N-(3-Meth-oxy-benzo-yl)-4-methyl-benzene-sulfonamide.

In the title compound, C15H15NO4S, the dihedral angle between the benzene rings is 88.87 (1)°. In the crystal, adjacent mol-ecules form inversion dimers through pairs of strong N-H⋯O hydrogen bonds, generating R 2 (2)(8) loops. Two C-H⋯π inter-actions and an aromatic π-π inter-action [centroid-centroid separation = 3.8191 (1) Å] are also observed.

Related literature

For a similar structure, see: Suchetan et al. (2010 ▶).

Experimental

Crystal data

C15H15NO4S

M = 305.34

Triclinic,

a = 9.2474 (7) Å

b = 9.6660 (6) Å

c = 9.8764 (8) Å

α = 70.268 (6)°

β = 64.052 (8)°

γ = 86.231 (5)°

V = 743.69 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.35 × 0.28 × 0.22 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.925, T max = 0.950

11424 measured reflections

2610 independent reflections

2212 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.06

2610 reflections

196 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: n class="Gene">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, global. DOI: 10.1107/S1600536813019107/bg2511sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019107/bg2511Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019107/bg2511Isup3.cml

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

C15H15NO4S	F(000) = 320
Mr = 305.34	Prism
Triclinic, P1	Dx = 1.364 Mg m−3
Hall symbol: -P 1	Melting point: 405 K
a = 9.2474 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6660 (6) Å	Cell parameters from 1123 reflections
c = 9.8764 (8) Å	θ = 2.4–25.0°
α = 70.268 (6)°	µ = 0.23 mm−1
β = 64.052 (8)°	T = 293 K
γ = 86.231 (5)°	Prism, colourless
V = 743.69 (11) Å3	0.35 × 0.28 × 0.22 mm
Z = 2

Bruker APEXII diffractometer	2212 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 25.0°, θmin = 2.4°
phi and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.925, Tmax = 0.950	l = −11→11
11424 measured reflections	3 standard reflections every 1 reflections
2610 independent reflections	intensity decay: 10%

