N-(4-Meth-oxy-benzo-yl)benzene-sulfon-amide.

In the title compound, C14H13NO4S, the dihedral angle between the aromatic rings is 69.81 (1)°; the dihedral angle between the planes defined by the S-N-C=O segment of the central chain and the sulfonyl benzene ring is 74.91 (1)°. In the crystal, the mol-ecules are linked by weak N-H⋯O hydrogen bonds into C(4) chains running along [100]. The mol-ecules in adjacent chains are linked by weak C-H⋯O inter-actions, generating R 2 (2) (16) dimeric pairs. Weak C-H⋯π inter-actions connect the double chains into (001) sheets.

Related literature

For similar structures, see: Gowda et al. (2009 ▶); Suchetan et al. (2009 ▶, 2010 ▶); Sreenivasa et al. (2013 ▶).

Experimental

Crystal data

C14H13NO4S

M = 291.31

Triclinic,

a = 5.3059 (5) Å

b = 10.6343 (10) Å

c = 11.9139 (11) Å

α = 89.792 (3)°

β = 87.392 (3)°

γ = 83.944 (3)°

V = 667.79 (11) Å3

Z = 2

Cu Kα radiation

μ = 2.28 mm−1

T = 293 K

0.37 × 0.26 × 0.20 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.515, T max = 0.633

8561 measured reflections

2168 independent reflections

2076 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.158

S = 1.13

2168 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.84 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. DOI: 10.1107/S1600536814001330/hb7187sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001330/hb7187Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001330/hb7187Isup3.cml

CCDC reference:

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

C14H13NO4S	F(000) = 304
Mr = 291.31	Prism
Triclinic, P1	Dx = 1.449 Mg m−3
Hall symbol: -P 1	Melting point: 399 K
a = 5.3059 (5) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.6343 (10) Å	Cell parameters from 25 reflections
c = 11.9139 (11) Å	θ = 3.7–64.8°
α = 89.792 (3)°	µ = 2.28 mm−1
β = 87.392 (3)°	T = 293 K
γ = 83.944 (3)°	Prism, colourless
V = 667.79 (11) Å3	0.37 × 0.26 × 0.20 mm
Z = 2

Bruker APEXII diffractometer	2076 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite monochromator	θmax = 64.8°, θmin = 3.7°
phi and φ scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.515, Tmax = 0.633	l = −13→13
8561 measured reflections	3 standard reflections every 120 min
2168 independent reflections	intensity decay: 1%

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.1013P)2 + 0.1754P] where P = (Fo2 + 2Fc2)/3
2168 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.84 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
O1	0.2427 (3)	0.36646 (17)	0.44504 (16)	0.0596 (5)
N1	0.6766 (4)	0.40318 (19)	0.36803 (17)	0.0478 (5)
O3	0.4534 (3)	0.39943 (16)	0.21164 (15)	0.0559 (5)
O4	1.1816 (4)	0.81223 (19)	0.06023 (17)	0.0695 (6)
C13	0.9563 (4)	0.5966 (2)	0.26610 (18)	0.0421 (5)
H13	0.9898	0.5737	0.3398	0.051*
C7	0.6197 (4)	0.4435 (2)	0.25993 (19)	0.0424 (5)
O2	0.6259 (4)	0.30297 (18)	0.54898 (15)	0.0624 (5)
C9	0.7269 (6)	0.5777 (3)	0.1010 (2)	0.0609 (7)
H9	0.6030	0.5417	0.0631	0.073*
C1	0.5310 (4)	0.1655 (2)	0.37956 (18)	0.0405 (5)
C12	1.0878 (4)	0.6857 (2)	0.2130 (2)	0.0475 (6)
H12	1.2101	0.7227	0.2512	0.057*
C8	0.7732 (4)	0.5405 (2)	0.21008 (18)	0.0402 (5)
C11	1.0410 (5)	0.7213 (2)	0.1032 (2)	0.0472 (6)
C5	0.3772 (5)	0.0164 (2)	0.2584 (2)	0.0564 (6)
H5	0.2579	−0.0048	0.2089	0.068*
C3	0.7531 (5)	−0.0405 (3)	0.3552 (3)	0.0649 (8)
H3	0.8890	−0.0996	0.3709	0.078*
C4	0.5776 (5)	−0.0707 (2)	0.2829 (2)	0.0547 (6)
H4	0.5930	−0.1504	0.2500	0.066*
C2	0.7307 (5)	0.0778 (3)	0.4055 (2)	0.0574 (6)
H2	0.8487	0.0979	0.4562	0.069*
C14	1.1590 (10)	0.8451 (4)	−0.0546 (3)	0.0986 (13)
H14A	1.2092	0.7720	−0.1005	0.148*
H14B	1.2665	0.9100	−0.0734	0.148*
H14C	0.9860	0.8757	−0.0676	0.148*
C6	0.3516 (4)	0.1360 (2)	0.3071 (2)	0.0498 (6)
H6	0.2157	0.1948	0.2910	0.060*
C10	0.8596 (6)	0.6669 (3)	0.0467 (2)	0.0635 (7)
H10	0.8267	0.6899	−0.0270	0.076*
S1	0.50162 (10)	0.31426 (5)	0.44550 (4)	0.0452 (3)
HN1	0.808 (6)	0.419 (4)	0.397 (3)	0.091 (12)*

