4-Meth-oxy-N-[(4-methyl-phen-yl)sulfon-yl]benzamide including an unknown solvate.

In the title compound, C15H15NO4S, the dihedral angle between the benzene rings is 78.62 (16)°. In the crystal, adjacent mol-ecules are linked along the c axis into C(4) chains through strong N-H⋯O hydrogen bonds. Mol-ecules are further connected through C-H⋯O hydrogen bonds into a hexa-meric unit generating an R (6) 6(66) motif. Another C-H⋯O inter-action connects the mol-ecules along the c axis, forming C(5) chains. A region of disordered electron density, most probably disordered methanol-water solvent mol-ecules, was treated with the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155]. The formula mass and unit-cell characteristics do not take into account this disordered solvent.

Related literature

For similar structures, see: Gowda et al. (2009 ▶); Suchetan et al. (2010a ▶,b ▶,c ▶, 2011 ▶); Sreenivasa et al. (2013 ▶). For details of the use of the SQUEEZE routine in PLATON, see: Spek (2009 ▶).

Experimental

Crystal data

C15H15NO4S

M = 305.34

Trigonal,

a = 27.1686 (16) Å

c = 10.8594 (6) Å

V = 6941.8 (7) Å3

Z = 18

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.32 × 0.27 × 0.19 mm

Data collection

Bruker APEXII diffractometer

7701 measured reflections

2106 independent reflections

1604 reflections with I > 2σ(I)

R int = 0.031

θmax = 22.9°

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.06

2106 reflections

196 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.31 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/S1600536813028158/su2649sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028158/su2649Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028158/su2649Isup3.cml

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

C15H15NO4S	Dx = 1.315 Mg m−3
Mr = 305.34	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 1123 reflections
Hall symbol: -R 3	θ = 0.0–22.9°
a = 27.1686 (16) Å	µ = 0.22 mm−1
c = 10.8594 (6) Å	T = 293 K
V = 6941.8 (7) Å3	Prism, colourless
Z = 18	0.32 × 0.27 × 0.19 mm
F(000) = 2880

Bruker APEXII diffractometer	1604 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 22.9°, θmin = 1.5°
phi and ω scans	h = −28→27
7701 measured reflections	k = −29→27
2106 independent reflections	l = −11→11

