4-(4-Methoxy­benzo­yl)-2,2-dimethyl-5-phenyl­amino-2,3-dihydro-1,3,4-thia­diazole

In the title compound, C₁₈H₁₉N₃O₂S, the thia­diazole ring adopts an envelope conformation. The crystal structure is stabilized by inter­molecular N—H...O hydrogen bonds, forming one-dimensional chains parallel to the b axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.063
• wR factor = 0.124
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

   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

   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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

4-(4-Methoxybenzoyl)-2,2-dimethyl-5-phenylamino-2,3-dihydro-1,3,4-thiadiazole

Crystal data

C18H19N3O2S	F(000) = 1440
Mr = 341.42	Dx = 1.336 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2397 reflections
a = 9.4042 (14) Å	θ = 1.7–25.2°
b = 15.603 (2) Å	µ = 0.21 mm^−1
c = 23.143 (4) Å	T = 298 K
V = 3395.8 (9) Å^3	Block, colourless
Z = 8	0.48 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3073 independent reflections
Radiation source: fine-focus sealed tube	2446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 83.66 pixels mm^-1	θmax = 25.2°, θmin = 1.7°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −18→18
Tmin = 0.907, Tmax = 0.960	l = −18→27
16783 measured reflections

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.25	w = 1/[σ^2(Fo^2) + (0.0359P)^2 + 2.015P] where P = (Fo^2 + 2Fc^2)/3
3073 reflections	(Δ/σ)max < 0.001
224 parameters	Δρmax = 0.19 e Å^−3
1 restraint	Δρmin = −0.25 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.95754 (9)	0.18140 (4)	0.29183 (3)	0.0434 (2)
O1	0.9255 (2)	0.46800 (12)	0.30248 (9)	0.0465 (6)
O2	0.8325 (2)	0.55427 (14)	0.03674 (9)	0.0540 (6)
N1	1.0452 (3)	0.15321 (14)	0.18271 (10)	0.0370 (6)
H1B	1.063 (3)	0.1034 (9)	0.1951 (11)	0.037 (8)*
N2	1.0238 (3)	0.29451 (13)	0.21392 (9)	0.0366 (6)
N3	0.9840 (3)	0.33988 (13)	0.26382 (9)	0.0343 (6)
C1	1.1747 (3)	0.11211 (19)	0.09827 (13)	0.0463 (8)
H1	1.2084	0.0647	0.1184	0.056*
C2	1.2146 (4)	0.1250 (2)	0.04176 (14)	0.0597 (10)
H2	1.2751	0.0860	0.0239	0.072*
C3	1.1659 (4)	0.1949 (2)	0.01137 (14)	0.0626 (10)
H3	1.1938	0.2037	−0.0267	0.075*
C4	1.0758 (4)	0.2512 (2)	0.03810 (14)	0.0538 (9)
H4	1.0418	0.2983	0.0176	0.065*
C5	1.0345 (3)	0.23986 (18)	0.09450 (13)	0.0432 (8)
H5	0.9734	0.2789	0.1120	0.052*
C6	1.0848 (3)	0.16949 (16)	0.12513 (12)	0.0349 (7)
C7	1.0146 (3)	0.21353 (16)	0.22344 (11)	0.0323 (6)
C8	0.9995 (3)	0.29014 (17)	0.31795 (12)	0.0342 (7)
C9	0.9469 (3)	0.42353 (15)	0.25918 (12)	0.0326 (7)
C10	0.9249 (3)	0.45955 (15)	0.19985 (12)	0.0324 (7)
C11	1.0191 (3)	0.45278 (17)	0.15439 (13)	0.0404 (7)
