(4-Fluoro­benzoyl)(1H-1,2,4-triazol-1-yl)­methyl morpholine-4-carbodi­thio­ate

In the title compound, C₁₅H₁₅FN₄O₂S₂, the morpholine ring adopts a chair conformation. The dihedral angle between the benzene and triazole rings is 77.1 (7)°. There are some weak intermolecular and intramolecular interactions in the crystal structure, providing stabilization.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.053
• wR factor = 0.112
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         C8
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

   0 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

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

(4-Fluorobenzoyl)(1H-1,2,4-triazol-1-yl)methyl morpholine-4-carbodithioate

Crystal data

C15H15FN4O2S2	Z = 2
Mr = 366.45	F(000) = 380
Triclinic, P1	Dx = 1.435 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.508 (2) Å	Cell parameters from 20 reflections
b = 7.605 (2) Å	θ = 2–11°
c = 16.271 (3) Å	µ = 0.34 mm^−1
α = 79.23 (3)°	T = 293 K
β = 81.42 (3)°	Block, yellow
γ = 68.91 (3)°	0.20 × 0.20 × 0.18 mm
V = 848.1 (4) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	2060 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 26.4°, θmin = 2.6°
ω scans	h = −9→9
4932 measured reflections	k = −9→8
3441 independent reflections	l = −11→20