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) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.050P)2 + 5.9239P] where P = (Fo2 + 2Fc2)/3
2106 reflections	(Δ/σ)max = 0.001
196 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.64344 (3)	0.92841 (3)	0.07169 (6)	0.0512 (3)
O2	0.67632 (8)	0.92727 (8)	0.17255 (17)	0.0630 (6)
O3	0.58608 (8)	0.93575 (8)	0.29224 (17)	0.0589 (6)
C9	0.57569 (10)	1.01361 (10)	0.2290 (2)	0.0408 (6)
N1	0.61811 (10)	0.97065 (10)	0.1035 (2)	0.0485 (6)
H1N	0.6281 (12)	0.9968 (9)	0.055 (2)	0.062 (10)*
O1	0.66938 (8)	0.94701 (8)	−0.04522 (17)	0.0632 (6)
O4	0.52572 (9)	1.13258 (9)	0.2828 (2)	0.0741 (7)
C8	0.59338 (10)	0.97057 (11)	0.2137 (2)	0.0432 (7)
C10	0.57316 (11)	1.04599 (11)	0.1330 (2)	0.0492 (7)
H10	0.5831	1.0413	0.0538	0.059*
C12	0.54143 (11)	1.09243 (11)	0.2710 (3)	0.0504 (7)
C14	0.56081 (11)	1.02166 (11)	0.3456 (2)	0.0506 (7)
H14	0.5625	1.0004	0.4107	0.061*
C11	0.55601 (12)	1.08497 (12)	0.1542 (3)	0.0555 (8)
H11	0.5543	1.1064	0.0893	0.067*
C13	0.54340 (11)	1.06075 (12)	0.3676 (3)	0.0543 (8)
H13	0.5332	1.0655	0.4465	0.065*
C1	0.58283 (12)	0.86088 (12)	0.0570 (2)	0.0506 (7)
C3	0.53039 (16)	0.76272 (14)	0.1127 (3)	0.0733 (9)
H3	0.5270	0.7326	0.1598	0.088*
C6	0.54185 (13)	0.85199 (13)	−0.0290 (3)	0.0591 (8)
H6	0.5458	0.8817	−0.0784	0.071*
C2	0.57735 (14)	0.81618 (14)	0.1276 (3)	0.0640 (9)
H2	0.6052	0.8220	0.1850	0.077*
C5	0.49512 (14)	0.79869 (14)	−0.0406 (3)	0.0689 (9)
H5	0.4670	0.7929	−0.0972	0.083*
C4	0.48878 (14)	0.75366 (14)	0.0291 (3)	0.0678 (9)
C15	0.50425 (16)	1.13869 (16)	0.3982 (3)	0.0871 (11)
H15A	0.4715	1.1032	0.4206	0.131*
H15B	0.4938	1.1675	0.3915	0.131*
H15C	0.5330	1.1495	0.4602	0.131*
C7	0.43705 (17)	0.69489 (15)	0.0145 (4)	0.1057 (14)
H7A	0.4150	0.6948	−0.0546	0.159*	0.50
H7B	0.4143	0.6851	0.0878	0.159*	0.50
H7C	0.4491	0.6676	0.0011	0.159*	0.50
H7D	0.4373	0.6702	0.0775	0.159*	0.50
H7E	0.4380	0.6799	−0.0649	0.159*	0.50
H7F	0.4031	0.6974	0.0218	0.159*	0.50

	U11	U22	U33	U12	U13	U23
S1	0.0582 (5)	0.0608 (5)	0.0468 (5)	0.0389 (4)	0.0014 (4)	−0.0045 (3)
O2	0.0687 (13)	0.0786 (14)	0.0612 (13)	0.0515 (12)	−0.0164 (10)	−0.0147 (11)
O3	0.0789 (14)	0.0686 (13)	0.0476 (12)	0.0506 (11)	0.0087 (10)	0.0122 (10)
C9	0.0383 (15)	0.0458 (15)	0.0404 (15)	0.0226 (13)	−0.0015 (12)	−0.0007 (12)
N1	0.0642 (16)	0.0548 (15)	0.0397 (14)	0.0396 (13)	0.0062 (12)	0.0032 (12)
O1	0.0702 (13)	0.0730 (13)	0.0552 (13)	0.0423 (11)	0.0176 (11)	0.0014 (10)
O4	0.0859 (15)	0.0791 (15)	0.0861 (17)	0.0629 (14)	−0.0009 (12)	−0.0053 (12)
C8	0.0431 (16)	0.0488 (17)	0.0395 (16)	0.0243 (14)	−0.0013 (13)	−0.0007 (13)
C10	0.0507 (17)	0.0638 (19)	0.0421 (16)	0.0353 (15)	0.0030 (13)	0.0049 (14)
C12	0.0429 (16)	0.0537 (18)	0.063 (2)	0.0305 (14)	−0.0057 (14)	−0.0041 (15)
C14	0.0595 (18)	0.0636 (18)	0.0401 (16)	0.0394 (16)	0.0035 (14)	0.0045 (14)
C11	0.0605 (18)	0.068 (2)	0.0528 (19)	0.0431 (17)	0.0042 (14)	0.0140 (15)
C13	0.0551 (18)	0.070 (2)	0.0477 (17)	0.0385 (16)	0.0015 (14)	−0.0099 (15)
C1	0.0648 (19)	0.0591 (18)	0.0426 (16)	0.0421 (16)	0.0018 (14)	−0.0019 (14)
C3	0.100 (3)	0.059 (2)	0.067 (2)	0.045 (2)	0.007 (2)	0.0091 (17)
C6	0.069 (2)	0.062 (2)	0.0522 (19)	0.0367 (18)	−0.0046 (16)	0.0035 (15)
C2	0.085 (2)	0.073 (2)	0.0542 (19)	0.054 (2)	−0.0054 (17)	−0.0012 (17)
C5	0.067 (2)	0.074 (2)	0.064 (2)	0.0334 (19)	−0.0101 (17)	−0.0020 (18)
C4	0.075 (2)	0.061 (2)	0.063 (2)	0.0308 (18)	0.0086 (18)	0.0005 (17)
C15	0.099 (3)	0.102 (3)	0.094 (3)	0.076 (2)	−0.005 (2)	−0.030 (2)
C7	0.102 (3)	0.075 (3)	0.107 (3)	0.019 (2)	0.015 (2)	0.003 (2)

