N,N-Bis(5-bromo-2-thienylsulfon­yl)-3-nitro­aniline

Lin, S.-M.; Zheng, M.; Xiong, J.

doi:10.1107/S1600536807024683

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N,N-Bis(5-bromo-2-thienylsulfonyl)-3-nitroaniline

S.-M. Lin, M. Zheng and J. Xiong

In the title compound, C₁₄H₈Br₂N₂O₆S₄, all bond lengths and angles are within normal ranges. The benzene ring and the two thiophene rings make dihedral angles of 35.97 (15) and 37.92 (19)°, and the dihedral angle between the two thiophene rings is 62.47 (14)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024683/cf2106sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024683/cf2106Isup2.hkl Contains datablock I

CCDC reference: 654928

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R factor = 0.036
wR factor = 0.095
Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.98 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N2
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br2    ..  O5      ..       3.05 Ang.

Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT213_ALERT_2_C Atom O5      has ADP max/min Ratio .............       3.10 prola
PLAT213_ALERT_2_C Atom O6      has ADP max/min Ratio .............       3.80 prola
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       2.71 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.18
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O6      ..       3.33 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O3      ..       3.36 Ang.

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

Comment top

Some sulfonamide compounds exhibit germicidal activities (Gayathri et al., 2006; Krishnaiah et al., 1995; Yu, 2006). Some crystal structures involving sulfonamide groups have been published, including a recent report from our laboratory (Yan et al., 2007). As an extension of this research, we report here the synthesis and crystal structure of the title compound (I).

In (I) (Fig. 1), all bond lengths and angles show normal values (Allen et al., 1987) and are unremarkable when compared with those found in our previous report (Yan et al., 2007). The benzene ring (C5—C10) and the two thiophene groups (C1—C4/S1, C11—C14/S4) are essentially planar with r. m. s. deviations of 0.0025 Å, 0.0032 Å and 0.0036 Å each. The benzene ring and the two thiophene rings (C1—C4/S1, C11—C14/S4) make dihedral angles of 35.97 (15)° and 37.92 (19)°, respectively. The dihedral angle between the two thiophene rings is 62.47 (14)°.

Related literature top

For related literature, see Allen et al. (1987); Gayathri et al. (2006); Krishnaiah et al. (1995); Yan et al. (2007); Yu (2006).

Experimental top

5-Bromothiophene-2-sulfonyl chloride (5 mmol, 1.304) in ethyl acetate (20 ml) was added dropwise to 3-nitroaniline (5 mmol, 1.38 g) in acetone (20 ml) at room temperature. The pure solid product was obtained after 24 h reaction and column chromatographic separation. Single crystals were obtained from 95% ethanol after 10 days.

Structure description top

For related literature, see Allen et al. (1987); Gayathri et al. (2006); Krishnaiah et al. (1995); Yan et al. (2007); Yu (2006).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. Molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids at the 50% probability level.

N,N-Bis(5-bromo-2-thienylsulfonyl)-3-nitroaniline top

Crystal data top

C₁₄H₈Br₂N₂O₆S₄	Z = 2
M_r = 588.30	F(000) = 576
Triclinic, P1	D_x = 1.963 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5147 (7) Å	Cell parameters from 2347 reflections
b = 9.3674 (7) Å	θ = 2.4–25.0°
c = 13.7585 (11) Å	µ = 4.53 mm⁻¹
α = 103.109 (1)°	T = 298 K
β = 100.810 (1)°	Block, colorless
γ = 105.155 (1)°	0.29 × 0.26 × 0.21 mm
V = 995.42 (14) Å³

Data collection top

Bruker APEX area-detector diffractometer	3451 independent reflections
Radiation source: fine-focus sealed tube	2895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
φ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→10
T_min = 0.294, T_max = 0.392	k = −11→10
5264 measured reflections	l = −16→15

Refinement top

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0448P)² + 1.0353P] where P = (F_o² + 2F_c²)/3
3451 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₄H₈Br₂N₂O₆S₄	γ = 105.155 (1)°
M_r = 588.30	V = 995.42 (14) Å³
Triclinic, P1	Z = 2
a = 8.5147 (7) Å	Mo Kα radiation
b = 9.3674 (7) Å	µ = 4.53 mm⁻¹
c = 13.7585 (11) Å	T = 298 K
α = 103.109 (1)°	0.29 × 0.26 × 0.21 mm
β = 100.810 (1)°

