N-(4-Bromo-phenyl-sulfon-yl)-2,2,2-tri-methyl-acetamide.

The conformations of the N-H and C=O bonds in the SO(2)-NH-CO-C group of the title compound (N4BPSTMAA), C(11)H(14)BrNO(3)S, are trans to each other, similar to what is observed in N-(4-chloro-phenyl-sulfon-yl)-2,2,2-trimethyl-acet-amide (N4CPSTMAA) and 2,2,2-trimethyl-N-(4-methyl-phenyl--sulfon-yl)acetamide (N4MPSTMAA). The bond para-meters in N4BPSTMAA are similar to those in N4CPSTMAA, N4MPSTMAA, N-aryl-2,2,2-trimethyl-acet-amides and 4-bromo-benzene-sulfonamide. The benzene ring and the SO(2)-NH-CO-C group in N4BPSTMAA form a dihedral angle of 82.8 (1)°, comparable with the values of 82.2 (1)° in N4CPSTMAA and 71.2 (1)° in N4MPSTMAA. N-H⋯O hydrogen bonds form a centrosymmetric ring characterized by an R(2) (2)(8) motif.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2007 ▶, 2008 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H14BrNO3S

M = 320.20

Triclinic,

a = 6.066 (1) Å

b = 10.858 (1) Å

c = 11.092 (2) Å

α = 68.19 (1)°

β = 78.66 (2)°

γ = 88.10 (2)°

V = 664.40 (17) Å3

Z = 2

Mo Kα radiation

μ = 3.25 mm−1

T = 299 (2) K

0.20 × 0.08 × 0.04 mm

Data collection

Oxford Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.563, T max = 0.881

6843 measured reflections

2692 independent reflections

1551 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 0.97

2692 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019375/bx2154sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019375/bx2154Isup2.hkl

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

C11H14BrNO3S	Z = 2
Mr = 320.20	F000 = 324
Triclinic, P1	Dx = 1.601 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.066 (1) Å	Cell parameters from 2537 reflections
b = 10.858 (1) Å	θ = 2.3–28.0º
c = 11.092 (2) Å	µ = 3.25 mm−1
α = 68.19 (1)º	T = 299 (2) K
β = 78.66 (2)º	Needle, colourless
γ = 88.10 (2)º	0.20 × 0.08 × 0.04 mm
V = 664.40 (17) Å3

Oxford Xcalibur diffractometer with Sapphire CCD detector	2692 independent reflections
Radiation source: fine-focus sealed tube	1551 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 299(2) K	θmax = 26.4º
Rotation method data acquisition using ω and φ scans	θmin = 2.3º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007) (Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm)	h = −7→7
Tmin = 0.563, Tmax = 0.881	k = −13→13
6843 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0526P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
2692 reflections	Δρmax = 0.37 e Å−3
154 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Br1	−0.10728 (8)	−0.00925 (4)	0.21716 (5)	0.0810 (2)
S1	0.28409 (14)	0.35519 (8)	0.47093 (8)	0.0451 (2)
O1	0.4965 (4)	0.3098 (2)	0.5007 (2)	0.0548 (6)
O2	0.1120 (4)	0.3668 (2)	0.5741 (2)	0.0580 (6)
O3	0.5763 (4)	0.4572 (2)	0.2073 (2)	0.0615 (7)
N1	0.3085 (4)	0.5038 (2)	0.3551 (3)	0.0449 (7)
H1N	0.2309	0.5653	0.3720	0.054*
C1	0.1807 (5)	0.2548 (3)	0.3993 (3)	0.0399 (8)
C2	0.2864 (6)	0.1387 (3)	0.4005 (3)	0.0478 (8)
H2	0.4134	0.1145	0.4378	0.057*
C3	0.2013 (6)	0.0601 (3)	0.3458 (3)	0.0513 (9)
H3	0.2703	−0.0176	0.3456	0.062*
C4	0.0124 (6)	0.0983 (3)	0.2914 (3)	0.0487 (9)
C5	−0.0926 (6)	0.2124 (3)	0.2896 (4)	0.0521 (9)
H5	−0.2193	0.2364	0.2520	0.062*
C6	−0.0080 (5)	0.2915 (3)	0.3443 (4)	0.0506 (9)
H6	−0.0778	0.3691	0.3440	0.061*
C7	0.4476 (6)	0.5366 (3)	0.2305 (3)	0.0428 (8)
C8	0.4154 (5)	0.6724 (3)	0.1284 (3)	0.0451 (8)
C9	0.1793 (6)	0.6700 (4)	0.0986 (4)	0.0740 (12)
H9A	0.1665	0.6008	0.0657	0.089*
H9B	0.1552	0.7540	0.0331	0.089*
H9C	0.0686	0.6536	0.1782	0.089*
C10	0.4365 (8)	0.7799 (4)	0.1826 (4)	0.0856 (14)
H10A	0.3232	0.7639	0.2611	0.103*
H10B	0.4169	0.8649	0.1172	0.103*
H10C	0.5828	0.7788	0.2037	0.103*
C11	0.5872 (7)	0.6969 (4)	0.0018 (4)	0.0759 (12)
H11A	0.7360	0.6951	0.0197	0.091*
H11B	0.5660	0.7821	−0.0628	0.091*
H11C	0.5684	0.6290	−0.0318	0.091*

