N-[4-(2,4-Difluoro­phen­yl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thia­zol-2-yl]-2-fluoro­benzamide

As part of a search for potent fungicidal agents, the title compound, C₁₈H₁₀F₃N₅OS, has been synthesized and its structure determined. In the crystal structure, the mol­ecules are linked by inter­molecular N—H...N hydrogen bonds. The dihedral angles between the planes of the thia­zole and triazole rings, and between the thia­zole and 2,4-difluoro­phenyl rings are 58.6 (2) and 45.3 (3)°, respectively.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.033
• wR factor = 0.077
• Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT431_ALERT_2_A Short Inter HL..A Contact  F1     ..  F3'     ..       2.42 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.88 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C13    -   C14    ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C14    -   C15    ...       1.37 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C3     ..  F3'     ..       2.90 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       9.20 Deg.
              C14  -F3   -H14A    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       3.60 Deg.
              F3   -C14  -H14A    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       7.40 Deg.
              F3'  -C18  -H18A    1.555   1.555   1.555
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.08

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           26.34
           From the CIF: _reflns_number_total               2348
           Count of symmetry unique reflns         1816
           Completeness (_total/calc)            129.30%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       532
           Fraction of Friedel pairs measured     0.293
           Are heavy atom types Z>Si present        yes

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  14 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); 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.

N-[4-(2,4-Difluorophenyl]-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazol-2-yl]-2- fluorobenzamide

Crystal data

C18H10F3N5OS	F(000) = 816
Mr = 401.37	Dx = 1.501 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 6.986 (2) Å	Cell parameters from 1764 reflections
b = 24.629 (7) Å	θ = 3.0–23.7°
c = 10.333 (3) Å	µ = 0.23 mm^−1
β = 92.399 (5)°	T = 294 K
V = 1776.3 (9) Å^3	Plate, colorless
Z = 4	0.26 × 0.22 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2348 independent reflections
Radiation source: fine-focus sealed tube	1770 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 26.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.942, Tmax = 0.964	k = −30→27
4739 measured reflections	l = −6→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0402P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2348 reflections	Δρmax = 0.14 e Å^−3
267 parameters	Δρmin = −0.21 e Å^−3
4 restraints	Absolute structure: Flack (1983), 547 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)

