N-(4-Methyl-phenyl-sulfon-yl)-3-nitro-benzamide.

In the title compound, C14H12N2O5S, the dihedral angle between the aromatic rings is 86.29 (1)° and the conformation between the C=O bond of the amide group and the meta-NO2 group is syn. The C-S-N-C torsion angle is -65.87 (19)° and the mol-ecule has an L-shaped conformation. In the crystal, the mol-ecules are connected into inversion dimers through pairs of N-H⋯O hydrogen bonds and C-H⋯O inter-actions forming R 2 (2)(8) and R 2 (2)(14) loops, respectively. The dimers are connected by further C-H⋯O inter-actions, thereby forming (100) sheets.

Related literature

For related structures see: Suchetan et al. (2010 ▶, 2011 ▶, 2012 ▶).

Experimental

Crystal data

C14H12N2O5S

M = 320.32

Monoclinic,

a = 4.9736 (5) Å

b = 23.245 (2) Å

c = 12.7197 (11) Å

β = 100.820 (4)°

V = 1444.4 (2) Å3

Z = 4

Cu Kα radiation

μ = 2.24 mm−1

T = 293 K

0.39 × 0.29 × 0.20 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.481, T max = 0.638

12115 measured reflections

2378 independent reflections

2053 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.114

S = 1.06

2378 reflections

204 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.23 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. DOI: 10.1107/S1600536814001317/hb7184sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001317/hb7184Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001317/hb7184Isup3.cml

CCDC reference:

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

C14H12N2O5S	Prism
Mr = 320.32	Dx = 1.473 Mg m−3
Monoclinic, P21/c	Melting point: 459 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 4.9736 (5) Å	Cell parameters from 1127 reflections
b = 23.245 (2) Å	θ = 3.8–64.5°
c = 12.7197 (11) Å	µ = 2.24 mm−1
β = 100.820 (4)°	T = 293 K
V = 1444.4 (2) Å3	Prism, colourless
Z = 4	0.39 × 0.29 × 0.20 mm
F(000) = 664

