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In the title compound, C18H13FN4O4S, the dihedral angles between the planes of the triazole and the sulfobenzoimide ring and benzene ring are 87.69 (3) and 74.35 (2)°, respectively. There are weak inter­molecular hydrogen-bond inter­actions that assemble the mol­ecules into slabs parallel to the bc plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045752/sa2015sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045752/sa2015Isup2.hkl
Contains datablock I

CCDC reference: 630442

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.056
  • wR factor = 0.117
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C8 .. 3.00 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 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

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); 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, 1999); software used to prepare material for publication: SHELXTL.

2-Fluoro-5-methylphenyl (1H-1,2,4-triazol-1-yl)(1,1,3-trioxo-1,2-dihydro-1,2-benzothiazol-2-yl)methyl ketone top
Crystal data top
C18H13FN4O4SF(000) = 1648
Mr = 400.38Dx = 1.503 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2271 reflections
a = 21.269 (5) Åθ = 2.6–26.2°
b = 10.594 (3) ŵ = 0.23 mm1
c = 15.758 (4) ÅT = 294 K
β = 94.823 (4)°Block, white
V = 3538.0 (15) Å30.22 × 0.14 × 0.06 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
3609 independent reflections
Radiation source: fine-focus sealed tube2137 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2426
Tmin = 0.952, Tmax = 0.987k = 1013
9516 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0309P)2 + 4.2871P]
where P = (Fo2 + 2Fc2)/3
3609 reflections(Δ/σ)max < 0.001
254 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.46 e Å3
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
xyzUiso*/Ueq
S10.09799 (4)1.10311 (8)0.18015 (5)0.0345 (2)
F10.24459 (9)1.1861 (2)0.10770 (12)0.0567 (6)
O10.20847 (10)0.8274 (2)0.21705 (14)0.0417 (6)
O20.07827 (10)1.1636 (2)0.25411 (14)0.0467 (6)
O30.10225 (10)1.1785 (2)0.10592 (14)0.0495 (6)
O40.31159 (10)0.9989 (2)0.32345 (14)0.0480 (6)
N10.16772 (10)1.0281 (2)0.20604 (15)0.0294 (6)
N20.19839 (11)1.0819 (2)0.35164 (15)0.0332 (6)
N30.16996 (13)0.9767 (3)0.38016 (17)0.0471 (8)
N40.19232 (14)1.1166 (3)0.48747 (17)0.0545 (8)
C10.05829 (14)0.9609 (3)0.15640 (19)0.0366 (8)
C20.00516 (15)0.9465 (4)0.1305 (2)0.0511 (10)
H20.03181.01570.12180.061*
C30.02702 (17)0.8241 (4)0.1183 (3)0.0651 (12)
H30.06950.81030.10200.078*
C40.01331 (17)0.7223 (4)0.1299 (3)0.0638 (12)
H40.00270.64120.12100.077*
C50.07684 (16)0.7375 (3)0.1544 (2)0.0507 (10)
H50.10370.66830.16160.061*
C60.09904 (14)0.8593 (3)0.16799 (19)0.0352 (8)
C70.16423 (14)0.8960 (3)0.19963 (18)0.0316 (7)
C80.21540 (13)1.0891 (3)0.26417 (18)0.0316 (7)
H80.21661.17860.24860.038*
C90.21152 (16)1.1614 (3)0.4165 (2)0.0450 (9)
H90.23171.23860.41180.054*
C100.16791 (16)1.0042 (4)0.4617 (2)0.0532 (10)
H100.15060.94890.49930.064*
C110.28262 (14)1.0343 (3)0.2582 (2)0.0356 (8)
