N-[4-(Azetidin-1-ylsulfon-yl)phen-yl]-N-(2,4-difluoro-benz-yl)acetamide.

In the title mol-ecule, C(18)H(18)F(2)N(2)O(3)S, the dihedral angle between the benzene rings is 79.40 (11)°. The 2,4-difluoro-benzyl and azetidine fragments adopt a trans arrangement relative to the central benzene ring. In the crystal, weak C-H⋯O hydrogen bonds connect mol-ecules into a two-dimensional network parallel to (001).

Related literature

For the pharmacological activity of sulfonamides, see: Song et al. (2007 ▶); Wang, Wang et al. (2010 ▶); Wang, Wan & Zhou (2010 ▶); Wang, Gan et al. (2010 ▶).

Experimental

Crystal data

C18H18F2N2O3S

M = 380.40

Monoclinic,

a = 8.7793 (15) Å

b = 8.4442 (15) Å

c = 23.810 (4) Å

β = 97.312 (6)°

V = 1750.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.22 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.000, T max = 0.001

14668 measured reflections

3077 independent reflections

2684 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.143

S = 1.04

3077 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038342/lh5527sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038342/lh5527Isup2.hkl

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

C18H18F2N2O3S	F(000) = 792
Mr = 380.40	Dx = 1.443 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2005 reflections
a = 8.7793 (15) Å	θ = 1.3–25.0°
b = 8.4442 (15) Å	µ = 0.23 mm−1
c = 23.810 (4) Å	T = 293 K
β = 97.312 (6)°	Plate, colourless
V = 1750.8 (5) Å3	0.22 × 0.21 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	3077 independent reflections
Radiation source: fine-focus sealed tube	2684 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.000, Tmax = 0.001	k = −9→10
14668 measured reflections	l = −25→28

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.0875P)2 + 0.736P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3077 reflections	Δρmax = 0.34 e Å−3
236 parameters	Δρmin = −0.38 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (2)