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	Occ. (<1)
S1	0.67979 (11)	0.91503 (3)	0.02177 (9)	0.0446 (2)
F1	0.8945 (3)	1.22209 (8)	0.2711 (3)	0.0907 (9)
F2	0.4278 (3)	1.09395 (8)	0.1507 (3)	0.0813 (8)
O1	0.4150 (4)	0.83399 (10)	0.0388 (3)	0.0626 (8)
N1	0.3856 (4)	0.90125 (11)	0.1855 (3)	0.0402 (7)
H1	0.312 (4)	0.9208 (12)	0.243 (3)	0.048 (10)*
N2	0.5473 (4)	0.98416 (10)	0.1853 (3)	0.0378 (6)
N3	0.9416 (3)	0.99340 (10)	−0.0357 (3)	0.0375 (7)
N4	1.1112 (4)	0.96503 (12)	−0.0230 (3)	0.0522 (8)
N5	1.1382 (4)	1.03805 (11)	−0.1540 (3)	0.0462 (7)
C1	0.9405 (5)	1.08122 (13)	0.1868 (4)	0.0478 (9)
H1A	1.0367	1.0555	0.1785	0.057*
C2	0.9891 (5)	1.13361 (15)	0.2230 (4)	0.0559 (10)
H2	1.1166	1.1432	0.2395	0.067*
C3	0.8470 (6)	1.17090 (13)	0.2341 (4)	0.0570 (10)
C4	0.6583 (6)	1.15855 (14)	0.2122 (4)	0.0601 (11)
H4	0.5632	1.1845	0.2216	0.072*
C5	0.6140 (5)	1.10656 (14)	0.1759 (4)	0.0469 (9)
C6	0.7495 (4)	1.06606 (12)	0.1622 (3)	0.0373 (8)
C7	0.6964 (4)	1.01004 (12)	0.1257 (3)	0.0356 (8)
C8	0.5251 (4)	0.93498 (12)	0.1399 (3)	0.0365 (8)
C9	0.7837 (4)	0.97867 (12)	0.0383 (3)	0.0365 (8)
C10	0.9626 (5)	1.03592 (13)	−0.1127 (4)	0.0450 (9)
H10	0.8665	1.0608	−0.1345	0.054*
C11	1.2198 (5)	0.99421 (16)	−0.0967 (4)	0.0526 (10)
H11	1.3470	0.9851	−0.1088	0.063*
C12	0.3331 (5)	0.85369 (12)	0.1299 (4)	0.0436 (9)
F3	0.2740 (5)	0.83953 (12)	0.4006 (3)	0.0901 (13)	0.896 (8)
F3'	0.055 (4)	0.8032 (12)	−0.0252 (13)	0.111 (13)	0.104 (8)
C13	0.1614 (5)	0.82774 (13)	0.1862 (4)	0.0467 (9)
C14	0.1359 (6)	0.82332 (15)	0.3166 (4)	0.0607 (11)
H14A	0.2342	0.8373	0.3751	0.073*	0.104 (8)
C15	−0.0241 (8)	0.80027 (18)	0.3661 (6)	0.0928 (18)
H15A	−0.0363	0.7971	0.4551	0.111*
C16	−0.1653 (8)	0.7820 (2)	0.2811 (9)	0.103 (2)
H16A	−0.2766	0.7675	0.3133	0.124*
C17	−0.1467 (6)	0.78448 (17)	0.1505 (8)	0.0905 (18)
H17A	−0.2434	0.7713	0.0945	0.109*
C18	0.0187 (6)	0.80700 (15)	0.1013 (6)	0.0675 (12)
H18A	0.0337	0.8082	0.0124	0.081*	0.896 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0406 (5)	0.0422 (4)	0.0526 (5)	0.0006 (4)	0.0212 (4)	−0.0045 (4)
F1	0.0797 (17)	0.0422 (12)	0.150 (3)	−0.0062 (11)	−0.0029 (18)	−0.0159 (13)
F2	0.0340 (12)	0.0669 (15)	0.143 (3)	0.0102 (10)	0.0019 (14)	−0.0125 (14)
O1	0.0613 (17)	0.0576 (14)	0.0707 (19)	−0.0064 (13)	0.0239 (15)	−0.0173 (14)
N1	0.0332 (15)	0.0388 (15)	0.0498 (19)	−0.0029 (12)	0.0170 (14)	−0.0023 (13)
N2	0.0313 (14)	0.0386 (15)	0.0445 (16)	−0.0005 (11)	0.0121 (13)	0.0006 (13)
N3	0.0284 (14)	0.0406 (15)	0.0446 (17)	0.0057 (11)	0.0155 (13)	0.0042 (13)
N4	0.0391 (17)	0.0627 (19)	0.056 (2)	0.0126 (14)	0.0164 (15)	0.0153 (15)
N5	0.0367 (15)	0.0541 (18)	0.0490 (17)	−0.0021 (14)	0.0162 (14)	0.0059 (15)
C1	0.0368 (19)	0.044 (2)	0.063 (3)	0.0051 (16)	0.0093 (18)	0.0001 (19)
C2	0.039 (2)	0.053 (2)	0.075 (3)	−0.0067 (17)	0.003 (2)	−0.002 (2)
C3	0.057 (2)	0.0353 (19)	0.079 (3)	−0.0033 (16)	0.008 (2)	0.0026 (18)
C4	0.049 (2)	0.042 (2)	0.090 (3)	0.0134 (17)	0.014 (2)	−0.002 (2)
C5	0.0311 (19)	0.049 (2)	0.060 (2)	0.0032 (15)	0.0059 (18)	0.0019 (18)
C6	0.0306 (17)	0.0385 (17)	0.044 (2)	0.0019 (14)	0.0125 (15)	0.0009 (15)
C7	0.0273 (17)	0.0414 (18)	0.039 (2)	0.0029 (13)	0.0082 (15)	0.0057 (15)
C8	0.0294 (16)	0.0386 (18)	0.042 (2)	0.0066 (14)	0.0072 (16)	0.0012 (14)
C9	0.0328 (18)	0.0362 (18)	0.041 (2)	0.0021 (13)	0.0112 (16)	0.0026 (14)
C10	0.041 (2)	0.0483 (19)	0.047 (2)	0.0050 (16)	0.0136 (17)	0.0027 (17)
C11	0.0314 (19)	0.078 (3)	0.049 (2)	0.0037 (19)	0.0154 (18)	0.010 (2)
C12	0.0375 (19)	0.0370 (18)	0.057 (2)	0.0032 (15)	0.0077 (18)	−0.0016 (17)
F3	0.117 (3)	0.096 (2)	0.0570 (19)	−0.0387 (18)	0.0032 (18)	0.0041 (15)
F3'	0.13 (3)	0.11 (2)	0.09 (2)	−0.057 (19)	−0.025 (19)	−0.006 (17)
C13	0.0362 (19)	0.0369 (18)	0.068 (3)	−0.0035 (15)	0.0097 (19)	−0.0004 (18)
C14	0.062 (3)	0.054 (2)	0.068 (3)	−0.009 (2)	0.021 (2)	−0.003 (2)
C15	0.104 (4)	0.072 (3)	0.107 (4)	−0.024 (3)	0.055 (4)	0.000 (3)
C16	0.067 (3)	0.071 (3)	0.176 (7)	−0.015 (3)	0.049 (4)	0.011 (4)
C17	0.046 (3)	0.055 (3)	0.168 (6)	−0.009 (2)	−0.015 (3)	0.014 (3)
C18	0.053 (2)	0.051 (2)	0.097 (4)	−0.006 (2)	−0.009 (3)	0.003 (2)

