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

In the crystal structure of the title compound (N4CPSTMAA), C(11)H(14)ClNO(3)S, the conformations of the N-H and C=O bonds in the amide group are anti to each other, similar to those observed in N-phenyl-sulfonyl-2,2,2-trimethyl-acetamide (NPSTMAA) and 2,2,2-trimethyl-N-(4-methyl-phenyl-sulfon-yl)acetamide (N4MPSTMAA). The bond parameters in N4CPSTMAA are similar to those in NPSTMAA, N4MPSTMAA, N-aryl-2,2,2-trimethyl-acetamides and 4-chloro-benzene-sulfonamide. The -SNHCOC- unit including the amide group is essentially planar and makes a dihedral angle of 82.2 (1)° with the benzene ring, comparable to the values of 79.1 (1) and 71.2 (1)° in NPSTMAA and N4MPSTMAA, respectively. The mol-ecules in N4CPSTMAA are linked into a chain by inter-molecular N-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C11H14ClNO3S

M = 275.74

Triclinic,

a = 6.034 (2) Å

b = 10.695 (2) Å

c = 11.134 (2) Å

α = 67.13 (2)°

β = 79.76 (2)°

γ = 88.46 (2)°

V = 650.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.45 mm−1

T = 299 (2) K

0.50 × 0.24 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (; Oxford Diffraction, 2007 ▶) T min = 0.806, T max = 0.948

7016 measured reflections

2595 independent reflections

1901 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.129

S = 1.10

2595 reflections

157 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.51 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/S1600536808017583/is2303sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017583/is2303Isup2.hkl

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

C11H14ClNO3S	Z = 2
Mr = 275.74	F000 = 288
Triclinic, P1	Dx = 1.407 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.034 (2) Å	Cell parameters from 2338 reflections
b = 10.695 (2) Å	θ = 2.3–27.9º
c = 11.134 (2) Å	µ = 0.45 mm−1
α = 67.13 (2)º	T = 299 (2) K
β = 79.76 (2)º	Long needle, colourless
γ = 88.46 (2)º	0.50 × 0.24 × 0.12 mm
V = 650.8 (3) Å3