Data collection top

Bruker APEX area-detector diffractometer	3451 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2895 reflections with I > 2σ(I)
T_min = 0.294, T_max = 0.392	R_int = 0.013
5264 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.02	Δρ_max = 0.57 e Å⁻³
3451 reflections	Δρ_min = −0.50 e Å⁻³
253 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.80658 (6)	0.57752 (6)	−0.01657 (3)	0.06367 (16)
Br2	0.16643 (7)	0.79432 (6)	0.73552 (3)	0.06776 (17)
S1	0.70495 (14)	0.75108 (11)	0.16962 (8)	0.0508 (3)
S2	0.56667 (11)	0.75343 (11)	0.35446 (7)	0.0415 (2)
S3	0.19996 (11)	0.59462 (10)	0.30359 (7)	0.0402 (2)
S4	0.24634 (15)	0.65019 (13)	0.53339 (8)	0.0549 (3)
O1	0.6610 (3)	0.9124 (3)	0.3806 (2)	0.0577 (7)
O2	0.5703 (4)	0.6730 (3)	0.4300 (2)	0.0583 (7)
O3	0.0704 (3)	0.5875 (3)	0.2195 (2)	0.0554 (7)
O4	0.2608 (4)	0.4679 (3)	0.3058 (2)	0.0553 (7)
O5	0.2349 (8)	0.8484 (5)	−0.0312 (3)	0.141 (2)
O6	0.2078 (12)	1.0655 (7)	−0.0019 (4)	0.220 (4)
N1	0.3660 (4)	0.7446 (3)	0.3097 (2)	0.0377 (6)
N2	0.2335 (8)	0.9620 (5)	0.0268 (3)	0.1021 (18)
C1	0.7121 (5)	0.5809 (5)	0.0948 (3)	0.0462 (9)
C2	0.6533 (5)	0.4597 (5)	0.1300 (3)	0.0544 (10)
H2	0.6492	0.3593	0.0987	0.065*
C3	0.5988 (5)	0.5025 (5)	0.2192 (3)	0.0521 (10)
H3	0.5536	0.4337	0.2536	0.062*
C4	0.6197 (4)	0.6552 (4)	0.2491 (3)	0.0412 (8)
C5	0.3332 (4)	0.8701 (4)	0.2738 (3)	0.0389 (8)
C6	0.3002 (5)	0.8562 (4)	0.1699 (3)	0.0489 (9)
H6	0.3000	0.7679	0.1224	0.059*
C7	0.2675 (7)	0.9768 (5)	0.1384 (3)	0.0620 (12)
C8	0.2669 (6)	1.1098 (5)	0.2055 (3)	0.0618 (12)
H8	0.2449	1.1897	0.1815	0.074*
C9	0.2998 (6)	1.1209 (5)	0.3093 (3)	0.0565 (11)
H9	0.2993	1.2093	0.3564	0.068*
C10	0.3337 (5)	1.0025 (4)	0.3444 (3)	0.0472 (9)
H10	0.3566	1.0112	0.4147	0.057*
C11	0.1428 (4)	0.6570 (4)	0.4158 (3)	0.0408 (8)
C12	0.0271 (5)	0.7303 (5)	0.4243 (3)	0.0580 (11)
H12	−0.0394	0.7456	0.3683	0.070*
C13	0.0170 (5)	0.7811 (6)	0.5264 (3)	0.0619 (11)
H13	−0.0566	0.8329	0.5460	0.074*
C14	0.1281 (5)	0.7448 (4)	0.5924 (3)	0.0482 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0770 (3)	0.0778 (3)	0.0497 (3)	0.0413 (3)	0.0284 (2)	0.0152 (2)
Br2	0.0943 (4)	0.0683 (3)	0.0411 (2)	0.0204 (3)	0.0258 (2)	0.0162 (2)
S1	0.0673 (7)	0.0480 (5)	0.0455 (6)	0.0249 (5)	0.0244 (5)	0.0139 (4)
S2	0.0417 (5)	0.0467 (5)	0.0323 (5)	0.0134 (4)	0.0067 (4)	0.0076 (4)
S3	0.0446 (5)	0.0374 (5)	0.0342 (5)	0.0087 (4)	0.0082 (4)	0.0090 (4)
S4	0.0752 (7)	0.0623 (6)	0.0394 (5)	0.0343 (6)	0.0164 (5)	0.0224 (5)
O1	0.0503 (16)	0.0471 (15)	0.0572 (18)	0.0034 (13)	0.0109 (13)	−0.0036 (13)
O2	0.0656 (18)	0.0781 (19)	0.0389 (15)	0.0320 (15)	0.0112 (13)	0.0234 (14)
O3	0.0511 (16)	0.0652 (18)	0.0363 (14)	0.0059 (13)	0.0010 (12)	0.0120 (13)
O4	0.0740 (19)	0.0354 (13)	0.0612 (18)	0.0190 (13)	0.0255 (15)	0.0147 (12)
O5	0.312 (7)	0.120 (3)	0.044 (2)	0.141 (4)	0.060 (3)	0.034 (2)
O6	0.531 (14)	0.148 (5)	0.076 (3)	0.213 (7)	0.104 (6)	0.073 (3)
N1	0.0404 (16)	0.0373 (15)	0.0401 (16)	0.0140 (13)	0.0133 (13)	0.0159 (13)
N2	0.213 (6)	0.078 (3)	0.056 (3)	0.085 (4)	0.053 (3)	0.041 (2)
C1	0.045 (2)	0.056 (2)	0.040 (2)	0.0260 (18)	0.0100 (16)	0.0075 (17)
C2	0.062 (3)	0.049 (2)	0.057 (3)	0.028 (2)	0.019 (2)	0.0085 (19)
C3	0.053 (2)	0.049 (2)	0.063 (3)	0.0225 (18)	0.020 (2)	0.0208 (19)
C4	0.0401 (19)	0.047 (2)	0.0367 (19)	0.0181 (16)	0.0074 (15)	0.0088 (16)
C5	0.046 (2)	0.0353 (18)	0.0369 (19)	0.0133 (15)	0.0129 (15)	0.0119 (15)
C6	0.079 (3)	0.0369 (19)	0.038 (2)	0.0264 (19)	0.0231 (19)	0.0102 (16)
C7	0.108 (4)	0.050 (2)	0.041 (2)	0.037 (2)	0.024 (2)	0.0197 (19)
C8	0.102 (4)	0.043 (2)	0.052 (3)	0.037 (2)	0.024 (2)	0.0185 (19)
C9	0.084 (3)	0.044 (2)	0.049 (2)	0.034 (2)	0.025 (2)	0.0085 (18)
C10	0.061 (2)	0.047 (2)	0.0336 (19)	0.0197 (18)	0.0144 (17)	0.0056 (16)
C11	0.0413 (19)	0.0407 (19)	0.0367 (19)	0.0057 (15)	0.0104 (15)	0.0126 (15)
C12	0.041 (2)	0.083 (3)	0.051 (2)	0.023 (2)	0.0114 (18)	0.021 (2)
C13	0.052 (2)	0.086 (3)	0.052 (3)	0.028 (2)	0.022 (2)	0.015 (2)
C14	0.057 (2)	0.041 (2)	0.042 (2)	0.0040 (17)	0.0207 (18)	0.0107 (17)