S1—O1	1.4169 (19)	C1—C6	1.379 (4)
S1—O2	1.4235 (19)	C1—C2	1.380 (4)
S1—N1	1.643 (2)	C3—C4	1.373 (4)
S1—C1	1.756 (3)	C3—C2	1.382 (4)
O3—C8	1.214 (3)	C3—H3	0.9300
C9—C14	1.380 (3)	C6—C5	1.373 (4)
C9—C10	1.388 (3)	C6—H6	0.9300
C9—C8	1.479 (4)	C2—H2	0.9300
N1—C8	1.372 (3)	C5—C4	1.374 (4)
N1—H1N	0.817 (17)	C5—H5	0.9300
O4—C12	1.362 (3)	C4—C7	1.519 (5)
O4—C15	1.427 (4)	C15—H15A	0.9600
C10—C11	1.373 (4)	C15—H15B	0.9600
C10—H10	0.9300	C15—H15C	0.9600
C12—C11	1.374 (4)	C7—H7A	0.9600
C12—C13	1.375 (4)	C7—H7B	0.9600
C14—C13	1.382 (4)	C7—H7C	0.9600
C14—H14	0.9300	C7—H7D	0.9600
C11—H11	0.9300	C7—H7E	0.9600
C13—H13	0.9300	C7—H7F	0.9600
O1—S1—O2	119.45 (13)	C5—C6—H6	120.4
O1—S1—N1	104.29 (12)	C1—C6—H6	120.4
O2—S1—N1	109.86 (11)	C1—C2—C3	119.8 (3)
O1—S1—C1	109.32 (12)	C1—C2—H2	120.1
O2—S1—C1	108.53 (13)	C3—C2—H2	120.1
N1—S1—C1	104.33 (13)	C6—C5—C4	121.7 (3)
C14—C9—C10	118.5 (2)	C6—C5—H5	119.1
C14—C9—C8	117.7 (2)	C4—C5—H5	119.1
C10—C9—C8	123.8 (2)	C3—C4—C5	118.6 (3)
C8—N1—S1	123.9 (2)	C3—C4—C7	120.2 (3)
C8—N1—H1N	121 (2)	C5—C4—C7	121.1 (3)
S1—N1—H1N	113 (2)	O4—C15—H15A	109.5
C12—O4—C15	119.1 (2)	O4—C15—H15B	109.5
O3—C8—N1	120.2 (2)	H15A—C15—H15B	109.5
O3—C8—C9	123.1 (2)	O4—C15—H15C	109.5
N1—C8—C9	116.7 (2)	H15A—C15—H15C	109.5
C11—C10—C9	120.5 (3)	H15B—C15—H15C	109.5
C11—C10—H10	119.8	C4—C7—H7A	109.5
C9—C10—H10	119.8	C4—C7—H7B	109.5
O4—C12—C11	115.7 (3)	H7A—C7—H7B	109.5
O4—C12—C13	123.8 (3)	C4—C7—H7C	109.5
C11—C12—C13	120.5 (2)	H7A—C7—H7C	109.5
C9—C14—C13	121.4 (3)	H7B—C7—H7C	109.5
C9—C14—H14	119.3	C4—C7—H7D	109.5
C13—C14—H14	119.3	H7A—C7—H7D	141.1
C10—C11—C12	120.2 (3)	H7B—C7—H7D	56.3
C10—C11—H11	119.9	H7C—C7—H7D	56.3