Bruker APEXII diffractometer	2053 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 64.5°, θmin = 3.8°
phi and φ scans	h = −5→4
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −26→26
Tmin = 0.481, Tmax = 0.638	l = −14→14
12115 measured reflections	2 standard reflections every 1 reflections
2378 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.3691P] where P = (Fo2 + 2Fc2)/3
2378 reflections	(Δ/σ)max < 0.001
204 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.23 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
S1	1.10155 (10)	0.50190 (2)	0.32699 (4)	0.0546 (2)
C8	0.6073 (4)	0.63811 (8)	0.33442 (15)	0.0481 (5)
C9	0.4226 (4)	0.66836 (8)	0.25927 (16)	0.0481 (5)
H9	0.4108	0.6615	0.1865	0.058*
O2	1.1994 (3)	0.47252 (7)	0.42557 (13)	0.0667 (4)
N2	0.0629 (4)	0.74082 (8)	0.21424 (15)	0.0570 (4)
O1	1.2908 (3)	0.52526 (7)	0.26821 (15)	0.0720 (5)
N1	0.9164 (4)	0.55519 (7)	0.36288 (16)	0.0534 (4)
C10	0.2572 (4)	0.70859 (8)	0.29425 (15)	0.0471 (5)
O3	0.8066 (3)	0.59550 (7)	0.19878 (13)	0.0695 (5)
O4	−0.1159 (4)	0.76822 (9)	0.24399 (15)	0.0891 (6)
O5	0.0900 (4)	0.73809 (9)	0.12131 (13)	0.0853 (6)
C4	0.4935 (5)	0.38740 (9)	0.11605 (18)	0.0593 (5)
C3	0.5450 (5)	0.38158 (10)	0.22531 (18)	0.0646 (6)
H3	0.4508	0.3537	0.2563	0.077*
C7	0.7819 (4)	0.59512 (9)	0.29113 (17)	0.0518 (5)
C5	0.6344 (5)	0.42936 (10)	0.07092 (18)	0.0680 (6)
H5	0.6014	0.4341	−0.0030	0.082*
C11	0.2669 (5)	0.71991 (9)	0.40117 (17)	0.0583 (5)
H11	0.1494	0.7467	0.4229	0.070*
C1	0.8710 (4)	0.45716 (8)	0.24416 (16)	0.0490 (5)
C6	0.8239 (5)	0.46431 (10)	0.13467 (19)	0.0630 (6)
H6	0.9182	0.4923	0.1039	0.076*
C13	0.6243 (5)	0.64965 (9)	0.44227 (17)	0.0602 (6)
H13	0.7500	0.6298	0.4928	0.072*
C2	0.7316 (5)	0.41580 (10)	0.29029 (17)	0.0588 (5)
H2	0.7635	0.4111	0.3642	0.071*
C12	0.4558 (5)	0.69042 (10)	0.47530 (18)	0.0669 (6)
H12	0.4696	0.6981	0.5479	0.080*
C14	0.2854 (6)	0.34997 (12)	0.0463 (2)	0.0845 (8)
H14A	0.1814	0.3292	0.0903	0.127*
H14B	0.3776	0.3232	0.0078	0.127*
H14C	0.1647	0.3736	−0.0035	0.127*
HN1	0.860 (5)	0.5495 (10)	0.417 (2)	0.062 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0368 (3)	0.0518 (3)	0.0732 (4)	0.0021 (2)	0.0053 (2)	−0.0047 (2)
C8	0.0445 (11)	0.0416 (10)	0.0566 (11)	−0.0023 (8)	0.0052 (9)	−0.0015 (8)
C9	0.0469 (11)	0.0478 (11)	0.0488 (10)	−0.0051 (9)	0.0071 (8)	−0.0001 (8)
O2	0.0538 (9)	0.0660 (10)	0.0726 (10)	0.0159 (7)	−0.0079 (7)	−0.0034 (8)
N2	0.0582 (11)	0.0534 (10)	0.0563 (11)	0.0032 (9)	0.0024 (8)	0.0041 (8)
O1	0.0428 (8)	0.0662 (10)	0.1106 (13)	−0.0065 (7)	0.0238 (8)	−0.0066 (9)
N1	0.0444 (10)	0.0513 (10)	0.0627 (11)	0.0046 (8)	0.0053 (8)	−0.0017 (8)
C10	0.0458 (11)	0.0423 (10)	0.0508 (11)	−0.0017 (8)	0.0027 (8)	0.0028 (8)
O3	0.0759 (11)	0.0679 (10)	0.0705 (11)	0.0121 (8)	0.0292 (8)	0.0079 (8)
O4	0.0871 (13)	0.0949 (14)	0.0821 (12)	0.0449 (11)	0.0077 (10)	0.0063 (10)
O5	0.0957 (14)	0.1043 (14)	0.0529 (10)	0.0235 (11)	0.0063 (9)	0.0148 (9)
C4	0.0611 (13)	0.0514 (12)	0.0619 (13)	0.0011 (10)	0.0025 (10)	−0.0020 (10)
C3	0.0647 (14)	0.0599 (13)	0.0669 (14)	−0.0144 (11)	0.0066 (11)	0.0075 (11)
C7	0.0448 (11)	0.0488 (11)	0.0612 (13)	−0.0026 (9)	0.0084 (9)	−0.0004 (9)
C5	0.0866 (17)	0.0651 (14)	0.0516 (12)	−0.0038 (12)	0.0111 (11)	−0.0008 (10)
C11	0.0665 (14)	0.0519 (11)	0.0551 (12)	0.0116 (10)	0.0082 (10)	−0.0036 (9)
C1	0.0414 (11)	0.0471 (10)	0.0587 (12)	0.0034 (8)	0.0100 (8)	−0.0014 (9)
C6	0.0686 (15)	0.0589 (13)	0.0647 (13)	−0.0080 (11)	0.0207 (11)	0.0028 (10)
C13	0.0670 (14)	0.0536 (12)	0.0540 (12)	0.0093 (10)	−0.0041 (10)	0.0001 (9)
C2	0.0591 (13)	0.0605 (13)	0.0546 (12)	−0.0081 (10)	0.0054 (10)	0.0051 (10)
C12	0.0871 (17)	0.0623 (14)	0.0471 (11)	0.0166 (12)	0.0017 (11)	−0.0057 (10)
C14	0.096 (2)	0.0701 (16)	0.0780 (17)	−0.0173 (14)	−0.0082 (14)	−0.0066 (13)

