5-(4-Fluoro­benzyl­amino)-3,6-diphenyl-2-thioxo-2,3-dihydro-1,3-thia­zolo[4,5-d]pyrimidin-7(6H)-one

In the title compound, C₂₄H₁₇FN₄OS₂, the three benzene rings are twisted with respect to the fused heterocyclic ring system, with dihedral angles of 76.2 (2), 90.2 (2) and 75.8 (2)°. The crystal packing is influenced by C—H...O, N—H...O and C—H...S hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.053
• wR factor = 0.176
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3      ..       6.27 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C23
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C12    -C17           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT731_ALERT_1_C Bond    Calc     0.84(6), Rep     0.84(2) ......       3.00 su-Rat
              N4   -H4A     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(6), Rep     0.84(2) ......       3.00 su-Rat
              N4   -H4A     1.555   1.555

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           27.00
           From the CIF: _reflns_number_total               3862
           Count of symmetry unique reflns         2601
           Completeness (_total/calc)            148.48%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1261
           Fraction of Friedel pairs measured     0.485
           Are heavy atom types Z>Si present        yes

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

5-(4-Fluorobenzylamino)-3,6-diphenyl-2-thioxo-2,3-dihydro-1,3- thiazolo[4,5-d]pyrimidin-7(6H)-one

Crystal data

C24H17FN4OS2	F(000) = 476
Mr = 460.54	Dx = 1.368 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2435 reflections
a = 10.4507 (14) Å	θ = 2.8–23.0°
b = 9.2317 (12) Å	µ = 0.27 mm^−1
c = 11.9817 (16) Å	T = 292 K
β = 104.691 (2)°	Block, colorless
V = 1118.2 (3) Å^3	0.30 × 0.20 × 0.10 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	3279 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 27.0°, θmin = 1.8°
φ and ω scans	h = −12→13
6576 measured reflections	k = −10→11
3862 independent reflections	l = −14→15

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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.176	w = 1/[σ^2(Fo^2) + (0.1174P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3862 reflections	Δρmax = 0.25 e Å^−3
292 parameters	Δρmin = −0.31 e Å^−3
8 restraints	Absolute structure: Flack (1983), 1261 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (12)