H11	1.1058	0.4253	0.1599	0.049*
C12	0.9865 (3)	0.48620 (18)	0.10097 (13)	0.0436 (8)
H12	1.0515	0.4819	0.0708	0.052*
C13	0.8566 (3)	0.52638 (17)	0.09204 (13)	0.0385 (7)
C14	0.7636 (3)	0.53593 (18)	0.13717 (13)	0.0418 (7)
H14	0.6774	0.5641	0.1317	0.050*
C15	0.7986 (3)	0.50347 (17)	0.19088 (13)	0.0387 (7)
H15	0.7363	0.5113	0.2216	0.046*
C16	0.6954 (4)	0.5854 (3)	0.02343 (16)	0.0726 (11)
H16A	0.6258	0.5428	0.0334	0.109*
H16B	0.6896	0.5976	−0.0172	0.109*
H16C	0.6775	0.6368	0.0450	0.109*
C17	0.8926 (4)	0.31297 (19)	0.36469 (13)	0.0519 (9)
H17A	0.9164	0.3677	0.3809	0.078*
H17B	0.8949	0.2702	0.3945	0.078*
H17C	0.7990	0.3154	0.3482	0.078*
C18	1.1516 (3)	0.2929 (2)	0.33883 (14)	0.0531 (9)
H18A	1.2141	0.2768	0.3079	0.080*
H18B	1.1632	0.2538	0.3705	0.080*
H18C	1.1742	0.3500	0.3514	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0616 (6)	0.0274 (4)	0.0413 (5)	−0.0051 (4)	0.0083 (4)	0.0022 (3)
O1	0.0654 (15)	0.0286 (11)	0.0456 (13)	0.0047 (10)	0.0038 (11)	−0.0079 (9)
O2	0.0567 (15)	0.0627 (14)	0.0426 (14)	0.0148 (11)	0.0019 (11)	0.0103 (11)
N1	0.0520 (16)	0.0209 (12)	0.0381 (14)	0.0030 (11)	0.0011 (12)	0.0010 (11)
N2	0.0520 (16)	0.0236 (11)	0.0341 (13)	0.0022 (11)	0.0041 (12)	−0.0012 (10)
N3	0.0456 (15)	0.0254 (11)	0.0320 (14)	0.0037 (10)	0.0050 (11)	−0.0010 (10)
C1	0.060 (2)	0.0325 (16)	0.046 (2)	0.0054 (15)	0.0021 (16)	−0.0030 (14)
C2	0.080 (3)	0.053 (2)	0.046 (2)	0.0072 (19)	0.0136 (19)	−0.0084 (17)
C3	0.086 (3)	0.065 (2)	0.0366 (19)	−0.003 (2)	0.0084 (19)	0.0016 (17)
C4	0.068 (2)	0.051 (2)	0.042 (2)	−0.0037 (18)	−0.0111 (18)	0.0091 (16)
C5	0.050 (2)	0.0360 (16)	0.0432 (19)	−0.0002 (15)	−0.0082 (15)	−0.0007 (13)
C6	0.0422 (18)	0.0271 (14)	0.0353 (16)	−0.0052 (12)	−0.0048 (13)	−0.0028 (12)
C7	0.0346 (17)	0.0261 (14)	0.0361 (16)	−0.0007 (12)	−0.0015 (13)	0.0023 (12)
C8	0.0401 (17)	0.0267 (14)	0.0358 (16)	−0.0001 (12)	0.0037 (13)	0.0006 (12)
C9	0.0320 (16)	0.0237 (13)	0.0422 (18)	−0.0020 (12)	0.0019 (14)	−0.0017 (12)
C10	0.0373 (17)	0.0198 (13)	0.0400 (17)	−0.0010 (11)	0.0022 (14)	0.0001 (11)
C11	0.0365 (18)	0.0299 (15)	0.055 (2)	0.0062 (13)	0.0073 (15)	0.0078 (14)
C12	0.0456 (19)	0.0368 (16)	0.0483 (19)	0.0054 (14)	0.0159 (15)	0.0068 (14)
C13	0.0452 (19)	0.0288 (15)	0.0414 (18)	0.0010 (13)	0.0012 (15)	0.0016 (13)
C14	0.0370 (18)	0.0403 (17)	0.0481 (19)	0.0100 (13)	−0.0008 (15)	0.0027 (15)
C15	0.0371 (18)	0.0341 (16)	0.0449 (18)	0.0040 (13)	0.0075 (14)	−0.0032 (13)
C16	0.077 (3)	0.083 (3)	0.058 (2)	0.027 (2)	−0.010 (2)	0.013 (2)
C17	0.069 (2)	0.0397 (17)	0.0472 (19)	0.0022 (16)	0.0190 (17)	0.0022 (15)
C18	0.053 (2)	0.056 (2)	0.051 (2)	−0.0067 (17)	−0.0086 (17)	0.0001 (16)

