4-Nitro-N-phenyl­benzene­sulfonamide

In the title compound, C₁₂H₁₀N₂O₄S, the dihedral angle between the aromatic rings is 36.19 (18)°. In the crystal, N—H...O hydrogen bonds link the mol­ecules into C(4) chains running along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.037
• wR factor = 0.086
• Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT915_ALERT_3_B Low Friedel Pair Coverage ......................         25 Perc.

Author Response: We feel that the Flack parameter is correct enough and presented structural information on this compound is reliable enough in order to unambigiously solve the structure and refine the structure model reliably.

Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0064 Ang
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.33
           From the CIF: _reflns_number_total               1421
           Count of symmetry unique reflns         1142
           Completeness (_total/calc)            124.43%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       279
           Fraction of Friedel pairs measured     0.244
           Are heavy atom types Z>Si present        yes
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          78 Perc.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

As a part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Alkan et al., 2011; Gowda & Weiss, 1994; Shahwar et al., 2012); N-arylsulfonamides (Chaithanya et al., 2012; Gowda et al., 2003) and N-chloroarylsulfonamides (Gowda et al., 2005; Shetty & Gowda, 2004),in the present work, the crystal structure of N-(phenyl)-4-nitrobenzenesulfonamide has been determined (Fig. 1).

The conformation of the N—C bond in the —SO₂—NH—C segment has gauche torsions with respect to the S═O bonds (Fig.1). The molecule is twisted at the S—N bond with the torsional angle of 61.89 (32)°, compared to the value of -72.83 (15)° in N-(phenyl)-2-nitrobenzenesulfonamide (I)(Chaithanya et al., 2012).

The dihedral angle between the sulfonyl and the anilino rings is 36.19 (18)°, compared to the value of 59.55 (7)° in (I).

In the crystal, the intermolecular N—H···O hydrogen bond interactions link the molecules into C(4) chains. Part of the crystal structure is shown in Fig. 2.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al. (2011); Gowda & Weiss (1994); Shahwar et al. (2012), of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2003) and of N-chloroarylsulfonamides, see: Gowda et al. (2005); Shetty & Gowda (2004).

S2. Experimental

The title compound was prepared by treating 4-nitrobenzenesulfonylchloride with aniline in the stoichiometric ratio and boiling the reaction mixture for 15 minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid N-(phenyl)-4-nitrobenzenesulfonamide was filtered under suction and washed thoroughly with cold water and dilute HCl to remove the excess sulfonylchloride and aniline, respectively. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Plate like colourless single crystals of the title compound used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.

S3. Refinement

H atoms bonded to C were positioned with idealized geometry using a riding model with C—H = 0.93 Å. The coordinates of the amino H atom were refined with the N—H distance restrained to 0.86 (2) Å. All H atoms were refined with isotropic displacement parameters set at 1.2 U_eq of the parent atom.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

4-Nitro-N-phenylbenzenesulfonamide

Crystal data

C12H10N2O4S	F(000) = 576
Mr = 278.28	Dx = 1.490 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1242 reflections
a = 5.1948 (4) Å	θ = 3.2–27.6°
b = 12.8089 (9) Å	µ = 0.27 mm^−1
c = 18.682 (1) Å	T = 293 K
β = 93.419 (7)°	Plate, colourless
V = 1240.88 (15) Å^3	0.36 × 0.32 × 0.08 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1421 independent reflections
Radiation source: fine-focus sealed tube	1311 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Rotation method data acquisition using ω scans	θmax = 25.3°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→3
Tmin = 0.908, Tmax = 0.979	k = −5→15
2074 measured reflections	l = −22→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.032P)^2 + 0.9798P] where P = (Fo^2 + 2Fc^2)/3
S = 1.20	(Δ/σ)max < 0.001
1421 reflections	Δρmax = 0.25 e Å^−3
175 parameters	Δρmin = −0.16 e Å^−3
3 restraints	Absolute structure: Flack (1983), 282 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (12)