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
C1	0.5572 (4)	0.6485 (5)	0.6529 (3)	0.0560 (9)
H1	0.6413	0.6889	0.6764	0.067*
C2	0.4600 (6)	0.6823 (6)	0.7092 (4)	0.0714 (13)
H2	0.4783	0.7482	0.7699	0.086*
C3	0.3379 (5)	0.6195 (6)	0.6762 (4)	0.0668 (12)
H3	0.2748	0.6405	0.7163	0.080*
C4	0.3078 (4)	0.5266 (5)	0.5851 (4)	0.0637 (11)
H4	0.2239	0.4856	0.5626	0.076*
C5	0.4021 (4)	0.4929 (5)	0.5258 (3)	0.0521 (9)
H5	0.3819	0.4304	0.4629	0.063*
C6	0.5256 (3)	0.5537 (4)	0.5616 (3)	0.0428 (7)
C7	0.7277 (4)	0.4204 (4)	0.5495 (3)	0.0487 (8)
C8	0.6181 (3)	0.5866 (4)	0.3944 (3)	0.0411 (7)
C9	0.7993 (3)	0.4706 (4)	0.3777 (3)	0.0438 (8)
C10	0.8200 (4)	0.4050 (4)	0.4823 (3)	0.0495 (8)
C11	0.9868 (4)	0.3341 (5)	0.3758 (4)	0.0607 (10)
C12	0.8860 (4)	0.4802 (5)	0.2024 (3)	0.0495 (9)
C13	0.8190 (5)	0.4032 (6)	0.1092 (4)	0.0738 (13)
H13	0.7762	0.3172	0.1178	0.089*
C14	0.8169 (6)	0.4573 (9)	0.0006 (4)	0.0912 (19)
H14	0.7708	0.4056	−0.0637	0.109*
C15	0.8762 (5)	0.5772 (8)	−0.0161 (4)	0.0823 (16)
H15	0.8718	0.6101	−0.0903	0.099*
C16	0.9455 (7)	0.6537 (7)	0.0792 (5)	0.0922 (18)
H16	0.9868	0.7401	0.0689	0.111*
C17	0.9542 (5)	0.6036 (6)	0.1892 (4)	0.0700 (12)
H17	1.0051	0.6523	0.2531	0.084*
C18	0.4995 (4)	0.7477 (4)	0.2425 (3)	0.0458 (8)
H18A	0.5847	0.7775	0.2320	0.055*
H18B	0.4453	0.8337	0.2391	0.055*
C19	0.4344 (4)	0.6471 (4)	0.1463 (3)	0.0483 (8)
C20	0.4986 (5)	0.6071 (4)	0.0622 (3)	0.0568 (10)
H20	0.5835	0.6411	0.0664	0.068*
C21	0.4366 (5)	0.5173 (6)	−0.0272 (4)	0.0712 (13)
H21	0.4796	0.4903	−0.0830	0.085*
C22	0.3158 (5)	0.4700 (6)	−0.0331 (4)	0.0712 (13)
C23	0.2497 (6)	0.5011 (8)	0.0495 (5)	0.096 (2)
H23	0.1662	0.4634	0.0457	0.115*
C24	0.3136 (5)	0.5916 (7)	0.1391 (4)	0.0768 (14)
H24	0.2711	0.6147	0.1963	0.092*
F1	0.2537 (4)	0.3839 (5)	−0.1226 (3)	0.1084 (12)
N1	0.6254 (3)	0.5206 (3)	0.4992 (2)	0.0426 (7)
N2	0.7001 (3)	0.5615 (3)	0.3300 (2)	0.0431 (6)
N3	0.8914 (3)	0.4306 (4)	0.3182 (3)	0.0488 (7)
N4	0.5184 (3)	0.6804 (4)	0.3553 (2)	0.0490 (7)
O1	0.7259 (3)	0.3570 (4)	0.6381 (3)	0.0689 (9)
S1	0.95765 (10)	0.29361 (14)	0.50878 (10)	0.0655 (3)
S2	1.10812 (13)	0.2661 (2)	0.32928 (13)	0.0945 (6)
H4A	0.459 (5)	0.696 (8)	0.390 (5)	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.061 (2)	0.061 (2)	0.0508 (19)	−0.013 (2)	0.0235 (17)	0.0014 (17)