Oxford Diffraction Xcalibur diffractometer	2595 independent reflections
Radiation source: fine-focus sealed tube	1901 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
T = 299(2) K	θmax = 26.4º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −6→7
Tmin = 0.807, Tmax = 0.948	k = −13→13
7016 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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.5579P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2595 reflections	Δρmax = 0.24 e Å−3
157 parameters	Δρmin = −0.51 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
C1	0.3219 (4)	0.2479 (2)	0.6007 (2)	0.0368 (5)
C2	0.2137 (4)	0.3650 (2)	0.5986 (2)	0.0407 (6)
H2	0.0845	0.3889	0.5615	0.049*
C3	0.3008 (5)	0.4452 (3)	0.6522 (3)	0.0477 (7)
H3	0.2315	0.5244	0.6509	0.057*
C4	0.4906 (5)	0.4074 (3)	0.7075 (3)	0.0471 (6)
C5	0.5980 (5)	0.2899 (3)	0.7113 (3)	0.0501 (7)
H5	0.7249	0.2650	0.7504	0.060*
C6	0.5129 (4)	0.2108 (3)	0.6559 (3)	0.0461 (6)
H6	0.5841	0.1326	0.6558	0.055*
C7	0.0583 (4)	−0.0409 (3)	0.7704 (2)	0.0394 (6)
C8	0.0948 (5)	−0.1803 (3)	0.8733 (2)	0.0438 (6)
C9	0.0658 (8)	−0.2896 (3)	0.8210 (4)	0.0875 (13)
H9A	0.1730	−0.2718	0.7408	0.105*
H9B	−0.0842	−0.2892	0.8032	0.105*
H9C	0.0903	−0.3768	0.8861	0.105*
C10	−0.0751 (6)	−0.2068 (4)	1.0003 (3)	0.0711 (10)
H10A	−0.2252	−0.2043	0.9821	0.085*
H10B	−0.0538	−0.1382	1.0333	0.085*
H10C	−0.0535	−0.2945	1.0654	0.085*
C11	0.3316 (6)	−0.1784 (4)	0.9012 (3)	0.0791 (11)
H11A	0.3474	−0.1092	0.9344	0.095*
H11B	0.4390	−0.1595	0.8209	0.095*
H11C	0.3583	−0.2652	0.9661	0.095*
N1	0.1921 (4)	−0.0075 (2)	0.6461 (2)	0.0408 (5)
H1N	0.291 (5)	−0.055 (3)	0.630 (3)	0.049*
O1	0.0027 (3)	0.1924 (2)	0.49806 (19)	0.0521 (5)
O2	0.3885 (4)	0.13680 (19)	0.42621 (17)	0.0554 (5)
O3	−0.0693 (3)	0.0397 (2)	0.79256 (19)	0.0574 (5)
Cl1	0.60248 (18)	0.50755 (8)	0.77505 (9)	0.0778 (3)
S1	0.21651 (11)	0.14675 (6)	0.52882 (6)	0.0413 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0414 (13)	0.0260 (11)	0.0349 (12)	0.0021 (10)	0.0005 (10)	−0.0064 (9)
C2	0.0457 (14)	0.0309 (12)	0.0413 (13)	0.0110 (10)	−0.0078 (11)	−0.0100 (10)
C3	0.0599 (17)	0.0277 (12)	0.0493 (15)	0.0075 (11)	−0.0035 (13)	−0.0115 (11)
C4	0.0610 (17)	0.0320 (12)	0.0430 (14)	−0.0069 (12)	−0.0048 (12)	−0.0102 (11)
C5	0.0442 (15)	0.0409 (14)	0.0579 (16)	0.0037 (12)	−0.0131 (13)	−0.0099 (12)
C6	0.0426 (14)	0.0328 (13)	0.0581 (16)	0.0096 (11)	−0.0066 (12)	−0.0144 (12)
C7	0.0418 (13)	0.0422 (13)	0.0349 (12)	0.0025 (11)	−0.0064 (10)	−0.0163 (11)
C8	0.0531 (15)	0.0386 (13)	0.0346 (12)	0.0026 (11)	−0.0068 (11)	−0.0092 (11)
C9	0.163 (4)	0.0344 (16)	0.061 (2)	−0.001 (2)	−0.026 (2)	−0.0127 (15)
C10	0.072 (2)	0.074 (2)	0.0448 (16)	0.0038 (18)	0.0027 (15)	−0.0050 (15)
C11	0.066 (2)	0.087 (3)	0.060 (2)	0.0057 (19)	−0.0204 (17)	0.0012 (18)
N1	0.0554 (13)	0.0292 (10)	0.0359 (11)	0.0087 (9)	−0.0031 (10)	−0.0133 (9)
O1	0.0609 (12)	0.0500 (11)	0.0493 (11)	0.0138 (9)	−0.0197 (9)	−0.0200 (9)
O2	0.0754 (13)	0.0433 (10)	0.0366 (9)	0.0141 (9)	0.0048 (9)	−0.0110 (8)
O3	0.0613 (12)	0.0543 (12)	0.0489 (11)	0.0205 (10)	0.0008 (9)	−0.0175 (9)
Cl1	0.1118 (8)	0.0485 (5)	0.0812 (6)	−0.0064 (4)	−0.0330 (5)	−0.0266 (4)
S1	0.0536 (4)	0.0328 (3)	0.0340 (3)	0.0090 (3)	−0.0047 (3)	−0.0110 (2)