Geometric parameters (Å, º)

S1—C9	1.733 (3)	C4—C5	1.366 (5)
S1—C8	1.734 (3)	C4—H4	0.9300
F1—C3	1.355 (4)	C5—C6	1.386 (4)
F2—C5	1.352 (4)	C6—C7	1.474 (4)
O1—C12	1.222 (4)	C7—C9	1.353 (4)
N1—C12	1.349 (4)	C10—H10	0.9300
N1—C8	1.379 (4)	C11—H11	0.9300
N1—H1	0.94 (3)	C12—C13	1.498 (4)
N2—C8	1.306 (4)	F3—C14	1.332 (5)
N2—C7	1.387 (4)	F3—H14A	0.3788
N3—C10	1.327 (4)	F3'—C18	1.346 (10)
N3—N4	1.377 (4)	C13—C14	1.371 (6)
N3—C9	1.415 (4)	C13—C18	1.396 (6)
N4—C11	1.312 (4)	C14—C15	1.371 (6)
N5—C10	1.317 (4)	C14—H14A	0.9599
N5—C11	1.347 (5)	C15—C16	1.369 (9)
C1—C2	1.382 (5)	C15—H15A	0.9300
C1—C6	1.398 (5)	C16—C17	1.363 (8)
C1—H1A	0.9300	C16—H16A	0.9300
C2—C3	1.361 (5)	C17—C18	1.396 (6)
C2—H2	0.9300	C17—H17A	0.9300
C3—C4	1.362 (5)	C18—H18A	0.9300
C9—S1—C8	86.86 (14)	N3—C9—S1	120.8 (2)
C12—N1—C8	124.1 (3)	N5—C10—N3	110.7 (3)
C12—N1—H1	124.7 (19)	N5—C10—H10	124.6
C8—N1—H1	108.9 (19)	N3—C10—H10	124.6
C8—N2—C7	110.3 (2)	N4—C11—N5	116.8 (3)
C10—N3—N4	109.9 (2)	N4—C11—H11	121.6
C10—N3—C9	129.4 (3)	N5—C11—H11	121.6
N4—N3—C9	120.4 (2)	O1—C12—N1	123.1 (3)
C11—N4—N3	100.6 (3)	O1—C12—C13	122.5 (3)
C10—N5—C11	102.0 (3)	N1—C12—C13	114.4 (3)
C2—C1—C6	121.4 (3)	C14—F3—H14A	9.2
C2—C1—H1A	119.3	C14—C13—C18	118.0 (4)
C6—C1—H1A	119.3	C14—C13—C12	123.7 (4)
C3—C2—C1	118.7 (3)	C18—C13—C12	118.3 (4)
C3—C2—H2	120.6	F3—C14—C13	119.8 (3)
C1—C2—H2	120.6	F3—C14—C15	117.4 (5)
F1—C3—C2	118.7 (3)	C13—C14—C15	122.8 (5)
F1—C3—C4	118.6 (3)	F3—C14—H14A	3.6
C2—C3—C4	122.7 (3)	C13—C14—H14A	118.1
C3—C4—C5	117.5 (3)	C15—C14—H14A	119.1
C3—C4—H4	121.3	C16—C15—C14	118.2 (6)
C5—C4—H4	121.3	C16—C15—H15A	120.9
F2—C5—C4	118.2 (3)	C14—C15—H15A	120.9
F2—C5—C6	118.1 (3)	C17—C16—C15	121.6 (5)
C4—C5—C6	123.7 (3)	C17—C16—H16A	119.2
C5—C6—C1	116.1 (3)	C15—C16—H16A	119.2
C5—C6—C7	122.3 (3)	C16—C17—C18	119.5 (6)
C1—C6—C7	121.6 (3)	C16—C17—H17A	120.2