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	0.6694 (2)	0.5645 (3)	0.33594 (10)	0.0447 (5)
C6	0.5341 (2)	0.5834 (2)	0.35904 (9)	0.0365 (5)
C5	0.4212 (3)	0.6715 (3)	0.32755 (10)	0.0490 (6)
H3	0.3291	0.6899	0.3419	0.059*
C4	0.4418 (3)	0.7332 (3)	0.27524 (11)	0.0597 (7)
H4	0.3647	0.7921	0.2544	0.072*
C3	0.5781 (3)	0.7056 (3)	0.25474 (11)	0.0585 (7)
C2	0.6955 (3)	0.6231 (3)	0.28413 (12)	0.0580 (7)
H6	0.7883	0.6073	0.2700	0.070*
C13	0.1006 (2)	0.1070 (3)	0.36580 (9)	0.0385 (5)
C12	0.2177 (3)	0.0895 (3)	0.41033 (10)	0.0432 (5)
H8	0.2401	−0.0099	0.4261	0.052*
C11	0.3003 (2)	0.2199 (3)	0.43111 (9)	0.0403 (5)
H9	0.3793	0.2088	0.4608	0.048*
C10	0.2657 (2)	0.3687 (2)	0.40761 (8)	0.0340 (5)
C14	0.0659 (2)	0.2550 (3)	0.34245 (9)	0.0416 (5)
H11	−0.0129	0.2661	0.3127	0.050*
C15	0.1482 (2)	0.3860 (3)	0.36341 (10)	0.0408 (5)
H12	0.1249	0.4855	0.3479	0.049*
C16	−0.2870 (3)	0.0478 (3)	0.36281 (14)	0.0658 (8)
H13A	−0.3687	0.0261	0.3324	0.079*
H13B	−0.2526	0.1567	0.3616	0.079*
C8	0.3049 (2)	0.6238 (2)	0.45767 (9)	0.0370 (5)
C9	0.1495 (3)	0.6048 (3)	0.47658 (11)	0.0512 (6)
H15A	0.1050	0.5065	0.4625	0.077*
H15B	0.0846	0.6909	0.4621	0.077*
H15C	0.1594	0.6050	0.5172	0.077*
C7	0.5160 (2)	0.5089 (3)	0.41508 (9)	0.0401 (5)
H7A	0.5562	0.4019	0.4155	0.048*
H7B	0.5774	0.5679	0.4448	0.048*
C18	−0.1690 (3)	−0.0912 (4)	0.42815 (12)	0.0616 (7)
H17A	−0.0888	−0.0364	0.4524	0.074*
H17B	−0.1762	−0.2011	0.4394	0.074*
C17	−0.3228 (3)	−0.0043 (4)	0.42063 (14)	0.0686 (8)
H18A	−0.4113	−0.0735	0.4195	0.082*
H18B	−0.3289	0.0821	0.4471	0.082*
N1	−0.1609 (2)	−0.0694 (2)	0.36736 (9)	0.0457 (5)
N2	0.35756 (18)	0.5030 (2)	0.42793 (7)	0.0351 (4)
O1	0.38424 (18)	0.74030 (19)	0.47069 (7)	0.0496 (4)
O2	−0.0512 (3)	−0.0306 (2)	0.27960 (8)	0.0689 (6)
O3	0.08117 (19)	−0.19746 (19)	0.35635 (9)	0.0595 (5)
F1	0.5958 (3)	0.7614 (3)	0.20283 (8)	0.0956 (7)
F2	0.78369 (17)	0.4820 (2)	0.36687 (8)	0.0728 (5)
S2	−0.00544 (6)	−0.05936 (7)	0.33804 (2)	0.0439 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0383 (11)	0.0416 (13)	0.0557 (14)	−0.0018 (9)	0.0115 (10)	−0.0043 (10)
C6	0.0371 (10)	0.0311 (10)	0.0421 (11)	−0.0042 (8)	0.0083 (9)	−0.0032 (8)
C5	0.0438 (12)	0.0515 (14)	0.0535 (14)	0.0057 (10)	0.0137 (10)	0.0076 (11)
C4	0.0662 (16)	0.0605 (16)	0.0530 (14)	0.0034 (13)	0.0103 (12)	0.0172 (12)
C3	0.0729 (17)	0.0577 (16)	0.0481 (14)	−0.0133 (13)	0.0197 (12)	0.0055 (12)
C2	0.0581 (14)	0.0542 (15)	0.0678 (17)	−0.0120 (12)	0.0321 (13)	−0.0068 (13)
C13	0.0394 (11)	0.0356 (11)	0.0408 (11)	−0.0024 (9)	0.0056 (9)	−0.0033 (9)
C12	0.0475 (12)	0.0318 (11)	0.0494 (13)	0.0023 (9)	0.0024 (10)	0.0060 (9)
C11	0.0396 (10)	0.0384 (12)	0.0411 (11)	0.0002 (9)	−0.0021 (9)	0.0051 (9)
C10	0.0327 (10)	0.0326 (11)	0.0373 (10)	−0.0003 (8)	0.0074 (8)	0.0001 (8)
C14	0.0404 (11)	0.0413 (12)	0.0412 (11)	0.0013 (9)	−0.0021 (9)	0.0025 (9)
C15	0.0404 (11)	0.0346 (11)	0.0463 (12)	0.0024 (9)	0.0013 (9)	0.0055 (9)
C16	0.0453 (13)	0.0574 (17)	0.092 (2)	0.0090 (12)	0.0002 (14)	0.0004 (14)
C8	0.0399 (11)	0.0355 (12)	0.0352 (10)	0.0009 (9)	0.0029 (8)	0.0033 (9)
C9	0.0464 (12)	0.0544 (14)	0.0551 (14)	0.0036 (11)	0.0156 (11)	−0.0045 (11)
C7	0.0310 (10)	0.0428 (12)	0.0466 (12)	0.0017 (8)	0.0056 (9)	0.0045 (9)
C18	0.0587 (15)	0.0660 (17)	0.0618 (16)	0.0032 (13)	0.0146 (13)	0.0028 (13)
C17	0.0558 (15)	0.0649 (18)	0.088 (2)	0.0014 (13)	0.0218 (15)	−0.0165 (16)
N1	0.0413 (10)	0.0402 (11)	0.0541 (12)	−0.0020 (8)	0.0009 (9)	−0.0068 (8)
N2	0.0316 (8)	0.0346 (9)	0.0395 (9)	−0.0028 (7)	0.0068 (7)	0.0008 (7)
O1	0.0548 (9)	0.0397 (9)	0.0534 (10)	−0.0071 (7)	0.0036 (8)	−0.0062 (7)
O2	0.0911 (14)	0.0710 (13)	0.0438 (10)	−0.0216 (11)	0.0058 (9)	−0.0158 (9)
O3	0.0549 (10)	0.0342 (9)	0.0909 (14)	0.0033 (7)	0.0156 (9)	−0.0119 (9)
F1	0.1171 (15)	0.1121 (16)	0.0652 (11)	−0.0096 (12)	0.0409 (11)	0.0288 (10)
F2	0.0422 (8)	0.0833 (12)	0.0961 (13)	0.0171 (8)	0.0213 (8)	0.0172 (9)
S2	0.0484 (4)	0.0368 (4)	0.0468 (4)	−0.0036 (2)	0.0076 (3)	−0.0109 (2)