Geometric parameters (Å, º)

S1—C7	1.745 (3)	C8—C18	1.510 (4)
S1—C8	1.844 (3)	C8—C17	1.519 (4)
O1—C9	1.235 (3)	C9—C10	1.498 (4)
O2—C13	1.371 (3)	C10—C11	1.380 (4)
O2—C16	1.412 (4)	C10—C15	1.386 (4)
N1—C7	1.363 (3)	C11—C12	1.376 (4)
N1—C6	1.407 (4)	C11—H11	0.9300
N1—H1B	0.844 (10)	C12—C13	1.389 (4)
N2—C7	1.286 (3)	C12—H12	0.9300
N2—N3	1.405 (3)	C13—C14	1.371 (4)
N3—C9	1.355 (3)	C14—C15	1.382 (4)
N3—C8	1.481 (3)	C14—H14	0.9300
C1—C2	1.375 (4)	C15—H15	0.9300
C1—C6	1.379 (4)	C16—H16A	0.9600
C1—H1	0.9300	C16—H16B	0.9600
C2—C3	1.376 (5)	C16—H16C	0.9600
C2—H2	0.9300	C17—H17A	0.9600
C3—C4	1.369 (5)	C17—H17B	0.9600
C3—H3	0.9300	C17—H17C	0.9600
C4—C5	1.373 (4)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.390 (4)	C18—H18C	0.9600
C5—H5	0.9300
C7—S1—C8	88.11 (12)	N3—C9—C10	118.0 (2)
C13—O2—C16	117.6 (3)	C11—C10—C15	118.3 (3)
C7—N1—C6	125.9 (2)	C11—C10—C9	125.5 (3)
C7—N1—H1B	116.2 (19)	C15—C10—C9	116.2 (2)
C6—N1—H1B	115.9 (19)	C12—C11—C10	120.9 (3)
C7—N2—N3	109.6 (2)	C12—C11—H11	119.6
C9—N3—N2	119.3 (2)	C10—C11—H11	119.6
C9—N3—C8	126.7 (2)	C11—C12—C13	120.1 (3)
N2—N3—C8	113.9 (2)	C11—C12—H12	120.0
C2—C1—C6	120.1 (3)	C13—C12—H12	120.0
C2—C1—H1	120.0	O2—C13—C14	124.9 (3)
C6—C1—H1	120.0	O2—C13—C12	115.3 (3)
C1—C2—C3	120.7 (3)	C14—C13—C12	119.8 (3)
C1—C2—H2	119.6	C13—C14—C15	119.6 (3)
C3—C2—H2	119.6	C13—C14—H14	120.2
C4—C3—C2	118.9 (3)	C15—C14—H14	120.2
C4—C3—H3	120.5	C14—C15—C10	121.3 (3)
C2—C3—H3	120.5	C14—C15—H15	119.3
C3—C4—C5	121.4 (3)	C10—C15—H15	119.3
C3—C4—H4	119.3	O2—C16—H16A	109.5
C5—C4—H4	119.3	O2—C16—H16B	109.5
C4—C5—C6	119.4 (3)	H16A—C16—H16B	109.5
C4—C5—H5	120.3	O2—C16—H16C	109.5
C6—C5—H5	120.3	H16A—C16—H16C	109.5
C1—C6—C5	119.4 (3)	H16B—C16—H16C	109.5
C1—C6—N1	118.2 (2)	C8—C17—H17A	109.5
C5—C6—N1	122.4 (3)	C8—C17—H17B	109.5