C1—C6	1.378 (4)	C8—C9	1.520 (4)
C1—C2	1.391 (3)	C8—C10	1.523 (4)
C1—S1	1.763 (3)	C9—H9A	0.9600
C2—C3	1.380 (4)	C9—H9B	0.9600
C2—H2	0.9300	C9—H9C	0.9600
C3—C4	1.374 (4)	C10—H10A	0.9600
C3—H3	0.9300	C10—H10B	0.9600
C4—C5	1.387 (4)	C10—H10C	0.9600
C4—Cl1	1.736 (3)	C11—H11A	0.9600
C5—C6	1.379 (4)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C6—H6	0.9300	N1—S1	1.649 (2)
C7—O3	1.208 (3)	N1—H1N	0.82 (3)
C7—N1	1.389 (3)	O1—S1	1.419 (2)
C7—C8	1.525 (3)	O2—S1	1.4354 (19)
C8—C11	1.518 (4)
C6—C1—C2	121.1 (2)	C8—C9—H9A	109.5
C6—C1—S1	119.36 (19)	C8—C9—H9B	109.5
C2—C1—S1	119.5 (2)	H9A—C9—H9B	109.5
C3—C2—C1	119.0 (2)	C8—C9—H9C	109.5
C3—C2—H2	120.5	H9A—C9—H9C	109.5
C1—C2—H2	120.5	H9B—C9—H9C	109.5
C4—C3—C2	119.5 (2)	C8—C10—H10A	109.5
C4—C3—H3	120.2	C8—C10—H10B	109.5
C2—C3—H3	120.2	H10A—C10—H10B	109.5
C3—C4—C5	121.7 (3)	C8—C10—H10C	109.5
C3—C4—Cl1	120.0 (2)	H10A—C10—H10C	109.5
C5—C4—Cl1	118.2 (2)	H10B—C10—H10C	109.5
C6—C5—C4	118.7 (3)	C8—C11—H11A	109.5
C6—C5—H5	120.6	C8—C11—H11B	109.5
C4—C5—H5	120.6	H11A—C11—H11B	109.5
C1—C6—C5	119.8 (2)	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
O3—C7—N1	120.3 (2)	C7—N1—S1	123.41 (18)
O3—C7—C8	124.5 (2)	C7—N1—H1N	123 (2)
N1—C7—C8	115.1 (2)	S1—N1—H1N	112 (2)
C11—C8—C9	110.4 (3)	O1—S1—O2	118.95 (12)
C11—C8—C10	109.3 (3)	O1—S1—N1	110.80 (12)
C9—C8—C10	110.1 (3)	O2—S1—N1	103.81 (11)
C11—C8—C7	108.0 (2)	O1—S1—C1	108.91 (12)
C9—C8—C7	110.1 (2)	O2—S1—C1	109.30 (12)
C10—C8—C7	109.0 (2)	N1—S1—C1	103.99 (11)
C6—C1—C2—C3	0.3 (4)	O3—C7—C8—C10	7.1 (4)
S1—C1—C2—C3	−178.41 (19)	N1—C7—C8—C10	−175.6 (2)
C1—C2—C3—C4	−0.6 (4)	O3—C7—N1—S1	9.2 (4)
C2—C3—C4—C5	−0.1 (4)	C8—C7—N1—S1	−168.17 (19)
C2—C3—C4—Cl1	179.8 (2)	C7—N1—S1—O1	−57.7 (2)
C3—C4—C5—C6	1.0 (4)	C7—N1—S1—O2	173.5 (2)
Cl1—C4—C5—C6	−178.9 (2)	C7—N1—S1—C1	59.2 (2)
C2—C1—C6—C5	0.6 (4)	C6—C1—S1—O1	170.94 (19)
S1—C1—C6—C5	179.4 (2)	C2—C1—S1—O1	−10.3 (2)
C4—C5—C6—C1	−1.3 (4)	C6—C1—S1—O2	−57.6 (2)
O3—C7—C8—C11	−111.5 (3)	C2—C1—S1—O2	121.2 (2)
N1—C7—C8—C11	65.7 (3)	C6—C1—S1—N1	52.8 (2)
O3—C7—C8—C9	127.9 (3)	C2—C1—S1—N1	−128.5 (2)
N1—C7—C8—C9	−54.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.82 (3)	2.19 (3)	2.986 (3)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.82 (3)	2.19 (3)	2.986 (3)	165 (3)

Symmetry code: (i) .