Special details

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0817 (7)	0.9140 (3)	0.0338 (2)	0.0425 (9)
C2	−0.0381 (8)	1.0097 (3)	0.0379 (2)	0.0535 (11)
H2	−0.1700	1.0195	0.0688	0.064*
C3	0.0406 (8)	1.0907 (3)	−0.0044 (2)	0.0570 (12)
H3	−0.0381	1.1558	−0.0026	0.068*
C4	0.2345 (8)	1.0741 (3)	−0.0487 (2)	0.0457 (9)
C5	0.3565 (9)	0.9789 (3)	−0.0540 (3)	0.0569 (11)
H5	0.4883	0.9697	−0.0849	0.068*
C6	0.2773 (8)	0.8980 (3)	−0.0120 (2)	0.0533 (11)
H6	0.3550	0.8328	−0.0146	0.064*
C7	0.1676 (8)	0.9283 (3)	0.2053 (2)	0.0457 (9)
C8	0.3323 (9)	1.0099 (3)	0.1962 (3)	0.0604 (12)
H8	0.4631	1.0034	0.1646	0.072*
C9	0.3052 (12)	1.1013 (4)	0.2335 (3)	0.0762 (15)
H9	0.4186	1.1564	0.2277	0.091*
C10	0.1108 (13)	1.1109 (4)	0.2793 (3)	0.0826 (17)
H10	0.0895	1.1734	0.3036	0.099*
C11	−0.0527 (11)	1.0291 (5)	0.2895 (3)	0.0825 (16)
H11	−0.1833	1.0358	0.3211	0.099*
C12	−0.0235 (9)	0.9362 (4)	0.2526 (2)	0.0658 (13)
H12	−0.1322	0.8800	0.2599	0.079*
N1	0.1932 (7)	0.8315 (2)	0.16574 (19)	0.0491 (8)
H1N	0.346 (5)	0.817 (3)	0.156 (2)	0.059*
N2	0.3232 (8)	1.1618 (3)	−0.0926 (2)	0.0624 (10)
O1	−0.2542 (5)	0.82835 (19)	0.11253 (16)	0.0535 (8)
O2	0.0826 (6)	0.71539 (19)	0.06472 (17)	0.0569 (8)
O3	0.2037 (8)	1.2437 (3)	−0.0919 (2)	0.0907 (13)
O4	0.5135 (8)	1.1485 (3)	−0.1263 (2)	0.0894 (13)
S2	0.00585 (16)	0.81293 (6)	0.09388 (7)	0.0445 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.037 (2)	0.0366 (16)	0.054 (2)	0.0000 (16)	0.0048 (17)	0.0008 (16)
C2	0.045 (2)	0.0422 (19)	0.076 (3)	0.0090 (18)	0.024 (2)	0.0009 (19)
C3	0.055 (3)	0.038 (2)	0.080 (3)	0.0115 (19)	0.017 (2)	0.005 (2)
C4	0.048 (2)	0.0387 (18)	0.051 (2)	−0.0031 (17)	0.0065 (18)	0.0020 (16)
C5	0.061 (3)	0.054 (2)	0.058 (3)	0.005 (2)	0.027 (2)	0.003 (2)
C6	0.054 (3)	0.042 (2)	0.066 (3)	0.0123 (19)	0.018 (2)	−0.0004 (19)
C7	0.047 (2)	0.0451 (19)	0.045 (2)	0.0006 (18)	0.0039 (18)	0.0022 (17)
C8	0.061 (3)	0.058 (2)	0.064 (3)	−0.006 (2)	0.016 (2)	−0.002 (2)
C9	0.104 (5)	0.051 (2)	0.074 (3)	−0.008 (3)	0.009 (3)	0.000 (2)
C10	0.104 (5)	0.078 (3)	0.066 (3)	0.017 (3)	0.004 (3)	−0.025 (3)
C11	0.072 (4)	0.115 (4)	0.062 (3)	0.007 (4)	0.022 (3)	−0.024 (3)
C12	0.061 (3)	0.087 (3)	0.051 (3)	−0.014 (2)	0.020 (2)	−0.007 (2)
N1	0.0428 (19)	0.0479 (18)	0.057 (2)	0.0060 (16)	0.0083 (16)	0.0036 (15)
N2	0.068 (3)	0.054 (2)	0.067 (3)	0.0027 (19)	0.016 (2)	0.0115 (17)
O1	0.0344 (15)	0.0529 (16)	0.074 (2)	−0.0013 (12)	0.0104 (14)	0.0027 (13)
O2	0.0585 (19)	0.0351 (13)	0.078 (2)	0.0002 (12)	0.0166 (16)	−0.0035 (12)
O3	0.109 (3)	0.0544 (18)	0.112 (3)	0.020 (2)	0.038 (3)	0.0257 (18)
O4	0.095 (3)	0.071 (2)	0.108 (3)	0.0060 (19)	0.053 (3)	0.027 (2)
S2	0.0383 (5)	0.0369 (4)	0.0592 (5)	−0.0003 (5)	0.0108 (4)	0.0004 (5)

Geometric parameters (Å, º)

