(E)-3-(1,3-Diphenyl-1H-pyrazol-4-yl)-1-(thia­zol-2-yl)prop-2-en-1-one

In the title mol­ecule, C₂₁H₁₅N₃OS, the C5=C6 double bond in the central enone group adopts a trans configuration. The dihedral angle between planes of the thia­zole and pyrazole rings is 6.6 (2)°. In the crystal, pairs of C—H...O hydrogen bonds generate inversion dimers and another pair of C—H...N hydrogen bonds link the dimers into chains propagating along a-axis direction.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.127
• Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -5.826 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.335 Report

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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

(E)-3-(1,3-Diphenyl-1H-pyrazol-4-yl)-1-(thiazol-2-yl)prop-2-en-1-one

Crystal data

C21H15N3OS	F(000) = 744
Mr = 357.42	Dx = 1.339 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.3312 (19) Å	Cell parameters from 5689 reflections
b = 19.124 (4) Å	θ = 2.2–27.4°
c = 9.977 (2) Å	µ = 0.20 mm^−1
β = 95.453 (7)°	T = 223 K
V = 1772.4 (6) Å^3	Block, colourless
Z = 4	0.14 × 0.14 × 0.06 mm

Data collection

Bruker PHOTON III M14 diffractometer	Rint = 0.087
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −12→12
Tmin = 0.673, Tmax = 0.746	k = −25→25
39547 measured reflections	l = −13→13
4419 independent reflections	1 standard reflections every 1 reflections
2775 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0454P)^2 + 0.6998P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4419 reflections	Δρmax = 0.23 e Å^−3
235 parameters	Δρmin = −0.26 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2731 (2)	0.79486 (10)	0.16701 (19)	0.0354 (5)
C2	0.1738 (2)	0.75669 (10)	0.06690 (19)	0.0341 (4)
C3	0.0728 (2)	0.67220 (12)	−0.0560 (2)	0.0479 (6)
H3	0.0573	0.6258	−0.0852	0.058*
C4	−0.0034 (2)	0.72640 (12)	−0.1141 (2)	0.0507 (6)
H4	−0.0760	0.7223	−0.1858	0.061*
C5	0.3616 (2)	0.75244 (11)	0.26503 (19)	0.0344 (4)
H5	0.3527	0.7035	0.2626	0.041*
C6	0.4552 (2)	0.78221 (11)	0.35826 (19)	0.0351 (5)
H6	0.4625	0.8312	0.3574	0.042*
C7	0.5459 (2)	0.74495 (10)	0.45999 (19)	0.0334 (4)
C8	0.6387 (2)	0.77245 (10)	0.56977 (18)	0.0310 (4)
C9	0.5630 (2)	0.67337 (11)	0.4714 (2)	0.0381 (5)
H9	0.5168	0.6396	0.4141	0.046*
C10	0.6660 (2)	0.84560 (10)	0.61250 (19)	0.0319 (4)
C11	0.5555 (2)	0.89512 (11)	0.6078 (2)	0.0377 (5)
H11	0.4613	0.8823	0.5754	0.045*
C12	0.5843 (2)	0.96321 (11)	0.6506 (2)	0.0439 (5)
H12	0.5095	0.9963	0.6462	0.053*
C13	0.7219 (3)	0.98278 (11)	0.6996 (2)	0.0469 (6)
H13	0.7408	1.0290	0.7281	0.056*
C14	0.8320 (2)	0.93384 (12)	0.7065 (2)	0.0469 (5)
H14	0.9256	0.9466	0.7410	0.056*
C15	0.8040 (2)	0.86618 (11)	0.6625 (2)	0.0390 (5)
H15	0.8795	0.8335	0.6665	0.047*
