3-(2-Bromo­eth­yl)-5,5-di­phenyl­imidazolidine-2,4-dione

The imidazolidine ring in the title mol­ecule, C₁₇H₁₅BrN₂O₂, is slightly ruffled [r.m.s. deviation = 0.0192 Å], while the attached phenyl rings at the C atom at the position between the amine and carbonyl centres are rotated well out of its mean plane [dihedral angles with the imidazolidine ring = 63.60 (8) and 76.4 (1)°]. In the crystal, a three-dimensional network features N—H...O and C—H...O hydrogen bonds together with C—H...π(ring) inter­actions.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.052
• wR factor = 0.170
• Data-to-parameter ratio = 21.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C10 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         24 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXL2018/1 (Sheldrick, 2015b).

3-(2-Bromoethyl)-5,5-diphenylimidazolidine-2,4-dione

Crystal data

C17H15BrN2O2	F(000) = 728
Mr = 359.22	Dx = 1.446 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.7083 (5) Å	Cell parameters from 9961 reflections
b = 8.6500 (3) Å	θ = 2.3–27.3°
c = 14.1183 (5) Å	µ = 2.50 mm^−1
β = 99.724 (1)°	T = 298 K
V = 1650.05 (10) Å^3	Block, colourless
Z = 4	0.42 × 0.32 × 0.25 mm

Data collection

Bruker SMART APEX CCD diffractometer	4284 independent reflections
Radiation source: fine-focus sealed tube	3056 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 8.3333 pixels mm^-1	θmax = 28.8°, θmin = 1.9°
φ and ω scans	h = −18→17
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −11→11
Tmin = 0.46, Tmax = 0.58	l = −19→19
30580 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)] = 0.052	Hydrogen site location: mixed
wR(F^2) = 0.170	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0893P)^2 + 0.7858P] where P = (Fo^2 + 2Fc^2)/3
4284 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.82 e Å^−3
0 restraints	Δρmin = −0.67 e Å^−3