	U11	U22	U33	U12	U13	U23
Br1	0.1133 (4)	0.0498 (3)	0.0888 (4)	−0.0078 (2)	−0.0360 (3)	−0.0269 (2)
S1	0.0570 (6)	0.0369 (5)	0.0389 (5)	0.0063 (4)	−0.0065 (4)	−0.0130 (4)
O1	0.0597 (15)	0.0513 (14)	0.0543 (15)	0.0087 (12)	−0.0183 (13)	−0.0177 (12)
O2	0.0759 (16)	0.0479 (14)	0.0402 (14)	0.0118 (12)	0.0055 (13)	−0.0145 (11)
O3	0.0650 (16)	0.0606 (16)	0.0540 (16)	0.0187 (14)	−0.0034 (13)	−0.0213 (13)
N1	0.0600 (17)	0.0323 (14)	0.0429 (17)	0.0063 (13)	−0.0063 (14)	−0.0169 (13)
C1	0.0397 (18)	0.0325 (17)	0.0390 (18)	−0.0038 (14)	0.0030 (15)	−0.0084 (14)
C2	0.051 (2)	0.0410 (19)	0.051 (2)	0.0136 (16)	−0.0139 (17)	−0.0153 (16)
C3	0.065 (2)	0.0285 (17)	0.054 (2)	0.0035 (16)	−0.0028 (19)	−0.0118 (16)
C4	0.060 (2)	0.0319 (17)	0.052 (2)	0.0014 (16)	−0.0134 (19)	−0.0121 (16)
C5	0.0446 (19)	0.042 (2)	0.059 (2)	−0.0033 (16)	−0.0081 (17)	−0.0081 (17)
C6	0.048 (2)	0.0362 (18)	0.065 (2)	0.0086 (16)	−0.0116 (19)	−0.0167 (17)
C7	0.045 (2)	0.049 (2)	0.0371 (19)	−0.0025 (17)	−0.0069 (16)	−0.0188 (16)
C8	0.048 (2)	0.0432 (19)	0.0356 (19)	−0.0061 (15)	−0.0020 (16)	−0.0076 (15)
C9	0.063 (3)	0.076 (3)	0.065 (3)	0.001 (2)	−0.021 (2)	−0.002 (2)
C10	0.144 (4)	0.041 (2)	0.070 (3)	−0.005 (2)	−0.029 (3)	−0.016 (2)
C11	0.071 (3)	0.077 (3)	0.057 (3)	−0.001 (2)	0.001 (2)	−0.006 (2)