C16	0.7007 (2)	0.59418 (10)	0.6352 (2)	0.0343 (4)
C17	0.6949 (2)	0.53556 (11)	0.5536 (2)	0.0469 (6)
H17	0.6646	0.5396	0.4614	0.056*
C18	0.7338 (3)	0.47096 (11)	0.6082 (2)	0.0508 (6)
H18	0.7297	0.4311	0.5528	0.061*
C19	0.7785 (2)	0.46486 (11)	0.7432 (2)	0.0460 (5)
H19	0.8041	0.4209	0.7804	0.055*
C20	0.7852 (2)	0.52363 (11)	0.8236 (2)	0.0430 (5)
H20	0.8169	0.5195	0.9155	0.052*
C21	0.7461 (2)	0.58883 (10)	0.7711 (2)	0.0368 (5)
H21	0.7502	0.6286	0.8268	0.044*
N1	0.17339 (18)	0.68897 (9)	0.04742 (17)	0.0402 (4)
N2	0.70582 (17)	0.72116 (8)	0.64143 (16)	0.0331 (4)
N3	0.65750 (17)	0.66057 (8)	0.57930 (16)	0.0346 (4)
O1	0.27593 (18)	0.85888 (7)	0.16369 (15)	0.0524 (4)
S1	0.05109 (6)	0.80275 (3)	−0.03886 (6)	0.04908 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0378 (11)	0.0392 (12)	0.0279 (10)	0.0014 (9)	−0.0039 (9)	0.0013 (8)
C2	0.0328 (10)	0.0415 (11)	0.0265 (10)	−0.0015 (8)	−0.0045 (8)	0.0049 (8)
C3	0.0501 (13)	0.0512 (13)	0.0395 (13)	−0.0160 (11)	−0.0110 (10)	0.0025 (10)
C4	0.0437 (13)	0.0643 (15)	0.0406 (13)	−0.0163 (11)	−0.0145 (10)	0.0100 (11)
C5	0.0363 (10)	0.0367 (11)	0.0287 (10)	0.0006 (8)	−0.0046 (8)	−0.0002 (8)
C6	0.0366 (11)	0.0390 (11)	0.0287 (10)	0.0005 (8)	−0.0028 (9)	0.0028 (8)
C7	0.0315 (10)	0.0399 (11)	0.0273 (10)	−0.0008 (8)	−0.0053 (8)	0.0000 (8)
C8	0.0284 (9)	0.0375 (11)	0.0265 (10)	0.0008 (8)	−0.0006 (8)	0.0003 (8)
C9	0.0387 (11)	0.0428 (12)	0.0304 (11)	−0.0017 (9)	−0.0091 (9)	−0.0023 (9)
C10	0.0329 (10)	0.0375 (11)	0.0243 (9)	−0.0009 (8)	−0.0031 (8)	0.0022 (8)
C11	0.0333 (11)	0.0452 (12)	0.0332 (11)	0.0022 (9)	−0.0037 (9)	0.0018 (9)
C12	0.0494 (13)	0.0415 (12)	0.0405 (12)	0.0103 (10)	0.0022 (10)	0.0027 (10)
C13	0.0605 (15)	0.0383 (12)	0.0414 (13)	−0.0072 (10)	0.0023 (11)	−0.0039 (10)
C14	0.0422 (12)	0.0509 (13)	0.0455 (13)	−0.0087 (10)	−0.0063 (10)	−0.0054 (11)
C15	0.0339 (11)	0.0428 (12)	0.0387 (12)	0.0018 (9)	−0.0054 (9)	0.0006 (9)
C16	0.0319 (10)	0.0370 (11)	0.0329 (11)	0.0023 (8)	−0.0027 (8)	0.0000 (8)
C17	0.0585 (14)	0.0443 (13)	0.0355 (12)	0.0063 (11)	−0.0076 (11)	−0.0071 (10)
C18	0.0562 (14)	0.0394 (12)	0.0549 (15)	0.0064 (11)	−0.0044 (12)	−0.0097 (11)
C19	0.0418 (12)	0.0362 (12)	0.0584 (15)	0.0019 (9)	−0.0039 (11)	0.0052 (10)
C20	0.0422 (12)	0.0475 (13)	0.0375 (12)	−0.0017 (10)	−0.0058 (10)	0.0091 (10)
C21	0.0383 (11)	0.0391 (11)	0.0317 (11)	−0.0005 (9)	−0.0034 (9)	−0.0016 (9)
N1	0.0417 (10)	0.0415 (10)	0.0350 (10)	−0.0047 (8)	−0.0079 (8)	0.0026 (8)
N2	0.0339 (9)	0.0344 (9)	0.0294 (9)	0.0003 (7)	−0.0051 (7)	−0.0020 (7)
N3	0.0372 (9)	0.0365 (9)	0.0284 (9)	0.0006 (7)	−0.0064 (7)	−0.0031 (7)
O1	0.0707 (11)	0.0368 (9)	0.0453 (9)	0.0022 (7)	−0.0176 (8)	0.0020 (7)
S1	0.0457 (3)	0.0520 (4)	0.0454 (3)	0.0003 (3)	−0.0178 (3)	0.0110 (3)