C120.31250 (13)1.0327 (3)0.17558 (19)0.0329 (7)
C130.29419 (14)1.1059 (3)0.1049 (2)0.0396 (8)
C140.32471 (16)1.1012 (4)0.0316 (2)0.0492 (9)
H140.31131.15130.01490.059*
C150.37540 (16)1.0214 (4)0.0279 (2)0.0522 (10)
H150.39591.01730.02190.063*
C160.39676 (16)0.9468 (3)0.0969 (2)0.0455 (9)
C170.36486 (14)0.9543 (3)0.1696 (2)0.0396 (8)
H170.37880.90530.21650.048*
C180.45266 (19)0.8593 (4)0.0922 (3)0.0743 (13)
H18A0.47400.84970.14790.111*
H18B0.48120.89440.05440.111*
H18C0.43820.77840.07120.111*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0332 (4)0.0359 (4)0.0346 (5)0.0051 (4)0.0041 (3)0.0050 (4)
F10.0508 (12)0.0746 (15)0.0457 (13)0.0182 (11)0.0093 (9)0.0220 (11)
O10.0359 (12)0.0378 (13)0.0504 (15)0.0085 (11)0.0021 (11)0.0008 (11)
O20.0458 (13)0.0466 (14)0.0485 (15)0.0063 (12)0.0091 (11)0.0168 (11)
O30.0512 (14)0.0519 (16)0.0455 (15)0.0145 (12)0.0045 (11)0.0132 (12)
O40.0413 (13)0.0702 (18)0.0319 (14)0.0048 (12)0.0004 (10)0.0090 (12)
N10.0283 (13)0.0325 (14)0.0272 (14)0.0014 (12)0.0004 (10)0.0038 (11)
N20.0337 (14)0.0420 (16)0.0244 (14)0.0067 (13)0.0049 (11)0.0034 (12)
N30.0547 (18)0.0521 (19)0.0359 (18)0.0169 (15)0.0129 (14)0.0021 (14)
N40.066 (2)0.069 (2)0.0296 (17)0.0098 (18)0.0101 (14)0.0071 (16)
C10.0334 (17)0.042 (2)0.0349 (19)0.0008 (16)0.0039 (14)0.0123 (15)
C20.0328 (19)0.054 (2)0.065 (3)0.0081 (18)0.0043 (17)0.0140 (19)
C30.036 (2)0.070 (3)0.088 (3)0.004 (2)0.005 (2)0.028 (2)
C40.046 (2)0.052 (3)0.092 (3)0.013 (2)0.002 (2)0.024 (2)
C50.043 (2)0.040 (2)0.068 (3)0.0006 (18)0.0042 (18)0.0133 (18)
C60.0318 (17)0.0384 (18)0.0354 (19)0.0007 (16)0.0022 (14)0.0094 (15)
C70.0376 (17)0.0331 (18)0.0244 (17)0.0018 (16)0.0048 (13)0.0045 (14)
C80.0344 (16)0.0349 (18)0.0257 (17)0.0073 (15)0.0025 (13)0.0021 (14)
C90.051 (2)0.047 (2)0.036 (2)0.0066 (18)0.0034 (17)0.0129 (17)
C100.056 (2)0.068 (3)0.037 (2)0.009 (2)0.0140 (17)0.0068 (19)
C110.0362 (18)0.0410 (19)0.0295 (19)0.0058 (16)0.0017 (14)0.0041 (15)
C120.0304 (16)0.0374 (18)0.0307 (18)0.0049 (15)0.0021 (13)0.0020 (15)
C130.0345 (17)0.047 (2)0.037 (2)0.0002 (18)0.0030 (14)0.0064 (17)
C140.049 (2)0.062 (2)0.037 (2)0.001 (2)0.0038 (16)0.0118 (18)
C150.054 (2)0.069 (3)0.036 (2)0.004 (2)0.0195 (17)0.0009 (19)
C160.045 (2)0.046 (2)0.047 (2)0.0011 (17)0.0153 (17)0.0027 (17)
C170.0425 (19)0.0382 (19)0.039 (2)0.0027 (16)0.0080 (15)0.0054 (15)
C180.076 (3)0.072 (3)0.081 (3)0.023 (2)0.044 (2)0.017 (2)
Geometric parameters (Å, º) top
S1—O21.424 (2)C4—H40.9300
S1—O31.425 (2)C5—C61.384 (4)
S1—N11.701 (2)C5—H50.9300
S1—C11.752 (3)C6—C71.485 (4)
F1—C131.358 (4)C8—C111.554 (4)
O1—C71.202 (3)C8—H80.9800
O4—C111.213 (3)C9—H90.9300
N1—C71.405 (4)C10—H100.9300
N1—C81.459 (4)C11—C121.496 (4)
N2—C91.335 (4)C12—C131.386 (4)
N2—N31.362 (3)C12—C171.399 (4)
N2—C81.456 (3)C13—C141.373 (4)
N3—C101.322 (4)C14—C151.375 (5)
N4—C91.312 (4)C14—H140.9300
N4—C101.348 (4)C15—C161.389 (5)
C1—C61.385 (4)C15—H150.9300
C1—C21.385 (4)C16—C171.383 (4)
C2—C31.386 (5)C16—C181.514 (5)
C2—H20.9300C17—H170.9300
C3—C41.380 (5)C18—H18A0.9600
C3—H30.9300C18—H18B0.9600