C1—F2	1.359 (3)	C15—H12	0.9300
C1—C2	1.375 (4)	C16—N1	1.479 (3)
C1—C6	1.381 (3)	C16—C17	1.516 (5)
C6—C5	1.382 (3)	C16—H13A	0.9700
C6—C7	1.502 (3)	C16—H13B	0.9700
C5—C4	1.383 (4)	C8—O1	1.223 (3)
C5—H3	0.9300	C8—N2	1.356 (3)
C4—C3	1.369 (4)	C8—C9	1.499 (3)
C4—H4	0.9300	C9—H15A	0.9600
C3—F1	1.350 (3)	C9—H15B	0.9600
C3—C2	1.362 (4)	C9—H15C	0.9600
C2—H6	0.9300	C7—N2	1.463 (3)
C13—C14	1.386 (3)	C7—H7A	0.9700
C13—C12	1.388 (3)	C7—H7B	0.9700
C13—S2	1.766 (2)	C18—N1	1.470 (3)
C12—C11	1.376 (3)	C18—C17	1.527 (4)
C12—H8	0.9300	C18—H17A	0.9700
C11—C10	1.393 (3)	C18—H17B	0.9700
C11—H9	0.9300	C17—H18A	0.9700
C10—C15	1.384 (3)	C17—H18B	0.9700
C10—N2	1.439 (3)	N1—S2	1.612 (2)
C14—C15	1.380 (3)	O2—S2	1.419 (2)
C14—H11	0.9300	O3—S2	1.4296 (18)
F2—C1—C2	118.4 (2)	H13A—C16—H13B	111.1
F2—C1—C6	117.2 (2)	O1—C8—N2	121.09 (19)
C2—C1—C6	124.5 (2)	O1—C8—C9	121.4 (2)
C1—C6—C5	116.1 (2)	N2—C8—C9	117.43 (19)
C1—C6—C7	119.94 (19)	C8—C9—H15A	109.5
C5—C6—C7	123.92 (19)	C8—C9—H15B	109.5
C6—C5—C4	121.6 (2)	H15A—C9—H15B	109.5
C6—C5—H3	119.2	C8—C9—H15C	109.5
C4—C5—H3	119.2	H15A—C9—H15C	109.5
C3—C4—C5	118.5 (2)	H15B—C9—H15C	109.5
C3—C4—H4	120.7	N2—C7—C6	114.27 (17)
C5—C4—H4	120.7	N2—C7—H7A	108.7
F1—C3—C2	118.8 (2)	C6—C7—H7A	108.7
F1—C3—C4	118.3 (3)	N2—C7—H7B	108.7
C2—C3—C4	122.9 (2)	C6—C7—H7B	108.7
C3—C2—C1	116.3 (2)	H7A—C7—H7B	107.6
C3—C2—H6	121.8	N1—C18—C17	88.7 (2)
C1—C2—H6	121.8	N1—C18—H17A	113.9
C14—C13—C12	120.43 (19)	C17—C18—H17A	113.9
C14—C13—S2	119.25 (16)	N1—C18—H17B	113.9
C12—C13—S2	120.32 (17)	C17—C18—H17B	113.9
C11—C12—C13	119.6 (2)	H17A—C18—H17B	111.1
C11—C12—H8	120.2	C16—C17—C18	87.9 (2)
C13—C12—H8	120.2	C16—C17—H18A	114.0
C12—C11—C10	119.96 (19)	C18—C17—H18A	114.0
C12—C11—H9	120.0	C16—C17—H18B	114.0
C10—C11—H9	120.0	C18—C17—H18B	114.0
C15—C10—C11	120.28 (19)	H18A—C17—H18B	111.2
C15—C10—N2	120.25 (18)	C18—N1—C16	91.5 (2)
C11—C10—N2	119.41 (17)	C18—N1—S2	125.64 (16)
C15—C14—C13	119.97 (19)	C16—N1—S2	126.87 (18)
C15—C14—H11	120.0	C8—N2—C10	123.67 (16)
C13—C14—H11	120.0	C8—N2—C7	118.69 (17)
C14—C15—C10	119.72 (19)	C10—N2—C7	117.64 (17)
C14—C15—H12	120.1	O2—S2—O3	120.79 (12)
C10—C15—H12	120.1	O2—S2—N1	106.48 (12)
N1—C16—C17	88.8 (2)	O3—S2—N1	105.75 (11)
N1—C16—H13A	113.8	O2—S2—C13	107.50 (11)
C17—C16—H13A	113.8	O3—S2—C13	107.47 (10)
N1—C16—H13B	113.8	N1—S2—C13	108.35 (10)
C17—C16—H13B	113.8

D—H···A	D—H	H···A	D···A	D—H···A
C5—H3···O3i	0.93	2.44	3.336 (3)	162
C11—H9···O1ii	0.93	2.51	3.406 (3)	162
C17—H18B···O1iii	0.97	2.56	3.509 (4)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H3⋯O3i	0.93	2.44	3.336 (3)	162
C11—H9⋯O1ii	0.93	2.51	3.406 (3)	162
C17—H18B⋯O1iii	0.97	2.56	3.509 (4)	166

Symmetry codes: (i) ; (ii) ; (iii) .