Geometric parameters (Å, º)

C1—O1	1.225 (2)	C11—C12	1.389 (3)
C1—C5	1.464 (3)	C11—H11	0.9400
C1—C2	1.488 (3)	C12—C13	1.381 (3)
C2—N1	1.310 (3)	C12—H12	0.9400
C2—S1	1.7235 (19)	C13—C14	1.387 (3)
C3—C4	1.356 (3)	C13—H13	0.9400
C3—N1	1.366 (3)	C14—C15	1.383 (3)
C3—H3	0.9400	C14—H14	0.9400
C4—S1	1.698 (2)	C15—H15	0.9400
C4—H4	0.9400	C16—C17	1.383 (3)
C5—C6	1.341 (3)	C16—C21	1.386 (3)
C5—H5	0.9400	C16—N3	1.429 (2)
C6—C7	1.446 (3)	C17—C18	1.384 (3)
C6—H6	0.9400	C17—H17	0.9400
C7—C9	1.382 (3)	C18—C19	1.377 (3)
C7—C8	1.430 (2)	C18—H18	0.9400
C8—N2	1.334 (2)	C19—C20	1.379 (3)
C8—C10	1.478 (3)	C19—H19	0.9400
C9—N3	1.348 (2)	C20—C21	1.388 (3)
C9—H9	0.9400	C20—H20	0.9400
C10—C15	1.393 (3)	C21—H21	0.9400
C10—C11	1.397 (3)	N2—N3	1.370 (2)
O1—C1—C5	124.01 (18)	C11—C12—H12	119.7
O1—C1—C2	119.07 (17)	C12—C13—C14	119.6 (2)
C5—C1—C2	116.91 (17)	C12—C13—H13	120.2
N1—C2—C1	125.29 (17)	C14—C13—H13	120.2
N1—C2—S1	114.98 (14)	C15—C14—C13	119.9 (2)
C1—C2—S1	119.70 (15)	C15—C14—H14	120.0
C4—C3—N1	116.0 (2)	C13—C14—H14	120.0
C4—C3—H3	122.0	C14—C15—C10	121.2 (2)
N1—C3—H3	122.0	C14—C15—H15	119.4
C3—C4—S1	110.21 (17)	C10—C15—H15	119.4
C3—C4—H4	124.9	C17—C16—C21	120.48 (19)
S1—C4—H4	124.9	C17—C16—N3	119.78 (18)
C6—C5—C1	121.15 (19)	C21—C16—N3	119.73 (17)
C6—C5—H5	119.4	C16—C17—C18	119.9 (2)
C1—C5—H5	119.4	C16—C17—H17	120.1
C5—C6—C7	125.23 (19)	C18—C17—H17	120.1
C5—C6—H6	117.4	C19—C18—C17	120.2 (2)
C7—C6—H6	117.4	C19—C18—H18	119.9
C9—C7—C8	104.15 (16)	C17—C18—H18	119.9
C9—C7—C6	126.98 (18)	C18—C19—C20	119.5 (2)
C8—C7—C6	128.87 (18)	C18—C19—H19	120.2
N2—C8—C7	111.06 (17)	C20—C19—H19	120.2
N2—C8—C10	118.81 (16)	C19—C20—C21	121.1 (2)
C7—C8—C10	130.13 (17)	C19—C20—H20	119.4
N3—C9—C7	107.91 (17)	C21—C20—H20	119.4
N3—C9—H9	126.0	C16—C21—C20	118.71 (19)
C7—C9—H9	126.0	C16—C21—H21	120.6