C4—C51.383 (5)C18—H18C0.9600
O2—S1—O3117.59 (15)N1—C8—C11113.0 (2)
O2—S1—N1108.94 (13)N2—C8—H8107.6
O3—S1—N1110.13 (13)N1—C8—H8107.6
O2—S1—C1113.07 (14)C11—C8—H8107.6
O3—S1—C1111.66 (15)N4—C9—N2111.4 (3)
N1—S1—C192.55 (14)N4—C9—H9124.3
C7—N1—C8121.1 (2)N2—C9—H9124.3
C7—N1—S1114.1 (2)N3—C10—N4116.3 (3)
C8—N1—S1119.29 (19)N3—C10—H10121.8
C9—N2—N3109.5 (3)N4—C10—H10121.8
C9—N2—C8129.7 (3)O4—C11—C12120.8 (3)
N3—N2—C8120.5 (2)O4—C11—C8117.9 (3)
C10—N3—N2101.1 (3)C12—C11—C8121.2 (3)
C9—N4—C10101.7 (3)C13—C12—C17116.8 (3)
C6—C1—C2122.5 (3)C13—C12—C11125.6 (3)
C6—C1—S1110.8 (2)C17—C12—C11117.6 (3)
C2—C1—S1126.7 (3)F1—C13—C14118.3 (3)
C1—C2—C3116.8 (3)F1—C13—C12119.4 (3)
C1—C2—H2121.6C14—C13—C12122.4 (3)
C3—C2—H2121.6C13—C14—C15119.0 (3)
C4—C3—C2121.0 (3)C13—C14—H14120.5
C4—C3—H3119.5C15—C14—H14120.5
C2—C3—H3119.5C14—C15—C16121.6 (3)
C3—C4—C5121.8 (4)C14—C15—H15119.2
C3—C4—H4119.1C16—C15—H15119.2
C5—C4—H4119.1C17—C16—C15117.7 (3)
C4—C5—C6117.6 (3)C17—C16—C18121.2 (3)
C4—C5—H5121.2C15—C16—C18121.1 (3)
C6—C5—H5121.2C16—C17—C12122.6 (3)
C5—C6—C1120.2 (3)C16—C17—H17118.7
C5—C6—C7126.3 (3)C12—C17—H17118.7
C1—C6—C7113.4 (3)C16—C18—H18A109.5
O1—C7—N1123.4 (3)C16—C18—H18B109.5
O1—C7—C6127.5 (3)H18A—C18—H18B109.5
N1—C7—C6109.1 (3)C16—C18—H18C109.5
N2—C8—N1110.9 (2)H18A—C18—H18C109.5
N2—C8—C11109.9 (2)H18B—C18—H18C109.5
O2—S1—N1—C7114.4 (2)N3—N2—C8—N137.3 (4)
O3—S1—N1—C7115.2 (2)C9—N2—C8—C1184.5 (4)
C1—S1—N1—C71.0 (2)N3—N2—C8—C1188.4 (3)
O2—S1—N1—C839.7 (2)C7—N1—C8—N276.7 (3)
O3—S1—N1—C890.7 (2)S1—N1—C8—N275.5 (3)
C1—S1—N1—C8155.1 (2)C7—N1—C8—C1147.2 (3)
C9—N2—N3—C100.7 (3)S1—N1—C8—C11160.5 (2)
C8—N2—N3—C10174.9 (3)C10—N4—C9—N21.1 (4)
O2—S1—C1—C6112.3 (2)N3—N2—C9—N41.2 (4)
O3—S1—C1—C6112.4 (2)C8—N2—C9—N4174.7 (3)
N1—S1—C1—C60.5 (2)N2—N3—C10—N40.0 (4)
O2—S1—C1—C266.8 (3)C9—N4—C10—N30.7 (4)
O3—S1—C1—C268.5 (3)N2—C8—C11—O42.6 (4)
N1—S1—C1—C2178.7 (3)N1—C8—C11—O4127.0 (3)
C6—C1—C2—C31.4 (5)N2—C8—C11—C12178.6 (3)
S1—C1—C2—C3177.6 (3)N1—C8—C11—C1256.9 (4)
C1—C2—C3—C41.3 (6)O4—C11—C12—C13157.3 (3)
C2—C3—C4—C50.3 (6)C8—C11—C12—C1318.6 (5)
C3—C4—C5—C60.6 (6)O4—C11—C12—C1720.2 (4)
C4—C5—C6—C10.5 (5)C8—C11—C12—C17163.9 (3)
C4—C5—C6—C7175.9 (3)C17—C12—C13—F1178.4 (3)
C2—C1—C6—C50.6 (5)C11—C12—C13—F10.9 (5)
S1—C1—C6—C5178.6 (3)C17—C12—C13—C141.2 (5)
C2—C1—C6—C7177.4 (3)C11—C12—C13—C14178.7 (3)
S1—C1—C6—C71.8 (3)F1—C13—C14—C15179.4 (3)
C8—N1—C7—O124.9 (4)C12—C13—C14—C150.2 (5)
S1—N1—C7—O1178.4 (2)C13—C14—C15—C160.7 (6)
C8—N1—C7—C6155.7 (2)C14—C15—C16—C170.6 (5)
S1—N1—C7—C62.1 (3)C14—C15—C16—C18180.0 (4)
C5—C6—C7—O11.5 (5)C15—C16—C17—C120.4 (5)
C1—C6—C7—O1178.1 (3)C18—C16—C17—C12179.0 (3)
C5—C6—C7—N1179.1 (3)C13—C12—C17—C161.3 (5)
C1—C6—C7—N12.5 (3)C11—C12—C17—C16179.0 (3)
C9—N2—C8—N1149.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O4i0.932.543.464 (4)173
C8—H8···O1ii0.982.273.000 (4)130
C10—H10···O3iii0.932.453.375 (4)175
C14—H14···F1iv0.932.493.394 (4)163
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y+2, z+1/2; (iv) x+1/2, y+5/2, z.
 

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