3-Methyl-2-(methyl­sulfan­yl)-5,5-diphenyl-3,5-di­hydro-4H-imidazol-4-one

In the title mol­ecule, C₁₇H₁₆N₂OS, the di­hydro­imidazolone ring is slightly puckered and the methyl­sulfanyl group is nearly coplanar with it. In the crystal, two sets of C—H...O hydrogen bonds form corrugated layers of mol­ecules parallel to the ac plane. The layers pack with normal van der Waals contacts between them.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.080
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          6 Note

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 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
   2 ALERT level G = General information/check it is not something unexpected

   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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX4 (Bruker, 2021); cell refinement: SAINT (Bruker, 2021); data reduction: SAINT (Bruker, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-Methyl-2-(methylsulfanyl)-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one

Crystal data

C17H16N2OS	F(000) = 624
Mr = 296.38	Dx = 1.326 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 8.4129 (1) Å	Cell parameters from 9855 reflections
b = 22.9217 (4) Å	θ = 3.9–72.4°
c = 8.6719 (1) Å	µ = 1.93 mm^−1
β = 117.417 (1)°	T = 150 K
V = 1484.44 (4) Å^3	Plate, colourless
Z = 4	0.20 × 0.06 × 0.03 mm

Data collection

Bruker D8 VENTURE PHOTON 3 CPAD diffractometer	2930 independent reflections
Radiation source: INCOATEC IµS micro—-focus source	2733 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
Detector resolution: 7.3910 pixels mm^-1	θmax = 72.4°, θmin = 3.9°
φ and ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −28→28
Tmin = 0.85, Tmax = 0.94	l = −10→10
37955 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.040P)^2 + 0.6009P] where P = (Fo^2 + 2Fc^2)/3
2930 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. The diffraction data were obtained from 15 sets of frames, each of width 0.5° in ω or φ, collected with scan parameters determined by the "strategy" routine in APEX4. The scan time was θ-dependent and ranged from 5 to 15 sec/frame.

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.