C2	0.102 (4)	0.065 (3)	0.058 (2)	0.007 (3)	0.041 (2)	−0.002 (2)
C3	0.059 (3)	0.078 (3)	0.076 (3)	0.013 (2)	0.041 (2)	0.015 (2)
C4	0.040 (2)	0.073 (3)	0.086 (3)	0.000 (2)	0.031 (2)	0.014 (2)
C5	0.045 (2)	0.060 (2)	0.056 (2)	−0.0030 (18)	0.0192 (16)	0.0044 (17)
C6	0.0416 (18)	0.0461 (18)	0.0462 (17)	−0.0004 (15)	0.0215 (14)	0.0085 (14)
C7	0.0411 (19)	0.054 (2)	0.0543 (19)	0.0002 (16)	0.0177 (15)	0.0127 (16)
C8	0.0429 (18)	0.0404 (17)	0.0420 (16)	−0.0020 (14)	0.0147 (13)	0.0000 (13)
C9	0.0387 (17)	0.0477 (18)	0.0479 (18)	−0.0031 (14)	0.0165 (14)	−0.0014 (14)
C10	0.0385 (18)	0.056 (2)	0.055 (2)	0.0045 (16)	0.0141 (15)	0.0107 (16)
C11	0.047 (2)	0.070 (3)	0.067 (2)	0.0100 (19)	0.0174 (18)	0.0097 (19)
C12	0.0392 (18)	0.064 (2)	0.0521 (19)	0.0096 (17)	0.0242 (15)	0.0037 (17)
C13	0.072 (3)	0.082 (3)	0.067 (3)	−0.012 (3)	0.017 (2)	−0.006 (2)
C14	0.085 (4)	0.131 (6)	0.056 (3)	0.012 (4)	0.015 (2)	−0.004 (3)
C15	0.072 (3)	0.123 (5)	0.061 (3)	0.027 (3)	0.035 (2)	0.020 (3)
C16	0.116 (5)	0.078 (4)	0.102 (4)	0.009 (4)	0.065 (4)	0.025 (3)
C17	0.078 (3)	0.075 (3)	0.067 (3)	−0.004 (2)	0.037 (2)	−0.003 (2)
C18	0.056 (2)	0.0423 (18)	0.0447 (17)	0.0083 (16)	0.0234 (15)	0.0045 (14)
C19	0.051 (2)	0.0480 (19)	0.0483 (18)	0.0118 (16)	0.0176 (15)	0.0048 (15)
C20	0.073 (3)	0.054 (2)	0.0500 (19)	0.0018 (19)	0.0288 (19)	−0.0023 (17)
C21	0.087 (3)	0.078 (3)	0.058 (2)	0.001 (3)	0.036 (2)	−0.010 (2)
C22	0.074 (3)	0.073 (3)	0.068 (3)	−0.003 (2)	0.021 (2)	−0.021 (2)
C23	0.084 (4)	0.107 (5)	0.109 (4)	−0.024 (4)	0.047 (3)	−0.042 (4)
C24	0.063 (3)	0.096 (4)	0.082 (3)	−0.002 (3)	0.036 (2)	−0.030 (3)
F1	0.106 (3)	0.122 (3)	0.099 (2)	−0.028 (2)	0.030 (2)	−0.052 (2)
N1	0.0359 (14)	0.0528 (17)	0.0432 (14)	−0.0029 (13)	0.0176 (11)	0.0039 (12)
N2	0.0422 (16)	0.0493 (16)	0.0426 (13)	0.0046 (13)	0.0198 (12)	0.0042 (13)
N3	0.0348 (15)	0.0584 (18)	0.0577 (17)	0.0068 (14)	0.0202 (13)	0.0058 (14)
N4	0.0577 (19)	0.0529 (17)	0.0439 (14)	0.0148 (15)	0.0269 (13)	0.0060 (13)
O1	0.0683 (19)	0.082 (2)	0.0623 (17)	0.0074 (17)	0.0283 (15)	0.0339 (15)
S1	0.0420 (5)	0.0864 (8)	0.0705 (6)	0.0165 (5)	0.0185 (4)	0.0268 (6)
S2	0.0656 (8)	0.1293 (14)	0.0974 (9)	0.0481 (9)	0.0369 (7)	0.0185 (9)