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0442P)^2] where P = (Fo^2 + 2Fc^2)/3
3441 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.20 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
F1	0.8334 (4)	−0.3755 (3)	0.57762 (16)	0.1234 (10)
S1	0.80769 (10)	0.12726 (13)	0.14103 (5)	0.0528 (3)
S2	0.92595 (10)	0.34443 (12)	0.24833 (5)	0.0471 (2)
O1	0.6520 (4)	0.4788 (3)	0.41874 (13)	0.0703 (7)
O2	1.4104 (3)	0.2873 (3)	−0.01068 (13)	0.0643 (6)
N1	0.5457 (3)	0.5461 (4)	0.26046 (14)	0.0468 (6)
N2	0.3730 (4)	0.5543 (4)	0.24285 (18)	0.0679 (8)
N3	0.3812 (5)	0.8496 (5)	0.23571 (19)	0.0785 (9)
N4	1.1187 (3)	0.2256 (3)	0.11104 (13)	0.0404 (6)
C1	0.2832 (6)	0.7391 (6)	0.2286 (2)	0.0809 (12)
H1A	0.1575	0.7901	0.2142	0.097*
C2	0.5456 (6)	0.7224 (5)	0.2564 (2)	0.0671 (10)
H2A	0.6493	0.7518	0.2669	0.081*
C3	0.6842 (4)	0.3643 (4)	0.29037 (16)	0.0401 (7)
H3A	0.6516	0.2615	0.2751	0.048*
C4	0.6865 (4)	0.3381 (4)	0.38609 (17)	0.0435 (7)
C5	0.7304 (4)	0.1449 (4)	0.43455 (18)	0.0433 (7)
C6	0.7884 (5)	−0.0175 (5)	0.3964 (2)	0.0626 (9)
H6A	0.8022	−0.0076	0.3381	0.075*
C7	0.8257 (6)	−0.1937 (5)	0.4448 (3)	0.0821 (12)
H7A	0.8672	−0.3038	0.4199	0.099*
C8	0.8007 (6)	−0.2036 (6)	0.5297 (3)	0.0739 (11)
C9	0.7455 (5)	−0.0491 (6)	0.5695 (2)	0.0736 (11)
H9A	0.7308	−0.0612	0.6278	0.088*
C10	0.7116 (4)	0.1264 (5)	0.5212 (2)	0.0610 (9)
H10A	0.6755	0.2345	0.5473	0.073*
C11	0.9592 (4)	0.2262 (4)	0.15865 (16)	0.0356 (6)
C12	1.2628 (4)	0.2958 (4)	0.13155 (17)	0.0472 (8)
H12B	1.3687	0.1892	0.1546	0.057*
H12A	1.2064	0.3798	0.1737	0.057*
C13	1.3357 (4)	0.4013 (5)	0.05449 (19)	0.0556 (8)
H13B	1.2319	0.5149	0.0349	0.067*
H13A	1.4352	0.4410	0.0686	0.067*
C14	1.2647 (5)	0.2340 (5)	−0.03323 (19)	0.0626 (9)
H14B	1.3158	0.1594	−0.0790	0.075*
H14A	1.1616	0.3478	−0.0531	0.075*
C15	1.1861 (4)	0.1205 (5)	0.03833 (18)	0.0523 (8)
H15B	1.0806	0.0951	0.0211	0.063*
H15A	1.2849	−0.0006	0.0541	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.174 (3)	0.0761 (18)	0.112 (2)	−0.0467 (18)	−0.0487 (18)	0.0415 (15)
S1	0.0402 (4)	0.0713 (6)	0.0589 (5)	−0.0264 (4)	0.0037 (4)	−0.0299 (4)
S2	0.0444 (5)	0.0627 (6)	0.0433 (5)	−0.0266 (4)	0.0065 (3)	−0.0212 (4)
O1	0.1060 (19)	0.0528 (16)	0.0501 (14)	−0.0226 (14)	0.0065 (12)	−0.0222 (11)
O2	0.0562 (14)	0.0826 (18)	0.0593 (15)	−0.0348 (13)	0.0217 (11)	−0.0216 (12)
N1	0.0483 (16)	0.0428 (17)	0.0477 (15)	−0.0141 (13)	−0.0003 (12)	−0.0091 (11)
N2	0.0526 (18)	0.058 (2)	0.089 (2)	−0.0117 (16)	−0.0128 (15)	−0.0120 (16)
N3	0.094 (3)	0.051 (2)	0.076 (2)	−0.006 (2)	−0.0157 (18)	−0.0057 (16)
N4	0.0389 (13)	0.0475 (16)	0.0398 (14)	−0.0201 (12)	0.0033 (11)	−0.0131 (11)
C1	0.070 (3)	0.062 (3)	0.093 (3)	0.002 (2)	−0.020 (2)	−0.006 (2)
C2	0.084 (3)	0.049 (2)	0.072 (2)	−0.027 (2)	−0.012 (2)	−0.0044 (18)
C3	0.0397 (16)	0.0389 (19)	0.0427 (17)	−0.0150 (14)	0.0032 (13)	−0.0105 (13)
C4	0.0412 (17)	0.048 (2)	0.0425 (18)	−0.0170 (15)	0.0067 (13)	−0.0144 (15)
C5	0.0364 (16)	0.046 (2)	0.0470 (19)	−0.0144 (14)	−0.0003 (13)	−0.0078 (14)
C6	0.087 (3)	0.054 (2)	0.054 (2)	−0.031 (2)	−0.0116 (18)	−0.0056 (17)
C7	0.120 (3)	0.049 (3)	0.086 (3)	−0.032 (2)	−0.035 (2)	−0.003 (2)
C8	0.083 (3)	0.062 (3)	0.074 (3)	−0.029 (2)	−0.027 (2)	0.021 (2)
C9	0.072 (3)	0.077 (3)	0.052 (2)	−0.008 (2)	−0.0093 (18)	0.005 (2)
C10	0.057 (2)	0.060 (2)	0.051 (2)	−0.0026 (18)	−0.0001 (15)	−0.0090 (17)
C11	0.0309 (15)	0.0369 (17)	0.0377 (16)	−0.0096 (13)	−0.0004 (12)	−0.0081 (12)
C12	0.0397 (17)	0.058 (2)	0.0480 (18)	−0.0221 (16)	0.0012 (13)	−0.0101 (15)
C13	0.0522 (19)	0.059 (2)	0.059 (2)	−0.0272 (17)	0.0068 (15)	−0.0085 (16)
C14	0.055 (2)	0.085 (3)	0.049 (2)	−0.026 (2)	0.0125 (16)	−0.0228 (18)
C15	0.0460 (18)	0.061 (2)	0.0529 (19)	−0.0191 (16)	0.0120 (15)	−0.0280 (16)

Geometric parameters (Å, º)

