organic compounds
N-[4-(Azetidin-1-ylsulfonyl)phenyl]-N-(2,4-difluorobenzyl)acetamide
aSichuan Provincial People's Hospital, Chengdu 610072, People's Republic of China, bLaboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China, and cSchool of Chemistry and Chemical Engineering, Bijie University, Bijie, Guizhou 551700, People's Republic of China
*Correspondence e-mail: ljs1234@swu.edu.cn
In the title molecule, C18H18F2N2O3S, the dihedral angle between the benzene rings is 79.40 (11)°. The 2,4-difluorobenzyl and azetidine fragments adopt a trans arrangement relative to the central benzene ring. In the crystal, weak C—H⋯O hydrogen bonds connect molecules into a two-dimensional network parallel to (001).
Related literature
For the pharmacological activity of et al. (2007); Wang, Wang et al. (2010); Wang, Wan & Zhou (2010); Wang, Gan et al. (2010).
see: SongExperimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell 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.
Supporting information
https://doi.org/10.1107/S1600536812038342/lh5527sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038342/lh5527Isup2.hkl
A suspension of N-(4-(azetidin-1-ylsulfonyl)phenyl)acetamide (0.8 g, 3.0 mmol) and potassium carbonate (0.5 g, 3.6 mmol) was stirred in acetonitrile (30 mL) at 343 K. After half an hour, 1-(bromomethyl)-2,4-difluorobenzene (0.6 g, 3.0 mmol) was added, and the progress of the reaction was monitored by TLC. Upon completion, the reaction was extracted with chloroform (3 × 20 mL). The filtrate was concentrated and then directly purified by chromatographic column (petroleum ether/ethyl acetate) to afford the title compound (I). A crystal suitable for X-ray analysis was grown from a solution of (I) in a mixture of acetone and ethyl acetate by slow evaporation at room temperature.
H atoms were placed at calculated position with C—H = 0.93 Å (aromatic), 0.97Å (methylene) 0.96 Å (methyl). The Uiso(H) value was set equal to 1.2Ueq(C) or 1.5Ueq(Cmethyl).
Sulfonamides were extensively employed as effective antimicrobial agents for the prevention and cure of bacterial infections in humanbiological systems as early as 70 years ago, and recently have aroused considerable interest in biology and medicine for their diversified pharmacological activities including antibacterial, antifungal, antiviral, antitumor, anti-inflammatory and as carbonic anhydrase inhibitors (Song, et al., 2007; Wang, Wang et al., 2010). Our interest is to develop novel sulfonamide derivatives as antimicrobial agents and some structrally related
have been reported as bioactive agents (Wang, Wan & Zhou, 2010; Wang & Gan et al., 2010). Herein, we report the of the title compound (I).In the molecule of (I) (Fig. 1) the dihedral angle between the two benzene rings is 79.40 (11)°. The 2,4-difluorobenzyl and azetidine fragments adopt a trans arrangement relative to the central benzene ring. In the crystal, weak C—H···O hydrogen bonds connect molecules into a two-dimensional network (Fig. 2) parallel to (001).
For the pharmacological activity of
see: Song et al. (2007); Wang, Wang et al. (2010); Wang, Wan et al. (2010); Wang, Gan et al. (2010).Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).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) |
C18H18F2N2O3S | V = 1750.8 (5) Å3 |
Mr = 380.40 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.7793 (15) Å | µ = 0.23 mm−1 |
b = 8.4442 (15) Å | T = 293 K |
c = 23.810 (4) Å | 0.22 × 0.21 × 0.20 mm |
β = 97.312 (6)° |
Bruker SMART CCD diffractometer | 3077 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2684 reflections with I > 2σ(I) |
Tmin = 0.000, Tmax = 0.001 | Rint = 0.036 |
14668 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.34 e Å−3 |
3077 reflections | Δρmin = −0.38 e Å−3 |
236 parameters |
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 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C18H18F2N2O3S |
Mr | 380.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 8.7793 (15), 8.4442 (15), 23.810 (4) |
β (°) | 97.312 (6) |
V (Å3) | 1750.8 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.22 × 0.21 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.000, 0.001 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14668, 3077, 2684 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.143, 1.04 |
No. of reflections | 3077 |
No. of parameters | 236 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.38 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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) x, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1. |
Acknowledgements
This work was partially supported by the Specialized Research Fund for the Doctoral Program of Higher Education of China (SRFDP20110182110007), the Research Funds for the Central Universities (XDJK2012B026) and the National Innovative Training Program for College Students.
References
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Sulfonamides were extensively employed as effective antimicrobial agents for the prevention and cure of bacterial infections in humanbiological systems as early as 70 years ago, and recently have aroused considerable interest in biology and medicine for their diversified pharmacological activities including antibacterial, antifungal, antiviral, antitumor, anti-inflammatory and as carbonic anhydrase inhibitors (Song, et al., 2007; Wang, Wang et al., 2010). Our interest is to develop novel sulfonamide derivatives as antimicrobial agents and some structrally related sulfonamides have been reported as bioactive agents (Wang, Wan & Zhou, 2010; Wang & Gan et al., 2010). Herein, we report the crystal structure of the title compound (I).
In the molecule of (I) (Fig. 1) the dihedral angle between the two benzene rings is 79.40 (11)°. The 2,4-difluorobenzyl and azetidine fragments adopt a trans arrangement relative to the central benzene ring. In the crystal, weak C—H···O hydrogen bonds connect molecules into a two-dimensional network (Fig. 2) parallel to (001).