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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	Uiso*/Ueq
S1	0.72407 (4)	0.53586 (2)	1.16914 (4)	0.02823 (11)
O1	0.54051 (12)	0.71912 (4)	0.82460 (12)	0.0271 (2)
N1	0.61671 (14)	0.63912 (5)	1.00499 (13)	0.0236 (2)
N2	0.70761 (14)	0.57313 (4)	0.86599 (13)	0.0217 (2)
C1	0.64968 (16)	0.62639 (5)	0.75658 (15)	0.0202 (2)
C2	0.59464 (16)	0.66941 (5)	0.86029 (16)	0.0216 (2)
C3	0.68352 (15)	0.58379 (5)	0.99846 (15)	0.0216 (2)
C4	0.80769 (16)	0.64949 (5)	0.73319 (16)	0.0219 (3)
C5	0.92075 (18)	0.69236 (6)	0.84133 (18)	0.0305 (3)
H5	0.896928	0.709387	0.928442	0.037*
C6	1.0688 (2)	0.71050 (7)	0.8226 (2)	0.0369 (3)
H6	1.145882	0.739664	0.897666	0.044*
C7	1.10450 (18)	0.68648 (7)	0.69606 (19)	0.0346 (3)
H7	1.205289	0.699222	0.683353	0.041*
C8	0.99264 (19)	0.64370 (6)	0.58764 (18)	0.0321 (3)
H8	1.016772	0.626991	0.500337	0.039*
C9	0.84503 (17)	0.62513 (6)	0.60624 (17)	0.0260 (3)
H9	0.769091	0.595615	0.531833	0.031*
C10	0.48418 (16)	0.61446 (5)	0.58351 (15)	0.0209 (2)
C11	0.39872 (18)	0.56066 (6)	0.54725 (17)	0.0273 (3)
H11	0.443592	0.530142	0.630553	0.033*
C12	0.24745 (19)	0.55132 (6)	0.38914 (19)	0.0337 (3)
H12	0.190002	0.514342	0.364685	0.040*
C13	0.18031 (17)	0.59563 (6)	0.26740 (17)	0.0301 (3)
H13	0.076931	0.589203	0.159682	0.036*
C14	0.26501 (17)	0.64947 (6)	0.30376 (17)	0.0277 (3)
H14	0.218962	0.680058	0.220802	0.033*
C15	0.41649 (17)	0.65893 (6)	0.46046 (16)	0.0249 (3)
H15	0.474305	0.695842	0.484019	0.030*
C16	0.5778 (2)	0.66282 (7)	1.13960 (19)	0.0364 (3)
H16A	0.690265	0.671538	1.243296	0.055*
H16B	0.509363	0.634189	1.168803	0.055*
H16C	0.507500	0.698691	1.097364	0.055*
C17	0.7916 (2)	0.47276 (6)	1.0905 (2)	0.0348 (3)
H17A	0.700908	0.464056	0.971597	0.052*
H17B	0.804208	0.439295	1.165589	0.052*
H17C	0.906603	0.480549	1.091373	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.03234 (19)	0.03103 (18)	0.02251 (17)	0.00075 (12)	0.01364 (14)	0.00651 (12)
O1	0.0333 (5)	0.0212 (4)	0.0296 (5)	0.0024 (4)	0.0169 (4)	−0.0003 (4)
N1	0.0283 (5)	0.0254 (5)	0.0210 (5)	0.0013 (4)	0.0146 (4)	−0.0003 (4)
N2	0.0236 (5)	0.0217 (5)	0.0209 (5)	0.0003 (4)	0.0112 (4)	0.0020 (4)
C1	0.0232 (6)	0.0197 (5)	0.0202 (6)	0.0001 (4)	0.0120 (5)	0.0006 (4)
C2	0.0207 (6)	0.0239 (6)	0.0210 (6)	−0.0026 (5)	0.0102 (5)	−0.0018 (5)
C3	0.0201 (6)	0.0240 (6)	0.0206 (6)	−0.0016 (4)	0.0092 (5)	0.0011 (5)
C4	0.0213 (6)	0.0249 (6)	0.0199 (6)	0.0016 (4)	0.0098 (5)	0.0046 (5)
C5	0.0308 (7)	0.0374 (7)	0.0256 (6)	−0.0069 (6)	0.0150 (6)	−0.0020 (5)
C6	0.0305 (7)	0.0444 (8)	0.0340 (8)	−0.0126 (6)	0.0132 (6)	0.0001 (6)
C7	0.0235 (6)	0.0466 (8)	0.0359 (8)	0.0009 (6)	0.0157 (6)	0.0139 (6)
C8	0.0300 (7)	0.0418 (8)	0.0312 (7)	0.0081 (6)	0.0199 (6)	0.0080 (6)
C9	0.0262 (6)	0.0292 (6)	0.0250 (6)	0.0030 (5)	0.0137 (5)	0.0022 (5)
C10	0.0216 (6)	0.0239 (6)	0.0208 (6)	0.0007 (4)	0.0130 (5)	−0.0014 (4)
C11	0.0279 (6)	0.0237 (6)	0.0297 (7)	−0.0007 (5)	0.0129 (5)	0.0006 (5)
C12	0.0295 (7)	0.0294 (7)	0.0371 (8)	−0.0057 (5)	0.0111 (6)	−0.0065 (6)
C13	0.0231 (6)	0.0398 (7)	0.0250 (6)	0.0013 (5)	0.0090 (5)	−0.0068 (5)
C14	0.0274 (7)	0.0334 (7)	0.0229 (6)	0.0056 (5)	0.0122 (5)	0.0030 (5)
C15	0.0280 (6)	0.0246 (6)	0.0245 (6)	−0.0005 (5)	0.0141 (5)	0.0003 (5)
C16	0.0501 (9)	0.0395 (8)	0.0285 (7)	0.0082 (6)	0.0257 (7)	−0.0008 (6)
C17	0.0381 (8)	0.0278 (7)	0.0356 (8)	0.0051 (6)	0.0145 (6)	0.0074 (6)

Geometric parameters (Å, º)