	U11	U22	U33	U12	U13	U23
O1	0.0540 (10)	0.0592 (10)	0.0642 (11)	−0.0033 (8)	0.0092 (8)	−0.0138 (8)
N1	0.0543 (12)	0.0501 (11)	0.0432 (11)	−0.0222 (9)	−0.0093 (9)	0.0000 (8)
O3	0.0563 (10)	0.0581 (10)	0.0573 (10)	−0.0197 (8)	−0.0149 (8)	−0.0071 (8)
O4	0.0829 (14)	0.0677 (12)	0.0582 (12)	−0.0183 (10)	0.0158 (10)	0.0140 (9)
C13	0.0460 (12)	0.0463 (11)	0.0348 (11)	−0.0079 (9)	−0.0035 (9)	−0.0026 (9)
C7	0.0460 (12)	0.0400 (11)	0.0419 (12)	−0.0065 (9)	−0.0039 (9)	−0.0105 (9)
O2	0.0851 (13)	0.0689 (11)	0.0385 (9)	−0.0294 (10)	−0.0111 (9)	−0.0024 (8)
C9	0.0753 (18)	0.0729 (17)	0.0393 (13)	−0.0241 (13)	−0.0155 (12)	−0.0048 (11)
C1	0.0383 (11)	0.0445 (11)	0.0403 (11)	−0.0142 (8)	0.0036 (8)	−0.0022 (8)
C12	0.0477 (12)	0.0519 (13)	0.0445 (12)	−0.0126 (10)	−0.0019 (9)	−0.0006 (10)
C8	0.0427 (11)	0.0417 (11)	0.0361 (11)	−0.0047 (9)	0.0001 (9)	−0.0081 (8)
C11	0.0523 (13)	0.0460 (12)	0.0418 (12)	−0.0035 (10)	0.0118 (10)	−0.0010 (9)
C5	0.0568 (14)	0.0537 (14)	0.0624 (16)	−0.0215 (11)	−0.0058 (11)	−0.0110 (11)
C3	0.0542 (15)	0.0558 (15)	0.083 (2)	0.0029 (12)	−0.0004 (14)	−0.0073 (13)
C4	0.0572 (14)	0.0445 (12)	0.0628 (16)	−0.0153 (10)	0.0159 (12)	−0.0095 (10)
C2	0.0450 (13)	0.0652 (15)	0.0628 (15)	−0.0071 (11)	−0.0084 (11)	−0.0083 (12)
C14	0.147 (4)	0.091 (2)	0.0561 (19)	−0.018 (2)	0.032 (2)	0.0156 (17)
C6	0.0449 (12)	0.0469 (12)	0.0598 (14)	−0.0128 (9)	−0.0081 (10)	−0.0050 (10)
C10	0.084 (2)	0.0740 (17)	0.0338 (12)	−0.0134 (14)	−0.0043 (12)	0.0032 (11)
S1	0.0516 (4)	0.0468 (4)	0.0393 (4)	−0.0156 (3)	0.0011 (3)	−0.0074 (2)

