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

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.

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

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Computing details

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

Crystal data

C18H13FN4O4S	F(000) = 1648
Mr = 400.38	Dx = 1.503 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2271 reflections
a = 21.269 (5) Å	θ = 2.6–26.2°
b = 10.594 (3) Å	µ = 0.23 mm^−1
c = 15.758 (4) Å	T = 294 K
β = 94.823 (4)°	Block, white
V = 3538.0 (15) Å^3	0.22 × 0.14 × 0.06 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	3609 independent reflections
Radiation source: fine-focus sealed tube	2137 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
φ and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→26
Tmin = 0.952, Tmax = 0.987	k = −10→13
9516 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0309P)^2 + 4.2871P] where P = (Fo^2 + 2Fc^2)/3
3609 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.46 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.09799 (4)	1.10311 (8)	0.18015 (5)	0.0345 (2)
F1	0.24459 (9)	1.1861 (2)	0.10770 (12)	0.0567 (6)
O1	0.20847 (10)	0.8274 (2)	0.21705 (14)	0.0417 (6)
O2	0.07827 (10)	1.1636 (2)	0.25411 (14)	0.0467 (6)
O3	0.10225 (10)	1.1785 (2)	0.10592 (14)	0.0495 (6)
O4	0.31159 (10)	0.9989 (2)	0.32345 (14)	0.0480 (6)
N1	0.16772 (10)	1.0281 (2)	0.20604 (15)	0.0294 (6)
N2	0.19839 (11)	1.0819 (2)	0.35164 (15)	0.0332 (6)
N3	0.16996 (13)	0.9767 (3)	0.38016 (17)	0.0471 (8)
N4	0.19232 (14)	1.1166 (3)	0.48747 (17)	0.0545 (8)
C1	0.05829 (14)	0.9609 (3)	0.15640 (19)	0.0366 (8)
C2	−0.00516 (15)	0.9465 (4)	0.1305 (2)	0.0511 (10)
H2	−0.0318	1.0157	0.1218	0.061*
C3	−0.02702 (17)	0.8241 (4)	0.1183 (3)	0.0651 (12)
H3	−0.0695	0.8103	0.1020	0.078*
C4	0.01331 (17)	0.7223 (4)	0.1299 (3)	0.0638 (12)
H4	−0.0027	0.6412	0.1210	0.077*
C5	0.07684 (16)	0.7375 (3)	0.1544 (2)	0.0507 (10)
H5	0.1037	0.6683	0.1616	0.061*
C6	0.09904 (14)	0.8593 (3)	0.16799 (19)	0.0352 (8)
C7	0.16423 (14)	0.8960 (3)	0.19963 (18)	0.0316 (7)
C8	0.21540 (13)	1.0891 (3)	0.26417 (18)	0.0316 (7)
H8	0.2166	1.1786	0.2486	0.038*
C9	0.21152 (16)	1.1614 (3)	0.4165 (2)	0.0450 (9)
H9	0.2317	1.2386	0.4118	0.054*
C10	0.16791 (16)	1.0042 (4)	0.4617 (2)	0.0532 (10)
H10	0.1506	0.9489	0.4993	0.064*
C11	0.28262 (14)	1.0343 (3)	0.2582 (2)	0.0356 (8)
C12	0.31250 (13)	1.0327 (3)	0.17558 (19)	0.0329 (7)
C13	0.29419 (14)	1.1059 (3)	0.1049 (2)	0.0396 (8)
C14	0.32471 (16)	1.1012 (4)	0.0316 (2)	0.0492 (9)