Geometric parameters (Å, º)

C1—C6	1.375 (6)	C12—N3	1.448 (5)
C1—C2	1.389 (6)	C13—C14	1.389 (8)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.365 (7)	C14—C15	1.308 (10)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.360 (7)	C15—C16	1.380 (9)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.389 (6)	C16—C17	1.378 (7)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.372 (5)	C17—H17	0.9300
C5—H5	0.9300	C18—N4	1.455 (4)
C6—N1	1.462 (4)	C18—C19	1.502 (5)
C7—O1	1.216 (4)	C18—H18A	0.9700
C7—C10	1.411 (5)	C18—H18B	0.9700
C7—N1	1.426 (5)	C19—C24	1.345 (7)
C8—N2	1.311 (4)	C19—C20	1.394 (5)
C8—N4	1.344 (5)	C20—C21	1.379 (6)
C8—N1	1.381 (4)	C20—H20	0.9300
C9—N2	1.343 (5)	C21—C22	1.321 (7)
C9—C10	1.359 (5)	C21—H21	0.9300
C9—N3	1.385 (4)	C22—F1	1.360 (6)
C10—S1	1.731 (4)	C22—C23	1.373 (7)
C11—N3	1.384 (5)	C23—C24	1.391 (8)
C11—S2	1.634 (4)	C23—H23	0.9300
C11—S1	1.737 (4)	C24—H24	0.9300
C12—C13	1.359 (6)	N4—H4A	0.84 (2)
C12—C17	1.375 (6)
C6—C1—C2	118.1 (4)	C14—C15—H15	120.8
C6—C1—H1	120.9	C16—C15—H15	120.8
C2—C1—H1	120.9	C17—C16—C15	120.9 (6)
C3—C2—C1	120.6 (4)	C17—C16—H16	119.6
C3—C2—H2	119.7	C15—C16—H16	119.6
C1—C2—H2	119.7	C12—C17—C16	118.5 (5)
C4—C3—C2	120.6 (4)	C12—C17—H17	120.7
C4—C3—H3	119.7	C16—C17—H17	120.7
C2—C3—H3	119.7	N4—C18—C19	112.2 (3)
C3—C4—C5	120.1 (4)	N4—C18—H18A	109.2
C3—C4—H4	119.9	C19—C18—H18A	109.2
C5—C4—H4	119.9	N4—C18—H18B	109.2
C6—C5—C4	118.8 (4)	C19—C18—H18B	109.2
C6—C5—H5	120.6	H18A—C18—H18B	107.9
C4—C5—H5	120.6	C24—C19—C20	118.0 (4)
C5—C6—C1	121.8 (3)	C24—C19—C18	121.3 (3)
C5—C6—N1	119.4 (3)	C20—C19—C18	120.7 (4)
C1—C6—N1	118.8 (3)	C21—C20—C19	120.1 (4)
O1—C7—C10	127.8 (4)	C21—C20—H20	119.9
O1—C7—N1	120.3 (3)	C19—C20—H20	119.9
C10—C7—N1	111.8 (3)	C22—C21—C20	119.7 (4)
N2—C8—N4	118.3 (3)	C22—C21—H21	120.1
N2—C8—N1	124.3 (3)	C20—C21—H21	120.1
N4—C8—N1	117.4 (3)	C21—C22—F1	119.6 (4)
N2—C9—C10	126.6 (3)	C21—C22—C23	122.7 (5)
N2—C9—N3	120.6 (3)	F1—C22—C23	117.7 (5)
C10—C9—N3	112.7 (3)	C22—C23—C24	116.8 (5)
C9—C10—C7	120.6 (3)	C22—C23—H23	121.6
C9—C10—S1	111.4 (3)	C24—C23—H23	121.6
C7—C10—S1	127.7 (3)	C19—C24—C23	122.5 (4)
N3—C11—S2	126.9 (3)	C19—C24—H24	118.8
N3—C11—S1	108.9 (3)	C23—C24—H24	118.8
S2—C11—S1	124.2 (3)	C8—N1—C7	122.2 (3)
C13—C12—C17	120.8 (4)	C8—N1—C6	119.4 (3)