C9—C7—N2	113.7 (3)	C18—C17—H17A	120.2
C9—C7—C6	126.2 (3)	F3'—C18—C17	121.4 (13)
N2—C7—C6	120.1 (2)	F3'—C18—C13	118.3 (13)
N2—C8—N1	120.7 (3)	C17—C18—C13	119.8 (5)
N2—C8—S1	116.6 (2)	F3'—C18—H18A	7.4
N1—C8—S1	122.7 (2)	C17—C18—H18A	120.1
C7—C9—N3	126.7 (3)	C13—C18—H18A	120.1
C7—C9—S1	112.6 (2)
C10—N3—N4—C11	−0.4 (4)	C10—N3—C9—C7	−53.9 (6)
C9—N3—N4—C11	−174.5 (3)	N4—N3—C9—C7	118.9 (4)
C6—C1—C2—C3	−0.3 (6)	C10—N3—C9—S1	125.6 (3)
C1—C2—C3—F1	179.2 (4)	N4—N3—C9—S1	−61.6 (4)
C1—C2—C3—C4	0.7 (6)	C8—S1—C9—C7	−1.4 (3)
F1—C3—C4—C5	−179.5 (4)	C8—S1—C9—N3	179.0 (3)
C2—C3—C4—C5	−1.0 (6)	C11—N5—C10—N3	0.0 (4)
C3—C4—C5—F2	−178.4 (4)	N4—N3—C10—N5	0.3 (4)
C3—C4—C5—C6	1.0 (6)	C9—N3—C10—N5	173.7 (3)
F2—C5—C6—C1	178.8 (3)	N3—N4—C11—N5	0.4 (4)
C4—C5—C6—C1	−0.6 (5)	C10—N5—C11—N4	−0.2 (5)
F2—C5—C6—C7	−2.0 (5)	C8—N1—C12—O1	5.7 (6)
C4—C5—C6—C7	178.6 (4)	C8—N1—C12—C13	−172.3 (3)
C2—C1—C6—C5	0.3 (5)	O1—C12—C13—C14	136.8 (4)
C2—C1—C6—C7	−178.9 (3)	N1—C12—C13—C14	−45.1 (5)
C8—N2—C7—C9	−1.0 (4)	O1—C12—C13—C18	−43.4 (5)
C8—N2—C7—C6	−179.5 (3)	N1—C12—C13—C18	134.6 (3)
C5—C6—C7—C9	136.2 (4)	C18—C13—C14—F3	175.8 (3)
C1—C6—C7—C9	−44.7 (5)	C12—C13—C14—F3	−4.4 (6)
C5—C6—C7—N2	−45.6 (5)	C18—C13—C14—C15	−1.0 (6)
C1—C6—C7—N2	133.5 (3)	C12—C13—C14—C15	178.8 (4)
C7—N2—C8—N1	179.6 (3)	F3—C14—C15—C16	−178.2 (4)
C7—N2—C8—S1	0.0 (4)	C13—C14—C15—C16	−1.3 (7)
C12—N1—C8—N2	168.8 (3)	C14—C15—C16—C17	2.4 (8)
C12—N1—C8—S1	−11.6 (5)	C15—C16—C17—C18	−1.1 (8)
C9—S1—C8—N2	0.8 (3)	C16—C17—C18—F3'	170.2 (18)
C9—S1—C8—N1	−178.8 (3)	C16—C17—C18—C13	−1.3 (6)
N2—C7—C9—N3	−178.7 (3)	C14—C13—C18—F3'	−169.5 (16)
C6—C7—C9—N3	−0.4 (5)	C12—C13—C18—F3'	10.7 (17)
N2—C7—C9—S1	1.7 (4)	C14—C13—C18—C17	2.3 (5)
C6—C7—C9—S1	180.0 (3)	C12—C13—C18—C17	−177.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N5^i	0.94 (3)	1.93 (3)	2.865 (4)	174 (3)

Symmetry code: (i) x−1, −y+2, z+1/2.