Geometric parameters (Å, º) top

Br1—C1	1.857 (4)	C2—C3	1.404 (6)
Br2—C14	1.861 (4)	C2—H2	0.930
S1—C4	1.713 (4)	C3—C4	1.349 (5)
S1—C1	1.713 (4)	C3—H3	0.930
S2—O2	1.415 (3)	C5—C6	1.374 (5)
S2—O1	1.420 (3)	C5—C10	1.389 (5)
S2—N1	1.677 (3)	C6—C7	1.372 (5)
S2—C4	1.735 (4)	C6—H6	0.930
S3—O3	1.417 (3)	C7—C8	1.374 (6)
S3—O4	1.417 (3)	C8—C9	1.378 (6)
S3—N1	1.686 (3)	C8—H8	0.930
S3—C11	1.727 (4)	C9—C10	1.380 (5)
S4—C14	1.704 (4)	C9—H9	0.930
S4—C11	1.715 (4)	C10—H10	0.930
O5—N2	1.181 (5)	C11—C12	1.348 (5)
O6—N2	1.182 (5)	C12—C13	1.404 (6)
N1—C5	1.444 (4)	C12—H12	0.930
N2—C7	1.475 (6)	C13—C14	1.349 (6)
C1—C2	1.348 (6)	C13—H13	0.930

C4—S1—C1	89.88 (19)	S1—C4—S2	120.6 (2)
O2—S2—O1	120.68 (18)	C6—C5—C10	120.7 (3)
O2—S2—N1	107.56 (16)	C6—C5—N1	119.4 (3)
O1—S2—N1	104.87 (16)	C10—C5—N1	119.9 (3)
O2—S2—C4	109.33 (18)	C7—C6—C5	117.9 (3)
O1—S2—C4	107.98 (18)	C7—C6—H6	121.1
N1—S2—C4	105.36 (16)	C5—C6—H6	121.1
O3—S3—O4	121.60 (18)	C6—C7—C8	123.3 (4)
O3—S3—N1	105.18 (16)	C6—C7—N2	117.7 (4)
O4—S3—N1	106.70 (16)	C8—C7—N2	119.0 (4)
O3—S3—C11	107.58 (18)	C7—C8—C9	117.8 (4)
O4—S3—C11	110.68 (17)	C7—C8—H8	121.1
N1—S3—C11	103.50 (16)	C9—C8—H8	121.1
C14—S4—C11	90.14 (19)	C8—C9—C10	120.8 (3)
C5—N1—S2	118.8 (2)	C8—C9—H9	119.6
C5—N1—S3	118.3 (2)	C10—C9—H9	119.6
S2—N1—S3	122.91 (17)	C9—C10—C5	119.5 (4)
O5—N2—O6	121.7 (5)	C9—C10—H10	120.3
O5—N2—C7	119.4 (4)	C5—C10—H10	120.3
O6—N2—C7	118.9 (4)	C12—C11—S4	112.0 (3)
C2—C1—S1	112.9 (3)	C12—C11—S3	125.2 (3)
C2—C1—Br1	126.3 (3)	S4—C11—S3	122.5 (2)
S1—C1—Br1	120.7 (2)	C11—C12—C13	113.2 (4)
C1—C2—C3	112.2 (4)	C11—C12—H12	123.4
C1—C2—H2	123.9	C13—C12—H12	123.4
C3—C2—H2	123.9	C14—C13—C12	111.1 (4)
C4—C3—C2	112.0 (4)	C14—C13—H13	124.4
C4—C3—H3	124.0	C12—C13—H13	124.4
C2—C3—H3	124.0	C13—C14—S4	113.5 (3)
C3—C4—S1	113.0 (3)	C13—C14—Br2	126.8 (3)
C3—C4—S2	126.4 (3)	S4—C14—Br2	119.7 (2)