S1—O1	1.4156 (17)	C4—C14	1.507 (3)
S1—O2	1.4305 (16)	C3—C2	1.375 (3)
S1—N1	1.6580 (18)	C3—H3	0.9300
S1—C1	1.747 (2)	C5—C6	1.385 (3)
C8—C13	1.385 (3)	C5—H5	0.9300
C8—C9	1.386 (3)	C11—C12	1.382 (3)
C8—C7	1.495 (3)	C11—H11	0.9300
C9—C10	1.373 (3)	C1—C6	1.378 (3)
C9—H9	0.9300	C1—C2	1.379 (3)
N2—O4	1.211 (2)	C6—H6	0.9300
N2—O5	1.216 (2)	C13—C12	1.382 (3)
N2—C10	1.470 (3)	C13—H13	0.9300
N1—C7	1.383 (3)	C2—H2	0.9300
N1—HN1	0.80 (2)	C12—H12	0.9300
C10—C11	1.377 (3)	C14—H14A	0.9600
O3—C7	1.204 (3)	C14—H14B	0.9600
C4—C3	1.372 (3)	C14—H14C	0.9600
C4—C5	1.387 (3)
O1—S1—O2	119.71 (11)	N1—C7—C8	116.62 (19)
O1—S1—N1	108.51 (10)	C6—C5—C4	120.8 (2)
O2—S1—N1	103.33 (10)	C6—C5—H5	119.6
O1—S1—C1	109.63 (10)	C4—C5—H5	119.6
O2—S1—C1	108.74 (10)	C10—C11—C12	118.2 (2)
N1—S1—C1	105.96 (9)	C10—C11—H11	120.9
C13—C8—C9	119.62 (18)	C12—C11—H11	120.9
C13—C8—C7	124.23 (18)	C6—C1—C2	120.7 (2)
C9—C8—C7	116.14 (18)	C6—C1—S1	120.36 (16)
C10—C9—C8	118.78 (18)	C2—C1—S1	118.94 (16)
C10—C9—H9	120.6	C1—C6—C5	119.3 (2)
C8—C9—H9	120.6	C1—C6—H6	120.4
O4—N2—O5	123.57 (19)	C5—C6—H6	120.4
O4—N2—C10	118.53 (19)	C12—C13—C8	120.42 (19)
O5—N2—C10	117.89 (18)	C12—C13—H13	119.8
C7—N1—S1	123.00 (17)	C8—C13—H13	119.8
C7—N1—HN1	118.4 (18)	C3—C2—C1	119.0 (2)
S1—N1—HN1	114.5 (17)	C3—C2—H2	120.5
C9—C10—C11	122.56 (18)	C1—C2—H2	120.5
C9—C10—N2	118.58 (17)	C11—C12—C13	120.4 (2)
C11—C10—N2	118.86 (18)	C11—C12—H12	119.8
C3—C4—C5	118.4 (2)	C13—C12—H12	119.8
C3—C4—C14	121.1 (2)	C4—C14—H14A	109.5
C5—C4—C14	120.5 (2)	C4—C14—H14B	109.5
C4—C3—C2	121.9 (2)	H14A—C14—H14B	109.5
C4—C3—H3	119.0	C4—C14—H14C	109.5
C2—C3—H3	119.0	H14A—C14—H14C	109.5
O3—C7—N1	121.6 (2)	H14B—C14—H14C	109.5
O3—C7—C8	121.82 (19)
C13—C8—C9—C10	−1.0 (3)	C14—C4—C5—C6	179.3 (2)
C7—C8—C9—C10	−179.78 (17)	C9—C10—C11—C12	1.7 (3)
O1—S1—N1—C7	51.79 (19)	N2—C10—C11—C12	−178.2 (2)
O2—S1—N1—C7	179.85 (17)	O1—S1—C1—C6	−23.4 (2)
C1—S1—N1—C7	−65.87 (19)	O2—S1—C1—C6	−155.95 (17)
C8—C9—C10—C11	−0.3 (3)	N1—S1—C1—C6	93.55 (19)
C8—C9—C10—N2	179.61 (17)	O1—S1—C1—C2	158.45 (17)
O4—N2—C10—C9	166.6 (2)	O2—S1—C1—C2	25.9 (2)
O5—N2—C10—C9	−12.9 (3)	N1—S1—C1—C2	−84.63 (19)
O4—N2—C10—C11	−13.5 (3)	C2—C1—C6—C5	−0.1 (3)
O5—N2—C10—C11	167.0 (2)	S1—C1—C6—C5	−178.20 (18)
C5—C4—C3—C2	−0.3 (4)	C4—C5—C6—C1	−0.2 (4)
C14—C4—C3—C2	−179.2 (2)	C9—C8—C13—C12	1.0 (3)
S1—N1—C7—O3	−4.9 (3)	C7—C8—C13—C12	179.6 (2)
S1—N1—C7—C8	175.83 (14)	C4—C3—C2—C1	0.0 (4)
C13—C8—C7—O3	−162.5 (2)	C6—C1—C2—C3	0.2 (3)
C9—C8—C7—O3	16.1 (3)	S1—C1—C2—C3	178.32 (18)
C13—C8—C7—N1	16.8 (3)	C10—C11—C12—C13	−1.7 (4)
C9—C8—C7—N1	−164.58 (18)	C8—C13—C12—C11	0.4 (4)
C3—C4—C5—C6	0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O2i	0.80 (3)	2.14 (3)	2.927 (3)	167
C13—H13···O2i	0.93	2.59	3.333 (3)	137
C3—H3···O4ii	0.93	2.58	3.459 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O2i	0.80 (3)	2.14 (3)	2.927 (3)	167
C13—H13⋯O2i	0.93	2.59	3.333 (3)	137
C3—H3⋯O4ii	0.93	2.58	3.459 (3)	155

Symmetry codes: (i) ; (ii) .