Br1—C4	1.891 (3)	C5—H5	0.9300
S1—O1	1.420 (2)	C6—H6	0.9300
S1—O2	1.430 (2)	C7—C8	1.524 (5)
S1—N1	1.636 (3)	C8—C11	1.514 (5)
S1—C1	1.760 (3)	C8—C10	1.517 (5)
O3—C7	1.208 (4)	C8—C9	1.535 (5)
N1—C7	1.394 (4)	C9—H9A	0.9600
N1—H1N	0.8600	C9—H9B	0.9600
C1—C6	1.380 (4)	C9—H9C	0.9600
C1—C2	1.392 (4)	C10—H10A	0.9600
C2—C3	1.378 (4)	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C3—C4	1.380 (5)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—C5	1.369 (4)	C11—H11C	0.9600
C5—C6	1.381 (4)
O1—S1—O2	118.80 (15)	O3—C7—N1	120.2 (3)
O1—S1—N1	111.33 (14)	O3—C7—C8	124.0 (3)
O2—S1—N1	103.71 (14)	N1—C7—C8	115.7 (3)
O1—S1—C1	108.67 (15)	C11—C8—C10	110.9 (3)
O2—S1—C1	109.40 (15)	C11—C8—C7	109.5 (3)
N1—S1—C1	103.87 (14)	C10—C8—C7	110.3 (3)
C7—N1—S1	123.8 (2)	C11—C8—C9	108.6 (3)
C7—N1—H1N	118.1	C10—C8—C9	110.0 (3)
S1—N1—H1N	118.1	C7—C8—C9	107.6 (3)
C6—C1—C2	120.7 (3)	C8—C9—H9A	109.5
C6—C1—S1	119.2 (2)	C8—C9—H9B	109.5
C2—C1—S1	120.1 (2)	H9A—C9—H9B	109.5
C3—C2—C1	119.4 (3)	C8—C9—H9C	109.5
C3—C2—H2	120.3	H9A—C9—H9C	109.5
C1—C2—H2	120.3	H9B—C9—H9C	109.5
C2—C3—C4	119.1 (3)	C8—C10—H10A	109.5
C2—C3—H3	120.5	C8—C10—H10B	109.5
C4—C3—H3	120.5	H10A—C10—H10B	109.5
C5—C4—C3	122.0 (3)	C8—C10—H10C	109.5
C5—C4—Br1	118.6 (3)	H10A—C10—H10C	109.5
C3—C4—Br1	119.5 (2)	H10B—C10—H10C	109.5
C4—C5—C6	119.2 (3)	C8—C11—H11A	109.5
C4—C5—H5	120.4	C8—C11—H11B	109.5
C6—C5—H5	120.4	H11A—C11—H11B	109.5
C1—C6—C5	119.7 (3)	C8—C11—H11C	109.5
C1—C6—H6	120.1	H11A—C11—H11C	109.5
C5—C6—H6	120.1	H11B—C11—H11C	109.5
O1—S1—N1—C7	55.9 (3)	C3—C4—C5—C6	−0.3 (5)
O2—S1—N1—C7	−175.2 (2)	Br1—C4—C5—C6	179.6 (3)
C1—S1—N1—C7	−60.9 (3)	C2—C1—C6—C5	−0.1 (5)
O1—S1—C1—C6	−170.6 (3)	S1—C1—C6—C5	−179.0 (3)
O2—S1—C1—C6	58.2 (3)	C4—C5—C6—C1	0.2 (5)
N1—S1—C1—C6	−52.0 (3)	S1—N1—C7—O3	−7.6 (4)
O1—S1—C1—C2	10.5 (3)	S1—N1—C7—C8	169.3 (2)
O2—S1—C1—C2	−120.7 (3)	O3—C7—C8—C11	−6.7 (4)
N1—S1—C1—C2	129.1 (3)	N1—C7—C8—C11	176.5 (3)
C6—C1—C2—C3	0.1 (5)	O3—C7—C8—C10	−129.0 (4)
S1—C1—C2—C3	179.0 (3)	N1—C7—C8—C10	54.2 (4)
C1—C2—C3—C4	−0.2 (5)	O3—C7—C8—C9	111.0 (4)
C2—C3—C4—C5	0.3 (5)	N1—C7—C8—C9	−65.7 (4)
C2—C3—C4—Br1	−179.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86	2.23	2.982 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	2.23	2.982 (3)	146

Symmetry code: (i) .