Special details

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 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 = 0.93 - 0.97 Å) while that attached to nitrogen was placed in a location derived from a difference map and its coordinates adjusted to give N—H = 0.89 %A. 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
Br1	0.42103 (4)	0.22083 (6)	0.82606 (3)	0.0970 (2)
O1	0.18452 (12)	0.1239 (2)	0.63926 (13)	0.0510 (4)
O2	0.48438 (13)	−0.0886 (2)	0.61836 (13)	0.0529 (4)
N1	0.33335 (14)	−0.0021 (2)	0.65056 (13)	0.0403 (4)
N2	0.37878 (14)	0.0634 (2)	0.51316 (14)	0.0424 (4)
H2	0.417288	0.072482	0.468641	0.051*
C1	0.28014 (15)	0.1311 (3)	0.50632 (15)	0.0361 (4)
C2	0.25666 (15)	0.0868 (3)	0.60614 (15)	0.0374 (4)
C3	0.40774 (16)	−0.0157 (3)	0.59400 (16)	0.0395 (5)
C4	0.3411 (2)	−0.0664 (3)	0.74680 (19)	0.0549 (6)
H4A	0.349683	−0.177478	0.743311	0.066*
H4B	0.279528	−0.047609	0.770075	0.066*
C5	0.4249 (3)	−0.0010 (5)	0.8179 (2)	0.0752 (9)
H5A	0.487132	−0.031874	0.799497	0.090*
H5B	0.422518	−0.044378	0.880776	0.090*
C6	0.20839 (17)	0.0547 (3)	0.42505 (16)	0.0412 (5)
C7	0.12239 (18)	−0.0173 (3)	0.4386 (2)	0.0513 (6)
H7	0.104522	−0.017699	0.499314	0.062*
C8	0.0619 (2)	−0.0895 (4)	0.3625 (3)	0.0659 (8)
H8	0.003723	−0.137210	0.372572	0.079*
C9	0.0871 (3)	−0.0910 (4)	0.2741 (3)	0.0803 (10)
H9	0.046718	−0.140238	0.223419	0.096*
C10	0.1722 (4)	−0.0197 (6)	0.2595 (3)	0.1016 (15)
H10	0.189448	−0.020397	0.198523	0.122*
C11	0.2333 (3)	0.0538 (5)	0.3343 (2)	0.0772 (10)
H11	0.290963	0.102283	0.323391	0.093*
C12	0.28154 (17)	0.3076 (3)	0.49925 (17)	0.0406 (5)
C13	0.3654 (2)	0.3905 (3)	0.5354 (3)	0.0680 (8)
H13	0.422881	0.338705	0.562487	0.082*
C14	0.3647 (3)	0.5504 (4)	0.5316 (3)	0.0851 (11)
H14	0.421780	0.605165	0.556105	0.102*
C15	0.2814 (3)	0.6282 (4)	0.4925 (3)	0.0778 (10)
H15	0.281492	0.735614	0.489416	0.093*
C16	0.1985 (3)	0.5476 (4)	0.4581 (3)	0.0750 (9)
H16	0.141001	0.600601	0.432518	0.090*
C17	0.1975 (2)	0.3870 (3)	0.4603 (2)	0.0598 (7)
H17	0.140013	0.333439	0.435486	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.1041 (4)	0.0862 (3)	0.0912 (3)	−0.0175 (2)	−0.0107 (2)	−0.0181 (2)
O1	0.0413 (9)	0.0627 (11)	0.0519 (9)	0.0039 (8)	0.0162 (7)	−0.0076 (8)
O2	0.0477 (9)	0.0542 (10)	0.0584 (10)	0.0179 (8)	0.0137 (8)	0.0165 (8)
N1	0.0412 (9)	0.0405 (10)	0.0407 (9)	0.0009 (7)	0.0112 (7)	0.0045 (8)
N2	0.0378 (9)	0.0478 (11)	0.0440 (10)	0.0112 (8)	0.0138 (7)	0.0076 (8)
C1	0.0328 (9)	0.0361 (10)	0.0399 (10)	0.0045 (8)	0.0074 (8)	−0.0002 (8)
C2	0.0359 (10)	0.0365 (11)	0.0402 (10)	−0.0016 (8)	0.0076 (8)	−0.0051 (8)
C3	0.0393 (11)	0.0347 (11)	0.0458 (11)	0.0024 (8)	0.0108 (9)	0.0030 (9)
C4	0.0610 (15)	0.0567 (15)	0.0492 (13)	−0.0017 (12)	0.0155 (11)	0.0142 (12)
C5	0.080 (2)	0.088 (3)	0.0543 (16)	0.0110 (17)	0.0019 (15)	0.0095 (16)
C6	0.0456 (11)	0.0348 (11)	0.0421 (11)	0.0037 (9)	0.0038 (9)	−0.0017 (9)
C7	0.0402 (11)	0.0536 (14)	0.0587 (14)	0.0015 (10)	0.0038 (10)	−0.0107 (12)
C8	0.0479 (14)	0.0576 (17)	0.086 (2)	−0.0004 (12)	−0.0069 (13)	−0.0180 (15)
C9	0.089 (2)	0.072 (2)	0.069 (2)	−0.0047 (18)	−0.0169 (17)	−0.0243 (17)
C10	0.127 (3)	0.131 (4)	0.0463 (17)	−0.038 (3)	0.0114 (19)	−0.022 (2)
C11	0.095 (2)	0.092 (2)	0.0469 (15)	−0.032 (2)	0.0203 (15)	−0.0127 (16)
C12	0.0421 (11)	0.0354 (11)	0.0438 (11)	0.0011 (8)	0.0055 (9)	−0.0012 (9)
C13	0.0529 (15)	0.0466 (15)	0.095 (2)	−0.0047 (12)	−0.0158 (14)	0.0038 (14)
C14	0.077 (2)	0.0505 (17)	0.117 (3)	−0.0192 (16)	−0.015 (2)	−0.0067 (18)
C15	0.094 (2)	0.0365 (14)	0.100 (3)	−0.0010 (15)	0.007 (2)	−0.0063 (15)
C16	0.0706 (19)	0.0417 (15)	0.107 (3)	0.0166 (14)	−0.0011 (18)	0.0032 (16)
C17	0.0461 (13)	0.0425 (13)	0.085 (2)	0.0069 (10)	−0.0042 (13)	−0.0032 (13)

Geometric parameters (Å, º)