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.194P] where P = (Fo2 + 2Fc2)/3
2610 reflections	(Δ/σ)max = 0.046
196 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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	0.159 (2)	0.588 (2)	0.975 (3)	0.051 (6)*
C1	0.1161 (2)	0.8457 (2)	0.6955 (2)	0.0476 (5)
C2	−0.0258 (2)	0.8795 (3)	0.8029 (2)	0.0613 (6)
H2	−0.0909	0.8073	0.8997	0.074*
C3	−0.0693 (3)	1.0213 (3)	0.7648 (3)	0.0662 (6)
H3	−0.1646	1.0442	0.8371	0.079*
C4	0.0256 (2)	1.1310 (2)	0.6209 (3)	0.0564 (5)
C5	0.1653 (2)	1.0931 (2)	0.5154 (2)	0.0553 (5)
H5	0.2292	1.1646	0.4174	0.066*
C6	0.2129 (2)	0.9520 (2)	0.5511 (2)	0.0518 (5)
H6	0.3084	0.9291	0.4791	0.062*
C7	−0.0228 (3)	1.2854 (3)	0.5835 (3)	0.0798 (7)
H7A	−0.1380	1.2822	0.6220	0.120*
H7B	0.0286	1.3360	0.4696	0.120*
H7C	0.0098	1.3368	0.6350	0.120*
C8	0.3499 (2)	0.7247 (2)	0.8738 (2)	0.0482 (5)
C9	0.3856 (2)	0.6830 (2)	1.0147 (2)	0.0446 (4)
C10	0.3358 (2)	0.5448 (2)	1.1356 (2)	0.0513 (5)
H10	0.2709	0.4755	1.1353	0.062*
C11	0.3844 (2)	0.5127 (2)	1.2554 (2)	0.0554 (5)
H11	0.3525	0.4203	1.3357	0.066*
C12	0.4792 (2)	0.6145 (2)	1.2591 (2)	0.0519 (5)
H12	0.5105	0.5910	1.3411	0.062*
C13	0.5272 (2)	0.7517 (2)	1.1398 (2)	0.0508 (5)
C14	0.4814 (2)	0.7857 (2)	1.0170 (2)	0.0512 (5)
H14	0.5150	0.8777	0.9361	0.061*
C15	0.6780 (3)	0.8309 (3)	1.2494 (3)	0.0782 (7)
H15A	0.5879	0.8074	1.3536	0.117*
H15B	0.7428	0.9162	1.2284	0.117*
H15C	0.7421	0.7488	1.2462	0.117*
N1	0.2204 (2)	0.6435 (2)	0.8917 (2)	0.0519 (4)
O1	0.03105 (19)	0.56323 (17)	0.81816 (17)	0.0674 (4)
O2	0.30852 (18)	0.65075 (17)	0.60995 (16)	0.0643 (4)
O3	0.42784 (17)	0.82263 (17)	0.74840 (17)	0.0633 (4)
O4	0.6206 (2)	0.86118 (18)	1.13085 (19)	0.0731 (5)
S1	0.17181 (6)	0.66553 (6)	0.74433 (6)	0.05142 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0453 (10)	0.0573 (12)	0.0412 (10)	0.0008 (8)	−0.0216 (8)	−0.0141 (9)
C2	0.0511 (12)	0.0712 (15)	0.0451 (11)	−0.0006 (10)	−0.0140 (9)	−0.0093 (10)
C3	0.0524 (12)	0.0811 (17)	0.0590 (13)	0.0133 (11)	−0.0192 (11)	−0.0256 (12)
C4	0.0553 (12)	0.0622 (13)	0.0619 (13)	0.0095 (10)	−0.0341 (11)	−0.0227 (11)
C5	0.0562 (12)	0.0537 (12)	0.0494 (11)	−0.0019 (9)	−0.0231 (10)	−0.0091 (9)
C6	0.0478 (11)	0.0584 (12)	0.0427 (10)	0.0014 (9)	−0.0168 (9)	−0.0134 (9)
C7	0.0820 (17)	0.0748 (17)	0.0900 (18)	0.0235 (14)	−0.0445 (15)	−0.0313 (14)
C8	0.0462 (10)	0.0508 (11)	0.0453 (11)	0.0046 (9)	−0.0213 (9)	−0.0124 (9)
C9	0.0416 (10)	0.0490 (11)	0.0425 (10)	0.0064 (8)	−0.0192 (8)	−0.0144 (8)
C10	0.0537 (11)	0.0480 (11)	0.0516 (11)	0.0014 (9)	−0.0252 (9)	−0.0133 (9)
C11	0.0625 (13)	0.0487 (12)	0.0494 (11)	0.0032 (9)	−0.0274 (10)	−0.0064 (9)
C12	0.0522 (11)	0.0606 (13)	0.0453 (11)	0.0097 (9)	−0.0257 (9)	−0.0163 (9)
C13	0.0486 (11)	0.0543 (12)	0.0526 (11)	0.0042 (9)	−0.0259 (9)	−0.0171 (9)
C14	0.0518 (11)	0.0492 (11)	0.0501 (11)	0.0008 (9)	−0.0254 (9)	−0.0094 (9)
C15	0.0851 (17)	0.0866 (18)	0.0832 (17)	−0.0041 (14)	−0.0573 (15)	−0.0237 (14)
N1	0.0531 (10)	0.0574 (11)	0.0395 (9)	−0.0067 (8)	−0.0228 (8)	−0.0048 (8)
O1	0.0801 (10)	0.0657 (10)	0.0571 (9)	−0.0210 (8)	−0.0398 (8)	−0.0038 (7)
O2	0.0778 (10)	0.0666 (10)	0.0472 (8)	0.0167 (8)	−0.0259 (7)	−0.0220 (7)
O3	0.0605 (9)	0.0685 (10)	0.0493 (8)	−0.0100 (7)	−0.0258 (7)	−0.0015 (7)
O4	0.0847 (11)	0.0708 (11)	0.0749 (10)	−0.0137 (8)	−0.0520 (9)	−0.0113 (8)
S1	0.0595 (3)	0.0537 (3)	0.0418 (3)	−0.0022 (2)	−0.0265 (2)	−0.0105 (2)

