O2—O2—S1—C1	0.00 (4)
C6—C1—C2—C7	−178.9 (2)	C6—C1—S1—O1	10.5 (2)
S1—C1—C2—C7	0.1 (3)	C2—C1—S1—O1	−168.48 (18)
C2—C1—C6—C5	−0.2 (4)	C6—C1—S1—O2	142.13 (18)
S1—C1—C6—C5	−179.17 (18)	C2—C1—S1—O2	−36.9 (2)
C10—C9—C14—C13	0.2 (3)	C6—C1—S1—O2	142.13 (18)
C8—C9—C14—C13	179.9 (2)	C2—C1—S1—O2	−36.9 (2)
C9—C10—C11—O4	−179.6 (2)	C6—C1—S1—N1	−106.65 (19)
C9—C10—C11—C12	−0.1 (3)	C2—C1—S1—N1	74.3 (2)
C9—C14—C13—C12	−0.2 (4)	O3—C8—N1—S1	−3.9 (3)
O4—C11—C12—C13	179.5 (2)	C9—C8—N1—S1	175.28 (15)
C10—C11—C12—C13	0.1 (4)	O1—S1—N1—C8	−54.9 (2)
C14—C13—C12—C11	0.1 (4)	O2—S1—N1—C8	178.66 (18)
C1—C6—C5—C4	0.2 (4)	O2—S1—N1—C8	178.66 (18)
C6—C5—C4—C3	0.0 (4)	C1—S1—N1—C8	62.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O2i	0.80 (3)	2.15 (4)	2.929 (4)	166
C3—H3···O3ii	0.93	2.60	3.463 (3)	155
C10—H10···O2i	0.93	2.60	3.404 (3)	145
C15—H15B···O3iii	0.96	2.36	3.323 (3)	178
C6—H6···O1	0.93	2.46	2.861 (4)	106

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O2i	0.80 (3)	2.15 (4)	2.929 (4)	166
C3—H3⋯O3ii	0.93	2.60	3.463 (3)	155
C10—H10⋯O2i	0.93	2.60	3.404 (3)	145
C15—H15B⋯O3iii	0.96	2.36	3.323 (3)	178
C6—H6⋯O1	0.93	2.46	2.861 (4)	106

Symmetry codes: (i) ; (ii) ; (iii) .