Br1—C5	1.923 (4)	C7—H7	0.9300
O1—C2	1.207 (3)	C8—C9	1.351 (5)
O2—C3	1.223 (3)	C8—H8	0.9300
N1—C2	1.366 (3)	C9—C10	1.366 (6)
N1—C3	1.402 (3)	C9—H9	0.9300
N1—C4	1.455 (3)	C10—C11	1.386 (5)
N2—C3	1.333 (3)	C10—H10	0.9300
N2—C1	1.461 (3)	C11—H11	0.9300
N2—H2	0.8899	C12—C17	1.374 (3)
C1—C6	1.529 (3)	C12—C13	1.378 (4)
C1—C12	1.530 (3)	C13—C14	1.384 (5)
C1—C2	1.546 (3)	C13—H13	0.9300
C4—C5	1.502 (5)	C14—C15	1.360 (5)
C4—H4A	0.9700	C14—H14	0.9300
C4—H4B	0.9700	C15—C16	1.352 (5)
C5—H5A	0.9700	C15—H15	0.9300
C5—H5B	0.9700	C16—C17	1.389 (4)
C6—C7	1.375 (4)	C16—H16	0.9300
C6—C11	1.381 (4)	C17—H17	0.9300
C7—C8	1.390 (4)
C2—N1—C3	111.28 (18)	C6—C7—C8	120.6 (3)
C2—N1—C4	125.0 (2)	C6—C7—H7	119.7
C3—N1—C4	123.6 (2)	C8—C7—H7	119.7
C3—N2—C1	113.63 (18)	C9—C8—C7	120.5 (3)
C3—N2—H2	121.6	C9—C8—H8	119.8
C1—N2—H2	124.8	C7—C8—H8	119.8
N2—C1—C6	110.32 (18)	C8—C9—C10	119.5 (3)
N2—C1—C12	112.45 (18)	C8—C9—H9	120.2
C6—C1—C12	113.30 (17)	C10—C9—H9	120.2
N2—C1—C2	99.99 (16)	C9—C10—C11	120.9 (3)
C6—C1—C2	111.75 (18)	C9—C10—H10	119.5
C12—C1—C2	108.26 (17)	C11—C10—H10	119.5
O1—C2—N1	126.1 (2)	C6—C11—C10	119.8 (3)
O1—C2—C1	126.7 (2)	C6—C11—H11	120.1
N1—C2—C1	107.18 (17)	C10—C11—H11	120.1
O2—C3—N2	128.5 (2)	C17—C12—C13	118.6 (2)
O2—C3—N1	123.8 (2)	C17—C12—C1	120.4 (2)
N2—C3—N1	107.71 (18)	C13—C12—C1	120.9 (2)
N1—C4—C5	114.0 (2)	C12—C13—C14	120.4 (3)
N1—C4—H4A	108.8	C12—C13—H13	119.8
C5—C4—H4A	108.8	C14—C13—H13	119.8
N1—C4—H4B	108.8	C15—C14—C13	120.7 (3)
C5—C4—H4B	108.8	C15—C14—H14	119.6
H4A—C4—H4B	107.7	C13—C14—H14	119.6
C4—C5—Br1	113.0 (2)	C16—C15—C14	119.2 (3)
C4—C5—H5A	109.0	C16—C15—H15	120.4
Br1—C5—H5A	109.0	C14—C15—H15	120.4
C4—C5—H5B	109.0	C15—C16—C17	121.2 (3)
Br1—C5—H5B	109.0	C15—C16—H16	119.4
H5A—C5—H5B	107.8	C17—C16—H16	119.4
C7—C6—C11	118.6 (2)	C12—C17—C16	119.9 (3)
C7—C6—C1	123.3 (2)	C12—C17—H17	120.1
C11—C6—C1	118.0 (2)	C16—C17—H17	120.1
C3—N2—C1—C6	−113.5 (2)	N2—C1—C6—C11	−54.9 (3)
C3—N2—C1—C12	119.0 (2)	C12—C1—C6—C11	72.1 (3)
C3—N2—C1—C2	4.3 (2)	C2—C1—C6—C11	−165.2 (3)
C3—N1—C2—O1	−176.7 (2)	C11—C6—C7—C8	0.0 (4)
C4—N1—C2—O1	−0.6 (4)	C1—C6—C7—C8	−177.7 (2)
C3—N1—C2—C1	3.1 (2)	C6—C7—C8—C9	0.4 (5)
C4—N1—C2—C1	179.1 (2)	C7—C8—C9—C10	−0.6 (6)
N2—C1—C2—O1	175.5 (2)	C8—C9—C10—C11	0.2 (7)
C6—C1—C2—O1	−67.8 (3)	C7—C6—C11—C10	−0.4 (6)
C12—C1—C2—O1	57.7 (3)	C1—C6—C11—C10	177.4 (4)
N2—C1—C2—N1	−4.3 (2)	C9—C10—C11—C6	0.3 (7)
C6—C1—C2—N1	112.5 (2)	N2—C1—C12—C17	157.7 (2)
C12—C1—C2—N1	−122.08 (19)	C6—C1—C12—C17	31.7 (3)
C1—N2—C3—O2	177.4 (2)	C2—C1—C12—C17	−92.8 (3)
C1—N2—C3—N1	−2.8 (3)	N2—C1—C12—C13	−25.2 (3)
C2—N1—C3—O2	179.4 (2)	C6—C1—C12—C13	−151.1 (3)
C4—N1—C3—O2	3.3 (4)	C2—C1—C12—C13	84.3 (3)
C2—N1—C3—N2	−0.4 (3)	C17—C12—C13—C14	−0.5 (5)
C4—N1—C3—N2	−176.5 (2)	C1—C12—C13—C14	−177.7 (3)
C2—N1—C4—C5	−113.9 (3)	C12—C13—C14—C15	0.1 (7)
C3—N1—C4—C5	61.7 (4)	C13—C14—C15—C16	0.8 (7)
N1—C4—C5—Br1	55.0 (3)	C14—C15—C16—C17	−1.3 (7)
N2—C1—C6—C7	122.8 (2)	C13—C12—C17—C16	0.0 (5)
C12—C1—C6—C7	−110.1 (3)	C1—C12—C17—C16	177.2 (3)
C2—C1—C6—C7	12.5 (3)	C15—C16—C17—C12	0.9 (6)

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the C12–C17 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2^i	0.89	1.98	2.862 (3)	174
C4—H4A···O1^ii	0.97	2.49	3.175 (3)	128
C8—H8···O1^iii	0.93	2.56	3.387 (3)	148
C10—H10···Cg3^iv	0.93	2.85	3.771 (5)	173

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