C12—C11—H11	119.9	C4—C7—H7E	109.5
C12—C13—C14	119.0 (3)	H7A—C7—H7E	56.3
C12—C13—H13	120.5	H7B—C7—H7E	141.1
C14—C13—H13	120.5	H7C—C7—H7E	56.3
C6—C1—C2	120.0 (3)	H7D—C7—H7E	109.5
C6—C1—S1	119.9 (2)	C4—C7—H7F	109.5
C2—C1—S1	120.1 (2)	H7A—C7—H7F	56.3
C4—C3—C2	120.7 (3)	H7B—C7—H7F	56.3
C4—C3—H3	119.7	H7C—C7—H7F	141.1
C2—C3—H3	119.7	H7D—C7—H7F	109.5
C5—C6—C1	119.1 (3)	H7E—C7—H7F	109.5
O1—S1—N1—C8	−174.5 (2)	C11—C12—C13—C14	0.6 (4)
O2—S1—N1—C8	−45.3 (3)	C9—C14—C13—C12	−0.5 (4)
C1—S1—N1—C8	70.9 (2)	O1—S1—C1—C6	−52.8 (2)
S1—N1—C8—O3	−4.4 (4)	O2—S1—C1—C6	175.4 (2)
S1—N1—C8—C9	176.81 (18)	N1—S1—C1—C6	58.3 (2)
C14—C9—C8—O3	13.2 (4)	O1—S1—C1—C2	124.4 (2)
C10—C9—C8—O3	−166.6 (3)	O2—S1—C1—C2	−7.4 (3)
C14—C9—C8—N1	−168.0 (2)	N1—S1—C1—C2	−124.5 (2)
C10—C9—C8—N1	12.1 (4)	C2—C1—C6—C5	1.8 (4)
C14—C9—C10—C11	−0.2 (4)	S1—C1—C6—C5	179.0 (2)
C8—C9—C10—C11	179.7 (2)	C6—C1—C2—C3	−0.7 (4)
C15—O4—C12—C11	173.4 (3)	S1—C1—C2—C3	−177.9 (2)
C15—O4—C12—C13	−6.9 (4)	C4—C3—C2—C1	−0.6 (5)
C10—C9—C14—C13	0.3 (4)	C1—C6—C5—C4	−1.6 (5)
C8—C9—C14—C13	−179.5 (2)	C2—C3—C4—C5	0.8 (5)
C9—C10—C11—C12	0.3 (4)	C2—C3—C4—C7	−179.3 (3)
O4—C12—C11—C10	179.2 (2)	C6—C5—C4—C3	0.3 (5)
C13—C12—C11—C10	−0.5 (4)	C6—C5—C4—C7	−179.6 (3)
O4—C12—C13—C14	−179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.82 (2)	2.26 (2)	3.038 (3)	160 (3)
N1—H1N···O2i	0.82 (2)	2.59 (3)	3.140 (3)	126 (2)
C10—H10···O3i	0.93	2.58	3.249 (3)	129
C15—H15A···O1ii	0.96	2.56	3.454 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.82 (2)	2.26 (2)	3.038 (3)	160 (3)
N1—H1N⋯O2i	0.82 (2)	2.59 (3)	3.140 (3)	126 (2)
C10—H10⋯O3i	0.93	2.58	3.249 (3)	129
C15—H15A⋯O1ii	0.96	2.56	3.454 (4)	154

Symmetry codes: (i) ; (ii) .