C1—C6	1.381 (3)	C9—C10	1.394 (3)
C1—C2	1.383 (3)	C10—C11	1.378 (3)
C1—S1	1.750 (2)	C10—H10	0.9300
C2—C3	1.377 (3)	C11—C12	1.380 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.389 (3)	C12—C13	1.381 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.380 (3)	C13—O4	1.366 (2)
C4—C7	1.500 (3)	C13—C14	1.385 (3)
C5—C6	1.383 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—O4	1.426 (3)
C6—H6	0.9300	C15—H15A	0.9600
C7—H7A	0.9600	C15—H15B	0.9600
C7—H7B	0.9600	C15—H15C	0.9600
C7—H7C	0.9600	N1—S1	1.6477 (16)
C8—O3	1.211 (2)	N1—HN1	0.79 (2)
C8—N1	1.388 (2)	O1—S1	1.4338 (15)
C8—C9	1.488 (3)	O2—S1	1.4199 (15)
C9—C14	1.386 (3)
C6—C1—C2	120.7 (2)	C11—C10—H10	120.5
C6—C1—S1	120.07 (15)	C9—C10—H10	120.5
C2—C1—S1	119.19 (15)	C10—C11—C12	121.46 (19)
C3—C2—C1	119.2 (2)	C10—C11—H11	119.3
C3—C2—H2	120.4	C12—C11—H11	119.3
C1—C2—H2	120.4	C11—C12—C13	119.41 (18)
C2—C3—C4	121.5 (2)	C11—C12—H12	120.3
C2—C3—H3	119.3	C13—C12—H12	120.3
C4—C3—H3	119.3	O4—C13—C12	124.67 (18)
C5—C4—C3	117.8 (2)	O4—C13—C14	115.23 (18)
C5—C4—C7	121.7 (2)	C12—C13—C14	120.10 (18)
C3—C4—C7	120.5 (2)	C13—C14—C9	120.09 (18)
C4—C5—C6	121.92 (19)	C13—C14—H14	120.0
C4—C5—H5	119.0	C9—C14—H14	120.0
C6—C5—H5	119.0	O4—C15—H15A	109.5
C1—C6—C5	118.76 (19)	O4—C15—H15B	109.5
C1—C6—H6	120.6	H15A—C15—H15B	109.5
C5—C6—H6	120.6	O4—C15—H15C	109.5
C4—C7—H7A	109.5	H15A—C15—H15C	109.5
C4—C7—H7B	109.5	H15B—C15—H15C	109.5
H7A—C7—H7B	109.5	C8—N1—S1	123.04 (14)
C4—C7—H7C	109.5	C8—N1—HN1	122.9 (15)
H7A—C7—H7C	109.5	S1—N1—HN1	113.9 (15)
H7B—C7—H7C	109.5	C13—O4—C15	118.08 (17)
O3—C8—N1	120.27 (18)	O2—S1—O1	118.61 (10)
O3—C8—C9	123.41 (17)	O2—S1—N1	109.61 (9)
N1—C8—C9	116.31 (16)	O1—S1—N1	103.41 (9)
C14—C9—C10	120.02 (17)	O2—S1—C1	109.64 (9)
C14—C9—C8	116.76 (17)	O1—S1—C1	109.03 (9)
C10—C9—C8	123.10 (17)	N1—S1—C1	105.68 (9)
C11—C10—C9	118.92 (18)
C6—C1—C2—C3	−0.4 (3)	C11—C12—C13—C14	−0.6 (3)
S1—C1—C2—C3	179.73 (17)	O4—C13—C14—C9	−179.59 (17)
C1—C2—C3—C4	0.2 (3)	C12—C13—C14—C9	0.8 (3)
C2—C3—C4—C5	0.7 (3)	C10—C9—C14—C13	−0.3 (3)
C2—C3—C4—C7	−178.8 (2)	C8—C9—C14—C13	−176.47 (17)
C3—C4—C5—C6	−1.4 (3)	O3—C8—N1—S1	4.2 (3)
C7—C4—C5—C6	178.2 (2)	C9—C8—N1—S1	−175.21 (13)
C2—C1—C6—C5	−0.2 (3)	C12—C13—O4—C15	2.4 (3)
S1—C1—C6—C5	179.63 (14)	C14—C13—O4—C15	−177.17 (19)
C4—C5—C6—C1	1.1 (3)	C8—N1—S1—O2	54.03 (19)
O3—C8—C9—C14	18.3 (3)	C8—N1—S1—O1	−178.56 (16)
N1—C8—C9—C14	−162.34 (17)	C8—N1—S1—C1	−64.03 (18)
O3—C8—C9—C10	−157.8 (2)	C6—C1—S1—O2	−7.39 (19)
N1—C8—C9—C10	21.6 (3)	C2—C1—S1—O2	172.45 (15)
C14—C9—C10—C11	−0.5 (3)	C6—C1—S1—O1	−138.75 (16)
C8—C9—C10—C11	175.44 (17)	C2—C1—S1—O1	41.08 (18)
C9—C10—C11—C12	0.7 (3)	C6—C1—S1—N1	110.66 (17)
C10—C11—C12—C13	−0.2 (3)	C2—C1—S1—N1	−69.50 (17)
C11—C12—C13—O4	179.91 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1i	0.79 (2)	2.14 (2)	2.920 (2)	170 (2)
C15—H15B···Cg1ii	0.96	2.77	3.576 (3)	141
C7—H7A···Cg2iii	0.96	2.94	3.753 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the sulfonyl-bound and carbonyl-bound benzene rings respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O1i	0.79 (2)	2.14 (2)	2.920 (2)	170 (2)
C15—H15B⋯Cg1ii	0.96	2.77	3.576 (3)	141
C7—H7A⋯Cg2iii	0.96	2.94	3.753 (3)	143

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