O1—S1	1.4264 (19)	C1—S1	1.758 (2)
N1—C7	1.392 (3)	C12—C11	1.387 (3)
N1—S1	1.646 (2)	C12—H12	0.9300
N1—HN1	0.82 (3)	C11—C10	1.376 (4)
O3—C7	1.211 (3)	C5—C4	1.376 (4)
O4—C11	1.367 (3)	C5—C6	1.390 (4)
O4—C14	1.418 (4)	C5—H5	0.9300
C13—C12	1.371 (3)	C3—C4	1.360 (4)
C13—C8	1.389 (3)	C3—C2	1.388 (4)
C13—H13	0.9300	C3—H3	0.9300
C7—C8	1.486 (3)	C4—H4	0.9300
O2—S1	1.4232 (19)	C2—H2	0.9300
C9—C10	1.381 (4)	C14—H14A	0.9600
C9—C8	1.382 (3)	C14—H14B	0.9600
C9—H9	0.9300	C14—H14C	0.9600
C1—C6	1.375 (3)	C6—H6	0.9300
C1—C2	1.381 (4)	C10—H10	0.9300
C7—N1—S1	123.91 (17)	C4—C3—C2	120.4 (2)
C7—N1—HN1	122 (3)	C4—C3—H3	119.8
S1—N1—HN1	114 (3)	C2—C3—H3	119.8
C11—O4—C14	118.2 (3)	C3—C4—C5	120.2 (2)
C12—C13—C8	120.1 (2)	C3—C4—H4	119.9
C12—C13—H13	119.9	C5—C4—H4	119.9
C8—C13—H13	119.9	C1—C2—C3	119.2 (2)
O3—C7—N1	120.0 (2)	C1—C2—H2	120.4
O3—C7—C8	123.6 (2)	C3—C2—H2	120.4
N1—C7—C8	116.42 (19)	O4—C14—H14A	109.5
C10—C9—C8	121.9 (2)	O4—C14—H14B	109.5
C10—C9—H9	119.1	H14A—C14—H14B	109.5
C8—C9—H9	119.1	O4—C14—H14C	109.5
C6—C1—C2	121.0 (2)	H14A—C14—H14C	109.5
C6—C1—S1	120.16 (18)	H14B—C14—H14C	109.5
C2—C1—S1	118.81 (18)	C1—C6—C5	118.7 (2)
C13—C12—C11	120.9 (2)	C1—C6—H6	120.6
C13—C12—H12	119.5	C5—C6—H6	120.6
C11—C12—H12	119.5	C11—C10—C9	119.1 (2)
C9—C8—C13	118.3 (2)	C11—C10—H10	120.4
C9—C8—C7	117.3 (2)	C9—C10—H10	120.4
C13—C8—C7	124.4 (2)	O2—S1—O1	119.44 (12)
O4—C11—C10	125.0 (2)	O2—S1—N1	103.74 (11)
O4—C11—C12	115.3 (2)	O1—S1—N1	109.21 (11)
C10—C11—C12	119.6 (2)	O2—S1—C1	108.88 (11)
C4—C5—C6	120.5 (2)	O1—S1—C1	108.65 (10)
C4—C5—H5	119.7	N1—S1—C1	106.11 (10)
C6—C5—H5	119.7
S1—N1—C7—O3	−10.3 (3)	S1—C1—C2—C3	179.0 (2)
S1—N1—C7—C8	169.94 (15)	C4—C3—C2—C1	−1.4 (4)
C8—C13—C12—C11	0.0 (3)	C2—C1—C6—C5	−1.2 (4)
C10—C9—C8—C13	1.0 (4)	S1—C1—C6—C5	−178.49 (18)
C10—C9—C8—C7	−179.8 (2)	C4—C5—C6—C1	0.4 (4)
C12—C13—C8—C9	−0.6 (3)	O4—C11—C10—C9	−178.6 (2)
C12—C13—C8—C7	−179.8 (2)	C12—C11—C10—C9	0.1 (4)
O3—C7—C8—C9	−2.4 (3)	C8—C9—C10—C11	−0.7 (4)
N1—C7—C8—C9	177.3 (2)	C7—N1—S1—O2	−177.30 (19)
O3—C7—C8—C13	176.8 (2)	C7—N1—S1—O1	−48.9 (2)
N1—C7—C8—C13	−3.5 (3)	C7—N1—S1—C1	68.0 (2)
C14—O4—C11—C10	−6.6 (4)	C6—C1—S1—O2	153.0 (2)
C14—O4—C11—C12	174.7 (3)	C2—C1—S1—O2	−24.3 (2)
C13—C12—C11—O4	179.0 (2)	C6—C1—S1—O1	21.4 (2)
C13—C12—C11—C10	0.2 (4)	C2—C1—S1—O1	−155.9 (2)
C2—C3—C4—C5	0.6 (4)	C6—C1—S1—N1	−95.9 (2)
C6—C5—C4—C3	−0.1 (4)	C2—C1—S1—N1	86.8 (2)
C6—C1—C2—C3	1.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1i	0.83 (3)	2.41 (3)	3.1662 (3)	153
C12—H12···O2ii	0.93	2.58	3.286 (3)	133
C4—H4···Cgiii	0.93	2.90	3.7396	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the meth­oxy­benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O1i	0.83 (3)	2.41 (3)	3.1662 (3)	153
C12—H12⋯O2ii	0.93	2.58	3.286 (3)	133
C4—H4⋯Cg iii	0.93	2.90	3.7396	150

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