C13—C12—N3	120.6 (4)	C7—N1—C6	118.4 (3)
C17—C12—N3	118.5 (4)	C8—N2—C9	114.1 (3)
C12—C13—C14	117.7 (5)	C11—N3—C9	115.0 (3)
C12—C13—H13	121.1	C11—N3—C12	121.9 (3)
C14—C13—H13	121.1	C9—N3—C12	123.0 (3)
C15—C14—C13	123.5 (6)	C8—N4—C18	120.6 (3)
C15—C14—H14	118.3	C8—N4—H4A	123 (5)
C13—C14—H14	118.3	C18—N4—H4A	116 (5)
C14—C15—C16	118.4 (5)	C10—S1—C11	92.01 (19)
C6—C1—C2—C3	1.8 (7)	N2—C8—N1—C7	2.1 (5)
C1—C2—C3—C4	−2.3 (7)	N4—C8—N1—C7	−179.4 (3)
C2—C3—C4—C5	1.0 (7)	N2—C8—N1—C6	−178.0 (3)
C3—C4—C5—C6	0.7 (6)	N4—C8—N1—C6	0.6 (5)
C4—C5—C6—C1	−1.2 (6)	O1—C7—N1—C8	−175.0 (4)
C4—C5—C6—N1	−179.3 (4)	C10—C7—N1—C8	2.9 (5)
C2—C1—C6—C5	0.0 (6)	O1—C7—N1—C6	5.0 (6)
C2—C1—C6—N1	178.1 (4)	C10—C7—N1—C6	−177.0 (3)
N2—C9—C10—C7	4.9 (6)	C5—C6—N1—C8	76.6 (4)
N3—C9—C10—C7	−173.0 (4)	C1—C6—N1—C8	−101.6 (4)
N2—C9—C10—S1	178.8 (3)	C5—C6—N1—C7	−103.4 (4)
N3—C9—C10—S1	0.9 (4)	C1—C6—N1—C7	78.4 (4)
O1—C7—C10—C9	171.8 (4)	N4—C8—N2—C9	177.7 (3)
N1—C7—C10—C9	−6.0 (5)	N1—C8—N2—C9	−3.7 (5)
O1—C7—C10—S1	−1.0 (7)	C10—C9—N2—C8	0.3 (6)
N1—C7—C10—S1	−178.8 (3)	N3—C9—N2—C8	178.0 (3)
C17—C12—C13—C14	−3.0 (7)	S2—C11—N3—C9	179.8 (4)
N3—C12—C13—C14	179.5 (5)	S1—C11—N3—C9	0.1 (5)
C12—C13—C14—C15	0.4 (9)	S2—C11—N3—C12	2.3 (6)
C13—C14—C15—C16	0.5 (9)	S1—C11—N3—C12	−177.3 (3)
C14—C15—C16—C17	1.2 (9)	N2—C9—N3—C11	−178.7 (4)
C13—C12—C17—C16	4.6 (7)	C10—C9—N3—C11	−0.7 (5)
N3—C12—C17—C16	−177.8 (4)	N2—C9—N3—C12	−1.3 (6)
C15—C16—C17—C12	−3.7 (9)	C10—C9—N3—C12	176.7 (4)
N4—C18—C19—C24	60.0 (5)	C13—C12—N3—C11	86.8 (5)
N4—C18—C19—C20	−119.2 (4)	C17—C12—N3—C11	−90.7 (5)
C24—C19—C20—C21	2.2 (6)	C13—C12—N3—C9	−90.4 (5)
C18—C19—C20—C21	−178.5 (4)	C17—C12—N3—C9	92.1 (5)
C19—C20—C21—C22	0.3 (7)	N2—C8—N4—C18	2.4 (5)
C20—C21—C22—F1	178.6 (5)	N1—C8—N4—C18	−176.3 (3)
C20—C21—C22—C23	−2.9 (9)	C19—C18—N4—C8	78.2 (4)
C21—C22—C23—C24	2.8 (10)	C9—C10—S1—C11	−0.7 (3)
F1—C22—C23—C24	−178.7 (6)	C7—C10—S1—C11	172.7 (4)
C20—C19—C24—C23	−2.3 (8)	N3—C11—S1—C10	0.3 (3)
C18—C19—C24—C23	178.4 (5)	S2—C11—S1—C10	−179.3 (4)
C22—C23—C24—C19	−0.1 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O1^i	0.97	2.60	3.213 (5)	122
C1—H1···S2^ii	0.93	2.73	3.616 (4)	159
N4—H4A···O1^i	0.84 (2)	2.39 (5)	3.047 (5)	135 (6)

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+2, y+1/2, −z+1.