C1—C2	1.379 (5)	C8—C9	1.375 (6)
C1—C6	1.383 (5)	C8—H8	0.9300
C1—S2	1.773 (4)	C9—C10	1.366 (7)
C2—C3	1.382 (5)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.369 (8)
C3—C4	1.358 (5)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.387 (7)
C4—C5	1.380 (5)	C11—H11	0.9300
C4—N2	1.480 (5)	C12—H12	0.9300
C5—C6	1.376 (5)	N1—S2	1.628 (4)
C5—H5	0.9300	N1—H1N	0.85 (2)
C6—H6	0.9300	N2—O4	1.215 (5)
C7—C8	1.368 (6)	N2—O3	1.220 (5)
C7—C12	1.371 (5)	O1—S2	1.429 (3)
C7—N1	1.454 (5)	O2—S2	1.429 (3)
C2—C1—C6	121.1 (3)	C10—C9—C8	119.7 (5)
C2—C1—S2	119.7 (3)	C10—C9—H9	120.1
C6—C1—S2	118.9 (3)	C8—C9—H9	120.1
C1—C2—C3	119.1 (4)	C9—C10—C11	120.4 (5)
C1—C2—H2	120.5	C9—C10—H10	119.8
C3—C2—H2	120.5	C11—C10—H10	119.8
C4—C3—C2	119.1 (3)	C10—C11—C12	120.0 (5)
C4—C3—H3	120.4	C10—C11—H11	120.0
C2—C3—H3	120.4	C12—C11—H11	120.0
C3—C4—C5	122.8 (3)	C7—C12—C11	119.2 (4)
C3—C4—N2	119.0 (4)	C7—C12—H12	120.4
C5—C4—N2	118.1 (4)	C11—C12—H12	120.4
C6—C5—C4	118.0 (4)	C7—N1—S2	118.4 (3)
C6—C5—H5	121.0	C7—N1—H1N	114 (3)
C4—C5—H5	121.0	S2—N1—H1N	108 (3)
C5—C6—C1	119.8 (3)	O4—N2—O3	123.7 (4)
C5—C6—H6	120.1	O4—N2—C4	118.1 (4)
C1—C6—H6	120.1	O3—N2—C4	118.1 (4)
C8—C7—C12	120.4 (4)	O1—S2—O2	120.20 (16)
C8—C7—N1	120.7 (4)	O1—S2—N1	107.82 (18)
C12—C7—N1	118.9 (4)	O2—S2—N1	106.00 (18)
C7—C8—C9	120.2 (5)	O1—S2—C1	107.61 (16)
C7—C8—H8	119.9	O2—S2—C1	108.63 (17)
C9—C8—H8	119.9	N1—S2—C1	105.71 (18)
C6—C1—C2—C3	−0.3 (7)	C10—C11—C12—C7	−1.0 (8)
S2—C1—C2—C3	173.8 (3)	C8—C7—N1—S2	−98.6 (4)
C1—C2—C3—C4	−0.3 (7)	C12—C7—N1—S2	82.0 (5)
C2—C3—C4—C5	0.6 (7)	C3—C4—N2—O4	172.7 (5)
C2—C3—C4—N2	−178.4 (4)	C5—C4—N2—O4	−6.3 (6)
C3—C4—C5—C6	−0.3 (7)	C3—C4—N2—O3	−6.2 (6)
N2—C4—C5—C6	178.7 (4)	C5—C4—N2—O3	174.8 (5)
C4—C5—C6—C1	−0.3 (7)	C7—N1—S2—O1	−53.0 (3)
C2—C1—C6—C5	0.6 (7)	C7—N1—S2—O2	177.1 (3)
S2—C1—C6—C5	−173.5 (4)	C7—N1—S2—C1	61.9 (3)
C12—C7—C8—C9	−1.0 (8)	C2—C1—S2—O1	29.2 (4)
N1—C7—C8—C9	179.5 (4)	C6—C1—S2—O1	−156.6 (3)
C7—C8—C9—C10	−0.8 (8)	C2—C1—S2—O2	160.8 (4)
C8—C9—C10—C11	1.7 (9)	C6—C1—S2—O2	−25.0 (4)
C9—C10—C11—C12	−0.8 (9)	C2—C1—S2—N1	−85.9 (4)
C8—C7—C12—C11	1.9 (7)	C6—C1—S2—N1	88.4 (4)
N1—C7—C12—C11	−178.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.85 (2)	2.28 (2)	3.094 (4)	162 (4)

Symmetry code: (i) x+1, y, z.