C15—C10—C11	118.33 (18)	C20—C21—H21	120.6
C15—C10—C8	119.95 (17)	C2—N1—C3	109.66 (18)
C11—C10—C8	121.69 (17)	C8—N2—N3	105.17 (15)
C12—C11—C10	120.31 (19)	C9—N3—N2	111.72 (16)
C12—C11—H11	119.8	C9—N3—C16	127.74 (16)
C10—C11—H11	119.8	N2—N3—C16	120.41 (15)
C13—C12—C11	120.6 (2)	C4—S1—C2	89.14 (10)
C13—C12—H12	119.7
O1—C1—C2—N1	170.4 (2)	C11—C10—C15—C14	−0.1 (3)
C5—C1—C2—N1	−10.0 (3)	C8—C10—C15—C14	−178.33 (19)
O1—C1—C2—S1	−7.2 (3)	C21—C16—C17—C18	0.4 (3)
C5—C1—C2—S1	172.39 (15)	N3—C16—C17—C18	−178.6 (2)
N1—C3—C4—S1	0.3 (3)	C16—C17—C18—C19	−0.1 (4)
O1—C1—C5—C6	−1.0 (3)	C17—C18—C19—C20	−0.5 (4)
C2—C1—C5—C6	179.36 (19)	C18—C19—C20—C21	0.8 (3)
C1—C5—C6—C7	179.25 (19)	C17—C16—C21—C20	−0.1 (3)
C5—C6—C7—C9	6.8 (3)	N3—C16—C21—C20	178.92 (18)
C5—C6—C7—C8	−173.9 (2)	C19—C20—C21—C16	−0.5 (3)
C9—C7—C8—N2	−0.1 (2)	C1—C2—N1—C3	−177.27 (19)
C6—C7—C8—N2	−179.51 (19)	S1—C2—N1—C3	0.4 (2)
C9—C7—C8—C10	−179.0 (2)	C4—C3—N1—C2	−0.5 (3)
C6—C7—C8—C10	1.5 (3)	C7—C8—N2—N3	0.0 (2)
C8—C7—C9—N3	0.2 (2)	C10—C8—N2—N3	179.03 (16)
C6—C7—C9—N3	179.63 (19)	C7—C9—N3—N2	−0.2 (2)
N2—C8—C10—C15	38.3 (3)	C7—C9—N3—C16	175.49 (18)
C7—C8—C10—C15	−142.9 (2)	C8—N2—N3—C9	0.2 (2)
N2—C8—C10—C11	−139.93 (19)	C8—N2—N3—C16	−175.91 (17)
C7—C8—C10—C11	38.9 (3)	C17—C16—N3—C9	26.8 (3)
C15—C10—C11—C12	0.8 (3)	C21—C16—N3—C9	−152.2 (2)
C8—C10—C11—C12	179.01 (18)	C17—C16—N3—N2	−157.79 (19)
C10—C11—C12—C13	−0.6 (3)	C21—C16—N3—N2	23.2 (3)
C11—C12—C13—C14	−0.2 (3)	C3—C4—S1—C2	−0.04 (19)
C12—C13—C14—C15	0.9 (3)	N1—C2—S1—C4	−0.24 (17)
C13—C14—C15—C10	−0.8 (3)	C1—C2—S1—C4	177.61 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1^i	0.94	2.56	3.451 (3)	158
C4—H4···N2^ii	0.94	2.54	3.473 (3)	172
C13—H13···O1^iii	0.94	2.41	3.321 (3)	162

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