N2—C7—N1	123.1 (3)	H17A—C17—H17B	109.5
N2—C7—S1	117.3 (2)	C8—C17—H17C	109.5
N1—C7—S1	119.60 (19)	H17A—C17—H17C	109.5
N3—C8—C18	110.4 (2)	H17B—C17—H17C	109.5
N3—C8—C17	114.5 (2)	C8—C18—H18A	109.5
C18—C8—C17	113.1 (3)	C8—C18—H18B	109.5
N3—C8—S1	100.59 (17)	H18A—C18—H18B	109.5
C18—C8—S1	109.5 (2)	C8—C18—H18C	109.5
C17—C8—S1	107.9 (2)	H18A—C18—H18C	109.5
O1—C9—N3	121.2 (3)	H18B—C18—H18C	109.5
O1—C9—C10	120.7 (2)
C7—N2—N3—C9	−161.4 (3)	C7—S1—C8—N3	26.20 (18)
C7—N2—N3—C8	23.5 (3)	C7—S1—C8—C18	−90.1 (2)
C6—C1—C2—C3	0.1 (5)	C7—S1—C8—C17	146.4 (2)
C1—C2—C3—C4	−0.6 (6)	N2—N3—C9—O1	−172.4 (2)
C2—C3—C4—C5	0.7 (5)	C8—N3—C9—O1	2.0 (4)
C3—C4—C5—C6	−0.2 (5)	N2—N3—C9—C10	10.8 (4)
C2—C1—C6—C5	0.4 (5)	C8—N3—C9—C10	−174.7 (2)
C2—C1—C6—N1	179.1 (3)	O1—C9—C10—C11	132.2 (3)
C4—C5—C6—C1	−0.4 (4)	N3—C9—C10—C11	−51.1 (4)
C4—C5—C6—N1	−179.0 (3)	O1—C9—C10—C15	−47.6 (4)
C7—N1—C6—C1	149.1 (3)	N3—C9—C10—C15	129.2 (3)
C7—N1—C6—C5	−32.2 (4)	C15—C10—C11—C12	−2.2 (4)
N3—N2—C7—N1	179.3 (2)	C9—C10—C11—C12	178.1 (3)
N3—N2—C7—S1	0.3 (3)	C10—C11—C12—C13	−0.9 (4)
C6—N1—C7—N2	−2.6 (5)	C16—O2—C13—C14	−8.4 (4)
C6—N1—C7—S1	176.4 (2)	C16—O2—C13—C12	171.9 (3)
C8—S1—C7—N2	−17.4 (2)	C11—C12—C13—O2	−177.5 (3)
C8—S1—C7—N1	163.5 (2)	C11—C12—C13—C14	2.8 (4)
C9—N3—C8—C18	−92.5 (3)	O2—C13—C14—C15	178.7 (3)
N2—N3—C8—C18	82.2 (3)	C12—C13—C14—C15	−1.6 (4)
C9—N3—C8—C17	36.5 (4)	C13—C14—C15—C10	−1.5 (4)
N2—N3—C8—C17	−148.8 (2)	C11—C10—C15—C14	3.4 (4)
C9—N3—C8—S1	151.9 (2)	C9—C10—C15—C14	−176.9 (2)
N2—N3—C8—S1	−33.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2	0.93	2.42	2.894 (4)	112
C11—H11···N2	0.93	2.51	2.828 (3)	100
C17—H17A···O1	0.96	2.40	2.832 (4)	107
N1—H1B···O1^i	0.85 (2)	2.12 (1)	2.923 (3)	160 (2)

Symmetry code: (i) −x+2, y−1/2, −z+1/2.