H14	0.3113	1.1513	−0.0149	0.059*
C15	0.37540 (16)	1.0214 (4)	0.0279 (2)	0.0522 (10)
H15	0.3959	1.0173	−0.0219	0.063*
C16	0.39676 (16)	0.9468 (3)	0.0969 (2)	0.0455 (9)
C17	0.36486 (14)	0.9543 (3)	0.1696 (2)	0.0396 (8)
H17	0.3788	0.9053	0.2165	0.048*
C18	0.45266 (19)	0.8593 (4)	0.0922 (3)	0.0743 (13)
H18A	0.4740	0.8497	0.1479	0.111*
H18B	0.4812	0.8944	0.0544	0.111*
H18C	0.4382	0.7784	0.0712	0.111*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0332 (4)	0.0359 (4)	0.0346 (5)	0.0051 (4)	0.0041 (3)	−0.0050 (4)
F1	0.0508 (12)	0.0746 (15)	0.0457 (13)	0.0182 (11)	0.0093 (9)	0.0220 (11)
O1	0.0359 (12)	0.0378 (13)	0.0504 (15)	0.0085 (11)	−0.0021 (11)	−0.0008 (11)
O2	0.0458 (13)	0.0466 (14)	0.0485 (15)	0.0063 (12)	0.0091 (11)	−0.0168 (11)
O3	0.0512 (14)	0.0519 (16)	0.0455 (15)	0.0145 (12)	0.0045 (11)	0.0132 (12)
O4	0.0413 (13)	0.0702 (18)	0.0319 (14)	0.0048 (12)	0.0004 (10)	0.0090 (12)
N1	0.0283 (13)	0.0325 (14)	0.0272 (14)	0.0014 (12)	0.0004 (10)	−0.0038 (11)
N2	0.0337 (14)	0.0420 (16)	0.0244 (14)	−0.0067 (13)	0.0049 (11)	−0.0034 (12)
N3	0.0547 (18)	0.0521 (19)	0.0359 (18)	−0.0169 (15)	0.0129 (14)	0.0021 (14)
N4	0.066 (2)	0.069 (2)	0.0296 (17)	−0.0098 (18)	0.0101 (14)	−0.0071 (16)
C1	0.0334 (17)	0.042 (2)	0.0349 (19)	−0.0008 (16)	0.0039 (14)	−0.0123 (15)
C2	0.0328 (19)	0.054 (2)	0.065 (3)	0.0081 (18)	−0.0043 (17)	−0.0140 (19)
C3	0.036 (2)	0.070 (3)	0.088 (3)	−0.004 (2)	−0.005 (2)	−0.028 (2)
C4	0.046 (2)	0.052 (3)	0.092 (3)	−0.013 (2)	−0.002 (2)	−0.024 (2)
C5	0.043 (2)	0.040 (2)	0.068 (3)	0.0006 (18)	−0.0042 (18)	−0.0133 (18)
C6	0.0318 (17)	0.0384 (18)	0.0354 (19)	−0.0007 (16)	0.0022 (14)	−0.0094 (15)
C7	0.0376 (17)	0.0331 (18)	0.0244 (17)	0.0018 (16)	0.0048 (13)	−0.0045 (14)
C8	0.0344 (16)	0.0349 (18)	0.0257 (17)	−0.0073 (15)	0.0025 (13)	−0.0021 (14)
C9	0.051 (2)	0.047 (2)	0.036 (2)	−0.0066 (18)	0.0034 (17)	−0.0129 (17)
C10	0.056 (2)	0.068 (3)	0.037 (2)	−0.009 (2)	0.0140 (17)	0.0068 (19)
C11	0.0362 (18)	0.0410 (19)	0.0295 (19)	−0.0058 (16)	0.0017 (14)	0.0041 (15)
C12	0.0304 (16)	0.0374 (18)	0.0307 (18)	−0.0049 (15)	0.0021 (13)	0.0020 (15)
C13	0.0345 (17)	0.047 (2)	0.037 (2)	0.0002 (18)	0.0030 (14)	0.0064 (17)
C14	0.049 (2)	0.062 (2)	0.037 (2)	−0.001 (2)	0.0038 (16)	0.0118 (18)
C15	0.054 (2)	0.069 (3)	0.036 (2)	−0.004 (2)	0.0195 (17)	0.0009 (19)
C16	0.045 (2)	0.046 (2)	0.047 (2)	−0.0011 (17)	0.0153 (17)	0.0027 (17)
C17	0.0425 (19)	0.0382 (19)	0.039 (2)	−0.0027 (16)	0.0080 (15)	0.0054 (15)
C18	0.076 (3)	0.072 (3)	0.081 (3)	0.023 (2)	0.044 (2)	0.017 (2)