O2—S2—N1—C5	149.9 (3)	S3—N1—C5—C10	97.3 (4)
O1—S2—N1—C5	20.3 (3)	C10—C5—C6—C7	−0.1 (6)
C4—S2—N1—C5	−93.5 (3)	N1—C5—C6—C7	179.2 (4)
O2—S2—N1—S3	−30.6 (3)	C5—C6—C7—C8	0.2 (7)
O1—S2—N1—S3	−160.2 (2)	C5—C6—C7—N2	179.5 (5)
C4—S2—N1—S3	86.0 (2)	O5—N2—C7—C6	0.2 (9)
O3—S3—N1—C5	28.7 (3)	O6—N2—C7—C6	−178.8 (7)
O4—S3—N1—C5	159.1 (3)	O5—N2—C7—C8	179.5 (6)
C11—S3—N1—C5	−84.1 (3)	O6—N2—C7—C8	0.5 (10)
O3—S3—N1—S2	−150.8 (2)	C6—C7—C8—C9	−0.4 (8)
O4—S3—N1—S2	−20.4 (3)	N2—C7—C8—C9	−179.7 (5)
C11—S3—N1—S2	96.4 (2)	C7—C8—C9—C10	0.5 (7)
C4—S1—C1—C2	−0.3 (3)	C8—C9—C10—C5	−0.4 (7)
C4—S1—C1—Br1	−176.5 (2)	C6—C5—C10—C9	0.2 (6)
S1—C1—C2—C3	0.6 (5)	N1—C5—C10—C9	−179.1 (4)
Br1—C1—C2—C3	176.5 (3)	C14—S4—C11—C12	0.9 (3)
C1—C2—C3—C4	−0.6 (5)	C14—S4—C11—S3	174.4 (2)
C2—C3—C4—S1	0.3 (4)	O3—S3—C11—C12	−18.7 (4)
C2—C3—C4—S2	179.4 (3)	O4—S3—C11—C12	−153.7 (3)
C1—S1—C4—C3	0.0 (3)	N1—S3—C11—C12	92.3 (4)
C1—S1—C4—S2	−179.1 (2)	O3—S3—C11—S4	168.6 (2)
O2—S2—C4—C3	26.3 (4)	O4—S3—C11—S4	33.6 (3)
O1—S2—C4—C3	159.3 (3)	N1—S3—C11—S4	−80.4 (2)
N1—S2—C4—C3	−89.1 (4)	S4—C11—C12—C13	−0.9 (5)
O2—S2—C4—S1	−154.7 (2)	S3—C11—C12—C13	−174.2 (3)
O1—S2—C4—S1	−21.7 (3)	C11—C12—C13—C14	0.5 (6)
N1—S2—C4—S1	90.0 (2)	C12—C13—C14—S4	0.2 (5)
S2—N1—C5—C6	97.4 (4)	C12—C13—C14—Br2	177.6 (3)
S3—N1—C5—C6	−82.1 (4)	C11—S4—C14—C13	−0.6 (3)
S2—N1—C5—C10	−83.2 (4)	C11—S4—C14—Br2	−178.2 (2)

Experimental details

Crystal data
Chemical formula	C₁₄H₈Br₂N₂O₆S₄
M_r	588.30
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.5147 (7), 9.3674 (7), 13.7585 (11)
α, β, γ (°)	103.109 (1), 100.810 (1), 105.155 (1)
V (Å³)	995.42 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.53
Crystal size (mm)	0.29 × 0.26 × 0.21

Data collection
Diffractometer	Bruker APEX area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.294, 0.392
No. of measured, independent and observed [I > 2σ(I)] reflections	5264, 3451, 2895
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.095, 1.02
No. of reflections	3451
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.50

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002), SHELXL97.

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