F1—C8	1.350 (4)	C5—C10	1.382 (4)
S1—C11	1.654 (3)	C5—C6	1.386 (4)
S2—C11	1.794 (3)	C6—C7	1.377 (5)
S2—C3	1.805 (3)	C6—H6A	0.9300
O1—C4	1.211 (3)	C7—C8	1.356 (5)
O2—C14	1.411 (3)	C7—H7A	0.9300
O2—C13	1.417 (3)	C8—C9	1.351 (5)
N1—C2	1.330 (4)	C9—C10	1.373 (5)
N1—N2	1.347 (3)	C9—H9A	0.9300
N1—C3	1.447 (4)	C10—H10A	0.9300
N2—C1	1.314 (4)	C12—C13	1.500 (4)
N3—C2	1.310 (4)	C12—H12B	0.9700
N3—C1	1.329 (4)	C12—H12A	0.9700
N4—C11	1.325 (3)	C13—H13B	0.9700
N4—C12	1.469 (3)	C13—H13A	0.9700
N4—C15	1.476 (3)	C14—C15	1.495 (4)
C1—H1A	0.9300	C14—H14B	0.9700
C2—H2A	0.9300	C14—H14A	0.9700
C3—C4	1.535 (4)	C15—H15B	0.9700
C3—H3A	0.9800	C15—H15A	0.9700
C4—C5	1.478 (4)
C11—S2—C3	102.86 (12)	F1—C8—C7	119.1 (4)
C14—O2—C13	109.5 (2)	C9—C8—C7	123.3 (4)
C2—N1—N2	109.0 (3)	C8—C9—C10	118.0 (4)
C2—N1—C3	130.7 (3)	C8—C9—H9A	121.0
N2—N1—C3	119.6 (3)	C10—C9—H9A	121.0
C1—N2—N1	101.5 (3)	C9—C10—C5	121.0 (3)
C2—N3—C1	101.3 (3)	C9—C10—H10A	119.5
C11—N4—C12	125.1 (2)	C5—C10—H10A	119.5
C11—N4—C15	121.8 (2)	N4—C11—S1	125.4 (2)
C12—N4—C15	112.2 (2)	N4—C11—S2	111.93 (19)
N2—C1—N3	116.6 (4)	S1—C11—S2	122.67 (15)
N2—C1—H1A	121.7	N4—C12—C13	110.4 (2)
N3—C1—H1A	121.7	N4—C12—H12B	109.6
N3—C2—N1	111.5 (3)	C13—C12—H12B	109.6
N3—C2—H2A	124.2	N4—C12—H12A	109.6
N1—C2—H2A	124.2	C13—C12—H12A	109.6
N1—C3—C4	110.9 (2)	H12B—C12—H12A	108.1
N1—C3—S2	112.3 (2)	O2—C13—C12	111.7 (3)
C4—C3—S2	105.33 (18)	O2—C13—H13B	109.3
N1—C3—H3A	109.4	C12—C13—H13B	109.3
C4—C3—H3A	109.4	O2—C13—H13A	109.3
S2—C3—H3A	109.4	C12—C13—H13A	109.3
O1—C4—C5	122.7 (3)	H13B—C13—H13A	107.9
O1—C4—C3	117.8 (3)	O2—C14—C15	112.5 (3)
C5—C4—C3	119.5 (2)	O2—C14—H14B	109.1
C10—C5—C6	119.0 (3)	C15—C14—H14B	109.1
C10—C5—C4	118.5 (3)	O2—C14—H14A	109.1
C6—C5—C4	122.5 (3)	C15—C14—H14A	109.1
C7—C6—C5	119.9 (3)	H14B—C14—H14A	107.8
C7—C6—H6A	120.0	N4—C15—C14	110.3 (2)
C5—C6—H6A	120.0	N4—C15—H15B	109.6
C8—C7—C6	118.8 (3)	C14—C15—H15B	109.6
C8—C7—H7A	120.6	N4—C15—H15A	109.6
C6—C7—H7A	120.6	C14—C15—H15A	109.6
F1—C8—C9	117.6 (4)	H15B—C15—H15A	108.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···S1	0.98	2.53	3.127 (3)	119
C12—H12A···S2	0.97	2.35	2.881 (3)	114
C12—H12A···N2^i	0.97	2.60	3.283 (4)	128
C15—H15B···S1	0.97	2.59	3.062 (3)	110

Symmetry code: (i) x+1, y, z.