Geometric parameters (Å, º)

S1—O2	1.424 (2)	C4—H4	0.9300
S1—O3	1.425 (2)	C5—C6	1.384 (4)
S1—N1	1.701 (2)	C5—H5	0.9300
S1—C1	1.752 (3)	C6—C7	1.485 (4)
F1—C13	1.358 (4)	C8—C11	1.554 (4)
O1—C7	1.202 (3)	C8—H8	0.9800
O4—C11	1.213 (3)	C9—H9	0.9300
N1—C7	1.405 (4)	C10—H10	0.9300
N1—C8	1.459 (4)	C11—C12	1.496 (4)
N2—C9	1.335 (4)	C12—C13	1.386 (4)
N2—N3	1.362 (3)	C12—C17	1.399 (4)
N2—C8	1.456 (3)	C13—C14	1.373 (4)
N3—C10	1.322 (4)	C14—C15	1.375 (5)
N4—C9	1.312 (4)	C14—H14	0.9300
N4—C10	1.348 (4)	C15—C16	1.389 (5)
C1—C6	1.385 (4)	C15—H15	0.9300
C1—C2	1.385 (4)	C16—C17	1.383 (4)
C2—C3	1.386 (5)	C16—C18	1.514 (5)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.380 (5)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—C5	1.383 (5)	C18—H18C	0.9600
O2—S1—O3	117.59 (15)	N1—C8—C11	113.0 (2)
O2—S1—N1	108.94 (13)	N2—C8—H8	107.6
O3—S1—N1	110.13 (13)	N1—C8—H8	107.6
O2—S1—C1	113.07 (14)	C11—C8—H8	107.6
O3—S1—C1	111.66 (15)	N4—C9—N2	111.4 (3)
N1—S1—C1	92.55 (14)	N4—C9—H9	124.3
C7—N1—C8	121.1 (2)	N2—C9—H9	124.3
C7—N1—S1	114.1 (2)	N3—C10—N4	116.3 (3)
C8—N1—S1	119.29 (19)	N3—C10—H10	121.8
C9—N2—N3	109.5 (3)	N4—C10—H10	121.8
C9—N2—C8	129.7 (3)	O4—C11—C12	120.8 (3)
N3—N2—C8	120.5 (2)	O4—C11—C8	117.9 (3)
C10—N3—N2	101.1 (3)	C12—C11—C8	121.2 (3)
C9—N4—C10	101.7 (3)	C13—C12—C17	116.8 (3)
C6—C1—C2	122.5 (3)	C13—C12—C11	125.6 (3)
C6—C1—S1	110.8 (2)	C17—C12—C11	117.6 (3)
C2—C1—S1	126.7 (3)	F1—C13—C14	118.3 (3)
C1—C2—C3	116.8 (3)	F1—C13—C12	119.4 (3)
C1—C2—H2	121.6	C14—C13—C12	122.4 (3)
C3—C2—H2	121.6	C13—C14—C15	119.0 (3)
C4—C3—C2	121.0 (3)	C13—C14—H14	120.5
C4—C3—H3	119.5	C15—C14—H14	120.5
C2—C3—H3	119.5	C14—C15—C16	121.6 (3)
C3—C4—C5	121.8 (4)	C14—C15—H15	119.2
C3—C4—H4	119.1	C16—C15—H15	119.2
C5—C4—H4	119.1	C17—C16—C15	117.7 (3)
C4—C5—C6	117.6 (3)	C17—C16—C18	121.2 (3)
C4—C5—H5	121.2	C15—C16—C18	121.1 (3)
C6—C5—H5	121.2	C16—C17—C12	122.6 (3)
C5—C6—C1	120.2 (3)	C16—C17—H17	118.7
C5—C6—C7	126.3 (3)	C12—C17—H17	118.7
C1—C6—C7	113.4 (3)	C16—C18—H18A	109.5