S1—C3	1.7461 (12)	C8—H8	0.9500
S1—C17	1.7995 (15)	C9—H9	0.9500
O1—C2	1.2130 (15)	C10—C11	1.3887 (17)
N1—C2	1.3699 (16)	C10—C15	1.3937 (17)
N1—C3	1.3991 (16)	C11—C12	1.3922 (19)
N1—C16	1.4550 (16)	C11—H11	0.9500
N2—C3	1.2786 (16)	C12—C13	1.384 (2)
N2—C1	1.4840 (15)	C12—H12	0.9500
C1—C4	1.5287 (16)	C13—C14	1.387 (2)
C1—C10	1.5302 (16)	C13—H13	0.9500
C1—C2	1.5426 (16)	C14—C15	1.3867 (19)
C4—C5	1.3888 (18)	C14—H14	0.9500
C4—C9	1.3932 (18)	C15—H15	0.9500
C5—C6	1.391 (2)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.379 (2)	C16—H16C	0.9800
C6—H6	0.9500	C17—H17A	0.9800
C7—C8	1.384 (2)	C17—H17B	0.9800
C7—H7	0.9500	C17—H17C	0.9800
C8—C9	1.3907 (19)
C3—S1—C17	99.02 (6)	C8—C9—H9	119.8
C2—N1—C3	108.05 (10)	C4—C9—H9	119.8
C2—N1—C16	124.06 (11)	C11—C10—C15	119.33 (12)
C3—N1—C16	127.88 (11)	C11—C10—C1	121.54 (11)
C3—N2—C1	106.02 (10)	C15—C10—C1	119.12 (11)
N2—C1—C4	108.67 (9)	C10—C11—C12	120.18 (12)
N2—C1—C10	111.27 (9)	C10—C11—H11	119.9
C4—C1—C10	112.70 (10)	C12—C11—H11	119.9
N2—C1—C2	104.57 (9)	C13—C12—C11	120.34 (13)
C4—C1—C2	111.64 (10)	C13—C12—H12	119.8
C10—C1—C2	107.71 (9)	C11—C12—H12	119.8
O1—C2—N1	125.90 (11)	C12—C13—C14	119.54 (12)
O1—C2—C1	129.05 (11)	C12—C13—H13	120.2
N1—C2—C1	105.04 (10)	C14—C13—H13	120.2
N2—C3—N1	116.26 (11)	C15—C14—C13	120.41 (12)
N2—C3—S1	126.26 (10)	C15—C14—H14	119.8
N1—C3—S1	117.47 (9)	C13—C14—H14	119.8
C5—C4—C9	118.93 (12)	C14—C15—C10	120.20 (12)
C5—C4—C1	121.51 (11)	C14—C15—H15	119.9
C9—C4—C1	119.49 (11)	C10—C15—H15	119.9
C4—C5—C6	120.28 (13)	N1—C16—H16A	109.5
C4—C5—H5	119.9	N1—C16—H16B	109.5
C6—C5—H5	119.9	H16A—C16—H16B	109.5
C7—C6—C5	120.55 (14)	N1—C16—H16C	109.5
C7—C6—H6	119.7	H16A—C16—H16C	109.5
C5—C6—H6	119.7	H16B—C16—H16C	109.5
C6—C7—C8	119.62 (13)	S1—C17—H17A	109.5
C6—C7—H7	120.2	S1—C17—H17B	109.5
C8—C7—H7	120.2	H17A—C17—H17B	109.5
C7—C8—C9	120.14 (13)	S1—C17—H17C	109.5
C7—C8—H8	119.9	H17A—C17—H17C	109.5
C9—C8—H8	119.9	H17B—C17—H17C	109.5
C8—C9—C4	120.49 (13)
C3—N2—C1—C4	121.22 (11)	C10—C1—C4—C9	−41.41 (15)
C3—N2—C1—C10	−114.13 (11)	C2—C1—C4—C9	−162.79 (11)
C3—N2—C1—C2	1.88 (12)	C9—C4—C5—C6	0.0 (2)
C3—N1—C2—O1	−179.29 (12)	C1—C4—C5—C6	176.77 (12)
C16—N1—C2—O1	−0.1 (2)	C4—C5—C6—C7	0.4 (2)
C3—N1—C2—C1	1.68 (12)	C5—C6—C7—C8	−0.4 (2)
C16—N1—C2—C1	−179.13 (12)	C6—C7—C8—C9	0.1 (2)
N2—C1—C2—O1	178.84 (12)	C7—C8—C9—C4	0.3 (2)
C4—C1—C2—O1	61.52 (16)	C5—C4—C9—C8	−0.33 (19)
C10—C1—C2—O1	−62.70 (16)	C1—C4—C9—C8	−177.20 (12)
N2—C1—C2—N1	−2.18 (12)	N2—C1—C10—C11	4.07 (15)
C4—C1—C2—N1	−119.50 (11)	C4—C1—C10—C11	126.43 (12)
C10—C1—C2—N1	116.28 (10)	C2—C1—C10—C11	−109.99 (12)
C1—N2—C3—N1	−0.95 (14)	N2—C1—C10—C15	−176.77 (10)
C1—N2—C3—S1	178.44 (9)	C4—C1—C10—C15	−54.41 (14)
C2—N1—C3—N2	−0.54 (15)	C2—C1—C10—C15	69.17 (13)
C16—N1—C3—N2	−179.68 (13)	C15—C10—C11—C12	0.28 (19)
C2—N1—C3—S1	−179.98 (8)	C1—C10—C11—C12	179.44 (12)
C16—N1—C3—S1	0.87 (18)	C10—C11—C12—C13	−0.4 (2)
C17—S1—C3—N2	−2.75 (13)	C11—C12—C13—C14	0.1 (2)
C17—S1—C3—N1	176.63 (10)	C12—C13—C14—C15	0.3 (2)
N2—C1—C4—C5	−94.40 (14)	C13—C14—C15—C10	−0.50 (19)
C10—C1—C4—C5	141.79 (12)	C11—C10—C15—C14	0.19 (18)
C2—C1—C4—C5	20.42 (16)	C1—C10—C15—C14	−178.99 (11)
N2—C1—C4—C9	82.39 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1^i	0.95	2.55	3.390 (2)	148
C15—H15···O1^ii	0.95	2.59	3.3797 (17)	140

Symmetry codes: (i) x+1, y, z; (ii) x, −y+3/2, z−1/2.