O1—C7—N1	123.4 (3)	C16—C18—H18B	109.5
O1—C7—C6	127.5 (3)	H18A—C18—H18B	109.5
N1—C7—C6	109.1 (3)	C16—C18—H18C	109.5
N2—C8—N1	110.9 (2)	H18A—C18—H18C	109.5
N2—C8—C11	109.9 (2)	H18B—C18—H18C	109.5
O2—S1—N1—C7	114.4 (2)	N3—N2—C8—N1	37.3 (4)
O3—S1—N1—C7	−115.2 (2)	C9—N2—C8—C11	84.5 (4)
C1—S1—N1—C7	−1.0 (2)	N3—N2—C8—C11	−88.4 (3)
O2—S1—N1—C8	−39.7 (2)	C7—N1—C8—N2	−76.7 (3)
O3—S1—N1—C8	90.7 (2)	S1—N1—C8—N2	75.5 (3)
C1—S1—N1—C8	−155.1 (2)	C7—N1—C8—C11	47.2 (3)
C9—N2—N3—C10	0.7 (3)	S1—N1—C8—C11	−160.5 (2)
C8—N2—N3—C10	174.9 (3)	C10—N4—C9—N2	1.1 (4)
O2—S1—C1—C6	−112.3 (2)	N3—N2—C9—N4	−1.2 (4)
O3—S1—C1—C6	112.4 (2)	C8—N2—C9—N4	−174.7 (3)
N1—S1—C1—C6	−0.5 (2)	N2—N3—C10—N4	0.0 (4)
O2—S1—C1—C2	66.8 (3)	C9—N4—C10—N3	−0.7 (4)
O3—S1—C1—C2	−68.5 (3)	N2—C8—C11—O4	−2.6 (4)
N1—S1—C1—C2	178.7 (3)	N1—C8—C11—O4	−127.0 (3)
C6—C1—C2—C3	1.4 (5)	N2—C8—C11—C12	−178.6 (3)
S1—C1—C2—C3	−177.6 (3)	N1—C8—C11—C12	56.9 (4)
C1—C2—C3—C4	−1.3 (6)	O4—C11—C12—C13	−157.3 (3)
C2—C3—C4—C5	0.3 (6)	C8—C11—C12—C13	18.6 (5)
C3—C4—C5—C6	0.6 (6)	O4—C11—C12—C17	20.2 (4)
C4—C5—C6—C1	−0.5 (5)	C8—C11—C12—C17	−163.9 (3)
C4—C5—C6—C7	175.9 (3)	C17—C12—C13—F1	−178.4 (3)
C2—C1—C6—C5	−0.6 (5)	C11—C12—C13—F1	−0.9 (5)
S1—C1—C6—C5	178.6 (3)	C17—C12—C13—C14	1.2 (5)
C2—C1—C6—C7	−177.4 (3)	C11—C12—C13—C14	178.7 (3)
S1—C1—C6—C7	1.8 (3)	F1—C13—C14—C15	179.4 (3)
C8—N1—C7—O1	−24.9 (4)	C12—C13—C14—C15	−0.2 (5)
S1—N1—C7—O1	−178.4 (2)	C13—C14—C15—C16	−0.7 (6)
C8—N1—C7—C6	155.7 (2)	C14—C15—C16—C17	0.6 (5)
S1—N1—C7—C6	2.1 (3)	C14—C15—C16—C18	−180.0 (4)
C5—C6—C7—O1	1.5 (5)	C15—C16—C17—C12	0.4 (5)
C1—C6—C7—O1	178.1 (3)	C18—C16—C17—C12	−179.0 (3)
C5—C6—C7—N1	−179.1 (3)	C13—C12—C17—C16	−1.3 (5)
C1—C6—C7—N1	−2.5 (3)	C11—C12—C17—C16	−179.0 (3)
C9—N2—C8—N1	−149.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4^i	0.93	2.54	3.464 (4)	173
C8—H8···O1^ii	0.98	2.27	3.000 (4)	130
C10—H10···O3^iii	0.93	2.45	3.375 (4)	175
C14—H14···F1^iv	0.93	2.49	3.394 (4)	163

Symmetry codes: (i) −x+1/2, y−1/2, −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.